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Method for synthesizing N,N,N',N'-tetra-aryl biphenyl diamine compounds through oxidative coupling of ceriums ammonium nitrate and triarylamine

A technology of aryl biphenyl diamine and ammonium cerium nitrate, which is applied in the preparation of amino compounds from amines, chemical instruments and methods, organic chemistry, etc., can solve the problems of low efficiency, harsh conditions, high cost of raw materials, etc., and achieve rapid reaction , mild conditions, low cost effect

Inactive Publication Date: 2010-09-15
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to overcome the disadvantages of harsh conditions, low efficiency or high raw material cost in the existing methods for synthesizing TPD compounds, and provide a method for synthesizing TPD by oxidative coupling of triarylamine with ammonium cerium nitrate with mild reaction conditions, high efficiency and convenience. compound-like approach

Method used

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  • Method for synthesizing N,N,N',N'-tetra-aryl biphenyl diamine compounds through oxidative coupling of ceriums ammonium nitrate and triarylamine
  • Method for synthesizing N,N,N',N'-tetra-aryl biphenyl diamine compounds through oxidative coupling of ceriums ammonium nitrate and triarylamine
  • Method for synthesizing N,N,N',N'-tetra-aryl biphenyl diamine compounds through oxidative coupling of ceriums ammonium nitrate and triarylamine

Examples

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Effect test

Embodiment 1

[0029] At room temperature (25°C), in a three-liter three-necked flask equipped with mechanical stirring, dissolve 27.3 grams (0.1 moles) of 2,4-dimethyltriphenylamine in 400 milliliters of dichloromethane; stir vigorously and add After 109.6 grams (0.2 moles) of ceric ammonium nitrate, add 60 milliliters of deionized water; continue to vigorously stir for 8 minutes at room temperature; after quenching the reaction with 250 milliliters of saturated potassium carbonate solution, separate the organic phase; Extract with methane, combine the organic phases and dry with anhydrous magnesium sulfate; filter, evaporate dichloromethane in the filtrate on a rotary evaporator, pour into 200 ml of anhydrous methanol, and stir vigorously; filter and dry to obtain 25 grams of solid powder Dissolve the solid powder with 60 milliliters of toluene, filter, and after steaming off the toluene in the filtrate on a rotary evaporator, pour into about 100-150 milliliters of anhydrous methanol, stir ...

Embodiment 2

[0031] According to the method and steps described in Example 1, only 0.1 mole of 2,4-dimethyltriphenylamine was dissolved in 500 ml of dichloromethane. Finally, 21.4 grams of white powdery N, N'-diphenyl-N, N'-di(2,4-xylyl)-1,1'-biphenyl-4,4'-diamine target product was obtained (Yield 78%). Melting point 104-105°C (literature value: 108-109°C).

Embodiment 3

[0033] According to the method and steps described in Example 1, only 0.1 mole of 2,4-dimethyltriphenylamine was dissolved in 600 ml of dichloromethane. Finally, 20.6 grams of white powdery N,N'-diphenyl-N,N'-di(2,4-xylyl)-1,1'-biphenyl-4,4'-diamine target product was obtained (Yield 75%). Melting point 104-105°C (literature value: 108-109°C).

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Abstract

The invention relates to a method for preparing N,N,N',N'-tetra-aryl biphenyl diamine (TPD) compounds, in particular to a method for synthesizing the N,N,N',N'- tetra-aryl biphenyl diamine compounds through the oxidative coupling of ceriums ammonium nitrate and triarylamine. In the method, the triarylamine available on the market is used as a raw material, the low-cost ceriums ammonium nitrate isused as a reaction reagent, and dichloromethane and water are used as solvents to synthesize the N,N,N',N'-tetra-aryl biphenyl diamine compounds efficiently at room temperature. The method overcomes the defects of rigorous conditions (high reaction temperature and long time), multiple secondary reactions, difficult after-treatment and the like of general Ullmann reaction, and also overcome the defects of high cost, difficult large-scale preparation and the like of reaction catalyzed by noble metal palladium.

Description

technical field [0001] The invention relates to a method for preparing N, N, N', N'-tetraaryl biphenyl diamine (TPD) compounds, in particular to the synthesis of N, N, N', N'- The method of tetraaryl biphenyl diamine compound. Background technique [0002] Optoelectronics technology is an emerging technology developed after electronic technology. Together with bioengineering and material science, it constitutes the three booming technology industries today. Optoelectronic materials are the basis and premise of optoelectronic technology, and organic optoelectronic materials are currently the most concerned optoelectronic materials. At present, both developed and developing countries have invested a lot of manpower and funds in the research and development of the design and synthesis of organic optoelectronic materials and their related applications. [0003] N,N,N',N'-Tetraarylbiphenyldiamine (TPD) compounds are important organic hole transport materials, which have a wide ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/54C07C211/56C07C209/68C09K11/06
Inventor 高彩艳曹兴波杨联明
Owner INST OF CHEM CHINESE ACAD OF SCI
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