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Tetracyano-anthraquinone dimethane micromolecular receptor material as well as preparation method and application thereof

A technology of tetracyanoanthraquinone dimethane and small molecules, which is applied in the direction of luminescent materials, carboxylic acid nitrile preparation, chemical instruments and methods, etc. It can solve the problems of poor solubility of compounds, application limitations, and low charge carrier mobility. , to achieve the effects of good matching, good solubility, and improved electron transport performance

Active Publication Date: 2020-05-01
HENAN CHEM IND RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Through the efforts of scientific researchers, in just two decades, its photoelectric conversion efficiency has increased from 10 -2 -10 -3 % increased to 17.3% [L. Meng, Y. Zhang, X. Wan, et al. Science, 10.1126 / science.aat2612 (2018)], but compared with the conversion efficiency of inorganic solar cells, there is still a certain gap, An important factor limiting the energy conversion efficiency of organic solar cells is the low charge carrier mobility of currently used organic solar cell materials [Markus C. Scharber, David Muhlbacher, Markus Koppe, et al. ]
[0003] Tetracyanoanthraquinone dimethane has good photochemical and photophysical stability and strong electron affinity. Since 1985, it has been studied as an acceptor material [Kini, A.M., et al., Journal of the American Chemical Society, 1985, 107(3):556-562], causing people's attention, but the compound has poor solubility [Gautrot, J.E., et al., New Journal of Chemistry, 2007.31(9):1585-1593], and has strong aggregation induction Luminescent, so the application in the field of organic solar cells is limited

Method used

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  • Tetracyano-anthraquinone dimethane micromolecular receptor material as well as preparation method and application thereof
  • Tetracyano-anthraquinone dimethane micromolecular receptor material as well as preparation method and application thereof
  • Tetracyano-anthraquinone dimethane micromolecular receptor material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Example 1 Compound I-1: Synthesis of 11,11,12,12-tetracyano-2-(4`-butoxyphenoxymethyl)-9,10-anthraquinone dimethane (prepared according to Scheme 1 get)

[0060] 1.1 Synthesis of 4-butoxyphenol

[0061]

[0062] Add 26.4 g (0.24 mol) of hydroquinone, 27.4 g (0.2 mol) of n-bromobutane, 8.8 g (0.22 mol) of sodium hydroxide and 125 mL of N,N-dimethylformamide In a 500mL round-bottomed flask, heat to 60°C for 12 hours; naturally cool to room temperature, pour into 500mL of ice water, extract with ethyl acetate (3×100mL), and wash the organic phase with water (3×100mL). Magnesium sulfate water was dried overnight, and the solid obtained after the solvent was removed was recrystallized with petroleum ether, suction filtered, and vacuum-dried at 50°C for 10 hours to obtain 11.3 grams of product, the yield was 34%, and the melting point was 62-64°C; IR(KBr Tablet, cm -1 ):3404.36,3354.21,2956.87,2931.8,2916.37,2872.01,2374.37,2345.44,1606.7,1541.12,1514.12,1477.47,1456.26...

Embodiment 2

[0078] Example 2 Compound I-1: Synthesis of 11,11,12,12-tetracyano-2-(4`-butoxyphenoxymethyl)-9,10-anthraquinone dimethane (prepared according to Scheme 2 get)

[0079] 2.1 Synthesis of 4-butoxyphenol

[0080]

[0081] Add 26.4 g (0.24 mol) of hydroquinone, 27.4 g (0.2 mol) of n-bromobutane, 8.8 g (0.22 mol) of sodium hydroxide and 125 mL of N,N-dimethylformamide In a 500mL round-bottomed flask, heat to 60°C for 12 hours; naturally cool to room temperature, pour into 500mL of ice water, extract with ethyl acetate (3×100mL), and wash the organic phase with water (3×100mL). Magnesium sulfate water was dried overnight, and the solid obtained after the solvent was removed was recrystallized with petroleum ether, suction filtered, and vacuum-dried at 50°C for 10 hours to obtain 11.3 grams of product, the yield was 34%, and the melting point was 62-64°C; IR(KBr Tablet, cm -1 ):3404.36,3354.21,2956.87,2931.8,2916.37,2872.01,2374.37,2345.44,1606.7,1541.12,1514.12,1477.47,1456.26...

Embodiment 3

[0098] With reference to the synthetic method of embodiment 1 or embodiment 2, the specific compound structure is synthesized, as shown in the following table:

[0099]

[0100]

[0101] Table 1

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Abstract

The invention relates to a tetracyano-anthraquinone dimethane micromolecular acceptor material as well as a preparation method and application thereof. The structure of the acceptor material is as shown in a formula I, which is described in the specification. The micromolecular acceptor material has good solubility and stability, the absorption spectrum is well matched with the solar spectrum, andthe micromolecular acceptor material can be used for organic solar cells.

Description

technical field [0001] The invention relates to the field of organic materials, in particular to a class of tetracyanoanthraquinone dimethane-based small-molecule acceptor materials, a preparation method and application thereof. Background technique [0002] In today's increasingly prominent energy problems, how to manufacture low-cost, high-efficiency solar cells has become the starting point of many scientific researches. Organic solar cells (OSC) are due to their huge diversity of organic systems, low raw material costs, low production costs, The advantages of low energy consumption and compatibility with flexible substrates have become research hotspots in recent years. Through the efforts of scientific researchers, in just two decades, its photoelectric conversion efficiency has increased from 10 -2 -10 -3 % increased to 17.3% [L. Meng, Y. Zhang, X. Wan, et al. Science, 10.1126 / science.aat2612 (2018)], but compared with the conversion efficiency of inorganic solar cel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/37C09K11/06H01L51/42H01L51/46
CPCC07C255/37C09K11/06C07C2603/24H10K85/615H10K30/00Y02E10/549
Inventor 霍二福程伟琴冯明王毅楠王延花王柏楠邵国斌汪心想师传兴杨献红邢文听韩娟郭骏付小勇常书浩董光霞王静王泽涛王宏力
Owner HENAN CHEM IND RES INST
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