Acid diffusion control agent, radiation-sensitive resin composition, resist pattern-forming method, compound, and production method

1. A radiation-sensitive resin composition comprising:

a polymer having an acid-labile group;

an acid generator; and

a first acid diffusion control agent which comprises a compound represented by formula (1), a compound represented by formula (2) or both thereof:

wherein, in the formula (1),

R 1 represents an acid-nonlabile hydrocarbon group comprising a monovalent alicyclic structure and having 3 to 12 carbon atoms, a heteroatom-containing group obtained by inserting —O—, —CO—, —COO—, —SO 2 O—, —NR a SO 2 —, —NR a CO— or a combination thereof between two carbon atoms in the acid-nonlabile hydrocarbon group, or a group obtained by substituting a part or all of hydrogen atoms included in any one of the hydrocarbon group or the heteroatom-containing group with a hydroxy group, a halogen atom or a combination thereof, wherein R a represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms;

R 2 and R 3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, and at least one of R 2 and R 3 represents a monovalent hydrocarbon group having 1 to 10 carbon atoms;

R 4 and R 5 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms; and

R 6 and R 7 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, or R 6 and R 7 taken together represent a ring structure having 3 to 10 ring atoms together with the nitrogen atom to which R 6 and R 7 bond,

in the formula (2),

R 8 represents a monocyclic heterocyclic group having a valency of (n+2) and having 5 to 8 ring atoms together with the ester group to which R 8 bonds and with the carbon atom to which R 10 bonds;

n is an integer of 1 to 6;

R 9 represents a monovalent hydrocarbon group having 1 to 20 carbon atoms, a monovalent heteroatom-containing group comprising —O—, —CO—, —COO—, —SO 2 O—, —NR b SO 2 , —NR b CO— or a combination thereof between two carbon atoms in the monovalent hydrocarbon group, or a group obtained by substituting a part or all of hydrogen atoms included in any one of the monovalent hydrocarbon group or the monovalent heteroatom-containing group with a hydroxy group, a halogen atom or a combination thereof; and optionally, in a case where n is 2 or greater, two or more R 9 s among a plurality of R 9 s taken together represent a ring structure having 3 to 10 ring atoms, a heteroring structure comprising —O—, —CO—, —COO—, —SO 2 O—, —NR b SO 2 , —NR b CO— or a combination thereof between two carbon atoms in the ring structure, or a group obtained by substituting a part or all of hydrogen atoms included in any one of the ring structure or the heteroring structure with a hydroxy group, a halogen atom or a combination thereof, wherein R b represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms;

R 10 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms;

R 11 and R 12 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms; and

R 13 and R 14 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, or R 13 and R 14 taken together represent a ring structure having 3 to 10 ring atoms together with the nitrogen atom to which R 13 and R 14 bond.

2. The radiation-sensitive resin composition according to claim 1 , further comprising a second acid diffusion control agent other than the first acid diffusion control agent.

3. A resist pattern-forming method comprising:

applying the radiation-sensitive resin composition according to claim 1 on a substrate to provide a resist film;

exposing the resist film; and

developing the resist film exposed.

4. The radiation-sensitive resin composition according to claim 1 , wherein the first acid diffusion control agent comprises the compound represented by the formula (1), and in the formula (1), at least one of R 2 and R 3 represents a hydrogen atom.

5. The radiation-sensitive resin composition according to claim 1 , wherein the first acid diffusion control agent comprises the compound represented by the formula (1), and in the formula (1), each of R 4 and R 5 represents a hydrogen atom.

6. The radiation-sensitive resin composition according to claim 1 , wherein the first acid diffusion control agent comprises the compound represented by the formula (1), and in the formula (1), R 6 and R 7 taken together represent the ring structure having 3 to 10 ring atoms together with the nitrogen atom to which R 6 and R 7 bond.

7. The radiation-sensitive resin composition according to claim 1 , wherein the first acid diffusion control agent comprises the compound represented by the formula (2), and in the formula (2), n is 2 or greater, and two or more R 9 s among a plurality of R 9 s taken together represent the ring structure having 3 to 10 ring atoms, the heteroring structure comprising —O—, —CO—, —COO—, —SO 2 O—, —NR b SO 2 , —NR b CO— or a combination thereof between two carbon atoms in the ring structure, or a group obtained by substituting a part or all of hydrogen atoms included in any one of the ring structure or the heteroring structure with a hydroxy group, a halogen atom or a combination thereof, wherein R b represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms.

8. The radiation-sensitive resin composition according to claim 1 , wherein the first acid diffusion control agent comprises the compound represented by the formula (2), and in the formula (2), R 13 and R 14 taken together represent the ring structure having 3 to 10 ring atoms together with the nitrogen atom to which R 13 and R 14 bond.

9. The radiation-sensitive resin composition according to claim 8 , the ring structure or the heteroring structure is a spiro ring structure.

10. A compound represented by formula (1):

wherein, in the formula (1),

R 1 represents an acid-nonlabile hydrocarbon group comprising a monovalent alicyclic structure and having 3 to 12 carbon atoms, a heteroatom-containing group obtained by inserting —O—, —CO—, —COO—, —SO 2 O—, —NR a SO 2 —, —NR a CO— or a combination thereof between two carbon atoms in the acid-nonlabile hydrocarbon group, or a group obtained by substituting a part or all of hydrogen atoms included in any one of the hydrocarbon group or the heteroatom-containing group with a hydroxy group, a halogen atom or a combination thereof, wherein R a represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms;

R 2 and R 3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, and at least one of R 2 and R 3 represents a monovalent hydrocarbon group having 1 to 10 carbon atoms;

R 4 and R 5 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms; and

R 6 and R 7 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, or R 6 and R 7 taken together represent a ring structure having 3 to 10 ring atoms together with the nitrogen atom to which R 6 and R 7 bond.

11. The compound according to claim 10 , wherein in the formula (1), at least one of R 2 and R 3 represents a hydrogen atom.

12. The compound according to claim 10 , wherein in the formula (1), each of R 4 and R 5 represents a hydrogen atom.

13. The compound according to claim 10 , wherein in the formula (1), R 6 and R 7 taken together represent the ring structure having 3 to 10 ring atoms together with the nitrogen atom to which R 6 and R 7 bond.

14. A production method comprising reacting a compound represented by formula (i-a) and an amine compound represented by formula (i-b) to produce a compound represented by formula (1):

wherein, in the formulae (i-a), (i-b) and (1),

R 1 represents an acid-nonlabile hydrocarbon group comprising a monovalent alicyclic structure and having 3 to 12 carbon atoms, a heteroatom-containing group obtained by inserting —O—, —CO—, —COO—, —SO 2 O—, —NR a SO 2 —, —NR a CO— or a combination thereof between two carbon atoms in the acid-nonlabile hydrocarbon group, or a group obtained by substituting a part or all of hydrogen atoms included in any one of the hydrocarbon group or the heteroatom-containing group with a hydroxy group, a halogen atom or a combination thereof, wherein R a represents a hydrogen atom or a hydrocarbon group having 1 to 10 carbon atoms;

R 2 and R 3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, and at least one of R 2 and R 3 represents a monovalent hydrocarbon group having 1 to 10 carbon atoms;

R 4 and R 5 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms; and

R 6 and R 7 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, or R 6 and R 7 taken together represent a ring structure having 3 to 10 ring atoms together with the nitrogen atom to which R 6 and R 7 bond.