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Selenophen bithiophene-silole di (benzo thiadiazole) copolymer and its preparation and application

A technology of benzothiadiazole and phenbithiophene, which is applied in the field of selenium-containing phenbithiophene-thiarolodipolymer and its preparation, can solve the problems of low energy conversion efficiency and achieve narrow band gap and excellent carrier Migration ability and structural flexibility, the effect of broad application prospects

Inactive Publication Date: 2014-06-04
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

[0004] Copolymers containing thiophene units and benzothiadiazole units have been reported for optoelectronic materials, but the energy conversion efficiency obtained in practical applications is still low

Method used

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  • Selenophen bithiophene-silole di (benzo thiadiazole) copolymer and its preparation and application
  • Selenophen bithiophene-silole di (benzo thiadiazole) copolymer and its preparation and application
  • Selenophen bithiophene-silole di (benzo thiadiazole) copolymer and its preparation and application

Examples

Experimental program
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Effect test

Embodiment 1

[0066] A selenium-containing phenothiophene-thiarolobis(benzothiadiazole) copolymer, that is, poly{4,4'-dioctyl-2,2'-selenophenethiophene-6,6 dioctyl Thirolo[3,2-e:4,5-e]bis(benzothiadiazole)} (n=47), denoted as copolymer P1, the structural formula is as follows:

[0067]

[0068] The preparation method comprises the following steps:

[0069] (1), the preparation method of 4,9-dibromo-6,7-dioctyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole) (A1) includes the following Steps:

[0070]

[0071] (1) Preparation of compound 5-nitro-2,1,3 benzothiadiazole, the reaction formula is:

[0072]

[0073] Add 4-nitrobenzene-1,2-diamine (22.95g, 0.15mol) and 100ml of thionyl chloride into a three-necked flask, stir and slowly add 2ml of pyridine dropwise, heat and reflux at 80~90°C for 24h , stop the reaction, heat to 80°C and spin evaporate excess thionyl chloride, then cool the reaction product to room temperature, pour it into a large amount of water, stir, filter, wash with wate...

Embodiment 2

[0099] A selenium-containing phenene-thiophene-thiarolobis(benzothiadiazole) copolymer, that is, poly{4,4'-bis(n-eicosyl)-2,2'-selenophenethiophene-6 ,6 dimethylthiarolo[3,2-e:4,5-e]bis(benzothiadiazole)} (n=26), denoted as copolymer P2, the structural formula is as follows:

[0100]

[0101] The preparation method comprises the following steps:

[0102] (1), the preparation method of 6,6-dimethyl-4,8-dibromothiarolo[3,2-e:4,5-e]bis(benzothiadiazole) (A2) includes the following Steps:

[0103] 4,4'-dibromo-6,6'-diiodo-bi-2,1,3-benzothiadiazole was prepared according to steps (1)-(4) of step (1) of Example 1.

[0104] Compound C2, ie, dimethyldichlorosilane, having the structural formula shown in formula C2 is provided.

[0105] Add 4,4'-dibromo-6,6'-diiodo-bis-2,1,3-benzothiadiazole (3.4g, 5mmol) and 50ml DMF into a three-necked flask, blow nitrogen into it and stir for 20min, slowly Add 5.0mL of n-butyllithium n-hexane solution (2.5M, 0.01mol) dropwise, drop it in 0.5 ...

Embodiment 3

[0120] A selenium-containing phenothiophene-thiarolobis(benzothiadiazole) copolymer, that is, poly{4,4'-dioctyl-2,2'-selenophenethiophene-6,6 bis(n- Eicosyl)thiarolo[3,2-e:4,5-e]bis(benzothiadiazole)} (n=68), denoted as copolymer P3, the structural formula is as follows:

[0121]

[0122] The preparation method comprises the following steps:

[0123] (1), 6,6-bis(n-eicosyl)-4,8-dibromothiarolo[3,2-e:4,5-e]bis(benzothiadiazole) (A3) The preparation method comprises the following steps:

[0124] 4,4'-dibromo-6,6'-diiodo-bi-2,1,3-benzothiadiazole was prepared according to steps (1)-(4) of step (1) of Example 1.

[0125] A compound C3 having a structural formula as shown in the formula C3 is provided, that is, bis(n-eicosyl)dichlorosilane.

[0126] Add 4,4'-dibromo-6,6'-diiodo-bis-2,1,3-benzothiadiazole (3.4g, 5mmol) and 50ml DMF into a three-necked flask, blow nitrogen into it and stir for 20min, slowly Add 7.8mL of n-butyllithium (2.5M, 0.0195mol) dropwise, drop it over in ...

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Abstract

The invention provides a selenophen bithiophene-silole di (benzo thiadiazole) copolymer and its preparation and application, the selenophen bithiophene-silole di (benzo thiadiazole) copolymer is a compound P with the following general formula (shown in the specification), wherein R1 and R2 are C1-C20 alkyls, R 3 and R4 are H or C1-C20 alkyl, and n is an integer between 1-100. The selenophen bithiophene-silole di (benzo thiadiazole) copolymer contains a novel silole di (benzo thiadiazole) conjugated unit, is high in matching degree with solar spectrum, and is a plane conjugate structure, the charge carrier mobility rate is high, the energy conversion efficiency is improved, the preparation method is simple and controllable, and the selenophen bithiophene-silole di (benzo thiadiazole) copolymer has good application prospects in the fields of polymer solar cells, organic electroluminescent devices and other photoelectric materials.

Description

technical field [0001] The invention relates to the technical field of photoelectric materials, in particular to a selenium-containing phenbithiophene-thiarolobis(benzothiadiazole) 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 N.S. Sariciftci et al reported the light-induced electron transfer between conjugated polymers and C60 in SCIENC...

Claims

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Application Information

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IPC IPC(8): C08G61/12H01L51/46H01L51/54C07F7/10
CPCY02E10/549
Inventor 周明杰管榕黎乃元
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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