Photosensitive composition, compound for use in the photosensitive composition, and pattern forming method using the photosensitive composition

1. A photosensitive composition comprising (A) a compound capable of generating a sulfonic acid, the sulfonic acid being represented by formula (I) upon irradiation with one of an actinic ray and a radiation:

wherein

Rf represents an organic group having a fluorine atom,

R represents a hydroxyl group or an organic group,

Ar represents an aromatic group,

l represents an integer of 2 to 5,

m represents an integer of 0 to 4, and

n represents an integer of 0 to 4,

provided that m+n represents an integer of 1 or more.

2. The photosensitive composition according to claim 1 , wherein the compound (A) comprises at least one of: a sulfonium salt compound of the sulfonic acid represented by formula (I); an iodonium salt compound of the sulfonic acid represented by formula (I); and an ester compound of the sulfonic acid represented by formula (I).

3. The photosensitive composition according to claim 1 ,

wherein the compound (A) is represented by any one of formulae (A1) to (A5):

wherein

in formula (A1),

R 201 , R 202 and R 203 each independently represents an organic group, and

X − represents a sulfonate anion resulting from removal of the hydrogen atom from the sulfonic acid (—SO 3 H) of formula (I);

in formula (A2),

R 204 and R 205 each independently represents an aryl group, an alkyl group or a cycloalkyl group, and

X − represents a sulfonate anion resulting from removal of the hydrogen atom from the sulfonic acid (—SO 3 H) of formula (I);

in formula (A3),

A represents an alkylene group, an alkenylene group or an arylene group, and

X 1 represents a monovalent group resulting from removal of the hydrogen atom from the sulfonic acid (—SO 3 H) of formula (I);

in formula (A4),

R 208 represents an alkyl group or an aryl group,

R 209 represents an alkyl group, a cyano group or an alkoxycarbonyl group, and

X 1 represents a monovalent group resulting from removal of the hydrogen atom from the sulfonic acid (—SO 3 H) of formula (I); and

in formula (A5),

R 210 and R 211 each independently represents a hydrogen atom, an alkyl group, a cyano group, a nitro group or an alkoxycarbonyl group,

R 212 represents a hydrogen atom, an alkyl group, a cyano group or an alkoxycarbonyl group, and

X 1 represents a monovalent group resulting from removal of the hydrogen atom from the sulfonic acid (—SO 3 H) of formula (I).

4. A compound (A) capable of generating a sulfonic acid, the sulfonic acid being represented by formula (I) upon irradiation with one of an actinic ray and a radiation:

wherein

Rf represents an organic group having a fluorine atom,

R represents a hydroxyl group or an organic group,

Ar represents an aromatic group,

l represents an integer of 2 to 5,

m represents an integer of 0 to 4, and

n represents an integer of 0 to 4,

provided that m+n represents an integer of 1 or more.

5. The compound according to claim 4 , wherein the compound (A) comprises at least one of: a sulfonium salt compound of the sulfonic acid represented by formula (I); an iodonium salt compound of the sulfonic acid represented by formula (I); and an ester compound of the sulfonic acid represented by formula (I).

6. A compound represented by formula (I) or a salt thereof:

wherein

Rf represents an organic group having a fluorine atom,

R represents a hydroxyl group or an organic group,

Ar represents an aromatic group,

l represents an integer of 2 to 5,

m represents an integer of 0 to 4, and

n represents an integer of 0 to 4,

provided that m+n represents an integer of 1 or more.

7. A compound represented by any one of formulae (A1) to (A5):

wherein

in formula (A1),

R 201 , R 202 and R 203 each independently represents an organic group, and

X − represents a sulfonate anion resulting from removal of the hydrogen atom from a sulfonic acid (—SO 3 H) of formula (I);

in formula (A2),

R 204 and R 205 each independently represents an aryl group, an alkyl group or a cycloalkyl group, and

X − represents a sulfonate anion resulting from removal of the hydrogen atom from a sulfonic acid (—SO 3 H) of formula (I);

in formula (A3),

A represents an alkylene group, an alkenylene group or an arylene group, and

X 1 represents a monovalent group resulting from removal of the hydrogen atom from a sulfonic acid (—SO 3 H) of formula (I);

in formula (A4),

R 208 represents an alkyl group or an aryl group,

R 209 represents an alkyl group, a cyano group or an alkoxycarbonyl group, and

X 1 represents a monovalent group resulting from removal of the hydrogen atom from a sulfonic acid (—SO 3 H) of the following formula (I); and

in formula (A5),

R 210 and R 211 each independently represents a hydrogen atom, an alkyl group, a cyano group, a nitro group or an alkoxycarbonyl group,

R 212 represents a hydrogen atom, an alkyl group, a cyano group or an alkoxycarbonyl group, and

X 1 represents a monovalent group resulting from removal of the hydrogen atom from a sulfonic acid (—SO 3 H) of formula (I):

wherein

Rf represents an organic group having a fluorine atom,

R represents a hydroxyl group or an organic group,

Ar represents an aromatic group,

l represents an integer of 2 to 5,

m represents an integer of 0 to 4, and

n represents an integer of 0 to 4,

provided that m+n represents an integer of 1 or more.

8. A pattern forming method comprising:

forming a resist film from the photosensitive composition according to claim 1 ; and

exposing and developing the resist film.

9. The photosensitive composition according to claim 1 , which further comprises (A′) a compound capable of generating a sulfonic acid except for formula (I) upon irradiation with one of an actinic ray and a radiation.

10. The photosensitive composition according to claim 9 , wherein the component (A′) is a sulfonium salt of a fluorine-substituted alkanesulfonic acid.

11. A positive photosensitive composition comprising:

(A) a compound capable of generating a sulfonic acid, the sulfonic acid represented by formula (I) upon irradiation with one of an actinic ray and a radiation:

wherein

Rf represents an organic group having a fluorine atom,

R represents a hydroxyl group or an organic group,

Ar represents an aromatic group,

l represents an integer of 2 to 5,

m represents an integer of 0 to 4, and

n represents an integer of 0 to 4,

provided that m+n represents an integer of 1 or more; and

(B) a resin capable of decomposing under the action of an acid to increase a solubility of the resin in an alkali developer.

12. The positive photosensitive composition according to claim 11 , wherein the resin (B) has a fluorine atom.

13. The positive photosensitive composition according to claim 12 , wherein the resin (B) has a hexafluoroisopropanol structure.

14. The positive photosensitive composition according to claim 11 , wherein the resin (B) has a hydroxystyrene structural unit.

15. The positive photosensitive composition according to claim 14 , wherein the resin (B) further has at least one repeating unit selected from 2-alkyl-2-adamantyl (meth)acrylate and dialkyl(1-adamantyl)methyl (meth)acrylate.

16. The positive photosensitive composition according to claim 11 , wherein the resin (B) has a monocyclic or polycyclic alicyclic hydrocarbon structure.

17. The positive photosensitive composition according to claim 16 , wherein the resin (B) has: at least one repeating unit selected from 2-alkyl-2-adamantyl (meth)acrylate and dialkyl(1-adamantyl)methyl (meth)acrylate; at least one repeating unit having a lactone structure; and at least one repeating unit having a hydroxyl group.

18. The positive photosensitive composition according to claim 16 , wherein the resin (B) further has a repeating unit having a carboxyl group.

19. The positive photosensitive composition according to claim 11 , wherein the resin (B) has a silicon atom.

20. The positive photosensitive composition according to claim 11 , wherein the resin (B) further has a repeating unit having a lactone structure.

21. The positive photosensitive composition according to claim 11 , which further comprises (C) a dissolution inhibiting compound capable of decomposing under the action of an acid to increase a solubility of the dissolution inhibiting compound in an alkali developer, the dissolution inhibiting compound having a molecular weight of 3,000 or less.

22. A positive photosensitive composition comprising:

(A) a compound capable of generating a sulfonic acid, the sulfonic acid represented by formula (I) upon irradiation with one of an actinic ray and a radiation:

wherein

Rf represents an organic group having a fluorine atom,

R represents a hydroxyl group or an organic group,

Ar represents an aromatic group,

l represents an integer of 2 to 5,

m represents an integer of 0 to 4, and

n represents an integer of 0 to 4,

provided that m+n represents an integer of 1 or more;

(D) a resin soluble in an alkali developer; and

(C) a dissolution inhibiting compound capable of decomposing under the action of an acid to increase a solubility of the dissolution inhibiting compound in an alkali developer, the dissolution inhibiting compound having a molecular weight of 3,000 or less.

23. A negative photosensitive composition comprising:

(A) a compound capable of generating a sulfonic acid, the sulfonic acid represented by formula (I) upon irradiation with one of an actinic ray and a radiation:

wherein

Rf represents an organic group having a fluorine atom,

R represents a hydroxyl group or an organic group,

Ar represents an aromatic group,

l represents an integer of 2 to 5,

m represents an integer of 0 to 4, and

n represents an integer of 0 to 4,

provided that m+n represents an integer of 1 or more;

(D) a resin soluble in an alkali developer; and

(E) an acid crosslinking agent capable of crosslinking with the alkali developer-soluble resin under the action of an acid.

24. The photosensitive composition according to claim 1 , which further comprises at least one of:

(F) a basic compound; and

(G) a surfactant containing at least one of a fluorine atom and a silicon atom.

25. The photosensitive composition according to claim 11 , which further comprises at least one of:

(F) a basic compound; and

(G) a surfactant containing at least one of a fluorine atom and a silicon atom.

26. The photosensitive composition according to claim 22 , which further comprises at least one of:

(F) a basic compound; and

(G) a surfactant containing at least one of a fluorine atom and a silicon atom.

27. The photosensitive composition according to claim 23 , which further comprises at least one of:

(F) a basic compound; and

(G) a surfactant containing at least one of a fluorine atom and a silicon atom.

28. The photosensitive composition according to claim 24 , wherein the basic compound (F) is at least one of (a) a compound having a structure selected from an imidazole structure, a diazabicyclo structure, an onium hydroxide structure, an onium carboxylate structure, a trialkylamine structure, an aniline structure and a pyridine structure, (b) an alkylamine derivative having at least one of a hydroxyl group and an ether bond, and (c) an aniline derivative having at least one of a hydroxyl group and an ether bond.

29. The photosensitive composition according to claim 25 , wherein the basic compound (F) is at least one of (a) a compound having a structure selected from an imidazole structure, a diazabicyclo structure, an onium hydroxide structure, an onium carboxylate structure, a trialkylamine structure, an aniline structure and a pyridine structure, (b) an alkylamine derivative having at least one of a hydroxyl group and an ether bond, and (c) an aniline derivative having at least one of a hydroxyl group and an ether bond.

30. The photosensitive composition according to claim 26 , wherein the basic compound (F) is at least one of (a) a compound having a structure selected from an imidazole structure, a diazabicyclo structure, an onium hydroxide structure, an onium carboxylate structure, a trialkylamine structure, an aniline structure and a pyridine structure, (b) an alkylamine derivative having at least one of a hydroxyl group and an ether bond, and (c) an aniline derivative having at least one of a hydroxyl group and an ether bond.

31. The photosensitive composition according to claim 27 , wherein the basic compound (F) is at least one of (a) a compound having a structure selected from an imidazole structure, a diazabicyclo structure, an onium hydroxide structure, an onium carboxylate structure, a trialkylamine structure, an aniline structure and a pyridine structure, (b) an alkylamine derivative having at least one of a hydroxyl group and an ether bond, and (c) an aniline derivative having at least one of a hydroxyl group and an ether bond.