CN104178120A - Blue light phosphorescent host material containing benzimidazole unit, preparation method and organic electroluminescent device thereof - Google Patents
Blue light phosphorescent host material containing benzimidazole unit, preparation method and organic electroluminescent device thereof Download PDFInfo
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- CN104178120A CN104178120A CN201310204143.XA CN201310204143A CN104178120A CN 104178120 A CN104178120 A CN 104178120A CN 201310204143 A CN201310204143 A CN 201310204143A CN 104178120 A CN104178120 A CN 104178120A
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- ZHMKOSWPOJFQTD-UHFFFAOYSA-N C(C1)CC=CC1C(c1c2)(c3cc(-c4cccc(-c5nc6ccccc6[n]5-c5ccccc5)c4)ccc3-c1ccc2-c1cc(-c2nc(cccc3)c3[n]2-c2ccccc2)ccc1)c(cc1)cc(c2c3cccc2)c1[n]3-c1ccccc1 Chemical compound C(C1)CC=CC1C(c1c2)(c3cc(-c4cccc(-c5nc6ccccc6[n]5-c5ccccc5)c4)ccc3-c1ccc2-c1cc(-c2nc(cccc3)c3[n]2-c2ccccc2)ccc1)c(cc1)cc(c2c3cccc2)c1[n]3-c1ccccc1 ZHMKOSWPOJFQTD-UHFFFAOYSA-N 0.000 description 1
- GFFMIXGEYYHLRJ-UHFFFAOYSA-N C(C12)C=CC=C1N=C(c1cc(-c(cc3C4(c5ccccc5)c(cc5c6ccccc66)ccc5[n]6-c5ccccc5)ccc3-c(cc3)c4cc3-c3cc(-c4nc5ccccc5[n]4-c4ccccc4)ccc3)ccc1)N2c1ccccc1 Chemical compound C(C12)C=CC=C1N=C(c1cc(-c(cc3C4(c5ccccc5)c(cc5c6ccccc66)ccc5[n]6-c5ccccc5)ccc3-c(cc3)c4cc3-c3cc(-c4nc5ccccc5[n]4-c4ccccc4)ccc3)ccc1)N2c1ccccc1 GFFMIXGEYYHLRJ-UHFFFAOYSA-N 0.000 description 1
- GOESLOMYCNITBY-UHFFFAOYSA-N CC(C1)(C1(C)OSc1cccc(C2=NC3=CC=CCC3(C)N2c2ccccc2)c1)O Chemical compound CC(C1)(C1(C)OSc1cccc(C2=NC3=CC=CCC3(C)N2c2ccccc2)c1)O GOESLOMYCNITBY-UHFFFAOYSA-N 0.000 description 1
- FVXPNEZXAJEADX-UHFFFAOYSA-N Cc(cc1C(c2c3)(c4ccccc4)c(cc4)cc(c5ccccc55)c4[n]5-c4ccccc4)ccc1-c2ccc3Br Chemical compound Cc(cc1C(c2c3)(c4ccccc4)c(cc4)cc(c5ccccc55)c4[n]5-c4ccccc4)ccc1-c2ccc3Br FVXPNEZXAJEADX-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention belongs to the field of organic semiconductor materials, the invention discloses a blue light phosphorescent host material containing a benzimidazole unit, a preparation method and an organic electroluminescent device thereof. Specifically, the host material has a structural formula shown as the specification. The blue light phosphorescent host material containing the benzimidazole unit provided by the invention has a high triplet state energy level, and can effectively prevent back transmission of energy to the host material in a luminescence process, thus greatly improving the luminescence efficiency.
Description
Technical field
The present invention relates to organic semiconductor material field, relate in particular to a kind of blue emitting phosphor material of main part containing benzoglyoxaline unit and preparation method thereof.The invention still further relates to a kind of organic electroluminescence device, its luminescent layer material includes the blue emitting phosphor material of main part containing benzoglyoxaline unit.
Background technology
Organic electroluminescence device has that driving voltage is low, fast response time, angular field of view is wide and can be finely tuned and be changed luminescent properties and make rich color by chemical structure, easily realize the advantages such as resolving power is high, lightweight, large-area flat-plate demonstration, be described as " 21 century flat panel display ", become the focus of the subjects such as material, information, physics and flat pannel display area research.Following commercialization Organic Light Emitting Diode efficiently will contain organo-metallic phosphorescent substance possibly, because they can all catch singlet and triplet excitons, thereby realize 100% internal quantum efficiency.Yet, because the excited state exciton life-span of transition metal complex is relatively long, cause unwanted triplet state-triplet state (T
1-T
1) cancellation in device real work.In order to overcome this problem, investigators are often doped to triplet state shiner in organic main body material.
In recent years, green and red phosphorescent OLED device exhibits goes out gratifying electroluminescent efficiency.And efficient blue phosphorescent device seldom, major cause is to lack to have good carrier transmission performance and higher triplet (E simultaneously
t) material of main part.
Summary of the invention
One of problem to be solved by this invention is to provide a kind of have good carrier transmission performance and higher triplet (E
t) containing the blue emitting phosphor material of main part of benzoglyoxaline unit.
Two of problem to be solved by this invention is to provide a kind of preparation method of the blue emitting phosphor material of main part containing benzoglyoxaline unit.
Three of problem to be solved by this invention is to provide a kind of organic electroluminescence device, and its luminescent layer material includes the blue emitting phosphor material of main part containing benzoglyoxaline unit.
Technical scheme of the present invention is as follows:
Containing a blue emitting phosphor material of main part for benzoglyoxaline unit, its structural formula is as follows:
that is, 3-(3-(9,9'-spiral shell, two fluorenes-2-yl) phenyl)-5-(3-(9,9'-spiral shell, two fluorenes-7-yl) benzene)-4-phenyl-4H-1,2,4-triazole.
The preparation method of the above-mentioned blue emitting phosphor material of main part containing benzoglyoxaline unit, comprises the steps:
The compd A and the B that provide respectively following structural formula to represent,
it is 3-(the bromo-9-phenyl-9H-of 2,7-bis-fluorenes-9-yl)-9-phenyl-9H-carbazole;
it is 1-phenyl-2-(3-tetramethyl ethylene ketone boric acid ester phenyl)-1H-benzo [d] imidazoles;
Under oxygen-free environment, the compd A that is 1:2~2.4 by mol ratio and B are added in the organic solvent that contains catalyzer and alkaline solution and dissolve, at 70~130 ℃, carry out Suzuki coupling reaction 12~48 hours, stopped reaction cool to room temperature, separating-purifying reaction solution, the described blue emitting phosphor material of main part containing benzoglyoxaline unit that obtains following structural formula:
The preparation method of the described blue emitting phosphor material of main part containing benzoglyoxaline unit, wherein, oxygen-free environment is mainly that at least one gas in nitrogen, argon gas forms.
The preparation method of the described blue emitting phosphor material of main part containing benzoglyoxaline unit, wherein, described catalyzer is bi triphenyl phosphine dichloride palladium or tetra-triphenylphosphine palladium; Or,
Described catalyzer is the mixture of organic palladium and organophosphorus ligand, and in mixture, the molar weight of organophosphorus ligand is 4~8 times of organic palladium molar weight; Described organic palladium is palladium or three or two argon benzyl acetone two palladiums; Organophosphorus ligand is tri-o-tolyl phosphine or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl;
The mol ratio of described catalyzer and described compd A is 1:20~1:100.
The preparation method of the described blue emitting phosphor material of main part containing benzoglyoxaline unit, wherein, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium hydrogen carbonate solution; In described alkaline solution, the molar weight of alkali solute is 20 times of compd A molar weight.
The preparation method of the described blue emitting phosphor material of main part containing benzoglyoxaline unit, wherein, described organic solvent is at least one in toluene, DMF, tetrahydrofuran (THF).
The preparation method of the described blue emitting phosphor material of main part containing benzoglyoxaline unit, wherein, Suzuki coupling reaction temperature is 90~120 ℃, the reaction times is 24~36 hours.
The preparation method of the described blue emitting phosphor material of main part containing benzoglyoxaline unit, wherein, separating-purifying reaction solution comprises:
After coupling reaction stops, with dichloromethane extraction reaction solution repeatedly, preferably more than three times, merge organic phase, and with being spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain crude product, the sherwood oil that crude product is 10:1 by volume ratio again and ethyl acetate are leacheate, through silica gel column chromatography separation, obtain crystal thing, crystalline thing after 50 ℃ of dry 24h, is obtained to the described blue emitting phosphor material of main part containing benzoglyoxaline unit under vacuum.
An organic electroluminescence device, comprises substrate, stacks gradually anode layer, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and cathode layer on substrate one surface; Wherein, the material of each functional layer is as follows:
Substrate, its material is glass;
Anode layer, its material is tin indium oxide (ITO), is combined general designation ito glass, or ITO with substrate of glass;
Hole injection layer, its material is PEDOT:PSS;
Make hole transmission layer, its material is N, N '-bis-[(1-naphthyl)-N, N '-phenylbenzene]-1,1 '-xenyl-4,4 '-diamines (NPD);
Luminescent layer, its material is two (4,6-difluorophenyl pyridine-N, C2) pyridine formyl close ratio that iridium (III) is (FIrpic) 10% according to mass percent add to following structural formula containing formed doping mixing material in the blue emitting phosphor material of main part of benzoglyoxaline unit:
Electron transfer layer, its material are oxine aluminium (Alq
3)
Electron injecting layer, its material is LiF, and
Cathode layer, its material is Al.
Blue emitting phosphor material of main part containing benzoglyoxaline unit provided by the invention, has higher triplet, efficiency prevent that in luminescence process, energy returns to material of main part, greatly improve luminous efficiency; Meanwhile, the better heat stability that contains the blue emitting phosphor material of main part of benzoglyoxaline unit.
Separately, the preparation method of the above-mentioned blue emitting phosphor material of main part containing benzoglyoxaline unit, has adopted better simply synthetic route, thereby reduces technical process, and starting material are cheap and easy to get, and manufacturing cost is reduced.
Accompanying drawing explanation
Fig. 1 is the thermogravimetic analysis (TGA) figure containing the blue emitting phosphor material of main part of benzoglyoxaline unit that embodiment 1 makes.
Fig. 2 is the organic electroluminescence device structural representation that embodiment 5 makes.
Embodiment
In order to understand better the content of patent of the present invention, below by concrete example and legend, further illustrate technology case of the present invention, specifically comprise material preparation and device preparation, but these embodiments do not limit the present invention, compd A wherein, compd B is all bought and is obtained from the market.
Embodiment 1
The blue emitting phosphor material of main part containing benzoglyoxaline unit of the present embodiment, is 9-phenyl-3-(9-phenyl-2,7-bis-(3-(1-phenyl-1H-benzo [d] imidazoles-2-yl) phenyl)-9H-fluorenes-9-yl)-9H-carbazole, and preparation process is as follows:
Under argon shield, 3-(2, the bromo-9-phenyl-9H-of 7-bis-fluorenes-9-yl)-9-phenyl-9H-carbazole (128mg, 0.2mmol), 1-phenyl-2-(3-tetramethyl ethylene ketone boric acid ester phenyl)-1H-benzo [d] imidazoles (158mg, 0.4mmol) add in the flask that fills 10ml toluene solvant, after fully dissolving by salt of wormwood (2mL, 2mol/L) solution joins in flask, vacuumize deoxygenation and be filled with argon gas, then add bi triphenyl phosphine dichloride palladium (5.6mg, 0.008mmol); Flask is heated to 100 ℃ and carries out Suzuki coupling reaction 24h.Stopped reaction cool to room temperature, with dichloromethane extraction reaction solution repeatedly, merge organic phase, and with being spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain crude product, the sherwood oil that crude product is 10:1 by volume ratio again and ethyl acetate are leacheate, through silica gel column chromatography separation, obtain crystal thing, crystalline thing after 50 ℃ of dry 24h, is obtained to the described blue emitting phosphor material of main part containing benzoglyoxaline unit under vacuum.Productive rate is 80%.
Mass spectrum: m/z1019.4(M
++ 1); Ultimate analysis (%) C
75h
49n
5: theoretical value: C88.29, H4.84, N6.86; Measured value: C88.36, H4.75, N6.90.
Fig. 1 is the thermogravimetic analysis (TGA) figure containing the blue emitting phosphor material of main part of benzoglyoxaline unit that embodiment 1 makes; Thermogravimetic analysis (TGA) is completed by the measurement of Perkin-Elmer Series7 Thermo System, and all measurements all complete in atmosphere at room temperature, 5% thermal weight loss temperature (T
d) be 455 ℃.
Embodiment 2
The present embodiment containing the blue emitting phosphor material of main part of benzoglyoxaline unit, i.e. 9-phenyl-3-(9-phenyl-2,7-bis-(3-(1-phenyl-1H-benzo [d] imidazoles-2-yl) phenyl)-9H-fluorenes-9-yl)-9H-carbazole, preparation process is as follows:
Under nitrogen and the protection of argon gas gas mixture; by 3-(2; the bromo-9-phenyl-9H-of 7-bis-fluorenes-9-yl)-9-phenyl-9H-carbazole (192mg; 0.3mmol), 1-phenyl-2-(3-tetramethyl ethylene ketone boric acid ester phenyl)-1H-benzo [d] imidazoles (261mg; 0.66mmol) add in the two-mouth bottle of 50mL specification with 15mL tetrahydrofuran (THF); after fully dissolving, pass into after the about 20min of gas mixture air-discharging of nitrogen and argon gas; then by tetra-triphenylphosphine palladium (4mg; 0.003mmol) add wherein; after fully dissolving, add again sodium bicarbonate (3mL, 2mol/L) solution.After the about 10min of gas mixture air-discharging of fully logical nitrogen and argon gas, two-mouth bottle is joined to 70 ℃ and carry out Suzuki coupling reaction 48h again.Stopped reaction cool to room temperature, with dichloromethane extraction reaction solution repeatedly, merge organic phase, and with being spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain crude product, the sherwood oil that crude product is 10:1 by volume ratio again and ethyl acetate are leacheate, through silica gel column chromatography separation, obtain crystal thing, crystalline thing after 50 ℃ of dry 24h, is obtained to the described blue emitting phosphor material of main part containing benzoglyoxaline unit under vacuum.Productive rate is 84%.
Embodiment 3
The present embodiment containing the blue emitting phosphor material of main part of benzoglyoxaline unit, i.e. 9-phenyl-3-(9-phenyl-2,7-bis-(3-(1-phenyl-1H-benzo [d] imidazoles-2-yl) phenyl)-9H-fluorenes-9-yl)-9H-carbazole, preparation process is as follows:
Under nitrogen protection, by 3-(2, the bromo-9-phenyl-9H-of 7-bis-fluorenes-9-yl)-9-phenyl-9H-carbazole (192mg, 0.3mmol), 1-phenyl-2-(3-tetramethyl ethylene ketone boric acid ester phenyl)-1H-benzo [d] imidazoles (285mg, 0.72mmol), palladium (3.5mg, 0.015mmol) He three (o-methoxyphenyl) phosphine (21mg, 0.06mmol) join the N that fills 12mL, in the flask of dinethylformamide, after fully dissolving, add salt of wormwood (3mL, 2mol/L) solution leads to after the about 30min of nitrogen purge gas subsequently in flask; Flask is heated to 130 ℃ and carries out Suzuki coupling reaction 12h.Stopped reaction cool to room temperature, with dichloromethane extraction reaction solution repeatedly, merge organic phase, and with being spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain crude product, the sherwood oil that crude product is 10:1 by volume ratio again and ethyl acetate are leacheate, through silica gel column chromatography separation, obtain crystal thing, crystalline thing after 50 ℃ of dry 24h, is obtained to the described blue emitting phosphor material of main part containing benzoglyoxaline unit under vacuum.Productive rate is 82%.
Embodiment 4
The present embodiment containing the blue emitting phosphor material of main part of benzoglyoxaline unit, i.e. 9-phenyl-3-(9-phenyl-2,7-bis-(3-(1-phenyl-1H-benzo [d] imidazoles-2-yl) phenyl)-9H-fluorenes-9-yl)-9H-carbazole, preparation process is as follows:
Under nitrogen protection; by 3-(2; the bromo-9-phenyl-9H-of 7-bis-fluorenes-9-yl)-9-phenyl-9H-carbazole (192mg; 0.3mmol), 1-phenyl-2-(3-tetramethyl ethylene ketone boric acid ester phenyl)-1H-benzo [d] imidazoles (285mg; 0.72mmol), three dibenzalacetone two palladium (9mg; 0.009mmol) with 2-dicyclohexyl phosphine-2 '; 6 '-dimethoxy-biphenyl (29mg; 0.072mmol) join the N that fills 12mL; in the flask of dinethylformamide; after fully dissolving, add sodium carbonate (3mL, 2mol/L) solution.In flask, lead to after the about 30min of nitrogen purge gas subsequently; Flask is heated to 120 ℃ and carries out Suzuki coupling reaction 36h.Stopped reaction cool to room temperature, with dichloromethane extraction reaction solution repeatedly, merge organic phase, and with being spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain crude product, the sherwood oil that crude product is 10:1 by volume ratio again and ethyl acetate are leacheate, through silica gel column chromatography separation, obtain crystal thing, crystalline thing after 50 ℃ of dry 24h, is obtained to the described blue emitting phosphor material of main part containing benzoglyoxaline unit under vacuum.Productive rate is 79%.
Embodiment 5
The present embodiment is organic electroluminescence device, it adopts the arbitrary 9-phenyl-3-making of above-described embodiment 1 to 4 (9-phenyl-2,7-bis-(3-(1-phenyl-1H-benzo [d] imidazoles-2-yl) phenyl)-9H-fluorenes-9-yl)-9H-carbazole as the material of main part of luminescent layer.
This organic electroluminescence device, as shown in Figure 2, comprises and stacks gradually structure: substrate 1/ anode layer 2/ hole injection layer 3/ hole transmission layer 4/ luminescent layer 5/ electron transfer layer 6/ electron injecting layer 7/ cathode layer 8; Wherein, slash "/" represents laminate structure.
Functional layer material and the thickness of above-mentioned organic electroluminescence device are as follows:
Substrate 1 adopts glass;
Anode layer 2 adopts ITO(tin indium oxide compound), thickness 150nm; ITO preparation, after glass surface, is called for short ito glass;
The material of hole injection layer 3 is PEDOE:PSS, and thickness is 30nm; Wherein, PEDOT is poly-3,4-ethylenedioxy thiazole, and PSS is polystyrene-sulfonic acid matrix material, and PEDOT:PSS is expressed as mixing of PEDOT and PSS;
The material of hole transmission layer 4 is N, N '-bis-[(1-naphthyl)-N, N '-phenylbenzene]-1, and 1 '-xenyl-4,4 '-diamines (NPD), thickness is 20nm;
The material of luminescent layer 5 is two (4,6-difluorophenyl pyridine-N, C2) pyridine formyl closes iridium (III) (FIrpic) as object luminescent material, mass ratio according to 10% is doped to 9-phenyl-3-(9-phenyl-2,7-bis-(3-(1-phenyl-1H-benzo [d] imidazoles-2-yl) phenyl)-9H-fluorenes-9-yl) the doping mixing material obtaining in-9H-carbazole (representing with P) material of main part, be expressed as P:FIrpic, thickness is 20nm;
The material of electron transfer layer 6 is oxine aluminium (Alq
3), thickness is 30nm;
The material of electron injecting layer 7 is lithium fluoride (LiF), and thickness is 1.5nm;
The material of cathode layer 8 is aluminium (Al), and thickness is 150nm.
Above-mentioned organic electroluminescence device can be expressed as:
Glass/ITO/PEDOT:PSS/NPD/P:FIrpic/Alq
3/ LiF/Al; Wherein, slash "/" represents laminate structure.
This organic electroluminescence device, its preparation technology is as follows:
First, at the glass surface cleaning up, by magnetron sputtering, prepare one deck ITO layer, obtain ito glass;
Secondly, ito glass is moved in vacuum evaporation equipment, at ITO layer surface spin coating PEDOT:PSS;
Finally, on PEDOT:PSS surface, stack gradually evaporation NPD, P:FIrpic, Alq
3, LiF, Al;
After above-mentioned processing step completes, obtain organic electroluminescence device.
Electric current-the brightness-voltage characteristic of organic electroluminescence device is to be completed by the Keithley source measuring system (Keithley2400Sourcemeter, Keithley2000Cuirrentmeter) with correction silicon photoelectric diode.
Test result is, the maximum current efficiency of organic electroluminescence device is 6.9cd/A, and high-high brightness is 17630cd/m
2.Result shows that polymer body material property of the present invention is better, is a kind of very promising Blue-light emitting host material.
Claims (10)
1. containing a blue emitting phosphor material of main part for benzoglyoxaline unit, it is characterized in that, its structural formula is as follows:
2. contain a preparation method for the blue emitting phosphor material of main part of benzoglyoxaline unit, it is characterized in that, comprise the steps:
The compd A and the B that provide respectively following structural formula to represent,
Under oxygen-free environment, the compd A that is 1:2~2.4 by mol ratio and B are added in the organic solvent that contains catalyzer and alkaline solution and dissolve, at 70~130 ℃, carry out Suzuki coupling reaction 12~48 hours, stopped reaction cool to room temperature, separating-purifying reaction solution, the described blue emitting phosphor material of main part containing benzoglyoxaline unit that obtains following structural formula:
3. the preparation method of the blue emitting phosphor material of main part containing benzoglyoxaline unit according to claim 2, is characterized in that, described catalyzer is bi triphenyl phosphine dichloride palladium or tetra-triphenylphosphine palladium; The mol ratio of described catalyzer and described compd A is 1:20~1:100.
4. the preparation method of the blue emitting phosphor material of main part containing benzoglyoxaline unit according to claim 2, it is characterized in that, described catalyzer is the mixture of organic palladium and organophosphorus ligand, and in mixture, the molar weight of organophosphorus ligand is 4~8 times of organic palladium molar weight; The mol ratio of described catalyzer and described compd A is 1:20~1:100.
5. the preparation method of the blue emitting phosphor material of main part containing benzoglyoxaline unit according to claim 4, is characterized in that, described organic palladium is palladium or three or two argon benzyl acetone two palladiums; Organophosphorus ligand is tri-o-tolyl phosphine or 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl.
6. the preparation method of the blue emitting phosphor material of main part containing benzoglyoxaline unit according to claim 2, is characterized in that, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium hydrogen carbonate solution; In described alkaline solution, the molar weight of alkali solute is 20 times of compd A molar weight.
7. the preparation method of the blue emitting phosphor material of main part containing benzoglyoxaline unit according to claim 2, is characterized in that, described organic solvent is at least one in toluene, DMF, tetrahydrofuran (THF).
8. the preparation method of the blue emitting phosphor material of main part containing benzoglyoxaline unit according to claim 2, is characterized in that, Suzuki coupling reaction temperature is 90~120 ℃, and the reaction times is 24~36 hours.
9. the preparation method of the blue emitting phosphor material of main part containing benzoglyoxaline unit according to claim 2, is characterized in that, separating-purifying reaction solution comprises:
After coupling reaction stops, with dichloromethane extraction reaction solution repeatedly, merge organic phase, and with being spin-dried for after anhydrous magnesium sulfate drying organic phase, obtain crude product, the sherwood oil that crude product is 10:1 by volume ratio again and ethyl acetate are leacheate, through silica gel column chromatography separation, obtain crystal thing, crystalline thing after 50 ℃ of dry 24h, is obtained to the described blue emitting phosphor material of main part containing benzoglyoxaline unit under vacuum.
10. an organic electroluminescence device, is characterized in that, the luminescent layer material of this organic electroluminescence device is that two (4,6-difluorophenyl pyridine-N, C2) pyridine formyls close ratio that iridium is 10% according to mass percent and add structural formula to and be
containing formed doping mixing material in the blue emitting phosphor material of main part of benzoglyoxaline unit.
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US11299466B2 (en) | 2016-04-12 | 2022-04-12 | Lg Chem, Ltd. | Compound, and organic electronic element comprising same |
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Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US11299466B2 (en) | 2016-04-12 | 2022-04-12 | Lg Chem, Ltd. | Compound, and organic electronic element comprising same |
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CN106905242B (en) * | 2017-03-02 | 2019-07-12 | 中国矿业大学 | The two poles of the earth configuration pyrenyl containing benzimidazole unit blue light material and preparation method and application |
CN107011268A (en) * | 2017-05-27 | 2017-08-04 | 中国矿业大学 | The 1,3,6,8 4 substitution pyrenyl materials and preparation method and application of bipolarity D π A configurations |
CN107011268B (en) * | 2017-05-27 | 2019-07-23 | 中国矿业大学 | The 1,3,6,8- tetra- of bipolarity D- π-A configuration replaces pyrenyl material and preparation method and application |
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Application publication date: 20141203 |