Carboxylate, carboxylic acid generator, resist composition, and method for producing resist pattern

Abstract

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

Description

[Technical Field]

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

[0002] Patent Document 1 describes a resist composition that contains a carboxylic acid salt represented by the following formula as a carboxylic acid generator.

[0003] [ka]

[0004] Patent Document 2 describes a resist composition that contains a salt represented by the following formula as an acid generator.

[0005] [ka] [Prior art documents] [Patent documents]

[0006] [Patent Document 1] Japanese Patent Application Laid-Open No. 2011-039502 [Patent Document 2] Japanese Patent Application Laid-Open No. 2011-085878 Summary of the Invention [Problem to be solved by the invention]

[0007] There is a need for a technology that can produce resist patterns with good CD uniformity (CDU). [Means for solving the problem]

[0008] The present invention includes the following inventions. [Invention 1] A carboxylic acid generator containing a carboxylic acid salt represented by formula (I):

[0009] [ka]

[0010] [In formula (I), X represents a sulfur atom or an iodine atom. m10 represents 0 or 1, and when X is a sulfur atom, m10 is 1, and when X is an iodine atom, m10 is 0.

[0011] R 1A and R 1B are each independently *-X 1 -R 10 or *-X 1 -L 10 -X 2 -R 10 * represents R 4 is bonded to the benzene ring or R 7 represents the bonding site with the benzene ring to which it is attached.

[0012] X 1 and X 2 are each independently *-CO-O-, *-O-CO-, *-O-CO-O- or *-O- (where * represents a benzene ring or L 10 represents the binding site with L 10 represents a hydrocarbon group having 1 to 28 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -SO2- or -CO-.

[0013] R 10 represents a group having -SO2-. R 4 represents a halogen atom or a hydrocarbon group having 1 to 36 carbon atoms, the hydrocarbon group optionally having a substituent, and -CH2- contained in the hydrocarbon group optionally being replaced by -O-, -S-, -CO-, -SO- or -SO2-.

[0014] R 7, R 8 and R 9 each independently represents a halogen atom or a hydrocarbon group having 1 to 36 carbon atoms, and the hydrocarbon group may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO-, -SO- or -SO2-. When X is a sulfur atom, R 7 and R 8 or R 8 and R 9 are combined to form S + The R forming the ring may form a ring containing 7 and R 8 or R 8 and R 9 is S + and a single bond formed between two benzene rings. The —CH— contained in the ring may be replaced by —O—, —S—, —CO—, —SO—, or —SO—.

[0015] m1A represents an integer of 0 to 5, and when m1A is 2 or more, a plurality of R 1A may be the same or different from each other. m1B represents an integer of 0 to 4, and when m1B is 2 or more, a plurality of R 1B may be the same or different, provided that either m1A or m1B is an integer of at least 1.

[0016] m4 represents an integer of 0 to 5, and when m4 is 2 or more, a plurality of R 4 may be the same or different, and satisfy the relationship 0≦m1A+m4≦5. m7 represents an integer of 0 to 4, and when m7 is 2 or more, a plurality of R 7 may be the same or different, and satisfy the relationship 0≦m1B+m7≦4.

[0017] m8 represents an integer of 0 to 5, and when m8 is 2 or more, a plurality of R 8 may be the same or different from each other. m9 represents an integer of 0 to 5, and when m9 is 2 or more, a plurality of R9 may be the same or different from each other.

[0018] X 0 represents a hydrocarbon group having 2 to 72 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-.] [Invention 2] R 10 The carboxylic acid generator according to [Invention 1], wherein the group having —SO 2 — is a group having a ring represented by formula (T1A).

[0019] [ka]

[0020] [In formula (T1A), X 1A represents an oxygen atom, a sulfur atom, —NH—, or a methylene group. R 41A represents 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.

[0021] ma represents an integer of 0 to 9. When ma is 2 or more, multiple R 41A may be the same or different. The binding site is at any position.] [Invention 3] m1A is an integer of 1 to 3, R 1A But, -O-CO-OR 10 or -OL 10 -CO-OR 10 The carboxylic acid generator according to [Invention 1] or [Invention 2],

[0022] [Invention 4] X0 represents an alicyclic hydrocarbon group having 3 to 36 carbon atoms, an aromatic hydrocarbon group having 6 to 36 carbon atoms, or a group comprising a combination of a chain hydrocarbon group having 1 to 18 carbon atoms and an alicyclic hydrocarbon group having 3 to 36 carbon atoms or an aromatic hydrocarbon group having 6 to 36 carbon atoms, The alicyclic hydrocarbon group, the chain hydrocarbon group, and the aromatic hydrocarbon group may have a fluorine atom, an iodine atom, a fluorinated alkyl group having 1 to 4 carbon atoms, or a hydroxy group, and -CH2- contained in the alicyclic hydrocarbon group and the chain hydrocarbon group may be replaced with -O-, -S-, -CO-, or -SO2-. The carboxylic acid generator according to any one of [Invention 1] to [Invention 3].

[0023] [Invention 5] X 0 is a group represented by formula (aa): The carboxylic acid generator according to any one of [Invention 1] to [Invention 4].

[0024] [ka]

[0025] [In formula (aa), X a and X b each independently represents -O- or -S-. X 1a 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-.

[0026] X 2a represents a hydrocarbon group having 1 to 48 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-.

[0027] * -COO - represents the bonding site with the carbon atom of [Invention 6] X 0is a phenyl group which may have a fluorine atom, an iodine atom, a fluorinated alkyl group having 1 to 4 carbon atoms or a hydroxy group.

[0028] [Invention 7] A resist composition comprising the carboxylic acid generator according to any one of [Invention 1] to [Invention 6] and an acid generator other than the carboxylic acid generator.

[0029] [Invention 8] further containing a resin containing a structural unit having an acid labile group, The resist composition according to [Invention 7], 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).

[0030] [ka]

[0031] [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—.

[0032] 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 a04each 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.

[0033] 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.

[0034] m1′ represents an integer of 0 to 14. n1 represents an integer of 0 to 10. n1′ represents an integer of 0 to 3.

[0035] [ka]

[0036] [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.

[0037] 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.

[0038] A a11represents 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

[0039] 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-.

[0040] 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 from each other. 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.

[0041] mc represents an integer between 0 and 2.

[0042] [ka]

[0043] [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.

[0044] Z a1 is a single bond or -(CH2) h3 -CO-L54 -, 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-.

[0045] s1 represents an integer of 1 to 3. s1′ represents an integer of 0 to 3.

[0046] [ka]

[0047] [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.

[0048] 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.

[0049] X a61 is a single bond, -CO-O-* or -CO-NR 5 -*, * represents the binding site with Ar, R 5 represents a hydrogen atom or an alkyl group having 1 to 4 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.

[0050] Ar represents an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent.] [Invention 9] The resist composition according to [Invention 7] or [Invention 8], further comprising a resin containing a structural unit represented by formula (a2-A).

[0051] [ka]

[0052] [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.

[0053] 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.

[0054] 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

[0055] 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. When nA2 is 2 or greater, the groups in the parentheses may be the same or different.

[0056] na21 represents an integer of 0 to 4. When na21 is 2 or more, a plurality of R a27may be the same or different from each other. mc represents an integer between 0 and 2. [Invention 10] The resist composition according to any one of [Invention 7] to [Invention 9], wherein the acid generator further comprises a salt represented by formula (B1).

[0057] [ka]

[0058] [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-.

[0059] 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-.

[0060] 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-.

[0061] 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. [Invention 11] (1) A step of applying the resist composition according to any one of [Invention 7] to [Invention 10] 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 heated composition layer; A method for producing a resist pattern comprising the steps of:

[0062] [Invention 12] A carboxylate represented by the above formula (I). [Invention 13] R 10 The carboxylate according to [Invention 12], wherein the group having —SO2— is a group having a ring represented by the above formula (T1A).

[0063] [Invention 14] m1A is an integer of 1 to 3, R 1A But, -O-CO-OR 10 or -OL 10 -CO-OR 10 The carboxylate according to [Invention 12] or [Invention 13],

[0064] [Invention 15] X 0 is an alicyclic hydrocarbon group having 3 to 36 carbon atoms, an aromatic hydrocarbon group having 6 to 36 carbon atoms, or a group formed by combining a chain hydrocarbon group having 1 to 18 carbon atoms with an alicyclic hydrocarbon group having 3 to 36 carbon atoms or an aromatic hydrocarbon group having 6 to 36 carbon atoms, The carboxylic acid salt according to any one of [Invention 12] to [Invention 14], wherein the alicyclic hydrocarbon group, the chain hydrocarbon group, and the aromatic hydrocarbon group may have a fluorine atom, an iodine atom, a fluorinated alkyl group having 1 to 4 carbon atoms, or a hydroxy group, and -CH2- contained in the alicyclic hydrocarbon group and the chain hydrocarbon group may be replaced by -O-, -S-, -CO-, or -SO2-.

[0065] [Invention 16] X 0 is a group represented by formula (aa): [Invention 12] to [Invention 15].

[0066] [ka]

[0067] [In formula (aa), X a and X b each independently represents -O- or -S-. X 1a 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-.

[0068] X 2a represents a hydrocarbon group having 1 to 48 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-.

[0069] * -COO - represents the bonding site with the carbon atom of [Invention 17] X 0 is a phenyl group which may have a fluorine atom, an iodine atom, a fluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group. [Effects of the Invention]

[0070] By using the resist composition of the present invention, a resist pattern with good CD uniformity (CDU) can be produced. DETAILED DESCRIPTION OF THE INVENTION

[0071] As used herein, "(meth)acrylic monomer" refers to "at least one of an acrylic monomer and a methacrylic monomer." The terms "(meth)acrylate" and "(meth)acrylic acid" have the same meaning. Regarding groups described herein, those that can have either a linear or branched structure are acceptable. When -CH2- in a hydrocarbon group or the like is replaced with -O-, -S-, -CO-, or -SO2-, the same applies to each group, and the number of carbon atoms before the replacement is the number of carbon atoms in the hydrocarbon group or the like. A "combined group" refers to a group formed by combining two or more of the exemplified groups, and the valence of these groups may vary depending on the bonding form. "Derived from" or "derived from" refers to a polymerizable C=C bond in the molecule that becomes a -CC- group (single bond) upon polymerization. When stereoisomers exist, all stereoisomers are included. Depending on the number of substituents, any position and number of hydrogen atoms in each group may be replaced by a bonding site. The number of carbon atoms in a substituent is not included in the number of carbon atoms in the substituted group. An acid labile group means a group that, when contacted with an acid (e.g., trifluoromethanesulfonic acid, etc.), eliminates a leaving group to form a hydrophilic group (e.g., a hydroxy group or a carboxy group, etc.). A base labile group means a group that, when contacted with a base (e.g., trimethylamine, etc.), eliminates a 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. [Carboxylate represented by formula (I)] The present invention relates to a carboxylate salt represented by formula (I) (hereinafter sometimes referred to as "salt (I)" or "carboxylate (I)").

[0073] In the salt (I), the side with a positive charge is sometimes called the "cation (I)" and the side with a negative charge is sometimes called the "anion (I)." [Cation (I)] The cation (I) of the salt represented by formula (I) is a cation represented by formula (IC).

[0074] [ka]

[0075] [In formula (IC), all symbols have the same meanings as in formula (I)] R 1A and R 1B X included in 1 is preferably *-CO-O-, *-O- or *-O-CO-O- (* represents the bonding site to the benzene ring), and more preferably *-O- or *-O-CO-O-.

[0076] R 1A and R 1B X included in 2 is *-CO-O-, *-O-CO- or *-O-CO-O- (* is L 10 It is preferably *-CO-O- or *-O-CO-.

[0077] R 1A and R 1B L included in 10 Examples of the hydrocarbon group in include chain hydrocarbon groups such as alkanediyl groups, monocyclic or polycyclic (including spiro ring) alicyclic hydrocarbon groups, and aromatic hydrocarbon groups, and may also be groups formed by combining two or more of these groups (for example, a hydrocarbon group formed from an alicyclic hydrocarbon group and an alkanediyl group).

[0078] 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.

[0079] The chain hydrocarbon group preferably has 1 to 18 carbon atoms, more preferably 1 to 12 carbon atoms, even more preferably 1 to 9 carbon atoms, even more preferably 1 to 6 carbon atoms, and even more preferably 1 to 4 carbon atoms.

[0080] Examples of the monocyclic or polycyclic alicyclic hydrocarbon group include the following groups: The binding site can be any position.

[0081] [ka]

[0082] 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 is preferably 3 to 18, more preferably 3 to 16, and even more preferably 3 to 12.

[0083] 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 preferably has 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms.

[0084] Examples of the group combining two or more groups include a group combining an alicyclic hydrocarbon group with an alkanediyl group, a group combining an aromatic hydrocarbon group with an alkanediyl group, and a group combining an alicyclic hydrocarbon group with 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 X 1 or X 2 may be bound to

[0085] Examples of groups combining an alicyclic hydrocarbon group and an alkanediyl group include -divalent alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-divalent alicyclic hydrocarbon group-alkanediyl group-, and -alkanediyl group-divalent alicyclic hydrocarbon group-.

[0086] Examples of groups combining an aromatic hydrocarbon group and an alkanediyl group include -divalent aromatic hydrocarbon group-alkanediyl group-, -alkanediyl group-divalent aromatic hydrocarbon group-alkanediyl group-, and -alkanediyl group-divalent aromatic hydrocarbon group-.

[0087] 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-.

[0088] L 10 The —CH2— contained in the hydrocarbon group having 1 to 28 carbon atoms may be replaced with —O—, —S—, —SO2— or —CO—. L 10 When a —CH2— contained in the 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 hydrocarbon group.

[0089] 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 oxy group (a group in which -CH2- in a methylene group is replaced by -O-), a carbonyl group (a group in which -CH2- in a methylene group is replaced by -CO-), a thio group (a group in which -CH2- in a methylene group is replaced by -CO-), a methyl group (a group in which -CH2- in a methylene group is replaced by -CO-), a methyl group (a group in which -CH2- in a methylene group is replaced by -O ... a group in which -CH2- in the alkyl 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 alkylthio group (a group in which -CH2- at any position in an alkyl group is replaced with -S-), an alkylsulfonyl group (a group in which -CH2- at any position in an alkyl group is replaced with -SO2-), an alkoxycarbonyl group (a group in which -CH2-CH2- at any position in an alkyl group is replaced with -O-C O-), 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-), alkanediyloxy group (a group in which -CH2- at any position in an alkanediyl group is replaced with -O-), alkanediyloxycarbonyl group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -O-CO-), alkanediylcarbonyl group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -O-CO-), 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 include an aromatic hydrocarbon group-carbonyloxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy group, and a group formed by combining two or more of these groups.

[0090] 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.

[0091] 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, a pentylthio group, a hexylthio group, an octylthio group, a 2-ethylhexylthio group, a nonylthio group, a decylthio group, an undecylthio 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.

[0092] 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.

[0093] 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, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, an octylsulfonyl group, a 2-ethylhexylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl 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.

[0094] 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.

[0095] 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.

[0096] 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.

[0097] Examples of the alkanediylthio group include alkanediylthio groups having 1 to 27 carbon atoms, such as a methylenethio group, an ethylenethio group, a propylenethio 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.

[0098] 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 27 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.

[0099] Examples of groups in which -CH2- in an alicyclic hydrocarbon group is replaced with -O-, -S-, -CO- or -SO2- include the following groups. -O- or -CO- in the groups shown below may be replaced with -S- or -SO2-, respectively. The bonding site may be at any position.

[0100] [ka]

[0101] L 10 Examples of the substituent that may be possessed by L include a halogen atom and a cyano group. 10In 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 used as a substituent of the alicyclic hydrocarbon group or the aromatic hydrocarbon group. 10 The -CH2- in the chain hydrocarbon group such as the alkyl group in the formula (I) is replaced with -O-, -CO-, -S- or -SO2-, thereby forming L 10 can substantially have a substituent such as a hydroxy group, a carboxy group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, a thiol group, an alkylthio group, or an alkylsulfonyl group.

[0102] 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.

[0103] L 10 is preferably an alkanediyl group having 1 to 10 carbon atoms (-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 (-CH2- contained in the alkanediyl group and the alicyclic hydrocarbon group may be replaced with -O- or -CO-), 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.

[0104] R 1A and R 1B R included in 10The group having -SO2- in the formula (I) may be a group having -SO2- in a linear structure, a group having -SO2- in a branched structure, or a group having -SO2- in a cyclic structure (monocyclic or polycyclic). A group having -SO2- in a cyclic structure (monocyclic or polycyclic) is preferred, and a group having a cyclic structure (sultone ring) containing -SO2-O- is more preferred.

[0105] Examples of the sultone ring include those represented by the following formula (T 1 Here, the bonding site of the sultone ring can be at any position (the same applies hereinafter).

[0106] [ka]

[0107] Formula(T 1 In the above, ring A represents a sultone ring having 2 to 24 carbon atoms. -CH2- contained in ring A may be replaced with -O-, -S- or -NH-. R 41A represents 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.

[0108] ma represents an integer of 0 to 9. When ma is 2 or more, multiple R 41A may be the same or different. The sultone ring may be either monocyclic or polycyclic.

[0109] The number of carbon atoms in the sultone ring is preferably 3 to 24, more preferably 3 to 20, even more preferably 3 to 18, still more preferably 3 to 16, even more preferably 3 to 12, and still more preferably 3 to 10.

[0110] The sultone ring of ring A is preferably a sultone ring having 3 to 18 carbon atoms, more preferably a sultone ring having 3 to 10 carbon atoms, and examples thereof include sultone rings represented by the following formula (T 1 -0), a polycyclic ring represented by the formula (T 1 -3) and the formula (T 1 Among them, a polycyclic ring is preferable. The polycyclic sultone ring means a bridged ring containing -SO2-O- as an atomic group constituting the ring, and is represented by the formula (T 1 -1), formula (T 1 -2), formula (T 1 -5) and formula (T 1 The sultone ring is represented by the formula (T 1 -2), formula (T 1 -5) and formula (T 1 As in the ring represented by formula (6), in addition to -SO2-O-, a hetero atom may be contained as a ring-constituting atom. Examples of the hetero atom include an oxygen atom, a sulfur atom, and a nitrogen atom, and an oxygen atom is preferred.

[0111] [ka]

[0112] where X 1A represents an oxygen atom, a sulfur atom, —NH—, or a methylene group. X 1A is preferably an oxygen atom or a methylene group, more preferably a methylene group.

[0113] R 41A Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. 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. Preferably, it is an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group or an ethyl group.

[0114] 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.

[0115] Examples of the alkyl group having a hydroxy group include a hydroxyalkyl group such as 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.

[0116] 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.

[0117] Examples of the aralkyl group include a benzyl group, a phenethyl group, a phenylpropyl group, a naphthylmethyl group, and a naphthylethyl group. 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.

[0118] Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, and a butyryl group. R 41Ais preferably an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group, a halogen atom or a hydroxy group, more preferably an alkyl group having 1 to 4 carbon atoms, even more preferably a methyl group or an ethyl group, and even more preferably a methyl group.

[0119] ma is preferably an integer of 0 to 7, more preferably an integer of 0 to 4, further preferably 0 or 1, and even more preferably 0. In other words, the group having -SO2- is more preferably a group having a sultone ring without a substituent.

[0120] As the sultone ring, a ring represented by the following formula (T1A) is preferred, and a ring represented by the formula (T1) is more preferred.

[0121] [ka]

[0122] [In formula (T1A) and formula (T1), all symbols have the same meanings as defined above.] Formula(T 1 ), the ring represented by formula (T1A), and the ring represented by formula (T1) include the following rings. As described above, the binding site can be at any position, but in the following rings, the 1st or 3rd position is preferred, and the 1st position is more preferred.

[0123] [ka]

[0124] m1A is preferably an integer of 0 to 4, more preferably an integer of 0 to 3, even more preferably an integer of 1 to 3, even more preferably 1 or 2, and even more preferably 1.

[0125] m1B 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.

[0126] R 1A The bonding position of to the benzene ring is X + The position of X may be ortho, meta or para relative to the position of the bond to the benzene ring. + It is preferable that at least one of the groups is bonded at the ortho-position or the para-position relative to the bonding position of the benzene ring to which the group is bonded.

[0127] R 1B The bonding position of to the benzene ring is X + The bonding position of X may be ortho, meta or para. + It is preferable that at least one of the bonds is at the ortho-position or meta-position relative to the bonding positions of the above.

[0128] R 1A and R 1B are each independently -OR 10 , -CO-OR 10 , -O-CO-R 10 , -O-CO-OR 10 or -OL 10 -CO-OR 10 is preferably —O—CO—R 10 , -O-CO-OR 10 or -OL 10 -CO-OR 10 More preferably, it is —O—CO—OR 10 or -OL 10 -CO-OR 10 More preferably, -OL 10 -CO-OR 10 It is even more preferred that:

[0129] R 4 , R 7 , R 8 and R 9Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R 4 , R 7 , R 8 and R 9 Examples of the hydrocarbon group having 1 to 36 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 30, more preferably 1 to 24, and even more preferably 1 to 18.

[0130] 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.

[0131] The alkanediyl group is a linear or branched alkanediyl group, such as a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, or a hexane-1,6-diyl group; and 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.

[0132] The chain hydrocarbon group preferably has 1 to 18 carbon atoms, more preferably 1 to 12 carbon atoms, even more preferably 1 to 9 carbon atoms, still more preferably 1 to 6 carbon atoms, even more preferably 1 to 4 carbon atoms, and still more preferably 1 to 3 carbon atoms.

[0133] 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.

[0134] [ka]

[0135] Specifically, examples of monocyclic alicyclic hydrocarbon groups include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and cyclododecyl. Examples of polycyclic alicyclic hydrocarbon groups include polycyclic cycloalkyl groups such as decahydronaphthyl, adamantyl, and norbornyl; cycloalkyl groups such as spirocyclohexane-1,2'-cyclopentane and spiroadamantane-2,3'-cyclopentane; and spiro rings 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 is preferably 3 to 18, more preferably 3 to 16, and even more preferably 3 to 12.

[0136] 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.

[0137] Examples of groups formed by combining two or more of chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups include a group combining an aromatic hydrocarbon group and a chain hydrocarbon group (for example, aromatic hydrocarbon group-alkanediyl group-*, alkyl group-aromatic hydrocarbon group-*, alkyl group-aromatic hydrocarbon group-alkanediyl group-*, where -CH2- contained in the alkanediyl group and the alkyl group may be replaced by -O-, -CO-, -S-, or -SO2-), a group combining an alicyclic hydrocarbon group and a chain hydrocarbon group (for example, alicyclic hydrocarbon group-alkanediyl group- Examples of such groups include an alkanediyl group-*, an alkyl group-alicyclic hydrocarbon group-*, an alkyl group-alicyclic hydrocarbon group-alkanediyl group-*, where —CH— contained in the alicyclic hydrocarbon group, the alkanediyl group, and the alkyl group may be replaced by —O—, —CO—, —S—, or —SO—, and groups combining an aromatic hydrocarbon group and an alicyclic hydrocarbon group (for example, an aromatic hydrocarbon group-alicyclic hydrocarbon group-*, an alicyclic hydrocarbon group-aromatic hydrocarbon group-*, where —CH— contained in the alicyclic hydrocarbon group may be replaced by —O—, —CO—, —S—, or —SO—). * represents a bonding site.

[0138] 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.

[0139] 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.

[0140] 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.

[0141] 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.

[0142] In the group formed by combining these groups, two or more types of alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may be combined, and any of these groups may be bonded to a benzene ring.

[0143] R 4 , R 7 , R 8 and R 9 When -CH2- in the hydrocarbon group represented by the formula (I) is replaced by -O-, -CO-, -S-, -SO-, or -SO2-, the number of carbon atoms before the replacement is counted as the total number of carbon atoms in the hydrocarbon group. The number of replacements may be one or more.

[0144] Examples of groups in which -CH2- in a hydrocarbon group is replaced by -O-, -CO-, -S-, -SO- or -SO2- include a hydroxy group (a group in which -CH2- in a methyl group is replaced by -O-), a thiol group (a group in which -CH2- in a methyl group is replaced by -S-), a carboxy group (a group in which -CH2-CH2- in an ethyl group is replaced by -O-CO-), 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- at any position in an alkyl group is replaced by -O-), and H2- is replaced by -O-CO-), alkylcarbonyl group (a group in which -CH2- at any position in the alkyl group is replaced by -CO-), alkylcarbonyloxy group (a group in which -CH2-CH2- at any position in the alkyl group is replaced by -CO-O-), alkylthio group (a group in which -CH2- at any position in the alkyl group is replaced by -S-), alkylsulfil group (a group in which -CH2- at any position in the alkyl group is replaced by -SO-), alkylsulfonyl group (a group in which -CH2- at any position in the alkyl group is replaced by -SO-), alkylsulfonyl group (a group in which -CH2- at any position in the alkyl group is replaced by -CO-), alkylcarbonyloxy group (a group in which -CH2-CH2- at any position in the alkyl group is replaced by -CO-O-), alkylthio group (a group in which -CH2- at any position in the alkyl group is replaced by -S-), alkylsulfonyl ...CO-), alkylsulfonyl group (a group in which -CH2- at any position in the alkyl group is replaced by -CO-), alkylsulfonyloxy group (a group in which -CH2- at any position in the alkyl group is replaced by -CO-), alkylsulfonyl in a methylene group is replaced with -SO2-), an oxy group (a group in which -CH2- in a methylene group is replaced with -O-), 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 sulfyl group (a group in which -CH2- in a methylene group is replaced with -SO-), 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 -SO2-), an alkanediyloxy group (a group in which -CH2- at any position in an alkanediyl group is replaced with -SO2-), an alkanediyloxy group (a group in which -CH2- in ... is replaced by -O-), an alkanediyloxycarbonyl group (a group in which -CH2-CH2- at any position contained in an alkanediyl group is replaced by -O-CO-), an alkanediylcarbonyl group (a group in which -CH2- at any position contained in an alkanediyl group is replaced by -CO-), an alkanediylcarbonyloxy group (a group in which -CH2-CH2- at any position contained in an alkanediyl group is replaced by -CO-O-), an alkanediylthio group (a group in which -CH2- at any position contained in an alkanediyl group is replaced by -S-),Examples of such groups include an alkanediylsulfyl group (a group in which -CH- at any position in an alkanediyl group is replaced with -SO-), an alkanediylsulfonyl group (a group in which -CH- at any position in an alkanediyl group is replaced with -SO-), a cycloalkoxy group, a cycloalkylalkoxy group, an alkoxycarbonyloxy group, an aromatic hydrocarbon group-carbonyloxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy group, and a group in which two or more of these groups are combined.

[0145] Examples of the alkoxy group include alkoxy groups having 1 to 35 carbon atoms, such as a methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 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 even more preferably 1 to 3.

[0146] The alkoxycarbonyl group, alkylcarbonyl group and alkylcarbonyloxy group represent groups in which a carbonyl group or carbonyloxy group is bonded to the above-mentioned alkyl group or alkoxy group.

[0147] Examples of the alkoxycarbonyl group include alkoxycarbonyl groups having 2 to 35 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, and a butoxycarbonyl group. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 36 carbon atoms, such as an acetyl group, a propionyl group, and a butyryl group. Examples of the alkylcarbonyloxy group include alkylcarbonyloxy groups having 2 to 35 carbon atoms, such as an acetyloxy group, a propionyloxy group, and a butyryloxy group. 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.

[0148] Examples of the alkylthio group include alkylthio groups having 1 to 35 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, an undecylthio 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.

[0149] Examples of the alkylsulfonyl group include alkylsulfonyl groups having 1 to 35 carbon atoms, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, an octylsulfonyl group, a 2-ethylhexylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl 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.

[0150] Examples of the alkanediyloxy group include alkanediyloxy groups having 1 to 35 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.

[0151] Examples of the alkanediyloxycarbonyl group include alkanediyloxycarbonyl groups having 2 to 35 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 36 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 35 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.

[0152] Examples of the alkanediylthio group include alkanediylthio groups having 1 to 35 carbon atoms, such as a methylenethio group, an ethylenethio group, a propylenethio 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.

[0153] Examples of the alkanediylsulfonyl group include alkanediylsulfonyl groups having 1 to 35 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.

[0154] Examples of cycloalkoxy groups include cycloalkoxy groups having 3 to 35 carbon atoms, such as a cyclohexyloxy group. Examples of cycloalkylalkoxy groups include cycloalkylalkoxy groups having 4 to 36 carbon atoms, such as a cyclohexylmethoxy group. Examples of alkoxycarbonyloxy groups include alkoxycarbonyloxy groups having 2 to 34 carbon atoms, such as a butoxycarbonyloxy group. Examples of aromatic hydrocarbon group-carbonyloxy groups include aromatic hydrocarbon group-carbonyloxy groups having 7 to 35 carbon atoms, such as a benzoyloxy group. Examples of aromatic hydrocarbon group-carbonyl groups include aromatic hydrocarbon group-carbonyl groups having 7 to 36 carbon atoms, such as a benzoyl group. Examples of aromatic hydrocarbon group-oxy groups include aromatic hydrocarbon group-oxy groups having 6 to 35 carbon atoms, such as a phenyloxy group.

[0155] Examples of groups in which -CH2- in an alicyclic hydrocarbon group is replaced with -O-, -S-, -SO2-, -SO-, or -CO- include the groups shown below. Also included are groups in which, among the groups shown below, -O- is replaced with -S-, and -CO- is replaced with -SO- or -SO2-. The bonding site can be at any position.

[0156] [ka]

[0157] R 4 , R 7 , R 8 and R 9Examples of the substituent that the hydrocarbon group may have include a halogen atom, a cyano group, and a nitro group. Examples of the halogen atom include the same groups as those mentioned above.

[0158] R 4 , R 7 , R 8 and R 9 is a hydrocarbon group having a halogen atom, R 4 , R 7 , R 8 and R 9 Examples of the hydrocarbon group having a halogen atom include a chain hydrocarbon group having a halogen atom (such as a haloalkyl group), an alicyclic hydrocarbon group having a halogen atom, and an aromatic hydrocarbon group having a halogen atom.

[0159] Examples of the alkyl group having a halogen include haloalkyl groups having 1 to 12 carbon atoms, such as fluorinated alkyl groups having 1 to 12 carbon atoms, chlorinated alkyl groups having 1 to 12 carbon atoms, brominated alkyl groups having 1 to 12 carbon atoms, and iodinated alkyl groups having 1 to 12 carbon atoms. Examples of the haloalkyl group include perfluoroalkyl groups having 1 to 12 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 9, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3.

[0160] -CH2- in the haloalkyl group may be replaced by -O- or -CO- or the like, and examples thereof include a haloalkoxy group, a haloalkoxycarbonyl group, a haloalkylcarbonyl group, a haloalkylcarbonyloxy group, etc. Specific examples include a haloalkoxy group having 1 to 11 carbon atoms, a haloalkoxycarbonyl group having 2 to 11 carbon atoms, a haloalkylcarbonyl group having 2 to 12 carbon atoms, a haloalkylcarbonyloxy group having 2 to 11 carbon atoms, etc., and examples thereof include groups in which one or more hydrogen atoms of the above-exemplified groups have been replaced with a halogen atom.

[0161] The hydrocarbon group may have one or more substituents. R 4 The bonding position of the benzene ring to which X is bonded is + In the benzene ring to which X is attached, + The bonding position of R may be ortho, meta, or para. 4 The benzene ring to which is attached is X + It is preferably bonded at the para or meta position relative to the bonding position of (I), and more preferably at the para position.

[0162] m4 is preferably 0, 1, 2, 3 or 4, more preferably 0, 1, 2 or 3, and even more preferably 0, 1 or 2. R 4 The bonding position of to the benzene ring is X + When m4 is 1 or 2, at least one R 4 is X + is preferably bonded at the para or meta position relative to the bonding position of the benzene ring to which R is bonded. 4 is X + is preferably bonded at the ortho- or meta-position relative to the bonding position of the benzene ring to which it is bonded.

[0163] m7 is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2, and even more preferably 0 or 1. R 7 The bonding position of to the benzene ring is X + The bonding position of at least one R may be ortho, meta or para. 7 But X + It is preferably bonded at the ortho- or meta-position relative to the bonding position of (I), and more preferably bonded at the meta-position.

[0164] m8 is preferably 0, 1, 2, 3 or 4, more preferably 0, 1, 2 or 3, even more preferably 0, 1 or 2, and even more preferably 0 or 1.

[0165] m9 is preferably 0, 1, 2, 3 or 4, more preferably 0, 1, 2 or 3, even more preferably 0, 1 or 2, and even more preferably 0 or 1.

[0166] When at least one of m8 and m9 is an integer of 1 or more, R 8 and / or R 9 The bonding position of to the benzene ring is X + The bonding position of at least one R may be ortho, meta or para. 8 and / or R 9 But X + It is preferably bonded at the meta or para position relative to the bonding position of (I), and more preferably at the para position.

[0167] R 4is preferably a halogen atom or an alkyl group having 1 to 12 carbon atoms which may have a halogen atom (-CH2- contained in the alkyl group may be replaced with -O- or -CO-), more preferably a halogen atom, a fluorinated alkyl group having 1 to 6 carbon atoms or an alkyl group having 1 to 6 carbon atoms (-CH2- contained in the fluorinated alkyl group or the alkyl group may be replaced with -O- or -CO-), and more preferably a halogen atom, a fluorinated alkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms (the fluorinated An alkyl group or —CH2— contained in the alkyl group may be replaced with —O— or —CO— is more preferred, a fluorine atom, a bromine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 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 a fluorine atom, an iodine atom, a trifluoromethyl group, a hydroxy group, a methoxy group, a methyl group or a t-butyl group is even more preferred.

[0168] R 7 , R 8 and R 9are each independently preferably a halogen atom or an alkyl group having 1 to 12 carbon atoms which may have a halogen atom (-CH2- contained in the alkyl group may be replaced with -O- or -CO-), more preferably a halogen atom, a fluorinated alkyl group having 1 to 6 carbon atoms or an alkyl group having 1 to 6 carbon atoms (-CH2- contained in the fluorinated alkyl group or the alkyl group may be replaced with -O- or -CO-), and more preferably a halogen atom, a fluorinated alkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms ( The alkyl fluoride group or the —CH2— contained in the alkyl group may be replaced with —O— or —CO—. is more preferred, a fluorine atom, a bromine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms (wherein the —CH2— contained in the alkyl group may be replaced with —O— or —CO—). is even more preferred, and a fluorine atom, an iodine atom, a trifluoromethyl group, a hydroxy group, a methoxy group, a methyl group or a t-butyl group is even more preferred.

[0169] In another embodiment, R 8 or R 9 may contain a group having -SO2-, and each independently, -X 1 -R 10 or -X 1 -L 10 -X 2 -R 10 R 8 or R 9 When R contains a group having -SO2-, 1A or R 1B It is preferable that the group is the same as the group having —SO2— contained in

[0170] Specific examples of the cation represented by formula (IC) include cations represented by formula (IC-1) or formula (IC-2) (hereinafter, these may be referred to as "cation (IC-1)" and "cation (IC-2)", respectively).

[0171] [ka]

[0172] [In the formula, all symbols have the same meanings as defined above.] When X is a sulfur atom and m10=1, R 7 and R 8 or R 8 and R 9 are combined to form S + In particular, a ring containing R 8 and R 9 are combined to form S + It is preferable that the cation is a cation represented by formula (IC′).

[0173] [ka]

[0174] [where, X 7 The symbols other than the above have the same meanings as above. X 7 represents a single bond, -CH2-, -O-, -CO-, -SO-, -SO2- or -S-.

[0175] m8-1 represents an integer of 0 to 4, and when m8-1 is 2 or more, a plurality of R 8 may be the same or different from each other. m9-1 represents an integer of 0 to 4, and when m9-1 is 2 or more, a plurality of R 8 may be the same or different from each other.] X 7 is preferably a single bond, —CH 2 — or —O—.

[0176] Examples of the cation of the salt (I) include cations represented by the following formulae (Ic-1) to (Ic-50).

[0177] [ka]

[0178] [ka]

[0179] [ka]

[0180] [Anion (I)] In formula (I), X 0 Examples of the hydrocarbon group represented by the formula include aliphatic hydrocarbon groups (chain hydrocarbon groups such as alkyl groups, alkenyl groups, and alkynyl groups, and alicyclic hydrocarbon groups), aromatic hydrocarbon groups, and groups combining these. The -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO-, or -SO2-. In the hydrocarbon group, CO2 - The atom adjacent to is preferably a carbon atom, and in the aliphatic hydrocarbon group, CO - The atom adjacent to is more preferably a carbon atom. The number of carbon atoms in the hydrocarbon group is, for example, 2 to 64, may be 2 to 48, is preferably 2 to 36, more preferably 2 to 30, still more preferably 2 to 24, still more preferably 2 to 18, and still more preferably 2 to 12.

[0181] Examples of the alkyl group include linear or branched alkyl groups, such as 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 2 to 18, more preferably 2 to 12, still more preferably 2 to 9, still more preferably 2 to 6, and still more preferably 2 to 4.

[0182] Examples of the alkenyl group include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups.

[0183] Examples of the alkynyl group include an ethynyl group, a propynyl group, an isopropynyl group, a butynyl group, an isobutynyl group, a tert-butynyl group, a pentynyl group, a hexynyl group, an octynyl group, and a nonynyl group.

[0184] The chain hydrocarbon group may have 2 to 36 carbon atoms, preferably 2 to 18 carbon atoms, more preferably 2 to 12 carbon atoms, even more preferably 2 to 9 carbon atoms, still more preferably 2 to 6 carbon atoms, and even more preferably 2 to 4 carbon atoms.

[0185] Examples of groups in which -CH2- in a chain hydrocarbon group is replaced by -O-, -S-, -CO- 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 -CO-), a thio group (a group in which -CH2- in a methylene group is replaced by -S-), Sulfonyl group (a group in which -CH2- in a methylene group is replaced with -SO2-), oxy group (a group in which -CH2- in a methylene group is replaced with -O-), 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-), alkylcarbonyloxy group (an alkyl alkylthio groups (groups in which -CH2- at any position in an alkyl group is replaced with -S-), alkylsulfonyl groups (groups in which -CH2- at any position in an alkyl group is replaced with -SO2-), alkanediyloxy groups (groups in which -CH2- at any position in an alkanediyl group is replaced with -O-), alkanediyloxycarbonyl groups (groups in which -CH2-CH2- at any position in an alkanediyl group is replaced with -O-CO- substituted with -CO-), an alkanediylcarbonyl group (an alkanediyl group in which -CH- at any position is replaced with -CO-), an alkanediylcarbonyloxy group (an alkanediyl group in which -CH-CH- at any position is replaced with -CO-O-), an alkanediylsulfonyl group (an alkanediyl group in which -CH- at any position is replaced with -SO-), and an alkanediylthio group (an alkanediyl group in which -CH- at any position is replaced with -S-).

[0186] Examples of the alkoxy group include alkoxy groups having 1 to 71 carbon atoms, such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, undecyloxy, and phenyloxy groups. The number of carbon atoms in the alkoxy group is, for example, 1 to 36, 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.

[0187] Examples of the alkoxycarbonyl group include alkoxycarbonyl groups having 2 to 71 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, and a butoxycarbonyl group; examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 72 carbon atoms, such as an acetyl group, a propionyl group, and a butyryl group; and examples of the alkylcarbonyloxy group include alkylcarbonyloxy groups having 2 to 71 carbon atoms, such as an acetyloxy group, a propionyloxy group, and a butyryloxy group. The number of carbon atoms in the alkoxycarbonyl group, alkylcarbonyl group, and alkylcarbonyloxy group is, for example, 2 to 36, 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 to 3.

[0188] Examples of the alkylthio group include alkylthio groups having 1 to 71 carbon atoms, such as a methylthio group, an ethylthio group, and a propylthio group. The number of carbon atoms in the alkylthio group is, for example, 1 to 36, and may be 1 to 17, preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and still more preferably 1 to 3.

[0189] Examples of the alkylsulfonyl group include alkylsulfonyl groups having 1 to 71 carbon atoms, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, etc. The number of carbon atoms in the alkylsulfonyl group is, for example, 1 to 36, and may be 1 to 17, preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and still more preferably 1 to 3.

[0190] Examples of the alkanediyloxy group, alkanediyloxycarbonyl group, alkanediylcarbonyl group, alkanediylcarbonyloxy group, alkanediylsulfonyl group, and alkanediylthio group include groups in which one hydrogen atom at any position of an alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, alkylcarbonyloxy group, alkylthio group, or alkylsulfonyl group is replaced with a bonding site.

[0191] The substitution in the alkenyl group or alkynyl group may be any of the substitutions in the alkyl group exemplified above, as long as it contains a carbon-carbon double bond or a carbon-carbon triple bond at any position.

[0192] The alicyclic hydrocarbon group may be any of monocyclic, polycyclic, and spiro rings, and may be any of saturated and unsaturated. Examples of the alicyclic hydrocarbon group include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, cyclononyl, cyclodecyl, and cyclododecyl groups, polycyclic cycloalkyl groups such as norbornyl and adamantyl groups, and spiro rings having a cycloalkyl group bonded to a cycloalkyl group, norbornyl group, or adamantyl group via a spiro bond.

[0193] Examples of the alicyclic hydrocarbon group include the following groups: The bonding site can be any position.

[0194] [ka]

[0195] The alicyclic hydrocarbon group may have 3 to 48 carbon atoms, preferably 3 to 36, more preferably 3 to 24, even more preferably 3 to 18, still more preferably 3 to 16, and even more preferably 3 to 12.

[0196] The group in which -CH2- in the alicyclic hydrocarbon group is replaced with -O-, -S-, -CO- or -SO2- may form an ether ring, ketone ring, lactone ring, sultone ring or acetal ring, and specific examples thereof include the following groups. The bonding site can be at any position.

[0197] [ka]

[0198] The alicyclic hydrocarbon group is preferably a group represented by any one of formulas (y1) to (y11), (y44) to (y48), and (y59) to (y61), and more preferably a group represented by any one of formulas (y3), (y4), (y9), and (y11).

[0199] As the group in which -CH2- in the alicyclic hydrocarbon group is replaced with -O-, -S-, -CO- or -SO2-, a group represented by any of formulas (y12) to (y20), (y26), (y27), (y30), (y31), (y39) to (y43), and (y49) to (y71) is preferred, and a group represented by any of formulas (y14), (y15), (y16), (y20), (y26), (y27), (y30), (y31), (y39), (y40), (y42), (y43), (y49) to (y58), and (y62) to (y71) is more preferred.

[0200] Examples of the aromatic hydrocarbon group include aryl groups such as a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, a phenanthryl group, a binaphthyl group, etc. The aromatic hydrocarbon group may have 6 to 48 carbon atoms, preferably 6 to 36, more preferably 6 to 24, still more preferably 6 to 18, even more preferably 6 to 14, and still more preferably 6 to 10.

[0201] In the case of a combined group, the above groups may contain groups with different valences (such as an alkanediyl group, an alkanetriyl group, an alkanetetrayl group, a cycloalkanediyl group, a cycloalkanetriyl group, or a cycloalkanetetrayl group).

[0202] The combined groups are: a group comprising a combination of an alicyclic hydrocarbon group and a chain hydrocarbon group (wherein —CH— contained in the chain hydrocarbon group or the alicyclic hydrocarbon group may be replaced by —O—, —S—, —CO— or —SO—); a group comprising a combination of a chain hydrocarbon group and an aromatic hydrocarbon group (wherein -CH2- in the chain hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), and It represents a group formed by combining an alicyclic hydrocarbon group with an aromatic hydrocarbon group (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-).

[0203] In the group formed by combining these groups, two or more types of alicyclic hydrocarbon groups, chain hydrocarbon groups and aromatic hydrocarbon groups may be combined. Specifically, the combined groups include: Alicyclic hydrocarbon groups such as an adamantylmethylene group and a cyclohexylmethylene group - chain hydrocarbon group-*, (alicyclic hydrocarbon group)2-chain hydrocarbon group-* (-CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), Chain hydrocarbon groups-alicyclic hydrocarbon groups-* such as methyladamantyl group and dimethyladamantyl group, (chain hydrocarbon group)2-alicyclic hydrocarbon group-* (-CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), a chain hydrocarbon group such as a tolyl group or a xylyl group - an aromatic hydrocarbon group -* (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-); chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-* such as a methylcyclohexylmethylene group, (chain hydrocarbon group)2-alicyclic hydrocarbon group-chain hydrocarbon group-*, (chain hydrocarbon group-alicyclic hydrocarbon group)2-chain hydrocarbon group-* (-CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), an aromatic hydrocarbon group such as a benzyl group - a chain hydrocarbon group -* (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-); a chain hydrocarbon group such as a tolylmethyl group-aromatic hydrocarbon group-chain hydrocarbon group-* (wherein -CH2- contained in the chain hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-*, such as methyladamantanemethyleneadamantyl group and di(methyladamantanemethylene)adamantyl group, (chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group)2-alicyclic hydrocarbon group-*, (chain hydrocarbon group-alicyclic hydrocarbon group)2-chain hydrocarbon group-alicyclic hydrocarbon group-*, (chain hydrocarbon group)2-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-* (-CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), Alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-*, (alicyclic hydrocarbon group)2-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-*, (alicyclic hydrocarbon group-chain hydrocarbon group)2-alicyclic hydrocarbon group-chain hydrocarbon group-*, (alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group)2-chain hydrocarbon group-* (-CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), Examples include chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-*, (chain hydrocarbon group)2-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-*, (chain hydrocarbon group-alicyclic hydrocarbon group)2-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-*, (chain hydrocarbon group-alicyclic hydrocarbon group)2-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-*, (chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group)2-alicyclic hydrocarbon group-chain hydrocarbon group-*, (chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group)2-chain hydrocarbon group-* (-CH2- contained in the chain hydrocarbon group and the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), etc. Here, * represents the bonding site to the carbon atom of the carbonyl group.

[0204] X 0 When -CH2- in the hydrocarbon group represented by the formula (I) is replaced with -O-, -S-, -CO- or -SO2-, the number of carbon atoms before the replacement is the total number of carbon atoms in the hydrocarbon group. 0 When a substituent is bonded to a hydrocarbon group represented by the formula: Figure imgf000012_0001, the number of carbon atoms before substitution is the total number of carbon atoms in the hydrocarbon group.

[0205] X 0 The hydrocarbon group represented by the formula (I) may have one or more substituents. Examples of the substituent include a hydroxy group, a halogen atom, a cyano group, and a nitro group. Also, X 0is 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. 0 When -CH2- in the chain hydrocarbon group contained in the hydrocarbon group is replaced with -O-, -CO-, -S- or -SO2-, the hydrocarbon group can essentially have a substituent such as a hydroxy group, a carboxy group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, a thiol group, an alkylthio group or an alkylsulfonyl group.

[0206] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. X 0 The hydrocarbon group represented by formula (aa) is preferably an aliphatic hydrocarbon group having 2 to 72 carbon atoms which may have a substituent (-CH2- contained in the aliphatic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), a hydrocarbon group having 6 to 72 carbon atoms which contains an aromatic hydrocarbon group having 6 to 36 carbon atoms which may have a substituent, a group represented by formula (aa) or a group represented by formula (bb), More preferred are alicyclic hydrocarbon groups which may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), and groups which combine an alicyclic hydrocarbon group with a chain hydrocarbon group (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-, and -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and the alicyclic hydrocarbon group and the chain hydrocarbon group are , which may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group), an aromatic hydrocarbon group which may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group, a group combining an aromatic hydrocarbon group with a chain hydrocarbon group (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and the aromatic hydrocarbon group and the chain hydrocarbon group may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group), a group represented by formula (aa) or a group represented by formula (bb), More preferably, * represents an alicyclic hydrocarbon group (wherein —CH— contained in the alicyclic hydrocarbon group may be replaced by —O—, —S—, —CO— or —SO—, and the alicyclic hydrocarbon group may have a fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group. * represents —COO - represents a bonding site with a carbon atom of the formula (I), *-alicyclic hydrocarbon group-chain hydrocarbon group (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-, and -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and the alicyclic hydrocarbon group and the chain hydrocarbon group may have a fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group. * represents -COO -represents a bonding site with a carbon atom of the formula (I), *-chain hydrocarbon group-alicyclic hydrocarbon group (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-, and the chain hydrocarbon group and the alicyclic hydrocarbon group may have a fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group. * represents -COO - represents a bonding site with a carbon atom of the formula (I), *-aromatic hydrocarbon group (the aromatic hydrocarbon group may have a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group. * represents -COO - represents a bonding site with a carbon atom of the formula (I).), *-aromatic hydrocarbon group-chain hydrocarbon group (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and the aromatic hydrocarbon group may have a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group, and the chain hydrocarbon group may have a fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group. * represents -COO - represents a bonding site with a carbon atom of the formula (I), *-chain hydrocarbon group-aromatic hydrocarbon group (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, the aromatic hydrocarbon group may have a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group, and the chain hydrocarbon group may have a fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group. * represents -COO - represents a bonding site with the carbon atom of formula (aa), a group represented by formula (bb), More preferably, * represents a polycyclic alicyclic hydrocarbon group (wherein —CH— contained in the polycyclic alicyclic hydrocarbon group may be replaced by —O—, —S—, —CO— or —SO—, and the polycyclic alicyclic hydrocarbon group may have a fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group). * represents —COO -represents a bonding site with a carbon atom of the formula (I), *-polycyclic alicyclic hydrocarbon group-chain hydrocarbon group (-CH2- contained in the polycyclic alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-, and -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and the polycyclic alicyclic hydrocarbon group and the chain hydrocarbon group may have a fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group. * represents -COO - represents a bonding site with a carbon atom of the formula (I), *-chain hydrocarbon group-polycyclic alicyclic hydrocarbon group (-CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-, and -CH2- contained in the polycyclic alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-, and the chain hydrocarbon group and the polycyclic alicyclic hydrocarbon group may have a fluorine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group. * represents -COO - represents a bonding site with a carbon atom of the formula (I), *-aromatic hydrocarbon group (the aromatic hydrocarbon group may have a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group. * represents -COO - represents a bonding site with the carbon atom of formula (aa), a group represented by formula (bb), Particularly preferred are an adamantyl group, an adamantanone group, a hydroxyadamantyl group, a group combining an adamantyl group with an alkyl group (wherein —CH2— contained in the alkyl group may be replaced with —O— or —CO—), a group represented by formula (Y30F), a phenyl group having a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group, a group represented by formula (aa), or a group represented by formula (bb).

[0207] Also, X 0is preferably an aliphatic hydrocarbon group having 2 to 72 carbon atoms which may have a substituent (-CH2- contained in the aliphatic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-), or a hydrocarbon group having 6 to 72 carbon atoms which contains an aromatic hydrocarbon group having 6 to 36 carbon atoms which may have a substituent (-CH2- contained in the hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-), X 0 represents a halogen atom, an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, or an alicyclic hydrocarbon group having 3 to 36 carbon atoms which may have a hydroxy group (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-), a group in which an alicyclic hydrocarbon group having 3 to 36 carbon atoms is combined with a chain hydrocarbon group having 1 to 18 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-, and -CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and the alicyclic hydrocarbon group and the chain hydrocarbon group are not halogen atoms). and a group combining an aromatic hydrocarbon group having 6 to 36 carbon atoms and a chain hydrocarbon group having 1 to 18 carbon atoms (-CH2- in the chain hydrocarbon group may be replaced by -O- or -CO-, and the aromatic hydrocarbon group and the chain hydrocarbon group may have a halogen atom, an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group).

[0208] Among them, X 0is preferably an alicyclic hydrocarbon group having 3 to 36 carbon atoms, an aromatic hydrocarbon group having 6 to 36 carbon atoms, or a group obtained by combining an acyclic hydrocarbon group having 1 to 18 carbon atoms with an alicyclic hydrocarbon group having 3 to 36 carbon atoms or an aromatic hydrocarbon group having 6 to 36 carbon atoms (the alicyclic hydrocarbon group, the acyclic hydrocarbon group, and the aromatic hydrocarbon group may have a fluorine atom, an iodine atom, a fluorinated alkyl group having 1 to 4 carbon atoms, or a hydroxy group, and -CH2- contained in the alicyclic hydrocarbon group and the acyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, or -SO2-).

[0209] In the above groups, the alicyclic hydrocarbon group has preferably 3 to 36 carbon atoms, more preferably 3 to 24, even more preferably 3 to 18, still more preferably 3 to 16, and even more preferably 3 to 12. The chain hydrocarbon group has preferably 1 to 18 carbon atoms, more preferably 1 to 12, even more preferably 1 to 9, still more preferably 1 to 6, and even more preferably 1 to 4. The aromatic hydrocarbon group has preferably 6 to 36 carbon atoms, more preferably 6 to 24, even more preferably 6 to 18, still more preferably 6 to 14, and even more preferably 6 to 10.

[0210] [ka]

[0211] [In formula (aa), X a and X b each independently represents -O- or -S-. X 1a 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-.

[0212] X 2arepresents a hydrocarbon group having 1 to 48 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-.

[0213] * -COO - represents the bonding site with the carbon atom of [In formula (bb), L A represents an alkanediyl group having 1 to 6 carbon atoms which may have a fluorine atom, or an aromatic hydrocarbon group having 6 to 14 carbon atoms which may have a halogen atom or a perfluoroalkyl group having 1 to 4 carbon atoms.

[0214] L B represents a single bond or an alkanediyl group having 1 to 6 carbon atoms, and -CH2- contained in the alkanediyl group may be replaced by -O-, -S-, -CO- or -SO2-.

[0215] R A represents a hydrocarbon group having 1 to 36 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-.

[0216] * -COO - represents the bonding site with the carbon atom of X a and X b are preferably the same atom, and more preferably both are oxygen atoms.

[0217] X 1a and X 2a Examples of the hydrocarbon group represented by the formula (I) include an aliphatic hydrocarbon group, an aromatic hydrocarbon group, or a group combining two or more of these. These hydrocarbon groups may have a substituent. Furthermore, -CH2- contained in these hydrocarbon groups may be replaced with -O-, -S-, -CO-, or -SO2-. Here, the number of carbon atoms in the hydrocarbon group refers to the number of carbon atoms in the unsubstituted hydrocarbon group that does not have a substituent.

[0218] X 1a Examples of the aliphatic hydrocarbon group include chain hydrocarbon groups such as alkanetriyl groups, alicyclic hydrocarbon groups, and combinations thereof. Specific examples of the alkanetriyl group include a methine 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 decanetriyl group, an undecanetriyl group, and a dodecanetriyl group.

[0219] The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include a cyclobutanetriyl group, a cyclopentanetriyl group, a cyclohexanetriyl group, and a cyclooctanetriyl group.

[0220] Examples of the polycyclic alicyclic hydrocarbon group include a norbornanetriyl group and an adamantanetriyl group. Examples of the aromatic hydrocarbon group include a benzenetriyl group, a naphthalenetriyl group, and an anthracenetriyl group.

[0221] In the case of a combined group, the above groups may contain groups with different valences (such as an alkyl group, an alkanediyl group, an alkanetetrayl group, a cycloalkyl group, a cycloalkanediyl group, or a cycloalkanetetrayl group).

[0222] X 1a The hydrocarbon group represented by the formula (I) has 1 to 24 carbon atoms and may further have one or more substituents. Examples of the substituents include a hydroxy group, a halogen atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkoxycarbonyl group having 2 to 13 carbon atoms, an alkylcarbonyl group having 2 to 13 carbon atoms, an alkylcarbonyloxy group having 2 to 13 carbon atoms, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or a group combining these.

[0223] Examples of the halogen atom, alkyl group, alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, alkylcarbonyloxy group, alicyclic hydrocarbon group, aromatic hydrocarbon group, and combinations thereof include the same groups as those described above.

[0224] X 1a The hydrocarbon group represented by the formula (w1-3) is preferably an alkanetriyl group having 1 to 6 carbon atoms which may have a substituent or an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent, more preferably an alkanetriyl group having 1 to 6 carbon atoms or a group represented by any of formulas (w1-1) to (w1-11), and even more preferably an alkanetriyl group having 1 to 6 carbon atoms, a polycyclic hydrocarbon group such as a group represented by formula (w1-1) or a group represented by formula (w1-3), or a monocyclic hydrocarbon group such as a group represented by formula (w1-2) or a group represented by formula (w1-6).

[0225] [ka]

[0226] [In formulas (w1-1) to (w1-11), The ring may have a hydroxy group, a halogen atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkoxycarbonyl group having 2 to 13 carbon atoms, an alkylcarbonyl group having 2 to 13 carbon atoms, an alkylcarbonyloxy group having 2 to 13 carbon atoms, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or a combination thereof.

[0227] * denotes a binding site.] X 2a The hydrocarbon group represented by the formula (I) preferably has 2 to 48 carbon atoms, more preferably 4 to 48 carbon atoms, even more preferably 6 to 44 carbon atoms, even more preferably 8 to 40 carbon atoms, and even more preferably 10 to 38 carbon atoms.

[0228] X 2aExamples of the substituent that the hydrocarbon group in the formula (I) may have include a hydroxy group, a halogen atom, a cyano group, an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkoxycarbonyl group having 2 to 13 carbon atoms, an alkylcarbonyl group having 2 to 13 carbon atoms, an alkylcarbonyloxy group having 2 to 13 carbon atoms, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or a group combining these.

[0229] Examples of the halogen atom, alkyl group, alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, alkylcarbonyloxy group, alicyclic hydrocarbon group, aromatic hydrocarbon group, and combinations thereof include the same groups as those described above.

[0230] X 2a The hydrocarbon group having 1 to 48 carbon atoms represented by the following formula may have one or more substituents. X 2a The substituent that the hydrocarbon group in the formula (I) may have is preferably a fluorine atom, an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group.

[0231] X 2a Examples of the hydrocarbon group in include linear or branched chain hydrocarbon groups (for example, alkanediyl groups, etc.), monocyclic or polycyclic alicyclic hydrocarbon groups, and aromatic hydrocarbon groups, and may be a combination of two or more of these groups.

[0232] Specific examples include linear alkanediyl groups such as a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, and an octane-1,8-diyl group; branched alkanediyl groups such as 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; monocyclic alicyclic hydrocarbon groups such as monocyclic cycloalkanediyl groups, such as cyclobutane-1,3-diyl, cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, and cyclooctane-1,5-diyl; polycyclic alicyclic hydrocarbon groups such as polycyclic cycloalkanediyl groups such as norbornane-1,4-diyl, norbornane-2,5-diyl, adamantane-1,5-diyl, and adamantane-2,6-diyl; Examples of the aromatic hydrocarbon groups include a phenylene group, a naphthylene group, a biphenylene group, an anthrylene group, a phenanthrylene group, and a binaphthylene group.

[0233] In the case of a combined group, the above groups may contain groups with different valences (such as an alkyl group, an alkanetriyl group, an alkanetetrayl group, a cycloalkyl group, a cycloalkanetriyl group, or a cycloalkanetetrayl group).

[0234] Examples of the combined group include a group in which a chain hydrocarbon group and an alicyclic hydrocarbon group are combined, a group in which a chain hydrocarbon group and an aromatic hydrocarbon group are combined, and a group in which an alicyclic hydrocarbon group and an aromatic hydrocarbon group are combined. Specific examples include a group in which one or more alicyclic hydrocarbon groups are bonded to a chain hydrocarbon group (e.g., -chain hydrocarbon group-alicyclic hydrocarbon group, -chain hydrocarbon group-(alicyclic hydrocarbon group)2, etc.), a group in which one or more chain hydrocarbon groups are bonded to an alicyclic hydrocarbon group (e.g., -alicyclic hydrocarbon group-chain hydrocarbon group, -alicyclic hydrocarbon group-(chain hydrocarbon group)2, etc.), and a group in which one or more alicyclic hydrocarbon groups and chain hydrocarbon groups are bonded to a chain hydrocarbon group (e.g., -chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group, -chain hydrocarbon group-(alicyclic hydrocarbon group-chain hydrocarbon group)2, etc.).

[0235] X 2a The hydrocarbon group in a chain hydrocarbon group having 2 to 18 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and the chain hydrocarbon group may have a substituent); an alicyclic hydrocarbon group having 3 to 18 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-, and the alicyclic hydrocarbon group may have a substituent), or It is preferably a group (which may have a substituent) comprising a combination of a chain hydrocarbon group having 1 to 12 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-) and an alicyclic hydrocarbon group having 3 to 18 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-), a chain hydrocarbon group having 4 to 18 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and the chain hydrocarbon group may have a substituent), or It is more preferable that the group is a combination of a chain hydrocarbon group having 1 to 12 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-) and an alicyclic hydrocarbon group having 3 to 16 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-) (the group may have a substituent), a chain hydrocarbon group having 6 to 14 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced by -O- or -CO-, and the chain hydrocarbon group may have a substituent), or More preferably, it is a group (which may have a substituent) that combines a chain hydrocarbon group having 1 to 12 carbon atoms (-CH2- contained in the chain hydrocarbon group may be replaced with -O- or -CO-) with an alicyclic hydrocarbon group having 5 to 14 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-).

[0236] Specifically, X 2a Examples of the hydrocarbon group in an alkanediyl group having 2 to 18 carbon atoms (-CH- contained in the alkanediyl group may be replaced by -O- or -CO-, and the alkanediyl group may have a substituent); an alicyclic hydrocarbon group having 3 to 18 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-, and the alicyclic hydrocarbon group may have a substituent); a group consisting of an alkanediyl group having 1 to 12 carbon atoms (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-) and an alicyclic hydrocarbon group having 3 to 18 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-) (the group may have a substituent), or It is preferably a group (which may have a substituent) consisting of an alkanediyl group having 1 to 12 carbon atoms (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), an alicyclic hydrocarbon group having 3 to 18 carbon atoms, and an alkyl group having 1 to 12 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-), an alkanediyl group having 4 to 18 carbon atoms (-CH- contained in the alkanediyl group may be replaced by -O- or -CO-, and the alkanediyl group may have a substituent); a group consisting of an alkanediyl group having 1 to 12 carbon atoms (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-) and an alicyclic hydrocarbon group having 3 to 16 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-) (the group may have a substituent), or It is more preferable that the alkyl group is an alkanediyl group having 1 to 12 carbon atoms (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), an alicyclic hydrocarbon group having 3 to 16 carbon atoms, and an alkyl group having 1 to 12 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-), and the alkyl group may have a substituent. an alkanediyl group having 6 to 14 carbon atoms (wherein —CH— contained in the alkanediyl group may be replaced by —O— or —CO—, and the alkanediyl group may have a substituent); a group consisting of an alkanediyl group having 1 to 12 carbon atoms (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-) and an adamantanediyl group (-CH2- contained in the adamantanediyl group may be replaced with -O- or -CO-) (the group may have a substituent), or More preferred are groups (which may have a substituent) consisting of an alkanediyl group having 1 to 12 carbon atoms (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-) and an adamantanediyl group and an alkyl group having 1 to 12 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-).

[0237] More specifically, X 2a is the formula (X 2 -1), a group represented by the formula (X 2 -2), a group represented by the formula (X 2 -3) or a group represented by the formula (X 2 -4) is preferred.

[0238] [ka]

[0239] [Formula(X 2 -1)~Formula(X 2 -4) Medium, R 1x , R2x , R 3x , R 4x , R 5x and R 6x each independently represents an alkyl group having 1 to 6 carbon atoms, an alicyclic hydrocarbon group having 5 to 12 carbon atoms, or a group combining two or more of these groups, and -CH2- contained in the alkyl group and the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, or -SO2-, and the alkyl group and the alicyclic hydrocarbon group may have a substituent.

[0240] * is X a and X b represents the binding site with The combined group may be a combination of one alkyl group and one alicyclic hydrocarbon group described above, or two or more of either one or two or more of both. In this case, the number of carbon atoms in the combined group is 39 or less, and preferably 37 or less.

[0241] Among them, R 1x , R 2x , R 3x , R 4x , R 5x and R 6xExamples thereof include an alkyl group having 1 to 6 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-, and the alkyl group may have a substituent), an alicyclic hydrocarbon group having 5 to 12 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-, and the alicyclic hydrocarbon group may have a substituent), or a combination of an alkyl group having 1 to 6 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-) and an alicyclic hydrocarbon group having 5 to 12 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group and more preferably a group (which may have a substituent) combining a methoxy group, an adamantyl group (wherein —CH— may be replaced by —O— or —CO— and the adamantyl group may have a substituent), or an alkyl group having 1 to 6 carbon atoms (wherein —CH— may be replaced by —O— or —CO—).

[0242] The group represented by formula (aa) is more preferably a group represented by any one of the following formulas (aa1), (aa2), (aa3) and (aa4).

[0243] [ka]

[0244] [In formula (aa1) to formula (aa4), W 1a represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms. X a and X b Each of X independently represents -O- or -S-. a and X b is W 1a It bonds to the same carbon atom contained in

[0245] R 1x , R 2x , R 3x , R 4x , R 5x and R 6x are each independently a group of the formula (X 2 -1), formula (X 2 -2), formula (X 2 -3) and the formula (X 2 -4) has the same meaning. * -COO - represents the bonding site with the carbon atom of In formulas (aa1) to (aa4), W 1a The alicyclic hydrocarbon group is more preferably a group represented by formula (w1-1) to formula (w1-11), and even more preferably a polycyclic hydrocarbon group such as a group represented by formula (w1-1) or a group represented by formula (w1-3), or a monocyclic hydrocarbon group such as a group represented by formula (w1-2) or a group represented by formula (w1-6).

[0246] In formula (bb), L A and L B Examples of the alkanediyl group having 1 to 6 carbon atoms 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, 1-methylpropane-1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, 1-methylbutane-1,4-diyl, and 2-methylbutane-1,4-diyl. The number of carbon atoms in the alkanediyl group is preferably 1 to 4, and more preferably 1 to 3.

[0247] Examples of the alkanediyl group which may have a fluorine atom include perfluoroalkanediyl groups such as a difluoromethylene group, a perfluoroethylene group, a perfluoropropanediyl group, a perfluorobutanediyl group, and a perfluoropentanediyl group.

[0248] When -CH2- in the alkanediyl group is replaced with -O-, -S-, -CO- or -SO2-, the number of carbon atoms before replacement is defined as the total number of carbon atoms in the alkanediyl group. The alkanediyl group includes 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 alkoxy group (a group in which -CH2- at any position in an alkyl group is replaced with -O-), an alkoxycarbonyl group (a group in which -CH2-CH2- at any position in an alkyl group is replaced with -O-CO-), 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 alkylthio group (a group in which -CH2- at any position in an alkyl group is replaced with -S-), an alkylsulfonyl group ( an alkanediyloxy group (an alkanediyl group in which any -CH2- at any position is replaced with -SO2-), an alkanediyloxycarbonyl group (an alkanediyl group in which any -CH2- at any position is replaced with -O-), an alkanediylcarbonyl group (an alkanediyl group in which any -CH2- at any position is replaced with -O-CO-), an alkanediyloxycarbonyl group (an alkanediyl group in which any -CH2- at any position is replaced with -O-CO-), an alkanediyloxycarbonyl group (an alkanediyl group in which any -CH2- at any position is replaced with -O-CO-), an alkanediyloxycarbonyl group (an alkanediyl group in which any -CH2- at any position is replaced with -O-CO-), an alkanediyloxycarbonyl group (an alkanediyl group in which any -CH2- at any position is replaced with -O-CO-), an alkanediyloxycarbonyl group (an alkanediyloxycarbon ... or -CO-), an alkanediylcarbonyloxy group (a group in which -CH2-CH2- at any position in an alkanediyl group is replaced with -CO-O-)), an alkanediylthio group (a group in which -CH2- at any position in an alkanediyl group is replaced with -S-), or an alkanediylsulfonyl group (a group in which -CH2- at any position in an alkanediyl group is replaced with -SO2-).

[0249] Examples of the alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, alkylcarbonyloxy group, alkylthio group and alkylsulfonyl group are the same as those mentioned above. Examples of the alkanediyloxy group include a methyleneoxy group, an ethyleneoxy group, a propanediyloxy group, a butanediyloxy group, and a pentanediyloxy group.

[0250] Examples of the alkanediyloxycarbonyl group include a methyleneoxycarbonyl group, an ethyleneoxycarbonyl group, a propanediyloxycarbonyl group, and a butanediyloxycarbonyl group.

[0251] Examples of the alkanediylcarbonyl group include a methylenecarbonyl group, an ethylenecarbonyl group, a propanediylcarbonyl group, a butanediylcarbonyl group, and a pentanediylcarbonyl group.

[0252] Examples of the alkanediylcarbonyloxy group include a methylenecarbonyloxy group, an ethylenecarbonyloxy group, a propanediylcarbonyloxy group, and a butanediylcarbonyloxy group.

[0253] Examples of the alkanediylthio group include a methylenethio group, an ethylenethio group, a propanediylthio group, a butanediylthio group, and a pentanediylthio group. Examples of the alkanediylsulfonyl group include a methylenesulfonyl group, an ethylenesulfonyl group, a propanediylsulfonyl group, a butanediylsulfonyl group, and a pentanediylsulfonyl group.

[0254] L A Examples of the aromatic hydrocarbon group having 6 to 14 carbon atoms include aromatic hydrocarbon groups such as arylene groups such as a phenylene group, a naphthylene group, an anthrylene group, a biphenylene group, and a phenanthrylene group. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 10, and more preferably 6.

[0255] L A Examples of the halogen atom that may be contained in include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. LA Examples of the perfluoroalkyl group having 1 to 4 carbon atoms that may be contained in the aryloxy group include a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, and a nonafluorobutyl group.

[0256] L A is preferably an alkanediyl group having 1 to 4 carbon atoms which may have a fluorine atom, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a halogen atom or a perfluoroalkyl group having 1 to 4 carbon atoms, and more preferably an alkanediyl group having 1 to 3 carbon atoms which may have a fluorine atom, or a phenylene group which may have a fluorine atom, an iodine atom, or a perfluoroalkyl group having 1 to 3 carbon atoms.

[0257] L B is preferably a single bond or an alkanediyl group having 1 to 3 carbon atoms (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), and more preferably a single bond, a methylene group or an ethylene group.

[0258] R A Examples of the hydrocarbon group in include aliphatic hydrocarbon groups (chain hydrocarbon groups such as alkyl groups, alkenyl groups, and alkynyl groups, and alicyclic hydrocarbon groups), aromatic hydrocarbon groups, and groups formed by combining these.

[0259] 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, an n-pentyl group, an n-hexyl group, an n-heptyl group, a 2-ethylhexyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, etc. The number of carbon atoms in the alkyl group is preferably 1 to 18, more preferably 1 to 12, even more preferably 1 to 9, still more preferably 1 to 6, and even more preferably 1 to 4.

[0260] Examples of the alkenyl group include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups.

[0261] Examples of the alkynyl group include an ethynyl group, a propynyl group, an isopropynyl group, a butynyl group, an isobutynyl group, a tert-butynyl group, a pentynyl group, a hexynyl group, an octynyl group, and a nonynyl group.

[0262] Examples of groups in which -CH2- in a chain hydrocarbon group is replaced with -O-, -S-, -CO- or -SO2- include a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkylsulfonyl group, and an alkylthio group.

[0263] Examples of the alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, alkylcarbonyloxy group, alkylsulfonyl group and alkylthio group include an alkoxy group having 1 to 17 carbon atoms, an alkoxycarbonyl group having 2 to 17 carbon atoms, an alkylcarbonyl group having 2 to 18 carbon atoms, an alkylcarbonyloxy group having 2 to 17 carbon atoms, an alkylsulfonyl group having 1 to 17 carbon atoms and an alkylthio group having 1 to 17 carbon atoms, and examples thereof include the same groups as those described above.

[0264] The alicyclic hydrocarbon group may be monocyclic, polycyclic, or spirocyclic, and may be saturated or unsaturated. Examples of the monocyclic alicyclic hydrocarbon group include monocyclic cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and cyclododecyl. Examples of the polycyclic alicyclic hydrocarbon group include polycyclic cycloalkyl groups such as decahydronaphthyl, adamantyl, and norbornyl.

[0265] Specific examples of the alicyclic hydrocarbon group and the group in which -CH2- contained in the alicyclic hydrocarbon group is replaced with -O-, -S-, -CO- or -SO2- include groups represented by the above formulae (y1) to (y71). The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 36, more preferably 3 to 24, even more preferably 3 to 18, still more preferably 3 to 16, and even more preferably 3 to 12.

[0266] Examples of the aromatic hydrocarbon group include aryl groups such as 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 36, more preferably 6 to 24, still more preferably 6 to 18, even more preferably 6 to 14, and still more preferably 6 to 10.

[0267] In the case of a combined group, the above groups may contain groups with different valences (such as an alkanediyl group, an alkanetriyl group, a cycloalkanediyl group, or a cycloalkanetriyl group).

[0268] Groups formed by combination include groups combining an aromatic hydrocarbon group with a chain hydrocarbon group (e.g., aromatic hydrocarbon group-alkanediyl group-*, alkyl group-aromatic hydrocarbon group-*), groups combining an alicyclic hydrocarbon group with a chain hydrocarbon group (e.g., alicyclic hydrocarbon group-alkanediyl group-*, alkyl group-alicyclic hydrocarbon 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.

[0269] 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.

[0270] 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.

[0271] 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.

[0272] Examples of the aromatic hydrocarbon group-alicyclic hydrocarbon group-* include a phenyladamantyl group. Examples of the alicyclic hydrocarbon group-aromatic hydrocarbon group-* include an adamantylphenyl group.

[0273] In the group formed by combining these, two or more types of alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may be combined. B may be bound to

[0274] In addition to the groups mentioned above, examples of groups in which -CH2- in a hydrocarbon group is replaced with -O-, -S-, -CO-, or -SO2- include cycloalkoxy groups, cycloalkylalkoxy groups, alkoxycarbonyloxy groups, aromatic hydrocarbon group-carbonyloxy groups, and groups in which two or more of these groups are combined.

[0275] Examples of cycloalkoxy groups include cycloalkoxy groups having 3 to 17 carbon atoms, such as a cyclohexyloxy group. Examples of cycloalkylalkoxy groups include cycloalkylalkoxy groups having 4 to 17 carbon atoms, such as a cyclohexylmethoxy group. Examples of alkoxycarbonyloxy groups include alkoxycarbonyloxy groups having 2 to 16 carbon atoms, such as a butoxycarbonyloxy group. Examples of aromatic hydrocarbon group-carbonyloxy groups include aromatic hydrocarbon group-carbonyloxy groups having 7 to 17 carbon atoms, such as a benzoyloxy group.

[0276] When a -CH2- in a hydrocarbon group is replaced with -O-, -S-, -SO2-, or -CO-, the total number of carbon atoms in the hydrocarbon group is the number of carbon atoms before the replacement, which may be 1 or 2 or more.

[0277] R A Examples of the substituent that the hydrocarbon group may have include a halogen atom, a cyano group, and an alkyl group having 1 to 12 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O-, -S-, -CO- or -SO2-).

[0278] Examples of the halogen atom include the same groups as those mentioned above. Examples of the alkyl group having 1 to 12 carbon atoms include the same groups as those mentioned above. Examples of groups in which -CH2- 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, and an alkylcarbonyloxy group.

[0279] Examples of the alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, and alkylcarbonyloxy group include alkoxy groups having 1 to 11 carbon atoms, alkoxycarbonyl groups having 2 to 11 carbon atoms, alkylcarbonyl groups having 2 to 12 carbon atoms, and alkylcarbonyloxy groups having 2 to 11 carbon atoms, and include, for example, the same groups as those described above.

[0280] R A The hydrocarbon group in may have one or more substituents. R A The hydrocarbon group in is preferably an alkyl group having 1 to 12 carbon atoms which may have a substituent (provided that -CH2- contained in the alkyl group may be replaced with -O-, -S-, -CO- or -SO2-), or a cyclic hydrocarbon group having 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-), and more preferably a cyclic hydrocarbon group having 3 to 18 carbon atoms which may have a fluorine atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, or a perfluoroalkyl group having 1 to 6 carbon atoms (provided that -CH2- contained in the cyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO2-).

[0281] Examples of the cyclic hydrocarbon group include cyclic hydrocarbon groups such as monocyclic or polycyclic alicyclic hydrocarbon groups having 3 to 18 carbon atoms and aromatic hydrocarbon groups having 6 to 18 carbon atoms, or combinations of these groups.

[0282] Examples of the alicyclic hydrocarbon group, aromatic hydrocarbon group, and combined group include the same groups as those described above. In the group formed by the combination, two or more types of alicyclic hydrocarbon groups and two or more types of aromatic hydrocarbon groups may be combined. B may be bound to

[0283] A cyclic hydrocarbon group having 3 to 18 carbon atoms (the cyclic hydrocarbon group may have a fluorine atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, or a perfluoroalkyl group having 1 to 6 carbon atoms, and -CH2- contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, or -SO2-) is an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a fluorine atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, or a perfluoroalkyl group having 1 to 4 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO-, or -SO2-), or It is preferably an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a fluorine atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms or a perfluoroalkyl group having 1 to 4 carbon atoms, More preferably, it is an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a fluorine atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, or a perfluoroalkyl group having 1 to 4 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced with -O- or -CO-).

[0284] The group represented by formula (bb) is more preferably a group represented by formula (bb1).

[0285] [ka]

[0286] [In formula (bb1), L A and L B has the same meaning as formula (bb). W 2a represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms, which may have a fluorine atom, an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, or a hydroxy group, and -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-.

[0287] * -COO - represents the bonding site with the carbon atom of In equation (bb1), W 2ais more preferably an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a fluorine atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms or a perfluoroalkyl group having 1 to 4 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -CO- or -SO2-).

[0288] Preferred alicyclic hydrocarbon groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, and the following groups (the bonding site may be any position): and preferred aromatic hydrocarbon groups include phenyl and naphthyl groups.

[0289] [ka]

[0290] Examples of the carboxylate anion in the carboxylate salt represented by formula (I) include the carboxylate anions described below.

[0291] [ka]

[0292] [ka]

[0293] [ka]

[0294] Specific examples of the carboxylate (I) include salts of any combination of the above-mentioned cations and anions. Specific examples of the carboxylate (I) are shown in the table below. In the table below, each symbol represents the symbol attached to the structure representing the above-mentioned anion or cation, and "~" indicates that the carboxylate (I) corresponds to the anion (I). For example, carboxylate (I-1) is a salt consisting of an anion represented by formula (Ia-1) and a cation represented by formula (Ic-1), carboxylate (I-2) is a salt consisting of an anion represented by formula (Ia-2) and a cation represented by formula (Ic-1), and carboxylate (I-101) is a salt consisting of an anion represented by formula (Ia-1) and a cation represented by formula (Ic-2).

[0295] [ka]

[0296] [Table 1] JPEG2025071080000040.jpg63170

[0297] Among these, as the carboxylate (I), a salt obtained by combining an anion represented by any one of formulas (Ia-1) to (Ia-5), (Ia-10) to (Ia-21), and (Ia-57) to (Ia-66) with a cation represented by any one of formulas (Ic-1) to (Ic-50) is preferred.

[0298] <Method for producing carboxylate (I)> The carboxylate (I) can be produced by reacting a salt represented by formula (Ia) with a salt represented by formula (Ib) in a solvent.

[0299] [ka]

[0300] wherein all symbols have the same meanings as defined above. R A , R B and RC each independently represents a hydrocarbon group having 1 to 12 carbon atoms, or R A , R B and R C may combine to form an aromatic ring. D represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms.] Examples of solvents used in this reaction include chloroform, acetonitrile, and ion-exchanged water.

[0301] The reaction temperature is usually 15° C. to 80° C., and the reaction time is usually 0.5 to 24 hours. The salt represented by formula (Ib) can be synthesized with reference to the methods described in JP-A Nos. 2011-39502 and 2014-88367, and examples thereof include salts represented by the following formulas.

[0302] [ka]

[0303] In the salt (Ia), R 1A But *-OL 10 -CO-OR 10 The salt represented by formula (I-a1) can be produced by reacting a salt represented by formula (Ic) with a compound represented by formula (Id) in a solvent in the presence of a base catalyst.

[0304] [ka]

[0305] [In the formula, all symbols have the same meanings as defined above.] Examples of the base include potassium carbonate, potassium iodide, pyridine, and triethylamine.

[0306] Examples of the solvent include chloroform, monochlorobenzene, dimethylformamide, acetonitrile, ethyl acetate, and water. The reaction temperature is usually 15° C. to 80° C., and the reaction time is usually 0.5 to 24 hours.

[0307] Examples of compounds represented by formula (Id) include the compounds represented below, which are readily available on the market and can also be easily produced by known production methods.

[0308] [ka]

[0309] The salt represented by formula (Ic) can be produced by passing the salt represented by formula (Ic') through an ion exchange resin.

[0310] [ka]

[0311] [In the formula, all symbols have the same meanings as defined above.] Examples of ion exchange resins include ion exchange resin (No. 6, 100-200 mesh, manufactured by Wako Pure Chemical Industries, Ltd.).

[0312] The solvent may be methanol or the like. When X is a sulfur atom, the salt represented by formula (Ic′) can be produced by reacting a compound represented by formula (Ie) with a compound represented by formula (If) in a solvent in the presence of trifluoroacetic anhydride and trifluoromethanesulfonic acid, followed by treating with a base.

[0313] [ka]

[0314] [In the formula, all symbols have the same meanings as defined above.] Examples of the solvent include chloroform, monochlorobenzene, and acetonitrile.

[0315] The reaction temperature is usually 15° C. to 100° C., and the reaction time is usually 0.5 to 24 hours. Examples of the compound represented by formula (Ie) include compounds represented by the following formula, which are readily available on the market.

[0316] [ka]

[0317] Examples of the compound represented by formula (If) include compounds represented by the following formula, which are readily available on the market.

[0318] [ka]

[0319] When X is an iodine atom, the salt represented by formula (Ic) can be produced by reacting a compound represented by formula (Ig) with a compound represented by formula (If) in a solvent in the presence of potassium peroxymonosulfate and sulfuric acid, followed by treatment with hydrochloric acid.

[0320] [ka]

[0321] [In the formula, all symbols have the same meanings as defined above.] Examples of the solvent include chloroform, monochlorobenzene, and acetonitrile.

[0322] The reaction temperature is usually 15° C. to 100° C., and the reaction time is usually 0.5 to 24 hours. Examples of the compound represented by formula (Ig) include compounds represented by the following formula, which are readily available on the market.

[0323] [ka]

[0324] In the salt (Ia), R 1A But *-OR 10 The salt represented by formula (I-a2) can be produced by reacting a salt represented by formula (Ic) with a compound represented by formula (I-d1) in a solvent in the presence of a catalyst.

[0325] [ka]

[0326] [wherein all symbols have the same meanings as defined above, X X represents a hydroxy group or a chlorine atom. Examples of the catalyst include carbonyldiimidazole, potassium carbonate, potassium iodide, pyridine, triethylamine, potassium hydroxide, and sodium hydroxide.

[0327] Examples of the solvent include chloroform, monochlorobenzene, dimethylformamide, acetonitrile, ethyl acetate, and water. The reaction temperature is usually 15° C. to 80° C., and the reaction time is usually 0.5 to 24 hours.

[0328] Examples of compounds represented by formula (I-d1) 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.

[0329] [ka]

[0330] In the salt (Ia), R 1A But *-O-CO-OR 10The salt represented by formula (I-a3) can be produced by reacting a salt represented by formula (Ic) with a compound represented by formula (I-d2) in a solvent in the presence of carbonyldiimidazole.

[0331] [ka]

[0332] [In the formula, all symbols have the same meanings as defined above.] Examples of the solvent include chloroform, monochlorobenzene, dimethylformamide, acetonitrile, ethyl acetate, and water.

[0333] The reaction temperature is usually 15° C. to 80° C., and the reaction time is usually 0.5 to 24 hours. Compounds represented by formula (I-d2) include corresponding compounds among compounds represented by formula (I-d1), and are readily available on the market or can be easily produced by known production methods.

[0334] In the salt (Ia), R 1A But *-O-CO-R 10 The salt represented by formula (I-a4) can also be produced by reacting a salt represented by formula (Ic) with a compound represented by formula (I-d3) in a solvent in the presence of a catalyst.

[0335] [ka]

[0336] [In the formula, all symbols have the same meanings as defined above.] Examples of the catalyst include carbonyldiimidazole, potassium carbonate, potassium iodide, pyridine, triethylamine, potassium hydroxide, and sodium hydroxide.

[0337] Examples of the solvent include chloroform, monochlorobenzene, dimethylformamide, acetonitrile, ethyl acetate, and water. The reaction temperature is usually 15° C. to 80° C., and the reaction time is usually 0.5 to 24 hours.

[0338] Examples of the compound represented by formula (I-d3) include the compounds represented by the following formula, which are readily available on the market.

[0339] [ka]

[0340] In the salt (Ia), R 1B But *-OL 10 -CO-OR 10 , *-OR 10 or *-O-CO-OR 10 and a salt R 1A and R 1B But *-OL 10 -CO-OR 10 , *-OR 10 or *-O-CO-OR 10 The salts R 1A *-OL 10 -CO-OR 10 , *-OR 10 or *-O-CO-OR 10 In the reaction scheme used in the example of the production method of the salt, the salt represented by formula (1-c) can be replaced with a salt represented by the following formula (Ic'') or (Ic''').

[0341] [ka]

[0342] [In the formula, all symbols have the same meanings as defined above.] [Carboxylic Acid Generator] The carboxylic acid generator of the present invention is an acid generator containing a carboxylic acid salt (I). The carboxylic acid salt (I) of the present invention can function as an acid generator or a quencher in a resist composition. When the carboxylic acid salt (I) is used as an acid generator or a quencher in a resist composition, the acid generator or quencher may contain only one type of carboxylic acid salt (I) or two or more types of carboxylic acid salts (I).

[0343] [Resist Composition] The resist composition of the present invention may further contain a carboxylic acid generator containing the carboxylate (I) of the present invention, an acid generator known in the resist field other than the carboxylic acid generator containing the carboxylate (I) (hereinafter sometimes referred to as "acid generator (B)") and / or a carboxylic acid generator known in the resist field other than the carboxylate (I). The acid generator (B) and the carboxylate other than the carboxylate (I) may use one type alone, or two or more types may be used in combination.

[0344] When the carboxylic acid generator of the present invention contains a carboxylic acid salt other than the acid generator (B) and / or the carboxylic acid salt (I), the content ratio (mass ratio) of the carboxylic acid salt (I) to the acid generator (B) and / or the carboxylic acid salt other than the carboxylic acid salt (I) is usually 1:99 to 100:0, preferably 1:99 to 99:1, more preferably 2:98 to 98:2, and even more preferably 5:95 to 95:5.

[0345] In the resist composition of the present invention, the content of the carboxylate (I) is preferably from 0.1 to 35% by mass, more preferably from 0.5 to 30% by mass, and even more preferably from 1 to 25% by mass, relative to the solid content of the resist composition.

[0346] 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 "acid labile group" refers to a group that has a leaving group and that is eliminated by contact with an acid to form a hydrophilic group (e.g., a hydroxy group or a carboxy group).

[0347] The resist composition preferably further contains a quencher (hereinafter sometimes referred to as "quencher (C)") and / or a solvent (hereinafter sometimes referred to as "solvent (E)").

[0348] <Acid generator (B)> The acid generator (B) may be either a nonionic compound or an ionic compound. Examples of nonionic compounds include sulfonate esters (e.g., 2-nitrobenzyl ester, aromatic sulfonate, oxime sulfonate, N-sulfonyloxyimide, sulfonyloxyketone, diazonaphthoquinone 4-sulfonate), sulfones (e.g., disulfone, ketosulfone, sulfonyldiazomethane), and the like. Examples of ionic compounds 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, benzenesulfonyl anions, sulfonylimide anions, sulfonylmethide anions, and carboxylate anions.

[0349] 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.

[0350] A preferred embodiment of the acid generator (B) is a salt represented by formula (B1) (hereinafter sometimes referred to as "salt (B1)" or "acid generator (B1)") or a salt represented by formula (B2) (hereinafter sometimes referred to as "salt (B2)" or "acid generator (B2)").

[0351] [ka]

[0352] [In formula (B1), all symbols have the same meanings as defined above.] 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 Examples of such groups include groups that bond to the following:

[0353] The hydrocarbon group preferably has 1 to 48 carbon atoms, more preferably 1 to 42 carbon atoms, even more preferably 1 to 36 carbon atoms, even more preferably 1 to 30 carbon atoms, and even more preferably 1 to 24 carbon atoms.

[0354] Examples of the chain hydrocarbon group include groups in which nb 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, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentanedecyl, and heptadecyl. Examples of the alkenyl group include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl.

[0355] The number of carbon atoms in the chain hydrocarbon group is 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.

[0356] 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.

[0357] 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.

[0358] More specifically, alicyclic hydrocarbon groups represented by the following formulas are included.

[0359] [ka]

[0360] L b1When 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 even more preferably 3 to 8. b1 When the alicyclic hydrocarbon group is a polycyclic cycloalkyl group, the alicyclic hydrocarbon group preferably has 6 to 24 carbon atoms, more preferably 6 to 20 carbon atoms, even more preferably 6 to 18 carbon atoms, even more preferably 6 to 12 carbon atoms, and even more preferably 7 to 12 carbon atoms.

[0361] Examples of aromatic hydrocarbon groups include groups in which nb1 hydrogen atoms have been removed from an aryl group, such as a phenyl group, naphthyl group, anthryl group, biphenyl group, and fluorenyl group.

[0362] More specifically, aromatic hydrocarbon groups represented by the following formulas are included.

[0363] [ka]

[0364] 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.

[0365] 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 an alkyl group is replaced with -CO-), alkylcarbonyloxy groups (in which -CH-CH- at any position in an alkyl group is replaced with -CO-O-), alkanediyloxy groups (in which -CH- at any position in an alkanediyl group is replaced with -O-), alkanediyloxycarbonyl groups (in which -CH-CH- at any position in an alkanediyl group is replaced with -O-CO-), alkanediylcarbonyl groups (in which -CH- at any position in an alkanediyl group is replaced with -CO-), and alkanediylcarbonyloxy groups (in which -CH-CH- at any position in an alkanediyl group is replaced with -CO-). 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] 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.

[0367] [ka]

[0368] 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:

[0369] [ka]

[0370] 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. The group combining an alicyclic hydrocarbon group with an aromatic hydrocarbon group may be a fused ring.

[0371] L b2 Examples of the divalent hydrocarbon group include 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:

[0372] 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.

[0373] 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.

[0374] 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, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, a thiol group, an alkylthio group, or an alkylsulfonyl group.

[0375] 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, respectively, 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.

[0376] Y b1 Examples of the substituent that the methyl group may have include a halogen atom, a cyano group, a hydroxy group, and a nitro group. Y 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 with -O-, -S-, -CO-, or -SO2-.

[0377] 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- in the hydrocarbon group having 1 to 18 carbon atoms that the cyclic hydrocarbon group of may have as a substituent is replaced with -O-, -S-, -CO- or -SO2- include the same groups as those exemplified as the group in which -CH2- in the hydrocarbon group of Lb1 is replaced with -O-, -S-, -CO- or -SO2-, 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.

[0378] 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)").

[0379] [ka]

[0380] [In formula (B1-A1), L b2 and Y b1 has the same meaning as in formula (B1). 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.

[0381] 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. X 1 represents -O-CO-, -CO-O-, -O-CO-O- or -O-.

[0382] 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-.

[0383] 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 b4 Examples of the alkyl group having 1 to 6 carbon atoms 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.

[0384] Q b1 , Q b2 , Q b3 and Q b4Examples of the perfluoroalkyl group having 1 to 6 carbon atoms 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.

[0385] 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.

[0386] 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.

[0387] 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—.

[0388] L b3 As the hydrocarbon group in the formula (B1), within the range permitted by the upper limit of the number of carbon atoms, b1 Examples of the hydrocarbon groups include the same groups as those exemplified above. In formula (B1-A1), L b3is 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 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-.

[0389] [ka]

[0390] [In formula (Lb3-1), nb2 has the same meaning as in formula (B1-A1). 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.

[0391] W b3 represents 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.

[0392] * and ** represent binding sites, * represents X 1 represents the binding site with In formula (Lb3-1), L b31 The chain hydrocarbon group is, as far as the upper limit of the number of carbon atoms allows, L in formula (B1). b1 Examples of the chain hydrocarbon groups include the same groups as those exemplified above.

[0393] In formula (Lb3-1), W b3 The alicyclic hydrocarbon group and aromatic hydrocarbon group are, as far as the upper limit of the number of carbon atoms allows, L in formula (B1). b1 Examples of the alicyclic hydrocarbon groups and aromatic hydrocarbon groups are the same as those exemplified above.

[0394] In formula (Lb3-1), L b31 The substituents which the chain hydrocarbon group of W may have and b3 The substituents that the alicyclic hydrocarbon group and aromatic hydrocarbon group may have are as follows: b1 Examples of the substituent that the hydrocarbon group may have include the same groups as the substituents exemplified above.

[0395] 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-).

[0396] 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 b31 represents a bonding site with L, and ** represents a hydrogen atom, a substituent, or L b2 represents a binding site with at least one ** b2represents 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), carbonate ring, sulfonate ester ring (sultone), or acetal ring is formed.

[0397] [ka]

[0398] 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 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 binding 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.

[0399] 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.

[0400] [ka]

[0401] 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).

[0402] [ka]

[0403] [ka]

[0404] [ka]

[0405] 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.

[0406] 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.

[0407] Preferred anions represented by formula (B1-A1) include anions represented by formulas (B1a-1) to (B1a-70).

[0408] [ka]

[0409] [ka]

[0410] [ka]

[0411] Among these, anions represented by any one 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.

[0412] The anion represented by formula (B1-A2) is represented by the following formula:

[0413] [ka]

[0414] [In formula (B1-A2), L b2 and Y b1 has the same meaning as in formula (B1). 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--.

[0415] 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. 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.

[0416] However, 1≦nb4+nb3≦5 is satisfied. In formula (B1-A2), L b2 As the hydrocarbon group, within the range permitted by the upper limit of the number of carbon atoms, L b2 Examples of the hydrocarbon groups include the same groups as those exemplified in L b2 The substituents that the hydrocarbon group may have are also defined as follows: b2Examples of the substituents that may be contained in the hydrocarbon groups exemplified above include the same groups as those exemplified above.

[0417] 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.

[0418] In formula (B1-A2), Y b1 As the cyclic hydrocarbon group, within the range permitted by the upper limit of the number of carbon atoms, Y b1 The cyclic hydrocarbon groups exemplified by Y b1 The substituents that the methyl group and cyclic hydrocarbon group may have are the same as those exemplified in formula (B1) Y b1 Examples of the substituents include the same groups as those which may be contained in the methyl group and cyclic hydrocarbon group.

[0419] 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 b1Specifically, 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.

[0420] 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 meta position of the benzene ring relative to the bonding position of the above.

[0421] [ka]

[0422] [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.

[0423] R b1 Examples 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.

[0424] 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 -CH2- 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. Specific examples of these are the same as those described above.

[0425] 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.

[0426] nb3 is 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.

[0427] 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.

[0428] [ka]

[0429] Examples of the sulfonylimide anion and sulfonylmethide anion include those represented by the following formulas.

[0430] [ka]

[0431] [In formula (B2), A 1 represents a nitrogen atom or a carbon atom. 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-.

[0432] 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-.

[0433] nb5 represents an integer of 2 or 3. When nb5 is 2, A 1 is a nitrogen atom, and when nb5 is 3, A 1 is a carbon atom. The groups in parentheses may be the same or different, and two groups in parentheses are bonded to form A 1 may form a ring containing:

[0434] Z2 + represents an organic cation. In formula (B2), L b2 ′ and Y b1 Examples of the hydrocarbon group, cyclic hydrocarbon group and substituent of L′ are b2 and Yb1 The same groups as those shown below can be mentioned.

[0435] In formula (B2), 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.

[0436] In formula (B2), Y b1 is 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 more preferably a trifluoromethyl group or a group represented by formulae (Y1) to (Y36) exemplified in formula (B1-A1).

[0437] In formula (B2), two -SO2-L b2 ′-Y b1 ' together to form A 1 When a ring containing the formula (B2′) is formed, examples thereof include anions represented by the formula (B2′).

[0438] [ka]

[0439] [In formula (B2′), A 1 , Y b1 ′, L b2 ' and nb5 have the same meaning as in formula (B2). 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.

[0440] Examples of the anion in the salt represented by formula (B2) include the following: Among these, the anions represented by formula (B3a-1) and formula (B3a-2) are preferred.

[0441] [ka]

[0442] In another embodiment of the acid generator (B), an anion 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). Examples of carboxylate anions include the following: However, the acid generator (B) having a carboxylate anion excludes the carboxylate salt represented by formula (I).

[0443] [ka]

[0444] Z1 + and Z2 +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 or aryl iodonium 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).

[0445] [ka]

[0446] [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.

[0447] 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-.

[0448] 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.

[0449] 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.

[0450] 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-.

[0451] 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.

[0452] 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-.

[0453] 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.

[0454] 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-.

[0455] 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.

[0456] q2 and r2 each independently represent an integer of 0 to 4; u2 represents 0 or 1. 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 b16 are 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.

[0457] 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.

[0458] o21, p22, q23, r24, t25 and s26 each independently represent an integer of 0 to 4. When u3, u4 and u5 each represent 2 or more, the groups in the parentheses are the same or different.

[0459] When o21, p22, q23, r24, t25 and s26 are each 2 or more, multiple R b21 ~R b26 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.

[0460] 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.

[0461] 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.

[0462] 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:

[0463] [ka]

[0464] 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. 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.

[0465] 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.

[0466] 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, a 2-methyl-6-ethylphenyl group, etc.) and aromatic hydrocarbon groups having an alicyclic hydrocarbon group (such as a p-cyclohexylphenyl group, a p-adamantylphenyl group, etc.).

[0467] 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.

[0468] 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.

[0469] 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.

[0470] 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.

[0471] 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.

[0472] 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.

[0473] [ka]

[0474] 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.

[0475] 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.

[0476] 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.

[0477] R b27 ~R b29 Examples of the acid labile group include groups represented by formula (1) or formula (2) exemplified in this specification. Among the cations (b2-1) to (b2-5), the cation (b2-1), the cation (b2-4) or the cation (b2-5) is preferred.

[0478] Examples of the cation (b2-1) include the following cations.

[0479] [ka]

[0480] Examples of the cation (b2-2) include the following cations.

[0481] [ka]

[0482] Examples of the cation (b2-3) include the following cations.

[0483] [ka]

[0484] Examples of the cation (b2-4) include the following cations.

[0485] [ka]

[0486] Examples of the cation (b2-5) include the following cations.

[0487] [ka]

[0488] 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), and (B3a-1) to (B3a-20) with cations (b2-1), (b2-2), (b2-3), (b2-4), and (b2-5).

[0489] 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.

[0490] [ka]

[0491] [ka]

[0492] [ka]

[0493] [ka]

[0494] [ka]

[0495] [ka]

[0496] [ka]

[0497] [ka]

[0498] In the resist composition of the present invention, the content of the acid generator (B) is, relative to the solid content of the resist composition, for example, 0.1 to 99.9% by mass, preferably 1 to 45% by mass, more preferably 1 to 40% by mass, and even more preferably 3 to 35% by mass. Furthermore, when the resist composition contains the resin (A) described below, the content of the acid generator (B) is, relative to 100 parts by mass of the resin (A), preferably 1 to 50 parts by mass, more preferably 1 to 45 parts by mass, even more preferably 3 to 40 parts by mass, and even more preferably 3 to 35 parts by mass.

[0499] In the resist composition of the present invention, when the resin (A) described below is contained, the total content of the carboxylate (I), acid generator (B), etc. is preferably 1 part by mass or more (more preferably 3 parts by mass or more) and preferably 55 parts by mass or less (more preferably 50 parts by mass or less, and even more preferably 45 parts by mass or less) per 100 parts by mass of the resin (A).

[0500] <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)"), structural units other than structural unit (a1) and structural unit (s) (for example, a structural unit having a halogen atom (hereinafter sometimes referred to as "structural unit (a4)") described below, a structural unit having a non-leaving hydrocarbon group (hereinafter sometimes referred to as "structural unit (a5)") described below, and other structural units derived from monomers known in the art.

[0501] <Structural unit (a1)> The structural unit (a1) is derived from a monomer having an acid labile group (hereinafter sometimes referred to as "monomer (a1)").

[0502] 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)).

[0503] [ka]

[0504] [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 Ra1 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.

[0505] ma and na each independently represent 0 or 1, and at least one of ma and na represents 1. * denotes a binding site.]

[0506] [ka]

[0507] [In formula (2), R a1 ′ and R a2 R ′ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms; 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.

[0508] 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.

[0509] R a1 , R a2 and R a3Examples of the alkenyl group in the formula (I) include ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, hexenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups.

[0510] 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.

[0511] [ka]

[0512] 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. 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.

[0513] 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-.

[0514] [ka]

[0515] R a1 ′, R a2 ′ and R a3 Examples of the hydrocarbon group in "" include alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these groups.

[0516] Alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by 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 X and X′ are bonded to each other to form a heterocyclic group together with the carbon atoms to which they are bonded, -C(R a1 ′)(R a2 ′)-XR a3 Examples of ' include the following groups: * represents a binding site.

[0517] [ka]

[0518] R a1 , R a2 , R a3 , R a1 , R a2 ′ and R a3 The halogen atom that may be contained in "" includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R a1 ′ and R a2 At least one of the ' is preferably a hydrogen atom.

[0519] na' is preferably 0. Examples of the group (1) include the following groups. 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.

[0520] 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. 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.

[0521] Specific examples of the group (1) include the following: * represents a binding site.

[0522] [ka]

[0523] [ka]

[0524] Specific examples of group (2) include the following groups: * represents a binding site.

[0525] [ka]

[0526] 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. 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.

[0527] 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.

[0528] [ka]

[0529] [In formulas (a1-0), (a1-1) and (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.

[0530] 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.

[0531] 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 1 to 4, more preferably 1), and more preferably an oxygen atom.

[0532] 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.

[0533] 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.

[0534] 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.

[0535] 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.

[0536] 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.

[0537] 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.

[0538] 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.

[0539] 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.

[0540] 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.

[0541] 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.

[0542] 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.

[0543] [ka]

[0544] 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.

[0545] [ka]

[0546] 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.

[0547] [ka]

[0548] 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%.

[0549] 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. Also, the content can 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, the content can be 5 to 80 mol%, preferably 5 to 75 mol%, and more preferably 10 to 70 mol%.

[0550] When the resin (A) contains 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 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, the total content can be 10 to 95 mol%, preferably 15 to 85 mol%, more preferably 15 to 80 mol%, even more preferably 20 to 80 mol%, and even more preferably 20 to 75 mol%.

[0551] 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)").

[0552] [ka]

[0553] [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.

[0554] 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.

[0555] 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

[0556] 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-.

[0557] 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.

[0558] mc represents an integer between 0 and 2. R a1 and R a17 Examples of the halogen atom in the formula include a fluorine atom, a chlorine atom, and a bromine atom.

[0559] R a1 and R a17Examples 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, still more preferably a methyl group or an ethyl group, and even more preferably a methyl group.

[0560] 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 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 a methoxy group or an ethoxy group, and even more preferably a methoxy group.

[0561] 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 may be an alkoxyalkyl group having 2 to 8 carbon atoms, preferably an alkoxyalkyl group having 2 to 4 carbon atoms, more preferably a methoxymethyl group or an ethoxyethyl group, and even more preferably a methoxymethyl group.

[0562] R a17Examples 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 may be an alkoxyalkoxy group having 2 to 8 carbon atoms, preferably an alkoxyalkoxy group having 2 to 4 carbon atoms, and more preferably a methoxyethoxy group or an ethoxyethoxy group.

[0563] 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 may be an alkylcarbonyl group having 2 to 4 carbon atoms, preferably an alkylcarbonyl group having 2 to 3 carbon atoms, and more preferably an acetyl group.

[0564] R a17 Examples of the alkylcarbonyloxy group in the formula (I) include an acetyloxy group, a propionyloxy group, and a butyryloxy group. The alkylcarbonyloxy group may be an alkylcarbonyloxy group having 2 to 4 carbon atoms, preferably an alkylcarbonyloxy group having 2 to 3 carbon atoms, and more preferably an acetyloxy group.

[0565] 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.

[0566] A a11Examples 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.

[0567] R a18 Examples 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.

[0568] 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 a methyl group is replaced with -NRa18 -), 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- at any position in an alkyl group is replaced with -NR a18 -), peptide group (-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.

[0569] Examples of the alkylamino group include alkylamino groups having 1 to 11 carbon atoms, such as methylamino, ethylamino, propylamino, butylamino, pentylamino, hexylamino, and octylamino. The number of carbon atoms in the alkylamino group is preferably 1 to 8, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3.

[0570] Examples of the alkanediylamino group include alkanediylamino groups having 1 to 11 carbon atoms, such as a methyleneamino group, an ethyleneamino group, a propyleneamino group, etc. The number of carbon atoms in the alkanediylamino group is preferably 1 to 8, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3.

[0571] 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, a11 Examples of the alkanediyl groups include the same alkanediyl groups as those shown in the above.

[0572] 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.

[0573] 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.

[0574] 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.

[0575] 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):

[0576] [ka]

[0577] 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. 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 groups.

[0578] R a35 and R a36 Examples of the divalent 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

[0579] [ka]

[0580] 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.

[0581] 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.

[0582] -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.

[0583] -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.

[0584] 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).

[0585] [ka]

[0586] 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. The content 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, 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 even more preferably 20 to 60 mol%.

[0587] 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)").

[0588] [ka]

[0589] [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.

[0590] 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-.

[0591] s1 represents an integer of 1 to 3. s1′ represents an integer of 0 to 3. R a8 Examples of the halogen atom in include a fluorine atom, an iodine atom, a chlorine atom, and a bromine atom. Of these, a fluorine atom is preferred.

[0592] 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.

[0593] In formula (a1-5), R a8is preferably a hydrogen atom, a methyl group or a trifluoromethyl group. L 51 is preferably an oxygen atom.

[0594] 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.

[0595] Z a1 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.

[0596] [ka]

[0597] 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%.

[0598] 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)").

[0599] [ka]

[0600] [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.

[0601] 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.

[0602] X a61 is a single bond, -CO-O-* or -CO-NR 5 -*, * represents the bonding site with -Ar, R 5 represents a hydrogen atom or an alkyl group having 1 to 4 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.

[0603] Ar represents an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent.] R a61 Examples of the halogen atom in include a fluorine atom, an iodine atom, a chlorine atom, and a bromine atom. Of these, a fluorine atom is preferred.

[0604] 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.

[0605] 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 pentyl 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.

[0606] 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.

[0607] 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.

[0608] 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.

[0609] [ka]

[0610] 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.

[0611] 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.

[0612] X a62is 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 represented by Ar include a phenylene group, a naphthylene group, an anthrylene group, a biphenylene group, and a phenanthrylene group.

[0613] 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.

[0614] 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.

[0615] 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.

[0616] 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.

[0617] 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.

[0618] 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.

[0619] 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.

[0620] 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.

[0621] 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), more preferably structural units represented by formulas (a1-6-1), (a1-6-2), (a1-6-4), (a1-6-5), (a1-6-7) or (a1-6-8), and even more preferably structural units represented by formulas (a1-6-1) or (a1-6-2).

[0622] [ka]

[0623] [ka]

[0624] In the structural units represented by formulas (a1-6-1) to (a1-6-9), (a1-6-16) to (a1-6-21), (a1-6-28) to (a1-6-30), and (a1-6-37) to (a1-6-44), R a61 In the structural units represented by formulae (a1-6-10) to (a1-6-15), (a1-6-22) to (a1-6-27), and (a1-6-31) to (a1-6-36), R a61 The structural unit (a1-6) also includes 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 the like.

[0625] 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 65 mol%.

[0626] Further, examples of the structural unit (a1) include the following structural units.

[0627] [ka]

[0628] When resin (A) contains structural units represented by formulae (a1-7-1) to (a1-7-7), the content of these structural units relative to the total structural units of resin (A) 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. Also, the content may 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%.

[0629] Further, examples of the structural unit (a1) include the following structural units.

[0630] [ka]

[0631] When resin (A) contains structural units represented by formulae (a1-8-1) to (a1-8-3), the content of these structural units relative to the total structural units of resin (A) 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. Also, the content may 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%.

[0632] <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.

[0633] 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)"), and structural units that decompose upon exposure to generate acid (hereinafter sometimes referred to as "structural unit (a7)").

[0634] <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.

[0635] [ka]

[0636] [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.

[0637] 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

[0638] R a28 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. L a21represents 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-.

[0639] 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-.

[0640] 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.

[0641] 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.

[0642] 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.

[0643] 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, and a tert-butyl 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.

[0644] A a21 -CH2- in the alkanediyl group is -O-, -CO- or -NR a28 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 a methyl group is replaced with -NRa28 -), 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- at any position in an alkyl group is replaced with -NR a28 -), peptide group (-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 a28 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.

[0645] Among them, 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.

[0646] 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.

[0647] L a21 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).

[0648] 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.

[0649] 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.

[0650] 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.

[0651] Examples of the alkanpentyl group include a methanepentyl group, an ethanepentyl group, a propanepentyl group, a butanepentyl group, a pentanepentyl group, and a hexanepentyl group.

[0652] 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.

[0653] 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.

[0654] [ka]

[0655] 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.

[0656] 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.

[0657] 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.

[0658] L a21Examples 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.

[0659] 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.

[0660] Further examples include groups in which one or more hydrogen atoms of the above groups are replaced with bonding sites. The aromatic hydrocarbon group preferably has 6 to 20 carbon atoms, more preferably 6 to 18 carbon atoms, even more preferably 6 to 14 carbon atoms, still more preferably 6 to 12 carbon atoms, and even more preferably 6 to 10 carbon atoms.

[0661] 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

[0662] 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.

[0663] 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.

[0664] 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.

[0665] 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.

[0666] 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.

[0667] 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.

[0668] 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.

[0669] 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.

[0670] 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.

[0671] 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.

[0672] 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.

[0673] [ka]

[0674] 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.

[0675] [ka]

[0676] 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.

[0677] 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.

[0678] 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.

[0679] L a21 The hydrocarbon group of the formula (I) is replaced by -O- or -CO-. a21 may substantially have a substituent such as a hydroxy group, a carboxy group, an alkoxy group, a thiol group, a sulfonyl group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkoxyalkyl group, an alkoxyalkoxy group, an acryloyloxy group, or a methacryloyloxy group. The number of carbon atoms in the alkoxy group is preferably 1 to 12, more preferably 1 to 6, even more preferably 1 to 4, and still more preferably 1 to 3. The number of carbon atoms in the alkoxycarbonyl group, alkylcarbonyl group, or alkylcarbonyloxy group is preferably 2 to 12, more preferably 2 to 6, even more preferably 2 to 4, and still more preferably 2 to 3. The number of carbon atoms in the alkoxyalkyl group or alkoxyalkoxy group is preferably 2 to 12, more preferably 2 to 8, even more preferably 2 to 6, and still more preferably 2 to 4.

[0680] The above groups also include the same groups as those exemplified in this specification. L a21The 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.

[0681] 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

[0682] L a21is 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-).

[0683] L a22Examples 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. Examples of branched alkanediyl groups include ethane-1,1-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-2,2-diyl, 1-methylpropane-1,3-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, 1-dimethylpropane-1,3-diyl, pentane-2,4-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl. 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.

[0684] Examples of the chain hydrocarbon group in which -CH2- is replaced with -O- or -CO- include the same groups as those exemplified in this specification. L a22 may have one or more fluorine atoms.

[0685] 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 units shown below.

[0686] [ka]

[0687] 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 (a2-1) described below. The structural unit (a2) may contain one type alone or two or more types.

[0688] 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)").

[0689] [ka]

[0690] [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.

[0691] 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.

[0692] A a21represents 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

[0693] 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. When nA2 is 2 or greater, the groups in the parentheses may be the same or different.

[0694] na21 represents an integer of 0 to 4. 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. R a2 and A a21 The groups include the same groups as those exemplified in formula (a2).

[0695] R a27 Examples of the halogen atom include a fluorine atom, a chlorine atom, an iodine atom, and a bromine atom. R a27 Examples of the alkyl group having 1 to 6 carbon atoms and optionally having 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 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.

[0696] 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, still more preferably a methoxy group or an ethoxy group, and still more preferably a methoxy group.

[0697] 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 a methoxymethyl group or an ethoxyethyl group, and even more preferably a methoxymethyl group.

[0698] 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, and more preferably a methoxyethoxy group or an ethoxyethoxy group.

[0699] 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 3 carbon atoms, and more preferably an acetyl group.

[0700] 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 3 carbon atoms, and more preferably an acetyloxy group.

[0701] 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.

[0702] 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.

[0703] 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.

[0704] 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) includes structural units represented by formulae (a2-2-1) to (a2-2-32), (a2-3-1) to (a2-3-24), and structural units represented by formulae (a2-2-1) to (a2-2-32), (a2-3-1) to (a2-3-24), where 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.

[0705] [ka]

[0706] [ka]

[0707] 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 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%.

[0708] 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 a2The 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 incorporate the structural unit into the resin (A). Alternatively, the structural unit (a2-A) can be polymerized using acetoxystyrene or the like, followed by treatment with an alkali such as tetramethylammonium hydroxide, to incorporate the structural unit into the resin (A).

[0709] In the structural unit (a2), L a21 is 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)").

[0710] [ka]

[0711] [In formula (a2-B) and formula (a2-C), R a2 has the same meaning as formula (a2). R a27 has the same meaning as formula (a2-A).

[0712] 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—. X a2 represents a single bond or -CO-.

[0713] R a25 and R a26 each independently represents a hydrogen atom, a methyl group, or a hydroxy group. 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.

[0714] 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. nC22 represents an integer of 0 to 10. When nC22 is 2 or more, a plurality of R a27 may be the same or different from each other. L a25 is preferably -O-, -O-(CH2) f1 It is —CO—O— (wherein f1 represents an integer of 1 to 4), and more preferably —O—.

[0715] R a2 is preferably a methyl group. X a2 is preferably a single bond. R a25 is preferably a hydrogen atom.

[0716] 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.

[0717] 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.

[0718] nC22 is preferably an integer of 0 to 6, more preferably an integer of 0 to 3, and even more preferably 0 or 1. 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.

[0719] [ka]

[0720] 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%.

[0721] [ka]

[0722] [In formula (a2-D), R a2 and A a21 have the same meaning as in formula (a2). R a27 has the same meaning as formula (a2-A).

[0723] R a21 and R a22 each independently represents a fluorinated alkyl group having 1 to 4 carbon atoms. L a24 represents a single bond or an alkanediyl group having 1 to 3 carbon atoms, and the alkanediyl group may be substituted with a fluorine atom.

[0724] 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 from each other.

[0725] However, 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.

[0726] 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.

[0727] L a24 is preferably a single bond or a methylene group. R a27is 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.

[0728] 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.

[0729] 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, sometimes referred to as "structural unit (a2-D1)").

[0730] [ka]

[0731] [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.

[0732] A a21 is preferably a single bond. Examples of the structural unit (a2-D) include the structural units shown below.

[0733] [ka]

[0734] 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 a2 Specific 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.

[0735] 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%.

[0736] <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)).

[0737] 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.

[0738] [ka]

[0739] [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).

[0740] 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-.

[0741] 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.

[0742] X a3 represents -CH2- or an oxygen atom. R a21 represents an aliphatic hydrocarbon group having 1 to 4 carbon atoms. R a22 , Ra23 and R a25 each independently represents a carboxy group, a cyano group, or an aliphatic hydrocarbon group having 1 to 4 carbon atoms.

[0743] p1 represents an integer of 0 to 5. q1 represents an integer of 0 to 3. r1 represents an integer of 0 to 3.

[0744] w1 represents an integer of 0 to 8. When p1, q1, r1 and / or w1 are 2 or more, multiple R a21 , 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.

[0745] 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.

[0746] R a18 , R a19 , R a20 and R a24Examples 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.

[0747] L a8 and L a9 Examples 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.

[0748] 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.

[0749] R a18 ~R a21 is preferably a methyl group. R a22 and R a23 are each independently preferably a carboxy group, a cyano group, or a methyl group.

[0750] p1, q1 and r1 each independently represent an integer of preferably 0 to 2, and more preferably 0 or 1. In formula (a3-4), R a24is 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.

[0751] R a25 is preferably a carboxy group, a cyano group or a methyl group. 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—.

[0752] w1 is preferably an integer of 0 to 2, and more preferably 0 or 1. In particular, the formula (a3-4) is preferably the formula (a3-4)'.

[0753] [ka]

[0754] (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.

[0755] [ka]

[0756] 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%.

[0757] 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%.

[0758] <Structural unit (a4)> The structural unit represented by formula (a4) is shown below.

[0759] [ka]

[0760] [In formula (a4), R 41 represents a hydrogen atom or a methyl group. R 42 represents a saturated hydrocarbon group having 1 to 24 carbon atoms and containing a halogen atom, and -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-.] R 42 Examples of the saturated hydrocarbon group represented by the formula (I) include linear or branched chain saturated hydrocarbon groups, monocyclic or polycyclic alicyclic saturated hydrocarbon groups, and groups formed by combining these groups.

[0761] Examples of the chain saturated 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.

[0762] Examples of the monocyclic or polycyclic alicyclic saturated hydrocarbon group include monocyclic alicyclic saturated 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 saturated 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):

[0763] [ka]

[0764] Examples of groups formed by this combination include groups formed by combining one or more alkyl groups or one or more alkanediyl groups with one or more alicyclic saturated hydrocarbon groups, such as -alkanediyl group-alicyclic saturated hydrocarbon group, -alicyclic saturated hydrocarbon group-alkyl group, and -alkanediyl group-alicyclic saturated hydrocarbon group-alkyl group.

[0765] 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.

[0766] R 42 Examples of the halogen atom contained in the saturated hydrocarbon group include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R 42Examples of saturated hydrocarbon groups in which -CH2- is replaced by -O- 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 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-), and an alkylcarbonyl group (a group in which -CH2- at any position in an alkyl group is replaced by -CO-). ), alkylcarbonyloxy groups (groups in which -CH-CH- at any position in an alkyl group is replaced with -CO-O-), alkanediyloxy groups (groups in which -CH- at any position in an alkanediyl group is replaced with -O-), alkanediyloxycarbonyl groups (groups in which -CH-CH- at any position in an alkanediyl group is replaced with -O-CO-), alkanediylcarbonyl groups (groups in which -CH- at any position in an alkanediyl group is replaced with -CO-), alkanediylcarbonyloxy groups (groups in which -CH- at any position in an alkanediyl group is replaced with -CO-), cycloalkoxy groups, cycloalkylalkoxy groups, and groups 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.

[0767] The structural unit (a4) is R 42 is preferably a saturated hydrocarbon group having a fluorine atom, and R 42However, examples of the structural unit (a4) that is a saturated hydrocarbon group having a fluorine atom include a structural unit represented by formula (a4-1) (hereinafter, sometimes referred to as "structural unit (a4-1)"), a structural unit represented by formula (a4-2) (hereinafter, sometimes referred to as "structural unit (a4-2)"), and a structural unit represented by formula (a4-3) (hereinafter, sometimes referred to as "structural unit (a4-3)").

[0768] The structural unit represented by formula (a4-1) is a structural unit shown below.

[0769] [ka]

[0770] [In formula (a4-1), R 41 represents a hydrogen atom or a methyl group. L 41 represents a single bond or an alkanediyl group having 1 to 4 carbon atoms.

[0771] 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. 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.

[0772] L 42fExamples 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.

[0773] 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.

[0774] L 42fThe 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.

[0775] L 42f 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.

[0776] 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.

[0777] 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.

[0778] 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.

[0779] 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.

[0780] [ka]

[0781] The structural unit represented by formula (a4-2) is a structural unit shown below.

[0782] [ka]

[0783] [In formula (a4-2), R 41 represents a hydrogen atom or a methyl group. L 43f represents a saturated hydrocarbon group having 1 to 20 carbon atoms which may contain a fluorine atom, and -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-.

[0784] R 43f represents a saturated hydrocarbon group having 1 to 20 carbon atoms which may contain a fluorine atom, and -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-. 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 saturated hydrocarbon group in L include linear or branched chain saturated hydrocarbon groups, monocyclic or polycyclic alicyclic saturated hydrocarbon groups, and groups formed by combining these groups. 43f and R 43f Examples of saturated hydrocarbon groups in 43f and R 43f As long as the upper limit of the total number of carbon atoms in 42 Examples of the saturated hydrocarbon group include the same groups as the exemplified saturated hydrocarbon groups.

[0785] L 43f The saturated hydrocarbon group is preferably an alkanediyl group having 1 to 6 carbon atoms or a group represented by the formula (L43f-1).

[0786] [ka]

[0787] [In formula (L43f-1), s represents 0 or 1. L 45f and L 46f each independently represents a divalent saturated hydrocarbon group having 1 to 5 carbon atoms which may contain a fluorine atom.

[0788] L 47f represents a single bond or a divalent saturated hydrocarbon group having 1 to 5 carbon atoms which may contain a fluorine atom. X 46f and X 47f each independently represents -O-, -CO-, -CO-O- or -O-CO-.

[0789] However, L 45f , L 46f , L 47f , X 46f and X 47f The total number of carbon atoms is 7 or less. * and ** are binding sites, and ** is -O-CO-R 43f] L in the group represented by formula (L43f-1) 45f , L 46f and L 47f Examples of the divalent saturated hydrocarbon group represented by include a linear or branched alkanediyl group, a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, and a divalent saturated hydrocarbon group formed by combining an alkanediyl group with a divalent alicyclic saturated 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.

[0790] 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

[0791] [ka]

[0792] R 43f is preferably a saturated 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).

[0793] [ka]

[0794] [In formula (a4-2A) and formula (a4-2B), R 41 and L 43f represents the same as in formula (a4-2). R 43fArepresents a saturated hydrocarbon group having 1 to 20 carbon atoms and containing a fluorine atom.

[0795] A 43f represents a divalent saturated hydrocarbon group having 1 to 17 carbon atoms which may have a fluorine atom, and -CH2- contained in the saturated hydrocarbon group may be replaced with -O- or -CO-.

[0796] X 43 represents **-O-CO- or **-CO-O-, and ** represents A 43f represents the binding site with R 43fB represents a saturated hydrocarbon group having 1 to 17 carbon atoms which may contain a fluorine atom.

[0797] 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 saturated hydrocarbon group of R 42 Examples of the saturated hydrocarbon groups inclu...

Claims

1. A carboxylic acid generator comprising a carboxylate represented by formula (I): 【Chemistry 1】 [In formula (I), X represents a sulfur atom or an iodine atom. m10 represents 0 or 1, and when X is a sulfur atom, m10 is 1, and when X is an iodine atom, m10 is 0. R １Ａ and R １Ｂ are each independently *-X １ -R １０ Or *-X １ -L １０ -X ２ -R １０ represents R ４ is bonded to a benzene ring or R ７ represents the bonding site with the benzene ring to which it is attached. X １ and X ２ are each independently *-CO-O-, *-O-CO-, *-O-CO-O- or *-O- (wherein * represents a benzene ring or L １０ represents a binding site with １０ represents a hydrocarbon group having 1 to 28 carbon atoms which may have a substituent, and the —CH ２ - is -O-, -S-, -SO ２ It may be replaced by --or --CO--. R １０ is -SO ２ Represents a group having -. R ４ represents a halogen atom or a hydrocarbon group having 1 to 36 carbon atoms, the hydrocarbon group optionally having a substituent, and the —CH ２ - is -O-, -S-, -CO-, -SO- or -SO ２ It may be replaced with -. R ７ , R ８ and R ９ each independently represents a halogen atom or a hydrocarbon group having 1 to 36 carbon atoms, the hydrocarbon group optionally having a substituent, ２ - is -O-, -S-, -CO-, -SO- or -SO ２ When X is a sulfur atom, R ７ and R ８ Or R ８ and R ９ is bonded to S ＋ The R forming the ring may form a ring containing ７ and R ８ Or R ８ and R ９ , S ＋ The —CH ２ - is -O-, -S-, -CO-, -SO- or -SO ２ It may be replaced with -. m1A represents an integer of 0 to 5, and when m1A is 2 or more, a plurality of R １Ａ may be the same or different from each other. m1B represents an integer of 0 to 4, and when m1B is 2 or more, a plurality of R １Ｂ may be the same or different, provided that either m1A or m1B is an integer of at least 1. m4 represents an integer of 0 to 5, and when m4 is 2 or more, a plurality of R ４ may be the same or different, and satisfy 0≦m1A+m4≦5. m7 represents an integer of 0 to 4, and when m7 is 2 or more, a plurality of R ７ may be the same or different, and satisfy 0≦m1B+m7≦4. m8 represents an integer of 0 to 5, and when m8 is 2 or more, a plurality of R ８ may be the same or different from each other. m9 represents an integer of 0 to 5, and when m9 is 2 or more, a plurality of R ９ may be the same or different from each other. X ０ represents a hydrocarbon group having 2 to 72 carbon atoms which may have a substituent, and the —CH ２ - is -O-, -S-, -CO- or -SO ２ - may be replaced.

2. R １０ NO-SO ２ The carboxylic acid generator according to claim 1, wherein the group having - is a group having a ring represented by formula (T1A). 【Chemistry 2】 [In formula (T1A), X １Ａ represents an oxygen atom, a sulfur atom, -NH-, or a methylene group. R ４１Ａ represents 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. ma represents an integer of 0 to 9. When ma is 2 or more, multiple R ４１Ａ may be the same or different. The binding site is at any position.]

3. m1A is an integer of 1 to 3, R １Ａ But -O-CO-OR １０ Or -O-L １０ -C-O-R １０ The carboxylic acid generator according to claim 1,

4. X ０ but, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, an aromatic hydrocarbon group having 6 to 36 carbon atoms, or a group comprising a combination of a chain hydrocarbon group having 1 to 18 carbon atoms and an alicyclic hydrocarbon group having 3 to 36 carbon atoms or an aromatic hydrocarbon group having 6 to 36 carbon atoms, The alicyclic hydrocarbon group, the chain hydrocarbon group and the aromatic hydrocarbon group may have a fluorine atom, an iodine atom, a fluorinated alkyl group having 1 to 4 carbon atoms or a hydroxy group. ２ - is -O-, -S-, -CO- or -SO ２ The carboxylic acid generator according to claim 1, wherein - may be replaced by .

5. X ０ The carboxylic acid generator according to claim 1 , wherein is a group represented by formula (aa): 【Chemistry 3】 [In formula (aa), X ａ and X ｂ each independently represents --O-- or --S--. X １ａ represents a hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and the —CH ２ - is -O-, -S-, -CO- or -SO ２ It may be replaced with -. X ２ａ represents a hydrocarbon group having 1 to 48 carbon atoms which may have a substituent, and the —CH ２ - is -O-, -S-, -CO- or -SO ２ It may be replaced with -. * indicates -COO － represents the bonding site with the carbon atom of

6. X ０ 2. The carboxylic acid generator according to claim 1, wherein is a phenyl group which may have a fluorine atom, an iodine atom, a fluorinated alkyl group having 1 to 4 carbon atoms or a hydroxy group.

7. 7. A resist composition comprising the carboxylic acid generator according to claim 1 and an acid generator other than said carboxylic acid generator.

8. Further comprising a resin including a structural unit having an acid labile group, The resist composition according to claim 7, 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 combination thereof, 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 have 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. 【Chemistry 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 the —CH ２ - is -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 the -CH 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. 【Chemistry 6】 [In formula (a1-5), R ａ８ represents an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, 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. 【Chemistry 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, together with the carbon atoms to which they are attached, a ring having 3 to 20 carbon atoms. X ａ６１ is a single bond, -CO-O-* or -CO-NR ５ - represents *, * represents a bonding site with Ar, R ５ represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. X ａ６２ is a single bond, *-O-L ａ６１ - or *-CO-OL 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.

9. The resist composition according to claim 7, further comprising a resin containing a structural unit represented by formula (a2-A). 【Chemistry 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 the —CH ２ - is -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. 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. 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.

10. 8. The resist composition according to claim 7, wherein the acid generator comprises a salt represented by formula (B1). 【Chemistry 9】 [In formula (B1), L ｂ１ represents a single bond or a (nb1+1)-valent hydrocarbon group which may have a substituent, and —CH ２ - is -O-, -S-, -CO- or -SO ２ It may be replaced with -. L ｂ２ represents a single bond or a divalent hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and the —CH ２ - is -O-, -S-, -CO- or -SO ２ It may be replaced with -. Y ｂ１ represents a methyl group which may have a substituent or a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and —CH ２ - is -O-, -S-, -SO ２ It may be replaced by --or --CO--. 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.

11. (1) A step of applying the resist composition according to claim 7 onto a substrate; (2) A step of 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:

12. A carboxylate represented by formula (I): 【Chemistry 10】 [In formula (I), X represents a sulfur atom or an iodine atom. m10 represents 0 or 1, and when X is a sulfur atom, m10 is 1, and when X is an iodine atom, m10 is 0. R １Ａ and R １Ｂ are each independently *-X １ -R １０ Or *-X １ -L １０ -X ２ -R １０ represents R ４ is bonded to a benzene ring or R ７ represents the bonding site with the benzene ring to which it is attached. X １ and X ２ are each independently *-CO-O-, *-O-CO-, *-O-CO-O- or *-O- (wherein * represents a benzene ring or L １０ represents a binding site with １０ represents a hydrocarbon group having 1 to 28 carbon atoms which may have a substituent, and the —CH ２ - is -O-, -S-, -SO ２ It may be replaced by --or --CO--. R １０ is -SO ２ Represents a group having -. R ４ represents a halogen atom or a hydrocarbon group having 1 to 36 carbon atoms, the hydrocarbon group optionally having a substituent, and the —CH ２ - is -O-, -S-, -CO-, -SO- or -SO ２ It may be replaced with -. R ７ , R ８ and R ９ each independently represents a halogen atom or a hydrocarbon group having 1 to 36 carbon atoms, the hydrocarbon group optionally having a substituent, ２ - is -O-, -S-, -CO-, -SO- or -SO ２ When X is a sulfur atom, R ７ and R ８ Or R ８ and R ９ is bonded to S ＋ The R forming the ring may form a ring containing ７ and R ８ Or R ８ and R ９ , S ＋ The —CH ２ - is -O-, -S-, -CO-, -SO- or -SO ２ It may be replaced by -. m1A represents an integer of 0 to 5, and when m1A is 2 or more, a plurality of R １Ａ may be the same or different from each other. m1B represents an integer of 0 to 4, and when m1B is 2 or more, a plurality of R １Ｂ may be the same or different, provided that either m1A or m1B is an integer of at least 1. m4 represents an integer of 0 to 5, and when m4 is 2 or more, a plurality of R ４ may be the same or different, and satisfy 0≦m1A+m4≦5. m7 represents an integer of 0 to 4, and when m7 is 2 or more, a plurality of R ７ may be the same or different, and satisfy 0≦m1B+m7≦4. m8 represents an integer of 0 to 5, and when m8 is 2 or more, a plurality of R ８ may be the same or different from each other. m9 represents an integer of 0 to 5, and when m9 is 2 or more, a plurality of R ９ may be the same or different from each other. X ０ represents a hydrocarbon group having 2 to 72 carbon atoms which may have a substituent, and the —CH ２ - is -O-, -S-, -CO- or -SO ２ - may be replaced.

13. R １０ NO-SO ２ The carboxylate according to claim 12, wherein the group having - is a group having a ring represented by formula (T1A). 【Chemistry 11】 [In formula (T1A), X １Ａ represents an oxygen atom, a sulfur atom, -NH-, or a methylene group. R ４１Ａ represents 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. ma represents an integer of 0 to 9. When ma is 2 or more, multiple R ４１Ａ may be the same or different. The binding site is at any position.]

14. m1A is an integer of 1 to 3, R １Ａ But -O-CO-OR １０ Or -O-L １０ -C-O-R １０ The carboxylate according to claim 12 or 13,

15. X ０ but, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, an aromatic hydrocarbon group having 6 to 36 carbon atoms, or a group comprising a combination of a chain hydrocarbon group having 1 to 18 carbon atoms and an alicyclic hydrocarbon group having 3 to 36 carbon atoms or an aromatic hydrocarbon group having 6 to 36 carbon atoms, The alicyclic hydrocarbon group, the chain hydrocarbon group and the aromatic hydrocarbon group may have a fluorine atom, an iodine atom, a fluorinated alkyl group having 1 to 4 carbon atoms or a hydroxy group. ２ - is -O-, -S-, -CO- or -SO ２ The carboxylate according to claim 12 or 13, which may be replaced by -.

16. X ０ The carboxylate according to claim 12 or 13, wherein is a group represented by formula (aa): 【Chemistry 12】 [In formula (aa), X ａ and X ｂ each independently represents --O-- or --S--. X １ａ represents a hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and the —CH ２ - is -O-, -S-, -CO- or -SO ２ It may be replaced with -. X ２ａ represents a hydrocarbon group having 1 to 48 carbon atoms which may have a substituent, and the —CH ２ - is -O-, -S-, -CO- or -SO ２ It may be replaced with -. * indicates -COO － represents the bonding site with the carbon atom of

17. X ０ The carboxylate according to claim 12 or 13, wherein is a phenyl group which may have a fluorine atom, an iodine atom, a fluorinated alkyl group having 1 to 4 carbon atoms, or a hydroxy group.

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