Radiation-sensitive resin composition and resist pattern-forming method
A radiation-sensitive resin composition includes a first compound represented by formula (1), a first polymer comprising an acid-labile group, and a radiation-sensitive acid generator other than the first compound. The radiation-sensitive acid generator includes an onium salt compound. In the formula (1), n is 2 or 3; m is 1 or 2; Y + represents a monovalent radiation-sensitive onium cation; and L represents a single bond or an organic group having a valency of n. L includes linking moieties each linking two of the carboxylate groups in formula (1). Number of atom(s) included in a linking moiety having a minimum number of bonds among the linking moieties is 0 to 10. In a case where L represents a single bond, n is 2, and in a case where n is 2, m is 1.
1. A radiation-sensitive resin composition, comprising:
a first compound represented by formula (1);
a first polymer comprising an acid-labile group and including a structural unit represented by formula (4); and
a radiation-sensitive acid generator other than the first compound, the radiation-sensitive acid generator comprising an onium salt compound,
wherein, in the formula (1):
n is 2 or 3;
m is 1 or 2;
Y + represents a monovalent radiation-sensitive onium cation; and
L represents a single bond or an organic group having a valency of n, and includes linking moieties each linking two of the carboxylate groups in formula (1), number of atom(s) included in a linking moiety having a minimum number of bonds among the linking moieties being 0 to 10,
wherein in a case where L represents a single bond, n is 2, and in a case where n is 2, m is 1,
wherein, in the formula (4):
R 4 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group;
Y′ represents a single bond, a carbonyloxyalkanediyl group having 2 to 20 carbon atoms, a carbonyloxycycloalkanediyl group having 4 to 20 carbon atoms, a carbonyloxycycloalkanediyloxy group having 4 to 20 carbon atoms, an arenediyl group having 6 to 20 carbon atoms or a carbonyloxyarenediyl group having 7 to 20 carbon atoms;
R 5 represents a hydrogen atom, a monovalent chain hydrocarbon group having 1 to 20 carbon atoms, a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms;
R 6 and R 7 each independently represent a monovalent chain hydrocarbon group having 1 to 20 carbon atoms or a monovalent alicyclic hydrocarbon group having 3 to 20 carbon atoms, or R 6 and R 7 taken together represent an alicyclic structure having 3 to 20 ring atoms together with the carbon atom to which R 6 and R 7 bond.
2. The radiation-sensitive resin composition according to claim 1 , further comprising a second polymer having a total percentage content by mass of fluorine atoms and silicon atoms greater than a total percentage content by mass of fluorine atoms and silicon atoms of the first polymer.
3. The radiation-sensitive resin composition according to claim 2 , wherein the second polymer comprises an alkali-labile group.
4. The radiation-sensitive resin composition according to claim 3 , wherein the second polymer comprises a structural unit represented by formula (2):
wherein, in the formula (2), R 1 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an alkoxyalkyl group having 2 to 10 carbon atoms; X represents a divalent organic group having 1 to 20 carbon atoms; and R 2 represents a monovalent hydrocarbon group having 1 to 20 carbon atoms or a monovalent fluorinated hydrocarbon group having 1 to 20 carbon atoms, wherein at least one of X and R 2 represents a group comprising a fluorine atom.
5. The radiation-sensitive resin composition according to claim 1 , wherein L in the formula (1) represents a single bond or a substituted or unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms.
6. The radiation-sensitive resin composition according to claim 1 , wherein L in the formula (1) represents a single bond, or a group comprising 1 or 2 atom(s) in a linking moiety having the minimum number of bonds among the linking moieties each linking two of carboxylate groups.
7. The radiation-sensitive resin composition according to claim 1 , wherein n in the formula (1) is 2, and L represents a substituted or unsubstituted 1,2-benzenediyl group or a substituted or unsubstituted 1,2-ethenediyl group.
8. The radiation-sensitive resin composition according to claim 1 , wherein the first polymer includes a structural unit that includes at least one selected from the group consisting of a lactone structure, a cyclic carbonate structure and a sultone structure.
9. The radiation-sensitive resin composition according to claim 1 , wherein the radiation-sensitive acid generator is included at a content of at least 3 parts by mass with respect to 100 parts by mass of the first polymer.
10. The radiation-sensitive resin composition according to claim 1 , wherein the radiation-sensitive acid generator is included at a content of 3-15 parts by mass with respect to 100 parts by mass of the first polymer.
11. A radiation-sensitive resin composition, comprising:
a first compound represented by formula (1);
a first polymer comprising an acid-labile group; and
a radiation-sensitive acid generator other than the first compound, the radiation-sensitive acid generator comprising an onium salt compound,
wherein, in the formula (1):
n is 2 or 3;
m is 1 or 2;
Y + represents a monovalent radiation-sensitive onium cation; and
L represents a single bond or an organic group having a valency of n, and includes linking moieties each linking two of the carboxylate groups in formula (1), number of atom(s) included in a linking moiety having a minimum number of bonds among the linking moieties being 0 to 10,
wherein in a case where L represents a single bond, n is 2, and in a case where n is 2, m is 1,
wherein the onium salt compound is represented by formula (vi):
R b1 —R b2 —SO 3 − (vi)
wherein, in the formula (vi), R b1 represents a monovalent group comprising an alicyclic structure, or a monovalent group comprising an aliphatic hetero ring structure; R b2 represents a fluorinated alkanediyl group having 1 to 10 carbon atoms; and M + represents a monovalent radioactive ray-degradable onium cation.
12. The radiation-sensitive resin composition according to claim 11 , further comprising a second polymer having a total percentage content by mass of fluorine atoms and silicon atoms greater than a total percentage content by mass of fluorine atoms and silicon atoms of the first polymer.
13. The radiation-sensitive resin composition according to claim 12 , wherein the second polymer comprises an alkali-labile group.
14. The radiation-sensitive resin composition according to claim 13 , wherein the second polymer comprises a structural unit represented by formula (2):
wherein, in the formula (2), R 1 represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms or an alkoxyalkyl group having 2 to 10 carbon atoms; X represents a divalent organic group having 1 to 20 carbon atoms; and R 2 represents a monovalent hydrocarbon group having 1 to 20 carbon atoms or a monovalent fluorinated hydrocarbon group having 1 to 20 carbon atoms, wherein at least one of X and R 2 represents a group comprising a fluorine atom.
15. The radiation-sensitive resin composition according to claim 11 , wherein L in the formula (1) represents a single bond or a substituted or unsubstituted divalent hydrocarbon group having 1 to 20 carbon atoms.
16. The radiation-sensitive resin composition according to claim 11 , wherein L in the formula (1) represents a single bond, or a group comprising 1 or 2 atom(s) in a linking moiety having the minimum number of bonds among the linking moieties each linking two of carboxylate groups.
17. The radiation-sensitive resin composition according to claim 11 , wherein n in the formula (1) is 2, and L represents a substituted or unsubstituted 1,2-benzenediyl group or a substituted or unsubstituted 1,2-ethenediyl group.
18. The radiation-sensitive resin composition according to claim 11 , wherein the first polymer includes a structural unit that includes at least one selected from the group consisting of a lactone structure, a cyclic carbonate structure and a sultone structure.
19. The radiation-sensitive resin composition according to claim 11 , wherein the radiation-sensitive acid generator is included at a content of at least 3 parts by mass with respect to 100 parts by mass of the first polymer.
20. A resist pattern-forming method, comprising:
forming a resist film from a radiation-sensitive resin composition;
exposing the resist film; and
developing the resist film exposed,
wherein the radiation-sensitive resin composition includes
a first compound represented by formula (1),
a first polymer comprising an acid-labile group, and
a radiation-sensitive acid generator other than the first compound, the radiation-sensitive acid generator comprising an onium salt compound,
wherein, in the formula (1):
n is 2 or 3;
m is 1 or 2;
Y + represents a monovalent radiation-sensitive onium cation; and
L represents a single bond or an organic group having a valency of n, and includes linking moieties each linking two of the carboxylate groups in formula (1), number of atom(s) included in a linking moiety having a minimum number of bonds among the linking moieties being 0 to 10,
wherein in a case where L represents a single bond, n is 2, and in a case where n is 2, m is 1.