CN105153130A - Electron transport compound adopting triazine derivative and OLED (organic light-emitting device) applying electron transport compound - Google Patents

Electron transport compound adopting triazine derivative and OLED (organic light-emitting device) applying electron transport compound Download PDF

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CN105153130A
CN105153130A CN201510481602.8A CN201510481602A CN105153130A CN 105153130 A CN105153130 A CN 105153130A CN 201510481602 A CN201510481602 A CN 201510481602A CN 105153130 A CN105153130 A CN 105153130A
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triazine derivative
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黄锦海
苏建华
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Shanghai Taoe Chemical Technology Co Ltd
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Abstract

The invention provides an organic light-emitting compound adopting a triazine derivative shown in the structural formula I. The compound has better thermal stability, high luminous efficiency and high luminous purity, can be used for manufacturing OLEDs (organic light-emitting devices) and can be applied to the fields of organic solar cells, organic thin-film transistors or organic photoreceptors. The invention further provides an OLED which comprises an anode, a cathode and an organic layer, wherein the organic layer comprises one or more of a luminous layer, a hole injection layer, a hole transporting layer, a hole blocking layer, an electron injection layer and an electron transporting layer, and at least one layer in the organic layer contains the compound shown in the structural formula I.

Description

Triazine derivative electric transmission compound and organic electroluminescence device thereof
Technical field
The present invention relates to field of organic electroluminescent materials, be specifically related to a kind of organic electroluminescent compounds and organic electroluminescence device thereof of triazine derivative, belong to organic electroluminescence device technique of display field.
Background technology
Organic electroluminescence device (OLEDs) is deposit by spin coating or vacuum evaporation the device that one deck organic materials is prepared between two metal electrodes, and classical three layers of organic electroluminescence device comprise hole transmission layer, luminescent layer and electron transfer layer.The hole produced by anode is followed through hole transmission layer the electronics produced by negative electrode to be combined in luminescent layer through electron transfer layer and is formed exciton, then luminous.Organic electroluminescence device can regulate by the material changing luminescent layer the light launching various needs as required.
Organic electroluminescence device is as a kind of novel technique of display, there is luminous, wide viewing angle, less energy-consumption, efficiency are high, thin, rich color, fast response time, Applicable temperature scope wide, low driving voltage, flexible and the particular advantages such as transparent display panel and environmental friendliness can be made, can be applied in flat-panel monitor and a new generation's illumination, also can as the backlight of LCD.
Since invention at the bottom of the eighties in 20th century, organic electroluminescence device is industrially applied to some extent, such as the screen such as camera and mobile phone, but current OLED due to efficiency low, the factors such as work-ing life is short restrict it and apply widely, particularly large screen display.And restrict the performance that one of them important factor is exactly the electroluminescent organic material in organic electroluminescence device.In addition because OLED is when applying voltage-operated, can joule heating be produced, make organic materials easily crystallization occur, have impact on life-span and the efficiency of device, therefore, also need the electroluminescent organic material developing stability and high efficiency.
In OLED material, because the speed of most electroluminescent organic material transporting holes is faster than the speed of transmission electronic, easily cause electronics and the number of cavities imbalance of luminescent layer, the efficiency of such device is just lower.Three (oxine) aluminium (Alq 3) since invention, be extensively studied, but it is still very low as its electronic mobility of electron transport material, and the intrinsiccharacteristic that self can degrade, with in the device of electron transfer layer, there will be the situation of voltage drop, simultaneously, due to lower electronic mobility, a large amount of holes is made to enter into Alq 3in layer, excessive hole with the form quantity of radiant energy of non-luminescent, and when as electron transport material, due to the characteristic of its green light, application is restricted.Therefore, development stability and have the electron transport material of larger electronic mobility, has great value to widely using of organic electroluminescence device.
Summary of the invention
First the present invention provides a kind of triazine derivative organic electroluminescent electric transmission formed material, and it is the compound with following structural formula I:
Wherein, R 1, R 2, R 3, R 4separately be selected from hydrogen, D atom, the alkyl of C1-C12, the alkoxyl group of C1-C8, the replacement of C6-C30 or unsubstituted aryl;
L is selected from singly-bound, the alkyl of C1-C6, the substituted or unsubstituted aryl of C6-C30, the replacement of C3-C30 or unsubstituted heteroaryl;
A is selected from O, S, Se, SO, SO 2.
Preferably, R 1, R 2, R 3, R 4separately be selected from C1-C8 alkyl, the replacement of C6-C30 or unsubstituted aryl;
L is selected from the substituted or unsubstituted aryl of singly-bound, C6-C30;
A is selected from O, S.
More preferably, R 1, R 2, R 3, R 4separately be selected from methyl, ethyl, propyl group, sec.-propyl, the tertiary butyl, normal-butyl, n-hexyl, phenyl, naphthyl, xenyl;
L is selected from singly-bound, phenyl ring, xenyl.
Further preferably, triazine derivative of the present invention is the compound of following structural 1-16:
The organic electroluminescent electron transport material of triazine derivative of the present invention can be applied in organic electroluminescence device, organic solar batteries, OTFT or organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, this device comprises anode, negative electrode and organic layer, it is one or more layers that organic layer comprises in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, has one deck at least containing, for example the organic electroluminescent electron transport material of the triazine derivative described in structural formula I in wherein said organic layer:
Wherein R 1-R 4, L, A definition as previously mentioned.
Wherein organic layer is luminescent layer and electron transfer layer;
Or organic layer is luminescent layer, hole injection layer, hole transmission layer and electron transfer layer;
Or organic layer is luminescent layer, hole injection layer, hole transmission layer, electron transfer layer and electron injecting layer; Or organic layer is luminescent layer, hole transmission layer, electron transfer layer and electron injecting layer;
Or organic layer is luminescent layer, hole transmission layer and electron injecting layer.
Preferably, the layer at the triazine derivative place wherein as described in structural formula I is electron transfer layer or electron injecting layer;
Preferably, the triazine derivative wherein described in structural formula I is the compound of structural formula 1-16;
When triazine derivative as described in structural formula I is prepared for luminescent device, can be used alone, also can use with other compound; Triazine derivative as described in structural formula I can be used alone 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, preferred mode is further, this organic electroluminescence device comprises anode, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, the compound wherein containing structural formula I in electron transfer layer or electron injecting layer; Further preferably, the compound contained in electron transfer layer or electron injecting layer is the compound of structural formula 1-16.
In organic electroluminescence device of the present invention, Compounds of structural formula I also doublely can do electron injecting layer as during electron transfer layer.
The total thickness of organic electroluminescence device organic layer of the present invention is 1-1000nm, preferred 50-500nm.
Organic electroluminescence device of the present invention is when using the present invention to have the compound of structural formula I, can to arrange in pairs or groups use other materials, as medium at hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer, 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 hole transport performance, can effectively hole be transferred to luminescent layer from anode.Comprise other small molecules and macromolecular organic compound, include but not limited to carbazole compound, triaromatic amine compound, benzidine compound, compound of fluorene class, phthalocyanine-like compound, six cyano group six mix triphen (hexanitrilehexaazatriphenylene), 2,3,5,6-tetra-fluoro-7,7', 8,8'-tetra-cyanogen dimethyl-parabenzoquinone (F4-TCNQ), Polyvinyl carbazole, 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 the scope of visible ray as required.Can containing, for example lower compound, include, but are not limited to naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance compounds, bend compounds, fluoranthene compounds, anthracene compounds, pentacene compounds, perylene compounds, two aromatic ethylene compounds, triphenylamine ethylene compounds, aminated compounds, carbazole compound, benzimidazoles compound, furfuran compound, metal organic fluorescence complex compound, metal Phosphorescent complex compound is (as Ir, Pt, Os, Cu, Au), polyvinyl carbazole, poly organic silicon compound, the organic polymer luminescent materials such as Polythiophene, they can be used alone, also can use by multiple mixture.
The Organic Electron Transport Material of organic electroluminescence device of the present invention requires to have good electronic transmission performance, effectively during electronics is from cathode transport to luminescent layer, can have very large electronic mobility.Have except Compounds of structural formula I except of the present invention, following compound can also be selected, but be not limited thereto: oxa-oxazole, thiazole compound, triazole compound, three nitrogen piperazine compounds, triazine compounds, quinoline compounds, phenazine compounds, siliceous heterocyclic compound, quinolines, phenanthroline compounds, metallo-chelate are (as Alq 3), fluorine substituted benzene compound, benzimidazoles compound.
The electron injecting layer of organic electroluminescence device of the present invention, can effectively electronics be injected into organic layer from negative electrode, have except Compounds of structural formula I except of the present invention, mainly be selected from basic metal or alkali-metal compound, or be selected from compound or the alkali metal complex of alkaline-earth metal or alkaline-earth metal, following compound can be selected, but be not limited thereto: basic metal, alkaline-earth metal, rare earth metal, alkali-metal oxide compound or halogenide, the oxide compound of alkaline-earth metal or halogenide, the oxide compound of rare earth metal or halogenide, the organic complex of basic metal or alkaline-earth metal, be preferably lithium, lithium fluoride, Lithium Oxide 98min, lithium nitride, oxine lithium, caesium, cesium carbonate, oxine caesium, calcium, Calcium Fluoride (Fluorspan), calcium oxide, magnesium, magnesium fluoride, magnesiumcarbonate, magnesium oxide, these compounds can be used alone also can mixture use, also can with other electroluminescent organic materials with the use of.
Every one deck of organic layer in organic electroluminescence device of the present invention, can be prepared by modes such as vacuum vapour deposition, molecular beam vapour deposition method, the dip coating being dissolved in solvent, spin-coating method, stick coating method or spray ink Printings.Vapour deposition method or sputtering method can be used to be prepared for metal motor.
Device experimental shows, the triazine derivative of the present invention as described in structural formula I has better thermostability, high-luminous-efficiency, high luminance purity.The device adopting this organic electroluminescent compounds to make has the advantage that electroluminescent efficiency is good and purity of color is excellent and the life-span is long.
Accompanying drawing explanation
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 transmission layer, and 140 are represented as luminescent layer, and 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as negative electrode.
Embodiment
In order to more describe the present invention in detail, especially exemplified by following example, but be not limited thereto.
Embodiment 1
The synthesis of compound 1
The synthesis of intermediate A
In there-necked flask, add bromo-9, the 9-dimethyl fluorenes (5.5g, 20mmol) of 2-, magnesium chips (0.86g, 36mmol), dry tetrahydrofuran (THF) 60ml and 3 iodine, reflux 1 hour.Under ice bath, this reaction solution is added drop-wise in the tetrahydrofuran solution being dissolved with equal trichlorine piperazine (1.8g, 10mmol), drip off, be heated to 50 degree and react 12 hours, cooling, slowly adds aqueous ammonium chloride solution, with dichloromethane extraction, use anhydrous sodium sulfate drying again, filter, concentrated, organic layer obtains 7.5g product through column chromatography purification, and productive rate is 75%.
The synthesis of compound 1
In there-necked flask, add intermediate A (1.5g, 3mmol), 4-diphenylene-oxide boric acid (0.84g; 4mmol), the tetrahydrofuran (THF) of salt of wormwood (0.82g, 6mmol), 20ml, the water of 10ml and four triphenyl phosphorus palladiums (50mg); under nitrogen protection, reflux 24 hours, cooling; with chloroform extraction; with anhydrous sodium sulfate drying, filter, concentrate and obtain crude product; crude product obtains 1.3g product through column chromatography purification, and productive rate is 68%.
Embodiment 2
The synthesis of compound 9
In there-necked flask, add intermediate A (1.5g, 3mmol), 4-dibenzothiophene boric acid (0.91g; 4mmol), the tetrahydrofuran (THF) of salt of wormwood (0.82g, 6mmol), 20ml, the water of 10ml and four triphenyl phosphorus palladiums (50mg), under nitrogen protection; reflux 24 hours; cooling, with chloroform extraction, with anhydrous sodium sulfate drying; filter; concentrate and obtain crude product, crude product obtains 1.1g product through column chromatography purification, and productive rate is 58%.
Embodiment 3
The synthesis of compound 13
In there-necked flask; add intermediate A (1.5g; 3mmol), 3-(4-dibenzothiophene)-phenylo boric acid (1.2g; 4mmol), salt of wormwood (0.82g; 6mmol), the tetrahydrofuran (THF) of 20ml, the water of 10ml and four triphenyl phosphorus palladiums (50mg); under nitrogen protection; reflux 24 hours; cooling, with chloroform extraction, with anhydrous sodium sulfate drying; filter; concentrate and obtain crude product, crude product obtains 1.0g product through column chromatography purification, and productive rate is 45%.
Embodiment 4
The preparation of organic electroluminescence device
The compound 1 of embodiment 1 is used to prepare OLED.
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (China Nanbo Group Co) warp successively: deionized water, ethanol, acetone and deionized water are cleaned, then use oxygen plasma treatment 30 seconds.
Then, at NPB, form the hole transmission layer 130 that 60nm is thick.
Then, on hole transmission layer, the thick Alq of 37.5nm is crossed in steaming 31%C545T is as luminescent layer 140 in doping.
Then, the compound 1 that evaporation 37.5nm is thick on luminescent layer and Liq are as electron transfer layer 150, and the ratio of compound 1 and Liq is 1:1.
Finally, evaporation 1nmLiF is that electron injecting layer 160 and 100nmAl are as device cathodes 170.
Prepared device (structural representation is shown in Fig. 1) records at 20mA/cm with PhotoResearchPR650 spectrograph 2current density under power efficiency be 6.9lm/W, transmitting green light.
Embodiment 5
Except electron transfer layer compound 9 replaces compound 1, other the same with embodiment 4.
Prepared device is at 20mA/cm 2current density under power efficiency be 7.1lm/W, transmitting green light.
Embodiment 6
Except electron transfer layer compound 13 replaces compound 1, other the same with embodiment 4.
Prepared device is at 20mA/cm 2current density under power efficiency be 6.7lm/W, transmitting green light.
Comparative example 1
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (China Nanbo Group Co) warp successively: deionized water, ethanol, acetone and deionized water are cleaned, then use oxygen plasma treatment 30 seconds.
Then, evaporation NPB, forms the hole transmission layer 130 that 60nm is thick.
Then, on hole transmission layer, the thick Alq of 37.5nm is crossed in steaming 31%C545T is as luminescent layer 140 in doping.
Then, the Alq that evaporation 37.5nm is thick on luminescent layer 3as electron transfer layer 150.
Finally, evaporation 1nmLiF is that electron injecting layer 160 and 100nmAl are as device cathodes 170.
Prepared device PhotoResearchPR650 spectrograph records at 20mA/cm 2current density under power efficiency be 5.0lm/W, transmitting green light.
At identical conditions, apply the efficiency of organic electroluminescence device prepared by organic electroluminescent electron transport material of the present invention higher than comparative example, as mentioned above, compound of the present invention has high stability, and organic electroluminescence device prepared by the present invention 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 the ordinary skill of this area just design according to the present invention can make many modifications and variations without the need to creative work.Therefore, all technician in the art, all should by the determined protection domain of claims under this invention's idea on the basis of existing technology by the available technical scheme of logical analysis, reasoning, or a limited experiment.

Claims (10)

1. a triazine derivative organic electroluminescent compounds, is characterized in that it is the compound with following structural formula I:
Wherein, R 1, R 2, R 3, R 4separately be selected from hydrogen, D atom, the alkyl of C1-C12, the alkoxyl group of C1-C8, the replacement of C6-C30 or unsubstituted aryl;
L is selected from singly-bound, the alkyl of C1-C6, the substituted or unsubstituted aryl of C6-C30, the replacement of C3-C30 or unsubstituted heteroaryl;
A is selected from O, S, Se, SO, SO 2.
2. triazine derivative organic electroluminescent compounds according to claim 1, is characterized in that
Wherein R 1, R 2, R 3, R 4separately be selected from C1-C8 alkyl, the replacement of C6-C30 or unsubstituted aryl;
L is selected from the substituted or unsubstituted aryl of singly-bound, C6-C30;
A is selected from O, S.
3. triazine derivative organic electroluminescent compounds according to claim 1, is characterized in that
Wherein, R 1, R 2, R 3, R 4separately be selected from methyl, ethyl, propyl group, sec.-propyl, the tertiary butyl, normal-butyl, n-hexyl, phenyl, naphthyl, xenyl;
L is selected from singly-bound, phenyl ring, xenyl.
4. triazine derivative organic electroluminescent compounds according to claim 1, is characterized in that it is the compound of following structural 1-16:
5. an organic electroluminescence device, it comprises anode, negative electrode and organic layer, it is one or more layers that organic layer comprises in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, it is characterized in that in organic layer, at least one deck includes triazine derivative as claimed in claim 1.
6. organic electroluminescence device according to claim 5, is characterized in that the layer at the triazine derivative place as described in structural formula I is electron transfer layer or electron injecting layer.
7. organic electroluminescence device according to claim 5, is characterized in that the triazine derivative as described in structural formula I is used alone, or and other compound use.
8. organic electroluminescence device according to claim 5, the triazine derivative that it is characterized in that as described in structural formula I is used alone a kind of compound wherein, or uses two or more the compound in structural formula I simultaneously.
9. organic electroluminescence device according to claim 5, it comprises anode, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, it is characterized in that the compound containing structural formula I in electron transfer layer and/or electron injecting layer.
10. organic electroluminescence device according to claim 5, it comprises anode, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, it is characterized in that the compound contained in electron transfer layer and/or electron injecting layer is the compound of structural formula 1-16.
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CN107068879A (en) * 2016-04-25 2017-08-18 中节能万润股份有限公司 A kind of organic electroluminescence device containing compound in triazine class and its application
CN107501302A (en) * 2017-08-11 2017-12-22 长春海谱润斯科技有限公司 A kind of 1,3,5 pyrrolotriazine derivatives and its application
CN107814775A (en) * 2016-09-12 2018-03-20 Cmdl有限公司 Fluorenyl pyrrolotriazine derivatives organic compound and the organic electroluminescence device for including it
WO2018128255A1 (en) * 2017-01-05 2018-07-12 삼성에스디아이 주식회사 Compound for organic optoelectronic element, composition for organic optoelectronic element, organic optoelectronic element, and display device
TWI659027B (en) * 2017-01-05 2019-05-11 南韓商三星Ｓｄｉ股份有限公司 Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display device including the same
EP3503240A1 (en) * 2017-12-21 2019-06-26 Novaled GmbH Organic semiconductor layer
CN111004219A (en) * 2019-12-26 2020-04-14 陕西莱特迈思光电材料有限公司 Compound, organic electroluminescent device, and display device
US11084806B2 (en) 2016-07-12 2021-08-10 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device, and display device
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 (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1789252A (en) * 2005-12-29 2006-06-21 中国科学院上海有机化学研究所 Novel blue light material-thiotrzinone-containing anthracene derivatives
CN1950479A (en) * 2004-04-29 2007-04-18 西巴特殊化学品控股有限公司 Electroluminescent device
CN103325950A (en) * 2012-03-22 2013-09-25 陶氏环球技术有限责任公司 Charge transport layers and films containing the same
WO2015000549A1 (en) * 2013-07-02 2015-01-08 Merck Patent Gmbh Materials for electronic devices
WO2015073343A1 (en) * 2013-11-12 2015-05-21 Dow Global Technologies Llc Compositions containing fluorene substituted triazine derived compounds, and electronic devices containing the same

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1950479A (en) * 2004-04-29 2007-04-18 西巴特殊化学品控股有限公司 Electroluminescent device
CN1789252A (en) * 2005-12-29 2006-06-21 中国科学院上海有机化学研究所 Novel blue light material-thiotrzinone-containing anthracene derivatives
CN103325950A (en) * 2012-03-22 2013-09-25 陶氏环球技术有限责任公司 Charge transport layers and films containing the same
WO2015000549A1 (en) * 2013-07-02 2015-01-08 Merck Patent Gmbh Materials for electronic devices
WO2015073343A1 (en) * 2013-11-12 2015-05-21 Dow Global Technologies Llc Compositions containing fluorene substituted triazine derived compounds, and electronic devices containing the same

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
于军胜，等: "《OLED显示基础及产业化》", 28 February 2015 *

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107068879A (en) * 2016-04-25 2017-08-18 中节能万润股份有限公司 A kind of organic electroluminescence device containing compound in triazine class and its application
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
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
US11084806B2 (en) 2016-07-12 2021-08-10 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device, and display device
US11264574B2 (en) 2016-07-29 2022-03-01 Samsung Sdi Co., Ltd. Composition for organic optoelectronic element, organic optoelectronic element, and display device
CN107814775B (en) * 2016-09-12 2020-10-20 Cmdl有限公司 Fluorenyl triazine derivative organic compound and organic electroluminescent device comprising same
CN107814775A (en) * 2016-09-12 2018-03-20 Cmdl有限公司 Fluorenyl pyrrolotriazine derivatives organic compound and the organic electroluminescence device for including it
US11158817B2 (en) 2017-01-05 2021-10-26 Samsung Sdi Co., Ltd. Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic 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
TWI659027B (en) * 2017-01-05 2019-05-11 南韓商三星Ｓｄｉ股份有限公司 Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display device including the same
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
WO2018128255A1 (en) * 2017-01-05 2018-07-12 삼성에스디아이 주식회사 Compound for organic optoelectronic element, composition for organic optoelectronic element, organic optoelectronic element, and display device
CN107501302A (en) * 2017-08-11 2017-12-22 长春海谱润斯科技有限公司 A kind of 1,3,5 pyrrolotriazine derivatives and its application
CN111630676A (en) * 2017-12-21 2020-09-04 诺瓦尔德股份有限公司 Organic semiconductor layer
WO2019121664A1 (en) 2017-12-21 2019-06-27 Novaled Gmbh Organic semiconductor layer
EP3503240A1 (en) * 2017-12-21 2019-06-26 Novaled GmbH Organic semiconductor layer
CN111004219A (en) * 2019-12-26 2020-04-14 陕西莱特迈思光电材料有限公司 Compound, organic electroluminescent device, and display device

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