RADIATION-SENSITIVE RESIN COMPOSITION, METHOD OF FORMING RESIST PATTERN, AND COMPOUND
A radiation-sensitive resin composition includes: a polymer, solubility of which in a developer solution is capable of being altered by an action of an acid; a radiation-sensitive acid generator; and a compound represented by formula (1). Ar 1 represents a group obtained by removing (a+b+2) hydrogen atoms from an aromatic hydrocarbon ring having 6 to 30 ring atoms; R 1 represents a halogen atom or a monovalent organic group having 1 to 20 carbon atoms; L 1 represents a divalent linking group; R 2 represents a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms; a is an integer of 0 to 10, b is an integer of 1 to 10, wherein a sum of a and b is no greater than 10; and X + represents a monovalent radiation-sensitive onium cation.
1 . A radiation-sensitive resin composition comprising:
a polymer, solubility of which in a developer solution is capable of being altered by an action of an acid;
a radiation-sensitive acid generator; and
a compound represented by formula (1):
wherein, in the formula (1),
Ar 1 represents a group obtained by removing (a+b+2) hydrogen atoms from an aromatic hydrocarbon ring having 6 to 30 ring atoms;
R 1 represents a halogen atom or a monovalent organic group having 1 to 20 carbon atoms;
L 1 represents a divalent linking group;
R 2 represents a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms;
a is an integer of 0 to 10; b is an integer of 1 to 10, wherein a sum of a and b is no greater than 10, and wherein in a case in which a is no less than 2, a plurality of R 1 s are identical or different from each other, and wherein in a case in which b is no less than 2, a plurality of L 1 s are identical or different from each other, and a plurality of R 2 s are identical or different from each other; and
X + represents a monovalent radiation-sensitive onium cation.
2 . The radiation-sensitive resin composition according to claim 1 , wherein R 2 in the formula (1) represents a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms in which at least one hydrogen atom on an aromatic ring is substituted with an iodine atom.
3 . The radiation-sensitive resin composition according to claim 1 , wherein L 1 in the formula (1) represents a carbonyloxy group, an oxycarbonyl group, an ether group, a sulfide group, an alkanediyl group having 1 to 5 carbon atoms, or a group being a combination thereof.
4 . The radiation-sensitive resin composition according to claim 1 , wherein the carboxylate group and the hydroxy group in the formula (1) bond to carbon atoms constituting Ar 1 , respectively, the carbon atom to which the carboxylate group bonds and the carbon atom to which the hydroxy group bonds are directly bonded to each other.
5 . The radiation-sensitive resin composition according to claim 1 , wherein the polymer comprises a structural unit comprising an acid-labile group.
6 . The radiation-sensitive resin composition according to claim 5 , wherein the structural unit is represented by formula (2-1) or (2-2):
wherein,
in the formulae (2-1) and (2-2), R 3 represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group; and
Z represents an acid-labile group, and
in the formula (2-2),
L 2 represents a single bond, —COO—, —CONH—, or —O—;
Ar 2 represents a group obtained by removing (s+t+u+1) hydrogen atoms from an aromatic hydrocarbon ring having 6 to 20 ring atoms;
s is an integer of 0 to 10; t is an integer of 0 to 10, wherein a sum of s and t is an integer of 1 to 10, and wherein in a case in which s is no less than 2, a plurality of Zs are identical or different from each other, in a case in which s is no less than 1, R 4 represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and wherein in a case in which t is no less than 2, a plurality of R 4 s are identical or different from each other, in a case in which s is 0 and t is 1, R 4 represents an acid-labile group, and wherein in a case in which s is 0 and t is no less than 2, at least one of a plurality of R 4 s represents an acid-labile group;
R 5 represents a halogen atom or a monovalent organic group having 1 to 20 carbon atoms; and
u is an integer of 0 to 10, wherein in a case in which u is no less than 2, a plurality of R 5 s are identical or different from each other, and wherein a sum of s, t, and u is no greater than 10.
7 . A method of forming a resist pattern, the method comprising:
forming a resist film directly or indirectly on a substrate by applying the radiation-sensitive resin composition according to claim 1 ;
exposing the resist film; and
developing the resist film exposed.
8 . The method according to claim 7 , wherein R 2 in the formula (1) represents a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms in which at least one hydrogen atom on an aromatic ring is substituted with an iodine atom.
9 . The method according to claim 7 , wherein L 1 in the formula (1) represents a carbonyloxy group, an oxycarbonyl group, an ether group, a sulfide group, an alkanediyl group having 1 to 5 carbon atoms, or a group being a combination thereof.
10 . The method according to claim 7 , wherein the carboxylate group and the hydroxy group in the formula (1) bond to carbon atoms constituting Ar 1 , respectively, the carbon atom to which the carboxylate group bonds and the carbon atom to which the hydroxy group bonds are directly bonded to each other.
11 . The method according to claim 7 , wherein the polymer comprises a structural unit comprising an acid-labile group.
12 . The method according to claim 11 , wherein the structural unit is represented by formula (2-1) or (2-2):
wherein,
in the formulae (2-1) and (2-2), R 3 represents a hydrogen atom, a fluorine atom, a methyl group, or a trifluoromethyl group; and
Z represents an acid-labile group, and
in the formula (2-2),
L 2 represents a single bond, —COO—, —CONH—, or —O—;
Ar 2 represents a group obtained by removing (s+t+u+1) hydrogen atoms from an aromatic hydrocarbon ring having 6 to 20 ring atoms;
s is an integer of 0 to 10; t is an integer of 0 to 10, wherein a sum of s and t is an integer of 1 to 10, and wherein in a case in which s is no less than 2, a plurality of Zs are identical or different from each other, in a case in which s is no less than 1, R 4 represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and wherein in a case in which t is no less than 2, a plurality of R 4 s are identical or different from each other, in a case in which s is 0 and t is 1, R 4 represents an acid-labile group, and wherein in a case in which s is 0 and t is no less than 2, at least one of a plurality of R 4 s represents an acid-labile group;
R 5 represents a halogen atom or a monovalent organic group having 1 to 20 carbon atoms; and
u is an integer of 0 to 10, wherein in a case in which u is no less than 2, a plurality of R 5 s are identical or different from each other, and wherein a sum of s, t, and u is no greater than 10.
13 . A compound represented by formula (1):
wherein, in the formula (1),
Ar 1 represents a group obtained by removing (a+b+2) hydrogen atoms from an aromatic hydrocarbon ring having 6 to 30 ring atoms;
R 1 represents a halogen atom or a monovalent organic group having 1 to 20 carbon atoms;
L 1 represents a divalent linking group;
R 2 represents a substituted or unsubstituted monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms;
a is an integer of 0 to 10; b is an integer of 1 to 10, wherein a sum of a and b is no greater than 10, and wherein in a case in which a is no less than 2, a plurality of R 1 s are identical or different from each other, and wherein in a case in which b is no less than 2, a plurality of Lis are identical or different from each other, and a plurality of R 2 s are identical or different from each other; and
X + represents a monovalent radiation-sensitive onium cation.