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

A benzothiadiazole and copolymer technology is applied in the field of fluorene-benzodipolymer and its preparation, which can solve the problems of low energy conversion efficiency and the like, and achieve good thermal stability, good electron transport properties, and good performance. membranous effect

Inactive Publication Date: 2014-05-07
OCEANS KING LIGHTING SCI&TECH CO LTD +2
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

[0004] Conjugated polymers containing fluorene 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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  • Fluorene-benzodi(benzothiadiazole) containing copolymer, preparation method and application thereof
  • Fluorene-benzodi(benzothiadiazole) containing copolymer, preparation method and application thereof
  • Fluorene-benzodi(benzothiadiazole) containing copolymer, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] A fluorene-benzobis(benzothiadiazole) copolymer, that is, poly{9,9-di-n-octylfluorene-6,7-bis(3,7-dimethyloctyl)-benzo [2,1-e:3,4-e]bis(benzothiadiazole)} (n=48), denoted as copolymer P1, the structural formula is as follows:

[0063]

[0064] The preparation method comprises the following steps:

[0065] (1) The preparation method of 4,9-dibromo-6,7-dioctyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole) (A1) is as follows:

[0066]

[0067] (1) Preparation of compound 5-nitro-2,1,3 benzothiadiazole, the reaction formula is:

[0068]

[0069] 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, at room temperature 4-nitrobenzene-1, The 2-diamine is not completely dissolved, and the solution is orange. After heating, reflux reaction at 80~90°C for 24 hours, stop the reaction, heat to 80°C and rotate to evaporate excess thionyl chloride, then cool the reaction product to room ...

Embodiment 2

[0095] A fluorene-benzobis(benzothiadiazole) copolymer, namely poly{9,9-di(n-dodecyl)fluorene-6-(3,7-dimethyl)octyl-7 -Hexacyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole)} (n=84), denoted as copolymer P2, the structural formula is as follows:

[0096]

[0097] The preparation method comprises the following steps:

[0098] (1), 4,9-dibromo-6-(3,7-dimethyl)octyl-7-hexadecyl-benzo[2,1-e:3,4-e]bis( Benzothiadiazole) (A2) is prepared as follows:

[0099] 4,4'-dibromo-6,6'-diiodo-bi-2,1,3-benzothiadiazole was prepared according to steps (1)-(4) of step (1) of Example 1.

[0100] A compound C2 having a structural formula as shown in formula C2 is provided, namely 2,6-dimethyl-11-hexahexyne.

[0101] Add 4,4'-dibromo-6,6'-diiodo-bi2,1,3-benzothiadiazole (3.4 g, 5 mmol), compound C2 (3.07 g, 10 mmol) and 25 mL of DMF in a three-necked flask , and stirred for 20min with nitrogen gas, then added Bu 3 N (0.907g, 10mmol) and Pd(OAc) 2 (115mg, 0.5mmol), heated to 130°C, reacted at cons...

Embodiment 3

[0114] A kind of fluorene-benzobis(benzothiadiazole) copolymer, that is, poly{fluorene-6-methyl-7-ethyl-benzo[2,1-e:3,4-e]bis( benzothiadiazole)} (n=10), denoted as copolymer P3, the structural formula is as follows:

[0115]

[0116] The preparation method comprises the following steps:

[0117] (1) Preparation of 4,9-dibromo-6-methyl-7-ethyl-benzo[2,1-e:3,4-e]bis(benzothiadiazole) (A3), method as follows:

[0118] 4,4'-dibromo-6,6'-diiodo-bi-2,1,3-benzothiadiazole was prepared according to steps (1)-(4) of step (1) of Example 1.

[0119] Compound C3, ie, 2-pentyne, having the structural formula shown in formula C3 is provided.

[0120] Add 4,4'-dibromo-6,6'-diiodo-bi2,1,3-benzothiadiazole (3.4 g, 5 mmol), compound C3 (0.68 g, 10 mmol) and 25 mL of DMF into a three-necked flask , and stirred for 20min with nitrogen gas, then added Bu 3 N (0.907g, 10mmol) and Pd(OAc) 2 (115mg, 0.5mmol), heated to 130°C, reacted at constant temperature for 4h, cooled, washed with water a...

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Abstract

The invention provides a fluorene-benzodi(benzothiadiazole) containing copolymer, a preparation method and application thereof. The fluorene-benzodi(benzothiadiazole) containing copolymer is a compound P with a general formula shown as the specification, wherein R1 and R2 are alkyl of C1-C26, R3 and R4 are H or alkyl of C8-C20, and n is an integer ranging from 10 to 84. The fluorene-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 fluorene-benzobis(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 conjugated ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C09K11/06H01L51/46H01L51/54H01L51/30
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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