# US 8,541,161 B2 · Actinic ray-sensitive or radiation-sensitive resin composition, resist film using the same and pattern forming method

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- Number: US 8,541,161 B2
- Document ID: US8541161B2
- Status: Granted
- Kind: B2
- Application number: 13/257,069
- Filed: 2010-03-23
- Published: 2012-01-05
- Granted: 2013-09-24
- Earliest claimed: 2009-03-26
- Assignees: FUJIFILM Corporation
- Applicants: Kana Fujii; Shuji Hirano; Shinki Yamada; Toru Fujimori
- Inventors: Kana Fujii; Shuji Hirano; Shinki Yamada; Toru Fujimori
- Web page: https://patentgrep.com/patent/US8541161B2

## CPC

- C08F 8/12: Hydrolysis
- C08F 212/22: {Oxygen}
- 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 7/0392: {the macromolecular compound being present in a chemically amplified positive photoresist composition}
- C08F 220/1804: {C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate}
- C08F 220/20: of polyhydric alcohols or phenols {, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate}
- C08K 5/375: containing six-membered aromatic rings {(C08K5/3725 takes precedence)}
- C08K 5/41: Compounds containing sulfur bound to oxygen
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

Provided are an actinic ray-sensitive or radiation-sensitive resin composition; a resist film using the composition; and a pattern forming method. The actinic ray-sensitive or radiation-sensitive resin composition includes (A) a resin capable of increasing the solubility in an alkali developer by the action of an acid, the resin containing a repeating unit represented by formula (I), a repeating unit represented by formula (II) and a repeating unit represented by formula (III), and (B) a compound capable of generating a fluorine atom-containing acid upon irradiation with an actinic ray or radiation: wherein each of R1 and R11 independently represents a hydrogen atom or an alkyl group which may have a substituent, and R12 represents a phenyl group which may have a substituent.

## Claims

### Claim 1

An actinic ray-sensitive or radiation-sensitive resin composition comprising:
(A) a resin capable of increasing the solubility in an alkali developer by the action of an acid, the resin containing a repeating unit represented by formula (I), a repeating unit represented by formula (II) and a repeating unit represented by formula (III),
(B) a compound capable of generating a fluorine atom-containing sulfonic acid upon irradiation with an actinic ray or radiation, and
(B′) a compound capable of generating a fluorine atom-free sulfonic acid upon irradiation with an actinic ray or radiation:
wherein
each of R1 and R11 independently represents a hydrogen atom or an alkyl group which may have a substituent, and
R12 represents a phenyl group which may have a substituent,
wherein the content of the component (B) is from 1.0 to 15 mass %, and the content of the component (B′) is from 0.5 to 3 mass %, based on the entire solids content of the composition.

### Claim 2 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1, wherein
the contents of the repeating unit represented by formula (I), the repeating unit represented by formula (II) and the repeating unit represented by formula (III) are from 50 to 80 mol %, from 15 to 49 mol % and from 0.5 to 10 mol %, respectively, based on all repeating units of the resin (A).

### Claim 3 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1, wherein
the contents of the repeating unit represented by formula (I), the repeating unit represented by formula (II) and the repeating unit represented by formula (III) are from 60 to 75 mol %, from 20 to 39 mol % and from 1 to 9 mol %, respectively, based on all repeating units of the resin (A).

### Claim 4 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1, wherein
each of R1 in formula (II) and R11 in formula (III) is a methyl group.

### Claim 5 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1, wherein
R12 in formula (III) is a phenyl group.

### Claim 6 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1, further comprising:
(D) a compound having three or more hydroxyl or substituted hydroxyl groups.

### Claim 7 (depends on 6)

The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 6, wherein
the compound (D) is a cyclic or chain sugar derivative.

### Claim 8 (depends on 1)

A resist film formed of the actinic ray-sensitive or radiation-sensitive resin composition claimed in claim 1.

### Claim 9 (depends on 8)

A pattern forming method comprising steps of exposing and developing the resist film claimed in claim 8.

### Claim 10 (depends on 1)

The actinic ray-sensitive or radiation-sensitive resin composition as claimed in claim 1, wherein
the component (B) is a sulfonium salt or an iodonium salt, and the component (B′) is a sulfonium salt or an iodonium salt.