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Multi-cyano substituted triphenylamine derivatives and synthesis method and use thereof

A cyano-substituted, triphenylamine technology, applied in a class of polycyano-substituted triphenylamine derivatives and its synthesis and application, can solve the problem of low efficiency of organic solar cells

Active Publication Date: 2015-05-20
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the efficiency of organic solar cells has long been low, which is inseparable from its fundamental physical process

Method used

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  • Multi-cyano substituted triphenylamine derivatives and synthesis method and use thereof
  • Multi-cyano substituted triphenylamine derivatives and synthesis method and use thereof
  • Multi-cyano substituted triphenylamine derivatives and synthesis method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1. Preparation of 2-(4-(diphenylamino)phenyl)-1,1,4,4-tetracyano-1,3-butadiene (MTCBD)

[0047]

[0048] (1). Under nitrogen protection, p-iodotriphenylamine is mixed with acetylene, wherein the molar ratio of p-iodotriphenylamine to acetylene is 2: 3; add catalyst amount of bistriphenylphosphine palladium dichloride and catalyst amount Cuprous iodide, then the mixture is mixed with triethylamine, and refluxed under stirring; the crude product is obtained by filtration, and through silica gel column chromatography, p-ethynyl triphenylamine is obtained, and the productive rate is about 90%;

[0049] (2). Under nitrogen protection, the p-ethynyltriphenylamine obtained in step (1) is mixed with tetracyanoethylene in a molar ratio of 1:1, and then the mixture is stirred at room temperature in dichloromethane for 16 hours, After recrystallization from its n-hexane solution, the target product was obtained with a yield of about 95%.

[0050] m / z: 397.13 (100.0%), ...

Embodiment 2

[0056] Example 2. 2-(4-(Diphenylamino)phenyl)-1,1,3,4,4-pentacyano-1,3-butadiene (MPCBD)

[0057]

[0058] (1). Under the protection of nitrogen, mix 4-iodo-triphenylamine and propionitrile, wherein, the molar ratio of 4-iodo-triphenylamine and propionitrile is 2:3; Phosphorous palladium dichloride and cuprous iodide of catalytic amount, then the mixture is mixed with triethylamine, and refluxed under stirring; the crude product is obtained by filtration, recrystallized through its petroleum ether solution, to obtain the target product, and the yield is about 80%;

[0059] (2). Under the protection of nitrogen, the product obtained in step (1) is mixed with tetracyanoethylene in a molar ratio of 1:1, and then the mixture is stirred at room temperature in dichloromethane for 20 hours, and first passed through a silica gel column Chromatography gave the target product with a yield of about 85%.

[0060] m / z: 422.13 (100.0%), 423.13 (31.6%), 424.13 (4.8%).

[0061] Preparat...

Embodiment 3

[0066] Example 3. 2-(4-(Di-p-toluidyl)phenyl)-1,1,4,4-tetracyano-1,3-butadiene (DTMTCBD)

[0067]

[0068](1). Under nitrogen protection, mix 4-iodo-N, N-di-p-toluidine and acetylene, wherein the molar ratio of 4-iodo-N, N-di-p-toluidine to acetylene is 2:3; Add a catalytic amount of bistriphenylphosphine palladium dichloride and a catalytic amount of cuprous iodide, then mix the mixture with triethylamine, and reflux under stirring; filter to obtain a crude product, which is subjected to silica gel column chromatography to obtain The target product, the yield is about 83%;

[0069] (2). Under nitrogen protection, the product obtained in step (1) is mixed with tetracyanoethylene in a molar ratio of 1:1, and then the mixture is stirred at room temperature in dichloromethane for 18 hours, and then the mixture is stirred with normal hexane The solution was recrystallized to obtain the target product with a yield of about 80%.

[0070] m / z: 425.16 (100.0%), 426.17 (30.5%), 42...

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Abstract

The invention belongs to the field of organic light-sensitive and / or electron transport materials in organic solar cell devices, in particular to multi-cyano substituted triphenylamine derivatives for organic light-sensitive and / or electron transport materials, a synthesis method thereof, and use of the multi-cyano substituted triphenylamine derivative materials as organic solar cell devices. Through molecular design, triphenylamine is taken as a main framework and multi-cyano groups with high electron withdrawing ability are introduced, so that charge transfer in molecules is strong. Therefore, the energy gap is reduced, and the aims that the light absorption range is wide and a light absorption peak value is positioned at a long wavelength are fulfilled. Meanwhile, the molecules have high electron-capturing capacity and can be applied to the organic light-sensitive layer and / or electron transport layer materials for organic solar cells. The multi-cyano substituted triphenylamine derivatives have the structure shown in the description.

Description

technical field [0001] The invention belongs to the field of organic photosensitive and / or electron-transporting materials in organic solar cell devices, in particular to a class of polycyano-substituted triphenylamine derivatives used in organic photosensitive and / or organic electron-transporting materials and a synthesis method thereof, as well as using The use of the polycyano-substituted triphenylamine derivative material as an organic photosensitive layer and / or an electron transport layer material of an organic solar cell device and the like. Background technique [0002] With the rapid development of the economy in today's world, energy issues have attracted more and more attention. The energy crisis caused by the depletion of fossil fuels and the greenhouse effect caused by the burning of fossil fuels have brought great challenges to the human living environment. Solar energy, which accounts for more than 99% of the total energy of the earth, has gradually entered p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/42C07D213/36C07C253/30H01L51/46H01L51/44H01L51/42H01L51/05H01L51/10H01L51/30H01S5/36
CPCY02E10/549
Inventor 汪鹏飞汤响林刘卫敏
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI