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Benzodithiophene-benzodi(benzothiadiazole) containing copolymer, preparation and application thereof

A technology of benzothiadiazole and benzodithiophene is applied in the fields of benzodithiophene-benzodipolymer and its preparation and application, which can solve problems such as low energy conversion efficiency, achieve good thermal stability, The effect of good electron transport properties and good film-forming properties

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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  • Benzodithiophene-benzodi(benzothiadiazole) containing copolymer, preparation and application thereof
  • Benzodithiophene-benzodi(benzothiadiazole) containing copolymer, preparation and application thereof
  • Benzodithiophene-benzodi(benzothiadiazole) containing copolymer, preparation and application thereof

Examples

Experimental program
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Embodiment 1

[0062] A benzodithiophene-benzobis(benzothiadiazole) copolymer, namely poly{4,8-(dioctyl)oxy-benzo[1,2-b:4,5-b ']dithiophene-6,7-bis(3,7-dimethyloctyl)-benzo[2,1-e:3,4-e]bis(benzothiadiazole)} (n=55 ), denoted as copolymer P1, the general formula is as follows:

[0063]

[0064] The preparation method comprises the following steps:

[0065] (1), 4,9-dibromo-6,7-bis(3,7-dimethyloctyl)-benzo[2,1-e:3,4-e]bis(benzothiadiazole ) (B1) preparation method comprises the following steps:

[0066] (1) Preparation of compound 5-nitro-2,1,3 benzothiadiazole:

[0067]

[0068] Add 4-nitrobenzene-1,2-diamine (22.95g, 0.15mol) and 100mL thionyl chloride (SOCl 2 ), stirred and slowly added 2 mL of pyridine dropwise. At room temperature, 2-amino-5-nitroaniline was not completely dissolved, and the solution was orange. After heating, reflux at 80~90°C for 24 hours, stop the reaction, and heat to 80°C. Distill off excess thionyl chloride (SOCl 2 ), the reaction product was cooled to r...

Embodiment 2

[0090] A benzodithiophene-benzobis(benzothiadiazole) copolymer, poly{4,8-dioctyl-benzo[1,2-b:4,5-b']dithiophene- 6,7-bis(3,7-dimethyloctyl)-benzo[2,1-e:3,4-e]bis(benzothiadiazole)} (n=50), recorded as copolymerization Thing P2, general formula is as follows:

[0091]

[0092] The preparation method comprises the following steps:

[0093] (1) The preparation method of 4,8-dioctyl-2,7-di(tributyltinyl)-benzo[1,2-b:4,5-b']dithiophene (A2) is as follows:

[0094] Provide a compound C1 with a structural formula as shown in formula C1, namely 4,8-dioctyl-2,7-dibromo-benzo[1,2-b:4,5-b']dithiophene;

[0095] Compound C1 (11.46g, 0.02mol) and 100mL THF were added to a round bottom flask, and under nitrogen protection, the temperature was lowered to -78°C, and 16.8mL (2.5M, 0.04mol) of n-butyllithium in n-hexane was added dropwise, React for 1 hour, add 11.2mL tributyltin chloride (SnBu 3 Cl) (0.04mol), the temperature was raised to room temperature after 1 hour of reaction, and ...

Embodiment 3

[0102] A benzodithiophene-benzobis(benzothiadiazole) copolymer, that is, poly{4,8-bis(5'-hexadecyl-2'-thienyl)-benzo[1, 2-b:4,5-b']dithiophene-benzo[1,2-b:4,5-b']dithiophene-6,7-di(3,7-dimethyloctyl)- Benzo[2,1-e:3,4-e]bis(benzothiadiazole)} (n=85), denoted as copolymer P3, the general formula is as follows:

[0103]

[0104] The preparation method comprises the following steps:

[0105] (1), 4,8-bis(5'-hexadecyl-2'-thienyl)-2,7-bis(tributyltinyl)-benzo[1,2-b:4,5-b '] Dithiophene (A3) was prepared as follows:

[0106] Provide a compound C2 with a structural formula as shown in formula C2, namely 4,8-bis(5'-hexadecyl-2'-thienyl)-2,7-dibromo-benzo[1,2-b:4 ,5-b']dithiophene;

[0107] Add compound C2 (9.61g, 0.01mol) and 100mL THF into a round bottom flask, under nitrogen protection, cool down to -78°C, add dropwise 8.4mL (2.5M, 0.02mol) of n-butyllithium in n-hexane, React for 1 hour, add SnBu 3 Cl 5.60mL (0.02mol), reacted for 1 hour, then warmed up to room temperature,...

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Abstract

The invention provides a benzodithiophene-benzodi(benzothiadiazole) containing copolymer, preparation and application thereof. The benzodithiophene-benzodi(benzothiadiazole) containing copolymer is a compound P with a general formula shown as the specification, wherein R1 and R2 are alkyl of C1-C20, R3 and R4 are alkyl of C1-C20, alkoxy of C6-C16 or a thiophene derivative group, which has an alkyl side chain of C16, and n is an integer ranging from 1 to 100. The benzodithiophene-benzodi(benzothiadiazole) containing copolymer contains a new benzodi(benzothiadiazole) conjugated unit, the absorption spectrum of the copolymer undergoes red shift and has a high matching degree with a solar spectrum. Meanwhile, with a planar conjugated structure, the copolymer provided by the invention has the advantages of high charge carrier migration rate and high energy conversion efficiency, simple and controllable preparation method, and has good application prospects in polymer solar cells, organic light-emitting devices and other photoelectric material fields.

Description

technical field [0001] The invention relates to the technical field of photoelectric materials, in particular to a benzodithiophene-benzobis(benzothiadiazole) copolymer and its preparation 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 conjugated...

Claims

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Application Information

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