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Bithiophene silicon pentalene-fluoroquinoxaline conjugated polymer

A technology of cyclosilipentadiene and conjugated polymers, which is applied in the field of functional polymers, can solve problems such as reducing HOMO energy, and achieve the effect of increasing 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 the properties of materials, introducing fluorine atoms into quinoxaline, a power-deficient unit, to prepare a new type of fluorine-containing donor-acceptor polymer is expected to reduce the HOMO energy, increase the open circuit voltage, and further improve the device performance. Photovoltaic properties, but the preparation of such materials and their application in polymer photovoltaic cells have not been studied and reported so far

Method used

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  • Bithiophene silicon pentalene-fluoroquinoxaline conjugated polymer

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Synthesis of the electroporous unit 6-fluoro-5,8-dibromo-2,3-bis(3-octyloxyphenyl)quinoxaline:

[0035] (1) Preparation of 4-fluoro-3,6-dibromo-1,2-phenylenediamine (compound 2)

[0036] Follow the reaction equation shown below:

[0037]

[0038] 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 saturated 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%.

[0039] (2) Preparation of 1,2-bis(3-octyloxyphenyl)ethanedione (compound 5)

[0040] Follow the ...

Embodiment 2

[0048] Example 2: Synthesis of 6-fluoro-5,8-dibromo-2,3-bis(4-octyloxyphenyl)quinoxaline (compound 8)

[0049] Follow the reaction equation shown below:

[0050]

[0051] Using 4-fluoro-3,6-dibromo-1,2-phenylenediamine and 1,2-bis(4-octyloxyphenyl)ethanedione as raw materials, completely follow the method of compound 6 to obtain the target Product, yield 82%.

Embodiment 3

[0053] Synthesis of 6,7-difluoro-5,8-dibromo-2,3-bis(3-octyloxyphenyl)quinoxaline as an electroporous unit

[0054] (1) Preparation of 4,5-difluoro-3,6-dibromo-1,2-phenylenediamine (compound 10)

[0055] Follow the reaction equation shown below:

[0056]

[0057] 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 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%.

[0058] (2) Preparation of 6,7-difluoro-5,8-dibromo-2,3-bis(3-octyloxyphenyl)quinoxaline (compound 11)

[0059] Follow the r...

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Abstract

The invention relates to a bithiophene silicon pentalene-fluoroquinoxaline conjugated polymer which has a general structural formula shown as a formula I. The polymer is prepared by subjecting bithiophene silicon pentalene monomer serving as an electron supply unit and bibromide substituted fluoroquinoxaline monomer serving as an electron receiving unit to Stille coupling reaction and 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 polymers, in particular to a bisthienocyclosilicene-fluoroquinoxaline conjugated polymer. Background technique [0002] Solar energy is one of the most promising energy sources in the future, and it is an inexhaustible pollution-free and clean energy source. Since the first silicon solar cell was successfully developed in 1954, various forms of solar cells have come out one after another. At present, the most widely researched and used solar cells are mainly monocrystalline silicon, polycrystalline silicon and amorphous silicon series cells. However, the raw materials of silicon cells The high cost and complex production process limit its wider use. Polymer solar cells have obvious advantages such as low cost, good flexibility, and easy preparation, and the performance of solar cells can be effectively improved by modifying materials. Therefore, this type of solar cell has important development and app...

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 高潮王维平武海梅刘红利弥育华安忠维刘建群
Owner XIAN MODERN CHEM RES INST
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