# US 2021/0341836 A1 · Salt, acid generator, resist composition and method for producing resist pattern

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- Number: US 2021/0341836 A1
- Document ID: US20210341836A1
- Status: Published application
- Kind: A1
- Application number: 17/232,459
- Filed: 2021-04-16
- Published: 2021-11-04
- Earliest claimed: 2020-04-22
- Assignees: Sumitomo Chemical Company, Limited
- Applicants: Sumitomo Chemical Company, Limited
- Inventors: Katsuhiro KOMURO; Takashi NAKAKOJI; Koji ICHIKAWA
- Web page: https://patentgrep.com/patent/US20210341836A1

## CPC

- G03F 7/0045: {with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors}
- C07C 309/12: containing esterified hydroxy groups bound to the carbon skeleton
- C07C 309/17: containing carboxyl groups bound to the carbon skeleton
- C07C 323/20: with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C 381/12: Sulfonium compounds
- C07D 307/77: ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D 321/10: condensed with carbocyclic rings or ring systems
- 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 7/38: Treatment before imagewise removal, e.g. prebaking {(G03F7/265 takes precedence)}
- C07C 2603/74: Adamantanes
- H10P 76/2041: {Photolithographic processes}
- 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)
- H10P: GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10

## Abstract

A salt represented by formula (I), an acid generator and a resist composition: wherein R1, R2 and R3 each represent a hydroxy group, —O—R10, —O—CO—O—R10 or —O-L1-CO—O—R10, L1 represents an alkanediyl group, R4, R5, R6, R7, R8 and R9 each represent a halogen atom, an alkyl fluoride group or a hydrocarbon group, R10 represents an acid-labile group, X1, X2 and X3 each independently represent an oxygen atom or a sulfur atom, m1 is an integer of 1 to 5, m2, m3, m8 and m9 represent an integer of 0 to 5, m4, m5, m6 and m7 represent an integer of 0 to 4, in which 1≤m1+m7≤5, 0≤m2+m8≤5, 0≤m3+m9≤5, and AI− represents an organic anion.

## Claims

### Claim 1

A salt represented by formula (I):
wherein, in formula (I),
R1, R2 and R3 each independently represent a hydroxy group, —O—R10, —O—CO—O—R10 or —O-L1-CO—O—R10,
L1 represents an alkanediyl group having 1 to 6 carbon atoms,
R4, R5, R6, R7, R8 and R9 each independently represent a halogen atom, an alkyl fluoride group having 1 to 12 carbon atoms or a hydrocarbon group having 1 to 18 carbon atoms, the hydrocarbon group may have a substituent, and —CH2— included in the hydrocarbon group may be replaced by —O—, —CO—, —S— or —SO2—,
R10 represents an acid-labile group,
X1, X2 and X3 each independently represent an oxygen atom or a sulfur atom,
m1 represents an integer of 1 to 5, and when m1 is 2 or more, a plurality of groups in parentheses may be the same or different from each other,
m2 represents an integer of 0 to 5, and when m2 is 2 or more, a plurality of groups in parentheses may be the same or different from each other,
m3 represents an integer of 0 to 5, and when m3 is 2 or more, a plurality of groups in parentheses may be the same or different from each other, and when m2 or m3 is 1 or more, and R1, R2 and R3 each independently represent —O—R10, —O—CO—O—R10 or —O-L1-CO—O—R10, a plurality of R10 may be the same or different from each other,
m4 represents an integer of 0 to 4, and when m4 is 2 or more, a plurality of R4 may be the same or different from each other,
m5 represents an integer of 0 to 4, and when m5 is 2 or more, a plurality of R5 may be the same or different from each other,
m6 represents an integer of 0 to 4, and when m6 is 2 or more, a plurality of R6 may be the same or different from each other,
m7 represents an integer of 0 to 4, and when m7 is 2 or more, a plurality of R7 may be the same or different from each other,
m8 represents an integer of 0 to 5, and when m8 is 2 or more, a plurality of R8 may be the same or different from each other,
m9 represents an integer of 0 to 5, and when m9 is 2 or more, a plurality of R9 may be the same or different from each other,
in which 1≤m1+m7≤5, 0≤m2+m8≤5, 0≤m3+m9≤5, and
AI− represents an organic anion.

### Claim 2 (depends on 1)

The salt according to claim 1, wherein X1, X2 and X3 are an oxygen atom.

### Claim 3 (depends on 1)

The salt according to claim 1, wherein R1, R2 and R3 each independently represent —O—R10, —O—CO—O—R10 or —O-L1-CO—O—R10.

### Claim 4 (depends on 1)

The salt according to claim 1, wherein the acid-labile group as for R10 is a group represented by formula (1a) or a group represented by formula (2a):
wherein, in formula (1a), Raa1, Raa2 and Raa3 each independently represent an alkyl group having 1 to 8 carbon atoms which may have a substituent, an alkenyl group having 2 to 8 carbon atoms which may have a substituent, an alicyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, or Raa1 and Raa2 are bonded to each other to form an alicyclic hydrocarbon group having 3 to 20 carbon atoms together with carbon atoms to which Raa1 and Raa2 are bonded, and
* represents a bond:
wherein, in formula (2a), Raa1′ and Raa2′ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, Raa3′ represents a hydrocarbon group having 1 to 20 carbon atoms, or Raa2′ and Raa3′ are bonded to each other to form a heterocyclic group having 3 to 20 carbon atoms together with —C—Xa— to which Raa2′ and Raa3′ are bonded, and —CH2— included in the hydrocarbon group and the heterocyclic group may be replaced by —O— or —S—,
Xa represents an oxygen atom or a sulfur atom, and
* represents a bond.

### Claim 5 (depends on 4)

The salt according to claim 4, wherein the acid-labile group as for R10 is a group represented by formula (1a).

### Claim 6 (depends on 4)

The salt according to claim 4, wherein the acid-labile group as for R10 is a group represented by formula (2a).

### Claim 7 (depends on 1)

The salt according to claim 1, wherein either m8 or m9 is an integer of 1 or more, and
R8 and R9 each independently represent a fluorine atom, an iodine atom or a trifluoromethyl group.

### Claim 8 (depends on 1)

The salt according to claim 1, wherein AI− is a sulfonic acid anion, a sulfonylimide anion, a sulfonylmethide anion or a carboxylic acid anion.

### Claim 9 (depends on 1)

The salt according to claim 1, wherein AI− is a sulfonic acid anion and the sulfonic acid anion is an anion represented by formula (I-A):
wherein, in formula (I-A),
Q1 and Q2 each independently represent a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms,
L1 represents a saturated hydrocarbon group having 1 to 24 carbon atoms, —CH2— included in the saturated hydrocarbon group may be replaced by —O— or —CO—, and a hydrogen atom included in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group, and
Y1 represents a methyl group which may have a substituent or an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and —CH2— included in the alicyclic hydrocarbon group may be replaced by —O—, —SO2— or —CO—.

### Claim 10 (depends on 1)

An acid generator comprising the salt according to claim 1.

### Claim 11 (depends on 10)

A resist composition comprising the acid generator according to claim 10 and a resin having an acid-labile group.

### Claim 12 (depends on 11)

The resist composition according to claim 11, wherein the resin having an acid-labile group is at least one selected from the group consisting of a structural unit represented by formula (a1-1) and a structural unit represented by formula (a1-2):
wherein, in formula (a1-1) and formula (a1-2),
La1 and La2 each independently represent —O— or *—O—(CH2)k1—CO—O—, k1 represents an integer of 1 to 7, and * represents a bond to —CO—,
Ra4 and Ra5 each independently represent a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom,
Ra6 and Ra7 each independently represent an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group obtained by combining these groups,
m1 represents an integer of 0 to 14,
n1 represents an integer of 0 to 10, and
n1′ represents an integer of 0 to 3.

### Claim 13 (depends on 11)

The resist composition according to claim 11, wherein the resin having an acid-labile group includes a structural unit represented by formula (a2-A):
wherein, in formula (a2-A),
Ra50 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom,
Ra51 represents a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group or a methacryloyloxy group,
Aa50 represents a single bond or *—Xa51-(Aa52-Xa52)nb—, and * represents a bond to carbon atoms to which —Ra50 is bonded,
Aa52 represents an alkanediyl group having 1 to 6 carbon atoms,
Xa51 and Xa52 each independently represent —O—, —CO—O— or —O—CO—,
nb represents 0 or 1, and
mb represents an integer of 0 to 4, and when mb is an integer of 2 or more, a plurality of Ra5 may be the same or different from each other.

### Claim 14 (depends on 11)

The resist composition according to claim 11, further comprising a salt generating an acid having an acidity lower than that of an acid generated from the acid generator.

### Claim 15 (depends on 11)

A method for producing a resist pattern, which comprises:
(1) a step of applying the resist composition according to claim 11 on a substrate,
(2) a step of drying the applied resist composition to form a composition layer,
(3) a step of exposing the composition layer,
(4) a step of heating the exposed composition layer, and
(5) a step of developing the heated composition layer.