[go: up one dir, main page]

WO2006011420A1 - Nouveau composé, composé de polymère, composition de résist et procédé pour former un motif de résist - Google Patents

Nouveau composé, composé de polymère, composition de résist et procédé pour former un motif de résist Download PDF

Info

Publication number
WO2006011420A1
WO2006011420A1 PCT/JP2005/013473 JP2005013473W WO2006011420A1 WO 2006011420 A1 WO2006011420 A1 WO 2006011420A1 JP 2005013473 W JP2005013473 W JP 2005013473W WO 2006011420 A1 WO2006011420 A1 WO 2006011420A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
alkyl group
polymer compound
structural unit
atom
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2005/013473
Other languages
English (en)
Japanese (ja)
Inventor
Daiju Shiono
Syogo Matsumaru
Hideo Hada
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Tokyo Ohka Kogyo Co Ltd
Original Assignee
Tokyo Ohka Kogyo Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Tokyo Ohka Kogyo Co Ltd filed Critical Tokyo Ohka Kogyo Co Ltd
Publication of WO2006011420A1 publication Critical patent/WO2006011420A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/90—Carboxylic acid amides having nitrogen atoms of carboxamide groups further acylated
    • C07C233/91—Carboxylic acid amides having nitrogen atoms of carboxamide groups further acylated with carbon atoms of the carboxamide groups bound to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/24—Derivatives of thiourea containing any of the groups, X being a hetero atom, Y being any atom
    • C07C335/26—Y being a hydrogen or a carbon atom, e.g. benzoylthioureas
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/52—Amides or imides
    • C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
    • G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • Novel compound, polymer compound, resist composition and resist pattern forming method Novel compound, polymer compound, resist composition and resist pattern forming method
  • the present invention relates to a novel compound, a polymer compound having a novel structural unit, a resist composition using the polymer compound, and a resist pattern forming method using the resist composition.
  • 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 that generates an acid upon exposure is known.
  • Patent Document 1 discloses a structural unit derived from a (meth) acrylate ester group having an acid dissociable, dissolution inhibiting group in an ester moiety, and a (meth) having a rataton skeleton such as a ⁇ -petit mouth rataton skeleton in the ester part.
  • Acrylic ester force A structural unit derived from a polymer having a structural unit derived from a (meth) acrylate ester having a polycyclic group containing a polar group such as a hydroxyl group in the ester portion has been proposed. Yes.
  • Patent Document 1 Japanese Patent Laid-Open No. 2003-167347
  • the present invention has been made in view of the above circumstances, and includes a polymer compound that can constitute a high-resolution resist composition, a compound suitable for producing the polymer compound, and the polymer compound. It is an object of the present invention to provide a resist composition containing the resist composition and a method for forming a resist pattern using the resist composition.
  • the present invention employs the following configuration.
  • a first aspect of the present invention is a compound represented by the following general formula (1).
  • R is a hydrogen atom or a lower alkyl group
  • X is a sulfur atom or an oxygen atom
  • Y is a carbon atom number 1 to which a part of the hydrogen atom may be substituted with a group containing a hetero atom; 20 chain, branched or cyclic alkyl groups, or a group in which a part of carbon atoms of the alkyl group is substituted with a heteroatom.
  • the second embodiment of the present invention has a structural unit (al) represented by the following general formula (al-1). It is a high molecular compound.
  • R is a hydrogen atom or a lower alkyl group; X is a sulfur atom or an oxygen atom; Y is a carbon atom number 1 to which a part of the hydrogen atom may be substituted with a group containing a hetero atom] 20 chain, branched or cyclic alkyl groups, or a group in which a part of carbon atoms of the alkyl group is substituted with a hetero atom.
  • the third aspect of the present invention is a resist composition
  • a rosin component (A) whose alkali solubility is changed by the action of an acid, and an acid generator component (B) which generates an acid upon exposure.
  • the resin component (A) is the polymer compound of the second embodiment.
  • the fourth aspect of the present invention includes a step of forming a resist film on a substrate using the resist composition of the third aspect, a step of exposing the resist film, and developing the resist film to form a resist pattern. It is a resist pattern formation method including the process of forming.
  • structural unit means a monomer unit constituting a polymer.
  • exposure is a concept including general radiation irradiation.
  • a polymer compound capable of constituting a high-resolution resist composition a compound suitable for producing the polymer compound, a resist composition containing the polymer compound, and A resist pattern forming method using the resist composition is obtained.
  • FIG. 1 is a graph showing the results of mask reality evaluation of Example 11 and Comparative Example 1. BEST MODE FOR CARRYING OUT THE INVENTION
  • the compound of the present invention (hereinafter sometimes referred to as compound (a)) has a structure represented by the above formula (1).
  • R is a hydrogen atom or a lower alkyl group.
  • the lower alkyl group is an alkyl group having 1 to 5 carbon atoms, and specifically includes a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, and a pentyl group.
  • a lower linear or branched alkyl group such as a group, an isopentyl group and a neopentyl group.
  • a methyl group is preferred.
  • X is a sulfur atom or an oxygen atom.
  • Y is a partial hydrogen atom substituted with a group containing a hetero atom !, may! /, A chain, branched or cyclic alkyl group having 1 to 20 carbon atoms, or the alkyl A part of the carbon atoms of the group is substituted with a heteroatom.
  • hetero atom examples include an oxygen atom, a sulfur atom, and a nitrogen atom.
  • Examples of the “chain, branched or cyclic alkyl group having 1 to 20 carbon atoms” include, for example, methyl group, ethyl group, n -propyl group, isopropyl group, n -butyl group, isobutyl group, tert -butyl group, pentyl A linear or branched alkyl group having 1 to 5 carbon atoms such as a group, isopentyl group or neopentyl group, a cyclic alkyl group having 4 to 6 carbon atoms such as a cyclopentyl group or a cyclohexyl group, or a combination thereof. Can be mentioned.
  • alkyl group means a monovalent saturated hydrocarbon group unless otherwise specified.
  • part of the hydrogen atoms may be substituted with a group containing a heteroatom (including a heteroatom itself)! /.
  • the “group containing a heteroatom” may be a heteroatom itself, or may be a group comprising a heteroatom and a carbon atom and Z or a hydrogen atom, such as an alkoxy group.
  • a hydrophilic group such as a hydroxyl group is excluded.
  • Examples of the "group in which part of the carbon atom of the alkyl group is substituted with a heteroatom! include an example in which the carbon atom is substituted with a nitrogen atom (for example, an alkyl having 2 or more carbon atoms).
  • examples of the compound (a) include compounds represented by the following general formula (2).
  • R is a hydrogen atom or a lower alkyl group
  • X is a sulfur atom or an oxygen atom
  • m is 0 or 1
  • Y ′ is substituted with a group in which a part of the hydrogen atoms includes a heteroatom.
  • R X in Formula (2) is the same as R X in Formula (1).
  • m is 0 or 1, more preferably 1.
  • Y ′ in formula (2) is the same as Y in formula (1) except that the alkyl group has 1 (20-m) carbon atoms.
  • R X is the same as X in Formula (1).
  • linear, branched or cyclic alkyl group of R 11 having 120 carbon atoms may be represented by the formula ( Examples are the same as the alkyl groups mentioned above for Y in 1) (having no heteroatoms).
  • R is a hydrogen atom or a lower alkyl group; ⁇ is a sulfur atom or an oxygen atom; and R 11 is a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms.
  • m is 1 includes a compound represented by the following general formula (4).
  • R and X are the same as R and X in formula (1).
  • N is an integer of 1 to 3, and is preferably 1 from the viewpoint of easy synthesis.
  • R 12 is the same as R 11 in the formula (3) except that the carbon number power ⁇ ⁇ (21 ⁇ 2n).
  • R is a hydrogen atom or a lower alkyl group; X is a sulfur atom or an oxygen atom; n is an integer of 1 to 3; R 12 is a straight chain of 1 to (21-2n) carbon atoms] , Branched or cyclic alkyl groups. ]
  • polymer compound (A1) has the structural unit (al) represented by the general formula (al-1) as an essential structural unit.
  • the structural unit (al) is a structural unit formed by cleavage of the ethylene double bond of the compound represented by the general formula (1).
  • R, X and Y in the general formula (al—l) are the same as X and Y in the general formula (1).
  • the structural unit (al) preferably includes a structural unit (al2) represented by the following general formula (al-2).
  • the structural unit (al2) is a structural unit formed by cleavage of the ethylene double bond of the compound represented by the general formula (2).
  • R, X, m, and Y 'in general formula (al-2) are the same as X, m, and Y' in general formula (2).
  • R is a hydrogen atom or a lower alkyl group
  • X is a sulfur atom or an oxygen atom
  • m is 0 or 1
  • Y ′ is substituted with a group in which a part of the hydrogen atoms includes a heteroatom.
  • the structural unit (al2) includes a structural unit (al3) represented by the following general formula (al-3) and a structural unit (al4) represented by Z or the following general formula (al-4) I prefer that.
  • one General formula (al-3) :! — Get lost! ⁇ ! ⁇ ! ⁇ Is the same as R, X, 1 , n, R 12 in the general formulas) and (4).
  • R represents a hydrogen atom or a lower alkyl group
  • X represents a sulfur atom or an oxygen atom
  • R 11 represents a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms.
  • R is a hydrogen atom or a lower alkyl group; X is a sulfur atom or an oxygen atom; n is an integer of 1 to 3; R 12 is a straight chain of 1 to (21-2n) carbon atoms] , Branched or cyclic alkyl groups. ]
  • one type may be used alone, or two or more types may be used in combination.
  • the proportion of the structural unit (al) in the polymer compound (A1) is preferably 5 mol% or more, more preferably 10 to 80 mol%, based on all the structural units constituting the polymer compound (A1). 20 to 70 mol% is more preferred, 10 to 50 mol% is particularly preferred, and 10 to 35 mol% is most preferred. By setting it to the lower limit value or more, the effect of the present invention is sufficient.
  • the polymer compound (Al) may have the above structural unit (al), for example, may be alkali-soluble, or may be one that increases alkali solubility by the action of an acid.
  • the resist composition containing the high molecular compound (A1) is negative when the high molecular compound (A1) is alkali-soluble, and the high molecular compound (A1) has increased alkali solubility due to the action of acid. When it is a thing, it becomes a positive type.
  • the polymer compound (A1) is preferably a compound (positive type) whose alkali solubility is increased by the action of an acid.
  • the high molecular compound (A1) When the high molecular compound (A1) has increased alkali solubility due to the action of an acid, the high molecular compound (A1) has an acid dissociable, dissolution inhibiting group (ex-lower alkyl) acrylic acid It is preferred to have a structural unit derived from Esterca ( a2 ).
  • the “lower alkyl) acrylate ester” means one or both of an acrylate ester and a lower alkyl acrylate ester such as a methacrylic acid ester.
  • the lower alkyl group as a substituent at the ⁇ -position of “( ⁇ -lower alkyl) acrylic acid ester” is an alkyl group having 1 to 5 carbon atoms, specifically, a methyl group or an ethyl group.
  • (a-lower alkyl) acrylic ester force-derived structural unit means a structural unit formed by cleavage of the ethylenic double bond of (a-lower alkyl) acrylic ester.
  • the acid dissociable, dissolution inhibiting group in the structural unit (a2) is an alkali-soluble compound that makes the entire polymer compound (A1) insoluble in alkali before exposure when the polymer compound (A1) is used as a resist composition. It can be used without particular limitation as long as it has anti-degradability and is dissociated by the action of an acid generated from the component (B) after exposure to change the entire polymer compound (A1) to alkali-soluble. it can.
  • a carboxyl group of (meth) acrylic acid and a group forming a cyclic or chain tertiary alkyl ester, a tertiary alkoxy carbo yl group, or a chain alkoxyalkyl group are widely known.
  • (meth) acrylic acid “Ester” means one or both of an acrylic ester and a methacrylic ester.
  • an acid dissociable, dissolution inhibiting group containing an aliphatic cyclic group can be preferably used.
  • aliphatic in the present invention is a relative concept with respect to aromatics, and is defined to mean groups, compounds, etc. that do not have aromaticity.
  • aliphatic cyclic group means that it has no aromaticity !, a monocyclic group or a polycyclic group (alicyclic group). In this case, the “aliphatic cyclic group” It is not limited to a group consisting of carbon and hydrogen (hydrocarbon group)
  • hydrocarbon group It is preferably a 1S hydrocarbon group.
  • the “hydrocarbon group” may be either saturated or unsaturated, but is usually preferably saturated.
  • a polycyclic group (alicyclic group) is preferred.
  • Such an aliphatic cyclic group include, for example, a monocycloalkane, bicycloalkane, tricycloalkane, which may or may not be substituted with a fluorine atom or a fluorinated alkyl group, Examples include groups in which one hydrogen atom has been removed from a teracycloalkane. Specific examples include monocycloalkanes such as cyclopentane and cyclohexane, and groups obtained by removing one hydrogen atom from polycycloalkanes such as adamantane, norbornane, isobornane, tricyclodecane, and tetracyclododecane.
  • Such monocyclic or polycyclic groups can be used by appropriately selecting the intermediate forces proposed in large numbers in ArF resists.
  • a cyclopentyl group, a cyclohexyl group, an adamantyl group, a norbornyl group, and a tetracyclododecanyl group are preferable from an industrial viewpoint, and an adamantyl group is particularly preferable.
  • structural unit (a2) include structural units represented by the following general formulas (a2-1) to (a2-9).
  • R is a hydrogen atom or an ⁇ -lower alkyl group, and R 1 is a lower alkyl group.
  • R is a hydrogen atom or a-lower alkyl group, and R 2 and R 3 are each independently a lower alkyl group.
  • R is a hydrogen atom or an ⁇ -lower alkyl group, and R 4 is a tertiary alkyl group.
  • R is a hydrogen atom or an ⁇ -lower alkyl group.
  • R is a hydrogen atom or an ⁇ -lower alkyl group, and R a is a methyl group.
  • R is a hydrogen atom or an ⁇ -lower alkyl group, and R 6 is a lower alkyl group.
  • R is a hydrogen atom or an ⁇ -lower alkyl group.
  • R is a hydrogen atom or an ⁇ -lower alkyl group.
  • the lower alkyl group for R is the lower alkyl group for R in the structural unit (al). Is the same.
  • Each of the ⁇ and R 6 to R 7, lower linear or branched alkyl group preferably tool methyl group of 1 to 5 carbon atoms, Echiru group, a propyl group, an isopropyl radical, n-butyl group, isobutyl group, tert Examples thereof include a butyl group, a pentyl group, an isopentyl group, and a neopentyl group. Industrially, a methyl group or an ethyl group is preferred.
  • R 4 is a tertiary alkyl group such as tert butyl group or tert-amyl group, and ter t butyl group is preferred industrially!
  • structural unit (a2) among the structural units listed above, structural units represented by general formulas (a2-1), (a2-2), (a2-3), and (a2-6) It is preferable because a pattern having excellent force resolution can be formed.
  • one type may be used alone, or two or more types may be used in combination.
  • the polymer compound (A1) is a lower alkyl containing a ratatone-containing monocyclic or polycyclic group. It is preferred to have a structural unit derived from ( a 3).
  • the lathetone-containing monocyclic or polycyclic group of the structural unit (a3) is used to increase the adhesion of the resist film to the substrate or to the developer when the polymer compound (A1) is used to form a resist film. It is effective in increasing the affinity for water.
  • the rataton here means one ring containing the -o-c (o)-structure, and this is counted as the ring of one eye. Therefore, in the case of only a rataton ring, 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 particular limitation as long as it has both such a structure of laton (10—C (O) —) and a cyclic group.
  • the containing monocyclic group include groups in which ⁇ ⁇ -petit-lataton force hydrogen atom is removed
  • examples of the rataton-containing polycyclic group include bicycloalkanes, tricycloalkanes, and tetracycloalkanes having a rataton ring.
  • the force can be a group with one hydrogen atom removed.
  • a group obtained by removing one hydrogen atom from a latatatone-containing tricycloalkane having the following structural formula (IV) or structural formula (V) is advantageous in terms of industrial availability. is there.
  • Examples of the structural unit (a3) include structural units derived from acrylate esters containing a latathone-containing monocycloalkyl group or a tricycloalkyl group ( ⁇ -lower alkyl group).
  • examples of the structural unit (a3) include structural units represented by general formulas (a3-l) to (a3-5) shown below.
  • R ′ is a hydrogen atom or a lower alkyl group.
  • R ′ is a hydrogen atom or a lower alkyl group.
  • This structural unit exists as a mixture of isomers at the 5- or 6-position.
  • R is a hydrogen atom or a lower alkyl group
  • R 8 and R 9 are each independently a hydrogen atom or a lower alkyl group.
  • R ′ is a hydrogen atom or a lower alkyl group, and o is 0 or 1.
  • R ′ is a hydrogen atom or a lower alkyl group
  • the lower alkyl group for R ′ is the above structural unit.
  • R 8 and R 9 are each independently a hydrogen atom or a lower alkyl group having 1 to 5 carbon atoms, and in view of industrial availability and the like, a hydrogen atom Is preferred.
  • the structural unit to be used is preferable because the shape of the resist pattern obtained when used in the resist composition, for example, the rectangularity is even better.
  • the structural unit represented by the general formula (a3-2) is preferable because its effect is extremely high. Of these, the structural unit represented by the general formula (a3-3) is most preferred.
  • the polymer compound (A1) as the structural unit (a3), only one type may be used, or two or more types different from each other may be used in combination.
  • the base of the resist film can be obtained. This is preferable because adhesion to the plate, affinity with an alkali developer, and etching resistance are further improved.
  • the polymer compound (A1) is not limited to the structural unit (al), in addition to the structural units (al) and (a2), or within the structural unit (al) as long as the effects of the present invention are not impaired.
  • (a4) may further have a structural unit (a4) derived from (a lower alkyl) acrylate ester force containing a polar group-containing aliphatic hydrocarbon group.
  • Examples of the polar group include a hydroxyl group and a cyan group, and a hydroxyl group is particularly preferable.
  • Examples of the aliphatic hydrocarbon group include a linear or branched hydrocarbon group (alkylene group) having 1 to 10 carbon atoms and a polycyclic aliphatic hydrocarbon group (polycyclic group).
  • alkylene group alkylene group
  • polycyclic group polycyclic group
  • a structural unit that contains a hydroxyl group, a cyano group, or a carboxyl group-containing aliphatic polycyclic group and that also induces (meth) acrylic acid ester power 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.
  • Such polycyclic groups can be appropriately selected and used for the polymers (resin components) for resist compositions for ArF excimer lasers that have been proposed in large numbers.
  • an adamantyl group, a norbornyl group, and a tetracyclododecanyl group are industrially preferable.
  • the structural unit (a4) when the hydrocarbon group in the polar group-containing aliphatic hydrocarbon group is a linear or branched hydrocarbon group having 1 to 10 carbon atoms, lower alkyl)
  • the structural unit derived from the hydroxyethyl ester power of lauric acid is preferred, and when the hydrocarbon group is a polycyclic group, structural units represented by the following formulas (a4-1) and (a4-2) are preferred. It is mentioned as a thing.
  • R ′ is the same as above, and n is an integer of 1 to 3.
  • n 1, and a force in which the hydroxyl group is bonded to the 3-position of the adamantyl group S is preferable.
  • R ′ is the same as defined above, and k is an integer of 1 to 3.
  • the structural unit (a4) is a polymer compound (A1) This is a polymer compound When contained in the product (Al), 5 mol% or less is preferable with respect to the total of all the structural units constituting the polymer compound (A1), and 3 mol% or less is more preferable (a4 ) Is most preferred. If the upper limit is exceeded, the effects of the present invention may be impaired. In addition, the resist pattern shape may deteriorate due to the balance of other structural units.
  • the polymer compound (Al) is not classified as the structural unit (al), or (a4), as long as the effects of the present invention are not impaired. It may have other structural unit (a5).
  • the structural unit (a5) for example, a structural unit containing an acid non-dissociable aliphatic polycyclic group and derived from an ( ⁇ -lower alkyl) acrylate ester is preferable.
  • the isolation pattern power is also semi-densitive (the line and space pattern with a space width of 1.2 to 2 with respect to a line width of 1). Excellent and preferred.
  • Examples of the polycyclic group include those similar to those exemplified in the case of the structural unit (a4), and are conventionally known as ArF positive resist materials! Many powers can be selected and used as appropriate.
  • At least one kind selected from tricyclodecanyl group, adamantyl group, tetracyclododecyl group, isobornyl group and norbornyl group is preferable in terms of industrial availability.
  • the powerful structural unit (a5) is not an essential component of the polymer compound (A1), but when it is contained in the polymer compound (A1), it constitutes the polymer compound (A1).
  • the structural unit (a5) is contained in an amount of 1 to 30 mol%, preferably 10 to 20 mol%, based on the total of all the structural units, a good improvement effect can be obtained in the resolution of the isolated pattern power and the semi-dense pattern. Therefore, it is preferable.
  • the polymer compound (A1) is obtained by copolymerizing monomers corresponding to the respective structural units by a known radical polymerization using a radical polymerization initiator such as azobisisobutyl-tolyl (AIBN). Can be manufactured easily.
  • a radical polymerization initiator such as azobisisobutyl-tolyl (AIBN).
  • the mass average molecular weight of the polymer compound (A1) (polystyrene equivalent, the same shall apply hereinafter) is particularly limited, and it is preferred that the repulsive force is 3000 to 50000 force ⁇ , 5000 to 20000 force. 5000-15000 force is more preferred. Within this range, solubility in a resist solvent, dry etching resistance, and resist pattern cross-sectional shape are improved.
  • the degree of dispersion of the polymer compound (A1) is 1.0 to 5.0, more preferably 1.0 to 3.5.
  • the resist composition of the present invention comprises a rosin component (alkaline solubility that changes due to the action of an acid)
  • the component (ii) is the polymer compound of the present invention.
  • the resist composition of the present invention may be positive or negative as long as it has the above characteristics.
  • a positive type is preferred.
  • a crosslinking agent is blended in the resist composition together with the alkali-soluble resin and the component (ii).
  • a strong acid acts to cause cross-linking between the alkali-soluble resin and the cross-linking agent, thereby changing to alkali-insoluble.
  • crosslinking agent for example, an amino-based crosslinking agent such as glycoluril having a methylol group or an alkoxymethyl group, particularly a butoxymethyl group, a melamine-based crosslinking agent, It is preferable to use a urea-based cross-linking agent or an ethylene urea-based cross-linking agent because a good resist pattern can be formed.
  • the amount of the crosslinking agent is preferably in the range of 1 to 50 parts by mass with respect to 100 parts by mass of the alkali-soluble resin.
  • the component (A) is an alkali-insoluble one having a so-called acid dissociable, dissolution inhibiting group, and when an acid is generated from the component (B) by exposure, a strong acid is converted into the acid. By dissociating the dissociable, dissolution inhibiting group, the component (A) becomes alkali-soluble.
  • the component (A) is the polymer compound (A1) of the present invention.
  • the polymer compound (A1) in addition to the polymer compound (A1), other resin components that can be used in the resist composition, such as a known polyhydroxystyrene resin and (meth) acrylic resin, are appropriately combined.
  • the proportion of the polymer compound (A1) in the resin composition contained in the resist composition is 80% by mass or more. More preferably, it is 100% by mass or more.
  • the proportion of the component (A) in the resist composition can be appropriately adjusted depending on the intended resist film thickness.
  • the component (B) can be used without particular limitation from known acid generators used in conventional chemically amplified resist compositions.
  • acid generators examples include onium salt-based acid generators such as iodine salts and sulfo-um salts, oxime sulfonate-based acid generators, bisalkyl or bis-aryl sulfo-diazomethanes, There are various known diazomethane acid generators such as poly (bissulfol) diazomethanes, nitrobenzil sulfonate acid generators, iminosulfonate acid generators, disulfone acid generators, and the like.
  • onium salt-based acid generators such as iodine salts and sulfo-um salts, oxime sulfonate-based acid generators, bisalkyl or bis-aryl sulfo-diazomethanes
  • diazomethane acid generators such as poly (bissulfol) diazomethanes, nitrobenzil sulfonate acid generators, iminosulfonate acid generator
  • acid salt-based acid generators include trifluoromethane sulfonate or nonafluorobutane sulfonate of bisphenol 4-bis- (4-tert-butylphenol).
  • oxime sulfonate-based acid generators include ⁇ - (P-toluenesulfo-luoximino) -benzyl cyanide, a- (p-chlorobenzenebenzene-sulfoximino) -benzil cyanide, a- ( 4-Nitrobenzenesulfo-luoximino) -benzyl cyanide, a- (4-Nitro-2-trifluoromethylbenzenesulfo-luoximino) -benzyl cyanide, a- (benzenesulfo-roximino) -4-black mouth Benzyl cyanide, a-(Benzenesulfo-luximinomino)-2, 4-dichlorobenzil cyanide, a-(Benzenesulfo-roximinomino) -2, 6-dichlorobenzil cyanide, a-(Benzenesulfo- (
  • bisalkyl or bisarylsulfol-diazomethanes include bis (isopropylsulfol) diazomethane, bis ( ⁇ toluenesulfol) diazomethane, and bis (1,1- Dimethylethylsulfol) diazomethane, bis (cyclohexylsulfol) diazomethane, bis (2,4 dimethylphenolsulfol) ) Diazomethane and the like.
  • poly (bissulfonyl) diazomethanes have the following structure:
  • an onium salt having a fluorinated alkyl sulfonate ion as an ion as the component (B).
  • one type of acid generator may be used alone, or two or more types may be used in combination.
  • the content of the component (B) is 0.5 to 30 parts by mass, preferably 1 to 10 parts by mass with respect to 100 parts by mass of the component (A). If it is less than the above range, pattern formation may not be performed sufficiently. If the above range is exceeded, it may be difficult to obtain a uniform solution, which may cause a decrease in storage stability.
  • the resist composition of the present invention can be produced by dissolving the component (A), the component (B) and any components described later in an organic solvent (hereinafter sometimes referred to as the component (C)).
  • any component can be used as long as it can dissolve each component to be used to form a uniform solution. Two or more kinds can be appropriately selected and used.
  • ketones such as ⁇ -butyrolatatone, acetone, methyl ethyl ketone, cyclohexanone, methyl isoamyl ketone, 2-heptanone, ethylene glycol, ethylene glycol monoacetate, diethylene glycol, diethylene glycol monoacetate, propylene Polyols and their derivatives such as glycol, propylene glycolol monoacetate, dipropylene glycol, or monomethyl ether, monoethyl ether, monopropyl ether, monobutyl ether or monophenyl ether of dipropylene glycol monoacetate, and dioxane Cyclic ethers, methyl lactate, ethyl lactate (EL), methyl acetate, ethyl acetate, butyl acetate, methyl pyruvate, ethyl pyruvate, Methyl Tokishipuropion acid, and ethoxy propionic acid Echiru
  • organic solvents can 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 (mass ratio) may be appropriately determined in consideration of the compatibility between PGMEA and the polar solvent, but is preferably 9: 1 to 1: 9, more preferably 8: 2 to 2: 8. Preferably within range! /.
  • the mass ratio of PGMEA: EL is preferably 8: 2 to 2: 8, more preferably 7: 3 to 3: 7! / ,.
  • component (C) a mixed solvent of at least one selected from among PGMEA and EL and ⁇ -petit-mouth rataton is also preferable.
  • the mixing ratio of the former and the latter is preferably 70: 30-95: 5.
  • component (C) propylene glycol monomethyl ether (PGME) is also preferable.
  • the amount of component (C) used is not particularly limited, and is a concentration that can be applied to a support such as a substrate, and is appropriately set according to the coating film thickness. It is used so that the solid content concentration is in the range of 220 mass%, preferably 5 15 mass%.
  • the resist composition of the present invention may further include any desired resist pattern shape, post ex posure stability of the latent image rormed by the pattern-wise exposure of the resist layer, etc.
  • a nitrogen-containing organic compound (D) hereinafter referred to as “component (D)” can be blended.
  • 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).
  • an organic carboxylic acid or phosphorous is further added as an optional component.
  • an derivative thereof (E) hereinafter referred to as “component (E)”.
  • the component (D) and the component (E) can be used in combination, or any one of them can be used.
  • organic carboxylic acid for example, malonic acid, citrate, malic acid, succinic acid, benzoic acid, salicylic acid and the like are suitable.
  • Phosphorus oxoacids or derivatives thereof include phosphoric acid, phosphoric acid di-n-butyl ester, phosphoric acid diphenol ester and other derivatives such as phosphoric acid, phosphonic acid, phosphonic acid dimethyl ester, Phosphonic acids such as phosphonic acid-di-n-butyl ester, phenylphosphonic acid, phosphonic acid diphenyl ester, phosphonic acid dibenzyl ester and derivatives thereof, phosphines such as phosphinic acid, phenylphosphinic acid, etc. Derivatives such as acids and their esters are mentioned, among which phosphonic acid is particularly preferred.
  • Component (E) is used in a proportion of 0.01 to 5.0 parts by mass per 100 parts by mass of component (A).
  • the resist composition of the present invention may further contain miscible additives such as an additional resin for improving the performance of the resist film, a surfactant for improving the coating property, and a dissolution inhibitor.
  • miscible additives such as an additional resin for improving the performance of the resist film, a surfactant for improving the coating property, and a dissolution inhibitor.
  • plasticizers, stabilizers, colorants, antihalation agents, and the like can be added and contained as appropriate.
  • the resist pattern forming method of the present invention includes a step of forming a resist film on a substrate using the resist composition of the present invention, a step of exposing the resist film, and forming a resist pattern by imaging the resist film. Process.
  • the resist composition of the present invention is applied onto a substrate such as a silicon wafer with a spinner or the like, and then pre-beta is performed.
  • the resist composition coating film is selectively exposed through a desired mask pattern, and then subjected to PEB (post-exposure heating).
  • PEB post-exposure heating
  • the developer on the substrate and the resist composition dissolved by the developer are washed, poured and dried.
  • the operating conditions are preferably set as appropriate according to the composition and characteristics of the resist composition to be used.
  • the light source used in the exposure process is not limited, but far ultraviolet light with a wavelength of 300 nm or less, specifically KrF excimer laser, ArF excimer laser, F excimer
  • the resist composition useful in the present invention is particularly effective for ArF excimer laser.
  • a post-beta step after the alkali development may be included, and an organic or inorganic antireflection film may be provided between the substrate and the coating layer of the resist composition.
  • the heating temperature in the pre-beta and the heating temperature in the post-exposure heating (PEB) may generally be 90 ° C or more, but in order to form a resist pattern with good rectangularity, it is particularly 90-140 respectively. ° C, preferably 90-130 ° C is preferred. In addition, by using this temperature range, the generation of microbridges can be effectively suppressed.
  • a polymer compound that can constitute a high-resolution resist composition, a compound suitable for producing the polymer compound, and the polymer compound are contained.
  • a resist composition and a resist pattern forming method using the resist composition are obtained.
  • the contact angle with water can be increased by using a resist composition containing the polymer compound of the present invention.
  • the contact angle of the resist film with a rinse solution such as water is high (difficult to adjust to water) in the pure water rinsing process performed in the resist pattern forming process.
  • the problem of pattern collapse that has been a problem can be improved.
  • the compound (a) since the compound (a) has a nitrogen atom, Therefore, it is expected that the diffusion of the acid generated from the component (B) in the resist film is suppressed, and accordingly, the resolution and the roughness of the pattern side wall are also expected to be improved.
  • the compound (a) of the present invention has a nitrogen atom, it can be used as the component (D) defined in the present specification.
  • a resist composition having a function of the component (D) in the resin skeleton can be provided. it can. Unlike a normal resist composition, the resist composition has a component (D) in the resin skeleton, so that it is expected that elution into water is suppressed, and immersion lithography is performed. It can also be suitably used as a resist composition.
  • Table 1 below shows the types of monomers used for synthesizing resins 1 to 5, the composition ratio (molar ratio) of each structural unit that also induces the monomer power, and the molecular weight and dispersity of resins 1 to 5. Indicates.
  • Component (A) Resin 2 100 parts by mass
  • Component (D) Triethanolamine 0.15 parts by mass
  • An organic antireflective coating composition “ARC-29A” (trade name, manufactured by Brew Science Co., Ltd.) was applied onto an 8-inch silicon wafer using a spinner and baked on a hot plate at 215 ° C. for 60 seconds. Then, an organic antireflection film having a thickness of 77 nm was formed by drying, and the resist composition obtained above was applied onto the antireflection film using a spinner, and 100 ° on a hot plate. C, pre-beta (PAB) for 90 seconds, and dried to form a resist film with a thickness of 200 nm.
  • PAB pre-beta
  • ArF excimer laser (193nm) is selected via mask pattern (binary mask) Irradiated.
  • a PEB treatment was conducted under conditions of 100 ° C, 90 seconds, further 23 ° C at 2.38 mass 0/0 tetra Mechiruanmo - Umuhidorokishido (TMAH) puddle developed for 60 seconds with an aqueous solution, washed with water dried then 20 seconds did.
  • TMAH Mechiruanmo - Umuhidorokishido
  • the contact angle was measured using a FACE contact angle meter CA-X150 (product name, manufactured by Kyowa Interface Science Co., Ltd.).
  • the mask (L & S, 1: 1) size is changed from lOOnm to 200 nm, a resist pattern is formed in the same manner as described above, and the size of the resist pattern to be formed is changed. It was measured.
  • FIG. 1 shows the results of Example 11 and Comparative Example 1.
  • Example 11 a resist pattern more faithful to the mask was formed than in Comparative Example 1.
  • the horizontal axis is the mask size (space width, nm)
  • the vertical axis is the resist pattern size (CD) (line width, nm)
  • the two broken lines are lines where the resist pattern size is 5% of the mask size. The closer to the straight line A, the better the mask reproducibility.
  • a positive resist composition was prepared in the same manner as in Example 1, except that PAB and PEB were each changed to 130 ° C. for 90 seconds, and evaluated in the same manner as in Example 1.
  • LZS line and space
  • the contact angle with water increased in the resist composition of Example 11 as compared to the resist composition of Comparative Example 1.
  • the resist pattern obtained using the resist composition had excellent resolution.
  • the resist composition of Example 11 had better mask reality than the resist composition of Comparative Example 1.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Physics & Mathematics (AREA)
  • Materials For Photolithography (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L’invention concerne un composé représenté par la formule générale (1) ci-dessous. (1) [Dans la formule, R représente un atome d’hydrogène ou un groupe alkyle inférieur ; X représente un atome de soufre ou un atome d’oxygène ; Y représente un groupe alkyle cyclique, ramifié ou à chaîne qui comprend de 1 à 20 atomes de carbone où une partie des atomes d’hydrogène peuvent être substitués par un groupe contenant un hétéroatome ou un groupe alkyle où une partie des atomes de carbone sont substitués par un hétéroatome.]
PCT/JP2005/013473 2004-07-30 2005-07-22 Nouveau composé, composé de polymère, composition de résist et procédé pour former un motif de résist Ceased WO2006011420A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2004224364 2004-07-30
JP2004-224364 2004-07-30
JP2005-184673 2005-06-24
JP2005184673A JP5008838B2 (ja) 2004-07-30 2005-06-24 高分子化合物、レジスト組成物およびレジストパターン形成方法

Publications (1)

Publication Number Publication Date
WO2006011420A1 true WO2006011420A1 (fr) 2006-02-02

Family

ID=35786169

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2005/013473 Ceased WO2006011420A1 (fr) 2004-07-30 2005-07-22 Nouveau composé, composé de polymère, composition de résist et procédé pour former un motif de résist

Country Status (3)

Country Link
JP (1) JP5008838B2 (fr)
TW (1) TWI347312B (fr)
WO (1) WO2006011420A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130157201A1 (en) * 2011-11-25 2013-06-20 Tokyo Ohka Kogyo Co., Ltd. Resist composition, method of forming resist pattern, and polymeric compound
US20140287361A1 (en) * 2013-03-25 2014-09-25 Tokyo Ohka Kogyo Co., Ltd. Resist composition and resist pattern forming method
US9057948B2 (en) 2011-10-17 2015-06-16 Tokyo Ohka Kogyo Co., Ltd. Resist composition for EUV or EB, and method of forming resist pattern
US9274424B2 (en) 2013-03-25 2016-03-01 Tokyo Ohka Kogyo Co., Ltd. Resist composition and resist pattern forming method

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4355011B2 (ja) 2006-11-07 2009-10-28 丸善石油化学株式会社 液浸リソグラフィー用共重合体及び組成物
TWI462938B (zh) * 2008-05-21 2014-12-01 Sumitomo Chemical Co 聚合物及含有該聚合物之化學放大型阻劑組成物
EP2393106A4 (fr) * 2009-01-29 2012-10-03 Showa Denko Kk Composition durcissable pour matériau de transfert et composé d'urée contenant un groupe (méth)acryloyle
JP5856441B2 (ja) 2011-11-09 2016-02-09 東京応化工業株式会社 レジスト組成物、レジストパターン形成方法及び高分子化合物
JP6018812B2 (ja) * 2012-06-19 2016-11-02 東京応化工業株式会社 レジスト組成物、レジストパターン形成方法、化合物、化合物の製造方法、高分子化合物
JP6093614B2 (ja) 2013-03-25 2017-03-08 東京応化工業株式会社 レジスト組成物及びレジストパターン形成方法
JP6343467B2 (ja) * 2013-03-27 2018-06-13 東京応化工業株式会社 レジスト組成物、及びレジストパターン形成方法
JP6435109B2 (ja) 2013-04-26 2018-12-05 東京応化工業株式会社 レジスト組成物、レジストパターン形成方法
US10324377B2 (en) * 2015-06-15 2019-06-18 Tokyo Ohka Kogyo Co., Ltd. Resist composition and method of forming resist pattern
JP6170990B2 (ja) * 2015-12-10 2017-07-26 東京応化工業株式会社 化合物

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61272208A (ja) * 1985-05-28 1986-12-02 Nippon Paint Co Ltd 含フツ素ポリマ−およびその製法
JPS6346203A (ja) * 1986-04-22 1988-02-27 Nippon Paint Co Ltd 水分散性樹脂
JPH10175938A (ja) * 1996-12-18 1998-06-30 Canon Inc 有機化合物、その重合体および有機電界発光素子
JPH10316643A (ja) * 1997-05-19 1998-12-02 Showa Denko Kk 重合性マロン酸誘導体および硬化性組成物
JPH11255831A (ja) * 1998-03-13 1999-09-21 Agency Of Ind Science & Technol 複合刺激応答性高分子誘導体
WO2002016454A1 (fr) * 2000-08-21 2002-02-28 National Institute Of Advanced Industrial Science And Technology Polymeres

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0140273B1 (fr) * 1983-11-01 1991-09-11 Hoechst Celanese Corporation Composition pour photoréserve sensible dans l'UV profond, élément photosensible et image photochimique résistante à la chaleur le contenant

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS61272208A (ja) * 1985-05-28 1986-12-02 Nippon Paint Co Ltd 含フツ素ポリマ−およびその製法
JPS6346203A (ja) * 1986-04-22 1988-02-27 Nippon Paint Co Ltd 水分散性樹脂
JPH10175938A (ja) * 1996-12-18 1998-06-30 Canon Inc 有機化合物、その重合体および有機電界発光素子
JPH10316643A (ja) * 1997-05-19 1998-12-02 Showa Denko Kk 重合性マロン酸誘導体および硬化性組成物
JPH11255831A (ja) * 1998-03-13 1999-09-21 Agency Of Ind Science & Technol 複合刺激応答性高分子誘導体
WO2002016454A1 (fr) * 2000-08-21 2002-02-28 National Institute Of Advanced Industrial Science And Technology Polymeres

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9057948B2 (en) 2011-10-17 2015-06-16 Tokyo Ohka Kogyo Co., Ltd. Resist composition for EUV or EB, and method of forming resist pattern
US20130157201A1 (en) * 2011-11-25 2013-06-20 Tokyo Ohka Kogyo Co., Ltd. Resist composition, method of forming resist pattern, and polymeric compound
US8778595B2 (en) * 2011-11-25 2014-07-15 Tokyo Ohka Kogyo Co., Ltd. Resist composition, method of forming resist pattern, and polymeric compound
TWI572625B (zh) * 2011-11-25 2017-03-01 東京應化工業股份有限公司 光阻組成物，光阻圖型之形成方法及高分子化合物
US20140287361A1 (en) * 2013-03-25 2014-09-25 Tokyo Ohka Kogyo Co., Ltd. Resist composition and resist pattern forming method
US9235123B2 (en) * 2013-03-25 2016-01-12 Tokyo Ohka Kogyo Co., Ltd. Resist composition and resist pattern forming method
US9274424B2 (en) 2013-03-25 2016-03-01 Tokyo Ohka Kogyo Co., Ltd. Resist composition and resist pattern forming method

Also Published As

Publication number Publication date
TWI347312B (en) 2011-08-21
TW200611886A (en) 2006-04-16
JP5008838B2 (ja) 2012-08-22
JP2006063318A (ja) 2006-03-09

Similar Documents

Publication Publication Date Title
JP4794835B2 (ja) 高分子化合物、酸発生剤、ポジ型レジスト組成物、およびレジストパターン形成方法
WO2007138893A1 (fr) Composition de résist positif et procédé de formation d'un motif de résist
WO2006011420A1 (fr) Nouveau composé, composé de polymère, composition de résist et procédé pour former un motif de résist
JP4828204B2 (ja) ポジ型レジスト組成物およびレジストパターン形成方法、並びに高分子化合物
JP4213107B2 (ja) レジスト組成物およびレジストパターン形成方法
WO2008068971A1 (fr) Composition de résist positif pour une exposition à une immersion dans un liquide et procédé de formation de motif de résist
WO2008013030A1 (fr) Composé, générateur d'acide, composition de réserve et procédé pour former un motif de réserve
WO2006082740A1 (fr) Composition de résist à fonctionnement positif et procédé de formation de motif de résist
WO2007148492A1 (fr) Composition de résine positive et procédé de formation d'un motif de résine
WO2007148525A1 (fr) Composition de réserve positive et procédé de formation d'un motif de réserve
WO2006123496A1 (fr) Composition de reserve positive et procede pour la formation d'un dessin de reserve
WO2006064622A1 (fr) Composition de resistpositif et procede de formation d’un motif de resist
JP2006058842A (ja) レジスト組成物およびレジストパターン形成方法
JP4791184B2 (ja) レジスト用樹脂、ポジ型レジスト組成物及びレジストパターン形成方法
JP4841823B2 (ja) 高分子化合物、ポジ型レジスト組成物およびレジストパターン形成方法
WO2008007578A1 (fr) Composé, générateur d'acide, composition de résist et procédé de formation d'un motif de résist
US8097396B2 (en) Positive resist composition and method for forming resist pattern
JP2006003781A (ja) ポジ型レジスト組成物及びレジストパターン形成方法
WO2006080151A1 (fr) Procédé de formation d’un motif de réserve
WO2006087865A1 (fr) Composition de resine positive et procede pour former un modele de resine
WO2007102425A1 (fr) Composition de réserve positive et procédé de formation de motif de réserve
JP4684740B2 (ja) ポジ型レジスト組成物およびレジストパターン形成方法
JP2005010488A (ja) ポジ型レジスト組成物
WO2006115017A1 (fr) Composition de résist positif et procédé de formation d'un motif de résist
JP5576411B2 (ja) 新規な化合物

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS KE KG KM KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NG NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SM SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LT LU LV MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase