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Method for preparing biphenyl triarylated amine compound by taking carboxyl as guide group, intermediate and preparation method thereof

A triarylamine and biphenyl-type technology, which is applied in the synthesis field of biphenyl-type triarylamine compounds, can solve the problems of high industrial production costs, and achieve the effects of reducing industrial production costs, production costs, and reaction conditions

Active Publication Date: 2018-07-13
ZHENGZHOU SIGMA CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to provide an intermediate for the preparation of biphenyl-type triarylamine compounds, thereby solving the problem of high industrial production costs in the existing technical route for synthesizing biphenyl-type triarylamine compounds

Method used

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  • Method for preparing biphenyl triarylated amine compound by taking carboxyl as guide group, intermediate and preparation method thereof
  • Method for preparing biphenyl triarylated amine compound by taking carboxyl as guide group, intermediate and preparation method thereof
  • Method for preparing biphenyl triarylated amine compound by taking carboxyl as guide group, intermediate and preparation method thereof

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0035] The intermediate used to prepare the biphenyl type triarylamine compound in this embodiment has a structural formula as shown in formula (2):

[0036]

[0037] The method for preparing biphenyl type triarylamine compounds with carboxyl group as the guiding group in this embodiment, the process route is as follows:

[0038]

[0039] Specific steps are as follows:

[0040] 1) Synthesis of intermediates

[0041] 1. add 4.00kg water in the reactor with thermometer and reflux device, add o-chlorobenzoic acid 2.00kg, potassium carbonate 2.00kg, copper oxide 0.02kg and 3-methylaniline (1a) 1.00kg successively while stirring, Raise the temperature of the system to 100°C to react, monitor the reaction to the end by TLC, stop heating; cool the system to 60°C, add 0.16 kg of activated carbon for decolorization, continue to stir until the system is uniform, then filter, and then add concentrated 30-36% Adjust the pH of the filtrate to 1 with hydrochloric acid. At this time,...

Embodiment 2

[0046] The intermediate used to prepare the biphenyl triarylamine compound in this example has the same structural formula as in Example 1.

[0047] The method for preparing biphenyl triarylamine compounds with carboxyl as the guiding group in this embodiment, the process route is as follows:

[0048]

[0049] Specific steps are as follows:

[0050] 1) Synthesis of intermediates

[0051] 1. add 10.05kg water in the reactor with thermometer and reflux device, add o-chlorobenzoic acid 2.00kg, sodium carbonate 4.50kg, copper oxide 0.11kg and 3-methylaniline (1a) 1.30kg successively while stirring, Raise the temperature of the system to 103°C to react, monitor the reaction to the end by TLC, stop heating; cool the system to 70°C, add 0.20 kg of activated carbon, continue to stir until the system is uniform, then filter, then add concentrated hydrochloric acid with a concentration of 35% to adjust the pH value of the filtrate =1, at this time, a product is precipitated, and th...

Embodiment 3

[0056] The intermediate used to prepare the biphenyl triarylamine compound in this example has the same structural formula as in Example 1.

[0057] The method for preparing biphenyl triarylamine compounds with carboxyl as the guiding group in this embodiment, the process route is as follows:

[0058]

[0059] Specific steps are as follows:

[0060] 1) Synthesis of intermediates

[0061] 1. add 20.00kg water in the reactor with thermometer and reflux device, add 2.00kg o-chlorobenzoic acid, cesium carbonate 7.00kg, copper powder 0.10kg, copper oxide 0.10kg and 3-methylaniline ( 1a) 1.60kg, raise the temperature of the system to 105°C to react, monitor the reaction to the end point by TLC, stop heating; cool the system to 80°C, add 0.24kg of activated carbon, continue to stir until the system is uniform and then filter, then add concentrated hydrochloric acid with a concentration of 36% Adjust the pH value of the filtrate to 1. At this time, a product is precipitated. The ...

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Abstract

The invention relates to a method for preparing a biphenyl triarylated amine compound by taking carboxyl as a guide group, an intermediate and a preparation method thereof. The intermediate has a structure as shown in the formula, (the formula is shown in the description), wherein R is selected from hydrogen, alkyl with a carbon atom number of 1-10, halogenated alkyl with a carbon atom number of 1-5, alkoxy with a carbon atom number of 1-5 and aryl. The intermediate is prepared from simple and easily available raw materials, and the biphenyl triarylated amine compound prepared by the intermediate is high in purity and yield, so that the production cost of the biphenyl triarylated amine compound can be remarkably reduced, and therefore, the method is very suitable for industrial productionof the biphenyl triarylated amine compound.

Description

technical field [0001] The invention belongs to the field of synthesizing biphenyl triarylamine compounds, and in particular relates to a method for preparing biphenyl triarylamine compounds with a carboxyl group as a guiding group, an intermediate and a preparation method thereof. Background technique [0002] In organic hole transport materials, triarylamine compounds can form ammonium ion radicals under the action of an electric field, making them have high hole mobility and good hole transport properties. The currently developed triarylamine hole transport materials mainly include triphenylamine and its derivatives, biphenyl triarylamine compounds, and triarylamine containing fluorene rings in the molecule. Among them, the alkyl-substituted biphenyl triarylamine compound not only has high hole mobility and stability, but also has a large solubility in the resin due to the non-polar group such as methyl in the molecule, and is not easy to Exuded from organic resins. At ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C227/18C07C229/58C07C209/68C07C211/54C07C211/58
CPCC07C209/68C07C229/58C07C211/54C07C211/58
Inventor 胡孝伦王英豪杨勇申丽坤高永琪赵萍萍
Owner ZHENGZHOU SIGMA CHEM
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