Radiation-sensitive resin composition, resist pattern-forming method, compound, and method of controlling acid diffusion

1. A radiation-sensitive resin composition comprising:

a polymer comprising a structural unit comprising an acid-labile group; and

a compound represented by formula (1):

wherein, in the formula (1),

Ar 1 represents a group obtained by removing (m+n+2) hydrogen atoms from an aromatic ring of an arene having 6 to 30 carbon atoms;

—OH and —COO— are bonded at ortho positions to each other on a same benzene ring on Ar 1 ;

m is an integer of 1 to 16, wherein

in a case in which m is 1, R G represents a group represented by formula (V-1), a group represented by formula (V-2), a group comprising a lactone structure, a group comprising a cyclic carbonate structure, a group comprising a sultone structure, a group comprising a ketonic carbonyl group, a group comprising a thiocarbonate group, or a group comprising a group represented by formula (V-3), and

in a case in which m is no less than 2, a plurality of R G s are identical or different from each other, and each R G represents a group represented by the formula (V-1), a group represented by the formula (V-2), a group comprising a lactone structure, a group comprising a cyclic carbonate structure, a group comprising a sultone structure, a group comprising a ketonic carbonyl group, a group comprising a thiocarbonate group, or a group comprising a group represented by the formula (V-3), or the plurality of R G s taken together represent a part of a ring structure having 5 to 20 ring atoms constituted together with the atomic chain to which the plurality of R G s bond;

n is an integer of 0 to 15, wherein

in a case in which n is 1, R H represents a halogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and

in a case in which n is no less than 2, a plurality of R H s are identical or different from each other, and each R H represents a halogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, or the plurality of R H s taken together represent a part of an alicyclic structure having 4 to 20 ring atoms constituted together with the carbon chain to which the plurality of R H s bond, and wherein

a sum of m and n is no greater than 16; and

M + is a monovalent radiation-sensitive cation,

in the formula (V-1),

R 1 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms;

R 2 represents a monovalent organic group having 1 to 20 carbon atoms; and

* denotes a binding site to an oxygen atom adjacent to Ar 1 in the formula (1),

in the formula (V-2),

R 3 and R 4 each independently represent a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms;

R 5 represents —O— or —S—; and

R 6 represents a monovalent organic group having 1 to 20 carbon atoms, or

R 4 , R 5 , and R 6 taken together represent a part of a ring structure having 4 to 20 ring atoms constituted together with the atomic chain to which R 4 , R 5 , and R 6 bond; and

* denotes a binding site to an oxygen atom adjacent to Ar 1 in the formula (1), and

in the formula (V-3),

R 7 represents a fluorine atom or a monovalent fluorinated hydrocarbon group having 1 to 20 carbon atoms;

R 8 represents a hydrogen atom, a fluorine atom, or a monovalent organic group having 1 to 20 carbon atoms;

R 9 represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms; and

** denotes a binding site to an oxygen atom adjacent to Ar 1 in the formula (1) or to a part other than the group represented by the formula (V-3) in R G .

2. The radiation-sensitive resin composition according to claim 1 , further comprising an acid generator which is capable of generating an acid by irradiation with a radioactive ray.

3. The radiation-sensitive resin composition according to claim 1 , wherein R 2 in the formula (V-1), R 6 in the formula (V-2), and R 9 in the formula (V-3) each independently represent a monovalent hydrocarbon group having 1 to 20 carbon atoms in which a part or all of hydrogen atoms are optionally substituted with a hetero atom-containing group; or a monovalent group that includes a divalent hetero atom-containing group between two adjacent carbon atoms of or at an end of the monovalent hydrocarbon group in which a part or all of hydrogen atoms are optionally substituted with a hetero atom-containing group.

4. The radiation-sensitive resin composition according to claim 1 , wherein R G in the formula (1) represents a group comprising a lactone structure, a group comprising a cyclic carbonate structure, or a group comprising a sultone structure.

5. The radiation-sensitive resin composition according to claim 1 , wherein R G in the formula (1) represents a group represented by the formula (V-1).

6. The radiation-sensitive resin composition according to claim 5 , wherein R 2 in the formula (V-1) represents a monovalent organic group having 1 to 20 carbon atoms and having a ring structure with 3 to 12 ring atoms.

7. The radiation-sensitive resin composition according to claim 1 , wherein m in the formula (1) is 2, and two R G s each independently represent a group represented by the formula (V-1).

8. A resist pattern-forming method comprising:

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

exposing the resist film; and

developing the resist film exposed, wherein

the radiation-sensitive resin composition comprises:

a polymer comprising a structural unit comprising an acid-labile group; and

a compound represented by formula (1):

wherein, in the formula (1),

Ar 1 represents a group obtained by removing (m+n+2) hydrogen atoms from an aromatic ring of an arene having 6 to 30 carbon atoms;

—OH and —COO— are bonded at ortho positions to each other on a same benzene ring on Ar 1 ;

m is an integer of 1 to 16, wherein

in a case in which m is 1, R G represents a group represented by formula (V-1), a group represented by formula (V-2), a group comprising a lactone structure, a group comprising a cyclic carbonate structure, a group comprising a sultone structure, a group comprising a ketonic carbonyl group, a group comprising a thiocarbonate group, or a group comprising a group represented by formula (V-3), and

in a case in which m is no less than 2, a plurality of R G s are identical or different from each other, and each R G represents a group represented by the formula (V-1), a group represented by the formula (V-2), a group comprising a lactone structure, a group comprising a cyclic carbonate structure, a group comprising a sultone structure, a group comprising a ketonic carbonyl group, a group comprising a thiocarbonate group, or a group comprising a group represented by the formula (V-3), or the plurality of R G s taken together represent a part of a ring structure having 5 to 20 ring atoms constituted together with the atomic chain to which the plurality of R G s bond;

n is an integer of 0 to 15, wherein

in a case in which n is 1, R H represents a halogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and

in a case in which n is no less than 2, a plurality of R H s are identical or different from each other, and each R H represents a halogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, or the plurality of R H s taken together represent a part of an alicyclic structure having 4 to 20 ring atoms constituted together with the carbon chain to which the plurality of R H s bond, and wherein

a sum of m and n is no greater than 16; and

M + is a monovalent radiation-sensitive cation,

in the formula (V-1),

R 1 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms;

R 2 represents a monovalent organic group having 1 to 20 carbon atoms; and

* denotes a binding site to an oxygen atom adjacent to Ar 1 in the formula (1),

in the formula (V-2),

R 3 and R 4 each independently represent a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms;

R 5 represents —O— or —S—; and

R 6 represents a monovalent organic group having 1 to 20 carbon atoms, or

R 4 , R 5 , and R 6 taken together represent a part of a ring structure having 4 to 20 ring atoms constituted together with the atomic chain to which R 4 , R 5 , and R 6 bond; and

* denotes a binding site to an oxygen atom adjacent to Ar 1 in the formula (1), and

in the formula (V-3),

R 7 represents a fluorine atom or a monovalent fluorinated hydrocarbon group having 1 to 20 carbon atoms;

R 8 represents a hydrogen atom, a fluorine atom, or a monovalent organic group having 1 to 20 carbon atoms;

R 9 represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms; and

** denotes a binding site to an oxygen atom adjacent to Ar 1 in the formula (1) or to a part other than the group represented by the formula (V-3) in R G .

9. A compound represented by formula (1):

wherein, in the formula (1),

Ar 1 represents a group obtained by removing (m+n+2) hydrogen atoms from an aromatic ring of an arene having 6 to 30 carbon atoms;

—OH and —COO— are bonded at ortho positions to each other on a same benzene ring on Ar 1 ;

m is an integer of 1 to 16, wherein

in a case in which m is 1, R G represents a group represented by formula (V-1), a group represented by formula (V-2), a group comprising a lactone structure, a group comprising a cyclic carbonate structure, a group comprising a sultone structure, a group comprising a ketonic carbonyl group, a group comprising a thiocarbonate group, or a group comprising a group represented by formula (V-3), and

in a case in which m is no less than 2, a plurality of R G s are identical or different from each other, and each R G represents a group represented by the formula (V-1), a group represented by the formula (V-2), a group comprising a lactone structure, a group comprising a cyclic carbonate structure, a group comprising a sultone structure, a group comprising a ketonic carbonyl group, a group comprising a thiocarbonate group, or a group comprising a group represented by the formula (V-3), or the plurality of R G s taken together represent a part of a ring structure having 5 to 20 ring atoms constituted together with the atomic chain to which the plurality of R G s bond;

n is an integer of 0 to 15, wherein

in a case in which n is 1, R H represents a halogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and

in a case in which n is no less than 2, a plurality of R H s are identical or different from each other, and each R H represents a halogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms, or the plurality of R H s taken together represent a part of an alicyclic structure having 4 to 20 ring atoms constituted together with the carbon chain to which the plurality of R H s bond, and wherein

a sum of m and n is no greater than 16; and

M + is a monovalent radiation-sensitive cation,

in the formula (V-1),

R 1 represents a substituted or unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms;

R 2 represents a monovalent organic group having 1 to 20 carbon atoms; and

* denotes a binding site to an oxygen atom adjacent to Ar 1 in the formula (1),

in the formula (V-2),

R 3 and R 4 each independently represent a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having 1 to 20 carbon atoms;

R 5 represents —O— or —S—; and

R 6 represents a monovalent organic group having 1 to 20 carbon atoms, or

R 4 , R 5 , and R 6 taken together represent a part of a ring structure having 4 to 20 ring atoms constituted together with the atomic chain to which R 4 , R 5 , and R 6 bond; and

* denotes a binding site to an oxygen atom adjacent to Ar 1 in the formula (1), and

in the formula (V-3),

R 7 represents a fluorine atom or a monovalent fluorinated hydrocarbon group having 1 to 20 carbon atoms;

R 8 represents a hydrogen atom, a fluorine atom, or a monovalent organic group having 1 to 20 carbon atoms;

R 9 represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms; and

** denotes a binding site to an oxygen atom adjacent to Ar 1 in the formula (1) or to a part other than the group represented by the formula (V-3) in R G .

10. A method of controlling acid diffusion, comprising:

irradiating a composition which comprises the compound according to claim 9 and an acid generator with a radioactive ray, the acid generator being capable of generating an acid by irradiation with the radioactive ray.