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WO2016024728A1 - Organic light-emitting element - Google Patents

Organic light-emitting element Download PDF

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Publication number
WO2016024728A1
WO2016024728A1 PCT/KR2015/007418 KR2015007418W WO2016024728A1 WO 2016024728 A1 WO2016024728 A1 WO 2016024728A1 KR 2015007418 W KR2015007418 W KR 2015007418W WO 2016024728 A1 WO2016024728 A1 WO 2016024728A1
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Prior art keywords
group
substituted
organic light
unsubstituted
light emitting
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PCT/KR2015/007418
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French (fr)
Korean (ko)
Inventor
허정오
이동훈
천민승
장분재
정원익
Original Assignee
주식회사 엘지화학
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Priority claimed from KR1020150028550A external-priority patent/KR101772746B1/en
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to EP15831494.8A priority Critical patent/EP3181657B1/en
Priority to JP2016569452A priority patent/JP6332885B2/en
Priority to CN201580029639.5A priority patent/CN106459745B/en
Priority to US14/912,537 priority patent/US9502669B2/en
Publication of WO2016024728A1 publication Critical patent/WO2016024728A1/en

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K99/00—Subject matter not provided for in other groups of this subclass
    • 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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers

Definitions

  • the present specification relates to an organic light emitting device.
  • the organic light emitting phenomenon is an example of converting an electric current into visible light by an internal process of a specific organic molecule.
  • the principle of the organic light emitting phenomenon is as follows.
  • An organic light emitting device using this principle may generally be composed of an organic material layer including a cathode and an anode, and an organic material layer disposed therebetween, such as a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.
  • the materials used in the organic light emitting device are pure organic materials or complex compounds in which organic materials and metals are complexed, and depending on the purpose, hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc. It can be divided into.
  • the hole injection material or the hole transport material an organic material having a p-type property, that is, an organic material which is easily oxidized and has an electrochemically stable state during oxidation, is mainly used.
  • organic materials having n-type properties that is, organic materials that are easily reduced and have an electrochemically stable state at the time of reduction are mainly used.
  • the light emitting layer material a material having a p-type property and an n-type property at the same time, that is, a material having a stable form in both oxidation and reduction states, and a material having high luminous efficiency that converts it to light when excitons are formed desirable.
  • An object of the present specification is to provide an organic light emitting device having a high luminous efficiency.
  • the present specification is a cathode; An anode provided opposite the cathode; A light emitting layer provided between the cathode and the anode; An electron transport layer provided between the cathode and the light emitting layer; And an electron adjusting layer provided between the light emitting layer and the electron transport layer.
  • the electron transport layer includes an organic compound containing an aromatic hetero ring,
  • the electron control layer comprises a heterocyclic compound represented by the formula (1),
  • the ionization potential Ip m of the electron transport layer is larger than the ionization potential Ip a of the electron control layer.
  • X1 is CR1 or N
  • X2 is CR2 or N
  • Y1 is CR5 or N
  • Y2 is CR6 or N
  • Y3 is CR7 or N
  • Y4 is CR8 or N
  • Z1 is CR9 or N
  • Z2 is CR10 or N
  • Z3 is CR11 or N
  • Z4 is CR12 or N
  • X1, X2, Y1 to Y4 and Z1 to Z4 are not N at the same time
  • R1, R2 and R5 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or a substituted or unsubstituted phosphine oxide group, or adjacent substituents of R1, R2, and R5 to R12 combine with each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heteroring.
  • the organic light emitting diode according to the exemplary embodiment of the present specification provides a low driving voltage and / or high efficiency.
  • FIG. 1 illustrates an example of an organic light emitting diode according to an exemplary embodiment of the present specification.
  • the present specification is a cathode; An anode provided opposite the cathode; A light emitting layer provided between the cathode and the anode; An electron transport layer provided between the cathode and the light emitting layer; And an electron control layer provided between the emission layer and the electron transport layer, wherein the transport layer includes an organic compound containing an aromatic hetero ring, and the electron control layer comprises a heterocyclic compound represented by Formula 1 above. It provides an organic light emitting device.
  • the electron control layer refers to a layer that controls the mobility of electrons according to the energy level of the light emitting layer in the organic light emitting device.
  • the ionization potential Ip m of the electron transport layer is larger than the ionization potential Ip a of the electron control layer.
  • the hole supplied from the anode may serve as a hole barrier so as not to fall toward the cathode, and the ability to adjust the electron mobility of the electron adjusting layer may be maximized.
  • the electron control layer is provided in contact with the light emitting layer.
  • the electron adjusting layer may simultaneously play a role of controlling electron mobility and a factory wall to prevent holes from being supplied from the anode to the cathode, in particular, the electron transport layer.
  • the thickness of the electron transport layer is thicker than the thickness of the electron control layer.
  • the thickness of the electron control layer that controls the movement of electrons is thicker than the thickness of the electron transport layer, the amount of electrons that can move to the light emitting layer per unit time is reduced, so that holes from the anode are supplied excessively to the cathode, thereby decreasing the efficiency of the device. have. Therefore, when the thickness of the electron transport layer is greater than the thickness of the electron control layer, the amount of electrons that can move to the light emitting layer per unit time can be properly adjusted to balance the amount of holes supplied from the anode to maximize the exciton formation of the light emitting layer and High device efficiency can be expected.
  • the light emitting layer includes a host and a dopant.
  • the dopant is a fluorescent dopant.
  • the dopant is a blue fluorescent dopant.
  • the organic light emitting device emits blue fluorescent light.
  • Organic light emitting devices currently used in the art are used in a combination of blue fluorescence, green and red phosphorescence or blue fluorescence and green fluorescence and red phosphorescence.
  • an organic light emitting device that emits blue fluorescent light having a high exciton energy
  • there is a problem in that the life of the device is considerably shorter than that of green or red. That is, since the high exciton energy of the blue fluorescence is concentrated in a local region called a narrow light emitting region, the energy stress applied to the material increases, resulting in a low lifetime. Therefore, in order to overcome the above problems, a separate electron control layer may be provided in the light emitting layer and the electron transport layer in addition to the electron transport layer to artificially adjust the amount of electrons to improve the efficiency and lifespan of the organic light emitting device.
  • the electron transport layer includes an organic compound containing an aromatic heterocycle.
  • containing an aromatic heterocycle herein may mean that the compound included in the electron transport layer includes an aromatic heterocycle as a core, or at least one of the substituents of the compound included in the electron transport layer is an aromatic heterocycle.
  • the electron transport layer includes an organic compound containing a nitrogen-containing monocyclic ring or a nitrogen-containing polycyclic ring.
  • the nitrogen-containing monocyclic ring means a ring in which at least one nitrogen atom is substituted in the ring member of a monocyclic hydrocarbon, for example, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a tetrazine group, Pentazine groups, pyrrole groups, thiazole groups, imidazole groups, and oxazole groups, but are not limited thereto.
  • a monocyclic hydrocarbon for example, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a tetrazine group, Pentazine groups, pyrrole groups, thiazole groups, imidazole groups, and oxazole groups, but are not limited thereto.
  • the nitrogen-containing polycyclic ring means a ring in which at least one nitrogen atom is substituted in the ring member of the polycyclic hydrocarbon, and a quinoline group, a cynoline group, a quinazoline group, a quinoxaline group, a pyridopyrazine group, and a pyrazinopyrazine Groups, pyrazinoquinoxaline groups, acridine groups, phenanthroline groups, benzimidazole groups, benzimidazophenanthridine groups, benzobenzimidazopefentridine groups and the like, but are not limited thereto.
  • the electron transport layer includes an organic compound containing a nitrogen-containing monocyclic ring.
  • the organic compound containing the aromatic hetero ring includes an aromatic hetero ring as a core.
  • X1 and X2 are CR1 and CR2, respectively, and R1 and R2 combine with each other to form a substituted or unsubstituted hydrocarbon ring.
  • R1 and R2 combine with each other to form a substituted or unsubstituted benzene ring.
  • R1 and R2 combine with each other to form a benzene ring.
  • X1 is N.
  • X2 is CR2.
  • R7 and R8 combine with each other to form a hydrocarbon ring.
  • R7 and R8 combine with each other to form a benzene ring.
  • R5 and R6 combine with each other to form a hydrocarbon ring.
  • R5 and R6 combine with each other to form a benzene ring.
  • the benzene ring or hydrocarbon ring may be substituted or unsubstituted.
  • the heterocyclic compound represented by Formula 1 is represented by the following Formula 1A or Formula 1B.
  • Y1 to Y4, Z1 to Z4 and R2 are the same as defined in Formula 1,
  • X3 to X6 are the same as or different from each other, and each independently CR3 or N,
  • Each R 3 is independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or a substituted or unsubstituted phosphine oxide group, or adjacent substituents are bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heteroring.
  • Y1 is CR5.
  • Y2 is CR6
  • Y3 is CR7.
  • Y4 is CR8.
  • Z1 is CR9.
  • Z2 is CR10.
  • Z3 is CR11.
  • Z4 is CR12.
  • X3 to X6 are each CR3.
  • each CR3 of the X3 to X6 may be the same or different from each other.
  • the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.
  • a, b and c are each an integer of 1 to 4,
  • d and e are each an integer of 1 to 6,
  • A1 to A5 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or a substituted or unsubstituted phosphine oxide group.
  • At least one of R1, R2, and R5 to R12 is substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group or Unsubstituted aryl group; Or a phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group, or adjacent substituents are bonded to each other to form a cyano group, an aryl A hydrocarbon ring substituted or unsubstituted with one or two or more substituents selected from the group consisting of a group, a heterocyclic group and a phosphine oxide group is formed.
  • At least one of R1 to R3 and R5 to R12 is substituted or unsubstituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group Ring aryl group; Or a phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group, or adjacent substituents are bonded to each other to form a cyano group, an aryl A benzene ring unsubstituted or substituted with one or two or more substituents selected from the group consisting of a group, a heterocyclic group and a phosphine oxide group is formed.
  • R1 to R3 and R5 to R12 are the same as or different from each other, and each independently hydrogen; An aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group; Or a phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group, or adjacent substituents are bonded to each other to form a cyano group, an aryl A benzene ring unsubstituted or substituted with one or two or more substituents selected from the group consisting of a group, a heterocyclic group and a phosphine oxide group is formed.
  • R1 to R3 and R5 to R12 are the same as or different from each other, and each independently hydrogen; A phenyl group substituted with a pyridine group; A phenyl group substituted with a quinoline group; Phenyl group substituted with pyrene group; A naphthyl group substituted with a phenyl group substituted with a naphthyl group; Naphthyl group substituted with phenanthrenyl group; A fluorenyl group substituted with one or two or more substituents selected from the group consisting of Formula 1B and a phenyl group; A naphthyl group substituted with a phenyl group substituted with a cyano group; A phenyl group substituted with an anthracene group substituted with a naphthyl group; A naphthyl group substituted with a phosphine oxide group substituted with an aryl group; Phosphine oxide groups substituted
  • R1 is hydrogen
  • R2 is hydrogen
  • R2 is a substituted or unsubstituted aryl group.
  • R2 is an aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
  • R2 is an aryl group which is substituted with a substituted or unsubstituted aryl group.
  • R2 is an aryl group which is substituted with a pyrene group.
  • R2 is a phenyl group substituted with a substituted or unsubstituted aryl group.
  • R2 is a phenyl group substituted with a pyrene group.
  • R2 is a phenyl group substituted with a substituted or unsubstituted anthracene group.
  • R2 is a phenyl group substituted with an anthracene group substituted with a naphthyl group.
  • R2 is a naphthyl group which is substituted with a substituted or unsubstituted aryl group.
  • R2 is a naphthyl group substituted with a phenanthrenyl group.
  • R2 is a naphthyl group which is substituted with a substituted or unsubstituted phenyl group.
  • R2 is a naphthyl group substituted with a phenyl group substituted with a cyano group.
  • R2 is a naphthyl group substituted with a phenyl group substituted with a naphthyl group.
  • R2 is a fluorenyl group which is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted Formula 1B and a phenyl group.
  • R2 is a fluorenyl group substituted with Formula 1B and a naphthyl group.
  • R3 is hydrogen
  • R3 is a substituted or unsubstituted aryl group.
  • R3 is a phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
  • R3 is an aryl group which is substituted with an aryl group.
  • R3 is an aryl group which is substituted with a naphthyl group.
  • R3 is a phenyl group substituted with a naphthyl group.
  • R3 is an aryl group which is substituted with a phenyl group.
  • R3 is a phenyl group substituted with an aryl group.
  • R3 is a naphthyl group which is substituted with an aryl group.
  • R3 is a phenyl group substituted with a phenyl group.
  • R3 is a naphthyl group which is substituted with a phenyl group.
  • R3 is an unsubstituted aryl group.
  • R3 is a naphthyl group.
  • R3 is a phenanthrenyl group.
  • R3 is a terphenyl group.
  • R3 is a triphenylene group.
  • R3 is a biphenyl group.
  • R3 is an aryl group substituted with a heterocyclic group.
  • R3 is an aryl group which is substituted with a pyridine group.
  • R3 is a phenyl group substituted with a pyridine group.
  • R3 is an aryl group substituted with a phosphine oxide group.
  • R3 is a naphthyl group substituted with a phosphine oxide group.
  • R3 is a naphthyl group substituted with a phosphine oxide group substituted with an aryl group.
  • R3 is a naphthyl group substituted with a phosphine oxide group substituted with a phenyl group.
  • R3 is a phosphine oxide group substituted with an aryl group.
  • R3 is a phosphine oxide group substituted with a naphthyl group.
  • R5 is hydrogen
  • R6 is hydrogen
  • R6 is a substituted or unsubstituted aryl group.
  • R6 is an aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
  • R6 is an aryl group substituted with a heterocyclic group.
  • R6 is an aryl group which is substituted with a pyridine group.
  • R6 is a phenyl group substituted with a pyridine group.
  • R7 is hydrogen
  • R7 is an aryl group substituted with a phosphine oxide group.
  • R7 is a naphthyl group substituted with a phosphine oxide group.
  • R7 is a naphthyl group substituted with a phosphine oxide group substituted with an aryl group.
  • R7 is a naphthyl group substituted with a phosphine oxide group substituted with a phenyl group.
  • R7 is a substituted or unsubstituted aryl group.
  • R7 is an aryl group which is unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
  • R7 is an aryl group substituted with a heterocyclic group.
  • R7 is an aryl group which is substituted with a quinoline group.
  • R7 is a phenyl group substituted with a quinoline group.
  • R8 is hydrogen
  • R9 is hydrogen
  • R10 is hydrogen
  • R10 is a substituted or unsubstituted aryl group.
  • R10 is an aryl group which is unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
  • R10 is an aryl group substituted with a heterocyclic group.
  • R10 is an aryl group which is substituted with a quinoline group.
  • R10 is a phenyl group substituted with a quinoline group.
  • R11 is hydrogen
  • R12 is hydrogen
  • At least one of A1 to A3 is an aryl group which is unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group ; Or a phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
  • A1 to A5 are the same as or different from each other, and each independently hydrogen; An aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group; Or a phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
  • A1 to A5 are the same as or different from each other, and each independently hydrogen; A phenyl group substituted with a pyridine group; A phenyl group substituted with a quinoline group; Phenyl group substituted with pyrene group; A naphthyl group substituted with a phenyl group substituted with a naphthyl group; Naphthyl group substituted with phenanthrenyl group; A fluorenyl group substituted with one or two or more substituents selected from the group consisting of Formula 1B and a phenyl group; A naphthyl group substituted with a phenyl group substituted with a cyano group; A phenyl group substituted with an anthracene group substituted with a naphthyl group; A naphthyl group substituted with a phosphine oxide group substituted with an aryl group; Phosphine oxide groups substituted with naphthyl
  • At least one of the R1 to R3 and R5 to R12 is selected from the following structure.
  • At least one of A1 to A5 may be selected from the structures.
  • the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1-1 to 1-1-7.
  • the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-2-1 to 1-2-10.
  • the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-3-1 to 1-3-5.
  • the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-4-1 to 1-4-7.
  • the electron transport layer includes an organic compound containing an aromatic hetero ring represented by the following formula (2).
  • X5 and X6 are the same as or different from each other, and each independently N or CH,
  • Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • At least one of Ar1 to Ar3 is represented by the following formula (3).
  • o, p and q are 0 or 1
  • r 1 or 2
  • L1 to L3 are the same as or different from each other, and each independently a phenylene group; Or naphthalene group; Or a fluorenylene group,
  • Ar is an aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group; Or a heterocyclic group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group.
  • o is 1.
  • o is zero.
  • p 0.
  • p is 1.
  • q is 0.
  • q is one.
  • r is 1.
  • r is two.
  • L1 is a phenylene group.
  • L1 is a naphthalene group.
  • L1 is a fluorenylene group.
  • L2 is a phenylene group.
  • L2 is a naphthalene group.
  • L2 is a fluorenylene group.
  • L3 is a phenylene group.
  • L3 is a naphthalene group.
  • L3 is a fluorenylene group.
  • Ar is an aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group; Or a heterocyclic group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group.
  • Ar is a heterocyclic group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group.
  • Ar is a quinoline group.
  • Ar is a heterocyclic group unsubstituted or substituted with an aryl group.
  • Ar is a heterocyclic group which is unsubstituted or substituted with a phenyl group.
  • Ar is a pyrimidine group substituted with a phenyl group.
  • Ar is a pyridine group substituted with a phenyl group.
  • Ar is a triazine group substituted with a phenyl group.
  • Ar is a pyridine group.
  • Ar is a carbazole group.
  • Ar is an aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group.
  • Ar is a phenyl group.
  • Ar is an aryl group which is substituted with an aryl group.
  • Ar is an aryl group which is substituted with a phenyl group.
  • Ar is a fluorenyl group substituted with a phenyl group.
  • Ar1 to Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted fluorenyl group.
  • Ar1 to Ar3 are the same as or different from each other, and each independently phenyl; Biphenyl; naphthalene; Phenyl-naphthalene-phenyl-quinoline; Phenyl-naphthalene-phenyl-pyrimidine-phenyl; Phenyl-naphthalene-phenyl-pyridine-phenyl; Phenyl-naphthalene-phenyl-pyrimidine; Fluorene-phenyl; Phenyl-terphenyl; Biphenyl-phenyl; Naphthyl-fluorene-phenyl; Phenyl-fluorene-phenyl; Biphenyl-carbazole; Or phenyl-naphthalene-phenyl-triazine-phenyl.
  • the "-naphthalene-" is 2,7-naphthalene or 1,4-naphthalene.
  • the organic compound containing the aromatic hetero ring represented by Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-1 to 2-13.
  • substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted is deuterium; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents.
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
  • the aryl group is a monocyclic aryl group
  • carbon number is not particularly limited, but preferably 6 to 25 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-24.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
  • the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like.
  • carbon number is not specifically limited, It is preferable that it is C2-C60.
  • heterocyclic group examples include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridil group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthro
  • the heterocyclic group may be monocyclic or polycyclic, and may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic.
  • adjacent means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an atom to which the substituent is substituted.
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups.
  • the adjacent groups are bonded to each other to form a hydrocarbon ring or a hetero ring, in which the adjacent substituents form a bond, a 5- to 7-membered monocyclic or polycyclic hydrocarbon ring or a 5- to 7-membered monocyclic or multi It means forming the heterocyclic group of the ring.
  • the hydrocarbon ring is a cycloalkyl group; Cycloalkenyl group; Aromatic ring groups; Or include all aliphatic ring groups, which may be monocyclic or polycyclic, and include all rings condensed by combining one or two or more.
  • Heterocycle formed herein means that at least one carbon atom of the hydrocarbon ring is substituted with N, O, or S atoms, may be an aliphatic ring or an aromatic ring, it may be monocyclic or polycyclic.
  • the organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except for including an electron transport layer and an electron control layer.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate.
  • the anode is formed by depositing a metal or conductive metal oxide or an alloy thereof on the substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation.
  • PVD physical vapor deposition
  • an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, an electron adjusting layer, and an electron transporting layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer of the organic light emitting device of the present specification may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device further includes one or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer and a hole blocking layer. can do.
  • the structure of the organic light emitting device of the present specification may have a structure as shown in FIG. 1, but is not limited thereto.
  • 1 illustrates a structure of an organic light emitting device in which an anode 201, a light emitting layer 301, an electron control layer 401, an electron transport layer 501, and a cathode 601 are sequentially stacked on a substrate 101.
  • 1 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.
  • the organic material layers may be formed of the same material or different materials.
  • the anode material a material having a large work function is generally 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); ZnO: Al or SNO 2 : Combination of metals and oxides such as 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 generally 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 material is a layer for injecting holes from an electrode, and the hole injection material has a capability of transporting holes, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in a light emitting layer.
  • the compound which prevents the movement of the excited excitons to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is 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-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer.
  • the material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • 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 thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Dopant materials include organic compounds, metals or metal compounds.
  • Organic compounds as dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds and the like.
  • the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like but is not limited thereto.
  • a metal complex may be used as the metal or the metal compound.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • the electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer.
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and 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 hole blocking layer is a layer for blocking the arrival of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.
  • 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.
  • the organic light emitting diode according to the present disclosure may be a normal type in which the lower electrode is an anode and the upper electrode is a cathode, or may be an inverted type in which the lower electrode is a cathode and the upper electrode is an anode.
  • the structure according to the exemplary embodiment of the present specification may act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic solar cell, an organic photoconductor, an organic transistor, and the like.
  • a glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. was used as a detergent and Millipore Co. was used as distilled water. Secondly 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, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, and the like was dried and then transferred to a plasma cleaner. In addition, the substrate was dry-cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • ITO indium tin oxide
  • Hexanitrilehexaazatriphenylene (hereinafter referred to as HAT), a compound of the following formula, was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a thin film.
  • HAT Hexanitrilehexaazatriphenylene
  • a hole transport layer was formed by depositing a compound of Formula HT-1 at a thickness of 400 kPa on the thin film, and an electron blocking layer was formed by depositing a compound of EB-1 at a thickness of 250 kPa thereon.
  • the compound of the following H1 and the following D1 as a host of a light emitting layer was vacuum-deposited at 200 microsecond thickness on it.
  • Compound 1-1-1 was deposited to a thickness of 100 ⁇ on the emission layer to form an electron control layer, and the electron transport layer material of the compound 2-1 and lithium quinolate (LiQ, Lithium Quinolate) were added in a weight ratio of 1: 1. Vacuum deposition was carried out to form an electron injection and transport layer having a thickness of 300 kPa. A cathode was formed by sequentially depositing 12 ⁇ thick lithium fluoride (LiF) and 2,000 ⁇ thick aluminum on the electron transport layer.
  • LiQ lithium quinolate
  • the deposition rate of the organic material was maintained at 0.3 ⁇ 0.8 ⁇ / sec.
  • the lithium fluoride of the negative electrode maintained a deposition rate of 0.3 kPa / sec and aluminum of 1.5 to 2.5 kPa / sec.
  • the degree of vacuum was maintained at 1 to 3 ⁇ 10 ⁇ 7 .
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2-3 was used instead of Compound 2-1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2-4 was used instead of Compound 2-1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2-7 was used instead of Compound 2-1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2-8 was used instead of Compound 2-1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2-13 was used instead of Compound 2-1 in Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound 1-2-3 instead of the compound 1-1-1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Example 1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 2 except for using the compound 1-2-3 instead of the compound 1-1-1 in Example 2.
  • An organic light-emitting device was manufactured in the same manner as in Example 2, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Example 2.
  • An organic light-emitting device was manufactured in the same manner as in Example 2, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Example 2.
  • An organic light-emitting device was manufactured in the same manner as in Example 2, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Example 2.
  • An organic light-emitting device was manufactured in the same manner as in Example 2, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Example 2.
  • An organic light emitting diode was manufactured according to the same method as Example 3 except for using the compound 1-2-3 instead of the compound 1-1-1 in Example 3.
  • An organic light-emitting device was manufactured in the same manner as in Example 3, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Example 3.
  • An organic light-emitting device was manufactured in the same manner as in Example 3, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Example 3.
  • An organic light emitting diode was manufactured according to the same method as Example 3 except for using the compound 1-3-2 instead of the compound 1-1-1 in Example 3.
  • An organic light emitting diode was manufactured according to the same method as Example 3 except for using the compound 1-4-1 instead of the compound 1-1-1 in Example 3.
  • An organic light emitting diode was manufactured according to the same method as Example 4 except for using the compound 1-2-3 instead of the compound 1-1-1 in Example 4.
  • An organic light-emitting device was manufactured in the same manner as in Example 4, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Example 4.
  • An organic light-emitting device was manufactured in the same manner as in Example 4, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Example 4.
  • An organic light emitting diode was manufactured according to the same method as Example 4 except for using the compound 1-3-2 instead of the compound 1-1-1 in Example 4.
  • An organic light-emitting device was manufactured in the same manner as in Example 4, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Example 4.
  • An organic light emitting diode was manufactured according to the same method as Example 5 except for using the compound 1-2-3 instead of the compound 1-1-1 in Example 5.
  • An organic light emitting diode was manufactured according to the same method as Example 5 except for using the compound 1-2-10 instead of the compound 1-1-1 in Example 5.
  • An organic light-emitting device was manufactured in the same manner as in Example 5, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Example 5.
  • An organic light-emitting device was manufactured in the same manner as in Example 5, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Example 5.
  • An organic light-emitting device was manufactured in the same manner as in Example 5, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Example 5.
  • An organic light emitting diode was manufactured according to the same method as Example 6 except for using the compound 1-2-3 instead of the compound 1-1-1 in Example 6.
  • An organic light-emitting device was manufactured in the same manner as in Example 6, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Example 6.
  • An organic light emitting diode was manufactured according to the same method as Example 6 except for using the compound 1-3-1 instead of the compound 1-1-1 in Example 6.
  • An organic light-emitting device was manufactured in the same manner as in Example 6, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Example 6.
  • An organic light-emitting device was manufactured in the same manner as in Example 6, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Example 6.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the following Chemical Formula ET-1 instead of the compound 1-1-1 in Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 2 except for using the following Chemical Formula ET-1 instead of the compound 1-1-1 in Example 2.
  • An organic light emitting diode was manufactured according to the same method as Example 3 except for using the following Chemical Formula ET-1 instead of the compound 1-1-1 in Example 3.
  • An organic light emitting diode was manufactured according to the same method as Example 4 except for using the following Chemical Formula ET-1 instead of the compound 1-1-1 in Example 4.
  • An organic light emitting diode was manufactured according to the same method as Example 5 except for using the following Chemical Formula ET-1 instead of the compound 1-1-1 in Example 5.
  • An organic light emitting diode was manufactured according to the same method as Example 6 except for using the following Chemical Formula ET-1 instead of the compound 1-1-1 in Example 6.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the following Chemical Formula ET-2 instead of the compound 1-1-1 in Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 2 except for using the following Chemical Formula ET-2 instead of the compound 1-1-1 in Example 2.
  • An organic light emitting diode was manufactured according to the same method as Example 3 except for using the following Chemical Formula ET-2 instead of the compound 1-1-1 in Example 3.
  • An organic light emitting diode was manufactured according to the same method as Example 4 except for using the following Chemical Formula ET-2 instead of the compound 1-1-1 in Example 4.
  • An organic light emitting diode was manufactured according to the same method as Example 5 except for using the following Chemical Formula ET-2 instead of the compound 1-1-1 in Example 5.
  • An organic light emitting diode was manufactured according to the same method as Example 6 except for using the following Chemical Formula ET-2 instead of the compound 1-1-1 in Example 6.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the following Chemical Formula ET-3 instead of the compound 1-1-1 in Example 1.
  • An organic light emitting diode was manufactured according to the same method as Example 2 except for using the following Chemical Formula ET-3 instead of the compound 1-1-1 in Example 2.
  • An organic light emitting diode was manufactured according to the same method as Example 3 except for using the following Chemical Formula ET-3 instead of the compound 1-1-1 in Example 3.
  • An organic light emitting diode was manufactured according to the same method as Example 4 except for using the following Chemical Formula ET-3 instead of the compound 1-1-1 in Example 4.
  • An organic light emitting diode was manufactured according to the same method as Example 5 except for using the following Chemical Formula ET-3 instead of the compound 1-1-1 in Example 5.
  • An organic light emitting diode was manufactured according to the same method as Example 6 except for using the following Chemical Formula ET-3 instead of the compound 1-1-1 in Example 6.
  • Example 1 the electron transporting layer material of the compound 2-1 and lithium quinolate (LiQ, Lithium Quinolate) were vacuum-deposited at a weight ratio of 1 to 1 to form an electron injection and transport layer at a thickness of 400 Pa.
  • LiQ lithium quinolate
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 19, except that Compound 2-3 was used instead of Compound 2-1 in Comparative Example 19.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 19, except that Compound 2-4 was used instead of Compound 2-1 in Comparative Example 19.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 19, except that Compound 2-7 was used instead of Compound 2-1 in Comparative Example 19.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 19, except that Compound 2-8 was used instead of Compound 2-1 in Comparative Example 19.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 19, except that Compound 2-13 was used instead of Compound 2-1 in Comparative Example 19.
  • Example 1 the electron control layer was formed by depositing the compound 1-1-1 to a thickness of 300 ⁇ on the light emitting layer, and the electron transport layer material of the compound 2-1 and lithium quinolate (LiQ, Lithium Quinolate) 1 Vacuum deposition was carried out at a weight ratio of 1 to form an electron injection and transport layer at a thickness of 100 kPa.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 2-3 was used instead of Compound 2-1 in Comparative Example 25.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 2-4 was used instead of Compound 2-1 in Comparative Example 25.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 2-7 was used instead of Compound 2-1 in Comparative Example 25.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 2-8 was used instead of Compound 2-1 in Comparative Example 25.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 2-13 was used instead of Compound 2-1 in Comparative Example 25.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 1-2-3 was used instead of Compound 1-1-1 in Comparative Example 25.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Comparative Example 25.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Comparative Example 25.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Comparative Example 25.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Comparative Example 25.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 26, except that Compound 1-2-3 was used instead of Compound 1-1-1 in Comparative Example 26.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 26, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Comparative Example 26.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 26, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Comparative Example 26.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 26, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Comparative Example 26.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 26, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Comparative Example 26.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 27, except that Compound 1-2-3 was used instead of Compound 1-1-1 in Comparative Example 27.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 27, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Comparative Example 27.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 27, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Comparative Example 27.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 27, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Comparative Example 27.
  • An organic light emitting diode was manufactured according to the same method as Comparative Example except for using Compound 1-4-1 instead of Compound 1-1-1 in Comparative Example 27.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 28, except that Compound 1-2-3 was used instead of Compound 1-1-1 in Comparative Example 28.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 28, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Comparative Example 28.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 28, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Comparative Example 28.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 28, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Comparative Example 28.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 28, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Comparative Example 28.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 29, except that Compound 1-2-3 was used instead of Compound 1-1-1 in Comparative Example 29.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 29, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Comparative Example 29.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 29, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Comparative Example 29.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 29, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Comparative Example 29.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 29, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Comparative Example 29.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 30, except that Compound 1-2-3 was used instead of Compound 1-1-1 in Comparative Example 30.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 30, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Comparative Example 30.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 30, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Comparative Example 30.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 30, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Comparative Example 30.
  • An organic light-emitting device was manufactured in the same manner as in Comparative Example 30, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Comparative Example 30.
  • the driving voltage and the luminous efficiency of the organic light emitting device manufactured by the above-described method were measured at a current density of 10 mA / cm 2 , and the time (LT98) of 98% of the initial luminance at a current density of 20 mA / cm 2 was measured. .
  • the results are shown in Table 1 below.
  • an organic light emitting device having high efficiency and / or long life may be provided.

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Abstract

The present specification relates to an organic light-emitting element, which comprises: a cathode; an anode formed opposite to the cathode; a light-emitting layer formed between the cathode and the anode; and an electron transport layer formed between the cathode and the light-emitting layer; and an electron adjustment layer formed between the light-emitting layer and the electron transport layer, wherein the electron transport layer includes an organic compound containing an aromatic hetero ring, the electron adjustment layer includes a hetero ring compound represented by chemical formula 1, and the ionization potential (Ipm) of the electron transport layer is larger than the ionization potential (Ipa) of the electron adjustment layer.

Description

유기 발광 소자Organic light emitting device
본 명세서는 2014년 8월 12일에 한국특허청에 제출된 한국 특허 출원 제 10-2014-0104507호 및 2015년 2월 27일에 한국특허청에 제출된 한국 특허 출원 제 10-2015-0028550호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This specification describes the Korean Patent Application No. 10-2014-0104507 filed with the Korean Patent Office on August 12, 2014 and the Korean Patent Application No. 10-2015-0028550 filed with the Korean Patent Office on February 27, 2015. Claiming benefit, the entire contents of which are incorporated herein by reference.
본 명세서는 유기 발광 소자에 관한 것이다.The present specification relates to an organic light emitting device.
유기 발광 현상은 특정 유기 분자의 내부 프로세스에 의하여 전류가 가시광으로 전환되는 예의 하나이다. 유기 발광 현상의 원리는 다음과 같다.The organic light emitting phenomenon is an example of converting an electric current into visible light by an internal process of a specific organic molecule. The principle of the organic light emitting phenomenon is as follows.
양극과 음극 사이에 유기물층을 위치시켰을 때 두 전극 사이에 전압을 걸어주게 되면 음극과 양극으로부터 각각 전자와 정공이 유기물층으로 주입된다. 유기물층으로 주입된 전자와 정공은 재결합하여 엑시톤(exciton)을 형성하고, 이 엑시톤이 다시 바닥 상태로 떨어지면서 빛이 나게 된다. 이러한 원리를 이용하는 유기 발광 소자는 일반적으로 음극과 양극 및 그 사이에 위치한 유기물층, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층을 포함하는 유기물층으로 구성될 수 있다.When the organic material layer is placed between the anode and the cathode, when a voltage is applied between the two electrodes, electrons and holes are injected into the organic material layer from the cathode and the anode, respectively. Electrons and holes injected into the organic material layer recombine to form excitons, and the excitons fall back to the ground to shine. An organic light emitting device using this principle may generally be composed of an organic material layer including a cathode and an anode, and an organic material layer disposed therebetween, such as a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer.
유기 발광 소자에서 사용되는 물질로는 순수 유기 물질 또는 유기 물질과 금속이 착물을 이루는 착화합물이 대부분을 차지하고 있으며, 용도에 따라 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질 등으로 구분될 수 있다. 여기서, 정공주입 물질이나 정공수송 물질로는 p-타입의 성질을 가지는 유기물질, 즉 쉽게 산화가 되고 산화시에 전기화학적으로 안정한 상태를 가지는 유기물이 주로 사용되고 있다. 한편, 전자주입 물질이나 전자수송 물질로는 n-타입 성질을 가지는 유기 물질, 즉 쉽게 환원이 되고 환원시에 전기화학적으로 안정한 상태를 가지는 유기물이 주로 사용되고 있다. 발광층 물질로는 p-타입 성질과 n-타입 성질을 동시에 가진 물질, 즉 산화와 환원 상태에서 모두 안정한 형태를 갖는 물질이 바람직하며, 엑시톤이 형성되었을 때 이를 빛으로 전환하는 발광 효율이 높은 물질이 바람직하다.Most of the materials used in the organic light emitting device are pure organic materials or complex compounds in which organic materials and metals are complexed, and depending on the purpose, hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, etc. It can be divided into. Here, as the hole injection material or the hole transport material, an organic material having a p-type property, that is, an organic material which is easily oxidized and has an electrochemically stable state during oxidation, is mainly used. On the other hand, as an electron injection material or an electron transport material, organic materials having n-type properties, that is, organic materials that are easily reduced and have an electrochemically stable state at the time of reduction are mainly used. As the light emitting layer material, a material having a p-type property and an n-type property at the same time, that is, a material having a stable form in both oxidation and reduction states, and a material having high luminous efficiency that converts it to light when excitons are formed desirable.
당 기술분야에서는 높은 효율의 유기 발광 소자의 개발이 요구되고 있다.There is a need in the art for the development of high efficiency organic light emitting devices.
[선행기술문헌][Preceding technical literature]
[비특허문헌][Non-Patent Documents]
Applied Physics Letters 51, p. 913, 1987Applied Physics Letters 51, p. 913, 1987
본 명세서의 목적은 높은 발광 효율의 유기 발광 소자를 제공하는 데 있다.An object of the present specification is to provide an organic light emitting device having a high luminous efficiency.
본 명세서는 캐소드; 상기 캐소드와 대향하여 구비된 애노드; 상기 캐소드와 상기 애노드 사이에 구비된 발광층; 상기 캐소드와 상기 발광층 사이에 구비된 전자수송층; 및 상기 발광층과 상기 전자수송층 사이에 구비된 전자조절층을 포함하고, The present specification is a cathode; An anode provided opposite the cathode; A light emitting layer provided between the cathode and the anode; An electron transport layer provided between the cathode and the light emitting layer; And an electron adjusting layer provided between the light emitting layer and the electron transport layer.
상기 전자수송층은 방향족 헤테로고리를 함유하는 유기화합물을 포함하며, The electron transport layer includes an organic compound containing an aromatic hetero ring,
상기 전자조절층은 하기 화학식 1로 표시되는 헤테로환 화합물을 포함하고, The electron control layer comprises a heterocyclic compound represented by the formula (1),
상기 전자수송층의 이온화퍼텐셜(Ipm)은 상기 전자조절층의 이온화퍼텐셜(Ipa)보다 큰 것인 유기 발광 소자를 제공한다. The ionization potential Ip m of the electron transport layer is larger than the ionization potential Ip a of the electron control layer.
[화학식 1][Formula 1]
Figure PCTKR2015007418-appb-I000001
Figure PCTKR2015007418-appb-I000001
화학식 1에 있어서, In Chemical Formula 1,
X1은 CR1 또는 N이고, X2는 CR2 또는 N이며,X1 is CR1 or N, X2 is CR2 or N,
Y1은 CR5 또는 N이고, Y2는 CR6 또는 N이며, Y3는 CR7 또는 N이고, Y4는 CR8 또는 N이며, Y1 is CR5 or N, Y2 is CR6 or N, Y3 is CR7 or N, Y4 is CR8 or N,
Z1은 CR9 또는 N이고, Z2는 CR10 또는 N이며, Z3는 CR11 또는 N이고, Z4는 CR12 또는 N이며, Z1 is CR9 or N, Z2 is CR10 or N, Z3 is CR11 or N, Z4 is CR12 or N,
X1, X2, Y1 내지 Y4 및 Z1 내지 Z4는 동시에 N은 아니고, X1, X2, Y1 to Y4 and Z1 to Z4 are not N at the same time,
R1, R2 및 R5 내지 R12는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기; 또는 치환 또는 비치환된 포스핀옥사이드기이거나, R1, R2 및 R5 내지 R12 중 인접하는 치환기는 서로 결합하여 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리를 형성한다.R1, R2 and R5 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or a substituted or unsubstituted phosphine oxide group, or adjacent substituents of R1, R2, and R5 to R12 combine with each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heteroring.
본 명세서의 일 실시상태에 따른 유기 발광 소자는 낮은 구동 전압 및/또는 높은 효율을 제공한다.The organic light emitting diode according to the exemplary embodiment of the present specification provides a low driving voltage and / or high efficiency.
도 1 은 본 명세서의 일 실시상태에 따른 유기 발광 소자의 예를 도시한 것이다. 1 illustrates an example of an organic light emitting diode according to an exemplary embodiment of the present specification.
[부호의 설명][Description of the code]
101: 기판101: substrate
201: 애노드201: anode
301: 발광층 301: light emitting layer
401: 전자조절층401: electronic control layer
501: 전자수송층501: electron transport layer
601: 캐소드601 cathode
이하, 본 명세서에 대하여 더욱 상세하게 설명한다.Hereinafter, this specification is demonstrated in detail.
본 명세서에서 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다. In the present specification, when a part "contains" a certain component, this means that the component may further include other components, except for the case where there is no contrary description.
본 명세서는 캐소드; 상기 캐소드와 대향하여 구비된 애노드; 상기 캐소드와 상기 애노드 사이에 구비된 발광층; 상기 캐소드와 상기 발광층 사이에 구비된 전자수송층; 및 상기 발광층과 상기 전자수송층 사이에 구비된 전자조절층을 포함하고, 상기 수송층은 방향족 헤테로고리를 함유하는 유기화합물을 포함하며, 상기 전자조절층은 상기 화학식 1로 표시되는 헤테로환 화합물을 포함하는 것인 유기 발광 소자를 제공한다. The present specification is a cathode; An anode provided opposite the cathode; A light emitting layer provided between the cathode and the anode; An electron transport layer provided between the cathode and the light emitting layer; And an electron control layer provided between the emission layer and the electron transport layer, wherein the transport layer includes an organic compound containing an aromatic hetero ring, and the electron control layer comprises a heterocyclic compound represented by Formula 1 above. It provides an organic light emitting device.
상기 전자조절층은 유기 발광 소자에서 발광층의 에너지 준위에 따라서, 전자의 이동도를 조절하는 역할을 하는 층을 의미한다. The electron control layer refers to a layer that controls the mobility of electrons according to the energy level of the light emitting layer in the organic light emitting device.
본 명세서의 일 실시상태에 있어서, 상기 전자수송층의 이온화퍼텐셜(Ipm)은 상기 전자조절층의 이온화퍼텐셜(Ipa)보다 크다. 이 경우, 애노드에서 공급되는 정공이 캐소드 쪽으로 넘어가지 않도록 정공 장벽의 역할을 할 수 있고, 전자조절층의 전자 이동도의 조절 능력이 극대화될 수 있다.In one embodiment of the present specification, the ionization potential Ip m of the electron transport layer is larger than the ionization potential Ip a of the electron control layer. In this case, the hole supplied from the anode may serve as a hole barrier so as not to fall toward the cathode, and the ability to adjust the electron mobility of the electron adjusting layer may be maximized.
본 명세서의 일 실시상태에 있어서, 상기 전자조절층은 상기 발광층과 접하여 구비된다. 이 경우, 전자조절층은 전자 이동도를 조절하는 역할 및 애노드로부터 공급되는 정공이 캐소드 특히, 전자수송층으로 넘어가지 않도록 하는 정공장벽 역할을 동시에 수행할 수 있다. In one embodiment of the present specification, the electron control layer is provided in contact with the light emitting layer. In this case, the electron adjusting layer may simultaneously play a role of controlling electron mobility and a factory wall to prevent holes from being supplied from the anode to the cathode, in particular, the electron transport layer.
본 명세서의 일 실시상태에 있어서, 상기 전자수송층의 두께는 상기 전자조절층의 두께보다 두껍다. 전자의 이동을 조절하는 전자조절층의 두께가 전자수송층의 두께보다 두꺼울 경우에는 단위 시간 당 발광층으로 이동할 수 있는 전자의 양이 줄어 상대적으로 애노드로부터 정공이 캐소드로 지나치게 공급되어 소자의 효율이 낮아질 수 있다. 따라서, 전자 수송층의 두께가 전자조절층의 두께보다 두껴운 경우에는 단위 시간당 발광층으로 이동할 수 있는 전자의 양을 적절히 조절하여 애노드로부터 공급되는 정공의 양과 균형을 맞출 수 있어 발광층의 엑시톤 형성의 극대화 및 높은 소자의 효율을 기대할 수 있다. In one embodiment of the present specification, the thickness of the electron transport layer is thicker than the thickness of the electron control layer. When the thickness of the electron control layer that controls the movement of electrons is thicker than the thickness of the electron transport layer, the amount of electrons that can move to the light emitting layer per unit time is reduced, so that holes from the anode are supplied excessively to the cathode, thereby decreasing the efficiency of the device. have. Therefore, when the thickness of the electron transport layer is greater than the thickness of the electron control layer, the amount of electrons that can move to the light emitting layer per unit time can be properly adjusted to balance the amount of holes supplied from the anode to maximize the exciton formation of the light emitting layer and High device efficiency can be expected.
본 명세서의 하나의 실시상태에 있어서, 상기 발광층은 호스트 및 도펀트를 포함한다. In one embodiment of the present specification, the light emitting layer includes a host and a dopant.
또 하나의 실시상태에 있어서, 상기 도펀트는 형광 도펀트이다.In another embodiment, the dopant is a fluorescent dopant.
또 하나의 실시상태에 있어서, 상기 도펀트는 청색 형광 도펀트이다. In another embodiment, the dopant is a blue fluorescent dopant.
본 명세서의 일 실시상태에 따른 유기 발광 소자는 청색 형광 발광을 한다. The organic light emitting device according to the exemplary embodiment of the present specification emits blue fluorescent light.
현재 당업계에서 사용하고 있는 유기 발광 소자는 청색 형광, 녹색 및 적색 인광 또는 청색 형광과 녹색 형광 및 적색 인광 등의 조합으로 사용되고 있다. 다만, 높은 엑시톤 에너지를 가지는 청색 형광 발광을 하는 유기 발광 소자의 경우에는 녹색 또는 적색에 비하여 상대적으로 소자의 수명이 현저히 떨어지는 문제가 있다. 즉, 청색 형광의 높은 엑시톤 에너지가 좁은 발광영역이라는 국부적인 영역에 집중되어 있기 때문에 재료가 받는 에너지 스트레스가 증가하게 되고 결국 낮은 수명을 나타내게 된다. 따라서 상기와 같은 문제를 극복하기 위하여 전자수송층 외에 별도의 전자조절층을 발광층과 전자수송층에 구비하여 인위적으로 전자의 양을 조절하여 유기 발광 소자의 효율 및 수명을 향상시킬 수 있다.Organic light emitting devices currently used in the art are used in a combination of blue fluorescence, green and red phosphorescence or blue fluorescence and green fluorescence and red phosphorescence. However, in the case of an organic light emitting device that emits blue fluorescent light having a high exciton energy, there is a problem in that the life of the device is considerably shorter than that of green or red. That is, since the high exciton energy of the blue fluorescence is concentrated in a local region called a narrow light emitting region, the energy stress applied to the material increases, resulting in a low lifetime. Therefore, in order to overcome the above problems, a separate electron control layer may be provided in the light emitting layer and the electron transport layer in addition to the electron transport layer to artificially adjust the amount of electrons to improve the efficiency and lifespan of the organic light emitting device.
본 명세서의 일 실시상태에 있어서, 전자수송층은 방향족 헤테로고리를 함유하는 유기 화합물을 포함한다. In one embodiment of the present specification, the electron transport layer includes an organic compound containing an aromatic heterocycle.
본 명세서에서 방향족 헤테로고리를 함유한다는 의미는 전자수송층에 포함되는 화합물이 방향족 헤테로고리가 코어로 포함되거나, 전자수송층에 포함되는 화합물의 치환기 중 적어도 하나가 방향족 헤테로고리인 것을 의미할 수 있다.The term “containing an aromatic heterocycle” herein may mean that the compound included in the electron transport layer includes an aromatic heterocycle as a core, or at least one of the substituents of the compound included in the electron transport layer is an aromatic heterocycle.
또 하나의 실시상태에 있어서, 전자수송층은 함질소 단환 고리 또는 함질소 다환 고리를 함유하는 유기 화합물을 포함한다. In another exemplary embodiment, the electron transport layer includes an organic compound containing a nitrogen-containing monocyclic ring or a nitrogen-containing polycyclic ring.
상기 함질소 단환 고리란, 단환의 탄화 수소의 고리원 내에 탄소 대신 질소 원자가 적어도 하나 치환된 고리를 의미하며, 예컨대, 피리딘기, 피리미딘기, 피리다진기, 피라진기, 트리아진기, 테트라진기, 펜타진기, 피롤기, 티아졸기, 이미다졸기 및 옥사졸기 등이 있으나, 이에 한정하지 않는다. The nitrogen-containing monocyclic ring means a ring in which at least one nitrogen atom is substituted in the ring member of a monocyclic hydrocarbon, for example, a pyridine group, a pyrimidine group, a pyridazine group, a pyrazine group, a triazine group, a tetrazine group, Pentazine groups, pyrrole groups, thiazole groups, imidazole groups, and oxazole groups, but are not limited thereto.
상기 함질소 다환 고리란 다환의 탄화 수소의 고리원 내에 탄소 대신 질소 원자가 적어도 하나 치환된 고리를 의미하며, 퀴놀린기, 시놀린기, 퀴나졸린기, 퀴녹살린기, 피리도피라진기, 피라지노피라진기, 피라지노퀴녹살린기, 아크리딘기, 페난트롤린기, 벤즈이미다졸기, 벤즈이미다조페난트리딘기, 벤조벤즈이미다조페난트리딘기 등이 있으나, 이에 한정하지 않는다. The nitrogen-containing polycyclic ring means a ring in which at least one nitrogen atom is substituted in the ring member of the polycyclic hydrocarbon, and a quinoline group, a cynoline group, a quinazoline group, a quinoxaline group, a pyridopyrazine group, and a pyrazinopyrazine Groups, pyrazinoquinoxaline groups, acridine groups, phenanthroline groups, benzimidazole groups, benzimidazophenanthridine groups, benzobenzimidazopefentridine groups and the like, but are not limited thereto.
본 명세서의 일 실시상태에 있어서, 상기 전자수송층은 함질소 단환고리를 함유하는 유기 화합물을 포함한다. In one embodiment of the present specification, the electron transport layer includes an organic compound containing a nitrogen-containing monocyclic ring.
본 명세서의 일 실시상태에 있어서, 상기 방향족 헤테로고리를 함유하는 유기화합물은 방향족 헤테로고리가 코어로 포함된다. In an exemplary embodiment of the present specification, the organic compound containing the aromatic hetero ring includes an aromatic hetero ring as a core.
본 명세서의 일 실시상태에 있어서, 상기 X1 및 X2는 각각 CR1 및 CR2이고, 상기 R1 및 R2는 서로 결합하여 치환 또는 비치환된 탄화수소고리를 형성한다. In one embodiment of the present specification, X1 and X2 are CR1 and CR2, respectively, and R1 and R2 combine with each other to form a substituted or unsubstituted hydrocarbon ring.
본 명세서의 일 실시상태에 있어서, R1 및 R2는 서로 결합하여, 치환 또는 비치환된 벤젠고리를 형성한다. In one embodiment of the present specification, R1 and R2 combine with each other to form a substituted or unsubstituted benzene ring.
본 명세서의 일 실시상태에 있어서, R1 및 R2는 서로 결합하여, 벤젠고리를 형성한다. In one embodiment of the present specification, R1 and R2 combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 있어서, 상기 X1은 N이다. In one embodiment of the present specification, X1 is N.
또 하나의 실시상태에 있어서, 상기 X2는 CR2이다. In another exemplary embodiment, X2 is CR2.
본 명세서의 일 실시상태에 있어서, 상기 R7 및 R8은 서로 결합하여, 탄화수소 고리를 형성한다. In one embodiment of the present specification, R7 and R8 combine with each other to form a hydrocarbon ring.
본 명세서의 일 실시상태에 있어서, 상기 R7 및 R8은 서로 결합하여, 벤젠 고리를 형성한다. In one embodiment of the present specification, R7 and R8 combine with each other to form a benzene ring.
본 명세서의 일 실시상태에 있어서, 상기 R5 및 R6는 서로 결합하여, 탄화수소 고리를 형성한다. In one embodiment of the present specification, R5 and R6 combine with each other to form a hydrocarbon ring.
또 하나의 실시상태에 있어서, 상기 R5 및 R6는 서로 결합하여, 벤젠 고리를 형성한다. In another exemplary embodiment, R5 and R6 combine with each other to form a benzene ring.
본 명세서에서 상기 벤젠고리나 탄화수소고리는 치환 또는 비치환될 수 있다. In the present specification, the benzene ring or hydrocarbon ring may be substituted or unsubstituted.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 헤테로환 화합물은 하기 화학식 1A 또는 화학식 1B로 표시된다. In one embodiment of the present specification, the heterocyclic compound represented by Formula 1 is represented by the following Formula 1A or Formula 1B.
[화학식 1A][Formula 1A]
Figure PCTKR2015007418-appb-I000002
Figure PCTKR2015007418-appb-I000002
[화학식 1B][Formula 1B]
Figure PCTKR2015007418-appb-I000003
Figure PCTKR2015007418-appb-I000003
화학식 1A 및 화학식 1B에 있어서, In Formula 1A and Formula 1B,
Y1 내지 Y4, Z1 내지 Z4 및 R2는 화학식 1에서 정의한 바와 동일하고, Y1 to Y4, Z1 to Z4 and R2 are the same as defined in Formula 1,
X3 내지 X6은 서로 동일하거나 상이하고, 각각 독립적으로 CR3 또는 N이며, X3 to X6 are the same as or different from each other, and each independently CR3 or N,
R3는 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기; 또는 치환 또는 비치환된 포스핀옥사이드기이거나, 인접하는 치환기는 서로 결합하여 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리를 형성한다.Each R 3 is independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or a substituted or unsubstituted phosphine oxide group, or adjacent substituents are bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heteroring.
본 명세서의 일 실시상태에 있어서, Y1은 CR5이다. In one embodiment of the present specification, Y1 is CR5.
또 하나의 실시상태에 있어서, 상기 Y2는 CR6이다. In another exemplary embodiment, Y2 is CR6.
또 다른 실시상태에 있어서, 상기 Y3는 CR7이다. In another embodiment, Y3 is CR7.
본 명세서의 일 실시상태에 있어서, 상기 Y4는 CR8이다.In one embodiment of the present specification, Y4 is CR8.
본 명세서의 일 실시상태에 있어서, 상기 Z1는 CR9이다. In one embodiment of the present specification, Z1 is CR9.
또 하나의 실시상태에 있어서, 상기 Z2는 CR10이다. In another exemplary embodiment, Z2 is CR10.
본 명세서의 일 실시상태에 있어서, 상기 Z3는 CR11이다. In one embodiment of the present specification, Z3 is CR11.
본 명세서의 하나의 실시상태에 있어서, 상기 Z4는 CR12이다. In one embodiment of the present specification, Z4 is CR12.
본 명세서의 일 실시상태에 있어서, 상기 X3 내지 X6은 각각 CR3이다. In one embodiment of the present specification, X3 to X6 are each CR3.
본 명세서의 하나의 실시상태에 있어서, 상기 X3 내지 X6의 각 CR3는 서로 동일하거나 상이할 수 있다. In one embodiment of the present specification, each CR3 of the X3 to X6 may be the same or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 헤테로환 화합물은 하기 화학식 1-1 내지 1-4 중 어느 하나로 표시된다. In one embodiment of the present specification, the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-4.
[화학식 1-1][Formula 1-1]
Figure PCTKR2015007418-appb-I000004
Figure PCTKR2015007418-appb-I000004
[화학식 1-2][Formula 1-2]
Figure PCTKR2015007418-appb-I000005
Figure PCTKR2015007418-appb-I000005
[화학식 1-3][Formula 1-3]
Figure PCTKR2015007418-appb-I000006
Figure PCTKR2015007418-appb-I000006
[화학식 1-4][Formula 1-4]
Figure PCTKR2015007418-appb-I000007
Figure PCTKR2015007418-appb-I000007
화학식 1-1 내지 1-4 에 있어서, In Chemical Formulas 1-1 to 1-4,
a, b 및 c는 각각 1 내지 4의 정수이고, a, b and c are each an integer of 1 to 4,
d 및 e는 각각 1 내지 6의 정수이며, d and e are each an integer of 1 to 6,
a, b, c, d 및 e 가 각각 2 이상의 정수인 경우, 각각의 2 이상의 괄호 내의 구조는 서로 동일하거나 상이하고, when a, b, c, d and e are each an integer of 2 or more, the structures in each of the two or more parentheses are the same or different from each other,
A1 내지 A5 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기; 또는 치환 또는 비치환된 포스핀옥사이드기이다. A1 to A5 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or a substituted or unsubstituted phosphine oxide group.
본 명세서의 일 실시상태에 있어서, 상기 R1, R2 및 R5 내지 R12 중 적어도 하나는 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 아릴기; 또는 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 포스핀옥사이드기이거나, 인접하는 치환기는 서로 결합하여 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 탄화수소고리를 형성한다. In one embodiment of the present specification, at least one of R1, R2, and R5 to R12 is substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group or Unsubstituted aryl group; Or a phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group, or adjacent substituents are bonded to each other to form a cyano group, an aryl A hydrocarbon ring substituted or unsubstituted with one or two or more substituents selected from the group consisting of a group, a heterocyclic group and a phosphine oxide group is formed.
본 명세서의 일 실시상태에 있어서, R1 내지 R3 및 R5 내지 R12 중 적어도 하나는 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 아릴기; 또는 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 포스핀옥사이드기이거나, 인접하는 치환기는 서로 결합하여 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 벤젠고리를 형성한다. In one embodiment of the present specification, at least one of R1 to R3 and R5 to R12 is substituted or unsubstituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group Ring aryl group; Or a phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group, or adjacent substituents are bonded to each other to form a cyano group, an aryl A benzene ring unsubstituted or substituted with one or two or more substituents selected from the group consisting of a group, a heterocyclic group and a phosphine oxide group is formed.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R3 및 R5 내지 R12는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 아릴기; 또는 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 포스핀옥사이드기이거나, 인접하는 치환기는 서로 결합하여 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 벤젠고리를 형성한다. In one embodiment of the present specification, R1 to R3 and R5 to R12 are the same as or different from each other, and each independently hydrogen; An aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group; Or a phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group, or adjacent substituents are bonded to each other to form a cyano group, an aryl A benzene ring unsubstituted or substituted with one or two or more substituents selected from the group consisting of a group, a heterocyclic group and a phosphine oxide group is formed.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R3 및 R5 내지 R12는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 피리딘기로 치환된 페닐기; 퀴놀린기로 치환된 페닐기; 파이렌기로 치환된 페닐기; 나프틸기로 치환된 페닐기로 치환된 나프틸기; 페난트레닐기로 치환된 나프틸기; 화학식 1B 및 페닐기로 이루어진 군에서 선택되는 치환기로 1 또는 2 이상이 치환된 플루오레닐기; 시아노기로 치환된 페닐기로 치환된 나프틸기; 나프틸기로 치환된 안트라센기로 치환된 페닐기; 아릴기로 치환된 포스핀옥사이드기로 치환된 나프틸기; 나프틸기로 치환된 포스핀옥사이드기; 나프틸기; 나프틸기로 치환된 페닐기; 바이페닐기; 터페닐기; 트리페닐렌기; 페닐기로 치환된 나프틸기; 또는 페난트레닐기이거나, 인접하는 치환기는 서로 결합하여, 피리딘기로 치환된 페닐기; 퀴놀린기로 치환된 페닐기; 파이렌기로 치환된 페닐기; 나프틸기로 치환된 페닐기로 치환된 나프틸기; 페난트레닐기로 치환된 나프틸기; 화학식 1B 및 페닐기로 이루어진 군에서 선택되는 치환기로 1 또는 2 이상이 치환된 플루오레닐기; 시아노기로 치환된 페닐기로 치환된 나프틸기; 나프틸기로 치환된 안트라센기로 치환된 페닐기; 아릴기로 치환된 포스핀옥사이드기로 치환된 나프틸기; 나프틸기로 치환된 포스핀옥사이드기; 나프틸기; 나프틸기로 치환된 페닐기; 바이페닐기; 터페닐기; 트리페닐렌기; 페닐기로 치환된 나프틸기; 및 페난트레닐기로 이루어진 군에서 선택되는 치환기로 치환 또는 비치환된 벤젠고리를 형성한다. In one embodiment of the present specification, R1 to R3 and R5 to R12 are the same as or different from each other, and each independently hydrogen; A phenyl group substituted with a pyridine group; A phenyl group substituted with a quinoline group; Phenyl group substituted with pyrene group; A naphthyl group substituted with a phenyl group substituted with a naphthyl group; Naphthyl group substituted with phenanthrenyl group; A fluorenyl group substituted with one or two or more substituents selected from the group consisting of Formula 1B and a phenyl group; A naphthyl group substituted with a phenyl group substituted with a cyano group; A phenyl group substituted with an anthracene group substituted with a naphthyl group; A naphthyl group substituted with a phosphine oxide group substituted with an aryl group; Phosphine oxide groups substituted with naphthyl groups; Naphthyl group; Phenyl group substituted with naphthyl group; Biphenyl group; Terphenyl group; Triphenylene group; Naphthyl group substituted with phenyl group; Or a phenanthrenyl group, or adjacent substituents are bonded to each other and substituted with a pyridine group; A phenyl group substituted with a quinoline group; Phenyl group substituted with pyrene group; A naphthyl group substituted with a phenyl group substituted with a naphthyl group; Naphthyl group substituted with phenanthrenyl group; A fluorenyl group substituted with one or two or more substituents selected from the group consisting of Formula 1B and a phenyl group; A naphthyl group substituted with a phenyl group substituted with a cyano group; A phenyl group substituted with an anthracene group substituted with a naphthyl group; A naphthyl group substituted with a phosphine oxide group substituted with an aryl group; Phosphine oxide groups substituted with naphthyl groups; Naphthyl group; Phenyl group substituted with naphthyl group; Biphenyl group; Terphenyl group; Triphenylene group; Naphthyl group substituted with phenyl group; And a phenyl ring unsubstituted or substituted with a substituent selected from the group consisting of phenanthrenyl groups.
본 명세서의 일 실시상태에 있어서, 상기 R1은 수소이다. In one embodiment of the present specification, R1 is hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 R2는 수소이다.In one embodiment of the present specification, R2 is hydrogen.
또 하나의 실시상태에 있어서, 상기 R2는 치환 또는 비치환된 아릴기이다.In another exemplary embodiment, R2 is a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 있어서, 상기 R2는 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 아릴기이다. In one embodiment of the present specification, R2 is an aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
본 명세서의 일 실시상태에 있어서, 상기 R2는 치환 또는 비치환된 아릴기로 치환된 아릴기이다. In one embodiment of the present specification, R2 is an aryl group which is substituted with a substituted or unsubstituted aryl group.
또 하나의 실시상태에 있어서, 상기 R2는 파이렌기로 치환된 아릴기이다. In another exemplary embodiment, R2 is an aryl group which is substituted with a pyrene group.
또 하나의 실시상태에 있어서, 상기 R2는 치환 또는 비치환된 아릴기로 치환된 페닐기이다. In another exemplary embodiment, R2 is a phenyl group substituted with a substituted or unsubstituted aryl group.
또 다른 실시상태에 있어서, 상기 R2는 파이렌기로 치환된 페닐기이다. In another embodiment, R2 is a phenyl group substituted with a pyrene group.
또 다른 실시상태에 있어서, 상기 R2는 치환 또는 비치환된 안트라센기로 치환된 페닐기이다. In another embodiment, R2 is a phenyl group substituted with a substituted or unsubstituted anthracene group.
또 하나의 실시상태에 있어서, 상기 R2는 나프틸기로 치환된 안트라센기로 치환된 페닐기이다. In another exemplary embodiment, R2 is a phenyl group substituted with an anthracene group substituted with a naphthyl group.
또 하나의 실시상태에 있어서, 상기 R2는 치환 또는 비치환된 아릴기로 치환된 나프틸기이다. In another exemplary embodiment, R2 is a naphthyl group which is substituted with a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 있어서, 상기 R2는 페난트레닐기로 치환된 나프틸기이다. In one embodiment of the present specification, R2 is a naphthyl group substituted with a phenanthrenyl group.
또 하나의 실시상태에 있어서, 상기 R2는 치환 또는 비치환된 페닐기로 치환된 나프틸기이다. In another exemplary embodiment, R2 is a naphthyl group which is substituted with a substituted or unsubstituted phenyl group.
또 하나의 실시상태에 있어서, 상기 R2는 시아노기로 치환된 페닐기로 치환된 나프틸기이다.In another exemplary embodiment, R2 is a naphthyl group substituted with a phenyl group substituted with a cyano group.
또 다른 실시상태에 있어서, 상기 R2는 나프틸기로 치환된 페닐기로 치환된 나프틸기이다. In another exemplary embodiment, R2 is a naphthyl group substituted with a phenyl group substituted with a naphthyl group.
본 명세서의 일 실시상태에 있어서, 상기 R2는 치환 또는 비치환된 화학식 1B로 치환된 화학식 1B 및 페닐기로 이루어진 군에서 선택되는 치환기로 1 또는 2 이상이 치환된 플루오레닐기이다. In one embodiment of the present specification, R2 is a fluorenyl group which is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted Formula 1B and a phenyl group.
또 다른 실시상태에 있어서, 상기 R2는 화학식 1B 및 나프틸기로 치환된 플루오레닐기이다. In another exemplary embodiment, R2 is a fluorenyl group substituted with Formula 1B and a naphthyl group.
본 명세서의 일 실시상태에 있어서, 상기 R3는 수소이다. In one embodiment of the present specification, R3 is hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 R3는 치환 또는 비치환된 아릴기이다. In one embodiment of the present specification, R3 is a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 있어서, 상기 R3는 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 포스핀옥사이드기이다.In one embodiment of the present specification, R3 is a phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
또 하나의 실시상태에 있어서, 상기 R3는 아릴기로 치환된 아릴기이다. In another exemplary embodiment, R3 is an aryl group which is substituted with an aryl group.
본 명세서의 일 실시상태에 있어서, 상기 R3는 나프틸기로 치환된 아릴기이다. In one embodiment of the present specification, R3 is an aryl group which is substituted with a naphthyl group.
또 다른 실시상태에 있어서, 상기 R3는 나프틸기로 치환된 페닐기이다. In another exemplary embodiment, R3 is a phenyl group substituted with a naphthyl group.
본 명세서의 일 실시상태에 있어서, 상기 R3는 페닐기로 치환된 아릴기이다.In one embodiment of the present specification, R3 is an aryl group which is substituted with a phenyl group.
본 명세서의 일 실시상태에 있어서, 상기 R3는 아릴기로 치환된 페닐기이다.In one embodiment of the present specification, R3 is a phenyl group substituted with an aryl group.
본 명세서의 다른 실시상태에 있어서, 상기 R3는 아릴기로 치환된 나프틸기이다.In another embodiment of the present specification, R3 is a naphthyl group which is substituted with an aryl group.
또 하나의 실시상태에 있어서, 상기 R3는 페닐기로 치환된 페닐기이다. In another exemplary embodiment, R3 is a phenyl group substituted with a phenyl group.
또 다른 실시상태에 있어서, 상기 R3는 페닐기로 치환된 나프틸기이다.In another exemplary embodiment, R3 is a naphthyl group which is substituted with a phenyl group.
본 명세서의 일 실시상태에 있어서, 상기 R3는 비치환된 아릴기이다.In one embodiment of the present specification, R3 is an unsubstituted aryl group.
하나의 실시상태에 있어서, 상기 R3는 나프틸기이다. In one embodiment, R3 is a naphthyl group.
또 하나의 실시상태에 있어서, 상기 R3는 페난트레닐기이다.In another exemplary embodiment, R3 is a phenanthrenyl group.
다른 실시상태에 있어서, 상기 R3는 터페닐기이다.In another embodiment, R3 is a terphenyl group.
또 하나의 실시상태에 있어서, 상기 R3는 트리페닐렌기이다.In another exemplary embodiment, R3 is a triphenylene group.
또 다른 실시상태에 있어서, 상기 R3는 바이페닐기이다.In another embodiment, R3 is a biphenyl group.
하나의 실시상태에 있어서, 상기 R3는 헤테로고리기로 치환된 아릴기이다.In one embodiment, R3 is an aryl group substituted with a heterocyclic group.
또 하나의 실시상태에 있어서, 상기 R3는 피리딘기로 치환된 아릴기이다.In another exemplary embodiment, R3 is an aryl group which is substituted with a pyridine group.
또 다른 실시상태에 있어서, 상기 R3는 피리딘기로 치환된 페닐기이다.In another embodiment, R3 is a phenyl group substituted with a pyridine group.
하나의 실시상태에 있어서, 상기 R3는 포스핀옥사이드기로 치환된 아릴기이다.In one embodiment, R3 is an aryl group substituted with a phosphine oxide group.
하나의 실시상태에 있어서, 상기 R3는 포스핀옥사이드기로 치환된 나프틸기이다.In one embodiment, R3 is a naphthyl group substituted with a phosphine oxide group.
하나의 실시상태에 있어서, 상기 R3는 아릴기로 치환된 포스핀옥사이드기로 치환된 나프틸기이다. In one embodiment, R3 is a naphthyl group substituted with a phosphine oxide group substituted with an aryl group.
하나의 실시상태에 있어서, 상기 R3는 페닐기로 치환된 포스핀옥사이드기로 치환된 나프틸기이다. In one embodiment, R3 is a naphthyl group substituted with a phosphine oxide group substituted with a phenyl group.
또 하나의 실시상태에 있어서, 상기 R3는 아릴기로 치환된 포스핀옥사이드기이다. In another exemplary embodiment, R3 is a phosphine oxide group substituted with an aryl group.
본 명세서의 일 실시상태에 있어서, 상기 R3는 나프틸기로 치환된 포스핀옥사이드기이다. In one embodiment of the present specification, R3 is a phosphine oxide group substituted with a naphthyl group.
본 명세서의 일 실시상태에 있어서, 상기 R5는 수소이다. In one embodiment of the present specification, R5 is hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 R6는 수소이다.In one embodiment of the present specification, R6 is hydrogen.
또 하나의 실시상태에 있어서, 상기 R6는 치환 또는 비치환된 아릴기이다.In another exemplary embodiment, R6 is a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 있어서, 상기 R6는 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 아릴기이다. In one embodiment of the present specification, R6 is an aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
하나의 실시상태에 있어서, 상기 R6는 헤테로고리기로 치환된 아릴기이다.In one embodiment, R6 is an aryl group substituted with a heterocyclic group.
또 하나의 실시상태에 있어서, 상기 R6는 피리딘기로 치환된 아릴기이다.In another exemplary embodiment, R6 is an aryl group which is substituted with a pyridine group.
또 다른 실시상태에 있어서, 상기 R6는 피리딘기로 치환된 페닐기이다.In another exemplary embodiment, R6 is a phenyl group substituted with a pyridine group.
본 명세서의 일 실시상태에 있어서, 상기 R7은 수소이다. In one embodiment of the present specification, R7 is hydrogen.
하나의 실시상태에 있어서, 상기 R7은 포스핀옥사이드기로 치환된 아릴기이다.In one embodiment, R7 is an aryl group substituted with a phosphine oxide group.
하나의 실시상태에 있어서, 상기 R7은 포스핀옥사이드기로 치환된 나프틸기이다.In one embodiment, R7 is a naphthyl group substituted with a phosphine oxide group.
하나의 실시상태에 있어서, 상기 R7은 아릴기로 치환된 포스핀옥사이드기로 치환된 나프틸기이다. In one embodiment, R7 is a naphthyl group substituted with a phosphine oxide group substituted with an aryl group.
하나의 실시상태에 있어서, 상기 R7은 페닐기로 치환된 포스핀옥사이드기로 치환된 나프틸기이다. In one embodiment, R7 is a naphthyl group substituted with a phosphine oxide group substituted with a phenyl group.
또 하나의 실시상태에 있어서, 상기 R7은 치환 또는 비치환된 아릴기이다.In another exemplary embodiment, R7 is a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 있어서, 상기 R7은 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 아릴기이다. In one embodiment of the present specification, R7 is an aryl group which is unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
하나의 실시상태에 있어서, 상기 R7은 헤테로고리기로 치환된 아릴기이다.In one embodiment, R7 is an aryl group substituted with a heterocyclic group.
또 하나의 실시상태에 있어서, 상기 R7은 퀴놀린기로 치환된 아릴기이다.In another exemplary embodiment, R7 is an aryl group which is substituted with a quinoline group.
또 다른 실시상태에 있어서, 상기 R7은 퀴놀린기로 치환된 페닐기이다.In another embodiment, R7 is a phenyl group substituted with a quinoline group.
본 명세서의 일 실시상태에 있어서, 상기 R8은 수소이다.In one embodiment of the present specification, R8 is hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 R9는 수소이다. In one embodiment of the present specification, R9 is hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 R10은 수소이다.In one embodiment of the present specification, R10 is hydrogen.
또 하나의 실시상태에 있어서, 상기 R10은 치환 또는 비치환된 아릴기이다.In another exemplary embodiment, R10 is a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 있어서, 상기 R10은 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 아릴기이다. In one embodiment of the present specification, R10 is an aryl group which is unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
하나의 실시상태에 있어서, 상기 R10은 헤테로고리기로 치환된 아릴기이다.In one embodiment, R10 is an aryl group substituted with a heterocyclic group.
또 하나의 실시상태에 있어서, 상기 R10은 퀴놀린기로 치환된 아릴기이다.In another exemplary embodiment, R10 is an aryl group which is substituted with a quinoline group.
또 다른 실시상태에 있어서, 상기 R10은 퀴놀린기로 치환된 페닐기이다.In another embodiment, R10 is a phenyl group substituted with a quinoline group.
본 명세서의 일 실시상태에 있어서, 상기 R11은 수소이다. In one embodiment of the present specification, R11 is hydrogen.
본 명세서의 일 실시상태에 있어서, 상기 R12는 수소이다.In one embodiment of the present specification, R12 is hydrogen.
본 명세서의 일 실시상태에 있어서, A1 내지 A3 중 적어도 하나는 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 아릴기; 또는 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 포스핀옥사이드기이다. In one embodiment of the present specification, at least one of A1 to A3 is an aryl group which is unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group ; Or a phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
본 명세서의 일 실시상태에 있어서, 상기 A1 내지 A5는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 아릴기; 또는 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 포스핀옥사이드기이다.In one embodiment of the present specification, A1 to A5 are the same as or different from each other, and each independently hydrogen; An aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group; Or a phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group.
본 명세서의 일 실시상태에 있어서, 상기 A1 내지 A5는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 피리딘기로 치환된 페닐기; 퀴놀린기로 치환된 페닐기; 파이렌기로 치환된 페닐기; 나프틸기로 치환된 페닐기로 치환된 나프틸기; 페난트레닐기로 치환된 나프틸기; 화학식 1B 및 페닐기로 이루어진 군에서 선택되는 치환기로 1 또는 2 이상이 치환된 플루오레닐기; 시아노기로 치환된 페닐기로 치환된 나프틸기; 나프틸기로 치환된 안트라센기로 치환된 페닐기; 아릴기로 치환된 포스핀옥사이드기로 치환된 나프틸기; 나프틸기로 치환된 포스핀옥사이드기; 나프틸기; 나프틸기로 치환된 페닐기; 바이페닐기; 터페닐기; 트리페닐렌기; 페닐기로 치환된 나프틸기; 또는 페난트레닐기이다.In one embodiment of the present specification, A1 to A5 are the same as or different from each other, and each independently hydrogen; A phenyl group substituted with a pyridine group; A phenyl group substituted with a quinoline group; Phenyl group substituted with pyrene group; A naphthyl group substituted with a phenyl group substituted with a naphthyl group; Naphthyl group substituted with phenanthrenyl group; A fluorenyl group substituted with one or two or more substituents selected from the group consisting of Formula 1B and a phenyl group; A naphthyl group substituted with a phenyl group substituted with a cyano group; A phenyl group substituted with an anthracene group substituted with a naphthyl group; A naphthyl group substituted with a phosphine oxide group substituted with an aryl group; Phosphine oxide groups substituted with naphthyl groups; Naphthyl group; Phenyl group substituted with naphthyl group; Biphenyl group; Terphenyl group; Triphenylene group; Naphthyl group substituted with phenyl group; Or a phenanthrenyl group.
본 명세서의 일 실시상태에 있어서, 상기 R1 내지 R3 및 R5 내지 R12 중 적어도 하나는 하기 구조 중에서 선택된다. In one embodiment of the present specification, at least one of the R1 to R3 and R5 to R12 is selected from the following structure.
Figure PCTKR2015007418-appb-I000008
Figure PCTKR2015007418-appb-I000008
본 명세서의 일 실시상태에 있어서, 상기 A1 내지 A5 중 적어도 하나는 상기 구조 중에서 선택될 수 있다. In one embodiment of the present specification, at least one of A1 to A5 may be selected from the structures.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 헤테로환 화합물은 하기 화학식 1-1-1 내지 1-1-7 중 어느 하나로 표시된다. In one embodiment of the present specification, the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1-1 to 1-1-7.
Figure PCTKR2015007418-appb-I000009
Figure PCTKR2015007418-appb-I000009
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 헤테로환 화합물은 하기 화학식 1-2-1 내지 1-2-10 중 어느 하나로 표시된다. In one embodiment of the present specification, the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-2-1 to 1-2-10.
Figure PCTKR2015007418-appb-I000010
Figure PCTKR2015007418-appb-I000010
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 헤테로환 화합물은 하기 화학식 1-3-1 내지 1-3-5 중 어느 하나로 표시된다.In one embodiment of the present specification, the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-3-1 to 1-3-5.
Figure PCTKR2015007418-appb-I000011
Figure PCTKR2015007418-appb-I000011
본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 헤테로환 화합물은 하기 화학식 1-4-1 내지 1-4-7 중 어느 하나로 표시된다.In one embodiment of the present specification, the heterocyclic compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-4-1 to 1-4-7.
Figure PCTKR2015007418-appb-I000012
Figure PCTKR2015007418-appb-I000012
본 명세서의 일 실시상태에 있어서, 상기 전자수송층은 하기 화학식 2로 표시되는 방향족 헤테로고리를 함유하는 유기 화합물을 포함한다. In one embodiment of the present specification, the electron transport layer includes an organic compound containing an aromatic hetero ring represented by the following formula (2).
[화학식 2][Formula 2]
Figure PCTKR2015007418-appb-I000013
Figure PCTKR2015007418-appb-I000013
화학식 2에 있어서, In Chemical Formula 2,
X5 및 X6은 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 CH 이고, X5 and X6 are the same as or different from each other, and each independently N or CH,
Ar1 내지 Ar3는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이다. Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 하나의 실시상태에 있어서, Ar1 내지 Ar3 중 적어도 하나는 하기 화학식 3으로 표시된다.In one embodiment of the present specification, at least one of Ar1 to Ar3 is represented by the following formula (3).
[화학식 3][Formula 3]
Figure PCTKR2015007418-appb-I000014
Figure PCTKR2015007418-appb-I000014
화학식 3에 있어서, In Chemical Formula 3,
o, p 및 q는 0 또는 1이고, o, p and q are 0 or 1,
1 ≤ o + p + q ≤ 3 이며, 1 ≤ o + p + q ≤ 3,
r은 1 또는 2이고, r is 1 or 2,
r이 2 인 경우, 2개의 Ar은 서로 동일하거나 상이하며, when r is 2, two Ar are the same as or different from each other,
L1 내지 L3는 서로 동일하거나 상이하고, 각각 독립적으로 페닐렌기; 또는 나프탈렌기; 또는 플루오레닐렌기이고, L1 to L3 are the same as or different from each other, and each independently a phenylene group; Or naphthalene group; Or a fluorenylene group,
Ar은 아릴기 및 헤테로고리기로 이루어진 군에서 선택되는 1 또는 2 이상의 치환기로 치환 또는 비치환된 아릴기; 또는 아릴기 및 헤테로고리기로 이루어진 군에서 선택되는 1 또는 2 이상의 치환기로 치환 또는 비치환된 헤테로고리기이다. Ar is an aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group; Or a heterocyclic group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group.
본 명세서의 일 실시상태에 있어서, o는 1이다.In one embodiment of the present specification, o is 1.
또 다른 실시상태에 있어서, 상기 o는 0이다.In another embodiment, o is zero.
본 명세서의 일 실시상태에 있어서, 상기 p는 0이다.In one embodiment of the present specification, p is 0.
또 하나의 실시상태에 있어서, 상기 p는 1이다. In another embodiment, p is 1.
본 명세서의 일 실시상태에 있어서, 상기 q는 0이다.In one embodiment of the present specification, q is 0.
또 다른 실시상태에 있어서, 상기 q는 1이다. In another embodiment, q is one.
본 명세서의 일 실시상태에 있어서, 상기 r은 1이다.In one embodiment of the present specification, r is 1.
또 다른 실시상태에 있어서, 상기 r은 2이다. In another embodiment, r is two.
본 명세서의 일 실시상태에 있어서, 상기 L1은 페닐렌기이다. In one embodiment of the present specification, L1 is a phenylene group.
또 하나의 실시상태에 있어서, 상기 L1은 나프탈렌기이다. In another exemplary embodiment, L1 is a naphthalene group.
또 하나의 실시상태에 있어서, 상기 L1은 플루오레닐렌기이다. In another exemplary embodiment, L1 is a fluorenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L2는 페닐렌기이다. In one embodiment of the present specification, L2 is a phenylene group.
또 하나의 실시상태에 있어서, 상기 L2는 나프탈렌기이다. In another exemplary embodiment, L2 is a naphthalene group.
또 하나의 실시상태에 있어서, 상기 L2는 플루오레닐렌기이다. In another exemplary embodiment, L2 is a fluorenylene group.
본 명세서의 일 실시상태에 있어서, 상기 L3는 페닐렌기이다. In one embodiment of the present specification, L3 is a phenylene group.
또 하나의 실시상태에 있어서, 상기 L3는 나프탈렌기이다. In another exemplary embodiment, L3 is a naphthalene group.
또 하나의 실시상태에 있어서, 상기 L3는 플루오레닐렌기이다. In another exemplary embodiment, L3 is a fluorenylene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar은 아릴기 및 헤테로고리기로 이루어진 군에서 선택되는 1 또는 2 이상의 치환기로 치환 또는 비치환된 아릴기; 또는 아릴기 및 헤테로고리기로 이루어진 군에서 선택되는 1 또는 2 이상의 치환기로 치환 또는 비치환된 헤테로고리기이다. In one embodiment of the present specification, Ar is an aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group; Or a heterocyclic group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group.
하나의 실시상태에 있어서, 상기 Ar은 아릴기 및 헤테로고리기로 이루어진 군에서 선택되는 1 또는 2 이상의 치환기로 치환 또는 비치환된 헤테로고리기이다. In one embodiment, Ar is a heterocyclic group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group.
또 하나의 실시상태에 있어서, 상기 Ar은 퀴놀린기이다. In another exemplary embodiment, Ar is a quinoline group.
본 명세서의 일 실시상태에 있어서, 상기 Ar은 아릴기로 치환 또는 비치환된 헤테로고리기이다.In one embodiment of the present specification, Ar is a heterocyclic group unsubstituted or substituted with an aryl group.
또 하나의 실시상태에 있어서, 상기 Ar은 페닐기로 치환 또는 비치환된 헤테로고리기이다.In another exemplary embodiment, Ar is a heterocyclic group which is unsubstituted or substituted with a phenyl group.
또 다른 실시상태에 있어서, 상기 Ar은 페닐기로 치환된 피리미딘기이다. In another exemplary embodiment, Ar is a pyrimidine group substituted with a phenyl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar은 페닐기로 치환된 피리딘기이다. In one embodiment of the present specification, Ar is a pyridine group substituted with a phenyl group.
또 다른 실시상태에 있어서, 상기 Ar은 페닐기로 치환된 트리아진기이다.In another exemplary embodiment, Ar is a triazine group substituted with a phenyl group.
본 명세서의 다른 실시상태에 있어서, 상기 Ar은 피리딘기이다. In another embodiment of the present specification, Ar is a pyridine group.
본 명세서의 다른 실시상태에 있어서, 상기 Ar은 카바졸기이다. In another embodiment of the present specification, Ar is a carbazole group.
본 명세서의 하나의 실시상태에 있어서, 상기 Ar은 아릴기 및 헤테로고리기로 이루어진 군에서 선택되는 1 또는 2 이상의 치환기로 치환 또는 비치환된 아릴기이다.In one embodiment of the present specification, Ar is an aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group.
본 명세서의 일 실시상태에 있어서, 상기 Ar은 페닐기이다. In one embodiment of the present specification, Ar is a phenyl group.
본 명세서의 다른 실시상태에 있어서, 상기 Ar은 아릴기로 치환된 아릴기이다.In another embodiment of the present specification, Ar is an aryl group which is substituted with an aryl group.
또 하나의 실시상태에 있어서, 상기 Ar은 페닐기로 치환된 아릴기이다.In another exemplary embodiment, Ar is an aryl group which is substituted with a phenyl group.
또 다른 실시상태에 있어서, 상기 Ar은 페닐기로 치환된 플루오레닐기이다.In another exemplary embodiment, Ar is a fluorenyl group substituted with a phenyl group.
본 명세서의 일 실시상태에 있어서, Ar1 내지 Ar3는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 나프틸기; 또는 치환 또는 비치환된 플루오레닐기이다.In one embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted fluorenyl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar1 내지 Ar3는 서로 동일하거나 상이하고, 각각 독립적으로 페닐; 비페닐; 나프탈렌; 페닐-나프탈렌-페닐-퀴놀린; 페닐-나프탈렌-페닐-피리미딘-페닐; 페닐-나프탈렌-페닐-피리딘-페닐; 페닐-나프탈렌-페닐-피리미딘; 플루오렌-페닐; 페닐-터페닐; 비페닐-페닐; 나프틸-플루오렌-페닐; 페닐-플루오렌-페닐; 비페닐-카바졸; 또는 페닐-나프탈렌-페닐-트리아진-페닐이다. In one embodiment of the present specification, Ar1 to Ar3 are the same as or different from each other, and each independently phenyl; Biphenyl; naphthalene; Phenyl-naphthalene-phenyl-quinoline; Phenyl-naphthalene-phenyl-pyrimidine-phenyl; Phenyl-naphthalene-phenyl-pyridine-phenyl; Phenyl-naphthalene-phenyl-pyrimidine; Fluorene-phenyl; Phenyl-terphenyl; Biphenyl-phenyl; Naphthyl-fluorene-phenyl; Phenyl-fluorene-phenyl; Biphenyl-carbazole; Or phenyl-naphthalene-phenyl-triazine-phenyl.
본 명세서의 일 실시상태에 있어서, 상기 "-나프탈렌-"은 2,7-나프탈렌 또는 1,4-나프탈렌이다. In one embodiment of the present specification, the "-naphthalene-" is 2,7-naphthalene or 1,4-naphthalene.
본 명세서의 하나의 실시상태에 있어서, 상기 화학식 2로 표시되는 방향족 헤테로고리를 함유하는 유기 화합물은 하기 화학식 2-1 내지 2-13 중 어느 하나로 표시된다. In one embodiment of the present specification, the organic compound containing the aromatic hetero ring represented by Chemical Formula 2 is represented by any one of the following Chemical Formulas 2-1 to 2-13.
Figure PCTKR2015007418-appb-I000015
Figure PCTKR2015007418-appb-I000015
Figure PCTKR2015007418-appb-I000016
Figure PCTKR2015007418-appb-I000016
상기 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of the substituents are described below, but are not limited thereto.
상기 "치환"이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 동일하거나 상이할 수 있다.The term "substituted" means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 이미드기; 아미드기; 히드록시기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 바이페닐기일 수 있다. 즉, 바이페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수 있다. As used herein, the term "substituted or unsubstituted" is deuterium; Halogen group; Nitrile group; Nitro group; Imide group; Amide group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents. For example, "a substituent to which two or more substituents are linked" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
본 명세서에 있어서,
Figure PCTKR2015007418-appb-I000017
는 다른 치환기 또는 결합부에 결합되는 부위를 의미한다.In the present specification,
Figure PCTKR2015007418-appb-I000017
Means a site which is bonded to another substituent or binding moiety.
상기 아릴기가 단환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나, 탄소수 6 내지 25인 것이 바람직하다. 구체적으로 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. When the aryl group is a monocyclic aryl group, carbon number is not particularly limited, but preferably 6 to 25 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
상기 아릴기가 다환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나. 탄소수 10 내지 24인 것이 바람직하다. 구체적으로 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트릴기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-24. Specifically, the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
본 명세서에 있어서, 상기 플루오레닐기는 치환될 수 있으며, 인접한 치환기들이 서로 결합하여 고리를 형성할 수 있다. In the present specification, the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
상기 플루오레닐기가 치환되는 경우,
Figure PCTKR2015007418-appb-I000018
등이 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,
Figure PCTKR2015007418-appb-I000018
And so on. However, the present invention is not limited thereto.
본 명세서에 있어서, 헤테로고리기는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 싸이오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 피리딜기, 비피리딜기, 피리미딜기, 트리아진기, 트리아졸기, 아크리딜기, 피리다진기, 피라지닐기, 퀴놀리닐기, 퀴나졸린기, 퀴녹살리닐기, 프탈라지닐기, 피리도 피리미디닐기, 피리도 피라지닐기, 피라지노 피라지닐기, 이소퀴놀린기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤즈이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조싸이오펜기, 디벤조싸이오펜기, 벤조퓨라닐기, 페난쓰롤린기(phenanthroline), 티아졸릴기, 이소옥사졸릴기, 옥사디아졸릴기, 티아디아졸릴기, 벤조티아졸릴기, 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like. Although carbon number is not specifically limited, It is preferable that it is C2-C60. Examples of the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, acridil group , Pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group , Carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline group, thiazolyl group, isoxazolyl Groups, oxadiazolyl groups, thiadiazolyl groups, benzothiazolyl groups, phenothiazinyl groups, dibenzofuranyl groups, and the like, but are not limited thereto.
상기 헤테로고리기는 단환 또는 다환일 수 있으며, 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있다.The heterocyclic group may be monocyclic or polycyclic, and may be aromatic, aliphatic or a condensed ring of aromatic and aliphatic.
본 명세서에 있어서, "인접한" 기는 해당 치환기가 치환된 원자와 직접 연결된 원자에 치환된 치환기, 해당 치환기와 입체구조적으로 가장 가깝게 위치한 치환기, 또는 해당 치환기가 치환된 원자에 치환된 다른 치환기를 의미할 수 있다. 예컨대, 벤젠고리에서 오르토(ortho)위치로 치환된 2개의 치환기 및 지방족 고리에서 동일 탄소에 치환된 2개의 치환기는 서로 "인접한" 기로 해석될 수 있다. As used herein, the term "adjacent" means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an atom to which the substituent is substituted. Can be. For example, two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups.
본 명세서에서 인접하는 기가 서로 결합하여, 탄화수소고리 또는 헤테로고리를 형성하는 것은 인접하는 치환기가 결합을 형성하여, 5원 내지 7원의 단환 또는 다환의 탄화수소고리 또는 5원 내지 7원의 단환 또는 다환의 헤테로고리기를 형성하는 것을 의미한다. In the present specification, the adjacent groups are bonded to each other to form a hydrocarbon ring or a hetero ring, in which the adjacent substituents form a bond, a 5- to 7-membered monocyclic or polycyclic hydrocarbon ring or a 5- to 7-membered monocyclic or multi It means forming the heterocyclic group of the ring.
본 명세서에서 탄화수소고리는 시클로알킬기; 시클로알케닐기; 방향족고리기; 또는 지방족고리기를 모두 포함하며, 단환 또는 다환일 수 있으며, 이들이 1 또는 2 이상이 결합하여 축합된 고리를 모두 포함한다.In the present specification, the hydrocarbon ring is a cycloalkyl group; Cycloalkenyl group; Aromatic ring groups; Or include all aliphatic ring groups, which may be monocyclic or polycyclic, and include all rings condensed by combining one or two or more.
본 명세서에서 형성된 헤테로고리는 상기 탄화수소고리 중 적어도 하나의 탄소원자가 N, O, 또는 S 원자로 치환된 것을 의미하며, 지방족고리 또는 방향족고리일 수 있으며, 단환 또는 다환일 수 있다.Heterocycle formed herein means that at least one carbon atom of the hydrocarbon ring is substituted with N, O, or S atoms, may be an aliphatic ring or an aromatic ring, it may be monocyclic or polycyclic.
본 명세서의 유기 발광 소자는 전자수송층 및 전자조절층을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. The organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except for including an electron transport layer and an electron control layer.
예컨대, 본 명세서의 유기 발광 소자는 기판 상에 애노드, 유기물층 및 캐소드를 순차적으로 적층시킴으로써 제조할 수 있다. 이 때 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 애노드를 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층, 전자조절층 및 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 캐소드로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 캐소드 물질부터 유기물층, 애노드 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. For example, the organic light emitting device of the present specification may be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, the anode is formed by depositing a metal or conductive metal oxide or an alloy thereof on the substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. And an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, an electron adjusting layer, and an electron transporting layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
본 명세서의 유기 발광 소자의 유기물층은 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. The organic material layer of the organic light emitting device of the present specification may have a multilayer structure in which two or more organic material layers are stacked.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 정공주입층, 정공수송층, 전자수송층, 전자주입층, 전자저지층 및 정공저지층으로 이루어진 군에서 선택되는 1 층 또는 2 층 이상을 더 포함할 수 있다. In one embodiment of the present specification, the organic light emitting device further includes one or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer and a hole blocking layer. can do.
예컨대, 본 명세서의 유기 발광 소자의 구조는 도 1에 나타낸 것과 같은 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.For example, the structure of the organic light emitting device of the present specification may have a structure as shown in FIG. 1, but is not limited thereto.
도 1에는 기판(101) 위에 애노드(201), 발광층(301), 전자조절층(401), 전자 수송층(501) 및 캐소드(601)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 상기 도 1은 본 명세서의 실시상태에 따른 예시적인 구조이며, 다른 유기물층을 더 포함할 수 있다. 1 illustrates a structure of an organic light emitting device in which an anode 201, a light emitting layer 301, an electron control layer 401, an electron transport layer 501, and a cathode 601 are sequentially stacked on a substrate 101. 1 is an exemplary structure according to an exemplary embodiment of the present specification, and may further include another organic material layer.
상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 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.
상기 애노드 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 generally 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); ZnO: Al or SNO 2 : Combination of metals and oxides such as 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 캐소드 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. The cathode material is generally 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 주입 물질로는 전극으로부터 정공을 주입하는 층으로, 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과, 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고, 발광층에서 생성된 여기자의 전자주입층 또는 전자주입재료에의 이동을 방지하며, 또한, 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 양극 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 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 한정 되는 것은 아니다. The hole injection material is a layer for injecting holes from an electrode, and the hole injection material has a capability of transporting holes, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in a light emitting layer. The compound which prevents the movement of the excited excitons to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material is 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-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
상기 정공수송층은 정공주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로, 정공 수송 물질로는 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 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 the hole injection layer and transports holes to the light emitting layer. As a hole transport material, the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer. The material is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
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. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 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 thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 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 light emitting layer may include a host material and a dopant material. The host material is a condensed aromatic ring derivative or a heterocyclic 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 containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
도펀트 재료로는 유기 화합물, 금속 또는 금속 화합물이 있다. Dopant materials include organic compounds, metals or metal compounds.
도펀트 재료로서의 유기 화합물로는 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물 등이 있다. 구체적으로 방향족 아민 유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서, 아릴아미노기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있으며, 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 시클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 또는 금속 화합물로는 일반적인 금속 또는 금속 화합물을 사용할 수 있으며, 구체적으로 금속 착체를 사용할 수 있다. 상기 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되지 않는다.Organic compounds as dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds and the like. Specifically, the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted. At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine and the like, but is not limited thereto. In addition, as the metal or the metal compound, a general metal or a metal compound may be used, and specifically, a metal complex may be used. The metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
상기 전자주입층은 전극으로부터 전자를 주입하는 층으로, 전자를 수송하는 능력을 갖고, 음극으로부터의 전자주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공 주입층에의 이동을 방지하고, 또한, 박막형성능력이 우수한 화합물이 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 that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer. The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and 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.
상기 정공저지층은 정공의 음극 도달을 저지하는 층으로, 일반적으로 정공주입층과 동일한 조건으로 형성될 수 있다. 구체적으로 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, BCP, 알루미늄 착물 (aluminum complex) 등이 있으나, 이에 한정되지 않는다. The hole blocking layer is a layer for blocking the arrival of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.
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.
또한, 본 명세서에 따른 유기 발광 소자는 하부 전극이 애노드이고 상부전극이 캐소드인 정구조(normal type)일 수 있고, 하부전극이 캐소드이고 상부전극이 애노드인 역구조(inverted type)일 수도 있다.In addition, the organic light emitting diode according to the present disclosure may be a normal type in which the lower electrode is an anode and the upper electrode is a cathode, or may be an inverted type in which the lower electrode is a cathode and the upper electrode is an anode.
본 명세서의 일 실시상태에 따른 구조는 유기 태양 전지, 유기 감광체, 유기 트랜지스터 등을 비롯한 유기 전자 소자에서도 유기 발광 소자에 적용되는 것과 유사한 원리로 작용할 수 있다. The structure according to the exemplary embodiment of the present specification may act on a principle similar to that applied to an organic light emitting device in an organic electronic device including an organic solar cell, an organic photoconductor, an organic transistor, and the like.
이하, 본 명세서를 구체적으로 설명하기 위해 실시예를 들어 상세하게 설명하기로 한다. 그러나, 본 명세서에 따른 실시예들은 여러 가지 다른 형태로 변형될 수 있으며, 본 명세서의 범위가 아래에서 상술하는 실시예들에 한정되는 것으로 해석되지 않는다. 본 명세서의 실시예들은 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, the present invention will be described in detail with reference to Examples. However, embodiments according to the present disclosure may be modified in various other forms, and the scope of the present disclosure is not interpreted to be limited to the embodiments described below. The embodiments of the present specification are provided to more fully describe the present specification to those skilled in the art.
<실시예 1> 유기 발광 소자의 제조 Example 1 Fabrication of Organic Light-Emitting Element
ITO (indium tin oxide)가 1,000 Å의 두께로 박막 코팅된 유리 기판(corning 7059 glass)을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이 때, 세제로는 Fischer Co.의 제품을 사용하였으며 증류수로는 Millipore Co. 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후, 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 건식 세정한 후 진공 증착기로 기판을 이송시켰다.A glass substrate (corning 7059 glass) coated with ITO (indium tin oxide) at a thickness of 1,000 에 was placed in distilled water in which detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. was used as a detergent and Millipore Co. was used as distilled water. Secondly 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, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, and the like was dried and then transferred to a plasma cleaner. In addition, the substrate was dry-cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
상기와 같이 준비된 ITO 투명 전극 위에 하기 화학식의 화합물인 헥사니트릴헥사아자트리페닐렌 (hexanitrilehexaazatriphenylene: 이하 HAT라 함)을 500Å의 두께로 열 진공 증착하여 박막을 형성하였다. 이 박막에 의하여 기판과 정공주입층 사이의 계면 특성을 향상시킬 수 있다. 이어서, 상기 박막 위에 하기 화학식 HT-1의 화합물을 400Å의 두께로 증착하여 정공수송층을 형성하고, 그 위에 하기 EB-1의 화합물을 250Å의 두께로 증착하여 전자차단층을 형성하였다. 그 위에 발광층의 호스트로 하기 H1과 도판트로 하기 D1의 화합물을 200 Å 두께로 진공증착하였다. 상기 발광층 위에 상기 화합물 1-1-1을 100Å의 두께로 증착하여 전자조절층을 형성하였고 그 위에 상기 화합물 2-1의 전자수송층물질과 리튬 퀴놀레이트(LiQ, Lithium Quinolate)를 1: 1의 중량비로 진공증착하여 300Å의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자수송층 위에 순차적으로 12Å 두께의 리튬 플루오라이드 (LiF)와 2,000Å 두께의 알루미늄을 증착하여 음극을 형성하였다.Hexanitrilehexaazatriphenylene (hereinafter referred to as HAT), a compound of the following formula, was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a thin film. By this thin film, the interface property between the substrate and the hole injection layer can be improved. Subsequently, a hole transport layer was formed by depositing a compound of Formula HT-1 at a thickness of 400 kPa on the thin film, and an electron blocking layer was formed by depositing a compound of EB-1 at a thickness of 250 kPa thereon. The compound of the following H1 and the following D1 as a host of a light emitting layer was vacuum-deposited at 200 microsecond thickness on it. Compound 1-1-1 was deposited to a thickness of 100 Å on the emission layer to form an electron control layer, and the electron transport layer material of the compound 2-1 and lithium quinolate (LiQ, Lithium Quinolate) were added in a weight ratio of 1: 1. Vacuum deposition was carried out to form an electron injection and transport layer having a thickness of 300 kPa. A cathode was formed by sequentially depositing 12 플루오 thick lithium fluoride (LiF) and 2,000 Å thick aluminum on the electron transport layer.
상기의 과정에서 유기물의 증착속도는 0.3 ~ 0.8 Å/sec로 유지하였다. 또한, 음극의 리튬플루오라이드는 0.3 Å/sec, 알루미늄은 1.5 ~ 2.5 Å/sec의 증착 속도를 유지하였다. 증착시 진공도는 1 ~ 3 × 10-7로 유지하였다.In the above process, the deposition rate of the organic material was maintained at 0.3 ~ 0.8 Å / sec. In addition, the lithium fluoride of the negative electrode maintained a deposition rate of 0.3 kPa / sec and aluminum of 1.5 to 2.5 kPa / sec. During deposition, the degree of vacuum was maintained at 1 to 3 × 10 −7 .
Figure PCTKR2015007418-appb-I000019
Figure PCTKR2015007418-appb-I000019
<< 실시예Example 2> 유기 발광 소자의 제조 2> Fabrication of Organic Light-Emitting Device
상기 실시예 1에서 상기 화합물 2-1 대신 화합물 2-3을 사용한 것을 제외하고, 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다. An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2-3 was used instead of Compound 2-1 in Example 1.
<< 실시예Example 3> 유기 발광 소자의 제조 3> Fabrication of organic light emitting device
상기 실시예 1에서 상기 화합물 2-1 대신 화합물 2-4를 사용한 것을 제외하고, 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2-4 was used instead of Compound 2-1 in Example 1.
<< 실시예Example 4> 유기 발광 소자의 제조 4> Fabrication of organic light emitting device
상기 실시예 1에서 상기 화합물 2-1 대신 화합물 2-7를 사용한 것을 제외하고, 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2-7 was used instead of Compound 2-1 in Example 1.
<< 실시예Example 5> 유기 발광 소자의 제조 5> Fabrication of organic light emitting device
상기 실시예 1에서 상기 화합물 2-1 대신 화합물 2-8을 사용한 것을 제외하고, 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2-8 was used instead of Compound 2-1 in Example 1.
<< 실시예Example 6> 유기 발광 소자의 제조 6> Fabrication of organic light emitting device
상기 실시예 1에서 상기 화합물 2-1 대신 화합물 2-13을 사용한 것을 제외하고, 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 2-13 was used instead of Compound 2-1 in Example 1.
<< 실시예Example 7> 유기 발광 소자의 제조 7> Fabrication of organic light emitting device
상기 실시예 1에서 상기 화합물 1-1-1 대신 화합물 1-2-3를 사용한 것을 제외하고, 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 1-2-3 instead of the compound 1-1-1 in Example 1.
<< 실시예Example 8> 유기 발광 소자의 제조 8> Fabrication of organic light emitting device
상기 실시예 1에서 상기 화합물 1-1-1 대신 화합물 1-2-10을 사용한 것을 제외하고, 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Example 1.
<< 실시예Example 9> 유기 발광 소자의 제조 9> Fabrication of organic light emitting device
상기 실시예 1에서 상기 화합물 1-1-1 대신 화합물 1-3-1를 사용한 것을 제외하고, 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Example 1.
<< 실시예Example 10> 유기 발광 소자의 제조 10> Fabrication of Organic Light Emitting Diode
상기 실시예 1에서 상기 화합물 1-1-1 대신 화합물 1-3-2를 사용한 것을 제외하고, 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Example 1.
<< 실시예Example 11> 유기 발광 소자의 제조 11> Fabrication of organic light emitting device
상기 실시예 1에서 상기 화합물 1-1-1 대신 화합물 1-4-1를 사용한 것을 제외하고, 실시예 1과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 1, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Example 1.
<< 실시예Example 12> 유기 발광 소자의 제조 12> Fabrication of organic light emitting device
상기 실시예 2에서 상기 화합물 1-1-1 대신 화합물 1-2-3를 사용한 것을 제외하고, 실시예 2과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 2 except for using the compound 1-2-3 instead of the compound 1-1-1 in Example 2.
<< 실시예Example 13> 유기 발광 소자의 제조 13> Fabrication of organic light emitting device
상기 실시예 2에서 상기 화합물 1-1-1 대신 화합물 1-2-10을 사용한 것을 제외하고, 실시예 2과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 2, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Example 2.
<< 실시예Example 14> 유기 발광 소자의 제조 14> Fabrication of organic light emitting device
상기 실시예 2에서 상기 화합물 1-1-1 대신 화합물 1-3-1를 사용한 것을 제외하고, 실시예 2과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 2, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Example 2.
<< 실시예Example 15> 유기 발광 소자의 제조 15> Fabrication of organic light emitting device
상기 실시예 2에서 상기 화합물 1-1-1 대신 화합물 1-3-2를 사용한 것을 제외하고, 실시예 2과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 2, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Example 2.
<< 실시예Example 16> 유기 발광 소자의 제조 16> Fabrication of Organic Light-Emitting Device
상기 실시예 2에서 상기 화합물 1-1-1 대신 화합물 1-4-1를 사용한 것을 제외하고, 실시예 2과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 2, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Example 2.
<< 실시예Example 17> 유기 발광 소자의 제조 17> Fabrication of organic light emitting device
상기 실시예 3에서 상기 화합물 1-1-1 대신 화합물 1-2-3를 사용한 것을 제외하고, 실시예 3과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 3 except for using the compound 1-2-3 instead of the compound 1-1-1 in Example 3.
<< 실시예Example 18> 유기 발광 소자의 제조 18> Fabrication of organic light emitting device
상기 실시예 3에서 상기 화합물 1-1-1 대신 화합물 1-2-10을 사용한 것을 제외하고, 실시예 3과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 3, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Example 3.
<< 실시예Example 19> 유기 발광 소자의 제조 19> Fabrication of Organic Light Emitting Diode
상기 실시예 3에서 상기 화합물 1-1-1 대신 화합물 1-3-1를 사용한 것을 제외하고, 실시예 3과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 3, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Example 3.
<< 실시예Example 20> 유기 발광 소자의 제조 20> Fabrication of Organic Light Emitting Diode
상기 실시예 3에서 상기 화합물 1-1-1 대신 화합물 1-3-2를 사용한 것을 제외하고, 실시예 3과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 3 except for using the compound 1-3-2 instead of the compound 1-1-1 in Example 3.
<< 실시예Example 21> 유기 발광 소자의 제조 21> Fabrication of organic light emitting device
상기 실시예 3에서 상기 화합물 1-1-1 대신 화합물 1-4-1를 사용한 것을 제외하고, 실시예 3과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 3 except for using the compound 1-4-1 instead of the compound 1-1-1 in Example 3.
<< 실시예Example 22> 유기 발광 소자의 제조 22> Fabrication of organic light emitting device
상기 실시예 4에서 상기 화합물 1-1-1 대신 화합물 1-2-3를 사용한 것을 제외하고, 실시예 4과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 4 except for using the compound 1-2-3 instead of the compound 1-1-1 in Example 4.
<< 실시예Example 23> 유기 발광 소자의 제조 23> Fabrication of Organic Light-Emitting Device
상기 실시예 4에서 상기 화합물 1-1-1 대신 화합물 1-2-10을 사용한 것을 제외하고, 실시예 4과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 4, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Example 4.
<< 실시예Example 24> 유기 발광 소자의 제조 24> Fabrication of Organic Light-Emitting Device
상기 실시예 4에서 상기 화합물 1-1-1 대신 화합물 1-3-1를 사용한 것을 제외하고, 실시예 4과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 4, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Example 4.
<< 실시예Example 25> 유기 발광 소자의 제조 25> Fabrication of Organic Light-Emitting Device
상기 실시예 4에서 상기 화합물 1-1-1 대신 화합물 1-3-2를 사용한 것을 제외하고, 실시예 4과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 4 except for using the compound 1-3-2 instead of the compound 1-1-1 in Example 4.
<< 실시예Example 26> 유기 발광 소자의 제조 26> Fabrication of Organic Light Emitting Device
상기 실시예 4에서 상기 화합물 1-1-1 대신 화합물 1-4-1를 사용한 것을 제외하고, 실시예 4과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 4, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Example 4.
<< 실시예Example 27> 유기 발광 소자의 제조 27> Fabrication of Organic Light-Emitting Device
상기 실시예 5에서 상기 화합물 1-1-1 대신 화합물 1-2-3를 사용한 것을 제외하고, 실시예 5과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 5 except for using the compound 1-2-3 instead of the compound 1-1-1 in Example 5.
<< 실시예Example 28> 유기 발광 소자의 제조 28> Fabrication of Organic Light-Emitting Device
상기 실시예 5에서 상기 화합물 1-1-1 대신 화합물 1-2-10을 사용한 것을 제외하고, 실시예 5과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 5 except for using the compound 1-2-10 instead of the compound 1-1-1 in Example 5.
<< 실시예Example 29> 유기 발광 소자의 제조 29> Fabrication of Organic Light-Emitting Device
상기 실시예 5에서 상기 화합물 1-1-1 대신 화합물 1-3-1를 사용한 것을 제외하고, 실시예 5과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 5, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Example 5.
<< 실시예Example 30> 유기 발광 소자의 제조 30> Fabrication of Organic Light-Emitting Device
상기 실시예 5에서 상기 화합물 1-1-1 대신 화합물 1-3-2를 사용한 것을 제외하고, 실시예 5과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 5, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Example 5.
<< 실시예Example 31> 유기 발광 소자의 제조 31> Fabrication of Organic Light-Emitting Device
상기 실시예 5에서 상기 화합물 1-1-1 대신 화합물 1-4-1를 사용한 것을 제외하고, 실시예 5과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 5, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Example 5.
<< 실시예Example 32> 유기 발광 소자의 제조 32> Fabrication of Organic Light-Emitting Device
상기 실시예 6에서 상기 화합물 1-1-1 대신 화합물 1-2-3를 사용한 것을 제외하고, 실시예 6과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 6 except for using the compound 1-2-3 instead of the compound 1-1-1 in Example 6.
<< 실시예Example 33> 유기 발광 소자의 제조 33> Fabrication of Organic Light Emitting Diode
상기 실시예 6에서 상기 화합물 1-1-1 대신 화합물 1-2-10을 사용한 것을 제외하고, 실시예 6과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 6, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Example 6.
<< 실시예Example 34> 유기 발광 소자의 제조 34> Fabrication of Organic Light-Emitting Device
상기 실시예 6에서 상기 화합물 1-1-1 대신 화합물 1-3-1를 사용한 것을 제외하고, 실시예 6과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 6 except for using the compound 1-3-1 instead of the compound 1-1-1 in Example 6.
<< 실시예Example 35> 유기 발광 소자의 제조 35> Fabrication of Organic Light-Emitting Device
상기 실시예 6에서 상기 화합물 1-1-1 대신 화합물 1-3-2를 사용한 것을 제외하고, 실시예 6과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 6, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Example 6.
<< 실시예Example 36> 유기 발광 소자의 제조 36> Fabrication of Organic Light-Emitting Device
상기 실시예 6에서 상기 화합물 1-1-1 대신 화합물 1-4-1를 사용한 것을 제외하고, 실시예 6과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Example 6, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Example 6.
<< 비교예Comparative example 1> 유기 발광 소자의 제조 1> Fabrication of organic light emitting device
상기 실시예 1에서 상기 화합물 1-1-1 대신 하기 화학식 ET-1을 사용한 것을 제외하고, 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 following Chemical Formula ET-1 instead of the compound 1-1-1 in Example 1.
[화학식 ET-1][Formula ET-1]
Figure PCTKR2015007418-appb-I000020
Figure PCTKR2015007418-appb-I000020
<< 비교예Comparative example 2> 유기 발광 소자의 제조 2> Fabrication of Organic Light-Emitting Device
상기 실시예 2에서 상기 화합물 1-1-1 대신 하기 화학식 ET-1을 사용한 것을 제외하고, 실시예 2과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 2 except for using the following Chemical Formula ET-1 instead of the compound 1-1-1 in Example 2.
<< 비교예Comparative example 3> 유기 발광 소자의 제조 3> Fabrication of organic light emitting device
상기 실시예 3에서 상기 화합물 1-1-1 대신 하기 화학식 ET-1을 사용한 것을 제외하고, 실시예 3과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 3 except for using the following Chemical Formula ET-1 instead of the compound 1-1-1 in Example 3.
<< 비교예Comparative example 4> 유기 발광 소자의 제조 4> Fabrication of organic light emitting device
상기 실시예 4에서 상기 화합물 1-1-1 대신 하기 화학식 ET-1을 사용한 것을 제외하고, 실시예 4과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 4 except for using the following Chemical Formula ET-1 instead of the compound 1-1-1 in Example 4.
<< 비교예Comparative example 5> 유기 발광 소자의 제조 5> Fabrication of organic light emitting device
상기 실시예 5에서 상기 화합물 1-1-1 대신 하기 화학식 ET-1을 사용한 것을 제외하고, 실시예 5과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 5 except for using the following Chemical Formula ET-1 instead of the compound 1-1-1 in Example 5.
<< 비교예Comparative example 6> 유기 발광 소자의 제조 6> Fabrication of organic light emitting device
상기 실시예 6에서 상기 화합물 1-1-1 대신 하기 화학식 ET-1을 사용한 것을 제외하고, 실시예 6과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 6 except for using the following Chemical Formula ET-1 instead of the compound 1-1-1 in Example 6.
<< 비교예Comparative example 7> 유기 발광 소자의 제조 7> Fabrication of organic light emitting device
상기 실시예 1에서 상기 화합물 1-1-1 대신 하기 화학식 ET-2을 사용한 것을 제외하고, 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 following Chemical Formula ET-2 instead of the compound 1-1-1 in Example 1.
[화학식 ET-2][Formula ET-2]
Figure PCTKR2015007418-appb-I000021
Figure PCTKR2015007418-appb-I000021
<< 비교예Comparative example 8> 유기 발광 소자의 제조 8> Fabrication of organic light emitting device
상기 실시예 2에서 상기 화합물 1-1-1 대신 하기 화학식 ET-2을 사용한 것을 제외하고, 실시예 2과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 2 except for using the following Chemical Formula ET-2 instead of the compound 1-1-1 in Example 2.
<< 비교예Comparative example 9> 유기 발광 소자의 제조 9> Fabrication of organic light emitting device
상기 실시예 3에서 상기 화합물 1-1-1 대신 하기 화학식 ET-2을 사용한 것을 제외하고, 실시예 3과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 3 except for using the following Chemical Formula ET-2 instead of the compound 1-1-1 in Example 3.
<< 비교예Comparative example 10> 유기 발광 소자의 제조 10> Fabrication of Organic Light Emitting Diode
상기 실시예 4에서 상기 화합물 1-1-1 대신 하기 화학식 ET-2을 사용한 것을 제외하고, 실시예 4과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 4 except for using the following Chemical Formula ET-2 instead of the compound 1-1-1 in Example 4.
<< 비교예Comparative example 11> 유기 발광 소자의 제조 11> Fabrication of organic light emitting device
상기 실시예 5에서 상기 화합물 1-1-1 대신 하기 화학식 ET-2을 사용한 것을 제외하고, 실시예 5과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 5 except for using the following Chemical Formula ET-2 instead of the compound 1-1-1 in Example 5.
<< 비교예Comparative example 12> 유기 발광 소자의 제조 12> Fabrication of organic light emitting device
상기 실시예 6에서 상기 화합물 1-1-1 대신 하기 화학식 ET-2을 사용한 것을 제외하고, 실시예 6과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 6 except for using the following Chemical Formula ET-2 instead of the compound 1-1-1 in Example 6.
<< 비교예Comparative example 13> 유기 발광 소자의 제조 13> Fabrication of organic light emitting device
상기 실시예 1에서 상기 화합물 1-1-1 대신 하기 화학식 ET-3을 사용한 것을 제외하고, 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 following Chemical Formula ET-3 instead of the compound 1-1-1 in Example 1.
[화학식 ET-3][Formula ET-3]
Figure PCTKR2015007418-appb-I000022
Figure PCTKR2015007418-appb-I000022
<비교예 14> 유기 발광 소자의 제조Comparative Example 14 Fabrication of Organic Light-Emitting Element
상기 실시예 2에서 상기 화합물 1-1-1 대신 하기 화학식 ET-3을 사용한 것을 제외하고, 실시예 2과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 2 except for using the following Chemical Formula ET-3 instead of the compound 1-1-1 in Example 2.
<비교예 15> 유기 발광 소자의 제조Comparative Example 15 Fabrication of Organic Light-Emitting Element
상기 실시예 3에서 상기 화합물 1-1-1 대신 하기 화학식 ET-3을 사용한 것을 제외하고, 실시예 3과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 3 except for using the following Chemical Formula ET-3 instead of the compound 1-1-1 in Example 3.
<비교예 16> 유기 발광 소자의 제조Comparative Example 16 Fabrication of Organic Light-Emitting Element
상기 실시예 4에서 상기 화합물 1-1-1 대신 하기 화학식 ET-3을 사용한 것을 제외하고, 실시예 4과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 4 except for using the following Chemical Formula ET-3 instead of the compound 1-1-1 in Example 4.
<비교예 17> 유기 발광 소자의 제조Comparative Example 17 Fabrication of Organic Light-Emitting Element
상기 실시예 5에서 상기 화합물 1-1-1 대신 하기 화학식 ET-3을 사용한 것을 제외하고, 실시예 5과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 5 except for using the following Chemical Formula ET-3 instead of the compound 1-1-1 in Example 5.
<비교예 18> 유기 발광 소자의 제조Comparative Example 18 Fabrication of Organic Light-Emitting Element
상기 실시예 6에서 상기 화합물 1-1-1 대신 하기 화학식 ET-3을 사용한 것을 제외하고, 실시예 6과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Example 6 except for using the following Chemical Formula ET-3 instead of the compound 1-1-1 in Example 6.
<비교예 19> 유기 발광 소자의 제조Comparative Example 19 Fabrication of Organic Light-Emitting Element
상기 실시예 1에서 발광층 위에 상기 화합물 2-1의 전자수송층물질과 리튬 퀴놀레이트(LiQ, Lithium Quinolate)를 1: 1의 중량비로 진공증착하여 400Å의 두께로 전자 주입 및 수송층을 형성하였다. In Example 1, the electron transporting layer material of the compound 2-1 and lithium quinolate (LiQ, Lithium Quinolate) were vacuum-deposited at a weight ratio of 1 to 1 to form an electron injection and transport layer at a thickness of 400 Pa.
<비교예 20> 유기 발광 소자의 제조Comparative Example 20 Fabrication of Organic Light-Emitting Element
상기 비교예 19에서 상기 화합물 2-1 대신 화합물 2-3를 사용한 것을 제외하고, 비교예 19와 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 19, except that Compound 2-3 was used instead of Compound 2-1 in Comparative Example 19.
<비교예 21> 유기 발광 소자의 제조Comparative Example 21 Fabrication of Organic Light-Emitting Element
상기 비교예 19에서 상기 화합물 2-1 대신 화합물 2-4를 사용한 것을 제외하고, 비교예 19과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 19, except that Compound 2-4 was used instead of Compound 2-1 in Comparative Example 19.
<비교예 22> 유기 발광 소자의 제조Comparative Example 22 Fabrication of Organic Light-Emitting Element
상기 비교예 19에서 상기 화합물 2-1 대신 화합물 2-7를 사용한 것을 제외하고, 비교예 19과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 19, except that Compound 2-7 was used instead of Compound 2-1 in Comparative Example 19.
<비교예 23> 유기 발광 소자의 제조Comparative Example 23 Fabrication of Organic Light-Emitting Element
상기 비교예 19에서 상기 화합물 2-1 대신 화합물 2-8을 사용한 것을 제외하고, 비교예 19과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 19, except that Compound 2-8 was used instead of Compound 2-1 in Comparative Example 19.
<비교예 24> 유기 발광 소자의 제조Comparative Example 24 Fabrication of Organic Light-Emitting Element
상기 비교예 19에서 상기 화합물 2-1 대신 화합물 2-13을 사용한 것을 제외하고, 비교예 19과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 19, except that Compound 2-13 was used instead of Compound 2-1 in Comparative Example 19.
<비교예 25> 유기 발광 소자의 제조Comparative Example 25 Fabrication of Organic Light-Emitting Element
상기 실시예 1에서 발광층 위에 상기 화합물 1-1-1을 300Å의 두께로 증착하여 전자조절층을 형성하였고 그 위에 상기 화합물 2-1의 전자수송층물질과 리튬 퀴놀레이트(LiQ, Lithium Quinolate)를 1: 1의 중량비로 진공증착하여 100Å의 두께로 전자 주입 및 수송층을 형성하였다.In Example 1, the electron control layer was formed by depositing the compound 1-1-1 to a thickness of 300 전자 on the light emitting layer, and the electron transport layer material of the compound 2-1 and lithium quinolate (LiQ, Lithium Quinolate) 1 Vacuum deposition was carried out at a weight ratio of 1 to form an electron injection and transport layer at a thickness of 100 kPa.
<비교예 26> 유기 발광 소자의 제조Comparative Example 26 Fabrication of Organic Light-Emitting Element
상기 비교예 25에서 상기 화합물 2-1 대신 화합물 2-3을 사용한 것을 제외하고, 비교예 25과 동일한 방법으로 유기 발광 소자를 제작하였다. An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 2-3 was used instead of Compound 2-1 in Comparative Example 25.
<비교예 27> 유기 발광 소자의 제조Comparative Example 27 Fabrication of Organic Light-Emitting Element
상기 비교예 25에서 상기 화합물 2-1 대신 화합물 2-4를 사용한 것을 제외하고, 비교예 25과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 2-4 was used instead of Compound 2-1 in Comparative Example 25.
<비교예 28> 유기 발광 소자의 제조Comparative Example 28 Fabrication of Organic Light-Emitting Element
상기 비교예 25에서 상기 화합물 2-1 대신 화합물 2-7를 사용한 것을 제외하고, 비교예 25과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 2-7 was used instead of Compound 2-1 in Comparative Example 25.
<비교예 29> 유기 발광 소자의 제조Comparative Example 29 Fabrication of Organic Light-Emitting Element
상기 비교예 25에서 상기 화합물 2-1 대신 화합물 2-8을 사용한 것을 제외하고, 비교예 25과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 2-8 was used instead of Compound 2-1 in Comparative Example 25.
<비교예 30> 유기 발광 소자의 제조Comparative Example 30 Fabrication of Organic Light-Emitting Element
상기 비교예 25에서 상기 화합물 2-1 대신 화합물 2-13을 사용한 것을 제외하고, 비교예 25과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 2-13 was used instead of Compound 2-1 in Comparative Example 25.
<비교예 31> 유기 발광 소자의 제조Comparative Example 31 Fabrication of Organic Light-Emitting Element
상기 비교예 25에서 상기 화합물 1-1-1 대신 화합물 1-2-3를 사용한 것을 제외하고, 비교예 25과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 1-2-3 was used instead of Compound 1-1-1 in Comparative Example 25.
<비교예 32> 유기 발광 소자의 제조Comparative Example 32 Fabrication of Organic Light-Emitting Element
상기 비교예 25에서 상기 화합물 1-1-1 대신 화합물 1-2-10을 사용한 것을 제외하고, 비교예 25과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Comparative Example 25.
<비교예 33> 유기 발광 소자의 제조Comparative Example 33 Fabrication of Organic Light-Emitting Element
상기 비교예 25에서 상기 화합물 1-1-1 대신 화합물 1-3-1를 사용한 것을 제외하고, 비교예 25과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Comparative Example 25.
<비교예 34> 유기 발광 소자의 제조Comparative Example 34 Fabrication of Organic Light-Emitting Element
상기 비교예 25에서 상기 화합물 1-1-1 대신 화합물 1-3-2를 사용한 것을 제외하고, 비교예 25과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Comparative Example 25.
<비교예 35> 유기 발광 소자의 제조Comparative Example 35 Fabrication of Organic Light-Emitting Element
상기 비교예 25에서 상기 화합물 1-1-1 대신 화합물 1-4-1를 사용한 것을 제외하고, 비교예 25과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 25, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Comparative Example 25.
<비교예 36> 유기 발광 소자의 제조Comparative Example 36 Fabrication of Organic Light-Emitting Element
상기 비교예 26에서 상기 화합물 1-1-1 대신 화합물 1-2-3를 사용한 것을 제외하고, 비교예 26과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 26, except that Compound 1-2-3 was used instead of Compound 1-1-1 in Comparative Example 26.
<비교예 37> 유기 발광 소자의 제조Comparative Example 37 Fabrication of Organic Light-Emitting Element
상기 비교예 26에서 상기 화합물 1-1-1 대신 화합물 1-2-10을 사용한 것을 제외하고, 비교예 26과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 26, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Comparative Example 26.
<비교예 38> 유기 발광 소자의 제조Comparative Example 38 Fabrication of Organic Light-Emitting Element
상기 비교예 26에서 상기 화합물 1-1-1 대신 화합물 1-3-1를 사용한 것을 제외하고, 비교예 26과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 26, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Comparative Example 26.
<비교예 39> 유기 발광 소자의 제조Comparative Example 39 Fabrication of Organic Light-Emitting Element
상기 비교예 26에서 상기 화합물 1-1-1 대신 화합물 1-3-2를 사용한 것을 제외하고, 비교예 26과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 26, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Comparative Example 26.
<비교예 40> 유기 발광 소자의 제조Comparative Example 40 Fabrication of Organic Light-Emitting Element
상기 비교예 26에서 상기 화합물 1-1-1 대신 화합물 1-4-1를 사용한 것을 제외하고, 비교예 26과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 26, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Comparative Example 26.
<비교예 41> 유기 발광 소자의 제조Comparative Example 41 Fabrication of Organic Light-Emitting Element
상기 비교예 27에서 상기 화합물 1-1-1 대신 화합물 1-2-3를 사용한 것을 제외하고, 비교예 27과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 27, except that Compound 1-2-3 was used instead of Compound 1-1-1 in Comparative Example 27.
<비교예 42> 유기 발광 소자의 제조Comparative Example 42 Fabrication of Organic Light-Emitting Element
상기 비교예 27에서 상기 화합물 1-1-1 대신 화합물 1-2-10을 사용한 것을 제외하고, 비교예 27과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 27, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Comparative Example 27.
<비교예 43> 유기 발광 소자의 제조Comparative Example 43 Fabrication of Organic Light-Emitting Element
상기 비교예 27에서 상기 화합물 1-1-1 대신 화합물 1-3-1를 사용한 것을 제외하고, 비교예 27과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 27, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Comparative Example 27.
<비교예 44> 유기 발광 소자의 제조Comparative Example 44 Fabrication of Organic Light-Emitting Element
상기 비교예 27에서 상기 화합물 1-1-1 대신 화합물 1-3-2를 사용한 것을 제외하고, 비교예 27과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 27, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Comparative Example 27.
<비교예 45> 유기 발광 소자의 제조Comparative Example 45 Fabrication of Organic Light-Emitting Element
상기 비교예 27에서 상기 화합물 1-1-1 대신 화합물 1-4-1를 사용한 것을 제외하고, 비교예 과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light emitting diode was manufactured according to the same method as Comparative Example except for using Compound 1-4-1 instead of Compound 1-1-1 in Comparative Example 27.
<비교예 46> 유기 발광 소자의 제조Comparative Example 46 Fabrication of Organic Light-Emitting Element
상기 비교예 28에서 상기 화합물 1-1-1 대신 화합물 1-2-3를 사용한 것을 제외하고, 비교예28과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 28, except that Compound 1-2-3 was used instead of Compound 1-1-1 in Comparative Example 28.
<비교예 47> 유기 발광 소자의 제조Comparative Example 47 Fabrication of Organic Light-Emitting Element
상기 비교예 28에서 상기 화합물 1-1-1 대신 화합물 1-2-10을 사용한 것을 제외하고, 비교예 28과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 28, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Comparative Example 28.
<비교예 49> 유기 발광 소자의 제조Comparative Example 49 Fabrication of Organic Light-Emitting Element
상기 비교예 28에서 상기 화합물 1-1-1 대신 화합물 1-3-1를 사용한 것을 제외하고, 비교예 28과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 28, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Comparative Example 28.
<비교예 50> 유기 발광 소자의 제조Comparative Example 50 Fabrication of Organic Light-Emitting Element
상기 비교예 28에서 상기 화합물 1-1-1 대신 화합물 1-3-2를 사용한 것을 제외하고, 비교예 28과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 28, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Comparative Example 28.
<비교예 51> 유기 발광 소자의 제조Comparative Example 51 Fabrication of Organic Light-Emitting Element
상기 비교예 28에서 상기 화합물 1-1-1 대신 화합물 1-4-1를 사용한 것을 제외하고, 비교예 28과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 28, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Comparative Example 28.
<비교예 52> 유기 발광 소자의 제조Comparative Example 52 Fabrication of Organic Light-Emitting Element
상기 비교예 29에서 상기 화합물 1-1-1 대신 화합물 1-2-3를 사용한 것을 제외하고, 비교예 29과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 29, except that Compound 1-2-3 was used instead of Compound 1-1-1 in Comparative Example 29.
<비교예 53> 유기 발광 소자의 제조Comparative Example 53 Fabrication of Organic Light-Emitting Element
상기 비교예 29에서 상기 화합물 1-1-1 대신 화합물 1-2-10을 사용한 것을 제외하고, 비교예 29과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 29, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Comparative Example 29.
<비교예 54> 유기 발광 소자의 제조Comparative Example 54 Fabrication of Organic Light-Emitting Element
상기 비교예 29에서 상기 화합물 1-1-1 대신 화합물 1-3-1를 사용한 것을 제외하고, 비교예 29과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 29, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Comparative Example 29.
<비교예 55> 유기 발광 소자의 제조Comparative Example 55 Fabrication of Organic Light-Emitting Element
상기 비교예 29에서 상기 화합물 1-1-1 대신 화합물 1-3-2를 사용한 것을 제외하고, 비교예 29과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 29, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Comparative Example 29.
<비교예 56> 유기 발광 소자의 제조Comparative Example 56 Fabrication of Organic Light-Emitting Element
상기 비교예 29에서 상기 화합물 1-1-1 대신 화합물 1-4-1를 사용한 것을 제외하고, 비교예 29과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 29, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Comparative Example 29.
<비교예 57> 유기 발광 소자의 제조Comparative Example 57 Fabrication of Organic Light-Emitting Element
상기 비교예 30에서 상기 화합물 1-1-1 대신 화합물 1-2-3를 사용한 것을 제외하고, 비교예 30과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 30, except that Compound 1-2-3 was used instead of Compound 1-1-1 in Comparative Example 30.
<비교예 58> 유기 발광 소자의 제조Comparative Example 58 Fabrication of Organic Light-Emitting Element
상기 비교예 30에서 상기 화합물 1-1-1 대신 화합물 1-2-10을 사용한 것을 제외하고, 비교예 30과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 30, except that Compound 1-2-10 was used instead of Compound 1-1-1 in Comparative Example 30.
< 비교예 59> 유기 발광 소자의 제조Comparative Example 59 Fabrication of Organic Light-Emitting Element
상기 비교예 30에서 상기 화합물 1-1-1 대신 화합물 1-3-1를 사용한 것을 제외하고, 비교예 30과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 30, except that Compound 1-3-1 was used instead of Compound 1-1-1 in Comparative Example 30.
< 비교예 60> 유기 발광 소자의 제조Comparative Example 60 Fabrication of Organic Light-Emitting Element
상기 비교예 30에서 상기 화합물 1-1-1 대신 화합물 1-3-2를 사용한 것을 제외하고, 비교예 30과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 30, except that Compound 1-3-2 was used instead of Compound 1-1-1 in Comparative Example 30.
< 비교예 61> 유기 발광 소자의 제조Comparative Example 61 Fabrication of Organic Light-Emitting Element
상기 비교예 30에서 상기 화합물 1-1-1 대신 화합물 1-4-1를 사용한 것을 제외하고, 비교예 30과 동일한 방법으로 유기 발광 소자를 제작하였다.An organic light-emitting device was manufactured in the same manner as in Comparative Example 30, except that Compound 1-4-1 was used instead of Compound 1-1-1 in Comparative Example 30.
전술한 방법으로 제조한 유기 발광 소자를 10 mA/cm2의 전류밀도에서 구동전압과 발광 효율을 측정하였고, 20mA/cm2의 전류밀도에서 초기 휘도 대비 98%가 되는 시간(LT98)을 측정하였다. 그 결과를 하기 표 1에 나타내었다.The driving voltage and the luminous efficiency of the organic light emitting device manufactured by the above-described method were measured at a current density of 10 mA / cm 2 , and the time (LT98) of 98% of the initial luminance at a current density of 20 mA / cm 2 was measured. . The results are shown in Table 1 below.
전압(V)Voltage (V) 전류효율 (cd/A)Current efficiency (cd / A) 색좌표 (x,y)Color coordinates (x, y) Life Time 98 at 20mA/cm2 Life Time 98 at 20mA / cm 2
실시예 1Example 1 4.154.15 5.665.66 (0.137, 0.142)(0.137, 0.142) 5555
실시예 2Example 2 4.084.08 5.885.88 (0.138, 0.142)(0.138, 0.142) 5151
실시예 3Example 3 4.14.1 5.875.87 (0.138, 0.143)(0.138, 0.143) 5050
실시예 4Example 4 4.064.06 5.785.78 (0.139, 0.143)(0.139, 0.143) 5858
실시예 5Example 5 3.893.89 5.885.88 (0.138, 0.142)(0.138, 0.142) 4343
실시예 6Example 6 4.064.06 5.795.79 (0.139, 0.142)(0.139, 0.142) 5757
실시예 7Example 7 4.144.14 5.585.58 (0.138, 0.142)(0.138, 0.142) 5151
실시예 8Example 8 4.114.11 5.595.59 (0.138, 0.143)(0.138, 0.143) 5858
실시예 9Example 9 4.134.13 5.615.61 (0.138, 0.142)(0.138, 0.142) 5252
실시예 10Example 10 4.114.11 5.455.45 (0.138, 0.143)(0.138, 0.143) 5151
실시예 11Example 11 4.104.10 5.775.77 (0.138, 0.142)(0.138, 0.142) 4848
실시예 12Example 12 4.094.09 5.915.91 (0.139, 0.142)(0.139, 0.142) 5151
실시예 13Example 13 4.084.08 5.845.84 (0.139, 0.142)(0.139, 0.142) 4949
실시예 14Example 14 4.094.09 5.835.83 (0.138, 0.142)(0.138, 0.142) 3535
실시예 15Example 15 4.14.1 5.715.71 (0.138, 0.142)(0.138, 0.142) 4242
실시예 16Example 16 4.054.05 5.485.48 (0.138, 0.142)(0.138, 0.142) 7171
실시예 17Example 17 4.14.1 5.875.87 (0.138, 0.142)(0.138, 0.142) 4949
실시예 18Example 18 4.14.1 5.875.87 (0.138, 0.142)(0.138, 0.142) 5555
실시예 19Example 19 4.14.1 5.875.87 (0.138, 0.142)(0.138, 0.142) 6565
실시예 20Example 20 4.14.1 5.875.87 (0.138, 0.142)(0.138, 0.142) 4848
실시예 21Example 21 4.14.1 5.875.87 (0.138, 0.142)(0.138, 0.142) 5555
실시예 22Example 22 4.064.06 5.785.78 (0.138, 0.142)(0.138, 0.142) 5959
실시예 23Example 23 4.094.09 5.785.78 (0.138, 0.142)(0.138, 0.142) 5757
실시예 24Example 24 4.14.1 5.495.49 (0.138, 0.142)(0.138, 0.142) 5252
실시예 25Example 25 4.124.12 5.715.71 (0.138, 0.142)(0.138, 0.142) 4848
실시예 26Example 26 4.154.15 5.755.75 (0.138, 0.142)(0.138, 0.142) 4444
실시예 27Example 27 3.913.91 5.635.63 (0.138, 0.142)(0.138, 0.142) 5252
실시예 28Example 28 4.014.01 5.575.57 (0.138, 0.142)(0.138, 0.142) 5454
실시예 29Example 29 4.044.04 5.625.62 (0.138, 0.142)(0.138, 0.142) 5050
실시예 30Example 30 4.054.05 5.665.66 (0.138, 0.142)(0.138, 0.142) 4949
실시예 31Example 31 3.993.99 5.635.63 (0.138, 0.142)(0.138, 0.142) 4949
실시예 32Example 32 4.094.09 5.915.91 (0.138, 0.142)(0.138, 0.142) 4848
실시예 33Example 33 4.14.1 5.555.55 (0.138, 0.142)(0.138, 0.142) 5252
실시예 34Example 34 4.114.11 5.785.78 (0.138, 0.142)(0.138, 0.142) 5656
실시예 35Example 35 4.074.07 5.695.69 (0.138, 0.142)(0.138, 0.142) 5858
실시예 36Example 36 4.084.08 5.795.79 (0.138, 0.142)(0.138, 0.142) 5858
비교예 1Comparative Example 1 4.454.45 5.155.15 (0.138, 0.142)(0.138, 0.142) 2828
비교예 2Comparative Example 2 4.334.33 5.255.25 (0.138, 0.142)(0.138, 0.142) 1414
비교예 3 Comparative Example 3 4.384.38 5.215.21 (0.138, 0.142)(0.138, 0.142) 1313
비교예 4Comparative Example 4 4.354.35 5.185.18 (0.138, 0.143)(0.138, 0.143) 2525
비교예 5Comparative Example 5 4.294.29 5.285.28 (0.138, 0.141)(0.138, 0.141) 1515
비교예 6Comparative Example 6 4.284.28 5.305.30 (0.137, 0.142)(0.137, 0.142) 2121
비교예 7Comparative Example 7 4.394.39 5.165.16 (0.138, 0.142)(0.138, 0.142) 2828
비교예 8Comparative Example 8 4.294.29 5.055.05 (0.139, 0.142)(0.139, 0.142) 55
비교예 9Comparative Example 9 4.244.24 4.844.84 (0.138, 0.142)(0.138, 0.142) 2626
비교예 10Comparative Example 10 4.194.19 5.065.06 (0.138, 0.142)(0.138, 0.142) 2222
비교예 11Comparative Example 11 4.314.31 5.035.03 (0.138, 0.141)(0.138, 0.141) 2020
비교예 12Comparative Example 12 4.244.24 4.794.79 (0.138, 0.142)(0.138, 0.142) 2020
비교예 13Comparative Example 13 4.34.3 4.894.89 (0.138, 0.141)(0.138, 0.141) 2323
비교예 14Comparative Example 14 4.484.48 5.015.01 (0.137, 0.142)(0.137, 0.142) 1515
비교예 15Comparative Example 15 4.394.39 5.065.06 (0.138, 0.142)(0.138, 0.142) 1919
비교예 16Comparative Example 16 4.194.19 5.155.15 (0.139, 0.142)(0.139, 0.142) 99
비교예 17Comparative Example 17 44 5.055.05 (0.138, 0.142)(0.138, 0.142) 1818
비교예 18Comparative Example 18 4.054.05 5.215.21 (0.139, 0.142)(0.139, 0.142) 1919
비교예 19Comparative Example 19 5.015.01 5.295.29 (0.138, 0.142)(0.138, 0.142) 77
비교예 20Comparative Example 20 5.215.21 5.315.31 (0.138, 0.142)(0.138, 0.142) 1515
비교예 21Comparative Example 21 5.335.33 5.295.29 (0.138, 0.152)(0.138, 0.152) 1212
비교예 22Comparative Example 22 5.115.11 5.315.31 (0.138, 0.146)(0.138, 0.146) 1515
비교예 23Comparative Example 23 5.185.18 5.285.28 (0.138, 0.144)(0.138, 0.144) 1616
비교예 24Comparative Example 24 5.105.10 5.195.19 (0.138, 0.142)(0.138, 0.142) 1111
비교예 25Comparative Example 25 5.015.01 5.195.19 (0.138, 0.142)(0.138, 0.142) 2020
비교예 26Comparative Example 26 4.894.89 5.095.09 (0.138, 0.142)(0.138, 0.142) 2323
비교예 27Comparative Example 27 4.994.99 5.075.07 (0.138, 0.142)(0.138, 0.142) 88
비교예 28Comparative Example 28 5.115.11 5.065.06 (0.138, 0.141)(0.138, 0.141) 1414
비교예 29Comparative Example 29 4.884.88 5.025.02 (0.138, 0.142)(0.138, 0.142) 1515
비교예 30Comparative Example 30 4.654.65 4.904.90 (0.138, 0.142)(0.138, 0.142) 1818
비교예 31Comparative Example 31 4.554.55 5.135.13 (0.138, 0.142)(0.138, 0.142) 1818
비교예 32Comparative Example 32 4.694.69 5.215.21 (0.138, 0.142)(0.138, 0.142) 1414
비교예 33Comparative Example 33 4.704.70 4.904.90 (0.138, 0.142)(0.138, 0.142) 1616
비교예 34Comparative Example 34 4.714.71 4.884.88 (0.138, 0.142)(0.138, 0.142) 1111
비교예 35Comparative Example 35 4.754.75 4.894.89 (0.138, 0.142)(0.138, 0.142) 1010
비교예 36Comparative Example 36 4.704.70 4.744.74 (0.138, 0.142)(0.138, 0.142) 3131
비교예 37Comparative Example 37 4.594.59 5.105.10 (0.138, 0.142)(0.138, 0.142) 2020
비교예 38Comparative Example 38 5.015.01 5.115.11 (0.138, 0.142)(0.138, 0.142) 1818
비교예 39Comparative Example 39 4.964.96 5.095.09 (0.138, 0.142)(0.138, 0.142) 1515
비교예 40Comparative Example 40 5.125.12 4.994.99 (0.138, 0.142)(0.138, 0.142) 1717
비교예 41Comparative Example 41 5.135.13 5.005.00 (0.138, 0.142)(0.138, 0.142) 1010
비교예 42Comparative Example 42 4.954.95 5.025.02 (0.138, 0.142)(0.138, 0.142) 1616
비교예 43Comparative Example 43 5.165.16 4.914.91 (0.138, 0.142)(0.138, 0.142) 1414
비교예 44Comparative Example 44 5.215.21 5.135.13 (0.138, 0.142)(0.138, 0.142) 1818
비교예 45Comparative Example 45 4.984.98 5.115.11 (0.138, 0.142)(0.138, 0.142) 1919
비교예 46Comparative Example 46 5.115.11 4.904.90 (0.138, 0.142)(0.138, 0.142) 2121
비교예 47Comparative Example 47 5.095.09 4.884.88 (0.138, 0.142)(0.138, 0.142) 2525
비교예 48Comparative Example 48 5.085.08 4.904.90 (0.138, 0.142)(0.138, 0.142) 1818
비교예 49Comparative Example 49 5.15.1 4.744.74 (0.138, 0.142)(0.138, 0.142) 1717
비교예 50Comparative Example 50 5.115.11 5.055.05 (0.138, 0.142)(0.138, 0.142) 2525
비교예 51Comparative Example 51 4.784.78 4.894.89 (0.138, 0.142)(0.138, 0.142) 1818
비교예 52Comparative Example 52 5.205.20 5.015.01 (0.138, 0.142)(0.138, 0.142) 2121
비교예 53Comparative Example 53 5.215.21 5.025.02 (0.138, 0.142)(0.138, 0.142) 1818
비교예 54Comparative Example 54 4.754.75 4.954.95 (0.138, 0.142)(0.138, 0.142) 2323
비교예 55Comparative Example 55 4.954.95 5.135.13 (0.138, 0.142)(0.138, 0.142) 2020
비교예 56Comparative Example 56 4.794.79 5.065.06 (0.138, 0.142)(0.138, 0.142) 1414
비교예 57Comparative Example 57 4.924.92 4.714.71 (0.138, 0.142)(0.138, 0.142) 1818
비교예 58Comparative Example 58 5.325.32 5.195.19 (0.138, 0.142)(0.138, 0.142) 1616
비교예 59Comparative Example 59 5.225.22 5.145.14 (0.138, 0.142)(0.138, 0.142) 2929
비교예 60Comparative Example 60 5.125.12 4.844.84 (0.138, 0.142)(0.138, 0.142) 3030
비교예 61Comparative Example 61 5.115.11 4.754.75 (0.138, 0.142)(0.138, 0.142) 3131
상기 표 1의 실시예 1 내지 36과 비교예 1 내지 18의 결과와 같이, 상기 화학식 1로 표시되는 화합물을 전자조절층으로 사용하였을 때 동일하거나 유사한 색좌표 범위 내에서 낮은 구동전압, 높은 전류 효율을 제공하고, 특히 장수명의 유기 발광 소자를 제공함을 확인할 수 있다. As in the results of Examples 1 to 36 and Comparative Examples 1 to 18 of Table 1, when the compound represented by the formula (1) is used as the electronic control layer, the low driving voltage, high current efficiency within the same or similar color coordinate range In particular, it can be seen that an organic light emitting device having a long life is provided.
또한, 비교예 19 내지 24의 결과로 상기 화학식 2를 만족하는 화합물은 화학식 1로 표시되는 전자조절층이 발광층과 전자수송층 사이에 구비되었을 경우에 유기 발광 소자 내에서 전압, 효율 및/또는 수명 면에서 효과를 발현하는 것을 확인할 수 있으며, 비교예 25 내지 비교예 61의 결과는 전자조절층과 전자수송층의 두께와 관련한 유기 발광 소자의 뚜렷한 성능 차이를 나타냄을 확인할 수 있다. In addition, the compounds satisfying the formula (2) as a result of Comparative Examples 19 to 24, when the electron control layer represented by the formula (1) is provided between the light emitting layer and the electron transport layer in terms of voltage, efficiency and / or lifetime in the organic light emitting device It can be seen that the effect is expressed in, and the results of Comparative Examples 25 to 61 can be seen that the distinct performance difference of the organic light emitting device with respect to the thickness of the electron control layer and the electron transport layer.
따라서, 본 명세서의 일 실시상태에 따라 화학식 1로 표시되는 전자조절층과 화학식 2로 표시되는 전자수송층을 동시에 구비하는 유기 발광 소자의 조합시, 높은 효율 및/또는 장수명의 유기 발광 소자를 제공할 수 있다. Accordingly, in combination with an organic light emitting device having an electron control layer represented by Formula 1 and an electron transport layer represented by Formula 2 according to one embodiment of the present specification, an organic light emitting device having high efficiency and / or long life may be provided. Can be.

Claims (13)

  1. 캐소드; Cathode;
    상기 캐소드와 대향하여 구비된 애노드; An anode provided opposite the cathode;
    상기 캐소드와 상기 애노드 사이에 구비된 발광층;A light emitting layer provided between the cathode and the anode;
    상기 캐소드와 상기 발광층 사이에 구비된 전자수송층; 및 An electron transport layer provided between the cathode and the light emitting layer; And
    상기 발광층과 상기 전자수송층 사이에 구비된 전자조절층을 포함하고, It includes an electron control layer provided between the light emitting layer and the electron transport layer,
    상기 전자수송층은 방향족 헤테로고리를 함유하는 유기화합물을 포함하며, The electron transport layer includes an organic compound containing an aromatic hetero ring,
    상기 전자조절층은 하기 화학식 1로 표시되는 헤테로환 화합물을 포함하고, The electron control layer comprises a heterocyclic compound represented by the formula (1),
    상기 전자수송층의 이온화퍼텐셜(Ipm)은 상기 전자조절층의 이온화퍼텐셜(Ipa)보다 큰 것인 유기 발광 소자: An organic light emitting device of which the ionization potential Ip m of the electron transport layer is greater than the ionization potential Ip a of the electron control layer:
    [화학식 1][Formula 1]
    Figure PCTKR2015007418-appb-I000023
    Figure PCTKR2015007418-appb-I000023
    화학식 1에 있어서, In Chemical Formula 1,
    X1은 CR1 또는 N이고, X2는 CR2 또는 N이며,X1 is CR1 or N, X2 is CR2 or N,
    Y1은 CR5 또는 N이고, Y2는 CR6 또는 N이며, Y3는 CR7 또는 N이고, Y4는 CR8 또는 N이며, Y1 is CR5 or N, Y2 is CR6 or N, Y3 is CR7 or N, Y4 is CR8 or N,
    Z1은 CR9 또는 N이고, Z2는 CR10 또는 N이며, Z3는 CR11 또는 N이고, Z4는 CR12 또는 N이며, Z1 is CR9 or N, Z2 is CR10 or N, Z3 is CR11 or N, Z4 is CR12 or N,
    X1, X2, Y1 내지 Y4 및 Z1 내지 Z4는 동시에 N은 아니고, X1, X2, Y1 to Y4 and Z1 to Z4 are not N at the same time,
    R1, R2 및 R5 내지 R12는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기; 또는 치환 또는 비치환된 포스핀옥사이드기이거나, R1, R2 및 R5 내지 R12 중 인접하는 치환기는 서로 결합하여 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리를 형성한다.R1, R2 and R5 to R12 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or a substituted or unsubstituted phosphine oxide group, or adjacent substituents of R1, R2, and R5 to R12 combine with each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heteroring.
  2. 청구항 1에 있어서, The method according to claim 1,
    상기 전자조절층은 상기 발광층과 접하여 구비되는 것인 유기 발광 소자.The electron control layer is an organic light emitting device which is provided in contact with the light emitting layer.
  3. 청구항 1에 있어서, The method according to claim 1,
    상기 전자수송층의 두께는 상기 전자조절층의 두께보다 두꺼운 것인 유기 발광 소자.The thickness of the electron transport layer is an organic light emitting device that is thicker than the thickness of the electron control layer.
  4. 청구항 1에 있어서, The method according to claim 1,
    상기 화학식 1로 표시되는 헤테로환 화합물은 하기 화학식 1A 또는 화학식 1B로 표시되는 것인 유기 발광 소자: The heterocyclic compound represented by Chemical Formula 1 is an organic light emitting device represented by Chemical Formula 1A or Chemical Formula 1B:
    [화학식 1A][Formula 1A]
    Figure PCTKR2015007418-appb-I000024
    Figure PCTKR2015007418-appb-I000024
    [화학식 1B][Formula 1B]
    Figure PCTKR2015007418-appb-I000025
    Figure PCTKR2015007418-appb-I000025
    화학식 1A 및 화학식 1B에 있어서, In Formula 1A and Formula 1B,
    Y1 내지 Y4, Z1 내지 Z4 및 R2는 화학식 1에서 정의한 바와 동일하고, Y1 to Y4, Z1 to Z4 and R2 are the same as defined in Formula 1,
    X3 내지 X6은 서로 동일하거나 상이하고, 각각 독립적으로 CR3 또는 N이며, X3 to X6 are the same as or different from each other, and each independently CR3 or N,
    R3는 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기; 또는 치환 또는 비치환된 포스핀옥사이드기이거나, 인접하는 치환기는 서로 결합하여 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리를 형성한다.Each R 3 is independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or a substituted or unsubstituted phosphine oxide group, or adjacent substituents are bonded to each other to form a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heteroring.
  5. 청구항 1에 있어서, The method according to claim 1,
    상기 화학식 1로 표시되는 헤테로환 화합물은 하기 화학식 1-1 내지 1-4 중 어느 하나로 표시되는 것인 유기 발광 소자: The heterocyclic compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulas 1-1 to 1-4:
    [화학식 1-1][Formula 1-1]
    Figure PCTKR2015007418-appb-I000026
    Figure PCTKR2015007418-appb-I000026
    [화학식 1-2][Formula 1-2]
    Figure PCTKR2015007418-appb-I000027
    Figure PCTKR2015007418-appb-I000027
    [화학식 1-3][Formula 1-3]
    Figure PCTKR2015007418-appb-I000028
    Figure PCTKR2015007418-appb-I000028
    [화학식 1-4][Formula 1-4]
    Figure PCTKR2015007418-appb-I000029
    Figure PCTKR2015007418-appb-I000029
    화학식 1-1 내지 1-4 에 있어서, In Chemical Formulas 1-1 to 1-4,
    a, b 및 c는 각각 1 내지 4의 정수이고, a, b and c are each an integer of 1 to 4,
    d 및 e는 각각 1 내지 6의 정수이며, d and e are each an integer of 1 to 6,
    a, b, c, d 및 e 가 각각 2 이상의 정수인 경우, 각각의 2 이상의 괄호 내의 구조는 서로 동일하거나 상이하고, when a, b, c, d and e are each an integer of 2 or more, the structures in each of the two or more parentheses are the same or different from each other,
    A1 내지 A5 및 R2는 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기; 또는 치환 또는 비치환된 포스핀옥사이드기이다.A1 to A5 and R2 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; A substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; Or a substituted or unsubstituted phosphine oxide group.
  6. 청구항 1에 있어서, The method according to claim 1,
    R1, R2 및 R5 내지 R12 중 적어도 하나는 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 아릴기; 또는 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 포스핀옥사이드기이거나, 인접하는 치환기는 서로 결합하여 시아노기, 아릴기, 헤테로고리기 및 포스핀옥사이드기로 이루어진 군에서 선택되는 1 종 또는 2 종 이상의 치환기로 치환 또는 비치환된 탄화수소고리를 형성하는 것인 유기 발광 소자. At least one of R1, R2 and R5 to R12 is an aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group; Or a phosphine oxide group unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group, or adjacent substituents are bonded to each other to form a cyano group, an aryl An organic light emitting device that forms a substituted or unsubstituted hydrocarbon ring with one or two or more substituents selected from the group consisting of a group, a heterocyclic group and a phosphine oxide group.
  7. 청구항 1에 있어서, The method according to claim 1,
    상기 화학식 1로 표시되는 헤테로환 화합물은 하기 화학식 1-1-1 내지 1-1-7, 1-2-1 내지 1-2-10, 1-3-1 내지 1-3-5 및 1-4-1 내지 1-4-7 중 어느 하나로 표시되는 것인 유기 발광 소자:The heterocyclic compound represented by Formula 1 is represented by the following Formulas 1-1-1 to 1-1-7, 1-2-1 to 1-2-10, 1-3-1 to 1-3-5, and 1- An organic light-emitting device represented by any one of 4-1 to 1-4-7:
    Figure PCTKR2015007418-appb-I000030
    Figure PCTKR2015007418-appb-I000030
    Figure PCTKR2015007418-appb-I000031
    Figure PCTKR2015007418-appb-I000031
    Figure PCTKR2015007418-appb-I000032
    Figure PCTKR2015007418-appb-I000032
    Figure PCTKR2015007418-appb-I000033
    .
    Figure PCTKR2015007418-appb-I000033
    .
  8. 청구항 1에 있어서,The method according to claim 1,
    상기 전자수송층은 하기 화학식 2로 표시되는 방향족 헤테로고리를 함유하는 유기 화합물을 포함하는 것인 유기 발광 소자: The electron transport layer is an organic light emitting device comprising an organic compound containing an aromatic hetero ring represented by the following formula (2):
    [화학식 2][Formula 2]
    Figure PCTKR2015007418-appb-I000034
    Figure PCTKR2015007418-appb-I000034
    화학식 2에 있어서, In Chemical Formula 2,
    X5 및 X6은 서로 동일하거나 상이하고, 각각 독립적으로 N 또는 CH 이고, X5 and X6 are the same as or different from each other, and each independently N or CH,
    Ar1 내지 Ar3는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이다.Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  9. 청구항 8에 있어서, The method according to claim 8,
    Ar1 내지 Ar3는 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 나프틸기; 또는 치환 또는 비치환된 플루오레닐기인 것인 유기 발광 소자. Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted fluorenyl group.
  10. 청구항 8에 있어서, The method according to claim 8,
    Ar1 내지 Ar3 중 적어도 하나는 하기 화학식 3으로 표시되는 것인 유기 발광 소자: At least one of Ar 1 to Ar 3 is an organic light emitting device represented by Formula 3 below:
    [화학식 3][Formula 3]
    Figure PCTKR2015007418-appb-I000035
    Figure PCTKR2015007418-appb-I000035
    화학식 3에 있어서, In Chemical Formula 3,
    o, p 및 q는 0 또는 1이고, o, p and q are 0 or 1,
    1 ≤ o + p + q ≤ 3 이며, 1 ≤ o + p + q ≤ 3,
    r은 1 또는 2이고, r is 1 or 2,
    r이 2 인 경우, 2개의 Ar은 서로 동일하거나 상이하며, when r is 2, two Ar are the same as or different from each other,
    L1 내지 L3는 서로 동일하거나 상이하고, 각각 독립적으로 페닐렌기; 또는 나프탈렌기; 또는 플루오레닐렌기이고, L1 to L3 are the same as or different from each other, and each independently a phenylene group; Or naphthalene group; Or a fluorenylene group,
    Ar은 아릴기 및 헤테로고리기로 이루어진 군에서 선택되는 1 또는 2 이상의 치환기로 치환 또는 비치환된 아릴기; 또는 아릴기 및 헤테로고리기로 이루어진 군에서 선택되는 1 또는 2 이상의 치환기로 치환 또는 비치환된 헤테로고리기이다. Ar is an aryl group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group; Or a heterocyclic group unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group.
  11. 청구항 8에 있어서, The method according to claim 8,
    상기 화학식 2로 표시되는 방향족 헤테로고리를 함유하는 유기 화합물은 하기 화학식 2-1 내지 2-13 중 어느 하나로 표시되는 것인 유기 발광 소자: The organic compound containing the aromatic hetero ring represented by Formula 2 is represented by any one of the following formulas 2-1 to 2-13:
    Figure PCTKR2015007418-appb-I000036
    Figure PCTKR2015007418-appb-I000036
    Figure PCTKR2015007418-appb-I000037
    .
    Figure PCTKR2015007418-appb-I000037
    .
  12. 청구항 1에 있어서, The method according to claim 1,
    상기 유기 발광 소자는 청색 형광 발광을 하는 것인 유기 발광 소자. The organic light emitting diode is an organic light emitting device that emits blue fluorescent light.
  13. 청구항 1에 있어서, The method according to claim 1,
    상기 유기 발광 소자는 정공주입층, 정공수송층, 전자수송층, 전자주입층, 전자저지층 및 정공저지층으로 이루어진 군에서 선택되는 1층 또는 2층 이상을 더 포함하는 것인 유기 발광 소자.The organic light emitting device further comprises one or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an electron blocking layer and a hole blocking layer.
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