CN102898859B - Organic dye and application thereof in dye-sensitized solar cell - Google Patents
Organic dye and application thereof in dye-sensitized solar cell Download PDFInfo
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- CN102898859B CN102898859B CN2012104013779A CN201210401377A CN102898859B CN 102898859 B CN102898859 B CN 102898859B CN 2012104013779 A CN2012104013779 A CN 2012104013779A CN 201210401377 A CN201210401377 A CN 201210401377A CN 102898859 B CN102898859 B CN 102898859B
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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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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/542—Dye sensitized solar cells
Abstract
The invention provides organic dye and the application of the organic dye in a dye-sensitized solar cell, belonging to the field of organic dye. The organic dye takes N-biphenyl substituted di-thienopyridine as a conjugate unit, and takes a thienopyridine structure unit as an electron-rich structure unit, so that the dye is better in optical absorptivity; and a N atom is connected with a long alkyl chain, so that the gathering of the dye can be preferably reduced, and the photovoltage of a device can be improved. The organic dye provided by the invention is simple in synthesis process, low in raw material cost, high in reaction yield, and easy to purify. According to the dye-sensitized solar cell prepared by the organic dye provided by the invention, the high voltage of 960 millivolts and the short-circuit current density of 13.53 milliamperes/ square centimeter can be achieved, and the power conversion efficiency reaches 9.3%.
Description
Technical field
The present invention relates to the organic dye technical field, be specifically related to a kind of organic dye and the application in dye-sensitized solar cells.
Background technology
Among renewable energy source, sun power is a kind of ideal clean energy, and by solar cell, carrying out opto-electronic conversion is one of main path of human use's sun power.In the solar cell field, high and technology maturation has occupied the larger market share to silicon solar cell because of its turnover ratio, but the prices of raw and semifnished materials of silicon solar cell are expensive, production cost is high, its photoelectric transformation efficiency is difficult to further lifting simultaneously, and these defects have seriously limited the development of silicon solar cell.The senior engineer's of Swiss Confederation in 1991
Professor has reported efficient dye-sensitized solar cells (Nature, 1991,353,737), and through vicennial development, current dye-sensitized solar cells has approached the photoelectric transformation efficiency of silion cell.What is more important, the manufacturing cost of dye-sensitized solar cells are only 1/10 of silion cell, have a good application prospect, and likely in future, replace silion cell and occupy the market of solar cell.At present, be total to dye-sensitized solar cells prepared by sensitization with organic dye Y123 and zinc protoporphyrin dyestuff YD2-o-C8, obtained 12.3% photoelectric transformation efficiency (Science, 2011,334,629).Wherein, the dependence of the solar cell of high efficiency dye sensitization in the past to many pyridines of precious metal ruthenium dye broken away from the use of organic dye, reduced largely the cost of battery.With the [Ru(bpy)2(dppzi) dyestuff, compare, the selection of organic dye is more various, and its starting material source is abundant, and structure is cut out flexibly, and preparation cost is cheap, has high DEVELOPMENT PROSPECT.
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, and a kind of organic dye and the application in dye-sensitized solar cells are provided.
The invention provides a kind of organic dye, structure is as shown in formula I:
In formula I, R
1, R
2Independent separately is hydrogen atom, C
1～C
18Alkyl or C
1～C
18Alkoxyl group; R
3For C
1～C
18Alkyl or C
1～C
18Alkoxyl group.
Preferably, described organic dye has the structure shown in formula II:
The invention provides the application of the described organic dye of a kind of technique scheme in dye-sensitized solar cells.
The present invention also provides a kind of organic dye sensitized solar cell, and dye coating is the described organic dye of technique scheme.
Beneficial effect
The invention provides a kind of organic dye and the application in dye-sensitized solar cells.This organic dye has the formula I structure, to using N-biphenyl replacement two Thienopyrroles as conjugate unit, the Thienopyrroles structural unit is the electron rich structural unit, make dyestuff have better light absorpting ability, simultaneously, on the N atom, connect long alkyl chain, help to reduce the gathering of dyestuff, improve the photovoltage of device.Organic dye synthesis technique of the present invention is simple, material cost is low, reaction yield is high, be easy to purifying, the dye-sensitized solar cells prepared by organic dye of the present invention, can reach the high-voltage of 960 millivolts and the short-circuit current density of 13.53 milliamperes every square centimeter, power conversion efficiency has reached 9.3%.
The accompanying drawing explanation
Fig. 1 is the dye-sensitized solar cells photoelectric transformation efficiency of the embodiment of the present invention 2 preparations and the graphic representation of wavelength;
Fig. 2 is dye-sensitized solar cells electric current and the voltage curve figure of the embodiment of the present invention 2 preparations.
Embodiment
Below in conjunction with specific embodiment, technical solution of the present invention is done to further detailed description.
The material of mentioning in embodiment all can obtain by being purchased mode.
Embodiment 1: the organic dye of chemical structure formula II is synthetic
Synthesizing of intermediate 2:
In 500 milliliters of three mouthfuls of reaction flasks, add 10 gram raw material 1,29 gram salt of wormwood and 200 milliliters of acetone, oil pump vacuumizes ventilation, under argon shield, add 32 gram n-octane bromides, obtain mixture, by said mixture reflux cool to room temperature after 12 hours, add 200 ml water termination reactions, reaction soln is by the organic phase dried over sodium sulfate obtained after chloroform extraction, filter, decompression is revolved and except the crude product obtained after filtrate, is usingd sherwood oil and with the silica gel chromatography column chromatography, obtain 18.7 gram intermediates 2 as eluent, and reaction yield is 96%;
The nuclear-magnetism characterization data of intermediate 2:
1HNMR(600MHz,DMSO-d
6)δ:7.24(t,J=8.4Hz,1H),6.58(d,J=8.4Hz,2H),3.99(t,J=6.6Hz,4H),1.71(m,4H),1.47(m,4H),1.26(m,16H),0.86(t,J=7.2Hz,6H)；
13CNMR(150MHz,DMSO-d
6)δ:158.42,129.93,105.26,78.67,68.62,31.16,28.62,28.56,25.52,22.03,13.91；
Synthesizing of intermediate 3:
In 250 milliliters of three mouthfuls of reaction flasks, add 2 gram intermediates 2, 0.8 gram p-aminophenyl pinacol boric acid ester and 3.8 gram potassiumphosphates, add 90 milliliter 1, 4-dioxane and 18 ml waters, oil pump vacuumizes ventilation, under argon shield, add 30 milligrams of 2-dicyclohexyl phosphorus-2', 6'-dimethoxy-biphenyl (SPhos) and 16 milligrams of palladium, by said mixture cool to room temperature after stirring 24 hours under 45 ℃, use ethyl acetate extraction, organic phase is with after dried over sodium sulfate, filtering, decompression is revolved and with methylene dichloride and sherwood oil (volume ratio 2:1), with the silica gel chromatography column chromatography, is obtained 1.57 gram intermediates 3 as eluent except the crude product obtained after filtrate, reaction yield is 85%,
The nuclear-magnetism characterization data of intermediate 3:
1HNMR(600MHz,DMSO-d
6)δ:7.12(t,J=8.4Hz,1H),6.91(d,J=8.4Hz,2H),6.63(d,J=8.4Hz,2H),6.51(d,J=8.4Hz,2H),4.94(s,2H),3.83(t,J=6.6Hz,4H),1.52(m,4H),1.27(m,4H),1.22(m,16H),0.86(t,J=7.2Hz,6H)；
13CNMR(150MHz,DMSO-d
6)δ:156.69,146.79,131.34,127.50,120.91,120.00,112.70,105.56,67.73,31.14,28.63,28.47,25.35,22.04,13.92；
Synthesizing of intermediate 4:
In 25 milliliters of three mouthfuls of reaction flasks, add 0.19 gram 3,3 '-dibromo (2,2 '-bithiophene) and 5 milliliters of toluene, oil pump vacuumizes ventilation, under argon shield, adds successively 0.13 gram sodium tert-butoxide, 13 milligram three (dibenzalacetone) two palladium (Pd
2(dba)
3) and 36 milligrams (±)-2,2'-is two-(diphenyl phosphine)-1, and 1'-dinaphthalene (BINAP) at room temperature stirs said mixture after 30 minutes and adds 0.25 gram intermediate 3, and reflux adds 5 ml water termination reactions after 20 hours.The solution ethyl acetate extraction, organic phase is with after dried over sodium sulfate, filtering, decompression is revolved and with methylene dichloride and sherwood oil (volume ratio 1:2), with the silica gel chromatography column chromatography, is obtained 0.33 gram intermediate 4 as eluent except the crude product obtained after solution, and reaction yield is 85%;
The characterization data of intermediate 4:
1HNMR(600MHz,DMSO-d
6)δ:7.62(d,J=8.4Hz,2H),7.47(m,4H),7.30(d,J=5.4Hz,2H),7.26(t,J=8.4Hz,1H),6.73(d,J=8.4Hz,2H),3.92(t,J=6.6Hz,4H),1.55(m,4H),1.25(m,4H),1.13(m,16H),0.71(t,J=6.6Hz,6H)；
13CNMR(150MHz,DMSO-d
6)δ:156.59,143.26,137.13,132.48,131.76,129.02,124.58,120.43,118.44,116.22,112.43,105.62,68.05,31.09,28.65,28.56,25.44,21.97,13.74；
Synthesizing of intermediate 5:
In 25 milliliters of three mouthfuls of reaction flasks, add 0.47 gram intermediate 4, 0.174 milliliter N, N '-dimethyl formamide (DMF) and 10 milliliter 1, the 2-ethylene dichloride, be cooled to-10 ℃, slowly drip 0, 09 milliliter of phosphorus oxychloride, drip end afterreaction system and rose to stirring at room 10 hours, add 20 milliliters of saturated sodium acetate aqueous solutions, stirring at room 4 hours, the reaction soln dichloromethane extraction, organic phase is with after dried over sodium sulfate, filtering, decompression is revolved and with methylene dichloride and sherwood oil (volume ratio 2:1), with the silica gel chromatography column chromatography, is obtained 0.45 gram intermediate 5 as eluent except the crude product obtained after filtrate, reaction yield is 91%,
The nuclear-magnetism characterization data of intermediate 5:
1HNMR(600MHz,DMSO-d
6)δ:9.92(s,1H),8.26(s,1H),7.78(d,J=5.4Hz,1H),7.69(d,J=8.4Hz,2H),7.50(d,J=8.4Hz,2H),7.37(d,J=5.4Hz,1H),7.28(t,J=8.4Hz,1H),6.75(d,J=8.4Hz,2H),3.93(t,J=6.0Hz,4H),1.55(m,4H),1.24(m,4H),1.10(m,16H),0.68(t,J=7.2Hz,6H)；
13CNMR(150MHz,DMSO-d
6)δ:184.16,156.58,147.22,142.15,140.32,136.24,132.58,130.40,129.13,123.71,122.97,120.88,118.38,116.43,112.32,105.68,68.12,31.07,28.62,28.56,25.41,21.94,13.68；
Synthesizing of intermediate 6:
In 25 milliliters of three mouthfuls of reaction flasks, add 0.2 gram intermediate 5 and 15 milliliters of tetrahydrofuran (THF)s, be cooled to 0 ℃, oil pump vacuumizes ventilation, under argon shield, add 58 milligrams of bromo-succinimides (NBS), the reaction system lucifuge stirs after 24 hours and adds 20 milliliters of acetone termination reactions, the crude product that decompression obtains after revolving and desolventizing obtains 0.19 gram intermediate 6 as eluent with the silica gel chromatography column chromatography with methylene dichloride and sherwood oil (volume ratio 2:1), and reaction yield is 85%;
The nuclear-magnetism characterization data of intermediate 6:
1HNMR(400MHz,DMSO-d
6)δ:9.92(s,1H),8.23(s,1H),7.68(d,J=8.4Hz,2H),7.54(s,1H),7.48(d,J=8.4Hz,2H),7.28(t,J=8.4Hz,1H),6.75(d,J=8.4Hz,2H),3.93(t,J=6.0Hz,4H),1.55(m,4H),1.23(m,4H),1.17(m,16H),0.69(t,J=7.2Hz,6H)；
13CNMR(150MHz,CDCl
3)δ:182.94,157.13,145.68,142.58,140.88,136.38,133.67,133.00,129.05,124.35,121.57,120.90,118.69,116.64,115.75,115.66,105.34,68.64,31.75,29.26,29.17,29.10,26.00,22.59,14.01；
Synthesizing of intermediate 7:
In 25 milliliters of three mouthfuls of reaction flasks, add 0.15 gram intermediate 6, 0.15 gram two hexyloxy replace triphenylamine tetramethyl ethylene ketone boric acid ester, 0.23 gram potassiumphosphate, 5 milliliter 1, 4-dioxane and 1 ml water, oil pump vacuumizes ventilation, under argon shield, add 2 milligrams of 2-dicyclohexyl phosphorus-2', 6'-dimethoxy-biphenyl (SPhos) and 1 milligram of palladium, the said mixture stirring at room was used to ethyl acetate extraction after 24 hours, organic phase is with after dried over sodium sulfate, filtering, decompression is revolved and with methylene dichloride and sherwood oil (volume ratio 2:1), with the silica gel chromatography column chromatography, is obtained 0.2 gram intermediate 7 as eluent except the crude product obtained after filtrate, reaction yield is 90%,
The nuclear-magnetism characterization data of intermediate 7:
1HNMR(400MHz,DMSO-d
6)δ:9.89(s,1H),8.21(s,1H),7.72(d,J=8.4Hz,2H),7.56(m,3H),7.49(d,J=8.4Hz,2H),7.28(t,J=8.4Hz,1H),7.04(d,J=8.8Hz,4H),6.91(d,J=8.8Hz,4H),6.76(m,4H),3.93,(m,8H),1.68(m,4H),1.55(m,4H),1.41(m,4H),1.31(m,8H),1.18,(m,12H),1.08(m,8H),0.87(t,J=7.2Hz,6H),0.66(t,J=6.6Hz,6H).
13CNMR(100MHz,CDCl
3)δ:182.72,157.15,155.84,149.05,148.76,148.39,142.88,140.08,139.92,136.87,133.13,132.88,128.97,126.90,126.39,126.24,125.44,121.60,120.81,119.88,118.82,115.34,114.81,106.32,105.35,68.64,68.26,31.73,31.59,29.70,29.30,29.24,29.15,29.08,25.97,25.75,22.59,14.01；
Synthesizing of the organic dye of chemical structure formula II:
In 50 milliliters of three mouthfuls of reaction flasks, add the bold and unconstrained gram cyanoacetic acid of 0.2 gram intermediate 7,48 and 10 milliliters of chloroforms; under argon shield, add 0.13 milliliter of piperidines; said mixture is warming up to back flow reaction and after 12 hours, is cooled to room temperature; with the hydrochloric acid soln of 2 moles every liter, be acidified to pH=1; the reaction mixture chloroform extraction; organic phase is with after anhydrous sodium sulfate drying, filtering; decompression is revolved and with methyl alcohol and chloroform (volume ratio 1:50), as eluent, is obtained the organic dye of chemical structure formula II with the silica gel chromatography column chromatography except the crude product obtained after filtrate, and reaction yield is 89%.
The nuclear-magnetism characterization data of the organic dye of chemical structure formula II:
1HNMR(400MHz,DMSO-d
6)δ:13.38(s,1H),8.51(s,1H),8.22(s,1H),7.70(d,J=8.4Hz,2H),7.54(m,3H),7.48(d,J=8.4Hz,2H),7.25(t,J=8.4Hz,1H),7.04(d,J=8.8Hz,4H),6.90(d,J=8.8Hz,4H),6.75(m,4H),3.93,(m,8H),1.70(m,4H),1.57(m,4H),1.41(m,4H),1.31(m,8H),1.15,(m,20H),0.86(t,J=7.2Hz,6H),0.66(t,J=6.6Hz,6H).
13CNMR(100MHz,CDCl
3)δ:168.99,157.12,155.91,150.51,150.22,149.29,148.54,143.63,139.91,136.54,133.34,133.03,132.76,128.96,128.42,126.97,126.44,125.82,122.03,121.49,119.61,118.69,116.78,115.35,115.01,106.02,105.30,91.98,68.63,68.26,31.73,31.59,29.69,29.30,29.24,29.15,29.06,25.96,25.74,22.58,14.01.
Embodiment 2: dye-sensitized solar cells prepared by the organic dye of chemical structure formula II
By TiO
2Structure duplicature electrode is immersed in the mixing solutions of the acetonitrile that contains every liter of dyestuff of 150 micromole (II) and the trimethyl carbinol (volume ratio is 1:1) 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 two gaps between electrode, namely formed dye-sensitized solar cells.Fig. 1 is the dye-sensitized solar cells photoelectric transformation efficiency of the embodiment of the present invention 2 preparations and the graphic representation of wavelength; Fig. 2 is dye-sensitized solar cells electric current and the voltage curve figure of the embodiment of the present invention 2 preparations.The dye-sensitized solar cells performance structure that test obtains is as shown in table 1.
Table 1
Claims (3)
1. an organic dye, is characterized in that, described organic dye has the structure shown in formula II:
2. the application of a kind of organic dye claimed in claim 1 in dye-sensitized solar cells.
3. an organic dye sensitized solar cell, is characterized in that, dye coating is a kind of organic dye claimed in claim 1.
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| CN103554958A (en) * | 2013-11-08 | 2014-02-05 | 天津理工大学 | Dithiophene pyrrole bridge-indoline organic dyes as well as preparation method and application thereof |
| CN111253774A (en) * | 2020-03-25 | 2020-06-09 | 大连理工大学 | Dithienopyrrole functional dye containing phenoxy long carbon chain and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6245988B1 (en) * | 1997-05-07 | 2001-06-12 | Ecole Polytechnique Federale De Lausanne | Metal complex photosensitizer and photovoltaic cell |
| CN101497746A (en) * | 2009-03-05 | 2009-08-05 | 中国科学院长春应用化学研究所 | Organic dye containing thiophen ethylene and dye sensitization solar cell prepared thereby |
| WO2012102544A2 (en) * | 2011-01-28 | 2012-08-02 | 주식회사 동진쎄미켐 | Novel organic dye and a production method therefor |
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| CN101240117B (en) * | 2008-02-04 | 2010-11-10 | 中国科学院长春应用化学研究所 | Pure organic dyestuff and dyestuff sensitization solar energy battery prepared therefrom |
| WO2011003280A1 (en) * | 2009-07-10 | 2011-01-13 | 国家纳米技术与工程研究院 | Organic dyes and preparation method thereof and dye-sensitized solar cells |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6245988B1 (en) * | 1997-05-07 | 2001-06-12 | Ecole Polytechnique Federale De Lausanne | Metal complex photosensitizer and photovoltaic cell |
| CN101497746A (en) * | 2009-03-05 | 2009-08-05 | 中国科学院长春应用化学研究所 | Organic dye containing thiophen ethylene and dye sensitization solar cell prepared thereby |
| WO2012102544A2 (en) * | 2011-01-28 | 2012-08-02 | 주식회사 동진쎄미켐 | Novel organic dye and a production method therefor |
Non-Patent Citations (1)
| Title |
|---|
| Reduced band gap dithieno[3,2-b : 2 ",3 "-d]pyrroles: New n-type organic materials via unexpected reactivity;Pappenfus, Ted M.，等;《ORGANIC LETTERS》;20080319;第10卷(第8期);1553-1556 * |
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