CN102898854B - Organic dye taking alkoxy substituted fluorene unit-containing triarylated amine as donor and application thereof in dye-sensitized solar cell - Google Patents
Organic dye taking alkoxy substituted fluorene unit-containing triarylated amine as donor and application thereof in dye-sensitized solar cell Download PDFInfo
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02E10/542—Dye sensitized solar cells
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Abstract
The invention provides an organic dye taking alkoxy substituted fluorene unit-containing triarylated amine as a donor and the application of the organic dye in a dye-sensitized solar cell, belonging to the field of the organic dye. The organic dye takes alkoxy substituted fluorene as the unit of a triarylated amine donor, so that the electron pushing capability of the dye donor part can be improved due to the alkoxy substituted fluorene-containing structure unit, the gathering of small molecules can be reduced due to the use of the fluorene unit, the electron recombination in the cell can be reduced, the open-circuit voltage of the cell can be effectively improved, and the gathering of the molecule can be reduced and the dissolubility of the dye can be improved due to the introduction of alkyl chain, so that a device can be conveniently optimized. The organic dye provided by the invention is simple in synthetic route, and easy to purify; and according to the dye-sensitized solar cell prepared by the organic dye provided by the invention, the open-circuit voltage reaches to 948 millivolts, the short-circuit photocurrent reaches to 14.36 milliamperes in every square centimeter, and the power conversion efficiency reaches 9.9%.
Description
Technical field
The present invention relates to the organic dye technical field, be specifically related to a kind ofly take three arylamine that contain alkoxyl group substituted fluorene unit and be the organic dye to body and the application in dye-sensitized solar cells.
Background technology
Sun power is as a kind of clean energy, under traditional energy faces a crisis situation at present, and will be by development and utilization more widely.In current area of solar cell, silica-based solar cell is occupied an leading position, but its manufacturing cost is higher, and the method that there is no substitutes traditional energy on a large scale.Dye sensitization solar battery, be subject to paying close attention to widely both at home and abroad and studying as a kind of type of exciton based on organic photoelectric functional material solar cell of cheapness.1991, the reported for work breakthrough work (Nature 1991,353,737) of dye sensitized nano crystal salar battery of senior engineer Gr professor tzel of Swiss Confederation, opened the upsurge of nanostructure organic photovoltaic battery research.But in high-efficiency battery, the use of noble ruthenium complex dye is denounced by the public for a long time, therefore, the exploitation that does not contain the dyestuff of precious metal is one of research emphasis of dye sensitization solar battery always.2011, through the long effort of a large amount of researchists, with zinc protoporphyrin dyestuff YD2-o-C8 and pure organic dye Y123, be total to the battery of sensitization, obtained the progress (Science of effciency of energy transfer 12.3 %, 2011,334,629), not only break away from the dependence to precious metal, and on energy conversion efficiency, obtained breakthrough.This class battery, not only realized widening of absorption spectrum, and the solid space design that intercepts slowed down electronics in the semiconductor film and the compound speed of redox electrolytes matter effectively, realized the high output voltage of device.Similar to zinc protoporphyrin class dyestuff, pure organic dye has more cheap preparation cost and higher molar absorption coefficient equally, and the optional structural unit of pure organic dye is abundanter.
Summary of the invention
The objective of the invention is in order to solve existing organic dye owing to containing the problem that makes high expensive with precious metal, take three arylamine that contain alkoxyl group substituted fluorene unit and be the organic dye to body and the application in dye-sensitized solar cells and provide a kind of.
The invention provides and a kind ofly take three arylamine that contain alkoxyl group substituted fluorene unit and be the organic dye to body, structure is suc as formula shown in (V):
In formula (V), R
1For C
1~ C
18Alkyl; R
2, R
3, R
4And R
5Independent separately is C
1~ C
18Alkyl; Y is H, Na or K ion;
Ar
1For
Or
, R wherein
6And R
7Independent separately is hydrogen atom, C
1~ C
18Alkyl or C
1~ C
18Alkoxyl group, R
8And R
9Independent separately is hydrogen atom or C
1~ C
18Alkyl;
Ar
2For
Or
, R wherein
10, R
13And R
14Independent separately is hydrogen atom, C
1~ C
18Alkyl or C
1~ C
18Alkoxyl group, R
11And R
12Independent separately is C
1~ C
18Alkyl.
Preferably, describedly take three arylamine that contain alkoxyl group substituted fluorene unit and have the structure shown in formula I as the organic dye to body:
Preferably, describedly take three arylamine that contain alkoxyl group substituted fluorene unit and have the structure shown in formula II as the organic dye to body:
Preferably, describedly take three arylamine that contain alkoxyl group substituted fluorene unit and have the structure shown in formula III as the organic dye to body:
The invention provides that a kind of technique scheme is described take three arylamine that contain alkoxyl group substituted fluorene unit and be the application of the organic dye to body in dye-sensitized solar cells.
The present invention also provides a kind of organic dye sensitized solar cell, and to be that technique scheme is described take three arylamine that contain alkoxyl group substituted fluorene unit and be the organic dye to body dye coating.
Beneficial effect
The invention provides and a kind ofly take three arylamine that contain alkoxyl group substituted fluorene unit and be the organic dye to body and the application in dye-sensitized solar cells.This organic dye has formula (V) structure, the present invention is usingd fluorenes that alkoxyl group replaces as the unit of three arylamine to body, the fluorene structural units that use contains the alkoxyl group replacement can improve the electron repulsive ability that dyestuff divides to body, the use of fluorenes unit simultaneously also can reduce molecular aggregates, reduce the electron recombination in battery, effectively improve the open circuit voltage of battery, alkyl chain be introduced in the solvability that can improve dyestuff when reducing molecular aggregates, for device optimization facilitates.Provided by the invention take contain alkoxyl group substituted fluorene unit three arylamine as the synthetic route of the organic dye to body is easy, be easy to purifying; By dye-sensitized solar cells prepared by organic dye of the present invention, open circuit voltage reaches 948 millivolts, and short-circuit photocurrent reaches 14.36 milliamperes every square centimeter, and power-conversion efficiencies reaches 9.9 %.
Embodiment
Below in conjunction with specific embodiment, technical solution of the present invention is done to further detailed description.
Reagent used in the embodiment of the present invention all can obtain by being purchased mode.
Embodiment 1: take and contain the preparation of three arylamine of alkoxyl group substituted fluorene unit as the organic dye to body (I)
Synthetic route is as follows:
Synthesizing of intermediate 2:
In reaction flask, add 0.600 to digest compound 1, 0.480 gram 4-hexyloxy-N-phenylaniline, be dissolved in 10 milliliters of toluene, under argon shield, add successively 0.014 gram three (dibenzalacetone) two palladiums, 0.017 gram 4, the two diphenylphosphines-9 of 5-, 9-dimethyl oxa-anthracene (Xantphos) and 0.290 gram sodium tert-butoxide, under argon gas atmosphere, back flow reaction is 12 hours, stopped reaction, be cooled to room temperature, with ethyl acetate and water extraction, separate organic phase, use anhydrous sodium sulfate drying, filter, concentrated filtrate, with methylene dichloride/sherwood oil (volume ratio 1/10) as the developping agent column chromatography, obtain 0.835 gram intermediate 2, yield 95%,
Synthesizing of intermediate 3:
In reaction flask, add 0.590 gram intermediate 2 and 50 milliliters of ethanol, be heated to 60 degrees centigrade, add 0.130 gram iodine, 0.040 gram Periodic acid, under 60 degrees centigrade, reaction is 5 hours, stopped reaction, be cooled to room temperature, ethyl acetate extraction, wash organic phase with saturated sodium thiosulfate solution and sodium chloride aqueous solution, use the anhydrous sodium sulfate drying organic phase, filter, concentrated filtrate, use ethyl acetate/petroleum ether (volume ratio 1/100) as the developping agent column chromatography, obtain 0.687 gram intermediate 3, yield 96%;
Synthesizing of intermediate 4:
In reaction flask, add 0.573 gram intermediate 3, be dissolved in 15 milliliters of methyl-sulphoxides, under argon shield, add 0.059 gram [two (diphenylphosphine) ferrocene of 1,1'-] palladium chloride (Pd (dppf) Cl
2), 0.305 gram duplex tetramethyl ethylene ketone boric acid ester, 0.235 gram Potassium ethanoate, reaction is 20 hours under 50 degrees centigrade, and stopped reaction, be cooled to room temperature, ethyl acetate and water extraction, separate organic phase, use the anhydrous sodium sulfate drying organic phase, filter, concentrated filtrate, by ethyl acetate/petroleum ether (volume ratio 1/100), as the developping agent column chromatography, obtain 0.452 gram intermediate 4, yield 79%;
Synthesizing of intermediate 5:
In reaction flask, add 0.207 gram 6-bromo-4, the two dodecyls of 4--4H-cyclopentano [2, 1-b:3, 4-b '] two thiophene-2-formaldehydes and 0.286 gram intermediate 4, be dissolved in 15 milliliters of tetrahydrofuran (THF)/water (volume ratio 5/1) mixed solvent, under argon shield, add 0.002 gram palladium, 0.004 gram SPhos, 0.352 gram potassiumphosphate, at room temperature reacted 6 hours, stopped reaction, ethyl acetate and water extraction, separate organic phase, use the anhydrous sodium sulfate drying organic phase, filter, concentrated filtrate, by ethyl acetate/petroleum ether (volume ratio 1/50) as the developping agent column chromatography, obtain 0.316 gram intermediate 5, yield 84%,
Take three arylamine that contain alkoxyl group substituted fluorene unit as the organic dye to body (I) synthetic:
In reaction flask, add 0.253 gram intermediate 5 and 0.056 gram cyanoacetic acid, with 15 milliliters of chloroforms, all dissolve, under argon shield; add 0.115 milliliter of piperidines; back flow reaction 16 hours, stopped reaction, be cooled to room temperature; system is with the aqueous hydrochloric acid acidifying of 2 moles every liter 2 times; organic phase washes with water 2 times, and concentrated, ethanol/methylene (volume ratio 1/10) is as the developping agent column chromatography; obtain 0.222 gram organic dye (I), yield reaches 83%.
Take three arylamine that the contain alkoxyl group substituted fluorene unit nuclear-magnetism characterization data as the organic dye to body (I):
1H NMR (400 MHz, THF-d
8) δ: 8.49 (s, 1H), 7.92 (s, 1H), 7.73-7.67 (m, 4H), 7.52 (s, 1H), 7.30 (d, J=1.6 Hz, 1H), 7.25 (d, J=8.8 Hz, 2H), 7.18 (d, J=8.8 Hz, 2H), 7.16 (dd, J=8.8 Hz, J=2.0 Hz, 2H), 7.06-7.00 (m, 4H), 4.16 (m, 4H), 2.11 (m, 8H), 1.95 (m, 4H), 1.75 (m, 4H), 1.55 (m, 8H), 1.48-1.33 (m, 36H), 1.15 (m, 4H), 1.10 (t, J=6.8 Hz, 6H), 1.04 (t, J=6.8 Hz, 6H), 0.52 (t, J=7.2 Hz, 6H).
13C NMR(100 MHz, THF-d
8) δ: 165.29, 165.14, 160.60, 158.92, 157.65, 152.82, 151.07, 150.34, 150.16, 147.75, 147.20, 141.64, 138.81, 137.82, 135.50, 135.03, 132.59, 128.51, 128.24, 127.50, 124.86, 122.78, 121.03, 120.76, 120.46, 117.94, 116.56, 114.27, 110.55, 96.62, 69.21, 57.37, 55.39, 39.16, 33.98, 33.31, 33.07, 31.41, 31.03, 30.89, 30.75, 27.26, 24.01, 14.90, 14.86, 9.37.
Embodiment 2: take and contain the preparation of three arylamine of alkoxyl group substituted fluorene unit as the organic dye to body (II)
Synthetic route is as follows:
Synthesizing of intermediate 2:
In reaction flask, add 3.000 to digest compound 1,0.27 milliliter aniline, be dissolved in 40 milliliters of toluene, under argon shield, add successively 0.046 gram three (dibenzalacetone) two palladiums, 0.052 gram Xantphos and 0.870 gram sodium tert-butoxide, under argon gas atmosphere, back flow reaction is 10 hours, stopped reaction, be cooled to room temperature, with ethyl acetate and water extraction, separate organic phase, use the anhydrous sodium sulfate drying organic phase, filter, concentrated filtrate, use ethyl acetate/petroleum ether (volume ratio 1/50) as the developping agent column chromatography, obtain 2.360 gram intermediates 2, yield 95%;
Synthesizing of intermediate 3:
In reaction flask, add 0.734 gram intermediate 2 and 50 milliliters of ethanol, be heated to 60 degrees centigrade, add 0.130 gram iodine, 0.040 gram Periodic acid, under 60 degrees centigrade, reaction is 5 hours, stopped reaction, be cooled to room temperature, ethyl acetate extraction, wash organic phase with saturated sodium thiosulfate solution and sodium chloride aqueous solution, use the anhydrous sodium sulfate drying organic phase, filter, concentrated filtrate, use ethyl acetate/petroleum ether (volume ratio 1/100) as the developping agent column chromatography, obtain 0.834 gram intermediate 3, yield 97%;
Synthesizing of intermediate 4:
In reaction flask, add 0.430 gram intermediate 3, be dissolved in 15 milliliters of methyl-sulphoxides, under argon shield, add 0.037 gram Pd (dppf) Cl
2, 0.256 gram duplex tetramethyl ethylene ketone boric acid ester, 0.147 gram Potassium ethanoate, reaction is 20 hours under 50 degrees centigrade, and stopped reaction, be cooled to room temperature, ethyl acetate and water extraction, separate organic phase, use the anhydrous sodium sulfate drying organic phase, filter, concentrated filtrate, by ethyl acetate/petroleum ether (volume ratio 1/100), as the developping agent column chromatography, obtain 0.284 gram intermediate 4, yield 66%;
Synthesizing of intermediate 5:
In reaction flask, add 0.124 gram 6-bromo-4, the two dodecyls of 4--4H-cyclopentano [2, 1-b:3, 4-b '] two thiophene-2-formaldehydes and 0.210 gram intermediate 4, be dissolved in 15 milliliters of tetrahydrofuran (THF)/water (volume ratio 5/1) mixed solvent, under argon shield, add 0.002 gram palladium, 0.004 gram SPhos, 0.352 gram potassiumphosphate, at room temperature reacted 6 hours, stopped reaction, ethyl acetate and water extraction, separate organic phase, use the anhydrous sodium sulfate drying organic phase, filter, concentrated filtrate, by ethyl acetate/petroleum ether (volume ratio 1/50) as the developping agent column chromatography, obtain 0.212 gram intermediate 5, yield 83%,
Take three arylamine that contain alkoxyl group substituted fluorene unit as the organic dye to body (II) synthetic:
In reaction flask, add 0.184 gram intermediate 5 and 0.037 gram cyanoacetic acid, with 15 milliliters of chloroforms, all dissolve, under argon shield; add 0.077 milliliter of piperidines; back flow reaction 16 hours, stopped reaction, be cooled to room temperature; system is with the aqueous hydrochloric acid acidifying of 2 moles every liter 2 times; organic phase washes with water 2 times, and concentrated, ethanol/methylene (volume ratio 1/10) is as the developping agent column chromatography; obtain 0.166 gram organic dye (II), yield reaches 86%.
Take three arylamine that the contain alkoxyl group substituted fluorene unit nuclear-magnetism characterization data as the organic dye to body (II):
1H NMR (400 MHz, THF-d
8) δ: 8.50 (s, 1H), 7.92 (s, 1H), 7.77-7.70 (m, 6H), 7.55 (s, 1H), 7.33-7.24 (m, 6H), 7.03 (m, 4H), 4.18 (t, J=6.4 Hz, 4H), 2.09 (m, 12H), 1.96 (m, 4H), 1.63 (m, 4H), 1.55 (m, 8H), 1.48-1.34 (m, 36H), 1.18 (m, 4H), 1.10 (t, J=6.8 Hz, 6H), 1.05 (t, J=7.2 Hz, 6H), 0.52 (t, J=7.2 Hz, 12H).
13C NMR(100 MHz, THF-d
8) δ: 165.24, 160.67, 158.99, 152.79, 152.06, 151.76, 150.20, 149.92, 147.73, 147.24, 139.06, 137.95, 135.53, 135.26, 132.57, 129.27, 127.54, 125.08, 124.09, 121.10, 120.79, 120.72, 118.17, 117.94, 114.30, 110.55, 96.62, 69.21, 57.44, 55.42, 39.18, 34.07, 33.32, 33.14, 31.43, 31.04, 30.90, 30.76, 27.28, 24.02, 14.86, 9.44.
Embodiment 3: take and contain the preparation of three arylamine of alkoxyl group substituted fluorene unit as the organic dye to body (III)
Synthetic route is as follows:
Synthesizing of intermediate 2:
In reaction flask, add 1.400 to digest compound 1, 0.170 milliliter benzamide, be dissolved in 40 milliliters of toluene, under argon shield, add successively 0.042 gram three (dibenzalacetone) two palladiums, 0.049 gram Xantphos and 0.670 gram sodium tert-butoxide, under argon gas atmosphere, back flow reaction is 10 hours, stopped reaction, be cooled to room temperature, with ethyl acetate and water extraction, separate organic phase, distillate solvent, the aqueous sodium hydroxide solution that adds 10 milliliters of ethanol and 10 milliliters 2 moles every liter, be heated to 80 degrees centigrade of reactions 10 hours, be cooled to room temperature, with ethyl acetate and water extraction, separate organic phase, use the anhydrous sodium sulfate drying organic phase, filter, concentrated filtrate, with methylene dichloride/sherwood oil (volume ratio 1/5) as the developping agent column chromatography, obtain 0.400 gram intermediate 2, yield 43%,
Synthesizing of intermediate 3:
In reaction flask, add 0.400 gram intermediate 2 and 0.668 gram 9, 9-diethyl-2, the iodo-9H-fluorenes of 7-bis-, be dissolved in 20 milliliters of toluene, under argon shield, add successively 0.022 gram three (dibenzalacetone) two palladiums, 0.022 gram Xantphos and 0.120 gram sodium tert-butoxide, under argon gas atmosphere, back flow reaction is 10 hours, stopped reaction, be cooled to room temperature, with ethyl acetate and water extraction, separate organic phase, use the anhydrous sodium sulfate drying organic phase, filter, concentrated filtrate, with methylene dichloride/sherwood oil (volume ratio 1/10) as the developping agent column chromatography, obtain 0.300 gram intermediate 2, yield 49%,
Synthesizing of intermediate 4:
In reaction flask, add 0.230 gram intermediate 3, be dissolved in 15 milliliters of methyl-sulphoxides, under argon shield, add 0.016 gram Pd (dppf) Cl
2, 0.113 gram duplex tetramethyl ethylene ketone boric acid ester, 0.067 gram Potassium ethanoate, reaction is 20 hours under 50 degrees centigrade, and stopped reaction, be cooled to room temperature, ethyl acetate and water extraction, separate organic phase, use the anhydrous sodium sulfate drying organic phase, filter, concentrated filtrate, by ethyl acetate/petroleum ether (volume ratio 1/100), as the developping agent column chromatography, obtain 0.124 gram intermediate 4, yield 54%;
Synthesizing of intermediate 5:
In reaction flask, add 0.052 gram 6-bromo-4, the two dodecyls of 4--4H-cyclopentano [2, 1-b:3, 4-b '] two thiophene-2-formaldehydes and 0.100 gram intermediate 4, be dissolved in 10 milliliters of tetrahydrofuran (THF)/water (volume ratio 5/1) mixed solvent, under argon shield, add 0.002 gram palladium, 0.004 gram SPhos, 0.088 gram potassiumphosphate, at room temperature reacted 6 hours, stopped reaction, ethyl acetate and water extraction, separate organic phase, use the anhydrous sodium sulfate drying organic phase, filter, concentrated filtrate, by ethyl acetate/petroleum ether (volume ratio 1/50) as the developping agent column chromatography, obtain 0.086 gram intermediate 5, yield 73%,
Take three arylamine that contain alkoxyl group substituted fluorene unit as the organic dye to body (III) synthetic:
In reaction flask, add 0.070 gram intermediate 5 and 0.037 gram cyanoacetic acid, with 15 milliliters of chloroforms, all dissolve, under argon shield; add 0.077 milliliter of piperidines; back flow reaction 16 hours, stopped reaction, be cooled to room temperature; system is with the aqueous hydrochloric acid acidifying of 2 moles every liter 2 times; organic phase washes with water 2 times, and concentrated, ethanol/methylene (volume ratio 1/10) is as the developping agent column chromatography; obtain 0.057 gram organic dye (III), yield reaches 78%.
Take three arylamine that the contain alkoxyl group substituted fluorene unit nuclear-magnetism characterization data as the organic dye to body (III):
1H NMR (400 MHz, THF-d
8) δ: 8.51 (s, 1H), 7.94 (s, 1H), 7.85 (m, 3H), 7.80 (d, J=8.4 Hz, 1H), 7.73-7.68 (m, 5H), 7.37 (m, 3H), 7.25 (m, 3H), 7.03 (m, 4H), 4.18 (t, J=6.4 Hz, 4H), 2.09 (m, 16H), 1.96 (m, 4H), 1.69 (m, 4H), 1.56 (m, 8H), 1.48-1.34 (m, 36H), 1.20 (m, 4H), 1.11 (t, J=7.2 Hz, 6H), 1.04 (t, J=6.8 Hz, 6H), 0.54 (m, 18H).
13C NMR(100 MHz, THF-d
8) δ: 165.17, 160.56, 159.11, 152.68, 152.46, 151.86, 150.01, 149.81, 147.88, 147.76, 143.48, 138.57, 138.13, 136.66, 135.75, 135.64, 134.01, 132.69, 126.16, 124.80, 123.74, 121.87, 121.01, 120.74, 120.29, 118.98, 117.91, 114.26, 110.55, 96.62, 69.20, 57.58, 57.40, 55.50, 39.20, 34.13, 33.31, 33.14, 31.44, 31.04, 30.91, 30.75, 27.28, 24.01, 14.89, 9.57, 9.50.
Embodiment 4
By nano-TiO
2Structure duplicature electrode be immersed in acetonitrile/trimethyl carbinol of containing every liter of dyestuff of 100 micromole (I) (volume ratio, 1:1) in solution 12 hours, then by spin coating the glass electrode of Platinum Nanoparticles by the heat of 35 micron thick, melt ring and TiO
2The sealing of structure duplicature heated by electrodes, finally be injected into ionogen in the gap of two electrodes, namely formed dye-sensitized solar cells.The dye-sensitized solar cells performance structure that test obtains is as shown in table 1.
Embodiment 5
By nano-TiO
2Structure duplicature electrode be immersed in acetonitrile/trimethyl carbinol of containing every liter of dyestuff of 100 micromole (II) (volume ratio, 1:1) in solution 12 hours, then by spin coating the glass electrode of Platinum Nanoparticles by the heat of 35 micron thick, melt ring and TiO
2The sealing of structure duplicature heated by electrodes, finally be injected into ionogen in the gap of two electrodes, namely formed dye-sensitized solar cells.The dye-sensitized solar cells performance structure that test obtains is as shown in table 1.
Embodiment 6
By nano-TiO
2Structure duplicature electrode be immersed in acetonitrile/trimethyl carbinol of containing every liter of dyestuff of 100 micromole (III) (volume ratio, 1:1) in solution 12 hours, then by spin coating the glass electrode of Platinum Nanoparticles by the heat of 35 micron thick, melt ring and TiO
2The sealing of structure duplicature heated by electrodes, finally be injected into ionogen in the gap of two electrodes, namely formed dye-sensitized solar cells.The dye-sensitized solar cells performance structure that test obtains is as shown in table 1.
Table 1
Claims (4)
- Claim 1~2 any one describedly take three arylamine that contain alkoxyl group substituted fluorene unit and be the application of the organic dye to body in dye-sensitized solar cells.
- 4. an organic dye sensitized solar cell, is characterized in that, dye coating be claim 1~2 any one describedly take three arylamine that contain alkoxyl group substituted fluorene unit and be the organic dye to body.
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CN101407639A (en) * | 2008-11-24 | 2009-04-15 | 中国科学院长春应用化学研究所 | Organic dye with five-element heterocycle and derivative thereof as conjugate unit, and dye sensitization solar cell prepared thereby |
CN102702075A (en) * | 2012-06-13 | 2012-10-03 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent material containing tertiary aromatic amine structure and preparation method and application thereof |
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CN101407639A (en) * | 2008-11-24 | 2009-04-15 | 中国科学院长春应用化学研究所 | Organic dye with five-element heterocycle and derivative thereof as conjugate unit, and dye sensitization solar cell prepared thereby |
CN102702075A (en) * | 2012-06-13 | 2012-10-03 | 吉林奥来德光电材料股份有限公司 | Organic electroluminescent material containing tertiary aromatic amine structure and preparation method and application thereof |
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