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

Abstract

To provide a salt, an acid generator and a resist composition capable of producing a resist pattern having good line edge roughness (LER).SOLUTION: There are provided a salt represented by a specific structure, an acid generator, and a resist composition containing the same.SELECTED DRAWING: None

Description

[Technical Field]

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

[0002] Patent Document 1 describes a salt represented by the following formula and a resist composition containing the salt as an acid generator: Things are listed. JPEG2026027464000001.jpg2687 Patent Document 2 describes a salt represented by the following formula and a resist composition containing the salt as an acid generator: Things are listed. JPEG2026027464000002.jpg2687 Patent Document 3 discloses a salt represented by the following formula and a resist composition containing the salt as an acid generator: Each item is listed. JPEG2026027464000003.jpg6494 [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Publication No. 2020-015713 [Patent Document 2] Japanese Patent Publication No. 2020-015716 [Patent Document 3] Japanese Patent Application Publication No. 2020-046661 Summary of the Invention [Problem to be solved by the invention]

[0004] The present invention provides a resist pattern formed from a resist composition containing the above salt. and to provide a salt that forms a resist pattern with good line edge roughness (LER). The following are the challenges. [Means for solving the problem]

[0005] The present invention includes the following inventions. [1] An acid generator containing a salt represented by formula (I). JPEG2026027464000004.jpg10094 [In formula (I), R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each independently a halogen atom, a group having 1 carbon atom, a haloalkyl group having 1 to 12 carbon atoms or a hydrocarbon group having 1 to 18 carbon atoms, and the hydrocarbon group is The haloalkyl group and the —CH2— contained in the hydrocarbon group may have an —O— , -S-, -SO2- or -CO-. A 1 , A 2 and A 3 each independently represents a hydrocarbon group having 2 to 20 carbon atoms, One of the -CH2- contained in the hydrogen group is -O-, -CO-, -S- or -SO2-. It may be replaced. m1 represents an integer of 1 to 5, and when m1 is 2 or more, the groups in the parentheses are mutually exclusive. They may be the same or different. m2 represents an integer of 0 to 5, and when m2 is 2 or more, the groups in the parentheses are mutually exclusive. They may be the same or different. m3 represents an integer of 0 to 5, and when m3 is 2 or more, the groups in the parentheses are mutually exclusive. They may be the same or different. m4 represents an integer of 0 to 5, and when m4 is 2 or more, a plurality of R 4 are the same as each other They may be the same or different. m5 represents an integer of 0 to 5, and when m5 is 2 or more, a plurality of R 5 are the same as each other They may be the same or different. m6 represents an integer of 0 to 5, and when m6 is 2 or more, a plurality of R 6 are the same as each other They may be the same or different. m7 represents an integer of 0 to 4, and when m7 is 2 or more, a plurality of R 7 are the same as each other They may be the same or different. m8 represents an integer of 0 to 5, and when m8 is 2 or more, a plurality of R 8 are the same as each other They may be the same or different. m9 represents an integer of 0 to 5, and when m9 is 2 or more, a plurality of R 9 are the same as each other They may be the same or different. However, 1≦m1+m7≦5, 0≦m2+m8≦5, and 0≦m3+m9≦5. AI - represents an organic anion. [2]A 1 But *-X 01 -L 01 -or*-L 01 -X 01 - and A 2 but,*- X 02 -L 02 -or*-L 02 -X 02 - and A 3 But *-X 03 -L 03 -or *-L 03 -X 03 -is (X 01 , X 02 and X 03 are each independently -O-, -CO-, -S- or -SO2-. 01 , L 02 and L 03 are each independently represents a hydrocarbon group having 1 to 19 carbon atoms. * represents R 4 , R 5 or R 6Benzene to which represents the bonding site to the ring. [3]X 01 , X 02 and X 03 are each independently -O- or -S-. [2] The acid generator according to claim 1. [4]L 01 , L 02 and L 03 are each independently an alkanediyl having 1 to 6 carbon atoms. The acid generator according to [2] or [3], wherein the acid generator is a group. [5]R 4 , R 5 and R 6 each independently represents a fluorine atom, an iodine atom, a group having 1 to 10 carbon atoms, 4 perfluoroalkyl group or an alkyl group having 1 to 4 carbon atoms (the alkyl group CH2- may be replaced by -O- or -CO-. The acid generator according to any one of the above. [6]R 7 , R 8 and R 9 each independently represents a fluorine atom, an iodine atom, a group having 1 to 10 carbon atoms, 4 perfluoroalkyl group or an alkyl group having 1 to 4 carbon atoms (the alkyl group CH2- may be replaced by -O- or -CO-. The acid generator according to any one of the above. [7] AI - However, sulfonate anion, sulfonylimide anion, sulfonylmethide The acid generator according to any one of [1] to [6], which is an anion or a carboxylate anion. [8] AI - is a sulfonate anion, and the sulfonate anion is represented by formula (IA). The acid generator according to any one of [1] to [7], wherein the anion is an anion selected from the group consisting of methyl, ... TIFF2026027464000005.tif2965[In formula (IA), Q1 and Q 2 are each independently a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 6 carbon atoms. Or it represents a perfluoroalkyl group having 1 to 6 carbon atoms. L 1 represents a saturated hydrocarbon group having 1 to 24 carbon atoms, and —CH 2- may be replaced by -O- or -CO-, and the water contained in the saturated hydrocarbon group The hydrogen atom may be substituted with a fluorine atom or a hydroxy group. Y 1 is a methyl group which may have a substituent or a methyl group having 3 to 4 carbon atoms which may have a substituent. 24 alicyclic hydrocarbon group, and -CH2- contained in the alicyclic hydrocarbon group is -O-, may be replaced by -S-, -SO2- or -CO-.] [9] A composition containing the acid generator according to any one of [1] to [8] and a resin having an acid labile group. A resist composition.

[10] The resin having an acid labile group is a structural unit represented by formula (a1-0), 1) and a structural unit represented by formula (a1-2) The resist composition according to [9], comprising at least one of the above. JPEG2026027464000006.jpg44148 [In formula (a1-0), formula (a1-1) and formula (a1-2), L a01 , L a1 and L a2 are each independently -O- or -O-(CH2) k1 - represents CO-O-, k1 represents an integer of 1 to 7, and * represents the bonding site with -CO-. represent. R a01 , R a4 and R a5 are each independently a hydrogen atom, a halogen atom or a halogen atom It represents an alkyl group having 1 to 6 carbon atoms which may have one or more atoms. R a02 , R a03 and R a04 are each independently an alkyl group having 1 to 8 carbon atoms, 18 alicyclic hydrocarbon groups, aromatic hydrocarbon groups having 6 to 18 carbon atoms, or combinations thereof Represents a group. R a6 and R a7 are each independently an alkyl group having 1 to 8 carbon atoms, an alkyl group having 2 to 8 carbon atoms, alkenyl group, alicyclic hydrocarbon group having 3 to 18 carbon atoms, aromatic hydrocarbon group having 6 to 18 carbon atoms or represents a group formed by combining these. m1 represents an integer of 0 to 14. n1 represents an integer of 0 to 10. n1' represents an integer of 0 to 3.

[11] The resin having an acid labile group contains a structural unit represented by formula (a2-A) [9] Or the resist composition according to

[10] . JPEG2026027464000007.jpg4654[In formula (a2-A), R a50 is a hydrogen atom, a halogen atom, or a group having 1 to 6 carbon atoms which may have a halogen atom represents an alkyl group represented by the formula: R a51 is a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, a Alkoxy group, alkoxyalkyl group having 2 to 12 carbon atoms, alkoxy group having 2 to 12 carbon atoms Alkoxy group, alkylcarbonyl group having 2 to 4 carbon atoms, alkylcarbonyl group having 2 to 4 carbon atoms It represents an oxy group, an acryloyloxy group, or a methacryloyloxy group. A a50 is a single bond or * -X a51 -(A a52 -X a52 ) nb - represents -R a50 is combined represents the bonding site with the carbon atom. 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 an integer of 0 to 4. When mb is an integer of 2 or more, multiple R in Numbers a51 may be the same or different from each other.

[12] The composition further contains a salt that generates an acid that is weaker in acidity than the acid generated from the acid generator. The resist composition according to any one of [9] to

[11] .

[13] (1) A method for coating a resist composition according to any one of [9] to

[12] on a substrate. a process of (2) drying the applied composition to form a composition layer; (3) exposing the composition layer to light; (4) heating the composition layer after exposure; and (5) A method for producing a resist pattern, comprising the step of developing the composition layer after heating.

[14] A salt represented by formula (I). JPEG2026027464000008.jpg10094 [In formula (I), R 4 , R 5 , R 6 , R 7 , R 8 and R 9 are each independently a halogen atom, a group having 1 carbon atom, a haloalkyl group having 1 to 12 carbon atoms or a hydrocarbon group having 1 to 18 carbon atoms, and the hydrocarbon group is The haloalkyl group and the —CH2— contained in the hydrocarbon group may have an —O— , -S-, -SO2- or -CO-. A 1 , A 2 and A 3each independently represents a hydrocarbon group having 2 to 20 carbon atoms, One of the -CH2- contained in the hydrogen group is -O-, -CO-, -S- or -SO2-. It may be replaced. m1 represents an integer of 1 to 5, and when m1 is 2 or more, the groups in the parentheses are mutually exclusive. They may be the same or different. m2 represents an integer of 0 to 5, and when m2 is 2 or more, the groups in the parentheses are mutually exclusive. They may be the same or different. m3 represents an integer of 0 to 5, and when m3 is 2 or more, the groups in the parentheses are mutually exclusive. They may be the same or different. m4 represents an integer of 0 to 5, and when m4 is 2 or more, a plurality of R 4 are the same as each other They may be the same or different. m5 represents an integer of 0 to 5, and when m5 is 2 or more, a plurality of R 5 are the same as each other They may be the same or different. m6 represents an integer of 0 to 5, and when m6 is 2 or more, a plurality of R 6 are the same as each other They may be the same or different. m7 represents an integer of 0 to 4, and when m7 is 2 or more, a plurality of R 7 are the same as each other They may be the same or different. m8 represents an integer of 0 to 5, and when m8 is 2 or more, a plurality of R 8 are the same as each other They may be the same or different. m9 represents an integer of 0 to 5, and when m9 is 2 or more, a plurality of R 9 are the same as each other They may be the same or different. However, 1≦m1+m7≦5, 0≦m2+m8≦5, and 0≦m3+m9≦5. AI - represents an organic anion.

[15] A 1 But *-X 01 -L 01 -or*-L 01 -X 01 - and A 2 but,* -X 02 -L 02 -or*-L 02 -X 02 - and A 3 But *-X 03 -L 03 -also *-L 03 -X 03 -is (X 01 , X 02 and X 03 are each independently -O- , -CO-, -S- or -SO2-. 01 , L 02 and L 03 are independent of each other represents a hydrocarbon group having 1 to 19 carbon atoms. * represents R 4 , R 5 or R 6 Benzene to which The salt according to

[14] , wherein the bonding site to the benzophenone ring is represented by the formula (14).

[16] X 01 , X 02 and X 03 are each independently -O- or -S-.

[17] L 01 , L 02 and L 03 are independently alkanediyl groups having 1 to 6 carbon atoms. The salt according to

[15] or

[16] , wherein the aryl group is a aryl group.

[18] R 4 , R 5 and R 6 are independently a fluorine atom, an iodine atom, and a carbon number of 1 perfluoroalkyl group having 1 to 4 carbon atoms or alkyl group having 1 to 4 carbon atoms (the alkyl group The salt according to any one of

[14] to

[0017] , wherein —CH2— may be replaced by —O— or —CO—.

[19] R7 , R 8 and R 9 are independently a fluorine atom, an iodine atom, and a carbon number of 1 perfluoroalkyl group having 1 to 4 carbon atoms or alkyl group having 1 to 4 carbon atoms (the alkyl group The salt according to any one of

[14] to

[0018] , wherein —CH2— may be replaced by —O— or —CO—.

[20] AI - However, sulfonate anion, sulfonylimide anion, sulfonylmethyl The salt according to any one of

[14] to

[19] , which is a carboxylic acid anion or a carboxylic acid anion.

[21] AI - is a sulfonate anion, and the sulfonate anion is represented by formula (IA): The salt according to any one of

[14] to

[20] , wherein the anion is TIFF2026027464000009.tif2965[In formula (IA), Q 1 and Q 2 are each independently a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 6 carbon atoms. Or it represents a perfluoroalkyl group having 1 to 6 carbon atoms. L 1 represents a saturated hydrocarbon group having 1 to 24 carbon atoms, and —CH 2- may be replaced by -O- or -CO-, and the water contained in the saturated hydrocarbon group The hydrogen atom may be substituted with a fluorine atom or a hydroxy group. Y 1 is a methyl group which may have a substituent or a methyl group having 3 to 4 carbon atoms which may have a substituent. 24 alicyclic hydrocarbon group, and -CH2- contained in the alicyclic hydrocarbon group is -O-, may be replaced by -S-, -SO2- or -CO-.] [Effects of the Invention]

[0006] By using a resist composition containing the salt of the present invention, good line edge roughness can be obtained. Resist patterns can be produced using laser elimination (LER). DETAILED DESCRIPTION OF THE INVENTION

[0007] In this specification, the term "(meth)acrylic monomer" refers to "acrylic monomer and "(Meth)acrylate" and "at least one methacrylic monomer" are used. The expressions "(meth)acrylic acid" and the like have the same meaning. In the case where the hydrocarbon group can have either a linear structure or a branched structure, either structure may be used. When -CH2- in the above is replaced with -O-, -S-, -CO- or -SO2-, The same examples apply to each group. A "combined group" refers to a group in which two exemplified groups are combined. It means a group obtained by appropriately modifying the valence, bonding form, etc. of the group. "Derived from" or "derived from" means that the polymerizable C=C bond contained in the molecule is converted into a single bond by polymerization. When stereoisomers exist, all stereoisomers are Includes: In this specification, the term "solid content of the resist composition" refers to the amount of the solid content of the resist composition that is the remaining amount of the resist composition. This refers to the total of all components excluding the solvent (E) described below.

[0008] [Salt represented by formula (I)] The present invention relates to a salt represented by formula (I) (hereinafter sometimes referred to as "salt (I)"). In salt (I), the side with a negative charge is called an anion (I), and the side with a positive charge is called a cationic It is sometimes called "On(I)". JPEG2026027464000010.jpg9994 [wherein all symbols have the same meanings as defined above.]

[0009] [Cation (I)] The cation (I) of the salt represented by formula (I) is a cation represented by formula (IC). JPEG2026027464000011.jpg100100 [In formula (IC), all symbols have the same meaning as in formula (I)]

[0010] R 4 , R 5 , R 6 , R 7 , R 8 and R 9 The halogen atoms include fluorine atoms and chlorine atoms. Examples of the fluorine atom include an iodine atom, a bromine atom, and an iodine atom. R 4 , R 5 , R 6 , R 7 , R 8 and R 9 The haloalkyl group having 1 to 12 carbon atoms is a haloalkyl group having 1 to 12 carbon atoms. represents an alkyl group having 1 to 12 carbon atoms and a fluorinated alkyl group having 1 to 12 carbon atoms; alkyl chloride having 1 to 12 carbon atoms, alkyl bromide having 1 to 12 carbon atoms, alkyl nitrile having 1 to 1 Examples of the haloalkyl group include alkyl iodides having 1 to 12 carbon atoms. Fluoroalkyl groups (trifluoromethyl, pentafluoroethyl, heptafluoro) propyl group, nonafluorobutyl group, etc.), 2,2,2-trifluoroethyl group, 3,3, 3-trifluoropropyl group, 4,4,4-trifluorobutyl group, and 3,3,4,4 , 4-pentafluorobutyl group, chloromethyl group, bromomethyl group, iodomethyl group, etc. The haloalkyl group preferably has 1 to 9 carbon atoms, more preferably 1 to 9 carbon atoms. It is preferably 6, more preferably 1 to 4, and even more preferably 1 to 3. R 4 , R 5 , R 6 , R 7, R 8 and R 9 Examples of the hydrocarbon group having 1 to 18 carbon atoms include arsenic, Acyclic hydrocarbon groups such as alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and combinations thereof Examples of the group include a group formed by reacting a The alkyl group includes methyl, ethyl, n-propyl, isopropyl, and n-butyl groups. 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 and dodecyl group groups, etc. The number of carbon atoms in the chain hydrocarbon group is preferably 1 to 12, more preferably 1 to 9. More preferably, it is 1 to 6, even more preferably, it is 1 to 4, and even more preferably, it is Usually it is 1 to 3.

[0011] The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and may be any of the groups shown below. The binding site can be at any position. JPEG2026027464000012.jpg46168Specifically, the monocyclic alicyclic hydrocarbon group includes a cyclopropyl group and a cyclobutyl group. , cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclo Examples of the polycyclic alicyclic hydrocarbon group include monocyclic cycloalkyl groups such as a decyl group. , a polycyclic cycloalkyl group such as a decahydronaphthyl group, an adamantyl group, or a norbornyl group The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 18, and more preferably is 3 to 16, and more preferably 3 to 12. Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenyl group, an anthryl group, The number of carbon atoms of the aromatic hydrocarbon group is preferably It is preferably 6 to 18, more preferably 6 to 14, and even more preferably 6 to 10. .

[0012] The group formed by combining an aromatic hydrocarbon group and a chain hydrocarbon group is A group combining an aromatic hydrocarbon group and an alkanediyl group, an alkyl group and an aromatic hydrocarbon group aromatic hydrocarbon group-*), a group that combines an alicyclic hydrocarbon group and a chain hydrocarbon group (e.g. , alicyclic hydrocarbon group-alkanediyl group-*, alkyl group-alicyclic hydrocarbon group-*), aromatic A group that combines an aromatic hydrocarbon group and an alicyclic hydrocarbon group (e.g., an aromatic hydrocarbon group-alicyclic hydrocarbon group) Examples include cyclic hydrocarbon groups-*, alicyclic hydrocarbon groups-aromatic hydrocarbon groups-*). * indicates a bond. Represents the binding site. Aromatic hydrocarbon groups -alkanediyl groups-* include alkanediyl groups such as benzyl and phenethyl groups. Examples include ralkyl groups. Examples of alkyl groups - aromatic hydrocarbon groups - include tolyl, xylyl, and cumenyl groups. Examples include: Alicyclic hydrocarbon groups - alkanediyl groups - * include cyclohexylmethyl groups, cyclohexylmethyl groups, Hexylethyl group, 1-(adamantan-1-yl)methyl group, 1-(adamantan-1 and cycloalkylalkyl groups such as (-1-methyl-yl)-1-methylethyl groups. Examples of alkyl groups - alicyclic hydrocarbon groups - include methylcyclohexyl, dimethylcyclohexyl, a cycloalkyl group having an alkyl group such as a 2-hexyl group or a 2-alkyladamantan-2-yl group Examples thereof include alkyl groups. Examples of aromatic hydrocarbon groups - alicyclic hydrocarbon groups - include phenylcyclohexyl groups. It can be obtained. Examples of alicyclic hydrocarbon groups - aromatic hydrocarbon groups - include cyclohexylphenyl groups. It can be obtained. In addition, in the combination, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and chain hydrocarbon groups In addition, when any of the groups is bonded to the benzene ring, two or more of the groups may be combined. That's fine.

[0013] The -CH2- contained in the haloalkyl group and the hydrocarbon group may be replaced with -O-, -S-, or -SO2- Or, the group substituted for -CO- is a hydroxy group (-CH2 contained in a methyl group) - is replaced by -O-), thiol group (-CH2- in the methyl group is replaced by -S -), carboxy group (-CH2-CH2- in the ethyl group is replaced by -O -CO- substituted), alkoxy group (-C at any position in the alkyl group H2- is replaced by -O-), alkoxycarbonyl group (a group contained in an alkyl group any one of -CH2-CH2- at any position is replaced by -O-CO-), alkylcarbonyl Nyl group (a group in which -CH2- at any position in an alkyl group is replaced with -CO-) ), alkylcarbonyloxy group (-CH2-CH2 at any position in the alkyl group) - is replaced by -CO-O-), alkylthio group (any group contained in an alkyl group) -CH2- at position 1 is replaced with -S-), alkylsulfonyl group (alkyl any -CH2- in any position is replaced by -SO2-), oxy group (methyl A group in which -CH2- in a ethylene group is replaced with -O-), a carbonyl group (a methyl group a thio group (a group in which -CH2- in a methylene group is replaced with -CO-), -CH2- in a methylene group is replaced with -S-), sulfonyl group (a group in which -CH2- in a methylene group is replaced with -S-) alkanediyloxy group (alkanediyloxy group in which -CH2- is replaced by -SO2-) A group in which any -CH2- in a diyl group is replaced with -O-), an alkane Diyloxycarbonyl group (-CH2-CH2 at any position in the alkanediyl group) - is replaced by -O-CO-), alkanediylcarbonyl group (alkanediyl a group in which any -CH2- at any position in the group is replaced with -CO-), an alkanediyl A carbonyloxy group (-CH2-CH2- at any position contained in an alkanediyl group) , -CO-O- substituted), alkanediylthio group (a group contained in an alkanediyl group) a group in which -CH2- at any position in the alkyl group is replaced with -S-), alkanediylsulfonyl A group (in which -CH2- at any position contained in an alkanediyl group is replaced with -SO2-) a cycloalkoxy group, a cycloalkylalkoxy group, an alkoxycarbonyloxy group, Aromatic hydrocarbon group-carbonyloxy group, aromatic hydrocarbon group-carbonyl group, aromatic Aromatic hydrocarbon group - oxy group, haloalkoxy group (haloalkyl group at any position) -CH2- is replaced with -O-), haloalkoxycarbonyl group (haloalkyl a group in which any -CH2-CH2- at any position in the group is replaced by -O-CO-), haloalkylcarbonyl group (wherein any -CH2- in the haloalkyl group is -C O-substituted), haloalkylcarbonyloxy group (a group contained in a haloalkyl group) (a group in which any -CH2-CH2- at any position is replaced by -CO-O-), Among these, groups in which two or more types are combined are exemplified. The alkoxy group includes an alkoxy group having 1 to 17 carbon atoms, such as methoxy. group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, oxy group octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, un The alkoxy group preferably has 1 to 11 carbon atoms, and More preferably, it is 1 to 6, even more preferably, it is 1 to 4, and even more preferably, it is 1 ~3. The alkoxycarbonyl group, alkylcarbonyl group and alkylcarbonyloxy group are A carbonyl group or a carbonyloxy group is bonded to the alkyl group or the alkoxy group. Represents a group. Examples of the alkoxycarbonyl group include alkoxycarbonyl groups having 2 to 17 carbon atoms. Examples of such groups include methoxycarbonyl, ethoxycarbonyl, and butoxycarbonyl groups. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 18 carbon atoms. Examples include an acetyl group, a propionyl group, and a butyryl group. Examples of the alkylcarbonyloxy group include alkylcarbonyloxy groups having 2 to 17 carbon atoms. Examples thereof include an acetyloxy group, a propionyloxy group, and a butyryloxy group. The number of carbon atoms in the alkoxycarbonyl group is preferably 2 to 11, and more preferably 2. The number of carbon atoms is preferably 1 to 6, more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkylcarbonyl group is preferably 2 to 12, and more preferably 2 to 6. It is more preferably 2 to 4, and even more preferably 2 or 3. The carbonyloxy group preferably has 2 to 11 carbon atoms, more preferably 2 to 6 carbon atoms. , more preferably 2 to 4, and even more preferably 2 or 3. The alkylthio group includes alkylthio groups having 1 to 17 carbon atoms, such as methyl. thio group, ethylthio group, propylthio group, butylthio group, pentylthio group, hexylthio group thio group, octylthio group, 2-ethylhexylthio group, nonylthio group, decylthio group, un The alkylthio group preferably has 1 to 11 carbon atoms, and More preferably, it is 1 to 6, even more preferably, it is 1 to 4, and even more preferably, it is 1 ~3. Examples of the alkylsulfonyl group include alkylsulfonyl groups having 1 to 17 carbon atoms. For example, a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, phenyl group, pentylsulfonyl group, hexylsulfonyl group, octylsulfonyl group, 2- Ethylhexylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, undecylsulfonyl group The alkylsulfonyl group preferably has 1 to 11 carbon atoms. More preferably, it is 1 to 6, even more preferably 1 to 4, and even more preferably is 1 to 3. Examples of the alkanediyloxy group include alkanediyloxy groups having 1 to 17 carbon atoms. Examples of such groups include methyleneoxy groups, ethyleneoxy groups, propanediyloxy groups, butanediyloxy groups, and the like. Examples of the carbon atom of the alkanediyloxy group include an alkanediyloxy group and a pentanediyloxy group. The number is preferably 1 to 11, more preferably 1 to 6, and even more preferably 1 to 11. It is 4, and even more preferably 1 to 3. The alkanediyloxycarbonyl group is an alkanediyloxy group having 2 to 17 carbon atoms. carbonyl groups, such as methyleneoxycarbonyl and ethyleneoxycarbonyl groups. Examples of the hydroxyl group include a propanediyloxycarbonyl group, a butanediyloxycarbonyl group, and the like. The alkanediylcarbonyl group is an alkanediylcarbonyl group having 2 to 18 carbon atoms. Examples of the alkyl group include a methylenecarbonyl group, an ethylenecarbonyl group, and a propanediyl group. Examples of the arylcarbonyl group include a butanediylcarbonyl group and a pentanediylcarbonyl group. The alkanediylcarbonyloxy group is an alkanediylcarbonyloxy group having 2 to 17 carbon atoms. Examples of such groups include a methylenecarbonyloxy group and an ethylenecarbonyloxy group. hydroxyl group, propanediylcarbonyloxy group, butanediylcarbonyloxy group, etc. The number of carbon atoms in the alkanediyloxycarbonyl group is preferably 2 to 11. , more preferably 2 to 6, even more preferably 2 to 4, and even more preferably The number of carbon atoms in the alkanediylcarbonyl group is preferably 2 to 12. More preferably, it is 2 to 6, even more preferably, it is 2 to 4, and even more preferably, it is 2 or 3. The number of carbon atoms in the alkanediylcarbonyloxy group is preferably 2 to 11. More preferably, it is 2 to 6, even more preferably 2 to 4, and even more preferably is 2 or 3. Examples of the alkanediylthio group include alkanediylthio groups having 1 to 17 carbon atoms. Examples include a methylenethio group, an ethylenethio group, and a propylenethio group. The diylthio group preferably has 1 to 11 carbon atoms, more preferably 1 to 6 carbon atoms, More preferably, it is 1 to 4, and even more preferably, it is 1 to 3. The alkanediylsulfonyl group is an alkanediylsulfonyl group having 1 to 17 carbon atoms. Examples thereof include a methylene sulfonyl group, an ethylene sulfonyl group, and a propylene sulfonyl group. The number of carbon atoms in the alkanediylsulfonyl group is preferably 1 to 11. It is more preferably 1 to 6, even more preferably 1 to 4, and even more preferably Usually it is 1 to 3. Examples of the cycloalkoxy group include cycloalkoxy groups having 3 to 17 carbon atoms, such as Examples of the cycloalkylalkoxy group include a cyclohexyloxy group and the like. and cycloalkylalkoxy groups having a prime number of 4 to 17, such as cyclohexylmethoxy. The alkoxycarbonyloxy group includes an alkoxy group having 2 to 16 carbon atoms. and oxycarbonyloxy groups, for example, butoxycarbonyloxy groups. The aromatic hydrocarbon group-carbonyloxy group is an aromatic hydrocarbon group having 7 to 17 carbon atoms. Examples of the aromatic group include a carbonyloxy group, such as a benzoyloxy group. The aromatic hydrocarbon group-carbonyl group is an aromatic hydrocarbon group-carbonyl group having 7 to 17 carbon atoms. Examples of aromatic hydrocarbon group-oxy groups include benzoyl groups. Examples of the aryloxy group include aromatic hydrocarbon groups having 6 to 16 carbon atoms and oxy groups, such as phenyloxy. Examples include a silyl group. Haloalkoxy group, haloalkoxycarbonyl group, haloalkylcarbonyl group, haloa The alkylcarbonyloxy group is preferably a haloalkoxy group having 1 to 11 carbon atoms, a haloalkoxy group having 2 to 1 carbon atoms, haloalkoxycarbonyl groups having 1 to 12 carbon atoms, haloalkylcarbonyl groups having 2 to 12 carbon atoms, 2 to 11 haloalkylcarbonyloxy groups, for example, one of the groups exemplified above. Examples of the groups include those in which the hydrogen atoms are replaced with halogen atoms.

[0014] In addition, -CH2- contained in the alicyclic hydrocarbon group may be -O-, -S-, -SO2- or - Examples of the group substituted with CO- include the groups shown below. -O- or -CO- may be replaced by -S- or -SO2-. The bonding site is optional. The position can be: JPEG2026027464000013.jpg46168 -CH2- contained in haloalkyl groups and hydrocarbon groups is -O-, -S-, -SO2- or if replaced by -CO-, the number of carbon atoms before replacement is the total number of carbon atoms in the hydrocarbon group The number may be one, or two or more. R 4 , R 5 , R 6 , R 7 , R 8 and R 9 The hydrocarbon group may have the following substituents: is a halogen atom, a cyano group, an alkyl group having 1 to 12 carbon atoms (including - contained in the alkyl group). CH2- may be replaced by -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. As a substituent, -CH2- contained in the alkyl group is replaced with -O- or -CO-. When the alkyl group is substituted, the number of carbon atoms before substitution is the total number of carbon atoms of the alkyl group. Examples include hydroxy groups, carboxy groups, alkoxy groups, alkoxycarbonyl groups, and alkyl groups. Examples of the alkyl group include an alkylcarbonyl group and an alkylcarbonyloxy group. Alkoxy groups, alkoxycarbonyl groups, alkylcarbonyl groups and alkylcarbonyl groups Examples of the alkoxy group include an alkoxy group having 1 to 11 carbon atoms, an alkoxy group having 2 to 11 carbon atoms, and an alkoxy group having 2 to 11 carbon atoms. alkylcarbonyl groups having 2 to 12 carbon atoms and alkylcarbonyl groups having 2 to 11 carbon atoms. Examples thereof include an nyloxy group, and examples thereof include the same groups as those described above. The hydrocarbon group may have one or more substituents.

[0015] A 1 , A 2 and A 3 Examples of the hydrocarbon group include chain hydrocarbon groups such as alkanediyl groups, Cyclic hydrocarbon groups, aromatic hydrocarbon groups and groups formed by combining these The hydrocarbon group preferably has 2 to 19 carbon atoms, more preferably 2 to 1 8, more preferably 2 to 16, even more preferably 2 to 14, It is more preferably 2 to 12. Examples of the alkanediyl group include a methylene group, an ethylene group, and a propane-1,3-diyl group. Butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group , heptane-1,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,1 2-diyl group, tridecane-1,13-diyl group, tetradecane-1,14-diyl group, Pentadecane-1,15-diyl group, hexadecane-1,16-diyl group and heptadecane linear alkanediyl groups such as alkane-1,17-diyl groups and Ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group group, propane-2,2-diyl group, pentane-2,4-diyl group, 2-methylpropane- 1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group and branched alkanediyl groups such as a 2-methylbutane-1,4-diyl group. The number of carbon atoms in the chain hydrocarbon group is preferably 2 to 18, and more preferably 2 to 12. More preferably, it is 2 to 9, even more preferably, it is 2 to 6, and even more preferably, it is Preferably, it is 2 to 4, and even more preferably, it is 2 or 3.

[0016] The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and may be any of the groups shown below. The binding site can be at any position. JPEG2026027464000014.jpg46168Specifically, cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, Monocyclic cyclohexane-1,4-diyl group, cyclooctane-1,5-diyl group, etc. monocyclic alicyclic hydrocarbon groups, such as alkanediyl groups; Norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane- Polycyclic cycloalkanediyl groups such as 1,5-diyl and adamantane-2,6-diyl groups Examples of suitable hydrocarbon groups include polycyclic and alicyclic hydrocarbon groups represented by the formula: The alicyclic hydrocarbon group preferably has 3 to 18 carbon atoms, more preferably 3 to 16 carbon atoms. It is preferably 3 to 12, and more preferably 3 to 10. Examples of the aromatic hydrocarbon group include a phenylene group, a naphthylene group, an anthrylene group, a biphenyl group, and the like. Examples of aromatic hydrocarbon groups include arylene groups such as phenylene groups and phenanthrylene groups. The aromatic hydrocarbon group preferably has 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, More preferably, it is 6 to 10.

[0017] The group formed by combining an alicyclic hydrocarbon group and an alkanediyl group a group combining an aromatic hydrocarbon group and an alkanediyl group, and an alicyclic Examples of the alicyclic hydrocarbon group include a group in which an alicyclic hydrocarbon group and an aromatic hydrocarbon group are combined. The alkanediyl group in combination with hydrogen and / or aromatic hydrocarbon groups is methyl. In combination, a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, The aromatic hydrocarbon groups may each be a combination of two or more. 4 , R 5 or R 6 may be bonded to a benzene ring to which Examples of the group combining an alicyclic hydrocarbon group and an alkanediyl group include a -divalent Alicyclic hydrocarbon group-alkanediyl group-, -alkanediyl group-divalent alicyclic hydrocarbon group -alkanediyl group-, -alkanediyl group-divalent alicyclic hydrocarbon group-, etc. . Examples of the group combining an aromatic hydrocarbon group and an alkanediyl group include a -divalent Aromatic hydrocarbon group-alkanediyl group-, -alkanediyl group-divalent aromatic hydrocarbon group -alkanediyl group-, -alkanediyl group-divalent aromatic hydrocarbon group-, etc. . Examples of the group combining an alicyclic hydrocarbon group and an aromatic hydrocarbon group include: -aromatic hydrocarbon Group-alicyclic hydrocarbon group-, -alicyclic hydrocarbon group-aromatic hydrocarbon group-, -alicyclic hydrocarbon group, an aromatic hydrocarbon group, an alicyclic hydrocarbon group, and the like.

[0018] A 1 , A 2 and A 3 In this case, only one of the -CH2- in the hydrocarbon group is -O- , -CO-, -S- or -SO2-. One of the -CH2- contained in the hydrocarbon group is -O-, -CO-, -S- or -SO When substituted with 2-, the number of carbon atoms before substitution is regarded as the total number of carbon atoms in the hydrocarbon group. One of the -CH2- contained in the hydrocarbon group is -O-, -CO-, -S- or -SO The group substituted for 2- is a hydroxy group (-CH2- contained in a methyl group is - thiol group (-CH2- in a methyl group is replaced with -S-) substituted), alkoxy group (wherein -CH2- at any position in the alkyl group is replaced by - O-substituted), alkylcarbonyl group (a group at any position in the alkyl group -CH2- is replaced by -CO-), alkylthio group (contained in alkyl group -CH2- at any position is replaced by -S-), alkylsulfonyl group (alkyl a group in which any -CH2- at any position in the alkyl group is replaced with -SO2-), an oxy group (a group in which -CH2- in a methylene group is replaced with -O-), a carbonyl group ( -CH2- in a methylene group is replaced with -CO-), thio group (methylene group -CH2- in the group is replaced with -S-), sulfonyl group (methylene group -CH2- contained in the alkanediyl group is replaced by -SO2-), a group in which any -CH2- at any position in a candiyl group is replaced with -O-), alkanediylcarbonyl group (wherein any -CH2- at any position in the alkanediyl group is - CO-substituted), alkanediylsulfonyl group (a group contained in an alkanediyl group) a group in which any -CH2- at any position is replaced with -SO2-), an alkanediylthio group ( an alkanediyl group in which any -CH2- at any position is replaced with -S-), Cycloalkoxy group, cycloalkylalkoxy group, aromatic hydrocarbon group-carbonyl group, Examples thereof include an aromatic hydrocarbon group-oxy group. The alkoxy group includes an alkoxy group having 1 to 17 carbon atoms, such as methoxy. group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, oxy group octyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, un The alkoxy group preferably has 1 to 11 carbon atoms, and More preferably, it is 1 to 6, even more preferably, it is 1 to 4, and even more preferably, it is 1 ~3. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 18 carbon atoms. Examples include an acetyl group, a propionyl group, and a butyryl group. The number of carbon atoms in the alkyl group is preferably 2 to 12, more preferably 2 to 6, and even more preferably Preferably, it is 2 to 4, and even more preferably, it is 2 or 3. The alkylthio group includes alkylthio groups having 1 to 17 carbon atoms, such as methyl. Examples of the alkylthio group include an alkylthio group, an ethylthio group, a propylthio group, and a butylthio group. The number of carbon atoms in the group is preferably 1 to 11, more preferably 1 to 6, and even more preferably Preferably, it is 1 to 4, and even more preferably 1 to 3. Examples of the alkylsulfonyl group include alkylsulfonyl groups having 1 to 17 carbon atoms. Examples include a methylsulfonyl group, an ethylsulfonyl group, and a propylsulfonyl group. The alkylsulfonyl group preferably has 1 to 11 carbon atoms, more preferably 1 to 11. It is preferably 6, more preferably 1 to 4, and even more preferably 1 to 3. Examples of the alkanediyloxy group include alkanediyloxy groups having 1 to 17 carbon atoms. Examples of such groups include methyleneoxy groups, ethyleneoxy groups, propanediyloxy groups, butanediyloxy groups, and the like. Examples of the carbon atom of the alkanediyloxy group include an alkanediyloxy group and a pentanediyloxy group. The number is preferably 1 to 11, more preferably 1 to 6, and even more preferably 1 to 11. It is 4, and even more preferably 1 to 3. The alkanediylcarbonyl group is an alkanediylcarbonyl group having 2 to 18 carbon atoms. Examples include a methylene carbonyl group, an ethylene carbonyl group, a propanediol group, and the like. Examples thereof include a carbonyl group, a butanediylcarbonyl group, and a pentanediylcarbonyl group. The number of carbon atoms in the alkanediylcarbonyl group is preferably 2 to 12, more preferably 2 Preferably, the number is 1 to 6, more preferably 2 to 4, and even more preferably 2 or 3. The alkanediylsulfonyl group is an alkanediylsulfonyl group having 1 to 17 carbon atoms. Examples thereof include a methylene sulfonyl group, an ethylene sulfonyl group, and a propylene sulfonyl group. The number of carbon atoms in the alkanediylsulfonyl group is preferably 1 to 11. It is more preferably 1 to 6, even more preferably 1 to 4, and even more preferably Usually it is 1 to 3. Examples of the alkanediylthio group include alkanediylthio groups having 1 to 17 carbon atoms. Examples include a methylenethio group, an ethylenethio group, and a propylenethio group. The diylthio group preferably has 1 to 11 carbon atoms, more preferably 1 to 6 carbon atoms, More preferably, it is 1 to 4, and even more preferably, it is 1 to 3. Examples of the cycloalkoxy group include cycloalkoxy groups having 3 to 17 carbon atoms, such as Examples of the cycloalkylalkoxy group include a cyclohexyloxy group and the like. and cycloalkylalkoxy groups having a prime number of 4 to 17, such as cyclohexylmethoxy. The aromatic hydrocarbon group-carbonyl group includes aromatic hydrocarbon groups having 7 to 17 carbon atoms. Aromatic hydrocarbon groups-carbonyl groups, such as benzoyl groups, are examples. Examples of the hydrocarbon group-oxy group include aromatic hydrocarbon group-oxy groups having 6 to 16 carbon atoms. Examples thereof include a phenyloxy group.

[0019] In addition, one of the -CH2- groups contained in the alicyclic hydrocarbon group is -O-, -CO-, or -S Examples of the group substituted with - or -SO2- include the groups shown below. In the group represented, -O- or -CO- may be replaced by -S- or -SO2-. The site can be at any location. JPEG2026027464000015.jpg46168

[0020] A 1 , A 2 and A 3 are each independently a hydrocarbon group having 2 to 20 carbon atoms (the hydrocarbon group One of -CH2- contained in the formula is replaced by -O-, -CO-, -S- or -SO2-. It is preferable that the 1 is *-L 011 -X 01 -L 012 - and A 2 is *-L 021 -X 02 -L 022 - and A 3 is *-L 0 31 -X 03 -L 032 -is (X 01 , X 02 and X 03 are each independently -O -, -CO-, -S- or -SO2-. 011 , L 012, L 021 , L 022 , L 031 and L 032 each independently represents a single bond or a hydrocarbon group having 1 to 19 carbon atoms, However, L 011 and L 012 The total number of carbon atoms is 1 to 19, and L 021 and L 02 2 The total number of carbon atoms is 1 to 19, and L 031 and L 032 The total number of carbon atoms is 1 to 19. * is R 4 , R 5 or R 6 represents the bonding site with the benzene ring to which is more preferred, and A 1 is *-X 01 -L 01 -or*-L 01 -X 01 - and A 2 is *-X 02 -L 02 -or*-L 02 -X 02 - and A 3 is *-X 03 -L 0 3 -or*-L 03 -X 03 -is (X 01 , X 02 and X 03 are each independently, -O-, -CO-, -S- or -SO2-. 01 , L 02 and L 03 Yes, respectively Each independently represents a hydrocarbon group having 1 to 19 carbon atoms. * represents R 4 , R 5 or R 6 can be combined It is more preferable that A represents the bonding site with the benzene ring. 1 , A 2 and A3 -O Preferred are those which have no substituents other than -, -CO-, -S- or -SO2- replacements. I wish. L 011 , L 012 , L 021 , L 022 , L 031 , L 032 , L 01 , L 02 and L 03 The hydrocarbon group having 1 to 19 carbon atoms is a group having 1 to 19 carbon atoms, and 1 , A 2 and A 3 Examples of the groups include the same groups as those listed in the above. X 01 , X 02 and X 03 are each independently preferably -O- or -S-. It is more preferred that it is -O-. A 1 , A 2 and A 3 S + The bond positions to the benzene ring to which each is bonded are independently + The bonding position may be any of o-position, m-position, and p-position relative to the bonding position of If m3 is 1, then A 1 , A 2 and A 3 are each independently, S + For the bonding position of p Preferably, it is bonded at the m-position or m-position, more preferably at the p-position. 1, when m2 and m3 are 2, A 1 , A 2 and A 3 are each independently, S + Bonding position of one is bonded to the o- or m-position, and the other is bonded to the o- or m-position It is preferable that m1, m2 and m3 are 3, and more preferable that two of them are bonded to the m-position. In case A 1 , A 2 and A 3 are each independently, S + Two are at the o-position or are bonded to the m-position, and it is preferred that one is bonded to the p- or m-position, and two are bonded to the m-position. It is more preferred that m1, m2 and m3 are bonded to the same atom at the p-position. In case of 4, A 1 , A 2 and A 3 are each independently, S + For the bonding position of Preferably, two of them are bonded at the p- or m-position, and two of them are bonded at the p- or m-position. It is more preferred that one is bonded to the o-position and two are bonded to the m-position. L 011 , L 012 , L 021 , L 022 , L 031 and L 032 are each independently , a single bond or a hydrocarbon group having 1 to 18 carbon atoms is preferred, It is more preferable that the alkyl group is a hydrocarbon group having 1 to 14 carbon atoms, and a single bond, a chain hydrocarbon group having 1 to 9 carbon atoms, Alicyclic hydrocarbon groups having 3 to 12 carbon atoms or chain hydrocarbon groups having 1 to 4 carbon atoms and chain hydrocarbon groups having 3 to 10 carbon atoms and an alicyclic hydrocarbon group having the following carbon number: It is more preferably a single bond or an alkanediyl group having 1 to 6 carbon atoms. It is even more preferable that it is an alkanediyl group, and it is a single bond or an alkanediyl group having 1 to 3 carbon atoms. A single bond, a methylene group, an ethane-1,1-diyl group is even more preferred. It is more preferably a propane-1,1-diyl group or a propane-2,2-diyl group. However, L 011 and L 012The total number of carbon atoms is 1 to 19, and L 02 1 and L 022 The total number of carbon atoms is 1 to 19, and L 031 and L 032 The total number of carbon atoms is , 1 to 19. L 01 , L 02 and L 03 are each independently a hydrocarbon group having 1 to 18 carbon atoms. It is preferably a hydrocarbon group having 1 to 14 carbon atoms, more preferably a hydrocarbon group having 1 to 9 carbon atoms. A chain hydrocarbon group, an alicyclic hydrocarbon group having 3 to 12 carbon atoms, or a chain hydrocarbon group having 1 to 4 carbon atoms and an alicyclic hydrocarbon group having 3 to 10 carbon atoms, It is more preferably an alkanediyl group having 1 to 6 carbon atoms, and more preferably an alkanediyl group having 1 to 4 carbon atoms. It is even more preferably an alkanediyl group, and more preferably an alkanediyl group having 1 to 3 carbon atoms. and further more preferred are a methylene group, an ethane-1,1-diyl group, a propane-1,1-diyl group, and Even more preferably, it is a diyl group or a propane-2,2-diyl group. m1 is preferably 1, 2, 3 or 4, more preferably 1, 2 or 3. It is preferable that the number is 1 or 2, and it is even more preferable that the number is 1. m2 is preferably 0, 1, 2, 3 or 4, and is preferably 0, 1, 2 or 3. More preferably, it is 0, 1 or 2, and even more preferably, it is 0 or 1. More preferable. m3 is preferably 0, 1, 2, 3 or 4, and is preferably 0, 1, 2 or 3. More preferably, it is 0, 1 or 2, and even more preferably, it is 0 or 1. More preferable. m4 is preferably 1, 2, 3, 4 or 5, and is preferably 1, 2, 3 or 5. More preferably, it is 1, 2 or 3. m5 is preferably 1, 2, 3, 4 or 5, and is preferably 1, 2, 3 or 5. More preferably, it is 1, 2 or 3. m6 is preferably 1, 2, 3, 4 or 5, and is preferably 1, 2, 3 or 5. More preferably, it is 1, 2 or 3. m7 is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2. It is preferable that it is 0 or 1. m8 is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2. It is preferable that it is 0 or 1. m9 is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2. It is preferable that it is 0 or 1. R 4 , R 5 and R 6 are each independently a halogen atom, a fluorinated alkyl group having 1 to 6 carbon atoms, a methyl group or an alkyl group having 1 to 6 carbon atoms (wherein -CH2- contained in the alkyl group is -O- or It is preferable that the alkyl group is a halogen atom, a group having 1 carbon atom, or a group having 1 -CO-. a fluorinated alkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms (wherein the —CH 2- may be replaced by -O- or -CO-. fluorine atom, iodine atom, perfluoroalkyl group having 1 to 4 carbon atoms or alkyl group having 1 to 4 carbon atoms alkyl group (wherein -CH2- in the alkyl group is replaced by -O- or -CO-) It is more preferable that the alkyl group is a fluorine atom, an iodine atom, a hydroxy group, or A trifluoromethyl group is even more preferred. R 4 , R 5 and R 6 The bonding positions of A to the benzene ring are each independently 1 , A 2 and A 3 The bonding position may be any of o-position, m-position, and p-position relative to the bonding position of If m6 is 1, R 4 , R 5 and R 6 are each independently, A 1 , A 2 and A 3 Bonding position of It is preferably bonded to the p-position or m-position relative to the position, and more preferably bonded to the p-position. When m4, m5 and m6 are 2, R 4 , R 5 and R 6 are each independently, A 1 , A 2 and A 3 With respect to the bonding position of , one is bonded to the o-position or m-position, and one is bonded to the p Preferably, the two are bonded to the m-position or m-position, and more preferably, both are bonded to the m-position. If m4, m5 and m6 are 3, then R 4 , R 5 and R 6 are each independently, A 1 , A 2 and A 3 Two are bonded to the o- or m-position, and one is bonded to the p- or m-position. Preferably, two are bonded to the m position and one is bonded to the p position. When m4, m5 and m6 are 4, R 4 , R 5 and R 6 Yes, respectively Independently, A 1 , A 2 and A 3Two of them are bonded to the o- or m-position of the bond. Preferably, two are bonded to the p-position or the m-position, two are bonded to the m-position, and one It is more preferred that one is attached at the o-position and one is attached at the p-position. R 7 , R 8 and R 9 are each independently a halogen atom, a fluorinated alkyl group having 1 to 6 carbon atoms, a methyl group or an alkyl group having 1 to 6 carbon atoms (wherein -CH2- contained in the alkyl group is -O- or It is preferable that the alkyl group is a halogen atom, a group having 1 carbon atom, or a group having 1 -CO-. a fluorinated alkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms (wherein the —CH 2- may be replaced by -O- or -CO-. fluorine atom, iodine atom, perfluoroalkyl group having 1 to 4 carbon atoms or alkyl group having 1 to 4 carbon atoms alkyl group (wherein -CH2- in the alkyl group is replaced by -O- or -CO-) It is more preferable that the alkyl group is a fluorine atom, an iodine atom, a trifluoromethyl atom, or a methyl group. It is even more preferred that the alkyl group is an alkyl, methoxy, methyl or t-butyl group. R 7 , R 8 and R 9 The bonding positions of each of the groups to the benzene ring are independently + At the binding position of In contrast, it may be o-, m- or p-position. Among them, when m7, m8 and m9 are 1, , R 7 , R 8 and R 9 are each independently, S + The bond is at the p- or m-position relative to the bond position of Preferably, m7, m8 and m9 are bonded to each other at the p-position, and more preferably at the p-position. If 9 is 2, R 7 , R 8 and R9 are each independently, S + One for each bond position is preferably bonded to the o- or m-position and one is bonded to the p- or m-position, It is more preferred that one of m7, m8 and m9 be bonded to the m position and one be bonded to the p position. If m9 is 3, R 7 , R 8 and R 9 are each independently, S + For the bonding position of Preferably, two are bonded to the o- or m-position and one is bonded to the p- or m-position. More preferably, two are bonded to the m position and one is bonded to the p position. If 8 and m9 are 4, R 7 , R 8 and R 9 are each independently, S + For the bonding position of Preferably, two are bonded to the o- or m-position, and two are bonded to the p- or m-position. Two are bonded to the m position, one to the o position, and one to the p position. It is more preferable to do so.

[0021] The cation (I) represented by formula (IC) is a cation represented by formula (IC-1). (hereinafter sometimes referred to as "cation (IC-1)"). JPEG2026027464000016.jpg97107 [In formula (IC-1), R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , m1, m2, m3, m4, m5, m6, m7, m8 and m9 have the same meanings as in formula (I). L 1 , L 2 and L 3each independently represents a hydrocarbon group having 1 to 18 carbon atoms. X 1 , X 2 and X 3 each independently represents -O- or -S-.]

[0022] L 1 , L 2 and L 3 The hydrocarbon group having 1 to 18 carbon atoms is a group having 1 to 18 carbon atoms. So, A 1 , A 2 and A 3 Examples of the groups include the same groups as those listed in the above. X 1 is preferably —O—. X 2 is preferably —O—. X 3 is preferably —O—. X 1 , X 2 and X 3 The bonding positions of each of the groups to the benzene ring are independently + At the binding position of In contrast, it may be o-, m- or p-position. Among them, when m1, m2 and m3 are 1, , X 1 , X 2 and X 3 are each independently, S + The bond is at the p- or m-position relative to the bond position of Preferably, m1, m2 and m3 are bonded to each other at the p-position, and more preferably at the p-position. If 3 is 2, then X 1 , X 2 and X 3 are each independently, S + One for each bond position are bonded to the o- or m-position, and one is preferably bonded to the o- or m-position, and 2 It is more preferable that one of m1, m2 and m3 is bonded to the m-position. 1 , X 2 and X 3are each independently, S + Two of them are bonded to the o- or m-position of the bond. Preferably, one of them is bonded to the p-position or the m-position, and two of them are bonded to the m-position. When m1, m2 and m3 are 4, X 1 , X 2 and X 3 are each independently, S + Two are bonded at the o- or m-position relative to the bonding position of Preferably, two of them are bonded to the p-position or m-position, and two of them are bonded to the o-position. It is more preferable that two of them are bonded at the m-position. L 1 , L 2 and L 3 are each independently a hydrocarbon group having 1 to 16 carbon atoms. Preferably, it is a hydrocarbon group having 1 to 14 carbon atoms, and more preferably, it is a chain hydrocarbon group having 1 to 9 carbon atoms. a hydrocarbon group, an alicyclic hydrocarbon group having 3 to 12 carbon atoms or a chain hydrocarbon group having 1 to 4 carbon atoms and a carbon It is more preferable that the group is a group in which an alicyclic hydrocarbon group having 3 to 10 carbon atoms is combined with the alicyclic hydrocarbon group having 3 to 10 carbon atoms. It is more preferably an alkanediyl group having 1 to 6 carbon atoms, and It is even more preferable that the group is an alkanediyl group having 1 to 3 carbon atoms. Among these, a methylene group, an ethane-1,1-diyl group, and a propane-1,1-diyl group are more preferred. It is even more preferred that the aryl group is a group or a propane-2,2-diyl group.

[0023] The cation (I) represented by formula (IC) is a cation represented by formula (IC-2) Also included are cations (hereinafter sometimes referred to as "cations (IC-2)"). JPEG2026027464000017.jpg100107 [In formula (IC-2), R 7, R 8 , R 9 , A 1 , A 2 , A 3 , m1, m2, m3, m7, m8 and m9 are represented by the formula It has the same meaning as (I). R 1 , R 2 and R 3 are each independently a hydrogen atom, a halogen atom, or a group having 1 to 12 carbon atoms. It represents a haloalkyl group or an alkyl group having 1 to 12 carbon atoms, and —CH 2- may be replaced by -O- or -CO-. R 4’ , R 5’ and R 6’ are each independently a halogen atom, a halo having 1 to 12 carbon atoms, It represents an alkyl group or a hydrocarbon group having 1 to 18 carbon atoms, and the hydrocarbon group may have a substituent. The haloalkyl group and the —CH2— contained in the hydrocarbon group are preferably —O—, —S—, — It may be replaced by SO2- or -CO-. m4' represents an integer of 0 to 4, and when m4' is 2 or more, a plurality of R 4’ Mutually They may be the same or different. m5' represents an integer of 0 to 4, and when m5' is 2 or more, a plurality of R 5’ Mutually They may be the same or different. m6' represents an integer of 0 to 4, and when m6' is 2 or more, a plurality of R 6’ Mutually They may be the same or different.]

[0024] R 1 , R 2 and R 3 a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, or a group having 1 to 12 carbon atoms 12 alkyl groups (-CH2- contained in the alkyl group is replaced by -O- or -CO-) It is acceptable to use R 4 ~R 9 Examples of the groups include the same groups as those listed in the above. R 4’ , R 5’ and R 6’ a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, or a A hydrocarbon group having 1 to 18 carbon atoms (the hydrocarbon group may have a substituent, and the haloalkyl group and and -CH2- contained in the hydrocarbon group is replaced by -O-, -S-, -SO2- or -CO-. It may be replaced by R 4 ~R 9 Examples of the groups include the same groups as those listed in the above. R 1 , R 2 and R 3 are each independently a hydrogen atom, a halogen atom, a fluorine atom having 1 to 6 carbon atoms, Fluorinated alkyl group or alkyl group having 1 to 6 carbon atoms (-CH2- contained in the alkyl group is It is preferably a hydrogen atom, a halogen atom, or a halogen atom. a halogen atom, a fluorinated alkyl group having 1 to 4 carbon atoms or an alkyl group having 1 to 4 carbon atoms (the alkyl group -CH2- contained in the alkyl group may be replaced by -O- or -CO-. It is more preferable that the alkyl group is a hydrogen atom, a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms, an alkyl group or an alkyl group having 1 to 4 carbon atoms (wherein —CH2— contained in the alkyl group is —O - or -CO-) is more preferred, and a hydrogen atom, It is more preferable that the group is a fluorine atom, an iodine atom, a hydroxy group, or a trifluoromethyl group. An iodine atom is preferred, and an iodine atom is even more preferred. R 1 , R 2 and R 3 The bonding positions of A to the benzene ring are each independently 1 , A 2 and A 3 The bonding position of R may be either o-position, m-position or p-position. 1 , R 2 and R 3 are each independently, A 1 , A 2 and A 3 Binding to the p- or m-position relative to the binding position of It is preferable that the bond is at the p-position, and more preferable that the bond is at the p-position. m4' is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2. I wish. m5' is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2. I wish. m6' is preferably 0, 1, 2 or 3, more preferably 0, 1 or 2. I wish. R 4’ , R 5’ and R 6’ are each independently a halogen atom, a fluorinated group having 1 to 6 carbon atoms, an alkyl group or an alkyl group having 1 to 6 carbon atoms (wherein —CH2— contained in the alkyl group is —O - or -CO-) is preferred, and a halogen atom, a carbon atom, Fluorinated alkyl groups having 1 to 4 carbon atoms or alkyl groups having 1 to 4 carbon atoms (including alkyl groups -CH2- may be replaced by -O- or -CO-. Preferably, a fluorine atom, an iodine atom, a perfluoroalkyl group having 1 to 4 carbon atoms or a perfluoroalkyl group having 1 to 4 carbon atoms 4 alkyl group (wherein -CH2- in the alkyl group is replaced by -O- or -CO-) It is more preferable that the alkyl group is a fluorine atom, an iodine atom, a hydroxyl atom, or a hydroxyl group. It is even more preferred that the aryl group is a methyl group or a trifluoromethyl group. R 4’ , R 5’ and R 6’The bonding positions of A to the benzene ring are each independently 1 , A 2 and A 3 The bonding position may be any of o-position, m-position, and p-position relative to the bonding position of When m5' and m6' are 1, R 4’ , R 5’ and R 6’ are each independently, A 1 , A 2 and A 3 It is preferable that the bond is at the p-position or m-position relative to the bonding position of When m4', m5' and m6' are 2, R 4’ , R 5’ and R 6’ are each independently, A 1 , A 2 and A 3 For the bonding position of are bonded to the m-position, and it is preferred that one is bonded to the p- or m-position, and two are bonded to the m-position. When m4', m5' and m6' are 3, R 4’ , R 5’ and R 6’ are each independently, A 1 , A 2 and A 3 For the bonding position of Preferably, one is bonded to the p- or m-position, and one is bonded to the p- or m-position. More preferably, two are bonded to the m-position, and two are bonded to the m-position. If m6' is 4, then R 4’ , R 5’ and R 6’ are each independently, A 1 , A 2 and A 3 Two are bonded to the o- or m-position, and two are bonded to the p- or m-position. It is preferred that two are bonded to the o-position and two are bonded to the m-position. More preferable.

[0025] The cation (I) of the salt (I) is represented by the following formulas (Ic-1) to (Ic-64). Examples include cations represented by the following formulas: JPEG2026027464000018.jpg229165

[0026] JPEG2026027464000019.jpg254161

[0027] JPEG2026027464000020.jpg31161

[0028] [Anion (I)] The anion (I) of the salt represented by formula (I) is AI - It is an organic anion represented by the formula: AI - Examples of the organic anion represented by the formula (I) include a sulfonate anion, a sulfonylimide anion, and the like. Examples include anion, sulfonylmethide anion, and carboxylic acid anion. - Represented by The organic anion is preferably a sulfonate anion, and the anion is represented by the formula (IA): It is more preferable that: TIFF2026027464000021.tif2965[In formula (IA), Q 1 and Q 2 are each independently a hydrogen atom, a fluorine atom, or an alkyl group having 1 to 6 carbon atoms. Or it represents a perfluoroalkyl group having 1 to 6 carbon atoms. L 1 represents a saturated hydrocarbon group having 1 to 24 carbon atoms, and —CH 2- may be replaced by -O- or -CO-, and the water contained in the saturated hydrocarbon group The hydrogen atom may be substituted with a fluorine atom or a hydroxy group. Y 1 is a methyl group which may have a substituent or a methyl group having 3 to 4 carbon atoms which may have a substituent. 24 alicyclic hydrocarbon group, and -CH2- contained in the alicyclic hydrocarbon group is -O-, may be replaced by -S-, -SO2- or -CO-.]

[0029] In formula (IA), -CH2- contained in the saturated hydrocarbon group is replaced with -O- or -CO-. When the saturated hydrocarbon group is substituted, the number of carbon atoms before the substitution is the number of carbon atoms of the saturated hydrocarbon group. In the case where -CH2- contained in the alicyclic hydrocarbon group is replaced with -O-, -S-, -SO2- or -CO-, When the alicyclic hydrocarbon group is substituted, the number of carbon atoms before substitution is regarded as the number of carbon atoms of the alicyclic hydrocarbon group.

[0030] Q 1 and Q 2 Examples of the perfluoroalkyl group having 1 to 6 carbon atoms include trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, perfluorosec-butyl group, perfluorotert-butyl group , perfluoropentyl group, and perfluorohexyl group. Q 1 and Q 2 Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, and an isopropyl group. Examples of the butyl group, sec-butyl group, tert-butyl group, pentyl group, and hexyl group are listed. It can be obtained. Q 1 and Q 2 At least one of the groups may contain a fluorine atom or a perfluoroalkyl group. and at least one of them is a fluorine atom or a perfluoroalkyl group. More preferably, each independently is a fluorine atom or a trifluoromethyl group. It is more preferable that both are fluorine atoms.

[0031] L 1 The divalent saturated hydrocarbon group in and monocyclic or polycyclic divalent alicyclic saturated hydrocarbon groups. A group formed by combining two or more of these may also be used. Specifically, methylene group, ethylene group, propane-1,3-diyl group, butane-1,4 -diyl group, pentane-1,5-diyl group, hexane-1,6-diyl group, heptane-1 ,7-diyl group, octane-1,8-diyl group, nonane-1,9-diyl group, decane-1 ,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group, Tridecane-1,13-diyl group, tetradecane-1,14-diyl group, pentadecane- 1,15-diyl group, hexadecane-1,16-diyl group and heptadecane-1,17- linear alkanediyl groups such as diyl groups; Ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group 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 branched alkanediyl groups such as 2-methylbutane-1,4-diyl groups; Cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexa cycloalkanediyl groups such as cyclohexene-1,4-diyl and cyclooctane-1,5-diyl a monocyclic divalent alicyclic saturated hydrocarbon group; Norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane- Polycyclic divalent alicyclic saturated carbons such as 1,5-diyl and adamantane-2,6-diyl groups Examples include a hydrogen group. L 1 The -CH2- contained in the divalent saturated hydrocarbon group represented by the formula: The substituted group may be, for example, a group represented by any one of formulas (b1-1) to (b1-3). In addition, the groups represented by formulae (b1-1) to (b1-3) and their specific examples are In the examples of groups represented by formulae (b1-4) to (b1-11), * and ** represent bonding sites. represents the place, and * represents -Y 1 represents the binding site with

[0032] TIFF2026027464000022.tif26117[In formula (b1-1), L b2 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, A hydrogen atom contained in the group may be substituted with a fluorine atom. L b3 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, The hydrogen atoms contained in the group may be substituted with fluorine atoms or hydroxy groups, and the saturated The -CH2- contained in the hydrocarbon group may be replaced with -O- or -CO-. However, L b2 and L b3 The total number of carbon atoms 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, A hydrogen atom contained in the 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, The hydrogen atoms contained in the group may be substituted with fluorine atoms or hydroxy groups, and the saturated The -CH2- contained in the hydrocarbon group may be replaced 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, A hydrogen atom contained in the 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, The hydrogen atoms contained in the group may be substituted with fluorine atoms or hydroxy groups, and the saturated The -CH2- contained in the hydrocarbon group may be replaced with -O- or -CO-. However, L b6 and L b7 The total number of carbon atoms is 23 or less.

[0033] In the groups represented by formulae (b1-1) to (b1-3), the saturated hydrocarbon group When -CH2- is replaced by -O- or -CO-, the number of carbon atoms before the replacement is The number of carbon atoms in the hydrocarbon group. As the divalent saturated hydrocarbon group, L 1 The divalent saturated hydrocarbon groups are the same as those of do. L b2 is preferably a single bond, a methylene group, *-CH(CF3)-, *-C(CF3) 2-. 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 the divalent saturated hydrocarbon The hydrogen atoms contained in the hydrogen group may be substituted with fluorine atoms. L b5is 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, The hydrogen atoms contained in the hydrocarbon group may be substituted with fluorine atoms. L b7 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, The hydrogen atoms contained in the hydrocarbon group may be substituted with fluorine atoms or hydroxy groups. The —CH2— contained in the divalent saturated hydrocarbon group is replaced with —O— or —CO—. That's fine. L 1 The -CH2- contained in the divalent saturated hydrocarbon group represented by the formula: The substituted group is preferably a group represented by formula (b1-1) or formula (b1-3).

[0034] The group represented by formula (b1-1) includes those represented by formulas (b1-4) to (b1-8), respectively. Examples of such groups include: TIFF2026027464000023.tif48120[In formula (b1-4), L b8 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, A hydrogen atom contained in the 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 the divalent saturated hydrocarbon group The contained -CH2- may be replaced by -O- or -CO-. L b10 represents a single bond or a divalent saturated hydrocarbon group having 1 to 19 carbon atoms, The hydrogen atoms contained in the hydrocarbon group may be substituted with fluorine atoms or hydroxy groups. . However, L b9and L b10 The total number of carbon atoms 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, The hydrogen atoms contained in the hydrocarbon group may be substituted with fluorine atoms or hydroxy groups. . 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, The -CH2- contained in the 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, The hydrogen atoms contained in the hydrocarbon group may be substituted with fluorine atoms or hydroxy groups. . 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, The -CH2- contained in the formula 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, The hydrogen atoms contained in the hydrocarbon group may be substituted with fluorine atoms or hydroxy groups. . However, Lb16 ~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 b10 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 19 carbon atoms, more preferably More preferably, it is 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, more preferably More preferably, it is 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, more preferably More preferably, it is a single bond or a divalent saturated hydrocarbon group having 1 to 4 carbon atoms.

[0035] The group represented by formula (b1-3) is represented by formulas (b1-9) to (b1-11), respectively. Examples include groups represented by the following formula: TIFF2026027464000024.tif23139[In formula (b1-9), L b19represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, A hydrogen atom contained in the group may be substituted with a fluorine atom. L b20 represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, The hydrogen atoms contained in the group are substituted with fluorine atoms, hydroxy groups, or alkylcarbonyloxy groups. The —CH2— contained in the alkylcarbonyloxy group may be replaced by —O—. or -CO-, and the hydrogen contained in the alkylcarbonyloxy group The atom may be substituted with a hydroxy group. However, L b19 and L b20 The total number of carbon atoms is 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, A hydrogen atom contained in the group may be substituted with a fluorine atom. 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, The hydrogen atoms contained in the group are substituted with fluorine atoms, hydroxy groups, or alkylcarbonyloxy groups. The —CH2— contained in the alkylcarbonyloxy group may be replaced by —O—. or -CO-, and the hydrogen contained in the alkylcarbonyloxy group The atom may be substituted with a hydroxy group. However, L b21 , L b22 and L b23 The total number of carbon atoms is 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, A hydrogen atom contained in the group may be substituted with a fluorine atom. L b25 represents a divalent saturated hydrocarbon group having 1 to 21 carbon atoms. L b26 represents a single bond or a divalent saturated hydrocarbon group having 1 to 20 carbon atoms, The hydrogen atoms contained in the group are substituted with fluorine atoms, hydroxy groups, or alkylcarbonyloxy groups. The —CH2— contained in the alkylcarbonyloxy group may be replaced by —O—. or -CO-, and the hydrogen contained in the alkylcarbonyloxy group The atom may be substituted with a hydroxy group. However, L b24 , L b25 and L b26 The total number of carbon atoms is 21 or less. In addition, in the groups represented by formula (b1-9) to formula (b1-11), saturated When a hydrogen atom contained in a mono- or di-hydrocarbon group is substituted with an alkylcarbonyloxy group, The number of carbon atoms before substitution is the number of carbon atoms of the saturated hydrocarbon group. Examples of the alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, a bromide group, and a bromine group. Thyryloxy group, cyclohexylcarbonyloxy group, adamantylcarbonyloxy group etc.

[0036] Examples of the group represented by formula (b1-4) include the following. TIFF2026027464000025.tif17153

[0037] Examples of the group represented by formula (b1-5) include the following. TIFF2026027464000026.tif69163

[0038] Examples of the group represented by formula (b1-6) include the following. TIFF2026027464000027.tif44148

[0039] Examples of the group represented by formula (b1-7) include the following. TIFF2026027464000028.tif62153

[0040] Examples of the group represented by formula (b1-8) include the following. TIFF2026027464000029.tif23146

[0041] Examples of the group represented by formula (b1-2) include the following. TIFF2026027464000030.tif31161

[0042] Examples of the group represented by formula (b1-9) include the following. TIFF2026027464000031.tif43136

[0043] Examples of the group represented by formula (b1-10) include the following. TIFF2026027464000032.tif93165

[0044] Examples of the group represented by formula (b1-11) include the following. TIFF2026027464000033.tif85164

[0045] Y 1 The -CH2- contained in the alicyclic hydrocarbon group represented by the formula Examples of the alicyclic hydrocarbon group not substituted with -CO- include those represented by the formulae (Y1) to (Y2). (Y11), and groups represented by formulae (Y36) to (Y38). Y 1 The -CH2- contained in the alicyclic hydrocarbon group represented by the formula or -CO-, the number may be one or more. As the group, groups represented by formulae (Y12) to (Y35) and formulae (Y39) to (Y43) are The groups represented by formulae (Y12) to (Y35) and (Y39) to (Y43) are -O- or -CO- may be replaced by -S- or -SO2-. * represents L 1 with Represents a binding site. TIFF2026027464000034.tif86167

[0046] Y 1 The alicyclic hydrocarbon group represented by the formula (Y1) to the formula (Y20), the formula (Y26), Formula (Y27), Formula (Y30), Formula (Y31), Formula (Y39) ~ Formula (Y43) and more preferably a group represented by formula (Y11), formula (Y15), or formula (Y1 6), formula (Y20), formula (Y26), formula (Y27), formula (Y30), formula (Y31), formula ( Y39), a group represented by formula (Y40), formula (Y42) or formula (Y43), Preferably, the formula (Y11), the formula (Y15), the formula (Y20), the formula (Y26), the formula (Y27), the formula (Y30), formula (Y31), formula (Y39), formula (Y40), formula (Y42) or formula (Y43 ) is a group represented by the formula: Y 1 The alicyclic hydrocarbon group represented by the formula (Y28) to the formula (Y35), the formula (Y39), the formula ( When the spiro ring is a spiro ring having an oxygen atom, such as the formula (Y40), the formula (Y42) or the formula (Y43), Preferably, the alkanediyl group between the two oxygen atoms has one or more fluorine atoms. In addition, in the alkanediyl group contained in the ketal structure, the methylene adjacent to the oxygen atom Preferably, the group is not substituted with fluorine atoms.

[0047] Y 1 The substituent of the methyl group represented by the formula (I) is a halogen atom, a hydroxyl group, a methyl group having 3 to 4 carbon atoms, or 16 alicyclic hydrocarbon groups, aromatic hydrocarbon groups having 6 to 18 carbon atoms, glycidyloxy groups, - (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, represents an aromatic hydrocarbon group having 6 to 18 carbon atoms or a group in which these groups are combined; The —CH2— contained in the alkyl group and the alicyclic hydrocarbon group represents any one of the integers. -, -SO2- or -CO-, and the alkyl group, the alicyclic hydrocarbon The hydrogen atoms contained in the aromatic hydrocarbon group and the aromatic hydrocarbon group are replaced by hydroxy groups or fluorine atoms. It may be replaced.) Y 1 The substituent of the alicyclic hydrocarbon group represented by the formula (I) is a halogen atom, a hydroxy group, a hydroxyl ... an alkyl group having 1 to 16 carbon atoms which may be substituted with a hydroxy group (the alkyl group -CH2- may be replaced by -O- or -CO-), Alicyclic hydrocarbon groups, aromatic hydrocarbon groups having 6 to 18 carbon atoms, aralkyl groups having 7 to 21 carbon atoms , 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, It represents an alicyclic hydrocarbon group, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these. ja represents an integer of 0 to 4. The alkyl group and the alicyclic hydrocarbon group The -CH2- contained in the alkyl group may be replaced by -O-, -SO2- or -CO-. The hydrogen atoms contained in the alkyl group, the alicyclic hydrocarbon group and the aromatic hydrocarbon group are may be substituted with a silyl group or a fluorine atom.

[0048] Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. do. Examples of the alicyclic hydrocarbon group include a cyclopentyl group, a cyclohexyl group, a methylcyclohexyl group, and a cyclohexyl group. cyclohexyl group, dimethylcyclohexyl group, cycloheptyl group, cyclooctyl group, Examples of the alicyclic hydrocarbon group include a chain hydrocarbon group and a carboxyl group. Examples of the alkyl group include a methylcyclohexyl group and a dimethylcyclohexyl group. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 12, and more preferably 3 to 10. be. Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, and the like. Examples of aromatic hydrocarbon groups include aryl groups such as an alkyl group and a phenanthryl group. It may have a hydrocarbon group or an alicyclic hydrocarbon group, and may have a chain hydrocarbon group having 1 to 18 carbon atoms. Aromatic hydrocarbon groups (tolyl, xylyl, cumenyl, mesityl, p-methyl Phenyl group, p-ethylphenyl group, p-tert-butylphenyl group, 2,6-diethyl phenyl group, 2-methyl-6-ethylphenyl group, etc.), and alicyclic carbons having 3 to 18 carbon atoms Aromatic hydrocarbon groups containing hydrogen hydride groups (p-cyclohexylphenyl group, p-adamantyl The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 14. It is more preferably 6 to 10. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a bromine 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 The alkyl group preferably has 1 to 12 carbon atoms, and more preferably 1 It is preferably 1 to 6, and more preferably 1 to 4. Examples of alkyl groups substituted with hydroxy groups include hydroxymethyl groups, hydroxy Examples include hydroxyalkyl groups such as an ethyl group. Examples of the aralkyl group include a benzyl group, a phenethyl group, a phenylpropyl group, a naphthylmethyl group, and the like. Examples include an ethyl group and a naphthylethyl group. -CH2- in the alkyl group is replaced with -O-, -SO2-, or -CO-, etc. Examples of the group include an alkoxy group, an alkylsulfonyl group, an alkoxycarbonyl group, an alkyl carbonyl group, alkylcarbonyloxy group, or a combination thereof. do. The alkoxy group includes a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, and the like. hydroxyl group, hexyloxy group, heptyloxy group, octyloxy group, decyloxy group and dodecyloxy groups. The number of carbon atoms in the alkoxy group is preferably 1 to 12. It is preferably 1 to 6, and more preferably 1 to 4. Examples of the alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, The number of carbon atoms of the alkylsulfonyl group is preferably 1. The number of carbon atoms 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 and an ethoxycarbonyl group. The number of carbon atoms of the alkoxycarbonyl group is preferably Preferably, it is 2 to 12, more preferably 2 to 6, and further preferably 2 to 4. Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, and a butyryl group. The number of carbon atoms in the alkylcarbonyl group is preferably 2 to 12, and more preferably Preferably, it is 2 to 6, and more preferably, it is 2 to 4. Examples of the alkylcarbonyloxy group include an acetyloxy group and a propionyloxy group. The number of carbon atoms of the alkylcarbonyloxy group is preferably Preferably, it is 2 to 12, more preferably 2 to 6, and further preferably 2 to 4. Examples of the combined group include a group in which an alkoxy group and an alkyl group are combined, a group combining an alkoxy group and an alkoxy group, a group combining an alkoxy group and an alkylcarbonyl group, and a group combining an alkoxy group and an alkylcarbonyloxy group. Examples include: Examples of the group combining an alkoxy group and an alkyl group include a methoxymethyl group, Alkoxyalkyl groups such as methoxyethyl, ethoxyethyl, and ethoxymethyl groups are The number of carbon atoms in the alkoxyalkyl group is preferably 2 to 12, and more preferably It is preferably 2 to 6, and more preferably 2 to 4. Examples of the group combining an alkoxy group and an alkoxy group include a methoxymethoxy group, a methoxy group, a methyl ... alkoxyalkoxy groups such as ethoxyethoxy, ethoxymethoxy, and ethoxyethoxy groups The number of carbon atoms in the alkoxyalkoxy group is preferably 2 to 12, and more preferably Preferably, it is 2 to 6, and more preferably, it is 2 to 4. Examples of a group combining an alkoxy group and an alkylcarbonyl group include methoxyacetyl Alkoxy groups such as methoxypropionyl groups, ethoxyacetyl groups, and ethoxypropionyl groups The number of carbon atoms in the alkoxyalkylcarbonyl group is Preferably, it is 3 to 13, more preferably 3 to 7, and even more preferably 3 to 5. be. Examples of the group combining an alkoxy group and an alkylcarbonyloxy group include methoxy groups. Cetyloxy group, methoxypropionyloxy group, ethoxyacetyloxy group, ethoxy Examples include alkoxyalkylcarbonyloxy groups such as propionyloxy groups. The number of carbon atoms in the oxyalkylcarbonyloxy group is preferably 3 to 13, more preferably It is preferably 3 to 7, and more preferably 3 to 5. -CH2- contained in the alicyclic hydrocarbon group is replaced by -O-, -SO2-, -CO-, etc. The groups represented by formula (Y12) to formula (Y35) and formula (Y39) to formula (Y43) are Examples of such groups include:

[0049] Y 1 is preferably an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent. More preferably, it is an alicyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent. and more preferably an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent. and more preferably an adamantyl group which may have a substituent. A hydrogen group or -CH2- constituting an adamantyl group is replaced with -O-, -SO2- or -CO-. Specifically, the following may be mentioned: JPEG2026027464000035.jpg117158

[0050] JPEG2026027464000036.jpg54155

[0051] Among these, an adamantyl group, a hydroxyadamantyl group, an oxoadamantyl group, and the like are preferable. a group represented by the formula (Y42), the formula (Y100) to the formula (Y114), the formula (Y134) to the formula (Y13 9), and particularly preferred are hydroxyadamantyl groups, oxoadamantyl groups, a methyl group, a group containing the same, or a group represented by the formula (Y42), the formula (Y100) to the formula (Y114), the formula (Y1 34) to a group represented by formula (Y139).

[0052] The anion represented by formula (IA) includes the anions represented by formulas (IA-1) to (IA-61). The anion represented by the formula (hereinafter, it may be referred to as "anion (IA-1)" or the like depending on the formula number) Formula (IA-1) to Formula (IA-4), Formula (IA-9), Formula (I- A-10), formula (IA-24) to formula (IA-33), formula (IA-36) to formula (I- A-40), an anion represented by any one of formulas (IA-47) to (IA-61) More preferable. TIFF2026027464000037.tif80143

[0053] TIFF2026027464000038.tif95154

[0054] TIFF2026027464000039.tif122161

[0055] TIFF2026027464000040.tif90156

[0056] TIFF2026027464000041.tif147151

[0057] JPEG2026027464000042.jpg97163

[0058] where R i2 ~R i7 are each independently, for example, an alkyl group having 1 to 4 carbon atoms, preferably R is a methyl group or an ethyl group. i8 is, for example, a chain hydrocarbon having 1 to 12 carbon atoms. a group, 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 is more preferred, and a methyl group, an ethyl group, a cyclohexyl group, It is a silyl group or an adamantyl group. A41 is a single bond or an alkanediyl group having 1 to 4 carbon atoms. Q is a 1 and Q 2 has the same meaning as above. Specific examples of the anion represented by formula (IA) include those described in JP 2010-204646 A Examples of anions include those described in the publication No.

[0059] The anion represented by formula (IA) is preferably an anion represented by formula (Ia-1) to formula (Ia- 40) are examples of anions represented by the formula: TIFF2026027464000043.tif89154

[0060] TIFF2026027464000044.tif75144

[0061] TIFF2026027464000045.tif141167

[0062] TIFF2026027464000046.tif109165

[0063] JPEG2026027464000047.jpg28117

[0064] Among them, the compounds represented by formula (Ia-1) to formula (Ia-4), formula (Ia-7) to formula (Ia-1 1), formula (Ia-14) to formula (Ia-30) and formula (Ia-35) to formula (Ia- 40) is preferred.

[0065] AI - Examples of the sulfonylimide anion represented by the formula (I) include the following. TIFF2026027464000048.tif36136

[0066] Examples of sulfonylmethide anions include the following: TIFF2026027464000049.tif30128

[0067] Examples of carboxylate anions include the following: TIFF2026027464000050.tif46168

[0068] Specific examples of the salt (I) include salts of any combination of the above-mentioned cations and anions. Specific examples of the salt (I) are shown in the table below. In the table below, each symbol represents the symbol attached to the structure representing the above-mentioned anion or cation. "~" indicates that the salt (I) corresponds to the anion (I) or the cation (I), respectively. For example, the salt (I-1) is a compound obtained by combining an anion represented by formula (Ia-1) and a compound represented by formula (Ic -1), and the salt (I-2) is a salt represented by the formula (Ia-2) The salt (I-39) consisting of an anion and a cation represented by formula (Ic-1) is represented by formula ( A salt consisting of an anion represented by formula (Ia-1) and a cation represented by formula (Ic-2) The salt (I-2433) is a compound obtained by combining an anion represented by formula (Ia-39) and a compound represented by formula (I- and a cation represented by formula (Ia-39), salt (I-2434) is and a cation represented by formula (Ic-2), a salt (I-24 97) is a compound obtained by reacting an anion represented by formula (Ia-40) with a cation represented by formula (Ic-1) This indicates a salt consisting of TIFF2026027464000051.tif28112 [Table 1] TIFF2026027464000053.tif151158

[0069] Among these, the salt (I) is represented by the formula (Ia-1) to the formula (Ia-4), the formula (Ia-7) to the formula (Ia-8), Ia-11), formula (Ia-14) to formula (Ia-30) and formula (Ia-35) to formula (Ia-40) and an anion represented by any one of formulas (Ic-1) to (Ic-64) ) is preferably a salt in which a cation represented by any one of the following is combined: 1) ~ Salt (I-4), Salt (I-7) ~ Salt (I-11), Salt (I-14) ~ Salt (I-30) , Salt (I-35) ~ Salt (I-38), Salt (I-39) ~ Salt (I-42), Salt (I-45) ~Salt (I-49), Salt (I-52) ~Salt (I-68), Salt (I-73) ~Salt (I-76) , Salt (I-77) ~ Salt (I-80), Salt (I-83) ~ Salt (I-87), Salt (I-90) ~ Salt (I-106), Salt (I-111) ~ Salt (I-114), Salt (I-115) ~ Salt (I -118), Salt (I-121) ~ Salt (I-125), Salt (I-128) ~ Salt (I-144 ), salt (I-149) ~ salt (I-152), salt (I-153) ~ salt (I-156), salt ( I-159) ~ Salt (I-163), Salt (I-166) ~ Salt (I-182), Salt (I-18 7) ~ Salt (I-190), Salt (I-191) ~ Salt (I-194), Salt (I-197) ~ Salt (I-201), Salt (I-204) ~ Salt (I-220), Salt (I-225) ~ Salt (I-2 28), Salt (I-229) ~ Salt (I-232), Salt (I-235) ~ Salt (I-239), Salt (I-242) ~ Salt (I-258), Salt (I-263) ~ Salt (I-266), Salt (I- 267) ~ Salt (I-270), Salt (I-273) ~ Salt (I-277), Salt (I-280) ~Salt (I-296), Salt (I-301) ~Salt (I-304), Salt (I-305) ~Salt (I -308), Salt (I-311) ~ Salt (I-315), Salt (I-318) ~ Salt (I-334 ), salt (I-339) ~ salt (I-342), salt (I-343) ~ salt (I-346), salt ( I-349) ~ Salt (I-353), Salt (I-356) ~ Salt (I-372), Salt (I-37 7) ~ Salt (I-380), Salt (I-381) ~ Salt (I-384), Salt (I-387) ~ Salt (I-391), Salt (I-394) ~ Salt (I-410), Salt (I-415) ~ Salt (I-4 18), Salt (I-419) ~ Salt (I-422), Salt (I-425) ~ Salt (I-429), Salt (I-432) ~ Salt (I-448), Salt (I-453) ~ Salt (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-524 ), 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-56 7) ~ 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-6 08), 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-75 7) ~ Salt (I-760), Salt (I-761) ~ Salt (I-764), Salt (I-767) ~ Salt (I-771), salt (I-774) ~ salt (I-790), salt (I-795) ~ salt (I-7 98), 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-94 7) ~ Salt (I-950), Salt (I-951) ~ Salt (I-954), Salt (I-957) ~ Salt (I-961), Salt (I-964) ~ Salt (I-980), Salt (I-985) ~ Salt (I-9 88), Salt (I-989) ~ Salt (I-992), Salt (I-995) ~ Salt (I-999), Salt (I-1002) ~ Salt (I-1018), Salt (I-1023) ~ Salt (I-1026), Salt (I-1027) ~ Salt (I-1030), Salt (I-1033) ~ Salt (I-1037), Salt (I-1040) ~ Salt (I-1056), Salt (I-1061) ~ Salt (I-1064), Salt (I-1065) ~ Salt (I-1068), Salt (I-1071) ~ Salt (I-1075), Salt (I-1078) ~ Salt (I-1094), Salt (I-1099) ~ Salt (I-1102), Salt (I-1103) ~ Salt (I-1106), Salt (I-1109) ~ Salt (I-1113), Salt (I-1116) ~ Salt (I-1132), Salt (I-1137) ~ Salt (I-1140), Salt (I-1141) ~ Salt (I-1144), Salt (I-1147) ~ Salt (I-1151), Salt (I-1154) ~ Salt (I-1170), Salt (I-1175) ~ Salt (I-1178), Salt (I-1179) ~ Salt (I-1182), Salt (I-1185) ~ Salt (I-1189), Salt (I-1192) ~ Salt (I-1208), Salt (I-1213) ~ Salt (I-1216), Salt (I-1217) ~ Salt (I-1220), Salt (I-1223) ~ Salt (I-1227), Salt (I-1230) ~ Salt (I-1246), Salt (I-1251) ~ Salt (I-1254), Salt (I-1255) ~ Salt (I-1258), Salt (I-1261) ~ Salt (I-1265), Salt (I-1268) ~ Salt (I-1284), Salt (I-1289) ~ Salt (I-1292), Salt (I-1293) ~ Salt (I-1296), Salt (I-1299) ~ Salt (I-1303), Salt (I-1306) ~ Salt (I-1322), Salt (I-1327) ~ Salt (I-1330), Salt (I-1331) ~ Salt (I-1334), Salt (I-1337) ~ Salt (I-1341), Salt (I-1344) ~ Salt (I-1360), Salt (I-1365) ~ Salt (I-1368), Salt (I-1369) ~ Salt (I-1372), Salt (I-1375) ~ Salt (I-1379), Salt (I-1382) ~ Salt (I-1398), Salt (I-1403) ~ Salt (I-1406), Salt (I-1407) ~ Salt (I-1410), Salt (I-1413) ~ Salt (I-1417), Salt (I-1420) ~ Salt (I-1436), Salt (I-1441) ~ Salt (I-1444), Salt (I-1445) ~ Salt (I-1448), Salt (I-1451) ~ Salt (I-1455), Salt (I-1458) ~ Salt (I-1474), Salt (I-1479) ~ Salt (I-1482), Salt (I-1483) ~ Salt (I-1486), Salt (I-1489) ~ Salt (I-1493), Salt (I-1496) ~ Salt (I-1512), Salt (I-1517) ~ Salt (I-1520), Salt (I-1521) ~ Salt (I-1524), Salt (I-1527) ~ Salt (I-1531), Salt (I-1534) ~ Salt (I-1550), Salt (I-1555) ~ Salt (I-1558), Salt (I-1559) ~ Salt (I-1562), Salt (I-1565) ~ Salt (I-1569), Salt (I-1572) ~ Salt (I-1588), Salt (I-1593) ~ Salt (I-1596), Salt (I-1597) ~ Salt (I-1600), Salt (I-1603) ~ Salt (I-1607), Salt (I-1610) ~ Salt (I-1626), Salt (I-1631) ~ Salt (I-1634), Salt (I-1635) ~ Salt (I-1638), Salt (I-1641) ~ Salt (I-1645), Salt (I-1648) ~ Salt (I-1664), Salt (I-1669) ~ Salt (I-1672), Salt (I-1673) ~ Salt (I-1676), Salt (I-1679) ~ Salt (I-1683), Salt (I-1686) ~ Salt (I-1702), Salt (I-1707) ~ Salt (I-1710), Salt (I-1711) ~ Salt (I-1714), Salt (I-1717) ~ Salt (I-1721), Salt (I-1724) ~ Salt (I-1740), Salt (I-1745) ~ Salt (I-1748), Salt (I-1749) ~ Salt (I-1752), Salt (I-1755) ~ Salt (I-1759), Salt (I-1762) ~ Salt (I-1778), Salt (I-1783) ~ Salt (I-1786), Salt (I-1787) ~ Salt (I-1790), Salt (I-1793) ~ Salt (I-1797), Salt (I-1800) ~ Salt (I-1816), Salt (I-1821) ~ Salt (I-1824), Salt (I-1825) ~ Salt (I-1828), Salt (I-1831) ~ Salt (I-1835), Salt (I-1838) ~ Salt (I-1854), Salt (I-1859) ~ Salt (I-1862), Salt (I-1863) ~ Salt (I-1866), Salt (I-1869) ~ Salt (I-1873), Salt (I-1876) ~ Salt (I-1892), Salt (I-1897) ~ Salt (I-1900), Salt (I-1901) ~ Salt (I-1904), Salt (I-1907) ~ Salt (I-1911), Salt (I-1914) ~ Salt (I-1930), Salt (I-1935) ~ Salt (I-1938), Salt (I-1939) ~ Salt (I-1942), Salt (I-1945) ~ Salt (I-1949), Salt (I-1952) ~ Salt (I-1968), Salt (I-1973) ~ Salt (I-1976), Salt (I-1977) ~ Salt (I-1980), Salt (I-1983) ~ Salt (I-1987), Salt (I-1990) ~ Salt (I-2006), Salt (I-2011) ~ Salt (I-2014), Salt (I-2015) ~ Salt (I-2018), Salt (I-2021) ~ Salt (I-2025), Salt (I-2028) ~ Salt (I-2044), Salt (I-2049) ~ Salt (I-2052), Salt (I-2053) ~ Salt (I-2056), Salt (I-2059) ~ Salt (I-2063), Salt (I-2066) ~ Salt (I-2082), Salt (I-2087) ~ Salt (I-2090), Salt (I-2091) ~ Salt (I-2094), Salt (I-2097) ~ Salt (I-2101), Salt (I-2104) ~ Salt (I-2120), Salt (I-2125) ~ Salt (I-2128), Salt (I-2129) ~ Salt (I-2132), Salt (I-2135) ~ Salt (I-2139), Salt (I-2142) ~ Salt (I-2158), Salt (I-2163) ~ Salt (I-2166), Salt (I-2167) ~ Salt (I-2170), Salt (I-2173) ~ Salt (I-2177), Salt (I-2180) ~ Salt (I-2196), Salt (I-2201) ~ Salt (I-2204), Salt (I-2205) ~ Salt (I-2208), Salt (I-2211) ~ Salt (I-2215), Salt (I-2218) ~ Salt (I-2234), Salt (I-2239) ~ Salt (I-2242), Salt (I-2243) ~ Salt (I-2246), Salt (I-2249) ~ Salt (I-2253), Salt (I-2256) ~ Salt (I-2272), Salt (I-2277) ~ Salt (I-2280), Salt (I-2281) ~ Salt (I-2284), Salt (I-2287) ~ Salt (I-2291), Salt (I-2294) ~ Salt (I-2310), Salt (I-2315) ~ Salt (I-2318), Salt (I-2319) ~ Salt (I-2322), Salt (I-2325) ~ Salt (I-2329), Salt (I-2332) ~ Salt (I-2348), Salt (I-2353) ~ Salt (I-2356), Salt (I-2357) ~ Salt (I-2360), Salt (I-2363) ~ Salt (I-2367), Salt (I-2370) ~ Salt (I-2386), Salt (I-2391) ~ Salt (I-2394), Salt (I-2395) ~ Salt (I-2398), Salt (I-2401) ~ Salt (I-2405), Salt (I-2408) ~ Salt (I-2424), Salt (I-2429) ~ Salt (I-2432), Salt (I-2433) to Salt (I-2560) are preferred.

[0070] <Method for producing salt (I)> The salt (I) can be prepared by dissolving a salt represented by formula (Ia) and a salt represented by formula (Ib) in a solvent. It can be produced by reacting JPEG2026027464000054.jpg105165 [wherein all symbols have the same meanings as above. R A , R B and R C Yes, respectively Each independently represents a hydrocarbon group having 1 to 12 carbon atoms, or R A , R B and R C together R may form an aromatic ring. D represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms. ] Examples of solvents include chloroform, monochlorobenzene, acetonitrile, and water. can be. The reaction temperature is usually 15° C. to 80° C., and the reaction time is usually 0.5 to 24 hours.

[0071] Examples of the salt represented by formula (Ib) include salts represented by the following formula: The methods described in JP 2011-116747 A and JP 2016-047815 A It can be easily produced by a method similar to that described above or by a known method. JPEG2026027464000055.jpg199161

[0072] The salt represented by formula (Ia) is a salt represented by formula (Ic) and a salt represented by formula (I-d1). a compound represented by formula (I-d1), a compound represented by formula (I-d2), and a compound represented by formula (I-d3) The compound can be produced by reacting the compound with potassium carbonate in a solvent. JPEG2026027464000056.jpg98167 [wherein all symbols have the same meanings as defined above.] Examples of solvents include chloroform, monochlorobenzene, acetonitrile, and water. can be. 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 (Ic) include the salt represented by the following formula, which is readily available on the market. can be obtained at. JPEG2026027464000057.jpg36163

[0074] A compound represented by formula (I-d1), a compound represented by formula (I-d2), and a compound represented by formula (I-d3) ) includes the compounds shown below, which are readily available on the market. It is possible. JPEG2026027464000058.jpg41165

[0075] <Acid generator> The acid generator of the present invention is an acid generator containing one kind of salt (I). Alternatively, two or more types of salt (I) may be contained. In addition to the salt (I), the acid generator of the present invention may also include acid generators known in the resist field (hereinafter referred to as "acid generators"). The acid generator (B) may be used alone. Alternatively, two or more of them may be used in combination.

[0076] The acid generator (B) may be either a nonionic or ionic acid generator. Biocides include sulfonate esters (e.g., 2-nitrobenzyl esters, aromatic sulfonates, etc.). sulfonates, oximesulfonates, N-sulfonyloxyimides, sulfonyloxyketones ton, diazonaphthoquinone 4-sulfonate), sulfones (e.g., disulfones, ketones Examples of ionic acid generators include ionic acid generators such as ionic acid generators (sulfones, sulfonyldiazomethanes, etc.). Onium salts containing ammonium cations (e.g., diazonium salts, phosphonium salts, sulfonium salts) Typical examples of onium salts include sulfonate anions. anion, sulfonylimide anion, sulfonylmethide anion, etc.

[0077] Examples of the acid generator (B) include those disclosed in JP-A-63-26653 and JP-A-55-164824; JP-A-62-69263, JP-A-63-146038, JP-A-63-163452 , JP 62-153853 A, JP 63-146029 A, U.S. Pat. No. 3,779, 778, U.S. Pat. No. 3,849,137, German Patent No. 3914407, European Patent No. Compounds that generate acids when exposed to radiation, such as those described in US Pat. No. 126,712, can be used. In addition, compounds produced by known methods may be used. The acid generator (B) may be a mixture of two or more compounds. They may also be used in combination.

[0078] The acid generator (B) is preferably a salt represented by formula (B1) (hereinafter referred to as "acid generator (B1)"). However, this does not include salt (I). TIFF2026027464000059.tif2962[In formula (B1), Q b1 and Q b2are each independently a hydrogen atom, a fluorine atom, an alkyl group having 1 to 6 carbon atoms, It represents a fluoroalkyl group 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 the divalent saturated hydrocarbon group The contained —CH2— may be replaced by —O— or —CO—, and the divalent saturated carbon The hydrogen atoms contained in the hydrogen hydride group may be substituted with fluorine atoms or hydroxy groups. Y is a methyl group which may have a substituent or a methyl group having 3 to 2 carbon atoms which may have a substituent. 4, and -CH2- contained in the alicyclic hydrocarbon group is -O-, - It may be replaced by -S-, -SO2- or -CO-. Z1 + represents an organic cation.

[0079] Q in formula (B1) b1 , Q b2 , L b1 and Y are the groups in the above formula (IA), respectively. RuQ 1 , Q 2 , L 1 and Y 1 And similar things can be mentioned. The sulfonate anion in formula (B1) may be an anion represented by formula (IA) Similar examples include:

[0080] Z1 + Examples of the organic cation include organic onium cations, organic sulfonium cations, Organic iodonium cations, organic ammonium cations, benzothiazolium cations, and Among these, organic sulfonium cations are Preferred are iodonium and organic iodonium cations, and more preferred are arylsulfonium cations. Specifically, the cation represented by any one of formulas (b2-1) to (b2-4) (hereinafter Below, depending on the formula number, it may be called "cation (b2-1)" etc.).

[0081] TIFF2026027464000060.tif46169In equations (b2-1) to (b2-4), R b4 ~R b6 are each independently a chain hydrocarbon group having 1 to 30 carbon atoms, a chain hydrocarbon group having 3 to 36 carbon atoms, It represents an alicyclic hydrocarbon group or an aromatic hydrocarbon group having 6 to 36 carbon atoms, and the chain hydrocarbon group The hydrogen atoms contained in the alkyl group are hydroxyl groups, alkoxy groups with 1 to 12 carbon atoms, and alkyl groups with 3 to 12 carbon atoms. It may be substituted with a cyclic hydrocarbon group or an aromatic hydrocarbon group having 6 to 18 carbon atoms, The hydrogen atoms contained in the hydrocarbon group are halogen atoms, aliphatic hydrocarbon groups having 1 to 18 carbon atoms, may be substituted with an alkylcarbonyl group having 2 to 4 carbon atoms or a glycidyloxy group. The hydrogen atoms contained in the aromatic hydrocarbon group are substituted with halogen atoms, hydroxy groups, and groups having 1 to 10 carbon atoms. aliphatic hydrocarbon groups of 18, fluorinated alkyl groups of 1 to 12 carbon atoms or alkyl groups of 1 to 12 carbon atoms It may be substituted with a koxy group. R b4 and R b5 are bonded to each other and form a ring with the sulfur atom to which they are attached. -CH2- contained in the ring may be replaced by -O-, -S- or -CO-. good. R b7 and R b8 are each independently a halogen atom, a hydroxyl group, a fatty acid having 1 to 12 carbon atoms, Aliphatic hydrocarbon group, fluorinated alkyl group having 1 to 12 carbon atoms, or alkoxy group having 1 to 12 carbon atoms Represents. 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, R in Numbers b8 may be the same or different. R b9 and R b10 are each independently a chain hydrocarbon group having 1 to 36 carbon atoms or a chain hydrocarbon group having 3 to 4 carbon atoms, Represents 36 alicyclic hydrocarbon groups. R b9 and R b10 are bonded to each other and form a ring with the sulfur atom to which they are attached -CH2- contained in the ring may be replaced by -O-, -S- or -CO-. Good too. R b11 is a hydrogen atom, a chain hydrocarbon group having 1 to 36 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms, It represents a hydrogen group or an aromatic hydrocarbon group having 6 to 18 carbon atoms. R b12 represents a chain hydrocarbon group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, or It represents an aromatic hydrocarbon group having 6 to 18 carbon atoms, and the hydrogen atoms contained in the chain hydrocarbon group are It may be substituted with an aromatic hydrocarbon group having 6 to 18 prime numbers, and the aromatic hydrocarbon group The hydrogen atom is preferably an alkoxy group having 1 to 12 carbon atoms or an alkylcarbonyl group having 1 to 12 carbon atoms. It may be substituted with an oxy group. R b11 and R b12 are bonded to each other to form a ring including the -CH-CO- to which they are attached. -CH2- contained in the ring may be replaced by -O-, -S- or -CO-. It is also possible. R b13 ~R b18 are each independently a halogen atom, a hydroxyl group, a fatty acid having 1 to 12 carbon atoms, Aliphatic hydrocarbon group, fluorinated alkyl group having 1 to 12 carbon atoms, or alkoxy group having 1 to 12 carbon atoms Represents. Rb13 and R b14 are sulfur atoms bonded together with the benzene rings to which they are attached. A ring containing —CH2— may be formed, and —CH2— contained in the ring may be —O—, —S— or —CO—. - may be replaced with L b31 represents a sulfur atom or an oxygen atom. o2, p2, s2, and t2 each independently represent an integer of 0 to 5. q2 and r2 each independently represent an integer of 0 to 4; u2 represents 0 or 1. When o2 is 2 or more, multiple R b13 are the same or different, and when p2 is 2 or more, multiple R b14 are the same or different, and when q2 is 2 or more, multiple R b15 are the same or different, r2 When is 2 or more, multiple R b16 are the same or different, and when s2 is 2 or more, multiple R b17 teeth Identical or different, when t2 is 2 or more, multiple R b18 are the same or different. When u2 is 0, any one of o2, p2, q2, and r2 is 1 or more, and R b1 3 ~R b16 At least one of these is preferably a halogen atom, and when u2 is 1, , o2, p2, s2, t2, q2, and r2 are 1 or more, and R b13 ~ R b18 At least one of these is preferably a halogen atom. Furthermore, when u2 is 0, r2 is preferably 1 or more, and 1 is even more preferable. In addition, when u2 is 0 and r2 is 1 or more, R b16 is a halogen atom It is preferable. The aliphatic hydrocarbon group refers to a chain hydrocarbon group and an alicyclic hydrocarbon group. Examples of the chain hydrocarbon group include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group. group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, octyl group and An example of an alkyl group is a 2-ethylhexyl group. In particular, R b9 ~R b12 The chain hydrocarbon group preferably has 1 to 12 carbon atoms. The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and a monocyclic alicyclic hydrocarbon group may be Examples of the hydrogen group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. cycloalkyl groups such as cyclohexyl, cycloheptyl, cyclooctyl, and cyclodecyl groups. Examples of polycyclic alicyclic hydrocarbon groups include decahydronaphthyl and adamantyl groups. , norbornyl group, and the following groups. TIFF2026027464000061.tif10158 In particular, R b9 ~R b12 The alicyclic hydrocarbon group preferably has 3 to 18 carbon atoms, more preferably has 4 to 12 carbon atoms. Examples of alicyclic hydrocarbon groups in which hydrogen atoms are substituted with aliphatic hydrocarbon groups include methylcyclohexane. cyclohexyl group, dimethylcyclohexyl group, 2-methyladamantan-2-yl group, 2-ethyl 2-Isopropyladamantan-2-yl group, methylnor Examples of the alkyl group include a bornyl group and an isobornyl group. In the alicyclic hydrocarbon group, the total number of carbon atoms in the alicyclic hydrocarbon group and the aliphatic hydrocarbon group is preferably 1. Preferably it is 20 or less. The fluorinated alkyl group refers to an alkyl group having 1 to 12 carbon atoms and a fluorine atom. fluoromethyl group, difluoromethyl group, trifluoromethyl group, perfluorobutyl group, etc. The number of carbon atoms in the fluorinated alkyl group is preferably 1 to 9, and more preferably 1. It is preferably 1 to 6, and more preferably 1 to 4.

[0082] Examples of the aromatic hydrocarbon group include a phenyl group, a biphenyl group, a naphthyl group, and a phenanthryl group. The aromatic hydrocarbon group may be a chain hydrocarbon group or an alicyclic hydrocarbon group. It may have a substituted or unsubstituted alkyl group, and may have an aromatic hydrocarbon group ( 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 aromatic hydrocarbon groups having alicyclic hydrocarbon groups with 3 to 18 carbon atoms (p-cyclohexane, etc.) Examples of aromatic carbons include phenyl groups, p-adamantylphenyl groups, etc. When the hydrogen group has a chain hydrocarbon group or an alicyclic hydrocarbon group, the chain hydrocarbon group has 1 to 18 carbon atoms. Hydrocarbon groups and alicyclic hydrocarbon groups having 3 to 18 carbon atoms are preferred. Examples of aromatic hydrocarbon groups in which hydrogen atoms are substituted with alkoxy groups include p-methoxyphenyl. Examples thereof include a methyl group. Examples of the chain hydrocarbon group in which a hydrogen atom is substituted with an aromatic hydrocarbon group include a benzyl group, a phenyl group, and a phenyl group. ethyl group, phenylpropyl group, trityl group, naphthylmethyl group, naphthylethyl group, etc. Examples include aralkyl groups. The alkoxy group includes a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, and the like. hydroxyl group, hexyloxy group, heptyloxy group, octyloxy group, decyloxy group and dodecyloxy groups. Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, and a butyryl group. can be done. Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. do. Examples of the alkylcarbonyloxy group include a methylcarbonyloxy group and an ethylcarbonyloxy group. Oxy group, propylcarbonyloxy group, isopropylcarbonyloxy group, butylcarbonyloxy group butylcarbonyloxy group, sec-butylcarbonyloxy group, tert-butylcarbonyloxy group silyl group, pentylcarbonyloxy group, hexylcarbonyloxy group, octylcarbonyl Examples include an oxy group and a 2-ethylhexylcarbonyloxy group. R b4 and R b5 and bond together with the sulfur atom to which they are attached to form a ring The ring may be monocyclic, polycyclic, aromatic, non-aromatic, saturated or unsaturated. The ring may have 3 to 18 carbon atoms, and preferably has 4 to 18 carbon atoms. The ring containing a sulfur atom may be a 3- to 12-membered ring, preferably a 3- to 7-membered ring. Examples include the rings shown below, where * represents a binding site. TIFF2026027464000062.tif23143R b9 and R b10 The ring formed by combining and can be monocyclic, polycyclic, aromatic, or non-aromatic. The ring may be either saturated or unsaturated. Examples of the ring include a 3-membered ring to a 12-membered ring. Preferably, it is a 3- to 7-membered ring. For example, a thiolan-1-ium ring (tetrahydrothio) thiophenium ring), thian-1-ium ring, 1,4-oxathian-4-ium ring, etc. It can be obtained. R b11 and R b12The ring formed by combining and can be monocyclic, polycyclic, aromatic, or non-aromatic. The ring may be either saturated or unsaturated. Examples of the ring include a 3-membered ring to a 12-membered ring. and preferably a 3- to 7-membered ring. Oxocycloheptane ring, oxocyclohexane ring , oxonorbornane ring, oxoadamantane ring, etc.

[0083] Among the cations (b2-1) to (b2-4), the cation (b2 -1). Examples of the cation (b2-1) include the following cations. TIFF2026027464000063.tif80158

[0084] TIFF2026027464000064.tif110165

[0085] Examples of the cation (b2-2) include the following cations. TIFF2026027464000065.tif18150

[0086] Examples of the cation (b2-3) include the following cations. TIFF2026027464000066.tif24126

[0087] Examples of the cation (b2-4) include the following cations. JPEG2026027464000067.jpg153161

[0088] The acid generator (B) is a combination of the above-mentioned anion and the above-mentioned organic cation, The acid generator (B) is preferably a compound represented by the formula (Ia-1) to Formula (Ia-3), Formula (Ia-7) ~ Formula (Ia-19), Formula (Ia-22) ~ Formula ( Ia-40) and a cation (b2-1), a cation (b 2-2), a combination with cation (b2-3) or a combination with cation (b2-4).

[0089] The acid generator (B) is preferably a compound represented by formula (B1-1) to formula (B1-60), Among them, those containing an arylsulfonium cation are preferred, Formula (B1-1) ~ Formula (B1-3), Formula (B1-5) ~ Formula (B1-7), Formula (B1-11) ~Formula (B1-14), Formula (B1-20) ~Formula (B1-26), Formula (B1-29), Formula (B Those represented by formulas (1-31) to (B1-60) are particularly preferred. JPEG2026027464000068.jpg191165

[0090] JPEG2026027464000069.jpg249155

[0091] JPEG2026027464000070.jpg239165

[0092] When the acid generator contains a salt (I) and an acid generator (B), the salt (I) and the acid generator (B) The ratio of the salt (I):acid generator (B) to the salt (I) (mass ratio) is usually 1:99 to 99:1. The ratio is preferably 2:98 to 98:2, and more preferably 5:95 to 95:5. More preferably, it is 10:90 to 90:10, and particularly preferably 15:85 to 85 :15.

[0093] <Resist composition> The resist composition of the present invention comprises an acid generator containing a salt (I) and a resin having an acid labile group (hereinafter referred to as Here, the "acid labile group" refers to a group that is detached from the resin (hereinafter referred to as "resin (A)"). When contacted with an acid, the leaving group is eliminated, and the structural unit is converted into a hydrophilic group (e.g., a hydroxyl group). It means a group that converts into a structural unit having a hydroxyl group (a hydroxyl group or a carboxyl group). The resist composition of the present invention generates an acid that is weaker in acidity than the acid generated from the acid generator. It may contain a quencher such as salt (hereinafter referred to as "quencher (C)"). It is preferable that the ink contains a solvent (hereinafter, sometimes referred to as "solvent (E)").

[0094] <Acid generator> In the resist composition of the present invention, the total content of the acid generator is 100% by weight of the resin (A) described below. 00 parts by mass, preferably 1 part by mass or more and 45 parts by mass or less, more preferably 1 part by mass The content is preferably from 3 parts by mass to 40 parts by mass, and more preferably from 3 parts by mass to 40 parts by mass.

[0095] <Resin (A)> The resin (A) contains a structural unit having an acid labile group (hereinafter, sometimes referred to as "structural unit (a1)"). The resin (A) preferably further contains a structural unit other than the structural unit (a1). The structural units other than the structural unit (a1) are preferably structural units having no acid labile group (hereinafter (hereinafter sometimes referred to as "structural unit (s)"), structural unit (a1) and structural unit (s) other than A structural unit (for example, a structural unit having a halogen atom, which will be described later (hereinafter referred to as "structural unit (a4)") a structural unit having a non-leaving hydrocarbon group (hereinafter referred to as "structural unit (a 5)) and other structural units derived from monomers known in the art. Examples include:

[0096] <Structural unit (a1)> The structural unit (a1) is a monomer having an acid labile group (hereinafter referred to as "monomer (a1)"). (in some cases). The acid labile group contained in the resin (A) is 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)) is preferred. JPEG2026027464000071.jpg2298[In formula (1), R a1 , R a2 and R a3 are each independently 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 alicyclic hydrocarbon group having 6 to 18 carbon atoms represents an aromatic hydrocarbon group or a group consisting of these groups, or R a1 and R a2 are combined with each other Together with the carbon atom to which they are bonded, they form an alicyclic hydrocarbon group having 3 to 20 carbon atoms. ma and na each independently represent 0 or 1, and at least one of ma and na represents 1. * denotes a binding site.] TIFF2026027464000072.tif2278[In formula (2), R a1’ and R a2’ are each independently a hydrogen atom or a group having 1 to 1 carbon atoms, represents a hydrocarbon group of 2, and R a3’ represents a hydrocarbon group having 1 to 20 carbon atoms, or R a2’ Reach BiR a3’ are bonded to each other and together with the carbon atoms to which they are bonded and X, form a group having 3 to 20 carbon atoms. A heterocyclic group is formed, and -CH2- contained in the hydrocarbon group and the heterocyclic group is -O- or - May be replaced with S-. X represents an oxygen atom or a sulfur atom. na' represents 0 or 1. * denotes a binding site.]

[0097] R a1 , R a2 and R a3 The alkyl group in the formula (I) is a methyl group, an ethyl group, a propyl group, or a propyl group. Examples of the alkyl group include an alkyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. R a1 , R a2 and R a3 Examples of the alkenyl group in Propenyl, butenyl, isobutenyl, tert-butenyl, pentenyl, Examples include xenyl, heptenyl, octenyl, isooctenyl, and nonenyl groups. . R a1 , R a2 and R a3 The alicyclic hydrocarbon group in Examples of the monocyclic alicyclic hydrocarbon group include a cyclopentyl group, a cyclohexyl group, ... Examples of cycloalkyl groups include cycloheptyl and cyclooctyl groups. Examples of the hydrocarbon group include a decahydronaphthyl group, an adamantyl group, a norbornyl group, and the following groups: (* indicates a bonding site.) a1 , R a2 and R a3 Alicyclic hydrocarbons The group preferably has 3 to 16 carbon atoms. TIFF2026027464000073.tif10159R a1 , R a2 and R a3 The aromatic hydrocarbon group in aryl groups such as an anthryl group, a biphenyl group, and a phenanthryl group; The combined group may be a group in which the above-mentioned alkyl group and alicyclic hydrocarbon group are combined. (e.g., methylcyclohexyl group, dimethylcyclohexyl group, methylnorbornyl group) , cyclohexylmethyl group, adamantylmethyl group, adamantyldimethyl group, norbornyl alkylcycloalkyl groups or cycloalkylalkyl groups such as phenylethyl groups), benzyl Aralkyl groups such as alkyl groups, aromatic hydrocarbon groups (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.), alicyclic hydrocarbon groups Aromatic hydrocarbon groups (p-cyclohexylphenyl group, p-adamantylphenyl group) and the like), and aryl-cycloalkyl groups such as phenylcyclohexyl group. Preferably, ma is 0 and na is 1. R a1 and R a2 -C(R a1 )(R a2 )(R a3 The alicyclic hydrocarbon group preferably has 3 carbon atoms. ~12. * indicates the bonding site with -O-. TIFF2026027464000074.tif35157

[0098] R a1’ , R a2’ and R a3’ The hydrocarbon group in the Examples of the alkyl group include a hydroxyl group, an aromatic hydrocarbon group, and a group formed by combining these groups. can be done. The alkyl group and the alicyclic hydrocarbon group are represented by R a1 , R a2 and R a3 The same groups as those listed in Examples include: Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, Examples include aryl groups such as a phenanthryl group. The combined group may be a group in which the above-mentioned alkyl group and alicyclic hydrocarbon group are combined. (e.g., methylcyclohexyl group, dimethylcyclohexyl group, methylnorbornyl group) , cyclohexylmethyl group, adamantylmethyl group, adamantyldimethyl group, norbornyl alkylcycloalkyl groups or cycloalkylalkyl groups such as phenylethyl groups), benzyl Aralkyl groups such as alkyl groups, aromatic hydrocarbon groups (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.), alicyclic hydrocarbon groups Aromatic hydrocarbon groups (p-cyclohexylphenyl group, p-adamantylphenyl group) and the like), and aryl-cycloalkyl groups such as phenylcyclohexyl group. R a2’ and R a3’ are bonded to each other and together with the carbon atoms to which they are bonded and X, When forming a cyclic group, -C(R a1’ )(R a2’ )-XR a3’ Examples of the groups include the following: * indicates a binding site. TIFF2026027464000075.tif19124R a1’ and R a2’ At least one of these is preferably a hydrogen atom. na' is preferably 0.

[0099] Examples of the group (1) include the following groups. In formula (1), R a1 , R a2 and R a3 is an alkyl group, ma=0, and na= 1. The group is preferably a tert-butoxycarbonyl group. In formula (1), R a1 , R a2 However, together with the carbon atoms to which they are bonded, they form adamannes Forms a methyl group, R a3 is an alkyl group, ma=0, and na=1. In formula (1), R a1 and R a2 are each independently an alkyl group, and R a3 Adama A group in which ma=0 and na=1. Specific examples of the group (1) include the following: * represents a binding site. TIFF2026027464000076.tif113163

[0100] TIFF2026027464000077.tif65156

[0101] Specific examples of group (2) include the following groups: * represents a binding site. TIFF2026027464000078.tif68162

[0102] The monomer (a1) is preferably a monomer having an acid labile group and an ethylenically unsaturated bond. More preferably, it is a (meth)acrylic monomer having an acid labile group.

[0103] Among the (meth)acrylic monomers having an acid labile group, those having 5 to 20 carbon atoms are preferred. Examples of the compound having a bulky structure such as an alicyclic hydrocarbon group include: A resin (A) having a structural unit derived from a monomer (a1) having the above structure is used in a resist composition. This can improve the resolution of the resist pattern.

[0104] As the structural unit derived from a (meth)acrylic monomer having the group (1), preferably , a structural unit represented by formula (a1-0) (hereinafter, may be referred to as structural unit (a1-0) ), a structural unit represented by formula (a1-1) (hereinafter, sometimes referred to as structural unit (a1-1) ) or a structural unit represented by formula (a1-2) (hereinafter, referred to as structural unit (a1-2) More preferably, the structural unit (a1-0) and the structural unit (a1-1) are included. and at least one structural unit selected from the group consisting of structural units (a1-2), More preferably, the structural unit (a1-1) is selected from the group consisting of the structural unit (a1-2). These may be used alone or in combination of two or more. That's fine. TIFF2026027464000079.tif47153 [In formula (a1-0), formula (a1-1) and formula (a1-2), L a01 , L a1 and L a2 are each independently -O- or -O-(CH2) k1 - represents CO-O-, k1 represents an integer of 1 to 7, and * represents the bonding site with -CO-. represent. R a01 , R a4 and R a5 are each independently a hydrogen atom, a halogen atom or a halogen atom It represents an alkyl group having 1 to 6 carbon atoms which may have one or more atoms. R a02 , R a03 and R a04 are each independently an alkyl group having 1 to 8 carbon atoms, 18 alicyclic hydrocarbon groups, aromatic hydrocarbon groups having 6 to 18 carbon atoms, or combinations thereof Represents a group. R a6 and R a7 are each independently an alkyl group having 1 to 8 carbon atoms, an alkyl group having 2 to 8 carbon atoms, alkenyl group, alicyclic hydrocarbon group having 3 to 18 carbon atoms, aromatic hydrocarbon group having 6 to 18 carbon atoms or represents a group formed by combining these. m1 represents an integer of 0 to 14. n1 represents an integer of 0 to 10. n1' represents an integer of 0 to 3.

[0105] R a01 , R a4 and R a5 is preferably a hydrogen atom or a methyl group, more preferably a methyl group. It is a methyl group. L a01 , L a1 and L a2 is preferably an oxygen atom or —O—(CH2) k01 -C OO- (wherein k01 is preferably an integer of 1 to 4, more preferably 1), and more preferably an oxygen atom. R a02 , R a03 , R a04 , R a6 and R a7 Alkyl groups, alkenyl groups, alicyclic groups The hydrocarbon group, aromatic hydrocarbon group, and a group formed by combining these groups include R a1 , R a2 and R a3 Examples of the groups include the same groups as those listed in the above. R a02 , R a03 , and R a04 The alkyl group in the formula (I) is preferably an alkyl group having 1 to 6 carbon atoms. A group, more preferably a methyl group or an ethyl group, and even more preferably a methyl group. do. R a6 and R a7 The alkyl group in the formula (I) is preferably an alkyl group having 1 to 6 carbon atoms. , more preferably a methyl group, an ethyl group, an isopropyl group, or a t-butyl group, Preferred is an ethyl group, an isopropyl group, or a t-butyl group. R a6 and R a7 The alkenyl group in the formula (I) is preferably an alkenyl group having 2 to 6 carbon atoms. and more preferably an ethenyl group, a propenyl group, an isopropenyl group, or a butenyl group. do. R a02 , R a03 , R a04 , R a6 and R a7 The number of carbon atoms in the alicyclic hydrocarbon group is preferably It is 5 to 12, and more preferably 5 to 10. R a02 , R a03 , R a04 , R a6 and R a7 The number of carbon atoms in the aromatic hydrocarbon group is preferably It is 6 to 12, and more preferably 6 to 10. The group in which an alkyl group and an alicyclic hydrocarbon group are combined is The total number of carbon atoms in combination with the group is preferably 18 or less. The group in which an alkyl group and an aromatic hydrocarbon group are combined is The total number of carbon atoms in combination with the group is preferably 18 or less. R a02 and R a03 is preferably an alkyl group having 1 to 6 carbon atoms or an aromatic group having 6 to 12 carbon atoms. It is a hydrocarbon group, more preferably a methyl group, an ethyl group, a phenyl group or a naphthyl group. do. R a04 is preferably an alkyl group having 1 to 6 carbon atoms or an alicyclic hydrocarbon having 5 to 12 carbon atoms. group, more preferably a methyl group, an ethyl group, a cyclohexyl group or an adamantyl group. be. 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, a methyl group or an aromatic hydrocarbon group having 6 to 12 carbon atoms, and more preferably a methyl group or an ethyl group. , isopropyl, t-butyl, ethenyl, phenyl or naphthyl; Among these, an ethyl group, an isopropyl group, a t-butyl group, an ethenyl group, or a phenyl group is particularly preferred. do. m1 is preferably an integer of 0 to 3, and more preferably 0 or 1. n1 is preferably an integer of 0 to 3, and more preferably 0 or 1. n1' is preferably 0 or 1.

[0106] Examples of the structural unit (a1-0) include those represented by the formulae (a1-0-1) to (a1-0-18): and R in the structural unit (a1-0) a01 The equivalent A structure in which the alkyl group is replaced by a hydrogen atom, a halogen atom, a haloalkyl group or another alkyl group. Examples of structural units include formula (a1-0-1) to formula (a1-0-10), formula (a1-0-13) , and a structural unit represented by formula (a1-0-14) are preferred. JPEG2026027464000080.jpg92168

[0107] Examples of the structural unit (a1-1) include those described in JP-A-2010-204646. Among them, structural units derived from the monomers of formula (a1-1-1) to formula (a1 -1-7) and R in the structural unit (a1-1) a4 In accordance with The corresponding methyl group is replaced by a hydrogen atom, a halogen atom, a haloalkyl group, or another alkyl group. A structural unit represented by any one of formulas (a1-1-1) to (a1-1-4) is preferred. The structural unit is more preferred. TIFF2026027464000081.tif39169

[0108] The structural unit (a1-2) is any one of the structural units represented by formula (a1-2-1) to formula (a1-2-14). R in the structural unit (a1-2) and the structural unit (a1-2) a5 The methyl group corresponding to Examples of structural units include those substituted with hydrogen atoms, halogen atoms, haloalkyl groups, or other alkyl groups. Formula (a1-2-2), Formula (a1-2-5), Formula (a1-2-6) and Formula (a1- A structural unit represented by any one of formulas (a1-2-10) to (a1-2-14) is preferred. JPEG2026027464000082.jpg70168

[0109] Resin (A) is a structural unit (a1-0) and / or a structural unit (a1-1) and / or a structural unit (a1-2). When the unit (a1-2) is included, the total content of these units relative to all structural units of the resin (A) is: It is usually 10 to 95 mol %, preferably 15 to 90 mol %, more preferably 20 The content is preferably from 25 to 85 mol %, more preferably from 25 to 70 mol %, and even more preferably from 25 to 70 mol %. It is 30 to 70 mol %.

[0110] The structural unit (a1) having the group (2) is represented by the formula (a1-4). Examples of such structural units include those (hereinafter, may be referred to as "structural unit (a1-4)"). TIFF2026027464000083.tif4666[In formula (a1-4), R a32 is a hydrogen atom, a halogen atom, or a C1 group optionally having a halogen atom Represents an alkyl group of 1 to 6. R a33 is a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, a Alkoxy group, alkoxyalkyl group having 2 to 12 carbon atoms, alkoxy group having 2 to 12 carbon atoms Alkoxy group, alkylcarbonyl group having 2 to 4 carbon atoms, alkylcarbonyl group having 2 to 4 carbon atoms It represents an oxy group, an acryloyloxy group, or a methacryloyloxy group. A a30 is a single bond or * -X a31-(A a32 -X a32 ) nc - represents -R a32 is combined represents the bonding site with the carbon atom. A a32 represents an alkanediyl group having 1 to 6 carbon atoms. X a31 and X a32 each independently represents -O-, -CO-O- or -O-CO-. nc represents 0 or 1. Ia represents an integer of 0 to 4. When Ia is an integer of 2 or more, R in Numbers a33 may be the same or different from each other. R a34 and R a35 each independently represents a hydrogen atom or a hydrocarbon group having 1 to 12 carbon atoms, R a36 represents a hydrocarbon group having 1 to 20 carbon atoms, or R a35 and R a36 are combined with each other and These form a divalent hydrocarbon group having 2 to 20 carbon atoms together with the -CO- to which they are bonded, and the hydrocarbon The -CH2- contained in the alkyl group and the divalent hydrocarbon group is replaced by -O- or -S-. That's fine.]

[0111] R a32 and R a33 Examples of the halogen atom in the formula (I) include a fluorine atom, a chlorine atom, and a bromine atom. Examples include: R a32 Examples 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, phenyl group fluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, propyl group, Perfluorobutyl group, 1,1,2,2,3,3,4,4-octafluorobutyl group, ethyl group, perfluoropentyl group, 2,2,3,3,4,4,5,5,5-nonafluoro Examples include pentyl, pentyl, hexyl and perfluorohexyl groups. R a32 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and is more preferably an ethyl group, and even more preferably a hydrogen atom or a methyl group. R a33 The alkyl group in the formula (I) is a methyl group, an ethyl group, a propyl group, an isopropyl group, or the like. Examples of the butyl group, sec-butyl group, tert-butyl group, pentyl group, and hexyl group are listed below. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, and is preferably a methyl group or an ethyl group. A methyl group is more preferred. R a33 The alkoxy group in the formula (I) is a methoxy group, an ethoxy group, a propoxy group, an isopropyl ... Propoxy group, butoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group The alkoxy group includes an alkoxy group having 1 to 4 carbon atoms. A methoxy group or an ethoxy group is preferred, and a methoxy group is even more preferred. R a33 The alkoxyalkyl group in the formula (I) is a methoxymethyl group or an ethoxyethyl group. , propoxymethyl group, isopropoxymethyl group, butoxymethyl group, sec-butoxy Examples of the alkoxyalkyl group include a methyl group and a tert-butoxymethyl group. An alkoxyalkyl group having 2 to 8 carbon atoms is preferred, and a methoxymethyl group or an ethoxyethyl group is more preferred. A methoxymethyl group is more preferred. R a33 The alkoxyalkoxy group in the formula (I) is a methoxymethoxy group, a methoxyethoxy group, oxy group, ethoxymethoxy group, ethoxyethoxy group, propoxymethoxy group, isopropoxy group butoxymethoxy group, sec-butoxymethoxy group, tert-butoxy The alkoxyalkoxy group is an alkoxyalkoxy group having 2 to 8 carbon atoms. A koxy group is preferred, and a methoxyethoxy group or an ethoxyethoxy group is more preferred. R a33 The alkylcarbonyl group in the formula (I) includes an acetyl group, a propionyl group, and a butyl group. The alkylcarbonyl group is an alkylcarbonyl group having 2 to 3 carbon atoms. is preferred, and an acetyl group is more preferred. R a33 The alkylcarbonyloxy group in the formula (I) is an acetyloxy group, a propionyloxy group, or The alkylcarbonyloxy group includes a hydroxyl group and a butyryloxy group. An alkylcarbonyloxy group having 2 to 3 carbon atoms is preferred, and an acetyloxy group is more preferred. R a33 is a halogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, a An alkoxy group or an alkoxyalkoxy group having 2 to 8 carbon atoms is preferred, and a fluorine atom, an iodide atom, a hydrogen atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group or an ethoxy group A methoxy group is more preferred, and a fluorine atom, an iodine atom, a hydroxy group, a methyl group, More preferred are methoxy and ethoxyethoxy groups.

[0112] *-X a31 -(A a32 -X a32 ) nc - includes *-O-, *-CO-O-, *-OC O-, *-CO-OA a32 -CO-O-, *-O-CO-A a32 -O-, *-OA a32 -CO-O-, *-CO-OA a32 -O-CO-, *-O-CO-A a32 -O-CO-, Among them, *-CO-O- and *-CO-OA are a32 -CO-O- or *- Office Automation a32 -CO-O- is preferred.

[0113] A a32 The alkanediyl group in the formula (I) includes a methylene group, an ethylene group, a 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-methyl Propane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1, 4-diyl group and 2-methylbutane-1,4-diyl group. A a32 is preferably a methylene group or an ethylene group.

[0114] A a30 is a single bond, *-CO-O- or *-CO-OA a32 -CO-O- Preferably, it is a single bond, *-CO-O-, or *-CO-O-CH2-CO-O-. A single bond or *-CO-O- is more preferred, and a single bond or *-CO-O- is even more preferred.

[0115] la is preferably 0, 1 or 2, more preferably 0 or 1, and even more preferably 0. R a34 , R a35 and R a36 The hydrocarbon group in the formula (I) may be an alkyl group or an alicyclic hydrocarbon group. , aromatic hydrocarbon groups, and groups combining these groups. The alkyl group includes a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and a methyl group. Examples include a sil group, a heptyl group, and an octyl group. The alicyclic hydrocarbon group may be either monocyclic or polycyclic. Examples of the cyclopentyl group include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group. Examples of the polycyclic alicyclic hydrocarbon group include decahydronaphthalene, butyl group, adamantyl group, norbornyl group, and the following groups (* indicates a bonding site): Examples include: TIFF2026027464000084.tif10151Aromatic hydrocarbon groups include phenyl, naphthyl, anthryl, biphenyl, Examples include aryl groups such as a phenanthryl group. The combined group may be a group in which the above-mentioned alkyl group and alicyclic hydrocarbon group are combined. (e.g., methylcyclohexyl group, dimethylcyclohexyl group, methylnorbornyl group) , cyclohexylmethyl group, adamantylmethyl group, adamantyldimethyl group, norbornyl alkylcycloalkyl groups or cycloalkylalkyl groups such as phenylethyl groups), benzyl Aralkyl groups such as alkyl groups, aromatic hydrocarbon groups (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.), alicyclic hydrocarbon groups Aromatic hydrocarbon groups (p-cyclohexylphenyl group, p-adamantylphenyl group) and aryl-cycloalkyl groups such as phenylcyclohexyl groups. , R a36 Examples of the alkyl group include an alkyl group having 1 to 18 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, Aromatic hydrocarbon groups having 6 to 18 carbon atoms or groups formed by combining these Examples include:

[0116] R a34 is preferably a hydrogen atom. R a35 is preferably a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or a It is an alicyclic hydrocarbon group, more preferably a methyl group or an ethyl group. R a36 The hydrocarbon group is preferably an alkyl group having 1 to 18 carbon atoms, a Alicyclic hydrocarbon groups, aromatic hydrocarbon groups having 6 to 18 carbon atoms, or combinations thereof More preferably, it is a group formed by an alkyl group having 1 to 18 carbon atoms, a group formed by an alkyl group having 3 to 1 carbon atoms, R is an alicyclic hydrocarbon group having 8 carbon atoms or an aralkyl group having 7 to 18 carbon atoms. a36 Archi in The R alkyl group and the alicyclic hydrocarbon group are preferably unsubstituted. a36 Aromatic carbonization in The hydrogen group is preferably an aromatic ring having an aryloxy group having 6 to 10 carbon atoms.

[0117] -OC(R a34 )(R a35 )-OR a36 is an acid (e.g. p-toluenesulfonic acid), it is eliminated to form a hydroxy group. -OC(R a34 )(R a35 )-OR a36 is attached to the o- or p-position of the benzene ring It is preferable that the bond is at the p-position, and it is more preferable that the bond is at the p-position.

[0118] Examples of the structural unit (a1-4) include those described in JP-A-2010-204646. The structural units derived from the monomers of formula (a1-4-1) to formula (a1-4-2) are preferred. -4-24) and R in the structural unit (a1-4) a32 to A structure in which the corresponding hydrogen atom is replaced by a halogen atom, a haloalkyl group, or an alkyl group. More preferably, the units are those of the formula (a1-4-1) to the formula (a1-4-5), -4-10), formula (a1-4-13), formula (a1-4-14), formula (a1-4-19), Examples of structural units are those represented by formula (a1-4-20). JPEG2026027464000085.jpg132168

[0119] When the resin (A) contains the structural unit (a1-4), the content thereof is determined based on the total structure of the resin (A). It is preferably 10 to 95 mol %, more preferably 15 to 90 mol %, based on the total of the units. It is more preferable that the content is 20 to 85 mol %, and even more preferable that the content is 20 to 70 mol %. It is even more preferable that the content is 20 to 60 mol %, and it is particularly preferable that the content is 20 to 60 mol %.

[0120] The structural unit derived from a (meth)acrylic monomer having the group (2) includes a structural unit represented by the formula (a1 -5) (hereinafter sometimes referred to as "structural unit (a1-5)") can be. TIFF2026027464000086.tif4253 formula (a1-5), R a8 is an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, a hydrogen atom or a halogen atom. represents a halogen atom. Z a1 is a single bond or -(CH2) h3 -CO-L 54 -, h3 is 1 to 4 represents an integer, and * represents L 51 represents the binding site with L 51 , L 52 , L 53 and L 54 each independently represents -O- or -S-. s1 represents an integer of 1 to 3. s1' represents an integer of 0 to 3.

[0121] Examples of halogen atoms include fluorine atoms and chlorine atoms, with fluorine atoms being preferred. Examples of the alkyl group having 1 to 6 carbon atoms which may have a halogen atom include a methyl group, an ethyl group, and a methyl group. propyl, butyl, pentyl, hexyl, heptyl, octyl, fluoro Examples include a trifluoromethyl group and a trifluoromethyl group. In formula (a1-5), R a8 is a hydrogen atom, a methyl group, or a trifluoromethyl group preferable. L 51 is preferably an oxygen atom. L 52 and L 53 Among these, it is preferred that one is —O— and the other is —S—. s1 is preferably 1. s1' is preferably an integer of 0 to 2. Z a1 is preferably a single bond or —CH2—CO—O—.

[0122] Examples of the structural unit (a1-5) include those described in JP-A-2010-61117. Among them, structural units derived from the monomers of formula (a1-5-1) to formula (a1-5- 4), and the structural units represented by formula (a1-5-1) or formula (a1-5-2) are preferred. ) is more preferred. TIFF2026027464000087.tif31130

[0123] When the resin (A) contains the structural unit (a1-5), the content thereof is determined based on the total structure of the resin (A). The content is preferably 1 to 50 mol %, more preferably 3 to 45 mol %, and more preferably 5 to 40 mol %, based on the unit. % by mole is more preferable, and 5 to 30 mol % is even more preferable.

[0124] Further, examples of the structural unit (a1) include the following structural units. TIFF2026027464000088.tif27161

[0125] When the resin (A) contains structural units such as those of (a1-3-1) to (a1-3-7) The content thereof is preferably 10 to 95 mol % based on the total structural units of the resin (A), and more preferably 15 to 95 mol %. More preferably, the content is 20 to 90 mol %, even more preferably, 20 to 85 mol %, and 20 to 70 mol %. It is even more preferable, and 20 to 60 mol % is particularly preferable.

[0126] <Structural unit(s)> The structural unit (s) is a monomer that does not have an acid labile group (hereinafter referred to as "monomer (s)"). The monomer from which the structural unit (s) is derived is an acid-inhibiting monomer known in the resist field. Monomers without stabilizing groups can be used. The structural unit (s) preferably has a hydroxy group or a lactone ring. A structural unit having an oxy group and not having an acid labile group (hereinafter referred to as "structural unit (a2)") and / or a structural unit having a lactone ring and no acid labile group (hereinafter referred to as "structural unit"). When a resin containing the structural unit (a3) ​​is used in the resist composition of the present invention, This can improve the resolution of the resist pattern and the adhesion to the substrate.

[0127] <Structural unit (a2)> The hydroxy group of the structural unit (a2) may be an alcoholic hydroxy group or a phenolic hydroxy group. It may also be a hydroxyl group. When a resist pattern is produced from the resist composition of the present invention, KrF is used as the exposure light source. High energy rays such as excimer laser (248 nm), electron beam, or EUV (extreme ultraviolet) are used. In this case, the structural unit (a2) may be a structural unit having a phenolic hydroxy group ( a2) is preferred, and it is more preferred to use the structural unit (a2-A) described below. When an ArF excimer laser (193 nm) or the like is used, the structural unit (a2) is The structural unit (a2) having an alcoholic hydroxy group is preferred, and the structural unit (a2) described below is It is more preferable to use the structural unit (a2) alone. It may contain two or more kinds.

[0128] The structural unit (a2) having a phenolic hydroxy group is a structural unit of the formula (a 2-A) (hereinafter sometimes referred to as "structural unit (a2-A)") can be done. TIFF2026027464000089.tif4753[In formula (a2-A), R a50 is a hydrogen atom, a halogen atom, or a group having 1 to 6 carbon atoms which may have a halogen atom represents an alkyl group represented by the formula: R a51 is a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, a Alkoxy group, alkoxyalkyl group having 2 to 12 carbon atoms, alkoxy group having 2 to 12 carbon atoms Alkoxy group, alkylcarbonyl group having 2 to 4 carbon atoms, alkylcarbonyl group having 2 to 4 carbon atoms It represents an oxy group, an acryloyloxy group, or a methacryloyloxy group. A a50 is a single bond or *-X a51 -(A a52 -X a52 ) nb - represents -R a50 is combined represents the bonding site with the carbon atom. Aa52 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 an integer of 0 to 4. When mb is an integer of 2 or more, multiple R in Numbers a51 may be the same or different from each other.

[0129] R a50 and R a51 Examples of the halogen atom in the formula (I) include a fluorine atom, a chlorine atom, and a bromine atom. Examples include: R a50 Examples 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, phenyl group fluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, propyl group, Perfluorobutyl group, 1,1,2,2,3,3,4,4-octafluorobutyl group, ethyl group, perfluoropentyl group, 2,2,3,3,4,4,5,5,5-nonafluoro Examples include pentyl, pentyl, hexyl and perfluorohexyl groups. R a50 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and is more preferably an ethyl group, and even more preferably a hydrogen atom or a methyl group. R a51 The alkyl group in the formula (I) is a methyl group, an ethyl group, a propyl group, an isopropyl group, or the like. Examples of the butyl group, sec-butyl group, tert-butyl group, pentyl group, and hexyl group are listed below. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, and is preferably a methyl group or an ethyl group. A methyl group is more preferred. R a51 The alkoxy group in the formula (I) is a methoxy group, an ethoxy group, a propoxy group, an isopropyl ... Examples include a propoxy group, a butoxy group, a sec-butoxy group, and a tert-butoxy group. The alkoxy group is preferably an alkoxy group having 1 to 4 carbon atoms, and is preferably a methoxy group or an ethoxy group. More preferred is a methoxy group. R a51 The alkoxyalkyl group in the formula (I) is a methoxymethyl group or an ethoxyethyl group. , propoxymethyl group, isopropoxymethyl group, butoxymethyl group, sec-butoxy Examples of the alkoxyalkyl group include a methyl group and a tert-butoxymethyl group. An alkoxyalkyl group having 2 to 8 carbon atoms is preferred, and a methoxymethyl group or an ethoxyethyl group is more preferred. A methoxymethyl group is more preferred. R a51 The alkoxyalkoxy group in the formula (I) is a methoxymethoxy group, a methoxyethoxy group, oxy group, ethoxymethoxy group, ethoxyethoxy group, propoxymethoxy group, isopropoxy group butoxymethoxy group, sec-butoxymethoxy group, tert-butoxy The alkoxyalkoxy group is an alkoxyalkoxy group having 2 to 8 carbon atoms. A koxy group is preferred, and a methoxyethoxy group or an ethoxyethoxy group is more preferred. R a51 The alkylcarbonyl group in the formula (I) includes an acetyl group, a propionyl group, and a butyl group. The alkylcarbonyl group is an alkylcarbonyl group having 2 to 3 carbon atoms. is preferred, and an acetyl group is more preferred. R a51The alkylcarbonyloxy group in the formula (I) is an acetyloxy group, a propionyloxy group, or The alkylcarbonyloxy group includes a hydroxyl group and a butyryloxy group. An alkylcarbonyloxy group having 2 to 3 carbon atoms is preferred, and an acetyloxy group is more preferred. R a51 is a halogen atom, a hydroxy group, an alkyl group having 1 to 4 carbon atoms, a An alkoxy group or an alkoxyalkoxy group having 2 to 8 carbon atoms is preferred, and a fluorine atom, an iodide atom, a hydrogen atom, a hydroxy group, a methyl group, a methoxy group, an ethoxy group, an ethoxyethoxy group or an ethoxy group A methoxy group is more preferred, and a fluorine atom, an iodine atom, a hydroxy group, a methyl group, More preferred are methoxy and ethoxyethoxy groups.

[0130] *-X a51 -(A a52 -X a52 ) nb - includes *-O-, *-CO-O-, *-OC O-, *-CO-OA a52 -CO-O-, *-O-CO-A a52 -O-, *-OA a52 -CO-O-, *-CO-OA a52 -O-CO-, *-O-CO-A a52 -O-CO-, Among them, *-CO-O- and *-CO-OA are a52 -CO-O- or *- Office Automation a52 -CO-O- is preferred.

[0131] A a52 The alkanediyl group in the formula (I) includes a methylene group, an ethylene group, a 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-methyl Propane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1, 4-diyl group and 2-methylbutane-1,4-diyl group. A a52 is preferably a methylene group or an ethylene group.

[0132] A a50 is a single bond, *-CO-O- or *-CO-OA a52 -CO-O- Preferably, it is a single bond, *-CO-O-, or *-CO-O-CH2-CO-O-. A single bond or *-CO-O- is more preferred, and a single bond or *-CO-O- is even more preferred.

[0133] mb is preferably 0, 1 or 2, more preferably 0 or 1, and even more preferably 0. At least one hydroxy group may be bonded to the meta or para position of the benzene ring. Preferably, the phenyl group is bonded to the meta position, and more preferably to the hydroxyl group. When the compound has the formula (I), the two hydroxy groups are preferably bonded to the meta and para positions, respectively. I wish.

[0134] Examples of the structural unit (a2-A) include those described in JP-A-2010-204634 and JP-A-2012- Examples of structural units include those derived from monomers described in Japanese Patent Publication No. 12577. The structural unit (a2-A) is represented by formula (a2-2-1) to formula (a2-2-24). In the structural units represented by formulas (a2-2-1) to (a2-2-24), , R in structural unit (a2-A) a50 The corresponding methyl group is a hydrogen atom, a halogen atom , haloalkyl groups or other alkyl groups. a2-A) is a structural unit represented by formula (a2-2-1) to formula (a2-2-4), -2-6), structural units represented by formula (a2-2-8), structural units represented by formula (a2-2 -12) to (a2-2-18) and structural units represented by formulas (a2-2-1) to (a2 -2-4), structural units represented by formula (a2-2-6), structural units represented by formula (a2-2 -8), structural units represented by formulas (a2-2-12) to (a2-2-18), In the structural unit, R in the structural unit (a2-A) a50 The methyl group corresponding to The structural unit represented by formula (a2-2-3) is preferably a structural unit represented by formula (a2-2-3) , a structural unit represented by formula (a2-2-4), a structural unit represented by formula (a2-2-8), a structural unit represented by formula (a2-2-9), Structural units represented by formulas (a2-2-12) to (a2-2-14), formula (a2-2-18) and a structural unit represented by formula (a2-2-3), a structural unit represented by formula (a2-2-4), Structural units represented by formula (a2-2-8), structural units represented by formula (a2-2-12) to formula (a2-2-13), In the structural unit represented by formula (a2-2-14), the structural unit represented by formula (a2-2-18) In the structural unit (a2-A), R a50 The methyl group corresponding to The structural unit represented by formula (a2-2-3) and the structural unit represented by formula (a2-2-4) are more preferred. a2-2-4), a structural unit represented by formula (a2-2-8) and a structural unit represented by formula (a 2-2-3), a structural unit represented by formula (a2-2-4), a structural unit represented by formula (a2- 2-8), R in the structural unit (a2-A) a50 Equivalent to It is more preferable that the structural unit is a structural unit in which a methyl group is substituted for a hydrogen atom. JPEG2026027464000090.jpg78165

[0135] Content of structural unit (a2-A) when structural unit (a2-A) is contained in resin (A) is preferably 5 to 80 mol %, more preferably 10 to 70 mol %, based on all structural units. % by mole, more preferably 15 to 65 mol %, and even more preferably 20 to 65 mol %. It is 65 mol%. The structural unit (a2-A) can be prepared by, for example, polymerizing the structural unit (a1-4) and then reacting the polymer with p-toluenesulfonyl ether. It can be incorporated into the resin (A) by treating it with an acid such as enesulfonic acid. After polymerization using acetoxystyrene, etc., tetramethylammonium hydroxide, etc. By treating with an alkali, the structural unit (a2-A) can be incorporated into the resin (A). can.

[0136] The structural unit (a2) having an alcoholic hydroxy group includes a structural unit represented by the formula ( a2-1) (hereinafter referred to as "structural unit (a2-1)") Examples include: TIFF2026027464000091.tif4461 formula (a2-1), L a3 is -O- or *-O-(CH2) k2 represents -CO-O-, k2 represents an integer of 1 to 7. * represents the bonding site with —CO—. R a14 represents a hydrogen atom or a methyl group. R a15 and R a16 each independently represents a hydrogen atom, a methyl group, or a hydroxy group. o1 represents an integer between 0 and 10.

[0137] In equation (a2-1), L a3 is preferably -O-, -O-(CH2) f1 -CO-O- (wherein f1 represents an integer of 1 to 4), and 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 0 to 3, and more preferably 0 or 1.

[0138] Examples of the structural unit (a2-1) include those described in JP-A-2010-204646. The structural units derived from the monomers of formula (a2-1-1) to formula (a2-1-6) are examples. ) is preferred, and a structural unit represented by any one of the formulas (a2-1-1) to (a2-1-4) The structural unit represented by formula (a2-1-1) or formula (a2-1- The structural unit represented by 3) is more preferred. TIFF2026027464000092.tif54150

[0139] When the resin (A) contains the structural unit (a2-1), its content is determined based on the total amount of all structural units in the resin (A). It is usually 1 to 45 mol %, preferably 1 to 40 mol %, more preferably It is preferably 1 to 35 mol %, more preferably 1 to 20 mol %, and even more preferably The content is usually 1 to 10 mol %.

[0140] <Structural unit (a3)> The lactone ring contained in the structural unit (a3) ​​is a β-propiolactone ring, a γ-butyrolactone ring, or It may be a monocyclic ring such as a lactone ring or a δ-valerolactone ring, or a condensed ring of a monocyclic lactone ring with another ring. Preferably, the ring is a γ-butyrolactone ring, an adamantane lactone ring, or a γ -Bridged ring containing a butyrolactone ring structure (for example, a structural unit represented by the following formula (a3-2)) Examples include:

[0141] The structural unit (a3) ​​is preferably a structural unit represented by the formula (a3-1), the formula (a3-2), the formula (a3-3), or a structural unit represented by formula (a3-4). One of these may be contained alone, Two or more types may be contained. TIFF2026027464000093.tif52167 [In formula (a3-1), formula (a3-2), formula (a3-3) and formula (a3-4), L a4 , L a5 and L a6 are each independently -O- or -O-(CH2) k3 - It represents a group represented by CO—O— (k3 represents an integer of 1 to 7). L a7 -O-, *-OL a8 -O-, *-OL a8 -CO-O-, *-OL a8 -CO-OL a9 -CO-O- or *-OL a8 -O-CO-L a9 -O- vinegar. L a8 and L a9 each independently represents an alkanediyl group having 1 to 6 carbon atoms. * indicates the bonding site with the carbonyl group. R a18 , R a19 and R a20 each independently represents a hydrogen atom or a methyl group. R a24 is a hydrogen atom, a halogen atom, or a group having 1 to 10 carbon atoms which may have a halogen atom 6 represents an alkyl group. 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 are each independently a carboxy group, a cyano group or a carbon atom. It represents an aliphatic hydrocarbon group having 1 to 4 prime numbers. p1 represents an integer of 0 to 5. q1 represents an integer of 0 to 3. r1 represents an integer of 0 to 3. w1 represents an integer of 0 to 8. When p1, q1, r1 and / or w1 are 2 or more, multiple R a21 , R a22 , R a2 3 and / or R a25 may be the same as or different from each other.

[0142] R a21 , R a22 , R a23 and R a25 The aliphatic hydrocarbon group in group, propyl group, isopropyl group, butyl group, sec-butyl group and tert-butyl group Examples of alkyl groups include: R a24 The halogen atoms in the formula (I) include fluorine, chlorine, bromine and iodine atoms. Examples include atoms. R a24 The alkyl group in the formula (I) is a methyl group, an ethyl group, a propyl group, an isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, and hexyl group, etc. Preferably, the alkyl group has 1 to 4 carbon atoms, and more preferably, the methyl group. or an ethyl group. R a24 Examples of the alkyl group having a halogen atom in the formula (I) include a trifluoromethyl group, Perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluoro perfluorobutyl group, perfluorosec-butyl group, perfluorotert-butyl group, perfluoropentyl group, perfluorohexyl group, trichloromethyl group, tribromomethyl group Examples include a methyl group and a triiodomethyl group. L a8 and L a9 The alkanediyl group in the formula (I) is a methylene group, an ethylene group, a propane group, or a methyl group. Pan-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pe hexane-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, pentaerythritol Examples include 2-methylbutane-1,4-diyl group and 2-methylbutane-1,4-diyl group.

[0143] In formulas (a3-1) to (a3-3), L a4 ~L a6 are each independently preferred or -O- or *-O-(CH2) k3 In -CO-O-, k3 is any of 1 to 4 groups each of which is an integer, more preferably -O- and *-O-CH2-CO-O-, and An oxygen atom is preferred. 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. It is a methyl group. p1, q1, and r1 each independently represent an integer of preferably 0 to 2, More preferably, it is 0 or 1.

[0144] In formula (a3-4), R a24 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. is preferably a hydrogen atom, a methyl group, or an ethyl group, and more preferably a It is 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 *-OL a8 -CO-O-, more preferably -O-, -O-CH2-CO-O- or -O-C2H4-CO-O-. w1 is preferably an integer of 0 to 2, and more preferably 0 or 1. In particular, the formula (a3-4) is preferably the formula (a3-4)'. TIFF2026027464000094.tif4051(in the formula, R a24 , L a7 has the same meaning as above.)

[0145] The structural unit (a3) ​​may be a monomer described in JP-A-2010-204646. , the monomers described in JP-A-2000-122294, and JP-A-2012-41274 Examples of the structural unit (a3) ​​include structural units derived from the monomers described in the above publication. , 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 (a3-4-1 2), and in the structural unit, the structural unit represented by formula (a3-1) to formula (a3-2) R in a3-4) a18 , R a19 , R a20 and R a24 The methyl group corresponding to Atom-substituted structural units are preferred.

[0146] JPEG2026027464000095.jpg117167

[0147] When the resin (A) contains the structural unit (a3), the total content of the structural unit (a3) ​​is the total content of all structural units of the resin (A). It is usually 5 to 70 mol %, preferably 10 to 65 mol %, more preferably The content is preferably 10 to 60 mol %. In addition, the structural unit (a3-1), the structural unit (a3-2), the structural unit (a3-3) or the structural unit (a3-4) The content of the units (a3-4) is 5 to 60 moles per total structural units of the resin (A). % by mole, more preferably 5 to 50 mol %, and even more preferably 10 to 50 mol %.

[0148] <Structural unit (a4)> Examples of the structural unit (a4) include the following structural units. TIFF2026027464000096.tif3066[In formula (a4), R 41 represents a hydrogen atom or a methyl group. R 42 represents a saturated hydrocarbon group having 1 to 24 carbon atoms and containing a fluorine atom, The —CH2— contained in the group may be replaced with —O— or —CO—. R 42 The saturated hydrocarbon group represented by the formula (I) is a chain hydrocarbon group and a monocyclic or polycyclic alicyclic hydrocarbon group. groups, and groups formed by combining these groups.

[0149] Examples of the chain hydrocarbon group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, Hexyl group, heptyl group, octyl group, decyl group, dodecyl group, pentadecyl group, hexa Examples include decyl, heptadecyl, and octadecyl groups. The hydrogen group includes a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and cycloalkyl groups such as methyl group; decahydronaphthyl group, adamantyl group, norbornyl group and polycyclic and alicyclic hydrocarbon groups such as the following groups (* indicates a bonding site): TIFF2026027464000097.tif11159The group formed by the combination may be one or more alkyl groups or one or more alkanedi groups. and groups formed by combining an alkyl group with one or more alicyclic hydrocarbon groups. -alkanediyl group-alicyclic hydrocarbon group, -alicyclic hydrocarbon group-alkyl group, -alkanediyl group-alicyclic hydrocarbon group Examples include a candiyl group-alicyclic hydrocarbon group-alkyl group.

[0150] The structural unit (a4) includes the formula (a4-0), the formula (a4-1), the formula (a4-2), the formula (a4-3), the formula (a4-4), the formula (a4-5), the formula (a4-6), the formula (a4-7), the formula (a4-8), the formula (a4-9), the formula (a4-10), the formula (a4-11), the formula (a4-12), the formula (a4-13), the formula ( a4-3) and a structure represented by at least one selected from the group consisting of formula (a4-4) Units include: TIFF2026027464000098.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 is a perfluoroalkanediyl group having 1 to 8 carbon atoms or a perfluoroalkanediyl group having 3 to 12 carbon atoms. represents a fluorocycloalkanediyl group. R 6 represents a hydrogen atom or a fluorine atom.

[0151] L 4a The divalent saturated aliphatic hydrocarbon group in linear alkanediyl groups such as pan-1,3-diyl and butane-1,4-diyl groups, ethoxylated propane-1,1-diyl group, propane-1,2-diyl group, butane-1,3-diyl group, 2- Branched groups such as methylpropane-1,3-diyl and 2-methylpropane-1,2-diyl groups alkanediyl groups. L 3a The perfluoroalkanediyl group in Fluoroethylene 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, and the like. L 3a The perfluorocycloalkanediyl group in perfluorocyclopentanediyl group, perfluorocycloheptanediyl group yl group, perfluoroadamantanediyl group, and the like.

[0152] L 4a is preferably a single bond, a methylene group or an ethylene group, more preferably a single bond, bond, a methylene group. L 3a is preferably a perfluoroalkanediyl group having 1 to 6 carbon atoms, more preferably or a perfluoroalkanediyl group having 1 to 3 carbon atoms.

[0153] The structural unit (a4-0) may be the following structural unit or a structural unit ( a4-0) in R 5 The structural unit in which the methyl group corresponding to can be. JPEG2026027464000099.jpg95165

[0154] Examples of the structural unit (a4) include a structural unit represented by formula (a4-1). TIFF2026027464000100.tif4670[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, The -CH2- contained in the hydrocarbon group may be replaced with -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 the formula (ag 1), where A a41 and R a42 At least one of the The group has a halogen atom (preferably a fluorine atom). TIFF2026027464000101.tif1384 [In formula (a-g1), s represents 0 or 1. A a42 and A a44 are each independently a divalent group having 1 to 5 carbon atoms which may have a substituent. Represents a saturated hydrocarbon group. A a43 is a single bond or a divalent aliphatic hydrocarbon having 1 to 5 carbon atoms which may have a substituent. Represents a group. X a41 and X a42are each independently -O-, -CO-, -CO-O- or -O-CO - represents. However, A a42 , A a43 , A a44 , X a41 and X a42 The total number of carbon atoms is 7 or less. * indicates the binding site, and the * on the right is -O-CO-R a42 ]

[0155] R a42 The saturated hydrocarbon group in the formula (I) is a chain saturated hydrocarbon group or a monocyclic or polycyclic alicyclic group. saturated hydrocarbon groups of the formula: do. Examples of the chain saturated hydrocarbon group include a methyl group, an ethyl group, a propyl group, a butyl group, and a pentyl group. group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, pentadecyl group, heptyl group, Examples include a decyl group, a heptadecyl group, and an octadecyl group. Examples of the monocyclic or polycyclic alicyclic saturated hydrocarbon group include a cyclopentyl group and a cyclohexyl group. cycloalkyl groups such as cycloheptyl and cyclooctyl groups; decahydronaphthyl groups; Polycyclic aliphatic groups such as adamantyl group, norbornyl group, and the following groups (* indicates a bonding site): Examples include cyclic saturated hydrocarbon groups. TIFF2026027464000102.tif11159The group formed by the combination may be one or more alkyl groups or one or more alkanedi groups. and groups formed by combining an alkyl group with one or more alicyclic saturated hydrocarbon groups. -alkanediyl group-alicyclic saturated hydrocarbon group, -alicyclic saturated hydrocarbon group-alkanediyl group Examples include an -alkanediyl group, -alicyclic saturated hydrocarbon group, and -alkyl group.

[0156] R a42The substituents that may be possessed by the group (a-g3) include a halogen atom and a group represented by the formula (a-g3): The halogen atom may be at least one selected from the group consisting of fluorine, ... Examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferred. . TIFF2026027464000103.tif965[In 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 R a42 represents the binding site with However, R a42 -X a43 -A a45 In R a42 If A does not have a halogen atom, a4 5 represents an aliphatic hydrocarbon group having 1 to 17 carbon atoms and at least one halogen atom .

[0157] A a45 The aliphatic hydrocarbon group in group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, penta Alkyl groups such as decyl, hexadecyl, heptadecyl, and octadecyl groups; Monocyclic groups such as cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups alicyclic hydrocarbon groups; and decahydronaphthyl groups, adamantyl groups, norbornyl groups, and and polycyclic and alicyclic hydrocarbon groups such as the following groups (* represents a bonding site): TIFF2026027464000104.tif11159The group formed by the combination may be one or more alkyl groups or one or more alkanedi groups. and groups formed by combining an alkyl group with one or more alicyclic hydrocarbon groups. -alkanediyl group-alicyclic hydrocarbon group, -alicyclic hydrocarbon group-alkyl group, -alkanediyl group-alicyclic hydrocarbon group Examples include a candiyl group-alicyclic hydrocarbon group-alkyl group.

[0158] R a42 is preferably an aliphatic hydrocarbon group which may have a halogen atom, an alkyl group having a group and / or an aliphatic hydrocarbon group having a group represented by formula (a-g3): is more preferred. R a42 When is an aliphatic hydrocarbon group having a halogen atom, it is preferable that It is preferably an aliphatic hydrocarbon group having a perfluoroalkyl group or a perfluoroalkyl group. and preferably a perfluoroalkyl group having 1 to 6 carbon atoms. and particularly preferably a perfluoroalkyl group having 1 to 3 carbon atoms. Examples of alkyl groups include perfluoromethyl groups, perfluoroethyl groups, and perfluoropropyl groups. perfluorobutyl group, perfluoropentyl group, perfluorohexyl group, Examples include a fluoroheptyl group and a perfluorooctyl group. Examples of the alkyl group include a perfluorocyclohexyl group. R a42 is an aliphatic hydrocarbon group having a group represented by formula (a-g3), -g3) and the number of carbon atoms contained in the group represented by R a42 The total number of carbon atoms is preferably 15 or less. When the group represented by formula (a-g3) is contained as a substituent, , the number is preferably one.

[0159] R a42is an aliphatic hydrocarbon group having a group represented by formula (a-g3), R a42 teeth, More preferred is a group represented by formula (a-g2). TIFF2026027464000105.tif879[In formula (a-g2), A a46 represents a divalent aliphatic hydrocarbon group having 1 to 17 carbon atoms which may have a halogen atom. Represents. X a44 represents **-O-CO- or **-CO-O- (** represents A a46 The binding site represent). 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 in A is 18 or less. a46 and A a47 of At least one of them has at least one halogen atom. * indicates the bonding site with the carbonyl group.]

[0160] A a46 The aliphatic hydrocarbon group preferably has 1 to 6 carbon atoms, and more preferably 1 to 3 carbon atoms. A a47 The aliphatic hydrocarbon group preferably has 4 to 15 carbon atoms, more preferably 5 to 12 carbon atoms, A a47 is more preferably a cyclohexyl group or an adamantyl group.

[0161] A preferred structure of the group represented by formula (a-g2) is the following structure (* indicates a carbonyl group): (This is the binding site for ATP). JPEG2026027464000106.jpg13161

[0162] A a41The alkanediyl group in the formula (I) includes a methylene group, an ethylene group, a propane-1, 3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1 linear alkanediyl groups such as propane-1,2-diyl, butane-1,6-diyl; ,3-diyl group, 2-methylpropane-1,2-diyl group, 1-methylbutane-1,4- and branched alkanediyl groups such as 2-methylbutane-1,4-diyl and 2-methylbutane-1,4-diyl. do. A a41 The substituents in the alkanediyl group include a hydroxy group and an alkanediyl group having 1 to 6 carbon atoms. Examples thereof include an alkoxy group. A a41 is preferably an alkanediyl group having 1 to 4 carbon atoms, more preferably It is preferably an alkanediyl group having 2 to 4 carbon atoms, and more preferably an ethylene group.

[0163] A in the group represented by formula (a-g1) a42 , A a43 and A a44 The bivalent saturated The hydrocarbon group may be a straight-chain or branched alkanediyl group or a monocyclic or polycyclic divalent alicyclic group. By combining a cycloaliphatic hydrocarbon group with an alkanediyl group and a divalent alicyclic hydrocarbon group, Specifically, a methylene group, an ethylene group, a propane-1 ,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, 1-methyl Propane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane Examples include a pan-1,2-diyl group. A a42 , A a43 and A a44 The substituent of the divalent saturated hydrocarbon group represented by is hydroxyl. Examples of the alkoxy group include an alkoxy group and an alkoxy group having 1 to 6 carbon atoms. Preferably, s is 0.

[0164] In the group represented by formula (a-g1), X a42 is -O-, -CO-, -CO-O- or Examples of the -O-CO- group include the following groups: ** indicates the binding site, and ** indicates -O-CO-R a42 This is the binding site for TIFF2026027464000107.tif54162

[0165] The structural unit represented by formula (a4-1) includes the following structural units and R in the structural unit represented by formula (a4-1) a41 A methyl group corresponding to Examples of structural units that have been replaced include: JPEG2026027464000108.jpg167144

[0166] TIFF2026027464000109.tif66133

[0167] The structural unit (a4) also includes a structural unit represented by formula (a4-2). TIFF2026027464000110.tif4365[In formula (a4-2), R f5 represents a hydrogen atom or a methyl group. L 44 represents an alkanediyl group having 1 to 6 carbon atoms, and —C H2- may be replaced by -O- or -CO-. R f6 represents a saturated hydrocarbon group having 1 to 20 carbon atoms and containing a fluorine atom. However, L 44 and R f6 The maximum total carbon number is 21.]

[0168] L 44The alkanediyl group having 1 to 6 carbon atoms is A a41 For example, the alkanediyl group Examples of the groups include the same groups as those mentioned above. R f6 The saturated hydrocarbon group of R a42 Examples of the groups include the same groups as those exemplified in L 44 The alkanediyl group having 1 to 6 carbon atoms is an alkanediyl group having 2 to 4 carbon atoms. An aryl group is preferred, and an ethylene group is more preferred.

[0169] Examples of the structural unit represented by formula (a4-2) include those represented by formula (a4-1-1) to formula (a4 -1-11) are structural units represented by the structural unit (a4-2). R f5 The structural unit in which the corresponding methyl group is replaced by a hydrogen atom is also represented by formula (a4-2). It is one of the structural units.

[0170] The structural unit (a4) also includes a structural unit represented by formula (a4-3). TIFF2026027464000111.tif5771[In 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. vinegar. X f12 represents *-O-CO- or *-CO-O- (* represents A f13 represents the binding site with ). A f14 represents a saturated hydrocarbon group having 1 to 17 carbon atoms which may contain a fluorine atom. However, A f13 and A f14 At least one of L has a fluorine atom, 5 , Af13 and A f14 The total number of carbon atoms in a molecule is limited to 20.

[0171] L 5 The alkanediyl group in a41 As exemplified by the alkanediyl group in The same groups as those mentioned above can be mentioned. A f13 The divalent saturated hydrocarbon group optionally having a fluorine atom in or a divalent chain saturated hydrocarbon group which may have a fluorine atom and a divalent chain saturated hydrocarbon group which may have a fluorine atom It is a divalent alicyclic saturated hydrocarbon group, more preferably a perfluoroalkanediyl group. It is a aryl group. The divalent chain saturated hydrocarbon group which may have a fluorine atom includes a methylene group, an ethylene group, alkanediyl groups such as ethylene, propanediyl, butanediyl, and pentanediyl groups; ;Difluoromethylene group, perfluoroethylene group, perfluoropropanediyl group, perfluoroalkanes such as perfluorobutanediyl and perfluoropentanediyl groups Examples thereof include a diyl group. The divalent alicyclic saturated hydrocarbon group which may have a fluorine atom may be either monocyclic or polycyclic. The monocyclic group may be a cyclohexanediyl group or a perfluorocyclohexane group. Examples of the polycyclic group include an adamantanediyl group, a norbornanediyl group, and the like. Examples thereof include a nandiyl group and a perfluoroadamantanediyl group. A f14 The saturated hydrocarbon group and the saturated hydrocarbon group which may have a fluorine atom are R a42 in The same groups as those exemplified above can be mentioned. Among them, trifluoromethyl group, difluoromethyl group, ethyl 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 perfluorohexyl group. Fluorinated alkyl groups such as fluorooctyl groups, cyclopropylmethyl groups, cyclopropyl groups , cyclobutylmethyl group, cyclopentyl group, cyclohexyl group, perfluorocyclohexyl group xyl group, adamantyl group, adamantylmethyl group, adamantyldimethyl group, norbornyl group norbornyl group, norbornylmethyl group, perfluoroadamantyl group, perfluoroadamantine A methyl group is preferred.

[0172] In formula (a4-3), L 5 is preferably an ethylene group. A f13 The divalent saturated hydrocarbon group is a divalent chain saturated hydrocarbon group having 1 to 6 carbon atoms and a carbon A group containing a divalent alicyclic saturated hydrocarbon group having 3 to 12 carbon atoms is preferred, and a divalent chain having 2 to 3 carbon atoms is preferred. Saturated hydrocarbon groups of the formula are more preferred. A f14 The saturated hydrocarbon group is a chain saturated hydrocarbon group having 3 to 12 carbon atoms and a A group containing an alicyclic saturated hydrocarbon group such as the above is preferred, and a chain saturated hydrocarbon group having 3 to 10 carbon atoms and A group containing an alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms is more preferred. f14 teeth , preferably a group containing an alicyclic saturated hydrocarbon group having 3 to 12 carbon atoms, more preferably Cyclopropylmethyl group, cyclopentyl group, cyclohexyl group, norbornyl group and a It is a damantyl group.

[0173] Examples of the structural unit represented by formula (a4-3) include the structural units represented by formula (a4-1'-1) to formula (a 4-1'-11) are structural units represented by the following formulas. KerR f7 The structural unit in which the corresponding methyl group is replaced by a hydrogen atom is also represented by formula (a4-3). It is one of the structural units that can be mentioned.

[0174] The structural unit (a4) also includes a structural unit represented by formula (a4-4). TIFF2026027464000112.tif4466[In formula (a4-4), R f21 represents a hydrogen atom or a methyl group. A f21 is -(CH2) j1 -, -(CH2) j2 -O-(CH2) j3 -or-(CH2) j4 - CO-O-(CH2) j5 - represents. j1 to j5 each independently represent an integer of 1 to 6. R f22 represents a saturated hydrocarbon group having 1 to 10 carbon atoms and containing a fluorine atom.]

[0175] R f22 The saturated hydrocarbon group of R a42 The saturated hydrocarbon group may be the same as the saturated hydrocarbon group represented by the following formula: R f22 represents an alkyl group having 1 to 10 carbon atoms and a fluorine atom, or a carbon atom having a fluorine atom An alicyclic hydrocarbon group having 1 to 10 carbon atoms is preferred, and an alkyl group having 1 to 10 carbon atoms and a fluorine atom is preferred. A fluorine atom-containing alkyl group having 1 to 6 carbon atoms is more preferred.

[0176] In formula (a4-4), A f21 As -(CH2) j1 - is preferred, and ethylene A group or a methylene group is more preferred, and a methylene group is even more preferred.

[0177] Examples of the structural unit represented by formula (a4-4) include the following structural units and In the structural unit represented by R in the structural unit (a4-4) f21 The methyl group corresponding to Examples of structural units include those in which hydrogen atoms are replaced. JPEG2026027464000113.jpg80148

[0178] When the resin (A) contains the structural unit (a4), its content is the total of all structural units of the resin (A). Preferably, it is 1 to 20 mol %, more preferably 2 to 15 mol %, and more preferably 3 to 10 mol % is more preferable.

[0179] <Structural unit (a5)> The non-leaving hydrocarbon group contained in the structural unit (a5) may be a straight-chain, branched or cyclic hydrocarbon group. Among these, the structural unit (a5) is preferably a group having an alicyclic hydrocarbon group. The group is preferred. Examples of the structural unit (a5) include a structural unit represented by formula (a5-1): . TIFF2026027464000114.tif3971[In 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 water contained in the alicyclic hydrocarbon group The atom may be substituted with an aliphatic hydrocarbon group having 1 to 8 carbon atoms. L 55represents a single bond or a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, The —CH2— contained in the formula may be replaced with —O— or —CO—.

[0180] R 52 The alicyclic hydrocarbon group in may be either a monocyclic or polycyclic group. Examples of the alicyclic hydrocarbon group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclopentyl 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 a methyl group, an ethyl group, a propyl group, an isopropyl group, and an isopropyl group. Propyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group Examples of alkyl groups include an octyl group and a 2-ethylhexyl group. Examples of the alicyclic hydrocarbon group having a substituent include a 3-methyladamantyl group. do. R 52 is preferably an unsubstituted alicyclic hydrocarbon group having 3 to 18 carbon atoms, and more preferably Examples thereof include an adamantyl group, a norbornyl group, and a cyclohexyl group. L 55 The divalent saturated hydrocarbon group in the above is a divalent chain saturated hydrocarbon group and a divalent fatty acid group. Examples include cyclic saturated hydrocarbon groups, and preferably divalent chain saturated hydrocarbon groups. Examples of the divalent chain saturated hydrocarbon group include a methylene group, an ethylene group, and a propanediol group. alkanediyl groups such as butanediyl, pentanediyl, and the like. The divalent alicyclic saturated hydrocarbon group may be either monocyclic or polycyclic. Examples of saturated hydrocarbon groups include cyclopentanediyl and cyclohexanediyl groups. Examples of the polycyclic divalent alicyclic saturated hydrocarbon group include an adatom group. Examples include a mantanediyl group and a norbornanediyl group.

[0181] L 55 The -CH2- contained in the divalent saturated hydrocarbon group represented by is replaced by -O- or -CO-. Examples of the substituted groups include groups represented by formulae (L1-1) to (L1-4). In the following formula, * and ** each represent a bonding site, and * represents a bonding site with an oxygen atom. TIFF2026027464000115.tif18165 formula (L1-1), X x1 represents *-O-CO- or *-CO-O- (* represents 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, L x1 and L x2 The total number of carbon atoms is 16 or less. In formula (L1-2), L x3 represents a divalent aliphatic saturated hydrocarbon group having 1 to 17 carbon atoms. L x4 represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 16 carbon atoms. However, L x3 and L x4 The total number of carbon atoms is 17 or less. In formula (L1-3), L x5 represents a divalent aliphatic saturated hydrocarbon group having 1 to 15 carbon atoms. L x6 and L x7 are each independently a single bond or a divalent aliphatic saturated carbon atom having 1 to 14 carbon atoms. Represents a hydrogen group. However, L x5 , Lx6 and L x7 The total number of carbon atoms is 15 or less. In formula (L1-4), L x8 and L x9 represents a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 12 carbon atoms. W x1 represents a divalent alicyclic saturated hydrocarbon group having 3 to 15 carbon atoms. However, L x8 , L x9 and W x1 The total number of carbon atoms is 15 or less.

[0182] L x1 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably It is 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 Preferably, it is a single bond. L x3 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x4 is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms. L x5 is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably It is 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 Preferably, it is 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 Preferably, it is a single bond or a methylene group. L x9is preferably a single bond or a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, more preferably Preferably, it is 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.

[0183] Examples of the group represented by formula (L1-1) include the divalent groups shown below. TIFF2026027464000116.tif23135

[0184] TIFF2026027464000117.tif34117

[0185] Examples of the group represented by formula (L1-2) include the divalent groups shown below. TIFF2026027464000118.tif23130

[0186] Examples of the group represented by formula (L1-3) include the divalent groups shown below. TIFF2026027464000119.tif15147

[0187] Examples of the group represented by formula (L1-4) include the divalent groups shown below. TIFF2026027464000120.tif26114

[0188] L 55 is preferably a single bond or a group represented by formula (L1-1).

[0189] The structural unit (a5-1) includes the structural units shown below and the structural units ( R in a5-1) 51 The structural unit in which the methyl group corresponding to can be. TIFF2026027464000121.tif75150

[0190] TIFF2026027464000122.tif36151When resin (A) contains structural unit (a5), its content is the total of all structural units of resin (A). Preferably, it is 1 to 30 mol %, more preferably 2 to 20 mol %, and more preferably 3 to 15 mol % is more preferable.

[0191] <Structural unit (a6)> The structural unit (a6) is a structural unit having an -SO2- group, and has an -SO2- group in a side chain. It is preferable to do so. The structural unit having an -SO2- group may have a linear structure having an -SO2- group. Alternatively, it may have a branched structure having an -SO2- group, or a ring structure having an -SO2- group. It may have a ring structure (monocyclic or polycyclic structure). Preferably, it is a ring having an -SO2- group. It is a structural unit having a cyclic structure, and more preferably, a cyclic structure (sulfur) containing -SO2-O-. It is a structural unit that has a thion ring.

[0192] The sultone ring may be a ring having the following formula (T 1 -1), formula (T 1 -2), formula (T 1 -3) and formula ( T 1 The bonding site can be at any position. The sultone ring may be monocyclic, but is preferably polycyclic. means a bridged ring containing -SO2-O- as an atomic group constituting the ring, and the formula (T 1 -1 ) and formula (T 1 The sultone ring is represented by the formula (T 1 -2) In addition to -SO2-O-, the ring also contains heteroatoms. The heteroatom may include an oxygen atom, a sulfur atom, or a nitrogen atom. , preferably an oxygen atom. JPEG2026027464000123.jpg3187

[0193] The sultone ring may have a substituent, and the substituent may be a halogen atom or a hydroxy group. an alkyl group having 1 to 12 carbon atoms, which may have a halogen atom, a hydroxy group, a cyano group, groups, alkoxy groups having 1 to 12 carbon atoms, aryl groups having 6 to 12 carbon atoms, aryl groups having 7 to 12 carbon atoms Ralalkyl groups, glycidyloxy groups, alkoxycarbonyl groups having 2 to 12 carbon atoms, and Examples include alkylcarbonyl groups having 2 to 4 carbon atoms.

[0194] Halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. . The alkyl group includes a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and a methyl group. Examples of the alkyl group include a silyl group, an octyl group, and a decyl group, and preferably an alkyl group having 1 to 6 carbon atoms. More preferably, it is a methyl group. Examples of the alkyl group having a halogen atom include a trifluoromethyl group, a perfluoroethyl group, and a methyl group. perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, Perfluorosec-butyl group, perfluorotert-butyl group, perfluoropentyl perfluorohexyl, trichloromethyl, tribromomethyl and triiodomethyl groups. A trifluoromethyl group is preferred. Examples of alkyl groups having a hydroxy group include a hydroxymethyl group and a 2-hydroxyethyl group. Examples of the hydroxyalkyl group include a hydroxyalkyl group having a methyl group. The alkoxy group includes a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, and the like. hydroxyl group, hexyloxy group, heptyloxy group, octyloxy group, decyloxy group and dodecyloxy groups. The aryl group includes a phenyl group, a naphthyl group, an anthryl group, and a p-methylphenyl group. , p-tert-butylphenyl group, p-adamantylphenyl group, tolyl group, xylyl group group, cumyl group, mesityl group, biphenyl group, phenanthryl group, 2,6-diethylphenyl group Examples include the phenyl group and the 2-methyl-6-ethylphenyl group. Examples of the aralkyl group include a benzyl group, a phenethyl group, a phenylpropyl group, a naphthylmethyl group, and the like. Examples include ethyl and naphthylethyl groups. Examples of the alkoxycarbonyl group include a methoxycarbonyl group and an ethoxycarbonyl group. Examples include a group in which an alkoxy group and a carbonyl group are bonded, and preferably an alkoxy group having 6 or less carbon atoms. An example thereof is an oxycarbonyl group, and more preferably a methoxycarbonyl group. Examples of the alkylcarbonyl group include an acetyl group, a propionyl group, and a butyryl group. can be.

[0195] From the viewpoint of ease of production of the monomer from which the structural unit (a6) is derived, A sultone ring is preferred. The sultone ring is preferably a ring represented by the following formula (T1'). JPEG2026027464000124.jpg3172[In formula (T1'), X 11 represents an oxygen atom, a sulfur atom or a methylene group. R 41 is an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group. alkyl groups, halogen atoms, hydroxy groups, cyano groups, alkoxy groups with 1 to 12 carbon atoms, Aryl groups having 6 to 12 carbon atoms, aralkyl groups having 7 to 12 carbon atoms, glycidyloxy groups, and groups having 2 carbon atoms. It represents an alkoxycarbonyl group having from 1 to 12 carbon atoms or an alkylcarbonyl group having from 2 to 4 carbon atoms. ma represents an integer of 0 to 9. When ma is 2 or more, multiple R 41 are identical It may be the same or different. The binding site is at any position.] X 11 is preferably an oxygen atom or a methylene group, more preferably a methylene group. do. R 41 Examples of the substituents include the same as those of the sultone ring, and include a halogen atom or a hydroxyl group. An alkyl group having 1 to 12 carbon atoms which may have an alkoxy group is preferred.

[0196] The sultone ring is more preferably a ring represented by formula (T1). JPEG2026027464000125.jpg3149 [In formula (T1), R 8 is an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group. groups, halogen atoms, hydroxy groups, cyano groups, alkoxy groups having 1 to 12 carbon atoms, and alkoxy groups having 6 carbon atoms Aryl groups having 7 to 12 carbon atoms, aralkyl groups having 7 to 12 carbon atoms, glycidyloxy groups, and groups having 2 to 12 carbon atoms. 12 alkoxycarbonyl group or alkylcarbonyl group having 2 to 4 carbon atoms. m represents an integer of 0 to 9. When m is 2 or more, a plurality of R 8 are identical and may also be different. The binding site is at any position.]

[0197] R 8 is R 41 The same can be mentioned. ma in formula (T1') and m in formula (T1) are preferably 0 or 1, More preferably, it is 0.

[0198] Examples of the ring represented by formula (T1') and the ring represented by formula (T1) include the following rings: The binding site is at an arbitrary position. JPEG2026027464000126.jpg46145

[0199] The structural unit having a sultone ring preferably has the following group: * in the following group represents the binding site. JPEG2026027464000127.jpg46142

[0200] The structural unit having a -SO2- group preferably further has a group derived from a polymerizable group. The polymerizable group may be a vinyl group, an acryloyl group, a methacryloyl group, an acryloyl group, or a methyl group. Oxy group, methacryloyloxy group, acryloylamino group, methacryloylamino group, Examples include an acryloylthio group and a methacryloylthio group. Among them, the monomer from which the structural unit (a6) is derived is preferably a monomer having an ethylenically unsaturated bond. It is preferably a monomer having a (meth)acrylic group, and more preferably a (meth)acrylic monomer.

[0201] The structural unit (a6) is preferably a structural unit represented by formula (Ix). JPEG2026027464000128.jpg4956 [In formula (Ix), R x represents an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, represents an atomic atom or a halogen atom. A xx is 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- is -O-, -CO- or -N(R d )- may be replaced. X 11 represents an oxygen atom, a sulfur atom or a methylene group. R 41 is an alkyl group having 1 to 12 carbon atoms which may have a halogen atom or a hydroxy group. alkyl groups, halogen atoms, hydroxy groups, cyano groups, alkoxy groups with 1 to 12 carbon atoms, Aryl groups having 6 to 12 carbon atoms, aralkyl groups having 7 to 12 carbon atoms, glycidyloxy groups, and groups having 2 carbon atoms. It represents an alkoxycarbonyl group having from 1 to 12 carbon atoms or an alkylcarbonyl group having from 2 to 4 carbon atoms. ma represents an integer of 0 to 9. When ma is 2 or more, multiple R 41 are identical It may be the same or different. R c and R d each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.

[0202] R x Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. can be done. R x Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and the like. butyl group, n-butyl group, sec-butyl group, tert-butyl group, n-pentyl group and n -hexyl group, etc., and is preferably an alkyl group having 1 to 4 carbon atoms, and more preferably is a methyl group or an ethyl group. R x Examples of the alkyl group having a halogen atom include a trifluoromethyl group, a phenyl group, and a phenyl group. perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluoro perfluorobutyl group, perfluorosec-butyl group, perfluorotert-butyl group, perfluoro Fluoropentyl group, perfluorohexyl group, trichloromethyl group, tribromomethyl group group and triiodomethyl group. R x is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and more preferably a hydrogen atom. It is preferably a hydrogen atom, a methyl group, or an ethyl group, and more preferably a hydrogen atom or a methyl group.

[0203] A x The divalent saturated hydrocarbon group includes a linear alkanediyl group, a branched alkanediyl group, and and monocyclic or polycyclic divalent alicyclic saturated hydrocarbon groups. It may be a combination of more than one species. Specifically, methylene group, ethylene group, propane-1,3-diyl group, propane-1, 2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1 ,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane- 1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group Decane-1,12-diyl group, tridecane-1,13-diyl group, tetradecane-1,1 4-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- linear alkanediyl groups such as diyl and propane-2,2-diyl groups; Butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane Pan-1,2-diyl group, pentane-1,4-diyl group, 2-methylbutane-1,4-diyl group branched alkanediyl groups such as alkanediyl groups; Cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohexa cycloalkanediyl groups such as cyclohexene-1,4-diyl and cyclooctane-1,5-diyl a monocyclic divalent alicyclic saturated hydrocarbon group; Norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane- Polycyclic divalent alicyclic saturated carbons such as 1,5-diyl and adamantane-2,6-diyl groups Examples include a hydrogen group.

[0204] R 41 , X 11 and ma may be the same as those in formula (T1'). Examples of the sultone ring include those mentioned above, and among them, those mentioned above in which the bonding position is specified are It is preferable that:

[0205] Examples of the structural unit (a6) include the following structural units. JPEG2026027464000129.jpg92150

[0206] Among them, formula (a6-1), formula (a6-2), formula (a6-6), formula (a6-7), formula ( The structural units represented by the formula (a6-8) and formula (a6-12) are preferred, and the structural units represented by the formula (a6-1) and formula (a6-2) are preferred. a6-2), and structural units represented by formulae (a6-7) and (a6-8) are more preferred. When the resin (A) has the structural unit (a6), its content is determined based on the total structural units of the resin (A). The ratio is preferably 1 to 50 mol %, more preferably 2 to 40 mol %, and more preferably 3 to 30 mol % is more preferred.

[0207] <Structural unit (II)> The resin (A) further contains a structural unit that decomposes upon exposure to generate an acid (hereinafter, “structural unit”). The structural unit (II) may specifically include is a structural unit described in JP-A-2016-79235, and has a sulfonate group in the side chain. or a structural unit having a carboxylate group and an organic cation or a sulfonio group on a side chain and an organic anion.

[0208] A structural unit having a sulfonate group or a carboxylate group and an organic cation in the side chain is preferably a structural unit represented by formula (II-2-A'). TIFF2026027464000130.tif35104[In formula (II-2-A'), X III3 represents a divalent saturated hydrocarbon group having 1 to 18 carbon atoms, and the saturated hydrocarbon group The -CH2- contained in the saturated carbon may be replaced by -O-, -S- or -CO-. The hydrogen atom contained in the hydrogen hydride group is a halogen atom, a carbon number which may have a halogen atom It may be substituted with 1 to 6 alkyl groups or hydroxy groups. A x1 represents an alkanediyl group having 1 to 8 carbon atoms, and the water contained in the alkanediyl group The atom may be substituted with a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms. stomach. RA - represents a sulfonate group or a carboxylate group. R III3 is a hydrogen atom, a halogen atom, or a group having 1 carbon atom which may have a halogen atom Represents an alkyl group of 1 to 6. ZA + represents an organic cation.

[0209] R III3 Examples of the halogen atom represented by the formula include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples include uron atoms. R III3 The alkyl group having 1 to 6 carbon atoms and optionally having a halogen atom is represented by the formula: R a8The same as an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, represented by Examples include the same things. A x1 Examples of the alkanediyl group having 1 to 8 carbon atoms represented by the formula (I) include a methylene group, an ethylene group, and the like. , propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group group, hexane-1,6-diyl group, 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 Examples thereof include a pentane-1,4-diyl group, a 2-methylbutane-1,4-diyl group, and the like. do. A x1 In the above, the perfluoroalkyl group having 1 to 6 carbon atoms which may be substituted is , trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoro perfluoroisopropyl group, perfluorobutyl group, perfluorosec-butyl group, perfluorotetrafluoroethylene group Examples include a rt-butyl group, a perfluoropentyl group, and a perfluorohexyl group. X III3 The divalent saturated hydrocarbon group having 1 to 18 carbon atoms represented by the formula (I) is a straight-chain or branched hydrocarbon group. and monocyclic or polycyclic divalent alicyclic saturated hydrocarbon groups. It may be a combination of the above. Specifically, methylene group, ethylene group, propane-1,3-diyl group, propane-1, 2-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane-1 ,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, nonane- 1,9-diyl group, decane-1,10-diyl group, undecane-1,11-diyl group, dodecane-1,12-diyl group linear alkanediyl groups such as decane-1,12-diyl; butane-1,3-diyl; 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentaerythritol Branched alkanediyl groups such as 2-methylbutane-1,4-diyl group, 2-methylbutane-1,4-diyl group cyclobutane-1,3-diyl group, cyclopentane-1,3-diyl group, cyclohetane-1,3-diyl group, Cycloalkanediyl groups such as cyclohexan-1,4-diyl group and cyclooctane-1,5-diyl group norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane Divalent polycyclic alicyclic saturated carbons such as benzophenone-1,5-diyl and adamantane-2,6-diyl groups Examples thereof include a hydrogen hydride group. -CH2- in saturated hydrocarbon groups is replaced with -O-, -S- or -CO- Examples of such groups include divalent groups represented by formulae (X1) to (X53). The -CH2- contained in the saturated hydrocarbon group is replaced with -O-, -S- or -CO-. The number of carbon atoms in each of the preceding groups is 17 or less. In the following formula, * and ** represent binding sites. * is A x1 represents the binding site with JPEG2026027464000131.jpg145161

[0210] 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.

[0211] ZA in formula (II-2-A') + is the cation Z1 in the salt represented by formula (B1) + The same can be mentioned.

[0212] The structural unit represented by formula (II-2-A') is a structural unit represented by formula (II-2-A) It is preferable that: TIFF2026027464000132.tif38109 [In formula (II-2-A), R III3 , X III3 and ZA + has the same meaning as above. z2A represents an integer of 0 to 6. R III2 and R III4 are each independently a hydrogen atom, a fluorine atom, or a group having 1 carbon atom represents a perfluoroalkyl group having a number of 1 to 6, and 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 are each independently a fluorine atom or a perfluoroalkane having 1 to 6 carbon atoms. represents a alkyl group.] R III2 , R III4 , Q a and Q b Perfluoroalkyl groups having 1 to 6 carbon atoms, represented by As the aryl group, the aforementioned Q b1 The same as the perfluoroalkyl group having 1 to 6 carbon atoms represented by Examples include:

[0213] The structural unit represented by formula (II-2-A) is a structural unit represented by formula (II-2-A-1). It is preferable that the position is . TIFF2026027464000133.tif5577 [In formula (II-2-A-1), R III2 , R III3 , R III4 , Q a , Q b and ZA + means the same as above . R III5 represents a saturated hydrocarbon group having 1 to 12 carbon atoms. z2A1 represents an integer of 0 to 6. X I2 represents a divalent saturated hydrocarbon group having 1 to 11 carbon atoms, and the saturated hydrocarbon group -CH2- may be replaced by -O-, -S- or -CO-, and the saturated hydrocarbon The hydrogen atoms contained in the alkyl group may be substituted with halogen atoms or hydroxy groups. R III5 Examples of the saturated hydrocarbon group having 1 to 12 carbon atoms represented by the formula include a methyl group, an ethyl group, and , propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, butyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group and and dodecyl groups. X I2 As the divalent saturated hydrocarbon group represented by X III3 Divalent saturated carbon represented by The same as the hydrogen chloride group can be mentioned.

[0214] The structural unit represented by formula (II-2-A-1) is preferably a structural unit represented by formula (II-2-A-2). The structural unit is preferably TIFF2026027464000134.tif5187 [In formula (II-2-A-2), R III3 , R III5 and ZA + has the same meaning as above. m and nA each independently represent 1 or 2.

[0215] Examples of the structural unit represented by formula (II-2-A') include the following structural units, R III3 The group corresponding to the methyl group is a hydrogen atom, a halogen atom (e.g., a fluorine atom), or a halogen atom an alkyl group having 1 to 6 carbon atoms which may have one or more atoms (for example, a trifluoromethyl group, etc.); The structural units replaced by the above and the structural units described in WO 2012 / 050015 are listed. It can be obtained. ZA + represents an organic cation. JPEG2026027464000135.jpg86163

[0216] The structural unit having a sulfonio group and an organic anion in the side chain is represented by formula (II-1-1): It is preferable that the structural unit is a structural unit that can be formed by the above-mentioned method. TIFF2026027464000136.tif3791 [In 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 represents a hydrocarbon group having 1 to 18 carbon atoms; R II2 and R II3 are bonded to each other to form a ring with the sulfur atom to which they are attached. That's fine. R II4 is a hydrogen atom, a halogen atom, or a group having 1 to 6 carbon atoms which may have a halogen atom represents an alkyl group represented by the formula: A - represents an organic anion. R II1 Examples of the divalent aromatic hydrocarbon group having 6 to 18 carbon atoms represented by the formula (I) include a phenylene group. and naphthylene groups. R II2 and RII3 Examples of the hydrocarbon group represented by the formula (I) include an alkyl group and an alicyclic hydrocarbon group. , aromatic hydrocarbon groups, and groups formed by combining these groups. Examples of the alkyl group and the alicyclic hydrocarbon group include the same as those described above. Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, Examples include aryl groups such as a phenanthryl group. The combined group may be a group in which the above-mentioned alkyl group and alicyclic hydrocarbon group are combined. , aralkyl groups such as benzyl groups, aromatic hydrocarbon groups having alkyl groups (p-methylphenyl nyl group, p-tert-butylphenyl group, tolyl group, xylyl group, cumenyl group, mesityl group phenyl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group, etc.), alicyclic carbon Aromatic hydrocarbon groups containing hydrogen hydride groups (p-cyclohexylphenyl group, p-adamantyl phenyl group, phenylcyclohexyl group, and other aryl-cycloalkyl groups. can be. R II4 Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodide atom. Examples include elementary atoms. R II4 As an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, represented by is R a8 The same as the alkyl group having 1 to 6 carbon atoms which may have a halogen atom, represented by Some examples include: A II1 Examples of the divalent linking group represented by the formula (I) include a divalent saturated carbon atom having 1 to 18 carbon atoms. The -CH2- contained in the divalent saturated hydrocarbon group may be -O-, -S- or may be replaced by -CO-. Specifically, X III3 The number of carbon atoms is 1 to 1 Examples thereof include the same divalent saturated hydrocarbon groups as those of 8.

[0217] The structural unit containing a cation in formula (II-1-1) includes the structural units represented by the following formulas: BiR II4 The group corresponding to the methyl group in the formula (I) is a hydrogen atom, a halogen atom (e.g., a fluorine atom), or is an alkyl group having 1 to 6 carbon atoms which may have a halogen atom (for example, trifluoromethyl Examples include structural units in which the methyl group is replaced by a methyl group, etc. JPEG2026027464000137.jpg84130

[0218] A - Examples of the organic anion represented by the formula include a sulfonate anion, a sulfonylimide anion, and Examples of the anion include sulfonylmethide anion, carboxylate anion, and the like. - is expressed as The organic anion is preferably a sulfonate anion. It is more preferable that the anion is an anion contained in the salt represented by formula (B1). The carboxylate anion, sulfonylmethide anion and carboxylate anion are represented by the above formula (I). The anion AI contained in the salt - It is more preferable that:

[0219] Examples of the structural unit represented by formula (II-1-1) include the structural units represented by the following formula: can be done. JPEG2026027464000138.jpg88149

[0220] When the structural unit (II) is contained in the resin (A), the content of the structural unit (II) is It is preferably 1 to 20 mol %, more preferably 2 to 30 mol %, based on the total structural units of the fat (A). It is 15 mol %, and more preferably 3 to 10 mol %.

[0221] The resin (A) may contain structural units other than the above-mentioned structural units. The moieties include structural units known in the art.

[0222] The resin (A) is preferably a resin comprising the structural unit (a1) and the structural unit (s), i.e., That is, it is a copolymer of the monomer (a1) and the monomer (s). The structural unit (a1) is preferably a structural unit (a1-0), a structural unit (a1-1) and a structural unit (a1-2). The structural unit (a1-2) (preferably the structural unit having a cyclohexyl group or a cyclopentyl group) At least one selected from the group consisting of structural units, more preferably at least two selected from the group consisting of and more preferably, the group consisting of the structural unit (a1-1) and the structural unit (a1-2). At least two selected from the above. The structural unit (s) is preferably selected from the group consisting of the structural unit (a2) and the structural unit (a3): The structural unit (a2) is preferably at least one selected from the structural unit (a2-1). The structural unit (a3) ​​is preferably a structural unit (a2-A) represented by the formula (a3-1): a structural unit represented by formula (a3-2) and a structural unit represented by formula (a3-4) It is at least one selected from the group consisting of units. The structural units constituting the resin (A) may be used singly or in combination of two or more. Instead, monomers that lead to these structural units are used in known polymerization methods (for example, radical polymerization methods). The content of each structural unit contained in the resin (A) can be determined by the following procedure. It can be adjusted by the amount of monomer used. The weight average molecular weight of the resin (A) is preferably 2,000 or more (more preferably 2,500 or more). 00 or more, more preferably 3,000 or more), 50,000 or less (more preferably 30 In this specification, the weight average molecular weight is 1,000 or less, and more preferably 15,000 or less. The molecular weight is determined by gel permeation chromatography under the conditions described in the examples. is.

[0223] <Resins other than Resin (A)> The resist composition of the present invention may contain a resin other than the resin (A) in combination. Examples of resins other than the resin (A) include those containing the structural unit (a4) or the structural unit (a5). Examples of the resin include a resin having the above structure (hereinafter, sometimes referred to as resin (X)). As the resin (X), a resin containing the structural unit (a4) is particularly preferred. In resin (X), the content of structural unit (a4) is the sum of all structural units in resin (X). It is preferably 30 mol % or more, more preferably 40 mol % or more. It is more preferable that the content is 45 mol % or more. Examples of structural units that the resin (X) may further have include the structural unit (a1), the structural unit (a2), structural unit (a3), and structural units derived from other known monomers. Among these, the resin (X) is preferably composed only of the structural unit (a4) and / or the structural unit (a5). It is preferably a resin. The structural units constituting the resin (X) may be used alone or in combination of two or more. Using monomers that derive these structural units, a known polymerization method (e.g., radical polymerization method) can be used. The content of each structural unit in the resin (X) can be determined by the following procedure. It can be adjusted by the amount of monomer used. The weight average molecular weight of the resin (X) is preferably 6,000 or more (more preferably 7,000 or more). 0 or more) and 80,000 or less (more preferably 60,000 or less). The weight average molecular weight can be measured by the same method as in the case of resin (A).

[0224] When the resist composition of the present invention contains resin (X), the content of resin (X) is 100% by weight of resin (A). The amount is preferably 1 to 60 parts by mass, more preferably 1 to 50 parts by mass, based on the total mass of the hydroxybenzoates. It is more preferably 1 to 40 parts by mass, and even more preferably 1 to 30 parts by mass. More preferably, it is 1 to 8 parts by mass.

[0225] The content of resin (A) in the resist composition is 8% by weight based on the solid content of the resist composition. It is preferably 0% by mass or more and 99% by mass or less, and more preferably 90% by mass or more and 99% by mass or less. In addition, when a resin other than the resin (A) is contained, the resin (A) and the resin other than the resin (A) are preferably mixed. The total content of the resin is 80% by mass or more and 99% by mass or less of the solid content of the resist composition. It is preferable that the content is 90% by mass or less and more preferably 90% by mass or less and 99% by mass or less. In this context, the "solid content of the resist composition" refers to the amount of the solvent (E The solid content of the resist composition and the resin content The rate is measured by known analytical means such as liquid chromatography or gas chromatography. It is possible.

[0226] <Solvent (E)> The content of the solvent (E) in the resist composition is usually 90% by mass or more and 99.9% by mass or less. It is preferably 92% by mass or more and 99% by mass or less, and more preferably 94% by mass or more. The content of the solvent (E) is 99% by mass or less. The content of the solvent (E) is measured by, for example, liquid chromatography or gas chromatography. It can be measured by known analytical means such as chromatography.

[0227] The solvent (E) may be ethyl cellosolve acetate, methyl cellosolve acetate, or Glycol ether esters such as propylene glycol monomethyl ether acetate ; Glycol ethers such as propylene glycol monomethyl ether; Ethyl lactate, acetic acid esters such as butyl acetate, amyl acetate and ethyl pyruvate; acetone, methyl isobutyl esters; ketones such as cyclohexanone, 2-heptanone, and cyclohexanone; γ-butyrolactone; cyclic esters; etc. One type of solvent (E) may be used alone, Two or more types may be used.

[0228] <Quencher (C)> The quencher (C) is a basic nitrogen-containing organic compound and an acid generated from an acid generator. The resist composition may include a salt that generates an acid having a weaker acidity than the quencher (C). In the case where the resist composition contains the quencher (C), the content of the quencher (C) is determined based on the solid content of the resist composition. It is preferably about 0.01 to 15% by mass, and more preferably about 0.01 to 10% by mass. is more preferable, and about 0.1 to 8 mass% is even more preferable, and 0.1 to 7 mass% It is even more preferable that the amount is about 1000 .mu.m. Examples of basic nitrogen-containing organic compounds include amines and ammonium salts. The amines include aliphatic amines and aromatic amines. The aliphatic amines include primary amines, Amines include secondary amines and tertiary amines.

[0229] Amines include 1-naphthylamine, 2-naphthylamine, aniline, and diisopropylamine. aniline, 2-, 3- or 4-methylaniline, 4-nitroaniline, N-methylaniline Phosphorus, N,N-dimethylaniline, diphenylamine, hexylamine, heptylamine , octylamine, nonylamine, decylamine, dibutylamine, dipentylamine, Dihexylamine, diheptylamine, dioctylamine, dinonylamine, didecylamine amine, triethylamine, trimethylamine, tripropylamine, tributylamine, Tripentylamine, trihexylamine, triheptylamine, trioctylamine, Trinonylamine, tridecylamine, methyldibutylamine, methyldipentylamine , methyldihexylamine, methyldicyclohexylamine, methyldiheptylamine, Methyldioctylamine, Methyldinonylamine, Methyldidecylamine, Ethyldibutylamine diamine, ethyldipentylamine, ethyldihexylamine, ethyldiheptylamine , ethyldioctylamine, ethyldinonylamine, ethyldidecylamine, dicyclohexane xylmethylamine, tris[2-(2-methoxyethoxy)ethyl]amine, triisopropylamine Propanolamine, ethylenediamine, tetramethylenediamine, hexamethylenediamine amine, 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'-dipyridyl sulfide, 4,4'-dipyridyl disulfide Examples include phenanthroline, 2,2'-dipyridylamine, 2,2'-dipicolylamine, bipyridine, etc., preferably diisopropylaniline, more preferably 2,6-diisopropylaniline. Examples of the ammonium salts include tetramethylammonium hydroxide, tetraisopropylammonium hydroxide, tetrabutylammonium hydroxide, tetrahexylammonium hydroxide, tetraoctylammonium hydroxide, phenyltrimethylammonium hydroxide, 3-(trifluoromethyl)phenyltrimethylammonium hydroxide, tetra-n-butylammonium salicylate, choline, etc.

[0230] The acidity of a salt that generates an acid with a lower acidity than the acid generated from the acid generator 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 is a salt with an acid dissociation constant of the acid generated from the salt usually being -3 < pKa, preferably -1 < pKa < 7, more preferably 0 < pKa < 5. Examples of the salt that generates an acid with a lower acidity than the acid generated from the acid generator 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 intramolecular 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 is preferably an acid generated from the acid generator.

[0231] The acidity of a salt that generates an acid with a lower acidity than the acid generated from the acid generator 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 is a salt with an acid dissociation constant of the acid generated from the salt usually being -3 < pKa. Preferably, it is 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 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 intramolecular salt (D)"), and salts described in JP-A-2012-229206, JP-A-2012-6908, JP-A-2012-72109, JP-A-2011-3950 2, and JP-A-2011-191745. The salt that generates an acid with a lower acidity than the acid generated from the acid generator is preferably an acid generated from the acid generator. Examples of the salt that generates an acid with a lower acidity than the acid generated from the acid generator 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 intramolecular salt (D)"), and salts described in JP-A-2012-229206, JP-A-2012-6908, JP-A-2012-72109, JP-A-2011-3950 Examples of the salt that generates an acid with a lower acidity than the acid generated from the acid generator 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 intramolecular salt (D)"), and salts described in JP-A-2012-229206, JP-A-2012-6908, JP-A-2012-72109, JP-A-2011-3950 It is a salt that generates a carboxylic acid with a weaker acidity than the carboxylic acid salt (a salt having a carboxylic acid anion). More preferably, it is a weak acid inner salt (D), and even more preferably, it is a weak acid inner salt (D). The carboxylic acid anion is a diphenyliodonium salt containing a substituted phenyl group. . JPEG2026027464000139.jpg120168

[0232] As the weak acid inner salt (D), there is an iodonium cation with two phenyl groups bonded to it, At least one of the two phenyl groups bonded to the iodonium cation and a diphenyliodonium salt having a substituted carboxylic acid anion. Examples of suitable salts include those represented by the following formulas:

[0233] JPEG2026027464000140.jpg2362[In formula (D), R D1 and R D2 are each independently a hydrocarbon group having 1 to 12 carbon atoms, an alkyl group having 1 to 6 carbon atoms, oxy group, acyl group having 2 to 7 carbon atoms, acyloxy group having 2 to 7 carbon atoms, acyl group having 2 to 7 carbon atoms represents a alkoxycarbonyl group, a nitro group or a halogen atom. m' and n' each independently represent an integer of 0 to 4, and when m' is 2 or more, In this case, multiple R D1 may be the same or different, and when n' is 2 or more, a plurality of R D2 The same They may be the same or different.] R D1 and R D2 The hydrocarbon group may be a chain hydrocarbon group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group, or the like. Examples include hydrogen groups and groups formed by combining these groups. Examples of the chain hydrocarbon group include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group. alkyl groups such as isobutyl, tert-butyl, pentyl, hexyl, and nonyl groups Examples of such groups include aryl groups. The alicyclic hydrocarbon group may be either monocyclic or polycyclic, and may be either saturated or unsaturated. Any of the following may be used: a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group group, a cycloalkyl group such as a cyclononyl group or a cyclododecyl group, a norbornyl group, an adamantan group Examples include a methyl group. Aromatic hydrocarbon groups include phenyl, 1-naphthyl, 2-naphthyl, and 2-methyl groups. phenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, 4-propylphenyl group, 4-isopropylphenyl group, 4-butylphenyl group, 4-t -butylphenyl group, 4-hexylphenyl group, 4-cyclohexylphenyl group, anthracene p-adamantylphenyl, tolyl, xylyl, cumenyl, mesityl , biphenyl group, phenanthryl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group and aryl groups such as phenyl groups. Examples of groups formed by combining these include alkyl-cycloalkyl groups. , cycloalkyl-alkyl groups, aralkyl groups (e.g., phenylmethyl groups, 1-phenyl ethyl group, 2-phenylethyl group, 1-phenyl-1-propyl group, 1-phenyl-2 -propyl group, 2-phenyl-2-propyl group, 3-phenyl-1-propyl group, 4-phenyl- phenyl-1-butyl group, 5-phenyl-1-pentyl group, 6-phenyl-1-hexyl group etc.) Examples of the alkoxy group include a methoxy group and an ethoxy group. The acyl group includes an acetyl group, a propanoyl group, a benzoyl group, a cyclohexane group, and Examples include a hydroxyl group. Examples of the acyloxy group include a group in which an oxy group (—O—) is bonded to the above-mentioned acyl group. can be. The alkoxycarbonyl group is an alkoxy group bonded to a carbonyl group (—CO—). Examples of such groups include a group obtained by combining two or more groups. Examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom. R D1 and R D2 are each independently an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, alkyl groups, alkoxy groups having 1 to 6 carbon atoms, acyl groups having 2 to 4 carbon atoms, an acyloxy group, an alkoxycarbonyl group having 2 to 4 carbon atoms, a nitro group, or a halogen atom preferable. Preferably, m' and n' are each independently an integer of 0 to 2, and 0 When m' is 2 or more, a plurality of R D1 are the same but different If n' is 2 or more, multiple R D2 may be the same or different.

[0234] More specifically, the following salts are included: TIFF2026027464000141.tif72165

[0235] <Other ingredients> The resist composition of the present invention may contain components other than the above-mentioned components (hereinafter referred to as "other components") as needed. It may contain other ingredients (F). The resist composition may contain additives known in the resist field, such as sensitizers, dissolution inhibitors, surfactants, stabilizers, etc. Agents, dyes, etc. can be used.

[0236] <Preparation of Resist Composition> The resist composition of the present invention comprises a salt (I) and a resin (A), and, if necessary, an acid generating Agent (B), resin other than resin (A), solvent (E), quencher (C) and other components ( F). The order of mixing is arbitrary and is not particularly limited. The temperature when mixing varies from 10 to 40°C depending on the type of resin, solvent, etc. The appropriate temperature can be selected depending on the solubility of the compound in E). Depending on the situation, an appropriate time can be selected from 0.5 to 24 hours. There is no limitation on the method, and stirring and mixing can be used. After mixing the components, filter the mixture using a filter with a pore size of approximately 0.003 to 0.2 μm. It is preferable that

[0237] <Method for Producing Resist Pattern> The method for producing a resist pattern of the present invention comprises the steps of: (1) applying the resist composition of the present invention onto a substrate; (2) drying the applied composition to form a composition layer; (3) exposing the composition layer to light; (4) heating the composition layer after exposure; and (5) A step of developing the composition layer after heating is included. To apply the resist composition to the substrate, a commonly used device such as a spin coater is used. The substrate may be an inorganic substrate such as a silicon wafer, or a substrate having a resist on the surface. Before applying the resist composition, the substrate is washed. An anti-reflection film or the like may be formed on the substrate. The composition after coating is dried to remove the solvent and form a composition layer. For example, the solvent can be evaporated using a heating device such as a hot plate (prebaking). The heating temperature is 50 to 200°C. The heating time is preferably 10 to 180 seconds. The pressure during this process is 1 to 1.0 x 10 5 It is preferable that the pressure is about Pa. The resulting composition layer is usually exposed using an exposure machine. The exposure light source may be a KrF excimer laser (wavelength 248 nm), an ArF excimer Lasers in the ultraviolet range such as F2 excimer laser (wavelength 193 nm) and F2 excimer laser (wavelength 157 nm) Laser light emitted from a solid-state laser light source (YAG or semiconductor laser, etc.) Those that convert wavelength and emit harmonic laser light in the far ultraviolet or vacuum ultraviolet range, electron beams, Various types of light sources can be used, such as those that irradiate ultraviolet light (EUV). In this case, the irradiation of these radiations is sometimes collectively called "exposure". The exposure is usually carried out through a mask corresponding to the desired pattern. In the case of lines, exposure may be performed by direct writing without using a mask. The composition layer after exposure is subjected to a heat treatment (i.e., a heat treatment) to promote the deprotection reaction of the acid labile groups. The heating temperature is usually about 50 to 200°C, preferably The temperature is preferably about 70 to 150°C. The hydrophilicity or hydrophobicity of the resin on the surface side of the composition after heating A chemical treatment (silylation) to adjust the film properties may be carried out. The steps of applying a resist composition, drying, exposing, and heating may be repeated on the composition layer. The composition layer after heating is usually developed using a developing device and a developer. Examples of methods include the dip method, puddle method, spray method, and dynamic dispense method. The development temperature is preferably, for example, 5 to 60°C, and the development time is, for example, 5 The time is preferably 300 seconds or less. By selecting the type of developer as follows: Either a positive resist pattern or a negative resist pattern can be produced. When a positive resist pattern is produced from the resist composition of the present invention, a developer An alkaline developer is used. The alkaline developer is a type of alkaline water used in this field. Any solution is acceptable. For example, tetramethylammonium hydroxide or (2-hydroxy Examples include an aqueous solution of ethyl)trimethylammonium hydroxide (commonly known as choline). The alkaline developer may contain a surfactant. After development, the resist pattern is washed with ultrapure water, and then the water remaining on the substrate and pattern is removed. It is preferable to remove it. When a negative resist pattern is produced from the resist composition of the present invention, a developer A developer containing an organic solvent (hereinafter sometimes referred to as an "organic developer") is used. The organic solvents contained in organic developers include ketones such as 2-hexanone and 2-heptanone. Glycol ether solvents such as propylene glycol monomethyl ether acetate Ester solvents such as butyl acetate; propylene glycol monomethyl ether, etc. Glycol ether solvents; amide solvents such as N,N-dimethylacetamide; anisole and aromatic hydrocarbon solvents such as the above. In the organic developer, the content of the organic solvent is preferably 90% by mass or more and 100% by mass or less, The content is more preferably 95% by mass or more and 100% by mass or less, and more preferably substantially only an organic solvent. More preferable. Among them, organic developers include developers containing butyl acetate and / or 2-heptanone. In the organic developer, the total content of butyl acetate and 2-heptanone is preferably 50% by mass. Preferably, the content is 90% by mass or more and 100% by mass or less, more preferably 90% by mass or more and 100% by mass or less. It is more preferable that the mixture is qualitatively only butyl acetate and / or 2-heptanone. The organic developer may contain a surfactant. The water content may be less than 100%. During development, development is stopped by replacing the organic developer with a different type of solvent. Good too. After development, the resist pattern is preferably washed with a rinse solution. There are no particular restrictions as long as the solvent does not dissolve the resist pattern, and solvents including general organic solvents are also usable. A solvent can be used, preferably an alcohol solvent or an ester solvent. After cleaning, it is preferable to remove the rinse liquid remaining on the substrate and the pattern.

[0238] <Application> The resist composition of the present invention is a resist composition for exposure to KrF excimer laser, ArF excimer laser, Resist composition for exposure to ultraviolet laser, resist composition for exposure to electron beam (EB) or EU resist compositions for V exposure, particularly resist compositions for electron beam (EB) exposure or EUV exposure The composition is suitable as a resist composition for semiconductors and is useful for microfabrication of semiconductors. [Example]

[0239] The present invention will be explained in more detail with reference to examples. "%" and "parts" are by weight unless otherwise specified. The weight average molecular weight is a value determined by gel permeation chromatography. The analytical conditions for gel permeation chromatography are as follows: Column: TSKgel Multipore HXL-M x 3 + guard column (Tosoh Corporation) Eluent: tetrahydrofuran Flow rate: 1.0mL / min Detector: RI detector Column temperature: 40℃ Injection volume: 100μl Molecular weight standard: Standard polystyrene (Tosoh Corporation) The structure of the compound was determined by mass spectrometry (LC: Agilent 1100, MASS: Agilent The molecular ion peak was measured using a LC / MSD (manufactured by ent). In the examples, the value of this molecular ion peak is indicated by "MASS."

[0240] Example 1: Synthesis of salt represented by formula (I-8) JPEG2026027464000142.jpg77165 1.43 parts of a salt represented by formula (I-8-a), 0.9 parts of a compound represented by formula (I-8-b) 6 parts of the hydroxybenzoate and 10 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. To the mixture, 0.40 parts of potassium carbonate was added, and the mixture was stirred at 23°C for 30 minutes. C. for 20 hours to obtain a mixture containing a salt represented by formula (I-8-c). The resulting mixture was cooled to 23°C, and then 11 parts of a 5% aqueous oxalic acid solution was added and the mixture was stirred for 3 minutes at 23°C. After stirring for 10 minutes, 2.63 parts of the salt represented by formula (I-8-d) was added, and the mixture was stirred at 23°C for 7 hours. To the resulting reaction mixture, 30 parts of chloroform and 30 parts of ion-exchanged water were added, and the resulting mixture was stirred for 2 hours. After stirring at 3°C ​​for 30 minutes, the organic layer was separated and collected. 30 parts of exchanged water was added, and the mixture was stirred at 23°C for 30 minutes, after which the organic layer was separated and taken out. The water washing procedure was repeated seven times. The obtained organic layer was concentrated, and then the concentrated residue was treated with acetonitrile. 1 part of methyl alcohol and 30 parts of tert-butyl methyl ether were added, and the mixture was stirred at 23°C for 30 minutes. After that, the supernatant was removed and the mixture was concentrated to obtain 0.96 parts of the salt represented by formula (I-8). Ta. MASS(ESI(+)Spectrum):M + 495.0 MASS(ESI(-)Spectrum):M - 517.1

[0241] Example 2: Synthesis of salt represented by formula (I-312) JPEG2026027464000143.jpg77163 1.43 parts of a salt represented by formula (I-8-a), 1 part of a compound represented by formula (I-312-b) 0.54 parts of dimethylformamide and 10 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. To the mixture, 0.40 parts of potassium carbonate was added, and the mixture was stirred at 23°C for 30 minutes. By stirring at 90°C for 20 hours, a mixture containing a salt represented by formula (I-312-c) The resulting mixture was cooled to 23°C, and then 11 parts of a 5% aqueous oxalic acid solution was added. After stirring at 3°C ​​for 30 minutes, 2.63 parts of the salt represented by formula (I-8-d) was added, and the mixture was stirred at 23°C. The mixture was stirred at rt for 7 hours. To the resulting reaction mixture, 30 parts of chloroform and 30 parts of ion-exchanged water were added. After stirring at 23°C for 30 minutes, the organic layer was separated and extracted. 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes, and then the organic layer was separated. This water washing procedure was repeated seven times. The resulting organic layer was concentrated, and the concentrated mixture was passed through a column ( Silica gel 60N (spherical, neutral) 100-210 μm; Kanto Chemical Co., Ltd. Developing solvent: By separating the compound using a mixture of ethanol and chloroform (1 / 1), the compound represented by formula (I-312) was obtained. 0.56 parts of the salt were obtained. MASS(ESI(+)Spectrum):M+ 636.9 MASS(ESI(-)Spectrum):M - 517.1

[0242] Example 3: Synthesis of salt represented by formula (I-320) JPEG2026027464000144.jpg77163 1.43 parts of a salt represented by formula (I-8-a), 1 part of a compound represented by formula (I-312-b) 0.54 parts of dimethylformamide and 10 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. To the mixture, 0.40 parts of potassium carbonate was added, and the mixture was stirred at 23°C for 30 minutes. By stirring at 90°C for 20 hours, a mixture containing a salt represented by formula (I-312-c) The resulting mixture was cooled to 23°C, and then 11 parts of a 5% aqueous oxalic acid solution was added. After stirring at 3°C ​​for 30 minutes, 2.34 parts of the salt represented by formula (I-320-d) was added, and The mixture was stirred for 7 hours at 3° C. The resulting reaction mixture was added with 30 parts of chloroform and 30 parts of ion-exchanged water. The mixture was stirred at 23°C for 30 minutes, and then the organic layer was separated. To the layer, 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes, and then the organic layer was separated. This water washing procedure was repeated seven times. The obtained organic layer was concentrated, and the concentrated mixture was then extracted with column extract. Silica gel 60N (spherical, neutral) 100-210 μm; Kanto Chemical Co., Ltd., eluent : methanol / chloroform = 1 / 1) to obtain the compound represented by formula (I-320) 0.41 parts of a salt represented by the formula: MASS(ESI(+)Spectrum):M + 636.9 MASS(ESI(-)Spectrum):M - 467.1

[0243] Example 4: Synthesis of salt represented by formula (I-350) JPEG2026027464000145.jpg74163 1.43 parts of a salt represented by formula (I-8-a), 1 part of a compound represented by formula (I-350-b) 0.54 parts of dimethylformamide and 10 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. To the mixture, 0.40 parts of potassium carbonate was added, and the mixture was stirred at 23°C for 30 minutes. By stirring at 90°C for 20 hours, a mixture containing a salt represented by formula (I-350-c) The resulting mixture was cooled to 23°C, and then 11 parts of a 5% aqueous oxalic acid solution was added. After stirring at 3°C ​​for 30 minutes, 2.63 parts of the salt represented by formula (I-8-d) was added, and the mixture was stirred at 23°C. The mixture was stirred at rt for 7 hours. To the resulting reaction mixture, 30 parts of chloroform and 30 parts of ion-exchanged water were added. After stirring at 23°C for 30 minutes, the organic layer was separated and extracted. 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes, and then the organic layer was separated. This water washing procedure was repeated seven times. The resulting organic layer was concentrated, and the concentrated mixture was passed through a column ( Silica gel 60N (spherical, neutral) 100-210 μm; Kanto Chemical Co., Ltd. Developing solvent: By separating the compound using a mixture of ethanol and chloroform (1 / 1), the compound represented by formula (I-350) was obtained. 0.42 parts of the salt were obtained. MASS(ESI(+)Spectrum):M + 636.9 MASS(ESI(-)Spectrum):M - 517.1

[0244] Example 5: Synthesis of salt represented by formula (I-358) JPEG2026027464000146.jpg79163 1.43 parts of a salt represented by formula (I-8-a), 1 part of a compound represented by formula (I-350-b) 0.54 parts of dimethylformamide and 10 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. To the mixture, 0.40 parts of potassium carbonate was added, and the mixture was stirred at 23°C for 30 minutes. By stirring at 90°C for 20 hours, a mixture containing a salt represented by formula (I-350-c) The resulting mixture was cooled to 23°C, and then 11 parts of a 5% aqueous oxalic acid solution was added. After stirring at 3°C ​​for 30 minutes, 2.34 parts of the salt represented by formula (I-320-d) was added, and The mixture was stirred for 7 hours at 3° C. The resulting reaction mixture was added with 30 parts of chloroform and 30 parts of ion-exchanged water. The mixture was stirred at 23°C for 30 minutes, and then the organic layer was separated. To the layer, 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes, and then the organic layer was separated. This water washing procedure was repeated seven times. The obtained organic layer was concentrated, and the concentrated mixture was then extracted with column extract. Silica gel 60N (spherical, neutral) 100-210 μm; Kanto Chemical Co., Ltd., eluent : methanol / chloroform = 1 / 1) to obtain the compound represented by formula (I-358) 0.30 parts of a salt represented by the formula: MASS(ESI(+)Spectrum):M + 636.9 MASS(ESI(-)Spectrum):M - 467.1

[0245] Example 6: Synthesis of salt represented by formula (I-388) JPEG2026027464000147.jpg77163 1.43 parts of a salt represented by formula (I-8-a), 1 part of a compound represented by formula (I-388-b) 0.60 parts of dimethylformamide and 10 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. To the mixture, 0.40 parts of potassium carbonate was added, and the mixture was stirred at 23°C for 30 minutes. By stirring at 90°C for 20 hours, a mixture containing a salt represented by formula (I-388-c) The resulting mixture was cooled to 23°C, and then 11 parts of a 5% aqueous oxalic acid solution was added. After stirring at 3°C ​​for 30 minutes, 2.63 parts of the salt represented by formula (I-8-d) was added, and the mixture was stirred at 23°C. The mixture was stirred at rt for 7 hours. To the resulting reaction mixture, 30 parts of chloroform and 30 parts of ion-exchanged water were added. After stirring at 23°C for 30 minutes, the organic layer was separated and extracted. 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes, and then the organic layer was separated. This water washing procedure was repeated seven times. The resulting organic layer was concentrated, and the concentrated mixture was passed through a column ( Silica gel 60N (spherical, neutral) 100-210 μm; Kanto Chemical Co., Ltd. Developing solvent: By separating the compound using a mixture of ethanol and chloroform (1 / 1), the compound represented by formula (I-388) was obtained. 0.68 parts of the salt were obtained. MASS(ESI(+)Spectrum):M + 650.9 MASS(ESI(-)Spectrum):M - 517.1

[0246] Example 7: Synthesis of salt represented by formula (I-396) JPEG2026027464000148.jpg77163 1.43 parts of a salt represented by formula (I-8-a), 1 part of a compound represented by formula (I-388-b) 0.60 parts of dimethylformamide and 10 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. To the mixture, 0.40 parts of potassium carbonate was added, and the mixture was stirred at 23°C for 30 minutes. By stirring at 90°C for 20 hours, a mixture containing a salt represented by formula (I-388-c) The resulting mixture was cooled to 23°C, and then 11 parts of a 5% aqueous oxalic acid solution was added. After stirring at 3°C ​​for 30 minutes, 2.34 parts of the salt represented by formula (I-320-d) was added, and The mixture was stirred for 7 hours at 3° C. The resulting reaction mixture was added with 30 parts of chloroform and 30 parts of ion-exchanged water. The mixture was stirred at 23°C for 30 minutes, and then the organic layer was separated. To the layer, 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes, and then the organic layer was separated. This water washing procedure was repeated seven times. The obtained organic layer was concentrated, and the concentrated mixture was then extracted with column extract. Silica gel 60N (spherical, neutral) 100-210 μm; Kanto Chemical Co., Ltd., eluent : methanol / chloroform = 1 / 1) to obtain the compound represented by formula (I-396) 0.66 parts of a salt represented by the formula: MASS(ESI(+)Spectrum):M + 650.9 MASS(ESI(-)Spectrum):M - 467.1

[0247] Example 8: Synthesis of salt represented by formula (I-920) JPEG2026027464000149.jpg77163 1.43 parts of a salt represented by formula (I-8-a), 1 part of a compound represented by formula (I-920-b) 0.99 parts of the hydroxybenzoate and 10 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. To the mixture, 0.40 parts of potassium carbonate was added, and the mixture was stirred at 23°C for 30 minutes. By stirring at 90°C for 20 hours, a mixture containing a salt represented by formula (I-920-c) The resulting mixture was cooled to 23°C, and then 11 parts of a 5% aqueous oxalic acid solution was added. After stirring at 3°C ​​for 30 minutes, 2.63 parts of the salt represented by formula (I-8-d) was added, and the mixture was stirred at 23°C. The mixture was stirred at rt for 7 hours. To the resulting reaction mixture, 30 parts of chloroform and 30 parts of ion-exchanged water were added. After stirring at 23°C for 30 minutes, the organic layer was separated and extracted. 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes, and then the organic layer was separated. This water washing procedure was repeated seven times. The resulting organic layer was concentrated, and the concentrated mixture was passed through a column ( Silica gel 60N (spherical, neutral) 100-210 μm; Kanto Chemical Co., Ltd. Developing solvent: By separating the compound using a mixture of ethanol and chloroform (1 / 1), the compound represented by formula (I-920) was obtained. 0.67 parts of the salt were obtained. MASS(ESI(+)Spectrum):M + 746.8 MASS(ESI(-)Spectrum):M - 517.1

[0248] Example 9: Synthesis of salt represented by formula (I-958) JPEG2026027464000150.jpg79163 1.43 parts of a salt represented by formula (I-8-a), 1 part of a compound represented by formula (I-958-b) 0.99 parts of the hydroxybenzoate and 10 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. To the mixture, 0.40 parts of potassium carbonate was added, and the mixture was stirred at 23°C for 30 minutes. By stirring at 90°C for 20 hours, a mixture containing a salt represented by formula (I-958-c) The resulting mixture was cooled to 23°C, and then 11 parts of a 5% aqueous oxalic acid solution was added. After stirring at 3°C ​​for 30 minutes, 2.63 parts of the salt represented by formula (I-8-d) was added, and the mixture was stirred at 23°C. The mixture was stirred at rt for 7 hours. To the resulting reaction mixture, 30 parts of chloroform and 30 parts of ion-exchanged water were added. After stirring at 23°C for 30 minutes, the organic layer was separated and extracted. 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes, and then the organic layer was separated. This water washing procedure was repeated seven times. The resulting organic layer was concentrated, and the concentrated mixture was passed through a column ( Silica gel 60N (spherical, neutral) 100-210 μm; Kanto Chemical Co., Ltd. Developing solvent: By separating the compound using a mixture of ethanol and chloroform (1 / 1), the compound represented by formula (I-958) was obtained. 0.62 parts of the salt were obtained. MASS(ESI(+)Spectrum):M + 746.8 MASS(ESI(-)Spectrum):M - 517.1

[0249] Example 10: Synthesis of salt represented by formula (I-16) JPEG2026027464000151.jpg74165 1.43 parts of a salt represented by formula (I-8-a), 0.9 parts of a compound represented by formula (I-8-b) 6 parts of the hydroxybenzoate and 10 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. To the mixture, 0.40 parts of potassium carbonate was added, and the mixture was stirred at 23°C for 30 minutes. C. for 20 hours to obtain a mixture containing a salt represented by formula (I-8-c). The resulting mixture was cooled to 23°C, and then 11 parts of a 5% aqueous oxalic acid solution was added and the mixture was stirred for 3 minutes at 23°C. After stirring for 10 minutes, 2.34 parts of the salt represented by the formula (I-320-d) was added, and the mixture was stirred at 23°C for 7 minutes. To the resulting reaction mixture, 30 parts of chloroform and 30 parts of ion-exchanged water were added. After stirring at 23°C for 30 minutes, the organic layer was separated and collected. 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes, followed by separation to remove the organic layer. This water washing procedure was repeated seven times. The obtained organic layer was concentrated, and then the concentrated residue was diluted with acetonitrile. Add 1 part of tolyl and 30 parts of tert-butyl methyl ether, and stir at 23°C for 30 minutes. After the reaction, the supernatant was removed and the mixture was concentrated to give 1.04% of the salt represented by formula (I-16). won the division. MASS(ESI(+)Spectrum):M + 495.0 MASS(ESI(-)Spectrum):M - 467.1

[0250] Example 11: Synthesis of salt represented by formula (I-22) JPEG2026027464000152.jpg72161 1.43 parts of a salt represented by formula (I-8-a), 0.9 parts of a compound represented by formula (I-8-b) 6 parts of the hydroxybenzoate and 10 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. To the mixture, 0.40 parts of potassium carbonate was added, and the mixture was stirred at 23°C for 30 minutes. C. for 20 hours to obtain a mixture containing a salt represented by formula (I-8-c). The resulting mixture was cooled to 23°C, and then 11 parts of a 5% aqueous oxalic acid solution was added and the mixture was stirred for 3 minutes at 23°C. After stirring for 10 minutes, 2.40 parts of the salt represented by formula (I-22-d) was added, and the mixture was stirred at 23°C for 7 hours. To the resulting reaction mixture, 30 parts of chloroform and 30 parts of ion-exchanged water were added, and the mixture was stirred for 1 hour. After stirring at 23°C for 30 minutes, the organic layer was separated and extracted. 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes, and then the organic layer was separated. This water washing procedure was repeated seven times. The obtained organic layer was concentrated, and then acetonitrile was added to the concentrated residue. 1 part of methyl alcohol and 30 parts of tert-butyl methyl ether were added, and the mixture was stirred at 23°C for 30 minutes. After that, the supernatant was removed and the mixture was concentrated to obtain 1.12 parts of the salt represented by formula (I-22). obtained. MASS(ESI(+)Spectrum):M + 495.0 MASS(ESI(-)Spectrum):M - 481.1

[0251] Example 12: Synthesis of salt represented by formula (I-326) JPEG2026027464000153.jpg74163 1.43 parts of a salt represented by formula (I-8-a), 1 part of a compound represented by formula (I-312-b) 0.54 parts of dimethylformamide and 10 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. To the mixture, 0.40 parts of potassium carbonate was added, and the mixture was stirred at 23°C for 30 minutes. By stirring at 90°C for 20 hours, a mixture containing a salt represented by formula (I-312-c) The resulting mixture was cooled to 23°C, and then 11 parts of a 5% aqueous oxalic acid solution was added. After stirring at 3°C ​​for 30 minutes, 2.40 parts of the salt represented by formula (I-22-d) was added, and 23 The mixture was stirred at 0°C for 7 hours. 30 parts of chloroform and 30 parts of ion-exchanged water were added to the reaction mixture. After adding the mixture and stirring at 23°C for 30 minutes, the organic layer was separated and collected. 30 parts of ion-exchanged water was added to the mixture, and the mixture was stirred at 23°C for 30 minutes, and then the organic layer was separated. This water washing procedure was repeated seven times. The resulting organic layer was concentrated, and the concentrated mixture was then passed through a column. (Silica gel 60N (spherical, neutral) 100-210 μm; manufactured by Kanto Chemical Co., Ltd., Developing solvent: By separating the compound using methanol / chloroform (1 / 1), the compound represented by formula (I-326) was obtained. 0.45 parts of the salt represented by the formula (I) were obtained. MASS(ESI(+)Spectrum):M + 636.9 MASS(ESI(-)Spectrum):M - 481.1

[0252] Example 13: Synthesis of salt represented by formula (I-402) JPEG2026027464000154.jpg77163 1.43 parts of a salt represented by formula (I-8-a), 1 part of a compound represented by formula (I-388-b) 0.60 parts of dimethylformamide and 10 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. To the mixture, 0.40 parts of potassium carbonate was added, and the mixture was stirred at 23°C for 30 minutes. By stirring at 90°C for 20 hours, a mixture containing a salt represented by formula (I-388-c) The resulting mixture was cooled to 23°C, and then 11 parts of a 5% aqueous oxalic acid solution was added. After stirring at 3°C ​​for 30 minutes, 2.40 parts of the salt represented by formula (I-22-d) was added, and 23 The mixture was stirred at 0°C for 7 hours. 30 parts of chloroform and 30 parts of ion-exchanged water were added to the reaction mixture. After adding the mixture and stirring at 23°C for 30 minutes, the organic layer was separated and collected. 30 parts of ion-exchanged water was added to the mixture, and the mixture was stirred at 23°C for 30 minutes, and then the organic layer was separated. This water washing procedure was repeated seven times. The resulting organic layer was concentrated, and the concentrated mixture was then passed through a column. (Silica gel 60N (spherical, neutral) 100-210 μm; manufactured by Kanto Chemical Co., Ltd., Developing solvent: By separating the compound using methanol / chloroform (1 / 1), the compound represented by formula (I-402) was obtained. 0.79 parts of the salt represented by the formula (I) were obtained. MASS(ESI(+)Spectrum):M + 650.9 MASS(ESI(-)Spectrum):M - 481.1

[0253] Example 14: Synthesis of salt represented by formula (I-1580) JPEG2026027464000155.jpg99158 1.51 parts of a salt represented by formula (I-1580-a), a compound represented by formula (I-312-b) 3.08 parts of the mixture and 20 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. To the resulting mixture, 0.80 parts of potassium carbonate was added, and the mixture was stirred at 23°C for 30 minutes. Furthermore, by stirring at 90°C for 20 hours, a solution containing a salt represented by formula (I-1580-c) was obtained. The resulting mixture was cooled to 23°C, and then 11 parts of a 5% aqueous oxalic acid solution was added. After stirring at 23°C for 30 minutes, 2.40 parts of the salt represented by formula (I-22-d) was added. The mixture was stirred at 23° C. for 7 hours. The resulting reaction mixture was added with 30 parts of chloroform and ion-exchanged water. After stirring at 23°C for 30 minutes, the organic layer was separated and extracted. To the organic layer, 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes. The resulting organic layer was concentrated to give a concentrated mixture. The column (silica gel 60N (spherical, neutral) 100-210 μm; Kanto Chemical Co., Ltd.) The compound of formula (I-1) was obtained by fractionation using a solvent (methanol / chloroform = 1 / 1). 0.82 parts of the salt represented by formula (580) were obtained. MASS(ESI(+)Spectrum):M + 1010.8 MASS(ESI(-)Spectrum):M - 481.1

[0254] Example 15: Synthesis of salt represented by formula (I-1656) JPEG2026027464000156.jpg115161 1.59 parts of a salt represented by formula (I-1656-a), a compound represented by formula (I-312-b) 4.62 parts of the mixture and 20 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. To the resulting mixture, 1.20 parts of potassium carbonate was added, and the mixture was stirred at 23°C for 30 minutes. Furthermore, by stirring at 90°C for 20 hours, a salt containing the formula (I-1656-c) was obtained. The resulting mixture was cooled to 23°C, and then 11 parts of a 5% aqueous oxalic acid solution was added. After stirring at 23°C for 30 minutes, 2.40 parts of the salt represented by formula (I-22-d) was added. The mixture was stirred at 23° C. for 7 hours. The resulting reaction mixture was added with 30 parts of chloroform and ion-exchanged water. After stirring at 23°C for 30 minutes, the organic layer was separated and extracted. To the organic layer, 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes. The resulting organic layer was concentrated to give a concentrated mixture. The column (silica gel 60N (spherical, neutral) 100-210 μm; Kanto Chemical Co., Ltd.) The compound of formula (I-1) was obtained by fractionation using a solvent (methanol / chloroform = 1 / 1). 0.76 parts of a salt represented by formula (656) was obtained. MASS(ESI(+)Spectrum):M + 1384.6 MASS(ESI(-)Spectrum):M - 481.1

[0255] Synthesis Example 1: Synthesis of a salt represented by formula (IX-5) JPEG2026027464000157.jpg79161 2.25 parts of the compound represented by formula (IX-5-b) and 30 parts of chloroform were mixed, and 2 The mixture was stirred at 3° C. for 30 minutes. 0.73 parts of carbonyldiimidazole was added to the resulting mixture. The mixture was then stirred at 50° C. for 2 hours. The mixture was 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. The organic layer was separated and the organic layer was extracted. 15 parts of ion-exchanged water was added to the obtained organic layer and the mixture was stirred at 23°C. After stirring for 30 minutes, the organic layer was separated and extracted. ) was added to the reaction mixture, and the mixture was stirred at 23°C for 2 hours. 30 parts of chloroform and 30 parts of ion-exchanged water were added, and the mixture was stirred at 23°C for 30 minutes, followed by separation. The organic layer was collected by adding 30 parts of ion-exchanged water, and the mixture was stirred at 23°C for 3 hours. After stirring for 10 minutes, the organic layer was separated and washed with water 7 times. The organic layer was concentrated, and then 30 parts of tert-butyl methyl ether was added to the concentrated residue. After stirring at 23°C for 30 minutes, the supernatant was removed and the mixture was concentrated to give the compound of formula (IX-5 2.18 parts of a salt represented by the formula (II) were obtained. MASS(ESI(+)Spectrum):M + 760.8 MASS(ESI(-)Spectrum):M - 517.1

[0256] Synthesis Example 2: Synthesis of a salt represented by formula (IX-6) JPEG2026027464000158.jpg721581.43 parts of a salt represented by formula (I-8-a), 2 parts of a compound represented by formula (IX-6-b). 11 parts of the hydroxybenzoate and 10 parts of dimethylformamide were mixed and stirred at 23°C for 30 minutes. To the mixture, 0.40 parts of potassium carbonate was added, and the mixture was stirred at 23°C for 30 minutes. After stirring at 0°C for 20 hours, a mixture containing a salt represented by formula (IX-6-c) was obtained. The resulting mixture was cooled to 23°C, and then 11 parts of a 5% aqueous oxalic acid solution was added and the mixture was heated to 23°C. After stirring for 30 minutes at 40°C, 2.63 parts of a salt represented by formula (I-8-d) was added, and the mixture was stirred at 23°C for 7 To the resulting reaction mixture, 30 parts of chloroform and 30 parts of ion-exchanged water were added. After stirring at 23°C for 30 minutes, the organic layer was separated and collected. 30 parts of ion-exchanged water was added, and the mixture was stirred at 23°C for 30 minutes, followed by separation to remove the organic layer. This water washing procedure was repeated seven times. The resulting organic layer was concentrated, and the concentrated mixture was passed through a column (silica Spherical gel 60N (neutral) 100-210 μm; Kanto Chemical Co., Ltd., eluent: methyl alcohol By separating the compound using a mixture of ethanol and chloroform (1 / 1), the compound represented by formula (IX-6) was obtained. 0.44 parts of salt was obtained. MASS(ESI(+)Spectrum):M + 776.8 MASS(ESI(-)Spectrum):M - 517.1

[0257] Resin synthesis The compounds (monomers) used in the synthesis of resin (A) are shown below. are referred to as "monomer (a1-1-3)" etc. according to their formula numbers. JPEG2026027464000159.jpg38165

[0258] Synthesis Example 3 [Synthesis of Resin A1] As the monomers, the monomer (a1-4-2), the monomer (a1-1-3) and the monomer (a1-2-6) was used, and the molar ratio [monomer (a1-4-2):monomer (a1-1 -3):monomer (a1-2-6) in a ratio of 38:24:38, Furthermore, this monomer mixture was mixed with 1.5 times by mass of methyl methyl ester based on the total mass of all monomers. Isobutyl ketone was mixed in the resulting mixture, and azobisisobutyronite was added as an initiator. The amount of methyl acrylate was 7 mol % based on the total number of moles of all monomers. Polymerization was carried out by heating at 40°C for about 5 hours. After that, the polymerization reaction solution was 2.0 times the mass of p-toluenesulfonic acid aqueous solution (2.5 wt%) was added to the After stirring for 1 hour, the mixture was separated. The obtained organic layer was poured into a large amount of n-heptane to precipitate the resin. After filtration and recovery, the weight-average molecular weight was found to be approximately 5.3 x 10 3 Resin A1 (copolymer Resin A1 was obtained in a yield of 78%. This resin A1 has the following structural units. JPEG2026027464000160.jpg28125

[0259] Synthesis Example 4 [Synthesis of Resin A2] As the monomers, the monomer (a1-4-2) and the monomer (a1-2-6) were used. The molar ratio of monomer (a1-4-2):monomer (a1-2-6) was 38:62. Further, to this monomer mixture, 1.5 times by mass of methyl isobutyl ketone was mixed with the resulting mixture. Azobisisobutyronitrile was added at 7 mol% relative to the total moles of all monomers. The mixture was then heated at 85°C for approximately 5 hours to carry out polymerization. , 2.0 times by mass of p-toluenesulfonic acid aqueous solution (2. After stirring for 6 hours, the resulting organic layer was separated. The resin was poured into a filter to precipitate, and then filtered and collected to obtain a resin with a weight-average molecular weight of approximately 5.4 × 10 3 Resin A2 (copolymer) was obtained in a yield of 89%. This resin A2 has the following structural units: It is something that we possess. JPEG2026027464000161.jpg2887

[0260] Synthesis Example 5 [Synthesis of Resin A3] As the monomers, monomer (a1-1-3), monomer (a1-2-6), monomer ( a2-1-3), monomer (a3-4-2) and monomer (a1-4-2), Molar ratio [monomer (a1-1-3):monomer (a1-2-6):monomer (a2-1- 3): Monomer (a3-4-2): Monomer (a1-4-2) Mix them in a ratio of 5:27, and then add the total amount of all the monomers to this monomer mixture. Methyl isobutyl ketone was added in an amount of 1.5 times by mass relative to the mass of the resulting mixture. Azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were used as initiators. The total amount of monomers was 1.2 mol % and 3.6 mol %. The mixture was heated at 73°C for about 5 hours. Then, 2% by weight of the total weight of all the monomers was added to the polymerization reaction mixture. 0.0 times the mass of an aqueous solution of p-toluenesulfonic acid (2.5 wt%) was added and stirred for 12 hours. The recovered organic layer was poured into a large amount of n-heptane to precipitate the resin, which was then filtered. By collecting the product, the weight-average molecular weight was reduced to approximately 5.3 × 10 3 Resin A3 was obtained in a yield of 63%. This resin A3 has the following structural units. JPEG2026027464000162.jpg38155

[0261] Synthesis Example 6 [Synthesis of Resin A4] As the monomers, monomer (a1-1-3), monomer (a1-2-6), monomer ( a2-1-3), monomer (a3-4-2) and monomer (a1-4-13), The molar ratio of monomer (a1-1-3):monomer (a1-2-6):monomer (a2-1 -3): Monomer (a3-4-2): Monomer (a1-4-13) The monomer mixture was mixed in a ratio of 15:27. Methyl isobutyl ketone was added in an amount 1.5 times by mass relative to the total mass of the mixture. In addition, azobisisobutyronitrile and azobis(2,4-dimethylvaleronitrile) were used as initiators. Tolyl) were added in amounts of 1.2 mol% and 3.6 mol% based on the total amount of monomers, respectively. The mixture was heated at 73°C for about 5 hours. After that, the polymerization reaction mixture was 2.0 times the mass of the p-toluenesulfonic acid aqueous solution (2.5 wt%) was added, and the mixture was stirred for 12 hours. The collected organic layer was poured into a large amount of n-heptane to precipitate the resin, and then filtered. By filtering and recovering the product, the weight average molecular weight was reduced to approximately 5.1 x 10 3 Resin A4 was obtained in a yield of 61 %. This resin A4 has the following structural units. JPEG2026027464000163.jpg38155

[0262] Synthesis Example 7 [Synthesis of Resin A5] As the monomers, monomer (a1-2-6), monomer (a2-1-3), monomer ( a3-4-2 and monomer (a1-4-19) were used, and the molar ratio [monomer (a1- 2-6): Monomer (a2-1-3): Monomer (a3-4-2): Monomer (a1-4 -19)) were mixed in a ratio of 53:3:12:32, and then this monomer The mixture was mixed with 1.5 times the mass of methyl isobutyl ketone relative to the total mass of all monomers. The resulting mixture was mixed with azobisisobutyronitrile and azobis(2 ,4-dimethylvaleronitrile) were added at 1.2 mol% and 3. 6 mol % of ethylenediaminetetraacetic acid was added, and the mixture was heated at 73°C for about 5 hours. A p-toluenesulfonic acid aqueous solution (2.5 wt%) was added at 2.0 times the total mass of the mers. %) was added, and the mixture was stirred for 12 hours, followed by separation. The recovered organic layer was diluted with a large amount of n-heptane The resin was precipitated by pouring it into a flask, and then filtered and collected to obtain a resin with a weight-average molecular weight of approximately 5.5 × 10 3 Resin A5 was obtained in a yield of 74%. This resin A5 has the following structural units: do. JPEG2026027464000164.jpg38127

[0263] Synthesis Example 8 [Synthesis of Resin A6] As the monomers, monomer (a1-2-6), monomer (a2-1-3), monomer ( a3-4-2 and monomer (a1-4-20) were used, and the molar ratio [monomer (a1- 2-6): Monomer (a2-1-3): Monomer (a3-4-2): Monomer (a1-4 -20) in a ratio of 53:3:12:32, and then this monomer The mixture was mixed with 1.5 times the mass of methyl isobutyl ketone relative to the total mass of all monomers. The resulting mixture was mixed with azobisisobutyronitrile and azobis(2 ,4-dimethylvaleronitrile) were added at 1.2 mol% and 3. 6 mol % of ethylenediaminetetraacetic acid was added, and the mixture was heated at 73°C for about 5 hours. A p-toluenesulfonic acid aqueous solution (2.5 wt%) was added at 2.0 times the total mass of the mers. %) was added, and the mixture was stirred for 12 hours, followed by separation. The recovered organic layer was diluted with a large amount of n-heptane The resin was precipitated by pouring it into a flask, and then filtered and collected to obtain a resin with a weight-average molecular weight of approximately 5.2 × 10 3 Resin A6 was obtained in a yield of 66%. This resin A6 has the following structural units: do. JPEG2026027464000165.jpg38127

[0264] Synthesis Example 9 [Synthesis of Resin A7] As the monomers, monomer (a1-2-6), monomer (a2-1-3), monomer ( a3-4-2 and monomer (a1-4-13) were used, and the molar ratio [monomer (a1- 2-6): Monomer (a2-1-3): Monomer (a3-4-2): Monomer (a1-4 -13)) were mixed in a ratio of 53:3:12:32, and then this monomer The mixture was mixed with 1.5 times the mass of methyl isobutyl ketone relative to the total mass of all monomers. The resulting mixture was mixed with azobisisobutyronitrile and azobis(2 ,4-dimethylvaleronitrile) were added at 1.2 mol% and 3. 6 mol % of ethylenediaminetetraacetic acid was added, and the mixture was heated at 73°C for about 5 hours. A p-toluenesulfonic acid aqueous solution (2.5 wt%) was added at 2.0 times the total mass of the monomers. The organic layer was added to the mixture, stirred for 12 hours, and then separated. The resin was precipitated by pouring it in, and then filtered and collected to obtain a resin with a weight-average molecular weight of approximately 5.1 × 10 3 in A resin A7 was obtained in a yield of 79%. This resin A7 has the following structural units: . JPEG2026027464000166.jpg38127

[0265] <Preparation of Resist Composition> As shown in Table 2, the following components were mixed, and the resulting mixture was passed through a fluorine-containing filter with a pore size of 0.2 μm. The mixture was filtered through a resin filter to prepare a resist composition. [Table 2] TIFF2026027464000168.tif73168

[0266] <Resin> A1~A7: Resin A1~Resin A7 <Salt (I)> I-8: Salt represented by formula (I-8) I-16: Salt represented by formula (I-16) I-22: A salt represented by formula (I-22) I-312: A salt represented by formula (I-312) I-320: A salt represented by the formula (I-320) I-326: A salt represented by the formula (I-326) I-350: A salt represented by the formula (I-350) I-358: A salt represented by the formula (I-358) I-388: A salt represented by the formula (I-388) I-396: A salt represented by the formula (I-396) I-402: A salt represented by formula (I-402) I-920: A salt represented by the formula (I-920) I-958: A salt represented by the formula (I-958) I-1580: A salt represented by the formula (I-1580) I-1656: A salt represented by the formula (I-1656) <Acid generator> IX-1 IX-2 IX-3 IX-4 JPEG2026027464000169.jpg64161IX-5: Salt represented by formula (IX-5) IX-6: A salt represented by formula (IX-6) <Quencher (C)> C1: Synthesized by the method described in JP 2011-39502 A JPEG2026027464000170.jpg3646<solvent> Propylene glycol monomethyl ether acetate 400 parts Propylene glycol monomethyl ether 100 parts γ-butyrolactone 5 parts

[0267] (Electron beam exposure evaluation of resist composition: alkaline development) A 6-inch silicon wafer is heated on a direct hot plate with hexamethyldisilazane. The silicon wafer was treated at 90°C for 60 seconds using a resist composition. The layer was spin-coated to a thickness of 0.04 μm. The substrate was prebaked on the sheet for 60 seconds at the temperature shown in the "PB" column of Table 2 to form a composition layer. The composition layer formed on the wafer was subjected to an electron beam lithography machine (HL-800D manufactured by Hitachi, Ltd.). 50 keV] and gradually change the exposure dose to create a line and space pattern ( Direct writing was performed using a 60 nm pitch and 30 nm line width. After exposure, the film was post-exposed on a hot plate for 60 seconds at the temperature shown in the "PEB" column of Table 2. The developer was 2.38% by weight of tetramethylammonium hydroxide. A resist pattern was obtained by puddle development using an aqueous solution of methyl hydroxybenzoate for 60 seconds. The resulting resist pattern (line and space pattern) was observed with a scanning electron microscope. Assuming that the line width and space width of a line and space pattern with a pitch of 60 nm are 1: The exposure amount at which the sensitivity reached 1 was defined as the effective sensitivity.

[0268] Line Edge Roughness Evaluation (LER): Sidewall of resist pattern manufactured with effective sensitivity The amplitude of the unevenness of the surface was measured using a scanning electron microscope to determine the line edge roughness. The results are shown in Table 3. [Table 3] Compared with the comparative compositions 1 to 6, the compositions 1 to 10 and 21 to 26 had a lower line edge roughness. (LER) was good.

[0269] (Electron beam exposure evaluation of resist composition: organic solvent development) A 6-inch silicon wafer is heated on a direct hot plate with hexamethyldisilazane. The silicon wafer was treated at 90°C for 60 seconds using a resist composition. The layer was spin-coated to a thickness of 0.04 μm. The substrate was prebaked on the sheet for 60 seconds at the temperature shown in the "PB" column of Table 2 to form a composition layer. The composition layer formed on the wafer was subjected to electron beam lithography using an electron beam lithography machine (ELS-F1 manufactured by Elionix Co., Ltd.). The exposure dose was gradually changed using a 25 125 keV system, and after development, line and square patterns were obtained. Direct writing was performed to create a base pattern (pitch 60 nm / line width 30 nm). After exposure, the film was post-exposed on a hot plate for 60 seconds at the temperature shown in the "PEB" column of Table 2. The composition layer on the silicon wafer was then developed using acetic acid as a developer. Dynamic dispensing using butyl (Tokyo Chemical Industry Co., Ltd.) at 23°C for 20 seconds A resist pattern was obtained by developing the resist film by the method. The resulting resist pattern (line and space pattern) was observed with a scanning electron microscope. Assuming that the line width and space width of a line and space pattern with a pitch of 60 nm are 1: The exposure amount at which the sensitivity reached 1 was defined as the effective sensitivity.

[0270] Line Edge Roughness Evaluation (LER): Sidewall of resist pattern manufactured with effective sensitivity The amplitude of the unevenness of the surface was measured using a scanning electron microscope to determine the line edge roughness. The results are shown in Table 4. [Table 4] Resist patterns of compositions 11 to 20 and 27 to 35 compared to comparative compositions 7 to 12 The fluctuation range of the unevenness on the sidewall surface was small, and the line edge roughness evaluation was good. [Industrial Applicability]

[0271] The resist composition containing the salt of the present invention has good line edge roughness (LER). Since it is possible to obtain a resist pattern suitable for semiconductor microfabrication, it is extremely useful in industry. It is useful.

Claims

1. An acid generator containing a salt represented by formula (I): [In formula (I), R ４ , R ５ , R ６ , R ７ , R ８ and R ９ each independently represents a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, or a hydrocarbon group having 1 to 18 carbon atoms, and the hydrocarbon group may have a substituent, and the —CH 2 - is -O-, -S-, -SO ２ R may be replaced by - or -CO-. ４ At least one of is an iodine atom. A １ is *-L ０１ -X ０１ represents -, and X ０１ is —CO—, —S— or —SO ２ represents -, L ０１ represents an alkanediyl group having 1 to 4 carbon atoms, and * represents R ４ represents the bonding site to the benzene ring to which A ２ and A ３ each independently represents a hydrocarbon group having 2 to 20 carbon atoms, and —CH 2 One of the - is -O-, -CO-, -S- or -SO ２ It may be replaced with -. m1 represents an integer of 1 to 5, and when m1 is 2 or more, 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 more, the groups in the parentheses may be the same or different. m3 represents an integer of 0 to 5, and when m3 is 2 or more, the groups in the parentheses may be the same or different. m4 represents an integer of 1 to 5, 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 5, and when m5 is 2 or more, a plurality of R ５ may be the same or different from each other. m6 represents an integer of 0 to 5, and when m6 is 2 or more, a plurality of R ６ may be the same or different from each other. 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. m9 represents an integer of 0 to 5, and when m9 is 2 or more, a plurality of R ９ may be the same or different from each other. However, 1≦m1+m7≦5, 0≦m2+m8≦5, and 0≦m3+m9≦5. AI － represents an organic anion.

2. A ２ But *-X ０２ -L ０２ - or *-L ０２ -X ０２ - and A ３ But *-X ０３ -L ０３ - or *-L ０３ -X ０３ - (X ０２ and X ０３ each independently represents —O—, —CO—, —S—, or —SO ２ - represents. ０２ and L ０３ each independently represents a hydrocarbon group having 1 to 19 carbon atoms. * represents R ５ or R ６ represents the bonding site to the benzene ring to which 2. The acid generator according to claim 1.

3. X ０２ and X ０３ The acid generator according to claim 2, wherein each of the groups independently represents —O— or —S—.

4. L ０２ and L ０３ and each independently represent an alkanediyl group having 1 to 6 carbon atoms.

5. R ４ , R ５ and R ６ each independently represents 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 (a —CH 2 5. The acid generator according to claim 1, wherein - may be replaced by -O- or -CO-.

6. R ７ , R ８ and R ９ each independently represents 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 (a —CH 2 6. The acid generator according to claim 1, wherein - may be replaced by -O- or -CO-.

7. AI － 7. The acid generator according to claim 1, wherein is a sulfonate anion, a sulfonylimide anion, a sulfonylmethide anion, or a carboxylate anion.

8. AI － 8. The acid generator according to claim 1, wherein: is a sulfonate anion, and the sulfonate anion is an anion represented by formula (IA): [In formula (IA), Q １ and Q ２ each independently represents a hydrogen atom, a fluorine atom, an alkyl group having 1 to 6 carbon atoms, or a perfluoroalkyl group having 1 to 6 carbon atoms. L １ represents a saturated hydrocarbon group having 1 to 24 carbon atoms, and —CH ２ The - may be replaced by -O- or -CO-, and the 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 —CH ２ - is -O-, -S-, -SO ２ - or -CO- may be substituted.]

9. 9. A resist composition comprising the acid generator according to claim 1 and a resin having an acid labile group.

10. 10. The resist composition according to claim 9, wherein the resin having an acid labile group comprises at least one selected from the group consisting of a structural unit represented by formula (a1-0), a structural unit represented by formula (a1-1), and a structural unit represented by formula (a1-2): [In formula (a1-0), formula (a1-1) and formula (a1-2), L a01 , L ａ１ and L ａ２ are each independently —O— or *—O—(CH ２ ) ｋ１ represents —CO—O—, k1 represents an integer of 1 to 7, and * represents the bonding site with —CO—. R a01 , R ａ４ and R ａ５ each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a02 , R a03 and R a04 each independently represents an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group 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 an integer of 0 to 14. n1 represents an integer of 0 to 10. n1′ represents an integer of 0 to 3.]

11. 11. The resist composition according to claim 9, wherein the resin having an acid labile group comprises a structural unit represented by formula (a2-A). [In formula (a2-A), R a50 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom. R a51 represents a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxyalkyl group having 2 to 12 carbon atoms, an alkoxyalkoxy group having 2 to 12 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group, or a methacryloyloxy group. A a50 is a single bond or *-X a51 - (A a52 -X a52 ) nｂ -, * represents -R a50 represents the bonding site with the carbon atom to which it 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 an integer of 0 to 4; When mb is an integer of 2 or more, a plurality of R a51 may be the same or different.]

12. 12. The resist composition according to claim 9, further comprising a salt that generates an acid that is weaker in acidity than the acid generated from the acid generator.

13. (1) a step of applying the resist composition according to any one of claims 9 to 12 onto a substrate; (2) a step of drying the applied composition to form a composition layer; (3) exposing the composition layer to light; (4) a step of heating the composition layer after exposure; and (5) developing the composition layer after heating; A method for producing a resist pattern comprising:

14. A salt represented by formula (I): [In formula (I), R ４ , R ５ , R ６ , R ７ , R ８ and R ９ each independently represents a halogen atom, a haloalkyl group having 1 to 12 carbon atoms, or a hydrocarbon group having 1 to 18 carbon atoms, and the hydrocarbon group may have a substituent, and the —CH 2 - is -O-, -S-, -SO ２ R may be replaced by - or -CO-. ４ At least one of is an iodine atom. A １ is *-L ０１ -X ０１ represents -, and X ０１ is —CO—, —S— or —SO ２ represents -, L ０１ represents an alkanediyl group having 1 to 4 carbon atoms, and * represents R ４ represents the bonding site to the benzene ring to which A ２ and A ３ each independently represents a hydrocarbon group having 2 to 20 carbon atoms, and —CH 2 One of the - is -O-, -CO-, -S- or -SO ２ It may be replaced with -. m1 represents an integer of 1 to 5, and when m1 is 2 or more, 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 more, the groups in the parentheses may be the same or different. m3 represents an integer of 0 to 5, and when m3 is 2 or more, the groups in the parentheses may be the same or different. m4 represents an integer of 1 to 5, 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 5, and when m5 is 2 or more, a plurality of R ５ may be the same or different from each other. m6 represents an integer of 0 to 5, and when m6 is 2 or more, a plurality of R ６ may be the same or different from each other. 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. m9 represents an integer of 0 to 5, and when m9 is 2 or more, a plurality of R ９ may be the same or different from each other. However, 1≦m1+m7≦5, 0≦m2+m8≦5, and 0≦m3+m9≦5. AI － represents an organic anion.

15. A ２ But *-X ０２ -L ０２ - or *-L ０２ -X ０２ - and A ３ But *-X ０３ -L ０３ - or *-L ０３ -X ０３ - (X ０２ and X ０３ each independently represents —O—, —CO—, —S—, or —SO ２ - represents. ０２ and L ０３ each independently represents a hydrocarbon group having 1 to 19 carbon atoms. * represents R ５ or R ６ The salt according to claim 14, wherein:

16. X ０２ and X ０３ The salt according to claim 15, wherein each of the groups independently represents -O- or -S-.

17. L ０２ and L ０３ and each independently represent an alkanediyl group having 1 to 6 carbon atoms.

18. R ４ , R ５ and R ６ each independently represents 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 (a —CH 2 The salt according to any one of claims 14 to 17, wherein - may be replaced by -O- or -CO-.

19. R ７ , R ８ and R ９ each independently represents 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 (a —CH 2 The salt according to any one of claims 14 to 18, wherein - may be replaced by -O- or -CO-.

20. AI － The salt according to any one of claims 14 to 19, wherein is a sulfonate anion, a sulfonylimide anion, a sulfonylmethide anion, or a carboxylate anion.

21. AI － The salt according to any one of claims 14 to 20, wherein the sulfonate anion is an anion represented by formula (IA): [In formula (IA), Q １ and Q ２ each independently represents a hydrogen atom, a fluorine atom, an alkyl group having 1 to 6 carbon atoms, or a perfluoroalkyl group having 1 to 6 carbon atoms. L １ represents a saturated hydrocarbon group having 1 to 24 carbon atoms, and —CH ２ The - may be replaced by -O- or -CO-, and the 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 —CH ２ - is -O-, -S-, -SO ２ - or -CO- may be substituted.]

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