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Method for preparing 4-nitrotriphenylamine

A technology of nitrotriphenylamine and p-fluoronitrobenzene, which is applied in the field of preparation of 4-nitrotriphenylamine, can solve the problems of high solvent toxicity, long reaction time, and high reaction temperature, and achieve low solvent toxicity and short reaction time , the effect of high yield

Inactive Publication Date: 2009-09-23
EAST CHINA UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Technical problem to be solved by the present invention In order to overcome the existing 4-nitrotriphenylamine preparation method high reaction temperature, many by-products, long reaction time, high solvent toxicity and difficult industrialization defects, and provide a low reaction temperature, A preparation method with few by-products, short reaction time, low solvent toxicity, high yield and purity, low cost and easy industrialization

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Under argon protection, in a 100ml Schlenk bottle, add 30ml N,N-dimethylacetamide (DMAC), then add 1.69g (10.0mmol) diphenylamine, and add 900mg (30.0mmol) 80wt % sodium hydride (NaH) (commercially available, the remaining 20wt% is mineral oil), fully stirred until no bubbles are produced, then added 2.11g (15.0mmol) p-fluoronitrobenzene, and stirred at room temperature (25°C) , TLC detects that the diphenylamine reactant is consumed until the end of the reaction. After the reaction is over, distillation under reduced pressure reclaims N,N-dimethylacetamide (DMAC), and then 30ml of water is added. Solids are precipitated, filtered, and the obtained crude product is weighed with absolute ethanol. Crystallized to obtain product 2.50g, yield: 86.1%, 1 HNMR (500Hz, CDCl 3 ) δ: 6.92 (d, J=7.1Hz, 2H), 7.17-7.22 (m, 6H), 7.34-7.38 (m, 4H), 8.03 (d, J=7.1Hz, 2H); melting point (m.p.): 142-144°C, 98.6% purity.

Embodiment 2

[0021] In a 100ml Schlenk bottle, add 30ml N,N-dimethylacetamide (DMAC), then add 1.69mg (10.0mmol) diphenylamine, and add 1.92g (20.0mmol) sodium tert-butoxide ( t-BuONa), after fully stirring, then add 2.11g (15.0mmol) p-fluoronitrobenzene, stir and react at room temperature (10°C), TLC detects that the diphenylamine reactant is consumed, and after the reaction is over, distillation under reduced pressure reclaims N , N-dimethylacetamide (DMAC), plus 30ml of water, solids were precipitated, filtered, and the obtained crude product was recrystallized with absolute ethanol to obtain 2.35g of the product, yield: 80.9%, purity 98.4%.

Embodiment 3

[0023] Under argon protection, in a 100ml Schlenk bottle, add 30ml dimethyl sulfoxide (DMSO), then add 1.69g (10.0mmol) diphenylamine, and add 600mg (20.0mmol) 80wt% sodium hydride after the diphenylamine is completely dissolved (NaH), stir well until no bubbles are generated, then add 2.11g (15.0mmol) p-fluoronitrobenzene, stir and react at room temperature (30°C), until the diphenylamine reactant is consumed by TLC, depressurize after the reaction Recover dimethyl sulfoxide (DMSO) by distillation, add 30ml of water, solid precipitates, filter, and recrystallize the obtained crude product with absolute ethanol to obtain 2.40g of product, yield: 82.7%, purity: 98.1%.

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PUM

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Abstract

The invention discloses a method for preparing 4-nitrotriphenylamine, which comprises the following steps that: diphenylamine and alkali are reacted in an organic solvent, then fluoronitrobenzene is added into the organic solvent; and the product is obtained by reaction at 10 to 30 DEG C; and the organic solvent is one or more of dimethyl sulfoxide, N, N-dimethyl acetamide, dimethylimidazolidinone and methylpyrrolidone. The method preferably selects the solvent to ensure that the reaction can be performed at room temperature and has no byproducts, is simple and effective, has low cost, convenient use of raw materials, short reaction time and high yield, and is easy to apply to industrialized production.

Description

technical field [0001] The invention relates to a method for synthesizing an intermediate of a triarylamine hole transport material, in particular to a method for preparing 4-nitrotriphenylamine. Background technique [0002] Hole transport materials are an important part of organic electroluminescent devices. So far, small molecule hole transport materials mainly include pyrazoline derivatives, carbazole derivatives, and triarylamine derivatives. Among them, triarylamine materials have good electron donating properties, low ionization potential, high hole mobility, good solubility and amorphous film formation, and strong fluorescence properties and photostability. And other characteristics, it is widely used as a hole transport material in photoconductors, organic light-emitting diodes (OLEDs), organic solar cells, photorefractive holography, field effect transistors, and many other fields. [0003] Since the nitro group can be easily converted into other functional groups...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/56C07C209/60
Inventor 陶晓春杨兴淮黄应钊孙杰蔡良珍曹雄杰朱哲
Owner EAST CHINA UNIV OF SCI & TECH
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