Method for preparing polyimide polymer with azo-pyrimidine structure unit

A technology of azopyrimidine and polyimide, which is applied in the field of polyimide preparation to achieve excellent thermal performance, increased light transmittance, and good photoalignment performance

Active Publication Date: 2016-06-22
南通晶爱微电子科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] How to cleverly introduce azo groups into polyimide to prepare a polyimide with good photoalignment performance and excellent thermal properties, dielectric properties and mechanical properties has not yet been solved. see the report

Method used

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  • Method for preparing polyimide polymer with azo-pyrimidine structure unit
  • Method for preparing polyimide polymer with azo-pyrimidine structure unit
  • Method for preparing polyimide polymer with azo-pyrimidine structure unit

Examples

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preparation example Construction

[0042] A preparation method of a diamine monomer comprising an azopyrimidine structure, comprising the following steps:

[0043] 1) Synthesis of 4-hydroxy-4`-substituted azobenzene: Dissolve 4-substituted aniline in a solution containing concentrated HCl / H 2 O mixed solution (the volume ratio of concentrated HCl and water is 1:3-4) in a beaker, after it is completely dissolved, place it in an ice-water bath to cool to obtain a 4-substituted aniline acid solution. Under vigorous stirring, add cold sodium nitrite aqueous solution dropwise to the 4-substituted aniline acid solution, the molar ratio of sodium nitrite and 4-substituted aniline is 1:1, to obtain the diazonium salt solution of 4-substituted aniline, And keep the temperature of this solution below 5°C. In another beaker, dissolve phenol in 10% aqueous sodium hydroxide solution, cool the alkaline solution of phenol (sodium phenate) to below 5°C in an ice-water bath, and slowly add the diazonium salt solution of 4-subs...

Embodiment 1

[0065] This embodiment prepares polyimide containing ether linkages with azopyrimidine diamine monomers, and the structural formula is as follows:

[0066]

[0067] Among them, n is 20-80;

[0068] Obtained by the following steps: 1) Synthesis of 4-hydroxy-4`-methoxyazobenzene: 4-methoxyaniline (6.1625g, 50mmol) was dissolved in 50mL concentrated HCl / H2 O(V HCl :V H2O = 1:4) in the beaker of the mixed solution, after it was completely dissolved, it was placed in an ice-water bath and cooled to below 5°C. Under vigorous stirring, 10 mL of cold sodium nitrite (3.5237 g, 50 mmol) aqueous solution was added dropwise to this solution to obtain a diazonium salt solution of 4-methoxyaniline, and the diazonium salt of 4-methoxyaniline The solution was kept below 5°C. In another beaker, phenol (4.7012g, 50mmol) was dissolved in 25mL of 10% aqueous sodium hydroxide solution, cooled to below 5°C in an ice-water bath, and the diazonium salt solution of 4-methoxyaniline was slowly A...

Embodiment 2

[0071] This example prepares biphenyl-based polyimides with azopyrimidine-containing diamine monomers, and the structural formula is as follows:

[0072]

[0073] Among them, n is 20-80;

[0074] Obtained by the following steps: 1) Synthesis of 4-hydroxyl-4'-cyanoazobenzene: 4-cyanoaniline (5.9532g, 50mmol) was dissolved in 50mL concentrated HCl / H 2 O(V HCl :V H2O = 1:4) in the beaker of the mixed solution, after it was completely dissolved, it was placed in an ice-water bath and cooled to below 5°C. Under vigorous stirring, 10 mL of cold sodium nitrite (3.5237 g, 50 mmol) aqueous solution was added dropwise to this solution to obtain a diazonium salt solution of 4-cyanoaniline, and the diazonium salt solution of 4-cyanoaniline was kept Keep below 5°C. In another beaker, dissolve phenol (4.7012g, 50mmol) in 25mL of 10% aqueous sodium hydroxide solution, cool it to below 5°C in an ice-water bath, and slowly add the diazonium salt solution of 4-cyanoaniline dropwise , an...

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Abstract

The invention relates to a method for preparing a diamine monomer with an azo-pyrimidine structure and a method for preparing a polyimide polymer by adopting the diamine monomer with the azo-pyrimidine structure. The preparation method comprises the following steps: carrying out a coupling reaction on 4-substituted aniline and sodium phenate to obtain 4-hydroxy-4'-substituted azobenzene; and carrying out nucleophilic substitution on the 4-hydroxy-4'-substituted azobenzene and dibromoalkane to generate bromo-azobenzene, and reacting the bromo-azobenzene with 4,6-diamido-2-mercaptopyrimidine to obtain the diamine monomer; and carrying out condensation polymerization on the diamine monomer with dianhydride to obtain polyimide. The pyrimidine structure is introduced into the diamine monomer, so that the charge transfer complex effect of aromatic rings of polyimide is reduced, and the glass transition temperature of the polyimide is reduced; and the azo group has photo-induced anisotropy, and an azo unit is introduced into the polyimide by alkyl chains having different lengths, so that the heterogeneous degree of the azo group can be effectively regulated, and the application of the polyimide in alignment films and other optical fields can be improved to a great extent.

Description

technical field [0001] The invention relates to the field of polyimide preparation, in particular to a method for synthesizing a diamine monomer containing an azo side chain pyrimidine structure and a method for preparing a polyimide polymer. Background technique [0002] Polyimide (Polyimide, PI), with its excellent thermal properties, chemical properties, electrical properties, mechanical properties and good adhesion to ITO conductive glass, has become a commonly used orientation for liquid crystal displays since the 1980s. agent material. Existing liquid crystal alignment agents require rubbing alignment treatment, which will generate dust and static electricity, which reduces the yield of products and limits the application in high-performance wide-viewing angle liquid crystal display devices. Therefore, non-contact alignment liquid crystal alignment The development of the film has received great attention from the liquid crystal display industry, especially the use of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/48C08G73/10
CPCC07D239/48C08G73/1085
Inventor 路庆华童发钦
Owner 南通晶爱微电子科技有限公司
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