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Copolymer containing 2, 7-carbazole benzo-bi(diazosulfide) and preparation method and application thereof

A benzothiadiazole and copolymer technology, which is applied in the field of 2,7-carbazole-benzodi-containing copolymer and its preparation, can solve the problems of limiting the application range and the like, and achieves the expansion of the solar light absorption range and the improvement of the Effects of stability, improved solubility and molecular weight

Inactive Publication Date: 2014-03-26
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] However, there are still no literature and patent reports for the copolymer containing 2,7-carbazole-benzobis(benzothiadiazole) at the same time, which greatly limits its scope of application.

Method used

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  • Copolymer containing 2, 7-carbazole benzo-bi(diazosulfide) and preparation method and application thereof
  • Copolymer containing 2, 7-carbazole benzo-bi(diazosulfide) and preparation method and application thereof
  • Copolymer containing 2, 7-carbazole benzo-bi(diazosulfide) and preparation method and application thereof

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preparation example Construction

[0034] The present invention also provides the preparation method of the above-mentioned copolymer containing 2,7-carbazole-benzobis(benzothiadiazole), comprising the steps of:

[0035] S1, the preparation structural formula is Compound A (i.e. 5-nitro-2,1,3-benzothiadiazole):

[0036] 1. The structural formula is Compound I (4-nitrobenzene-1,2-diamine) was added in 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:

[0037]

[0038] Compound F is preferably purified by:

[0039] 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, washed...

Embodiment 1

[0069] The copolymer containing 2,7-carbazole-benzobis(benzothiadiazole) of this embodiment, that is, poly{9-octyl-2,7-carbazole-6,7-bis(3,7 -Dimethyl)octyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole)}, whose structural formula is as follows:

[0070]

[0071] The preparation process is as follows:

[0072] 1. Preparation of 4,4'-dibromo-6,6'-diiodo-bi-2,1,3-benzothiadiazole

[0073] 1. Preparation of compound 5-nitro-2,1,3 benzothiadiazole

[0074]

[0075] 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 dried in vacuum to obtain 21.7 g of the purified product 5-nitro-2,1,3-benzothiadiazole with a yield of 80%;

[0076] 2. Preparati...

Embodiment 2

[0096] The copolymer containing 2,7-carbazole-benzobis(benzothiadiazole) of this embodiment, that is, poly{9-methyl-2,7-carbazole-6-(3,7-dimethyl base) octyl-7-n-eicosyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole)}, its structural formula is as follows:

[0097]

[0098] The preparation process is as follows:

[0099] 1. Preparation of 4,4'-dibromo-6,6'-diiodo-bi-2,1,3-benzothiadiazole

[0100] This step one is the same as step one in embodiment 1.

[0101] Two, 4,9-dibromo-6-(2,7-dimethyl)octyl-7-eicosylbenzo[2,1-e:3,4-e]bis(benzothiadi azole) preparation

[0102]

[0103] Add 4,4'-dibromo-6,6'-diiodo-bi-2,1,3 benzothiadiazole (3.4g, 5mmol) into the three-necked flask, add 2,6 dimethyl-9-tri Decyne (4.47g, 10mmol), 25ml DMF, stirred with nitrogen for 20min, added Bu 3 N (0.907g, 10mmol) and Pd(OAc) 2 (115mg, 0.5mmol), heated to 150°C, heated for ring closure reaction for 2 hours, cooled, washed with water, extracted with dichloromethane to obtain an organic layer, dri...

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Abstract

The invention belongs to the field of organic semiconductor materials, and discloses a copolymer containing 2, 7-carbazole benzo-bi(diazosulfide) and a preparation method and application thereof. The copolymer has the structural general formula shown in the specification, wherein R1, R2 and R3 respectively represent the same or different alkyl of C1-C20, and n is an integer between 1 and 100. According to the copolymer containing 2, 7-carbazole benzo-bi(diazosulfide), 2, 7-carbazole is a very excellent donor material; benzo-bi(diazosulfide) has advantages of simple and symmetrical structure and good electron delocalization performance, has a planar structure, and is a very excellent acceptor material; the copolymer formed by 2, 7-carbazole and benzo-bi(diazosulfide) has a very strong donor-acceptor structure, and is beneficial to lowering the energy band gap of materials so as to expand sunlight absorption range and improve photoelectric converting efficiency.

Description

technical field [0001] The invention relates to organic semiconductor materials, in particular to a copolymer containing 2,7-carbazole-benzobis(benzothiadiazole), its preparation method and application. Background technique [0002] Organic solar cells are a new type of solar cells. Compared with inorganic semiconductor materials, which are limited in source, expensive, toxic, complex preparation process, and high cost, etc., it has some advantages that inorganic solar cells cannot match, such as a wide range of material sources, Structural diversity and controllability, low cost, safety and environmental protection, simple manufacturing process, light product weight, large-area flexible preparation, etc., can be widely used in various fields such as construction, lighting and power generation, and has important development and application prospect. Therefore, many research institutions and enterprises at home and abroad have given considerable attention and investment. Ho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/54H01L51/46
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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