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A-pi-D-pi-A type BODIPY small molecular photovoltaic material and preparation method and application thereof

A small molecule compound, selected technology, applied in photovoltaic power generation, chemical instruments and methods, semiconductor/solid-state device manufacturing, etc., can solve the problems of lack of π bridge system research, few types of BODIPY conjugated small molecules, and low device efficiency.

Active Publication Date: 2020-10-23
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] So far, there are few types of BODIPY conjugated small molecules based on A-π-D-π-A type, and the device efficiency is generally low, and this kind of backbone molecules are mainly constructed by Suzuki coupling reaction (or Sonogashira coupling reaction)
In addition, there is a lack of systematic studies on the π bridge in A-π-D-π-A type BODIPY conjugated small molecules

Method used

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  • A-pi-D-pi-A type BODIPY small molecular photovoltaic material and preparation method and application thereof
  • A-pi-D-pi-A type BODIPY small molecular photovoltaic material and preparation method and application thereof
  • A-pi-D-pi-A type BODIPY small molecular photovoltaic material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0092] This example discloses the synthesis of compound Q1, the specific synthesis steps are as follows:

[0093] Under nitrogen, the compound ABr (0.720g, 1.52mmol), tetrakis (triphenylphosphine) palladium (26mg, 0.023mmol) was dissolved in 15mL of toluene, and then containing 9-octyl-2,7-bis{ A solution of 5-(tributyltinyl)-thiophen-2-yl}carbazole (0.409g, 0.40mmol) in 15mL of toluene was injected into the reaction system and refluxed at 110°C for 48h. The end of the reaction was detected by TLC, and the solvent in the reaction solution was removed. The crude product was separated by column chromatography with a mixture of petroleum ether / dichloromethane (2:1 by volume), and finally 0.168 g of a dark green solid was obtained, with a yield of 34%.

[0094] The reaction formula of preparing above-mentioned compound Q1 is as follows:

[0095]

[0096] see figure 1 , is the normalized UV-Vis spectrum absorption figure of compound Q1 in chloroform solution and film-forming st...

Embodiment 2

[0100] This embodiment discloses the synthesis of compound Q2, and the specific synthesis steps are as follows:

[0101] Under nitrogen, the compound ABr (0.948g, 2.00mmol), tetrakis (triphenylphosphine) palladium (46mg, 0.04mmol) was dissolved in 20mL of toluene, and then containing 5,11-dioctyl-2,8 - Inject 20 mL of toluene solution of bis{5-(tributyltin)-thiophen-2-yl}indole[3,2-b]carbazole (0.819g, 0.67mmol) into the reaction system, and reflux at 110°C for 48h . The end of the reaction was detected by TLC, and the solvent in the reaction solution was removed. The crude product was separated by column chromatography with a mixture of petroleum ether / dichloromethane (1:1 by volume), and finally 0.144 g of a dark green solid was obtained, with a yield of 15%.

[0102] The reaction formula of preparing above-mentioned compound Q2 is as follows:

[0103]

[0104] see Figure 4 , is the normalized UV-Vis spectrum absorption figure of compound Q2 in chloroform solution and...

Embodiment 3

[0108] This example discloses the synthesis of compound Q3, the specific synthesis steps are as follows:

[0109] Under nitrogen, the compound ABr (1.896g, 4.00mmol), tetrakis (triphenylphosphine) palladium (46mg, 0.040mmol) was dissolved in 20mL of toluene, and then containing 9,9-dioctyl-2,7 - A 20 mL toluene solution of bis{5-(tributyltin-yl)-thiophen-2-yl}fluorene (1.812 g, 1.60 mmol) was injected into the reaction system, and refluxed at 110° C. for 48 h. The end of the reaction was detected by TLC, and the solvent in the reaction solution was removed. The crude product was separated by column chromatography with a mixture of petroleum ether / dichloromethane (1:2 by volume), and finally 0.150 g of a dark green solid was obtained, with a yield of 7%.

[0110] The reaction formula of preparing above-mentioned compound Q3 is as follows:

[0111]

[0112] see Figure 7 , is the normalized UV-Vis spectrum absorption figure of compound Q3 in chloroform solution and film-for...

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Abstract

The invention discloses an A-pi-D-pi-A type BODIPY small molecular photovoltaic material and a preparation method and application thereof, and belongs to the technical field of organic synthesis. According to the compound, carbazole, fluorene, indolocarbazole, phenothiazine, triphenylamine, benzodithiophene, indacenedithiophene, dithienopyrrole, cyclopentadithiophene and the like are used as electron donating units (D), and X-group and Y-group substituted BODIPY units (A) are bridged through different numbers of thiophene (pi) respectively. HOMO energy levels and band gaps of molecules are cooperatively regulated and controlled by utilizing different numbers of D units and pi bridges, so that the photoelectric conversion efficiency of the material is improved. The compound has the potential of becoming a high-efficiency and high-current organic small-molecule photovoltaic material, and broadens the research thought for developing BODIPY photovoltaic materials with different molecular skeletons.

Description

technical field [0001] The invention belongs to the field of organic photovoltaic technology, and specifically relates to a class of A-π- D-π-A type small molecule and its preparation method, and the application of this type of molecule as p-type material in the photoactive layer in the field of organic solar cells. Background technique [0002] Energy has always been an important factor in promoting economic and social development, and solar energy is regarded as one of the effective solutions to the current energy crisis. Due to the advantages of light weight, low cost, solution processing, bendability, and large-area preparation, the research of organic solar cells (including p-type and n-type material design, device engineering, etc.) has become an important research content for researchers. Compared with polymer materials, organic small molecules have a clear molecular structure, are easy to synthesize repeatedly in batches, and are relatively simple to separate and pu...

Claims

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Application Information

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IPC IPC(8): C07F5/02H01L51/42H01L51/46
CPCC07F5/022H10K85/60H10K85/615H10K85/655H10K85/6572H10K85/322H10K30/30Y02E10/549
Inventor 谢宝李艳芹殷伦祥
Owner DALIAN UNIV OF TECH
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