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Copolymer containing dithiophenepyrrole-benzobis(benzothiadiazole), preparation method thereof and applications thereof

A technology of benzothiadiazole and dithiophene pyrrole, which is applied in the field of organic semiconductor materials, can solve problems such as limiting the application range, and achieve the effects of expanding the absorption range, improving stability, improving solubility and molecular weight

Inactive Publication Date: 2014-03-12
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

[0006] However, there are still no literature and patent reports for the copolymer containing dithiophene pyrrole-benzobis(benzothiadiazole), which greatly limits its scope of application.

Method used

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  • Copolymer containing dithiophenepyrrole-benzobis(benzothiadiazole), preparation method thereof and applications thereof
  • Copolymer containing dithiophenepyrrole-benzobis(benzothiadiazole), preparation method thereof and applications thereof
  • Copolymer containing dithiophenepyrrole-benzobis(benzothiadiazole), preparation method thereof and applications thereof

Examples

Experimental program
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preparation example Construction

[0033] The present invention also provides a preparation method for the above-mentioned copolymer containing dithiophene pyrrole-benzobis(benzothiadiazole), comprising the steps of:

[0034] S1, the preparation structural formula is Compound A (i.e. 5-nitro-2,1,3-benzothiadiazole):

[0035] 1. The structural formula is Compound I (4-nitrobenzene-1,2-diamine) was added to thionyl chloride, stirred and added to thionyl chloride (structural formula is ) was added dropwise pyridine (the structural formula is Molecular formula is C 5 h 5 N,), reflux reaction at 85 ° C, stop the reaction, the obtained structural formula is Compound F (that is, 5-nitro-2,1,3 benzothiadiazole); the reaction formula is as follows:

[0036]

[0037] Compound F is preferably purified by:

[0038] Heating the reaction solution to 80°C and rotary evaporating excess SOCl 2 Afterwards, the reaction product was cooled to room temperature, poured into a large amount of water, stirred, filtered,...

Embodiment 1

[0066] The copolymer containing dithiophene pyrrole-benzobis(benzothiadiazole) in this example, that is, poly{N-octyl-dithieno[3,2-b:2',3'-b'] Pyrrole-6,7-bis(3,7-dimethyl)octyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole)}, its structural formula is as follows:

[0067]

[0068] The preparation process is as follows:

[0069] 1. Preparation of 4,4'-dibromo-6,6'-diiodo-bi-2,1,3-benzothiadiazole

[0070] 1. Preparation of compound 5-nitro-2,1,3 benzothiadiazole

[0071]

[0072] 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 85°C for 24h, stop Reaction, heated to 80 °C and rotary evaporated excess SOCl 2 Finally, the reaction product was cooled to room temperature, poured into a large amount of water, stirred, filtered, washed with water and then dried in vacuum to obtain 21.7 g of the purified product 5-nitro-2,1,3-benzothiadiazole with a yield of 80%...

Embodiment 2

[0091] The copolymer containing dithiophenepyrrole-benzobis(benzothiadiazole) in this example, that is, poly{N-decyl-dithieno[3,2-b:2',3'-b'] Pyrrole-6,7-bis(3,7-dimethyl)octyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole)}, its structural formula is as follows:

[0092]

[0093] The preparation process is as follows:

[0094] 1. Preparation of 4,4'-dibromo-6,6'-diiodo-bi-2,1,3 benzothiadiazole This step 1 is the same as step 1 in Example 1.

[0095] Two, 4,9-dibromo-6,7-bis(3,7-dimethyl)octyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole) preparation

[0096] This step two is the same as step two of embodiment 1.

[0097] 3. Preparation of N-decyl-2,6-di(tributyltin)-dithieno[3,2-b:2',3'-b']pyrrole

[0098]

[0099] Under the protection of nitrogen, N-decyl-2,6-dibromo-dithieno[3,2-b:2',3'-b']pyrrole (7.16g, 0.015mol ), add 100ml of tetrahydrofuran solvent, slowly inject n-butyllithium (12.6mL, 2.5M, 0.03mol) with a syringe at -78°C, continue stirring for 2h, inject three Buty...

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Abstract

The invention belongs to the field of organic semiconductor materials, and discloses a copolymer containing dithiophenepyrrole-benzobis(benzothiadiazole), a preparation method thereof and applications thereof. The copolymer has a general structure formula as follows, wherein R1, R2 and R3 are the same or different C1-C20 alkyl; and n is an integer between 1 and 100. According to the copolymer, the benzobis(benzothiadiazole) is an excellent donor material. The benzobis(benzothiadiazole) has advantages of simple structure, symmetry, good electron delocalization performances, and the like, has a plane structure and is an excellent receptor material. The copolymer formed by the dithiophenepyrrole and the benzobis(benzothiadiazole) can form a strong electron donor-receptor structure, thus facilitating reduction of the energy band gap of a material, thereby expanding the sunlight adsorption scope and increasing the photoelectric conversion rate.

Description

technical field [0001] The invention relates to organic semiconductor materials, in particular to a copolymer containing dithiophene pyrrole-benzobis(benzothiadiazole), 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, their applications are 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. Copolymer 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 c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K11/06H01L51/46H01L51/54
CPCY02E10/549
Inventor 周明杰管榕黎乃元黄佳乐李满园
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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