CN103880834A - Organic solar cell material and preparation method thereof - Google Patents
Organic solar cell material and preparation method thereof Download PDFInfo
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- CN103880834A CN103880834A CN201410077634.7A CN201410077634A CN103880834A CN 103880834 A CN103880834 A CN 103880834A CN 201410077634 A CN201410077634 A CN 201410077634A CN 103880834 A CN103880834 A CN 103880834A
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- diazosulfide
- organic solar
- thiophene
- solar cell
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- 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
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- 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
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
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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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- 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
- Y02E10/549—Organic PV cells
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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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
- Y02P70/50—Manufacturing or production processes characterised by the final manufactured product
Abstract
The invention relates to an organic solar cell material and a preparation method thereof, particularly a novel organic solar cell material based on thiophene-diazosulfide p-n structure and a preparation method thereof. The quantities and contents of the p-type electron donating primitive thiophene and n-type electron receiving primitive diazosulfide are regulated to precisely regulate the band gap of the target material, and the alkyl chain is modified to implement solubility in a polar solvent and application in the field of organic photoelectricity. The structure is disclosed as Formula I. According to the material provided by the invention, Suzuki reaction is utilized to synthesize the monomer, and the material is simple in synthesis technique, easy for mass production and easy to purify. The material has favorable spectrum heat stability, amorphous film-forming stability and narrow optical energy gap, can absorb sunlight within a wider wave spectrum range, and can be used in organic solar cell devices as an active material.
Description
Technical field
The invention belongs to photoelectric material and preparing technical field, be specifically related to a kind of organic solar photoelectric conversion material, is more particularly a kind of novel organic solar cell material based on thiophene-diazosulfide p-n junction structure and preparation method thereof.This material is by regulating quantity and the content of p-type donor residues unit's thiophene and N-shaped acceptor groups unit diazosulfide, carry out the band gap of accuracy controlling target material, and carry out polar functional group modification at its alkyl chain, be widely used in organic electro-optic device, particularly organic solar batteries device.
Background technology
Organic solar batteries (Organic Photo Voltage, OPV) be one of the focus forward position of current scientific research, such device has that snappiness is high, cost of manufacture is low and can obtain the advantages such as Large-Area-Uniform rete, and therefore it is expected to become the novel energy in the fields such as communication, building, traffic, illumination.The principle of work of organic solar batteries generation current is the photovoltaic effect of based semiconductor, in the time that photon incides photochromics, produce electronics and hole pair at material internal, under the effect of built in field, positive pole and negative pole are separately shifted to respectively in electronics and hole, thereby at outer loop generation current.
Organic semiconductor material is widely regarded as the most cheap and the most potential solar cell material, its outstanding advantage embodies a concentrated expression of following several respects: the synthetic cost of (1) organic materials is low, function and structure is easy to modulation, and snappiness and film-forming properties are better; (2) organic solar batteries device fabrication process is relatively simple, can cold operation, and element manufacturing cost is low, is suitable for large-scale promotion application.For obtaining the higher effciency of energy transfer of organic solar batteries, increasing active layer material is designed to be synthesized, especially donor material in recent years.Thiophene-based material is donor material most widely used in organic solar batteries device, the polymkeric substance that comprises polymkeric substance, small molecules, oligomer and contain transition metal etc.Thiophene material is as giving body, C
60or derivative is current best organic solar batteries system as acceptor, and this class material is easy to preparation, and solution processable, has good thermostability, and excellent photoelectric property and carrier transmission characteristics etc., become the focus of people's research.
At present in the organic solar device of open report, the material system of high-photoelectric transformation efficiency is made up of to body and fullerene derivate acceptor thiophene-based.If poly-(3-hexyl thiophene) is (P3HT) the thiophene derivants material of current most study, it can be used as donor material and is widely used in building polymer solar battery material.But also there is obvious deficiency in P3HT, as narrow in spectral absorption scope, be only confined to the absorption of 650nm with interior sunlight, greatly limit the further lifting of solar cell device photoelectric transformation efficiency.Therefore be necessary to optimize the Molecular Structure Design of polythiophene class derivative, further its sunlight spectral response characteristic and absorptive character of modulation, effectively improve the carrier mobility characteristic of polymer donor material simultaneously, develop and there is arrowband gap length absorption, and can have the better efficient organic solar photoelectric conversion material mating with solar spectrum.
Summary of the invention
Technical problem: the organic solar photoelectric conversion material that the object of this invention is to provide a kind of wide absorption, improve the light absorpting ability of thiophene-diazosulfide class organic solar photoelectric conversion material, widen its spectral response range, significantly to improve its photoelectric transformation efficiency.
Technical scheme: the present invention relates to a kind of organic solar battery material and preparation method thereof, is more particularly a kind of novel narrow band gap organic solar battery material based on thiophene-diazosulfide p-n junction structure and preparation method thereof.This body of material is three diazosulfide structural motifs, and two ends, with identical alkylthrophene class formation primitive, are a kind of conjugated structure thiophene-diazosulfide analog derivative materials.Its structure is as shown in the formula shown in I:
Wherein, R is C
1-C
12alkyl;
Based on the novel organic solar cell material of thiophene-diazosulfide p-n junction structure, adopt the two boric acid esters of diazosulfide and bromo thiophene-diazosulfide derivative by Suzuki linked reaction, the novel organic solar cell material of preparation based on thiophene-diazosulfide p-n junction structure, is shown below:
Wherein, R is C
1-C
12alkyl.
This reaction is at tetra-triphenylphosphine palladium (Pd (PPh
3)
4) under katalysis, monomer 1(4 in above formula, two (4,4,5,5-tetramethyl--1,3,2-dioxy boron, penta encircle-2-yl) benzo [c] [1,2, the 5] thiadiazoles of 7-) and monomer 2(bromo thiophene-diazosulfide alkyl-substituted derivative) generation Suzuki linked reaction.
Beneficial effect: the organic solar battery material that the present invention proposes has clear and definite chemical structure, has moderate molecular weight, can be purified and be obtained quite high chemical purity by conventional column chromatography method.Due to the introducing of multiple diazosulfide structural motifs, can effectively reduce the optical energy gap of thiophene-diazosulfide p-n junction structure analog derivative material, widen spectral response range, thereby effectively improve its solar energy photoelectric conversion performance, can be used as acceptor material and be applied to organic solar batteries device.With existing Polythiophene and thiophene diazosulfide polymer phase ratio, there is wider solar spectrum responding range, absorption intensity also strengthens greatly, simultaneously due to the introducing of conjugated structure primitive on side chain, also contributes to improve the carrier transmission characteristics of line style polythiofuran derivative.This molecule material has merged small molecule material and macromolecule polymer material advantage separately, can prepare high performance thin-film device by easy solution film forming mode, has effectively overcome some intrinsic defects of polymer materials.These unique character can be widely used in organic solar batteries device this class novel narrow band gap material.
Brief description of the drawings
Fig. 1 is target material P1 UV and the PL curve in dichloromethane solution obtaining in synthetic example;
Fig. 2 is the MALDI-TOF mass spectrum of the target material P1 that obtains in synthetic example;
Fig. 3 is the target material P1's that obtains in synthetic example
1hNMR figure.
Embodiment
Based on the novel organic solar cell material of thiophene-diazosulfide p-n junction structure, this body of material is three diazosulfide structural motifs, two ends, with identical alkylthrophene class formation primitive, are a kind of conjugated structure thiophene-diazosulfide derivative materials.Its structure is as shown in the formula shown in I:
Embodiment 1:
According to reaction scheme, compound 1 mixes in Hydrogen bromide solvent with bromine, and reaction, obtains compound 2 at 110 DEG C.Be dissolved in Isosorbide-5-Nitrae-dioxane solvent of new steaming 2, with duplex tetramethyl ethylene ketone boric acid ester and potassium acetate, at [1,1 '-bis-(diphenylphosphine) ferrocene] palladium chloride methylene dichloride complex compound (Pd (dppf)
2cl
2) do under the condition of catalyzer and react, obtain compound 3.Compound 4 is dissolved in new steaming tetrahydrofuran solvent, after reacting with butyllithium, adds bromo hexane under the condition of-78 DEG C, obtain compound 5.Be dissolved in new steaming tetrahydrofuran solvent 5, after reacting with n-Butyl Lithium, add Virahol tetramethyl ethylene ketone boric acid ester under the condition of-78 DEG C, obtain 6.By 6 and 2 K at 2mol/mL
2cO
3in solution and toluene solvant, mix, at tetra-triphenylphosphine palladium (Pd (PPh
3)
4) do under the condition of catalyzer Suzuki linked reaction occurs, obtain compound 7.By 7 and 3 K at 2mol/mL
2cO
3in solution and toluene solvant, mix, at tetra-triphenylphosphine palladium (Pd (PPh
3)
4) do under the condition of catalyzer Suzuki linked reaction occurs, make target compound P1.
[reaction scheme]
Embodiment 2:
According to reaction scheme, compound 1 mixes in Hydrogen bromide solvent with bromine, and reaction, obtains compound 2 at 110 DEG C.Be dissolved in Isosorbide-5-Nitrae-dioxane solvent of new steaming 2, with duplex tetramethyl ethylene ketone boric acid ester and potassium acetate, at [1,1 '-bis-(diphenylphosphine) ferrocene] palladium chloride methylene dichloride complex compound (Pd (dppf)
2cl
2) do under the condition of catalyzer and react, obtain compound 3.Compound 4 is dissolved in new steaming tetrahydrofuran solvent, after reacting with butyllithium, adds n-octane bromide under the condition of-78 DEG C, obtain compound 5.Be dissolved in new steaming tetrahydrofuran solvent 5, after reacting with n-Butyl Lithium, add Virahol tetramethyl ethylene ketone boric acid ester under the condition of-78 DEG C, obtain 6.By 6 and 2 K at 2mol/mL
2cO
3in solution and toluene solvant, mix, at tetra-triphenylphosphine palladium (Pd (PPh
3)
4) do under the condition of catalyzer Suzuki linked reaction occurs, obtain compound 7.By 7 and 3 K at 2mol/mL
2cO
3in solution and toluene solvant, mix, at tetra-triphenylphosphine palladium (Pd (PPh
3)
4) do under the condition of catalyzer Suzuki linked reaction occurs, make target compound P2.
[reaction scheme]
Although we are in conjunction with exemplary embodiment, the present invention has been described particularly, but it will be appreciated by those skilled in the art that in the case of not departing from the spirit and scope of the present invention that the claims limit, can make in form and details various modifications and change.
Claims (2)
1. an organic solar battery material, it is characterized in that, this material is based on thiophene-diazosulfide p-n junction structure primitive, main body is three diazosulfide structural motifs, two ends are with identical alkylthrophene class formation primitive, be a kind of conjugated structure thiophene-diazosulfide analog derivative material, its structure is as shown in the formula shown in I:
Wherein, R is C
1-C
12alkyl.
2. the preparation method of an organic solar battery material as claimed in claim 1, it is characterized in that adopting the two boric acid esters of diazosulfide to react by Suzuki with bromo thiophene-diazosulfide derivative, the novel organic solar cell material of preparation based on thiophene-diazosulfide p-n junction structure, is shown below:
Wherein, R is C
1-C
12alkyl,
This reaction is that in above formula, Suzuki linked reaction occurs for monomer 1 and monomer 2 under tetra-triphenylphosphine palladium Pd (PPh3) 4 katalysis.
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| CN201410077634.7A CN103880834A (en) | 2014-03-05 | 2014-03-05 | Organic solar cell material and preparation method thereof |
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| CN201410077634.7A CN103880834A (en) | 2014-03-05 | 2014-03-05 | Organic solar cell material and preparation method thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106008558A (en) * | 2016-06-02 | 2016-10-12 | 南京邮电大学 | Thiadiazole based polycyclic aromatic hydrocarbon organic semiconductor material, preparation method and application thereof in photoelectric devices |
| CN109545981A (en) * | 2018-11-27 | 2019-03-29 | 江苏拓正茂源新能源有限公司 | A kind of organic solar batteries and preparation method thereof |
| JP2019087662A (en) * | 2017-11-08 | 2019-06-06 | 国立大学法人山口大学 | Alternate accumulation type oligomer and manufacturing method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1671675A (en) * | 2002-06-29 | 2005-09-21 | 科文有机半导体有限公司 | 2,1,3-benzothiadiazoles for use as electronic active components |
| WO2010062015A1 (en) * | 2008-11-25 | 2010-06-03 | 주식회사 동진쎄미켐 | Novel organic dye containing benzothiadiazole chromophore and preparation method thereof |
| CN101993440A (en) * | 2009-08-25 | 2011-03-30 | 中国科学院化学研究所 | Benzothiadiazole-based multi-arm conjugated molecules as well as preparation method and application thereof |
| CN101671428B (en) * | 2008-09-09 | 2011-08-03 | 中国科学院化学研究所 | Conjugated polymer based on condensed ring thiophene and diazosulfide as well as preparation method and application thereof |
-
2014
- 2014-03-05 CN CN201410077634.7A patent/CN103880834A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1671675A (en) * | 2002-06-29 | 2005-09-21 | 科文有机半导体有限公司 | 2,1,3-benzothiadiazoles for use as electronic active components |
| CN101671428B (en) * | 2008-09-09 | 2011-08-03 | 中国科学院化学研究所 | Conjugated polymer based on condensed ring thiophene and diazosulfide as well as preparation method and application thereof |
| WO2010062015A1 (en) * | 2008-11-25 | 2010-06-03 | 주식회사 동진쎄미켐 | Novel organic dye containing benzothiadiazole chromophore and preparation method thereof |
| CN101993440A (en) * | 2009-08-25 | 2011-03-30 | 中国科学院化学研究所 | Benzothiadiazole-based multi-arm conjugated molecules as well as preparation method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| 付钰，等: "非富勒烯小分子有机太阳能电池电子受体材料的研究进展", 《化学学报》, vol. 72, 15 February 2014 (2014-02-15), pages 158 - 170 * |
| 徐巍栋，等: "水溶性共轭聚合物研究与进展", 《中国科学：化学》, vol. 41, no. 3, 31 March 2011 (2011-03-31), pages 409 - 423 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106008558A (en) * | 2016-06-02 | 2016-10-12 | 南京邮电大学 | Thiadiazole based polycyclic aromatic hydrocarbon organic semiconductor material, preparation method and application thereof in photoelectric devices |
| CN106008558B (en) * | 2016-06-02 | 2019-01-08 | 南京邮电大学 | The polycyclic aromatic hydrocarbon organic semiconducting materials of one kind based on thiadiazoles and preparation method thereof and in photoelectric device application |
| JP2019087662A (en) * | 2017-11-08 | 2019-06-06 | 国立大学法人山口大学 | Alternate accumulation type oligomer and manufacturing method thereof |
| CN109545981A (en) * | 2018-11-27 | 2019-03-29 | 江苏拓正茂源新能源有限公司 | A kind of organic solar batteries and preparation method thereof |
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Application publication date: 20140625 |