A kind of two-dimensional conjugated benzodifuran organic small molecule photovoltaic material and its preparation method and application

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

Active Publication Date: 2019-04-12
HUNAN UNIV OF ARTS & SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • A kind of two-dimensional conjugated benzodifuran organic small molecule photovoltaic material and its preparation method and application
  • A kind of two-dimensional conjugated benzodifuran organic small molecule photovoltaic material and its preparation method and application
  • A kind of two-dimensional conjugated benzodifuran organic small molecule photovoltaic material and its preparation method and application

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-bis(2,5-diisooctyl-3 Preparation of ,6-furyl-2-pyrrolopyrrole dione)(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.), 9.2 mL of n-butyllithium was added dropwise at 0 °C, and The system was raised to 50°C and the reaction was refluxed and stirred for 1.5 hours, and benzodifuran (1.5 mg, 8 mmol) was added to the reaction system. The reaction was carried out at 50°C for another 1.5 hours, and after cooling to room temperature, the SnCl 2 ·2H 2 O (14.4 mg, 64 mmol) was dissolved in 25.6 mL 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 and extracted with dichloromethane. The organic ...

Embodiment 2

[0077] Example 2 4,8-Diisooctylthienyl-benzo(1,2-b; 4,5-b')-difuran-2,6-bis(2,5-diisooctyl-3 Preparation of ,6-furyl-2-pyrrolopyrrole dione)(M1)

[0078] Specific steps are as follows:

[0079] ①Synthesis of compound 1

[0080] Under the protection of argon, 5 mL of anhydrous tetrahydrofuran was injected into 2-isooctylthiophene (3.14 mg, 16 mmol, purchased from Suzhou Nakai Technology Co., Ltd.), 9.2 mL of n-butyllithium was added dropwise at 0 °C, and The system was raised to 45°C and the reaction was refluxed and stirred for 1 hour, and benzodifuran (1.5 mg, 8 mmol) was added to the reaction system. React at 45°C for another 1 hour, and after cooling to room temperature, the SnCl 2 ·2H 2 O (12.6 mg, 56 mmol) was dissolved in 25.6 mL 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 ...

Embodiment 3

[0098] Example 3 4,8-Diisooctylthienyl-benzo(1,2-b; 4,5-b')-difuran-2,6-bis(2,5-diisooctyl-3 Preparation of ,6-furyl-2-pyrrolopyrrole dione)(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.), 9.2 mL of n-butyllithium was added dropwise at 0 °C, and The system was raised to 55°C and the reaction was refluxed and stirred for 2 hours, and benzodifuran (1.5 mg, 8 mmol) was added to the reaction system. The reaction was carried out at 55°C for another 2 hours, and after cooling to room temperature, the SnCl 2 ·2H 2 O (16.2 mg, 72 mmol) was dissolved in 25.6 mL of 10% hydrochloric acid solution and added dropwise to the above reaction solution. After continuing the reaction for 2 hours, the mixture was poured into water, extracted with dichloromethane, and the organic phase...

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Abstract

The invention discloses a two-dimensional conjugated BDF organic small molecule photovoltaic material, a preparation method and an application thereof. In the present invention, the benzo[1,2-b; 3,4-b]difuran (BDF) unit containing the thiophene conjugated side chain is combined with another BDF unit through a carbon-carbon single bond through a Stille coupling method. An aromatic heterocycle is connected to obtain a two-dimensional conjugated BDF-like organic small molecule, the structure of which is shown in formula (I). These organic small molecule photovoltaic materials have wide absorption in the visible region, suitable HOMO and LUMO energy levels and relatively narrow bandgap. Using such organic molecules as electron donors, PC 61 BM has prepared organic solar cells for electron acceptors, and its highest energy conversion efficiency can reach 3.7%, which has 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-based organic small molecule photovoltaic material and a preparation method and application thereof. Background technique [0002] Benzodiheterocycle (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 .]. In particular, the introduction of thiophenes 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 is significantly improved [Long Ye, Shaoqing Zhang, Wenchao Zhao, Huifeng Yao, and Jianhui ...

Claims

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Application Information

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Patent Type & Authority Patents(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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