A kind of naphthodifuran photovoltaic material and preparation method and application thereof

A photovoltaic material, difuran technology, applied in photovoltaic power generation, semiconductor/solid-state device manufacturing, organic chemistry, etc., to achieve the effect of wide ultraviolet-visible absorption spectrum, high stability and stable performance

Active Publication Date: 2020-01-03
HUNAN UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Judging from the research work reported publicly in the literature, NDF has not been reported in the field of organic small molecule solar cells

Method used

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  • A kind of naphthodifuran photovoltaic material and preparation method and application thereof
  • A kind of naphthodifuran photovoltaic material and preparation method and application thereof
  • A kind of naphthodifuran photovoltaic material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The preparation of 3,7-dinonyl-naphthodifuran-2,6-bis(2,5-diisooctyl-3,6-thienyl-2-pyrrolopyrrole dione (M1), including the following step:

[0038] Step 1) Under argon protection, 1,5-dihydroxynaphthalene (3.20g, 20.0mmol), 1-bromo-2-undecanone (11.2g, 45mmol), anhydrous potassium carbonate (8g, 58mmol) mixed solution In 100ml of anhydrous acetonitrile, heat and reflux for 4 hours; after the reaction is completed, cool to room temperature and pour into water, extract with dichloromethane, wash the mixed phase with water, dry over anhydrous magnesium sulfate, and then spin dry the organic phase to obtain the crude compound 1 , the crude product was rinsed through a silica gel column, and the eluent used in the rinse was a mixed solution of dichloromethane and petroleum ether with a volume ratio of 10:1 to obtain 7.4g of light yellow solid compound 1, and the reaction yield was 75%;

[0039] The characterization of the compound 1 is as follows:

[0040] GC-MS: m / z=497;...

Embodiment 2

[0059] The preparation of 3,7-dinonyl-naphthodifuran-2,6-bis(2,5-diisooctyl-3,6-thienyl-2-pyrrolopyrrole dione (M1), including the following step:

[0060] Step 1) Under argon protection, 1,5-dihydroxynaphthalene (3.20g, 20.0mmol), 1-bromo-2-undecanone (12.44g, 50mmol), and anhydrous potassium carbonate (4.14g, 30mmol) were mixed Dissolve in 100ml of anhydrous acetonitrile, heat and reflux for 3.5 hours; after the reaction is completed, cool to room temperature and pour into water, extract with dichloromethane, wash the mixed phase with water, dry over anhydrous magnesium sulfate, and spin dry the organic phase to obtain compound 1 The crude product was washed through a silica gel column, and the eluent used in the washing was a mixture of dichloromethane and petroleum ether with a volume ratio of 8:1 to obtain 7.5 g of light yellow solid compound 1 with a reaction yield of 77%;

[0061] The characterization of the compound 1 is as follows:

[0062] GC-MS: m / z=497;

[0063]...

Embodiment 3

[0081] The preparation of 3,7-dinonyl-naphthodifuran-2,6-bis(2,5-diisooctyl-3,6-thienyl-2-pyrrolopyrrole dione (M1), including the following step:

[0082] Step 1) Under argon protection, 1,5-dihydroxynaphthalene (3.20g, 20.0mmol), 1-bromo-2-undecanone (11.94g, 48mmol), and anhydrous potassium carbonate (6.07g, 44mmol) were mixed Dissolve in 100ml of anhydrous acetonitrile, heat and reflux for 4.5 hours; after the reaction is completed, cool to room temperature and pour into water, extract with dichloromethane, wash the mixed phase with water, dry over anhydrous magnesium sulfate, and spin dry the organic phase to obtain compound 1 The crude product was washed through a silica gel column, and the eluent used in the washing was a mixture of dichloromethane and n-hexane with a volume ratio of 9:1 to obtain 7.3 g of light yellow solid compound 1 with a reaction yield of 74%;

[0083] The characterization of the compound 1 is as follows:

[0084] GC-MS: m / z=497;

[0085] 1 H N...

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Abstract

The invention discloses a naphthodifuran photovoltaic material, a preparation method and application thereof, and belongs to the technical field of photovoltaic materials. Its structure is represented by formula (I). The invention also provides a preparation method and application of the naphthodifuran photovoltaic material. This type of photovoltaic material is mainly prepared by the stille coupling method, in which the naphthodifuran unit is connected with another aromatic heterocycle or its derivatives through a carbon-carbon unit. The synthesis route is simple, the cost is low, and the synthesis method is universal, and can be better popularized and applied to the synthesis of other naphthodifuran materials. The prepared naphthodifuran photovoltaic material has a large π-plane conjugated structure, which can obtain a wider ultraviolet-visible absorption spectrum; and has a lower HOMO energy level, high stability to oxygen, and is conducive to preparation performance A more stable solar cell device; when the naphthodifuran photovoltaic material is applied to a solar cell, it has a good photoelectric conversion function.

Description

technical field [0001] The invention relates to the technical field of photovoltaic materials, in particular to a naphthodifuran photovoltaic material and its preparation method and application. Background technique [0002] An ideal organic small molecule electron donor unit needs to have a broad absorption spectrum to obtain a high short-circuit current, and a deep HOMO energy level to obtain a high open-circuit voltage and stability. The method of donating-accepting unit combination has been proved to be the most effective way to obtain wide absorption and deep HOMO energy level of organic small molecules and improve photovoltaic performance. At present, benzodifuran (BDF) polymer photovoltaic materials have shown good photovoltaic performance [Bo Liu, Beibei Qiu, Xuewen Chen, LuXiao, Yongfang Li, Yuehui He, Lihui Jiang, Yingping Zou. Polymer Chemistry, 2014 , 5, 5002-5008; Bo Liu, Xuewen Chen, Yingping Zou, Lu Xiao, Xinjun Xu, Yuehui He, Lidong Li, and Yongfang Li. Macr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00H01L51/46
CPCC07D519/00H10K85/655H10K85/6574H10K85/6572Y02E10/549
Inventor 刘波陈远道王晓波王钢刘骏周诗彪胡霞何敏
Owner HUNAN UNIV OF ARTS & SCI
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