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Copolymer containing dibenzothiophene-silole-di(diazosulfide) as well as preparation and application thereof

A technology of benzothiadiazole and dithiophene, which is applied in the field of dithiophene-thiarolodipolymers and its preparation, can solve the problems of low energy conversion efficiency and achieve narrow band gap, strong conjugation properties, The effect of excellent carrier mobility and structural flexibility

Active 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] Conjugated polymers containing dithiophene 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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  • Copolymer containing dibenzothiophene-silole-di(diazosulfide) as well as preparation and application thereof
  • Copolymer containing dibenzothiophene-silole-di(diazosulfide) as well as preparation and application thereof
  • Copolymer containing dibenzothiophene-silole-di(diazosulfide) as well as preparation and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0066] A copolymer containing dithiophene-thiarolobis(benzothiadiazole), that is, poly{3-octyl[3,2-b]dithiophene-6,6 dioctylthiadiazole[3 , 2-e:4,5-e] bis(benzothiadiazole)} (n=52), 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 thionyl chloride into a three-necked flask, stir and slowly add 2mL pyridine dropwise, heat and then 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 water and then vacuum dr...

Embodiment 2

[0099] A copolymer containing dithiophene-thiarolobis(benzothiadiazole), that is, poly{3-n-eicosyl[3,2-b]dithiophene-6,6 dimethylsilole And [3,2-e:4,5-e]bis(benzothiadiazole)} (n=29), 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] According to the steps (1)-(4) of step (1) of Example 1, 4,4'-dibromo-6,6'-diiodo-bi-2,1,3-benzothiadiazole was prepared.

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

[0105] Add 4,4'-dibromo-6,6'-diiodo-bi-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 4.0mL of n-butyllithium n-hexane solution (2.5M, 0.01mol) dropwise, drop it over in 0.5 hours, control the t...

Embodiment 3

[0120] A copolymer containing dithiophene-thiarolobis(benzothiadiazole), that is, poly{[3,2-b]dithiophene-6,6 bis(n-eicosyl)thiadiazole[ 3,2-e:4,5-e]bis(benzothiadiazole)} (n=22), 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-bi-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 n-hexane solution (2.5M, 0.0195mol) dropwise, drop it over in 0.5 hours, ...

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Abstract

The invention provides a copolymer containing dibenzothiophene-silole-di(diazosulfide) as well as a preparation method and an application thereof. The copolymer containing dibenzothiophene-silole-di(diazosulfide) is a copolymer P with the general formula as shown in the specification, wherein R1 and R2 are C1-C20 alkyls, R3 is H or C1-C20 alkyls, and n is an integer between 1 and 100 in the formula. The copolymer containing the dibenzothiophene-silole-di(diazosulfide) disclosed by the invention contains a new silole-di(diazosulfide) conjugated unit, is high in matching degree with a solar spectrum, and simultaneously is in a planer conjugate structure, and high in vector migration rate, the energy conversion efficiency is improved, and the preparation method is simple and controllable, and has a good application prospect in the photoelectric material fields such as a polymer solar cell, an organic light-emitting device and the like.

Description

technical field [0001] The invention relates to the technical field of photoelectric materials, in particular to a dithiophene-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 1992, N.S.Sariciftci et al reported on SCIENCE (N.S Sariciftci, L.Smilowitz, A.J.Heeger, et al.Science, 1992, 258, 1474) that conjugated...

Claims

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Application Information

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IPC IPC(8): C08G61/12C07F7/10C09K11/06H01L51/46H01L51/54
CPCY02E10/549
Inventor 周明杰管榕黎乃元
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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