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Sulfothiazole-carbazole-benzodithiophene-containing copolymer and its preparation method and use

A benzodithiophene and thiothiazole-containing technology is applied in sustainable manufacturing/processing, semiconductor/solid-state device manufacturing, organic chemistry, etc., and can solve problems such as high cost, limited application, and complex production process

Active Publication Date: 2014-09-17
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently commercialized silicon solar cells are limited in application due to complex production process and high cost

Method used

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  • Sulfothiazole-carbazole-benzodithiophene-containing copolymer and its preparation method and use
  • Sulfothiazole-carbazole-benzodithiophene-containing copolymer and its preparation method and use
  • Sulfothiazole-carbazole-benzodithiophene-containing copolymer and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] A copolymer containing thiothiazole-carbazole-benzodithiophene, denoted as copolymer P1 (n=10), the structural formula is as follows:

[0067]

[0068] The preparation method comprises the following steps:

[0069] 1. Preparation of compound 2,6-bis(trimethyltin)-4,8-bis(4,5-dimethylmercapto-1,3-dithiol-2-aldehyde)benzo[1,2-b :4,5-b']dithiophene, denoted as A1;

[0070] (1) Preparation of compound 4,8-bis(4,5-dimethylmercapto-1,3-dithiol-2-aldehyde)benzo[1,2-b:4,5-b']dithiophene, Denote it as c1:

[0071] Provides compounds b1 and a, namely 2-dimethoxyphosphono-4,5-dimethylmercapto-1,3-dithiol and benzo[1,2-b:4,5-b']dithiophene- 4,8-diketone;

[0072] Under nitrogen protection, cool 1.22g (4.0mmol) b1 in 60mL of anhydrous THF to -78°C, slowly add 2.7mL of 1.5M LDA in cyclohexane (4mmol), and stir at -78°C for 3h , then add 0.44g (2.0mmol) a of 10mL anhydrous tetrahydrofuran solution to carry out Wittig-Horner reaction, keep warm for 0.5h and return to room tempe...

Embodiment 2

[0092] A copolymer containing thiothiazole-carbazole-benzodithiophene, denoted as copolymer P2 (n=60), the structural formula is as follows:

[0093]

[0094] The preparation method comprises the following steps:

[0095] 1. Preparation of compound 2,6-bis(trimethyltin)-4,8-bis(4,5-dioctylmercapto-1,3-dithiol-2-aldehyde)benzo[1,2-b :4,5-b']dithiophene, denoted as A2;

[0096] (1) Preparation of compound 4,8-bis(4,5-dioctylmercapto-1,3-dithiol-2-aldehyde)benzo[1,2-b:4,5-b']dithiophene, Denote it as c2:

[0097] Provides compounds b2 and a, namely 2-dimethoxyphosphono-4,5-dioctylmercapto-1,3-dithiol and benzo[1,2-b:4,5-b']dithiophene- 4,8-diketone;

[0098] Under nitrogen protection, cool 2.2g (4.4mmol) of b2 in 60mL of anhydrous tetrahydrofuran to -78°C, slowly add 4.0mL of 1.5M LDA in cyclohexane (6mmol), and stir at -78°C for 3h , then add 0.44g (2.0mmol) a of 10mL anhydrous tetrahydrofuran solution to carry out Wittig-Horner reaction, keep warm for 0.5h and return to...

Embodiment 3

[0116] A copolymer containing thiothiazole-carbazole-benzodithiophene, denoted as copolymer P3 (n=30), the structural formula is as follows:

[0117]

[0118] The preparation method comprises the following steps:

[0119] 1. Preparation of compound 2,6-bis(trimethyltin)-4,8-bis(4,5-bis(hexadecylmercapto)-1,3-dithiol-2-aldehyde)benzo[1, 2-b:4,5-b']dithiophene, denoted as A3;

[0120] (1) Preparation of compound 4,8-bis(4,5-bis(hexadecylmercapto)-1,3-dithiol-2-aldehyde)benzo[1,2-b:4,5-b'] Dithiophene, denoted as c3:

[0121] Provides compounds b3 and a, namely 2-dimethoxyphosphono-4,5-di(hexadecylmercapto)-1,3-dithiol and benzo[1,2-b:4,5-b'] Dithiophene-4,8-dione;

[0122] Under the protection of argon, cool the solution of 2.18g (3.0mmol) b3 in 60mL of anhydrous tetrahydrofuran to -78°C, slowly add 3.0mL of 1.5M LDA in cyclohexane (4.5mmol), and stir the reaction at -78°C After 2h, add 0.264g (1.2mmol) a of 15mL anhydrous tetrahydrofuran solution to carry out Wittig-Hor...

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Abstract

The invention provides a sulfothiazole-carbazole-benzodithiophene-containing copolymer and its preparation method and use. The sulfothiazole-carbazole-benzodithiophene-containing copolymer is a compound P having the structural formula shown in the description and in the structural formula, R1 represents H, C1-C16 straight chain or branched chain alkyl, or C1-C16 straight chain or branched chain alkylmercapto group, R2 represents C1-C12 straight chain or branched chain alkyl, or other groups shown in the description, R' represents C1-C12 straight chain or branched chain alkyl and n is an integer of 5-60. The sulfothiazole-carbazole-benzodithiophene-containing copolymer contains 4,8-bis(1,3-dithiol-2-aldehyde)benzo[1,2-b: 4,5-b']dithiophene derivative, sulfothiazole and carbazole units, has a high solar spectrum matching degree, has a high carrier migration rate, and improves energy conversion efficiency.

Description

technical field [0001] The invention relates to the technical field of photoelectric materials, in particular to a thiothiazole-carbazole-benzodithiophene copolymer and its preparation method and application. Background technique [0002] The preparation of low-cost and high-efficiency solar cells has always been a research hotspot and difficulty in the field of photovoltaics. Due to the complex production process and high cost of commercialized silicon solar cells, the application is limited. In order to reduce the cost and expand the scope of application, people have been looking for new solar cell materials for a long time. Polymer solar cells have excellent market prospects due to the advantages of low raw material prices, light weight, flexibility, simple production process, and large-area preparation by coating and printing. Since 1992, N.S. Sariciftci et al. reported on SCIENCE (N.S Sariciftci, L. Smilowitz, A.J. Heeger, et al. Science, 1992, 258, 1474) that conjuga...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C07D519/00C07D495/04H01L51/46H01L51/54H01L51/30
CPCY02E10/549Y02P20/10
Inventor 周明杰管榕李满园
Owner OCEANS KING LIGHTING SCI&TECH CO LTD