# US 12,111,574 B2 · Resist composition, method of forming resist pattern, compound, and resin

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- Number: US 12,111,574 B2
- Document ID: US12111574B2
- Status: Granted
- Kind: B2
- Application number: 17/547,044
- Filed: 2021-12-09
- Published: 2022-06-30
- Granted: 2024-10-08
- Earliest claimed: 2020-12-23
- Assignees: Tokyo Ohka Kogyo Co., Ltd.
- Applicants: Tokyo Ohka Kogyo Co., Ltd.
- Inventors: Takuya Ikeda
- Web page: https://patentgrep.com/patent/US12111574B2

## CPC

- G03F 7/039: Macromolecular compounds which are photodegradable, e.g. positive electron resists (G03F7/075 takes precedence; macromolecular quinonediazides G03F7/023)
- C07C 69/54: Acrylic acid esters; Methacrylic acid esters
- C07D 307/77: ortho- or peri-condensed with carbocyclic rings or ring systems
- C08F 8/12: Hydrolysis
- C08F 12/22: Oxygen
- C08F 212/22: {Oxygen}
- C08F 212/24: {Phenols or alcohols}
- C08F 220/1805: {C5-(meth)acrylate, e.g. pentyl (meth)acrylate}
- C08F 220/1806: {C6-(meth)acrylate, e.g. (cyclo)hexyl (meth)acrylate or phenyl (meth)acrylate}
- 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 220/1811: {C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate}
- C08L 33/14: of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
- C09D 125/18: Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
- G03F 7/0045: {with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors}
- 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 7/0392: {the macromolecular compound being present in a chemically amplified positive photoresist composition}
- G03F 7/0397: {the macromolecular compound having an alicyclic moiety in a side chain}
- G03F 7/322: {Aqueous alkaline compositions}
- G03F 7/325: {Non-aqueous compositions}
- C07C 2601/02: with a three-membered ring
- C07C 2601/04: with a four-membered ring
- C07C 2601/08: the ring being saturated
- C07C 2601/10: the ring being unsaturated
- C07C 2601/14: The ring being saturated
- C07C 2601/16: the ring being unsaturated
- C07C 2602/42: the bicyclo ring system containing seven carbon atoms
- C07C 2603/74: Adamantanes
- C07D 305/06: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
- C07D 307/12: Radicals substituted by oxygen atoms
- C07D 307/33: in position 2, the oxygen atom being in its keto or unsubstituted enol form
- C07D 309/06: Radicals substituted by oxygen atoms
- C07D 309/30: Oxygen atoms, e.g. delta-lactones
- 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)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)

## Abstract

A resist composition containing a polymeric compound having a constitutional unit (a01) derived from a compound represented by General Formula (a0-1). In the formula, W01 represents a polymerizable group-containing group, Ra01 represents a linear or branched hydrocarbon group, and Ra02 and Ra03 each independently represents a hydrocarbon group which may have a substituent

## 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,
wherein the resin component (A1) has a constitutional unit (a01) derived from a compound represented by General Formula (a0-1):
wherein W01 represents a polymerizable group-containing group, Ra01 represents a linear or branched hydrocarbon group, and Ra02 and Ra03 each independently represent a hydrocarbon group which may have a substituent.

### Claim 2 (depends on 1)

The resist composition according to claim 1, further comprising:
an acid generator component (B) which generates acid upon exposure,
wherein the acid generator component (B) contains a compound represented by General Formula (b-1), a compound represented by General Formula (b-2), or a compound represented by General Formula (b-3):
wherein R101 and R104 to R108 each independently represents a cyclic group which may have a substituent, a chain alkyl group which may have a substituent, or a chain alkenyl group which may have a substituent, R104 and R105 may be bonded to each other to form a ring structure, R102 represents a fluorinated alkyl group having 1 to 5 carbon atoms or a fluorine atom, Y101 represents a divalent linking group containing an oxygen atom or a single bond, V101 to V103 each independently represents a single bond, an alkylene group, or a fluorinated alkylene group, L101 and L102 each independently represents a single bond or an oxygen atom, L103 to L1°5 each independently represents a single bond, —CO—, or —SO2—, Mm+ represents an m-valent organic cation, and m represents an integer of 1 or more.

### Claim 3 (depends on 2)

The resist composition according to claim 2, wherein the acid generator component (B) contains a compound represented by General Formula (b-1-0):
wherein R101 represents a cyclic group which may have a substituent, a chain alkyl group which may have a substituent, or a chain alkenyl group which may have a substituent, Yb0 represents a divalent linking group containing an oxygen atom, V101 represents a single bond, an alkylene group, or a fluorinated alkylene group, R102 represents a fluorinated alkyl group having 1 to 5 carbon atoms or a fluorine atom, Mm+ represents an m-valent organic cation, and m represents an integer of 1 or more.

### Claim 4 (depends on 3)

The resist composition according to claim 3, wherein the acid generator component (B) contains a compound represented by General Formula (b-1-1):
wherein R101 represents a cyclic group which may have a substituent, a chain alkyl group which may have a substituent, or a chain alkenyl group which may have a substituent, Yb0 represents a divalent linking group containing an oxygen atom, V101 represents a single bond, an alkylene group, or a fluorinated alkylene group, R102 represents a fluorinated alkyl group having 1 to 5 carbon atoms or a fluorine atom, Rb1 represents an aryl group having a fluorine atom or an aryl group having a fluorinated alkyl group, and Rb2 and Rb3 each independently represents an aryl group which may have a substituent or are bonded to each other to form a ring together with a sulfur atom in the formula.

### Claim 5 (depends on 1)

The resist composition according to claim 1, wherein the constitutional unit (a01) is a constitutional unit represented by General Formula (a01-1):
wherein R01 represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a halogenated alkyl group having 1 to 5 carbon atoms, Va01 represents a divalent linking group, na01 represents an integer in a range of 0 to 2, and Ra001 to Ra003 each independently represents a linear or branched alkyl group.

### Claim 6 (depends on 1)

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

### Claim 7

A compound represented by General Formula (a0-1):
wherein W01 represents a polymerizable group-containing group, Ra01 represents a linear or branched hydrocarbon group, and Ra02 and Ra03 each independently represents a hydrocarbon group which may have a substituent.

### Claim 8

A resin comprising:
a constitutional unit (a01) derived from a compound represented by General Formula (a0-1):
wherein W01 represents a polymerizable group-containing group, Ra01 represents a linear or branched hydrocarbon group, and Ra02 and Ra03 each independently represents a hydrocarbon group which may have a substituent.

### Claim 9 (depends on 1)

The resist composition according to claim 1, wherein the resin component (A1) has a constitutional unit (a01) represented by any one of General Formula (a01-1a-1) to (a01-1a-29):
wherein Rα represents a hydrogen atom, a methyl group, or a trifluoromethyl group.

### Claim 10 (depends on 7)

The compound according to claim 7, which is represented by any one of Chemical Formula (a01-1m-1) to (a01-1m-30):

### Claim 11 (depends on 8)

The resin according to claim 8,
wherein the constitutional unit (a01) is represented by any one of General Formula (a01-1a-1) to (a01-1a-29):
wherein Rα represents a hydrogen atom, a methyl group, or a trifluoromethyl group.