Nothing Special   »   [go: up one dir, main page]

CN102575155A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Novel organic electroluminescent compounds and organic electroluminescent device using the same Download PDF

Info

Publication number
CN102575155A
CN102575155A CN2010800349455A CN201080034945A CN102575155A CN 102575155 A CN102575155 A CN 102575155A CN 2010800349455 A CN2010800349455 A CN 2010800349455A CN 201080034945 A CN201080034945 A CN 201080034945A CN 102575155 A CN102575155 A CN 102575155A
Authority
CN
China
Prior art keywords
alkyl
aryl
silyl
heteroaryl
naphthenic base
Prior art date
Legal status (The legal status 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 status listed.)
Pending
Application number
CN2010800349455A
Other languages
Chinese (zh)
Inventor
尹勝洙
金圣珉
金奉玉
权赫柱
阴盛镇
赵英俊
金荣佶
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rohm and Haas Electronic Materials Korea Ltd
Dow Advanced Display Materials Ltd
Original Assignee
Rohm and Haas Electronic Materials Korea Ltd
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.)
Filing date
Publication date
Application filed by Rohm and Haas Electronic Materials Korea Ltd filed Critical Rohm and Haas Electronic Materials Korea Ltd
Publication of CN102575155A publication Critical patent/CN102575155A/en
Pending legal-status Critical Current

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D421/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms
    • C07D421/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D517/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms
    • C07D517/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having selenium, tellurium, or halogen atoms as ring hetero atoms in which the condensed system contains two hetero rings
    • C07D517/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
    • C07F9/65683—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/104—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with other heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Biochemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Electroluminescent Light Sources (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)

Abstract

Provided are novel organic electroluminescent compounds and an organic electroluminescent device including the same. The disclosed organic electroluminescent compounds exhibit high luminescence efficiency in blue color and excellent life property. Thus, they may be used to manufacture OLEDs having very good operation life.

Description

Novel organic electroluminescent compounds and the organic electroluminescence device that uses this compound
Technical field
The present invention relates to novel organic electroluminescent compounds and the organic electroluminescence device that uses this compound.More specifically, the present invention relates to be used as the new organic electroluminescent compounds of blue emitting material and use the organic electroluminescence device of this compound as doping agent.
Background technology
In display device, electroluminescent (EL) device is preferred, because they provide the contrast gradient and the quick speed of response of wide visual angle, excellence as spontaneous display device.Eastman Kodak Co (Eastman Kodak) has at first developed a kind of organic EL device in 1987, this device uses low molecular weight aromatic diamines and aluminum complex as the material [Appl.Phys.Lett.51,913,1987] that forms electroluminescence layer.
In organic EL device, determine that the most important factor of its performance (comprising luminous efficiency and working life) is an electroluminescent material.The ask for something of electroluminescent material comprises the anti-decomposability in high solid-state electroluminescent quantum yield, high electronics and hole migration, the vacuum deposition process, the ability and the stability of formation uniform thin film.
Electroluminescent organic material can rough classification be high molecular weight material and low molecular weight material generally.Low molecular weight material can be divided into metal complexes and metal-free pure electroluminescent organic material, and this depends on molecular structure.Chelant complex for example three (oxine closes) aluminum complex, coumarin derivatives, tetraphenylbutadiene verivate, diphenylethyllene arylene derivatives,
Figure BPA00001499588700011
oxadiazole derivative etc. is known.It is reported, use these materials can obtain the organic electroluminescent from the blue light to ruddiness in the visible region, and can estimate to realize chromatic display.
For blue electroluminescent material, at the DPVBi (compound a) of the emerging product of bright dipping company (Idemitsu Kosan) afterwards, commercialization many materials.Blue material system except the emerging product of bright dipping company; (tertiary butyl) perylene (tetra (t-butyl) perylene) (compound c) is known to the dinaphthyl anthracene (dinaphthylanthracene) (compound b) and four of Kodak, but need more research and develop.Up to now, the known efficient of the toluylene based compound system of the emerging product of bright dipping company with the best.It has power efficiency (power efficiency) and 30000 hours or the longer working life of 6lm/W.But because purity of color is along with the working hour descends, the working life of full-color display only has thousands of hours.Usually, if the electroluminescent wavelength a little to longer wavelength shift, blue coloured electroluminously has superiority aspect luminous efficiency.But it just can not be used for high-quality indicating meter, because can not obtain pure blue.Therefore, be badly in need of improving purity of color, efficient and Research on Thermal Stability and exploitation.
Figure BPA00001499588700021
Summary of the invention
Technical problem
Contriver of the present invention is through making great efforts to have solved the problems referred to above.Therefore, they have invented the new electroluminescent compounds that has excellent luminous efficiency and can realize having the organic electroluminescence device of the working life that significantly improves.
Therefore, the object of the present invention is to provide a kind of luminous efficiency and device working life to have the organic electroluminescent compounds that dopant material is improved and has the excellent skeleton (backbone) that meets suitable chromaticity coordinates relatively now, to address the above problem.Another object of the present invention provides uses the organic electroluminescence device of organic electroluminescent compounds as electroluminescent material.
Technical scheme
One common aspect, the invention provides a kind of organic electroluminescent compounds of representing by Chemical formula 1 and the organic electronic devices that comprises this compound.Because organic electroluminescent compounds of the present invention has good illumination efficiency and excellent life properties, it can be used for making the OLED equipment with very good working life.
Figure BPA00001499588700031
Wherein
A representes hydrogen or
Figure BPA00001499588700032
Ar 1And Ar 2Represent chemical bond, (C6-C60) arylidene separately or comprise heteroatomic (C2-C60) inferior heteroaryl of one or more N of being selected from, O and S, the carbon atom of wherein said inferior heteroaryl also can be replaced by Se;
Z 1To Z 5At least one and Z 11To Z 15At least one be nitrogen-atoms, remaining is carbon atom, wherein nitrogen-atoms does not have substituting group;
R 1To R 5And R 11To R 15Represent hydrogen, deuterium, (C1-C60) alkyl, (C3-C60) naphthenic base, (C6-C60) aryl, (C2-C60) heteroaryl, (C1-C60) alkoxyl group, (C6-C60) aryloxy, list-or two (C1-C60) alkylamino, list-or two (C6-C60) arylamino, (C6-C60) aryl (C1-C60) alkylamino, three (C1-C60) alkyl silyl, two (C1-C60) alkyl (C6-C60) aryl silyl or three (C6-C60) aryl silyl, wherein R independently 1To R 5Or R 11To R 15Each can be through being with or without condensed ring (C3-C60) alkylidene group or (C3-C60) alkenylene be connected to adjacent substituting group and form condensed ring, the carbon atom of said alkylidene group also can be by O, S or NR 21Replace, and the CH of alkenylene also can be replaced by N;
R 21Expression hydrogen; Deuterium; (C1-C60) alkyl; Halo (C1-C60) alkyl; (C1-C60) alkoxyl group; Morpholino (morpholino); Thiomorpholine generation (thiomorpholino); Piperidyl (piperidino); Comprise one or more N of being selected from; The heteroatomic 5-of O and S or 6-unit Heterocyclylalkyl; (C3-C60) naphthenic base; Adamantyl; Halogen; Cyanic acid; (C6-C60) aryl; (C2-C60) heteroaryl; Three (C1-C60) alkyl silyl; Two (C1-C60) alkyl (C6-C60) aryl silyl or three (C6-C60) aryl silyl;
X and Y represent independently chemical bond ,-(CR 31R 32) n-,-N (R 33)-,-Si (R 34) (R 35)-,-O-,-S-,-Se-,-P (R 36)-or-(R 37) C=C (R 38)-, wherein n is the integer of 1-4;
R 31To R 38Represent hydrogen, deuterium, (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxyl group, morpholino, thiomorpholine generation, piperidyl, the heteroatomic 5-that comprises one or more N of being selected from, O and S or 6-unit Heterocyclylalkyl, (C3-C60) naphthenic base, adamantyl, halogen, cyanic acid, (C6-C60) aryl, (C2-C60) heteroaryl, three (C1-C60) alkyl silyl, two (C1-C60) alkyl (C6-C60) aryl silyl or three (C6-C60) aryl silyl, perhaps R independently 31And R 32, R 34And R 35Perhaps R 37And R 38Can be independently through being with or without condensed ring (C3-C12) alkylidene group or (C3-C12) alkenylene be connected to form volution or condensed ring; And
Ar 1And Ar 2Arylidene or heteroarylidene, and R 1To R 5, R 11To R 15, R 21And R 31To R 38Alkyl; Naphthenic base; Aryl; Heteroaryl; Alkoxyl group; Aryloxy; Alkylamino; Arylamino; Aryl alkyl amino; Trialkylsilkl; Di alkylaryl silyl or diarye silyl also can replace by being selected from following substituent one or more substituting groups: deuterium; (C1-C60) alkyl; Halo (C1-C60) alkyl; (C1-C60) alkoxyl group; Piperidyl; Morpholino; Thiomorpholine generation; Comprise one or more N of being selected from; The heteroatomic 5-of O and S or 6-unit Heterocyclylalkyl; (C3-C60) naphthenic base; Halogen; Cyanic acid; (C6-C60) aryl; (C2-C60) heteroaryl; (C6-C60) aryl (C1-C60) alkyl; (C1-C60) alkyl (C6-C60) aryl; Three (C1-C60) alkyl silyl; Two (C1-C60) alkyl (C6-C60) aryl silyl and three (C6-C60) aryl silyl.
In the present invention, the substituting group that comprises " (C1-C60) alkyl " can have 1-60 carbon atom, preferred 1-20 carbon atom, more preferably 1-10 carbon atom.The substituting group that comprises " (C6-C60) aryl " can have 6-60 carbon atom, preferred 6-20 carbon atom, more preferably 6-12 carbon atom.The substituting group that comprises " (C3-C60) heteroaryl " can have 3-60 carbon atom, preferred 4-20 carbon atom, more preferably 4-12 carbon atom.The substituting group that comprises " (C3-C60) naphthenic base " can have 3-60 carbon atom, preferred 3-20 carbon atom, more preferably 3-7 carbon atom.The substituting group that comprises " (C2-C60) alkenyl or alkynyl " can have 2-60 carbon atom, preferred 2-20 carbon atom, more preferably 2-10 carbon atom.
In the present invention, " alkyl " comprises the saturated primary alkyl of straight or branched, and it only is made up of carbon and Wasserstoffatoms, or its combination, and " alkoxyl group " expression-O-alkyl, and wherein alkyl is same as described above.
In the present invention, " aryl " represented through remove the organic group that a Wasserstoffatoms obtains from aromatic hydrocarbon, can be comprised monocycle or the condensed ring of 4-to 7-unit, preferred 5-or 6-unit.In addition, said aryl comprises the two or more aryl that connect through chemical bond.Object lesson comprises phenyl, naphthyl, xenyl (biphenyl), anthryl, indenyl, fluorenyl, phenanthryl (phenanthryl), benzo [9; 10] phenanthryl (triphenylenyl), pyrenyl 、 perylene base (perylenyl),
Figure BPA00001499588700041
base (chrysenyl), naphthacenyl (naphthacenyl), fluoranthene base (fluoranthenyl) etc., but be not limited thereto.
In the present invention, to comprise the heteroatoms that 1-4 is selected from N, O and S be the aryl of carbon as aromatic ring frame atom, other aromatic ring frame atoms in " heteroaryl " expression.It can be 5-or 6-unit's bicyclic heteroaryl or the polyheteroaromatic that obtains with the phenyl ring condensation, but and fractional saturation.In addition, said heteroaryl comprises the two or more heteroaryls that connect through chemical bond.Said heteroaryl comprises divalent aryl, wherein the heteroatoms in the ring can oxidized or quaternized formation for example N-oxide compound or quaternary ammonium salt.Concrete example comprises for example furyl of bicyclic heteroaryl; Thienyl; Pyrryl; Imidazolyl; Pyrazolyl; Thiazolyl; Thiadiazolyl group; Isothiazolyl; Different
Figure BPA00001499588700051
azoles base; azoles base;
Figure BPA00001499588700053
di azoly; Triazinyl; The tetrazine base; Triazolyl; Tetrazyl; Furazan base (furazanyl); Pyridyl; Pyrazinyl; Pyrimidyl; Pyridazinyl etc.; Polyheteroaromatic is benzo furazan base (benzofuranyl) for example; Benzothienyl; Isobenzofuran-base; Benzimidazolyl-; Benzothiazolyl; The benzisothiazole base; Benzisoxa azoles base; Benzo
Figure BPA00001499588700055
azoles base; Pseudoindoyl; Indyl; Indazolyl; The diazosulfide base; Quinolyl; Isoquinolyl; Cinnolines base (cinnolinyl); Quinazolyl; Quinoxalinyl (quinoxalinyl); Carbazyl; Phenanthridinyl (phenanthridinyl); Benzo dioxolyl (benzodioxolyl) etc.; And N-oxide compound (for example pyridyl N-oxide compound, quinolyl N-oxide compound etc.); And quaternary ammonium salt etc., but be not limited to this.
In the present invention, " volution " representes that wherein two rings are only shared atom (sp 3Carbon) alkyl.Two shared atoms of ring are called spiro atom (" spiral shell " is the Greek of expression spiral), and can be carbon or silicon.
Organic electroluminescent compounds of the present invention comprises the compound of chemical formula (2) or (3) expression:
Figure BPA00001499588700056
Wherein X, Y, Ar 1, Ar 2, Z 1To Z 5, Z 11To Z 15, R 1To R 15And R 11To R 15Identical with shown in the Chemical formula 1.
R 1To R 5And R 11To R 15Can represent hydrogen, deuterium, CD independently 3Methyl; Ethyl; N-propyl; Sec.-propyl; Normal-butyl; Isobutyl-; The tertiary butyl; N-pentyl; Isopentyl; N-hexyl; N-heptyl; N-octyl; The 2-ethylhexyl; N-nonyl; Decyl; Dodecyl; Hexadecyl; Benzyl; Trifluoromethyl; The perfluor ethyl; Trifluoroethyl; Perfluoro propyl; Perfluoro butyl; Methoxyl group; Oxyethyl group; Positive propoxy; Isopropoxy; N-butoxy; Isobutoxy; Tert.-butoxy; N-pentyloxy; Isopentyloxy; Positive hexyloxy; Positive heptan the oxygen base; Cyclopropyl; Cyclobutyl; Cyclopentyl; Cyclohexyl; Suberyl; The ring octyl group; The ring nonyl; The ring decyl; C 6D 5, phenyl, tolyl, butyl phenyl, naphthyl, xenyl, fluorenyl, phenanthryl, anthryl, fluoranthene base (fluoranthenyl), benzo [9,10] phenanthryl (triphenylenyl), pyrenyl,
Figure BPA00001499588700061
Base (chrysenyl), naphthacenyl (naphthacenyl) 、 perylene base (perylenyl), pyridyl, pyrryl, furyl, thienyl, imidazolyl, benzimidazolyl-, piperazinyl, pyrimidyl, pyridazinyl, quinolyl, triazinyl, benzofuryl, benzothienyl, pyrazolyl, indyl, carbazyl, thiazolyl,
Figure BPA00001499588700062
Azoles base, benzothiazolyl, benzo
Figure BPA00001499588700063
Azoles base, phenanthroline base (phenanthrolinyl), phenoxy, dimethylamino, monomethyl amino, benzylamino, trimethyl silyl, triethylsilyl, tripropyl silyl, three (tertiary butyl) silyl, t-butyldimethylsilyl, 3,5-dimethylphenyl silyl or triphenyl silyl, perhaps R 1To R 5Or R 11To R 15Each can be through being with or without the C3-C60 of condensed ring) alkylidene group or (C3-C60) alkenylene be connected to adjacent substituting group, form condensed ring, and the CH of said alkenylene can be replaced also by N.
Figure BPA00001499588700064
can be independently selected from following structure, but is not limited thereto:
Figure BPA00001499588700066
can be selected from following structure, but is not limited thereto:
Figure BPA00001499588700071
Wherein
R 31To R 38Represent hydrogen, deuterium, (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxyl group, morpholino, thiomorpholine generation, piperidyl, the heteroatomic 5-that comprises one or more N of being selected from, O and S or 6-unit Heterocyclylalkyl, (C3-C60) naphthenic base, adamantyl, halogen, cyanic acid, (C6-C60) aryl, (C2-C60) heteroaryl, three (C1-C60) alkyl silyl, two (C1-C60) alkyl (C6-C60) aryl silyl or three (C6-C60) aryl silyl independently; And
R 21To R 28Alkyl; Naphthenic base; Aryl; Heteroaryl; Alkoxyl group; Trialkylsilkl; Di alkylaryl silyl or diarye silyl also can replace by being selected from following substituent one or more substituting groups: deuterium; (C1-C60) alkyl; Halo (C1-C60) alkyl; (C1-C60) alkoxyl group; Piperidyl; Morpholino; Thiomorpholine generation; Comprise one or more N of being selected from; The heteroatomic 5-of O and S or 6-unit Heterocyclylalkyl; (C3-C60) naphthenic base; Halogen; Cyanic acid; (C6-C60) aryl; (C2-C60) heteroaryl; (C6-C60) aryl (C1-C60) alkyl; (C1-C60) alkyl (C6-C60) aryl; Three (C1-C60) alkyl silyl; Two (C1-C60) alkyl (C6-C60) aryl silyl and three (C6-C60) aryl silyl.
Ar 1And Ar 2Can represent chemical bond independently or be selected from the arylidene or the inferior heteroaryl of following structure, but be not limited to:
Figure BPA00001499588700081
Wherein
R 41The expression deuterium; (C1-C60) alkyl; Halo (C1-C60) alkyl; (C1-C60) alkoxyl group; Piperidyl; Morpholino; Thiomorpholine generation; Comprise one or more N of being selected from; The heteroatomic 5-of O and S or 6-unit Heterocyclylalkyl; (C3-C60) naphthenic base; Halogen; Cyanic acid; (C6-C60) aryl; (C2-C60) heteroaryl; (C6-C60) aryl (C1-C60) alkyl; (C1-C60) alkyl (C6-C60) aryl; Three (C1-C60) alkyl silyl; Two (C1-C60) alkyl (C6-C60) aryl silyl or three (C6-C60) aryl silyl; And
M is the integer of 0-4;
More specifically, Ar 1And Ar 2Can represent chemical bond independently or be selected from the arylidene or the inferior heteroaryl of following structure, but be not limited to:
Figure BPA00001499588700091
Organic electroluminescent compounds of the present invention can be following compound, but is not limited thereto:
Figure BPA00001499588700101
Figure BPA00001499588700111
Figure BPA00001499588700121
Organic electroluminescent compounds of the present invention can prepare according to following proposal 1:
Scheme 1
Figure BPA00001499588700131
Wherein X, Y, Ar 1, Ar 2, Z 1To Z 5, Z 11To Z 15, R 1To R 15And R 11To R 15Identical with shown in the Chemical formula 1.
In aspect another is common, the invention provides a kind of organic electroluminescent device, said equipment comprises: first electrode; Second electrode; And inserting one or more layers organic layer between said first electrode and second electrode, said organic layer comprises the organic electroluminescent compounds that one or more Chemical formula 1s are represented.
Said organic layer can comprise one or more organic electroluminescent compounds that Chemical formula 1 representes as the electroluminescent doping agent, and can comprise one or more matrix (host).Be used for the not special restriction of matrix of organic electroluminescent device of the present invention, but can be selected from the compound of chemical formula 4 or 5 expressions.The example of the concrete structure of the matrix compounds of chemical formula (4) or (5) expression arrives < 210>referring to < 162>among the korean patent application 10-2008-0060393, but is not limited thereto.
(Ar 11) c-L 1-(Ar 12) d(4)
(Ar 13) e-L 2-(Ar 14) f(5)
Wherein
L 1Expression (C6-C60) arylidene or (C4-C60) inferior heteroaryl;
L 2The expression anthrylene;
Ar 11To Ar 14Represent hydrogen, deuterium, (C1-C60) alkyl, (C1-C60) alkoxyl group, halogen, (C4-C60) heteroaryl, (C5-C60) naphthenic base or (C6-C60) aryl separately, said Ar 11To Ar 14Naphthenic base; Aryl or heteroaryl also can replace by being selected from following substituent one or more substituting groups: (said substituting group is selected from deuterium by one or more substituting groups; (C1-C60) alkyl; Halo (C1-C60) alkyl; (C1-C60) alkoxyl group; (C3-C60) naphthenic base; Halogen; Cyanic acid; Three (C1-C60) alkyl silyl; Two (C1-C60) alkyl (C6-C60) aryl silyl and three (C6-C60) aryl silyl) replace or unsubstituted (C6-C60) aryl or (C4-C60) heteroaryl; Deuterium; (C1-C60) alkyl; Halo (C1-C60) alkyl; (C1-C60) alkoxyl group; (C3-C60) naphthenic base; Halogen; Cyanic acid; Three (C1-C60) alkyl silyl; Two (C1-C60) alkyl (C6-C60) aryl silyl and three (C6-C60) aryl silyl; And
C, d, e and f are the integer of 0-4 independently.
Said electroluminescence layer is that electroluminescent layer takes place, and can be formed by individual layer or two-layer or multilayer.When using matrix of the present invention-doping agent system, electroluminescent matrix of the present invention can obviously improve electroluminescent efficiency.Said doping content can be 0.5-10 weight %.When comparing with existing other substrate material, electroluminescent matrix of the present invention can provide excellent hole and electronic conductivity, and very excellent stability and the electroluminescent efficiency and the working life that obviously improve.Therefore, when the compound of selecting chemical formula (4) or (5) expression as electroluminescent matrix, can obviously compensate the electric defective of the organic electroluminescent compounds of chemical formula of the present invention (1) expression.
In organic electronic devices of the present invention, except the organic electroluminescent compounds that Chemical formula 1 is represented, said organic layer can comprise simultaneously that also one or more are selected from the compound of arylamine and styryl aromatic amine compound.The example of said aromatic amine compound or styryl aromatic amine compound arrives < 224>referring to < 212>among the korean patent application 10-2008-0060393, but is not limited thereto.
In addition; In organic electronic devices of the present invention; Except the organic electroluminescent compounds that Chemical formula 1 is represented, said organic layer can comprise that also one or more are selected from the metal of the organo-metallic of the periodic table of elements the 1st family, the 2nd family, period 4 and period 5 transition metal, lanthanide series metal and d-transition element.Said organic layer can comprise electroluminescence layer and charge generation layer.
Can realize having the organic electroluminescent device of the dot structure of independent light-emitting mode; Wherein pattern parallelization (pattern) comprises the organic electroluminescence device of the organic electroluminescent compounds of chemical formula of the present invention (1) as one or more sub-pixels simultaneously, and said sub-pixel comprises one or more metals that is selected from Ir, Pt, Pd, Rh, Re, Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag.
In addition, except said organic electroluminescent compounds, said organic layer also can comprise the organic electro luminescent layer of one or more emission blue light, ruddiness or green glows simultaneously, to realize the organic electroluminescence device of emission white light.The example of the compound of blue light-emitting, green glow or ruddiness can be the compound among korean patent application 10-2008-0123276,10-2008-0107606 or the 10-2008-0118428, but is not limited thereto.
In organic electroluminescence device of the present invention, the layer (below be called " upper layer ") that is selected from chalcogenide layer, metal halide and metal oxide layer can be arranged on the internal surface of one or two electrode in the electrode pair.More particularly, the chalkogenide of silicon or aluminium (comprising oxide compound) layer can place on the anode surface of electroluminescent medium layer, and metal halide or metal oxide layer can place on the cathode surface of said electroluminescent medium layer.Thereby obtain job stability.For example, chalkogenide can be SiO x(1≤x≤2), AlO x(1≤x≤1.5), SiON, SiAlON etc.For example, metal halide can be LiF, MgF 2, CaF 2, rare earth metal fluorochemical etc.For example, MOX can be Cs 2O, Li 2O, MgO, SrO, BaO, CaO etc.
In organic electroluminescence device of the present invention, the mixing zone of electric transmission compound and reductibility doping agent also preferably is set, perhaps the mixing zone of hole transport compound and oxidisability doping agent at least one surface of prepared electrode pair.Therefore, because the electric transmission compound is reduced into negatively charged ion, thereby promotes electronics to inject and be transferred to electroluminescent medium from the mixing zone.In addition, because the hole transport compound oxidation forms positively charged ion, thereby promote the hole to inject and be transferred to electroluminescent medium from the mixing zone.Preferred oxidisability doping agent comprises various Lewis acids and acceptor compound.The preferred embodiment of reductibility doping agent comprises basic metal, alkali metal cpd, earth alkali metal, rare earth metal and composition thereof.
Beneficial effect
Because organic electroluminescent compounds of the present invention has good blue-light-emitting efficient and excellent life properties, it can be used for making the OLED equipment with very good working life.
The invention embodiment
The electroluminescent character that the present invention has further described organic electroluminescent compounds of the present invention, prepared the technology of this compound and use the equipment of this compound.But these embodiment only are for the purpose of setting forth, rather than in order to limit scope of the present invention.
[preparation example 1] preparation compound 2
Figure BPA00001499588700161
Preparation compound (A)
With 9,9-diethylammonium-9H-fluorenes (7g, 32.11mmol) and Paraformaldehyde 96 (paraformaldehyde) (9.4g 32.11mmol) joins in the 100mL round-bottomed flask.After the dried in vacuum, nitrogen injection.After in flask, adding 30%HBr (50mL), said mixture heating up to 60 ℃, and stirred 24 hours.After reaction is accomplished, use CHCl 3Extract.Use NaHCO 3After washing 3 times, product is with brine wash 3 times.Obtain compd A (13g, 31.8mmol, 99%).
The preparation of compd B
(5.00g 12.24mmol) joins in the 50mL round-bottomed flask with compd A.After the dried in vacuum, nitrogen injection.Add triethyl-phosphite (8.1mL, 48.96mmol) after, under refluxad stirred the mixture 6 hours in 185 ℃.After reaction is accomplished, use vacuum distilling apparatus to remove remaining triethyl-phosphite.Behind distilled water wash, use ethyl acetate extraction.Use MgSO 4Dry organic layer uses rotatory evaporator to remove and desolvates.Use ETHYLE ACETATE to obtain compd B (4.9g, 9,37mmol, 76%) through column chromatography purification as eluent.
The preparation of Compound C
With the 2-bromoquinoline (5g, 24mmol), 4-formyl radical phenyl-boron dihydroxide (3.59g, 24mmol) and tetrakis triphenylphosphine palladium (1.11g 0.96mmol) joins in the 1000mL round-bottomed flask, and dissolves with toluene (168mL).(84mL, 168.2mmol) with behind the ethanol (84mL), mixture is under refluxad in 120 ℃ of stirrings 2 hours in flask, to add the 2.0M aqueous sodium carbonate.After reaction is accomplished, use ETHYLE ACETATE to extract.Purified obtains Compound C (5g, 21.4mmol, 89%).
The preparation of compound (2)
Compd B (5g, 9.56mmol) and Compound C (4.46g 19.13mmol) joins in the 250mL round-bottomed flask.After the dried in vacuum, nitrogen injection.After adding THF (50mL), (19.13mmol), and mixture stirred 10 minutes for 1.0M in THF, 19mL slowly to add potassium tert.-butoxide in 0 ℃.After being heated to room temperature, mixture restir 1 hour.Reaction adds excessive zero(ppm) water after accomplishing, and filters the deposition that therefore forms.Filtering solid cleans with ethanol, and purifying obtains compound 2 (3.25g, 4.78mmol, 50%).
1H?NMR(CDCl3，200MHz)δ＝0.9(6H，m)，1.91(4H，m)，6.95(4H，m)，7.35(2H，m)，7.54-7.6(8H，m)，7.71(2H，m)，7.78(2H，m)，7.87(2H，m)，7.98(2H，m)，8.06-8.1(4H，m)，8.3(4H，m)。
[preparation example 2] preparation compound 63
Figure BPA00001499588700171
The preparation of compound (63)
Compd B (5g, 9.56mmol) and quinoline-2-aldehyde (3g 19.13mmol) joins in the 250mL round-bottomed flask.After the dried in vacuum, nitrogen injection.After adding THF (50mL), (19.13mmol), and mixture stirred 10 minutes for 1.0M in THF, 19mL slowly to add potassium tert.-butoxide in 0 ℃.After being heated to room temperature, mixture restir 1 hour.Reaction adds excessive zero(ppm) water after accomplishing, and filters the deposition that therefore forms.Filtering solid cleans with ethanol, and purifying obtains compound 63 (4.5g, 8.51mmol, 90%).
1H?NMR(CDCl3，200MHz)δ＝0.9(6H，m)，1.91(4H，m)，7.2(2H，m)，7.37-7.42(4H，m)，7.56-7.6(6H，m)，7.78-7.82(4H，m)，7.98(2H，m)，8.06(2H，m)，8.24(2H，m)。
[preparation example 3] preparation compound 64
Figure BPA00001499588700181
The preparation compound F 17-hydroxy-corticosterone
(730mg 6.3mmol) joins in the 250mL flask, and dissolves with THF (40mL) with butylmagnesium chloride.Be cooled to-10 ℃ and add n-Butyl Lithium (5.1mL) after, mixture stirred 1 hour, simultaneously temperature was remained on-10 ℃.(3.5g 17mmol) joins in-30 ℃ the flask will to be dissolved in 3-bromoquinoline among the THF (20mL).After temperature being risen to-10 ℃, mixture stirred 2 hours.To be dissolved in 2 among the THF (30mL), (4g is 17mmol) with Pd (dba) for the 5-dibromo pyridine 2(480mg, 830 μ mol) and dppf (470mg, 830 μ mol) add together.After-10 ℃ of stirrings 1 hour and being heated to room temperature, mixture stirred 18 hours.Then, add saturated NH 4The Cl aqueous solution is with termination reaction.Behind ethyl acetate extraction, use MgSO 4Dry organic layer uses rotatory evaporator to remove and desolvates.Purified obtains compound F 17-hydroxy-corticosterone (2.5g, 8.76mmol, 53%).
Preparation compound G
(2.5g 10.7mmol) joins in the 100mL round-bottomed flask with compound F 17-hydroxy-corticosterone.After the dried in vacuum, inject argon gas.After adding THF (25mL) and being cooled to-78 ℃, (5mL, 12.84mmol), and mixture stirred 1 hour, kept low temperature simultaneously slowly to add n-Butyl Lithium.In-78 ℃ add DMF (1mL, 12.84mmol) after, mixture stirred 1 hour.After reaction is accomplished, add 1M HCl in 0 ℃.With distilled water wash and with behind the ethyl acetate extraction, use MgSO 4Dry organic layer uses rotatory evaporator to remove and desolvates.Purified obtains compound G (1.68g, 7.17mmol, 82%).
The preparation of compound (64)
Compound G (1.68g, 7.17mmol) and compd B (1.7g 3.25mmol) joins in the 250mL round-bottomed flask.After the dried in vacuum, nitrogen injection.Add THF (20mL), (3.25mmol), mixture stirred 10 minutes for 1.0M in THF, 3.25mL slowly to add potassium tert.-butoxide in 0 ℃.After being heated to room temperature, mixture restir 1 hour.After reaction is accomplished, use ETHYLE ACETATE to extract.Use MgSO 4Dry organic layer uses rotatory evaporator to remove and desolvates.Purified obtains compound 64 (1.55g, 2.26mmol, 70%).
1H?NMR(CDCl 3，200MHz)δ＝0.9(6H，m)，1.91(4H，m)，6.95(4H，m)，7.42(2H，m)，7.59-7.6(4H，m)，7.68(2H，m)，7.78-7.82(4H，m)，7.98(2H，m)，8.06(2H，m)，8.29-8.36(6H，m)，8.93(2H，m)。
[preparation example 4] preparation compound 65
Figure BPA00001499588700191
The preparation of compound (H)
With 2-bromo-9, (10g 33.19mmol) joins in the 500mL round-bottomed flask 9-diethylammonium-9H-fluorenes.After the dried in vacuum, inject argon gas.After adding THF (250mL) and being cooled to-78 ℃, slowly add n-Butyl Lithium (19.9mL, 49.79mmol).After keeping low temperature and stirring 1 hour simultaneously, (3.8mL, 49.79mmol), and said mixture stirred 1 hour to add DMF in-78 ℃.After reaction is accomplished, add 1M HCl in 0 ℃.With distilled water wash and with behind the ethyl acetate extraction, use MgSO 4Dry organic layer uses rotatory evaporator to remove and desolvates.Purified obtains compound H (6g, 72%).
Preparation compound (J)
(6.7g 28.72mmol) joins in the 100mL round-bottomed flask with compound I.After adding THF (250mL) and being cooled to 0 ℃, slowly add NaBH 4(1.4g, 37.34mmol) and MeOH (6mL).Then, mixture was in stirring at room 2 hours.When reaction is accomplished,, use MgSO with distilled water wash and with behind the ethyl acetate extraction 4Dry organic layer uses rotatory evaporator to remove and desolvates.Purified obtains compound J (6g, 89%).
The preparation compound K
(6g 25.50mmol) joins in the 50mL round-bottomed flask with compound J.Add P (OEt) 3(8.5mL 51.0mmol) and after being cooled to 0 ℃, slowly adds I 2(6.4g 25.50mmol), and stirred the mixture 10 minutes in 0 ℃.Then, spend the night in 120 ℃ of backflows.Reaction is removed P (OEt) through distillation after accomplishing 3With distilled water wash and with behind the ethyl acetate extraction, use MgSO 4Dry organic layer uses rotatory evaporator to remove and desolvates.Purified obtains compound K (5.1g, 59%).
The preparation of compound (65)
Compound H (3g, 11.98mmol) and compound K (4.8g 14.38mmol) joins in the 250mL round-bottomed flask.After the dried in vacuum, inject argon gas.After adding THF (100mL) and being cooled to 0 ℃, (14.3mL, 14.38mmol), and mixture was in stirring at room 3 hours slowly to add KO (t-Bu).When reaction is accomplished,, use MgSO with distilled water wash and with behind the ethyl acetate extraction 4Dry organic layer uses rotatory evaporator to remove and desolvates.Purified obtains compound 65 (3.3g, 61%).
1H?NMR(CDCl 3，200MHz)δ＝0.9(6H，m)，1.91(4H，m)，6.95(2H，m)，7.28(1H，m)，7.35-7.38(2H，m)，7.54-7.6(5H，m)，7.71(1H，m)，7.78(1H，m)，7.87(2H，m)，7.98(1H，m)，8.06-8.1(2H，m)，8.3(2H，m)。
Method according to the routine 1-4 of preparation prepares compound 1-62.The prepared organic electroluminescent compounds 1H NMR and MS/FAB data rows are in table 1.
Table 1
Figure BPA00001499588700211
Figure BPA00001499588700221
Figure BPA00001499588700251
Figure BPA00001499588700261
[embodiment 1-7] uses electroluminescent compounds of the present invention to prepare the OLED device
Use electroluminescent material of the present invention to make the OLED device.At first; (15 Ω/) (available from SCP company (Samsung-Corning)) carry out ultrasonic cleaning with trieline, acetone, ethanol and zero(ppm) water to the transparency electrode ito thin film that is used for OLED successively that will be processed by glass, and before using, are stored in the Virahol.Then, the ITO substrate is contained in the substrate folder (folder) of vacuum vapor deposition equipment, 4; 4 ', 4 " three (N, N-(2-naphthyl)-phenyl amino) triphenylamine (2-TNATA) places the cell (cell) of vacuum vapor deposition equipment; then, exhaust makes indoor vacuum tightness be up to 10 -6Holder.Then, through applying electric current to said cell, on the ITO base material, form the thick hole injection layer of 60nm with evaporation 2-TNATA.
Then, in another cell of vacuum sediment equipment, add N, N '-two (Alpha-Naphthyl)-N, N '-phenylbenzene-4,4 '-diamines (NPB) is through apply electric current evaporation NPB to said cell, with the thick hole transmission layer of deposition 20nm on said hole injection layer.
After forming hole injection layer and hole transport layer, form electroluminescence layer in the above, specific as follows.DNA (embodiment 1-4) or compound H-33 place the cell of vacuum sediment equipment interior as matrix, and organic electroluminescent compounds of the present invention places in another cell as doping agent.Two kinds of materials with 100: 1 speed vapour deposition with the thick electroluminescence layer of deposition 30nm on said hole transmission layer.
Afterwards, three (oxines) that vapour deposition 20nm is thick close-aluminium (III) is (Alq) as electron transfer layer, and the thick quinoline of vapour deposition 1-2nm closes lithium (Liq) as electron injecting layer.Then, adopt another vacuum vapor deposition equipment, the Al negative electrode of vapour deposition 150 nanometer thickness is made OLED.
Figure BPA00001499588700281
The every kind of compound that is used for OLED passes through in 10 -6Purifying is carried out in the holder vacuum-sublimation.
[comparative example 1] uses existing electroluminescent material to make the OLED device
After forming hole injection layer and hole transmission layer like the identical method of embodiment 1, the DNA of blue light-emitting is placed in another cell of vacuum sediment equipment as matrix, and compd A places in another cell.Two kinds of materials with 100: 1 speed vapour deposition with the thick electroluminescence layer of deposition 30nm on said hole transmission layer.
Figure BPA00001499588700282
Then,, use the thick Al negative electrode of another vacuum sediment equipment vapour deposition 150nm, to make OLED according to after embodiment 1 identical mode forms electron transfer layer and electron injecting layer.
[comparative example 2] uses existing electroluminescent material to make the OLED device
After forming hole injection layer and hole transmission layer like the identical method of embodiment 1, the DNA of blue light-emitting is placed in another cell of vacuum sediment equipment as matrix, and compd B places in another cell.Two kinds of materials with 100: 1 speed vapour deposition with the thick electroluminescence layer of deposition 30nm on said hole transmission layer.
Figure BPA00001499588700283
Then,, use the thick Al negative electrode of another vacuum sediment equipment vapour deposition 150nm, to make OLED according to after embodiment 1 identical mode forms electron transfer layer and electron injecting layer.
At 1000cd/m 2The luminous efficiency of the OLED equipment of making in conditioned measurement embodiment 1-7 and comparative example 1 and 2.The result lists in table 2.
Table 2
Figure BPA00001499588700291
?
As shown in table 2, organic electroluminescent compounds of the present invention is compared existing electroluminescent compounds pure blue is provided.Especially, compound 2 efficient of comparing existing electroluminescent material (compd B) has improved 38%.As said, organic electroluminescent compounds of the present invention can be used as blue emitting material, aspect brightness that has full color OLED now and the watt consumption advantage to be provided.

Claims (10)

1. the organic electroluminescent compounds of a chemical formula (1) expression:
Figure FPA00001499588600011
Wherein
A representes hydrogen or
Figure FPA00001499588600012
Ar 1And Ar 2Represent chemical bond, (C6-C60) arylidene separately or comprise heteroatomic (C2-C60) inferior heteroaryl of one or more N of being selected from, O and S, the carbon atom of wherein said inferior heteroaryl also can be replaced by Se;
Z 1To Z 5At least one and Z 11To Z 15At least one be nitrogen-atoms, remaining is carbon atom, wherein nitrogen-atoms does not have substituting group;
R 1To R 5And R 11To R 15Represent hydrogen, deuterium, (C1-C60) alkyl, (C3-C60) naphthenic base, (C6-C60) aryl, (C2-C60) heteroaryl, (C1-C60) alkoxyl group, (C6-C60) aryloxy, list-or two (C1-C60) alkylamino, list-or two (C6-C60) arylamino, (C6-C60) aryl (C1-C60) alkylamino, three (C1-C60) alkyl silyl, two (C1-C60) alkyl (C6-C60) aryl silyl or three (C6-C60) aryl silyl, wherein R independently 1To R 5Or R 11To R 15Each can be through being with or without condensed ring (C3-C60) alkylidene group or (C3-C60) alkenylene be connected to adjacent substituting group and form condensed ring, the carbon atom of said alkylidene group also can be by O, S or NR 21Replace, and the CH of alkenylene also can be replaced by N;
R 21Expression hydrogen, deuterium, (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxyl group, morpholino, thiomorpholine generation, piperidyl, the heteroatomic 5-that comprises one or more N of being selected from, O and S or the first Heterocyclylalkyl of 6-, (C3-C60) naphthenic base, adamantyl, halogen, cyanic acid, (C6-C60) aryl, (C2-C60) heteroaryl, three (C1-C60) alkyl silyl, two (C1-C60) alkyl (C6-C60) aryl silyl or three (C6-C60) aryl silyl;
X and Y represent independently chemical bond ,-(CR 31R 32) n-,-N (R 33)-,-Si (R 34) (R 35)-,-O-,-S-,-Se-,-P (R 36)-or-(R 37) C=C (R 38)-, wherein n is the integer of 1-4;
R 31To R 38Represent hydrogen, deuterium, (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxyl group, morpholino, thiomorpholine generation, piperidyl, the heteroatomic 5-that comprises one or more N of being selected from, O and S or 6-unit Heterocyclylalkyl, (C3-C60) naphthenic base, adamantyl, halogen, cyanic acid, (C6-C60) aryl, (C2-C60) heteroaryl, three (C1-C60) alkyl silyl, two (C1-C60) alkyl (C6-C60) aryl silyl or three (C6-C60) aryl silyl, perhaps R independently 31And R 32, R 34And R 35Perhaps R 37And R 38Can be independently through being with or without condensed ring (C3-C12) alkylidene group or (C3-C12) alkenylene be connected to form volution or condensed ring; And
Ar 1And Ar 2Arylidene or heteroarylidene, and R 1To R 5, R 11To R 15, R 21And R 31To R 38Alkyl; Naphthenic base; Aryl; Heteroaryl; Alkoxyl group; Aryloxy; Alkylamino; Arylamino; Aryl alkyl amino; Trialkylsilkl; Di alkylaryl silyl or diarye silyl also can replace by being selected from following substituent one or more substituting groups: deuterium; (C1-C60) alkyl; Halo (C1-C60) alkyl; (C1-C60) alkoxyl group; Piperidyl; Morpholino; Thiomorpholine generation; Comprise one or more N of being selected from; The heteroatomic 5-of O and S or 6-unit Heterocyclylalkyl; (C3-C60) naphthenic base; Halogen; Cyanic acid; (C6-C60) aryl; (C2-C60) heteroaryl; (C6-C60) aryl (C1-C60) alkyl; (C1-C60) alkyl (C6-C60) aryl; Three (C1-C60) alkyl silyl; Two (C1-C60) alkyl (C6-C60) aryl silyl and three (C6-C60) aryl silyl.
2. organic electroluminescent compounds as claimed in claim 1, said compound is represented by chemical formula (2) or (3):
Figure FPA00001499588600021
Wherein
Wherein X, Y, Ar 1, Ar 2, Z 1To Z 5, Z 11To Z 15, R 1To R 15And R 11To R 15Defined identical with claim 1.
3. organic electroluminescent compounds as claimed in claim 1, wherein Ar 1And Ar 2Represent chemical bond independently or be selected from the arylidene or the inferior heteroaryl of following structure:
Figure FPA00001499588600031
Wherein
R 41The expression deuterium; (C1-C60) alkyl; Halo (C1-C60) alkyl; (C1-C60) alkoxyl group; Piperidyl; Morpholino; Thiomorpholine generation; Comprise one or more N of being selected from; The heteroatomic 5-of O and S or 6-unit Heterocyclylalkyl; (C3-C60) naphthenic base; Halogen; Cyanic acid; (C6-C60) aryl; (C2-C60) heteroaryl; (C6-C60) aryl (C1-C60) alkyl; (C1-C60) alkyl (C6-C60) aryl; Three (C1-C60) alkyl silyl; Two (C1-C60) alkyl (C6-C60) aryl silyl or three (C6-C60) aryl silyl; And
M is the integer of 0-4.
4. organic electroluminescent compounds as claimed in claim 2; It is characterized in that
Figure FPA00001499588600041
is selected from following structure:
Figure FPA00001499588600042
Wherein
R 31To R 38Represent hydrogen, deuterium, (C1-C60) alkyl, halo (C1-C60) alkyl, (C1-C60) alkoxyl group, morpholino, thiomorpholine generation, piperidyl, the heteroatomic 5-that comprises one or more N of being selected from, O and S or 6-unit Heterocyclylalkyl, (C3-C60) naphthenic base, adamantyl, halogen, cyanic acid, (C6-C60) aryl, (C2-C60) heteroaryl, three (C1-C60) alkyl silyl, two (C1-C60) alkyl (C6-C60) aryl silyl or three (C6-C60) aryl silyl independently; And
R 21To R 28Alkyl; Naphthenic base; Aryl; Heteroaryl; Alkoxyl group; Trialkylsilkl; Di alkylaryl silyl or diarye silyl also can replace by being selected from following substituent one or more substituting groups: deuterium; (C1-C60) alkyl; Halo (C1-C60) alkyl; (C1-C60) alkoxyl group; Piperidyl; Morpholino; Thiomorpholine generation; Comprise one or more N of being selected from; The heteroatomic 5-of O and S or 6-unit Heterocyclylalkyl; (C3-C60) naphthenic base; Halogen; Cyanic acid; (C6-C60) aryl; (C2-C60) heteroaryl; (C6-C60) aryl (C1-C60) alkyl; (C1-C60) alkyl (C6-C60) aryl; Three (C1-C60) alkyl silyl; Two (C1-C60) alkyl (C6-C60) aryl silyl and three (C6-C60) aryl silyl.
5. organic electroluminescent compounds as claimed in claim 2; It is characterized in that,
Figure FPA00001499588600051
and
Figure FPA00001499588600052
be selected from following structure:
Figure FPA00001499588600053
6. organic electroluminescence device, said device comprises each described organic electroluminescent compounds among the claim 1-5.
7. organic electroluminescence device as claimed in claim 6, said device is by forming with the lower section: first electrode; Second electrode; And insert one or more layers organic layer between said first electrode and second electrode; Wherein said organic layer comprises each described organic electroluminescent compounds among one or more claims 1-5, and one or more matrix of chemical formula (4) or (5) expression:
(Ar 11) c-L 1-(Ar 12) d(4)
(Ar 13) e-L 2-(Ar 14) f(5)
Wherein
L 1Expression (C6-C60) arylidene or (C4-C60) inferior heteroaryl;
L 2The expression anthrylene;
Ar 11To Ar 14Represent hydrogen, deuterium, (C1-C60) alkyl, (C1-C60) alkoxyl group, halogen, (C4-C60) heteroaryl, (C5-C60) naphthenic base or (C6-C60) aryl separately, said Ar 11To Ar 14Naphthenic base; Aryl or heteroaryl also can replace by being selected from following substituent one or more substituting groups: (said substituting group is selected from deuterium by one or more substituting groups; (C1-C60) alkyl; Halo (C1-C60) alkyl; (C1-C60) alkoxyl group; (C3-C60) naphthenic base; Halogen; Cyanic acid; Three (C1-C60) alkyl silyl; Two (C1-C60) alkyl (C6-C60) aryl silyl and three (C6-C60) aryl silyl) replace or unsubstituted (C6-C60) aryl or (C4-C60) heteroaryl; Deuterium; (C1-C60) alkyl; Halo (C1-C60) alkyl; (C1-C60) alkoxyl group; (C3-C60) naphthenic base; Halogen; Cyanic acid; Three (C1-C60) alkyl silyl; Two (C1-C60) alkyl (C6-C60) aryl silyl and three (C6-C60) aryl silyl; And
C, d, e and f are the integer of 0-4 independently.
8. organic electroluminescence device as claimed in claim 7; It is characterized in that; Said organic layer also comprises one or more compounds that is selected from aromatic amine compound and styryl aromatic amine compound, or is selected from one or more metals of transition metal, lanthanide series metal and d-transition element of organo-metallic, period 4 and period 5 of the 1st family, the 2nd family of the periodic table of elements.
9. organic electroluminescence device as claimed in claim 7 is characterized in that, said organic electroluminescence device emission white light is because said organic layer comprises the organic electro luminescent layer of one or more layers emission blue light, ruddiness or green glow simultaneously.
10. organic electroluminescence device as claimed in claim 7 is characterized in that said organic layer comprises electroluminescence layer and charge generation layer.
CN2010800349455A 2009-06-02 2010-05-31 Novel organic electroluminescent compounds and organic electroluminescent device using the same Pending CN102575155A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
KR1020090048729A KR20100130068A (en) 2009-06-02 2009-06-02 Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR10-2009-0048729 2009-06-02
PCT/KR2010/003457 WO2010140802A1 (en) 2009-06-02 2010-05-31 Novel organic electroluminescent compounds and organic electroluminescent device using the same

Publications (1)

Publication Number Publication Date
CN102575155A true CN102575155A (en) 2012-07-11

Family

ID=43297885

Family Applications (1)

Application Number Title Priority Date Filing Date
CN2010800349455A Pending CN102575155A (en) 2009-06-02 2010-05-31 Novel organic electroluminescent compounds and organic electroluminescent device using the same

Country Status (5)

Country Link
JP (1) JP2012528853A (en)
KR (1) KR20100130068A (en)
CN (1) CN102575155A (en)
TW (1) TW201105778A (en)
WO (1) WO2010140802A1 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102120891B1 (en) 2013-02-22 2020-06-10 삼성디스플레이 주식회사 Heterocyclic compound and organic light emitting device comprising the same

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002172864A (en) * 2000-09-28 2002-06-18 Fuji Photo Film Co Ltd 2,2'-crosslinking biphenyl compound, optical information recording medium and method for recording
US20030052311A1 (en) * 2001-07-06 2003-03-20 Yoshio Inagaki Two-photon absorption composition
US20070098233A1 (en) * 2003-10-22 2007-05-03 Academia Sinica Cancer cell detecting devices
KR20090018503A (en) * 2007-08-17 2009-02-20 삼성전자주식회사 Oxadiazole derivative containing compound and organic light emitting device comprising the same
CN101386602A (en) * 2008-10-29 2009-03-18 华南理工大学 S-triazine derivates with white light and preparation method and application thereof
CN101486902A (en) * 2009-03-02 2009-07-22 西安近代化学研究所 Organic electroluminescent blue luminescence compound
CN101671291A (en) * 2008-06-25 2010-03-17 葛来西雅帝史派有限公司 Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN102099435A (en) * 2008-07-18 2011-06-15 巴斯夫欧洲公司 Azapyrenes for electronic applications

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3991049A (en) * 1967-07-14 1976-11-09 Ciba-Geigy Ag Aromatic compounds containing ethylene double bonds, processes for their manufacture and use
CH523909A (en) * 1969-01-09 1972-06-15 Ciba Geigy Ag Process for the production of heterocyclic compounds containing ethylene double bonds and their use as optical brighteners outside the textile industry
DE2850585A1 (en) * 1978-11-22 1980-06-04 Hoechst Ag PHOTOPOLYMERIZABLE MIXTURE
JP2767113B2 (en) * 1988-10-17 1998-06-18 株式会社リコー Ink sheet for thermal transfer recording
US5859251A (en) * 1997-09-18 1999-01-12 The United States Of America As Represented By The Secretary Of The Air Force Symmetrical dyes with large two-photon absorption cross-sections
JP2003020469A (en) * 2001-07-06 2003-01-24 Fuji Photo Film Co Ltd Biphoton absorption composition
JP2004292436A (en) * 2003-03-07 2004-10-21 Dainippon Printing Co Ltd Organic compound and organic electroluminescent element
EP1727396A4 (en) * 2004-03-19 2009-08-26 Idemitsu Kosan Co Organic electroluminescent device
CN1887883A (en) * 2005-06-27 2007-01-03 中国科学院理化技术研究所 V-type conjugated light-absorbing organic salt compound and use thereof
KR100788254B1 (en) * 2005-08-16 2007-12-27 (주)그라쎌 Green electroluminescent compounds and organic electroluminescent device using the same
CN101200477A (en) * 2007-08-03 2008-06-18 上海拓引数码技术有限公司 Compound for preparing organic electromechanical phosphorescent material and preparation method thereof
JP5300454B2 (en) * 2008-12-19 2013-09-25 日本化薬株式会社 Dye-sensitized photoelectric conversion element

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002172864A (en) * 2000-09-28 2002-06-18 Fuji Photo Film Co Ltd 2,2'-crosslinking biphenyl compound, optical information recording medium and method for recording
US20030052311A1 (en) * 2001-07-06 2003-03-20 Yoshio Inagaki Two-photon absorption composition
US20070098233A1 (en) * 2003-10-22 2007-05-03 Academia Sinica Cancer cell detecting devices
KR20090018503A (en) * 2007-08-17 2009-02-20 삼성전자주식회사 Oxadiazole derivative containing compound and organic light emitting device comprising the same
CN101671291A (en) * 2008-06-25 2010-03-17 葛来西雅帝史派有限公司 Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN102099435A (en) * 2008-07-18 2011-06-15 巴斯夫欧洲公司 Azapyrenes for electronic applications
CN101386602A (en) * 2008-10-29 2009-03-18 华南理工大学 S-triazine derivates with white light and preparation method and application thereof
CN101486902A (en) * 2009-03-02 2009-07-22 西安近代化学研究所 Organic electroluminescent blue luminescence compound

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
ERNST FISCHER: "CONFORMATIONAL EQUILIBRIA IN TRANS 1,2-DIARYLETHYLENES MANIFESTED IN THEIR EMISSION SPECTRA PART III (la) PYRIDYL AND QUINOLYL DERIVATIVES", 《BULL. SOC. CHIM. BELG.》, vol. 88, 31 December 1979 (1979-12-31), pages 889 - 895 *
HONG-PING ZHOU等: "Synthesis, Crystal Structures and Photoluminescence of Mercury( II ) Complexes with Two Homologous Novel Functional Rigid Ligands", 《EUR. J. INORG. CHEM》, 31 December 2005 (2005-12-31), pages 4976 - 4984 *
JEAN-PAUL PAUCHARD等: "Anil synthesis. 17. Preparation of styryl derivatives of 2-phenyl-4H-1,2,4-triazolo[1,5-a]pyridine", 《HELVETICA CHIMICA ACTA》, vol. 61, no. 1, 31 December 1978 (1978-12-31), XP002424345, DOI: 10.1002/hlca.19780610115 *
KURT BURDESKA等: "Anil synthesis. Part 23. Preparation of styryl and stilbenyl derivatives of pyrimidines", 《HELVETICA CHIMICA ACTA》, vol. 64, no. 1, 31 December 1981 (1981-12-31) *
PANAGIOTIS D. VELLIS等: "New divinylene trimers with triphenylpyridine segments: Synthesis, photophysics, electrochemical and electroluminescent properties", 《SYNTHETIC METALS》, vol. 158, 21 July 2008 (2008-07-21), pages 854 - 860, XP025804221, DOI: 10.1016/j.synthmet.2008.06.002 *
PANAGIOTIS D. VELLIS等: "Synthesis of Terpyridine Ligands and Their Complexation with Zn2+ and Ru2+ for Optoelectroni c Applications", 《JOURNAL OF POLYMER SCIENCE: PART A: POLYMER CHEMISTRY》, vol. 46, 31 December 2008 (2008-12-31), pages 7702 - 7712, XP008119410, DOI: 10.1002/pola.23073 *
VALÉRIE LEBRET等: "Synthesis and Characterization of Fluorescently Doped Mesoporous Nanoparticles for Two-Photon Excitation", 《CHEM. MATER.》, vol. 20, 4 March 2008 (2008-03-04), pages 2174 - 2183 *
ZHANG XIAN等: "Synthesis and Nonlinear Optical Properties of a New A-π-A Two-Photon Compound Utilizing Dibenzothiophene as Center", 《CHINESE JOURNAL OF CHEMISTRY》, vol. 25, 31 December 2007 (2007-12-31) *

Also Published As

Publication number Publication date
TW201105778A (en) 2011-02-16
WO2010140802A1 (en) 2010-12-09
KR20100130068A (en) 2010-12-10
JP2012528853A (en) 2012-11-15

Similar Documents

Publication Publication Date Title
CN101805266B (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN101671291B (en) Organic electroluminescent compounds and organic electroluminescent device using the same
JP5406305B2 (en) Electroluminescent device using electroluminescent compound as luminescent material
CN102918134B (en) Organic electroluminescent compounds and the organic electroluminescence device using the compound
CN102449109B (en) The organic electroluminescent device of novel organic electroluminescent compounds and this compound of use
CN104080882B (en) The organic electroluminescence device of organic electroluminescent compounds and this compound of use
CN101184822B (en) Electroluminescent device
CN102933531B (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN101784635B (en) Material for organic photoelectric device, and organic photoelectric device including the same
CN102933530A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN104271582A (en) Novel organic electroluminescence compounds and organic electroluminescence device containing the same
CN104066739A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN103298800A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN103221406A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN102625806A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN103249800A (en) Novel compounds for organic electronic material and organic electroluminescent device using the same
CN103703003A (en) Novel compounds for organic electronic material and organic electroluminescent device using the same
CN103827119A (en) Novel organic electroluminescence compounds and organic electroluminescence device using the same
JP2010059158A (en) New organic electroluminescent compound and organic electroluminescent device produced by using the same
CN103228661A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN102449110A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN102803436A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN102482572A (en) Novel compounds for organic electronic material and organic electronic device using the same
CN103732590A (en) Novel compounds for organic electronic material and organic electroluminescent device using same
CN101668730A (en) New diamine derivatives and organic electronic device using the same

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C02 Deemed withdrawal of patent application after publication (patent law 2001)
WD01 Invention patent application deemed withdrawn after publication

Application publication date: 20120711