IP Library Granted Patent US 12704782
Granted Patent B2
US 12704782 · App. 18/158,892 · Granted Aug 11, 2026

Actinic ray-sensitive or radiation-sensitive resin composition, actinic ray-sensitive or radiation-sensitive film, pattern forming method, method for manufacturing electronic device, and compound

Inventors: Minoru Uemura (Haibara-gun, JP); Takeshi Kawabata (Haibara-gun, JP); Toshiaki Fukuhara (Haibara-gun, JP); Akinori Shibuya (Haibara-gun, JP); Kei Yamamoto (Haibara-gun, JP)
Assignee: FUJIFILM Corporation
G03F7/038G03F7/039
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Quick Facts
Patent No.
US 12704782
App. No.
18/158,892
Granted
Aug 11, 2026
Kind
B2
Abstract

An actinic ray-sensitive or radiation-sensitive resin composition contains a compound represented by General Formula (I). In General Formula (I), R a and R b each independently represent a hydrogen atom or a substituent, provided that R a and R b satisfy the following requirement (1) or (2): (1) at least one of R a or R b represents a secondary alkyl group, a tertiary alkyl group, a cycloalkyl group, or a perfluoroalkyl group, and R a and R b may be bonded to each other to form a ring, and (2) R a and R b are bonded to each other to form a ring, R c represents a substituent, L 0 represents a single bond or a divalent linking group, L 1 represents a single bond or a divalent linking group, L 2 represents a single bond or a divalent linking group, nM + represents an organic cationic moiety, and n represents an integer of 1 or more.

Claims (167)

1 . A compound represented by General Formula (IA-1),

wherein a carbon anion group represented by Formula (A) is a group represented by any of General Formulae (a-1), (a-2), and (a-5) to (a-9),

in General Formula (IA-1),

R a and R b each independently represent a hydrogen atom or a substituent,

provided that R a and R b satisfy the following requirement (1) or (2);

(1) at least one of R a or R b represents a secondary alkyl group, a tertiary alkyl group, a cycloalkyl group, or a perfluoroalkyl group, and R a and R b may be bonded to each other to form a ring, and

(2) R a and R b are bonded to each other to form a ring,

R c represents a substituent,

L 01 represents a single bond or a divalent linking group,

L 1 represents a single bond or a divalent linking group,

L 2 represents a single bond or a divalent linking group,

nM + represents an organic cationic moiety,

n represents an integer of 1 or more,

R d 's each independently represent a hydrogen atom, a fluorine atom, or an alkyl fluoride group, and

n 1 represents an integer of 1 to 5,

in Formula (A),

* represents a bonding position,

in General Formula (a-1),

R 1 and R 2 each independently represent a hydrogen atom, a secondary alkyl group, a tertiary alkyl group, or a cycloalkyl group,

provided that R 1 and R 2 satisfy the following requirement (1A) or (1B):

(1A) at least one of R 1 or R 2 represents a secondary alkyl group, a tertiary alkyl group, or a cycloalkyl group, and R 1 and R 2 may be bonded to each other to form a ring, and

(1B) R 1 and R 2 are bonded to each other to form a ring,

R e1 's each independently represent a hydrogen atom, a fluorine atom, or an alkyl fluoride group, and

n 11 's each independently represent 0, 1, or 2,

in General Formula (a-2),

R 3 and R 4 each independently represent a hydrogen atom or a substituent,

provided that R 3 and R 4 satisfy the following requirement (2A) or (2B):

(2A) At least one of R 3 or R 4 represents a secondary alkyl group, a tertiary alkyl group, a cycloalkyl group, or a perfluoroalkyl group, and R 3 and R 4 may be bonded to each other to form a ring, and

(2B) R 3 and R 4 are bonded to each other to form a ring,

R e2 's each independently represent a hydrogen atom, a fluorine atom, or an alkyl fluoride group, and

n 12 's each independently represent 0, 1, or 2,

in General Formula (a-5),

R 9 and R 10 each independently represent a hydrogen atom or a substituent, provided that R 9 and R 10 satisfy the following requirement (5A) or (5B):

(5A) At least one of R 9 or R 10 represents a secondary alkyl group, a tertiary alkyl group, a cycloalkyl group, or a perfluoroalkyl group, and R 9 and R 10 may be bonded to each other to form a ring, and

(5B) R 9 and R 10 are bonded to each other to form a ring,

R e5 's each independently represent a hydrogen atom, a fluorine atom, or an alkyl fluoride group, and

n 15 's each independently represent 0, 1, or 2,

in General Formula (a-6),

R 11 and R 12 each independently represent a hydrogen atom or a substituent, provided that R 11 and R 12 satisfy the following requirement (6A) or (6B):

(6A) at least one of R 11 or R 12 represents a secondary alkyl group, a tertiary alkyl group, a cycloalkyl group, or a perfluoroalkyl group, and R 11 and R 12 may be bonded to each other to form a ring, and

(6B) R 11 and R 12 are bonded to each other to form a ring,

R e6 's each independently represent a hydrogen atom, a fluorine atom, or an alkyl fluoride group, and

n 16 's each independently represent 0, 1, or 2,

in General Formula (a-7),

R 13 represents a secondary alkyl group, a tertiary alkyl group, a cycloalkyl group, or a perfluoroalkyl group,

R e7 's each independently represent a hydrogen atom, a fluorine atom, or an alkyl fluoride group, and

n 17 represents 0, 1, or 2,

in General Formula (a-8),

R 14 represents a secondary alkyl group, a tertiary alkyl group, a cycloalkyl group, or a perfluoroalkyl group,

R e8 's each independently represent a hydrogen atom, a fluorine atom, or an alkyl fluoride group, and

n 18 represents 0, 1, or 2,

in General Formula (a-9),

R 15 represents a secondary alkyl group, a tertiary alkyl group, a cycloalkyl group, or a perfluoroalkyl group, R e9 's each independently represent a hydrogen atom, a fluorine atom, or an alkyl fluoride group, and

n 19 represents 0, 1, or 2, and

in General Formulae (a-1), (a-2), and (a-5) to (a-9),

* represents a bonding position.

2 . An actinic ray-sensitive or radiation-sensitive resin composition comprising the compound of claim 1 and an acid decomposable resin.

3 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,

wherein the compound represented by General Formula (IA-1) has at least one fluorine atom.

4 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 2 ,

wherein in General Formula (a-1),

n 11 's each independently represent 0 or 1,

in General Formula (a-2),

n 12 's each independently represent 0 or 1,

in General Formula (a-5),

n 15 's each independently represent 0 or 1,

in General Formula (a-6),

n 16 's each independently represent 0 or 1,

in General Formula (a-7),

n 17 's each independently represent 0 or 1,

in General Formula (a-8),

n 18 's each independently represent 0 or 1, and

in General Formula (a-9),

n 19 's each independently represent 0 or 1.

5 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 ,

wherein in (1A) in General Formula (a-1),

R 1 and R 2 each independently represent a secondary alkyl group, a tertiary alkyl group, or a cycloalkyl group, and R 1 and R 2 may be bonded to each other to form a ring,

in (2A) in General Formula (a-2),

R 3 and R 4 each independently represent a secondary alkyl group, a tertiary alkyl group, a cycloalkyl group, or a perfluoroalkyl group, and R 3 and R 4 may be bonded to each other to form a ring,

in (5A) in General Formula (a-5),

R 9 and R 10 each independently represent a secondary alkyl group, a tertiary alkyl group, a cycloalkyl group, or a perfluoroalkyl group, and R 9 and R 10 may be bonded to each other to form a ring, and

in (6A) in General Formula (a-6),

R 11 and R 12 each independently represent a secondary alkyl group, a tertiary alkyl group, a cycloalkyl group, or a perfluoroalkyl group, and R 11 and R 12 may be bonded to each other to form a ring.

6 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 2 ,

wherein the carbon anion group represented by Formula (A) in the compound represented by General Formula (IA-1) is the group represented by General Formula (a-1) or (a-2).

7 . The actinic ray-sensitive or radiation-sensitive resin composition according to claim 2 ,

wherein R c in the compound represented by General Formula (1-1-1) (IA-1) represents an alkyl group, a cycloalkyl group, an aryl group, or a fluorine atom.

8 . An actinic ray-sensitive or radiation-sensitive film formed of the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 .

9 . A pattern forming method comprising:

forming an actinic ray-sensitive or radiation-sensitive film on a support, using the actinic ray-sensitive or radiation-sensitive resin composition according to claim 2 ;

exposing the actinic ray-sensitive or radiation-sensitive film; and

developing the exposed actinic ray-sensitive or radiation-sensitive film, using a developer.

10 . A method for manufacturing an electronic device, comprising the pattern forming method according to claim 9 .

11 . The compound according to claim 1 ,

wherein R c in the compound represents an alkyl group, a cycloalkyl group, an aryl group, or a fluorine atom.

12 . A compound represented by General Formula (IA),

wherein a carbon anion group represented by Formula (A) is a group represented by any of General Formulae (a-1), (a-2), and (a-5) to (a-9),

in General Formula (IA),

R a and R b each independently represent a hydrogen atom or a substituent,

provided that R a and R b satisfy the following requirement (1) or (2):

(1) at least one of R a or R b represents a secondary alkyl group, a tertiary alkyl group, a cycloalkyl group, or a perfluoroalkyl group, and R a and R b may be bonded to each other to form a ring, and

(2) R a and Rp are bonded to each other to form a ring,

R c represents an anion group, and the anion group is a group represented by any of General Formulae (b-1) to (b-9) below,

L 0 represents a single bond or a divalent linking group,

L 1 represents a single bond or a divalent linking group,

L 2 represents a single bond or a divalent linking group,

nM + represents an organic cationic moiety, and

n represents an integer of 1 or more,

in Formula (A),

* represents a bonding position,

in General Formula (a-1),

R 1 and R 2 each independently represent a hydrogen atom, a secondary alkyl group, a tertiary alkyl group, or a cycloalkyl group,

provided that R 1 and R 2 satisfy the following requirement (1A) or (1B):

(1A) at least one of R 1 or R 2 represents a secondary alkyl group, a tertiary alkyl group, or a cycloalkyl group, and R 1 and R 2 may be bonded to each other to form a ring, and

(1B) R 1 and R 2 are bonded to each other to form a ring,

R e1 's each independently represent a hydrogen atom, a fluorine atom, or an alkyl fluoride group, and

n 11 's each independently represent 0, 1, or 2,

in General Formula (a-2),

R 3 and R 4 each independently represent a hydrogen atom or a substituent,

provided that R 3 and R 4 satisfy the following requirement (2A) or (2B):

(2A) At least one of R 3 or R 4 represents a secondary alkyl group, a tertiary alkyl group, a cycloalkyl group, or a perfluoroalkyl group, and R 3 and R 4 may be bonded to each other to form a ring, and

(2B) R 3 and R 4 are bonded to each other to form a ring,

R e2 's each independently represent a hydrogen atom, a fluorine atom, or an alkyl fluoride group, and

n 12 's each independently represent 0, 1, or 2,

in General Formula (a-5),

R 9 and R 10 each independently represent a hydrogen atom or a substituent,

provided that Ry and R 10 satisfy the following requirement (5A) or (5B):

(5A) At least one of R 9 or R 10 represents a secondary alkyl group, a tertiary alkyl group, a cycloalkyl group, or a perfluoroalkyl group, and R 9 and R 10 may be bonded to each other to form a ring, and

(5B) R 9 and R 10 are bonded to each other to form a ring,

R e5 's each independently represent a hydrogen atom, a fluorine atom, or an alkyl fluoride group, and

n 15 's each independently represent 0, 1, or 2,

in General Formula (a-6),

R 11 and R 12 each independently represent a hydrogen atom or a substituent,

provided that R 11 and R 12 satisfy the following requirement (6A) or (6B):

(6A) at least one of R 11 or R 12 represents a secondary alkyl group, a tertiary alkyl group, a cycloalkyl group, or a perfluoroalkyl group, and R 11 and R 12 may be bonded to each other to form a ring, and

(6B) R 11 and R 12 are bonded to each other to form a ring,

R e6 's each independently represent a hydrogen atom, a fluorine atom, or an alkyl fluoride group, and

n 16 's each independently represent 0, 1, or 2,

in General Formula (a-7),

R 13 represents a secondary alkyl group, a tertiary alkyl group, a cycloalkyl group, or a perfluoroalkyl group,

R e7 's each independently represent a hydrogen atom, a fluorine atom, or an alkyl fluoride group, and

n 17 represents 0, 1, or 2,

in General Formula (a-8),

R 14 represents a secondary alkyl group, a tertiary alkyl group, a cycloalkyl group, or a perfluoroalkyl group,

R e8 's each independently represent a hydrogen atom, a fluorine atom, or an alkyl fluoride group, and

n 18 represents 0, 1, or 2,

in General Formula (a-9),

R 15 represents a secondary alkyl group, a tertiary alkyl group, a cycloalkyl group, or a perfluoroalkyl group, R e9 's each independently represent a hydrogen atom, a fluorine atom, or an alkyl fluoride group, and

n 19 represents 0, 1, or 2, and

in General Formulae (a-1), (a-2) and (a-5) to (a-9),

* represents a bonding position

in General Formula (b-2),

R 21 represents a substituent,

in General Formula (b-3),

R 22 represents a substituent,

in General Formula (b-4),

R 23 represents a substituent,

in General Formula (b-6),

R 24 represents a substituent,

in General Formula (b-7),

R 25 represents a substituent,

in General Formula (b-8),

R 26 represents a substituent,

in General Formula (b-9),

R 27 represents a substituent, and

in General Formulae (b-1) to (b-9),

* represents a bonding position.