CN108003121A - A kind of phenanthrene class compound and application thereof and organic electroluminescence device - Google Patents
A kind of phenanthrene class compound and application thereof and organic electroluminescence device Download PDFInfo
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- CN108003121A CN108003121A CN201711318031.1A CN201711318031A CN108003121A CN 108003121 A CN108003121 A CN 108003121A CN 201711318031 A CN201711318031 A CN 201711318031A CN 108003121 A CN108003121 A CN 108003121A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- H—ELECTRICITY
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- 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
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- H—ELECTRICITY
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- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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Abstract
The present invention provides a kind of luxuriant and rich with fragrance class compound, it is with following structural formula：The phenanthrene class compound has preferable heat endurance, high-luminous-efficiency, high luminance purity and low driving voltage, can be applied to organic electroluminescence device, organic solar batteries, perovskite battery, Organic Thin Film Transistors or organophotoreceptorswith field.Present invention also offers a kind of organic electroluminescence device, the device includes anode, cathode and organic layer, organic layer includes at least one layer in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, the at least one layer compound contained such as structural formula I in organic layer, the organic electroluminescence device made of luxuriant and rich with fragrance class compound have higher luminous efficiency and optical purity.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of phenanthrene class compound and application thereof, further relates to
A kind of organic electroluminescence device.
Background technology
Organic electroluminescence device (OLEDs) is by spin coating or vacuum evaporation deposition one between two metal electrodes
The device that layer organic material is prepared, a classical three layer organic electroluminescence device include hole transmission layer, luminescent layer
And electron transfer layer.The electronics produced by cathode is followed to be incorporated in through electron transfer layer through hole transmission layer by the hole that anode produces
Luminescent layer forms exciton, then shines.Organic electroluminescence device can be adjusted as desired by the material for changing luminescent layer
Section launches the light of various needs.
Organic electroluminescence device has self-luminous, wide viewing angle, low energy consumption, efficiency as a kind of new Display Technique
High, thin, rich in color, fast response time, Applicable temperature scope are wide, low driving voltage, can make flexible with it is transparent
Display panel and the particular advantages such as environmental-friendly, can apply on flat-panel monitor and a new generation's illumination, can also conduct
The backlight of LCD.
Since the invention at the bottom of the 1980s, organic electroluminescence device has industrially been applied, such as
As screens such as camera and mobile phones, but current OLED device, since efficiency is low, it is wider that the factors such as service life is short restrict it
General application, particularly large screen display, it is therefore desirable to improve the efficiency of device.And restrict one of key factor just
It is the performance of the electroluminescent organic material in organic electroluminescence device.It is voltage-operated in application additionally, due to OLED device
When, Joule heat can be produced so that organic material easily crystallizes, and have impact on service life and the efficiency of device, therefore, it is also desirable to
Develop the electroluminescent organic material of stability and high efficiency.
In organic electroluminescence device, the introducing of hole mobile material and injection material, can be effectively reduced positive electricity
Lotus is transferred to the ability of luminescent layer from cathode, improves efficiency and the thermostabilization of device.Traditional hole-injecting material, such as Copper
Phthalocyanine (CuPc), degraded is slow, prepares energy consumption height, is unfavorable for environmental protection, and it can absorb light, influence device
Efficiency.Hole mobile material original NPB etc., heat endurance is poor, also largely influences device lifetime.Thus, need
Develop the electroluminescent organic material of efficient stable.
The content of the invention
The present invention provides a kind of luxuriant and rich with fragrance class compound, it is the compound with following structural formula I：
Wherein Ar1And Ar2Independently selected from substitution or the aryl of unsubstituted C6-C30；
R1And R2Independently selected from the aryl of the alkyl of C1-C12, substitution or unsubstituted C6-C30；
A is selected from O, S or Se.
Optionally, Ar1And Ar2Independently selected from phenyl, naphthyl, xenyl, three and phenyl, anthryl, phenanthryl, pyrenyl,
Base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,9- bis- substitutes or unsubstituted aryl) fluorenyl, 9,9- be Spirofluorene-based, substitution or
The unsubstituted dibenzothiophene of person, substitution or unsubstituted dibenzofuran group, above aryl can also be further C1-
The alkyl substitution of C12.
Optionally, R1And R2Independently selected from hydrogen, methyl, ethyl, propyl group, isopropyl, butyl, phenyl, aminomethyl phenyl or connection
Phenyl.
Further alternative, luxuriant and rich with fragrance class compound is the compound of following structural 1-36：
The luxuriant and rich with fragrance class compound of the present invention can be reacted by Buchwald-Hartwig and ullmann reaction is prepared.
The luxuriant and rich with fragrance class compound of the present invention can be applied to organic electroluminescence device, organic solar batteries, perovskite electricity
Pond, Organic Thin Film Transistors or organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, which includes anode, cathode and organic layer, organic layer
Comprising one or more layers in luminescent layer, hole injection layer, hole transmission layer, exciton barrier-layer, electron transfer layer, wherein
Contain the luxuriant and rich with fragrance class compound as described in structural formula I at least one layer in the organic layer.
Wherein organic layer is hole transmission layer and luminescent layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and exciton
Barrier layer；
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and exciton barrier-layer；
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and exciton barrier-layer；
Optionally, the layer where the luxuriant and rich with fragrance class compound as described in structural formula I is hole transmission layer；
Optionally, the compound containing one or more kinds of structural formula 1-36 in hole transmission layer.
When luxuriant and rich with fragrance class compound as described in structural formula I is used for luminescent device and prepares, can be used alone, can also with it is other
Compound is used in mixed way；Luxuriant and rich with fragrance class compound as described in structural formula I can be used alone a kind of compound therein, can also be same
When use two or more the compound in structural formula I.
The gross thickness of the organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
When having the compound of structural formula I using the present invention, can arrange in pairs or groups makes the organic electroluminescence device of the present invention
With other materials, such as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and exciton barrier-layer
It is medium, and obtain blue and green light, yellow light, feux rouges or white light.
The hole transmission layer and hole injection layer of organic electroluminescence device of the present invention, material requested have good hole
Transmission performance, can effectively be transferred to hole on luminescent layer from anode.There is compound described in structural formula I except above-mentioned
Outside, other small molecules and macromolecular organic compound can also be included, include but not limited to carbazole compound, triaromatic amine
Compound, benzidine compound, compound of fluorene class, phthalocyanine-like compound, six cyano group, six miscellaneous triphen (hexanitrilehexaaza
Triphenylene tetra- cyanogen dimethyl-parabenzoquinone (F4-TCNQ) of), tetra- fluoro- 7,7' of 2,3,5,6-, 8,8'-, polyvinyl carbazole,
Polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of the organic electroluminescence device of the present invention, has the good characteristics of luminescence, can adjust as needed
The scope of visible ray.In addition to the compound of fluorene class that can contain the present invention, following compound can also be contained, including it is but unlimited
In naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance class compound,Class compound, phenol piperazine class compound, anthracene class
Compound, pentacene class compound, class compound, two aromatic ethylene class compounds, triphenylamine ethylene compounds, amine chemical combination
Thing, carbazole compound, benzimidazoles compound, furfuran compound, metal organic fluorescence complex compound, metal Phosphorescent
Complex compound (such as Ir, Pt, Os, Cu), polyvinylcarbazole, poly-organosilicon compound, polythiophene organic polymer luminescent material, it
Can be used alone, can also a variety of mixtures use.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires good electronic transmission performance, energy
It is enough effectively electronics from cathode transport to luminescent layer in, there is very big electron mobility.Following compound can be selected, but
It is not limited to this：Oxa- oxazole, thiazole compound, triazole compound, three nitrogen piperazine class compounds, triazine class chemical combination
Thing, quinoline class compound, phenodiazine anthracene compound, siliceous heterocycle compound, quinolines, ferrosin class compound,
Metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzimidazoles compound.
Electronics, effectively can be injected into organic layer by the electron injecting layer of organic electroluminescence device of the present invention from cathode
In, it is mainly selected from the alkali metal either compound of alkali metal or compound or alkali selected from alkaline-earth metal or alkaline-earth metal
Metal complex, can select following compound, but not limited to this：Alkali metal, alkaline-earth metal, rare earth metal, alkali metal
Oxide either halide, the oxide of alkaline-earth metal or halide, the oxide of rare earth metal or halide, alkali metal
Or the organic complex of alkaline-earth metal；Preferably lithium, lithium fluoride, lithia, lithium nitride, 8-hydroxyquinoline lithium, caesium, carbonic acid
Caesium, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesia, these compounds can individually make
With can also mixture use, can also be used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in the organic electroluminescence device of the present invention, can be steamed by vacuum vapour deposition, molecular beam
It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.It can make for metal motor
Prepared with vapour deposition method or sputtering method.
Device experimental shows that luxuriant and rich with fragrance class compound of the present invention as described in structural formula I, there is preferable heat endurance, height to shine
Efficiency, high luminance purity, low driving voltage.The organic electroluminescence device made of the phenanthrene class compound has electroluminescent
Efficiency is good and excitation purity is excellent and the advantages of long lifespan.
Brief description of the drawings
Fig. 1 is a kind of organic electroluminescence device structure diagram of the present invention,
Wherein, 110 be glass substrate, and 120 be anode, and 130 be hole injection layer, and 140 be hole transmission layer, and 150 be hair
Photosphere, 160 be electron transfer layer, and 170 be electron injecting layer, and 180 be cathode.
Embodiment
In order to describe the present invention in more detail, especially exemplified by example below, but not limited to this.
Embodiment 1
The synthetic route of compound 1
The synthetic method of intermediate 1-1
In flask, N is added9, N10- diphenyl phenanthrene -9,10- diamines (10g, 28mmol), bromo- 9, the 9- dimethyl fluorenes of 2-
(8.3g, 30mmol), sodium tert-butoxide (3.1g, 42mmol), palladium (0.3g), X-phos (0.5g), toluene (100mL),
Nitrogen protection under be heated to reflux 10 it is small when, cooling, remove solvent, purify to obtain product 7.4g, yield 48% through column chromatography.
The synthetic method of compound 1
In flask, intermediate 1-1 (1.5g, 2.7mmol), 4- bromines dibenzofurans (0.66g, 2.7mmol), uncle are added
Sodium butoxide (0.3g, 4mmol), palladium (0.1g), X-phos (0.2g), toluene (15mL), is heated to reflux under nitrogen protection
10 it is small when, cooling, remove solvent, purify to obtain product 1.3g, yield 68% through column chromatography.
Embodiment 2
The synthetic route of compound 6
The synthetic method of intermediate 6-1
Synthetic method is as the synthesis of intermediate 1-1, and raw materials used is 4- bromines 9, two fluorenes of 9- spiral shells, yield 41%.
The synthetic method of compound 6
Synthetic method is as the synthesis of compound 1, and raw materials used is intermediate 6-1, yield 54%.
Embodiment 3
The synthetic route of compound 11
Synthetic method is as the synthesis of compound 1, and raw materials used is intermediate 1-1 and 2- bromine dibenzofurans, yield
For 57%.
Embodiment 4
The synthetic route of compound 19
Synthetic method is as the synthesis of compound 1, and raw materials used is intermediate 1-1 and 4- bromodiphenylthiophene, yield
For 63%.
Embodiment 5
The synthetic route of compound 26
The synthetic method of intermediate 26-1
Synthetic method is as with intermediate 1-1, and raw materials used is 9,9- diphenyl -2- bromine fluorenes, yield 38%.
The synthetic method of compound 26
Synthetic method is as with compound 1, and raw materials used is intermediate 26-1 and 2- bromodiphenylthiophene, and yield is
49%.
Embodiment 6-10
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment
First, by electrically conducting transparent ito glass substrate 110 (carrying anode 120 above) (the limited public affairs of South China glass group share
Department) pass through successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, on ITO spin coating 45nm thickness PEDOT:PSS (Polyglycolic acid fibre-poly- (styrene sulfonate)) is
It is 30 minutes dry at 130,150 DEG C of hole injection layer.
Then, the compounds of this invention of 40nm thickness is deposited on hole injection layer as hole mobile material 140.
Then, the luminescent layer 150 of 30nm thickness is deposited on electronic barrier layer, wherein, the compounds of this invention shines for main body
Material, and using weight ratio as 8% Ir (ppy)3Guest materials is adulterated as phosphorescence.
Then, the TMPYPB of 40nm thickness is deposited on the light-emitting layer as electron transfer layer 160.
Finally, evaporation 1nm LiF are electron injecting layer 170 and 80nm Al as device cathodes 180.
Prepared device (structure diagram is shown in Fig. 1) with Photo Research PR650 spectrometers measure
100mA/cm2Current density under external quantum efficiency be such as table 1.
Comparative example 1
Comparative example 1 prepares the method for device as the preparation method of embodiment 6-10, except replacing the present inventionization with HT1
Compound as hole mobile material outside.
Table 1
| Embodiment | Compound | Current efficiency (100%) | Glow color |
| 6 | 1 | 9.4 | Green light |
| 7 | 6 | 8.9 | Green light |
| 8 | 11 | 9.1 | Green light |
| 9 | 19 | 8.6 | Green light |
| 10 | 26 | 8.7 | Green light |
| Comparative example 1 | HT1 | 6.3 | Green light |
The structural formula of compound described in device is as follows：
As it can be seen from table 1 the luxuriant and rich with fragrance class compound of the present invention is used for organic electroluminescence device, work electricity can be reduced
The advantages that pressure, improves device efficiency, and the organic electroluminescence device of preparation has high efficiency and optical purity, and service life is long.
Preferred embodiment of the invention described in detail above.It should be appreciated that those of ordinary skill in the art without
Need creative work to conceive according to the present invention and make many modifications and variations.Therefore, all technologies in the art
Personnel are available by logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea
Technical solution, all should be in the protection domain being defined in the patent claims.
Claims (10)
1. a kind of phenanthrene class compound, it is characterised in that be the compound with following structural formula I：
Wherein Ar1And Ar2Independently selected from substitution or the aryl of unsubstituted C6-C30；
R1And R2Independently selected from the aryl of the alkyl of C1-C12, substitution or unsubstituted C6-C30；
A is selected from O, S or Se.
2. phenanthrene class compound as claimed in claim 1, it is characterised in that Ar1And Ar2Independently selected from phenyl, naphthyl, biphenyl
Base, three and phenyl, anthryl, phenanthryl, pyrenyl, base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (9,9- bis- substitutes or unsubstituted
Aryl) fluorenyl, 9,9- be Spirofluorene-based, substitution either unsubstituted dibenzothiophene, substitution or unsubstituted dibenzo furan
Mutter base, above aryl can also further substitute for the alkyl of C1-C12.
3. phenanthrene class compound as claimed in claim 1, it is characterised in that R1And R2Independently selected from hydrogen, methyl, ethyl, third
Base, isopropyl, butyl, phenyl, aminomethyl phenyl or xenyl.
4. phenanthrene class compound as claimed in claim 1, it is characterised in that be the compound of following structural 1-36：
5. application of the luxuriant and rich with fragrance class compound in organic electroluminescence device described in claim 1.
6. a kind of organic electroluminescence device, which includes anode, cathode and organic layer, and organic layer includes luminescent layer, hole
At least one layer in implanted layer, hole transmission layer, exciton barrier-layer, electron transfer layer, it is characterised in that in the organic layer extremely
Few one layer contains luxuriant and rich with fragrance class compound as claimed in claim 1.
7. organic electroluminescence device as claimed in claim 6, it is characterised in that the luxuriant and rich with fragrance class compound as described in structural formula I
The organic layer at place is hole transmission layer.
8. organic electroluminescence device as claimed in claim 6, it is characterised in that the luxuriant and rich with fragrance class compound as described in structural formula I
A kind of compound therein is used alone, or uses two or more the compound in structural formula I at the same time.
9. organic electroluminescence device as claimed in claim 6, it is characterised in that contain such as right in the hole transmission layer
It is required that the compound of one or more kinds of structural formula 1-36 described in 4.
10. organic electroluminescence device as claimed in claim 6, it is characterised in that the gross thickness of the organic layer is 1-
1000nm。
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| CN201711318031.1A CN108003121A (en) | 2017-12-12 | 2017-12-12 | A kind of phenanthrene class compound and application thereof and organic electroluminescence device |
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| CN201711318031.1A CN108003121A (en) | 2017-12-12 | 2017-12-12 | A kind of phenanthrene class compound and application thereof and organic electroluminescence device |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110627666A (en) * | 2019-09-12 | 2019-12-31 | 中国科学院化学研究所 | Fluorenyl tetramine pyrene hole transport material and application thereof in perovskite solar cell |
| WO2021206504A1 (en) * | 2020-04-09 | 2021-10-14 | 주식회사 엘지화학 | Organic light-emitting device |
| KR20210125939A (en) * | 2020-04-09 | 2021-10-19 | 주식회사 엘지화학 | Organic light emitting device |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110266526A1 (en) * | 2010-04-28 | 2011-11-03 | Universal Display Corporation | Triphenylene-Benzofuran/Benzothiophene/Benzoselenophene Compounds With Substituents Joining To Form Fused Rings |
| US20130234118A1 (en) * | 2012-03-06 | 2013-09-12 | Samsung Display Co. Ltd. | Amine-based compound, organic light-emitting diode including the same, and organic light-emitting apparatus including the amine-based compound |
| CN105669466A (en) * | 2016-03-16 | 2016-06-15 | 上海道亦化工科技有限公司 | Compound based on fluoranthene and organic electroluminescence device |
-
2017
- 2017-12-12 CN CN201711318031.1A patent/CN108003121A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110266526A1 (en) * | 2010-04-28 | 2011-11-03 | Universal Display Corporation | Triphenylene-Benzofuran/Benzothiophene/Benzoselenophene Compounds With Substituents Joining To Form Fused Rings |
| US20130234118A1 (en) * | 2012-03-06 | 2013-09-12 | Samsung Display Co. Ltd. | Amine-based compound, organic light-emitting diode including the same, and organic light-emitting apparatus including the amine-based compound |
| CN105669466A (en) * | 2016-03-16 | 2016-06-15 | 上海道亦化工科技有限公司 | Compound based on fluoranthene and organic electroluminescence device |
Non-Patent Citations (1)
| Title |
|---|
| 黄锦海: "基于蒽的有机电致发光材料的合成和性能研究", 《华东理工大学博士学位论文》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110627666A (en) * | 2019-09-12 | 2019-12-31 | 中国科学院化学研究所 | Fluorenyl tetramine pyrene hole transport material and application thereof in perovskite solar cell |
| WO2021206504A1 (en) * | 2020-04-09 | 2021-10-14 | 주식회사 엘지화학 | Organic light-emitting device |
| KR20210125939A (en) * | 2020-04-09 | 2021-10-19 | 주식회사 엘지화학 | Organic light emitting device |
| CN114144901A (en) * | 2020-04-09 | 2022-03-04 | 株式会社Lg化学 | Organic light emitting device |
| KR102573176B1 (en) | 2020-04-09 | 2023-09-04 | 주식회사 엘지화학 | Organic light emitting device |
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Application publication date: 20180508 |