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A [2.1.3] benzoxadiazole-based photovoltaic material and its preparation method and application

A technology of benzoxadiazole and photovoltaic materials, applied in photovoltaic power generation, semiconductor/solid-state device manufacturing, organic chemistry, etc., to achieve low HOMO energy level, simple synthesis route, and high stability

Active Publication Date: 2019-07-30
GUANGZHOU YUEWANG AGRI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on the application of BO as an acceptor unit coupled with other aromatic heterocyclic donor units in organic small molecule solar cells.

Method used

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  • A [2.1.3] benzoxadiazole-based photovoltaic material and its preparation method and application
  • A [2.1.3] benzoxadiazole-based photovoltaic material and its preparation method and application
  • A [2.1.3] benzoxadiazole-based photovoltaic material and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The preparation of n-octyloxy group-[2.1.3]benzoxadiazole-thiophene benzofuran (M1) comprises the following steps:

[0043] Step 1) Under argon protection, compound 1 (3.13g, 5.24mmol), 2-(tri-n-butyl)furan (4.64g, 13.00mmol), anhydrous toluene (150mL) were added into a 250mL three-necked flask, Then continue to add tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ) (0.74g, 0.64mmol), after completion, reflux at 90°C for 24 hours. After the reaction, cool to room temperature, pour the reaction mixture into water, extract 3 times with dichloromethane, dry the organic phase, filter, and remove excess organic solvent to obtain the crude compound 2, which is rinsed with a silica gel column , the eluent used for rinsing was a mixture of petroleum ether and dichloromethane with a volume ratio of 4:1 to obtain 2.49g of orange solid compound 2, and the reaction yield was 94%;

[0044] The characterization of the compound 2 is as follows:

[0045] TOF-MS: m / z=509;

[...

Embodiment 2

[0064] The preparation of n-octyloxy group-[2.1.3]benzoxadiazole-thiophene benzofuran (M1) comprises the following steps:

[0065] Step 1) Under the protection of argon, compound 1 (3.13g, 5.24mmol), 2-(tri-n-butyl)furan (3.74g, 10.48mmol), anhydrous toluene (150mL) were added into a 250mL three-necked flask, Then continue to add tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ) (0.92g, 0.8mmol), after completion, reflux at 85°C for 30 hours. After the reaction, cool to room temperature, pour the reaction mixture into water, extract 3 times with dichloromethane, dry the organic phase, filter, remove excess organic solvent, obtain the crude compound 2, and pour the crude compound 2 through a silica gel column. The eluent used for washing and rinsing was a mixed solution of n-hexane and dichloromethane with a volume ratio of 7:1 to obtain 2.37g of orange solid compound 2, and the reaction yield was 89%;

[0066] The characterization of the compound 2 is as follows:

...

Embodiment 3

[0086] The preparation of n-octyloxy group-[2.1.3]benzoxadiazole-thiophene benzofuran (M1) comprises the following steps:

[0087] Step 1) Under the protection of argon, compound 1 (3.13g, 5.24mmol), 2-(tri-n-butyl)furan (6.55g, 18.34mmol), anhydrous toluene (150mL) were added into a 250mL three-necked flask, Then continue to add tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ) (0.58g, 0.50mmol), after completion, reflux at 95°C for 20 hours. After the reaction, cool to room temperature, pour the reaction mixture into water, extract 3 times with dichloromethane, dry the organic phase, filter, remove excess organic solvent, obtain the crude compound 2, and pour the crude compound 2 through a silica gel column. The eluent used for washing and rinsing was a mixture of petroleum ether and chloroform with a volume ratio of 6:1 to obtain 2.13g of orange solid compound 2, and the reaction yield was 80%;

[0088] The characterization of the compound 2 is as follows:

[008...

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Abstract

The invention discloses a [2.1.3] benzoxadiazole photovoltaic material and its preparation method and application, belonging 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 [2.1.3]benzoxadiazole photovoltaic material. The preparation of this type of photovoltaic material is mainly through the stille coupling method to synthesize a type of [2.1.3] benzoxadiazole (BO) organic electron donor unit whose terminal group is trifluoromethylphenyl, changing the different sides chain units to regulate the optical and electrochemical properties of organic molecules. The synthesis route is simple, the cost is low, and the synthesis method is universal, which can be well extended and applied to the synthesis of other [2.1.3] benzoxadiazole materials; [2.1.3] benzoxadiazoles Photovoltaic materials have larger conjugated structures, which are expected to obtain wider UV-visible absorption spectra and carrier mobility; and [2.1.3] benzoxadiazole photovoltaic materials have lower HOMO energy levels, which are beneficial to Oxygen has high stability, which is conducive to the preparation of solar cell devices with more stable performance.

Description

technical field [0001] The invention relates to the technical field of photovoltaic materials, in particular to a [2.1.3] benzoxadiazole photovoltaic material and its preparation method and application. Background technique [0002] With the increasing global energy crisis, countries around the world are turning their attention to renewable clean energy. Therefore, technologies aimed at efficient utilization of solar energy have attracted more and more attention from the scientific and industrial circles. As a device for converting solar energy into electrical energy, organic small molecule solar cells have developed rapidly in the past five years, and their energy conversion efficiency has exceeded 10% [Bin Kan, Qian Zhang, Miaomiao Li, Xiangjian Wan, Wang Ni, Guankui Long , Yunchuang Wang, Xuan Yang, Huanran Feng, Yongsheng Chen. Journal of the American Chemical Society, 2014, 136, 15529]. However, there are few types of small-molecule photovoltaic materials with high pe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04H01L51/42H01L51/46
CPCC07D495/04H10K85/653H10K85/655H10K85/657H10K30/00H10K2102/00Y02E10/549
Inventor 刘波陈远道王晓波王钢刘骏胡霞何敏周诗彪
Owner GUANGZHOU YUEWANG AGRI CO LTD
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