Radiation-sensitive resin composition, resist pattern-forming method, acid diffusion control agent, compound, and method for producing compound

1. A radiation-sensitive resin composition comprising:

a polymer that comprises a structural unit that comprises an acid-labile group; and

a compound represented by formula (1):

wherein in the formula (1),

R 1 represents a monovalent organic group having 1 to 30 carbon atoms;

L represents a single bond, an oxygen atom or a sulfur atom; and

M + represents a monovalent radioactive ray-labile onium cation which is labile to a KrF excimer laser, an ArF excimer laser, an electron beam or an EUV, and

in a case where L represents a single bond, the monovalent radioactive ray-labile onium cation represented by M + is represented by formula (X):

wherein in the formula (X),

R a represents a fluorine atom, a hydroxy group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkoxycarbonyl group having 2 to 11 carbon atoms or an alkylsulfonyl group having 1 to 10 carbon atoms;

j is an integer of 0 to 9, wherein in a case where j is no less than 2, a plurality of R a s are each identical or different;

R b and R c each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or R b and R c taken together represent a ring structure having 4 to 10 ring atoms together with the sulfur atom to which R b and R c bond; and

k is an integer of 0 to 2.

2. The radiation-sensitive resin composition according to claim 1 , wherein the monovalent organic group represented by R 1 in the formula (1) is a monovalent hydrocarbon group or a monovalent fluorinated hydrocarbon group, and L represents the single bond.

3. The radiation-sensitive resin composition according to claim 1 , wherein the monovalent organic group represented by R 1 in the formula (1) is a monovalent hydrocarbon group, a monovalent fluorinated hydrocarbon group, a monovalent aliphatic heterocyclic group or a monovalent fluorinated aliphatic heterocyclic group, and L represents the oxygen atom or the sulfur atom.

4. The radiation-sensitive resin composition according to claim 1 , wherein the monovalent radioactive ray-labile onium cation represented by M + is represented by formula (X).

5. The radiation-sensitive resin composition according to claim 1 , further comprising a radiation-sensitive acid generator.

6. The radiation-sensitive resin composition according to claim 1 , wherein the structural unit is represented by formula (2-1):

wherein in the formula (2-1),

R 2 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group; and

Y 1 is a monovalent acid-labile group represented by formula (Y-1):

wherein in the formula (Y-1),

R e1 represents a monovalent hydrocarbon group having 1 to 20 carbon atoms;

R e2 and R e3 each independently represent a monovalent chain hydrocarbon group having 1 to 10 carbon atoms or a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, or R e2 and R e3 taken together represent an alicyclic structure having 3 to 20 ring carbon atoms together with the carbon atom to which R e2 and R e3 bond.

7. The radiation-sensitive resin composition according to claim 1 , wherein the polymer further comprises a structural unit represented by formula (4):

wherein in the formula (4),

R 6 represents a hydrogen atom or a methyl group;

R 7 represents a monovalent organic group having 1 to 20 carbon atoms;

p is an integer of 0 to 3,

wherein in a case where R 7 is present in a plurality of number, a plurality of R 7 s are each identical or different; and

q is an integer of 1 to 3, wherein a sum of p and q is no greater than 5.

8. A resist pattern-forming method comprising:

applying the radiation-sensitive resin composition according to claim 1 directly or indirectly on a substrate to form a resist film;

exposing the resist film; and

developing the exposed resist film.

9. The radiation-sensitive resin composition according to claim 1 , wherein an amount of the compound is from 0.1 parts to 30 parts by mass with respect to 100 parts by mass of the polymer.

10. The radiation-sensitive resin composition according to claim 1 , wherein an amount of the compound is from 1 part to 5 parts by mass with respect to 100 parts by mass of the polymer.

11. An acid diffusion control agent comprising a compound represented by formula (1):

wherein in the formula (1),

R 1 represents a monovalent organic group having 1 to 30 carbon atoms;

L represents a single bond, an oxygen atom or a sulfur atom; and

M + represents a monovalent radioactive ray-labile onium cation which is labile to a KrF excimer laser, an ArF excimer laser, an electron beam or an EUV, and

in a case where L represents a single bond, the monovalent radioactive ray-labile onium cation represented by M + is represented by formula (X);

wherein in the formula (X),

R a represents a fluorine atom, a hydroxy group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkoxycarbonyl group having 2 to 11 carbon atoms or an alkylsulfonyl group having 1 to 10 carbon atoms;

j is an integer of 0 to 9, wherein in a case where j is no less than 2, a plurality of R a s are each identical or different;

R b and R c each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or R b and R c taken together represent a ring structure having 4 to 10 ring atoms together with the sulfur atom to which R b and R c bond; and

k is an integer of 1 or 2.

12. A compound represented by formula (1):

wherein in the formula (1),

R 1 represents a monovalent organic group having 1 to 30 carbon atoms;

L represents a single bond, an oxygen atom or a sulfur atom; and

M + represents a monovalent radioactive ray-labile onium cation which is labile to a KrF excimer laser, an ArF excimer laser, an electron beam or an EUV, and

in a case where L represents a single bond, the monovalent radioactive ray-labile onium cation represented by M + is represented by formula (X):

wherein in the formula (X),

R a represents a fluorine atom, a hydroxy group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkoxycarbonyl group having 2 to 11 carbon atoms or an alkylsulfonyl group having 1 to 10 carbon atoms;

j is an integer of 0 to 9, wherein in a case where j is no less than 2, a plurality of R a s are each identical or different;

R b and R c each independently represent a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or R b and R c taken together represent a ring structure having 4 to 10 ring atoms together with the sulfur atom to which R b and R c bond; and

k is an integer of 1 or to 2.

13. The compound according to claim 12 , wherein the monovalent organic group represented by R 1 in the formula (1) is a monovalent hydrocarbon group or a monovalent fluorinated hydrocarbon group, and L represents the single bond.

14. The compound according to claim 12 , wherein the monovalent organic group represented by R 1 in the formula (1) is a monovalent hydrocarbon group, a monovalent fluorinated hydrocarbon group, a monovalent aliphatic heterocyclic group or a monovalent fluorinated aliphatic heterocyclic group, and L represents the oxygen atom or the sulfur atom.

15. The compound according to claim 12 , wherein the monovalent radioactive ray-labile onium cation represented by M + is represented by formula (X).