[2.1.3] benzoselenadiazole photovoltaic material as well as preparation method and application thereof

A technology of benzoselenadiazole and photovoltaic materials, which is used in photovoltaic power generation, semiconductor/solid-state device manufacturing, electrical components and other directions to achieve the effect of optimizing photovoltaic performance

Active Publication Date: 2017-10-24
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 BSe as an acceptor unit coupled with other aromatic heterocyclic donor units in organic small molecule solar cells.

Method used

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  • [2.1.3] benzoselenadiazole photovoltaic material as well as preparation method and application thereof
  • [2.1.3] benzoselenadiazole photovoltaic material as well as preparation method and application thereof
  • [2.1.3] benzoselenadiazole photovoltaic material as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0043] Step 1) Under the protection of argon, compound 1 (3.13g, 5.24mmol), 2-(tri-n-butyl)thiophene (4.84g, 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 48 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 2.85g of orange solid compound 2, and the reaction yield was 90%;

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

[0045] TOF-MS...

Embodiment 2

[0066] The preparation of n-octyloxy group-[2.1.3]benzoselenadiazole-thiophene benzofuran (M1) comprises the following steps:

[0067] Step 1) Under the protection of argon, compound 1 (3.13g, 5.24mmol), 2-(tri-n-butyl)thiophene (3.90g, 10.48mmol), anhydrous toluene (150mL) were added into a 250mL three-necked flask, Then continue to add tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ) (0.81g, 0.70mmol), after completion, reflux at 85°C for 60 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 3:1 to obtain 2.70 g of orange solid compound 2, and the reaction yield was 85%;

[0068] The characterization of the compound 2 is as fo...

Embodiment 3

[0090] The preparation of n-octyloxy group-[2.1.3]benzoselenadiazole-thiophene benzofuran (M1) comprises the following steps:

[0091] Step 1) Under argon protection, compound 1 (3.13g, 5.24mmol), 2-(tri-n-butyl)thiophene (5.85g, 15.72mmol), and anhydrous toluene (150mL) were added to a 250mL three-necked flask, Then continue to add tetrakis (triphenylphosphine) palladium (Pd (PPh 3 ) 4 ) (0.69g, 0.60mmol), after completion, reflux at 95°C for 40 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 5:1 to obtain 2.50 g of orange solid compound 2, and the reaction yield was 79%;

[0092] The characterization of the compound 2 is as follows:

...

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Abstract

The invention discloses a [2.1.3] benzoselenadiazole photovoltaic material as well as a preparation method and application thereof, belonging to the technical field of photovoltaic materials. The structure of the [2.1.3] benzoselenadiazole photovoltaic material is shown in the formula (I). The invention also provides the preparation method and application of the [2.1.3] benzoselenadiazole photovoltaic material. In preparation of the photovoltaic material, a stille coupling method is mainly used for connecting a [2.1.3] benzoselenadiazole unit with another electron donor unit thiophene benzofuran through carbon-carbon single bonds, so as to obtain a [2.1.3] benzoselenadiazole organic small molecule material. The synthetic route is simple, the cost is low, and the synthetic method has universality and can be better popularized and applied to synthesis of other [2.1.3] benzoselenadiazole materials; the [2.1.3] benzoselenadiazole photovoltaic material has a larger conjugated structure and is hopeful to obtain wider ultraviolet-visible absorption spectrum and carrier mobility; and the [2.1.3] benzoselenadiazole photovoltaic material has a lower HOMO level, has high stability to oxygen, and is favorable for preparing a solar battery device with more stable performance. The structural formula is shown in the specification.

Description

technical field [0001] The invention relates to the technical field of photovoltaic materials, in particular to a [2.1.3] benzoselenodiazole photovoltaic material and its preparation method and application. Background technique [0002] In the past five years, organic small molecule solar cells have achieved rapid development, and their photovoltaic performance has reached the level of polymer solar cells [Jiaoyan Zhou, Yi Zuo, Xiangjian Wan, Guankui Long, Qian Zhang, Wang Ni, Yongsheng Liu, Zhi Li, Guangrui He, Chenxi Li, Bin Kan, Miaomiao Li, Yongsheng Chen. Journal of the American Chemical Society. 2013, 135, 8484.]. However, there are still relatively few types of high-performance small-molecule photovoltaic materials, so it is necessary to design and synthesize more types of organic small-molecule photovoltaic materials, and further optimize photovoltaic performance through structural modification. [0003] [2.1.3] Benzoselenodiazole (BSe) is an important electron acce...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04H01L51/42H01L51/46
CPCC07D495/04H10K85/655H10K85/656H10K85/657H10K30/00Y02E10/549
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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