CN110268036A - Organic illuminating element - Google Patents
Organic illuminating element Download PDFInfo
- Publication number
- CN110268036A CN110268036A CN201880010433.1A CN201880010433A CN110268036A CN 110268036 A CN110268036 A CN 110268036A CN 201880010433 A CN201880010433 A CN 201880010433A CN 110268036 A CN110268036 A CN 110268036A
- Authority
- CN
- China
- Prior art keywords
- chemical formula
- unsubstituted
- illuminating element
- substituted
- organic illuminating
- 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.)
- Granted
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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—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]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms 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
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
- C09K2211/1062—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with oxygen
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The present invention provides organic illuminating element.
Description
Technical field
With the mutual reference of related application
This application claims South Korea patent application the 10-2017-0089708th priority based on July 14th, 2017,
Full content as part of this specification disclosed in document comprising the South Korea patent application.
The present invention relates to organic illuminating elements.
Background technique
Under normal conditions, organic light emission phenomenon refers to the phenomenon that making electric energy be converted to luminous energy using organic substance.Using having
The organic illuminating element of machine luminescence phenomenon has wide viewing angle, excellent contrast, quick response time, and brightness, driving
Voltage and response speed excellent, to largely be studied.
Organic illuminating element usually has the organic matter comprising anode and cathode and between above-mentioned anode and cathode
The structure of layer.In order to improve the efficiency and stability of organic illuminating element, above-mentioned organic matter layer is in most cases by being utilized respectively
The multilayered structure that different substances is constituted is formed, for example, can be by hole injection layer, hole transmission layer, luminescent layer, electron-transport
The formation such as layer, electron injecting layer.For the structure of such organic illuminating element, if applying electricity between electrodes
Pressure, then hole is injected into organic matter layer from anode, and electronics is injected into organic matter layer from cathode, when institute's injected holes and electronics phase
It will form exciton (exciton) when chance, and light will be issued when the exciton transits to ground state again.
It is lasting to require to develop new material for the organic matter for organic illuminating element as described above.
Existing technical literature
Patent document
(patent document 1) Korean Patent Publication No. the 10-2000-0051826th
Summary of the invention
Want the project solved
The present invention provides organic illuminating element.
The solution of project
The present invention a kind of organic illuminating element is provided comprising: anode, it is opposed with above-mentioned anode and have cathode,
And having one layer or more of organic matter layer between above-mentioned anode and cathode, organic matter layer includes luminescent layer, above-mentioned to shine
Layer includes the compound indicated by following chemical formula 1, includes the change indicated by following chemical formula 2 between above-mentioned anode and luminescent layer
Close object.
[chemical formula 1]
In above-mentioned chemical formula 1,
L1For singly-bound or substituted or unsubstituted C6-60Arlydene,
L2For singly-bound, substituted or unsubstituted C6-60Arlydene or substituted or unsubstituted 1 comprising in O, N, Si and S
A above C2-60Inferior heteroaryl,
Y1To Y3It is each independently N or C-R1, and at least any one is N, R1For hydrogen or substituted or unsubstituted C1-40
Alkyl,
Ar1And Ar2It is each independently substituted or unsubstituted C6-60Aryl or it is substituted or unsubstituted comprising O, N,
1 or more C in Si and S2-60Heteroaryl,
Ar3For substituted or unsubstituted C6-60Aryl,
The integer that m is 1 to 2,
[chemical formula 2]
In above-mentioned chemical formula 2,
Ar4And Ar5It is each independently substituted or unsubstituted C6-60Aryl,
R1And R2It is each independently substituted or unsubstituted C6-20Aryl,
N1 and n2 is each independently 0 or 1.
Invention effect
The present invention uses material of main part of the compound indicated by above-mentioned chemical formula 1 as luminescent layer, using by above-mentioned
Material of the compound as the organic matter layer between anode and luminescent layer that indicates of chemical formula 2, can be real so as to provide
Existing low voltage drive and the organic illuminating element for showing high efficiency and long-life characteristics.
Detailed description of the invention
Fig. 1 illustrates by substrate 1, anode 2, hole injection layer 3, hole transmission layer 5, electronic barrier layer 6, luminescent layer 7, electricity
The example for the organic illuminating element that sub- transport layer 8 and cathode 4 are constituted.
Specific embodiment
In the following, being illustrated in more details to help to understand the present invention.
The present invention provides a kind of organic illuminating element, wherein and luminescent layer includes the compound indicated by above-mentioned chemical formula 1,
Compound between anode and luminescent layer comprising being indicated by above-mentioned chemical formula 2.
In this specification,Indicate that the key connecting with other compounds, singly-bound refer to by L1Or L2It does not deposit the part of expression
Other atoms the case where.For example, working as the L of chemical formula 11For singly-bound, Y1To Y3When for N, by Ar1And Ar2Substituted triazine replaces
Base can directly be connect with dibenzofurans.
In this specification, " substituted or unsubstituted " this term can refer to by RaIt is substituted or unsubstituted, RaCan be
Deuterium；Halogen group；Cyano；Nitro；Amino；The alkyl of carbon atom number 1 to 40；The halogenated alkyl of carbon atom number 1 to 40；Replace or
The unsubstituted miscellaneous alkyl comprising the more than one carbon atom number 1 to 40 in O, N, Si and S；It is substituted or unsubstituted comprising O,
N, the miscellaneous halogenated alkyl of the more than one carbon atom number 1 to 40 in Si and S；Or the alkenyl of carbon atom number 2 to 40.
In this specification, halogen group can be fluorine, chlorine, bromine or iodine.
In this specification, the alkyl of carbon atom number 1 to 40 can be straight chain, branch or cyclic alkyl.Specifically, carbon is former
The alkyl that subnumber is 1 to 40 can be the straight chained alkyl of carbon atom number 1 to 40, the straight chained alkyl of carbon atom number 1 to 20, carbon atom
The branch or cyclic annular alkane of the straight chained alkyl of number 1 to 10, the branch of carbon atom number 3 to 40 or cyclic alkyl, carbon atom number 3 to 20
The branch or cyclic alkyl of base or carbon atom number 3 to 10.More specifically, the alkyl of carbon atom number 1 to 40 can be first
Base, ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group, tert-butyl, n-pentyl, isopentyl, neopentyl or cyclohexyl etc..But
It's not limited to that.
In this specification, in the miscellaneous alkyl of carbon atom number 1 to 40, the more than one carbon atom of alkyl can be respectively independent
Ground is replaced by O, N, Si or S.For example, the example as straight chained alkyl, the miscellaneous alkyl that No. 1 carbon of normal-butyl is replaced by O is positive third
Oxygroup, the miscellaneous alkyl replaced by N are positive the third amino, and the miscellaneous alkyl replaced by Si is positive propylsilyl, the miscellaneous alkane replaced by S
Base is positive rosickyite base.Also, as the example of branched alkyl, the miscellaneous alkyl that No. 1 carbon of neopentyl is replaced by O is tert-butoxy,
The miscellaneous alkyl replaced by N is tertiary fourth amino, and the miscellaneous alkyl replaced by Si is tert. butylsilyl-group, and the miscellaneous alkyl replaced by S is
Tertiary butylthio.In addition, the example as cyclic alkyl, the miscellaneous alkyl that No. 2 carbon of cyclohexyl are replaced by O is 2- THP trtrahydropyranyl
(2-tetrahydropyranyl), the miscellaneous alkyl replaced by N are 2- piperidyl, and the miscellaneous alkyl replaced by Si is 1- sila-hexamethylene
Base (1-sila-cyclohexyl), the miscellaneous alkyl replaced by S are 2- tetrahydro thiapyran base (2-tetrahydrothiopyranyl).
Specifically, the miscellaneous alkyl of carbon atom number 1 to 40 can be the straight chain of carbon atom number 1 to 40, branch or cyclic annular hydroxyalkyl；Carbon
Straight chain, branch or the cyclic alkoxy of atomicity 1 to 40；Straight chain, branch or the cyclic alkoxy alkane of carbon atom number 2 to 40
Base；Straight chain, branch or the cyclic aminoalkyl of carbon atom number 1 to 40；Straight chain, branch or the cyclic annular alkane of carbon atom number 1 to 40
Base amino；Straight chain, branch or the cyclic alkylamido alkyl of carbon atom number 1 to 40；The straight chain of carbon atom number 1 to 40, branch,
Or cyclic annular silicyl alkane (oxygen) base；Straight chain, branch or cyclic annular alkane (oxygen) base silicyl of carbon atom number 1 to 40；Carbon atom
Straight chain, branch or cyclic annular alkane (oxygen) base silicyl alkane (oxygen) base of number 1 to 40；The straight chain of carbon atom number 1 to 40, branch or
Cyclic annular mercaptoalkyl；Straight chain, branch or the cyclic alkylthio of carbon atom number 1 to 40；Or straight chain, the branch of carbon atom number 2 to 40
Chain or cyclic alkylthio alkyl.More specifically, the miscellaneous alkyl of carbon atom number 1 to 40 can enumerate methylol, methoxyl group, ethoxy
Base, positive propoxy, isopropoxy, tert-butoxy, cyclohexyloxy, methoxy, i-propoxymethyl, cyclohexyloxy methyl,
2- THP trtrahydropyranyl (2-tetrahydropyranyl), amino methyl, methylamino, n-propylamine base, tertiary fourth amino, methyl ammonia
Base propyl, 2- piperidyl, n-propyl silicyl, trimethyl silyl, dimethylmethoxysilylgroups groups, tert-butyl first silicon
Alkyl, 1- sila-cyclohexyl (1-sila-cyclohexyl), positive rosickyite base, tertiary butylthio or 2- tetrahydro thiapyran base (2-
Tetrahydrothiopyranyl) etc..But not limited to this.
In this specification, the alkenyl of carbon atom number 2 to 40 can be straight chain, branch or cyclic alkenyl radical.Specifically, carbon
The alkenyl of atomicity 2 to 40 can be the straight-chain alkenyl of carbon atom number 2 to 40；The straight-chain alkenyl of carbon atom number 2 to 20；Carbon atom
The straight-chain alkenyl of number 2 to 10；The branched-chain alkenyl of carbon atom number 3 to 40；The branched-chain alkenyl of carbon atom number 3 to 20；Carbon atom number 3 to
10 branched-chain alkenyl；The cyclic alkenyl radical of carbon atom number 5 to 40；The cyclic alkenyl radical of carbon atom number 5 to 20；Or carbon atom number 5 to
10 cyclic alkenyl radical.More specifically, the alkenyl of carbon atom number 2 to 40 can for vinyl, acrylic, cyclobutenyl, pentenyl,
Or cyclohexenyl group etc..But not limited to this.
In this specification, the aryl of carbon atom number 6 to 60 can be monocyclic aryl or polyaromatic.Specifically, carbon is former
The aryl of subnumber 6 to 60 can be the monocycle or polyaromatic of carbon atom number 6 to 30；Or carbon atom number 6 to 20 monocycle or
Polyaromatic.More specifically, for the aryl of carbon atom number 6 to 60, as monocyclic aryl, can for phenyl, xenyl,
Or terphenyl etc., as polyaromatic, can for naphthalene, anthryl, aphthacene base, phenanthryl, triphenylene, fluoranthene base, pyrenyl,
Base,Base or fluorenyl.
In addition, the aryl of carbon atom number 6 to 60 can have more than two phases in monocyclic aryl and polyaromatic
The structure to connect.Specifically, the aryl of carbon atom number 6 to 60 can have on polyaromatic connect polyaromatic and/
Or the structure of monocyclic aryl.More specifically, the aryl of carbon atom number 6 to 60 can be naphthylphenyl, anthryl phenyl, phenanthryl benzene
Base, triphenylene phenyl, pyrenyl phenyl, base phenyl,Base phenyl, fluorenyl phenyl, phenyl napthyl, phenyl anthryl, phenyl three
Xenyl or phenyl napthyl phenyl etc..But not limited to this.
In this specification, fluorenyl can be substituted, and two substituent groups can be bonded to each other and form spiro structure.Above-mentioned fluorenyl
In substituted situation, Ke Yiwei
Deng.But not limited to this.
In this specification, in the heteroaryl of carbon atom number 2 to 60,1 or more carbon atom of aryl can be respectively independent
Ground is replaced by O, N, Si or S.For example, the heteroaryl that No. 9 carbon of fluorenyl are replaced by O is dibenzofuran group, the heteroaryl replaced by N
Base is carbazyl, and the heteroaryl replaced by Si is 9- sila-fluorenyl, and the heteroaryl replaced by S is dibenzothiophene.It is specific and
Speech, the heteroaryl of carbon atom number 2 to 60 can be the heteroaryl of carbon atom number 2 to 30；Or the heteroaryl that carbon atom number is 2 to 20
Base.More specifically, the heteroaryl of carbon atom number 2 to 60 can for thienyl, furyl, pyrrole radicals, imidazole radicals, thiazolyl,Oxazolyl,Di azoly, triazolyl, pyridyl group, bipyridyl, pyrimidine radicals, triazine radical, triazolyl, acridinyl, pyridazine group,
Pyrazinyl, quinolyl, quinazolyl, quinoxalinyl, phthalazinyl, Pyridopyrimidine base, pyridine pyrazinyl, pyrazine and pyrazinyl,
Isoquinolyl, indyl, carbazyl, benzoOxazolyl, benzimidazolyl, benzothiazolyl, benzo carbazole base, benzothiophene
It is base, dibenzothiophene, benzofuranyl, phenanthroline (phenanthroline), thiazolyl, differentOxazolyl,Diazole
Base, thiadiazolyl group, benzothiazolyl, phenothiazinyl and dibenzofuran group etc., it is not limited to this.
In this specification, arlydene refers to the divalent organic group that any one hydroperoxyl radical of above-mentioned aryl is removed, sub-
Heteroaryl refers to the divalent organic group that any one hydroperoxyl radical of above-mentioned heteroaryl is removed.
In above-mentioned chemical formula 1, L1It can be able to be more specifically singly-bound for singly-bound or phenylene.
In above-mentioned chemical formula 1, Y1To Y3It can be each independently N or C-H, and at least any one is N.
In above-mentioned chemical formula 1, Ar1And Ar2Can be each independently from selected from benzene, biphenyl, terphenyl, naphthalene, phenanthrene,
Triphenylene, 9,9- dimethyl fluorene, 9,9- diphenylfluorene, spiral shell [fluorenes -9,9'- fluorenes], dibenzofurans, dibenzothiophenes, N- phenyl
Carbazole, phenyl -9,9- dimethyl fluorene, 1 valence of phenyl dibenzofurans and aromatic hydrocarbons or heteroaryl hydrocarbon in phenyl dibenzothiophenes are residual
Base.
Specifically, Ar1And Ar21 from the aromatic hydrocarbons in benzene, biphenyl and terphenyl can be each independently
Valence residue.
More specifically, Ar1And Ar2Phenyl or xenyl can be each independently.
In above-mentioned chemical formula 1, L2It can be for singly-bound or from selected from benzene, naphthalene, 9,9- dimethyl fluorene, 9,9- diphenyl
Fluorenes, spiral shell [fluorenes -9,9'- fluorenes], dibenzofurans, dibenzothiophenes, benzothiophene simultaneously [2,3-d] pyrimidine (benzothieno [2,
3-d] pyrimidene) and the benzothiophene simultaneously aromatic hydrocarbons in [3,2-d] pyrimidine (benzothieno [3,2-d] pyrimidene)
Or the divalent residue of heteroaryl hydrocarbon.
In above-mentioned chemical formula 1, Ar3Can for from selected from benzene, biphenyl, terphenyl, naphthalene, anthracene, aphthacene,
(chrysene), 1 valence of phenanthrene, triphenylene, fluoranthene (Fluoranthene), pyrene (pyrene) and the aromatic hydrocarbons in (perylene)
Residue.
In above-mentioned chemical formula 1, L2-Ar3It can be the substituent group in following substituent groups.
The compound indicated by above-mentioned chemical formula 1 can be in the compound indicated by following chemical formula 1-1 and 1-2
Compound.
[chemical formula 1-1]
In above-mentioned chemical formula 1-1,
L1、Y1To Y3、Ar1And Ar2It is identical as chemical formula 1,
L2aFor singly-bound, substituted or unsubstituted C6-60Arlydene or substituted or unsubstituted comprising in O, N, Si and S
1 or more C2-60Inferior heteroaryl,
Ar3aFor substituted or unsubstituted C6-60Aryl,
[chemical formula 1-2]
In above-mentioned chemical formula 1-2,
L1、Y1To Y3、Ar1And Ar2It is identical as chemical formula 1,
L2bAnd L2cIt is each independently singly-bound, substituted or unsubstituted C6-60Arlydene or substituted or unsubstituted packet
Containing 1 or more C in O, N, Si and S2-60Inferior heteroaryl,
Ar3bAnd Ar3cIt is each independently substituted or unsubstituted C6-60Aryl,
The L of above-mentioned chemical formula 1-1 and 1-21、Y1To Y3、Ar1And Ar2With the L of chemical formula 11、Y1To Y3、Ar1And Ar2It is identical,
L2aTo L2cWith the L of chemical formula 12It is corresponding, Ar3aTo Ar3cWith chemical formula 1 and Ar3It is corresponding, L1And L2、Y1To Y3、Ar1To Ar3
Concrete example explain in detail in front, therefore detailed explanation is omitted here.
The compound indicated by above-mentioned chemical formula 1 can be selected from following compounds.
In above-mentioned chemical formula 2, Ar4And Ar5Can be each independently from selected from benzene, biphenyl, terphenyl, naphthalene, phenanthrene,
In triphenylene, phenyl terphenyl, phenylnaphthalene, phenyl phenanthrene, 9,9- dimethyl fluorene, 9,9- diphenylfluorene and spiral shell [fluorenes -9,9'- fluorenes]
1 valence residue of aromatic hydrocarbons.
Specifically, Ar4And Ar5It can be each independently from selected from benzene, biphenyl, terphenyl, triphenylene, phenyl
1 valence residue of terphenyl, phenylnaphthalene and the aromatic hydrocarbons in phenyl phenanthrene.
In above-mentioned chemical formula 2, R1And R2For phenyl, n1 and n2 can be each independently 0 or 1.Above-mentioned n1 or n2 is
Refer to the carbazyl of above-mentioned chemical formula 2 not by R1Or R2Replace.
The compound indicated by above-mentioned chemical formula 2 can be selected from following compounds.
Organic illuminating element of the invention includes anode, and the cathode that has opposed with above-mentioned anode and is had upper
State one layer or more of organic matter layer between anode and cathode.Above-mentioned organic matter layer is by being laminated with two layers or more of organic matter layer
Multilayered structure is formed.Specifically, above-mentioned organic matter layer may include the hole injection layer adjacent with anode, have in above-mentioned sky
Hole transmission layer on the implanted layer of cave has the electronic barrier layer on above-mentioned hole transmission layer and has in above-mentioned electronics
Luminescent layer on barrier layer.In addition, above-mentioned organic illuminating element can include electron-transport between above-mentioned luminescent layer and cathode
Layer and electron injecting layer etc..But it's not limited to that for the structure of organic illuminating element, may include more a small number of organic matters
Layer.
Organic illuminating element according to the present invention can be the organic matter that anode, one layer or more are sequentially laminated on substrate
The organic illuminating element of the structure (standard type (normal type)) of layer and cathode.In addition, organic light emission member according to the present invention
Part can be the reverse structure (inversion type that cathode, one layer or more of organic matter layer and anode are sequentially laminated on substrate
(inverted type)) organic illuminating element.For example, the structure of the organic illuminating element of an embodiment according to the present invention
It is illustrated in Fig. 1.
Fig. 1 illustrates by substrate 1, anode 2, hole injection layer 3, hole transmission layer 5, electronic barrier layer 6, luminescent layer 7, electricity
The example for the organic illuminating element that sub- transport layer 8 and cathode 4 are constituted.In structure as described above, indicated by above-mentioned chemical formula 1
Compound be included in luminescent layer 7, the compound indicated by above-mentioned chemical formula 2 is included in hole injection layer 3, hole transmission layer
5 and electron injecting layer 6 in one layer or more of organic matter layer in, so as to reduce the driving voltage of organic illuminating element, mention
High efficiency and service life.
Organic illuminating element according to the present invention includes the compound indicated by above-mentioned chemical formula 1 in above-mentioned luminescent layer,
Comprising by above-mentioned chemistry in more than one organic matter layer in above-mentioned hole injection layer, hole transmission layer and electronic barrier layer
The compound that formula 2 indicates, in addition to this, well known material and the method in the technical field of can use are manufactured.On in addition,
Stating multiple organic matter layers can be formed by identical substance or different substances.
For example, organic illuminating element according to the present invention can be by stacking gradually appointing in anode and cathode on substrate
Another electrode in one electrode, organic matter layer and above-mentioned anode and cathode and manufacture.At this moment, it can manufacture as follows: benefit
With the PVD (Physical of sputtering method (sputtering) or electron beam evaporation method (e-beam evaporation) etc
Vapor Deposition, physical vapour deposition (PVD)) method, on substrate evaporation metal or conductive metal oxide or
Their alloy and form anode, then on the anode formed include hole injection layer, hole transmission layer, luminescent layer and electronics
After the organic matter layer of transport layer, vapor deposition can be used as the substance of cathode and manufacture on the organic matter layer.Other than this method,
Can also on substrate successively evaporation cathode substance, organic matter layer, anode material and manufacture organic illuminating element (WO 2003/
012890).But it's not limited to that for manufacturing method.
In addition, being manufactured about the compound indicated by above-mentioned chemical formula 1 and the compound indicated by above-mentioned chemical formula 2
When organic illuminating element, vacuum vapour deposition not only can use, can also form organic matter layer using solution coating method.At this
In, so-called solution coating method refers to, spin-coating method, dip coating, knife coating, ink jet printing method, silk screen print method, spray-on process, roller coating
Method etc., it is not limited to this.
As above-mentioned anode material, generally for enabling hole successfully to inject to organic matter layer, preferably work function
Big substance.As the concrete example of above-mentioned anode material, there are the metals such as vanadium, chromium, copper, zinc, gold or their alloy；Zinc oxide,
The metal oxides such as indium oxide, tin indium oxide (ITO), indium zinc oxide (IZO)；ZnO:Al or SNO2: the metals such as Sb and oxide
Combination；Poly- (3 methyl thiophene), poly- [3,4- (ethylidene -1,2- dioxy) thiophene] (PEDOT), polypyrrole and polyaniline etc. are led
Electrical macromolecule etc., it is not limited to this.
As above-mentioned cathode substance, generally for electronics is injected easily to organic matter layer, preferably work function is small
Substance.As the concrete example of cathode substance, have the metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminium, silver, tin and lead or it
Alloy；LiF/Al or LiO2Multilayered structures substance such as/Al etc., it is not limited to this.
Above-mentioned hole injection layer is the layer in the hole that injection carrys out self-electrode, as hole injecting material, preferably followingization
Close object: the ability with transporting holes has hole injection effect from anode, for the excellent of luminescent layer or luminescent material
Hole inject effect, prevent in luminescent layer generated exciton to migrate to electron injecting layer or electron injection material, and thin
Film Forming ability is excellent.As hole injecting material, the compound indicated by above-mentioned chemical formula 2 or existing conduct can be used
Hole injecting material and known compound.It is preferred that HOMO (highest occupied molecular orbital(HOMO), the highest of hole injecting material
Occupied molecular orbital) between the work function of anode material and the HOMO of surrounding organic matter layer.As
The concrete example of hole injecting material has metalloporphyrin (porphyrin), Oligopoly thiophene, aryl amine system organic matter, six nitriles, six azepine
It is organic matter, anthraquinone and polyphenyl that benzophenanthrene system organic matter, quinacridone (quinacridone), which are organic matter, (perylene),
Amine and polythiophene system electroconductive polymer etc., it is not limited to this.
Above-mentioned hole transmission layer is to receive the hole from hole injection layer and by the layer of hole transport to luminescent layer, as
The material for forming hole transmission layer, can be used the compound indicated by above-mentioned chemical formula 2.For being indicated by above-mentioned chemical formula 2
Compound, explain in detail in front, therefore detailed explanation is omitted here.
Since the hole mobility of the compound indicated by above-mentioned chemical formula 2 is big, it is suitble to receive from anode or sky
The hole of cave implanted layer simultaneously transfers them to luminescent layer.
On the other hand, if hole injection layer or electronic barrier layer are that the compound indicated by above-mentioned chemical formula 2 is formed,
Then above-mentioned hole transmission layer can be formed by well known hole transporting material in the technical field of the invention.As such sky
The concrete example of cave transport materials has aryl amine system organic matter, electroconductive polymer and exists simultaneously conjugate moiety and non-conjugated
Partial block copolymer etc., it is not limited to this.
Electronic barrier layer can be formed between above-mentioned hole transmission layer and luminescent layer, so that being passed to the electricity of luminescent layer
Son can not be mobile to anode side.As such material for forming electronic barrier layer, can be used is indicated by above-mentioned chemical formula 2
Compound.In particular, can then be significantly improved when using electronic barrier layer is formed by the compound that above-mentioned chemical formula 2 indicates
The efficiency of organic illuminating element.
Above-mentioned luminescent layer is can to receive respectively hole and electronics from hole transmission layer and electron transfer layer and tie them
The layer of the light of visible light region is closed and issues, this luminescent layer may include material of main part and dopant material.
As aforementioned body material, the compound indicated by above-mentioned chemical formula 1 can be used.For by above-mentioned chemical formula 1
The compound of expression, explains in detail in front, therefore detailed explanation is omitted here.
In addition, the compound indicated by above-mentioned chemical formula 1 can be used and by following chemical formula as aforementioned body material
3 compounds indicated.
[chemical formula 3]
In above-mentioned chemical formula 3,
Ar7And Ar8It is each independently substituted or unsubstituted C6-60Aryl.
In above-mentioned chemical formula 3, Ar7And Ar8Can be each independently from selected from benzene, biphenyl, terphenyl, naphthalene, phenanthrene,
In triphenylene, 9,9- dimethyl fluorene, 9,9- diphenylfluorene, spiral shell [fluorenes -9,9'- fluorenes], phenyl terphenyl, phenylnaphthalene and phenyl phenanthrene
1 valence residue of aromatic hydrocarbons.
The compound indicated by above-mentioned chemical formula 3 can be selected from following compounds.
Above-mentioned luminescent layer is further included in the present invention other than the compound comprising being indicated by above-mentioned chemical formula 1 and 3
Well known material of main part in technical field.As the concrete example of such material of main part, have aromatic fused ring derivative or
Nitrogen-containing heterocgcies etc..Specifically, as aromatic fused ring derivative, there are anthracene derivant, pyrene derivatives, naphthalene derivatives, simultaneously
Five benzene derivatives, phenanthrene compound, fluoranthene compound etc. have carbazole derivates, dibenzofurans derivative as nitrogen-containing heterocgcies
Object, ladder type furan compoundPyrimidine derivatives etc., but not limited to this.
As dopant material, have aromatic amine derivative, styrylamine compounds, boron complexes, fluoranthene compound,
Metal complex etc..Specifically, being the aromatic series with substituted or unsubstituted arylamino as aromatic amine derivative
Fused-ring derivatives, have pyrene with arylamino, anthracene,Two indeno pyrenes (Periflanthene) etc., as styryl amine
Compound is to replace to have the compound of at least one aryl vinyl on substituted or unsubstituted arylamine, by selected from aryl,
Substituent group more than one or two of silicyl, alkyl, naphthenic base and arylamino is substituted or unsubstituted.It is specific and
Speech, has styryl amine, styryl diamines, styryl triamine, styryl tetramine etc., but not limited to this.In addition,
As metal complex, there are complex of iridium, platinum complex etc., but not limited to this.
Above-mentioned electron transfer layer is from electron injecting layer reception electronics and by the layer of electron-transport to luminescent layer, as electronics
Transport materials are can to inject well electronics from cathode and transfer them to the substance of luminescent layer, the big object of electron mobility
Matter is suitable.As concrete example, there is the Al complex of 8-hydroxyquinoline, comprising Alq3Complex, organic free radical chemical combination
Object, flavonol-metal complex etc., but it is not limited only to this.Electron transfer layer can be as used in the prior art
It is used together with the cathode substance of any desired.In particular, the example of suitable cathode substance be with low work function and with
The common substance of aluminium layer or silver layer.Specially caesium, barium, calcium, ytterbium and samarium, in every case, with aluminium layer or silver layer.
Above-mentioned electron injecting layer is the layer for the electronics that injection carrys out self-electrode, preferably following compound: has transmission electronics
Ability, there is electron injection effect from cathode, for the excellent electron injection effect of luminescent layer or luminescent material, prevent
Only generated exciton is migrated to hole injection layer in luminescent layer, and film Forming ability is excellent.Specifically, have Fluorenone,
Anthraquinone bismethane (Anthraquinodimethane), diphenoquinone, thiopyrandioxide,Azoles,Diazole, triazole, imidazoles,
Tetrabasic carboxylic acid, fluorenylidene-methane, anthrone etc. and their derivative, metal complex and nitrogenous five-membered ring derivative
Deng but not limited to this.
As above-mentioned metal complex, there are 8-hydroxyquinoline lithium, bis- (8-hydroxyquinoline) zinc, bis- (8-hydroxyquinolines)
Copper, bis- (8-hydroxyquinoline) manganese, three (8-hydroxyquinoline) aluminium, three (2- methyl -8-hydroxyquinoline) aluminium, three (8-hydroxyquinolines)
Gallium, bis- (10- hydroxy benzo [h] quinoline) berylliums, bis- (10- hydroxy benzo [h] quinoline) zinc, bis- (2- methyl -8- quinoline) gallium chlorides,
Bis- (2- methyl -8- quinoline) (o-cresol) galliums, bis- (2- methyl -8- quinoline) (1- naphthols) aluminium, bis- (2- methyl -8- quinoline) (2-
Naphthols) gallium etc., but not limited to this.
According to used material, organic illuminating element according to the present invention can be top emission type, bottom emission type
Or bidirectional luminescence type.
The manufacture of above-mentioned organic illuminating element illustrates in the examples below.But following embodiments are to be used for
The present invention is illustrated, it's not limited to that for the scope of the present invention.
Embodiment 1: the manufacture of organic illuminating element
It will be withThickness be coated with ITO (tin indium oxide, indium tin oxide) glass substrate be put into it is molten
Solution has in the distilled water of detergent, is washed using ultrasonic wave.At this moment, detergent uses Fei Xier company (Fischer
Co.) product, distilled water have used filter (filter) filtering two using Millipore Corp. (Millipore Co.) manufacture
Secondary distilled water.After ito substrate is washed 30 minutes, it is repeated twice with distilled water and carries out 10 minutes ultrasonic washings.It is steaming
After distilled water is washed, after ito substrate isopropanol, acetone, methanol solvate are carried out ultrasonic washing and dried, it is delivered to
Gas ions cleaning machine.In addition, after five minutes by the cleaning of above-mentioned ito substrate, being delivered to vacuum evaporation plating machine using oxygen plasma.
In the ITO electrode prepared in this way, withThickness following compound HI-1 are subjected to thermal vacuum vapor deposition and shape
At hole injection layer.On above-mentioned hole injection layer, by following compound HT-1 withThickness carry out thermal vacuum vapor deposition
And form hole transmission layer, in above-mentioned cave transport layer, by following compound 2-1 withThickness carry out vacuum evaporation and
Form electronic barrier layer.Then, on above-mentioned electronic barrier layer, by the weight of following compound 1-1 and opposite above compound 1-1
Amount be the phosphorescent dopants YGD-1 of 6 weight % carry out total vapor deposition and withThickness formed luminescent layer.In above-mentioned luminescent layer
On, by following compound ET-1 withThickness carry out vacuum evaporation and form electron transfer layer, by following compound ET-
2 and the weight with respect to above compound ET-2 be 2 weight % Li carry out total vapor deposition and withThickness formed electronics note
Enter layer.On above-mentioned electron injecting layer, withThickness AM aluminum metallization and form cathode.
During above-mentioned, the evaporation rate of organic matter is maintainedAluminium maintainsVapor deposition
Speed, in vapor deposition, vacuum degree maintains 1 × 10-7~5 × 10-8Support, to make organic illuminating element.
Embodiment 2 to 16: the manufacture of organic illuminating element
The compound for being used to form electronic barrier layer and/or luminescent layer has been subjected to the change such as following table 1, except this with
Outside, organic illuminating element has been made by method identical with above-described embodiment 1.In following table 1,1-2,1-3,1-4,2-2,
2-3 and 2-4 compound difference is as follows.
Comparative example 1 to 15: the manufacture of organic illuminating element
The compound for being used to form electronic barrier layer and/or luminescent layer the change such as following table 1 is subjected to, except this it
Outside, organic illuminating element has been made by method identical with above-described embodiment 1.In following table 1, HT-2, HT-3, YGH-1
Distinguish with YGH-2 compound as follows.
Experimental example: the performance evaluation of organic illuminating element
In 10mA/cm2Current density under, measurement manufactures organic according to above-described embodiment 1 to 16 and comparative example 1 to 15
In voltage, efficiency and the service life of light-emitting component, it the results are shown in table 1.Above-mentioned service life (LT95) refers to reduction to original intensity
Time needed for the 95% of (6000nit), and in 20mA/cm2Current density under measure.
[table 1]
The organic illuminating element (comparative example 1 to 3) using existing compound is shown in above-mentioned table 1；Using by above-mentioned
The compound that chemical formula 2 indicates uses existing compound as the organic light emission of emitting layer material as electronic barrier layer
Element (comparative example 4 to 7)；And use the compound indicated by above-mentioned chemical formula 1 as emitting layer material, but using existing
Fundamental characteristics of the compound as the organic illuminating element (comparative example 8 to 11) of electronic blocking layer material.
Comparative example and comparative example it has been confirmed that use the compound indicated by above-mentioned chemical formula 1 and 2 as hair respectively
In the case where the material of photosphere and electronic barrier layer, compared with existing organic illuminating element, show low driving voltage, efficiently
Rate and long-life.In particular, use by above compound 2-2 as in the case where electronic blocking layer material, driving voltage is minimum,
Efficiency highest uses 1-3 as longest-lived in the case where emitting layer material.
On the other hand, comparative examples 1 to 15 are being indicated electronic barrier layer material altering by above-mentioned chemical formula 2
In the comparative example 4 to 7 of compound, comparative example 12 to 15, efficiency is improved, and is changed to by emitting layer material by above-mentioned chemical formula 1
In the comparative example 8 to 11 of the compound of expression, the service life is improved.But it can not show efficiency and the service life of embodiment level.
It thereby confirms that, organic illuminating element of the invention is between anode and luminescent layer comprising as shown in above-mentioned chemical formula 2
Replace the compound of the structure for the arylamine for having the key (L) comprising benzidine-type on No. 9 positions of carbazyl and shows and mention
High efficiency includes as shown in above-mentioned chemical formula 1 in No. 4 positions of the dibenzofuran group with electronic stability in luminescent layer
It sets the compound for the structure for replacing the triazine radical for having electron injection ability and thermal stability very excellent and shows low driving
The efficiency of voltage and raising, while showing the long-life.
Symbol description
1: substrate 2: anode
3: hole injection layer 4: cathode
5: hole transmission layer 6: electronic barrier layer
7: luminescent layer 8: electron transfer layer.
Claims (15)
1. a kind of organic illuminating element comprising: anode, and the cathode that has opposed with the anode and have in institute
One layer or more of organic matter layer between anode and cathode is stated,
The organic matter layer includes luminescent layer,
The luminescent layer includes the compound indicated by following chemical formula 1,
Compound between the anode and luminescent layer comprising being indicated by following chemical formula 2:
Chemical formula 1
In the chemical formula 1,
L1For singly-bound or substituted or unsubstituted C6-60Arlydene,
L2For singly-bound, substituted or unsubstituted C6-60Arlydene or substituted or unsubstituted 1 comprising in O, N, Si and S with
On C2-60Inferior heteroaryl,
Y1To Y3It is each independently N or C-R1, and at least any one is N, R1For hydrogen or substituted or unsubstituted C1-40Alkyl,
Ar1And Ar2It is each independently substituted or unsubstituted C6-60Aryl or it is substituted or unsubstituted include O, N, Si and S
In 1 or more C2-60Heteroaryl,
Ar3For substituted or unsubstituted C6-60Aryl,
The integer that m is 1 to 2,
Chemical formula 2
In the chemical formula 2,
Ar4And Ar5It is each independently substituted or unsubstituted C6-60Aryl,
R1And R2It is each independently substituted or unsubstituted C6-20Aryl,
N1 and n2 is each independently 0 or 1.
2. organic illuminating element according to claim 1, wherein L1For singly-bound or phenylene.
3. organic illuminating element according to claim 1, wherein Y1To Y3It is each independently N or C-H, and at least any
A is N.
4. organic illuminating element according to claim 1, wherein Ar1And Ar2It is each independently from selected from benzene, connection
Benzene, terphenyl, naphthalene, phenanthrene, triphenylene, 9,9- dimethyl fluorene, 9,9- diphenylfluorene, spiral shell [fluorenes -9,9'- fluorenes], dibenzofurans, two
Aromatic hydrocarbons in benzothiophene, N- phenyl carbazole, phenyl -9,9- dimethyl fluorene, phenyl dibenzofurans and phenyl dibenzothiophenes
Or 1 valence residue of heteroaryl hydrocarbon.
5. organic illuminating element according to claim 1, wherein L2For singly-bound or to derive from selected from benzene, naphthalene, 9,9-
Dimethyl fluorene, 9,9- diphenylfluorene, spiral shell [fluorenes -9,9'- fluorenes], dibenzofurans, dibenzothiophenes, benzothiophene are simultaneously [2,3-d]
Pyrimidine and the benzothiophene simultaneously divalent residue of the aromatic hydrocarbons in [3,2-d] pyrimidine or heteroaryl hydrocarbon.
6. organic illuminating element according to claim 1, wherein Ar3For from selected from benzene, biphenyl, terphenyl, naphthalene,
Anthracene, aphthacene,Phenanthrene, triphenylene, fluoranthene, pyrene and in aromatic hydrocarbons 1 valence residue.
7. organic illuminating element according to claim 1, wherein L2-Ar3For the substituent group in following substituent groups:
8. organic illuminating element according to claim 1, wherein the compound indicated by the chemical formula 1 is selected under
State the compound of chemical formula 1-1 and 1-2 expression:
Chemical formula 1-1
In the chemical formula 1-1,
L1、Y1To Y3、Ar1And Ar2It is identical as chemical formula 1,
L2aFor singly-bound, substituted or unsubstituted C6-60Arlydene or substituted or unsubstituted 1 comprising in O, N, Si and S
Above C2-60Inferior heteroaryl,
Ar3aFor substituted or unsubstituted C6-60Aryl,
Chemical formula 1-2
In the chemical formula 1-2,
L1、Y1To Y3、Ar1And Ar2It is identical as chemical formula 1,
L2bAnd L2cIt is each independently singly-bound, substituted or unsubstituted C6-60Arlydene or it is substituted or unsubstituted comprising O,
N, 1 or more C in Si and S2-60Inferior heteroaryl,
Ar3bAnd Ar3cIt is each independently substituted or unsubstituted C6-60Aryl.
9. organic illuminating element according to claim 1, wherein be selected from by the compound that the chemical formula 1 indicates following
Compound:
10. organic illuminating element according to claim 1, wherein Ar4And Ar5Be each independently from selected from benzene,
Biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, phenyl terphenyl, phenylnaphthalene, phenyl phenanthrene, 9,9- dimethyl fluorene, 9,9- diphenylfluorene and
1 valence residue of the aromatic hydrocarbons in spiral shell [fluorenes -9,9'- fluorenes].
11. organic illuminating element according to claim 1, wherein
R1And R2For phenyl,
N1 and n2 is each independently 0 or 1.
12. organic illuminating element according to claim 1, wherein be selected from by the compound that the chemical formula 2 indicates following
Compound:
13. organic illuminating element according to claim 1, wherein the luminescent layer also includes to be indicated by following chemical formula 3
Compound:
Chemical formula 3
In the chemical formula 3,
Ar7And Ar8It is each independently substituted or unsubstituted C6-60Aryl.
14. organic illuminating element according to claim 13, wherein Ar7And Ar8Be each independently from selected from benzene,
Biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, 9,9- dimethyl fluorene, 9,9- diphenylfluorene, spiral shell [fluorenes -9,9'- fluorenes], phenyl terphenyl,
1 valence residue of phenylnaphthalene and the aromatic hydrocarbons in phenyl phenanthrene.
15. organic illuminating element according to claim 13, wherein be selected from down by the compound that the chemical formula 3 indicates
State compound:
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2017-0089708 | 2017-07-14 | ||
| KR20170089708 | 2017-07-14 | ||
| PCT/KR2018/004873 WO2019013435A1 (en) | 2017-07-14 | 2018-04-26 | Organic light-emitting device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110268036A true CN110268036A (en) | 2019-09-20 |
| CN110268036B CN110268036B (en) | 2022-12-20 |
Family
ID=65002662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201880010433.1A Active CN110268036B (en) | 2017-07-14 | 2018-04-26 | Organic light emitting element |
Country Status (3)
| Country | Link |
|---|---|
| KR (1) | KR102118629B1 (en) |
| CN (1) | CN110268036B (en) |
| WO (1) | WO2019013435A1 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110366554A (en) * | 2017-07-20 | 2019-10-22 | 株式会社Lg化学 | New heterocyclic compound and the organic luminescent device using it |
| CN113678274A (en) * | 2019-11-11 | 2021-11-19 | 株式会社Lg化学 | Organic light emitting device |
| WO2022100194A1 (en) * | 2020-11-10 | 2022-05-19 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, organic electroluminescent device, and electronic device |
| CN114621198A (en) * | 2020-12-11 | 2022-06-14 | 北京夏禾科技有限公司 | Organic electroluminescent material and device thereof |
| JP2022534887A (en) * | 2020-03-11 | 2022-08-04 | エルジー・ケム・リミテッド | organic light emitting device |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200093442A (en) | 2019-01-28 | 2020-08-05 | 주식회사 엘지화학 | Organic light emitting device |
| CN110429187B (en) * | 2019-07-05 | 2020-12-08 | 武汉华星光电半导体显示技术有限公司 | Thin film electroluminescent device, preparation method thereof and electronic equipment |
| CN111533678B (en) * | 2019-07-19 | 2021-07-20 | 南京高光半导体材料有限公司 | High-efficiency electron blocking material and organic electroluminescent device using same |
| CN113994496A (en) * | 2020-03-11 | 2022-01-28 | 株式会社Lg化学 | Organic light emitting device |
| CN115191039A (en) * | 2020-05-14 | 2022-10-14 | 株式会社Lg化学 | Organic light emitting device |
| KR20220058419A (en) * | 2020-10-30 | 2022-05-09 | 엘티소재주식회사 | Heterocyclic compound, organic light emitting device comprising the same, composition for organic layer of organic light emitting device, manufacturing method of the organic light emitting device |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150074603A (en) * | 2013-12-24 | 2015-07-02 | 희성소재 (주) | Fluorene-based compound and organic light emitting device using the same |
| CN106459018A (en) * | 2014-05-05 | 2017-02-22 | 默克专利有限公司 | Materials for organic light emitting devices |
| KR101744248B1 (en) * | 2016-09-06 | 2017-06-07 | 주식회사 엘지화학 | Organic light emitting device |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100430549B1 (en) | 1999-01-27 | 2004-05-10 | 주식회사 엘지화학 | New organomattalic complex molecule for the fabrication of organic light emitting diodes |
| KR20160027940A (en) * | 2014-09-02 | 2016-03-10 | 주식회사 엘지화학 | Organic light emitting device |
| KR101614738B1 (en) * | 2015-11-02 | 2016-04-22 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| JP6754185B2 (en) * | 2015-12-10 | 2020-09-09 | コニカミノルタ株式会社 | Organic functional materials for organic electroluminescence devices, display devices, lighting devices and electronic devices |
-
2018
- 2018-04-26 CN CN201880010433.1A patent/CN110268036B/en active Active
- 2018-04-26 KR KR1020180048665A patent/KR102118629B1/en active IP Right Grant
- 2018-04-26 WO PCT/KR2018/004873 patent/WO2019013435A1/en active Application Filing
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150074603A (en) * | 2013-12-24 | 2015-07-02 | 희성소재 (주) | Fluorene-based compound and organic light emitting device using the same |
| CN106459018A (en) * | 2014-05-05 | 2017-02-22 | 默克专利有限公司 | Materials for organic light emitting devices |
| KR101744248B1 (en) * | 2016-09-06 | 2017-06-07 | 주식회사 엘지화학 | Organic light emitting device |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11578076B2 (en) | 2017-07-20 | 2023-02-14 | Lg Chem, Ltd. | Heterocyclic compound and organic light emitting device using the same |
| US11840538B2 (en) | 2017-07-20 | 2023-12-12 | Lg Chem, Ltd. | Heterocyclic compounds and organic light emitting device using the same |
| CN110366554A (en) * | 2017-07-20 | 2019-10-22 | 株式会社Lg化学 | New heterocyclic compound and the organic luminescent device using it |
| US11518769B2 (en) | 2017-07-20 | 2022-12-06 | Lg Chem, Ltd. | Heterocyclic compounds and organic light emitting device using the same |
| CN110366554B (en) * | 2017-07-20 | 2022-12-27 | 株式会社Lg化学 | Heterocyclic compound and organic light-emitting device using the same |
| CN113678274A (en) * | 2019-11-11 | 2021-11-19 | 株式会社Lg化学 | Organic light emitting device |
| CN113678274B9 (en) * | 2019-11-11 | 2023-10-24 | 株式会社Lg化学 | Organic light emitting device |
| CN113678274B (en) * | 2019-11-11 | 2023-09-12 | 株式会社Lg化学 | Organic light emitting device |
| JP7293565B2 (en) | 2020-03-11 | 2023-06-20 | エルジー・ケム・リミテッド | organic light emitting device |
| JP2022534887A (en) * | 2020-03-11 | 2022-08-04 | エルジー・ケム・リミテッド | organic light emitting device |
| WO2022100194A1 (en) * | 2020-11-10 | 2022-05-19 | 陕西莱特光电材料股份有限公司 | Nitrogen-containing compound, organic electroluminescent device, and electronic device |
| DE102021132671A1 (en) | 2020-12-11 | 2022-06-15 | Beijing Summer Sprout Technology Co., Ltd. | Organic electroluminescent material and device made therefrom |
| CN114621198A (en) * | 2020-12-11 | 2022-06-14 | 北京夏禾科技有限公司 | Organic electroluminescent material and device thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| KR102118629B1 (en) | 2020-06-03 |
| WO2019013435A1 (en) | 2019-01-17 |
| KR20190008073A (en) | 2019-01-23 |
| CN110268036B (en) | 2022-12-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110268036A (en) | Organic illuminating element | |
| CN110313078A (en) | Organic luminescent device | |
| CN105308035B (en) | Heterocyclic compound and the Organic Light Emitting Diode for including it | |
| CN105431423B (en) | Heterocyclic compound and the organic luminescent device for including the compound | |
| CN108336239A (en) | Organic illuminating element | |
| CN108352449A (en) | Organic luminescent device | |
| CN110495005A (en) | Organic illuminating element | |
| CN108137527A (en) | Noval chemical compound and the Organic Light Emitting Diode for including it | |
| CN109564972A (en) | Organic illuminating element | |
| CN109564973A (en) | Organic luminescent device | |
| CN107641116A (en) | Polycyclic compound and the organic illuminating element for including it | |
| CN108063188B (en) | Organic light emitting element | |
| CN108603106A (en) | Organic luminescent device | |
| CN109641916A (en) | Heterocyclic compound and organic luminescent device comprising it | |
| CN107459478A (en) | Compound and the organic electronic element for including it | |
| CN107614494A (en) | Spiro-compound and the organic luminescent device for including it | |
| CN107759638A (en) | New organo-metallic compound and utilize its organic illuminating element | |
| CN107778260A (en) | Novel organic luminescent material and the organic illuminating element for including it | |
| CN109790131A (en) | Heterocyclic compound and organic luminescent device comprising it | |
| CN110225909A (en) | New heterocyclic compound and the organic luminescent device comprising it | |
| CN110382476A (en) | Heterocyclic compound and organic illuminating element comprising it | |
| CN110475769A (en) | Heterocyclic compound and organic illuminating element comprising it | |
| CN107428701A (en) | Heterocyclic compound and the organic luminescent device for including it | |
| CN110520417A (en) | Heterocyclic compound and the organic illuminating element for utilizing it | |
| CN107311987A (en) | Compound and the organic electronic element comprising it |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |