Biselenophen-benzobi(diazosulfide) copolymer and preparation method and application thereof

A benzothiadiazole and copolymer technology, which is used in semiconductor/solid-state device manufacturing, organic chemistry, electrical solid-state devices, etc., can solve problems such as limiting the scope of application, and achieve improved solubility and molecular weight. mature effect

Inactive Publication Date: 2014-05-21
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

[0006] However, there are still no literature and patent reports on polymers containing diselenophene-benzobis(benzothiadiazole) copolymers at the same time, which greatly limits its application range in fields such as solar cells.

Method used

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  • Biselenophen-benzobi(diazosulfide) copolymer and preparation method and application thereof
  • Biselenophen-benzobi(diazosulfide) copolymer and preparation method and application thereof
  • Biselenophen-benzobi(diazosulfide) copolymer and preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0039] The preparation method containing diselenophene-benzo two (benzothiadiazole) copolymers of the present invention comprises the following steps:

[0040] (1) In an inert gas environment, add 4,4'-dibromo-6,6'-diiodo-bis 2,1,3 benzothiadiazole, alkyne compound, first catalyst and base to the second In a solvent, react at 130° C. for 4 hours to obtain compound 3, the structural formula of which is

[0041] The molar ratio of the 4,4'-dibromo-6,6'-diiodo-linked 2,1,3 benzothiadiazole to the alkyne compound is 1:2, and the base is Bu 3 N, the molar ratio of the base to the alkyne compound is 1:1. The first catalyst is Pd(OAc) 2 (palladium acetate), the molar amount of the first catalyst is 4,4'-dibromo-6,6'-diiodo-linked 2,1,10% of 3-benzothiadiazole. The first solvent is DMF (N,N-dimethylformamide).

[0042] The reaction equation of this step is:

[0043]

[0044] (2) In an inert gas environment, add compound 4 to the second solvent, add butyllithium at -78°C for ...

Embodiment 1

[0055] The polymer of this example is: poly{2,2'-diselenophene-6,7-bis(3,7-dimethyl)octyl-benzo[2,1-e:3,4- e] bis(benzothiadiazole)}, having the structure of the formula:

[0056]

[0057] The preparation method of the polymer of the present embodiment comprises the following steps:

[0058] 1. Preparation of 4,4'-dibromo-6,6'-diiodo-linked 2,1,3 benzothiadiazole

[0059] (1) Preparation of 5-nitro-2,1,3 benzothiadiazole

[0060] In the three-necked flask, add 2-amino-5-nitroaniline (22.95g, 0.15mol) and 100ml thionyl chloride SOCl 2 , stirred and slowly added 2ml of pyridine dropwise, heated and refluxed at 80-90°C for 24 hours, stopped the 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 product 5-nitro-2,1,3-benzothiadiazole with a yield of 80%;

[0061]

[0062] (2) Preparat...

Embodiment 2

[0085] The polymer of this example is: poly{4,4'-didecyl-2,2'-diselenophene-6,7-bis(3,7-dimethyl)octyl-benzo[2 , 1-e:3,4-e]bis(benzothiadiazole)}, has the structure of the formula:

[0086]

[0087] The preparation method of the polymer of this embodiment comprises the following steps:

[0088] 1. Preparation of 4,9-dibromo-6,7-bis(3,7-dimethyl)octyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole)

[0089] Same as Step 2 of Example 1.

[0090] 2. Preparation of 4,4'-didecyl-5,5'-bis(tributyltin base)-2,2'-diselenophene

[0091] Under the protection of nitrogen, add 4,4'-didecyl-5,5'-dibromo-2,2'-diselenophene (6.98g, 0.01mol) into the three-necked flask, add 80ml of tetrahydrofuran solvent , and slowly inject n-butyllithium (8.4mL, 2.5M, 0.02mol) with a syringe at -78°C, continue stirring for 1h, and inject tributyltin chloride (5.6 mL, 0.02mol), reacted for 1 hour, then warmed up to room temperature and stirred for 6 hours. Saturated aqueous sodium chloride solution (30ml) wa...

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Abstract

The invention discloses a biselenophen-benzobi(diazosulfide) copolymer and a preparation method and an application thereof. The copolymer has a structure shown as a formula (I). The copolymer is prepared through carrying out a Stille coupling reaction on benzobi(diazosulfide) and biselenophen. The copolymer disclosed by the invention simultaneously contains biselenophen, benzobi(diazosulfide) and a novel benzobi(diazosulfide) conjugate unit to form a strong donor-receptor structure so as to improve the stability of the material and reduce the band gap of the material, thereby expanding the sunlight absorption range and improving the photoelectric conversion efficiency. According to the preparation method of the copolymer disclosed by the invention, the Stille reaction is a very mature polymerization reaction which is high in yield, mild in condition and easy to control.

Description

technical field [0001] The invention belongs to the technical field of organic materials. Specifically, the invention relates to a diselenophene-benzobis(benzothiadiazole) copolymer, a preparation method and application thereof. 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. 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, 1992,258,1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C07D513/04H01L51/54H01L51/56H01L51/46H01L51/48
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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