Resist composition and method for producing resist pattern
Disclosed is a resist composition including a compound represented by formula (I), a resin having an acid-labile group and an acid generator, the resin having an acid-labile group including at least one selected from the group consisting of a structural unit represented by formula (a1-1) and a structural unit represented by formula (a1-2):
1. A resist composition comprising
a compound represented by formula (I),
a resin including at least one selected from the group consisting of a structural unit represented by formula (a1-1) and a structural unit represented by formula (a1-2), and
an acid generator,
wherein, in formula (I),
L 1 represents a single bond or an alkanediyl group having 1 to 6 carbon atoms which may have a substituent,
R 1 represents an acid-labile group represented by formula (1a) or formula (2a),
R 2 represents *-L 1 -OH, *-L 1 -O—R 1 , *—X 1 -Ph-L 1 -OH or *—X 1 -Ph-L 1 -O—R 1 , * represents a bonding site to the benzene ring, and R 1 and R 2 may combine together to form a group having an acetal ring structure,
X 1 represents a single bond, an alkanediyl group having 1 to 6 carbon atoms, —O—, —S—, —SO— or —SO 2 —,
Ph represents a phenylene group which may have a substituent,
m2 represents an integer of 0 to 3, and when m1 is 1 or more, a plurality of L 2 and a plurality of R 1 may be the same or different from each other, and when m2 is 2 or more, a plurality of R 2 may be the same or different from each other,
R 3 represents a halogen atom, an alkyl fluoride group having 1 to 6 carbon atoms or an alkyl group having 1 to 12 carbon atoms, and —CH 2 — included in the alkyl group may be replaced by —O— or —CO—, and
m3 represents an integer of 0 to 5, and when m3 is 2 or more, a plurality of R 3 may be the same or different from each other, in which 0≤m2+m3≤5:
wherein, in formula (1a),
R aa1 represents an alicyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, or R aa1 and R aa2 are bonded to each other to form an alicyclic hydrocarbon group having 3 to 20 carbon atoms together with carbon atoms to which R aa1 and R aa2 are bonded,
R aa2 represents an alkyl group having 1 to 8 carbon atoms which may have a substituent, an alkenyl group having 2 to 8 carbon atoms which may have a substituent, an alicyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, or R aa1 and R aa2 are bonded to each other to form an alicyclic hydrocarbon group having 3 to 20 carbon atoms together with carbon atoms to which R aa1 and R aa2 are bonded,
R aa3 represents an alkyl group having 1 to 8 carbon atoms which may have a substituent, an alkenyl group having 2 to 8 carbon atoms which may have a substituent, an alicyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent,
naa represents 0 or 1, and
* represents a bonding site:
wherein, in formula (2a), R aa1′ and R aa2′ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, R aa3′ represents a hydrocarbon group having 1 to 20 carbon atoms, or R aa2′ and R aa3′ are bonded to each other to form a heterocyclic group having 3 to 20 carbon atoms together with —C—X a — to which R aa2′ and R aa3′ are bonded, and —CH 2 — included in the hydrocarbon group and the heterocyclic group may be replaced by —O— or —S—,
X a represents an oxygen atom or a sulfur atom, and
* represents a bonding site:
wherein, in formula (a1-1) and formula (a1-2):
L a1 and L a2 each independently represent —O— or *—O—(CH 2 ) k1 —CO—O—, k1 represents an integer of 1 to 7, and * represents a bonding site to —CO—,
R a4 and R a5 each independently represent a hydrogen atom, halogen atom or an allyl group having 1 to 6 which may have a halogen atom,
R a6 and R a7 each independently represent an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group obtained by combining these groups,
m1 represents an integer of 0 to 14,
n1 represents an integer of 0 to 10, and
n1′ represents an integer of 0 to 3.
2. The resist composition according to claim 1 , wherein L 1 is a single bond or an alkanediyl group having 1 to 4 carbon atoms which may have a halogen atom.
3. The resist composition according to claim 1 , wherein R 1 is a group represented by formula (1a).
4. The resist composition according to claim 3 , wherein R 1 is a group represented by formula (2a).
5. The resist composition according to claim 4 , wherein R aa2′ and R aa3′ are bonded to each other to form a heterocyclic group having 3 to 8 carbon atoms together with —C—X a — to which R aa2′ and R aa3′ are bonded.
6. The resist composition according to claim 5 , wherein m2 is 1, and R 2 is *-L 1 -OH.
7. The resist composition according to claim 5 , wherein m2 is 1, and R 2 is *-L 1 -O—R 1 .
8. The resist composition according to claim 5 , wherein m2 is 1, and R 2 is *—X 1 -Ph-L 1 -O—R 1 .
9. The resist composition according to claim 1 , wherein m2 is 1.
10. The resist composition according to claim 9 , wherein R 2 is *-L 1 -OH.
11. The resist composition according to claim 10 , wherein m3 is 1 or 2, and R 3 is a halogen atom.
12. The resist composition according to claim 9 , wherein R 2 is *-L 1 -O—R 1 .
13. The resist composition according to claim 12 , wherein m3 is 1 or 2, and R 3 is a halogen atom.
14. The resist composition according to claim 9 , wherein R 2 is *—X 1 -Ph-L 1 -O—R 1 .
15. The resist composition according to claim 1 , wherein m3 is 1 or 2, and R 3 is a halogen atom.
16. The resist composition according to claim 1 , wherein the resin having an acid-labile group further includes a structural unit represented by formula (a2-A):
wherein, in formula (a2-A),
R a50 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom,
R a51 represents a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group or a methacryloyloxy group,
A a50 represents a single bond or * —X a51 -(A a52 -X a52 ) nb — and * represents a bonding site to carbon atoms to which —R a50 is bonded,
A a52 represents an alkanediyl group having 1 to 6 carbon atoms,
X a51 and X a52 each independently represent —O—, —CO—O— or —O—CO—,
nb represents 0 or 1, and
mb represents an integer of 0 to 4, and when mb is an integer of 2 or more, a plurality of R a51 may be the same or different from each other.
17. The resist composition according to claim 1 , wherein the acid generator includes a salt represented by formula (B1):
wherein, in formula (B1),
Q b1 and Q b2 each independently represent a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms,
L b1 represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, —CH 2 — included in the divalent saturated hydrocarbon group may be replaced by —O— or —CO—, and a hydrogen atom included in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group,
Y represents a methyl group which may have a substituent, or an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and —CH 2 — included in the alicyclic hydrocarbon group may be replaced by —O—, —S(O) 2 — or —CO—, and
Z + represents an organic cation.
18. The resist composition according to claim 1 , further comprising a salt generating an acid having an acidity lower than that of an acid generated from the acid generator.
19. The resist composition according to claim 1 , wherein
R 1 and R 2 combine together to form a group having an acetal ring structure.
20. A method for producing a resist pattern, which comprises:
(1) a step of applying the resist composition according to claim 1 on a substrate,
(2) a step of drying the applied composition to form a composition layer,
(3) a step of exposing the composition layer,
(4) a step of heating the exposed composition layer, and
(5) a step of developing the heated composition layer.