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A [2.1.3] benzoselenodiazole photovoltaic material and its preparation method and application

A technology of benzoselenodiazole and photovoltaic materials, applied in photovoltaic power generation, semiconductor/solid-state device manufacturing, organic chemistry, etc., with good application prospects, wide ultraviolet-visible absorption spectrum, high carrier mobility, and high stability Effect

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

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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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  • A [2.1.3] benzoselenodiazole photovoltaic material and its preparation method and application
  • A [2.1.3] benzoselenodiazole photovoltaic material and its preparation method and application
  • A [2.1.3] benzoselenodiazole 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]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] benzoselenodiazole 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 [2.1.3]benzoselenodiazole photovoltaic material. This type of photovoltaic material is mainly prepared by the stille coupling method, and the [2.1.3] benzoselenodiazole unit is connected with another electron donor unit thiophene benzofuran through a carbon-carbon single bond to obtain [2.1 .3] Benzoselenodiazole organic small molecule materials. The synthesis route is simple, the cost is low, and the synthesis method is universal, and it can be widely applied to the synthesis of other [2.1.3] benzoselenoadiazole materials; [2.1.3] benzoselenoadiazoles Photovoltaic materials have larger conjugated structures, which are expected to obtain wider UV-visible absorption spectra and carrier mobility; and [2.1.3] benzoselenodiazole 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] 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 Patents(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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