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Block copolymer and photoelectric conversion element

A technology of block copolymers and polymers, which can be used in electrical components, electrical solid devices, circuits, etc., and can solve problems such as weak light absorption

Inactive Publication Date: 2013-12-11
KURARAY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, narrow bandgap polymers have weak light absorption in the visible region, and thus the very expensive C 70 Fullerene derivatives are used as electron-accepting materials, which is undesirable

Method used

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  • Block copolymer and photoelectric conversion element
  • Block copolymer and photoelectric conversion element
  • Block copolymer and photoelectric conversion element

Examples

Experimental program
Comparison scheme
Effect test

Embodiment approach

[0174] Examples of the present invention are described in detail, but the scope of the present invention is not limited by these Examples.

[0175] The measurement and purification methods of the physical properties of the materials produced in the above respective steps and in the following steps were performed as follows.

[0176] [Weight average molecular weight (Mw), number average molecular weight (Mn)]

[0177] Based on condensate obtained in polystyrene equivalent values ​​from a GPC apparatus (HLC-8020, trade name, manufactured by Tosoh Corporation) having two columns connected in series (trade name, TSKgel Multipore HZ, manufactured by Tosoh Corporation) Gel Permeation Chromatography (GPC) measurements determine the number average molecular weight and weight average molecular weight. The measurement was performed at 40° C. using chloroform as a solvent.

[0178] [Purification of polymers]

[0179] Purification of the obtained polymer was carried out using a prepara...

Synthetic example 1

[0185] A monomer represented by the following formula (i) was synthesized.

[0186]

[0187] Under a nitrogen atmosphere, cyclopentadieno[2,1-b:3,4-b']dithiophene (0.36 g, 2.0 mmol) and tetrahydrofuran (30 mL) were added to a 100 mL three-necked flask and cooled to below 0°C. Then a 1.6M solution of n-butyllithium in hexane (1.38 mL, 2.2 mmol) was slowly added dropwise, and stirred for 1 hour after the temperature rose to room temperature. After cooling the temperature to 0°C again, 8-bromo-1-iodo-octane (0.64 g, 2.0 mmol) was added, followed by stirring for 1 hour. A 1.6 M solution of n-butyllithium in hexane (1.38 ml, 2.2 mmol) was then slowly added dropwise. After raising the temperature to room temperature, stirring was continued for 1 hour. Cool the temperature below 0°C. Then 8-bromo-1-iodo-octane (0.64 g, 2.0 mmol) was added, followed by stirring for 1 hour. After completing the reaction, the reaction mixture was poured into saturated brine (100 mL) and extracte...

Synthetic example 2

[0190] A monomer represented by the following formula (ii) was synthesized.

[0191]

[0192] Under a nitrogen atmosphere, the compound represented by formula (i) (0.62 g, 1.1 mmol) and tetrahydrofuran (13 mL) were charged into a 100 mL three-necked flask, and then cooled to below 0°C. Subsequently, N-bromosuccinimide (0.39 g, 2.2 mmol) was added slowly, followed by stirring at below 0°C for 1 hour. Raise the temperature to room temperature. After completing the reaction, the reaction mixture was poured into saturated brine (100 mL), followed by extraction with hexane (30 mL×3), followed by washing with water (30 mL×3). The obtained organic layer was dried over sodium sulfate, and then the solvent was evaporated under reduced pressure to obtain a crude product, which was purified by silica gel column chromatography (hexane) to obtain 2, as a yellow solid represented by formula (ii). 6-Dibromo-4,4-bis(8-bromooctyl)cyclopentadieno[2,1-b:3,4-b']dithiophene (0.7 g, 88%).

[...

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Abstract

Provided are: a conjugated block copolymer capable of increasing the amount of optical absorption by a photoelectric conversion active layer and controlling the morphology thereof and capable of achieving excellent photoelectric conversion efficiency; and a photoelectric conversion element comprising a composition including an electron-accepting material using this kind of conjugated block polymer. A pi-electron conjugated block copolymer comprises: a polymer block (A) comprising a monomer unit having at least one heteroaryl skeletal structure selected from a group comprising a fused-ring pi-conjugated structure including at least one thiophene ring in one part of the chemical structure thereof, a fluorene, a carbazole, a dibenzosilole, and a dibenzogermole; and a polymer block (B) having as the monomer unit thereof a thiophene-2, 5-diyl group having a substituent group at least at the 3-position.

Description

technical field [0001] The present invention relates to a novel π-electron conjugated block copolymer, and a photoelectric conversion element made of the copolymer. Background technique [0002] Organic thin-film solar cells produced by coating with solvent-soluble polymer materials have attracted much attention because when compared with inorganic solar cells (which are already made of polycrystalline silicon, amorphous silicon, compound semiconductors, etc. When compared to mainstream solar cells), they can be produced at low cost. [0003] An organic thin film solar cell generally has a photoelectric conversion active layer with a bulk heterojunction structure formed of a mixture of a conjugated polymer and an electron-accepting material. As a specific example, there is an organic thin-film solar cell having a photoelectric conversion active layer comprising poly(3-hexylthiophene) which is a conjugated polymer and [6,6 ]-phenyl C 61 Butyrate methyl ester (PCBM) or a mi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C08K3/04C08L65/00H01L51/42H10K99/00
CPCC08G61/124C08G61/126C08G2261/126C08G2261/3223C08G2261/3241C08G2261/3243C08G2261/3246C08G2261/344C08G2261/91C08K3/045H10K85/113H10K85/151H10K30/50C08K3/04C08L65/00H10K30/30
Inventor 伊泽隆文涉谷宽政杉冈尚稻垣拓也森原靖中原淳裕籐田明士大木弘之
Owner KURARAY CO LTD
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