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Compound with nitro-based electron withdrawing group, non-fullerene electron acceptor material and preparation method of non-fullerene electron acceptor material

A technology of electron acceptor materials and electron-withdrawing groups, which is applied in the field of organic solar cells, can solve problems such as unfavorable industrial production, operator injury, and easy pollution of the environment, so as to improve fill factor and short-circuit current, improve utilization rate, The effect of improving transmission performance

Active Publication Date: 2020-09-08
YANGTZE NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This type of compound itself may be toxic, and the highly toxic malononitrile must be used in the synthesis process, so it is easy to cause harm to operators during the preparation process, which is not conducive to actual industrial production, and is easy to pollute the environment

Method used

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  • Compound with nitro-based electron withdrawing group, non-fullerene electron acceptor material and preparation method of non-fullerene electron acceptor material
  • Compound with nitro-based electron withdrawing group, non-fullerene electron acceptor material and preparation method of non-fullerene electron acceptor material
  • Compound with nitro-based electron withdrawing group, non-fullerene electron acceptor material and preparation method of non-fullerene electron acceptor material

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045]A method for preparing a compound with a nitro-based electron-withdrawing group, comprising the steps of:

[0046] S1. Add 1H-indene-1,3(2H)-dione (10.0mmol) and dichloromethanesulfonyl chloride (11.0mmol) to tetrahydrofuran (100ml) solvent containing triethylamine (20.0mmol), at room temperature After stirring for 2 h, it was extracted with dichloromethane and the solvent was removed. The organic phase was dried with anhydrous sodium sulfate, and the obtained organic layer was purified by column chromatography to obtain intermediate product C1 (3.5 g, yield 64.0%), wherein ethyl acetate:methanol (3:1) was used as eluent. The intermediate product C1 is identified and analyzed by a mass spectrometer, and the result is: mass spectrum (EI): m / z C 16 h 22 C l3 NO 4 Theoretical value of S: 429.03; measured value: 430(M)+.

[0047] S2. Add C1 (10.0mmol) into a round bottom flask containing MeOH (30ml) and NH4OH (30.0mmol), stir for 6h, extract the obtained product with et...

Embodiment 2

[0051] A preparation method of a non-fullerene electron acceptor material, mainly formed by the Knoevenagel reaction of the compound EG1 and the compound T having an electron-withdrawing group based on a nitro group; the specific reaction steps are as follows:

[0052] S11. Add compound T and compound EG1 to a mixed solution of pyridine and chloroform for dissolution, then react at 65°C under nitrogen protection and reflux for 24 hours, cool to room temperature, introduce the mixture into methanol and filter;

[0053] S12. Purify the filtered residue by silica gel column chromatography, using dichloromethane:petroleum ether (1:1) as the eluent to obtain a solid product, that is, the non-fullerene electron acceptor material.

Embodiment 3

[0055] The electron-withdrawing group (EG1) prepared in Example 1 and the structural formula are The target compound T1, prepared by Knoevenagel reaction structural formula is The non-fullerene electron acceptor material T2.

[0056] Specific steps are as follows:

[0057] S11, compound T1 (0.15g, 0.15mmol), compound EG1 (0.20g, 0.85mmol), pyridine (1mL) and chloroform (45mL) were mixed and dissolved in a round bottom flask under nitrogen, and the mixed solution was heated at 65°C The reaction was stirred under the conditions for 24h. Then allowed to cool to room temperature, the mixture was introduced into methanol and filtered.

[0058] S12. Purify the residue by silica gel column chromatography, using dichloromethane:petroleum ether (1:1) as the eluent, and finally obtain the solid product non-fullerene electron acceptor material T2 (0.14g, yield 40%) .

[0059] The non-fullerene electron acceptor material T2 is identified and analyzed by a mass spectrometer, and the...

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Abstract

The invention discloses a compound with a nitro-based electron withdrawing group, a non-fullerene electron acceptor material and a preparation method of the non-fullerene electron acceptor material, wherein the compound with the nitro-based electron withdrawing group has the following structure defined in the specification, and R1 and R2 are H, F, Cl, Br, I or -CH3. According to the invention, themain functional group in the compound with the nitro-based electron withdrawing group provided by the invention is nitro and does not contain cyano (-C[triplebond]N), so that the compound has the advantage of environmental friendliness; and the non-fullerene electron acceptor material prepared from the compound has low LUMO energy level and strong electron affinity compared with the existing non-fullerene electron acceptor material, and is beneficial to enhancing the electron withdrawing capacity, enhancing the utilization ratio of solar energy and enhancing the transmission performance of electrons.

Description

technical field [0001] The invention relates to the technical field of organic solar cells, in particular to a compound with a nitro-based electron-withdrawing group, a non-fullerene electron acceptor material and a preparation method thereof. Background technique [0002] An organic solar cell is a solar cell whose core part is composed of organic materials. It mainly uses organic substances with photosensitive properties as semiconductor materials, and generates voltage to form current through photovoltaic effect. An organic solar cell is a sandwich-type electronic device based on a bulk heterojunction structure. The active layer in the middle is the main component to realize photoelectric conversion. It is a blend of n-type electron transport materials and p-type hole transport materials. Composition, the traditional n-type materials are fullerene materials, due to the poor absorption of fullerene materials in the visible light range, the structure is not easy to adjust, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C205/45C07C201/12C07D495/22C07D495/04C07D513/22C07D517/22H01L51/42H01L51/46
CPCC07C205/45C07D495/22C07D495/04C07D513/22C07D517/22C07C2602/08H10K85/615H10K85/626H10K85/6576H10K85/657H10K30/30Y02E10/549
Inventor 姚闯杨叶子
Owner YANGTZE NORMAL UNIVERSITY
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