# US 11,029,598 B2 · Photosensitive polyimide composition and photoresist film made thereof

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- Number: US 11,029,598 B2
- Document ID: US11029598B2
- Status: Granted
- Kind: B2
- Application number: 16/119,464
- Filed: 2018-08-31
- Published: 2019-08-08
- Granted: 2021-06-08
- Earliest claimed: 2018-02-02
- Assignees: eChem Solutions Corp.
- Applicants: eChem Solutions Corp.
- Inventors: Tz Jin Yang; Ming Che Chung
- Web page: https://patentgrep.com/patent/US11029598B2

## CPC

- G03F 7/0233: {characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides}
- C08G 73/1017: {in the form of (mono)amine}
- C08G 73/1039: {comprising halogen-containing substituents}
- C08G 73/1042: {Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds}
- C08G 73/1046: {Polyimides containing oxygen in the form of ether bonds in the main chain}
- C08G 73/105: {with oxygen only in the diamino moiety}
- C08G 73/106: {containing silicon}
- C08G 73/1075: {Partially aromatic polyimides}
- C09D 179/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- G03F 7/0045: {with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors}
- G03F 7/0226: {characterised by the non-macromolecular additives}
- G03F 7/039: Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023)
- G03F 7/0757: {Macromolecular compounds containing Si-O, Si-C or Si-N bonds (G03F7/0752 takes precedence)}
- G03F 7/16: Coating processes; Apparatus therefor (applying coatings to base materials in general B05; applying photosensitive compositions to base for photographic purposes G03C1/74)
- G03F 7/168: {Finishing the coated layer, e.g. drying, baking, soaking}
- G03F 7/20: Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00)
- G03F 7/26: Processing photosensitive materials; Apparatus therefor (G03F7/12 - G03F7/24 take precedence)
- G03F 7/38: Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)}
- 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)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)

## Abstract

The present invention provides a photosensitive polyimide composition comprising a polyimide resin having a structural unit represented by the formula (1) and a structural unit represented by the formula (2), a quinonediazide sulfonate, a thermal curing agent, and a thermal acid generator. In the formulas (1) and (2), n is an integer of 10 to 600, Ar1 is a tetravalent organic group; Ar2 is a divalent to tetravalent organic group; Ar3 is a divalent aromatic group; and R1 is an OH group or a COOH group. The present invention also provides a photoresist film made of the above-mentioned photosensitive polyimide composition.

## Claims

### Claim 1

A photosensitive polyimide composition comprising a polyimide resin having a structural unit represented by the formula (1) and a structural unit represented by the formula (2), an quinonediazide sulfonate, a thermal curing agent, and a thermal acid generator,
wherein in the formulae (1) and (2), n is an integer of 10 to 600, Ar1 is a tetravalent organic group, Ar2 is a divalent to tetravalent organic group, Ar3 is a divalent aromatic group, and R1 is an OH group or a COOH group; the thermal curing agent comprises an epoxy compound and a melamine compound, and the weight ratio of the epoxy compound to the melamine compound is 3:1 to 4:3;
wherein the photoresist film has properties of chemical resistance and insulation, and the property of chemical resistance is expressed by a residual film rate of greater than 90%;
wherein the thermal acid generator is an onium sulfonium salt selected from at least one of the group consisting of chloride, bromide, p-toluenesulfonate, trifluoromethanesulfonate, tetrafluoroborate, tetrakis(pentafluorophenyl)borate, tetrakis(pentafluorophenyl)ruthenate, hexafluorophosphate, hexafluoroarsenate, and hexafluoroantimonate.

### Claim 2 (depends on 1)

The photosensitive polyimide composition according to claim 1, wherein the quinonediazide sulfonate is 10-30 parts by weight relative to 100 parts by weight of the polyimide resin.

### Claim 3 (depends on 1)

The photosensitive polyimide composition according to claim 1, wherein the thermal curing agent is 10 to 50 parts by weight relative to 100 parts by weight of the polyimide resin.

### Claim 4 (depends on 1)

The photosensitive polyimide composition according to claim 1, wherein the thermal acid generator is 1 to 5 parts by weight relative to 100 parts by weight of the polyimide resin.

### Claim 5 (depends on 1)

The photosensitive polyimide composition according to claim 1, wherein the polyimide resin has a structure represented by formula (3),
wherein in formula (3), n is an integer of 10 to 600.

### Claim 6 (depends on 1)

A method of manufacturing a photoresist film, comprising:
applying the photosensitive polyimide composition as described in claim 1 to a substrate;
exposing the photosensitive polyimide composition; and
executing a developing process.

### Claim 7 (depends on 6)

The method for producing a photoresist film according to claim 6, wherein a pre-baking is further performed at 100° C. to 120° C. before exposing the photosensitive polyimide composition.

### Claim 8 (depends on 6)

The method for producing a photoresist film according to claim 6, further comprising a post-baking at 200° C. to 250° C. after the developing process.