A kind of perylene imide compound and its preparation method and application

A technology of perylene imide and compound, applied in the field of polymer synthesis, can solve problems such as large charge loss, and achieve the effects of wide absorption, improved electron mobility, and excellent thermal stability

Active Publication Date: 2019-05-03
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But it is easy to form a larger aggregate phase, resulting in a larger charge loss

Method used

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  • A kind of perylene imide compound and its preparation method and application
  • A kind of perylene imide compound and its preparation method and application
  • A kind of perylene imide compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Take 3,3',5,5'-biphenyltetraboronic acid pinacol ester (1.52mmol, 1g), N,N'-bis(2-ethylpropyl)-1-bromo-perylenediimide Amine (8eq, 12.16mmol, 7.41g), 200mg Pd(PPh 3 ) 4 、K 2 CO 3 The mixed solution (containing 200mL toluene, 8mL ethanol, where K 2 CO 3 Concentration is 2mol / L) in a 500mL flask, after passing nitrogen, raise the temperature to 80°C, react for 48h, then dilute the reaction solution with dichloromethane and wash with saturated brine, collect the organic layer and dry it, then remove the dichloromethane by rotary evaporation , and then carried out column chromatography with petroleum ether / dichloromethane as the eluent to obtain 1.9 g of the target product (molecular formula shown in 3a below), with a yield of 54%.

[0026]

Embodiment 2

[0028] Take 3,3',5,5'-biphenyltetraboronic acid pinacol ester (1.52mmol, 1g), N,N'-diisooctyl-1-bromo-7-perylenediimide (8eq , 12.16mmol, 8.43g), 200mg Pd(PPh 3 ) 4 and K 2 CO 3 The mixed solution (containing 200mL toluene, 8mL ethanol, where K 2 CO 3 The concentration is 2mol / L) was placed in a 500mL flask, and after nitrogen was passed through, the temperature was raised to 80°C, and the reaction was carried out for 48h. Then dilute the reaction solution with dichloromethane and wash with saturated brine, collect the organic layer and dry it, then remove the dichloromethane by rotary evaporation and use petroleum ether / dichloromethane as eluent for column chromatography to obtain the compound 3b with the following structural formula ( 2.5 g, 63.2%).

[0029]

Embodiment 3

[0031] Take 3,3',5,5'-biphenyltetraboronic acid pinacol ester (1.52mmol, 1g), N,N'-di(2-pentylhexyl)-1-bromo-perylenediimide (8eq, 12.16mmol, 9.46g), 200mg Pd(PPh 3 ) 4 and K 2 CO 3 The mixed solution (containing 200mL toluene, 8mL ethanol, where K 2 CO 3 The concentration is 2mol / L) was placed in a 500mL flask, and after nitrogen was passed through, the temperature was raised to 80°C, and the reaction was carried out for 48h. Then dilute the reaction solution with dichloromethane and wash with saturated brine, collect the organic layer and dry it, then remove the dichloromethane by rotary evaporation and use petroleum ether / dichloromethane as eluent for column chromatography to obtain the compound 3c (3.09g , 73.2%).

[0032]

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Abstract

The present invention involves a pyride amine compound and its preparation method.One.The preparation method includes the following steps: mixing the mixed phenyl borne and 1‑ bromine pyrine.As a solvents, a pyrumine amine compound was obtained by the Suzuki puppet coupler at 60 作为90 ° C.Small molecules provided by the present invention have a large co -pyramid structure and three -dimensional structure, which can achieve multi -dimensional charge transmission. It has high electronic migration rates.High, suitable for large -scale production.

Description

technical field [0001] The invention belongs to the technical field of polymer synthesis, and relates to a perylene imide compound and a preparation method and application thereof. Background technique [0002] With the gradual depletion of petroleum and other energy sources, the development and application of renewable energy such as solar energy has gradually become the focus of social attention. The main way to utilize solar energy is to develop solar cells. However, traditional silicon-based solar cells are expensive, have a long energy repayment time, complex preparation procedures, and are prone to pollution during the production process. In comparison, organic solar cells and perovskite solar cells have the incomparable advantages of silicon-based solar cells, such as light weight, low price, easy processing, and large-area devices, and are increasingly valued by relevant researchers. [0003] Perylene imide compounds have great potential when applied to solar cells....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00H01L51/42H01L51/46
CPCC07D519/00H10K85/6572H10K30/00H10K2102/00Y02E10/549
Inventor 刘治田吴瑶高翔张林骅於凌峰张旗
Owner WUHAN INSTITUTE OF TECHNOLOGY
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