# US 11,029,599 B2 · Chemically amplified positive photoresist composition and pattern forming method using same

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- Number: US 11,029,599 B2
- Document ID: US11029599B2
- Status: Granted
- Kind: B2
- Application number: 16/340,413
- Filed: 2017-10-10
- Published: 2019-08-01
- Granted: 2021-06-08
- Earliest claimed: 2016-10-12
- Assignees: Merck Patent GmbH
- Applicants: Ridgefield Acquisition
- Inventors: Tetsumasa Takaichi; Shunji Kawato; Masato Suzuki; Kazumichi Akashi; Tomohide Katayama
- Web page: https://patentgrep.com/patent/US11029599B2

## CPC

- G03F 7/0392: {the macromolecular compound being present in a chemically amplified positive photoresist composition}
- C08F 212/08: Styrene
- C08F 212/12: Monomers containing a branched unsaturated aliphatic radical or a ring substituted by an alkyl radical
- G03F 7/039: Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023)
- G03F 7/162: {Coating on a rotating support, e.g. using a whirler or a spinner}
- G03F 7/168: {Finishing the coated layer, e.g. drying, baking, soaking}
- G03F 7/2004: {characterised by the use of a particular light source, e.g. fluorescent lamps or deep UV light}
- G03F 7/322: {Aqueous alkaline compositions}
- G03F 7/38: Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)}
- G03F 7/40: Treatment after imagewise removal, e.g. baking
- H10P 76/2041: {Photolithographic processes}
- 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)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10

## Abstract

The present invention relates to a photosensitive resin composition suitable for forming a thick film, which comprises (A) an alkali-soluble resin, (B) at least one plasticizer selected from a group consisting of an alkali-soluble vinyl resin and an acid-dissociable group containing vinyl resin, (C) an acid generator, and (D) an organic solvent.

## Claims

### Claim 1

A chemically amplified positive photoresist composition comprising (A) an alkali-soluble resin, (B) at least one plasticizer selected from a group consisting of an alkali-soluble vinyl resin and an acid-dissociable group containing vinyl resin, (C) a photo acid generator, (D) an organic solvent, and (E) a basic compound; wherein the alkali-soluble resin (A), comprises a polymer comprising recurring units represented by a general formula (1), a general formula (2) and a general formula (3) and has a weight average molecular weight of 1,000 to 200,000;
wherein R1 is hydrogen, alkyl or halogen, R2 is hydrogen or alkyl, R3 is C4-C12 tertiary alkyl, m is a positive integer of 1 to 5;
the amount of the plasticizer (B) in the composition is 2-10 parts by mass per 100 parts by mass of the alkali-soluble resin (A);
the amount of the photoacid generator (C) in the composition is 1 to 10 parts by mass per 100 parts by mass of the alkali-soluble resin (A);
the amount of the base (E) in the composition is 0.01-1 parts by mass per 100 parts by mass of the alkali-soluble resin (A); and
the organic solvent (D) is selected from the group consisting of propylene glycol monomethylether arid propylene glycol dimethyl ether mixture, propylene glycol monomethylether and methylisobutylketone mixture, propylene glycol monomethylether and methylethylketone mixture, propylene glycol monomethylether arid n-butyl acetate mixture, propylene glycol monomethylether and cyclopentyl methyl ether mixture, and propylene glycol monomethylether and propyl propionate mixture.

### Claim 2 (depends on 1)

The chemically amplified positive photoresist composition according to claim 1 wherein the alkali-soluble vinyl resin and the acid-dissociable group containing vinyl resin (B) has a weight average molecular weight of 500 to 200,000.

### Claim 3 (depends on 1)

The chemically amplified positive photoresist composition according to claim 1 wherein the alkali-soluble vinyl resin and the acid-dissociable group containing vinyl resin (B) is selected from a polyvinyl ether, a polyvinyl butyral and a polyether ester and mixtures thereof.

### Claim 4 (depends on 1)

The chemically amplified positive photoresist composition according to claim 1 wherein the organic solvent comprising a solvent with viscosity less than 1.0 mPa⋅s at 25° C.

### Claim 5 (depends on 1)

The chemically amplified positive photoresist composition according to claim 1 wherein the polymer comprising recurring units represented by the general formula (1), the general formula (2) and the general formula (3) included in the alkali-soluble resin (A) is a polymer comprising recurring units represented by a formula (4), a formula (5) and a formula (6) and having a weight average molecular weight of 4,000 to 200,000.

### Claim 6 (depends on 1)

The use of a chemically amplified positive photoresist composition according to claim 1 for manufacturing a semiconductor device.

### Claim 7 (depends on 1)

A method for forming a resist pattern, comprising:
a) coating the chemically amplified positive photoresist composition according to claim 1 onto a substrate and prebaking to form a resist film;
b) exposing the resist film to UV radiation having a wavelength of up to 500 nm through a photomask; and
c) optionally baking, and developing with a developer to form a resist pattern.

### Claim 8 (depends on 7)

The method for forming a resist pattern according to claim 7, wherein UV radiation having the wavelength of 248 nm.

### Claim 9 (depends on 7)

A semiconductor device manufacturing method comprising a method for forming a resist pattern according to claim 7.