# US 9,519,214 B2 · Actinic-ray- or radiation-sensitive resin composition, actinic-ray- or radiation-sensitive film, pattern forming method, process for manufacturing electronic device and electronic device

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- Number: US 9,519,214 B2
- Document ID: US9519214B2
- Status: Granted
- Kind: B2
- Application number: 14/818,310
- Filed: 2015-08-05
- Published: 2015-11-26
- Granted: 2016-12-13
- Earliest claimed: 2013-02-05
- Assignees: FUJIFILM Corporation
- Applicants: FUJIFILM Corporation
- Inventors: Fumihiro Yoshino
- Web page: https://patentgrep.com/patent/US9519214B2

## CPC

- 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 7/0397: {the macromolecular compound having an alicyclic moiety in a side chain}
- G03F 7/0758: {with silicon- containing groups in the side chains}
- G03F 7/11: having cover layers or intermediate layers, e.g. subbing layers {(G03F7/091 - G03F7/093, B41N3/03 take precedence)}
- G03F 7/20: Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00)
- G03F 7/2041: {in the presence of a fluid, e.g. immersion; using fluid cooling means}
- G03F 7/30: Imagewise removal using liquid means
- G03F 7/322: {Aqueous alkaline compositions}
- G03F 7/325: {Non-aqueous compositions}
- 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

An actinic-ray- or radiation-sensitive resin composition includes a compound (A) that is configured to produce an acid when exposed to actinic rays or radiation, and a resin (B). The compound (A) is expressed by general formula (1) or (2) below. The resin (B) contains a repeating unit (b) containing a group that is configured to decompose when acted on by an acid to thereby produce an alcoholic hydroxyl group.

## Claims

### Claim 1

An actinic-ray- or radiation-sensitive resin composition comprising a compound (A) that is configured to produce an acid when exposed to actinic rays or radiation, the compound expressed by general formula (1) or (2) below, and a resin (B) containing a repeating unit (b) containing a group that is configured to decompose when acted on by an acid to thereby produce an alcoholic hydroxyl group,
in general formula (1),
R1A represents a linear, branched-chain or cyclic organic group;
each of R2A and R3A independently represents a hydrogen atom, a methyl group or CF3;
R4A represents a hydrogen atom, a hydroxyl group, a linear or branched-chain alkyl group, a cycloalkyl group, a linear, branched-chain or cyclic alkyloxy group or any of groups of general formula (1a) below, provided that a fluorine atom may be contained in each of the alkyl group and the alkyloxy group; and
XA represents an alkylene chain in which a heteroatom may be contained, the alkylene chain constructing a ring in cooperation with the S atom in the formula, and
in general formula (2),
R1B represents a linear, branched-chain or cyclic organic group;
R4B represents a hydrogen atom, a hydroxyl group, a linear or branched-chain alkyl group, a cycloalkyl group, a linear, branched-chain or cyclic alkyloxy group or any of groups of general formula (1a) below, provided that a fluorine atom may be contained in each of the alkyl group and the alkyloxy group;
XB represents an alkylene chain in which a heteroatom may be contained, the alkylene chain constructing a ring in cooperation with the S atom in the formula; and
nB is 0 or 1,
in general formula (1a),
n is an integer of 1 or greater; and
* represents a site of bonding to the naphthyl group in general formula (1) or (2).

### Claim 2 (depends on 1)

The actinic-ray- or radiation-sensitive resin composition according to claim 1, wherein R4A in general formula (1), or R4B in general formula (2), is any of groups of general formula (3a) or (3b) below,
in general formula (3a),
R represents a linear or branched-chain fluoroalkyl group having 1 to 4 carbon atoms in which at least one fluorine atom is introduced; and
* represents a site of bonding to the naphthyl group in general formula (1) or (2), and
in general formula (3b),
m is an integer of 1 to 4; and
* represents a site of bonding to the naphthyl group in general formula (1) or (2).

### Claim 3 (depends on 1)

The actinic-ray- or radiation-sensitive resin composition according to claim 1, wherein the resin (B) contains at least any of structures of general formula (OR-1) below as the group that is configured to decompose when acted on by an acid to thereby produce an alcoholic hydroxyl group,
in which
each of Rx1s independently represents a hydrogen atom or a monovalent organic group, provided that two Rx1s may be bonded to each other to thereby form a ring;
Rx2 represents a monovalent organic group, provided that one of Rx1s and Rx2 may be bonded to each other to thereby form a ring; and
* represents a site of bonding to residue of repeating unit (b).

### Claim 4 (depends on 1)

The actinic-ray- or radiation-sensitive resin composition according to claim 1, further comprising any of nitrogen-containing compounds (C) of general formula (5) below,
in which
R9 represents a hydrogen atom or an organic group that is configured to decompose when acted on by an acid, and
R10 represents a hydrogen atom, an alkyl group or an aryl group.

### Claim 5 (depends on 1)

The actinic-ray- or radiation-sensitive resin composition according to claim 1, further comprising (D) any of compounds of general formula (6a) or (6b) below, or any of salts of the compounds,
in general formula (6a), Ra represents an organic group, provided that one in which a carbon atom directly bonded to the carboxylic acid group in the formula is substituted with a fluorine atom is excluded, and
in general formula (6b), Rb represents an organic group, provided that one in which a carbon atom directly bonded to the sulfonic acid group in the formula is substituted with a fluorine atom is excluded.

### Claim 6 (depends on 1)

The actinic-ray- or radiation-sensitive resin composition according to claim 1, further comprising a hydrophobic resin (HR) containing a fluorine atom or a silicon atom.

### Claim 7 (depends on 6)

The actinic-ray- or radiation-sensitive resin composition according to claim 6, wherein the hydrophobic resin (HR) contains a repeating unit containing a basic group or a group whose basicity is increased when acted on by an acid.

### Claim 8 (depends on 1)

The actinic-ray- or radiation-sensitive resin composition according to claim 1, further comprising a solvent containing a compound (G) expressed by formula (7) below, in which the compound (G) is contained in an amount of 10% or less based on the whole mass of the solvent

### Claim 9 (depends on 1)

An actinic-ray- or radiation-sensitive film formed from the actinic-ray- or radiation-sensitive resin composition of claim 1.

### Claim 10 (depends on 1)

A method of forming a pattern, comprising forming the actinic-ray- or radiation-sensitive resin composition of claim 1 into an actinic-ray- or radiation-sensitive film, exposing the actinic-ray- or radiation-sensitive film to actinic rays or radiation, and developing the exposed actinic-ray- or radiation-sensitive film.

### Claim 11 (depends on 10)

The pattern forming method according to claim 10, wherein the development is performed with a developer comprising an organic solvent.

### Claim 12 (depends on 10)

A process for manufacturing an electronic device, comprising the pattern forming method according to claim 10.

### Claim 13 (depends on 1)

The actinic-ray- or radiation-sensitive resin composition according to claim 1, wherein R4A in general formula (1) represents a hydrogen atom, a hydroxyl group, a linear or branched-chain alkyl group, a cycloalkyl group, a branched-chain or cyclic alkyloxy group, a group of general formula (3a) below, or a group of general formula (1a), provided that a fluorine atom may be contained in each of the alkyl group and the alkyloxy group, and
*—O—R (3a)
in general formula (3a), R represents a linear fluoroalkyl group having 1 to 4 carbon atoms in which at least one fluorine atom is introduced, and * represents a site of bonding to the naphthyl group in general formula (1).

### Claim 14 (depends on 1)

The actinic-ray- or radiation-sensitive resin composition according to claim 1, wherein each of R2A and R3A represents a hydrogen atom.