A kind of copolymer containing benzodithiophene-thiarolobis(benzothiadiazole) and its preparation and application

A technology of benzothiadiazole and benzodithiophene, which is applied in the field of benzodithiophene-thirolodicopolymer and its preparation, can solve the problems of low energy conversion efficiency and the like, and achieves narrow band gap and good electron affinity. Resultant force and electron mobility, promising effect

Active Publication Date: 2016-01-27
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Conjugated polymers containing benzodithiophene 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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  • A kind of copolymer containing benzodithiophene-thiarolobis(benzothiadiazole) and its preparation and application
  • A kind of copolymer containing benzodithiophene-thiarolobis(benzothiadiazole) and its preparation and application
  • A kind of copolymer containing benzodithiophene-thiarolobis(benzothiadiazole) and its preparation and application

Examples

Experimental program
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Effect test

Embodiment 1

[0067] A benzodithiophene-thiarolobis(benzothiadiazole) copolymer, namely poly{4,5-dioctylbenzo[2,1-b:3,4-b']dithiophene -6,6 Dioctylthiarolo[3,2-e:4,5-e]bis(benzothiadiazole)} (n=50), denoted as copolymer P1, the structural formula is as follows:

[0068]

[0069] The preparation method comprises the following steps:

[0070] (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:

[0071]

[0072] (1) Preparation of compound 5-nitro-2,1,3 benzothiadiazole, the reaction formula is:

[0073]

[0074] 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 vacuum...

Embodiment 2

[0100] A benzodithiophene-thiarolobis(benzothiadiazole) copolymer, namely poly{4,5-dioctyloxy-benzo[2,1-b:3,4-b'] Dithiophene-6,6-dioctylthiarolo[3,2-e:4,5-e]bis(benzothiadiazole)} (n=48), which is denoted as copolymer P2, and its structural formula is as follows:

[0101]

[0102] The preparation method comprises the following steps:

[0103] (1) Preparation of 6,6-dioctyl-4,8-dibromothiarolo[3,2-e:4,5-e]bis(benzothiadiazole) (A1)

[0104] The specific operation is the same as step (1) in Example 1.

[0105] (2), the preparation method of 4,5-dioctyloxy-2,7-bis(tributyltin base)-benzo[2,1-b:3,4-b']dithiophene (B2) includes the following step:

[0106] Provide a compound D2 with a structural formula as shown in formula D2, namely 4,5-dioctyloxy-2,7-dibromobenzo[2,1-b:3,4-b']dithiophene;

[0107] Under the protection of nitrogen, compound D2 (6.05g, 0.01mol) and 65mL of tetrahydrofuran were added to the three-necked flask, and 8.0mL of n-butyl lithium in n-hexane (2.5M, ...

Embodiment 3

[0115] A benzodithiophene-thiarolobis(benzothiadiazole) copolymer, namely poly{4,5-bis(n-eicosyl)-benzo[2,1-b:3,4 -b']dithiophene-6,6-dimethylthiarolo[3,2-e:4,5-e]bis(benzothiadiazole)} (n=29), denoted as copolymer P3, The structural formula is as follows:

[0116]

[0117] The preparation method comprises the following steps:

[0118] (1), the preparation method of 6,6-dimethyl-4,8-dibromothiarolo[3,2-e:4,5-e]bis(benzothiadiazole) (A2) includes the following Steps:

[0119] 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.

[0120] Compound C2, ie, dimethyldichlorosilane, having the structural formula shown in formula C2 is provided.

[0121] Add 4,4'-dibromo-6,6'-diiodo-bi2,1,3 benzothiadiazole (3.4g, 5mmol) and 50mL DMF into a three-necked flask, stir for 20min with nitrogen gas, and slowly drop Add 4.0mL of n-butyllithium n-hexane solution (2.5M, 0.01mol), drop it over in 0.5 hours, control the...

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Abstract

The invention provides a copolymer containing benzothiophene-silole di(diazosulfide) and a preparation method and application thereof. The copolymer containing benzothiophene-silole di(diazosulfide) is a copolymer P with a general formula shown in the specification, wherein R1 and R2 are C1-20 alkyl, R3 and R4 are C1-20 alkyl or C1-20 alkoxyl, and n is an integer from 1 to 100. The copolymer containing benzothiophene-silole di(diazosulfide) provided by the invention comprises a new silole di(diazosulfide) conjugating unit, has high matching rate with a solar spectrum. Meanwhile, the copolymer is in a planar conjugated structure and the carrier migration rate is high, so that the energy conversion ratio is improved. The preparation method is simple and controllable. The copolymer has a very good application prospect in the photoelectric material fields such as polymer solar batteries and organic electroluminescent apparatuses.

Description

technical field [0001] The invention relates to the technical field of photoelectric materials, in particular to a benzodithiophene-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...

Claims

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Application Information

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