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A seven-membered fused ring-like benzotriazole acceptor and its preparation method and application

A technology of benzotriazole and dinitrobenzotriazole, which is applied in the field of organic solar cell material preparation, can solve the problems of narrow optical bandgap and low photoelectric conversion efficiency, and achieve narrow optical bandgap and good production efficiency. Effect of film properties and high photoelectric conversion efficiency

Active Publication Date: 2020-03-31
CENT SOUTH UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Aiming at the problems of low photoelectric conversion efficiency of organic acceptor materials in existing organic solar cells, the first purpose of the present invention is to provide a seven-element thickener with good film-forming property, narrow optical band gap and high photoelectric conversion efficiency. Cyclic Benzotriazole Receptor Small Molecules

Method used

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  • A seven-membered fused ring-like benzotriazole acceptor and its preparation method and application
  • A seven-membered fused ring-like benzotriazole acceptor and its preparation method and application
  • A seven-membered fused ring-like benzotriazole acceptor and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] The synthetic route is expressed as follows:

[0078]

[0079]

[0080] The preparation method of BIC, its main steps are:

[0081] 1) 4,7-dibromo-2-(2-ethylhexyl)-5,6-dinitro-2H-benzo[d][1,2,3]triazole (2.5g, 5.22mmol ), tributyl(6-undecylthienothiophene)tin (6.46g, 17.3mmol) was dissolved in a flask filled with 30mL of anhydrous THF, under the protection of Ar, the gas was extracted three times, and the Pd(PPh 3 ) 2 Cl 2 (0.22g, 4mmol) was quickly added to the reaction system, and stirred under reflux at 70°C for 48h. After the reactant was cooled to room temperature, it was extracted with DCM, and the crude product was purified by a silica gel column, and the eluent was spin-dried to obtain a yellow solid (1). 1H NMR (400MHz, CDCl3) δ7.39(d, J=5.1Hz, 2H), 6.9(d, J=5.2Hz, 2H), 3.77(d, J=7.2Hz, 2H), 2.68(d, J =7.6Hz, 4H), 1.30(m, 1H), 1.50–0.90(m, 56H).

[0082] 2) Compound 1 (6.0g, 10mmol) was dissolved in a three-necked flask filled with o-dichlorobenzene...

Embodiment 2

[0095] Its main steps are with embodiment 1;

[0096] 1) Dissolve compound 3 (0.145g, 0.13mmol), 5,6-difluoro-3-(dicyanomethylene) indoketone (2FINCN) (0.27g, 1.3mmol), pyridine (1mL in a In a one-necked bottle of 30 mL of chloroform, under the protection of Ar, stirred overnight at 65 °C under reflux, cooled the reaction to room temperature, extracted with DCM, and purified the crude product with a silica gel column to obtain a dark blue solid (BFIC). (0.08 g, 40%). 1 H NMR (400MHz, CDCl 3 )δ9.34(s,1H),8.54(dd,J=5.7,2.9Hz,1H),7.76(dt,J=7.3,3.7Hz,1H),7.84–7.71(m,4H),3.90(d , J = 7.2Hz, 4H), 3.77 (d, J = 7.2Hz, 2H), 2.68 (d, J = 7.6Hz, 4H), 1.30 (m, 3H), 1.50–0.90 (m, 80H).

[0097]

[0098]

[0099] Device Fabrication and Photovoltaic Performance

[0100] Device preparation:

[0101] The donor and acceptor materials were weighed according to different ratios, and chromatographically pure chloroform was selected as the solvent. Add different additives according to th...

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Abstract

The invention discloses a seven-membered condensed ring-like benzotriazole acceptor small molecule, a preparation method and an application thereof. The compound is an n-type non-fullerene acceptor material (BIC) with a seven-membered condensed ring benzotriazole (B) with an alkyl chain as the intermediate core and a cyano group as an electron-withdrawing unit. Its preparation method is to use 4,7-dibromo-5,6-dinitrobenzotriazole compounds as raw materials, introduce thienothiophenes with alkyl chains through stille coupling reaction successively, and then carry out ring closure, through Nucleophilic substitution introduces an alkyl chain on N, introduces an aldehyde group through Vilsmeier-Haack, and finally introduces a polar conjugated unit through the Knoevenagel reaction to obtain a BIC compound. This small molecule forms a clear conformation and good solubility. Suitable electron acceptor unit, and achieve high efficiency (PCE>13%) in solar cells, it is a class of photovoltaic materials with great potential.

Description

technical field [0001] The present invention relates to an organic solar cell acceptor material, in particular to a seven-membered fused ring-like benzotriazole acceptor small molecule, and also relates to its preparation method and application in organic solar cells, belonging to organic solar cell materials Preparation technology field. Background technique [0002] With the increasingly serious energy problems, it is imminent to develop new energy sources, and solar energy has great development prospects because of its clean, non-polluting, inexhaustible and inexhaustible advantages. How to make better use of solar energy is a key solution to the energy crisis. Organic solar cells have attracted widespread attention from researchers because of their flexibility and low cost, which can be prepared at low cost. After more than 20 years of development, the current efficiency of single-layer heterojunction organic solar cells has reached 14%, and it is likely to replace tra...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/22H01L51/42H01L51/46
CPCC07D495/22H10K85/657H10K30/00Y02E10/549
Inventor 邹应萍罗妹袁俊周流洋蔡方方江文辉
Owner CENT SOUTH UNIV
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