WO2011072435A1 - 含噻吩有机光电材料、其制造方法和太阳能电池器件 - Google Patents
含噻吩有机光电材料、其制造方法和太阳能电池器件 Download PDFInfo
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- WO2011072435A1 WO2011072435A1 PCT/CN2009/075548 CN2009075548W WO2011072435A1 WO 2011072435 A1 WO2011072435 A1 WO 2011072435A1 CN 2009075548 W CN2009075548 W CN 2009075548W WO 2011072435 A1 WO2011072435 A1 WO 2011072435A1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
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- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/105—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing a methine or polymethine dye
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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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/142—Side-chains containing oxygen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/10—Definition of the polymer structure
- C08G2261/14—Side-groups
- C08G2261/143—Side-chains containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
- C08G2261/32—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain
- C08G2261/322—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed
- C08G2261/3223—Monomer units or repeat units incorporating structural elements in the main chain incorporating heteroaromatic structural elements in the main chain non-condensed containing one or more sulfur atoms as the only heteroatom, e.g. thiophene
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/70—Post-treatment
- C08G2261/72—Derivatisation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G2261/90—Applications
- C08G2261/91—Photovoltaic applications
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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
Definitions
- the present invention relates to the field of organic materials, and in particular to a thidium-containing.
- the organic photoelectric material, its manufacturing method, and solar cell device are classified.
- Organic solar cells are a new type of solar cells. Compared with inorganic semiconductor materials, which are limited in source, expensive, toxic, complicated in preparation process and high in cost, they have some advantages that inorganic solar cells cannot match, such as a wide range of materials. Structure diversity and controllability, low cost, safety and environmental protection, simple production process, light weight, large area flexible preparation, etc., can be widely used in various fields such as construction, lighting and power generation, with important development and application. prospect. Therefore, many research institutions and enterprises at home and abroad have given considerable attention and input. However, so far, the photoelectric conversion efficiency of organic solar cells is still much lower than that of inorganic solar cells. Therefore, the development of new organic optoelectronic materials is important for improving the efficiency of organic solar cells and other semiconductor devices. To be meaningful. Summary of the invention
- the present invention provides a thiophene having a broad response to light and good stability. It is divided into organic photoelectric materials, and a simple synthetic route with low cost and thiophene. A method of manufacturing an organic photoelectric material.
- the present invention also provides a thiene containing the above.
- a solar cell device that is divided into organic photoelectric materials.
- An organic photoelectric material comprising a compound represented by the following structural formula (1):
- R 2 , R 3 and R 4 are the same or different straight chain, branched or cyclic alkyl chain represented by hydrogen or 1 to 12 carbon atoms, and m, n, p are the same or different 0 An integer between 6 and 6.
- a method for producing a thiophene organic photoelectric material comprising the steps of:
- R 2 , R 3 are the same or different linear, branched or cyclic alkyl chain represented by hydrogen or 1 to 12 carbon atoms, and m, n, p are the same or different 0 to 6 An integer between
- the compounds A and B are respectively subjected to condensation reaction with malononitrile or the compounds A and B are subjected to Stille coupling reaction with the compound C under the conditions of a catalyst/solvent;
- the product of the condensation reaction is subjected to a Stille coupling reaction with the compound C or the product of the Stille coupling reaction is subjected to a condensation reaction with malononitrile under the conditions of a catalyst/solvent to obtain a compound represented by the following structural formula (1):
- a solar cell device comprising a glass substrate, a transparent anode, an intermediate auxiliary layer, an active layer and a cathode which are sequentially laminated, the active layer comprising an electron donor material and an electron acceptor material, wherein the electron donor material is The above thiophene-containing organic photoelectric material.
- Figure 1 is a thiol-containing embodiment of the present invention.
- Fig. 2 is a thiol group according to an embodiment of the present invention.
- FIG. 3 is a thiol-containing embodiment of the invention. The structure of a solar cell device divided into organic photoelectric materials is shown. detailed description
- FIG. 1 there is shown a structural formula (1) of a compound containing a thiophene organic photoelectric material according to an embodiment of the present invention, that is, a compound represented by the following structural formula (1):
- R 2 , R 3 and R 4 are the same or different straight chain, branched or cyclic alkyl chain represented by hydrogen or 1 to 12 carbon atoms, and m, n, p are the same or different 0 An integer between 6 and 6.
- the thiophene is included.
- the organic photoelectric material is a double thiophene structure, and its molecular weight is small, and the quality of the produced product is light.
- the same groups are, for example, straight-chain alkyl groups having 6 carbon atoms, i.e., hexane groups, and R 3 and R 4 are each preferably hydrogen.
- m, n, p are each preferably 1, ie the thiol.
- the organic photoelectric material is a polythiophene.
- the method for manufacturing an organic photoelectric material includes the following steps:
- R 2 , R 3 , and R 4 are the same or different straight chain, branched or cyclic alkyl chain represented by hydrogen or 1 to 12 carbon atoms, and m, n, p are the same or different 0 An integer between 6;
- step S10 the compounds A, B, C and malononitrile are commercially available or can be prepared by existing synthetic methods and will not be described in detail herein.
- the above-mentioned thiophene The description of the sub-organic optoelectronic material is substantially the same, and in one embodiment of the invention, the thiophene is included.
- the organic photoelectric material is a double thiophene structure, the molecular weight thereof is small, the quality of the produced product is light, and the corresponding raw material sources are relatively wide.
- R 2 is the same group, for example, all of a linear alkyl group having 6 carbon atoms, i.e., a hexane group, and both R 3 and R 4 are preferably hydrogen.
- m, n, p are each preferably 1.
- steps S20 and S30 the order of the condensation reaction and the Stille coupling reaction are different, and can be divided into two alternatives.
- the first scheme is: under the conditions of a catalyst/solvent, the compounds A and B are respectively subjected to a condensation reaction with malononitrile, and the acid groups in the compounds A and B are respectively substituted by an ethylenediylvinyl group. Then, under the catalyst/solvent condition, the product formed by the condensation reaction is subjected to Stille coupling reaction with the compound C to obtain the thiophene-containing organic photoelectric material.
- the second scheme is: condensation reaction, compound A and B are first subjected to Stille coupling reaction with compound C to form a polythiophene having a dialdehyde group, and then the polythiophene is subjected to a condensation reaction with malononitrile to cause the polythiophene on the polythiophene.
- the dialdehyde groups are each substituted with an ethylenedicyanovinyl group to obtain the thiophene-containing organic photoelectric material.
- the molar ratio of each reactant may be 1:1 or other reaction ratio, and the following reaction of the present embodiment can be carried out without affecting the progress of the reaction. The following is introduced separately.
- the first option includes the following steps:
- Step i performing a condensation reaction, and subjecting the compounds A and B to a malononitrile reaction under a catalyst/solvent condition, respectively, the aldehyde groups in the compounds A and B are respectively substituted by an ethylenedicyanovinyl group, respectively.
- Compounds A' and B', the reaction process is as follows:
- the catalyst of the step i is pyridine or triethylamine, preferably pyridine;
- the solvent is ethanol, decyl alcohol, dichlorodecane, trichlorodecane, tetrahydrofuran, ethyl acetate, DMF, toluene or acetone, preferably Ethanol.
- purification is carried out, specifically: after the reaction product is washed several times with a saturated aqueous solution of sodium chloride, extraction and drying are carried out, and after the extraction, the filtrate is collected and subjected to rotary evaporation, and then subjected to silica gel column chromatography. A purified product is obtained.
- the extractant may be ethyl acetate
- the desiccant may be anhydrous magnesium sulfate
- the silica gel column chromatography may be carried out under petroleum ether: ethyl acetate as the eluent.
- Step ii The compound A' and B' formed in the step i are subjected to a Stille coupling reaction with the compound C under a catalyst/solvent condition to obtain a thiophene-containing organic photoelectric material, and the reaction process is as follows:
- the catalyst of step ii may be an organic palladium catalyst such as Pd 2 (dba) 3 /P(o-Tol) 3 , Pd(PPh 3 ) 4 or Pd(PPh 3 ) 2 Cl 2 , preferably Pd 2 ( Dba) 3 /P(o-Tol) 3 .
- the solvent may be tetrahydrofuran, dichlorodecane, ethylene glycol dioxime ether, benzene or toluene, preferably tetrahydrofuran.
- the purification is further carried out, specifically: returning the reaction product to room temperature, adding a KF solution, stirring for several minutes, adding a saturated aqueous solution of sodium chloride, extracting and drying, and collecting the filtrate and steaming it.
- the obtained crude product was filtered and separated by silica gel column chromatography to give purified product.
- the extracting agent may be ethyl acetate
- the desiccant may be anhydrous magnesium sulfate
- the silica gel column chromatography may be carried out under petroleum ether: dichlorosilane as the eluent.
- the second option includes the following steps:
- Step i Stille-coupling the compounds A and B with the compound C to form a polythiophene having a dialdehyde group, and the reaction process is as follows:
- reaction conditions of the steps of the second embodiment are substantially the same as those of the step ii of the first embodiment, and the yield of the step is also substantially the same as that of the step ii, and details are not described herein again.
- Step ii performing a condensation reaction of the polythiophene having a diacid group formed with the step with malononitrile, and replacing the dialdehyde group on the polythiophene with an ethylenedicyanovinyl group, respectively, to obtain the above-mentioned thiophene-containing organic photoelectric material.
- the reaction process is as follows:
- reaction conditions of the steps of the second embodiment are substantially the same as those of the step i of the first embodiment, and are not described herein again.
- the above contains thiophene.
- the organic optoelectronic material comprises a plurality of thiophene rings, has a moderate energy band gap, a wide spectral response, a wavelength band of about 250-650 nm, substantially covers the visible light band, and also has good thermal stability and environmental stability, performance Better photoelectric performance. Therefore, the thiophene is contained.
- Organic optoelectronic materials are a wide range of materials that can be used, for example, in organic solar cells, organic field effect transistors, organic electroluminescence, organic optical storage, organic nonlinear materials, and organic lasers.
- a solar cell device comprising an organic photoelectric material, comprising a glass substrate 11, a transparent anode 12, an intermediate auxiliary layer 13, an active layer 14, and a cathode 15 which are sequentially laminated, and the intermediate auxiliary layer 13 is made of polyethylene dioxythiophene: polystyrene- A sulfonic acid composite material (abbreviated as PEDOT:PSS), the active layer 14 includes an electron donor material and an electron acceptor material, and the electron donor material uses the above-mentioned thiophene.
- PEDOT polystyrene- A sulfonic acid composite material
- the electron acceptor material may be [6,6]phenyl-C 61 -butyric acid acrylate (abbreviated as PCBM).
- the transparent anode 12 may be indium tin oxide (abbreviated as ITO), preferably a square
- ITO indium tin oxide
- the resistance is 10-20 ⁇ /indium tin oxide.
- the cathode 15 can be an aluminum electrode.
- the glass base layer 11 can be used as a bottom layer. When fabricated, the germanium electrode is first deposited on the glass base layer 11, the intermediate auxiliary layer 13 is formed on the germanium electrode, and the thiophene is contained.
- the organic photoelectric material and the electron acceptor material are deposited on the intermediate auxiliary layer 13 by a vacuum evaporation technique to form the active layer 14, and then the cathode 15 is deposited on the active layer 14 by a vacuum evaporation technique to obtain the above solar cell device.
- the organic optoelectronic material absorbs light energy and generates excitons, which then migrate to the interface of the electron donor/acceptor material, and transfer the electrons to an electron acceptor material, such as PCBM, to separate the charge, thereby forming Free carriers, ie free electrons and holes.
- an electron acceptor material such as PCBM
- organic optoelectronic materials can more fully utilize light energy to achieve higher photoelectric conversion efficiency and increase the power generation capability of solar cell devices.
- the organic material can also reduce the quality of the solar cell device, and can be fabricated by techniques such as vacuum evaporation, which is convenient for mass production.
- the thiol-containing is exemplified below by way of specific examples.
- the thiophene contained in the first embodiment is known.
- the organic photoelectric material has a symmetrical structure, has a pentathiophene ring and two pairs of an aryl group, and the aryl group serves as an electron withdrawing group, and the thiophene is formed by such a uniform symmetrical structure.
- the organic photoelectric materials have better light absorption properties and photoelectric properties than other polythiophene rings.
- the preparation method of the bisthiophene adopts the first The specific operation of a scheme is as follows:
- the organic photoelectric material has a symmetrical structure. Therefore, the structures of the compounds A and B in this step are the same, and the products produced are also the same, that is, the structures of the compounds A' and B' are the same, so that only one step 1) is required. , simplifying the preparation process and reducing costs if thiophene is contained.
- the organic photoelectric material is not a symmetrical structure, and if the structures of the compounds A and B are different, it is necessary to carry out the steps 1) for different raw materials.
- the specific preparation steps are as follows: ethanol (50.0 mL) and 5-bromo-5,-hexyl-2,2,-dithiophene are sequentially added.
- the specific preparation steps are as follows: 50 mL of THF is added to the pressure tube, and 2-((2-bromo-5-(5-hexylthiophen-2-yl)thiophen-3-yl)indenyl)propane Nitrile (0.61 g, 1.50 mmol, belonging to compound A' or ⁇ ') and 2,5-bis(tributyltin)-thiophene (0.46 g, 0.70 mmol, belonging to compound C), nitrogen 10 minutes below the liquid level, then Pd 2 (dba) 3 (0.013 g, 0.014 mol) and P (o-Tol) 3 ( 0.0083 g, 0.027 mmol) were added, and nitrogen gas was passed to the surface for 10 minutes.
- 2-((2-bromo-5-(5-hexylthiophen-2-yl)thiophen-3-yl)indenyl)propane Nitrile (0.61 g, 1.50 mmol, belonging to compound A' or
- the preparation method of the bisthiophene is specifically operated as follows according to the second scheme.
- the organic photoelectric material has a symmetrical structure, and therefore, the compounds A and B have the same structure in this step, and it is only necessary to provide a raw material to directly carry out the step 1), thereby simplifying the preparation process and reducing the cost.
- Step 1) The specific preparation steps are as follows: 15 mL of THF is added to the pressure tube, and 5-bromo-5,-hexyl-2,2,-dithiophene-4-furaldehyde (0.36 g, 1.00 mmol) is quickly added. And 2,5-bis(tributyltin)-thiophene (0.33 g, 0.50 mmol), nitrogen gas was passed to the surface for 10 minutes, then Pd 2 (dba) 3 ( 0.0092 g, 0.010 mol ) and P (o-Tol) were added. 3 (0.0061 g, 0.020 mmol), nitrogen gas was passed to the surface for 10 minutes, capped, warmed to 80 ° C, and allowed to react overnight.
- the specific preparation steps are as follows: sequentially adding ethanol (40.0 mL), 5, 5""-dihexyl-4', 3"'-diacid-2, 2':5', 2":5", 2"' :5"', 2""-bihexathiophene (0.20 g, 0.32 mmol) and malononitrile (0.046 g, 0.70 mmol), heated to reflux. 3 drops of pyridine were added quickly and allowed to react overnight. Washed with saturated aqueous sodium chloride After several times, it was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. After evaporation, the filtrate was collected and then evaporated.
- the above-mentioned thiophene is contained.
- the fraction is a five-membered ring structure that conforms to the shock rule, has a moderate energy band gap, a wide optical response, good thermal stability and environmental stability.
- the above thiophene-containing organic photoelectric material has two pairs of cyano groups, and the cyano group is an electron-withdrawing group, the optical response range of the material can be further widened, and the photoelectric properties of the material can be improved.
- it contains thiophene.
- a relatively simple synthetic route is employed, thereby reducing manufacturing costs.
- the solar cell device adopts a thiophene-containing. By dividing the organic photoelectric material, not only can the photoelectric conversion efficiency be improved, but also the quality of the solar cell device can be alleviated, and the preparation in large quantities can be facilitated.
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Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
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EP09852173.5A EP2514797B1 (en) | 2009-12-14 | 2009-12-14 | Thiophene-containing organic photoelectric materials, their perparation methods and solar cell devices |
PCT/CN2009/075548 WO2011072435A1 (zh) | 2009-12-14 | 2009-12-14 | 含噻吩有机光电材料、其制造方法和太阳能电池器件 |
US13/514,947 US8703971B2 (en) | 2009-12-14 | 2009-12-14 | Thiophene-containing organic photoelectric materials, their preparation methods and solar cell devices |
CN2009801615284A CN102575154A (zh) | 2009-12-14 | 2009-12-14 | 含噻吩有机光电材料、其制造方法和太阳能电池器件 |
JP2012542334A JP5599469B2 (ja) | 2009-12-14 | 2009-12-14 | チオフェン含有有機光電材料、並びにその製造方法及び太陽電池部品 |
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PCT/CN2009/075548 WO2011072435A1 (zh) | 2009-12-14 | 2009-12-14 | 含噻吩有机光电材料、其制造方法和太阳能电池器件 |
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JP2013119589A (ja) * | 2011-12-07 | 2013-06-17 | Sumitomo Chemical Co Ltd | 高分子化合物及び電子素子 |
CN103788682B (zh) * | 2014-02-21 | 2015-08-12 | 太原理工大学 | 固/液状态下荧光颜色不同的有机荧光染料及其制备方法 |
KR102159301B1 (ko) | 2018-10-05 | 2020-09-23 | 부경대학교 산학협력단 | 유기태양전지 도너용 공액 저분자 화합물 및 이를 포함하는 유기태양전지 |
SE543571C2 (en) * | 2019-02-07 | 2021-03-30 | Christian Strietzel | Conducting redox oligomers |
KR102385131B1 (ko) | 2020-09-17 | 2022-04-11 | 부경대학교 산학협력단 | 시안기를 포함하는 고분자 태양전지 도너용 퀴녹살린계 공액 고분자 및 이를 포함하는 고분자 태양전지 |
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CN101208349A (zh) * | 2005-05-19 | 2008-06-25 | 日产化学工业株式会社 | 具有磷酸酯的噻吩化合物及其制造方法 |
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CN101282959A (zh) * | 2005-08-18 | 2008-10-08 | 日产化学工业株式会社 | 具有磺酰基的噻吩化合物及其制备方法 |
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