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Diamine monomer containing spirofluorene functional group, preparation method thereof and polyimide with low dielectric constant

A technology of functional groups and diamine monomers, which is applied in the field of polyimide with low dielectric constant, can solve the problems of high dielectric constant and low dielectric constant of polyimide, improve dimensional stability, The effect of lowering the dielectric constant and compensating for the lowering of the glass transition temperature

Active Publication Date: 2021-02-26
GUANGDONG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In order to solve the technical problem of high dielectric constant of the existing common polyimide, the present invention provides a diamine monomer containing spirofluorene functional group Body and preparation method thereof, polyimide with low dielectric constant

Method used

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  • Diamine monomer containing spirofluorene functional group, preparation method thereof and polyimide with low dielectric constant
  • Diamine monomer containing spirofluorene functional group, preparation method thereof and polyimide with low dielectric constant
  • Diamine monomer containing spirofluorene functional group, preparation method thereof and polyimide with low dielectric constant

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Embodiment 1

[0043] The structural formula of the diamine monomer (1,3-SFDA) containing the spirofluorene functional group in this embodiment is as follows figure 1 Shown, concrete synthetic steps are as follows (as figure 2 ):

[0044] (1) Under a nitrogen atmosphere, mix 2,7-dibromofluorenone (8g, 23.68mmol), 1-naphthol (20.46g, 142.04mmol) and methanesulfonic acid (6.2mL, 94.688mmol) at 150°C Heated and stirred for 24h. After the reaction was completed, the reaction mixture was poured into water and extracted with dichloromethane. The organic layer was dried with anhydrous magnesium sulfate, filtered, and separated by column chromatography after decompression distillation to remove the solvent. The eluent was a mixed solvent of sherwood oil and dichloromethane to obtain a yellow solid with a yield of about 60% (8.4 g).

[0045] (2) Under a nitrogen atmosphere, tetrakis(triphenylphosphine)palladium (169mg, 0.44mmol) was added to the yellow solid (4g, 6.8mmol) obtained in step (1), 3-(...

Embodiment 2

[0049] The structural formula of the diamine monomer (1,4-SFDA) containing the spirofluorene functional group in this embodiment is as follows Figure 4 Shown, concrete synthetic steps are as follows (as Figure 5 ):

[0050] (1) Under a nitrogen atmosphere, tetrakis(triphenylphosphine)palladium (169mg, 0.44mmol) was added to the yellow solid (4g, 6.8mmol) obtained in step (1) of Example 1, 4-( 4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (3.4g, 14.64mmol), aqueous sodium carbonate (2M, 15mL, 30mmol), toluene ( 250mL) and ethanol (15mL) in a mixture. The reaction was heated to 90°C and stirred overnight. After cooling to room temperature, the reaction mixture was introduced into water and extracted with dichloromethane. The organic layer was dried with anhydrous magnesium sulfate, filtered, separated by column chromatography after decompression distillation to remove the solvent, and the eluent was a mixed solvent of sherwood oil and dichloromethane to obtain the ta...

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Abstract

The invention provides a diamine monomer containing a spirofluorene functional group, a preparation method thereof and polyimide with a low dielectric constant. The diamine monomer containing the spirofluorene functional group has the following chemical structural formula, R1 is a spirofluorene unit, and R2 is an aromatic amino group. A spirofluorene functional unit with a spatial torsion structure and relatively large steric hindrance is introduced into the diamine monomer, and the dielectric constant of the prepared polyimide is reduced by increasing gaps among molecular chains and the freevolume of the structure; meanwhile, the rigid structure of the spirofluorene functional unit is beneficial to make up for the reduction of the glass-transition temperature of polyimide caused by the reduction of the acting force between molecular chains, and is also beneficial to the improvement of the dimensional stability of the polyimide film. In addition, the diamine monomer containing the spirofluorene functional group is simple and convenient to synthesize and prepare, and commercial application is facilitated.

Description

technical field [0001] The invention relates to the technical field of low dielectric constant polyimide, in particular to a diamine monomer containing spirofluorene functional groups, a preparation method thereof, and a low dielectric constant polyimide. Background technique [0002] The fifth generation mobile communication technology (5G) will become one of the important industries for the future development of our country. It is predicted that by 2025, the market size of 5G-related products and services will reach 15 trillion US dollars, among which, the dielectric materials with low dielectric constant and low dielectric loss involved will exceed 30,000 tons, with more than 300 billion market potential. Therefore, it is of great significance to develop dielectric materials with low dielectric constant, low dielectric loss and low water absorption. [0003] Polyimide (PI) has the advantages of good mechanical properties, high electrical and chemical stability, high tem...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/96C08G73/10
CPCC07D311/96C08G73/1085Y02E10/549
Inventor 谭婉怡刘屹东闵永刚廖松义
Owner GUANGDONG UNIV OF TECH
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