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Two-dimensional conjugated polymer electron donor material containing disulfhydryl substituted side chain

A conjugated polymer and electron technology is applied in the field of two-dimensional benzodithiophene conjugated polymer electron donor materials and their preparation, and achieves the effects of good electrochemical properties and wide spectral absorption range.

Inactive Publication Date: 2018-06-12
NANJING UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This kind of narrow-bandgap D-A type polymer is based on the two-dimensional conjugated polymer obtained by the copolymerization of dithiol-substituted benzodithiophene and difluoro-substituted benzothiadiazole as the electron acceptor unit as the electron donor. So far, there are no relevant literatures and patents at home and abroad to report its application in polymer donor materials for solar cells.

Method used

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  • Two-dimensional conjugated polymer electron donor material containing disulfhydryl substituted side chain
  • Two-dimensional conjugated polymer electron donor material containing disulfhydryl substituted side chain
  • Two-dimensional conjugated polymer electron donor material containing disulfhydryl substituted side chain

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preparation example Construction

[0033] The preparation method of the D-A type conjugated polymer electron donor material in the polymer solar cell blending active layer of the present invention comprises the following steps:

[0034] a. Add 3-carboxythiophene and dehydrated dichloromethane into an anhydrous two-necked flask, add oxalyl chloride dropwise at 0° C., and stir overnight. The solvent and excess oxalyl chloride were removed by a rotary evaporator, and 1 was obtained as a colorless solid after drying.

[0035] b. Dissolve compound 1 in dehydrated dichloromethane under the protection of nitrogen, add dropwise a solution of diethylamine dissolved in dichloromethane at 0° C., and stir overnight. After the reaction was completed, it was poured into deionized water for extraction, and the organic phases were combined and washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. After removing the solvent, the crude product was separated by column chromatography to obtain yellow li...

Embodiment 1

[0046] (1) 3-Butylthiothiophene

[0047]

[0048] The raw material 3-bromothiophene (6.0g, 36.80mmol), butanethiol (4.35ml, 40.48mmol) was added to anhydrous toluene, and 1,1'-bis(diphenylphosphino)ferrocene ( 816.1mg, 1.47mmol), N,N-diisopropylethylamine (5.23g, 40.48mmol) and Pd 2 (dba) 3 (337.0 mg, 0.37 mmol), then heated to 110 ° C for 12 hours; stopped the reaction, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, spin-dried the organic solvent, and separated by column chromatography to obtain a yellow liquid with a yield of 95 %. Among them, 3-bromothiophene and butanethiol, 1,1’-bis(diphenylphosphino)ferrocene, N,N-diisopropylethylamine, Pd 2 (dba) 3 The molar ratio is 1:1.1:0.04:1.1:0.02.

[0049] (2) 2-Bromo-3-butylthiothiophene

[0050]

[0051] 3-Butylthiothiophene (5.8g, 33.66mmol) was dissolved in dimethylformamide, and after cooling down to 0°C, N-bromosuccinimide (6.0g, 33.66 mmol), reacted at 0°C for 4h, extracted with ethyl ac...

Embodiment 2

[0067] (1) 3-Hexylthiothiophene

[0068]

[0069] Raw materials 3-bromothiophene (6.0g, 36.80mmol), hexane mercaptan (4.79g, 40.48mmol) were added to anhydrous toluene, and N,N-diisopropylethylamine (5.23g, 40.48mmol ), 1,1'-bis(diphenylphosphino)ferrocene (816.1mg, 1.47mmol) and Pd 2 (dba) 3 (337.0mg, 0.37mmol), heated to 110°C for 12 hours; stopped the reaction, extracted with ethyl acetate, and separated by column chromatography to obtain a yellow liquid with a yield of 93%. Among them, 3-bromothiophene and butanethiol, N,N-diisopropylethylamine, 1,1’-bis(diphenylphosphino)ferrocene, Pd 2 (dba) 3 The molar ratio is 1:1.1:1.1:0.04:0.02.

[0070] (2) 2-bromo-3-hexylthiothiophene

[0071]

[0072] Dissolve 3-hexylthiothiophene (5.3g, 26.45mmol) in dimethylformamide, lower the temperature to 0°C under nitrogen protection and stir for 30 minutes, then add N-bromosuccinimide (4.71 g, 26.45mmol), reacted at 0°C for 4h, extracted the product with ethyl acetate after the r...

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Abstract

The invention discloses a two-dimensional conjugated polymer electron donor material containing a disulfhydryl substituted side chain. According to the invention, the photoelectric properties and photovoltaic properties based on the same of the two-dimensional conjugated polymer electron donor material are adjusted through change of a side chain substituted alkylsulphanyl length. The method provided by the invention has mild, simple and easy synthetic steps, cheap synthetic raw materials and low overall preparation cost; the conjugated polymer prepared by using the method provided by the invention has good thermal stability (a decomposition temperature reaches 340 DEG C); an ultraviolet-visible light absorption spectrum shows that the polymer has moderate optical band gap (1.6 to 1.7 eV);compared with a one-dimensional benzo[1,2-b: 4,5-b']dithiophene polymer material, the polymer has wider spectrum absorption range (300 to 900 nm); compared with a monosulfhydryl substituted polymer material, the polymer has lower HOMO energy level; meanwhile, the polymer has good electrochemical properties and large rigid conjugated structure, reinforces intramolecular charge transfer strength, increases intermolecular pi-pi accumulation and polarization effects in a polymer solid phase, and is a potential polymer solar cell blended active-layer electron donor material.

Description

technical field [0001] The invention relates to a conjugated polymer electron donor material used in the blended active layer of a polymer solar cell, in particular to a two-dimensional benzodithiophene conjugated polymer containing a dithiol-substituted side chain Electron donor materials and methods for their preparation. Background technique [0002] Polymer solar cells (PSCs) have the characteristics of thinness, low manufacturing cost, etc., and can be processed into flexible devices by wet methods such as spin coating, printing, and inkjet printing, so they have become a hot spot in current energy research. However, the low efficiency and device instability of PSCs compared with inorganic solar cells are still the main obstacles to their commercialization. [0003] The most important part of developing high-efficiency PSCs is the research and development of polymer electron donor materials in the blended active layer, especially the spectral absorption range of the po...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12
CPCC08G61/126C08G2261/124C08G2261/18C08G2261/3223C08G2261/3243C08G2261/3246C08G2261/91
Inventor 唐卫华邓平尹新星俞江升
Owner NANJING UNIV OF SCI & TECH
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