WO2008032736A1 - Composition de résist contenant un colorant contenant un générateur de photoacide, et composé de sulfonate d'oxime de type cyclohexadiène - Google Patents

Composition de résist contenant un colorant contenant un générateur de photoacide, et composé de sulfonate d'oxime de type cyclohexadiène Download PDF

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Publication number
WO2008032736A1
WO2008032736A1 PCT/JP2007/067726 JP2007067726W WO2008032736A1 WO 2008032736 A1 WO2008032736 A1 WO 2008032736A1 JP 2007067726 W JP2007067726 W JP 2007067726W WO 2008032736 A1 WO2008032736 A1 WO 2008032736A1
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group
carbon atoms
dye
compound
resist composition
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PCT/JP2007/067726
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English (en)
Japanese (ja)
Inventor
Hideo Suzuki
Tomoe Miyazawa
Takamasa Kikuchi
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Nissan Chemical Industries, Ltd.
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Publication of WO2008032736A1 publication Critical patent/WO2008032736A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/63—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C255/64—Carboxylic acid nitriles containing cyano groups and nitrogen atoms further bound to other hetero atoms, other than oxygen atoms of nitro or nitroso groups, bound to the same carbon skeleton with the nitrogen atoms further bound to oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • 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
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments

Definitions

  • Dye-containing resist composition containing photoacid generator and cyclohexagen-based oxime sulfonate compound
  • the present invention relates to a dye-containing resist composition containing a photoacid generator and a cyclohexagen-based oxime sulfonate compound. More specifically, the present invention relates to a dye-containing composition containing a photoacid generator corresponding to i-line (365 nm). The present invention relates to a resist composition.
  • a color filter for an image sensor such as a charge coupled device (CCD) or a liquid crystal display device (LCD) is capable of producing a high-definition color filter mainly because a fine pattern can be formed. Therefore, it is produced using a method of forming a pattern with a photoresist added with a dye.
  • a resist composition containing a dye and a polymer resin is used. After coating the film on a substrate, the colored layer is patterned and developed by a photolithography method to form a single colored pattern. Then, this process is repeated for each color to produce a color filter.
  • pigments that are excellent in heat resistance and light stability are generally used as the coloring agent used as the colorant, and resists in which pigments are dispersed have been proposed.
  • a photosensitive colored resin composition comprising a resin material that can be hardened by an acid, a photoacid generator, and a pigment (for example, Patent Document 1). It is disclosed that the resin material consists of a resin containing phenol and a crosslinking agent having an N-methylol structure.
  • the pigment itself contains particles having a particle size of several tens of nm! / And several hundreds of nm, the pigment itself becomes a foreign substance, or the dispersion is not stable and causes aggregation. There was a problem. For this reason, using conventional pigments makes it difficult to produce color filters for CCDs that require high resolution.
  • a uniform resist composition can be obtained because the dye is soluble in an organic solvent. Therefore, a resist composition in which pigments are dispersed It is possible to form a fine pattern as compared with an object.
  • a negative resist composition comprising a resin curable with an acid, a crosslinking agent, a photoacid generator, a dye and a solvent is disclosed (for example, Patent Document 2).
  • a resist-added dye for a color filter that is an amine salt of an acid dye and is soluble in an organic solvent and an alkaline aqueous solution is disclosed (for example, Patent Document 3).
  • an ink composition containing a reaction mixture of a water-soluble dye having active hydrogen, an epoxy compound, and an amine as a colorant. It is described that these are used for writing instruments, printing, recording, stamping, and paper coloring (for example, Patent Document 5).
  • a photoacid generator! / An oxime sulfonate compound that has an excellent absorption coefficient (photosensitivity) for g-line, h-line and i-line, and excellent solubility in solvents. It is known (for example, Patent Document 6).
  • Patent Document 1 Japanese Patent Laid-Open No. 4 163552
  • Patent Document 2 Japanese Patent Laid-Open No. 6-51514
  • Patent Document 3 JP-A-6-51115
  • Patent Document 4 JP-A-60-229953
  • Patent Document 5 Japanese Patent Laid-Open No. 61-203182
  • Patent Document 6 Special Table 2002-508774
  • Patent Document 7 International Publication No. 2006/046398 Pamphlet
  • a dye-containing resist composition using a thiophene oxime sulfonate compound as a photoacid generator is colored by exposure and subsequent heat treatment. Have it!
  • the present invention has been made in view of such circumstances, and an object thereof is to provide a dye-containing resist composition that provides a color filter in which coloring in the visible region (400 nm to 730 nm) is suppressed.
  • Another object of the present invention is to provide a photoacid generator that is excellent in sensitivity to active light used for exposure, in particular, sensitivity to i-line (365 nm), has little coloration by exposure and subsequent heat treatment, and can produce a resist. To do.
  • the present inventors have found that a dye-containing resist composition containing a cyclohexagen-based oxime sulfonate compound as a photoacid generator.
  • the maximum absorption wavelength of the compound having a 2,6-substituted phenyl group almost coincides with the i-line wavelength of 365 nm.
  • the present inventors have completed the present invention by finding that a resist produced using the resist has high light transmittance and little coloring.
  • the present invention provides:
  • R 2 , R 5 , R 6 and R ′ are each independently a hydrogen atom, a halogen atom, CN, NO, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 5 carbon atoms. Represents a haloalkyl group having 1 to 5 carbon atoms or a haloalkoxy group having 1 to 5 carbon atoms,
  • R 3 represents a hydrogen atom, a halogen atom, a nitro group, a CN group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or the number of carbon atoms.
  • each R 3 may be the same as or different from each other, and when R 3 is adjacent
  • the two adjacent R 3 groups are — CH CH —CH O— — CH N (R 8 ) — — CH CH CH —CH CH O— CH CH N (R CH CH CH CH CH —CH CH CH O— —
  • CH CH CH N (R CH CH CH CH CH CH CH CH O— or one CH CH CH CH N (R 8 ) — By forming CH CH CH N (R CH CH CH CH CH CH CH CH CH CH CH CH CH O— or one CH CH CH N (R 8 ) —, a four-membered ring with the carbon atom to which each of the two R 3 bonds is attached.
  • 5-membered ring or 6-membered ring may be formed
  • R 4 is an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a haloalkoxy group having 1 to 5 carbon atoms,
  • R 8 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
  • W is a halogen atom, CN NO, an alkyl group having 1 to 10 carbon atoms, or the number of carbon atoms
  • alkoxy group having 1 to 5 carbon atoms a haloalkyl group having 1 to 5 carbon atoms, or a haloalkoxy group having 1 carbon atom and 5 haloalkoxy groups,
  • n an integer of 1 2 3 or 4.
  • a dye-containing resist composition comprising a photoacid generator comprising a cyclohexadiene oxime sulfonate compound represented by:
  • R 5 to R 7 are all hydrogen atoms, and R 1 and R 2 are each independently a halogen atom, CN NO, an alkyl group having 1 to 10 carbon atoms, or 1 carbon atom.
  • the dye (D) is represented by the formula [2]
  • the dye-containing resist composition according to 6 which comprises a cationic compound represented by:
  • a method for producing a color filter comprising the steps of: applying one dye-containing resist composition onto a substrate, drying, exposing and developing;
  • a liquid crystal display device including a color filter manufactured by 13 methods,
  • LED (light emitting diode) display device including color filters manufactured by 13 methods Place
  • a solid-state imaging device including a color filter manufactured by 13 methods
  • R 1 and R 2 are each independently a halogen atom, CN NO, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or Represents a haloalkyl group or a haloalkoxy group having 1 to 5 carbon atoms,
  • R 3 represents a hydrogen atom, a halogen atom, a nitro group, a CN group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or the number of carbon atoms.
  • each R 3 may be the same as or different from each other, and when R 3 is adjacent
  • the two adjacent R 3 groups are — CH CH —CH O— — CH N (R 8 ) — — CH CH CH —CH CH O— CH CH N (R CH CH CH CH CH —CH CH CH O— —
  • CH CH CH N (R CH CH CH CH CH CH CH CH O— or one CH CH CH CH N (R 8 ) — By forming CH CH CH N (R CH CH CH CH CH CH CH CH CH CH CH CH CH O— or one CH CH CH N (R 8 ) —, a four-membered ring with the carbon atom to which each of the two R 3 bonds is attached.
  • 5-membered ring or 6-membered ring may be formed
  • R 4 is an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a haloalkoxy group having 1 to 5 carbon atoms,
  • R 8 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
  • W is a halogen atom, CN NO, an alkyl group having 1 to 10 carbon atoms, or the number of carbon atoms An alkoxy group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or a haloalkoxy group having 1 carbon atom and 5 haloalkoxy groups,
  • n an integer of 1 2 3 or 4.
  • R 1 and R 2 are each independently a halogen atom, CN NO, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or Represents a haloalkyl group or a haloalkoxy group having 1 to 5 carbon atoms,
  • R 3 represents a hydrogen atom, a halogen atom, a nitro group, a CN group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or the number of carbon atoms.
  • each R 3 may be the same as or different from each other, and when R 3 is adjacent
  • the two adjacent R 3 groups are — CH CH —CH O— — CH N (R 8 ) — — CH CH CH —CH CH O— CH CH N (R CH CH CH CH CH —CH CH CH O— —
  • a 4-membered ring, a 5-membered ring or a 6-membered ring may be formed together with the carbon atom to which each R 3 is bonded.
  • R 8 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
  • n an integer of 1, 2, 3 or 4.
  • a photoacid generator comprising a cyclohexadiene oxime sulfonate compound represented by the formula [3],
  • An i-line photoacid generator comprising a cyclohexadiene oxime sulfonate compound represented by the formula [3]
  • the dye-containing resist composition of the present invention is less colored by exposure and subsequent heat treatment, thereby making it possible to improve the characteristics of the color filter.
  • a color filter having high heat resistance and light resistance can be produced by the interaction between the phenolic resin and the dye.
  • the dye-containing resist composition of the present invention can be thinned when a color filter is produced by increasing the dye concentration in the resist composition. In order to set the film thickness of the color filter from 0.3 to 1.5 111, the dye concentration in the resist composition must be 30% by mass or more.
  • the resist composition containing the dye molecule and the color filter produced from the resist composition have a region exhibiting a transmittance of 70% or more and a wavelength of 10% or less in the wavelength region of 400 to 700 nm due to the dye molecule.
  • the dye-containing resist composition of the present invention has a region showing a transmittance of 70% or more and a region showing a transmittance of 10% or less in the visible region (400 nm to 730 ⁇ m), particularly 400 to 700 nm. It contains at least a dye exhibiting a spectral spectrum.
  • Dyes such as red, green, and blue have specific areas where each dye absorbs (area where the transmittance is 10% or less) and areas where the dye does not absorb (area where the transmittance is 70% or more). It is preferable that the region does not show absorption, and that the region inhibits absorption of other dyes! When each dye has absorption in a region that does not inherently exhibit absorption, the heat resistance or light resistance of the dye is insufficient.
  • the dye used in the dye-containing resist composition of the present invention has a transmittance of 10% or less in a specific region showing absorption, and has a transmittance in a region showing no absorption.
  • the photoacid generator comprising the cyclohexadiene oxime sulfonate compound of the present invention exhibits high compatibility with the other main components of the resist composition, that is, the resin, the crosslinkable compound, the dye and the solvent.
  • the cyclohexagen-based oxime sulfonate compound having a 2,6-substituted phenyl group according to the present invention has a maximum absorption wavelength almost coincident with the i-line wavelength of 365 nm, and the resist produced using the compound is colored. Has a high light transmittance.
  • the dye-containing resist composition according to the present invention contains a photoacid generator composed of a cyclohexagen-based oxime sulfonate compound represented by the formula [1].
  • R 1 , R 2 , R 5 , R 6 and R 7 are each independently a hydrogen atom, a nitrogen atom, CN, NO, or an alkyl having 1 to 10 carbon atoms.
  • R 3 represents a hydrogen atom, a halogen atom, a nitro group, or a CN group
  • n is 2, 3 or 4 represents each R 3 may be the same or different from each other.
  • R 3 when R 3 is adjacent, two adjacent R 3 are CH 2 CH 2 --CH O CH N (R 8 )--CH CH CH CH CH O CH CH N (R 8 DOO, -CH CH CH CH -CH CH CH O CH CH CH N (RCH CH CH CH CH CH CH CH CH O or by forming a CH CH CH CH N (R 8 ), each of the two R 3 May form a 4-membered ring, a 5-membered ring or a 6-membered ring with the carbon atom to which R is bonded.
  • R 8 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, and n is 1 2 3 Or represents an integer of 4.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, an s-butyl group, an n-amyl group, an i-aminole group, s Amino group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group and the like.
  • alkoxy group having 1 to 5 carbon atoms include a methoxy group, an ethoxy group, an n propoxy group, an i propoxy group, an n -butoxy group, and an n amyloxy group.
  • a haloalkyl group having 1 to 5 carbon atoms Specific examples thereof include trifluoromethyl group, pentafluoroethyl group, perfluoro n propyl group, perfluoro n butyl group, perfluoro n amyl group and the like.
  • haloalkoxy group having 1 to 5 carbon atoms include trifluoromethoxy group, pentafluoroethoxy group, perfluoro n propoxy group, perfluoro n butoxy group, perfluoro n amyloxy group, and the like.
  • R 5 R 6 and R 7 are all hydrogen atoms.
  • R 1 and R 2 are each independently a halogen atom, CN NO, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or 1 to 1 carbon atoms.
  • R 3 is preferably a hydrogen atom, preferably a haloalkyl group of 5 or a haloalkoxy group of 1 to 5 carbon atoms.
  • R 1 and R 2 are each independently a halogen atom or a halogen atom, preferably an alkyl group having 1 to 10 carbon atoms.
  • R 1 and R 2 are each independently a chlorine atom or a methyl group, and more preferably a chlorine atom.
  • R 4 represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or 1 carbon atom.
  • a phenyl group that may be substituted with W a naphthyl group that may be substituted with W, or an anthranyl group that may be substituted with W;
  • W is a halogen atom, CN , NO, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or a haloalkoxy group having 1 to 5 carbon atoms.
  • halogen atom examples include the above R 1 to R 3 and Examples thereof are the same as those described for R 5 to R 8 .
  • phenyl group which may be substituted with W include a phenyl group, o-tolyl group, m-trinole group, p-trinole group, o-ethino-lefinino group, m-ethino-lefinenole group.
  • the naphthyl group which may be substituted with W include 1 naphthyl group, 2-naphthinole group, 2-methyl-1 naphthyl group, 3-methyl-1 naphthyl group, 4-methynole 1 naphthyl group, 5 methyl-1 naphthyl group Group, 6 methyl-1 naphthyl group, 7 methyl 1 naphthyl group, 8 methyl-1 naphthyl group, 1-methyl-2 naphthyl group, 3-methyl-2 naphthyl group, 4-methyl-2 naphthyl group, 5 methyl-2 naphthyl group, 6 methyl-2 naphthyl group 7 methyl-2-naphthyl group, 8 methyl-2-naphthyl group and the like.
  • anthranyl group which may be substituted with W include 1 anthranyl group, 2 anthranyl group, 2-methyl-1 anthranyl group, 3-methyl-1 anthranyl group, 4-methyl-1 anthranyl group, 5-methyl-1 anthranyl group 6-methyl-1-anthranyl group, 7-methyl-1-anthranyl group, 8-methyl-1-anthranyl group, 9-methyl-1-anthranyl group, 10-methyl-1-anthranyl group, 1-methyl-2-anthranolin group, 3-methyl-2-anthranyl group, Examples include 4-methyl-2-anthranyl group, 5-methyl-2-anthranyl group, 6-methyl-2-anthranyl group, 7-methyl-2-anthranyl group, 8-methyl-2-anthranyl group, 9-methyl-2-anthranyl group, and 10-methyl-2-anthranyl group.
  • R 4 is substituted with an alkyl group having 1 to 10 carbon atoms or W and V 4 It is preferably a phenyl group, more preferably a W substituted! /, Or even a phenyl group.
  • W is preferably a halogen atom or an alkyl group having 1 to 10 carbon atoms.
  • R 4 is more preferably a phenyl group or a p-tolyl group, preferably a methinole group, an ethyl group, an n-propyl group, a phenyl group, a p-trinole group, or a pentafluorophenyl group. .
  • photoacid generator comprising the cyclohexadiene oxime sulfonate compound represented by the formula [1] include the following compounds.
  • the dye-containing resist composition of the present invention includes a negative type (negative type) resist and a positive type.
  • the dye-containing resist composition of the present invention comprises a photoacid generator (A), a resin (B), a crosslinkable compound (A) comprising a cyclohexagen oxime sulfonate compound represented by the above formula [1]
  • the photoacid generator (A) to be used is one that generates an acid directly or indirectly by light irradiation.
  • the photoacid generator (A) can be used alone or in combination of two or more thereof.
  • the amount introduced is preferably 1 to 300 parts by mass with respect to 100 parts by mass of the resin (B) component. Is selected in the range of 20 to 200 parts by weight. When this amount is less than 1 part by mass, the bridge reaction does not proceed sufficiently, and it is difficult to obtain a desired resist pattern, and when it exceeds 300 parts by mass, the storage stability of the resist composition is poor.
  • the resin (B) used in the negative resist composition is a resin that cures with an acid generated by heat or light irradiation, or a base generated by heat or light irradiation, heat or light irradiation. If it is a photosensitive resin that crosslinks more and the coating film of the unexposed part in the resin can be removed by a developing solution, it is not particularly limited.
  • Examples of the resin (B) include resins having a hydroxyl group or a carboxyl group, for example, acrylic resins such as polybulal alcohol, polyacrylamide, polyacrylic acid, and polymethacrylic acid, polyamic acid, and polybuhlphenol.
  • Derivatives thereof and copolymers thereof copolymers of polymetatalylate and maleic anhydride, phenol resins, novolak resins, polyimides containing hydroxyl groups and / or carboxyl groups, cellulose, cellulose derivatives, starches, Examples include chitin, chitosan, gelatin, zein, sugar skeleton polymer compound, polyamide, polyethylene terephthalate, polycarbonate, polyurethane, and polysiloxane. These resins are used singly or in combination of two or more. Particularly preferably, the resin (B) is polybutanol or a copolymer thereof.
  • Examples of the copolymerizable monomer include acrylic monomers.
  • (Meth) acrylic acid esters include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, hexyl (meth) acrylate, 2-ethyl hexyl ( (Meth) Atarylate, Cyclohexyl (Meth) Atylate, Benzyl (Meth) Atarylate, Dimethylamino (Meth) Atarylate, Hydroxyethyl (Meth) Atarylate, Hydroxypropyl (Meth) Atarylate, Glycidyl (Meth) Atallate is mentioned.
  • Examples of the ethylenically unsaturated carboxylic acid include acrylic acid, methacrylic acid, crotonic acid, maleic acid, fumaric acid, itaconic acid, and acid anhydrides and half esters thereof. Of these, acrylic acid, methacrylic acid, maleic acid, and hydroxypropyl (meth) acrylate are preferable.
  • Polybulfenol a copolymer of polybuhlphenol and the above acrylic monomer has a weight average molecular weight of 1000 to 100,000, and preferably 2000 to 30,000 in terms of developability and adhesion. These can be combined as necessary, and can be used by copolymerizing buluenol with one of the above acrylic monomers, or using buluenol with A copolymer composed of a combination of two or more of the above acrylic monomers can be used.
  • the weight average molecular weight is a relative value in terms of polystyrene.
  • Examples of other compounds used for copolymerization include styrene derivatives such as acrylic acid derivatives, acrylonitrile, methacrylonitrinole, styrene, ⁇ -methylstyrene, ⁇ methylstyrene, ⁇ methylstyrene, ⁇ -methoxystyrene, and ⁇ chlorostyrene. . Of these, styrene is preferred!
  • Polybutanol or a copolymer thereof that is, polyhydroxystyrene or polyhydroxystyrene derivative has a weight average molecular weight of 1000 to 100,000, preferably 2000 to 30,000 from the viewpoint of developability and adhesion. These can be combined as necessary, and can be used alone or in combination of two or more kinds of copolymers.
  • the weight average molecular weight is a relative value in terms of polystyrene.
  • the photoacid generator ( ⁇ ) used when using a resin ( ⁇ ) in a negative resist composition is one that generates acid directly or indirectly by light irradiation. .
  • the crosslinkable compound (C) used for the resin ( ⁇ ) includes a hydroxyl group, a hydroxyalkyl group, (a carbon number of 1 to 5) alkoxy (a carbon atom number of 1 to 5). ) A compound having at least one cross-linking group selected from the group consisting of alkyl groups can be used.
  • an amino resin having a hydroxyl group or an alkoxyl group such as melamine resin, urea resin, guanamine resin, glycoluril formaldehyde resin, succinylamide formaldehyde resin, ethylene urea formaldehyde resin, etc.
  • crosslinkable compound (C) for example, a melamine derivative, a benzoguanamine derivative or glycoluril substituted with a hydrogen nuclear S-methylol group or an alkoxymethyl group of an amino group or both can be used.
  • the melamine derivative and benzoguanamine derivative can exist as a dimer or a trimer. These preferably have an average of 3 to 6 methylol groups or alkoxymethyl groups per triazine ring.
  • Examples of such melamine derivatives or benzoguanamine derivatives include commercially available tria.
  • Methoxymethinorei melamine such as methoxymethinorei melamine, Saimenole 235, 236, 238, 212, 253, 254 etc.
  • Toximethylated Benzoguanamine such as melamine, Cymel 1 123, Toximethylated Benzoguanamine, like Cymel 1123-10, Toximethylinole Benzoguanamine, Saimenole 1125—80
  • a methoxymethylated oxymethylated benzoguanamine (above, manufactured by Nippon Cite Industries Co., Ltd.) is included.
  • glycoluril include salylated glycoluril and the like, and methoxymethylolated glycoluril such as Powderlink 1174 (hereinafter, Nippon Cytec Industries, Ltd.).
  • benzene or phenolic compounds having a hydroxyl group or an alkoxyl group such as 1,3,5-tris (methoxymethyl) benzene, 1,2,4-tris (isopropoxymethinole) benzene, 1,4 bis (sec Butoxymethylol) benzene, 2,6 dihydroxymethyl-p tert butylphenol.
  • a compound containing an epoxy group or an isocyanate group and having a crosslinking group can also be used.
  • Specific examples include, for example, bisphenolacetone glycidyl ether, phenol nopolac epoxy resin, cresol nopolac epoxy resin, triglycidyl isocyanurate, tetraglycidylaminodiphenylene, tetraglycidyl m-xylenediamine, tetraglycidyl 1,3 —Bis (aminoethyl) cyclohexane, tetraphenyldaricidyl etherenoethane, triphenenoreglicidinoreethenoethane, bisphenolenohexanoleoroacetodiglycidinoreethenole, 1,3bis (1— (2,3 epoxy Propoxy) 1-trifluoromethyl-2,2,2 trifluoromethyleno) benzene, 4,4 bis (2,3 epoxycyclopropoxy
  • crosslinkable compounds (C) can be used singly or in combination of two or more.
  • the amount introduced is selected in the range of 1 to 300 parts by weight, preferably 20 to 200 parts by weight, per 100 parts by weight of the resin (B) component. When this amount is less than 1 part by mass, the crosslinking reaction does not proceed sufficiently, and it is difficult to obtain a desired resist pattern. When it exceeds 300 parts by mass, the storage stability of the resist composition is poor. . Therefore, the amount of the crosslinking agent introduced is preferably 1 to 300 parts by mass with respect to 100 parts by mass of the resin component.
  • the dye (D) used in the present invention has a spectral spectrum that is desirable when a color filter is produced, and uses the ability to dissolve in a solvent as it is, or the dye that dissolves in an organized form. I'll do it with power.
  • the dye (D) used in the present invention preferably contains a cationic compound represented by the formula [2].
  • At least one of R 9 and R 1Q has a nitrogen-containing organic group. S is preferable. Particularly, both R 9 and R 1Q have a nitrogen-containing organic group. Is preferred.
  • At least one of the nitrogen-containing organic groups of R 9 and R 1Q has an imino structure (one NH—R 13 ). Particularly, both R 9 and R 1Q have an imino structure (one NH—R 13 ) Is preferable.
  • R 13 represents an organic group, and is preferably an alkyl group such as a methyl group, an ethyl group, or a propyl group, or a substituted or unsubstituted aromatic group, particularly a substituted or unsubstituted aromatic group. It is preferably a group.
  • the aromatic group is preferably a phenyl group, a naphthyl group, an anthryl group, or the like.
  • the substituent of these aromatic groups is an alkyl group such as a methyl group, an ethyl group, or a propyl group, or a halogen atom. Etc. are preferred.
  • R 13 is a phenyl group, o tolyl group, m-tolyl group or p-tolyl group. Are preferred.
  • R u and R 12 at least one of time of preferably fitting one is a hydrogen atom a hydrogen atom and the other is a methyl group, Echiru group, alkyl groups such as propyl group, or a substituted or unsubstituted
  • an aromatic group is preferred.
  • the aromatic group is preferably a phenyl group, a naphthyl group, an anthryl group or the like, and the substituent of these aromatic groups is an alkyl group such as a methyl group, an ethyl group or a propyl group, A halogen atom or the like is preferable.
  • R 11 and R 12 are hydrogen atoms, or, preferably may other while hydrogen atom of R u and R 12 is the aromatic group! /,.
  • cationic compound examples include compounds represented by the following formula.
  • R 14 and R 15 each independently represents a hydrogen atom or a methyl group).
  • the cationic compound may have a resonance structure.
  • the compound of the formula [17] is taken as an example, the formula [18]
  • the dye (D) used in the present invention is preferably an organic salt composed of a cationic compound and an anionic compound.
  • anionic compound as a counter ion of the cationic compound represented by the formula [2] examples include a compound having a phthalocyanine structure, a compound having a pyrazole azo structure, a compound having a pyrazono laser structure and a metal complex structure, xanthene Examples include compounds having a structure.
  • the compound having a phthalocyanine structure is a compound having at least one phthalocyanine structure in one molecule.
  • Phthalocyanine can be used with or without metal, and examples of central metals include Cu, Zn, Al, Ni, and Co.
  • a sulfonic acid group ( -so-) and / or carboxylic acid groups (one coo-).
  • One or a combination of both can be contained in one molecule of phthalocyanine at a ratio of 1 to 4.
  • a sulfonic acid ester group (one SO R 16 , where R 16 represents an aliphatic or aromatic hydrocarbon group having 1 to 20 carbon atoms, an ether group or an ester group).
  • Sulfonic acid amino ester group (one SO NHR 17 , wherein R 17 represents an aliphatic, aromatic hydrocarbon group, ether group or ester group having 1 to 20 carbon atoms), hydroxyl group, It can have a tro group, an amino group, a chlorine atom such as chloro and bromo, and an alkyl group such as a methyl group and an ethyl group, and these nonionic groups can be any one or a combination thereof to form a phthalocyanine.
  • 1 to 4 can be contained in each molecule.
  • the nonionic group is particularly preferably a sulfonic acid amino ester group!
  • a dye (D) used in the present invention comprising a combination of a sulfonic acid group-containing phthalocyanine as an anionic compound and a cationic compound represented by the formulas [5] to [10] 21] can be exemplified.
  • the compound having a pyrazole azo structure is a compound having at least one of a pyrazole part and a azo part in one molecule.
  • the direct bond between the pyrazole moiety and the azo moiety can also exist with other organic groups in between. Both are possible. Examples include compounds in which an aromatic group or aliphatic group such as a phenyl group exists between the pyrazole part and the azo part, and the aromatic group or aliphatic group has a sulfonic acid group or other substituent. It is done.
  • the compound having a pyrazole azo structure preferably has a sulfonic acid group (-so-) and / or a carboxylic acid group (one COO-) as an anion component.
  • Either one or a combination of both may be contained in a ratio of 1 to 4 in one molecule of the compound having a pyrazole azo structure.
  • anionic group a sulfonic acid group can be preferably used.
  • a sulfonic acid amino ester group (one SO NHR 18 , wherein R 18 is an aliphatic, aromatic hydrocarbon group, ether group or ester group having 1 to 20 carbon atoms).
  • R 18 is an aliphatic, aromatic hydrocarbon group, ether group or ester group having 1 to 20 carbon atoms.
  • a hydroxyl group, a nitro group, an amino group, a chlorine atom such as chloro and bromo, an alkyl group such as a methyl group and an ethyl group, and these nonionic groups are either one or these In combination, it can be contained in a ratio of 1 to 4 per molecule of the compound having a pyrazole azo structure.
  • a dye (D) used in the present invention comprising a combination of a compound having a sulfonic acid group-containing pyrazole azo structure as an anionic compound and a cationic compound represented by the formulas [5] to [18], 22] to [24] can be exemplified.
  • the compound having a pyrazole azo structure and a metal complex structure is a compound in which a compound having an anionic group-containing virazo azo structure forms a complex with a metal.
  • the compound having an anionic group-containing pyrazole azo structure and the metal have a force S of forming a complex at a ratio of 2 to 4: 1 (molar ratio), and a preferable ratio is 2: 1 (molar ratio).
  • the metal existing in the center is preferably a force Co such as Cu, Zn, Al, Ni, Co and the like.
  • a compound having a pyrazole azo structure and a metal complex structure preferably has a sulfonic acid group (SO) and / or a carboxylic acid group (COO-) as an anion component. These can be contained in a ratio of 1 to 4 in one molecule of a compound having a pyrazole azo structure, either one or a combination of both.
  • a sulfonic acid group can be preferably used as the anionic group.
  • a sulfonic acid amino ester group (one SO NHR 19 , where R 19 is an aliphatic, aromatic hydrocarbon group, ether group or ester group having 1 to 20 carbon atoms).
  • R 19 is an aliphatic, aromatic hydrocarbon group, ether group or ester group having 1 to 20 carbon atoms.
  • a hydroxyl group, a nitro group, an amino group, a chlorine atom such as chloro and bromo, an alkyl group such as a methyl group and an ethyl group, and these nonionic groups are either one or these In combination, it can be contained in a ratio of 1 to 4 per molecule of the compound having a pyrazole azo structure.
  • an alkyl group such as a nitro group, a hydroxyl group, a methyl group, and an ethyl group can be preferably used.
  • a dye used in the present invention comprising a combination of a compound having a metal complex structure and a sulfonic acid group-containing pyrazole azo structure as an anionic compound and a cationic compound represented by the formula [5] to formula [18] ( As D), it is possible to exemplify the one of the formula [25]! And the formula [30].
  • R 2 ° represents an aliphatic or aromatic hydrocarbon group, ether group or ester group having 1 to 20 carbon atoms. ), A hydroxyl group, a nitro group, an amino group, a chlorine atom such as chloro and bromo, and an alkyl group such as a methyl group and an ethyl group. These nonionic groups may be any one or a combination thereof.
  • the compound having a pyrazole azo structure can be contained in a ratio of 1 to 4 in one molecule.
  • a compound having a xanthene structure has at least one xanthene structure in one molecule. It is a compound.
  • the compound having a xanthene structure preferably has a sulfonic acid group (one S O—) and / or a carboxylic acid group (one COO—) as an anion component. These can be contained in a ratio of 1 to 3 in one molecule of a compound having a pyrazole azo structure, either or a combination of both.
  • a carboxylic acid group can be preferably used as the anionic group.
  • a sulfonic acid amino ester group (one SO NHR 21 , wherein R 21 is an aliphatic, aromatic hydrocarbon group, ether group or ester group having 1 to 20 carbon atoms).
  • R 21 is an aliphatic, aromatic hydrocarbon group, ether group or ester group having 1 to 20 carbon atoms.
  • a hydroxyl group, a nitro group, an amino group, a chlorine atom such as chloro and bromo, an alkyl group such as a methyl group and an ethyl group, and these nonionic groups are either one or these In combination, it can be contained in a ratio of 1 to 3 per molecule of the compound having a xanthene structure.
  • the dye (D) used in the present invention comprising a combination of a compound having a xanthene structure as an anionic compound and a cationic compound represented by the formulas [5] to [18] is represented by the formula [31] to the formula [35]. Can be illustrated.
  • a commercial item can be used for the dye (D) used for this invention.
  • These dyes can be easily synthesized by known methods. For example, it can be obtained by a method of reacting an amine corresponding to the structure of the above formulas [5] to [18] with a dye molecule (matrix) having a sulfonic acid group or a carboxylic acid group. That is, a compound having a phthalocyanine structure having a sulfonic acid group or a carboxylic acid group, a compound having a pyrazole azo structure, a compound having a metal complex structure and a pyrazole azo structure, or a compound having a xanthene structure.
  • the solution can be synthesized by reacting with the amine required for salt formation in the desired molar ratio to precipitate a sparingly soluble salt in water. When the dye salt is soluble in water, the salt is obtained by salting out.
  • an aqueous solution of an amine hydrochloride corresponding to the structure of the above formulas [5] to [18] is added to an aqueous solution of the above dye having sodium sulfonate or sodium carboxylate, and reacted. [5] to produce a dye having a cationic compound of formula [18].
  • the dye (D) used in the present invention can be further used in combination with an arbitrary dye.
  • these dyes include acid dyes, oil-soluble dyes, disperse dyes, reactive dyes, and direct dyes.
  • azo dyes benzoquinone dyes, naphthoquinone dyes, anthraquinone dyes, cyanine dyes, squarylium dyes, croconium dyes, merocyanine dyes, stilbene dyes, diphenylmethane dyes, triphenylmethane dyes, fluoranes Dyes, spiropyran dyes, phthalocyanine dyes, indigo dyes, fulgide dyes, nickel complex dyes and azulene dyes.
  • Specific examples of color index numbers include the following. C. I. Solvent Yellow
  • the dye (D) exhibits an optical characteristic having a region showing a transmittance of 70% or more in a wavelength region of 400 to 700 nm and a region showing a transmittance of 10% or less, and 200
  • the resist composition of the present invention in which the change in transmittance is preferably within 5% even at a temperature of ⁇ C, and the color filter produced from the resist composition exhibit similar optical characteristics.
  • the dye-containing resist composition of the present invention is applied to a substrate, then baked at a temperature of 50 to 150 ° C, exposed and developed, and this baking temperature is set to 200 to 270 ° C (200 ° C). Even if baked at a high temperature of 30 minutes for C and 30 seconds at 270 ° C), it is 400! /, And the transmittance change with time of the portion showing a transmittance of 70% or more in the 700 nm wavelength region is high-temperature baking. Within 5% is preferred compared to before performing.
  • the amount of the dye (D) introduced is a solid comprising the photoacid generator (A), the resin (B), the crosslinkable compound (C), and the dye (D). It is selected in the range of 1 to 90% by mass with respect to the whole minute (100%).
  • the amount of dye introduced is small, it becomes difficult to develop a desired spectral spectrum when the resist film is thinned, and when the amount of dye introduced is large, the storage stability of the resist composition is poor.
  • a dye having a cationic compound represented by the above formula [2], and further a dye comprising a cationic compound represented by the above formula [2] and an anionic compound As a matter of course, the introduction amount of the above dye (the concentration of the dye in the entire solid content) can be used at a low concentration of several mass%, but it is set to a high concentration of 30 to 90 mass%. The dye is sufficiently soluble.
  • the solvent (E) used in the dye-containing resist composition of the present invention is, for example, acetone, methanol monoethanol, ethanol, isopropyl alcohol, methoxymethylpentanol, dipentene, ethyl amyl ketone, methyl nonyl ketone, methyl ester.
  • Tilketone methyl isoamyl ketone, methinoreisopropenoleketone, methinoresenoresorenolev, ethinoresenoresonolev, methinoreserosolorebu Cetate, ethyl acetate sorb acetate, butyl carbitol, ethyl carbitol, ethylene glycolate, ethylene glycol monoacetate, ethylene glycol monoacetopropylene oleore, ethylene glycol ole monobutenoate, propylene glycol nore, propylene glycol Nole monoacetate, propylene glycol nole monomethylenoate, propylene glycol nore tert butinoleate nore, dipropylene glycol nole monomethinoatenore, diethylene glycol nore, diethylene glycol nore monoacetate, diethylene glyconoremino chinenoate nore, dipropylene Glyconole monoacetate monomethylenoateolene
  • ketol solvents are particularly preferred for compatibility with the dye (D) used in the present invention.
  • ketol include / 3-hydroxyketone, and specific examples thereof include 4-hydroxy-4-methyl-2-pentanone.
  • this ketol solvent can be used alone, but it is preferable to select a solvent containing the ketol solvent in a ratio of 10% by mass or more in the total solvent.
  • the photoacid generator (A), the resin (B), the crosslinkable compound (C) and the dye (D) are combined with the photoacid generator (A), the resin (B ),
  • the crosslinkable compound (C), the dye (D), and the solvent (E) are contained in a proportion, that is, a solid content concentration of 5 to 50% by mass, preferably 10 to 30% by mass.
  • a proportion that is, a solid content concentration of 5 to 50% by mass, preferably 10 to 30% by mass.
  • the dye-containing resist composition of the present invention may contain a surfactant for the purpose of improving the wettability and flatness of the resist film.
  • surfactants include fluorine-based surfactants, silicone-based surfactants, and noion-based surfactants.
  • F-top EF301, EF303, EF352 manufactured by Tochem Products Co., Ltd.
  • MegaFac F171, F173, R-30 manufactured by Dainippon Ink Co., Ltd.
  • Florard FC4 30, FC431 Sumitomo 3EM Co., Ltd.
  • Asahi Guard AG710, Surflon S-382, SC101, SC102, SC103, SC104, SC105, SC106 manufactured by Asahiishi Shoko Co., Ltd.
  • the ratio of these surfactants to be used is preferably 0.01 to 2 parts by mass, more preferably 0.01 to 1 part by mass with respect to 100 parts by mass of the resin (B) component. If the surfactant content exceeds 2 parts by mass, the resist film becomes uneven, and if it is less than 0.01 parts by mass, striations are likely to occur in the resist film.
  • an adhesion promoter can be contained.
  • adhesion promoters include, for example, trimethylchlorosilane, dimethylvinylchlorosilane, methyldiphenylchlorosilane, chloromethyldimethylchlorosilane.
  • Chlorosilanes such as orchid, alkoxysilanes such as trimethylmethoxysilane, dimethyljetoxysilane, methyldimethoxysilane, dimethylvinylethoxysilane, diphenyldimethoxysilane, phenyltriethoxysilane, hexamethyldisilazane, N, N, Bis (trimethylsilyl) urea, dimethyltrimethylsilylamine, silazanes of trimethylsilylimidazoles, butyltrichlorosilane, ⁇ -chloropropylpropylmethoxysilane, ⁇ -aminopropyltriethoxysilane, ⁇ -methacryloxypropyltrimethoxysilane ⁇ -glycidoxyprovir trimethoxysilane and other silanes, benzotriazole, benzimidazole, indazole, imidazole, 2-mercaptobensimidazole
  • the use ratio of these adhesion promoters is usually 20 parts by mass or less, preferably 0.05 to 10 parts by mass, and particularly preferably 1 to 10 parts by mass with respect to 100 parts by mass of the resin (i) component. It is.
  • UV absorbers and antioxidants that enhance light stability, and compatibilizers that suppress dye precipitation include polyoxyethylene octyl ether compounds, polyoxyethylene lauryl ether compounds, polyoxyethylene alkyl ( 12 to 13 carbon atoms ether compound, polyoxyethylene secondary alkyl (12 to 14 carbon atoms) ether compound, polyoxyethylene alkyl (13 carbon atoms) ether compound, polyoxyethylene cetyl ether compound, polyoxyethylene Stearyl ether compounds, polyoxyethylene oleyl ether compounds, polyoxyethylene decyl ether compounds, polyoxyalkylene alkyls (11 carbon atoms!
  • ether compounds such as ether compounds and polyoxyalkylene cetyl ether compounds, alkyls such as polyoxyethylene lauryl amino ether compounds, polyoxyethylene stearyl amino ether compounds and polyoxyethylene oleylamino ether compounds Amino ether compound, polyoxyethylene lauric acid Alkylamide compounds such as amide ether compounds, polyoxyethylene stearic acid amide ether compounds, polyoxyethylene oleic acid amide ether compounds, lauric acid diethanolamide compounds, stearic acid diethanolamide compounds, oleic acid diethanolamide compounds, Polyoxyethylene polystilphenyl ether compound
  • Polysyl phenyl ether formamide condensates polyoxyethylene monostyryl phenyl ether compounds, polyoxyethylene distyryl phenyl ether compounds, polyoxyethylene naphthyl ether compounds and other aryl phenyl ether compounds, glycerin monolaurate compounds, Glycerin monostearate compound, glycerin monooleate compound, glycerin fatty acid ester compound such as glycerol triolate compound, sorbitan monolaurate compound, sorbitan monopalmitate compound, sorbitan monostearate compound, sorbitan tristearate compound, sorbitan Sorbitanate compounds such as monooleate compounds, sorbitan trioleate compounds, polyoxyethylene dilaurate compounds, polyoxyesters Len laurate compound, polyoxyethylene stearate compound, polyoxyethylene distearate compound, polyoxyethylene dioleate compound, fatty acid ether ester compound such as polyoxyethylene o
  • Monool type polyether compound such as ether compound, polyoxyalkylene oleyl ether compound, diol type polyether compound such as polyoxyethylene polyoxypropylene condensate, trimethylolpropane tris (polyoxyalkylene) ether
  • polyol type polyether compounds such as polyoxyalkylene glyceryl ether compounds, methyl laurate compounds, methyl oleate compounds, isopyl pyrmyristate compounds, butyl stearate compounds, octyl palmitate compounds, Octyl stearate compound, Lauryl oleate compound, Isotridecyl stearate compound, Oleolelate compound, Dioleyl adipate compound, Trimethylolpropane Tridecanoate compound, Trimethylolpropane trilaurate compound, Pentaerythritol monorudiolate compound, Fatty acid alkyl ester compounds such as pentaerythrito
  • sulfonic acid type compounds such as dioctylsulfosuccinate compounds, oleic acid sulfated oil compounds, castor sulfated compounds, octyl sulfate compounds, lauryl sulfate compounds, alkyl sulfate compounds, alkyl ether sulfate compounds, etc.
  • cellulose, cellulose derivatives, and sugar skeleton polymer compounds such as dioctylsulfosuccinate compounds, oleic acid sulfated oil compounds, castor sulfated compounds, octyl sulfate compounds, lauryl sulfate compounds, alkyl sulfate compounds, alkyl ether sulfate compounds, etc.
  • the proportion of the compatibilizer used is 0.001 to 100 parts by mass of resin (B) component 100 parts by mass.
  • the compatibilizer does not interfere with the pattern shape, it can be used in an amount of 20 parts by mass or more.
  • photosensitizers can be used as photosensitizers.
  • a method for producing a color filter using the dye-containing resist composition of the present invention is not particularly limited, and examples thereof include the following methods.
  • the resist composition of the present invention is prepared at a rotational speed to obtain a desired resist film thickness by a spinner method. Apply on recon wafer or glass substrate and perform soft beta (firing). The soft beta should be conducted for 30 seconds to 10 minutes in the temperature range of 50 to 150 ° C, as long as the solvent is evaporated. After that, exposure is performed through a mask at an exposure amount of about 10 to 3000 mj / cm 2 . For the exposure, for example, ultraviolet rays such as a mercury lamp, far ultraviolet rays, electron beams, or X-rays are used. When a pattern is formed using a negative resist composition after exposure, heating (P EB (post exposure beta)) is preferably performed.
  • P EB post exposure beta
  • PEB crosslinking with an acid or base generated by exposure further proceeds, and the difference in the solubility of the developing solution from the unexposed area is further widened to improve the resolution contrast.
  • PEB should be in the temperature range of 50 to 170 ° C for 30 seconds! /, And preferably for 5 minutes! /.
  • the developing method can be carried out by a known method such as a paddle method, a dating method, or a spray method without any particular limitation.
  • the development temperature is 20! /, And it is preferable to immerse in a developer solution preferably between 50 ° C for 10 seconds to 10 minutes.
  • an organic solvent or an alkaline aqueous solution can be used as the developer.
  • an organic solvent or an alkaline aqueous solution can be used. Specific examples include isopropyl alcohol, propylene glycol monomethyl ether, ethylamine aqueous solution, n-propylamine aqueous solution, jetylamine aqueous solution, diethyl n-propylamine aqueous solution, triethylamine aqueous solution, methyljetylamine aqueous solution, diethanolamine aqueous solution, triethanol.
  • Examples thereof include an aqueous solution of amine, an aqueous solution of tetramethylammonium hydroxide, an aqueous solution of sodium hydroxide, an aqueous solution of potassium hydroxide, an aqueous solution of sodium carbonate, an aqueous solution of sodium bicarbonate, an aqueous solution of sodium silicate, and an aqueous solution of sodium metasilicate.
  • a surfactant to the developer in order to enhance the removability of the unexposed areas.
  • Specific examples include polyoxyethylene octyl ether compounds, polyoxyethylene lauryl ether compounds, polyoxyethylene alkyl (12 or 13 carbon atoms) ether compounds, polyoxyethylene secondary alkyl (12 to 14 carbon atoms).
  • Ether compounds polyoxyethylene alkyl (13 carbon atoms) ether compounds, polyoxyethylene cetyl ether compounds, polyoxyethylene stearyl ether compounds, polyoxyethylene oleyl ether compounds, polyoxyethylene decyl ether compounds, polyoxyalkylenes Alkyl (11 carbon atoms!
  • etherification Compounds polyoxyalkylene secondary alkyl (carbon atoms of 12 to 14) ether compounds, alkyl ether compounds such as polyoxyalkylene cetyl ether compounds, polyoxyethylene lauryl amino ether compounds, polyoxyethylene stearyl amino ethers Compounds, alkylamino ether compounds such as polyoxyethylene oleylamino ether compounds, polyoxyethylene lauric acid amide ether compounds, polyoxyethylene stearic acid amide ether compounds, polyoxyethylene oleic acid amide ether compounds, Alkylamide ether compounds such as lauric acid diethanolamide compound, stearic acid diethanolamide compound, oleic acid diethanolamide compound, polyoxyl ether compound, polyoxyalkylene Polystyryl phenyl ether formamide condensate, polyoxyethylene monostyryl phenyl ether compound, polyoxyethylene distyryl phenyl ether compound, polyoxyethylene naphthyl ether compound
  • Sorbitan ether ester compounds such as polyoxyethylene sorbitan monolaurate compounds, polyoxyethylene sorbitan monostearate compounds, polyoxyethylene sorbitan monooleate compounds, polyoxyethylene sorbitan trioleate compounds,
  • polyoxyalkylene alkyl (carbon atoms of 14! /, 15) ether compounds monool-type polyether compounds such as polyoxyalkylene oleyl ether compounds
  • Diol type polyether compounds such as polyoxyethylene polyoxypropylene condensate
  • polyol type polyether compounds such as trimethylolpropane tris (polyoxyalkylene) ether compound
  • polyoxyalkylene glyceryl ether compound methyl laurate compound, methyl oleate compound, Isopropyl myristate compound, butyl stearate compound, octyl palmitate compound, octyl stearate compound, laurylololeate compound, isotridecyl stearate compound, oleyllate compound, dioleyl adipate compound, trimethylolpropane tridecanoate compound, trimethylo Propanetrilaurate compound, pentaerythritol diolate compound,
  • the preferred concentration of the alkali developer is 0.001 to 10% by mass for the alkali component and 0.001 to 10% by mass for the surfactant component. If the alkali component is too high, the developability is too strong. In the case of the negative type, the unexposed area penetrates to the unexposed area. If the pattern surface is rough, the developability cannot be obtained. On the other hand, if the surfactant component is too high, foaming tends to occur and development unevenness tends to occur, and if it is too low, developability cannot be obtained.
  • the color filter produced using the dye-containing resist composition of the present invention can be suitably used for a liquid crystal display device, an LED (light emitting diode) display device, a solid-state imaging device, and the like. It is preferably used as a solid-state image sensor.
  • the present invention also provides a cyclohexagen-based oxime sulfonate compound represented by the formula [3].
  • R 1 and R 2 are each independently a halogen atom, a CN NO alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or 1 to 1 carbon atoms.
  • R 3 represents a hydrogen atom, a halogen atom, a nitro group, a CN group, an alkyl group of 1 to 10 carbon atoms, or an alkyl group of 1 to 5 carbon atoms.
  • each R 3 may be the same as each other or in addition, when R 3 is adjacent to each other, the two adjacent R 3 are —CH CH —CH 2 O— —CH N (R 8 ) — —CH 2 CH 2 CH 2 CH 2 O— CH CH N (R 8 ) CH CH CH CH CH CH CH O— CH CH CH N (R 8 ) — CH CH CH CH CH CH CH CH
  • R 4 may be an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, a haloalkoxy group having 1 to 5 carbon atoms
  • R 8 represents a phenyl group which may be substituted with W, a naphthyl group which may be substituted with W, or an anthranyl group which may be substituted with W.
  • R 8 represents a hydrogen atom or a carbon atom having 1 to 10 carbon atoms.
  • W represents a halogen atom, CN NO, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkyl group having 1 to 5 carbon atoms, or 1 to 1 carbon atoms.
  • 5 represents a haloalkoxy group
  • n is 1 2 3 Or represents an integer of 4.
  • a halogen atom an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkoxy group having 1 to 5 carbon atoms, a phenyl group optionally substituted by W, W
  • W Specific examples of the naphthyl group optionally substituted with and the anthranyl group optionally substituted with W include the same groups as those described for R 1 to R 4 above.
  • the present invention also provides a cyclohexadiene-based oxime compound represented by the formula [4] as an intermediate for producing the compound represented by the formula [3].
  • R 1 and R 2 are each independently a halogen atom, a CN NO alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, or 1 to 1 carbon atoms.
  • R 3 represents a hydrogen atom, a halogen atom, a nitro group, a CN group, an alkyl group of 1 to 10 carbon atoms, or an alkyl group of 1 to 5 carbon atoms.
  • each R 3 may be the same as each other or in addition, when R 3 is adjacent to each other, the two adjacent R 3 are —CH CH —CH 2 O— —CH N (R 8 ) — —CH 2 CH 2 CH 2 CH 2 O— CH CH N (R 8 ) CH CH CH CH CH CH CH O— CH CH CH N (R 8 ) — CH CH CH CH CH CH CH CH
  • R 8 represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms
  • n represents an integer of 1 2 3 or 4.
  • halogen atom an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkoxy group having 1 to 5 carbon atoms, and a phenyl group optionally substituted by W
  • a halogen atom an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a haloalkoxy group having 1 to 5 carbon atoms, and a phenyl group optionally substituted by W Examples thereof include the same groups as those described for R 1 to R 4 above.
  • the cyclohexadiene oxime sulfonate compound represented by the formula [3] can be produced by a production method including the following steps. [Formula 15] one R1 (f [pi basic acid R 1 ⁇ >"R4S02CI R 1 ()" 2 R 2 CN bases R 2 0N
  • an intermediate oxime compound is obtained by reacting a substituted phenylacetonitrile compound (PAN) and a nitrobenzene compound (NB) in the presence of a base, followed by acidification.
  • OC is reacted with a sulfonyl chloride compound (SC) in the presence of a base to produce the desired cyclohexadiene oxime sulfonate compound (SCHC).
  • substituted phenylacetonitrile compound (PAN) in the first step 2, 6 difluorophenylacetonitrile, 2, 6 diclonal phenylacetonitrile, 2, 6 dibuphthyl phenylacetonitrile, 2 , 6 Jodophenylacetonitrile, 2, 6 Dicyanophenoxyacetonitrile, 2, 6 Dinitrophenylacetonitrile, 2, 6 Dimethylphenylacetonitorinole, 2, 6 Dimethoxyphenenoleacetonitrinole, 2, 6 Examples include 6-difluoromethoxyphenylacetonitrile, 2-fluoro-6-methylphenylacetonitrile, 2-chloro-6-methylphenylacetonitrile, 2-bromo-6-methylphenylacetonitrile, and the like. Of these, 2,6-dichlorophenylnitrile and 2,6 dimethylphenylnitrile are particularly preferred.
  • nitrobenzene compound (NB) examples include nitrobenzene, 2-chloronitrite benzene, 3 chloronitrobenzene, 2 cyanonitrobenzene, 3 cyanonitrobenzene, 2 methinorenitrobenzene, 3 methinorenitrobenzene, 2- (i —Propinole) Nitrobenzene, 3— (i Propinole) Nitrobenzene, 2 Methoxy nitrobenzene, 3 Methoxynitrate Mouth benzene, 2 Trifunoleolomethino nitrobenzene, 3 Trifunoleolomethino nitrobenzene, 2 Trifluoromethoxynitrobenzene 3 trifluoromethoxynitrobenzene and the like. Also, the 2nd and 3rd positions are joined together to form a ring with 2 to 5 carbon atoms (oxygen atom or As the group that may form a nitrogen atom), for example, a compound of the following
  • nitrobenzene, 2-chloronitrobenzene, 3-chloronitrobenzene, 2-methino nitrobenzene, 3-methino nitrobenzene, 2- (i-propinole) nitrobenzene, 3- (i -Propyl) nitrobenzene and the like are preferred.
  • the amount used is 0.8 for PAN. : Booster preference.
  • alkali metal or alkaline earth metal hydroxides, carbonates, organic acid salts and the like can be used as the base. Specifically, from the viewpoint of reactivity and economy, sodium hydroxide or lithium hydroxide Is preferred.
  • the amount used is preferably 2 to 5 equivalents to PAN.
  • the reaction solvent is preferably an aliphatic alcohol having 1 to 5 carbon atoms such as methanol or ethanol.
  • the reaction temperature is preferably -20 to 150 ° C, particularly 0 to 100 ° C.
  • water is added to the reaction solution, acidified with an inorganic or organic acid, extracted with ethyl acetate and concentrated, and the resulting crude product is purified by recrystallization or column chromatography to obtain the desired OC.
  • hydrochloric acid or acetic acid is used as the inorganic acid or organic acid.
  • organic bases such as triethylamine, pyridine, 4-N, N dimethylaminopyridine (DMA P) can be used.
  • the amount used is preferably 1 to 1.1 equivalent times the amount of SC.
  • reaction solvent examples include the number of carbon atoms such as toluene, xylene, ethylbenzene, and cumene.
  • the reaction temperature is preferably -20 to 100 ° C, particularly 0 to 80 ° C.
  • concentration yields a brown solid, which is then recrystallized or purified by column chromatography using silica gel to produce the desired cyclohexadiene oxime sulfonate compound (SCHC). .
  • Each of the above reactions can be carried out batchwise or flow-through, and can be carried out at normal pressure or under pressure.
  • n is normal, “i” is iso, “s” is secondary, “t” is tertiary, “c” is cyclo, “o” is ortho.
  • M represents meta, “p” represents para, “Me” represents a methyl group, “Et” represents an ethyl group, and “Pr” represents a propyl group.
  • the measuring device and conditions for each physical property in the examples are as follows.
  • Measuring instrument Automatic melting point measuring device, FP62 (Metler Toledo Co., Ltd.)
  • VP8000 manufactured by Nippon Soda Co., Ltd., the component is polybutanol.
  • Megafac R-30 Dainippon Ink Chemical Co., Ltd.
  • 4 hydroxy-4-methyl-2-pentanone (30 g) was added as a solvent and stirred at room temperature. No insoluble matter was found in the reaction solution, and the solution was uniform.
  • the composition was filtered using a 0.2 Hm PTFE (polytetrafluoroethylene) filter, and the composition was applied onto a glass substrate using a spin coater.
  • the film was baked on a hot plate (soft beta) at 110 ° C for 1 minute to form a coating film with a thickness of 1.02 ⁇ (measured with an interference film thickness meter).
  • This coating film was irradiated with ultraviolet rays having an irradiation dose of 600 mj / cm 2 at 365 nm by an ultraviolet irradiation device. Subsequently, PEB was performed on a hot plate at 120 ° C for 1 minute. Thereafter, post-beta was performed on a hot plate at 200 ° C. for 5 minutes, and the transmittance (transmittance at 400 nm) of the glass substrate on which the resist was formed was measured with a spectrophotometer.
  • the composition was filtered using a 0.2 m PTFE filter, and the composition was applied onto a glass substrate using a spin coater.
  • the film was baked on a hot plate at 110 ° C for 1 minute (soft beta) to form a coating film with a thickness of 1.02 ⁇ m (measured with an interference film thickness meter).
  • This coating film was irradiated with ultraviolet rays having an irradiation dose of 600 mj / cm 2 at 365 nm by an ultraviolet irradiation device. Subsequently, PEB was performed on a hot plate at 120 ° C for 1 minute. After that, post-beta was performed on a hot plate at 200 ° C for 5 minutes, and the resist was deposited on the film. The transmittance of the glass substrate (transmittance at 400 nm) was measured with a spectrophotometer.
  • This coating film was irradiated with ultraviolet rays having an irradiation dose of 600 mj / cm 2 at 365 nm by an ultraviolet irradiation device. Subsequently, PEB was performed on a hot plate at 120 ° C for 1 minute. Thereafter, post-beta was performed on a hot plate at 200 ° C. for 5 minutes, and the transmittance (transmittance at 400 nm) of the glass substrate on which the resist was formed was measured with a spectrophotometer.
  • VP8000 manufactured by Nippon Soda Co., Ltd., the component is polybutanol.
  • Weight average molecular weight 8000 (polystyrene conversion)) 5 g, CGI1325 (manufactured by Ciba Specialty Chemicals Co., Ltd.) 0.25 g of thiophenoxime sulfonate photoacid generator) and 0.012 g of MegaFac R-30 (Dainippon Ink Chemical Co., Ltd.) as the surfactant were added, and 4-hydroxy-4-methyl-2 as the solvent. 30 g of pentanone was added and stirred at room temperature.
  • the composition was filtered using a 0.2 m PTFE filter, and the composition was applied onto a glass substrate using a spin coater.
  • the film was baked on a hot plate at 110 ° C for 1 minute (soft beta) to form a coating film with a thickness of 1.02 and im (measured with an interference film thickness meter).
  • This coating film was irradiated with ultraviolet rays having an irradiation dose of 600 mj / cm 2 at 365 nm by an ultraviolet irradiation device. Subsequently, PEB was performed on a hot plate at 120 ° C for 1 minute. afterwards Post-beta was performed on a hot plate at 200 ° C for 5 minutes, and the transmittance (transmittance at 400 nm) of the glass substrate on which this resist was formed was measured with a spectrophotometer.
  • VP8000 manufactured by Nippon Soda Co., Ltd., the component is polybutanol.
  • Weight average molecular weight 8000 (polystyrene conversion)) 5 g, CGI1397 (manufactured by Ciba Specialty Chemicals Co., Ltd.) 0.25 g of thiophenoxime sulfonate photoacid generator) and 0.012 g of MegaFac R-30 (Dainippon Ink Chemical Co., Ltd.) as the surfactant were added, and 4-hydroxy-4-methyl-2 as the solvent.
  • Pentanone (30 g) was added and stirred at room temperature.
  • the composition was filtered using a 0.2 m PTFE filter, and the composition was applied onto a glass substrate using a spin coater.
  • the film was baked on a hot plate at 110 ° C for 1 minute (soft beta) to form a coating film with a thickness of 1.02 and im (measured with an interference film thickness meter).
  • This coating film was irradiated with ultraviolet rays having an irradiation dose of 600 mj / cm 2 at 365 nm by an ultraviolet irradiation device. Subsequently, PEB was performed on a hot plate at 120 ° C for 1 minute. Thereafter, post-beta was performed on a hot plate at 200 ° C. for 5 minutes, and the transmittance (transmittance at 400 nm) of the glass substrate on which the resist was formed was measured with a spectrophotometer.
  • Table 1 shows the transmittance results of the resists produced in Examples 4 to 6 and Comparative Examples 1 and 2. [table 1]
  • Comparative Example 2 4 2% As shown in Table 1, the resist (Examples 4 to 6) prepared using the photoacid generator of the cyclohexagen-based oxime sulfonate compound of the present invention is shown in Table 2002. — Photoacid of the present invention having higher post-beta transmittance than a resist (Comparative Examples 4 to 6) prepared using a photoacid generator comprising a thiophenoxime sulfonate compound described in Japanese Patent No. 508774. It can be seen that the generator is less colored by exposure and heating. Next, the effect of producing a color filter using the dye-containing resist composition of the present invention will be shown.
  • VP8000 manufactured by Nippon Soda Co., Ltd., the component is polybutanol.
  • Weight average molecular weight 8000 (polystyrene equivalent)) is 1.54 g
  • dye formula [21] is 1.9 g
  • As a solvent 23.756 g of propylene glycol monomethyl ether was added and stirred at room temperature. No insoluble matter was found in the reaction solution, and the solution was uniform.
  • This coating film was irradiated with ultraviolet rays having an irradiation dose of 600 mj / cm 2 at 365 nm by an ultraviolet irradiation device. Subsequently, PEB was performed on a hot plate at 120 ° C for 1 minute. After that, post-beta was performed on a hot plate at 200 ° C for 5 minutes, and the resist was deposited on the film. The transmittance of the glass substrate (transmittance at 400 nm) was measured with a spectrophotometer.
  • this composition was apply
  • This coating film was irradiated with ultraviolet rays having an irradiation dose of 600 mJ / cm 2 at 365 nm by an ultraviolet irradiation device. Subsequently, PEB was performed on a hot plate at 120 ° C for 1 minute. Thereafter, the film thickness was measured using an interference type film thickness meter.
  • This film was statically developed at room temperature for 40 seconds using a developer NMD-3 (manufactured by Tokyo Ohka Kogyo Co., Ltd.), and the film thickness was measured again using an interference film thickness meter.
  • the film thickness before and after development was compared, and the remaining film ratio after development was calculated.
  • VP8000 manufactured by Nippon Soda Co., Ltd., the component is polybutanol.
  • Weight average molecular weight 8000 (polystyrene equivalent)) is 1.54 g
  • dye formula [21] is 1.9 g
  • As a solvent 23.756 g of propylene glycol monomethyl ether was added and stirred at room temperature. No insoluble matter was found in the reaction solution, and the solution was uniform.
  • This coating film was irradiated with ultraviolet rays having an irradiation dose of 600 mj / cm 2 at 365 nm by an ultraviolet irradiation device. Subsequently, PEB was performed on a hot plate at 120 ° C for 1 minute. Thereafter, post-beta was performed on a hot plate at 200 ° C. for 5 minutes, and the transmittance (transmittance at 400 nm) of the glass substrate on which the resist was formed was measured with a spectrophotometer.
  • this composition was apply
  • the UV irradiation device applied this coating film with a dose of 300mj / c at 365nm. Irradiated with ultraviolet rays of m 2 .
  • PEB was performed on a hot plate at 120 ° C for 1 minute. Thereafter, the film thickness was measured using an interference type film thickness meter.
  • This film was statically developed at room temperature for 30 seconds using a developer NMD-3 (manufactured by Tokyo Ohka Kogyo Co., Ltd.), and the film thickness was measured again using an interference film thickness meter.
  • the film thickness before and after development was compared, and the remaining film ratio after development was calculated.
  • Table 2 shows the transmittance of the resists produced in Example 7 and Comparative Example 3.
  • the resist (Example 7) prepared using the dye-containing resist composition of the present invention is a thiophenoxime sulfonate compound described in JP-T-2002-508774.
  • the dye-containing resist composition of the present invention which has higher post-beta transmittance, is more effective for color filters than a resist prepared using a dye-containing resist composition containing I understand.
  • Table 3 shows the remaining film ratio of the color filters manufactured in Example 7 and Comparative Example 3.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)

Abstract

[PROBLÈMES] Proposer une composition de résist contenant un colorant qui peut fournir un filtre de couleur supprimé dans la coloration à la région visible (400 à 730 nm). [MOYENS POUR RÉSOUDRE LES PROBLÈMES] L'invention concerne une composition de résist contenant un colorant, contenant un générateur de photoacide, comprenant un composé de sulfate d'oxime de type cyclohexadiène représenté par la formule [1], [1] dans laquelle R1, R2, R5, R6 et R7 représentent indépendamment un atome d'hydrogène, un atome d'halogène, CN, NO2, un groupe alkyle ayant 1 à 10 atomes de carbone, un groupe alkoxy ayant 1 à 5 atomes de carbone, ou similaires ; R3 représente un atome d'hydrogène, un atome d'halogène, un groupe nitro, un groupe CN, un groupe alkyle ayant 1 à 10 atomes de carbone, un groupe alcoxy ayant 1 à 5 atomes de carbone, ou similaires ; R4 représente un groupe alkyle ayant 1 à 10 atomes de carbone, un groupe alkoxy ayant 1 à 5 atomes de carbone, un groupe haloalkyle ayant 1 à 5 atomes de carbone, un groupe haloalcoxy ayant 1 à 5 atomes de carbone, un groupe phényle qui peut être substitué par W, ou similaires ; et W représente un atome d'halogène, CN, un groupe alkyle ayant 1 à 10 atomes de carbone, ou similaires ; et n représente un entier de 1, 2, 3 ou 4.
PCT/JP2007/067726 2006-09-13 2007-09-12 Composition de résist contenant un colorant contenant un générateur de photoacide, et composé de sulfonate d'oxime de type cyclohexadiène WO2008032736A1 (fr)

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JP2006248443A JP2009282052A (ja) 2006-09-13 2006-09-13 光酸発生剤を含む染料含有レジスト組成物及びシクロヘキサジエン系オキシムスルホネート化合物
JP2006-248443 2006-09-13

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JP6123302B2 (ja) * 2013-01-15 2017-05-10 住友ベークライト株式会社 化学増幅型のネガ型フォトレジスト用樹脂組成物、硬化物および電子装置
JP6307989B2 (ja) * 2014-04-02 2018-04-11 住友化学株式会社 塩、酸発生剤、レジスト組成物及びレジストパターンの製造方法

Citations (4)

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Publication number Priority date Publication date Assignee Title
WO1999001429A1 (fr) * 1997-07-01 1999-01-14 Ciba Specialty Chemicals Holding Inc. Nouveaux oximes sulfonates et leur utilisation en tant qu'acides sulfoniques latents
JP2004133393A (ja) * 2002-08-09 2004-04-30 Shin Etsu Chem Co Ltd 化学増幅ポジ型レジスト材料用の光酸発生剤、並びにそれを用いたレジスト材料及びパターン形成方法
WO2006046398A1 (fr) * 2004-10-29 2006-05-04 Nissan Chemical Industries, Ltd. Formules de couches de protection colorées contenant des générateurs photoacides et filtres colorés fabriqués à l'aide desdites couches de protection
JP2006133508A (ja) * 2004-11-05 2006-05-25 Fuji Photo Film Co Ltd 染料含有ネガ型硬化性組成物、カラーフィルタ及びその製造方法

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999001429A1 (fr) * 1997-07-01 1999-01-14 Ciba Specialty Chemicals Holding Inc. Nouveaux oximes sulfonates et leur utilisation en tant qu'acides sulfoniques latents
JP2004133393A (ja) * 2002-08-09 2004-04-30 Shin Etsu Chem Co Ltd 化学増幅ポジ型レジスト材料用の光酸発生剤、並びにそれを用いたレジスト材料及びパターン形成方法
WO2006046398A1 (fr) * 2004-10-29 2006-05-04 Nissan Chemical Industries, Ltd. Formules de couches de protection colorées contenant des générateurs photoacides et filtres colorés fabriqués à l'aide desdites couches de protection
JP2006133508A (ja) * 2004-11-05 2006-05-25 Fuji Photo Film Co Ltd 染料含有ネガ型硬化性組成物、カラーフィルタ及びその製造方法

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KOJI ISHIZU ET AL., POLYMER INTERNATIONAL, vol. 53, 2004, pages 259 - 265
KOJI ISHIZU; AKIHIDE MORI, MACROMOL. RAPID COMMUN., vol. 21, 2000, pages 665 - 668
KOJI ISHIZU; AKIHIDE MORI, POLYMER INTERNATIONAL, vol. 50, 2001, pages 906 - 910
KOJI ISHIZU; TAKESHI SHIBUYA; AKIHIDE MORI, POLYMER INTERNATIONAL, vol. 51, 2002, pages 424 - 428
KOJI ISHIZU; TAKESHI SHIBUYA; SUSUMU KAWAUCHI, MACROMOLECULES, vol. 36, no. 10, 2002, pages 3505 - 3510
KOJI ISHIZU; YOSHIHIRO OHTA; SUSUMU KAWAUCHI, MACROMOLECULES, vol. 35, no. 9, 2002, pages 3781 - 3784
MACROMOL. RAPID COMMUN., vol. 21, 2000, pages 665 - 668
POLYMER INTERNATIONAL, vol. 51, 2002, pages 424 - 428

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