Copolymer containing thiophene-benzo-bi(benzo selenium diazole) as well as preparation method and application thereof

A technology of benzoselenodiazole and copolymers, which is applied in the field of thiophene-benzodiazole-containing copolymers and its preparation, can solve the problem that the absorption spectrum does not match well with the solar spectrum, reduces the photon absorption rate in the solar spectrum, Problems such as low energy conversion efficiency of organic solar cells

Inactive Publication Date: 2014-10-01
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Description
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  • Application Information

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Problems solved by technology

[0004] However, the energy band gap (the energy level difference between the HOMO energy level and the LUMO energy level) of traditional polymers is wide, and the absorption spectrum cannot match the solar spectrum well, which reduces the absorption rate of photons in the solar spectrum, thus making Energy conversion efficiency of organic solar cells using conventional polymers is low

Method used

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  • Copolymer containing thiophene-benzo-bi(benzo selenium diazole) as well as preparation method and application thereof
  • Copolymer containing thiophene-benzo-bi(benzo selenium diazole) as well as preparation method and application thereof
  • Copolymer containing thiophene-benzo-bi(benzo selenium diazole) as well as preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0043] like figure 1 Shown, the preparation method of the copolymer containing thiophene-benzo two (benzoselenadiazole) of one embodiment, comprises the steps:

[0044] Step S100, providing compound A and compound B.

[0045] Compound A and Compound B have the following structural formulas respectively:

[0046] A is: B is: Among them, R 1 , R 2 and R 3 for C 1 ~C 20 of alkyl.

[0047] The preparation of compound A comprises the following steps:

[0048] Step S111, providing compound C, n-butyllithium and tributyltin chloride.

[0049] The structural formula of compound C is where R 3 for C 1 ~C 20 of alkyl.

[0050] Step S112, under a protective gas atmosphere, add compound C into tetrahydrofuran, and add n-butyllithium (CH 3 (CH 2 ) 3 Li), stirred for 1 hour to 2 hours, and added tributyltin chloride (SnBu 3 Cl), react at -78°C for 1 hour, warm up to room temperature and stir for 6 hours, add saturated aqueous sodium chloride solution to terminate the r...

Embodiment 1

[0107] This example discloses poly{3-octylthiophene-6,7-bis(3,7-dimethyl)octyl-benzo[2,1-e:3,4-e]bis( benzoselenodiazole)} (copolymer P1 containing thiophene-benzobis(benzoselenodiazole)):

[0108] Among them, n=52.

[0109] The preparation process of the above-mentioned copolymer P1 containing thiophene-benzobis(benzoselenodiazole) is as follows:

[0110] Step 1. Preparation of 4,4'-dibromo-6,6'-diiodo-bi-2,1,3-benzoselenadiazole

[0111] 1.1. Preparation of compound 5-nitro-2,1,3 benzothiadiazole

[0112]

[0113] 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 24h, 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 then vacuum-dried to obtain 21.7 g of the product 5-nitro-2,1,3-benzothi...

Embodiment 2

[0143] This embodiment discloses poly{3-methylthiophene-6,7-bis(3,7-dimethyl)octyl-benzo[2,1-e:3,4-e]bis( Benzoselenadiazole)} (copolymer P2 containing thiophene-benzobis(benzoselenadiazole)):

[0144] Among them, n=24.

[0145] The preparation process of the above-mentioned copolymer P2 containing thiophene-benzobis(benzoselenodiazole) is as follows:

[0146] Step 1. Preparation of 3-methyl-2,5-bis(tributyltin)thiophene

[0147]

[0148] Under the protection of nitrogen, add 3-methyl-2,5-dibromothiophene (2.56g, 0.01mol) into the three-necked flask, add 60ml of tetrahydrofuran solvent, and slowly inject the positive Butyllithium (8.6mL, 2.5M, 0.02mol), continue to stir the reaction for 1.5h, inject tributyltin chloride (5.6mL, 0.02mol) with a syringe at -78°C, react for 1 hour and then warm to room temperature The reaction was stirred for 6 hours. Saturated aqueous sodium chloride solution (30ml) was added to terminate the reaction, extracted with anhydrous ether, dr...

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Abstract

The invention provides a copolymer containing thiophene-benzo-bi(benzo selenium diazole). The structural formula of the copolymer is as shown in the specification, and in the structural formula, R1, R2 and R3 are alkyl of C1-C20, and n is an integer from 1 to 100. The energy gap of the copolymer containing thiophene-benzo-bi(benzo selenium diazole is relatively narrow. The invention further provides a preparation method of the copolymer containing thiophene-benzo-bi(benzo selenium diazole, and an organic solar battery device and an organic electroluminescence device adopting the copolymer containing thiophene-benzo-bi(benzo selenium diazole.

Description

technical field [0001] The invention relates to the field of optoelectronics, in particular to a copolymer containing thiophene-benzobis(benzoselenadiazole), 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. [0003] 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 conju...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C07D517/04C07D519/00H01L51/46H01L51/54
CPCY02E10/549
Inventor 周明杰管榕黎乃元
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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