Polyimide precursor resin as well as preparation method and application thereof

A polyimide precursor and resin technology, applied in the field of polymer materials, can solve the problems of decreased mechanical properties of films, unsuitable polyimide, film residues, etc., to avoid high stress residues, excellent mechanical properties and thermal properties. The effect of stability

Active Publication Date: 2022-03-29
SHENZHEN INST OF ADVANCED TECH CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In above-mentioned four kinds of prior art, the shortcoming of one-step method is that the kind of applicable polyimide is very limited, is only applicable to soluble polyimide, for the polyimide of homophenylene, biphenyl type widely used at present not applicable
There are two major disadvantages in the curing accelerator method. First, the addition of low-temperature curing accelerators will cause its residue in the film. Due to the residue of these accelerators, the mechanical properties of polyimide will be negatively affected to varying degrees...

Method used

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  • Polyimide precursor resin as well as preparation method and application thereof
  • Polyimide precursor resin as well as preparation method and application thereof
  • Polyimide precursor resin as well as preparation method and application thereof

Examples

Experimental program
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Effect test

preparation example 1

[0058] A diamine monomer, 4,4'-pyrazine-diphenylamine, has the following structure:

[0059]

[0060] The preparation method comprises the following steps:

[0061]

[0062] Place 54mmol of 4-aminophenylboronic acid ester, 27mmol of 2,5-dibromopyrazine, 3.24mmol of tetrakistriphenylphosphopalladium and 67.5mmol of potassium carbonate in a reaction flask, keep it under a nitrogen atmosphere, and add 140mL of solvent (a mixed solvent of toluene, ethanol and water with a volume ratio of 4:1:1); under a nitrogen atmosphere, stir and heat up to 100°C and react for 24h. After the reaction was completed, it was washed 3 times with saturated brine, dried by adding anhydrous sodium sulfate, and the liquid was removed under vacuum. Separated by column chromatography, the target product was obtained with a yield of 63%.

[0063] Characterization results of 4,4'-pyrazine-diphenylamine:

[0064] 1 H-NMR (400MHz, DMSO-d 6 ): δ(ppm)8.95(s,2H),7.85(d,J 2 =12.0Hz,4H),6.67(d,J 2 =8...

preparation example 2

[0066] A diamine monomer with the following structure:

[0067]

[0068] The preparation method comprises the following steps:

[0069]

[0070] 46mmol 1,4-phenylenediamine, 23mmol 2,5-dibromopyrazine, 2.3mmol tridibenzylideneacetone dipalladium, 4.6mmol dicyclohexyl[3,6-dimethoxy-2',4 ',6'-triisopropyl[1,1'-biphenyl]-2-yl]phosphine (Brettphos), 92mmol sodium tert-butoxide was placed in the reaction flask, kept under nitrogen atmosphere, and 250mL of toluene was added, Under a nitrogen atmosphere, the temperature was raised to 90° C. and reacted for 24 h. After the reaction was completed, the solvent was removed under vacuum, and the target product was obtained by ethanol recrystallization with a yield of 51%.

[0071] The characterization result of described diamine monomer:

[0072] 1 H-NMR (400MHz, DMSO-d 6 ): δ (ppm) 7.74 (m, 6H), 7.54 (m, 4H), 7.0 (m, 2H), 6.75 (m, 4H).

Embodiment 1

[0074] A polyimide precursor resin PAA1 obtained by polycondensation of 4,4'-pyrazine-diphenylamine (preparation example 1) and 3,3',4,4'-biphenyltetracarboxylic dianhydride; specific preparation method as follows:

[0075] Under dry nitrogen flow, dissolve 0.05mol 4,4'-pyrazine-diphenylamine in 100mL N,N-dimethylacetamide, add 0.05mol 3,3',4,4'-biphenyltetracarboxylic acid diphenylamine Anhydride, reacted at 0°C for 1h, then raised the temperature to 25°C and continued to react for 12h. After completion of the reaction, polyimide precursor resin PAA1 was obtained.

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Abstract

The invention provides polyimide precursor resin as well as a preparation method and application thereof. The polyimide precursor resin is obtained through polycondensation of a diamine monomer and aromatic tetracarboxylic dianhydride. The diamine monomer comprises at least one compound with a structure as shown in a formula I and is a diamine monomer containing an aza-aromatic ring, the diamine monomer with the structure can be subjected to an autocatalytic reaction in a heated and cured polyimide precursor resin, the imidization reaction process is accelerated, and the reaction time is shortened. The imidization rate of the polyimide precursor resin at low temperature is obviously improved. The polyimide precursor resin can be cured at low temperature to obtain a polyimide film with excellent mechanical property and thermal stability, so that high stress residue caused by high-temperature curing is effectively avoided; therefore, the application requirements of the polyimide precursor resin in low-temperature processing environments such as microelectronic chip materials, packaging materials and interlayer dielectric layers are fully met.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and in particular relates to a polyimide precursor resin and its preparation method and application. Background technique [0002] Polyimide has excellent mechanical properties, good heat resistance, chemical corrosion resistance, radiation resistance and good film-forming properties, and is widely used in various fields. In the field of semiconductor electronics, polyimide can be used in α-particle shielding layers, stress buffer layers, interlayer dielectric materials or photosensitive rewiring materials, etc. These materials play an important role that cannot be replaced in the modern microelectronics semiconductor industry. The traditional polyimide precursor resin must be heated and cured at least 300-400 ° C to make it play the ideal performance of polyimide. Such high-temperature processing conditions greatly limit its application range in the field of microelectronics. For exam...

Claims

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Application Information

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IPC IPC(8): C08G73/10C08J5/18C08L79/08G03F7/004G03F7/027G03F7/038
CPCC08G73/1085C08G73/1067C08G73/1071C08G73/1042C08G73/1007C08J5/18G03F7/004G03F7/027G03F7/0387C08J2379/08C08G73/10C08L79/08G03F7/038
Inventor 李长青
Owner SHENZHEN INST OF ADVANCED TECH CHINESE ACAD OF SCI
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