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

A technology of benzothiadiazole and triphenylamine, which is applied in the field of triphenylamine-benzodipolymer and its preparation and application, can solve the problems of low energy conversion efficiency, achieve reduced preparation costs, good electron transport properties, Effect of improving solubility and film-forming properties

Inactive Publication Date: 2014-05-07
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 triphenylamine 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 to improve optoelectronic The energy conversion efficiency of materials is important for the development of organic solar cells

Method used

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

Examples

Experimental program
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Effect test

Embodiment 1

[0065] A triphenylamine-benzobis(benzothiadiazole) copolymer, namely poly{triphenylamine-6,7-bis(3,7-dimethyl)octyl-benzo[2,1-e3 ,4-e] bis(benzothiadiazole)} (n=55), denoted as copolymer P1:

[0066]

[0067] The preparation method comprises the following steps:

[0068] 1. Preparation of 4,4'-bis((4,4,5,5-tetramethyl-1,3,2-dioxaborolane)triphenylamine (A1), including the following steps:

[0069] Provide compound C1, namely 4,4'-dibromotriphenylamine;

[0070] Under the protection of nitrogen, compound C1 (12.10g, 0.03mol) and 200mL tetrahydrofuran were added to the three-necked flask, and the n-hexane solution (25.2mL, 2.5M , 0.06mol), continue to stir the reaction for 2h, then add 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (13mL, 0.06mol), Stir overnight at room temperature, add the reaction solution after the reaction to 60 mL of saturated aqueous sodium chloride solution to terminate the reaction, extract with anhydrous ether, dry over anhydrous sodium sul...

Embodiment 2

[0097] A triphenylamine-benzobis(benzothiadiazole) copolymer, poly{4”-decyltriphenylamine-6-(3,7-dimethyl)octyl-7-n-eicosyl -Benzo[2,1-e:3,4-e]bis(benzothiadiazole)} (n=80), denoted as copolymer P2:

[0098]

[0099] The preparation method comprises the following steps:

[0100] 1. The preparation method of 4"-decyl-4,4'-di((4,4,5,5-tetramethyl-1,3,2-dioxaborolane) triphenylamine (A2) includes The following steps:

[0101] Provide compound C2, namely 4"-decyl-4,4'-dibromotriphenylamine;

[0102] Under the protection of nitrogen, compound C2 (5.43g, 0.01mol) and 80mL tetrahydrofuran were added to the three-necked flask, and the n-hexane solution (8.4mL, 2.5M , 0.02mol), continue to stir the reaction for 2h, then add 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.3mL, 0.02mol) , stirred at room temperature overnight, the reaction solution after the reaction was added into 60mL saturated aqueous sodium chloride solution to terminate the reaction, extracted with an...

Embodiment 3

[0118] A triphenylamine-benzobis(benzothiadiazole) copolymer, namely poly{4”-octyloxytriphenylamine-6,7-bis(3,7-dimethyl)octyl-benzo [2,1-e:3,4-e]bis(benzothiadiazole)} (n=65), denoted as copolymer P3:

[0119]

[0120] The preparation method comprises the following steps:

[0121] 1. Preparation method of 4"-octyloxy-4,4'-bis((4,4,5,5-tetramethyl-1,3,2-dioxaborolane)triphenylamine (A3) Include the following steps:

[0122] Provide compound C3, namely 4"-octyloxy-4,4'-dibromotriphenylamine;

[0123] Under the protection of nitrogen, compound C3 (5.31g, 0.01mol) and 80mL tetrahydrofuran were added to the three-necked flask, and the n-hexane solution (8.4mL, 2.5M , 0.02mol), continue to stir the reaction for 2h, then add 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.3mL, 0.02mol) , stirred at room temperature overnight, the reaction solution after the reaction was added into 60mL saturated aqueous sodium chloride solution to terminate the reaction, extracted wit...

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Abstract

The invention provides a triphenylamine-benzodi(benzothiadiazole) containing copolymer, preparation and application thereof. The triphenylamine-benzodi(benzothiadiazole) containing copolymer is a compound P with a structural formula shown as the specification, wherein R1 and R2 are alkyl of C1-C20, R3 is H, alkyl of C1-C20 or alkoxy of C8, and n is an integer ranging from 1 to 100. The triphenylamine-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 triphenylamine-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 limited sources of inorganic semiconductor materials, silicon solar cells that have been commercialized at present are expensive, toxic, complex preparation process and high cost, and their applications are 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G61/12C07D513/04H01L51/46H01L51/54
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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