WO2006064622A1 - Composition de resistpositif et procede de formation d’un motif de resist - Google Patents

Composition de resistpositif et procede de formation d’un motif de resist Download PDF

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Publication number
WO2006064622A1
WO2006064622A1 PCT/JP2005/020419 JP2005020419W WO2006064622A1 WO 2006064622 A1 WO2006064622 A1 WO 2006064622A1 JP 2005020419 W JP2005020419 W JP 2005020419W WO 2006064622 A1 WO2006064622 A1 WO 2006064622A1
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Prior art keywords
group
component
alkyl group
acid
resist composition
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PCT/JP2005/020419
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English (en)
Japanese (ja)
Inventor
Yusuke Nakagawa
Shinichi Hidesaka
Kazuhiko Nakayama
Ryotaro Hayashi
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Tokyo Ohka Kogyo Co., Ltd.
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Publication of WO2006064622A1 publication Critical patent/WO2006064622A1/fr

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors

Definitions

  • the present invention relates to a positive resist composition and a resist pattern forming method.
  • Such a resist for a short wavelength light source is required to have high resolution capable of reproducing a pattern with a fine dimension and high sensitivity to such a short wavelength light source.
  • a chemically amplified resist containing a base resin and an acid generator (PAG) that generates acid upon exposure is known.
  • PAG acid generator
  • Patent Document 1 Japanese Patent Laid-Open No. 2003-167347
  • the present invention has been made in view of the above circumstances, and an object thereof is to provide a positive resist composition and a resist pattern forming method capable of improving the EL margin and dimensional fidelity. .
  • the positive resist composition of the present invention comprises a resin component (A) whose alkali solubility is increased by the action of an acid, and an acid generator component (B which generates an acid upon exposure).
  • the component (B) is an onion salt acid generator (B1) having a cation moiety represented by the following general formula (b-1), and the following general formula: It is characterized by containing an oxime sulfonate acid generator (B2) having a structure represented by (b-2).
  • R 1 ′′ represents an alkyl group, an alkoxy group, a halogen atom, or a hydroxyl group
  • R ′′ ′ and R 3 ′′ each independently represent an aryl group or alkyl which may have a substituent.
  • R 1 represents an organic group, and represents a monovalent organic group or a cyano group.
  • the present invention also includes a step of forming a resist film on a substrate using the positive resist composition of the present invention, a step of exposing the resist film, and a step of developing the resist film to form a resist pattern.
  • a resist pattern forming method is provided.
  • a resist type resist composition and a method for forming a resist pattern that can improve the EL margin and dimensional fidelity of the resist pattern.
  • the component (A) is an alkali-insoluble resin having a so-called acid dissociable dissolution inhibiting group.
  • an acid is generated from the component (B) by exposure, the force and the acid release the acid dissociable dissolution inhibiting group. As a result, the component (A) becomes alkali-soluble.
  • the alkali solubility of the exposed portion increases and alkali development can be performed.
  • the component (A) is not particularly limited, and a resin that has been proposed as a base resin for a chemically amplified positive resist composition can be used.
  • the component (A) preferably has a structural unit (al) derived from an acrylate ester force having an acid dissociable, dissolution inhibiting group.
  • the “structural unit” represents a monomer unit constituting a polymer (resin).
  • “Acrylic acid-derived structural unit” means a structural unit formed by cleavage of an ethylenic double bond of acrylic acid.
  • the “structural unit derived from acrylate power” means a structural unit formed by cleavage of an ethylenic double bond of an acrylate ester.
  • ⁇ -position carbon atom at the position
  • the “structural unit derived from acrylic acid” is a structural unit in which a hydrogen atom bonded to a carbon atom at the ⁇ -position is substituted with another substituent such as a halogen atom, an alkyl group, or a halogenated alkyl group,
  • the concept includes a structural unit derived from an acrylic ester obtained by bonding a hydrogen atom to a carbon atom at the lower position.
  • alkyl group includes a linear, cyclic or branched aralkyl group unless otherwise specified.
  • the acid dissociable, dissolution inhibiting group in the structural unit (al) has an alkali dissolution inhibiting property that makes the entire resin component (A) insoluble before dissociation, and after dissociation, the entire resin component (A) As long as it can be changed to alkali-soluble, those that have been proposed as acid dissociable, dissolution inhibiting groups of base resins for chemically amplified resists can be used.
  • a carboxy group of (meth) acrylic acid and a group that forms a cyclic or chain tertiary alkyl ester or a group that forms a cyclic or chain alkoxyalkyl ester are widely known. Yes. More preferably, it is a group that forms a cyclic or chain tertiary alkyl ester with the carboxy group of (meth) acrylic acid.
  • (Meth) acrylic acid ester means one or both of acrylic acid ester and methacrylic acid ester.
  • the tertiary alkyl ester is an ester formed by substitution with a hydrogen atom of a carboxy group, an alkyl group or a cycloalkyl group, and the carbonyloxy group (_C ( ⁇ ) _o A structure in which the tertiary carbon atom of the alkyl group or cycloalkyl group is bonded to the oxygen atom at the terminal of-).
  • the bond is cut between the oxygen atom and the tertiary carbon atom.
  • the alkyl group or cycloalkyl group has a substituent. Moyore.
  • a group that becomes acid dissociable by constituting a carboxy group and a tertiary alkyl ester will be referred to as a “tertiary alkyl ester type acid dissociable, dissolution inhibiting group” for convenience.
  • a cyclic or chain alkoxyalkyl ester forms an ester by replacing the hydrogen atom of a carboxy group with an alkoxyalkyl group, and its force nonyloxy group (_C (O) -0-)
  • _C (O) -0 A structure in which the alkoxyalkyl group S is bonded to the oxygen atom at the terminal of In this alkoxyalkyl ester, when an acid acts, the bond is broken between the oxygen atom and the alkoxyalkyl group.
  • the structural unit (al) is selected from the group consisting of structural units represented by the following general formula (al_0_l) and structural units represented by the following general formula (al-0-2).
  • R represents a hydrogen atom, a fluorine atom, a lower alkyl group, or a fluorinated lower alkyl group
  • X 1 represents an acid dissociable, dissolution inhibiting group.
  • R is as defined above; X 2 represents an acid dissociable, dissolution inhibiting group; Y 2 represents an aliphatic cyclic group; Indicates. )
  • the lower alkyl group as R is an alkyl group having from 5 to 5 carbon atoms, and specifically includes a methylol group, an ethyl group, a propyl group, isopropyl And a lower linear or branched alkyl group such as n-butyl group, isobutyl group, tert_butyl group, pentyl group, isopentyl group, and neopentyl group.
  • the fluorinated lower alkyl group as R is an alkyl group having 1 to 5 carbon atoms, in which part or all of the hydrogen atoms of the alkyl group are substituted with fluorine atoms, and may be less than Are preferably fluorinated.
  • the fluorinated lower alkyl group having 1 to 5 carbon atoms is preferably a trifluoromethyl group such as a trifluoromethyl group, a hexafluoroethyl group, a heptafluoropropyl group, or a nonafluorobutyl group. More preferred.
  • X 1 is not particularly limited as long as it is an acid dissociable, dissolution inhibiting group, and examples thereof include an alkoxyalkyl group, a tertiary alkyl ester type acid dissociable, dissolution inhibiting group, and the like. Acid dissociable, dissolution inhibiting groups are preferred. Examples of the tertiary alkyl ester type acid dissociable, dissolution inhibiting group include aliphatic branched acid dissociable, dissolution inhibiting groups, and acid dissociable, dissolution inhibiting groups containing an aliphatic cyclic group.
  • aliphatic in the claims and the specification is a relative concept with respect to aromatics, and is defined to mean groups, compounds, and the like that do not have aromaticity.
  • the “aliphatic cyclic group” represents a monocyclic group or polycyclic group having no aromaticity.
  • the basic ring structure excluding the substituents of the “aliphatic cyclic group” is not limited to a group consisting of carbon and hydrogen (hydrocarbon group), but is a hydrocarbon group I prefer it. Further, the “hydrocarbon group” may be either saturated or unsaturated, but is usually preferably saturated. A polycyclic group is preferred.
  • aliphatic cyclic groups include, for example, lower alkyl groups, fluorine atoms Or one or more polycycloalkanes substituted with a fluorinated alkyl group, such as substituted, fluorinated, fluorinated alkyl groups, monocycloalkane, bicycloalkane, tricycloalkane, tetracycloalkane, etc.
  • fluorinated alkyl groups such as substituted, fluorinated, fluorinated alkyl groups, monocycloalkane, bicycloalkane, tricycloalkane, tetracycloalkane, etc.
  • Examples include a group excluding a hydrogen atom.
  • monocycloalkanes such as cyclopentane and cyclohexane
  • groups obtained by removing one or more hydrogen atoms from polycycloalkanes such as adamantane, norbornane, isobornane, tricyclodecane, and tetracyclododecane.
  • polycycloalkanes such as adamantane, norbornane, isobornane, tricyclodecane, and tetracyclododecane.
  • aliphatic branched acid dissociable, dissolution inhibiting group examples include a tert-butylol group and a tert-amyl group.
  • examples of the acid dissociable, dissolution inhibiting group containing an aliphatic cyclic group include a group having a tertiary carbon atom on the ring skeleton of the cycloalkyl group, specifically, 2-methyl.
  • examples include 2-adamantyl group and 2_ethyl_2-adamantyl group.
  • a group having an aliphatic cyclic group such as an adamantyl group and a branched alkylene group having a tertiary carbon atom bonded thereto is exemplified. It is done.
  • R is the same as described above, and R lb and R lb each represent an alkyl group (either linear or branched, preferably 1 to 5 carbon atoms). ]
  • the alkoxyalkyl group is preferably a group represented by the following general formula.
  • R 21 and R 22 are each independently an alkyl group or a hydrogen atom
  • R 23 is an alkyl group or a cycloalkyl group, or the ends of R 21 and R 23 are bonded to each other. To form a ring.
  • R 21, R 22, the carbon number of the alkyl group is preferably 1 to: a 15, linear, branched either Yogu Echiru group, is preferred instrument methyl group methyl group is most preferable.
  • one of R 21 and R 22 is preferably a hydrogen atom and the other is a katyl group.
  • R 23 is an alkyl group or a cycloalkyl group, and preferably has carbon number of:! To 15 and may be linear, branched or cyclic. In the case of straight chain or branched chain, R 23 preferably has 1 to 5 carbon atoms, more preferably a methyl group, and most preferably a ethyl group.
  • R 23 is cyclic, it is preferably 4 to 15 carbon atoms, more preferably 4 to 12 carbon atoms, and most preferably 5 to 10 carbon atoms.
  • R 23 is substituted with a fluorine atom or a fluorinated alkyl group, may or may not be, monocycloalkane, bicycloalkane, tricycloalkane. And groups obtained by removing one or more hydrogen atoms from a polycycloalkane such as tetracycloalkane.
  • monocycloalkanes such as cyclopentane and cyclohexane
  • groups obtained by removing one or more hydrogen atoms from polycycloalkanes such as adamantane, norbornane, isobornane, tricyclodecane, and tetracyclododecane. Is mentioned. Of these, groups in which one or more hydrogen atoms have been removed from adamantane are preferred.
  • R 21 and R 23 are each independently an alkylene group having 1 to 5 carbon atoms, and the end of R 23 and the end of R 21 may be bonded.
  • a cyclic group is formed by R 21 , R 23 , the oxygen atom to which R 23 is bonded, and the carbon atom to which the oxygen atom and R 21 are bonded.
  • a 4- to 7-membered ring is preferable, and a 4- to 6-membered ring is more preferable.
  • Specific examples of the cyclic group include a tetrahydropyrael group, a te And the like, and the like.
  • Y 2 is a divalent aliphatic cyclic group.
  • Y 2 is a divalent aliphatic cyclic group
  • aliphatic cyclic group in the description of the “aliphatic cyclic group” in the structural unit (al), a group in which two or more hydrogen atoms are removed is used. The same ones as described can be used.
  • X ′ represents a tertiary alkyl ester type acid dissociable, dissolution inhibiting group
  • Y represents a lower alkyl group of carbon number:! To 5 or an aliphatic cyclic group
  • n represents 0 or an integer of 1 to 3
  • m represents 0 or 1
  • R is the same as above
  • 1 ⁇ ′ and R 2 ′ are each independently a hydrogen atom or carbon number:! Represents a lower alkyl group.
  • At least one of R 1 'and R 2 ' is a hydrogen atom, more preferably both are water. It is an elementary atom. n is preferably 0 or 1.
  • X ' may be the same as the tertiary alkyl ester type acid dissociable, dissolution inhibiting group exemplified in X 1 above.
  • Examples of the aliphatic cyclic group for Y include the same groups as those exemplified in the description of the “aliphatic cyclic group” in the structural unit (al).
  • the structural unit (al) one type may be used alone, or two or more types may be used in combination.
  • the structural unit represented by the general formula (al_1) is preferred, and the structural unit represented by the general formula (al_l) or (al_3) is more preferable.
  • R represents a hydrogen atom or a lower alkyl group
  • R represents a lower alkyl group
  • h represents an integer of 1 to 3.
  • R is the same as described above.
  • the lower alkyl group for R ′′ is the same as the lower alkyl group represented by R, and is preferably a methyl group or an ethyl group.
  • R is the same as described above.
  • the lower alkyl group for R 12 is the same as the lower alkyl group represented by R, and is most preferably a methyl group or an ethyl group.
  • h is preferably 1 or 2, and most preferably 2.
  • the proportion of the structural unit (al) is the total structural unit constituting the resin component (A).
  • To 10 to 80 Monore 0/0 force S Preferably, preferably from 20 to 70 Monore 0/0 power S, more preferably 30 to 50 Monore 0/0 force S.
  • By setting it to the lower limit value or more a pattern can be obtained when the resist composition is used, and by setting the upper limit value or less, it is possible to balance with other structural units.
  • the resin component (A) preferably has, in addition to the structural unit (al), a structural unit (a2) derived from an acrylate ester having a latathone-containing monocyclic or polycyclic group.
  • the lathetone-containing monocyclic or polycyclic group of the structural unit (a2) can improve the adhesion of the resist film to the substrate or can be hydrophilic with the developer when the resin component (A) is used for forming a resist film. It is effective in enhancing the sex.
  • the ratatone-containing monocyclic or polycyclic group refers to a cyclic group containing one ring (lataton ring) containing a -o-c (o) -structure.
  • the rataton ring is counted as the first ring, and when only the rataton ring is present, it is called a monocyclic group, and when it has another ring structure, it is called a polycyclic group regardless of the structure.
  • any unit can be used without any particular limitation as long as it has both such a rataton structure (one O—C (O) —) and a cyclic group.
  • examples of the latatatone-containing monocyclic group include groups in which one hydrogen atom has been removed from ⁇ -petit-latatotone.
  • examples of the latathone-containing polycyclic group include groups in which one hydrogen atom has been removed from a bicycloalkane, tricycloalkane, or tetracycloalkane having a latathone ring.
  • a group obtained by removing one hydrogen atom from a latathone-containing tricycloalkane having the following structural formula is advantageous in that it is easily available industrially.
  • examples of the structural unit (a2) include structural units represented by the following general formulas (a2— :! to (a2-5).
  • R is the same as defined above, R ′ is a hydrogen atom, a lower alkyl group, or an alkoxy group having 1 to 5 carbon atoms, and m is an integer of 0 or 1.
  • R ' is preferably a hydrogen atom in view of industrial availability.
  • R ' is preferably a hydrogen atom in view of industrial availability.
  • resin component (A) as the structural unit (a2), one type may be used alone, or two or more types may be used in combination.
  • the resin component (A) is preferably a copolymer having both of these structural units (al) and (a2) because the effects of the present invention are excellent.
  • the resin component (A) is further an acrylate ester containing a polar group-containing aliphatic hydrocarbon group.
  • a structural unit ( a 3) By having the structural unit (a3), the hydrophilicity of the component (A) is increased, the affinity with the developer is increased, the alkali solubility in the exposed area is improved, and the resolution is improved. .
  • Examples of the polar group include a hydroxyl group, a cyano group, a carboxy group, and a hydroxyalkyl group substituted with a partial force S fluorine atom of an alkyl group, and a hydroxyl group is particularly preferred.
  • aliphatic hydrocarbon group examples include linear or branched hydrocarbon groups having 1 to 10 carbon atoms (preferably alkylene groups), and polycyclic aliphatic hydrocarbon groups (polycyclic groups). Can be mentioned.
  • polycyclic group for example, many resins proposed for resists for ArF excimer laser resist compositions can be appropriately selected and used.
  • the structural unit is more preferable.
  • the polycyclic group include groups in which one or more hydrogen atoms have been removed from bicycloalkane, tricycloalkane, tetracycloalkane, or the like.
  • Specific examples include groups in which one or more hydrogen atoms have been removed from a polycycloalkane such as adamantane, norbornane, isobornane, tricyclodecane or tetracyclododecane.
  • a polycycloalkane such as adamantane, norbornane, isobornane, tricyclodecane or tetracyclododecane.
  • Such polycyclic groups can be appropriately selected and used for the polymers (resin components) for resist compositions for ArF excimerizers, which have been proposed in large numbers.
  • a group obtained by removing two or more hydrogen atoms from adamantane a group obtained by removing two or more hydrogen atoms from norbornane, or a group obtained by removing two or more hydrogen atoms from tetracyclododecane. Is industrially preferred.
  • the hydrocarbon group in the polar group-containing aliphatic hydrocarbon group is a carbon group.
  • the hydroxyethyl ester force of acrylic acid is preferred as a structural unit to be derived.
  • the hydrocarbon group is a polycyclic group, Preferred are a structural unit represented by the formula (a3-1), a structural unit represented by (a3-2), and a structural unit represented by (a3-3).
  • j is preferably 1 or 2, and more preferably 1; When j is 2, it is preferable that the hydroxyl group is bonded to the 3rd and 5th positions of the adamantyl group. When j is 1, it is preferable that the hydroxyl group is bonded to the 3-position of the adamantyl group.
  • k is preferably 1.
  • the cyan group is preferably bonded to the 5th or 6th position of the norbornyl group.
  • t ′ is preferably 1.
  • 1 is preferably 1.
  • s is preferably 1.
  • These preferably have a 2-norbornyl group or a 3-norbornyl group bonded to the terminal of the carboxy group of acrylic acid.
  • the fluorinated alkyl alcohol is preferably bonded to the 5th or 6th position of the norbornyl group.
  • one type may be used alone, or two or more types may be used in combination. May be.
  • the proportion of the structural unit (a3) in the resin component (A) is 5 to 50 mol with respect to all the structural units constituting the resin component (A). %, More preferably 15 to 45 mol%, most preferably 15 to 35 mol%.
  • the resin component (A) may contain other structural units (a4) other than the structural units (al) to (a3) as long as the effects of the present invention are not impaired.
  • the structural unit (a4) is not classified into the structural units (al) to (a3) described above, and is not particularly limited as long as it is other structural units.
  • KrF excimer laser preferably ArF
  • resist resins such as excimer lasers.
  • the structural unit (a4) for example, a structural unit that contains a non-acid-dissociable aliphatic polycyclic group and is induced by the power of acrylate ester is preferable.
  • the polycyclic group are the same as those exemplified in the case of the structural unit (al), for ArF excimer laser, for KrF excimer laser (preferably for ArF excimer laser).
  • a number of hitherto known materials can be used for the resin component of the resist composition.
  • At least one selected from a tricyclodecanyl group, an adamantyl group, a tetracyclododecanyl group, an isobornyl group, and a norbornyl group is preferable in terms of industrial availability.
  • These polycyclic groups may be substituted with a linear or branched alkyl group having 1 to 5 carbon atoms.
  • the structural unit (a4) is not an essential component of the resin component (A), but when it is contained in the resin component (A), all the structural units constituting the resin component (A) the total of 1 to 30 moles the configuration unit (a4) 0/0, and preferably to 10 to 20 mole 0/0 contained preferably.
  • the resin component (A) is obtained by polymerizing a monomer that derives each structural unit by a known radical polymerization using a radical polymerization initiator such as azobisisobutyronitrile (AIBN).
  • AIBN azobisisobutyronitrile
  • the resin component (A) has a hydroxyl group bonded to a carbon atom at the polymer terminal, and the carbon atom at the top of the hydroxyl group has a terminal structure having at least one electron-withdrawing group. preferable.
  • Examples of the electron-withdrawing group include a halogen atom and a halogenialkyl group. I can get lost.
  • halogen atom examples include a fluorine atom and a chlorine atom.
  • a fluorine atom is preferred.
  • the halogen is the same as the halogen atom.
  • the alkyl group is preferably a lower alkyl group having, for example, about 1 to 3 carbon atoms, preferably a methyl group or an ethyl group, and most preferably a methyl group.
  • a force that includes a trifluoromethylino group, a difluoromethyl group, a monofluoromethyl group, a perfluoroethyl group, and the like, particularly a trifluoromethyl group is preferable.
  • the number of electron-withdrawing groups is 1 or 2, preferably 2.
  • R 1 and R 2 each independently represents an alkyl group, a halogen atom, or a halogenated alkyl group, at least one of which is an electron-withdrawing group selected from a halogen atom or a halogenated alkyl group Can be expressed as
  • the halogen atom or halogenated alkyl group here is the same as described above, and examples of the alkyl group include lower alkyl groups such as a methyl group, an ethyl group, and a propyl group.
  • the electron-withdrawing group is preferably a fluorine atom or a fluorinated alkyl group as described above, particularly when R 1 and R 2 are both fluorinated alkyl groups, particularly trifluoromethyl groups. It is also excellent in the effect of reducing LER (line edge roughness: uneven unevenness of the line side wall).
  • the structural unit (Ml) having a CI ⁇ I ⁇ OH group (hereinafter, this group may be referred to as a "terminal structure") bonded to the polymer terminal.
  • the proportion is 1 mol% or more (preferably 2 mol% or more) with respect to the total 100 mol% of the structural units other than the structural unit (Ml) among all the structural units constituting the resin component (A).
  • the total of the structural units other than the structural unit (Ml) includes, for example, structural units derived from known polymerization initiators such as azobisisoptyronitrile (AIBN) used in radical polymerization. Units derived from the monomer.
  • the upper limit value is not particularly limited, but it is practically 5 The mol% or less. In addition, by setting it to 1 mol% or more, the effect of reducing development defects and improving LER by introducing a terminal structure is excellent. Below this, these effects tend to be inferior.
  • the number of moles of the structural unit (Ml) is equal to the number of moles of the terminal structure and the number of moles of the hydroxyl group.
  • the terminal structure is introduced into one end of the polymer by adding a chain transfer agent having a -CI ⁇ R ⁇ H group, for example, when a polymer is produced by radical polymerization using a monomer and a polymerization initiator. can do.
  • the structural unit (Ml) having the terminal structure is a structural unit (Ml) derived from this chain transfer agent.
  • the chain transfer agent is represented by, for example, a general formula “X_R ′ ⁇ ⁇ ⁇ 2 0 ⁇ ”.
  • X represents a hydroxyl group or a thiol group
  • the chain transfer agent is bonded to the polymer terminal by elimination of a hydrogen atom of the hydroxyl group or thiol group. Therefore, in this case, the structural unit (Ml) is a unit obtained by removing a hydrogen atom from the hydroxyl group or thiol group of X in X_R'-CR ' ⁇ OHJ. From the point of reactivity, X is a thiol group. Is preferred.
  • R ′ in X—R′—CR′R′OHj is a divalent aliphatic hydrocarbon group (which may be linear, branched or cyclic) or a divalent aromatic hydrocarbon group, Of these, a linear or branched aliphatic hydrocarbon group is preferred.
  • Examples of the alicyclic group include a cyclohexylene group.
  • Examples of the aromatic hydrocarbon group include a p-phenylene group.
  • linear or branched aliphatic hydrocarbon group examples include a methylene group, an ethylene group, an n-propylene group, and an isopropylene group.
  • An ethylene group and an n-propylene group are preferable.
  • the general formula of the preferred chain transfer agent is SH_ (CH) -C (CF) _OH (m is 2
  • the preferred structural unit (Ml) is — S _ (CH) -C (CF)
  • the ratio of the terminal structure (the ratio of the structural unit (Ml)) can be adjusted by adjusting the amount of charged monomer and the amount of the chain transfer agent, or adjusting the timing of adding the chain transfer agent. By adjusting the mass average molecular weight of the resin for the dyst composition, it can be changed. Further, in the resin for resist composition after synthesis, the number of moles of the terminal structure (number of moles of the structural unit (Ml)) is measured by NMR (nuclear magnetic resonance spectrum) such as proton-NMR and carbon NMR. be able to.
  • NMR nuclear magnetic resonance spectrum
  • the mass average molecular weight (Mw) of the resin component (A) is not particularly limited, but 2000 to 50000 is preferable, and 3000 to 30000 force S. More preferably, 5000 to 20000 most preferred. If it is smaller than the upper limit of this range, it has sufficient solubility in a resist solvent to be used as a resist, and the dry etching resistance and resist pattern cross-sectional shape which are larger than the lower limit of this range are good.
  • the degree of dispersion (Mw / Mn) f is preferably 1.0 to 5.0, more preferably 1.0 to 3.0 force S, and most preferably 1.2 to 2.5.
  • the acid generator (B2) is used as an essential component.
  • R 1 ′′ represents an alkyl group, an alkoxy group, a halogen atom, or a hydroxyl group
  • n represents 0 or an integer of 1 to 3.
  • the plurality of R 1 ′′ may be the same as or different from each other.
  • the alkyl group as R 1 ′′ is most preferably a methyl group, an ethynole group, a propyl group, an n-butyl group or a tert-butyl group, preferably an alkyl group having 1 to 5 carbon atoms.
  • the alkoxy group as R 1 ′′ is most preferably a methoxy group or an ethoxy group, preferably an alkoxy group having 1 to 5 carbon atoms.
  • the halogen atom as R 1 ′′ is preferably a fluorine atom.
  • N is preferably 0 or 1, more preferably 0.
  • R 2 ′′ and R 3 ′′ each independently represents a reelyl group or an alkyl group, which may have a substituent.
  • the aryl group as R 2 "and R 3 " is not particularly limited, for example, an aryl group having 6 to 20 carbon atoms, and in the aryl group, part or all of the hydrogen atoms are alkyl groups, alkoxy groups. It may not be substituted with a group, a halogen atom, a hydroxyl group or the like.
  • an aryl group having 6 to 10 carbon atoms is preferable because it can be synthesized at a low cost. Specific examples include a phenyl group and a naphthyl group.
  • the alkyl group as the substituent is the same as the alkyl group as the R 1 ′′.
  • the alkoxy group as the substituent is the same as the alkoxy group as R 1 ′′.
  • the halogen atom as the substituent is the same as the halogen atom as R 1 ′′.
  • the alkyl group as “, R 3 ” is not particularly limited, and examples thereof include linear, branched or cyclic alkyl groups having 1 to 10 carbon atoms. From the viewpoint of excellent resolution, the number of carbon atoms is preferably 1 to 5. Specifically, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, n-pentyl group, cyclopentyl group, hexyl group, cyclohexyl group, noninore group, decanyl group A methyl group is preferable because it is excellent in resolution and can be synthesized at low cost. Most preferably, R 2 ′′ and R 3 ′′ are both phenyl groups.
  • the anion part in the component (B1) is not particularly limited, and those known as the anion part of the onion salt-based acid generator can be appropriately used.
  • R 4 SO— (R 4 ”represents a linear, branched or cyclic alkyl group or fluorine.
  • R 4 SO _ "
  • R 4 represents a linear, branched or cyclic alkyl group.
  • Or represents a fluorinated alkyl group.
  • the alkyl group as R 4 ′′ has 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms, more preferably 1 to 4 carbon atoms.
  • the cyclic alkyl group as R 4 ′′ is the cyclic group shown as the above “, R 3 ”, and preferably has 4 to 15 carbon atoms, preferably 4 to 10 carbon atoms. Is more preferably 6 to 10 carbon atoms.
  • the fluorinated alkyl group as R 4 ′′ preferably has 1 to 10 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 4 carbon atoms, and most preferably 1 to 4 carbon atoms.
  • the fluorination rate of the alkyl fluoride group (ratio of fluorine atoms in the alkyl group) is preferably 10 to 100%, more preferably 50 to 100%, and in particular, all hydrogen atoms are fluorine atoms. Replaced by force This is preferable because the strength of the acid increases.
  • R 4 ′′ is most preferably a linear or cyclic alkyl group or a fluorinated alkyl group.
  • X is a linear or branched alkylene group in which at least one hydrogen atom is replaced with a fluorine atom, and the alkylene group has 2 carbon atoms. -6, preferably 3-5 carbon atoms, most preferably 3 carbon atoms.
  • Y ′′ and ⁇ ′′ are each independently a linear or branched alkyl group in which at least one hydrogen atom is substituted with a fluorine atom, and the number of carbon atoms of the alkyl group Is 1 to: 10, preferably 1 to 7 carbon atoms, more preferably 1 to 3 carbon atoms.
  • the carbon number of the alkylene group of X ′′ or the carbon number of the alkyl group of “ ⁇ ⁇ ⁇ ⁇ ” and “ ⁇ ” is preferably as small as possible within the range of the above-mentioned carbon number for reasons such as good solubility in a resist solvent.
  • the ratio of fluorine atoms, that is, the fluorination rate is preferably 70 to 100%, more preferably 90 to 100%, and most preferably perfluorocarbons in which all hydrogen atoms are replaced with fluorine atoms.
  • an anion part of the component (B1) an anion part represented by a general formula "R 4 " S0_ "
  • R 4 ′′ is a fluorinated alkyl group.
  • R 21 ′ represents an organic group
  • R 22 ′ represents a monovalent organic group or a cyano group
  • the organic group is a group containing a carbon atom, and an atom other than a carbon atom (for example, a hydrogen atom, an oxygen atom, a nitrogen atom, a sulfur atom, a halogen atom (fluorine atom, chlorine atom, etc.), etc.). You may have.
  • the organic group as R 21 ′ is preferably a linear, branched or cyclic alkyl group or aryl group. These alkyl groups and aryl groups may have a substituent.
  • the substituent is not particularly limited, and examples thereof include a fluorine atom and a linear, branched or cyclic alkyl group having 1 to 6 carbon atoms.
  • “having a substituent” means that part or all of the hydrogen atoms of the alkyl group or aryl group are substituted with a substituent.
  • carbon number 1 to 20 is preferable. Carbon number 10 is more preferable. Carbon number 1 to 8 is more preferable. Carbon number 1 to 6 is particularly preferable. Is most preferred.
  • a partially or completely halogenated alkyl group (hereinafter sometimes referred to as a halogenated alkyl group) is particularly preferable.
  • a partially halogenated alkyl group means an alkyl group in which some of the hydrogen atoms are replaced with halogen atoms, and a fully halogenated alkyl group means that all of the hydrogen atoms are An alkyl group substituted with a halogen atom.
  • the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is particularly preferable. That is, the halogenated alkyl group is preferably a fluorinated alkyl group.
  • the aryl group preferably has 4 to 20 carbon atoms, preferably 4 to 10 carbon atoms, and more preferably 6 to 10 carbon atoms.
  • a partially or completely halogenated aryl group is particularly preferable.
  • a partially halogenated aryl group means an aryl group in which a part of the hydrogen atom is replaced with a halogen atom, and a fully halogenated aryl group means that all the hydrogen atoms are halogenated.
  • R 21 ′ is particularly preferably an alkyl group having 1 to 4 carbon atoms having no substituent or a fluorinated alkyl group having 1 to 4 carbon atoms.
  • the organic group as R ⁇ ' is preferably a linear, branched or cyclic alkyl group, aryl group or cyano group.
  • Examples of the alkyl group and aryl group for R 22 ′ include the same alkyl groups and aryl groups as those described above for R 21 ′.
  • R 22 ′ is particularly preferably a cyano group, an alkyl group having 1 to 8 carbon atoms having no substituent, or a fluorinated alkyl group having 1 to 8 carbon atoms.
  • the component (B2) is more preferably a compound represented by the following general formula (B-2) or (B-3).
  • R dl represents a cyano group, an alkyl group having no substituent, or
  • R 32 is an aryl group.
  • R 33 is an alkyl group having no substituent or a halogenated alkyl group.
  • R d4 represents a cyano group, an alkyl group having no substituent, or a halogenated alkyl group.
  • R 35 is a divalent or trivalent aromatic hydrocarbon group.
  • R 36 is an alkyl group having no substituent or a halogenated alkyl group.
  • p is 2 or 3.
  • alkyl or halogenated alkyl group which includes no substituent R 31 is 1 to carbon atoms: preferably from 10 member carbon atoms 1-8 Is more preferred. Carbon number 1 to 6 is most preferred.
  • R 31 is more preferably a fluorinated alkyl group, preferably a halogenated alkyl group.
  • the fluorinated alkyl group in R dl preferably has 50% or more of the hydrogen atom of the alkyl group, more preferably 70% or more, and even more preferably 90% or more. .
  • the aryl group of R 32 is a hydrogen atom from an aromatic hydrocarbon ring such as a phenyl group, a biphenylyl group, a fluorenyl group, a naphthyl group, an anthracyl group, or a phenanthryl group. And a heteroaryl group in which a part of the carbon atoms constituting the ring of these groups is substituted with a heteroatom such as an oxygen atom, a sulfur atom or a nitrogen atom. Among these, a fluorenyl group is preferable.
  • the aryl group of R 32 may have a substituent such as an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group, or an alkoxy group.
  • the alkyl group or halogenated alkyl group in the substituent preferably has 1 to 4 carbon atoms, more preferably 1 to 4 carbon atoms.
  • the halogenated alkyl group is preferably a fluorinated alkyl group.
  • the alkyl group or halogenialkyl group having no substituent of R 33 has a carbon number of:
  • R 33 is preferably a fluorinated alkyl group, more preferably a halogenated alkyl group.
  • the fluorinated alkyl group for R 33 preferably has a hydrogen atom of the alkyl group of 50% or more, more preferably 70% or more, and still more preferably 90% or more. This is preferable because the strength of the generated acid is increased. Most preferably, it is a fully fluorinated alkyl group in which a hydrogen atom is 100% fluorine-substituted.
  • Examples of the divalent or trivalent aromatic hydrocarbon group for R 35 include groups obtained by further removing one or two hydrogen atoms from the aryl group for R 32 .
  • the alkyl group or Harogeni spoon alkyl group, et al include the same alkyl group or halogenated alkyl group which includes no substituent of the 3 It is.
  • p is preferably 2.
  • component (B2) examples include ⁇ - ( ⁇ -toluenesulfonyloxymino) -benzyl cyanide, H- ( ⁇ -chlorobenzenebenzenesulfonyloxymino) -benzylcyanide, H- (4- 2-trobenzenesulfonyloxymino) -benzylcyanide, H- (4-nitro-2-trifluoromethylbenzenesulfonyloxymino) -benzylcyanide, H- (benzenesulfonoxyximino) -4-chloro Methyl benzyl cyanide, bis- (benzenesulfonyloxyimino) -2,4-dichlorobenzyl cyanide, bis- (benzenesulfonyloxyximino) -2,6-dichlorobenzylcyanide, bis- (benzenesulfonyl) 4-methoxybenzyl cyanide,
  • CH3-C N-OS0 2- (CH2 ⁇ 3 CH3
  • Mass of content of component (Bl) and component (B2) in the positive resist composition of the present invention it (B1): ( ⁇ 2) ⁇ , 10: 90-90: 10 is preferred, 25: 75 to 75: 25 force S is more preferable, and 40: 60-60: 40 is more preferable.
  • mass ratio of the component (B1) to the component (2) is within the above range, the characteristics of the pattern shape, EL margin, and dimensional fidelity can be improved.
  • the content of the component (B1) in the positive resist composition of the present invention is preferably 1 to 10 parts by mass with respect to 100 parts by mass of the component (ii), more preferably 3 to 7 parts by mass. 5-7 parts by mass is preferable for the force.
  • a sufficient effect can be obtained by setting the content of the component (B1) to be not less than the lower limit of the above range.
  • the content of the component ( ⁇ 2) in the positive resist composition of the present invention is preferably 1 to 10 parts by mass with respect to 100 parts by mass of the component ( ⁇ ), and more preferably 2 to 8 parts by mass. 3 to 7 parts by mass is preferable.
  • a sufficient effect can be obtained by setting the content of the component (ii) above the lower limit of the above range.
  • the upper limit of the above range is preferable.
  • one or more acid generator components other than the component (B1) and the component ( ⁇ 2) may be contained.
  • the other acid generator component is particularly limited. It is not specified, and it is possible to use what has been proposed as an acid generator for chemically amplified resists.
  • onium salt-based acid generators such as sulfonium salt and jordonium salt, oxime sulfonate-based acid generators, bisalkyl or bisarylsulfonyldithione, which are not included in the components (B1) and (B2).
  • diazomethane acid generators such as azomethanes and poly (bissulfonyl) diazomethanes, nitrobenzil sulfonate acid generators, iminosulfonate acid generators, and disulfone acid generators are known. Yes.
  • the total content of the component (B) in the positive resist composition of the present invention is preferably 2 to 20 parts by mass with respect to 100 parts by mass of the component (A) 5 to 15 parts by mass is more preferable. 8 to 14 parts by mass is most preferable. By setting it within the above range, pattern formation is sufficiently performed and good characteristics can be obtained. Moreover, since a uniform solution is obtained and storage stability becomes favorable, it is preferable.
  • the proportion of the total of component (B1) and component (B2) is preferably 50% by mass or more, more preferably 75% by mass or more, and most preferably 100% by mass.
  • the positive resist composition of the present invention is further optional in order to improve the resist pattern shape, post exposure stability of the latent image formed by the pattern-wise exposure of the resist layer, etc. It is possible to add nitrogen-containing organic compound (D) as a component.
  • any known one may be used, but aliphatic amines, particularly secondary aliphatic amines and tertiary aliphatic amines are preferred. .
  • Aliphatic amines contain at least one hydrogen atom of ammonia NH and have 12 or more carbon atoms.
  • Examples include amines substituted with the lower alkyl group or hydroxyalkyl group (alkylamines or alkylalcoholamines). Specific examples thereof include Kishiruamin to n-, n- Hepuchiruamin, n- Otachinoreamin, n- Noniruamin, mono Arukiruamin such n- Deshiruamin; Jechiruamin, di _ n - Puropiruamin, di - n- Hepuchiruamin, di _n- Okuchiruamin, Dialkylamines such as dicyclohexylamine; trimethylamine , Triethylamine, tri-n-propylamine, tri-n-butylamine, tri-n-hexylamine, tri-n-pentylamine, tri-n-ptyluamine, tri-n-octylamine, tri-n-noeramine, tri-n-decanylamine, Trial
  • Component (D) is usually used in the range of 0.01 to 5.0 parts by mass per 100 parts by mass of component (A).
  • the positive resist composition of the present invention prevents the deterioration of sensitivity due to the blending of the component (D), and the resist pattern shape and stability over time (post exposure stability of the latent image formed oy the pattern-wise).
  • an organic carboxylic acid or phosphorus oxoacid or derivative thereof) (referred to as component (E) in this specification) can be added as an optional component.
  • the component (D) and the component (E) can be used in combination, or one type of restraining force can be used.
  • organic carboxylic acid for example, malonic acid, citrate, malic acid, succinic acid, benzoic acid, salicylic acid and the like are suitable.
  • Phosphoric acid or its derivatives include phosphoric acid, phosphoric acid di_n_butyl ester, phosphoric acid diphenyl ester and other phosphoric acid or derivatives such as those esters; phosphonic acid, phosphonic acid dimethyl ester, phosphonic acid Phosphonic acid such as n-butyl ester, phenyl phosphonic acid, diphenylenoestenole phosphonate, dibenenoreestenole phosphonate, and derivatives thereof; phosphines such as phosphinic acid and phenylphosphinic acid Derivatives such as acids and their esters are mentioned, among which phosphonic acid is particularly preferred.
  • Component (E) is used in a ratio of 0.01 to 5.0 parts by mass per 100 parts by mass of component (A).
  • the positive resist composition of the present invention can be produced by dissolving the material in an organic solvent.
  • organic solvent it is only necessary to dissolve each component to be used so that a uniform solution can be obtained. Two or more kinds can be appropriately selected and used.
  • latones such as ⁇ -butyrate rataton; ketones such as acetone, methyl ethyl ketone, cyclohexanone, methyl isoamyl ketone, 2_heptanone; ethylene glycol, ethylene glycol monoacetate, diethylene glycol, Polyethylene alcohols such as diethylene glycol monoacetate, propylene glycol, propylene glycol monoacetate, dipropylene glycol, or monomethyl ether, monoethyl ether, monopropyl ether, monobutyl ether or monophenyl ether of dipropylene glycol monoacetate and the like Derivatives; cyclic ethers such as dioxane; methyl lactate, ethyl lactate (EL), methyl acetate, ethyl acetate, butyl acetate, methyl pyruvate, pyrubi Examples thereof include esters such as ethyl acetate, methyl methoxypropionate,
  • organic solvents may be used alone or as a mixed solvent of two or more.
  • a mixed solvent obtained by mixing propylene glycol monomethyl ether acetate (PGMEA) and a polar solvent is preferable.
  • the mixing ratio may be appropriately determined in consideration of the compatibility between PGMEA and the polar solvent, preferably 1: 9 to 9: 1, more preferably 2: 8 to 8: 2. It is preferable to be within the range.
  • the mass ratio of PGMEA: EL is preferably 1: 9 to 9: 1, more preferably 2: 8 to 8: 2.
  • a mixed solvent of at least one selected from PGMEA and EL and ⁇ -petit-mouth rataton is also preferable.
  • the mixing ratio of the former and the latter is preferably 70:30 to 95: 5.
  • the amount of organic solvent used is not particularly limited.
  • the solid content concentration of the resist composition is generally 2 to 20% by mass, preferably 5 to 15% by mass.
  • the positive resist composition of the present invention may further contain, if desired, miscible additives such as an additional resin for improving the performance of the resist film, a surfactant for improving coatability, and a dissolution inhibitor.
  • miscible additives such as an additional resin for improving the performance of the resist film, a surfactant for improving coatability, and a dissolution inhibitor.
  • Plasticizers, stabilizers, colorants, antihalation agents, dyes, and the like can be appropriately added and contained.
  • the resist pattern forming method of the present invention can be performed, for example, as follows. That is, first, the positive resist composition is applied onto a substrate such as silicon wafer with a spinner or the like, and a pre-beta is applied for 40 to 120 seconds under a temperature condition of 80 to 150 ° C, preferably 60. Apply for ⁇ 90 seconds to form a resist film.
  • the resist film is selectively exposed with a single ArF excimer laser beam through a desired mask pattern using, for example, an ArF exposure apparatus or the like, and then subjected to PEB (after exposure at a temperature of 80 to 150 ° C. (Heating) is applied for 40 to 120 seconds, preferably 60 to 90 seconds.
  • alkali developing solution for example, 0. 1: developing is conducted using 10 weight 0/0 tetramethylammonium Niu arm hydrate port Kishido solution. If necessary, post-beta may be applied after development processing.
  • An organic or inorganic antireflection film may be provided between the substrate and the coating layer of the resist composition.
  • the wavelength used for the exposure is not particularly limited, ArF excimer laser, KrF excimer laser, F excimer laser, EUV (extreme ultraviolet), VUV (vacuum ultraviolet), EB (electron beam),
  • the positive resist composition which is effective in the present invention is particularly effective for an ArF excimer laser.
  • the EL margin and the dimensional fidelity can be improved.
  • the resist pattern is less likely to fall down, and the line edge roughness (LER) in which the surface of the side wall of the line pattern is not uniform is also improved.
  • the component (B1) has a substituent derived from naphthalene in the cation portion, and therefore, in the exposure wavelength band, compared to the acid generator component comprising a triphenylsulfonium-based onium salt. If the light absorption is suppressed and the exposure amount is the same, the acid generation amount per mole of the acid generator component is considered to be suppressed. In particular, it is speculated that the absorption of light is effectively suppressed in the wavelength band of the ArF excimer laser (especially the transparency of ArF excimer laser light is improved).
  • the combination of the component (B1) and the component (B2), which is an oxime sulfonate acid generator, simultaneously achieves the above-described plurality of good characteristics due to the synergistic effect of both. It is considered possible.
  • the component (B) is represented by 6.0 parts by mass of the compound represented by the chemical formula (bl-01) and the chemical formula (b2-01).
  • a positive resist composition having a solid content concentration of about 9% by mass was prepared.
  • an organic antireflection film composition “AR_46” (trade name, manufactured by Shipley Co., Ltd.) was applied onto an 8-inch silicon wafer using a spinner, and 225 ° C. on a hot plate. By baking for 60 seconds and drying, an organic antireflection film with a film thickness of 29 nm was formed. Then, the positive resist composition is applied onto an antireflection film using a spinner, pre-beta (PAB) at 105 ° C. for 60 seconds on a hot plate, and dried to form a resist layer having a thickness of 200 nm. Formed.
  • PAB pre-beta
  • l L / S pattern was formed using lOnm and 130nm line and space mask pattern, and MEF (mask error factor) value was calculated from the following equation.
  • CD and CD are 130nm and lOnm respectively.
  • the resist pattern width (nm) of the formed L & S pattern. MD and MD are the resist pattern width (nm) of the formed L & S pattern. MD and MD are the resist pattern width (nm) of the formed L & S pattern. MD and MD are the resist pattern width (nm) of the formed L & S pattern. MD and MD are the resist pattern width (nm) of the formed L & S pattern. MD and MD are the resist pattern width (nm) of the formed L & S pattern. MD and MD are
  • Example 1 the ( ⁇ ) component was changed to 6.0 parts by mass of the compound represented by the above chemical formula (b2-01) and 2.0 parts by mass of triphenylsulfonium nonafluorobutane sulfonate.
  • an L / S pattern was formed in the same manner as in Example 1 and the same evaluation was performed. The results are shown in Table 1 below.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Materials For Photolithography (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)

Abstract

La présente invention concerne une composition de résist positif présentant une fidélité dimensionnelle et un écart EL améliorés (linéarité du masque). Cette composition de résist positif comprend un composant de résine (A) dont la solubilité alcaline est augmentée grâce à l’action d’un acide, et un composant générateur d’acide (B) qui produit un acide lors d’une exposition à la lumière. Le composant (B) comprend un agent générateur d’acide (B1) à base de sel d'onium présentant une partie cationique représentée par la formule générale (b-1) et un agent générateur d’acide (B2) à base de sulfate d’oxime de structure générale (b-2). Formule (b-1) dans laquelle R1' représente un groupe alkyle, un groupe alcoxy, un atome d’halogène ou un groupe hydroxyle, R2' et R3' représentent chacun indépendamment un groupe alkyle ou aryle éventuellement substitué et n est un nombre entier allant de 0 à 3. Formule (b-2) dans laquelle R21' représente un groupe organique et R22' représente un groupe organique monovalent ou un groupe cyano.
PCT/JP2005/020419 2004-12-17 2005-11-08 Composition de resistpositif et procede de formation d’un motif de resist WO2006064622A1 (fr)

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US7488568B2 (en) 2007-04-09 2009-02-10 Tokyo Ohka Kogyo Co., Ltd. Resist composition, method of forming resist pattern, compound and acid generator
JP5066405B2 (ja) 2007-08-02 2012-11-07 富士フイルム株式会社 電子線、ｘ線又はｅｕｖ用レジスト組成物及び該組成物を用いたパターン形成方法
JP5393325B2 (ja) * 2008-08-01 2014-01-22 富士フイルム株式会社 ポジ型レジスト組成物及びそれを用いたパターン形成方法
JP5422293B2 (ja) * 2008-08-01 2014-02-19 富士フイルム株式会社 ポジ型レジスト組成物及びそれを用いたパターン形成方法
JP5548406B2 (ja) * 2008-08-22 2014-07-16 東京応化工業株式会社 ポジ型レジスト組成物、レジストパターン形成方法、高分子化合物
JP5470053B2 (ja) 2010-01-05 2014-04-16 東京応化工業株式会社 ポジ型レジスト組成物、レジストパターン形成方法
JP6002378B2 (ja) 2011-11-24 2016-10-05 東京応化工業株式会社 高分子化合物の製造方法
US8795948B2 (en) 2012-03-22 2014-08-05 Tokyo Ohka Kogyo Co., Ltd. Resist composition, method of forming resist pattern and polymeric compound
US8795947B2 (en) 2012-03-22 2014-08-05 Tokyo Ohka Kogyo Co., Ltd. Resist composition and method of forming resist pattern

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JPH11236416A (ja) * 1997-10-08 1999-08-31 Shin Etsu Chem Co Ltd ポリスチレン系高分子化合物及び化学増幅ポジ型レジスト材料並びにパターン形成方法
JP2004334060A (ja) * 2003-05-12 2004-11-25 Shin Etsu Chem Co Ltd 化学増幅型レジスト用光酸発生剤及びそれを含有するレジスト材料並びにパターン形成方法
JP2004341062A (ja) * 2003-05-13 2004-12-02 Fuji Photo Film Co Ltd ポジ型レジスト組成物
JP2004354954A (ja) * 2003-03-28 2004-12-16 Tokyo Ohka Kogyo Co Ltd ホトレジスト組成物及びそれを用いたレジストパターン形成方法

Patent Citations (4)

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JPH11236416A (ja) * 1997-10-08 1999-08-31 Shin Etsu Chem Co Ltd ポリスチレン系高分子化合物及び化学増幅ポジ型レジスト材料並びにパターン形成方法
JP2004354954A (ja) * 2003-03-28 2004-12-16 Tokyo Ohka Kogyo Co Ltd ホトレジスト組成物及びそれを用いたレジストパターン形成方法
JP2004334060A (ja) * 2003-05-12 2004-11-25 Shin Etsu Chem Co Ltd 化学増幅型レジスト用光酸発生剤及びそれを含有するレジスト材料並びにパターン形成方法
JP2004341062A (ja) * 2003-05-13 2004-12-02 Fuji Photo Film Co Ltd ポジ型レジスト組成物

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