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Dithiophene ring-fused germanium pentadiene-fluoroquinoxaline conjugated polymer

A conjugated polymer, bisthieno technology, applied in the field of bisthienocyclodermopentadiene-fluoroquinoxaline conjugated polymers, 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. properties, but so far there are no studies and 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

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Example 1: Synthesis of 6-fluoro-5,8-dibromo-2,3-bis(3-octyloxyphenyl)quinoxaline as an electrolytic unit

[0036] (1) Preparation of 4-fluoro-3,6-dibromo-1,2-phenylenediamine (compound 2)

[0037] Follow the reaction equation shown below:

[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, spin off ethanol, add 160ml of water, extract with ethyl acetate, wash the organic phase with saturated brine, and finally anhydrous MgSO 4 dry. The organic solvent was removed by concentration, and the obtained crude product was purified by a silica gel column using n-hexane / ethyl acetate (25:1, v / v) as the eluent to obtain compound 2, m=3.5g, and the yield was 78%.

[0040] (2) Preparation of 1,2-bis(3-octyloxyphenyl)ethanedione (compound 5)

[0041] Follow the reaction equation sh...

Embodiment 2

[0049] Example 2: Synthesis of 6-fluoro-5,8-dibromo-2,3-bis(4-octyloxyphenyl)quinoxaline (compound 8)

[0050] Follow the reaction equation shown below:

[0051]

[0052] Using 4-fluoro-3,6-dibromo-1,2-phenylenediamine and 1,2-bis(4-octyloxyphenyl)ethanedione as raw materials, completely follow the method for the synthesis of compound 6 to obtain the compound 8. The yield is 82%.

Embodiment 3

[0054] Synthesis of the electroporous unit 6,7-difluoro-5,8-dibromo-2,3-bis(3-octyloxyphenyl)quinoxaline (compound 11)

[0055] (1) Preparation of 4,5-difluoro-3,6-dibromo-1,2-phenylenediamine (compound 10)

[0056] Follow the reaction equation shown below:

[0057]

[0058] 5,6-difluoro-4,7-dibromo-2,1,3-benzothiadiazole (10 g, 0.031 mol) was dissolved in 300 ml of 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 obtained crude product was concentrated and purified by silica gel column chromatography, and the eluent was n-hexane / ethyl acetate (20:1, v / v) to obtain 4,5-difluoro-3,6-dibromo-1 , 2-phenylenediamine 6.1g, yield 65%.

[0059] (2) Preparation of 6,7-difluoro-5,8-dibromo-2,3-bis(3-octyloxyphenyl)quinoxaline (compo...

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Abstract

The invention relates to a dithiophene ring-fused germanium pentadiene-fluoroquinoxaline conjugated polymer the structural general formula of which is as shown in a formula I. The polymer is prepared through Stille coupling reaction of 2,6-di(trimethyltin)-4,4-di(2-ethylhexyl)-4-germanium-dithiophene [3,2-b,2',3'-d] ring-fused germanium pentane and a di-bromine substituted fluoroquinoxaline monomer, 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 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 polymers, in particular to a bisthienocyclodermopentadiene-fluoroquinoxaline conjugated polymer. Background technique [0002] Energy is the strategic basis for the social and economic development of all countries in the world in the future. Solar energy is an inexhaustible, pollution-free and clean energy, and one of the most promising energy sources. The direct conversion of solar energy into electricity and heat has long been a research focus of scientists. In 1954, the Bell Research Institute of the United States successfully developed silicon solar cells, creating a precedent for photoelectric conversion research. However, the cost of raw materials for silicon cells is high, the production process is complicated, and the material itself is not conducive to reducing costs, which limits its wider use. One of the effective ways to develop low-cost solar cells is to start with materials and find new so...

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键弥育华安忠维陈冬
Owner XIAN MODERN CHEM RES INST
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