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Diamine monomer, intrinsic type high-dielectric low-loss polyimide as well as preparation method and application of intrinsic high-dielectric low-loss polyimide

A technology of diamine monomer and polyimide, which is applied in the field of material science, can solve the problems of low dielectric constant and difficult to meet, and achieve the effect of increasing the dielectric constant, increasing the dipole moment, and excellent thermal stability

Active Publication Date: 2021-12-07
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional polyimide has a low dielectric constant (~3.5), which is difficult to meet the requirements of modern electronic information and energy technology fields

Method used

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  • Diamine monomer, intrinsic type high-dielectric low-loss polyimide as well as preparation method and application of intrinsic high-dielectric low-loss polyimide
  • Diamine monomer, intrinsic type high-dielectric low-loss polyimide as well as preparation method and application of intrinsic high-dielectric low-loss polyimide
  • Diamine monomer, intrinsic type high-dielectric low-loss polyimide as well as preparation method and application of intrinsic high-dielectric low-loss polyimide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 15g (60.02mmol) 3,5-dibromotoluene, 10.68g (60.02mmol) N-bromosuccinimide, 0.49g azobisisobutyronitrile (3mmol) were dissolved in 180mL acetonitrile, and the temperature was raised under the protection of argon Reflux at 85°C for 3h. The target product 3,5-dibromobenzyl bromide was obtained by petroleum ether column chromatography. 1 H NMR (400MHz, DMSO–d 6 ) δ 7.80 (t, J = 1.7Hz, 1H), 7.72 (d, J = 1.7Hz, 2H), 4.68 (s, 2H).

[0043] 10g (30.41mmol) 3,5-dibromobenzyl bromide, 7.49g (73.32mmol) were added to 75mL DMF, reacted at 60°C for 3 hours, poured into 1000mL saturated aqueous sodium chloride solution, a white solid precipitated, dried The target product 1,3-dibromo-5(methylsulfonylmethyl)benzene was obtained. 1 H NMR (400MHz, DMSO–d 6 ) δ 7.90 (t, J = 1.8Hz, 1H), 7.66 (d, J = 1.8Hz, 2H), 4.55 (s, 2H), 2.96 (s, 3H).

[0044] 4g (12.19mmol) 1,3-dibromo-5 (methylsulfonylmethyl) benzene, 5.08g (36.58mmol, 2.4eq) p-aminophenyl borate hydrochloride, 33mL 2M K 2 CO ...

Embodiment 2

[0052] 15g (60.02mmol) 2,5-dibromotoluene, 10.68g (60.02mmol) N-bromosuccinimide, 0.49g azobisisobutyronitrile (3mmol) were dissolved in 180mL acetonitrile, and the temperature was raised under the protection of argon Reflux at 85°C for 3h. The target product 2,5-dibromobenzyl bromide was obtained by petroleum ether column chromatography.

[0053] 10g (30.41mmol) 2,5-dibromobenzyl bromide, 7.49g (73.32mmol) were added to 75mL DMF, reacted at 60°C for 3 hours, poured into 1000mL saturated aqueous sodium chloride solution, a white solid was precipitated, after drying The target product 1,4-dibromo-2-(methylsulfonylmethyl)benzene was obtained.

[0054] 4g (12.19mmol) 1,4-dibromo-2-(methylsulfonylmethyl)benzene, 5.08g (36.58mmol, 2.4eq) p-aminophenyl borate hydrochloride, 33mL 2M K 2 CO 3 Solution, catalytic amount Pd(PPh 3 ) 4 Added to 65 mL THF. Reaction at 70°C for 48h. The target product 2'-(methylsulfonylmethyl)-(1,1':4',1"-triphenyl)-4,4"-diamine (m,o-MSMDA) was obtai...

Embodiment 3

[0062] 15g (60.02mmol) 2,6-dibromotoluene, 10.68g (60.02mmol) N-bromosuccinimide, 0.49g azobisisobutyronitrile (3mmol) were dissolved in 180mL acetonitrile, and the temperature was raised under the protection of argon Reflux at 85°C for 3h. The target product 2,5-dibromobenzyl bromide was obtained by petroleum ether column chromatography.

[0063] 10g (30.41mmol) 2,6-dibromobenzyl bromide, 7.49g (73.32mmol) were added to 75mL DMF, reacted at 60°C for 3 hours, poured into 1000mL saturated aqueous sodium chloride solution, a white solid precipitated, dried The target product 1,3-dibromo-2-(methylsulfonylmethyl)benzene was obtained.

[0064] 4g (12.19mmol) 1,3-dibromo-2-(methylsulfonylmethyl)benzene, 5.08g (36.58mmol, 2.4eq) p-aminophenyl borate hydrochloride, 33mL 2M K 2 CO 3 Solution, catalytic amount Pd(PPh 3 ) 4 Added to 65 mL THF. Reaction at 70°C for 48h. The target product 2'-(methylsulfonylmethyl)-(1,1':3',1"-triphenyl)-4,4"-diamine (o,o-MSMDA) was obtained after c...

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Abstract

The invention discloses a diamine monomer, intrinsic type high-dielectric low-loss polyimide and a preparation method and application of the intrinsic type high-dielectric low-loss polyimide, and belongs to the technical field of material science. The intrinsic high-dielectric low-loss polyimide material is prepared by taking a diamine monomer containing a sulfuryl side chain, pyromellitic dianhydride and other commercial dianhydride monomers as raw materials and performing imidization the after polymerization at room temperature, and has the advantages of high dielectric constant, low dielectric loss and excellent thermal stability. The polyimide disclosed by the invention is simple in preparation process and high in universality, and can be used for large-scale industrial production; and the polyimide prepared by the method can be applied to preparation of high-dielectric materials, can be suitable for high-tech fields such as energy storage materials, photoelectric devices and information industry, and is particularly applied to the aspect of organic field effect transistors.

Description

technical field [0001] The invention relates to the technical field of material science, in particular to a diamine monomer, an intrinsic high dielectric low-loss polyimide and a preparation method and application thereof. Background technique [0002] With the rapid development of modern electronic information technology and nanotechnology, people put forward higher requirements for the comprehensive performance of materials. Traditional high dielectric materials, as one of the key materials, have been difficult to meet the requirements of advanced electronic and electrical technology. Therefore, it is an urgent need for those skilled in the art to develop new high dielectric materials with excellent performance. The concept of high dielectric material comes from the semiconductor industry. Generally speaking, compared with silicon dioxide, materials with high dielectric constant are called high dielectric materials (>3.9). [0003] Compared with traditional inorganic m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/28C07C315/04C08G73/10
CPCC07C317/28C08G73/1007
Inventor 张艺郑维文刘川梁孝慈蒋星刘四委池振国许家瑞
Owner SUN YAT SEN UNIV
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