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
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.
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.