Bithiophene silicon pentalene-fluoroquinoxaline conjugated polymer

A technology of cyclosilyl pentadiene and conjugated polymer, which is 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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  • Bithiophene silicon pentalene-fluoroquinoxaline conjugated polymer
  • Bithiophene silicon pentalene-fluoroquinoxaline conjugated polymer
  • Bithiophene silicon pentalene-fluoroquinoxaline conjugated polymer

Examples

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

[0038] Follow the reaction equation shown below:

[0039]

[0040] 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%.

[0041] (2) Preparation of 1,2-bis(3-octyloxyphenyl)ethanedione (compound 2):

[0042] Follow the reaction...

Embodiment 2

[0056] Synthesis of 6-fluoro-5,8-bis(5-bromo-4hexylthiophene)-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] 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), and 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-5,8-dibromo-2,3-bis(3-octyloxyphenyl)quinoxaline (compound 12):

[00...

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Abstract

The invention relates to a bithiophene silicon pentalene-fluoroquinoxaline conjugated polymer which has a structural formula shown as a formula I. The polymer is prepared by subjecting 2,6-bi(trimethyltin)-4, 4-bi(2-ethylhexyl)-4-hydrogen-bithiophene[3,2-b,2',3'-d] pentane monomer serving as an electron supply unit and bibromide substituted fluoro-5,8-bithiophene quinoxaline monomer serving as an electron receiving unit to Stille coupling reaction and used for donor materials of polymer bulk heterojunction solar cells. Strong electron drawing group fluorine atoms are introduced on an electron deficiency quinoxaline, so that HOMO energy level of materials can be effectively lowered to increase open-circuit voltage of polymer photovoltaic cells.

Description

technical field [0001] The invention belongs to the field of functional polymer materials, in particular to a bisthienocyclosilicene-fluoroquinoxaline conjugated polymer. Background technique [0002] After the oil crisis in the 1970s, the United States, Japan, Germany and other developed countries put solar energy at the top of the key development targets of new renewable energy in the future, and the utilization of solar energy has been greatly developed. Among them, the research and development of solar cells that directly convert solar energy into electrical energy is one of the fastest growing and most dynamic research fields in recent years. 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. Polymer solar cells have obvious advantages such as low cost, good flexibility, and easy preparation. Therefore, this type of s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
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陈键
Owner XIAN MODERN CHEM RES INST
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