Salt, acid generator, resist composition, and method for producing resist pattern

Abstract

To form a resist pattern having good CD uniformity (CDU).SOLUTION: An acid generator contains a salt represented by formula (I).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a salt, an acid generator, a resist composition, and a method for producing a resist pattern. [Background technology]

[0002] Patent Document 1 describes a salt represented by the following formula and a resist composition containing the salt as an acid generator.

[0003] [ka] [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Publication No. 2023-117397 Summary of the Invention [Problem to be solved by the invention]

[0005] There is a need for a technology that can form resist patterns with good CD uniformity (CDU). [Means for solving the problem]

[0006] The present invention includes the following inventions. [Invention 1] An acid generator containing a salt represented by formula (I):

[0007] [ka]

[0008] [In formula (I), Q 1 , Q 2 , R 11 and R 12each independently represents a hydrogen atom, a fluorine atom, an alkyl group having 1 to 6 carbon atoms, or a perfluoroalkyl group having 1 to 6 carbon atoms.

[0009] z represents an integer of 0 to 6, and when z is 2 or greater, the groups in the parentheses may be the same or different. X 1A are -O-, -CO-, -S-, -SO-, -SO2-, -NR 7 - or a group combining these.

[0010] mm1 represents 0 or 1. L 10 represents a single bond or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group is not selected from -O-, -S-, -SO2-, -SO-, -NR 7 It may be replaced by - or -CO-.

[0011] R 7 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. L 1A , L 1B , L 2 and L 3 each independently represents a single bond or an alkanediyl group having 1 to 6 carbon atoms which may have a substituent.

[0012] R 5A and R 5B are each independently -X 1 -R 10 or -X 2 -L 11 -X 1 -R 10 Represents. X 1 is *-CO-O-, *-O-CO-, *-O-CO-O- or *-O- (where * is L 1A Or Ar 1 Binding site with L 1B Or Ar 2 binding site with, or L 11 represents the binding site with .

[0013] X 2 is *-CO-O-, *-O-CO-, *-O-CO-O- or *-O- (where * is L 1A Or Ar 1 binding site with, or L 1B Or Ar 2 represents the binding site with .

[0014] L 11 represents a hydrocarbon group having 1 to 28 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group is not selected from -O-, -S-, -SO2-, -SO-, and -NR 7 It may be replaced by - or -CO-.

[0015] R 10 represents an alicyclic hydrocarbon group having 3 to 36 carbon atoms and having one or more substituents, at least one of which is -OR 11 or a -I group. R 11 represents a hydrogen atom or an acid labile group.

[0016] X 3 are -O-, -CO-, -S-, -SO-, -SO2-, -NR 7 - or a group combining these. Ar 1 and Ar 2 each independently represents an aromatic hydrocarbon group having 6 to 18 carbon atoms.

[0017] R 3 represents a fluorine atom, a fluoroalkyl group having 1 to 6 carbon atoms, an iodine atom, or a hydrocarbon group having 1 to 18 carbon atoms, the hydrocarbon group optionally having a substituent, and -CH2- contained in the hydrocarbon group is -O-, -CO-, -S-, -SO-, -NR 7 It may be replaced by - or -SO2-.

[0018] R 6represents a fluorine atom, a fluorinated alkyl group having 1 to 6 carbon atoms, or a hydrocarbon group having 1 to 18 carbon atoms, the hydrocarbon group optionally having a substituent, and -CH2- contained in the hydrocarbon group is -O-, -CO-, -S-, -SO-, -NR 7 It may be replaced by - or -SO2-.

[0019] m2 represents an integer of 0 to 6, and when m2 is 2 or greater, the groups in the parentheses may be the same or different. 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, and when m2 is 0, R 3 At least one of R represents a fluorine atom or a fluorinated alkyl group having 1 to 6 carbon atoms, or R 3 is an iodine atom, and Ar 1 -L binds to 1A -R 5A or L 10 is bonded through a methylene group.

[0020] m4 and m5 each independently represent an integer of 0 to 5, and when m4 is 2 or greater, the groups in the multiple parentheses may be the same or different from each other, and when m5 is 2 or greater, the groups in the multiple parentheses may be the same or different from each other.

[0021] m6 represents an integer of 0 to 5, and when m6 is 2 or more, a plurality of R 6 may be the same or different from each other. However, 1≦(m2+m4)≦8, 1≦(m3+m6)≦10, and 1≦(m4+m5)≦10.

[0022] Z + represents an organic cation. [Invention 2] L 1A , L 1B , L 2 and L 3and each independently represent a single bond or an alkanediyl group having 1 to 4 carbon atoms which may have one or more halogen atoms.

[0023] [Invention 3] m3 is an integer of 1 or greater, and at least one R 3 is a fluorine atom, an iodine atom, a hydroxy group, a carboxy group, a hydroxyalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a perfluoroalkyl group having 1 to 3 carbon atoms.

[0024] [Invention 4] m6 is an integer equal to or greater than 1, and at least one R 6 4. The acid generator according to any one of inventions 1 to 3, wherein is a fluorine atom, a hydroxy group, a carboxy group, a hydroxyalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a perfluoroalkyl group having 1 to 3 carbon atoms.

[0025] [Invention 5] 5. The acid generator according to any one of inventions 1 to 4, wherein (m2+m4) is 1 or 2. [Invention 6] Ar 1 and Ar 2 and each independently represent an aromatic hydrocarbon group having 6 to 14 carbon atoms.

[0026] [Invention 7] L 10 is a single bond, a chain hydrocarbon group of 1 to 10 carbon atoms which may have a substituent, a cyclic hydrocarbon group of 3 to 24 carbon atoms which may have a substituent, or a group formed by combining a chain hydrocarbon group of 1 to 8 carbon atoms which may have a substituent and a cyclic hydrocarbon group of 3 to 24 carbon atoms which may have a substituent, 7. The acid generator according to any one of inventions 1 to 6, wherein —CH 2 — contained in the chain hydrocarbon group and the cyclic hydrocarbon group may be replaced with —O—, —S—, —SO 2 — or —CO—.

[0027] [Invention 8] R10 is an alicyclic hydrocarbon group having 3 to 12 carbon atoms and having one or more substituents, At least one of the substituents is -OR 11 and R 11 is a hydrogen atom or an acid labile group, 8. The acid generator according to any one of inventions 1 to 7, wherein the acid labile group is a group represented by formula (1a) or a group represented by formula (2a).

[0028] [ka]

[0029] [In formula (1a), R aa1 , R aa2 and R aa3 each independently represents 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 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these, or R aa1 and R aa2 are bonded to each other to form, together with the carbon atoms to which they are bonded, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, and the alkyl group, the alkenyl group, the alicyclic hydrocarbon group and the aromatic hydrocarbon group may have a halogen atom.

[0030] naa represents 0 or 1. * denotes a binding site.]

[0031] [ka]

[0032] [In formula (2a), R aa1′ and R aa2′ each independently represents 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 and they combine -CX aTogether with -, they form a heterocyclic group having 3 to 20 carbon atoms, and -CH2- contained in the hydrocarbon group and the heterocyclic group may be replaced by -O- or -S-, and the hydrocarbon group and the heterocyclic group may have a halogen atom.

[0033] X a represents an oxygen atom or a sulfur atom. * denotes a binding site.] [Invention 9] R 10 is an alicyclic hydrocarbon group having 3 to 12 carbon atoms and having one or more substituents, 9. The acid generator according to any one of Inventions 1 to 8, wherein at least one of the substituents is a -I group.

[0034] [Invention 10] 10. A resist composition containing the acid generator according to any one of Inventions 1 to 9. [Invention 11] Further, the composition contains a resin containing a structural unit having an acid labile group, The resist composition according to invention 10, wherein the structural unit having an acid labile group comprises at least one selected from the group consisting of a structural unit represented by formula (a1-0), a structural unit represented by formula (a1-1), a structural unit represented by formula (a1-2), a structural unit represented by formula (a1-4), a structural unit represented by formula (a1-5), and a structural unit represented by formula (a1-6).

[0035] [ka]

[0036] [In formula (a1-0), formula (a1-1) and formula (a1-2), L a01 , L a1 and L a2 are each independently -O- or -O-(CH2) k1 represents —CO—O—, k1 represents an integer of 1 to 7, and * represents the bonding site with —CO—.

[0037] R a01 , R a4and R a5 each independently represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a02 , R a03 and R a04 each independently represents an alkyl group having 1 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 formed by combining these, and the alkyl group, alicyclic hydrocarbon group, and aromatic hydrocarbon group may contain a halogen atom.

[0038] R a6 and R a7 each independently represents 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 formed by combining these, and the alkyl group, alkenyl group, alicyclic hydrocarbon group, and aromatic hydrocarbon group may contain a halogen atom.

[0039] m1′ represents an integer of 0 to 14. n1 represents an integer of 0 to 10. n1′ represents an integer of 0 to 3.

[0040] [ka]

[0041] [In formula (a1-4), R a1 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom.

[0042] R a17represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, 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.

[0043] A a11 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and -CH2- contained in the alkanediyl group is -O-, -CO- or -NR a18 - may be replaced with

[0044] R a18 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a1 represents a single bond or a carbonyl group. R a34 and R a35 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; R a36 represents a hydrocarbon group having 1 to 20 carbon atoms, or R a35 and R a36 are bonded to each other to form, together with the -CO- to which they are bonded, a divalent hydrocarbon group having 2 to 20 carbon atoms, and the hydrocarbon group and the -CH2- contained in the divalent hydrocarbon group may be replaced with -O- or -S-.

[0045] na1 represents an integer of 1 to 5, and when na1 is 2 or more, the groups in the parentheses may be the same or different. na11 represents an integer of 0 to 4, and when na11 is 2 or more, a plurality of R a17 may be the same or different from each other.

[0046] mc represents an integer between 0 and 2.

[0047] [ka]

[0048] [In formula (a1-5), R a8 represents an alkyl group having 1 to 6 carbon atoms which may have one or more halogen atoms, a hydrogen atom, or a halogen atom.

[0049] Z a1 is a single bond or -(CH2) h3 -CO-L 54 -, h3 represents an integer of 1 to 4, * represents L 51 represents the binding site with L 51 , L 52 , L 53 and L 54 each independently represents -O- or -S-.

[0050] s1 represents an integer of 1 to 3. s1′ represents an integer of 0 to 3.

[0051] [ka]

[0052] [In formula (a1-6), R a61 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom.

[0053] R a62 , R a63 and R a64 each independently represents an alkyl group having 1 to 6 carbon atoms or a cyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent, or R a62 and R a63 are bonded to each other to form a ring having 3 to 20 carbon atoms together with the carbon atoms to which they are attached.

[0054] X a61 is a single bond, -CO-O-* or -CO-NR a65 -*, * represents the binding site with Ar, R a65represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a62 is a single bond, *-OL a61 -or*-CO-OL a62 -, * represents the bonding site with Ar, L a61 and L a62 each independently represents an alkanediyl group having 1 to 4 carbon atoms.

[0055] Ar represents an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent.] [Invention 12] 12. The resist composition according to claim 10 or 11, further comprising a resin containing a structural unit represented by formula (a2-A).

[0056] [ka]

[0057] [In formula (a2-A), R a2 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom.

[0058] R a27 represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, 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.

[0059] A a21 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and -CH2- contained in the alkanediyl group is -O-, -CO- or -NR a28 - may be replaced with

[0060] R a28 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a2 represents a single bond or a carbonyl group. nA2 represents an integer of 1 to 5, and when nA2 is 2 or greater, the groups in the parentheses may be the same or different.

[0061] na21 represents an integer of 0 to 4, and when na21 is 2 or more, a plurality of R a27 may be the same or different from each other. mc represents an integer between 0 and 2. [Invention 13] 13. The resist composition according to any one of inventions 10 to 12, further comprising a salt that generates an acid that is weaker in acidity than the acid generated from the acid generator.

[0062] [Invention 14] (1) a step of applying the resist composition according to any one of inventions 10 to 13 onto a substrate; (2) drying the applied resist composition to form a composition layer; (3) exposing the composition layer to light; (4) heating the composition layer after exposure; and (5) developing the composition layer after heating; A method for producing a resist pattern comprising the steps of:

[0063] [Invention 15] A salt represented by the above formula (I). [Invention 16] L 1A , L 1B , L 2 and L 3 and each independently represent a single bond or an alkanediyl group having 1 to 4 carbon atoms which may have one or more halogen atoms.

[0064] [Invention 17] m3 is an integer of 1 or greater, and at least one R 317. The salt according to invention 15 or 16, wherein is a fluorine atom, an iodine atom, a hydroxy group, a carboxy group, a hydroxyalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a perfluoroalkyl group having 1 to 3 carbon atoms.

[0065] [Invention 18] m6 is an integer equal to or greater than 1, and at least one R 6 18. The salt according to any one of inventions 15 to 17, wherein is a fluorine atom, a hydroxy group, a carboxy group, a hydroxyalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a perfluoroalkyl group having 1 to 3 carbon atoms.

[0066] [Invention 19] 19. The salt according to any one of inventions 15 to 18, wherein (m2+m4) is 1 or 2. [Invention 20] Ar 1 and Ar 2 and each independently represent an aromatic hydrocarbon group having 6 to 14 carbon atoms.

[0067] [Invention 21] L 10 is a single bond, a chain hydrocarbon group of 1 to 10 carbon atoms which may have a substituent, a cyclic hydrocarbon group of 3 to 24 carbon atoms which may have a substituent, or a group formed by combining a chain hydrocarbon group of 1 to 8 carbon atoms which may have a substituent and a cyclic hydrocarbon group of 3 to 24 carbon atoms which may have a substituent, 21. The salt according to any one of inventions 15 to 20, wherein —CH 2 — contained in the chain hydrocarbon group and the cyclic hydrocarbon group may be replaced by —O—, —S—, —SO 2 — or —CO—.

[0068] [Invention 22] R 10 is an alicyclic hydrocarbon group having 3 to 12 carbon atoms and having one or more substituents, At least one of the substituents is -OR 11 and R 11 is a hydrogen atom or an acid labile group, 22. The salt according to any one of inventions 15 to 21, wherein the acid labile group is a group represented by the above formula (1a) or (2a).

[0069] [Invention 23] R 10 is an alicyclic hydrocarbon group having 3 to 12 carbon atoms and having one or more substituents, 23. The salt according to any one of Inventions 15 to 22, wherein at least one of the substituents is a —I group. [Effects of the Invention]

[0070] According to the present invention, resist patterns can be produced with good CD uniformity (CDU). DETAILED DESCRIPTION OF THE INVENTION

[0071] In this specification, "(meth)acrylic monomer" means "at least one of an acrylic monomer and a methacrylic monomer." The terms "(meth)acrylate" and "(meth)acrylic acid" have the same meaning. In the groups described in this specification, those that can have both a linear structure and a branched structure may have either. When -CH2- contained in a hydrocarbon group or the like is -O-, -S-, -CO-, -SO-, -NR XWhen replaced with - (X is any symbol) or -SO2-, the same examples apply to each group, and the number of carbon atoms before replacement is the number of carbon atoms in the hydrocarbon group, etc. "Combined group" refers to a group in which two or more of the exemplified groups are combined, and the valence of these groups may vary appropriately depending on the bonding form. "Derived from" or "derived from" refers to the polymerizable C=C bond contained in the molecule becoming a -CC- group (single bond) through polymerization. If stereoisomers exist, all stereoisomers are included. Depending on the number of substituents, etc., any position and number of hydrogen atoms contained in each group may be substituted for the bonding site. The number of carbon atoms in the substituent is not included in the number of carbon atoms in the substituted group. "Acid labile group" refers to a group in which, upon contact with acid (e.g., trifluoromethanesulfonic acid, etc.), the leaving group is eliminated to form a hydrophilic group (e.g., hydroxy group, carboxy group, etc.). The term "base labile group" refers to a group that, when contacted with a base (e.g., trimethylamine, tetramethylammonium hydroxide, etc.), eliminates the leaving group to form a hydrophilic group (e.g., a carboxy group or a hydroxy group, etc.).

[0072] In this specification, the term "solid content of the resist composition" refers to the sum of all components in the resist composition excluding the solvent (E), which will be described later. <Salt represented by formula (I)> The present invention relates to a salt represented by formula (I) (hereinafter sometimes referred to as "salt (I)").

[0073] In the salt (I), the negatively charged side is sometimes called the "anion (I)" and the positively charged side is sometimes called the "cation (I)". [Anion (I)] In formula (I), Q 1 , Q 2 , R 11 and R 12Examples of the perfluoroalkyl group include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group, a perfluorohexyl group, etc. The number of carbon atoms in the perfluoroalkyl group is preferably 1 to 4, and more preferably 1 to 3.

[0074] Q 1 , Q 2 , R 11 and R 12 Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, etc. The number of carbon atoms in the alkyl group is preferably 1 to 4, and more preferably 1 to 3.

[0075] The salt (I) is preferably, for example, a salt containing a fluorine atom, and Q 1 and Q 2 Preferably, at least one of them contains a fluorine atom or a perfluoroalkyl group, more preferably at least one of them is a fluorine atom or a perfluoroalkyl group, further preferably each is independently a trifluoromethyl group or a fluorine atom, and even more preferably both are fluorine atoms.

[0076] R 11 and R 12 are each independently preferably a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group, more preferably a hydrogen atom or a fluorine atom, and even more preferably a hydrogen atom.

[0077] z is preferably an integer of 0 to 4, more preferably an integer of 0 to 3, even more preferably an integer of 0 to 2, and even more preferably 0 or 1.

[0078] X 1A -O-, -CO-, -NR 7- or a combination thereof is preferred, such as *-CO-O-, *-O-CO-, *-O-, *-O-CO-O-, *-NR 7 -, *-CO-NR 7 -, *-NR 7 -CO-, *-NR 7 -CO-O- or *-O-CO-NR 7 - is more preferred, *-CO-O-, *-O-CO- or *-O-CO-O- is even more preferred, *-CO-O- or *-O-CO- is even more preferred (* is C(R 11 )(R 12 ) or C(Q 1 )(Q 2 ) represents the binding site with ).

[0079] R 7 Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group.

[0080] L 10 Examples of the hydrocarbon group in include linear or branched chain hydrocarbon groups such as alkanediyl groups, monocyclic or polycyclic (including spiro rings, fused rings, or bridged rings) alicyclic hydrocarbon groups, and aromatic hydrocarbon groups, and may also be groups combining two or more of these groups (for example, a hydrocarbon group formed from an alicyclic hydrocarbon group or an aromatic hydrocarbon group and a chain hydrocarbon group). Chain hydrocarbon groups and alicyclic hydrocarbon groups are also referred to as aliphatic hydrocarbon groups, and alicyclic hydrocarbon groups and aromatic hydrocarbon groups are also referred to as cyclic hydrocarbon groups. The hydrocarbon group preferably has 1 to 36 carbon atoms, more preferably 1 to 24, even more preferably 1 to 20, even more preferably 1 to 18, and even more preferably 1 to 12 carbon atoms.

[0081] Examples of the alkanediyl group include linear alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl, nonane-1,9-diyl, decane-1,10-diyl, undecane-1,11-diyl, dodecane-1,12-diyl, tridecane-1,13-diyl, tetradecane-1,14-diyl, pentadecane-1,15-diyl, hexadecane-1,16-diyl, and heptadecane-1,17-diyl groups; Examples of branched alkanediyl groups include ethane-1,1-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-2,2-diyl, pentane-2,4-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl. The terminal of the branched alkanediyl group may be an alkyl group such as a methyl group.

[0082] The chain hydrocarbon group preferably has 1 to 18 carbon atoms, more preferably 1 to 12 carbon atoms, even more preferably 1 to 10 carbon atoms, even more preferably 1 to 8 carbon atoms, still more preferably 1 to 6 carbon atoms, and even more preferably 1 to 4 carbon atoms.

[0083] Examples of the monocyclic or polycyclic alicyclic hydrocarbon group include the following groups: The binding site can be any position.

[0084] [ka]

[0085] Specifically, the alicyclic hydrocarbon group may be a monocyclic divalent alicyclic hydrocarbon group such as a monocyclic cycloalkanediyl group, such as a cyclobutane-1,3-diyl group, a cyclopentane-1,3-diyl group, a cyclohexane-1,4-diyl group, or a cyclooctane-1,5-diyl group; Examples of such divalent alicyclic hydrocarbon groups include cycloalkyl groups such as norbornane-1,4-diyl, norbornane-2,5-diyl, adamantane-1,5-diyl, adamantane-2,6-diyl, spirocyclohexane-1,2'-cyclopentane, and spiroadamantane-2,3'-cyclopentane, and polycyclic cycloalkanediyl groups such as spiro rings each having a cycloalkyl group bonded to a norbornyl or adamantyl group via a spiro bond. The number of carbon atoms in the alicyclic hydrocarbon group may be 3 to 24, preferably 3 to 18, more preferably 3 to 16, and even more preferably 3 to 12.

[0086] Examples of the aromatic hydrocarbon group include arylene groups such as a phenylene group, a naphthylene group, an anthrylene group, a biphenylene group, a phenanthrylene group, etc. The aromatic hydrocarbon group may have 6 to 24 carbon atoms, preferably 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms.

[0087] Examples of groups combining two or more types include a group combining an alicyclic hydrocarbon group with a chain hydrocarbon group, a group combining an aromatic hydrocarbon group with a chain hydrocarbon group, a group combining an alicyclic hydrocarbon group with an aromatic hydrocarbon group, and a group combining an alicyclic hydrocarbon group with a chain hydrocarbon group and an aromatic hydrocarbon group. In the combination, two or more types of alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may each be combined. In addition, when any group is X 1A may be bound to

[0088] Examples of groups combining an alicyclic hydrocarbon group and a chain hydrocarbon group include -divalent alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-divalent alicyclic hydrocarbon group-alkanediyl group-, and -alkanediyl group-divalent alicyclic hydrocarbon group-.

[0089] Examples of groups combining an aromatic hydrocarbon group and a chain hydrocarbon group include -divalent aromatic hydrocarbon group-alkanediyl group-, -alkanediyl group-divalent aromatic hydrocarbon group-alkanediyl group-, and -alkanediyl group-divalent aromatic hydrocarbon group-.

[0090] Examples of groups combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group include -aromatic hydrocarbon group-alicyclic hydrocarbon group-, -alicyclic hydrocarbon group-aromatic hydrocarbon group-, and -alicyclic hydrocarbon group-aromatic hydrocarbon group-alicyclic hydrocarbon group-.

[0091] L 10 -CH2- contained in the hydrocarbon group having 1 to 40 carbon atoms is -O-, -S-, -SO2-, -SO-, -NR 7 It may be replaced by - or -CO-. L 10 The -CH2- contained in the hydrocarbon group having 1 to 40 carbon atoms is -O-, -S-, -SO2-, -SO-, -NR 7 When it is replaced with - or -CO-, the number of carbon atoms before the replacement is regarded as the number of carbon atoms of the hydrocarbon group.

[0092] R 7 Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group.

[0093] The -CH2- contained in the hydrocarbon group can be -O-, -S-, -SO2-, -SO-, or -NR 7 Examples of the group substituted with - or -CO- include a hydroxy group (a group in which -CH2- in a methyl group is replaced with -O-), a carboxy group (a group in which -CH2-CH2- in an ethyl group is replaced with -O-CO-), a thiol group (a group in which -CH2- in a methyl group is replaced with -S-), an amino group (a group in which -CH2- in a methyl group is replaced with -NR 7-), oxy group (a group in which -CH2- in a methylene group is replaced with -O-), carbonyl group (a group in which -CH2- in a methylene group is replaced with -CO-), thio group (a group in which -CH2- in a methylene group is replaced with -S-), sulfonyl group (a group in which -CH2- in a methylene group is replaced with -SO2-), peptide group (a group in which -CH2-CH2- in an ethylene group is replaced with -CO-NR 7 -), alkoxy group (a group in which -CH2- at any position in an alkyl group is replaced with -O-), alkylthio group (a group in which -CH2- at any position in an alkyl group is replaced with -S-), alkylsulfonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -SO2-), alkylamino group (a group in which -CH2- at any position in an alkyl group is replaced with -NR 7 -), alkyl peptide group (wherein -CH2-CH2- at any position in the alkyl group is replaced by -CO-NR 7-), alkoxycarbonyl group (a group in which -CH2-CH2- at any position in an alkyl group is replaced with -O-CO-), alkylcarbonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -CO-), alkylcarbonyloxy group (a group in which -CH2-CH2- at any position in an alkyl group is replaced with -CO-O-), alkoxycarbonyloxy group (a group in which -CH2-CH2-CH2- at any position in an alkyl group is replaced with -O-CO-O-), alkoxyalkoxy group (a group in which two -CH2- at any position in an alkyl group are replaced with -O-), alkanediyloxy group (a group in which -CH2- at any position in an alkanediyl group is replaced with -O- an alkanediyloxycarbonyl group (an alkanediyl group in which -CH2-CH2- at any position is replaced by -O-CO-), an alkanediylcarbonyl group (an alkanediyl group in which -CH2- at any position is replaced by -CO-), an alkanediylcarbonyloxy group (an alkanediyl group in which -CH2-CH2- at any position is replaced by -CO-O-), an alkanediylsulfonyl group (an alkanediyl group in which -CH2- at any position is replaced by -SO2-), an alkanediylthio group (an alkanediyl group in which -CH2- at any position is replaced by -S-), an alkanediylamino group (an alkanediyl group in which -CH2- at any position is replaced by -NR 7 -), alkanediyl peptide group (wherein any -CH2-CH2- at any position in the alkanediyl group is replaced by -CO-NR 7 -substituted), cycloalkoxy groups, cycloalkylalkoxy groups, aromatic hydrocarbon group-carbonyloxy groups, aromatic hydrocarbon group-carbonyl groups, aromatic hydrocarbon group-oxy groups, and groups combining two or more of these groups.

[0094] Examples of the alkoxy group include alkoxy groups having 1 to 39 carbon atoms, such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, and undecyloxy. The number of carbon atoms in the alkoxy group is 1 to 27, and may be 1 to 17, preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3.

[0095] Examples of the alkylthio group include alkylthio groups having 1 to 39 carbon atoms, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, a pentylthio group, a hexylthio group, an octylthio group, a 2-ethylhexylthio group, a nonylthio group, a decylthio group, and an undecylthio group. The number of carbon atoms in the alkylthio group is, for example, 1 to 27, and may be 1 to 17, preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3.

[0096] Examples of the alkylsulfonyl group include alkylsulfonyl groups having 1 to 39 carbon atoms, such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, pentylsulfonyl, hexylsulfonyl, octylsulfonyl, 2-ethylhexylsulfonyl, nonylsulfonyl, decylsulfonyl, and undecylsulfonyl. The alkylsulfonyl group may have 1 to 27 carbon atoms, may be 1 to 17, is preferably 1 to 11, is more preferably 1 to 6, is further preferably 1 to 4, and is further more preferably 1 to 3.

[0097] Examples of the alkylamino group include alkylamino groups having 1 to 39 carbon atoms, such as methylamino, ethylamino, dimethylamino, propylamino, butylamino, pentylamino, and hexylamino. The number of carbon atoms in the alkylamino group is, for example, 1 to 27, and may be 1 to 17, preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3.

[0098] Examples of the alkyl peptide group include alkyl peptide groups having 1 to 39 carbon atoms, such as a methyl peptide group, an ethyl peptide group, a propyl peptide group, etc. The number of carbon atoms in the alkyl peptide group is, for example, 1 to 27, and may be 1 to 17, preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3.

[0099] Examples of alkoxycarbonyl groups include alkoxycarbonyl groups having 2 to 39 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, and a butoxycarbonyl group. Examples of alkylcarbonyl groups include alkylcarbonyl groups having 2 to 40 carbon atoms, such as an acetyl group, a propionyl group, and a butyryl group. Examples of alkylcarbonyloxy groups include alkylcarbonyloxy groups having 2 to 39 carbon atoms, such as an acetyloxy group, a propionyloxy group, and a butyryloxy group. Examples of alkoxycarbonyloxy groups include alkoxycarbonyloxy groups having 2 to 38 carbon atoms, such as a butoxycarbonyloxy group. Examples of alkoxyalkoxy groups include alkoxyalkoxy groups having 2 to 38 carbon atoms, such as a methoxymethoxy group, a methoxyethoxy group, an ethoxymethoxy group, and an ethoxyethoxy group. The alkoxycarbonyl group may have 2 to 27 carbon atoms, and may be 2 to 17, preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. The alkylcarbonyl group may have 2 to 28 carbon atoms, and may be 2 to 18, preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. The alkylcarbonyloxy group may have 2 to 27 carbon atoms, and may be 2 to 17, preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. The alkoxycarbonyloxy group may have 2 to 26 carbon atoms, and may be 2 to 16, preferably 2 to 10, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. The alkoxyalkoxy group may have 2 to 26 carbon atoms, may have 2 to 16 carbon atoms, is preferably 2 to 10 carbon atoms, is more preferably 2 to 6 carbon atoms, is further preferably 2 to 4 carbon atoms, and is further preferably 2 or 3 carbon atoms.

[0100] Examples of the alkanediyloxy group include alkanediyloxy groups having 1 to 39 carbon atoms, such as a methyleneoxy group, an ethyleneoxy group, a propanediyloxy group, a butanediyloxy group, and a pentanediyloxy group. The number of carbon atoms in the alkanediyloxy group is, for example, 1 to 27, and may be 1 to 17, preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3.

[0101] Examples of the alkanediyloxycarbonyl group include alkanediyloxycarbonyl groups having 2 to 39 carbon atoms, such as a methyleneoxycarbonyl group, an ethyleneoxycarbonyl group, a propanediyloxycarbonyl group, and a butanediyloxycarbonyl group. Examples of the alkanediylcarbonyl group include alkanediylcarbonyl groups having 2 to 40 carbon atoms, such as a methylenecarbonyl group, an ethylenecarbonyl group, a propanediylcarbonyl group, a butanediylcarbonyl group, and a pentanediylcarbonyl group. Examples of the alkanediylcarbonyloxy group include alkanediylcarbonyloxy groups having 2 to 39 carbon atoms, such as a methylenecarbonyloxy group, an ethylenecarbonyloxy group, a propanediylcarbonyloxy group, and a butanediylcarbonyloxy group. The number of carbon atoms in the alkanediyloxycarbonyl group is, for example, 2 to 27, and may be 2 to 17, preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. The number of carbon atoms in the alkanediylcarbonyl group is, for example, 2 to 28, and may be 2 to 18, preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. The number of carbon atoms in the alkanediylcarbonyloxy group is, for example, 2 to 27, and may be 2 to 17, preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3.

[0102] Examples of the alkanediylsulfonyl group include alkanediylsulfonyl groups having 1 to 39 carbon atoms, such as a methylenesulfonyl group, an ethylenesulfonyl group, a propylenesulfonyl group, etc. The number of carbon atoms in the alkanediylsulfonyl group is, for example, 1 to 27, and may be 1 to 17, preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3.

[0103] Examples of the alkanediylthio group include alkanediylthio groups having 1 to 39 carbon atoms, such as a methylenethio group, an ethylenethio group, a propylenethio group, etc. The number of carbon atoms in the alkanediylthio group is, for example, 1 to 27, and may be 1 to 17, preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3.

[0104] Examples of the alkanediylamino group include alkanediylamino groups having 1 to 39 carbon atoms, such as a methyleneamino group, an ethyleneamino group, a dimethyleneamino group, a propyleneamino group, a butyleneamino group, a pentyleneamino group, and a hexyleneamino group. The number of carbon atoms in the alkanediylamino group is, for example, 1 to 27, and may be 1 to 17, preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3.

[0105] Examples of the alkanediyl peptide group include alkanediyl peptide groups having 1 to 39 carbon atoms, such as a methylene peptide group, an ethylene peptide group, a propylene peptide group, etc. The number of carbon atoms in the alkanediyl peptide group is, for example, 1 to 27, and may be 1 to 17, preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3.

[0106] Examples of cycloalkoxy groups include cycloalkoxy groups having 3 to 39 carbon atoms, such as a cyclohexyloxy group. Examples of cycloalkylalkoxy groups include cycloalkylalkoxy groups having 4 to 39 carbon atoms, such as a cyclohexylmethoxy group. Examples of aromatic hydrocarbon group-carbonyloxy groups include aromatic hydrocarbon group-carbonyloxy groups having 7 to 39 carbon atoms, such as a benzoyloxy group. Examples of aromatic hydrocarbon group-carbonyl groups include aromatic hydrocarbon group-carbonyl groups having 7 to 40 carbon atoms, such as a benzoyl group. Examples of aromatic hydrocarbon group-oxy groups include aromatic hydrocarbon group-oxy groups having 6 to 39 carbon atoms, such as a phenyloxy group.

[0107] In addition, -CH2- contained in an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a group combining these may be -O-, -S-, -CO-, -SO-, -NR 7 Examples of groups substituted with - or -SO2- include the following groups: -O- or -CO- in the groups shown below are -S-, -SO-, and -NR 7 The binding site can be at any position.

[0108] [ka]

[0109] L 10 Examples of the substituent that may be possessed by L include a halogen atom, a cyano group, and a nitro group. 10 However, in the case of a group in which an alicyclic hydrocarbon group or an aromatic hydrocarbon group is combined with a chain hydrocarbon group such as an alkyl group, the chain hydrocarbon group such as an alkyl group can be substantially used as a substituent of the alicyclic hydrocarbon group or the aromatic hydrocarbon group. 10 The -CH2- contained in the chain hydrocarbon group such as the alkyl group contained in 7 - or -SO2-, L 10can substantially have a substituent such as a hydroxy group, a carboxy group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, an alkoxycarbonyloxy group, an alkoxyalkoxy group, an alkylamino group, an amino group, a thiol group, an alkylthio group, an alkylsulfonyl group, or an alkylpeptide group. 7 The groups substituted with - or -SO2- include the same groups as those exemplified in this specification, within the upper limit of the carbon number.

[0110] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. L 10 The substituent in is preferably an alkyl group having 1 to 4 carbon atoms, a hydroxy group or a halogen atom, more preferably an alkyl group having 1 to 4 carbon atoms or a halogen atom, and further preferably a methyl group or a fluorine atom.

[0111] L 10 The alkyl group may be a single bond, a chain hydrocarbon group having 1 to 12 carbon atoms which may have a substituent (-CH2- contained in the chain hydrocarbon group may be -O-, -S-, -SO2-, -SO-, -NR 7 - or -CO-), a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent (-CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO2-, -SO-, -NR 7 - or -CO-) or a group in which a chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent is combined with a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent (the -CH2- contained in the chain hydrocarbon group and the cyclic hydrocarbon group may be replaced with -O-, -S-, -SO2-, -SO-, -NR 7- or -CO-), and examples thereof include a single bond, a chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent (-CH2- contained in the chain hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-), a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, or a group combining a chain hydrocarbon group having 1 to 8 carbon atoms which may have a substituent and a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent (-CH2- contained in the chain hydrocarbon group and the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-). , -O-, -S-, -SO2- or -CO-), and is preferably a single bond, an alkanediyl group having 1 to 8 carbon atoms which may have a substituent (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), an alicyclic hydrocarbon group having 5 to 12 carbon atoms which may have a substituent (-CH2- contained in the alicyclic hydrocarbon group may be replaced with -O- or -CO-), an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, a group in which an alkanediyl group having 1 to 6 carbon atoms which may have a substituent is combined with an alicyclic hydrocarbon group having 5 to 12 carbon atoms which may have a substituent (-CH2- contained in the alkanediyl group and the alicyclic hydrocarbon group may be replaced with -O- or -CO-), or a group in which an alkanediyl group having 1 to 6 carbon atoms which may have a substituent is combined with an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent (-CH2- contained in the alkanediyl group and the alicyclic hydrocarbon group may be replaced with -O- or -CO-). 2- may be replaced by -O- or -CO-), and a single bond, a methylene group, -CH-O-, -adamantanediyl group -CO-O-, -CH-adamantanediyl group -O-CO-, -norbornanelactonediyl group -CO-O-, -optionally substituted phenylene group -CO-O-, -optionally substituted phenylene group -O-CO- or -optionally substituted phenylene group -O-CO-O- is even more preferred.

[0112] Also, L 10 is a single bond, *-L 12 -or*-L 12 -X 13 -L 13 -(L 12represents an alkanediyl group having 1 to 8 carbon atoms or a group in which an alkanediyl group having 1 to 3 carbon atoms is combined with an alicyclic hydrocarbon group having 5 to 12 carbon atoms, and -CH2- contained in the alkanediyl group and the alicyclic hydrocarbon group may be replaced with -O- or -CO-. * represents X 1A X represents the binding site. 13 represents **-CO-O-, **-O-CO-, **-O-CO-O- or **-O-, and ** represents L 12 It represents the binding site with L 13 represents a single bond or an alkanediyl group having 1 to 3 carbon atoms.) is also preferred.

[0113] L 12 The alicyclic hydrocarbon group of L 10 Examples of the groups include the same as those exemplified in L 12 and L 13 The alkanediyl group of L 10 Examples of the groups include the same as those exemplified in

[0114] L 12 is preferably an alkanediyl group having 1 to 3 carbon atoms or a group in which an alkanediyl group having 1 to 2 carbon atoms is combined with an alicyclic hydrocarbon group having 6 to 12 carbon atoms (-CH2- contained in the alkanediyl group and the alicyclic hydrocarbon group may be replaced with -O- or -CO-). 13 is preferably **-CO-O- or **-O-CO-. 13 is preferably a single bond or an alkanediyl group having 1 to 2 carbon atoms.

[0115] R 5A and R 5B X included in 1 are each independently preferably *-CO-O-, *-O-CO- or *-O-CO-O-, more preferably *-CO-O- or *-O-CO-O- (* represents L 1A Or Ar 1 binding site with, or L 1B Or Ar 2 binding site with, or L11 represents the binding site with ).

[0116] R 5A and R 5B L included in 11 The hydrocarbon groups in each of the above may be independently selected within the range permitted by the upper limit of the number of carbon atoms. 10 Examples of the hydrocarbon groups include the same hydrocarbon groups as those listed in L 11 The substituents that the hydrocarbon group may have are also 10 The substituents that may be contained in the hydrocarbon group of L are the same as those that may be contained in the hydrocarbon group of L. 11 The -CH2- contained in the hydrocarbon group is -O-, -S-, -SO2-, -SO-, -NR 7 The group substituted with - or -CO- is also 10 The -CH2- contained in the hydrocarbon group is -O-, -S-, -SO2-, -SO-, -NR 7 The hydrocarbon group preferably has 1 to 24 carbon atoms, more preferably 1 to 20 carbon atoms, even more preferably 1 to 18 carbon atoms, still more preferably 1 to 12 carbon atoms, even more preferably 1 to 10 carbon atoms, still more preferably 1 to 8 carbon atoms, and still more preferably 1 to 6 carbon atoms.

[0117] L 11 The alkyl group may be a chain hydrocarbon group having 1 to 12 carbon atoms (the chain hydrocarbon group may have a substituent). The —CH— contained in the chain hydrocarbon group may be —O—, —S—, —SO—, —SO—, —NR 7 - or -CO-) or a group in which a chain hydrocarbon group having 1 to 6 carbon atoms is combined with an alicyclic hydrocarbon group having 3 to 18 carbon atoms (the chain hydrocarbon group and the alicyclic hydrocarbon group may have a substituent. -CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, -S-, -SO2-, -SO-, -NR 7- or -CO-), more preferably an alkanediyl group having 1 to 10 carbon atoms (the alkanediyl group may have a substituent. -CH2- contained in the alkanediyl group may be replaced with -O- or -CO-) or a group combining an alkanediyl group having 1 to 4 carbon atoms with an alicyclic hydrocarbon group having 3 to 12 carbon atoms (the alkanediyl group and the alicyclic hydrocarbon group may have a substituent. -CH2- contained in the alkanediyl group and the alicyclic hydrocarbon group may be replaced with -O- or -CO-), even more preferably an alkanediyl group having 1 to 6 carbon atoms, even more preferably an alkanediyl group having 1 to 3 carbon atoms, and even more preferably a methylene group.

[0118] R 5A and R 5B X included in 2 are each independently preferably *-CO-O-, *-O-CO-O- or *-O-, more preferably *-CO-O- or *-O- (* represents L 1A Or Ar 1 binding site with, or L 1B Or Ar 2 represents the binding site with ).

[0119] R 5A and R 5B R included in 10 The alicyclic hydrocarbon group having 3 to 36 carbon atoms may be either monocyclic or polycyclic. Specific examples of the alicyclic hydrocarbon group include the groups shown below: The bonding site can be at any position.

[0120] [ka]

[0121] Examples of monocyclic alicyclic hydrocarbon groups include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and cyclodecyl. Examples of polycyclic alicyclic hydrocarbon groups include cycloalkyl groups having 5 to 8 carbon atoms, such as decahydronaphthyl, adamantyl, norbornyl, spirocyclohexane-1,2'-cyclopentane, and spiroadamantane-2,3'-cyclopentane, and polycyclic cycloalkyl groups such as spiro rings having cycloalkyl groups having 5 to 8 carbon atoms bonded to a norbornyl or adamantyl group via a spiro bond. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 24, more preferably 3 to 18, even more preferably 3 to 16, and even more preferably 3 to 12. R 10 Among these, the alicyclic hydrocarbon group is preferably an alicyclic hydrocarbon group having 3 to 18 carbon atoms, more preferably an alicyclic hydrocarbon group having 3 to 12 carbon atoms, still more preferably a cyclohexyl group, a norbornyl group, or an adamantyl group, and even more preferably an adamantyl group.

[0122] R 11 The acid labile group in R 11 When a group represented by the following formula (I) is eliminated, it forms a carboxy group or a hydroxy group. The acid labile group is preferably a group represented by formula (1a) (hereinafter sometimes referred to as "acid labile group (1a)") or a group represented by formula (2a) (hereinafter sometimes referred to as "acid labile group (2a)").

[0123] [ka]

[0124] [In formula (1a), R aa1 , R aa2 and R aa3each independently represents 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 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these, or R aa1 and R aa2 are bonded to each other to form, together with the carbon atoms to which they are bonded, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, and the alkyl group, the alkenyl group, the alicyclic hydrocarbon group and the aromatic hydrocarbon group may have a halogen atom.

[0125] naa represents 0 or 1. * denotes a binding site.]

[0126] [ka]

[0127] [In formula (2a), R aa1′ and R aa2′ each independently represents 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 and they combine -CX a Together with -, they form a heterocyclic group having 3 to 20 carbon atoms, and -CH2- contained in the hydrocarbon group and the heterocyclic group may be replaced by -O- or -S-, and the hydrocarbon group and the heterocyclic group may have a halogen atom.

[0128] X a represents an oxygen atom or a sulfur atom. * denotes a binding site.] R aa1 , R aa2 and R aa3 Examples of the alkyl group of R include a methyl group, an ethyl group, a propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, and an n-octyl group. aa1 , R aa2 and R aa3The alkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms, and even more preferably 1 to 3 carbon atoms.

[0129] R aa1 , R aa2 and R aa3 Examples of the alkenyl group include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups.

[0130] R aa1 , R aa2 and R aa3 The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of polycyclic alicyclic hydrocarbon groups include decahydronaphthyl, adamantyl, and norbornyl groups, as well as the following groups (where * indicates a bonding site): aa1 , R aa2 and R aa3 The alicyclic hydrocarbon group preferably has 3 to 16 carbon atoms, and more preferably 3 to 12 carbon atoms.

[0131] [ka]

[0132] R aa1 , R aa2 and R aa3 Examples of the aromatic hydrocarbon group of R include aryl groups such as phenyl, naphthyl, anthryl, biphenyl, and phenanthryl. aa1 , R aa2 and R aa3 The aromatic hydrocarbon group preferably has 6 to 14 carbon atoms, and more preferably 6 to 10 carbon atoms.

[0133] Examples of the combined group include a group in which the above-mentioned alkyl group and alicyclic hydrocarbon group are combined (for example, an alkylcycloalkyl group or cycloalkylalkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, a methylnorbornyl group, a cyclohexylmethyl group, an adamantylmethyl group, an adamantyldimethyl group, or a norbornylethyl group), an aralkyl group such as a benzyl group, an aromatic hydrocarbon group having an alkyl group (a p-methylphenyl group, a p-tert-butylphenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a 2,6-diethylphenyl group, a 2-methyl-6-ethylphenyl group, or the like), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (a p-cyclohexylphenyl group, a p-adamantylphenyl group, or the like), and an aryl-cycloalkyl group such as a phenylcyclohexyl group.

[0134] naa is preferably 1. R aa1 and R aa2 -C(R aa1 )(R aa2 )(R aa3 ) includes the following groups. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 16, more preferably 3 to 12. * represents a bonding site.

[0135] [ka]

[0136] The group represented by formula (1a) includes a 1,1,1-trialkyl group, a 1,1,1-trialkylalkoxycarbonyl group (in formula (1a), R aa1 , R aa2 and R aa3 is an alkyl group, preferably a tert-butyl group or a tert-butoxycarbonyl group), a 2-alkyladamantan-2-yl group, a 2-alkyladamantan-2-yloxycarbonyl group (in formula (1a), R aa1 , R aa2and the carbon atoms to which they are bonded form an adamantyl group, and R aa3 is an alkyl group), and 1-(adamantan-1-yl)-1,1-dialkyl groups, 1-(adamantan-1-yl)-1,1-dialkylalkoxycarbonyl groups (in formula (1a), R aa1 and R aa2 is an alkyl group, and R aa3 is an adamantyl group).

[0137] R aa1′ , R aa2′ and R aa3′ Examples of the hydrocarbon group include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these groups.

[0138] Alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups and combination groups are R aa1 , R aa2 and R aa3 Examples of the groups include the same groups as those listed in the above. R aa2′ and R aa3′ are bonded to each other and the carbon atoms to which they are bonded and X a When forming a heterocyclic group together with -C(R aa1′ )(R aa2′ )-X a -(R aa3′ ) includes the following groups: * represents a binding site.

[0139] [ka]

[0140] R aa1′ and R aa2′ At least one of these is preferably a hydrogen atom. R aa1 , R aa2 , R aa3 , R aa1′ , R aa2′ and R aa3′The halogen atom that may be contained in the ring may be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0141] Specific examples of the acid labile group (1a) include the following groups: * represents a bonding site.

[0142] [ka]

[0143] Specific examples of the acid labile group (2a) include the following groups: * represents a bonding site.

[0144] [ka]

[0145] R 11 is preferably a hydrogen atom or an acid labile group (2a). R 10 The alicyclic hydrocarbon group has -OR 11 The number of -I groups is at least 1, and preferably 1 or 2. 10 The alicyclic hydrocarbon group is -OR 11 R may have both the -I and -I groups as substituents. 10 The alicyclic hydrocarbon group is -OR 11 Alternatively, it may have a substituent other than -I, and examples thereof include an alkyl group having 1 to 3 carbon atoms, a fluorine atom, and a fluorinated alkyl group having 1 to 3 carbon atoms.

[0146] R 10 The group represented by the formula: 11 an alicyclic hydrocarbon group having 3 to 12 carbon atoms, 11 and an alicyclic hydrocarbon group having 3 to 12 carbon atoms and one or two iodine atoms (the alicyclic hydrocarbon group may have a substituent other than the -I group), and one or two -OR 11a polycyclic alicyclic hydrocarbon group having 6 to 12 carbon atoms, 11 and the alkyl group is more preferably a C6 to C12 polycyclic alicyclic hydrocarbon group having one or two iodine atoms (the polycyclic alicyclic hydrocarbon group may have a substituent other than the -I group), and more preferably a C6 to C12 polycyclic alicyclic hydrocarbon group having one or two iodine atoms (the polycyclic alicyclic hydrocarbon group may have a substituent other than the -I group), and 11 or an adamantyl group having one or two iodine atoms, and an adamantyl group having one or two hydroxy groups, one -OR 11A (R 11A represents an acid labile group represented by formula (1a) or formula (2a). 11B (R 11B represents an acid labile group represented by formula (2a). It is even more preferred that the adamantyl group has one or two -I groups.

[0147] R 5A and R 5B are each independently -OR 10 , -CO-OR 10 , -O-CO-OR 10 , -O-CO-R 10 or -OL 11 -CO-OR 10 It is preferable that:

[0148] Ar 1 and Ar 2Examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms include a group derived from a benzene ring, a group derived from a naphthalene ring, a group derived from an anthracene ring, a group derived from an indene ring, a group derived from a phenanthrene ring, a group derived from a fluorene ring, or a group derived from a diphenylmethane ring, and the like, with a group derived from a benzene ring, a group derived from a naphthalene ring, or a group derived from a diphenylmethane ring being preferred, and a group derived from a benzene ring being more preferred. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 16, more preferably 6 to 14, and even more preferably 6 to 10.

[0149] L 1A , L 1B , L 2 and L 3 Examples of the alkanediyl group in the formula (I) include linear alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl; and Examples of branched alkanediyl groups include ethane-1,1-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-2,2-diyl, pentane-2,4-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl. The alkanediyl group preferably has 1 to 4 carbon atoms, and more preferably 1 to 3 carbon atoms.

[0150] L 1A , L 1B , L 2 and L 3 Examples of the substituent that the alkanediyl group may have include a halogen atom, a hydroxy group, a cyano group, a nitro group, a carboxy group, an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, and a group formed by combining two or more of these groups.

[0151] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the alkyl group having 1 to 12 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group, a nonyl group, etc. The number of carbon atoms in the alkyl group is preferably 1 to 9, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3.

[0152] The haloalkyl group having 1 to 6 carbon atoms represents an alkyl group having a halogen atom, and examples thereof include a fluorinated alkyl group, a chlorinated alkyl group, a brominated alkyl group, and an iodinated alkyl group. Examples of the haloalkyl group include a trifluoromethyl group, a difluoromethyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, and an iodomethyl group. The number of carbon atoms in the haloalkyl group is preferably 1 to 4, and more preferably 1 to 3.

[0153] Examples of the alkoxy group having 1 to 12 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, a dodecyloxy group, etc. The number of carbon atoms in the alkoxy group is preferably 1 to 9, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3.

[0154] Examples of groups that combine two or more types include an alkoxycarbonyl group having 2 to 13 carbon atoms, an alkylcarbonyl group having 2 to 13 carbon atoms, and an alkylcarbonyloxy group having 2 to 13 carbon atoms.

[0155] The alkoxycarbonyl group having 2 to 13 carbon atoms, the alkylcarbonyl group having 2 to 13 carbon atoms, and the alkylcarbonyloxy group having 2 to 13 carbon atoms represent groups in which a carbonyl group or a carbonyloxy group is bonded to the above-mentioned alkyl group or alkoxy group.

[0156] Examples of the alkoxycarbonyl group having 2 to 13 carbon atoms include a methoxycarbonyl group, an ethoxycarbonyl group, and a butoxycarbonyl group. Examples of the alkylcarbonyl group having 2 to 13 carbon atoms include an acetyl group, a propionyl group, and a butyryl group. Examples of the alkylcarbonyloxy group having 2 to 13 carbon atoms include an acetyloxy group, a propionyloxy group, and a butyryloxy group.

[0157] L 1A , L 1B , L 2 and L 3 is preferably a single bond or an alkanediyl group having 1 to 4 carbon atoms which may have a substituent, more preferably a single bond or an alkanediyl group having 1 to 4 carbon atoms which may have a halogen atom, even more preferably a single bond or an alkanediyl group having 1 to 4 carbon atoms which may have a fluorine atom, still more preferably a single bond or an alkanediyl group having 1 to 3 carbon atoms, and even more preferably a single bond or a methylene group.

[0158] L 1A Ar 1 The bonding position to Ar is not particularly limited. 1 When is a group derived from a benzene ring, L 10 It is preferable that the bond is at the o- or p-position relative to the bonding position of Ar 1 When is a group derived from a naphthalene ring, L 10 But, Ar 1 When the compound is bonded to the 1st or 2nd position of Ar 1 Preferably, m2=0 and at least one R 3 is an iodine atom, L 1A The bonding position of L 10is preferably a carbon atom adjacent to the carbon atom to which it is bonded.

[0159] L 1B Ar 2 The bonding position to Ar is not particularly limited. 2 When is a group derived from a benzene ring, L 3 It is preferable that the bond is m- or p-position relative to the bonding position of Ar 1 When is a group derived from a naphthalene ring, L 10 But, Ar 1 When the compound is bonded to the 1st or 2nd position of Ar 1 It is preferred that the aryl group is bonded to the 3rd, 4th, 5th, 6th or 7th position of the aryl group.

[0160] L 2 Ar 1 The bonding position to Ar is not particularly limited. 1 When is a group derived from a benzene ring, L 10 It is preferable that the bond is at the o- or p-position relative to the bonding position of Ar 1 When is a group derived from a naphthalene ring, L 10 But, Ar 1 When the compound is bonded to the 1st or 2nd position of Ar 1 It is preferred that the aryl group is bonded to the 3rd, 4th, 5th, 6th or 7th position of the aryl group.

[0161] X 3 -O-, -CO-, -NR 7 - or a combination thereof is preferred, such as *-CO-O-, *-O-CO-, *-O-CO-O-, *-O-, *-NR 7 -, *-CO-NR 7 -, *-NR 7 -CO-, *-NR 7 -CO-O- or *-O-CO-NR 7 - is more preferred, *-CO-O-, *-O-CO-, *-O-CO-O- or *-O- is even more preferred, *-CO-O-, *-O-CO- or *-O-CO-O- is even more preferred, *-CO-O- or *-O-CO- is even more preferred (* is L2 or Ar 1 represents the binding site with ).

[0162] m2 is preferably an integer of 0 to 5, more preferably an integer of 0 to 4, even more preferably an integer of 0 to 3, even more preferably an integer of 0 to 2, and even more preferably 0 or 1.

[0163] m4 is preferably an integer of 0 to 4, more preferably an integer of 0 to 3, still more preferably an integer of 0 to 2, and even more preferably 0 or 1.

[0164] m5 is preferably an integer of 0 to 4, more preferably an integer of 1 to 4, even more preferably an integer of 1 to 3, and even more preferably 1 or 2.

[0165] m2+m4 is preferably an integer of 0 to 6, more preferably an integer of 1 to 6, even more preferably an integer of 1 to 4, and even more preferably 1 or 2.

[0166] m4+m5 is preferably an integer of 1 to 9, and more preferably an integer of 1 to 8. R 3 and R 6 The fluorinated alkyl group having 1 to 6 carbon atoms refers to an alkyl group having 1 to 6 carbon atoms and a fluorine atom. Examples of the fluorinated alkyl group include perfluoroalkyl groups having 1 to 6 carbon atoms (such as trifluoromethyl, pentafluoroethyl, heptafluoropropyl, and nonafluorobutyl), 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, and 3,3,4,4,4-pentafluorobutyl. The number of carbon atoms in the fluorinated alkyl group is preferably 1 to 4, more preferably 1 to 3, even more preferably 1 or 2, and even more preferably 1.

[0167] R 3 and R 6 Examples of the hydrocarbon group having 1 to 18 carbon atoms include chain hydrocarbon groups such as alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these. The number of carbon atoms in the hydrocarbon group is preferably 1 to 16, more preferably 1 to 12, even more preferably 1 to 10, still more preferably 1 to 8, and even more preferably 1 to 6.

[0168] The alkyl group is a linear or branched alkyl group, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, a 2-ethylhexyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, and a dodecyl group. The number of carbon atoms in the linear hydrocarbon group is preferably 1 to 12, more preferably 1 to 9, even more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0169] The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and examples thereof include the groups shown below: The bonding site may be at any position.

[0170] [ka]

[0171] Specifically, examples of monocyclic alicyclic hydrocarbon groups include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and cyclodecyl. Examples of polycyclic alicyclic hydrocarbon groups include cycloalkyl groups such as decahydronaphthyl, adamantyl, norbornyl, spirocyclohexane-1,2'-cyclopentane, and spiroadamantane-2,3'-cyclopentane, as well as polycyclic cycloalkyl groups such as spiro rings having cycloalkyl groups bonded to norbornyl or adamantyl groups via spiro bonds. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 18, more preferably 3 to 16, and even more preferably 3 to 12.

[0172] Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a phenanthryl group, a binaphthyl group, etc. The aromatic hydrocarbon group preferably has 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms.

[0173] Examples of groups formed by combining these groups include groups combining an aromatic hydrocarbon group with a chain hydrocarbon group (e.g., aromatic hydrocarbon group-alkanediyl group-*, alkyl group-aromatic hydrocarbon group-*, alkyl group-aromatic hydrocarbon group-alkanediyl group-*), groups combining an alicyclic hydrocarbon group with a chain hydrocarbon group (e.g., alicyclic hydrocarbon group-alkanediyl group-*, alkyl group-alicyclic hydrocarbon group-*, alkyl group-alicyclic hydrocarbon group-alkanediyl group-*), and groups combining an aromatic hydrocarbon group with a alicyclic hydrocarbon group (e.g., aromatic hydrocarbon group-alicyclic hydrocarbon group-*, alicyclic hydrocarbon group-aromatic hydrocarbon group-*). * represents a bonding site. In each of the above groups, -CH2- contained in the alkyl group, the alkanediyl group, and the alicyclic hydrocarbon group may be -O-, -CO-, -S-, -SO-, -NR 7 It may be replaced by - or -SO2-.

[0174] The aromatic hydrocarbon group -alkanediyl group-* includes aralkyl groups such as benzyl group and phenethyl group. Examples of the alkyl group-aromatic hydrocarbon group-* include a tolyl group, a xylyl group, and a cumenyl group.

[0175] Examples of the alicyclic hydrocarbon group -alkanediyl group-* include cycloalkylalkyl groups such as a cyclohexylmethyl group, a cyclohexylethyl group, a 1-(adamantan-1-yl)methyl group, and a 1-(adamantan-1-yl)-1-methylethyl group.

[0176] Examples of the alkyl group-alicyclic hydrocarbon group-* include cycloalkyl groups having an alkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, and a 2-alkyladamantan-2-yl group.

[0177] Examples of the aromatic hydrocarbon group-alicyclic hydrocarbon group-* include a phenylcyclohexyl group. Examples of the alicyclic hydrocarbon group-aromatic hydrocarbon group-* include a cyclohexylphenyl group.

[0178] In addition, in the combination, two or more types of alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may be combined. 1 or Ar 2 may be bound to

[0179] R 3 and R 6 -CH2- contained in the hydrocarbon group represented by the formula: 7 When the hydrocarbon group is substituted with - or -SO2-, the number of carbon atoms before the substitution is taken as the total number of carbon atoms in the hydrocarbon group.

[0180] The -CH2- contained in the hydrocarbon group can be -O-, -S-, -SO2-, -SO-, or -NR 7Examples of groups substituted for - or -CO- include a hydroxyl group, a thiol group, a carboxyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkoxycarbonyloxy group, an alkoxyalkoxy group, an alkylthio group, an alkylsulfonyl group, an oxy group, a carbonyl group, a thio group, a sulfonyl group, an alkanediyloxy group, an alkanediyloxycarbonyl group, an alkanediylcarbonyl group, an alkanediylcarbonyloxy group, an alkanediylthio group, an alkanediylsulfonyl group, an amino group, a peptide group, an alkylamino group, an alkylpeptide group, an alkanediylamino group, an alkanediylpeptide group, a cycloalkoxy group, a cycloalkylalkoxy group, an aromatic hydrocarbon group-carbonyloxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy group, and a group combining two or more of these groups. These substituted groups include the same groups as those exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms. The number of carbon atoms in these substituted groups is, for example, 1 to 17 in the case of an alkoxy group or the like, preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3; 2 to 17 in the case of an alkoxycarbonyl group or the like, preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3; 2 to 18 in the case of an alkylcarbonyl group or the like, preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3; and 2 to 16 in the case of an alkoxycarbonyloxy group or the like, preferably 2 to 10, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3.

[0181] In addition, -CH2- contained in an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a group combining these may be -O-, -S-, -SO2-, -SO-, -NR 7 Examples of the group substituted with - or -CO- include the same groups as those exemplified in this specification, within the upper limit of the carbon number.

[0182] R 3 and R 6 Examples of the substituent that the hydrocarbon group may have include a halogen atom, a cyano group, and a nitro group. 3 and R 6 In the case of a group in which an alicyclic hydrocarbon group or an aromatic hydrocarbon group is combined with a chain hydrocarbon group such as an alkyl group, the chain hydrocarbon group such as an alkyl group can be substantially a substituent of the alicyclic hydrocarbon group or the aromatic hydrocarbon group. 3 and R 6 The -CH2- contained in the chain hydrocarbon group such as the alkyl group contained in 7 - or -SO2-, R 3 and R 6 can substantially have a substituent such as a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkoxycarbonyloxy group, an alkoxyalkoxy group, a thiol group, an alkylthio group, an alkylsulfonyl group, an amino group, an alkylamino group, or an alkylpeptide group.

[0183] Examples of the halogen atom include the same groups as those mentioned above. R 3is preferably an iodine atom, a fluorine atom, a fluorinated alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 8 carbon atoms (wherein —CH— in the alkyl group may be replaced with —O— or —CO—), more preferably an iodine atom, a fluorine atom, a fluorinated alkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms (wherein —CH— in the alkyl group may be replaced with —O— or —CO—), still more preferably an iodine atom, a fluorine atom, a fluorinated alkyl group having 1 to 4 carbon atoms, a hydroxy group, a carboxy group, a hydroxyalkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, still more preferably an iodine atom, a fluorine atom, a perfluoroalkyl group having 1 to 3 carbon atoms, a hydroxy group, a carboxy group, a hydroxyalkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms, and still more preferably an iodine atom, a fluorine atom, a trifluoromethyl group, a hydroxy group, a carboxy group, a hydroxymethyl group, or a methoxy group.

[0184] Among them, R 3 As for m2, when m2 is 0, R 3 At least one of R is a fluorine atom or a fluorinated alkyl group having 1 to 6 carbon atoms. 3 At least one of is preferably a fluorine atom or a fluorinated alkyl group having 1 to 3 carbon atoms, more preferably a fluorine atom or a perfluoroalkyl group having 1 to 3 carbon atoms, even more preferably a fluorine atom or a trifluoromethyl group, and still more preferably a fluorine atom. 1 L 10 R bonded to the carbon atom adjacent to 3 is preferably an iodine atom, a fluorine atom, or a fluorinated alkyl group having 1 to 3 carbon atoms. 3At least one of is preferably an iodine atom, a fluorine atom, or a fluorinated alkyl group having 1 to 3 carbon atoms, more preferably an iodine atom, a fluorine atom, or a perfluoroalkyl group having 1 to 3 carbon atoms, further preferably an iodine atom, a fluorine atom, or a trifluoromethyl group, and still more preferably an iodine atom; m3 is 2, and two R 3 is an iodine atom or a combination of an iodine atom and a methoxy group.

[0185] R 6 is preferably a fluorine atom, a fluorinated alkyl group of 1 to 6 carbon atoms, or an alkyl group of 1 to 8 carbon atoms (wherein —CH2— contained in the alkyl group may be replaced with —O— or —CO—), more preferably a fluorine atom, a fluorinated alkyl group of 1 to 6 carbon atoms, or an alkyl group of 1 to 6 carbon atoms (wherein —CH2— contained in the alkyl group may be replaced with —O— or —CO—), even more preferably a fluorine atom, a fluorinated alkyl group of 1 to 4 carbon atoms, a hydroxy group, a carboxy group, a hydroxyalkyl group of 1 to 4 carbon atoms, or an alkoxy group of 1 to 4 carbon atoms, still more preferably a fluorine atom, a perfluoroalkyl group of 1 to 3 carbon atoms, a hydroxy group, a carboxy group, a hydroxyalkyl group of 1 to 4 carbon atoms, or an alkoxy group of 1 to 4 carbon atoms, and still more preferably a fluorine atom, a trifluoromethyl group, a hydroxy group, a carboxy group, a hydroxymethyl group, or a methoxy group.

[0186] Among them, R 6 is preferably a fluorine atom or a fluorinated alkyl group having 1 to 3 carbon atoms, more preferably a fluorine atom or a perfluoroalkyl group having 1 to 3 carbon atoms, even more preferably a fluorine atom or a trifluoromethyl group, and still more preferably a fluorine atom.

[0187] m3 is preferably an integer of 0 to 4, more preferably an integer of 1 to 4, even more preferably 1, 2 or 4, and even more preferably 1 or 2.

[0188] m6 is preferably an integer of 0 to 4, more preferably an integer of 1 to 4, and even more preferably 2, 3 or 4. m3+m6 is preferably an integer of 1 to 9, and more preferably an integer of 1 to 8.

[0189] R 3 Ar 1 The bonding position to Ar is not particularly limited. 1 is a group derived from a benzene ring, at least one R 3 But, L 2 It is preferable that the bond is made to the o-position or m-position relative to the bonding position of Ar 1 When is a group derived from a naphthalene ring, L 2 But, Ar 1 When the compound is bonded to the 1st or 2nd position of R, at least one R 3 But, Ar 1 It is preferred that the aryl group is bonded to the 3rd, 4th, 5th, 6th or 7th position of the aryl group.

[0190] R 6 Ar 2 The bonding position to Ar is not particularly limited. 2 is a group derived from a benzene ring, at least one R 6 But, L 3 It is preferable that the bond is made to the o-position or m-position relative to the bonding position of Ar 2 When is a group derived from a naphthalene ring, L 3 But, Ar 2 When the compound is bonded to the 1st or 2nd position of R, at least one R 6 But, Ar 2 It is preferred that the aryl group is bonded to the 3rd, 4th, 5th, 6th or 7th position of the aryl group.

[0191] Examples of the anion (I) include anions represented by the following formulae (Ia-1) to (Ia-142). Among these, anions represented by formulae (Ia-1) to (Ia-36), (Ia-45) to (Ia-54), and (Ia-109) to (Ia-142) are preferred.

[0192] [ka]

[0193] [ka]

[0194] [ka]

[0195] [ka]

[0196] [ka]

[0197] [ka]

[0198] [ka]

[0199] [ka]

[0200] [ka]

[0201] [ka]

[0202] [ka]

[0203] [ka]

[0204] [ka]

[0205] [ka]

[0206] [ka]

[0207] [ka]

[0208] [ka]

[0209] [ka]

[0210] [ka]

[0211] [Cation (I)] Z in formula (I) +Examples of the organic cation include organic onium cations, organic sulfonium cations, organic iodonium cations, organic ammonium cations, benzothiazolium cations, and organic phosphonium cations. Among these, organic sulfonium cations and organic iodonium cations are preferred, and arylsulfonium cations are more preferred. Specific examples include cations represented by any of formulas (b2-1) to (b2-5) (hereinafter, sometimes referred to as "cation (b2-1)" depending on the formula number).

[0212] [ka]

[0213] [In formulas (b2-1) to (b2-5), R b4 ~R b6 each independently represent a chain hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, or an aromatic hydrocarbon group having 6 to 36 carbon atoms, a hydrogen atom contained in the chain hydrocarbon group may be substituted with a hydroxy group, an alkoxy group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms, a hydrogen atom contained in the alicyclic hydrocarbon group may be substituted with a halogen atom, an aliphatic hydrocarbon group having 1 to 18 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, or a glycidyloxy group, and a hydrogen atom contained in the aromatic hydrocarbon group may be substituted with a halogen atom, a hydroxy group, an aliphatic hydrocarbon group having 1 to 18 carbon atoms, a fluorinated alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms.

[0214] R b4 and R b5 and may be bonded to each other to form a ring together with the sulfur atom to which they are attached, and -CH2- contained in the ring may be replaced with -O-, -S- or -CO-.

[0215] R b7 and R b8each independently represents a halogen atom, a hydroxy group, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, a fluorinated alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms.

[0216] m2 and n2 each independently represent an integer of 0 to 5; When m2 is 2 or more, multiple R b7 may be the same or different, and when n2 is 2 or more, multiple R b8 may be the same or different.

[0217] R b9 and R b10 each independently represents a chain hydrocarbon group having 1 to 36 carbon atoms or an alicyclic hydrocarbon group having 3 to 36 carbon atoms. R b9 and R b10 and may be bonded to each other to form a ring together with the sulfur atom to which they are attached, and -CH2- contained in the ring may be replaced with -O-, -S- or -CO-.

[0218] R b11 represents a hydrogen atom, a chain hydrocarbon group having 1 to 36 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms. R b12 represents a chain hydrocarbon group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms, and a hydrogen atom contained in the chain hydrocarbon group may be substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a hydrogen atom contained in the aromatic hydrocarbon group may be substituted with an alkoxy group having 1 to 12 carbon atoms or an alkylcarbonyloxy group having 1 to 12 carbon atoms.

[0219] R b11 and R b12 and may be bonded to each other to form a ring including the -CH-CO- to which they are bonded, and -CH2- contained in the ring may be replaced by -O-, -S- or -CO-.

[0220] R b13 ~R b18and R b21 ~R b26 each independently represents a halogen atom, a hydroxy group, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, a fluorinated alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms.

[0221] R b13 and R b14 and R b21 and R b22 may be bonded to each other to form a ring containing a sulfur atom together with the benzene ring to which they are attached, and -CH2- contained in the ring may be replaced by -O-, -S- or -CO-.

[0222] R b27 ~R b29 each independently represents a hydrogen atom or a group containing an acid labile group. L b31 and L b41 ~L b43 each independently represents a sulfur atom or an oxygen atom. o2, p2, s2, and t2 each independently represent an integer of 0 to 5.

[0223] q2 and r2 each independently represent an integer of 0 to 4; u2 represents 0 or 1. o21, p22, q23, r24, t25 and s26 each independently represent an integer of 0 to 4.

[0224] u3 represents an integer of 1 to 3, and satisfies 1≦u3+q23≦5. u4 and u5 each independently represent an integer of 0 to 3, and satisfy 0≦u4+o21≦5 and 0≦u5+p22≦5.

[0225] When o2 is 2 or more, multiple R b13 are the same or different, and when p2 is 2 or more, multiple R b14 are the same or different, and when q2 is 2 or more, multiple R b15 are the same or different, and when r2 is 2 or more, multiple R b16are the same or different, and when s2 is 2 or more, multiple R b17 are the same or different, and when t2 is 2 or more, multiple R b18 are the same or different.

[0226] When o21, p22, q23, r24, t25 and s26 are each 2 or more, multiple R b21 ~R b26 are the same or different. When u3, u4, and u5 each represent 2 or more, the groups in the parentheses are the same or different. When u2 is 0, any one of o2, p2, q2, and r2 is 1 or more, and R b13 ~R b16 At least one of o2, p2, s2, t2, q2, and r2 is preferably a halogen atom, and when u2 is 1, any one of o2, p2, s2, t2, q2, and r2 is 1 or more, and R b13 ~R b18 At least one of these is preferably a halogen atom.

[0227] Furthermore, when u2 is 0, r2 is preferably 1 or more, and more preferably 1. When u2 is 0 and r2 is 1 or more, R b16 is preferably a halogen atom.

[0228] The aliphatic hydrocarbon group refers to a chain hydrocarbon group and an alicyclic hydrocarbon group. Examples of the chain hydrocarbon group include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, octyl, and 2-ethylhexyl.

[0229] In particular, R b9 ~R b12 The chain hydrocarbon group preferably has 1 to 12 carbon atoms. The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and examples of the monocyclic alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and cyclodecyl. Examples of the polycyclic alicyclic hydrocarbon group include decahydronaphthyl, adamantyl, and norbornyl groups, as well as the following groups:

[0230] [ka]

[0231] In particular, R b9 ~R b12 The alicyclic hydrocarbon group preferably has 3 to 18 carbon atoms, and more preferably has 4 to 12 carbon atoms.

[0232] Examples of the alicyclic hydrocarbon group in which a hydrogen atom is substituted with an aliphatic hydrocarbon group include a methylcyclohexyl group, a dimethylcyclohexyl group, a 2-methyladamantan-2-yl group, a 2-ethyladamantan-2-yl group, a 2-isopropyladamantan-2-yl group, a methylnorbornyl group, an isobornyl group, etc. In the alicyclic hydrocarbon group in which a hydrogen atom is substituted with an aliphatic hydrocarbon group, the total number of carbon atoms in the alicyclic hydrocarbon group and the aliphatic hydrocarbon group is preferably 20 or less.

[0233] The fluorinated alkyl group refers to an alkyl group having 1 to 12 carbon atoms and a fluorine atom, and examples thereof include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a perfluorobutyl group, etc. The number of carbon atoms in the fluorinated alkyl group is preferably 1 to 9, more preferably 1 to 6, and even more preferably 1 to 4.

[0234] Examples of aromatic hydrocarbon groups include aryl groups such as a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, etc. The aromatic hydrocarbon group may have a chain hydrocarbon group or an alicyclic hydrocarbon group, and examples thereof include aromatic hydrocarbon groups having a chain hydrocarbon group (such as a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a p-ethylphenyl group, a p-tert-butylphenyl group, a 2,6-diethylphenyl group, and a 2-methyl-6-ethylphenyl group) and aromatic hydrocarbon groups having an alicyclic hydrocarbon group (such as a p-cyclohexylphenyl group and a p-adamantylphenyl group).

[0235] When the aromatic hydrocarbon group has a chain hydrocarbon group or an alicyclic hydrocarbon group, a chain hydrocarbon group having 1 to 18 carbon atoms and an alicyclic hydrocarbon group having 3 to 18 carbon atoms are preferred. Examples of aromatic hydrocarbon groups in which hydrogen atoms are substituted with alkoxy groups include p-methoxyphenyl groups.

[0236] Examples of the chain hydrocarbon group in which a hydrogen atom is substituted with an aromatic hydrocarbon group include aralkyl groups such as a benzyl group, a phenethyl group, a phenylpropyl group, a trityl group, a naphthylmethyl group, and a naphthylethyl group.

[0237] Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a decyloxy group, and a dodecyloxy group.

[0238] Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, and a butyryl group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0239] Examples of the alkylcarbonyloxy group include a methylcarbonyloxy group, an ethylcarbonyloxy group, a propylcarbonyloxy group, an isopropylcarbonyloxy group, a butylcarbonyloxy group, a sec-butylcarbonyloxy group, a tert-butylcarbonyloxy group, a pentylcarbonyloxy group, a hexylcarbonyloxy group, an octylcarbonyloxy group, and a 2-ethylhexylcarbonyloxy group.

[0240] R b4 and R b5 and bond to each other together with the sulfur atom to which they are bonded to form a ring which may be monocyclic, polycyclic, aromatic, non-aromatic, saturated, or unsaturated. This ring may be a ring having 3 to 18 carbon atoms, preferably a ring having 4 to 18 carbon atoms. The ring containing a sulfur atom may be a 3- to 12-membered ring, preferably a 3- to 7-membered ring, for example, the following rings. * represents a bonding site.

[0241] [ka]

[0242] R b9 and R b10 The ring formed by these together may be any of monocyclic, polycyclic, aromatic, non-aromatic, saturated and unsaturated rings. This ring may be a 3- to 12-membered ring, preferably a 3- to 7-membered ring. Examples thereof include a thiolan-1-ium ring (tetrahydrothiophenium ring), a thian-1-ium ring, and a 1,4-oxathian-4-ium ring.

[0243] R b11 and R b12 The ring formed by combining these may be any of monocyclic, polycyclic, aromatic, non-aromatic, saturated and unsaturated rings. Examples of this ring include a 3- to 12-membered ring, and preferably a 3- to 7-membered ring. Examples include an oxocycloheptane ring, an oxocyclohexane ring, an oxonorbornane ring, and an oxoadamantane ring.

[0244] R b27 ~R b29 Examples of groups containing an acid labile group include -R c30 , -CO-OR c30 or -L c10 -CO-OR c30 A group represented by (L c10 represents an alkanediyl group having 1 to 6 carbon atoms, and R c30 represents an acid labile group.

[0245] R b27 ~R b29 Examples of the acid labile group include group (1) and group (2) described below. Among the cations (b2-1) to (b2-5), the cation (b2-1), the cation (b2-4) or the cation (b2-5) is preferred.

[0246] Examples of the cation (b2-1) include the following cations.

[0247] [ka]

[0248] Examples of the cation (b2-2) include the following cations.

[0249] [ka]

[0250] Examples of the cation (b2-3) include the following cations.

[0251] [ka]

[0252] Examples of the cation (b2-4) include the following cations.

[0253] [ka]

[0254] Examples of the cation (b2-5) include the following cations.

[0255] [ka]

[0256] Specific examples of the salt (I) include salts formed by any combination of the above-mentioned cations and anions. Specific examples of the salt (I) are shown in the table below.

[0257] In the table below, each symbol represents the symbol attached to the structure representing the above-mentioned anion or cation, and "~" indicates that the salt (I) corresponds to the anion (I). For example, salt (I-1) is a salt consisting of an anion represented by formula (Ia-1) and a cation represented by formula (b2-c-1), salt (I-2) is a salt consisting of an anion represented by formula (Ia-2) and a cation represented by formula (b2-c-1), and salt (I-111) is a salt consisting of an anion represented by formula (Ia-1) and a cation represented by formula (b2-c-10).

[0258] For example, salt (I-1) is the salt shown below.

[0259] [ka]

[0260] [Table 1] JPEG2025174918000050.jpg230170 JPEG2025174918000051.jpg235170 JPEG2025174918000052.jpg199170

[0261] Among these, salt (I) is preferably a salt obtained by combining an anion represented by any one of formulas (Ia-1) to (Ia-36), (Ia-45) to (Ia-54), and (Ia-109) to (Ia-142) with a cation represented by any one of formulas (b2-c-1), (b2-c-10), (b2-c-13), (b2-c-14), (b2-c-18) to (b2-c-20), (b2-c-27), (b2-c-30), (b2-c-47), (b2-c-48), (b2-c-31), and (b2-c-50) to (b2-c-79).

[0262] <Method for producing salt (I)> Salt (I) can be produced, for example, by reacting a salt represented by formula (I-a1), a salt represented by formula (I-a2), or a salt represented by formula (I-a3) with a compound represented by formula (I-b1) in a solvent in the presence of a catalyst.

[0263] [ka]

[0264] (In the formula, the symbols other than those below have the same meanings as above. mm2 represents 0 or 1.) Furthermore, when m2 = 0, the salt (I0) can also be produced by reacting a salt represented by formula (I-a4) with a compound represented by formula (I-b2) or a compound represented by formula (I-b3) in a solvent in the presence of a catalyst. In the following formula, mm2A and mm2B each represent an integer of 0 to 5, and mm2A + mm2B = m4 is satisfied.

[0265] [ka]

[0266] Examples of the catalyst include potassium carbonate, potassium iodide, pyridine, diethylaminopyridine, triethylamine, sodium hydroxide, and carbonyldiimidazole.

[0267] Examples of the solvent include chloroform, monochlorobenzene, dimethylformamide, acetonitrile, ethyl acetate, and water. The reaction temperature is usually 5° C. to 100° C., and the reaction time is usually 0.5 to 24 hours.

[0268] Examples of salts represented by formula (I-a1) include the salts represented by the following formulas, which are readily available on the market and can also be easily produced by known production methods.

[0269] [ka]

[0270] Examples of salts represented by formula (I-a2) include the salts represented by the following formulas, which are readily available on the market and can also be easily produced by known production methods.

[0271] [ka]

[0272] Examples of salts represented by formula (I-a3) include the salts represented by the following formulas, which are readily available on the market and can also be easily produced by known production methods.

[0273] [ka]

[0274] [ka]

[0275] [ka]

[0276] Examples of salts represented by formula (I-a4) include the salts represented by the following formulas, which are readily available on the market and can also be easily produced by known production methods.

[0277] [ka]

[0278] Examples of compounds represented by formula (I-b1) include the compounds represented by the following formulas, which are readily available on the market and can also be easily produced by known production methods.

[0279] [ka]

[0280] [ka]

[0281] Examples of compounds represented by formula (I-b2) include the compounds represented by the following formulas, which are readily available on the market and can also be easily produced by known production methods.

[0282] [ka]

[0283] Examples of compounds represented by formula (I-b3) include the compounds represented by the following formulas, which are readily available on the market and can also be easily produced by known production methods.

[0284] [ka]

[0285] [Acid Generator] The acid generator of the present invention contains a salt (I). The acid generator may contain only one type of salt (I) or two or more types of salts (I).

[0286] The acid generator of the present invention may contain, in addition to the salt (I), a known acid generator that acts as an acid generator in the resist field (hereinafter, sometimes referred to as "acid generator (B)" or "compound (B)"). The acid generator (B) may be used alone or in combination of two or more.

[0287] When the acid generator contains a salt (I) and an acid generator (B), the ratio of the salt (I) to the acid generator (B) (mass ratio; salt (I):acid generator (B)) is usually 1:99 to 99:1, preferably 2:98 to 98:2, more preferably 5:95 to 95:5, even more preferably 10:90 to 90:10, and particularly preferably 15:85 to 85:15.

[0288] The acid generator (B) may be either a nonionic or ionic acid generator. Examples of nonionic acid generators include sulfonate esters (e.g., 2-nitrobenzyl esters, aromatic sulfonates, oximesulfonates, N-sulfonyloxyimides, sulfonyloxyketones, and diazonaphthoquinone 4-sulfonate), sulfones (e.g., disulfones, ketosulfones, and sulfonyldiazomethanes), and the like. Examples of ionic acid generators include onium salts containing onium cations (e.g., diazonium salts, phosphonium salts, sulfonium salts, and iodonium salts). Examples of anions of onium salts include sulfonate anions, sulfonylimide anions, sulfonylmethide anions, and carboxylate anions.

[0289] Furthermore, the acid generator (B) may be part of a structural unit that constitutes a resin contained in the resist composition, such as the structural unit (a7) described below. As the acid generator (B), compounds that generate an acid when exposed to radiation, such as those described in JP-A-63-26653, JP-A-55-164824, JP-A-62-69263, JP-A-63-146038, JP-A-63-163452, JP-A-62-153853, JP-A-63-146029, U.S. Pat. No. 3,779,778, U.S. Pat. No. 3,849,137, German Patent No. 3,914,407, and European Patent No. 126,712, can be used. Compounds produced by known methods may also be used.

[0290] Preferred examples of the acid generator (B) include a salt represented by formula (B1) (hereinafter sometimes referred to as "salt (B1)" or "acid generator (B1)") and a salt represented by formula (B2) (hereinafter sometimes referred to as "salt (B2)" or "acid generator (B2)"), excluding salt (I).

[0291] [ka]

[0292] [In formula (B1), L b1 represents a single bond or an (nb1+1)-valent hydrocarbon group which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-.

[0293] L b2 represents a single bond or a divalent hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-.

[0294] Y b1 represents an optionally substituted methyl group or an optionally substituted cyclic hydrocarbon group having 3 to 24 carbon atoms, and -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-.

[0295] nb1 represents an integer of 1 to 6. When nb1 is 2 or more, the groups in the parentheses may be the same or different. Z1 + represents an organic cation. L b1 The (nb1+1)-valent hydrocarbon group is a monovalent chain hydrocarbon group, a monovalent alicyclic hydrocarbon group, a monovalent aromatic hydrocarbon group, or a monovalent group that combines two or more of these groups, from which nb1 hydrogen atoms have been removed to form one or more L b2 The hydrocarbon group may have 1 to 48 carbon atoms, preferably 1 to 42, more preferably 1 to 36, even more preferably 1 to 30, still more preferably 1 to 24, and even more preferably 1 to 18.

[0296] Examples of the chain hydrocarbon group include groups in which nb1 hydrogen atoms have been removed from an alkyl group or an alkenyl group. The alkyl group may be linear or branched, and specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, undecanyl, dodecanyl, tridecanyl, tetradecanyl, pentane decanyl, and heptadecanyl. Examples of the alkenyl group include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl.

[0297] The number of carbon atoms in the chain hydrocarbon group can be 1 to 48, preferably 1 to 36, more preferably 1 to 24, even more preferably 1 to 20, still more preferably 1 to 18, even more preferably 1 to 12, and even more preferably 1 to 10.

[0298] Examples of the alicyclic hydrocarbon group include groups in which nb hydrogen atoms have been removed from a monocyclic or polycyclic cycloalkyl group. Examples of the monocyclic cycloalkyl group include a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0299] Examples of polycyclic cycloalkyl groups include cycloalkyl groups having a bridged structure, cycloalkyl groups in which two or more rings are fused, and cycloalkyl groups in which two rings are bonded via a spiro bond. Examples of cycloalkyl groups having a bridged structure include a norbornyl group and an adamantyl group. Examples of cycloalkyl groups in which two or more rings are fused include a bicyclo[4,4,0]decane group and a steroid group (steroid skeleton). Examples of cycloalkyl groups in which two rings are bonded via a spiro bond include spirocyclic cycloalkyl groups in which one cycloalkyl group selected from the group consisting of a cyclopentyl group, a cyclohexyl group, a norbornyl group, and an adamantyl group is bonded via a spiro bond to a cycloalkyl group having 5 to 8 carbon atoms. A double bond may be formed between two carbon atoms contained in the alicyclic hydrocarbon group.

[0300] More specifically, alicyclic hydrocarbon groups represented by the following formulas are included.

[0301] [ka]

[0302] When the alicyclic hydrocarbon group is a monocyclic cycloalkyl group, the number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 24, more preferably 3 to 20, even more preferably 3 to 18, still more preferably 3 to 12, even more preferably 3 to 10, and still more preferably 3 to 8. When the alicyclic hydrocarbon group is a polycyclic cycloalkyl group, the number of carbon atoms in the alicyclic hydrocarbon group is preferably 6 to 24, more preferably 6 to 20, even more preferably 6 to 18, still more preferably 6 to 12, and still more preferably 7 to 12.

[0303] Examples of aromatic hydrocarbon groups include groups in which nb1 hydrogen atoms have been removed from an aryl group. Examples of aryl groups include phenyl, naphthyl, anthryl, biphenyl, and fluorenyl groups. More specifically, examples of aromatic hydrocarbon groups include those represented by the following formulas:

[0304] [ka]

[0305] The number of carbon atoms in the aromatic hydrocarbon group is preferably 4 to 24, more preferably 4 to 20, even more preferably 4 to 18, still more preferably 5 to 14, even more preferably 5 to 10, and even more preferably 6 to 10.

[0306] L b1 When -CH2- in the hydrocarbon group is replaced with -O-, -CO-, -S- or -SO2-, the number of carbon atoms before replacement is regarded as the number of carbon atoms in the hydrocarbon group. L b1Among the hydrocarbon groups in the above, groups in which -CH2- in a chain hydrocarbon group is replaced by -O-, -CO-, -S- or -SO2- include a hydroxy group (a group in which -CH2- in a methyl group is replaced by -O-), a carboxy group (a group in which -CH2- in an ethyl group is replaced by -O-CO-), a carbonyl group (a group in which -CH2- in a methylene group is replaced by -CO-), an oxy group (a group in which -CH2- in a methylene group is replaced by -O-), an alkoxy group (a group in which -CH2- at any position in an alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which -CH2-CH2- at any position in an alkyl group is replaced by -O-CO-), an alkylcarbonyl group (an alkyl group Examples of such groups include alkyl, alkylcarbonyl, alkyloxy, alkyl groups in which -CH- at any position in the alkyl group is replaced with -CO-), alkylcarbonyloxy groups (in which -CH-CH- at any position in the alkyl group is replaced with -CO-O-), alkanediyloxy groups (in which -CH- at any position in the alkanediyl group is replaced with -O-), alkanediyloxycarbonyl groups (in which -CH-CH- at any position in the alkanediyl group is replaced with -O-CO-), alkanediylcarbonyl groups (in which -CH- at any position in the alkanediyl group is replaced with -CO-), and alkanediylcarbonyloxy groups (in which -CH-CH- at any position in the alkanediyl group is replaced with -CO-). These substituted groups include those exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms.

[0307] L b1 Among the hydrocarbon groups listed above, examples of groups in which -CH2- in an alicyclic hydrocarbon group is replaced with -O-, -CO-, -S-, or -SO2- include groups containing structures such as cyclic ether, cyclic ketone, cyclic ester (lactone), cyclic thioether, cyclic acetal, and cyclic sulfonate ester (sultone). Specific examples include alicyclic hydrocarbon groups represented by the following formula: The bonding position of the alicyclic hydrocarbon groups listed in the following formula may be any position.

[0308] [ka]

[0309] L b1 Among these hydrocarbon groups, -CH2- contained in the aromatic hydrocarbon group may be replaced by -O- or -S-, and examples of the group in which -CH2- is replaced by -O- or -S- include groups derived from a furan ring or a thiophene ring, respectively. Specific examples include aromatic hydrocarbon groups represented by the following formulas:

[0310] [ka]

[0311] Examples of the group combining two or more groups selected from the group consisting of a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group include a group combining the above-mentioned chain hydrocarbon group with the above-mentioned alicyclic hydrocarbon group, a group combining the above-mentioned chain hydrocarbon group with the above-mentioned aromatic hydrocarbon group, a group combining the above-mentioned alicyclic hydrocarbon group with the above-mentioned aromatic hydrocarbon group, and a group combining the above-mentioned chain hydrocarbon group with the above-mentioned alicyclic hydrocarbon group and the above-mentioned aromatic hydrocarbon group, and examples of the above-mentioned combined groups include the group combining the alicyclic hydrocarbon group with the aromatic hydrocarbon group, which may be a fused ring.

[0312] L b2 The divalent hydrocarbon group includes a divalent chain hydrocarbon group, a divalent alicyclic hydrocarbon group, a divalent aromatic hydrocarbon group, and a group combining two or more of these groups. A monovalent hydrocarbon group can be obtained by removing one hydrogen atom to form Y b1 Examples of such groups include groups that bond to the following:

[0313] L b2 The divalent chain hydrocarbon group, divalent alicyclic hydrocarbon group, divalent aromatic hydrocarbon group, and divalent group formed by combining two or more of these groups are each, within the range permitted by the upper limit of the number of carbon atoms, L b1Examples of the monovalent hydrocarbon group include a monovalent chain hydrocarbon group, a monovalent alicyclic hydrocarbon group, a monovalent aromatic hydrocarbon group, and a monovalent group obtained by combining two or more of these groups and removing one hydrogen atom from them.

[0314] L b1 and L b2 Examples of the substituent that the hydrocarbon group may have include a halogen atom, a cyano group, a nitro group, etc. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc.

[0315] L b1 and L b2 When L is a group in which an alicyclic hydrocarbon group or an aromatic hydrocarbon group is combined with a chain hydrocarbon group, the chain hydrocarbon group may be regarded as substantially a substituent that the alicyclic hydrocarbon group or the aromatic hydrocarbon group has. b1 and L b2 The -CH2- of the chain hydrocarbon group contained in the hydrocarbon group is replaced with -O-, -CO-, -S- or -SO2-, thereby forming L b1 and L b2 The hydrocarbon group may substantially have a substituent such as a hydroxy group, a carboxy group, a carbonyl group, an oxycarbonyl group, a carbonyloxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, a thiol group, an alkylthio group, or an alkylsulfonyl group.

[0316] Y b1 Examples of the cyclic hydrocarbon group include an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group in which an alicyclic hydrocarbon group and an aromatic hydrocarbon group are combined. Y b1 The alicyclic hydrocarbon group and the aromatic hydrocarbon group are represented by L b1 Examples of the alicyclic hydrocarbon groups and aromatic hydrocarbon groups include those similar to those exemplified in 1., and when they have no substituent, they may be monovalent alicyclic hydrocarbon groups and aromatic hydrocarbon groups.

[0317] Y b1Examples of the substituent that the methyl group in Y may have include a halogen atom, a cyano group, a hydroxy group, and a nitro group. b1 Examples of the substituent that the cyclic hydrocarbon group may have include a halogen atom, a cyano group, a nitro group, or a hydrocarbon group having 1 to 18 carbon atoms that may have a halogen atom, a cyano group, or a nitro group. -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO-, or -SO2-. Y b1 The number of carbon atoms in the hydrocarbon group that may be contained in the cyclic hydrocarbon group is b1 The carbon number of the cyclic hydrocarbon group is not included in the carbon number of the cyclic hydrocarbon group. The halogen atoms include L b1 and L b2 Examples of the halogen atoms include the same halogen atoms as those exemplified as the substituents of the above.

[0318] Y b1 Examples of the hydrocarbon group having 1 to 18 carbon atoms that may be substituted on the cyclic hydrocarbon group include chain hydrocarbon groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups combining these groups. Examples of the chain hydrocarbon group, alicyclic hydrocarbon group, aromatic hydrocarbon group, and groups combining two or more of these groups include, within the range permitted by the upper limit of the number of carbon atoms, L b1 Examples of the hydrocarbon groups include the chain hydrocarbon groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups in which two or more of these groups are combined, as exemplified by Y b1 Examples of the group in which -CH2- contained in the hydrocarbon group having 1 to 18 carbon atoms that the cyclic hydrocarbon group may have as a substituent is replaced with -O-, -S-, -CO- or -SO2- include the same groups as exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms. b1 The hydrocarbon group having 1 to 18 carbon atoms which may be substituted on the cyclic hydrocarbon group may constitute a protecting group or leaving group (acid labile group or base labile group) commonly used in the art.

[0319] The anion of the salt represented by formula (B1) is preferably an anion represented by the following formula (B1-A1) (hereinafter, sometimes referred to as "anion (B1-A1)") or an anion represented by formula (B1-A2) (hereinafter, sometimes referred to as "anion (B1-A2)").

[0320] [ka]

[0321] [In formula (B1-A1), L b2 and Y b1 has the same meaning as in formula (B1).

[0322] Q b1 , Q b2 , Q b3 and Q b4 each independently represents a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. z1 represents an integer of 0 to 6. When z1 is 2 or more, the groups in the parentheses may be the same or different.

[0323] X 1 represents -O-CO-, -CO-O-, -O-CO-O- or -O-. L b3 represents a single bond or an optionally substituted hydrocarbon group having 1 to 24 carbon atoms and a valence of (nb2+1), and one -CH2- in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-.

[0324] nb2 represents an integer of 1 to 3. When nb2 is 2 or greater, the groups in the parentheses may be the same or different.] Q b1 , Q b2 , Q b3 and Q b4Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group.

[0325] Q b1 , Q b2 , Q b3 and Q b4 Examples of the perfluoroalkyl group include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group, and a perfluorohexyl group.

[0326] Q b1 and Q b2 Q b1 and Q b2 At least one of the groups preferably contains a fluorine atom or a perfluoroalkyl group, more preferably a fluorine atom or a perfluoroalkyl group, even more preferably a fluorine atom or a trifluoromethyl group, and even more preferably both are fluorine atoms.

[0327] Q b3 and Q b4 are each preferably independently a hydrogen atom, a fluorine atom or a perfluoroalkyl group having 1 to 3 carbon atoms, and Q b3 is preferably a hydrogen atom, a fluorine atom, or a perfluoroalkyl group having 1 to 3 carbon atoms, and Q b4 is preferably a hydrogen atom or a fluorine atom.

[0328] z1 is preferably an integer of 0 to 3, and more preferably 0, 1 or 2. X 1 is preferably —O—CO— or —CO—O—.

[0329] L b3 As the hydrocarbon group in the formula (B1), within the range permitted by the upper limit of the number of carbon atoms, b1The same hydrocarbon groups as those exemplified above can be mentioned. L b3 is preferably a single bond, an optionally substituted chain hydrocarbon group of 1 to 12 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), an optionally substituted alicyclic hydrocarbon group of 3 to 18 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-), an optionally substituted aromatic hydrocarbon group of 6 to 10 carbon atoms (-CH2- contained in the aromatic hydrocarbon group may be replaced with -O- or -S-), or a group comprising a combination of two or more of these groups, and more preferably a single bond, an optionally substituted chain hydrocarbon group of 1 to 6 carbon atoms, or a group represented by the following formula (Lb3-1): When -CH2- in the chain hydrocarbon group is replaced with -O- or -CO-, the number of -CH2- in the chain hydrocarbon group replaced with -O- or -CO- is preferably 1 to 4, and it is preferred that one -CH2-CH2- in the chain hydrocarbon group is replaced with -O-CO- or -CO-O-, or one -CH2-CH2-CH2- in the chain hydrocarbon group is replaced with -O-CO-O-.

[0330] [ka]

[0331] [In formula (Lb3-1), nb2 has the same meaning as in formula (B1-A1).

[0332] L b31 represents a single bond or a chain hydrocarbon group having 1 to 12 carbon atoms, and -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-, and the chain hydrocarbon group may have a substituent.

[0333] W b3represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms, in which -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-, and -CH2- contained in the aromatic hydrocarbon group may be replaced with -O- or -S-, and the alicyclic hydrocarbon group and the aromatic hydrocarbon group may have a substituent.

[0334] * and ** represent binding sites, * represents X 1 represents the binding site with In formula (Lb3-1), L b31 The chain hydrocarbon group of L is as long as the upper limit of the carbon number allows. b1 Examples of the chain hydrocarbon groups include the same groups as those exemplified above.

[0335] In formula (Lb3-1), W b3 The alicyclic hydrocarbon group and aromatic hydrocarbon group of L are as long as the upper limit of the carbon number allows. b1 Examples of the alicyclic hydrocarbon groups and aromatic hydrocarbon groups are the same as those exemplified above.

[0336] In formula (Lb3-1), L b31 The substituents that the chain hydrocarbon group of W may have and b3 The substituents that the alicyclic hydrocarbon group and aromatic hydrocarbon group may have are b1 Examples of the substituent that the hydrocarbon group may have include the same groups as the substituents exemplified above.

[0337] L b31 is preferably a single bond or an alkanediyl group having 1 to 6 carbon atoms (-CH2- contained in the alkanediyl group may be replaced by -O- or -CO-).

[0338] Among them, W b3 The alicyclic hydrocarbon group and aromatic hydrocarbon group are preferably the alicyclic hydrocarbon group and aromatic hydrocarbon group shown below. In the alicyclic hydrocarbon group and aromatic hydrocarbon group shown below, * and ** represent a bonding site, * represents X 1 or L b31represents a bonding site with L, and ** represents a hydrogen atom, a substituent, or L b2 represents a binding site with L b2 represents a bonding site with. In the alicyclic hydrocarbon groups represented below, -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO-, or -SO2-. When -CH2- contained in the alicyclic hydrocarbon group is replaced with -O-, -S-, -CO-, or -SO2-, it is preferable that an ether ring, ester ring (lactone ring), carbonate ester ring, sulfonate ester ring (sultone ring), or acetal ring is formed.

[0339] [ka]

[0340] In formula (B1-A1), L b2 is preferably a single bond or a chain hydrocarbon group having 1 to 12 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), and is preferably a single bond, -O-, -O-CO-, -CO-O-, -O-CO-O- or -L b21 -X 2 -L b22 -**(L b21 and L b22 One of X represents a chain hydrocarbon group having at least 1 to 6 carbon atoms, and the other represents a single bond or a chain hydrocarbon group having 1 to 6 carbon atoms. 2 represents -O-, -CO-O-, -O-CO- or -O-CO-O-. * and ** represent bonding sites, and ** represents Y b1 represents the binding site with L b21 , X 2 and L b22 The total number of carbon atoms is 12 or less.

[0341] In formula (B1-A1), Y b1is preferably a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent (-CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -CO-, -S- or -SO2-), more preferably an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (-CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -CO-, -S- or -SO2-) or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and even more preferably an alicyclic hydrocarbon group having 3 to 16 carbon atoms which may have a substituent (-CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -CO-, -S- or -SO2-) or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. Specifically, groups represented by the following formulae (Y1) to (Y36) are more preferred. In formulae (Y1) to (Y36), R Yb is a hydrogen atom or Y b1 Among the substituents that the cyclic hydrocarbon group may have, R represents an alkyl group having 1 to 4 carbon atoms. Yc is a hydrogen atom or Y b1 represents a substituent that the cyclic hydrocarbon group of the formula (I) may have, and * represents a substituent that the cyclic hydrocarbon group of the formula (I) may have, b2 The alicyclic hydrocarbon group and aromatic hydrocarbon group represented by the following formulae may have other substituents, although not specifically shown in the following formulae.

[0342] [ka]

[0343] The anion represented by formula (B1-A1) is preferably an anion represented by formula (B1-A1-1) to formula (B1-A1-85) (hereinafter, sometimes referred to as "anion (B1-A1-1)" depending on the formula number), and more preferably an anion represented by any of formulas (B1-A1-1) to (B1-A1-4), (B1-A1-9), (B1-A1-10), (B1-A1-24) to (B1-A1-33), (B1-A1-36) to (B1-A1-40), and (B1-A1-47) to (B1-A1-85).

[0344] [ka]

[0345] [ka]

[0346] [ka]

[0347] where R i2 ~R i7 are each independently, for example, an alkyl group having 1 to 4 carbon atoms, preferably a methyl group or an ethyl group. i8 is, for example, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 5 to 12 carbon atoms, or a group formed by combining these, more preferably a methyl group, an ethyl group, a cyclohexyl group, or an adamantyl group. A41 is a single bond or an alkanediyl group having 1 to 4 carbon atoms.

[0348] Q b1 and Q b2 has the same meaning as above. Specific examples of the anion represented by formula (B1-A1) include the anions described in JP-A-2010-204646.

[0349] Preferred anions represented by formula (B1-A1) include those represented by formulas (B1a-1) to (B1a-70). Of these, anions represented by any of formulas (B1a-1) to (B1a-4), (B1a-7) to (B1a-11), (B1a-14) to (B1a-30), and (B1a-35) to (B1a-70) are preferred.

[0350] [ka]

[0351] [ka]

[0352] [ka]

[0353] The anion represented by formula (B1-A2) is represented by the following formula:

[0354] [ka]

[0355] [In formula (B1-A2), L b2 and Y b1 has the same meaning as in formula (B1).

[0356] R b1 represents a halogen atom or an alkyl group having 1 to 6 carbon atoms, and one --CH.sub.2-- contained in the alkyl group may be replaced with --O-- or --CO--. nb4 represents an integer of 1 to 5. When nb4 is 2 or greater, the groups in the parentheses may be the same or different.

[0357] nb3 represents an integer of 0 to 4. When nb3 is 2 or more, a plurality of R b1 may be the same or different from each other. However, 1≦nb4+nb3≦5 is satisfied. In formula (B1-A2), L b2 and Y b1 Examples of the cyclic hydrocarbon group include, within the upper limit of the carbon number, L in formula (B1). b2 and Y b1 Examples of the cyclic hydrocarbon group are the same as those of L. b2 hydrocarbon group, Y b1The substituents that the methyl group and the cyclic hydrocarbon group may have are also defined as follows: b2 hydrocarbon group, Y b1 Examples of the substituents that the methyl group and cyclic hydrocarbon group may have are the same as those listed above.

[0358] These hydrocarbon groups, methyl groups and cyclic hydrocarbon groups may have one or more substituents. L b2 is preferably a chain hydrocarbon group having 1 to 12 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), and more preferably -CO-OL b41 -(L b41 is a single bond or a chain hydrocarbon group having 1 to 6 carbon atoms, and -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-. * is SO3 - represents the bonding site with the benzene ring to which L is attached. b41 is preferably a single bond or a chain hydrocarbon group having 1 to 3 carbon atoms. ) and even more preferably *-CO-O-.

[0359] Y b1 is preferably a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent (-CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -CO-, -S- or -SO2-), more preferably an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (-CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -CO-, -S- or -SO2-), or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, and even more preferably Y in formula (B1-A1) b1 or L b1 Specifically, the groups represented by the above formulae (Y1) to (Y36) are preferred, and the groups represented by the above formulae (Y1) to (Y19) are more preferred.

[0360] Y b1The substituents that the cyclic hydrocarbon group may have are preferably a halogen atom or an alkyl group having 1 to 6 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O-, -S-, -CO- or -SO2-), more preferably a fluorine atom, an iodine atom or an alkyl group having 1 to 4 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O-, -S-, -CO- or -SO2-), still more preferably a fluorine atom, an iodine atom, a hydroxy group, an alkoxy group having 1 to 3 carbon atoms or an alkyl group having 1 to 4 carbon atoms, and still more preferably a fluorine atom, an iodine atom, a hydroxy group or an alkyl group having 1 to 4 carbon atoms. b2 The substituent that the cyclic hydrocarbon group may have may constitute a protecting group or leaving group (acid labile group or base labile group) that is commonly used in the art.

[0361] In formula (B1-A2), nb4 is preferably an integer of 1 to 4, more preferably an integer of 1 to 3, even more preferably 1 or 2, and even more preferably 2. When nb4 is 1 or 2, -L b2 -Y b1 The bond position of SO3 - Preferably, the following structure is substituted at the m-position of the benzene ring relative to the bonding position of the above.

[0362] [ka]

[0363] [In the above formula, L b2 , Y b1 , R b1 , nb3 has the same meaning as in formula (B1-A2). In formula (B1-A2), when nb4 is 2 or more, a plurality of L b2 and Y b1 are preferably the same group.

[0364] R b1Examples of the alkyl group having 1 to 6 carbon atoms include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, etc. The number of carbon atoms in the alkyl group is preferably 1 to 4, and more preferably 1 to 3.

[0365] R b1 Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of groups in which -CH- in an alkyl group is replaced with -O- or -CO- include a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an oxy group, a carbonyl group, etc. These substituted groups include the same groups as those exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms.

[0366] R b1 are each independently preferably a halogen atom or an alkyl group having 1 to 4 carbon atoms (wherein —CH2— contained in the alkyl group may be replaced with —O— or —CO—), more preferably a fluorine atom, an iodine atom or an alkyl group having 1 to 3 carbon atoms (wherein —CH2— contained in the alkyl group may be replaced with —O— or —CO—), and further preferably a fluorine atom, an iodine atom, a hydroxy group, a methoxy group or a methyl group.

[0367] nb3 is an integer of 0 to 4 (i.e., nb3-1 is an integer of 0 to 3), preferably an integer of 0 to 3, and more preferably an integer of 0 to 2. In one embodiment, nb3 is preferably 0. In another embodiment, nb3 is preferably 1 or 2. When nb3 is 1, R b1 is preferably a halogen atom, and R b1 is more preferably a fluorine atom or an iodine atom. When nb3 is 2, R b1 Preferably, one of R is a halogen atom and the other is a halogen atom or an alkyl group having 1 to 4 carbon atoms,b1 It is more preferable that one of the groups is a fluorine atom or an iodine atom, and the other is a fluorine atom, an iodine atom, or an alkyl group having 1 to 3 carbon atoms.

[0368] Examples of the anion represented by formula (B1-A2) include the following anions. Among them, the anions represented by formulas (B2a-1) to (B2a-20) are preferred, and the anions represented by formulas (B2a-1) to (B2a-11) and (B2a-16) to (B2a-20) are more preferred. The following anions are preferred in the case where some R b1 is omitted, and may contain substituents not shown.

[0369] [ka]

[0370] Examples of the acid generator (B2) include salts represented by the following formula:

[0371] [ka]

[0372] [In formula (B2), A 1 represents a nitrogen atom or a carbon atom.

[0373] L b2 ' represents a single bond or a divalent hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-.

[0374] Y b1 ' represents an optionally substituted methyl group or an optionally substituted cyclic hydrocarbon group having 3 to 24 carbon atoms, and -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-.

[0375] nb5 represents an integer of 2 or 3.1 When is a nitrogen atom, nb5 is 2, and A 1 When is a carbon atom, nb5 is 3. The groups in the parentheses may be the same or different from each other, and when two groups in the parentheses are bonded to form A 1 may form a ring containing:

[0376] Z2 + represents an organic cation. In formula (B2), L b2′ and Y b1′ Examples of the hydrocarbon group, cyclic hydrocarbon group and their substituents are L in formula (B1-A1). b2 and Y b1 The same groups as those shown below can be mentioned.

[0377] L b2 ′ is a single bond, *-L b23 -, *-L b23 -X 2 -or*-L b23 -X 2 -W 2 -X 3 -(L b23 represents a chain hydrocarbon group having 1 to 6 carbon atoms which may contain a fluorine atom. 2 and X 3 each independently represents -O-, -CO-O-, -O-CO-, -O-CO-O- or -O-. W 2 represents an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O- or -CO-. * represents a bonding site with SO2. ) is preferred.

[0378] Y b1is preferably a fluorine atom-containing methyl group or a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent (-CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -CO-, -S- or -SO2-), and more preferably a trifluoromethyl group, an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (-CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-), or an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. Specifically, it is preferably a trifluoromethyl group or a group represented by formulae (Y1) to (Y36) in formula (B1-A1).

[0379] In formula (B2), two -SO2-L b2 ′-Y b1 When the groups (B2′) are taken together to form a ring, an anion represented by the formula (B2′) can be given.

[0380] [ka]

[0381] [In formula (B2′), A 1 , Y b1‘ , L b2’ and nb5 have the same meaning as in formula (B2).

[0382] W b4 represents a disulfonylimide ring or disulfonylmide ring having 2 to 12 carbon atoms which may have a fluorine atom.] W b4 The disulfonylimide ring or disulfonylmide ring preferably has 3 to 12 carbon atoms, more preferably 3 to 6 carbon atoms, and the hydrogen atom of the methylene group contained in the ring is preferably substituted with a fluorine atom.

[0383] Examples of the anion in the salt represented by formula (B2) include the following: Among these, anions represented by formula (B3a-1), formula (B3a-2), formula (B3a-12) or formula (B3a-14) are preferred.

[0384] [ka]

[0385] In another embodiment of the acid generator (B), a salt in which the anion in the salt represented by formula (B1) is replaced with a carboxylate anion is also preferably used as the acid generator (B).

[0386] Examples of carboxylate anions include the following:

[0387] [ka]

[0388] Z1 + and Z2 + As the organic cation, Z in formula (I) + Examples of the organic cations include the same as those listed above.

[0389] The acid generator (B) is a combination of the above-mentioned anions and the above-mentioned organic cations, and these can be combined arbitrarily. Preferred examples of the acid generator (B) include combinations of anions represented by any of formulas (B1a-1) to (B1a-4), (B1a-7) to (B1a-11), (B1a-14) to (B1a-30), (B1a-35) to (B1a-70), (B2a-1) to (B2a-11), (B2a-16) to (B2a-20), (B3a-1) to (B3a-3), and (B3a-11) to (B3a-14) with cations (b2-1), (b2-2), (b2-3), (b2-4), and (b2-5).

[0390] Preferred examples of the acid generator (B) include those represented by formulae (B1-1) to (B1-105), (B2-1) to (B2-20), and (B3-1) to (B3-28). Among these, those containing an arylsulfonium cation are preferred, and those represented by formulae (B1-1) to (B1-3), (B1-5) to (B1-7), (B1-11) to (B1-14), (B1-20) to (B1-26), (B1-29), (B1-31) to (B1-105), (B2-1) to (B2-20), and (B3-1) to (B3-28) are particularly preferred.

[0391] [ka]

[0392] [ka]

[0393] [ka]

[0394] [ka]

[0395] [ka]

[0396] [ka]

[0397] [ka]

[0398] When the acid generator contains salt (I) and compound (B), the ratio of the salt (I) to compound (B) (mass ratio; salt (I): compound (B)) is usually 1:99 to 99:1, preferably 2:98 to 98:2, more preferably 5:95 to 95:5, even more preferably 10:90 to 90:10, and particularly preferably 15:85 to 85:15.

[0399] In the resist composition of the present invention, the content of salt (I) relative to the solid content of the resist composition is preferably 0.1 to 99.9% by mass, more preferably 1 to 45% by mass, even more preferably 1 to 40% by mass, and even more preferably 3 to 40% by mass. When the resist composition contains resin (A), described below, the content of salt (I) relative to 100 parts by mass of resin (A), described below, is preferably 1 to 45 parts by mass, more preferably 1 to 40 parts by mass, and even more preferably 3 to 40 parts by mass.

[0400] In the resist composition of the present invention, the content of compound (B) relative to the solid content of the resist composition is preferably 0.1 to 99.9% by mass, more preferably 1 to 45% by mass, even more preferably 1 to 40% by mass, and even more preferably 3 to 40% by mass. When the resist composition contains resin (A), described below, the content of compound (B) relative to 100 parts by mass of resin (A), described below, is preferably 1 to 45 parts by mass, more preferably 1 to 40 parts by mass, and even more preferably 3 to 40 parts by mass.

[0401] In the resist composition of the present invention, the total content of the acid generators is preferably 0.1 to 99.9% by mass, more preferably 1 to 45% by mass, even more preferably 1 to 40% by mass, and even more preferably 3 to 40% by mass, relative to the solid content of the resist composition. When the resist composition contains a resin (A) described below, the total content of the acid generators is preferably 1 to 45 parts by mass, more preferably 1 to 40 parts by mass, and even more preferably 3 to 40 parts by mass, relative to 100 parts by mass of the resin (A) described below.

[0402] <Resist composition> The resist composition of the present invention contains an acid generator containing a salt (I). The resist composition of the present invention may further contain a resin. Examples of the resin include a resin containing a structural unit having an acid labile group (hereinafter sometimes referred to as "resin (A)") and / or a resin other than resin (A). Here, the term "acid labile group" refers to a group that has a leaving group and that is eliminated upon contact with an acid, converting the structural unit into a structural unit having a hydrophilic group (e.g., a hydroxy group or a carboxy group).

[0403] The resist composition of the present invention preferably contains a quencher such as a salt that generates an acid with a weaker acidity than the acid generated from the acid generator (hereinafter may be referred to as "quencher (C)"), and preferably contains a solvent (hereinafter may be referred to as "solvent (E)").

[0404] <Resin (A)> Resin (A) contains a structural unit having an acid labile group (hereinafter sometimes referred to as "structural unit (a1)"). Resin (A) preferably further contains a structural unit other than structural unit (a1). Examples of structural units other than structural unit (a1) include a structural unit not having an acid labile group (hereinafter sometimes referred to as "structural unit (s)") and structural units derived from other monomers known in the art.

[0405] <Structural unit (a1)> The structural unit (a1) is derived from a monomer having an acid labile group (hereinafter sometimes referred to as "monomer (a1)").

[0406] The acid labile group contained in the resin (A) is preferably a group represented by formula (1) (hereinafter also referred to as group (1)) and / or a group represented by formula (2) (hereinafter also referred to as group (2)).

[0407] [ka]

[0408] [In formula (1), R a1 , R a2 and R a3 each independently represents 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 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining any of these; or R a1 and R a2 are bonded to each other to form, together with the carbon atoms to which they are bonded, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, and the alkyl group, the alkenyl group, the alicyclic hydrocarbon group and the aromatic hydrocarbon group may have a halogen atom.

[0409] ma and na each independently represent 0 or 1, and at least one of ma and na represents 1. * denotes a binding site.]

[0410] [ka]

[0411] [In formula (2), R a1′ and R a2′ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; R a3′ represents a hydrocarbon group having 1 to 20 carbon atoms, or R a2′ and R a3′are bonded to each other to form, together with the carbon atom to which they are bonded and X, a heterocyclic group having 3 to 20 carbon atoms, and -CH2- contained in the hydrocarbon group and the heterocyclic group may be replaced with -O- or -S-, and the hydrocarbon group and the heterocyclic group may have a halogen atom.

[0412] X represents an oxygen atom or a sulfur atom. na' represents 0 or 1. * denotes a binding site.] R a1 , R a2 and R a3 Examples of the alkyl group in include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.

[0413] R a1 , R a2 and R a3 Examples of the alkenyl group in the formula (I) include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups.

[0414] R a1 , R a2 and R a3 The alicyclic hydrocarbon group in may be either monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of polycyclic alicyclic hydrocarbon groups include decahydronaphthyl, adamantyl, and norbornyl groups, as well as the following groups (* indicates a bonding site): a1 , R a2 and R a3 The alicyclic hydrocarbon group preferably has 3 to 16 carbon atoms.

[0415] [ka]

[0416] R a1 , R a2 and R a3 Examples of the aromatic hydrocarbon group include aryl groups such as a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, and a phenanthryl group.

[0417] Examples of the combined group include a group in which the above-mentioned alkyl group and alicyclic hydrocarbon group are combined (for example, an alkylcycloalkyl group or cycloalkylalkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, a methylnorbornyl group, a cyclohexylmethyl group, an adamantylmethyl group, an adamantyldimethyl group, or a norbornylethyl group), an aralkyl group such as a benzyl group, an aromatic hydrocarbon group having an alkyl group (a p-methylphenyl group, a p-tert-butylphenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a 2,6-diethylphenyl group, a 2-methyl-6-ethylphenyl group, or the like), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (a p-cyclohexylphenyl group, a p-adamantylphenyl group, or the like), and an aryl-cycloalkyl group such as a phenylcyclohexyl group.

[0418] Preferably, ma is 0 and na is 1. R a1 and R a2 -C(R a1 )(R a2 )(R a3 ) includes the following groups. The alicyclic hydrocarbon group preferably has 3 to 12 carbon atoms. * represents the bonding site with -O-.

[0419] [ka]

[0420] R a1′ , R a2′ and R a3′ Examples of the hydrocarbon group in include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these groups.

[0421] Alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups combining these groups are R a1 , R a2 and R a3 Examples of the groups include the same as those listed in the above. R a2′ and R a3′ When they are bonded to each other to form a heterocyclic group together with the carbon atoms to which they are bonded and X, -C(R a1′ )(R a2′ )-XR a3′ Examples of the groups include the following: * represents a binding site.

[0422] [ka]

[0423] R a1′ and R a2′ At least one of these is preferably a hydrogen atom. na' is preferably 0.

[0424] R a1 , R a2 , R a3 , R a1′ , R a2′ and R a3′ The halogen atom that may be contained in the ring may be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. Examples of the group (1) include the following groups.

[0425] In formula (1), R a1 , R a2 and R a3 is an alkyl group, ma=0, and na=1. The group is preferably a tert-butoxycarbonyl group. In formula (1), R a1 , R a2 together with the carbon atom to which they are attached form an adamantyl group, and R a3 is an alkyl group, ma=0, and na=1.

[0426] In formula (1), R a1 and R a2 are each independently an alkyl group, and R a3 is an adamantyl group, ma=0, and na=1. Specific examples of the group (1) include the following: * represents a binding site.

[0427] [ka]

[0428] Specific examples of group (2) include the following groups: * represents a binding site.

[0429] [ka]

[0430] The monomer (a1) is preferably a monomer having an acid labile group and an ethylenically unsaturated bond, more preferably a (meth)acrylic monomer having an acid labile group.

[0431] Of the (meth)acrylic monomers having an acid labile group, preferred are those having an alicyclic hydrocarbon group having 5 to 20 carbon atoms. When a resin (A) having a structural unit derived from a monomer (a1) having a bulky structure such as an alicyclic hydrocarbon group is used in a resist composition, the resolution of the resist pattern can be improved.

[0432] Examples of structural units derived from a (meth)acrylic monomer having group (1) include a structural unit represented by formula (a1-0) (hereinafter sometimes referred to as structural unit (a1-0)), a structural unit represented by formula (a1-1) (hereinafter sometimes referred to as structural unit (a1-1)), or a structural unit represented by formula (a1-2) (hereinafter sometimes referred to as structural unit (a1-2)). Preferably, at least one structural unit selected from the group consisting of structural unit (a1-0), structural unit (a1-1), and structural unit (a1-2) is used, and more preferably at least one or two structural units selected from the group consisting of structural unit (a1-1) and structural unit (a1-2). These may be used alone or in combination of two or more.

[0433] [ka]

[0434] [In formula (a1-0), formula (a1-1), and formula (a1-2), all symbols have the same meanings as defined above.] R a01 , R a4 , R a5 The halogen atom in the formula (I) may be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

[0435] R a01 , R a4 , R a5Examples of the alkyl group optionally having a halogen atom in the formula (I) include a trifluoromethyl group, a difluoromethyl group, a methyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, an ethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a propyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a butyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a pentyl group, a hexyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, and an iodomethyl group. The number of carbon atoms in the alkyl group is preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 or 2. The alkyl group is preferably a methyl group or an ethyl group, and more preferably a methyl group.

[0436] R a01 , R a4 and R a5 is preferably a hydrogen atom or a methyl group, more preferably a methyl group. L a01 , L a1 and L a2 is preferably an oxygen atom or —O—(CH2) k01 It is —CO—O— (wherein k01 is preferably an integer of any one of 1 to 4, more preferably 1), and more preferably an oxygen atom.

[0437] R a02 , R a03 , R a04 , R a6 and R a7 The alkyl group, alkenyl group, alicyclic hydrocarbon group, aromatic hydrocarbon group and combinations thereof in the formula (1) include R a1 , R a2 and R a3 Examples of the groups include the same groups as those listed in the above.

[0438] R a02 , R a03 , and R a04The alkyl group in the formula (I) is preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group or an ethyl group, and even more preferably a methyl group.

[0439] R a6 and R a7 The alkyl group in the formula (I) is preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group, an ethyl group, an isopropyl group, or a t-butyl group, and even more preferably an ethyl group, an isopropyl group, or a t-butyl group.

[0440] R a6 and R a7 The alkenyl group in the formula (I) is preferably an alkenyl group having 2 to 6 carbon atoms, and more preferably an ethenyl group, a propenyl group, an isopropenyl group, or a butenyl group.

[0441] R a02 , R a03 , R a04 , R a6 and R a7 The alicyclic hydrocarbon group preferably has 5 to 12 carbon atoms, and more preferably 5 to 10 carbon atoms. R a02 , R a03 , R a04 , R a6 and R a7 The aromatic hydrocarbon group preferably has 6 to 12 carbon atoms, and more preferably 6 to 10 carbon atoms.

[0442] In the group in which an alkyl group and an alicyclic hydrocarbon group are combined, the total number of carbon atoms in the combination of the alkyl group and the alicyclic hydrocarbon group is preferably 18 or less. In the group in which an alkyl group and an aromatic hydrocarbon group are combined, the total number of carbon atoms in the combination of the alkyl group and the aromatic hydrocarbon group is preferably 18 or less.

[0443] R a02 and R a03is preferably an alkyl group having 1 to 6 carbon atoms which may have a halogen atom or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a halogen atom, and more preferably a methyl group, ethyl group, phenyl group or naphthyl group which may have a halogen atom.

[0444] R a04 is preferably an alkyl group having 1 to 6 carbon atoms which may have a halogen atom or an alicyclic hydrocarbon group having 5 to 12 carbon atoms which may have a halogen atom, and more preferably a methyl group, ethyl group, cyclohexyl group or adamantyl group which may have a halogen atom.

[0445] R a6 and R a7 is preferably an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, an alkenyl group having 2 to 6 carbon atoms which may have a halogen atom, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a halogen atom, more preferably a methyl group, ethyl group, isopropyl group, t-butyl group, ethenyl group, phenyl group, or naphthyl group which may have a halogen atom, and even more preferably an ethyl group, isopropyl group, t-butyl group, ethenyl group, or phenyl group which may have a halogen atom.

[0446] m1 is preferably an integer of 0 to 3, and more preferably 0 or 1. n1 is preferably an integer of 0 to 3, and more preferably 0 or 1. n1' is preferably 0 or 1.

[0447] Examples of the structural unit (a1-0) include structural units represented by any one of formulas (a1-0-1) to (a1-0-24) and R a01and structural units in which the methyl group corresponding to the formula (a1-0-1) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group (an alkyl group having a halogen atom) or another alkyl group, and structural units represented by any of formulas (a1-0-1) to (a1-0-10), (a1-0-13), (a1-0-14), and (a1-0-19) to (a1-0-24) are preferred.

[0448] [ka]

[0449] Examples of the structural unit (a1-1) include structural units derived from monomers described in JP-A-2010-204646. Among these, structural units represented by any one of formulas (a1-1-1) to (a1-1-7) and R in the structural unit (a1-1) are preferred. a4 A structural unit in which the methyl group corresponding to the formula (a1-1-1) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group is preferred, and a structural unit represented by any one of formulas (a1-1-1) to (a1-1-4) is more preferred.

[0450] [ka]

[0451] The structural unit (a1-2) includes a structural unit represented by any one of formulas (a1-2-1) to (a1-2-20) and R a5 and structural units in which the methyl group corresponding to the formula (a1-2-2), (a1-2-5), (a1-2-6), and (a1-2-10) to (a1-2-20) are substituted with a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group.

[0452] [ka]

[0453] When the resin (A) contains the structural unit (a1-0) and / or the structural unit (a1-1) and / or the structural unit (a1-2), the total content of these structural units, based on the total structural units of the resin (A), can be 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, even more preferably 25 mol% or more, even more preferably 30 mol% or more, even more preferably 40 mol% or more, and even more preferably 50 mol% or more. Also, the total content can be 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, the total content can be 10 to 95 mol%, preferably 15 to 90 mol%, more preferably 20 to 85 mol%, even more preferably 25 to 70 mol%, and even more preferably 30 to 70 mol%.

[0454] When the resin (A) contains the structural unit (a1-0), the content thereof, based on the total structural units of the resin (A), can be 5 mol% or more, preferably 10 mol% or more, more preferably 15 mol% or more, even more preferably 20 mol% or more, still more preferably 25 mol% or more, even more preferably 30 mol% or more, and still more preferably 35 mol% or more. It can also be 80 mol% or less, preferably 75 mol% or less, more preferably 70 mol% or less, even more preferably 65 mol% or less, and still more preferably 60 mol% or less. Specifically, it can be 5 to 80 mol%, preferably 5 to 75 mol%, more preferably 10 to 70 mol%, even more preferably 10 to 65 mol%, and still more preferably 10 to 60 mol%.

[0455] When the resin (A) contains the structural unit (a1-1) and / or the structural unit (a1-2), the total content of these units relative to the total structural units of the resin (A) can be 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, even more preferably 25 mol% or more, still more preferably 30 mol% or more, even more preferably 40 mol% or more, and still more preferably 50 mol% or more. Also, the total content can be 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 80 mol% or less, still more preferably 75 mol% or less, even more preferably 70 mol% or less, and still more preferably 65 mol% or less. Specifically, it can be 10 to 90 mol%, preferably 15 to 85 mol%, more preferably 15 to 80 mol%, even more preferably 20 to 80 mol%, still more preferably 20 to 75 mol%, even more preferably 20 to 70 mol%, even more preferably 20 to 60 mol%, and still more preferably 20 to 55 mol%.

[0456] An example of the structural unit (a1) having the group (2) is a structural unit represented by formula (a1-4) (hereinafter, sometimes referred to as "structural unit (a1-4)").

[0457] [ka]

[0458] [In formula (a1-4), all symbols have the same meanings as defined above.] R a1 and R a17 Examples of the halogen atom in the formula include a fluorine atom, a chlorine atom, and a bromine atom.

[0459] R a1Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in the formula (I) include a trifluoromethyl group, a difluoromethyl group, a methyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, an ethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a propyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a butyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a pentyl group, a hexyl group, and a perfluorohexyl group.

[0460] R a1 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group. R a17 Examples of the alkyl group in include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, even more preferably a methyl group or an ethyl group, and even more preferably a methyl group.

[0461] R a17 Examples of the haloalkyl group include a trifluoromethyl group, a difluoromethyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, etc. The number of carbon atoms in the haloalkyl group is preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 to 2.

[0462] R a17Examples of the alkoxy group in include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, and a hexyloxy group. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably an alkoxy group having 1 to 3 carbon atoms, even more preferably a methoxy group or an ethoxy group, and even more preferably a methoxy group.

[0463] R a17 Examples of the alkoxyalkyl group in the formula (I) include a methoxymethyl group, an ethoxyethyl group, a propoxymethyl group, an isopropoxymethyl group, a butoxymethyl group, a sec-butoxymethyl group, and a tert-butoxymethyl group. The alkoxyalkyl group is preferably an alkoxyalkyl group having 2 to 8 carbon atoms, more preferably an alkoxyalkyl group having 2 to 4 carbon atoms, even more preferably a methoxymethyl group or an ethoxyethyl group, and even more preferably a methoxymethyl group.

[0464] R a17 Examples of the alkoxyalkoxy group in include a methoxymethoxy group, a methoxyethoxy group, an ethoxymethoxy group, an ethoxyethoxy group, a propoxymethoxy group, an isopropoxymethoxy group, a butoxymethoxy group, a sec-butoxymethoxy group, and a tert-butoxymethoxy group. The alkoxyalkoxy group is preferably an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably an alkoxyalkoxy group having 2 to 4 carbon atoms, and even more preferably a methoxyethoxy group or an ethoxyethoxy group.

[0465] R a17 Examples of the alkylcarbonyl group in the formula (I) include an acetyl group, a propionyl group, a butyryl group, etc. The alkylcarbonyl group is preferably an alkylcarbonyl group having 2 to 4 carbon atoms, more preferably an alkylcarbonyl group having 2 to 3 carbon atoms, and even more preferably an acetyl group.

[0466] R a17Examples of the alkylcarbonyloxy group in the formula (I) include an acetyloxy group, a propionyloxy group, and a butyryloxy group. The alkylcarbonyloxy group is preferably an alkylcarbonyloxy group having 2 to 4 carbon atoms, more preferably an alkylcarbonyloxy group having 2 to 3 carbon atoms, and even more preferably an acetyloxy group.

[0467] R a17 is preferably a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 4 carbon atoms which may have a halogen atom, an alkoxy group having 1 to 4 carbon atoms or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group or an ethoxymethoxy group, and even more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group or an ethoxyethoxy group.

[0468] A a11 Examples of the alkanediyl group include straight-chain alkyl groups such as methylene, ethylene, propane-1,3-diyl, propane-1,2-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl, nonane-1,9-diyl, decane-1,10-diyl, undecane-1,11-diyl, and dodecane-1,12-diyl. and branched alkanediyl groups such as butane-1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, 2-methylbutane-1,4-diyl, heptane-1,6-diyl, octane-1,7-diyl, nonane-1,8-diyl, decane-1,9-diyl, and undecane-1,10-diyl. The number of carbon atoms in the alkanediyl group is preferably 1 to 10, more preferably 1 to 8, even more preferably 1 to 6, still more preferably 1 to 4, still more preferably 1 to 3, and even more preferably 1 or 2.

[0469] R a18Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, and a tert-butyl group. A a11 -CH2- in the alkanediyl group is -O-, -CO- or -NR a18 When substituted with -, the number of carbon atoms before substitution is regarded as the number of carbon atoms of the alkanediyl group.

[0470] A a11 -CH2- in the alkanediyl group is -O-, -CO- or -NR a18 The groups substituted with - include a hydroxy group (a group in which -CH2- in a methyl group is replaced with -O-), a carboxy group (a group in which -CH2-CH2- in an ethyl group is replaced with -O-CO-), a carbonyl group (a group in which -CH2- in a methylene group is replaced with -CO-), an oxy group (a group in which -CH2- in a methylene group is replaced with -O-), an amino group (a group in which -CH2- in an alkanediyl group is replaced with -NR a28 -), alkoxy group (a group in which -CH2- at any position in an alkyl group is replaced with -O-), alkoxycarbonyl group (a group in which -CH2-CH2- at any position in an alkyl group is replaced with -O-CO-), alkylcarbonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -CO-), alkylamino group (a group in which -CH2- in an alkyl group is replaced with -NR a18 -), peptide group (the -CH2-CH2- contained in the ethylene group is replaced by -CO-NR a18-), alkanediyloxy group (a group in which -CH2- at any position contained in an alkanediyl group is replaced with -O-), alkanediyloxycarbonyl group (a group in which -CH2-CH2- at any position contained in an alkanediyl group is replaced with -O-CO-), alkanediylcarbonyl group (a group in which -CH2- at any position contained in an alkanediyl group is replaced with -CO-), alkanediylcarbonyloxy group (a group in which -CH2-CH2- at any position contained in an alkanediyl group is replaced with -CO-O-), an alkanediylsulfonyl group (a group in which -CH2- at any position contained in an alkanediyl group is replaced with -SO2-), an alkanediylthio group (a group in which -CH2- at any position contained in an alkanediyl group is replaced with -S-), an alkanediylamino group (a group in which -CH2- at any position contained in an alkanediyl group is replaced with -NR a18 These substituted groups include the same as those exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms.

[0471] For example, A a11 -CH2- in the alkanediyl group is -O-, -CO- or -NR a18 Groups substituted with - include *-O-, *-CO-O-, *-O-CO-, and *-CO-OA. a12 -CO-O-, *-O-CO-A a12 -O-, *-OA a12 -CO-O-, *-CO-OA a12 -O-CO-, *-O-CO-A a12 -O-CO-, *-CO-NR a18 Among them, *-CO-O- and *-CO-OA a12 -CO-O-, *-OA a12 -CO-O-, *-CO-NR a18 - is preferred, where A a12 represents an alkanediyl group having 1 to 8 carbon atoms, and * represents R a1 A represents the bonding site with the carbon atom to which it is attached. a12 The alkanediyl group of A is, within the limits of the upper limit of the carbon number, a11Examples of the alkanediyl groups include the same alkanediyl groups as those shown in the above.

[0472] A a11 is a single bond, *-CO-O- or *-CO-OA a12 -CO-O- is preferred, a single bond, *-CO-O- or *-CO-O-CH2-CO-O- is more preferred, and a single bond or *-CO-O- is even more preferred.

[0473] na1 is preferably 1, 2, 3 or 4, more preferably 1, 2 or 3, and even more preferably 1 or 2. na11 is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, and even more preferably 0 or 1.

[0474] mc is preferably 0 or 1. R a34 , R a35 and R a36 Examples of the hydrocarbon group in include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group in which these groups are combined.

[0475] Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Examples of polycyclic alicyclic hydrocarbon groups include decahydronaphthyl, adamantyl, and norbornyl groups, as well as the following groups (* indicates a bonding site):

[0476] [ka]

[0477] Examples of the aromatic hydrocarbon group include aryl groups such as a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, and a phenanthryl group.

[0478] Examples of the combined group include a group in which the above-mentioned alkyl group and alicyclic hydrocarbon group are combined (for example, an alkylcycloalkyl group or cycloalkylalkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, a methylnorbornyl group, a cyclohexylmethyl group, an adamantylmethyl group, an adamantyldimethyl group, or a norbornylethyl group), an aralkyl group such as a benzyl group, an aromatic hydrocarbon group having an alkyl group (a p-methylphenyl group, a p-tert-butylphenyl group, a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a 2,6-diethylphenyl group, a 2-methyl-6-ethylphenyl group, or the like), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (a p-cyclohexylphenyl group, a p-adamantylphenyl group, or the like), and an aryl-cycloalkyl group such as a phenylcyclohexyl group. In particular, R a36 Examples of the group include an alkyl group having 1 to 18 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 formed by combining these.

[0479] R a35 and R a36 Examples of the divalent cyclic hydrocarbon group having 2 to 20 carbon atoms that are formed by bonding together with the -CO- to which they are bonded include the following groups: * represents a bonding site, and one of the groups is R a34 This is the binding site for

[0480] [ka]

[0481] R a34 is preferably a hydrogen atom. R a35 is preferably a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and more preferably a methyl group or an ethyl group.

[0482] R a36The hydrocarbon group in R is preferably an alkyl group having 1 to 18 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 formed by combining these, and more preferably an alkyl group having 1 to 18 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, or an aralkyl group having 7 to 18 carbon atoms. a36 The alkyl group and alicyclic hydrocarbon group in R are preferably unsubstituted. a36 The aromatic hydrocarbon group in is preferably an aromatic ring having an aryloxy group having 6 to 10 carbon atoms.

[0483] -OC(R a34 )(R a35 )-OR a36 and -CO-OC(R a34 )(R a35 )-OR a36 is eliminated upon contact with an acid (e.g., p-toluenesulfonic acid) to form a hydroxy group or a carboxy group.

[0484] -X a1 -OC(R a34 )(R a35 )-OR a36 In the case of a benzene ring, A a11 It is preferable that at least one of them is bonded to the o-position or the m-position, and more preferable that it is bonded to the p-position. In the case of a naphthalene ring, A a11 When the bonding position of A is the 1st position, it may be bonded to any of the 2nd to 8th positions. a11 When the bonding position of A is the 2nd position, it may be bonded to any of the 1st position and the 3rd to 8th positions. a11 When the bonding position of A is position 1, at least one of A is preferably bonded to position 3 to 6, and more preferably bonded to position 3 or 4. a11 When the bonding position is the 2nd position, it is preferably bonded to the 4th to 7th positions, and more preferably bonded to the 5th or 6th position.

[0485] Examples of the structural unit (a1-4) include structural units derived from monomers described in JP-A-2010-204646. Preferred are structural units represented by formulas (a1-4-1) to (a1-4-42) and R in the structural unit (a1-4). a1 and more preferably, the structural units represented by formulae (a1-4-1) to (a1-4-5), (a1-4-10), (a1-4-13), (a1-4-14), (a1-4-19), and (a1-4-20).

[0486] [ka]

[0487] [ka]

[0488] When the resin (A) contains the structural unit (a1-4), the content thereof, based on the total of all structural units in the resin (A), can be 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, even more preferably 25 mol% or more, even more preferably 30 mol% or more, even more preferably 40 mol% or more, and even more preferably 50 mol% or more. It can also be 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 80 mol% or less, even more preferably 75 mol% or less, even more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, it is preferably 10 to 95 mol%, more preferably 15 to 90 mol%, even more preferably 20 to 85 mol%, even more preferably 20 to 70 mol%, and particularly preferably 20 to 60 mol%.

[0489] Examples of the structural unit derived from a (meth)acrylic monomer having the group (2) include a structural unit represented by formula (a1-5) (hereinafter, sometimes referred to as "structural unit (a1-5)").

[0490] [ka]

[0491] [In formula (a1-5), all symbols have the same meanings as defined above.] R a8 Examples of the halogen atom in include a fluorine atom, an iodine atom, a chlorine atom and a bromine atom, with a fluorine atom being preferred.

[0492] R a8 Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in the formula (I) include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, and a perfluorohexyl group.

[0493] In formula (a1-5), R a8 is preferably a hydrogen atom, a methyl group or a trifluoromethyl group. L 51 is preferably an oxygen atom.

[0494] L 52 and L 53 Among these, it is preferred that one is —O— and the other is —S—. s1 is preferably 1. s1' is preferably an integer of 0 to 2.

[0495] Za1 is preferably a single bond or —CH2—CO—O—. Examples of the structural unit (a1-5) include structural units derived from monomers described in JP-A-2010-61117. Among these, the structural units represented by formulas (a1-5-1) to (a1-5-4) are preferred, and the structural unit represented by formula (a1-5-1) or (a1-5-2) is more preferred.

[0496] [ka]

[0497] When the resin (A) contains the structural unit (a1-5), the content thereof, based on the total structural units of the resin (A), can be 1 mol% or more, preferably 2 mol% or more, more preferably 3 mol% or more, even more preferably 5 mol% or more, even more preferably 10 mol% or more, even more preferably 20 mol% or more, and even more preferably 25 mol% or more. Also, the content can be 80 mol% or less, preferably 70 mol% or less, more preferably 60 mol% or less, even more preferably 50 mol% or less, even more preferably 45 mol% or less, even more preferably 40 mol% or less, and even more preferably 30 mol% or less. Specifically, the content is preferably 1 to 50 mol%, more preferably 3 to 45 mol%, even more preferably 5 to 40 mol%, and even more preferably 5 to 30 mol%.

[0498] An example of the structural unit (a1) having the group (1) is a structural unit represented by formula (a1-6) (hereinafter, sometimes referred to as "structural unit (a1-6)").

[0499] [ka]

[0500] [In formula (a1-6), all symbols have the same meanings as defined above.] R a61Examples of the halogen atom in include a fluorine atom, a bromine atom, an iodine atom and a chlorine atom, with a fluorine atom being preferred.

[0501] R a61 Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in the formula (I) include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, and a perfluorohexyl group.

[0502] R a61 is preferably a hydrogen atom, a methyl group or a trifluoromethyl group. R a62 , R a63 and R a64 Examples of the alkyl group in include a methyl group, an ethyl group, a propyl group, a butyl group, a heptyl group, a hexyl group, etc. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, and even more preferably a methyl group or an ethyl group.

[0503] R a62 , R a63 and R a64 The cyclic hydrocarbon group in the formula (I) includes an alicyclic hydrocarbon group and an aromatic hydrocarbon group. The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. Examples of polycyclic alicyclic hydrocarbon groups include a decahydronaphthyl group, an adamantyl group, and a norbornyl group. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 16, and more preferably 3 to 12.

[0504] Examples of the aromatic hydrocarbon group include a phenylene group and a naphthylene group. Examples of the substituent that the cyclic hydrocarbon group may have include 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.

[0505] R a62 and R a63 Examples of the ring formed by bonding together include an adamantane ring, a cyclopentane ring, and a cyclohexane ring. a62 and R a63 -C(R a62 )(R a63 )(R a64 ) includes the following groups. * represents the bonding site with the oxygen atom. The number of carbon atoms in the ring is preferably 3 to 16, and more preferably 3 to 12.

[0506] [ka]

[0507] L a61 and L a62 Examples of the alkanediyl group having 1 to 4 carbon atoms in the formula include a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a butane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, and a 2-methylpropane-1,2-diyl group.

[0508] L a61 and L a62 are each preferably independently a methylene group or an ethylene group. X a61 is preferably a single bond or —CO—O—*, and more preferably a single bond.

[0509] X a62 is preferably a single bond or *-OL a61 -, and more preferably a single bond. Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms for Ar include a phenylene group, an o-methylphenylene group, an m-methylphenylene group, a p-methylphenylene group, a p-ethylphenylene group, a p-tert-butylphenylene group, a 1-naphthylene group, a 2-naphthylene group, a 1-anthrylene group, a 9-anthrylene group, a biphenylene group, a 1-phenanthrylene group, and a 2-phenanthrylene group.

[0510] Examples of the substituent that the aromatic hydrocarbon group may have include 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.

[0511] Examples of the halogen atom include a fluorine atom, an iodine atom, a chlorine atom, and a bromine atom. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group, and even more preferably a methyl group.

[0512] Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, and a hexyloxy group. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably a methoxy group or an ethoxy group, and even more preferably a methoxy group.

[0513] Examples of the alkoxyalkyl group include a methoxymethyl group, an ethoxyethyl group, a propoxymethyl group, an isopropoxymethyl group, a butoxymethyl group, a sec-butoxymethyl group, and a tert-butoxymethyl group. The alkoxyalkyl group is preferably an alkoxyalkyl group having 2 to 8 carbon atoms, more preferably a methoxymethyl group or an ethoxyethyl group, and even more preferably a methoxymethyl group.

[0514] Examples of the alkoxyalkoxy group include a methoxymethoxy group, a methoxyethoxy group, an ethoxymethoxy group, an ethoxyethoxy group, a propoxymethoxy group, an isopropoxymethoxy group, a butoxymethoxy group, a sec-butoxymethoxy group, and a tert-butoxymethoxy group. The alkoxyalkoxy group is preferably an alkoxyalkoxy group having 2 to 8 carbon atoms, and more preferably a methoxyethoxy group or an ethoxyethoxy group.

[0515] Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, and a butyryl group. The alkylcarbonyl group is preferably an alkylcarbonyl group having 2 to 3 carbon atoms, and more preferably an acetyl group.

[0516] Examples of the alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, and a butyryloxy group. The alkylcarbonyloxy group is preferably an alkylcarbonyloxy group having 2 to 3 carbon atoms, and more preferably an acetyloxy group.

[0517] The substituent is preferably a halogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group, or an ethoxymethoxy group, and even more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, or an ethoxyethoxy group.

[0518] Ar is preferably a phenylene group which may have a substituent, and more preferably a phenylene group which may have a hydroxy group. Examples of the structural unit (a1-6) include structural units represented by formulas (a1-6-1) to (a1-6-44), preferably structural units represented by formulas (a1-6-1) to (a1-6-9), and (a1-6-39) to (a1-6-44), more preferably structural units represented by formulas (a1-6-1), (a1-6-2), (a1-6-4), (a1-6-5), (a1-6-7), (a1-6-8), and (a1-6-39) to (a1-6-44), and even more preferably structural units represented by formulas (a1-6-7), (a1-6-8), and (a1-6-39) to (a1-6-44). In the structural units represented by formulas (a1-6-1) to (a1-6-44), R a61 The structural unit (a1-6) includes a structural unit in which a methyl group corresponding to the following is replaced with a hydrogen atom or the like, and a structural unit in which a hydrogen atom is replaced with a methyl group or the like.

[0519] [ka]

[0520] When the resin (A) contains the structural unit (a1-6), the content thereof, based on the total structural units of the resin (A), can be 3 mol% or more, preferably 5 mol% or more, more preferably 7 mol% or more, even more preferably 10 mol% or more, still more preferably 20 mol% or more, even more preferably 30 mol% or more, and even more preferably 40 mol% or more. Also, the content can be 80 mol% or less, preferably 75 mol% or less, more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, the content is preferably 3 to 80 mol%, more preferably 5 to 75 mol%, even more preferably 7 to 70 mol%, even more preferably 7 to 65 mol%, and particularly preferably 10 to 60 mol%.

[0521] Further, examples of the structural unit (a1) include the following structural units.

[0522] [ka]

[0523] When the resin (A) or the like contains structural units represented by formulas (a1-7-1) to (a1-7-7), the content of these structural units relative to the total structural units of the resin (A) or the like is preferably 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, even more preferably 25 mol% or more, even more preferably 30 mol% or more, even more preferably 40 mol% or more, and even more preferably 50 mol% or more. The content may also be 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 80 mol% or less, even more preferably 75 mol% or less, even more preferably 70 mol% or less, and even more preferably 60 mol% or less. Specifically, the content is preferably 10 to 95 mol%, more preferably 15 to 90 mol%, even more preferably 20 to 85 mol%, even more preferably 20 to 70 mol%, and particularly preferably 20 to 60 mol%.

[0524] Further, examples of the structural unit (a1) include the following structural units.

[0525] [ka]

[0526] When the resin (A) or the like contains structural units represented by formulas (a1-8-1) to (a1-8-3), the content of these structural units relative to the total structural units of the resin (A) or the like is typically 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, even more preferably 25 mol% or more, even more preferably 30 mol% or more, even more preferably 40 mol% or more, and even more preferably 50 mol% or more. The content may also be 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, even more preferably 80 mol% or less, even more preferably 75 mol% or less, even more preferably 70 mol% or less, and even more preferably 60 mol% or less. Specifically, the content is preferably 10 to 60 mol%, more preferably 15 to 55 mol%, even more preferably 20 to 50 mol%, even more preferably 20 to 45 mol%, and particularly preferably 20 to 40 mol%.

[0527] <Structural unit(s)> The structural unit (s) is derived from a monomer (hereinafter sometimes referred to as "monomer (s)") that does not have an acid labile group. As the monomer from which the structural unit (s) is derived, a monomer that does not have an acid labile group known in the resist field can be used.

[0528] The structural unit (s) preferably has a hydroxy group, a carboxy group, or a lactone ring. The resist composition of the present invention may contain a resin containing a structural unit having a hydroxy group or a carboxy group but no acid labile group (hereinafter sometimes referred to as "structural unit (a2)") and / or a structural unit having a lactone ring but no acid labile group (hereinafter sometimes referred to as "structural unit (a3)"), thereby improving the resolution of the resist pattern and adhesion to the substrate. In addition to the structural units described above, structural units (s) may also include structural units having a halogen atom (hereinafter sometimes referred to as "structural unit (a4)"), structural units having a non-leaving hydrocarbon group (hereinafter sometimes referred to as "structural unit (a5)"), structural units having a sultone structure (hereinafter sometimes referred to as "structural unit (a6)"), structural units that decompose upon exposure to generate acid (hereinafter sometimes referred to as "structural unit (a7)"), and other structural units known in the art.

[0529] <Structural unit (a2)> The structural unit (a2) is a structural unit represented by formula (a2) and has an alcoholic hydroxy group, a phenolic hydroxy group, or a carboxy group.

[0530] [ka]

[0531] [In formula (a2), R a2 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom.

[0532] A a21 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and -CH2- contained in the alkanediyl group is -O-, -CO- or -NR a28 - may be replaced with

[0533] R a28 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. La21 represents a single bond or a hydrocarbon group having 1 to 28 carbon atoms, the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced with -O-, -CO-, -S- or -SO2-.

[0534] L a22 represents a single bond or a chain hydrocarbon group of 1 to 12 carbon atoms which may have a fluorine atom, and -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-.

[0535] na2 represents an integer of 1 to 5. When na2 is 2 or more, a plurality of L a22 may be the same or different from each other. R a2 Examples of the halogen atom in the formula include a fluorine atom, an iodine atom, a chlorine atom, and a bromine atom.

[0536] R a2 Examples of the alkyl group having 1 to 6 carbon atoms, which may have a halogen atom, include a trifluoromethyl group, a difluoromethyl group, a methyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, an ethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a propyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a butyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a pentyl group, a hexyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, and an iodomethyl group. The number of carbon atoms in the alkyl group is preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 or 2.

[0537] R a2 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group. A a21Examples of the alkanediyl group include straight-chain alkyl groups such as methylene, ethylene, propane-1,3-diyl, propane-1,2-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl, nonane-1,9-diyl, decane-1,10-diyl, undecane-1,11-diyl, and dodecane-1,12-diyl. and branched alkanediyl groups such as butane-1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, 2-methylbutane-1,4-diyl, heptane-1,6-diyl, octane-1,7-diyl, nonane-1,8-diyl, decane-1,9-diyl, and undecane-1,10-diyl. The number of carbon atoms in the alkanediyl group is preferably 1 to 10, more preferably 1 to 8, even more preferably 1 to 6, still more preferably 1 to 4, still more preferably 1 to 3, and even more preferably 1 or 2.

[0538] R a28 Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. A a21 -CH2- in the alkanediyl group is -O-, -CO- or -NR a28 When substituted with -, the number of carbon atoms before substitution is regarded as the number of carbon atoms of the alkanediyl group.

[0539] A a21 -CH2- in the alkanediyl group is -O-, -CO- or -NR a28As described above, examples of the group substituted for - include a hydroxy group, a carboxy group, a carbonyl group, an oxy group, an amino group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylamino group, a peptide group, an alkanediyloxy group, an alkanediyloxycarbonyl group, an alkanediylcarbonyl group, an alkanediylcarbonyloxy group, an alkanediylsulfonyl group, an alkanediylthio group, an alkanediylamino group, etc. These substituted groups include the same groups as those exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms.

[0540] A a21 -CH2- in the alkanediyl group is -O-, -CO- or -NR a28 Groups substituted with - include *-O-, *-CO-O-, *-O-CO-, and *-CO-OA. a22 -CO-O-, *-O-CO-A a22 -O-, *-OA a22 -CO-O-, *-CO-OA a22 -O-CO-, *-O-CO-A a22 -O-CO-, *-CO-NR a28 Among them, *-CO-O- and *-CO-OA a22 -CO-O-, *-OA a22 -CO-O-, *-CO-NR a28 - is preferred, where A a22 represents an alkanediyl group having 1 to 8 carbon atoms, and * represents R a2 A represents the bonding site with the carbon atom to which it is attached. a22 The alkanediyl group of A is, within the limits of the upper limit of the carbon number, a21 Examples of the alkanediyl groups include the same alkanediyl groups as those shown in the above.

[0541] A a21 is a single bond, *-CO-O- or *-CO-OA a22 -CO-O- is preferred, a single bond, *-CO-O- or *-CO-O-CH2-CO-O- is more preferred, and a single bond or *-CO-O- is even more preferred.

[0542] La21 The hydrocarbon group in is a (na2+1)-valent hydrocarbon group, and examples thereof include linear or branched chain hydrocarbon groups, monocyclic or polycyclic (including spiro rings, fused rings, or bridged rings) alicyclic hydrocarbon groups, and cyclic hydrocarbon groups such as aromatic hydrocarbon groups, and may also be a group combining two or more of these groups (for example, a hydrocarbon group formed from an alicyclic hydrocarbon group or an aromatic hydrocarbon group and a chain hydrocarbon group).

[0543] L a21 Examples of the chain hydrocarbon group include divalent to hexavalent chain hydrocarbon groups such as an alkanediyl group, an alkanetriyl group, an alkanetetrayl group, an alkanpentyl group, and an alkanehexyl group.

[0544] Examples of the alkanediyl group include A a21 Examples of the alkanediyl groups include the same alkanediyl groups as those shown in the above. Examples of the alkanetriyl group include a methanetriyl group, an ethanetriyl group, a propanetriyl group, a butanetriyl group, a pentanetriyl group, a hexanetriyl group, a heptanetriyl group, an octanetriyl group, a nonanetriyl group, a decantriyl group, an undecanetriyl group, a dodecanetriyl group, a tridecanetriyl group, a tetradecanetriyl group, a pentadecanetriyl group, a hexadecanetriyl group, and a heptadecanetriyl group.

[0545] Examples of the alkanetetrayl group include a methanetetrayl group, an ethanetetrayl group, a propanetetrayl group, a butanetetrayl group, a pentanetetrayl group, a hexanetetrayl group, a heptanetetrayl group, an octanetetrayl group, a nonanetetrayl group, a decanetetrayl group, an undecanetetrayl group, a dodecanetetrayl group, a tridecanetetrayl group, a tetradecanetetrayl group, a pentadecanetetrayl group, a hexadecanetetrayl group, and a heptadecanetetrayl group.

[0546] Further examples include groups in which one or more hydrogen atoms of the above groups are replaced with bonding sites. The number of carbon atoms in the chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 12, even more preferably 1 to 10, still more preferably 1 to 9, even more preferably 1 to 8, still more preferably 1 to 6, even more preferably 1 to 5, and particularly preferably 1 to 4.

[0547] L a21 Examples of the monocyclic and polycyclic alicyclic hydrocarbon groups in the above formula include the following alicyclic hydrocarbon groups: The binding site can be at any position.

[0548] [ka]

[0549] Examples include divalent to hexavalent alicyclic hydrocarbon groups such as a cycloalkanediyl group, a cycloalkanetriyl group, a cycloalkanetetrayl group, a cycloalkanepentyl group, and a cycloalkanehexyl group.

[0550] Specifically, monocyclic alicyclic hydrocarbon groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclooctane-1,5-diyl group, cyclopropanetriyl group, cyclobutanetriyl group, cyclopentanetriyl group, cyclohexanetriyl group, cycloheptanetriyl group, cyclooctanetriyl group, cyclodecanetriyl group, cyclopropanetetrayl group, cyclobutanetetrayl group, cyclopentanetetrayl group, cyclohexanetetrayl group, cycloheptanetetrayl group, cyclooctanetetrayl group, and cyclodecanetetrayl group; Examples of polycyclic alicyclic hydrocarbon groups include norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, decahydronaphthalenediyl group, bicyclo[3.3.0]octanediyl group, norbornanetriyl group, adamantanetriyl group, decahydronaphthalenetriyl group, bicyclo[3.3.0]octanetriyl group, norbornanetetrayl group, adamantanetetrayl group, decahydronaphthalenetetrayl group, and bicyclo[3.3.0]octanetetrayl group.

[0551] Further examples include groups in which one or more hydrogen atoms of the above groups are replaced with bonding sites. The alicyclic hydrocarbon group preferably has 3 to 20 carbon atoms, more preferably 3 to 18 carbon atoms, even more preferably 3 to 16 carbon atoms, even more preferably 3 to 12 carbon atoms, still more preferably 6 to 12 carbon atoms, and particularly preferably 6 to 10 carbon atoms.

[0552] L a21 Examples of the aromatic hydrocarbon group in include divalent to hexavalent aromatic hydrocarbon groups such as an arylene group, an arenetriyl group, an arenetetrayl group, an arenetyl group, and an arenehexyl group.

[0553] Specific examples include a phenylene group, a naphthylene group, an anthrylene group, a biphenylene group, a phenanthrylene group, a benzenetriyl group, a naphthalenetriyl group, an anthracenetriyl group, a biphenylenetriyl group, a phenanthrenetriyl group, a benzenetetrayl group, a naphthalenetetrayl group, an anthracenetetrayl group, a biphenylenetetrayl group, and a phenanthrenetetrayl group.

[0554] Further examples include groups in which one or more hydrogen atoms of the above groups have been replaced with bonding sites. The aromatic hydrocarbon group preferably has 6 to 20 carbon atoms, more preferably 6 to 18, even more preferably 6 to 14, still more preferably 6 to 12, and even more preferably 6 to 10.

[0555] Examples of the group combining two or more types include a group combining an alicyclic hydrocarbon group with a chain hydrocarbon group, a group combining an aromatic hydrocarbon group with a chain hydrocarbon group, a group combining an alicyclic hydrocarbon group with an aromatic hydrocarbon group, and a group combining an alicyclic hydrocarbon group with a chain hydrocarbon group and an aromatic hydrocarbon group. In the combination, two or more types of each of the alicyclic hydrocarbon group, aromatic hydrocarbon group, and chain hydrocarbon group may be combined. In addition, when any group is A a21 and L a22 may be bound to

[0556] Examples of groups in which -CH2- in a hydrocarbon group is replaced by -O-, -S-, -SO2- or -CO- include a hydroxy group (a group in which -CH2- in a methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- in an ethyl group is replaced by -O-CO-), a thiol group (a group in which -CH2- in a methyl group is replaced by -S-), an alkoxy group (a group in which -CH2- at any position in an alkyl group is replaced by -O-), and an alkylthio group (a group in which -CH2- at any position in an alkyl group is replaced by -S-). a group in which -CH2-CH2- at any position in an alkyl group is replaced with -O-CO-), an alkoxycarbonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -SO2-), an alkylcarbonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -CO-), an alkylcarbonyloxy group (a group in which -CH2-CH2- at any position in an alkyl group is replaced with -CO-O-), an oxy group (a group in which -CH2- in a methylene group is replaced with -O-), an alkylsulfonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -SO2-), an alkylcarbonyloxy group (a group in which -CH2- a carbonyl group (a group in which -CH2- in a methylene group is replaced with -CO-), a thio group (a group in which -CH2- in a methylene group is replaced with -S-), a sulfonyl group (a group in which -CH2- in a methylene group is replaced with -SO2-), an alkanediyloxy group (a group in which -CH2- at any position in an alkanediyl group is replaced with -O-), an alkanediyloxycarbonyl group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -O-CO-), an alkanediylcarbonyl group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -O-CO-), an alkanediyloxycarbonyl group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -O-CO-), an alkanediylcarbonyl group (a group in which an alkanediyl group in which -CH2- at any position is replaced with -CO-), an alkanediylcarbonyloxy group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -CO-O-), an alkanediylsulfonyl group (a group in which -CH2- at any position in an alkanediyl group is replaced with -SO2-), an alkanediylthio group (a group in which -CH2- at any position in an alkanediyl group is replaced with -S-), a cycloalkoxy group, a cycloalkylalkoxy group, an alkoxycarbonyloxy group,Examples of such groups include an aromatic hydrocarbon group-carbonyloxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy group, and a group that combines two or more of these groups. Also included are groups in which one or more hydrogen atoms of these groups have been replaced with a bonding site.

[0557] Examples of the alkoxy group include alkoxy groups having 1 to 27 carbon atoms, such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, etc. The number of carbon atoms in the alkoxy group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3.

[0558] Examples of the alkylthio group include alkylthio groups having 1 to 27 carbon atoms, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, etc. The number of carbon atoms in the alkylthio group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3.

[0559] Examples of the alkoxycarbonyl group include alkoxycarbonyl groups having 2 to 27 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, and butoxycarbonyl. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 28 carbon atoms, such as acetyl, propionyl, and butyryl. Examples of the alkylcarbonyloxy group include alkylcarbonyloxy groups having 2 to 27 carbon atoms, such as acetyloxy, propionyloxy, and butyryloxy. The number of carbon atoms in the alkoxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and even more preferably 2 or 3. The alkylcarbonyloxy group preferably has 2 to 11 carbon atoms, more preferably 2 to 6 carbon atoms, even more preferably 2 to 4 carbon atoms, and even more preferably 2 or 3 carbon atoms.

[0560] Examples of the alkylsulfonyl group include alkylsulfonyl groups having 1 to 27 carbon atoms, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, etc. The number of carbon atoms in the alkylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3.

[0561] Examples of the alkanediyloxy group include alkanediyloxy groups having 1 to 27 carbon atoms, such as a methyleneoxy group, an ethyleneoxy group, a propanediyloxy group, a butanediyloxy group, a pentanediyloxy group, etc. The number of carbon atoms in the alkanediyloxy group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3.

[0562] Examples of the alkanediyloxycarbonyl group include alkanediyloxycarbonyl groups having 2 to 27 carbon atoms, such as a methyleneoxycarbonyl group, an ethyleneoxycarbonyl group, a propanediyloxycarbonyl group, and a butanediyloxycarbonyl group. Examples of the alkanediylcarbonyl group include alkanediylcarbonyl groups having 2 to 28 carbon atoms, such as a methylenecarbonyl group, an ethylenecarbonyl group, a propanediylcarbonyl group, a butanediylcarbonyl group, and a pentanediylcarbonyl group. Examples of the alkanediylcarbonyloxy group include alkanediylcarbonyloxy groups having 2 to 27 carbon atoms, such as a methylenecarbonyloxy group, an ethylenecarbonyloxy group, a propanediylcarbonyloxy group, and a butanediylcarbonyloxy group. The number of carbon atoms in the alkanediyloxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. The number of carbon atoms in the alkanediylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. The number of carbon atoms in the alkanediylcarbonyloxy group is preferably 2 to 11, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3.

[0563] Examples of the alkanediylthio group include alkanediylthio groups having 1 to 27 carbon atoms, such as a methylenethio group, an ethylenethio group, a propanediylthio group, etc. The number of carbon atoms in the alkanediylthio group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3.

[0564] Examples of the alkanediylsulfonyl group include alkanediylsulfonyl groups having 1 to 27 carbon atoms, such as a methylenesulfonyl group, an ethylenesulfonyl group, a propylenesulfonyl group, etc. The number of carbon atoms in the alkanediylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3.

[0565] Examples of cycloalkoxy groups include cycloalkoxy groups having 3 to 27 carbon atoms, such as a cyclohexyloxy group. Examples of cycloalkylalkoxy groups include cycloalkylalkoxy groups having 4 to 27 carbon atoms, such as a cyclohexylmethoxy group. Examples of alkoxycarbonyloxy groups include alkoxycarbonyloxy groups having 2 to 26 carbon atoms, such as a butoxycarbonyloxy group. Examples of aromatic hydrocarbon group-carbonyloxy groups include aromatic hydrocarbon group-carbonyloxy groups having 7 to 27 carbon atoms, such as a benzoyloxy group. Examples of aromatic hydrocarbon group-carbonyl groups include aromatic hydrocarbon group-carbonyl groups having 7 to 28 carbon atoms, such as a benzoyl group. Examples of aromatic hydrocarbon group-oxy groups include aromatic hydrocarbon group-oxy groups having 6 to 27 carbon atoms, such as a phenyloxy group.

[0566] Examples of groups in which -CH2- in an alicyclic hydrocarbon group is replaced with -O-, -S-, -CO-, or -SO2- include the following groups. Further examples include groups in which -O- is replaced with -S- and -CO- is replaced with -SO2- among the groups shown below. The bonding site can be at any position.

[0567] [ka]

[0568] Examples of the combined group in which -CH2- is replaced by -O-, -S-, -CO- or -SO2- include the following groups: The bonding site can be at any position.

[0569] [ka]

[0570] L a21 The hydrocarbon group in may have one or more substituents, such as a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, an alkyl group having 1 to 16 carbon atoms (wherein —CH2— contained in the alkyl group may be replaced by —O— or —CO—), an acryloyloxy group, or a methacryloyloxy group.

[0571] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. L a21 The hydrocarbon group in the formula (I) may have a halogen atom as a substituent, thereby substantially having a substituent such as a haloalkyl group. Examples of the haloalkyl group include alkyl fluoride, alkyl chloride, alkyl bromide, and alkyl iodide, such as a chloromethyl group, bromomethyl group, iodomethyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, and perfluorobutyl group. The number of carbon atoms in the haloalkyl group is preferably 1 to 8, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3.

[0572] L a21 The hydrocarbon group of L a21can substantially have a substituent such as an alkyl group. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, a 2-ethylhexyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, and a dodecyl group. The number of carbon atoms in the alkyl group is preferably 1 to 12, more preferably 1 to 10, even more preferably 1 to 8, still more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3.

[0573] L a21 L is a group in which -CH2- in the hydrocarbon group is replaced by -O-, -S-, -CO- or -SO2-. a21 can substantially have a substituent such as a hydroxy group, a carboxy group, a thiol group, an alkylthio group, an alkylsulfonyl group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkoxyalkyl group, an alkoxyalkoxy group, an acryloyloxy group, or a methacryloyloxy group.

[0574] L a21 The substituents that the hydrocarbon group in the formula (I) may have are preferably a halogen atom, a haloalkyl group having 1 to 8 carbon atoms, or an alkyl group having 1 to 12 carbon atoms (wherein —CH— contained in the alkyl group may be replaced with —O— or —CO—), more preferably a halogen atom, a haloalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 10 carbon atoms (wherein —CH— contained in the alkyl group may be replaced with —O— or —CO—), still more preferably a halogen atom, a haloalkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, or an alkoxyalkoxy group having 2 to 8 carbon atoms, still more preferably a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, a hydroxy group, a methoxy group, an ethoxy group, an ethoxyethoxy group, or an ethoxymethoxy group, still more preferably a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, a hydroxy group, a methoxy group, or an ethoxyethoxy group.

[0575] Also, L a21 When the alkanediyl group is replaced by -O- or -CO-, etc., for example, *-L a23 -X a21 -(L a23 represents an alkanediyl group having 1 to 8 carbon atoms, and X a21 represents -O-, -O-CO-, -CO-O- or -O-CO-O-, * represents A a21 It is also preferred that the bond is

[0576] L a21 is preferably a single bond, an optionally substituted chain hydrocarbon group of 1 to 12 carbon atoms (provided that -CH2- in the chain hydrocarbon group may be replaced with -O- or -CO-), an optionally substituted cyclic hydrocarbon group of 3 to 20 carbon atoms (provided that -CH2- in the cyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-), or a group formed by combining an optionally substituted chain hydrocarbon group of 1 to 8 carbon atoms with an optionally substituted cyclic hydrocarbon group of 3 to 20 carbon atoms (provided that -CH2- in the chain hydrocarbon group may be replaced with -O- or -CO-, and -CH2- in the cyclic hydrocarbon group may be replaced with -O-, -S-, -SO2- or -CO-). and more preferably, it is a chain hydrocarbon group of 1 to 10 carbon atoms which may have a substituent (provided that -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), a cyclic hydrocarbon group of 3 to 18 carbon atoms which may have a substituent (provided that -CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-), or a group formed by combining a chain hydrocarbon group of 1 to 6 carbon atoms which may have a substituent and a cyclic hydrocarbon group of 3 to 18 carbon atoms which may have a substituent (provided that -CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-, and -CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -S-, -SO2- or -CO-).

[0577] L a22 Examples of the chain hydrocarbon group having 1 to 12 carbon atoms include straight-chain alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, propane-1,2-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl, nonane-1,9-diyl, decane-1,10-diyl, undecane-1,11-diyl, and dodecane-1,12-diyl. and branched alkanediyl groups such as an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-1,2-diyl group, a propane-2,2-diyl group, a 1-methylpropane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a 1-dimethylpropane-1,3-diyl group, a pentane-2,4-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. The number of carbon atoms in the chain hydrocarbon group is preferably 1 to 10, more preferably 1 to 8, even more preferably 1 to 6, and even more preferably 1 to 4.

[0578] L a22 may have one or more fluorine atoms. L a22 The -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and these substituted groups may be in the range of L, as long as the upper limit of the number of carbon atoms allows. a21 Examples include the same as those exemplified above.

[0579] na2 is preferably an integer of 1 to 4, and more preferably an integer of 1 to 3. L a21 When R is a single bond or a chain hydrocarbon group, examples of the structural unit (a2) include the following structural units: a2 A structural unit in which a methyl group corresponding to the following is replaced with a hydrogen atom or the like is also a suitable structural unit of the structural unit (a2), similar to the structural unit below.

[0580] [ka]

[0581] When producing a resist pattern from the resist composition of the present invention, if a high-energy ray such as a KrF excimer laser (248 nm), an electron beam, or EUV (extreme ultraviolet) is used as an exposure light source, the structural unit (a2) preferably has a phenolic hydroxy group, and more preferably the structural unit (a2-A) described below. Furthermore, if an ArF excimer laser (193 nm) or the like is used, the structural unit (a2) preferably has an alcoholic hydroxy group, and more preferably the structural unit (a2-C) described below. The structural unit (a2) may contain one type alone or two or more types.

[0582] In the structural unit (a2), L a21 is a cyclic hydrocarbon group, and examples of the structural unit having a phenolic hydroxy group or a carboxy group include a structural unit represented by formula (a2-A) (hereinafter sometimes referred to as "structural unit (a2-A)").

[0583] [ka]

[0584] [In formula (a2-A), all symbols have the same meanings as defined above.] R a2 and A a21 The groups include the same groups as those exemplified in formula (a2).

[0585] R a27 Examples of the halogen atom include a fluorine atom, an iodine atom, a chlorine atom, and a bromine atom. R a27Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably an alkyl group having 1 to 3 carbon atoms, even more preferably a methyl group or an ethyl group, and even more preferably a methyl group.

[0586] R a27 Examples of the haloalkyl group include a trifluoromethyl group, a difluoromethyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, etc. The number of carbon atoms in the haloalkyl group is preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 to 2.

[0587] R a27 Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a sec-butoxy group, and a tert-butoxy group. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably an alkoxy group having 1 to 3 carbon atoms, even more preferably a methoxy group or an ethoxy group, and even more preferably a methoxy group.

[0588] R a27 Examples of the alkoxyalkyl group include a methoxymethyl group, an ethoxyethyl group, a propoxymethyl group, an isopropoxymethyl group, a butoxymethyl group, a sec-butoxymethyl group, and a tert-butoxymethyl group. The alkoxyalkyl group is preferably an alkoxyalkyl group having 2 to 8 carbon atoms, more preferably an alkoxyalkyl group having 2 to 4 carbon atoms, even more preferably a methoxymethyl group or an ethoxyethyl group, and still more preferably a methoxymethyl group.

[0589] R a27 Examples of the alkoxyalkoxy group include a methoxymethoxy group, a methoxyethoxy group, an ethoxymethoxy group, an ethoxyethoxy group, a propoxymethoxy group, an isopropoxymethoxy group, a butoxymethoxy group, a sec-butoxymethoxy group, and a tert-butoxymethoxy group. The alkoxyalkoxy group is preferably an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably an alkoxyalkoxy group having 2 to 4 carbon atoms, and even more preferably a methoxyethoxy group or an ethoxyethoxy group.

[0590] R a27 Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, a butyryl group, etc. The alkylcarbonyl group is preferably an alkylcarbonyl group having 2 to 4 carbon atoms, more preferably an alkylcarbonyl group having 2 to 3 carbon atoms, and even more preferably an acetyl group.

[0591] R a27 Examples of the alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, and a butyryloxy group. The alkylcarbonyloxy group is preferably an alkylcarbonyloxy group having 2 to 4 carbon atoms, more preferably an alkylcarbonyloxy group having 2 to 3 carbon atoms, and even more preferably an acetyloxy group.

[0592] R a27 is preferably a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 4 carbon atoms which may have a halogen atom, an alkoxy group having 1 to 4 carbon atoms or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group or an ethoxymethoxy group, and even more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group or an ethoxyethoxy group.

[0593] nA2 is preferably 1, 2, 3 or 4, more preferably 1, 2 or 3, and even more preferably 1 or 2. na21 is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, and even more preferably 0 or 1.

[0594] mc is preferably 0 or 1. -X a2 -OH is a benzene ring, A a21 It is preferable that at least one of them is bonded to the m-position or p-position, and more preferable that it is bonded to the m-position. In the case of a naphthalene ring, A a21 When the bonding position of A is the 1st position, it may be bonded to any of the 2nd to 8th positions. a21 When the bonding position of A is the 2nd position, it may be bonded to any of the 1st position and the 3rd to 8th positions. a21 When the bonding position of A is position 1, at least one of A is preferably bonded to position 3 to 6, and more preferably bonded to position 3 or 4. a21 When the bonding position is the 2nd position, it is preferably bonded to the 4th to 7th positions, and more preferably bonded to the 5th or 6th position.

[0595] Examples of the structural unit (a2-A) include structural units derived from monomers described in JP-A Nos. 2010-204634 and 2012-12577. The structural unit (a2-A) may be any of the structural units represented by the formulae (a2-2-1) to (a2-2-32) or (a2-3-1) to (a2-3-24) and the structural units represented by the formulae (a2-2-1) to (a2-2-32) or (a2-3-1) to (a2-3-24), in which R in the structural unit (a2-A) a2 and a structural unit in which the methyl group corresponding to the following formula is replaced with a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group.

[0596] [ka]

[0597] [ka]

[0598] [ka]

[0599] When the structural unit (a2-A) is contained in the resin (A), the content of the structural unit (a2-A) relative to all structural units is, for example, 1 mol% or more, preferably 5 mol% or more, more preferably 10 mol% or more, even more preferably 15 mol% or more, and even more preferably 20 mol% or more. It is also preferably 80 mol% or less, more preferably 70 mol% or less, even more preferably 65 mol% or less, even more preferably 60 mol% or less, even more preferably 50 mol% or less, even more preferably 45 mol% or less, and even more preferably 40 mol% or less. Specifically, it is preferably 5 to 80 mol%, more preferably 10 to 70 mol%, even more preferably 15 to 65 mol%, and even more preferably 20 to 65 mol%.

[0600] The structural unit (a2-A) may be a compound from which the structural unit (a2-A) is derived (e.g., -CH2-C(-R a2 )- is the double bond CH2=C(-R a2 The structural unit (a2-A) can be incorporated into the resin (A) by polymerizing a compound (a2-A') in the state of (a1-4). Alternatively, for example, the structural unit (a1-4) can be polymerized, followed by treatment with an acid such as p-toluenesulfonic acid, to thereby incorporate the structural unit into the resin (A). Alternatively, the structural unit (a2-A) can be polymerized using acetoxystyrene, followed by treatment with an alkali such as tetramethylammonium hydroxide, to thereby incorporate the structural unit into the resin (A).

[0601] In the structural unit (a2), L a21is a cyclic hydrocarbon group, examples of the structural unit having an alcoholic hydroxy group or a carboxy group include a structural unit represented by formula (a2-B) (hereinafter may be referred to as "structural unit (a2-B)"), a structural unit represented by formula (a2-C) (hereinafter may be referred to as "structural unit (a2-C)"), and a structural unit represented by formula (a2-D) (hereinafter may be referred to as "structural unit (a2-D)").

[0602] [ka]

[0603] [In formula (a2-B) and formula (a2-C), R a2 has the same meaning as formula (a2).

[0604] R a27 has the same meaning as formula (a2-A). L a25 is -O- or *-O-(CH2) k2 represents -CO-O-, k2 represents an integer of 1 to 7. * represents the bonding site with —CO—.

[0605] X a2 represents a single bond or -CO-. R a25 and R a26 each independently represents a hydrogen atom, a methyl group, or a hydroxy group.

[0606] nB2 represents an integer of 1 to 5. When nB2 is 2 or more, a plurality of X a2 may be the same or different from each other. nB22 represents an integer of 0 to 8. When nB22 is 2 or more, a plurality of R a27 may be the same or different from each other.

[0607] nC22 represents an integer of 0 to 10. When nC22 is 2 or more, a plurality of R a27may be the same or different from each other. L a25 is preferably —O— or —O—(CH2) f1 It is —CO—O— (wherein f1 represents an integer of 1 to 4), and more preferably —O—.

[0608] R a2 is preferably a methyl group. X a2 is preferably a single bond. R a25 is preferably a hydrogen atom.

[0609] R a26 is preferably a hydrogen atom or a hydroxy group. R a27 is preferably a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 4 carbon atoms which may have a halogen atom, an alkoxy group having 1 to 4 carbon atoms or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group or an ethoxymethoxy group, and even more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group or an ethoxyethoxy group.

[0610] nB2 is preferably 1, 2, 3 or 4, more preferably 1, 2 or 3, and even more preferably 1 or 2. nB22 is preferably an integer of 0 to 3, more preferably 0, 1 or 2, and even more preferably 0 or 1.

[0611] nC22 is preferably an integer of 0 to 6, more preferably an integer of 0 to 3, even more preferably 0, 1 or 2, and even more preferably 0 or 1.

[0612] Examples of the structural unit (a2-B) and the structural unit (a2-C) include structural units derived from monomers described in JP-A-2010-204646, the following structural units, and R in the following structural units: a2 In particular, structural units represented by any one of formulas (a2-B-1) to (a2-B-5) and formulas (a2-C-1) to (a2-C-9) are preferred.

[0613] [ka]

[0614] When the resin (A) contains the structural unit (a2-B) or the structural unit (a2-C), the content thereof, based on the total structural units of the resin (A), can be 1 mol% or more, preferably 2 mol% or more. Alternatively, the content can be 45 mol% or less, preferably 40 mol% or less, more preferably 35 mol% or less, even more preferably 20 mol% or less, and even more preferably 10 mol% or less. Specifically, the content can be 1 to 45 mol%, preferably 1 to 40 mol%, more preferably 1 to 35 mol%, even more preferably 1 to 20 mol%, and even more preferably 1 to 10 mol%.

[0615] [ka]

[0616] [In formula (a2-D), R a2 and A a21 have the same meaning as in formula (a2).

[0617] R a27 has the same meaning as formula (a2-A). R a21 and R a22 each independently represents a fluorinated alkyl group having 1 to 4 carbon atoms. L a24represents a single bond or an alkanediyl group having 1 to 3 carbon atoms, and the alkanediyl group may be substituted with a fluorine atom.

[0618] nD2 represents an integer of 1 to 5. When nD2 is 2 or greater, the groups in the parentheses may be the same or different. nD22 represents an integer of 0 to 4. When nD22 is 2 or more, a plurality of R a27 may be the same or different, provided that 1≦nD2+nD22≦5. R a21 and R a22 Examples of the fluorinated alkyl groups are each independently a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 3,3,3-trifluoropropyl group, a 4,4,4-trifluorobutyl group, and the like.

[0619] R a21 and R a22 As the aryl group, a trifluoromethyl group is preferred. L a24 Examples of the alkanediyl group include a methylene group, an ethane-1,1-diyl group, a propane-1,1-diyl group, and a propane-2,2-diyl group.

[0620] L a24 is preferably a single bond or a methylene group. R a27 is preferably a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 4 carbon atoms which may have a halogen atom, an alkoxy group having 1 to 4 carbon atoms or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group or an ethoxymethoxy group, and even more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group or an ethoxyethoxy group.

[0621] nD2 is preferably 1, 2, 3, or 4, more preferably 1, 2, or 3, even more preferably 1 or 2, and even more preferably 1. Also preferably, nD2 is 1, and the group in parentheses is bonded to the para position.

[0622] nD22 is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, even more preferably 0 or 1, and even more preferably 0. The structural unit (a2-D) is more preferably a structural unit represented by the following formula (a2-D1) (hereinafter, may be referred to as "structural unit (a2-D1)").

[0623] [ka]

[0624] [In formula (a2-D1), R a2 , A a21 , R a27 , nD2 and nD22 have the same meaning as in formula (a2-D). In formula (a2-D1), R a2 is preferably a hydrogen atom or a methyl group.

[0625] A a21 is preferably a single bond. Examples of the structural unit (a2-D) include the structural units shown below.

[0626] [ka]

[0627] In the structural units represented by formulae (a2-D-1) to (a2-D-8), R a2 In the structural units represented by formulas (a2-D-9) to (a2-D-16), the hydrogen atom corresponding to R a2Specific examples of the structural unit (a2-D) include structural units in which the methyl group corresponding to the following formula is replaced with a hydrogen atom, etc. Among these, structural units represented by formulas (a2-D-1) to (a2-D-8) are preferred, structural units represented by formulas (a2-D-1) to (a2-D-4) are more preferred, and structural units represented by formula (a2-D-1) are even more preferred.

[0628] When the resin (A) contains the structural unit (a2-D), its content is preferably 3 mol% or more, more preferably 5 mol% or more, and even more preferably 10 mol% or more, based on the total structural units of the resin (A). It is also preferably 80 mol% or less, more preferably 75 mol% or less, even more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, it is preferably 3 to 80 mol%, more preferably 5 to 75 mol%, even more preferably 10 to 70 mol%, and even more preferably 10 to 65 mol%.

[0629] <Structural unit (a3)> The lactone ring contained in the structural unit (a3) ​​may be a monocyclic ring such as a β-propiolactone ring, a γ-butyrolactone ring, or a δ-valerolactone ring, or a condensed ring of a monocyclic lactone ring with another ring. Preferred examples include a γ-butyrolactone ring, an adamantane lactone ring, or a bridged ring containing a γ-butyrolactone ring structure (for example, a structural unit represented by the following formula (a3-2)).

[0630] The structural unit (a3) ​​is preferably a structural unit represented by formula (a3-1), formula (a3-2), formula (a3-3), or formula (a3-4). One of these may be contained alone, or two or more may be contained.

[0631] [ka]

[0632] [In formula (a3-1), formula (a3-2), formula (a3-3) and formula (a3-4), L a4, L a5 and L a6 are each independently -O- or -O-(CH2) k3 It represents a group represented by —CO—O— (k3 represents an integer of 1 to 7).

[0633] L a7 -O-, *-OL a8 -O-, *-OL a8 -CO-O-, *-OL a8 -CO-OL a9 -CO-O- or *-OL a8 -O-CO-L a9 Represents -O-.

[0634] L a8 and L a9 each independently represents an alkanediyl group having 1 to 6 carbon atoms. * indicates the bonding site with the carbonyl group. R a18 , R a19 , R a20 and R a24 each independently represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom.

[0635] X a3 represents -CH2- or an oxygen atom. R a21 represents an aliphatic hydrocarbon group having 1 to 4 carbon atoms. R a22 , R a23 and R a25 each independently represents a carboxy group, a cyano group, or an aliphatic hydrocarbon group having 1 to 4 carbon atoms.

[0636] p1 represents an integer of 0 to 5. q1 represents an integer of 0 to 3. r1 represents an integer of 0 to 3.

[0637] w1 represents an integer of 0 to 8. When p1, q1, r1 and / or w1 are 2 or more, multiple Ra21 , R a22 , R a23 and / or R a25 may be the same as or different from each other. R a21 , R a22 , R a23 and R a25 Examples of the aliphatic hydrocarbon group in include alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, and a tert-butyl group.

[0638] R a18 , R a19 , R a20 and R a24 Examples of the halogen atom in the formula include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R a18 , R a19 , R a20 and R a24 Examples of the alkyl group in include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group, and preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group or an ethyl group.

[0639] R a18 , R a19 , R a20 and R a24 Examples of the alkyl group having a halogen atom in the formula (I) include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group, a perfluorohexyl group, a trichloromethyl group, a tribromomethyl group, and a triiodomethyl group.

[0640] L a8 and L a9Examples of the alkanediyl group in the formula (I) include a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a butane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group.

[0641] In formulas (a3-1) to (a3-3), L a4 ~L a6 are each independently preferably -O- or -O-(CH2) k3 In -CO-O-, k3 is a group in which k3 is any integer of 1 to 4, more preferably -O- and *-O-CH2-CO-O-, and even more preferably an oxygen atom.

[0642] L a7 is preferably -O- or *-OL a8 It is —CO—O—, and more preferably —O—, —O—CH 2 —CO—O— or —O—C 2 H 4 —CO—O—. R a18 , R a19 , R a20 and R a24 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group.

[0643] R a21 is preferably a methyl group. R a22 , R a23 and R a25 are each independently preferably a carboxy group, a cyano group, or a methyl group.

[0644] p1, q1 and r1 each independently represent an integer of preferably 0 to 2, and more preferably 0 or 1. w1 is preferably an integer of 0 to 2, and more preferably 0 or 1.

[0645] In particular, the formula (a3-4) is preferably the formula (a3-4').

[0646] [ka]

[0647] (In the formula, R a24 , L a7 has the same meaning as above.) Examples of the structural unit (a3) ​​include structural units derived from monomers described in JP 2010-204646 A, JP 2000-122294 A, and JP 2012-41274 A. Examples of the structural unit (a3) ​​include structural units represented by any of formulas (a3-1-1), (a3-1-2), (a3-2-1), (a3-2-2), (a3-3-1), (a3-3-2), and (a3-4-1) to (a3-4-12), and in the structural units, R in formulas (a3-1) to (a3-4) a18 , R a19 , R a20 and R a24 A structural unit in which a methyl group corresponding to the following is replaced with a hydrogen atom is preferred.

[0648] [ka]

[0649] When the resin (A) contains the structural unit (a3), the total content thereof, based on all structural units in the resin (A), can be 1 mol% or more, preferably 3 mol% or more, more preferably 5 mol% or more, and even more preferably 10 mol% or more. It can also be 70 mol% or less, preferably 65 mol% or less, more preferably 60 mol% or less, even more preferably 50 mol% or less, still more preferably 40 mol% or less, even more preferably 30 mol% or less, still more preferably 25 mol% or less, and even more preferably 20 mol% or less. Specifically, it can be 1 to 70 mol%, preferably 3 to 70 mol%, more preferably 3 to 65 mol%, even more preferably 5 to 65 mol%, even more preferably 5 to 60 mol%, and even more preferably 10 to 60 mol%.

[0650] Furthermore, the content of the structural unit (a3-1), the structural unit (a3-2), the structural unit (a3-3), or the structural unit (a3-4) is preferably 1 mol% or more, more preferably 3 mol% or more, even more preferably 5 mol% or more, and even more preferably 10 mol% or more, based on the total structural units of the resin (A). It is also preferably 60 mol% or less, more preferably 55 mol% or less, even more preferably 50 mol% or less, still more preferably 40 mol% or less, even more preferably 30 mol% or less, still more preferably 25 mol% or less, and even more preferably 20 mol% or less. Specifically, it is preferably 1 to 60 mol%, more preferably 3 to 60 mol%, even more preferably 3 to 55 mol%, even more preferably 5 to 55 mol%, even more preferably 5 to 50 mol%, and even more preferably 10 to 50 mol%.

[0651] <Structural unit (a4)> The structural unit represented by formula (a4) is shown below.

[0652] [ka]

[0653] [In formula (a4), R 41 represents a hydrogen atom or a methyl group.

[0654] R 42 represents an aliphatic hydrocarbon group having 1 to 48 carbon atoms and containing a halogen atom, and -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-.] R 42 Examples of the aliphatic hydrocarbon group represented by the formula (I) include linear or branched chain hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, and groups formed by combining these groups.

[0655] Examples of the chain hydrocarbon group include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl, pentadecyl, hexadecyl, heptadecyl, and octadecyl groups, and branched alkyl groups such as isopropyl and isobutyl groups.

[0656] Examples of the monocyclic or polycyclic alicyclic hydrocarbon group include monocyclic alicyclic hydrocarbon groups which are monocyclic cycloalkyl groups such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group; and polycyclic alicyclic hydrocarbon groups which are polycyclic cycloalkyl groups such as a decahydronaphthyl group, an adamantyl group, a norbornyl group, and the following groups (* indicates a bonding site):

[0657] [ka]

[0658] Examples of groups formed by combination include groups formed by combining one or more alkyl groups or one or more alkanediyl groups with one or more alicyclic hydrocarbon groups, such as -alkanediyl group-alicyclic hydrocarbon group, -alicyclic hydrocarbon group-alkyl group, and -alkanediyl group-alicyclic hydrocarbon group-alkyl group.

[0659] Examples of the alkanediyl group include linear alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl; and branched alkanediyl groups such as propane-1,2-diyl, butane-1,3-diyl, 2-methylpropane-1,2-diyl, 1-methylbutane-1,4-diyl, and 2-methylbutane-1,4-diyl. The terminal of the branched alkanediyl group may be a methyl group.

[0660] R 42 Examples of the halogen atom contained in the aliphatic hydrocarbon group include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R 42 Examples of the aliphatic hydrocarbon group in which -CH- is replaced with -O- or -CO- include a hydroxy group, a carboxy group, a carbonyl group, an oxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkanediyloxy group, an alkanediyloxycarbonyl group, an alkanediylcarbonyl group, an alkanediylcarbonyloxy group, a cycloalkoxy group, a cycloalkylalkoxy group, and a group combining two or more of these groups. These substituted groups include the same groups as exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms.

[0661] The structural unit (a4) is R 42 is preferably an aliphatic hydrocarbon group having a fluorine atom. 42 However, examples of the structural unit (a4) that is an aliphatic hydrocarbon group having a fluorine atom include a structural unit represented by formula (a4-1) (hereinafter, may be referred to as "structural unit (a4-1)"), a structural unit represented by formula (a4-2) (hereinafter, may be referred to as "structural unit (a4-2)"), a structural unit represented by formula (a4-3) (hereinafter, may be referred to as "structural unit (a4-3)"), and a structural unit represented by formula (a4-A) (hereinafter, may be referred to as "structural unit (a4-A)").

[0662] The structural unit represented by formula (a4-1) is a structural unit represented by the following formula:

[0663] [ka]

[0664] [In formula (a4-1), R 41 represents a hydrogen atom or a methyl group.

[0665] L 41 represents a single bond or an alkanediyl group having 1 to 4 carbon atoms. L 42f represents a fluorine atom-containing alkanediyl group having 1 to 8 carbon atoms or a fluorine atom-containing cycloalkanediyl group having 3 to 12 carbon atoms.

[0666] R 42f represents a hydrogen atom or a fluorine atom. L 41 Examples of the alkanediyl group in the formula (I) include linear alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, and butane-1,4-diyl, and branched alkanediyl groups such as ethane-1,1-diyl, propane-1,2-diyl, butane-1,3-diyl, 2-methylpropane-1,3-diyl, and 2-methylpropane-1,2-diyl. The terminal of the branched alkanediyl group may be a methyl group.

[0667] L 42f Examples of the alkanediyl group having a fluorine atom in the formula (I) include a linear alkanediyl group having a fluorine atom, such as a methylene group having a fluorine atom, an ethylene group having a fluorine atom, a propane-1,3-diyl group having a fluorine atom, a butane-1,4-diyl group having a fluorine atom, a pentane-1,5-diyl group having a fluorine atom, a hexane-1,6-diyl group having a fluorine atom, a heptane-1,7-diyl group having a fluorine atom, and an octane-1,8-diyl group having a fluorine atom; Examples of branched alkanediyl groups having fluorine atoms include ethane-1,1-diyl groups having fluorine atoms, propane-1,1-diyl groups having fluorine atoms, propane-1,2-diyl groups having fluorine atoms, propane-2,2-diyl groups having fluorine atoms, pentane-2,4-diyl groups having fluorine atoms, 2-methylpropane-1,3-diyl groups having fluorine atoms, 2-methylpropane-1,2-diyl groups having fluorine atoms, pentane-1,4-diyl groups having fluorine atoms, and 2-methylbutane-1,4-diyl groups having fluorine atoms. The terminal of the branched alkanediyl group may be a methyl group which may have a fluorine atom.

[0668] L 42f Examples of the cycloalkanediyl group having a fluorine atom in the formula (I) include monocyclic cycloalkanediyl groups having a fluorine atom, such as a cyclobutane-1,3-diyl group having a fluorine atom, a cyclopentane-1,3-diyl group having a fluorine atom, a cyclohexane-1,4-diyl group having a fluorine atom, a cyclohexene-3,6-diyl group having a fluorine atom, a cycloheptane-1,4-diyl group having a fluorine atom, and a cyclooctane-1,5-diyl group having a fluorine atom; Examples of polycyclic cycloalkanediyl groups having a fluorine atom include a norbornane-1,4-diyl group having a fluorine atom, a norbornane-2,5-diyl group having a fluorine atom, a 5-norbornene-2,3-diyl group having a fluorine atom, an adamantane-1,5-diyl group having a fluorine atom, and an adamantane-2,6-diyl group having a fluorine atom.

[0669] L 42f The number of fluorine atoms contained in the alkanediyl group and cycloalkanediyl group having a fluorine atom in the formula (I) may be 1 or more, and is preferably 2 or more. L 42f The alkanediyl group and cycloalkanediyl group having a fluorine atom in the formula (I) are preferably a perfluoroalkanediyl group and a perfluorocycloalkanediyl group, respectively.

[0670] L42f Examples of the perfluoroalkanediyl group in the formula (I) include a difluoromethylene group, a perfluoroethylene group, a perfluoroethylfluoromethylene group, a perfluoropropane-1,3-diyl group, a perfluoropropane-1,2-diyl group, a perfluoropropane-2,2-diyl group, a perfluorobutane-1,4-diyl group, a perfluorobutane-2,2-diyl group, a perfluorobutane-1,2-diyl group, a perfluoropentane-1,5-diyl group, a perfluoropentane-2,2-diyl group, a perfluoropentane-3 ,3-diyl group, perfluorohexane-1,6-diyl group, perfluorohexane-2,2-diyl group, perfluorohexane-3,3-diyl group, perfluoroheptane-1,7-diyl group, perfluoroheptane-2,2-diyl group, perfluoroheptane-3,4-diyl group, perfluoroheptane-4,4-diyl group, perfluorooctane-1,8-diyl group, perfluorooctane-2,2-diyl group, perfluorooctane-3,3-diyl group, and perfluorooctane-4,4-diyl group.

[0671] L 42f Examples of the perfluorocycloalkanediyl group in the formula (I) include a perfluorocyclohexanediyl group, a perfluorocyclopentanediyl group, a perfluorocycloheptanediyl group, and a perfluoroadamantanediyl group.

[0672] L 41 is preferably a single bond or an alkanediyl group having 1 to 3 carbon atoms, more preferably a single bond, a methylene group or an ethylene group, and even more preferably a single bond or a methylene group.

[0673] L 42f is preferably a perfluoroalkanediyl group having 1 to 8 carbon atoms or a perfluorocycloalkanediyl group having 3 to 12 carbon atoms, more preferably a perfluoroalkanediyl group having 1 to 6 carbon atoms, and even more preferably a perfluoroalkanediyl group having 1 to 3 carbon atoms.

[0674] The structural unit (a4-1) includes the structural units shown below and R in the structural unit (a4-1) in the structural units shown below. 41 The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example.

[0675] [ka]

[0676] The structural unit represented by formula (a4-2) is a structural unit shown below.

[0677] [ka]

[0678] [In formula (a4-2), R 41 represents a hydrogen atom or a methyl group.

[0679] L 43f represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may contain a fluorine atom, and -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-. R 43f represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a fluorine atom, and -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-.

[0680] However, L 43f and R 43f At least one of L has a fluorine atom, 43f and R 43f The maximum total number of carbon atoms is 21. L 43f and R 43f Examples of the aliphatic hydrocarbon group in L include linear or branched chain hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, and groups formed by combining these groups. 43f and R 43f Examples of the aliphatic hydrocarbon group in43f and R 43f As long as the upper limit of the total number of carbon atoms in 42 Examples of the aliphatic hydrocarbon group include the same groups as the exemplified aliphatic hydrocarbon groups.

[0681] L 43f The aliphatic hydrocarbon group is preferably an alkanediyl group having 1 to 6 carbon atoms or a group represented by formula (L43f-1).

[0682] [ka]

[0683] [In formula (L43f-1), s represents 0 or 1.

[0684] L 45f and L 46f each independently represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may contain a fluorine atom. L 47f represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may contain a fluorine atom.

[0685] X 46f and X 47f each independently represents -O-, -CO-, -CO-O- or -O-CO-. However, L 45f , L 46f , L 47f , X 46f and X 47f The total number of carbon atoms is 7 or less.

[0686] * and ** are binding sites, and ** is -O-CO-R 43f ] L in the group represented by formula (L43f-1) 45f , L 46f and L 47fExamples of the divalent aliphatic hydrocarbon group represented by include a linear or branched alkanediyl group, a monocyclic or polycyclic divalent alicyclic hydrocarbon group, and a divalent aliphatic hydrocarbon group formed by combining an alkanediyl group with a divalent alicyclic hydrocarbon group. Specific examples include a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a 1-methylpropane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, and a 2-methylpropane-1,2-diyl group.

[0687] Preferably, s is 0. Examples of the group represented by formula (L43f-1) include the following groups: In the following examples, * and ** each represent a bonding site, and ** represents -O-CO-R 43f This is the binding site for

[0688] [ka]

[0689] R 43f is preferably an aliphatic hydrocarbon group having a fluorine atom. In this case, examples of the structural unit represented by formula (a4-2) include structural units represented by formula (a4-2A) or (a4-2B).

[0690] [ka]

[0691] [In formula (a4-2A) and formula (a4-2B), R 41 and L 43f represents the same as in formula (a4-2).

[0692] R 43fA represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms and containing a fluorine atom. A 43frepresents a divalent aliphatic hydrocarbon group having 1 to 17 carbon atoms which may have a fluorine atom, and -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-.

[0693] X 43 represents **-O-CO- or **-CO-O-, and ** represents A 43f represents the binding site with R 43fB represents an aliphatic hydrocarbon group having 1 to 17 carbon atoms which may contain a fluorine atom.

[0694] However, in formula (a4-2A), L 43f and R 43fA The total number of carbon atoms in formula (a4-2B) is 21 or less, and in formula (a4-2B), L 43f , A 43f , X 43 and R 43fB The total number of carbon atoms in A is 21 or less. 43f and R 43fB At least one of them has at least one fluorine atom.] R 43fA The aliphatic hydrocarbon group of R in formula (a4) is as long as the upper limit of the number of carbon atoms permits. 42 Examples of the aliphatic hydrocarbon groups include the same aliphatic hydrocarbon groups as those exemplified above.

[0695] R 43fA is preferably an alkyl group having 1 to 13 carbon atoms and containing a fluorine atom, a cycloalkyl group having 3 to 12 carbon atoms and containing a fluorine atom, or a group combining these, and *-(CF2) n43f -R 42′ (* represents the bonding site with the carbonyl group. n43f represents an integer of 1 to 6. R 42′ represents a hydrogen atom or a fluorine atom.) or a perfluorocycloalkyl group having 3 to 12 carbon atoms is more preferred.

[0696] A 43f and R 43fB The aliphatic hydrocarbon group of R in formula (a4) is as long as the upper limit of the number of carbon atoms permits. 42Examples of the aliphatic hydrocarbon groups include the same aliphatic hydrocarbon groups as those exemplified above. A 43f is preferably a divalent chain hydrocarbon group which may have a fluorine atom, a divalent alicyclic hydrocarbon group, or a combination thereof, more preferably a divalent chain hydrocarbon group which has a fluorine atom, and even more preferably a fluorinated alkanediyl group having 1 to 6 carbon atoms.

[0697] R 43fB The aliphatic hydrocarbon group which may have a fluorine atom is preferably a chain hydrocarbon group which may have a fluorine atom, an alicyclic hydrocarbon group or a group combining these, more preferably an alkyl group having 1 to 12 carbon atoms which may have a fluorine atom, a cycloalkyl group having 3 to 12 carbon atoms or a group combining these, and more preferably a trifluoromethyl group, a difluoromethyl group, a methyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, an ethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a propyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluoropropyl group, a ... More preferred are fluorinated alkyl groups such as nonafluorobutyl, butyl, perfluoropentyl, 2,2,3,3,4,4,5,5,5-nonafluoropentyl, pentyl, hexyl, perfluorohexyl, heptyl, perfluoroheptyl, octyl, and perfluorooctyl groups, cyclopropylmethyl, cyclopropyl, cyclobutylmethyl, cyclopentyl, cyclohexyl, perfluorocyclohexyl, adamantyl, adamantylmethyl, adamantyldimethyl, norbornyl, norbornylmethyl, perfluoroadamantyl, and perfluoroadamantylmethyl groups.

[0698] In formula (a4-2B), *-A 43f -X 43 -R 43fB An example of a structure that the group represented by the formula (I) can take is the following structure (* indicates the bonding site with the carbonyl group).

[0699] [ka]

[0700] The structural unit represented by formula (a4-2A) includes the structural units shown below and R in the structural unit represented by formula (a4-2A) in the structural units shown below. 41 The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example.

[0701] [ka]

[0702] The structural unit represented by formula (a4-2B) includes the structural units shown below and R in the structural unit represented by formula (a4-2B) in the structural units shown below. 41 The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example.

[0703] [ka]

[0704] The structural unit (a4) also includes a structural unit represented by formula (a4-3).

[0705] [ka]

[0706] [In formula (a4-3), R 41 represents a hydrogen atom or a methyl group.

[0707] L 44f represents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may contain a fluorine atom, and -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-. R 44frepresents an aliphatic hydrocarbon group having 1 to 20 carbon atoms which may contain a fluorine atom, and -CH2- contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-.

[0708] However, L 44f and R 44f At least one of L has a fluorine atom, 44f and R 44f The maximum total number of carbon atoms is 21. L 44f and R 44f Examples of the aliphatic hydrocarbon group in L include linear or branched chain hydrocarbon groups, monocyclic or polycyclic alicyclic hydrocarbon groups, and groups formed by combining these groups. 44f and R 44f Examples of the aliphatic hydrocarbon group in 44f and R 44f As long as the upper limit of the total number of carbon atoms in 42 Examples of the aliphatic hydrocarbon group include the same groups as the exemplified aliphatic hydrocarbon groups.

[0709] L 44f is preferably an alkanediyl group having 1 to 14 carbon atoms (-CH2- contained in the alkanediyl group may be replaced by -O- or -CO-), and -(CH2) j1 -, -(CH2) j2 -O-(CH2) j3 -or-(CH2) j4 -CO-O-(CH2) j5 - (j1 to j5 each independently represent an integer of 1 to 6.) It is more preferable that it is an alkanediyl group having 1 to 4 carbon atoms (one -CH2- contained in the alkanediyl group may be replaced with -O-, and one -CH2-CH2- contained in the alkanediyl group may be replaced with -CO-O- or -O-CO-).

[0710] R 44fis preferably an aliphatic hydrocarbon group having 1 to 10 carbon atoms and having a fluorine atom, more preferably an alkyl group having 1 to 10 carbon atoms and having a fluorine atom, an alicyclic hydrocarbon group having 3 to 10 carbon atoms and having a fluorine atom, or a group combining these, further preferably an alkyl group having 1 to 10 carbon atoms and having a fluorine atom, and even more preferably an alkyl group having 1 to 6 carbon atoms and having a fluorine atom.

[0711] Examples of the structural unit represented by formula (a4-3) include the following structural units and structural units represented by the following formulas: 41 The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example.

[0712] [ka]

[0713] Examples of the structural unit (a4) include a structural unit represented by formula (a4-A).

[0714] [ka]

[0715] [In formula (a4-A), R 44 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom.

[0716] X 44 represents a single bond or *-CO-O-. * represents R 44 represents the bonding site with the carbon atom to which it is bonded. L 44 represents an aliphatic hydrocarbon group having 1 to 28 carbon atoms which may have a substituent, and -CH2- contained in the aliphatic hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-.

[0717] R 45 represents a fluorinated alkyl group having 1 to 8 carbon atoms. R 46 represents a hydrogen atom or a fluorinated alkyl group having 1 to 6 carbon atoms, and the fluorinated alkyl group is L 44 may bond to form an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-.

[0718] mi represents an integer of 1 to 4. When mi is 2 or more, the groups in the parentheses may be the same or different.] R 44 Examples of the halogen atom and the alkyl group optionally having a halogen atom in the formula (a1-0) to the formula (a1-2) include R a01 , R a4 and R a5 Examples include the same as those exemplified above.

[0719] R 44 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, further preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group.

[0720] L 44 Examples of the aliphatic hydrocarbon group in include chain hydrocarbon groups and monocyclic or polycyclic (including spiro rings, fused rings, bridged rings, etc.) alicyclic hydrocarbon groups, and may also be groups that combine two or more of these groups (for example, a hydrocarbon group formed from an alicyclic hydrocarbon group and a chain hydrocarbon group).

[0721] Examples of the chain hydrocarbon group include divalent to pentavalent chain hydrocarbon groups such as an alkanediyl group, an alkanetriyl group, an alkanetetrayl group, and an alkanpentyl group. Examples of the alkanediyl group include linear alkanediyl groups such as methylene, ethylene, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl, nonane-1,9-diyl, decane-1,10-diyl, undecane-1,11-diyl, dodecane-1,12-diyl, tridecane-1,13-diyl, tetradecane-1,14-diyl, pentadecane-1,15-diyl, hexadecane-1,16-diyl, and heptadecane-1,17-diyl groups; Examples of branched alkanediyl groups include an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-1,2-diyl group, a propane-2,2-diyl group, a pentane-2,4-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group.

[0722] Further examples include groups in which one or more hydrogen atoms of the above groups are replaced with bonding sites. The number of carbon atoms in the chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 12, even more preferably 1 to 10, still more preferably 1 to 9, even more preferably 1 to 8, still more preferably 1 to 6, even more preferably 1 to 5, and particularly preferably 1 to 4.

[0723] Examples of the monocyclic or polycyclic alicyclic hydrocarbon group include the following alicyclic hydrocarbon groups: The binding site can be any position.

[0724] [ka]

[0725] For example, divalent to pentavalent alicyclic hydrocarbon groups such as a cycloalkanediyl group, a cycloalkanetriyl group, a cycloalkanetetrayl group, and a cycloalkanepentyl group can be mentioned.

[0726] Specifically, monocyclic alicyclic hydrocarbon groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclooctane-1,5-diyl group, and the like; Examples include cycloalkanediyl groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, decahydronaphthalenediyl group, bicyclo[3.3.0]octanediyl group, spirocyclohexane-1,2'-cyclopentane-diyl group, and spiroadamantane-2,3'-cyclopentane-diyl group; and polycyclic alicyclic hydrocarbon groups such as spiro rings having cycloalkanediyl groups bonded to norbornanediyl groups or adamantanediyl groups via spiro bonds.

[0727] Further examples include groups in which one or more hydrogen atoms of the above groups are replaced with bonding sites. The alicyclic hydrocarbon group preferably has 3 to 20 carbon atoms, more preferably 3 to 18 carbon atoms, even more preferably 3 to 16 carbon atoms, and even more preferably 3 to 12 carbon atoms.

[0728] Examples of groups that combine two or more types include groups that combine an alicyclic hydrocarbon group and a chain hydrocarbon group. In the combination, two or more types of alicyclic hydrocarbon groups and chain hydrocarbon groups may be combined. In addition, when any of the groups is X 44 may be bound to

[0729] Examples of groups combining an alicyclic hydrocarbon group and a chain hydrocarbon group include a group in which an alicyclic hydrocarbon group is bonded to a chain hydrocarbon group (e.g., *-chain hydrocarbon group-alicyclic hydrocarbon group-, etc.), a group in which a chain hydrocarbon group is bonded to an alicyclic hydrocarbon group (e.g., *-alicyclic hydrocarbon group-chain hydrocarbon group-, etc.), a group in which an alicyclic hydrocarbon group and a chain hydrocarbon group are bonded to a chain hydrocarbon group (e.g., *-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-, etc.), a group in which a chain hydrocarbon group and an alicyclic hydrocarbon group are bonded to an alicyclic hydrocarbon group (e.g., *-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-, etc.), Examples of such a group include a group having a hydrocarbon group bonded thereto (for example, *-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-, etc.), a group having an alicyclic hydrocarbon group, a chain hydrocarbon group, and an alicyclic hydrocarbon group bonded to a chain hydrocarbon group (for example, *-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-, etc.), and a group having an alicyclic hydrocarbon group, a chain hydrocarbon group, and a chain hydrocarbon group bonded to an alicyclic hydrocarbon group (for example, *-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-, etc.).

[0730] * is X 44 represents the binding site with Further examples include groups in which one or more hydrogen atoms of the above groups are replaced with bonding sites. L 44 -CH2- contained in the aliphatic hydrocarbon group having 1 to 28 carbon atoms may be replaced with -O-, -S-, -SO2- or -CO-.

[0731] L 44 When —CH2— contained in the aliphatic hydrocarbon group having 1 to 28 carbon atoms is replaced with —O—, —S—, —SO2— or —CO—, the number of carbon atoms before replacement is regarded as the number of carbon atoms of the aliphatic hydrocarbon group.

[0732] Examples of groups in which -CH- in an aliphatic hydrocarbon group is replaced with -O-, -S-, -SO-, or -CO- include a hydroxy group, a carboxy group, a thiol group, an alkoxy group, an alkylthio group, an alkoxycarbonyl group, an alkylsulfonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an oxy group, a carbonyl group, a thio group, a sulfonyl group, an alkanediyloxy group, an alkanediyloxycarbonyl group, an alkanediylcarbonyl group, an alkanediylcarbonyloxy group, an alkanediylsulfonyl group, an alkanediylthio group, a cycloalkoxy group, a cycloalkylalkoxy group, an alkoxycarbonyloxy group, and groups in which two or more of these groups are combined. Examples of these substituted groups include the same groups as those exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms.

[0733] Further examples include groups in which one or more hydrogen atoms of the above groups are replaced with bonding sites. Furthermore, examples of groups in which -CH2- in an alicyclic hydrocarbon group is replaced with -O-, -S-, -CO- or -SO2- include the same groups as exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms.

[0734] L 44 The aliphatic hydrocarbon group in may have one or more substituents, such as a halogen atom, a haloalkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms (wherein -CH2- in the alkyl group or the alicyclic hydrocarbon group may be replaced by -O- or -CO-).

[0735] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of haloalkyl groups having 1 to 4 carbon atoms include fluorinated alkyl groups having 1 to 4 carbon atoms, chlorinated alkyl groups having 1 to 4 carbon atoms, brominated alkyl groups having 1 to 4 carbon atoms, and iodinated alkyl groups having 1 to 4 carbon atoms. Examples of haloalkyl groups include perfluoroalkyl groups having 1 to 4 carbon atoms (such as trifluoromethyl, pentafluoroethyl, heptafluoropropyl, and nonafluorobutyl), 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 4,4,4-trifluorobutyl, 3,3,4,4,4-pentafluorobutyl, chloromethyl, bromomethyl, and iodomethyl. The number of carbon atoms in the haloalkyl group is preferably 1 to 3, and more preferably 1 or 2.

[0736] Examples of the alkyl group having 1 to 12 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, etc. The number of carbon atoms in the alkyl group is preferably 1 to 9, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3.

[0737] Examples of the alicyclic hydrocarbon group having 3 to 18 carbon atoms include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and cyclodecyl, and polycyclic cycloalkyl groups such as decahydronaphthyl, adamantyl, and norbornyl. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 16, more preferably 3 to 12, and even more preferably 3 to 10.

[0738] Examples of aromatic hydrocarbon groups having 6 to 18 carbon atoms include a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a phenanthryl group, a binaphthyl group, etc. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 14, more preferably 6 to 12, and even more preferably 6 to 10.

[0739] When -CH2- in an alkyl group is replaced with -O- or -CO-, the number of carbon atoms before the replacement is counted as the total number of carbon atoms in the alkyl group. Examples of the substituted group include a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, and an alkylcarbonyloxy group. These substituted groups include the same groups as those exemplified in this specification, within the range permitted by the upper limit of the carbon number.

[0740] The alkoxy group preferably has 1 to 9 carbon atoms, more preferably 1 to 6 carbon atoms, even more preferably 1 to 4 carbon atoms, and even more preferably 1 to 3 carbon atoms. The alkoxycarbonyl group has preferably 2 to 9 carbon atoms, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. The alkylcarbonyl group has preferably 2 to 10 carbon atoms, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3. The alkylcarbonyloxy group has preferably 2 to 9 carbon atoms, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 or 3.

[0741] Furthermore, examples of groups in which -CH2- in an alicyclic hydrocarbon group is replaced with -O- or -CO- include the same groups as those exemplified in this specification, within the range permitted by the upper limit of the number of carbon atoms.

[0742] L 44The substituent that the aliphatic hydrocarbon group in the formula (I) may have is preferably a halogen atom, a haloalkyl group having 1 to 3 carbon atoms, an alkyl group having 1 to 6 carbon atoms, an alicyclic hydrocarbon group having 3 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms (-CH2- contained in the alkyl group or the alicyclic hydrocarbon group may be replaced with -O- or -CO-), more preferably a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 3 carbon atoms, or an alkyl group having 1 to 4 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-), and even more preferably a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, a hydroxy group, or a methoxy group.

[0743] L 44 is R 46When the fluorinated alkyl group does not form an alicyclic hydrocarbon group with the fluorinated alkyl group, the alicyclic hydrocarbon group is a chain hydrocarbon group of 1 to 12 carbon atoms which may have a substituent (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), an alicyclic hydrocarbon group of 3 to 18 carbon atoms which may have a substituent (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O- or -CO-), or a chain hydrocarbon group of 1 to 6 carbon atoms which may have a substituent and an alicyclic hydrocarbon group of 3 to 18 carbon atoms which may have a substituent. and a group formed by combining a hydrocarbon group with a hydroxyl group (-CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-, and -CH2- contained in the alicyclic hydrocarbon group may be replaced with -O- or -CO-), and examples thereof include a chain hydrocarbon group having 1 to 8 carbon atoms which may have a substituent (-CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), an alicyclic hydrocarbon group having 3 to 12 carbon atoms which may have a substituent, or a group formed by combining a hydrocarbon group with a hydroxyl group with a hydroxyl group (-CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-). It is more preferably a group formed by combining a chain hydrocarbon group of 1 to 6 carbon atoms with an alicyclic hydrocarbon group of 3 to 18 carbon atoms which may have a substituent (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), and examples thereof include a chain hydrocarbon group of 1 to 8 carbon atoms which may have a substituent (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-), an alicyclic hydrocarbon group of 5 to 12 carbon atoms which may have a substituent, a chain hydrocarbon group of 1 to 6 carbon atoms and More preferably, it is a group formed by combining an alicyclic hydrocarbon group of 5 to 12 carbon atoms which may have a substituent (-CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-), or a group formed by combining an alicyclic hydrocarbon group of 5 to 12 carbon atoms which may have a substituent, a chain hydrocarbon group of 1 to 6 carbon atoms, and an alicyclic hydrocarbon group of 5 to 12 carbon atoms which may have a substituent (-CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-).

[0744] R 45Examples of the fluorinated alkyl group having 1 to 8 carbon atoms in the formula (I) include a difluoromethyl group, a trifluoromethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a perfluoroethyl group, a 1,1,2,2-tetrafluoropropyl group, a 1,1,2,2,3,3-hexafluoropropyl group, a perfluoroethylmethyl group, a 1-(trifluoromethyl)-1,2,2,2-tetrafluoroethyl group, a perfluoropropyl group, a 1,1,2,2-tetrafluorobutyl group, a 1,1,2,2,3,3-hexafluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a perfluorobutyl group, a 1,1-bis(trifluoro)methyl group, a Examples of the fluorinated alkyl group include 2,2,2-trifluoroethyl, 2-(perfluoropropyl)ethyl, 1,1,2,2,3,3,4,4-octafluoropentyl, perfluoropentyl, 1,1,2,2,3,3,4,4,5,5-decafluoropentyl, 1,1-bis(trifluoromethyl)-2,2,3,3,3-pentafluoropropyl, perfluoropentyl, 2-(perfluorobutyl)ethyl, 1,1,2,2,3,3,4,4,5,5-decafluorohexyl, 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluorohexyl, perfluoropentylmethyl, perfluorohexyl, perfluoroheptyl, and perfluorooctyl. The number of carbon atoms in the fluorinated alkyl group is preferably 1 to 6, more preferably 1 to 5, even more preferably 1 to 4, and even more preferably 1 to 3.

[0745] R 46 The fluorinated alkyl group having 1 to 6 carbon atoms in R is as large as possible within the upper limit of the carbon number. 45 The same fluorinated alkyl groups having 1 to 6 carbon atoms as those given as examples of the fluorinated alkyl groups in the above can also be used.

[0746] R 45 is R 46When is a fluorinated alkyl group having 1 to 6 carbon atoms, it is preferably a fluorinated alkyl group having 1 to 6 carbon atoms, more preferably a fluorinated alkyl group having 1 to 3 carbon atoms, even more preferably a trifluoromethyl group, a perfluoroethyl group or a perfluoropropyl group, and even more preferably a trifluoromethyl group.

[0747] R 45 is R 46 When is a hydrogen atom, it is preferably a fluorinated alkyl group having 1 to 6 carbon atoms, more preferably a fluorinated alkyl group having 1 to 5 carbon atoms, and even more preferably a fluorinated alkyl group having 3 to 5 carbon atoms.

[0748] R 46 L 44 When R is bonded to form an alicyclic hydrocarbon group having 3 to 12 carbon atoms, 46 L 44 Examples of groups formed by bonding with include groups represented by the following formulae: In the following formulae, * and ** represent bonding sites, and one of the two ** represents a bonding site with a hydroxy group and the other represents a bonding site with R 45 represents the binding site with L 44A L 44 R is a part of the hydrocarbon group and represents a single bond or an alkanediyl group having 1 to 4 carbon atoms. 46 L 44 The alicyclic hydrocarbon group formed by bonding with the above preferably has 3 to 10 carbon atoms, more preferably 3 to 8 carbon atoms, and even more preferably 3 to 6 carbon atoms.

[0749] [ka]

[0750] R 46 is preferably a hydrogen atom or a fluorinated alkyl group having 1 to 3 carbon atoms. mi is preferably an integer of 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0751] Examples of the structural unit (a4-A) include the following structural units. In these structural units, R 44 and structural units in which the methyl group corresponding to R is replaced by a hydrogen atom, a halogen atom, a haloalkyl group, or an alkyl group other than a methyl group. 44 Specific examples of the structural unit (a4-A) include structural units in which the hydrogen atom corresponding to the following is replaced with a halogen atom, a haloalkyl group, or an alkyl group.

[0752] [ka]

[0753] When the resin (A) or the like contains the structural unit (a4), the content thereof is preferably 1 to 20 mol %, more preferably 2 to 15 mol %, and even more preferably 3 to 10 mol %, based on all structural units in the resin (A) or the like.

[0754] <Structural unit (a5)> The non-leaving hydrocarbon group contained in the structural unit (a5) may be a group containing a linear, branched, or cyclic hydrocarbon group, and among these, the structural unit (a5) is preferably a group containing an alicyclic hydrocarbon group.

[0755] Examples of the structural unit (a5) include a structural unit represented by formula (a5-1).

[0756] [ka]

[0757] [In formula (a5-1), R 51 represents a hydrogen atom or a methyl group.

[0758] R 52 represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms, and a hydrogen atom contained in the alicyclic hydrocarbon group may be substituted with an aliphatic hydrocarbon group having 1 to 8 carbon atoms. L 55represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-.] R 52 The alicyclic hydrocarbon group in may be either monocyclic or polycyclic. Examples of monocyclic alicyclic hydrocarbon groups include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Examples of polycyclic alicyclic hydrocarbon groups include adamantyl and norbornyl.

[0759] Examples of the aliphatic hydrocarbon group having 1 to 8 carbon atoms include alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, octyl, and 2-ethylhexyl.

[0760] Examples of the alicyclic hydrocarbon group having a substituent include a 3-methyladamantyl group. R 52 is preferably an unsubstituted alicyclic hydrocarbon group having 3 to 18 carbon atoms, and more preferably an adamantyl group, a norbornyl group, or a cyclohexyl group.

[0761] L 55 The divalent saturated hydrocarbon group in the formula (I) includes a divalent saturated chain hydrocarbon group and a divalent saturated alicyclic hydrocarbon group, and is preferably a divalent saturated chain hydrocarbon group. Examples of the divalent chain saturated hydrocarbon group include a methylene group, an ethylene group, and an alkanediyl group such as a propanediyl group, a butanediyl group, and a pentanediyl group.

[0762] The divalent alicyclic saturated hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic saturated hydrocarbon group include cycloalkanediyl groups such as cyclopentanediyl and cyclohexanediyl. Examples of the polycyclic divalent alicyclic saturated hydrocarbon group include adamantanediyl and norbornanediyl.

[0763] L 55 Examples of the divalent saturated hydrocarbon group represented by formula (L1-1) in which one -CH2- is replaced with -O- or -CO- include groups represented by formula (L1-1) to formula (L1-4). In the following formulae, * and ** each represent a bonding site, and * represents a bonding site to an oxygen atom.

[0764] [ka]

[0765] [In formula (L1-1), X x1 represents *-O-CO- or *-CO-O- (* represents L x1 represents the binding site with ).

[0766] L x1 represents a divalent aliphatic saturated hydrocarbon group having 1 to 16 carbon atoms. L x2 represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 15 carbon atoms. However, L x1 and L x2 The total number of carbon atoms is 16 or less.

[0767] In formula (L1-2), L x3 represents a divalent aliphatic saturated hydrocarbon group having 1 to 17 carbon atoms. L x4 represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 16 carbon atoms.

[0768] However, L x3 and L x4 The total number of carbon atoms is 17 or less. In formula (L1-3), L x5 represents a divalent aliphatic saturated hydrocarbon group having 1 to 15 carbon atoms.

[0769] L x6 and L x7 each independently represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 14 carbon atoms. However, L x5 , L x6 and L x7 The total number of carbon atoms is 15 or less.

[0770] In formula (L1-4), L x8 and L x9 represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 12 carbon atoms.

[0771] W x1 represents a divalent alicyclic saturated hydrocarbon group having 3 to 15 carbon atoms. However, L x8 , L x9 and W x1 The total number of carbon atoms is 15 or less. L x1 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group.

[0772] L x2 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a single bond. L x3 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms.

[0773] L x4 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x5 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group.

[0774] L x6 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group. L x7 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms.

[0775] L x8is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a single bond or a methylene group. L x9 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a single bond or a methylene group.

[0776] W x1 is preferably a divalent alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms, more preferably a cyclohexanediyl group or an adamantanediyl group. Examples of the group represented by formula (L1-1) include the divalent groups shown below.

[0777] [ka]

[0778] Examples of the group represented by formula (L1-2) include the divalent groups shown below.

[0779] [ka]

[0780] Examples of the group represented by formula (L1-3) include the divalent groups shown below.

[0781] [ka]

[0782] Examples of the group represented by formula (L1-4) include the divalent groups shown below.

[0783] [ka]

[0784] L 55 is preferably a single bond or a group represented by formula (L1-1). The structural unit (a5-1) includes the structural units shown below and R in the structural unit (a5-1) in the structural units shown below. 51 The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example.

[0785] [ka]

[0786] When the resin (A) contains the structural unit (a5), the content thereof is preferably 1 to 30 mol %, more preferably 2 to 20 mol %, and even more preferably 3 to 15 mol %, based on all structural units in the resin (A).

[0787] <Structural unit (a6)> The structural unit (a6) is a structural unit having an -SO2- group, and preferably has an -SO2- group in a side chain.

[0788] The structural unit having an -SO2- group may have a linear structure having an -SO2- group, a branched structure having an -SO2- group, or a cyclic structure (monocyclic or polycyclic structure) having an -SO2- group. A structural unit having a cyclic structure having an -SO2- group is preferred, and a structural unit having a cyclic structure containing an -SO2-O- group (sultone ring) is more preferred.

[0789] The sultone ring may be a ring having the following formula (T 1 -1), formula (T 1 -2), formula (T 1 -3) and the formula (T 1 The bonding site can be any position. The sultone ring may be monocyclic, but is preferably polycyclic. A polycyclic sultone ring refers to a bridged ring containing -SO2-O- as an atomic group constituting the ring, and is represented by the formula (T 1 -1) and the formula (T 1 The sultone ring is represented by the formula (T 1As in the ring represented by formula (2), the atomic group constituting the ring may further contain a heteroatom in addition to —SO—O—. Examples of the heteroatom include an oxygen atom, a sulfur atom, and a nitrogen atom, and an oxygen atom is preferred.

[0790] [ka]

[0791] The sultone ring may have a substituent, and examples of the substituent include an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group, a halogen atom, a hydroxy group, a cyano group, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidyloxy group, an alkoxycarbonyl group having 2 to 12 carbon atoms, and an alkylcarbonyl group having 2 to 4 carbon atoms.

[0792] Halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, an octyl group, and a decyl group, and preferably an alkyl group having 1 to 6 carbon atoms, and more preferably a methyl group.

[0793] Examples of the alkyl group having a halogen atom include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group, a perfluorohexyl group, a trichloromethyl group, a tribromomethyl group, and a triiodomethyl group, and preferably a trifluoromethyl group.

[0794] Examples of the alkyl group having a hydroxy group include a hydroxymethyl group and a 2-hydroxyethyl group. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a decyloxy group, and a dodecyloxy group.

[0795] Examples of the aryl group include a phenyl group, a naphthyl group, an anthryl group, a p-methylphenyl group, a p-tert-butylphenyl group, a p-adamantylphenyl group, a tolyl group, a xylyl group, a cumyl group, a mesityl group, a biphenyl group, a phenanthryl group, a 2,6-diethylphenyl group, and a 2-methyl-6-ethylphenyl group.

[0796] Aralkyl groups include benzyl, phenethyl, phenylpropyl, naphthylmethyl, and naphthylethyl groups. Examples of the alkoxycarbonyl group include groups in which an alkoxy group, such as a methoxycarbonyl group or an ethoxycarbonyl group, is bonded to a carbonyl group, and preferably includes an alkoxycarbonyl group having 6 or less carbon atoms, more preferably a methoxycarbonyl group.

[0797] Alkylcarbonyl groups include acetyl, propionyl and butyryl groups. From the viewpoint of ease of production of the monomer from which the structural unit (a6) is derived, a sultone ring having no substituent is preferred.

[0798] The sultone ring is preferably a ring represented by the following formula (T1').

[0799] [ka]

[0800] [In formula (T1′), X 11 represents an oxygen atom, a sulfur atom or a methylene group.

[0801] R 41represents an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group, a halogen atom, a hydroxy group, a cyano group, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidyloxy group, an alkoxycarbonyl group having 2 to 12 carbon atoms, or an alkylcarbonyl group having 2 to 4 carbon atoms.

[0802] ma represents an integer of 0 to 9. When ma is 2 or more, multiple R 41 may be the same or different. The binding site is at any position.] X 11 is preferably an oxygen atom or a methylene group, more preferably a methylene group.

[0803] R 41 Examples of the substituent include the same as the substituent on the sultone ring, and an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group is preferred. ma is preferably 0 or 1, and more preferably 0.

[0804] Examples of the ring represented by formula (T1') include the following rings. The binding site may be any position. Among these, the binding site is preferably the 1st or 3rd position.

[0805] [ka]

[0806] The structural unit having an -SO2- group preferably further has a group derived from a polymerizable group, such as a vinyl group, an acryloyl group, a methacryloyl group, an acryloyloxy group, a methacryloyloxy group, an acryloylamino group, a methacryloylamino group, an acryloylthio group, or a methacryloylthio group.

[0807] Among these, the monomer from which the structural unit (a6) is derived is preferably a monomer having an ethylenically unsaturated bond, and more preferably a (meth)acrylic monomer. The structural unit (a6) is preferably a structural unit represented by the formula (a6-0).

[0808] [ka]

[0809] [In formula (a6-0), R x represents an alkyl group having 1 to 6 carbon atoms which may have one or more halogen atoms, a hydrogen atom, or a halogen atom.

[0810] A xx is an oxygen atom, -N(R c )- or a sulfur atom. A x represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the saturated hydrocarbon group is not -O-, -CO- or -N(R d )- may be replaced.

[0811] X 11 represents an oxygen atom, a sulfur atom or a methylene group. R 41 represents the same meaning as above. ma represents an integer of 0 to 9. When ma is 2 or more, multiple R 41 may be the same or different.

[0812] R c and R d each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R x Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0813] R x , R c and R dExamples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexyl group, and are preferably alkyl groups having 1 to 4 carbon atoms, and more preferably a methyl group or an ethyl group.

[0814] R x Examples of the alkyl group having a halogen atom include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group, a perfluorohexyl group, a trichloromethyl group, a tribromomethyl group, and a triiodomethyl group.

[0815] R x is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group. A x Examples of the divalent saturated hydrocarbon group include a linear alkanediyl group, a branched alkanediyl group, and a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, and may be a combination of two or more of these groups.

[0816] Specifically, methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group linear alkanediyl groups such as a dodecane-1,12-diyl group, a tridecane-1,13-diyl group, a tetradecane-1,14-diyl group, a pentadecane-1,15-diyl group, a hexadecane-1,16-diyl group, a heptadecane-1,17-diyl group, an ethane-1,1-diyl group, a propane-1,1-diyl group, and a propane-2,2-diyl group; branched alkanediyl groups such as butane-1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl; monocyclic divalent alicyclic saturated hydrocarbon groups such as cycloalkanediyl groups, such as cyclobutane-1,3-diyl, cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, and cyclooctane-1,5-diyl; Examples include polycyclic divalent alicyclic saturated hydrocarbon groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, and adamantane-2,6-diyl group.

[0817] A x The bonding position of to the sultone ring can be any position, but the 1-position is preferred. Examples of the structural unit (a6-0) include the following structural units.

[0818] [ka]

[0819] Of these, structural units represented by formula (a6-1), formula (a6-2), formula (a6-6), formula (a6-7), formula (a6-8), and formula (a6-12) are preferred, and structural units represented by formula (a6-1), formula (a6-2), formula (a6-7), and formula (a6-8) are more preferred.

[0820] When the resin (A) contains the structural unit (a6), the content thereof is preferably 1 to 50 mol %, more preferably 2 to 40 mol %, and even more preferably 3 to 30 mol %, based on all structural units in the resin (A).

[0821] <Structural unit (a7)> The resin (A) may further contain a structural unit that decomposes upon exposure to generate an acid (hereinafter, sometimes referred to as "structural unit (a7)"). Specific examples of the structural unit (a7) include the structural units described in JP 2016-79235 A, and are preferably structural units having a sulfonate group or carboxylate group and an organic cation in the side chain, or a structural unit having a sulfonio group and an organic anion in the side chain.

[0822] The structural unit having a sulfonate group or carboxylate group and an organic cation on the side chain is preferably a structural unit represented by formula (a7-A).

[0823] [ka]

[0824] [In formula (a7-A), R a7 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom.

[0825] X a71 represents a single bond, *-O-**, *-CO-O-**, *-O-CO-O-**, *-CO-NR a71 -**, *-NR a71 -CO-O-**, *-O-CO-NR a71 Represents -** or *-Ax-Ph-Ay-**.

[0826] R a71 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ph represents a phenylene group which may have a substituent. Ax and Ay each independently represent one or more bond types selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, an amide bond, and a carbonate ester bond.

[0827] * and ** represent binding sites, * represents R a7 represents the bonding site with the carbon atom to which it is attached. L a71 and L a72 each independently represents a hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-.

[0828] X a72 represents ***-CO-O-, ***-O-CO-, ***-O-CO-O-, ***-O-, and *** represents L a71 represents the binding site with na7 represents an integer of 0 to 2. When na7 is 2, the groups in the parentheses may be the same or different.

[0829] RA - represents a sulfonate anion or a carboxylate anion. ZA + represents an organic cation. R a7 and R a71 Examples of the alkyl group having 1 to 6 carbon atoms in the formula include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group.

[0830] R a7 Examples of the halogen atom in the formula include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R a7 Examples of the alkyl group having 1 to 6 carbon atoms and having a halogen atom in the formula (I) include a trifluoromethyl group, a difluoromethyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-octafluorobutyl group, a perfluoropentyl group, a 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, a perfluorohexyl group, a trichloromethyl group, a dichloromethyl group, a triiodomethyl group, a diiodomethyl group, a tribromomethyl group, and a dibromomethyl group.

[0831] R a7 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, further preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group.

[0832] X a71 is a group represented by *-Ax-Ph-Ay-**, it is preferably a linking group represented by the following formula (X10).

[0833] [ka]

[0834] [In formula (X10), Ax is R a7 represents a bond type that bonds to the carbon atom to which is bonded, and represents one or more bond types selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, a carbonate ester bond, and an amide bond.

[0835] Ay is L a71 and represents one or more bond species selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, a carbonate ester bond, and an amide bond.

[0836] Rx represents a halogen atom, a hydroxy group, a fluorinated alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. mx represents an integer of 0 to 4, and when mx is an integer of 2 or greater, multiple Rx's may be the same or different. When either Ax or Ay is a single bond, the other is preferably one or more bonds selected from the group consisting of an ether bond, a thioether bond, an ester bond, a carbonate ester bond, and an amide bond.

[0837] When either Ax or Ay is an amide bond, -CO-NR a71 A bond represented by - is preferred. The bonding position of Ay in the phenylene group is preferably the m-position or p-position relative to the bonding position of Ax, and more preferably the p-position.

[0838] Among these, Rx is preferably a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, or an ethyl group. mx is preferably 0, 1 or 2.

[0839] X a71 Examples of the group include a single bond and a group represented by the following formula (X 10 -1)~Formula(X 10 -10) is a group represented by *. a7 represents the bonding site with the carbon atom to which L is bonded. a71 X represents the binding site. 20 is -O- or -NR a71 - represents.

[0840] [ka]

[0841] Expression(X 10 -1)~Formula(X 10 Specific examples of the group represented by -10) include the following groups:

[0842] [ka]

[0843] Among them, X a71 is a single bond and a group of formula (X 10 -1′), formula (X 10 -3′)~Formula(X 10 -10′), and is preferably a single bond or a group represented by the formula (X 10 -1′), formula (X 10 -4′), formula (X 10 -5′), formula (X10 -6′) and formula (X 10 -10'), a single bond, a group represented by the formula (X 10 -1), a group represented by the formula (X 10 -5') or a group represented by the formula (X 10 It is more preferable that the group is a group represented by the formula (6').

[0844] L a71 The hydrocarbon group may be a group formed by removing one hydrogen atom from a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a group combining two or more of these groups to form X. a71 and X a72 In addition, L a72 The hydrocarbon group may be a group formed by removing one hydrogen atom from a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or a group combining two or more of these groups to form X. a72 and R.A. - Examples of such groups include groups that bond to the following:

[0845] L a71 and L a72 Examples of the chain hydrocarbon group include groups in which one hydrogen atom has been removed from an alkyl group or an alkenyl group. The alkyl group may be linear or branched, and specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decanyl, undecanyl, dodecanyl, tridecanyl, tetradecanyl, pentane decanyl, and heptadecanyl. Examples of the alkenyl group include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl.

[0846] The chain hydrocarbon group preferably has 1 to 20 carbon atoms, more preferably 1 to 18 carbon atoms, and even more preferably 1 to 10 carbon atoms. L a71and L a72 Examples of the alicyclic hydrocarbon group include groups in which one hydrogen atom has been removed from a monocyclic or polycyclic cycloalkyl group. Examples of the monocyclic cycloalkyl group include a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0847] L a71 and L a72 Examples of the polycyclic cycloalkyl group include a cycloalkyl group having a bridged structure, a cycloalkyl group in which two or more rings are fused, or a cycloalkyl group in which two rings are bonded via a spiro bond. Examples of the cycloalkyl group having a bridged structure include a norbornyl group and an adamantyl group. Examples of the cycloalkyl group in which two or more rings are fused include a bicyclo[4,4,0]decane group and a steroid group (steroid skeleton). Examples of the cycloalkyl group in which two rings are bonded via a spiro bond include a spirocyclic cycloalkyl group in which one cycloalkyl group selected from the group consisting of a cyclopentyl group, a cyclohexyl group, a norbornyl group, and an adamantyl group is bonded via a spiro bond to a cycloalkyl group having 5 to 8 carbon atoms. A double bond may be formed between two carbon atoms contained in the alicyclic hydrocarbon group. More specifically, examples of the alicyclic hydrocarbon group include alicyclic hydrocarbon groups represented by the following formula:

[0848] [ka]

[0849] When the alicyclic hydrocarbon group is a monocyclic cycloalkyl group, the alicyclic hydrocarbon group preferably has 3 to 18 carbon atoms, more preferably 3 to 12 carbon atoms, and even more preferably 3 to 8 carbon atoms. When the alicyclic hydrocarbon group is a polycyclic cycloalkyl group, the alicyclic hydrocarbon group preferably has 6 to 18 carbon atoms, and more preferably 7 to 12 carbon atoms.

[0850] L a71 and L a72Examples of the aromatic hydrocarbon group include groups in which one hydrogen atom has been removed from an aryl group. Examples of the aryl group include a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, and a fluorenyl group. The number of carbon atoms in the aromatic hydrocarbon group is preferably 5 to 14, more preferably 6 to 14, and even more preferably 6 to 10.

[0851] L a71 and L a72 When -CH2- in the hydrocarbon group is replaced with -O-, -CO-, -S- or -SO2-, the number of carbon atoms before replacement is regarded as the number of carbon atoms in the hydrocarbon group.

[0852] L a71 and L a72Among these hydrocarbon groups, groups in which -CH2- in a chain hydrocarbon group is replaced by -O-, -CO-, -S- or -SO2- include a hydroxy group (a group in which -CH2- in a methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- in an ethyl group is replaced by -O-CO-), a thiol group (a group in which -CH2- in a methyl group is replaced by -S-), a carbonyl group (a group in which -CH2- in a methylene group is replaced by -O-), a methyl group (a group in which -CH2- in a methyl group is replaced by -O-CO-), a methyl group (a group in which -CH2- in a methylene group is replaced by -O-CO-), a methyl group (a group in which -CH2- in a methyl ... a group in which -CH2- in a methylene group is replaced with -CO-), an oxy group (a group in which -CH2- in a methylene group is replaced with -O-), a thio group (a group in which -CH2- in a methylene group is replaced with -S-), a sulfonyl group (a group in which -CH2- in a methylene group is replaced with -SO2-), an alkoxy group (a group in which -CH2- at any position in an alkyl group is replaced with -O-), an alkoxycarbonyl group (an alkyl group in which...

Claims

1. An acid generator containing a salt represented by formula (I): 【Chemistry 1】 [In formula (I), Q １ , Q ２ , R １１ and R １２ each independently represents a hydrogen atom, a fluorine atom, an alkyl group having 1 to 6 carbon atoms, or a perfluoroalkyl group having 1 to 6 carbon atoms. z represents an integer of 0 to 6, and when z is 2 or more, the groups in the parentheses may be the same or different. X １Ａ is -O-, -CO-, -S-, -SO-, -SO ２ -, -NR ７ - or a group combining these. mm1 represents 0 or 1. L １０ represents a single bond or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and —CH ２ - is -O-, -S-, -SO ２ -, -SO-, -NR ７ It may be replaced by - or -CO-. R ７ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. L １Ａ , L １Ｂ , L ２ and L ３ each independently represents a single bond or an alkanediyl group having 1 to 6 carbon atoms which may have a substituent. R ５Ａ and R ５Ｂ are each independently -X １ -R １０ or -X ２ -L １１ -X １ -R １０ Represents. X １ is *-CO-O-, *-O-CO-, *-O-CO-O- or *-O- (where * is L １Ａ Or Ar １ Binding site with L １Ｂ Or Ar ２ or L １１ represents the binding site with. X ２ is *-CO-O-, *-O-CO-, *-O-CO-O- or *-O- (where * is L １Ａ Or Ar １ or L １Ｂ Or Ar ２ represents the binding site with. L １１ represents a hydrocarbon group having 1 to 28 carbon atoms which may have a substituent, and —CH ２ - is -O-, -S-, -SO ２ -, -SO-, -NR ７ It may be replaced by - or -CO-. R １０ represents an alicyclic hydrocarbon group having 3 to 36 carbon atoms and having one or more substituents, at least one of which is —OR １１ or a -I group. R １１ represents a hydrogen atom or an acid labile group. X ３ is -O-, -CO-, -S-, -SO-, -SO ２ -, -NR ７ - or a group combining these. Ar １ and Ar ２ each independently represents an aromatic hydrocarbon group having 6 to 18 carbon atoms. R ３ represents a fluorine atom, a fluoroalkyl group having 1 to 6 carbon atoms, an iodine atom, or a hydrocarbon group having 1 to 18 carbon atoms, and the hydrocarbon group may have a substituent. ２ - is -O-, -CO-, -S-, -SO-, -NR ７ -or-SO ２ It may be replaced with -. R ６ represents a fluorine atom, a fluorinated alkyl group having 1 to 6 carbon atoms, or a hydrocarbon group having 1 to 18 carbon atoms, and the hydrocarbon group may have a substituent. ２ - is -O-, -CO-, -S-, -SO-, -NR ７ -or-SO ２ It may be replaced with -. m2 represents an integer of 0 to 6, and when m2 is 2 or greater, the groups in the parentheses may be the same or different. 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, and when m2 is 0, R ３ At least one of R represents a fluorine atom or a fluorinated alkyl group having 1 to 6 carbon atoms, or R ３ is an iodine atom, and Ar １ -L binds to １Ａ -R ５Ａ or L １０ is bonded through a methylene group. m4 and m5 each independently represent an integer of 0 to 5, and when m4 is 2 or greater, the groups in the multiple parentheses may be the same as or different from each other, and when m5 is 2 or greater, the groups in the multiple parentheses may be the same as or different from each other. m6 represents an integer of 0 to 5, and when m6 is 2 or more, a plurality of R ６ may be the same or different from each other. However, 1≦(m2+m4)≦8, 1≦(m3+m6)≦10, and 1≦(m4+m5)≦10. Z ＋ represents an organic cation.

2. L １Ａ , L １Ｂ , L ２ and L ３ and each independently represent a single bond or an alkanediyl group having 1 to 4 carbon atoms which may have one or more halogen atoms.

3. m3 is an integer of 1 or more, and at least one R ３ 2. The acid generator according to claim 1, wherein is a fluorine atom, an iodine atom, a hydroxy group, a carboxy group, a hydroxyalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a perfluoroalkyl group having 1 to 3 carbon atoms.

4. m6 is an integer of 1 or more, and at least one R ６ 2. The acid generator according to claim 1, wherein is a fluorine atom, a hydroxy group, a carboxy group, a hydroxyalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a perfluoroalkyl group having 1 to 3 carbon atoms.

5. 2. The acid generator according to claim 1, wherein (m2+m4) is 1 or 2.

6. Ar １ and Ar ２ and each independently represent an aromatic hydrocarbon group having 6 to 14 carbon atoms.

7. L １０ is a single bond, a chain hydrocarbon group of 1 to 10 carbon atoms which may have a substituent, a cyclic hydrocarbon group of 3 to 24 carbon atoms which may have a substituent, or a group formed by combining a chain hydrocarbon group of 1 to 8 carbon atoms which may have a substituent and a cyclic hydrocarbon group of 3 to 24 carbon atoms which may have a substituent, The —CH contained in the chain hydrocarbon group and the cyclic hydrocarbon group ２ - is -O-, -S-, -SO ２ 2. The acid generator according to claim 1, wherein the aryl group may be substituted with - or -CO-.

8. R １０ is an alicyclic hydrocarbon group having 3 to 12 carbon atoms and having one or more substituents, At least one of the substituents is —OR １１ and R １１ is a hydrogen atom or an acid labile group, 2. The acid generator according to claim 1, wherein the acid labile group is a group represented by formula (1a) or a group represented by formula (2a). 【Chemistry 2】 [In formula (1a), R ａａ１ , R ａａ２ and R ａａ３ each independently represents 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 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these, or R ａａ１ and R ａａ２ are bonded to each other to form, together with the carbon atoms to which they are bonded, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, and the alkyl group, the alkenyl group, the alicyclic hydrocarbon group and the aromatic hydrocarbon group may have a halogen atom. naa represents 0 or 1. * indicates a binding site.] 【Transformation 3】 [In formula (2a), R ａａ１′ and R ａａ２′ each independently represents 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 and bonded to -C-X ａ Together with —, it forms a heterocyclic group having 3 to 20 carbon atoms, and —CH contained in the hydrocarbon group and the heterocyclic group ２ - may be replaced by -O- or -S-, and the hydrocarbon group and the heterocyclic group may have a halogen atom. X ａ represents an oxygen atom or a sulfur atom. * indicates a binding site.]

9. R １０ is an alicyclic hydrocarbon group having 3 to 12 carbon atoms and having one or more substituents, 2. The acid generator according to claim 1, wherein at least one of the substituents is a -I group.

10. A resist composition comprising the acid generator according to any one of claims 1 to 9.

11. Further, the composition contains a resin containing a structural unit having an acid labile group, The resist composition according to claim 10, wherein the structural unit having an acid labile group comprises at least one selected from the group consisting of a structural unit represented by formula (a1-0), a structural unit represented by formula (a1-1), a structural unit represented by formula (a1-2), a structural unit represented by formula (a1-4), a structural unit represented by formula (a1-5), and a structural unit represented by formula (a1-6). 【Chemistry 4】 [In formula (a1-0), formula (a1-1) and formula (a1-2), L ａ０１ , L ａ１ and L ａ２ are each independently —O— or *—O—(CH ２ ) ｋ１ represents —CO—O—, k1 represents an integer of 1 to 7, and * represents the bonding site with —CO—. R ａ０１ , R ａ４ and R ａ５ each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R ａ０２ , R ａ０３ and R ａ０４ each independently represents an alkyl group having 1 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 formed by combining these, and the alkyl group, alicyclic hydrocarbon group, and aromatic hydrocarbon group may contain a halogen atom. R ａ６ and R ａ７ each independently represents 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 formed by combining these, and the alkyl group, alkenyl group, alicyclic hydrocarbon group, and aromatic hydrocarbon group may contain a halogen atom. m1' represents an integer of 0 to 14. n1 represents an integer of 0 to 10. n1' represents an integer of 0 to 3. 【Transformation 5】 [In formula (a1-4), R ａ１ represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R ａ１７ represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, 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 ａ１１ represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and —CH ２ - represents -O-, -CO- or -NR ａ１８ May be replaced with -. R ａ１８ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X ａ１ represents a single bond or a carbonyl group. R ａ３４ and R ａ３５ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; R ａ３６ represents a hydrocarbon group having 1 to 20 carbon atoms, or R ａ３５ and R ａ３６ are bonded to each other to form a divalent hydrocarbon group having 2 to 20 carbon atoms together with the —C—O— to which they are bonded, and the hydrocarbon group and —CH contained in the divalent hydrocarbon group ２ - may be replaced by -O- or -S-. na1 represents an integer of 1 to 5, and when na1 is 2 or more, the groups in the parentheses may be the same or different. na11 represents an integer of 0 to 4, and when na11 is 2 or more, a plurality of R ａ１７ may be the same or different from each other. mc represents an integer of 0 to 2. 【Transformation 6】 [In formula (a1-5), R ａ８ represents an alkyl group having 1 to 6 carbon atoms which may have one or more halogen atoms, a hydrogen atom, or a halogen atom. Z ａ１ is a single bond or *-(CH ２ ) ｈ３ -CO-L ５４ -, h3 represents an integer of 1 to 4, * represents L ５１ represents the binding site with L ５１ , L ５２ , L ５３ and L ５４ each independently represents —O— or —S—. s1 represents an integer of 1 to 3. s1′ represents an integer of 0 to 3.] 【Transformation 7】 [In formula (a1-6), R ａ６１ represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R ａ６２ , R ａ６３ and R ａ６４ each independently represents an alkyl group having 1 to 6 carbon atoms or a cyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent, or R ａ６２ and R ａ６３ are bonded to each other to form a ring having 3 to 20 carbon atoms together with the carbon atoms to which they are attached. X ａ６１ represents a single bond, —CO—O—*, or —CO—NR ａ６５ - represents *, * represents the bonding site with Ar, R ａ６５ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X ａ６２ is a single bond, *-O-L ａ６１ - or *-CO-O-L ａ６２ -, * represents a bonding site with Ar, L ａ６１ and L ａ６２ each independently represents an alkanediyl group having 1 to 4 carbon atoms. Ar represents an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent.]

12. The resist composition according to claim 10, further comprising a resin containing a structural unit represented by formula (a2-A). 【Transformation 8】 [In formula (a2-A), R ａ２ represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R ａ２７ represents a halogen atom, a hydroxy group, a carboxy group, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, 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 ａ２１ represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and —CH ２ - represents -O-, -CO- or -NR ａ２８ May be replaced with -. R ａ２８ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X ａ２ represents a single bond or a carbonyl group. nA2 represents an integer of 1 to 5, and when nA2 is 2 or more, the groups in the parentheses may be the same or different. na21 represents an integer of 0 to 4, and when na21 is 2 or more, a plurality of R ａ２７ may be the same or different from each other. mc represents an integer of 0 to 2.

13. 11. The resist composition according to claim 10, further comprising a salt that generates an acid that is weaker in acidity than the acid generated from the acid generator.

14. (1) a step of applying the resist composition according to claim 10 onto a substrate; (2) drying the applied resist composition to form a composition layer; (3) exposing the composition layer to light; (4) a step of heating the composition layer after exposure; and (5) developing the composition layer after heating; A method for producing a resist pattern comprising the steps of:

15. A salt represented by formula (I): 【Chemistry 9】 [In formula (I), Q １ , Q ２ , R １１ and R １２ each independently represents a hydrogen atom, a fluorine atom, an alkyl group having 1 to 6 carbon atoms, or a perfluoroalkyl group having 1 to 6 carbon atoms. z represents an integer of 0 to 6, and when z is 2 or more, the groups in the parentheses may be the same or different. X １Ａ is -O-, -CO-, -S-, -SO-, -SO ２ -, -NR ７ - or a group combining these. mm1 represents 0 or 1. L １０ represents a single bond or a hydrocarbon group having 1 to 40 carbon atoms which may have a substituent, and —CH ２ - is -O-, -S-, -SO ２ -, -SO-, -NR ７ It may be replaced by - or -CO-. R ７ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. L １Ａ , L １Ｂ , L ２ and L ３ each independently represents a single bond or an alkanediyl group having 1 to 6 carbon atoms which may have a substituent. R ５Ａ and R ５Ｂ are each independently -X １ -R １０ or -X ２ -L １１ -X １ -R １０ Represents. X １ is *-CO-O-, *-O-CO-, *-O-CO-O- or *-O- (where * is L １Ａ Or Ar １ Binding site with L １Ｂ Or Ar ２ or L １１ represents the binding site with. X ２ is *-CO-O-, *-O-CO-, *-O-CO-O- or *-O- (where * is L １Ａ Or Ar １ or L １Ｂ Or Ar ２ represents the binding site with. L １１ represents a hydrocarbon group having 1 to 28 carbon atoms which may have a substituent, and —CH ２ - is -O-, -S-, -SO ２ -, -SO-, -NR ７ It may be replaced by - or -CO-. R １０ represents an alicyclic hydrocarbon group having 3 to 36 carbon atoms and having one or more substituents, at least one of which is —OR １１ or a -I group. R １１ represents a hydrogen atom or an acid labile group. X ３ is -O-, -CO-, -S-, -SO-, -SO ２ -, -NR ７ - or a group combining these. Ar １ and Ar ２ each independently represents an aromatic hydrocarbon group having 6 to 18 carbon atoms. R ３ represents a fluorine atom, a fluoroalkyl group having 1 to 6 carbon atoms, an iodine atom, or a hydrocarbon group having 1 to 18 carbon atoms, and the hydrocarbon group may have a substituent. ２ - is -O-, -CO-, -S-, -SO-, -NR ７ -or-SO ２ It may be replaced with -. R ６ represents a fluorine atom, a fluorinated alkyl group having 1 to 6 carbon atoms, or a hydrocarbon group having 1 to 18 carbon atoms, and the hydrocarbon group may have a substituent. ２ - is -O-, -CO-, -S-, -SO-, -NR ７ -or-SO ２ It may be replaced with -. m2 represents an integer of 0 to 6, and when m2 is 2 or greater, the groups in the parentheses may be the same or different. 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, and when m2 is 0, R ３ At least one of R represents a fluorine atom or a fluorinated alkyl group having 1 to 6 carbon atoms, or R ３ is an iodine atom, and Ar １ -L binds to １Ａ -R ５Ａ or L １０ is bonded through a methylene group. m4 and m5 each independently represent an integer of 0 to 5, and when m4 is 2 or greater, the groups in the multiple parentheses may be the same as or different from each other, and when m5 is 2 or greater, the groups in the multiple parentheses may be the same as or different from each other. m6 represents an integer of 0 to 5, and when m6 is 2 or more, a plurality of R ６ may be the same or different from each other. However, 1≦(m2+m4)≦8, 1≦(m3+m6)≦10, and 1≦(m4+m5)≦10. Z ＋ represents an organic cation.

16. L １Ａ , L １Ｂ , L ２ and L ３ and each independently represent a single bond or an alkanediyl group having 1 to 4 carbon atoms which may have one or more halogen atoms.

17. m3 is an integer of 1 or more, and at least one R ３ is a fluorine atom, an iodine atom, a hydroxy group, a carboxy group, a hydroxyalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a perfluoroalkyl group having 1 to 3 carbon atoms.

18. m6 is an integer of 1 or more, and at least one R ６ The salt according to claim 15 or 16, wherein is a fluorine atom, a hydroxy group, a carboxy group, a hydroxyalkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or a perfluoroalkyl group having 1 to 3 carbon atoms.

19. The salt according to claim 15 or 16, wherein (m2+m4) is 1 or 2.

20. Ar １ and Ar ２ and each independently represent an aromatic hydrocarbon group having 6 to 14 carbon atoms.

21. L １０ is a single bond, a chain hydrocarbon group of 1 to 10 carbon atoms which may have a substituent, a cyclic hydrocarbon group of 3 to 24 carbon atoms which may have a substituent, or a group formed by combining a chain hydrocarbon group of 1 to 8 carbon atoms which may have a substituent and a cyclic hydrocarbon group of 3 to 24 carbon atoms which may have a substituent, The —CH contained in the chain hydrocarbon group and the cyclic hydrocarbon group ２ - is -O-, -S-, -SO ２ The salt according to claim 15 or 16, which may be substituted with - or -CO-.

22. R １０ is an alicyclic hydrocarbon group having 3 to 12 carbon atoms and having one or more substituents, At least one of the substituents is —OR １１ and R １１ is a hydrogen atom or an acid labile group, 17. The salt according to claim 15 or 16, wherein the acid labile group is a group represented by formula (1a) or a group represented by formula (2a). 【Chemistry 10】 [In formula (1a), R ａａ１ , R ａａ２ and R ａａ３ each independently represents 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 20 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these, or R ａａ１ and R ａａ２ are bonded to each other to form, together with the carbon atoms to which they are bonded, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, and the alkyl group, the alkenyl group, the alicyclic hydrocarbon group and the aromatic hydrocarbon group may have a halogen atom. naa represents 0 or 1. * indicates a binding site.] 【Chemistry 11】 [In formula (2a), R ａａ１′ and R ａａ２′ each independently represents 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 and bonded to -C-X ａ Together with —, it forms a heterocyclic group having 3 to 20 carbon atoms, and —CH contained in the hydrocarbon group and the heterocyclic group ２ - may be replaced by -O- or -S-, and the hydrocarbon group and the heterocyclic group may have a halogen atom. X ａ represents an oxygen atom or a sulfur atom. * indicates a binding site.]

23. R １０ is an alicyclic hydrocarbon group having 3 to 12 carbon atoms and having one or more substituents, The salt according to claim 15 or 16, wherein at least one of the substituents is a -I group.

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