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WO2019225938A1 - Compound and organic light emitting diode comprising same - Google Patents

Compound and organic light emitting diode comprising same Download PDF

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Publication number
WO2019225938A1
WO2019225938A1 PCT/KR2019/006050 KR2019006050W WO2019225938A1 WO 2019225938 A1 WO2019225938 A1 WO 2019225938A1 KR 2019006050 W KR2019006050 W KR 2019006050W WO 2019225938 A1 WO2019225938 A1 WO 2019225938A1
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group
substituted
unsubstituted
formula
compound
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PCT/KR2019/006050
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French (fr)
Korean (ko)
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김경희
김명곤
홍완표
이동훈
김동헌
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주식회사 엘지화학
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Priority to CN201980010697.1A priority Critical patent/CN111655697B/en
Publication of WO2019225938A1 publication Critical patent/WO2019225938A1/en

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention provides a compound represented by Formula 1 and an organic light emitting device including the same.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer has a multi-layered structure composed of different materials in order to increase efficiency and stability of the organic light emitting device.
  • the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • the present specification is intended to provide an organic light emitting device having a low driving voltage, high luminous efficiency, good lifespan characteristics, or high color purity by including a compound represented by Chemical Formula 1.
  • An exemplary embodiment of the present specification provides a compound represented by the following Formula 1.
  • X is O, S or Si (R1) (R2),
  • R1 and R2 are the same as or different from each other, and each independently hydrogen, an alkyl group or an aryl group,
  • Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • the substituent in the "substituted or unsubstituted” is deuterium; Halogen group; A chain alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group unsubstituted or substituted with deuterium; Haloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An aryl group unsubstituted or substituted with deuterium; Or a heteroaryl group unsubstituted or substituted with deuterium,
  • n 0 or 1
  • An exemplary embodiment of the present specification includes a first electrode; Second electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes the compound represented by Chemical Formula 1 described above.
  • the compound described herein may be used as a material of the organic material layer of the organic light emitting device.
  • the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport or luminescent materials.
  • the organic light emitting device including the compound of the present invention may be improved in efficiency.
  • the organic light emitting device including the compound of the present invention may have a low driving voltage.
  • the organic light emitting device including the compound of the present invention may have improved lifetime characteristics.
  • FIG. 1 illustrates an example of an organic light emitting device including a substrate 1, an anode 2, an organic material layer 3, and a cathode 4.
  • FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a hole control layer 7, a light emitting layer 8, an electron transport layer 9, an electron injection layer 10.
  • an organic light emitting element composed of a cathode 4.
  • FIG. 3 shows a substrate 1, an anode 2, a hole injection layer 5, a first hole transport layer 6a, a second hole transport layer 6b, a light emitting layer 8, an electron injection and transport layer 11, and a cathode.
  • the example of the organic light emitting element which consists of (4) is shown.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent.
  • the position at which the substituent is substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position at which the substituent is substituted.
  • substituents are two or more, two or more substituents may be the same or different from each other.
  • substituted or unsubstituted is deuterium; Halogen group; Nitrile group; Nitro group; An alkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Phosphine oxide groups unsubstituted or substituted with alkyl or aryl groups; Aryl group; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group, or substituted or unsubstituted with a group to which two substituents of the substituents exemplified above.
  • the meaning of being substituted with A or B includes all substituted with 1 or 2 or more A, substituted with 1 or 2 or more B, or substituted together with 1 or 2 or more A and 1 or 2 or more B. do.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the silyl group is -SiH 3
  • the silyl group may be substituted or unsubstituted with an alkyl group or an aryl group.
  • the silyl group unsubstituted or substituted with the alkyl group or the aryl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, Phenylsilyl group and the like, but is not limited thereto.
  • the alkylsilyl group means a silyl group substituted with an alkyl group
  • the arylsilyl group means a silyl group substituted with an aryl group
  • an alkyl group means a straight or branched chain saturated hydrocarbon. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • the alkyl group may be chain or cyclic.
  • chain alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, n-octyl, tert -Octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2,2-
  • Carbon number of the cyclic alkyl group is not particularly limited, but according to one embodiment, the carbon number of the cycloalkyl group is 3 to 14. According to another exemplary embodiment, the cycloalkyl group has 3 to 8 carbon atoms. Specific examples of the cycloalkyl group include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclooctyl, and the like.
  • an aryl group means a substituted or unsubstituted monocyclic or polycyclic which is wholly or partially unsaturated.
  • the aryl group has 6 to 30 carbon atoms.
  • the aryl group may be a monocyclic aryl group or a polycyclic aryl group. Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, and a terphenyl group, but are not limited thereto.
  • polycyclic aryl group a naphthyl group, anthracenyl group, a phenanthrenyl group, a perrylenyl group, a fluoranthenyl group, a triphenylenyl group, a penalenyl group, a pyrenyl group, a tetrasenyl group, a chrysenyl group, a pentaxenyl group , Fluorenyl group, indenyl group, acenaphthyl group, benzofluorenyl group, spirobifluorenyl group and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the heteroaryl group is a ring group containing one or more of N, O and S as heteroatoms, and carbon number is not particularly limited, but is 2 to 40. According to another exemplary embodiment, the heteroaryl group has 2 to 30 carbon atoms.
  • heteroaryl group examples include thiophenyl group, furanyl group, pyrrolyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridinyl group, bipyridinyl group, pyrimidinyl group, triazinyl group, tria Sleepyl group, acridinyl group, carbolinyl group, acenaphthoquinoxalinyl group, indenoquinazolinyl group, indenoisoquinolinyl group, indenoquinolinyl group, pyridoindolyl group, pyridazinyl group, pyrazinyl group, Quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group,
  • An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1.
  • the compound of the present invention has a structure in which benzofuran, benzothiophene, benzosilol, naphthofuran, naphthothiophene or naphthosilol is condensed in a benzene ring of naphtho [2,3-b] benzofuran as a core structure. Since the LUMO energy level of the compound is lowered due to the core structure, when the compound of the present invention is used as a dopant material of the light emitting layer, energy transfer from the host material of the light emitting layer to the compound of the present invention is easy.
  • the overlap of the HOMO energy level and the LUMO energy level is increased due to the core structure of the compound of the present invention, and thus the emission efficiency of the device can be improved by increasing the radiation transfer probability.
  • the radiation transition probability (Oscillator strength) is increased compared to the structure containing no amine group or one amine group, thereby increasing the luminous efficiency of the device.
  • R1 and R2 are the same as or different from each other, and are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 24 carbon atoms.
  • R1 and R2 are the same as or different from each other, and are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 18 carbon atoms.
  • R1 and R2 are the same as or different from each other, and are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms.
  • R1 and R2 are the same as or different from each other, and are each independently hydrogen, a methyl group, or a phenyl group.
  • At least one of Ar1 and Ar2 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • At least one of Ar1 and Ar2 is a substituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • At least one of Ar3 and Ar4 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • At least one of Ar3 and Ar4 is a substituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • Ar1 to Ar4 are the same as or different from each other, and each independently a cycloalkyl group unsubstituted or substituted with one or two or more substituents; An aryl group unsubstituted or substituted with one or two or more substituents; Or a heteroaryl group unsubstituted or substituted with one or two or more substituents, and the substituent in 'substituted or unsubstituted' is deuterium; Halogen group; A chain alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group unsubstituted or substituted with deuterium; Haloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An aryl group unsubstituted or substituted with deuterium; Or a heteroaryl group unsubstituted or substituted with deuterium.
  • Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms; Substituted or unsubstituted aryl group having 6 to 25 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, the substituent in the "substituted or unsubstituted” is deuterium; Halogen group; A chain alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group unsubstituted or substituted with deuterium; Haloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An aryl group unsubstituted or substituted with deuterium; Or a heteroaryl group unsubstituted or substituted with deuterium.
  • Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms; Substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, the substituent in the "substituted or unsubstituted” is deuterium; Halogen group; A chain alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group unsubstituted or substituted with deuterium; Haloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An aryl group unsubstituted or substituted with deuterium; Or a heteroaryl group unsubstituted or substituted with deuterium.
  • Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms; Substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 16 carbon atoms, the substituent in the "substituted or unsubstituted” is deuterium; Halogen group; A chain alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group unsubstituted or substituted with deuterium; Haloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An aryl group unsubstituted or substituted with deuterium; Or a heteroaryl group unsubstituted or substituted with deuterium.
  • Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted 1 to 4 ring aryl group; Or a substituted or unsubstituted 1 to 5 ring heteroaryl group, the substituent in the "substituted or unsubstituted” is deuterium; Halogen group; A chain alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group unsubstituted or substituted with deuterium; Haloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An aryl group unsubstituted or substituted with deuterium; Or a heteroaryl group unsubstituted or substituted with deuterium.
  • Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted 1 to 3 ring aryl group; Or a substituted or unsubstituted 1 to 4 ring heteroaryl group, the substituent in the "substituted or unsubstituted” is deuterium; Halogen group; A chain alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group unsubstituted or substituted with deuterium; Haloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An aryl group unsubstituted or substituted with deuterium; Or a heteroaryl group unsubstituted or substituted with deuterium.
  • Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted cyclohexyl group; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted thiophenyl group; Substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophenyl group; Substituted or unsubstituted carbazolyl group; A substituted or unsubstituted naphthobenzofuranyl group; A substituted or unsubstituted naphthobenzothiopheny
  • Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, the substituent in the "substituted or unsubstituted” is deuterium; Halogen group; C1-C6 linear alkyl group unsubstituted or substituted by deuterium; A cycloalkyl group having 3 to 8 carbon atoms unsubstituted or substituted with deuterium; Haloalkyl groups having 1 to 6 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 15 carbon atoms; An aryl group having 6 to 25 carbon atoms unsubstituted or substituted with deuterium; Or a heteroaryl group having
  • Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, the substituent in the "substituted or unsubstituted” is deuterium; Halogen group; C1-C6 linear alkyl group unsubstituted or substituted by deuterium; A cycloalkyl group having 3 to 6 carbon atoms unsubstituted or substituted with deuterium; Haloalkyl groups having 1 to 4 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 13 carbon atoms; An aryl group having 6 to 13 carbon atoms unsubstituted or substituted with deuterium; Or a heteroaryl group having
  • Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, the substituent in the "substituted or unsubstituted” is deuterium; Fluoro groups; Methyl group unsubstituted or substituted with deuterium; t-butyl group; Trifluoromethyl group; Trimethylsilyl group; A phenyl group unsubstituted or substituted with deuterium; Or a naphthyl group.
  • Ar1 to Ar4 are the same as or different from each other, and each independently a cyclohexyl group; Deuterium, fluoro group, phenyl group unsubstituted or substituted with methyl, t-butyl, trifluoromethyl, trimethylsilyl, phenyl or naphthyl groups unsubstituted or substituted with deuterium; Biphenyl group; Naphthyl group; 9,9-dimethyl fluorenyl group; Phenanthrenyl group; Thiophenyl group unsubstituted or substituted with a phenyl group; dibenzofuranyl group unsubstituted or substituted with a t-butyl group; Dibenzothiophenyl group; A carbazolyl group unsubstituted or substituted with a phenyl group unsubstituted or substituted with a methyl group, a phenyl group, or deuterium
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3.
  • One of X1 and X2 is a direct bond, the other is X,
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1 to 2-4.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 3-1 to 3-4.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 4-1 to 4-6.
  • the compound represented by Formula 1 is any one selected from the following compounds.
  • the compound represented by Formula 1 according to the present specification may be prepared according to the method of the following Formula 1.
  • R is an organic group.
  • Formula 1 is an example of a method of forming a compound represented by Formula 1, and the synthesis method of the compound represented by Formula 1 is not limited to the above Formula 1, by a method known in the art Can be.
  • the present specification provides an organic light emitting device including the compound represented by Chemical Formula 1.
  • An exemplary embodiment of the present specification provides an organic light emitting device including a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein the organic material layer is represented by Chemical Formula 1 It provides an organic light emitting device comprising a compound.
  • An exemplary embodiment of the present specification provides an organic light emitting device including a first electrode, a second electrode, and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers is the chemical formula It provides an organic light emitting device comprising the compound represented by 1.
  • An exemplary embodiment of the present specification is an organic light emitting device including a first electrode, a second electrode, and at least one organic material layer provided between the first electrode and the second electrode, wherein any one of the at least one organic material layer is provided.
  • the layer provides an organic light emitting device comprising the compound represented by Formula 1.
  • the organic material layer of the organic light emitting device of the present specification may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may be a hole injection layer, a hole transport layer, a layer for simultaneously transporting and injecting holes, a hole control layer, a light emitting layer, an electron control layer, an electron transport layer, an electron injection layer, an electron injection and transport as an organic material layer It may include a layer or the like.
  • the organic material layer includes a hole transport layer, a hole injection layer, a layer for simultaneously injecting and transporting holes or a hole control layer, and simultaneously performing the hole transporting layer, the hole injection layer, and the hole injection and transporting.
  • the layer or the hole control layer includes a compound represented by Chemical Formula 1. This means that at least one of the hole transport layer, the hole injection layer, the layer for simultaneously injecting and transporting the hole, and the hole control layer includes the compound represented by Chemical Formula 1.
  • the electron injection and transport layer is a layer that simultaneously performs electron injection and transport
  • the hole injection and transport layer is a layer that simultaneously performs hole injection and transport.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
  • the organic light emitting device may include two or more light emitting layers, and any one of the light emitting layers may include a compound represented by Chemical Formula 1.
  • the organic light emitting device may include two or more light emitting layers, and two or more layers may each independently include a compound represented by Chemical Formula 1.
  • two or more light emitting layers may be provided vertically or horizontally.
  • the compound represented by Formula 1 when the compound represented by Formula 1 is included in several organic material layers, the compound represented by Formula 1 included in each organic material layer may be the same or different from each other.
  • the organic light emitting device may include a plurality of light emitting layers, and each light emitting layer may have the same color or may have a different color from each other.
  • the light emitting layer including the compound represented by Formula 1 is a blue light emitting layer.
  • the organic light emitting diode is a blue organic light emitting diode including one light emitting layer including the compound represented by Chemical Formula 1.
  • the organic light emitting diode may further include a plurality of light emitting layers of red or green color in addition to the blue light emitting layer including the compound represented by Chemical Formula 1, in which case the organic light emitting white light is emitted.
  • the device may also be implemented.
  • the compound represented by Chemical Formula 1 is included as a dopant in the emission layer.
  • the light emitting layer includes a compound represented by Chemical Formula 1, and the light emitting layer further includes a compound represented by Chemical Formula H.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • R3 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted chain alkyl group; A substituted or unsubstituted cycloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Phosphine oxide groups unsubstituted or substituted with alkyl or aryl groups; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • a is an integer of 0-8, and when a is 2 or more, some R ⁇ 3> is the same or different from each other.
  • the light emitting layer is a compound represented by Chemical Formula 1; And one or two or more of the compounds represented by the above formula (H).
  • a plurality of compounds represented by Formula (H) may be the same as or different from each other.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 16 carbon atoms.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 12 carbon atoms.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 1 to 3 rings.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a monocyclic or bicyclic arylene group.
  • L1 and L2 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a naphthylene group.
  • Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 26 carbon atoms.
  • Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 22 carbon atoms.
  • Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 16 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms.
  • Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a heteroaryl group which is substituted or unsubstituted and includes N, O or S.
  • Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group containing at least one of pyrrole, furan, thiophene and pyridine.
  • Ar5 and Ar6 are the same as or different from each other, and each independently an aryl unsubstituted or substituted with deuterium, a chain alkyl group, a cycloalkyl group, an alkylsilyl group, a halogen group, a nitrile group, or an aryl group group; Or a heteroaryl group unsubstituted or substituted with an aryl group.
  • Ar5 and Ar6 are the same as or different from each other, and are each independently substituted or unsubstituted with deuterium, trimethylsilyl group, methyl group, cyclohexyl group, fluoro group, nitrile group, phenyl group or naphthyl group Ring aryl group; Or a heteroaryl group unsubstituted or substituted with a phenyl group.
  • Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted furanyl group; Substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophenyl group; A substituted or unsubstituted naphthobenzofuranyl group; A substituted or unsubstituted naphthobenzothiophenyl group; A substituted or unsubstituted indolocarbazolyl group; Or substituted or unsubstituted And X 11 and X 12 are each independently O or S.
  • a is 0.
  • R3 is hydrogen
  • Chemical Formula H is represented by the following Chemical Formula H-1 or Chemical Formula H-2.
  • L1, L2, R3 and a are the same as defined in formula H,
  • Ar7 to Ar9 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group,
  • HAr7 is a substituted or unsubstituted heteroaryl group.
  • Ar7 to Ar9 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms.
  • Ar7 to Ar9 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • Ar7 to Ar9 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 16 carbon atoms.
  • Ar7 to Ar9 are the same as or different from each other, and are each independently substituted or unsubstituted with deuterium, a chain alkyl group, a cycloalkyl group, an alkylsilyl group, a halogen group, a nitrile group or an aryl group It is.
  • Ar7 to Ar9 are the same as or different from each other, and are each independently substituted or unsubstituted with deuterium, trimethylsilyl, methyl, cyclohexyl, fluoro, nitrile, phenyl or naphthyl groups It is a substituted aryl group.
  • Ar7 to Ar9 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted phenanthrenyl group.
  • HAr7 is a substituted or unsubstituted heteroaryl group having 2 to 26 carbon atoms.
  • HAr7 is a substituted or unsubstituted C2-C22 heteroaryl group.
  • HAr7 is a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms.
  • HAr7 is a heteroaryl group which is substituted or unsubstituted and includes N, O or S.
  • HAr7 is a substituted or unsubstituted heteroaryl group including one or more of pyrrole, furan, thiophene and pyridine.
  • HAr7 is a heteroaryl group unsubstituted or substituted with an aryl group.
  • HAr7 is a heteroaryl group unsubstituted or substituted with a phenyl group.
  • HAr7 is a substituted or unsubstituted furanyl group; Substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophenyl group; A substituted or unsubstituted naphthobenzofuranyl group; A substituted or unsubstituted naphthobenzothiophenyl group; A substituted or unsubstituted indolocarbazolyl group; Or substituted or unsubstituted And X 11 and X 12 are each independently O or S.
  • the HAr7 is a furanyl group; Dibenzofuranyl group; Dibenzothiophenyl group; Naphthobenzofuranyl group; Naphthobenzothiophenyl group; Indolocarbazolyl group or And X 11 and X 12 are each independently O or S.
  • the light emitting layer includes a compound represented by Chemical Formula 1, and the light emitting layer further includes one or two or more compounds represented by Chemical Formula H-1.
  • the light emitting layer is a compound represented by Formula 1; And two compounds represented by Chemical Formula H-1.
  • the two compounds represented by Formula H-1 included in the emission layer may be the same or different from each other.
  • the light emitting layer is a compound represented by Formula 1; And one or two or more compounds represented by Formula H-2.
  • the light emitting layer is a compound represented by Formula 1; And two compounds represented by Formula H-2.
  • the two compounds represented by Formula H-2 included in the emission layer may be the same or different from each other.
  • the light emitting layer is a compound represented by Chemical Formula 1; At least one compound represented by Formula H-1; And one or more compounds represented by Formula H-2.
  • the light emitting layer is a compound represented by Chemical Formula 1; A compound represented by Chemical Formula H-1; And a compound represented by Chemical Formula H-2.
  • the compound represented by Formula H is any one selected from the following compounds.
  • the light emitting layer includes a compound represented by Formula 1, and the content of the compound represented by Formula 1 is 0.1 part by weight or more and 15 parts by weight or less with respect to 100 parts by weight of the total light emitting layer.
  • the light emitting layer includes a compound represented by Formula 1, and the content of the compound represented by Formula 1 is 0.1 part by weight or more and 10 parts by weight or less with respect to 100 parts by weight of the total light emitting layer.
  • the light emitting layer is 0.1 to 15 parts by weight of the compound represented by Formula 1; And 85 parts by weight to 99.9 parts by weight of the compound represented by Formula H.
  • the organic light emitting device may be an organic light emitting device having a normal structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an organic light emitting device having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is an anode.
  • FIGS. 1 to 3 The structure of the organic light emitting device according to the exemplary embodiment of the present specification is illustrated in FIGS. 1 to 3.
  • an organic light emitting diode may include a substrate 1, an anode 2, an organic material layer 3, and a cathode 4.
  • the compound represented by Formula 1 is included in the organic material layer (3).
  • the organic light emitting diode includes a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a hole control layer 7, and a light emitting layer. 8, the electron transport layer 9, the electron injection layer 10 and the cathode (4).
  • the compound represented by Formula 1 is included in the light emitting layer (8). In another embodiment, the compound represented by Formula 1 is included in any one of the hole transport layer 5, the hole transport layer 6 and the hole control layer (7).
  • FIG. 3 shows a substrate 1, an anode 2, a hole injection layer 5, a first hole transport layer 6a, a second hole transport layer 6b, a light emitting layer 8, an electron injection and transport layer 11, and a cathode.
  • the example of the organic light emitting element which consists of (4) is shown.
  • the compound represented by Formula 1 is included in the light emitting layer (8).
  • the structure of the organic light emitting diode according to the exemplary embodiment of the present specification is not limited to FIGS. 1 to 3, and may be any one of the following structures.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD, physical vapor deposition) such as sputtering (e-beam evaporation), by depositing a metal or conductive metal oxide or alloys thereof on the substrate It can be prepared by forming an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • PVD physical vapor deposition
  • sputtering e-beam evaporation
  • the compound represented by Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890).
  • the manufacturing method is not limited thereto.
  • the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes received from the electrode into the light emitting layer or an adjacent layer provided toward the light emitting layer.
  • the hole injection material has the ability to transport holes, has an effect of hole injection at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and transfers excitons generated from the light emitting layer to the electron injection layer or the electron injection material. It is preferable to use the compound which prevents and is excellent in thin film formation ability.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene Organic, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from an anode or a hole injection layer and transports holes to the light emitting layer.
  • a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable.
  • Specific examples of the hole transport material include, but are not limited to, an arylamine-based organic material, a conductive polymer, a block copolymer having a conjugated portion and a non-conjugated portion together, and the like.
  • the hole control layer is a layer for preventing the flow of the electrons to the anode to the light emitting layer and to control the flow of holes flowing into the light emitting layer to control the performance of the entire device.
  • the hole control material a compound having the ability to prevent the inflow of electrons from the light emitting layer to the anode and to control the flow of holes injected to the light emitting layer or the light emitting material is preferable.
  • an arylamine-based organic material may be used as the hole control layer, but is not limited thereto.
  • the organic light emitting device may include one or two or more light emitting layers.
  • the compound represented by Chemical Formula 1 may be used as the light emitting material in one or two or more light emitting layers.
  • the emission layer that does not include the compound represented by Formula 1 may include a light emitting material other than the compound of Formula 1.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples of the light emitting material include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • a host / dopant system may be used as a light emitting material of the light emitting layer.
  • the light emitting layer including the compound represented by Chemical Formula 1 as a dopant may include the compound represented by Chemical Formula H as a host material in the light emitting layer.
  • the light emitting layer other than the light emitting layer including the compound represented by Chemical Formula 1 may include the following host material or dopant material.
  • the host material of the light emitting layer may be a condensed aromatic ring derivative or a hetero ring-containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladders. Type furan compounds, pyrimidine derivatives, and the like, but is not limited thereto.
  • the dopant material of the light emitting layer includes an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, and the like.
  • aromatic amine derivative pyrene, anthracene, chrysene, periplanthene and the like having an arylamine group may be used as a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group.
  • the styrylamine compound a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine may be used.
  • styrylamine compound examples include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like.
  • the metal complex may be an iridium complex, a platinum complex, or the like, but is not limited thereto.
  • the electron control layer is a layer that blocks the flow of holes from the light emitting layer to the cathode and controls the performance of the entire device by adjusting the electrons flowing into the light emitting layer.
  • the electron adjusting material a compound having the ability to prevent the inflow of holes from the light emitting layer to the cathode and to control the electrons injected into the light emitting layer or the light emitting material is preferable.
  • the electron control material an appropriate material may be used according to the configuration of the organic material layer used in the device.
  • the electron control layer is positioned between the light emitting layer and the cathode, preferably provided in direct contact with the light emitting layer.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer.
  • the electron transporting material a material capable of injecting electrons well from a cathode or an electron injection layer and transferring the electrons to a light emitting layer is suitable.
  • the electron transporting material include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired negative electrode material as used in the prior art.
  • the negative electrode material includes a material having a low work function; And aluminum layers or silver layers. Examples of the material having a low work function include cesium, barium, calcium, ytterbium, and samarium, and after forming a layer from the material, an aluminum layer or a silver layer may be formed on the layer.
  • the electron injection layer is a layer for injecting electrons received from the electrode into the light emitting layer.
  • the electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and prevents the movement of excitons generated in the light emitting layer to the hole injection layer, Moreover, it is preferable to use the compound excellent in the thin film formation ability.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
  • the organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
  • a glass substrate (corning 7059 glass) coated with a thin film of ITO at a thickness of 100 nm was placed in distilled water in which a dispersant was dissolved and ultrasonically washed. Fischer Co. was used for the detergent, and Millipore Co. Secondary filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.
  • the following compound HAT-CN was thermally vacuum deposited to a thickness of 5 nm on the prepared ITO transparent electrode to form a hole injection layer.
  • the following compound HT-A was vacuum deposited to form a first hole transport layer having a thickness of 100 nm, and the following compound HT-B was subsequently vacuum deposited to form a second hole transport layer having a thickness of 10 nm.
  • the host compound BH-1 and compound 1 were vacuum deposited on the second hole transport layer at a weight ratio of 98: 2 to form a light emitting layer having a thickness of 20 nm.
  • the deposition rate of the organic material was maintained at 0.1 nm / sec
  • the deposition rate of silver and magnesium was 0.02 nm / sec
  • the deposition rate of aluminum was 0.3 nm / sec to 0.7 nm / sec.
  • the organic light emitting device of Examples 2 to 26 was manufactured by the same method as Example 1, except that the compound of Table 1 was used instead of the compound 1 in Example 1.
  • Example 27 The organic light emitting device of Example 27 was manufactured in the same manner as in Example 1, except that Compound BH-2 was used for Compound 1 instead of Compound BH-1 and Compound 17 was used instead of Compound 1 in Example 1.
  • Example 28 The organic light emitting device of Example 28 was used in Example 1, except that Compound BH-1 and Compound BH-2 were used in the light emitting layer instead of Compound BH-1 in a weight ratio of 1: 1, and Compound 11 was used instead of Compound 1. It produced in the same manner as in Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound of Table 1 in place of Compound 1 in Example 1.
  • T 95 means the time required to reduce the luminance to 95% when the initial luminance at the current density of 20 mA / cm 2 is 100%.
  • the compound represented by Formula 1 according to the present invention can be used in the blue light emitting layer of the organic light emitting device, the organic light emitting device of Examples 1 to 28 including this as a dopant of the light emitting layer

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Abstract

The present specification provides a compound represented by chemical formula 1 and an organic light emitting diode comprising same.

Description

화합물 및 이를 포함하는 유기 발광 소자Compound and organic light emitting device comprising same
본 발명은 화학식 1로 표시되는 화합물 및 이를 포함하는 유기 발광 소자를 제공한다.The present invention provides a compound represented by Formula 1 and an organic light emitting device including the same.
본 출원은 2018년 5월 21일 한국특허청에 제출된 한국 특허 출원 제10-2018-0057812호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the filing date of Korean Patent Application No. 10-2018-0057812 filed with the Korea Intellectual Property Office on May 21, 2018, the entire contents of which are incorporated herein.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어지며, 예컨대 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 난다.In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. In this case, the organic material layer has a multi-layered structure composed of different materials in order to increase efficiency and stability of the organic light emitting device. For example, the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode, electrons are injected into the organic material layer, and excitons are formed when the injected holes and electrons meet. It glows when it falls to the ground.
상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다.There is a continuing need for the development of new materials for such organic light emitting devices.
<선행기술문헌> 한국 공개특허공보 제10-2013-0028673호<Prior art document> Korean Unexamined Patent Publication No. 10-2013-0028673
본 명세서는 화학식 1으로 표시되는 화합물을 포함함으로써, 구동 전압이 낮거나, 발광 효율이 높거나, 수명 특성이 좋거나, 색 순도가 높은 유기 발광 소자를 제공하고자 한다. The present specification is intended to provide an organic light emitting device having a low driving voltage, high luminous efficiency, good lifespan characteristics, or high color purity by including a compound represented by Chemical Formula 1.
본 명세서의 일 실시상태는 하기 화학식 1로 표시되는 것인 화합물을 제공한다.An exemplary embodiment of the present specification provides a compound represented by the following Formula 1.
[화학식 1][Formula 1]
Figure PCTKR2019006050-appb-I000001
Figure PCTKR2019006050-appb-I000001
상기 화학식 1에 있어서,In Chemical Formula 1,
X는 O, S 또는 Si(R1)(R2)이고,X is O, S or Si (R1) (R2),
R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 알킬기 또는 아릴기이며,R1 and R2 are the same as or different from each other, and each independently hydrogen, an alkyl group or an aryl group,
Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 사이클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
상기 '치환 또는 비치환'에서의 치환기는 중수소; 할로겐기; 중수소로 치환 또는 비치환된 사슬형 알킬기; 중수소로 치환 또는 비치환된 사이클로알킬기; 할로알킬기; 알킬기 또는 아릴기로 치환 또는 비치환된 실릴기; 중수소로 치환 또는 비치환된 아릴기; 또는 중수소로 치환 또는 비치환된 헤테로아릴기이며,The substituent in the "substituted or unsubstituted" is deuterium; Halogen group; A chain alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group unsubstituted or substituted with deuterium; Haloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An aryl group unsubstituted or substituted with deuterium; Or a heteroaryl group unsubstituted or substituted with deuterium,
m은 0 또는 1이다.m is 0 or 1;
본 명세서의 일 실시상태는 제1 전극; 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자에 있어서, 상기 유기물층은 전술한 화학식 1로 표시되는 화합물을 포함하는 것인 유기 발광 소자를 제공한다.An exemplary embodiment of the present specification includes a first electrode; Second electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein the organic material layer includes the compound represented by Chemical Formula 1 described above.
본 명세서에 기재된 화합물은 유기 발광 소자의 유기물층의 재료로 사용될 수 있다. 일 실시상태에 있어서, 본 명세서에 기재된 화합물은 정공 주입, 정공 수송, 정공 주입과 정공 수송 또는 발광 재료로 사용될 수 있다. The compound described herein may be used as a material of the organic material layer of the organic light emitting device. In one embodiment, the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport or luminescent materials.
몇몇 실시상태에 있어서, 본 발명의 화합물을 포함하는 유기 발광 소자는 효율이 향상될 수 있다.In some embodiments, the organic light emitting device including the compound of the present invention may be improved in efficiency.
몇몇 실시상태에 있어서, 본 발명의 화합물을 포함하는 유기 발광 소자는 구동전압이 낮아질 수 있다.In some embodiments, the organic light emitting device including the compound of the present invention may have a low driving voltage.
몇몇 실시상태에 있어서, 본 발명의 화합물을 포함하는 유기 발광 소자는 수명 특성이 향상될 수 있다.In some embodiments, the organic light emitting device including the compound of the present invention may have improved lifetime characteristics.
도 1은 기판(1), 양극(2), 유기물층(3) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.FIG. 1 illustrates an example of an organic light emitting device including a substrate 1, an anode 2, an organic material layer 3, and a cathode 4.
도 2는 기판(1), 양극(2), 정공 주입층(5), 정공 수송층(6), 정공 조절층(7), 발광층(8), 전자 수송층(9), 전자 주입층(10) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 2 shows a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a hole control layer 7, a light emitting layer 8, an electron transport layer 9, an electron injection layer 10. And an example of an organic light emitting element composed of a cathode 4.
도 3은 기판(1), 양극(2), 정공 주입층(5), 제1 정공 수송층(6a), 제2 정공 수송층(6b), 발광층(8), 전자 주입 및 수송층(11) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.3 shows a substrate 1, an anode 2, a hole injection layer 5, a first hole transport layer 6a, a second hole transport layer 6b, a light emitting layer 8, an electron injection and transport layer 11, and a cathode. The example of the organic light emitting element which consists of (4) is shown.
<부호의 설명><Description of the code>
1: 기판1: substrate
2: 양극2: anode
3: 유기물층3: organic layer
4: 음극4: cathode
5: 정공 주입층5: hole injection layer
6: 정공 수송층6: hole transport layer
6a: 제1 정공 수송층6a: first hole transport layer
6b: 제2 정공 수송층6b: second hole transport layer
7: 정공 조절층7: hole control layer
8: 발광층8: light emitting layer
9: 전자 수송층9: electron transport layer
10: 전자 주입층10: electron injection layer
11: 전자 주입 및 수송층11: electron injection and transport layer
이하 본 발명을 더욱 상세히 설명한다.Hereinafter, the present invention will be described in more detail.
상기 치환기들의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Examples of the substituents are described below, but are not limited thereto.
본 명세서에 있어서,
Figure PCTKR2019006050-appb-I000002
는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In the present specification,
Figure PCTKR2019006050-appb-I000002
Means a site which is bonded to another substituent or binding moiety.
상기 "치환"이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미한다. 상기 치환기가 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않는다. 상기 치환기가 2 이상인 경우, 2 이상의 치환기는 서로 동일하거나 상이할 수 있다.The term "substituted" means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent. The position at which the substituent is substituted is not limited as long as the position at which the hydrogen atom is substituted, that is, the position at which the substituent is substituted. When the substituents are two or more, two or more substituents may be the same or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 알킬기; 알킬기 또는 아릴기로 치환 또는 비치환된 실릴기; 알킬기 또는 아릴기로 치환 또는 비치환된 포스핀옥사이드기; 아릴기; 및 헤테로아릴기로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나, 상기 예시된 치환기 중 2개의 치환기가 연결된 기로 치환 또는 비치환된 것을 의미한다. As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; An alkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Phosphine oxide groups unsubstituted or substituted with alkyl or aryl groups; Aryl group; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of a heteroaryl group, or substituted or unsubstituted with a group to which two substituents of the substituents exemplified above.
본 명세서에 있어서, A 또는 B로 치환된다는 의미는, 1 또는 2 이상의 A로 치환되거나, 1 또는 2 이상의 B로 치환되거나, 1 또는 2 이상의 A와 1 또는 2 이상의 B로 함께 치환되는 것을 모두 포함한다.In the present specification, the meaning of being substituted with A or B includes all substituted with 1 or 2 or more A, substituted with 1 or 2 or more B, or substituted together with 1 or 2 or more A and 1 or 2 or more B. do.
본 명세서에 있어서, 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine.
본 명세서에 있어서, 실릴기는 -SiH3이고, 상기 실릴기는 알킬기 또는 아릴기로 치환 또는 비치환될 수 있다. 상기 알킬기 또는 아릴기로 치환 또는 비치환된 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나, 이에 한정되지 않는다.In the present specification, the silyl group is -SiH 3 , and the silyl group may be substituted or unsubstituted with an alkyl group or an aryl group. The silyl group unsubstituted or substituted with the alkyl group or the aryl group is specifically trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, Phenylsilyl group and the like, but is not limited thereto.
본 명세서에 있어서, 알킬실릴기는 알킬기로 치환된 실릴기를 의미하며, 아릴실릴기는 아릴기로 치환된 실릴기를 의미한다.In the present specification, the alkylsilyl group means a silyl group substituted with an alkyl group, and the arylsilyl group means a silyl group substituted with an aryl group.
본 명세서에 있어서, 알킬실릴기 중의 알킬기에는 하기 알킬기에 관한 설명이 적용될 수 있다.In the present specification, the description about the following alkyl group may be applied to the alkyl group in the alkylsilyl group.
본 명세서에 있어서, 아릴실릴기 중의 아릴기에는 하기 아릴기에 관한 설명이 적용될 수 있다.In the present specification, the description of the following aryl group may be applied to the aryl group in the arylsilyl group.
본 명세서에 있어서, 알킬기는 직쇄 또는 분지쇄의 포화 탄화수소를 의미한다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 6이다. 상기 알킬기는 사슬형 또는 고리형일 수 있다. In the present specification, an alkyl group means a straight or branched chain saturated hydrocarbon. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. The alkyl group may be chain or cyclic.
상기 사슬형 알킬기의 구체적인 예로는 메틸, 에틸, 프로필, n-프로필, 이소프로필, 부틸, n-부틸, 이소부틸, tert-부틸, sec-부틸, 1-메틸부틸, 1-에틸부틸, 펜틸, n-펜틸, 이소펜틸, 네오펜틸, n-헥실, 1-메틸펜틸, 2-메틸펜틸, 4-메틸펜틸, 3,3-디메틸부틸, 2-에틸부틸, n-헵틸, n-옥틸, tert-옥틸, 1-메틸헵틸, 2-에틸헥실, 2-프로필펜틸, n-노닐, 2,2-디메틸헵틸, 1-에틸프로필, 1,1-디메틸프로필, 이소헥실, 4-메틸헥실, 5-메틸헥실 등이 있으나, 이에 한정되지 않는다.Specific examples of the chain alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, n-octyl, tert -Octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 4-methylhexyl, 5 Methylhexyl, and the like, but is not limited thereto.
상기 고리형 알킬기(사이클로알킬기)의 탄소수는 특별히 한정되지 않으나 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 14이다. 또 하나의 실시상태에 따르면, 상기 사이클로알킬기의 탄소수는 3 내지 8이다. 상기 사이클로알킬기의 구체적인 예로는 사이클로프로필, 사이클로부틸, 사이클로펜틸, 사이클로헵틸, 사이클로옥틸 등이 있으나, 이에 한정되지 않는다. Carbon number of the cyclic alkyl group (cycloalkyl group) is not particularly limited, but according to one embodiment, the carbon number of the cycloalkyl group is 3 to 14. According to another exemplary embodiment, the cycloalkyl group has 3 to 8 carbon atoms. Specific examples of the cycloalkyl group include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclooctyl, and the like.
본 명세서에 있어서, 아릴기는 전체적으로 또는 부분적으로 불포화된 치환 또는 비치환된 모노사이클릭 또는 폴리사이클릭을 의미한다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 상기 아릴기는 단환식 아릴기 또는 다환식 아릴기일 수 있다. 상기 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 있으나, 이에 한정되지 않는다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트레닐기, 페릴레닐기, 플루오란테닐기, 트리페닐레닐기, 페날레닐기, 파이레닐기, 테트라세닐기, 크라이세닐기, 펜타세닐기, 플루오레닐기, 인데닐기, 아세나프틸기, 벤조플루오레닐기, 스피로바이플루오레닐기 등이 있으나, 이에 한정되지 않는다.In the present specification, an aryl group means a substituted or unsubstituted monocyclic or polycyclic which is wholly or partially unsaturated. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. The aryl group may be a monocyclic aryl group or a polycyclic aryl group. Examples of the monocyclic aryl group include a phenyl group, a biphenyl group, and a terphenyl group, but are not limited thereto. As said polycyclic aryl group, a naphthyl group, anthracenyl group, a phenanthrenyl group, a perrylenyl group, a fluoranthenyl group, a triphenylenyl group, a penalenyl group, a pyrenyl group, a tetrasenyl group, a chrysenyl group, a pentaxenyl group , Fluorenyl group, indenyl group, acenaphthyl group, benzofluorenyl group, spirobifluorenyl group and the like, but is not limited thereto.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
상기 치환된 플루오레닐기로는 As the substituted fluorenyl group
Figure PCTKR2019006050-appb-I000003
등이 있으나, 이에 한정되지 않는다.
Figure PCTKR2019006050-appb-I000003
Etc., but is not limited thereto.
본 명세서에 있어서, 헤테로아릴기는 이종원자로 N, O 및 S 중 1개 이상을 포함하는 고리기로서, 탄소수는 특별히 한정되지 않으나 2 내지 40이다. 다른 실시상태에 따르면, 상기 헤테로아릴기의 탄소수는 2 내지 30이다. 헤테로아릴기의 예로는 티오페닐기, 퓨라닐기, 피롤릴기, 이미다졸릴기, 티아졸릴기, 옥사졸릴기, 옥사디아졸릴기, 피리디닐기, 비피리디닐기, 피리미디닐기, 트리아지닐기, 트리아졸릴기, 아크리디닐기, 카르볼리닐기, 아세나프토퀴녹살리닐기, 인데노퀴나졸리닐기, 인데노이소퀴놀리닐기, 인데노퀴놀리닐기, 피리도인돌릴기, 피리다지닐기, 피라지닐기, 퀴놀리닐기, 퀴나졸리닐기, 퀴녹살리닐기, 프탈라지닐기, 피리도피리미디닐기, 피리도피라지닐기, 피라지노피라지닐기, 이소퀴놀리닐기, 인돌릴기, 카바졸릴기, 벤즈옥사졸릴기, 벤즈이미다졸릴기, 벤조티아졸릴기, 벤조카바졸릴기, 벤조티오페닐기, 디벤조티오페닐기, 벤조퓨라닐기, 디벤조퓨라닐기, 페난쓰롤리닐기(phenanthrolinyl), 이소옥사졸릴기, 티아디아졸릴기, 페녹사지닐기, 페노티아지닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heteroaryl group is a ring group containing one or more of N, O and S as heteroatoms, and carbon number is not particularly limited, but is 2 to 40. According to another exemplary embodiment, the heteroaryl group has 2 to 30 carbon atoms. Examples of the heteroaryl group are thiophenyl group, furanyl group, pyrrolyl group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridinyl group, bipyridinyl group, pyrimidinyl group, triazinyl group, tria Sleepyl group, acridinyl group, carbolinyl group, acenaphthoquinoxalinyl group, indenoquinazolinyl group, indenoisoquinolinyl group, indenoquinolinyl group, pyridoindolyl group, pyridazinyl group, pyrazinyl group, Quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl Group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl group, benzofuranyl group, dibenzofuranyl group, phenanthrolinyl group (phenanthrolinyl), isoxazolyl group, thia Diazolyl group, phenoxazinyl group, phenothiazinyl Although the like, but are not limited thereto.
본 명세서의 일 실시상태는 상기 화학식 1로 표시되는 화합물을 제공한다.An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1.
본 발명 화합물은 나프토[2,3-b]벤조퓨란의 벤젠 고리에 벤조퓨란, 벤조티오펜, 벤조실롤, 나프토퓨란, 나프토티오펜 또는 나프토실롤이 축합된 구조를 코어 구조로 가진다. 상기 코어 구조로 인하여 화합물의 LUMO 에너지 준위가 낮아지므로, 본 발명 화합물을 발광층의 도판트 물질로 사용하는 경우, 발광층의 호스트 물질로부터 본 발명 화합물으로의 에너지 전이(energy transfer)가 용이하다.The compound of the present invention has a structure in which benzofuran, benzothiophene, benzosilol, naphthofuran, naphthothiophene or naphthosilol is condensed in a benzene ring of naphtho [2,3-b] benzofuran as a core structure. Since the LUMO energy level of the compound is lowered due to the core structure, when the compound of the present invention is used as a dopant material of the light emitting layer, energy transfer from the host material of the light emitting layer to the compound of the present invention is easy.
또한 본 발명 화합물의 코어구조로 인하여 HOMO 에너지 준위와 LUMO 에너지 준위의 겹침(overlap)이 증가하여, 복사 전이 확률(Oscillator strength)을 증가시켜 소자의 발광 효율을 높일 수 있다.In addition, the overlap of the HOMO energy level and the LUMO energy level is increased due to the core structure of the compound of the present invention, and thus the emission efficiency of the device can be improved by increasing the radiation transfer probability.
화학식 1의 화합물은 2개의 아민기를 포함함으로써, 아민기를 포함하지 않거나 1개의 아민기를 포함하는 구조에 비하여 복사 전이 확률(Oscillator strength)이 증가되어 소자의 발광 효율이 높다.Since the compound of Formula 1 includes two amine groups, the radiation transition probability (Oscillator strength) is increased compared to the structure containing no amine group or one amine group, thereby increasing the luminous efficiency of the device.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 탄소수 1 내지 10의 알킬기 또는 탄소수 6 내지 24의 아릴기이다.In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 24 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 탄소수 1 내지 6의 알킬기 또는 탄소수 6 내지 18의 아릴기이다.In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 18 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 탄소수 1 내지 4의 알킬기 또는 탄소수 6 내지 12의 아릴기이다.In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, an alkyl group having 1 to 4 carbon atoms, or an aryl group having 6 to 12 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 메틸기 또는 페닐기이다.In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, a methyl group, or a phenyl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2 중 적어도 어느 하나는 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.In one embodiment of the present specification, at least one of Ar1 and Ar2 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 및 Ar2 중 적어도 어느 하나는 치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.In one embodiment of the present specification, at least one of Ar1 and Ar2 is a substituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar3 및 Ar4 중 적어도 어느 하나는 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.In one embodiment of the present specification, at least one of Ar3 and Ar4 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar3 및 Ar4 중 적어도 어느 하나는 치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.In one embodiment of the present specification, at least one of Ar3 and Ar4 is a substituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 1 또는 2 이상의 치환기로 치환 또는 비치환된 사이클로알킬기; 1 또는 2 이상의 치환기로 치환 또는 비치환된 아릴기; 또는 1 또는 2 이상의 치환기로 치환 또는 비치환된 헤테로아릴기이며, 상기 '치환 또는 비치환'에서의 치환기는 중수소; 할로겐기; 중수소로 치환 또는 비치환된 사슬형 알킬기; 중수소로 치환 또는 비치환된 사이클로알킬기; 할로알킬기; 알킬기 또는 아릴기로 치환 또는 비치환된 실릴기; 중수소로 치환 또는 비치환된 아릴기; 또는 중수소로 치환 또는 비치환된 헤테로아릴기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a cycloalkyl group unsubstituted or substituted with one or two or more substituents; An aryl group unsubstituted or substituted with one or two or more substituents; Or a heteroaryl group unsubstituted or substituted with one or two or more substituents, and the substituent in 'substituted or unsubstituted' is deuterium; Halogen group; A chain alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group unsubstituted or substituted with deuterium; Haloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An aryl group unsubstituted or substituted with deuterium; Or a heteroaryl group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 3 내지 8의 사이클로알킬기; 치환 또는 비치환된 탄소수 6 내지 25의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 24의 헤테로아릴기이며, 상기 '치환 또는 비치환'에서의 치환기는 중수소; 할로겐기; 중수소로 치환 또는 비치환된 사슬형 알킬기; 중수소로 치환 또는 비치환된 사이클로알킬기; 할로알킬기; 알킬기 또는 아릴기로 치환 또는 비치환된 실릴기; 중수소로 치환 또는 비치환된 아릴기; 또는 중수소로 치환 또는 비치환된 헤테로아릴기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms; Substituted or unsubstituted aryl group having 6 to 25 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 24 carbon atoms, the substituent in the "substituted or unsubstituted" is deuterium; Halogen group; A chain alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group unsubstituted or substituted with deuterium; Haloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An aryl group unsubstituted or substituted with deuterium; Or a heteroaryl group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 3 내지 6의 사이클로알킬기; 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 20의 헤테로아릴기이며, 상기 '치환 또는 비치환'에서의 치환기는 중수소; 할로겐기; 중수소로 치환 또는 비치환된 사슬형 알킬기; 중수소로 치환 또는 비치환된 사이클로알킬기; 할로알킬기; 알킬기 또는 아릴기로 치환 또는 비치환된 실릴기; 중수소로 치환 또는 비치환된 아릴기; 또는 중수소로 치환 또는 비치환된 헤테로아릴기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms; Substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms, the substituent in the "substituted or unsubstituted" is deuterium; Halogen group; A chain alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group unsubstituted or substituted with deuterium; Haloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An aryl group unsubstituted or substituted with deuterium; Or a heteroaryl group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 3 내지 6의 사이클로알킬기; 치환 또는 비치환된 탄소수 6 내지 15의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 16의 헤테로아릴기이며, 상기 '치환 또는 비치환'에서의 치환기는 중수소; 할로겐기; 중수소로 치환 또는 비치환된 사슬형 알킬기; 중수소로 치환 또는 비치환된 사이클로알킬기; 할로알킬기; 알킬기 또는 아릴기로 치환 또는 비치환된 실릴기; 중수소로 치환 또는 비치환된 아릴기; 또는 중수소로 치환 또는 비치환된 헤테로아릴기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group having 3 to 6 carbon atoms; Substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 16 carbon atoms, the substituent in the "substituted or unsubstituted" is deuterium; Halogen group; A chain alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group unsubstituted or substituted with deuterium; Haloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An aryl group unsubstituted or substituted with deuterium; Or a heteroaryl group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 사이클로알킬기; 치환 또는 비치환된 1환 내지 4환의 아릴기; 또는 치환 또는 비치환된 1환 내지 5환의 헤테로아릴기이며, 상기 '치환 또는 비치환'에서의 치환기는 중수소; 할로겐기; 중수소로 치환 또는 비치환된 사슬형 알킬기; 중수소로 치환 또는 비치환된 사이클로알킬기; 할로알킬기; 알킬기 또는 아릴기로 치환 또는 비치환된 실릴기; 중수소로 치환 또는 비치환된 아릴기; 또는 중수소로 치환 또는 비치환된 헤테로아릴기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted 1 to 4 ring aryl group; Or a substituted or unsubstituted 1 to 5 ring heteroaryl group, the substituent in the "substituted or unsubstituted" is deuterium; Halogen group; A chain alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group unsubstituted or substituted with deuterium; Haloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An aryl group unsubstituted or substituted with deuterium; Or a heteroaryl group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 사이클로알킬기; 치환 또는 비치환된 1환 내지 3환의 아릴기; 또는 치환 또는 비치환된 1환 내지 4환의 헤테로아릴기이며, 상기 '치환 또는 비치환'에서의 치환기는 중수소; 할로겐기; 중수소로 치환 또는 비치환된 사슬형 알킬기; 중수소로 치환 또는 비치환된 사이클로알킬기; 할로알킬기; 알킬기 또는 아릴기로 치환 또는 비치환된 실릴기; 중수소로 치환 또는 비치환된 아릴기; 또는 중수소로 치환 또는 비치환된 헤테로아릴기이다. In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted 1 to 3 ring aryl group; Or a substituted or unsubstituted 1 to 4 ring heteroaryl group, the substituent in the "substituted or unsubstituted" is deuterium; Halogen group; A chain alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group unsubstituted or substituted with deuterium; Haloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An aryl group unsubstituted or substituted with deuterium; Or a heteroaryl group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 사이클로헥실기; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 티오페닐기; 치환 또는 비치환된 디벤조퓨라닐기; 치환 또는 비치환된 디벤조티오페닐기; 치환 또는 비치환된 카바졸릴기; 치환 또는 비치환된 나프토벤조퓨라닐기; 치환 또는 비치환된 나프토벤조티오페닐기; 치환 또는 비치환된 피리디닐기; 또는 치환 또는 비치환된 퀴놀리닐기이며, 상기 '치환 또는 비치환'에서의 치환기는 중수소; 할로겐기; 중수소로 치환 또는 비치환된 사슬형 알킬기; 중수소로 치환 또는 비치환된 사이클로알킬기; 할로알킬기; 알킬기 또는 아릴기로 치환 또는 비치환된 실릴기; 중수소로 치환 또는 비치환된 아릴기; 또는 중수소로 치환 또는 비치환된 헤테로아릴기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted cyclohexyl group; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted thiophenyl group; Substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophenyl group; Substituted or unsubstituted carbazolyl group; A substituted or unsubstituted naphthobenzofuranyl group; A substituted or unsubstituted naphthobenzothiophenyl group; Substituted or unsubstituted pyridinyl group; Or a substituted or unsubstituted quinolinyl group, the substituent in the 'substituted or unsubstituted' is deuterium; Halogen group; A chain alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group unsubstituted or substituted with deuterium; Haloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An aryl group unsubstituted or substituted with deuterium; Or a heteroaryl group unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 사이클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며, 상기 '치환 또는 비치환'에서의 치환기는 중수소; 할로겐기; 중수소로 치환 또는 비치환된 탄소수 1 내지 6의 사슬형 알킬기; 중수소로 치환 또는 비치환된 탄소수 3 내지 8의 사이클로알킬기; 탄소수 1 내지 6의 할로알킬기; 탄소수 1 내지 6의 알킬기 또는 탄소수 6 내지 15의 아릴기로 치환 또는 비치환된 실릴기; 중수소로 치환 또는 비치환된 탄소수 6 내지 25의 아릴기; 또는 중수소로 치환 또는 비치환된 탄소수 2 내지 24의 헤테로아릴기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, the substituent in the "substituted or unsubstituted" is deuterium; Halogen group; C1-C6 linear alkyl group unsubstituted or substituted by deuterium; A cycloalkyl group having 3 to 8 carbon atoms unsubstituted or substituted with deuterium; Haloalkyl groups having 1 to 6 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 15 carbon atoms; An aryl group having 6 to 25 carbon atoms unsubstituted or substituted with deuterium; Or a heteroaryl group having 2 to 24 carbon atoms unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 사이클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며, 상기 '치환 또는 비치환'에서의 치환기는 중수소; 할로겐기; 중수소로 치환 또는 비치환된 탄소수 1 내지 6의 사슬형 알킬기; 중수소로 치환 또는 비치환된 탄소수 3 내지 6의 사이클로알킬기; 탄소수 1 내지 4의 할로알킬기; 탄소수 1 내지 4의 알킬기 또는 탄소수 6 내지 13의 아릴기로 치환 또는 비치환된 실릴기; 중수소로 치환 또는 비치환된 탄소수 6 내지 13의 아릴기; 또는 중수소로 치환 또는 비치환된 탄소수 2 내지 12의 헤테로아릴기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, the substituent in the "substituted or unsubstituted" is deuterium; Halogen group; C1-C6 linear alkyl group unsubstituted or substituted by deuterium; A cycloalkyl group having 3 to 6 carbon atoms unsubstituted or substituted with deuterium; Haloalkyl groups having 1 to 4 carbon atoms; A silyl group unsubstituted or substituted with an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 13 carbon atoms; An aryl group having 6 to 13 carbon atoms unsubstituted or substituted with deuterium; Or a heteroaryl group having 2 to 12 carbon atoms unsubstituted or substituted with deuterium.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 사이클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며, 상기 '치환 또는 비치환'에서의 치환기는 중수소; 플루오로기; 중수소로 치환 또는 비치환된 메틸기; t-부틸기; 트리플루오로메틸기; 트리메틸실릴기; 중수소로 치환 또는 비치환된 페닐기; 또는 나프틸기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and are each independently a substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group, the substituent in the "substituted or unsubstituted" is deuterium; Fluoro groups; Methyl group unsubstituted or substituted with deuterium; t-butyl group; Trifluoromethyl group; Trimethylsilyl group; A phenyl group unsubstituted or substituted with deuterium; Or a naphthyl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 시클로헥실기; 중수소, 플루오로기, 중수소로 치환 또는 비치환된 메틸기, t-부틸기, 트리플루오로메틸기, 트리메틸실릴기, 페닐기 또는 나프틸기로 치환 또는 비치환된 페닐기; 바이페닐기; 나프틸기; 9,9-디메틸플루오레닐기; 페난트레닐기; 페닐기로 치환 또는 비치환된 티오페닐기; t-부틸기로 치환 또는 비치환된 디벤조퓨라닐기; 디벤조티오페닐기; 메틸기, 페닐기, 또는 중수소로 치환 또는 비치환된 페닐기로 치환 또는 비치환된 카바졸릴기; 나프토벤조퓨라닐기; 나프토벤조티오페닐기; 피리디닐기; 또는 퀴놀리닐기이다.In one embodiment of the present specification, Ar1 to Ar4 are the same as or different from each other, and each independently a cyclohexyl group; Deuterium, fluoro group, phenyl group unsubstituted or substituted with methyl, t-butyl, trifluoromethyl, trimethylsilyl, phenyl or naphthyl groups unsubstituted or substituted with deuterium; Biphenyl group; Naphthyl group; 9,9-dimethyl fluorenyl group; Phenanthrenyl group; Thiophenyl group unsubstituted or substituted with a phenyl group; dibenzofuranyl group unsubstituted or substituted with a t-butyl group; Dibenzothiophenyl group; A carbazolyl group unsubstituted or substituted with a phenyl group unsubstituted or substituted with a methyl group, a phenyl group, or deuterium; Naphthobenzofuranyl group; Naphthobenzothiophenyl group; Pyridinyl group; Or a quinolinyl group.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 1-1 내지 화학식 1-3 중 어느 하나로 표시된다.In one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3.
[화학식 1-1][Formula 1-1]
Figure PCTKR2019006050-appb-I000004
Figure PCTKR2019006050-appb-I000004
[화학식 1-2][Formula 1-2]
Figure PCTKR2019006050-appb-I000005
Figure PCTKR2019006050-appb-I000005
[화학식 1-3][Formula 1-3]
Figure PCTKR2019006050-appb-I000006
Figure PCTKR2019006050-appb-I000006
상기 화학식 1-1 내지 화학식 1-3에 있어서,In Chemical Formulas 1-1 to 1-3,
X1 및 X2 중 어느 하나는 직접결합이고, 나머지 하나는 X이며,One of X1 and X2 is a direct bond, the other is X,
X, Ar1 내지 Ar4 및 m의 정의는 화학식 1에서 정의한 바와 동일하다.The definitions of X, Ar1 to Ar4 and m are the same as defined in the formula (1).
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 2-1 내지 화학식 2-4 중 어느 하나로 표시된다.In one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1 to 2-4.
[화학식 2-1][Formula 2-1]
Figure PCTKR2019006050-appb-I000007
Figure PCTKR2019006050-appb-I000007
[화학식 2-2][Formula 2-2]
Figure PCTKR2019006050-appb-I000008
Figure PCTKR2019006050-appb-I000008
[화학식 2-3][Formula 2-3]
Figure PCTKR2019006050-appb-I000009
Figure PCTKR2019006050-appb-I000009
[화학식 2-4][Formula 2-4]
Figure PCTKR2019006050-appb-I000010
Figure PCTKR2019006050-appb-I000010
상기 화학식 2-1 내지 화학식 2-4에 있어서,In Chemical Formulas 2-1 to 2-4,
X 및 Ar1 내지 Ar4의 정의는 화학식 1에서 정의한 바와 동일하다.The definitions of X and Ar1 to Ar4 are the same as defined in the formula (1).
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 3-1 내지 화학식 3-4 중 어느 하나로 표시된다.In one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 3-1 to 3-4.
[화학식 3-1][Formula 3-1]
Figure PCTKR2019006050-appb-I000011
Figure PCTKR2019006050-appb-I000011
[화학식 3-2][Formula 3-2]
Figure PCTKR2019006050-appb-I000012
Figure PCTKR2019006050-appb-I000012
[화학식 3-3][Formula 3-3]
Figure PCTKR2019006050-appb-I000013
Figure PCTKR2019006050-appb-I000013
[화학식 3-4][Formula 3-4]
Figure PCTKR2019006050-appb-I000014
Figure PCTKR2019006050-appb-I000014
상기 화학식 3-1 내지 화학식 3-4에 있어서,In Chemical Formulas 3-1 to 3-4,
X, Ar1 내지 Ar4 및 m의 정의는 화학식 1에서 정의한 바와 동일하다.The definitions of X, Ar1 to Ar4 and m are the same as defined in the formula (1).
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 4-1 내지 화학식 4-6 중 어느 하나로 표시된다.In one embodiment of the present specification, Chemical Formula 1 is represented by any one of the following Chemical Formulas 4-1 to 4-6.
[화학식 4-1][Formula 4-1]
Figure PCTKR2019006050-appb-I000015
Figure PCTKR2019006050-appb-I000015
[화학식 4-2][Formula 4-2]
Figure PCTKR2019006050-appb-I000016
Figure PCTKR2019006050-appb-I000016
[화학식 4-3][Formula 4-3]
Figure PCTKR2019006050-appb-I000017
Figure PCTKR2019006050-appb-I000017
[화학식 4-4][Formula 4-4]
Figure PCTKR2019006050-appb-I000018
Figure PCTKR2019006050-appb-I000018
[화학식 4-5][Formula 4-5]
Figure PCTKR2019006050-appb-I000019
Figure PCTKR2019006050-appb-I000019
[화학식 4-6][Formula 4-6]
Figure PCTKR2019006050-appb-I000020
Figure PCTKR2019006050-appb-I000020
상기 화학식 4-1 내지 화학식 4-6에 있어서,In Chemical Formulas 4-1 to 4-6,
X, Ar1 내지 Ar4 및 m의 정의는 화학식 1에서 정의한 바와 동일하다.The definitions of X, Ar1 to Ar4 and m are the same as defined in the formula (1).
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화합물들 중에서 선택된 어느 하나이다.In one embodiment of the present specification, the compound represented by Formula 1 is any one selected from the following compounds.
Figure PCTKR2019006050-appb-I000021
Figure PCTKR2019006050-appb-I000021
Figure PCTKR2019006050-appb-I000022
Figure PCTKR2019006050-appb-I000022
Figure PCTKR2019006050-appb-I000023
Figure PCTKR2019006050-appb-I000023
Figure PCTKR2019006050-appb-I000024
Figure PCTKR2019006050-appb-I000024
Figure PCTKR2019006050-appb-I000025
Figure PCTKR2019006050-appb-I000025
Figure PCTKR2019006050-appb-I000026
Figure PCTKR2019006050-appb-I000026
본 명세서에 따른 화학식 1으로 표시되는 화합물은 하기 일반식 1의 방법에 따라 제조될 수 있다.The compound represented by Formula 1 according to the present specification may be prepared according to the method of the following Formula 1.
[일반식 1][Formula 1]
Figure PCTKR2019006050-appb-I000027
Figure PCTKR2019006050-appb-I000027
상기 일반식 1에 있어서, X, Ar1 내지 Ar4 및 m의 정의는 화학식 1에서 정의한 바와 동일하고, R은 유기기이다.In the general formula 1, X, Ar1 to Ar4 and m are the same as defined in the formula (1), R is an organic group.
상기 일반식 1은 화학식 1로 표시되는 화합물을 형성하는 방법의 하나의 예시로서, 화학식 1로 표시되는 화합물의 합성 방법은 상기 일반식 1에 한정되지 않으며, 당 기술분야에 알려져 있는 방법에 의할 수 있다. Formula 1 is an example of a method of forming a compound represented by Formula 1, and the synthesis method of the compound represented by Formula 1 is not limited to the above Formula 1, by a method known in the art Can be.
본 명세서는 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다.The present specification provides an organic light emitting device including the compound represented by Chemical Formula 1.
본 명세서의 일 실시상태는, 제1 전극, 제2 전극 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층은 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 발광 소자를 제공한다.An exemplary embodiment of the present specification provides an organic light emitting device including a first electrode, a second electrode, and one or more organic material layers provided between the first electrode and the second electrode, wherein the organic material layer is represented by Chemical Formula 1 It provides an organic light emitting device comprising a compound.
본 명세서의 일 실시상태는, 제1 전극, 제2 전극 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 발광 소자를 제공한다.An exemplary embodiment of the present specification provides an organic light emitting device including a first electrode, a second electrode, and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers is the chemical formula It provides an organic light emitting device comprising the compound represented by 1.
본 명세서의 일 실시상태는, 제1 전극, 제2 전극 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 1층 이상의 유기물층 중 어느 하나의 층은 상기 화학식 1로 표시되는 화합물은 포함하는 것인 유기 발광 소자를 제공한다.An exemplary embodiment of the present specification is an organic light emitting device including a first electrode, a second electrode, and at least one organic material layer provided between the first electrode and the second electrode, wherein any one of the at least one organic material layer is provided. The layer provides an organic light emitting device comprising the compound represented by Formula 1.
본 명세서의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기 발광 소자는 유기물층으로서 정공 주입층, 정공 수송층, 정공 수송과 주입을 동시에 하는 층, 정공 조절층, 발광층, 전자 조절층, 전자 수송층, 전자 주입층, 전자 주입과 수송을 동시에 하는 층 등을 포함할 수 있다.The organic material layer of the organic light emitting device of the present specification may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may be a hole injection layer, a hole transport layer, a layer for simultaneously transporting and injecting holes, a hole control layer, a light emitting layer, an electron control layer, an electron transport layer, an electron injection layer, an electron injection and transport as an organic material layer It may include a layer or the like.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 정공 수송층, 정공 주입층, 정공 주입과 수송을 동시에 하는 층 또는 정공 조절층을 포함하고, 상기 정공 수송층, 정공 주입층, 정공 주입과 수송을 동시에 하는 층 또는 정공 조절층은 상기 화학식 1로 표시되는 화합물을 포함한다. 이는 정공 수송층, 정공 주입층, 정공 주입과 수송을 동시에 하는 층 및 정공 조절층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함한다는 것을 의미한다. In one embodiment of the present specification, the organic material layer includes a hole transport layer, a hole injection layer, a layer for simultaneously injecting and transporting holes or a hole control layer, and simultaneously performing the hole transporting layer, the hole injection layer, and the hole injection and transporting. The layer or the hole control layer includes a compound represented by Chemical Formula 1. This means that at least one of the hole transport layer, the hole injection layer, the layer for simultaneously injecting and transporting the hole, and the hole control layer includes the compound represented by Chemical Formula 1.
본 명세서에 있어서, 전자 주입 및 수송층은 전자 주입과 수송을 동시에 하는 층이며, 정공 주입 및 수송층은 정공 주입과 수송을 동시에 하는 층이다.In the present specification, the electron injection and transport layer is a layer that simultaneously performs electron injection and transport, and the hole injection and transport layer is a layer that simultaneously performs hole injection and transport.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함한다.In one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 2층 이상의 발광층을 포함할 수 있고, 그 중 어느 하나의 발광층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In one embodiment of the present specification, the organic light emitting device may include two or more light emitting layers, and any one of the light emitting layers may include a compound represented by Chemical Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 2층 이상의 발광층을 포함할 수 있고, 그 중 2층 이상의 층은 각각 독립적으로 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.In an exemplary embodiment of the present specification, the organic light emitting device may include two or more light emitting layers, and two or more layers may each independently include a compound represented by Chemical Formula 1.
본 명세서의 일 실시상태에 있어서, 2층 이상의 발광층은 수직으로 또는 수평으로 구비될 수 있다.In one embodiment of the present specification, two or more light emitting layers may be provided vertically or horizontally.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물이 여러 유기물층에 포함된다고 할 때, 각각의 유기물층에 포함되는 화학식 1로 표시되는 화합물은 서로 동일하거나 상이할 수 있다.In an exemplary embodiment of the present specification, when the compound represented by Formula 1 is included in several organic material layers, the compound represented by Formula 1 included in each organic material layer may be the same or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 복수의 발광층을 포함할 수 있고, 각각의 발광층은 동일한 색을 띠거나 서로 상이한 색을 띨 수 있다.In one embodiment of the present specification, the organic light emitting device may include a plurality of light emitting layers, and each light emitting layer may have the same color or may have a different color from each other.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물을 포함하는 발광층은 청색 발광층이다.In one embodiment of the present specification, the light emitting layer including the compound represented by Formula 1 is a blue light emitting layer.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 상기 화학식 1로 표시되는 화합물을 포함하는 1층의 발광층을 포함하는 청색의 유기 발광 소자이다.In one embodiment of the present specification, the organic light emitting diode is a blue organic light emitting diode including one light emitting layer including the compound represented by Chemical Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 상기 화학식 1로 표시되는 화합물을 포함하는 청색의 발광층 이외에도 적색 또는 녹색을 띠는 복수의 발광층을 더 포함할 수 있으며, 이 경우 백색의 유기 발광 소자 또한 구현될 수 있다.In an exemplary embodiment of the present specification, the organic light emitting diode may further include a plurality of light emitting layers of red or green color in addition to the blue light emitting layer including the compound represented by Chemical Formula 1, in which case the organic light emitting white light is emitted. The device may also be implemented.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물은 발광층에 도판트로서 포함된다.In one embodiment of the present specification, the compound represented by Chemical Formula 1 is included as a dopant in the emission layer.
본 명세서의 일 실시상태에 있어서, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함하고, 상기 발광층은 하기 화학식 H로 표시되는 화합물을 더 포함한다.In one embodiment of the present specification, the light emitting layer includes a compound represented by Chemical Formula 1, and the light emitting layer further includes a compound represented by Chemical Formula H.
[화학식 H][Formula H]
Figure PCTKR2019006050-appb-I000028
Figure PCTKR2019006050-appb-I000028
상기 화학식 H에 있어서,In Chemical Formula H,
L1 및 L2는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며,L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar5 및 Ar6는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R3는 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 치환 또는 비치환된 사슬형 알킬기; 치환 또는 비치환된 사이클로알킬기; 알킬기 또는 아릴기로 치환 또는 비치환된 실릴기; 알킬기 또는 아릴기로 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,R3 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted chain alkyl group; A substituted or unsubstituted cycloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Phosphine oxide groups unsubstituted or substituted with alkyl or aryl groups; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
a는 0 내지 8의 정수이고, a가 2 이상인 경우 복수의 R3는 서로 동일하거나 상이하다.a is an integer of 0-8, and when a is 2 or more, some R <3> is the same or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 발광층은 상기 화학식 1로 표시되는 화합물; 및 상기 화학식 H로 표시되는 화합물의 1종 또는 2종 이상을 포함한다.In one embodiment of the present specification, the light emitting layer is a compound represented by Chemical Formula 1; And one or two or more of the compounds represented by the above formula (H).
본 명세서의 일 실시상태에 있어서, 상기 발광층이 2종 이상의 상기 화학식 H로 표시되는 화합물을 포함한다고 할 때, 상기 화학식 H로 표시되는 복수의 화합물은 서로 동일하거나 상이할 수 있다.In an exemplary embodiment of the present specification, when the light emitting layer includes two or more compounds represented by Formula (H), a plurality of compounds represented by Formula (H) may be the same as or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 또는 탄소수 6 내지 16의 아릴렌기이다.In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 16 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 또는 탄소수 6 내지 12의 아릴렌기이다.In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 12 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 또는 1환 내지 3환의 아릴렌기이다.In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 1 to 3 rings.
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 또는 1환 또는 2환의 아릴렌기이다.In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; Or a monocyclic or bicyclic arylene group.
본 명세서의 일 실시상태에 있어서, 상기 L1 및 L2는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 또는 나프틸렌기이다.In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently a direct bond; Phenylene group; Or a naphthylene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar5 및 Ar6는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 24의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 26의 헤테로아릴기이다.In one embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 26 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Ar5 및 Ar6는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 20의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 22의 헤테로아릴기이다.In one embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 22 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Ar5 및 Ar6는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 16의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 18의 헤테로아릴기이다.In one embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 16 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Ar5 및 Ar6는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환되고 N, O 또는 S를 포함하는 헤테로아릴기이다.In one embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a heteroaryl group which is substituted or unsubstituted and includes N, O or S.
본 명세서의 일 실시상태에 있어서, 상기 Ar5 및 Ar6는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 피롤, 퓨란, 티오펜 및 피리딘 중 1 이상을 포함하고 치환 또는 비치환된 헤테로아릴기이다.In one embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group containing at least one of pyrrole, furan, thiophene and pyridine.
본 명세서의 일 실시상태에 있어서, 상기 Ar5 및 Ar6는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 사슬형 알킬기, 사이클로알킬기, 알킬실릴기, 할로겐기, 니트릴기 또는 아릴기로 치환 또는 비치환된 아릴기; 또는 아릴기로 치환 또는 비치환된 헤테로아릴기이다.In one embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently an aryl unsubstituted or substituted with deuterium, a chain alkyl group, a cycloalkyl group, an alkylsilyl group, a halogen group, a nitrile group, or an aryl group group; Or a heteroaryl group unsubstituted or substituted with an aryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar5 및 Ar6는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 트리메틸실릴기, 메틸기, 사이클로헥실기, 플루오로기, 니트릴기, 페닐기 또는 나프틸기로 치환 또는 비치환된 아릴기; 또는 페닐기로 치환 또는 비치환된 헤테로아릴기이다.In one embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and are each independently substituted or unsubstituted with deuterium, trimethylsilyl group, methyl group, cyclohexyl group, fluoro group, nitrile group, phenyl group or naphthyl group Ring aryl group; Or a heteroaryl group unsubstituted or substituted with a phenyl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar5 및 Ar6는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 퓨라닐기; 치환 또는 비치환된 디벤조퓨라닐기; 치환 또는 비치환된 디벤조티오페닐기; 치환 또는 비치환된 나프토벤조퓨라닐기; 치환 또는 비치환된 나프토벤조티오페닐기; 치환 또는 비치환된 인돌로카바졸릴기; 또는 치환 또는 비치환된
Figure PCTKR2019006050-appb-I000029
이며, X11 및 X12는 각각 독립적으로 O 또는 S이다.In one embodiment of the present specification, Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted furanyl group; Substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophenyl group; A substituted or unsubstituted naphthobenzofuranyl group; A substituted or unsubstituted naphthobenzothiophenyl group; A substituted or unsubstituted indolocarbazolyl group; Or substituted or unsubstituted
Figure PCTKR2019006050-appb-I000029
And X 11 and X 12 are each independently O or S.
본 명세서의 일 실시상태에 있어서, 상기 a는 0이다.In one embodiment of the present specification, a is 0.
본 명세서의 일 실시상태에 있어서, 상기 R3는 수소이다.In one embodiment of the present specification, R3 is hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 화학식 H는 하기 화학식 H-1 또는 화학식 H-2로 표시된다.In one embodiment of the present specification, Chemical Formula H is represented by the following Chemical Formula H-1 or Chemical Formula H-2.
[화학식 H-1][Formula H-1]
Figure PCTKR2019006050-appb-I000030
Figure PCTKR2019006050-appb-I000030
[화학식 H-2][Formula H-2]
Figure PCTKR2019006050-appb-I000031
Figure PCTKR2019006050-appb-I000031
상기 화학식 H-1 및 화학식 H-2에 있어서,In Chemical Formula H-1 and Chemical Formula H-2,
L1, L2, R3 및 a의 정의는 화학식 H에서 정의한 바와 동일하고,The definitions of L1, L2, R3 and a are the same as defined in formula H,
Ar7 내지 Ar9는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이며,Ar7 to Ar9 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group,
HAr7는 치환 또는 비치환된 헤테로아릴기이다.HAr7 is a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar7 내지 Ar9는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 24의 아릴기이다.In one embodiment of the present specification, Ar7 to Ar9 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 24 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Ar7 내지 Ar9는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 20의 아릴기이다.In one embodiment of the present specification, Ar7 to Ar9 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Ar7 내지 Ar9는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 16의 아릴기이다.In one embodiment of the present specification, Ar7 to Ar9 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 16 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Ar7 내지 Ar9는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 사슬형 알킬기, 사이클로알킬기, 알킬실릴기, 할로겐기, 니트릴기 또는 아릴기로 치환 또는 비치환된 아릴기이다.In one embodiment of the present specification, Ar7 to Ar9 are the same as or different from each other, and are each independently substituted or unsubstituted with deuterium, a chain alkyl group, a cycloalkyl group, an alkylsilyl group, a halogen group, a nitrile group or an aryl group It is.
본 명세서의 일 실시상태에 있어서, 상기 Ar7 내지 Ar9는 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 트리메틸실릴기, 메틸기, 사이클로헥실기, 플루오로기, 니트릴기, 페닐기 또는 나프틸기로 치환 또는 비치환된 아릴기이다.In one embodiment of the present specification, Ar7 to Ar9 are the same as or different from each other, and are each independently substituted or unsubstituted with deuterium, trimethylsilyl, methyl, cyclohexyl, fluoro, nitrile, phenyl or naphthyl groups It is a substituted aryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar7 내지 Ar9는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 나프틸기; 또는 치환 또는 비치환된 페난트레닐기이다.In one embodiment of the present specification, Ar7 to Ar9 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted phenanthrenyl group.
본 명세서의 일 실시상태에 있어서, 상기 HAr7은 치환 또는 비치환된 탄소수 2 내지 26의 헤테로아릴기이다.In one embodiment of the present specification, HAr7 is a substituted or unsubstituted heteroaryl group having 2 to 26 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 HAr7은 치환 또는 비치환된 탄소수 2 내지 22의 헤테로아릴기이다.In one embodiment of the present specification, HAr7 is a substituted or unsubstituted C2-C22 heteroaryl group.
본 명세서의 일 실시상태에 있어서, 상기 HAr7은 치환 또는 비치환된 탄소수 2 내지 18의 헤테로아릴기이다.In one embodiment of the present specification, HAr7 is a substituted or unsubstituted heteroaryl group having 2 to 18 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 HAr7은 치환 또는 비치환되고 N, O 또는 S를 포함하는 헤테로아릴기이다.In one embodiment of the present specification, HAr7 is a heteroaryl group which is substituted or unsubstituted and includes N, O or S.
본 명세서의 일 실시상태에 있어서, 상기 HAr7은 피롤, 퓨란, 티오펜 및 피리딘 중 1 이상을 포함하고 치환 또는 비치환된 헤테로아릴기이다.In one embodiment of the present specification, HAr7 is a substituted or unsubstituted heteroaryl group including one or more of pyrrole, furan, thiophene and pyridine.
본 명세서의 일 실시상태에 있어서, 상기 HAr7은 아릴기로 치환 또는 비치환된 헤테로아릴기이다.In one embodiment of the present specification, HAr7 is a heteroaryl group unsubstituted or substituted with an aryl group.
본 명세서의 일 실시상태에 있어서, 상기 HAr7은 페닐기로 치환 또는 비치환된 헤테로아릴기이다.In one embodiment of the present specification, HAr7 is a heteroaryl group unsubstituted or substituted with a phenyl group.
본 명세서의 일 실시상태에 있어서, 상기 HAr7은 치환 또는 비치환된 퓨라닐기; 치환 또는 비치환된 디벤조퓨라닐기; 치환 또는 비치환된 디벤조티오페닐기; 치환 또는 비치환된 나프토벤조퓨라닐기; 치환 또는 비치환된 나프토벤조티오페닐기; 치환 또는 비치환된 인돌로카바졸릴기; 또는 치환 또는 비치환된
Figure PCTKR2019006050-appb-I000032
이며, X11 및 X12는 각각 독립적으로 O 또는 S이다.In one embodiment of the present specification, HAr7 is a substituted or unsubstituted furanyl group; Substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophenyl group; A substituted or unsubstituted naphthobenzofuranyl group; A substituted or unsubstituted naphthobenzothiophenyl group; A substituted or unsubstituted indolocarbazolyl group; Or substituted or unsubstituted
Figure PCTKR2019006050-appb-I000032
And X 11 and X 12 are each independently O or S.
본 명세서의 일 실시상태에 있어서, 상기 HAr7은 퓨라닐기; 디벤조퓨라닐기; 디벤조티오페닐기; 나프토벤조퓨라닐기; 나프토벤조티오페닐기; 인돌로카바졸릴기 또는
Figure PCTKR2019006050-appb-I000033
이며, X11 및 X12는 각각 독립적으로 O 또는 S이다.In one embodiment of the present specification, the HAr7 is a furanyl group; Dibenzofuranyl group; Dibenzothiophenyl group; Naphthobenzofuranyl group; Naphthobenzothiophenyl group; Indolocarbazolyl group or
Figure PCTKR2019006050-appb-I000033
And X 11 and X 12 are each independently O or S.
본 명세서의 일 실시상태에 있어서, 상기 발광층은 화학식 1로 표시되는 화합물을 포함하고, 상기 발광층은 상기 화학식 H-1로 표시되는 화합물 1종 또는 2종 이상을 더 포함한다.In one embodiment of the present specification, the light emitting layer includes a compound represented by Chemical Formula 1, and the light emitting layer further includes one or two or more compounds represented by Chemical Formula H-1.
본 명세서의 일 실시상태에 있어서, 상기 발광층은 화학식 1로 표시되는 화합물; 및 상기 화학식 H-1로 표시되는 화합물 2종을 포함한다. 상기 발광층에 포함되는 상기 화학식 H-1로 표시되는 2종의 화합물은 서로 동일하거나 상이할 수 있다.In one embodiment of the present specification, the light emitting layer is a compound represented by Formula 1; And two compounds represented by Chemical Formula H-1. The two compounds represented by Formula H-1 included in the emission layer may be the same or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 발광층은 화학식 1로 표시되는 화합물; 및 상기 화학식 H-2로 표시되는 화합물 1종 또는 2종 이상을 포함한다.In one embodiment of the present specification, the light emitting layer is a compound represented by Formula 1; And one or two or more compounds represented by Formula H-2.
본 명세서의 일 실시상태에 있어서, 상기 발광층은 화학식 1로 표시되는 화합물; 및 상기 화학식 H-2로 표시되는 화합물 2종을 포함한다. 상기 발광층에 포함되는 상기 화학식 H-2로 표시되는 2종의 화합물은 서로 동일하거나 상이할 수 있다.In one embodiment of the present specification, the light emitting layer is a compound represented by Formula 1; And two compounds represented by Formula H-2. The two compounds represented by Formula H-2 included in the emission layer may be the same or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 발광층은 상기 화학식 1로 표시되는 화합물; 상기 화학식 H-1로 표시되는 화합물 1종 이상; 및 상기 화학식 H-2로 표시되는 화합물 1종 이상을 포함한다.In one embodiment of the present specification, the light emitting layer is a compound represented by Chemical Formula 1; At least one compound represented by Formula H-1; And one or more compounds represented by Formula H-2.
본 명세서의 일 실시상태에 있어서, 상기 발광층은 상기 화학식 1로 표시되는 화합물; 상기 화학식 H-1로 표시되는 화합물; 및 상기 화학식 H-2로 표시되는 화합물을 포함한다.In one embodiment of the present specification, the light emitting layer is a compound represented by Chemical Formula 1; A compound represented by Chemical Formula H-1; And a compound represented by Chemical Formula H-2.
본 명세서의 일 실시상태에 있어서, 상기 화학식 H로 표시되는 화합물은 하기 화합물들 중에서 선택된 어느 하나이다. In one embodiment of the present specification, the compound represented by Formula H is any one selected from the following compounds.
Figure PCTKR2019006050-appb-I000034
Figure PCTKR2019006050-appb-I000034
Figure PCTKR2019006050-appb-I000035
Figure PCTKR2019006050-appb-I000035
Figure PCTKR2019006050-appb-I000036
Figure PCTKR2019006050-appb-I000036
본 명세서의 일 실시상태에 있어서, 상기 발광층은 화학식 1로 표시되는 화합물을 포함하고, 상기 화학식 1로 표시되는 화합물의 함량은 상기 발광층 총 100 중량부 대비 0.1 중량부 이상 15 중량부 이하이다.In one embodiment of the present specification, the light emitting layer includes a compound represented by Formula 1, and the content of the compound represented by Formula 1 is 0.1 part by weight or more and 15 parts by weight or less with respect to 100 parts by weight of the total light emitting layer.
본 명세서의 일 실시상태에 있어서, 상기 발광층은 화학식 1로 표시되는 화합물을 포함하고, 상기 화학식 1로 표시되는 화합물의 함량은 상기 발광층 총 100 중량부 대비 0.1 중량부 이상 10 중량부 이하이다.In one embodiment of the present specification, the light emitting layer includes a compound represented by Formula 1, and the content of the compound represented by Formula 1 is 0.1 part by weight or more and 10 parts by weight or less with respect to 100 parts by weight of the total light emitting layer.
본 명세서의 일 실시상태에 있어서, 상기 발광층은 상기 화학식 1로 표시되는 화합물 0.1 내지 15 중량부; 및 상기 화학식 H로 표시되는 화합물 85 중량부 내지 99.9 중량부를 포함한다.In one embodiment of the present specification, the light emitting layer is 0.1 to 15 parts by weight of the compound represented by Formula 1; And 85 parts by weight to 99.9 parts by weight of the compound represented by Formula H.
본 명세서의 일 실시상태에 있어서, 유기 발광 소자는 기판 상에 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 노말 구조(normal type)의 유기 발광 소자일 수 있다. In one embodiment of the present specification, the organic light emitting device may be an organic light emitting device having a normal structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
본 명세서의 일 실시상태에 있어서, 유기 발광 소자는 기판 상에 음극, 1층 이상의 유기물층 및 양극이 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다. In one embodiment of the present specification, the organic light emitting device may be an organic light emitting device having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
본 명세서의 일 실시상태에 있어서, 상기 제1 전극은 양극이고, 상기 제2 전극은 음극이다. In one embodiment of the present specification, the first electrode is an anode, and the second electrode is a cathode.
또 하나의 실시상태에 있어서, 상기 제1 전극은 음극이고, 상기 제2 전극은 양극이다. In another exemplary embodiment, the first electrode is a cathode and the second electrode is an anode.
본 명세서의 일 실시상태에 따른 유기 발광 소자의 구조는 도 1 내지 3에 예시되어 있다. The structure of the organic light emitting device according to the exemplary embodiment of the present specification is illustrated in FIGS. 1 to 3.
본 발명의 일 실시상태에 따른 유기 발광소자는 도 1에 도시한 바와 같이, 기판(1), 양극(2), 유기물층(3) 및 음극(4)으로 이루어질 수 있다. 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 유기물층(3)에 포함된다.As shown in FIG. 1, an organic light emitting diode according to an exemplary embodiment of the present invention may include a substrate 1, an anode 2, an organic material layer 3, and a cathode 4. In one embodiment, the compound represented by Formula 1 is included in the organic material layer (3).
본 발명의 일 실시상태에 따른 유기 발광 소자는 도 2에 도시된 바와 같이 기판(1), 양극(2), 정공 주입층(5), 정공 수송층(6), 정공 조절층(7), 발광층(8), 전자 수송층(9), 전자 주입층(10) 및 음극(4)으로 이루어질 수 있다. 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 발광층(8)에 포함된다. 다른 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 정공 수송층(5), 정공 수송층(6) 및 정공 조절층(7) 중 어느 하나의 층에 포함된다. As shown in FIG. 2, the organic light emitting diode according to the exemplary embodiment of the present invention includes a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a hole control layer 7, and a light emitting layer. 8, the electron transport layer 9, the electron injection layer 10 and the cathode (4). In one embodiment, the compound represented by Formula 1 is included in the light emitting layer (8). In another embodiment, the compound represented by Formula 1 is included in any one of the hole transport layer 5, the hole transport layer 6 and the hole control layer (7).
도 3은 기판(1), 양극(2), 정공 주입층(5), 제1 정공 수송층(6a), 제2 정공 수송층(6b), 발광층(8), 전자 주입 및 수송층(11) 및 음극(4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 발광층(8)에 포함된다.3 shows a substrate 1, an anode 2, a hole injection layer 5, a first hole transport layer 6a, a second hole transport layer 6b, a light emitting layer 8, an electron injection and transport layer 11, and a cathode. The example of the organic light emitting element which consists of (4) is shown. In one embodiment, the compound represented by Formula 1 is included in the light emitting layer (8).
그러나, 본 명세서의 일 실시상태에 따른 유기 발광 소자의 구조는 도 1 내지 도 3에 한정되지 않고, 하기의 구조 중 어느 하나일 수 있다.However, the structure of the organic light emitting diode according to the exemplary embodiment of the present specification is not limited to FIGS. 1 to 3, and may be any one of the following structures.
(1) 양극/정공수송층/발광층/음극(1) anode / hole transport layer / light emitting layer / cathode
(2) 양극/정공주입층/정공수송층/발광층/음극(2) Anode / hole injection layer / hole transport layer / light emitting layer / cathode
(3) 양극/정공수송층/발광층/전자수송층/음극(3) Anode / hole transport layer / light emitting layer / electron transport layer / cathode
(4) 양극/정공수송층/발광층/전자수송층/전자주입층/음극(4) Anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode
(5) 양극/정공주입층/정공수송층/발광층/전자수송층/음극(5) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode
(6) 양극/정공주입층/정공수송층/발광층/전자수송층/전자주입층/음극(6) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode
(7) 양극/정공수송층/정공조절층/발광층/전자수송층/음극(7) Anode / hole transport layer / hole control layer / light emitting layer / electron transport layer / cathode
(8) 양극/정공수송층/정공조절층/발광층/전자수송층/전자주입층/음극(8) Anode / hole transport layer / hole control layer / light emitting layer / electron transport layer / electron injection layer / cathode
(9) 양극/정공주입층/정공수송층/정공조절층/발광층/전자수송층/음극(9) Anode / hole injection layer / hole transport layer / hole control layer / light emitting layer / electron transport layer / cathode
(10) 양극/정공주입층/정공수송층/정공조절층/발광층/전자수송층/전자주입층/음극(10) Anode / hole injection layer / hole transport layer / hole control layer / light emitting layer / electron transport layer / electron injection layer / cathode
(11) 양극/정공수송층/발광층/전자조절층/전자수송층/음극(11) Anode / hole transport layer / light emitting layer / electron control layer / electron transport layer / cathode
(12) 양극/정공수송층/발광층/전자조절층/전자수송층/전자주입층/음극(12) Anode / hole transport layer / light emitting layer / electron control layer / electron transport layer / electron injection layer / cathode
(13) 양극/정공주입층/정공수송층/발광층/전자조절층/전자수송층/음극(13) Anode / hole injection layer / hole transport layer / light emitting layer / electron control layer / electron transport layer / cathode
(14) 양극/정공주입층/정공수송층/발광층/전자조절층/전자수송층/전자주입층/음극(14) Anode / hole injection layer / hole transport layer / light emitting layer / electron control layer / electron transport layer / electron injection layer / cathode
상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 서로 동일한 물질 또는 다른 물질로 형성될 수 있다. When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
예컨대, 본 명세서의 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시킴으로써 제조할 수 있다. 이 때 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 물리적 증착 방법(PVD, physical Vapor Deposition)을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, by using a physical vapor deposition (PVD, physical vapor deposition) such as sputtering (e-beam evaporation), by depositing a metal or conductive metal oxide or alloys thereof on the substrate It can be prepared by forming an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
또한, 상기 화학식 1로 표시되는 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.In addition, the compound represented by Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
이와 같은 방법 외에도, 기판 상에 음극 물질로부터 유기물층, 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다 (국제 특허 출원 공개 제 2003/012890호). 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to such a method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890). However, the manufacturing method is not limited thereto.
상기 양극 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 양극 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. As the anode material, a material having a large work function is usually preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
상기 음극 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 음극 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
상기 정공 주입층은 전극으로부터 수취받은 정공을 발광층 또는 발광층쪽으로 구비된 인접한 층에 주입하는 층이다. 상기 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입 효과, 발광층 또는 발광 재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 엑시톤의 전자 주입층 또는 전자 주입 재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물을 사용하는 것이 바람직하다. 상기 정공 주입 물질의 HOMO(highest occupied molecular orbital)는 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 상기 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone)계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. The hole injection layer is a layer for injecting holes received from the electrode into the light emitting layer or an adjacent layer provided toward the light emitting layer. The hole injection material has the ability to transport holes, has an effect of hole injection at the anode, an excellent hole injection effect on the light emitting layer or the light emitting material, and transfers excitons generated from the light emitting layer to the electron injection layer or the electron injection material. It is preferable to use the compound which prevents and is excellent in thin film formation ability. The highest occupied molecular orbital (HOMO) of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer. Specific examples of the hole injection material include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene Organic, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
상기 정공 수송층은 양극이나 정공 주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층이다. 상기 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 상기 정공 수송 물질의 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. The hole transport layer is a layer that receives holes from an anode or a hole injection layer and transports holes to the light emitting layer. As the hole transporting material, a material capable of transporting holes from the anode or the hole injection layer to be transferred to the light emitting layer is suitable. Specific examples of the hole transport material include, but are not limited to, an arylamine-based organic material, a conductive polymer, a block copolymer having a conjugated portion and a non-conjugated portion together, and the like.
상기 정공 조절층은 발광층으로주터 전자가 양극으로 유입되는 것을 방지하고 발광층으로 유입되는 정공의 흐름을 조절하여 소자 전체의 성능을 조절하는 층이다. 상기 정공 조절 물질로는 발광층으로부터 양극으로의 전자의 유입을 방지하고, 발광층 또는 발광 재료에 대하여 주입되는 정공의 흐름을 조절하는 능력을 갖는 화합물이 바람직하다. 일 실시상태에 있어서, 정공 조절층에는 아릴아민 계열의 유기물이 사용될 수 있으나, 이에 한정되는 것은 아니다.The hole control layer is a layer for preventing the flow of the electrons to the anode to the light emitting layer and to control the flow of holes flowing into the light emitting layer to control the performance of the entire device. As the hole control material, a compound having the ability to prevent the inflow of electrons from the light emitting layer to the anode and to control the flow of holes injected to the light emitting layer or the light emitting material is preferable. In one embodiment, an arylamine-based organic material may be used as the hole control layer, but is not limited thereto.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 1층 또는 2층 이상의 발광층을 포함할 수 있다. 상기 1층 또는 2층 이상의 발광층에 있어서, 상기 발광 물질로 상기 화학식 1로 표시되는 화합물을 1층 또는 2층 이상의 발광층에 사용할 수 있다. 상기 화학식 1로 표시되는 화합물을 포함하지 않는 발광층은 화학식 1의 화합물 이외의 발광 물질을 포함할 수 있다.In one embodiment of the present specification, the organic light emitting device may include one or two or more light emitting layers. In the light emitting layer of one or two or more layers, the compound represented by Chemical Formula 1 may be used as the light emitting material in one or two or more light emitting layers. The emission layer that does not include the compound represented by Formula 1 may include a light emitting material other than the compound of Formula 1.
상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 상기 발광 물질의 구체적인 예로는 8-하이드록시퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-하이드록시벤조퀴놀린-금속 화합물; 벤즈옥사졸, 벤조티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌, 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다. The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Specific examples of the light emitting material include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzothiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
일 실시상태에 있어서, 상기 발광층의 발광 물질로서 호스트/도판트계를 사용할 수 있다. 본 발명의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물을 도판트로 포함하는 발광층은 상기 화학식 H로 표시되는 화합물을 호스트 물질로 상기 발광층에 포함할 수 있다. 본 명세서의 일 실시상태에 있어서 상기 화학식 1로 표시되는 화합물이 포함되는 발광층 이외의 발광층은 하기의 호스트 재료 또는 도판트 재료를 포함할 수 있다.In one embodiment, a host / dopant system may be used as a light emitting material of the light emitting layer. In an exemplary embodiment of the present invention, the light emitting layer including the compound represented by Chemical Formula 1 as a dopant may include the compound represented by Chemical Formula H as a host material in the light emitting layer. In an exemplary embodiment of the present specification, the light emitting layer other than the light emitting layer including the compound represented by Chemical Formula 1 may include the following host material or dopant material.
상기 발광층의 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 파이렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다. The host material of the light emitting layer may be a condensed aromatic ring derivative or a hetero ring-containing compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladders. Type furan compounds, pyrimidine derivatives, and the like, but is not limited thereto.
상기 발광층의 도판트 재료로는 방향족 아민 유도체, 스티릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다. 상기 방향족 아민 유도체로는 치환 또는 비치환된 아릴아민기를 갖는 축합 방향족환 유도체로서, 아릴아민기를 갖는 파이렌, 안트라센, 크라이센, 페리플란텐 등을 사용할 수 있다. 상기 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환된 화합물을 사용할 수 있다. 상기 스티릴아민 화합물의 예로는 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 상기 금속 착체로는 이리듐 착체, 백금 착체 등을 사용할 수 있으나, 이에 한정되지 않는다.The dopant material of the light emitting layer includes an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex, and the like. As the aromatic amine derivative, pyrene, anthracene, chrysene, periplanthene and the like having an arylamine group may be used as a condensed aromatic ring derivative having a substituted or unsubstituted arylamine group. As the styrylamine compound, a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine may be used. Examples of the styrylamine compound include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like. The metal complex may be an iridium complex, a platinum complex, or the like, but is not limited thereto.
상기 전자 조절층은 발광층으로부터 정공이 음극으로 유입되는 것을 차단하고 발광층으로 유입되는 전자를 조절하여 소자 전체의 성능을 조절하는 층이다. 전자 조절 물질로는 발광층으로부터 음극으로의 정공의 유입을 방지하고, 발광층 또는 발광 재료에 대하여 주입되는 전자를 조절하는 능력을 갖는 화합물이 바람직하다. 전자 조절 물질로는 소자 내 사용되는 유기물층의 구성에 따라 적절한 물질을 사용할 수 있다. 상기 전자 조절층은 발광층과 음극 사이에 위치하며, 바람직하게는 발광층에 직접 접하여 구비된다.The electron control layer is a layer that blocks the flow of holes from the light emitting layer to the cathode and controls the performance of the entire device by adjusting the electrons flowing into the light emitting layer. As the electron adjusting material, a compound having the ability to prevent the inflow of holes from the light emitting layer to the cathode and to control the electrons injected into the light emitting layer or the light emitting material is preferable. As the electron control material, an appropriate material may be used according to the configuration of the organic material layer used in the device. The electron control layer is positioned between the light emitting layer and the cathode, preferably provided in direct contact with the light emitting layer.
상기 전자 수송층은 전자 주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층이다. 상기 전자 수송 물질로는 음극이나 전자 주입층으로부터 전자를 잘 주입받아 발광층으로 옮겨줄 수 있는 물질로 전자에 대한 이동성이 큰 물질이 적합하다. 상기 전자 수송 물질의 예로는 8-하이드록시퀴놀린의 Al착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 하이드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 상기 전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 음극 물질과 함께 사용할 수 있다. 일 실시상태에 있어서, 상기 음극 물질로는 낮은 일함수를 가지는 물질; 및 알루미늄층 또는 실버층을 사용할 수 있다. 상기 낮은 일함수를 가지는 물질의 예로는 세슘, 바륨, 칼슘, 이테르븀 및 사마륨 등이 있으며, 상기 물질로 층을 형성한 후 알루미늄층 또는 실버층을 상기 층 위에 형성할 수 있다.The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer. As the electron transporting material, a material capable of injecting electrons well from a cathode or an electron injection layer and transferring the electrons to a light emitting layer is suitable. Examples of the electron transporting material include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired negative electrode material as used in the prior art. In one embodiment, the negative electrode material includes a material having a low work function; And aluminum layers or silver layers. Examples of the material having a low work function include cesium, barium, calcium, ytterbium, and samarium, and after forming a layer from the material, an aluminum layer or a silver layer may be formed on the layer.
상기 전자 주입층은 전극으로부터 수취받은 전자를 발광층에 주입하는 층이다. 상기 전자 주입 물질로는 전자를 수송하는 능력을 갖고, 음극으로부터의 전자 주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자 주입 효과를 가지며, 발광층에서 생성된 엑시톤의 정공 주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물을 사용하는 것이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 함질소 5원환 유도체 등이 있으나, 이에 한정되지 않는다. The electron injection layer is a layer for injecting electrons received from the electrode into the light emitting layer. The electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, excellent electron injection effect to the light emitting layer or the light emitting material, and prevents the movement of excitons generated in the light emitting layer to the hole injection layer, Moreover, it is preferable to use the compound excellent in the thin film formation ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
본 명세서에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present specification may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
이하, 본 발명에 따르는 실시예 및 본 발명에 따르지 않는 비교예를 통하여 본 발명을 보다 상세히 설명하나, 본 발명의 범위가 하기 제시된 실시예에 의해 제한되는 것은 아니다.Hereinafter, the present invention will be described in more detail through examples according to the present invention and comparative examples not according to the present invention, but the scope of the present invention is not limited to the examples given below.
합성예 1. 화합물 1의 합성Synthesis Example 1 Synthesis of Compound 1
중간체 1의 합성Synthesis of Intermediate 1
Figure PCTKR2019006050-appb-I000037
Figure PCTKR2019006050-appb-I000037
질소 분위기하에서 화합물 A-1 18 g, 화합물 B-1 20 g, 탄산 칼륨(potassium carbonate) 28 g, 디옥산 400 mL 및 물 100 mL를 넣은 후 테트라키스(트리페닐포스핀)팔라듐(0)(Pd(PPh3)4) 2.3 g을 첨가한 후, 120 ℃에서 가열하고 8시간 동안 교반하였다. 반응 종료 후 반응액을 실온까지 냉각시키고, 물과 에틸 아세테이트를 가하여 분액한 후 MgSO4(anhydrous) 처리하여 여과하였다. 여과한 용액을 감압하에서 증류제거하고 재결정(ethylacetate/hexane)으로 정제하여 중간체 1 20 g을 수득하였다. (수율 74%, Mass [M+]=407) In a nitrogen atmosphere, 18 g of compound A-1, 20 g of compound B-1, 28 g of potassium carbonate, 400 mL of dioxane and 100 mL of water were added, followed by tetrakis (triphenylphosphine) palladium (0) ( 2.3 g of Pd (PPh 3 ) 4 ) were added, then heated at 120 ° C. and stirred for 8 h. After the reaction was completed, the reaction solution was cooled to room temperature, water and ethyl acetate were added, the solution was separated, and the mixture was filtered with MgSO 4 (anhydrous). The filtered solution was distilled off under reduced pressure and purified by recrystallization (ethylacetate / hexane) to give 20 g of intermediate 1. (Yield 74%, Mass [M + ] = 407)
중간체 2의 합성Synthesis of Intermediate 2
Figure PCTKR2019006050-appb-I000038
Figure PCTKR2019006050-appb-I000038
질소 분위기하에서 중간체 1 20 g에 클로로포름 500 mL를 넣은 후, 0 ℃에서 보론 트리브로마이드 14 mL를 천천히 적가 후 6시간동안 교반하였다. 반응 종료 후 물을 가하여 클로로포름과 분액한 후, MgSO4(anhydrous) 처리하여 여과하였다. 여과한 용액을 감압하에서 증류제거하고 저온에서 재결정(Ethylacetate/hexane)으로 정제하여 화합물 중간체 2 15 g을 수득하였다. (수율 81%, Mass [M+]=379)500 mL of chloroform was added to 20 g of Intermediate 1 under a nitrogen atmosphere, and 14 mL of boron tribromide was slowly added dropwise at 0 ° C., followed by stirring for 6 hours. After completion of the reaction, water was added, the solution was separated with chloroform, and then filtered through MgSO 4 (anhydrous) treatment. The filtered solution was distilled off under reduced pressure and purified by recrystallization (Ethylacetate / hexane) at low temperature to give 15 g of compound intermediate 2. (Yield 81%, Mass [M + ] = 379)
중간체 4의 합성Synthesis of Intermediate 4
Figure PCTKR2019006050-appb-I000039
Figure PCTKR2019006050-appb-I000039
질소 분위기하에서 중간체 2 15 g과 탄산칼륨 27 g을 N-디메틸포름아마이드(N-dimethylformamide) 400 mL에 넣고 160 ℃에서 2시간동안 교반하여 중간체 3을 합성하였다. 반응 종료 후 반응액을 실온까지 냉각시키고, 바로 퍼플루오로부탄설포닐 플루오라이드(perfluorobutanesulfonyl floride) 18 mL를 첨가하여 1시간동안 교반하였다. 반응이 완료한 후, 물과 에틸아세테이트를 가하여 분액한 후 MgSO4(anhydrous) 처리하여 여과하였다. 여과한 용액을 감압 하에서 증류제거하고 재결정 (톨루엔/헥산)으로 정제하여 중간체 4 14 g을 수득하였다. (수율 55%, Mass [M+]=641)15 g of intermediate 2 and 27 g of potassium carbonate were added to 400 mL of N-dimethylformamide in a nitrogen atmosphere, and stirred at 160 ° C. for 2 hours to synthesize intermediate 3. After the reaction was completed, the reaction solution was cooled to room temperature, and 18 mL of perfluorobutanesulfonyl floride was added thereto, followed by stirring for 1 hour. After the reaction was completed, water and ethyl acetate were added to the solution, and the mixture was filtered with MgSO 4 (anhydrous). The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene / hexane) to give 14 g of intermediate 4. (Yield 55%, Mass [M + ] = 641)
화합물 1의 합성Synthesis of Compound 1
Figure PCTKR2019006050-appb-I000040
Figure PCTKR2019006050-appb-I000040
질소 분위기하에서 중간체 4 5 g, 화합물 a-1 7.7 g 및 인산 칼륨(potassium phosphate) 10 g에 자일렌 200 mL를 넣고, 비스(디벤질리덴아세톤)팔라듐(0)(Bis(dibenzylideneacetone)palladium(0)) 0.19 g과 Xphos 0.32 g을 자일렌에 녹여 반응액에 천천히 적가한다. 반응액은 150 ℃에서 가열하고 24시간동안 교반하였다. 반응 종료 후 반응액을 실온까지 냉각시키고, 물 및 NaCl 용액을 가하여 분액한 후 MgSO4(anhydrous) 처리하여 여과하였다. 여과한 용액을 감압하에서 증류제거하고 재결정(toluene/hexane)으로 정제하여 화합물 1 7.6 g을 수득하였다. (수율 65%, Mass [M+]=705)In a nitrogen atmosphere, 200 mL of xylene was added to 5 g of intermediate 4, 7.7 g of compound a-1 and 10 g of potassium phosphate, and bis (dibenzylideneacetone) palladium (0) (Bis (dibenzylideneacetone) palladium (0) )) Dissolve 0.19 g and Xphos 0.32 g in xylene and slowly add to the reaction solution. The reaction solution is 150 Heat at C and stir for 24 h. After the completion of the reaction, the reaction solution was cooled to room temperature, water and NaCl solution were added to the solution, followed by MgSO 4 (anhydrous) treatment and filtration. The filtered solution was distilled off under reduced pressure and purified by recrystallization (toluene / hexane) to give 7.6 g of compound 1. (Yield 65%, Mass [M + ] = 705)
합성예 2. 화합물 2의 합성Synthesis Example 2 Synthesis of Compound 2
Figure PCTKR2019006050-appb-I000041
Figure PCTKR2019006050-appb-I000041
화합물 a-1 대신 화합물 a-2 2.6 g을 이용한 것을 제외하고는 화합물 1의 합성법과 동일한 방법으로 화합물 2 2.1 g을 수득하였다. (수율 54%, Mass [M+]=900)2.1 g of Compound 2 was obtained by the same method as the synthesis method of Compound 1, except that 2.6 g of Compound a-2 was used instead of Compound a-1. (Yield 54%, Mass [M + ] = 900)
합성예 3. 화합물 3의 합성Synthesis Example 3 Synthesis of Compound 3
중간체 5의 합성Synthesis of Intermediate 5
Figure PCTKR2019006050-appb-I000042
Figure PCTKR2019006050-appb-I000042
중간체 1의 합성에서 화합물 B-1 대신 화합물 B-2 10 g을 사용한 것을 제외하고 중간체 1의 합성법과 동일한 방법으로 중간체 5 8.6 g을 수득하였다. (수율 66 %, Mass [M+]=457) 8.6 g of intermediate 5 was obtained by the same method as the synthesis of intermediate 1, except that 10 g of compound B-2 was used instead of compound B-1 in the synthesis of intermediate 1. (Yield 66%, Mass [M + ] = 457)
중간체 6의 합성Synthesis of Intermediate 6
Figure PCTKR2019006050-appb-I000043
Figure PCTKR2019006050-appb-I000043
중간체 2의 합성에서 중간체 1 대신 중간체 5 8 g을 사용한 것을 제외하고 중간체 2의 합성법과 동일한 방법으로 중간체 6 5.6 g을 수득하였다. (수율 75%, Mass [M+]=429)5.6 g of Intermediate 6 was obtained by the same method as the synthesis of Intermediate 2, except that 8 g of Intermediate 5 was used instead of Intermediate 1 in the synthesis of Intermediate 2. (Yield 75%, Mass [M + ] = 429)
중간체 8의 합성Synthesis of Intermediate 8
Figure PCTKR2019006050-appb-I000044
Figure PCTKR2019006050-appb-I000044
중간체 4의 합성에서 중간체 2 대신 중간체 6 5.5 g을 사용한 것을 제외하고 중간체 4의 합성법과 동일한 방법으로 중간체 8 5.1 g을 수득하였다. (수율 58 %, Mass [M+]=691)5.1 g of intermediate 8 was obtained by the same method as the synthesis of intermediate 4, except that 5.5 g of intermediate 6 was used instead of intermediate 2 in the synthesis of intermediate 4. (Yield 58%, Mass [M + ] = 691)
화합물 3의 합성Synthesis of Compound 3
Figure PCTKR2019006050-appb-I000045
Figure PCTKR2019006050-appb-I000045
화합물 1의 합성에서 중간체 4 대신 중간체 8 3.g을 사용하고, 화합물 a-1 대신 화합물 a-3 2.9 g을 사용한 것을 제외하고 화합물 1의 합성법과 동일한 방법으로 화합물 3 2.7 g을 수득하였다. (수율 60 %, Mass [M+]=1030)2.7 g of Compound 3 was obtained by the same method as the synthesis of Compound 1, except that 3.g of Intermediate 8 was used instead of Intermediate 4 in the synthesis of Compound 1, and 2.9 g of Compound a-3 was used instead of Compound a-1. (Yield 60%, Mass [M + ] = 1030)
합성예 4. 화합물 4의 합성Synthesis Example 4 Synthesis of Compound 4
Figure PCTKR2019006050-appb-I000046
Figure PCTKR2019006050-appb-I000046
화합물 1의 합성에서 중간체 4 대신 중간체 8 2 g을 사용하고, 화합물 a-1 대신 화합물 a-4 1.9 g을 사용한 것을 제외하고는 화합물 1의 합성법과 동일한 방법으로 화합물 4 1.6 g을 수득하였다. (수율 54 %, Mass [M+]=1018) 1.6 g of Compound 4 was obtained by the same method as the synthesis of Compound 1, except that 2 g of Intermediate 8 was used instead of Intermediate 4 in the synthesis of Compound 1, and 1.9 g of Compound a-4 was used instead of Compound a-1. (Yield 54%, Mass [M + ] = 1018)
합성예 5. 화합물 5의 합성Synthesis Example 5 Synthesis of Compound 5
중간체 9의 합성Synthesis of Intermediate 9
Figure PCTKR2019006050-appb-I000047
Figure PCTKR2019006050-appb-I000047
중간체 1의 합성에서 화합물 A-1 대신 화합물 A-2 8 g을 사용하고, 화합물 B-1 대신 화합물 B-3 10 g을 사용한 것을 제외하고 중간체 1의 합성법과 동일한 방법으로 중간체 9 9.1 g을 수득하였다. (수율 70 %, Mass [M+]=457) 9.1 g of intermediate 9 was obtained by the same method as the synthesis of intermediate 1, except that 8 g of compound A-2 was used instead of compound A-1 in the synthesis of intermediate 1, and 10 g of compound B-3 was used instead of compound B-1. It was. (Yield 70%, Mass [M + ] = 457)
중간체 10의 합성Synthesis of Intermediate 10
Figure PCTKR2019006050-appb-I000048
Figure PCTKR2019006050-appb-I000048
중간체 2의 합성에서 중간체 1 대신 중간체 9 9 g을 사용한 것을 제외하고 중간체 2의 합성법과 동일한 방법으로 중간체 10 6.2 g을 수득하였다. (수율 73 %, Mass [M+]=429)6.2 g of intermediate 10 was obtained by the same method as the synthesis of intermediate 2, except that 9 9 g of intermediate 9 was used instead of intermediate 1 in the synthesis of intermediate 2. (Yield 73%, Mass [M + ] = 429)
중간체 12의 합성Synthesis of Intermediate 12
Figure PCTKR2019006050-appb-I000049
Figure PCTKR2019006050-appb-I000049
중간체 4의 합성에서 중간체 2 대신 중간체 10 6 g을 사용한 것을 제외하고 중간체 4의 합성법과 동일한 방법으로 중간체 12 5.3 g을 수득하였다. (수율 55 %, Mass [M+]=691)5.3 g of intermediate 12 was obtained by the same method as the synthesis of intermediate 4, except that 6 10 g of intermediate 10 was used instead of intermediate 2 in the synthesis of intermediate 4. (Yield 55%, Mass [M + ] = 691)
화합물 5의 합성Synthesis of Compound 5
Figure PCTKR2019006050-appb-I000050
Figure PCTKR2019006050-appb-I000050
화합물 1의 합성에서 중간체 4 대신 중간체 12 3 g을 사용하고, 화합물 a-1 대신 화합물 a-5 2.9 g을 사용한 것을 제외하고 화합물 1의 합성법과 동일한 방법으로 화합물 5 2.9 g을 수득하였다. (수율 66 %, Mass [M+]=1018)2.9 g of Compound 5 was obtained by the same method as the synthesis of Compound 1, except that 3 g of Intermediate 12 was used instead of Intermediate 4 in the synthesis of Compound 1, and 2.9 g of Compound a-5 was used instead of Compound a-1. (Yield 66%, Mass [M + ] = 1018)
합성예 6. 화합물 6의 합성Synthesis Example 6 Synthesis of Compound 6
Figure PCTKR2019006050-appb-I000051
Figure PCTKR2019006050-appb-I000051
화합물 1의 합성에서 중간체 4 대신 중간체 12 2.8 g을 사용하고, 화합물 a-1 대신 화합물 a-6 1.8 g을 사용한 것을 제외하고 화합물 1의 합성법과 동일한 방법으로 화합물 6 1.8 g을 수득하였다. (수율 67%, Mass [M+]=808)1.8 g of compound 6 was obtained by the same method as the synthesis method of compound 1, except that 2.8 g of intermediate 12 was used instead of intermediate 4 in the synthesis of compound 1, and 1.8 g of compound a-6 was used instead of compound a-1. (Yield 67%, Mass [M + ] = 808)
합성예 7. 화합물 7의 합성Synthesis Example 7 Synthesis of Compound 7
중간체 13의 합성Synthesis of Intermediate 13
Figure PCTKR2019006050-appb-I000052
Figure PCTKR2019006050-appb-I000052
중간체 1의 합성에서 화합물 A-1 대신 화합물 A-3 8 g을 사용하고, 화합물 B-1 대신 화합물 B-4 10 g을 사용한 것을 제외하고 중간체 1의 합성법과 동일한 방법으로 중간체 13 8.4 g을 수득하였다. (수율 64 %, Mass [M+]=457) 8.4 g of intermediate 13 was obtained by the same method as the synthesis of Intermediate 1, except that 8 g of Compound A-3 was used instead of Compound A-1 and 10 g of Compound B-4 was used instead of Compound B-1 in the synthesis of Intermediate 1. It was. (Yield 64%, Mass [M + ] = 457)
중간체 14의 합성Synthesis of Intermediate 14
Figure PCTKR2019006050-appb-I000053
Figure PCTKR2019006050-appb-I000053
중간체 2의 합성에서 중간체 1 대신 중간체 13 8 g을 사용한 것을 제외하고 중간체 2의 합성법과 동일한 방법으로 중간체 14 5.2 g을 수득하였다. (수율 69 %, Mass [M+]=429)5.2 g of intermediate 14 was obtained by the same method as the synthesis of intermediate 2, except that 8 13 g of Intermediate 13 was used instead of Intermediate 1 in the synthesis of Intermediate 2. (Yield 69%, Mass [M + ] = 429)
중간체 16의 합성Synthesis of Intermediate 16
Figure PCTKR2019006050-appb-I000054
Figure PCTKR2019006050-appb-I000054
중간체 4의 합성에서 중간체 2 대신 중간체 14 5 g을 사용한 것을 제외하고 중간체 4의 합성법과 동일한 방법으로 중간체 16 4.8 g을 수득하였다. (수율 60 %, Mass [M+]=691)4.8 g of intermediate 16 was obtained by the same method as the synthesis of intermediate 4, except that 5 14 g of Intermediate 14 was used instead of Intermediate 2 in the synthesis of Intermediate 4. (Yield 60%, Mass [M + ] = 691)
화합물 7의 합성Synthesis of Compound 7
Figure PCTKR2019006050-appb-I000055
Figure PCTKR2019006050-appb-I000055
화합물 1의 합성에서 중간체 4 대신 중간체 16 2.4 g을 사용하고, 화합물 a-1 대신 화합물 a-7 1.9 g 을 사용한 것을 제외하고 화합물 1의 합성법과 동일한 방법으로 화합물 7 1.9 g을 수득하였다. (수율 58 %, Mass [M+]=900)1.9 g of compound 7 was obtained by the same method as the synthesis method of compound 1, except that 2.4 g of Intermediate 16 was used instead of Intermediate 4 in the synthesis of Compound 1, and 1.9 g of Compound a-7 was used instead of Compound a-1. (Yield 58%, Mass [M + ] = 900)
합성예 8. 화합물 8의 합성Synthesis Example 8 Synthesis of Compound 8
Figure PCTKR2019006050-appb-I000056
Figure PCTKR2019006050-appb-I000056
화합물 1의 합성에서 중합체 4 대신 중간체 16 2.4 g을 사용하고, 화합물 a-1 대신 화합물 a-8 2.2 g을 이용하여 화합물 1의 합성법과 동일한 방법으로 화합물 8 1.9 g을 수득하였다. (수율 56 %, Mass [M+]=986)In the synthesis of Compound 1, 1.9 g of Compound 8 was obtained by the same method as the synthesis of Compound 1, using 2.4 g of Intermediate 16 instead of Polymer 4 and 2.2 g of Compound a-8 instead of Compound a-1. (Yield 56%, Mass [M + ] = 986)
합성예 9. 화합물 9의 합성Synthesis Example 9. Synthesis of Compound 9
중간체 17의 합성Synthesis of Intermediate 17
Figure PCTKR2019006050-appb-I000057
Figure PCTKR2019006050-appb-I000057
중간체 1의 합성에서 화합물 A-1 대신 화합물 A-4 8 g을 사용하고, 화합물 B-1 대신 화합물 B-5 10 g을 사용한 것을 제외하고 중간체 1의 합성법과 동일한 방법으로 중간체 17 8.4 g을 수득하였다. (수율 64 %, Mass [M+]=457)8.4 g of intermediate 17 was obtained by the same method as the synthesis of Intermediate 1, except that 8 g of Compound A-4 was used instead of Compound A-1 and 10 g of Compound B-5 was used instead of Compound B-1 in the synthesis of Intermediate 1. It was. (Yield 64%, Mass [M + ] = 457)
중간체 18의 합성Synthesis of Intermediate 18
Figure PCTKR2019006050-appb-I000058
Figure PCTKR2019006050-appb-I000058
중간체 2의 합성에서 중간체 1 대신 중간체 17 8 g을 사용한 것을 제외하고 중간체 2의 합성법과 동일한 방법으로 중간체 18 5.7 g을 수득하였다. (수율 76 %, Mass [M+]=429)5.7 g of intermediate 18 was obtained by the same method as the synthesis of intermediate 2, except that 8 17 g of intermediate 17 was used instead of intermediate 1 in the synthesis of intermediate 2. (Yield 76%, Mass [M + ] = 429)
중간체 20의 합성Synthesis of Intermediate 20
Figure PCTKR2019006050-appb-I000059
Figure PCTKR2019006050-appb-I000059
중간체 4의 합성에서 중간체 2 대신 중간체 18 5 g을 사용한 것을 제외하고 중간체 4의 합성법과 동일한 방법으로 중간체 20 4.6g을 수득하였다. (수율 57 %, Mass [M+]=691)4.6 g of Intermediate 20 was obtained by the same method as the synthesis of Intermediate 4, except that 5 g of Intermediate 18 was used instead of Intermediate 2 in the synthesis of Intermediate 4. (Yield 57%, Mass [M + ] = 691)
화합물 9의 합성Synthesis of Compound 9
Figure PCTKR2019006050-appb-I000060
Figure PCTKR2019006050-appb-I000060
화합물 1의 합성에서 중간체 4 대신 중간체 20 2.5g을 사용하고, 화합물 a-1 대신 화합물 a-9 1.8 g을 사용한 것을 제외하고 화합물 1의 합성법과 동일한 방법으로 화합물 9 1.6 g을 수득하였다. (수율 52 %, Mass [M+]=858)1.6 g of compound 9 was obtained by the same method as the synthesis method of compound 1, except that 2.5 g of intermediate 20 was used instead of intermediate 4 in the synthesis of compound 1, and 1.8 g of compound a-9 was used instead of compound a-1. (Yield 52%, Mass [M + ] = 858)
합성예 10. 화합물 10의 합성Synthesis Example 10 Synthesis of Compound 10
Figure PCTKR2019006050-appb-I000061
Figure PCTKR2019006050-appb-I000061
화합물 1의 합성에서 중합체 4 대신 중간체 20 2 g을 사용하고, 화합물 a-1 대신 화합물 a-10 1.2 g을 사용한 것을 제외하고 화합물 1의 합성법과 동일한 방법으로 화합물 10 1.4 g을 수득하였다. (수율 62 %, Mass [M+]=777)1.4 g of compound 10 was obtained by the same method as the synthesis method of compound 1, except that 2 g of intermediate 20 was used instead of polymer 4 in the synthesis of compound 1 and 1.2 g of compound a-10 was used instead of compound a-1. (Yield 62%, Mass [M + ] = 777)
합성예 11. 화합물 11의 합성Synthesis Example 11. Synthesis of Compound 11
중간체 21의 합성Synthesis of Intermediate 21
Figure PCTKR2019006050-appb-I000062
Figure PCTKR2019006050-appb-I000062
중간체 1의 합성에서 화합물 B-1 대신 화합물 B-6 10 g을 사용한 것을 제외하고 중간체 1의 합성법과 동일한 방법으로 중간체 21 7.5 g을 수득하였다. (수율 55 %, Mass [M+]=407) 7.5 g of intermediate 21 was obtained by the same method as the synthesis of intermediate 1, except that 10 g of compound B-6 was used instead of compound B-1 in the synthesis of intermediate 1. (Yield 55%, Mass [M + ] = 407)
중간체 22의 합성Synthesis of Intermediate 22
Figure PCTKR2019006050-appb-I000063
Figure PCTKR2019006050-appb-I000063
중간체 2의 합성에서 중간체 1 대신 중간체 21 7 g을 사용한 것을 제외하고 중간체 2의 합성법과 동일한 방법으로 중간체 22 4.8 g을 수득하였다. (수율 74 %, Mass [M+]=379)4.8 g of intermediate 22 was obtained by the same method as the synthesis of intermediate 2, except that 7 g of intermediate 21 was used instead of intermediate 1 in the synthesis of intermediate 2. (Yield 74%, Mass [M + ] = 379)
중간체 24의 합성Synthesis of Intermediate 24
Figure PCTKR2019006050-appb-I000064
Figure PCTKR2019006050-appb-I000064
중간체 4의 합성에서 중간체 2 대신 중간체 22 4.5 g을 사용한 것을 제외하고 중간체 4의 합성법과 동일한 방법으로 중간체 24 4.3 g을 수득하였다. (수율 56 %, Mass [M+]=641)4.3 g of intermediate 24 was obtained by the same method as the synthesis of intermediate 4, except that 4.5 g of intermediate 22 was used instead of intermediate 2 in the synthesis of intermediate 4. (Yield 56%, Mass [M + ] = 641)
화합물 11의 합성Synthesis of Compound 11
Figure PCTKR2019006050-appb-I000065
Figure PCTKR2019006050-appb-I000065
화합물 1의 합성에서 중간체 4 대신 중간체 24 2.3을 사용하고, 화합물 a-1 대신 화합물 a-11 1.4 g을 사용한 것을 제외하고 화합물 1의 합성법과 동일한 방법으로 화합물 11 1.8 g을 수득하였다. (수율 76 %, Mass [M+]=681)1.8 g of Compound 11 was obtained by the same method as the synthesis of Compound 1, except that Intermediate 24 2.3 was used instead of Intermediate 4 and 1.4 g of Compound a-11 instead of Compound a-1. (Yield 76%, Mass [M + ] = 681)
합성예 12. 화합물 12의 합성Synthesis Example 12 Synthesis of Compound 12
Figure PCTKR2019006050-appb-I000066
Figure PCTKR2019006050-appb-I000066
화합물 1의 합성에서 중간체 4 대신 중간체 24 2 g을 사용하고, 화합물 a-1 대신 화합물 a-12 1.1 g을 사용한 것을 제외하고, 화합물 1의 합성법과 동일한 방법으로 화합물 12 1.4g을 수득하였다. (수율 68 %, Mass [M+]=663)1.4 g of Compound 12 was obtained by the same method as the synthesis of Compound 1, except that 2 g of Intermediate 24 was used instead of Intermediate 4 in the synthesis of Compound 1, and 1.1 g of Compound a-12 was used instead of Compound a-1. (Yield 68%, Mass [M + ] = 663)
합성예 13. 화합물 13의 합성Synthesis Example 13 Synthesis of Compound 13
중간체 25의 합성Synthesis of Intermediate 25
Figure PCTKR2019006050-appb-I000067
Figure PCTKR2019006050-appb-I000067
중간체 1의 합성에서 화합물 A-1 대신 화합물 A-2 8 g을 사용하고, 화합물 B-1 대신 화합물 B-7 10 g을 사용한 것을 제외하고 중간체 1의 합성법과 동일한 방법으로 중간체 25 6.5 g을 수득하였다. (수율 50 %, Mass [M+]=457)In the synthesis of Intermediate 1, 6.5 g of Intermediate 25 was obtained by the same method as the synthesis of Intermediate 1, except that 8 g of Compound A-2 was used instead of Compound A-1 and 10 g of Compound B-7 was used instead of Compound B-1. It was. (Yield 50%, Mass [M + ] = 457)
중간체 26의 합성Synthesis of Intermediate 26
Figure PCTKR2019006050-appb-I000068
Figure PCTKR2019006050-appb-I000068
중간체 2의 합성에서 중간체 1 대신 중간체 25 6 g을 사용한 것을 제외하고 중간체 2의 합성법과 동일한 방법으로 중간체 26 4.2 g을 수득하였다. (수율 75 %, Mass [M+]=429)4.2 g of intermediate 26 was obtained by the same method as the synthesis of intermediate 2, except that 6 g of intermediate 25 was used instead of intermediate 1 in the synthesis of intermediate 2. (Yield 75%, Mass [M + ] = 429)
중간체 28의 합성Synthesis of Intermediate 28
Figure PCTKR2019006050-appb-I000069
Figure PCTKR2019006050-appb-I000069
중간체 4의 합성에서 중간체 2 대신 중간체 26 4 g을 사용한 것을 제외하고 중간체 4의 합성법과 동일한 방법으로 중간체 28 3.8 g을 수득하였다. (수율 59 %, Mass [M+]=691)3.8 g of intermediate 28 was obtained by the same method as the synthesis of intermediate 4, except that 4g of intermediate 26 was used instead of intermediate 2 in the synthesis of intermediate 4. (Yield 59%, Mass [M + ] = 691)
화합물 13의 합성Synthesis of Compound 13
Figure PCTKR2019006050-appb-I000070
Figure PCTKR2019006050-appb-I000070
화합물 1의 합성에서 중간체 4 대신 중간체 28 2 g을 사용하고, 화합물 a-1 대신 화합물 a-13 2 g을 사용한 것을 제외하고 화합물 1의 합성법과 동일한 방법으로 화합물 13 1.6 g을 수득하였다. (수율 53 %, Mass [M+]=1046)1.6 g of Compound 13 was obtained by the same method as the synthesis of Compound 1, except that 2 g of Intermediate 28 was used instead of Intermediate 4 in the synthesis of Compound 1, and 2 g of Compound a-13 was used instead of Compound a-1. (Yield 53%, Mass [M + ] = 1046)
합성예 14. 화합물 14의 합성Synthesis Example 14 Synthesis of Compound 14
Figure PCTKR2019006050-appb-I000071
Figure PCTKR2019006050-appb-I000071
화합물 1의 합성에서 중간체 4 대신 중간체 28 1.8 g을 사용하고, 화합물 a-1 대신 화합물 a-14 1.8 g을 사용한 것을 제외하고 화합물 1의 합성법과 동일한 방법으로 화합물 14 1.4 g을 수득하였다. (수율 51 %, Mass [M+]=1046)1.4 g of Compound 14 was obtained by the same method as the synthesis of Compound 1, except that 1.8 g of Intermediate 28 was used instead of Intermediate 4 in the synthesis of Compound 1, and 1.8 g of Compound a-14 was used instead of Compound a-1. (Yield 51%, Mass [M + ] = 1046)
합성예 15. 화합물 15의 합성Synthesis Example 15 Synthesis of Compound 15
중간체 29의 합성Synthesis of Intermediate 29
Figure PCTKR2019006050-appb-I000072
Figure PCTKR2019006050-appb-I000072
중간체 1의 합성에서 화합물 A-1 대신 화합물 A-4 8 g을 사용하고, 화합물 B-1 대신 화합물 B-8 10 g을 사용한 것을 제외하고 중간체 1의 합성법과 동일한 방법으로 중간체 29 7.1 g을 수득하였다. (수율 54 %, Mass [M+]=457)7.1 g of intermediate 29 was obtained by the same method as the synthesis of Intermediate 1, except that 8 g of Compound A-4 was used instead of Compound A-1 and 10 g of Compound B-8 instead of Compound B-1 in the synthesis of Intermediate 1. It was. (Yield 54%, Mass [M + ] = 457)
중간체 30의 합성Synthesis of Intermediate 30
Figure PCTKR2019006050-appb-I000073
Figure PCTKR2019006050-appb-I000073
중간체 2의 합성에서 중간체 1 대신 중간체 29 6.5 g을 사용한 것을 제외하고 중간체 2의 합성법과 동일한 방법으로 중간체 30 4.2 g을 수득하였다. (수율 69 %, Mass [M+]=429)4.2 g of intermediate 30 was obtained by the same method as the synthesis of intermediate 2, except that 6.5 g of intermediate 29 was used instead of intermediate 1 in the synthesis of intermediate 2. (Yield 69%, Mass [M + ] = 429)
중간체 32의 합성Synthesis of Intermediate 32
Figure PCTKR2019006050-appb-I000074
Figure PCTKR2019006050-appb-I000074
중간체 4의 합성에서 중간체 2 대신 중간체 30 4 g을 사용한 것을 제외하고 중간체 4의 합성법과 동일한 방법으로 중간체 32 4 g을 수득하였다. (수율 62 %, Mass [M+]=691)4 g of Intermediate 32 was obtained by the same method as the synthesis of Intermediate 4, except that 4 g of Intermediate 30 was used instead of Intermediate 2 in the synthesis of Intermediate 4. (Yield 62%, Mass [M + ] = 691)
화합물 15의 합성Synthesis of Compound 15
Figure PCTKR2019006050-appb-I000075
Figure PCTKR2019006050-appb-I000075
화합물 1의 합성에서 중간체 4 대신 중간체 32 3 g을 사용하고, 화합물 a-1 대신 화합물 a-15 2 g을 사용한 것을 제외하고 화합물 1의 합성법과 동일한 방법으로 화합물 15 2 g을 수득하였다. (수율 56 %, Mass [M+]=818) Compound 1 2 g was obtained in the same manner as in the synthesis of Compound 1, except that 3 g of Intermediate 32 was used instead of Intermediate 4 in the synthesis of Compound 1, and 2 g of Compound a-15 was used instead of Compound a-1. (Yield 56%, Mass [M + ] = 818)
합성예 16. 화합물 16의 합성Synthesis Example 16 Synthesis of Compound 16
Figure PCTKR2019006050-appb-I000076
Figure PCTKR2019006050-appb-I000076
화합물 1의 합성에서 중간체 4 대신 중간체 32 1.8 g을 사용하고, 화합물 a-1 대신 화합물 a-16 1.2 g을 이용하여 화합물 1의 합성법과 동일한 방법으로 화합물 16 0.8 g을 수득하였다. (수율 69 %, Mass [M+]=806)0.8 g of Compound 16 was obtained by the same method as the synthesis of Compound 1, using 1.8 g of Intermediate 32 instead of Intermediate 4 and 1.2 g of Compound a-16 instead of Compound a-1. (Yield 69%, Mass [M + ] = 806)
합성예 17. 화합물 17의 합성Synthesis Example 17 Synthesis of Compound 17
중간체 33의 합성Synthesis of Intermediate 33
Figure PCTKR2019006050-appb-I000077
Figure PCTKR2019006050-appb-I000077
중간체 1의 합성에서 화합물 A-1 대신 화합물 A-4 9.3 g을 사용하고, 화합물 B-1 대신 화합물 B-9 10 g을 사용한 것을 제외하고 중간체 1의 합성법과 동일한 방법으로 중간체 33 6.6 g을 수득하였다. (수율 49 %, Mass [M+]=407)6.6 g of intermediate 33 was obtained by the same method as the synthesis of intermediate 1, except that 9.3 g of compound A-4 was used instead of compound A-1 and 10 g of compound B-9 was used instead of compound B-1 in the synthesis of intermediate 1. It was. (Yield 49%, Mass [M + ] = 407)
중간체 34의 합성Synthesis of Intermediate 34
Figure PCTKR2019006050-appb-I000078
Figure PCTKR2019006050-appb-I000078
중간체 2의 합성에서 중간체 1 대신 중간체 33 6 g을 사용한 것을 제외하고 중간체 2의 합성법과 동일한 방법으로 중간체 34 4.2 g을 수득하였다. (수율 75 %, Mass [M+]=379)4.2 g of intermediate 34 was obtained by the same method as the synthesis of intermediate 2, except that 6 g of intermediate 33 was used instead of intermediate 1 in the synthesis of intermediate 2. (Yield 75%, Mass [M + ] = 379)
중간체 36의 합성Synthesis of Intermediate 36
Figure PCTKR2019006050-appb-I000079
Figure PCTKR2019006050-appb-I000079
중간체 4의 합성에서 중간체 2 대신 중간체 34 4 g을 사용한 것을 제외하고 중간체 4의 합성법과 동일한 방법으로 중간체 36 3.8 g을 수득하였다. (수율 56 %, Mass [M+]=641)3.8 g of intermediate 36 was obtained by the same method as the synthesis of intermediate 4, except that 4 g of Intermediate 34 was used instead of Intermediate 2 in the synthesis of Intermediate 4. (Yield 56%, Mass [M + ] = 641)
화합물 17의 합성Synthesis of Compound 17
Figure PCTKR2019006050-appb-I000080
Figure PCTKR2019006050-appb-I000080
화합물 1의 합성에서 중간체 4 대신 중간체 36 3 g을 사용하고, 화합물 a-1 대신 화합물 a-17 3.2 g을 사용한 것을 제외하고 화합물 1의 합성법과 동일한 방법으로 화합물 17 2.6 g을 수득하였다. (수율 56 %, Mass [M+]=988)2.6 g of Compound 17 was obtained by the same method as the synthesis of Compound 1, except that 3 g of Intermediate 36 was used instead of Intermediate 4 in the synthesis of Compound 1, and 3.2 g of Compound a-17 was used instead of Compound a-1. (Yield 56%, Mass [M + ] = 988)
합성예 18. 화합물 18의 합성Synthesis Example 18 Synthesis of Compound 18
Figure PCTKR2019006050-appb-I000081
Figure PCTKR2019006050-appb-I000081
화합물 1의 합성에서 중간체 4 대신 중간체 36 0.8 g을 사용하고, 화합물 a-1 대신 화합물 a-18 0.6 g을 이용하여 화합물 1의 합성법과 동일하게 제조하여 화합물 18 0.6 g을 수득하였다. (수율 68%, Mass [M+]=812)Synthesis of Compound 1 was carried out in the same manner as in the synthesis of Compound 1, using 0.8 g of Intermediate 36 instead of Intermediate 4 and 0.6 g of Compound a-18 instead of Compound a-1 to obtain 0.6 g of Compound 18. (Yield 68%, Mass [M + ] = 812)
합성예 19. 화합물 19의 합성Synthesis Example 19 Synthesis of Compound 19
중간체 37의 합성Synthesis of Intermediate 37
Figure PCTKR2019006050-appb-I000082
Figure PCTKR2019006050-appb-I000082
중간체 1의 합성에서 화합물 A-1 대신 화합물 A-2 8 g을 사용하고, 화합물 B-1 대신 화합물 B-10 10 g을 사용한 것을 제외하고 중간체 1의 합성법과 동일한 방법으로 중간체 37 7.5 g을 수득하였다. (수율 57 %, Mass [M+]=407)7.5 g of intermediate 37 was obtained by the same method as the synthesis of intermediate 1, except that 8 g of compound A-2 was used instead of compound A-1 in the synthesis of intermediate 1, and 10 g of compound B-10 was used instead of compound B-1. It was. (Yield 57%, Mass [M + ] = 407)
중간체 38의 합성Synthesis of Intermediate 38
Figure PCTKR2019006050-appb-I000083
Figure PCTKR2019006050-appb-I000083
중간체 2의 합성에서 중간체 1 대신 중간체 37 7 g을 사용한 것을 제외하고 중간체 2의 합성법과 동일한 방법으로 중간체 38 4.6 g을 수득하였다. (수율 70 %, Mass [M+]=379)4.6 g of Intermediate 38 was obtained by the same method as the synthesis of Intermediate 2, except that 7 g of Intermediate 37 was used instead of Intermediate 1 in the synthesis of Intermediate 2. (Yield 70%, Mass [M + ] = 379)
중간체 40의 합성Synthesis of Intermediate 40
Figure PCTKR2019006050-appb-I000084
Figure PCTKR2019006050-appb-I000084
중간체 4의 합성에서 중간체 2 대신 중간체 38 4 g을 사용한 것을 제외하고 중간체 4의 합성법과 동일한 방법으로 중간체 40 3.6 g을 수득하였다. (수율 56 %, Mass [M+]=641)3.6 g of intermediate 40 was obtained by the same method as the synthesis of intermediate 4, except that 4 g of intermediate 38 was used instead of intermediate 2 in the synthesis of intermediate 4. (Yield 56%, Mass [M + ] = 641)
화합물 19의 합성Synthesis of Compound 19
Figure PCTKR2019006050-appb-I000085
Figure PCTKR2019006050-appb-I000085
화합물 1의 합성에서 중간체 4 대신 중간체 40 2 g을 사용하고, 화합물 a-1 대신 화합물 a-19 1.3 g을 사용한 것을 제외하고 화합물 1의 합성법과 동일한 방법으로 화합물 19 1.4 g을 수득하였다. (수율 61 %, Mass [M+]=795)1.4 g of Compound 19 was obtained by the same method as the synthesis of Compound 1, except that 2 g of Intermediate 40 was used instead of Intermediate 4 in the synthesis of Compound 1, and 1.3 g of Compound a-19 was used instead of Compound a-1. (Yield 61%, Mass [M + ] = 795)
합성예 20. 화합물 20의 합성Synthesis Example 20 Synthesis of Compound 20
Figure PCTKR2019006050-appb-I000086
Figure PCTKR2019006050-appb-I000086
화합물 1의 합성에서 중간체 4 대신 중간체 40 1.7 g을 사용하고, 화합물 a-1 대신 화합물 a-20 1.5 g을 이용하여 화합물 1의 합성법과 동일한 방법으로 화합물 20 1.5 g을 수득하였다. (수율 66 %, Mass [M+]=982)1.5 g of compound 20 was obtained by the same method as the synthesis method of compound 1, using 1.7 g of Intermediate 40 instead of Intermediate 4 and 1.5 g of Compound a-20 instead of Compound a-1. (Yield 66%, Mass [M + ] = 982)
합성예 21. 화합물 21의 합성Synthesis Example 21 Synthesis of Compound 21
중간체 41의 합성Synthesis of Intermediate 41
Figure PCTKR2019006050-appb-I000087
Figure PCTKR2019006050-appb-I000087
중간체 1의 합성에서 화합물 A-1 대신 화합물 A-5 3.8 g을 사용하고, 화합물 B-1 대신 화합물 B-11 5 g을 사용한 것을 제외하고 중간체 1의 합성법과 동일한 방법으로 중간체 41 4.2 g을 수득하였다. (수율 65 %, Mass [M+]=473)4.2 g of intermediate 41 was obtained by the same method as the synthesis of intermediate 1, except that 3.8 g of compound A-5 was used instead of compound A-1 and 5 g of compound B-11 instead of compound B-1 in the synthesis of intermediate 1. It was. (Yield 65%, Mass [M + ] = 473)
중간체 42의 합성Synthesis of Intermediate 42
Figure PCTKR2019006050-appb-I000088
Figure PCTKR2019006050-appb-I000088
중간체 2의 합성에서 중간체 1 대신 중간체 41 4 g을 사용한 것을 제외하고 중간체 2의 합성법과 동일한 방법으로 중간체 42 2.8 g을 수득하였다. (수율 74 %, Mass [M+]=445)2.8 g of Intermediate 42 was obtained by the same method as the synthesis of Intermediate 2, except that 4 g of Intermediate 41 was used instead of Intermediate 1 in the synthesis of Intermediate 2. (Yield 74%, Mass [M + ] = 445)
중간체 44의 합성Synthesis of Intermediate 44
Figure PCTKR2019006050-appb-I000089
Figure PCTKR2019006050-appb-I000089
중간체 4의 합성에서 중간체 2 대신 중간체 42 2.5 g을 사용한 것을 제외하고 중간체 4의 합성법과 동일한 방법으로 중간체 44 2.4 g을 수득하였다. (수율 60 %, Mass [M+]=707)2.4 g of intermediate 44 was obtained by the same method as the synthesis of intermediate 4, except that 2.5 g of intermediate 42 was used instead of intermediate 2 in the synthesis of intermediate 4. (Yield 60%, Mass [M + ] = 707)
화합물 21의 합성Synthesis of Compound 21
Figure PCTKR2019006050-appb-I000090
Figure PCTKR2019006050-appb-I000090
화합물 1의 합성에서 중간체 4 대신 중간체 44 1.2g을 사용하고, 화합물 a-1 대신 화합물 a-21 1.3 g을 사용한 것을 제외하고 화합물 1의 합성법과 동일한 방법으로 화합물 21 1 g을 수득하였다. (수율 52 %, Mass [M+]=1142) Compound 1 1 g was obtained in the same manner as in the synthesis of Compound 1, except that 1.2 g of Intermediate 44 was used instead of Intermediate 4 and 1.3 g of Compound a-21 was used instead of Compound a-1. (Yield 52%, Mass [M + ] = 1142)
합성예 22. 화합물 22의 합성Synthesis Example 22 Synthesis of Compound 22
Figure PCTKR2019006050-appb-I000091
Figure PCTKR2019006050-appb-I000091
화합물 1의 합성에서 중간체 4 대신 중간체 44 1.2 g을 사용하고, 화합물 a-1 대신 화합물 a-22를 사용한 것을 제외하고 화합물 1의 합성법과 동일한 방법으로 화합물 22 1.1 g을 수득하였다. (수율 62 %, Mass [M+]=457)1.1 g of Compound 22 was obtained by the same method as the synthesis of Compound 1, except that 1.2 g of Intermediate 44 was used instead of Intermediate 4 in the synthesis of Compound 1, and Compound a-22 was used instead of Compound a-1. (Yield 62%, Mass [M + ] = 457)
합성예 23. 화합물 23의 합성Synthesis Example 23 Synthesis of Compound 23
중간체 45의 합성Synthesis of Intermediate 45
Figure PCTKR2019006050-appb-I000092
Figure PCTKR2019006050-appb-I000092
중간체 1의 합성에서 화합물 B-1 대신 화합물 B-12 5 g을 사용한 것을 제외하고 중간체 1의 합성법과 동일한 방법으로 중간체 45 3.8 g을 수득하였다. (수율 59 %, Mass [M+]=473) 3.8 g of intermediate 45 was obtained by the same method as the synthesis of intermediate 1, except that 5 g of compound B-12 was used instead of compound B-1 in the synthesis of intermediate 1. (Yield 59%, Mass [M + ] = 473)
중간체 46의 합성Synthesis of Intermediate 46
Figure PCTKR2019006050-appb-I000093
Figure PCTKR2019006050-appb-I000093
중간체 2의 합성에서 중간체 1 대신 중간체 45 3.5 g을 사용한 것을 제외하고 중간체 2의 합성법과 동일한 방법으로 중간체 46 2.6 g을 수득하였다. (수율 79 %, Mass [M+]=445)2.6 g of intermediate 46 was obtained by the same method as the synthesis of intermediate 2, except that 3.5 g of intermediate 45 was used instead of intermediate 1 in the synthesis of intermediate 2. (Yield 79%, Mass [M + ] = 445)
중간체 48의 합성Synthesis of Intermediate 48
Figure PCTKR2019006050-appb-I000094
Figure PCTKR2019006050-appb-I000094
중간체 4의 합성에서 중간체 2 대신 중간체 46 2.5 g을 사용한 것을 제외하고 중간체 4의 합성법과 동일한 방법으로 중간체 48 2.1 g을 수득하였다. (수율 53 %, Mass [M+]=707)2.1 g of intermediate 48 was obtained by the same method as the synthesis of intermediate 4, except that 2.5 g of intermediate 46 was used instead of intermediate 2 in the synthesis of intermediate 4. (Yield 53%, Mass [M + ] = 707)
화합물 23의 합성Synthesis of Compound 23
Figure PCTKR2019006050-appb-I000095
Figure PCTKR2019006050-appb-I000095
화합물 1의 합성에서 중간체 4 대신 중간체 48 1.1 g을 사용하고, 화합물 a-1 대신 화합물 a-23 0.9 g을 사용한 것을 제외하고 화합물 1의 합성법과 동일한 방법으로 화합물 23 0.8 g을 수득하였다. (수율 57 %, Mass [M+]=901)0.8 g of Compound 23 was obtained by the same method as the synthesis of Compound 1, except that 1.1 g of Intermediate 48 was used instead of Intermediate 4 in the synthesis of Compound 1, and 0.9 g of Compound a-23 was used instead of Compound a-1. (Yield 57%, Mass [M + ] = 901)
합성예 24. 화합물 24의 합성Synthesis Example 24 Synthesis of Compound 24
Figure PCTKR2019006050-appb-I000096
Figure PCTKR2019006050-appb-I000096
화합물 1의 합성에서 중간체 4 대신 중간체 48 1.1 g을 사용하고, 화합물 a-1 대신 화합물 a-24 0.6 g을 이용하여 화합물 1의 합성법과 동일한 방법으로 화합물 24 0.7 g을 수득하였다. (수율 64 %, Mass [M+]=778)0.7 g of compound 24 was obtained by the same method as the synthesis method of compound 1, using 1.1 g of Intermediate 48 instead of Intermediate 4 and 0.6 g of Compound a-24 instead of Compound a-1. (Yield 64%, Mass [M + ] = 778)
합성예 25. 화합물 25의 합성Synthesis Example 25 Synthesis of Compound 25
중간체 49의 합성Synthesis of Intermediate 49
Figure PCTKR2019006050-appb-I000097
Figure PCTKR2019006050-appb-I000097
중간체 1의 합성에서 화합물 A-1 대신 화합물 A-2 2.4 g을 사용하고, 화합물 B-1 대신 화합물 B-13 3 g을 사용한 것을 제외하고 중간체 1의 합성법과 동일한 방법으로 중간체 49 2.6 g을 수득하였다. (수율 66 %, Mass [M+]=449)2.6 g of intermediate 49 was obtained by the same method as the synthesis of Intermediate 1, except that 2.4 g of Compound A-2 was used instead of Compound A-1 and 3 g of Compound B-13 was used instead of Compound B-1 in the synthesis of Intermediate 1. It was. (Yield 66%, Mass [M + ] = 449)
중간체 50의 합성Synthesis of Intermediate 50
Figure PCTKR2019006050-appb-I000098
Figure PCTKR2019006050-appb-I000098
중간체 2의 합성에서 중간체 1 대신 중간체 49 2.5 g을 사용한 것을 제외하고 중간체 2의 합성법과 동일한 방법으로 중간체 50 1.7 g을 수득하였다. (수율 73%, Mass [M+]=421)1.7 g of intermediate 50 was obtained by the same method as the synthesis of intermediate 2, except that 2.5 g of Intermediate 49 was used instead of Intermediate 1 in the synthesis of Intermediate 2. (Yield 73%, Mass [M + ] = 421)
중간체 52의 합성Synthesis of Intermediate 52
Figure PCTKR2019006050-appb-I000099
Figure PCTKR2019006050-appb-I000099
중간체 4의 합성에서 중간체 2 대신 중간체 50 1.5 g을 사용한 것을 제외하고 중간체 4의 합성법과 동일한 방법으로 중간체 52 1.4 g을 수득하였다. (수율 58 %, Mass [M+]=684)1.4 g of intermediate 52 was obtained by the same method as the synthesis of intermediate 4, except that 1.5 g of intermediate 50 was used instead of intermediate 2 in the synthesis of intermediate 4. (Yield 58%, Mass [M + ] = 684)
화합물 25의 합성Synthesis of Compound 25
Figure PCTKR2019006050-appb-I000100
Figure PCTKR2019006050-appb-I000100
화합물 1의 합성에서 중간체 4 대신 중간체 52 1.4 g을 사용하고, 화합물 a-1 대신 화합물 a-25 1 g을 사용한 것을 제외하고 화합물 1의 합성법과 동일한 방법으로 화합물 25 1.1 g을 수득하였다. (수율 64 %, Mass [M+]=834)1.1 g of Compound 25 was obtained by the same method as the synthesis of Compound 1, except that 1.4 g of Intermediate 52 was used instead of Intermediate 4 in the synthesis of Compound 1, and 1 g of Compound a-25 was used instead of Compound a-1. (Yield 64%, Mass [M + ] = 834)
합성예 26. 화합물 26의 합성Synthesis Example 26 Synthesis of Compound 26
중간체 53의 합성Synthesis of Intermediate 53
Figure PCTKR2019006050-appb-I000101
Figure PCTKR2019006050-appb-I000101
중간체 1의 합성에서 화합물 A-1 대신 화합물 A-2 1.8 g을 사용하고, 화합물 B-1 대신 화합물 B-14 3 g을 사용한 것을 제외하고 중간체 1의 합성법과 동일한 방법으로 중간체 53 2.7 g을 수득하였다. (수율 73 %, Mass [M+]=562)2.7 g of Intermediate 53 was obtained by the same method as the synthesis of Intermediate 1, except that 1.8 g of Compound A-2 was used instead of Compound A-1 and 3 g of Compound B-14 was used instead of Compound B-1 in the synthesis of Intermediate 1. It was. (Yield 73%, Mass [M + ] = 562)
중간체 54의 합성Synthesis of Intermediate 54
Figure PCTKR2019006050-appb-I000102
Figure PCTKR2019006050-appb-I000102
중간체 2의 합성에서 중간체 1 대신 중간체 53 2.5 g을 사용한 것을 제외하고 중간체 2의 합성법과 동일한 방법으로 중간체 54 1.9 g을 수득하였다. (수율 80 %, Mass [M+]=534)1.9 g of intermediate 54 was obtained by the same method as the synthesis of intermediate 2, except that 2.5 g of Intermediate 53 was used instead of Intermediate 1 in the synthesis of Intermediate 2. (Yield 80%, Mass [M + ] = 534)
중간체 56의 합성Synthesis of Intermediate 56
Figure PCTKR2019006050-appb-I000103
Figure PCTKR2019006050-appb-I000103
중간체 4의 합성에서 중간체 2 대신 중간체 54 1.5 g을 사용한 것을 제외하고 중간체 4의 합성법과 동일한 방법으로 중간체 56 1.2 g을 수득하였다. (수율 54 %, Mass [M+]=796)1.2 g of intermediate 56 was obtained by the same method as the synthesis of intermediate 4, except that 1.5 g of intermediate 54 was used instead of intermediate 2 in the synthesis of intermediate 4. (Yield 54%, Mass [M + ] = 796)
화합물 26의 합성Synthesis of Compound 26
Figure PCTKR2019006050-appb-I000104
Figure PCTKR2019006050-appb-I000104
화합물 1의 합성에서 중간체 4 대신 중간체 56 1.2 g을 사용하고, 화합물 a-1 대신 화합물 a-26 0.8 g을 사용한 것을 제외하고 화합물 1의 합성법과 동일한 방법으로 화합물 26 1 g을 수득하였다. (수율 66 %, Mass [M+]=1010) Compound 1 1 g was obtained in the same manner as in the synthesis of Compound 1, except that 1.2 g of Intermediate 56 was used instead of Intermediate 4 and 0.8 g of Compound a-26 was used instead of Compound a-1. (Yield 66%, Mass [M + ] = 1010)
<실시예 1><Example 1>
ITO가 100 nm 두께로 박막 코팅된 유리 기판(corning 7059 glass)을, 분산제를 녹인 증류수에 넣고 초음파로 세척하였다. 세제는 Fischer Co.의 제품을 사용하였으며, 증류수는 Millipore Co. 제품의 필터(Filter)로 2차 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후, 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후 이소프로필알콜, 아세톤, 메탄올 용제 순서로 초음파 세척을 하고 건조시켰다. A glass substrate (corning 7059 glass) coated with a thin film of ITO at a thickness of 100 nm was placed in distilled water in which a dispersant was dissolved and ultrasonically washed. Fischer Co. was used for the detergent, and Millipore Co. Secondary filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.
이렇게 준비된 ITO 투명 전극 위에 하기 화합물 HAT-CN을 5 nm의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 그 위에 하기 화합물 HT-A을 진공 증착하여 100 nm 두께의 제1 정공수송층을 형성하고, 연이어 하기 화합물 HT-B을 진공 증착하여 10 nm 두께의 제2 정공수송층을 형성하였다. 상기 제2 정공수송층 위에 호스트 화합물 BH-1와 화합물 1을 98:2의 중량비로 진공 증착하여 20 nm 두께의 발광층을 형성하였다. The following compound HAT-CN was thermally vacuum deposited to a thickness of 5 nm on the prepared ITO transparent electrode to form a hole injection layer. The following compound HT-A was vacuum deposited to form a first hole transport layer having a thickness of 100 nm, and the following compound HT-B was subsequently vacuum deposited to form a second hole transport layer having a thickness of 10 nm. The host compound BH-1 and compound 1 were vacuum deposited on the second hole transport layer at a weight ratio of 98: 2 to form a light emitting layer having a thickness of 20 nm.
그 다음에 하기 화합물 ET-A와 화합물 Liq를 1:1 중량비로 증착하여 30 nm의 전자 주입 및 수송층을 형성하였다. 이 위에 은(Ag)과 마그네슘(Mg)을 9:1의 중량비로 15 nm 두께로 증착하고, 알루미늄을 100 nm 두께로 증착하여 음극을 형성하여, 유기 발광 소자를 제조하였다. Then, the following Compound ET-A and Compound Liq were deposited in a 1: 1 weight ratio to form an electron injection and transport layer at 30 nm. Silver (Ag) and magnesium (Mg) were deposited to a thickness of 15 nm in a weight ratio of 9: 1, and aluminum was deposited to a thickness of 100 nm to form a cathode, thereby manufacturing an organic light emitting device.
상기의 과정에서 유기물의 증착속도는 0.1 nm/sec를 유지하였고, 은과 마그네슘의 증착속도는 0.02 nm/sec, 알루미늄의 증착속도는 0.3 nm/sec 내지 0.7 nm/sec의 증착속도를 유지하였다. In the above process, the deposition rate of the organic material was maintained at 0.1 nm / sec, the deposition rate of silver and magnesium was 0.02 nm / sec, and the deposition rate of aluminum was 0.3 nm / sec to 0.7 nm / sec.
Figure PCTKR2019006050-appb-I000105
Figure PCTKR2019006050-appb-I000105
<실시예 2 내지 28><Examples 2 to 28>
상기 실시예 1에서 화합물 1 대신 하기 표 1의 화합물을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 실시예 2 내지 26의 유기 발광 소자를 제작하였다.The organic light emitting device of Examples 2 to 26 was manufactured by the same method as Example 1, except that the compound of Table 1 was used instead of the compound 1 in Example 1.
실시예 27의 유기 발광 소자는 상기 실시예 1에서 발광층에 화합물 BH-1 대신 화합물 BH-2를 사용하고, 화합물 1 대신 화합물 17을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 제작하였다.The organic light emitting device of Example 27 was manufactured in the same manner as in Example 1, except that Compound BH-2 was used for Compound 1 instead of Compound BH-1 and Compound 17 was used instead of Compound 1 in Example 1.
실시예 28의 유기 발광 소자는 상기 실시예 1에서 발광층에 화합물 BH-1 대신 화합물 BH-1과 화합물 BH-2를 1:1의 중량비로 사용하고, 화합물 1 대신 화합물 11을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 제작하였다. The organic light emitting device of Example 28 was used in Example 1, except that Compound BH-1 and Compound BH-2 were used in the light emitting layer instead of Compound BH-1 in a weight ratio of 1: 1, and Compound 11 was used instead of Compound 1. It produced in the same manner as in Example 1.
Figure PCTKR2019006050-appb-I000106
Figure PCTKR2019006050-appb-I000106
Figure PCTKR2019006050-appb-I000107
Figure PCTKR2019006050-appb-I000107
<비교예 1 내지 7><Comparative Examples 1 to 7>
상기 실시예 1에서 화합물 1 대신 하기 표 1의 화합물을 사용한 것을 제외하고는 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound of Table 1 in place of Compound 1 in Example 1.
Figure PCTKR2019006050-appb-I000108
Figure PCTKR2019006050-appb-I000108
상기 실시예 및 비교예의 유기 발광 소자에 10 mA/cm2의 전류 밀도를 인가할 때의 전압, 효율, 발광색(CIE 색좌표) 및 20 mA/cm2의 전류 밀도를 인가할 때의 수명(T95)을 측정하고, 그 결과를 하기 표 1에 나타내었다. 이 때, T95는 전류 밀도 20 mA/cm2에서의 초기 휘도를 100%로 하였을 때 휘도가 95%로 감소되는데 소요되는 시간을 의미한다.10 mA / cm 2 of the organic light emitting device of Examples and Comparative Examples Voltage, efficiency, emission color (CIE color coordinate) and 20 mA / cm 2 when current density is applied. The lifetime (T 95 ) at the time of applying the current density was measured, and the results are shown in Table 1 below. At this time, T 95 means the time required to reduce the luminance to 95% when the initial luminance at the current density of 20 mA / cm 2 is 100%.
구분division 호스트Host 도판트 화합물Dopant compound 구동전압(V)Driving voltage (V) 효율(cd/A)Efficiency (cd / A) 색좌표CIE(y)Color coordinates CIE (y) T95(hr)T 95 (hr)
실시예 1 Example 1 BH-1BH-1 1One 4.224.22 7.367.36 0.110.11 130130
실시예 2 Example 2 BH-1BH-1 22 4.204.20 7.377.37 0.110.11 115115
실시예 3 Example 3 BH-1BH-1 33 4.304.30 7.347.34 0.110.11 125125
실시예 4 Example 4 BH-1BH-1 44 4.324.32 7.337.33 0.120.12 135135
실시예 5 Example 5 BH-1BH-1 55 4.234.23 7.337.33 0.100.10 105105
실시예 6 Example 6 BH-1BH-1 66 4.254.25 7.317.31 0.100.10 120120
실시예 7 Example 7 BH-1BH-1 77 4.344.34 7.307.30 0.110.11 124124
실시예 8 Example 8 BH-1BH-1 88 4.404.40 7.437.43 0.100.10 133133
실시예 9 Example 9 BH-1BH-1 99 4.314.31 7.357.35 0.110.11 105105
실시예 10 Example 10 BH-1BH-1 1010 4.324.32 7.307.30 0.100.10 126126
실시예 11 Example 11 BH-1BH-1 1111 4.324.32 7.427.42 0.120.12 138138
실시예 12 Example 12 BH-1BH-1 1212 4.354.35 7.367.36 0.120.12 145145
실시예 13 Example 13 BH-1BH-1 1313 4.334.33 7.377.37 0.120.12 120120
실시예 14 Example 14 BH-1BH-1 1414 4.334.33 7.347.34 0.120.12 115115
실시예 15 Example 15 BH-1BH-1 1515 4.284.28 7.337.33 0.120.12 105105
실시예 16 Example 16 BH-1BH-1 1616 4.264.26 7.287.28 0.120.12 120120
실시예 17 Example 17 BH-1BH-1 1717 4.234.23 7.547.54 0.110.11 125125
실시예 18 Example 18 BH-1BH-1 1818 4.234.23 7.487.48 0.110.11 125125
실시예 19 Example 19 BH-1BH-1 1919 4.364.36 6.846.84 0.130.13 112112
실시예 20Example 20 BH-1BH-1 2020 4.324.32 6.236.23 0.110.11 108108
실시예 21Example 21 BH-1BH-1 2121 4.384.38 5.855.85 0.100.10 118118
실시예 22Example 22 BH-1BH-1 2222 4.364.36 5.805.80 0.110.11 108108
실시예 23Example 23 BH-1BH-1 2323 4.364.36 5.655.65 0.090.09 108108
실시예 24Example 24 BH-1BH-1 2424 4.304.30 5.315.31 0.100.10 112112
실시예 25Example 25 BH-1BH-1 2525 4.384.38 5.355.35 0.110.11 103103
실시예 26Example 26 BH-1BH-1 2626 4.354.35 5.365.36 0.100.10 105105
실시예27Example 27 BH-2BH-2 1717 4.254.25 6.866.86 0.110.11 128128
실시예28Example 28 BH1+BH-2BH1 + BH-2 1111 4.314.31 6.606.60 0.110.11 130130
비교예 1 Comparative Example 1 BH-1BH-1 D1D1 4.404.40 3.113.11 0.180.18 8585
비교예 2 Comparative Example 2 BH-1BH-1 D2D2 4.384.38 2.452.45 0.250.25 7373
비교예 3 Comparative Example 3 BH-1BH-1 D3D3 4.414.41 2.222.22 0.230.23 7272
비교예 4Comparative Example 4 BH-1BH-1 D4D4 4.414.41 3.353.35 0.160.16 8282
비교예 5Comparative Example 5 BH-1BH-1 D5D5 4.524.52 2.282.28 0.210.21 6565
비교예 6Comparative Example 6 BH-1BH-1 D6D6 4.404.40 2.202.20 0.160.16 7070
비교예 7Comparative Example 7 BH-1BH-1 D7D7 4.404.40 2.352.35 0.230.23 8484
상기 표 1에 기재된 바와 같이, 본 발명에 따른 화학식 1로 표시되는 화합물은 유기 발광 소자의 청색 발광층에 사용될 수 있으며, 이를 발광층의 도판트로서 포함하는 실시예 1 내지 28의 유기발광 소자는 본 명세서의 화학식 1 의 코어에 알킬기 및/또는 아릴기를 포함하는 비교예 5 및 6의 유기발광 소자와 화학식 1의 아민 치환기 위치가 상이한 비교예 3 및 4의 유기발광 소자보다 구동전압이 낮고, 효율이 우수하며 장수명의 성능을 가지는 것을 확인할 수 있었다.As shown in Table 1, the compound represented by Formula 1 according to the present invention can be used in the blue light emitting layer of the organic light emitting device, the organic light emitting device of Examples 1 to 28 including this as a dopant of the light emitting layer The organic light emitting diodes of Comparative Examples 5 and 6, which include an alkyl group and / or an aryl group in the core of Chemical Formula 1, and the driving voltage is lower than that of the organic light emitting diodes of Comparative Examples 3 and 4, which differ in the position of the amine substituent of Chemical Formula 1, and the efficiency is excellent. It was confirmed that it has a long life performance.

Claims (14)

  1. 하기 화학식 1로 표시되는 것인 화합물:Compound represented by the following formula (1):
    [화학식 1][Formula 1]
    Figure PCTKR2019006050-appb-I000109
    Figure PCTKR2019006050-appb-I000109
    상기 화학식 1에 있어서,In Chemical Formula 1,
    X는 O, S 또는 Si(R1)(R2)이고,X is O, S or Si (R1) (R2),
    R1 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 수소, 알킬기 또는 아릴기이며,R1 and R2 are the same as or different from each other, and each independently hydrogen, an alkyl group or an aryl group,
    Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 사이클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며, Ar1 to Ar4 are the same as or different from each other, and each independently a substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    상기 '치환 또는 비치환'에서의 치환기는 중수소; 할로겐기; 중수소로 치환 또는 비치환된 사슬형 알킬기; 중수소로 치환 또는 비치환된 사이클로알킬기; 할로알킬기; 알킬기 또는 아릴기로 치환 또는 비치환된 실릴기; 중수소로 치환 또는 비치환된 아릴기; 또는 중수소로 치환 또는 비치환된 헤테로아릴기이며,The substituent in the "substituted or unsubstituted" is deuterium; Halogen group; A chain alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group unsubstituted or substituted with deuterium; Haloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An aryl group unsubstituted or substituted with deuterium; Or a heteroaryl group unsubstituted or substituted with deuterium,
    m은 0 또는 1이다.m is 0 or 1;
  2. 청구항 1에 있어서, 상기 Ar1 내지 Ar4는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 사이클로헥실기; 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 티오페닐기; 치환 또는 비치환된 디벤조퓨라닐기; 치환 또는 비치환된 디벤조티오페닐기; 치환 또는 비치환된 카바졸릴기; 치환 또는 비치환된 나프토벤조퓨라닐기; 치환 또는 비치환된 나프토벤조티오페닐기; 치환 또는 비치환된 피리디닐기; 또는 치환 또는 비치환된 퀴놀리닐기이며,The method according to claim 1, Ar1 to Ar4 are the same as or different from each other, each independently represent a substituted or unsubstituted cyclohexyl group; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted thiophenyl group; Substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophenyl group; Substituted or unsubstituted carbazolyl group; A substituted or unsubstituted naphthobenzofuranyl group; A substituted or unsubstituted naphthobenzothiophenyl group; Substituted or unsubstituted pyridinyl group; Or a substituted or unsubstituted quinolinyl group,
    상기 '치환 또는 비치환'에서의 치환기는 중수소; 할로겐기; 중수소로 치환 또는 비치환된 사슬형 알킬기; 중수소로 치환 또는 비치환된 사이클로알킬기; 할로알킬기; 알킬기 또는 아릴기로 치환 또는 비치환된 실릴기; 중수소로 치환 또는 비치환된 아릴기; 또는 중수소로 치환 또는 비치환된 헤테로아릴기인 것인 화합물.The substituent in the "substituted or unsubstituted" is deuterium; Halogen group; A chain alkyl group unsubstituted or substituted with deuterium; A cycloalkyl group unsubstituted or substituted with deuterium; Haloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; An aryl group unsubstituted or substituted with deuterium; Or a heteroaryl group unsubstituted or substituted with deuterium.
  3. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 1-1 내지 화학식 1-3 중 어느 하나로 표시되는 것인 화합물:The compound of claim 1, wherein Formula 1 is represented by any one of Formulas 1-1 to 1-3:
    [화학식 1-1][Formula 1-1]
    Figure PCTKR2019006050-appb-I000110
    Figure PCTKR2019006050-appb-I000110
    [화학식 1-2][Formula 1-2]
    Figure PCTKR2019006050-appb-I000111
    Figure PCTKR2019006050-appb-I000111
    [화학식 1-3][Formula 1-3]
    Figure PCTKR2019006050-appb-I000112
    Figure PCTKR2019006050-appb-I000112
    상기 화학식 1-1 내지 화학식 1-3에 있어서,In Chemical Formulas 1-1 to 1-3,
    X1 및 X2 중 어느 하나는 직접결합이고, 나머지는 하나는 X이며,One of X1 and X2 is a direct bond, the other is X,
    X, Ar1 내지 Ar4 및 m의 정의는 화학식 1에서 정의한 바와 동일하다.The definitions of X, Ar1 to Ar4 and m are the same as defined in the formula (1).
  4. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 2-1 내지 화학식 2-4 중 어느 하나로 표시되는 것인 화합물:The compound according to claim 1, wherein Formula 1 is represented by any one of Formulas 2-1 to 2-4:
    [화학식 2-1][Formula 2-1]
    Figure PCTKR2019006050-appb-I000113
    Figure PCTKR2019006050-appb-I000113
    [화학식 2-2][Formula 2-2]
    Figure PCTKR2019006050-appb-I000114
    Figure PCTKR2019006050-appb-I000114
    [화학식 2-3][Formula 2-3]
    Figure PCTKR2019006050-appb-I000115
    Figure PCTKR2019006050-appb-I000115
    [화학식 2-4][Formula 2-4]
    Figure PCTKR2019006050-appb-I000116
    Figure PCTKR2019006050-appb-I000116
    상기 화학식 2-1 내지 화학식 2-4에 있어서,In Chemical Formulas 2-1 to 2-4,
    X 및 Ar1 내지 Ar4의 정의는 화학식 1에서 정의한 바와 동일하다.The definitions of X and Ar1 to Ar4 are the same as defined in the formula (1).
  5. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 3-1 내지 화학식 3-4 중 어느 하나로 표시되는 것인 화합물:The compound according to claim 1, wherein Formula 1 is represented by any one of Formulas 3-1 to 3-4:
    [화학식 3-1][Formula 3-1]
    Figure PCTKR2019006050-appb-I000117
    Figure PCTKR2019006050-appb-I000117
    [화학식 3-2][Formula 3-2]
    Figure PCTKR2019006050-appb-I000118
    Figure PCTKR2019006050-appb-I000118
    [화학식 3-3][Formula 3-3]
    Figure PCTKR2019006050-appb-I000119
    Figure PCTKR2019006050-appb-I000119
    [화학식 3-4][Formula 3-4]
    Figure PCTKR2019006050-appb-I000120
    Figure PCTKR2019006050-appb-I000120
    상기 화학식 3-1 내지 화학식 3-4에 있어서,In Chemical Formulas 3-1 to 3-4,
    X, Ar1 내지 Ar4 및 m의 정의는 화학식 1에서 정의한 바와 동일하다.The definitions of X, Ar1 to Ar4 and m are the same as defined in the formula (1).
  6. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 4-1 내지 화학식 4-6 중 어느 하나로 표시되는 것인 화합물:The compound according to claim 1, wherein Formula 1 is represented by any one of Formulas 4-1 to 4-6:
    [화학식 4-1][Formula 4-1]
    Figure PCTKR2019006050-appb-I000121
    Figure PCTKR2019006050-appb-I000121
    [화학식 4-2][Formula 4-2]
    Figure PCTKR2019006050-appb-I000122
    Figure PCTKR2019006050-appb-I000122
    [화학식 4-3][Formula 4-3]
    Figure PCTKR2019006050-appb-I000123
    Figure PCTKR2019006050-appb-I000123
    [화학식 4-4][Formula 4-4]
    Figure PCTKR2019006050-appb-I000124
    Figure PCTKR2019006050-appb-I000124
    [화학식 4-5][Formula 4-5]
    Figure PCTKR2019006050-appb-I000125
    Figure PCTKR2019006050-appb-I000125
    [화학식 4-6][Formula 4-6]
    Figure PCTKR2019006050-appb-I000126
    Figure PCTKR2019006050-appb-I000126
    상기 화학식 4-1 내지 화학식 4-6에 있어서,In Chemical Formulas 4-1 to 4-6,
    X, Ar1 내지 Ar4 및 m의 정의는 화학식 1에서 정의한 바와 동일하다.The definitions of X, Ar1 to Ar4 and m are the same as defined in the formula (1).
  7. 청구항 1에 있어서, 상기 화학식 1로 표시되는 화합물은 하기 화합물들 중에서 선택된 어느 하나인 것인 화합물:The compound of claim 1, wherein the compound represented by Formula 1 is any one selected from the following compounds:
    Figure PCTKR2019006050-appb-I000127
    Figure PCTKR2019006050-appb-I000127
    Figure PCTKR2019006050-appb-I000128
    Figure PCTKR2019006050-appb-I000128
    Figure PCTKR2019006050-appb-I000129
    Figure PCTKR2019006050-appb-I000129
    Figure PCTKR2019006050-appb-I000130
    Figure PCTKR2019006050-appb-I000130
    Figure PCTKR2019006050-appb-I000131
    Figure PCTKR2019006050-appb-I000131
    Figure PCTKR2019006050-appb-I000132
    .
    Figure PCTKR2019006050-appb-I000132
    .
  8. 제1 전극; 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자에 있어서, 상기 유기물층은 청구항 1 내지 7 중 어느 하나의 항에 따른 화학식 1로 표시되는 화합물을 포함하는 것인 유기 발광 소자.A first electrode; Second electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein the organic material layer comprises a compound represented by Chemical Formula 1 according to any one of claims 1 to 7. The organic light emitting device.
  9. 청구항 8에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 발광 소자.The organic light emitting device of claim 8, wherein the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
  10. 청구항 9에 있어서, 상기 발광층은 청색 발광층인 것인 유기 발광 소자.The organic light emitting device of claim 9, wherein the light emitting layer is a blue light emitting layer.
  11. 청구항 9에 있어서, 상기 발광층은 하기 화학식 H로 표시되는 화합물을 더 포함하는 것인 유기 발광 소자:The organic light emitting device of claim 9, wherein the light emitting layer further comprises a compound represented by Chemical Formula H:
    [화학식 H][Formula H]
    Figure PCTKR2019006050-appb-I000133
    Figure PCTKR2019006050-appb-I000133
    상기 화학식 H에 있어서,In Chemical Formula H,
    L1 및 L2는 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이며,L1 and L2 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
    Ar5 및 Ar6는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,Ar5 and Ar6 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    R3는 수소; 중수소; 할로겐기; 니트릴기; 니트로기; 치환 또는 비치환된 사슬형 알킬기; 치환 또는 비치환된 사이클로알킬기; 알킬기 또는 아릴기로 치환 또는 비치환된 실릴기; 알킬기 또는 아릴기로 치환 또는 비치환된 포스핀옥사이드기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,R3 is hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; A substituted or unsubstituted chain alkyl group; A substituted or unsubstituted cycloalkyl group; A silyl group unsubstituted or substituted with an alkyl group or an aryl group; Phosphine oxide groups unsubstituted or substituted with alkyl or aryl groups; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    a는 0 내지 8의 정수이고, a가 2 이상인 경우 복수의 R3는 서로 동일하거나 상이하다.a is an integer of 0-8, and when a is 2 or more, some R <3> is the same or different from each other.
  12. 청구항 11에 있어서, 상기 화학식 H는 하기 화학식 H-1 또는 화학식 H-2로 표시되는 것인 유기 발광 소자:The organic light emitting diode of claim 11, wherein the chemical formula H is represented by the following chemical formula H-1 or H-2:
    [화학식 H-1][Formula H-1]
    Figure PCTKR2019006050-appb-I000134
    Figure PCTKR2019006050-appb-I000134
    [화학식 H-2][Formula H-2]
    Figure PCTKR2019006050-appb-I000135
    Figure PCTKR2019006050-appb-I000135
    상기 화학식 H-1 및 화학식 H-2에 있어서,In Chemical Formula H-1 and Chemical Formula H-2,
    L1, L2, R3 및 a의 정의는 화학식 H에서 정의한 바와 동일하고,The definitions of L1, L2, R3 and a are the same as defined in formula H,
    Ar7 내지 Ar9는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이며,Ar7 to Ar9 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group,
    HAr7는 치환 또는 비치환된 헤테로아릴기이다.HAr7 is a substituted or unsubstituted heteroaryl group.
  13. 청구항 11에 있어서, 상기 화학식 H로 표시되는 화합물은 하기 화합물들 중에서 선택된 어느 하나인 것인 화합물: The compound of claim 11, wherein the compound represented by Formula H is any one selected from the following compounds:
    Figure PCTKR2019006050-appb-I000136
    Figure PCTKR2019006050-appb-I000136
    Figure PCTKR2019006050-appb-I000137
    Figure PCTKR2019006050-appb-I000137
    Figure PCTKR2019006050-appb-I000138
    .
    Figure PCTKR2019006050-appb-I000138
    .
  14. 청구항 8에 있어서, 상기 유기물층은 정공 주입층, 정공 수송층, 정공 주입과 수송을 동시에 하는 층 또는 정공 조절층을 포함하고, 상기 정공 주입층, 정공 수송층, 정공 주입과 수송을 동시에 하는 층 또는 정공 조절층은 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 발광 소자.The method according to claim 8, wherein the organic layer comprises a hole injection layer, a hole transport layer, a hole injection layer and a hole control layer at the same time, the hole injection layer, a hole transport layer, a hole injection and transport at the same time or a hole control layer The layer is an organic light emitting device comprising the compound represented by Formula 1.
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