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Copolymer containing [3,4-b]dithiophene-benzobis(benzothiadiazole), preparation method and applications thereof

A technology of benzothiadiazole and dithiophene, which is applied in the field of a[3,4-b]dithiophene-benzodipolymer and its preparation, can solve the problems of low energy conversion efficiency and achieve broad application prospects , excellent reduction reversibility, excellent carrier mobility and structural flexibility

Inactive Publication Date: 2014-05-07
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

[0004] Conjugated polymers containing thiophene units and benzothiadiazole units for optoelectronic materials have been reported, but the energy conversion efficiency obtained in practical applications is still low. Therefore, it is necessary to develop new polymer materials and improve the efficiency of optoelectronic materials. The energy conversion efficiency is of great significance for the development of organic solar cells

Method used

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  • Copolymer containing [3,4-b]dithiophene-benzobis(benzothiadiazole), preparation method and applications thereof
  • Copolymer containing [3,4-b]dithiophene-benzobis(benzothiadiazole), preparation method and applications thereof
  • Copolymer containing [3,4-b]dithiophene-benzobis(benzothiadiazole), preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] A copolymer containing a[3,4-b]dithiophene-benzobis(benzothiadiazole), that is, poly{4-octyl[3,4-b]dithiophene-6,7-di (3,7-Dimethyl)octyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole)} (n=52), denoted as copolymer P1, the structural formula is as follows :

[0060]

[0061] The preparation method comprises the following steps:

[0062] 1. Preparation of monomeric compound 4,9-dibromo-6,7-bis(3,7-dimethyl)octyl-benzo[2,1-e:3,4-e]bis(benzothio Oxadiazole), the structural formula is as follows:

[0063]

[0064] (1) Preparation of compound 5-nitro-2,1,3 benzothiadiazole, the reaction formula is:

[0065]

[0066] Add 4-nitrobenzene-1,2-diamine (22.95g, 0.15mol) and 100ml SOCl into the three-necked flask 2 , Stir and slowly add 2ml of pyridine dropwise, o-phenylenediamine cannot be completely dissolved at room temperature, the solution is orange, after heating, reflux reaction at 90°C for 24h, distill off excess SOCl 2 Finally, the mixture was cooled to room tempera...

Embodiment 2

[0091] A copolymer containing [3,4-b]dithiophene-benzobis(benzothiadiazole), that is, poly{4-n-eicosyl[3,4-b]dithiophene-6- Methyl-7-propyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole)} (n=24), denoted as copolymer P2, the structural formula is as follows:

[0092]

[0093] 1. Preparation of compound 4,9-dibromo-6-methyl-7-propyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole);

[0094] To prepare the compound 4,4'-dibromo-6,6'-diiodo-bi-2,1,3 benzothiadiazole, the steps (1)~(4) are the same as the steps (1)~( 4) the same.

[0095] (5) Preparation of compound 4,9-dibromo-6-methyl-7-propyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole), the reaction formula is:

[0096]

[0097] Add 4,4'-dibromo-6,6'-diiodo-bi-2,1,3 benzothiadiazole (6.8g, 10mmol) and 2-hexyne (1.64g, 20mmol) into the three-necked flask , 50ml DMF, stirred with nitrogen gas for 20min, added Bu 3 N (1.814g, 20mmol) and Pd(OAc) 2 (230mg, 1.0mmol), heated to 130°C, reacted at constant temperature for 4h, cooled, washed wit...

Embodiment 3

[0110] A kind of [3,4-b]dithiophene-benzobis(benzothiadiazole) copolymer, that is, poly{[3,4-b]dithiophene-6-(3,7-dimethyl base) octyl-7-n-eicosylbenzo[2,1-e:3,4-e]bis(benzothiadiazole)} (n=20), denoted as copolymer P3, the structural formula is as follows :

[0111]

[0112] 1. Preparation of compound 4,9-dibromo-6-(3,7-dimethyl)octyl-7-n-eicosyl-benzo[2,1-e:3,4-e]bis( benzothiadiazole);

[0113]Preparation of compound 4,4'-dibromo-6,6'-diiodo-bi-2,1,3 benzothiadiazole, its steps (1)~(4) are the same as those in step 1 of Example 1 (1) ~(4) is the same.

[0114] (5) Preparation of 4,9-dibromo-6-(3,7-dimethyl)octyl-7-n-eicosyl-benzo[2,1-e:3,4-e]bis( benzothiadiazole), the reaction formula is:

[0115]

[0116] Add 4,4'-dibromo-6,6'-diiodo-bi-2,1,3 benzothiadiazole (6.8g, 10mmol) into the three-necked flask, add 2,6 dimethyl-9-tri Decyne (8.94g, 20mmol), 80ml DMF, stirred with nitrogen for 20min, added Bu 3 N (1.814g, 20mmol) and Pd(OAc) 2 (230mg, 1.0mmol), heated...

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Abstract

The invention provides a copolymer containing [3,4-b]dithiophene-benzobis(benzothiadiazole), a preparation method and applications thereof. The structural formula of the copolymer is represented in the description as a compound P, in the structural formula, the R1 and R2 are individually selected from C1-C20 alkyl groups, the R3 is selected from H group or C1-C20 alkyl groups, and n is an integer in a range of 1 to 100. The copolymer comprises a novel benzobis(benzothiadiazole) conjugated unit, thus the absorption spectrum of the copolymer has red shift phenomenon and has a high matching degree with the sunlight spectrum, the carrier migration speed and the energy conversion efficiency are improved, the preparation method of the copolymer is simple and controllable, so that the copolymer has a very good application prospect in the fields of polymer solar cells and organic electroluminescence devices. The structure formula of the copolymer is represented in the description.

Description

technical field [0001] The invention relates to the technical field of photoelectric materials, in particular to a [3,4-b]dithiophene-benzobis(benzothiadiazole) copolymer and 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, the application is 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, 1474) ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46H01L51/54C07D519/00
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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