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Dithiophene ring-fused germanium pentadiene-fluoroquinoxaline conjugated polymer

A conjugated polymer, double thieno technology, applied in the field of functional polymer materials, to achieve the effect of increasing the open circuit voltage

Inactive Publication Date: 2012-12-12
XIAN MODERN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In view of the above-mentioned influence of fluorine atoms on material properties, the introduction of fluorine atoms into the electron-deficient unit of quinoxaline to prepare a new type of fluorine-containing donor-acceptor polymer is expected to further reduce HOMO and increase the open circuit voltage, thereby improving the photovoltaic performance of the device. performance, but so far there are no reports on the preparation of such materials and their application in polymer photovoltaic cells

Method used

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  • Dithiophene ring-fused germanium pentadiene-fluoroquinoxaline conjugated polymer
  • Dithiophene ring-fused germanium pentadiene-fluoroquinoxaline conjugated polymer
  • Dithiophene ring-fused germanium pentadiene-fluoroquinoxaline conjugated polymer

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Experimental program
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Effect test

Embodiment 1

[0036] Preparation of 6-fluoro-5,8-bis(5-bromo-4-hexylthiophene)-2,3-bis(3-octyloxyphenyl)quinoxaline:

[0037] (1) The preparation of 4-fluoro-3,6-dibromo-1,2-phenylenediamine (compound 1) is carried out according to the following reaction equation:

[0038]

[0039] 5-Fluoro-4,7-dibromo-2,1,3-benzothiadiazole (5 g, 0.016 mol) was dissolved in 150 ml of absolute ethanol, and NaBH was added in batches at 0 °C 4 (11.1g, 0.29mol), and then reacted at room temperature for 20h. After the reaction, concentrate to remove ethanol, add 160ml of water, extract with ethyl acetate, wash the organic phase with brine, and finally anhydrous MgSO 4 dry. The crude product obtained after concentration to remove the organic solvent was purified by a silica gel column, and the eluent was n-hexane / ethyl acetate (25:1, v / v) to obtain 4-fluoro-3,6-dibromo-1,2- 3.5 g of phenylenediamine, yield 78%.

[0040] (2) Preparation of 1,2-bis(3-octyloxyphenyl)ethanedione (compound 2)

[0041] Follow ...

Embodiment 2

[0056] Synthesis of 6-fluoro-5,8-bis(5-bromo-4-hexylthiophene)-2,3-bis(4-octyloxyphenyl)quinoxaline (compound 9):

[0057] Follow the reaction equation shown below:

[0058]

[0059] The synthesis method is the same as that of compound 5, except that 1,2-bis(3-octyloxyphenyl)ethanedione is replaced by 1,2-bis(4-octyloxyphenyl)ethanedione.

Embodiment 3

[0061] Synthesis of 6,7-difluoro-5,8-bis(5-bromo-4-hexylthiophene)-2,3-bis(3-octyloxyphenyl)quinoxaline (compound 14):

[0062] (1) Preparation of 4,5-difluoro-3,6-dibromo-1,2-phenylenediamine (compound 11)

[0063] Follow the reaction equation shown below:

[0064]

[0065] Compound 10 (10g, 0.031mol) was dissolved in 300ml absolute ethanol, and NaBH was added in batches at 0°C 4 (22.2g, 0.59mol), then reacted at room temperature for 5h. After the reaction, concentrate to remove ethanol, add 200ml of water, extract with ethyl acetate, wash the organic phase with saturated brine, and finally anhydrous MgSO 4 dry. The crude product obtained by concentration was purified by silica gel column, and the eluent was n-hexane / ethyl acetate (20:1, v / v) to obtain 4,5-difluoro-3,6-dibromo-1,2-benzene Diamine 6.1g, yield 65%.

[0066] (2) Preparation of 6,7-difluoro-2,3-bis(3-octyloxyphenyl)quinoxaline (compound 12)

[0067] Follow the reaction equation shown below:

[0068] ...

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Abstract

The invention relates to a dithiophene ring-fused germanium pentadiene-fluoroquinoxaline conjugated polymer the structural formula of which is as shown in a formula I. The polymer is prepared through Stille coupling reaction of a 2,6-di(isooctyl)-4,4-di(2-ethylhexyl)-4-germanium-dithiophene [3,2-b,2',3'-d] ring-fused germanium pentylene monomer and a fluoro-5, 8-di(5-bromine thienyl) quinoxaline monomer which serves as an electron acceptor unit, and is used as a donor material of a bulk heterojunction solar cell. As for the polymer, a strong electron withdraw group fluorine atom is introduced to an electron-shortage unit quinoxaline to effectively reduce the HOMO energy level of the material, so that the open-circuit voltage of a polymer photovoltaic cell is improved.

Description

technical field [0001] The invention belongs to the field of functional polymer materials, in particular to a bisthienocyclodermopentadiene-fluoroquinoxaline conjugated polymer. Background technique [0002] Energy issues have attracted much attention. Solar energy is an inexhaustible, non-polluting and clean energy, and one of the most promising energy sources in the future. It has always been the goal of scientists to directly convert solar energy into electricity and heat for the benefit of mankind. Currently, the most widely researched and used solar cells are mainly monocrystalline silicon, polycrystalline silicon and amorphous silicon series cells. However, the cost of raw materials for silicon cells is high and the production process complex, limiting its wider use. One of the effective ways to develop low-cost solar cells is to start with materials and find new solar cell materials that are cheap, high in environmental stability, and have good photovoltaic effects. ...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/46
CPCY02E10/549
Inventor 高潮王维平武海梅陈冬弥育华安忠维田地
Owner XIAN MODERN CHEM RES INST
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