A kind of 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., can solve problems such as few reports, and achieve wide absorption spectrum, good processability, and good photoelectric conversion characteristics. Effect

Active Publication Date: 2019-05-24
HUNAN UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Benzo[1,2-b; 3,4-b]difuran (BDF) has been well used as an electron donor in polymer solar cells, and it is a class of electron donor units with excellent performance [Bo Liu,Xuewen Chen,Yingping Zou,LuXiao,Xinjun Xu,Yuehui He,Lidong Li,and Yongfang Li.Macromolecules,2012,45,6896-6905.], but coupled with other electron acceptor units as electron donor Later applications in the field of small organic molecule solar cells are rarely reported in the literature

Method used

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  • A kind of benzodifuran organic small molecule photovoltaic material and its preparation method and application
  • A kind of benzodifuran organic small molecule photovoltaic material and its preparation method and application
  • A kind of benzodifuran organic small molecule photovoltaic material and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1 4,8-Diisooctyloxy-benzo(1,2-b; 4,5-b')-difuran-2,6-bis(2,5-Diisooctyl-3, Preparation of 6-furyl-2-diketopyrrolopyrrole) (M1)

[0055] Specific steps are as follows:

[0056] ①Synthesis of Compound 1

[0057] Mix benzodifuran-4,8-dione (1.88g, 10mmol), NaOH (6.0g, 150mmol) and zinc powder (1.43g, 22mmol) in 30mL of water, stir and reflux for 1 hour, add bromo Isooctane (3.86g, 20mmol) was refluxed for 2 hours, then zinc powder (0.2g, 3mmol) was added, and the reaction was continued overnight. Cool to room temperature, pour the mixture into water, extract with dichloromethane, wash the organic phase twice with water, dry over anhydrous magnesium sulfate, spin to dry the solvent, and pass the crude product through a silica gel column (petroleum ether is the eluent) to obtain a colorless oily liquid Compound 1 (2.19 g, yield 53%).

[0058] The NMR spectrum, mass spectrum and elemental analysis of compound 1 are as follows:

[0059] 1 H NMR (400MHz, CDCl 3 ,...

Embodiment 2

[0075] Example 2 4,8-Diisooctyloxy-benzo(1,2-b; 4,5-b')-difuran-2,6-bis(2,5-Diisooctyl-3, Preparation of 6-furyl-2-diketopyrrolopyrrole) (M1)

[0076] Specific steps are as follows:

[0077] ①Synthesis of Compound 1

[0078] Mix benzodifuran-4,8-dione (1.88g, 10mmol), NaOH (6.0g, 150mmol) and zinc powder (1.43g, 22mmol) in 30mL of water, stir and reflux for 1 hour, add bromo Isooctane (4.83g, 25mmol) was refluxed for 2 hours, then zinc powder (0.2g, 3mmol) was added, and the reaction was continued overnight. Cool to room temperature, pour the mixture into water, extract with dichloromethane, wash the organic phase twice with water, dry over anhydrous magnesium sulfate, spin to dry the solvent, and pass the crude product through a silica gel column (petroleum ether is the eluent) to obtain a colorless oily liquid Compound 1 (1.95 g, yield 47%).

[0079] The NMR spectrum, mass spectrum and elemental analysis of compound 1 are as follows:

[0080] 1 H NMR (400MHz, CDCl 3 ,...

Embodiment 3

[0096] Example 3 4,8-Diisooctyloxy-benzo(1,2-b; 4,5-b')-difuran-2,6-di(2,5-diisooctyl-3, Preparation of 6-furyl-2-diketopyrrolopyrrole) (M1)

[0097] ①Synthesis of Compound 1

[0098] Mix benzodifuran-4,8-dione (1.88g, 10mmol), NaOH (6.0g, 150mmol) and zinc powder (1.43g, 22mmol) in 30mL of water, stir and reflux for 1 hour, add bromo Isooctane (5.79g, 30mmol) was refluxed for 2 hours, and zinc powder (0.2g, 3mmol) was added, and the reaction was continued overnight. Cool to room temperature, pour the mixture into water, extract with dichloromethane, wash the organic phase twice with water, dry over anhydrous magnesium sulfate, spin to dry the solvent, and pass the crude product through a silica gel column (petroleum ether is the eluent) to obtain a colorless oily liquid Compound 1 (2.10 g, yield 51%).

[0099] The NMR spectrum, mass spectrum and elemental analysis of compound 1 are as follows:

[0100] 1 H NMR (400MHz, CDCl 3 ,ppm):7.87(m,2H),7.37(m,2H),4.72(t,4H),2.12(...

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Abstract

The invention discloses a benzodifuran organic small molecular photovoltaic material, a preparation method and application thereof. The present invention synthesizes a benzo[1,2-b; 3,4-b]difuran (BDF) organic electron donor unit containing different alkoxy side chains, and the BDF unit is synthesized by a method of Stille coupling The BDF organic small molecule photovoltaic material is obtained by connecting another electron acceptor unit diketopyrrolopyrrole (DPP) through a carbon-carbon single bond, and the structure 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 or organic matter electron acceptor is used as electron acceptor to prepare organic solar cells, and its highest energy conversion efficiency can reach 5.0%, which has good photoelectric conversion efficiency.

Description

technical field [0001] The invention relates to the technical field of photovoltaic materials, in particular to a benzodifuran organic small molecule photovoltaic material and its preparation method and application. Background technique [0002] Benzo[1,2-b; 3,4-b]difuran (BDF) has been well used as an electron donor in polymer solar cells, and it is a class of electron donor units with excellent performance [Bo Liu,Xuewen Chen,Yingping Zou,LuXiao,Xinjun Xu,Yuehui He,Lidong Li,and Yongfang Li.Macromolecules,2012,45,6896-6905.], but coupled with other electron acceptor units as electron donor Later applications in the field of small organic molecule solar cells are rarely reported in the literature. BDF has a condensed heterocyclic structure similar to that of benzo[1,2-b; 3,4-b]dithiophene (BDT), and BDT is used as an electron donor in organic small molecule solar cells, obtaining up to 5.8% Energy conversion efficiency [Yuze Lin, Lanchao Ma, Yongfang Li, Yunqi Liu, Daoben...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00H01L51/46
CPCC07D519/00H10K85/653H10K85/6574H10K85/6572Y02E10/549
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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