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Two-dimensional conjugated benzodifuran organic micro-molecular photovoltaic material, and preparation method and application thereof

A benzodifuran, photovoltaic material technology, applied in photovoltaic power generation, organic chemistry, semiconductor/solid-state device manufacturing, etc., to achieve the effects of good photoelectric conversion efficiency, wide absorption spectrum, and good photoelectric conversion characteristics

Active Publication Date: 2017-07-25
HUNAN UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Two-dimensional conjugated benzo[1,2-b; 3,4-b]difuran is an important electron donor unit, but after coupling it as an electron donor unit with other fused heterocyclic electron acceptor units Application in the field of organic small molecule solar cells has not been reported

Method used

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  • Two-dimensional conjugated benzodifuran organic micro-molecular photovoltaic material, and preparation method and application thereof
  • Two-dimensional conjugated benzodifuran organic micro-molecular photovoltaic material, and preparation method and application thereof
  • Two-dimensional conjugated benzodifuran organic micro-molecular photovoltaic material, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Example 1 4,8-Diisooctylthienyl-benzo(1,2-b; 4,5-b')-difuran-2,6-di(2,5-diisooctyl-3 , the preparation of 6-furyl-2-pyrrolopyrrole diketone) (M1)

[0057] Specific steps are as follows:

[0058] ①Synthesis of Compound 1

[0059] Under the protection of argon, 5 mL of anhydrous tetrahydrofuran was injected into 2-isooctylthiophene (3.92 mg, 20 mmol, purchased from Suzhou Nakai Technology Co., Ltd.), and 9.2 mL of n-butyllithium was added dropwise at 0 ° C. The system was raised to 50°C and stirred under reflux for 1.5 hours, and benzodifuran (1.5 mg, 8 mmol) was added to the reaction system. 50°C for another 1.5 hours, after cooling to room temperature, the SnCl 2 2H 2 O (14.4mg, 64mmol) was dissolved in 25.6mL of 10% hydrochloric acid solution and added dropwise to the above reaction solution. After continuing the reaction for 1.5 hours, the mixture was poured into water, extracted with dichloromethane, and the organic phase was dried over anhydrous magnesium sulfat...

Embodiment 2

[0077] Example 2 4,8-Diisooctylthienyl-benzo(1,2-b; 4,5-b')-difuran-2,6-di(2,5-diisooctyl-3 , the preparation of 6-furyl-2-pyrrolopyrrole diketone) (M1)

[0078] Specific steps are as follows:

[0079] ①Synthesis of Compound 1

[0080] Under argon protection, 5 mL of anhydrous tetrahydrofuran was injected into 2-isooctylthiophene (3.14 mg, 16 mmol, purchased from Suzhou Nakai Technology Co., Ltd.), and 9.2 mL of n-butyllithium was added dropwise at 0 ° C. The system was raised to 45°C and stirred under reflux for 1 hour, and benzodifuran (1.5 mg, 8 mmol) was added to the reaction system. 45°C for another 1 hour, after cooling to room temperature, the SnCl 2 2H 2 O (12.6mg, 56mmol) was dissolved in 25.6mL of 10% hydrochloric acid solution and added dropwise to the above reaction solution. After continuing the reaction for 1 hour, the mixture was poured into water, extracted with dichloromethane, and the organic phase was dried over anhydrous magnesium sulfate and filtered. ...

Embodiment 3

[0098] Example 3 4,8-Diisooctylthienyl-benzo(1,2-b; 4,5-b')-difuran-2,6-di(2,5-diisooctyl-3 , the preparation of 6-furyl-2-pyrrolopyrrole diketone) (M1)

[0099] Specific steps are as follows:

[0100] ①Synthesis of Compound 1

[0101] Under the protection of argon, 5 mL of anhydrous tetrahydrofuran was injected into 2-isooctylthiophene (4.70 mg, 24 mmol, purchased from Suzhou Nakai Technology Co., Ltd.), and 9.2 mL of n-butyllithium was added dropwise at 0 ° C. The system was raised to 55°C and stirred under reflux for 2 hours, and benzodifuran (1.5 mg, 8 mmol) was added to the reaction system. 55°C for another 2 hours, after cooling to room temperature, the SnCl 2 2H 2 O (16.2mg, 72mmol) was dissolved in 25.6mL of 10% hydrochloric acid solution and added dropwise to the above reaction solution. After continuing to react for 2 hours, the mixture was poured into water, extracted with dichloromethane, and the organic phase was dried over anhydrous magnesium sulfate and filt...

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Abstract

The invention discloses a two-dimensional conjugated BDF organic micro-molecular photovoltaic material, and a preparation method and an application thereof. Two-dimensional conjugated BDF organic micro-molecules with the structure represented by formula (I) are obtained by connecting a thiophene conjugate side chain-containing benzo[1,2-b;3,4-b]difuran (BDF) unit with another aryl heterocycle through a Stille coupling technology. The organic micro-molecular photovoltaic material has wide visible region absorption, suitable HOMO and LUMO energy levels and narrow band gap. Organic solar cells are produced by using the organic molecules as an electron donor and PC61BM as an electron receptor, the maximum energy conversion efficiency of the organic solar cells reaches up to 3.7%, and the organic solar cells have a good photoelectric conversion efficiency.

Description

technical field [0001] The invention relates to the technical field of photovoltaic materials, in particular to a two-dimensional conjugated benzodifuran organic small molecule photovoltaic material and its preparation method and application. Background technique [0002] Benzobiheterocyclic (benzodithiophene and benzodifuran) polymers have shown excellent performance in the field of solar cells [Bo Liu, Xuewen Chen, Yuehui He, Yongfang Li, Xinjun Xu, Lu Xiao, Lidong Li, and Yingping Zou. Journal of Materials Chemistry A, 2013, 1, 570-577; Bo Liu, Xuewen Chen, Yingping Zou, Lu Xiao, Xinjun Xu, Yuehui He, Lidong Li, and Yongfang Li. Macromolecules, 2012, 45, 6898-6905 .]. Especially the introduction of thiophene on the backbone of benzo[1,2-b; 3,4-b]dithiophene (BDT) or benzo[1,2-b; 3,4-b]difuran (BDF) After two-dimensional conjugated side chains, the photovoltaic performance has been significantly improved [Long Ye, Shaoqing Zhang, Wenchao Zhao, Huifeng Yao, and JianhuiHou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D519/00H01L51/46
CPCC07D519/00H10K85/653H10K85/655H10K85/6574H10K85/6572Y02E10/549
Inventor 刘波陈远道王晓波王钢刘骏周诗彪胡霞何敏
Owner HUNAN UNIV OF ARTS & SCI
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