Benzothiadiazole unit-based A-pi-A'-pi-A type acceptor photovoltaic material, and preparation method and application thereof

A technology of benzothiadiazole and photovoltaic materials, which is applied in the fields of organic semiconductor device materials, photovoltaic power generation, semiconductor/solid-state device manufacturing, etc., can solve the problems of long synthesis steps and lack of systematic research on the photovoltaic performance of materials, and achieve the goal of synthesis Fewer steps, improved planarity, and high yield

Active Publication Date: 2018-02-02
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, most of the A-A′-A acceptor materials based on benzothiadiazole units reported in the literature have fewer types, longer synthesis steps, and lack of systematic research on the photovoltaic properties of materials with different electron-withdrawing terminal substituents.

Method used

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  • Benzothiadiazole unit-based A-pi-A'-pi-A type acceptor photovoltaic material, and preparation method and application thereof
  • Benzothiadiazole unit-based A-pi-A'-pi-A type acceptor photovoltaic material, and preparation method and application thereof
  • Benzothiadiazole unit-based A-pi-A'-pi-A type acceptor photovoltaic material, and preparation method and application thereof

Examples

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Embodiment 1

[0054] This example discloses the specific synthesis process of the organic small molecule donor material M1, the steps are as follows:

[0055] Under nitrogen protection, compound A' (0.25 mmol, 0.171 g), compound A1 (0.58 mmol, 0.214 g), tetrakis(triphenylphosphine) palladium (0.025 mmol, 29 mg) and potassium carbonate (10 mmol, 1.380 g ) in a 50 mL three-neck flask, 10 mL of toluene, 5 mL of ethanol, and 5 mL of water were added in sequence, and heated at reflux at 110 °C for 48 h. The reaction solution was cooled to room temperature, poured into 20 mL of water and extracted with dichloromethane (3 × 30 mL), the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The crude product was extracted with petroleum ether at a volume ratio of 3:1 / dichloromethane as developing solvent for column chromatography and recrystallization with petroleum ether / ethanol to obtain 0.183 g of black powder with a yield of 71.8%...

Embodiment 2

[0062] This example discloses the specific synthesis process of the organic small molecule donor material M2, including the following steps:

[0063] Under nitrogen protection, compound A' (0.25 mmol, 0.171 g), compound A2 (0.58 mmol, 0.214 g), tetrakis(triphenylphosphine) palladium (0.025 mmol, 29 mg) and potassium carbonate (10 mmol, 1.380 g ) in a 50 mL three-neck flask, 10 mL of toluene, 5 mL of ethanol, and 5 mL of water were added in sequence, and heated at reflux at 110 °C for 48 h. The reaction solution was cooled to room temperature, poured into 20 mL of water and extracted with dichloromethane (3 × 30 mL), the organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The volume ratio of the crude product was 3:2 to 1: 1 petroleum ether / dichloromethane was used as developing solvent for column chromatography gradient separation and recrystallization with petroleum ether / dichloromethane / ethanol to obtain 0.23...

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Abstract

The invention discloses a benzothiadiazole unit-based A-pi-A'-pi-A type acceptor photovoltaic material, and a preparation method and an application thereof, and belongs to the field of organic photoelectric materials. The material adopts benzothiadiazole as a nucleus, adopts a nitro group and a 4-fluorophenyl group as end groups, and adopts a 2-cyano-styryl group as a pi connecting bond; and alkyl-modified thienyl groups are introduced to two sides of the benzothiadiazole unit in order to improve the solubility of the material, extend the conjugation length of a molecule and enhance the intramolecular charge transfer ability. The organic small molecular material obtains Jsc exceeding 1.0 mA cm<-2>, and has large redshifts being 34 nm and 38 nm respectively. The PCE of the material is increased from 0.1% to 1.0% and increases 10 times after replacing the nitro end group (M1) with the 4-fluorophenyl group (M2) due to the M2 having high Jsc and Voc, so the M2 material has higher potentialto be a high-efficiency non-fullerene small molecular acceptor photovoltaic material than the M1.

Description

technical field [0001] The invention relates to an A-π-A′-π-A type non-fullerene organic small molecule acceptor photovoltaic material based on a benzothiadiazole unit and a preparation method thereof, and the material is used as a non-fullerene small The molecular acceptor material is made into a bulk heterojunction photovoltaic device, which belongs to the field of organic photovoltaic materials. Background technique [0002] At present, commercialized fullerene derivatives (including PC 61 BM, PC 71 BM) due to some disadvantages, such as expensive, difficult preparation and purification, narrow light absorption range (<600 nm), weak absorption capacity, etc. In contrast, non-fullerene organic small molecule acceptors have a wider absorption range, are simple to prepare, and are easy to obtain higher V oc Etc. Therefore, since 2014, researchers have gradually turned their attention to the development of different types of new non-fuller acceptor photovoltaic materi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14H01L51/42H01L51/46
CPCC07D417/14H10K85/655H10K85/657H10K30/00H10K2102/00Y02E10/549
Inventor 谢宝殷伦祥李艳芹
Owner DALIAN UNIV OF TECH
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