CN106167463A - Aromatic amine compounds and preparation method thereof and the organic luminescent device being made up of this compound - Google Patents
Aromatic amine compounds and preparation method thereof and the organic luminescent device being made up of this compound Download PDFInfo
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- CN106167463A CN106167463A CN201610579074.4A CN201610579074A CN106167463A CN 106167463 A CN106167463 A CN 106167463A CN 201610579074 A CN201610579074 A CN 201610579074A CN 106167463 A CN106167463 A CN 106167463A
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- 0 CC(C)CC(N1C(C=C)=C*)=I[*@@](C)(*)C=C*=C[C@@]1S Chemical compound CC(C)CC(N1C(C=C)=C*)=I[*@@](C)(*)C=C*=C[C@@]1S 0.000 description 6
- WOMHIYNMBZDWQY-UHFFFAOYSA-N C1C=CC=C2C1C=CC=CC2 Chemical compound C1C=CC=C2C1C=CC=CC2 WOMHIYNMBZDWQY-UHFFFAOYSA-N 0.000 description 1
- ADPYSZNUBWNLDH-GVHYBUMESA-N C[C@@H]1C=CC(C)CC1 Chemical compound C[C@@H]1C=CC(C)CC1 ADPYSZNUBWNLDH-GVHYBUMESA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- 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
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- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- 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
Abstract
The present invention relates to a kind of aromatic amine compounds and preparation method thereof and the organic luminescent device being made up of this compound, belong to electroluminescent organic material technical field.Solve existing aromatic amine compounds as heat stability during electroluminescent material, quick hole degree of excursion, luminous body efficiency and life-span the most poor technical problem.Luminous efficiency and the life characteristic of organic luminescent device prepared by the aromatic amine compounds that the present invention provides all increase significantly, better heat stability.The organic luminescent device that aromatic amine compounds prepared by the method utilizing the present invention to provide is made can be applicable to the high OLED industry of practicality, flat panel shows, planar illuminant, illumination face illuminating OLED luminous body, flexible luminous body, photocopier, printer, LCD backlight lamp or the light source of dosing machine class, display panel, mark etc., there is good application prospect.
Description
Technical field
The present invention relates to electroluminescent organic material technical field, be specifically related to a kind of aromatic amine compounds and system thereof
Preparation Method and the organic luminescent device being made up of this compound.
Background technology
Since Tang in 1987 etc. are successfully prepared the small molecule light emitters part of low-voltage driving, organic light emission technology achieved with
Huge progress, and initially enter industrialization process；Wherein, the performance of organic luminescent device is risen by electroluminescent organic material
Very important effect.
According to the size of electroluminescent organic material molecular weight, little molecule organic electroluminescent material and high score can be divided into
Sub-electroluminescent organic material.In presently disclosed luminescent material, due to the fluorescence quantum efficiency of small molecule electroluminescent material
Height, is easily purified, and luminosity and excitation are also superior to macromolecular material.So small molecule electroluminescent materials application is in luminescence
Device has started to realize commercialization.
Aromatic amine compounds is the little molecule organic electroluminescent material that a class is important, such as TPD, α-NPD and public affairs
Compound disclosed in the number of opening US20150014657:
But, these aromatic amine compounds presently disclosed as heat stability during electroluminescent material, quickly
Hole degree of excursion, luminous body efficiency and life-span are the most poor.
Summary of the invention
The invention solves the problems that existing aromatic amine compounds is as heat stability during electroluminescent material, quick hole
The technical problem that degree of excursion, luminous body efficiency and life-span are the most poor, it is provided that a kind of new aromatic amine compounds and system thereof
Preparation Method and the organic luminescent device being made up of this compound.
In order to solve above-mentioned technical problem, technical scheme is specific as follows:
A kind of aromatic amine compounds, the general molecular formula of this compound is as shown in [chemical formula 1]:
[chemical formula 1]
In formula, Ar1And Ar2It is each independently selected from substituted or unsubstituted phenyl, xenyl, substituted or unsubstituted
The fused ring aryl of C10-C14 or N-phenyl-3-carbazyl.
In technique scheme, described aromatic amine compounds is the specific knot shown in chemical formula [2-1～2-11]
The compound of structure:
[chemical formula 2-1]
[chemical formula 2-2]
[chemical formula 2-3]
[chemical formula 2-4]
[chemical formula 2-5]
[chemical formula 2-6]
[chemical formula 2-7]
[chemical formula 2-8]
[chemical formula 2-9]
[chemical formula 2-10]
[chemical formula 2-11]
In formula, R1And R2It is each independently selected from hydrogen, cyano group or halogen.
In technique scheme, described aromatic amine compounds is concrete shown in chemical formula [A-1～A-72]
Compound:
The preparation method of a kind of aromatic amine compounds, comprises the following steps:
Take the bromo-3,5-of 3'-bis-(9-carbazole) biphenyl, containing Ar1And Ar2The amino-compound of substituent group, sodium tert-butoxide, three (two
BENZYLIDENE ACETONE) two palladiums and tri-butyl phosphine, dissolve them in the toluene solvant of 100mL, 60 DEG C of stirring 3h, nitrogen is protected
Protecting, after TLC monitoring reaction terminates, be cooled to room temperature, after extracting with dichloromethane and water, organic facies anhydrous magnesium sulfate is dried
After be evaporated, product column chromatography obtains aromatic amine compounds.
In technique scheme, the concrete preparation method of described 3'-bromo-3,5-bis-(9-carbazole) biphenyl is: 1-bromo-3-fluorobenzene
8.9mmol, (3,5-bis-(9H-carbazole-9-base) phenyl) boric acid 9.8mmol, tetra-triphenylphosphine palladium 0.3mmol and potassium carbonate
0.02mol is dissolved in the toluene of 100mL: H2In O=2:1 mixed solvent, 80 DEG C of stirring 5h, nitrogen is protected, and treats TLC monitoring reaction
After end, being cooled to room temperature, after extracting with dichloromethane and water, organic facies anhydrous magnesium sulfate is evaporated after drying, product column chromatography
Obtain the bromo-3,5-of 3'-bis-(9-carbazole) biphenyl.
The organic luminescent device being made up of aromatic amine compounds of the present invention, including the first electrode, the second electrode
And the one or more organic compound layers being placed between described two electrodes, it is characterised in that at least one organic compound layer
Comprise at least one described aromatic amine compounds.
Above-mentioned aromatic amine compounds is single form or with other material mixed forms are included in above-mentioned organic compound
In nitride layer.
Above-mentioned organic compound layer at least a part of which includes hole injection layer, hole transmission layer, not only possesses hole injection but also have
Standby hole transport technical ability layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, electron injecting layer and both possessed electricity
Son transmission possesses again electronics and injects any one layer in technical ability layer.
Above-mentioned hole injection layer, hole transmission layer, not only possess hole and inject but also possess in hole transport technical ability layer at least one
Individual it be usual hole injecting material, hole transporting material and not only possessed hole and inject but also possess beyond hole transport technical ability layer material
Including being electronically generated material.
In the present invention, " organic compound layer " refers to deployment between organic luminescent device the first electrode and the second electrode
All terms of layer.
Such as, above-mentioned organic compound layer includes that luminescent layer, above-mentioned organic compound layer include phosphorescence host, fluorescence master
In the doping of body, phosphorescence and fluorescence doping more than one, the most above-mentioned luminescent layer includes described aromatic amine compounds, i) on
Stating fluorescent host can be above-mentioned aromatic amine compounds；Ii) doping of above-mentioned fluorescence can be above-mentioned aromatic amine chemical combination
Thing；Iii) above-mentioned fluorescent host and fluorescence doping can be above-mentioned aromatic amine compounds.
Above-mentioned luminescent layer can be red, yellow or cyan luminescent layer.Such as, above-mentioned aromatic amine during above-mentioned luminescent layer cyan
Compound uses in cyan main body or cyan doping purposes, it is provided that high efficiency, high brightness, high-resolution and long-life organic luminescent device.
And above-mentioned organic compound level includes that electron transfer layer, above-mentioned electron transfer layer include above-mentioned aromatic amine
Compound.The most above-mentioned electron transfer layer is to include the compound containing metal again beyond above-mentioned aromatic amine compounds.
Above-mentioned organic compound layer includes that luminescent layer and electron transfer layer, above-mentioned luminescent layer and electron transfer layer include respectively
(the above-mentioned aromatic amine compounds that above-mentioned luminescent layer and electron transfer layer include can phase for above-mentioned aromatic amine compounds
Together can also be different).
Above-mentioned organic luminescent device utilizes beyond the aromatic amine compounds of chemical formula 1, with common organic electronic device
Part manufacture method and materials synthesis.
Another aspect of the present invention is that above-mentioned device can be used in organic luminescent device (OLED), organic sun with same principle
Battery (OSC), Electronic Paper (e-paper), Organophotoreceptor (OPC) or OTFT (OTFT).
Organic luminescent device is to utilize gold evaporation on the method substrates such as film vapor deposition, electron beam evaporation, physical vapour deposition (PVD)
Belonging to and have oxide and their alloy formation anode of electric conductivity, layer, luminescent layer, hole are passed in hole injection layer, hole
The method synthesis of evaporation cathode after barrier layer and electron transfer layer.Beyond above method, on substrate, cathode substance starts organic
Compound layer, anode material are deposited with making organic luminescent device in order.
Above-mentioned organic compound layer can include that layer, luminescent layer, hole blocking layer and electronics are passed in hole injection layer, hole
The multiple structure of transport layer, and above-mentioned organic compound layer is to use various macromolecular material solvent engineering to substitute evaporation side
Method, such as, spin-coating (spin-coating), strip molding (tape-casting), scraping blade method (doctor-blading),
The methods such as silk screen printing (Screen-Printing), ink jet printing or thermal imaging (Thermal-Imaging) reduce number of plies manufacture.
Organic luminescent device according to the present invention is can also the most luminous, back side illuminated or lighting at two sides by the material used.
The aromatic amine compounds that the present invention provides is applicable to organic photovoltaic cell, illumination OLED, flexibility OLED, organic
In the organic assembly such as photoreceptor, organic transistor, it is also possible to be suitable for the device of similar principle be applicable to organic luminescent device.
The invention has the beneficial effects as follows:
Luminous efficiency and the life characteristic of organic luminescent device prepared by the aromatic amine compounds that the present invention provides are equal
Increase significantly, better heat stability.
The organic luminescent device that aromatic amine compounds prepared by the method utilizing the present invention to provide is made can be applicable to
OLED industry, flat panel that practicality is high show, planar illuminant, illumination face illuminating OLED luminous body, flexible luminous body,
Photocopier, printer, LCD backlight lamp or the light source of dosing machine class, display panel, mark etc., have good application prospect.
Detailed description of the invention
The aromatic amine compounds that the present invention provides is raw material with 3'-bromo-3,5-bis-(9-carbazole) biphenyl, and connection contains
Ar1And Ar2The amino-compound of substituent group, generates the aromatic amine compounds containing different substituents, and synthetic route is as follows:
Embodiment 1
The preparation of the bromo-3,5-of intermediate 3'-bis-(9-carbazole) biphenyl:
1-bromo-3-fluorobenzene 8.9mmol, (3,5-bis-(9H-carbazole-9-base) phenyl) boric acid 9.8mmol, tetra-triphenylphosphine palladium
0.3mmol and potassium carbonate 0.02mol is dissolved in the toluene of 100mL: H2In O=2:1 mixed solvent, 80 DEG C of stirring 5h, nitrogen is protected
Protecting, after TLC monitoring reaction terminates, be cooled to room temperature, after extracting with dichloromethane and water, organic facies anhydrous magnesium sulfate is dried
After be evaporated, product column chromatography obtains 3'-bromo-3,5-bis-(9-carbazole) biphenyl 7.92mmol, productivity 89%.Mass spectrum: 563.52.
The synthesis of final products aromatic amine compounds (A-1):
By bromo-for 3'-3,5-bis-(9-carbazole) biphenyl 8.9mmol, diphenylamines 9.8mmol, sodium tert-butoxide 26.6mmol, three (two
BENZYLIDENE ACETONE) two palladium 0.4mmol and tri-butyl phosphine (50%) 0.9mmol are dissolved in the toluene solvant of 100mL, 60 DEG C of stirrings
3h, nitrogen is protected, and after TLC monitoring reaction terminates, is cooled to room temperature, organic facies anhydrous slufuric acid after extracting with dichloromethane and water
Magnesium is evaporated after drying, and product column chromatography obtains aromatic amine compounds (A-1) 8.01mmol, productivity 90%.Mass spectrum: 651.80.
Embodiment 2-72
The synthetic method of embodiment 2-72 is same as in Example 1, the reacting substance of each embodiment, generation material and productivity
Collect (being shown in Table 1).
Table 1 embodiment 2-72 reacting substance, generation material and productivity collect
Organic luminescent device prepares embodiment:
By Fisher Co., Ltd's coating layer thickness it isIto glass substrate be placed in distilled water cleaning 2 times, ultrasound wave is washed
Washing 30 minutes, repeatedly clean with distilled water 2 times, ultrasonic washing 10 minutes, distilled water cleans after terminating, isopropanol, acetone, first
It is dried after alcohol equal solvent ultrasonic washing in order, transfers in plasma washing machine, aforesaid substrate is washed 5 minutes,
Deliver in evaporator.
The ito glass substrate being already prepared to is deposited with hole injection layer 2-TNATA evaporationHole transmission layer
Aromatic amine compounds prepared by the embodiment described in a-NPD or table 2Blue main body A ND (double (the 2-naphthalene of 9,10-
Base) anthracene), dopant material TPPDA (N1, N1, N6, N6-tetraphenyl pyrene-1,6-diamidogen) 5% mixingThickness evaporation, hole
Barrier layer and hole transmission layer TPBiNegative electrode LiFAlSaid process organic matter vaporization plating speed is to maintain/ sec, LiF are/ sec, Al are /sec。
The organic luminescent device present invention prepared uses KEITHLEY Keithley 2400 type source measuring unit, CS-
2000 spectroradio luminance meters are tested, to evaluate the driving voltage of luminescent device, luminosity, luminous efficiency and luminous face
Color；The characteristics of luminescence test result of the device obtained is shown in Table 2, the aromatic amine chemical combination that table 2 is prepared for the embodiment of the present invention
Thing and compare the characteristics of luminescence test result of luminescent device prepared by material.
The characteristics of luminescence of table 2 device
Can find out prepared by the aromatic amine compounds with chemical formula 1 structure that the present invention provides from table 2 result
Luminous efficiency and the life characteristic of organic luminescent device all increase significantly.
The present invention utilizes the organic luminescent device of aromatic amine compounds can obtain luminous efficiency and the life-span is good
As a result, therefore can be applicable to the OLED industry that practicality is high.The organic luminescent device of the present invention be applicable to flat panel show,
Planar illuminant, illumination face illuminating OLED luminous body, flexible luminous body, photocopier, printer, LCD backlight lamp or dosing machine
The light source of class, display panel, mark etc..
The explanation of above example is only applicable to help to understand method and the core concept thereof of the present invention.It is right to it should be pointed out that,
For those skilled in the art, under the premise without departing from the principles of the invention, it is also possible to the present invention is carried out
Some improvement and modification, these improve and modify in the protection domain also falling into the claims in the present invention.
Claims (6)
1. an aromatic amine compounds, it is characterised in that the general molecular formula of this compound is as shown in [chemical formula 1]:
[chemical formula 1]
In formula, Ar1And Ar2It is each independently selected from substituted or unsubstituted phenyl, xenyl, substituted or unsubstituted C10-C14
Fused ring aryl or N-phenyl-3-carbazyl.
Aromatic amine compounds the most according to claim 1, it is characterised in that described aromatic amine compounds is for changing
The compound of the ad hoc structure shown in formula [2-1～2-11]:
[chemical formula 2-1]
[chemical formula 2-2]
[chemical formula 2-3]
[chemical formula 2-4]
[chemical formula 2-5]
[chemical formula 2-6]
[chemical formula 2-7]
[chemical formula 2-8]
[chemical formula 2-9]
[chemical formula 2-10]
[chemical formula 2-11]
In formula, R1And R2It is each independently selected from hydrogen, cyano group or halogen.
Aromatic amine compounds the most according to claim 1, it is characterised in that described aromatic amine compounds is for changing
Concrete compound shown in formula [A-1～A-72]:
4. according to the preparation method of the aromatic amine compounds described in claim 1-3 any one, it is characterised in that include
Following steps:
Take the bromo-3,5-of 3'-bis-(9-carbazole) biphenyl, containing Ar1And Ar2The amino-compound of substituent group, sodium tert-butoxide, three (two benzal
Benzylacetone) two palladiums and tri-butyl phosphine, dissolve them in the toluene solvant of 100mL, 60 DEG C of stirring 3h, nitrogen is protected, is treated
After TLC monitoring reaction terminates, being cooled to room temperature, after extracting with dichloromethane and water, organic facies anhydrous magnesium sulfate steams after drying
Dry, product column chromatography obtains aromatic amine compounds.
The preparation method of aromatic amine compounds the most according to claim 4, it is characterised in that described 3'-bromo-3,5-
The concrete preparation method of two (9-carbazole) biphenyl is: 1-bromo-3-fluorobenzene 8.9mmol, (3,5-bis-(9H-carbazole-9-base) phenyl) boric acid
9.8mmol, tetra-triphenylphosphine palladium 0.3mmol and potassium carbonate 0.02mol are dissolved in the toluene of 100mL: H2O=2:1 mixed solvent
In, 80 DEG C of stirring 5h, nitrogen is protected, and after TLC monitoring reaction terminates, is cooled to room temperature, has after extracting with dichloromethane and water
Machine anhydrous magnesium sulfate is evaporated after drying, and product column chromatography obtains 3'-bromo-3,5-bis-(9-carbazole) biphenyl.
6. the organic luminescent device being made up of aromatic amine compounds described in claim 1-3 any one, including the first electricity
Pole, the second electrode and the one or more organic compound layers being placed between described two electrodes, it is characterised in that at least one has
Machine compound layer comprises at least one described aromatic amine compounds.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019101719A1 (en) | 2017-11-23 | 2019-05-31 | Merck Patent Gmbh | Materials for electronic devices |
| US20200295269A1 (en) * | 2019-03-11 | 2020-09-17 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
| CN113121493A (en) * | 2021-04-13 | 2021-07-16 | 吉林奥来德光电材料股份有限公司 | Arylamine compound, preparation method thereof, organic electroluminescent device and display device |
| CN113416164A (en) * | 2020-04-28 | 2021-09-21 | 江苏三月科技股份有限公司 | Carbazole-containing organic compound and application thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1895004A (en) * | 2003-12-15 | 2007-01-10 | 出光兴产株式会社 | Material for organic electroluminescent element and organic electroluminescent element using same |
| JP2007180148A (en) * | 2005-12-27 | 2007-07-12 | Konica Minolta Holdings Inc | Organic electroluminescence element, material thereof, display and illumination apparatus |
| KR20160072373A (en) * | 2014-12-12 | 2016-06-23 | 원광대학교산학협력단 | Triphenylamine derivative for hole-trasporting of organic light-emitting diode and method for preparing the same |
| WO2016105138A2 (en) * | 2014-12-26 | 2016-06-30 | 주식회사 두산 | Organic compound and organo-electroluminescent device including same |
-
2016
- 2016-07-22 CN CN201610579074.4A patent/CN106167463A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1895004A (en) * | 2003-12-15 | 2007-01-10 | 出光兴产株式会社 | Material for organic electroluminescent element and organic electroluminescent element using same |
| JP2007180148A (en) * | 2005-12-27 | 2007-07-12 | Konica Minolta Holdings Inc | Organic electroluminescence element, material thereof, display and illumination apparatus |
| KR20160072373A (en) * | 2014-12-12 | 2016-06-23 | 원광대학교산학협력단 | Triphenylamine derivative for hole-trasporting of organic light-emitting diode and method for preparing the same |
| WO2016105138A2 (en) * | 2014-12-26 | 2016-06-30 | 주식회사 두산 | Organic compound and organo-electroluminescent device including same |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019101719A1 (en) | 2017-11-23 | 2019-05-31 | Merck Patent Gmbh | Materials for electronic devices |
| US11832513B2 (en) | 2017-11-23 | 2023-11-28 | Merck Patent Gmbh | Materials for electronic devices |
| US20200295269A1 (en) * | 2019-03-11 | 2020-09-17 | Samsung Display Co., Ltd. | Heterocyclic compound and organic light-emitting device including the same |
| CN113416164A (en) * | 2020-04-28 | 2021-09-21 | 江苏三月科技股份有限公司 | Carbazole-containing organic compound and application thereof |
| CN113121493A (en) * | 2021-04-13 | 2021-07-16 | 吉林奥来德光电材料股份有限公司 | Arylamine compound, preparation method thereof, organic electroluminescent device and display device |
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