• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
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  • 优先权
    • 专利摘要:
    Disclosed is a resist composition including a compound represented by formula (I) as defined in claim 1, a resin having an acid labile group and an acid generator, wherein in formula (I) , R1 represents a halogen atom or an alkyl fluoride group having 1 to 6 carbon atoms, m1 represents an integer of 1 to 5, and when m1 is 2 or more, a plurality of R1 may be the same or different each other.
    公开号:BE1028078B1
    申请号:E20215162
    申请日:2021-03-03
    公开日:2022-02-11
    发明作者:Satoshi Yamaguchi；Koji Ichikawa；Yukako Anryu
    申请人:Sumitomo Chemical Co；
    IPC主号:
    专利说明:

    [0001] The present invention relates to a resist composition and a method for producing a resist pattern which uses the resist composition.
    [0002] [0002] JP2000-066406A mentions a resist composition including a compound of the following structural formula, a resin having an acid labile group and an acid generator.
    [0003] The present invention proposes to provide a resist composition including a compound capable of producing a resist pattern with a CD (CDU) uniformity which is better than that of a resist pattern formed from a resist composition. including the salts mentioned above.
    [0004] The present invention includes the following resist compositions.
    [0005] [0005]
    [1] [1] A resist composition comprising a compound represented by formula (I), a resin having an acid labile group and an acid generator: OOH
    [2] [2] The resist composition according to [1], wherein R* is a fluorine atom, an iodine atom or a trifluoromethyl group.
    [3] [3] The resist composition according to [1] or [2], wherein m1 is an integer of 1 to 3.
    [4] [4] The resist composition according to any one of [1] to [3], wherein R* includes at least one iodine atom.
    [5] [5] The resist composition according to any one of [1] to [4], wherein the content of compound (I) is 0.001 to 20% by mass based on the solid content.
    [6] [6] The resist composition according to any one of [1] to [5], wherein the resin having an acid labile group includes at least one structural unit selected from the group consisting of a structural unit represented by the formula (a1-1) and a structural unit represented by the formula (a1-2): RE} Jed CC
    [7] [7] The resist composition according to any one of [1] to [6], wherein the resin having an acid labile group includes a structural unit represented by the formula (a2-A): a50 ++ A250 A (a2-A); > OH (RE) where, in the formula (a2-A), R°59 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, R®1 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, A20 represents a single bond or * -X°°1 - (A852-X252) p-, and * represents a bonding site at carbon atoms to which -R° is bonded, A22 represents an alkanediyl group having 1 to 6 carbon atoms, x°°1 and X252 each represent independently -O-, -CO-O- or -O-CO-, nb represents 0 or 1, and mb represents an integer from 0 to 4, and when mb is an integer from 2 or more, a plurality ality of R* may be the same or different from each other.
    [8] [8] The resist composition according to any one of [1] to [7], wherein the acid generator includes a salt represented by the formula (B1): Qh + OS Lb1 2 OS | ALA (BIJ) des where, in the formula (B1), QP! and Q®* each independently represent a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms, LP! represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, -CH>- included in the divalent saturated hydrocarbon group may be replaced by -O- or -CO-, and a hydrogen atom included in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group, Y represents a methyl group which may have a substituent, or an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and -CH>- included in the alicyclic hydrocarbon group can be replaced by -O-, -S (O)>- or -CO-, and Z' represents an organic cation.
    [9] [9] The resist composition according to any one of [1] to [8], further comprising an acid generating salt having an acidity lower than that of an acid generated from the acid generator.
    [10] [10] A method for producing a resist pattern, which comprises: (1) a step of applying the resist composition according to any one of [1] to [9] onto a substrate, (2) a step drying the applied resist composition to form a composition layer, (3) a step of exposing the composition layer, (4) a step of heating the exposed composition layer, and (5) a step of development of the heated composition layer.
    [0006] [0006]
    [0007] [0007] In the present description, “(meth)acrylic monomer” means at least one selected from the group consisting of a monomer having a structure of “CH; =CH-CO-” and a monomer “CH; =C(CH3)-CO-”. Similarly, “(meth)acrylate” and “(meth)acrylic acid” each mean “at least one selected from the group consisting of acrylate and methacrylate” and “at least one selected from the group consisting of acrylic acid and methacrylic acid". When a structural unit having <“CH:=C(CH3)-CO-” or <“CH:=CH-CO-” is exemplified, a structural unit having both groups must be similarly exemplified. "Derived" or "induced" means that a polymerizable C=C bond included in the molecule becomes a -C-C- group by polymerization. In the groups mentioned in the present description, the groups capable of having a linear structure and a branched structure, may have the linear structure or the branched structure. “Combined group” means a group in which two or more exemplified groups are bonded, and the valences of these groups can be changed appropriately depending on a form of bonding. When stereoisomers exist, all stereoisomers are included.
    [0008] <Resist composition> The resist composition according to some embodiments of the present invention includes a compound represented by formula (T) (hereinafter sometimes referred to as "compound (I)>), a resin having a acid-labile group (hereinafter sometimes referred to as "resin (A)") and an acid generator (hereinafter sometimes referred to as acid generator (B)"). “Acid labile group” means a group having a leaving group which is removed by contact with an acid, thereby converting to a constitutional unit having a hydrophilic group (e.g. a hydroxy group or a carboxy group).
    [0009] <Compound (I)> The resist composition according to certain embodiments of the present invention includes a compound (I):
    [0010] [0010] Examples of halogen atom as for Rt include fluorine atom, chlorine atom, iodine atom and bromine atom.
    [0011] [0011] Examples of the compound (I) include the compounds represented by the following formulae.
    [0012] The content of compound (I) is usually 0.001 to 20% by mass, preferably 0.005 to 15% by mass, and more preferably 0.01 to 10% by mass, based on the content. in solids of the resist composition.
    [0013] [0013] <Resin (A)> The resin (A) includes a structural unit having an acid-labile group (hereinafter sometimes referred to as "structural unit (a1)"). It is preferred that the resin (A) includes further a structural unit other than structural unit (a1) Examples of structural unit other than structural unit (a1) include a structural unit having no acid-labile group (hereinafter sometimes referred to as “structural unit(s)"), a structural unit other than the structural unit(al) and the structural unit(s) (e.g. a structural unit having a halogen atom mentioned later (hereinafter sometimes referred to as “ structural unit (a4)"), a structural unit having a non-leaving hydrocarbon group mentioned later (hereinafter sometimes referred to as "structural unit (a5)")), and other structural units derived from monomers known in the art.
    [0014] <Structural unit (a1)> The structural unit (a1) is derived from a monomer having an acid-labile group (hereinafter sometimes referred to as “monomer (ai).
    [0015] [0015] Examples of the alkyl group for R2%, R22 and R°° include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group and octyl group and analogues.
    [0016] [0016] Examples of the hydrocarbon group in RŸ, R° and R include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group and groups formed by combining these groups. Examples of the alkyl group and the alicyclic hydrocarbon group include those which are the same as those mentioned in R*1, R2 and R. Examples of the aromatic hydrocarbon group include an aryl group, such as a phenyl group, a naphthyl group, a anthryl group, a biphenyl group, and a phenanthryl group.
    [0017] [0017] Examples of group (1) include the following groups.
    [0018] [0018] | Specific examples of group (2) include the following groups. * represents a binding position. ADS PP AA CC TO Ar) MO VO pd D TO A
    [0019] The monomer (al) is preferably a monomer having an acid-labile group and an ethylenically unsaturated bond, and more preferably a (meth)acrylic monomer having an acid-labile group.
    [0020] [0020] Among the (meth)acrylic monomers having an acid-labile group, those having an alicyclic hydrocarbon group having 5 to 20 carbon atoms are preferably cited by way of example. When a resin (A) including a structural unit derived from a monomer (a1) having a bulky structure such as an alicyclic hydrocarbon group is used in a resist composition, it is possible to improve the resolution of a resist pattern.
    [0021] The structural unit derived from a (meth)acrylic monomer having a group (1) is a structural unit represented by the formula (a1-0) (hereinafter sometimes referred to as structural unit (a1-0), a structural unit represented by formula (a1-1) (hereinafter sometimes referred to as structural unit (a1-1)) or a structural unit represented by formula (a1-2) (hereinafter sometimes referred to as structural unit (a1-2) ) ).The structural unit is preferably at least one structural unit selected from the group consisting of a structural unit (a1-1) and a structural unit (a1-2).These structural units can be used alone , or two or more structural units can be used in combination.
    [0022] [0022] RO R°* and R°° are preferably a hydrogen atom or a methyl group.
    [0023] The structural unit (a1-0) includes, for example, a structural unit represented by any one of formula (a1-0-1) to formula (a1-0-18) and a structural unit wherein a methyl group corresponding to R*° in the structural unit (a1-0) is substituted by a hydrogen atom and is preferably a structural unit represented by any one of the formula (a1-0-1 ) to the formula (a1-0-10), the formula (a1-0-13) and the formula (a1-0-14).
    [0024] The structural unit (a1-1) includes, for example, structural units derived from the monomers mentioned in JP 2010-204646 A. Among these structural units, a structural unit represented by any one of the formula (a1-1-1) to the formula (a1-1-7) and a structural unit in which a methyl group corresponding to R** in the structural unit (a1-1) is substituted by a hydrogen atom are preferred, and a structural unit represented by any one of formula (a1-1-1) to formula (a1-1-4) is more preferred.
    [0025] [0025] Examples of structural unit (a1-2) include a structural unit represented by any one of formula (a1-2-1) to formula (a1-2-12) and a structural unit in which a methyl group corresponding to R® in the structural unit (a1-2) is substituted by a hydrogen atom and a structural unit represented by any one of formula (a1-2-2), formula (a1-2 -5), formula (a1-2-6) and formula (a1-2-10) to formula (a1-2-12) is preferable.
    [0026] When the resin (A) comprises a structural unit (a1-0), its content is generally from 5 to 80 mol%, preferably from 5 to 75 mol%,
    [0027] [0027] In the structural unit (a1), examples of the structural unit having a group (2) include a structural unit represented by the formula (a1-4) (hereinafter sometimes referred to as "structural unit (a1- 4)>):
    [0028] [0028] Examples of halogen atom in R232 and R233 include fluorine atom, chlorine atom and bromine atom.
    [0029] [0029] Examples of *-X°*-(a2%2-X232),e- include *-O-, *-CO-O-, *-O-CO-, *-CO-0-A332- CO-0-, *-0-CO-A332-0-, *-0-A332-CO-0-, *-CO-0-A%32-0-CO- and *-0-CO-A% 32-0-CO-. Of these, *-CO-0-, *-CO-0-A332-CO-0- or *-O-A3*2_-CO-O- are preferable.
    [0030] Examples of the alkanediyl group include methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane- 1,5-diyl, hexane-1,6-diyl group, butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, a pentane-1,4-diyl group and a 2-methylbutane-1,4-diyl group.
    [0031] [0031] A is preferably a single bond, *-CO-O- or *-CO-O- A332-CO-0-, more preferably a single bond, *-CO-O- or *-CO-O -CHz-CO-O-, and more preferably a single bond or *-CO-O-.
    [0032] la is preferably 0, 1 or 2, more preferably 0 or 1, and more preferably 0.
    [0033] [0033] R33* is preferably a hydrogen atom.
    [0034] [0034] The structural unit (a1-4) includes, for example, the structural units derived from the monomers mentioned in JP 2010-204646 A. The structural unit preferably includes the structural units represented by the formula (a1-4- 1) to the formula (a1-4-18) and a structural unit in which a hydrogen atom corresponding to R23 is substituted with a methyl group, and more preferably structural units represented by the formula (a1-4-1 ) to the formula (a1-4-5), the formula (a1-4-10), the formula (a1-4-13) and the formula (a1-4-14).
    [0035] [0035] When the resin (A) includes the structural unit (a1-4), the content is preferably 3 to 80 mol%, more preferably 5 to 75 mol%, more preferably 7 to 70 mol%, of more preferably 7 to 65 mol%, and more preferably 10 to 60 mol% based on the total of all structural units of the resin (A).
    [0036] [0036] The structural unit derived from a (meth)acrylic monomer having a group (2) also includes a structural unit represented by the formula (a1-5) (hereinafter sometimes referred to as “structural unit (a1-5) "). Lt a8 C SE
    [0037] [0037] The halogen atom includes a fluorine atom and a chlorine atom and is preferably a fluorine atom.
    [0038] [0038] Examples of the structural unit (a1-5) include structural units derived from the monomers mentioned in JP 2010-61117 A. Among these structural units, the structural units represented by the formula (a1-5-1) to formula (a1-5-4) are preferred, and structural units represented by formula (a1-5-1) or formula (a1-5-2) are more preferred.
    [0039] [0039] When the resin (A) includes the structural unit (a1-5), the content is preferably 1 to 50 mol%, more preferably 3 to 45 mol%, more preferably 5 to 40 mol%, and more preferably 5 to 30 mol%, based on all structural units of resin (A).
    [0040] The structural unit (a1) also includes the following structural units.
    [0041] [0041] When the resin (A) includes the structural units mentioned above such as (a1-3-1) to (a1-3-7), the content is preferably 10 to 95 mol%, more preferably 15 to 90 mol% mol%, more preferably 20 to 85 mol%, more preferably 20 to 70 mol%, and more preferably 20 to 60 mol%, based on all structural units of the resin (A ).
    [0042] The structural unit (a1) also includes the following structural units. i Ds Dos D, 0 & O (a1-6-1) (a1-6-2) (a1-6-3) When the resin (A) includes the structural units mentioned above such as (a1-6- 1) to (a1-6-3), the content is preferably 10 to 60 mol%, more preferably 15 to 55 mol%, more preferably 20 to 50 mol%, more preferably 20 to 45 mol %, and more preferably 20 to 40 mol%, based on all structural units of resin (A).
    [0043] [0043] <Structural Unit(s)> The structural unit(s) derives from a monomer having no acid-labile group (hereinafter referred to as "monomer(s)"). It is possible to use as the monomer from which the structural unit(s) derives, a monomer having no acid-labile group known in the resist field.
    [0044] <Structural Unit (a2)> The hydroxy group belonging to the structural unit (a2) may be either an alcoholic hydroxy group or a phenolic hydroxy group. When a resist pattern is produced from the resist composition according to certain embodiments of the present invention, in the case of using, as an exposure source, high energy rays such as an excimer laser KrF (248 nm), electron beam or extreme ultraviolet light (EUV), the structural unit (a2) having a phenolic hydroxy group is preferably used as the structural unit (a2), and it is more preferable to use the structural unit (a2-A) mentioned below. When using an ArF excimer laser (193 nm) or the like, a structural unit (a2) having an alcoholic hydroxy group is preferably used as the structural unit (a2), and it is more preferred to use the structural unit (a2-1) mentioned later. The structural unit (a2) can be included alone, or two or more structural units can be included.
    [0045] In the structural unit (a2), examples of the structural unit having a phenolic hydroxy group include a structural unit represented by the formula (a2-A) (hereinafter sometimes referred to as "structural unit (a2-A )»): R250
    [0046] [0046] Examples of the halogen atom in R3 and R°* include a fluorine atom, a chlorine atom and a bromine atom.
    [0047] Examples of *-X2*!-(a252-X°52)p- include *-O-, *-CO-O-, *-0-CO-, *-CO-0-A92-CO -0-, *-O-CO-A°*°-0-, *-0-A952-CO-0-, *-CO-0-A92-0- CO- and *-O-CO-A® %*-0-CO-. Of these, *-CO-0-, *-CO-O-A®%*-CO-0- or *-O-A352-CO-O- is preferred.
    [0048] Examples of alkanediyl group include methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, pentane group -1,5-diyl, hexane-1,6-diyl group, butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group , a pentane-1,4-diyl group and a 2-methylbutane-1,4-diyl group.
    [0049] A2°0 is preferably a single bond, *-CO-O- or *-CO-O-A3*-CO-O-, more preferably a single bond, *-CO-O- or *- CO-O-CH>-CO-O-, and more preferably a single bond or *-CO-O-.
    [0050] mb is preferably 0, 1 or 2, more preferably 0 or 1, and more preferably 0.
    [0051] [0051]
    [0052] [0052] When the structural unit (a2-A) is included in the resin (A), the content of the structural unit (a2-A) is preferably 5 to 80 mol%, more preferably 10 to 70 mol. %, more preferably 15 to 65 mol%, and more preferably 20 to 65 mol%, based on all structural units.
    [0053] [0053] Examples of the structural unit having an alcoholic hydroxy group in the structural unit (a2) include a structural unit represented by the formula (a2-1) (hereinafter sometimes referred to as “structural unit (a2-1)”) ).
    [0054] In the formula (a2-1), L°* is preferably -O- or -O-(CH2); -CO- O- (fl represents an integer from 1 to 4), and more preferably - O-, R31* is preferably a methyl group, R2!5 is preferably a hydrogen atom, RS is preferably a hydrogen atom or a hydroxy group, and ol is preferably an integer from 0 to 3, and more preferably 0 oul.
    [0055] The structural unit (a2-1) includes, for example, the structural units derived from the monomers mentioned in JP 2010-204646 A. A structural unit represented by any one of the formula (a2-1-1) to the formula (a2-1-6) is preferred, a structural unit represented by any one of the formula (a2-1-1) to the formula (a2-1-4) is more preferred, and a structural unit represented by formula (a2-1-1) or formula (a2-1-3) is more preferred. Ho CHs Ha H Hs CHs Ho H Ho HsG Ha H EE Je De De Du De PE
    [0056] [0056] When the resin (A) includes the structural unit (a2-1), the content is usually 1 to 45 mol%, preferably 1 to 40 mol%, more preferably 1 to 35 mol%, more preferably from 1 to 20 mol%
    [0057] <Structural unit (a3)> The lactone ring belonging to the structural unit (a3) may be a monocyclic ring such as a β-propiolactone ring, a γ-butyrolactone ring or an α-valerolactone ring, or a condensed ring one monocyclic lactone ring and the other ring. Preferably, a γ-butyrolactone ring, an adamantanelactone ring or a bridged ring including a γ-butyrolactone ring structure (eg, a structural unit represented by the following formula (a3-2)) is exemplified.
    [0058] The structural unit (a3) is preferably a structural unit represented by the formula (a3-1), the formula (a3-2), the formula (a3-3) or the formula (a3-4). These structural units may be included alone, or two or more structural units may be included: P 8 7 9 1 fe EE Test Tel fort Sog SE ç y ó en, Ze 0 Ge O
    [0059] [0059] Examples of the aliphatic hydrocarbon group in R°*, R222, R223 and R°°° include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec -butyl and a tert-butyl group.
    [0060] [0060] Examples of alkanediyl group in L® and L® include methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4 -diyl, pentane-1,5-diyl group, hexane-1,6-diyl group, butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane group - 1,2-diyl, a pentane-1,4-diyl group and a 2-methylbutane-1,4-diyl group.
    [0061] In formula (a3-1) to formula (a3-3), preferably, L°* to L°° are each independently -O- or a group in which k3 is an integer from 1 to 4 in *-O-(CH2)(3-CO-O-, more preferably -O- and *-O-CH2-CO-O-, and more preferably an oxygen atom, RAS at R°2! are preferably a methyl group, preferably, R°° and R223 are each independently a carboxy group, a cyano group or a methyl group, and preferably, p1, q1 and r1 are each independently an integer from 0 to 2, and preferably still 0 or 1.
    [0062] In the formula (a3-4), R** is preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, more preferably a hydrogen atom, a methyl group or a group ethyl, and more preferably a hydrogen atom or a methyl group, R225 is preferably a carboxy group, a cyano group or a methyl group, L” is preferably -O- or *-OL°8-CO-O -, and more preferably -O-, -0-CH2-CO-0- or -0-C:H4-CO-0-, and wl is preferably an integer from 0 to 2, and more preferably 0 or .
    [0063] Examples of structural unit (a3) include structural units derived from monomers mentioned in JP 2010-204646 A, monomers mentioned in JP 2000-122294 A and monomers mentioned in JP 2012-41274 A. structure (a3) is preferably a structural unit represented by any one of formula (a3-1-1), formula (a3-1-2), formula (a3-2-1), formula ( a3- 2-2), the formula (a3-3-1), the formula (a3-3-2) and the formula (a3-4-1) to the formula (a3-4-12), and the units structural units in which the methyl groups corresponding to R213, RS, R#20 and R2 * in the formula (a3-1) to the formula (a3-4) are substituted with hydrogen atoms in the above structural units .
    [0064] [0064] CH CHs CHs CH CHs CHs CHs CHs to} JT tt + Jett © 14+ tert tst © oO UX p & +, À, 3 od 8 ö & © à © (a3-1-1) O (a3- 2-1) O4 (a3:200) od 33-1) ET #19 a axis) 332 H2 CH F2 cHs C2 CH < A) SA y Cls C 3 C © + | TX TX | + 2nd + © a 2
    [0065] [0065] When the resin (A) includes the structural unit (a3), the total content is usually 5 to 70 mol%, preferably 10 to 65 mol%, and more preferably 10 to 60 mol%, based on all the structural units of the resin (A).
    [0066] [0066] <Structural unit (a4)> Examples of structural unit (a4) include the following structural units: He R41 = | (a4)
    [0067] [0067] Examples of the chain saturated hydrocarbon group include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl, pentadecyl group, hexadecyl group, heptadecyl group and octadecyl group.
    [0068] [0068] Examples of the structural unit (a4) include a structural unit represented by the formula (a4-0), a structural unit represented by the formula (a4-1), and a structural unit represented by the formula (a4-4 ): R54 bont (4-0) d O 4 / | Sa Les where, in the formula (a4-0), R°* represents a hydrogen atom or a methyl group, L“ represents a single bond or an alkanediyl group having 1 to 4 carbon atoms,
    [0069] [0069] Examples of the alkanediyl group in L* include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group and butane-1,4-diyl group; and branched alkanediyl groups such as ethane-1,1-diyl group, propane-1,2-diyl group, butane-1,3-diyl group, 2-methylpropane-1,3-diyl group and 2-methylpropane-1,2-diyl.
    [0070] [0070] Examples of perfluoroalkanediyl group in L“ include difluoromethylene group, perfluoroethylene group, perfluoroethylfluoromethylene group, perfluoropropane-1,3-diyl group, perfluoropropane-1,2-diyl group, perfluoropropane-2 group, 2-diyl, a perfluorobutane-1,4-diyl group, a perfluorobutane-2,2-diyl group, a perfluorobutane-1,2-diyl group, a perfluoropentane-1,5-diyl group, a perfluoropentane-2 group, 2-diyl, a perfluoropentane-3,3-diyl group, a perfluorohexane-1,6-diyl group, a perfluoro-hexane-2,2-diyl group, a perfluorohexane-3,3-diyl group, a perfluoroheptane- 1,7-diyl, a perfluoroheptane-2,2-diyl group, a perfluoroheptane-3,4-diyl group, a perfluoroheptane-4,4-diyl group, a perfluorooctane-1,8-diyl group, a perfluorooctane- 2,2-diyl, perfluorooctane-3,3-diyl group, perfluorooctane-4,4-diyl group and the like.
    [0071] [0071] L® is preferably a single bond, a methylene group or an ethylene group, and more preferably a single bond or a methylene group.
    [0072] [0072] Examples of the structural unit (a4-0) include the following structural units, and structural units in which a methyl group corresponding to R°* in the structural unit (a4-0) is substituted with a hydrogen in the following structural units:
    [0073] [0073] RA41 H2 VS
    [0074] [0074] Examples of the saturated hydrocarbon group in R** include a chain hydrocarbon group and a monocyclic or polycyclic alicyclic hydrocarbon group, and the groups formed by combining these groups.
    [0075] [0075] Examples of the chain hydrocarbon group include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group. , a pentadecyl group, a hexadecyl group, a heptadecyl group and an octadecyl group.
    [0076] [0076] Examples of the substituent belonging to R°* include at least one selected from the group consisting of a halogen atom and a group represented by the formula (a-g3). Examples of halogen atom include fluorine atom, chlorine atom, bromine atom and iodine atom, and fluorine atom is preferred: % ——X2a43—pa45 (ag 3) where, in the formula (a-g3), X represents an oxygen atom, a carbonyl group, *-O-CO- or *-CO-O-, A: represents a saturated hydrocarbon group having 1 to 17 carbon atoms optionally having a halogen atom, and * represents a binding site at R2*2.
    [0077] [0077] Examples of the saturated hydrocarbon group in A include alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, pentadecyl group, hexadecyl group, heptadecyl group and octadecyl group; monocyclic alicyclic hydrocarbon groups such as cyclopentyl group, cyclohexyl group, cycloheptyl group and cyclooctyl group; and polycyclic alicyclic hydrocarbon groups such as decahydronaphthyl group, adamantyl group, norbornyl group and the following groups (* represents a bonding site).
    [0078] [0078] R°*2 is preferably a saturated hydrocarbon group optionally having a halogen atom, and more preferably an alkyl group having a halogen atom and/or a saturated hydrocarbon group having a group represented by the formula ( a-g3).
    [0079] When R°* is a saturated hydrocarbon group having the group represented by formula (a-g3), R°° is more preferably a group represented by formula (a-g2): + —A216_x244__pa47 (a- g2) where, in the formula (a-g2), A°*° represents a divalent saturated hydrocarbon group having 1 to 17 carbon atoms optionally having a halogen atom, X21* represents **-O-CO- or * *-CO-O- (** represents a binding site at A°*°), A represents a saturated hydrocarbon group having 1 to 17 carbon atoms optionally having a halogen atom, the total number of carbon atoms of A°°, A and X°** is 18 or less, and at least one of A°* and A°* has at least one halogen atom, and * represents a bonding site to a carbonyl group.
    [0080] [0080] The number of carbon atoms of the saturated hydrocarbon group of A3' is preferably 1 to 6, and more preferably 1 to 3.
    [0081] [0081] The preferred structure of the group represented by the formula (a-g2) is the following structure (* represents a bonding site to a carbonyl group).
    [0082] [0082] Examples of alkanediyl group in A°* include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane- 1,5-diyl and a hexane-1,6-diyl group; and branched alkanediyl groups such as propane-1,2-diyl group, butane-1,3-diyl group, 2-methylpropane-1,2-diyl group, 1-methylbutane-1,4-diyl group and a 2-methylbutane-1,4-diyl group. Examples of the substituent in the alkanediyl group represented by A°# include a hydroxy group and an alkoxy group having 1 to 6 carbon atoms. A*! is preferably an alkanediyl group having 1 to 4 carbon atoms, more preferably an alkanediyl group having 2 to 4 carbon atoms, and more preferably an ethylene group.
    [0083] [0083] Examples of the divalent saturated hydrocarbon group represented by A A23 and A * in the group represented by formula (a-g1) include a linear or branched alkanediyl group and a monocyclic divalent alicyclic saturated hydrocarbon group, and divalent saturated hydrocarbon groups formed by combining an alkanediyl group and a saturated hydrocarbon group divalent alicyclic. Specific examples thereof include methylene group, ethylene group, propane-1,3-diyl group, propane-1,2-diyl group, butane-1,4-diyl group, 1- methylpropane-1,3-diyl, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group and the like. Examples of the substituent of the divalent saturated hydrocarbon group represented by A22, A and A include a hydroxy group and an alkoxy group having 1 to 6 carbon atoms. s is preferably 0.
    [0084] In the group represented by the formula (a-g1), examples of the group in which X** is -O-, -CO-, -CO-O- or -O-CO- include the following groups. In the following examples, * and ** each represent a binding site, and ** represents a binding site at -O-CO-R°*,
    [0085] [0085] Examples of the structural unit represented by the formula (a4-1) include the following structural units, and the structural units in which a methyl group corresponding to A°* in the structural unit represented by the formula (a4- 1) in the following structural units is substituted with a hydrogen atom. CHs CHa CHa CH» CHs CHs tl el vr Pl Le Le
    [0086] [0086] Hs Hz Hz Hz Hs Hz tt “jen er: ers er: er:
    [0087] [0087] Examples of the structural unit represented by the formula (a4-1) include a structural unit represented by the formula (a4-2) and a structural unit represented by the formula (a4-3): Ha RS 7 O (a4-2) L44 O7 do where, in the formula (a4-2), R® represents a hydrogen atom or a methyl group,
    [0088] [0088] Examples of the alkanediyl group having 1 to 6 L*% carbon atoms include the same groups as mentioned for
    [0089] The structural unit represented by the formula (a4-2) includes, for example, the structural units represented by the formula (a4-1-1) to the formula (a4-1-11). A structural unit in which a methyl group corresponding to RË in the structural unit (a4-2) is substituted with a hydrogen atom is also exemplified as a structural unit represented by (a4-2):
    [0090] [0090] Ha OR"
    [0091] [0091] Examples of the alkanediyl group in L° include those which are the same as those mentioned in the alkanediyl group of A**,
    [0092] The divalent saturated hydrocarbon group optionally having a fluorine atom in A is preferably a divalent chain saturated hydrocarbon group optionally having a fluorine atom and a divalent saturated alicyclic hydrocarbon group optionally having a fluorine atom, and more preferably a perfluoroalkanediyl group.
    [0093] [0093]
    [0094] [0094] In the formula (a4-3), L° is preferably an ethylene group. The divalent saturated hydrocarbon group of Af is preferably a group including a divalent chain saturated hydrocarbon group having 1 to 6 carbon atoms and a divalent alicyclic saturated hydrocarbon group having 3 to 12 carbon atoms, and more preferably a divalent chain saturated hydrocarbon group having 2 to 3 carbon atoms. The saturated hydrocarbon group of A* is preferably a group including a chain saturated hydrocarbon group having 3 to 12 carbon atoms and an alicyclic saturated hydrocarbon group having 3 to 12 carbon atoms, and more preferably a group including a hydrocarbon group saturated hydrocarbon group having 3 to 10 carbon atoms and an alicyclic saturated hydrocarbon group having 3 to 10 carbon atoms. Of these groups, Af!* is preferably a group including an alicyclic saturated hydrocarbon group having 3 to 12 carbon atoms, and more preferably a cyclopropylmethyl group, a cyclopentyl group, a cyclohexyl group, a norbornyl group and an adamantyl group.
    [0095] The structural unit represented by formula (a4-3) includes, for example, structural units represented by formula (a4-1"-1) to formula (a4-1'-11). structural unit in which a methyl group corresponding to R” in a structural unit (a4-3) is substituted with a hydrogen atom is also exemplified as a structural unit represented by (a4-3).
    [0096] It is also possible to cite by way of example, as structural unit (a4), a structural unit represented by the formula (a4-4):
    [0097] [0097] Examples of the saturated hydrocarbon group of R* include those which are the same as the saturated hydrocarbon group represented by R°*2, RP2 is preferably an alkyl group having 1 to 10 carbon atoms having a fluorine atom or an alicyclic saturated hydrocarbon group having 1 to 10 carbon atoms having a fluorine atom, more preferably an alkyl group having 1 to 10 carbon atoms having a fluorine atom, and more preferably an alkyl group having 1 to 6 atoms carbon having a fluorine atom.
    [0098] [0098]
    [0099] [0099] The structural unit represented by the formula (a4-4) includes, for example, the following structural units and the structural units in which a methyl group corresponding to R* in the structural unit (a4-4) is substituted with a hydrogen atom in the structural units represented by the following formulas.
    [0100] [0100] When the resin (A) includes the structural unit (a4), the content is preferably 1 to 20 mol%, more preferably 2 to 15 mol%, and more preferably 3 to 10 mol%, on the basis of all the structural units of the resin (A).
    [0101] <Structural unit (a5)> Examples of the non-leaving hydrocarbon group belonging to the structural unit (a5) include groups having a linear, branched or cyclic hydrocarbon group. Of these, the structural unit (a5) is preferably a group having an alicyclic hydrocarbon group. The structural unit (a5) includes, for example, a structural unit represented by the formula (a5-1):
    [0102] [0102] The alicyclic hydrocarbon group in R° can be monocyclic or polycyclic. The monocyclic alicyclic hydrocarbon group includes, for example, cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclohexyl group. The polycyclic alicyclic hydrocarbon group includes, for example, an adamantyl group and a norbornyl group.
    [0103] [0103] Examples of the divalent saturated hydrocarbon group in L” include a divalent chain saturated hydrocarbon group and a divalent alicyclic saturated hydrocarbon group, and a divalent chain saturated hydrocarbon group is preferred.
    [0104] The group in which -CHz- included in the divalent saturated hydrocarbon group represented by L°° is replaced by -O- or -CO- includes, for example, the groups represented by the formula (L1-1) at formula (L1-4). In the following formulas, * and ** each represent a binding site, and * represents a binding site to an oxygen atom.
    [0105] [0105] Lt is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, and more preferably a methylene group or an ethylene group.
    [0106] The group represented by the formula (L1-1) includes, for example, the following divalent groups. + xx #2 xx 3 xx #04 x Aon, * 18 x H CHs Hs AAA ASS HAS
    [0107] The group represented by formula (L1-2) includes, for example, the following divalent groups. kk Ho kk Ho Xx OA X me N DD, 3 3 , A Aho” so" Aho , tre”
    [0108] The group represented by the formula (L1-3) includes, for example, the following divalent groups. Hs 9 2 Ak re DNA DAN, A O Hs Ö
    [0109] The group represented by the formula (L1-4) includes, for example, the following divalent groups. î À ek À" SI en NY 0” „SIT CN A FH * HA OM DISS DS
    [0110] [0110] L°° is preferably a single bond or a group represented by the formula (L1-1).
    [0111] [0111] Examples of the structural unit (a5-1) include the following structural units and the structural units in which a methyl group corresponding to R° in the structural unit (a5-1) is substituted with a hydrogen atom in the following structural units.
    [0112] [0112]
    [0113] <Structural unit (II)> The resin (A) may further include a structural unit which is decomposed by exposure to radiation to generate an acid (hereinafter sometimes referred to as "structural unit (IT)"). Specific examples of the structural unit (IT) include the structural units mentioned in JP 2016-79235 A, and a structural unit having a sulfonate group or a carboxylate group and an organic cation in a side chain or a structural unit having a group sulfonio and an organic anion in a side chain are preferred.
    [0114] [0114] The structural unit having a sulfonate group or a carboxylate group and an organic cation in a side chain is preferably a structural unit represented by the formula (II-2-A"):
    [0115] [0115] Examples of the halogen atom represented by RS include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
    [0116] [0116] Examples of the divalent saturated hydrocarbon group having 1 to 18 carbon atoms represented by X" include a linear or branched alkanediyl group, a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, or a combination thereof.
    [0117] [0117] Those in which -CHz- included in the saturated hydrocarbon group are replaced by -O-, -S- or -CO- include, for example, divalent groups represented by formula (X1) to formula (X53) . Before replacing -CHz- included in the saturated hydrocarbon group with -O-, -S- or -CO-, the number of carbon atoms is 17 or less. In the following formulas, * and ** represent a binding site, and * represents an A' binding site.
    [0118] [0118] X represents a divalent saturated hydrocarbon group having 1 to 16 carbon atoms. X* represents a divalent saturated hydrocarbon group having 1 to 15 carbon atoms. X° represents a divalent saturated hydrocarbon group having 1 to 13 carbon atoms. X° represents a divalent saturated hydrocarbon group having 1 to 14 carbon atoms. X' represents a trivalent saturated hydrocarbon group having 1 to 14 carbon atoms. X® represents a divalent saturated hydrocarbon group having 1 to 13 carbon atoms.
    [0119] [0119] Examples of the organic cation represented by ZA + include organic onium cation, organic sulfonium cation, organic iodonium cation, organic ammonium cation, benzothiazolium cation and organic phosphonium cation. Among these organic cations, an organic sulfonium cation and an organic iodonium cation are preferred, and an arylsulfonium cation is more preferred. Specific examples thereof include a cation represented by any one of the formula (b2-1) to the above-mentioned formula (b2-4) (hereinafter sometimes referred to as "cation (b2-1)" according to formula number).
    [0120] The structural unit represented by the formula (II-2-A") is preferably a structural unit represented by the formula (II-2-A): RIIS
    [0121] [0121] Examples of the perfluoroalkyl group having 1 to 6 carbon atoms represented by R!2 RI Q and Q include those which are the same as the perfluoroalkyl group having 1 to 6 carbon atoms represented by Q” mentioned later.
    [0122] The structural unit represented by formula (II-2-A) is preferably a structural unit represented by formula (II-2-A-1):
    [0123] [0123] Examples of the saturated hydrocarbon group having 1 to 12 carbon atoms represented by RS include linear or branched alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec -butyl, tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group and dodecyl group.
    [0124] [0124] The structural unit represented by the formula (II-2-A-1) is preferably a structural unit represented by the formula (II-2-A-2):
    [0125] [0125] The structural unit represented by the formula (II-2-A") includes, for example, the following structural units, the structural units in which a group corresponding to the methyl group of RIB is substituted by an alkyl group having 1 to 6 carbon atoms optionally having a hydrogen atom, a halogen atom (for example, a fluorine atom) or a halogen atom (for example, a trifluoromethyl group, etc.) and the structural units mentioned in WO 2012/050015 A. ZA” represents an organic cation.
    [0126] [0126]
    [0127] [0127] Examples of the structural unit including a cation in the formula (II-1-1) include the following structural units, the structural units in which a group corresponding to the methyl group of R"* is substituted by an atom of hydrogen, a halogen atom (for example, a fluorine atom) or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom (for example, a trifluoromethyl group etc.).
    [0128] [0128] Examples of the organic anion represented by A include a sulfonic acid anion, a sulfonylimide anion, a sulfonyl methide anion and a carboxylic acid anion. The organic anion represented by A is preferably a sulfonic acid anion, and examples of the sulfonic acid anion include those which are the same as an anion represented by the above-mentioned formula (B1).
    [0129] [0129] Examples of the sulfonylimide anion represented by A include the following. F2 frs FafC -CF3 F 023 CFa 028-CF2 028-CF2 0.8-CF, o,s L LL 47 O2S-CF3 O2S-CF2 O2S-CF2 ot F, of, CF, FÈ-C-CF; F2
    [0130] [0130] Examples of the sulfonyl methide anion include the following.
    [0131] [0131] Examples of the carboxylic acid anion include the following. Ae and ie A ef Bf Oe CHs H
    [0132] [0132] Examples of the structural unit represented by formula (II-1-1) include structural units represented by the following formulas. Hz Hz Hz in Tet tot
    [0133] [0133] When the structural unit (IT) is included in the resin (A), the content of the structural unit (IT) is preferably 1 to 20 mol%, more preferably 2 to 15 mol®%, and more preferably 3 to 10 mol%, based on all structural units of resin (A).
    [0134] The resin (A) may include structural units other than the aforementioned structural units, and examples of the structural units include the structural units well known in the art.
    [0135] The resin (A) is preferably a resin composed of a structural unit (a1) and a structural unit (s), that is to say a copolymer of a monomer (al) and d a monomer(s).
    [0136] The respective structural units constituting the resin (A) may be used singly, or two or more structural units may be used in combination. By using a monomer from which these structural units are derived, it is possible to produce these structural units by a known polymerization process (eg, a radical polymerization process). The content of respective structural units included in the resin (A) can be adjusted depending on the amount of monomer used in the polymerization.
    [0137] <Resin other than Resin (A)> The resist composition according to some embodiments of the present invention may include the resin other than Resin (A).
    [0138] The resin (X) is preferably a resin including a structural unit (a4), in particular.
    [0139] The content of the resin (A) in the resist composition is preferably 80% by mass or more and 99% by mass or less, and more preferably 90% by mass or more and 99% by mass or less. , based on the solid component of the resist composition. When including resins other than resin (A), the total content of resin (A) and resins other than resin (A) is preferably 80% by mass or more and 99% by mass or less, and more preferably 90 mass% or more and 99 mass% or less, based on the solid component of the resist composition. The solid component of the resist composition and the content of the resin can be measured by a known analytical means such as liquid chromatography or gas chromatography.
    [0140] [0140] …<Acid Generator (B)> A nonionic or ionic acid generator can be used as acid generator (B). Examples of nonionic acid generator include sulfonate esters (eg, 2-nitrobenzyl ester, aromatic sulfonate, oxime sulfonate, N-sulfonyloxyimide, sulfonyloxyketone, diazonaphthoquinone 4-sulfonate), sulfones (eg, disulfone , ketosulphone, sulfonyldiazomethane) and the like. Typical examples of the ionic acid generator include onium salts containing an onium cation (eg, diazonium salt, phosphonium salt, sulfonium salt, iodonium salt). Examples of the onium salt anion include sulfonic acid anion, sulfonylimide anion, sulfonylmethide anion and the like.
    [0141] [0141] Specific examples of the acid generator (B) include compounds generating acid upon exposure to radiation mentioned in JP 63-26653 A, JP 55-164824 A, JP 62-69263 A, JP 63-146038 A , JP 63-163452 A, JP 62-153853 A, JP 63-146029 A, US Patent No.
    [0142] The acid generator (B) is preferably an acid generator containing fluorine, and more preferably a salt represented by the formula (B1) (hereinafter sometimes referred to as “acid generator (B1) ”): Qh + -0.S [61 21 OS AS, (B) des where, in the formula (B1), Q% and Q° each independently represent a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon, LP represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, -CHz- included in the divalent saturated hydrocarbon group may be replaced by -O- or -CO-, and a hydrogen atom included in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group, Y represents a methyl group which may have a substituent or an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and -CH>- included in the hydrocarbon group alicyclic can be replaced by -O-, -S(O)2- or -CO-, and Z1* represents an organic cation.
    [0143] [0143] Examples of the perfluoroalkyl group represented by Q1 and QP2 include trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluorobutyl group, perfluorosec-butyl group, perfluorotert-butyl group, perfluoropentyl group. and a perfluorohexyl group.
    [0144] [0144] Examples of divalent saturated hydrocarbon group in LP include a linear alkanediyl group, a branched alkanediyl group, and a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, or the divalent saturated hydrocarbon group may be a group formed by combining two or more of these groups in combination.
    [0145] [0145]
    [0146] [0146] A N b3 *% OS # O —* No A; DS, ba T * DS, 66” > b7
    [0147] [0147] In the groups represented by the formula (b1-1) to the formula (b1-3), when -CHz- included in the saturated hydrocarbon group is replaced by -O- or -CO-, the number of atoms of carbon before replacement is taken as the number of carbon atoms of the saturated hydrocarbon group.
    [0148] The group in which -CHz- included in the divalent saturated hydrocarbon group represented by L! is replaced by -O- or -CO- is preferably a group represented by formula (b1-1) or formula (b1-3).
    [0149] [0149] Examples of the group represented by the formula (b1-3) include the groups represented by the formula (b1-9) to the formula (b1-11). ARS AO ARE og
    [0150] [0150] In groups represented by formula (b1-9) to formula (b1-11), when a hydrogen atom included in the saturated hydrocarbon group is substituted with an alkylcarbonyloxy group, the number of carbon atoms before the substitution is taken as the number of carbon atoms of the saturated hydrocarbon group. Examples of the alkylcarbonyloxy group include acetyloxy group, propionyloxy group, butyryloxy group, cyclohexylcarbonyloxy group, adamantylcarbonyloxy group and the like.
    [0151] [0151] Examples of the group represented by the formula (b1-4) include the following: O O 0 O O CH; * and ** represent a bond, and * represents a bond to Y.
    [0152] [0152] Examples of the group represented by the formula (b1-5) include the following: A Aten A An A
    [0153] [0153] Examples of the group represented by the formula (b1-6) include the following: 3 3 3 Q 0 0 OQ = Ate “other At Jr} ST where, * and ** represent a bond, and * represents a bond to Y.
    [0154] [0154] Examples of the group represented by the formula (b1-7) include the following: Hs Q ae í
    [0155] [0155] Examples of the group represented by the formula (b1-8) include the following:
    [0156] [0156] Examples of the group represented by the formula (b1-2) include the following:
    [0157] [0157] Examples of the group represented by the formula (b1-9) include the following:
    [0158] [0158] Examples of the group represented by the formula (b1-10) include the following: © AAA | © O Kk Hs ak Hz xx se sk ak xx 2 x AO weak H ** ak H Hs
    [0159] [0159] Examples of the group represented by the formula (b1-11) include the following: Hz ANA NS robot, MA AL, A, A, Ô ' dek ok û FFXF © FFF HR F CF3 F CFa £ N°0 % JOH From
    [0160] [0160] Examples of the alicyclic hydrocarbon group represented by Y include groups represented by formula (Y1) to formula (Y11) and by formula (Y36) to formula (Y38).
    [0161] [0161] Examples of the substituent of the methyl group represented by Y include a halogen atom, a hydroxy group, an alicyclic hydrocarbon group having 3 to 16 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, an glycidyloxy, a -(CHz);,-CO-OR®* group or a -(CH2);a-O-CO-RP! (where RP represents an alkyl group having 1 to 16 carbon atoms, an alicyclic hydrocarbon group having 3 to 16 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a group obtained by combining these groups, and -CH>- included in an alkyl group and the alicyclic hydrocarbon group may be replaced by -O-, -SOz- or -CO-, a hydrogen atom included in the alkyl group, the alicyclic hydrocarbon group and the aromatic hydrocarbon group may be substituted by a hydroxy group or a fluorine atom, and j represents an integer from 0 to 4).
    [0162] [0162] Examples of halogen atom include fluorine atom, chlorine atom, bromine atom and iodine atom. Examples of the alicyclic hydrocarbon group include cyclopentyl group, cyclohexyl group, methylcyclohexyl group, dimethylcyclohexyl group, cycloheptyl group, cyclooctyl group, norbornyl group, adamantyl group and the like. The alicyclic hydrocarbon group may have a chain hydrocarbon group, and examples of these include a methylcyclohexyl group, a dimethylcyclohexyl group and the like. The number of carbon atoms of the alicyclic hydrocarbon group is preferably 3 to 12, and more preferably 3 to 10. Examples of the aromatic hydrocarbon group include aryl groups such as phenyl group, naphthyl group, anthryl group , a biphenyl group and a phenanthryl group. The aromatic hydrocarbon group may have a chain hydrocarbon group or an alicyclic hydrocarbon group, and examples thereof include an aromatic hydrocarbon group which has a chain hydrocarbon group having 1 to 18 carbon atoms (a tolyl group, a xylyl, cumenyl group, mesityl group, p-methylphenyl group, p-ethylphenyl group, p-tert-butylphenyl group,
    [0163] [0163] Examples of Y include the following. A X Ar Def * Oo oO oP oF Io 07 07 (1100) Vion) * * * x x ( (Y102) (Y103) (Y104) , (105) (1106) © © Be A Ur A Hs, CH po
    [0164] [0164] Y is preferably an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, more preferably an alicyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent, more preferably a hydrocarbon group alicyclic having 3 to 18 carbon atoms which may have a substituent, more preferably an adamantyl group which may have a substituent, and -CHz- constituting the alicyclic hydrocarbon group or the adamantyl group may be replaced by -CO-, -S (O)2- or -CO-. Specifically, Y is preferably an adamantyl group, a hydroxyadamantyl group, an oxoadamantyl group or groups represented by formula (Y42) and formula (Y100) to formula (Y114).
    [0165] [0165] The anion in the salt represented by formula (B1) is preferably an anion represented by formula (B1-A-1) to formula (B1-A-59) [hereinafter sometimes referred to as "anion (B1-A-1)" according to the number of the formula], and more preferably an anion represented by any one of the formula (B1-A-1) to the formula (B1-A-4), the formula (B1-A-9), formula (B1-A- 10), formula (B1-A-24) to formula (B1-A-33), formula (B1-A- 36) to formula (B1-A-40) and formula (B1-A-47) to formula (B1-A-59).
    [0166] [0166] OH 0 ao Q»2 on b1 b2 Qb! Qb WHERE QU 0 _ O - Oo - Oo 048 SL A41 os TT LA 038 SL Adt 3 Sr Ö y 9 (B1-A-1) (B1-A-2) (B1-A-3) Qb Qb2 Qb Qb Ri2 ao Qb2 KO Bau Be RO
    [0168] [0168] O
    [0169] [0169] O4 O1 0 RS . Re 1 2 O 6 R So Ad Al FM LAG R RI 035 L TT © O 0 aL 7 D LA41 (B1-A-30) (B1-A-31) os” O (B1-A-32) O Te © ° 1 to 0 R 9 O Ve Ö _ Os, A44 - LA41 - LAHM 0:5 L 0:57 “od os] 07 So O Q F Q F (B1-A-33) F (B1-A-34) (B1-A-35) F
    [0170] [0170]
    [0171] [0171] O. O Re, A From To Mt From 07% 67% 9 Ò
    [0172] [0172]
    [0173] [0173] R to RU each independently represent, for example, an alkyl group having 1 to 4 carbon atoms, and preferably a methyl group or an ethyl group. R® is, for example, a chain hydrocarbon group having 1 to 12 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 5 to 12 carbon atoms or a group formed by combining these groups, and more preferably a methyl group, an ethyl group, a cyclohexyl group or an adamantyl group. LA is a single bond or an alkanediyl group having 1 to 4 carbon atoms. Q®* and QP2 are the same as those defined above.
    [0174] [0174] The anion in the salt represented by the formula (B1) preferably includes anions represented by the formula (B1a-1) to the formula (B1a-38).
    [0175] [0175]
    [0176] [0176] Me A Me XH Der 9 OO Ô O — F RF _ F 035 O3S O3 X (Bla-23) (Bla-24) (Bla-25) AA ROS: odf he 041% 04-10 — FRF _ F _ F (075) O3 O3
    [0177] Of these, an anion represented by any one of formula (B1a-1) to formula (B1a-3) and formula (B1a-7) to formula (B1a-16), formula (B1a-18), formula (B1a-19) and formula (B1a-22) to formula (B1a-38) is preferred.
    [0178] [0178] Examples of organic cation of Z1* include organic onium cation, organic sulfonium cation, organic iodonium cation, organic ammonium cation, benzothiazolium cation and organic phosphonium cation. Of these, an organic sulfonium cation and an organic iodonium cation are preferred, and an arylsulfonium cation is more preferred. Specific examples thereof include a cation represented by any one of formula (b2-1) to formula (b2-4) (hereinafter sometimes referred to as "(b2-1)cation" depending on the number of the formula).
    [0102] [0102] (RB13) 2 (RE17) 2 RB4 (RD) ma R® 9 © 15 © RbS-6+ Oo D Locale 1 5 )a2 S+ R6 WJ | ado 1 " GG Q (re jn A Sa (b2-1) (b2-2) (b2-3) (RP 14) 2 1 u2 1/(u2+1) (b2-4) In the formula (b2- 1) in the formula (b2-4), RP* to RP each independently represent a chain hydrocarbon group having 1 to 30 carbon atoms, an alicyclic hydrocarbon group having 3 to 36 carbon atoms or an aromatic hydrocarbon group having 6 to 36 carbon atoms, a hydrogen atom included in the chain hydrocarbon group may be substituted with a hydroxy group, an alkoxy group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 3 to 12 carbon atoms or a group aromatic hydrocarbon having 6 to 18 carbon atoms, a hydrogen atom included in the alicyclic hydrocarbon group may be substituted with a halogen atom, an aliphatic hydrocarbon group having 1 to 18 carbon atoms, an alkylcarbonyl group having 2 to 4 carbon atoms or a glycidyloxy group, and a hydrogen atom included in the aromatic hydrocarbon group may be s substituted with a halogen atom, a hydroxy group, an aliphatic hydrocarbon group having 1 to 18 carbon atoms, an alkyl fluoride group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, RP * and RP5 can be bonded to each other to form a ring with the sulfur atoms to which RP* and RP° are bonded, and -CHz- included in the ring can be replaced by -O-, -S- or -CO-, RP” and R® each independently represents a halogen atom, a hydroxy group, an aliphatic hydrocarbon group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms,
    [0179] The aliphatic hydrocarbon group represents a chain hydrocarbon group and an alicyclic hydrocarbon group.
    [0180] [0180] Examples of an alicyclic hydrocarbon group in which a hydrogen atom is substituted with an aliphatic hydrocarbon group include methylcyclohexyl group, dimethylcyclohexyl group, 2-methyladamantan-2-yl group, 2-ethyladamantan-2- yl, 2-isopropyladamantan-2-yl group, methylnorbornyl group, isobornyl group and the like. In the alicyclic hydrocarbon group in which a hydrogen atom is substituted with an aliphatic hydrocarbon group, the total number of carbon atoms of the alicyclic hydrocarbon group and the aliphatic hydrocarbon group is preferably 20 or less.
    [0181] [0181] Examples of the aromatic hydrocarbon group include aryl groups such as phenyl group, biphenyl group, naphthyl group and phenanthryl group. The aromatic hydrocarbon group may have a chain hydrocarbon group or an alicyclic hydrocarbon group, and examples thereof include an aromatic hydrocarbon group having a chain hydrocarbon group (a tolyl group, a xylyl group, a cumenyl group, a mesityl group, p-methylphenyl group, p-ethylphenyl group, p-tert-butylphenyl group, 2,6-diethylphenyl group, 2-methyl-6-ethylphenyl group etc.), and an aromatic hydrocarbon group having a hydrocarbon group alicyclic (a p-cyclohexylphenyl group, a p-adamantylphenyl group etc.). When the aromatic hydrocarbon group has a chain hydrocarbon group or the 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 preferable.
    [0182] Examples of the alkoxy group include methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, decyloxy group and dodecyloxy group.
    [0183] [0183] The ring formed by linking RP* and RP5 together, with the sulfur atoms to which RP and RP are linked, can be a monocyclic, polycyclic, aromatic, non-aromatic, saturated or unsaturated ring. This ring includes a ring having 3 to 18 carbon atoms and is preferably a ring having 4 to 18 carbon atoms. The sulfur atom-containing ring includes a 3 to 12 membered ring and is preferably a 3 to 7 membered ring and includes, for example, the following rings and the like. * represents a bond. THE TO TO TO TO LENS OPGAAN O O
    [0184] [0184] The cycle formed by combining RP and RP!° together can be a monocyclic, polycyclic, aromatic, non-aromatic, saturated or unsaturated ring. This ring includes a 3 to 12 membered ring and is preferably a 3 to 7 membered ring. The ring includes, for example, a thiolan-1-ium ring (a tetrahydrothiophenium ring), a thian-1-ium ring, a 1,4-oxathian-4-ium ring and the like.
    [0185] Among the cation (b2-1) to the cation (b2-4), a cation (b2-1) is preferred. Examples of cation (b2-1) include the following cations. 6 CaH5 © Ò CgH43 CaH47 (b2-c-1) (b2-c-2) (b2-c-3) (b2-c-4) (b2-c-5) (b2-c-6) | (b2-C-7) (b2-c-8) © 6 Hs -C4H9 -C4H9 + + + CH Ç > 2 Of “© of Ee Off OS H a b2-c-12 tC,H, (b2-c -14) (b2-c-9) (b2-c-10) 22-11) 02-012) (b2-0-13)
    [0186] [0186]
    [0187] [0187] Examples of cation (b2-2) include the following cations. + + + DK) + TX )— > TX y— F4 (b2-c-28) (b2-c-29) (b2-c-30) (b2-c-50)
    [0188] [0188] Examples of cation (b2-3) include the following cations.
    [0189] [0189] Examples of cation (b2-4) include the following cations. Hz (2 (2 (2 (2 OO AO A Oe A > WD vaa (b2-c-36) (b2-c-37) (b2-c-38) Hs Hs Hs Hs QQ 4 Q OOo OO ZOO JOO Oo CG ww ® (b2-c-39) (b2-c-40) H3 (b2-c-41) Ha (b2-c-42) t-CaHo t-CaHo t-CaH9 t-C4He (2 (4 ( 2 @ AOV Kd sper OO SS re (b2-c-43) U) (b2-c-44) 97 (b2-c-45) tad, (b2-c-46) 300 (b2-c-54)
    [0190] [0190] The acid generator (B) is a combination of the aforementioned anion and the aforementioned organic cation, and these may be optionally combined. The acid generator (B) preferably includes a combination of an anion represented by any one of formula (B1a-1) to formula (B1a-3), formula (B1a-7) to formula (Bla-16), formula (B1a-18), formula (B1a-19) and from formula (B1a-22) to formula (B1a-38) with a cation (b2-1), a cation (b2-3), a cation (b2-4).
    [0191] The acid generator (B) preferably includes those represented by formula (B1-1) to formula (B1-56). Among these acid generators, those containing an arylsulfonium cation are preferred, and those represented by formula (B1-1) to formula (B1-3), formula (B1-5) to formula (B1-7) , formula (B1-11) to formula (B1-14), formula (B1-20) to formula (B1-26), formula (B1-29) and formula (B1-31) to formula (B1-56) are particularly preferred.
    [0192] [0192] € FK JF OO FK LF + ® O ae * 8 (B1-13) (B1-14) (B1-15) | © On . Ö° 5 (B1-17) U) (B1-18) (B1-16)
    [0193] [0193] dx 2 03 © _ BF _ BF (81-22) (SS SST Ay ST Ô (B1-23) (B1-24) O © OO FF: © CELL On 7 5 Lane (81-25) 3 ( B1-26) 81.27) ae On RO O8 AT OER ©. F FE, (81-28) 8129 5 F The (B1-30)
    [0194] [0194] | O. F LP Go a AT oe GT oock (B1-37) (B1-38) (B1-39) CO “© CA A ©) AX os” QO De XO Oh, +7 AA 7 A © (B1-40 ) Or ° Ô Vod Ô (B1-41) (B1-42)
    [0195] [0195]
    [0196] In the resist composition according to some embodiments of the present invention, the total content of the acid generator is preferably 1 part by mass or more and 45 parts by mass or less, more preferably 1 part by mass. mass or more and 40 parts by mass or less, and more preferably 3 parts by mass or more and 40 parts by mass or less, and more preferably 10 parts by mass or more and 40 parts by mass or less based on 100 parts by mass of the resin (A) mentioned below.
    [0197] [0197] <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, preferably 92% by mass or more and 99% by mass or less, and more preferably 94% by mass or more and 99% by mass or less. The content of the solvent (E) can be measured, for example, by a means of analysis known as liquid chromatography or gas chromatography.
    [0198] [0198] <Deactivating agent (C) ("Quencher (C)")> Examples of deactivating agent (C) include an organic compound containing basic nitrogen, and an acid-generating salt having a lower acidity. to that of an acid generated from an acid generator (B). When the resist composition includes the quenching agent, the content of the quenching agent (C) is preferably about 0.01 to 15% by weight, more preferably about 0.01 to 10% by weight. , more preferably about 0.1 to 5% by mass, and more preferably about 0.1 to 3% by mass, based on the amount of the solid component of the resist composition.
    [0199] [0199]
    [0200] [0200] Examples of the weak acid inner salt (D) include the following salts. _ 007 700C + 007 oo do D:0 O0 HO 040 007 oo” oo oo 007 007 0550 dd odio Br CI 007 oo oo 00 00° NO Hoo Ho Vo Go AG _ x _ AO oO De Es ER
    [0201] <Other components> The resist composition according to certain embodiments of the present invention may also include components other than the components mentioned above (hereinafter sometimes referred to as "other components (F)"), if necessary. . The other components (F) are not particularly limited and it is possible to use various additives known in the field of resists, for example sensitizers, dissolution inhibitors, surfactants, stabilizers and colorants.
    [0202] <Preparation of the resist composition> The resist composition according to some embodiments of the present invention can be prepared by mixing a compound (I), a resin (A) and a heat generator. acid (B), resins other than the resin (A) to be used, a solvent (E), a deactivating agent (C) and other components (F). The mixing order of these components is any order and it is not particularly limited. It is possible to select, as the temperature during mixing, an appropriate temperature of 10 to 40°C, depending on the kind of the resin, the solvent solubility (E) of the resin and the like. It is possible to choose, as mixing time, an appropriate time of 0.5 to 24 hours depending on the mixing temperature. The mixing means is not particularly limited and it is possible to use mixing with agitation.
    [0203] [0203] (Method for producing a resist pattern) The method for producing a resist pattern according to certain embodiments of the present invention includes: (1) a step of applying the resist composition according to certain embodiments of the present invention on a substrate, (2) a step of drying the resist composition applied to form a layer of composition, (3) a step of exposing the layer of composition, (4) a step of heating the exposed composition layer, and (5) a step of developing the heated composition layer.
    [0204] [0204] (Application) The resist composition according to some embodiments of the present invention is suitable as a resist composition for KrF excimer laser exposure, a resist composition for ArF excimer laser exposure, a electron beam (EB) exposure resist or UVE exposure resist composition, in particular an electron beam (EB) exposure resist composition or UVE exposure resist composition , and the resist composition is useful for fine processing of semiconductors.
    [0205] [0205] Certain embodiments of the present invention will be described more specifically by way of examples. The percentages and the parts expressing the contents or the amounts used in the examples are by weight unless otherwise indicated.
    [0206] [0206] The structures of the compounds were confirmed by measuring a molecular ion peak by mass spectrometry (liquid chromatography: Model 1100, manufactured by Agilent Technologies, Inc., mass spectrometry: Model LC/MSD, manufactured by Agilent Technologies , Inc.). The value of this molecular ion peak in the following examples is indicated by “MASS”.
    [0207] [0207] Resin Synthesis The compounds (monomers) used in the synthesis of a resin (A) are illustrated below. In the following, these compounds are referred to as “(a1-1-3) monomer” according to the formula number.
    [0208] Synthesis Example 1 [Synthesis of Resin A1] A monomer (a1-1-3) and a monomer (a1-2-6), a monomer (a2-1-3), a monomer ( a3-4-2) and a monomer (a1-4-2) as monomers, these monomers were mixed in a molar ratio of 20:35:3:15:27 [monomer (a1-1-3):monomer ( a1-2-6):monomer (a2-1-3):monomer (a3-4-2):monomer (a1-4-2)] and methyl isobutyl ketone was added in an amount of 1.5 times the total mass of all monomers. To the mixture thus obtained, azobisisobutyronitria and azobis(2,4-dimethylvaleronitrile) were added as initiators in the amount of 1.2 mol% and 3.6 mol% based on the molar number total of all monomers, followed by heating at 73°C for about 5 hours. To the polymerization reaction solution thus obtained, an aqueous solution of p-acid
    [0209] Synthesis Example 2 [Synthesis of Resin A2] A monomer (a1-1-3), a monomer (a1-2-6), a monomer (a2-1-3), a monomer ( a3-4-2) and a monomer (a1-4-13) as monomers, these monomers were mixed in a molar ratio of 20:35:3:15:27 [monomer (a1-1-3): monomer ( a1-2-6): monomer (a2-1-3): monomer (a3-4-2): monomer (a1-4-13)] and methyl isobutyl ketone was added in an amount of 1.5 times the total mass of all monomers. To the mixture thus obtained, azobisisobutyronitrile and azobis (2,4-dimethylvaleronitrile) were added as initiators in amounts of 1.2 mol% and 3.6 mol% based on the molar number total of all monomers, followed by heating at 73°C for about 5 hours. To the polymerization reaction solution thus obtained, an aqueous solution of p-toluenesulfonic acid (2.5% by weight) was added in an amount of 2.0 times the total mass of all monomers, thereby was followed by stirring for 12 hours and further isolation by separation. The organic layer thus obtained was poured into a large amount of n-heptane to precipitate a resin, followed by filtration and collection to obtain resin A2 having a weight-average molecular weight of about 5. 1 x 10° with a yield of 61%. This A2 resin has the following structural units.
    [0210] [0210] <Preparation of Resist Composition> As shown in Table 1, the following components were mixed and the resulting mixture was filtered through a fluororesin filter having a pore diameter of 0.2 µm to prepare resist compositions.
    [0211] [0211] Table 1 Composition of | Resin Gene- | Compound |PB agent/ resistor | (I) deactivation | PEB of acid on (C)
    [0212] [0212] <Resin> A1: Resin A1 <Acid generator (B)> B1-43: Salt represented by the formula (B1-43) (synthesized according to the examples of JP 2016-47815 A) K.K. AT PO
    [0213] [0213] (Evaluation of the exposure of a resist composition to an electron beam) Each silicon wafer, 6 inches (15.24 cm) in diameter, was treated with hexamethyldisilazane and then baked on a plate. direct heating at 90°C for 60 seconds. A resist composition was applied by centrifugal application (“spin coating”) on the silicon wafer so that the thickness of the layer of composition became 0.04 μm. The coated silicon wafer was then prebaked on the direct hot plate at the temperature shown in the "PB" column of Table 1 for 60 seconds to form a composition layer. Using a direct electron beam writing system ("ELS-F125 125 keV", manufactured by ELIONIX INC.), contact hole patterns (40 nm hole spacing / 17 nm) were written directly onto the composition layer formed on the wafer while the exposure dose was changed in steps.
    [0214] [0214] In the resist pattern obtained after development, the exposure dose at which the diameter of the formed holes reached 17 nm was considered as an effective sensitivity.
    [0215] [0215] <Evaluation of DC uniformity (CDU)> In the effective sensitivity, the diameter of holes of the resist pattern formed with a hole diameter of 17 nm was determined by measuring 24 times a same hole and the average of the measured values was taken as the average diameter of the hole. The standard deviation was determined under the conditions where the average diameter of 400 holes around the patterns formed with a hole diameter of 17 nm in the same wafer was considered as a population.
    [0216] [0216] table 2 | | Composition of resist__ |ŒQU | Comparing them with comparative composition 1, compositions 1 to 19 had a small standard deviation and a satisfactory evaluation of CD uniformity (CDU).
    [0217] [0217] Priority of Japanese Application No. 2020-037661 filed March 5, 2020, the contents of which are incorporated herein by reference, is claimed.
    权利要求:
    Claims (15)
    [1]
    1. A resist composition comprising a compound represented by formula (T), a resin having an acid labile group and an acid generator:
    O OH A (I) DL 1 A (R)m1 where, in the formula (I), R* represents a halogen atom or an alkyl fluoride group having 1 to 6 carbon atoms, m1 represents an integer of 1 to 5, and when m1 is 2 or more, a plurality of R* may be the same or different from each other.
    [2]
    2. The resist composition according to claim 1, wherein R* is a fluorine atom, an iodine atom or a trifluoromethyl group.
    [3]
    3. The resist composition according to claim 1, wherein m1 is an integer of 1 to 3.
    [4]
    4. The resist composition according to claim 1, wherein the R! comprises at least one iodine atom.
    [5]
    5. The resist composition according to claim 1, wherein the content of compound (I) is 0.001 to 20% by mass based on the solid content.
    [6]
    6. The resist composition according to claim 1, wherein the resin having an acid-labile group comprises at least one structural unit selected from the group consisting of a structural unit represented by formula (a1-1) and a structural unit structure represented by the formula (a1-2):
    Lt Ra4 Le Ras = | = | Lat La2 el Jom 1300, nt' (a1-1) (a1-2) where, in formula (a1-1) and formula (a1-2), Lt and L each independently represent -O- or *-O - (CH2)k1-CO-O-, and k1 represents an integer from 1 to 7, * represents a bonding site to -CO-, R°* and R® each independently represent a hydrogen atom, a halogen, or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, R°° and R 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 obtained by combining these groups, m1 represents an integer of 0 to 14, nl represents an integer of 0 to 10, and n1' represents an integer of 0 to 3.
    [7]
    7. The resist composition according to claim 6, wherein the resin having the acid-labile group includes the structural unit represented by the formula (a1-1).
    [8]
    8. The resist composition according to claim 6, wherein the resin having the acid-labile group includes the structural unit represented by the formula (a1-2).
    [9]
    9. The resist composition according to claim 6, wherein the resin having the acid labile group includes at least one structural unit represented by formula (a1-1) and includes at least one structural unit represented by formula (a1 -2).
    [10]
    10. The resist composition according to claim 1, wherein the resin having an acid labile group includes a structural unit represented by the formula (a2-A): a50
    HE A250A (a2-A); > OH (R°) where, in the formula (a2-A), R20 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms which may have a halogen atom, R ° 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 with 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, A20 represents a single bond or * -X®1_ (A82- x2°2) 5", and * represents a bonding site at carbon atoms to which -R°® is bonded, A represents an alkanediyl group having 1 to 6 carbon atoms, x°°1 and X252 each represent independently -O-, -CO-O- or -O-CO-, nb represents 0 or 1, and mb represents an integer from 0 to 4, and when mb is an integer from 2 or more, a plurali tee of R°** may be the same or different from each other.
    [11]
    11. The resist composition according to claim 1, wherein the acid generator includes a salt represented by the formula (B1): Qh! + -0.S 91 2* 038 | ALA (BIJ) des where, in the formula (B1), QP! and Q” each independently represents a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms, LP! represents a divalent saturated hydrocarbon group having 1 to 24 carbon atoms, -CH>- included in the divalent saturated hydrocarbon group may be replaced by -O- or -CO-, and a hydrogen atom included in the divalent saturated hydrocarbon group may be substituted with a fluorine atom or a hydroxy group, Y represents a methyl group which may have a substituent, or an alicyclic hydrocarbon group having 3 to 24 carbon atoms which may have a substituent, and -CH>- included in the alicyclic hydrocarbon group can be replaced by -O-, -S (O)>- or -CO-, and Z' represents an organic cation.
    [12]
    12. The resist composition of claim 1, further comprising a quenching agent such as an acid generating salt having a lower acidity than an acid generated from the acid generator.
    [13]
    13. The resist composition according to claim 1, wherein the compound represented by formula (I) includes compounds represented by the following formulas:
    COOH COOH COOH COOH COOH COOH DO. at C°” û CF4 CF3 F4 F F CF3 F (1-1) (1-2) (1-3) (1-4) (1-5) (1-6)
    COOH COOH COOH COOH COOH 5 F EN © ú 5 7 F F
    F F F F F
    M (1-7) (1-8) (1-9) (1-10) (1-11)
    COOH COOH COOH COOH COOH F 5 + F
    F F F 1 F F F (1-12) (1-13) (1-14) (1-15) (1-16)
    COOH COOH COOH COOH COOH COOH
    I I I I I T I I I ] I I I I I 1 1 I I I (1-17) (1-18) (1-19) (1-20) (1-21) (1-22)
    COOH COOH COOH COOH COOH COOH Sr OO A F © <q OO CF © M | F (1-23) (1-24) (1-25) (1-26) (1-27) (1-28)
    [14]
    14. The resist composition according to claim 1, wherein the compound represented by formula (I) includes compounds represented by the following formulas:
    GOH pe se ee EX gèoù Cool OOH Zoo Ë [ Ze SF ; LEDs &; © H XF À on Din Ca CA TC en 02) 9) 0) SO y an d-8) > 10 DOUR GOOR SG @ @ © Ô. 9 OL PON OP TON NN ga EE pa 028) 3-28)
    [15]
    15. A method for producing a resist pattern, which comprises: (1) a step of applying the resist composition according to claim 1 to a substrate, (2) a step of drying the applied resist composition to forming a composition layer, (3) a step of exposing the composition layer, (4) a step of heating the exposed composition layer, and (5) a step of developing the heated composition layer.
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