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WO2001068575A1 - Cation de type sel de fluoroalkylonium ou generateur d'acides generant des cations ou des acides lorsqu'il est irradie par des rayons d'energie - Google Patents

Cation de type sel de fluoroalkylonium ou generateur d'acides generant des cations ou des acides lorsqu'il est irradie par des rayons d'energie Download PDF

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WO2001068575A1
WO2001068575A1 PCT/JP2001/001060 JP0101060W WO0168575A1 WO 2001068575 A1 WO2001068575 A1 WO 2001068575A1 JP 0101060 W JP0101060 W JP 0101060W WO 0168575 A1 WO0168575 A1 WO 0168575A1
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Kenji Adachi
Sumi Ishihara
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Daikin Industries Ltd
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    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
    • C07D295/067—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents attached to the same carbon chain, which is not interrupted by carbocyclic rings
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    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
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    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D211/74—Oxygen atoms
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    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
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    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/46—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings substituted on the ring sulfur atom
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/08—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D345/00—Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5407—Acyclic saturated phosphonium compounds
    • C—CHEMISTRY; METALLURGY
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    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5449—Polyphosphonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/59—Hydrogenated pyridine rings
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • the present invention relates to fluorinated cations or acid generators which generate cations or acids upon irradiation with energy rays. . Background art
  • phosporium salts such as slumps and rhododiums have been exposed to actinic rays (e.g., ultraviolet rays, electron beams, X-rays, lasers, etc.) in the present specification. It is widely known that it absorbs and decomposes to generate a strong acid.
  • actinic rays e.g., ultraviolet rays, electron beams, X-rays, lasers, etc.
  • actinic rays e.g., ultraviolet rays, electron beams, X-rays, lasers, etc.
  • actinic rays e.g., ultraviolet rays, electron beams, X-rays, lasers, etc.
  • actinic rays e.g., ultraviolet rays, electron beams, X-rays, lasers, etc.
  • the present inventors have developed a high sensitivity that can improve the above performance.
  • Investigation of the acid generator of the present invention led to the discovery of a fluoroalkyl oxonium salt into which a fluoroalkyl group was introduced. Therefore, the purpose of the present invention is to produce cations or acid generators that are denatured by energy rays in fields such as photo resist.
  • An object of the present invention is to provide a compound which is effective as an agent and a chemically amplified resist material obtained by combining the compound. Disclosure of the invention
  • the above-mentioned problem of the present invention is to generate a cation or an acid by irradiation with energy, the formula (1):
  • A is an element selected from iodine, sulfur, selenium, tellurium, nitrogen or phosphorus;
  • R 2 and R 3 are absent, and R 1 is an alkyl group having 15 carbon atoms or a aryl group having 6 to 15 carbon atoms. ;
  • R 3 When A is sulfur, selenium or tellurium, R 3 is absent, and R and R 2 are each independently an alkyl group having 1 to 15 carbon atoms.
  • C7-C35 alkylalylamino group Is a diarylamino group having 12 to 40 carbon atoms, and shaku 1 and R 2 may be mutually bonded to form a ring;
  • R 1 , R 2 and R 3 are each independently an alkyl group having 1 to 15 carbon atoms, 6 to 20 aryl groups, 2 to 30 dialkylamino groups, carbon number? 1-3 5
  • a Le kills ⁇ rie was Le A Mi amino group or of Ri Oh di ⁇ Re Ichiru ⁇ Mi amino group having 1 2-4 0 carbon atoms, R 1 and R 2 and R 3 each each other May form one or more rings, or R 3 may be absent, and R 1 and R 2 may combine to form an aromatic ring containing A.
  • I is an alkyl group having 1 to 15 carbon atoms, 6 to 20 aryl groups, 2 to 30 dialkylamino groups, carbon number? 1-3 5
  • a Le kills ⁇ rie was Le A Mi amino group or of Ri Oh di ⁇ Re Ichiru ⁇ Mi amino group having 1 2-4 0 carbon atoms, R 1 and R 2 and R 3 each each other May form one or more rings, or R 3 may be absent, and R 1 and R 2 may combine
  • the aryl group, the alkyl group of the alkyl aryl group and the aryl group of the aryl amino group may be Alkyl group, octaalkyl group, halogen atom, alkoxy group, aryloxy group, nitro group, amide group, cyano group, alkanol group, It may be substituted with an arylyl group, an alkoxycarbonyl group, an aryloxycarbonyl group or an acyloxy group; R f is branched. Or a perfluoroalkyl group having 1 to 15 carbon atoms which may form a ring. A part of the fluorine of the fluoroalkyl group has been replaced with hydrogen;
  • X — is the conjugate base of Brentsted acid) or
  • R 5 X 1 R 8 (In the formula, A 1 and A 2 are the same or different, and each is an element selected from iodine, sulfur, selenium, tellurium, nitrogen, or phosphorus. Yes;
  • R 5 and R 8 are absent, and R 4 and R 7 are each independently a carbon atom of 1 to Alkyl group with 15 alkyl groups, aryl group with 6 to 20 carbon atoms, dialkylamino group with 2 to 30 carbon atoms, and alkyl library with 7 to 35 carbon atoms A ruamino group or a diarylamino group having 12 to 40 carbon atoms;
  • R 4 , R 5 , R 7 and R 8 are each independently an alkyl having 1 to 15 carbon atoms.
  • the above-mentioned alkyl group, the alkyl group of the dialkylamino group and the alkyl group of the alkylaryl amino group are an aryl group, a halogen group. It may be substituted by a carbon atom, an oxygen atom, a nitrogen atom, a sulfur atom, or a silicon atom, may be branched, may form a ring,
  • the aryl group, the alkyl group and the aryl group of the aryl and amino groups are the alkyl group, the alkyl group and the alkyl group.
  • R 6 is an aryl group, a halogen atom, an oxygen atom, a nitrogen atom, a sulfur atom or a silicon atom.
  • R f may be a branched or may form a ring, a perfluoroalkyl group having 1 to 15 carbon atoms, or a perylfluoroalkyl group A part of the fluorine of the above has been replaced by hydrogen;
  • X — is a conjugate base of brentsted acid), and relates to a cation or an acid generator in the form of a fluoroalkylonium salt represented by the formula:
  • R f in the above formula (1) or (2) _CH 2 R f 1 (R f 1 may be branched or may form a ring.
  • R f 2 CF 2 H R f 2 is a perfluoroalkylene group having 1 to 14 carbon atoms, which may be branched or form a ring.
  • Fluoroalkylene groups in which some of the fluorine in the fluoroalkylene group has been replaced with hydrogen or _CH 2 R f 3 CF 2 H (R f 3 is branched and A perfluoroalkylene group having 1 to 13 carbon atoms, which may form a ring, or a part of the fluorine of the perfluoroalkylene group is preferred. It has been replaced with hydrogen ), And X_ is preferably a conjugated base of fluoroalkylsulfonate.
  • Fluoroalkylene salt of the present invention Salt-type cation or acid generator is converted to a negative-type resist resin or a positive-type resist. By blending it with resin, highly sensitive chemically amplified resist materials can be manufactured. Best mode for carrying out the invention In general, the cation or acid generator binds to the core element A and to it by the irradiated energy. One of the moieties (substituents) is cut off, and the cut-off substituent becomes a cation or the anion removes a hydrogen atom to become an acid group. This generates cations or acids (J. Po1 ym. Sci. Part A: Po1 ym. Chem. 30, 23 65-23) 6 9 (1992); Macromo 1 ecu 1 es, 24, 2 13 7-2 13 9 (1 9 9)).
  • the core element A has higher cationicity and higher reactivity than the acid generators. However, it can be a cation generator or an acid generator with much higher sensitivity to energy rays.
  • the substituent constant (am) of the Hammett of each substituent was-0.06 for the methyl group, 0.04 for the phenyl group, and 10 for the benzyl group.
  • the trifluoromethyl group is 0.46 (edited by The Chemical Society of Japan,
  • fluoroalkylonium salts are used in the field of synthetic organic chemistry to introduce fluoroalkyl groups into various organic compounds. It has only been disclosed as a test reagent.
  • A is For sulfur, selenium or tellurium, where R 1 is an alkyl group or an aryl group and R 2 is an aryl group, Zh.Org. , 15, 2432 (1979), and J. Org. Chem. USSR, 15, 222 (1977).
  • R f and have contact to or formula (1) is - if CH a R f 1 Ah Ru in, A is also R f 1 group in sulfur Ru Ah with CF 3, in R 1, R 2 co It has been reported that the synthesis of a methyl group, a phenyl group together, and a phenyl group bonded to form a ring are also possible. (Bull. Chem. Soc. Jpn. 64, 2008 (1991)). In the formula (1), when A is sulfur and R 1 and R 2 are both a dialkylamino group, Chem. Ber., 124, 31 ( 1 9 9 1).
  • fluoroalkionium salts that can be used in the present invention, but are not limited to these but are examples.
  • fluoroalkyronedium salts described in the above-mentioned documents can also be used.
  • X in the fluoroalkionium salt used in the present invention is a synergistic base for blended acid.
  • prested acid include trifluorene sulfonic acid, tetrafluorene sulfonic acid, and perfluorinated acid.
  • fluoroalkylsulfuric acid such as sulfonic acid, difluoromethansulfonate, etc., methansulfonic acid, and Chromosome sunsulphonic acid, benzenesulphonic acid, toluenesulphonic acid, sulfuric acid, fluorosulphonic acid, chlorosurul Ho phosphate, HBF 4, HS b F 6 , HPF 6, HS b C l 5 F, HS b C l 6, HA s F 6, HBC 1 3 F, HA 1 C 1 4 , etc.
  • Re is Ah up al But is limited to this is not .
  • fluoroalkyl sulfonate is preferred because it is a strong acid and does not generate hydrogen fluoride or hydrogen chloride.
  • the cation or acid generator of the present invention basically consists of the above-mentioned fluoroalkyl sulfonium salt, but if necessary, other cations or acid generators may be used. A known cation or acid generator may be used in combination.
  • the cations or acid generators of the present invention are highly sensitive to these energy lines, and are less than conventional acid generators. A large amount of radiation can produce cations or acids.
  • the fluoroalkionium salt of the present invention salt-type cations or acid generators can be combined with sensitizers to produce The activity against the glow is further enhanced, and it can be used as an ultra-sensitive cation or acid generator.
  • the sensitizer include naphthene-lens conductor, enthracene-induced conductor, phenanthrene-induced conductor, pyrene-induced conductor, naphthene-induced conductor, and Condensed polycyclic aromatic conductors, such as relene conductors, pentyne conductors, hexacene conductors, heptacene conductors, etc., fluorene conductors, na Footquinone dielectric, anthraquinone dielectric, benzoin dielectric, xanthen dielectric, thioxanthen dielectric, xanthen dielectric , Chixanthon dielectric, coumalin dielectric, cyanin dielectric, melocyan
  • the cations or acid generators of the present invention are energy-line It can generate cations or acids by irradiation, and can be used in fields where the generated cations or acids are used.
  • a chemically amplified type that converts a resin containing a functional group into a soluble or insoluble form in a developer by using the generated cation or acid as a catalyst. It is useful as a cation or acid generator for resist materials.
  • the cation or acid generator of the present invention is formed by crosslinking or condensing the cation or acid generated as a resist resin with a developer or a developer. If a resin of a type that is insoluble in water is used, it becomes a chemically amplified negative resist material.
  • resist resins include, for example, cyclized isoprene-based negative resists and polyvinyl alcohol-based negative resists. Polyvinyl citrate-based negative resists, copolymers of polyester acrylate and hydroxystyrene, and the like. It is.
  • the resist resin is, for example, an alkali-soluble resin serving as a base resin, such as a nopolak resin; Enol resin; Polyisopropionyl phenol resin; Vinyl phenol and acrylic acid, methacrylic acid, acrylonitrile Lilyl, methyl methacrylate, methylyl acrylate, maleic acid, maleic anhydride, isopropenyl phenol, Copolymer with styrene or ⁇ -methylstyrene; isopropenyl phenol and acrylic acid, methacrylic acid, ac Rilonitrile, methyl methacrylate, methyl acrylate, maleic acid, anhydrous maleic acid, isopro ⁇ Nil phenol, steel
  • the positional relationship between the hydroxyl group and vinyl or isoprol group Is not particularly limited, but in general, P—vinylphenol or P—isopronylphenol is preferred.
  • These resins may be partially hydrogenated to improve the transparency.
  • an alkyl group, a hydroxyl group, etc. may be introduced into the phenol nucleus of the resin within a range that is soluble in the alkali.
  • polyvinyl phenol resin that is, a single polymer or vinyl phenol resin, is used. Copolymers of vinyl phenol with other monomers are preferred.
  • a group which is introduced into an alkali-soluble resin has a dissolution inhibiting property in an alkaline developer but is unstable to an acid
  • various known groups can be used.
  • Protecting groups can be employed. For example, tert—butoxycarbonyl, tert—butoxymethyl, 11-ethoxy, 1-methoxy , 1 _ Propoxethyl, 1-Isoproxethyl, 1 tert-Butoxycil, 1-Isobutoxylile, 1 _ Bu Tokichiru, 1-punch opening kit, 1-kro opening opening kit, 1_tok opening, 1-k opening Mouth mouth mouth, 1 — mouth mouth mouth, 1 — Cyclo mouth mouth, 1 mouthpiece or 1-medium Toxicity 11 Alkoxyalkyl groups such as methylethyl; tetrahydro 2-vinylanil, 6-methoxy Lahidlow 2 Vilanil, 6—Extra-Hydroxy 2—Vila Nile, Tetra-Hydrogen 2—
  • the cation or acid generator of the present invention is highly sensitive to energy rays.
  • the addition amount of cation or acid generator may be smaller than in the past.
  • 0.1 to 20 parts by weight, more preferably 0.1 to 10 parts by weight, with respect to 100 parts by weight of the resist resin is preferable.
  • the above-mentioned other acid generator and Z or a sensitizer may be used in combination.
  • an organic base compound is added as a quencher. It is known that the performance deterioration due to the deactivation of the acid due to the post-exposure pull-in can be improved, and this is also the case with the present invention. It is preferable to add an organic base compound.
  • the organic base compounds used herein include, for example, hexylamine, heptylamine, octylamine, nonylamine, and decylamine.
  • tertiary amides such as N, N-dimethylmethylanilinine; ethylenediamine, tetramethylenediamine or hexamidine; Diamines such as thiresamine; imidazole, pyridin, 4-methylpyridin, 4—methylimidazole or bipyridin; Unsaturated cyclic amines such as gin are produced. These organic base compounds can be used alone or in combination of two or more.
  • the degree of decomposition was determined by measuring 19 F-NMR.
  • the solution was transferred to a sample bottle using 1 ml of acetonitrile, and 8 ml of pure water was stirred with stirring, and one minute later, the pH was measured.
  • the measurement of the PH of the solution was started using the method, and the measurement was performed three times within two minutes, and the average value was obtained. Table 1 shows the results.
  • the fluoroalkylonium salt used in the present invention can be prepared by any of the various methods described in the above-mentioned known documents, or a combination of the various methods with various organic chemical methods. It can be synthesized in a new way.
  • Example 46 the fluoroalkyl kilonium salt synthesized in Example 46 is a novel compound.
  • the present invention it is possible to provide a cation or an acid generator with high sensitivity to energy rays.
  • this cation or acid generator is blended into the resist resin, the irradiation time of the energy beam can be reduced, thus shortening the irradiation time.
  • the resist processing can be performed only by irradiating high energy rays for a very short time, so that ultra-fine processing can be achieved.

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  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne un générateur de cations ou d'acides qui, lorsqu'il est irradié par des rayons d'énergie, peut générer des cations ou des acides à haute sensibilité. Ce générateur peut être particulièrement utilisé dans des matériaux de réserve de type à amplification chimique. Il comprend un sel de fluoroalkylonium sensible au rayons d'énergie, représenté par la formule (1), dans laquelle R1 à R3 (représentant chacun alkyle, aryle, etc.) et R¿f? (fluoroalkyle) sont liés à l'élément central A (iode, soufre, sélénium, tellure, azote, ou phosphore). En outre, cette invention concerne un matériau de réserve de type à amplification chimique contenant un générateur d'acides.
PCT/JP2001/001060 2000-03-13 2001-02-15 Cation de type sel de fluoroalkylonium ou generateur d'acides generant des cations ou des acides lorsqu'il est irradie par des rayons d'energie Ceased WO2001068575A1 (fr)

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JP2000-68241 2000-03-13
JP2000068241A JP2001255647A (ja) 2000-03-13 2000-03-13 エネルギー線照射によりカチオンまたは酸を発生するフルオロアルキルオニウム塩型のカチオンまたは酸発生剤

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WO2002039186A3 (fr) * 2000-11-09 2002-11-21 Du Pont Generateurs photoacides utilises dans des compositions de photoresist pour la microlithographie
WO2003040090A1 (fr) * 2001-11-06 2003-05-15 Wako Pure Chemical Industries, Ltd. Sel onium hybride
JP2004233661A (ja) * 2003-01-30 2004-08-19 Fuji Photo Film Co Ltd 感刺激性組成物及び化合物
JP2009040761A (ja) * 2007-07-18 2009-02-26 Tokyo Ohka Kogyo Co Ltd 新規な化合物およびその製造方法、酸発生剤、レジスト組成物およびレジストパターン形成方法

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JP4701231B2 (ja) * 2002-02-13 2011-06-15 富士フイルム株式会社 電子線、ｅｕｖ又はｘ線用ネガ型レジスト組成物及びそれを用いたパターン形成方法
JP2003302753A (ja) * 2002-04-11 2003-10-24 Matsushita Electric Ind Co Ltd パターン形成方法
JP4070538B2 (ja) * 2002-08-19 2008-04-02 富士フイルム株式会社 ネガ型レジスト組成物
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JP4677353B2 (ja) * 2005-02-18 2011-04-27 富士フイルム株式会社 レジスト組成物、該レジスト組成物に用いる化合物及び該レジスト組成物を用いたパターン形成方法
JP5366075B2 (ja) * 2008-11-18 2013-12-11 国立大学法人 名古屋工業大学 トリフルオロメチルチオフェニウム誘導体塩、その製造方法、その中間体並びにそれを用いたトリフルオロメチル基含有化合物類の製造方法
US8338076B2 (en) 2008-11-28 2012-12-25 Tokyo Ohka Kogyo Co., Ltd. Resist composition, method of forming resist pattern, novel compound, and acid generator
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WO2011013307A1 (fr) * 2009-07-28 2011-02-03 国立大学法人名古屋工業大学 Sels dérivés du trifluorométhylthiophénium, leur procédé de production et procédé de production de composés contenant du trifluorométhyle à l'aide de ces derniers
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CN119080661A (zh) * 2017-11-30 2024-12-06 罗门哈斯电子材料有限责任公司 两性离子化合物和包括其的光致抗蚀剂
JP6965232B2 (ja) * 2017-11-30 2021-11-10 ローム アンド ハース エレクトロニック マテリアルズ エルエルシーRohm and Haas Electronic Materials LLC 塩およびそれを含むフォトレジスト
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GB2273927A (en) * 1992-12-09 1994-07-06 Du Pont Sensitized onium salts
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002039186A3 (fr) * 2000-11-09 2002-11-21 Du Pont Generateurs photoacides utilises dans des compositions de photoresist pour la microlithographie
WO2003040090A1 (fr) * 2001-11-06 2003-05-15 Wako Pure Chemical Industries, Ltd. Sel onium hybride
CN100418947C (zh) * 2001-11-06 2008-09-17 和光纯药工业株式会社 杂化鎓盐
KR100902374B1 (ko) * 2001-11-06 2009-06-11 와코 쥰야꾸 고교 가부시키가이샤 하이브리드형 오늄염
JP2004233661A (ja) * 2003-01-30 2004-08-19 Fuji Photo Film Co Ltd 感刺激性組成物及び化合物
JP2009040761A (ja) * 2007-07-18 2009-02-26 Tokyo Ohka Kogyo Co Ltd 新規な化合物およびその製造方法、酸発生剤、レジスト組成物およびレジストパターン形成方法

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