WO2012133352A1 - Composition de résine photosensible - Google Patents

Composition de résine photosensible Download PDF

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Publication number
WO2012133352A1
WO2012133352A1 PCT/JP2012/057837 JP2012057837W WO2012133352A1 WO 2012133352 A1 WO2012133352 A1 WO 2012133352A1 JP 2012057837 W JP2012057837 W JP 2012057837W WO 2012133352 A1 WO2012133352 A1 WO 2012133352A1
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Prior art keywords
group
structural unit
carbon atoms
photoresist composition
polymer
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English (en)
Japanese (ja)
Inventor
一樹 笠原
憲彦 池田
浩光 中島
吉田　昌史
雅史 堀
龍一 芹澤
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JSR Corp
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JSR Corp
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Priority to JP2013507575A priority Critical patent/JP5862657B2/ja
Publication of WO2012133352A1 publication Critical patent/WO2012133352A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1812—C12-(meth)acrylate, e.g. lauryl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1806—C6-(meth)acrylate, e.g. (cyclo)hexyl (meth)acrylate or phenyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1808—C8-(meth)acrylate, e.g. isooctyl (meth)acrylate or 2-ethylhexyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1811—C10or C11-(Meth)acrylate, e.g. isodecyl (meth)acrylate, isobornyl (meth)acrylate or 2-naphthyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F224/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen
    • 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
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • 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
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
    • 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
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/11—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having cover layers or intermediate layers, e.g. subbing layers
    • 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
    • G03F7/20—Exposure; Apparatus therefor
    • G03F7/2041—Exposure; Apparatus therefor in the presence of a fluid, e.g. immersion; using fluid cooling means
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10P—GENERIC PROCESSES OR APPARATUS FOR THE MANUFACTURE OR TREATMENT OF DEVICES COVERED BY CLASS H10
    • H10P76/00—Manufacture or treatment of masks on semiconductor bodies, e.g. by lithography or photolithography

Definitions

  • the present invention relates to a photoresist composition.
  • photoresist compositions as a composition suitable for a shorter wavelength ArF excimer laser, for example, a composition containing a polymer containing an alicyclic group having no large absorption in the 193 nm region in the skeleton is used.
  • a composition suitable for a shorter wavelength ArF excimer laser for example, a composition containing a polymer containing an alicyclic group having no large absorption in the 193 nm region in the skeleton is used.
  • the polymer those having a spirolactone structure have been proposed (see JP 2002-82441 A and JP 2002-308937 A). It is said that such a polymer having a spirolactone structure can improve the development contrast of a photoresist composition containing the polymer.
  • the photoresist composition for forming a finer resist pattern has improved lithography performance using not only basic characteristics such as sensitivity and resolution but also MEEF, DOF, LWR, etc. as an index. Etc. are desired.
  • the present invention has been made based on the circumstances as described above, and its purpose is not only basic characteristics such as sensitivity, but also a photoresist composition that sufficiently satisfies lithography performance with MEEF, DOF, LWR, etc. as an index. Is to provide things.
  • One or more polymer components (hereinafter also referred to as “[A] polymer component”) having a structural unit (II) containing at least one structure selected from the group consisting of: and [B] acid generation
  • a photoresist composition containing a body is a hydrogen atom, a fluorine atom, a hydroxyl group, or a monovalent organic group having 1 to 20 carbon atoms.
  • R 2 and R 3 are each independently a hydrogen atom or a fluorine atom.
  • a hydroxyl group or a monovalent organic group having 1 to 20 carbon atoms, or R 2 and R 3 are bonded to each other to form a ring structure having 3 to 10 carbon atoms together with the carbon atom to which they are bonded.
  • A is an integer of 1 to 6.
  • R 4 and R 5 are each Independently, a hydrogen atom, a fluorine atom, a hydroxyl group or a monovalent organic group having 1 to 20 carbon atoms, or R 4 and R 5 are bonded to each other, and together with the carbon atom to which they are bonded, carbon A ring structure of formula 3 to 10 is formed, provided that one of the hydrogen atoms contained in the ring structure is Or all may be substituted.
  • the photoresist composition comprises [A] a polymer component having a structural unit (I) containing a lactone structure represented by the above formula (1) and a structural unit (II) containing a cyclic structure such as a cyclic carbonate. Since it contains, it is excellent in the lithography performance which used MEEF, LWR, DOF etc. as a parameter
  • the structural unit (II) is preferably a structural unit (II-1) represented by the following formula (2).
  • R 6 is a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group
  • R 7 is a hydrocarbon group having 1 to 10 carbon atoms
  • X is —O—, —COO—, —OCO—, or —NH—, where n is an integer of 0 to 10.
  • n is 2 or more, the plurality of R 6 and X may be the same or different.
  • R 8 is a single bond or a hydrocarbon group having 1 to 5 carbon atoms
  • R 9 is a cyclic organic group having at least one structure selected from the group consisting of a cyclic carbonate structure, a sultone structure, and a lactone structure. (However, some or all of the hydrogen atoms of R 7 to R 9 may be substituted.)
  • the photoresist composition is further improved in lithography performance using MEEF, LWR, DOF, etc. as an index.
  • the polymer component further has a structural unit (III) represented by the following formula (3).
  • R 10 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group.
  • R 11 to R 13 each independently represents an alkyl group having 1 to 4 carbon atoms, or a carbon atom.
  • R 11 and R 12 may be bonded to each other to form an alicyclic structure together with the carbon atom to which they are bonded. A part or all of hydrogen atoms of the group and the alicyclic group may be substituted.
  • the structural unit (III) represented by the above formula (3) has an acid dissociable group that is easily dissociated by the action of an acid generated from the [B] acid generator upon exposure, the photoresist composition [A]
  • the polymer component further has the structural unit (III), so that basic characteristics such as sensitivity can be sufficiently satisfied.
  • the cyclic organic group having the lactone structure represented by R 9 is a norbornane lactone group or a butyrolactone group, the cyclic organic group having the cyclic carbonate structure is an ethylene carbonate group, and the cyclic organic group having the sultone structure is norbornane.
  • a sultone group is preferred.
  • the content of the structural unit (I) in the polymer component is 5 mol% or more and 60 mol% or less, and the total content of the structural unit (I) and the structural unit (III) is 10 mol% or more and 80 It is preferable that it is below mol%.
  • the photoresist composition has MEEF, LWR, Lithographic performance using DOF or the like as an index can be particularly improved.
  • the content of the structural unit in the polymer component is determined by measuring the 13 C-NMR spectrum of the [A] polymer component, and from the area ratio of the peak corresponding to each structural unit in the obtained spectrum. It can obtain
  • the photoresist composition of the present invention contains a [A] polymer component having a structural unit (I) containing a lactone structure and a structural unit (II) containing a cyclic structure such as a cyclic carbonate. Therefore, in addition to basic characteristics such as sensitivity, the lithography performance using MEEF, LWR, DOF, etc. as an index is excellent. Therefore, a fine pattern can be formed with high accuracy by using the photoresist composition.
  • the photoresist composition contains a [A] polymer component and a [B] acid generator. Moreover, you may contain another component, unless the effect of this invention is impaired. Hereinafter, each component will be described in detail.
  • the polymer component is a structural unit (I) represented by the above formula (1) and a structural unit other than the structural unit (I) in the same or different polymers, and a cyclic carbonate structure,
  • the photoresist composition satisfies basic characteristics such as sensitivity and is excellent in MEEF, DOF, and LWR.
  • the [A] polymer component is a copolymer of a plurality of types of monomer compounds such as a monomer compound that provides the structural unit (I) and a monomer compound that provides the structural unit (II). Or two or more polymers obtained by blending a plurality of polymers such as a polymer of a monomer compound that gives the structural unit (I) and a polymer of the monomer compound that gives the structural unit (II).
  • the component may be included.
  • the structural unit (III) represented by the above formula (3) is preferably included. Furthermore, you may have another structural unit, unless the effect of this invention is impaired.
  • each structural unit will be described in detail.
  • the structural unit (I) is represented by the above formula (1). [A] Since the polymer component has a structural unit (I) containing a specific lactone structure directly connected to the polymer main chain, the photoresist composition is excellent in MEEF performance, DOF and LWR.
  • R 1 is a hydrogen atom, a fluorine atom, a hydroxyl group or a monovalent organic group having 1 to 20 carbon atoms.
  • R 2 and R 3 are each independently a hydrogen atom, a fluorine atom, a hydroxyl group, or a monovalent organic group having 1 to 20 carbon atoms, or R 2 and R 3 are bonded to each other and bonded A ring structure having 3 to 10 carbon atoms is formed together with the carbon atoms.
  • a is an integer of 1 to 6. However, when a is 2 or more, the plurality of R 2 and R 3 may be the same or different.
  • R 4 and R 5 are each independently a hydrogen atom, a fluorine atom, a hydroxyl group, or a monovalent organic group having 1 to 20 carbon atoms, or R 4 and R 5 are bonded to each other and bonded to each other.
  • a ring structure having 3 to 10 carbon atoms is formed together with the carbon atoms. However, one part or all part of the hydrogen atom which the said ring structure has may be substituted.
  • Examples of the monovalent organic group having 1 to 20 carbon atoms represented by R 1 to R 5 include a chain hydrocarbon group having 1 to 20 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, And an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heterocyclic group having 3 to 10 nuclear atoms, an epoxy group, a cyano group, a carboxy group, and a group represented by —R′—QR ′′.
  • R ′ is a single bond or a hydrocarbon group having 1 to 20 carbon atoms.
  • R ′′ is an optionally substituted hydrocarbon group having 1 to 20 carbon atoms.
  • Q is —O—, —CO—, —NH—, —SO 2 —, —SO— or a group formed by combining these.
  • halogen atoms such as fluorine atoms, cyano groups, carboxy groups, hydroxyl groups, thiol groups, etc. May be.
  • Examples of the chain hydrocarbon group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, an octyl group, and a decyl group.
  • a methyl group, an ethyl group, a propyl group, a butyl group and a pentyl group are preferable, and a methyl group and an ethyl group are more preferable.
  • Examples of the alicyclic hydrocarbon group having 3 to 20 carbon atoms include monocyclic alicyclic hydrocarbon groups such as cyclopropyl group, cyclobutyl group, cyclohexyl group, cyclooctyl group, and cyclodecyl group; norbornyl group And a polycyclic alicyclic hydrocarbon group such as an adamantyl group.
  • Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group and a naphthyl group.
  • heterocyclic group having 3 to 10 nuclear atoms examples include lactone group, cyclic carbonate group, sultone group, furyl group, thienyl group, benzofuryl group, benzothienyl group, dibenzofuryl group, dibenzothienyl group, pyridyl group and the like. Is mentioned. Among these, a lactone group, a cyclic carbonate group, and a sultone group are preferable, and a lactone group is more preferable.
  • Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by R ′ and R ′′ in —R′—QR ′′ include, for example, a chain hydrocarbon group having 1 to 20 carbon atoms, and 3 to 20 carbon atoms. And an alicyclic hydrocarbon group and an aromatic hydrocarbon group having 6 to 20 carbon atoms. For each, the same groups as those exemplified for the monovalent organic group having 1 to 20 carbon atoms represented by R 1 to R 5 can be given.
  • Examples of the ring structure having 3 to 10 carbon atoms formed together with the carbon atom to which R 2 and R 3 and R 4 and R 5 are bonded include cyclopropane, cyclohexane, norbornane, adamantane, etc. And a heterocyclic ring containing a hetero atom such as an oxygen atom, a sulfur atom, or a nitrogen atom.
  • cyclopentane, cyclohexane and adamantane are preferable as the alicyclic ring
  • cyclic ether, lactone and sultone are preferable as the heterocyclic ring.
  • substituents in which part or all of the hydrogen atoms in the ring structure may be substituted include, for example, a fluorine atom, a hydroxyl group, a carboxy group, a cyano group, a sulfanyl group, and a chain hydrocarbon having 1 to 20 carbon atoms.
  • a fluorine atom for example, a fluorine atom, a hydroxyl group, a carboxy group, a cyano group, a sulfanyl group, and a chain hydrocarbon having 1 to 20 carbon atoms.
  • R 2 and R 3 are preferably hydrogen atoms. Moreover, as said a, 1 is preferable.
  • Examples of the structural unit (I) include structural units represented by the following formulas (1-1) to (1-71).
  • At least one group of R 4 and R 5 are structural units, structural units in which at least one group of R 4 and R 5 is a cyclic organic group, R 4 and R 5 bonded to an oxygen atom And a structural unit forming a ring structure with the carbon atom to which they are bonded, a structural unit containing a hydroxyl group, and the like are preferable.
  • the above formulas (1-1) to (1-9), (1-12) to (1-21), (1-25) to (1-47), (1-55) to (1-67) ), (1-69) to (1-71) and the like are more preferred, and (1-1), (1-17), (1-19), (1-70) and (1) -71) is more preferred.
  • the content of the structural unit (I) is such that the total amount of the structural unit (I) is 1 mol% or more and 80 mol% or less with respect to all the structural units constituting the [A] polymer component. Is preferable, and more preferably 5 mol% or more and 60 mol% or less. By setting the content of the structural unit (I) in the above range, excellent lithography performance can be exhibited while maintaining other performance.
  • the [A] polymer component may have 1 type, or 2 or more types of structural units (I).
  • Examples of the monomer that gives the structural unit (I) include compounds represented by the following formulas.
  • the monomer giving the structural unit (I) can be produced, for example, by the following method.
  • the structural unit (II) is a structural unit other than the structural unit (I) and includes at least one structure selected from the group consisting of a cyclic carbonate structure, a sultone structure, and a lactone structure.
  • the said photoresist composition can improve MEEF performance, DOF, and LWR by containing the [A] polymer component which has structural unit (II).
  • the structural unit (II) is preferably a structural unit (II-1) represented by the above formula (2).
  • the photoresist composition can further improve MEEF performance, DOF, and LWR by containing the [A] polymer component having the structural unit (II-1) having the specific structure.
  • R 6 is a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group.
  • R 7 is a hydrocarbon group having 1 to 10 carbon atoms.
  • X is —O—, —COO—, —OCO— or —NH—.
  • n is an integer of 0 to 10. When n is 2 or more, the plurality of R 7 and X may be the same or different.
  • R 8 is a single bond or a hydrocarbon group having 1 to 5 carbon atoms.
  • R 9 is a cyclic organic group having at least one structure selected from the group consisting of a cyclic carbonate structure, a sultone structure, and a lactone structure. However, part or all of the hydrogen atoms of R 7 to R 9 may be substituted.
  • Examples of the hydrocarbon group having 1 to 10 carbon atoms represented by R 7 include a chain hydrocarbon group having 1 to 10 carbon atoms, an alicyclic hydrocarbon group having 3 to 10 carbon atoms, and 6 to 6 carbon atoms. 10 aromatic hydrocarbon groups and the like.
  • Examples of the chain hydrocarbon group having 1 to 10 carbon atoms include a methylene group, an ethylene group, and a propylene group. Of these, a methylene group and an ethylene group are preferred.
  • Examples of the alicyclic hydrocarbon group having 3 to 10 carbon atoms include a cyclopropylene group, a cyclohexylene group, and an adamantylene group. Of these, an adamantylene group is preferred.
  • Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms include a phenylene group and a naphthylene group.
  • X is preferably —O— or —COO—.
  • N is preferably an integer of 0 to 5, more preferably 0 and 1.
  • Examples of the hydrocarbon group having 1 to 5 carbon atoms represented by R 8 include a chain hydrocarbon group having 1 to 5 carbon atoms and an alicyclic hydrocarbon group having 3 to 5 carbon atoms.
  • Examples of the chain hydrocarbon group having 1 to 5 carbon atoms include a methylene group, an ethylene group, and a propylene group. Of these, a methylene group is preferred.
  • Examples of the alicyclic hydrocarbon group having 3 to 5 carbon atoms include a cyclopropylene group and a cyclobutylene group.
  • R 8 is preferably a single bond or a methylene group.
  • Examples of the cyclic organic group having a cyclic carbonate structure represented by R 9 include an ethylene carbonate group, a 1,3-propylene carbonate group, a cyclopentene carbonate group, a cyclohexene carbonate group, and a norbornene carbonate group.
  • Examples of the cyclic organic group having a sultone structure include a propiosluton group, a butyrosulton group, a valero sultone group, and an adamantane sultone group.
  • Examples of the cyclic organic group having the lactone structure include a propiolactone group, a butyrolactone group, a valerolactone group, an adamantane lactone group, and the like.
  • the cyclic organic group having a cyclic carbonate structure is preferably an ethylene carbonate group
  • the cyclic organic group having a sultone structure is preferably a norbornane sultone group
  • the cyclic organic group having a lactone structure is a norbornane lactone group.
  • a butyrolactone group are preferred.
  • Examples of the substituent in which part or all of the hydrogen atoms of R 7 to R 9 may be substituted include, for example, a halogen atom, a hydroxyl group, a carboxyl group, a keto group, a sulfonamide group, an amino group, an amide group, A cyano group, an acetyl group, etc. are mentioned.
  • structural unit (II) structural units represented by the following formulas (2-1) to (2-17) can be mentioned as preferred structural units.
  • R ⁇ 6 > is synonymous with the said Formula (2).
  • the content of the structural unit (II) is such that the total amount of the structural unit (II) with respect to all the structural units constituting the [A] polymer component is 5 mol% or more and 80 mol% or less. Preferably, 5 mol% or more and 60 mol% or less are more preferable. By making content of structural unit (II) into the said range, the outstanding lithography performance can be exhibited, maintaining another performance.
  • the [A] polymer component may have 1 type, or 2 or more types of structural units (II).
  • Examples of the monomer compound that gives the structural unit (II) include compounds represented by the following formulae.
  • the polymer component preferably has a structural unit (III).
  • the photoresist composition can sufficiently satisfy basic characteristics such as sensitivity, and can include MEEF, DOF and An excellent resist pattern can be formed by LWR.
  • R 10 is a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group.
  • R 11 to R 13 are each independently an alkyl group having 1 to 4 carbon atoms or an alicyclic group having 4 to 20 carbon atoms. However, R 11 and R 12 may be bonded to each other to form a divalent alicyclic structure together with the carbon atom to which they are bonded. Moreover, one part or all part of the hydrogen atom which the said alkyl group and alicyclic group have may be substituted.
  • Examples of the alkyl group having 1 to 4 carbon atoms represented by R 11 to R 13 include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, and a tert-butyl group. , 2-methylpropyl group, 1-methylpropyl group and the like.
  • Examples of the alicyclic group having 4 to 20 carbon atoms represented by R 11 to R 13 include a polycyclic alicyclic group having a bridged skeleton such as an adamantane skeleton and a norbornane skeleton; and a cycloaliphatic group such as cyclopentane and cyclohexane. And a monocyclic alicyclic group having an alkane skeleton. These groups may be substituted with one or more of linear, branched or cyclic alkyl groups having 1 to 10 carbon atoms, for example.
  • Examples of the aromatic hydrocarbon group having 6 to 20 carbon atoms represented by R 11 to R 13 include benzene, naphthalene, phenanthrene, anthracene, tetracene, pentacene, pyrene, picene, toluene, xylene, ethylbenzene, mesitylene, cumene and the like. And a group obtained by removing one hydrogen atom from an aromatic hydrocarbon group.
  • Examples of the alicyclic structure that R 11 and R 12 may be bonded to each other and formed together with the carbon atom to which they are bonded include polycyclic fatty acids having a bridged skeleton such as adamantane and norbornane. Examples thereof include a cyclic structure and a monocyclic alicyclic structure having a cycloalkane skeleton such as cyclopentane and cyclohexane.
  • the structural unit (III) is preferably a structural unit represented by the following formula.
  • R 10 has the same meaning as the above formula (3).
  • R 11 is an alkyl group having 1 to 4 carbon atoms.
  • m is an integer of 1 to 6.
  • more preferred structural units include structural units represented by the following formulas (3-1) to (3-22).
  • R 10 has the same meaning as the above formula (3).
  • the content of the structural unit (III) is preferably 10% by mole to 80% by mole, more preferably 15% by mole to 80% with respect to all structural units constituting the [A] polymer component. More preferred is mol%, and more preferred is 20 mol% to 70 mol%. By making the content rate of structural unit (III) into the said range, the lithography performance of the resist pattern obtained improves more.
  • the [A] polymer component may have 1 type, or 2 or more types of structural units (III).
  • Examples of the monomer that gives the structural unit (III) include monomers represented by the following formulas.
  • the polymer component may contain a structural unit having a hydrophilic functional group (hereinafter also referred to as “structural unit (IV)”).
  • structural unit (IV) a structural unit having a hydrophilic functional group
  • Examples of the structural unit (IV) include a structural unit represented by the following formula.
  • R 14 is a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group.
  • the content of the structural unit (IV) in the polymer component is preferably 0 mol% to 30 mol%, preferably 5 mol% to 20 mol%, based on all structural units constituting the [A] polymer component. Is more preferable.
  • the polymer component may have one or more structural units (IV).
  • the content of the structural unit (I) in the polymer component [A] is 1 mol% or more and 70 mol% or less, and
  • the total content of the structural unit (I) and the structural unit (III) is preferably from 10 mol% to 80 mol%, and the content of the structural unit (I) is from 5 mol% to 60 mol%. More preferably, the total content of the structural unit (I) and the structural unit (III) is 20 mol% or more and 70 mol% or less.
  • the content of the structural unit (I) is 10 mol% or more and 50 mol% or less, and the total content of the structural unit (I) and the structural unit (III) is 30 mol% or more and 60 mol% or less. Further preferred.
  • the weight average molecular weight of the polymer (i) having the structural unit (I) is the structural unit ( It is preferred that the polymer (ii) having II) is larger than the weight average molecular weight.
  • the polymer component [A] is a blend of the polymer (i) having the structural unit (I) and the polymer (ii) having the structural unit (II)
  • the weight average molecular weight of the polymer (i) is larger than the weight average molecular weight of the polymer (ii)
  • the lithography performance using MEEF, LWR or the like as an index is excellent.
  • the polymer component can be produced, for example, by polymerizing monomers corresponding to predetermined structural units in a suitable solvent using a radical polymerization initiator.
  • a method of dropping a solution containing a monomer and a radical initiator into a reaction solvent or a solution containing the monomer to cause a polymerization reaction, a solution containing the monomer, and a solution containing the radical initiator Separately, a method of dropping a reaction solvent or a monomer-containing solution into a polymerization reaction, a plurality of types of solutions containing each monomer, and a solution containing a radical initiator, It is preferable to synthesize by a method such as a method of dropping it into a reaction solvent or a solution containing a monomer to cause a polymerization reaction.
  • the reaction temperature in these methods may be appropriately determined depending on the initiator type. Usually, it is 30 ° C to 180 ° C, preferably 40 ° C to 160 ° C, and more preferably 50 ° C to 140 ° C.
  • the dropping time varies depending on the reaction temperature, the type of initiator, the monomer to be reacted, etc., but is usually 30 minutes to 8 hours, preferably 45 minutes to 6 hours, more preferably 1 hour to 5 hours. .
  • the total reaction time including the dropping time varies depending on the conditions as in the dropping time, but is usually from 30 minutes to 8 hours, preferably from 45 minutes to 7 hours, and more preferably from 1 hour to 6 hours.
  • radical initiator used in the polymerization examples include azobisisobutyronitrile, 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile), 2,2′-azobis (2-cyclopropyl). Propionitrile), 2,2′-azobis (2,4-dimethylvaleronitrile), 2,2′-azobis (2-methylpropionitrile), and the like. Two or more of these initiators may be mixed and used.
  • the polymerization solvent is not limited as long as it is a solvent other than a solvent that inhibits polymerization (nitrobenzene having a polymerization inhibiting effect, mercapto compound having a chain transfer effect, etc.) and can dissolve the monomer.
  • the polymerization solvent include alcohol solvents, ketone solvents, amide solvents, ester / lactone solvents, nitrile solvents, and mixed solvents thereof. These solvents can be used alone or in combination of two or more.
  • the resin obtained by the polymerization reaction is preferably recovered by a reprecipitation method. That is, after completion of the polymerization reaction, the target resin is recovered as a powder by introducing the polymerization solution into a reprecipitation solvent.
  • a reprecipitation solvent alcohols or alkanes can be used alone or in admixture of two or more.
  • the resin can be recovered by removing low-molecular components such as monomers and oligomers by a liquid separation operation, a column operation, an ultrafiltration operation, or the like.
  • polymer component is one polymer component having the structural unit (I) and the structural unit (II) in the same polymer
  • a monomer that gives the structural unit (I) and A monomer giving the structural unit (II) can be produced by copolymerization by the above-described method.
  • the polymer component is two or more polymer components having the structural unit (I) and the structural unit (II) in different polymers
  • a monomer that gives the structural unit (I) is used.
  • the polymer having the structural unit (I) is produced by polymerization by the above-described method, and the polymer having the structural unit (II) is produced by further polymerizing the monomer giving the structural unit (II) by the above-described method.
  • polymer component can be adjusted by mixing both.
  • the polystyrene-reduced weight average molecular weight (Mw) of the polymer component by gel permeation chromatography (GPC) is not particularly limited, but is preferably 1,000 or more and 500,000 or less, and preferably 2,000 or more and 400,000 or less. More preferred.
  • Mw of the [A] polymer is less than 1,000, the heat resistance when used as a resist tends to decrease.
  • Mw of the [A] polymer exceeds 500,000, the developability when used as a resist tends to be lowered.
  • the ratio (Mw / Mn) of Mw to polystyrene-converted number average molecular weight (Mn) by GPC of the polymer component is usually from 1 to 5, preferably from 1 to 3, preferably from 1 to 2. More preferred. By setting Mw / Mn in such a range, the photoresist film has excellent resolution performance.
  • polymer components are two or more polymer components having the structural unit (I) and the structural unit (II) in different polymers, Mw and Mw / About Mn, it is good in it being the same range as the above.
  • Mw and Mn in this specification are analyzed using GPC columns (Toso, G2000HXL, G3000HXL, G4000HXL), flow rate of 1.0 ml / min, elution solvent tetrahydrofuran, and column temperature of 40 ° C. It is a value measured by gel permeation chromatography (GPC) using monodisperse polystyrene as a standard under conditions.
  • GPC gel permeation chromatography
  • the acid generator is a compound that generates an acid by light passing through a mask in an exposure process, which is one process of forming a resist pattern.
  • the [B] acid generator in the photoresist composition, even in an embodiment of a compound as described later (hereinafter, this embodiment is also referred to as “[B] acid generator”), as a part of the polymer It may be a built-in embodiment or both of these embodiments.
  • Examples of the acid generator include onium salt compounds, sulfonimide compounds, halogen-containing compounds, diazoketone compounds, and the like. Of these [B] acid generators, onium salt compounds are preferred.
  • onium salt compounds examples include sulfonium salts (including tetrahydrothiophenium salts), iodonium salts, phosphonium salts, diazonium salts, pyridinium salts, and the like.
  • sulfonium salt examples include triphenylsulfonium trifluoromethanesulfonate, triphenylsulfonium nonafluoro-n-butanesulfonate, triphenylsulfonium perfluoro-n-octanesulfonate, triphenylsulfonium 2-bicyclo [2.2.1] hept.
  • triphenylsulfonium trifluoromethanesulfonate triphenylsulfonium nonafluoro-n-butanesulfonate, triphenylsulfonium 1,1-difluoro-2- (1-adamantyl) ethanesulfonate, triphenylsulfonium 1,1,2, 2-tetrafluoro-6- (1-adamantylcarbonyloxy) hexane-1-sulfonate, triphenylsulfonium 3- (2-oxa-3-oxo-1,7,7-trimethylbicyclo [2,2,1] Heptane-1-ylcarbonyloxy) -1,1,2-trifluoropropane-1-sulfonate, triphenylsulfonium 5- (norbornane lactonyloxycarbonyl-1,2-cyclohexanediylcarbonyloxy) -1,1,2, , 2-te
  • tetrahydrothiophenium salt examples include 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiophenium trifluoromethanesulfonate and 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiophenium.
  • Nonafluoro-n-butanesulfonate 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiophenium perfluoro-n-octanesulfonate, 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothio Phenium 2- (bicyclo [2.2.1] hept-2-yl) -1,1,2,2-tetrafluoroethanesulfonate, 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiofe 1,1,2-trifluoro-4- (1-adamantylcarbonyloxy) ) Butane-1-sulfonate, 1- (6-n-butoxynaphthalen-2-yl) tetrahydrothiophenium trifluoromethanesulfonate, 1- (6-n-butoxynaphthalen-2-yl) tetrahydrothiophenium nonafluoro -N
  • iodonium salt examples include diphenyliodonium trifluoromethanesulfonate, diphenyliodonium nonafluoro-n-butanesulfonate, diphenyliodonium perfluoro-n-octanesulfonate, diphenyliodonium 2-bicyclo [2.2.1] hept-2-yl.
  • sulfonimide compound examples include N- (trifluoromethanesulfonyloxy) bicyclo [2.2.1] hept-5-ene-2,3-dicarboximide, N- (nonafluoro-n-butanesulfonyloxy) bicyclo [2.2.1] Hept-5-ene-2,3-dicarboximide, N- (perfluoro-n-octanesulfonyloxy) bicyclo [2.2.1] hept-5-ene-2,3 -Dicarboximide, N- (2-bicyclo [2.2.1] hept-2-yl-1,1,2,2-tetrafluoroethanesulfonyloxy) bicyclo [2.2.1] hept-5 Examples include ene-2,3-dicarboximide. Of these sulfonimide compounds, N- (trifluoromethanesulfonyloxy) bicyclo [2.2.1] hept-5-ene-2,
  • [B] acid generators may be used alone or in combination of two or more.
  • the amount used when the acid generator is an “agent” is [A] 100 mass of the polymer component from the viewpoint of ensuring the sensitivity and lithography performance of the resist coating film formed from the photoresist composition. 0.01 parts by mass or more and 25 parts by mass or less is preferable, and 0.1 parts by mass or more and 20 parts by mass or less is more preferable.
  • ⁇ Other optional components Other optional components that may be contained in the photoresist composition include [C] acid diffusion control agent, [D] polymer containing fluorine atom, [E] additive, solvent, alicyclic skeleton containing Examples thereof include compounds, surfactants and sensitizers. Hereinafter, each component will be described in detail.
  • the photoresist composition preferably further contains a [C] acid diffusion controller.
  • This [C] acid diffusion control agent controls the diffusion phenomenon in the resist film of the acid generated from the [B] acid generator by exposure, and suppresses an undesirable chemical reaction in the non-exposed region.
  • the storage stability of the resulting photoresist composition is improved, the resolution as a resist is further improved, and from exposure to heat treatment after exposure.
  • a change in the line width of the resist pattern due to fluctuations in the holding time (PED) can be suppressed, and a composition having excellent process stability can be obtained.
  • a nitrogen-containing compound having an Nt-alkoxycarbonyl group is preferably used.
  • nitrogen-containing compounds such as tertiary amine compounds, quaternary ammonium hydroxide compounds, and other nitrogen-containing heterocyclic compounds are used as the [C] acid diffusion controller.
  • tertiary amine compounds include triethylamine, tri-n-propylamine, tri-n-butylamine, tri-n-pentylamine, tri-n-hexylamine, tri-n-heptylamine, tri-n-octyl.
  • Tri (cyclo) alkylamines such as amine, cyclohexyldimethylamine, dicyclohexylmethylamine, and tricyclohexylamine; Fragrances such as aniline, N-methylaniline, N, N-dimethylaniline, 2-methylaniline, 3-methylaniline, 4-methylaniline, 4-nitroaniline, 2,6-dimethylaniline, 2,6-diisopropylaniline Group amines; Alkanolamines such as triethanolamine, N, N-di (hydroxyethyl) aniline; N, N, N ′, N′-tetramethylethylenediamine, N, N, N ′, N′-tetrakis (2-hydroxypropyl) ethylenediamine, 1,3-bis [1- (4-aminophenyl) -1- Methylethyl] benzenetetramethylenediamine, bis (2-dimethylaminoethyl) ether, bis (2-dieth
  • Examples of the quaternary ammonium hydroxide compound include tetra-n-propylammonium hydroxide and tetra-n-butylammonium hydroxide.
  • an onium salt compound that decomposes by exposure and loses basicity as acid diffusion controllability can be used.
  • an onium salt compound include a sulfonium salt compound represented by the following formula (5-1) and an iodonium salt compound represented by the following formula (5-2).
  • R 15 to R 19 in the above formulas (5-1) and (5-2) are each independently a hydrogen atom, an alkyl group, an alkoxyl group, a hydroxyl group, or a halogen atom.
  • Anb ⁇ represents OH ⁇ , R 20 —COO ⁇ , R 20 —SO 3 — (wherein R 20 independently represents an alkyl group, an aryl group, or an alkanol group), or the following formula:
  • the anion represented by (6) is represented.
  • sulfonium salt compound and the iodonium salt compound include triphenylsulfonium hydroxide, triphenylsulfonium acetate, triphenylsulfonium salicylate, diphenyl-4-hydroxyphenylsulfonium hydroxide, diphenyl-4-hydroxyphenylsulfonium acetate.
  • Diphenyl-4-hydroxyphenylsulfonium salicylate bis (4-tert-butylphenyl) iodonium hydroxide, bis (4-tert-butylphenyl) iodonium acetate, bis (4-tert-butylphenyl) iodonium hydroxide, Bis (4-t-butylphenyl) iodonium acetate, bis (4-t-butylphenyl) iodonium salicylate, 4-t Butylphenyl-4-hydroxyphenyliodonium hydroxide, 4-t-butylphenyl-4-hydroxyphenyliodonium acetate, 4-t-butylphenyl-4-hydroxyphenyliodonium salicylate, bis (4-t-butylphenyl) Iodonium 10-camphorsulfonate, diphenyliodonium 10-camphorsulfonate, triphenylsulfonium 10-camphorsulfonate,
  • triphenylsulfonium salicylate triphenylsulfonium 10-camphorsulfonate
  • 4- cyclohexylsulfonylphenyldiphenylsulfonium 5,6-bis (2,2,2-trifluoroethyloxycarbonyl) bicyclo [2,2 , 1] heptane-2-sulfonate is preferred.
  • the acid diffusion controller can be used alone or in combination of two or more.
  • the content ratio of the acid diffusion controller is preferably 10 parts by mass or less, and more preferably 0.1 parts by mass or more and 8 parts by mass or less with respect to 100 parts by mass of the polymer component [A].
  • the amount used exceeds 10 parts by mass, the sensitivity as a resist tends to decrease.
  • the photoresist composition may further contain a polymer containing [D] fluorine atoms (hereinafter also referred to as “[D] polymer”).
  • [D] A polymer is a polymer containing a fluorine atom, and it is preferable that a fluorine atom content rate is higher than a [A] polymer component.
  • the photoresist composition contains the [D] polymer
  • the hydrophobicity of the resist film is improved, and even when immersion exposure is performed, the substance elution suppression is excellent, and the resist film, the immersion liquid,
  • the receding contact angle of the photoresist composition can be sufficiently increased, and when the scan exposure is performed at a high speed, water droplets do not remain, and the usefulness of the photoresist composition for immersion exposure increases.
  • [D] As an aspect of the polymer, for example, a structure in which a fluorinated alkyl group is bonded to the main chain; A structure in which a fluorinated alkyl group is bonded to the side chain; Examples include a structure in which a fluorinated alkyl group is bonded to the main chain and the side chain.
  • Monomers that give a structure in which a fluorinated alkyl group is bonded to the main chain include, for example, ⁇ -trifluoromethyl acrylate compounds, ⁇ -trifluoromethyl acrylate compounds, ⁇ , ⁇ -trifluoromethyl acrylate compounds, one or more types Examples thereof include compounds in which the hydrogen at the vinyl moiety is substituted with a fluorinated alkyl group such as a trifluoromethyl group.
  • Monomers that give a structure in which a fluorinated alkyl group is bonded to the side chain include, for example, those in which the side chain of an alicyclic olefin compound such as norbornene is a fluorinated alkyl group or a derivative thereof, acrylic acid or methacrylic acid side Examples thereof include ester compounds in which the chain is a fluorinated alkyl group or a derivative thereof, and one or more olefin side chains (parts not including a double bond) being a fluorinated alkyl group or a derivative thereof.
  • Monomers that give a structure in which a fluorinated alkyl group is bonded to the main chain and side chain include, for example, ⁇ -trifluoromethylacrylic acid, ⁇ -trifluoromethylacrylic acid, ⁇ , ⁇ -trifluoromethylacrylic acid, etc.
  • One or more vinyl moiety hydrogens are substituted with a fluorinated alkyl group such as a trifluoromethyl group.
  • the hydrogen bonded to the double bond of one or more alicyclic olefin compounds is replaced with a fluorinated alkyl group such as a trifluoromethyl group, and the side chain is a fluorinated alkyl group or a derivative thereof. And the like.
  • an alicyclic olefin compound shows the compound in which a part of ring is a double bond.
  • the polymer preferably has a structural unit (d1) represented by the following formula (7) and / or a structural unit (d2) represented by the formula (8), and the structural unit (d1) and You may have "another structural unit” other than a structural unit (d2).
  • a structural unit (d1) represented by the following formula (7) and / or a structural unit (d2) represented by the formula (8)
  • the structural unit (d1) and You may have "another structural unit” other than a structural unit (d2).
  • each structural unit will be described in detail.
  • the structural unit (d1) is a structural unit represented by the following formula (7).
  • R 21 is a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group.
  • R 22 is a C 1-6 alkyl group having a fluorine atom, or a C 4-20 monovalent alicyclic hydrocarbon group having a fluorine atom. However, in the alkyl group and alicyclic hydrocarbon group, part or all of the hydrogen atoms may be substituted.
  • Examples of the monomer that gives the structural unit (d1) include trifluoromethyl (meth) acrylate, 2,2,2-trifluoroethyl (meth) acrylate, perfluoroethyl (meth) acrylate, perfluoro n-propyl ( (Meth) acrylate, perfluoro i-propyl (meth) acrylate, perfluoro n-butyl (meth) acrylate, perfluoro i-butyl (meth) acrylate, perfluoro t-butyl (meth) acrylate, perfluorocyclohexyl (meth) Acrylate, 2- (1,1,1,3,3,3-hexafluoro) propyl (meth) acrylate, 1- (2,2,3,3,4,4,5,5-octafluoro) pentyl ( (Meth) acrylate, 1- (2,2,3,3,4,4,5,5-octafluoro) he Sil (me
  • Examples of the structural unit (d1) include structural units represented by the following formulas (7-1) and (7-2).
  • R 21 has the same meaning as in the above formula (7).
  • the content of the structural unit (d1) is preferably 10 mol% to 70 mol%, more preferably 20 mol% to 50 mol%, based on all structural units constituting the [D] polymer. More preferred.
  • the polymer may have one or more structural units (d1).
  • the structural unit (d2) is a structural unit represented by the following formula (8).
  • R 23 is a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group.
  • R 24 is a (k + 1) -valent linking group.
  • Y is a divalent linking group having a fluorine atom.
  • R 25 is a hydrogen atom or a monovalent organic group. k is an integer of 1 to 3. However, when k is 2 or 3, the plurality of Y and R 25 may be the same or different.
  • Examples of the structural unit (d2) include structural units represented by the following formulas (8-1) and (8-2).
  • R 24 is a divalent linear, branched or cyclic saturated or unsaturated hydrocarbon group having 1 to 20 carbon atoms.
  • R 23 , Y and R 25 are as defined in the above formula (8).
  • R 23 , Y, R 25 and k are as defined in the above formula (8). However, when k is 2 or 3, the plurality of Y and R 25 may be the same or different.
  • Examples of the structural units represented by the above formulas (8-1) and (8-2) include the following formulas (8-1-1), (8-1-2), and (8-2-1): ).
  • R 23 has the same meaning as in the above formula (8).
  • Examples of the monomer that gives the structural unit (d2) include (meth) acrylic acid (1,1,1-trifluoro-2-trifluoromethyl-2-hydroxy-3-propyl) ester and (meth) acrylic acid. (1,1,1-trifluoro-2-trifluoromethyl-2-hydroxy-4-butyl) ester, (meth) acrylic acid (1,1,1-trifluoro-2-trifluoromethyl-2-hydroxy -5-pentyl) ester, (meth) acrylic acid (1,1,1-trifluoro-2-trifluoromethyl-2-hydroxy-4-pentyl) ester, (meth) acrylic acid 2- ⁇ [5- ( 1 ′, 1 ′, 1′-trifluoro-2′-trifluoromethyl-2′-hydroxy) propyl] bicyclo [2.2.1] heptyl ⁇ ester and the like.
  • the content of the structural unit (d2) is preferably 20% by mole to 80% by mole, more preferably 30% by mole to 70% by mole, based on all the structural units constituting the [D] polymer. More preferred.
  • the [D] polymer may have 1 type, or 2 or more types of structural units (d2).
  • the polymer further includes, as “other structural units”, a structural unit having a lactone structure, a cyclic carbonate structure or a sultone structure in order to increase solubility in a developer, and an alicyclic structure in order to increase etching resistance.
  • other structural units a structural unit having a lactone structure, a cyclic carbonate structure or a sultone structure in order to increase solubility in a developer, and an alicyclic structure in order to increase etching resistance.
  • One or more structural units may be included.
  • Examples of the structural unit having a lactone structure, a cyclic carbonate structure, or a sultone structure include the same structural units as those exemplified as the structural unit (II) of the above-mentioned [A] polymer component.
  • Examples of the structural unit including an alicyclic structure include a structural unit represented by the following formula (9).
  • R 26 represents a hydrogen atom, a fluorine atom, a methyl group or a trifluoromethyl group.
  • Y 2 is an alicyclic hydrocarbon group having 4 to 20 carbon atoms.
  • Examples of the monomer that gives a structural unit containing an alicyclic compound include (meth) acrylic acid-bicyclo [2.2.1] hept-2-yl ester and (meth) acrylic acid-bicyclo [2.2. 2] Oct-2-yl ester, (meth) acrylic acid-tricyclo [5.2.1.0 2,6 ] dec-7-yl ester, (meth) acrylic acid-tricyclo [3.3.1.1] 3,7 ] dec-1-yl ester, (meth) acrylic acid-tricyclo [3.3.1.1 3,7 ] dec-2-yl ester, and the like.
  • the structural unit (d1), the structural unit (d2), and other structural units may have only one kind of each structural unit, or may contain two or more kinds.
  • the polymer does not contain a unit having an aromatic group.
  • an ArF light source when used, it may cause a decrease in sensitivity. Further, when developing with a negative developer, the shape may deteriorate.
  • the content of the polymer is preferably 1 part by mass to 15 parts by mass, and more preferably 2 parts by mass to 10 parts by mass with respect to 100 parts by mass of the polymer component [A].
  • the polymer can be produced, for example, by polymerizing a monomer corresponding to each predetermined structural unit in a suitable solvent using a radical polymerization initiator.
  • a polymerization initiator a solvent, etc. which are used for the synthesis
  • the reaction temperature in the above polymerization is usually preferably 40 ° C to 150 ° C and 50 ° C to 120 ° C.
  • the reaction time is usually preferably 1 hour to 48 hours and 1 hour to 24 hours.
  • the weight average molecular weight (Mw) in terms of polystyrene by gel permeation chromatography (GPC) of the polymer is preferably 1,000 to 50,000, more preferably 1,000 to 30,000, and 1,000. ⁇ 10,000 is particularly preferred.
  • Mw weight average molecular weight
  • GPC gel permeation chromatography
  • the ratio (Mw / Mn) between the Mw of the polymer and the polystyrene-equivalent number average molecular weight (Mn) by the GPC method is usually 1 to 3, preferably 1 to 2.
  • the photoresist composition may contain an [E] additive when a resist pattern is formed using an immersion exposure method.
  • Examples of the [E] additive that may be contained in the photoresist composition include ⁇ -butyrolactone, propylene carbonate, and the like. Of these, ⁇ -butyrolactone is preferred.
  • the photoresist composition usually contains a solvent.
  • the solvent is not particularly limited as long as it can dissolve at least the [A] polymer component, the [B] acid generator and other components.
  • As the solvent alcohol solvents, ether solvents, ketone organic solvents, amide solvents, ester organic solvents, hydrocarbon solvents and the like can be used.
  • alcohol solvents include methanol, ethanol, n-propanol, i-propanol, n-butanol, i-butanol, sec-butanol, tert-butanol, n-pentanol, i-pentanol, 2-methylbutanol, sec-pentanol, tert-pentanol, 3-methoxybutanol, n-hexanol, 2-methylpentanol, sec-hexanol, 2-ethylbutanol, sec-heptanol, 3-heptanol, n-octanol, 2-ethylhexanol , Sec-octanol, n-nonyl alcohol, 2,6-dimethyl-4-heptanol, n-decanol, sec-undecyl alcohol, trimethylnonyl alcohol, sec-tetradecyl alcohol, sec-hept
  • ether solvent examples include diethyl ether, dipropyl ether, dibutyl ether, diphenyl ether and the like.
  • ketone solvent examples include acetone, methyl ethyl ketone, methyl-n-propyl ketone, methyl-n-butyl ketone, diethyl ketone, methyl-i-butyl ketone, methyl-n-pentyl ketone, ethyl-n-butyl ketone, methyl-n- And ketone solvents such as hexyl ketone, di-i-butyl ketone, trimethylnonanone, cyclopentanone, cyclohexanone, cycloheptanone, cyclooctanone, methylcyclohexanone, 2,4-pentanedione, acetonylacetone, acetophenone, etc. .
  • amide solvents include N, N′-dimethylimidazolidinone, N-methylformamide, N, N-dimethylformamide, N, N-diethylformamide, acetamide, N-methylacetamide, N, N-dimethylacetamide, Examples thereof include N-methylpropionamide and N-methylpyrrolidone.
  • ester solvents include diethyl carbonate, propylene carbonate, methyl acetate, ethyl acetate, ⁇ -butyrolactone, ⁇ -valerolactone, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate, sec sec -Butyl, n-pentyl acetate, sec-pentyl acetate, 3-methoxybutyl acetate, methyl pentyl acetate, 2-ethylbutyl acetate, 2-ethylhexyl acetate, benzyl acetate, cyclohexyl acetate, methyl cyclohexyl acetate, n-nonyl acetate, acetoacetic acid Methyl, ethyl acetoacetate, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether a
  • hydrocarbon solvent examples include n-pentane, i-pentane, n-hexane, i-hexane, n-heptane, i-heptane, 2,2,4-trimethylpentane, n-octane, i-octane and cyclohexane.
  • Aliphatic hydrocarbon solvents such as methylcyclohexane; Fragrances such as benzene, toluene, xylene, mesitylene, ethylbenzene, trimethylbenzene, methylethylbenzene, n-propylbenzene, i-propylbenzene, diethylbenzene, i-butylbenzene, triethylbenzene, di-i-propylbenzene, n-amylnaphthalene Group hydrocarbon solvents and the like.
  • Fragrances such as benzene, toluene, xylene, mesitylene, ethylbenzene, trimethylbenzene, methylethylbenzene, n-propylbenzene, i-propylbenzene, diethylbenzene, i-butylbenzene, triethylbenzene, di-i-propyl
  • ester solvents and ketone solvents are preferable, and propylene glycol monomethyl ether acetate and cyclohexanone are more preferable.
  • These organic solvents may be used alone or in combination of two or more.
  • An alicyclic skeleton compound is a component that exhibits an action of further improving dry etching resistance, pattern shape, adhesion to a substrate, and the like.
  • Examples of the alicyclic skeleton compound include adamantane derivatives such as 1-adamantanecarboxylic acid, 2-adamantanone, and 1-adamantanecarboxylic acid t-butyl; deoxycholic acid t-butyl, deoxycholic acid t-butoxycarbonylmethyl, Deoxycholic acid esters such as 2-ethoxyethyl deoxycholate; Lithocholic acid esters such as tert-butyl lithocholic acid, t-butoxycarbonylmethyl lithocholic acid, 2-ethoxyethyl lithocholic acid; 3- [2-hydroxy-2 , 2-Bis (trifluoromethyl) ethyl] tetracyclo [4.4.0.1 2,5 . 1 7,10 ] dodecane
  • Surfactants are components that have the effect of improving coatability, striation, developability, and the like.
  • examples of the surfactant include polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, polyoxyethylene oleyl ether, polyoxyethylene n-octylphenyl ether, polyoxyethylene n-nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol diacrylate.
  • nonionic surfactants such as stearate
  • the following trade names are KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), Polyflow No. 75, no.
  • the sensitizer absorbs radiation energy and transmits the energy to the [C] acid generator, thereby increasing the amount of acid generated. It has the effect of improving the “sensitivity”.
  • the sensitizer include carbazoles, acetophenones, benzophenones, naphthalenes, phenols, biacetyl, eosin, rose bengal, pyrenes, anthracenes, phenothiazines and the like.
  • the photoresist composition can be prepared, for example, by mixing the [A] polymer component, the [B] acid generator and other optional components in a predetermined ratio in the solvent.
  • the photoresist composition is usually dissolved in a solvent so that the total solid content is 1% by mass to 30% by mass, preferably 1.5% by mass to 25% by mass. It is prepared by filtering with a filter of about 2 ⁇ m.
  • step (1) a step of forming a coating film of the photoresist composition on a substrate
  • step (2) A step of irradiating at least a part of the coating film
  • step (3) a step of developing the coating film irradiated with the radiation
  • a resist pattern excellent in MEEF, LWR and DOF can be formed using the photoresist composition. Accordingly, even with radiation such as KrF excimer laser, ArF excimer laser, EUV, etc., it is possible to form a fine pattern from the photoresist composition with high accuracy and stability, and further miniaturization is expected in the future. It can be suitably used for manufacturing semiconductor devices.
  • a photoresist composition or a solution of the photoresist composition obtained by dissolving the photoresist composition in a solvent is applied to a silicon wafer, silicon dioxide, reflection, or the like by a coating means such as spin coating, cast coating, or roll coating. It is applied to a substrate such as a wafer coated with a protective film so as to have a predetermined film thickness.
  • the solvent in the coating film is usually baked (SB) at a temperature of about 70 ° C. to 160 ° C. Volatilizes to form a resist film.
  • Step (2) the resist film formed in the step (1) is exposed by irradiation with radiation (in some cases through an immersion medium such as water). At this time, radiation is irradiated through a mask having a predetermined pattern.
  • the radiation is appropriately selected from visible light, ultraviolet light, far ultraviolet light, X-rays, charged particle beams, EUV, etc. according to the line width of the target pattern.
  • far ultraviolet rays represented by ArF excimer laser (wavelength 193 nm) and KrF excimer laser (wavelength 248 nm) are preferable, and light sources capable of forming finer patterns such as EUV (extreme ultraviolet ray, wavelength 13.5 nm) are preferred.
  • PEB post-exposure baking
  • a resist pattern is formed by developing the exposed resist film with a developer. After development, it is common to wash with water and dry.
  • the developer include sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, aqueous ammonia, ethylamine, n-propylamine, diethylamine, di-n-propylamine, triethylamine, methyldiethylamine, ethyl Dimethylamine, triethanolamine, tetramethylammonium hydroxide, tetrabutylammonium hydroxide, pyrrole, piperidine, choline, 1,8-diazabicyclo- [5.4.0] -7-undecene, 1,5-diazabicyclo- [ 4.3.0]
  • An aqueous alkali solution in which at least one alkaline compound such as 5-nonene is dissolved is preferable.
  • an immersion liquid insoluble immersion protective film is formed on the resist film.
  • the immersion protective film include a solvent-peeling protective film that peels off with a solvent before the step (3) (see, for example, JP-A-2006-227632), and a developer that peels off simultaneously with the development in the step (3). Any of peelable protective films (for example, see International Publication No. 2005-069096, International Publication No. 2006-035790, etc.) may be used.
  • the weight average molecular weight (Mw) and number average molecular weight (Mn) are GPC columns manufactured by Tosoh Corporation (2 G2000HXL, 1 G3000HXL, 1 G4000HXL), flow rate: 1.0 mL / min, elution solvent: tetrahydrofuran, column temperature. : Measured by gel permeation chromatography (GPC) using monodisperse polystyrene as a standard under analysis conditions of 40 ° C. The degree of dispersion (Mw / Mn) was calculated from the measurement results of Mw and Mn.
  • GPC gel permeation chromatography
  • the structural unit derived from the monomer in the polymer was analyzed using JNM-ECX400 manufactured by JEOL Ltd. and deuterated chloroform as a measurement solvent.
  • the content of the structural unit in the polymer can be determined as an average value in the polymer from the area ratio of peaks corresponding to each structural unit in the obtained spectrum by measuring the 13 C-NMR spectrum of the polymer.
  • the polymerization solution was cooled with water and cooled to 30 ° C. or lower.
  • the cooled polymerization solution was put into 800 g of methanol, and the precipitated white powder was separated by filtration.
  • the filtered white powder was washed twice with 160 g of methanol, filtered, and dried at 50 ° C. for 17 hours to obtain a white powdery polymer component (A-1) (30 g, yield 75%). ).
  • Mw of the obtained polymer component (A-1) was 4000, and Mw / Mn was 1.4.
  • the content of the structural unit derived from the compound (M-1): the structural unit derived from the compound (Ss-1): the structural unit derived from the compound (L-1) was 46:23 : 31 (mol%).
  • the polymerization solution was cooled with water and cooled to 30 ° C. or lower.
  • the cooled polymerization solution was put into 800 g of methanol, and the precipitated white powder was separated by filtration.
  • the filtered white powder was washed twice with 160 g of methanol, then filtered and dried at 50 ° C. for 17 hours to obtain a white powdery polymer (36 g, yield 90%).
  • a polymer was obtained in the same manner as above except that 22.8 g (50 mol%) of compound (L-1) was used instead of 20 g (50 mol%) of compound (Ss-1).
  • the above two types of polymers were mixed at a molar ratio of 1: 1 to obtain a polymer component (A-20).
  • the physical properties of the two types of polymers are shown in Table 1.
  • a polymer component (A-21) was obtained in the same manner as in Synthesis Example 20, except that a predetermined amount of the monomers listed in Table 1 were blended.
  • Table 1 shows the Mw, Mw / Mn, yield (%), and the content of the structural unit derived from each monomer in each polymer.
  • the polymerization solution was cooled with water and cooled to 30 ° C. or lower.
  • the filtered white powder was washed twice with 120 g of methanol, filtered and dried at 50 ° C. for 17 hours to obtain a white powdery polymer component (D-1) (20 g, 67% yield). ).
  • Mw of the obtained polymer (D-1) was 4,200, and Mw / Mn was 1.4.
  • the content of the structural unit derived from the compound (M-1): the structural unit derived from the compound (Ss-1): the structural unit derived from the compound (L-1) was 48.5. : 51.5 (mol%).
  • Polymer component (A-1) 100 parts by mass, acid generator (B-1) 10 parts by mass, acid diffusion controller (C-3) 2 parts by mass, (C-4) 3 parts by mass, polymer (D -1) 4 parts by mass, 30 parts by mass of ⁇ -butyrolactone as additive (E-1), 1,750 parts by mass of solvent (F-1) and 750 parts by mass of (F-2) were mixed, and the resulting mixture
  • the solution was filtered through a filter having a pore size of 0.2 ⁇ m to prepare a photoresist composition.
  • Examples 2 to 21 and Comparative Examples 1 to 9 A photoresist composition was prepared in the same manner as in Example 1 except that each type and amount of components shown in Table 3 were used.
  • each photoresist composition was post-exposure baked (PEB) at 95 ° C. for 60 seconds. Thereafter, the resist film was developed with a 2.38 mass% tetramethylammonium hydroxide aqueous solution, washed with water, and dried to form a positive resist pattern.
  • an exposure amount at which a portion exposed through a mask pattern for forming a pattern of 50 nm Line 100 nm Pitch forms a Line having a line width of 50 nm was defined as an optimum exposure amount (Eop).
  • This optimum exposure amount was defined as sensitivity (mJ / cm 2 ).
  • a scanning electron microscope Hitachi High-Technologies Corporation, CG4000
  • the sensitivity was 40 (mJ / cm 2 ) or less, it was evaluated as good.
  • MEEF A positive resist pattern was formed by the same method as in the sensitivity (mJ / cm 2 ) evaluation, and Eop was measured.
  • LS patterns were formed through mask patterns for forming patterns of 48 nm line 100 nm, 49 nm line 100 nm pitch, 50 nm line 100 nm pitch, 51 nm line 100 nm pitch, and 52 nm line 100 nm pitch, respectively.
  • the slope of the straight line when the line size (nm) of the mask was plotted on the horizontal axis and the line width (nm) formed on the resist film using each mask pattern was plotted on the vertical axis was calculated as MEEF.
  • the MEEF straight line
  • LWR (nm) A positive resist pattern was formed by the same method as in the sensitivity (mJ / cm 2 ) evaluation, and Eop was measured. A line having a line width of 50 nm formed by the Eop was observed from above the pattern, and the line width was measured at any 10 points. The 3-sigma value (variation) of the measured line width was defined as LWR (nm). If the value of this LWR was 5.4 nm or less, it was evaluated that the formed pattern shape was good.
  • DOF (nm) The focus swing when the pattern size resolved by the 50 nm line and space pattern mask is within ⁇ 10% of the mask design dimension at the optimum exposure (Eop) in the sensitivity evaluation. was DOF (nm).
  • the photoresist composition of the present invention was excellent in sensitivity, MEEF, DOF, and LWR lithography performances.
  • the photoresist composition of the present invention is suitably used in the formation of resist patterns in the lithography process of various electronic devices such as semiconductor devices and liquid crystal devices.

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Abstract

La présente invention a pour objet une composition de résine photosensible qui possède des propriétés essentielles, telles que la sensibilité, et qui présente d'excellentes performances lithographiques, comme le MEEF, la DOF et la LWR. Cette composition de résine photosensible comprend : [A] un ou plusieurs types de composants polymères ayant, dans des polymères identiques ou différents, une unité structurale (I) représentée par la formule (1), ainsi qu'une unité structurale (II) différente de l'unité structurale (I) et comportant au moins un type de structure sélectionné dans le groupe constitué par des structures de carbonate cyclique, des structures de sultone et des structures de lactone; et [B] un générateur d'acide.
PCT/JP2012/057837 2011-03-31 2012-03-26 Composition de résine photosensible Ceased WO2012133352A1 (fr)

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JP2013114085A (ja) * 2011-11-29 2013-06-10 Fujifilm Corp 感活性光線性又は感放射線性樹脂組成物、並びに、該組成物を用いたレジスト膜、パターン形成方法、電子デバイスの製造方法及び電子デバイス
JP2013117693A (ja) * 2011-12-05 2013-06-13 Fujifilm Corp 感活性光線性又は感放射線性樹脂組成物、並びに、該組成物を用いたレジスト膜、パターン形成方法、電子デバイスの製造方法及び電子デバイス
JP2013190637A (ja) * 2012-03-14 2013-09-26 Tokyo Ohka Kogyo Co Ltd 溶剤現像ネガ型レジスト組成物、レジストパターン形成方法
JP2013205837A (ja) * 2012-03-29 2013-10-07 Jsr Corp フォトレジスト組成物及びレジストパターン形成方法
US20130280657A1 (en) * 2012-04-02 2013-10-24 Jsr Corporation Photoresist composition and resist pattern-forming method
JP2014077999A (ja) * 2012-09-21 2014-05-01 Sumitomo Chemical Co Ltd 樹脂、レジスト組成物及びレジストパターンの製造方法
WO2014185288A1 (fr) * 2013-05-14 2014-11-20 富士フイルム株式会社 Composition de resine photosensible a la lumiere active ou radiosensible et procede de formation de motifs utilisant cette dernière
JP2014224991A (ja) * 2013-04-18 2014-12-04 住友化学株式会社 レジスト組成物及びレジストパターンの製造方法
WO2015037520A1 (fr) * 2013-09-12 2015-03-19 Jsr株式会社 Composition de résine, procédé de formation de motif de réserve et polymère
WO2017065207A1 (fr) * 2015-10-16 2017-04-20 東京応化工業株式会社 Composition de résine photosensible et procédé de formation de motif de résine photosensible
JP2017201427A (ja) * 2017-07-28 2017-11-09 東京応化工業株式会社 レジスト組成物及びレジストパターン形成方法
JP2018097125A (ja) * 2016-12-12 2018-06-21 Jsr株式会社 感放射線性樹脂組成物及びレジストパターン形成方法

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JP2013114085A (ja) * 2011-11-29 2013-06-10 Fujifilm Corp 感活性光線性又は感放射線性樹脂組成物、並びに、該組成物を用いたレジスト膜、パターン形成方法、電子デバイスの製造方法及び電子デバイス
JP2013117693A (ja) * 2011-12-05 2013-06-13 Fujifilm Corp 感活性光線性又は感放射線性樹脂組成物、並びに、該組成物を用いたレジスト膜、パターン形成方法、電子デバイスの製造方法及び電子デバイス
JP2013190637A (ja) * 2012-03-14 2013-09-26 Tokyo Ohka Kogyo Co Ltd 溶剤現像ネガ型レジスト組成物、レジストパターン形成方法
JP2013205837A (ja) * 2012-03-29 2013-10-07 Jsr Corp フォトレジスト組成物及びレジストパターン形成方法
US20130280657A1 (en) * 2012-04-02 2013-10-24 Jsr Corporation Photoresist composition and resist pattern-forming method
US9329474B2 (en) * 2012-04-02 2016-05-03 Jsr Corporation Photoresist composition and resist pattern-forming method
JP2014077999A (ja) * 2012-09-21 2014-05-01 Sumitomo Chemical Co Ltd 樹脂、レジスト組成物及びレジストパターンの製造方法
JP2014224991A (ja) * 2013-04-18 2014-12-04 住友化学株式会社 レジスト組成物及びレジストパターンの製造方法
JP2014222338A (ja) * 2013-05-14 2014-11-27 富士フイルム株式会社 感活性光線性又は感放射線性樹脂組成物、及びそれを用いたパターン形成方法
WO2014185288A1 (fr) * 2013-05-14 2014-11-20 富士フイルム株式会社 Composition de resine photosensible a la lumiere active ou radiosensible et procede de formation de motifs utilisant cette dernière
WO2015037520A1 (fr) * 2013-09-12 2015-03-19 Jsr株式会社 Composition de résine, procédé de formation de motif de réserve et polymère
JPWO2015037520A1 (ja) * 2013-09-12 2017-03-02 Jsr株式会社 樹脂組成物、レジストパターン形成方法及び重合体
US10331031B2 (en) 2013-09-12 2019-06-25 Jsr Corporation Resin composition, resist pattern-forming method and polymer
WO2017065207A1 (fr) * 2015-10-16 2017-04-20 東京応化工業株式会社 Composition de résine photosensible et procédé de formation de motif de résine photosensible
JPWO2017065207A1 (ja) * 2015-10-16 2018-08-02 東京応化工業株式会社 レジスト組成物およびレジストパターン形成方法
US11150554B2 (en) 2015-10-16 2021-10-19 Tokyo Ohka Kogyo Co., Ltd. Resist composition and method of forming resist pattern
JP2018097125A (ja) * 2016-12-12 2018-06-21 Jsr株式会社 感放射線性樹脂組成物及びレジストパターン形成方法
JP7062874B2 (ja) 2016-12-12 2022-05-09 Jsr株式会社 感放射線性樹脂組成物及びレジストパターン形成方法
JP2017201427A (ja) * 2017-07-28 2017-11-09 東京応化工業株式会社 レジスト組成物及びレジストパターン形成方法

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