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A kind of a-π-a'-π-a type acceptor photovoltaic material based on benzothiadiazole unit and its preparation method and application

A benzothiadiazole and photovoltaic material technology, which is applied in the fields of organic semiconductor device materials, photovoltaic power generation, semiconductor/solid-state device manufacturing, etc. Fewer steps, improved planarity, and high yield

Active Publication Date: 2020-11-10
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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  • A kind of a-π-a'-π-a type acceptor photovoltaic material based on benzothiadiazole unit and its preparation method and application
  • A kind of a-π-a'-π-a type acceptor photovoltaic material based on benzothiadiazole unit and its preparation method and application
  • A kind of a-π-a'-π-a type acceptor photovoltaic material based on benzothiadiazole unit and its preparation method and application

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Experimental program
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Effect test

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' (0.25mmol, 0.171g), compound A1 (0.58mmol, 0.214g), tetrakis (triphenylphosphine) palladium (0.025mmol, 29mg) and potassium carbonate (10mmol, 1.380g) were placed Into a 50mL three-neck flask, add 10mL toluene, 5mL ethanol and 5mL water successively, and heat at reflux at 110°C for 48h. 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. Chloromethane was used as developing solvent for column chromatography separation and recrystallization with petroleum ether / ethanol to obtain 0.183 g of black powder with a yield of 71.8%.

[0056] The reaction scheme of preparing above-mentioned compound M1 is as fo...

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' (0.25mmol, 0.171g), compound A2 (0.58mmol, 0.214g), tetrakis (triphenylphosphine) palladium (0.025mmol, 29mg) and potassium carbonate (10mmol, 1.380g) were placed Into a 50mL three-neck flask, add 10mL toluene, 5mL ethanol and 5mL water successively, and heat at reflux at 110°C for 48h. 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. Petroleum ether / dichloromethane was used as a developing solvent for column chromatography gradient separation and recrystallization with petroleum ether / dichloromethane / ethanol to obtain 0.230 g of a red solid with a yield of 82.1%.

[0064] The reaction scheme ...

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Abstract

An A-π-A'-π-A type acceptor photovoltaic material based on a benzothiadiazole unit and a preparation method and application thereof belong to the field of organic photoelectric materials. The material uses benzothiadiazole as the core, nitro and 4-fluorophenyl as the terminal group, and 2-cyano-styryl as the π linkage; introduce alkyl-modified The thiophene group can improve the solubility of the material, extend the conjugation length of the molecule, and enhance the charge transport ability within the molecule. These organic small molecule materials obtained more than 1.0 mA cm ‑2 of J sc , both produce large red shifts, which are 34 nm and 38 nm, respectively. Among them, by replacing the nitro end group (M1) with 4-fluorophenyl (M2), the PCE of the material increased from 0.1% to 1.0%, which was a 10-fold increase, which was mainly due to the high J sc and V oc , indicating that the M2 material has the potential to become a high-efficiency non-fullerene small molecule acceptor photovoltaic material compared with 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) has some disadvantages, such as expensive, difficult preparation and purification, narrow light absorption range (<600nm), 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 through energy level adjustment. oc Etc. Therefore, since 2014, researchers have gradually turned their attention to the development of different types of new non-fuller ...

Claims

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Application Information

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Patent Type & Authority Patents(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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