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Heptatomic condensed ring benzotriazole receptor and preparation method and application thereof

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 manufacturing efficiency. Membrane, good solubility effect

Active Publication Date: 2018-12-07
CENT SOUTH UNIV
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  • Summary
  • 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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  • Heptatomic condensed ring benzotriazole receptor and preparation method and application thereof
  • Heptatomic condensed ring benzotriazole receptor and preparation method and application thereof
  • Heptatomic condensed ring benzotriazole receptor and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] The synthetic route is expressed as follows:

[0078]

[0079] The preparation method of BIC, its main steps are:

[0080] 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).

[0081] 2) Compound 1 (6.0g, 10mmol) was dissolved in a three-necked flask filled with o-dichlorobenzene (o-DCB, 100...

Embodiment 2

[0094] Its main steps are with embodiment 1;

[0095] 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, reflux and stir overnight at 65° C., the reaction was cooled to room temperature, extracted with DCM, and the crude product was purified 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).

[0096]

[0097] Device Fabrication and Photovoltaic Performance

[0098] Device preparation:

[0099] 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 the needs....

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Abstract

The invention discloses a heptatomic condensed ring benzotriazole receptor micromolecule and a preparation method and application thereof. The compound takes heptatomic condensed ring benzotriazole (B) with an alkyl chain as intercalated nucleus, and cyan group as n-type fullerene receptor material (BIC) of an electrophilic unit. The preparation method comprises the following steps: by taking 4,7-dibromo-5,6-dinitro benzotriazole compound as a raw material, sequentially introducing thienothiophene with an alkyl chain by stille coupling reaction, then performing loop closing, introducing the alkyl chain to N by nucleophilic substitution, introducing aldehyde group via Vilsmeier-Haack, and then introducing a polar conjugation unit by Knoevenage reaction, so as to obtain a BIC compound; the micromolecule forms definite conformation and good solubility, has an electron receptor unit with universality, obtains a high efficiency (PCE of 13%) on a solar cell, and thus is a photovoltaic material full of 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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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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