CN102449110A - 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
CN102449110A
CN102449110A CN2010800250539A CN201080025053A CN102449110A CN 102449110 A CN102449110 A CN 102449110A CN 2010800250539 A CN2010800250539 A CN 2010800250539A CN 201080025053 A CN201080025053 A CN 201080025053A CN 102449110 A CN102449110 A CN 102449110A
Authority
CN
China
Prior art keywords
substituent
aryl
alkyl
organic electroluminescent
carbonyl
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
CN2010800250539A
Other languages
Chinese (zh)
Inventor
金荣佶
李孝姃
赵英俊
权赫柱
金奉玉
金圣珉
尹胜洙
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 CN102449110A publication Critical patent/CN102449110A/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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • 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
    • C07D213/16—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 containing only one pyridine ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
    • 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
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
    • C07D265/38—[b, e]-condensed with two six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings
    • C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—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
    • 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
    • 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
    • C07F7/0834—Compounds having one or more O-Si linkage
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • 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
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • 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
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/16—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering
    • H10K71/164—Deposition of organic active material using physical vapour deposition [PVD], e.g. vacuum deposition or sputtering using vacuum deposition

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Quinoline Compounds (AREA)
  • Indole Compounds (AREA)

Abstract

Disclosed are novel organic electroluminescent compounds and organic electroluminescent devices comprising the same. With good luminous efficiency and excellent color purity and life property, the organic electroluminescent compounds according to the invention can be used to manufacture OLED devices having very good operation life.

Description

Novel organic electroluminescent compounds and the organic electroluminescent device that uses this compound
Technical field
The present invention relates to novel organic electroluminescent compounds and the organic electroluminescent device that uses this compound.Specifically, the present invention relates to have electroluminescence characters novelty anthracene derivant and use the organic electroluminescent device of this anthracene derivant as electroluminescent material.
Background technology
Electroluminescent (EL) device is a self-luminous display spare, and in various display devices, electroluminescent device has the advantage of wide visual angle, splendid contrast gradient and the quick speed of response.Easterman Kodak (Eastman Kodak) has at first developed a kind of organic EL device [Appl.Phys.Lett.51,913,1987] in 1987, this device uses low molecule aromatic diamine and aluminum complex as the material that forms electroluminescence layer.
Organic el device is a kind of equipment with following characteristic, and when electric charge was applied to the organic membrane that is formed between electron injection electrode (negative electrode) and the hole injecting electrode (anode), electronics and hole pairing were buried in oblivion also luminous then.Can go up forming device at clear flexible base material (for example plastics).Compare plasma display device and inorganic EL indicating meter, said equipment can be worked under low voltage (being no more than 10V) and lower watt consumption condition, has excellent purity of color simultaneously.Because organic electroluminescent (EL) equipment can have three kinds of colors (green, blue and red), they have thought follow-on full color display equipment.
The most important factor in the luminous efficiency of decision organic EL device, life-span etc. is an electroluminescent material.Require this electroluminescent material to have following character; Comprise that material should have high electroluminescent quantum yield (quantum yield) and high electronics and hole mobility down solid-state; During vacuum vapor deposition, be difficult for decomposing, and can form all even stable film.
Organic el device is made up of anode/HIL/HTL/EML/ETL/EIL/ negative electrode.The color of the light that sends from organic electroluminescent device (blue, green, redness) can realize based on how forming electroluminescence layer (EML).
Said electroluminescent material can be divided into substrate material and dopant material according to its function.Usually known, the device structure with the most excellent EL performance can be used on the EL layer that the doping doping agent prepares in the matrix and makes.At present, exploitation has high-level efficiency and long-life organic el device becomes the instant target, waits until the required EL performance of large size OLED display pannel in considering, special instant is that the material that conventional EL material has a lot of EL performances is compared in exploitation.
Meanwhile; System below people have developed also is widely used as green fluorescent material: in this system; With coumarin derivatives (compound d; C545T), quinacridone derivative (Verbindung), DPT (compound f) etc. extremely go among the Alq (matrix) as doping agent greater than 20% doped in concentrations profiled with percentum.Although conventional electroluminescent material has good initial luminous efficiency performance at actual application level,, there is very big problem in the life-span aspect of these materials, and starting efficiency can significantly reduce as time passes.Therefore, the application of these materials in the high-performance panel of large-size screen is restricted.
In addition, because prepared OLED equipment can not obtain gratifying equipment life of level, the substrate material that therefore needs exploitation to have a lot of stability and performance.
Summary of the invention
Technical problem
Therefore, the objective of the invention is to overcome the problems referred to above and the organic electroluminescent compounds that comprises excellent skeleton is provided, obtain better luminous efficiency, equipment life and suitable chromaticity coordinates to compare the conventional substrate material.
Another object of the present invention provides has high-level efficiency and long-life organic electroluminescent device, and it uses this organic electroluminescent compounds as electroluminescent material.
The method of dealing with problems
In order to achieve the above object, novel organic electroluminescent compounds produced according to the present invention.These compounds can be used as the electroluminescent material that organic electroluminescent device uses, in particular as electroluminescent matrix, and preferably green matrix.Compound of the present invention makes organic electroluminescent device have the efficient of raising, the WV and the improved stability of reduction.
The invention provides the organic electroluminescent compounds that Chemical formula 1 is represented:
[Chemical formula 1]
Figure BPA00001479921300031
In the formula:
L 1And L 2Represent chemical bond independently, be with or without substituent (C6-C30) arylidene, be with or without substituent (C3-C30) inferior heteroaryl; Be with or without substituent 5-to the inferior Heterocyclylalkyl of 7-unit; Replace with one or more aromatic ring condensed or unsubstituted 5-to the first inferior Heterocyclylalkyl of 7-, be with or without substituent (C3-C30) cycloalkylidene, with one or more aryl-fused replacements or unsubstituted (C3-C30) cycloalkylidene; Be with or without substituent inferior adamantyl; Be with or without substituent (C7-C30) inferior bicyclic alkyl, be with or without substituent (C2-C30) alkenylene, be with or without substituent (C2-C30) alkynylene; Be with or without substituent (C6-C30) aryl (C1-C30) alkylidene group; Be with or without substituent (C1-C30) alkylene sulfenyl (alkylenethio), be with or without substituent (C1-C30) alkylene oxide group (alkyleneoxy), be with or without substituent (C6-C30) inferior aryloxy (aryleneoxy); Be with or without substituent (C6-C30) inferior arylthio (arylenethio) ,-O-or-S-;
R 1To R 4And Ar 1Represent hydrogen independently, deuterium, halogen; Be with or without substituent (C1-C30) alkyl, be with or without substituent (C6-C30) aryl, with one or more substituent (C3-C30) Cycloalkylfused replacement or unsubstituted (C6-C30) aryl of being with or without; Be with or without substituent (C3-C30) heteroaryl, be with or without substituent 5-or 7-unit Heterocyclylalkyl, replace with one or more aromatic ring condensed or unsubstituted 5-to the first Heterocyclylalkyl of 7-; Be with or without substituent (C3-C30) naphthenic base; Replace or unsubstituted (C3-C30) naphthenic base with one or more aromatic ring condensed, be with or without substituent adamantyl, be with or without substituent (C7-C30) bicyclic alkyl; Cyanic acid, NR 11R 12, BR 13R 14, PR 15R 16, P (=O) R 17R 18[R wherein 11To R 18Expression is with or without substituent (C1-C30) alkyl independently, is with or without substituent (C6-C30) aryl, or is with or without substituent (C3-C30) heteroaryl]; Be with or without substituent three (C1-C30) alkyl silyl, be with or without substituent two (C1-C30) alkyl (C6-C30) aryl silyl, be with or without substituent three (C6-C30) aryl silyl; Be with or without substituent (C6-C30) aryl (C1-C30) alkyl, be with or without substituent (C1-C30) alkoxyl group, be with or without substituent (C1-C30) alkylthio; Be with or without substituent (C6-C30) aryloxy, be with or without substituent (C6-C30) arylthio, be with or without substituent (C1-C30) alkoxy carbonyl; Be with or without substituent (C1-C30) alkyl-carbonyl, be with or without substituent (C6-C30) aryl carbonyl, be with or without substituent (C2-C30) thiazolinyl; Be with or without substituent (C2-C30) alkynyl, be with or without substituent (C6-C30) aryloxycarbonyl, be with or without substituent (C1-C30) alkoxy-carbonyl oxy; Be with or without substituent (C1-C30) alkyl-carbonyl oxygen base (alkylcarbonyloxy); Be with or without substituent (C6-C30) aryl carbonyl oxygen base, be with or without substituent (C6-C30) aryloxycarbonyl oxygen base, carboxyl; Nitro
Figure BPA00001479921300041
, or hydroxyl, (C3-C30) alkylidene group that perhaps they separately can be through being with or without condensed ring or (C3-C30) alkenylene be connected to adjacent substituting group to form alicyclic ring or monocycle or many cyclophanes ring;
W representes-(CR 51R 52) m-,-(R 51) C=C (R 52)-,-N (R 53)-,-S-,-O-,-Si (R 54) (R 55)-,-P (R 56)-,-P (=O) (R 57)-,-C (=O)-or-B (R 58)-, and R 51To R 58And R 61To R 63Definition and R 1To R 4Identical;
Each self-contained one or more B that are selected from of said Heterocyclylalkyl and heteroaryl, N, O, S, P (=O), the heteroatoms of Si and P; And
M representes 1 or 2 integer.
Described herein comprising " alkyl ", " alkyl ", " alkoxyl group " and other substituting groups of part comprised a straight chain and a chain portion.
Term described herein " aryl " expression is removed the organic group that obtains behind the Wasserstoffatoms by aromatic hydrocarbon.Aryl can be monocycle or condensed ring system, and each ring of aryl suitably comprises 4-7, preferred 5-6 annular atoms.Can comprise that also two or more aryl are through singly-bound bonded structure.Object lesson comprises phenyl, naphthyl, xenyl (biphenyl), anthryl, indenyl, fluorenyl, phenanthryl (phenanthryl), benzo [9; 10] phenanthryl (triphenylenyl), pyrenyl 、 perylene base (perylenyl),
Figure BPA00001479921300042
base (chrysenyl), naphthacenyl (naphthacenyl), fluoranthene base (fluoranthenyl) etc., but be not limited thereto.Naphthyl can be 1-naphthyl or 2-naphthyl, and anthryl can be 1-anthryl, 2-anthryl or 9-anthryl, and fluorenyl can be any in 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and the 9-fluorenyl.
Comprise 1-4 in term as herein described " heteroaryl " the expression aromatic nucleus skeletal atom and be selected from B, N, O, S, P (=O), the aryl that the heteroatoms of Si and P and remaining aromatic nucleus skeletal atom are carbon atom.Said heteroaryl can be 5-or 6-unit's bicyclic heteroaryl or with one or more phenyl ring condensed polyheteroaromatics, and can be fractional saturation.Also can comprise and have one or more structures through singly linked heteroaryl.Said heteroaryl can comprise divalent aryl, its heteroatoms oxidation or quaternized formation N-oxide compound, quaternary ammonium salt etc.Concrete example comprises for example furyl of bicyclic heteroaryl; Thienyl; Pyrryl; Imidazolyl; Pyrazolyl; Thiazolyl; Thiadiazolyl group; Isothiazolyl; Different
Figure BPA00001479921300051
azoles base;
Figure BPA00001479921300052
azoles base;
Figure BPA00001479921300053
di azoly; Triazinyl; The tetrazine base; Triazolyl; Tetrazyl; Furazan base (furazanyl); Pyridyl; Pyrazinyl; Pyrimidyl; Pyridazinyl; Polyheteroaromatic is benzofuryl for example; Benzothienyl; Isobenzofuran-base; Benzimidazolyl-; Benzothiazolyl; The benzisothiazole base; Benzisoxa
Figure BPA00001479921300054
azoles base; Benzo
Figure BPA00001479921300055
azoles base; Pseudoindoyl; Indyl; Indazolyl; The diazosulfide base; Quinolyl; Isoquinolyl; Cinnolines base (cinnolinyl); Quinazolyl; Quinoxalinyl (quinoxalinyl); Carbazyl; Phenanthridinyl (phenanthridinyl) and benzo dioxolyl (benzodioxolyl); And corresponding N-oxide compound (for example pyridyl N-oxide compound, quinolyl N-oxide compound); And quaternary ammonium salt, but be not limited to this.
In the present invention; (C1-C30) alkyl, three (C1-C30) alkyl silyl, two (C1-C30) alkyl (C6-C30) aryl silyl, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkoxyl group, (C1-C30) alkylthio, (C1-C30) alkoxy carbonyl, (C1-C30) alkyl-carbonyl, (C1-C30) alkoxy-carbonyl oxy or (C1-C30) carbonatoms of the alkyl of alkyl-carbonyl oxygen base can be defined as 1-20 carbon atom, or 1-10 carbon atom.(C6-C30) aryl, two (C1-C30) alkyl (C6-C30) aryl silyl, three (C6-C30) aryl silyl; (C6-C30) aryl (C1-C30) alkyl, (C6-C30) aryloxy, (C6-C30) arylthio; (C6-C30) aryl carbonyl; (C6-C30) aryloxycarbonyl, (C6-C30) aryl carbonyl oxygen base or (C6-C30) carbonatoms of the aryl of aryloxycarbonyl oxygen base can be defined as 6-20 carbon atom, or 6-12 carbon atom.(C3-C30) carbonatoms of the heteroaryl in the heteroaryl can be defined as 4-20 carbon atom, or 4-12 carbon atom.(C3-C30) carbonatoms of the naphthenic base in the naphthenic base can be defined as 3-20 carbon atom, or 3-7 carbon atom.(C2-C30) carbon atom of the alkenyl or alkynyl of alkenyl or alkynyl can be defined as 2-20 carbon atom or 2-10 carbon atom.
And in the present invention, term " replaces or does not replace, perhaps be with or without substituting group " expression and has one or more substituting groups that are independently selected from following group: deuterium; Halogen is with or without (C1-C30) alkyl of halogenic substituent, and (C6-C30) aryl is with or without (C3-C30) heteroaryl of (C6-C30) aryl substituent; Comprise one or more B of being selected from, N, O, S; P (=O), the heteroatomic 5-of Si and P is to 7-unit Heterocyclylalkyl, with one or more aromatic ring condensed 5-to 7-first Heterocyclylalkyl, (C3-C30) naphthenic base; With one or more aromatic ring condensed (C6-C30) naphthenic base, three (C1-C30) alkyl silyl, two (C1-C30) alkyl (C6-C30) aryl silyl, three (C6-C30) aryl silyl; Adamantyl, (C7-C30) bicyclic alkyl, (C2-C30) thiazolinyl, (C2-C30) alkynyl; Cyanic acid, carbazyl, NR 21R 22, BR 23R 24, PR 25R 26, P (=O) R 27R 28[R wherein 21To R 28Represent (C1-C30) alkyl, (C6-C30) aryl or (C3-C30) heteroaryl independently], (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl; (C1-C30) alkoxyl group, (C1-C30) alkylthio, (C6-C30) aryloxy, (C6-C30) arylthio; (C1-C30) alkoxy carbonyl, (C1-C30) alkyl-carbonyl, (C6-C30) aryl carbonyl, (C6-C30) aryloxycarbonyl; (C1-C30) alkoxy-carbonyl oxy, (C1-C30) alkyl-carbonyl oxygen base, (C6-C30) aryl carbonyl oxygen base, (C6-C30) aryloxycarbonyl oxygen base; Carboxyl, nitro and hydroxyl, perhaps adjacent substituting group is joined together to form ring.
In chemical formula (1), L 1And L 2Can be independently selected from chemical bond, arylidene (for example phenylene, naphthylidene, anthrylene, biphenylene, fluorylidene, inferior benzo [9,10] phenanthryl, inferior fluoranthene base, Asia
Figure BPA00001479921300061
Basic, inferior tetrad phenyl (terphenylene), phenanthrylene (phenanthrylene), inferior pyrenyl (pyrenylene) and inferior perylene base (perylenylene) etc.); And inferior heteroaryl (for example pyridylidene, inferior pyrazinyl, furylidene, inferior thienyl, inferior seleno phenyl (selenophenylene), quinolinediyl, inferior quinoxalinyl, inferior phenanthroline base (phenanthrolinylene) etc., but be not limited thereto.These groups also can be like the said further replacement of chemical formula (1).
R 1To R 4And Ar 1Can be selected from independently of one another: aryl, for example phenyl, naphthyl, anthryl, xenyl, fluorenyl, phenanthryl, pyrenyl He perylene base; Heteroaryl, for example pyridyl, pyrazinyl, furyl, thienyl, seleno phenyl (selenophenyl), quinolyl, quinoxalinyl, phenanthroline base (phenanthrolinyl), carbazyl and benzo piperidyl; With Cycloalkylfused aryl, for example tetralyl; With one or more aromatic ring condensed heterocycle alkyl, for example the benzo piperidines is for (benzopiperidino), dibenzo morpholino (dibenzomorpholino), dibenzo azepine
Figure BPA00001479921300062
(dibenzoazepino); NR 71R 72, BR 73R 74, PR 75R 76And P (=O) R 77R 78[wherein, R 71To R 78Expression replaces or unsubstituted (C1-C30) alkyl independently, replaces or unsubstituted (C6-C30) aryl or replacement or unsubstituted (C3-C30) heteroaryl], but be not limited thereto, and each group can further replace by substituting group, concrete shown in chemical formula (1).
Each group
Figure BPA00001479921300071
Can be enumerated as following structure:
Wherein, R 51To R 58Expression replaces or unsubstituted (C1-C30) alkyl independently; Replace or unsubstituted (C6-C30) aryl; Perhaps replace or unsubstituted (C3-C30) heteroaryl, (C3-C30) alkylidene group that perhaps they separately can be through being with or without condensed ring or (C3-C30) alkenylene be connected to adjacent substituting group and form alicyclic ring or monocycle or many cyclophanes ring.
The object lesson of organic electroluminescent compounds of the present invention can be referring to following compound, but is not limited thereto.
Figure BPA00001479921300101
Figure BPA00001479921300111
Figure BPA00001479921300121
Figure BPA00001479921300131
The example for preparing the method for organic electroluminescent compounds of the present invention can be referring to reaction process (1) or (2), but are not limited thereto.
Reaction process 1
Figure BPA00001479921300132
Reaction process 2
Figure BPA00001479921300141
In above-mentioned reaction process, R 1To R 4, L 1, L 2And Ar 1Definition referring to chemical formula (1).
The present invention also provides a kind of organic electroluminescent device, and it is made up of first electrode, second electrode and the organic layer of one deck at least that inserts between said first electrode and second electrode; Wherein said organic layer comprises the organic electroluminescent compounds of one or more chemical formulas (1) expression.Said organic electroluminescent compounds can be used as the substrate material of electroluminescence layer.
The characteristic of organic electroluminescent of the present invention (EL) device is, said organic layer comprises the EL layer, and said EL layer comprises one or more organic electroluminescent compounds and one or more EL doping agents of chemical formula (1) expression.Be applied to the not concrete restriction of doping agent of organic electroluminescent device of the present invention, but be preferably selected from the compound of chemical formula (2) or (3) expression:
Figure BPA00001479921300142
In the formula:
L representes to be with or without substituent (C6-C30) arylidene, is with or without substituent (C3-C30) inferior heteroaryl;
R 151To R 154Represent hydrogen independently, deuterium, halogen; Be with or without substituent (C1-C30) alkyl, be with or without substituent (C6-C30) aryl, be with or without substituent (C3-C30) heteroaryl; Be with or without substituent 5-to 7-unit Heterocyclylalkyl, replace with one or more aromatic ring condensed or unsubstituted 5-to the first Heterocyclylalkyl of 7-, be with or without substituent (C3-C30) naphthenic base; Replace or unsubstituted (C3-C30) naphthenic base with one or more aromatic ring condensed, be with or without substituent adamantyl, be with or without substituent (C7-C30) bicyclic alkyl; Cyanic acid, NR 41R 42, BR 43R 44, PR 45R 46, P (=O) R 47R 48[R wherein 41To R 48Expression is with or without substituent (C1-C30) alkyl independently, is with or without substituent (C6-C30) aryl, or is with or without substituent (C3-C30) heteroaryl]; Be with or without substituent three (C1-C30) alkyl silyl, be with or without substituent two (C1-C30) alkyl (C6-C30) aryl silyl, be with or without substituent three (C6-C30) aryl silyl; Be with or without substituent (C6-C30) aryl (C1-C30) alkyl, be with or without substituent (C1-C30) alkoxyl group, be with or without substituent (C1-C30) alkylthio; Be with or without substituent (C6-C30) aryloxy, be with or without substituent (C6-C30) arylthio, be with or without substituent (C1-C30) alkoxy carbonyl; Be with or without substituent (C1-C30) alkyl-carbonyl, be with or without substituent (C6-C30) aryl carbonyl, be with or without substituent (C2-C30) thiazolinyl; Be with or without substituent (C2-C30) alkynyl; Be with or without substituent (C6-C30) aryloxycarbonyl, be with or without substituent (C1-C30) alkoxy-carbonyl oxy, be with or without substituent (C1-C30) alkyl-carbonyl oxygen base (alkylcarbonyloxy); Be with or without substituent (C6-C30) aryl carbonyl oxygen base; Be with or without substituent (C6-C30) aryloxycarbonyl oxygen base, carboxyl, nitro; Or hydroxyl, (C3-C30) alkylidene group that perhaps they separately can be through being with or without condensed ring or (C3-C30) alkenylene be connected to adjacent carbons and form condensed ring; And
Each self-contained one or more B that are selected from of said Heterocyclylalkyl and heteroaryl, N, O, S, P (=O), the heteroatoms of Si and P.
Said electroluminescence layer representes to take place electroluminescent layer, and it can be that individual layer is perhaps by two-layer or a plurality of folded layer by layer multilayers of forming.When structure according to the present invention uses matrix-doping agent mixture, can confirm to have obtained the luminous efficiency that significantly improves, this is because used electroluminescent matrix of the present invention.This can obtain through the doping content of 0.5-10 weight %.Matrix phase of the present invention has higher hole and electron conductivity and excellent stability of material than conventional substrate material, and improved equipment life and luminous efficiency are provided.
The example of the dopant compound of chemical formula (3) expression can be referring to korean patent application 10-2009-0023442.More preferably, they can be selected from following structure, but are not limited thereto.
Figure BPA00001479921300161
Except the organic electroluminescent compounds of chemical formula (1) expression, organic electroluminescent device of the present invention can comprise that also one or more are selected from the compound of aromatic amine compound and styryl aromatic amine compound.The example of said aromatic amine compound or styryl aromatic amine compound is referring to korean patent application 10-2008-0123276,10-2008-0107606 and 10-2008-0118428, but be not limited thereto.
In organic electroluminescent device of the present invention; Said organic layer also can comprise metal or its complex compound of one or more organo-metallic that are selected from 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, and the organic electroluminescent compounds of one or more chemical formulas (1) expression.Organic layer can comprise electroluminescence layer and charge generation layer simultaneously.
Except the organic electroluminescent compounds of chemical formula (1) expression, said organic electroluminescent device also can comprise the organic electro luminescent layer of one or more layers emission blue light, green glow or ruddiness, to form the organic electroluminescent device of emission white light.The example of the compound of emission blue light, green glow or ruddiness can be referring to korean patent application 10-2008-0123276,10-2008-0107606 and 10-2008-0118428, but be not limited thereto.In organic electroluminescent device of the present invention, preferably one or more layers layer (below be called " upper layer ") that is selected from chalcogenide layer, metal halide and metal oxide layer is arranged on the internal surface of at least one side of electrode pair.Especially, preferably the chalkogenide (comprising oxide compound) of silicon and aluminum metal layer is arranged on the anode surface of EL medium layer, metal halide or metal oxide layer is arranged on the cathode surface layer of EL medium layer.Therefore, can obtain job stability.
The example of chalkogenide preferably includes SiO x(1=X=2), AlO x(1=X=1.5), SiON, SiAlON etc.The example of metal halide preferably includes LiF, MgF 2, CaF 2, the fluorochemical of rare earth metal etc.The example of MOX preferably includes Cs 2O, Li 2O, MgO, SrO, BaO, CaO etc.
In organic electroluminescent device of the present invention, also preferably at least one surface of prepared electrode pair, be provided with the mixing zone of electric transmission compound and reductibility doping agent, perhaps the mixing zone of hole transport compound and oxidisability doping agent.Therefore, the electric transmission compound is reduced into negatively charged ion, thereby promotes electronics to inject from the mixing zone and be transferred to the EL medium.In addition, because the hole transport compound oxidation forms positively charged ion, thereby promote the hole to inject and be transferred to the EL 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.
Having white electroluminescence equipment two-layer or more multilayer electroluminescent layer can use the reductibility dopant layer to prepare as charge generation layer.
The advantageous effects of invention
Organic electroluminescent compounds of the present invention has high luminous efficiency and excellent material lifetime characteristic, thus the OLED that preparation has fabulous working life.
Best mode for carrying out the invention
The present invention also can further describe organic electroluminescent compounds of the present invention with reference to representative compound, the electroluminescent properties of its preparation method and prepared equipment, but these embodiment only are used to describe purpose, do not limit scope of the present invention.
[preparation example 1] preparation compound (1)
Figure BPA00001479921300181
Preparation compound (A)
Pack in the double-neck flask 2-methyl-bromobenzoate (40g, 152.6mmol), naphthalene-1-ylboronic acid (31.5g, 183.2mmol) and tetrakis triphenylphosphine palladium [Pd (PPh 3) 4] (8.8g, 7.62mmol).When stirring the mixture, add toluene (1L), add then the 2M solution of potassium carbonate (228mL, 458mmol) and ethanol (228mL).Again with this mixture in 100 ℃ of reflux 5 hours.When reaction was accomplished, the reaction mixture cool to room temperature was with zero(ppm) water and ethyl acetate extraction.Organic layer is used MgSO 4Drying, and desolvate to remove with rotatory evaporator evaporation.Obtain compound (A) (35g, 87%) through column chromatography (hexane and ETHYLE ACETATE are as eluent) purifying.
The preparation of compound (B)
(24g, single neck flask 91.49mmol) vacuumizes inclusion compound (A), and fills with argon gas.After adding THF (1L), said mixture stirred 10 minutes in-75 ℃.(257mL 0.41mol) adds wherein lithium methide (MeLi of 1.6M in the hexane), and the gained mixture stirred 10 minutes in-75 ℃, then in stirring at room 3 hours.When reaction was accomplished, reaction mixture was with zero(ppm) water and ethyl acetate extraction.Organic layer is used MgSO 4Drying, and desolvate to remove with rotatory evaporator evaporation.Obtain compound (B) (20g, 83%) through column chromatography (hexane and ETHYLE ACETATE are as eluent) purifying.
The preparation of compound (C)
(20g adds AcOH (300mL) in single neck flask 76.23mmol), and said mixture stirred 10 minutes in 0 ℃ to inclusion compound (B).Add H 3PO 4(400mL), the gained mixture was in stirring at room 1 hour.When reaction was accomplished, reaction mixture neutralized through adding NaOH, with zero(ppm) water and ethyl acetate extraction.Organic layer is used MgSO 4Drying, and desolvate to remove with rotatory evaporator evaporation.Obtain compound (C) (13.5g, 72%) through column chromatography (hexane and ETHYLE ACETATE are as eluent) purifying.
Preparation compound (D)
(13.5g, single neck flask 55.25mmol) vacuumizes inclusion compound (C), and fills with argon gas.After adding THF (500mL), said mixture stirred 10 minutes in 0 ℃.(19.6g 0.1lmol) adds wherein NBS, and the gained mixture was in stirring at room one day.When reaction was accomplished, reaction mixture was with zero(ppm) water and ethyl acetate extraction.Organic layer is used MgSO 4Drying, and desolvate to remove with rotatory evaporator evaporation.Obtain compound (D) (13g, 73%) through column chromatography (hexane and ETHYLE ACETATE are as eluent) purifying.
Preparation compound (E)
(13g, single neck flask 42.21mmol) vacuumizes inclusion compound (D), and fills with argon gas.After adding THF (500mL), said mixture stirred 10 minutes in-78 ℃.(24.1mL, 60.32mmol), and the gained mixture stirred 1.5 hours in uniform temp with adding n-BuLi (2.5M in hexane) in the said mixture.Then in-78 ℃ add trimethyl borates (6.85mL, 60.32mmol).Stirred these reaction mixtures 30 minutes in-78 ℃, stirred 4 hours under the room temperature then.When reaction was accomplished, reaction mixture was with zero(ppm) water and ethyl acetate extraction.Organic layer is used MgSO 4Drying, and desolvate to remove with rotatory evaporator evaporation.Obtain compound (E) (8g, 69%) through column chromatography (hexane and ETHYLE ACETATE are as eluent) purifying.
Preparation compound (F)
Pack in the double-neck flask 2-chrloroanthracene-9,10 (4aH, 9aH)-diketone (50g, 0.2mol), phenyl-boron dihydroxide (37.6g, 0.3mol) and tetrakis triphenylphosphine palladium (9.5g, 8.24mmol).When stirring the mixture, add toluene, add then the 2M solution of potassium carbonate (500mL, 1.0mol) and ethanol (500mL).Again with this mixture in 120 ℃ of reflux 5 hours.When reaction was accomplished, the reaction mixture cool to room temperature was with zero(ppm) water and ethyl acetate extraction.Organic layer is used MgSO 4Drying, and desolvate to remove with rotatory evaporator evaporation.Obtain compound (F) (56g, 95%) through column chromatography (hexane and ETHYLE ACETATE are as eluent) purifying.
Preparation compound (G)
(50g adds AcOH (1L) in single neck flask 0.17mol), and said mixture stirred 10 minutes to inclusion compound (F).Add H 3PO 2(380g, 5.76mol) and HI (781g, 6.11mol) after, the gained mixture stirred one day in 150 ℃.When reaction was accomplished, reaction mixture filtered the gained solid through adding NaOH solution and HCl neutralization.Said solid joins in the ETHYLE ACETATE, and in 100 ℃ of backflow recrystallizations with separating compound (G) (40g, 90%).
The preparation of compound (H)
(40g, single neck flask 0.15mol) vacuumizes inclusion compound (G), and fills with argon gas.After adding methylene dichloride (500mL), said mixture stirred 10 minutes in 0 ℃.(28g 0.15mol) adds wherein NBS, and the gained mixture was in stirring at room one day.When reaction was accomplished, reaction mixture was with zero(ppm) water and ethyl acetate extraction.Organic layer is used MgSO 4Drying, and desolvate to remove with rotatory evaporator evaporation.Obtain compound (H) (48g, 92%) through column chromatography (hexane and ETHYLE ACETATE are as eluent) purifying.
Preparation compound (I)
Pack in the double-neck flask compound (H) (48g, 0.14mol), compound (E) (43g, 0.15mol) and tetrakis triphenylphosphine palladium (8.3g, 7.2mmol).When stirring the mixture, add toluene, add then the 2M solution of potassium carbonate (720mL, 1.4mol) and ethanol (720mL).Again with this mixture in 120 ℃ of reflux 5 hours.When reaction was accomplished, the reaction mixture cool to room temperature was with zero(ppm) water and ethyl acetate extraction.Organic layer is used MgSO 4Drying, and desolvate to remove with rotatory evaporator evaporation.Obtain compound (I) (60g, 84%) through column chromatography (hexane and ETHYLE ACETATE are as eluent) purifying.
Preparation compound (J)
(60g, single neck flask 0.12mol) vacuumizes inclusion compound (I), and fills with argon gas.After adding methylene dichloride (600mL), said mixture stirred 10 minutes in 0 ℃.(38.7g 0.21mol) adds wherein NBS, and the gained mixture was in stirring at room one day.When reaction was accomplished, reaction mixture was with zero(ppm) water and ethyl acetate extraction.Organic layer is used MgSO 4Drying, and desolvate to remove with rotatory evaporator evaporation.Obtain compound (J) (60g, 86%) through column chromatography (hexane and ETHYLE ACETATE are as eluent) purifying.
The preparation of compound (1)
Pack in the double-neck flask compound (J) (10g, 17.37mmol), phenyl-boron dihydroxide (3.1g, 26.06mmol) and tetrakis triphenylphosphine palladium (1.0g, 0.86mmol).When stirring the mixture, add toluene, add then the 2M solution of potassium carbonate (86mL, 0.17mol) and ethanol (86mL).Again with this mixture in 120 ℃ of reflux 5 hours.When reaction was accomplished, the reaction mixture cool to room temperature was with zero(ppm) water and ethyl acetate extraction.Organic layer is used MgSO 4Drying, and desolvate to remove with rotatory evaporator evaporation.Obtain compound (1) (8.5g, 85%) through column chromatography (hexane and ETHYLE ACETATE are as eluent) purifying.
Prepare organic electroluminescent compounds (compound 1-120) according to preparing example 1 identical method, its 1H NMR and MS/FAB data rows are in following table 1.
[table 1]
Figure BPA00001479921300221
Figure BPA00001479921300231
[embodiment 1] uses electroluminescent compounds of the present invention to make OLED
Use electroluminescent material of the present invention to make OLED equipment.
At first, (15 Ω/) (available from SCP company) 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; Will by following chemical structural formula represent 4.4 ' 4 " three (N; N-(2-naphthyl)-phenyl amino) triphenylamine (2-TNATA) places the cell (cell) of vacuum vapor deposition equipment, is vented to indoor vacuum tightness then and reaches 10 -6Holder.Cell is applied electric current, makes 2-TNATA evaporation, thus on the ITO substrate hole injection layer of vapour deposition 60 nano thickness.
Then, in another cell of this vacuum vapor deposition equipment, add N, N '-two (Alpha-Naphthyl)-N; N '-phenylbenzene-4; 4 '-diamines (NPB) (its structure is stated as follows), to cell apply electric current with the evaporation NPB, thereby on hole injection layer the hole transport layer of vapour deposition 20 nano thickness.
Figure BPA00001479921300241
After forming hole injection layer and hole transport layer, vapour deposition electroluminescence layer (5) is specific as follows in the above.In a cell of vacuum vapor deposition equipment, add compound of the present invention (1) as matrix, compound (A) joins in another cell as doping agent.Two kinds of materials evaporate with different speed, thereby the doping content of 2-5 weight % is provided, and this doping content is a benchmark in said matrix.Therefore, the thick electroluminescence layer of vapour deposition 30nm on said hole transmission layer.
Figure BPA00001479921300242
Then, three (oxines) that following structural formula is represented close aluminium (III) (Alq) vapour deposition be the electron transfer layer of 20 nanometer thickness, with oxine close lithium (lithium quinolate) (Liq) vapour deposition be the electron injecting layer of 1-2 nanometer thickness.Then, adopt another vacuum vapor deposition equipment, the Al negative electrode of vapour deposition 150 nanometer thickness is made OLED.
Figure BPA00001479921300251
Process is 10 -6Behind the vacuum-sublimation purifying, the every kind of material that is used to make OLED is as electroluminescent material under the holder condition.
[comparative example 1] uses conventional electroluminescent material to make the OLED device
Form after hole injection layer and the hole transmission layer according to the identical method of embodiment 1; Three (oxines) are closed aluminium (III) (Alq) pack in another cell of said vacuum vapor deposition equipment, simultaneously tonka bean camphor 545T (C545T) (its structure is following) is packed in another cell as the electroluminescent substrate material.Two kinds of materials evaporate so that doping to be provided with different speed.Therefore, the thick electroluminescence layer of vapour deposition 30nm on said hole transmission layer.In Alq is benchmark, and doping content is preferably 1-3 weight %.
Figure BPA00001479921300252
According to the method identical with embodiment 1, vapour deposition electron transfer layer and electron injecting layer use another vapor deposition apparatus to deposit the Al negative electrode of 150 nanometer thickness, to make OLED.
[comparative example 2] uses conventional electroluminescent material to make the OLED device
Form after hole injection layer and the hole transmission layer according to the identical method of embodiment 1, pack into another cell of said vacuum vapor deposition equipment of dinaphthyl anthracene (DNA) is interior as the electroluminescent substrate material, simultaneously compound (A) is packed in another cell.Two kinds of materials evaporate with different speed, thereby the doping content of 2-5 weight % is provided, and this doping content is a benchmark in said matrix.Therefore, the thick electroluminescence layer of vapour deposition 30nm on said hole transmission layer.
Figure BPA00001479921300261
According to the method identical with embodiment 1, vapour deposition electron transfer layer and electron injecting layer use another vapor deposition apparatus to deposit the Al negative electrode of 150 nanometer thickness, to make OLED.
In 5000cd/m 2Condition measure the luminous efficiency of the OLED that comprises organic electroluminescent compounds of the present invention (embodiment 1) and conventional electroluminescent compounds (comparative example 1 and 2) respectively, the result is listed in the table 2.
[table 2]
As shown in table 2, when organic electroluminescent compounds of the present invention is used for green electroluminescent equipment, compare the compound of comparative example 1 and 2, obtain having the higher luminous efficiency and the equipment of low-work voltage more, keep similar or higher colour purity simultaneously.

Claims (8)

1. the organic electroluminescent compounds of a chemical formula (1) expression:
Figure FPA00001479921200011
Wherein, L 1And L 2Represent chemical bond independently, be with or without substituent (C6-C30) arylidene, be with or without substituent (C3-C30) inferior heteroaryl; Be with or without substituent 5-to the inferior Heterocyclylalkyl of 7-unit, replace with one or more aromatic ring condensed or unsubstituted 5-to the first inferior Heterocyclylalkyl of 7-, be with or without substituent (C3-C30) cycloalkylidene; With one or more aryl-fused replacements or unsubstituted (C3-C30) cycloalkylidene, be with or without substituent inferior adamantyl, be with or without substituent (C7-C30) inferior bicyclic alkyl; Be with or without substituent (C2-C30) alkenylene; Be with or without substituent (C2-C30) alkynylene, be with or without substituent (C6-C30) aryl (C1-C30) alkylidene group, be with or without substituent (C1-C30) alkylene sulfenyl; Be with or without substituent (C1-C30) alkylene oxide group; Be with or without substituent (C6-C30) inferior aryloxy, be with or without substituent (C6-C30) inferior arylthio ,-O-or-S-;
R 1To R 4And Ar 1Represent hydrogen independently, deuterium, halogen; Be with or without substituent (C1-C30) alkyl, be with or without substituent (C6-C30) aryl, with one or more substituent (C3-C30) Cycloalkylfused replacement or unsubstituted (C6-C30) aryl of being with or without; Be with or without substituent (C3-C30) heteroaryl, be with or without substituent 5-or 7-unit Heterocyclylalkyl, replace with one or more aromatic ring condensed or unsubstituted 5-to the first Heterocyclylalkyl of 7-; Be with or without substituent (C3-C30) naphthenic base; Replace or unsubstituted (C3-C30) naphthenic base with one or more aromatic ring condensed, be with or without substituent adamantyl, be with or without substituent (C7-C30) bicyclic alkyl; Cyanic acid, NR 11R 12, BR 13R 14, PR 15R 16, P (=O) R 17R 18[R wherein 11To R 18Expression is with or without substituent (C1-C30) alkyl independently, is with or without substituent (C6-C30) aryl, or is with or without substituent (C3-C30) heteroaryl]; Be with or without substituent three (C1-C30) alkyl silyl, be with or without substituent two (C1-C30) alkyl (C6-C30) aryl silyl, be with or without substituent three (C6-C30) aryl silyl; Be with or without substituent (C6-C30) aryl (C1-C30) alkyl, be with or without substituent (C1-C30) alkoxyl group, be with or without substituent (C1-C30) alkylthio; Be with or without substituent (C6-C30) aryloxy, be with or without substituent (C6-C30) arylthio, be with or without substituent (C1-C30) alkoxy carbonyl; Be with or without substituent (C1-C30) alkyl-carbonyl, be with or without substituent (C6-C30) aryl carbonyl, be with or without substituent (C2-C30) thiazolinyl; Be with or without substituent (C2-C30) alkynyl, be with or without substituent (C6-C30) aryloxycarbonyl, be with or without substituent (C1-C30) alkoxy-carbonyl oxy; Be with or without substituent (C1-C30) alkyl-carbonyl oxygen base; Be with or without substituent (C6-C30) aryl carbonyl oxygen base, be with or without substituent (C6-C30) aryloxycarbonyl oxygen base, carboxyl; Nitro
Figure FPA00001479921200021
Perhaps hydroxyl, perhaps they separately (C3-30) alkylidene group through being with or without condensed ring or (C3-C30) alkenylene be connected to adjacent substituting group and form alicyclic ring or monocycle or many cyclophanes ring; W representes-(CR 51R 52) m-,-(R 51) C=C (R 52)-,-N (R 53)-,-S-,-O-,-Si (R 54) (R 55)-,-P (R 56)-,-P (=O) (R 57)-,-C (=O)-or-B (R 58)-, and R 51To R 58And R 61To R 63Definition and R 1To R 4Identical;
Each self-contained one or more B that are selected from of said Heterocyclylalkyl and heteroaryl, N, O, S, P (=O), the heteroatoms of Si and P; And
M representes 1 or 2 integer.
2. organic electroluminescent compounds as claimed in claim 1 is characterized in that L 1And L 2, R 1To R 4, R 11To R 18, R 51To R 58, R 61To R 63And Ar 1Each substituting group replace by being selected from following one or more substituting groups independently: hydrogen, deuterium, halogen is with or without (C1-C30) alkyl of halogenic substituent; (C6-C30) aryl is with or without (C3-C30) heteroaryl of (C6-C30) aryl substituent, and 5-is to 7-unit Heterocyclylalkyl, with one or more aromatic ring condensed 5-to the first Heterocyclylalkyl of 7-; (C3-C30) naphthenic base, with one or more aromatic ring condensed (C3-C30) naphthenic base, three (C1-C30) alkyl silyl; Two (C1-C30) alkyl (C6-C30) aryl silyl, three (C6-C30) aryl silyl, adamantyl; (C7-C30) bicyclic alkyl, (C2-C30) thiazolinyl, (C2-C30) alkynyl; Cyanic acid, carbazyl, NR 21R 22, BR 23R 24, PR 25R 26, P (=O) R 27R 28[R wherein 21To R 28Expression is with or without substituent (C1-C30) alkyl independently, is with or without substituent (C6-C30) aryl or is with or without substituent (C3-C30) heteroaryl], (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl; (C1-C30) alkoxyl group, (C1-C30) alkylthio, (C6-C30) aryloxy; (C6-C30) arylthio, (C1-C30) alkoxy carbonyl, (C1-C30) alkyl-carbonyl; (C6-C30) aryl carbonyl, (C6-C30) aryloxycarbonyl, (C1-C30) alkoxy-carbonyl oxy; (C1-C30) alkyl-carbonyl oxygen base, (C6-C30) aryl carbonyl oxygen base, (C6-C30) aryloxycarbonyl oxygen base; Carboxyl, nitro and hydroxyl, perhaps adjacent substituting group is joined together to form ring.
3. organic electroluminescent device, said equipment comprises claim 1 or 2 described organic electroluminescent compounds.
4. organic electroluminescent device as claimed in claim 3, said equipment 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 described one or more organic electroluminescent compounds of claim 1, and one or more doping agents of chemical formula (2) or (3) expression:
Figure FPA00001479921200031
L representes to be with or without substituent (C6-C30) arylidene, is with or without substituent (C3-C30) inferior heteroaryl; R 151To R 154Represent hydrogen independently, deuterium, halogen; Be with or without substituent (C1-C30) alkyl, be with or without substituent (C6-C30) aryl, be with or without substituent (C3-C30) heteroaryl; Be with or without substituent 5-to 7-unit Heterocyclylalkyl, replace with one or more aromatic ring condensed or unsubstituted 5-to the first Heterocyclylalkyl of 7-, be with or without substituent (C3-C30) naphthenic base; Replace or unsubstituted (C3-C30) naphthenic base with one or more aromatic ring condensed, be with or without substituent adamantyl, be with or without substituent (C7-C30) bicyclic alkyl; Cyanic acid, NR 41R 42, BR 43R 44, PR 45R 46, P (=O) R 47R 48[R wherein 41To R 48Expression is with or without substituent (C1-C30) alkyl independently, is with or without substituent (C6-C30) aryl, or is with or without substituent (C3-C30) heteroaryl]; Be with or without substituent three (C1-C30) alkyl silyl, be with or without substituent two (C1-C30) alkyl (C6-C30) aryl silyl, be with or without substituent three (C6-C30) aryl silyl; Be with or without substituent (C6-C30) aryl (C1-C30) alkyl, be with or without substituent (C1-C30) alkoxyl group, be with or without substituent (C1-C30) alkylthio; Be with or without substituent (C6-C30) aryloxy, be with or without substituent (C6-C30) arylthio, be with or without substituent (C1-C30) alkoxy carbonyl; Be with or without substituent (C1-C30) alkyl-carbonyl, be with or without substituent (C6-C30) aryl carbonyl, be with or without substituent (C2-C30) thiazolinyl; Be with or without substituent (C2-C30) alkynyl; Be with or without substituent (C6-C30) aryloxycarbonyl, be with or without substituent (C1-C30) alkoxy-carbonyl oxy, be with or without substituent (C1-C30) alkyl-carbonyl oxygen base; Be with or without substituent (C6-C30) aryl carbonyl oxygen base; Be with or without substituent (C6-C30) aryloxycarbonyl oxygen base, carboxyl, nitro; Or hydroxyl, perhaps they separately (C3-30) alkylidene group through being with or without condensed ring or (C3-C30) alkenylene be connected to adjacent carbons to form condensed ring;
Each self-contained one or more B that are selected from of said Heterocyclylalkyl and heteroaryl, N, O, S, P (=O), the heteroatoms of Si and P.
5. organic electroluminescent device as claimed in claim 4 is characterized in that, said organic layer comprises one or more compounds that are selected from aromatic amine compound and styryl aromatic amine compound.
6. organic electroluminescent device as claimed in claim 4; It is characterized in that said organic layer also comprises one or more metals or its title complex of organo-metallic, period 4 and the period 5 transition metal, lanthanide series metal and the d-transition element that are selected from the 1st family, the 2nd family.
7. organic electroluminescent device as claimed in claim 4 is characterized in that said organic layer comprises electroluminescence layer and charge generation layer.
8. organic electroluminescent device as claimed in claim 4; It is characterized in that; Said organic electroluminescent device is the organic electroluminescent device of emission white light, and said organic layer also comprises the organic electro luminescent layer of one or more layers emission blue light, ruddiness or green glow simultaneously.
CN2010800250539A 2009-03-31 2010-03-24 Novel organic electroluminescent compounds and organic electroluminescent device using the same Pending CN102449110A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
KR1020090027846A KR20100109293A (en) 2009-03-31 2009-03-31 Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR10-2009-0027846 2009-03-31
PCT/KR2010/001813 WO2010114253A2 (en) 2009-03-31 2010-03-24 Novel organic electroluminescent compounds and organic electroluminescent device using the same

Publications (1)

Publication Number Publication Date
CN102449110A true CN102449110A (en) 2012-05-09

Family

ID=42828814

Family Applications (1)

Application Number Title Priority Date Filing Date
CN2010800250539A Pending CN102449110A (en) 2009-03-31 2010-03-24 Novel organic electroluminescent compounds and organic electroluminescent device using the same

Country Status (5)

Country Link
JP (1) JP5781499B2 (en)
KR (1) KR20100109293A (en)
CN (1) CN102449110A (en)
TW (1) TW201105776A (en)
WO (1) WO2010114253A2 (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106831448A (en) * 2016-12-16 2017-06-13 烟台九目化学制品有限公司 A kind of novel aromatic amine luminescent material and its application
CN107954942A (en) * 2017-12-08 2018-04-24 北京鼎材科技有限公司 Benzopyrazines substitutes anthracene derivant and organic electroluminescence device
CN112996779A (en) * 2019-02-20 2021-06-18 株式会社Lg化学 Anthracene derivative and organic electronic device using the same

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5352304B2 (en) * 2008-04-02 2013-11-27 株式会社半導体エネルギー研究所 Anthracene derivative, light emitting material, light emitting element material, coating composition, light emitting element, and light emitting device
EP2112212B1 (en) 2008-04-24 2013-05-29 Semiconductor Energy Laboratory Co., Ltd. Anthracene derivative, light-emitting material, material for light-emitting element, composition for coating light-emitting element, light-emitting device, and electronic device
KR101427605B1 (en) * 2009-03-31 2014-08-07 롬엔드하스전자재료코리아유한회사 Novel organic electroluminescent compounds and organic electroluminescent device using the same
JP5280526B2 (en) 2009-05-29 2013-09-04 出光興産株式会社 Anthracene derivative and organic electroluminescence device using the same
JP5699524B2 (en) * 2010-10-21 2015-04-15 コニカミノルタ株式会社 Organic photoelectric conversion element and solar cell
KR101596547B1 (en) * 2012-02-27 2016-02-23 주식회사 엘지화학 Organic light emitting diode
US9312500B2 (en) 2012-08-31 2016-04-12 Idemitsu Kosan Co., Ltd. Organic electroluminescence device
JP2015233024A (en) * 2012-09-03 2015-12-24 出光興産株式会社 Organic electroluminescent device
US9748492B2 (en) 2012-11-02 2017-08-29 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
KR20150010016A (en) * 2013-07-17 2015-01-28 롬엔드하스전자재료코리아유한회사 Organic electroluminescent device
KR102342399B1 (en) 2013-09-06 2021-12-22 이데미쓰 고산 가부시키가이샤 Anthracene derivative and organic electroluminescent element using same
CN106032350B (en) * 2015-03-09 2019-03-01 广东阿格蕾雅光电材料有限公司 Organic electronic material
CN106033793B (en) * 2015-03-09 2018-11-13 广东阿格蕾雅光电材料有限公司 Organic electroluminescence device
CN106033798B (en) * 2015-03-09 2017-11-14 广东阿格蕾雅光电材料有限公司 Organic electroluminescence device
CN106033801B (en) * 2015-03-09 2018-04-06 广东阿格蕾雅光电材料有限公司 Organic electroluminescence device
KR102601117B1 (en) * 2018-08-17 2023-11-09 주식회사 엘지화학 Novel compound and organic light emitting device comprising the same

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1221434A1 (en) * 2000-08-10 2002-07-10 Mitsui Chemicals, Inc. Hydrocarbon compound, material for organic electroluminescent element and organic electroluminescent element
JP2003229273A (en) * 2002-02-01 2003-08-15 Mitsui Chemicals Inc Organic electric-field light emitting element
WO2003070675A2 (en) * 2002-02-22 2003-08-28 Akzo Nobel N.V. Substituted 10-aryl-11h-benzo[b]fluorenes and 7-aryl-5,6-dihydro-benzo[a]anthracenes for selective effects on estrogen receptors
US20040131880A1 (en) * 2002-12-31 2004-07-08 Eastman Kodak Company Complex fluorene-containing compounds
CN1871323A (en) * 2003-10-24 2006-11-29 伊斯曼柯达公司 Electroluminescent device with anthracene derivative host
WO2007021117A1 (en) * 2005-08-16 2007-02-22 Gracel Display Inc. Green electroluminescent compounds and organic electroluminescent device using the same
WO2008006449A1 (en) * 2006-07-11 2008-01-17 Merck Patent Gmbh Novel materials for organic electroluminescent devices
KR20080031808A (en) * 2006-10-05 2008-04-11 짓쏘 가부시끼가이샤 Benzofluorene compound, emission materials and organic electroluminescent device
US20080160348A1 (en) * 2006-12-29 2008-07-03 Eric Maurice Smith Benzofluorenes for luminescent applications

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101178219B1 (en) * 2008-11-21 2012-08-29 롬엔드하스전자재료코리아유한회사 Electroluminescent device using the electroluminescent compounds
KR101427605B1 (en) * 2009-03-31 2014-08-07 롬엔드하스전자재료코리아유한회사 Novel organic electroluminescent compounds and organic electroluminescent device using the same

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1221434A1 (en) * 2000-08-10 2002-07-10 Mitsui Chemicals, Inc. Hydrocarbon compound, material for organic electroluminescent element and organic electroluminescent element
JP2003229273A (en) * 2002-02-01 2003-08-15 Mitsui Chemicals Inc Organic electric-field light emitting element
WO2003070675A2 (en) * 2002-02-22 2003-08-28 Akzo Nobel N.V. Substituted 10-aryl-11h-benzo[b]fluorenes and 7-aryl-5,6-dihydro-benzo[a]anthracenes for selective effects on estrogen receptors
US20040131880A1 (en) * 2002-12-31 2004-07-08 Eastman Kodak Company Complex fluorene-containing compounds
CN1871323A (en) * 2003-10-24 2006-11-29 伊斯曼柯达公司 Electroluminescent device with anthracene derivative host
WO2007021117A1 (en) * 2005-08-16 2007-02-22 Gracel Display Inc. Green electroluminescent compounds and organic electroluminescent device using the same
WO2008006449A1 (en) * 2006-07-11 2008-01-17 Merck Patent Gmbh Novel materials for organic electroluminescent devices
KR20080031808A (en) * 2006-10-05 2008-04-11 짓쏘 가부시끼가이샤 Benzofluorene compound, emission materials and organic electroluminescent device
US20080160347A1 (en) * 2006-10-05 2008-07-03 Guofang Wang Benzofluorene compound, emission materials and organic electroluminescent device
US20080160348A1 (en) * 2006-12-29 2008-07-03 Eric Maurice Smith Benzofluorenes for luminescent applications

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
郭法文 等: "叠层有机电致发光器件中电荷产生层的优化", 《科技创新导报》, no. 32, 31 December 2007 (2007-12-31), pages 5 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106831448A (en) * 2016-12-16 2017-06-13 烟台九目化学制品有限公司 A kind of novel aromatic amine luminescent material and its application
CN107954942A (en) * 2017-12-08 2018-04-24 北京鼎材科技有限公司 Benzopyrazines substitutes anthracene derivant and organic electroluminescence device
CN107954942B (en) * 2017-12-08 2019-04-09 北京鼎材科技有限公司 Benzopyrazines replaces anthracene derivant and organic electroluminescence device
CN112996779A (en) * 2019-02-20 2021-06-18 株式会社Lg化学 Anthracene derivative and organic electronic device using the same

Also Published As

Publication number Publication date
TW201105776A (en) 2011-02-16
KR20100109293A (en) 2010-10-08
WO2010114253A3 (en) 2010-12-23
JP2012522041A (en) 2012-09-20
JP5781499B2 (en) 2015-09-24
WO2010114253A2 (en) 2010-10-07

Similar Documents

Publication Publication Date Title
CN102449109B (en) The organic electroluminescent device of novel organic electroluminescent compounds and this compound of use
CN102449110A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN102933531B (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN102958906B (en) Novel organic electroluminescent compounds and use the Organnic electroluminescent device of this compound
TWI461507B (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN103249722B (en) For the noval chemical compound of organic electronic material and use the organic electroluminescence device of this compound
TWI457416B (en) Organic electroluminescent element compounds and organic electroluminescent elements
JP5797672B2 (en) Novel organic electroluminescent compound and organic electroluminescent device using the same
CN102803436A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN104193732A (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
CN103189469A (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
CN103298800A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN102083775B (en) Fused polycyclic compound and organic light emitting device having compound
KR20110008784A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20100109050A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20110116635A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN102227486A (en) Organic electroluminscent device using electroluminescent compounds
CN102947294A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20110008892A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN101486900A (en) Novel red electroluminescent compounds and organic electroluminescent device using the same
CN101550085A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20120020901A (en) Novel compounds for organic electronic material and organic electroluminescent device using the same
KR20120044523A (en) Novel organic electroluminescent compounds and organic electroluminescent 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: 20120509