Salt, acid generator, resist composition and method for producing resist pattern

Patent metadata

Field	Value
Publication number	US-11820736-B2
Application number	US-202217718748-A
Country	US
Kind code	B2
Filing date	Apr 12, 2022
Priority date	Apr 15, 2021
Publication date	Nov 21, 2023
Grant date	Nov 21, 2023

Abstract

Disclosed are a salt represented by formula (I), an acid generator, and a resist composition including the same:

wherein R 1 , R 2 and R 3 each represent a hydroxy group, *—O—R 10 , *—O—CO—O—R 10 , etc.; L 10 represents an alkanediyl group; R 10 represents an acid-labile group; R 4 , R 5 , R 6 , R 7 , R 8 and R 9 each represent a halogen atom, a haloalkyl group or a hydrocarbon group; A 1 , A 2 and A 3 each represent a hydrocarbon group which may have a substituent, and —CH 2 — included in the hydrocarbon group may be replaced by —O—, —CO—, —S— or —SO 2 —; m1 represents an integer of 1 to 5, m2, m3, m8 and m9 represent an integer of 0 to 5, m4 to m7 represent an integer of 0 to 4, 1≤m1+m7≤5, 0≤m2+m8≤5, 0≤m3+m9≤5; and AI − represents an organic anion.

First claim

What is claimed is:

1. A salt represented by formula (I):

wherein, in formula (I),
R 1 , R 2 and R 3 each independently represent a hydroxy group, *—O—R 10 , * —O—CO—O—R 10 or *—O-L 10 -CO—O—R 10 , and * represents a bonding site to the benzene ring,
L 10 represents an alkanediyl group having 1 to 6 carbon atoms,
R 10 represents an acid-labile group,
R 4 , R 5 , R 6 , R 7 , R 8 and R 9 each independently represent a halogen atom, a haloalkyl 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 —CH 2 — included in the haloalkyl group and the hydrocarbon group may be replaced by —O—, —S—, —CO— or —SO 2 —,
A 1 , A 2 and A 3 each independently represent a hydrocarbon group having 2 to 20 carbon atoms, the hydrocarbon group may have a substituent, and —CH 2 — included in the hydrocarbon group may be replaced by —O—, —CO—, —S— or —SO 2 —,
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,
m4 represents an integer of 0 to 4, and when m4 is 2 or more, a plurality of R 4 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 R 5 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 R 6 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 R 7 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 R 8 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 R 9 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 a sulfonic acid anion, a sulfonylimide anion, a sulfonylmethide anion or a carboxylic acid anion, provided that the sulfonic acid anion does not comprise a structure represented by —C(H)(F)—C(F)(F)—SO 3 − .

2. The salt according to claim 1 , wherein A 1 is *—X 01 -L 01 - or *-L 01 -X 01 —, A 2 is *—X 02 -L 02 - or *-L 02 -X 02 — and A 3 is *—X 03 -L 03 - or *-L 03 -X 03 —, wherein X 01 , X 02 and X 03 each independently represent —O—, —CO—, —S— or —SO 2 —, L 01 , L 02 and L 03 each independently represent a hydrocarbon group having 1 to 19 carbon atoms, the hydrocarbon group may have a substituent, —CH 2 — included in the hydrocarbon group may be replaced by —O—, —CO—, —S— or —SO 2 —, and * represents a bonding site to the benzene ring to which R 1 , R 2 or R 3 is bonded.

3. The salt according to claim 2 , wherein X 01 , X 02 and X 03 are each independently —O— or —S—.

4. The salt according to claim 2 , wherein L 01 , L 02 and L 03 are each independently an alkanediyl group having 1 to 6 carbon atoms and —CH 2 — included in the alkanediyl group may be replaced by —O— or —CO—.

5. The salt according to claim 1 , wherein R 1 , R 2 and R 3 are each independently a hydroxy group, *—O—R 10 or *—O-L 10 -CO—O—R 10 and * represents a bonding site to the benzene ring.

6. The salt according to claim 1 , wherein the acid-labile group as for R 10 is a group represented by formula (1a) or a group represented by formula (2a):

wherein, in formula (1a), Raa1, R aa1 , R aa2 and R aa3 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 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group obtained by combining these groups, or R aa1 and R aa2 may be bonded to each other to form an alicyclic hydrocarbon group having 3 to 20 carbon atoms together with carbon atoms to which R aa1 and R aa2 are bonded, and
* represents a bonding site:

wherein, in formula (2a), R aa1′ and R aa2′ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, R aa3′ represents a hydrocarbon group having 1 to 20 carbon atoms, or R aa2′ and R aa3′ may be bonded to each other to form a heterocyclic group having 3 to 20 carbon atoms together with —C—X a — to which R aa2′ and R aa3′ are bonded, and —CH 2 — included in the hydrocarbon group and the heterocyclic group may be replaced by —O— or —S—,
X a represents an oxygen atom or a sulfur atom, and
* represents a bonding site.

7. The salt according to claim 1 , wherein when m4, m5 or m6 is an integer of 1 or more, R 4 , R 5 and R 6 are each independently a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms and —CH 2 — included in the alkyl group may be replaced by —O— or —CO—.

8. The salt according to claim 1 , wherein when m7, m8 or m9 is an integer of 1 or more, R 7 , R 8 and R 9 are each independently a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms and —CH 2 — included in the alkyl group may be replaced by —O— or —CO—.

9. 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),
Q 1 and Q 2 each independently represent a hydrogen atom, a fluorine atom, an alkyl group having 1 to 6 carbon atoms or a perfluoroalkyl group having 1 to 6 carbon atoms,
L 1 represents a saturated hydrocarbon group having 1 to 24 carbon atoms, —CH 2 — 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, provided that when Q 1 and Q 2 are fluorine atoms, the group directly attached to —C(Q 1 )(Q 2 )- is not —C(H)(F)—, and
Y 1 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 —CH 2 — included in the alicyclic hydrocarbon group may be replaced by —O—, —S—, —SO 2 — or —CO—.

10. An acid generator comprising the salt according to claim 1 .

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

12. The resist composition according to claim 11 , wherein the resin having an acid-labile group includes at least one selected from the group consisting of a structural unit represented by formula (a1-0), a structural unit represented by formula (a1-1) and a structural unit represented by formula (a1-2):

wherein, in formula (a1-0), formula (a1-1) and formula (a1-2),
L a01 , L a1 and L a2 each independently represent —O— or *—O—(CH 2 ) k1 —CO—O—, k1 represents an integer of 1 to 7, and * repre

Assignees

• Sumitomo Chemical Co

Inventors

• Komuro Katsuhiro
• Ichikawa Koji

Classifications

• C07C381/12 Primary

  Sulfonium compounds · CPC title

• G03F7/0045 Primary

  with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors · CPC title

• G03F7/162

  Coating on a rotating support, e.g. using a whirler or a spinner · CPC title

• C07C323/20 Primary

  with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring · CPC title

• G03F7/0392

  the macromolecular compound being present in a chemically amplified positive photoresist composition · CPC title