# US 7,611,822 B2 · Salt suitable for an acid generator and a chemically amplified positive resist composition containing the same

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 7,611,822 B2
- Document ID: US7611822B2
- Status: Granted
- Kind: B2
- Application number: 12/219,453
- Filed: 2008-07-22
- Published: 2009-02-12
- Granted: 2009-11-03
- Earliest claimed: 2007-07-25
- Assignees: Sumitomo Chemical Company, Limited
- Inventors: Ichiki Takemoto
- Web page: https://patentgrep.com/patent/US7611822B2

## CPC

- C07C 381/12: Sulfonium compounds
- C07C 309/10: with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom
- C07C 309/12: containing esterified hydroxy groups bound to the carbon skeleton
- C07D 317/72: spiro-condensed with carbocyclic rings
- C07D 333/46: substituted on the ring sulfur atom
- G03F 7/0045: {with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors}
- G03F 7/0397: {the macromolecular compound having an alicyclic moiety in a side chain}
- C07C 2603/74: Adamantanes
- Y10S 430/106: Binder containing
- Y10S 430/108: Polyolefin or halogen containing
- Y10S 430/111: Polymer of unsaturated acid or ester
- Y10S 430/122: Sulfur compound containing
- Y10S 430/123: Sulfur in heterocyclic ring
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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)
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

The present invention provides a salt represented by the formula (I): wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, T represents a methylene group or a carbonyl group, R represents an adamantyl group substituted with at least one selected from the group consisting of a C1-C4 alkyl group, a C1-C4 alkoxy group, a hydroxyl group, a hydroxymethyl group, a cyano group and an oxo group, and A+ represents an organic counter ion. The present invention further provides a chemically amplified resist composition comprising the salt represented by the above-mentioned formula (I).

## Claims

### Claim 1

A salt represented by the formula (I):
wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, T represents a methylene group or a carbonyl group, R represents an adamantyl group substituted with at least one selected from the group consisting of a C1-C4 alkyl group, a C1-C4 alkoxy group, a hydroxyl group, a hydroxymethyl group, a cyano group and an oxo group, and A+ represents an organic counter ion.

### Claim 2 (depends on 1)

The salt according to claim 1, wherein Q1 and Q2 each independently represent a fluorine atom or a trifluoromethyl group.

### Claim 3 (depends on 1)

The salt according to claim 1, wherein Q1 and Q2 represent fluorine atoms.

### Claim 4 (depends on 1)

The salt according to claim 1, wherein the organic counter ion is at least one cation selected from the group consisting of a cation represented by the formula (IIa):
wherein P1, P2 and P3 each independently represent a hydrogen atom, a hydroxyl group, a C1-C12 alkyl group or a C1-C12 alkoxy group, a cation represented by the formula (IIb):
wherein P4 and P5 each independently represent a hydrogen atom, a hydroxyl group, a C1-C12 alkyl group or a C1-C12 alkoxy group, a cation represented by the formula (IIc):
wherein P6 and P7 each independently represent a C1-C12 alkyl group or a C3-C12 cycloalkyl group, or P6 and P7 are bonded to form a C3-C12 divalent acyclic hydrocarbon group which forms a ring together with the adjacent S+, and at least one —CH2— in the divalent acyclic hydrocarbon group may be substituted with —CO—, —O— or —S—,
P8 represents a hydrogen atom, P9 represents a C1-C12 alkyl group, a C3-C12 cycloalkyl group or an aromatic group which may be substituted, or P8 and P9 are bonded to form a divalent acyclic hydrocarbon group which forms a 2-oxocycloalkyl group together with the adjacent —CHCO—, and at least one —CH2— in the divalent acyclic hydrocarbon group may be substituted with —CO—, —O— or —S—, and a cation represented by the formula (IId):
wherein P10, P11, P12, P13, P14, P15, P16, P17, P18, P19, P20 and P21 each independently represent a hydrogen atom, a hydroxyl group, a C1-C12 alkyl group or a C1-C12 alkoxy group, B represents a sulfur or oxygen atom and k represents 0 or 1.

### Claim 5 (depends on 1)

The salt according to claim 1, wherein the organic counter ion is a cation represented by the formula (IIa).

### Claim 6 (depends on 5)

The salt according to claim 5, wherein the cation represented by the formula (IIa) is a cation represented by the formula (IIe):
wherein P22, P23 and P24 each independently represent a hydrogen atom or C1-C4 alkyl group.

### Claim 7 (depends on 1)

The salt according to claim 1, wherein R represents an adamantyl group substituted with a hydroxyl group or an oxo group.

### Claim 8 (depends on 7)

The salt according to claim 7, wherein the organic counter ion is a cation represented by the formula (IIe):
wherein P22, P23 and P24 each independently represent a hydrogen atom or C1-C4 alkyl group.

### Claim 9

A chemically amplified positive resist composition comprising a salt represented by the formula (I):
wherein Q1 and Q2 each independently represent a fluorine atom or a C1-C6 perfluoroalkyl group, T represents a methylene group or a carbonyl group, R represents an adamantyl group substituted with at least one selected from the group consisting of a C1-C4 alkyl group, a C1-C4 alkoxy group, a hydroxyl group, a hydroxymethyl group, a cyano group and an oxo group, and A+ represents an organic counter ion, and a resin which contains a structural unit which has an acid-labile group and which itself is insoluble or poorly soluble in an aqueous alkali solution but becomes soluble in an aqueous alkali solution by the action of an acid.

### Claim 10 (depends on 9)

The chemically amplified positive resist composition according to claim 9, wherein Q1 and Q2 each independently represent a fluorine atom or a trifluoromethyl group.

### Claim 11 (depends on 9)

The chemically amplified positive resist composition according to claim 9, wherein Q1 and Q2 represent fluorine atoms.

### Claim 12 (depends on 9)

The chemically amplified positive resist composition according to claim 9, wherein the resin contains a structural unit derived from a monomer having a bulky and acid-labile group.

### Claim 13 (depends on 12)

The chemically amplified positive resist composition according to claim 12, wherein the bulky and acid-labile group is a 2-alkyl-2-adamantyl ester group or a 1-(1-adamantyl)-1-alkylalkyl ester group.

### Claim 14 (depends on 12)

The chemically amplified positive resist composition according to claim 12, wherein the monomer having a bulky and acid-labile group is 2-alkyl-2-adamantyl acrylate, 2-alkyl-2-adamantylmethacrylate, 1-(1-adamantyl)-1-alkylalkyl acrylate, 1-(1-adamantyl)-1-alkylalkyl methacrylate, 2-alkyl-2-adamantyl 5-norbornene-2-carboxylate, 1-(1-adamantyl)-1-alkylalkyl 5-norbornene-2-carboxylate, 2-alkyl-2-adamantyl α-chloroacrylate or 1-(1-adamantyl)-1-alkylalkyl α-chloroacrylate.

### Claim 15 (depends on 12)

The chemically amplified positive resist composition according to claim 12, wherein the monomer having a bulky and acid-labile group is 2-alkyl-2-adamantylacrylate, 2-alkyl-2-adamantyl methacrylate, 1-(1-adamantyl)-1-alkylalkylacrylate and 1-(1-adamantyl)-1-alkylalkyl methacrylate.

### Claim 16 (depends on 12)

The chemically amplified positive resist composition according to claim 12, wherein the monomer having a bulky and acid-labile group is 2-alkyl-2-adamantyl acrylate and 2-alkyl-2-adamantyl methacrylate.

### Claim 17 (depends on 9)

The chemically amplified positive resist composition according to claim 9, wherein the chemically amplified positive resist composition further comprises a basic compound.