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Organic conjugated small molecular material containing thianthrene end groups and preparation method thereof

A small molecule, conjugated technology, used in organic chemistry, semiconductor/solid-state device manufacturing, photovoltaic power generation, etc., can solve the problems of narrow absorption wavelength, difficult energy level regulation, high cost, and achieve high photoelectric conversion efficiency.

Active Publication Date: 2020-12-08
GUANGDONG POLYTECHNIC NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the narrow absorption wavelength of fullerene materials, the difficulty in adjusting the energy level, poor solubility, and high cost, the performance improvement and large-scale use of fullerene as electron acceptor materials for organic solar cells are severely limited.

Method used

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  • Organic conjugated small molecular material containing thianthrene end groups and preparation method thereof
  • Organic conjugated small molecular material containing thianthrene end groups and preparation method thereof
  • Organic conjugated small molecular material containing thianthrene end groups and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1: Synthesis of compound c.

[0041] Add potassium tert-butoxide to the N,N-dimethylformamide solution of compound a and compound b, and react with stirring and heating for 12 hours. Afterwards, the reaction solution was cooled to room temperature, poured into ice water containing HCl, and a precipitate was formed. The precipitated solid compound was filtered, washed with water, dried, and then separated and purified by column chromatography to obtain the target compound c. The reaction formula is:

[0042]

Embodiment 2

[0043] Example 2: Synthesis of compound d.

[0044] The compound c and acetic anhydride were sequentially added into the reaction flask, and heated to reflux for 12 hours. Afterwards, the reaction solution was cooled to room temperature, poured into ice water, and a precipitate was formed. The precipitated solid compound was filtered, washed with water, dried, and then separated and purified by column chromatography to obtain the target compound d. The reaction formula is:

[0045]

Embodiment 3

[0046] Embodiment 3: Synthesis of compound f.

[0047] Prepare a 75mL dry pressure-proof bottle, blow it with argon, add compound d, acetic anhydride (25mL) and triethylamine (15mL) into the pressure-proof bottle in turn, and add ethyl acetoacetate quickly under stirring Into the reaction liquid, after 20 minutes of ventilation, the reaction was heated to 100°C, and the reaction was carried out for 12 hours. Afterwards, the reaction solution was cooled to room temperature, poured into ice water containing HCl, a precipitate was formed, then HCl (30 mL) was added to the mixed solution, and the mixed solution was heated to reflux, reacted for 3 hours, and then the reaction was returned to room temperature , the precipitated solid compound was filtered, washed with water, dried, and then separated and purified by column chromatography, and the eluent was dichloromethane to obtain the target compound f. The reaction formula is:

[0048]

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PUM

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Abstract

The invention relates to an organic conjugated small molecular material containing thianthrene end groups and a preparation method thereof. The end group of the organic conjugated small molecular material contains thianthrene groups, and the organic conjugated small molecular material has a large conjugated area and sulfur atom substituent groups, so that intermolecular self-assembly and accumulation are facilitated, and the photovoltaic performance of the small molecular material is further improved. The invention is good in thermal stability, good in light absorption and proper in energy level, and can be dissolved in organic solvents such as chloroform, dichloromethane, tetrahydrofuran and chlorobenzene; the invention is suitable for preparing organic solar cell devices by solution processing. The material is used as an electron acceptor material, can be applied to organic solar cell devices, and can achieve a good device effect.

Description

technical field [0001] The invention relates to an organic conjugated small molecule material containing a thianthrene terminal group and a preparation method thereof, which is very suitable for use in organic solar cells. Background technique [0002] Due to the advantages of light weight, low cost, translucency, solution processing, and roll-to-roll large-area flexible devices, organic solar cells have attracted worldwide attention and are one of the hotspots in the field of new energy research. Fullerenes and their derivatives play a vital role in organic solar cell devices due to their multidimensional charge transport properties and easy formation of unique phase separation structures with donor materials. However, due to the narrow wavelength of light absorption of fullerene materials, the difficulty of adjusting the energy level, poor solubility, and high cost, the performance improvement and large-scale use of fullerene as electron acceptor materials for organic sola...

Claims

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Application Information

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IPC IPC(8): C07D495/04H01L51/42H01L51/46H01L51/44
CPCC07D495/04H10K85/113H10K85/6576H10K30/80H10K30/00Y02E10/549
Inventor 谢锐浩陈锦帆
Owner GUANGDONG POLYTECHNIC NORMAL UNIV
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