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    • 专利摘要:
    The present invention relates to a salt, a process for producing a salt and a deactivating agent as well as a resist composition comprising the same, said salt being represented by the formula (I) as defined in claim 1 wherein, in formula (I), R1 and R2 each represent a hydrocarbon group, and -CH2- included in the hydrocarbon group may be replaced by -O- or -CO-; R3, R4 and R5 each represent a halogen atom, an alkyl fluoride group or a hydrocarbon group, and CH2- included in the hydrocarbon group may be replaced by -O- or -CO-; m3 represents an integer of 0 to 2, and when m3 is 2, two R3s may be the same or different from each other; and m4 and m5 represent an integer of 0 to 5, and when m4 and / or m5 is / are 2 or more, a plurality of R4 and / or a plurality of R5 may be the same or different from each other.
    公开号:BE1027311B1
    申请号:E20205391
    申请日:2020-06-02
    公开日:2021-05-18
    发明作者:Katsuhiro Komuro；Yuki Takahashi；Koji Ichikawa
    申请人:Sumitomo Chemical Co；
    IPC主号:
    专利说明:

    [0001] The present invention relates to a salt, a "Quencher" quencher and a resist composition comprising the salt, a method for producing a resist pattern using the resist composition and a method for producing a salt. BACKGROUND OF THE INVENTION
    [0002] [0002] Patent document 1 mentions a method of synthesizing a salt having the following structural formula, and a resist composition including a salt having the following structural formula, a resin comprising a structural unit having a labile group in an acid medium , and an acid generator.
    [0003] [0003] Patent document 1: JP 2017-202993 A Description of the invention Problems to be solved by the invention
    [0004] An object of the present invention is to provide a salt capable of producing a resist pattern having a resolution better than that of a resist pattern formed from a resist composition comprising the aforementioned salt. Another object is to provide the salt derivative of the present invention in high yield. Means for resolving problems
    [0005] The present invention includes the following inventions.
    [1] [1] A salt represented by the formula (T): RT (Rò) ma R2
    [2] [2] A deactivation agent comprising a salt according to [11.
    [3] [3] A resist composition comprising the deactivating agent according to
    [2] [2], a resin including a structural unit having an acid labile group, and an acid generator.
    [4] [4] The resist composition according to [3], wherein the resin comprising a structural unit including an acid labile group includes at least one resin selected from the group consisting of a structural unit represented by formula (a1-1) and a structural unit represented by the formula (a1-2): ++ Rx Ie Je | © N S Am 9 | # 0 Le, LÉ NF CH het RT, Ch LS iaer {ait} {ai-2} where, in formula (a1-1) and formula (a1-2), L ° * and L ° * each independently represent -O- or * -O- (CH2) k1-CO-O-, k1 represents an integer from 1 to 7, and * represents a binding site to -CO-, R ° * and R °° each independently represent an hydrogen atom or a methyl group, R °° and R each independently represent an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 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 from 0 to 3.
    [5] [5] The resist composition according to [3] or [4], wherein the resin including a structural unit having an acid labile group includes a structural unit represented by the formula (a2-A):
    [6] [6] The resist composition according to any one of [3] to [5], wherein the acid generator includes a salt represented by formula (B1): + O, S [61 Z O3 Nes, (Bi) 1, where, in formula (B1),
    [7] [7] The resist composition according to any one of [3] to [6], further comprising an acid generating salt having an acidity lower than that of an acid generated by the acid generator.
    [8] [8] A method for producing a resist pattern, which comprises: (1) a step of applying the resist composition according to any one of [3] to [7] on a substrate, (2) a step of drying the applied composition to form a composition layer, (3) a step of exposing the composition layer, (4) a step of heating the exposed composition layer, and (5) a step of developing the composition. the heated composition layer.
    [9] [9] A process for producing a salt, which comprises: reacting a compound represented by formula (I-B) with a compound represented by formula (I-C) to produce a salt represented by formula (I):
    [0006] It is possible to produce a resist pattern with satisfactory resolution using a resist composition comprising a salt of the present invention. It is also possible to produce a salt of the present invention in a high yield.
    [0007] As used herein, the term "(meth) acrylate" means "at least one of: acrylate and methacrylate". Terms such as "(meth) acrylic acid" and "(meth) acryloyl" also have the same meaning.
    [0008] [0008] [Salt represented by formula (1)] The salt of the present invention relates to a salt represented by formula (I) (hereinafter sometimes referred to as "salt (I)>).
    [0009] Examples of the salt (T) include the salts represented by the following formulas.
    [0010] [0010] [Process for the synthesis of salt (I)] Salt (I) can be produced by mixing a salt represented by formula (IA) in the presence of a basic catalyst in a solvent: 1X 3 3 x 3 NN JB EN SE) BR} {Re RL Ae 2 DA SS Sogar _ | me le mm EL Le OS CP | | u Poe N> A Pa RE SRE NS mat RG y À IR irons A ne YR Ass (A background ng {T-A} {7} where all the symbols are identical to those defined above.
    [0011] The salt represented by formula (Ia) can be produced by reacting a compound represented by formula (Ib) with a compound represented by formula (Ic) in the presence of trifluoromethanesulfonic acid and trifluoroacetic anhydride in a solvent: RT (Rò) ms R2 1 Ri (Rm CF, SOzH ee S R2 _ OH - + $ O3S-CF3 N On Li, OO (R °) ma CF3 CF3 (R °) ms (Re) ma (Ib) (Ic) a) where all the symbols are identical to those defined above.
    [0012] In salt (I), the salt where R ° represents a methyl group can also be obtained by reacting a salt represented by formula (Id) in the presence of a basic catalyst in a solvent and passing the reaction product through an ion exchange resin (chlorine ion exchange resin), followed by treatment with a base and further by treatment with an aqueous solution of oxalic acid: OF (R °) ms RT (R5) n R R2 7 _ MA, 2We - zz —CF $ 3 O3S-CF; 8-9; (R °) ms y ON (RE) ma (Rô) ma ° (I-d) (T) where all the symbols are identical to those defined above. Examples of the base include sodium hydroxide, potassium hydroxide and the like.
    [0013] The salt represented by the formula (Id) can be obtained by reacting a compound represented by the formula (Ib) with a compound represented by the formula (Ie) in the presence = of trifluoromethanesulfonic acid and trifluoroacetic anhydride in a solvent: R (R) ms R2 0; CF-SO4H TC 5 | X a O Q Ca 0: S-CFz3 (R ma m COzMe oro er, y iom (Re) (I-b) (I-e) (I-a) where all the symbols are the same as defined above.
    [0014] <Deactivation agent, "Quencher"> The quencher of the present invention comprises a salt (I). The quencher can comprise one salt (I), or two or more salts (I).
    [0015] <Resist composition> The resist composition of the present invention includes a deactivating agent comprising a salt (I), a resin comprising a structural unit having an acid labile group (hereinafter sometimes referred to as "resin ( A) ”) and an acid generator (hereinafter sometimes referred to as“ acid generator (B) ”). The“ acid labile group ”means a group having a leaving group which is removed by contact with an acid. , thus forming a hydrophilic group (eg, a hydroxy group or a carboxy group) The resist composition of the present invention preferably comprises a solvent (hereinafter sometimes referred to as "solvent (E)").
    [0016] [0016] <Deactivating agent (or quencher) (C)> Examples of the deactivating agent (C) include a basic organic compound containing nitrogen and an acid generating salt having an acidity lower than that of an acid generated by an acid generator (B) mentioned later (excluding a salt represented by formula (I)). It is particularly preferable to contain an acid generating salt having an acidity lower than that of an acid generated by the acid generator (B) such as an internal salt of weak acid (hereinafter sometimes called "internal salt. of weak acid (D) ”).
    [0017] [0017] Examples of amines include 1-naphthylamine, 2-naphthylamine, aniline, diisopropylaniline, 2-, 3- or 4-methylaniline, 4-nitroaniline, N-methylaniline, N, N-dimethylaniline, diphenylamine, - hexylamine, heptylamine, octylamine, nonylamine, decylamine, dibutylamine, dipentylamine, dihexylamine, diheptylamine, dioctylamine, dinonylamine, didecylamine, triethylamine, trimethylamine, tripropylamine, tributylamine, tripentylamine, trihexylamine, triheptylamine, trioctylamine, trinonylamine, tridecylamine, methyldibutylamine, methyldipentylamine, methyldihexylamine, methyldildildihexylamine, methyldildildihexylamine, methyldildildihexylamine, methyldildildihexylamine, methyldildildoldihexylamine, methyldildildihexylamine, methyldildildicycloylamine, methyldildildihexylamine, methyldildildicycloylamine, laxyldildildildoldo-lamine , ethyldibutylamine, ethyldipentylamine, ethyldihexylamine, ethyldiheptylamine, ethyldioctylamine, ethyldinonylamine, ethyldidecylamine, la = dicyclohexylmethylamine, la = tris [2- (2- methoxyethoxy ) ethyl] amine, triisopropanolamine, ethylenediamine, tetramethylenediamine, hexamethylenediamine, 4,4 "-diamino-1,2-diphenylethane, 4,4" -diamino-3,3 "-dimethyldiphenylmethane, 4 , 4 "diamino-3,3'-diethyldiphenylmethane, 2,2'-methylenebisaniline, imidazole, 4-methylimidazole, pyridine, 4-methylpyridine, 1,2-di (2-pyridyl) ethane, 1,2-di (4-pyridyl) ethane, 1,2-di (2-pyridyl) ethene, 1,2-di (4-pyridyl) ethene, 1,3-di (4-pyridyl) propane, 1,2-di (4-pyridyloxy) ethane, di (2-pyridyl) ketone, 4,4 "-dipyridyl sulfide, 4,4'-dipyridyl disulfide, 2,2'- dipyridylamine, 2,2'-dipicolylamine, bipyridine and the like, preferably diisopropylaniline, and more preferably 2,6-diisopropylaniline.
    [0018] Examples of ammonium salt include tetramethylammonium hydroxide: = tetraisopropylammonium hydroxide, tetrabutylammonium hydroxide, tetrahexylammonium hydroxide, tetraoctylammonium hydroxide, phenyltrimethylammonium hydroxide , 3- (trifluoromethyl) phenyltrimethylammonium hydroxide, tetra-n-butylammonium salicylate and choline.
    [0019] The acidity in a salt generating an acid having an acidity lower than that of an acid generated from the acid generator (B) is indicated by the acid dissociation constant (pKa). generating an acid having an acidity lower than that of an acid generated from the acid generator (B), the acid dissociation constant of an acid generated from the salt usually responds to the following inequality: - -3 <pKa, preferably -1 <pKa <7, and more preferably 0 <pKa <5.
    [0020] Examples of the weak acid internal salt (D) include the following salts. gea ”IN, | ; DENT ”SON st = mu se Eee Den ASS al 5 IN, = + $ ST + at% Fast, LFP AS £ <> 8, DSN. dg Jr} 2 5007 zee goe PP zoo ”sos == 5 ==, qu = pe mn S = AS JS, 7 = S - =: =
    [0021] When the salt (I) and the quencher (C) are included as deactivating agent, a ratio between the content of salt (T) and that of the quencher (C) (mass ratio; salt (I ): quencher (C)) is generally between 1:99 and 99: 1, preferably between 2:98 and 98: 2, more preferably between 5:95 and 95: 5, more preferably between 10:90 and 90:10 and more preferably between 15:85 and 85:15.
    [0022] In the resist composition of the present invention, the salt (I) content is usually 0.001 to 20% by mass, preferably 0.005 to 15% by mass, and more preferably from 0.01 to 10. % by mass, based on the solids content of the resist composition. When the deactivating agent comprises the deactivating agent (C), the content of the deactivating agent (C) is preferably about 0.01 to 15% by weight, more preferably about 0.01 to 10%. by weight, more preferably from 0.01 to 5% by weight, and more preferably from 0.01 to 3% by weight, based on the solids content of the resist composition.
    [0023] <Resin A> The resin (A) comprises a structural unit having a labile group in an acid medium (hereinafter sometimes called "structural unit (a1)"). It is preferable that the resin (A) further includes a structural unit other than the 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 structural unit (a1) and structural unit (s) (for example, 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.
    [0024] [0024] <Structural Unit (a1)>
    [0025] Examples of the alkyl group for R ° *, R22 and R include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group and an octyl group and the like. .
    [0026] Examples of the hydrocarbon group for R °, R ° 2 and R ° include an alkyl group, an alicyclic hydrocarbon group, an aromatic hydrocarbon group and groups obtained by combining these groups.
    [0027] Examples of group (1) include the following groups.
    [0028] Specific examples of group (2) include the following groups. * represents a binding site.
    [0029] The monomer (a1) is preferably a monomer having a labile group in an acidic medium and an unsaturated ethylenic bond, and more preferably a (meth) acrylic monomer having a labile group in an acidic medium.
    [0030] Among the (meth) acrylic monomers having a labile group in an acid medium, 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.
    [0031] 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 called structural unit (a1-0)), a structural unit represented by formula (a1-1) (hereinafter sometimes called structural unit (a1-1)) or a structural unit represented by formula (a1-2) (hereinafter sometimes called structural unit (a1- 2)). The structural unit is more 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.
    [0032] [0032] R20! R ° * and R °° are preferably a methyl group.
    [0033] The structural unit (a1-0) includes, for example, a structural unit represented by any one of the formula (a1-0-1) to the formula (a1-0-12) and a structural unit wherein a methyl group corresponding to R °% * in the structural unit (a1-0) is substituted with 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).
    [0034] The structural unit (a1-1) includes, for example, the 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) of the formula (a1-1-4) and a structural unit in which a methyl group corresponding to R ° * in the structural unit (a1-1) is substituted with 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. ie PE; (a1-1-1) (a1-1-2) (a1-1-3) (a1-1-4)
    [0035] Examples of structural unit (a1-2) include a structural unit represented by any one of the formula (a1-2-1) to the formula (a1-2-6) and a structural unit in which a methyl group corresponding to R °° in the structural unit (a1-2) is substituted with a hydrogen atom, and a structural unit represented by any one of the formula (a1-2-2), the formula (a1-2-5) and the formula (a1-2-5) is preferred. you CHs you CHs 1e CHs The CHs I CHs you CHs = Ha = GI - = - Ö OQ 'OX PO (a1-2-1) (a1-2-2) (a1-2-3) (a1-2- 4) (a1-2-5) (a1-2-6)
    [0036] When the resin (A) includes a structural unit (a1-0), its content is usually 5 to 60 mol%, preferably 5 to 50 mol%, more preferably 10 to 40 mol%, on the basis of all the structural units of the resin (A).
    [0037] In structural unit (a1), examples of structural unit having a group (2) include a structural unit represented by formula (a1-4) (hereinafter sometimes referred to as "structural unit (a1-4) ) "): Ra32 CH, S (a1-4) Rass IL 34 (la Ve Râ O - + - 0-Ress Ra35 where, in the formula (a1-4), R222 represents a hydrogen atom, a d atom 'halogen or an alkyl group having 1 to 6 carbon atoms which may optionally have a halogen atom, R ° 53 represents a halogen atom, a hydroxy group, an alkyl group having 1 to 6 carbon atoms, a group alkoxy having 1 to
    [0038] Examples of the alkyl group in R °° and R23 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a pentyl group and a hexyl group. The alkyl group is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group, and more preferably a methyl group.
    [0039] In formula (a1-4), R °° is preferably a hydrogen atom, R233 is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably a methoxy group and an ethoxy group, and more preferably a methoxy group, 1a is preferably 0 or 1, and more preferably 0, R ° 3 * is preferably a hydrogen atom, and R ° 3 ° is preferably an alkyl group having 1 to 12 carbon atoms or an alicyclic hydrocarbon group, and more preferably a methyl group or an ethyl group.
    [0040] [0040] -OC (R2 *) (R235) -0-R3 ° 6 in structural unit (a1-4) is removed by contacting with an acid (eg p-toluenesulfonic acid) to form a hydroxy group.
    [0041] 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) with the formula (a1-4-12) and a structural unit in which a hydrogen atom corresponding to R ° in the structural unit (a1-4) is substituted with a methyl group, and more preferably the units structures represented by the formula (a1-4-1) to the formula (a1-4-5) and the formula (a1-4-10). Pat PET PET PET PET OLO. OO SD) 97 oC OO (a1-4-1) (a1-4-2) (a1-4-3) Lu 0 August p Le Et PET PET PET. By er © O. rs O os dos bo. L Eat T T 0 U (21.47) (a1-4-8) (a1-4-9) (a1-4-10) (a1-4-11) (a1-4-12)
    [0042] When the resin (A) includes the structural unit (a1-4), the content is preferably 10 to 95 mol%, more preferably 15 to 90 mol%, more preferably 20 to 85 mol%, of more preferably 20 to 70 mol%, and more preferably 20 to 60 mol%, based on the total of all structural units of the resin (A).
    [0043] 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) ").
    [0044] The halogen atom includes a fluorine atom and a chlorine atom and is preferably a fluorine atom. Examples of an alkyl group having 1 to 6 carbon atoms optionally having a halogen atom include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, a group. octyl, a fluoromethyl group and a trifluoromethyl group.
    [0045] The structural unit (a1-5) includes, for example, the structural units derived from the monomers mentioned in JP 2010-61117 A.
    [0046] 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 the structural units of the resin (A).
    [0047] [0047] Examples of the structural unit (a1) also include the following structural units.
    [0048] When the resin (A) includes the structural units mentioned above as (a1-3-1) to (a1-3-7), the content is preferably 10 to 95 mol%, more preferably 15 to 90 mole%, more preferably 20 to 85 mole%, more preferably 20 to 70 mole%, and more preferably 20 to 60 mole%, based on all the structural units of the resin (A).
    [0049] [0049] <Structural unit (s)> The structural unit (s) is derived from a monomer having no labile group in an acidic medium (hereinafter sometimes called "monomer (s)"). It is possible to use, as the monomer from which the structural unit (s) is derived, a monomer having no acid labile group known in the field of resists.
    [0050] [0050] <Structural unit (a2)> The hydroxy group possessed by the structural unit (a2) may be an alcoholic hydroxy group or a phenolic hydroxy group. When a resist pattern is produced from the resist composition of the present invention, in the case where high energy rays such as a KrF (248nm) excimer laser are used as the exposure source, an electron beam or extreme ultraviolet light (UVE), a structural unit (a2) having a phenolic hydroxy group is preferably used as a structural unit (a2), and a structural unit (a2-A) mentioned below is more preferably used. When using an ArF (193nm) excimer laser or the like, a structural unit (a2) having an alcoholic hydroxy group is preferably used as the structural unit (a2), and more preferably a structural unit (a2- 1) mentioned later. The structural unit (a2) can be included alone, or two or more structural units can be included.
    [0051] In structural unit (a2), examples of structural unit having a phenolic hydroxy group include a structural unit represented by formula (a2-A) (hereinafter sometimes referred to as "structural unit (a2-A) ”): Ho Ra50
    [0052] Examples of the halogen atom in R ° ® include a fluorine atom, a chlorine atom and a bromine atom.
    [0053] [0053] Examples of * -X °° 1- (A252-X252) pp ”include * -O-, * -CO-O-, * - O-CO-, * -CO-0-A252-CO- 0-, * -0-CO-A352-0-, * -OA ° -CO-O-, * -CO-0-A% - O-CO- and * -0-CO-A% ° 2 -0-CO-. Of these, * -CO-O-, * -CO-0-A332-CO-0- or * -0-A-52-CO-0- are preferred.
    [0054] 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.
    [0055] [0055] A is preferably a single bond, * -CO-O- or * -CO-O- A252-CO-O-, more preferably a single bond, * -CO-O- or * -CO-O- CH2-CO -O-, and more preferably a single bond or * -CO-O-.
    [0056] [0056] mb is preferably 0, 1 or 2, more preferably 0 or 1, and particularly preferably 0.
    [0057] Examples of structural unit (a2-A) include structural units derived from the monomers mentioned in JP 2010-204634 A and JP 2012-12577 A.
    [0058] 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.
    [0059] Examples of a 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)" ).
    [0060] In formula (a2-1), L ° * is preferably -O- or -O- (CH ”) j- CO-O- (fl represents an integer from 1 to 4), and more preferably -GOLD ! is preferably a methyl group, R3! 5 is preferably a hydrogen atom, RS is preferably a hydrogen atom or a hydroxy group, and ol is preferably an integer of 0 to 3, and more preferably 0 or 1.
    [0061] The structural unit (a2-1) includes, for example, the structural units derived from the monomers mentioned in JP 2010-204646
    [0062] 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%, and preferably further 1 to 20 mol%, and more preferably 1 to 10 mol%, based on all structural units of the resin (A).
    [0063] <Structural unit (a3)> The lactone ring carried by the structural unit (a3) can be a monocyclic ring such as a B-propiolactone ring, a y-butyrolactone ring or an α-valerolactone ring, or a condensed ring a 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.
    [0064] 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 can be included alone, or two or more structural units can be included:
    [0065] Examples of the aliphatic hydrocarbon group in R ° *, R322 R ° 23 and R22 include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, sec-butyl group and a tert-butyl group.
    [0066] In formula (a3-1) to formula (a3-3), preferably, L **, LP, and L® are each independently -O- or a group in which k3 is an integer from 1 to 4 in * -O- (CH2) ç3-CO-O-, more preferably -O- and * -O-CH> -CO-O-, and more preferably an oxygen atom, R218 R319 R220 and R22 ! are preferably methyl, 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 of 0 to 2, and more preferably 0 or 1.
    [0067] In 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, R22 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 1. In particular, the formula (a3-4) is preferably the formula (a3-4) ': Ra24 ted + C = O k (a3-4)'
    [0068] Examples of structural unit (a3) include structural units derived from the monomers mentioned in JP 2010-204646 A, from the monomers mentioned in JP 2000-122294 A and from the monomers mentioned in JP 2012-41274 A. The unit structural (a3) is preferably a structural unit represented by any one of the formula (a3-1-1), the formula (a3-1-2), the formula (a3-2-1), the 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 in which the methyl groups corresponding to R2! 3, RP, R220 and R ° 2 * in the formula (a3-1) in the formula (a3-4) are substituted with hydrogen atoms in the structural units below above.
    [0069] 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 of all the structural units of the resin (A). Each content of structural unit (a3-1), structural unit (a3-2), structural unit (a3-3) or structural unit (a3-4) is preferably 5 to 60 mol% , more preferably 5 to 50 mol%, and more preferably 10 to 50 mol%, based on all the structural units of the resin (A).
    [0070] <Structural unit (a4)> Examples of structural unit (a4) include the following structural units: H, RA + O (a4) 0 Nu where, in formula (a4),
    [0071] Examples of structural unit (a4) include a structural unit represented by at least one selected from the group consisting of formula (a4-0), formula (a4-1), formula (a4-2) , the formula (a4-3) and the formula (a4-4):
    [0072] Examples of the divalent aliphatic saturated hydrocarbon group in L ‘° include linear alkanediyl groups such as methylene group, ethylene group, propane-1,3-diyl 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 group 2-methylpropane-1,2-diyl.
    [0073] Examples of 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) in the following structural units is substituted with a hydrogen atom: Lee Je SS SS ce F2 tr, F3 za Ed nd on (24-0-2) (a4-0-3) oa) # 09 909) Pt A ee A @ + 07) @ + 08) (24-0-8) eo 0) (a4-0-11) (a4-0-12) bé ds Cas Ps Cas 275 = 2 of ENE ° (a4-0-13) (a4-0-14 ) (a 40 15) (a4-0-16)
    [0074] [0074] H, Ra41 Le ST
    [0075] [0075]
    [0076] Examples of the substituent carried by 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 the halogen atom - include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom is preferred: ok —— X243— a 845 (a-g3 )
    [0077] Examples of aliphatic hydrocarbon group in A2 *% include alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, a decyl group, a dodecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group and an octadecyl group; monocyclic alicyclic hydrocarbon groups such as cyclopentyl group, cyclohexyl group, cycloheptyl group and cyclooctyl group; and polycyclic alicyclic hydrocarbon groups such as a decahydronaphthyl group, an adamantyl group, a norbornyl group and the following groups (* represents a binding site): Examples of a group formed by combination include a group obtained by combining one or more alkyl groups or one or more alkanediyl groups with one or more alicyclic hydrocarbon groups, and include an alkanediyl group-alicyclic hydrocarbon group, an alicyclic hydrocarbon group-alkyl group, an alkanediyl group-alicyclic hydrocarbon group-alkyl group and the like.
    [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 R2 * is a saturated hydrocarbon group having the group represented by the formula (a-g3), R ** is more preferably a group represented by the formula (a-g2): + —A246 - xa44 _ — _ Aa47 (ag 2) where , in formula (a-g2), A3 * ° represents a divalent saturated hydrocarbon group having 1 to 17 carbon atoms optionally having a halogen atom, X represents ** - O-CO- or ** - CO-O- (** represents a binding site to A2 # 5), A7 represents a saturated aliphatic hydrocarbon group having 1 to 17 carbon atoms optionally having an atom of halogen, the total number of carbon atoms of A % 6 A 7 and X ° ** is 18 or less, and at least one of A %% and A37 has at least one halogen atom, and
    [0080] The number of carbon atoms of the saturated hydrocarbon group for A ° * ° is preferably 1 to 6, and more preferably 1 to 3.
    [0081] The preferred structure of the group represented by the formula (a-g2) is the following structure (* is a carbonyl group binding site).
    [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 group and hexane-1 group, 6-diyl; 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.
    [0083] Examples of divalent saturated hydrocarbon group represented by A *, A 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 an alicyclic saturated hydrocarbon group divalent. Specific examples thereof include a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group, a 1- group. methylpropane-1,3-diyl, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group and the like.
    [0084] In a 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 bond, and ** is a -O-CO-R® ** binding site,
    [0085] Examples of structural unit represented by formula (a4-1) include the following structural units, and structural units in which a methyl group corresponding to A ° * in the structural unit represented by formula (a4- 1) in the following structural units is substituted with a hydrogen atom.
    [0086] Hs Hs H Hs Hz er Hs 3 CH Te O O er: 0 Hz 0 ko
    [0087] Examples of structural unit represented by formula (a4-1) include a structural unit represented by formula (a4-2): Hz fs TT
    [0088] Examples of the alkanediyl group having 1 to 6 carbon atoms of L ** include the same groups as those mentioned for the alkanediyl group A *, Examples of the saturated hydrocarbon group of R include the same groups as those mentioned for R ° 2.
    [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 R in the structural unit (a4-2) is substituted with a hydrogen atom is also exemplified as the structural unit represented by the formula (a4-2).
    [0090] Examples of the structural unit (a4) include a structural unit represented by the formula (a4-3): Ho RP PD
    [0091] Examples of the alkanediyl group in L ° include those which are the same as mentioned in the alkanediyl group in the divalent saturated hydrocarbon group of A @ *, The divalent saturated hydrocarbon group optionally having a fluorine atom in A ** is preferably a divalent aliphatic saturated hydrocarbon group optionally having a fluorine atom and a divalent alicyclic saturated hydrocarbon group optionally having a fluorine atom, and more preferably a perfluoroalkanediyl group.
    [0092] In formula (a4-3), L ° is preferably an ethylene group.
    [0093] The structural unit represented by the formula (a4-3) 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 R ”in the structural unit (a4-3) is substituted with a hydrogen atom is also exemplified as the structural unit represented by the formula (a4-3).
    [0094] It is also possible to cite by way of example, as structural unit (a4), a structural unit represented by the formula (a4-4): + RC
    [0095] Examples of the saturated hydrocarbon group for R22 include those which are the same as the saturated hydrocarbon group represented by R2 * 2. R ° 2 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 carbon atoms having a fluorine atom.
    [0096] In the formula (a4-4), Af ! is preferably - (CH2); 1-, more preferably an ethylene group or a methylene group, and more preferably a methylene group.
    [0097] 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.
    [0098] 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 basis of all the structural units of the resin (A).
    [0099] <Structural unit (a5)> Examples of a non-leaving hydrocarbon group carried by 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.
    [0100] [0100] The alicyclic hydrocarbon group in R can be monocyclic or polycyclic. The monocyclic alicyclic hydrocarbon group includes, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group and a cyclohexyl group. The polycyclic alicyclic hydrocarbon group includes, for example, an adamantyl group and a norbornyl group.
    [0101] [0101] 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 an oxygen atom binding site.
    [0102] [0102] L is preferably a divalent aliphatic saturated hydrocarbon group having 1 to 8 carbon atoms, and more preferably a methylene group or an ethylene group.
    [0103] [0103] The group represented by the formula (L1-1) includes, for example, the following divalent groups.
    [0104] [0104] The group represented by the formula (L1-2) includes, for example, the following divalent groups.
    [0105] [0105] The group represented by the formula (L1-3) includes, for example, the following divalent groups. CH; 0 U AA ANA From AA Ö Hs
    [0106] [0106] The group represented by the formula (L1-4) includes, for example, the following divalent groups. O kk NGA ”AT A AG x x x Q xk DIS DA DA
    [0107] [0107] L ° ”is preferably a single bond or a group represented by formula (L1-1).
    [0108] [0108] Examples of structural unit (a5-1) include the following structural units and structural units in which a methyl group corresponding to R ° in the structural unit (a5-1) in the following structural units is substituted with a hydrogen atom. Hs H3 Hs Hs nu, Eh u €: [and 0 “rt 0 te o ett {ett O“ irons ooo (a5-1-1) (a5-1-2) (a5-1-3) (a5-1 -4) (a5-1-5) (25-16) Hs Hs Hs Hs Hz Hz in 5 enz in Tr enz ten o oO o is (a5-1-7) (a5-1-8) (a5-1 -9) (a5-1-10) (a5-1-11) (a5-1-12)
    [0109] [0109] <Structural unit (II)> The resin (A) can 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.
    [0110] [0110]
    [0111] [0111] Examples of the halogen atom represented by R include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
    [0112] [0112] 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.
    [0113] [0113] Examples of the organic cation of ZA * include an organic onium cation, an organic sulfonium cation, an organic iodonium cation, an organic ammonium cation, a benzothiazolium cation and an 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 formula (b2-1) to formula (b2-4) (hereinafter sometimes referred to as "cation (b2-1)" depending on the number. the formula).
    [0114] [0114] N res (R ””) m2 (RP) 269 9 R of Cr Vo! IS ’CHR R R Rb11 (b2-1) (b2-2) (b2-3) (RP13) 2 (RP) 2 LA A St (b2-4)
    [0115] The aliphatic hydrocarbon group represents a chain hydrocarbon group and an alicyclic hydrocarbon group.
    [0116] [0116] Examples of the alicyclic hydrocarbon group in which a hydrogen atom is substituted with an aliphatic hydrocarbon group include a methylcyclohexyl group, a dimethylcyclohexyl group, a 2-methyladamantan-2-yl group, a 2-ethyladamantan-2- group. 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.
    [0117] [0117] Examples of an aromatic hydrocarbon group include aryl groups such as phenyl group, biphenyl group, naphthyl group, anthryl group, phenanthryl group. The aromatic hydrocarbon group may have a chain hydrocarbon group or an alicyclic hydrocarbon group and examples of the aromatic hydrocarbon group having a chain hydrocarbon group include a tolyl group, a xylyl group, a cumenyl group, a mesityl group, a p- group. ethylphenyl, a p-tert-butylphenyl group, a 2,6-diethylphenyl group, a 2-methyl-6-ethylphenyl group, and the like and examples of the aromatic hydrocarbon group having an alicyclic hydrocarbon group include a p-cyclohexylphenyl group, a p-adamantylphenyl group and the like.
    [0118] [0118] Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a decyloxy group and a dodecyloxy group.
    [0119] The ring formed by bonding R ° * and RP with one another, with the sulfur atoms to which R® * and R ”are linked, can be a monocyclic, polycyclic, aromatic, non-aromatic ring, saturated or unsaturated. This ring includes a ring having 3 to 18 carbon atoms and is preferably a ring having 4 to 18 carbon atoms. The sulfur-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 binding site.
    [0120] [0120] 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 (tetrahydrothiophenium ring), a thian-1-ium ring, a 1,4-oxathian-4-ium ring and the like. The ring formed by combining RE “and RP! 2 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. Examples of these include an oxocycloheptane ring, an oxocyclohexane ring, an oxonorbornane ring, an oxoadamantane ring and the like.
    [0121] 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.
    [0122] [0122] -c- c- b2-c-23 -c- c- © © (b2-c-21) (b2-c-22) (b2-c-23) (b2-c-24) (b2 -c-25) (02028) (62027)
    [0123] [0123] Examples of cation (b2-2) include the following cations and the like. + + + DQ Dd OO (b2-c-28) (b2-c-29) (b2-c-30)
    [0124] [0124] Examples of cation (b2-3) include the following cations and the like.
    [0125] [0125] Examples of cation (b2-4) include the following cations and the like. 0-0 OOo Oren ® (b2-c-35) (D (b2-c-36) ® (b2-c-37) HzC, HsC HsC 0-0 OO Oren HsC D (b2-c-38) H Ke , (b2-c-39) D (b2-c-40) = 9 3) t-CaHo F0 BC sch 4 O0 (y (b2-c-41) (4; ° Hs HC (b2-0-42) (4 (b2-c-43) t-CaHo tC4Hs tC4Hs OOo 0-0 SO Orten ® (b2-c-44) (y (b2-c-45) (y (b2-c-46) t-C4He t -CaHo
    [0126] [0126] The structural unit represented by the formula (II-2-A ") is preferably a structural unit represented by the formula (II-2-A): RIIS
    [0127] [0127] The structural unit represented by the formula (II-2-A) is preferably a structural unit represented by the formula (II-2-A-1): RIIS
    [0128] [0128] The structural unit represented by the formula (II-2-A-1) is preferably a structural unit represented by the formula (II-2-A-2):
    [0129] [0129] The structural unit represented by the formula (II-2-A ") includes, for example, the following structural units, structural units in which a group corresponding to a methyl group of RS 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 optionally have a halogen atom (for example, a trifluoromethyl group, etc.) and the structural units mentioned in WO 2012/050015 A. ZA ”represents an organic cation.
    [0130] [0130] The structural unit having a sulfonio group and an organic anion in a side chain is preferably a structural unit represented by the formula (II-1-1): R114 on, ai (I1-1-1) o70— A! "1-RI + 8 <Rll2
    [0131] [0131] Examples of a structural unit including a cation in the formula (II-1-1) include the following structural units and structural units in which a group corresponding to R! * Is substituted by a hydrogen atom, a fluorine atom, a trifluoromethyl group or the like.
    [0132] [0132] Examples of the organic anion represented by A include a sulfonic acid anion, a sulfonylimide anion, a sulfonylmethide anion and a carboxylic acid anion. The organic anion represented by A is preferably a sulfonic acid anion, and the sulfonic acid anion is preferably an anion included in the subsequently mentioned salt represented by the formula (B1).
    [0133] [0133] Examples of the sulfonylimide anion represented by A include the following. F2 CF Fa £ C -CF3 E - 2 Op CF 0292 02 $ -CF2 os F2 op | Ì 7 N Ÿ F2 O2 —CF3 ose O2S-GF2 F, 0.4 dr, 04 F3 F, C-C —CF3
    [0134] [0134] Examples of the sulfonylmethide anion include the following.
    [0135] [0135] Examples of the carboxylic acid anion include the following. O 0 0 D _ Ho HC A HEA een Oe
    [0136] [0136] Examples of structural unit represented by formula (II-1-1) include structural units represented by the following formulas. Hs Hz Hs Hz Hz Hz ç + ç RAF ì RAF FE He T ° SX Pre) Hs Hs Hz will make irons D H tot D [9 TE F H os Fo OC. F Fr _ SE 3 a bone bone
    [0137] 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 the structural units of the resin (A).
    [0138] [0138] The resin (A) can include structural units other than the structural units mentioned above, and examples of such structural units include structural units well known in the art.
    [0139] 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 (a1) and a monomer (s).
    [0140] [0140] <Resin other than resin (A)> Regarding the resist composition of the present invention, the resin other than resin (A) can be used in combination.
    [0141] [0141] When the resist composition includes the resin (X), the content is preferably 1 to 60 parts by mass, more preferably 1 to 50 parts by mass, more preferably 1 to 40 parts by mass, more preferably 1 to 30 parts by mass, and more preferably 1 to 8 parts by mass, based on 100 parts by mass of the resin (A).
    [0142] [0142] 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 wt% or more and 99 wt% 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.
    [0143] [0143] <Acid Generator (B)> A nonionic or ionic acid generator can be used as an acid generator (B). Examples of the nonionic acid generator include sulfonate esters (eg, 2-nitrobenzyl ester, aromatic sulfonate, oxime sulfonate, N-sulfonyloxyimide, sulfonyloxyketone, diazonaphthoquinone 4-sulfonate), sulfones (eg, disulfone, ketosulfone, 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 anion of the onium salt include a sulfonic acid anion, a sulfonylimide anion, a sulfonylmethide anion and the like.
    [0144] [0144] The acid generator (B) is preferably an acid generator containing fluorine, and more preferably a salt represented by formula (B1) (hereinafter sometimes called “acid generator (B1). "): + -O, S 7 LM + - 3 dy (B1) 1 where, in formula (B1), QP! And QP 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, -CHz- included in the divalent saturated hydrocarbon group may be replaced by -O- or -CO-, and a hydrogen atom included in the hydrocarbon group saturated divalent 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 18 carbon atoms which may have a substituent, and -CH> - included in the alicyclic hydrocarbon group can be replaced by -O-, -S (0) z- or -CO-, and Z 'represents a cation o organic.
    [0145] [0145] Examples of the perfluoroalkyl group represented by Q ”and QP2 include a trifluoromethyl group, a perfluoroethyl group, a perfluoropropyl group, a perfluoroisopropyl group, a perfluorobutyl group, a perfluorosec-butyl group, a perfluorotert-butyl group, a perfluoropentyl group. and a perfluorohexyl group.
    [0146] [0146] 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.
    [0147] [0147] The group in which -CHz- included in the divalent saturated hydrocarbon group represented by L ”is replaced by -O- or -
    [0148] [0148] N O 03 ax LO 1:05 x Oo x No A; ba T _ DS, be ”077
    [0149] In the groups represented by the formula (b1-1) in 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.
    [0150] [0150] Examples of the group represented by the formula (b1-1) include the groups represented by the formula (b1-4) to the formula (b1-8).
    [0151] [0151] Examples of the group represented by the formula (b1-3) include the groups represented by the formula (b1-9) to the formula (b1-11).
    [0152] [0152] In the groups represented by the formula (b1-9) to the 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.
    [0153] [0153] Examples of an alkylcarbonyloxy group include an acetyloxy group, a propionyloxy group, a butyryloxy group, a cyclohexylcarbonyloxy group, an adamantylcarbonyloxy group and the like.
    [0154] [0154] Examples of the group represented by the formula (b1-4) include the following: O0 O O O CH3
    [0155] [0155] Examples of the group represented by the formula (b1-5) include the following: ASP Ao A Ao Aten Ao. Ae AL Ane Ô CH CHs CHs cu 2 O 3 Hs x AH AA A = OO Yo. As EN 79.0 O, O Ö Ö
    [0156] [0156] Examples of the group represented by the formula (b1-6) include the following: Anr Ar At 5 CO tbe "3 3 3 Atke" Arte Abo "Ad Ag
    [0157] [0157] Examples of the group represented by the formula (b1-7) include the following:
    [0158] [0158] Examples of the group represented by the formula (b1-8) include the following: De ae ES O
    [0159] [0159] Examples of the group represented by formula (b1-2) include the following: N 0 “A Ht AA wg A AKA, Hs Hz 3 Hs 4 Ha 2 Q Oo F 0 F As ds Ao. By As AA Hs
    [0160] [0160] Examples of the group represented by the formula (b1-9) include the following:
    [0161] [0161] Examples of the group represented by the formula (b1-10) include the following: Ha Ha Hz A AAS Al, DOW ‚oA„ a Da Lg x oA ae A DO “0 br + A DO word oA: pe 095 re ne FFF Fr F F3 Ade Jp Ane Arre Ae F “EF Ö FC OH Of H CH3 F F3 F F3, F F3 AP endow H O
    [0162] [0162] Examples of the group represented by the formula (b1-11) include the following:
    [0163] [0163] Examples of the alicyclic hydrocarbon group represented by Y include groups represented by formula (Y1) to formula (Y11) and formula (Y36) to formula (Y38).
    [0164] [0164] 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, a group glycidyloxy, a group - (CHz) ja-CO-OR®! or a group - (CH2); - O-CO-RE (where RP represents an alkyl group having 1 to 16 carbon atoms, an alicyclic hydrocarbon group having 3 to 16 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms, or groups obtained by combining these groups, ja represents an integer from 0 to 4, -CH> - included in an alkyl group and the alicyclic hydrocarbon group can be replaced by -O-, -S (O) z- or -CO-, a hydrogen atom included in the alkyl group, and the alicyclic hydrocarbon group and the aromatic hydrocarbon group may be substituted with a hydroxy group or a fluorine atom) and the like.
    [0165] [0165] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
    [0166] [0166] Examples of Y include the following CHs CH3 H3C1, CH3 OH 0 NV NN IN IN) NS oH-E UV A acdddge ewa 9 :. O CH; E ur e 10: oO CH3 oO CHz o CH3 0 q 0> 70 70 DAL O Oo © 0, 0. Q, 3 | X> a A X + Lo SEE 06 SP arS PP cho dd O
    [0167] [0167] Y is preferably an alicyclic hydrocarbon group 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-. Y is more preferably an adamantyl group, a hydroxyadamantyl group, an oxoadamantyl group, or groups represented by the following formulas.
    [0168] [0168] The anion in the salt represented by formula (B1) is preferably an anion represented by formula (B1-A-1) to formula (B1-A-55) [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-55).
    [0169] [0169] OH Oo OH el a2 b1 62 _ Q Co. vi _ oh! ab oss O3S L os D AM 3 A
    [0170] [0170]
    [0171] [0171] Qp1 052 oO CHs ax Ca 9 CHs - On A4 os> LA 038 L ° o 0 0 0, O (B1-A-25) (B1-A-26) | | OH ar O2 oO CH Qb1 QM - Sp Os ° F ja 0 ° 70 F pa O TO 035 o "038 oker os Voer O 5 Qb2 FQF> OL Oo L B1-A-27) (B1-A-28) Cls ( B1-A-29) CHs 0, OS sp RS b1 62 O is Ri7 ob! La "co" Q aa R 0 0 O + SL 0 (B1-A-30) (BL-A-31) (B1-A -32)
    [0172] [0172] ee gi a a ” Re 8 ”A4 PT A4 0 - | = L = SP LA4 és TY So ss PF O Ô Qb2 È Qb2 È (B1-A-33) (B1-A-34) (B1-A-35) F F F H
    [0173] [0173] oO OOA MN and eo 0 © 0- 9> 0 D b1 b2 [} 9 QQO b1 b2 b1 b2 Q 'AOQ ”AO 7 TS OÙ - Sr 0. LK 7 os 0: (B1-A-47) 9 (B1-A-48) 9 (B1-A-49)
    [0174] Preferred anions in the salt represented by formula (B1) are anions represented by formula (B1a-1) through formula (B1a-34).
    [0175] [0175] F
    [0176] [0176] Among these, anion represented by any one of the formula (B1a-1) to the formula (B1a-3) and of the formula (B1a-7) to the formula (B1a-16), the formula (B1a-18), formula (B1a-19) and formula (B1a-22) to formula (B1a-34) is preferable.
    [0177] [0177] Examples of the organic cation of Z * include an organic cation onium, an organic sulfonium cation, an organic iodonium cation, an organic ammonium cation, a benzothiazolium cation and an organic phosphonium cation, and include those identical to the organic cation ZA ” in the structural unit represented by the formula (II-2-A "). Among them, an organic sulfonium cation and an organic iodonium cation are preferable, and an arylsulfonium cation is more preferable.
    [0178] [0178] The acid generator (B) is a combination of the aforementioned anions and the aforementioned organic cations, and these can optionally be combined. Examples of the acid generator (B) are preferably combinations of an anion represented by any one of formula (B1a-1) to formula (B1a-3) and formula (B1a-7) to formula (B1a-16), formula (Bla 18), formula (B1a-19) and from formula (B1a-22) to formula (B1a-34) with a cation (b2-1) or a cation (b2-3).
    [0179] Examples of the acid generator (B) are preferably those represented by formula (B1-1) to formula (B1-48). Of these, 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 ( B1-48) are particularly preferable.
    [0180] [0180] I KF © KF X CD AT + TD Oo ”+ Ô 03 (B1-13) © (B1-14) (B1-15) ü [) © + @ KF H ON F 0 = + ooi JX” ” 048 a (B1-16) O von Voo
    [0181] [0181]
    [0182] [0182] |
    [0183] [0183]
    [0184] [0184] In the resist composition of the present invention, the content of acid generator is preferably 1 part by mass or more and 45 parts by mass or less, preferably 1 part by mass or more and 40 parts by mass or less, more preferably 3 parts by mass or more and 35 parts by mass or less based on 100 parts by mass of the resin (A). The resist composition of the present invention can include either the acid generator (B) alone or a plurality of acid generators.
    [0185] [0185] <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 known analytical means such as liquid chromatography or gas chromatography.
    [0186] [0186] <Other components> The resist composition 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 dyes.
    [0187] [0187] <Preparation of resist composition> The resist composition of the present invention can be prepared by mixing a salt (I), a resin (A), an acid generator (B), and if necessary, resins other than resin (A), a solvent (E), a deactivating agent (C) and other components (F). The order of mixing these components is any order and is not particularly limited. It is possible to choose, as the temperature during mixing, a suitable temperature of 10 to 40 ° C, depending on the type of the resin, the solvent solubility (E) of the resin and the like. It is possible to choose, as the 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 stirring. After mixing the respective components, the mixture is preferably filtered through a filter having a pore diameter of about 0.003 to 0.2 µm.
    [0188] [0188]
    [0189] [0189] (Applications) The resist composition of the present invention is suitable as a resist composition for exposure to a KrF excimer laser, a resist composition for exposure to an ArF excimer laser, a resist composition for exposure to a KrF excimer laser. electron beam (FE) or a resist composition for exposure to extreme ultraviolet (UVE), and more suitable as a resist composition for electron beam exposure (FE) (or EB for electon beam) or as a composition of resist for exposure to UVE and the resist composition is useful for the fine processing of semiconductors.
    [0190] [0190] 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.
    [0191] [0191] Example 1: synthesis of the salt represented by the formula (I-1) CF OR OR, vn TT ta) (k1b] ONS 1-0} NA gum + 70 Lelei A En das (1) 5.00 parts d 'a compound represented by formula (I-1-a), 10 parts of chloroform, 4.52 parts of a compound represented by formula (I-1-b) and and 4.45 parts of trifluoromethanesulfonic acid have was mixed, which was followed by stirring at 23 ° C for 30 minutes and further cooling to 5 ° C. 7.79 parts of trifluoroacetic anhydride were added dropwise to the resulting mixture over 15 minutes, which was followed by stirring at 23 ° C for 1 hour.
    [0192] [0192] Example 2: Synthesis of the salt represented by the formula (I-14) 8 8 9 CF3SO3H OD ODO Dam TT A Rares Oo OOH | oe oor. ne (I-1-a) (1-14-b) OMe (44.0)
    [0193] [0193] Example 3: synthesis of the salt represented by formula (I-17) 8 MeO COOMe CF: SO: HQ: DO CF3SO7 ND + De o Oo MeO COOMe OMe cr hoar, HO (1e) (I-17-b ) Me NaOH ion exchange resin NaOH oxalic acid AD _ TS MeO oo CF3S0; => cr DO
    [0194] [0194] Example 4: synthesis of the salt represented by formula (I-16) F. FFF MeO COOMe CF3SO3H AO CF3SO3 eue + Ie Oo Oo MeO COOMe 0 OMe cp MeO (I-16-a) (I-16-b ) Me
    [195] [195] Example 5: Synthesis of the salt represented by the formula (I-19)
    [0196] [0196] Synthesis of Resin The compounds (monomers) used in the synthesis of the resin (A) are indicated below. Hereinafter, these compounds are referred to as “monomer (a1-1-3)” depending on the number of the formula. CHs CH HK HK 5 O O
    [0197] [0197] Synthesis Example 1 [Synthesis of Resin A1] A monomer (a1-4-2), a monomer (a1-1-3) and a monomer (a1-2-6) were used as monomers. , and these monomers were mixed in a molar ratio of 38:24:38 [monomer (a1-4-2): monomer (a1-1-3): monomer (a1-2-6)], and methyl isobutyl ketone was added to this mixture of monomers in an amount equal to 1.5 times the total mass of all monomers. To the mixture thus obtained, azobisisobutyronitrile as an initiator was added in an amount of 7 mol% based on the total molar number of all the monomers, which was followed by polymerization with heating at 85 ° C. for about 5 hours. To the polymerization reaction mixture thus obtained an aqueous solution of p-toluenesulfonic acid was added. After stirring for 6 hours, an organic layer was isolated by separation. The organic layer thus recovered was poured into a large amount of n-heptane to precipitate a resin, which was followed by filtration and collection to obtain an A1 resin (copolymer) having a weight average molecular weight of about 5.3 x 103 with a yield of 78%. This A1 resin includes the following structural units. CH3 Hs Lc, tot os
    [0198] [0198] <Preparation of Resist Compositions> As shown in Table 1, the following respective components were mixed and the mixtures thus obtained were filtered through a fluororesin filter having a pore diameter of 0.2 µm for preparing resist compositions.
    [0220] [0220] ableau 1 naked Salt generator (I) Copes agent N Acid resin deactivating (C Composition | A1 = B1-43 = I-1 = 110 ° C / 1 10 parts | 3.4 parts 0 , 7 part 120 ° C 2 10 parts | 3.4 parts 0.5 part 0.2 part 120 ° C Composition | A1 = B1-43 = [-14 = | 110 ° C / 3 10 parts | 3.4 parts 0.7 part 120 ° C Composition | A1 = B1-43 = I-16 = 110 ° C / 4 10 parts | 3.4 parts 0.7 part 120 ° C 5 10 parts | 3.4 parts 0.7 part 120 ° C 6 10 parts | 3.4 parts 0.7 part 120 ° C Composition | A1 = B1-43 = IX-1 = 110 ° C / Comparative | 10 parts | 3.4 parts 0.7 part 120 ° C 1
    [0199] [0199] <Resin> A1: resin A1 <Acid generator (B)>
    [0200] [0200] (Evaluation of the exposure of the resist composition with an electron beam) Each 6 inch (15.24 cm) diameter silicon wafer was treated with hexamethyldisilazane and then baked on a hot plate. direct at 90 ° C for 60 seconds. A resist composition was applied by centrifugal application (“spin coating”) to the silicon wafer so that the thickness of the composition layer was 0.04 μm. The coated silicon wafer was precooked on the direct hot plate at the temperature shown in the "PB" column of Table 1 for 60 seconds to form a composition layer. By means of a direct electron beam writing system [“ELS-F125 125 keV”, manufactured by ELIONIX INC.], Line and space patterns (pitch: 36 to 72 nm / line width : 18 to 36 nm) were entered directly while the exposure dose was changed in stages.
    [0201] [0201] <Evaluation of the resolution> In effective sensitivity, the resist pattern was observed by a scanning electron microscope and the minimum resolved line width was considered as the resolution. The results are shown in Table 2. The resolution (nm) is shown. Example 6 Composition 1 Example 7 Composition 2 Example 8 Composition 3 Example 9 Composition 4 Example 10 Composition 5 Example 11 Composition 6 Composition Comparative Example 1 P. 26 nm Comparative 1 Compared with Comparative Composition 1, Compositions 1 to 6 exhibit satisfactory resolution.
    [0206] [0206] A salt and resist composition comprising the salt of the present invention show satisfactory resolution and are therefore useful for fine processing of semiconductors. It is also possible to obtain the salt of the present invention in a high yield.
    权利要求:
    Claims (16)
    [1]
    1. A salt represented by formula (I): R ° (Rò) m3 R2 | ° Ss 70> Q., y (RS) ms (RE) ma where, in formula (I), R * and R2 each independently represent a hydrocarbon group having 1 to 18 carbon atoms, and -CH> - included in the hydrocarbon group may be replaced by -O- or -CO-, R3, R * and R ° each independently represent a halogen atom, an alkyl fluoride group having 1 to 6 carbon atoms or a hydrocarbon group having 1 with 18 carbon atoms, and -CH> - included in the hydrocarbon group can be replaced by -O- or -CO-, m3 represents an integer from 0 to 2, and when m3 is 2, two R3 can be the same or different from each other, m4 represents an integer from 0 to 5, and when m4 is 2 or more, a plurality of R * may be the same or different from each other, and m5 represents an integer from 0 to 5, and when m5 is 2 or more, a plurality of R ° may be the same or different from each other.
    [2]
    2. The salt according to claim 1, wherein R * represents an alkyl group having 1 to 6 carbon atoms, and -CHz- included in the alkyl group may be replaced by -O- or -CO-.
    [3]
    3. The salt according to claim 1, wherein R * represents an alkyl group having 1 to 6 carbon atoms, and -CH: - included in the alkyl group can be replaced by -O- or -CO-.
    [4]
    4. The salt according to claim 1, wherein R * represents a fluorine atom, an alkyl fluoride group having 1 to 4 carbon atoms, an alkyl group having 1 to 6 carbon atoms or an alicyclic hydrocarbon group having 3. with 10 carbon atoms and -CH: - included in the alkyl group and the alicyclic hydrocarbon group can be replaced by -O- or —CO-
    [5]
    5. The salt according to claim 1, wherein R * and R ° each independently represent a fluorine atom, an alkyl fluoride group having 1 to 4 carbon atoms, an alkyl group having 1 to 6 carbon atoms or an alkyl group having 1 to 6 carbon atoms or a alicyclic hydrocarbon group having 3 to 10 carbon atoms and -CH: - included in the alkyl group and the alicyclic hydrocarbon group can be replaced by -O- or -CO-.
    [6]
    6. The salt of claim 1, wherein m3 represents 0 or 3.
    [7]
    7. The salt of claim 1, wherein m4 and m5 each independently represent an integer of 0 to 2.
    [8]
    8. The salt of claim 1, the salt being represented by any one of formula (I-1) to formula (1-20):
    | in ae Ses “a L> + Ÿ go N $ em ca XN wi> ee ï A SE SSSR iS 3 - 'y EN ET ea Ti ei 3 SS Og PE j ff $ x 3 ad EE dx 5 3 x Là ï Di et aj Ÿ gl ptet ie Sj> a Be,. 6 Zet jj is ii Be "So ce se À À $ a 0 Et Lu Fee FE © TO vu. NN de. A Fe AS = PT 0 Fr 5 ES, és ES © ES Ë a N © EN NA € ak ÉTAIT LAL es en aus a 8 EL ES [| $ Ÿ ÿ è 3 $ F Te Sas et Sas GEE VAS jrs ER> ve CAS 5 3} Ÿ en À ee 5 ta ses EA Ls Ÿ Le I LA pe ee Pf ee PT de me ie tie Ee a Se te L ï “x A IE LU en gs Xe ste El ml Le TE Ka Fe Se
    IN sat Ft she ans me se “2“ 3 ta X 13 & A 3 es À rt to EN Fe a # ex EE = “+ j = j = 3 st A to X if A: orn RÉ Mage = co Is EO i $ «IX Ne a NE Poe, ei SP Ni De + PE Fe, Ne = 4 ss an EN Se> Ÿ a | Tl Nn Ë „E ne ii en nl ge, im Le Mg Ba ° ri pe Es PAU EEE US} VPR LS:%> Bd“ a HE SET> ”a À% N _ Ss = 0.: ke 1 S ( 3 'SA are S 2 22, BE ed EU ST FF FE Ae Vr A nt ne 3 A $ Te FPE… ÈS… A6; en Ê 0 Se Sg KA ge # pes RE qe SEP ce LE, 38} Es En NE
    [9]
    9. A deactivating agent comprising a salt according to one of claims 1 to 8.
    [10]
    10. A resist composition comprising the deactivating agent of claim 9, a resin including a structural unit having an acid labile group, and an acid generator.
    [11]
    11. A resist composition according to claim 10, wherein the resin comprising a structural unit comprising an acid labile group includes at least one resin selected from the group consisting of a structural unit represented by formula (a1-1) and a. structural unit represented by the formula (a1-2): Ge # A ‚R | N + €} | = O | = O | LE =, Le 7}; YU re To Ra The CH hs fm) N To der (at-t) (a1-2) where in formula (a1-1) and formula (a1-2), L # and L ° each independently represent -O- or * -O- (CH>) 1-CO-O-, k1 represents an integer from 1 to 7, and * represents a binding site to -CO-, R ° * and R °° each independently represent a hydrogen atom or a methyl group, R °° and R each independently represent an alkyl group having 1 to 8 carbon atoms, an alicyclic hydrocarbon group having 3 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 from 0 to 3.
    [12]
    12. The resist composition of claim 10, wherein the resin comprising a structural unit having an acid labile group comprises a structural unit represented by the formula (a2-A):
    Hd. Rat | nn, a {22-A} (Je (R® ")} mb where in the formula (a2-A), R250 represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 atoms of carbon optionally having 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 alkylcarbonyl group having 2 to 4 carbon atoms, an alkylcarbonyloxy group having 2 to 4 carbon atoms, an acryloyloxy group or a methacryloyloxy group, A2 ° 0 represents a single bond or * -X °° 1- (a252-x252) 5; and * represents a binding site to the carbon atom to which -R2 ° is attached, A represents an alkanediyl group having 1 to 6 carbon atoms, x °° 1 and X each independently represent -O-, -CO- O- or -O-CO-, nb represents 0 or 1, and mb represents an integer of 0 to 4, and when mb is an integer of 2 or more, a plurality of R ° ** may be the same or different from each other others.
    [13]
    13. The resist composition of claim 10, wherein the acid generator includes a salt represented by formula (B1):
    Qt 2 OS LAS, {B1) [where in formula (B1), Q "* and Q ° Each independently represent a fluorine atom or a perfluoroalkyl group having 1 to 6 carbon atoms, LP Represents a hydrocarbon group divalent saturated having 1 to 24 carbon atoms, -CH> - included in the saturated hydrocarbon group may be replaced by -O- or -CO-, and a hydrogen atom included in the saturated hydrocarbon group may be substituted with one atom of fluorine or a hydroxy group, Y represents a methyl group which may have a substituent or an alicyclic hydrocarbon group having 3 to 18 carbon atoms which may have a substituent, and -CH> - included in the alicyclic hydrocarbon group may be replaced by -O-, -S (O)> - or -CO-, and Z * represents an organic cation.
    [14]
    14. The resist composition of claim 10 further comprising an acid generating salt having an acidity lower than that of an acid generated by the acid generator.
    [15]
    15. A method for producing a resist pattern, which comprises: (1) a step of applying the resist composition of claim 10 to a substrate, (2) a step of drying the applied composition to form a layer. composition, (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.
    [16]
    16. A process for producing a salt, which comprises:
    reacting a compound represented by formula (I-B) with a compound represented by formula (I-C) to produce a salt represented by formula (I): RT (R) ms 0 Ri (RO) R2 LQ $ R2 “4 | > 0 Ta.
    Hf (S (RS) ms zZ s 9 (D) ma Ops CT DD (I-B) (I-C) AR5) ms (D) ma (T)
    wherein in formula (I), formula (I-B) and formula (I-C),
    R * and R2 each independently represent a hydrocarbon group having 1 to 18 carbon atoms, and -CH> - included in the hydrocarbon group may be replaced by -O- or -CO-,
    R3, R * and R ° each independently represent a halogen atom, an alkyl fluoride group having 1 to 6 carbon atoms or a hydrocarbon group having 1 to 18 carbon atoms, and -CHz- included in the hydrocarbon group can be replaced by -O- or -CO-,
    m3 represents an integer from 0 to 2, and when m3 is 2, two R3s may be the same or different from each other,
    m4 represents an integer of 0 to 5, and when m4 is 2 or more, a plurality of R * may be the same or different from each other,
    m5 represents an integer of 0 to 5, and when m5 is 2 or more,
    a plurality of R ° may be the same or different from each other, and
    RE represents a hydrogen atom or a methyl group.
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    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    US20170329227A1|2016-05-11|2017-11-16|Shin-Etsu Chemical Co., Ltd.|Novel sulfonium compound, making method, resist composition, and pattern forming process|
    WO2019123895A1|2017-12-22|2019-06-27|富士フイルム株式会社|Active-light-sensitive or radiation-sensitive resin composition, resist film, pattern formation method, method for manufacturing electronic device, and compound|
    DE2150691C2|1971-10-12|1982-09-09|Basf Ag, 6700 Ludwigshafen|Photosensitive mixture and use of a photosensitive mixture for the production of a planographic printing plate|
    US3779778A|1972-02-09|1973-12-18|Minnesota Mining & Mfg|Photosolubilizable compositions and elements|
    DE2922746A1|1979-06-05|1980-12-11|Basf Ag|POSITIVELY WORKING LAYER TRANSFER MATERIAL|
    US5073476A|1983-05-18|1991-12-17|Ciba-Geigy Corporation|Curable composition and the use thereof|
    JPS6269263A|1985-09-24|1987-03-30|Toshiba Corp|Photosensitive composition|
    JPS62153853A|1985-12-27|1987-07-08|Toshiba Corp|Photosensitive composition|
    JPS6326653A|1986-07-21|1988-02-04|Tosoh Corp|Photoresist material|
    JPS63146038A|1986-12-10|1988-06-18|Toshiba Corp|Photosensitive composition|
    JPS63146029A|1986-12-10|1988-06-18|Toshiba Corp|Photosensitive composition|
    GB8630129D0|1986-12-17|1987-01-28|Ciba Geigy Ag|Formation of image|
    DE3914407A1|1989-04-29|1990-10-31|Basf Ag|RADIATION-SENSITIVE POLYMERS AND POSITIVE WORKING RECORDING MATERIAL|
    JP3763693B2|1998-08-10|2006-04-05|株式会社東芝|Photosensitive composition and pattern forming method|
    JP5487784B2|2008-08-07|2014-05-07|住友化学株式会社|Chemically amplified positive resist composition|
    TW201033735A|2008-12-11|2010-09-16|Sumitomo Chemical Co|Resist composition|
    JP5523854B2|2009-02-06|2014-06-18|住友化学株式会社|Chemically amplified photoresist composition and pattern forming method|
    JP5750242B2|2009-07-14|2015-07-15|住友化学株式会社|resist composition|
    US8460851B2|2010-01-14|2013-06-11|Sumitomo Chemical Company, Limited|Salt and photoresist composition containing the same|
    JP5807334B2|2010-02-16|2015-11-10|住友化学株式会社|Method for producing salt and acid generator|
    JP5691585B2|2010-02-16|2015-04-01|住友化学株式会社|Resist composition|
    JP5505371B2|2010-06-01|2014-05-28|信越化学工業株式会社|Polymer compound, chemically amplified positive resist material, and pattern forming method|
    JP5608009B2|2010-08-12|2014-10-15|大阪有機化学工業株式会社|Homoadamantane derivative, method for producing the same, and photoresist composition|
    US9182664B2|2010-10-13|2015-11-10|Central Glass Company, Limited|Polymerizable fluorine-containing sulfonate, fluorine-containing sulfonate resin, resist composition and pattern-forming method using same|
    TWI525066B|2011-04-13|2016-03-11|住友化學股份有限公司|Salt, photoresist composition, and method for producing photoresist pattern|
    JP6592896B2|2014-01-10|2019-10-23|住友化学株式会社|Resin and resist composition|
    JP6450660B2|2014-08-25|2019-01-09|住友化学株式会社|Salt, acid generator, resist composition, and method for producing resist pattern|
    JP6423681B2|2014-10-14|2018-11-14|住友化学株式会社|Resin, resist composition and method for producing resist pattern|
    法律状态:
    2021-06-28| FG| Patent granted|Effective date: 20210518 |
    优先权:
    申请号 | 申请日 | 专利标题
    JP2019104596|2019-06-04|
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