Resist composition and method for producing resist pattern

Abstract

To form a resist pattern having a good pattern collapse margin (PCM).SOLUTION: A resist composition contains a resin containing a structural unit represented by formula (I) and a structural unit having a group represented by formula (II-x).SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a resist composition and a method for manufacturing a resist pattern using the resist composition, etc.

Background Art

[0002] Patent Document 1 describes a resist composition containing a resin including the following structural unit.

[0003]

Chemical Formula

[0004] Patent Document 2 describes a resist composition containing a resin including the following structural unit.

[0005]

Chemical Formula

Prior Art Documents

Patent Documents

[0006]

Patent Document 1

Patent Document 2

Summary of the Invention

Problems to be Solved by the Invention

[0007] There is a need for a technique capable of forming a resist pattern with good pattern collapse resistance (PCM).

Means for Solving the Problems

[0008] The present invention includes the following inventions. [Invention 1] A resist composition containing a resin having a structural unit represented by formula (I) and a structural unit having a group represented by formula (II-x).

[0009]

Chemical formula

[0010] [In formula (I), X 0 represents a single bond or a hydrocarbon group having 1 to 72 carbon atoms which may have a substituent, and -CH 2 - contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -.

[0011] L 10 represents a single bond or a hydrocarbon group having 1 to 36 carbon atoms which may have a substituent, and -CH 2 - contained in the hydrocarbon group may be replaced by -O-, -S-, -SO 2 - or -CO-.

[0012] R 10 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. X 10 represents a single bond, *-O-*, *-CO-O-*, *-O-CO-O-*, *-CO-NR 9 -*, *-NR 9 -CO-O-*, *-O-CO-NR 9 -* or *-Ax-Ph-Ay-*.

[0013] R 9 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ph represents a phenylene group which may have a substituent. Ax and Ay each independently represent one or more bond types selected from the group consisting of a single bond, an ether bond, a thioether bond, an amide bond, an ester bond or a carbonate ester bond.

[0014] * and ** represent binding sites, and * represents the binding site with the carbon atom to which R 10 is attached. R 3 ,R 4 ,R 5 and R 6 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH 2 - in the hydrocarbon group may be replaced by -O-, -S-, -NR 7 -, -SO 2 - or -CO-, and R 3 and R 4 ,R 5 and R 6 or R 3 and R 4 and R 5 may each be bonded to form a cyclic hydrocarbon group having 3 to 20 carbon atoms. The cyclic hydrocarbon group may have a double bond between one or more adjacent carbon atoms, and -CH 2 - in the cyclic hydrocarbon group may be replaced by -O-, -CO- or -NR 7 -, and -CH= in the cyclic hydrocarbon group may be replaced by -N=.

[0015] R 7 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH 2 - in the hydrocarbon group may be replaced by -O-, -S-, -SO 2 - or -CO-.]

[0016]

Chemical formula

[0017] [In formula (II-x), ring W 1 represents a heterocyclic ring having 2 to 36 carbon atoms. The hydrogen atoms contained in the heterocyclic ring may be substituted with halogen atoms or hydrocarbon groups having 1 to 24 carbon atoms, and -CH 2- may be replaced by an -O-, -S-, -CO- or -NR c - group.

[0018] R c represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. * represents a bonding site. [Invention 2] X 10 is a single bond or a group represented by any one of formula (X 10 -1) to formula (X 10 -10) in the resist composition according to [Invention 1].

[0019] [Chemical formula]

[0020] [In formula (X 10 -1) to formula (X 10 -10), *, ** are bonding sites, and * represents the bonding site with the carbon atom to which R 10 is bonded. Rx represents a halogen atom, a hydroxy group, a fluorinated alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 18 carbon atoms or an alkoxy group having 1 to 6 carbon atoms.

[0021] mx represents any integer from 0 to 4. X 20 represents -O- or -NR 9 -. R 9 represents the same meaning as in formula (I). [Invention 3] L 10 is a single bond, a chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent (provided that -CH 2 - contained in the chain hydrocarbon group may be replaced by -O- or -CO-), a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent (provided that -CH 2 - contained in the cyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2- may be replaced therewith. ) or a group formed by combining an optionally substituted aliphatic hydrocarbon group having 1 to 8 carbon atoms and an optionally substituted cyclic hydrocarbon group having 3 to 24 carbon atoms (provided that -CH 2 - contained in the aliphatic hydrocarbon group may be replaced with -O- or -CO-, and -CH 2 - contained in the cyclic hydrocarbon group may be replaced with -O-, -S-, -SO 2 - or -CO-. ) The resist composition according to [Invention 1] or [Invention 2].

[0022] [Invention 4] X 0 is a single bond, an aliphatic hydrocarbon group having 1 to 18 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, a group formed by combining an alicyclic hydrocarbon group having 3 to 36 carbon atoms and an aliphatic hydrocarbon group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 36 carbon atoms, or a group formed by combining an aromatic hydrocarbon group having 6 to 36 carbon atoms and an aliphatic hydrocarbon group having 1 to 18 carbon atoms, -CH 2 - contained in the aliphatic hydrocarbon group and the alicyclic hydrocarbon group may be replaced with -O-, -S-, -CO- or -SO 2 -, the alicyclic hydrocarbon group, the aromatic hydrocarbon group and the aliphatic hydrocarbon group may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group. The resist composition according to any one of [Invention 1] to [Invention 3].

[0023] [Invention 5] The resist composition according to any one of [Invention 1] to [Invention 4], wherein the structural unit having the group represented by the formula (II-x) is the structural unit represented by the formula (IIA).

[0024] [Chemical formula]

[0025] [In the formula (IIA), R x represents an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, a hydrogen atom or a halogen atom. A X represents a single bond, -A X1 -*, or -CO-O-A X1 -* (* represents the bonding site with the carbonyl group).

[0026] A X1 represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH 2 - in the saturated hydrocarbon group may be replaced by -O-, -CO-, or -N(R d )-. Ring W 1 represents a heterocyclic ring having 2 to 36 carbon atoms, and a hydrogen atom in the heterocyclic ring may be substituted by a halogen atom or a hydrocarbon group having 1 to 24 carbon atoms, and -CH 2 - in the heterocyclic ring and the hydrocarbon group may be replaced by -O-, -S-, -CO-, or -NR c - group.

[0027] R c and R d each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. [Invention 6] The resin further includes a structural unit having an acid-labile group, and the resist composition according to any one of [Invention 1] to [Invention 5], wherein the structural unit having an acid-labile group includes 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).

[0028] [Chemical formula]

[0029] [In formulas (a1-0), (a1-1), and (a1-2), L a01 , L a1 and L a2Each independently represents -O- or *-O-(CH 2 ) k1 -CO-O-, k1 represents an integer from 1 to 7, and * represents the bonding site with -CO-.

[0030] R a01 、R a4 and R a5 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a02 、R a03 and R a04 each independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these, and the alkyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may have a halogen atom.

[0031] 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 combining these, and the alkyl group, the alkenyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may have a halogen atom.

[0032] m1 represents an integer from 0 to 14. n1 represents an integer from 0 to 10. n1′ represents an integer from 0 to 3.]

[0033]

Chemical formula

[0034] [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.

[0035] Ra17 represents a halogen atom, a hydroxy group, a carboxy group, an optionally halogenated 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.

[0036] A a11 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and -CH 2 - contained in the alkanediyl group may be replaced by -O-, -CO- or -NR a18 -.

[0037] 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 represent 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 -CH 2 - contained in the hydrocarbon group and the divalent hydrocarbon group may be replaced by -O- or -S-.

[0038] na1 represents any integer from 1 to 5, and when na1 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. na11 represents any integer from 0 to 4, and when na11 is 2 or more, the plurality of R a17 may be the same as or different from each other.

[0039] mc represents any integer from 0 to 2.

[0040]

Chemical formula

[0041] 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.

[0042] Z a1 represents a single bond or *-(CH 2 ) h3 -CO-L 54 -, h3 represents an integer of any one of 1 to 4, and * represents the bonding site with L 51 . L 51 , L 52 , L 53 and L 54 each independently represents -O- or -S-.

[0043] s1 represents an integer of any one of 1 to 3. s1′ represents an integer of any one of 0 to 3.]

[0044]

Chemical formula

[0045] 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.

[0046] 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 atom to which they are bonded.

[0047] X a61represents a single bond, -CO-O-* or -CO-NR a65 -, where * represents the bonding site with Ar, and R a65 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a62 represents a single bond, *-O-L a61 - or *-CO-O-L a62 -, where * represents the bonding site with -Ar, and L a61 and L a62 each independently represents an alkanediyl group having 1 to 4 carbon atoms.

[0048] Ar represents an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent. [Invention 7] The resist composition according to any one of [Invention 1] to [Invention 6], wherein the resin further contains a structural unit represented by the formula (a2-A).

[0049] [Chemical formula]

[0050] [In the 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.

[0051] 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.

[0052] A a21 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and -CH 2 - contained in the alkanediyl group may be replaced by -O-, -CO- or -NR a28 -.

[0053] 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 any integer from 1 to 5. When nA2 is 2 or more, the groups within the plurality of parentheses may be the same as or different from each other.

[0054] na21 represents any integer from 0 to 4. When na21 is 2 or more, the plurality of Rs a27 may be the same as or different from each other. mc represents any integer from 0 to 2. [Invention 8] further containing an acid generator, the resist composition according to any one of [Invention 1] to [Invention 7], wherein the acid generator contains a salt represented by formula (B1).

[0055]

Chemical formula

[0056] [In formula (B1), L b1 represents a single bond or an optionally substituted (nb1 + 1)-valent hydrocarbon group, and -CH 2 - in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -.

[0057] L b2 represents a single bond or an optionally substituted divalent hydrocarbon group having 1 to 24 carbon atoms, and -CH 2 - in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -.

[0058] Y b1represents 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 - may be replaced by -O-, -S-, -SO 2 - or -CO-.

[0059] nb1 represents any integer from 1 to 6. When nb1 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. Z + represents an organic cation.] [Invention 9] (1) A step of applying the resist composition according to any one of [Invention 1] to [Invention 8] on a substrate, (2) A step of drying the applied resist composition to form a composition layer, (3) A step of exposing the composition layer, (4) A step of heating the exposed composition layer, and (5) A step of developing the heated composition layer, A method for producing a resist pattern including

Advantages of the Invention

[0060] According to the present invention, a resist pattern having good pattern collapse resistance (PCM) can be produced.

Modes for Carrying Out the Invention

[0061] In this specification, the “(meth)acrylic monomer” means “at least one of an acrylic monomer and a methacrylic monomer”. Descriptions such as “(meth)acrylate” and “(meth)acrylic acid” also have the same meaning. Among the groups described in this specification, those which can take both a linear structure and a branched structure may be either of them. -CH 2 - is -O-, -S-, -CO- or -SO 2When it is replaced with -, the same examples shall be applied to each group, and the number of carbon atoms before replacement shall be taken as the number of carbon atoms of the hydrocarbon group or the like. The "combined group" means a group formed by combining two or more of the exemplified groups with appropriate changes in their valences, bonding forms, etc. "Derived from" or "derived" means that the polymerizable C=C bond contained in the molecule becomes a single bond (-C-C-) by polymerization. When stereoisomers exist, all stereoisomers are included. The "acid-labile group" means a group having a leaving group, and when contacted with an acid (e.g., trifluoromethanesulfonic acid, etc.), the leaving group is eliminated to form a hydrophilic group (e.g., hydroxy group or carboxy group, etc.). The "base-labile group" means a group having a leaving group, and when contacted with a base (e.g., trimethylamine, etc.), the leaving group is eliminated to form a hydrophilic group (e.g., hydroxy group or carboxy group, etc.). Each group may have any position and number of hydrogen atoms contained in the group replaced at the bonding site depending on the number of substituents, etc. The number of carbon atoms in the substituent is not included in the number of carbon atoms of the group being substituted.

[0062] In this specification, the "solid content of the resist composition" means the total of the components excluding the solvent (E) described later from the total amount of the resist composition. 〈Resist Composition〉 The resist composition of the present invention contains a resin (hereinafter sometimes referred to as "resin (A)") including a structural unit represented by formula (I) (hereinafter sometimes referred to as "structural unit (I)") and a structural unit having a group represented by formula (II-x) (hereinafter sometimes referred to as "structural unit (II)").

[0063] The resist composition of the present invention preferably further contains a resin other than resin (A) (hereinafter sometimes referred to as "resin (X)"), an acid generator (hereinafter sometimes referred to as "acid generator (B)"), a quencher (hereinafter sometimes referred to as "quencher (C)") and / or a solvent (hereinafter sometimes referred to as "solvent (E)").

[0064] 〈Resin (A)〉 Resin (A) is a resin containing structural unit (I) and structural unit (II). Resin (A) may contain structural units known in the art other than structural unit (I) and structural unit (II).

[0065] (Structural unit (I)) Structural unit (I) is a structural unit represented by the following formula (I), and for example, it is derived from an ammonium carboxylate salt represented by the following formula (I-s) (hereinafter sometimes referred to as salt (I-s)) that can function as an acid generator, and the CH 2 =C-R 10 is in a state where the double bond has cleaved.

[0066] Among salts (I-s), the side with a negative charge may be referred to as "anion (I-a)", and the side with a positive charge may be referred to as "cation (I-c)".

[0067] [Chemical formula]

[0068] [In formula (I) and formula (I-s), all symbols have the same meanings as described above.] X 0 Examples of the hydrocarbon group represented by include aliphatic hydrocarbon groups (chain hydrocarbon groups such as alkanediyl groups, alkenediyl groups, and alkynediyl groups, and alicyclic hydrocarbon groups), aromatic hydrocarbon groups, and groups combining these. The -CH 2 - contained in the hydrocarbon group may be replaced by -O-, -S-, -CO-, or -SO 2 -. In the hydrocarbon group, the atom adjacent to CO 2 - is preferably a carbon atom, and in the aliphatic hydrocarbon group, the atom adjacent to CO 2 - is more preferably a carbon atom.

[0069] Examples of the alkanediyl group include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group; and branched alkanediyl groups such as ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group, propane-2,2-diyl group, pentane-2,4-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group. The terminal of the branched alkanediyl group may be a methyl group.

[0070] Examples of the alkenediyl group include ethenediyl group, propenediyl group, isopropenediyl group, butenediyl group, isobutenediyl group, tert-butenediyl group, pentenediyl group, hexenediyl group, heptenediyl group, octenediyl group, isooctenediyl group, nonenediyl group.

[0071] Examples of the alkynediyl group include ethynediyl group, propynediyl group, isopropynediyl group, butynediyl group, isobutynediyl group, tert-butynediyl group, pentynediyl group, hexynediyl group, octynediyl group, nonynediyl group and the like.

[0072] The number of carbon atoms of the chain hydrocarbon group is preferably from 1 to 48, more preferably from 1 to 18, still more preferably from 1 to 12, further preferably from 1 to 9, even more preferably from 1 to 6, still even more preferably from 1 to 4, and still further preferably from 1 to 3.

[0073] For the group in which -CH 2 - in the hydrocarbon group is replaced by -O-, -S-, -CO- or -SO 2 -, examples of the group include a hydroxy group (-CH contained in a methyl group 2- is a group replaced by -O-), a carboxy group (-CH contained in the ethyl group) 2 -CH 2 - is a group replaced by -O-CO-), a thiol group (-CH contained in the methyl group) 2 - is a group replaced by -S-), a carbonyl group (-CH contained in the methylene group) 2 - is a group replaced by -CO-), a sulfonyl group (-CH contained in the methylene group) 2 - is 2 - replaced by -SO-), an oxy group (-CH contained in the methylene group) 2 - is a group replaced by -O-), an alkoxy group (-CH at any position contained in the alkyl group) 2 - is a group replaced by -O-), an alkoxycarbonyl group (-CH at any position contained in the alkyl group) 2 -CH 2 - is a group replaced by -O-CO-), an alkylcarbonyl group (-CH at any position contained in the alkyl group) 2 - is a group replaced by -CO-), an alkylsulfonyl group (-CH at any position contained in the alkyl group) 2 - is 2 - replaced by -SO-), an alkylcarbonyloxy group (-CH at any position contained in the alkyl group) 2 -CH 2 - is a group replaced by -CO-O-), an alkylthio group (-CH at any position contained in the alkyl group) 2 - is a group replaced by -S-), an alkanedioxy group (-CH at any position contained in the alkanediyl group) 2 - is a group replaced by -O-), an alkanedioxycarbonyl group (-CH at any position contained in the alkanediyl group) 2 -CH 2 - is a group replaced by -O-CO-), an alkanediylcarbonyl group (-CH at any position contained in the alkanediyl group) 2 - is a group replaced by -CO-), an alkanediylcarbonyloxy group (-CH at any position contained in the alkanediyl group) 2 -CH 2- is a group replaced by -CO-O-, an alkanediylsulfonyl group (any -CH at any position contained in the alkanediyl group) 2 - is 2 - a group replaced by -SO 2 - a group replaced by -S-, a group formed by combining two or more of these groups, etc.

[0074] Examples of the alkoxy group include alkoxy groups having 1 to 71 carbon atoms, such as methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, undecyloxy group and the like. The number of carbon atoms of the alkoxy group is preferably 1 to 47, may be 1 to 35, preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0075] Examples of the alkylthio group include alkylthio groups having 1 to 27 carbon atoms, such as methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group, hexylthio group, octylthio group, 2-ethylhexylthio group, nonylthio group, decylthio group, undecylthio group and the like. The number of carbon atoms of the alkylthio group is preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0076] Examples of the alkoxycarbonyl group include alkoxycarbonyl groups having 2 to 71 carbon atoms, such as methoxycarbonyl group, ethoxycarbonyl group, butoxycarbonyl group and the like. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 72 carbon atoms, such as acetyl group, propionyl group and butyryl group. Examples of the alkylcarbonyloxy group include alkylcarbonyloxy groups having 2 to 71 carbon atoms, such as acetyloxy group, propionyloxy group, butyryloxy group and the like. The number of carbon atoms of the alkoxycarbonyl group may be 2 to 47, may be 2 to 35, preferably 2 to 11, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms of the alkylcarbonyl group may be 2 to 48, may be 2 to 36, preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms of the alkylcarbonyloxy group may be 2 to 47, may be 2 to 35, preferably 2 to 11, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3.

[0077] Examples of the alkylsulfonyl group include alkylsulfonyl groups having 1 to 71 carbon atoms, such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, octylsulfonyl group, 2-ethylhexylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, undecylsulfonyl group and the like. The number of carbon atoms of the alkylsulfonyl group may be 1 to 47, may be 1 to 35, preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0078] Examples of the alkanediyl-oxy group include alkanediyl-oxy groups having 1 to 71 carbon atoms, such as a methylene-oxy group, an ethylene-oxy group, a propane-diyl-oxy group, a butane-diyl-oxy group, and a pentane-diyl-oxy group. The number of carbon atoms of the alkanediyl-oxy group is preferably 1 to 47, more preferably 1 to 35, still more preferably 1 to 11, even more preferably 1 to 6, still even more preferably 1 to 4, and most preferably 1 to 3.

[0079] Examples of the alkanediyl-oxycarbonyl group include alkanediyl-oxycarbonyl groups having 2 to 71 carbon atoms, such as a methylene-oxycarbonyl group, an ethylene-oxycarbonyl group, a propane-diyl-oxycarbonyl group, and a butane-diyl-oxycarbonyl group. Examples of the alkanediyl-carbonyl group include alkanediyl-carbonyl groups having 2 to 72 carbon atoms, such as a methylene-carbonyl group, an ethylene-carbonyl group, a propane-diyl-carbonyl group, a butane-diyl-carbonyl group, and a pentane-diyl-carbonyl group. Examples of the alkanediyl-carbonyloxy group include alkanediyl-carbonyloxy groups having 2 to 71 carbon atoms, such as a methylene-carbonyloxy group, an ethylene-carbonyloxy group, a propane-diyl-carbonyloxy group, and a butane-diyl-carbonyloxy group. The number of carbon atoms of the alkanediyl-oxycarbonyl group is preferably 2 to 47, more preferably 2 to 35, still more preferably 2 to 11, even more preferably 2 to 6, still even more preferably 2 to 4, and most preferably 2 or 3. The number of carbon atoms of the alkanediyl-carbonyl group is preferably 2 to 48, more preferably 2 to 36, still more preferably 2 to 12, even more preferably 2 to 6, still even more preferably 2 to 4, and most preferably 2 or 3. The number of carbon atoms of the alkanediyl-carbonyloxy group is preferably 2 to 47, more preferably 2 to 35, still more preferably 2 to 11, even more preferably 2 to 6, still even more preferably 2 to 4, and most preferably 2 or 3.

[0080] Examples of the alkanediylsulfonyl group include alkanediylsulfonyl groups having 1 to 71 carbon atoms, such as a methylenesulfonyl group, an ethylenesulfonyl group, and a propylenesulfonyl group. The number of carbon atoms of the alkanediylsulfonyl group may be 1 to 47, may be 1 to 35, preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0081] Examples of the alkanediylthio group include alkanediylthio groups having 1 to 71 carbon atoms, such as a methylenethio group, an ethylenethio group, and a propylenethio group. The number of carbon atoms of the alkanediylthio group may be 1 to 47, may be 1 to 35, preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0082] In the alkenediyl group and the alkynediyl group, the substitution may be any one that contains a carbon-carbon double bond or a carbon-carbon triple bond at an arbitrary position in the examples of the substitution in the above-described alkanediyl group.

[0083] The alicyclic hydrocarbon group may be monocyclic, polycyclic, or spirocyclic, and may be saturated or unsaturated. Examples of the alicyclic hydrocarbon group include the groups represented below. The bonding site can be at any position.

[0084]

Chemical formula

[0085] Specifically, examples of the monocyclic divalent alicyclic hydrocarbon group include monocyclic cycloalkanediyl groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclohexene-3,6-diyl group, cyclooctane-1,5-diyl group, etc. Examples of the polycyclic divalent alicyclic hydrocarbon group include polycyclic cycloalkanediyl groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, 5-norbornene-2,3-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, etc.

[0086] The number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 48, more preferably 3 to 36, still more preferably 3 to 24, yet more preferably 3 to 18, even more preferably 3 to 16, and still even more preferably 3 to 12.

[0087] -CH 2 - in the alicyclic hydrocarbon group replaced by -O-, -S-, -CO- or -SO 2 - may form an ether ring, a ketone ring, a lactone ring, a sultone ring or an acetal ring. Specifically, examples include the following groups. The bonding site can be at any position.

[0088]

Chemical formula

[0089] As the alicyclic hydrocarbon group, a group represented by any of formula (y1) to formula (y11), formula (y44) to formula (y48), and formula (y59) to formula (y61) is preferable, and a group represented by any of formula (y3), formula (y4), formula (y9), and formula (y11) is more preferable.

[0090] -CH 2 - in the alicyclic hydrocarbon group replaced by -O-, -S-, -CO- or -SO 2As the group replaced by -, a group represented by any of formula (y12) to formula (y20), formula (y26), formula (y27), formula (y30), formula (y31), formula (y39) to formula (y43), and formula (y49) to formula (y71) is preferable, and a group represented by any of formula (y14), formula (y15), formula (y16), formula (y20), formula (y26), formula (y27), formula (y30), formula (y31), formula (y39), formula (y40), formula (y42), formula (y43), formula (y49) to formula (y58), and formula (y62) to formula (y71) is more preferable.

[0091] Examples of the aromatic hydrocarbon group include a phenylene group, a naphthylene group, an anthrylene group, a biphenylene group, a phenanthrylene group, etc. The number of carbon atoms of the aromatic hydrocarbon group is 6 to 48, preferably 6 to 36, more preferably 6 to 24, still more preferably 6 to 18, even more preferably 6 to 14, and even more preferably 6 to 10.

[0092] Examples of the hydrocarbon group combined with two or more types include a group combining an alkanediyl group with an alicyclic hydrocarbon group and / or an aromatic hydrocarbon group, etc., such as -alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-alicyclic hydrocarbon group-, -alkanediyl group-alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-aromatic hydrocarbon group-, -aromatic hydrocarbon group-alkanediyl group-, etc. Further, in the case of a group combining an alicyclic hydrocarbon group or an aromatic hydrocarbon group with an alkanediyl group, the terminal of the alkanediyl group may be an alkyl group such as a methyl group.

[0093] X 0 In the hydrocarbon group represented by, when -CH 2 - is replaced by -O-, -S-, -CO- or -SO 2 -, the total number of carbon atoms of the hydrocarbon group before replacement is taken as the total number of carbon atoms of the hydrocarbon group. Further, when a substituent is bonded to the hydrocarbon group represented by X 0 the total number of carbon atoms before substitution is taken as the total number of carbon atoms of the hydrocarbon group.

[0094] -CH contained in a group combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group 2 - is replaced by -O-, -S-, -CO- or -SO 2 - Examples of the group thus replaced include the following groups and the like. The bonding site can be at any position.

[0095]

Chemical formula

[0096] X 0 The hydrocarbon group represented by may have one or more substituents. Examples of the substituent include a hydroxy group, a halogen atom, a cyano group, a nitro group and the like. X 0 When contains a group combining an alicyclic hydrocarbon group or an aromatic hydrocarbon group and a chain hydrocarbon group, the chain hydrocarbon group bonded to the alicyclic hydrocarbon group or the aromatic hydrocarbon group contained in X 0 can be substantially regarded as a substituent of X 0 Also, when -CH 0 - contained in the hydrocarbon group of X 2 - is replaced by -O-, -S-, -SO 2 - or -CO-, X 0 can substantially have substituents such as a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkylthio group, an alkylsulfonyl group and the like.

[0097] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom and the like. X 0 The hydrocarbon group represented by is preferably an aliphatic hydrocarbon group having 1 to 72 carbon atoms which may have substituents (wherein -CH 2 - contained in the aliphatic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -), or an aromatic hydrocarbon group having 6 to 36 carbon atoms which may have substituents, More preferably, it is an optionally substituted chain hydrocarbon group having 1 to 18 carbon atoms (wherein -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-).), an optionally substituted alicyclic hydrocarbon group having 3 to 36 carbon atoms (wherein -CH 2 - in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -).), a group combining an optionally substituted alicyclic hydrocarbon group having 3 to 36 carbon atoms and an optionally substituted chain hydrocarbon group having 1 to 18 carbon atoms (wherein -CH 2 - in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -, and -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-).), an optionally substituted aromatic hydrocarbon group having 6 to 36 carbon atoms or a group combining an optionally substituted aromatic hydrocarbon group having 6 to 36 carbon atoms and an optionally substituted chain hydrocarbon group having 1 to 18 carbon atoms (wherein -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-).), and More preferably, *-chain hydrocarbon group-, *-alicyclic hydrocarbon group-, *-group combining an alicyclic hydrocarbon group and a chain hydrocarbon group-, *-alicyclic hydrocarbon group-chain hydrocarbon group-, *-chain hydrocarbon group-alicyclic hydrocarbon group-, *-group combining an alicyclic hydrocarbon group and a chain hydrocarbon group-chain hydrocarbon group-, *-chain hydrocarbon group-alicyclic hydrocarbon group and a group combining a chain hydrocarbon group-, *-aromatic hydrocarbon group-, *-chain hydrocarbon group-aromatic hydrocarbon group-, *-aromatic hydrocarbon group-chain hydrocarbon group-, *-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-, *-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-, *-group combining an alicyclic hydrocarbon group and a chain hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-, *-chain hydrocarbon group-alicyclic hydrocarbon group and a group combining a chain hydrocarbon group-chain hydrocarbon group-, *-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-, or *-chain hydrocarbon group-alicyclic hydrocarbon group and a group combining a chain hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-(the -CH contained in the alicyclic hydrocarbon group 2 - may be replaced by -O-, -S-, -CO- or -SO 2 -, and the -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO-, and the alicyclic hydrocarbon group, the aromatic hydrocarbon group and the chain hydrocarbon group may have a substituent. * is -COO - represents the bonding site to the carbon atom of.). And Even more preferably, *-alicyclic hydrocarbon group-, *-alicyclic hydrocarbon group-chain hydrocarbon group-, *-chain hydrocarbon group-alicyclic hydrocarbon group-, *-aromatic hydrocarbon group- or *-chain hydrocarbon group-aromatic hydrocarbon group-(the -CH contained in the alicyclic hydrocarbon group 2 - may be replaced by -O-, -S-, -CO- or -SO 2 -, and the -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO-, and the alicyclic hydrocarbon group, the chain hydrocarbon group and the aromatic hydrocarbon group may have a halogen atom, a C1-C4 perfluoroalkyl group or a hydroxy group. * is -COO- represents the bonding site with the carbon atom. Even more preferably, *-monocyclic alicyclic hydrocarbon group-, *-polycyclic alicyclic hydrocarbon group-, *-polycyclic alicyclic hydrocarbon group-chain hydrocarbon group-, *-chain hydrocarbon group-polycyclic alicyclic hydrocarbon group-, *-aromatic hydrocarbon group- or *-chain hydrocarbon group-aromatic hydrocarbon group- (the -CH 2 - in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 - and the -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-. The alicyclic hydrocarbon group and the chain hydrocarbon group may have a fluorine atom or a hydroxy group, and the aromatic hydrocarbon group may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group. * is -COO - represents the bonding site with the carbon atom.

[0098] In the above groups, the number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 36, more preferably 3 to 24, still more preferably 3 to 18, even more preferably 3 to 16, and even more preferably 3 to 12. The number of carbon atoms of the chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 12, still more preferably 1 to 9, even more preferably 1 to 6, and even more preferably 1 to 4. The number of carbon atoms of 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 even more preferably 6 to 10.

[0099] In the above groups, the alicyclic hydrocarbon group or the aromatic hydrocarbon group is an alicyclic hydrocarbon group having 3 to 18 carbon atoms or an aromatic hydrocarbon group having 6 to 18 carbon atoms (the -CH 2 - in the group may be replaced by -O-, -S-, -CO- or -SO 2- may be replaced therewith. It is preferably such that, more preferably it is a group represented by any one of formula (w1-1) to formula (w1-28), still more preferably it is a group represented by any one of formula (w1-1) to formula (w1-6) and formula (w1-12) to formula (w1-26), and still even more preferably it is a group represented by any one of formula (w1-1) to formula (w1-3), formula (w1-6), formula (w1-15) to formula (w1-17), formula (w1-22) and formula (w1-25).

[0100] [Chemical formula]

[0101] [In formula (w1-1) to formula (w1-28), -CH 2 - contained in the group may be replaced with -O-, -S-, -CO- or -SO 2 -. The bonding site may be at any position.] More specifically, the above monocyclic alicyclic hydrocarbon group is preferably a cycloalkanediyl group having 5 or 6 carbon atoms (wherein -CH 2 - contained in the cycloalkanediyl group may be replaced with -O- or -CO-), the above polycyclic alicyclic hydrocarbon group is preferably an adamantanediyl group, a norbornanediyl group, an adamantanlactonediyl group, a norbornanlactonediyl group, a polycyclic alicyclic hydrocarbon group in which a cycloalkanediyl group having 5 or 6 carbon atoms and a cycloalkanediyl group having 5 to 8 carbon atoms are spiro-bonded, a polycyclic alicyclic hydrocarbon group in which a norbornanediyl group and a cycloalkanediyl group having 5 to 8 carbon atoms are spiro-bonded, or a polycyclic alicyclic hydrocarbon group in which an adamantanediyl group and a cycloalkanediyl group having 5 to 8 carbon atoms are spiro-bonded, and the above aromatic hydrocarbon group is preferably a phenylene group. Here, -CH 2 -CH 2 - contained in the adamantanediyl group and the norbornanediyl group may be replaced with -O-CO-, and the cycloalkanediyl group may be an acetal ring.

[0102] Based on the above, the chain hydrocarbon group is preferably a chain hydrocarbon group having 1 to 12 carbon atoms (the -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-).), more preferably a chain hydrocarbon group having 1 to 8 carbon atoms (the -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-).), still more preferably an alkanediyl group having 1 to 6 carbon atoms (the -CH 2 - in the alkanediyl group may be replaced by -O- or -CO-).). It is also preferable to have a fluorine atom.

[0103] In the above chain hydrocarbon group and alicyclic hydrocarbon group, the substituent is preferably a halogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 3 to 10 carbon atoms or a group combining these, more preferably a fluorine atom, a hydroxy group or a perfluoroalkyl group having 1 to 4 carbon atoms.

[0104] In the above aromatic hydrocarbon group, the substituent is preferably a halogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 3 to 10 carbon atoms or a group combining these, more preferably a fluorine atom, an iodine atom, a hydroxy group or a perfluoroalkyl group having 1 to 4 carbon atoms.

[0105] More specifically, X 0 is preferably a single bond or an aliphatic hydrocarbon group having 1 to 72 carbon atoms which may have a substituent (the -CH 2 - in the aliphatic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -), or a hydrocarbon group having 6 to 72 carbon atoms containing an aromatic hydrocarbon group having 6 to 36 carbon atoms (the -CH 2 - in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -), and the aromatic hydrocarbon group and the hydrocarbon group may have a substituent.). More preferably, it is a single bond, or a chain hydrocarbon group having 1 to 18 carbon atoms which may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group (the -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-), a halogen atom, an alicyclic hydrocarbon group having 3 to 36 carbon atoms which may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group (the -CH 2 - in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -), a group combining an alicyclic hydrocarbon group having 3 to 36 carbon atoms and a chain hydrocarbon group having 1 to 18 carbon atoms (the -CH 2 - in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -), the -CH 2 - 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 halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group), a halogen atom, an aromatic hydrocarbon group having 6 to 36 carbon atoms which may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group, or a group combining an aromatic hydrocarbon group having 6 to 36 carbon atoms and a chain hydrocarbon group having 1 to 18 carbon atoms (the -CH 2 - 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).), and Even more preferably, it is a single bond, or a chain hydrocarbon group having 1 to 12 carbon atoms which may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group (the -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-), a halogen atom, an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group (the -CH 2 - in the alicyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2- may be replaced by). A group combining an alicyclic hydrocarbon group having 3 to 18 carbon atoms and a chain hydrocarbon group having 1 to 8 carbon atoms (the -CH contained in the alicyclic hydrocarbon group 2 - is -O-, -S-, -CO- or -SO 2 - may be replaced by, and the -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO-, and the alicyclic 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 halogen atom, an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group, or a group combining an aromatic hydrocarbon group having 6 to 18 carbon atoms and a chain hydrocarbon group having 1 to 8 carbon atoms (the -CH contained in the chain hydrocarbon group 2 - 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.). It contains More preferably, it is a single bond, an alkanediyl group having 1 to 6 carbon atoms, a cycloalkanediyl group having 5 or 6 carbon atoms, an adamantanediyl group, a norbornanediyl group, an adamantanlactonediyl group, a norbornanlactonediyl group, a phenylene group, a group combining an alkanediyl group having 1 to 6 carbon atoms and a cycloalkanediyl group having 5 to 6 carbon atoms, an adamantanediyl group, a norbornanediyl group or a phenylene group, a polycyclic alicyclic hydrocarbon group in which a cycloalkanediyl group having 5 to 6 carbon atoms and a cycloalkanediyl group having 5 to 8 carbon atoms are spiro-bonded, a polycyclic alicyclic hydrocarbon group in which a norbornanediyl group and a cycloalkanediyl group having 5 to 8 carbon atoms are spiro-bonded, or a polycyclic alicyclic hydrocarbon group in which an adamantanediyl group and a cycloalkanediyl group having 5 to 8 carbon atoms are spiro-bonded (the -CH contained in the alkanediyl group, the cycloalkanediyl group, the adamantanediyl group and the norbornanediyl group 2- may be replaced by -O- or -CO-. The alkandiyl group, the cycloalkanediyl group, the adamantanediyl group, the norbornanediyl group, the adamantanlactonediyl group and the norbornanlactonediyl group may have a fluorine atom, a C1-C4 perfluoroalkyl group or a hydroxy group, and the phenylene group may have a halogen atom, a C1-C4 perfluoroalkyl group or a hydroxy group.), and Even more preferably, a cyclohexanediyl group, an adamantanediyl group, a hydroxyadamantanediyl group, a norbornanlactonediyl group, a group combining an alkandiyl group having 1 to 6 carbon atoms and an adamantanediyl group (the -CH 2 - may be replaced by -O- or -CO-.), a phenylene group, or a hydroxyphenylene group.

[0106] Also, X 0 contains an alicyclic hydrocarbon group, and the alicyclic hydrocarbon group is a C5-C6 cycloalkanediyl group, an adamantanediyl group, a norbornanediyl group, an adamantanlactonediyl group, a norbornanlactonediyl group, a polycyclic alicyclic hydrocarbon group in which a C5-C6 cycloalkanediyl group and a C5-C8 cycloalkanediyl group are spiro-bonded, a polycyclic alicyclic hydrocarbon group in which a norbornanediyl group and a C5-C8 cycloalkanediyl group are spiro-bonded or a polycyclic alicyclic hydrocarbon group in which an adamantanediyl group and a C5-C8 cycloalkanediyl group are spiro-bonded (the adamantanediyl group, the norbornanediyl group and the cycloalkanediyl group may have a fluorine atom, a C1-C4 perfluoroalkyl group or a hydroxy group, and the -CH 2 - may be replaced by -O- or -CO-). Here, the -CH 2 -CH 2- may be replaced by -O-CO-, and the cycloalkanediyl group may be an acetal ring.

[0107] R 10 Examples of the halogen atom of R include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. R 10 Examples of the alkyl group of R include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexyl group, etc.

[0108] R 10 Examples of the alkyl group having 1 to 6 carbon atoms with a halogen atom of R include an alkyl fluoride group having 1 to 6 carbon atoms, an alkyl chloride group having 1 to 6 carbon atoms, an alkyl bromide group having 1 to 6 carbon atoms, an alkyl iodide group having 1 to 6 carbon atoms, etc. Specifically, 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 perfluoro sec-butyl group, a perfluoro tert-butyl group, a perfluoropentyl group, a perfluorohexyl group, a perchloromethyl group, a perbromomethyl group, and a periodomethyl group, etc.

[0109] The carbon number of the alkyl group, alkyl fluoride group, alkyl chloride group, alkyl bromide group, and alkyl iodide group is preferably 1 to 4, more preferably 1 to 3, and even more preferably 1 or 2.

[0110] R 10 R is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, even more preferably a hydrogen atom or a methyl group, and even more preferably a methyl group.

[0111] R 9 Examples of the alkyl group of R include the same groups as R within the range of 1 to 6 carbon atoms. 10 X 10 ​When it is a group represented by *-Ax-Ph-Ay-*, it is preferably a linking group represented by the following formula (X10).

[0112] [Chemical formula]

[0113] [In formula (X10), Ax represents the bonding species that binds to the carbon atom to which R 10 is attached, and represents one or more bonding species selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, an amide bond, and a carbonate ester bond.

[0114] Ay represents the bonding species that binds to L 10 or COO - and represents one or more bonding species selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, an amide bond, and a carbonate ester bond.

[0115] Rx represents a halogen atom, a hydroxy group, a fluorinated alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. mx represents any integer from 0 to 4, and when mx is an integer of 2 or more, the plurality of Rx may be the same as or different from each other.] When either Ax or Ay is a single bond, the other is preferably one or more selected from the group consisting of an ether bond, a thioether bond, an ester bond, an amide bond, and a carbonate ester bond.

[0116] When either Ax or Ay is an amide bond, it is preferably a bond represented by -CO-NR 9 -. Rx is preferably a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, or an ethyl group.

[0117] mx is preferably 0, 1, or 2. The bonding position of Ay in the phenylene group is preferably the meta-position or the para-position with respect to the bonding position of Ax, and more preferably the para-position.

[0118] X 10 Examples of [X 10 -1] to [X 10 -10] include groups represented by any of the following formulas. * represents the bonding site with the carbon atom to which -R 10 is bonded. ** represents the bonding site with L 10 or COO - is bonded.

[0119]

Chemical formula

[0120] [In formulas [X 10 -1] to [X 10 -10], *, ** are bonding sites, and * represents the bonding site with the carbon atom to which R 10 is bonded. Rx represents a halogen atom, a hydroxy group, a fluorinated alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.

[0121] mx represents any integer from 0 to 4. X 20 represents -O- or -NR 9 -. R 9 represents the same meaning as in formula (I).] Specific examples of the groups represented by formulas [X 10 -1] to [X 10 -10] include the following groups.

[0122]

Chemical formula

[0123] Among them, X 20 is a single bond or a formula [X 10-1′) and formula (X 10 -3′) to formula (X 10 10′), and is preferably a group represented by any of them, a single bond or formula (X 10 -1′), formula (X 10 -4′), formula (X 10 -5′), formula (X 10 -6′) and formula (X 10 -10′), and is more preferably a group represented by any of them, a single bond, a group represented by formula (X 10 -1′), a group represented by formula (X 10 -5′) or a group represented by formula (X 10 -6′).

[0124] L 10 The hydrocarbon group having 1 to 36 carbon atoms for L includes aliphatic hydrocarbon groups (chain hydrocarbon groups such as alkanediyl groups, alkenediyl groups, and alkynediyl groups and alicyclic hydrocarbon groups), aromatic hydrocarbon groups, etc., and may be a hydrocarbon group obtained by combining two or more of these groups.

[0125] Examples of the alkanediyl group include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group; and branched alkanediyl groups such as ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group, propane-2,2-diyl group, pentane-2,4-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group. The terminal of the branched alkanediyl group may be a methyl group. Examples of the alkenediyl group include ethenediyl group, propenediyl group, isopropenediyl group, butenediyl group, isobutenediyl group, tert-butenediyl group, pentenediyl group, hexenediyl group, heptenediyl group, octenediyl group, isooctenediyl group, nonenediyl group.

[0126] Examples of the alkynediyl group include ethyndiyl group, propyndiyl group, isopropyndiyl group, butyndiyl group, isobutyndiyl group, tert-butyndiyl group, pentyndiyl group, hexyndiyl group, octyndiyl group, nonyndiyl group and the like.

[0127] The number of carbon atoms of the chain hydrocarbon group is preferably 1 to 12, more preferably 1 to 9, still more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3.

[0128] The divalent alicyclic hydrocarbon group may be monocyclic, polycyclic or spirocyclic. Examples of the divalent alicyclic hydrocarbon group include the groups represented below. The bonding site can be at any position.

[0129]

Chemical formula

[0130] Specifically, examples of the monocyclic divalent alicyclic hydrocarbon group include monocyclic cycloalkanediyl groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclohexene-3,6-diyl group, cyclooctane-1,5-diyl group, etc. Examples of the polycyclic divalent alicyclic hydrocarbon group include polycyclic cycloalkanediyl groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, 5-norbornene-2,3-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, etc.

[0131] The number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 18, more preferably 3 to 16, and still more preferably 3 to 12. Examples of the divalent aromatic hydrocarbon group include phenylene group, naphthylene group, anthrylene group, biphenylene group, phenanthrylene group, etc. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 14, and still more preferably 6 to 10.

[0132] Examples of the hydrocarbon group combined with two or more types include a group combining an alkanediyl group with an alicyclic hydrocarbon group and / or an aromatic hydrocarbon group, etc., such as -alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-alicyclic hydrocarbon group-, -alkanediyl group-alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-aromatic hydrocarbon group-, -aromatic hydrocarbon group-alkanediyl group-, etc. Also, in the case of a group combining an alicyclic hydrocarbon group or an aromatic hydrocarbon group with an alkanediyl group, the terminal of the alkanediyl group may be an alkyl group such as a methyl group.

[0133] L 10 The -CH 2 - contained in the hydrocarbon group having 1 to 36 carbon atoms of 2 L may be replaced by -O-, -S-, -CO- or -SO L 10When the hydrocarbon group having 1 to 36 carbon atoms has a substituent or -CH contained in the hydrocarbon group 2 - is replaced by -O-, -S-, -CO- or -SO 2 -, the number of carbon atoms before replacement is taken as the number of carbon atoms of the hydrocarbon group.

[0134] -CH contained in the hydrocarbon group 2 - is replaced by -O-, -S-, -SO 2 - or -CO-, examples of the group thus replaced include a hydroxy group, a carboxy group, a thiol group, a carbonyl group, a sulfonyl group, an oxy group, a thio group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkanedioxy group, an alkanedioxycarbonyl group, an alkanediylcarbonyl group, an alkanediylcarbonyloxy group, an alkylthio group, an alkylsulfonyl group, an alkanediylsulfonyl group, an alkanediylthio group, a cycloalkoxy group, a cycloalkylalkoxy group, an alkoxycarbonyloxy group, an aromatic hydrocarbon group-carbonyl-oxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy group, a group formed by combining two or more of these groups, etc. These replaced groups include those similar to the groups exemplified in this specification within the range where the upper limit of the number of carbon atoms permits.

[0135] L 10 Examples of the substituent that the hydrocarbon group of L may have include a halogen atom, a cyano group, a nitro group, etc. L 10 When L contains a group formed by combining an alicyclic hydrocarbon group or an aromatic hydrocarbon group and a chain hydrocarbon group such as an alkanediyl group (the ends of the alkanediyl group may be an alkyl group such as a methyl group), the chain hydrocarbon group such as the alkanediyl group bonded to the alicyclic hydrocarbon group or the aromatic hydrocarbon group can be substantially regarded as a substituent of the alicyclic hydrocarbon group or the aromatic hydrocarbon group. L 10 -CH contained in the hydrocarbon group of L 2 - is replaced by a group such as -O- or -CO-, and L 10can substantially have substituents such as hydroxy group, carboxy group, alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, alkylcarbonyloxy group, etc.

[0136] Examples of the halogen atom include fluorine atom, chlorine atom, bromine atom, iodine atom, etc. L 10 The hydrocarbon group having 1 to 36 carbon atoms of L may have one substituent or a plurality of substituents.

[0137] L 10 is a single bond, a chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent (provided that -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-), a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent (provided that -CH 2 - in the cyclic hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -), or a group formed by combining a chain hydrocarbon group having 1 to 8 carbon atoms which may have a substituent and a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent (provided that -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-, and -CH 2 - in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO 2 - or -CO-). Preferably, it is a single bond, an alkanediyl group having 1 to 6 carbon atoms (provided that -CH 2 - in the alkanediyl group may be replaced by -O- or -CO-), a cyclic hydrocarbon group having 3 to 18 carbon atoms (provided that the cyclic hydrocarbon group may have a substituent, and -CH 2 - in the cyclic hydrocarbon group may be replaced by -O-, -S-, -SO 2 - or -CO-), or a group formed by combining an alkanediyl group having 1 to 6 carbon atoms and a cyclic hydrocarbon group having 3 to 18 carbon atoms (provided that the cyclic hydrocarbon group may have a substituent, and -CH 2- may be replaced by -O- or -CO-, and -CH contained in the cyclic hydrocarbon group 2 - may be -O-, -S-, -SO 2 - or -CO-. It is more preferable that it is, a single bond, an alkanediyl group having 1 to 4 carbon atoms (provided that -CH contained in the alkanediyl group 2 - may be replaced by -O- or -CO-), an alicyclic hydrocarbon group having 3 to 18 carbon atoms (provided that -CH contained in the alicyclic hydrocarbon group 2 - may be -O-, -S-, -SO 2 - or -CO-.), an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, a group formed by combining an alkanediyl group having 1 to 4 carbon atoms and an alicyclic hydrocarbon group having 3 to 18 carbon atoms (provided that -CH contained in the alkanediyl group 2 - may be replaced by -O- or -CO-, and -CH contained in the alicyclic hydrocarbon group 2 - may be -O-, -S-, -SO 2 - or -CO-.), or a group formed by combining an alkanediyl group having 1 to 4 carbon atoms and an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent (provided that -CH contained in the alkanediyl group 2 - may be replaced by -O- or -CO-. It is even more preferable that it is, a single bond, an alkanediyl group having 1 to 4 carbon atoms (provided that -CH contained in the alkanediyl group 2 - may be replaced by -O- or -CO-), an alicyclic hydrocarbon group having 3 to 18 carbon atoms (provided that -CH contained in the alicyclic hydrocarbon group 2 - may be replaced by -O- or -CO-), a phenylene group which may have a substituent, a group formed by combining an alkanediyl group having 1 to 4 carbon atoms and an alicyclic hydrocarbon group having 3 to 18 carbon atoms (provided that -CH contained in the alkanediyl group 2 - may be replaced by -O- or -CO-, and -CH contained in the alicyclic hydrocarbon group 2- may be replaced by -O- or -CO-. ) or a group formed by combining an alkandiyl group having 1 to 4 carbon atoms and a phenylene group which may have a substituent (provided that -CH contained in the alkandiyl group 2 - may be replaced by -O- or -CO-. ) is more preferably a single bond or an alkandiyl group having 1 to 4 carbon atoms (provided that -CH contained in the alkandiyl group 2 - may be replaced by -O- or -CO-. ) is even more preferably.

[0138] Examples of the anion (I-a) include the following anions.

[0139]

Chemical formula

[0140]

Chemical formula

[0141] In the anions represented by formula (I-a-1) to formula (I-a-40), an anion in which the methyl group corresponding to R in formula (I) 10 is replaced by a hydrogen atom can also be cited as a specific example of the anion (I-a). Among them, the anions represented by formula (I-a-1) to formula (I-a-12) and formula (I-a-32) to formula (I-a-36) are preferred.

[0142] R 3 、R 4 、R 5 、R 6 and R 7 Examples of the hydrocarbon group having 1 to 20 carbon atoms of include chain hydrocarbon groups such as alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these.

[0143] The alkyl group is a linear or branched alkyl group, and examples thereof include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, octyl group, nonyl group, and decyl group.

[0144] The alkanediyl group is a linear or branched alkanediyl group, and examples thereof include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, and decane-1,10-diyl group; and branched alkanediyl groups such as ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group, propane-2,2-diyl group, pentane-2,4-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, and 2-methylbutane-1,4-diyl group.

[0145] The number of carbon atoms in the chain hydrocarbon group may be 1 to 18, preferably 1 to 12, more preferably 1 to 9, still more preferably 1 to 6, even more preferably 1 to 4, and even more preferably 1 to 3.

[0146] The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and examples of the alicyclic hydrocarbon group include groups represented below. The bonding site can be at any position.

[0147]

Chemical formula

[0148] Specifically, examples of the monocyclic alicyclic hydrocarbon group include monocyclic cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, and cyclodecyl group. Examples of the polycyclic alicyclic hydrocarbon group include polycyclic cycloalkyl groups such as decahydronaphthyl group, adamantyl group, and norbornyl group. 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.

[0149] Examples of the aromatic hydrocarbon group include phenyl group, naphthyl group, biphenyl group, anthryl group, phenanthryl group, and binaphthyl group. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 14, and even more preferably 6 to 10.

[0150] Among the chain hydrocarbon group, alicyclic hydrocarbon group, and aromatic hydrocarbon group, groups formed by combining two or more of these groups include groups combining an aromatic hydrocarbon group and a chain hydrocarbon group (for example, aromatic hydrocarbon group - alkane diyl group - *, alkyl group - aromatic hydrocarbon group - *, alkyl group - aromatic hydrocarbon group - alkane diyl group - *, -CH contained in the alkane diyl group and the alkyl group 2 - may be replaced by -O-, -CO-, -S- or -SO 2 -). Groups combining an alicyclic hydrocarbon group and a chain hydrocarbon group (for example, alicyclic hydrocarbon group - alkane diyl group - *, alkyl group - alicyclic hydrocarbon group - *, alkyl group - alicyclic hydrocarbon group - alkane diyl group - *, -CH contained in the alicyclic hydrocarbon group, the alkane diyl group and the alkyl group 2 - may be replaced by -O-, -CO-, -S- or -SO 2 -). Groups combining an aromatic hydrocarbon group and an alicyclic hydrocarbon group (for example, aromatic hydrocarbon group - alicyclic hydrocarbon group - *, alicyclic hydrocarbon group - aromatic hydrocarbon group - *, -CH contained in the alicyclic hydrocarbon group 2 - may be replaced by -O-, -CO-, -S- or -SO 2- may be substituted. * represents a binding site.

[0151] 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.

[0152] 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.

[0153] 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.

[0154] 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.

[0155] In addition, in the combination, two or more types of alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may be combined, and any of the groups may be bonded to a benzene ring.

[0156] R 3 , R 4 , R 5 and R 6 The -CH 2 - is -O-, -CO-, -NR 7 -, -S- or -SO 2 When it is replaced with -, the number of carbon atoms before the replacement is regarded as the total number of carbon atoms in the hydrocarbon group. In addition, the number may be 1 or 2 or more.

[0157] -CH contained in the hydrocarbon group 2 - is replaced by -O-, -CO-, -NR 7 -, -S- or -SO 2 - as the replaced group include a hydroxy group (-CH contained in the methyl group 2 - is replaced by -O-), an amino group (-CH contained in the methyl group 2 - is replaced by -NH-), a thiol group (-CH contained in the methyl group 2 - is replaced by -S-) a carboxy group (-CH contained in the ethyl group 2 -CH 2 - is replaced by -O-CO-), an alkoxy group (any position -CH contained in the alkyl group 2 - is replaced by -O-), an alkoxycarbonyl group (any position -CH contained in the alkyl group 2 -CH 2 - is replaced by -O-CO-), an alkylcarbonyl group (any position -CH contained in the alkyl group 2 - is replaced by -CO-), an alkylcarbonyloxy group (any position -CH contained in the alkyl group 2 -CH 2 - is replaced by -CO-O-), an alkylamino group (any position -CH contained in the alkyl group 2 - is replaced by -NR 7 -), an alkylthio group (any position -CH contained in the alkyl group 2 - is replaced by -S-), an alkylsulfonyl group (any position -CH contained in the alkyl group 2 - is replaced by -SO 2 -), an oxy group (-CH contained in the methylene group 2 - is replaced by -O-), a carbonyl group (-CH contained in the methylene group 2 - is replaced by -CO-), a thio group (-CH contained in the methylene group 2 - is replaced by -S-), a peptide group (-CH contained in the ethylene group 2 -CH 2 - is replaced by -CO-NR7 -replaced group), sulfonyl group (-CH contained in the methylene group 2 -is replaced by -SO 2 -replaced group), alkanediyl-oxy group (-CH at any position contained in the alkanediyl group 2 -is replaced by -O-), alkanediyl-oxycarbonyl group (-CH at any position contained in the alkanediyl group 2 -CH 2 -is replaced by -O-CO-), alkanediyl-carbonyl group (-CH at any position contained in the alkanediyl group 2 -is replaced by -CO-), alkanediyl-carbonyl-oxy group (-CH at any position contained in the alkanediyl group 2 -CH 2 -is replaced by -CO-O-), alkanediyl-amino group (-CH at any position contained in the alkanediyl group 2 -is replaced by -NR 7 -replaced group), alkanediyl-thio group (-CH at any position contained in the alkanediyl group 2 -is replaced by -S-), alkanediyl-sulfonyl group (-CH at any position contained in the alkanediyl group 2 -is replaced by -SO 2 -replaced group), cycloalkoxy group, cycloalkylalkoxy group, alkoxycarbonyloxy group, aromatic hydrocarbon group-carbonyl-oxy group, aromatic hydrocarbon group-carbonyl group, aromatic hydrocarbon group-oxy group, or a group formed by combining two or more of these groups, etc. may be mentioned.

[0158] Examples of the alkoxy group include alkoxy groups having 1 to 19 carbon atoms, such as 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 of the alkoxy group is preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0159] Examples of the alkoxycarbonyl group include alkoxycarbonyl groups having 2 to 19 carbon atoms, such as methoxycarbonyl group, ethoxycarbonyl group, butoxycarbonyl group and the like. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 20 carbon atoms, such as acetyl group, propionyl group and butyryl group. Examples of the alkylcarbonyloxy group include alkylcarbonyloxy groups having 2 to 19 carbon atoms, such as acetyloxy group, propionyloxy group, butyryloxy group and the like. The number of carbon atoms of the alkoxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms of the alkylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms of the alkylcarbonyloxy group is preferably 2 to 11, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3.

[0160] Examples of the alkylamino group include alkylamino groups having 1 to 19 carbon atoms, such as methylamino group, ethylamino group, propylamino group, butylamino group, pentylamino group, hexylamino group, octylamino group. The number of carbon atoms of the alkylamino group is preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0161] Examples of the alkylthio group include alkylthio groups having 1 to 19 carbon atoms, such as methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group, hexylthio group, octylthio group, 2-ethylhexylthio group, nonylthio group, decylthio group, undecylthio group and the like. The number of carbon atoms of the alkylthio group is preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0162] Examples of the alkylsulfonyl group include alkylsulfonyl groups having 1 to 19 carbon atoms, such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, octylsulfonyl group, 2-ethylhexylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, undecylsulfonyl group. The number of carbon atoms of the alkylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0163] Examples of the alkanediyl-oxy group include alkanediyl-oxy groups having 1 to 19 carbon atoms, such as methyleneoxy group, ethyleneoxy group, propanediyl-oxy group, butanediyl-oxy group, pentanediyl-oxy group and the like. The number of carbon atoms of the alkanediyl-oxy group is preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0164] Examples of the alkanediyl oxycarbonyl group include alkanediyl oxycarbonyl groups having 2 to 19 carbon atoms, such as a methylene oxycarbonyl group, an ethylene oxycarbonyl group, a propanediyl oxycarbonyl group, and a butanediyl oxycarbonyl group. Examples of the alkanediyl carbonyl group include alkanediyl carbonyl groups having 2 to 20 carbon atoms, such as a methylene carbonyl group, an ethylene carbonyl group, a propanediyl carbonyl group, a butanediyl carbonyl group, and a pentanediyl carbonyl group. Examples of the alkanediyl carbonyloxy group include alkanediyl carbonyloxy groups having 2 to 19 carbon atoms, such as a methylene carbonyloxy group, an ethylene carbonyloxy group, a propanediyl carbonyloxy group, and a butanediyl carbonyloxy group. The number of carbon atoms in the alkanediyl oxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkanediyl carbonyl group is preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkanediyl carbonyloxy group is preferably 2 to 11, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3.

[0165] Examples of the alkanediyl amino group include alkanediyl thio groups having 1 to 19 carbon atoms, such as a methylene amino group, an ethylene amino group, and a propylene amino group. The number of carbon atoms in the alkanediyl amino group is preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0166] Examples of the alkanediyl thio group include alkanediyl thio groups having 1 to 19 carbon atoms, such as a methylene thio group, an ethylene thio group, and a propylene thio group. The number of carbon atoms in the alkanediyl thio group is preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0167] Examples of the alkanediylsulfonyl group include alkanediylsulfonyl groups having 1 to 19 carbon atoms, such as methylenesulfonyl group, ethylenesulfonyl group, propylenesulfonyl group and the like. The number of carbon atoms of the alkanediylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0168] Examples of the cycloalkoxy group include cycloalkoxy groups having 3 to 19 carbon atoms, such as cyclohexyloxy group and the like. Examples of the cycloalkylalkoxy group include cycloalkylalkoxy groups having 4 to 19 carbon atoms, such as cyclohexylmethoxy group and the like. Examples of the alkoxycarbonyloxy group include alkoxycarbonyloxy groups having 2 to 18 carbon atoms, such as butoxycarbonyloxy group and the like. Examples of the aromatic hydrocarbon group-carbonyl-oxy group include aromatic hydrocarbon group-carbonyl-oxy groups having 7 to 19 carbon atoms, such as benzoyloxy group and the like. Examples of the aromatic hydrocarbon group-carbonyl group include aromatic hydrocarbon group-carbonyl groups having 7 to 20 carbon atoms, such as benzoyl group and the like. Examples of the aromatic hydrocarbon group-oxy group include aromatic hydrocarbon group-oxy groups having 6 to 19 carbon atoms, such as phenyloxy group and the like.

[0169] In addition, the -CH 2 - contained in the alicyclic hydrocarbon group is replaced by -O-, -CO-, -S-, -NR 7 - or -SO 2 - Examples of the resulting group include the groups represented below. The bonding site can be at any position.

[0170]

Chemical formula

[0171] R 7 The -CH contained in the hydrocarbon group represented by 2- is -O-, -CO-, -S- or -SO 2 - replaced groups are R 3 、R 4 、R 5 and R 6 -CH in the hydrocarbon group represented by 2 - is replaced by -O-, -CO-, -S- or -SO 2 - groups are the same as those exemplified.

[0172] R 3 and R 4 、R 5 and R 6 or R 3 and R 4 and R 5 - formed cyclic hydrocarbon groups are cyclic ammonium cations containing a nitrogen atom. -CH 2 - in the cyclic ammonium cation may be replaced by -O-, -CO- or -NR 7 - and -CH= in the cyclic ammonium cation may be replaced by -N=. Examples of the cyclic ammonium cation include monocyclic or polycyclic heterocyclic alicyclic hydrocarbon rings containing a nitrogen atom, cations derived from heterocyclic aromatic hydrocarbon rings containing a nitrogen atom, etc. Heterocyclic alicyclic hydrocarbon rings containing a nitrogen atom include pyrrolidine ring, imidazolidine ring, pyrazolidine ring, oxazolidine ring, isoxazolidine ring, pyridine ring, piperazine ring, morpholine ring, succinimide ring, 2-oxazolidone ring, quinuclidine ring, 1-azadamantane ring, etc. Heterocyclic aromatic hydrocarbon rings containing a nitrogen atom include pyrrole ring, pyrazole ring, imidazole ring, oxazole ring, imidazolidine ring, triazole ring, pyrazine ring, pyrimidine ring, indole ring, isoindole ring, quinoline ring, isoquinoline ring, carbazole ring, etc. Examples of the cyclic ammonium cation include ammonium cations represented below.

[0173] R 3 and R 4 、R 5 and R 6 or R 3and R 4 and R 5 The number of carbon atoms of the cyclic hydrocarbon group formed by the combination of each of them is preferably 3 to 12, and more preferably 4 to 12. R 3 and R 4 R 5 and R 6 or R 3 and R 4 and R 5 When they are combined to form a cyclic hydrocarbon group, for example, it is preferably a cyclic ammonium cation represented by the following formula.

[0174]

Chemical formula

[0175] R 3 and R 4 R 5 and R 6 or R 3 and R 4 and R 5 When they are combined to form a cyclic hydrocarbon group, other hydrocarbon groups such as a chain hydrocarbon group may be combined and may have a substituent.

[0176] R 3 R 4 R 5 R 6 and R 7 Examples of the substituent that the hydrocarbon groups of R, R, R, R, and R may have include a halogen atom, a cyano group, and a nitro group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0177] The hydrocarbon group may have one substituent or a plurality of substituents. R 3 R 4 R 5 and R 6is, independently, a hydrogen atom, a linear hydrocarbon group having 1 to 12 carbon atoms, a cyclic hydrocarbon group having 3 to 12 carbon atoms, or a group combining a linear hydrocarbon group having 1 to 8 carbon atoms and a cyclic hydrocarbon group having 3 to 12 carbon atoms, or R 3 and R 4 or R 3 and R 4 and R 5 and R 3 and R 4 or R 3 and R 4 and R 5 and R 2 - is preferably replaced by -O-, -S-, -NR 7 -, -SO 2 - or -CO-, and the linear hydrocarbon group, the cyclic hydrocarbon group and the alkyl group may have a substituent. Further, when each group combines to form a cyclic hydrocarbon group, the cyclic hydrocarbon group may form a double bond between one or more adjacent two carbon atoms, and -CH 2 - contained in the cyclic hydrocarbon group may be replaced by -O-, -CO- or -NR 7 -, and -CH= contained in the cyclic hydrocarbon group may be replaced by -N=.

[0178] In another aspect, R 3 , R 4 , R 5 and R 6 are each independently a hydrogen atom, an alkyl group having 1 to 9 carbon atoms, a phenyl group which may have a substituent, or an aralkyl group having 7 to 12 carbon atoms which may have a substituent (wherein -CH 2 - contained in the aralkyl group may be replaced by -O- or -CO-). R3 and R 4 When R is a hydrogen atom or an alkyl group having 1 to 9 carbon atoms, R 5 and R 6 At least one of them is a phenyl group which may have a substituent or an aralkyl group having 7 to 12 carbon atoms which may have a substituent (the -CH 2 - in the aralkyl group may be replaced by -O- or -CO-). It is preferable that

[0179] Also, in another aspect, R 3 and R 4 form a 5- or 6-membered alicyclic hydrocarbon group containing N + (the -CH 2 - in the alicyclic hydrocarbon group may be replaced by -O-), and R 5 and R 6 are each independently a hydrogen atom, an alkyl group having 1 to 9 carbon atoms, a phenyl group which may have a substituent or an aralkyl group having 7 to 12 carbon atoms which may have a substituent (the -CH 2 - in the aralkyl group may be replaced by -O- or -CO-). It is preferable that

[0180] Furthermore, in another aspect, R 3 and R 4 and R 5 form a 5- or 6-membered aromatic hydrocarbon group containing N + (the -CH= in the aromatic hydrocarbon group may be replaced by -N=), and R 6 is a hydrogen atom, an alkyl group having 1 to 9 carbon atoms, a phenyl group which may have a substituent or an aralkyl group having 7 to 12 carbon atoms which may have a substituent (the -CH 2 - in the aralkyl group may be replaced by -O- or -CO-). It is preferable that

[0181] R 7is preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, still more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and even more preferably a hydrogen atom or a methyl group.

[0182] Examples of the cation of the ammonium carboxylate salt (I) include cations represented by the following formulas (I-c-1) to (I-c-25).

[0183]

Chemical formula

[0184] The ammonium carboxylate salt (I-s) is a combination of the above-mentioned anion and the above-mentioned cation, and these can be arbitrarily combined. As the ammonium carboxylate salt (I-s), preferably, a combination of an anion represented by any of formulas (I-a-1) to (I-a-12), (I-a-32) to (I-a-36) and a cation represented by formulas (I-c-1) to (I-c-25) is mentioned.

[0185] Examples of the ammonium carboxylate salt (I-s) include the salts described in Table 1. In the following table, each symbol represents the symbol attached to the structure representing the above-mentioned anion or cation, and "~" indicates that each of the ammonium carboxylate salt (I-s) and the anion (I) corresponds. For example, the ammonium carboxylate salt (I-s-1) means a salt composed of an anion represented by formula (I-a-1) and a cation represented by formula (I-c-1), and represents the salt shown below.

[0186]

Chemical formula

[0187]

Table 1

[0188] Among them, the ammonium carboxylate salt (I-s) is preferably a salt formed by combining an anion represented by any of the formulas (I-a-1) to (I-a-12), (I-a-32) to (I-a-36) and a cation represented by any of the formulas (I-c-1) to (I-c-20).

[0189] <Structural unit (II)> The structural unit (II) is a structural unit having a group represented by the formula (II-x), and preferably a structural unit having a group represented by the formula (II-x) in the side chain.

[0190] [Chemical formula]

[0191] [In the formula (II-x), all symbols have the same meanings as described above.] Ring W 1 represents a ring structure in which, as an atom constituting the ring, it contains a nitrogen atom and one of the carbon atoms constituting the ring forms a carbonyl group together with an oxo group (=O).

[0192] Ring W 1 The heterocyclic ring of may be further replaced, for example, by -CH 2 - being replaced by -O-, -S-, -CO- or -NR c - group or the like. R c represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. The heterocyclic ring of Ring W 1 may be an aromatic heterocyclic ring or an alicyclic heterocyclic ring having no aromaticity. It may be either monocyclic or polycyclic.

[0193] As the group represented by the following formula (II-x1), which is a part of the group represented by the formula (II-x), specifically, the following may be mentioned. * represents the bonding site to the carbon atom of the carbonyl group.

[0194] [Chemistry]

[0195] [Chemistry]

[0196] Ring W 1 The hydrogen atoms contained in the heterocyclic ring having 2 to 36 carbon atoms represented by may be halogen atoms or hydrocarbon groups having 1 to 24 carbon atoms (the -CH 2 - in may be replaced by -O-, -S-, -CO- or -NR c - group).) may be substituted.

[0197] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like. Examples of the hydrocarbon group include an aliphatic hydrocarbon group, an aromatic hydrocarbon group, and a group combining these. The -CH 2 - in may be -O-, -S-, -CO-, -NR c - group (R c represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.) may be replaced, and it is preferably replaced by -O- or -CO-.

[0198] The aliphatic hydrocarbon group represents a chain hydrocarbon group, an alicyclic hydrocarbon group, and a group combining a chain hydrocarbon group and an alicyclic hydrocarbon group. The chain hydrocarbon group may be saturated or unsaturated, and may be linear or branched. For example, linear saturated alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, octyl group, decyl group, dodecyl group, pentadecyl group and hexadecyl group; branched saturated alkyl groups such as isopropyl group, sec-butyl group, tert-butyl group and 2-ethylhexyl group; linear unsaturated alkyl groups such as vinyl group, propenyl group, hexenyl group and octenyl group; and branched unsaturated alkyl groups such as 3-methyl-2-butenyl group.

[0199] The number of carbon atoms in the chain hydrocarbon group is preferably from 1 to 12, more preferably from 1 to 10, still more preferably from 1 to 8, even more preferably from 1 to 6, and even still more preferably from 1 to 4.

[0200] The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include monocyclic cycloalkyl groups such as cyclopentyl group, cyclohexyl group, methylcyclohexyl group, dimethylcyclohexyl group, cycloheptyl group, and cyclooctyl group. Examples of the polycyclic alicyclic hydrocarbon group include polycyclic cycloalkyl groups such as decahydronaphthyl group, adamantyl group, norbornyl group, methylnorbornyl group, and groups as follows.

[0201]

Chemical formula

[0202] The number of carbon atoms in the alicyclic hydrocarbon group is preferably from 3 to 18, more preferably from 3 to 16, and still more preferably from 3 to 12. Examples of the group formed by combining the chain hydrocarbon group and the alicyclic hydrocarbon group include groups formed by bonding the above-mentioned chain hydrocarbon group and the above-mentioned alicyclic hydrocarbon group, groups formed by bonding the above-mentioned alicyclic hydrocarbon group and the above-mentioned chain hydrocarbon group, and groups formed by bonding the above-mentioned chain hydrocarbon group, the above-mentioned alicyclic hydrocarbon group, and the above-mentioned chain hydrocarbon group, etc., within the range allowed by the upper limit of the number of carbon atoms.

[0203] Examples of the aromatic hydrocarbon group include phenyl group, naphthyl group, anthryl group, etc. The number of carbon atoms in the aromatic hydrocarbon group is preferably from 6 to 18, more preferably from 6 to 14, and still more preferably from 6 to 10.

[0204] Examples of a group combining an aliphatic hydrocarbon group and an aromatic hydrocarbon group include, within the range allowed by the upper limit of the number of carbon atoms, for example, a group formed by bonding the above-described chain hydrocarbon group and the above-described aromatic hydrocarbon group, a group formed by bonding the above-described aromatic hydrocarbon group and the above-described chain hydrocarbon group, a group formed by bonding the above-described aromatic hydrocarbon group and the above-described alicyclic hydrocarbon group via a single bond or the above-described chain hydrocarbon group, and the like.

[0205] -CH contained in the hydrocarbon group 2 - is replaced by -O-, -S-, -CO- or -NR c Examples of the group thus replaced include a hydroxy group, a carboxy group, an alkoxy group, an alkylcarbonyl group, an alkylcarbonyloxy group, an alkylthio group, an amino group, a thiol group, an alkoxycarbonyl group, an alkylsulfonyl group, and an alkylamino group.

[0206] 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. The number of carbon atoms in the alkoxy group is, for example, 1 to 12, preferably 1 to 8, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0207] Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, and a butyryl group. The number of carbon atoms in the alkylcarbonyl group is, for example, 2 to 12, preferably 2 to 8, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 to 3.

[0208] Examples of the alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, a butyryloxy group, and an isobutyryloxy group. The number of carbon atoms in the alkylcarbonyloxy group is, for example, 2 to 12, preferably 2 to 8, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 to 3.

[0209] Examples of the alkylthio group include a methylthio group, an ethylthio group, a propylthio group, a butylthio group and the like. The number of carbon atoms in the alkylthio group is 1 to 12, preferably 1 to 8, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0210] Examples of the alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a butoxycarbonyl group and the like. The number of carbon atoms in the alkoxycarbonyl group is 2 to 12, preferably 2 to 8, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 to 3.

[0211] Examples of the alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, an octylsulfonyl group, a nonylsulfonyl group, a decylsulfonyl group, an undecylsulfonyl group and the like. The number of carbon atoms in the alkylsulfonyl group is 1 to 12, preferably 1 to 8, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0212] Examples of the alkylamino group include a methylamino group, an ethylamino group, a propylamino group, a butylamino group and the like. The number of carbon atoms in the alkylamino group is 1 to 12, preferably 1 to 8, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0213] Ring W 1is preferably a 4- to 12-membered heterocyclic ring containing a nitrogen atom or a heterocyclic ring containing the 4- to 12-membered ring, more preferably a 4- to 7-membered heterocyclic ring containing a nitrogen atom or a heterocyclic ring containing the 4- to 7-membered ring, still more preferably a 4- to 6-membered heterocyclic ring containing a nitrogen atom or a heterocyclic ring containing the 4- to 6-membered ring, and even more preferably a 4- to 6-membered heterocyclic ring containing a nitrogen atom or a polycyclic structure containing the 4- to 6-membered heterocyclic ring. -CO- is arranged at a position adjacent to the nitrogen atom, that is, ring W 1 is preferably a lactam ring, and more preferably a lactam ring having a polycyclic structure.

[0214] Ring W 1 When a hydrogen atom contained in the heterocyclic ring of Ring W is replaced with a halogen atom, a hydrocarbon group, etc., it is preferably substituted with a halogen atom, a hydroxy group, an alkoxy group having 1 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, or an alkylcarbonyloxy group having 2 to 4 carbon atoms, and more preferably substituted with an iodine atom, a fluorine atom, a hydroxy group, an alkylcarbonyl group having 2 to 4 carbon atoms, or an alkylcarbonyloxy group having 2 to 4 carbon atoms.

[0215] The structural unit having the group represented by formula (II-x) has a group derived from a polymerizable group. Examples of the polymerizable group include a vinyl group, an acryloyl group, a methacryloyl group, an acryloyloxy group, a methacryloyloxy group, an acryloylamino group, a methacryloylamino group, an acryloylthio group, a methacryloylthio group, and the like.

[0216] Among them, the monomer that leads to structural unit (II) is preferably a monomer having an ethylenically unsaturated bond, and more preferably a (meth)acrylic monomer. Structural unit (II) is preferably a structural unit represented by formula (IIA).

[0217]

Chemical formula

[0218] [In formula (IIA), all symbols have the same meanings as described above.] R x Examples of the halogen atom of R include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0219] R x Examples of the alkyl group of R include, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, and an n-hexyl group, etc. Preferably, it is an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group.

[0220] R x Examples of the alkyl group having a halogen atom of R include, for example, 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, etc.

[0221] R x is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group. A X1 Examples of the divalent saturated hydrocarbon group of A include a chain saturated hydrocarbon group such as a linear or branched alkanediyl group, a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, and those obtained by combining two or more of these groups may also be used.

[0222] Specifically, linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, tridecane-1,13-diyl group, tetradecane-1,14-diyl group, pentadecane-1,15-diyl group, hexadecane-1,16-diyl group, heptadecane-1,17-diyl group, ethane-1,1-diyl group, propane-1,1-diyl group and propane-2,2-diyl group; branched alkanediyl groups such as butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group; monocyclic divalent alicyclic saturated hydrocarbon groups which are cycloalkanediyl groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclooctane-1,5-diyl group; polycyclic divalent alicyclic saturated hydrocarbon groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, etc. are included.

[0223] The number of carbon atoms in the chain saturated hydrocarbon group is preferably 1 to 12, more preferably 1 to 8, still more preferably 1 to 6, and even more preferably 1 to 4. The number of carbon atoms in the alicyclic saturated hydrocarbon group is preferably 3 to 16, more preferably 3 to 12, and still more preferably 3 to 10.

[0224] -CH 2 - in the saturated hydrocarbon group is -O-, -CO- or -NR d-The groups replacing - include hydroxy group, carboxy group, amino group, alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, alkylcarbonyloxy group, alkylamino group, oxy group, carbonyl group, alkanedioxy group, alkanedioxycarbonyl group, alkanediylcarbonyl group, alkanediylcarbonyloxy group, alkanediylamino group, and -CH contained in an alicyclic saturated hydrocarbon group 2 -is replaced by -O-, -CO- or -NR d -, groups formed by combining two or more of these groups, and the like. These replaced groups include the same groups as those exemplified in this specification within the range where the upper limit of the number of carbon atoms permits.

[0225] A X1 is an alkanediyl group having 1 to 6 carbon atoms (in the alkanediyl group, -CH 2 - may be replaced by -O-, -CO- or -N(R d ))). An alkanediyl group having 1 to 4 carbon atoms (in the alkanediyl group, -CH 2 - may be replaced by -O-, -CO- or -N(R d ))). is more preferable.

[0226] A X is a single bond, -CO-O-(CH 2 ) gg -*, -CO-NH-(CH 2 ) gg -*, -CO-O-(CH 2 ) gg -O-* (* represents the bonding site with the carbonyl group. gg represents any integer from 1 to 4). is preferable, a single bond, -CO-O-(CH 2 ) gg -* (* represents the bonding site with the carbonyl group. gg represents any integer from 1 to 4). is more preferable, and a single bond is even more preferable.

[0227] Examples of the structural unit (II) include the following structural units.

[0228]

Chem.

[0229]

Chem.

[0230] In the structural units represented by Formula (II-1) to Formula (II-10), the structural units in which the methyl group corresponding to R X is replaced by a hydrogen atom can also be cited as specific examples of the structural unit (II). Among them, the structural units represented by Formula (II-1), Formula (II-6) to Formula (II-9) are preferred, and the structural units represented by Formula (II-1) and Formula (II-7) are more preferred.

[0231] The resin (A) may be a copolymer containing one structural unit represented by Formula (I) and two or more structural units represented by Formula (II), or a copolymer containing two or more structural units represented by Formula (I) and one structural unit represented by Formula (II), or a copolymer containing two or more structural units represented by Formula (I) and two or more structural units represented by Formula (II).

[0232] The content of the structural unit represented by Formula (I) is 0.1 mol% or more, preferably 0.5 mol% or more, more preferably 0.8 mol% or more, still more preferably 1 mol% or more, even more preferably 3 mol% or more, still even more preferably 5 mol% or more, and yet even more preferably 7 mol% or more, based on all the structural units of the resin (A). Also, it is 30 mol% or less, preferably 25 mol% or less, more preferably 20 mol% or less, still more preferably 15 mol% or less. Specifically, it is 0.1 to 30 mol%, preferably 0.5 to 25 mol%, more preferably 0.8 to 20 mol%, and still more preferably 1 to 15 mol%.

[0233] The content rate of the structural unit represented by the formula (II) is 0.1 mol% or more, preferably 0.5 mol% or more, more preferably 0.8 mol% or more, still more preferably 1 mol% or more, even more preferably 3 mol% or more, still even more preferably 5 mol% or more, and yet still even more preferably 7 mol% or more, based on all the structural units of the resin (A). Also, it is 60 mol% or less, preferably 50 mol% or less, more preferably 40 mol% or less, still more preferably 30 mol% or less, even more preferably 25 mol% or less, still even more preferably 20 mol% or less, and yet still even more preferably 15 mol% or less. Specifically, it is 1 to 60 mol%, preferably 3 to 50 mol%, more preferably 5 to 40 mol%, still more preferably 5 to 30 mol%, even more preferably 5 to 25 mol%, still even more preferably 5 to 20 mol%, and yet still even more preferably 5 to 15 mol%.

[0234] [Structural units other than structural unit (I) and structural unit (II)] The resin (A) may further contain structural units other than the structural unit (I) and the structural unit (II).

[0235] Examples of the structural units other than the structural unit (I) and the structural unit (II) include structural units having an acid-labile group (hereinafter sometimes referred to as "structural unit (a1)"), structural units not having an acid-labile group (hereinafter sometimes referred to as "structural unit (s)"), and structural units known in the art, etc.

[0236] 〈Structural unit (a1)〉 The structural unit (a1) is derived from a monomer having an acid-labile group (hereinafter sometimes referred to as "monomer (a1)").

[0237] The acid-labile group contained in the resin (A) is preferably a group represented by the formula (1) (hereinafter also referred to as "group (1)") and / or a group represented by the formula (2) (hereinafter also referred to as "group (2)").

[0238] [Chemical formula]

[0239] [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 these, or R a1 and R a2 are bonded to each other to form an alicyclic hydrocarbon group having 3 to 20 carbon atoms together with the carbon atom to which they are bonded, and the alkyl group, the alkenyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may have a halogen atom.

[0240] ma and na each independently represent 0 or 1, and at least one of ma and na represents 1. * represents a bonding site.]

[0241]

Chemical formula

[0242] [In formula (2), R a1′ and R a2′ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, R a3′ represents a hydrocarbon group having 1 to 20 carbon atoms, or R a2′ and R a3′ are bonded to each other to form a heterocyclic group having 3 to 20 carbon atoms together with the carbon atom to which they are bonded and X, and -CH 2 - contained in the hydrocarbon group and the heterocyclic group may be replaced by -O- or -S-, and the hydrocarbon group and the heterocyclic group may have a halogen atom.

[0243] X represents an oxygen atom or a sulfur atom. na′ represents 0 or 1. * represents a bonding site.] R a1 , R a2 and R a3Examples 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.

[0244] R a1 , R a2 and R a3 Examples of the alkenyl group in include an ethenyl group, a propenyl group, an isopropenyl group, a butenyl group, an isobutenyl group, a tert-butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, an isooctenyl group, and a nonenyl group.

[0245] 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). R a1 , R a2 and R a3 The alicyclic hydrocarbon group preferably has 3 to 16 carbon atoms.

[0246] [ka]

[0247] R a1 , R a2 and R a3 Examples of the aromatic hydrocarbon group in 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 formed by combining the above-described alkyl group and alicyclic hydrocarbon group (e.g., an alkylcycloalkyl group or cycloalkylalkyl group such as methylcyclohexyl group, dimethylcyclohexyl group, methylnorbornil group, cyclohexylmethyl group, adamantylmethyl group, adamantyldimethyl group, norbornylethyl group, etc.), an aralkyl group such as benzyl group, an aromatic hydrocarbon group having an alkyl group (p-methylphenyl group, p-tert-butylphenyl group, tolyl group, xylyl group, cumenyl group, mesityl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group, etc.), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (p-cyclohexylphenyl group, p-adamantylphenyl group, etc.), an aryl-cycloalkyl group such as phenylcyclohexyl group, and the like.

[0248] Preferably, ma is 0 and na is 1. R a1 and R a2 When they are bonded to each other to form an alicyclic hydrocarbon group, examples of -C(R a1 )(R a2 )(R a3 ) include the following groups. The alicyclic hydrocarbon group preferably has 3 to 12 carbon atoms. * represents the bonding site with -O-.

[0249]

Chemical formula

[0250] R a1′ 、R a2′ and R a3′ Examples of the hydrocarbon group in include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these.

[0251] The alkyl group, alicyclic hydrocarbon group, aromatic hydrocarbon group, and the group formed by combining these are the same as the groups exemplified for R a1 、R a2 and R a3 . R a2′ and R a3′ When they are bonded to each other to form a heterocyclic group together with the carbon atom to which they are bonded and X, -C(R a1′ )(R a2′ )-X-R a3′ Examples of this include the following groups. * represents the bonding site.

[0252] [Chemical formula]

[0253] R a1′ and R a2′ It is preferable that at least one of them is a hydrogen atom. na′ is preferably 0. R a1 , R a2 , R a3 , R a1 , R a2′ and R a3′ Examples of the halogen atom that R

[0254] Examples of group (1) include the following groups. In formula (1), R a1 , R a2 and R a3 are alkyl groups, ma = 0, and na = 1. Preferred examples of this group include the tert-butoxycarbonyl group.

[0255] In formula (1), R a1 , R a2 together with the carbon atom to which they are bonded form an adamantyl group, 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, R a3 is an adamantyl group, ma = 0, and na = 1.

[0256] Examples of the group (1) specifically include the following groups. * represents the bonding site.

[0257] [Chemical formula]

[0258] [Chemical formula]

[0259] Specific examples of the group (2) include the following groups. * represents the bonding site.

[0260] [Chemical formula]

[0261] 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. Among the (meth)acrylic monomers having an acid-labile group, preferably those having an alicyclic hydrocarbon group with 5 to 20 carbon atoms are mentioned. If 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 the resist composition, the resolution of the resist pattern can be improved.

[0262] As a structural unit derived from a (meth)acrylic monomer having a group (1), there are a structural unit represented by the formula (a1-0) (hereinafter, may be referred to as structural unit (a1-0)), a structural unit represented by the formula (a1-1) (hereinafter, may be referred to as structural unit (a1-1)), or a structural unit represented by the formula (a1-2) (hereinafter, may be referred to as structural unit (a1-2)). Preferably, it is at least one structural unit selected from the group consisting of structural unit (a1-0), structural unit (a1-1), and structural unit (a1-2), and more preferably, it is 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.

[0263] [Chemical formula]

[0264] [In formula (a1-0), formula (a1-1), and formula (a1-2), L a01 、L a1 and L a2 each independently represents -O- or *-O-(CH 2 ) k1 -CO-O-, k1 represents an integer from 1 to 7, and * represents the bonding site with -CO-.

[0265] R a01 、R a4 and R a5 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a02 、R a03 and R a04 each independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these, and the alkyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may have a halogen atom.

[0266] R a6 and Ra7 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, the alkenyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may have a halogen atom.

[0267] m1′ represents any integer from 0 to 14. n1 represents any integer from 0 to 10. n1′ represents any integer from 0 to 3. R a01 、R a4 and R a5 Examples of the halogen atom in are a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0268] R a01 、R a4 and R a5 Examples of the alkyl group that may have a halogen atom in are 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 of 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.

[0269] R a01 、R a4 and R a5 are preferably a hydrogen atom or a methyl group, and more preferably a methyl group. L a01 、La1 and L a2 is preferably an oxygen atom or *-O-(CH 2 ) k01 -CO-O- (where k01 is preferably any integer from 1 to 4, more preferably 1), and more preferably an oxygen atom.

[0270] R a02 , R a03 , R a04 , R a6 and R a7 Examples of the alkyl group, alkenyl group, alicyclic hydrocarbon group, aromatic hydrocarbon group, and groups combining these in R a1 , R a2 and R a3 are the same as the groups exemplified by R

[0271] R a02 , R a03 , and R a04 The alkyl group in 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.

[0272] R a6 and R a7 The alkyl group in 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.

[0273] R a6 and R a7 The alkenyl group in is preferably an alkenyl group having 2 to 6 carbon atoms, more preferably an ethenyl group, a propenyl group, an isopropenyl group, or a butenyl group.

[0274] R a02 , R a03 , R a04 , R a6 and R a7 The number of carbon atoms of the alicyclic hydrocarbon group of is preferably 5 to 12, and more preferably 5 to 10. R a02 、R a03 、R a04 、R a6 and R a7 The number of carbon atoms of the aromatic hydrocarbon group of R is preferably 6 to 12, more preferably 6 to 10.

[0275] For the group combining an alkyl group and an alicyclic hydrocarbon group, it is preferable that the total number of carbon atoms of these alkyl group and alicyclic hydrocarbon group is 18 or less. For the group combining an alkyl group and an aromatic hydrocarbon group, it is preferable that the total number of carbon atoms of these alkyl group and aromatic hydrocarbon group is 18 or less.

[0276] R a02 and R a03 are 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, more preferably a methyl group, an ethyl group, a phenyl group or a naphthyl group which may have a halogen atom.

[0277] 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, more preferably a methyl group, an ethyl group, a cyclohexyl group or an adamantyl group which may have a halogen atom.

[0278] R a6 and R a7 are 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, an ethyl group, an isopropyl group, a t-butyl group, an ethenyl group, a phenyl group or a naphthyl group which may have a halogen atom, still more preferably an ethyl group, an isopropyl group, a t-butyl group, an ethenyl group or a phenyl group which may have a halogen atom.

[0279] m1′ is preferably any integer from 0 to 3, more preferably 0 or 1. n1 is preferably any integer from 0 to 3, more preferably 0 or 1.

[0280] n1′ is preferably 0 or 1. Examples of the structural unit (a1-0) include structural units represented by any of formula (a1-0-1) to formula (a1-0-24) and structural units in which the methyl group corresponding to R in the structural unit (a1-0) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group (an alkyl group having a halogen atom), or another alkyl group. Structural units represented by any of formula (a1-0-1) to formula (a1-0-10), formula (a1-0-13), formula (a1-0-14), formula (a1-0-19) to formula (a1-0-24) are preferred. a01 Examples of the structural unit (a1-0) include structural units represented by any of formula (a1-0-1) to formula (a1-0-24) and structural units in which the methyl group corresponding to R in the structural unit (a1-0) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group (an alkyl group having a halogen atom), or another alkyl group. Structural units represented by any of formula (a1-0-1) to formula (a1-0-10), formula (a1-0-13), formula (a1-0-14), formula (a1-0-19) to formula (a1-0-24) are preferred.

[0281] [Chemical formula]

[0282] Examples of the structural unit (a1-1) include structural units derived from the monomers described in JP-A-2010-204646. Among them, structural units represented by any of formula (a1-1-1) to formula (a1-1-7) and structural units in which the methyl group corresponding to R in the structural unit (a1-1) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group are preferred, and structural units represented by any of formula (a1-1-1) to formula (a1-1-4) are more preferred. a4 Examples of the structural unit (a1-1) include structural units derived from the monomers described in JP-A-2010-204646. Among them, structural units represented by any of formula (a1-1-1) to formula (a1-1-7) and structural units in which the methyl group corresponding to R in the structural unit (a1-1) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group are preferred, and structural units represented by any of formula (a1-1-1) to formula (a1-1-4) are more preferred.

[0283] [Chemical formula]

[0284] Examples of the structural unit (a1-2) include structural units represented by any of formula (a1-2-1) to formula (a1-2-20) and structural units in which the methyl group corresponding to R in the structural unit (a1-2) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group. a5Examples of the structural unit in which the methyl group corresponding to the formula is replaced with a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group include structural units represented by any of formula (a1-2-2), formula (a1-2-5), formula (a1-2-6), and formula (a1-2-10) to formula (a1-2-20).

[0285]

Chemical formula

[0286] 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 thereof is 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, still more preferably 25 mol% or more, even more preferably 30 mol% or more, still even more preferably 40 mol% or more, and even more preferably 50 mol% or more, based on all the structural units of the resin (A). Further, it is 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, still more preferably 70 mol% or less, even more preferably 65 mol% or less. Specifically, it is 10 to 95 mol%, preferably 15 to 90 mol%, more preferably 20 to 85 mol%, still more preferably 25 to 70 mol%, and even more preferably 30 to 70 mol%.

[0287] When the resin (A) contains the structural unit (a1-0), its content is 5 mol% or more, preferably 10 mol% or more, more preferably 15 mol% or more, still more preferably 20 mol% or more, even more preferably 25 mol% or more, still even more preferably 30 mol% or more, and even more preferably 35 mol% or more, based on all the structural units of the resin (A). Also, it is 80 mol% or less, preferably 75 mol% or less, more preferably 70 mol% or less, still more preferably 65 mol% or less, even more preferably 60 mol% or less. Specifically, it is 5 to 80 mol%, preferably 5 to 75 mol%, and more preferably 10 to 70 mol%.

[0288] When the resin (A) contains the structural unit (a1-1) and / or the structural unit (a1-2), their total content is 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, still more preferably 25 mol% or more, even more preferably 30 mol% or more, still even more preferably 40 mol% or more, and even more preferably 50 mol% or more, based on all the structural units of the resin (A). Also, it is 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, still more preferably 80 mol% or less, even more preferably 75 mol% or less, still even more preferably 70 mol% or less, and even more preferably 65 mol% or less. Specifically, it is 10 to 95 mol%, preferably 15 to 85 mol%, more preferably 15 to 80 mol%, still more preferably 20 to 80 mol%, even more preferably 20 to 75 mol%, still even more preferably 20 to 70 mol%, and even more preferably 20 to 55 mol%.

[0289] Examples of the structural unit having the group (2) in the structural unit (a1) include the structural unit represented by the formula (a1-4) (hereinafter sometimes referred to as "structural unit (a1-4)").

[0290]

Chemical formula

[0291] [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.

[0292] 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.

[0293] A a11 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and -CH 2 - contained in the alkanediyl group may be replaced by -O-, -CO- or -NR a18 -.

[0294] 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 represent 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 -CH 2 - contained in the hydrocarbon group and the divalent hydrocarbon group may be replaced by -O- or -S-.

[0295] na1 represents any integer from 1 to 5. When na1 is 2 or more, the groups within the plurality of parentheses may be the same as or different from each other. na11 represents any integer from 0 to 4. When na11 is 2 or more, the plurality of Rs a17 may be the same as or different from each other.

[0296] mc represents any integer from 0 to 2. R a1 and R a17 Examples of the halogen atom in R and R include a fluorine atom, a chlorine atom, and a bromine atom.

[0297] R a1 and R a17 Examples of the alkyl group having 1 to 6 carbon atoms that may have a halogen atom in R and R 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 of 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.

[0298] 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 still more preferably a hydrogen atom or a methyl group. R a17Examples of the alkoxy group in [compound name] include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, and hexyloxy group. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably an alkoxy group having 1 to 3 carbon atoms, still more preferably a methoxy group or an ethoxy group, and even more preferably a methoxy group.

[0299] R a17 Examples of the alkoxyalkyl group in [compound name] include methoxymethyl group, ethoxyethyl group, propoxymethyl group, isopropoxymethyl group, butoxymethyl group, sec-butoxymethyl group, and tert-butoxymethyl group. The alkoxyalkyl group is preferably an alkoxyalkyl group having 2 to 8 carbon atoms, more preferably an alkoxyalkyl group having 2 to 4 carbon atoms, still more preferably a methoxymethyl group or an ethoxyethyl group, and even more preferably a methoxymethyl group.

[0300] R a17 Examples of the alkoxyalkoxy group in [compound name] include methoxymethoxy group, methoxyethoxy group, ethoxymethoxy group, ethoxyethoxy group, propoxymethoxy group, isopropoxymethoxy group, butoxymethoxy group, sec-butoxymethoxy group, and tert-butoxymethoxy group. The alkoxyalkoxy group is preferably an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably an alkoxyalkoxy group having 2 to 4 carbon atoms, still more preferably a methoxyethoxy group or an ethoxyethoxy group.

[0301] R a17 Examples of the alkylcarbonyl group in [compound name] include acetyl group, propionyl group, and butyryl group. The alkylcarbonyl group is preferably an alkylcarbonyl group having 2 to 4 carbon atoms, more preferably an alkylcarbonyl group having 2 to 3 carbon atoms, still more preferably an acetyl group.

[0302] R a17Examples of the alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, and a butyryloxy group. The alkylcarbonyloxy group is preferably an alkylcarbonyloxy group having 2 to 4 carbon atoms, more preferably an alkylcarbonyloxy group having 2 to 3 carbon atoms, and even more preferably an acetyloxy group.

[0303] R a17 is preferably a halogen atom, a hydroxy group, a carboxy group, an optionally halogenated 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.

[0304] A a11 Examples of the alkanediyl group of A include linear alkanediyl groups such as 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 heptane-1,7-diyl group, an octane-1,8-diyl group, a nonane-1,9-diyl group, a decane-1,10-diyl group, an undecane-1,11-diyl group, and a dodecane-1,12-diyl group, and branched alkanediyl groups such as 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, a 2-methylbutane-1,4-diyl group, a heptane-1,6-diyl group, an octane-1,7-diyl group, a nonane-1,8-diyl group, a decane-1,9-diyl group, and an undecane-1,10-diyl group. The number of carbon atoms of 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, yet more preferably 1 to 3, and even more preferably 1 or 2.

[0305] R a18Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, and a tert-butyl group. A a11 When -CH 2 - included in the alkanediyl group of is replaced with -O-, -CO- or -NR a18 -, the number of carbon atoms before replacement is defined as the number of carbon atoms of the alkanediyl group.

[0306] A a11 Examples of the group in which -CH 2 - included in the alkanediyl group of is replaced with -O-, -CO- or -NR a18 - include a hydroxy group (a group in which -CH 2 - included in the methyl group is replaced with -O-), a carboxy group (a group in which -CH 2 -CH 2 - included in the ethyl group is replaced with -O-CO-), a carbonyl group (a group in which -CH 2 - included in the methylene group is replaced with -CO-), an oxy group (a group in which -CH 2 - included in the methylene group is replaced with -O-), an amino group (a group in which -CH 2 - included in the methyl group is replaced with -NR a18 -), an alkoxy group (a group in which -CH 2 - at any position included in the alkyl group is replaced with -O-), an alkoxycarbonyl group (a group in which -CH 2 -CH 2 - at any position included in the alkyl group is replaced with -O-CO-), an alkylcarbonyl group (a group in which -CH 2 - at any position included in the alkyl group is replaced with -CO-), an alkylamino group (a group in which -CH 2 - at any position included in the alkyl group is replaced with -NR a18 -), a peptide group (a group in which -CH 2 -CH 2 - included in the ethylene group is replaced with -CO-NR a18 -), and an alkanediyl-oxy group (a group in which -CH 2- is a group replaced by -O-, an alkanediyl oxycarbonyl group (any -CH at any position contained in the alkanediyl group) 2 -CH 2 - is a group replaced by -O-CO-, an alkanediyl carbonyl group (any -CH at any position contained in the alkanediyl group) 2 - is a group replaced by -CO-, an alkanediyl carbonyl oxy group (any -CH at any position contained in the alkanediyl group) 2 -CH 2 - is a group replaced by -CO-O-, an alkanediyl sulfonyl group (any -CH at any position contained in the alkanediyl group) 2 - is replaced by -SO 2 - is a group replaced by -SO-, an alkanediyl thio group (any -CH at any position contained in the alkanediyl group) 2 - is a group replaced by -S-, an alkanediyl amino group (any -CH at any position contained in the alkanediyl group) 2 - is replaced by -NR a18 - is a group replaced by -NR-, etc. These replaced groups include those similar to the examples illustrated in this specification within the range permitted by the upper limit of the number of carbon atoms.

[0307] Examples of the alkylamino group include alkylamino groups having 1 to 11 carbon atoms, such as methylamino group, ethylamino group, propylamino group, butylamino group, pentylamino group, hexylamino group, octylamino group, etc. The number of carbon atoms of the alkylamino group is preferably 1 to 8, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0308] Examples of the alkanediylamino group include alkanediylamino groups having 1 to 11 carbon atoms, such as methyleneamino group, ethyleneamino group, propyleneamino group, etc. The number of carbon atoms of the alkanediylamino group is preferably 1 to 8, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0309] For example, Aa11 The -CH contained in the alkanediyl group of 2 - is replaced by -O-, -CO-, or -NR a18 - The groups thus replaced include *-O-, *-CO-O-, *-O-CO-, *-CO-O-A a12 -CO-O-, *-O-CO-A a12 -O-, *-O-A a12 -CO-O-, *-CO-O-A a12 -O-CO-, *-O-CO-A a12 -O-CO-, *-CO-NR a18 - are mentioned. Among them, *-CO-O-, *-CO-O-A a12 -CO-O-, *-O-A a12 -CO-O-, *-CO-NR a18 - are preferred. Here, A a12 represents an alkanediyl group having 1 to 8 carbon atoms, and * represents the bonding site with the carbon atom to which R a1 is bonded. The alkanediyl group of A a12 includes alkanediyl groups similar to A a11 within the range allowed by the upper limit of the number of carbon atoms.

[0310] A a11 is preferably a single bond, *-CO-O-, or *-CO-O-A a12 -CO-O-, more preferably a single bond, *-CO-O-, or *-CO-O-CH 2 -CO-O-, and even more preferably a single bond or *-CO-O-.

[0311] 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.

[0312] mc is preferably 0 or 1. R a34 、R a35 and R a36Examples of the hydrocarbon group in [the compound] include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these groups.

[0313] 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, an octyl group, and the like. The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include cycloalkyl groups such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. Examples of the polycyclic alicyclic hydrocarbon group include a decahydronaphthyl group, an adamantyl group, a norbornyl group, and the following group (* represents a bonding site), and the like.

[0314] [Chemical formula]

[0315] 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 formed by combining the above-described alkyl group and alicyclic hydrocarbon group (for example, an alkylcycloalkyl group or a cycloalkylalkyl group such as a methylcyclohexyl group, a dimethylcyclohexyl group, a methylnorbornyl group, a cyclohexylmethyl group, an adamantylmethyl group, an adamantyldimethyl group, and 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, etc.), an aromatic hydrocarbon group having an alicyclic hydrocarbon group (a p-cyclohexylphenyl group, a p-adamantylphenyl group, etc.), an aryl-cycloalkyl group such as a phenylcyclohexyl group, and the like. In particular, R a36 includes 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.

[0316] R a35 and R a36 Examples of the divalent hydrocarbon group having 2 to 20 carbon atoms formed by combining with each other together with -C-O- to which they are attached include the following groups. * represents a bonding site, and one side is the bonding site with R a34 and the other side is the bonding site with R

[0317] [Chemical formula]

[0318] 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

[0319] R a36 The hydrocarbon group of 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. The alkyl group and alicyclic hydrocarbon group in R a36 are preferably unsubstituted. The aromatic hydrocarbon group in R a36 preferably has an aromatic ring having an aryloxy group having 6 to 10 carbon atoms

[0320] -O-C(R a34 )(R a35 )-O-R a36 in the structural unit (a1-4) eliminates upon contact with an acid (e.g., p-toluenesulfonic acid) to form a hydroxy group or a carboxy group

[0321] -X a1 -O-C(R a34 )(R a35 )-O-R a36In the case of a benzene ring, A a11 may be bonded to any of the o-position, m-position or p-position with respect to the bonding position. Among them, it is preferable that at least one is bonded to the o-position or p-position, and more preferably bonded to the p-position. In the case of a naphthalene ring, when the bonding position of A a11 is at the 1-position, it may be bonded to any of the 2nd to 8th positions. When the bonding position of A a11 is at the 2-position, it may be bonded to any of the 1st and 3rd to 8th positions. Among them, when the bonding position of A a11 is at the 1-position, it is preferable that at least one is bonded to the 3rd to 6th positions, and more preferably bonded to the 3rd or 4th position. When the bonding position of A a11 is at the 2-position, it is preferable that it is bonded to the 4th to 7th positions, and more preferably bonded to the 5th or 6th position.

[0322] Examples of the structural unit (a1-4) include structural units derived from monomers described in JP-A-2010-204646. Preferably, the structural units represented by the formulas (a1-4-1) to (a1-4-42) and the hydrogen atom corresponding to R a1 in the structural unit (a1-4) are replaced by a halogen atom, a haloalkyl group or an alkyl group. More preferably, the structural units represented by the formulas (a1-4-1) to (a1-4-5), formula (a1-4-10), formula (a1-4-13), formula (a1-4-14), formula (a1-4-19), and formula (a1-4-20) are included.

[0323]

Chemical formula

[0324] When the resin (A) contains the structural unit (a1-4), the content thereof is 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, still more preferably 25 mol% or more, even more preferably 30 mol% or more, still even more preferably 40 mol% or more, and still more preferably 50 mol% or more, based on the total of all the structural units of the resin (A). Further, it is 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, still more preferably 80 mol% or less, even more preferably 75 mol% or less, still even more preferably 70 mol% or less, and still more preferably 65 mol% or less. Specifically, it is preferably 10 to 95 mol%, more preferably 15 to 90 mol%, still more preferably 20 to 85 mol%, even more preferably 20 to 70 mol%, and still even more preferably 20 to 60 mol%.

[0325] Examples of the structural unit derived from the (meth)acrylic monomer having the group (2) include the structural unit represented by the formula (a1-5) (hereinafter sometimes referred to as "structural unit (a1-5)").

[0326] [Chemical formula]

[0327] [In the 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.

[0328] Z a1 represents a single bond or *-(CH 2 ) h3 -CO-L 54 -, h3 represents an integer of 1 to 4, and * represents the bonding site with L 51 . L 51 , L 52 , L 53 and L 54Each independently represents -O- or -S-.

[0329] s1 represents an integer of any one of 1 to 3. s1′ represents an integer of any one of 0 to 3. R a8 Examples of the halogen atom and the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in R include R of formula (a1-0), formula (a1-1) and formula (a1-2). a01 R a4 and R a5 are the same as those exemplified by.

[0330] In formula (a1-5), R a8 is preferably a hydrogen atom, a methyl group or a trifluoromethyl group. L 51 is preferably an oxygen atom.

[0331] L 52 and L 53 Among them, it is preferable that one is -O- and the other is -S-. s1 is preferably 1. s1′ is preferably an integer of any one of 0 to 2.

[0332] Z a1 is preferably a single bond or *-CH 2 -CO-O-. Examples of the structural unit (a1-5) include structural units derived from monomers described in JP-A-2010-61117. Among them, the structural units represented by formula (a1-5-1) to formula (a1-5-4) are preferable, and the structural unit represented by formula (a1-5-1) or formula (a1-5-2) is more preferable.

[0333]

Chemical formula

[0334] When the resin (A) contains the structural unit (a1-5), its content is 1 mol% or more, preferably 2 mol% or more, more preferably 3 mol% or more, still more preferably 5 mol% or more, even more preferably 10 mol% or more, still even more preferably 20 mol% or more, and even more preferably 25 mol% or more, based on all the structural units of the resin (A). Also, it is 80 mol% or less, preferably 70 mol% or less, more preferably 60 mol% or less, still more preferably 50 mol% or less, even more preferably 45 mol% or less, still even more preferably 40 mol% or less, and even more preferably 30 mol% or less. Specifically, 1 to 50 mol% is preferable, 3 to 45 mol% is more preferable, 5 to 40 mol% is still more preferable, and 5 to 30 mol% is even more preferable.

[0335] Examples of the structural unit having the group (1) in the structural unit (a1) include a structural unit represented by the formula (a1-6) (hereinafter sometimes referred to as "structural unit (a1-6)").

[0336]

Chemical formula

[0337] [In the 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.

[0338] R a62 、R a63 and R a64 each independently represent 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 atom to which they are bonded.

[0339] X a61 is a single bond, -CO-O-*, or -CO-NR a65represents -*, where * represents the bonding site with Ar, and R a65 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X a62 represents a single bond, *-O-L a61 - or *-CO-O-L a62 -, where * represents the bonding site with Ar, and L a61 and L a62 each independently represent an alkanediyl group having 1 to 4 carbon atoms.

[0340] Ar represents an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent. R a61 Examples of the halogen atom and the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in R are the same as those exemplified by R of formula (a1-0), formula (a1-1) and formula (a1-2). a01 R a4 and R a5 in formula (a1-2).

[0341] R a61 is preferably a hydrogen atom, a methyl group or a trifluoromethyl group. R a62 R a63 R a64 and R a65 Examples of the alkyl group in R include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group and the like. 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 still more preferably a methyl group or an ethyl group.

[0342] R a62 R a63 and R a64 Examples of the cyclic hydrocarbon group in R include an alicyclic hydrocarbon group and an aromatic hydrocarbon group. The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, etc. Examples of the polycyclic alicyclic hydrocarbon group include a decahydronaphthyl group, an adamantyl group, a norbornyl group, etc. The number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 16, more preferably 3 to 12.

[0343] Examples of the aromatic hydrocarbon group include a phenylene group, a naphthylene group, etc. 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, etc.

[0344] R a62 and R a63 Examples of the ring formed by bonding with each other include an adamantane ring, a cyclopentane ring, a cyclohexane ring, etc. Specifically, when R a62 and R a63 bond with each other to form a ring, examples of -C(R a62 )(R a63 )(R a64 ) include the following groups. * represents the bonding site with the oxygen atom. The number of carbon atoms of the ring is preferably 3 to 16, more preferably 3 to 12.

[0345]

Chemical formula

[0346] L a61 and L a62Examples of the C1-C4 alkanediyl group 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, a 2-methylpropane-1,2-diyl group, and the like.

[0347] L a61 and L a62 are each independently preferably a methylene group or an ethylene group. X a61 is preferably a single bond or -CO-O-*, and more preferably a single bond.

[0348] X a62 is preferably a single bond or *-O-L a61 -, and more preferably a single bond. Examples of the C6-C20 aromatic hydrocarbon group of Ar include a phenylene group, a naphthylene group, an anthrylene group, a biphenylene group, a phenanthrylene group, and the like.

[0349] Examples of the substituent that the aromatic hydrocarbon group may have include a halogen atom, a hydroxy group, a C1-C6 alkyl group, a C1-C6 alkoxy group, a C2-C12 alkoxyalkyl group, a C2-C12 alkoxyalkoxy group, a C2-C4 alkylcarbonyl group, a C2-C4 alkylcarbonyloxy group, an acryloyloxy group, a methacryloyloxy group, and the like.

[0350] Examples of the halogen atom include a fluorine atom, an iodine atom, a chlorine atom, a bromine atom, and the like. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group. The alkyl group is preferably a C1-C4 alkyl group, more preferably a methyl group or an ethyl group, and even more preferably a methyl group.

[0351] 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.

[0352] 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.

[0353] Examples of the alkoxyalkoxy group include a methoxymethoxy group, a methoxyethoxy group, an ethoxymethoxy group, an ethoxyethoxy group, a propoxymethoxy group, an isopropoxymethoxy group, a butoxymethoxy group, a sec-butoxymethoxy group, and a tert-butoxymethoxy group. The alkoxyalkoxy group is preferably an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a methoxyethoxy group or an ethoxyethoxy group.

[0354] 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.

[0355] 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.

[0356] Preferred substituents include 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 preferred are a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group, or an ethoxy-methoxy group. Even more preferred are a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, or an ethoxyethoxy group.

[0357] 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 Formula (a1-6-1) to Formula (a1-6-44). Preferred are structural units represented by Formula (a1-6-1) to Formula (a1-6-9). More preferred are structural units represented by Formula (a1-6-1), Formula (a1-6-2), Formula (a1-6-4), Formula (a1-6-5), Formula (a1-6-7), or Formula (a1-6-8). Even more preferred are structural units represented by Formula (a1-6-1) or Formula (a1-6-2).

[0358] [Chemical formula]

[0359] [Chemical formula]

[0360] In the above structural unit, a structural unit in which the hydrogen atom corresponding to R a61 is replaced with a methyl group or the like, and in the following structural unit, a structural unit in which the methyl group corresponding to R a61 is replaced with a hydrogen atom or the like are also included as the structural unit (a1-6).

[0361] When the resin (A) contains the structural unit (a1-6), its content is 3 mol% or more, preferably 5 mol% or more, more preferably 7 mol% or more, still more preferably 10 mol% or more, even more preferably 20 mol% or more, still even more preferably 30 mol% or more, and even more preferably 40 mol% or more, based on all the structural units of the resin (A). Also, it is 80 mol% or less, preferably 75 mol% or less, more preferably 70 mol% or less, still more preferably 65 mol% or less. Specifically, it is preferably 3 to 80 mol%, more preferably 5 to 75 mol%, still more preferably 7 to 70 mol%, still even more preferably 7 to 65 mol%, and particularly preferably 10 to 65 mol%.

[0362] In addition, examples of the structural unit (a1) also include the following structural units.

[0363] [Chemical formula]

[0364] When the resin (A) contains the structural units represented by the formulas (a1-7-1) to (a1-7-7), its content is 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, still more preferably 25 mol% or more, even more preferably 30 mol% or more, still even more preferably 40 mol% or more, and even more preferably 50 mol% or more, based on all the structural units of the resin (A). Also, it is 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, still more preferably 80 mol% or less, even more preferably 75 mol% or less, still even more preferably 70 mol% or less, and even more preferably 60 mol% or less. Specifically, it is preferably 10 to 95 mol%, more preferably 15 to 90 mol%, still more preferably 20 to 85 mol%, still even more preferably 20 to 70 mol%, and particularly preferably 20 to 60 mol%.

[0365] In addition, examples of the structural unit (a1) also include the following structural units.

[0366] [Chemical formula]

[0367] When the resin (A) contains a structural unit represented by the formulas (a1-8-1) to (a1-8-3), its content is 10 mol% or more, preferably 15 mol% or more, more preferably 20 mol% or more, still more preferably 25 mol% or more, even more preferably 30 mol% or more, still even more preferably 40 mol% or more, and even more preferably 50 mol% or more, based on all the structural units of the resin (A). Also, it is 95 mol% or less, preferably 90 mol% or less, more preferably 85 mol% or less, still more preferably 80 mol% or less, even more preferably 75 mol% or less, still even more preferably 70 mol% or less, and even more preferably 60 mol% or less. Specifically, 10 to 60 mol% is preferable, 15 to 55 mol% is more preferable, 20 to 50 mol% is still more preferable, 20 to 45 mol% is even more preferable, and 20 to 40 mol% is particularly preferable.

[0368] 〈Structural unit (s)〉 The structural unit (s) is derived from a monomer having no acid-labile group (hereinafter sometimes referred to as "monomer (s)"). As the monomer that leads to the structural unit (s), a monomer having no acid-labile group known in the resist field can be used.

[0369] As the structural unit(s), it is preferable to have a hydroxy group, a carboxy group or a lactone ring. By using a resin containing a structural unit having a hydroxy group or a carboxy group and not having an acid-labile group (hereinafter sometimes referred to as "structural unit (a2)") and / or a structural unit having a lactone ring and not having an acid-labile group (hereinafter sometimes referred to as "structural unit (a3)") in the resist composition of the present invention, the resolution of the resist pattern and the adhesion to the substrate can be improved. In addition to the above-described structural units, the structural unit(s) include a structural unit having a halogen atom (hereinafter sometimes referred to as "structural unit (a4)". However, the structural unit represented by formula (I) is excluded.), a structural unit having a non-leaving hydrocarbon group (hereinafter sometimes referred to as "structural unit (a5)"), a structural unit having a sultone structure (hereinafter sometimes referred to as "structural unit (a6)"), or a structural unit that decomposes upon exposure to generate an acid (hereinafter sometimes referred to as "structural unit (a7)").

[0370] 〈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.

[0371] [Chemical formula]

[0372] [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.

[0373] A a21 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and -CH 2 - in the alkanediyl group is -CH 2 - may be replaced by -O-, -CO- or -NR a28 -.

[0374] R a28represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. L a21 represents a single bond or a hydrocarbon group having 1 to 28 carbon atoms, and the hydrocarbon group may have a substituent, and -CH 2 - in the hydrocarbon group may be replaced by -O-, -CO-, -S- or -SO 2 -.

[0375] L a22 represents a single bond or a chain hydrocarbon group having 1 to 12 carbon atoms which may have a fluorine atom, and -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-.

[0376] na2 represents any integer from 1 to 5. When na2 is 2 or more, a plurality of Ls a22 may be the same as or different from each other. R a2 Examples of the halogen atom in R include a fluorine atom, an iodine atom, a chlorine atom, a bromine atom and the like.

[0377] R a2 Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in R 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, an iodomethyl group. The number of carbon atoms of the alkyl group is preferably 1 to 4, more preferably 1 to 3, and still more preferably 1 or 2.

[0378] R a2is 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 still more preferably a hydrogen atom or a methyl group. A a21 Examples of the alkanediyl group of a21 include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, etc., and branched alkanediyl groups such as butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group, heptane-1,6-diyl group, octane-1,7-diyl group, nonane-1,8-diyl group, decane-1,9-diyl group, undecane-1,10-diyl group, etc. The number of carbon atoms of the alkanediyl group is preferably 1 to 10, more preferably 1 to 8, still more preferably 1 to 6, even more preferably 1 to 4, still even more preferably 1 to 3, and still more preferably 1 or 2.

[0379] R a28 Examples of the alkyl group of a28 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, and tert-butyl group. A a21 When -CH a21 contained in the alkanediyl group of a21 is replaced by -O-, -CO- or -NR 2 , the number of carbon atoms before replacement is taken as the number of carbon atoms of the alkanediyl group. 2 - is replaced by -O-, -CO- or -NR a28 a28 - is replaced by -O-, -CO- or -NR a21 , the group formed after replacement is a hydroxy group (-CH 2 contained in the methyl group)

[0380] A a21 When -CH a21 contained in the alkanediyl group of a21 is replaced by -O-, -CO- or -NR 2 2 - is replaced by -O-, -CO- or -NR a28 a28 - is replaced by -O-, -CO- or -NR 2 , the group formed after replacement is a hydroxy group (-CH 2 contained in the methyl group) 2- is a group replaced by -O-), carboxy group (-CH contained in the ethyl group 2 -CH 2 - is a group replaced by -O-CO-), carbonyl group (-CH contained in the methylene group 2 - is a group replaced by -CO-), oxy group (-CH contained in the methylene group 2 - is a group replaced by -O-), amino group (-CH contained in the methyl group 2 - is a group replaced by -NR a28 -), alkoxy group (-CH at any position contained in the alkyl group 2 - is a group replaced by -O-), alkoxycarbonyl group (-CH at any position contained in the alkyl group 2 -CH 2 - is a group replaced by -O-CO-), alkylcarbonyl group (-CH at any position contained in the alkyl group 2 - is a group replaced by -CO-), alkylcarbonyloxy group (-CH at any position contained in the alkyl group 2 -CH 2 - is a group replaced by -CO-O-), alkylamino group (-CH at any position contained in the alkyl group 2 - is a group replaced by -NR a28 -), peptide group (-CH contained in the ethylene group 2 -CH 2 - is a group replaced by -CO-NR a28 -), alkanediyl-oxy group (-CH contained in the alkanediyl group 2 - is a group replaced by -O-), alkanediyl-oxycarbonyl group (-CH at any position contained in the alkanediyl group 2 -CH 2 - is a group replaced by -O-CO-), alkanediylcarbonyl group (-CH at any position contained in the alkanediyl group 2 - is a group replaced by -CO-), alkanediylcarbonyl-oxy group (-CH at any position contained in the alkanediyl group 2 -CH 2- is a group replaced by -CO-O-, an alkanediylamino group (in any position of the alkanediyl group, -CH 2 - is a group replaced by -NR a28 - etc. Examples of these replaced groups include those similar to the groups exemplified in this specification within the range allowed by the upper limit of the number of carbon atoms.

[0381] Among them, for the -CH a21 contained in the alkanediyl group of A 2 - being replaced by -O-, -CO- or -NR a28 -, the groups include *-O-, *-CO-O-, *-O-CO-, *-CO-O-A a22 -CO-O-, *-O-CO-A a22 -O-, *-O-A a22 -CO-O-, *-CO-O-A a22 -O-CO-, *-O-CO-A a22 -O-CO-, *-CO-NR a28 -. Among them, *-CO-O-, *-CO-O-A a22 -CO-O-, *-O-A a22 -CO-O-, *-CO-NR a28 - are preferred. Here, A a22 represents an alkanediyl group having 1 to 8 carbon atoms, and * represents the bonding site with the carbon atom to which R a2 is bonded. The alkanediyl group of A a22 includes the same alkanediyl group as A a21 within the range allowed by the upper limit of the number of carbon atoms.

[0382] A a21 is preferably a single bond, *-CO-O- or *-CO-O-A a22 -CO-O-, more preferably a single bond, *-CO-O- or *-CO-O-CH 2 -CO-O-, and even more preferably a single bond or *-CO-O-.

[0383] L a21The hydrocarbon group in it is a (na2 + 1)-valent hydrocarbon group, and examples thereof include linear or branched chain hydrocarbon groups, alicyclic hydrocarbon groups of monocyclic or polycyclic (including spiro rings, condensed rings, bridged rings, etc.), and cyclic hydrocarbon groups such as aromatic hydrocarbon groups. A group formed by 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) may also be used.

[0384] L a21 Examples of the chain hydrocarbon group of L include divalent to hexavalent chain hydrocarbon groups such as alkanediyl groups, alkanetriyl groups, alkanetetrayl groups, alkanepentayl groups, and alkanexayl groups.

[0385] Examples of the alkanediyl group include, for example, the same alkanediyl group as A a21 and the like. Examples of the alkanetriyl group include methanetriyl group, ethanetriyl group, propanetriyl group, butanetriyl group, pentanetriyl group, hexanetriyl group, heptanetriyl group, octanetriyl group, nonanetriyl group, decanetriyl group, undecanetriyl group, dodecanetriyl group, tridecanetriyl group, tetradecanetriyl group, pentadecanetriyl group, hexadecanetriyl group, and heptadecanetriyl group.

[0386] Examples of the alkanetetrayl group include methanetetrayl group, ethanetetrayl group, propanetetrayl group, butanetetrayl group, pentanetetrayl group, hexanetetrayl group, heptanetetrayl group, octanetetrayl group, nonanetetrayl group, decanetetrayl group, undecanetetrayl group, dodecanetetrayl group, tridecanetetrayl group, tetradecanetetrayl group, pentadecanetetrayl group, hexadecanetetrayl group, and heptadecanetetrayl group.

[0387] Examples of the alkanepentayl group include methanepentayl group, ethanepentayl group, propanepentayl group, butanepentayl group, pentanepentayl group, hexanepentayl group, and the like.

[0388] In addition, groups in which one or more of the hydrogen atoms of the above-described group are replaced with a bonding site can also be mentioned. L a21 The number of carbon atoms of the chain hydrocarbon group of is preferably from 1 to 18, more preferably from 1 to 12, still more preferably from 1 to 10, even more preferably from 1 to 9, still even more preferably from 1 to 8, still more preferably from 1 to 6, even more preferably from 1 to 5, and particularly preferably from 1 to 4.

[0389] L a21 Examples of the monocyclic and polycyclic alicyclic hydrocarbon groups in include the following alicyclic hydrocarbon groups and the like. The bonding site can be at any position.

[0390]

Chemical formula

[0391] For example, divalent to hexavalent alicyclic hydrocarbon groups such as a cycloalkanediyl group, a cycloalkanetriyl group, a cycloalkanetetrayl group, a cycloalkanepentayl group, and a cyclohexanehexayl group can be mentioned.

[0392] 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, cyclodecanetetrayl group, and Examples of the polycyclic alicyclic hydrocarbon group 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]octanediy group, norbornanetril group, adamantanetril group, decahydronaphthalenetril group, bicyclo[3.3.0]octanetril group, norbornanetetrayl group, adamantanetetrayl group, decahydronaphthalenetetrayl group, bicyclo[3.3.0]octanetetrayl group, and the like.

[0393] Examples also include a group in which one or more hydrogen atoms of the above-described group are replaced by a bonding site, and the like. The number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 20, more preferably 3 to 18, still more preferably 3 to 16, even more preferably 3 to 12, still even more preferably 6 to 12, and particularly preferably 6 to 10.

[0394] L a21 Examples of the aromatic hydrocarbon group in L include divalent to hexavalent aromatic hydrocarbon groups such as arylene group, arenetricyl group, arenetetrayl group, arenepentayl group, arenexayl group, and the like.

[0395] Specifically, examples include phenylene group, naphthylene group, anthrylene group, biphenylene group, phenanthrylene group, benzenetricyl group, naphthalenetricyl group, anthracenetricyl group, biphenyleneetricyl group, phenanthrenetricyl group, benzenetetrayl group, naphthalenetetrayl group, anthracenetetrayl group, biphenyleneetetrayl group, phenanthrenetetrayl group, and the like.

[0396] Examples also include a group in which one or more hydrogen atoms of the above-described group are replaced by a bonding site, and the like. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 20, more preferably 6 to 18, still more preferably 6 to 14, even more preferably 6 to 12, still even more preferably 6 to 10.

[0397] Examples of groups formed by combining two or more of them include a group formed by combining an alicyclic hydrocarbon group and a chain hydrocarbon group, a group formed by combining an aromatic hydrocarbon group and a chain hydrocarbon group, a group formed by combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group, a group formed by combining an alicyclic hydrocarbon group, a chain hydrocarbon group, and an aromatic hydrocarbon group, etc. In the combination, two or more alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may be combined respectively. Also, any group may be bonded to A a21 and L a22 as well.

[0398] Examples of the group in which -CH 2 - contained in the hydrocarbon group is replaced by -O-, -S-, -SO 2 -, or -CO- include a hydroxy group (a group in which -CH 2 - contained in the methyl group is replaced by -O-), a carboxy group (a group in which -CH 2 -CH 2 - contained in the ethyl group is replaced by -O-CO-), a thiol group (a group in which -CH 2 - contained in the methyl group is replaced by -S-), an alkoxy group (a group in which -CH 2 - at any position contained in the alkyl group is replaced by -O-), an alkylthio group (a group in which -CH 2 - at any position contained in the alkyl group is replaced by -S-), an alkoxycarbonyl group (a group in which -CH 2 -CH 2 - at any position contained in the alkyl group is replaced by -O-CO-), an alkylsulfonyl group (a group in which -CH 2 - at any position contained in the alkyl group is replaced by -SO 2 -), an alkylcarbonyl group (a group in which -CH 2 - at any position contained in the alkyl group is replaced by -CO-), an alkylcarbonyloxy group (a group in which -CH 2 -CH 2 - at any position contained in the alkyl group is replaced by -CO-O-), an oxy group (a group in which -CH 2- is a group replaced by -O-), a carbonyl group (-CH contained in a methylene group 2 - is a group replaced by -CO-), a thio group (-CH contained in a methylene group 2 - is a group replaced by -S-), a sulfonyl group (-CH contained in a methylene group 2 - is replaced by -SO 2 -), an alkanediyl-oxy group (-CH at any position contained in an alkanediyl group 2 - is a group replaced by -O-), an alkanediyl-oxy-carbonyl group (-CH at any position contained in an alkanediyl group 2 -CH 2 - is a group replaced by -O-CO-), an alkanediyl-carbonyl group (-CH at any position contained in an alkanediyl group 2 - is a group replaced by -CO-), an alkanediyl-carbonyl-oxy group (-CH at any position contained in an alkanediyl group 2 -CH 2 - is a group replaced by -CO-O-), an alkanediyl-sulfonyl group (-CH at any position contained in an alkanediyl group 2 - is replaced by -SO 2 -), an alkanediyl-thio group (-CH at any position contained in an alkanediyl group 2 - is a group replaced by -S-), a cycloalkoxy group, a cycloalkyl-alkoxy group, an alkoxy-carbonyl-oxy group, an aromatic hydrocarbon group-carbonyl-oxy group, an aromatic hydrocarbon group-carbonyl group, an aromatic hydrocarbon group-oxy group, a group formed by combining two or more of these groups, etc. may be mentioned. Further, a group in which one or more hydrogen atoms of these groups are replaced by a bonding site, etc. may also be mentioned.

[0399] Examples of the alkoxy group include alkoxy groups having 1 to 27 carbon atoms, such as methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, undecyloxy group and the like. The number of carbon atoms of the alkoxy group is preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0400] Examples of the alkylthio group include alkylthio groups having 1 to 27 carbon atoms, such as methylthio group, ethylthio group, propylthio group, butylthio group and the like. The number of carbon atoms of the alkylthio group is preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0401] Examples of the alkoxycarbonyl group include alkoxycarbonyl groups having 2 to 27 carbon atoms, such as methoxycarbonyl group, ethoxycarbonyl group, butoxycarbonyl group and the like. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 28 carbon atoms, such as acetyl group, propionyl group and butyryl group and the like. Examples of the alkylcarbonyloxy group include alkylcarbonyloxy groups having 2 to 27 carbon atoms, such as acetyloxy group, propionyloxy group, butyryloxy group and the like. The number of carbon atoms of the alkoxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms of the alkylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms of the alkylcarbonyloxy group is preferably 2 to 11, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3.

[0402] Examples of the alkylsulfonyl group include alkylsulfonyl groups having 1 to 27 carbon atoms, such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group and the like. The number of carbon atoms of the alkylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0403] Examples of the alkanedioxy group include alkanedioxy groups having 1 to 27 carbon atoms, such as methyleneoxy group, ethyleneoxy group, propanedioloxy group, butanedioloxy group, pentanedioloxy group and the like. The number of carbon atoms of the alkanedioxy group is preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0404] Examples of the alkanediyl-oxycarbonyl group include alkanediyl-oxycarbonyl groups having 2 to 27 carbon atoms, such as a methylene-oxycarbonyl group, an ethylene-oxycarbonyl group, a propanediyl-oxycarbonyl group, and a butanediyl-oxycarbonyl group. Examples of the alkanediyl-carbonyl group include alkanediyl-carbonyl groups having 2 to 28 carbon atoms, such as a methylene-carbonyl group, an ethylene-carbonyl group, a propanediyl-carbonyl group, a butanediyl-carbonyl group, and a pentanediyl-carbonyl group. Examples of the alkanediyl-carbonyloxy group include alkanediyl-carbonyloxy groups having 2 to 27 carbon atoms, such as a methylene-carbonyloxy group, an ethylene-carbonyloxy group, a propanediyl-carbonyloxy group, and a butanediyl-carbonyloxy group. The number of carbon atoms of the alkanediyl-oxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms of the alkanediyl-carbonyl group is preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms of the alkanediyl-carbonyloxy group is preferably 2 to 11, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3.

[0405] Examples of the alkanediyl-thio group include alkanediyl-thio groups having 1 to 27 carbon atoms, such as a methylene-thio group, an ethylene-thio group, and a propanediyl-thio group. The number of carbon atoms of the alkanediyl-thio group is preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0406] Examples of the alkanediylsulfonyl group include alkanediylsulfonyl groups having 1 to 27 carbon atoms, such as methylenesulfonyl group, ethylenesulfonyl group, propylenesulfonyl group and the like. The number of carbon atoms of the alkanediylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0407] Examples of the cycloalkoxy group include cycloalkoxy groups having 3 to 27 carbon atoms, such as cyclohexyloxy group and the like. Examples of the cycloalkylalkoxy group include cycloalkylalkoxy groups having 4 to 27 carbon atoms, such as cyclohexylmethoxy group and the like. Examples of the alkoxycarbonyloxy group include alkoxycarbonyloxy groups having 2 to 26 carbon atoms, such as butoxycarbonyloxy group and the like. Examples of the aromatic hydrocarbon group-carbonyl-oxy group include aromatic hydrocarbon group-carbonyl-oxy groups having 7 to 27 carbon atoms, such as benzoyloxy group and the like. Examples of the aromatic hydrocarbon group-carbonyl group include aromatic hydrocarbon group-carbonyl groups having 7 to 28 carbon atoms, such as benzoyl group and the like. Examples of the aromatic hydrocarbon group-oxy group include aromatic hydrocarbon group-oxy groups having 6 to 27 carbon atoms, such as phenyloxy group and the like.

[0408] In addition, -CH 2 - in the alicyclic hydrocarbon group replaced by -O-, -S-, -CO- or -SO 2 - includes the following groups and the like. Among the groups represented below, groups in which -O- is replaced by -S- and -CO- is replaced by -SO 2 - are also included. The bonding site can be at any position.

[0409]

Chemical formula

[0410] -CH contained in the combined group 2- is -O-, -S-, -CO- or -SO 2 Examples of the group replaced by - include the following groups and the like. The bonding site can be at any position.

[0411]

Chemical formula

[0412] L a21 The hydrocarbon group in may have one or more substituents. Examples of the substituent include a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, an alkyl group having 1 to 16 carbon atoms (wherein -CH 2 - in - may be replaced by -O- or -CO-), an acryloyloxy group, a methacryloyloxy group, and the like.

[0413] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like. L a21 By having a halogen atom as a substituent, the hydrocarbon group in can substantially have a substituent such as a haloalkyl group. Examples of the haloalkyl group include an alkyl fluoride group, an alkyl chloride group, an alkyl bromide group, an alkyl iodide group, etc., for example, chloromethyl group, bromomethyl group, iodomethyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluorobutyl group, etc. The number of carbon atoms of the haloalkyl group is preferably 1 to 8, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0414] L a21 The hydrocarbon group of, by including a branched structure, L a21can substantially have substituents 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, a dodecyl group, and the like. The number of carbon atoms of the alkyl group is preferably 1 to 12, more preferably 1 to 10, still more preferably 1 to 8, even more preferably 1 to 6, still even more preferably 1 to 4, and even more preferably 1 to 3.

[0415] L a21 in the hydrocarbon group of -CH 2 - is replaced by a group such as -O- or -CO-, and L a21 can substantially have substituents 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, a methacryloyloxy group, and the like. The number of carbon atoms of the alkoxy group is preferably 1 to 12, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3. The number of carbon atoms of the alkoxycarbonyl group, the alkylcarbonyl group, and the alkylcarbonyloxy group is preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 to 3. The number of carbon atoms of the alkoxyalkyl group and the alkoxyalkoxy group is preferably 2 to 12, more preferably 2 to 8, still more preferably 2 to 6, and even more preferably 2 to 4.

[0416] Examples of the above groups also include those similar to those exemplified in this specification. L a21 Substituents that the hydrocarbon group in may optionally have include a halogen atom, a haloalkyl group having 1 to 8 carbon atoms, or an alkyl group having 1 to 12 carbon atoms (the -CH contained in the alkyl group 2- may be replaced by -O- or -CO-. ) is preferred, a halogen atom, a haloalkyl group having 1 to 6 carbon atoms or an alkyl group having 1 to 10 carbon atoms (the -CH contained in the alkyl group 2 - may be replaced by -O- or -CO-. ) is more preferred, 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 is even more preferred, 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 is even more preferred, and a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, a hydroxy group, a methoxy group or an ethoxyethoxy group is even more preferred.

[0417] Also, when the alkane diyl group of L a21 is replaced by -O- or -CO- etc., for example, *-L a23 -X a21 -(L a23 represents an alkane diyl group having 1 to 8 carbon atoms, X a21 represents -O-, -O-CO-, -CO-O- or -O-CO-O-, and * represents the bonding site with A a21 . ) is also preferred.

[0418] L a21 is a single bond, a chain hydrocarbon group having 1 to 12 carbon atoms which may have a substituent (provided that the -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO-. ), a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent (provided that the -CH contained in the cyclic hydrocarbon group 2 - may be replaced by -O-, -S-, -CO- or -SO 2 -. ) or a group formed by combining a chain hydrocarbon group having 1 to 8 carbon atoms which may have a substituent and a cyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent (provided that the -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO-, and the -CH contained in the cyclic hydrocarbon group2 - may be replaced by -O-, -S-, -SO 2 - or -CO-. It is preferably a chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent (however, -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO-. A cyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (however, -CH contained in the cyclic hydrocarbon group 2 - may be replaced by -O-, -S-, -CO- or -SO 2 -. Or a group formed by combining a chain hydrocarbon group having 1 to 6 carbon atoms which may have a substituent and a cyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (however, -CH contained in the chain hydrocarbon group 2 - may be replaced by -O- or -CO-, and -CH contained in the cyclic hydrocarbon group 2 - may be replaced by -O-, -S-, -SO 2 - or -CO-. It is more preferably so.

[0419] L a22Examples of the chain hydrocarbon group having 1 to 12 carbon atoms include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, etc., and branched alkanediyl groups such as ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group, propane-2,2-diyl group, 1-methylpropane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, 1-dimethylpropane-1,3-diyl group, pentane-2,4-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group, etc. The number of carbon atoms in the chain hydrocarbon group is preferably 1 to 10, more preferably 1 to 8, still more preferably 1 to 6, and even more preferably 1 to 4.

[0420] L a22 The fluorine atom(s) that [it] has may be one or two or more. L a22 The -CH 2 - contained in the chain hydrocarbon group of [it] may be replaced by -O- or -CO- etc., and these replaced groups include the same ones as those exemplified by L a21 within the range where the upper limit of the number of carbon atoms permits.

[0421] na2 is preferably any integer from 1 to 4, and more preferably any integer from 1 to 3. L a21 Examples of the structural unit (a2) when [it] is a single bond or a chain hydrocarbon group include, for example, the following structural units. Among the following structural units, the structural units in which the methyl group corresponding to R a2 is replaced by a hydrogen atom etc. are also preferred structural units of the structural unit (a2) in the same way as the following structural units.

[0422] [Chemical formula]

[0423] When producing a resist pattern from the resist composition of the present invention, when using a high-energy ray such as a KrF excimer laser (248 nm), an electron beam, or EUV (extreme ultraviolet light) as the exposure light source, as the structural unit (a2), a structural unit (a2) having a phenolic hydroxy group is preferable, and it is more preferable to use the structural unit (a2-A) described later. Further, when using an ArF excimer laser (193 nm) or the like, as the structural unit (a2), a structural unit (a2) having an alcoholic hydroxy group is preferable, and it is more preferable to use the structural unit (a2-C) described later. The structural unit (a2) may contain one kind alone or two or more kinds.

[0424] In the structural unit (a2), when L a21 is a cyclic hydrocarbon group, examples of the structural unit having a phenolic hydroxy group or a carboxy group include the structural unit represented by the formula (a2-A) (hereinafter sometimes referred to as "structural unit (a2-A)").

[0425] [Chemical formula]

[0426] [In the 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.

[0427] R a27represents 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.

[0428] A a21 represents a single bond or an alkanediyl group having 1 to 12 carbon atoms, and -CH 2 - in the alkanediyl group may be replaced by -O-, -CO- or -NR a28 -.

[0429] 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 any integer from 1 to 5, and when nA2 is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other.

[0430] na21 represents any integer from 0 to 4, and when na21 is 2 or more, the plurality of R a27 may be the same as or different from each other. mc represents any integer from 0 to 2. R a2 and A a21 are each groups similar to those exemplified by formula (a2).

[0431] R a27 Examples of the halogen atom of R include a fluorine atom, a chlorine atom, an iodine atom, a bromine atom and the like. R a27Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom include trifluoromethyl group, difluoromethyl group, methyl group, perfluoroethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, ethyl group, perfluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, propyl group, perfluorobutyl group, 1,1,2,2,3,3,4,4-octafluorobutyl group, butyl group, perfluoropentyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, pentyl group, hexyl group, perfluorohexyl group, chloromethyl group, bromomethyl group, and 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, still more preferably a methyl group or an ethyl group, and even more preferably a methyl group.

[0432] R a27 Examples of the alkoxy group include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, sec-butoxy group, and 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 even more preferably a methoxy group.

[0433] R a27 Examples of the alkoxyalkyl group include methoxymethyl group, ethoxyethyl group, propoxymethyl group, isopropoxymethyl group, butoxymethyl group, sec-butoxymethyl group, and 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 still more preferably a methoxymethyl group.

[0434] R a27Examples of the alkoxyalkoxy group include a methoxymethoxy group, a methoxyethoxy group, an ethoxymethoxy group, an ethoxyethoxy group, a propoxymethoxy group, an isopropoxymethoxy group, a butoxymethoxy group, a sec-butoxymethoxy group, and a tert-butoxymethoxy group. The alkoxyalkoxy group is preferably an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a methoxyethoxy group or an ethoxyethoxy group.

[0435] R a27 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, more preferably an acetyl group.

[0436] 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, more preferably an acetyloxy group.

[0437] R a27 R is preferably a halogen atom, a hydroxy group, a carboxy group, an optionally halogenated 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, still more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, or an ethoxyethoxy group.

[0438] nA2 is preferably 1, 2, 3, or 4, more preferably 1, 2, or 3, still more preferably 1 or 2. na21 is preferably 0, 1, 2, or 3, more preferably 0, 1, or 2, still more preferably 0 or 1.

[0439] mc is preferably 0 or 1. -X a2 -OH, in the case of a benzene ring, Aa21 It may be bonded to the o-position, m-position or p-position with respect to the bonding position of a21 . When the bonding position of a21 is the 1-position, it may be bonded to any of the 2nd to 8th positions, and a21 . When the bonding position of a21 is the 2nd position, it may be bonded to any of the 1st, 3rd to 8th positions. Among them, when the bonding position of

[0440] The structural unit (a2-A) includes structural units derived from monomers described in JP-A No. 2010-204634 and JP-A No. 2012-12577. Examples of the structural unit (a2-A) include structural units represented by formulas (a2-2-1) to (a2-2-32), formulas (a2-3-1) to (a2-3-24), and structural units represented by formulas (a2-2-1) to (a2-2-32), formulas (a2-3-1) to (a2-3-24), in which the methyl group corresponding to R in the structural unit (a2-A) a2 is replaced by a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group.

[0441]

Chemical formula

[0442]

Chemical formula

[0443] When the structural unit (a2-A) is included in the resin (A), the content of the structural unit (a2-A) is preferably 5 mol% or more, more preferably 10 mol% or more, still more preferably 15 mol% or more, and even more preferably 20 mol% or more, based on all the structural units. Also, it is preferably 80 mol% or less, more preferably 70 mol% or less, still more preferably 65 mol% or less, even more preferably 60 mol% or less, still even more preferably 50 mol% or less, still 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%, still more preferably 15 to 65 mol%, and even more preferably 20 to 65 mol%.

[0444] The structural unit (a2-A) can be incorporated into the resin (A) by polymerizing a compound that induces the structural unit (a2-A) (for example, a compound (a2-A') in which the -CH 2 -C(-R a2 )- of the structural unit (a2-A) is in the state of CH 2 =C(-R a2 ) before cleavage). Further, for example, after polymerization using the structural unit (a1-4), it can be incorporated into the resin (A) by treatment with an acid such as p-toluenesulfonic acid. Also, after polymerization using acetoxystyrene or the like, the structural unit (a2-A) can be incorporated into the resin (A) by treatment with an alkali such as tetramethylammonium hydroxide.

[0445] In the structural unit (a2), when L a21 is a cyclic hydrocarbon group, examples of the structural unit having an alcoholic hydroxy group or a carboxy group include the structural unit represented by the formula (a2-B) (hereinafter sometimes referred to as "structural unit (a2-B)"), the structural unit represented by the formula (a2-C) (hereinafter sometimes referred to as "structural unit (a2-C)"), and the structural unit represented by the formula (a2-D) (hereinafter sometimes referred to as "structural unit (a2-D)").

[0446] [Chemical formula]

[0447] [In formula (a2 - B) and formula (a2 - C), R a2 represents the same meaning as in formula (a2). R a27 represents the same meaning as in formula (a2 - A).

[0448] L a25 represents -O- or *-O-(CH 2 ) k2 -CO - O-, and k2 represents an integer from 1 to 7. * represents the bonding site with -CO-. X a2 represents a single bond or -CO-.

[0449] R a25 and R a26 each independently represent a hydrogen atom, a methyl group, or a hydroxy group. nB2 represents an integer from 1 to 5. When nB2 is 2 or more, the plurality of X a2 may be the same as or different from each other.

[0450] nB22 represents an integer from 0 to 8. When nB22 is 2 or more, the plurality of R a27 may be the same as or different from each other. nC22 represents an integer from 0 to 10. When nC22 is 2 or more, the plurality of R a27 may be the same as or different from each other.] L a25 is preferably -O-, -O-(CH 2 ) f1 -CO - O- (where f1 represents an integer from 1 to 4), and more preferably -O-.

[0451] R a2 is preferably a methyl group. X a2is preferably a single bond. R a25 is preferably a hydrogen atom.

[0452] 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.

[0453] nB2 is preferably 1, 2, 3 or 4, more preferably 1, 2 or 3, and even more preferably 1 or 2. nB22 is preferably any integer from 0 to 3, more preferably 0, 1 or 2, and even more preferably 0 or 1.

[0454] nC22 is preferably any integer from 0 to 6, more preferably any integer from 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 the monomers described in JP-A-2010-204646, the following structural units, and structural units in which the methyl group or hydrogen atom corresponding to R a2 in the following structural units is replaced with a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group. Among them, structural units represented by any of formula (a2-B-1) to formula (a2-B-5) and formula (a2-C-1) to formula (a2-C-9) are preferable.

[0455]

Chemical formula

[0456] When the resin (A) contains the structural unit (a2-B) or the structural unit (a2-C), the content thereof is 1 mol% or more, preferably 2 mol% or more, based on all the structural units of the resin (A). Further, it is 45 mol% or less, preferably 40 mol% or less, more preferably 35 mol% or less, still more preferably 20 mol% or less, and even more preferably 10 mol% or less. Specifically, it is 1 to 45 mol%, preferably 1 to 40 mol%, more preferably 1 to 35 mol%, still more preferably 1 to 20 mol%, and even more preferably 1 to 10 mol%.

[0457]

Chemical formula

[0458] [In formula (a2-D), R a2 and A a21 each represent the same meaning as in formula (a2). R a27 represents the same meaning as in formula (a2-A).

[0459] R a21 and R a22 each independently represent an alkyl fluoride 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.

[0460] nD2 represents any integer from 1 to 5. When nD2 is 2 or more, the groups in a plurality of parentheses may be the same as or different from each other. nD22 represents any integer from 0 to 4. When nD22 is 2 or more, a plurality of R a27 may be the same as or different from each other.

[0461] However, 1 ≤ nD2 + nD22 ≤ 5.] R a21 and R a22Examples of the alkyl fluoride group include, independently of each other, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a 3,3,3-trifluoropropyl group, a 4,4,4-trifluorobutyl group, and the like.

[0462] R a21 and R a22 Preferably, the group is a trifluoromethyl group. L a24 Examples of the alkanediyl group of L include a methylene group, an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-2,2-diyl group, and the like.

[0463] L a24 Preferably, L is a single bond or a methylene group. R a27 R 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, still more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, or an ethoxyethoxy group.

[0464] nD2 is preferably 1, 2, 3, or 4, more preferably 1, 2, or 3, still 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.

[0465] nD22 is preferably any integer from 0 to 3, more preferably any integer from 0 to 2, still more preferably 0 or 1, and even more preferably 0. As the structural unit (a2-D), a structural unit represented by the following formula (a2-D1) (hereinafter, may be referred to as "structural unit (a2-D1)") is more preferable.

[0466]

Chemical formula

[0467] [In formula (a2-D1), R a2 , A a21 , R a27 , nD2 and nD22 represent the same meaning as in formula (a2-D).] In formula (a2-D1), R a2 is preferably a hydrogen atom or a methyl group.

[0468] A a21 is preferably a single bond. Examples of the structural unit (a2-D) include the structural units described below.

[0469]

Chemical formula

[0470] In the structural units represented by formula (a2-D-1) to formula (a2-D-8), structural units in which the hydrogen atom corresponding to R a2 is replaced by a methyl group or the like, and in the structural units represented by formula (a2-D-9) to formula (a2-D-16), structural units in which the methyl group corresponding to R a2 is replaced by a hydrogen atom or the like can also be cited as specific examples of the structural unit (a2-D). Among them, the structural units represented by formula (a2-D-1) to formula (a2-D-8) are preferred, the structural units represented by formula (a2-D-1) to formula (a2-D-4) are more preferred, and the structural unit represented by formula (a2-D-1) is even more preferred.

[0471] When the resin (A) contains the structural unit (a2-D), its content is preferably 3 mol% or more, more preferably 5 mol% or more, still more preferably 10 mol% or more, based on all the structural units of the resin (A). Also, it is preferably 80 mol% or less, more preferably 75 mol% or less, still 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%, still more preferably 10 to 70 mol%, and even more preferably 10 to 65 mol%.

[0472] 〈Structural unit (a3)〉 The lactone ring possessed by 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 and another ring. Preferably, a γ-butyrolactone ring, an adamantane lactone ring, or a bridged ring containing a γ-butyrolactone ring structure (for example, the structural unit represented by the following formula (a3-2)) can be mentioned.

[0473] The structural unit (a3) is preferably a structural unit represented by the formula (a3-1), formula (a3-2), formula (a3-3), or formula (a3-4). These may be contained alone or in combination of two or more.

[0474] [Chemical formula]

[0475] [In the 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-(CH 2 ) k3 -CO-O-(k3 represents an integer from 1 to 7).

[0476] L a7 is -O-, *-O-L a8-O-, *-O-L a8 -CO-O-, *-O-L a8 -CO-O-L a9 -CO-O- or *-O-L a8 -O-CO-L a9 represents -O-.

[0477] L a8 and L a9 each independently represents an alkanediyl group having 1 to 6 carbon atoms. * represents 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.

[0478] X a3 represents -CH 2 - or an oxygen atom. R a21 represents an aliphatic hydrocarbon group having 1 to 4 carbon atoms. R a22 R a23 and R a25 each independently represents a carboxy group, a cyano group, or an aliphatic hydrocarbon group having 1 to 4 carbon atoms.

[0479] p1 represents any integer from 0 to 5. When p1 is 2 or more, the plurality of R a21 may be the same as or different from each other. q1 represents any integer from 0 to 3. When q1 is 2 or more, the plurality of R a22 may be the same as or different from each other.

[0480] r1 represents any integer from 0 to 3. When r1 is 2 or more, the plurality of R a23 may be the same as or different from each other. w1 represents any integer from 0 to 8. When w1 is 2 or more, the plurality of 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 R

[0481] R a18 、R a19 、R a20 and R a24 Examples of the halogen atom and the alkyl group which may have a halogen atom in R a01 、R a4 and R a5 include the same ones as those exemplified by R

[0482] L a8 and L a9 Examples of the alkanediyl group in L

[0483] In formulas (a3-1) to (a3-3), L a4 ~L a6 are each independently preferably -O- or, *-O-(CH 2 ) k3 -CO-O- in which k3 is an integer of 1 to 4, more preferably -O- and, *-O-CH 2 -CO-O-, still more preferably an oxygen atom.

[0484] L a7 is preferably -O- or *-O-L a8 -CO-O-, more preferably -O-, -O-CH 2 -CO-O- or -O-C2 H 4 is -CO-O-. R a18 , R a19 , R a20 and R a24 are 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 still more preferably a hydrogen atom or a methyl group.

[0485] R a21 is preferably a methyl group. R a22 , R a23 and R a25 are each independently preferably a carboxy group, a cyano group or a methyl group.

[0486] p1, q1 and r1 are each independently preferably any integer from 0 to 2, more preferably 0 or 1. w1 is preferably any integer from 0 to 2, more preferably 0 or 1.

[0487] In particular, formula (a3 - 4) is preferably formula (a3 - 4)'.

[0488] [Chemical formula]

[0489] (In the formula, R a24 , L a7 represents the same meaning as above.) Examples of the structural unit (a3) include structural units derived from the monomers described in JP - A - 2010 - 204646, the monomers described in JP - A - 2000 - 122294, and the monomers described in JP - A - 2012 - 41274. Examples of the structural unit (a3) include structural units represented by any of formula (a3 - 1 - 1), formula (a3 - 1 - 2), formula (a3 - 2 - 1), formula (a3 - 2 - 2), formula (a3 - 3 - 1), formula (a3 - 3 - 2), and formula (a3 - 4 - 1) to formula (a3 - 4 - 12), and in the above structural units, R in formula (a3 - 1) to formula (a3 - 4)a18 、 R a19 、 R a20 and R a24 A structural unit in which the methyl group corresponding to R is replaced by a hydrogen atom is preferred.

[0490]

Chemical formula

[0491] When the resin (A) contains the structural unit (a3), the total content thereof is 1 mol% or more, preferably 3 mol% or more, more preferably 5 mol% or more, still more preferably 10 mol% or more, based on all the structural units of the resin (A). Also, 70 mol% or less, preferably 65 mol% or less, more preferably 60 mol% or less, still more preferably 50 mol% or less, even more preferably 40 mol% or less, still even more preferably 30 mol% or less, still more preferably 25 mol% or less, and still even more preferably 20 mol% or less. Specifically, 1 to 70 mol%, preferably 3 to 70 mol%, more preferably 3 to 65 mol%, still more preferably 5 to 65 mol%, even more preferably 5 to 60 mol%, and still even more preferably 10 to 60 mol%.

[0492] In addition, the content ratio 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, still more preferably 5 mol% or more, and even more preferably 10 mol% or more, respectively, based on all the structural units of the resin (A). Further, it is preferably 60 mol% or less, more preferably 55 mol% or less, still more preferably 50 mol% or less, even more preferably 40 mol% or less, still even more preferably 30 mol% or less, even more preferably 25 mol% or less, and even more preferably 20 mol% or less. Specifically, 1 to 60 mol% is preferable, 3 to 60 mol% is more preferable, 3 to 55 mol% is still more preferable, 5 to 55 mol% is even more preferable, 5 to 50 mol% is even more preferable, and 10 to 50 mol% is still even more preferable.

[0493] <Structural unit (a4)> The structural unit represented by the formula (a4) is shown below.

[0494] [Chemical formula]

[0495] [In the formula (a4), R 41 represents a hydrogen atom or a methyl group. R 42 represents a saturated hydrocarbon group having a halogen atom with 1 to 24 carbon atoms, and -CH 2 - in the saturated hydrocarbon group may be replaced by -O- or -CO-.] R 42 The saturated hydrocarbon group represented thereby includes a linear or branched chain saturated hydrocarbon group, a monocyclic or polycyclic alicyclic saturated hydrocarbon group, and a group formed by combining these.

[0496] Examples of the chain saturated hydrocarbon group include linear alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, pentadecyl group, hexadecyl group, heptadecyl group and octadecyl group, and branched alkyl groups such as isopropyl group and isobutyl group.

[0497] Examples of the monocyclic or polycyclic alicyclic saturated hydrocarbon group include monocyclic alicyclic saturated hydrocarbon groups which are monocyclic cycloalkyl groups such as cyclopentyl group, cyclohexyl group, cycloheptyl group and cyclooctyl group; and polycyclic alicyclic saturated hydrocarbon groups which are polycyclic cycloalkyl groups such as decahydronaphthyl group, adamantyl group, norbornyl group and the following group (* represents the bonding site).

[0498]

Chemical formula

[0499] Examples of the group formed by 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, -alkanediyl group-alicyclic saturated hydrocarbon group-alkyl group and the like.

[0500] Examples of the alkanediyl group include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group and hexane-1,6-diyl group; and branched alkanediyl groups such as propane-1,2-diyl group, butane-1,3-diyl group, 2-methylpropane-1,2-diyl group, 1-methylbutane-1,4-diyl group and 2-methylbutane-1,4-diyl group. The terminal of the branched alkanediyl group may be a methyl group.

[0501] R 42Examples of the halogen atom included in the saturated hydrocarbon group include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom. R 42 The -CH 2 - in the saturated hydrocarbon group included in where - is replaced by -O- or -CO- includes a hydroxy group (the -CH 2 - in the methyl group where - is replaced by -O-), a carboxy group (the -CH 2 -CH 2 - in the ethyl group where - is replaced by -O-CO-), a carbonyl group (the -CH 2 - in the methylene group where - is replaced by -CO-), an oxy group (the -CH 2 - in the methylene group where - is replaced by -O-), an alkoxy group (any -CH 2 - in the alkyl group where - is replaced by -O-), an alkoxycarbonyl group (any -CH 2 -CH 2 - in the alkyl group where - is replaced by -O-CO-), an alkylcarbonyl group (any -CH 2 - in the alkyl group where - is replaced by -CO-), an alkylcarbonyloxy group (any -CH 2 -CH 2 - in the alkyl group where - is replaced by -CO-O-), an alkanedioxy group (any -CH 2 - in the alkanediyl group where - is replaced by -O-), an alkanedioxycarbonyl group (any -CH 2 -CH 2 - in the alkanediyl group where - is replaced by -O-CO-), an alkanediylcarbonyl group (any -CH 2 - in the alkanediyl group where - is replaced by -CO-), an alkanediylcarbonyloxy group (any -CH 2 -CH 2- is a group replaced by -CO-O-, a cycloalkoxy group, a cycloalkylalkoxy group, a group formed by combining two or more of these groups, and the like. These replaced groups include the same groups as those exemplified in the present specification within the range allowed by the upper limit of the number of carbon atoms.

[0502] As the structural unit (a4), R 42 is preferably a saturated hydrocarbon group having a fluorine atom, and R 42 Examples of the structural unit (a4) in which is a saturated hydrocarbon group having a fluorine atom include a structural unit represented by the formula (a4-1) (hereinafter sometimes referred to as "structural unit (a4-1)"), a structural unit represented by the formula (a4-2) (hereinafter sometimes referred to as "structural unit (a4-2)"), a structural unit represented by the formula (a4-3) (hereinafter sometimes referred to as "structural unit (a4-3)"), and a structural unit represented by the formula (a4-A) (hereinafter sometimes referred to as "structural unit (a4-A)").

[0503] The structural unit represented by the formula (a4-1) is the structural unit shown below.

[0504] [Chemical formula]

[0505] [In the 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.

[0506] L 42f represents an alkanediyl group having 1 to 8 carbon atoms having a fluorine atom or a cycloalkanediyl group having 3 to 12 carbon atoms having a fluorine atom. R 42f represents a hydrogen atom or a fluorine atom.] L 41Examples of the alkanediyl group in [the compound] include linear alkanediyl groups such as a methylene group, an ethylene group, a propane-1,3-diyl group, and a butane-1,4-diyl group; and branched alkanediyl groups such as an ethane-1,1-diyl group, a propane-1,2-diyl group, a butane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, and a 2-methylpropane-1,2-diyl group. The terminal of the branched alkanediyl group may be a methyl group.

[0507] L 42f Examples of the alkanediyl group having a fluorine atom in [the compound] include linear alkanediyl groups 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; and branched alkanediyl groups having a fluorine atom such as an ethane-1,1-diyl group having a fluorine atom, a propane-1,1-diyl group having a fluorine atom, a propane-1,2-diyl group having a fluorine atom, a propane-2,2-diyl group having a fluorine atom, a pentane-2,4-diyl group having a fluorine atom, a 2-methylpropane-1,3-diyl group having a fluorine atom, a 2-methylpropane-1,2-diyl group having a fluorine atom, a pentane-1,4-diyl group having a fluorine atom, and a 2-methylbutane-1,4-diyl group having a fluorine atom. The terminal of the branched alkanediyl group may be a methyl group which may have a fluorine atom.

[0508] L 42fExamples of the cycloalkanediyl group having a fluorine atom in [X] 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; and polycyclic cycloalkanediyl groups having a fluorine atom such as 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.

[0509] L 42f In [X], the number of fluorine atoms in the alkanediyl group and the cycloalkanediyl group having a fluorine atom may be 1 or more, and is preferably 2 or more. L 42f In [X], the alkanediyl group and the cycloalkanediyl group having a fluorine atom are preferably a perfluoroalkanediyl group and a perfluorocycloalkanediyl group, respectively.

[0510] L 42fExamples of the perfluoroalkanediyl group in [compound name] include difluoromethylene group, perfluoroethylene group, perfluoroethylfluoromethylene group, perfluoropropane-1,3-diyl group, perfluoropropane-1,2-diyl group, perfluoropropane-2,2-diyl group, perfluorobutane-1,4-diyl group, perfluorobutane-2,2-diyl group, perfluorobutane-1,2-diyl group, perfluoropentane-1,5-diyl group, perfluoropentane-2,2-diyl group, 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, perfluorooctane-4,4-diyl group, and the like.

[0511] L 42f Examples of the perfluorocycloalkanediyl group in [compound name] include perfluorocyclohexanediyl group, perfluorocyclopentanediyl group, perfluorocycloheptanediyl group, perfluoroadamantanediyl group, and the like.

[0512] 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 still more preferably a single bond or a methylene group.

[0513] 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 still more preferably a perfluoroalkanediyl group having 1 to 3 carbon atoms.

[0514] As the structural unit (a4-1), there are the following structural units and the structural unit (a4-1) in the following structural units where the methyl group corresponding to R 41 is replaced by a hydrogen atom.

[0515]

Chemical formula

[0516] The structural unit represented by the formula (a4-2) is the following structural unit.

[0517]

Chemical formula

[0518] [In the 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 have a fluorine atom, and -CH 2 - contained in the saturated hydrocarbon group may be replaced by -O- or -CO-.

[0519] R 43f represents a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a fluorine atom, and -CH 2 - contained in the saturated hydrocarbon group may be replaced by -O- or -CO-. However, at least one of L 43f and R 43f has a fluorine atom, and the upper limit of the total carbon number of L 43f and R 43f is 21.] L 43f and R 43f Examples of the saturated hydrocarbon group in include linear or branched chain saturated hydrocarbon groups, monocyclic or polycyclic alicyclic saturated hydrocarbon groups, and groups formed by combining these. Examples of the saturated hydrocarbon group in L 43f and R 43f are as follows for the saturated hydrocarbon group in L 43fand R 43f As long as the upper limit of the total number of carbon atoms of 43f allows, R in formula (a4) 42 includes the same groups as the saturated hydrocarbon groups exemplified as the saturated hydrocarbon groups of 42 .

[0520] L 43f As the saturated hydrocarbon group of 43f , an alkanediyl group having 1 to 6 carbon atoms or a group represented by formula (L43f-1) is preferable.

[0521] [Chemical formula]

[0522] [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 have a fluorine atom.

[0523] L 47f represents a single bond or a divalent saturated hydrocarbon group having 1 to 5 carbon atoms which may have a fluorine atom. X 46f and X 47f each independently represents -O-, -CO-, -CO-O- or -O-CO-.

[0524] However, the total number of carbon atoms of L 45f , L 46f , L 47f , X 46f and X 47f is 7 or less. * and ** are bonding sites, and ** is the bonding site with -O-CO-R 43f . In the group represented by formula (L43f-1), L 45f , L 46f and L 47fExamples 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 and a divalent alicyclic saturated hydrocarbon group. Specifically, 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, a 2-methylpropane-1,2-diyl group, and the like.

[0525] s is preferably 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 ** is the bonding site with -O-CO-R 43f and.

[0526]

Chemical formula

[0527] R 43f is preferably a saturated hydrocarbon group having a fluorine atom. Examples of the structural unit represented by formula (a4-2) in this case include structural units represented by formula (a4-2A) or (formula a4-2B).

[0528]

Chemical formula

[0529] [In formula (a4-2A) and formula (a4-2B), R 41 and L 43f represent the same as those in formula (a4-2). R 43fA represents a saturated hydrocarbon group having 1 to 20 carbon atoms and having a fluorine atom.

[0530] A 43frepresents a divalent saturated hydrocarbon group having 1 to 17 carbon atoms which may have a fluorine atom, and -CH 2 - may be replaced by -O- or -CO-.

[0531] X 43 represents -O-CO- or -CO-O-, and represents the bonding site with A 43f . R 43fB represents a saturated hydrocarbon group having 1 to 17 carbon atoms which may have a fluorine atom.

[0532] However, in formula (a4-2A), the total number of carbon atoms of L 43f and R 43fA is 21 or less, and in formula (a4-2B), the total number of carbon atoms of L 43f , A 43f , X 43 and R 43fB is 21 or less, and at least one of A 43f and R 43fB has at least one fluorine atom.] R 43fA 's saturated hydrocarbon group includes, as long as the upper limit of the number of carbon atoms permits, the same saturated hydrocarbon groups as those exemplified by R 42 .

[0533] R 43fA is preferably an alkyl group having 1 to 13 carbon atoms with a fluorine atom, a cycloalkyl group having 3 to 12 carbon atoms with a fluorine atom, or a group combining them, *-(CF 2 ) n43f -R 42′ (* represents the bonding site with the carbonyl group. n43f represents any integer from 1 to 6. R 42′ represents a hydrogen atom or a fluorine atom.) or a perfluorocycloalkyl group having 3 to 12 carbon atoms is more preferable.

[0534] A 43f and R 43fB 's saturated hydrocarbon groups include, as long as the upper limit of the number of carbon atoms permits, R 42Examples of the saturated hydrocarbon group similar to the saturated hydrocarbon group exemplified herein include those. A 43f is preferably a divalent chain saturated hydrocarbon group, a divalent alicyclic saturated hydrocarbon group which may have a fluorine atom, or a group combining them, more preferably a divalent chain saturated hydrocarbon group having a fluorine atom, and even more preferably a fluoroalkanediyl group having 1 to 6 carbon atoms.

[0535] R 43fB The saturated hydrocarbon group which may have a fluorine atom of R is preferably a chain saturated hydrocarbon group, an alicyclic saturated hydrocarbon group which may have a fluorine atom, or a group combining them, more preferably an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms which may have a fluorine atom, or a group combining them, and even more preferably a trifluoromethyl group, a difluoromethyl group, a methyl group, a perfluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,2,2-tetrafluoroethyl group, an ethyl group, a perfluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a propyl group, a perfluorobutyl group, a 1,1,2,2,3,3,4,4-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 heptyl group, a perfluoroheptyl group, an octyl group, a perfluorooctyl group and other fluoroalkyl groups, a cyclopropylmethyl group, a cyclopropyl group, a cyclobutylmethyl group, a cyclopentyl group, a cyclohexyl group, a perfluorocyclohexyl group, an adamantyl group, an adamantylmethyl group, an adamantyldimethyl group, a norbornyl group, a norbornylmethyl group, a perfluoroadamantyl group, a perfluoroadamantylmethyl group and the like.

[0536] In formula (a4-2B), *-A 43f -X 43 -R 43fB An example of the structure which the group represented by can take is the following structure (* is the bonding site with the carbonyl group).

[0537] [Chemical formula]

[0538] Examples of the structural unit represented by formula (a4-2A) include the structural units shown below and the structural units in the following structural units where the methyl group corresponding to R in the structural unit represented by formula (a4-2A) is replaced by a hydrogen atom. 41 The methyl group corresponding to R in the structural unit represented by formula (a4-2A) is replaced by a hydrogen atom.

[0539] [Chemical formula]

[0540] Examples of the structural unit represented by formula (a4-2B) include the structural units shown below and the structural units in the following structural units where the methyl group corresponding to R in the structural unit represented by formula (a4-2B) is replaced by a hydrogen atom. 41 The methyl group corresponding to R in the structural unit represented by formula (a4-2B) is replaced by a hydrogen atom.

[0541] [Chemical formula]

[0542] Examples of the structural unit (a4) also include the structural unit represented by formula (a4-3).

[0543] [Chemical formula]

[0544] [In formula (a4-3), R 41 represents a hydrogen atom or a methyl group. L 44f represents a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a fluorine atom, and -CH 2 - contained in the saturated hydrocarbon group may be replaced by -O- or -CO-.

[0545] R 44frepresents a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a fluorine atom, and -CH contained in the saturated hydrocarbon group 2 - may be replaced by -O- or -CO-. However, L 44f and R 44f at least one of them has a fluorine atom, and the upper limit of the total carbon number of L 44f and R 44f is 21.] Examples of the saturated hydrocarbon group in L 44f and R 44f include linear or branched chain saturated hydrocarbon groups, monocyclic or polycyclic alicyclic saturated hydrocarbon groups, and groups formed by combining these. Examples of the saturated hydrocarbon group in L 44f and R 44f include, as long as the upper limit of the total carbon number of L 44f and R 44f allows, groups similar to the saturated hydrocarbon groups exemplified as the saturated hydrocarbon group of R 42 in formula (a4).

[0546] L 44f is preferably an alkanediyl group having 1 to 14 carbon atoms (where -CH contained in the alkanediyl group 2 - may be replaced by -O- or -CO-.), and more preferably a group represented by -(CH 2 ) j1 -, -(CH 2 ) j2 -O-(CH 2 ) j3 - or -(CH 2 ) j4 -CO-O-(CH 2 ) j5 - (where j1 to j5 each independently represent an integer from 1 to 6). Also preferably, it is an alkanediyl group having 1 to 4 carbon atoms (where one -CH 2 - contained in the alkanediyl group may be replaced by -O-, and one -CH 2 -CH 2 - contained in the alkanediyl group may be replaced by -CO-O- or -O-CO-.).

[0547] R 44f is preferably a saturated hydrocarbon group having 1 to 10 carbon atoms and having a fluorine atom, more preferably an alkyl group having 1 to 10 carbon atoms and having a fluorine atom, an alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms and having a fluorine atom, or a group combining them, still more preferably an alkyl group having 1 to 10 carbon atoms and having a fluorine atom, and even more preferably an alkyl group having 1 to 6 carbon atoms and having a fluorine atom.

[0548] Examples of the structural unit represented by the formula (a4-3) include structural units represented by the following structural units and the following formulas, in which the methyl group corresponding to R in the structural unit (a4-3) is replaced by a hydrogen atom. 41 include structural units in which the methyl group corresponding to R is replaced by a hydrogen atom.

[0549]

Chemical formula

[0550] Examples of the structural unit (a4) also include a structural unit represented by the formula (a4-A).

[0551]

Chemical formula

[0552] [In the formula (a4-A), R 1 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom.

[0553] X 11 represents a single bond or *-CO-O-. * represents the bonding site with the carbon atom to which R 1 is bonded. L 1 represents an aliphatic hydrocarbon group having 1 to 28 carbon atoms which may have a substituent, and -CH 2 - contained in the aliphatic hydrocarbon group may be replaced by -O-, -S-, -SO 2 - or -CO-.

[0554] R 2 represents an alkyl fluoride group having 1 to 8 carbon atoms. R 3 represents a hydrogen atom or an alkyl fluoride group having 1 to 6 carbon atoms, and the alkyl fluoride group may be bonded to L 1 to form an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and -CH 2 - contained in the alicyclic hydrocarbon group may be replaced by -O-.

[0555] mi represents any integer from 1 to 4. When mi is 2 or more, the groups in the plurality of parentheses may be the same as or different from each other. R 1 Examples of the halogen atom and the alkyl group which may have a halogen atom in R include R of formula (a1-0), formula (a1-1) and formula (a1-2) a01 R a4 R a5 and those similar to those exemplified by R

[0556] R 1 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, still more preferably a hydrogen atom, a methyl group or an ethyl group, and still more preferably a hydrogen atom or a methyl group.

[0557] L 1 Examples of the aliphatic hydrocarbon group in L include a chain hydrocarbon group, a monocyclic or polycyclic (including a spiro ring, a condensed ring, a bridged ring, etc.) alicyclic hydrocarbon group, and a group formed by combining two or more of these groups (for example, a hydrocarbon group formed from an alicyclic hydrocarbon group and a chain hydrocarbon group) may also be used.

[0558] Examples of the chain hydrocarbon group include divalent to pentavalent chain hydrocarbon groups such as an alkanediyl group, an alkanetriyl group, an alkanetetrayl group, and an alkanepentayl group. Examples of the alkanediyl group include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, tridecane-1,13-diyl group, tetradecane-1,14-diyl group, pentadecane-1,15-diyl group, hexadecane-1,16-diyl group, and heptadecane-1,17-diyl group, and branched alkanediyl groups such as ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group, propane-2,2-diyl group, pentane-2,4-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group.

[0559] Examples also include groups in which one or more hydrogen atoms of the above-described groups are replaced by a bonding site. The number of carbon atoms in the chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 12, still more preferably 1 to 10, even more preferably 1 to 9, still even more preferably 1 to 8, still more preferably 1 to 6, still even more preferably 1 to 5, and particularly preferably 1 to 4.

[0560] Examples of the monocyclic or polycyclic alicyclic hydrocarbon group include the following alicyclic hydrocarbon groups. The bonding site can be at any position.

[0561]

Chemical formula

[0562] Examples include divalent to pentavalent alicyclic hydrocarbon groups such as cycloalkanediyl group, cycloalkanetriyl group, cycloalkanetetrayl group, and cycloalkanepentayl group. Specifically, monocyclic alicyclic hydrocarbon groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclooctane-1,5-diyl group, and polycyclic alicyclic hydrocarbon groups such as spiro rings having a cycloalkanediyl group, norbornanediyl group or adamantanediyl group each having a cycloalkanediyl group, 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]octanediy group, spirocyclohexane-1,2′-cyclopentane-diyl group, spiroadamantane-2,3′-cyclopentane-diyl group, etc., which are spiro-bonded to each other.

[0563] In addition, groups in which one or more hydrogen atoms of the above-mentioned groups are replaced at the bonding site, etc. are also included. The number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 20, more preferably 3 to 18, still more preferably 3 to 16, and even more preferably 3 to 12.

[0564] Examples of the group combined with two or more types include a group combining an alicyclic hydrocarbon group and a chain hydrocarbon group. In the combination, two or more types of alicyclic hydrocarbon groups and chain hydrocarbon groups may be combined respectively. Also, any group may be bonded to X 11 It may be.

[0565] Examples of a group combining an alicyclic hydrocarbon group and a chain hydrocarbon group include a group in which an alicyclic hydrocarbon group is bonded to a chain hydrocarbon group (e.g., *-chain hydrocarbon group-alicyclic hydrocarbon group-), a group in which a chain hydrocarbon group is bonded to an alicyclic hydrocarbon group (e.g., *-alicyclic hydrocarbon group-chain hydrocarbon group-), a group in which an alicyclic hydrocarbon group and a chain hydrocarbon group are bonded to a chain hydrocarbon group (e.g., *-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-), a group in which a chain hydrocarbon group and an alicyclic hydrocarbon group are bonded to an alicyclic hydrocarbon group (e.g., *-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-), a group in which an alicyclic hydrocarbon group, a chain hydrocarbon group, and an alicyclic hydrocarbon group are bonded to a chain hydrocarbon group (e.g., *-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-), a group in which a chain hydrocarbon group, an alicyclic hydrocarbon group, and a chain hydrocarbon group are bonded to an alicyclic hydrocarbon group (e.g., *-alicyclic hydrocarbon group-chain hydrocarbon group-alicyclic hydrocarbon group-chain hydrocarbon group-), and the like.

[0566] * represents the bonding site with X 11 and. Examples also include a group in which one or more hydrogen atoms of the above-described group are replaced with a bonding site. L 1 in the aliphatic hydrocarbon group having 1 to 28 carbon atoms of 2 -CH 2 - may be replaced with -O-, -S-, -SO

[0567] L 1 in the aliphatic hydrocarbon group having 1 to 28 carbon atoms of 2 -CH 2 - is replaced with -O-, -S-, -SO

[0568] -CH 2 - in the aliphatic hydrocarbon group is replaced with -O-, -S-, -SO 2 - or -CO-. Examples of the group include a hydroxy group (-CH contained in a methyl group) 2- is a group replaced by -O-), carboxy group (-CH contained in the ethyl group 2 -CH 2 - is a group replaced by -O-CO-), thiol group (-CH contained in the methyl group 2 - is a group replaced by -S-), alkoxy group (-CH at any position contained in the alkyl group 2 - is a group replaced by -O-), alkylthio group (-CH at any position contained in the alkyl group 2 - is a group replaced by -S-), alkoxycarbonyl group (-CH at any position contained in the alkyl group 2 -CH 2 - is a group replaced by -O-CO-), alkylsulfonyl group (-CH at any position contained in the alkyl group 2 - is replaced by -SO 2 -), alkylcarbonyl group (-CH at any position contained in the alkyl group 2 - is a group replaced by -CO-), alkylcarbonyloxy group (-CH at any position contained in the alkyl group 2 -CH 2 - is a group replaced by -CO-O-), oxy group (-CH contained in the methylene group 2 - is a group replaced by -O-), carbonyl group (-CH contained in the methylene group 2 - is a group replaced by -CO-), thio group (-CH contained in the methylene group 2 - is a group replaced by -S-), sulfonyl group (-CH contained in the methylene group 2 - is replaced by -SO 2 -), alkanedioxy group (-CH at any position contained in the alkanediyl group 2 - is a group replaced by -O-), alkanedioxycarbonyl group (-CH at any position contained in the alkanediyl group 2 -CH 2 - is a group replaced by -O-CO-), alkanediylcarbonyl group (-CH at any position contained in the alkanediyl group 2- is a group replaced by -CO-, an alkanediylcarbonyloxy group (a -CH at any position contained in the alkanediyl group) 2 -CH 2 - is a group replaced by -CO-O-, an alkanediylsulfonyl group (a -CH at any position contained in the alkanediyl group) 2 - is replaced by -SO 2 - is a group replaced by -SO-, an alkanediylthio group (a -CH at any position contained in the alkanediyl group) 2 - is a group replaced by -S-, a cycloalkoxy group, a cycloalkylalkoxy group, an alkoxycarbonyloxy group, a group formed by combining two or more of these groups, etc. Examples of these replaced groups include those similar to the groups exemplified in this specification within the range allowed by the upper limit of the number of carbon atoms.

[0569] Examples of the alkoxy group include alkoxy groups having 1 to 27 carbon atoms, such as 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 of the alkoxy group may be 1 to 17, preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0570] Examples of the alkylthio group include alkylthio groups having 1 to 27 carbon atoms, such as methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group, hexylthio group, octylthio group, 2-ethylhexylthio group, nonylthio group, decylthio group, undecylthio group, etc. The number of carbon atoms of the alkylthio group may be 1 to 17, preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0571] Examples of the alkoxycarbonyl group include alkoxycarbonyl groups having 2 to 27 carbon atoms, such as methoxycarbonyl group, ethoxycarbonyl group, butoxycarbonyl group and the like. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 28 carbon atoms, such as acetyl group, propionyl group and butyryl group and the like. Examples of the alkylcarbonyloxy group include alkylcarbonyloxy groups having 2 to 27 carbon atoms, such as acetyloxy group, propionyloxy group, butyryloxy group and the like. The number of carbon atoms of the alkoxycarbonyl group may be 2 to 17, preferably 2 to 11, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms of the alkylcarbonyl group may be 2 to 18, preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms of the alkylcarbonyloxy group may be 2 to 17, preferably 2 to 11, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3.

[0572] Examples of the alkylsulfonyl group include alkylsulfonyl groups having 1 to 27 carbon atoms, such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, octylsulfonyl group, 2-ethylhexylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, undecylsulfonyl group and the like. The number of carbon atoms of the alkylsulfonyl group may be 1 to 17, preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0573] Examples of the alkanediyl-oxy group include alkanediyl-oxy groups having 1 to 27 carbon atoms, such as a methylene-oxy group, an ethylene-oxy group, a propane-diyl-oxy group, a butane-diyl-oxy group, and a pentane-diyl-oxy group. The number of carbon atoms in the alkanediyl-oxy group may be 1 to 17, preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0574] Examples of the alkanediyl-oxycarbonyl group include alkanediyl-oxycarbonyl groups having 2 to 27 carbon atoms, such as a methylene-oxycarbonyl group, an ethylene-oxycarbonyl group, a propane-diyl-oxycarbonyl group, and a butane-diyl-oxycarbonyl group. Examples of the alkanediyl-carbonyl group include alkanediyl-carbonyl groups having 2 to 28 carbon atoms, such as a methylene-carbonyl group, an ethylene-carbonyl group, a propane-diyl-carbonyl group, a butane-diyl-carbonyl group, and a pentane-diyl-carbonyl group. Examples of the alkanediyl-carbonyloxy group include alkanediyl-carbonyloxy groups having 2 to 27 carbon atoms, such as a methylene-carbonyloxy group, an ethylene-carbonyloxy group, a propane-diyl-carbonyloxy group, and a butane-diyl-carbonyloxy group. The number of carbon atoms in the alkanediyl-oxycarbonyl group may be 2 to 17, preferably 2 to 11, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkanediyl-carbonyl group may be 2 to 18, preferably 2 to 12, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkanediyl-carbonyloxy group may be 2 to 17, preferably 2 to 11, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3.

[0575] Examples of the alkanediylthio group include alkanediylthio groups having 1 to 27 carbon atoms, such as a methylenethio group, an ethylenethio group, and a propanediylthio group. The number of carbon atoms in the alkanediylthio group may be 1 to 17, preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0576] Examples of the alkanediylsulfonyl group include alkanediylsulfonyl groups having 1 to 27 carbon atoms, such as a methylenesulfonyl group, an ethylenesulfonyl group, and a propylenesulfonyl group. The number of carbon atoms in the alkanediylsulfonyl group may be 1 to 17, preferably 1 to 11, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0577] Examples of the cycloalkoxy group include cycloalkoxy groups having 3 to 27 carbon atoms, such as a cyclohexyloxy group. Examples of the cycloalkylalkoxy group include cycloalkylalkoxy groups having 4 to 27 carbon atoms, such as a cyclohexylmethoxy group. Examples of the alkoxycarbonyloxy group include alkoxycarbonyloxy groups having 2 to 26 carbon atoms, such as a butoxycarbonyloxy group.

[0578] In addition, examples of the group in which -CH 2 - in the alicyclic hydrocarbon group is replaced by -O-, -S-, -CO- or -SO 2 - include the following groups. -O- or -CO- in the groups represented below may be replaced by -S- or -SO 2 -. The bonding site can be at any position.

[0579]

Chemical formula

[0580] L 1The aliphatic hydrocarbon group in [the compound] may have one or more substituents. Examples of the substituent include a halogen atom, a haloalkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms (the -CH 2 - in the alkyl group or the alicyclic hydrocarbon group may be replaced by -O- or -CO-).

[0581] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like. The haloalkyl group having 1 to 4 carbon atoms refers to a fluoroalkyl group having 1 to 4 carbon atoms, a chloroalkyl group having 1 to 4 carbon atoms, a bromoalkyl group having 1 to 4 carbon atoms, an iodoalkyl group having 1 to 4 carbon atoms, and the like. Examples of the haloalkyl group include a perfluoroalkyl group having 1 to 4 carbon atoms (such as a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a nonafluorobutyl group, etc.), a 2,2,2-trifluoroethyl group, a 3,3,3-trifluoropropyl group, a 4,4,4-trifluorobutyl group, a 3,3,4,4,4-pentafluorobutyl group, a chloromethyl group, a bromomethyl group, an iodomethyl group, and the like. The number of carbon atoms of the haloalkyl group is preferably 1 to 3, more preferably 1 or 2.

[0582] Examples of the alkyl group having 1 to 12 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, and the like. The number of carbon atoms of the alkyl group is preferably 1 to 9, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0583] Examples of the alicyclic hydrocarbon group having 3 to 18 carbon atoms include monocyclic cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclodecyl group, etc., and polycyclic cycloalkyl groups such as decahydronaphthyl group, adamantyl group, norbornyl group, etc. The number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 16, more preferably 3 to 12, and still more preferably 3 to 10.

[0584] Examples of the aromatic hydrocarbon group having 6 to 18 carbon atoms include phenyl group, naphthyl group, biphenyl group, anthryl group, phenanthryl group, binaphthyl group, etc. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 14, more preferably 6 to 12, and still more preferably 6 to 10.

[0585] -CH 2 - When - is replaced by -O- or -CO-, the number of carbon atoms before replacement is defined as the total number of carbon atoms of the alkyl group. Examples of the replaced group include hydroxy group (-CH 2 - in methyl group is replaced by -O-), carboxy group (-CH 2 -CH 2 - in ethyl group is replaced by -O-CO-), alkoxy group (-CH 2 - at any position in the alkyl group is replaced by -O-), alkoxycarbonyl group (-CH 2 -CH 2 - at any position in the alkyl group is replaced by -O-CO-), alkylcarbonyl group (-CH 2 - at any position in the alkyl group is replaced by -CO-), alkylcarbonyloxy group (-CH 2 -CH 2 - at any position in the alkyl group is replaced by -CO-O-), etc. These replaced groups include those similar to the groups exemplified in this specification within the range where the upper limit of the number of carbon atoms permits.

[0586] Examples of the alkoxy group include alkoxy groups having 1 to 11 carbon atoms, such as methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, undecyloxy group and the like. The number of carbon atoms of the alkoxy group is preferably 1 to 9, more preferably 1 to 6, still more preferably 1 to 4, and even more preferably 1 to 3.

[0587] Examples of the alkoxycarbonyl group include alkoxycarbonyl groups having 2 to 11 carbon atoms, such as methoxycarbonyl group, ethoxycarbonyl group, butoxycarbonyl group and the like. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 12 carbon atoms, such as acetyl group, propionyl group and butyryl group and the like. Examples of the alkylcarbonyloxy group include alkylcarbonyloxy groups having 2 to 11 carbon atoms, such as acetyloxy group, propionyloxy group, butyryloxy group and the like. The number of carbon atoms of the alkoxycarbonyl group is preferably 2 to 9, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms of the alkylcarbonyl group is preferably 2 to 10, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms of the alkylcarbonyloxy group is preferably 2 to 9, more preferably 2 to 6, still more preferably 2 to 4, and even more preferably 2 or 3.

[0588] L 1 Examples of the substituent which the aliphatic hydrocarbon group in L may have include a halogen atom, a haloalkyl group having 1 to 3 carbon atoms, an alkyl group having 1 to 6 carbon atoms, an alicyclic hydrocarbon group having 3 to 10 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms (in the alkyl group or the alicyclic hydrocarbon group, -CH 2 - may be replaced by -O- or -CO-). Fluorine atom, iodine atom, perfluoroalkyl group having 1 to 3 carbon atoms or alkyl group having 1 to 4 carbon atoms (in the alkyl group, -CH2 - may be replaced by -O- or -CO-. ) is more preferable, and a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, a hydroxy group or a methoxy group is even more preferable.

[0589] L 1 When not forming an alkyl fluoride group and an alicyclic hydrocarbon group of R 3 it may be a chain hydrocarbon group having 1 to 12 carbon atoms which may have a substituent (wherein -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-), an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (wherein -CH 2 - in the alicyclic hydrocarbon group may be replaced by -O- or -CO-), or a group formed by combining a chain hydrocarbon group having 1 to 6 carbon atoms which may have a substituent and an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (wherein -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-, and -CH 2 - in the alicyclic hydrocarbon group may be replaced by -O- or -CO-), preferably, it may be a chain hydrocarbon group having 1 to 8 carbon atoms which may have a substituent (wherein -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-), an alicyclic hydrocarbon group having 3 to 12 carbon atoms which may have a substituent, or a group formed by combining a chain hydrocarbon group having 1 to 6 carbon atoms which may have a substituent and an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (wherein -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-), more preferably, it may be a chain hydrocarbon group having 1 to 8 carbon atoms which may have a substituent (wherein -CH 2 - in the chain hydrocarbon group may be replaced by -O- or -CO-), an alicyclic hydrocarbon group having 5 to 12 carbon atoms which may have a substituent, or a group formed by combining a chain hydrocarbon group having 1 to 6 carbon atoms and an alicyclic hydrocarbon group having 5 to 12 carbon atoms which may have a substituent (wherein -CH 2- may be replaced by -O- or -CO. ) or a group formed by combining an alicyclic hydrocarbon group having 5 to 12 carbon atoms which may have a substituent, a chain hydrocarbon group having 1 to 6 carbon atoms, and an alicyclic hydrocarbon group having 5 to 12 carbon atoms which may have a substituent ( -CH contained in the chain hydrocarbon group 2 - is more preferably replaced by -O- or -CO. )

[0590] R 2 Examples of the alkyl fluoride group having 1 to 8 carbon atoms in R include difluoromethyl group, trifluoromethyl group, 1,1-difluoroethyl group, 2,2-difluoroethyl group, 2,2,2-trifluoroethyl group, perfluoroethyl group, 1,1,2,2-tetrafluoropropyl group, 1,1,2,2,3,3-hexafluoropropyl group, perfluoroethylmethyl group, 1-(trifluoromethyl)-1,2,2,2-tetrafluoroethyl group, perfluoropropyl group, 1,1,2,2-tetrafluorobutyl group, 1,1,2,2,3,3-hexafluorobutyl group, 1,1,2,2,3,3,4,4-octafluorobutyl group, perfluorobutyl group, 1,1-bis(trifluoro)methyl-2,2,2-trifluoroethyl group, 2-(perfluoropropyl)ethyl group, 1,1,2,2,3,3,4,4-octafluoropentyl group, perfluoropentyl group, 1,1,2,2,3,3,4,4,5,5-decafluoropentyl group, 1,1-bis(trifluoromethyl)-2,2,3,3,3-pentafluoropropyl group, perfluoropentyl group, 2-(perfluorobutyl)ethyl group, 1,1,2,2,3,3,4,4,5,5-decafluorohexyl group, 1,1,2,2,3,3,4,4,5,5,6,6-dodecafluorohexyl group, perfluoropentylmethyl group, perfluorohexyl group, perfluoroheptyl group, perfluorooctyl group. The number of carbon atoms of the alkyl fluoride group is preferably 1 to 6, more preferably 1 to 5, still more preferably 1 to 4, and even more preferably 1 to 3.

[0591] R 3The C1-C6 fluoroalkyl group in [description] is, as long as the upper limit of the number of carbon atoms permits, the same as the C1-C6 fluoroalkyl groups exemplified for the fluoroalkyl group of R 2 For the C1-C6 fluoroalkyl group of R R 2 is preferably a C1-C6 fluoroalkyl group, more preferably a C1-C3 fluoroalkyl group, still more preferably a trifluoromethyl group, a perfluoroethyl group or a perfluoropropyl group, and even more preferably a trifluoromethyl group when R 3 is a C1-C6 fluoroalkyl group.

[0592] R 2 is preferably a C1-C6 fluoroalkyl group, more preferably a C1-C5 fluoroalkyl group, still more preferably a C3-C5 fluoroalkyl group when R 3 is a hydrogen atom.

[0593] R 3 is bonded to L 1 to form a C3-C6 alicyclic hydrocarbon group, the group formed by the bonding of R 3 to L 1 includes, for example, the groups represented by the following formulas. Among the following formulas, * and ** represent the bonding sites, and the two ** represent that one represents the bonding site with a hydroxy group and the other represents the bonding site with R 2 ; L 1A is a part of the hydrocarbon group of L 1 and represents a single bond or a C1-C4 alkanediyl group. The number of carbon atoms of the alicyclic hydrocarbon group formed by the bonding of R 3 to L 1 is preferably 3-10, more preferably 3-8, and still more preferably 3-6.

[0594]

Chemical formula

[0595] R 3is preferably a hydrogen atom or an alkyl fluoride group having 1 to 3 carbon atoms. mi is preferably any integer from 1 to 3, more preferably 1 or 2, and even more preferably 1.

[0596] Examples of the structural unit (a4-A) include the following structural units.

[0597]

Chemical formula

[0598]

Chemical formula

[0599]

Chemical formula

[0600] In the above structural unit, the methyl group corresponding to R 1 is replaced with a hydrogen atom, a halogen atom, a haloalkyl group or an alkyl group other than a methyl group, and the hydrogen atom corresponding to R 1 is replaced with a halogen atom, a haloalkyl group or an alkyl group. Such structural units can also be cited as specific examples of the structural unit (a4-A).

[0601] When the resin (A) contains the structural unit (a4), its content is preferably 1 to 20 mol%, more preferably 2 to 15 mol%, and even more preferably 3 to 10 mol% based on all the structural units of the resin (A).

[0602] 〈Structural unit (a5)〉 Examples of the non-leaving hydrocarbon group of the structural unit (a5) include groups having a linear, branched or cyclic hydrocarbon group. Among them, the structural unit (a5) preferably has a group having an alicyclic hydrocarbon group.

[0603] Examples of the structural unit (a5) include a structural unit represented by the formula (a5-1).

[0604] [Chemical Formula]

[0605] [In the formula (a5-1), R 51 represents a hydrogen atom or a methyl group. R 52 represents an alicyclic hydrocarbon group having 3 to 18 carbon atoms, and the hydrogen atoms contained in the alicyclic hydrocarbon group may be substituted with aliphatic hydrocarbon groups having 1 to 8 carbon atoms.

[0606] L 55 represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH 2 - contained in the saturated hydrocarbon group may be replaced by -O- or -CO-. ]] R 52 The alicyclic hydrocarbon group in R may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. Examples of the polycyclic alicyclic hydrocarbon group include an adamantyl group and a norbornyl group.

[0607] Examples of the aliphatic hydrocarbon group having 1 to 8 carbon atoms include alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group, and a 2-ethylhexyl group.

[0608] Examples of the alicyclic hydrocarbon group having a substituent include a 3-methyladamantyl group. R 52 is preferably an unsubstituted alicyclic hydrocarbon group having 3 to 18 carbon atoms, more preferably an adamantyl group, a norbornyl group, or a cyclohexyl group.

[0609] L55 Examples of the divalent saturated hydrocarbon group in [compound name] include a divalent chain saturated hydrocarbon group and a divalent alicyclic saturated hydrocarbon group, preferably a divalent chain saturated hydrocarbon group. Examples of the divalent chain saturated hydrocarbon group include alkane diyl groups such as a methylene group, an ethylene group, a propane diyl group, a butane diyl group, and a pentane diyl group.

[0610] The divalent alicyclic saturated hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic saturated hydrocarbon group include cycloalkane diyl groups such as a cyclopentane diyl group and a cyclohexane diyl group. Examples of the polycyclic divalent alicyclic saturated hydrocarbon group include an adamantane diyl group and a norbornane diyl group.

[0611] L 55 In the divalent saturated hydrocarbon group represented by [compound name], examples of the group in which -CH 2 - is replaced by -O- or -CO- include groups represented by formula (L1-1) to formula (L1-4). In the following formulas, * and ** each represent a bonding site, and * represents a bonding site with an oxygen atom.

[0612]

Chemical formula

[0613] [In formula (L1-1), X x1 represents *-O-CO- or *-CO-O- (* represents a bonding site with L x1 ).).

[0614] L x1 represents a divalent aliphatic saturated hydrocarbon group having 1 to 16 carbon atoms. L x2 represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 15 carbon atoms. However, the total number of carbon atoms of L x1 and L x2 is 16 or less.

[0615] In formula (L1-2), L x3 represents a divalent aliphatic saturated hydrocarbon group having 1 to 17 carbon atoms. L x4 represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 16 carbon atoms.

[0616] However, the total number of carbon atoms of L x3 and L x4 is 17 or less. In formula (L1-3), L x5 represents a divalent aliphatic saturated hydrocarbon group having 1 to 15 carbon atoms.

[0617] L x6 and L x7 each independently represent a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 14 carbon atoms. However, the total number of carbon atoms of L x5 、L x6 and L x7 is 15 or less.

[0618] In formula (L1-4), L x8 and L x9 each represent a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 12 carbon atoms.

[0619] W x1 represents a divalent alicyclic saturated hydrocarbon group having 3 to 15 carbon atoms. However, the total number of carbon atoms of L x8 、L x9 and W x1 is 15 or less. L x1 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group.

[0620] L x2 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a single bond. L x3 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms.

[0621] L x4 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x5 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group.

[0622] L x6 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group. L x7 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms.

[0623] L x8 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a single bond or a methylene group. L x9 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a single bond or a methylene group.

[0624] W x1 is preferably a divalent alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms, more preferably a cyclohexanediyl group or an adamantanediyl group. Examples of the group represented by the formula (L1-1) include the following divalent groups.

[0625]

Chemical formula

[0626] Examples of the group represented by the formula (L1-2) include the following divalent groups.

[0627]

Chemical formula

[0628] Examples of the group represented by formula (L1-3) include the following divalent groups.

[0629] [Chemical formula]

[0630] Examples of the group represented by formula (L1-4) include the following divalent groups.

[0631] [Chemical formula]

[0632] L 55 is preferably a single bond or a group represented by formula (L1-1). Examples of the structural unit (a5-1) include the following structural units and structural units in which the methyl group corresponding to R in the following structural unit (a5-1) is replaced by a hydrogen atom. 51

[0633] [Chemical formula]

[0634] When the resin (A) contains the structural unit (a5), its content is preferably 1 to 30 mol%, more preferably 2 to 20 mol%, and still more preferably 3 to 15 mol% with respect to all the structural units of the resin (A).

[0635] 〈Structural unit (a6)〉 The structural unit (a6) is a structural unit having a -SO 2 - group, and preferably has a -SO 2 - group in the side chain.

[0636] -SO 2 The structural unit having a - group may have a linear structure having a -SO 2 - group, or -SO 2It may have a branched structure having a - group, or -SO 2 It may have a cyclic structure (monocyclic and polycyclic structures) having a - group. Preferably, -SO 2 It is a structural unit having a cyclic structure having a - group, and more preferably, -SO 2 It is a structural unit having a cyclic structure (sultone ring) containing -O-.

[0637] Examples of the sultone ring include the following formula (T 1 -1), formula (T 1 -2), formula (T 1 -3) and formula (T 1 -4). The bonding site can be at any position. The sultone ring may be monocyclic, but is preferably polycyclic. The polycyclic sultone ring means a bridged ring containing -SO 2 -O-, and examples include the rings represented by formula (T 1 -1) and formula (T 1 -2). The sultone ring may further contain a heteroatom in addition to -SO 1 -O- as an atomic group constituting the ring, like the ring represented by formula (T 2 -2). Examples of the heteroatom include an oxygen atom, a sulfur atom or a nitrogen atom, and preferably an oxygen atom.

[0638]

Chemical formula

[0639] The sultone ring may have a substituent, and examples of the substituent include an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group, a halogen atom, a hydroxy group, a cyano group, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a glycidyloxy group, an alkoxycarbonyl group having 2 to 12 carbon atoms, and an alkylcarbonyl group having 2 to 4 carbon atoms, etc.

[0640] 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, and more preferably a methyl group.

[0641] 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. Preferably, a trifluoromethyl group is included.

[0642] Examples of the alkyl group having a hydroxy group include a hydroxymethyl group and a hydroxyalkyl group such as 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.

[0643] 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.

[0644] 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 a group in which an alkoxy group such as a methoxycarbonyl group and an ethoxycarbonyl group is bonded to a carbonyl group. Preferably, an alkoxycarbonyl group having 6 or less carbon atoms is included, and more preferably a methoxycarbonyl group is included.

[0645] Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, and a butyryl group. From the viewpoint that the production of the monomer leading to the structural unit (a6) is easy, a sultone ring having no substituent is preferred.

[0646] As the sultone ring, a ring represented by the following formula (T1′) is preferred.

[0647] [Chemical formula]

[0648] [In the formula (T1′), X 11 represents an oxygen atom, a sulfur atom, or a methylene group. R 41 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.

[0649] ma represents any integer from 0 to 9. When ma is 2 or more, a plurality of R 41 may be the same or different. The bonding site is at an arbitrary position. ] X 11 is preferably an oxygen atom or a methylene group, more preferably a methylene group.

[0650] R 41 is the same as the substituent of the sultone ring, and an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group is preferred. ma is preferably 0 or 1, more preferably 0.

[0651] Examples of the ring represented by formula (T1') include the following rings. The bonding site can be at any position. Among them, those in which the bonding site is at the 1-position or 3-position are preferred.

[0652]

Chemical formula

[0653] -SO 2 The structural unit having a - group preferably further has a group derived from a polymerizable group. Examples of the polymerizable group include a vinyl group, an acryloyl group, a methacryloyl group, an acryloyloxy group, a methacryloyloxy group, an acryloylamino group, a methacryloylamino group, an acryloylthio group, a methacryloylthio group, and the like.

[0654] Among them, the monomer that leads to the structural unit (a6) is preferably a monomer having an ethylenically unsaturated bond, and more preferably a (meth)acrylic monomer. The structural unit (a6) is preferably a structural unit represented by formula (a6-0).

[0655]

Chemical formula

[0656] [In formula (a6-0), R x represents an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, a hydrogen atom or a halogen atom.

[0657] A xx represents an oxygen atom, -N(R c )- or a sulfur atom. A x represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH 2 - contained in the saturated hydrocarbon group may be replaced by -O-, -CO- or -N(R d )-.

[0658] X11 represents an oxygen atom, a sulfur atom or a methylene group. R 41 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.

[0659] ma represents any integer from 0 to 9. When ma is 2 or more, a plurality of R 41 may be the same or different. R c and R d each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R x Examples of the halogen atom of R include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

[0660] R x Examples of the alkyl group of R include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group and an n-hexyl group, etc. Preferably, it is an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group.

[0661] R x Examples of the alkyl group having a halogen atom of R 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, etc.

[0662] R xis 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 still more preferably a hydrogen atom or a methyl group. A x Examples of the divalent saturated hydrocarbon group of A include a linear alkanediyl group, a branched alkanediyl group, a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, and a combination of two or more of these groups may also be used.

[0663] Specifically, linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, tridecane-1,13-diyl group, tetradecane-1,14-diyl group, pentadecane-1,15-diyl group, hexadecane-1,16-diyl group, heptadecane-1,17-diyl group, ethane-1,1-diyl group, propane-1,1-diyl group and propane-2,2-diyl group; branched alkanediyl groups such as butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group; monocyclic divalent alicyclic saturated hydrocarbon groups which are cycloalkanediyl groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclooctane-1,5-diyl group; polycyclic divalent alicyclic saturated hydrocarbon groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group and the like can be mentioned.

[0664] A x The bonding position to the sultone ring of A can be any position, but the one at the 1-position is preferred. Examples of the structural unit (a6-0) include the following structural units.

[0665] [Chemical formula]

[0666] Among them, the structural units represented by formula (a6-1), formula (a6-2), formula (a6-6), formula (a6-7), formula (a6-8) and formula (a6-12) are preferred, and the structural units represented by formula (a6-1), formula (a6-2), formula (a6-7) and (a6-8) are more preferred.

[0667] When the resin (A) contains the structural unit (a6), its content is preferably 1 to 50 mol%, more preferably 2 to 40 mol%, and still more preferably 3 to 30 mol% based on all the structural units of the resin (A).

[0668] <Structural unit (a7)> The resin (A) etc. may further contain a structural unit that decomposes upon exposure to generate an acid (hereinafter sometimes referred to as "structural unit (a7)"). Specific examples of the structural unit (a7) include the structural units described in JP-A-2016-79235, and it is preferably a structural unit having a sulfonate group or a carboxylate group and an organic cation in the side chain or a structural unit having a sulfonio group and an organic anion in the side chain.

[0669] The structural unit having a sulfonate group or a carboxylate group and an organic cation in the side chain is preferably a structural unit represented by formula (a7-A).

[0670] [Chemical formula]

[0671] [In formula (a7-A), R a7 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom.

[0672] X a71represents a single bond, *-O-*, *-CO-O-*, *-O-CO-O-*, *-CO-NR a71 -*, *-NR a71 -CO-O-*, *-O-CO-NR a71 -* or *-Ax-Ph-Ay-*.

[0673] R a71 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ph represents a phenylene group which may have a substituent. Ax and Ay each independently represent one or more bond types selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, an amide bond, and a carbonate bond.

[0674] * and ** represent bonding sites, and * represents the bonding site with the carbon atom to which R a7 is bonded. L a71 and L a72 each independently represent a hydrocarbon group having 1 to 24 carbon atoms which may have a substituent, and -CH 2 - in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO 2 -.

[0675] X a72 represents ***-CO-O-, ***-O-CO-, ***-O-CO-O-, ***-O-, and *** represents the bonding site with L a71 is bonded. na7 represents any integer from 0 to 2. When na7 is 2, the groups in the plurality of parentheses may be the same as or different from each other.

[0676] RA - represents a sulfonate anion or a carboxyl anion. ZA + represents an organic cation. R a7 The halogen atom and the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in R are R of formula (a1-0), formula (a1-1) and formula (a1-2).a01 , R a4 and R a5 include those similar to those exemplified by

[0677] R a7 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, still more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group.

[0678] X a71 When it is a group represented by *-Ax-Ph-Ay-**, it is preferably a linking group represented by the following formula (X10).

[0679] [Chemical formula]

[0680] [In formula (X10), Ax represents a bonding type that binds to the carbon atom to which R a7 is bonded, and represents one or more bonding types selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, a carbonate ester bond, and an amide bond.

[0681] Ay represents a bonding type that binds to L a71 and represents one or more bonding types selected from the group consisting of a single bond, an ether bond, a thioether bond, an ester bond, a carbonate ester bond, and an amide bond.

[0682] Rx represents a halogen atom, a hydroxy group, a fluorinated alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. mx represents any integer from 0 to 4, and when mx is an integer of 2 or more, the plurality of Rx may be the same or different from each other.] When either Ax or Ay is a single bond, the other is preferably at least one selected from the group consisting of an ether bond, a thioether bond, an ester bond, a carbonate ester bond, and an amide bond.

[0683] When either of Ax and Ay is an amide bond, it is preferably a bond represented by -CO-NR a71 -. The bonding position of Ay in the phenylene group is preferably the meta or para position with respect to the bonding position of Ax, and more preferably the para position.

[0684] Among others, Rx is preferably a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, or an ethyl group. mx is preferably 0, 1, or 2.

[0685] X a71 Examples of X 10 -1) to the group represented by the formula (X 10 -10). * represents the bonding site with the carbon atom to which -R a7 is bonded. ** represents the bonding site with L a71 . X 20 represents -O- or -NR a71 -.

[0686]

Chemical formula

[0687] Specific examples of the group represented by the formula (X 10 -1) to the formula (X 10 -10) include the following groups.

[0688]

Chemical formula

[0689] Among others, X a71 is a single bond and the formula (X 10 -1′), the formula (X10 -3′), a group represented by formula (X 10 -9′), preferably a single bond or a group represented by formula (X 10 -1′), formula (X 10 -4′), formula (X 10 -5′), formula (X 10 -6′), and formula (X 10 -9′), more preferably a single bond, a group represented by formula (X 10 -1′), a group represented by formula (X 10 -5′), a group represented by formula (X 10 -6′), or a group represented by formula (X 10 -9′).

[0690] L a71 As the hydrocarbon group of, a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining two or more of these groups, with one hydrogen atom removed, a group that binds X a71 and X a72 and the group that binds. Also, as the hydrocarbon group of L a72 a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining two or more of these groups, with one hydrogen atom removed, a group that binds X a72 and RA - and the group that binds.

[0691] L a71 and L a72Examples of the chain hydrocarbon group include a group obtained by removing one hydrogen atom from an alkyl group or an alkenyl group. The alkyl group may be linear or branched, and specific examples include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, sec-butyl group, iso-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, heptadecyl group, and the like. Examples of the alkenyl group include ethenyl group, propenyl group, isopropenyl group, butenyl group, isobutenyl group, tert-butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, isooctenyl group, nonenyl group, and the like.

[0692] The number of carbon atoms in the chain hydrocarbon group is preferably 1 to 20, more preferably 1 to 18, and even more preferably 1 to 10. L a71 and L a72 Examples of the alicyclic hydrocarbon group of L and L include a group obtained by removing one hydrogen atom from a monocyclic or polycyclic cycloalkyl group. Examples of the monocyclic cycloalkyl group include cyclobutyl group, cycloheptyl group, cyclohexyl group, cyclopentyl group, cyclooctyl group, and the like.

[0693] L a71 and L a72Examples of the polycyclic cycloalkyl group include a cycloalkyl group having a crosslinked structure, a cycloalkyl group in which two or more rings are condensed, or a cycloalkyl group in which two rings are spiro-bonded. Examples of the cycloalkyl group having a crosslinked structure include a norbornyl group and an adamantyl group. Examples of the cycloalkyl group in which two or more rings are condensed include a bicyclo[4,4,0]decane group and a steroid group (steroid skeleton). Examples of the cycloalkyl group in which two rings are spiro-bonded include a spirocycloalkyl group in which one cycloalkyl group selected from the group consisting of a cyclopentyl group, a cyclohexyl group, a norbornyl group, and an adamantyl group and a cycloalkyl group having 5 to 8 carbon atoms are spiro-bonded. A double bond may be formed between two carbon atoms contained in the alicyclic hydrocarbon group. More specifically, examples of the alicyclic hydrocarbon group represented by the following formula can be given.

[0694] [Chemical formula]

[0695] When the alicyclic hydrocarbon group is a monocyclic cycloalkyl group, the number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 18, more preferably 3 to 12, and even more preferably 3 to 8. When the alicyclic hydrocarbon group is a polycyclic cycloalkyl group, the number of carbon atoms in the alicyclic hydrocarbon group is preferably 6 to 18, and more preferably 7 to 12.

[0696] L a71 and L a72 Examples of the aromatic hydrocarbon group of L

[0697] L a71 and L a72-CH contained in the hydrocarbon group 2 - is replaced by -O-, -CO-, -S- or -SO 2 - When replaced, the number of carbon atoms before replacement shall be the number of carbon atoms of the hydrocarbon group.

[0698] L a71 and L a72 Among the hydrocarbon groups of L 2 -CH contained in the chain hydrocarbon group 2 - When replaced by -O-, -CO-, -S- or -SO

[0699] L a71 and L a72 Among the hydrocarbon groups of L 2 -CH contained in the alicyclic hydrocarbon group 2 - When replaced by -O-, -CO-, -S- or -SO

[0700]

Chemical formula

[0701] L a71 and L a72 Among the hydrocarbon groups of L 2 -CH may be replaced by -O- or -S-, -CH 2-As the group replaced by -O- or -S-, groups derived from a furan ring or a thiophene ring, etc. may be mentioned respectively.

[0702] L a71 and L a72 As the group combining two or more groups of the chain hydrocarbon group, alicyclic hydrocarbon group and aromatic hydrocarbon group of L a71 and L a72 , groups combining the above chain hydrocarbon group and the above alicyclic hydrocarbon group, groups combining the above chain hydrocarbon group and the above aromatic hydrocarbon group, groups combining the above alicyclic hydrocarbon group and the above aromatic hydrocarbon group, and groups combining the above chain hydrocarbon group, the above alicyclic hydrocarbon group and the above aromatic hydrocarbon group may be mentioned. As the group combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group, a condensed ring may be acceptable.

[0703] L a71 and L a72 As the substituent that the hydrocarbon group of L a71 and L a72 may have, a halogen atom, a cyano group, and a nitro group may be mentioned. As the halogen atom, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. may be mentioned.

[0704] L a71 and L a72 When L a71 and L a72 are a group combining an alicyclic hydrocarbon group or an aromatic hydrocarbon group and a chain hydrocarbon group, substantially, the chain hydrocarbon group may be regarded as a substituent that the alicyclic hydrocarbon group or the aromatic hydrocarbon group has. Also, a71 and L a72 -CH 2 - of the chain hydrocarbon group contained in the hydrocarbon group of L a71 and L a72 is replaced by -O-, -CO-, -S- or -SO 2 -, whereby the hydrocarbon group of L a71 and L a72 can substantially have substituents such as a hydroxy group, a carboxy group, an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group, an alkylcarbonyloxy group, a thiol group, a sulfonyl group, etc. a71 and L a72

[0705] na7 is preferably 0 or 1. ZA in formula (a7-A) +Examples thereof include the same as the cation in the salt represented by the formula (B1) or the like.

[0706] In the formula (a7-A), L a71 and L a72 When the hydrocarbon group is a saturated hydrocarbon group, in the formula (a7-B) described later, A b7 may contain a group similar to the group exemplified as the divalent linking group of.

[0707] Examples of the structural unit represented by the formula (a7-A) include the structural unit represented by the formula (a7-A1) and the like.

[0708] [Chemical formula]

[0709] [In the formula (a7-A1), R a7 , X a71 , L a71 , X a72 , na7, RA - and ZA + represent the same meaning as above.

[0710] z7 represents any integer from 0 to 6. Q a7 , Q b7 , R z71 and R z72 each independently represent 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. When z7 is 2 or more, a plurality of R z71 and R z72 may be the same as or different from each other.] Q a7 , Q b7 , R z71 and R z72 Examples of the perfluoroalkyl group having 1 to 6 carbon atoms or the alkyl group having 1 to 6 carbon atoms in include the same groups as those exemplified for R a7 .

[0711] Examples of the structural unit represented by the formula (a7-A) include the following structural units, R a7 structural units in which the group corresponding to the methyl group of a7 is replaced by a hydrogen atom, a halogen atom (for example, a fluorine atom), or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom (for example, a trifluoromethyl group, etc.), and the structural units described in International Publication No. 2012 / 050015. ZA + represents an organic cation.

[0712]

Chemical formula

[0713]

Chemical formula

[0714] The structural unit having a sulfonio group and an organic anion in the side chain is preferably a structural unit represented by the formula (a7-B).

[0715]

Chemical formula

[0716] [In the formula (a7-B), R a7 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom.

[0717] A b7 represents a single bond or a divalent linking group. R b71 represents a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent. R b72 and R b73 each independently represent a hydrocarbon group having 1 to 18 carbon atoms which may have a substituent, and R b72 and R b73 may be bonded to each other to form a ring together with the sulfur atom to which they are bonded.

[0718] A - represents an organic anion. R a7 Examples of the halogen atom and the alkyl group which may have a halogen atom of R include the same halogen atom and the alkyl group which may have a halogen atom as those of formula (a7-A).

[0719] R b71 Examples of the divalent aromatic hydrocarbon group having 6 to 18 carbon atoms represented by R include a phenylene group and a naphthylene group. R b72 and R b73 Examples of the hydrocarbon group represented by R include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these.

[0720] Examples of the alkyl group, the alicyclic hydrocarbon group, the aromatic hydrocarbon group, and the group formed by combining these are the same as those described above. A b7 Examples of the divalent linking group represented by A include a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH 2 - included in the divalent saturated hydrocarbon group may be replaced by -O-, -S- or -CO-.

[0721] Examples of the divalent saturated hydrocarbon group include a divalent chain-like saturated hydrocarbon group such as a linear or branched alkanediyl group, and a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, and combinations thereof may also be used.

[0722] Specifically, linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group; branched alkanediyl groups such as butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group; divalent monocyclic alicyclic saturated hydrocarbon groups which are monocyclic cycloalkanediyl groups such as cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexane-1,4-diyl group, cyclooctane-1,5-diyl group; divalent polycyclic alicyclic saturated hydrocarbon groups which are polycyclic cycloalkanediyl groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, etc. are included.

[0723] -CH contained in the saturated hydrocarbon group 2 - replaced by -O-, -S- or -CO- includes, for example, the following divalent groups. However, the number of carbon atoms before -CH 2 - is replaced by -O-, -S- or -CO- is 17 or less respectively. In the following formula, * and ** represent bonding sites, and * represents the bonding site with R b71 and the bonding site with.

[0724]

Chemical formula

[0725] [In the formula, X 3 represents a divalent saturated hydrocarbon group having 1 to 16 carbon atoms. X 4 represents a divalent saturated hydrocarbon group having 1 to 15 carbon atoms. X 5 represents a divalent saturated hydrocarbon group having 1 to 13 carbon atoms.

[0726] X 6 represents a divalent saturated hydrocarbon group having 1 to 14 carbon atoms. X 7 represents a trivalent saturated hydrocarbon group having 1 to 14 carbon atoms. X 8 represents a divalent saturated hydrocarbon group having 1 to 13 carbon atoms. As the structural unit containing the cation in the formula (a7-B), there are a structural unit represented by the following and a group corresponding to the methyl group of R a7 in which the methyl group is replaced by a hydrogen atom, a halogen atom (for example, a fluorine atom) or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom (for example, a trifluoromethyl group, etc.), and the like.

[0727]

Chemical formula

[0728] A - Examples of the organic anion represented by A include a sulfonate anion, a sulfonylimide anion, a sulfonylmethide anion, and a carboxylate anion. A - The organic anion represented by A is preferably a sulfonate anion, and more preferably the same as the anion exemplified by the acid generator (B). Examples of the sulfonylimide anion, the sulfonylmethide anion, and the carboxylate anion are the same as the anions exemplified by the acid generator (B).

[0729] Examples of the structural unit represented by the formula (a7-B) include a structural unit represented by the following.

[0730]

Chemical formula

[0731] When the resin (A) contains the structural unit (a7), the structural unit (a7) may be contained alone or in combination of two or more. The content of the total structural unit (a7) is preferably 1 to 30 mol%, more preferably 2 to 25 mol%, still more preferably 3 to 20 mol% based on all the structural units of the resin (A).

[0732] The resin (A) is preferably a resin composed of the structural unit (I), the structural unit (II) and the structural unit (a1), or a resin composed of the structural unit (I), the structural unit (II), the structural unit (a1) and the structural unit (s).

[0733] The structural unit (a1) is preferably at least one selected from the group consisting of the structural unit (a1-0), the structural unit (a1-1) and the structural unit (a1-2) (preferably the structural unit having a cyclohexyl group or a cyclopentyl group), more preferably at least one selected from the group consisting of the structural unit (a1-1) and the structural unit (a1-2).

[0734] The structural unit (s) is preferably at least one selected from the group consisting of the structural unit (a2) and the structural unit (a3). The structural unit (a2) is preferably the structural unit (a2-1) or the structural unit (a2-A). The structural unit (a3) is preferably at least one selected from the group consisting of the structural unit represented by the formula (a3-1), the structural unit represented by the formula (a3-2) and the structural unit represented by the formula (a3-4).

[0735] Each structural unit constituting the resin (A) may be used alone or in combination of two or more, and can be produced by a known polymerization method (for example, radical polymerization method) using the monomers that lead to these structural units. The content of each structural unit of the resin (A) can be adjusted by the amount of the monomers used in the polymerization.

[0736] The weight average molecular weight of resin (A) is preferably 2,000 or more (more preferably 2,500 or more, still more preferably 3,000 or more) and 50,000 or less (more preferably 30,000 or less, still more preferably 15,000 or less), but may contain oligomers having a weight average molecular weight smaller than this. In the present specification, the weight average molecular weight is a value determined by gel permeation chromatography under the conditions described in the examples.

[0737] <Resins other than resin (A)> The resist composition of the present invention may contain a resin other than resin (A). The resin other than resin (A) is a resin that does not contain either structural unit (I) or structural unit (II), and examples thereof include a resin composed only of structural unit (s), a resin composed of structural units derived from structural unit (a1), structural unit (a2), structural unit (a3) and / or other known monomers, a resin composed of structural units derived from structural unit (I), structural unit (a1), structural unit (a2), structural unit (a3) and / or other known monomers, and a resin composed of structural units derived from structural unit (II), structural unit (a1), structural unit (a2), structural unit (a3) and / or other known monomers.

[0738] Examples of other resins also include resins containing structural unit (a4) or structural unit (a5) (however, they do not contain structural unit (I), structural unit (II) and structural unit (a1), and may hereinafter be referred to as "resin (X)").

[0739] As resin (X), among others, a resin containing structural unit (a4) is preferable. When the resin (X) contains the structural unit (a4), in the resin (X), the content of the structural unit (a4) is 20 mol% or more, preferably 30 mol% or more, more preferably 40 mol% or more, and still more preferably 45 mol% or more, based on the total of all the structural units of the resin (X). Further, it is 100 mol% or less, preferably 80 mol% or less, more preferably 70 mol% or less, still more preferably 60 mol% or less, and even more preferably 55 mol% or less. Specifically, 20 to 100 mol% is mentioned, preferably 20 to 80 mol%, more preferably 30 to 70 mol%, still more preferably 40 to 60 mol%, and even more preferably 45 to 55 mol%. When the resin (X) contains the structural unit (a5), the content of the structural unit (a5) is 20 mol% or more, preferably 30 mol% or more, more preferably 40 mol% or more, and still more preferably 45 mol% or more, based on the total of all the structural units of the resin (X). Further, it is 100 mol% or less, preferably 80 mol% or less, more preferably 70 mol% or less, still more preferably 60 mol% or less, and even more preferably 55 mol% or less. Specifically, 20 to 100 mol% is mentioned, preferably 20 to 80 mol%, more preferably 30 to 70 mol%, still more preferably 40 to 60 mol%, and even more preferably 45 to 55 mol%. Further, when the resin (X) contains the structural unit (a4) and the structural unit (a5), the total content of the structural unit (a4) and the structural unit (a5) is 40 mol% or more, preferably 60 mol% or more, more preferably 70 mol% or more, and still more preferably 80 mol% or more, based on the total of all the structural units of the resin (X). Further, it is 100 mol% or less. Specifically, 40 to 100 mol% is mentioned, preferably 60 to 100 mol%, more preferably 70 to 100 mol%, and still more preferably 80 to 100 mol%.

[0740] Examples of the structural unit that the resin (X) may further have include the structural unit (a2), the structural unit (a3), and the structural unit derived from other known monomers. Among them, the resin (X) is preferably a resin composed of only the structural unit (a4) and / or the structural unit (a5).

[0741] Each structural unit constituting the resin (X) may be used alone or in combination of two or more, and can be produced by a known polymerization method (for example, radical polymerization method) using the monomers that induce these structural units. The content of each structural unit of the resin (X) can be adjusted by the amount of monomers used in the polymerization.

[0742] Each structural unit constituting the resin (X) may be used alone or in combination of two or more, and can be produced by a known polymerization method (for example, radical polymerization method) using the monomers that induce these structural units. The content of each structural unit of the resin (X) can be adjusted by the amount of monomers used in the polymerization.

[0743] The weight average molecular weight of the resin (X) is preferably 6,000 or more (more preferably 7,000 or more) and 80,000 or less (more preferably 60,000 or less), but may contain oligomers having a weight average molecular weight smaller than this. The measuring means for the weight average molecular weight of the resin (X) is the same as that of the resin (A).

[0744] When the resist composition of the present invention contains the resin (X), its content is preferably 1 to 60 parts by mass, more preferably 1 to 50 parts by mass, still more preferably 1 to 40 parts by mass, even more preferably 1 to 30 parts by mass, and even more preferably 1 to 8 parts by mass with respect to 100 parts by mass of the resin (A).

[0745] The content rate of the resin (A) in the resist composition is preferably 20 mass% or more and 100 mass% or less, more preferably 50 mass% or more and 99 mass% or less, based on the solid content of the resist composition. Further, when the resist composition contains a resin other than the resin (A), the total content rate of the resin (A) and the resin other than the resin (A) is preferably 60 mass% or more and 100 mass% or less, more preferably 70 mass% or more and 99 mass% or less, still more preferably 80 mass% or more and 99 mass% or less, and even more preferably 90 mass% or more and 99 mass% or less, based on the solid content of the resist composition. The solid content of the resist composition and the content rate of the resin relative thereto can be measured by known analysis means such as liquid chromatography or gas chromatography.

[0746] <Acid generator (B)> As the acid generator (B), either a nonionic compound or an ionic compound may be used. Examples of the nonionic compound include sulfonate esters (e.g., 2-nitrobenzyl ester, aromatic sulfonate, oxime sulfonate, N-sulfonyloxyimide, sulfonyloxy ketone, diazonaphthoquinone 4-sulfonate), sulfones (e.g., disulfone, ketosulfone, sulfonyldiazomethane), and the like. Representative examples of the ionic compound include onium salts containing an onium cation (e.g., diazonium salt, phosphonium salt, sulfonium salt, iodonium salt). Examples of the anion of the onium salt include sulfonic acid anion, benzenesulfonyl anion, sulfonylimide anion, sulfonylmethide anion, and carboxylic acid anion.

[0747] The acid generator (B) may be a part of the structural unit constituting the resin contained in the resist composition of the present invention, such as the above-mentioned structural unit (a7). As t...

Claims

1. A resist composition comprising a resin that includes a structural unit represented by formula (I) and a structural unit having a group represented by formula (II-x). 【Chemistry 1】 [In formula (I), X ０ represents a single bond or a hydrocarbon group having 1 to 72 carbon atoms which may have a substituent, and —CH ２ - is -O-, -S-, -CO- or -SO ２ It may be replaced with -. L １０ represents a single bond or a hydrocarbon group having 1 to 36 carbon atoms which may have a substituent, and —CH ２ - is -O-, -S-, -SO ２ It may be replaced by --or --CO--. R １０ represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. X １０ represents a single bond, *-O-**, *-CO-O-**, *-O-CO-O-**, *-CO-NR ９ -**, *-NR ９ -CO-O-**, *-O-CO-NR ９ -** or *-Ax-Ph-Ay-**. R ９ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. Ph represents a phenylene group which may have a substituent. Ax and Ay each independently represent one or more bond types selected from the group consisting of a single bond, an ether bond, a thioether bond, an amide bond, an ester bond, and a carbonate bond. * and ** represent binding sites, * represents R １０ represents the bonding site with the carbon atom to which it is bonded. R ３ , R ４ , R ５ and R ６ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH ２ - is -O-, -S-, -NR ７ -, -SO ２ may be replaced by - or -CO-, R ３ and R ４ , R ５ and R ６ Or R ３ and R ４ and R ５ may be bonded to each other to form a cyclic hydrocarbon group having 3 to 20 carbon atoms, and the cyclic hydrocarbon group may have one or more double bonds between two adjacent carbon atoms, and the -CH ２ - is -O-, -CO- or -NR ７ - may be substituted, and -CH= contained in the cyclic hydrocarbon group may be substituted with -N=. R ７ represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and the —CH ２ - is -O-, -S-, -SO ２ - or -CO- may be substituted.] 【Chemistry 2】 [In formula (II-x), Ring W １ represents a heterocycle having 2 to 36 carbon atoms, a hydrogen atom contained in the heterocycle may be substituted with a halogen atom or a hydrocarbon group having 1 to 24 carbon atoms, and —CH ２ - is -O-, -S-, -CO- or -NR ｃ It may be substituted with a - group. R ｃ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. * indicates a binding site.

2. X １０ is a single bond or a group represented by the formula (X １０ -1) ~Formula (X １０ 2. The resist composition according to claim 1, wherein the aryl group is a group represented by any one of the following formulas: 【Chemistry 3】 [Formula (X １０ -1) ~ Type (X １０ -10) *, ** are binding sites, * is R １０ represents the bonding site with the carbon atom to which it is bonded. Rx represents a halogen atom, a hydroxy group, a fluorinated alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 18 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. mx represents an integer of 0 to 4. X ２０ is -O- or -NR ９ Represents -. R ９ has the same meaning as in formula (I).

3. L １０ is a single bond, a chain hydrocarbon group having 1 to 10 carbon atoms which may have a substituent (provided that the —CH ２ - may be replaced by -O- or -CO-), a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent (provided that the -CH ２ - is -O-, -S-, -CO- or -SO ２ -) or a group formed by combining a chain hydrocarbon group having 1 to 8 carbon atoms which may have a substituent and a cyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent (with the proviso that -CH ２ - may be replaced by -O- or -CO-, and -CH contained in the cyclic hydrocarbon group ２ - is -O-, -S-, -SO ２ 2. The resist composition according to claim 1, wherein:

4. X ０ is a single bond, an open chain hydrocarbon group having 1 to 18 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, a group in which an alicyclic hydrocarbon group having 3 to 36 carbon atoms and an open chain hydrocarbon group having 1 to 18 carbon atoms are combined, an aromatic hydrocarbon group having 6 to 36 carbon atoms, or a group in which an aromatic hydrocarbon group having 6 to 36 carbon atoms and an open chain hydrocarbon group having 1 to 18 carbon atoms are combined, The —CH group contained in the chain hydrocarbon group and the alicyclic hydrocarbon group ２ - is -O-, -S-, -CO- or -SO ２ - may be replaced by 2. The resist composition according to claim 1, wherein the alicyclic hydrocarbon group, the aromatic hydrocarbon group and the chain hydrocarbon group each optionally contain a halogen atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a hydroxy group.

5. 2. The resist composition according to claim 1, wherein the structural unit having a group represented by formula (II-x) is a structural unit represented by formula (IIA). 【Chemistry 4】 [In formula (IIA), R ｘ represents an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, a hydrogen atom, or a halogen atom. A Ｘ is a single bond, -A Ｘ１ -* or -CO-O-A Ｘ１ -* (* represents the bonding site with the carbonyl group). A Ｘ１ represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and the —CH ２ - is -O-, -CO- or -N(R ｄ ) - may be replaced. Ring W １ represents a heterocycle having 2 to 36 carbon atoms, a hydrogen atom contained in the heterocycle may be substituted with a halogen atom or a hydrocarbon group having 1 to 24 carbon atoms, and —CH ２ - is -O-, -S-, -CO- or -NR ｃ It may be substituted with a - group. R ｃ and R ｄ each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

6. the resin further comprises a structural unit having an acid labile group, The resist composition according to claim 1, wherein the structural unit having an acid labile group includes 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 5】 [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 have 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 combination thereof, and the alkyl group, alkenyl group, alicyclic hydrocarbon group and aromatic hydrocarbon group may contain a halogen atom. m1 represents an integer of 0 to 14. n1 represents an integer of 0 to 10. n1' represents an integer of 0 to 3. 【Chemistry 6】 [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 7】 [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 8】 [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 a65 - represents *, * represents a bonding site with Ar, R a65 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. X ａ６２ is a single bond, *-O-L ａ６１ - or *-CO-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.]

7. 2. The resist composition according to claim 1, wherein the resin further comprises a structural unit represented by formula (a2-A). 【Chemistry 9】 [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, and when nA2 is 2 or more, the groups in the parentheses may be the same or different. na21 represents an integer of 0 to 4, and when na21 is 2 or more, a plurality of R ａ２７ may be the same or different from each other. mc represents an integer of 0 to 2.

8. Further containing an acid generator, 2. The resist composition according to claim 1, wherein the acid generator comprises a salt represented by formula (B1). 【Chemistry 10】 [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. Z ＋ represents an organic cation.

9. (1) A step of applying the resist composition according to any one of claims 1 to 8 onto a substrate; (2) drying the applied resist composition to form a composition layer; (3) exposing the composition layer to light; (4) heating the composition layer after exposure; and (5) developing the composition layer after heating; A method for producing a resist pattern comprising the steps of:

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