Resist composition and method for producing resist pattern

Abstract

To provide a resist composition capable of producing a resist pattern having good line edge roughness.SOLUTION: The resist composition contains a compound represented by formula (I), a resin having an acid-labile group, and an acid generator. [In the formula, R2 represents * -X1-Ph - L1 - OH. Ph represents a substituted or unsubstituted phenylene; R3 represents a halogen atom, a hydroxy group, a haloalkyl group or an alkyl group, and - CH2 - included in the alkyl group may be replaced by - O - or - CO -. m2 is an integer of 1 to 4, m3 is an integer of 0 to 3, provided that 1 ≤ m2 + m3 ≤ 4, and one or more of L1, R1, R2, and R3 have a halogen atom. ] SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a resist composition and a method for producing a resist pattern using the resist composition. etc. [Background technology]

[0002] Patent Document 1 describes a composition containing a compound of the following structural formula, a resin of the following structural formula, and an acid generator. A resist composition is described. TIFF2026010138000001.tif30121 [Prior art documents] [Patent documents]

[0003] [Patent Document 1] International Publication No. WO2018 / 180049 Summary of the Invention [Problem to be solved by the invention]

[0004] The resist pattern formed from the resist composition has a higher line edge roughness ( The object of the present invention is to provide a resist composition that forms a resist pattern with good LER. do. [Means for solving the problem]

[0005] The present invention includes the following inventions. [1] A composition containing a compound represented by formula (I), a resin having an acid labile group, and an acid generator. A resist composition. TIFF2026010138000002.tif4267 [In formula (I), L 1 represents a single bond or an alkanediyl group having 1 to 6 carbon atoms which may have a substituent. R 1represents a hydrogen atom, a halogen atom, or a haloalkyl group having 1 to 12 carbon atoms. R 2 is *-L 1 -OH or *-X 1 -Ph-L 1 -OH, and * indicates a benzene ring. represents the binding site of X 1 represents a single bond, an alkanediyl group having 1 to 6 carbon atoms, -O-, -S-, -CO-, -S represents -O- or -SO2-. The -CH2- contained in the alkanediyl group having 1 to 6 carbon atoms is , -O-, -S-, -CO-, -SO- or -SO2-. Ph represents a phenylene group which may have a substituent. m2 represents an integer of 1 to 4, and when m2 is 2 or more, a plurality of R 2 are the same as each other They may be the same or different. R 3 is a halogen atom, a hydroxy group, a haloalkyl group having 1 to 12 carbon atoms, or a The alkyl group may be an alkyl group having a molecular weight of 1 to 12, and -CH2- contained in the alkyl group may be -O- or -CO-. may be replaced by . m3 represents an integer of 0 to 3, and when m3 is 2 or more, a plurality of R 3 are the same as each other They may be the same or different, provided that 1≦m2+m3≦4. However, in formula (I), L 1 , R 1 , R 2 and R 3 Any of the following has at least one halogen It has atoms. [2] L 1 alkanediyl having 1 to 4 carbon atoms which may have a single bond or a halogen atom The resist composition according to [1], wherein the compound is a group. [3] In formula (I), m2 is 1, R 2 However, L in the benzene ring 1It is bonded to the meta or para position relative to the bonding position of The resist composition according to [1] or [2]. [4] In formula (I), R 2 is *-L 1

[0023] Any of [1] to [3], wherein the formula represents —OH. gyst composition. [5] In formula (I), R 2 is *-X 1 -Ph-L 1 represents -OH, The Ph is the X 1 - and -L 1 has one or two substituents other than —OH, The substituents are each independently a halogen atom or a fluorinated alkyl group having 1 to 6 carbon atoms. The resist composition according to any one of [1] to [3], wherein the group is a group. [6] X 1 is an alkanediyl group having 1 to 4 carbon atoms (the —C H2- may be replaced by -O-, -S-, -CO-, -SO- or -SO2-. any of [1] to [5], which is -O-, -S-, -CO-, -SO- or -SO2- The resist composition described above. [7] R 3 However, it contains fluorine atoms, iodine atoms, hydroxyl groups, alkyl fluorides with 1 to 3 carbon atoms. a methyl group or an alkyl group having 1 to 3 carbon atoms (wherein -CH2- contained in the alkyl group is -O- or The resist composition according to any one of [1] to [6], wherein —CO— may be replaced by Finished product. [8] The resin having an acid labile group is a structural unit represented by formula (a1-0), a structural unit represented by formula (a1-1 a structural unit represented by the formula (a1-1) and a structural unit represented by the formula (a1-2) The resist composition according to any one of [1] to [7], comprising at least one kind. TIFF2026010138000003.tif46153 [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. [9] The resin having an acid labile group contains a structural unit represented by formula (a2-A) [1] to [8] The resist composition according to any one of [8]. TIFF2026010138000004.tif4652[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.

[10] In formula (a2-A), at least one hydroxy group is A in the benzene ring a50 The resist composition according to [9], wherein the bond is at a meta position relative to the bonding position of

[11] Any one of [1] to

[10] , wherein the acid generator contains a salt represented by formula (B1): A resist composition according to claim 1. TIFF2026010138000005.tif2859[In formula (B1), Q b1 and Q b2 are each independently a hydrogen atom, a fluorine atom, or a perfluoroalkyl group having 1 to 6 carbon atoms. It represents a fluoroalkyl group or an alkyl 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 C3-2 alkyl group 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-. Z + represents an organic cation.

[12] The composition further contains a salt that generates an acid weaker in acidity than the acid generated from the acid generator. The resist composition according to any one of [1] to

[11] .

[13] (1) A resist composition according to any one of [1] to

[12] is applied onto a substrate. process, (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. [Effects of the Invention]

[0006] By using the resist composition of the present invention, it is possible to obtain a resist pattern with good line edge roughness (LER). A resist pattern can be produced. 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 also have the same meaning. In the case where the hydrocarbon can have either a linear structure or a branched structure, either structure may be used. When -CH2- contained in the group is replaced with -O-, -S-, -CO- or -SO2- The same examples apply to each group. "Combined groups" refer to groups that are exemplified above. It means a group in which two or more types of groups are bonded together, and the valence of these groups may be changed appropriately depending on the bonding form. "Derived from" or "derived from" means that the polymerizable C=C bond contained in the molecule is polymerized. When stereoisomers exist, all Includes stereoisomers. In this specification, the term "solid content of the resist composition" refers to the remaining solid content of the resist composition. This refers to the total of all components excluding the solvent (E) described below.

[0008] [Resist Composition] The resist composition of the present invention contains a compound represented by formula (I) (hereinafter referred to as "compound (I)"). a resin having an acid labile group (hereinafter sometimes referred to as "resin (A)"); The acid generator (hereinafter, sometimes referred to as "acid generator (B)") is contained. The "labile group" has a leaving group, and the leaving group is released upon contact with an acid to form a hydrophilic group (e.g., This refers to a group that converts into a structural unit having a hydroxy group or a carboxy group. The resist composition of the present invention may further contain a resin other than the resin (A). The resist composition of the present invention generates an acid that is weaker in acidity than the acid generated from the acid generator. Further containing a quencher such as a salt (hereinafter sometimes referred to as "quencher (C)"). It is preferable that the solvent (E) is contained. Desirable.

[0009] <Compound (I)> The resist composition of the present invention contains compound (I). TIFF2026010138000006.tif4267 [In formula (I), all symbols have the same meanings as defined above.]

[0010] L 1 The alkanediyl group in the formula (I) is 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 6-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 2-methylbutane-1,4-diyl groups. The lucanediyl group preferably has 1 to 4 carbon atoms, and more preferably 1 to 3 carbon atoms. L 1 The substituents that the alkanediyl group may have include a halogen atom, a hydroxy group, , cyano group, carboxy group, alkyl group having 1 to 12 carbon atoms, haloalkyl having 1 to 6 carbon atoms groups, alkoxy groups having 1 to 12 carbon atoms, and groups in which two or more of these groups are combined. It can be obtained. Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. do. Examples of the alkyl group having 1 to 12 carbon atoms include a methyl group, an ethyl group, a propyl group, and an isopropyl group. butyl, isobutyl, tert-butyl, pentyl, hexyl, octyl The number of carbon atoms in the alkyl group is preferably 1 to 9, and more preferably 1 to 9. Preferably, it is 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3 is. The haloalkyl group having 1 to 6 carbon atoms refers to an alkyl group having a halogen atom, and is fluorinated. Examples of the alkyl group include alkyl groups, alkyl chlorides, alkyl bromides, and alkyl iodides. Examples of the alkyl group include a trifluoromethyl group, a difluoromethyl group, and a perfluoroethyl group. group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group, perfluoropropyl group, 2,2,3,3,3-pentafluoropropyl group, perfluoro butyl group, 1,1,2,2,3,3,4,4-octafluorobutyl group, perfluoropentyl group pentyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentyl group, perfluoro Examples of such groups include a hexyl group, a chloromethyl group, a bromomethyl group, and an iodomethyl group. The alkyl group preferably has 1 to 4 carbon atoms, and more preferably 1 to 3 carbon atoms. Examples of the alkoxy group having 1 to 12 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, a bromine group, and a methyl group. hexyloxy, pentyloxy, hexyloxy, octyloxy, 2-ethylhexyl hydroxyl group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group The number of carbon atoms in the alkoxy group is preferably 1 to 9, and more preferably 1 It is preferably 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3. Examples of the group combining two or more of these include an alkoxycarbonyl group having 2 to 13 carbon atoms, a carbon alkylcarbonyl groups having 2 to 13 carbon atoms and alkylcarbonyloxy groups having 2 to 13 carbon atoms, etc. Examples include: Alkoxycarbonyl groups having 2 to 13 carbon atoms, alkylcarbonyl groups having 2 to 13 carbon atoms, and and alkylcarbonyloxy groups having 2 to 13 carbon atoms are the same as the above-mentioned alkyl or alkoxy groups. It represents a group in which a carbonyl group or a carbonyloxy group is bonded to a silyl group. Examples of the alkoxycarbonyl group having 2 to 13 carbon atoms include a methoxycarbonyl group, an ethoxy group, and carbonyl group, butoxycarbonyl group, etc., and alkylcarbonyl groups having 2 to 13 carbon atoms. Examples of the alkyl group include an acetyl group, a propionyl group, and a butyryl group, and the alkyl group has 2 to 1 carbon atoms. The alkylcarbonyloxy group of 3 includes an acetyloxy group, a propionyloxy group, butyryloxy group and the like. L 1 is a single bond or an alkanediyl group having 1 to 4 carbon atoms which may have a substituent. is preferably a single bond or an alkanediyl group having 1 to 4 carbon atoms which may have a halogen atom. It is more preferable that the alkane having 1 to 4 carbon atoms may have a single bond or a fluorine atom. A diyl group is more preferred, and a single bond, -C(CH3)2- or -C(CF3) 2- is even more preferred.

[0011] R 1 Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. It can be obtained. R 1 The haloalkyl group having 1 to 12 carbon atoms is a group having 1 to 12 carbon atoms and a halogen atom. 12 alkyl groups, including fluorinated alkyl groups having 1 to 12 carbon atoms, chlorinated alkyl groups having 1 to 12 carbon atoms, alkyl groups, bromoalkyl groups having 1 to 12 carbon atoms, and iodinated alkyl groups having 1 to 12 carbon atoms. The haloalkyl group may be a perfluoroalkyl group having 1 to 12 carbon atoms (trifluoroalkyl group). fluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, nonafluorobutyric acid group, ethyl group, etc.), 2,2,2-trifluoroethyl group, 3,3,3-trifluoropropyl group , 4,4,4-trifluorobutyl group, and 3,3,4,4,4-pentafluorobutyl Examples of the haloalkyl group include a chloromethyl group, a bromomethyl group, and an iodomethyl group. The number of carbon atoms in is preferably 1 to 9, more preferably 1 to 6, and even more preferably It is 1 to 4, and even more preferably 1 to 3. R 1 is a hydrogen atom, an iodine atom, a fluorine atom, a bromine atom, or a haloalkyl group having 1 to 6 carbon atoms. A hydrogen atom, an iodine atom, a fluorine atom or a perfluoroalkyl group having 1 to 3 carbon atoms is preferred. An alkyl group is more preferred, and a hydrogen atom, an iodine atom, a fluorine atom or a trifluoromethyl group is is more preferred, and an iodine atom is even more preferred. R 1 is the L bonded to the benzene ring 1 The term "ortho, meta, or para" refers to a bond that occurs in any of the positions. However, it is preferable that the bond is at the ortho or meta position.

[0012] X 1 The alkanediyl group in the formula (I) is 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 6-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 2-methylbutane-1,4-diyl groups. The lucanediyl group preferably has 1 to 4 carbon atoms, and more preferably 1 to 3 carbon atoms. The —CH2— contained in the alkanediyl group is —O—, —S—, —CO—, —SO—, or -SO2- may be replaced by -CH2- in the alkanediyl group. , -S-, -CO-, -SO- or -SO2-, the group before replacement The carbon number is the carbon number of the alkanediyl group. -CH2- in the alkanediyl group is -O-, -S-, -CO-, -SO- or The group substituted for -SO2- is a carbonyloxy group (- contained in an ethylene group). CH2-CH2- is replaced by -O-CO-), alkanediyloxy group (alkane a group in which any -CH2- at any position in a benzyl group is replaced with -O-), alkanediyloxycarbonyl group (-CH2-C at any position in the alkanediyl group) H2- is replaced by -O-CO-), alkanediylcarbonyl group (alkanedi a group in which any -CH2- in an alkane group is replaced with -CO-), Diylcarbonyloxy group (-CH2-CH2 at any position in the alkanediyl group) - is replaced by -CO-O-), alkanediylthio group (alkanediyl group A group in which any -CH2- at any position contained therein is replaced with -S-), alkanediylsulfo -nyl group (-CH2- at any position in the alkanediyl group is replaced by -SO2- Examples include the group (a group in which the aryl group is substituted). Examples of the alkanediyloxy group include a methyleneoxy group, an ethyleneoxy group, a propyleneoxy group, and a propyleneoxy group. Examples thereof include an oxy group and a butyleneoxy group. Alkanediyloxycarbonyl group, alkanediylcarbonyl group and alkanediyl The carbonyloxy group is a group obtained by adding a carbonyl group to the above-mentioned alkanediyl group or alkanediyloxy group. It represents a group to which a hydroxyl group or a carbonyloxy group is bonded. Examples of the alkanediyloxycarbonyl group include a methyleneoxycarbonyl group, an ethylene oxycarbonyl group, butyleneoxycarbonyl group, etc., and alkanediylcarbonyl group Examples of the olefin group include an ethylene carbonyl group, a propylene carbonyl group, and a butylene carbonyl group. The alkanediylcarbonyloxy group includes an ethylenecarbonyloxy group. oxy group, propylenecarbonyloxy group, butylenecarbonyloxy group, etc. Examples of the alkanediylthio group include a methylenethio group, an ethylenethio group, and a propylenethio group. Examples of the alkanediylsulfonyl group include a methylenesulfonyl group and an ethylenesulfonyl group. Examples thereof include a phenyl group and a propylenesulfonyl group. X 1 is an alkanediyl group having 1 to 6 carbon atoms which may have a substituent (the alkanediyl group -CH2- in the formula (I) is replaced by -O-, -S-, -CO-, -SO- or -SO2-. may be -O-, -S-, -CO-, -SO- or -SO2- Preferably, the alkanediyl group has 1 to 4 carbon atoms (the —CH2— contained in the alkanediyl group). may be replaced by -O-, -S-, -CO-, -SO- or -SO2-), More preferably, it is -O-, -S-, -CO-, -SO- or -SO2-, and has 2 carbon atoms. More preferably, it is a branched alkanediyl group having 1 to 4 carbon atoms or -O-.

[0013] R 2 The substituents that Ph may have include a halogen atom, a hydroxy group, a cyano group, Carboxy group, alkyl group having 1 to 12 carbon atoms, haloalkyl group having 1 to 12 carbon atoms, carbon number Examples include alkoxy groups of 1 to 12 and groups in which two or more of these groups are combined. Examples of halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. do. Examples of the alkyl group having 1 to 12 carbon atoms include a methyl group, an ethyl group, a propyl group, and an isopropyl group. butyl, isobutyl, tert-butyl, pentyl, hexyl, octyl The number of carbon atoms in the alkyl group is preferably 1 to 9, and more preferably 1 to 9. Preferably, it is 1 to 6, more preferably 1 to 4, and even more preferably 1 to 3 is. A haloalkyl group having 1 to 12 carbon atoms is an alkyl group having 1 to 12 carbon atoms and a halogen atom. It represents a fluorinated alkyl group having 1 to 12 carbon atoms, a chlorinated alkyl group having 1 to 12 carbon atoms, a carboxylic acid group, Examples include alkyl bromides having 1 to 12 carbon atoms and alkyl iodides having 1 to 12 carbon atoms. The alkyl group may be a perfluoroalkyl group having 1 to 12 carbon atoms (e.g., trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl 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 The carbon number of the haloalkyl group is, for example, Preferably, it is 1 to 9, more preferably 1 to 6, and even more preferably 1 to 4. and even more preferably 1 to 3. Examples of the alkoxy group having 1 to 12 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, a bromine group, and a methyl group. hexyloxy, pentyloxy, hexyloxy, octyloxy, 2-ethylhexyl hydroxyl group, nonyloxy group, decyloxy group, undecyloxy group, dodecyloxy group The number of carbon atoms in the alkoxy group is preferably 1 to 6, and more preferably 1 to 4, and even more preferably 1 to 3. Examples of the group combining two or more of these include an alkoxycarbonyl group having 2 to 13 carbon atoms, a carbon alkylcarbonyl groups having 2 to 13 carbon atoms and alkylcarbonyloxy groups having 2 to 13 carbon atoms, etc. Examples include: Alkoxycarbonyl groups having 2 to 13 carbon atoms, alkylcarbonyl groups having 2 to 13 carbon atoms, and and alkylcarbonyloxy groups having 2 to 13 carbon atoms are the same as the above-mentioned alkyl or alkoxy groups. It represents a group in which a carbonyl group or a carbonyloxy group is bonded to a silyl group. Examples of the alkoxycarbonyl group having 2 to 13 carbon atoms include a methoxycarbonyl group, an ethoxy group, and carbonyl group, butoxycarbonyl group, etc., and alkylcarbonyl groups having 2 to 13 carbon atoms. Examples of the alkyl group include an acetyl group, a propionyl group, and a butyryl group, and the alkyl group has 2 to 1 carbon atoms. The alkylcarbonyloxy group of 3 includes an acetyloxy group, a propionyloxy group, The number of carbon atoms of the alkoxycarbonyl group is preferably 2 to 6. It is preferably 6, more preferably 2 to 4, and even more preferably 2 or 3. The carbonyl group preferably has 2 to 6 carbon atoms, more preferably 2 to 4 carbon atoms, Preferably, it is 2 or 3. The number of carbon atoms in the alkylcarbonyloxy group is preferably 2 to 6. is more preferably 2 to 4, and further preferably 2 or 3. R 2 The substituent that Ph may have is a halogen atom, a hydroxy group, a group having 1 to 10 carbon atoms, or an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms. It is preferable that the alkyl group is a halogen atom or a fluorinated alkyl group having 1 to 6 carbon atoms. Preferably, it is a fluorine atom, an iodine atom, or a perfluoroalkyl group having 1 to 3 carbon atoms. is more preferred, and a fluorine atom, an iodine atom or a trifluoromethyl group is even more preferred. is more preferred. R 2 is *-L 1 -OH (where L 1 is a single bond or a group having 1 carbon atom which may have a substituent. It is preferably an alkanediyl group having a carbon number of 1 to 4, which may have a single bond or a halogen atom. It is more preferably an alkanediyl group having 1 to 4 carbon atoms, and has a single bond or a fluorine atom. More preferably, it is an alkanediyl group having 1 to 4 carbon atoms, which may be a single bond, -C Even more preferably, it is —(CH3)2— or —C(CF3)2—. 1 -Ph-L 1 -OH (where X 1 is an alkanediyl group having 1 to 4 carbon atoms (the alkanediyl The yl group may be replaced by -O-, -S-, -CO-, -SO- or -SO2-. -O-, -S-, -CO-, -SO- or -SO2- is preferred, and carbon L is more preferably a branched alkanediyl group having 2 to 4 carbon atoms or -O-. 1 is a one-line It is preferably an alkanediyl group having 1 to 4 carbon atoms which may have a substituent, or a single alkanediyl group which may have a substituent. It is more preferably an alkanediyl group having 1 to 4 carbon atoms which may have a bond or a halogen atom. Preferably, it is a single bond or an alkanediyl group having 1 to 4 carbon atoms which may have a fluorine atom. It is more preferable that the group is a single bond, -C(CH3)2- or -C(CF3)2-. is even more preferred. Ph is X 1 - and -L1 One or two substituents other than -OH The substituent of Ph is preferably a halogen atom or a fluorinated alkyl group having 1 to 6 carbon atoms. It is preferably an alkyl group, an iodine atom, a fluorine atom or a perfluoroalkyl group having 1 to 3 carbon atoms. More preferably, it is an alkyl group, an iodine atom, a fluorine atom or a trifluoromethyl It is more preferable that the alkyl group is an alkyl group, and it is even more preferable that the alkyl group is an iodine atom. It is preferable that In addition, R 2 is the L bonded to the benzene ring 1 This means that the molecule is in the ortho, meta, or para position. However, it is preferred that at least one of them is bonded to the meta or para position. Also, R 2 *-X 1 -Ph-L 1 If the X is -OH, it will bind to Ph. 1 and L 1 The term "ortho-, meta-, or para-position" refers to a group of aryl groups bonded to a hydroxyl group at the ortho, meta, or para position. It is preferable that

[0014] R 3 Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. It can be obtained. R 3 The haloalkyl group having 1 to 12 carbon atoms is a group having 1 to 1 carbon atoms and a halogen atom. 2 alkyl group, and fluorinated alkyl groups having 1 to 12 carbon atoms, chlorinated alkyl groups having 1 to 12 carbon atoms, alkyl groups, bromoalkyl groups having 1 to 12 carbon atoms, and iodinated alkyl groups having 1 to 12 carbon atoms. The haloalkyl group may be a perfluoroalkyl group having 1 to 12 carbon atoms (e.g., trifluoroalkyl groups). Fluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, nonafluorobutyl group 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 number of carbon atoms is preferably 1 to 9, more preferably 1 to 6, and even more preferably 1. to 4, and even more preferably 1 to 3. R 3 Examples of the alkyl group having 1 to 12 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, and an isopropyl group. Propyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, hexyl group, Examples of the alkyl group include an octyl group and a nonyl group. The number of carbon atoms in the alkyl group is preferably It is 1 to 9, more preferably 1 to 6, even more preferably 1 to 4, and even more preferably More preferably, it is 1 to 3. R 3 In the case where -CH2- in the alkyl group is replaced by -O- or -CO-, In this case, the number of carbon atoms before substitution is the total number of carbon atoms in the alkyl group. Hydroxy group (a group in which -CH2- in a methyl group is replaced with -O-), carbo an oxy group (an ethyl group in which -CH2-CH2- is replaced with -O-CO-); Alkoxy group (an alkyl group in which -CH2- at any position is replaced with -O-) alkoxycarbonyl group (a group in which -CH2-CH2 is present at any position in the alkyl group) - is replaced by -O-CO-), alkylcarbonyl group (a group contained in an alkyl group a group in which any one of -CH2- at any position is replaced by -CO-), alkylcarbonyloxy A group (where -CH2-CH2- at any position in the alkyl group is replaced with -CO-O-) and groups in which two or more of these groups are combined. The alkoxy group includes an alkoxy group having 1 to 11 carbon atoms, for example, methoxy. groups, ethoxy groups, propoxy groups, butoxy groups, pentyloxy groups, hexyloxy groups, etc. The alkoxy group preferably has 1 to 6 carbon atoms, more preferably 1 to 4 carbon atoms. and more preferably 1 to 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. The alkoxycarbonyl group includes an alkoxycarbonyl group having 2 to 11 carbon atoms. Examples of such groups include methoxycarbonyl, ethoxycarbonyl, and butoxycarbonyl groups. Examples of the alkylcarbonyl group include alkylcarbonyl groups having 2 to 12 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 11 carbon atoms. Examples thereof include an acetyloxy group, a propionyloxy group, and a butyryloxy group. The alkoxycarbonyl group preferably has 2 to 6 carbon atoms, more preferably 2 to 6 carbon atoms. The number of carbon atoms in the alkylcarbonyl group is preferably 4, and more preferably 2 or 3. It is preferably 2 to 6, more preferably 2 to 4, and even more preferably 2 or 3. The number of carbon atoms in the alkylcarbonyloxy group is preferably 2 to 6, more preferably 2 to 4. and more preferably 2 or 3. R 3 are each independently preferably a halogen atom, a hydroxy group, a halogen atom having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms (wherein the —CH2— contained in the alkyl group is — may be replaced by -O- or -CO-), and more preferably a fluorine atom, an iodide atom, A hydrogen atom, a hydroxy group, a fluorinated alkyl group having 1 to 3 carbon atoms, or an alkyl group having 1 to 3 carbon atoms (The —CH2— contained in the alkyl group may be replaced by —O— or —CO—. ), more preferably a fluorine atom, an iodine atom or a trifluoromethyl group; More preferred is a fluorine atom or an iodine atom. m2 is preferably an integer of 1 to 3, more preferably 1 or 2, and even more preferably 1. Desirable. m3 is preferably 0, 1 or 3.

[0015] Examples of the compound (I) include compounds represented by the following formula: TIFF2026010138000007.tif155166

[0016] TIFF2026010138000008.tif200169

[0017] TIFF2026010138000009.tif199170

[0018] TIFF2026010138000010.tif116163

[0019] The content of compound (I) is usually 0.001 to 20% based on the solid content of the resist composition. % by mass, preferably 0.005 to 15% by mass, more preferably 0.01 to 10% by mass. do.

[0020] <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:

[0021] <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. TIFF2026010138000011.tif1988[In formula (1), R a1 , R a2 and R a3 are each independently an alkyl group having 1 to 8 carbon atoms. alkyl groups having 2 to 8 carbon atoms, alicyclic hydrocarbon groups having 3 to 20 carbon atoms, and alkyl groups having 6 to 1 carbon atoms. 8 or a combination thereof, or R a1 and R a2 are bonded to each other and form a non-aromatic hydrocarbon ring of 3 to 20 carbon atoms together with the carbon atom to which they are attached. . ma and na each independently represent 0 or 1, and at least one of ma and na represents 1. * denotes a binding site.] TIFF2026010138000012.tif2171[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 ring is formed, and -CH2- contained in the hydrocarbon group and the heterocyclic ring is -O- or -S- may be replaced by . X represents an oxygen atom or a sulfur atom. na' represents 0 or 1. * denotes a binding site.]

[0022] 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 The alkenyl group in the formula (I) is an ethenyl group or a propenyl group. , isopropenyl group, butenyl group, isobutenyl group, tert-butenyl group, pentenyl Examples of the octenyl group include a hexenyl group, a heptenyl group, an octenyl group, an isooctenyl group, and a nonenyl group. can be done. 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 Ra3 Alicyclic carbonization of The hydrogen group preferably has 3 to 16 carbon atoms. TIFF2026010138000013.tif10150R 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 ) includes the following rings. The non-aromatic hydrocarbon ring is preferably a carbon The numbers are 3 to 12. * indicates the bonding site with -O-. TIFF2026010138000014.tif31139

[0023] 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 ring, -C(R a1’ )(R a2’ )-XR a3’ Examples of rings include the following: * indicates a binding site. TIFF2026010138000015.tif18130R a1’ and R a2’ At least one of these is preferably a hydrogen atom. na' is preferably 0.

[0024] 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 n A group where a=1. As the group, a tert-butoxycarbonyl group is preferred. 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. TIFF2026010138000016.tif154163

[0025] Specific examples of group (2) include the following groups: * represents a binding site. TIFF2026010138000017.tif55153

[0026] 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.

[0027] 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.

[0028] As a structural unit derived from a (meth)acrylic monomer having a group (1), 0) (hereinafter, may be referred to as structural unit (a1-0)), -1) (hereinafter, may be referred to as structural unit (a1-1)) or a structural unit represented by the formula ( a1-2) (hereinafter, sometimes referred to as structural unit (a1-2)) The resin (A) preferably contains the structural unit (a1-0), the structural unit (a1-1), and and at least one structural unit selected from the group consisting of structural units (a1-2), Preferably, the structural unit (a1-1) is a structural unit (a1-2) selected from the group consisting of the structural unit (a1-1) and the structural unit (a1-2). These may be used alone or in combination of two or more. It may also be used. TIFF2026010138000018.tif46150 [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.

[0029] 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 and R a04 alkyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups, and and groups combining these groups, R in group (1) a1 , R a2 and R a3 Similar to the groups listed in Examples include groups. R a6 and R a7Alkyl groups, alkenyl groups, alicyclic hydrocarbon groups, aromatic hydrocarbon groups The hydrogen group and the group formed by combining these groups include R a1 , R a2 and R a3 The groups listed in Similar groups can be mentioned. R a02 , R a03 , and R a04 The alkyl group in It is an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group or an ethyl group, A methyl group is preferred. 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, Preferably, it is an ethyl group or an isopropyl 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 are each independently preferably an alkyl group having 1 to 6 carbon atoms, It is preferably an alkenyl group having 2 to 6 carbon atoms or an aromatic hydrocarbon group having 6 to 12 carbon atoms, more preferably a methyl group. butyl group, ethyl group, isopropyl group, t-butyl group, ethenyl group, phenyl group or naphthyl group and more preferably an ethyl group, an isopropyl group, a t-butyl group, an ethenyl group, or is a phenyl group. 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.

[0030] 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. TIFF2026010138000019.tif98165

[0031] 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. TIFF2026010138000020.tif41168

[0032] 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. TIFF2026010138000021.tif71168

[0033] When the resin (A) contains the structural unit (a1-0), its content is determined based on the total structural units of the resin (A). It is usually 5 to 80 mol %, preferably 5 to 75 mol %, more preferably The content is usually 10 to 70 mol %. When the resin (A) contains the structural unit (a1-1) and / or the structural unit (a1-2), The total content of these is usually 10 to 90 mol % based on the total structural units of the resin (A), and preferably It is preferably 15 to 85 mol %, more preferably 20 to 80 mol %, and even more preferably Preferably, it is 20 to 75 mol %, and even more preferably, it is 20 to 70 mol %.

[0034] 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)"). TIFF2026010138000022.tif4461[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.]

[0035] 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. Ra33 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.

[0036] *-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.

[0037] Examples of the alkanediyl group include a methylene group, an ethylene group, and 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-methylpropane-1, 3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1,4-diyl group and and 2-methylbutane-1,4-diyl group. A a32 is preferably a methylene group or an ethylene group.

[0038] 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.

[0039] 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. 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: TIFF2026010138000023.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:

[0040] 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. -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.

[0041] 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 structural unit in which the corresponding hydrogen atom is replaced by a halogen atom, a haloalkyl group, or an alkyl group. More preferably, the formula (a1-4-1) to the formula (a1-4-5) and the formula (a1- 4-10), formula (a1-4-13), formula (a1-4-14), formula (a1-4-19), formula Examples of structural units are those represented by (a1-4-20). TIFF2026010138000024.tif131165

[0042] 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 3 to 80 mol %, more preferably 5 to 75 mol %, based on the total of the units. More preferably, the content is 7 to 70 mol %, and even more preferably, 7 to 65 mol %. It is even more preferable that the content is 10 to 60 mol %.

[0043] 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. TIFF2026010138000025.tif4558 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.

[0044] 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 an ethyl group. group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, fluoro group Examples of such groups 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—.

[0045] 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. TIFF2026010138000026.tif33133

[0046] 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.

[0047] Further, examples of the structural unit (a1) include the following structural units. TIFF2026010138000027.tif31162

[0048] 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.

[0049] Further, examples of the structural unit (a1) include the following structural units. TIFF2026010138000028.tif4994When resin (A) contains structural units such as (a1-6-1) to (a1-6-3) above The content thereof is preferably 10 to 60 mol % based on the total structural units of the resin (A), and more preferably 15 to 60 mol %. More preferably, the content is 20 to 55 mol %, even more preferably, 20 to 50 mol %, and 20 to 45 mol %. It is even more preferable, and 20 to 40 mol % is particularly preferable.

[0050] <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.

[0051] <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) is 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.

[0052] 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. TIFF2026010138000029.tif4854[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.

[0053] 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.

[0054] *-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.

[0055] 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.

[0056] 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.

[0057] mb is preferably 0, 1 or 2, more preferably 0 or 1, and even more preferably 0. The hydroxy group is preferably bonded to the m-position or p-position of the benzene ring, and When the phenyl group has two or more hydroxy groups, it is more preferable that the two The hydroxy groups are preferably bonded to the m-position and the p-position, respectively.

[0058] 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 the 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. TIFF2026010138000030.tif79169

[0059] 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.

[0060] 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: TIFF2026010138000031.tif4562 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.

[0061] 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.

[0062] 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. TIFF2026010138000032.tif49135

[0063] 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 %.

[0064] <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:

[0065] 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. TIFF2026010138000033.tif50160 [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 -C It represents a group represented by OO-(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 or different from each other.

[0066] R a21 , R a22 , R a23 and R a25 The aliphatic hydrocarbon group in butyl, sec-butyl and tert-butyl groups. Examples include alkyl groups such as t-butyl groups. R a24 The halogen atoms in the formula (I) include fluorine, chlorine, bromine and iodine. 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.

[0067] 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.

[0068] 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 one of 1 to 4 A group in which each of the integers is 0 or 1, more preferably -O- and *-O-CH2-CO-O-, even more preferably Preferably it is an oxygen atom. R a18 ~R a21 is preferably a methyl group. R a22 and R a23 are each independently preferably a carboxy group, a cyano group or a methyl group. 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.

[0069] In formula (a3-4), R a24 is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. A hydrogen atom, a methyl group, or an ethyl group is more preferred. 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)'. TIFF2026010138000034.tif3849 (in the formula, R a24 , L a7 has the same meaning as above.)

[0070] The structural unit (a3) ​​may be a monomer described in JP-A-2010-204646. , monomers described in JP-A-2000-122294, 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 Structural units that replace elementary atoms are preferred.

[0071] TIFF2026010138000035.tif116165

[0072] 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 %.

[0073] <Structural unit (a4)> Examples of the structural unit (a4) include the following structural units. TIFF2026010138000036.tif2862[In formula (a4), R 41 represents a hydrogen atom or a methyl group. R 42 represents a saturated hydrocarbon group having 1 to 24 carbon atoms and containing a halogen atom, The —CH2— contained in the radical may be replaced by —O— or —CO—. R 42 The saturated hydrocarbon group represented by the formula (I) is a chain saturated hydrocarbon group and a monocyclic or polycyclic alicyclic saturated hydrocarbon group. Examples of the hydrocarbon group include hydrocarbon groups and groups formed by combining these groups.

[0074] 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. TIFF2026010138000037.tif10146 The group formed by the combination may include 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.

[0075] The structural unit (a4) may be a structural unit represented by formula (a4-0), a structural unit represented by formula (a4-1), and a structural unit represented by formula (a4-4). TIFF2026010138000038.tif4551[In formula (a4-0), R 54 represents a hydrogen atom or a methyl group. L 4a represents a single bond or an alkanediyl 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 64 represents a hydrogen atom or a fluorine atom.

[0076] L 4a The alkanediyl group in the formula (I) includes a methylene group, an ethylene group, a propane-1, linear alkanediyl groups such as butane-1,3-diyl and butane-1,4-diyl; -diyl group, propane-1,2-diyl group, butane-1,3-diyl group, 2-methylpropane Branched alkanes such as pan-1,3-diyl and 2-methylpropane-1,2-diyl groups An example is a diyl group.

[0077] L 3a The perfluoroalkanediyl group in Fluoroethylene group, perfluoroethylfluoromethylene group, perfluoropropane- 1,3-diyl group, perfluoropropane-1,2-diyl group, perfluoropropane- 2,2-diyl group, perfluorobutane-1,4-diyl group, perfluorobutane-2, 2-diyl group, perfluorobutane-1,2-diyl group, perfluoropentane-1,5 -diyl group, perfluoropentane-2,2-diyl group, perfluoropentane-3,3 -diyl group, perfluorohexane-1,6-diyl group, perfluorohexane-2,2 -diyl group, perfluorohexane-3,3-diyl group, perfluoroheptane-1,7 -diyl group, perfluoroheptane-2,2-diyl group, perfluoroheptane-3,4 -diyl group, perfluoroheptane-4,4-diyl group, perfluorooctane-1,8 -diyl group, perfluorooctane-2,2-diyl group, perfluorooctane-3,3 -diyl group, perfluorooctane-4,4-diyl group, and the like. L 3a The perfluorocycloalkanediyl group in perfluorocyclopentanediyl group, perfluorocycloheptanediyl group yl group, perfluoroadamantanediyl group, and the like.

[0078] 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.

[0079] The structural unit (a4-0) may be the following structural unit or a structural unit ( a4-0) in R 54 The structural unit in which the methyl group corresponding to can be. JPEG2026010138000039.jpg95166

[0080] TIFF2026010138000040.tif4866[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). TIFF2026010138000041.tif1488 [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 represents a single bond or a divalent saturated hydrocarbon group having 1 to 5 carbon atoms which may have a substituent. Represents. X a41 and X a42 are 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 ]

[0081] 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.

[0082] 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. TIFF2026010138000042.tif10160The group formed by the combination may include 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.

[0083] R a42 The substituents of the formula (a-g3) include halogen atoms and groups represented by the formula (a-g3). The halogen atom may be at least one selected from the group consisting of fluorine atom, Examples include a chlorine atom, a bromine atom, and an iodine atom, and preferably a fluorine atom. TIFF2026010138000043.tif855[In formula (a-g3), X a43 represents an oxygen atom, a carbonyl group, *-O-CO- or *-CO-O-. A a45 represents a saturated hydrocarbon group having 1 to 17 carbon atoms which may have a halogen atom. * denotes 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 a saturated hydrocarbon group having 1 to 17 carbon atoms and at least one halogen atom.

[0084] A a45 The saturated hydrocarbon group in the formula (I) is a methyl group, an ethyl group, a propyl group, or a butyl group. , pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, pentadeca Alkyl groups such as silyl, 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): TIFF2026010138000044.tif10160The group formed by the combination may include 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.

[0085] R a42 is preferably a saturated hydrocarbon group which may have a halogen atom, and / or a saturated hydrocarbon group having a group represented by formula (a-g3) More preferable. R a42 When is a saturated hydrocarbon group having a halogen atom, it is preferably a saturated hydrocarbon group having a fluorine atom. It is preferably a saturated hydrocarbon group having a fluorocarbon group, more preferably a perfluoroalkyl group or a perfluorosilyl group. Preferably, the alkyl group is a chloroalkyl group, more preferably a perfluoroalkyl group having 1 to 6 carbon atoms. Particularly preferred is a perfluoroalkyl group having 1 to 3 carbon atoms. Examples of the fluoro groups include perfluoromethyl, perfluoroethyl, and perfluoropropyl groups. , perfluorobutyl group, perfluoropentyl group, perfluorohexyl group, perfluoro Examples of perfluorocycloalkyl groups include perfluoroheptyl and perfluorooctyl groups. Examples of the cyclohexyl group include a perfluorocyclohexyl group. R a42 is a saturated 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 alkyl group has a group represented by formula (a-g3) as a substituent, The number is preferably one.

[0086] R a42 is a saturated hydrocarbon group having a group represented by formula (a-g3), R a42 Yes, More preferred is a group represented by formula (a-g2). TIFF2026010138000045.tif871[In formula (a-g2), A a46 represents a divalent saturated hydrocarbon group having 1 to 17 carbon atoms which may have a halogen atom. represent. X a44 represents **-O-CO- or **-CO-O- (** represents A a46 The binding site represent.). A a47 represents a saturated 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.]

[0087] A a46 The saturated hydrocarbon group preferably has 1 to 6 carbon atoms, and more preferably 1 to 3 carbon atoms. A a47 The saturated hydrocarbon group preferably has 4 to 15 carbon atoms, more preferably 5 to 12 carbon atoms, and A a 47 is more preferably a cyclohexyl group or an adamantyl group.

[0088] 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). TIFF2026010138000046.tif14160

[0089] A a41 The 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 represented by the formula (I) include a hydroxy group and an alkanediyl group having 1 to 10 carbon atoms. Examples of the alkoxy group include alkoxy groups of formula 6. 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.

[0090] A in the group represented by formula (a-g1) a42 , A a43 and A a44 represents the divalent saturated hydrocarbon The element groups include linear or branched alkanediyl groups and monocyclic divalent alicyclic saturated hydrocarbon groups. and a divalent alicyclic saturated hydrocarbon group. Examples of the divalent saturated hydrocarbon groups include methylene groups, ethylene groups, polypropylene groups, and the like. propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, 1-methylpropane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2- Examples include a methylpropane-1,2-diyl group. A a42 , A a43 and A a44 The substituent of the divalent saturated hydrocarbon group represented by is a hydroxy group. and alkoxy groups having 1 to 6 carbon atoms. Preferably, s is 0.

[0091] In the group represented by formula (a-g1), Xa42 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 TIFF2026010138000047.tif46140

[0092] 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: TIFF2026010138000048.tif92135

[0093] TIFF2026010138000049.tif132150

[0094] The structural unit represented by formula (a4-1) includes a structural unit represented by formula (a4-2) and Examples of the structural unit include those represented by formula (a4-3). TIFF2026010138000050.tif4256[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.]

[0095] L 44 The alkanediyl group having 1 to 6 carbon atoms is A a41The same groups as those exemplified in can be. R f6 The saturated hydrocarbon group of R 42 Examples of the groups include the same groups as those exemplified in L 44 The alkanediyl group in the formula (I) is preferably an alkanediyl group having 2 to 4 carbon atoms. An ethylene group is more preferred.

[0096] 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.

[0097] TIFF2026010138000051.tif5671[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 , A f13 and A f14 The total number of carbon atoms in a molecule is limited to 20.

[0098] L5 The alkanediyl group in a41 The same as those exemplified for the alkanediyl group The following groups are mentioned:

[0099] 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.

[0100] 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.

[0101] 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.

[0102] Examples of the structural unit represented by formula (a4-3) include those 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.

[0103] The structural unit (a4) also includes a structural unit represented by formula (a4-4). TIFF2026010138000052.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.]

[0104] R f22 The saturated hydrocarbon group of R a42 Examples include the saturated hydrocarbon groups represented by the following formula: .R f22 is an alkyl group having 1 to 10 carbon atoms and having a fluorine atom, or a carbon atom having a fluorine atom An alicyclic saturated hydrocarbon group having 1 to 10 carbon atoms and a fluorine atom is preferred. An alkyl group is more preferred, and an alkyl group having 1 to 6 carbon atoms and a fluorine atom is even more preferred. It's nice.

[0105] 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.

[0106] 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. JPEG2026010138000053.jpg87160

[0107] When the resin (A) has the structural unit (a4), its content is determined based on the total structural units of the resin (A). The ratio is preferably 1 to 20 mol %, more preferably 2 to 15 mol %, and more preferably 3 to 10 mol % is more preferred.

[0108] <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 the formula (a5-1): . TIFF2026010138000054.tif3555[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 55 represents 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—.

[0109] 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.

[0110] 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.

[0111] 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. TIFF2026010138000055.tif18164 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 , L x6 and L x7 The total number of carbon atoms is 15 or less. In formula (L1-4), Lx8 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.

[0112] 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 x9 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. W x1is preferably a divalent alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms, more preferably , a cyclohexanediyl group, or an adamantanediyl group.

[0113] Examples of the group represented by formula (L1-1) include the divalent groups shown below. TIFF2026010138000056.tif53135

[0114] Examples of the group represented by formula (L1-2) include the divalent groups shown below. TIFF2026010138000057.tif23130

[0115] Examples of the group represented by formula (L1-3) include the divalent groups shown below. TIFF2026010138000058.tif15145

[0116] Examples of the group represented by formula (L1-4) include the divalent groups shown below. TIFF2026010138000059.tif26114

[0117] L 55 is preferably a single bond or a group represented by formula (L1-1).

[0118] 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. TIFF2026010138000060.tif111150When resin (A) has the structural unit (a5), its content is determined based on the total structural units of resin (A). The ratio is preferably 1 to 30 mol %, more preferably 2 to 20 mol %, and more preferably 3 to 15 mol % is more preferred.

[0119] <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.

[0120] 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. TIFF2026010138000061.tif3186

[0121] 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.

[0122] 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.

[0123] 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'). TIFF2026010138000062.tif3172[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.] X11 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.

[0124] The sultone ring is more preferably a ring represented by formula (T1). TIFF2026010138000063.tif3149[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.]

[0125] 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.

[0126] 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. TIFF2026010138000064.tif47144

[0127] The structural unit having a sultone ring preferably has the following group: * in the following group represents the binding site. TIFF2026010138000065.tif45144

[0128] 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.

[0129] The structural unit (a6) is preferably a structural unit represented by formula (Ix). TIFF2026010138000066.tif4956[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.

[0130] 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.

[0131] A xThe 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 cyclohexan-1,4-diyl and cyclooctane-1,5-diyl groups 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.

[0132] R 41 , X11 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:

[0133] Examples of the structural unit (a6) include the following structural units. TIFF2026010138000067.tif92151

[0134] 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.

[0135] <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 include, for example, Examples of the structural units include those described in JP-A-2016-79235, and those having a sulfonyl group in the side chain. A structural unit having a carboxylate group or a carboxylate group and an organic cation, or a sulfonate group in a side chain A structural unit having an aryl group and an organic anion is preferred.

[0136] 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'). TIFF2026010138000068.tif3189[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.

[0137] R III3 The halogen atom represented by the formula (I) includes 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 a8 The 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.

[0138] 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 divalent monocyclic alicyclic saturated hydrocarbon groups such as norbornane-1,4-diyl group, ... Adamantane-2,5-diyl group, Adamantane-1,5-diyl group, Adamantane-2,6- Examples include divalent polycyclic alicyclic saturated hydrocarbon groups such as a diyl group.

[0139] -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 TIFF2026010138000069.tif145161

[0140] 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 8 represents a divalent saturated hydrocarbon group having 1 to 13 carbon atoms.

[0141] ZA + Examples of the organic cation represented by the formula include organic onium cations, organic sulfonium cations, and the like. Thione, organic iodonium cation, organic ammonium cation, benzothiazolium cation Among these, organic sulfonium cations are preferred. Preferred are iodonium cations and organic iodonium cations, and arylsulfonium cations. More preferably, the compound represented by any one of formulas (b2-1) to (b2-4) described below is used. Cation (hereinafter, depending on the formula number, it may be referred to as "cation (b2-1)" etc.) Examples include:

[0142] The structural unit represented by formula (II-2-A') is a structural unit represented by formula (II-2-A) It is preferable that: JPEG2026010138000070.jpg37109 [In formula (II-2-A), R III3 , X III3 and ZA + has the same meaning as above. z 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 z is 2 or more, a plurality of R III2 and R II I4 may be the same 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.]

[0143] R III2 , R III4 , Q a and Q b Perfluoroalkyl groups having 1 to 6 carbon atoms, represented by As the aryl group, the Q b1 The same as the perfluoroalkyl group having 1 to 6 carbon atoms represented by Examples include:

[0144] 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 . TIFF2026010138000071.tif5576 [In formula (II-2-A-1), R III2 , R III3 , R III4 , Q a , Q b , z and ZA + has the same meaning as above represent. R III5 represents a saturated hydrocarbon group having 1 to 12 carbon atoms. 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.

[0145] 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.

[0146] 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 TIFF2026010138000072.tif5287 [In formula (II-2-A-2), R III3 , RIII5 and ZA + has the same meaning as above. m and nA each independently represent 1 or 2.]

[0147] 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 in the formula (I) 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 a fluorine atom (for example, a trifluoromethyl group, etc.); ) and the structural units described in WO 2012 / 050015 ZA + represents an organic cation. TIFF2026010138000073.tif86163

[0148] 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. JPEG2026010138000074.jpg3381 [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 10 carbon atoms which may have a halogen atom 6 represents an alkyl group. A - represents an organic anion. R II1Examples 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 R II3 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.

[0149] Examples of the cation-containing structural unit in formula (II-1-1) include structural units represented by the following formulas: R 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 An alkyl group having 1 to 6 carbon atoms which may have a halogen atom (for example, trifluoromethyl Examples of such structural units include those in which the aryl group is replaced by a methyl group, etc. TIFF2026010138000075.tif85130

[0150] A - Examples of the organic anion represented by the formula include a sulfonate anion, a sulfonylimide anion, and Examples include sulfonylmethide anions, carboxylic acid anions, and the like. - is expressed as The organic anion is preferably a sulfonate anion, and the sulfonate anion is preferably a sulfonate anion as described below. Examples include the anion represented by formula (B1).

[0151] A - Examples of the sulfonylimide anion represented by the formula (I) include the following. TIFF2026010138000076.tif36136

[0152] Examples of sulfonylmethide anions include the following: TIFF2026010138000077.tif29123

[0153] Examples of carboxylate anions include the following: TIFF2026010138000078.tif43156

[0154] Examples of the structural unit represented by formula (II-1-1) include the structural units represented by the following formula: can be done. TIFF2026010138000079.tif88149

[0155] 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 %.

[0156] The resin (A) may have structural units other than the above-mentioned structural units. The moieties include structural units known in the art.

[0157] 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 At least one or two selected from the group consisting of structural units (a1-2), more preferably or at least one selected from the group consisting of structural units (a1-1) and structural units (a1-2). Both are of one or two types. 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 represented by the formula (a2-1): The structural unit (a3) ​​is preferably a structural unit represented by the formula (a2-A). or a structural unit represented by formula (a3-1), a structural unit represented by formula (a3-2) and a structural unit represented by formula (a3-3). a3-4) is at least one selected from the group consisting of structural units represented by the formula:

[0158] 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.

[0159] <Resins other than Resin (A)> The resist composition of the present invention may contain a resin other than the resin (A). 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)).

[0160] 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 (a2), the structural unit (a3) and structural units derived from other known monomers. X) is preferably a resin consisting of only the structural unit (a4) and / or the structural unit (a5). It is more preferable that the resin is composed only of the structural unit (a4). 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). When the resist composition contains resin (X), the content thereof is The content is preferably 1 to 60 parts by mass, more preferably 1 to 50 parts by mass, and further The amount is preferably 1 to 40 parts by mass, even more preferably 1 to 30 parts by mass, and particularly preferably The amount is preferably 1 to 8 parts by mass.

[0161] 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. The content is preferably 90% by mass or more and more preferably 99% by mass or less. The solid content of the product and the resin content relative to it are measured by liquid chromatography or gas chromatography. It can be measured by known analytical means such as graphy.

[0162] <Acid generator (B)> 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., disulfone, ketone 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.

[0163] 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.

[0164] The acid generator (B) is preferably a salt represented by formula (B1) (hereinafter referred to as "acid generator (B1)"). This is sometimes called.) TIFF2026010138000080.tif2859[In formula (B1), Q b1and Q b2 are each independently a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms, It represents an alkyl group or an alkyl 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 -CH2- contained in the carboxylic acid may be replaced by -O- or -CO-, and the divalent saturated carbon atom The hydrogen atom contained in the hydrogen group may be substituted with a fluorine atom or a hydroxy group. Y is a methyl group which may have a substituent or a C3-2 alkyl group 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-. Z + represents an organic cation.

[0165] Q b1 and Q b2 Examples of the perfluoroalkyl group include a trifluoromethyl group, a perfluoromethyl group, and a perfluoromethyl group. perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group perfluoro sec-butyl group, perfluoro tert-butyl group, perfluoro Examples include a pentyl group and a perfluorohexyl group. Q b1 and Q b2 The alkyl group may be a methyl group, an ethyl group, a propyl group, an isopropyl group, or an isopropyl group. butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, etc. Examples include: The acid generator (B) is preferably a fluorine-containing acid generator, b1 and Q b2 Yes, Izu Preferably, either one of them is a fluorine atom or a perfluoroalkyl group, More preferably, they are fluorine atoms or trifluoromethyl groups, and both are fluorine atoms. It is even more preferable that it be a child.

[0166] L b1 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 cyclohexan-1,4-diyl and cyclooctane-1,5-diyl groups 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.

[0167] L b1 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 bonding site with -Y.

[0168] TIFF2026010138000081.tif26117[In formula (b1-1), L b2 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, The hydrogen atoms contained in may be substituted with fluorine atoms. L b3 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, The hydrogen atoms contained in the saturated carbon may be substituted with fluorine atoms or hydroxy groups. The -CH2- contained in the hydrogen hydride group may be replaced by -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, The hydrogen atoms contained in may be substituted with fluorine atoms. L b5 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, The hydrogen atoms contained in the saturated carbon may be substituted with fluorine atoms or hydroxy groups. The -CH2- contained in the hydrogen hydride group may be replaced by -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, The hydrogen atoms contained in may be substituted with fluorine atoms or hydroxy groups. L b7 represents a single bond or a divalent saturated hydrocarbon group having 1 to 23 carbon atoms, The hydrogen atoms contained in the saturated carbon may be substituted with fluorine atoms or hydroxy groups. The -CH2- contained in the hydrogen hydride group may be replaced by -O- or -CO-. However, L b6 and L b7 The total number of carbon atoms is 23 or less.

[0169] 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 b1 The divalent saturated hydrocarbon groups are the same as those of do. L b2 is preferably a single bond. L b3 is preferably a divalent saturated hydrocarbon group having 1 to 4 carbon atoms. L b4 is preferably a divalent saturated hydrocarbon group having 1 to 8 carbon atoms, and the divalent saturated hydrocarbon The hydrogen atoms contained in the 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 hydrogen hydride 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, A hydrogen atom contained in the hydrocarbon group may be substituted with a fluorine atom or a hydroxy group, The -CH2- contained in the divalent saturated hydrocarbon group is replaced with -O- or -CO-. Good too.

[0170] L b1 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). The group represented by formula (b1-1) includes those represented by formulas (b1-4) to (b1-8), respectively. Examples of such groups include: TIFF2026010138000082.tif48120[In formula (b1-4), L b8 represents a single bond or a divalent saturated hydrocarbon group having 1 to 22 carbon atoms, The hydrogen atoms contained in may be substituted with fluorine atoms or hydroxy groups. 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 -CH2- contained therein 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 hydrogen hydride group may be substituted with fluorine atoms or hydroxy groups. However, L b9 and Lb10 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 hydrogen hydride 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 hydrogen hydride 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 hydrogen hydride 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, and the divalent saturated hydrocarbon group The contained -CH2- may be replaced by -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 hydrogen hydride group may be substituted with fluorine atoms or hydroxy groups. However, L b16 ~L b18 The total number of carbon atoms is 19 or less. L b8 is preferably a divalent saturated hydrocarbon group having 1 to 4 carbon atoms. L b9 is preferably a divalent saturated hydrocarbon group having 1 to 8 carbon atoms. L b10 is preferably a single bond or a divalent saturated hydrocarbon group having 1 to 19 carbon atoms, and more preferably 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, and more preferably 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, and more preferably Preferably, it is a single bond or a divalent saturated hydrocarbon group having 1 to 4 carbon atoms.

[0171] 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: TIFF2026010138000083.tif22140[In formula (b1-9), L b19 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. 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.

[0172] 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.

[0173] Examples of the group represented by formula (b1-4) include the following. TIFF2026010138000084.tif17150

[0174] Examples of the group represented by formula (b1-5) include the following. TIFF2026010138000085.tif72149

[0175] Examples of the group represented by formula (b1-6) include the following. TIFF2026010138000086.tif30150

[0176] Examples of the group represented by formula (b1-7) include the following. TIFF2026010138000087.tif64150

[0177] Examples of the group represented by formula (b1-8) include the following. TIFF2026010138000088.tif23150

[0178] Examples of the group represented by formula (b1-2) include the following. TIFF2026010138000089.tif31161

[0179] Examples of the group represented by formula (b1-9) include the following. TIFF2026010138000090.tif44137

[0180] Examples of the group represented by formula (b1-10) include the following. TIFF2026010138000091.tif89157

[0181] Examples of the group represented by formula (b1-11) include the following. TIFF2026010138000092.tif82158

[0182] The alicyclic hydrocarbon group represented by Y includes those represented by formula (Y1) to formula (Y11), formula (Y36) to formula (Y37) Examples include a group represented by formula (Y38). The -CH2- contained in the alicyclic hydrocarbon group represented by Y is -O-, -S-, -SO2- or When is replaced by -CO-, the number may be one or more. Examples of the aryl group include groups represented by formulae (Y12) to (Y35) and (Y39) to (Y43). * is L b1-O- or -CO- in the groups shown below represents a bonding site with - It may be replaced by S- or -SO2-. The alicyclic hydrocarbon group represented by TIFF2026010138000093.tif84165Y is preferably a group represented by formula (Y1) to formula (Y20), Y26), formula (Y27), formula (Y30), formula (Y31), formula (Y39) to formula (Y43) and more preferably a group represented by formula (Y11), formula (Y15), or formula (Y16 ), formula (Y20), formula (Y26), formula (Y27), formula (Y30), formula (Y31), formula (Y 39), a group represented by formula (Y40), formula (Y42) or formula (Y43), and more preferably Or formula (Y11), formula (Y15), formula (Y20), formula (Y26), formula (Y27), formula ( Y30), formula (Y31), formula (Y39), formula (Y40), formula (Y42) or formula (Y43) It is a group represented by the formula: The alicyclic hydrocarbon group represented by Y is selected from the group consisting of the formulas (Y28) to (Y35), (Y39), and (Y 40), formula (Y42) or formula (Y43), etc., when it is a spiro ring containing an oxygen atom, The alkanediyl group between the two oxygen atoms preferably has one or more fluorine atoms. In addition, among the alkanediyl groups contained in the ketal structure, the methylene group adjacent to the oxygen atom is preferably unsubstituted with a fluorine atom.

[0183] The substituent of the methyl group represented by Y is a halogen atom, a hydroxyl group, a methyl group having 3 to 1 carbon atoms, or 6 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 teeth, Alkyl groups having 1 to 16 carbon atoms, alicyclic hydrocarbon groups having 3 to 16 carbon atoms, aromatic hydrocarbon groups having 6 to 18 carbon atoms and the alkyl group and the alicyclic hydrocarbon group are each a cyclic group or a group in which the alkyl group and the alicyclic hydrocarbon group are combined. The —CH2— contained in the 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 each independently selected from the group consisting of aryl, ... may be substituted with a hydroxy group or a fluorine atom; ja is an integer of 0 to 4; ) and others. The substituent of the alicyclic hydrocarbon group represented by Y is a halogen atom, a hydroxy group, a hydroxyl group ... an alkyl group having 1 to 16 carbon atoms which may be substituted with an alkyl group; -CH2- may be replaced by -O- or -CO-), cyclic 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 alkyl groups having 1 to 16 carbon atoms, alicyclic hydrocarbons having 3 to 16 carbon atoms, an alkyl group, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group combining these; The -CH2- contained in the alkyl group and the alicyclic hydrocarbon group is -O-, -SO2- or -CO- and the alkyl group, the alicyclic hydrocarbon group and the aromatic hydrocarbon group may be substituted with The hydrogen atoms contained in may be replaced by hydroxy groups or fluorine atoms. , and represents an integer of 0 to 4.)

[0184] 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-adamantylphenyl group, p-cyclohexyl 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. The group includes 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, and a propyl The alkylsulfonyl group preferably has 1 to 12 carbon atoms. It is preferably 1 to 6, and 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.

[0185] Examples of Y include the following: TIFF2026010138000094.tif160165

[0186] Y is preferably an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent. and more preferably an alicyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent. More preferably, it is an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent, Even more preferably, it is an adamantyl group which may have a substituent, and the alicyclic hydrocarbon The -CH2- constituting the alkyl group or adamantyl group is replaced with -O-, -SO2- or -CO-. Y is preferably an adamantyl group, a hydroxyadamantine group, or a hydroxyadamantyl group. an oxoadamantyl group, an oxoadamantyl group, or a group represented by formula (Y42), formula (Y100) to formula (Y114), It is a group that can be

[0187] The anion in the salt represented by formula (B1) includes the anions represented by formula (B1-A-1) to formula (B1- A-59) (hereinafter, "anion (B1-A-1)" and so on according to the formula number) Formula (B1-A-1) to Formula (B1-A-4), Formula (B1 -A-9), formula (B1-A-10), formula (B1-A-24) ~ formula (B1-A-33), formula (B1-A-36) ~ Formula (B1-A-40), Formula (B1-A-47) ~ Formula (B1-A-5 9) is more preferred. TIFF2026010138000095.tif231164

[0188] TIFF2026010138000096.tif238165

[0189] TIFF2026010138000097.tif168160

[0190] 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 group having 1 to 12 carbon atoms. Preferably, the alkyl group has 1 to 4 carbon atoms, an alicyclic hydrocarbon group has 5 to 12 carbon atoms, or and more preferably a methyl group, an ethyl group, a cyclohexyl group, L is a methyl group or an adamantyl group. A41 is a single bond or an alkanediyl having 1 to 4 carbon atoms. It is a base. Q b1 and Q b2 has the same meaning as above. Specific examples of the anion in the salt represented by formula (B1) include those described in JP-A-2010-20 Examples of anions include those described in JP-A-4646.

[0191] The anion in the salt represented by formula (B1) is preferably a compound represented by formula (B1a-1) to formula (B1a-2). B1a-38) are examples of anions. TIFF2026010138000098.tif238158

[0192] TIFF2026010138000099.tif129154

[0193] Among them, the formulas (B1a-1) to (B1a-3), (B1a-7) to (B1a-1 6), formula (B1a-18), formula (B1a-19), formula (B1a-22) ~ formula (B1a-3) 8) is preferred.

[0194] Z + The organic cations include organic onium cations, organic sulfonium cations, Organic iodonium cations, organic ammonium cations, benzothiazolium cations and Among these, organic sulfonium cations are and organic iodonium cations are preferred, with arylsulfonium cations being more preferred. Specifically, the cation represented by any one of formulas (b2-1) to (b2-4) (hereinafter , and may be referred to as "cation (b2-1)" etc. depending on the formula number. TIFF2026010138000100.tif47170In 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. R b13 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 Rb1 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.

[0195] 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. TIFF2026010138000101.tif11157 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.

[0196] 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.

[0197] 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.

[0198] 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 hydrocarbon group, and an aromatic hydrocarbon group having a chain hydrocarbon group (tolyl group, xylyl group, etc.) phenyl group, cumenyl group, mesityl group, p-ethylphenyl group, p-tert-butylphenyl group group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group, etc.) and alicyclic carbons Aromatic hydrocarbon groups containing hydrogen hydride groups (p-cyclohexylphenyl group, p-adamantyl phenyl group, etc. In addition, when the aromatic hydrocarbon group has a chain hydrocarbon group or an alicyclic hydrocarbon group, A chain hydrocarbon group having 1 to 18 carbon atoms and an alicyclic hydrocarbon group having 3 to 18 carbon atoms are preferred. Examples of aromatic hydrocarbon groups in which hydrogen atoms are substituted with alkoxy groups include p-methoxyphenyl. 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.

[0199] 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.

[0200] 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. TIFF2026010138000102.tif24142

[0201] R 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 b12 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. and preferably a 3- to 7-membered ring. Oxocycloheptane ring, oxocyclohexane ring , oxonorbornane ring, oxoadamantane ring, etc.

[0202] Among the cations (b2-1) to (b2-4), the cation (b2 -1). Examples of the cation (b2-1) include the following cations. TIFF2026010138000103.tif80158

[0203] TIFF2026010138000104.tif102165

[0204] Examples of the cation (b2-2) include the following cations. TIFF2026010138000105.tif19150

[0205] Examples of the cation (b2-3) include the following cations. TIFF2026010138000106.tif26140

[0206] Examples of the cation (b2-4) include the following cations. TIFF2026010138000107.tif153161

[0207] The salt (I) is a combination of the above-mentioned anion and the above-mentioned organic cation, which are optionally The salt (I) is preferably a salt represented by the formula (B1a-1) to the formula (B1a -3), formula (B1a-7) ~ formula (B1a-16), formula (B1a-18), formula (B1a-1 9), an anion represented by any one of formulas (B1a-22) to (B1a-38) and cationic ion (b2-1), cation (b2-2), cation (b2-3) or cation (b2- 4) and the combination thereof.

[0208] 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. TIFF2026010138000108.tif190167

[0209] TIFF2026010138000109.tif250153

[0210] TIFF2026010138000110.tif238165

[0211] In the resist composition of the present invention, the content of the acid generator is 100% by mass of the resin (A) described below. With respect to the amount of the hydroxybenzoate, the amount is preferably 1 part by mass or more and 45 parts by mass or less, and more preferably 3 parts by mass or more and 45 parts by mass or less. It is 0 parts by mass or less, and more preferably 10 parts by mass or more and 40 parts by mass or less.

[0212] <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. 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.

[0213] <Quencher (C)> The quencher (C) is a basic nitrogen-containing organic compound and an acid generated from the acid generator (B). Examples of the acid generating salts include those which generate an acid weaker in acidity than the acid generating the quencher. When (C) is contained, the content of the quencher (C) is based on the solid content of the resist composition. Generally, it is preferably about 0.01 to 15% by mass, and more preferably about 0.01 to 10% by mass. It is more preferable that the content is about 0.1 to 8 mass %, and further more preferable that the content is about 0.1 to 7 mass %. It is even more preferable that the content is about % by mass. 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. 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 amine, 2,2'-dipyridylamine, 2,2'-dipicolylamine, bipyridine, etc. Among them, diisopropylaniline is preferred, and 2,6-diisopropylaniline is more preferred. Propylaniline is an example. Ammonium salts include tetramethylammonium hydroxide, tetraisopropyl ammonium hydroxide, tetrabutylammonium hydroxide, tetrahexyl Ammonium hydroxide, tetraoctylammonium hydroxide, phenyltrimethylammonium hydroxide methylammonium hydroxide, 3-(trifluoromethyl)phenyltrimethylammonium ammonium hydroxide, tetra-n-butylammonium salicylate, and choline. can be done.

[0214] The acidity of a salt that generates an acid weaker than the acid generated from the acid generator (B) is: It is represented by the acid dissociation constant (pKa). A salt that generates an acid weaker in acidity than the acid generated from the acid generator (B) is a salt in which the acid dissociation constant of the acid generated from the salt is usually a salt with -3 < pKa, preferably a salt with -1 < pKa < 7, and more preferably a salt with 0 < pKa < 5. Examples of the salt that generates an acid weaker in acidity than the acid generated from the acid generator (B) include salts represented by the following formula, salts represented by formula (D) described in JP-A-2015-147926 (hereinafter, sometimes referred to as "weak acid intramolecular salt (D)"), and salts described in JP-A-2012-229206 , JP-A-2012-6908, JP-A-2012-72109, JP-A-2011-3 , JP-A-2011-191745. Preferably is a salt that generates a carboxylic acid weaker in acidity than the acid generated from the acid generator (B) (a salt having a carboxylic acid anion), more preferably a weak acid intramolecular salt (D), and even more preferably, among the weak acid intramolecular salts (D), a diphenyliodonium salt containing a phenyl group substituted with a carboxylic acid anion. JPEG2026010138000111.jpg116167

[0215] The weak acid intramolecular salt (D) is preferably a diphenyliodonium salt having an iodonium cation to which two phenyl groups are bonded and a carboxylic acid anion substituted on at least one of the two phenyl groups bonded to the iodonium cation, and examples include salts represented by the following formula. TIFF2026010138000112.tif1493[In formula (D), R and R D1 ​​​​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 and the like. 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. More specifically, the following salts are included: TIFF2026010138000113.tif72165

[0216] <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.

[0217] <Preparation of Resist Composition> The resist composition of the present invention comprises a compound (I), a resin (A), an acid generator (B), and If necessary, a resin other than the resin (A), a solvent (E), a quencher (C), and The composition can be prepared by mixing the other components (F) in any order. There are no particular limitations. The temperature during mixing ranges from 10 to 40°C, depending on the type of resin, etc. An appropriate temperature can be selected depending on the solubility of the resin in the solvent (E). The time can be selected from 0.5 to 24 hours depending on the mixing temperature. The mixing means is not particularly limited, and stirring and mixing, etc., 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

[0218] <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 laser (wavelength 193 nm), 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 (or 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 developing solution. Examples of methods include the dip method, paddle 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 limitations as long as the solvent does not dissolve the resist pattern, and solvents containing 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.

[0219] <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]

[0220] 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 was determined by gel permeation chromatography under the following conditions: value. Device: HLC-8120GPC model (Tosoh Corporation) Column: TSKgel Multipore H XL -M x 3 + guard column (Tosoh) Eluent: tetrahydrofuran Flow rate: 1.0mL / min Detector: RI detector Column temperature: 40℃ Injection volume: 100μl Molecular weight standard: Standard polystyrene (Tosoh Corporation)

[0221] The structure of the compound was also determined by mass spectrometry (LC: Agilent 1100, MASS: A The molecular ion peak was measured using a Gilent LC / MSD. In the following examples, the value of this molecular ion peak is indicated as "MASS."

[0222] 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. TIFF2026010138000114.tif90157

[0223] Synthesis Example 1 [Synthesis of Resin A1] 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. Thereafter, the following was added to the polymerization reaction solution relative to the total mass of all monomers: A 2.0-fold amount of p-toluenesulfonic acid aqueous solution (2.5% by weight) was added and stirred for 12 hours. The recovered organic layer was poured into a large amount of n-heptane to precipitate the resin, and then filtered. By collecting the material, the weight-average molecular weight is reduced to approximately 5.3 x 10 3 Resin A1 was obtained in a yield of 63%. This resin A1 has the following structural units. TIFF2026010138000115.tif37154

[0224] Synthesis Example 2 [Synthesis of Resin A2] 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 Then, 2.0 times the mass of the solution was added to the mixture in an aqueous solution of p-toluenesulfonic acid (2.5% by weight), and the mixture was stirred for 12 hours. After stirring, the mixture was separated. The recovered organic layer was poured into a large amount of n-heptane to precipitate the resin. By filtering and collecting the product, the weight-average molecular weight was reduced to approximately 5.1 × 10 3 Resin A2 was obtained in a yield of 6 Resin A2 was obtained at 1%. This resin A2 has the following structural units. TIFF2026010138000116.tif38154

[0225] Synthesis Example 3 [Synthesis of Resin A3] As the monomers, monomer (a1-2-6), monomer (a2-1-3), monomer ( a3-4-2 and monomer (a1-4-2) were used, and the molar ratio [monomer (a1-2 -6): Monomer (a2-1-3): Monomer (a3-4-2): Monomer (a1-4- 2)) were mixed in a ratio of 53:3:12:32, and then this monomer mixture was The material was mixed with 1.5 times the mass of methyl isobutyl ketone relative to the total mass of all monomers. The resulting mixture was added with azobisisobutyronitrile and azobis(2,4 -dimethylvaleronitrile) based on the total amount of monomers, respectively, at 1.2 mol% and 3.6 mol% vol% of the monomers were added, and the mixture was heated at 73°C for about 5 hours. 2.0 times the total mass of the p-toluenesulfonic acid aqueous solution (2.5 wt%) The mixture was stirred for 12 hours and then separated. The recovered organic layer was poured into a large amount of n-heptane. The resin was precipitated, filtered, and collected to obtain a polymer with a weight-average molecular weight of approximately 5.3 × 10 3 Yes Resin A3 having the following structural units was obtained in a yield of 88%. TIFF2026010138000117.tif37129

[0226] Synthesis Example 4 [Synthesis of Resin A4] 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 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 5.1 × 10 3 Resin A4 was obtained in a yield of 79%. This resin A4 has the following structural units: do. TIFF2026010138000118.tif38129

[0227] Synthesis Example 5 [Synthesis of Resin A5] As monomers, acetoxystyrene, monomer (a1-2-13), monomer (a6 -1) was used, and the molar ratio [acetoxystyrene:monomer (a1-2-13):monomer - (a6-1)] were mixed in a ratio of 35:45:20, and then this monomer - Add 1.5 times the mass of methyl isobutyl ketone to the mixture based on the total mass of all monomers. To the resulting mixture, azobisisobutyronitrile and azobis( 2,4-dimethylvaleronitrile) were added at 1.2 mol% and 3 mol% of the total monomer amount, respectively. 0.6 mol% of methylcellulose was added and heated at 73°C for about 5 hours. 1.5 times the total mass of the monomers, 25% tetramethylammonium hydroxide The aqueous solution of methyl methyl ketone was added, and the mixture was stirred for 12 hours, followed by separation of the layers. The resin was poured into butane to precipitate, and then filtered and collected to obtain a resin with a weight average molecular weight of approximately 5.5x 10 3 Resin A5, which has the following structural units, was obtained in a yield of 79%. That is why. TIFF2026010138000119.tif30126

[0228] Synthesis Example 6 [Synthesis of Resin A6] 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 A6 was obtained in a yield of 74%. This resin A6 has the following structural units: do. TIFF2026010138000120.tif37129

[0229] Synthesis Example 7 [Synthesis of Resin A7] 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 A7 was obtained in a yield of 66%. This resin A7 has the following structural units: do. TIFF2026010138000121.tif37129

[0230] <Preparation of Resist Composition> As shown in Table 1, 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 1]

[0231] <Resin> A1~A7: Resin A1~Resin A7 <Acid generator (B)> B1-43: A salt represented by the formula (B1-43) (the embodiment of JP 2016-47815 A) (Synthesize according to the example) TIFF2026010138000123.tif4381<Compound (I)> I-1: Compound represented by formula (I-1) I-3: Compound represented by formula (I-3) I-6: Compound represented by formula (I-6) I-12: Compound represented by formula (I-12) I-16: Compound represented by formula (I-16) I-25: Compound represented by formula (I-25) I-28: Compound represented by formula (I-28) I-37: Compound represented by formula (I-37) I-46: Compound represented by formula (I-46) I-61: Compound represented by formula (I-61) I-77: Compound represented by formula (I-77) IX-1: Compound represented by formula (IX-1) IX-2: Compound represented by formula (IX-2) IX-3: Compound represented by formula (IX-3) TIFF2026010138000124.tif107168<Quencher (C)> C1: Synthesized by the method described in JP 2011-39502 A TIFF2026010138000125.tif4347<solvent> Propylene glycol monomethyl ether acetate 400 parts Propylene glycol monomethyl ether 100 parts γ-butyrolactone 5 parts

[0232] (Electron beam exposure evaluation of resist composition: butyl acetate 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 fluorine-containing ... 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 1 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. Directly painted. After exposure, post-exposure was performed on a hot plate for 60 seconds at the temperature shown in the "PEB" column of Table 1. 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. Therefore, the line width and space width of the 60 nm line and space pattern are 1:1. The exposure amount was taken as the effective sensitivity.

[0233] 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 2. [Table 2] [Industrial Applicability]

[0234] The resist composition of the present invention reduces the line edge roughness (LE) of the resulting resist pattern. R), it is suitable for semiconductor microfabrication and is extremely useful industrially.

Claims

1. A resist composition comprising a compound represented by formula (I), a resin having an acid labile group, and an acid generator. [In formula (I), L 1 represents a single bond or an alkanediyl group having 1 to 6 carbon atoms which may have a substituent. R １ represents a hydrogen atom, a halogen atom, or a haloalkyl group having 1 to 12 carbon atoms. R ２ is *-X １ -Ph-L １ represents —OH, and * represents the bonding site to the benzene ring. X 1 represents a single bond, an alkanediyl group having 1 to 6 carbon atoms, —O—, —S—, —CO—, —SO— or —SO ２ - represents the -CH contained in the alkanediyl group having 1 to 6 carbon atoms. ２ - is -O-, -S-, -CO-, -SO- or -SO ２ It may be replaced with -. Ph represents a phenylene group which may have a substituent. m2 represents an integer of 1 to 4, and when m2 is 2 or more, a plurality of R ２ may be the same or different from each other. R ３ represents a halogen atom, a hydroxy group, a haloalkyl group having 1 to 12 carbon atoms, or an alkyl group having 1 to 12 carbon atoms, and —CH 2 - may be replaced by -O- or -CO-. m3 represents an integer of 0 to 3, and when m3 is 2 or more, a plurality of R ３ may be the same or different, provided that 1≦m2+m3≦4. However, in formula (I), L １ , R １ , R ２ and R ３ has at least one halogen atom.]

2. L １ 2. The resist composition according to claim 1, wherein is a single bond or an alkanediyl group having 1 to 4 carbon atoms which may have one or more halogen atoms.

3. In formula (I), m2 is 1, R ２ is L in the benzene ring 1 3. The resist composition according to claim 1, wherein the bond is at a meta or para position relative to the bonding position of

4. The Ph is the X １ - and the L １ has one or two substituents other than —OH, 4. The resist composition according to claim 1, wherein the substituents are each independently a halogen atom or a fluorinated alkyl group having 1 to 6 carbon atoms.

5. X 1 is an alkanediyl group having 1 to 4 carbon atoms (the —CH ２ - is -O-, -S-, -CO-, -SO- or -SO ２ -), -O-, -S-, -CO-, -SO- or -SO ２ 5. The resist composition according to claim 1, wherein:

6. R ３ is a fluorine atom, an iodine atom, a hydroxy group, a fluorinated alkyl group having 1 to 3 carbon atoms or an alkyl group having 1 to 3 carbon atoms (the —CH 2 6. The resist composition according to claim 1, wherein - may be replaced by -O- or -CO-.

7. 7. The resist composition according to claim 1, 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.]

8. 8. The resist composition according to claim 1, 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.]

9. In formula (a2-A), At least one hydroxy group is A in the benzene ring a50 9. The resist composition according to claim 8, wherein the bond is at a meta position relative to the bonding position of

10. 10. The resist composition according to claim 1, wherein the acid generator comprises a salt represented by formula (B1). [In formula (B1), Q ｂ１ and Q ｂ２ each independently represents a hydrogen atom, a fluorine atom, a perfluoroalkyl group having 1 to 6 carbon atoms, or an alkyl group having 1 to 6 carbon atoms. L ｂ１ represents a divalent 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 divalent saturated hydrocarbon group may be substituted by a fluorine atom or a hydroxy group. Y 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 It may be replaced by - or -CO-. Z ＋ represents an organic cation.

11. 11. The resist composition according to claim 1, further comprising a salt that generates an acid that is weaker in acidity than the acid generated from the acid generator.

12. (1) a step of applying the resist composition according to any one of claims 1 to 11 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 the steps of:

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