Bi-selenophen-benzodi(selenole)-containing copolymer as well as preparation method and application thereof

A technology of benzoselenodiazole and copolymers, which is applied in the field of copolymers containing diselenophene-benzodiazole and its preparation, can solve the problem of low energy conversion efficiency of organic solar cells, poor absorption spectrum and solar spectrum Ground matching, reducing the photon absorption rate in the solar spectrum, etc.

Inactive Publication Date: 2014-10-01
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

[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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  • Bi-selenophen-benzodi(selenole)-containing copolymer as well as preparation method and application thereof
  • Bi-selenophen-benzodi(selenole)-containing copolymer as well as preparation method and application thereof
  • Bi-selenophen-benzodi(selenole)-containing copolymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
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preparation example Construction

[0043] Such as figure 1 Shown, the preparation method of the copolymer containing diselenophene-benzo two (benzoselenodiazol) 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 , R 3 and R 4 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 , R 4 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 solutio...

Embodiment 1

[0108] This example discloses poly{4,4'-dioctyl-2,2'-diselenophene-6,7-bis(3,7-dimethyl)octyl-benzo[2 ,1-e:3,4-e]bis(benzoselenoadiazole)} (copolymer P1 containing diselenophene-benzobis(benzoselenoadiazole)):

[0109] Among them, n=50.

[0110] The preparation process of the above-mentioned copolymer P1 containing diselenophene-benzobis(benzoselenodiazole) is as follows:

[0111] Step 1. Preparation of 4,4'-dibromo-6,6'-diiodo-bi-2,1,3-benzoselenadiazole

[0112] 1.1. Preparation of compound 5-nitro-2,1,3 benzothiadiazole

[0113]

[0114] 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 produ...

Embodiment 2

[0144] This example discloses poly{4,4'-dimethyl-2,2'-diselenophene-6,7-bis(3,7-dimethyl)octyl-benzo[2 ,1-e:3,4-e]bis(benzoselenoadiazole)} (copolymer P2 containing diselenophene-benzobis(benzoselenoadiazole)):

[0145] Among them, n=20.

[0146] The preparation process of the above-mentioned copolymer P2 containing diselenophene-benzobis(benzoselenodiazole) is as follows:

[0147] Step 1. Preparation of 4,4'-dimethyl-5,5'-bis(tributyltinyl)-2,2'-diselenophene

[0148]

[0149] Under the protection of nitrogen, add 4,4'-dimethyl-5,5'-dibromo-2,2'-diselenophene (4.50g, 0.01mol) into the three-necked flask, add 50ml of tetrahydrofuran solvent , slowly inject n-butyllithium (8.6mL, 0.02mol) with a syringe at -78°C, continue stirring for 1.5h, inject tributyltin chloride (5.6mL, 0.02mol), after reacting for 1 hour, the temperature was raised to room temperature and the reaction was stirred for 6 hours. Saturated aqueous sodium chloride solution (30ml) was added to termina...

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Abstract

The invention provides a bi-selenophen-benzodi(selenole)-containing copolymer. The structural general formula is as shown in the specification, wherein R1, R2, R3 and R4 are alkyls from C1 to C20, and n is an integer from 1 to 100. The bi-selenophen-benzodi(selenole)-containing copolymer is narrower in energy gap. The invention also provides a preparation method of the bi-selenophen-benzodi(selenole)-containing copolymer and an organic solar battery device and an organic electroluminescent device which use the bi-selenophen-benzodi(selenole)-containing copolymer.

Description

technical field [0001] The invention relates to the field of optoelectronics, in particular to a copolymer containing diselenophene-benzobis(benzoselenodiazole), 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 c...

Claims

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Application Information

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