Resist composition, compound, polymeric compound and method of forming resist pattern

1. A resist comprising:

a base component (A) which exhibits changed solubility in a developing solution under action of acid,

a solvent, and

an acid generator component (B0) comprising a compound (B0-1) represented by general formula (b0) shown below:

wherein Rb 1 represents a perfluoroalkyl group of 1 to 4 carbon atoms, a nitro group, a hydroxy group, a cyano group, an acyl group of 1 to 4 carbon atoms or a halogen atom; Rb 2 and Rh 3 each independently represents an unsubstituted phenyl group; and X1 − represents a monovalent counteranion capable of generating a strong acid.

2. The resist composition according to claim 1 , which further comprises an acid diffusion control agent (D).

3. The resist composition according to claim 2 , wherein the acid diffusion control agent (D) comprises a compound (D0) represented by general formula (d0) shown below:

wherein Rb 1 represents an electron withdrawing group; Rb 2 and Rb 3 each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent or an alkenyl group which may have a substituent, provided that Rb 2 and Rb 3 may be mutually bonded to form a ring with the sulfur atom; and X2 − represents a monovalent counteranion capable of generating a weak acid.

4. A resist composition comprising:

a base component (A) which exhibits changed solubility in a developing solution under action of acid,

a solvent, and

an acid diffusion control agent (D) comprising a compound (D0) represented by general formula (d0) shown below:

wherein Rb 1 represents a perfluoroalkyl group of 1 to 4 carbon atoms, a nitro group, a hydroxy group, a cyano group, an acyl group of 1 to 4 carbon atoms or a halogen atom; Rb 2 and Rb 3 each independently represents an unsubstituted phenyl group; and X2 − represents a monovalent counteranion capable of generating a weak acid.

5. The resist composition according to claim 4 , which further comprises an acid generator component (B) which generates acid upon exposure.

6. The resist composition according to claim 5 , wherein the acid generator component (B) comprises a compound (B0-1) represented by general formula (b0) shown below:

wherein Rb 1 represents an electron withdrawing group; Rb 2 and Rb 3 each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent or an alkenyl group which may have a substituent, provided that Rb 2 and Rb 3 may be mutually bonded to form a ring with the sulfur atom; and X1 − represents a monovalent counteranion capable of generating a strong acid.

7. A compound (B11) represented by general formula (B11) shown below:

wherein Rb 1 represents a perfluoroalkyl group of 1 to 4 carbon atoms, a nitro group, a hydroxy group, a cyano group, an acyl group of 1 to 4 carbon atoms or a halogen atom; Rb 2 and Rb 3 each independently represents an unsubstituted phenyl group; and X11 − is a counteranion represented by any one of formulae (b11-1) to (b11-3); Rb 101 , Rb 104 and Rb 105 each independently represents a cyclic group which may have a substituent or a chain-like alkenyl group which may have a substituent; Rb 106 to Rb 108 each independently represents a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent or a chain-like alkenyl group which may have a substituent; provided that Rb 104 and Rb 105 may be mutually bonded to form a ring; Rb 106 and Rb 107 may be mutually bonded to form a ring; Rb 102 represents a fluorine atom or a fluorinated alkyl group of 1 to 5 carbon atoms; Yb 101 represents a single bond or a divalent linking group containing an oxygen atom; Vb 101 to Vb 103 each independently represents a single bond, an alkylene group or a fluorinated alkylene group; Lb 101 and Lb 102 each independently represents a single bond or an oxygen atom; Lb 103 to Lb 105 each independently represents a single bond, —CO— or —SO 2 —.

8. A polymeric compound (A0-B11) comprising a structural unit derived from a compound (B11-01) represented by general formula (B11-01) shown below:

wherein Rb 1 represents a perfluoroalkyl group of 1 to 4 carbon atoms, nitro group, a hydroxy group, a cyano group, an acyl group of 1 to 4 carbon atoms or a halogen atom; Rb 2 and Rb 3 each independently represents an unsubstituted phenyl group; and X11-1 − is a counteranion represented by any one of formulae (b11-01-1) to (b11-01-3); Rb 201 represents a chain-like alkenyl group which may have a substituent; Rb 204 and Rb 205 each independently represents a cyclic group which may have a substituent or a chain-like alkenyl group which may have a substituent, provided that at least one of Rb 204 and Rb 205 represents a chain-like alkenyl group which may have a substituent; Rb 206 to Rb 208 each independently represents a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent or a chain-like alkenyl group which may have a substituent (provided that at least one of Rb 206 to Rb 208 represents a chain-like alkenyl group which may have a substituent); Rb 102 represents a fluorine atom or a fluorinated alkyl group of 1 to 5 carbon atoms; Yb 101 represents a single bond or a divalent linking group containing an oxygen atom; Vb 101 to Vb 103 each independently represents a single bond, an alkylene group or a fluorinated alkylene group; Lb 101 and Lb 102 each independently represents a single bond or an oxygen atom; Lb 103 to Lb 105 each independently represents a single bond, —CO— or —SO 2 —.

9. A resist composition comprising: the polymeric compound (A0-B11) of claim 8 ,

a solvent, and

optionally a base component (A) which exhibits changed solubility in a developing solution under action of acid.

10. The resist composition according to claim 9 , which further comprises an acid diffusion control agent (D).

11. The resist composition according to claim 10 , wherein the acid diffusion control agent (D) comprises a compound (D0) represented by general formula (d0):

wherein Rb 1 represents an electron withdrawing group; Rb 2 and Rb 3 each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent or an alkenyl group which may have a substituent, provided that Rb 2 and Rb 3 may be mutually bonded to form a ring with the sulfur atom; and X2 − represents a monovalent counteranion capable of generating a weak acid.

12. A compound (D11) represented by general formula (D11) shown below:

wherein Rb 1 represents a perfluoroalkyl group of 1 to 4 carbon atoms, nitro group, a hydroxy group, a cyano group, an acyl group of 1 to 4 carbon atoms or a halogen atom; Rb 2 and Rb 3 each independently represents an unsubstituted phenyl group; and X21 − is a counteranion represented by any one of formulae (d11-1) to (d11-3); Rd 10 represents a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent or a chain-like alkenyl group which may have a substituent; Rd 20 represents a chain-like alkenyl group which may have a substituent, a chain-like alkyl group which may have a substituent or an aliphatic cyclic group which may have a substituent, provided that 10-camphorsulfonate is excluded from formula (d11-2); Rd 30 and Rd 40 each independently represents a cyclic group which may have a substituent, a chain-like alkyl group which may have a substituent or a chain-like alkenyl group which may have a substituent; provided that, the carbon atom adjacent to the S atom within the Rd 20 group in formula (d11-2) has no fluorine atom bonded thereto; Yd 10 represents a single bond or a divalent linking group.

13. A polymeric compound (A0-D11) comprising a structural unit derived from a compound (D11-01) represented by general formula (D11-01) shown below:

wherein Rb 1 represents a perfluoroalkyl group of 1 to 4 carbon atoms, a nitro group, a hydroxy group, a cyano group, an acyl group of 1 to 4 carbon atoms or a halogen atom; Rb 2 and Rb 3 each independently represents an unsubstituted phenyl group; and X21-1 − is a counteranion represented by any one of formulae (d11-01-1) to (d11-01-3); Rd 100 represents a chain-like alkenyl group which may have a substituent; Rd 200 represents a chain-like alkenyl group which may have a substituent; at least one of Rd 300 and Rd 400 represents a chain-like alkenyl group which may have a substituent; provided that, the carbon atom adjacent to the S atom within the Rd 200 group in formula (d11-01-2) has no fluorine atom bonded thereto; Yd 10 represents a single bond or a divalent linking group.

14. A resist composition comprising: the polymeric compound (A0-D11) of claim 13 ,

a solvent, and

optionally a base component (A) which exhibits changed solubility in a developing solution under action of acid.

15. The resist composition according to claim 14 , further comprising an acid generator component (B) which generates acid upon exposure.

16. The resist composition according to claim 15 , wherein the acid generator component (B) comprises a compound (B1) represented by general formula (b1) shown below:

wherein Rb 1 represents an electron withdrawing group; Rb 2 and Rb 3 each independently represents an aryl group, an alkyl group or an alkenyl group, provided that Rb 2 and Rb 3 may be mutually bonded to form a ring with the sulfur atom; and X1 − represents a monovalent counteranion capable of generating a strong acid.

17. A method of forming a resist pattern, comprising:

forming a resist film on a substrate using a resist composition of claim 9 ; exposing the resist film; and

developing the resist film to form a resist pattern.

18. A method of forming a resist pattern, comprising:

forming a resist film on a substrate using a resist composition of claim 14 ; exposing the resist film; and

developing the resist film to form a resist pattern.