CN102947294B - Novel organic electroluminescent compounds and use the Organnic electroluminescent device of this compound - Google Patents

Novel organic electroluminescent compounds and use the Organnic electroluminescent device of this compound Download PDF

Info

Publication number
CN102947294B
CN102947294B CN201180031487.4A CN201180031487A CN102947294B CN 102947294 B CN102947294 B CN 102947294B CN 201180031487 A CN201180031487 A CN 201180031487A CN 102947294 B CN102947294 B CN 102947294B
Authority
CN
China
Prior art keywords
compound
electroluminescent device
organic
organnic electroluminescent
chemical formula
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.)
Active
Application number
CN201180031487.4A
Other languages
Chinese (zh)
Other versions
CN102947294A (en
Inventor
李秀镛
赵英俊
权赫柱
金圣珉
金奉玉
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
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 CN102947294A publication Critical patent/CN102947294A/en
Application granted granted Critical
Publication of CN102947294B publication Critical patent/CN102947294B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • 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 System
    • 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
    • C07F7/0814—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 is substituted at a C ring atom by Si
    • 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
    • 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 System
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • 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
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
    • 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
    • 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
    • H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
    • 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
    • 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
    • C09K2211/1044—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
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H10K50/155—Hole transporting layers comprising dopants
    • 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]
    • H10K50/17—Carrier injection layers
    • 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]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers

Abstract

The invention provides the organic electroluminescent compounds that chemical formula 1 represents and the Organnic electroluminescent device using this compound.When the substrate material using this organic electroluminescent compounds as the electroluminescent organic material of OLED device, it has good luminous efficiency and elite clone life characteristic.Therefore this compound can be used for manufacturing the OLED device with the very superior operational life-span.

Description

Novel organic electroluminescent compounds and use the Organnic electroluminescent device of this compound
[technical field]
The invention relates to novel organic electroluminescent (electroluminescent) compound and use the Organnic electroluminescent device of this compound.More specifically, be about being used as the novel organic electroluminescent compounds of electroluminescent organic material and using the Organnic electroluminescent device of this compound.
[background technology]
The most important factor of the luminous efficiency of decision organic light emitting diode (OLED) is electroluminescent organic material.Although up to the present fluorescent material has been widely used as electroluminescent organic material uses, because electroluminescent mechanism, research and development phosphor material is one of best approach improving luminous efficiency to original 4 times theoretically.Up to now, iridium (III) complex compound is widely known by the people as phosphor material, it comprises (acac) Ir (btp) 2, Ir (ppy) 3and Firpic, to glow respectively, green glow and blue light.Particularly Japan, Europe and the U.S. carry out research to many phosphor materials recently.
Current CBP the most extensively knows the substrate material as phosphor material.Have been reported the high-level efficiency OLED using and comprise the hole blocking layer of BCP, BAlq etc.BAlq derivative is used to be Pioneer Electronic Corp. (Japan) and other people report as the high-performance OLED of matrix.
Although these materials provide good electroluminescence characters, it still has following shortcoming: during the high-temperature deposition process in vacuum, because the thermostability of low glass transition temperature and difference causes these materials to degrade.Because the power efficiency of OLED represents with (π/voltage) × current efficiency, this power efficiency and voltage are inversely proportional to.Therefore the current consumption reducing OLED needs high power efficiency.In fact, compared to the OLED using fluorescent material, use the OLED of phosphor material to provide more excellent current power (cd/A).But, when being used as matrix (host) of phosphor material with existing material (as BAlq, CBP etc.), because high driving voltage causes the power efficiency using the power efficiency (lumens/watt (lm/W)) of the OLED of phosphor material not significantly to be better than the OLED using fluorescent material.Moreover this OLED device does not have gratifying operation lifetime.Therefore, research and development are more stable and high performance substrate material has its necessity.
[summary of the invention]
Technical problem
By making great efforts in a large number to overcome above-mentioned conventional art problem, present inventor has found novel electroluminescent compounds, and it achieves the Organnic electroluminescent device of the life properties with excellent luminous efficiency and significantly improvement.
An object of the present invention is to provide organic electroluminescent compounds, it has the skeleton providing better luminous efficiency and device lifetime with suitable chromaticity coordinates compared to Traditional dopant agent material, solve foregoing problems simultaneously.Another object of the present invention is to provide a kind of Organnic electroluminescent device with the life properties of high-luminous-efficiency and improvement.
Technical solution
The invention provides the novel organic electroluminescent compounds represented by chemical formula 1 and use the Organnic electroluminescent device of this compound.Because organic electroluminescent compounds of the present invention has good luminous efficiency and excellent lifetime character compared to existing substrate material, therefore it can be used for manufacturing the OLED device with the very superior operational life-span.
Chemical formula 1
Chemical formula 2
Wherein, definition identical with the definition in chemical formula 2,
X represents-O-or-S-; Y represents-S-,-C (R 1) (R 2)-,-Si (R 3) (R 4)-,-N (R 5)-or be selected from the divalent radical of having structure;
Ar 1to Ar 5and R 1to R 5represent hydrogen independently, deuterium, (Cl-C30) alkyl, halogen (Cl-C30) alkyl, halogen, cyano group, (C3-C30) cycloalkyl, 5 to 7 yuan of Heterocyclylalkyls. (C2-C30) thiazolinyl, (C2-C30) alkynyl, (C6-C30) aryl, (Cl-C30) alkoxyl group, (C6-C30) aryloxy, (C3-C30) heteroaryl, (C6-C30) aryl (Cl-C30) alkyl, (C6-C30) arylthio, list or two (Cl-C30) alkylamino radical, list or two (C6-C30) arylamine group, three (Cl-C30) aIkylsilyl groups (tri (Cl-C30) alkylsilyl), two (Cl-C30) alkyl (C6-C30) arylsilyl groups, three (C6-C30) arylsilyl groups, nitro or hydroxyl, or each in them is connected to adjacent substituents to form alicyclic ring by (C3-C30) alkylidene group or (C3-C30) alkenylene key or do not have with condensed ring, the aromatic nucleus of monocycle or many rings, or the hetero-aromatic ring of monocycle or many rings,
Ar 1to Ar 5and R 1to R 5alkyl, cycloalkyl, Heterocyclylalkyl, thiazolinyl, alkynyl, each in aryl and heteroaryl can replace through one or more substituting group further, and described substituting group is selected from deuterium, (Cl-C30) alkyl, halogen (Cl-C30) alkyl, halogen, cyano group, (C3-C30) cycloalkyl, 5 to 7 yuan of Heterocyclylalkyls. (C2-C30) thiazolinyl, (C2-C30) alkynyl, (C6-C30) aryl, (Cl-C30) alkoxyl group, (C6-C30) aryloxy, (C3-C30) heteroaryl, there is (C3-C30) heteroaryl of (Cl-C30) alkyl substituent, there is (C3-C30) heteroaryl of (C6-C30) aryl substituent, (C6-C30) aryl (Cl-C30) alkyl, (C6-C30) arylthio, list or two (Cl-C30) alkylamino radical, list or two (C6-C30) arylamine group, three (Cl-C30) aIkylsilyl groups, two (Cl-C30) alkyl (C6-C30) arylsilyl groups, three (C6-C30) arylsilyl groups, nitro or hydroxyl,
L 1to L 3represent chemical bond independently or be selected from the divalent radical of (C6-C30) arylidene, (C3-C30) inferior heteroaryl, two (Cl-C30) aIkylsilyl groups or two (C6-C30) arylsilyl groups; And
This Heterocyclylalkyl, heteroaryl and hetero-aromatic ring can contain one or more heteroatoms being selected from B, N, O and S.
In the present invention, " alkyl ", " alkoxyl group " and other substituting group containing " alkyl " part comprise straight chain and side chain two kinds.
In the present invention, " aryl " means the organic group of gained after aromatic hydrocarbon removes a hydrogen atom, and can comprise 4 to 7 yuan, and especially the monocycle of 5 or 6 yuan or fused rings, comprise multiple aryl with one or more singly-bound therebetween.The specific examples of this aryl comprises: phenyl, naphthyl, xenyl, anthryl, indenyl, fluorenyl, phenanthryl, benzo phenanthryl (triphenylenyl), pyrenyl, perylene base, base, thick tetraphenyl (naphthacenyl), fluoranthene base (fluoranthenyl) etc., but be not limited to this.This naphthyl comprises 1-naphthyl and 2-naphthyl.And this anthryl comprises 1-anthryl, 2-anthryl and 9-anthryl.And this fluorenyl comprises 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.In the present invention, " heteroaryl " means containing being selected from the heteroatoms of B, N, O and S as 1 to 4 of aromatic nucleus skeletal atom and other residue aromatic nucleus skeletal atom is the aryl of carbon.The polyheteroaromatic that this heteroaryl can be 5 yuan or 6 yuan of bicyclic heteroaryls or obtains with one or more phenyl ring condensation, and can be fractional saturation.This heteroaryl also can comprise the heteroaryl with one or more singly-bound therebetween.
This heteroaryl comprises heteroatoms on wherein ring can through oxidation or quaternary (quaternize) to form the divalent aryl of such as N-oxide compound and quaternary salt.Its specific examples comprises: bicyclic heteroaryl, such as furyl, thienyl, pyrryl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl group, isothiazolyl, different azoles base, azoles base, di azoly, triazinyl, tetrazine base, triazolyl, tetrazyl, furazan base, pyridyl, pyrazinyl, pyrimidyl, pyridazinyl etc.; Polyheteroaromatic, such as benzofuryl, benzothienyl, isobenzofuran-base, benzimidazolyl-, benzothiazolyl, benzisothiazole base, benzisoxa azoles base, benzo azoles base, pseudoindoyl, indyl, indazolyl, diazosulfide base, quinolyl, isoquinolyl, cinnolines base, quinazolyl, quinoxalinyl, carbazyl, coffee pyridine base and benzodioxolyl (benzodioxolyl) etc.; Its N-oxide compound (such as: pyridyl N-oxide and quinoline N-oxide etc.) and quaternary salt etc. thereof, but be not limited to this.
In the present invention, " (C1-C30) alkyl, three (Cl-C30) aIkylsilyl groups, two (Cl-C30) alkyl (C6-C30) arylsilyl groups, (C6-C30) aryl (Cl-C30) alkyl, (Cl-C30) alkoxyl group, (Cl-C30) alkylthio " or the moieties of other resemblance can have 1 to 20 carbon atom, are more specifically l to 10 carbon atom." (C6-C30) aryl, two (Cl-C30) alkyl (C6-C30) arylsilyl groups, three (C6-C30) arylsilyl groups, (C6-C30) aryl (Cl-C30) alkyl, (C6-C30) aryloxy, (C6-C30) arylthio " or the aryl moiety of other resemblance can have 6 to 20 carbon atoms, are more specifically 6 to 12 carbon atoms.The heteroaryl moieties of " (C3-C30) heteroaryl " can have 4 to 20 carbon atoms, is more specifically 4 to 12 carbon atoms.The cycloalkyl moiety of " (C3-C30) cycloalkyl " can have 3 to 20 carbon atoms, is more specifically 3 to 7 carbon atoms.The alkenyl or alkynyl part of " (C2-C30) alkenyl or alkynyl " can have 2 to 20 carbon atoms, is more specifically 2 to 10 carbon atoms.
Chemical formula 1
Be selected from having structure, but be not limited to this.
Wherein,
Y and Ar 1to Ar 3definition identical with the definition in chemical formula 1.
And, the *-L of chemical formula 1 1-L 2-L 3-* is selected from having structure, but is not limited to this:
Organic electroluminescent compounds of the present invention specifically can be listed by following compounds, but the present invention is not limited to following compounds.
The invention provides a kind of Organnic electroluminescent device, it comprises the first electrode: the second electrode; And one or more layers is placed in the organic layer between this first electrode and this second electrode; Wherein this organic layer comprises one or more organic electroluminescent compounds represented by chemical formula 1.
In this Organnic electroluminescent device, when using the organic electroluminescent compounds of one or more chemical formulas l as electroluminescent matrix, this organic layer comprises the electroluminescence layer containing one or more phosphorescent dopants.For the doping agent being applied to Organnic electroluminescent device of the present invention, there is no particular restriction.
In organic electronic device of the present invention, this organic layer, except comprising the organic electroluminescent compounds represented by chemical formula 1, also can comprise the compound that one or more are selected from novel arylamine compound and styryl novel arylamine compound simultaneously further.This novel arylamine compound or styryl novel arylamine compound are illustrated in No. 10-2008-0123276, No. 10-2008-0107606 or 10-2008-0118428 korean patent application case, but are not limited to this.
Moreover, in Organnic electroluminescent device of the present invention, this organic layer, except comprising the organic electroluminescent compounds represented by chemical formula 1, also can comprise one or more further and be selected from the 1st race's organo-metallic, the 2nd race, the transition metal in the 4th cycle and the 5th cycle, the metal of lanthanide series metal and d-transition element or complex compound.This organic layer can comprise electroluminescence layer and charge generation layer.
In addition, this organic layer, except comprising the organic electroluminescent compounds represented by chemical formula 1, also can comprise the organic electro luminescent layer that one or more layers launches blue light, green glow or ruddiness simultaneously simultaneously, to realize the Organnic electroluminescent device of transmitting white.The compound launching blue light, green glow or ruddiness is disclosed in the compound described in No. 10-2008-0123276, No. 10-2008-0107606 or 10-2008-0118428 korean patent application case, but is not limited to this.
In Organnic electroluminescent device of the present invention, the layer that one deck (being called hereinafter " upper layer ") can be selected from chalcogen compound (chalcogenide) layer, metal halide and metal oxide layer is arranged on the internal surface of one or two electrode of this electrode pair.More specifically, metal chalcogenides (the comprising oxide compound) layer of silicon or aluminium can be arranged on the anode surface of this electroluminescent medium (medium) layer, and metal halide or metal oxide layer be arranged on the cathode surface of this electroluminescent medium layer.Operational stability can be obtained whereby.This chalcogen compound can be, such as SiO x(l≤x≤2), AlO x(1≤x≤l.5), SiON, SiAlON etc.This metal halide can be, such as LiF, MgF 2, CaF 2, rare earth metal fluorochemical etc.This metal oxide can be, such as Cs 2o, Li 2o, MgO, SrO, BaO, CaO etc.
In Organnic electroluminescent device of the present invention, be also preferably electric transmission compound and the mixing region of reductibility doping agent or the mixing region of hole transport compound and oxidisability doping agent are arranged at the electrode pair manufactured like this at least one surface on.In this example, because electric transmission compound is reduced into negatively charged ion, electronics is thus made easily to inject from this mixing region and transfer to electroluminescent medium.In addition, because hole transport compound is oxidized to positively charged ion, hole is therefore made easily to inject from its mixing region and transfer to electroluminescent medium.Preferred oxidisability doping agent comprises various Lewis acid and acceptor compound (acceptorcompound).And preferred reductibility doping agent comprises basic metal, alkali metal compound, alkaline-earth metal, rare earth metal, and composition thereof.Moreover the el light emitting device with the transmitting white of two-layer or multilayer electroluminescent layer manufactures as charge generation layer by using reductibility dopant layer.
Advantageous effects
Due to organic electroluminescent compounds of the present invention be used for substrate material as the electroluminescent organic material of OLED device time, have the life characteristic of good luminous efficiency and excellence, therefore it can be used for manufacturing the OLED with the very superior operational life-span.
Embodiment
The present invention further illustrate about organic electroluminescent compounds of the present invention, this compound preparation method and use the luminosity of device of this compound.But following specific examples is only for illustrating, but not intention limits the scope of the invention in any form.
The preparation of [preparation example 1] compound 1
The preparation of compd A
First bromo-for 2,7-bis-9,9-dimethyl fluorenes (150 grams (g), 426 mmoles (mmol)) be dipped in RBF (3 liters (L)) and after replacing with nitrogen, then add THF (2.1L).Treat that this solution is cooled to-78 DEG C, add n-BuLi (170mL, 2.5 volumetric molar concentrations (M) in hexane, 426mmol) stir 1 hour again.Then add trimethyl borate (trimethylborate) (53mL, 469mmol) and stir 12 hours.When completing this reaction with 2MHC1, ethyl acetate (EA)/water is used to extract this mixture.With MgSO 4removal moisture also, after distilling under decompression, is separated (condition is MC: hexane=1:10) by post and obtains compd A (70g, 52%).
The preparation of compd B
By compd A (70,220mmol), 2-iodonitrobenzene (50g, 200mmol), Pd (PPh 3) 4(7g, 6mmol), Na 2cO 3(64g, 600mmol) adds to RBF.Then toluene (1L), EtOH (0.5L) and water (0.3L) are added to this mixture.And stir this reaction mixture 7.5 hours in 90 DEG C.After with the extraction of EA/ water, with MgSO 4remove residual moisture and distill under decompression.Crude compound B (90g) is obtained as the silica filtration of developping agent (developingsolvent) by using methyl chloride (MC).Next step reaction is carried out under not carrying out additional purification.
The preparation of Compound C
Compd B (90g) is dissolved in P (OEt) 3(750mL), 1,2-dichlorobenzene (750mL), and in 150 DEG C stir 9 hours.After removing solvent with distilled water, obtain Compound C (26g, 36%, two step overall yields) by being separated (condition is MC: hexane=1:10) to gained liquid column.
The preparation of Compound D
Cyanuryl chloride (50g, 91mmol) is added in round-bottomed flask (RBF), and be dissolved in THF (1.3L), then be cooled to 0 DEG C.Then phenyl-magnesium-bromide (diethyl ether solution of 225mL, 3M, 675mmol) is slowly dripped in this solution.Stir this reaction soln 3 hours and with EA/H 2o extracts.With MgSO 4remove moisture and after distilling under decompression, obtain crude compound D (37g, 63%) by using MC as the silica filtration of developping agent.Compound D shows its purity and is enough to be used in next step reaction.
The preparation of compd E
At N 2under condition, in RBF, add DMF (40mL) and by NaH(1.9g, 60% is scattered in mineral oil, 50mmol) add RBF and stir.Then the solution of the Compound C (12g, 33mmol) be dissolved in DMF (80mL) is slowly dropped to this suspension.The solution of the Compound D (10.6g, 40mmol) be dissolved in DMF (100mL) after l hour, is more slowly dropped to this mixture by this mixture to be mixed.Stir this reaction mixture 12 hours.When with H 2when O completes this reaction, use EA/H 2o extracts this mixture and distills under decompression.Compd E (12g, 61%) is obtained by carrying out post separation (condition is MC: hexane=1:10).
The preparation of compound 1
By compd E (6g, 10mmol), compound F 17-hydroxy-corticosterone (3.2g, 15.2mmol), Pd (PPh 3) 4(0.58g, 0.5mmol) and K 2cO 3(4.7g, 34mmol) adds RBF.Then by toluene (50mL), EtOH (25mL) and H 20 (17mL) adds to this mixture.In 90 DEG C of stirring these reaction mixtures 12 hours and with EA/H 2o extracts.Treat with MgSO 4remove moisture and after distilling under decompression, obtain compound 1 (4g, 57%) by carrying out post separation (condition is MC: hexane=1:10).
The preparation of [preparation example 2] compound 6
The preparation of compd A
First bromo-for 2,7-bis-9,9-dimethyl fluorenes (150g, 426mmol) to be added in RBF (3L) and to carry out nitrogen replacement.THF (2.1L) is added this solution and cools this solution to-78 DEG C.Add n-BuLi (170mL, 2.5M in hexane, 426mmol) to this solution, then stir this mixture 1 hour.After adding trimethyl borate (53mL, 469mmol), reaction mixture stirs 12 hours.When completing this reaction with 2MHC1, use EA/H 2o extracts this reaction mixture.With MgSO 4removal moisture also, after distilling under decompression, obtains compd A (70g, 52%) by carrying out post separation (condition is MC: hexane=1:10).
The preparation of compd B
By compd A (70g, 220mmol), 2-iodonitrobenzene (50g, 200mmol), Pd (PPh 3) 4(7g, 6mmol), Na 2cO 3(64g, 600mmol) adds in RBF.Then by toluene (1L), EtOH (0.5L) and H 2o (0.3L) adds in this mixture.In 90 DEG C of stirring these reaction mixtures 7.5 hours and with EA/H 2o extracts.With MgSO 4remove moisture and after distilling under decompression, obtain crude compound B (90g) by using MC as the silica filtration of developping agent.Under non-additional purification, carry out the next step.
The preparation of Compound C
Compd B (90g) is dissolved in P (OEt) 3(750mL), 1,2-dichlorobenzene (750mL).Stir this mixture 9 hours in 150 DEG C, and remove solvent with distilled water.Compound C (26g, 36%, two step overall yields) is obtained by carrying out post separation (condition is MC: hexane=l:10) to manufactured red liquid.
The preparation of compound G
By 2,4,6-trichloropyrimidine (16.8g, 91mmol), phenylo boric acid (24.4g, 200mmol), Pd (PPh 3) 4(5.3g, 4.6mmol) and Na 2cO 3(29g, 273mmol) adds in RBF.Then by toluene (350mL), EtOH (100mL) and H 2o (150mL) adds this mixture.In 80 DEG C of stirring these reaction mixtures 3 hours and with EA/H 2o extracts.With MgSO 4removal moisture also, after distilling under decompression, is separated (condition is MC: hexane=1:10) by post and obtains compound G (14g, 58%).
The preparation of compound H
At N 2condition under in RBF, add DMF (40mL) and NaH (1.97g, 60% is scattered in mineral oil, 49.3mmol) added RBF and stirs.Then the solution of the Compound C (11.9g, 32.8mmol) be dissolved in DMF (80mL) is slowly added dropwise to this suspension.Stir this mixture about 1 hour.The solution of the compound G (10.5g, 39.4mmol) be dissolved in DMF (100mL) is slowly added dropwise to this mixture, and stirs this reaction mixture 12 hours.When with H 2when O completes this reaction, use EA/H 2o extracts this mixture and distills under decompression.Be separated (condition is MC: hexane=1:10) by post and obtain compound H (10g, 51%).
The preparation of compound 6
By compound H (5g, 8.4mmol), compound F 17-hydroxy-corticosterone (2.7,13mmol), Pd (PPh 3) 4(0.5g, 0.4mmol) and K 2cO 3(4g, 29mmol) adds RBF.Then by toluene (40mL), EtOH (230mL) and H 2o (14mL) adds wherein.In 90 DEG C of stirring these reaction mixtures 12 hours and with EA/H 2o extracts.Treat with MgSO 4remove moisture and after distilling under decompression, be separated (condition is MC: hexane=1:10) by post and obtain compound 1 (4g, 68%).
The preparation of [preparation example 3] compound 7
The preparation of compd A
First bromo-for 2,7-bis-9,9-methyl fluorenes (150g, 426mmol) to be added in RBF (3L) and after replacing with nitrogen.Again THF (2.1L) is added to this solution, and this solution is cooled to-78 DEG C.After adding n-BuLi (170mL, 2.5M in hexane, 426mmol), then stir this mixture 1 hour.After adding trimethyl borate (53mL, 469mmol), and stir this mixture 12 hours.When completing this reaction with 2MHC1, use EA/H 2o extracts this mixture.With MgSO 4remove moisture and distill under decompression, being separated (condition is MC: hexane=1:10) by post and obtaining compd A (70g, 52%).
The preparation of compd B
By compd A (70g, 220mmol), 2-iodonitrobenzene (50g, 200mmol), Pd (PPh 3) 4(7g, 6mmol), Na 2cO 3(64g, 600mmol) adds in RBF.Then by toluene (1L), EtOH (0.5L) and H 2o (0.3L) adds wherein.In 90 DEG C of stirring these reaction mixtures 7.5 hours and with EA/H 20 extraction.With MgSO 4remove moisture and after distilling under decompression, obtain crude compound B (90g) by using MC as the silica filtration of developping agent.Under non-additional purification, carry out next step reaction.
The preparation of Compound C
Compd B (90g) is dissolved in P (OEt) 3(750mL), 1,2-dichlorobenzene (750mL).Stir this mixture 9 hours in 150 DEG C and remove solvent with distilled water.Compound C (26g, 36%, two step overall yields) is obtained by carrying out post separation (condition is MC: hexane=1:10) to manufactured red liquid.
The preparation of Compound D
Cyanuryl chloride (50g, 91mmol) is added in RBF, and is dissolved in THF (1.3L), then be cooled to 0 DEG C.Then phenyl-magnesium-bromide (diethyl ether solution of 225mL, 3M, 675mmol) is slowly added dropwise to this solution.Stir this reaction soln 3 hours and with EA/H 2o extracts.With MgSO 4remove moisture and after distilling under decompression, obtain crude compound D (37g, 63%) by using MC as the silica filtration of developping agent.Compound D shows its purity and is enough to be used in next step reaction.
The preparation of compd E
At N 2condition under, in RBF, add DMF (40mL) and NaH (1.9g, 60% is scattered in mineral oil, 50mL) add to RBF and stir.Then the solution of the Compound C (12g, 33mmol) be dissolved in DMF (80mL) is slowly dripped in this suspension.The solution of the Compound D (10.6g, 40mmol) be dissolved in DMF (100mL) after 1 hour, more slowly drips in this mixture by this mixture to be mixed.Stir this reaction mixture 12 hours.When with H 2when O completes this reaction, use EA/H 2o extracts this mixture and distills under decompression.Be separated (condition is MC: hexane=1:10) by post and obtain compd E (12g, 61%).
The preparation of compound 7
By compd E (6g, 10mmol), Compound I (3.2g, 15.2mmol), Pd (PPh 3) 4(0.58g, 0.5mmol) and Na 2cO 3(2.1g, 20mmol) adds in RBF.Then by toluene (60mL), EtOH (30mL) and H 2o (10mL) adds wherein.In 90 DEG C of stirring these reaction mixtures 12 hours and with EA/H 2o extracts.Treat with MgSO 4remove moisture and after distilling under decompression, be separated (condition is MC: hexane=1:10) by post and obtain compound 7 (3.4g, 49%).
The preparation of [preparation example 4] compound 8
The preparation of compd A
First bromo-for 2,7-bis-9,9-dimethyl fluorenes (150g, 426mmol) to be immersed in RBF (3L) and to carry out nitrogen replacement, then adding THF (2.1L).This solution to be cooled to-78 DEG C, adds n-BuLi (170mL, 2.5M in hexane, 426mmol), and stirs this mixture 1 hour.Add trimethyl borate (53mL, 469mmol) and stir 12 hours.When completing this reaction with 2MHC1, use ethyl acetate (EA)/H 20 this mixture of extraction.With MgS0 4removal moisture also, after distilling under decompression, obtains compd A (70g, 52%) by carrying out tubing string separation (condition is MC: hexane=1:10) to obtained solid.
The preparation of compd B
By compd A (70g, 220mmol), 2-iodonitrobenzene (50g, 200mmol), Pd (PPh 3) 4(7g, 6mmol) and Na 2cO 3(64g, 600mmol) adds in RBF.Then by toluene (1L), EtOH (0.5L) and H 2o (0.3L) adds wherein.In 90 DEG C of stirring these reaction mixtures 7.5 hours and with EA/H 2o extracts.Remove moisture with MgSO4 and after distilling under decompression, obtain crude compound B (90g) by using MC as the silica filtration of developping agent.Under non-additional purification, carry out next step reaction.
The preparation of Compound C
Compd B (90g) is dissolved in P (OEt) 3(750mL), l, 2-dichlorobenzene (750mL).Stir this mixture 9 hours in 150 DEG C, and remove solvent with distilled water.Compound C (26g, 36%, two step overall yields) is obtained by carrying out post separation (condition is MC: hexane=1:10) to manufactured red liquid.
The preparation of compound G
By 2,4,6-trichloropyrimidine (16.8g, 91mmol), phenylo boric acid (24.4g, 200mmol), Pd (PPh 3) 4(5.3g, 4.6mmol) and Na 2cO 3(29g, 273mmol) adds in RBF.Then by toluene (350mL), EtOH (100mL) and H 2o (150mL) adds this mixture.In 80 DEG C of stirring these reaction mixtures 3 hours and with EA/H 2o extracts.With MgSO 4remove moisture and after distilling under decompression, be separated (condition is MC: hexane=1:10) by post and obtain compound G (14g, 58%).
The preparation of compound H
At N 2condition under, in RBF, add DMF (40mL) and NaH (1.97g, 60% is scattered in mineral oil, 49.3mmol) add RBF and stir.Then the solution of the Compound C (11.9g, 32.8mmol) be dissolved in DMF (80mL) is slowly dripped in this suspension.Stir this mixture about 1 hour.The solution of the compound G (10.5g, 39.4mmol) being dissolved in DMF (100mL) is slowly dripped in this mixture, and stirs this reaction mixture 12 hours.When with H 2when O completes this reaction, use EA/H 2o extracts this mixture and distills under decompression.Be separated (condition is MC: hexane=1:10) by tubing string and obtain compound H (10g, 51%).
The preparation of compound 8
By compound H (5g, 8.4mmol), Compound I (2.7g, 13mmol), Pd (PPh 3) 4(0.5g, 0.4mmol) and Na 2cO 3(1.8g, 17mmol) adds in RBF.Then by toluene (60mL), EtOH (30m) and H 2o (10mL) adds wherein.In 90 DEG C of stirring these reaction mixtures 12 hours and with EA/H 2o extracts.Treat with MgSO 4remove moisture and after distilling under decompression, be separated (condition is MC: hexane=1:10) by post and obtain compound 8 (3.6g, 62%).
Organic electroluminescent compounds has been prepared according to the step of preparation example 1 to 4.Table 1 outlines electroluminescent compounds prepared in this way 1hNMR and MS/FAB data.
Table 1
[embodiment 1] uses the manufacture of the OLED device of organic electroluminescent compounds of the present invention
Electroluminescent organic material of the present invention is used to manufacture OLED device.First, use ultrasonic wave sequentially to be manufactured by OLED(SamsungCorning with trieline, acetone, ethanol and distilled water wash) with the transparency electrode ito thin film (15 Ω/) of glass gained, and be stored in Virahol for subsequent use.
Then, ito substrate is assemblied in the substrate folder of vacuum vapor deposition apparatus, and by 4,4 '; 4 "-three (N, N-(2-naphthyl)-phenyl amido) triphenylamine (2-TNATA) is placed in the cell (cell) of this vacuum vapor deposition apparatus, then this cell taken out 10 -6holder (torr) vacuum.Subsequently, electric current is applied to evaporate 2-TNATA to this cell, and then on this ito substrate, forms the hole injection layer that thickness is 60 nanometers (nm).Then, by N, N '-bis-(Alpha-Naphthyl)-N, N '-phenylbenzene-4,4 '-diamines (NPB) is placed in another cell of this vacuum vapor deposition apparatus; Electric current is applied to evaporate NPB to this cell, and then on this hole injection layer, forms the hole transmission layer that thickness is 20nm.
After forming hole injection layer and hole transmission layer, as following, form electroluminescence layer thereon.Compound 1 is placed in a cell of vacuum vapor deposition apparatus as matrix, and by Ir (ppy) 3[three (2-benzene pyridine) iridium] is placed in another cell as doping agent.Evaporate this bi-material with different rates, and make by being doped in 4 to 10 % by weight the electroluminescence layer that on hole transmission layer, vapour deposition thickness is 30nm.
Subsequently, on electroluminescence layer, vapour deposition thickness is that three (oxine) aluminium (III) (Alq) of 20nm is using as electron transfer layer.Then, treat the oxine lithium (lithiumquinolate of the following structure of tool by vapour deposition thickness being lnm to 2nm, Liq) as after electron injecting layer, another vacuum vapor deposition apparatus is re-used to form the aluminium negative electrode that thickness is 150nm, to produce OLED.
For each compound of OLED all in 10 -6by vacuum sublimation and purifying under torr.Therefore, verified when 6.3 volts (V), had 4.3 milliampere(mA)s/square centimeter (mA/cm 2) current flowing and launch 1310 candela/metre2 (cd/m 2) green glow.
[embodiment 2]
Manufacturing OLED device with the same procedure of embodiment 1, adding compound 6 as except electroluminescence layer substrate material except changing.
Therefore, verified when 6.6V, had 4.3mA/cm 2current flowing and launch the green glow of 1220cd/m2.
[embodiment 3]
Manufacturing OLED device with the same procedure of embodiment 1, adding compound 10 as except the substrate material of electroluminescence layer except changing
Therefore, verified when 6.4V, had 4.1mA/cm 2current flowing and launch 1150cd/m 2green glow.
[comparing embodiment 1] uses the manufacture of the OLED device of conventional organic electro luminescent compounds
With the OLED device that the same procedure of embodiment 1 manufactures, except after forming hole injection layer and hole transmission layer (using the same procedure with embodiment [1]), two (2-methyl-oxine base) (p-phenyl phenol) aluminium (III) (BAlq) is used to substitute organic electroluminescent compounds of the present invention as the electroluminescent substrate material in another cell of this vacuum deposition apparatus.OLED device has been manufactured with the same procedure of embodiment 1, except using 4,4 '-bis-(carbazole-9-base) symbasis (CBP) substitutes compound of the present invention as the substrate material on electroluminescence layer, and uses two (2-methyl-hydroxyl 8-quinolyl) (p-phenyl-phenol) aluminium (III) (BAlq) as hole blocking layer.
Therefore, verified when 7.5V, had 3.9mA/cm 2current flowing and launch 1000cd/m 2green glow.
Organic electroluminescent compounds of the present invention has the character being better than traditional material.In addition, use organic electroluminescent compounds of the present invention to have superior Electroluminescence Properties as the device of substrate material and make driving voltage reduce by 0.9 to 1.2V, thus hoisting power efficiency and improve power loss.

Claims (7)

1. the organic electroluminescent compounds represented by a chemical formula l:
Chemical formula 1
Wherein,
In chemical formula 1 be selected from having structure,
X represents-O-or-S-; Y represents the divalent group being selected from lower group :-S-,-C (R 1) (R 2)-,-Si (R 3) (R 4)-;
Ar 1represent pyridyl, pyrimidyl or triazinyl;
Ar 2to Ar 5represent hydrogen or deuterium independently; R 1to R 4represent (C1-C30) alkyl independently;
Ar 1pyridyl, pyrimidyl and triazinyl one or more substituting groups that can be selected from lower group separately further replace: (C6-C30) aryl;
L 1to L 3represent the *-L in chemical bond or chemical formula 1 independently 1-L 2-L 3-* is selected from having structure:
2. one kind comprises the Organnic electroluminescent device of organic electroluminescent compounds according to claim 1.
3. Organnic electroluminescent device as claimed in claim 2, it comprises the first electrode; Second electrode; And one or more layers is placed in the organic layer between this first electrode and this second electrode: wherein this organic layer comprises one or more organic electroluminescent compounds and one or more phosphorescent dopants.
4. Organnic electroluminescent device as claimed in claim 3, is characterized in that this organic layer comprises the amine compound that one or more are selected from novel arylamine compound and styryl novel arylamine compound further.
5. Organnic electroluminescent device as claimed in claim 3, is characterized in that this organic layer comprises one or more further and is selected from the periodic table of elements the 1st race's organo-metallic, the 2nd race, the transition metal in the 4th cycle and the 5th cycle, the metal of lanthanide series metal and d-transition metal or complex compound.
6. Organnic electroluminescent device as claimed in claim 3, is characterized in that this organic layer comprises electroluminescence layer and charge generation layer.
7. Organnic electroluminescent device as claimed in claim 3, it is the Organnic electroluminescent device of transmitting white, and wherein this organic layer comprises the organic electro luminescent layer that one or more layers launches blue light, ruddiness or green glow further.
CN201180031487.4A 2010-04-30 2011-04-25 Novel organic electroluminescent compounds and use the Organnic electroluminescent device of this compound Active CN102947294B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
KR10-2010-0040384 2010-04-30
KR1020100040384A KR20110120994A (en) 2010-04-30 2010-04-30 Novel organic electroluminescent compounds and organic electroluminescent device using the same
PCT/KR2011/002988 WO2011136520A1 (en) 2010-04-30 2011-04-25 Novel organic electroluminescent compounds and organic electroluminescent device using the same

Publications (2)

Publication Number Publication Date
CN102947294A CN102947294A (en) 2013-02-27
CN102947294B true CN102947294B (en) 2016-03-30

Family

ID=44861730

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201180031487.4A Active CN102947294B (en) 2010-04-30 2011-04-25 Novel organic electroluminescent compounds and use the Organnic electroluminescent device of this compound

Country Status (5)

Country Link
JP (1) JP2013525424A (en)
KR (1) KR20110120994A (en)
CN (1) CN102947294B (en)
TW (1) TW201204810A (en)
WO (1) WO2011136520A1 (en)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20120052879A (en) * 2010-11-16 2012-05-24 롬엔드하스전자재료코리아유한회사 Novel compound for organic electronic material and organic electroluminescent device using the same
US8409729B2 (en) * 2011-07-28 2013-04-02 Universal Display Corporation Host materials for phosphorescent OLEDs
KR20140101661A (en) 2011-11-22 2014-08-20 이데미쓰 고산 가부시키가이샤 Aromatic heterocyclic derivative, material for organic-electroluminescent element, and organic and organic electroluminescent element
WO2013105747A1 (en) * 2012-01-13 2013-07-18 덕산하이메탈(주) Compound for organic electronic element, organic electronic element using same and electronic device thereof
TWI494315B (en) * 2012-02-13 2015-08-01 Duk San Neolux Co Ltd Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
KR20130112342A (en) * 2012-04-03 2013-10-14 롬엔드하스전자재료코리아유한회사 Novel carbazole compounds and organic electroluminescence device containing the same
KR102169443B1 (en) * 2012-04-10 2020-10-23 에스에프씨 주식회사 Heterocyclic com pounds and organic light-emitting diode including the same
KR102191024B1 (en) * 2012-04-10 2020-12-14 에스에프씨 주식회사 Heterocyclic com pounds and organic light-emitting diode including the same
KR102086544B1 (en) 2012-07-31 2020-03-10 삼성디스플레이 주식회사 Condensed compound and organic light emitting diode comprising the same
KR20140032823A (en) * 2012-09-07 2014-03-17 롬엔드하스전자재료코리아유한회사 Organic electroluminescence device
US10227528B2 (en) * 2012-12-21 2019-03-12 Merck Patent Gmbh Materials for organic electroluminescent devices
WO2015170930A1 (en) * 2014-05-08 2015-11-12 Rohm And Haas Electronic Materials Korea Ltd. An electron transport material and an organic electroluminescence device comprising the same
KR101555680B1 (en) * 2015-03-03 2015-09-25 덕산네오룩스 주식회사 Compound for organic electric element, organic electric element comprising the same and electronic device thereof
KR102032267B1 (en) 2016-03-30 2019-11-08 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
WO2017171397A1 (en) * 2016-03-30 2017-10-05 덕산네오룩스 주식회사 Compound for organic electronic element, organic electronic element using same, and electronic device thereof
CN106632413A (en) * 2016-12-30 2017-05-10 上海升翕光电科技有限公司 Benzothiophene carbazole type derivative, preparation method of benzothiophene carbazole type derivative and organic luminous device
CN106632392A (en) * 2016-12-30 2017-05-10 上海升翕光电科技有限公司 Benzothieno carbazole type organic luminescent material, preparation method thereof and organic luminescent device
CN108727424B (en) * 2018-05-15 2020-10-02 北京绿人科技有限责任公司 Organic compound, application thereof and organic electroluminescent device
CN111995564B (en) 2019-12-31 2021-11-12 陕西莱特光电材料股份有限公司 Organic compound, electronic element, and electronic device

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1551694A (en) * 2002-12-24 2004-12-01 ����Sdi��ʽ���� Blue light-emitting polymer and organic el element using the same
CN1749295A (en) * 2004-09-18 2006-03-22 三星Sdi株式会社 Blue luminescent polymer and organoelectroluminescent device using the same
EP1727396A1 (en) * 2004-03-19 2006-11-29 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
US20090302743A1 (en) * 2008-06-05 2009-12-10 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same
US20090309488A1 (en) * 2008-06-05 2009-12-17 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105037368B (en) * 2008-06-05 2017-08-29 出光兴产株式会社 Halogen compound, polycyclic compound, and organic electroluminescent element using same
JP5666907B2 (en) * 2008-06-05 2015-02-12 出光興産株式会社 Halogen compound, polycyclic compound, and organic electroluminescence device using the same
JP5493309B2 (en) * 2008-08-18 2014-05-14 コニカミノルタ株式会社 ORGANIC ELECTROLUMINESCENT ELEMENT MATERIAL, ORGANIC ELECTROLUMINESCENT ELEMENT, DISPLAY DEVICE AND LIGHTING DEVICE

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1551694A (en) * 2002-12-24 2004-12-01 ����Sdi��ʽ���� Blue light-emitting polymer and organic el element using the same
EP1727396A1 (en) * 2004-03-19 2006-11-29 Idemitsu Kosan Co., Ltd. Organic electroluminescent device
CN1749295A (en) * 2004-09-18 2006-03-22 三星Sdi株式会社 Blue luminescent polymer and organoelectroluminescent device using the same
US20090302743A1 (en) * 2008-06-05 2009-12-10 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same
US20090309488A1 (en) * 2008-06-05 2009-12-17 Idemitsu Kosan Co., Ltd. Material for organic electroluminescence device and organic electroluminescence device using the same

Also Published As

Publication number Publication date
CN102947294A (en) 2013-02-27
KR20110120994A (en) 2011-11-07
WO2011136520A1 (en) 2011-11-03
TW201204810A (en) 2012-02-01
JP2013525424A (en) 2013-06-20

Similar Documents

Publication Publication Date Title
CN102947294B (en) Novel organic electroluminescent compounds and use the Organnic electroluminescent device of this compound
CN102958906B (en) Novel organic electroluminescent compounds and use the Organnic electroluminescent device of this compound
JP6535671B2 (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
CN102933531B (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR102128702B1 (en) Novel organic electroluminescence compounds and organic electroluminescence device containing the same
CN104080882B (en) The organic electroluminescence device of organic electroluminescent compounds and this compound of use
CN103384712B (en) The organic electroluminescence device of new organic electroluminescent compounds and this compound of use
JP6478978B2 (en) Organic electroluminescent compound and organic electroluminescent device comprising the same
CN103249800A (en) Novel compounds for organic electronic material and organic electroluminescent device using the same
CN104193732A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
CN103534251A (en) Novel compounds for organic electronic material and organic electroluminescent device using the same
CN103249722A (en) Novel compounds for organic electronic material and organic electroluminescent device using the same
CN104271582A (en) Novel organic electroluminescence compounds and organic electroluminescence device containing the same
CN106604923A (en) Organic electroluminescent compounds and organic electroluminescent devices comprising the same
KR20110049217A (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
KR20110066494A (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
KR20120122812A (en) Novel organic electroluminescence compounds and organic electroluminescence device using the same
KR20120032054A (en) Novel organic luminescent compounds and organic electroluminescent device using the same
CN104066739A (en) Novel organic electroluminescent compounds and organic electroluminescent device using the same
KR20110093055A (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
CN104854089A (en) Organic electroluminescence compounds and organic electroluminescence device comprising the same
CN103228661A (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
C14 Grant of patent or utility model
GR01 Patent grant