CN105601612A - Phosphorescence main body compound containing indole groups and organic electroluminescent device of phosphorescence main body compound - Google Patents
Phosphorescence main body compound containing indole groups and organic electroluminescent device of phosphorescence main body compound Download PDFInfo
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Abstract
The invention provides a phosphorescence main body compound containing indole groups. The compound has better thermal stability, high luminous efficiency and high luminous purity, can be used for manufacturing organic electroluminescent devices, and is applied to the fields of organic solar batteries, organic thin film transistors or organic photoreceptors. The invention also provides an organic electroluminescent device, which comprises an anode, a cathode and an organic layer, wherein the organic layer comprises one layer or more than one layer in a luminous layer, a hole injection layer, a hole transmission layer, a hole blocking layer, an electron injection layer and an electron transmission layer; at least one layer in the organic layer comprises the compound shown as the structural formula I. The structural formula I is shown as the accompanying drawing.
Description
Technical field
The present invention relates to field of organic electroluminescent materials, be specifically related to a kind of phosphorescence main body chemical combination that contains indolyl radicalThing and organic electroluminescence device thereof, belong to organic electroluminescence device Display Technique field.
Background technology
Organic electroluminescence device (OLEDs) is by spin coating or vacuum evaporation deposition one between two metal electrodesThe device that layer organic material is prepared from, three layers of classical organic electroluminescence device comprise hole transmission layer, luminescent layerAnd electron transfer layer. The hole being produced by anode follows the electronics being produced by negative electrode to be combined in through electron transfer layer through hole transmission layerLuminescent layer forms exciton, then luminous. Organic electroluminescence device can be adjusted by the material that changes luminescent layer as requiredThe light of the various needs of joint transmitting.
Organic electroluminescence device, as a kind of novel Display Technique, has self-luminous, wide visual angle, low energy consumption, efficiencyHigh, thin, rich color, fast response time, Applicable temperature scope are wide, low driving voltage, can make flexible and transparentThe particular advantages such as display floater and environmental friendliness, can be applied in flat-panel monitor and a new generation's illumination is upper, also can be used asThe backlight of LCD.
Since invention at the bottom of the eighties in 20th century, organic electroluminescence device is industrially application to some extent, such asThe factors such as the screen such as camera and mobile phone, but current OLED device is because efficiency is low, and service life is short restrict that it is widerGeneral application, particularly large screen display, therefore need to improve the efficiency of device. And just restrict one of them key factorIt is the performance of the electroluminescent organic material in organic electroluminescence device. In addition due to OLED device apply voltage-operatedTime, can produce Joule heat, make organic material that crystallization easily occur, affect life-span and the efficiency of device, therefore, also needThe electroluminescent organic material of exploitation stability and high efficiency.
Organic electrophosphorescenpolymer phenomenon, has broken through organic electroluminescent quantum efficiency and has limited lower than 25% theory, rises to100% (BaldoM.A., ForrestS.R.Etal, Nature, 1998,395,151-154), its application is also carried widelyThe high efficiency of organic electroluminescence device. Usually, electroluminescent phosphorescence need to adopt host-guest system technology, conventional as phosphorusThe CBP (4,4'-bis (9-carbazolyl)-biphenyl) of light material of main part has efficient and high triplet, when its workDuring for material of main part, triplet energy state can be transferred to object phosphorescent light-emitting materials from luminous material of main part effectively. But byEasily transmit and the difficult mobile characteristic of electronics in hole in CBP, makes the charge unbalance of luminescent layer, and result has reduced the effect of deviceRate.
Summary of the invention
First the present invention provides a kind of phosphorescence host compound that contains indolyl radical, and it is to have following structural formula I'sCompound:
Wherein, L is sky or phenyl ring;
Z1-Z3Wherein have one at least for N, remaining is CH;
Ar1And Ar2Respectively independently selected from the aromatic rings of C6-C30.
Preferably, Ar1And Ar2Respectively independently selected from phenyl, xenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, fluorantheneBase, (9,9-dialkyl group) fluorenyl, (9,9-bis-replaces or unsubstituted aryl) fluorenyl, 9,9-is Spirofluorene-based, replace or do not getDibenzothiophenes base, replacement or the unsubstituted dibenzofuran group in generation; Wherein aforesaid aromatic ring can be further by C1-C4'sAlkyl replaces.
Further preferably, the phosphorescence host compound that contains indolyl radical described in is the chemical combination of following structural 1-38Thing:
The phosphorescence host compound that contains indolyl radical of the present invention can be applied in organic electroluminescence device, You JitaiSun energy battery, OTFT or organophotoreceptorswith field.
The present invention also provides a kind of organic electroluminescence device, and this device comprises anode, negative electrode and organic layer, organic layerComprise the one deck or in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layerMore than layer, in wherein said organic layer, have at least one deck to contain just like the phosphorescence subject highlighting that contains indolyl radical described in structural formula ICompound:
Wherein L, Ar1、Ar2And Z1-Z3Definition as previously mentioned.
Wherein organic layer is luminescent layer;
Or organic layer is luminescent layer and electron transfer layer;
Or organic layer is luminescent layer, electron transfer layer and electron injecting layer;
Or organic layer is hole transmission layer and luminescent layer;
Or organic layer is hole injection layer, hole transmission layer and luminescent layer;
Or organic layer is hole transmission layer, luminescent layer and electron transfer 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; OrOrganic layer is hole injection layer, hole transmission layer, barrier layer, luminescent layer, electron transfer layer and electron injecting layer;
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer;
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and hole blocking layer.
Preferably, the phosphorescence host compound place layer that contains indolyl radical as described in structural formula I is luminescent layer.
Preferably, the phosphorescence host compound that contains indolyl radical as described in structural formula I is the chemical combination of structural formula 1-38Thing.
When the phosphorescence host compound that contains indolyl radical as described in structural formula I is prepared for luminescent device, Ke YidanSolely use, also can use with other compound; The phosphorescence host compound that contains indolyl radical as described in structural formula ICan use separately a kind of compound wherein, also can use two or more the compound in structural formula I simultaneously.
Organic electroluminescence device of the present invention, further preferred mode is that this organic electroluminescence device comprises sunThe utmost point, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, wherein contain in luminescent layerThe compound of one or more structural formula I; Further preferably, in luminescent layer, contain one or more structureThe compound of formula 1-38.
The luminescent layer of organic electroluminescence device contains the luminous guest materials of phosphorescence and has the compound conduct of structural formula IMaterial of main part, wherein structural formula I compound is as material of main part, and its content is the 20-99.9% of whole luminescent layer weight, preferably80-99%, more preferably 90-99%.
The gross thickness of organic electroluminescence device organic layer of the present invention is 1-1000nm, preferably 50-500nm.
Organic electroluminescence device of the present invention, in the time using the present invention to have the compound of structural formula I, can be arranged in pairs or groups and makeWith other materials, as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layerDeng, and obtain blue light, green glow, gold-tinted, ruddiness or white light.
The hole transmission layer of organic electroluminescence device of the present invention and hole injection layer, material requested has good holeTransmission performance, can be transferred to hole luminescent layer from anode effectively. Can comprise that other little molecule and macromolecule are organicCompound, includes but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanineCompounds, the assorted triphen (hexanitrilehexaazatriphenylene), 2,3,5 of six cyano group six, 6-tetrafluoro-7,7', 8,8'-tetra-cyanogen dimethyl 1,4-benzoquinone (F4-TCNQ), PVK, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of organic electroluminescence device of the present invention, has the good characteristics of luminescence, can regulate as requiredThe scope of visible ray. There is structural formula I compound as phosphorescent light body material, other phosphorescence of can also arranging in pairs or groups except of the present inventionMaterial of main part, the luminous guest materials of phosphorescence can comprise at least one metal being selected from ruthenium, copper, rhodium, silver, iridium, platinum, gold and osmiumMetal-organic complex.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires to have good electronic transmission performance, energyEnough effectively during electronics is from cathode transport to luminescent layer, there is very large electron mobility. Can select following compound, butTo be not limited to this: oxa-oxazole, thiazole compound, triazole compound, three nitrogen piperazine compounds, triazine class chemical combinationThing, quinoline compounds, phenazine compounds, siliceous heterocycle compound, quinolines, ferrosin compounds,Metallo-chelate is (as Alq3), fluorine substituted benzene compound, benzimidazoles compound.
The electron injecting layer of organic electroluminescence device of the present invention, can be injected into organic layer electronics from negative electrode effectivelyIn, be mainly selected from alkali metal or alkali-metal compound, or be selected from compound or the alkali of alkaline-earth metal or alkaline-earth metalMetal complex, can select following compound, but is not limited to this: alkali metal, alkaline-earth metal, rare earth metal, alkali-metalThe oxide of the oxide of oxide or halide, alkaline-earth metal or halide, rare earth metal or halide, alkali metalOr the organic complex of alkaline-earth metal; Be preferably lithium, lithium fluoride, lithia, lithium nitride, oxine lithium, caesium, carbonic acidCaesium, oxine caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesia, these compounds can make separatelyWith also can using by mixture, also can be used in conjunction with other electroluminescent organic materials.
Every one deck of organic layer in organic electroluminescence device of the present invention, can pass through vacuum vapour deposition, molecular beam steamingPrepared by the modes such as plating method, the dip coating that is dissolved in solvent, spin-coating method, excellent painting method or inkjet printing. Can make for metal motorBe prepared with vapour deposition method or sputtering method.
Device experimental shows, the aromatic amine compounds of the present invention as described in structural formula I, has better heat endurance, heightLuminous efficiency, high luminance purity. The organic electroluminescence device that adopts this aromatic amine compounds to make has electroluminescent effectThe advantage that the good and excitation excellence of rate and life-span are grown.
Brief description of the drawings
Fig. 1 is a kind of organic electroluminescence device structural representation of the present invention;
Wherein, 110 are represented as glass substrate, and 120 are represented as anode, and 130 are represented as hole injection layer, 140 hole transportLayer, 150 are represented as barrier layer, and 160 are represented as luminescent layer, and 170 are represented as electron transfer layer, and 180 are represented as electron injecting layer,190 are represented as negative electrode.
Detailed description of the invention
In order more to describe the present invention in detail, especially exemplified by following example, but be not limited to this.
Embodiment 1
Synthesizing of compound 2
Intermediate 2-1's is synthetic
In the single port flask of 500mL, add successively 5-bromo indole (20.00g, 0.1mol), connection boric acid pinacol ester(51.80g, 0.2mmol), potassium acetate (22.80g, 0.2mol), [two (diphenylphosphino) ferrocene of 1,1'-] palladium chloride(1.50g), 350mL dioxane, 8h refluxes under nitrogen protection. After cooling, revolve to steam and remove dioxane, use 200mL distilled waterAfter washing, use dichloromethane extraction 3 times. Be recrystallized and obtain product 21.8g with methyl alcohol-carrene, productive rate is 90%.
Intermediate 2-2's is synthetic
In the single port flask of 50mL, add successively intermediate 2-1 (2.4g, 10mmol), 9-phenyl-9-(4-bromophenyl)Fluorenes (4.4g, 11mmol), potash (2.7g, 20mmol), four triphenyl phosphorus palladiums (50mg), dioxane (20.0mL) and water(4.0mL), the 5h that refluxes under nitrogen protection. After cooling, revolve to steam and remove dioxane, with using dichloromethane after the washing of 20mL distilled waterAlkane extraction 3 times. Thick product obtains product 3.5g through column chromatography purification, and productive rate is 80%.
Synthesizing of compound 2
In there-necked flask, add intermediate 2-2 (2g, 4.6mmol), dimethyl formamide (30ml), then add hydrogenChange sodium (264mg, 6.9mmol), react 1 hour, then add 2-chloro-4,6-diphenyl pyrimidine (1.5g, 5.5mmol). Room temperature is anti-Should spend the night, be added to the water, filter, filter cake obtains product 2.5g with oxolane and ethyl alcohol recrystallization, productive rate 82%.
Embodiment 2
Synthesizing of compound 3
Synthetic method is the same with compound 2, and except chloro-4 with 2-, 6-diphenyl-s-triazine replaces 2-chloro-4,6-hexicholOutside yl pyrimidines, productive rate 85%.
Embodiment 3
Synthesizing of compound 18
In there-necked flask, add intermediate 2-2 (2g, 4.6mmol), 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-Triazine (1.8g, 4.6mmol), potash (1.2g, 9.2mmol), cuprous iodide (0.3g), Phen (0.3g) and nitrobenzene(30ml), add hot reflux 12 hours, cooling, removal of solvent under reduced pressure, thick product obtains productive rate 2.3g, productive rate through column chromatography purification68％。
Embodiment 4
Synthesizing of compound 22
Intermediate 22-1's is synthetic
Synthetic method is the same with intermediate 2-2's, and except bromo-9 with 2-, 9-diphenylfluorene is outside raw material, productive rate 86%.
Synthesizing of compound 22
Synthetic method is the same with compound 3, except replacing intermediate 2-2 with intermediate 22-1, and productive rate 75%.
Embodiment 5
Synthesizing of compound 27
Synthetic method is synthetic the same with compound 18, except replacing intermediate 2-2 with intermediate 22-1 and with 4-(4-Bromophenyl)-2,6-diphenyl pyridine replaces 2-(3-bromophenyl)-4, outside 6-diphenyl-1,3,5-triazines, productive rate 70%.
Embodiment 6
Synthesizing of compound 33
Intermediate 33-1's is synthetic
Synthetic method is the same with intermediate 2-2, and except bromo-9 with 4-, 9-diphenylfluorene is as outside raw material, productive rate 90%.
Synthesizing of compound 33
Synthetic method is synthetic the same with compound 3, except being raw material with intermediate 33-1, and productive rate 80%.
Embodiment 7
Synthesizing of compound 34
Synthetic method is synthetic the same with compound 3, and except chloro-4 with 2-, 6-bis-(4-biphenyl)-s-triazine replaces 2-4,Outside 6-diphenyl-s-triazine, productive rate 76%.
Embodiment 8-14
The preparation of organic electroluminescence device
Use the compound of embodiment to prepare OLED.
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (the limited public affairs of South China glass group shareDepartment) warp successively: deionized water, ethanol, acetone and deionized water are cleaned, then use oxygen plasma treatment 30 seconds.
Then, the thick MnO of evaporation 50nm on ITO3(molybdenum oxide) is hole injection layer 130.
Then the NPB that, evaporation 25nm is thick on hole injection layer is hole mobile material 140.
Then, evaporation TCTA, forms the thick electronic barrier layer 150 of 8nm.
Then the luminescent layer 160 that, evaporation 20nm is thick on electronic barrier layer. Wherein, the compounds of this invention is that main body is luminousMaterial, and with the Ir (ppy) of 9.8% weight ratio2Acac is as the phosphorescence guest materials that adulterates.
Then the TPBi that, evaporation 40nm is thick on luminescent layer is as electron transfer layer 170.
Finally, evaporation 1nmLiF is that electron injecting layer 180 and 80nmAl are as device cathodes 190.
Prepared device (structural representation is shown in Fig. 1) record with PhotoResearchPR650 spectrometer200mA/cm2Brightness under efficiency be as table 1.
Comparative example
Device prepared by comparative example is the same with the preparation method of embodiment 8-14, except replacing the compounds of this invention with CBPOutside material of main part.
As can be seen from the above table, under identical current density condition, apply prepared by compound of the present invention organicThe efficiency of electroluminescent device is all higher than comparative example, and as mentioned above, compound of the present invention has high stability, the having of preparationOrganic electroluminescence devices has high efficiency and optical purity.
The structural formula of compound described in device is as follows:
More than describe preferred embodiment of the present invention in detail. Should be appreciated that those of ordinary skill in the art withoutNeed creative work just can design according to the present invention make many modifications and variations. Therefore, all technology in the artPersonnel are available by logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's ideaTechnical scheme, all should be in by the determined protection domain of claims.
Claims (10)
1. contain a phosphorescence host compound for indolyl radical, it is characterized in that it is the compound with following structural formula I:
Wherein, L is sky or phenyl ring;
Z1-Z3Wherein have one at least for N, remaining is CH;
Ar1And Ar2Respectively independently selected from the aromatic rings of C6-C30.
2. the phosphorescence host compound that contains indolyl radical according to claim 1, is characterized in that Ar1And Ar2Respectively solelyOn the spot be selected from phenyl, xenyl, naphthyl, anthryl, phenanthryl, pyrenyl, perylene base, fluoranthene base, (9,9-dialkyl group) fluorenyl, (9,9-bis-Replace or unsubstituted aryl) fluorenyl, 9,9-is Spirofluorene-based, replacement or unsubstituted dibenzothiophenes base, replacement or notThe dibenzofuran group replacing; Or aforesaid aromatic ring is further replaced by the alkyl of C1-C4.
3. the phosphorescence host compound that contains indolyl radical according to claim 1, is characterized in that it is lower array structureThe compound of formula 1-38:
。
4. an organic electroluminescence device, it comprises anode, negative electrode and organic layer, organic layer comprises luminescent layer, hole is injectedOne or more layers in layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, is characterized in that havingIn machine layer, at least one deck includes the phosphorescence host compound that contains indolyl radical as claimed in claim 1.
5. organic electroluminescence device according to claim 4, is characterized in that the indyl that contains as described in structural formula IThe phosphorescence host compound place layer of group is luminescent layer.
6. organic electroluminescence device according to claim 4, is characterized in that the indyl that contains as described in structural formula IThe phosphorescence host compound of group is the compound of structural formula 1-38.
7. organic electroluminescence device according to claim 4, is characterized in that the indyl that contains as described in structural formula IThe phosphorescence host compound of group uses separately, or and other compound uses.
8. organic electroluminescence device according to claim 4, is characterized in that the indyl that contains as described in structural formula IThe phosphorescence host compound of group uses separately a kind of compound wherein, or use simultaneously in structural formula I two kinds or two kinds withOn compound.
9. organic electroluminescence device according to claim 4, is characterized in that it comprises anode, hole injection layer, skyCave transport layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, is characterized in that containing in luminescent layer one or oneThe compound of above structural formula I.
10. organic electroluminescence device according to claim 4, is characterized in that it comprises anode, hole injection layer, skyCave transport layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, is characterized in that the compound containing in luminescent layer isThe compound of structural formula 1-38.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107129471A (en) * | 2016-02-26 | 2017-09-05 | 三星Sdi株式会社 | Organic compound, organic photoelectric device and display device |
| CN110168048A (en) * | 2017-01-05 | 2019-08-23 | 三星Sdi株式会社 | For the compound of organic photoelectric device, for the constituent of organic photoelectric device and display device |
| WO2019191454A1 (en) * | 2018-03-28 | 2019-10-03 | Kyulux, Inc. | Composition of matter for use organic light-emitting diodes |
| WO2021125813A1 (en) * | 2019-12-20 | 2021-06-24 | 주식회사 엘지화학 | Compound and organic light-emitting device comprising same |
| US11264574B2 (en) | 2016-07-29 | 2022-03-01 | Samsung Sdi Co., Ltd. | Composition for organic optoelectronic element, organic optoelectronic element, and display device |
| US11678572B2 (en) | 2016-06-29 | 2023-06-13 | Samsung Sdi Co., Ltd. | Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display apparatus |
| US11706975B2 (en) | 2016-06-29 | 2023-07-18 | Samsung Sdi Co., Ltd. | Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display apparatus |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150106668A (en) * | 2014-03-12 | 2015-09-22 | (주)피엔에이치테크 | Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same |
| KR20150110101A (en) * | 2014-03-24 | 2015-10-02 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
| KR20150111441A (en) * | 2014-03-24 | 2015-10-06 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
-
2015
- 2015-12-29 CN CN201511005618.8A patent/CN105601612B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150106668A (en) * | 2014-03-12 | 2015-09-22 | (주)피엔에이치테크 | Novel compound for organic electroluminescent device and organic electroluminescent device comprising the same |
| KR20150110101A (en) * | 2014-03-24 | 2015-10-02 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
| KR20150111441A (en) * | 2014-03-24 | 2015-10-06 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107129471A (en) * | 2016-02-26 | 2017-09-05 | 三星Sdi株式会社 | Organic compound, organic photoelectric device and display device |
| US10516113B2 (en) | 2016-02-26 | 2019-12-24 | Samsung Sdi Co., Ltd. | Organic compound, organic optoelectric device and display device |
| CN107129471B (en) * | 2016-02-26 | 2021-05-07 | 三星Sdi株式会社 | Organic compound, organic photoelectric device and display device |
| US11678572B2 (en) | 2016-06-29 | 2023-06-13 | Samsung Sdi Co., Ltd. | Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display apparatus |
| US11706975B2 (en) | 2016-06-29 | 2023-07-18 | Samsung Sdi Co., Ltd. | Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display apparatus |
| US11264574B2 (en) | 2016-07-29 | 2022-03-01 | Samsung Sdi Co., Ltd. | Composition for organic optoelectronic element, organic optoelectronic element, and display device |
| CN110168048A (en) * | 2017-01-05 | 2019-08-23 | 三星Sdi株式会社 | For the compound of organic photoelectric device, for the constituent of organic photoelectric device and display device |
| CN110168048B (en) * | 2017-01-05 | 2022-10-21 | 三星Sdi株式会社 | Organic photoelectric device, compound and composition used for same, and display device |
| WO2019191454A1 (en) * | 2018-03-28 | 2019-10-03 | Kyulux, Inc. | Composition of matter for use organic light-emitting diodes |
| WO2021125813A1 (en) * | 2019-12-20 | 2021-06-24 | 주식회사 엘지화학 | Compound and organic light-emitting device comprising same |
| KR20210080231A (en) * | 2019-12-20 | 2021-06-30 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
| KR102511678B1 (en) | 2019-12-20 | 2023-03-21 | 주식회사 엘지화학 | Compound and organic light emitting device comprising the same |
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