# US 2010/0167208 A1 · Water soluble photosensitive polymide polymer, its preparation and photoresist containing the same

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- Number: US 2010/0167208 A1
- Document ID: US20100167208A1
- Status: Published application
- Kind: A1
- Application number: 12/421,973
- Filed: 2009-04-10
- Published: 2010-07-01
- Earliest claimed: 2008-12-30
- Assignees: Chang Chun Plastics Co., Ltd.
- Inventors: Jen FU WANG; Sheng Yen Wu; An Pang Tu; Kuen Yuan Hwang
- Web page: https://patentgrep.com/patent/US20100167208A1

## CPC

- C08G 73/106: {containing silicon}
- C08G 73/1007: {from tetracarboxylic acids or derivatives and diamines}
- C08G 73/1014: {in the form of (mono)anhydrid}
- C08G 73/1042: {Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds}
- C08G 73/1082: {wholly aromatic in the tetracarboxylic moiety}
- C08G 73/12: Unsaturated polyimide precursors
- C08L 79/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08L 79/085: {Unsaturated polyimide precursors}
- G03F 7/037: the binders being polyamides or polyimides
- G03F 7/0757: {Macromolecular compounds containing Si-O, Si-C or Si-N bonds (G03F7/0752 takes precedence)}
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)

## Abstract

The present invention relates to a water soluble photosensitive polyimide polymer, preparation thereof and a photoresist composition containing the same. The water soluble photosensitive polyimide polymer is characterized by having repeat units represented by the following formula (I): the other symbols are defined in the specification].

## Claims

### Claim 1

A water soluble photosensitive polyimide polymer which is characterized in that it possesses the repeat units represented by formula (I):
R1 represents a tetra-valence organic group having 4 or more carbon atoms; R2 is a three- or tetra-valence organic group, which is optionally substituted with carboxyl group; R3 represents a two- to tetra-valence organic group; A represents OH or COOH group; R4 and R5 are the same or different, each represents an alkylene group having 1˜6 carbon atoms, an arylene group, arylalkylene group, arylene-oxy-alkylene group having 6˜20 carbon atoms; R7 and R8 are the same or different, each represents the group selected from a hydrogen, a halogen, a carboxyl, a linear or cyclic alkyl having 1˜20 carbon atoms, an aryl, alkylaryl, and arylalkyl having 6˜20 carbon atoms; R9 represents a hydrogen atom or an alkyl group having 1-6 carbon atoms; x represents an integer of 1 or 2; y represents an integer of 0, 1 or 2; a, b and n each represents an integer equal to or greater than 1; m and k each represents an integer equal to or greater than 0]; wherein the above repeating units are in random or block arrangement.

### Claim 2 (depends on 1)

The water soluble photosensitive polyimide polymer according to claim 1, wherein the polyimide polymer has a weight average molecular weight of from 10,000 to 300,000, an intrinsic viscosity of from 0.20 to 0.95, a 5% thermal weight loss temperature (Td(95%)) of not less than 260° C.

### Claim 3 (depends on 1)

The water soluble photosensitive polyimide polymer according to claim 1, wherein when said water soluble photosensitive polyimide polymer is cast into a film having a thickness of 10˜25 μm, the film with a dimension of 9 cm×5.5 cm is dissolved in 1000 ml 1 wt % of aqueous sodium carbonate solution within 2 minutes.

### Claim 4

A process for producing water soluble photosensitive polyimide polymer having repeating units represented by formula (I):
R1 represents a tetra-valence organic group having 4 or more carbon atoms; R2 is a three- or tetra-valence organic group, which is optionally substituted with carboxyl group; R3 represents a two- to tetra-valence organic group; A represents OH or COOH group; R4 and R5 are the same or different, each represents an alkylene group having 1˜6 carbon atoms, an arylene group, arylalkylene group, arylene-oxy-alkylene group having 6˜20 carbon atoms; R7 and R8 are the same or different, each represents the group selected from a hydrogen, a halogen, a carboxyl, a linear or cyclic alkyl having 1˜20 carbon atoms, an aryl, alkylaryl, and arylalkyl having 6˜20 carbon atoms; R9 represents a hydrogen atom or an alkyl group having 1-6 carbon atoms; x represents an integer of 1 or 2; y represents an integer of 0, 1 or 2; a, b and n each represents an integer equal to or greater than 1; m and k each represents an integer equal to or greater than 0]; wherein the above repeating units are in random or block arrangement;
the process comprises the following steps:
(a) reacting a tetra-carboxyl acid dianhydride with a diamine having carboxyl and/or hydroxyl functional groups to obtain a polyamic acid precursor having carboxyl and/or hydroxyl functional groups in the main chain; wherein the molar ratio of tetra-carboxyl acid dianhydride: diamine is 1:0.8˜1:1.2;
(b) heating and subjecting the polyamic acid precursor having carboxyl and/or hydroxyl functional groups in the main chain obtained from step (a) to cyclization to obtain a polyimide having carboxyl and/or hydroxyl functional groups in the main chain; and
(c) reacting the polyimide having carboxyl and/or hydroxyl functional groups in the main chain obtained from step (b) with a dianhydride of the following formula (II) to subject to open-ring reaction:
R7 and R8 are the same or different, each represents the group selected from a hydrogen, a halogen, a carboxyl, a linear or cyclic alkyl having 1˜20 carbon atoms, an aryl, alkylaryl, and arylalkyl having 6˜20 carbon atoms; R9 represents a hydrogen atom or an alkyl group having 1-6 carbon atoms);
to produce a polyimide polymer having repeating unit which has acrylic acid group in the main chain, as shown in the above general formula (I).

### Claim 5 (depends on 4)

The process according to claim 4, wherein the diamine having carboxyl and/or hydroxyl functional groups used in step (a) is a diamine having both hydroxyl and carboxyl functional groups.

### Claim 6 (depends on 4)

The process according to claim 4, wherein the diamine having carboxyl and/or hydroxyl functional groups used in step (a) is partially replaced by a diamine having siloxane functional groups.

### Claim 7 (depends on 6)

The process according to claim 6, wherein the diamine having siloxane functional groups comprises 5˜60 mole % of the total diamine.

### Claim 8 (depends on 7)

The process according to claim 7, wherein the diamine having siloxane functional groups is at least one selected from the group consisting of 1,3-di(3-aminopropyl)-1,1,3,3-tetramethyl-disiloxane (DSI), 1,3-di(4-aminobutyl)-1,1,3,3-tetramethyldisiloxane, 1,3-di(3-aminopropyl)-1,3-dimethyl-1,3-diphenyldisiloxane, 1,3-di(3-amino-phenyl)-1,1,3,3-tetramethyldisiloxane, 1,3-di(4-aminophenyl)-1,1,3,3-tetramethyldisiloxane, 1,3-di(3-aminophenoxymethyl)-1,1,3,3-tetramethyldisiloxane, and 1,3-di(4-aminophenoxymethyl)-1,1,3,3-tetramethyldisiloxane.

### Claim 9 (depends on 1)

A water soluble photosensitive polyimide resin composition, which comprised (A) a water soluble photosensitive polyimide polymer having repeat units represented by formula (I) according to claim 1; (B) a (meth)acrylic acid monomer diluent and (C) a photo-initiator; wherein the weight ratio of component (A): component (B) is 100:10˜200, and the amount of component (C) is 0.1˜15.0% relative to 100% by weight of component (A).