# US 11,029,600 B2 · Resist composition and method of forming resist pattern

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- Number: US 11,029,600 B2
- Document ID: US11029600B2
- Status: Granted
- Kind: B2
- Application number: 16/535,647
- Filed: 2019-08-08
- Published: 2020-03-12
- Granted: 2021-06-08
- Earliest claimed: 2018-09-07
- Assignees: Tokyo Ohka Kogyo Co., Ltd.
- Applicants: Tokyo Ohka Kogyo Co., Ltd.
- Inventors: Takehito Seo; Tomoyuki Hirano; Yuta Iwasawa; Yusuke Itagaki
- Web page: https://patentgrep.com/patent/US11029600B2

## CPC

- G03F 7/0392: {the macromolecular compound being present in a chemically amplified positive photoresist composition}
- C08F 220/16: of phenols or of alcohols containing two or more carbon atoms
- C08F 220/18: with acrylic or methacrylic acids
- C08F 220/28: containing no aromatic rings in the alcohol moiety
- C08F 220/36: containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate}
- G03F 7/0045: {with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors}
- G03F 7/0046: {with perfluoro compounds, e.g. for dry lithography (G03F7/0048 takes precedence)}
- G03F 7/0382: {the macromolecular compound being present in a chemically amplified negative photoresist composition}
- G03F 7/0397: {the macromolecular compound having an alicyclic moiety in a side chain}
- C08F 220/283: {and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate}
- C08F 220/365: {containing further carboxylic moieties}
- 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 7/2006: {using coherent light; using polarised light}
- G03F 7/2041: {in the presence of a fluid, e.g. immersion; using fluid cooling means}
- G03F 7/322: {Aqueous alkaline compositions}
- 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)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

A resist composition including a resin component having more than 30 mol % of a structural unit represented by formula (a0-1), and an acid generator represented by formula (b1) in which R01 represents a hydrogen atom, an alkyl group or a halogenated alkyl group; Va01 represents an alkylene group; Ra01 represents an acid dissociable group; Rb01 represents an cyclic hydrocarbon group; Lb01 represents —O—C(═O)— or —C(═O)—O—; Yb01 represents a divalent linking group or a single bond; Vb01 represents a fluorinated alkylene group; Rb02 represents a fluorine atom or a hydrogen atom; provided that the total number of fluorine atoms contained in Vb01 and Rb02 is 2 or 3; and Mm+ represents an m-valent organic cation.

## Claims

### Claim 1

A resist composition which generates acid upon exposure and exhibits changed solubility in a developing solution under action of acid, the resist composition comprising:
a resin component (A1) which exhibits changed solubility in a developing solution under action of acid, and
an acid-generator component (B) which generates acid upon exposure,
the resin component (A1) comprising a structural unit (a0) represented by general formula (a0-1) shown below,
the amount of the structural unit (a0) based on the combined total (100 mol %) of all structural units constituting the resin component (A1) being more than 30 mol %, and
the acid-generator component (B) comprising an acid generator (B1) represented by general formula (b1) shown below:
wherein, in formula (a0-1), R01 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; Va01 represents an alkylene group having 1 to 10 carbon atoms; Ra01 represents an acid dissociable group; in formula (b1), Rb01 represents a cyclic hydrocarbon group of 3 to 20 carbon atoms which may have a substituent; Lb01 represents —O—C(═O)— or —C(═O)—O—; Yb01 represents a divalent linking group or a single bond; Vb01 represents a fluorinated alkylene group having 1 to 9 carbon atoms; Rb02 represents a fluorine atom or a hydrogen atom; provided that the total number of fluorine atoms contained in Vb01 and Rb02 is 2 or 3; m represents an integer of 1 or more; and Mm+ represents an m-valent organic cation.

### Claim 2 (depends on 1)

The resist composition according to claim 1, wherein the resin component (A1) further comprises a structural unit (a1) containing an acid decomposable group that exhibits increased polarity by the action of acid, provided that the structural unit (a0) is excluded from the structural unit (a1).

### Claim 3 (depends on 2)

The resist composition according to claim 2, wherein the amount of the structural unit (a0) based on the total amount (100 mol %) of the structural unit (a0) and the structural unit (a1) is 50 mol % or more.

### Claim 4 (depends on 2)

The resist composition according to claim 2, wherein the structural unit (a1) comprises a structural unit represented by general formula (a1-11) shown below:
wherein R11 represents a hydrogen atom, an alkyl group of 1 to 5 carbon atoms or a halogenated alkyl group of 1 to 5 carbon atoms; and Ra11 represents an acid dissociable group.

### Claim 5 (depends on 4)

The resist composition according to claim 4, wherein both Ra01 in general formula (a0-1) and Ra11 in general formula (a1-11) is an acid dissociable group which is a cyclic aliphatic hydrocarbon group having a tertiary carbon atom bonded to the oxygen atom (—O—) in the formulae.

### Claim 6 (depends on 1)

The resist composition according to claim 1, wherein the amount of the acid-generator component (B1) relative to 100 parts by weight of the resin component (A1) is 5 to 20 parts by weight.

### Claim 7 (depends on 1)

A method of forming a resist pattern, comprising:
forming a resist film with the resist composition according to claim 1;
exposing the resist film; and
developing the exposed resist film to form a resist pattern.

### Claim 8 (depends on 7)

The method according to claim 7, wherein the resist film is exposed to immersion lithography.