Photoresist composition, resist pattern-forming method, acid diffusion control agent, and compound

1. A photoresist composition comprising:

a polymer comprising an acid-labile group;

a radiation-sensitive acid generator;

a solvent and

an acid diffusion control agent,

wherein the acid diffusion control agent comprising a compound represented by formula (2):

wherein in the formula (2),

R 1 , R 2 and R 3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, wherein at least two of the monovalent hydrocarbon groups represented by R 1 , R 2 and R 3 optionally join to form a ring structure with the carbon atom to which the at least two of the monovalent hydrocarbon groups bond;

R 4 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms;

R 5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, wherein R 4 and R 5 optionally join to form an alicyclic structure with the nitrogen atom to which R 4 and R 5 bond;

R 6 represents a group having a valency of n that is obtained by combining:

a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 30 carbon atoms or a combination thereof;

—SO 2 O—, —NR—, —NRSO 2 —, —NRSO 2 O— or —CO—CH 2 —CO—; and

optionally, —O—, —CO—, —COO—, —SO 2 O—, —NR—, —NRSO 2 —, —NRSO 2 O—, —NRCO—or a combination thereof,

wherein a part or all of hydrogen atoms included in the linear hydrocarbon group and the alicyclic hydrocarbon group are unsubstituted or substituted with a fluorine atom-free group, and R represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, and in the formula (2), a value obtained by a formula of: {(F 4 +F 5 +F N ) x n+F 6 } is no less than 120, wherein F 4 represents a formula mass of R 4 , F 5 represents a formula mass of R 5 , F N represents an atomic mass of nitrogen, and F 6 represents a formula mass of R 6 ; and

n is an integer of 1 to 4.

2. The photoresist composition according to claim 1 , wherein the compound represented by the formula (2) is represented by formula (3):

wherein in the formula (3),

R 1 , R 2 and R 3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, wherein at least two of the monovalent hydrocarbon groups represented by R 1 , R 2 and R 3 optionally join to form a ring structure with the carbon atom to which the at least two of the monovalent hydrocarbon groups bond;

R 4 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms;

R 5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, wherein R 4 and R 5 optionally join to form an alicyclic structure together with the nitrogen atom to which R 4 and R 5 bond;

R 7 , R 8 and R 9 each independently represent a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 30 carbon atoms or a combination thereof, or a group that is obtained by combining:

a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 30 carbon atoms or a combination thereof; and

—O—, —CO—, —COO—, —SO 2 O—, —NR—, —NRSO 2 —, —NRSO 2 O—, —NRCO— or a combination thereof,

wherein at least two of R 7 , R 8 and R 9 optionally join to form a ring structure with the carbon atom to which the at least two of R 7 , R 8 and R 9 bond; and

X represents —SO 2 O—, —NR—, —NRSO 2 — or —NRSO 2 O,

wherein a sum of formula masses of R 4 , R 5 , X, R 7 , R 8 and R 9 and atomic masses of the nitrogen and the carbon in the formula (3) is no less than 120.

3. The photoresist composition according to claim 1 , further comprising an acid diffusion controller other than the acid diffusion control agent.

4. The photoresist composition according to claim 1 , wherein in the formula (2), the fluorine atom-free group is a cyano group or a nitro group.

5. The photoresist composition according to claim 1 , wherein a value obtained by a formula of: {(F 4 +F 5 +F N )x n+F 6 } is no less than 200.

6. The photoresist composition according to claim 1 , wherein a value obtained by a formula of: {(F 4 +F 5 +F N )x n+F 6 } is no less than 290.

7. The photoresist composition according to claim 1 , wherein a value obtained by a formula of: {(F 4 +F 5 +F N )x n+F 6 } is no greater than 1000.

8. The photoresist composition according to claim 1 , wherein a value obtained by a formula of: {(F 4 +F 5 +F N )x n+F 6 } is no greater than 500.

9. The photoresist composition according to claim 1 , wherein a content of the acid diffusion control agent with respect of the radiation-sensitive acid generator is from 5 mol % to 50 mol %.

10. The photoresist composition according to claim 1 , wherein in the formula (2), the fluorine atom-free group is a cyano group or a nitro group.

11. A resist pattern-forming method, comprising:

applying the photoresist composition according to claim 1 on a substrate to provide a resist film on the substrate;

exposing the resist film; and

developing the resist film exposed.

12. An acid diffusion control agent comprising a compound represented by formula (2):

wherein in the formula (2),

R 1 , R 2 and R 3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, wherein at least two of the monovalent hydrocarbon groups represented by R 1 , R 2 and R 3 optionally join to form a ring structure with the carbon atom to which the at least two of the monovalent hydrocarbon groups bond;

R 4 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms;

R 5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, wherein R 4 and R 5 optionally join to form an alicyclic structure with the nitrogen atom to which R 4 and R 5 bond;

R 6 represents a group having a valency of n that is obtained by combining:

a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 30 carbon atoms or a combination thereof;

—SO 2 O—, —NR—, —NRSO 2 —, —NRSO 2 O— or —CO—CH 2 —CO—;and

optionally —O—, —CO—, —COO—, —SO 2 O—, —NR—, —NRSO 2 —, —NRSO 2 O—, —NRCO—or a combination thereof,

wherein a part or all of hydrogen atoms included in the linear hydrocarbon group and the alicyclic hydrocarbon group are unsubstituted or substituted with a fluorine atom-free group, and R represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, and in the formula (2), a value obtained by a formula of: {(F 4 +F 5 +F N )x n+F 6 } is no less than 120, wherein F 4 represents a formula mass of R 4 , F 5 represents a formula mass of R 5 , F N represents an atomic mass of nitrogen, and F 6 represents a formula mass of R 6 ; and

n is an integer of 1 to 4.

13. The acid diffusion control agent according to claim 12 , wherein the compound represented by the formula (2) is represented by formula (3):

wherein in the formula (3),

R 1 , R 2 and R 3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, wherein at least two of the monovalent hydrocarbon groups represented by R 1 , R 2 and R 3 optionally join to form a ring structure with the carbon atom to which the at least two of the monovalent hydrocarbon groups bond;

R 4 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms;

R 5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, wherein R 4 and R 5 optionally join to form an alicyclic structure with the nitrogen atom to which R 4 and R 5 bond;

R 7 , R 8 and R 9 each independently represent a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 30 carbon atoms or a combination thereof, or a group that is obtained by combining:

a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 30 carbon atoms or a combination thereof; and

—O—, —CO—, —COO—, —SO 2 O—, —NR—, —NRSO 2 —, —NRSO 2 O—, —NRCO— or a combination thereof,

wherein at least two of R 7 , R 8 and R 9 optionally join to form a ring structure with the carbon atom to which the at least two of R 7 , R 8 and R 9 bond; and

X represents —SO 2 O—, —NR—, —NRSO 2 — or —NRSO 2 O—,

wherein a sum of formula masses of R 4 , R 5 , X, R 7 , R 8 and R 9 and atomic masses of the nitrogen and the carbon in the formula (3) is no less than 120.

14. The acid diffusion control agent according to claim 12 , wherein a value obtained by a formula of: {(F 4 +F 5 +F N )x n+F 6 } is no less than 200.

15. The acid diffusion control agent according to claim 12 , wherein a value obtained by a formula of: {(F 4 +F 5 +F N )x n+F 6 } is no less than 290.

16. The acid diffusion control agent according to claim 12 , wherein a value obtained by a formula of: {(F 4 +F 5 +F N )x n+F 6 } is no greater than 1000.

17. The acid diffusion control agent according to claim 12 , wherein a value obtained by a formula of: {(F 4 +F 5 +F N )x n+F 6 } is no greater than 500.

18. A compound represented by formula (3):

wherein in the formula (3),

R 1 , R 2 and R 3 each independently represent a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms, wherein at least two of the monovalent hydrocarbon groups represented by R 1 , R 2 and R 3 optionally join to form a ring structure with the carbon atom to which the at least two of the monovalent hydrocarbon groups bond;

R 4 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms;

R 5 represents a divalent hydrocarbon group having 1 to 10 carbon atoms, wherein R 4 and R 5 optionally join to form an alicyclic structure with the nitrogen atom to which R 4 and R 5 bond;

R 7 , R 8 and R 9 each independently represent a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 30 carbon atoms or a combination thereof, or a group that is obtained by combining:

a hydrogen atom, a linear hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 30 carbon atoms or a combination thereof; and

—O—, —CO—, —COO—, —SO 2 O—, —NR—, —NRSO 2 —, —NRSO 2 O—, —NRCO— or a combination thereof,

wherein at least two of R 7 , R 8 and R 9 optionally join to form a ring structure with the carbon atom to which the at least two of R 7 , R 8 and R 9 bond; and

X represents —SO 2 O—, —NR—, —NRSO 2 — or —NRSO 2 O—,

wherein a sum of formula masses of R 4 , R 5 , X, R 7 , R 8 and R 9 and atomic masses of the nitrogen and the carbon in the formula (3) is no less than 120.