Intrinsical fluorinated photosensitive polyimide resin and its preparation method

A photosensitive polyimide resin, an intrinsic type technology, is applied in the field of intrinsic type fluorinated photosensitive polyimide resin and its preparation, and achieves the effects of low water absorption, tolerant photolithography conditions and good storage stability

Inactive Publication Date: 2007-05-30
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Ciba-Geigy company (US 4657832) improves its solubility by introducing bridged ring substituents on the benzene ring structure of aromatic diamine afterwards; US 4698295 discloses a class of intrinsic type photosensitive polyimide resin, which uses The organic tetraacid dianhydride of a plurality of carbonyls replaces the ketone anhydride

Method used

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  • Intrinsical fluorinated photosensitive polyimide resin and its preparation method
  • Intrinsical fluorinated photosensitive polyimide resin and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1、1

[0034] Example 1, 1,1-bis(4'-amino-3',5'-bis(methyl)phenyl)-1-(3',5'-bis(trifluoromethyl)phenyl)- Synthesis of 2,2,2-trifluoroethane

[0035] 65 grams of 2,6-dimethylaniline, 35 grams of 2,6-dimethylaniline hydrochloride and 35 grams of 3',5'-bis(trifluoromethyl)-2,2,2 trifluoroacetophenone grams were mixed well in the reaction vial. The mixture was heated to 130°C for 1 hour until the starting material was completely dissolved. The reaction mass was then heated to reflux at 180°C for 10 hours. The temperature of the reaction system was cooled to room temperature, and 100 g of 20% sodium hydroxide solution was dropped into the reaction solution. Then the solution was distilled with steam for 4 hours, the insoluble matter was filtered and washed with water, then dried and recrystallized with ethanol to obtain a pure product with a reaction yield of 49%.

[0036] Product melting point: 151°C;

[0037] Infrared (KBr, cm -1 ): 3494 (N-H absorption peak), 3403 (N-H amino abso...

Embodiment 2、1

[0042] Example 2, 1,1-bis(4'-amino-3',5'-di(methyl)phenyl)-1-(4'-trifluoromethylphenyl)-2,2,2- Synthesis of trifluoroethane

[0043] 100 grams of 2,6-dimethylaniline, 40 grams of 2,6-dimethylaniline hydrochloride and 50 grams of 4'-trifluoromethyl-2,2,2 trifluoroacetophenone are mixed in a reaction flask uniform. The mixture was heated to 120°C for 1.5 hours until the starting material was completely dissolved. The reaction mass was then heated to reflux at 170°C for 8 hours. The temperature of the reaction system was cooled to room temperature, and 100 g of 20% potassium hydroxide solution was dropped into the reaction solution. Then the solution was distilled with steam for 4 hours, the insoluble matter was filtered and washed with water, then dried and recrystallized with ethanol to obtain a pure product.

[0044] Product melting point: 162°C;

[0045] NMR-H spectroscopy (300 MHz, DMSO-d 6 , δ): 2.3(S; 12H), 4.8(S; 4H), 6.5(S; 4H), 7.0(D; 2H), 7.4(D; 2H);

[0046] NM...

Embodiment 3、1

[0048] Example 3, 1,1-bis(4'-amino-3',5'-di(methyl)phenyl)-1-(3'-trifluoromethylphenyl)-2,2,2- Synthesis of trifluoroethane

[0049] Mix 80 grams of 2,6-dimethylaniline, 25 grams of 2,6-dimethylaniline hydrochloride and 45 grams of 3'-trifluoromethyl-2,2,2 trifluoroacetophenone in a reaction flask uniform. The mixture was heated to 120°C for 2 hours until the starting material was completely dissolved. The reaction mass was then heated to reflux at 170°C for 12 hours. The reaction system was cooled to room temperature, and 100 g of 20% ammonia solution was dropped into the reaction solution. Then distill the solution with water steam for 4 hours, filter the insoluble matter and wash with water, after drying, use petroleum ether-ethyl acetate (volume ratio 1:1) mixture as eluent, and obtain pure product by silica gel column chromatography .

[0050] Product melting point: 149°C;

[0051] NMR-H spectroscopy (300 MHz, DMSO-d 6 , δ): 2.4(S; 12H), 4.0(S; 4H), 6.6(S; 4H), 7.1...

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Abstract

The invention discloses an intrinsic-typed photoactive polyimide resin and making method, which is polycondensated by 3,3',4,4' -benzophenone pyromellitic dianhydride 40 with polyalkyl substituted aromatic methane diamine 20-42 as fluorine aromatic lateral group, wherein the carbon atom number of A, B, C and D in the formula I is 1-10; E, F, G is H atom or trifluoromethyl. The invention possesses superior solubility, which can be reserved for half year under indoor temperature and 18 months under 4 deg.c.

Description

technical field [0001] The invention relates to an intrinsic type fluorinated photosensitive polyimide resin and a preparation method thereof. Background technique [0002] Polyimide material has the advantages of high temperature resistance, low temperature resistance, corrosion resistance, high insulation, low dielectric constant and low dielectric loss, excellent mechanical properties, etc., and has been widely used as a passivation layer film for semiconductor chips and microelectronic packaging Insulation layer film, dielectric layer film, stress buffer protective layer film, interlayer dielectric of multilayer metal interconnection structure, insulating diaphragm and flexible circuit board, etc. In these applications, it is often necessary to form a conductive channel between the circuit on one side of the polyimide film layer and the circuit or device on the other side by means of ultraviolet lithography, so it is necessary to manufacture channels or channels on the p...

Claims

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Application Information

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IPC IPC(8): C08G73/10
Inventor 杨士勇李洪深范琳刘金刚
Owner INST OF CHEM CHINESE ACAD OF SCI
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