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WO2018159356A1 - Composition pour formation de film contenant du silicium, film contenant du silicium, procédé de formation de motif et polysiloxane - Google Patents

Composition pour formation de film contenant du silicium, film contenant du silicium, procédé de formation de motif et polysiloxane Download PDF

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Publication number
WO2018159356A1
WO2018159356A1 PCT/JP2018/005724 JP2018005724W WO2018159356A1 WO 2018159356 A1 WO2018159356 A1 WO 2018159356A1 JP 2018005724 W JP2018005724 W JP 2018005724W WO 2018159356 A1 WO2018159356 A1 WO 2018159356A1
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group
silicon
containing film
carbon atoms
forming
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Japanese (ja)
Inventor
裕介 大坪
俊輔 栗田
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JSR Corp
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JSR Corp
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/28—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen sulfur-containing groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • 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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor

Definitions

  • the present invention relates to a silicon-containing film forming composition, a silicon-containing film, a pattern forming method, and polysiloxane.
  • a resist film is exposed and developed on a substrate to be processed via an organic antireflection film and a silicon-containing film, and etching is performed using the obtained resist pattern as a mask.
  • the process is heavily used.
  • problems such as collapse of resist patterns and reduction in etching selectivity of mask patterns.
  • studies have been made on silicon-containing film materials that improve the resist pattern collapse and mask pattern etching selectivity, and methods for forming patterns on substrates using such silicon-containing film materials. (See JP 2004-310019 A and International Publication No. 2012/039337).
  • the above conventional silicon-containing film cannot satisfy these requirements.
  • the substrate to be processed is damaged when the silicon-containing film is removed by plasma etching with a fluorine-based gas after the silicon-containing film pattern is formed using the resist pattern as a mask. Improvement in the removability of the contained film is also required.
  • the invention made to solve the above problems is a silicon-containing film-forming composition containing a polysiloxane having a group represented by the following formula (1) and a solvent.
  • L is a single bond or an (n + 1) -valent organic group having 1 to 20 carbon atoms.
  • E is a group represented by the following formula (2-1) or (2-2).
  • N is an integer of 1 to 3.
  • n is 2 or more, L is an organic group, and a plurality of E are the same or different, * is a site bonded to a silicon atom in the polysiloxane. Is shown.
  • R 1 is a single bond or a divalent organic group having 1 to 20 carbon atoms.
  • Y 1 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or at least 1 A monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms in which one hydrogen atom is substituted with an electron withdrawing group.
  • R 2 is a monovalent organic group having 1 to 20 carbon atoms.
  • Y 2 is a substituted or unsubstituted arenediyl group having 6 to 20 carbon atoms or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms in which at least one hydrogen atom is substituted with an electron withdrawing group.
  • Another invention made to solve the above problems is a silicon-containing film formed from the silicon-containing film-forming composition.
  • Still another invention made in order to solve the above-mentioned problems is a step of forming a silicon-containing film on the upper side of the substrate by coating the silicon-containing film-forming composition, and a step of forming a pattern on the silicon-containing film Is a pattern forming method.
  • Still another invention made to solve the above problems is a polysiloxane having a group represented by the above formula (1).
  • the composition for forming a silicon-containing film and the pattern forming method of the present invention it is possible to form a silicon-containing film that is excellent in resist pattern collapse suppression while maintaining the etching removability with a fluorine-based gas. It is possible to form a silicon-containing film that is excellent in resistance to an alkaline developer in the resist pattern forming step and excellent in releasability with alkaline hydrogen peroxide. Furthermore, the silicon-containing film forming composition of the present invention is excellent in storage stability. The silicon-containing film of the present invention is excellent in resist pattern collapse suppression while maintaining etching removability by a fluorine-based gas, and is excellent in resistance to an alkaline developer in the resist pattern forming process, and is also highly alkaline.
  • the polysiloxane of the present invention can be suitably used as a polysiloxane component of the silicon-containing film forming composition. Therefore, these can be used suitably for a multilayer resist process, and can be used suitably for manufacture of a semiconductor device etc. which are expected to be further miniaturized in the future.
  • the silicon-containing film forming composition includes a polysiloxane having a group represented by the formula (1) (hereinafter also referred to as “[A] polysiloxane”) and a solvent (hereinafter also referred to as “[B] solvent”). ) And.
  • the silicon-containing film-forming composition may contain an optional component as long as the effects of the present invention are not impaired. Hereinafter, each component will be described.
  • the polysiloxane is a polysiloxane having a group represented by the following formula (1) (hereinafter also referred to as “group (I)”).
  • L is a single bond or an (n + 1) -valent organic group having 1 to 20 carbon atoms.
  • E is a group represented by the following formula (2-1) or (2-2) (hereinafter also referred to as “group (II-1) or (II-2)”).
  • n is an integer of 1 to 3.
  • L is an organic group, and a plurality of E are the same or different. * Shows the site
  • R 1 is a single bond or a divalent organic group having 1 to 20 carbon atoms.
  • Y 1 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms in which at least one hydrogen atom is substituted with an electron withdrawing group.
  • R 2 is a monovalent organic group having 1 to 20 carbon atoms.
  • Y 2 is a substituted or unsubstituted arenediyl group having 6 to 20 carbon atoms or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms in which at least one hydrogen atom is substituted with an electron withdrawing group.
  • the silicon-containing film-forming composition contains [A] polysiloxane and [B] solvent, so that it retains etching removability with a fluorine-based gas and is excellent in resist pattern collapse suppression, A silicon-containing film having excellent resistance to an alkaline developer in the resist pattern forming step and excellent peelability with alkaline hydrogen peroxide can be formed, and storage stability is also excellent.
  • the reason why the composition for forming a silicon-containing film has the above-described configuration and thus achieves the above effect is not necessarily clear, but can be inferred as follows, for example.
  • [A] polysiloxane has a group (I) containing a sulfonate structure to which an electron withdrawing group or the like is bonded. Since this sulfonic acid ester structure has an electron-attracting group or the like bonded thereto, it is difficult to cleave even when heated at room temperature. Therefore, the silicon-containing film-forming composition is excellent in storage stability, and the formed silicon-containing film is excellent in resistance to an alkaline developer. Moreover, since this sulfone ester structure is cleaved by alkaline hydrogen peroxide and a sulfo group is generated, the silicon-containing film is excellent in releasability by alkaline hydrogen peroxide.
  • the (n + 1) -valent organic group having 1 to 20 carbon atoms represented by L in the above formula (1) includes an (n + 1) -valent hydrocarbon group having 1 to 20 carbon atoms, and the carbon-carbon of this hydrocarbon group A group ( ⁇ ) containing a divalent heteroatom-containing group in between, a group obtained by substituting part or all of the hydrogen atoms of the hydrocarbon group and the group ( ⁇ ) with a monovalent heteroatom-containing group, and the like It is done.
  • Examples of the (n + 1) -valent hydrocarbon group having 1 to 20 carbon atoms include an (n + 1) -valent chain hydrocarbon group having 1 to 20 carbon atoms and an (n + 1) -valent alicyclic carbon group having 3 to 20 carbon atoms. Examples thereof include a hydrogen group and an (n + 1) -valent aromatic hydrocarbon group having 6 to 20 carbon atoms.
  • Examples of the (n + 1) -valent chain hydrocarbon group having 1 to 20 carbon atoms include alkanes such as methane, ethane, propane, and butane, alkenes such as ethene, propene, and butene, and alkynes such as ethyne, propyne, and butyne. And a group in which 2 to 4 hydrogen atoms are removed.
  • Examples of the (n + 1) valent alicyclic hydrocarbon group having 3 to 20 carbon atoms include cycloalkanes such as cyclopentane and cyclohexane, alicyclic rings such as bridged ring saturated hydrocarbons such as norbornane, adamantane, and tricyclodecane.
  • alicyclic unsaturated hydrocarbons such as cycloalkenes such as saturated hydrocarbons, cyclopentenes, cyclohexenes and the like, bridged ring unsaturated hydrocarbons such as norbornene and tricyclodecene, etc., are removed from 2 to 4 hydrogen atoms Etc.
  • Examples of the (n + 1) -valent aromatic hydrocarbon group having 6 to 20 carbon atoms include 2 to 4 aromatic rings contained in an arene such as benzene, toluene, ethylbenzene, xylene, naphthalene, methylnaphthalene, anthracene, and methylanthracene.
  • Examples include a hydrogen atom on the above or a group on which 2 to 4 aromatic rings and an alkyl group are removed.
  • hetero atom constituting the divalent and monovalent hetero atom-containing group examples include an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, a silicon atom, and a halogen atom.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • divalent heteroatom-containing group examples include —O—, —CO—, —S—, —CS—, —NR′—, a group in which two or more of these are combined, and the like.
  • R ' is a hydrogen atom or a monovalent hydrocarbon group. Of these, —O— and —S— are preferred.
  • Examples of the monovalent heteroatom-containing group include halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom, hydroxy group, carboxy group, cyano group, amino group and sulfanyl group. Among these, a halogen atom is preferable, and a fluorine atom is more preferable.
  • n in the above formula (1) 1 and 2 are preferable, and 1 is more preferable.
  • L is preferably an (n + 1) -valent hydrocarbon group and a group containing a divalent heteroatom-containing group between carbon-carbons of this hydrocarbon group, and is an (n + 1) -valent chain hydrocarbon group or aromatic carbon group.
  • a hydrogen group and a group containing a divalent heteroatom-containing group between carbon-carbons of these hydrocarbon groups are more preferable.
  • L is more preferably an alkanediyl group, a group containing —O— or —S— between the carbon-carbon of the alkanediyl group, and an arenediyl group.
  • L is a group containing a divalent heteroatom-containing group between carbon-carbon of the hydrocarbon group, the etching removability of the silicon-containing film with a fluorine-based gas can be further enhanced.
  • Examples of the divalent organic group having 1 to 20 carbon atoms represented by R 1 in the formula (2-1) include those in which n is 1 among those exemplified as the (n + 1) valent organic group of L above. Etc.
  • R 1 is preferably a single bond.
  • Examples of the aryl group in the substituted or unsubstituted aryl group having 6 to 20 carbon atoms represented by Y 1 in the above formula (2-1) include, for example, a phenyl group, a benzyl group, a tolyl group, a xylyl group, a naphthyl group, an anthryl group. Groups and the like.
  • Examples of the substituent for the aryl group of Y 1 include a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, a hydroxy group, a cyano group, a nitro group, an acyl group, an acyloxy group, a hydrocarbon group, and an oxycarbonization.
  • a hydrogen group etc. are mentioned.
  • a halogen atom, a cyano group, a nitro group, an acyl group, and an acyloxy group are preferable from the viewpoint of electron withdrawing property, a halogen atom is more preferable, and a fluorine atom is more preferable.
  • Examples of the substituted or unsubstituted aryl group having 6 to 20 carbon atoms of Y 1 include a phenyl group, a naphthyl group, an anthryl group, a fluorophenyl group, a chlorophenyl group, a trifluorophenyl group, a pentafluorophenyl group, a fluorobenzyl group, and A difluorobenzyl group is preferred, a phenyl group, a fluorophenyl group and a fluorobenzyl group are more preferred, and a phenyl group and a fluorophenyl group are more preferred.
  • electron withdrawing an electron withdrawing group
  • Examples of the aliphatic hydrocarbon group in (also referred to as “substituent group-substituted aliphatic hydrocarbon group”) include, for example, the above-mentioned (1 + 1) -valent chain hydrocarbon group having 1 to 20 carbon atoms and (n + 1) carbon atoms having 3 to 20 carbon atoms. )
  • the valent alicyclic hydrocarbon group a group in which one hydrogen atom is added to a divalent group in which n is 1 can be mentioned.
  • Examples of the electron withdrawing group in the Y 1 electron withdrawing group-substituted aliphatic hydrocarbon group include a halogen atom, a cyano group, a nitro group, a halogenated hydrocarbon group having 1 to 10 carbon atoms, and a carbon number of 1 to 10 A group having —O—, a group having —SO— having 1 to 10 carbon atoms, a group having —SO 2 — having 1 to 10 carbon atoms, a group having —CO— having 1 to 10 carbon atoms, And groups having 1 to 10 —COO—.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • halogenated hydrocarbon group having 1 to 10 carbon atoms examples include monovalent groups such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a trichloromethyl group, a trifluoroethyl group, a hexafluoro i-propyl group, And halogenated chain hydrocarbon groups such as pentafluoro n-propyl group and nonafluoro n-butyl group.
  • Examples of the group having —O— having 1 to 10 carbon atoms include monovalent groups such as oxy hydrocarbon groups such as methoxy group, cyclohexyloxy group, and phenoxy group, hydroxy aromatic hydrocarbon groups such as hydroxyphenyl group, Examples thereof include cyclic ether groups such as a tetrahydrofuranyl group and a tetrahydropyranyl group.
  • Examples of the group having —SO— having 1 to 10 carbon atoms include monovalent groups such as a sulfoxy hydrocarbon group such as a methylsulfoxy group and a phenylsulfoxy group, and a cyclic sulfoxy group such as an S-oxotetrahydrothiophenyl group. Etc.
  • Examples of the group having 1 to 10 carbon atoms —SO 2 — include monovalent groups such as sulfonyl hydrocarbon groups such as methylsulfonyl group and phenylsulfonyl group, and cyclic sulfonyl groups such as S-dioxotetrahydrothiophenyl group. Etc.
  • Examples of the group having -CO- having 1 to 10 carbon atoms include monovalent groups such as acyl groups such as formyl group, acetyl group and benzoyl group, cyclic ketone groups such as oxocyclohexyl group and oxoadamantyl group. It is done.
  • Examples of the group having 1 to 10 carbon atoms —COO— include monovalent groups such as acyloxy groups such as formyloxy group, acetoxy group and benzoyloxy group, and carbonyloxy hydrocarbons such as methoxycarbonyl group and phenoxycarbonyl group. And a group having a lactone structure such as a butyrolactone-yl group and a norbornanelactone-yl group.
  • Examples of the electron withdrawing group include a monovalent group such as a halogen atom, a cyano group, a halogenated hydrocarbon group having 1 to 10 carbon atoms, a group having —O— having 1 to 10 carbon atoms, and 1 to 10 carbon atoms.
  • a group having —SO—, a group having 1 to 10 carbon atoms —SO 2 —, a group having 1 to 10 carbon atoms —CO—, and a group having 1 to 10 carbon atoms —COO— are preferred, More preferred are a fluorine atom, a chlorine atom, a cyano group, a fluorinated hydrocarbon group, an oxyhydrocarbon group, an acyl group, a carbonyloxy hydrocarbon group and a sulfonyl hydrocarbon group, a fluorine atom, a chlorine atom, a cyano group, a fluorinated alkyl group.
  • an alkoxy group, an alkylcarbonyl group, an alkoxycarbonyl group and an alkylsulfonyl group, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a methoxy group, an acetyl group, Group, methoxycarbonyl group and methylsulfonyl group is particularly preferred.
  • the silicon-containing film formed from [A] polysiloxane is a resist pattern formed on the upper side thereof, particularly a positive electrode formed by alkali development. It is considered that the adhesion between the mold and the resist pattern is further improved, and the resist pattern collapse prevention property is further improved.
  • the polysiloxane contains a fluorine atom, the etching removability by the fluorine-based gas is further improved.
  • the sensitivity of the radiation sensitive resin composition in the case of using extreme ultraviolet rays (EUV) can be increased.
  • EUV extreme ultraviolet rays
  • Examples of the electron-withdrawing group-substituted aliphatic hydrocarbon group for Y 1 include a group represented by the following formula (4-1).
  • R 4 to R 8 are each independently a hydrogen atom, a monovalent hydrocarbon group having 1 to 18 carbon atoms, or a monovalent electron withdrawing group.
  • p is 0 or 1. However, when p is 0, at least one of R 6 to R 8 is an electron withdrawing group. When p is 1, at least one of R 4 to R 8 is an electron withdrawing group.
  • R 4 to R 8 are preferably a hydrogen atom, a methyl group, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a methoxy group, a methoxycarbonyl group, a methylsulfonyl group, and an acetoxy group.
  • Y 1 is preferably an electron-withdrawing group-substituted aliphatic hydrocarbon group.
  • Group (II-2) As the monovalent organic group having 1 to 20 carbon atoms represented by R 2 in the above formula (2-2), for example, among those exemplified as the (n + 1) valent organic group of L, n is 1. And a group obtained by adding one hydrogen atom to a divalent organic group.
  • a monovalent hydrocarbon group is preferable, a monovalent chain hydrocarbon group is more preferable, an alkyl group is further preferable, and a methyl group and an ethyl group are particularly preferable.
  • Examples of the arenediyl group in the substituted or unsubstituted arenediyl group represented by Y 2 in the above formula (2-2) include benzenediyl group, toluenediyl group, xylenediyl group, naphthalene A diyl group, an anthracene diyl group, etc. are mentioned. Of these, a benzenediyl group is preferred.
  • Examples of the substituent of the above arenediyl group of Y 2 include those exemplified as the substituent of the aryl group of Y 1 . Among these, a halogen atom is preferable and a fluorine atom is more preferable.
  • Examples of the electron-withdrawing group-substituted aliphatic hydrocarbon group for Y 2 include a group represented by the following formula (4-2).
  • R 9 to R 12 are each independently a hydrogen atom, a monovalent hydrocarbon group having 1 to 18 carbon atoms, or a monovalent electron withdrawing group.
  • R 13 is a single bond, a divalent hydrocarbon group having 1 to 18 carbon atoms, or a divalent electron withdrawing group.
  • q is 0 or 1. However, when q is 0, at least one of R 11 to R 13 is an electron withdrawing group. When q is 1, at least one of R 9 to R 13 is an electron withdrawing group. ** represents a site bonded to —O— in the above formula (2-2).
  • R 9 to R 12 are preferably a hydrogen atom, a methyl group, a fluorine atom, a chlorine atom, a trifluoromethyl group, a cyano group, a methoxy group, a methoxycarbonyl group, a methylsulfonyl group, and an acetoxy group.
  • R 13 is preferably a single bond.
  • Q is preferably 1.
  • Y 2 is preferably a substituted or unsubstituted arenediyl group, more preferably a substituted or unsubstituted benzenediyl group, and even more preferably a benzenediyl group and a fluorobenzenediyl group.
  • the polysiloxane has a first structural unit represented by the formula (3) containing the group (I) (hereinafter also referred to as “structural unit (I)”).
  • structural unit (I) the polysiloxane includes a second structural unit represented by the formula (5) described later (hereinafter also referred to as “structural unit (II)”) and / or a formula (6) described later. 3) (hereinafter also referred to as “structural unit (III)”), and other than the structural units (I) to (III), as long as the effects of the present invention are not impaired.
  • structural unit (III) structural unit
  • the structural unit (I) is a structural unit represented by the following formula (3).
  • the composition for forming a silicon-containing film has the [A] polysiloxane having the structural unit (I), so that it is resistant to an alkaline developer, resist pattern is prevented from being collapsed, peelable by alkaline hydrogen peroxide, and stored. Stability can be further improved.
  • Z is said group (I).
  • R 3 is a monovalent organic group having 1 to 20 carbon atoms, a hydrogen atom or a hydroxy group that does not contain —SO 2 O—.
  • m is an integer of 0-2. When m is 2, two R 3 are the same or different.
  • Examples of the monovalent organic group having 1 to 20 carbon atoms that does not include —SO 2 O— represented by R 3 include, for example, a monovalent organic group having 1 to 20 carbon atoms in R 2 of the above formula (2-2). Examples thereof include those similar to the organic group.
  • R 3 is preferably an alkoxy group or a hydroxy group.
  • M is preferably 0 or 1, more preferably 0.
  • Examples of the monomer that gives the structural unit (I) include compounds represented by the following formulas (i-1-1) to (i-1-18) having the group (II-1) (hereinafter, It is assumed that “compounds (i-1-1) to (i-1-18)” have a group represented by the group (II-2) and the following formulas (i-2-1) to ( i-2-3) (hereinafter also referred to as “compounds (i-2-1) to (i-2-3)”) and the like.
  • R represents a monovalent hydrocarbon group having 1 to 20 carbon atoms. It is.
  • the hydrocarbon group for R is preferably an alkyl group, more preferably a methyl group or an ethyl group.
  • the lower limit of the content ratio of the structural unit (I) is preferably 0.1 mol%, more preferably 1 mol%, still more preferably 2 mol%, based on all structural units constituting the [A] polysiloxane. 5 mol% is particularly preferred, and 8 mol% is even more particularly preferred. As an upper limit of the said content rate, 80 mol% is preferable, 50 mol% is more preferable, 30 mol% is further more preferable, 20 mol% is especially preferable.
  • the composition for forming a silicon-containing film makes the content ratio of the structural unit (I) within the above range, so that it is resistant to an alkali developer, resist pattern collapse prevention, peelability by alkaline hydrogen peroxide, and storage stability. The property can be further improved.
  • the structural unit (II) is a structural unit represented by the following formula (5).
  • the etching resistance of the silicon-containing film with an oxygen-based gas can be further improved because [A] polysiloxane has the structural unit (II).
  • Examples of the monomer that gives the structural unit (II) include tetraalkoxysilanes such as tetramethoxysilane and tetraethoxysilane, and tetrahalosilanes such as tetrachlorosilane and tetrabromosilane.
  • the lower limit of the content ratio of the structural unit (II) is preferably 1 mol% with respect to all the structural units constituting the [A] polysiloxane. More preferably, mol% is more preferable, 30 mol% is further more preferable, and 60 mol% is especially preferable. As an upper limit of the said content rate, 95 mol% is preferable, 90 mol% is more preferable, 85 mol% is further more preferable, 80 mol% is especially preferable.
  • the composition for forming a silicon-containing film can further enhance the resistance of the silicon-containing film to an alkali developer and the etching resistance with an oxygen-based gas by setting the content ratio of the structural unit (II) in the above range.
  • the structural unit (III) is a structural unit represented by the following formula (6).
  • the said silicon-containing film formation composition can adjust the various characteristics of a silicon-containing film because [A] polysiloxane has structural unit (III).
  • R A is a monovalent organic group having 1 to 20 carbon atoms that does not contain —SO 2 O—.
  • a is 1 or 2.
  • two RA are the same or different.
  • Examples of the monovalent organic group having 1 to 20 carbon atoms that does not include —SO 2 O— represented by R A include monovalent organic groups having 1 to 20 carbon atoms of R 2 in the above formula (2-2). Examples are the same as those described above. Among these, a hydrocarbon group is preferable, a chain hydrocarbon group and an aromatic hydrocarbon group are more preferable, an alkyl group and an aryl group are further preferable, and a methyl group, an ethyl group, a phenyl group, and a naphthyl group are particularly preferable.
  • A is preferably 1.
  • Examples of the monomer that gives the structural unit (III) include methyltrimethoxysilane, phenyltriethoxysilane, dimethyldimethoxysilane, diphenyldiethoxysilane, methylphenyldimethoxysilane, cyclohexyltrichlorosilane, and the like.
  • the lower limit of the content ratio of the structural unit (III) is preferably 0.1 mol% with respect to all the structural units constituting the [A] polysiloxane. 1 mol% is more preferable, 8 mol% is further more preferable, and 12 mol% is especially preferable. As an upper limit of the said content rate, 80 mol% is preferable, 50 mol% is more preferable, 40 mol% is further more preferable, 25 mol% is further especially preferable.
  • the polysiloxane may have structural units other than the structural units (I) to (III) as other structural units as long as the effects of the present invention are not impaired.
  • Examples of other structural units include structural units derived from silane monomers containing a plurality of silicon atoms, such as hexamethoxydisilane, bis (trimethoxysilyl) methane, polydimethoxymethylcarbosilane, and the like.
  • the upper limit of the content ratio of the other structural units is preferably 10 mol%, preferably 5 mol% with respect to all structural units constituting the [A] polysiloxane. Is more preferable, 2 mol% is more preferable, and 5 mol% is particularly preferable.
  • the lower limit of the content of polysiloxane is preferably 50% by mass, more preferably 80% by mass, still more preferably 90% by mass, based on the total solid content of the silicon-containing film-forming composition. Mass% is particularly preferred. As an upper limit of the said content, 100 mass% is preferable, 99 mass% is preferable, and 97 mass% is more preferable.
  • the total solid content of the silicon-containing film forming composition refers to the sum of components other than [B] solvent. [A] Only 1 type of polysiloxane may be contained and 2 or more types may be contained.
  • the lower limit of the weight average molecular weight (Mw) of the polysiloxane is preferably 1,000, more preferably 1,300, still more preferably 1,500, and particularly preferably 1,700.
  • the upper limit of Mw is preferably 100,000, more preferably 20,000, still more preferably 7,000, and particularly preferably 3,000.
  • the Mw of [A] polysiloxane in this specification uses Tosoh's GPC columns (two “G2000HXL”, one “G3000HXL” and one “G4000HXL”), flow rate: 1.0 mL / min, elution It is a value measured by gel permeation chromatography (detector: differential refractometer) using monodisperse polystyrene under the analysis conditions of solvent: tetrahydrofuran, column temperature: 40 ° C.
  • Polysiloxane can be obtained by a method of hydrolyzing and condensing a hydrolyzable silane monomer corresponding to each structural unit described above. It is considered that each hydrolyzable silane monomer is incorporated into the polysiloxane regardless of the type by the hydrolytic condensation reaction, and the structural units (I) to (III) and other structural units in the synthesized [A] polysiloxane
  • the content ratio of is usually equivalent to the ratio of the amount of each monomer compound used in the synthesis reaction.
  • the silicon-containing film-forming composition contains a [B] solvent.
  • the solvent include alcohol solvents, ketone solvents, ether solvents, ester solvents, nitrogen-containing solvents, water, and the like.
  • a solvent can be used individually by 1 type or in combination of 2 or more types.
  • the alcohol solvent examples include monoalcohol solvents such as methanol, ethanol, n-propanol, iso-propanol, n-butanol and iso-butanol, ethylene glycol, 1,2-propylene glycol, diethylene glycol, dipropylene glycol and the like.
  • monoalcohol solvents such as methanol, ethanol, n-propanol, iso-propanol, n-butanol and iso-butanol, ethylene glycol, 1,2-propylene glycol, diethylene glycol, dipropylene glycol and the like.
  • polyhydric alcohol solvents examples include polyhydric alcohol solvents.
  • ketone solvents include acetone, methyl ethyl ketone, methyl-n-propyl ketone, methyl-iso-butyl ketone, and cyclohexanone.
  • ether solvents include ethyl ether, iso-propyl ether, ethylene glycol dibutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol diethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, Tetrahydrofuran etc. are mentioned.
  • ester solvent examples include ethyl acetate, ⁇ -butyrolactone, n-butyl acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, acetic acid
  • Examples include propylene glycol monoethyl ether, dipropylene glycol monomethyl ether acetate, dipropylene glycol monoethyl ether acetate, ethyl propionate, n-butyl propionate, methyl lactate, and ethyl lactate.
  • nitrogen-containing solvent examples include N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like.
  • ether solvents and ester solvents are preferable, and ether solvents and ester solvents having a glycol structure are more preferable because of excellent film-forming properties.
  • ether solvents and ester solvents having a glycol structure examples include propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl acetate
  • examples include ether. Among these, propylene glycol monomethyl ether acetate is particularly preferable.
  • the lower limit of the content of the ether solvent and the ester solvent having a glycol structure in the solvent is preferably 20% by mass, more preferably 60% by mass, still more preferably 90% by mass, and particularly preferably 100% by mass. preferable.
  • the lower limit of the content of the [B] solvent in the silicon-containing film-forming composition is preferably 80% by mass, more preferably 90% by mass, and still more preferably 95% by mass.
  • 99 mass% is preferable and 98 mass% is more preferable.
  • the silicon-containing film-forming composition may contain optional components such as a basic compound and an acid generator.
  • Examples of the basic compound include a compound having a basic amino group and a compound (base generator) that becomes a compound having a basic amino group by the action of an acid or the action of heat. More specifically, an amine compound, an amide group-containing compound as a base generator, a urea compound, a nitrogen-containing heterocyclic compound, and the like can be given.
  • the silicon-containing film-forming composition contains a base compound, curing of the silicon-containing film-forming composition can be promoted, and the resulting silicon-containing film can be more peelable from an acidic liquid. Can be increased.
  • Examples of the amine compound include mono (cyclo) alkylamines, di (cyclo) alkylamines, tri (cyclo) alkylamines, substituted alkylanilines or derivatives thereof, ethylenediamine, N, N, N ′, N′— Tetramethylethylenediamine, tetramethylenediamine, hexamethylenediamine, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl ether, 4,4'-diaminobenzophenone, 4,4'-diaminodiphenylamine, 2,2-bis ( 4-aminophenyl) propane, 2- (3-aminophenyl) -2- (4-aminophenyl) propane, 2- (4-aminophenyl) -2- (3-hydroxyphenyl) propane, 2- (4- Aminophenyl) -2- (4-hydroxyphenyl) propane 1,4-bis (1- (4-aminophenyl)
  • Examples of the amide group-containing compound include Nt-butoxycarbonyl-4-hydroxypiperidine, Nt-butoxycarbonyl-2-carboxy-4-hydroxypyrrolidine, and Nt-butoxycarbonyl-2-carboxypyrrolidine.
  • Nt-butoxycarbonyl group-containing amino compounds Nt-amyloxycarbonyl group-containing amino compounds such as Nt-amyloxycarbonyl-4-hydroxypiperidine, N- (9-anthrylmethyloxycarbonyl) piperidine, etc.
  • N- (9-anthrylmethyloxycarbonyl) group-containing amino compounds formamide, N-methylformamide, N, N-dimethylformamide, acetamide, N-methylacetamide, N, N-dimethylacetamide, propionamide, benzamide, Piro Don, N- methylpyrrolidone, N- acetyl-1-adamantyl amine, and the like.
  • urea compound examples include urea, methylurea, 1,1-dimethylurea, 1,3-dimethylurea, 1,1,3,3-tetramethylurea, 1,3-diphenylurea, tri-n-butylthiourea. Etc.
  • nitrogen-containing heterocyclic compound examples include imidazoles, pyridines, piperazines, pyrazines, pyrazoles, pyridazines, quinosalines, purines, pyrrolidines, piperidines, piperidine ethanol, 3- (N-piperidino) -1,2-propanediol. , Morpholine, 4-methylmorpholine, 1- (4-morpholinyl) ethanol, 4-acetylmorpholine, 3- (N-morpholino) -1,2-propanediol, 1,4-dimethylpiperazine, 1,4-diazabicyclo [ 2.2.2] octane and the like.
  • an amide group-containing compound and a nitrogen-containing heterocyclic compound are particularly preferable.
  • an Nt-butoxycarbonyl group-containing amino compound, an Nt-amyloxycarbonyl group-containing amino compound, and an N- (9-anthrylmethyloxycarbonyl) group-containing amino compound are more preferable.
  • Nt-butoxycarbonyl-4-hydroxypiperidine, Nt-butoxycarbonyl-2-carboxy-4-hydroxypyrrolidine, Nt-butoxycarbonyl-2-carboxy-pyrrolidine, Nt-amyloxycarbonyl-4 More preferred are -hydroxypiperidine and N- (9-anthrylmethyloxycarbonyl) piperidine.
  • the nitrogen-containing heterocyclic compound 3- (N-piperidino) -1,2-propanediol is preferable.
  • the content of the basic compound with respect to 100 parts by mass of [A] polysiloxane is preferably 0.01 parts by mass, and 0.1% by mass. More preferably, 0.5 part by mass is further preferable, and 1 part by mass is particularly preferable. As an upper limit of the said content, 20 mass parts is preferable, 10 mass parts is more preferable, and 5 mass parts is further more preferable.
  • the acid generator is a compound that generates an acid upon irradiation with ultraviolet light and / or heating.
  • the silicon-containing film-forming composition contains an acid generator, curing can be promoted, and as a result, the strength of the silicon-containing film can be further increased, and solvent resistance and oxygen gas etching resistance can be increased. it can.
  • An acid generator can be used individually by 1 type or in combination of 2 or more types.
  • Examples of the acid generator include onium salt compounds and N-sulfonyloxyimide compounds.
  • onium salt compounds examples include sulfonium salts, tetrahydrothiophenium salts, iodonium salts, ammonium salts, and the like.
  • Examples of the sulfonium salt include the sulfonium salts described in paragraph [0110] of JP-A-2014-037386, and more specifically, triphenylsulfonium trifluoromethanesulfonate, triphenylsulfonium nonafluoro-n-butanesulfonate, Examples include triphenylsulfonium 2-bicyclo [2.2.1] hept-2-yl-1,1,2,2-tetrafluoroethane sulfonate, 4-cyclohexylphenyl diphenylsulfonium trifluoromethane sulfonate, and the like.
  • tetrahydrothiophenium salt examples include tetrahydrothiophenium salts described in paragraph [0111] of JP 2014-037386 A, and more specifically, 1- (4-n-butoxynaphthalene-1- Yl) tetrahydrothiophenium trifluoromethanesulfonate, 1- (4-n-butoxynaphthalen-1-yl) tetrahydrothiophenium nonafluoro-n-butanesulfonate, 1- (4-n-butoxynaphthalen-1-yl) And tetrahydrothiophenium 2-bicyclo [2.2.1] hept-2-yl-1,1,2,2-tetrafluoroethanesulfonate.
  • iodonium salts examples include iodonium salts described in paragraph [0112] of JP 2014-037386 A, and more specifically, diphenyliodonium trifluoromethanesulfonate, diphenyliodonium nonafluoro-n-butanesulfonate, diphenyliodonium.
  • examples include 2-bicyclo [2.2.1] hept-2-yl-1,1,2,2-tetrafluoroethane sulfonate, bis (4-t-butylphenyl) iodonium nonafluoro-n-butane sulfonate, and the like. .
  • ammonium salt examples include trimethylammonium nonafluoro-n-butanesulfonate, triethylammonium nonafluoro-n-butanesulfonate, and the like.
  • N-sulfonyloxyimide compound examples include N-sulfonyloxyimide compounds described in paragraph [0113] of JP-A No. 2014-037386, and more specifically, 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-di Carboximide, N- (2-bicyclo [2.2.1] hept-2-yl-1,1,2,2-tetrafluoroethanesulfonyloxy) bicyclo [2.2.1] hept-5-ene- 2,3-dicarboximide and the like can be mentioned.
  • the content of the acid generator with respect to 100 parts by mass of [A] polysiloxane is preferably 0.01 parts by mass, and 0.1% by mass. More preferably, 0.5 part by mass is further preferable, and 1 part by mass is particularly preferable. As an upper limit of the said content, 20 mass parts is preferable, 10 mass parts is more preferable, and 5 mass parts is further more preferable.
  • the silicon-containing film-forming composition may contain other optional components in addition to the basic compound and the acid generator.
  • other optional components include surfactants, radical generators, colloidal silica, colloidal alumina, and organic polymers.
  • the upper limit of the content is preferably 2 parts by mass and more preferably 1 part by mass with respect to 100 parts by mass of [A] polysiloxane. .
  • the method for preparing the composition for forming a silicon-containing film is not particularly limited, and for example, [A] polysiloxane, [B] solvent and optional components are mixed at a predetermined ratio, preferably, the obtained mixture
  • the solution can be prepared by filtering with a filter having a pore size of 0.2 ⁇ m.
  • the lower limit of the solid content concentration of the silicon-containing film forming composition is preferably 0.01% by mass, more preferably 0.05% by mass, still more preferably 0.1% by mass, and particularly preferably 0.2% by mass. preferable.
  • the upper limit of the solid content concentration is preferably 20% by mass, more preferably 10% by mass, further preferably 5% by mass, and particularly preferably 3% by mass.
  • the solid content concentration of the silicon-containing film-forming composition means that the mass of the solid content in the silicon-containing film-forming composition is measured by baking the silicon-containing film-forming composition at 250 ° C. for 30 minutes, It is a value (mass%) calculated by dividing the mass of this solid content by the mass of the composition for forming a silicon-containing film.
  • the silicon-containing film-forming composition can be suitably used as a film-forming material in a resist process such as a silicon-containing film as an intermediate film in a multilayer resist process, and a pattern (inverted pattern) obtained through an inversion process It can also be used for applications other than the film forming material in the resist process, such as the forming material.
  • the silicon-containing film obtained from the silicon-containing film-forming composition is excellent in resist pattern collapse suppression while maintaining etching removability with a fluorine-based gas, and is resistant to an alkaline developer in the resist pattern forming step. Excellent resistance and exfoliation with alkaline hydrogen peroxide. Therefore, the composition for forming a silicon-containing film can be suitably used as a material for forming a silicon-containing film as an intermediate film in a resist process, particularly a multilayer resist process.
  • the multilayer resist processes it is particularly preferably used in pattern formation using a multilayer resist process in a region finer than 90 nm (ArF, ArF in immersion exposure, F 2 , EUV, nanoimprint, etc.). it can.
  • the silicon-containing film forms a coating film by applying the above-mentioned composition for forming a silicon-containing film to the surface of another lower layer film such as a substrate or an organic lower layer film, and heat-treats the coating film. Then, it can be formed by curing.
  • Examples of the method for applying the silicon-containing film forming composition include a spin coating method, a roll coating method, and a dip method.
  • a spin coating method As a minimum of the temperature of heat processing, 50 ° C is preferred and 70 ° C is more preferred.
  • As an upper limit of the said temperature 450 degreeC is preferable and 300 degreeC is more preferable.
  • the lower limit of the average thickness of the formed silicon-containing film is preferably 10 nm, more preferably 20 nm.
  • the upper limit of the average thickness is preferably 200 nm, and more preferably 150 nm.
  • the pattern forming method includes a step of forming a silicon-containing film on the upper side of a substrate by applying the silicon-containing film-forming composition (hereinafter also referred to as “silicon-containing film forming step”), and patterning the silicon-containing film. (Hereinafter, also referred to as “silicon-containing film patterning step”).
  • the silicon-containing film-forming composition described above since the silicon-containing film-forming composition described above is used, it is possible to form a silicon-containing film that is excellent in resist pattern collapse suppression while maintaining etching removability with a fluorine-based gas. In addition, it is possible to form a silicon-containing film that is excellent in resistance to an alkaline developer in the resist pattern forming step and excellent in releasability with alkaline hydrogen peroxide.
  • the silicon-containing film patterning step includes a step of forming a resist pattern on the upper side of the silicon-containing film (hereinafter also referred to as “resist pattern forming step”), and a step of etching the silicon-containing film using the resist pattern as a mask. (Hereinafter also referred to as “silicon-containing film etching step”).
  • the pattern forming method may further include a step of forming an organic underlayer film on the upper side of the substrate (hereinafter, also referred to as “organic underlayer film forming step”) before the silicon-containing film forming step, if necessary. Good.
  • the pattern forming method may further include a step of removing the silicon-containing film (hereinafter, also referred to as “silicon-containing film removing step”) after the silicon-containing film forming step.
  • the pattern forming method usually includes a step of etching a substrate (hereinafter also referred to as “substrate etching step”) using the patterned silicon-containing film as a mask after the silicon-containing film patterning step.
  • substrate etching step etching a substrate
  • Organic underlayer formation process In this step, an organic underlayer film is formed on the upper side of the substrate.
  • an organic underlayer film forming step can be performed as necessary.
  • the silicon-containing film forming step is performed after the organic underlayer film forming step, and the silicon-containing film forming composition is formed on the organic underlayer film in the silicon-containing film forming step. Is used to form a silicon-containing film.
  • the substrate examples include an insulating film such as silicon oxide, silicon nitride, silicon oxynitride, and polysiloxane, a resin substrate, and the like.
  • an interlayer insulating film such as a wafer covered with a low dielectric insulating film formed by “Black Diamond” from AMAT, “Silk” from Dow Chemical, “LKD5109” from JSR, or the like can be used.
  • a patterned substrate such as a wiring groove (trench) or a plug groove (via) may be used.
  • the organic underlayer film is different from the silicon-containing film formed from the silicon-containing film forming composition.
  • the organic underlayer film has a predetermined function (for example, antireflection) that is necessary for further supplementing the function of the silicon-containing film and / or the resist film in the formation of the resist pattern, or to obtain a function that these do not have. Film, coating film flatness, and high etching resistance against fluorine-based gas).
  • Examples of the organic underlayer film include an antireflection film.
  • Examples of the composition for forming an antireflection film include “NFC HM8006” manufactured by JSR Corporation.
  • the organic underlayer film can be formed by applying a composition for forming an organic underlayer film by a spin coating method or the like to form a coating film, followed by heating.
  • a silicon-containing film is formed on the upper side of the substrate by applying the silicon-containing film-forming composition.
  • a silicon-containing film is formed on the substrate directly or via another layer such as an organic underlayer film.
  • the method for forming the silicon-containing film is not particularly limited.
  • the coating film formed by applying the silicon-containing film-forming composition onto a substrate or the like by a known method such as a spin coating method may be exposed and / or Examples of the method include a method of curing by heating.
  • Examples of the radiation used for this exposure include electromagnetic waves such as visible light, ultraviolet rays, far ultraviolet rays, X-rays and ⁇ rays, particle beams such as electron beams, molecular beams and ion beams.
  • the temperature at the time of heating a coating film 90 ° C is preferred, 150 ° C is more preferred, and 200 ° C is still more preferred.
  • As an upper limit of the said temperature 550 degreeC is preferable, 450 degreeC is more preferable, and 300 degreeC is further more preferable.
  • As a minimum of average thickness of a silicon content film formed 1 nm is preferred, 10 nm is more preferred, and 20 nm is still more preferred.
  • the upper limit of the average thickness is preferably 20,000 nm, more preferably 1,000 nm, and even more preferably 100 nm.
  • ⁇ Silicon-containing film patterning process> the silicon-containing film is patterned.
  • the silicon-containing film formed in the silicon-containing film forming step is patterned.
  • Examples of the method for patterning the silicon-containing film include a method including a resist pattern forming step and a silicon-containing film etching step.
  • resist pattern formation process In this step, a resist pattern is formed on the upper side of the silicon-containing film. By this step, a resist pattern is formed on the upper side of the silicon-containing film formed in the silicon-containing film forming step.
  • Examples of the method for forming a resist pattern include conventionally known methods such as a method using a resist composition and a method using a nanoimprint lithography method. This resist pattern is usually formed from an organic material.
  • a step of forming a resist film on the upper side of the silicon-containing film with the resist composition for example, a step of forming a resist film on the upper side of the silicon-containing film with the resist composition (hereinafter also referred to as “resist film forming step”), and a step of exposing the resist film (hereinafter also referred to as “development step”) may be used.
  • resist film formation process In this step, a resist film is formed on the upper side of the silicon-containing film with a resist composition. By this step, a resist film is formed on the upper side of the silicon-containing film.
  • the resist composition examples include a radiation-sensitive resin composition (chemically amplified resist composition) containing a polymer having an acid-dissociable group and a radiation-sensitive acid generator, an alkali-soluble resin, and a quinonediazide-based photosensitizer. And a negative resist composition containing an alkali-soluble resin and a crosslinking agent.
  • a radiation sensitive resin composition is preferable.
  • a positive pattern can be formed by developing with an alkali developer
  • a negative pattern can be formed by developing with an organic solvent developer.
  • a double patterning method, a double exposure method, or the like, which is a method for forming a fine pattern may be used as appropriate.
  • the polymer contained in the radiation-sensitive resin composition includes, in addition to the structural unit containing an acid dissociable group, for example, a structural unit containing a lactone structure, a cyclic carbonate structure and / or a sultone structure, or a structural unit containing an alcoholic hydroxyl group. Further, it may have a structural unit containing a phenolic hydroxyl group, a structural unit containing a fluorine atom, or the like.
  • EUV extreme ultraviolet rays
  • the lower limit of the solid content concentration of the resist composition is preferably 0.1% by mass, and more preferably 1% by mass.
  • As an upper limit of the said solid content concentration 50 mass% is preferable and 30 mass% is more preferable.
  • As the resist composition a resist composition filtered with a filter having a pore diameter of about 0.2 ⁇ m can be suitably used. In the pattern forming method, a commercially available resist composition can be used as it is as the resist composition.
  • Examples of the resist film forming method include a method of coating a resist composition on a silicon-containing film.
  • Examples of the resist composition coating method include conventional methods such as a spin coating method. When applying the resist composition, the amount of the resist composition to be applied is adjusted so that the resulting resist film has a predetermined thickness.
  • the resist film can be formed by volatilizing the solvent in the coating film by pre-baking the coating film of the resist composition.
  • the pre-baking temperature is appropriately adjusted according to the type of resist composition to be used, and the like.
  • the lower limit of the pre-baking temperature is preferably 30 ° C., more preferably 50 ° C.
  • 200 degreeC is preferable and 150 degreeC is more preferable.
  • the resist film is exposed. This exposure is performed by selectively irradiating radiation, for example, through a photomask.
  • the radiation used for the exposure includes electromagnetic waves such as visible rays, ultraviolet rays, far ultraviolet rays, X-rays, ⁇ rays, electron beams, molecular rays, ions, depending on the type of acid generator used in the resist composition.
  • electromagnetic waves such as visible rays, ultraviolet rays, far ultraviolet rays, X-rays, ⁇ rays, electron beams, molecular rays, ions, depending on the type of acid generator used in the resist composition.
  • a particle beam such as a beam is appropriately selected, and among these, deep ultraviolet rays and electron beams are preferable, and KrF excimer laser light (248 nm), ArF excimer laser light (193 nm), F 2 excimer laser light (wavelength 157 nm).
  • the exposure method is not particularly limited, and can be performed in accordance with a conventionally known pattern formation method.
  • the development may be alkali development or organic solvent development.
  • alkali developer examples include sodium hydroxide, potassium hydroxide, sodium carbonate, sodium silicate, sodium metasilicate, ammonia, ethylamine, n-propylamine, diethylamine, di-n-propylamine, triethylamine, methyldiethylamine, dimethylethanol.
  • alkaline aqueous solutions in which at least one of the alkaline compounds is dissolved.
  • these alkaline aqueous solutions may be those obtained by adding appropriate amounts of water-soluble organic solvents such as alcohols such as methanol and ethanol, surfactants and the like.
  • organic solvent developer examples include liquids mainly composed of organic solvents such as ketone solvents, alcohol solvents, amide solvents, ether solvents, ester solvents and the like.
  • organic solvents such as ketone solvents, alcohol solvents, amide solvents, ether solvents, ester solvents and the like.
  • these solvents include those similar to the respective solvents exemplified as the above [B] solvent. These solvents may be used alone or in combination.
  • a predetermined resist pattern corresponding to the photomask can be formed by washing and drying.
  • the silicon-containing film is etched using the resist pattern as a mask. More specifically, a silicon-containing film on which a pattern is formed is obtained by one or more etchings using the resist pattern formed in the resist pattern forming step as a mask.
  • the etching may be dry etching or wet etching, but is preferably dry etching.
  • Dry etching can be performed using, for example, a known dry etching apparatus.
  • the etching gas used for dry etching can be selected as appropriate depending on the elemental composition of the silicon-containing film to be etched, such as CHF 3 , CF 4 , C 2 F 6 , C 3 F 8 , SF 6, etc.
  • Fluorine gas chlorine gas such as Cl 2 , BCl 3 , oxygen gas such as O 2 , O 3 , H 2 O, H 2 , NH 3 , CO, CO 2 , CH 4 , C 2 H 2 , C 2 H 4 , C 2 H 6 , C 3 H 4 , C 3 H 6 , C 3 H 8 , HF, HI, HBr, HCl, NO, NH 3 , reducing gases such as BCl 3 , He, N 2 , An inert gas such as Ar is used. These gases can also be mixed and used. For dry etching of a silicon-containing film, a fluorine-based gas is usually used, and a mixture of an oxygen-based gas and an inert gas is preferably used.
  • the substrate is etched using the patterned silicon-containing film as a mask. More specifically, the patterned substrate is obtained by performing etching one or more times using the pattern formed on the silicon-containing film obtained in the silicon-containing film etching step as a mask.
  • the organic underlayer film is formed by etching the organic underlayer film using the silicon-containing film pattern as a mask, and then the substrate is etched using the organic underlayer film pattern as a mask. Thus, a pattern is formed on the substrate.
  • the etching may be dry etching or wet etching, but is preferably dry etching.
  • Dry etching for forming a pattern on the organic underlayer film can be performed using a known dry etching apparatus.
  • the etching gas used for the dry etching can be appropriately selected depending on the elemental composition of the gas silicon-containing film and the organic underlayer film to be etched.
  • An inert gas such as He, N 2 , or Ar is used, and these gases may be used in combination.
  • an oxygen-based gas is usually used for dry etching of an organic underlayer film using a silicon-containing film pattern as a mask.
  • Dry etching for forming a pattern on a substrate using an organic underlayer film pattern as a mask can be performed using a known dry etching apparatus.
  • the etching gas used for the dry etching can be appropriately selected depending on the elemental composition of the organic underlayer film and the substrate to be etched, and is similar to those exemplified as the etching gas used for the dry etching of the organic underlayer film.
  • the silicon-containing film is removed after the silicon-containing film forming step.
  • this step is performed after the substrate etching step, the silicon-containing film remaining on the upper side of the substrate is removed.
  • This step can also be performed on a patterned or non-patterned silicon-containing film before the substrate etching step. That is, for example, when a defect occurs in the formation of a silicon-containing film, or when a defect occurs in the patterned silicon-containing film before the substrate etching process, this step is performed without discarding the substrate. It is possible to start again from the silicon-containing film forming step.
  • Examples of the method for removing the silicon-containing film include a method of dry etching the silicon-containing film, and a method of bringing a liquid such as a basic liquid or an acidic liquid into contact with the silicon-containing film.
  • a liquid such as a basic liquid or an acidic liquid.
  • a basic liquid is preferable.
  • the dry etching can be performed using a known dry etching apparatus. Further, as a source gas at the time of dry etching, for example, a fluorine gas such as CHF 3 , CF 4 , C 2 F 6 , C 3 F 8 , SF 6 , a chlorine gas such as Cl 2 , BCl 3, or the like is used. These gases can be mixed and used.
  • a fluorine gas such as CHF 3 , CF 4 , C 2 F 6 , C 3 F 8 , SF 6
  • a chlorine gas such as Cl 2 , BCl 3, or the like.
  • the wet stripping method is not particularly limited as long as the silicon-containing film and the alkaline hydrogen peroxide solution can be in contact with each other for a certain period of time under heating conditions, for example, a silicon-containing film.
  • substrate which has this in the heated alkaline hydrogen peroxide solution, the method of spraying alkaline hydrogen peroxide solution in a heating environment, the method of coating the heated alkaline hydrogen peroxide solution, etc. are mentioned. After each of these methods, the substrate may be washed with water and dried.
  • the lower limit of the temperature when the silicon-containing film removing step is performed using alkaline hydrogen peroxide is preferably 40 ° C., more preferably 50 ° C.
  • 90 degreeC is preferable and 80 degreeC is more preferable.
  • the lower limit of the dipping time in the dipping method is preferably 0.2 minutes, and more preferably 0.5 minutes.
  • the upper limit of the immersion time is preferably 30 minutes, more preferably 20 minutes, further preferably 10 minutes, and particularly preferably 5 minutes from the viewpoint of suppressing the influence on the substrate.
  • Example shown below shows an example of the typical Example of this invention, and, thereby, the range of this invention is not interpreted narrowly.
  • the measurement of the solid content concentration in the [A] polysiloxane solution and the measurement of the weight average molecular weight (Mw) of [A] polysiloxane in this example were performed by the following methods.
  • Average thickness of film The average thickness of the film was measured using a spectroscopic ellipsometer (“M2000D” from JA WOOLLAM).
  • the inside of the reaction vessel was cooled to 30 ° C. or lower.
  • the alcohol produced by the reaction and excess propylene glycol monoethyl ether were removed using an evaporator, and the propylene of polysiloxane (A-1) was removed.
  • a glycol monoethyl ether solution was obtained.
  • the Mw of the polysiloxane (A-1) was 1,800.
  • the solid content concentration of this polysiloxane (A-1) in propylene glycol monoethyl ether solution was 10.7% by mass.
  • composition for forming silicon-containing film ⁇ Preparation of composition for forming silicon-containing film> Components other than [A] polysiloxane used for the preparation of the silicon-containing film-forming composition are shown below.
  • B-1 Propylene glycol monomethyl ether acetate
  • B-2 Propylene glycol monoethyl ether
  • Example 1 [A] 2.2 parts by mass of (A-1) as a polysiloxane (solid content), 10 parts by mass of (B-1) and (B-2) 90 parts by mass of (B) as a solvent ([A] And a solvent (B-2) contained in a polysiloxane solution), and the resulting solution is filtered through a filter having a pore size of 0.2 ⁇ m to obtain a silicon-containing film-forming composition (J-1).
  • A 2.2 parts by mass of (A-1) as a polysiloxane (solid content), 10 parts by mass of (B-1) and (B-2) 90 parts by mass of (B) as a solvent ([A] And a solvent (B-2) contained in a polysiloxane solution), and the resulting solution is filtered through a filter having a pore size of 0.2 ⁇ m to obtain a silicon-containing film-forming composition (J-1).
  • Example 2 to 20 and Comparative Examples 1 and 2 The silicon-containing film-forming compositions (J-2) to (J-20) and (j-1) were obtained in the same manner as in Example 1 except that the components of the types and blending amounts shown in Table 2 were used. And (j-2) were prepared.
  • Each of the silicon-containing film-forming compositions prepared above was coated on a silicon wafer (substrate) by a spin coating method using a spin coater (“CLEAN TRACK ACT12” manufactured by Tokyo Electron Ltd.).
  • the obtained coating film was heated on a hot plate at 220 ° C. for 60 seconds, and then cooled at 23 ° C. for 60 seconds, whereby the average thickness of 35 nm shown in Examples 1 to 20 and Comparative Examples 1 and 2 in Table 2 was obtained.
  • a substrate on which a silicon-containing film was formed was obtained.
  • the substrate on which the silicon-containing film was formed was immersed in an aqueous 2.38 mass% tetramethylammonium hydroxide (TMAH) solution (20 to 25 ° C.) for 60 seconds and washed with water.
  • TMAH tetramethylammonium hydroxide
  • Film thickness change rate (%)
  • the resistance to alkaline developer was evaluated as “A” (good) when the film thickness change rate was less than 1%, and “B” (bad) when the film thickness change rate was 1% or more.
  • SC1 mixed liquid
  • the average thickness of the film before and after immersion was measured.
  • the film thickness change rate (%) due to SC1 immersion was determined by the following formula.
  • Film thickness change rate (%) (S 0 ⁇ S 1 ) ⁇ 100 / S 0
  • the peelability by the alkaline hydrogen peroxide solution was evaluated as “A” (good) when the rate of change in film thickness was 99% or more, and “B” (bad) when it was less than 99%.
  • a radiation sensitive resin composition (“ARF AR2772JN” manufactured by JSR) is coated on the silicon-containing film by the spin coater, heat-treated at 90 ° C. for 60 seconds, and then cooled at 23 ° C. for 30 seconds. Thus, a resist film having an average thickness of 100 nm was formed.
  • ArF immersion exposure apparatus (“S610C” manufactured by NIKON)
  • exposure was performed through a mask having a mask size for forming a 40 nm line / 80 nm pitch under the optical conditions of NA: 1.30 and Dipole. Heat treatment is performed at 100 ° C. for 60 seconds on a “Lithius Pro-i” hot plate, cooled at 23 ° C.
  • the collapse inhibition property (1) is “A” (good) when the minimum pre-collapse dimension is 32 nm or less, “B” (slightly good) when it exceeds 32 nm and 38 nm or less, and “C” when it exceeds 38 nm. "(Poor).
  • the substrate for evaluation on which a resist pattern was formed was obtained by washing with water and drying.
  • the exposure amount formed in a one-to-one line and space with a line width of 150 nm was determined as the optimum exposure amount.
  • a scanning electron microscope (“CG-4000” manufactured by Hitachi High-Technologies Corporation) was used for measuring and observing the resist pattern on the evaluation substrate.
  • the collapse inhibition property (2) was evaluated as “A” (good) when pattern collapse was not confirmed and “B” (bad) when pattern collapse was confirmed at the optimum exposure amount.
  • the etching removability by the fluorine-based gas is “A” (good) when the etching rate is 60 (nm / min) or more, and “B” when the etching rate is 55 (nm / min) or more and less than 60 (nm / min). (Slightly good) and less than 55 (nm / min) were evaluated as “C” (bad).
  • the silicon-containing film forming compositions of the examples are excellent in storage stability, excellent in resistance to an alkaline developer, and excellent in peelability with alkaline hydrogen peroxide, and etched with a fluorine-based gas. It is possible to form a silicon-containing film that is excellent in removability and excellent in resist pattern collapse suppression. In general, it is known that electron beam exposure shows the same tendency as in EUV exposure. Therefore, according to the composition for forming a silicon-containing film of Examples, even in the case of EUV exposure. It is presumed that the resist pattern collapse resistance is excellent.
  • the composition for forming a silicon-containing film and the pattern forming method of the present invention it is possible to form a silicon-containing film that is excellent in resist pattern collapse suppression while maintaining the etching removability with a fluorine-based gas. It is possible to form a silicon-containing film that is excellent in resistance to an alkaline developer in the resist pattern forming step and excellent in releasability with alkaline hydrogen peroxide. Furthermore, the silicon-containing film forming composition of the present invention is excellent in storage stability. The silicon-containing film of the present invention is excellent in resistance to an alkali developer while maintaining etching removability by a fluorine-based gas and excellent in peelability by an alkaline hydrogen peroxide solution.
  • the polysiloxane of the present invention can be suitably used as a polysiloxane component of the silicon-containing film forming composition. Therefore, these can be used suitably for a multilayer resist process, and can be used suitably for manufacture of a semiconductor device etc. which are expected to be further miniaturized in the future.

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Abstract

La présente invention a pour objet de réaliser : une composition pour la formation de film contenant du silicium capable de former un film contenant du silicium qui conserve l'aptitude à l'enlèvement par gravure avec un gaz à base de fluor et qui est excellent en termes d'inhibition de la chute des parois de motif de réserve ; le film contenant du silicium ; un procédé de formation de motif ; et un polysiloxane. La composition pour la formation de film contenant du silicium comprend un polysiloxane ayant un groupe représenté par la formule (1) et un solvant. Dans la formule (1), L est une liaison simple ou un groupe organique en C1-20 (n+1)-valent, E est un groupe représenté par la formule (2-1) ou (2-2), Y1 est un groupe aryle (non) substitué en C6-20 ou un groupe hydrocarboné aliphatique monovalent en C1-20 dans lequel un atome d'hydrogène a été remplacé par un groupe attirant les électrons, et Y2 est un groupe arylénediyle (non) substitué en C6-20 ou un groupe hydrocarboné aliphatique divalent en C1-20 dans lequel un atome d'hydrogène a été remplacé par un groupe attirant les électrons.
PCT/JP2018/005724 2017-03-02 2018-02-19 Composition pour formation de film contenant du silicium, film contenant du silicium, procédé de formation de motif et polysiloxane Ceased WO2018159356A1 (fr)

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JPWO2022149478A1 (fr) * 2021-01-07 2022-07-14

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Publication number Priority date Publication date Assignee Title
JP7357505B2 (ja) 2018-11-21 2023-10-06 信越化学工業株式会社 ヨウ素含有熱硬化性ケイ素含有材料、これを含むｅｕｖリソグラフィー用レジスト下層膜形成用組成物、及びパターン形成方法
JP7368324B2 (ja) 2019-07-23 2023-10-24 信越化学工業株式会社 ケイ素含有レジスト下層膜形成用組成物及びパターン形成方法

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JPH03206461A (ja) * 1990-01-09 1991-09-09 Fuji Photo Film Co Ltd 感光性組成物
JPH05262812A (ja) * 1991-11-14 1993-10-12 Dow Corning Ltd 輻射線硬化性組成物
JP2000336093A (ja) * 1999-05-26 2000-12-05 Jsr Corp 加水分解性シラン化合物およびその製造方法
JP2010085878A (ja) * 2008-10-02 2010-04-15 Tokyo Ohka Kogyo Co Ltd レジスト下層膜形成用組成物
JP2011515514A (ja) * 2008-03-04 2011-05-19 ダウ・コーニング・コーポレイション シルセスキオキサン樹脂
WO2012114864A1 (fr) * 2011-02-24 2012-08-30 日産化学工業株式会社 Composé silane et composition pour la formation d'une monocouche ou d'une multicouche à l'aide de celui-ci
WO2014098076A1 (fr) * 2012-12-19 2014-06-26 日産化学工業株式会社 Composition pour former un film de sous-couche résistant contenant du silicium et comprenant un groupe de diester cyclique
WO2016111210A1 (fr) * 2015-01-09 2016-07-14 Jsr株式会社 Composition pour former un film contenant du silicium et procédé de formation de motif utilisant ladite composition
JP2016130809A (ja) * 2015-01-14 2016-07-21 Jsr株式会社 硬化膜形成用感放射線性組成物、硬化膜、表示素子及び硬化膜の形成方法

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Publication number Priority date Publication date Assignee Title
JPH03206461A (ja) * 1990-01-09 1991-09-09 Fuji Photo Film Co Ltd 感光性組成物
JPH05262812A (ja) * 1991-11-14 1993-10-12 Dow Corning Ltd 輻射線硬化性組成物
JP2000336093A (ja) * 1999-05-26 2000-12-05 Jsr Corp 加水分解性シラン化合物およびその製造方法
JP2011515514A (ja) * 2008-03-04 2011-05-19 ダウ・コーニング・コーポレイション シルセスキオキサン樹脂
JP2010085878A (ja) * 2008-10-02 2010-04-15 Tokyo Ohka Kogyo Co Ltd レジスト下層膜形成用組成物
WO2012114864A1 (fr) * 2011-02-24 2012-08-30 日産化学工業株式会社 Composé silane et composition pour la formation d'une monocouche ou d'une multicouche à l'aide de celui-ci
WO2014098076A1 (fr) * 2012-12-19 2014-06-26 日産化学工業株式会社 Composition pour former un film de sous-couche résistant contenant du silicium et comprenant un groupe de diester cyclique
WO2016111210A1 (fr) * 2015-01-09 2016-07-14 Jsr株式会社 Composition pour former un film contenant du silicium et procédé de formation de motif utilisant ladite composition
JP2016130809A (ja) * 2015-01-14 2016-07-21 Jsr株式会社 硬化膜形成用感放射線性組成物、硬化膜、表示素子及び硬化膜の形成方法

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPWO2022149478A1 (fr) * 2021-01-07 2022-07-14
JP7661367B2 (ja) 2021-01-07 2025-04-14 Jsr株式会社 組成物及び半導体基板の製造方法

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