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Asymmetric aromatic diamine monomer containing terphenyl large substituent side groups and polyimidecontaining terphenyl large substituent side groups

A polyimide, aromatic diamine technology, applied in the preparation of amino compounds, the preparation of organic compounds, organic chemistry and other directions, can solve the problems of low molar polarizability, thermal stability and mechanical property loss, and achieve easy The effect of industrialization, easy purification and separation, and simple synthesis route

Pending Publication Date: 2021-08-20
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

PI containing alicyclic substituents and fluorine-containing groups usually has the characteristics of low molar polarizability and high molar volume, but its thermal stability and mechanical properties will be lost to a certain extent

Method used

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  • Asymmetric aromatic diamine monomer containing terphenyl large substituent side groups and polyimidecontaining terphenyl large substituent side groups
  • Asymmetric aromatic diamine monomer containing terphenyl large substituent side groups and polyimidecontaining terphenyl large substituent side groups
  • Asymmetric aromatic diamine monomer containing terphenyl large substituent side groups and polyimidecontaining terphenyl large substituent side groups

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Experimental program
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Effect test

Embodiment 1

[0052] (1) Preparation of asymmetric aromatic diamine monomers containing terphenyl large substituted side groups

[0053] (a) Under nitrogen protection, 19.76g (8mmol) of 2,4-dinitrobromobenzene, 24.12g (88mmol) of 3,5-diphenylboronic acid, 1.85g (0.16mmol) of four ( Triphenylphosphine) palladium joins in the there-necked flask of 500mL, adds respectively 150mL volume ratio and is the mixed solvent of 2:1 toluene and ethylene glycol dimethyl ether and the sodium carbonate solution of 120mL 1mol / L, heats up after stirring at room temperature for half an hour Reaction at 100°C for 8h, after the reaction was completed, the intermediate compound 3,5-(diphenyl)phenyl-2,4-dinitrobenzene was obtained by suction filtration, drying and further recrystallization, with a yield of 91% ( Here the yield is obtained by the ratio of the mass of the intermediate compound actually obtained to the mass of the intermediate compound obtained theoretically).

[0054] (b) Add 18.82g (0.05mol) of t...

Embodiment 2

[0058] (1) Preparation of aromatic diamine monomer containing terphenyl large substituted side group asymmetric structure

[0059] (a) Under nitrogen protection, 19.76g (8mmol) of 2,4-dinitrobromobenzene, 24.12g (88mmol) of 3,5-diphenylphenylboronic acid, 2.10g (0.18mmol) of four ( Triphenylphosphine) palladium joins in the there-necked flask of 1000mL, adds respectively 320mL volume ratio is the mixed solvent of 4:1 toluene and ethylene glycol dimethyl ether and the sodium carbonate solution of 240mL 2mol / L, heats up after stirring at room temperature for half an hour Reaction at 110°C for 7h, after the reaction was completed, the intermediate compound 3,5-(diphenyl)phenyl-2,4-dinitrobenzene was obtained by suction filtration, drying and further recrystallization, with a yield of 88% ( Here the yield is obtained by the ratio of the mass of the intermediate compound actually obtained to the mass of the intermediate compound obtained theoretically).

[0060] (b) Add 18.82g (0....

Embodiment 3

[0064] (1) Preparation of aromatic diamine monomer containing terphenyl large substituted side group asymmetric structure

[0065] (a) Under nitrogen protection, 14.82g (6mmol) of 2,4-dinitrobromobenzene, 18.09g (66mmol) of 3,5-diphenylboronic acid, 1.39g (0.13mmol) of four ( Triphenylphosphine) palladium joins in the there-necked flask of 500mL, adds respectively 250mL volume ratio and is the mixed solvent of 3:1 toluene and ethylene glycol dimethyl ether and the sodium carbonate solution of 150mL 2mol / L, heats up after stirring at room temperature for half an hour Reaction at 100°C for 10h, after the reaction was completed, the intermediate compound 3,5-(diphenyl)phenyl-2,4-dinitrobenzene was obtained by suction filtration, drying and further recrystallization, with a yield of 89% ( Here the yield is obtained by the ratio of the mass of the intermediate compound actually obtained to the mass of the intermediate compound obtained theoretically).

[0066] (b) Add 10.16g (0.03...

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Abstract

The invention belongs to the field of high polymer materials, and relates to an asymmetric aromatic diamine monomer containing terphenyl large substituent side groups and polyimide containing terphenyl large substituent side groups. 2, 4-dinitrobromobenzene reacts with 3, 5-diphenyl phenylboronic acid according to a molar ratio under an alkaline condition to obtain an intermediate compound, and the intermediate, the dinitro compound is reduced through a reduction reaction to obtain the asymmetric aromatic diamine monomer 3, 5-(diphenyl) phenyl-2, 4-diaminobenzene containing the terphenyl large substituted structure. The diamine monomer and a commercial aromatic dianhydride monomer which are equal in substance amount are added into an organic solvent, the solution is stirred to react under the action of a catalyst, and settling, washing and drying are performed to obtain the fibrous asymmetric structure polyimide containing the terphenyl large substituted side groups. The solubility of the polyimide in a specific solvent can reach more than 30wt%, the polyimide has excellent film-forming property, and a prepared polymer film has potential application value in the field of microelectronics.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and in particular relates to a class of asymmetric aromatic diamine monomers and polyimides containing large terphenyl-substituted side groups. Background technique [0002] Polyimide (PI), as a widely used high-performance polymer material, has unique structural characteristics and excellent comprehensive properties. Functionalized PI films can be used in high-tech fields such as gas separation membranes, flexible optoelectronic device substrates, motor insulation, microelectronics manufacturing and packaging. With the rapid development of the microelectronics industry, the wire density of integrated circuits continues to increase, resulting in problems such as slow signal transmission and increased power loss. In order to solve this problem, it is necessary to require the insulating layer material of integrated circuits to have a lower dielectric The constant k (1.6 ~ 2.8), but the d...

Claims

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Application Information

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IPC IPC(8): C07C211/51C07C209/32C07C201/12C07C205/06C08G73/10C08J5/18C08L79/08
CPCC07C211/51C07C209/325C07C201/12C08G73/1071C08G73/1067C08G73/1007C08J5/18C08J2379/08C07C205/06
Inventor 汪称意郑慧陶正旺赵晓燕朱冠南华广洲李坚任强
Owner CHANGZHOU UNIV
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