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N-substituted bis-benzimidazole-containing polyimide, polyimide film, and preparation method and application of N-substituted bis-benzimidazole-containing polyimide

A technology of benzimidazole polyimide and polyimide film, which is applied in semiconductor/solid-state device manufacturing, photovoltaic power generation, electrical components, etc. Imine application and other issues

Inactive Publication Date: 2021-04-20
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the thermal expansion coefficient of traditional polyimide films is much larger than that of copper foil or silicon substrate, which greatly limits the further application of polyimide in optoelectronic materials.
[0003] The methods currently used to reduce the thermal expansion coefficient of polyimide are: (1) obtain polyimide with tight molecular packing by using aromatic dianhydride or diamine monomer with rigid structure, and this ordered molecular packing can reduce The coefficient of thermal expansion of polyimide, such as the Chinese invention patent whose publication number is CN105037769A, but this method is limited to the reduction of the coefficient of thermal expansion, and the coefficient of thermal expansion is still more than 15ppm / k; (2) adopting inorganic nanometer with low coefficient of thermal expansion The particles are blended with polyimide precursor polyamic acid, and then thermally imidized, such as the Chinese invention patents with publication numbers CN1258690A and CN101289542A. This method can reduce the thermal expansion coefficient of the polyimide film, but there are The phenomenon of uneven dispersion or even agglomeration of inorganic nanoparticles will not only reduce the product yield, but also sacrifice the mechanical properties of the polyimide film

Method used

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  • N-substituted bis-benzimidazole-containing polyimide, polyimide film, and preparation method and application of N-substituted bis-benzimidazole-containing polyimide
  • N-substituted bis-benzimidazole-containing polyimide, polyimide film, and preparation method and application of N-substituted bis-benzimidazole-containing polyimide
  • N-substituted bis-benzimidazole-containing polyimide, polyimide film, and preparation method and application of N-substituted bis-benzimidazole-containing polyimide

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preparation example Construction

[0053] The present invention provides the preparation method of polyimide film described in above technical scheme, comprises the following steps:

[0054] (1) Under protective atmosphere, diamine monomer, dianhydride monomer and organic solvent are mixed to carry out polycondensation reaction, obtain polyamic acid solution;

[0055] (2) casting the polyamic acid solution to obtain a polyamic acid wet film;

[0056] (3) performing desolventization treatment and thermal imidization on the polyamic acid wet film in sequence to obtain the polyimide film;

[0057] The diamine monomer has a structure shown in formula XI, and the dianhydride monomer has a structure shown in formula XII:

[0058]

[0059] In the invention, under the protection atmosphere, the diamine monomer, the dianhydride monomer and the organic solvent are mixed to carry out polycondensation reaction to obtain the polyamic acid solution. In the present invention, the dianhydride monomer has the structure sho...

Embodiment 1

[0103] A polyimide film, the film-forming substance is an N-substituted bisbenzimidazole polyimide with a structure shown in formula II:

[0104]

[0105] The preparation method of polyimide film is as follows:

[0106] (1) Preparation of diamine monomer 1-methyl-(2,2'-bibenzimidazole)-5,5'(6')-diamine:

[0107]

[0108] The preparation method is:

[0109] Add 50.0g of 4-nitro-1,2-phenylenediamine and 500.0g of acetic acid to the reaction flask, cool down to 10±1°C, add 69.1g of methyl 2,2,2-trichloroacetimidate dropwise, The dropwise addition was completed in 0.5-1 h, and the reaction was carried out at room temperature for 12 h, and TLC confirmed that the reaction was complete. Add 1500.0g of water to the product feed liquid, filter under reduced pressure to obtain 85g of crude product, recrystallize from ethanol, filter, and dry to obtain 68.9g of 2-trichloromethyl-5(6)-nitrobenzimidazole, yield: 84.3%;

[0110] Add 65.0g 2-trichloromethyl-5(6)-nitrobenzimidazole,...

Embodiment 2

[0116] A polyimide film, the film-forming material is N-substituted bisbenzimidazole polyimide containing structure shown in formula III:

[0117]

[0118] The preparation method of polyimide film is as follows:

[0119] (1) Preparation of diamine monomer 1-methyl-(2,2'-bibenzimidazole)-6,5'(6')-diamine:

[0120]

[0121] The preparation method is:

[0122] Add 50.0g of 4-nitro-1,2-phenylenediamine and 500.0g of acetic acid to the reaction flask, cool down to 10±1°C, add 69.1g of methyl 2,2,2-trichloroacetimidate dropwise, The dropwise addition was completed in 0.5-1 h, and the reaction was carried out at room temperature for 12 h, and TLC confirmed that the reaction was complete. Add 1,500.0 g of water to the reaction system, filter under reduced pressure to obtain 85 g of crude product, recrystallize from ethanol, filter, and dry to obtain 68.9 g of 2-trichloromethyl-5(6)-nitrobenzimidazole, yield: 84.3 %;

[0123] Add 65.0g 2-trichloromethyl-5(6)-nitrobenzimidazol...

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Abstract

The invention provides N-substituted bis-benzimidazole-containing polyimide and a polyimide film as well as a preparation method and an application thereof, and relates to the technical field of high polymer materials. The invention provides N-substituted dibenzimidazole-containing polyimide, and a polyimide film formed by taking the N-substituted dibenzimidazole-containing polyimide as a film forming matter has an extremely low thermal expansion coefficient, good mechanical properties and a relatively high glass transition temperature. The product can be effectively applied to flexible copper-clad plates and flexible solar cell substrates. The results of embodiments show that the polyimide film provided by the invention has a thermal expansion coefficient of 2.17-11.43 ppm / K, a glass transition temperature of 411-437 DEG C, a 5% thermal decomposition temperature of 547-560 DEG C, a tensile strength of 241-254 MPa and a tensile modulus of 5.6-6.9 GPa in a temperature range of 50-150 DEG C.

Description

technical field [0001] The invention relates to the technical field of polymer materials, in particular to an N-substituted bisbenzimidazole-containing polyimide and a polyimide film as well as a preparation method and application thereof. Background technique [0002] Polyimide film is an insulating material with excellent heat resistance, which is widely used in electronics, electrical engineering, aerospace and other industries. For polyimide films used in flexible copper clad laminates and flexible substrate materials for flexible solar cells, on the basis of excellent high temperature resistance, it is also necessary to have a low thermal expansion coefficient and matching with copper foil or silicon substrates. Excellent mechanical properties. However, the thermal expansion coefficient of traditional polyimide films is much larger than that of copper foil or silicon substrate, which greatly limits the further application of polyimide in optoelectronic materials. [0...

Claims

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Application Information

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IPC IPC(8): C08G73/10C08G73/18C08J5/18C08L79/08H01L51/00H01L51/42H01L51/44H05K1/03
CPCY02E10/549
Inventor 于有海陈海权陈春海钱广涛代凤娜闫晓莹
Owner DONGHUA UNIV
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