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

Abstract

To provide a salt capable of producing a resist pattern having good CD uniformity, an acid generator and a resist composition containing the acid generator.SOLUTION: There are provided a salt represented by the formula (I), an acid generator and a resist composition. [In the formula, R1 and R2 each represent -O-L1-CO-O-R10; L1 represents an alkanediyl group; R4, R5, R7 and R8 each represent a halogen atom, an alkyl fluoride group or a hydrocarbon group which may have a substituent and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO- or the like; R10 represents a group having a cyclic carbonic acid ester structure; X1 and X2 each represent S or O; m1 represents an integer of 1 to 5, m2 and m8 represent an integer of 0 to 5, m4, m5 and m7 represent an integer of 0 to 4, provided that 1≤m1+m7≤5 and 0≤m2+m8≤5; AI- represents an organic anion.]SELECTED DRAWING: None

Description

Technical Field

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

Background Art

[0002] Patent Document 1 describes a resist composition containing a salt represented by the following formula as an acid generator. TIFF0007716229000001.tif3185Patent Document 2 describes a resist composition containing a salt represented by the following formula as an acid generator. TIFF0007716229000002.tif2687Non-Patent Document 1 describes a salt represented by the following formula. TIFF0007716229000003.tif1185Patent Document 3 describes a salt represented by the following formula. TIFF0007716229000004.tif2389Patent Document 4 describes a salt represented by the following formula. TIFF0007716229000005.tif1156

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Patent Document 2

Patent Document 3

Patent Document 4

Non-Patent Documents

[0004]

Non-Patent Document 1

Summary of the Invention

[0005] An object of the present invention is to provide a salt that forms a resist pattern with better CD uniformity (CDU) than a resist pattern formed from a resist composition containing the above salt. [Means for solving the problem]

[0006] The present invention includes the following inventions. [1] A salt represented by formula (I). TIFF0007716229000006.tif32138 [In formula (I), R 1 and R 2 are each independently -OR 10 , -O-CO-R 10 , -O-CO-OR 10 , -OL 1 -CO-OR 10 Represents. L 1 represents an alkanediyl group having 1 to 6 carbon atoms. R 4 , R 5 , R 7 and R 8 each independently represents a halogen atom, a fluorinated alkyl group having 1 to 6 carbon atoms, or a hydrocarbon group having 1 to 18 carbon atoms, the hydrocarbon group optionally having a substituent, and -CH2- contained in the hydrocarbon group optionally being replaced by -O-, -CO-, -S-, or -SO2-. R 10 represents a group having a cyclic carbonate structure. X 1 and X 2 each independently represents an oxygen atom or a sulfur atom. m1 represents an integer of 1 to 5, and when m1 is 2 or greater, the groups in the parentheses may be the same or different. m2 represents an integer of 0 to 5, and when m2 is 2 or greater, the groups in the parentheses may be the same or different. m4 represents an integer of 0 to 4, and when m4 is 2 or more, a plurality of R 4 may be the same or different from each other. m5 represents an integer of 0 to 4, and when m5 is 2 or more, a plurality of R 5 may be the same or different from each other. m7 represents an integer of 0 to 4, and when m7 is 2 or more, a plurality of R 7 may be the same or different from each other. m8 represents an integer of 0 to 5, and when m8 is 2 or more, a plurality of R 8 may be the same or different from each other. However, 1≦m1+m7≦5, and 0≦m2+m8≦5. AI - represents an organic anion. [2]X 1 and X 2 [1] The salt according to [1], wherein [3]R 10 The salt according to [1] or [2], wherein the group having a cyclic carbonate structure is a group represented by formula (Ix): TIFF0007716229000007.tif3344[In formula (Ix), Ring W x represents a ring of a cyclic carbonate structure which may have a substituent. L 2 represents a single bond or a hydrocarbon group having 1 to 36 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-. * denotes a binding site.] [4] m2 is 0, m8 is 1, and R 8 The salt according to any one of [1] to [3], wherein is a branched alkyl group having 3 or 4 carbon atoms. [5]R 4 or R 5 The salt according to any one of [1] to [4], wherein is an iodine atom, a fluorine atom, or a trifluoromethyl group. [6] R in the benzene ring 4 The bonding position of X1 which is in the ortho or meta position, or the bonding position of R 5 in the benzene ring is ortho or meta to X 2 The salt according to [5]. [7] AI - The salt according to any one of [1] to [6], wherein AI [8] AI - is a sulfonate anion, a sulfonylimide anion, a sulfonylmethide anion or a carboxylate anion. TIFF0007716229000008.tif2555[In formula (I-A), Q 1 and Q 2 each independently represents a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms. L 1 represents a saturated hydrocarbon group having 1 to 24 carbon atoms, wherein -CH2- contained in the saturated hydrocarbon group may be replaced by -O- or -CO-, and a hydrogen atom contained in the saturated hydrocarbon group may be replaced by a fluorine atom or a hydroxy group. Y 1 represents an optionally substituted methyl group or an optionally substituted alicyclic hydrocarbon group having 3 to 24 carbon atoms, wherein -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -SO2- or -CO-.] [9] An acid generator containing the salt according to any one of [1] to [8].

[10] A resist composition containing the acid generator according to [9] and a resin having an acid-labile group.

[11] The resist composition according to

[10] , wherein the resin having an acid-labile group contains at least one selected from the group consisting of a structural unit represented by formula (a1-1) and a structural unit represented by formula (a1-2). TIFF0007716229000009.tif3885[In formula (a1-1) and formula (a1-2), L a1 and L a2each independently represents -O- or *-O-(CH2) k1 -CO-O-, k1 represents an integer from 1 to 7, and * represents a bond to -CO-. 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 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. m1 represents an integer from 0 to 14. n1 represents an integer from 0 to 10. n1’ represents an integer from 0 to 3.]

[12] Further, the resist composition according to

[10] or

[11] , containing a resin containing a structural unit having a fluorine atom.

[13] The resist composition according to any one of

[10] to

[12] , further containing a salt that generates an acid having a lower acidity than the acid generated from the acid generator.

[14] (1) A step of applying the resist composition according to any one of

[10] to

[13] onto a substrate, (2) A step of drying the applied composition to form a composition layer, (3) A step of exposing the composition layer, (4) A step of heating the exposed composition layer, and (5) A step of developing the heated composition layer, a method for manufacturing a resist pattern including these steps.

Advantages of the Invention

[0007] By using the resist composition containing the salt of the present invention, a resist pattern can be manufactured with good CD uniformity (CDU).

Embodiments for Carrying Out the Invention

[0008] In this specification, the term “(meth)acrylic monomer” means “at least one of acrylic monomers and methacrylic monomers”. Expressions such as “(meth)acrylate” and “(meth)acrylic acid” also represent the same meaning. Among the groups described in this specification, those that can take both a linear structure and a branched structure may be either of them. When -CH2- contained in a hydrocarbon group or the like is replaced by -O-, -S-, -CO- or -SO2-, the same examples are applicable to each group. The “combined group” means a group formed by bonding two or more of the exemplified groups, and the valences of these groups may be appropriately changed depending on the bonding form. “Derived from” or “derived” refers to the fact that the polymerizable C═C bond contained in the molecule becomes a -C-C- group by polymerization. When stereoisomers exist, all stereoisomers are included.

[0009] The present invention relates to a salt represented by formula (I) (hereinafter sometimes referred to as “salt (I)”). Among salts (I), the negatively charged side may be referred to as “anion (I)”, and the positively charged side may be referred to as “cation (I)”. TIFF0007716229000010.tif32138[In the formula, all symbols have the same meanings as described above.]

[0010] In formula (I), R 1 and R 2 The alkane diyl group in L 1 include linear alkane diyl 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; and branched alkane diyl 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 and the like. L 1is preferably an alkanediyl group having 1 to 3 carbon atoms, and more preferably a methylene group.

[0011] R 1 and R 2 R included in 10 The cyclic carbonate structure means a structure having —O—CO—O— as atoms constituting the ring. The cyclic carbonate structure may be monocyclic or polycyclic, and may have heteroatoms such as oxygen atoms and nitrogen atoms in addition to the oxygen atoms that form the carbonate structure. The number of carbon atoms in the cyclic carbonate ester structure is preferably 2 to 18, more preferably 3 to 12. The ring of the cyclic carbonate ester structure is preferably a 4-membered ring to 12-membered ring, more preferably a 5-membered ring to 8-membered ring, and even more preferably a 5-membered ring.

[0012] Examples of the cyclic carbonate structure include structures represented by formulas (x1) to (x15), preferably a structure represented by any of formulas (x1) to (x3) and (x9), more preferably a structure represented by any of formulas (x1) to (x2), and even more preferably a structure represented by formula (x1). The bond can be at any position. TIFF0007716229000011.tif88153

[0013] The cyclic carbonate structure may have a substituent, and examples of the substituent include an alkyl group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, a hydroxy group, an alkoxy group having 1 to 6 carbon atoms, and a group formed by combining two or more of these groups. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, etc. The number of carbon atoms in the alkyl group is preferably 1 to 4, and more preferably 1 to 3. The alicyclic hydrocarbon group may be any of a monocyclic, polycyclic, and spirocyclic group, and examples of the alicyclic hydrocarbon group include monocyclic cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, and a cyclododecyl group, and polycyclic cycloalkyl groups such as a norbornyl group and an adamantyl group. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group.

[0014] The group having a cyclic carbonate structure is preferably a group represented by formula (Ix). TIFF0007716229000012.tif3344[In formula (Ix), Ring W x represents a ring of a cyclic carbonate structure which may have a substituent. L 2 represents a single bond or a hydrocarbon group having 1 to 36 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -S-, -CO- or -SO2-. * denotes a binding site.]

[0015] Examples of groups having a cyclic carbonate structure include the following structures: In the following groups, * represents a bond. TIFF0007716229000013.tif101159

[0016] L 2 Examples of the hydrocarbon group having 1 to 36 carbon atoms include aliphatic hydrocarbon groups (chain hydrocarbon groups such as alkanediyl groups, alkenediyl groups, and alkynediyl groups, and monocyclic or polycyclic alicyclic hydrocarbon groups), aromatic hydrocarbon groups, and the like, and may also be hydrocarbon groups formed by combining two or more of these groups. 2 The —CH 2 — contained in the hydrocarbon group in the formula (I) may be replaced by —O—, —S—, —CO— or —SO 2 —.

[0017] Examples of the alkanediyl group include linear alkanediyl groups such as a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, 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; Branched alkanediyl groups such as ethane-1,1-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-2,2-diyl, pentane-2,4-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl groups. The alkanediyl group preferably has 1 to 12 carbon atoms, more preferably 1 to 9 carbon atoms, even more preferably 1 to 6 carbon atoms, and even more preferably 1 to 4 carbon atoms. Examples of the alkenediyl group include an ethenediyl group, a propenediyl group, an isopropenediyl group, a butenediyl group, an isobutenediyl group, a tert-butenediyl group, a pentenediyl group, a hexenediyl group, a heptenediyl group, an octynediyl group, an isooctenediyl group, and a nonenediyl group. Examples of the alkynediyl group include an ethynediyl group, a propynediyl group, an isopropynediyl group, a butynediyl group, an isobutynediyl group, a tert-butynediyl group, a pentynediyl group, a hexynediyl group, an octynediyl group, and a nonynediyl group.

[0018] Examples of the group in which -CH2- in the alkanediyl group is replaced by -O-, -S-, -CO- or -SO2- include a hydroxy group (a group in which -CH2- in the methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- in the ethyl group is replaced by -O-CO-), a thiol group (a group in which -CH2- in the methyl group is replaced by -S-), an alkanediyloxy group (a group in which -CH2- at any position in the alkanediyl group is replaced by -O-), an alkanediyloxycarbonyl group (a group in which -CH2- at any position in the alkanediyl group is replaced by -O-), and Examples of such an alkanediyl group include an alkanediyl group in which -CH- at any position is replaced with -O-CO-, an alkanediylcarbonyl group (an alkanediyl group in which -CH- at any position is replaced with -CO-), an alkanediylcarbonyloxy group (an alkanediyl group in which -CH- at any position is replaced with -CO-O-), an alkanediylthio group (an alkanediyl group in which -CH- at any position is replaced with -S-), and an alkanediylsulfonyl group (an alkanediyl group in which -CH- at any position is replaced with -SO-). Examples of the alkanediyloxy group include alkanediyloxy groups having 1 to 17 carbon atoms, such as a methyleneoxy group, an ethyleneoxy group, a propanediyloxy group, a butanediyloxy group, a pentanediyloxy group, a hexanediyloxy group, an octanediyloxy group, a 2-ethylhexanediyloxy group, a nonanediyloxy group, a decanediyloxy group, and an undecanediyloxy group. Examples of the alkanediyloxycarbonyl group include alkanediyloxycarbonyl groups having 2 to 17 carbon atoms, such as a methyleneoxycarbonyl group, an ethyleneoxycarbonyl group, a propanediyloxycarbonyl group, a butanediyloxycarbonyl group, a pentanediyloxycarbonyl group, a hexanediyloxycarbonyl group, an octanediyloxycarbonyl group, a 2-ethylhexanediyloxycarbonyl group, a nonanediyloxycarbonyl group, a decanediyloxycarbonyl group, and an undecanediyloxycarbonyl group. Examples of the alkanediylcarbonyl group include alkanediylcarbonyl groups having 2 to 18 carbon atoms, such as a methylenecarbonyl group, an ethylenecarbonyl group, a propanediylcarbonyl group, a butanediylcarbonyl group, a pentanediylcarbonyl group, a hexanediylcarbonyl group, an octanediylcarbonyl group, a 2-ethylhexanediylcarbonyl group, a nonanediylcarbonyl group, a decanediylcarbonyl group, and an undecanediylcarbonyl group. Examples of the alkanediylcarbonyloxy group include alkanediylcarbonyloxy groups having 2 to 17 carbon atoms, such as a methylenecarbonyloxy group, an ethylenecarbonyloxy group, a propanediylcarbonyloxy group, a butanediylcarbonyloxy group, a pentanediylcarbonyloxy group, a hexanediylcarbonyloxy group, an octanediylcarbonyloxy group, a 2-ethylhexanediylcarbonyloxy group, a nonanediylcarbonyloxy group, a decanediylcarbonyloxy group, and an undecanediylcarbonyloxy group. Examples of the alkanediylthio group include alkanediylthio groups having 1 to 17 carbon atoms, such as a methylenethio group, an ethylenethio group, a propanediylthio group, a butanediylthio group, a pentanediylthio group, a hexanediylthio group, a heptanediylthio group, an octanediylthio group, a nonanediylthio group, a decanediylthio group, an undecanediylthio group, a dodecanediylthio group, and a 2-methylpropanediylthio group. The alkanediylsulfonyl group includes a sulfonyl group having 1 to 17 carbon atoms, such as a methylenesulfonyl group, an ethylenesulfonyl group, and a propylenesulfonyl group. The substitutions in the alkenediyl group and alkynediyl group may include a carbon-carbon double bond or a carbon-carbon triple bond at any position in the above-mentioned examples of substitutions in the alkanediyl group.

[0019] Examples of the monocyclic 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 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. For example, the following groups, etc. may be mentioned. The bonding site can be at any position. TIFF0007716229000014.tif44168 The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 18, more preferably 3 to 16, and still more preferably 3 to 12. Examples of the group in which -CH2- contained in the alicyclic hydrocarbon group is replaced by -O-, -S-, -CO- or -SO2- include the groups represented below, etc. The bonding site can be at any position. The position of -O- or -CO- in the groups represented below may be replaced by -S- or -SO2- respectively. TIFF0007716229000015.tif47155 Examples of the aromatic hydrocarbon group include phenylene group, naphthylene group, anthrylene group, biphenylene group, phenanthrylene group, etc. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 14, and still more preferably 6 to 10. When -CH2- contained in the hydrocarbon group is replaced by -O-, -S-, -CO- or -SO2-, the number of carbon atoms before replacement is taken as the total number of carbon atoms of the hydrocarbon group. Also, the number may be one or two or more.

[0020] Examples of hydrocarbon groups that combine two or more types include groups that combine an alkanediyl group with an alicyclic hydrocarbon group and / or an aromatic hydrocarbon group, and in these combinations, two or more types of alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may each be combined. Examples include -alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-alicyclic hydrocarbon group-, -alkanediyl group-alicyclic hydrocarbon group-, -alkanediyl group-alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-aromatic hydrocarbon group-, and -aromatic hydrocarbon group-alkanediyl group-. Any of the groups may be bonded to an oxygen atom.

[0021] L 2 Examples of the substituent on the hydrocarbon group include a halogen atom, a cyano group, a hydroxy group, a carboxy group, an alkoxy group having 1 to 12 carbon atoms, an alkoxycarbonyl group having 2 to 13 carbon atoms, an alkylcarbonyl group having 2 to 13 carbon atoms, an alkylcarbonyloxy group having 2 to 13 carbon atoms, an alkoxycarbonyl group having 2 to 13 carbon atoms, an alkylcarbonyl group having 2 to 13 carbon atoms, an alkylcarbonyloxy group having 2 to 13 carbon atoms, and the like. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the alkoxy group having 1 to 12 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, and a dodecyloxy group. The alkoxycarbonyl group having 2 to 13 carbon atoms, the alkylcarbonyl group having 2 to 13 carbon atoms, and the alkylcarbonyloxy group having 2 to 13 carbon atoms represent groups in which a carbonyl group or a carbonyloxy group is bonded to the above-mentioned alkyl group or alkoxy group. Examples of the alkoxycarbonyl group having 2 to 13 carbon atoms include a methoxycarbonyl group, an ethoxycarbonyl group, and a butoxycarbonyl group. Examples of the alkylcarbonyl group having 2 to 13 carbon atoms include an acetyl group, a propionyl group, and a butyryl group. Examples of the alkylcarbonyloxy group having 2 to 13 carbon atoms include an acetyloxy group, a propionyloxy group, and a butyryloxy group. L 2 The hydrocarbon group in may have one or more substituents.

[0022] L 2 is preferably a single bond, an alkanediyl group having 1 to 6 carbon atoms (-CH2- contained in the alkanediyl group may be replaced with -O- or -CO-), an alicyclic hydrocarbon group having 3 to 18 carbon atoms (-CH2- contained in the alicyclic hydrocarbon group may be replaced with -O- or -CO-), or a group combining an alkanediyl group having 1 to 6 carbon atoms with an alicyclic hydrocarbon group having 3 to 18 carbon atoms (-CH2- contained in the alkanediyl group and the alicyclic hydrocarbon group may be replaced with -O- or -CO-), more preferably an alkanediyl group having 1 to 6 carbon atoms, even more preferably an alkanediyl group having 1 to 3 carbon atoms, and even more preferably a methylene group. R 1 and R 2 is -O-CO-R 10 , -O-CO-OR 10 , -OL 1 -CO-OR 10 is preferably —O—CO—OR 10 , -OL 1 -CO-OR 10 It is more preferable that: R 1 and R 2 The bond positions of X 1 and X 2 The bonding position of X may be either o-position, m-position or p-position. 1 and X 2 It is preferable that the bond is at the p-position relative to the bonding position of

[0023] R 4 , R 5 , R 7 and R 8 Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R 4 , R 5 , R 7 and R 8 The fluorinated alkyl group having 1 to 12 carbon atoms refers to an alkyl group having 1 to 12 carbon atoms and containing a fluorine atom, and examples thereof include perfluoroalkyl groups having 1 to 12 carbon atoms (trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, nonafluorobutyl group), as well as 2,2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group, 4,4,4-trifluorobutyl group, and 3,3,4,4,4-pentafluorobutyl group. The number of carbon atoms in the fluorinated alkyl group is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3. R 4 , R 5 , R 7 and R 8 Examples of the hydrocarbon group having 1 to 18 carbon atoms include chain hydrocarbon groups such as alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and groups formed by combining these groups. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, a 2-ethylhexyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, and a dodecyl group. The number of carbon atoms in the alkyl group is preferably 1 to 12, more preferably 1 to 9, even more preferably 1 to 6, and still more preferably 1 to 4. The alicyclic hydrocarbon group may be monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclodecyl group and the like. Examples of the polycyclic alicyclic hydrocarbon group include decahydronaphthyl group, adamantyl group, norbornyl group and the like. 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. Specifically, examples of the alicyclic hydrocarbon group include the same groups as those exemplified by L 2 above. Examples of the aromatic hydrocarbon group include phenyl group, naphthyl group, biphenyl group, anthryl group, phenanthryl group, binaphthyl group and the like. 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. Examples of the group formed by combination include a group formed by combining an aromatic hydrocarbon group and a chain hydrocarbon group (for example, aromatic hydrocarbon group - alkane diyl group - *, alkyl group - aromatic hydrocarbon group - *), a group formed by combining an alicyclic hydrocarbon group and a chain hydrocarbon group (for example, alicyclic hydrocarbon group - alkane diyl group - *, alkyl group - alicyclic hydrocarbon group - *), and a group formed by combining an aromatic hydrocarbon group and an alicyclic hydrocarbon group (for example, aromatic hydrocarbon group - alicyclic hydrocarbon group - *, alicyclic hydrocarbon group - aromatic hydrocarbon group - *). * represents a bonding site. Examples of the aromatic hydrocarbon group - alkane diyl group - * include aralkyl groups such as benzyl group and phenethyl group. Examples of the alkyl group - aromatic hydrocarbon group - * include tolyl group, xylyl group, cumenyl group and the like. Examples of the alicyclic hydrocarbon group - alkane diyl group - * include cycloalkylalkyl groups such as cyclohexylmethyl group, cyclohexylethyl group, 1-(adamantan-1-yl)methyl group, 1-(adamantan-1-yl)-1-methylethyl and the like. 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. 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. In addition, two or more types of alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups may be combined. Furthermore, -CH2- contained in the alicyclic hydrocarbon group or chain hydrocarbon group (alkanediyl group, alkyl group) may be replaced with -O-, -S-, -CO-, or -SO2-. Any of the groups in the combined group may be bonded to the benzene ring. Examples of groups in which -CH2- in a hydrocarbon group is replaced by -O-, -CO-, -S-, or -SO2- include a hydroxy group (a group in which -CH2- in a methyl group is replaced by -O-), a carboxy group (a group in which -CH2-CH2- in an ethyl group is replaced by -O-CO-), a thiol group (a group in which -CH2- in a methyl group is replaced by -S-), an alkoxy group (a group in which -CH2- at any position in an alkyl group is replaced by -O-), an alkoxycarbonyl group (a group in which -CH2-CH2- at any position in an alkyl group is replaced by -O-CO-), and an alkylcarbonyl group. Examples of such groups include (a group in which -CH2- at any position in an alkyl group is replaced with -CO-), alkylcarbonyloxy groups (a group in which -CH2-CH2- at any position in an alkyl group is replaced with -CO-O-), alkylthio groups (a group in which -CH2- at any position in an alkyl group is replaced with -S-), alkylsulfonyl groups (a group in which -CH2- at any position in an alkyl group is replaced with -SO2-), cycloalkoxy groups, cycloalkylalkoxy groups, alkoxycarbonyloxy groups, aromatic hydrocarbon group-carbonyloxy groups, and groups in which two or more of these groups are combined. Examples of the alkoxy group include alkoxy groups having 1 to 17 carbon atoms, such as a methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, undecyloxy group, etc. The number of carbon atoms in the alkoxy group is preferably 1 to 11, more preferably 1 to 6, and even more preferably 1 to 4. The alkoxycarbonyl group, alkylcarbonyl group and alkylcarbonyloxy group represent groups in which a carbonyl group or carbonyloxy group is bonded to the above-mentioned alkyl group or alkoxy group. Examples of the alkoxycarbonyl group include alkoxycarbonyl groups having 2 to 17 carbon atoms, such as a methoxycarbonyl group, an ethoxycarbonyl group, and a butoxycarbonyl group. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 18 carbon atoms, such as an acetyl group, a propionyl group, and a butyryl group. Examples of the alkylcarbonyloxy group include alkylcarbonyloxy groups having 2 to 17 carbon atoms, such as an acetyloxy group, a propionyloxy group, and a butyryloxy group. The number of carbon atoms in the alkoxycarbonyl group is preferably 2 to 11, more preferably 2 to 6, and even more preferably 2 to 4. The number of carbon atoms in the alkylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, and even more preferably 2 to 4. The number of carbon atoms in the alkylcarbonyloxy group is preferably 2 to 11, more preferably 2 to 6, and even more preferably 2 to 4. The alkylthio group includes alkylthio groups having 1 to 12 carbon atoms, such as a methylthio group, an ethylthio group, a propylthio group, a butylthio group, etc. The alkylthio group preferably has 1 to 6 carbon atoms, and more preferably has 1 to 4 carbon atoms. Examples of the alkylsulfonyl group include alkylsulfonyl groups having 1 to 12 carbon atoms, such as a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, etc. The number of carbon atoms in the alkylsulfonyl group is preferably 1 to 11, more preferably 1 to 6, and even more preferably 1 to 4. Examples of cycloalkoxy groups include cycloalkoxy groups having 3 to 17 carbon atoms, such as a cyclohexyloxy group. Examples of cycloalkylalkoxy groups include cycloalkylalkoxy groups having 4 to 17 carbon atoms, such as a cyclohexylmethoxy group. Examples of alkoxycarbonyloxy groups include alkoxycarbonyloxy groups having 2 to 16 carbon atoms, such as a butoxycarbonyloxy group. Examples of aromatic hydrocarbon group-carbonyloxy groups include aromatic hydrocarbon group-carbonyloxy groups having 7 to 17 carbon atoms, such as a benzoyloxy group. Furthermore, examples of groups in which -CH2- contained in an alicyclic hydrocarbon group is replaced by -O- or -CO- include L 2 Examples of the groups include the same groups as those exemplified in the above. When a -CH2- in a hydrocarbon group is replaced with -O- or -CO-, the number of carbon atoms before the replacement is the total number of carbon atoms in the hydrocarbon group. In addition, the number may be 1 or 2 or more. R 4 , R 5 , R 7 and R 8 Examples of the substituent that the hydrocarbon group may have include a halogen atom, a cyano group, and an alkyl group having 1 to 12 carbon atoms (-CH2- contained in the alkyl group may be replaced with -O- or -CO-). Examples of the halogen atom include the same groups as those mentioned above. Examples of the alkyl group having 1 to 12 carbon atoms include the same groups as those mentioned above. When -CH2- in an alkyl group is replaced with -O- or -CO- as a substituent, the number of carbon atoms before the replacement is counted as the total number of carbon atoms in the alkyl group. Examples of the substituted group include a hydroxy group, a carboxy group, an alkoxy group, an alkoxycarbonyl group, an alkylcarbonyl group, and an alkylcarbonyloxy group. Examples of the alkoxy group, alkoxycarbonyl group, alkylcarbonyl group and alkylcarbonyloxy group include the same groups as those described above. The hydrocarbon group may have one substituent or a plurality of substituents.

[0024] X 1 is preferably an oxygen atom. X 2 is preferably an oxygen atom. X 1 and X 2 may be bonded to the ortho position, meta position, or para position with respect to the bonding position of I + Among them, it is preferably bonded to the meta position or para position with respect to the bonding position of I + and more preferably bonded to the para position. m1 is preferably 1 or 2, and more preferably 1. m2 is preferably 0, 1, or 2. m4 is preferably 0, 1, 2, or 4, and more preferably 0, 1, or 2. m5 is preferably 0, 1, 2, or 4, and more preferably 0, 1, or 2. m7 is preferably 0, 1, or 2, and more preferably 0 or 1. m8 is preferably 0 or 1. R 4 and R 5 are each independently preferably a halogen atom, a C1-C4 fluoroalkyl group, or a C1-C6 alkyl group (wherein -CH2- contained in the alkyl group may be replaced by -O- or -CO-), more preferably a halogen atom, a C1-C4 fluoroalkyl group, or a C1-C4 alkyl group (wherein -CH2- contained in the alkyl group may be replaced by -O- or -CO-), and even more preferably a fluorine atom, an iodine atom, a trifluoromethyl group, or a C1-C4 alkyl group. R 7 and R 8are each independently preferably a halogen atom, a fluorinated alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 6 carbon atoms (wherein —CH— contained in the alkyl group may be replaced with —O— or —CO—), more preferably a halogen atom, a fluorinated alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms (wherein —CH— contained in the alkyl group may be replaced with —O— or —CO—), still more preferably a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms (wherein —CH— contained in the alkyl group may be replaced with —O— or —CO—), and even more preferably a fluorine atom, an iodine atom, a trifluoromethyl group, a methyl group, a t-butyl group, a hydroxy group, or a methoxy group. When m2 is 0, m8 is 1, and R 8 is preferably a branched alkyl group having 3 or 4 carbon atoms. When m4 is 2, R 1 The bond position of is X 1 Preferably, the bond between the two R 4 One of them is X 1 It is preferable that one is the m-position relative to the bonding position (1-position) of and the other is the o-position, and it is preferable that one is the 3-position and the other is the 6-position. When m5 is 2, R 2 The bond position of is X 2 Preferably, the bond between the two R 5 One of them is X 2 It is preferable that one is the m-position relative to the bonding position (1-position) of and the other is the o-position, and it is preferable that one is the 3-position and the other is the 6-position.

[0025] Examples of the cation of the salt (I) include cations represented by the following formulae (Ic-1) to (Ic-40). TIFF0007716229000016.tif193157

[0026] TIFF0007716229000017.tif194167

[0027] TIFF0007716229000018.tif146162

[0028] TIFF0007716229000019.tif98152

[0029] TIFF0007716229000020.tif229165

[0030] TIFF0007716229000021.tif97122

[0031] AI - Examples of the organic anion represented by the formula AI include a sulfonate anion, a sulfonylimide anion, a sulfonylmethide anion, and a carboxylate anion. - The organic anion represented by formula (IA) is preferably a sulfonate anion, and more preferably an anion represented by formula (IA). TIFF0007716229000022.tif2965[In formula (IA), Q 1 and Q 2 each independently represents a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms. L 1 represents a saturated hydrocarbon group having 1 to 24 carbon atoms, wherein -CH2- contained in the saturated hydrocarbon group may be replaced by -O- or -CO-, and wherein a hydrogen atom contained in the saturated hydrocarbon group may be substituted by a fluorine atom or a hydroxy group. Y 1 represents an optionally substituted methyl group or an optionally substituted alicyclic hydrocarbon group having 3 to 24 carbon atoms, and -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -SO2- or -CO-.]

[0032] In formula (IA), when -CH2- in the saturated hydrocarbon group is replaced with -O- or -C(=O)-, the number of carbon atoms before the replacement is the number of carbon atoms in the saturated hydrocarbon group. Also, when -CH2- in the alicyclic hydrocarbon group is replaced with -O-, -SO2-, or -C(=O)-, the number of carbon atoms before the replacement is the number of carbon atoms in the alicyclic hydrocarbon group.

[0033] Q 1 and Q 2 Examples of the perfluoroalkyl group having 1 to 6 carbon atoms include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group, and a perfluorohexyl group. Q 1 and Q 2 and are each independently preferably a fluorine atom or a trifluoromethyl group, and more preferably both are fluorine atoms.

[0034] L 1 Examples of the divalent saturated hydrocarbon group in include a linear alkanediyl group, a branched alkanediyl group, and a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, and may also be a group formed by combining two or more of these groups. Specific examples include linear alkanediyl groups such as a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, a heptane-1,7-diyl group, an octane-1,8-diyl group, a nonane-1,9-diyl group, a decane-1,10-diyl group, an undecane-1,11-diyl group, a dodecane-1,12-diyl group, a tridecane-1,13-diyl group, a tetradecane-1,14-diyl group, a pentadecane-1,15-diyl group, a hexadecane-1,16-diyl group, and a heptadecane-1,17-diyl group; 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; 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; Examples include polycyclic divalent alicyclic saturated hydrocarbon groups such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, etc. L 1 Examples of the group in which -CH2- contained in the divalent saturated hydrocarbon group represented by is replaced by -O- or -CO- include groups represented by any of formula (b1-1) to formula (b1-3). In the groups represented by formula (b1-1) to formula (b1-3) and the groups represented by formula (b1-4) to formula (b1-11) which are specific examples thereof, * and ** represent bonding sites, and * represents the bonding site with -Y 1 represents the bonding site with.

[0035] TIFF0007716229000023.tif26118[In formula (b1-1), L b2 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms. L b3 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms or hydroxy groups, and -CH2- contained in the saturated hydrocarbon group may be replaced by -O- or -CO-. However, the total number of carbon atoms of L b2 and L b3 is 22 or less. In formula (b1-2), Lb4 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom. L b5 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group, and -CH2- contained in the saturated hydrocarbon group may be substituted with -O- or -CO-. However, L b4 and L b5 The total number of carbon atoms is 22 or less. In formula (b1-3), L b6 represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group. L b7 represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group, and -CH2- contained in the saturated hydrocarbon group may be substituted with -O- or -CO-. However, L b6 and L b7 The total number of carbon atoms is 23 or less.

[0036] In the groups represented by formulae (b1-1) to (b1-3), when -CH2- contained in the saturated hydrocarbon group is replaced with -O- or -CO-, the number of carbon atoms before replacement is defined as the number of carbon atoms of the saturated hydrocarbon group. As the divalent saturated hydrocarbon group, L b1 Examples of the divalent saturated hydrocarbon group include the same as the divalent saturated hydrocarbon group. L b2 is preferably a single bond. L b3 is preferably a divalent saturated hydrocarbon group having 1 to 4 carbon atoms. L b4 is preferably a divalent saturated hydrocarbon group having 1 to 8 carbon atoms, and a hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted with a fluorine atom. L b5 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b6 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 4 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom. L b7 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group, and -CH2- contained in the divalent saturated hydrocarbon group may be replaced with -O- or -CO-. L 1 As the group in which -CH2- contained in the divalent saturated hydrocarbon group represented by 1 is replaced with -O- or -CO-, a group represented by formula (b1-1) or formula (b1-3) is preferable.

[0037] Examples of the group represented by formula (b1-1) include groups represented by formula (b1-4) to formula (b1-8), respectively. TIFF0007716229000024.tif48120[In formula (b1-4), L b8 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group. In formula (b1-5), L b9 represents a divalent saturated hydrocarbon group having 1 to 20 carbon atoms, and -CH2- contained in the divalent saturated hydrocarbon group may be replaced with -O- or -CO-. L b10 represents a single bond or a divalent saturated hydrocarbon group having 1 to 19 carbon atoms, and a hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group. However, the total number of carbon atoms of L b9 and L b10 is 20 or less. In formula (b1-6), L b11 represents a divalent saturated hydrocarbon group having 1 to 21 carbon atoms. L b12 represents a single bond or a divalent saturated hydrocarbon group having 1 to 20 carbon atoms, and a hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group. However, L b11 and L b12 The total number of carbon atoms is 21 or less. In formula (b1-7), L b13 represents a divalent saturated hydrocarbon group having 1 to 19 carbon atoms. L b14 represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the divalent saturated hydrocarbon group may be replaced with -O- or -CO-. L b15 represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and a hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group. However, L b13 ~L b15 The total number of carbon atoms is 19 or less. In formula (b1-8), L b16 represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the divalent saturated hydrocarbon group may be replaced with -O- or -CO-. L b17 represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms. L b18 represents a single bond or a divalent saturated hydrocarbon group having 1 to 17 carbon atoms, and a hydrogen atom contained in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group. However, L b16 ~L b18 The total number of carbon atoms is 19 or less. L b8 is preferably a divalent saturated hydrocarbon group having 1 to 4 carbon atoms. L b9 is preferably a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b10is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 19 carbon atoms, and more preferably a single bond or a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b11 is preferably a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b12 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b13 is preferably a divalent saturated hydrocarbon group having 1 to 12 carbon atoms. L b14 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 6 carbon atoms. L b15 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and more preferably a single bond or a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b16 is preferably a divalent saturated hydrocarbon group having 1 to 12 carbon atoms. L b17 is preferably a divalent saturated hydrocarbon group having 1 to 6 carbon atoms. L b18 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 17 carbon atoms, and more preferably a single bond or a divalent saturated hydrocarbon group having 1 to 4 carbon atoms.

[0038] Examples of the group represented by formula (b1-3) include groups represented by formulas (b1-9) to (b1-11). TIFF0007716229000025.tif23139 [In formula (b1-9), L b19 represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom. L b20represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms, hydroxy groups or alkylcarbonyloxy groups. The -CH2- contained in the alkylcarbonyloxy group may be replaced with -O- or -CO-, and the hydrogen atoms contained in the alkylcarbonyloxy group may be substituted with hydroxy groups. However, L b19 and L b20 have a total carbon number of 23 or less. In formula (b1-10), L b21 represents a single bond or a divalent saturated hydrocarbon group having 1 to 21 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms. L b22 represents a single bond or a divalent saturated hydrocarbon group having 1 to 21 carbon atoms. L b23 represents a single bond or a divalent saturated hydrocarbon group having 1 to 21 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms, hydroxy groups or alkylcarbonyloxy groups. The -CH2- contained in the alkylcarbonyloxy group may be replaced with -O- or -CO-, and the hydrogen atoms contained in the alkylcarbonyloxy group may be substituted with hydroxy groups. However, L b21 L b22 and L b23 have a total carbon number of 21 or less. In formula (b1-11), L b24 represents a single bond or a divalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms. L b25 represents a divalent saturated hydrocarbon group having 1 to 21 carbon atoms. L b26represents a single bond or a divalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms, hydroxy groups or alkylcarbonyloxy groups. -CH2- contained in the alkylcarbonyloxy group may be replaced with -O- or -CO-, and the hydrogen atoms contained in the alkylcarbonyloxy group may be substituted with hydroxy groups. However, L b24 , L b25 and L b26 have a total carbon number of 21 or less. In addition, in the group represented by the formula (b1-9) to the group represented by the formula (b1-11), when the hydrogen atoms contained in the saturated hydrocarbon group are substituted with alkylcarbonyloxy groups, the carbon number before substitution is defined as the carbon number of the saturated hydrocarbon group. Examples of the alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, a butyryloxy group, a cyclohexylcarbonyloxy group, an adamantylcarbonyloxy group, and the like.

[0039] Examples of the group represented by the formula (b1-4) include the following. TIFF0007716229000026.tif16153

[0040] Examples of the group represented by the formula (b1-5) include the following. TIFF0007716229000027.tif64153

[0041] Examples of the group represented by the formula (b1-6) include the following. TIFF0007716229000028.tif44148

[0042] Examples of the group represented by the formula (b1-7) include the following. TIFF0007716229000029.tif63153

[0043] Examples of the group represented by the formula (b1-8) include the following. TIFF0007716229000030.tif23150

[0044] Examples of the group represented by formula (b1-2) include the following. TIFF0007716229000031.tif31161

[0045] Examples of the group represented by formula (b1-9) include the following. TIFF0007716229000032.tif44137

[0046] Examples of the group represented by formula (b1-10) include the following. TIFF0007716229000033.tif92165

[0047] Examples of the group represented by formula (b1-11) include the following. TIFF0007716229000034.tif84164

[0048] Y 1 Examples of the alicyclic hydrocarbon group represented by 1 include the groups represented by formula (Y1) to formula (Y11), formula (Y36) to formula (Y38). Y 1 When -CH2- contained in the alicyclic hydrocarbon group represented by 1 is replaced by -O-, -SO2- or -CO-, the number thereof may be one or two or more. Examples of such groups include the groups represented by formula (Y12) to formula (Y35), formula (Y39) to formula (Y43). * represents the bonding site with L 1 represents the bonding site with TIFF0007716229000035.tif85168

[0049] Y 1The alicyclic hydrocarbon group represented by the formula (Y1) is preferably a group represented by any one of formulas (Y1) to (Y20), formula (Y26), formula (Y27), formula (Y30), formula (Y31), formula (Y39) to formula (Y43), more preferably a group represented by formula (Y11), formula (Y15), formula (Y16), formula (Y20), formula (Y26), formula (Y27), formula (Y30), formula (Y31), formula (Y39), formula (Y40), formula (Y42) or formula (Y43), and even more preferably a group represented by formula (Y11), formula (Y15), formula (Y20), formula (Y26), formula (Y27), formula (Y30), formula (Y31), formula (Y39), formula (Y40), formula (Y42) or formula (Y43). Y 1 is a spiro ring having an oxygen atom, such as those of formula (Y28) to formula (Y35), formula (Y39), formula (Y40), formula (Y42) or formula (Y43), the alkanediyl group between the two oxygen atoms preferably has one or more fluorine atoms. Furthermore, among the alkanediyl groups contained in the ketal structure, it is preferred that the methylene group adjacent to the oxygen atom is not substituted with a fluorine atom.

[0050] Y 1 The substituent of the methyl group represented by the formula (I) is a halogen atom, a hydroxy group, an alicyclic hydrocarbon group having 3 to 16 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, a glycidyloxy group, -(CH2) ja -CO-OR b1 group or -(CH2) ja -O-CO-R b1 group (in the formula, R b1 represents an alkyl group having 1 to 16 carbon atoms, an alicyclic hydrocarbon group having 3 to 16 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a combination thereof. ja represents an integer of 0 to 4. -CH2- contained in the alkyl group and the alicyclic hydrocarbon group may be replaced by -O-, -SO2-, or -CO-, and a hydrogen atom contained in the alkyl group, the alicyclic hydrocarbon group, and the aromatic hydrocarbon group may be replaced by a hydroxy group or a fluorine atom. Y 1Examples of the substituent of the alicyclic hydrocarbon group represented by include a halogen atom, a hydroxy group, an alkyl group having 1 to 16 carbon atoms which may be substituted with a hydroxy group (wherein -CH2- contained in the alkyl group may be replaced by -O- or -CO-), an alicyclic hydrocarbon group having 3 to 16 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, an aralkyl group having 7 to 21 carbon atoms, a glycidyloxy group, -(CH2) ja -CO-O-R b1 group or -(CH2) ja -O-CO-R b1 group (wherein R b1 represents an alkyl group having 1 to 16 carbon atoms, an alicyclic hydrocarbon group having 3 to 16 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms or a group combining these. ja represents any integer from 0 to 4. -CH2- contained in the alkyl group and the alicyclic hydrocarbon group may be replaced by -O-, -SO2- or -CO-, and a hydrogen atom contained in the alkyl group, the alicyclic hydrocarbon group and the aromatic hydrocarbon group may be replaced by a hydroxy group or a fluorine atom.).

[0051] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. Examples of the alicyclic hydrocarbon group include a cyclopentyl group, a cyclohexyl group, a methylcyclohexyl group, a dimethylcyclohexyl group, a cycloheptyl group, a cyclooctyl group, a norbornyl group, an adamantyl group and the like. The alicyclic hydrocarbon group may have a chain hydrocarbon group, and examples thereof include a methylcyclohexyl group and a dimethylcyclohexyl group. The number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 12, more preferably 3 to 10. Examples of the aromatic hydrocarbon group include aryl groups such as phenyl group, naphthyl group, anthryl group, biphenyl group, phenanthryl group, etc. The aromatic hydrocarbon group may have a chain hydrocarbon group or an alicyclic hydrocarbon group, and examples of the aromatic hydrocarbon group having a chain hydrocarbon group with 1 to 18 carbon atoms include (tolyl group, xylyl group, cumenyl group, mesityl group, p-methylphenyl group, p-ethylphenyl group, p-tert-butylphenyl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group, etc.), and examples of the aromatic hydrocarbon group having an alicyclic hydrocarbon group with 3 to 18 carbon atoms include (p-cyclohexylphenyl group, p-adamantylphenyl group, etc.). The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 14, more preferably 6 to 10. Examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, 2-ethylhexyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, etc. The number of carbon atoms of the alkyl group is preferably 1 to 12, more preferably 1 to 6, and even more preferably 1 to 4. Examples of the alkyl group substituted with a hydroxy group include hydroxyalkyl groups such as hydroxymethyl group and hydroxyethyl group. Examples of the aralkyl group include benzyl group, phenethyl group, phenylpropyl group, naphthylmethyl group, naphthylethyl group, etc. Examples of the group in which -CH2- contained in the alkyl group is replaced by -O-, -SO2- or -CO- etc. include alkoxy group, alkoxycarbonyl group, alkylcarbonyl group, alkylsulfonyl group, alkylcarbonyloxy group or a group combining these. Examples of the alkoxy group include methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, decyloxy group, dodecyloxy group, etc. The number of carbon atoms of the alkoxy group is preferably 1 to 12, more preferably 1 to 6, and even more preferably 1 to 4. Examples of the alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a butoxycarbonyl group and the like. The number of carbon atoms of the alkoxycarbonyl group is preferably 2 to 12, more preferably 2 to 6, and still more preferably 2 to 4. Examples of the alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group and the like. The number of carbon atoms of the alkylsulfonyl group is preferably 1 to 12, more preferably 1 to 6, and still more preferably 1 to 4. Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, a butyryl group and the like. The number of carbon atoms of the alkylcarbonyl group is preferably 2 to 12, more preferably 2 to 6, and still more preferably 2 to 4. Examples of the alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, a butyryloxy group and the like. The number of carbon atoms of the alkylcarbonyloxy group is preferably 2 to 12, more preferably 2 to 6, and still more preferably 2 to 4. Examples of the combined group include a group formed by combining an alkoxy group and an alkyl group, a group formed by combining an alkoxy group and an alkoxy group, a group formed by combining an alkoxy group and an alkylcarbonyl group, a group formed by combining an alkoxy group and an alkylcarbonyloxy group, and the like. Examples of the group formed by combining an alkoxy group and an alkyl group include alkoxyalkyl groups such as a methoxymethyl group, a methoxyethyl group, an ethoxyethyl group, an ethoxymethyl group and the like. The number of carbon atoms of the alkoxyalkyl group is preferably 2 to 12, more preferably 2 to 6, and still more preferably 2 to 4. Examples of the group formed by combining an alkoxy group and an alkoxy group include alkoxyalkoxy groups such as a methoxymethoxy group, a methoxyethoxy group, an ethoxymethoxy group, an ethoxyethoxy group and the like. The number of carbon atoms of the alkoxyalkoxy group is preferably 2 to 12, more preferably 2 to 6, and still more preferably 2 to 4. Examples of the group combining an alkoxy group and an alkylcarbonyl group include alkoxyalkylcarbonyl groups such as a methoxyacetyl group, a methoxypropionyl group, an ethoxyacetyl group, an ethoxypropionyl group, etc. The number of carbon atoms in the alkoxyalkylcarbonyl group is preferably 3 to 13, more preferably 3 to 7, and even more preferably 3 to 5. Examples of the group combining an alkoxy group and an alkylcarbonyloxy group include alkoxyalkylcarbonyloxy groups such as a methoxyacetyloxy group, a methoxypropionyloxy group, an ethoxyacetyloxy group, an ethoxypropionyloxy group, etc. The number of carbon atoms in the alkoxyalkylcarbonyloxy group is preferably 3 to 13, more preferably 3 to 7, and even more preferably 3 to 5. Examples of the group in which -CH2- in the alicyclic hydrocarbon group is replaced by -O-, -SO2-, -CO- or the like include groups represented by formulae (Y12) to (Y35) and formulae (Y39) to (Y43).

[0052] Y 1 Examples include the following: TIFF0007716229000036.tif160165

[0053] Y 1 is preferably an alicyclic hydrocarbon group of 3 to 24 carbon atoms which may have a substituent, more preferably an alicyclic hydrocarbon group of 3 to 20 carbon atoms which may have a substituent, even more preferably an alicyclic hydrocarbon group of 3 to 18 carbon atoms which may have a substituent, even more preferably an alicyclic hydrocarbon group substituted with a hydroxy group, and even more preferably an adamantyl group which may have a substituent, and -CH2- constituting the alicyclic hydrocarbon group or the adamantyl group may be replaced with -CO-, -SO2- or -CO-. 1is specifically preferably an adamantyl group, a hydroxyadamantyl group, an oxoadamantyl group, or a group represented by formula (Y42) or formula (Y100) to formula (Y114), and particularly preferably a hydroxyadamantyl group, an oxoadamantyl group, a group containing these, or a group represented by formula (Y42) or formula (Y100) to formula (Y114).

[0054] The anion represented by formula (IA) is preferably an anion represented by formula (IA-1) to formula (IA-59) (hereinafter, sometimes referred to as "anion (IA-1)" or the like depending on the formula number), and more preferably an anion represented by any of formulas (IA-1) to (IA-4), (IA-9), (IA-10), (IA-24) to (IA-33), (IA-36) to (IA-40), and (IA-47) to (IA-59). TIFF0007716229000037.tif72141

[0055] TIFF0007716229000038.tif77163

[0056] TIFF0007716229000039.tif54160

[0057] TIFF0007716229000040.tif195150

[0058] TIFF0007716229000041.tif170160

[0059] where R i2 ~R i7 are each independently, for example, an alkyl group having 1 to 4 carbon atoms, preferably a methyl group or an ethyl group. i8 is, for example, a chain hydrocarbon group having 1 to 12 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 5 to 12 carbon atoms, or a group formed by combining these, more preferably a methyl group, an ethyl group, a cyclohexyl group, or an adamantyl group. A41 Q is a single bond or an alkanediyl group having 1 to 4 carbon atoms.1 and Q 2 represents the same meaning as described above. Specific examples of the anion represented by formula (I-A) include the anions described in JP-A-2010-204646.

[0060] Preferred examples of the anion represented by formula (I-A) include the anions represented by formula (I-a-1) to formula (I-a-38), respectively. TIFF0007716229000042.tif184157

[0061] TIFF0007716229000043.tif215167

[0062] Among them, an anion represented by any of formula (I-a-1) to formula (I-a-3), formula (I-a-7) to formula (I-a-19), and formula (I-a-22) to formula (I-a-38) is preferred.

[0063] AI - Examples of the sulfonylimide anion represented by include the following. TIFF0007716229000044.tif36136

[0064] Examples of the sulfonylmethide anion include the following. TIFF0007716229000045.tif30128

[0065] Examples of the carboxylic acid anion include the following. TIFF0007716229000046.tif42154

[0066] Specific examples of salt (I) include salts obtained by arbitrarily combining the above-mentioned cations and anions. Specific examples of salt (I) are shown in the following table. In the table below, each symbol represents the symbol attached to the structure representing the above-mentioned anion or cation, and "~" indicates that the salt (I) corresponds to the anion (I). For example, salt (I-1) is a salt consisting of an anion represented by formula (Ia-1) and a cation represented by formula (Ic-1), salt (I-2) is a salt consisting of an anion represented by formula (Ia-2) and a cation represented by formula (Ic-1), and salt (I-39) is a salt consisting of an anion represented by formula (Ia-1) and a cation represented by formula (Ic-2). TIFF0007716229000047.tif27144 [Table 1]

[0067] Among them, the salt (I) is preferably a salt formed by combining an anion represented by any one of the formulas (I-a-1) to (I-a-4), (I-a-7) to (I-a-11), (I-a-14) to (I-a-30), and (I-a-35) to (I-a-38) with a cation represented by any one of the formulas (I-c-1) to (I-c-40). Specifically, salts (I-1) to (I-4), salts (I-7) to (I-11), salts (I-14) to (I-30), salts (I-35) to (I-38), salts (I-39) to (I-42), salts (I-45) to (I-49), salts (I-52) to (I-68), salts (I-73) to (I-76), salts (I-77) to (I-80), salts (I-83) to (I-87), salts (I-90) to (I-106), salts (I-111) to (I-114), salts (I-115) to (I-118), salts (I-121) to (I-125), salts (I-128) to (I-144), salts (I-149) to (I-152), salts (I-153) to (I-156), salts (I-159) to (I-163), salts (I-166) to (I-182), salts (I-187) to (I-190), salts (I-191) to (I-194), salts (I-197) to (I-201), salts (I-204) to (I-220), salts (I-225) to (I-228), salts (I-229) to (I-232), salts (I-235) to (I-239), salts (I-242) to (I-258), salts (I-263) to (I-266), salts (I-267) to (I-270), salts (I-273) to (I-277), salts (I-280) to (I-296), salts (I-301) to (I-304), salts (I-305) to (I-308), salts (I-311) to (I-315), salts (I-318) to (I-334), salts (I-339) to (I-342), salts (I-343) to (I-346), salts (I-349) to (I-353), salts (I-356) to (I-372), salts (I-377) to (I-380), salts (I-381) to (I-384), salts (I-387) to (I-391), salts (I-394) to (I-410), salts (I-415) to (I-418), salts (I-419) to (I-422), salts (I-425) to (I-429), salts (I-432) to (I-448), salts (I-453) to (I-456).Salt (I-457) ~ Salt (I-460), Salt (I-463) ~ Salt (I-467), Salt (I-470) ~ Salt (I-486), Salt (I-491) ~ Salt (I-494), Salt (I-495) ~ Salt (I-498), Salt (I-501) ~ Salt (I-505), Salt (I-508) ~ Salt (I-52 4), Salt (I-529) ~ Salt (I-532), Salt (I-533) ~ Salt (I-536), Salt (I-539) ~ Salt (I-543), Salt (I-546) ~ Salt (I-562), Salt (I-567) ~ Salt (I-570), Salt (I-571) ~ Salt (I-574), Salt (I-577) ~ Salt (I- 581), Salt (I-584) ~ Salt (I-600), Salt (I-605) ~ Salt (I-608), Salt (I-609) ~ Salt (I-612), Salt (I-615) ~ Salt (I-619), Salt (I-622) ~ Salt (I-638), Salt (I-643) ~ Salt (I-646), Salt (I-647) ~ Salt ( I-650), Salt (I-653) ~ Salt (I-657), Salt (I-660) ~ Salt (I-676), Salt (I-681) ~ Salt (I-684), Salt (I-685) ~ Salt (I-688), Salt (I-691) ~ Salt (I-695), Salt (I-698) ~ Salt (I-714), Salt (I-719) ~ Salt (I-722), Salt (I-723) ~ Salt (I-726), Salt (I-729) ~ Salt (I-733), Salt (I-736) ~ Salt (I-752), Salt (I-757) ~ Salt (I-760), Salt (I-761) ~ Salt (I-764), Salt (I-767) ~ Salt (I-771), Salt (I-77 4) ~ Salt (I-790), Salt (I-795) ~ Salt (I-798), Salt (I-799) ~ Salt (I-802), Salt (I-805) ~ Salt (I-809), Salt (I-812) ~ Salt (I-828), Salt (I-833) ~ Salt (I-836), Salt (I-837) ~ Salt (I-840), Salt (I- 843) ~ Salt (I-847), Salt (I-850) ~ Salt (I-866), Salt (I-871) ~ Salt (I-874), Salt (I-875) ~ Salt (I-878), Salt (I-881) ~ Salt (I-885), Salt (I-888) ~ Salt (I-904), Salt (I-909) ~ Salt (I-912), Salt ( I-913) ~ Salt (I-916), Salt (I-919) ~ Salt (I-923), Salt (I-926) ~ Salt (I-942), Salt (I-947) ~ Salt (I-950), Salt (I-951) ~ Salt (I-954), Salt (I-957) ~ Salt (I-961), Salt (I-964) ~ Salt (I-980),Salts (I-985) to (I-988), salts (I-989) to (I-992), salts (I-995) to (I-999), salts (I-1002) to (I-1018), salts (I-1023) to (I-1026), salts (I-1027) to (I-1030), salts (I-1033) to (I-1037), salts (I-1040) to (I-1056), salts (I-1061) to (I-1064), salts (I-1065) to (I-1068), salts (I-1071) to (I-1075), salts (I-1078) to (I-1094), salts (I-1099) to (I-1102), salts (I-1103) to (I-1106), salts (I-1109) to (I-1113), salts (I-1116) to (I-1132), salts (I-1137) to (I-1140), salts (I-1141) to (I-1144), salts (I-1147) to (I-1151), salts (I-1154) to (I-1170), salts (I-1175) to (I-1178), salts (I-1179) to (I-1182), salts (I-1185) to (I-1189), salts (I-1192) to (I-1208), salts (I-1213) to (I-1216), salts (I-1217) to (I-1220), salts (I-1223) to (I-1227), salts (I-1230) to (I-1246), salts (I-1251) to (I-1254), salts (I-1255) to (I-1258), salts (I-1261) to (I-1265), salts (I-1268) to (I-1284), salts (I-1289) to (I-1292), salts (I-1293) to (I-1296), salts (I-1299) to (I-1303), salts (I-1306) to (I-1322), salts (I-1327) to (I-1330), salts (I-1331) to (I-1334), salts (I-1337) to (I-1341), salts (I-1344) to (I-1360), salts (I-1365) to (I-1368), salts (I-1369) to (I-1372), salts (I-1375) to (I-1379), salts (I-1382) to (I-1398), salts (I-1403) to (I-1406), salts (I-1407) to (I-1410), salts (I-1413) to (I-1417), salts (I-1420) to (I-1436), salts (I-1441) to (I-1444), salts (I-1445) to (I-1448)It is preferable that they are salts (I-1451) to salts (I-1455), salts (I-1458) to salts (I-1474), salts (I-1479) to salts (I-1482), salts (I-1483) to salts (I-1486), salts (I-1489) to salts (I-1493), salts (I-1496) to salts (I-1512), salts (I-1517) to salts (I-1520).

[0068] <Method for Producing Salt (I)> Salt (I) can be produced by reacting a salt represented by formula (I-a) with a salt represented by formula (I-b) in a solvent. TIFF0007716229000049.tif66162[wherein all the symbols have the same meanings as described above. R A , R B and R C each independently represents a hydrocarbon group having 1 to 12 carbon atoms, or R A , R B and R C may together form an aromatic ring. R D represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms.] Examples of the solvent include chloroform, monochlorobenzene, acetonitrile, water and the like. The reaction temperature is usually 15°C to 80°C, and the reaction time is usually 0.5 to 24 hours.

[0069] Examples of the salt represented by formula (I-b) include salts represented by the following formula. These salts can be easily produced by the same method as the method described in JP-A-2011-116747 and JP-A-2016-047815, or by a known production method. TIFF0007716229000050.tif198162

[0070] In salt (I-a), R 1 and R 2 are -O-L 1 -CO-O-R 10The salt represented by formula (I-a1) can be produced by reacting a salt represented by formula (Ic) with a compound represented by formula (Id) in a solvent in the presence of a base catalyst. TIFF0007716229000051.tif59157 [wherein all symbols have the same meanings as defined above.] Examples of the base include potassium carbonate, potassium iodide, pyridine, and triethylamine. Examples of the solvent include chloroform, monochlorobenzene, dimethylformamide, acetonitrile, ethyl acetate, and water. The reaction temperature is usually 15° C. to 80° C., and the reaction time is usually 0.5 to 24 hours.

[0071] Examples of compounds represented by formula (Id) include the compounds represented below, which are readily available on the market and can also be easily produced by known production methods. TIFF0007716229000052.tif29107

[0072] The salt represented by formula (Ic) can be produced by reacting the salt represented by formula (Ie), a compound represented by formula (I-f1), and a compound represented by formula (I-f2) in a solvent in the presence of a catalyst. TIFF0007716229000053.tif70161 [wherein all symbols have the same meanings as defined above.] Examples of the catalyst include potassium carbonate and sodium hydride. Examples of the solvent include chloroform, monochlorobenzene, acetonitrile, and water. The reaction temperature is usually 15° C. to 100° C., and the reaction time is usually 0.5 to 24 hours.

[0073] Examples of the salt represented by formula (Ie) include salts represented by the following formula, which are readily available on the market and can be easily produced by known production methods. TIFF0007716229000054.tif41152

[0074] Examples of the compound represented by formula (I-f1) and the compound represented by formula (I-f2) include the compounds represented below, which are readily available on the market. TIFF0007716229000055.tif20104

[0075] The salt represented by formula (Ic) can also be produced by reacting the salt represented by formula (Ie), a compound represented by formula (I-f4), and a compound represented by formula (I-f5) in a solvent in the presence of potassium carbonate, followed by acid treatment. TIFF0007716229000056.tif76155 [wherein all symbols have the same meanings as defined above.] R ac represents an acid labile group. Examples of the solvent include chloroform, monochlorobenzene, acetonitrile, and water. The reaction temperature is usually 15° C. to 100° C., and the reaction time is usually 0.5 to 24 hours. The acid includes p-toluenesulfonic acid, hydrochloric acid, and the like.

[0076] Examples of the compound represented by formula (I-f4) and the compound represented by formula (I-f5) include the compounds represented by the following formulae, which are readily available on the market. TIFF0007716229000057.tif81153

[0077] In the salt (Ia), R 1 and R 2 But, -OR 10 The salt represented by formula (I-a2) can be produced by reacting a salt represented by formula (Ic) with a compound represented by formula (I-d2) in a solvent in the presence of a base catalyst. TIFF0007716229000058.tif63159 [wherein all symbols have the same meanings as defined above.] Examples of the base include sodium hydroxide and potassium hydroxide. Examples of the solvent include chloroform, monochlorobenzene, dimethylformamide, acetonitrile, ethyl acetate, and water. The reaction temperature is generally 15°C to 80°C, and the reaction time is generally 0.5 to 24 hours.

[0078] Examples of the compound represented by the formula (I-d2) include the compounds represented below, which can be easily obtained from the market and can also be easily produced by known production methods. TIFF0007716229000059.tif2297

[0079] In the salt (I-a), R 1 and R 2 The salt in which is -O-CO-O-R 10 (the salt represented by the formula (I-a3)) can be produced by reacting the salt represented by the formula (I-c) with the compound represented by the formula (I-d2) in a solvent in the presence of carbonyldiimidazole. TIFF0007716229000060.tif64165 [In the formula, all the symbols have the same meanings as described above.] Examples of the solvent include chloroform, monochlorobenzene, dimethylformamide, acetonitrile, ethyl acetate, and water. The reaction temperature is generally 15°C to 80°C, and the reaction time is generally 0.5 to 24 hours.

[0080] In the salt (I-a), R 1 and R 2 and The salt in which is -O-CO-R 10 (the salt represented by the formula (I-a4)) can be produced by reacting the salt represented by the formula (I-c) with the compound represented by the formula (I-d4) in a solvent in the presence of a base catalyst. TIFF0007716229000061.tif65160 [In the formula, all the symbols have the same meanings as described above.] Examples of the base include potassium carbonate, potassium iodide, pyridine, and triethylamine. Examples of the solvent include chloroform, monochlorobenzene, dimethylformamide, acetonitrile, ethyl acetate, and water. The reaction temperature is generally 15°C to 80°C, and the reaction time is generally 0.5 to 24 hours.

[0081] Examples of the compound represented by the formula (I-d4) include the compounds represented below, which can be easily obtained from the market and can also be easily produced by known production methods. TIFF0007716229000062.tif2996

[0082] [Acid generator] The acid generator of the present invention is an acid generator containing the salt (I). It may contain one kind of the salt (I) or two or more kinds of the salt (I). In addition to the salt (I), the acid generator of the present invention may contain an acid generator known in the resist field (hereinafter sometimes referred to as "acid generator (B)"). The acid generator (B) may be used alone or in combination of two or more kinds.

[0083] Either a nonionic or ionic acid generator (B) may be used. Examples of the nonionic acid generator 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), etc. Representative examples of the ionic acid generator 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, sulfonylimide anion, sulfonylmethide anion, etc.

[0084] As the acid generator (B), compounds that generate an acid upon irradiation, which are described in, for example, JP-A-63-26653, JP-A-55-164824, JP-A-62-69263, JP-A-63-146038, JP-A-63-163452, JP-A-62-153853, JP-A-63-146029, U.S. Patent No. 3,779,778, U.S. Patent No. 3,849,137, German Patent No. 3914407, European Patent No. 126,712, etc., can be used. Further, compounds produced by known methods may also be used. The acid generator (B) may be used in combination of two or more kinds.

[0085] The acid generator (B) is preferably a fluorine-containing acid generator, and more preferably a salt represented by the formula (B1) (hereinafter sometimes referred to as "acid generator (B1)". However, salt (I) is excluded.). TIFF0007716229000063.tif2963[In the formula (B1), Q b1 and Q b2 each independently represents a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms. L b1 represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, and -CH2- contained in the divalent saturated hydrocarbon group may be replaced by -O- or -CO-, and a hydrogen atom contained in the divalent saturated hydrocarbon group may be replaced by a fluorine atom or a hydroxy group. Y represents a methyl group which may have a substituent or an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and -CH2- contained in the alicyclic hydrocarbon group may be replaced by -O-, -SO2- or -CO-. Z1 + represents an organic cation.]

[0086] Q in the formula (B1) b1 , Q b2 , L b1 and Y are the same as Q 1 , Q 2 , L 1 and Y 1 in the above-described formula (I-A), respectively. Examples of the sulfonic acid anion in formula (B1) include the same anions as those represented by formula (I-A).

[0087] Z1 + Examples of the organic cation of include organic onium cations, organic sulfonium cations, organic iodonium cations, organic ammonium cations, benzothiazolium cations, and organic phosphonium cations. Among these, organic sulfonium cations and organic iodonium cations are preferred, and arylsulfonium cations are more preferred.

[0088] Z + Examples of the organic cation of include organic onium cations, organic sulfonium cations, organic iodonium cations, organic ammonium cations, benzothiazolium cations, and organic phosphonium cations. Among these, organic sulfonium cations and organic iodonium cations are preferred, and arylsulfonium cations are more preferred. Specifically, cations represented by any of formulas (b2-1) to (b2-4) (hereinafter, may be referred to as "cation (b2-1)" etc. according to the formula number) are included.

[0089] In formulas (b2-1) to (b2-4), R b4 ~R b6each independently represent a chain hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, or an aromatic hydrocarbon group having 6 to 36 carbon atoms, a hydrogen atom contained in the chain hydrocarbon group may be substituted with a hydroxy group, an alkoxy group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms, a hydrogen atom contained in the alicyclic hydrocarbon group may be substituted with a halogen atom, an aliphatic hydrocarbon group having 1 to 18 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, or a glycidyloxy group, and a hydrogen atom contained in the aromatic hydrocarbon group may be substituted with a halogen atom, a hydroxy group, an aliphatic hydrocarbon group having 1 to 18 carbon atoms, a fluorinated alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. R b4 and R b5 and may be bonded to each other to form a ring together with the sulfur atom to which they are attached, and -CH2- contained in the ring may be replaced with -O-, -S- or -CO-. R b7 and R b8 each independently represents a halogen atom, a hydroxy group, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. m2 and n2 each independently represent an integer of 0 to 5; When m2 is 2 or more, multiple R b7 may be the same or different, and when n2 is 2 or more, multiple R b8 may be the same or different. R b9 and R b10 each independently represents a chain hydrocarbon group having 1 to 36 carbon atoms or an alicyclic hydrocarbon group having 3 to 36 carbon atoms. R b9 and R b10 and may be bonded to each other to form a ring together with the sulfur atom to which they are attached, and -CH2- contained in the ring may be replaced with -O-, -S- or -CO-. R b11 represents a hydrogen atom, a chain hydrocarbon group having 1 to 36 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms. Rb12 represents a chain hydrocarbon group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms, and the hydrogen atoms contained in the chain hydrocarbon group may be substituted with an aromatic hydrocarbon group having 6 to 18 carbon atoms, and the hydrogen atoms contained in the aromatic hydrocarbon group may be substituted with an alkoxy group having 1 to 12 carbon atoms or an alkylcarbonyloxy group having 1 to 12 carbon atoms. R b11 and R b12 may be bonded to each other to form a ring including -CH-CO- to which they are bonded, and -CH2- contained in the ring may be replaced with -O-, -S- or -CO-. R b13 ~R b18 each independently represents a halogen atom, a hydroxy group, an aliphatic hydrocarbon group having 1 to 12 carbon atoms, a fluorinated alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms. L b31 represents a sulfur atom or an oxygen atom. o2, p2, s2, and t2 each independently represent an integer of any one of 0 to 5. q2 and r2 each independently represent an integer of any one of 0 to 4. u2 represents 0 or 1. When o2 is 2 or more, a plurality of R b13 are the same or different, when p2 is 2 or more, a plurality of R b14 are the same or different, when q2 is 2 or more, a plurality of R b15 are the same or different, when r2 is 2 or more, a plurality of R b16 are the same or different, when s2 is 2 or more, a plurality of R b17 are the same or different, when t2 is 2 or more, a plurality of R b18 are the same or different. The aliphatic hydrocarbon group represents a chain hydrocarbon group and an alicyclic hydrocarbon group. Examples of the chain hydrocarbon group include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, octyl group, and 2-ethylhexyl group. In particular, Rb9 ~R b12 The chain hydrocarbon group of ~R preferably has 1 to 12 carbon atoms. The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclodecyl group and the like. Examples of the polycyclic alicyclic hydrocarbon group include decahydronaphthyl group, adamantyl group, norbornyl group and the following groups and the like. TIFF0007716229000065.tif10158 In particular, R b9 ~R b12 The alicyclic hydrocarbon group of ~R preferably has 3 to 18 carbon atoms, more preferably 4 to 12 carbon atoms. Examples of the alicyclic hydrocarbon group in which a hydrogen atom is substituted with an aliphatic hydrocarbon group include methylcyclohexyl group, dimethylcyclohexyl group, 2-methyladamantan-2-yl group, 2-ethyladamantan-2-yl group, 2-isopropyladamantan-2-yl group, methylnorbornyl group, isobornyl group and the like. In the alicyclic hydrocarbon group in which a hydrogen atom is substituted with an aliphatic hydrocarbon group, the total number of carbon atoms of the alicyclic hydrocarbon group and the aliphatic hydrocarbon group is preferably 20 or less. The alkyl fluoride group represents an alkyl group having 1 to 12 carbon atoms and having a fluorine atom, and examples thereof include fluoromethyl group, difluoromethyl group, trifluoromethyl group, perfluorobutyl and the like. The number of carbon atoms of the alkyl fluoride group is preferably 1 to 9, more preferably 1 to 6, and still more preferably 1 to 4.

[0090] Examples of the aromatic hydrocarbon group include aryl groups such as phenyl group, biphenyl group, naphthyl group, and phenanthryl group. The aromatic hydrocarbon group may have a chain hydrocarbon group or an alicyclic hydrocarbon group, and examples of the aromatic hydrocarbon group having a chain hydrocarbon group with 1 to 18 carbon atoms include (tolyl group, xylyl group, cumenyl group, mesityl group, p-ethylphenyl group, p-tert-butylphenyl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group, etc.), and examples of the aromatic hydrocarbon group having an alicyclic hydrocarbon group with 3 to 18 carbon atoms include (p-cyclohexylphenyl group, p-adamantylphenyl group, etc.). When the aromatic hydrocarbon group has a chain hydrocarbon group or an alicyclic hydrocarbon group, a chain hydrocarbon group with 1 to 18 carbon atoms and an alicyclic hydrocarbon group with 3 to 18 carbon atoms are preferred. Examples of the aromatic hydrocarbon group in which a hydrogen atom is substituted with an alkoxy group include p-methoxyphenyl group. Examples of the chain hydrocarbon group in which a hydrogen atom is substituted with an aromatic hydrocarbon group include aralkyl groups such as benzyl group, phenethyl group, phenylpropyl group, trityl group, naphthylmethyl group, and naphthylethyl group. Examples of the alkoxy group include methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, decyloxy group, and dodecyloxy group. Examples of the alkylcarbonyl group include acetyl group, propionyl group, and butyryl group. Examples of the halogen atom include fluorine atom, chlorine atom, bromine atom, and iodine atom. Examples of the alkylcarbonyloxy group include methylcarbonyloxy group, ethylcarbonyloxy group, propylcarbonyloxy group, isopropylcarbonyloxy group, butylcarbonyloxy group, sec-butylcarbonyloxy group, tert-butylcarbonyloxy group, pentylcarbonyloxy group, hexylcarbonyloxy group, octylcarbonyloxy group, and 2-ethylhexylcarbonyloxy group. R b4 and R b5and bond to each other and form a ring together with the sulfur atom to which they are bonded, which may be a monocyclic, polycyclic, aromatic, non-aromatic, saturated, or unsaturated ring. This ring may be a ring having 3 to 18 carbon atoms, preferably a ring having 4 to 18 carbon atoms. Furthermore, the ring containing a sulfur atom may be a 3- to 12-membered ring, preferably a 3- to 7-membered ring, for example, the following rings. * represents a bond. TIFF0007716229000066.tif23143R b9 and R b10 The ring formed by these together may be any of monocyclic, polycyclic, aromatic, non-aromatic, saturated and unsaturated rings. This ring may be a 3- to 12-membered ring, preferably a 3- to 7-membered ring. Examples thereof include a thiolan-1-ium ring (tetrahydrothiophenium ring), a thian-1-ium ring, and a 1,4-oxathian-4-ium ring. R b11 and R b12 The ring formed by combining these may be any of monocyclic, polycyclic, aromatic, non-aromatic, saturated and unsaturated rings. Examples of this ring include a 3- to 12-membered ring, and preferably a 3- to 7-membered ring. Examples include an oxocycloheptane ring, an oxocyclohexane ring, an oxonorbornane ring, and an oxoadamantane ring.

[0091] Among the cations (b2-1) to (b2-4), the cation (b2-1) is preferred. Examples of the cation (b2-1) include the following cations. TIFF0007716229000067.tif79158

[0092] TIFF0007716229000068.tif108166

[0093] Examples of the cation (b2-2) include the following cations. TIFF0007716229000069.tif18150

[0094] Examples of the cation (b2-3) include the following cations. TIFF0007716229000070.tif26140

[0095] Examples of the cation (b2-4) include the following cations. TIFF0007716229000071.tif62164

[0096] TIFF0007716229000072.tif70158

[0097] The acid generator (B) is a combination of the above-mentioned anion and the above-mentioned organic cation, and these can be arbitrarily combined. As the acid generator (B), preferably, an anion represented by any of the formulas (I-a-1) to (I-a-3), (I-a-7) to (I-a-16), (I-a-18), (I-a-19), (I-a-22) to (I-a-38) exemplified as the anion represented by the formula (I-A), and a combination with the cation (b2-1), the cation (b2-3) or the cation (b2-4) are mentioned.

[0098] Examples of the acid generator (B) preferably include those represented by the formulas (B1-1) to (B1-56), and among them, those containing an arylsulfonium cation are preferable, and those represented by the formulas (B1-1) to (B1-3), (B1-5) to (B1-7), (B1-11) to (B1-14), (B1-20) to (B1-26), (B1-29), (B1-31) to (B1-56) are particularly preferable. TIFF0007716229000073.tif98161

[0099] TIFF0007716229000074.tif152165

[0100] TIFF0007716229000075.tif92158

[0101] TIFF0007716229000076.tif144161

[0102] TIFF0007716229000077.tif62163

[0103] TIFF0007716229000078.tif92158

[0104] When the acid generator contains a salt (I) and an acid generator (B), the ratio of the salt (I) to the acid generator (B) (mass ratio; salt (I):acid generator (B)) is usually 1:99 to 99:1, preferably 2:98 to 98:2, more preferably 5:95 to 95:5, even more preferably 10:90 to 90:10, and particularly preferably 15:85 to 85:15. In the resist composition of the present invention, the total content of the acid generators is preferably 1 part by mass to 45 parts by mass, and more preferably 3 parts by mass to 40 parts by mass, per 100 parts by mass of the resin (A) described below.

[0105] [Resist Composition] The resist composition of the present invention contains an acid generator containing a salt (I) and a resin having an acid labile group (hereinafter sometimes referred to as "resin (A)"). Here, the "acid labile group" refers to a group that has a leaving group and that is eliminated upon contact with an acid, converting the structural unit into a structural unit having a hydrophilic group (e.g., a hydroxy group or a carboxy group). The resist composition of the present invention preferably contains a quencher such as a salt that generates an acid with a weaker acidity than the acid generated from the acid generator (hereinafter may be referred to as "quencher (C)"), and preferably contains a solvent (hereinafter may be referred to as "solvent (E)").

[0106] <Resin (A)> Resin (A) has a structural unit having an acid-labile group (hereinafter sometimes referred to as "structural unit (a1)"). Resin (A) preferably further contains a structural unit other than structural unit (a1). Examples of the structural unit other than structural unit (a1) include a structural unit having no acid-labile group (hereinafter sometimes referred to as "structural unit (s)"), a structural unit other than structural unit (a1) and structural unit (s) (for example, a structural unit having a halogen atom described later (hereinafter sometimes referred to as "structural unit (a4)"), a structural unit having a non-leaving hydrocarbon group described later (hereinafter sometimes referred to as "structural unit (a5)"), and a structural unit derived from other monomers known in the art, etc.).

[0107] 〈Structural unit (a1)〉 Structural unit (a1) is derived from a monomer having an acid-labile group (hereinafter sometimes referred to as "monomer (a1)"). The acid-labile group contained in resin (A) is preferably a group represented by formula (1) (hereinafter also referred to as group (1)) and / or a group represented by formula (2) (hereinafter also referred to as group (2)). TIFF0007716229000079.tif2298[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. ma and na each independently represent 0 or 1, and at least one of ma and na represents 1. * represents a bond.] TIFF0007716229000080.tif2378[In formula (2), R a1’ and R a2’ each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, R a3’ represents a hydrocarbon group having 1 to 20 carbon atoms, or R a2’ and R a3’are bonded to each other to form a heterocyclic group having 3 to 20 carbon atoms together with the carbon atoms to which they are bonded and X, and the -CH2- contained in the hydrocarbon group and the heterocyclic group may be replaced by -O- or -S-. X represents an oxygen atom or a sulfur atom. na’ represents 0 or 1. * represents a bond.]

[0108] R a1 、R a2 and R a3 Examples of the alkyl group in include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group and the like. R a1 、R a2 and R a3 Examples of the alkenyl group in include ethenyl group, propenyl group, isopropenyl group, butenyl group, isobutenyl group, tert-butenyl group, pentenyl group, hexenyl group, heptenyl group, octynyl group, isooctynyl group, nonenyl group. R a1 、R a2 and R a3 The alicyclic hydrocarbon group in may be either monocyclic or polycyclic. Examples of the monocyclic alicyclic hydrocarbon group include cycloalkyl groups such as cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and the like. Examples of the polycyclic alicyclic hydrocarbon group include decahydronaphthyl group, adamantyl group, norbornyl group and the following groups (* represents a bond.). The carbon number of the alicyclic hydrocarbon group of R a1 、R a2 and R a3 is preferably 3 to 16. TIFF0007716229000081.tif10159R a1 、R a2 and R a3 Examples of the aromatic hydrocarbon group in include aryl groups such as phenyl group, naphthyl group, anthryl group, biphenyl group, phenanthryl group and the like. Examples of the combined group include a group combining the above-described alkyl group and alicyclic hydrocarbon group (e.g., alkylcycloalkyl group or cycloalkylalkyl group), aralkyl group such as benzyl group, 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.), aromatic hydrocarbon group having an alicyclic hydrocarbon group (p-cyclohexylphenyl group, p-adamantylphenyl group, etc.), aryl-cycloalkyl group such as phenylcyclohexyl group, etc. 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 a bond to -O-. TIFF0007716229000082.tif35157

[0109] R a1’ 、R a2’ and R a3’ Examples of the hydrocarbon group in R The alkyl group and alicyclic hydrocarbon group are the same as those exemplified for R a1 、R a2 and R a3 . Examples of the aromatic hydrocarbon group include aryl groups such as phenyl group, naphthyl group, anthryl group, biphenyl group, phenanthryl group, etc. Examples of the combined group include a group combining the above-described alkyl group and alicyclic hydrocarbon group (e.g., alkylcycloalkyl group or cycloalkylalkyl group), aralkyl group such as benzyl group, 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.), aromatic hydrocarbon group having an alicyclic hydrocarbon group (p-cyclohexylphenyl group, p-adamantylphenyl group, etc.), aryl-cycloalkyl group such as phenylcyclohexyl group, and the like. R a2’ and R a3’ When R and R 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’ includes the following groups. * represents a bond. TIFF0007716229000083.tif18124R a1’ and R a2’ Among them, at least one is preferably a hydrogen atom. na' is preferably 0.

[0110] Examples of the group (1) include the following groups. In formula (1), a group in which R a1 , R a2 and R a3 are alkyl groups, ma = 0, and na = 1. As the group, a tert-butoxycarbonyl group is preferable. In formula (1), a group in which R a1 , R a2 together with the carbon atom to which they are bonded form an adamantyl group, and R a3 is an alkyl group, ma = 0, and na = 1. In formula (1), a group in which R a1 and R a2 are each independently an alkyl group, R a3 is an adamantyl group, ma = 0, and na = 1. Examples of the group (1) specifically include the following groups. * represents a bond. TIFF0007716229000084.tif170163

[0111] Specific examples of the group (2) include the following groups. * represents a bond. TIFF0007716229000085.tif68162

[0112] 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.

[0113] Among the (meth)acrylic monomers having an acid-labile group, those having an alicyclic hydrocarbon group with 5 to 20 carbon atoms are preferably included. 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.

[0114] As the structural unit derived from the (meth)acrylic monomer having the group (1), preferably, a structural unit represented by the formula (a1-0) (hereinafter, may be referred to as a structural unit (a1-0)), a structural unit represented by the formula (a1-1) (hereinafter, may be referred to as a structural unit (a1-1)), or a structural unit represented by the formula (a1-2) (hereinafter, may be referred to as a structural unit (a1-2)) is included. More preferably, it is at least one or two structural units selected from the group consisting of the structural unit (a1-1) and the structural unit (a1-2). These may be used alone or in combination of two or more. TIFF0007716229000086.tif46149[In the formula (a1-0), the formula (a1-1), and the formula (a1-2), L a01 、L a1 and L a2 each independently represents -O- or *-O-(CH2) k1 -CO-O-, k1 represents an integer of any one of 1 to 7, and * represents a bond to -CO-. R a01 、R a4 and R a5 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a02 、R a03 and R a04 each independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these. R a6 and R a7 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these. m1 represents any integer from 0 to 14. n1 represents any integer from 0 to 10. n1’ represents any integer from 0 to 3.

[0115] R a01 、R a4 and R a5 are preferably a hydrogen atom or a methyl group, and more preferably a methyl group. L a01 、L a1 and L a2 are preferably an oxygen atom or *-O-(CH2) k01 -CO-O- (wherein k01 is preferably any integer from 1 to 4, more preferably 1), and more preferably an oxygen atom. 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 formed by combining these in a1 、R a2 and R a3 are the same as the groups exemplified by R R a02 、R a03, and R a04 The alkyl group in a04 is preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group or an ethyl group, and still more preferably a methyl group. R a6 and R a7 The alkyl group in a7 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 still more preferably an ethyl group, an isopropyl group or a t-butyl group. R a6 and R a7 The alkenyl group in a7 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. R a02 , R a03 , R a04 , R a6 and R a7 The number of carbon atoms of the alicyclic hydrocarbon group of a7 is preferably 5 to 12, 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 a7 is preferably 6 to 12, more preferably 6 to 10. The group formed by combining an alkyl group and an alicyclic hydrocarbon group preferably has a total number of carbon atoms of 18 or less when these alkyl group and alicyclic hydrocarbon group are combined. The group formed by combining an alkyl group and an aromatic hydrocarbon group preferably has a total number of carbon atoms of 18 or less when these alkyl group and aromatic hydrocarbon group are combined. R a02 and R a03 are preferably an alkyl group having 1 to 6 carbon atoms or an aromatic hydrocarbon group having 6 to 12 carbon atoms, more preferably a methyl group, an ethyl group, a phenyl group or a naphthyl group. R a04 is preferably an alkyl group having 1 to 6 carbon atoms or an alicyclic hydrocarbon group having 5 to 12 carbon atoms, more preferably a methyl group, an ethyl group, a cyclohexyl group or an adamantyl group. R a6 and R a7 is preferably an alkyl group having 1 to 6 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, or an aromatic hydrocarbon group having 6 to 12 carbon atoms, 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, and still more preferably an ethyl group, an isopropyl group, a t-butyl group, an ethenyl group or a phenyl group. 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. n1' is preferably 0 or 1.

[0116] Examples of the structural unit (a1-0) include a structural unit represented by any of the formulas (a1-0-1) to (a1-0-18) and a methyl group corresponding to R in the structural unit (a1-0) a01 which is replaced by a hydrogen atom, a halogen atom, a haloalkyl group (an alkyl group having a halogen atom) or another alkyl group, and a structural unit represented by any of the formulas (a1-0-1) to (a1-0-10), (a1-0-13), (a1-0-14) is preferable. TIFF0007716229000087.tif100167

[0117] Examples of the structural unit (a1-1) include a structural unit derived from the monomer described in JP-A-2010-204646. Among them, a structural unit represented by any of the formulas (a1-1-1) to (a1-1-7) and a structural unit in which the methyl group corresponding to R in the structural unit (a1-1) a4 is replaced by a hydrogen atom is preferable, and a structural unit represented by any of the formulas (a1-1-1) to (a1-1-4) is more preferable. TIFF0007716229000088.tif39167

[0118] The structural unit (a1-2) includes a structural unit represented by any one of formulas (a1-2-1) to (a1-2-14) and R a5 and structural units in which the methyl group corresponding to the formula (a1-2-1) is replaced with a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group, and structural units represented by any of formulas (a1-2-2), (a1-2-5), (a1-2-6), and (a1-2-10) to (a1-2-14) are preferred. TIFF0007716229000089.tif67163

[0119] When the resin (A) contains the structural unit (a1-0), the content thereof is usually 5 to 60 mol %, preferably 5 to 50 mol %, and more preferably 10 to 40 mol %, based on all structural units in the resin (A). When the resin (A) contains the structural unit (a1-1) and / or the structural unit (a1-2), the total content thereof is usually 10 to 95 mol %, preferably 15 to 90 mol %, more preferably 20 to 85 mol %, even more preferably 25 to 70 mol %, and still more preferably 30 to 70 mol %, based on all structural units in the resin (A).

[0120] An example of the structural unit (a1) having the group (2) is a structural unit represented by formula (a1-4) (hereinafter, sometimes referred to as "structural unit (a1-4)"). TIFF0007716229000090.tif3854[In formula (a1-4), R a32 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a33 represents a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group, or a methacryloyloxy group. A a30 is a single bond or* -X a31 -(A a32 -X a32 ) nc - represents, and * represents the bonding site with the carbon atom to which -R a32 is bonded. A a32 represents an alkanediyl group having 1 to 6 carbon atoms. X a31 and X a32 each independently represent -O-, -CO-O- or -O-CO-. nc represents 0 or 1. la represents any integer from 0 to 4. When la is any integer of 2 or more, a plurality of R a33 may be the same as or different from each other. R a34 and R a35 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, and 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 -CH2- contained in the hydrocarbon group and the divalent hydrocarbon group may be replaced by -O- or -S-.

[0121] R a32 and R a33 Examples of the halogen atom in R R a32 include a fluorine atom, a chlorine atom, a bromine atom and the like. Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom in R R a32 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group. R a33 Examples of the alkyl group in R a33 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. R a33 Examples of the alkoxyalkyl group in R a33 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. R a33 Examples of the alkylcarbonyl group in R a33Examples 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. R a33 is preferably a halogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group, or an ethoxymethoxy group, and even more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, or an ethoxyethoxy group.

[0122] *-X a31 -(A a32 -X a32 ) nc Examples of - include *-O-, *-CO-O-, *-O-CO-, *-CO-O-A a32 -CO-O-, *-O-CO-A a32 -O-, *-O-A a32 -CO-O-, *-CO-O-A a32 -O-CO-, *-O-CO-A a32 -O-CO- are included. Among them, *-CO-O-, *-CO-O-A a32 -CO-O- or *-O-A a32 -CO-O- is preferred.

[0123] Examples of the 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 pentane-1,5-diyl group, a hexane-1,6-diyl group, a butane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. A a32 is preferably a methylene group or an ethylene group.

[0124] A a30is a single bond, *-CO-O- or *-CO-O-A a32 -CO-O- is preferred, more preferably a single bond, *-CO-O- or *-CO-O-CH2-CO-O-, and even more preferably a single bond or *-CO-O-.

[0125] la is preferably 0, 1 or 2, more preferably 0 or 1, and even more preferably 0. R a34 、R a35 and R a36 Examples of the hydrocarbon group in include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group combining these. 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, a cyclooctyl group, and the like. Examples of the polycyclic alicyclic hydrocarbon group include a decahydronaphthyl group, an adamantyl group, a norbornyl group, and the following group (* represents the bonding site). TIFF0007716229000091.tif10151Examples of the aromatic hydrocarbon group include aryl groups such as a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, a phenanthryl group, and the like. Examples of the combined group include a group combining the above-described alkyl group and alicyclic hydrocarbon group (e.g., a cycloalkylalkyl group), an aralkyl group such as a 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 a phenylcyclohexyl group, and the like. In particular, R a36Examples thereof include an alkyl group having 1 to 18 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these groups.

[0126] 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, more preferably a methyl group or an ethyl group. R a36 The hydrocarbon group of R is preferably an alkyl group having 1 to 18 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group formed by combining these groups, more preferably an alkyl group having 1 to 18 carbon atoms, an alicyclic aliphatic hydrocarbon group having 3 to 18 carbon atoms, or an aralkyl group having 7 to 18 carbon atoms. The alkyl group and the 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.

[0127] -OC(R a34 )(R a35 )-O-R a36 in the structural unit (a1-4) is desorbed upon contact with an acid (e.g., p-toluenesulfonic acid) to form a hydroxy group. -OC(R a34 )(R a35 )-O-R a36 is preferably bonded to the o-position or p-position of the benzene ring, more preferably to the p-position.

[0128] Examples of the structural unit (a1-4) include structural units derived from the monomers described in JP-A-2010-204646. Preferably, the structural units represented by formula (a1-4-1) to formula (a1-4-18) and R in the structural unit (a1-4) a32Examples of the structural unit in which the hydrogen atom corresponding to the following is replaced with a halogen atom, a haloalkyl group or an alkyl group include, more preferably, structural units represented by formula (a1-4-1) to formula (a1-4-5), formula (a1-4-10), formula (a1-4-13), and formula (a1-4-14). TIFF0007716229000092.tif100166

[0129] When the resin (A) has the structural unit (a1-4), its content is preferably 10 to 95 mol%, more preferably 15 to 90 mol%, still more preferably 20 to 85 mol%, still more preferably 20 to 70 mol%, and particularly preferably 20 to 60 mol% with respect to the total of all the structural units of the resin (A).

[0130] Examples of the structural unit derived from the (meth)acrylic monomer having the group (2) also include a structural unit represented by formula (a1-5) (hereinafter sometimes referred to as "structural unit (a1-5)"). TIFF0007716229000093.tif4253In 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 represents a single bond or *-(CH2) h3 -CO-L 54 -, h3 represents an integer of 1 to 4, and * represents a bond to L 51 . 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.

[0131] Examples of the halogen atom include a fluorine atom and a chlorine atom, and a fluorine atom is preferred. Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, fluoromethyl group and trifluoromethyl group. 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. L 52 and L 53 Among them, it is preferable that one of them is -O- and the other is -S-. s1 is preferably 1. s1’ is preferably any integer from 0 to 2. Z a1 is preferably a single bond or *-CH2-CO-O-.

[0132] 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. TIFF0007716229000094.tif31130

[0133] When the resin (A) has the structural unit (a1-5), its content is preferably 1 to 50 mol%, more preferably 3 to 45 mol%, still more preferably 5 to 40 mol%, and still more preferably 5 to 30 mol% based on all the structural units of the resin (A).

[0134] In addition, examples of the structural unit (a1) also include the following structural units. TIFF0007716229000095.tif27161

[0135] When the resin (A) contains structural units such as the above (a1-3-1) to (a1-3-7), the content thereof 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 particularly preferably 20 to 60 mol% based on all the structural units of the resin (A).

[0136] 〈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. The structural unit(s) preferably has a hydroxy group or a lactone ring. By using a resin having a structural unit having a hydroxy group and no acid-labile group (hereinafter sometimes referred to as "structural unit (a2)") and / or a structural unit having a lactone ring and no 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.

[0137] 〈Structural unit (a2)〉 The hydroxy group of the structural unit (a2) may be an alcoholic hydroxy group or a phenolic hydroxy group. 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. 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 (a2-1) described later. The structural unit (a2) may be contained alone or in combination of two or more.

[0138] Examples of the structural unit having a phenolic hydroxy group in the structural unit (a2) include a structural unit represented by the formula (a2-A) (hereinafter sometimes referred to as "structural unit (a2-A)"). TIFF0007716229000096.tif4652[In the formula (a2-A), R a50 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a51 represents a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group, or a methacryloyloxy group. A a50 represents a single bond or *-X a51 -(A a52 -X a52 ) nb - and * represents a bond with the carbon atom to which -R a50 is bonded. A a52 represents an alkanediyl group having 1 to 6 carbon atoms. X a51 and X a52 each independently represents -O-, -CO-O-, or -O-CO-. nb represents 0 or 1. mb represents any integer from 0 to 4. When mb is an integer of 2 or more, a plurality of R a51 may be the same as or different from each other.]

[0139] R a50 and R a51 Examples of the halogen atom in include a fluorine atom, a chlorine atom, and a bromine atom, etc. R a50Examples 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 and perfluorohexyl group. R a50 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, and even more preferably a hydrogen atom or a methyl group. R a51 Examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group and hexyl group. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. R a51 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 a methoxy group or an ethoxy group, and even more preferably a methoxy group. R a51 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 even more preferably a methoxymethyl group. R a51Examples of the alkoxyalkoxy group in [[ ]] include a methoxymethoxy group, a methoxyethoxy group, an ethoxymethoxy group, an ethoxyethoxy group, a propoxymethoxy group, an isopropoxymethoxy group, a butoxymethoxy group, a sec-butoxymethoxy group, and a tert-butoxymethoxy group. The alkoxyalkoxy group is preferably an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a methoxyethoxy group or an ethoxyethoxy group. R a51 Examples of the alkylcarbonyl group in [[ ]] 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. R a51 Examples of the alkylcarbonyloxy group in [[ ]] 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. R a51 is preferably a halogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, or an alkoxyalkoxy group having 2 to 8 carbon atoms, more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group, or an ethoxymethoxy group, and even more preferably a fluorine atom, an iodine atom, a hydroxy group, a methyl group, a methoxy group, or an ethoxyethoxy group.

[0140] *-X a51 -(A a52 -X a52 ) nb Examples of - include *-O-, *-CO-O-, *-O-CO-, *-CO-O-A a52 -CO-O-, *-O-CO-A a52 -O-, *-O-A a52 -CO-O-, *-CO-O-A a52 -O-CO-, *-O-CO-A a52 -O-CO-, are included. Among them, *-CO-O-, *-CO-O-A a52 -CO-O- or *-O-A a52-CO-O- is preferred.

[0141] Examples of the 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 pentane-1,5-diyl group, a hexane-1,6-diyl group, a butane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, and a 2-methylbutane-1,4-diyl group. A a52 is preferably a methylene group or an ethylene group.

[0142] A a50 is a single bond, *-CO-O- or *-CO-O-A a52 -CO-O- is preferably, more preferably a single bond, *-CO-O- or *-CO-O-CH2-CO-O-, and even more preferably a single bond or *-CO-O-.

[0143] mb is preferably 0, 1 or 2, more preferably 0 or 1, and particularly preferably 0. The hydroxy group is preferably bonded to the ortho position or the para position of the benzene ring, and more preferably bonded to the para position.

[0144] Examples of the structural unit (a2-A) include structural units derived from the monomers described in JP-A-2010-204634 and JP-A-2012-12577. Examples of the structural unit (a2-A) include the structural units represented by formula (a2-2-1) to formula (a2-2-16) and R in the structural unit (a2-A) in the structural units represented by formula (a2-2-1) to formula (a2-2-16). a50Examples of the structural unit include those in which the methyl group corresponding to [[ID=]] is replaced with a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group. The structural unit (a2-A) is the structural unit represented by formula (a2-2-1), the structural unit represented by formula (a2-2-3), the structural unit represented by formula (a2-2-6), the structural unit represented by formula (a2-2-8), the structural units represented by formulas (a2-2-12) to (a2-2-14), and the structural unit represented by formula (a2-2-1), the structural unit represented by formula (a2-2-3), the structural unit represented by formula (a2-2-6), the structural unit represented by formula (a2-2-8), the structural units represented by formulas (a2-2-12) to (a2-2-14), and in the structural unit (a2-A), R a50 is preferably a structural unit in which the methyl group corresponding to [[ID=]] is replaced with a hydrogen atom, and in the structural unit represented by formula (a2-2-3), the structural unit represented by formula (a2-2-8), the structural units represented by formulas (a2-2-12) to (a2-2-14), and the structural unit represented by formula (a2-2-3) or the structural unit represented by formula (a2-2-8), the structural units represented by formulas (a2-2-12) to (a2-2-14), and in the structural unit (a2-A), R a50 is more preferably a structural unit in which the methyl group corresponding to [[ID=]] is replaced with a hydrogen atom, and in the structural unit represented by formula (a2-2-8) and the structural unit represented by formula (a2-2-8), and in the structural unit (a2-A), R a50 is even more preferably a structural unit in which the methyl group corresponding to [[ID=]] is replaced with a hydrogen atom. TIFF0007716229000097.tif63170

[0145] When the resin (A) contains the structural unit (a2-A), the content of the structural unit (a2-A) is preferably 5 to 80 mol%, more preferably 10 to 70 mol%, even more preferably 15 to 65 mol%, and even more preferably 20 to 65 mol% with respect to all the structural units. The structural unit (a2-A) can be incorporated into the resin (A) by, for example, polymerizing using the structural unit (a1-4) and then treating with an acid such as p-toluenesulfonic acid. Also, after polymerizing using acetoxystyrene or the like and then treating with an alkali such as tetramethylammonium hydroxide, the structural unit (a2-A) can be incorporated into the resin (A).

[0146] Examples of the structural unit having an alcoholic hydroxy group in the structural unit (a2) include the structural unit represented by the formula (a2-1) (hereinafter sometimes referred to as "structural unit (a2-1)"). TIFF0007716229000098.tif3853In the formula (a2-1), L a3 represents -O- or *-O-(CH2) k2 -CO-O-, k2 represents an integer of any one of 1 to 7. * represents a bond with -CO-. R a14 represents a hydrogen atom or a methyl group. R a15 and R a16 each independently represent a hydrogen atom, a methyl group or a hydroxy group. o1 represents an integer of any one of 0 to 10.

[0147] In the formula (a2-1), L a3 is preferably -O-, -O-(CH2) f1 -CO-O- (wherein f1 represents an integer of any one of 1 to 4), more preferably -O-. R a14 is preferably a methyl group. R a15 is preferably a hydrogen atom. R a16 is preferably a hydrogen atom or a hydroxy group. o1 is preferably an integer of any one of 0 to 3, more preferably 0 or 1.

[0148] Examples of the structural unit (a2-1) include structural units derived from the monomers described in JP-A-2010-204646. The structural unit represented by any of the formulas (a2-1-1) to (a2-1-6) is preferable, the structural unit represented by any of the formulas (a2-1-1) to (a2-1-4) is more preferable, and the structural unit represented by the formula (a2-1-1) or the formula (a2-1-3) is even more preferable. TIFF0007716229000099.tif54150

[0149] When the resin (A) contains the structural unit (a2-1), the content is usually 1 to 45 mol%, preferably 1 to 40 mol%, more preferably 1 to 35 mol%, even more preferably 1 to 20 mol%, and even more preferably 1 to 10 mol% based on all the structural units of the resin (A).

[0150] 〈Structural unit (a3)〉 The lactone ring of 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, a structural unit represented by the following formula (a3-2)) can be mentioned.

[0151] The structural unit (a3) is preferably a structural unit represented by the formula (a3-1), the formula (a3-2), the formula (a3-3), or the formula (a3-4). These may be contained alone or in combination of two or more. TIFF0007716229000100.tif51163[In the formulas (a3-1), (a3-2), (a3-3), and (a3-4), L a4 , L a5 and L a6 each independently represents a group represented by -O- or *-O-(CH2) k3 -CO-O- (k3 represents an integer of 1 to 7). L a7 is -O-, *-O-La8 -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-. 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 and R a20 each independently represents a hydrogen atom or a methyl group. R a24 represents an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, a hydrogen atom or a halogen atom. X a3 represents -CH2- or an oxygen atom. R a21 represents an aliphatic hydrocarbon group having 1 to 4 carbon atoms. R a22 R a23 and R a25 each independently represents a carboxy group, a cyano group or an aliphatic hydrocarbon group having 1 to 4 carbon atoms. p1 represents any integer from 0 to 5. q1 represents any integer from 0 to 3. r1 represents any integer from 0 to 3. w1 represents any integer from 0 to 8. When p1, q1, r1 and / or w1 is 2 or more, a plurality of R a21 R a22 R a23 and / or R a25 may be the same as or different from each other.

[0152] R a21 R a22 R a23 and R a25Examples of the aliphatic hydrocarbon group in [description] include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, and tert-butyl group. R a24 Examples of the halogen atom in [description] include fluorine atom, chlorine atom, bromine atom, and iodine atom. R a24 Examples of the alkyl group in [description] include methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, and hexyl group, etc. Preferably, alkyl groups having 1 to 4 carbon atoms are included, and more preferably, methyl group or ethyl group is included. R a24 Examples of the alkyl group having a halogen atom in [description] include trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, perfluorosec-butyl group, perfluorotert-butyl group, perfluoropentyl group, perfluorohexyl group, trichloromethyl group, tribromomethyl group, triiodomethyl group, etc. L a8 and L a9 Examples of the alkanediyl group in [description] and [description] include 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, butane-1,3-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, etc.

[0153] In formulas (a3-1) to (a3-3), L a4 ~L a6 are each independently, preferably -O- or, *-O-(CH2) k3 -CO-O- in which k3 is an integer of any one of 1 to 4, more preferably -O- and, *-O-CH2-CO-O-, and even more preferably an oxygen atom. R a18 ~R a21 is preferably a methyl group. R a22 and R a23 are each independently preferably a carboxy group, a cyano group or a methyl group. p1, q1 and r1 are each independently preferably an integer of any one of 0 to 2, more preferably 0 or 1.

[0154] In formula (a3-4), R a24 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or an ethyl group, still more preferably a hydrogen atom or a methyl group. R a25 is preferably a carboxy group, a cyano group or a methyl group. L a7 is preferably -O- or *-O-L a8 -CO-O-, more preferably -O-, -O-CH2-CO-O- or -O-C2H4-CO-O-. w1 is preferably an integer of any one of 0 to 2, more preferably 0 or 1. In particular, formula (a3-4) is preferably formula (a3-4)'. TIFF0007716229000101.tif4051 (wherein R a24 , L a7 represent the same meaning as described above.)

[0155] 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 a18 , R a19 , R a20 and R a24A structural unit in which the methyl group corresponding thereto is replaced by a hydrogen atom is preferred.

[0156] TIFF0007716229000102.tif117165

[0157] When the resin (A) contains the structural unit (a3), the total content is usually 5 to 70 mol%, preferably 10 to 65 mol%, more preferably 10 to 60 mol% with respect to all the structural units of the resin (A). In addition, the content of the structural unit (a3-1), the structural unit (a3-2), the structural unit (a3-3) or the structural unit (a3-4) is preferably 5 to 60 mol%, more preferably 5 to 50 mol%, still more preferably 10 to 50 mol% with respect to all the structural units of the resin (A).

[0158] 〈Structural unit (a4)〉 Examples of the structural unit (a4) include the following structural units. TIFF0007716229000103.tif3066[In the formula (a4), R 41 represents a hydrogen atom or a methyl group. R 42 represents a saturated hydrocarbon group having a fluorine atom with 1 to 24 carbon atoms, and -CH2- contained in the saturated hydrocarbon group may be replaced by -O- or -CO-.] R 42 Examples of the saturated hydrocarbon group represented by include a chain hydrocarbon group, a monocyclic or polycyclic alicyclic hydrocarbon group, and a group formed by combining these.

[0159] Examples of the chain hydrocarbon group include 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. Examples of the monocyclic or polycyclic alicyclic hydrocarbon group include cycloalkyl groups such as cyclopentyl group, cyclohexyl group, cycloheptyl group, and cyclooctyl group; and polycyclic alicyclic hydrocarbon groups such as decahydronaphthyl group, adamantyl group, norbornyl group, and the following group (* represents a bond). TIFF0007716229000104.tif11159Examples of the group formed by the combination include a group formed by combining one or more alkyl groups or one or more alkanediyl groups with one or more alicyclic hydrocarbon groups, such as -alkanediyl group-alicyclic hydrocarbon group, -alicyclic hydrocarbon group-alkyl group, -alkanediyl group-alicyclic hydrocarbon group-alkyl group, and the like.

[0160] Examples of the structural unit (a4) include a structural unit represented by at least one selected from the group consisting of formula (a4-0), formula (a4-1), formula (a4-2), formula (a4-3), and formula (a4-4). TIFF0007716229000105.tif4652[In formula (a4-0), R 5 represents a hydrogen atom or a methyl group. L 4a represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 4 carbon atoms. L 3a represents a perfluoroalkanediyl group having 1 to 8 carbon atoms or a perfluorocycloalkanediyl group having 3 to 12 carbon atoms. R 6 represents a hydrogen atom or a fluorine atom.]

[0161] L 4aExamples of the divalent aliphatic saturated hydrocarbon group in [substance] include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, etc., and branched alkanediyl groups such as ethane-1,1-diyl group, propane-1,2-diyl group, butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, and 2-methylpropane-1,2-diyl group. L 3a Examples of the perfluoroalkanediyl group in [substance] include difluoromethylene group, perfluoroethylene group, perfluoropropane-1,1-diyl 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, etc. L 3a Examples of the perfluorocycloalkanediyl group in [substance] include perfluorocyclohexanediyl group, perfluorocyclopentanediyl group, perfluorocycloheptanediyl group, perfluoroadamantanediyl group, etc.

[0162] L 4a is preferably a single bond, a methylene group or an ethylene group, and more preferably a single bond or a methylene group. L 3a is preferably a perfluoroalkanediyl group having 1 to 6 carbon atoms, and more preferably a perfluoroalkanediyl group having 1 to 3 carbon atoms.

[0163] As the structural unit (a4-0), there are the following structural units and the structural units in the following structural units where the methyl group corresponding to R in the structural unit (a4-0) is replaced by a hydrogen atom. 5 Examples include structural units in which the methyl group corresponding to R is replaced by a hydrogen atom. TIFF0007716229000106.tif98165

[0164] TIFF0007716229000107.tif4466[In formula (a4-1), R a41 represents a hydrogen atom or a methyl group. R a42 represents a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the saturated hydrocarbon group may be replaced by -O- or -CO-. A a41 represents an alkanediyl group having 1 to 6 carbon atoms which may have a substituent or a group represented by formula (a-g1). However, at least one of a41 A a42 and R has a halogen atom (preferably a fluorine atom) as a substituent. TIFF0007716229000108.tif1384[In formula (a-g1), s represents 0 or 1. A a42 and A a44 each independently represent a divalent saturated hydrocarbon group having 1 to 5 carbon atoms which may have a substituent. A a43 represents a single bond or a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms which may have a substituent. X a41 and X a42 each independently represent -O-, -CO-, -CO-O- or -O-CO-. However, the total number of carbon atoms of a42 A a43 A a44 X a41 and X a42 is 7 or less. ] * represents a bond, and the * on the right side is -O-CO-Ra42 is a bonding hand with respect to.]

[0165] R a42 Examples of the saturated hydrocarbon group in R include a chain saturated hydrocarbon group, a monocyclic or polycyclic alicyclic saturated hydrocarbon group, and a group formed by combining these. Examples of the chain saturated hydrocarbon 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, a decyl group, a dodecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, and an octadecyl group. Examples of the monocyclic or polycyclic alicyclic hydrocarbon group include cycloalkyl groups such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group; polycyclic alicyclic saturated hydrocarbon groups such as a decahydronaphthyl group, an adamantyl group, a norbornyl group, and the following group (* represents a bonding hand). Examples of the group formed by combination include a group 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, etc.

[0166] R a42 Examples of the substituent that R may have include at least one selected from a halogen atom and a group represented by the formula (a-g3). Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and preferably a fluorine atom. TIFF0007716229000110.tif965[In the formula (a-g3), X a43 represents an oxygen atom, a carbonyl group, *-O-CO- or *-CO-O-. A a45 represents an aliphatic hydrocarbon group having 1 to 17 carbon atoms which may have a halogen atom. * is a bonding hand with respect to R a42 and represents.] However, Ra42 -X a43 -A a45 In, when R a42 has no halogen atom, A a45 represents an aliphatic hydrocarbon group having 1 to 17 carbon atoms and at least one halogen atom.

[0167] A a45 Examples of the aliphatic hydrocarbon group in A include 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; monocyclic alicyclic hydrocarbon groups such as cyclopentyl group, cyclohexyl group, cycloheptyl group, and cyclooctyl group; and polycyclic alicyclic hydrocarbon groups such as decahydronaphthyl group, adamantyl group, norbornyl group, and the following group (* represents a bond). Examples of the group formed by the combination of TIFF0007716229000111.tif11159 include groups formed by combining one or more alkyl groups or one or more alkanediyl groups with one or more alicyclic hydrocarbon groups, such as -alkanediyl group-alicyclic hydrocarbon group, -alicyclic hydrocarbon group-alkyl group, -alkanediyl group-alicyclic hydrocarbon group-alkyl group, etc.

[0168] R a42 is preferably an aliphatic hydrocarbon group which may have a halogen atom, more preferably an alkyl group having a halogen atom and / or an aliphatic hydrocarbon group having a group represented by the formula (a-g3). R a42When it is an aliphatic hydrocarbon group having a halogen atom, it is preferably an aliphatic hydrocarbon group having a fluorine atom, more preferably a perfluoroalkyl group or a perfluorocycloalkyl group, still more preferably a perfluoroalkyl group having 1 to 6 carbon atoms, and particularly preferably a perfluoroalkyl group having 1 to 3 carbon atoms. Examples of the perfluoroalkyl group include a perfluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a perfluoroheptyl group, and a perfluorooctyl group. Examples of the perfluorocycloalkyl group include a perfluorocyclohexyl group. R a42 When R is an aliphatic hydrocarbon group having a group represented by the formula (a-g3), including the number of carbon atoms contained in the group represented by the formula (a-g3), R a42 Preferably has a total carbon number of 15 or less, more preferably 12 or less. When having a group represented by the formula (a-g3) as a substituent, the number thereof is preferably 1.

[0169] R a42 When R is an aliphatic hydrocarbon having a group represented by the formula (a-g3), R a42 Is more preferably a group represented by the formula (a-g2). TIFF0007716229000112.tif879 [In the formula (a-g2), A a46 Represents a divalent aliphatic hydrocarbon group having 1 to 17 carbon atoms which may have a halogen atom. X a44 Represents -O-CO- or -CO-O- (** represents the bond to A a46 ). A a47 Represents an aliphatic hydrocarbon group having 1 to 17 carbon atoms which may have a halogen atom. However, A a46 、A a47 And X a44 The total number of carbon atoms of is 18 or less, and A a46 And A a47 At least one of them has at least one halogen atom. * represents a bond to a carbonyl group.

[0170] A a46 The aliphatic hydrocarbon group of A preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms. A a47 The aliphatic hydrocarbon group of A preferably has 4 to 15 carbon atoms, more preferably 5 to 12 carbon atoms, and A a47 is more preferably a cyclohexyl group or an adamantyl group.

[0171] The preferred structure of the group represented by formula (a-g2) is the following structure (* is a bond to a carbonyl group). TIFF0007716229000113.tif13161

[0172] A a41 Examples of the alkanediyl group in A 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. A a41 Examples of the substituent in the alkanediyl group of A include a hydroxy group and an alkoxy group having 1 to 6 carbon atoms. A a41 is preferably an alkanediyl group having 1 to 4 carbon atoms, more preferably an alkanediyl group having 2 to 4 carbon atoms, and even more preferably an ethylene group.

[0173] A in the group represented by formula (a-g1) a42 、A a43 and A a44Examples of the divalent saturated hydrocarbon group represented by include a linear or branched alkanediyl group, a monocyclic divalent alicyclic hydrocarbon group, and a group formed by combining an alkanediyl group and a divalent alicyclic hydrocarbon group. Specific examples include a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a 1-methylpropane-1,3-diyl group, a 2-methylpropane-1,3-diyl group, and a 2-methylpropane-1,2-diyl group. A a42 , A a43 and A a44 Examples of the substituent of the divalent saturated hydrocarbon group represented by the formula include a hydroxy group and an alkoxy group having 1 to 6 carbon atoms. Preferably, s is 0.

[0174] In the group represented by formula (a-g1), X a42 In the following examples, * and ** each represent a bond, and ** represents -O-CO-R a42 It is a combination of. TIFF0007716229000114.tif54162

[0175] The structural unit represented by formula (a4-1) includes the structural units shown below and R in the structural unit represented by formula (a4-1) in the structural units shown below. a41 The structural unit in which a methyl group corresponding to the above is replaced with a hydrogen atom is an example. TIFF0007716229000115.tif167144

[0176] TIFF0007716229000116.tif66133

[0177] The structural unit represented by formula (a4-1) is preferably a structural unit represented by formula (a4-2). TIFF0007716229000117.tif4365[In formula (a4-2), R f5represents a hydrogen atom or a methyl group. L 44 represents an alkanediyl group having 1 to 6 carbon atoms, and -CH2- contained in the alkanediyl group may be replaced by -O- or -CO-. R f6 represents a saturated hydrocarbon group having 1 to 20 carbon atoms and having a fluorine atom. However, L 44 and R f6 The upper limit of the total number of carbon atoms is 21.

[0178] L 44 The alkanediyl group having 1 to 6 carbon atoms of L a41 includes the same groups as those exemplified for the alkanediyl group in A R f6 The saturated hydrocarbon group of R a42 includes the same groups as those exemplified for R L 44 As the alkanediyl group having 1 to 6 carbon atoms in L

[0179] Examples of the structural unit represented by the formula (a4-2) include, for example, the structural units represented by the formulas (a4-1-1) to (a4-1-11). The structural unit in which the methyl group corresponding to R f5 in the structural unit (a4-2) is replaced by a hydrogen atom is also included as the structural unit represented by the formula (a4-2).

[0180] Examples of the structural unit (a4) include the structural unit represented by the formula (a4-3). TIFF0007716229000118.tif5771[In the formula (a4-3), R f7 represents a hydrogen atom or a methyl group. L 5 represents an alkanediyl group having 1 to 6 carbon atoms. A f13 represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms which may have a fluorine atom. X f12represents *-O-CO- or *-CO-O- (* represents a bond with A f13 .). A f14 represents a saturated hydrocarbon group having 1 to 17 carbon atoms which may have a fluorine atom. However, at least one of A f13 and A f14 has a fluorine atom, and the upper limit of the total carbon number of L 5 , A f13 and A f14 is 20.]

[0181] L 5 As the alkanediyl group in, groups similar to those exemplified as the alkanediyl group in the divalent saturated hydrocarbon group of A a41 can be mentioned. A f13 The divalent saturated hydrocarbon group which may have a fluorine atom in is preferably a divalent aliphatic saturated hydrocarbon group which may have a fluorine atom and a divalent alicyclic saturated hydrocarbon group which may have a fluorine atom, and more preferably a perfluoroalkanediyl group. Examples of the divalent aliphatic hydrocarbon group which may have a fluorine atom include alkanediyl groups such as a methylene group, an ethylene group, a propanediyl group, a butanediyl group and a pentanediyl group; perfluoroalkanediyl groups such as a difluoromethylene group, a perfluoroethylene group, a perfluoropropanediyl group, a perfluorobutanediyl group and a perfluoropentanediyl group. The divalent alicyclic hydrocarbon group which may have a fluorine atom may be either monocyclic or polycyclic. Examples of the monocyclic group include a cyclohexanediyl group and a perfluorocyclohexanediyl group. Examples of the polycyclic group include an adamantanediyl group, a norbornanediyl group, a perfluoroadamantanediyl group. A f14 The saturated hydrocarbon group and the saturated hydrocarbon group which may have a fluorine atom of are R a42Groups similar to those exemplified above can be mentioned. Among them, alkyl fluoride groups such as 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, heptyl group, perfluoroheptyl group, octyl group and perfluorooctyl group, cyclopropylmethyl group, cyclopropyl group, cyclobutylmethyl group, cyclopentyl group, cyclohexyl group, perfluorocyclohexyl group, adamantyl group, adamantylmethyl group, adamantyldimethyl group, norbornyl group, norbornylmethyl group, perfluoroadamantyl group, perfluoroadamantylmethyl group, etc. are preferable.

[0182] In formula (a4-3), L 5 is preferably an ethylene group. A f13 The divalent saturated hydrocarbon group of is preferably a group containing a divalent chain hydrocarbon group having 1 to 6 carbon atoms and a divalent alicyclic hydrocarbon group having 3 to 12 carbon atoms, and more preferably a divalent chain hydrocarbon group having 2 to 3 carbon atoms. A f14 The saturated hydrocarbon group of is preferably a group containing a chain hydrocarbon group having 3 to 12 carbon atoms and an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and more preferably a group containing a chain hydrocarbon group having 3 to 10 carbon atoms and an alicyclic hydrocarbon group having 3 to 10 carbon atoms. Among them, A f14 is preferably a group containing an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and more preferably a cyclopropylmethyl group, a cyclopentyl group, a cyclohexyl group, a norbornyl group and an adamantyl group.

[0183] Examples of the structural unit represented by formula (a4-3) include structural units represented by formulas (a4-1'-1) to (a4-1'-11), respectively. R in structural unit (a4-3)f7 A structural unit in which the methyl group corresponding to

[0184] Examples of the structural unit (a4) include a structural unit represented by the formula (a4-4). TIFF0007716229000119.tif4466[In the formula (a4-4), R f21 represents a hydrogen atom or a methyl group. A f21 represents -(CH2) j1 -, -(CH2) j2 -O-(CH2) j3 - or -(CH2) j4 -CO-O-(CH2) j5 -. j1 to j5 each independently represent an integer from 1 to 6. R f22 represents a saturated hydrocarbon group having 1 to 10 carbon atoms and having a fluorine atom.]

[0185] R f22 The saturated hydrocarbon group of a42 is the same as the saturated hydrocarbon group represented by R f22 R preferably represents an alkyl group having 1 to 10 carbon atoms and having a fluorine atom or an alicyclic 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, and even more preferably an alkyl group having 1 to 6 carbon atoms and having a fluorine atom.

[0186] In the formula (a4-4), A f21 is preferably -(CH2) j1 -, more preferably an ethylene group or a methylene group, and even more preferably a methylene group.

[0187] Examples of the structural unit represented by the formula (a4-4) include, for example, the following structural units and structural units represented by the following formulas, in which the methyl group corresponding to R f21 in the structural unit (a4-4) is replaced by a hydrogen atom. TIFF0007716229000120.tif80148

[0188] When the resin (A) has the structural unit (a4), its content is preferably 1 to 20 mol%, more preferably 2 to 15 mol%, and still more preferably 3 to 10 mol% based on all the structural units of the resin (A).

[0189] 〈Structural unit (a5)〉 Examples of the non-leaving hydrocarbon group contained in 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. Examples of the structural unit (a5) include a structural unit represented by the formula (a5-1). TIFF0007716229000121.tif3971[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. L 55 represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the saturated hydrocarbon group may be replaced by -O- or -CO-.]

[0190] R 52 The alicyclic hydrocarbon group in 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. 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. 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. L 55 Examples of the divalent saturated hydrocarbon group in L 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 propanediyl group, a butanediyl group and a pentanediyl group. 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 cyclopentanediyl group and a cyclohexanediyl group. Examples of the polycyclic divalent alicyclic saturated hydrocarbon group include an adamantanediyl group and a norbornanediyl group.

[0191] L 55 Examples of the group in which -CH2- contained in the divalent saturated hydrocarbon group represented by L is replaced with -O- or -CO- include the groups represented by formula (L1-1) to formula (L1-4). In the following formulas, * and ** each represent a bond, and * represents a bond to an oxygen atom. In formula (L1-1), X x1 represents *-O-CO- or *-CO-O- (* represents a bond to L x1 .). 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. In formula (L1-2), Lx3 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. However, for L x3 and L x4 the total number of carbon atoms is 17 or less. In formula (L1-3), L x5 represents a divalent aliphatic saturated hydrocarbon group having 1 to 15 carbon atoms. L x6 and L x7 each independently represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 14 carbon atoms. However, for L x5 L x6 and L x7 the total number of carbon atoms is 15 or less. In formula (L1-4), L x8 and L x9 each represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 12 carbon atoms. W x1 represents a divalent alicyclic saturated hydrocarbon group having 3 to 15 carbon atoms. However, for L x8 L x9 and W x1 the total number of carbon atoms is 15 or less.

[0192] 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. 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. [[ID=6)7]]L x4 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x5is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably a methylene group or an ethylene group. 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. 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. 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.

[0193] Examples of the group represented by the formula (L1-1) include the following divalent groups. TIFF0007716229000123.tif23135

[0194] TIFF0007716229000124.tif54134

[0195] Examples of the group represented by the formula (L1-2) include the following divalent groups. TIFF0007716229000125.tif23130

[0196] Examples of the group represented by the formula (L1-3) include the following divalent groups. TIFF0007716229000126.tif15145

[0197] Examples of the group represented by the formula (L1-4) include the following divalent groups. TIFF0007716229000127.tif26114

[0198] L 55 is preferably a single bond or a group represented by the formula (L1-1).

[0199] Examples of the structural unit (a5-1) include the following structural units and the structural units in the following structural units where the methyl group corresponding to R 51 in the structural unit (a5-1) is replaced by a hydrogen atom. TIFF0007716229000128.tif75150

[0200] When the resin (A) has 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% based on all the structural units of the resin (A).

[0201] 〈Structural unit (a6)〉 The structural unit (a6) is a structural unit having a -SO2- group, and preferably has a -SO2- group in the side chain. The structural unit having a -SO2- group may have a linear structure having a -SO2- group, a branched structure having a -SO2- group, or a cyclic structure (monocyclic and polycyclic structures) having a -SO2- group. Preferably, it is a structural unit having a cyclic structure having a -SO2- group, and more preferably, it is a structural unit having a cyclic structure containing -SO2-O- (sultone ring).

[0202] 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 -SO2-O- as an atomic group constituting the ring, and the formula (T 1-1) and formula (T 1 -2). Examples of the sultone ring include the ring represented by formula (T 1 -2). Like the ring represented by formula (T TIFF0007716229000130.tif3187

[0203] The sultone ring may have a substituent. 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.

[0204] 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. 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 mentioned. 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. Examples of the aryl group include a phenyl group, naphthyl group, anthryl group, p-methylphenyl group, p-tert-butylphenyl group, p-adamantylphenyl group, tolyl group, xylyl group, cumyl group, mesityl group, biphenyl group, phenanthryl group, 2,6-diethylphenyl group, and 2-methyl-6-ethylphenyl group. Examples of the aralkyl group include a benzyl group, phenethyl group, phenylpropyl group, naphthylmethyl group, and naphthylethyl group. Examples of the alkoxycarbonyl group include a group in which an alkoxy group such as a methoxycarbonyl group or an ethoxycarbonyl group is bonded to a carbonyl group, preferably an alkoxycarbonyl group having 6 or less carbon atoms, and more preferably a methoxycarbonyl group. Examples of the alkylcarbonyl group include an acetyl group, propionyl group, and butyryl group.

[0205] From the viewpoint of easy production of the monomer leading to the structural unit (a6), a sultone ring having no substituent is preferred. As the sultone ring, a ring represented by the following formula (T1') is preferred. TIFF0007716229000131.tif3172[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. 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, and more preferably a methylene group. R 41 Examples thereof include the same as the substituents 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 preferable.

[0206] As the sultone ring, a ring represented by the formula (T1) is more preferable. TIFF0007716229000132.tif3149[In the formula (T1), R 8 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. m represents any integer from 0 to 9. When m is 2 or more, a plurality of R 8 may be the same or different. The bonding site is at an arbitrary position.]

[0207] R 8 is the same as R 41 Examples thereof include the same as those of. ma in the formula (T1') and m in the formula (T1) are preferably 0 or 1, and more preferably 0.

[0208] Examples of the ring represented by the formula (T1') and the ring represented by the formula (T1) include the following rings. The bonding site is at an arbitrary position. TIFF0007716229000133.tif52157

[0209] The structural unit having a sultone ring preferably has the following group. * in the following group represents the bonding site. TIFF0007716229000134.tif50160

[0210] The structural unit having a -SO2- 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. Among them, the monomer that leads to the structural unit (a6) is preferably a monomer having an ethylenically unsaturated bond, more preferably a (meth)acrylic monomer.

[0211] The structural unit (a6) is preferably a structural unit represented by the formula (Ix). TIFF0007716229000135.tif4956[In the formula (Ix), 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 xx represents an oxygen atom, -N(R c )- or a sulfur atom. A x represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the saturated hydrocarbon group may be replaced by -O-, -CO- or -N(R d )-. 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. 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.]

[0212] R x Examples of the halogen atom of R include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. 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. 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. R x R 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.

[0213] 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 those obtained by combining two or more of these groups may also be used. 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. may be mentioned.

[0214] R 41 、X 11 And ma are the same as those in formula (T1’). Examples of the sultone ring include those described above, and among them, those with specific bonding positions are preferred.

[0215] Examples of the structural unit (a6) include the following structural units. TIFF0007716229000136.tif99158

[0216] 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. When the resin (A) has 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).

[0217] <Structural unit (II)> The resin (A) may further contain a structural unit that decomposes upon exposure to generate an acid (hereinafter sometimes referred to as "structural unit (II)"). Specific examples of the structural unit (II) include the structural units described in JP-A-2016-79235, and 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 is preferred.

[0218] The structural unit having a sulfonate group or a carboxylate group in the side chain is preferably a structural unit represented by formula (II-2-A'). TIFF0007716229000137.tif35104 [In formula (II-2-A'), X III3 represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and -CH2- contained in the saturated hydrocarbon group may be replaced by -O-, -S- or -CO-, and a hydrogen atom contained in the saturated hydrocarbon group may be replaced by a halogen atom, an alkyl group having 1 to 6 carbon atoms which may have a halogen atom or a hydroxy group. A x1 represents an alkanediyl group having 1 to 8 carbon atoms, and a hydrogen atom contained in the alkanediyl group may be substituted by a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms. RA - represents a sulfonate group or a carboxylate group. R III3represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. ZA + represents an organic cation.

[0219] R III3 Examples of the halogen atom represented by R include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, and the like. R III3 Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom represented by R include the same ones as the alkyl group having 1 to 6 carbon atoms which may have a halogen atom represented by R. a8 Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom represented by R include the same ones as the alkyl group having 1 to 6 carbon atoms which may have a halogen atom represented by R. A x1 Examples of the alkanediyl group having 1 to 8 carbon atoms represented by A include a methylene group, an ethylene group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, a hexane-1,6-diyl group, an ethane-1,1-diyl group, a propane-1,1-diyl group, a propane-1,2-diyl group, a propane-2,2-diyl group, a pentane-2,4-diyl group, a 2-methylpropane-1,3-diyl group, a 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group, a 2-methylbutane-1,4-diyl group, and the like. A X1 Examples of the perfluoroalkyl group having 1 to 6 carbon atoms which may be substituted in A 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, and the like. X III3 Examples of the divalent saturated hydrocarbon group having 1 to 18 carbon atoms represented by X include a linear or branched alkanediyl group, a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, and combinations thereof may also be possible. 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; 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 such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, adamantane-2,6-diyl group, etc. may be mentioned. Examples of those in which -CH2- contained in the saturated hydrocarbon group is replaced by -O-, -S- or -CO- include divalent groups represented by formula (X1) to formula (X53). However, the number of carbon atoms before -CH2- contained in the saturated hydrocarbon group is replaced by -O-, -S- or -CO- is 17 or less, respectively. In the following formulae, * and ** represent bonding sites, and * represents a bond to A x1 and represents a bond to A. TIFF0007716229000138.tif145161

[0220] 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. 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 8represents a divalent saturated hydrocarbon group having 1 to 13 carbon atoms.

[0221] ZA in formula (II-2-A’) + is the same as the cation Z1 in the salt represented by formula (B1). + Examples thereof include the same ones.

[0222] The structural unit represented by formula (II-2-A’) is preferably the structural unit represented by formula (II-2-A). TIFF0007716229000139.tif38109[In formula (II-2-A), R III3 , X III3 and ZA + represent the same meanings as described above. z2A represents any integer from 0 to 6. R III2 and R III4 each independently represent a hydrogen atom, a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms. When z2A is 2 or more, a plurality of R III2 and R III4 may be the same as or different from each other. Q a and Q b each independently represent a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms.] R III2 , R III4 , Q a and Q b Examples of the perfluoroalkyl group having 1 to 6 carbon atoms represented by b1 are the same as those of the perfluoroalkyl group having 1 to 6 carbon atoms represented by the aforementioned Q.

[0223] The structural unit represented by formula (II-2-A) is preferably the structural unit represented by formula (II-2-A-1). TIFF0007716229000140.tif5577[In formula (II-2-A-1), R III2 , R III3 , R III4 , Q a , Qb and ZA + represents the same meaning as described above. R III5 represents a saturated hydrocarbon group having 1 to 12 carbon atoms. z2A1 represents any integer from 0 to 6. X I2 represents a divalent saturated hydrocarbon group having 1 to 11 carbon atoms, wherein -CH2- contained in the saturated hydrocarbon group may be replaced by -O-, -S- or -CO-, and a hydrogen atom contained in the saturated hydrocarbon group may be replaced by a halogen atom or a hydroxy group. R III5 Examples of the saturated hydrocarbon group having 1 to 12 carbon atoms represented by R include linear or branched alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group and dodecyl group. X I2 Examples of the divalent saturated hydrocarbon group represented by X include those similar to the divalent saturated hydrocarbon group represented by X III3 represented by.

[0224] As the structural unit represented by the formula (II-2-A-1), the structural unit represented by the formula (II-2-A-2) is more preferable. TIFF0007716229000141.tif5287 [In the formula (II-2-A-2), R III3 R III5 and ZA + represent the same meaning as described above. m and nA each independently represent 1 or 2.

[0225] Examples of the structural unit represented by the formula (II-2-A') include, for example, the following structural units, R III3 a group corresponding to the methyl group of which 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 WO 2012 / 050015. ZA+ represents an organic cation. TIFF0007716229000142.tif86163

[0226] The structural unit having a sulfonio group and an organic anion in the side chain is preferably a structural unit represented by the formula (II-1-1). TIFF0007716229000143.tif3791[In the formula (II-1-1), A II1 represents a single bond or a divalent linking group. R II1 represents a divalent aromatic hydrocarbon group having 6 to 18 carbon atoms. R II2 and R II3 each independently represent a hydrocarbon group having 1 to 18 carbon atoms, and R II2 and R II3 may combine with each other to form a ring together with the sulfur atom to which they are attached. R II4 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. A - represents an organic anion.] R II1 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 II2 and R II3 Examples of the hydrocarbon group represented by include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, and a group formed by combining these. R II4 Examples of the halogen atom represented by R include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. R II4 Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom represented by R are the same as those of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom represented by R a8 . A II1Examples of the divalent linking group represented by include divalent saturated hydrocarbon groups having 1 to 18 carbon atoms, and the -CH2- contained in the divalent saturated hydrocarbon group may be replaced by -O-, -S- or -CO-. Specifically, X III3 include the same divalent saturated hydrocarbon groups having 1 to 18 carbon atoms as those represented by .

[0227] Examples of the structural unit containing the cation in formula (II-1-1) include the structural unit represented by the following and the group corresponding to the methyl group of R II4 structural units in which the group corresponding to the methyl group of is replaced by a hydrogen atom, a fluorine atom, a trifluoromethyl group, etc. TIFF0007716229000144.tif84130

[0228] A - Examples of the organic anion represented by include sulfonate anions, sulfonylimide anions, sulfonylmethide anions, carboxylic acid anions, etc. A - The organic anion represented by is preferably a sulfonate anion, and more preferably an anion contained in the salt represented by the aforementioned formula (B1). The sulfonylimide anion, sulfonylmethide anion and carboxylic acid anion are more preferably the anion AI - contained in the salt represented by the aforementioned formula (I).

[0229] Examples of the structural unit represented by formula (II-1-1) include the structural unit represented by the following, etc. TIFF0007716229000145.tif88149

[0230] When the resin (A) contains the structural unit (II), the content of the structural unit (II) is preferably 1 to 20 mol%, more preferably 2 to 15 mol%, and still more preferably 3 to 10 mol% based on all the structural units of the resin (A).

[0231] Resin (A) may have structural units other than the above-described structural units, and examples of such structural units include structural units well-known in the art.

[0232] Resin (A) is preferably a resin composed of structural unit (a1) and structural unit (s), that is, a copolymer of monomer (a1) and monomer (s). Structural unit (a1) is preferably at least one selected from the group consisting of structural unit (a1-0), structural unit (a1-1), and structural unit (a1-2) (preferably the structural unit having a cyclohexyl group and a cyclopentyl group), more preferably at least two kinds, and still more preferably at least two kinds selected from the group consisting of structural unit (a1-1) and structural unit (a1-2). Structural unit (s) is preferably at least one selected from the group consisting of structural unit (a2) and structural unit (a3). Structural unit (a2) is preferably structural unit (a2-1) or structural unit (a2-A). Structural unit (a3) is preferably at least one selected from the group consisting of the structural unit represented by formula (a3-1), the structural unit represented by formula (a3-2), and the structural unit represented by formula (a3-4). Each structural unit constituting 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 leading to these structural units. The content ratio of each structural unit possessed by resin (A) can be adjusted by the amount of monomers used in the polymerization. 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). In this specification, the weight average molecular weight is a value determined under the conditions described in the examples by gel permeation chromatography.

[0233] <Resin other than resin (A)> The resist composition of the present invention may be used in combination with a resin other than resin (A). Examples of the resin other than the resin (A) include a resin containing a structural unit (a4) or a structural unit (a5) (hereinafter sometimes referred to as resin (X)). Among them, the resin containing the structural unit (a4) is preferred as the resin (X). In the resin (X), the content of the structural unit (a4) is preferably 30 mol% or more, more preferably 40 mol% or more, and even more preferably 45 mol% or more based on the total of all the structural units of the resin (X). Examples of the structural unit that the resin (X) may further have include a structural unit (a1), a structural unit (a2), a structural unit (a3), and a 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). 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 the monomers used in the polymerization. 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). The measuring means of the weight average molecular weight of the resin (X) is the same as that of the resin (A).

[0234] 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, even more preferably 1 to 40 parts by mass, still more preferably 1 to 30 parts by mass, and particularly preferably 1 to 8 parts by mass with respect to 100 parts by mass of the resin (A).

[0235] The content rate of the resin (A) in the resist composition is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, based on the solid content of the resist composition. When a resin other than the resin (A) is included, the total content rate of the resin (A) and the resin other than the resin (A) is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, based on the solid content of the resist composition. 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. The solid content of the resist composition and the content rate of the resin with respect thereto can be measured by known analysis means such as liquid chromatography or gas chromatography.

[0236] <solvent (E)> The content rate of the solvent (E) in the resist composition is usually 90% by mass or more and 99.9% by mass or less, preferably 92% by mass or more and 99% by mass or less, more preferably 94% by mass or more and 99% by mass or less. The content rate of the solvent (E) can be measured by known analysis means such as liquid chromatography or gas chromatography.

[0237] Examples of the solvent (E) include glycol ether esters such as ethyl cellosolve acetate, methyl cellosolve acetate, and propylene glycol monomethyl ether acetate; glycol ethers such as propylene glycol monomethyl ether; esters such as ethyl lactate, butyl acetate, amyl acetate, and ethyl pyruvate; ketones such as acetone, methyl isobutyl ketone, 2-heptanone, and cyclohexanone; cyclic esters such as γ-butyrolactone; and the like. One kind of the solvent (E) may be used alone, or two or more kinds may be used.

[0238] <quencher (C)> Examples of the quencher (C) include salts that generate an acid having a lower acidity than the acid generated from the basic nitrogen-containing organic compound and the acid generator (B). When the resist composition contains the quencher (C), the content of the quencher (C) is preferably about 0.01 to 15% by mass, more preferably about 0.01 to 10% by mass, still more preferably about 0.1 to 5% by mass, and even more preferably about 0.1 to 3% by mass, based on the solid content of the resist composition. Examples of the basic nitrogen-containing organic compound include amines and ammonium salts. Examples of the amine include aliphatic amines and aromatic amines. Examples of the aliphatic amine include primary amines, secondary amines, and tertiary amines.

[0239] Examples of the amine include 1-naphthylamine, 2-naphthylamine, aniline, diisopropyl aniline, 2-, 3- or 4-methyl aniline, 4-nitroaniline, N-methylaniline, N,N-dimethylaniline, diphenylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, dibutylamine, dipentylamine, dihexylamine, diheptylamine, dioctylamine, dinonylamine, didecylamine, triethylamine, trimethylamine, tripropylamine, tributylamine, tripentylamine, trihexylamine, triheptylamine, trioctylamine, trinonylamine, tridecylamine, methyldibutylamine, methyldipentylamine, methyldihexylamine, methyldicyclohexylamine, methyldiheptylamine, methyldioctylamine, methyldinonylamine, methyldidecylamine, ethyldibutylamine, ethyldipentylamine, ethyldihexylamine, ethyldiheptylamine, ethyldioctylamine, ethyldinonylamine, ethyldidecylamine, dicyclohexylmethylamine, tris[2-(2-methoxyethoxy)ethyl]amine, triisopropanolamine, ethylenediamine, tetramethylenediamine, hexamethylenediamine, 4,4'-diamino-1,2-diphenylethane, 4,4'-diamino-3,3'-dimethyldiphenylmethane, 4,4'-diamino-3,3'-diethyldiphenylmethane, 2,2'-methylenebisaniline, imidazole, 4-methylimidazole, pyridine, 4-methylpyridine, 1,2-di(2-pyridyl)ethane, 1,2-di(4-pyridyl)ethane, 1,2-di(2-pyridyl)ethene, 1,2-di(4-pyridyl)ethene, 1,3-di(4-pyridyl)propane, 1,2-di(4-pyridyloxy)ethane, di(2-pyridyl)ketone, 4,4'-dipyridylsulfide, 4,4'-dipyridyldisulfide, 2,2'-dipyridylamine, 2,2'-dipicolylamine, bipyridine, etc. Preferably, diisopropyl aniline is mentioned, and more preferably 2,6-diisopropyl aniline is mentioned.

[0240] Examples of the ammonium salt include tetramethylammonium hydroxide, tetraisopropylammonium hydroxide, tetrabutylammonium hydroxide, tetrahexylammonium hydroxide, tetraoctylammonium hydroxide, phenyltrimethylammonium hydroxide, 3-(trifluoromethyl)phenyltrimethylammonium hydroxide, tetra-n-butylammonium salicylate, choline, and the like.

[0241] The acidity of a salt that generates an acid with a lower acidity than the acid generated from the acid generator (B) is represented by the acid dissociation constant (pKa). A salt that generates an acid with a lower acidity than the acid generated from the acid generator (B) is a salt in which the acid dissociation constant of the acid generated from the salt is usually a salt with -3 < pKa, preferably a salt with -1 < pKa < 7, and more preferably a salt with 0 < pKa < 5. Examples of the salt that generates an acid with a lower acidity than the acid generated from the acid generator (B) include salts represented by the following formula, salts represented by formula (D) described in JP-A-2015-147926 (hereinafter sometimes referred to as "weak acid inner salt (D)"), and salts described in JP-A-2012-229206, JP-A-2012-6908, JP-A-2012-72109, JP-A-2011-39502, and JP-A-2011-191745. The salt that generates an acid with a lower acidity than the acid generated from the acid generator (B) is preferably a salt that generates a carboxylic acid with a lower acidity than the acid generated from the acid generator (B) (a salt having a carboxylic acid anion), and more preferably a weak acid inner salt (D). TIFF0007716229000146.tif94163

[0242] Examples of the weak acid inner salt (D) include the following salts. TIFF0007716229000147.tif72165

[0243] 〈Other components〉 The resist composition of the present invention may contain, if necessary, components other than the above-described components (hereinafter sometimes referred to as "other components (F)"). There is no particular limitation on the other components (F), and additives known in the resist field, such as sensitizers, dissolution inhibitors, surfactants, stabilizers, dyes, etc. can be used.

[0244] 〈Preparation of Resist Composition〉 The resist composition of the present invention can be prepared by mixing salt (I), resin (A) and acid generator (B), and, if necessary, a resin other than the resin (A) used, solvent (E), quencher (C) and other components (F). The mixing order is arbitrary and not particularly limited. The temperature during mixing can be appropriately selected from 10 to 40°C according to the type of resin, etc. and the solubility of the resin, etc. in the solvent (E). The mixing time can be appropriately selected from 0.5 to 24 hours according to the mixing temperature. Note that the mixing means is also not particularly limited, and stirring and mixing, etc. can be used. After mixing the respective components, it is preferable to filter using a filter having a pore size of about 0.003 to 0.2 μm.

[0245] 〈Method for Manufacturing Resist Pattern〉 The method for manufacturing a resist pattern of the present invention (1) A step of applying the resist composition of the present invention onto a substrate, (2) A step of drying the applied composition to form a composition layer, (3) A step of exposing the composition layer, (4) A step of heating the exposed composition layer, and (5) A step of developing the heated composition layer. To apply the resist composition onto a substrate, it can be carried out by a commonly used apparatus such as a spin coater. Examples of the substrate include inorganic substrates such as silicon wafers. Before applying the resist composition, the substrate may be cleaned, or an antireflection film, etc. may be formed on the substrate. By drying the composition after coating, the solvent is removed to form a composition layer. Drying is performed, for example, by evaporating the solvent using a heating device such as a hot plate (so-called pre-baking), or by using a decompression device. The heating temperature is preferably 50 to 200 °C, and the heating time is preferably 10 to 180 seconds. Also, the pressure during vacuum drying is preferably about 1 to 1.0×10 5 Pa. The obtained composition layer is usually exposed using an exposure machine. The exposure machine may be an immersion exposure machine. As the exposure light source, those that emit laser light in the ultraviolet region such as KrF excimer laser (wavelength 248 nm), ArF excimer laser (wavelength 193 nm), F2 excimer laser (wavelength 157 nm), those that convert laser light from a solid laser light source (YAG or semiconductor laser, etc.) into harmonic laser light in the far ultraviolet region or vacuum ultraviolet region and emit it, those that irradiate electron beams, extreme ultraviolet light (EUV), etc., various ones can be used. In this specification, irradiating these radiations may be collectively referred to as "exposure". During exposure, usually, exposure is performed through a mask corresponding to the required pattern. When the exposure light source is an electron beam, exposure may be performed by direct drawing without using a mask. The composition layer after exposure is heat-treated (so-called post-exposure bake) to promote the deprotection reaction in the acid-labile group. The heating temperature is usually about 50 to 200 °C, preferably about 70 to 150 °C. The composition layer after heating is usually developed using a developing solution with a developing device. Examples of the developing method include dip method, paddle method, spray method, dynamic dispense method, etc. The developing temperature is preferably, for example, 5 to 60 °C, and the developing time is preferably, for example, 5 to 300 seconds. By selecting the type of developing solution as follows, a positive resist pattern or a negative resist pattern can be manufactured. When producing a positive resist pattern from the resist composition of the present invention, an alkaline developer is used as the developer. The alkaline developer may be any of various alkaline aqueous solutions used in this field. For example, aqueous solutions of tetramethylammonium hydroxide, (2-hydroxyethyl)trimethylammonium hydroxide (commonly known as choline), etc. can be mentioned. The alkaline developer may contain a surfactant. After development, it is preferable to wash the resist pattern with ultrapure water and then remove the water remaining on the substrate and the pattern. When producing a negative resist pattern from the resist composition of the present invention, a developer containing an organic solvent (hereinafter sometimes referred to as an "organic-based developer") is used as the developer. Examples of the organic solvent contained in the organic-based developer include ketone solvents such as 2-hexanone and 2-heptanone; glycol ether ester solvents such as propylene glycol monomethyl ether acetate; ester solvents such as butyl acetate; glycol ether solvents such as propylene glycol monomethyl ether; amide solvents such as N,N-dimethylacetamide; aromatic hydrocarbon solvents such as anisole, etc. In the organic-based developer, the content of the organic solvent is preferably 90% by mass or more and 100% by mass or less, more preferably 95% by mass or more and 100% by mass or less, and even more preferably substantially only the organic solvent. Among them, as the organic-based developer, a developer containing butyl acetate and / or 2-heptanone is preferable. In the organic-based developer, the total content of butyl acetate and 2-heptanone is preferably 50% by mass or more and 100% by mass or less, more preferably 90% by mass or more and 100% by mass or less, and even more preferably substantially only butyl acetate and / or 2-heptanone. The organic-based developer may contain a surfactant. Also, the organic-based developer may contain a trace amount of water. During development, the development may be stopped by substituting with a solvent of a different type from the organic-based developer. It is preferable to wash the developed resist pattern with a rinsing solution. The rinsing solution is not particularly limited as long as it does not dissolve the resist pattern, and a solution containing a general organic solvent can be used, preferably an alcohol solvent or an ester solvent. After washing, it is preferable to remove the rinsing solution remaining on the substrate and the pattern.

[0246] <Use> The resist composition of the present invention is suitable as a resist composition for KrF excimer laser exposure, a resist composition for ArF excimer laser exposure, a resist composition for electron beam (EB) exposure, or a resist composition for EUV exposure, particularly suitable as a resist composition for electron beam (EB) exposure or a resist composition for EUV exposure, and is useful for semiconductor microfabrication.

Examples

[0247] The present invention will be described more specifically with reference to examples. In the examples, “%” and “parts” representing content or usage amount are based on mass unless otherwise specified. The weight average molecular weight is a value determined by gel permeation chromatography. The analysis conditions for gel permeation chromatography are as follows. Column: TSKgel Multipore HXL-M x 3 + guard column (manufactured by Tosoh Corporation) Eluent: Tetrahydrofuran Flow rate: 1.0 mL / min Detector: RI detector Column temperature: 40 °C Injection volume: 100 μl Molecular weight standard: Standard polystyrene (manufactured by Tosoh Corporation) The structure of the compound was confirmed by measuring the molecular ion peak using mass spectrometry (LC is Agilent model 1100, MASS is Agilent LC / MSD model). In the following examples, the value of this molecular ion peak is indicated by “MASS”.

[0248] Example 1: Synthesis of the salt represented by formula (I-654) In TIFF0007716229000148.tif, 20 parts of the compound represented by formula (I-654-a), 2.28 parts of the compound represented by formula (I-654-c), 100 parts of ethyl acetate, and 15 parts of tetrahydrofuran were mixed and stirred at 23°C for 30 minutes. To the resulting mixed solution, 6.55 parts of the compound represented by formula (I-654-b) were added, and the mixture was stirred at 23°C for 18 hours. To the resulting reaction mass, 20 parts of n-heptane and 70 parts of ion-exchanged water were added, and the mixture was stirred at 23°C for 30 minutes, followed by liquid separation to obtain the organic layer. To the recovered organic layer, 60 parts of ion-exchanged water were added, and the mixture was stirred at 23°C for 30 minutes, followed by liquid separation to obtain the organic layer. This water washing operation was repeated 4 times. The obtained organic layer was concentrated, and the concentrated mass was fractionated by column (silica gel 60N (spherical, neutral) 100-210 μm; manufactured by Kanto Chemical Co., Inc., developing solvent: n-heptane / ethyl acetate = 1 / 1) to obtain 7.48 parts of the compound represented by formula (I-654-d). In TIFF0007716229000149.tif, 0.95 part of the compound represented by formula (I-654-d) and 10 parts of tetrahydrofuran were mixed and stirred at 23°C for 30 minutes, then cooled to 5°C, and 0.14 part of sodium hydride was added. To the resulting mixture, 1.01 part of the salt represented by formula (I-654-e) was added, and the mixture was stirred at 5°C for 3 hours. To the resulting mixture, 6.30 parts of 1N hydrochloric acid were added, then the temperature was raised to 23°C, and the mixture was stirred at 23°C for 6 hours. To the resulting mixture, 30 parts of chloroform and 15 parts of ion-exchanged water were added, and the mixture was stirred at 23°C for 30 minutes, followed by liquid separation to obtain the organic layer. After concentrating the obtained organic layer, to the concentrated residue, 1 part of acetonitrile and 30 parts of tert-butyl methyl ether were added, and the mixture was stirred at 23°C for 30 minutes, then the supernatant was removed and concentrated to obtain 1.24 parts of the salt represented by formula (I-654-f). 0.62 part of the salt represented by formula (I-654-f) and 30 parts of dimethylformamide were mixed and stirred at 23 °C for 30 minutes. Then, 0.16 part of potassium carbonate and 0.05 part of potassium iodide were added, and the temperature was raised to 75 °C. To the resulting mixture, 0.45 part of the compound represented by formula (I-654-g) was added, and the mixture was stirred at 75 °C for 5 hours and then cooled to 23 °C. To the resulting mixture, 50 parts of chloroform and 20 parts of a 5% aqueous oxalic acid solution were added and stirred at 23 °C for 30 minutes, and then the layers were separated to obtain the organic layer. To the obtained organic layer, 20 parts of ion-exchanged water was added and stirred at 23 °C for 30 minutes, and then the layers were separated to obtain the organic layer. This water washing operation was repeated 5 times. By concentrating the obtained organic layer, 0.71 part of the salt represented by formula (I-654-h) was obtained. 0.68 part of the salt represented by formula (I-654-h), 0.51 part of the salt represented by formula (I-654-i), 30 parts of chloroform and 15 parts of ethyl acetate were mixed and stirred at 23 °C for 2 hours. To the resulting mixture, 20 parts of ion-exchanged water was added and stirred at 23 °C for 30 minutes, and then the layers were separated to obtain the organic layer. This water washing operation was repeated 5 times. The obtained organic layer was concentrated, 30 parts of tert-butyl methyl ether was added to the concentrated residue and stirred at 23 °C for 30 minutes, and then filtered to obtain 0.89 part of the salt represented by formula (I-654). MASS(ESI(+)Spectrum):M + 813.1 MASS(ESI(-)Spectrum):M - 517.1

[0249] Example 2: Synthesis of the salt represented by formula (I-662) 0.68 part of the salt represented by formula (I-654-h), 0.45 part of the salt represented by formula (I-662-i), 30 parts of chloroform and 15 parts of ethyl acetate were mixed and stirred at 23 °C for 2 hours. To the resulting mixture, 20 parts of ion-exchanged water was added and stirred at 23 °C for 30 minutes, then liquid separation was carried out to take out the organic layer. This water washing operation was repeated 5 times. The obtained organic layer was concentrated, 30 parts of tert-butyl methyl ether was added to the concentrated residue and stirred at 23 °C for 30 minutes, and then 0.79 part of the salt represented by formula (I-662) was obtained by filtration. MASS(ESI(+)Spectrum):M + 813.1 MASS(ESI(-)Spectrum):M - 467.1

[0250] Example 3: Synthesis of the salt represented by formula (I-274) 3.80 parts of the compound represented by formula (I-274-a) and 6.40 parts of Oxone® were mixed, stirred at 23 °C for 30 minutes, and then cooled to 5 °C. After adding 23.56 parts of sulfuric acid to the resulting mixture, it was stirred at 5 °C for 30 minutes. A mixed solution of 3.68 parts of the compound represented by formula (I-274-b) and 18.40 parts of chloroform was added to the resulting mixture, stirred at 5 °C for 30 minutes, and then further stirred at 23 °C for 2 hours. The obtained mixed solution was added to 120 parts of methanol and stirred at 23 °C for 30 minutes, and then filtered. After concentrating the obtained filtrate, 125 parts of chloroform and 25 parts of acetonitrile were added to the concentrated residue, stirred at 23 °C for 30 minutes, 60 parts of 5% hydrochloric acid was added and stirred at 23 °C for 30 minutes, and then liquid separation was carried out to take out the organic layer. 40 parts of ion-exchanged water was added to the obtained organic layer and stirred at 23 °C for 30 minutes, and then liquid separation was carried out to take out the organic layer. This water washing operation was repeated 3 times. The obtained organic layer was concentrated, 45 parts of tert-butyl methyl ether was added to the concentrated mixture, stirred at 23 °C for 30 minutes, and 2.37 parts of the salt represented by formula (I-274-c) was obtained by filtration. 0.95 part of the compound represented by TIFF0007716229000154.tif42138 (I-654-d) and 10 parts of tetrahydrofuran were mixed and stirred at 23 °C for 30 minutes, then cooled to 5 °C, and 0.14 part of sodium hydride was added. To the resulting mixture, 2.32 parts of the salt represented by formula (I-274-c) was added and stirred at 5 °C for 3 hours. To the resulting mixture, 6.30 parts of 1N hydrochloric acid was added, then the temperature was raised to 23 °C and stirred at 23 °C for 6 hours. To the resulting mixture, 30 parts of chloroform and 15 parts of ion-exchanged water were added, stirred at 23 °C for 30 minutes, then separated and the organic layer was taken out. After concentrating the obtained organic layer, 1 part of acetonitrile and 30 parts of tert-butyl methyl ether were added to the concentrated residue, stirred at 23 °C for 30 minutes, then the supernatant was removed and concentrated to obtain 2.19 parts of the salt represented by formula (I-274-f). 1.37 parts of the salt represented by TIFF0007716229000155.tif33155 (I-274-f) and 30 parts of dimethylformamide were mixed and stirred at 23 °C for 30 minutes, then 0.16 part of potassium carbonate and 0.05 part of potassium iodide were added and the temperature was raised to 75 °C. To the resulting mixture, 0.45 part of the compound represented by formula (I-654-g) was added and stirred at 75 °C for 5 hours, then cooled to 23 °C. To the resulting mixture, 50 parts of chloroform and 20 parts of 5% aqueous oxalic acid solution were added and stirred at 23 °C for 30 minutes, then separated and the organic layer was taken out. To the obtained organic layer, 20 parts of ion-exchanged water was added, stirred at 23 °C for 30 minutes, then separated and the organic layer was taken out. This water washing operation was repeated 5 times. By concentrating the obtained organic layer, 1.15 parts of the salt represented by formula (I-274-g) was obtained. 0.52 parts of the salt represented by TIFF0007716229000156.tif62155 (I-274-g), 0.51 parts of the salt represented by formula (I-654-i), 30 parts of chloroform and 15 parts of ethyl acetate were mixed and stirred at 23 °C for 2 hours. To the resulting mixture, 20 parts of ion-exchanged water was added and stirred at 23 °C for 30 minutes, then liquid-separated to take out the organic layer. This water-washing operation was repeated 5 times. The obtained organic layer was concentrated, 30 parts of tert-butyl methyl ether was added to the concentrated residue and stirred at 23 °C for 30 minutes, and then filtered to obtain 0.69 parts of the salt represented by formula (I-274). MASS(ESI(+)Spectrum):M + 617.1 MASS(ESI(-)Spectrum):M - 517.1

[0251] Example 4: Synthesis of the salt represented by formula (I-282) 0.52 parts of the salt represented by TIFF0007716229000157.tif64160 (I-274-g), 0.45 parts of the salt represented by formula (I-662-i), 30 parts of chloroform and 15 parts of ethyl acetate were mixed and stirred at 23 °C for 2 hours. To the resulting mixture, 20 parts of ion-exchanged water was added and stirred at 23 °C for 30 minutes, then liquid-separated to take out the organic layer. This water-washing operation was repeated 5 times. The obtained organic layer was concentrated, 30 parts of tert-butyl methyl ether was added to the concentrated residue and stirred at 23 °C for 30 minutes, and then filtered to obtain 0.70 parts of the salt represented by formula (I-282). MASS(ESI(+)Spectrum):M + 617.1 MASS(ESI(-)Spectrum):M - 467.1

[0252] Example 5: Synthesis of the salt represented by formula (I-268) 0.52 parts of the salt represented by TIFF0007716229000158.tif64157 (I-274-g), 0.35 parts of the salt represented by formula (I-268-i), 30 parts of chloroform and 15 parts of ethyl acetate were mixed and stirred at 23 °C for 2 hours. To the resulting mixture, 20 parts of ion-exchanged water was added and stirred at 23 °C for 30 minutes, and then liquid separation was carried out to take out the organic layer. This water washing operation was repeated 5 times. The obtained organic layer was concentrated, 30 parts of tert-butyl methyl ether was added to the concentrated residue and stirred at 23 °C for 30 minutes, and then filtered to obtain 0.67 parts of the salt represented by formula (I-268). MASS(ESI(+)Spectrum):M + 617.1 MASS(ESI(-)Spectrum):M - 339.1

[0253] Example 6: Synthesis of the salt represented by formula (I-1080) 6.57 parts of the compound represented by TIFF0007716229000159.tif37139 (I-1080-a), 0.23 parts of the compound represented by formula (I-654-c), 30 parts of ethyl acetate and 15 parts of tetrahydrofuran were mixed and stirred at 23 °C for 30 minutes. To the resulting mixed solution, 0.66 parts of the compound represented by formula (I-654-b) was added and stirred at 23 °C for 18 hours. To the obtained reaction mass, 100 parts of n-heptane and 20 parts of ion-exchanged water were added and stirred at 23 °C for 30 minutes, and then liquid separation was carried out to take out the organic layer. 20 parts of ion-exchanged water was added to the recovered organic layer and stirred at 23 °C for 30 minutes, and then liquid separation was carried out to take out the organic layer. This water washing operation was repeated 4 times. The obtained organic layer was concentrated, and the concentrated mass was fractionated by a column (silica gel 60N (spherical, neutral) 100 - 210 μm; manufactured by Kanto Chemical Co., Inc., developing solvent: n-heptane / ethyl acetate = 1 / 1) to obtain 6.28 parts of the compound represented by formula (I-1080-d). 2.26 parts of the compound represented by the formula (I-1080-d) and 10 parts of tetrahydrofuran were mixed, stirred at 23 °C for 30 minutes, then cooled to 5 °C, and 0.14 part of sodium hydride was added. To the resulting mixture, 2.32 parts of the salt represented by the formula (I-274-c) was added, and the mixture was stirred at 5 °C for 3 hours. To the resulting mixture, 6.30 parts of 1N hydrochloric acid was added, then the temperature was raised to 23 °C, and the mixture was stirred at 23 °C for 6 hours. To the resulting mixture, 30 parts of chloroform and 15 parts of ion-exchanged water were added, stirred at 23 °C for 30 minutes, then separated, and the organic layer was taken out. After concentrating the obtained organic layer, 1 part of acetonitrile and 30 parts of tert-butyl methyl ether were added to the concentrated residue, stirred at 23 °C for 30 minutes, then the supernatant was removed and concentrated to obtain 1.01 parts of the salt represented by the formula (I-1080-f). 1.00 part of the salt represented by the formula (I-1080-f) and 30 parts of dimethylformamide were mixed, stirred at 23 °C for 30 minutes, then 0.08 part of potassium carbonate and 0.03 part of potassium iodide were added, and the temperature was raised to 75 °C. To the resulting mixture, 0.44 part of the compound represented by the formula (I-654-g) was added, and the mixture was stirred at 75 °C for 5 hours, then cooled to 23 °C. To the resulting mixture, 50 parts of chloroform and 20 parts of 5% aqueous oxalic acid solution were added, stirred at 23 °C for 30 minutes, then separated, and the organic layer was taken out. To the obtained organic layer, 20 parts of ion-exchanged water was added, stirred at 23 °C for 30 minutes, then separated, and the organic layer was taken out. This washing operation with water was repeated 5 times. By concentrating the obtained organic layer, 1.08 parts of the salt represented by the formula (I-1080-b) was obtained. 0.72 part of the salt represented by formula (I-1080-b), 0.45 part of the salt represented by formula (I-662-i), 30 parts of chloroform and 15 parts of ethyl acetate were mixed and stirred at 23 °C for 2 hours. To the resulting mixture, 20 parts of ion-exchanged water was added and stirred at 23 °C for 30 minutes, and then liquid separation was carried out to take out the organic layer. This water washing operation was repeated 5 times. The obtained organic layer was concentrated, 30 parts of tert-butyl methyl ether was added to the concentrated residue and stirred at 23 °C for 30 minutes, then the supernatant was removed and concentrated to obtain 0.88 part of the salt represented by formula (I-1080). MASS(ESI(+)Spectrum):M + 868.9 MASS(ESI(-)Spectrum):M - 467.1

[0254] Example 7: Synthesis of the salt represented by formula (I-1460) 2.26 parts of the compound represented by formula (I-1080-d), 0.78 part of the salt represented by formula (I-654-e) and 30 parts of dimethylformamide were mixed and stirred at 23 °C for 30 minutes, and then the temperature was raised to 90 °C. To the resulting mixture, 1.44 parts of potassium carbonate was added and stirred at 90 °C for 3 hours. To the obtained mixture, 6.30 parts of 1N hydrochloric acid was added, then the temperature was raised to 23 °C and stirred at 23 °C for 6 hours. To the obtained mixture, 50 parts of chloroform and 30 parts of ion-exchanged water were added and stirred at 23 °C for 30 minutes, and then liquid separation was carried out to take out the organic layer. To the obtained organic layer, 30 parts of ion-exchanged water was added and stirred at 23 °C for 30 minutes, and then liquid separation was carried out to take out the organic layer. This water washing operation was repeated 3 times. After the obtained organic layer was concentrated, 3 parts of acetonitrile and 30 parts of tert-butyl methyl ether were added to the concentrated residue and stirred at 23 °C for 30 minutes, then the supernatant was removed and concentrated to obtain 1.63 parts of the salt represented by formula (I-1460-f). 1.21 parts of the salt represented by TIFF0007716229000164.tif52148 formula (I-1460-f) and 30 parts of dimethylformamide were mixed and stirred at 23 °C for 30 minutes. Then, 0.16 part of potassium carbonate and 0.05 part of potassium iodide were added, and the temperature was raised to 75 °C. To the obtained mixture, 0.90 part of the compound represented by formula (I-654-g) was added, and the mixture was stirred at 75 °C for 5 hours and then cooled to 23 °C. To the obtained mixture, 50 parts of chloroform and 20 parts of 5% aqueous oxalic acid solution were added and stirred at 23 °C for 30 minutes, and then the layers were separated to take out the organic layer. To the obtained organic layer, 20 parts of ion-exchanged water were added and stirred at 23 °C for 30 minutes, and then the layers were separated to take out the organic layer. This water washing operation was repeated 5 times. By concentrating the obtained organic layer, 1.39 parts of the salt represented by formula (I-1460-h) were obtained. 1.08 parts of the salt represented by TIFF0007716229000165.tif47153 formula (I-1460-h), 0.45 part of the salt represented by formula (I-662-i), 30 parts of chloroform and 15 parts of ethyl acetate were mixed and stirred at 23 °C for 2 hours. To the obtained mixture, 20 parts of ion-exchanged water were added and stirred at 23 °C for 30 minutes, and then the layers were separated to take out the organic layer. This water washing operation was repeated 5 times. The obtained organic layer was concentrated, 30 parts of tert-butyl methyl ether were added to the concentrated residue and stirred at 23 °C for 30 minutes, then the supernatant was removed and concentrated to obtain 1.38 parts of the salt represented by formula (I-1460). MASS(ESI(+)Spectrum):M + 1316.7 MASS(ESI(-)Spectrum):M - 467.1

[0255] Example 8: Synthesis of the salt represented by formula (I-1042) 0.58 part of the salt represented by formula (I-274-f) and 30 parts of chloroform were mixed and stirred at 23 °C for 30 minutes. To the resulting mixed solution, 0.19 part of the compound represented by formula (I-1042-a) was added, and the mixture was further stirred at 50 °C for 2 hours. To the resulting mixed solution, 0.13 part of the compound represented by formula (I-1042-b) was added, and the mixture was further stirred at 50 °C for 3 hours and then cooled to 23 °C. To the resulting mixture, 15 parts of a 5% aqueous oxalic acid solution was added and stirred at 23 °C for 30 minutes, and then the layers were separated to obtain the organic layer. To the obtained organic layer, 15 parts of ion-exchanged water was added and stirred at 23 °C for 30 minutes, and then the layers were separated to obtain the organic layer. This water washing operation was repeated 5 times. The obtained organic layer was concentrated, 30 parts of tert-butyl methyl ether was added to the concentrated residue, and the mixture was stirred at 23 °C for 30 minutes. Then, the supernatant was removed and concentrated to obtain 0.63 part of the salt represented by formula (I-1042-h). 0.51 part of the salt represented by formula (I-1042-h), 0.45 part of the salt represented by formula (I-662-i), 30 parts of chloroform and 15 parts of ethyl acetate were mixed and stirred at 23 °C for 2 hours. To the resulting mixture, 20 parts of ion-exchanged water was added and stirred at 23 °C for 30 minutes, and then the layers were separated to obtain the organic layer. This water washing operation was repeated 5 times. The obtained organic layer was concentrated, 30 parts of tert-butyl methyl ether was added to the concentrated residue, and the mixture was stirred at 23 °C for 30 minutes. Then, the supernatant was removed and concentrated to obtain 0.65 part of the salt represented by formula (I-1042). MASS(ESI(+)Spectrum):M + 603.1 MASS(ESI(-)Spectrum):M - 467.1

[0256] Synthesis of resin The compounds (monomers) used for the synthesis of resin (A) are shown below. Hereinafter, these compounds are referred to as "monomer (a1-1-3)" etc. according to their formula numbers. TIFF0007716229000168.tif43144

[0257] Synthesis Example 1: Synthesis of Resin A1 As monomers, monomer (a1-1-3), monomer (a1-2-6), monomer (a2-1-1) and monomer (a3-4-2) were used, and they were mixed so that the molar ratio [monomer (a1-1-3): monomer (a1-2-6): monomer (a2-1-1): monomer (a3-4-2)] was 45:14:2.5:38.5. Propylene glycol monomethyl ether acetate 1.5 times the mass of the total monomer amount was added to form a solution. To this solution, azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were added as initiators at 1 mol% and 3 mol%, respectively, based on the total monomer amount, and these were heated at 73 °C for about 5 hours. The obtained reaction mixture was poured into a large amount of methanol / water mixed solvent to precipitate the resin, and this resin was filtered. The obtained resin was dissolved again in propylene glycol monomethyl ether acetate, and the resulting solution was poured into a methanol / water mixed solvent to precipitate the resin, and this resin was filtered. The reprecipitation operation was performed twice, and resin A1 with a weight average molecular weight of 7.8×10 3 was obtained in a yield of 69%. This resin A1 has the following structural units. TIFF0007716229000169.tif36126

[0258] Synthesis Example 2: Synthesis of Resin X1 As monomers, monomer (a5-1-1) and monomer (a4-0-12) were used, and they were mixed so that the molar ratio [monomer (a5-1-1): monomer (a4-0-12)] was 50:50. Methyl isobutyl ketone 1.2 times the mass of the total monomer amount was added to form a solution. To this solution, azobis(2,4-dimethylvaleronitrile) was added as an initiator at 3 mol% based on the total monomer amount, and it was heated at 70 °C for about 5 hours. The obtained reaction mixture was poured into a large amount of methanol / water mixed solvent to precipitate the resin, and this resin was filtered, and resin X1 with a weight average molecular weight of 1.0×10 4 was obtained in a yield of 91%. This resin X1 has the following structural units. TIFF0007716229000170.tif3082

[0259] <Preparation of Resist Composition> As shown in Table 2, each of the following components was mixed, and the resulting mixture was filtered through a fluororesin filter with a pore size of 0.2 μm to prepare a resist composition.

Table 2

[0260] <Resin> A1, X1: Resin A1, Resin X1 <Salt (I)> I-268: Salt represented by formula (I-268) I-274: Salt represented by formula (I-274) I-282: Salt represented by formula (I-282) I-654: Salt represented by formula (I-654) I-662: Salt represented by formula (I-662) I-1042: Salt represented by formula (I-1042) I-1080: Salt represented by formula (I-1080) I-1192: Salt represented by formula (I-1192) <Acid Generator> IX-1 IX-2 IX-3 IX-4 IX-5 TIFF0007716229000172.tif82153<Compound (D)> D1: (manufactured by Tokyo Chemical Industry Co., Ltd.) TIFF0007716229000173.tif1932<Solvent> 400 parts of propylene glycol monomethyl ether acetate 100 parts of propylene glycol monomethyl ether 5 parts of γ-butyrolactone

[0261] <Manufacture and Evaluation of Resist Pattern> An organic antireflective film composition (ARC-29; manufactured by Nissan Chemical Industries, Ltd.) was applied to a silicon wafer and baked at 205°C for 60 seconds to form an organic antireflective film with a film thickness of 78 nm on the wafer. Next, the above resist composition was applied (spin-coated) onto this organic antireflective film so that the film thickness after drying would be 85 nm. After application, the silicon wafer was prebaked on a direct hot plate at the temperature described in the "PB" column of Table 2 for 60 seconds to form a composition layer. The silicon wafer on which the composition layer was formed was exposed using an ArF excimer stepper for immersion lithography (XT: 1900Gi; manufactured by ASML, NA = 1.35, 3 / 4 Annular X-Y polarization) with a mask for forming a contact hole pattern (hole pitch 90 nm / hole diameter 55 nm), and the exposure dose was changed stepwise for exposure. Note that ultrapure water was used as the immersion medium. After exposure, post-exposure baking was performed on a hot plate at the temperature described in the "PEB" column of Table 2 for 60 seconds. Next, the composition layer on this silicon wafer was developed using butyl acetate (manufactured by Tokyo Chemical Industry Co., Ltd.) as a developer at 23°C for 20 seconds by the dynamic dispense method to produce a negative resist pattern.

[0262] In the resist pattern obtained after development, the exposure dose at which the hole diameter formed using the mask became 50 nm was defined as the effective sensitivity.

[0263] <CD Uniformity (CDU) Evaluation> At the effective sensitivity, the hole diameter of the pattern formed with a mask having a hole diameter of 55 nm was measured 24 times for each hole, and the average value was taken as the average hole diameter of one hole. The standard deviation was determined using as the population the measurement of the average hole diameter of the patterns formed with a mask having a hole diameter of 55 nm at 400 locations within the same wafer. The results are shown in Table 3. The numerical values in the table indicate the standard deviation (nm).

Table 3

Industrial Applicability

[0264] The salt of the present invention and the resist composition containing the salt are suitable for fine processing of semiconductors and industrially useful because a resist pattern having good CD uniformity can be obtained.

Claims

1. A salt represented by formula (I). [In formula (I), R １ and R ２ each independently represents —O—R １０ —O—CO—R １０ —O—CO—O—R １０ —O—L １０ —CO—O—R １０ respectively. L １０ represents an alkanediyl group having 1 to 6 carbon atoms. R ４ 、 R ５ 、 R ７ and R ８ each independently represents a halogen atom, a C1-C4 fluoroalkyl group, a C1-C6 alkyl group, a hydroxy group or a C1-C6 alkoxy group. R １０ represents a group having a cyclic carbonate structure represented by formula (x1) to formula (x15). X １ and X ２ each independently represents an oxygen atom or a sulfur atom. m1 represents an integer of any one of 1 to 5, and when m1 is 2 or more, the groups in a plurality of parentheses may be the same as or different from each other. m2 represents an integer of any one of 0 to 5, and when m2 is 2 or more, the groups in a plurality of parentheses may be the same as or different from each other. m4 represents any integer from 0 to 4, and when m4 is 2 or more, the plurality of Rs ４ may be the same as or different from each other. m5 represents any integer from 0 to 4, and when m5 is 2 or more, the plurality of Rs ５ may be the same as or different from each other. m7 represents any integer from 0 to 4, and when m7 is 2 or more, a plurality of Rs ７ may be the same as or different from each other. m8 represents any integer from 0 to 5, and when m8 is 2 or more, the plurality of Rs ８ may be the same as or different from each other. However, 1 ≦ m1 + m7 ≦ 5, 0 ≦ m2 + m8 ≦ 5. AI － represents an anion represented by the formula (I-A). [In formula (I-A), Q １ and Q ２ each independently represents a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms. L １ represents a group represented by any one of formulas (b1-1) to (b1-3). Y １ represents an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and the -CH ２ - in the alicyclic hydrocarbon group may be replaced by -O-, -SO ２ - or -CO-.] [In formula (b1-1), L ｂ２ represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms. L ｂ３ represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group, and -CH ２ - contained in the saturated hydrocarbon group may be replaced with -O- or -CO-. However, L ｂ２ and L ｂ３ The total number of carbon atoms of and is 22 or less. In formula (b1-2), L ｂ４ represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms. L ｂ５ represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms or hydroxy groups, and -CH ２ - contained in the saturated hydrocarbon group may be replaced with -O- or -CO-. However, the total number of carbon atoms of L ｂ４ and L ｂ５ is 22 or less. In formula (b1-3), L ｂ６ represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms or hydroxy groups. L ｂ７ represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, and the hydrogen atoms contained in the saturated hydrocarbon group may be substituted with fluorine atoms or hydroxy groups, and -CH ２ - contained in the saturated hydrocarbon group may be replaced by -O- or -CO-. However, L ｂ６ and L ｂ７ The total number of carbon atoms of and is 23 or less. In formula (b1-1), formula (b1-2) and formula (b1-3), * and ** each represent a bonding site, and * represents a bonding site with -Y1.]

2. X １ and X ２ The salt according to claim 1, wherein and are oxygen atoms.

3. R １０ The salt according to claim 1 or 2, wherein the group having a cyclic carbonate structure of

4. m2 is 0, m8 is 1, and R ８ is a branched alkyl group having 3 or 4 carbon atoms, the salt according to any one of claims 1 to 3.

5. R ４ or R ５ is an iodine atom, a fluorine atom or a trifluoromethyl group, the salt according to any one of claims 1 to 4.

6. R in the benzene ring ４ is bonded to X １ at the ortho or meta position, or R ５ in the benzene ring is bonded to X ２ at the ortho or meta position relative to X, the salt according to claim 5.

7. An acid generator containing the salt according to any one of Claims 1 to 6.

8. A resist composition containing the acid generator according to Claim 7 and a resin having an acid-labile group.

9. The resist composition according to Claim 8, wherein the resin having an acid-labile group contains at least one selected from the group consisting of a structural unit represented by formula (a1-1) and a structural unit represented by formula (a1-2). [In formula (a1-1) and formula (a1-2), L ａ１ and L ａ２ each independently represents -O- or *-O-(CH ２ ) ｋ１ -CO-O-, k1 represents any integer from 1 to 7, and * represents a bond with -CO-. 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 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. m1 represents an integer of any one of 0 to 14. n1 represents an integer of any one of 0 to 10. n1' represents an integer of any one of 0 to 3.]

10. The resist composition according to Claim 8 or 9, further containing a resin containing a structural unit having a fluorine atom.

11. The resist composition according to any one of Claims 8 to 10, further containing a salt that generates an acid having a lower acidity than the acid generated from the acid generator.

12. (1) A step of applying the resist composition according to any one of Claims 8 to 11 on a substrate, [[ID= ​ ​ ​ ​

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