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Copolymer containing dithieno (3,2-b:2',3'-d) thiophene-silole (2,3-b:3',2'-d) (diazosulfide) as well as preparation method and application of copolymer

A technology of benzothiadiazole and thiatrithiophene is applied in the field of copolymers containing thorylthiophene-thirolodiene and its preparation, which can solve the problems of low energy conversion efficiency and the like, and achieve strong conjugation properties and good electron affinity. Effect of resultant force and electron mobility, broad spectral response

Active Publication Date: 2014-06-04
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 trithiophene units and benzothiadiazole units have been reported for optoelectronic materials, but the energy conversion efficiency obtained in practical applications is still low

Method used

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  • Copolymer containing dithieno (3,2-b:2',3'-d) thiophene-silole (2,3-b:3',2'-d) (diazosulfide) as well as preparation method and application of copolymer
  • Copolymer containing dithieno (3,2-b:2',3'-d) thiophene-silole (2,3-b:3',2'-d) (diazosulfide) as well as preparation method and application of copolymer
  • Copolymer containing dithieno (3,2-b:2',3'-d) thiophene-silole (2,3-b:3',2'-d) (diazosulfide) as well as preparation method and application of copolymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] A copolymer containing trithiophene-thiarolobis(benzothiadiazole), that is, poly{3,5-dioctyl[3,2-b:4,5-b']trithiophene-6 , 6-dioctylthiarolo[3,2-e:4,5-e]bis(benzothiadiazole)} (n=53), denoted as copolymer P1, the structural formula is as follows:

[0067]

[0068] The preparation method comprises the following steps:

[0069] (1), the preparation method of 4,9-dibromo-6,7-dioctyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole) (A1) includes the following Steps:

[0070]

[0071] (1) Preparation of compound 5-nitro-2,1,3 benzothiadiazole, the reaction formula is:

[0072]

[0073] Add 4-nitrobenzene-1,2-diamine (22.95g, 0.15mol) and 100mL thionyl chloride into a three-necked flask, stir and slowly add 2mL pyridine dropwise, heat and then reflux at 80~90°C for 24h , stop the reaction, heat to 80°C and spin evaporate excess thionyl chloride, then cool the reaction product to room temperature, pour it into a large amount of water, stir, filter, wash with water and then ...

Embodiment 2

[0099] A copolymer containing trithiophene-thiarolobis(benzothiadiazole), that is, poly{3,5-bis(n-eicosyl)do[3,2-b:4,5-b' ]trithiophene-6,6-dimethylthiarolo[3,2-e:4,5-e]bis(benzothiadiazole)} (n=29), denoted as copolymer P2, the structural formula is as follows:

[0100]

[0101] The preparation method comprises the following steps:

[0102] (1), the preparation method of 6,6-dimethyl-4,8-dibromothiarolo[3,2-e:4,5-e]bis(benzothiadiazole) (A2) includes the following Steps:

[0103] According to the steps (1)-(4) of step (1) of Example 1, 4,4'-dibromo-6,6'-diiodo-bi-2,1,3-benzothiadiazole was prepared.

[0104] Compound C2, ie, dimethyldichlorosilane, having the structural formula shown in formula C2 is provided.

[0105] Add 4,4'-dibromo-6,6'-diiodo-bi-2,1,3-benzothiadiazole (3.4g, 5mmol) and 50mL DMF into a three-necked flask, blow nitrogen into it and stir for 20min, slowly Add 4.0mL of n-butyllithium n-hexane solution (2.5M, 0.01mol) dropwise, drop it over in 0.5 hour...

Embodiment 3

[0120] A copolymer containing trithiophene-thiarolobis(benzothiadiazole), that is, poly{3,5-dioctyl[3,2-b:4,5-b']trithiophene-6 , 6 bis(n-eicosyl)thiarolo[3,2-e:4,5-e]bis(benzothiadiazole)} (n=65), denoted as copolymer P3, the structural formula is as follows:

[0121]

[0122] The preparation method comprises the following steps:

[0123] (1), 6,6-bis(n-eicosyl)-4,8-dibromothiarolo[3,2-e:4,5-e]bis(benzothiadiazole) (A3) The preparation method comprises the following steps:

[0124] 4,4'-dibromo-6,6'-diiodo-bi-2,1,3-benzothiadiazole was prepared according to steps (1)-(4) of step (1) of Example 1.

[0125] A compound C3 having a structural formula as shown in the formula C3 is provided, that is, bis(n-eicosyl)dichlorosilane.

[0126] Add 4,4'-dibromo-6,6'-diiodo-bi-2,1,3-benzothiadiazole (3.4g, 5mmol) and 50mL DMF into a three-necked flask, blow nitrogen into it and stir for 20min, slowly Add 8.0 mL of n-butyllithium n-hexane solution (2.5M, 0.02) dropwise, drop it over 0...

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Abstract

The invention provides a copolymer containing dithieno (3,2-b:2',3'-d) thiophene-silole (2,3-b:3',2'-d) (diazosulfide) as well as a preparation method and an application of the copolymer. The copolymer provided by the invention is a copolymer P which has the general formula shown in the specification, wherein in the formula, R1 and R2 represent alkyl groups of C1 to C20; R3 and R4 represent H or alkyl groups of C1 to C20; n represents an integer between 1 and 100. The copolymer contains a new silole (2,3-b:3',2'-d) (diazosulfide) conjugation unit which has a high matching degree with solar spectrum and is of a plane conjugation structure at the same time, so that the charge carrier migration rate is high. Thus, the energy conversion efficiency is improved. A preparation method of the copolymer is simple and controllable. As a result, the copolymer provided by the invention has good application prospects in the fields of polymer solar cells, organic electroluminescent devices and other photoelectric materials.

Description

technical field [0001] The invention relates to the technical field of photoelectric materials, in particular to a trithiophene-thiarolobis(benzothiadiazole) copolymer and 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, 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) that conjugate...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12H01L51/46H01L51/54C07F7/10
CPCY02E10/549
Inventor 周明杰管榕黎乃元
Owner OCEANS KING LIGHTING SCI&TECH CO LTD
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