WO2014021100A1 - Composition colorante durcissable et filtre couleur utilisant celle-ci - Google Patents

Composition colorante durcissable et filtre couleur utilisant celle-ci Download PDF

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WO2014021100A1
WO2014021100A1 PCT/JP2013/069346 JP2013069346W WO2014021100A1 WO 2014021100 A1 WO2014021100 A1 WO 2014021100A1 JP 2013069346 W JP2013069346 W JP 2013069346W WO 2014021100 A1 WO2014021100 A1 WO 2014021100A1
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group
general formula
substituent
carbon atoms
colored
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Japanese (ja)
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陽祐 村上
貴規 田口
俊人 空花
藤田　明徳
ゆきえ 渡邊
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富士フイルム株式会社
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3472—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3495—Six-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
    • C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
    • C09B47/0671—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having halogen atoms linked directly to the Pc skeleton
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/10—Obtaining compounds having halogen atoms directly bound to the phthalocyanine skeleton
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/201—Filters in the form of arrays
    • 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
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B3/00—Simple or compound lenses
    • G02B3/0006—Arrays

Definitions

  • the present invention is intended to solve such problems, and a colored curable composition that can form a colored layer pattern that is excellent in spectral characteristics and has high chemical resistance and high heat resistance even when it is thinned.
  • the purpose is to provide.
  • the inventor of the present application studied forming a pattern colored layer by a dry etching process without employing a lithography technique.
  • a high concentration of the colorant inevitably reduces the amount of the additive (curing agent), so that it has chemical resistance and heat resistance (diffusion due to heat). Is a problem. Therefore, as a result of further investigation by the inventors of the present application, by using a halogenated phthalocyanine dye as a colorant in a colored curable composition, even if the colorant concentration is kept high, the chemical resistance and heat resistance are high. It has been found that a colored layer pattern can be formed.
  • Formula (1-1-2) (In the general formula (1-1-2), X 1 represents an oxygen atom or a sulfur atom, and A 11 represents a phenyl group having 1 to 5 substituents R, or a naphthyl having 1 to 7 substituents R.
  • the substituent R is a nitro group, COOR 1 (R 1 is a group represented by the general formula (1-3) or an alkyl group having 1 to 8 carbon atoms), OR 2 (R 2 is carbon An alkyl group having 1 to 8 carbon atoms), a halogen atom, an aryl group, a cyano group, an alkyl group having 1 to 8 carbon atoms, a group represented by any one of general formulas (4) to (6), or a general formula ( Represents a group selected from X).) (In the general formula (4), R 4 is a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, a dialkylamino group which may have a substituent, or a substituent.
  • a plurality of R 11 are each Y 1 may be —O—, —S—, —NR 13 — (R 13 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms), —SO 2 —, or And —C ( ⁇ O) —, R 12 represents a monovalent substituent.
  • General formula (1-3) (In the general formula (1-3), R 3 represents an alkylene group having 1 to 3 carbon atoms, R 4 represents an alkyl group having 1 to 8 carbon atoms, and n represents an integer of 1 to 4)
  • General formula (1-4) In the general formula (1-4), R ′ represents an alkylene group having 1 to 3 carbon atoms, R ′′ represents an alkyl group having 1 to 8 carbon atoms, and n1 represents an integer of 0 to 4) ⁇ 10> A cured film formed by curing the colored curable composition according to any one of ⁇ 1> to ⁇ 9>.
  • (meth) acrylate represents acrylate and methacrylate
  • (meth) acryl represents acryl and methacryl
  • (meth) acryloyl represents acryloyl and methacryloyl
  • the composition of the present invention comprises a halogenated phthalocyanine dye.
  • the halogenated phthalocyanine dye refers to a compound having a phthalocyanine skeleton and having one or more halogen atoms as a substituent. In the present invention, 5 to 15 halogen atoms per molecule are preferable, and 6 to 14 halogen atoms are more preferable. Examples of the halogen atom include a chlorine atom, a fluorine atom, a bromine atom, and an iodine atom.
  • the phthalocyanine dye used in the present invention is preferably a compound represented by the following general formula (1).
  • Z 1 to Z 16 are each a hydrogen atom or a substituent, at least one of the substituents is a halogen atom, and at least one of the other substituents is aromatic.
  • M represents a hydrogen atom (that is, a state in which no central metal M is present), a metal atom, a metal oxide, or a metal halide).
  • the group represented by the general formula (1-2) is more preferably a group represented by the following general formula (1-1-2).
  • Formula (1-1-2) (In the general formula (1-1-2), X 1 represents an oxygen atom or a sulfur atom, and A 11 represents a phenyl group having 1 to 5 substituents R, or a naphthyl having 1 to 7 substituents R.
  • d represents an integer of 0 to 2, and when d is 0 or 1, R 5 is an alkyl group that may have a substituent or an aryl that may have a substituent. And when d is 2, R 5 represents an alkyl group which may have a substituent, an aryl group which may have a substituent, a dialkylamino group which may have a substituent, or a substituent.
  • the bonding position between the naphthyl group and X 1 is not particularly limited, and may be any of the following 1-position (1-naphthyl group) or 2-position (2-naphthyl group).
  • the bonding position of the substituent to the naphthalene ring is not particularly limited.
  • the bonding position of the naphthyl group and X 1 is the 1-position (1-naphthyl group)
  • the bonding position of the substituent to the naphthalene ring is the 2-position, 3-position, 4-position, 5-position, 6
  • the 2nd and 3rd positions are preferable, and the 2nd position is more preferable.
  • the plurality of Rs may be the same or different.
  • R 1 in the COOR 1 is represented by an alkyl group substituted by 1 carbon atoms which may be 1-8 or the following general formula, (1-3) Represents a group.
  • General formula (1-3) (In the general formula (1-3), R 3 represents an alkylene group having 1 to 3 carbon atoms, R 4 represents an alkyl group having 1 to 8 carbon atoms, and n represents an integer of 1 to 4)
  • the alkyloxy group having 1 to 8 carbon atoms which may be present as a substituent of the alkyl group, may be a methoxy group, an ethoxy group, an n-propyloxy group, an iso-propyloxy group, an n-butyloxy group, an iso- Linear chain such as butyloxy group, sec-butyloxy group, t-butyloxy group, n-pentyloxy group, n-hexyloxy group, cyclohexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group And a branched or cyclic alkyloxy group.
  • R 3 in the group represented by the general formula (1-3) is From the viewpoint of the effect on ether solvent solubility, it is 1 to 3 alkylene groups.
  • the alkylene group having 1 to 3 carbon atoms include a methylene group, an ethylene group, an n-propylene group, and an iso-propylene group. Preferably, they are an ethylene group and a propylene group.
  • R 4 in the group represented by the general formula (1-3) is an alkyl group of 1 to 8, more preferably an alkyl group of 1 to 4, from the viewpoint of molecular weight. Examples of the alkyl group having 1 to 8 carbon atoms include those described in the above R 1 column.
  • N in the group represented by the general formula (1-3) is an integer of 1 to 4, and preferably an integer of 1 to 3, from the viewpoint of molecular weight.
  • the alkyl group having 1 to 8 carbon atoms is the same as that described in R 1 of COOR 1 as an example of the substituent R.
  • the preferable range is also synonymous.
  • An alkyl group having 1 to 3 carbon atoms is preferable from the viewpoint of the crystallinity and handleability of the dye.
  • a halogen atom is exemplified, and a fluorine atom, a chlorine atom, a bromine atom and an iodine atom are preferable, and a fluorine atom or a chlorine atom is more preferable.
  • dialkylamino group having 2 to 20 carbon atoms More preferred is a dialkylamino group having 2 to 20 carbon atoms, a diarylamino group having 12 to 20 carbon atoms in total, or an alkylarylamino group having 7 to 20 carbon atoms in total, and a diarylamino group having 12 to 20 carbon atoms in total or Dialkylamino groups of primes 2-20 is particularly preferred.
  • R 5 is preferably a dialkylamino group having 2 to 20 carbon atoms, a diarylamino group having 12 to 20 carbon atoms, or an alkylarylamino group having 7 to 20 carbon atoms when d is 2.
  • the alkyl moiety and the aryl moiety may further have a substituent, and examples of the substituent include a substituent T described later.
  • An alkoxy group, an aryl group, an aryloxy group, an alkoxycarbonyl group, an alkylthio group, and an arylthio group. Or a halogen atom etc. are preferable, an alkoxy group is more preferable, and a methoxy group or an ethoxy group is further more preferable.
  • the aspect which does not have a substituent is also preferable.
  • R 6 and R 7 are each an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkylcarbonyl group which may have a substituent, An arylcarbonyl group which may have a substituent, an alkylsulfonyl group which may have a substituent, an arylsulfonyl group which may have a substituent, an alkyl group having 1 to 20 carbon atoms, a carbon number of 6 An aryl group having ⁇ 20, an alkylcarbonyl group having 2 to 20 carbon atoms, an arylcarbonyl group having 7 to 20 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms, and an arylsulfonyl group having 6 to 20 carbon atoms are preferable.
  • alkylcarbonyl group having 2 to 20 carbon atoms, an arylcarbonyl group having 7 to 20 carbon atoms, an alkylsulfonyl group having 1 to 20 carbon atoms, and an arylsulfonyl group having 6 to 20 carbon atoms are more preferable.
  • the alkyl moiety and the aryl moiety may further have a substituent, and examples of the substituent include a substituent T described later.
  • an alkoxy group is more preferable, and a methoxy group or an ethoxy group is further more preferable.
  • the aspect which does not have a substituent is also preferable. Examples of the alkyl group and the like which may have a substituent will be described later.
  • alkyl group that may have a substituent in the above general formula are shown below.
  • alkyl group which may have a substituent include a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a 2-ethylhexyl group, a dodecyl group, Hexadecyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, 1-norbornyl group, 1-adamantyl group, phenoxyethyl group, benzyl group, phenylethyl group, N-butylaminosulfonylpropyl group, N-butylaminocarbonylmethyl group, N, N-dibutylaminosulfon
  • methyl group ethyl group, propyl group, tert-butyl group, phenoxyethyl.
  • benzyl group phenylethyl group, N-butylaminosulfonylpropyl group, N-butylaminocarbonylmethyl group, N, N-dibutylaminosulfonylpropyl group and ethoxyethoxyethyl group.
  • aryl groups which may have a substituent in the general formulas (4) to (6) are shown below.
  • Such aryl groups include phenyl, 2-chlorophenyl, 2-methoxyphenyl, 4-butoxycarbonylphenyl, 4-N, N-dibutylaminocarbonylphenyl, 4-N-butylaminosulfonylphenyl 4-N, N-dibutylaminosulfonylphenyl group, more preferably phenyl group, 4-butoxycarbonylphenyl group, 4-N, N-dibutylaminocarbonylphenyl group, 4-N-butylaminosulfonylphenyl group.
  • dialkylamino group which may have a substituent in the general formulas (4) to (6) are shown below.
  • Examples of such a dialkylamino group include N, N-dimethylamino group, N, N-dibutylamino group, N, N-di (2-ethylhexyl) amino group, N-methyl-N-benzylamino group, N, N-di (2-ethoxyethyl) amino group and N, N-di (2-hydroxyethyl) amino group can be mentioned.
  • diarylamino group which may have a substituent in the general formulas (4) to (6) are shown below.
  • Examples of such a diarylamino group include an N, N-diphenylamino group, an N, N-di (4-methoxyphenyl) amino group, and an N, N-di (4-acylphenyl) amino group.
  • alkylcarbonyl group which may have a substituent in the general formulas (4) to (6) are shown below.
  • Examples of such an alkylcarbonyl group include an acetyl group, a propylcarbonyl group, a heptyl-3-carbonyl group, a 2-ethylhexyloxymethylcarbonyl group, a phenoxymethylcarbonyl group, and a 2-ethylhexyloxycarbonylmethylcarbonyl group.
  • alkylsulfonyl group which may have a substituent in the general formulas (4) to (6) are shown below.
  • alkylsulfonyl group examples include a methanesulfonyl group, an octanesulfonyl group, a dodecylsulfonyl group, a benzylsulfonyl group, and a phenoxypropylsulfonyl group.
  • arylsulfonyl group which may have a substituent in the general formulas (4) to (6) are shown below.
  • Examples of such an arylsulfonyl group include a phenylsulfonyl group, a 2-methoxyphenylsulfonyl group, and a 4-ethoxycarbonylphenylsulfonyl group.
  • alkylsulfonylamino group which may have a substituent in the general formulas (4) to (6) are shown below.
  • alkylsulfonylamino group examples include a methylsulfonylamino group, a butylsulfonylamino group, a hydroxypropylsulfonylamino group, a 2-ethylhexylsulfonylamino group, an n-octylsulfonylamino group, a phenoxyethylsulfonylamino group, and an allylsulfonylamino group. Is mentioned.
  • examples of the vinylsulfonylamino group which may have a substituent include a vinylsulfonylamino group and a 1-methylvinylsulfonylamino group.
  • the arylsulfonylamino group which may have a substituent includes a phenylsulfonylamino group, a p-methoxyphenylsulfonylamino group, a p-ethoxycarbonylsulfonylamino group, and the like. Is mentioned.
  • the alkylcarbonylamino group which may have a substituent is a methylcarbonylamino group, a 2-ethylhexanoylamino group, an n-heptylcarbonylamino group, an ethoxyethoxy group.
  • Examples include a methylcarbonylamino group.
  • examples of the arylcarbonylamino group which may have a substituent include a benzoylamino group, a 2-methoxybenzoylamino group, and a 4-vinylbenzoylamino group.
  • substituent When the above-described substituent is a substitutable group, it may be further substituted with any of the above-described groups. In addition, when it has two or more substituents, those substituents may be the same or different.
  • R 11 represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom.
  • n1 represents an integer of 1 to 3, more preferably 1 or 2. When n1 is 2 or 3, the plurality of R 11 may be the same or different.
  • Y 1 represents —O—, —S—, —NR 13 —, —SO 2 —, or —C ( ⁇ O) —, and represents —O—, —SO 2 —, or —C ( ⁇ O).
  • -Is preferred, and -O- or -C ( O)-is more preferred.
  • R 12 represents a monovalent substituent, and examples of the substituent include the above-described substituent T.
  • the substituent T may be further substituted with the substituent T.
  • R 12 is preferably an alkyl group which may have a substituent, an acyl group which may have a substituent, a sulfonyl group which may have a substituent, an alkoxy group which may have a substituent, Or an alkylamino group which may have a substituent, more preferably an alkyl group having 1 to 12 carbon atoms which may have a substituent, and 1 to 12 carbon atoms which may have a substituent. And an alkylamino group having 1 to 12 carbon atoms which may have a substituent.
  • the mass of the R 12 portion per molecule is preferably 200 to 2500, and more preferably 250 to 1500.
  • R 13 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • R ′ is an alkylene group having 1 to 3 carbon atoms from the viewpoint of ether solubility and molecular weight.
  • alkylene group having 1 to 3 carbon atoms include a methylene group, an ethylene group, an n-propylene group, and an iso-propylene group.
  • they are an ethylene group and a propylene group.
  • R ′′ is an alkyl group having 1 to 8 carbon atoms, preferably an alkyl group having 1 to 2 carbon atoms from the viewpoint of ether solubility and molecular weight, and the alkyl group having 1 to 8 carbon atoms may be represented by the general formula (1 -3) has the same meaning as R 3 , and the preferred range is also the same.
  • n1 is an integer of 0 to 4, more preferably an integer of 1 to 2, from the viewpoint of ether solubility and molecular weight.
  • M which is the central part of the general formula (1).
  • M represents two hydrogen atoms (that is, a state in which the central metal M does not exist), a metal atom, a metal oxide, or a metal halide.
  • the metal atom include iron, magnesium, nickel, cobalt, copper, palladium, zinc, vanadium, titanium, indium, and tin.
  • the metal oxide include titanyl and vanadyl.
  • the metal halide include aluminum chloride, indium chloride, germanium chloride, tin (II) chloride, tin (IV) chloride, and silicon chloride.
  • the central metal is zinc or copper because of high heat resistance.
  • the central metal is zinc because the transmittance in the vicinity of 520 nm to 545 nm, which is a green wavelength, is higher than that of copper, and the luminance can be improved when a color filter is formed.
  • it is particularly preferable because it has high solvent solubility in general-purpose solvents such as acetone, methanol, and methyl cellosolve, and has high solubility in resins and high contrast.
  • the compound represented by the general formula (1) is more preferably represented by the following general formula (1-1).
  • General formula (1-1) (In the general formula (1-1), Z 1 to Z 16 are each a hydrogen atom, a halogen atom, a group represented by the general formula (1-1-2), or a general formula (1-3).
  • a group represented by the general formula (1-4), and 1 to 8 of Z 1 to Z 16 are groups represented by the general formula (1-1-2)
  • Represents a hydrogen atom that is, a state in which no central metal M exists
  • a metal atom that is, a state in which no central metal M exists
  • a metal atom that is, a state in which no central metal M exists
  • a metal atom that is, a state in which no central metal M exists
  • a metal atom that is, a state in which no central
  • the general formula (1-1-2), the general formula (1-3), and the general formula (1-4) in the general formula (1-1) are represented by the general formula (1-1) described in the general formula (1).
  • Z 1 to Z 16 in the general formula (1-1) are more preferably in the same range as Z 1 to Z 16 in the general formula (1).
  • M in the general formula (1-1) has the same meaning as M in the general formula (1), and a preferred range is also the same.
  • Z 1 to Z 16 in the general formula (1-1) preferably have a group represented by the general formula (1-1-2) or the general formula (1-4).
  • a 11 in the general formula (1-1-2) is a phenyl group having 1 to 5 substituents R, and the substituent R is represented by COOR 1 (R 1 is represented by the general formula (1-3).
  • R 1 is represented by the general formula (1-3).
  • M represents two hydrogen atoms, a metal atom, a metal oxide, or a metal halide.
  • Formula (1-5-1) (In the general formula (1-5-1), L 1 represents a divalent linking group, Ar represents an arylene group, and A represents a group represented by the following general formula (1-5-2). (* Represents the site of binding to the phthalocyanine ring.)
  • Formula (1-5-2) (In the general formula (1-5-2), L 2 represents a single bond or a divalent linking group, R 5 to R 7 each represents a hydrogen atom or a monovalent substituent, and * represents a general formula. (Represents the site for binding to Ar in (1-5-1).)
  • L 1 represents a divalent linking group.
  • L 1 represents one of —O—, —S—, —C ( ⁇ O) —, —CH 2 —, —C ( ⁇ S) —, —NR A —, —SO—, —SO 2 —, or A divalent linking group consisting of two or more combinations is preferred, and one or a combination of two or more of —O—, —S—, —C ( ⁇ O) —, —CH 2 —, —SO 2 — is preferred.
  • —O— or —S— is more preferable, and —O— is particularly preferable.
  • R A represents a hydrogen atom, an alkyl group or an aryl group
  • the alkyl group is an alkyl group having 1 to 10 carbon atoms (methyl group, ethyl group, hexyl group, cyclohexyl group, etc.)
  • the aryl group is a carbon atom
  • An aryl group of 6 to 10 phenyl group, naphthyl group, etc.
  • R A is preferably a hydrogen atom, a methyl group or an ethyl group, more preferably a hydrogen atom or a methyl group, and even more preferably a hydrogen atom.
  • Ar represents an arylene group.
  • the arylene group here refers to a so-called aromatic ring group and does not include a heterocyclic group.
  • Ar is preferably a phenylene group or a naphthylene group, more preferably a phenylene group or a naphthylene group, and even more preferably a phenylene group.
  • the general formula (1-5-2) preferably has an acrylate structure or a methacrylate structure.
  • L 2 preferably has a C ( ⁇ O) O— structure on the double bond side.
  • R B has the same meaning as R A described above, and the preferred range is also the same.
  • R 5 to R 7 each represents a hydrogen atom or a monovalent substituent.
  • the monovalent substituent include the above-described substituent T, and an alkyl group is preferable, and an alkyl group having 1 to 10 carbon atoms (methyl group, ethyl group, hexyl group, cyclohexyl group) and the like are more preferable.
  • R 5 to R 7 are more preferably a hydrogen atom or a methyl group
  • R 6 and R 7 are particularly preferably a hydrogen atom
  • R 5 is particularly preferably a hydrogen atom or a methyl group.
  • the general formula (1-5-2) is preferably represented by a * -L 2A- (meth) acryloyloxy group.
  • L 2A has the same meaning as the above divalent linking group, and is one or more of —O—, —C ( ⁇ O) —, —CH 2 —, —CH (OH) —, —NR B —. It is more preferable that the group is a combination of the above.
  • Pc represents a phthalocyanine nucleus
  • Zn represents a central metal
  • a substituent substituted at the ⁇ -position immediately after Pc and a substituent substituted at the ⁇ -position after the substituent substituted at the ⁇ -position.
  • x and y are positive numbers whose number of substituents is 0 or more.
  • the phthalocyanine compound is a mixture having different substitution positions and substitution numbers, it is difficult to uniquely describe it as a structural formula. Further, the number of substitutions shown in the following table is a value obtained by approximating the average value of the number of substituents in the mixture, and may be a small number.
  • the method for producing the phthalocyanine compound used in the present invention is not particularly limited, and a conventionally known method can be used. A method of cyclizing a phthalonitrile compound and a metal salt, preferably in a molten state or in an organic solvent, can be used particularly preferably.
  • a method of cyclizing a phthalonitrile compound and a metal salt, preferably in a molten state or in an organic solvent can be used particularly preferably.
  • preferred embodiments of the method for producing a phthalocyanine compound will be described. However, the present invention is not limited to the following preferred embodiments.
  • a phthalocyanine compound can be produced by cyclization reaction with one selected.
  • Z 1 to Z 16 are defined by the structure of the desired phthalocyanine compound (1).
  • Z 1 to Z 16 are the same as the definitions of Z 1 to Z 16 in the above formula (1), respectively, and thus description thereof is omitted here. To do.
  • the cyclization reaction can be synthesized by a conventionally known method such as the method described in JP-A No. 64-45474.
  • the cyclization reaction may be performed by melting one kind selected from the group consisting of the phthalonitrile compounds of formulas (I) to (IV) and a metal, a metal oxide, a metal carbonyl, a metal halide, and an organic acid metal in a molten state or organic It is preferable to react in a solvent.
  • the metal, metal oxide, metal carbonyl, metal halide, and organic acid metal that can be used at this time are those corresponding to the central portion of the phthalocyanine compound obtained after the reaction (M in the general formula (1)). If there is, there is no particular limitation.
  • metals such as iron, copper, zinc, vanadium, titanium, indium, and tin listed in the item M in the general formula (1), metal halide compounds such as chloride, bromide, and iodide of the metal, Examples thereof include metal oxides such as vanadium oxide, titanium oxide and copper oxide, organic acid metals such as acetate, complex compounds such as acetylacetonate, and metal carbonyls such as carbonyl iron.
  • metals such as iron, copper, zinc, vanadium, titanium, indium, magnesium, and tin
  • metal halides such as chloride, bromide, and iodide of the metal, such as vanadium chloride, titanium chloride, and chloride Copper, zinc chloride, cobalt chloride, nickel chloride, iron chloride, indium chloride, aluminum chloride, tin chloride, gallium chloride, germanium chloride, magnesium chloride, copper iodide, zinc iodide, cobalt iodide, indium iodide, iodide
  • vanadium monoxide, vanadium trioxide, vanadium tetroxide vanadium pentoxide, titanium dioxide, iron monoxide, three Iron dioxide, iron trioxide, manganese oxide, nickel monoxide, cobalt monoxide,
  • metals metal oxides and metal halides
  • metal halides metal halides
  • vanadium iodide copper iodide and zinc iodide
  • iodine copper iodide and zinc iodide
  • Copper iodide and zinc iodide most preferably zinc iodide.
  • zinc iodide the central metal is zinc.
  • metal halides it is preferable to use iodide because it has excellent solubility in solvents and resins, and the spectrum of the resulting phthalocyanine compound is sharp and easily fits within the desired wavelength range of 640 to 750 nm. is there.
  • the detailed mechanism of sharpening the spectrum when using iodide during the cyclization reaction is unknown, but when iodide is used, the iodine remaining in the phthalocyanine compound after the reaction may not interact with the phthalocyanine compound. It is presumed that iodine is present between the layers of the phthalocyanine compound due to the action. However, the mechanism is not limited to the above mechanism. In order to obtain the same effect as when metal iodide is used for the cyclization reaction, the obtained phthalocyanine compound may be treated with iodine.
  • 1-chloronaphthalene, 1-methylnaphthalene, 1-octanol, dichlorobenzene and benzonitrile are preferably used, and more preferably 1-octanol, dichlorobenzene and benzonitrile are used.
  • These solvents may be used alone or in combination of two or more.
  • the reaction conditions for the phthalonitrile compound of formulas (I) to (IV) and the metal compound in the above embodiment are not particularly limited as long as the reaction proceeds.
  • the total amount of the phthalonitrile compounds of the above formulas (I) to (IV) is 1 to 500 parts by weight, preferably 10 to 350 parts by weight, and the metal compound is used with respect to 4 moles of the phthalonitrile compound. , Preferably 0.8 to 2.0 mol, more preferably 0.8 to 1.5 mol.
  • the cyclization is not particularly limited, but the reaction is preferably performed at a reaction temperature of 30 to 250 ° C., more preferably 80 to 200 ° C.
  • the reaction time is not particularly limited, but is preferably 3 to 20 hours.
  • a phthalocyanine compound that can be used in the next step can be efficiently and highly purified by filtration, washing, and drying according to a conventionally known method for synthesizing phthalocyanine compounds.
  • the starting phthalonitrile compounds of formulas (I) to (IV) can be synthesized by a conventionally known method, or commercially available products can also be used.
  • L 1 represents a single bond or a divalent linking group.
  • the divalent linking group includes a substituted or unsubstituted alkylene group having 1 to 30 carbon atoms (eg, methylene group, ethylene group, trimethylene group, propylene group, butylene).
  • L 3 represents a single bond or a divalent linking group.
  • DyeIII represents a structure containing a halogenated phthalocyanine skeleton.
  • m represents 0 or 1;
  • n-valent linking group where n is 3 or more is a substituted or unsubstituted arylene group (1,3,5-phenylene group, 1,2,4-phenylene group, 1,4,5,8-naphthalene group, etc.) And a linking group formed by substituting the divalent linking group with a heterocyclic linking group (for example, 1,3,5-triazine group, etc.), an alkylene linking group or the like as a central mother nucleus.
  • a heterocyclic linking group for example, 1,3,5-triazine group, etc.
  • the polymerizable group amount of the halogenated phthalocyanine multimer is preferably 0.1 mmol to 2.0 mmol, more preferably 0.2 mmol to 1.5 mmol, and more preferably 0.3 mmol to 1. Particularly preferred is 0 mmol.
  • the weight average molecular weight of the halogenated phthalocyanine multimer is preferably 2,000 to 20,000, more preferably 3,000 to 15,000, and most preferably 4,000 to 10,000. preferable.
  • the weight average molecular weight / number average molecular weight ratio of the halogenated phthalocyanine multimer is preferably 1.0 to 3.0, more preferably 1.6 to 2.5, and more preferably 1.6 to 2 0.0 is most preferred.
  • the weight average molecular weight and degree of dispersion of the polymer are defined as polystyrene conversion values by GPC measurement.
  • Examples of the pigment that can be preferably used in the present invention include the following. However, the present invention is not limited to these.
  • the colorant when the colorant is a dye, a colored curable composition in a state of being uniformly dissolved in the composition can be obtained.
  • a well-known dye can be used for conventional color filters.
  • Examples of the chemical structure include azo series (for example, CI solvent yellow 162) and methine series (CI solvent yellow 93).
  • CI solvent yellow 162 As the methine dye, a monomethine dye is preferable, and a monomethine dye represented by the following general formula (5) is more preferable.
  • the yellow dye used in the present invention is particularly preferably an azo dye and / or a methine dye.
  • the polymer dispersant is adsorbed on the surface of the pigment and acts to prevent reaggregation. Therefore, a terminal-modified polymer, a graft polymer and a block polymer having an anchor site to the pigment surface can be mentioned as preferred structures.
  • the pigment derivative has an effect of promoting the adsorption of the polymer dispersant by modifying the pigment surface.
  • a dispersant described in paragraphs 0028 to 0124 of JP2011-070156A and a dispersant described in JP2007-277514A are preferably used, and the contents thereof are incorporated in the present specification.
  • a pigment When a pigment is contained as a colorant, it is preferable to further contain a pigment derivative in order to increase the adsorptivity of the dispersion resin to the pigment.
  • the pigment derivative is a compound having a structure in which a part of an organic pigment is substituted with an acidic group, a basic group or a phthalimidomethyl group.
  • the pigment derivative preferably contains a pigment derivative having an acidic group or a basic group from the viewpoint of dispersibility and dispersion stability.
  • Rp1 is particularly preferably a methyl group or a phenyl group, and most preferably a methyl group.
  • Rp2 is preferably a hydrogen atom or a halogen atom, and most preferably a hydrogen atom or a chlorine atom.
  • R EP1 to R EP3 each represent a hydrogen atom, a halogen atom, or an alkyl group, and the alkyl group may have a cyclic structure, and has a substituent. May be. R EP1 and R EP2 and R EP2 and R EP3 may be bonded to each other to form a ring structure.
  • the epoxy compound used in the present invention is also preferably an oligomer or polymer having an epoxy group in the side chain.
  • examples of such compounds include bisphenol A type epoxy resins, bisphenol F type epoxy resins, phenol novolac type epoxy resins, and cresol novolac type epoxy resins. And aliphatic epoxy resins. These compounds may be used as commercial products or can be obtained by introducing an epoxy group into the side chain of the polymer.
  • ADEKA RESIN EP-4000S, EP-4003S, EP-4010S, EP-4010S, EP-4011S (above, manufactured by ADEKA Corporation), NC-2000, NC-3000, NC-7300, XD-1000, EPPN-501, EPPN-502 (above, manufactured by ADEKA Corporation), JER1031S (manufactured by Japan Epoxy Resin Co., Ltd.) and the like.
  • the introduction reaction includes tertiary amines such as triethylamine and benzylmethylamine, quaternary ammonium salts such as dodecyltrimethylammonium chloride, tetramethylammonium chloride, tetraethylammonium chloride, pyridine,
  • the reaction can be carried out in an organic solvent at a reaction temperature of 50 to 150 ° C. for several to several tens of hours using triphenylphosphine as a catalyst.
  • the amount of the alicyclic epoxy unsaturated compound introduced is preferably controlled so that the acid value of the obtained polymer is in a range satisfying 5 to 200 KOH ⁇ mg / g.
  • the molecular weight is preferably in the range of 500 to 5000000, more preferably 1000 to 500000 on a weight average.
  • the epoxy unsaturated compound those having a glycidyl group as an epoxy group such as glycidyl (meth) acrylate and allyl glycidyl ether can be used, but preferred are unsaturated compounds having an alicyclic epoxy group. Examples of such compounds include the following compounds.
  • thermosetting compound used in the present invention compounds having the following N-hydroxymethyl group, N-alkoxymethyl group, or N-acyloxymethyl group are also preferable.
  • Such a compound is usually provided as a melamine compound or a urea compound.
  • the compound having an N-hydroxymethyl group, an N-alkoxymethyl group, or an N-acyloxymethyl group has two or more (more preferably 2 to 8) partial structures represented by the following general formula (CLNM-1). ) Is preferred.
  • R NM1 represents a hydrogen atom, an alkyl group, a cycloalkyl group, or an oxoalkyl group.
  • the alkyl group represented by R NM1 is preferably a linear or branched alkyl group having 1 to 6 carbon atoms.
  • the cycloalkyl group of R NM1 is preferably a cycloalkyl group having 5 to 6 carbon atoms.
  • the oxoalkyl group of R NM1 is preferably an oxoalkyl group having 3 to 6 carbon atoms, and examples thereof include a ⁇ -oxopropyl group, a ⁇ -oxobutyl group, a ⁇ -oxopentyl group, and a ⁇ -oxohexyl group. it can.
  • R NM1 are respectively those in formula (CLNM-1) at, the same as R NM1.
  • R NM2 represents a hydrogen atom, an alkyl group (preferably having 1 to 6 carbon atoms), or a cycloalkyl group (preferably having 5 to 6 carbon atoms).
  • urea compound represented by the general formula (CLNM-2) include, for example, N, N-di (methoxymethyl) urea, N, N-di (ethoxymethyl) urea, N, N-di (propoxy).
  • Methyl) urea N, N-di (isopropoxymethyl) urea, N, N-di (butoxymethyl) urea, N, N-di (t-butoxymethyl) urea, N, N-di (cyclohexyloxymethyl) Examples include urea, N, N-di (cyclopentyloxymethyl) urea, N, N-di (adamantyloxymethyl) urea, N, N-di (norbornyloxymethyl) urea and the like.
  • R NM1 are respectively those in formula (CLNM-1) at, the same as R NM1.
  • R NM3 represents a hydrogen atom, a hydroxyl group, a linear or branched alkyl group (preferably having 1 to 6 carbon atoms), a cycloalkyl group (preferably having 5 to 6 carbon atoms), an oxoalkyl group (having 1 to 6 carbon atoms). 6 is preferred), an alkoxy group (preferably having 1 to 6 carbon atoms) or an oxoalkoxy group (preferably having 1 to 6 carbon atoms).
  • G represents a single bond, an oxygen atom, a sulfur atom, an alkylene group (preferably having 1 to 3 carbon atoms) or a carbonyl group. More specific examples include a methylene group, an ethylene group, a propylene group, a 1-methylethylene group, a hydroxymethylene group, a cyanomethylene group, and the like.
  • alkylene urea compound represented by the general formula (CLNM-3) include, for example, N, N-di (methoxymethyl) -4,5-di (methoxymethyl) ethylene urea, N, N-di ( Ethoxymethyl) -4,5-di (ethoxymethyl) ethyleneurea, N, N-di (propoxymethyl) -4,5-di (propoxymethyl) ethyleneurea, N, N-di (isopropoxymethyl) -4 , 5-Di (isopropoxymethyl) ethyleneurea, N, N-di (butoxymethyl) -4,5-di (butoxymethyl) ethyleneurea, N, N-di (t-butoxymethyl) -4,5- Di (t-butoxymethyl) ethyleneurea, N, N-di (cyclohexyloxymethyl) -4,5-di (cyclohexyloxymethyl) ethyleneurea, N, N-di (cyclo Nthyloxymethyl)
  • R NM1 are respectively those in formula (CLNM-1) at, the same as R NM1.
  • R NM4 represents a hydrogen atom, a hydroxyl group, an alkyl group, a cycloalkyl group, or an alkoxy group, respectively.
  • R NM4 alkyl group preferably having 1 to 6 carbon atoms
  • cycloalkyl group preferably having 5 to 6 carbon atoms
  • alkoxy group preferably having 1 to 6 carbon atoms
  • Examples include an ethyl group, a butyl group, a cyclopentyl group, a cyclohexyl group, a methoxy group, an ethoxy group, and a butoxy group.
  • R NM1 are respectively those in formula (CLNM-1) at, the same as R NM1.
  • R NM5 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an atomic group represented by the following general formula (CLNM-5 ′).
  • R NM6 represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an atomic group represented by the following general formula (CLNM-5 ′′).
  • R NM1 are those in formula (CLNM-1) at, the same as R NM1.
  • R NM1 is in formula (CLNM-1), is similar to the R NM1, R NM5 is in formula (CLNM-5) R It is the same as NM5 .
  • Alkyl group R NM5 and R NM6 (preferably having 1 to 6 carbon atoms), a cycloalkyl group (preferably 5 to 6 carbon atoms), aryl group (preferably 6 to 10 carbon atoms), and more specifically, Examples thereof include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, a pentyl group, a cyclopentyl group, a hexyl group, a cyclohexyl group, a phenyl group, and a naphthyl group.
  • Examples of the melamine compound represented by the general formula (CLNM-5) include N, N, N, N, N, N-hexa (methoxymethyl) melamine, N, N, N, N, N-hexa (Ethoxymethyl) melamine, N, N, N, N, N-hexa (propoxymethyl) melamine, N, N, N, N, N-hexa (isopropoxymethyl) melamine, N, N, N , N, N-hexa (butoxymethyl) melamine, N, N, N, N, N-hexa (t-butoxymethyl) melamine, N, N, N, N, N, N-hexa (cyclohexyl) Oxymethyl) melamine, N, N, N, N, N, N, N-hexa (cyclopentyloxymethyl) melamine, N, N, N, N, N, N-hexa (adamantyloxymethyl) melamine
  • the groups represented by R NM1 to R NM6 in the general formulas (CLNM-1) to (CLNM-5) may further have a substituent.
  • substituents that R NM1 to R NM6 may have include, for example, a halogen atom, a hydroxyl group, a nitro group, a cyano group, a carboxyl group, a cycloalkyl group (preferably having 3 to 20 carbon atoms), an aryl group (preferably 6 to 14 carbon atoms), alkoxy group (preferably 1 to 20 carbon atoms), cycloalkoxy group (preferably 3 to 20 carbon atoms), acyl group (preferably 2 to 20 carbon atoms), acyloxy group (preferably carbon atoms) 2 to 20).
  • the phenol compound contains 3 to 5 benzene rings in the molecule, and further has two or more hydroxymethyl groups or alkoxymethyl groups, and the hydroxymethyl group or alkoxymethyl group is attached to at least one of the benzene rings. Mention may be made of phenolic compounds which are concentrated or distributed and combined. As the alkoxymethyl group bonded to the benzene ring, those having 6 or less carbon atoms are preferable. Specifically, methoxymethyl group, ethoxymethyl group, n-propoxymethyl group, i-propoxymethyl group, n-butoxymethyl group, i-butoxymethyl group, sec-butoxymethyl group, and t-butoxymethyl group are preferable.
  • thermosetting compound is more preferably a phenol compound having two or more benzene rings in the molecule, and is preferably a phenol compound containing no nitrogen atom.
  • the thermosetting compound is preferably a phenol compound having 2 to 8 thermosetting functional groups per molecule, and more preferably 3 to 6 thermosetting functional groups.
  • L 1 to L 8 represent a thermosetting functional group such as an alkoxymethyl group, and may be the same or different, and the thermosetting functional group is preferably a hydroxymethyl group, a methoxymethyl group or An ethoxymethyl group is shown.
  • thermosetting compound may be used alone or in combination of two or more.
  • the total content of the thermosetting compound in the composition of the present invention varies depending on the material, but is preferably 5 to 40% by mass, preferably 7 to 35%, based on the total solid content (mass) of the colored curable composition. % By mass is more preferable, and 10 to 30% by mass is particularly preferable. In this invention, the effect that the cured film excellent in chemical-resistance can be obtained by setting it as the compounding quantity of such a thermosetting compound is acquired.
  • the colored curable composition of the present invention contains a solvent (usually an organic solvent) that dissolves at least the halogenated phthalocyanine dye and the thermosetting compound.
  • a solvent usually an organic solvent
  • the solvent dissolves the halogenated phthalocyanine dye and the thermosetting compound means that the solvent (25 ° C., 100 g) in the colored curable composition of the present invention is a halogenated phthalocyanine in the composition. It means that 1 g or more of the dye and / or thermosetting compound is dissolved.
  • organic solvents examples include esters such as ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl lactate, and ethyl lactate.
  • Alkyl oxyacetates eg, methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate (eg, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate)
  • alkyl 3-oxypropionate Esters eg, methyl 3-oxypropionate, ethyl 3-oxypropionate, etc.
  • 2- Xylpropionic acid alkyl esters eg, methyl 2-oxypropionate, ethyl 2-oxypropionate, propyl 2-oxypropionate, etc.
  • solvents are preferably mixed in two or more types from the viewpoint of improving the coated surface.
  • It is a mixed solution composed of two or more selected from carbitol acetate, butyl carbitol acetate, propylene glycol methyl ether, and propylene glycol methyl ether acetate.
  • the colored curable composition of the present invention has various additives as required, for example, surfactants, acid anhydrides, curing agents, curing catalysts, fillers, adhesion promoters, as long as the effects of the present invention are not impaired.
  • An agent, an antioxidant, an ultraviolet absorber, an aggregation inhibitor and the like can be blended.
  • the amount of the photopolymerizable compound is preferably 1% by mass or less, more preferably 0.5% by mass or less, based on the total solid content. Is more preferable.
  • Various colored surfactants may be added to the colored curable composition of the present invention from the viewpoint of further improving coatability.
  • the surfactant various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone-based surfactant can be used.
  • the colored curable composition of the present invention contains a fluorosurfactant, so that the liquid properties (particularly fluidity) when prepared as a coating liquid are further improved, so that the coating thickness is uniform.
  • the liquid-saving property can be further improved. That is, when a film is formed using a coating liquid to which a colored curable composition containing a fluorosurfactant is applied, by reducing the interfacial tension between the coated surface and the coating liquid, The wettability is improved, and the coating property to the coated surface is improved. For this reason, even when a thin film of about several ⁇ m is formed with a small amount of liquid, it is effective in that it is possible to more suitably form a film having a uniform thickness with small thickness unevenness.
  • the fluorine content in the fluorosurfactant is preferably 3% by mass to 40% by mass, more preferably 5% by mass to 30% by mass, and particularly preferably 7% by mass to 25% by mass.
  • a fluorine-based surfactant having a fluorine content in this range is effective in terms of uniformity of coating film thickness and liquid-saving properties, and has good solubility in a colored curable composition.
  • fluorosurfactant examples include MegaFuck F781 (manufactured by DIC Corporation).
  • the colored curable composition may or may not contain a surfactant, but when it is contained, the addition amount of the surfactant is 0.001% by mass relative to the total mass of the colored curable composition.
  • the content is preferably -2.0% by mass, more preferably 0.005% -1.0% by mass.
  • the solid content acid value of the polymer compound is 80 mgKOH / g or less.
  • the colored curable composition of the present invention may contain an acid anhydride.
  • an acid anhydride By containing an acid anhydride, it is possible to improve the crosslinkability of the thermosetting compound, particularly the epoxy compound, by thermosetting.
  • the acid anhydride examples include phthalic anhydride, nadic anhydride, maleic anhydride, succinic anhydride, and the like. Among these, phthalic anhydride is preferable because the acid anhydride has little influence on pigment dispersion.
  • An amine compound is generally used as an epoxy curing agent, but has advantages such as a relatively long pot life.
  • the content of the acid anhydride in the colored curable composition is preferably in the range of 10 to 40% by mass, and in the range of 15 to 30% by mass with respect to the content of the thermosetting compound (particularly the epoxy compound). More preferred.
  • the content of the acid anhydride is 10% by mass or more, the crosslinking density of the thermosetting compound, particularly epoxy, can be improved, and the mechanical strength can be increased. Curing components are suppressed, which is advantageous for increasing the concentration of the coloring material.
  • thermosetting compound When using an epoxy resin as the thermosetting compound, it is preferable to add a curing agent.
  • curing agents for epoxy resins, and their properties, pot life with resin and curing agent mixture, viscosity, curing temperature, curing time, heat generation, etc. vary greatly depending on the type of curing agent used.
  • An appropriate curing agent must be selected according to the purpose of use, use conditions, working conditions, and the like. The curing agent is explained in detail in Chapter 5 of Hiroshi Kakiuchi “Epoxy resin (Shojodo)”. Examples of curing agents are shown below.
  • Those that act catalytically include tertiary amines, boron trifluoride-amine complexes, those that react stoichiometrically with functional groups of epoxy resins, polyamines, acid anhydrides, etc .;
  • Examples include diethylenetriamine, polyamide resin, and medium temperature curing examples such as diethylaminopropylamine and tris (dimethylaminomethyl) phenol;
  • examples of high temperature curing include phthalic anhydride and metaphenylenediamine.
  • the pore size of the filter is not particularly limited, but is, for example, about 0.01 to 20.0 ⁇ m, preferably about 0.01 to 5 ⁇ m, and more preferably about 0.01 to 2.0 ⁇ m.
  • the pore size of the filter can refer to the nominal value of the filter manufacturer.
  • a commercially available filter for example, it can be selected from various filters provided by Nippon Pole Co., Ltd., Advantech Toyo Co., Ltd., Japan Entegris Co., Ltd. (former Nihon Microlith Co., Ltd.), Kitz Micro Filter Co., Ltd. .
  • the colored curable composition of the present invention is cured and preferably used as a cured film.
  • the layer obtained by curing the colored curable composition of the present invention can be preferably used as a colored layer of a color filter. In particular, it can be preferably used as a colored curable composition for dry etching.
  • the first colored layer exposes the organic solvent in the second or third colored radiation-sensitive composition and the second or third colored radiation-sensitive layer formed by the second or third colored radiation-sensitive composition,
  • the color component in the first colored layer may be eluted into the solvent or developer, or the color component in the second or third colored radiation-sensitive composition is May be mixed into the first colored layer It can be suppressed.
  • An insulating film 47 such as SiO 2 or SiO 2 / SiN / SiO 2 is provided on the P well 41, the photodiode 42, and the impurity diffusion layer 43.
  • An electrode 44 made of tungsten silicide, Al, Cu or the like is provided.
  • the electrode 44 serves as the gate of the gate MOS transistor, and can serve as a transfer gate for transferring charges generated in the photodiode 42 to the impurity diffusion layer 43.
  • a wiring layer 45 is formed above the electrode 44. Above the wiring layer 45, a BPSG film 46 and a P-SiN film 48 are provided.
  • the interface between the BPSG film 46 and the P-SiN film 48 is formed so as to be curved downward above the photodiode 42, and serves as an in-layer lens for efficiently guiding incident light to the photodiode 42. Fulfill.
  • a planarizing film layer 49 is formed for the purpose of planarizing the surface of the P-SiN film 48 or uneven portions other than the pixel region.
  • the microlens 15 is a condensing lens arranged with the convex surface facing upward, and is provided above the planarizing film 14 (or a color filter when no planarizing film is provided) and above the light receiving element 42. Each microlens 15 efficiently guides light from the subject to each light receiving element 42.
  • the first colored layer 11 is preferably heated and cured by a heating device such as a hot plate or an oven.
  • the heating temperature is preferably 120 ° C. to 250 ° C., and more preferably 160 ° C. to 230 ° C.
  • the heating time varies depending on the heating means, but is usually about 3 to 30 minutes when heated on a hot plate, and usually about 30 to 90 minutes when heated in an oven.
  • the thickness of the photoresist layer 51 is preferably 0.1 to 3 ⁇ m, preferably 0.2 to 2.5 ⁇ m, and more preferably 0.3 to 2 ⁇ m.
  • the application of the photoresist layer 51 can be suitably performed using the application method for the first colored layer 11 described above.
  • the exposure of the photoresist layer 51 is performed by exposing the positive or negative radiation sensitive composition with g-line, h-line, i-line, etc., preferably i-line, through a predetermined mask pattern. be able to. After the exposure, the photoresist is removed in accordance with a region where a colored pattern is to be formed by developing with a developer.
  • Any developer can be used as long as it dissolves the exposed portion of the positive resist and the uncured portion of the negative resist without affecting the first colored layer containing the colorant.
  • a combination of these organic solvents or an alkaline aqueous solution can be used.
  • an alkaline aqueous solution prepared by dissolving an alkaline compound so as to have a concentration of 0.001 to 10% by mass, preferably 0.01 to 5% by mass is suitable.
  • the etching preferably includes an over-etching process.
  • the overetching process is preferably performed by setting an overetching ratio. Moreover, it is preferable to calculate the overetching ratio from the etching process time to be performed first.
  • the over-etching ratio can be arbitrarily set, but it is preferably 30% or less of the etching processing time in the etching process, and preferably 5 to 25% from the viewpoint of etching resistance of the photoresist and maintaining the rectangularity of the pattern to be etched. Is more preferable, and 10 to 15% is particularly preferable.
  • the resist pattern (that is, etching mask) 52 remaining after the etching is removed.
  • the removal of the resist pattern 52 includes a step of applying a stripping solution or a solvent to the resist pattern 52 so that the resist pattern 52 can be removed, and a step of removing the resist pattern 52 using cleaning water. Is preferred.
  • Examples of the step of removing the resist pattern 52 using cleaning water include a step of removing the resist pattern 52 by spraying cleaning water onto the resist pattern 52 from a spray type or shower type spray nozzle. it can.
  • As the washing water pure water can be preferably used.
  • examples of the injection nozzle include an injection nozzle in which the entire support is included in the injection range, and an injection nozzle that is a movable injection nozzle and in which the movable range includes the entire support. When the spray nozzle is movable, the resist pattern 52 is more effectively moved by spraying the cleaning water by moving from the support center to the support end twice or more during the step of removing the resist pattern 52. Can be removed.
  • the second colored radiation-sensitive composition is embedded in each through-hole in the first through-hole portion group 121 and the second through-hole portion group 122 to obtain a plurality of
  • the second colored radiation-sensitive composition is formed on the first colored layer (that is, the first colored pattern 12 in which the through-hole group 120 is formed in the first colored layer 11) so that the second colored pixel is formed.
  • the second colored radiation-sensitive layer 21 is laminated (step (c)). Thereby, the 2nd coloring pattern 22 which has a some 2nd coloring pixel in the through-hole group 120 of the 1st coloring layer 11 is formed.
  • the second colored pixel is a square pixel.
  • a negative radiation sensitive composition is used for each of the second colored radiation sensitive composition and the third colored radiation sensitive composition.
  • this negative type radiation sensitive composition there is a negative type feeling sensitive to radiation such as ultraviolet rays (g rays, h rays, i rays), deep ultraviolet rays including excimer lasers, electron beams, ion beams and X rays.
  • a radiation composition can be used.
  • g-line, h-line and i-line are preferable, and i-line is particularly preferable.
  • the color filter of the present invention is also suitable as a color filter for a liquid crystal display device.
  • a liquid crystal display device provided with such a color filter can display a high-quality image having a good display image color tone and excellent display characteristics.
  • ⁇ Preparation of pigment dispersion> A mixed solution containing the following compound was mixed for 3 hours with a bead mill (high pressure disperser NANO-3000-10 with a pressure reducing mechanism (manufactured by Nippon BEE Co., Ltd.)) using zirconia beads having a diameter of 0.3 mm. Then, a pigment dispersion was prepared. The types of pigments were as described in Table 1 below, and the amounts of each component were blended so that the composition ratio in the finally obtained colored curable composition would be the ratio described in the following table. ⁇ Pigments (Pigments shown in the table below) Derivative A ⁇ Dispersant A ⁇ Solvent: Propylene glycol monomethyl ether acetate (PGMEA)
  • Halogenated phthalocyanine dye B
  • Halogenated phthalocyanine multimer H (multimer of halogenated phthalocyanine dye E)
  • the halogenated phthalocyanine multimer H is a polymer in which glycidyl methacrylate is added to a polymer composed of a repeating unit derived from the following compound D and a repeating unit derived from methacrylic acid to give a polymerizable double bond group.
  • the synthesis was performed according to the following scheme.
  • compound D (24.2 g), methacrylic acid (1.08 g), dodecyl mercaptan (0.25 g), propylene glycol 1-monomethyl ether 2-acetate (hereinafter also referred to as “PGMEA”) (23. 3 g) was added and heated to 80 ° C. under a nitrogen atmosphere.
  • PGMEA propylene glycol 1-monomethyl ether 2-acetate
  • Non-halogenated phthalocyanine dye A Halogenated phthalocyanine pigment A: (P.G58)
  • Melamine Compound A Nicalak, Sanwa Chemical Co., Ltd.
  • Melamine Compound B 80% solution of a compound containing the structure represented by the following structural formula (Manufactured by Sigma Aldrich)
  • Surfactant A F-781 (Fluorosurfactant manufactured by DIC Corporation)
  • ⁇ Spectroscopic characteristics (film thickness)> The composition obtained above was applied onto a 7.5 cm ⁇ 7.5 cm glass substrate with a spin coater so as to form a coating film having a thickness of 0.6 ⁇ m, and then heated at 100 ° C. using a hot plate. The coating layer was heated and dried for 5 minutes, and further heated at 200 ° C. for 5 minutes to cure the coating film, thereby forming a colored layer.
  • the spectrum of the glass substrate on which the colored layer was formed was measured using MCPD-3000 (manufactured by Otsuka Corporation).
  • ⁇ Chemical resistance> A substrate with a colored layer prepared by the same method as described above from the composition obtained above was immersed in a propylene glycol monomethyl ether acetate solvent for 10 minutes, and then the spectrum of the substrate obtained by rinsing with running water was measured. The absorbance before and after immersion was compared, the color material remaining rate after immersion was calculated from the following formula, and evaluated according to the following categories. In addition, it means that it is excellent in chemical resistance, so that a color material residual rate is high.
  • the patterned glass substrate was attached to an 8-inch silicon wafer, and dry etching was performed according to the following procedure.
  • RF power 800 W
  • antenna bias 400 W
  • wafer bias 200 W
  • chamber internal pressure 4.0 Pa
  • substrate temperature 50 ° C.
  • mixed gas in dry etching apparatus Hitachi High Technologies, U-621
  • the first stage etching process was performed for 80 seconds with the gas type and flow rate being CF 4 : 80 mL / min, O 2 : 40 mL / min, and Ar: 800 mL / min.
  • the above table contains at least a colorant containing a halogenated phthalocyanine dye, a thermosetting compound, and a solvent for dissolving them, and the total content of the colorant is 60 to 90% by mass with respect to the total solid content. It was found that the colored layers (Examples 1 to 19) formed using the colored curable composition were excellent in spectral characteristics, chemical resistance and heat resistance. In particular, it has been found that when an epoxy resin is used as a thermosetting compound and when a methine dye or an azo dye is used as a yellow dye, a remarkable effect is obtained.
  • a colored curable composition with an increased concentration of the colorant can be prepared according to the present invention, and can be expected to be used for preparing a thin film color filter with good color separation.
  • excellent effects can be expected even when the thickness of the colored layer is 0.1 to 1.0 ⁇ m.
  • the combined use of the colored curable composition of the present invention can improve the curability of the pixel and suppress color loss for chemicals (resist stripping solution, alkali developer and general solvent) exposed in various processes. Can be expected to do.
  • it can be expected that thermal diffusion color mixing (heat resistance) to other pixels is suppressed at the time of stacking and a good device sensitivity is achieved.
  • Solid-state image sensor 11 1st colored layer 12 1st colored pattern 13,100 Color filter 14 Flattening film 15 Microlens 20G Green pixel (1st color pixel) 20R red pixel (second color pixel) 20B Blue pixel (third color pixel) 21 2nd coloring radiation sensitive layer 21A The position corresponding to the 1st through-hole part group 121 22 2nd coloring pattern 22R The some 2nd coloring pixel 31 provided in the inside of each through-hole of the 2nd through-hole part group 122 Third colored radiation-sensitive layer 31A Position corresponding to second through-hole portion group 32 Third colored pattern 41 P well 42 Light receiving element (photodiode) 43 Impurity diffusion layer 44 Electrode 45 Wiring layer 46 BPSG film 47 Insulating film 48 P-SiN film 49 Planarizing film layer 51 Photoresist layer 51A Resist through hole 52 Resist pattern (patterned photoresist layer) 120 through-hole group 121 first through-hole part group 122 second through-hole part group

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Abstract

La présente invention concerne une composition colorante durcissable qui contient au moins des agents colorants dont un colorant à l'halogénure de phtalocyanine, un composé thermodurcissable et un solvant qui dissout au moins le colorant à l'halogénure de phtalocyanine et le composé thermodurcissable. La teneur totale en agents colorants est de 60 à 90 % en masse par rapport à la teneur totale en solides.
PCT/JP2013/069346 2012-07-30 2013-07-17 Composition colorante durcissable et filtre couleur utilisant celle-ci WO2014021100A1 (fr)

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