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

1. An actinic ray-sensitive or radiation-sensitive resin composition comprising:

a resin whose solubility in a developer is changed by the action of an acid; and

a photoacid generator represented by General Formula (b1),

wherein the photoacid generator represented by General Formula (b1) is a compound that generates an acid having a pka of 1.0 or less upon irradiation with actinic rays or radiation,

in General Formula (b1),

R 1 represents a substituent,

R 2 represents a group forming a having at least one heteroatom other than S + , which may have a substituent, together with S + , and

an aromatic ring group is not disposed at at least one of a position bonded to S + in R 1 and two positions bonded to S + in R 2 ,

provided that the substituent represented by R 1 has an anionic group which is a group having a sulfonate anion group or the group represented by R 2 has an anionic group which is a group having a sulfonate anion group.

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

wherein the anionic group is a group represented by General Formula (b1-1),

in General Formula (b1-1),

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

V 1 represents a single bond or a hydrocarbon group which may have a fluorine atom, and

* represents a bonding position.

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

wherein the photoacid generator represented by General Formula (b1) is a compound represented by General Formula (ZI-3) or a compound represented by General Formula (ZI-4),

in General Formula (ZI-3),

R 1c to R 5c each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, a cycloalkylcarbonyloxy group, a halogen atom, a hydroxyl group, a nitro group, an alkylthio group, an arylthio group, or an anionic group,

R 6c and R 7c each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, an aryl group, or an anionic group, and

R 2 represents a group forming a heterocycle having at least one heteroatom other than S + , which may have a substituent, together with S + ,

provided that any one of R 1c , . . . , or R 7c , is an anionic group which is the group represented by General Formula (b1-1), or R 2 is a group having an anionic group which is the group represented by General Formula (b1-1),

in General Formula (ZI-4),

l represents an integer of 0 to 2,

r represents an integer of 0 to 8,

R 13 represents a group having a hydrogen atom, a fluorine atom, a hydroxyl group, an alkyl group, an alkoxy group, an alkoxycarbonyl group, a cycloalkyl group, or an anionic group,

R 14 represents a hydroxyl group, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylsulfonyl group, a cycloalkylsulfonyl group, a group having a cycloalkyl group, or an anionic group,

R 2 represents a group forming a heterocycle having at least one heteroatom other than S + , which may have a substituent, together with S + , and

an aromatic ring group is not disposed at at least one of the two positions bonded to S + in R 2 ,

provided that any one of R 13 and any one of R 14 's which may be present in a plural number are each an anionic group which is the group represented by General Formula (b1-1), or R 2 is a group having an anionic group which is the group represented by General Formula (b1-1).

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

wherein the photoacid generator represented by General Formula (b1) is a compound represented by General Formula (ZI-3) or a compound represented by General Formula (ZI-4),

in General Formula (ZI-3),

R 1c to R 5c each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an alkylcarbonyloxy group, a cycloalkylcarbonyloxy group, a halogen atom, a hydroxyl group, a nitro group, an alkylthio group, an arylthio group, or an anionic group,

R 6c and R 7c each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, a halogen atom, a cyano group, an aryl group, or an anionic group, and

R 2 represents a group forming a heterocycle having at least one heteroatom other than S + , which may have a substituent, together with S + ,

provided that any one of R 1c , . . . , or R 7c is an anionic group which is a group having a sulfonate anion group, or R 2 is a group having an anionic group which is a group having a sulfonate anion group,

in General Formula (ZI-4),

l represents an integer of 0 to 2,

r represents an integer of 0 to 8,

R 13 represents a group having a hydrogen atom, a fluorine atom, a hydroxyl group, an alkyl group, an alkoxy group, an alkoxycarbonyl group, a cycloalkyl group, or an anionic group,

R 14 represents a hydroxyl group, an alkyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylsulfonyl group, a cycloalkylsulfonyl group, a group having a cycloalkyl group, or an anionic group,

R 2 represents a group forming a heterocycle having at least one heteroatom other than S + , which may have a substituent, together with S + , and

an aromatic ring group is not disposed at at least one of the two positions bonded to S + in R 2 ,

provided that any one of R 13 and any one of R 14 's which may be present in a plural number are each an anionic group which is a group having a sulfonate anion group, or R 2 is a group having an anionic group which is a group having a sulfonate anion group.

5. The actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 , further comprising an acid diffusion control agent.

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

wherein the acid diffusion control agent is a basic compound whose basicity is reduced or lost upon irradiation with actinic rays or radiation, with the compound being different from the photoacid generator represented by General Formula (b1).

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

wherein the basic compound whose basicity is reduced or lost upon irradiation with actinic rays or radiation is a compound having an anion represented by General Formula (c-1),

Q-A-X—B—R  ( c -1)

in General Formula (c-1),

Q represents —SO 3 − , —CO 2 − , or —W 1 —N − —W 2 R f ,

W 1 and W 2 each independently represent —SO 2 — or —CO—,

R f represents an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, or an aryl group which may have a substituent,

A represents a single bond or a divalent linking group,

X represents a single bond, —SO 2 —, or —CO—,

B represents a single bond, an oxygen atom, or —N(R x ) R y —,

R x represents a hydrogen atom or an organic group,

R y represents a single bond or a divalent organic group,

R represents a monovalent organic group having a proton-accepting functional group, and

R x may be bonded to R y to form a ring, and may be bonded to R to form a ring.

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

wherein a pka of an acid generated by the basic compound whose basicity is reduced or lost upon irradiation with actinic rays or radiation is more than 1.0.

9. A resist film formed using the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 .

10. A pattern forming method comprising:

a step of forming a resist film using the actinic ray-sensitive or radiation-sensitive resin composition according to claim 1 on a support;

a step of exposing the resist film; and

a step of developing the exposed resist film using a developer.

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

12. A resist film formed using the actinic ray-sensitive or radiation-sensitive resin composition according to claim 2 .

13. A pattern forming method comprising:

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

a step of exposing the resist film; and

a step of developing the exposed resist film using a developer.

14. A method for manufacturing an electronic device, comprising the pattern forming method according to claim 13 .

15. A resist film formed using the actinic ray-sensitive or radiation-sensitive resin composition according to claim 4 .