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

Patent metadata

Field	Value
Publication number	US-2022372012-A1
Application number	US-202217717305-A
Country	US
Kind code	A1
Filing date	Apr 11, 2022
Priority date	Apr 15, 2021
Publication date	Nov 24, 2022
Grant date	—

Abstract

Provided are a salt capable of producing a resist pattern with satisfactory CD Uniformity (CDU), an acid generator, and a resist composition. Disclosed are a salt represented by formula (I), an acid generator, and a resist composition:wherein, in formula (I), R4, R5, R6, R7, R8 and R9 each represent a halogen atom, a haloalkyl group, etc.; A1, A2 and A3 each represent a hydrocarbon group, etc.; m1 and m4, m5, m6 and m7 represent an integer of 0 to 5, m2, m3, m8 and m9 represent an integer of 0 to 4, 0≤m1+m7≤5, 0≤m2+m8≤4, 0≤m3+m9≤4, and at least one of m1, m2 and m3 represents an integer of 1 or more; X4 represents a single bond, —CH2—, —O—, —S—, —CO—, —SO— or —SO2—; and AI− represents an organic anion.

First claim

1 . A salt represented by formula (I):

wherein, in formula (I),
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 one of —CH 2 — included in the hydrocarbon group may be replaced by —O—, —CO—, —S— or —SO 2 —,
m1 represents an integer of 0 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 4, 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 4, 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 5, 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 5, 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 5, 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 5, 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 4, 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 4, and when m9 is 2 or more, a plurality of R 9 may be the same or different from each other,
in which 0≤m1+m7≤5, 0≤m2+m8≤s 4, 0≤m3+m9≤s4, and at least one of m1, m2 and m3 represents an integer of 1 or more,
X 4 represents a single bond, —CH 2 —, —O—, —S—, —CO—, —SO— or —SO 2 —, and
AI − represents an organic anion.

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 — (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, and * represents a bonding site to the benzene ring to which R 4 , R 5 or R 6 may be 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.

5 . 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 (—CH 2 — included in the alkyl group may be replaced by —O— or —CO—).

6 . 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 (—CH 2 — included in the alkyl group may be replaced by —O— or —CO—).

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

8 . 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, 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—.

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

10 . A resist composition comprising the acid generator according to claim 9 and a resin having an acid-labile group.

11 . The resist composition according to claim 10 , 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 * represents a bonding site to —CO—,
R a01 , R a4 and R a5 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,
R a02 , R a03 and R a04 each independently represent an alkyl group having 1 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,
R a6 and R a7 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 formed 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.

12 . The resist composition according to claim 10 , wherein the resin having an acid-labile group includes a structural unit represented by formula (a2-A):

wherein, in formula (a2-A),
R a50 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom,
R a51 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,
A a50 represents a single bond or *—X a51 -(A a52 -X a52 ) nb —, and * represents a bonding site to carbon atoms to which —R a50 is bonded,
A a52 represents an alkanediyl group having 1 to 6 carbon atoms,
X a51 and X a52 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 R a51 may be the same or different from each other.

Assignees

• Sumitomo Chemical Co

Inventors

• Komuro Katsuhiro
• Oguma Jun
• Ichikawa Koji

Classifications

• C07C309/12

  containing esterified hydroxy groups bound to the carbon skeleton · CPC title

• C07C309/17

  containing carboxyl groups bound to the carbon skeleton · CPC title

• G03F7/0392

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

• G03F7/038

  Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021) · CPC title

• G03F7/20

  Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00) · CPC title