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Photovoltaic material as well as preparation method and application thereof

A photovoltaic material and difuran technology are applied in the field of naphthodifuran photovoltaic materials and their preparation, and achieve the effects of wide ultraviolet-visible absorption spectrum, high stability and stable performance

Active Publication Date: 2017-07-14
HUNAN UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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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  • Photovoltaic material as well as preparation method and application thereof
  • Photovoltaic material as well as preparation method and application thereof
  • Photovoltaic material as well as 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 difuronaphthalene photovoltaic material as well as a preparation method and application thereof, and belongs to the technical field of photovoltaic materials. The structure of the difuronaphthalene photovoltaic material is represented by a formula (I). The difuronaphthalene photovoltaic material is mainly prepared by linking a difuronaphthalene unit with another aromatic heterocycle or a derivative of the aromatic heterocycle through a carbon-carbon single bond by virtue of a stille coupling method. A synthetic route is simple and low in cost, and a synthetic method has universality and can be widely popularized and applied to synthesis of other difuronaphthalene materials. The prepared difuronaphthalene photovoltaic material has a big-pi-plane conjugate structure, so that a relatively wide ultraviolet-visible absorption spectrum can be obtained; the prepared difuronaphthalene photovoltaic material has a relatively low HOMO energy level and high oxygen stability and is beneficial to preparation of solar cell devices with relatively stable performance; the difuronaphthalene photovoltaic material has a good photovoltaic conversion function when being applied to solar cells. The structural formula (I) is as shown in the description.

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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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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