# US 2018/0321585 A1 · Radiation-sensitive resin composition, resist pattern-forming method and acid diffusion control agent

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- Number: US 2018/0321585 A1
- Document ID: US20180321585A1
- Status: Published application
- Kind: A1
- Application number: 16/030,227
- Filed: 2018-07-09
- Published: 2018-11-08
- Earliest claimed: 2016-01-13
- Assignees: Jsr Corporation
- Applicants: JSR Corporation
- Inventors: Natsuko KINOSHITA
- Web page: https://patentgrep.com/patent/US20180321585A1

## CPC

- G03F 7/0045: {with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors}
- C07D 233/64: with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- C07D 235/02: condensed with carbocyclic rings or ring systems
- C07D 235/18: with aryl radicals directly attached in position 2
- C08F 2/48: by ultraviolet or visible light
- C08F 220/16: of phenols or of alcohols containing two or more carbon atoms
- C08F 220/1807: {C7-(meth)acrylate, e.g. heptyl (meth)acrylate or benzyl (meth)acrylate}
- C08F 220/1808: {C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate}
- C08F 220/1809: {C9-(meth)acrylate}
- C08F 220/1818: {C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate}
- C08F 220/28: containing no aromatic rings in the alcohol moiety
- C08F 220/283: {and containing one or more carboxylic moiety in the chain, e.g. acetoacetoxyethyl(meth)acrylate}
- G03F 7/038: Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021)
- G03F 7/039: Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023)
- G03F 7/0397: {the macromolecular compound having an alicyclic moiety in a side chain}
- 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 7/30: Imagewise removal using liquid means
- G03F 7/322: {Aqueous alkaline compositions}
- G03F 7/38: Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)}
- C08F 220/1806: {C6-(meth)acrylate, e.g. (cyclo)hexyl (meth)acrylate or phenyl (meth)acrylate}
- C08F 220/1811: {C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate}
- C08F 220/1812: {C12-(meth)acrylate, e.g. lauryl (meth)acrylate}
- C08F 220/22: Esters containing halogen
- C08F 220/281: {and containing only one oxygen, e.g. furfuryl (meth)acrylate or 2-methoxyethyl (meth)acrylate}
- C08F 2800/10: as molar percentages
- 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)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

A radiation-sensitive resin composition includes: a first polymer having a first structural unit that includes an acid-labile group; a radiation-sensitive acid generator; and a first compound capable of forming a salt through a structural change in a molecule thereof upon irradiation with a radioactive ray. Basicity of the first compound preferably changes upon irradiation with a radioactive ray. The first compound preferably generates an acid upon irradiation with a radioactive ray. The first compound is preferably represented by formula (1). In formula (1), Ar1 represents a substituted or unsubstituted heteroarenediyl group having 4 to 30 ring atoms and having at least one nitrogen atom as a ring-constituting atom.

## Claims

### Claim 1

A radiation-sensitive resin composition comprising:
a first polymer comprising a first structural unit that comprises an acid-labile group;
a radiation-sensitive acid generator; and
a first compound capable of forming a salt through a structural change in a molecule thereof upon irradiation with a radioactive ray, the first compound not being a salt.

### Claim 2 (depends on 1)

The radiation-sensitive resin composition according to claim 1, wherein basicity of the first compound changes upon irradiation with a radioactive ray.

### Claim 3 (depends on 1)

The radiation-sensitive resin composition according to claim 1, wherein the first compound generates an acid upon irradiation with a radioactive ray.

### Claim 4 (depends on 1)

The radiation-sensitive resin composition according to claim 1, wherein the first compound is represented by formula (1):
wherein, in the formula (1), Ar1 represents a substituted or unsubstituted heteroarenediyl group having 4 to 30 ring atoms and having at least one nitrogen atom as a ring-constituting atom; Ar2 represents a substituted or unsubstituted aryl group having 6 to 30 ring atoms in which at least one hydrogen atom bonds to a carbon atom of an aromatic ring, or a substituted or unsubstituted heteroaryl group having 4 to 30 ring atoms in which at least one hydrogen atom bonds to a carbon atom of an aromatic ring; Ar3 represents an aryl group having 6 to 30 ring atoms in which at least one leaving group bonds to a carbon atom of an aromatic ring and having or not having a substituent other than the leaving group, or a heteroaryl group having 4 to 30 ring atoms in which at least one leaving group bonds to a carbon atom of an aromatic ring and having or not having a substituent other than the leaving group, wherein number of covalent bonds constituting a shortest bond path between the carbon atom to which the hydrogen atom bonds in Ar2 and the carbon atom to which the leaving group bonds in Ar3 is no less than 4 and no greater than 7.

### Claim 5 (depends on 4)

The radiation-sensitive resin composition according to claim 4, wherein the compound represented by the formula (1) is represented by formula (1-1):
wherein, in the formula (1-1), R1 and R2 each independently represent a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, or R1 and R2 taken together represent a ring structure having 4 to 20 ring atoms together with the carbon atom to which R1 and R2 bond; R3 represents a monovalent organic group having 1 to 20 carbon atoms; n is an integer of 0 to 4, wherein in a case in which n is no less than 2, a plurality of R3s are identical or different, and the plurality of R3s optionally taken together represent a ring structure having 4 to 20 ring atoms together with the carbon chain to the which the plurality of R3s bond; R4 represents a monovalent organic group having 1 to 20 carbon atoms other than a leaving group; m is an integer of 0 to 4, wherein in a case in which m is no less than 2, a plurality of R4s are identical or different, and the plurality of R4s optionally taken together represent a ring structure having 4 to 20 ring atoms together with the carbon chain to which the plurality of R4s bond; and X represents a monovalent leaving group.

### Claim 6 (depends on 1)

The radiation-sensitive resin composition according to claim 1, wherein the first structural unit is a structural unit represented by formula (2), a structural unit that comprises an acetal structure or a combination thereof,
wherein, in the formula (2), R5 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group; R6 represents a monovalent hydrocarbon group having 1 to 20 carbon atoms; and R7 and R8 each independently represent a monovalent hydrocarbon group having 1 to 20 carbon atoms, or R7 and R8 taken together represent an alicyclic structure having 3 to 20 ring atoms together with the carbon atom to which R7 and R8 bond.

### Claim 7 (depends on 1)

A resist pattern-forming method comprising:
applying the radiation-sensitive resin composition according to claim 1 on one face side of a substrate;
exposing the resist film obtained after the applying; and
developing the resist film exposed.

### Claim 8

An acid diffusion control agent comprising a compound capable of forming a salt through a structural change in a molecule thereof upon irradiation with a radioactive ray, the compound not being a salt.