CN103896931A - Organic semiconductor material and preparation method thereof, and electroluminescent device - Google Patents

Organic semiconductor material and preparation method thereof, and electroluminescent device Download PDF

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CN103896931A
CN103896931A CN201210578673.6A CN201210578673A CN103896931A CN 103896931 A CN103896931 A CN 103896931A CN 201210578673 A CN201210578673 A CN 201210578673A CN 103896931 A CN103896931 A CN 103896931A
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semiconductor material
organic semiconductor
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周明杰
王平
张振华
张娟娟
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Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Engineering Co Ltd
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Oceans King Lighting Science and Technology Co Ltd
Shenzhen Oceans King Lighting Engineering Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
    • 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
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom

Abstract

The invention relates to an organic semiconductor material which has a chemical formula as described in the specification. The organic semiconductor material has bipolar carrier transport capability, which enables hole and electron transport in a luminescent layer to be balanced; meanwhile, the organic semiconductor material has a high triplet energy level and excellent thermal stability, thereby effectively preventing energy from returning back to a host material in the process of luminescence and substantially improving luminescent efficiency. The invention further provides a preparation method for the organic semiconductor material and an electroluminescent device containing the organic semiconductor material.

Description

A kind of organic semiconductor material, preparation method and electroluminescent device
Technical field
The invention belongs to field of photovoltaic materials, be specifically related to a kind of organic semiconductor material, preparation method and electroluminescent device.
Background technology
Organic electroluminescence device has that driving voltage is low, fast response time, angular field of view are 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.But, 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 blue phosphorescent device is little efficiently, 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
For addressing the above problem, the invention provides a kind of organic semiconductor material, this organic semiconductor material has bipolarity carrier transport ability, makes hole and electric transmission balance in luminescent layer; Also there is higher triplet and good thermal stability simultaneously, effectively prevent that in luminescence process, energy returns to material of main part, greatly improved luminous efficiency, organic semiconductor material of the present invention provides new selectable kind for bipolarity ruddiness phosphorescent light body material.The present invention also provides the preparation method of this organic semiconductor material, and the electroluminescent device that comprises this organic semiconductor material.
On the one hand, the invention provides a kind of organic semiconductor material, the chemical formula of described organic semiconductor material is as follows:
Second aspect, the invention provides a kind of preparation method of organic semiconductor material, comprises the steps:
Compd A is provided:
Figure BDA00002663202900022
and compd B: under inert atmosphere, be that 1:2～2.4 are added in the organic solvent that contains catalyzer and alkaline solution and at 70～130 DEG C, carry out Suzuki coupling reaction 12～48 hours by compd A and compd B according to mol ratio, it is as follows that stopped reaction obtains the chemical formula of organic semiconductor material:
Figure BDA00002663202900024
Preferably, the preparation method of described organic semiconductor material further comprises post-processing step, described post-processing step is specially: stopped reaction is obtained to organic semiconductor material methylene dichloride and extract, after merging organic phase, adopt anhydrous magnesium sulfate drying, and the mixed solvent that adopts sherwood oil and ethyl acetate as leacheate through layer of silica gel separating-purifying, vacuum-drying obtain target product.
Preferably, described organic solvent is selected from least one in toluene, DMF, tetrahydrofuran (THF).
Preferably, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium hydrogen carbonate solution, and the solute in described alkaline solution and the mol ratio of compd A are 20:1 ~ 50:1.
Preferably, described organic palladium is bi triphenyl phosphine dichloride palladium, tetra-triphenylphosphine palladium, palladium and tri-o-tolyl phosphine mixture or three or two argon benzyl acetone two palladiums and 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl mixture.Wherein, the molar weight of phosphine part is 4～8 times of organic palladium molar weight.
Preferably, the mol ratio of described organic palladium and described compd A is 1:20 ~ 1:100.
The third aspect, the invention provides a kind of electroluminescent device, comprise the substrate with anode, luminescent layer and the cathode layer that stack gradually, described luminescent layer is the mixture of material of main part and guest materials, wherein material of main part organic semiconductor material as follows:
Figure BDA00002663202900031
guest materials is three [1-phenyl isoquinolin quinoline-C2, N] iridium, two (4,6-difluorophenyl pyridine-N, C2) pyridine formyl close iridium, [two (2 ', 4 '-difluorophenyl) pyridine] [four (1-pyrazolyl) boron] closes iridium or [two (2 ', 4 '-difluorophenyl) pyridine] (tetrazolium pyridine) closes iridium.
Preferably, the mass percent of described material of main part and described guest materials is 5%～15%.
Preferably, anode material is indium zinc oxide or zinc oxide aluminum, and negative electrode is metallic aluminium, silver, gold or nickel.
The invention provides a kind of organic semiconductor material, preparation method and electroluminescent device, there is following beneficial effect: there is bipolarity carrier transport ability, make hole and electric transmission balance in luminescent layer; Also have higher triplet and good thermal stability simultaneously, effectively prevent that in luminescence process, energy returns to material of main part, greatly improved luminous efficiency, synthetic method is simple, can be used for ruddiness phosphorescent light body material.
Brief description of the drawings
The structural representation of Fig. 1 organic electroluminescence device that to be organic semiconductor material to make in embodiment 1 make as material of main part;
Fig. 2 is the thermogravimetic analysis (TGA) figure of the organic semiconductor material that makes in embodiment 1.
Embodiment
In order to understand better the content of patent of the present invention, further illustrate technology case of the present invention below by concrete example and legend, specifically comprise material preparation and device preparation, but these embodiments do not limit the present invention, wherein monomer A, monomers B are all bought and are obtained from the market.
The invention provides a kind of organic semiconductor material, the chemical formula of described organic semiconductor material is as follows:
Figure BDA00002663202900041
This organic semiconductor material has bipolarity carrier transport ability, makes hole and electric transmission balance in luminescent layer; Also have higher triplet and good thermal stability simultaneously, effectively prevent that in luminescence process, energy returns to material of main part, greatly improved luminous efficiency, therefore organic semiconductor material of the present invention has bipolarity ruddiness phosphorescent light body material.
The preparation method who the invention provides a kind of organic semiconductor material, comprises the steps:
Compd A is provided:
Figure BDA00002663202900042
and compd B:
Figure BDA00002663202900043
under inert atmosphere, be that 1:2～2.4 are added in the organic solvent that contains catalyzer and alkaline solution and at 70～130 DEG C, carry out Suzuki coupling reaction 12～48 hours by compd A and compd B according to mol ratio, it is as follows that stopped reaction obtains the chemical formula of organic semiconductor material:
Figure BDA00002663202900044
In specific embodiment, the preparation method of described organic semiconductor material further comprises post-processing step, described post-processing step is specially: stopped reaction is obtained to organic semiconductor material methylene dichloride and extract, after merging organic phase, adopt anhydrous magnesium sulfate drying, and the mixed solvent that adopts sherwood oil and ethyl acetate as leacheate through layer of silica gel separating-purifying, vacuum-drying obtain target product.
In specific embodiment, the volume ratio of sherwood oil and ethyl acetate is 10:1～8:1;
In specific embodiment, vacuum drying condition is to be dried 12～24 hours at 50～70 DEG C;
In specific embodiment, described organic solvent is selected from least one in toluene, DMF, tetrahydrofuran (THF).
In specific embodiment, described alkaline solution is selected from least one in sodium carbonate solution, solution of potassium carbonate and sodium hydrogen carbonate solution, and the solute in described alkaline solution and the mol ratio of compd A are 20:1 ~ 50:1.
In specific embodiment, described organic palladium is bi triphenyl phosphine dichloride palladium, tetra-triphenylphosphine palladium, palladium and tri-o-tolyl phosphine mixture or three or two argon benzyl acetone two palladiums and 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl mixture.Wherein, the molar weight of phosphine part is 4～8 times of organic palladium molar weight.
In specific embodiment, described organic palladium and the mol ratio of described compd A are 1:20 ~ 1: 100.
Adopted better simply synthetic route, thereby reduced technical process, starting material are cheap and easy to get, and manufacturing cost is reduced.
The invention provides a kind of electroluminescent device, comprise the substrate with anode, luminescent layer and the cathode layer that stack gradually, described luminescent layer is the mixture of material of main part and guest materials, wherein material of main part organic semiconductor material as follows: guest materials is three [1-phenyl isoquinolin quinoline-C2, N] iridium, two (4,6-difluorophenyl pyridine-N, C2) pyridine formyl close iridium, [two (2 ', 4 '-difluorophenyl) pyridine] [four (1-pyrazolyl) boron] closes iridium or [two (2 ', 4 '-difluorophenyl) pyridine] (tetrazolium pyridine) closes iridium.
In specific embodiment, the mass percent of described guest materials and described material of main part is 5%～15%.
In specific embodiment, anode material is indium zinc oxide or zinc oxide aluminum, and negative electrode is metallic aluminium, silver, gold or nickel.
Organic luminescent device transmitting blue light based on this material, and luminous efficiency is high.
Embodiment 1:
2,5-bis-(4-(9H-carbazole-9-yl) phenyl) the preparation process preparation process of thiophene sulfone is as follows:
Under argon shield, by 2,5-dibromo thiophene sulfone (55mg, 0.2mmol), 9-(4-tetramethyl ethylene ketone boric acid ester phenyl)-9H-carbazole (148mg, 0.4mmol) adds 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 DEG C and carries out Suzuki coupling reaction 24h.Stopped reaction cool to room temperature, with dichloromethane extraction three times, merge organic phase, after anhydrous magnesium sulfate drying, be spin-dried for, obtain this 2,5-bis-(4-(9H-carbazole-9-yl) phenyl) thiophene sulfone organic semiconductor material, then adopt sherwood oil: ethyl acetate volume ratio is that 10:1 is that leacheate separates and obtains white crystal through silica gel column chromatography.The last lower 50 DEG C of dry 24h of vacuum.Productive rate is 80%.
Test data of experiment: mass spectrum: m/z598.2(M ++ 1);
Ultimate analysis (%) C 40h 26n 2o 2s: theoretical value C80.24, H4.38, N4.68, O5.34S5.36; Measured value: C80.22, H4.47, N4.65, O5.30, S5.39.
Are thermogravimetic analysis (TGA) figure of the organic semiconductor material prepared of the present embodiment referring to accompanying drawing 2, thermogravimetric curve (TGA) test is carried out on TA SDT2960instruments, and under nitrogen gas stream protection, heat-up rate is 10K/min.5% thermal weight loss temperature is 375 DEG C as seen from the figure.
By test for low temperature phosphorescence spectrum, instrument is FS modular fluorometer/pectrophosphorimeter, to investigate its triplet state emission characteristic.Under the liquid nitrogen of 77K, bill of material reveals very strong phosphorescent emissions, and emission peak is at 492nm, and corresponding triplet energy state is 2.52eV, is much higher than phosphor material three [1-phenyl isoquinolin quinoline-C2, N] iridium (III) [Ir (piq) 3] triplet energy state (1.90eV), test data result shows that our material can be used as ruddiness phosphorescent light body material.
Embodiment 2:
2,5-bis-(4-(9H-carbazole-9-yl) phenyl) the preparation process preparation process of thiophene sulfone is as follows:
Figure BDA00002663202900071
Under nitrogen and the protection of argon gas gas mixture; by 2; 5-dibromo thiophene sulfone (82mg; 0.3mmol), 9-(4-tetramethyl ethylene ketone boric acid ester phenyl)-9H-carbazole (244mg; 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 heated to 70 DEG C and carries out Suzuki coupling reaction 48h again.Stopped reaction cool to room temperature, with dichloromethane extraction three times, merge organic phase, after anhydrous magnesium sulfate drying, be spin-dried for, obtain this 2,5-bis-(4-(9H-carbazole-9-yl) phenyl) thiophene sulfone organic semiconductor material, then adopt sherwood oil: ethyl acetate volume ratio is that 10:1 is that leacheate separates and obtains white crystal through silica gel column chromatography.The last lower 50 DEG C of dry 24h of vacuum.Productive rate is 85%.
Embodiment 3:
2,5-bis-(4-(9H-carbazole-9-yl) phenyl) the preparation process preparation process of thiophene sulfone is as follows:
Figure BDA00002663202900072
Under nitrogen protection, by 2,5-dibromo thiophene sulfone (82mg, 0.3mmol), 9-(4-tetramethyl ethylene ketone boric acid ester phenyl)-9H-carbazole (266mg, 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 DEG C and carries out Suzuki coupling reaction 12h.Stopped reaction cool to room temperature, with dichloromethane extraction three times, merge organic phase, after anhydrous magnesium sulfate drying, be spin-dried for, obtain this 2,5-bis-(4-(9H-carbazole-9-yl) phenyl) thiophene sulfone organic semiconductor material, then adopt sherwood oil: ethyl acetate volume ratio is that 10:1 is that leacheate separates and obtains white crystal through silica gel column chromatography.The last lower 50 DEG C of dry 24h of vacuum.Productive rate is 82%.
Embodiment 4:
2,5-bis-(4-(9H-carbazole-9-yl) phenyl) the preparation process preparation process of thiophene sulfone is as follows:
Under nitrogen protection; by 2; 5-dibromo thiophene sulfone (82mg; 0.3mmol), 9-(4-tetramethyl ethylene ketone boric acid ester phenyl)-9H-carbazole (266mg; 0.72mmol), three or two argon benzyl acetone 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 DEG C and carries out Suzuki coupling reaction 36h.Stopped reaction cool to room temperature, with dichloromethane extraction three times, merge organic phase, after anhydrous magnesium sulfate drying, be spin-dried for, obtain this 2,5-bis-(4-(9H-carbazole-9-yl) phenyl) thiophene sulfone organic semiconductor material, then adopt sherwood oil: ethyl acetate (10:1) is that leacheate separates and obtains white crystal through silica gel column chromatography.The last lower 50 DEG C of dry 24h of vacuum.Productive rate is 86%.
Application Example
Organic electroluminescence device 300, as Fig. 1, it comprises substrate 301 to its structure, anode 302, hole injection layer 303, hole transmission layer 304, luminescent layer 305, electron transfer layer 306, electronic injection buffer layer 307, negative electrode 308.
In the present embodiment, the material of substrate 301 is glass, vacuum plating anode 302 successively in substrate 301, hole injection layer 303, hole transmission layer 304, luminescent layer 305, electron transfer layer 306, electronic injection buffer layer 307, negative electrode 308, it is the tin indium oxide of 10 ~ 20 Ω/ that anode 302 adopts square resistance, thickness is 150nm, hole injection layer 303 adopts poly-(3, 4-ethene dioxythiophene)-polystyrolsulfon acid, thickness is 30nm, hole transmission layer 304 adopts N, N '-phenylbenzene-N, N '-(1-naphthyl)-1, 1 '-biphenyl-4, 4 '-diamines, thickness is 20nm, the compound 2 that luminescent layer 305 main body luminescent materials adopt the invention process 1 to prepare, 5-bis-(4-(9H-carbazole-9-yl) phenyl) thiophene sulfone, and taking material of main part as benchmark object luminescent material three [the 1-phenyl isoquinolin quinoline-C2 of doping mass percent as 10%, N] iridium (III), luminescent layer 305 thickness are 20nm, electron transfer layer 306 adopts 5 (4, 7-phenylbenzene-1, 10-phenanthroline, thickness is 30nm, electronic injection buffer layer 307 adopts lithium fluoride, thickness is 1nm, negative electrode 308 adopts metallic aluminium, thickness is 100nm.
Organic layer and metal level all adopt thermal evaporation process deposits to complete, and vacuum tightness is 10 -3～10 -5pa, the thickness of film adopts film thickness monitoring instrument to monitor, and except guest materials, the vaporator rate of all organic materialss is second, the vaporator rate of lithium fluoride is
Figure BDA00002663202900092
second, the vaporator rate of metallic aluminium is
Figure BDA00002663202900093
second.
This electroluminescent device has higher luminous efficiency, can be widely used in the luminous field such as blueness or white.Electric current-the brightness-voltage characteristic of device is that all measurements that completed by the Keithley source measuring system with correction silicon photoelectric diode (Keithley 2400 Sourcemeter, Keithley 2000 Cuirrentmeter) all complete in atmosphere at room temperature.Result shows: the trigger voltage of device is 3.4V, at 1000cd/m 2brightness under, luminous efficiency is 12.6lm/W.
The above embodiment has only expressed several embodiment of the present invention, and it describes comparatively concrete and detailed, but can not therefore be interpreted as the restriction to the scope of the claims of the present invention.It should be pointed out that for the person of ordinary skill of the art, without departing from the inventive concept of the premise, can also make some distortion and improvement, these all belong to protection scope of the present invention.Therefore, the protection domain of patent of the present invention should be as the criterion with claims.

Claims (10)

1. an organic semiconductor material, is characterized in that, the chemical formula of described organic semiconductor material is as follows:
Figure FDA00002663202800011
2. a preparation method for organic semiconductor material, is characterized in that, comprises the steps:
Compd A is provided: and compd B:
Figure FDA00002663202800013
under inert atmosphere, be that 1:2～2.4 are added in the organic solvent that contains catalyzer and alkaline solution and at 70～130 DEG C, carry out Suzuki coupling reaction 12～48 hours by compd A and compd B according to mol ratio, it is as follows that stopped reaction obtains the chemical formula of organic semiconductor material:
Figure FDA00002663202800014
3. preparation method as claimed in claim 2, it is characterized in that, the preparation method of described organic semiconductor material further comprises post-processing step, described post-processing step is specially: stopped reaction is obtained to organic semiconductor material methylene dichloride and extract, after merging organic phase, adopt anhydrous magnesium sulfate drying, and the mixed solvent that adopts sherwood oil and ethyl acetate as leacheate through layer of silica gel separating-purifying, vacuum-drying obtain target product.
4. preparation method as claimed in claim 2, is characterized in that, described organic solvent is selected from least one in toluene, DMF, tetrahydrofuran (THF).
5. preparation method as claimed in 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, and the solute in described alkaline solution and the mol ratio of compd A are 20:1 ~ 50:1.
6. preparation method as claimed in claim 2, it is characterized in that, described organic palladium is bi triphenyl phosphine dichloride palladium, tetra-triphenylphosphine palladium, palladium and tri-o-tolyl phosphine mixture or three or two argon benzyl acetone two palladiums and 2-dicyclohexyl phosphine-2 ', 6 '-dimethoxy-biphenyl mixture, wherein, the molar weight of phosphine part is 4～8 times of organic palladium molar weight.
7. preparation method as claimed in claim 2, is characterized in that, the mol ratio of described organic palladium and described compd A is 1:20 ~ 1:100.
8. an electroluminescent device, is characterized in that, comprises the substrate with anode, luminescent layer and the cathode layer that stack gradually, and described luminescent layer is the mixture of material of main part and guest materials, wherein material of main part organic semiconductor material as follows:
guest materials is three [1-phenyl isoquinolin quinoline-C2, N] iridium, two (4,6-difluorophenyl pyridine-N, C2) pyridine formyl close iridium, [two (2 ', 4 '-difluorophenyl) pyridine] [four (1-pyrazolyl) boron] closes iridium or [two (2 ', 4 '-difluorophenyl) pyridine] (tetrazolium pyridine) closes iridium.
9. electroluminescent device as claimed in claim 8, is characterized in that, the mass percent of described material of main part and described guest materials is 5%～15%.
10. electroluminescent device as claimed in claim 8, is characterized in that, described anode material is indium zinc oxide or zinc oxide aluminum, and negative electrode is metallic aluminium, silver, gold or nickel.
CN201210578673.6A 2012-12-27 2012-12-27 Organic semiconductor material and preparation method thereof, and electroluminescent device Pending CN103896931A (en)

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CN106318376A (en) * 2015-06-24 2017-01-11 上海和辉光电有限公司 Light-emitting compound

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WO2010090123A1 (en) * 2009-02-04 2010-08-12 コニカミノルタホールディングス株式会社 Organic photoelectric conversion element, solar cell using same, and optical sensor array

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Application publication date: 20140702