WO2002014912A1 - Composition de filtres colores et filtres colores - Google Patents

Composition de filtres colores et filtres colores Download PDF

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Publication number
WO2002014912A1
WO2002014912A1 PCT/JP2001/006988 JP0106988W WO0214912A1 WO 2002014912 A1 WO2002014912 A1 WO 2002014912A1 JP 0106988 W JP0106988 W JP 0106988W WO 0214912 A1 WO0214912 A1 WO 0214912A1
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Prior art keywords
group
composition
color filter
pigment
phthalocyanine
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PCT/JP2001/006988
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English (en)
Japanese (ja)
Inventor
Takumi Nagao
Michio Morishia
Eisuke Fujiwara
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Mitsubishi Chemical Corporation
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Priority claimed from JP2000267937A external-priority patent/JP4118007B2/ja
Priority claimed from JP2000267938A external-priority patent/JP4301716B2/ja
Priority claimed from JP2000324893A external-priority patent/JP4346230B2/ja
Application filed by Mitsubishi Chemical Corporation filed Critical Mitsubishi Chemical Corporation
Priority to AU2001277782A priority Critical patent/AU2001277782A1/en
Priority to KR10-2003-7002315A priority patent/KR100502529B1/ko
Publication of WO2002014912A1 publication Critical patent/WO2002014912A1/fr

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    • 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
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments

Definitions

  • the present invention relates to a color filter composition used for a liquid crystal display device or a solid-state imaging device and a color filter composition suitable for producing the color filter composition.
  • Color filters used in liquid crystal display devices or solid-state imaging devices are made of fine pixels such as red, green, and blue on a transparent substrate such as glass by dyeing, printing, electrodeposition, or pigment dispersion. Is formed. These conventional methods have the following features and problems.
  • a color filter by the dyeing method is manufactured by forming an image with a photosensitive resin in which dichromate is mixed as a photosensitive agent with gelatin, polyvinyl alcohol, or the like, and then dyeing.
  • the dyeing method is excellent in terms of color reproducibility, an anti-staining step is indispensable for forming multiple colors on the same substrate, and there is a problem that the process becomes complicated.
  • light resistance is poor because a dye is used.
  • the use of dichromate is not desirable from the viewpoint of pollution control.
  • Color fills by printing are manufactured by transferring thermosetting or light-curing ink to a glass substrate by a method such as screen printing or flexographic printing. This method simplifies the process because it does not require image formation and dyeing, but does not provide high-definition images and has problems with ink smoothness.
  • a glass substrate provided with electrodes is immersed in a bath containing a pigment or a dye, and a color filter is formed by electrophoresis.
  • this method is excellent in smoothness, it is difficult to form a complicated pattern because an electrode must be formed on a glass substrate in advance.
  • the production method using pigment-dispersed photosensitive resin pigment dispersion method
  • a composition in which a pigment is dispersed in a photosensitive resin is applied to a transparent substrate such as glass to form a coating film, which is exposed to radiation through a photomask, and exposed to light. Is removed by a development process to form a pattern.
  • a transmissive color liquid crystal display device in which a light source (backlight) is provided on the back of the device and the display is performed by the transmitted light is generally used.
  • An additive color mixing type using three primary colors of green (G) and blue (B) is used.
  • G green
  • B blue
  • the pigment dispersion method In order to increase the green value of the green image of the color filter, the pigment dispersion method has been used to optimize the particle size of the pigment and to improve the yellow pigment to be blended. However, sufficient performance has not yet been obtained.
  • halogenated copper phthalocyanine pigments such as Pigment Green 7, 36 (color index number) are mainly used as green pigments. In these, the transmission spectrum is made longer by introducing a halogen atom into the benzene nucleus of the phthalocyanine skeleton.
  • chlorine atoms or bromine atoms are introduced at almost all of the substitutable positions on the benzene nucleus. It is difficult.
  • an object of the present invention is to provide a composition suitable for producing a high-brightness color filter and a high-brightness color filter obtained using the composition.
  • the present inventors have conducted intensive studies to achieve the above object, and as a result, by using a colorant having a maximum wavelength of the transmission spectrum longer than that of the conventional phthalocyanine pigment, the Y value was increased. Was found to be improved, leading to the present invention.
  • a color material in the first gist of the present invention, a color material, a composition for a color filter containing a binder resin and Z or a monomer, the following general formula (1) or the following general formula: It is characterized by containing at least one phthalocyanine pigment represented by (2).
  • Xi Xw are halogen atoms, and the rest represent any substituents including a hydrogen atom.
  • M represents VO, Al—Z, or In—Z, and Z represents an optional substituent. Represents a group.
  • a color filter containing a phthalocyanine pigment of CI Pigment Green 7 and / or CI Pigment Green 36 as a coloring material, and containing a binder resin and / or a monomer.
  • the composition for use further comprises a fluorinated cyanine pigment having a maximum transmittance wavelength longer than that of CI Pigment Green 7 and CI Pigment Green 36 contained in the composition.
  • a fourth gist of the present invention relates to a color filter formed using the color filter composition. Further, a fifth aspect of the present invention relates to a phthalocyanine-based compound represented by the following general formula (14).
  • X 2 , X 3 , X 6 , X 7 , X 10 are halogen atoms, and Xi, x 4 , x 5 , x 8 , x 9 , x 12 are hydrogen atoms.
  • X 13 , of x 14, x 15, x 16 is any one of the main butoxy group, a sulfonic acid group or a nitro group, the remaining three are hydrogen atoms.
  • M represents a Ga- Z, Z is any Represents a substituent.
  • FIG. 1 is an IR spectrum of a phthalocyanine compound obtained in Production Example 3.
  • Figure 2 shows the MA S S spectrum of the phthalocyanine compound obtained in Production Example 3 [D
  • Figure 3 shows the MASS spectrum of the phthalocyanine-based compound obtained in Production Example 3 [D
  • FIG. 4 is an IR spectrum of the phthalocyanine-based compound obtained in Production Example 4.
  • Figure 5 shows the MASS spectrum of the phthalocyanine compound obtained in Production Example 4 [D
  • Figure 6 shows the MASS spectrum of the phthalocyanine-based compound obtained in Production Example 4 [D
  • FIG. 7 is an IR spectrum of the phthalocyanine-based compound obtained in Production Example 5.
  • FIG. 8 shows the MASS spectrum of the phthalocyanine compound obtained in Production Example 5 [M
  • FIG. 9 is an enlarged view of FIG. BEST MODE FOR CARRYING OUT THE INVENTION>
  • a colorant having a maximum transmission spectrum longer than that of a conventionally used phthalocyanine green pigment is used as a coloring material.
  • a specific phthalocyanine compound include a phthalocyanine compound having Ga—Z, V ⁇ , A1-Z, and In—Z (Z is an arbitrary group) as a central metal.
  • Such phthalocyanine pigments used in the present invention are insoluble in solvents used, such as ether solvents and other organic solvents, in that they are excellent in various properties such as weather resistance. Disperse and exist inside.
  • the phthalocyanine pigment used as a coloring material is represented by the general formula (1).
  • halogen atoms may be any of fluorine, chlorine, bromine and iodine, but fluorine, chlorine and bromine are preferred, and chlorine and bromine are particularly preferred.
  • the number of halogen atoms bonded to the phthalocyanine skeleton needs to be 4 or more, and is preferably 6 or more. For example, those having 6 to 10 halogen atoms are preferably used. Depending on the type of halogen and the substitution position, those having 8 or more halogen atoms may be preferable. Further, plural kinds of halogen atoms may be bonded in one molecule.
  • the bonding position of the halogen atom is not particularly limited, it may be any one of X 2 , X 3 , X 6 , X 7 , X 103 X u , X 14 , and X 15 from the measurement result of the transmission spectrum. I like it.
  • any substituent containing a hydrogen atom refers to a hydrogen atom or Represents any group capable of replacing a hydrogen atom.
  • C is preferably a hydrogen atom, a hydroxyl group, a nitro group, an amino group, an alkylamino group, a cyano group, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, or an aryloxy group.
  • alkylamino group for example, an alkylamino group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, such as a methylamino group, an ethylamino group, a dimethylamino group, and a ethylamino group is used.
  • alkyl group examples include, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, and a sec-butyl group.
  • 1-4 linear or branched alkyl groups are used.
  • a ⁇ -shaped alkyl group having 3 to 10 carbon atoms, preferably 3 to 6 carbon atoms, such as a cyclopropyl group and a cyclobutyl group is also used.
  • alkoxy group examples include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, a tert-butoxy group, a sec-butoxy group, and the like. 1-4 straight-chain or branched alkoxy groups are used. Further, a cyclic alkoxy group having 3 to 10 carbon atoms, preferably 3 to 6 carbon atoms, such as a cyclopropyloxy group and a cyclobutyloxy group is also used.
  • the alkylthio group includes, for example, a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, a tert-butylthio group, a sec-butylthio group, etc. Up to 4 linear or branched alkylthio groups are used. Furthermore, cyclopropylthio group, A cyclic alkylthio group having 3 to 10 carbon atoms, preferably 3 to 6 carbon atoms, such as a butyl thio group, may also be used.
  • aryl group for example, an aryl group having 6 to 10 carbon atoms such as a phenyl group and a naphthyl group is used.
  • aryloxy group for example, an aryloxy group having 6 to 10 carbon atoms such as a phenyloxy group and a naphthyloxy group is used.
  • arylthio group for example, an arylthio group having 6 to 10 carbon atoms such as a phenylthio group or a naphthylthio group is used.
  • aralkyl group for example, an aralkyl group having 7 to 14 carbon atoms such as a phenylmethyl group and a phenylethyl group is used.
  • alkenyl group examples include a linear or branched alkenyl group having 2 to 11 carbon atoms, preferably 2 to 5 carbon atoms, such as a vinyl group, a propenyl group, a butenyl group, and a pentenyl group.
  • cyclic alkenyl groups having 3 to 10 carbon atoms, preferably 3 to 6 carbon atoms, such as cyclopentenyl group and cyclohexenyl are also used.
  • alkenyloxy group for example, a linear or branched alkenyloxy group having 3 to 11 carbon atoms, preferably 2 to 5 carbon atoms, such as a propenyloxy group, a pthenyloxy group, and a pentenyloxy group is used. .
  • alkylcarbonyl group for example, a linear or branched alkylcarbonyl group having 2 to 11 carbon atoms, preferably 2 to 5 carbon atoms, such as an acetyl group, a propionyl group, a butyryl group and an isoptyryl group is used. .
  • alkoxycarbonyl group examples include carbon atoms such as a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an isopropoxycarbonyl group, an n-butoxy force, a carbonyl group, a tert-butoxycarbonyl group, and a sec-butoxycarbonyl group.
  • a linear or branched alkoxycarbonyl group having 2 to 11, preferably 2 to 5 carbon atoms is used.
  • alkylcarbonyl group examples include a methylcarbonyl group, an ethylcarbonyl group, an n-propylcarbonyl group, and an isopropyl group.
  • An oxy group is used.
  • alkylaminocarbonyl group examples include, for example, a methylaminocarbonyl group, an ethylaminocarbonyl group, a dimethylaminocarbonyl group, a acetylaminocarbonyl group, and the like, having 1 to 10 carbon atoms, preferably 1 to 10 carbon atoms.
  • An alkylaminocarbonyl group of 6 is used.
  • alkoxyalkyl group for example, a linear or branched alkoxyalkyl group having 2 to 11 carbon atoms, preferably 2 to 5 carbon atoms, such as a methoxymethyl group, a methoxyxyl group, an ethoxymethyl group, an ethoxyxyl group and the like are used. .
  • fluoroalkyl group examples include a trifluoromethyl group, a penfluorofluoroethyl group, a heptanefluoro-n-propyl group, a heptanefluoroisopropyl group, a perfluoron-butyl group, and a perfluoro-tert-butyl group.
  • a linear or branched fluoroalkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, such as a group or a perfluoro-sec-butyl group is used.
  • fluoroalkoxy group examples include a trifluoromethoxy group, a pentafluoroethoxy group, a heptafluoro-n-propoxy group, a heptafluoroisopropoxy group, a perfluoro-n-butoxy group, a perfluoro-tert-butoxy group, and a A linear or branched fluoroalkoxy group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, such as a fluoro-sec-butoxy group, is used.
  • fluoroalkylthio group examples include a trifluoromethylthio group, a penfluoroethylthio group, a heptanefluoro-n-propylthio group, a heptanefluoroethyl isopropylthio group, a perfluoron-butylthio group, and a perfluoro-ethyl group.
  • a linear or branched fluoroalkylthio group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, such as a tert-butylthio group and a perfluoro-sec-butylthio group is used.
  • alkylsulfonyl group examples include a methylsulfonyl group and an ethylsulfonyl group.
  • alkylaminosulfonyl group examples include alkylaminosulfonyl groups, ethylaminosulfonyl groups, dimethylaminosulfonyl groups, acetylaminosulfonyl groups and the like having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms.
  • a minosulfonyl group is used.
  • alkylaminosulfonic acid salt group examples include, for example, a methylaminosulfonic acid salt group, an ethylaminosulfonic acid salt group, a dimethylaminosulfonic acid salt group, a dimethylaminosulfonic acid salt group and the like having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms.
  • the alkylaminosulfonic acid group of the above is used.
  • aliphatic heterocyclic group for example, an aliphatic heterocyclic group such as a morpholin ring and a piperidine ring is used.
  • aromatic heterocyclic group examples include, for example, pyrrole, furan, thiol, pyridine, oxazolyl, thiazole, imidazolyl, triazolyl, thiadiazolyl, triazine
  • Aromatic heterocyclic groups such as a ring, a benzoxazole ring, a benzothiazole ring, and a benzimidazole ring are used.
  • substituents may further have the above-mentioned substituents.
  • substituents other than a halogen atom are a hydrogen atom, a methoxy group, a sulfonic acid group and a nitro group, and most preferably a hydrogen atom.
  • the number of substituents other than halogen atoms and hydrogen atoms depends on the size of the substituents, but is preferably 8 or less, more preferably 4 or less, in order to maintain the properties as a pigment. Is most preferred.
  • the central part of the phthalocyanine compound in the general formula (1) has a structure of Ga—Z. Coordination of gallium at the center makes the shape of the transmission spectrum sharper than that of other metals, resulting in a pigment with excellent color purity.
  • Moth As Z bonded to the lithium any group can be used, and it is usually any one of a halogen atom, a hydroxyl group, an alkoxy group and an aryloxy group, preferably a halogen atom or a hydroxyl group.
  • the halogen atom may be any of fluorine, chlorine, bromine, iodine and the like, but fluorine, chlorine and bromine are preferred, and chlorine and bromine are particularly preferred.
  • the alkyl group preferably has 8 or less carbon atoms, and particularly preferably 4 or less carbon atoms.
  • the aryl group bonded to oxygen is preferably a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group or the like.
  • the phthalocyanine pigment used as a coloring material in the composition for a color filter according to the first embodiment of the present invention includes two phthalocyanine pigments represented by the general formula (2) via an oxygen atom coordinated to a central metal. May be a dimer to which the phthalocyanine is bonded.
  • the phthalocyanine structural moiety in this dimer is the same as in the general formula (1). That is, at least four of the ⁇ , and at least four of ⁇ 17 ⁇ 32 is it that halogen atoms, also include the same as in the general formula (1) as substituent other than a halogen atom Can be
  • the phthalocyanine moieties constituting the dimer may be the same or different.
  • composition for a color filter according to the first embodiment of the present invention contains at least one of a furocyanine-based pigment represented by the general formula (1) or the general formula (2). That is, the phthalocyanine represented by the general formula (1) or (2) Pigments may be used alone or in combination of two or more.
  • phthalocyanine-based pigments used as coloring materials in the first embodiment of the present invention are exemplified below.
  • the phthalocyanine-based compounds represented by the following general formula (14) can be used as a new pigment for various applications such as Color Fill Yuichi.
  • X 2 , X 3 , X 6 , X 7 , X 10 are halogen atoms, and x, x 4 , x 5 , x 8 , x 9 , x 12 are hydrogen atoms.
  • X 13 , of x 14, x 15, x 16 is any one of the main butoxy group, a sulfonic acid group or a nitro group, the remaining three are hydrogen atoms.
  • M represents a G a- Z
  • Z is a halogen Represents an arbitrary substituent such as an atom, a hydroxyl group, an alkoxy group or an aryloxy group.
  • phthalocyanine pigments include, for example, phthalonitrile, phthalic acid, phthalic anhydride, phthalimid, diiminoisoindoline Heating a mixture of a halide such as gallium and, if necessary, a gallium compound such as gallium chloride or gallium bromide as a starting material with a mixture of the unsubstituted compound, which is substituted with a compound other than a halogene, as necessary.
  • a halogen represents an arbitrary substituent such as an atom, a hydroxyl group, an alkoxy group or an aryloxy group.
  • a phthalocyanine in which a different substituent is bonded to any benzene nucleus can be synthesized.
  • a substituted or unsubstituted compound other than halogen such as drin as a starting material
  • a substituted or unsubstituted fluorinated cyanine other than halogen may be synthesized, and then halogenated by a known method.
  • gallium phthalocyanine cloguchi may be hydrolyzed by a known method.
  • a method of heat-treating gallium phthalocyanine or hydroxygaridine phthalocyanine in an alcohol solvent such as methanol or ethanol is used.
  • a base such as sodium alkoxide and sodium hydride may coexist in the alcohol solvent.
  • a method of heat-treating gallium phthalocyanine or hydroxygallium phthalocyanine in a solvent containing a hydroxy derivative of an aromatic compound or the like is used.
  • a base such as sodium alkoxide or sodium hydride may coexist in a solvent containing a hydroxy derivative of an aromatic compound.
  • the dimer can be obtained, for example, by synthesizing gallium phthalocyanine cloguchi, hydrolyzing it by a known method to give hydroxygallium phthalocyanine, and then dehydrating by heating in an organic solvent.
  • the phthalocyanine-based pigment obtained by synthesis has a non-uniform particle size, and is often unsuitable for use as a composition for a color filter. Also, some crystal types may be mixed. Therefore, usually, a so-called pigmentation is performed on the phthalocyanine or the dimer obtained by the synthesis to adjust the particle size to the crystal form to a desired value. Pigmentation is performed by dissolving a pigment in a strong acid such as concentrated sulfuric acid, fuming sulfuric acid, chlorosulfonic acid, or polyphosphoric acid, or a mixture thereof, and pouring the pigment into a large amount of water to form an acid paste that forms a fine pigment.
  • a strong acid such as concentrated sulfuric acid, fuming sulfuric acid, chlorosulfonic acid, or polyphosphoric acid, or a mixture thereof
  • pigments formed by any of the above methods can be used, but it is preferable to use an acid paste method, an acid slurry method, or a solvent treatment.
  • a pigment is formed by an acid paste method or an acid slurry method, it is preferable to neutralize with an alkali or the like after treatment with a strong acid, but at this time, the alkalinity may change the permeation spectrum. So be careful. It is preferable to use concentrated sulfuric acid as the strong acid.
  • a sulfone group or the like may be introduced into the phthalocyanine skeleton.
  • the central metal is Ga, Al, In, or the like, the halogen in Z may be substituted with hydroxy or may form a dimer, which may be a mixture of a plurality of compounds. .
  • the phthalocyanine pigment used as a coloring material is represented by the general formula (7).
  • the halogen atom may be any of fluorine, chlorine, bromine and iodine, but fluorine, chlorine and bromine are preferred, and chlorine and bromine are particularly preferred.
  • the number of halogen atoms bonded to the phthalocyanine skeleton needs to be 4 or more, preferably 6 or more, and more preferably 8 or more. For example, those having 6 to 10 halogen atoms are used. However, the number of halogen atoms bonded to the phthalocyanine skeleton is usually 16 or less. Further, plural kinds of halogen atoms may be bonded in one molecule.
  • the substituent bonded to the remaining positions is any substituent containing a hydrogen atom, but is soluble in a solvent such as a phenoxy group having a substituent at the ortho position in the sense of securing low solubility as a pigment.
  • a solvent such as a phenoxy group having a substituent at the ortho position in the sense of securing low solubility as a pigment.
  • Substituents tend to be less preferred, such as a hydrogen atom, a hydroxyl group, a nitro group, an amino group, a cyano group, an alkyl group having 1 to 4 carbon atoms, a cyclic alkyl group having 3 to 6 carbon atoms, and a carbon atom.
  • alkyl group having 1 to 4 carbon atoms examples include linear or branched alkyl groups such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, tert-butyl group and sec-butyl group. Is used.
  • Examples of the cyclic alkyl group having 3 to 6 carbon atoms include a cyclopropyl group and a cyclobutyl group.
  • alkoxy group having 1 to 4 carbon atoms examples include linear or branched linear groups such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy and sec-butoxy. Things are used.
  • Examples of the cyclic alkoxy group having 3 to 6 carbon atoms include a cyclopropyloxy group and a cyclobutyloxy group.
  • alkylthio group having 1 to 4 carbon atoms examples include straight-chain or branched alkylthio groups such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, tert-butylthio, and sec-butylthio. Is used.
  • Examples of the cyclic alkylthio group having 3 to 6 carbon atoms include a cyclopropylthio group and a cyclobutylthio group.
  • alkenyl group having 2 to 5 carbon atoms for example, a linear or branched one such as a vinyl group, a propenyl group, a butenyl group, and a pentenyl group is used.
  • Examples of the cyclic alkenyl group having 3 to 6 carbon atoms include a cyclopentenyl group and a cyclohexenyl group.
  • alkenyloxy group having 2 to 5 carbon atoms examples include a propenyloxy group, Linear or branched ones such as a butenyloxy group and a pentenyloxy group are used.
  • alkylcarbonyl group having 2 to 5 carbon atoms for example, a linear or branched one such as an acetyl group, a propionyl group, a butyryl group and an isoptyryl group is used.
  • alkoxycarbonyl group having 2 to 5 carbon atoms examples include methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, tert-butoxycarbonyl group, sec— A straight or branched one such as a butoxycarbonyl group is used.
  • alkylcarbonyloxy group having 2 to 5 carbon atoms examples include a methylcarbonyloxy group, an ethylcarbonyloxy group, an n-propylcarbonyloxy group, an isopropylcarbonyloxy group, an n-butylcarbonyloxy group, and tert. — Linear or branched ones such as —butylcarbonyloxy group and sec—butylbutyloxy group;
  • alkylaminocarbonyl group having 1 to 6 carbon atoms for example, a methylaminocarbonyl group, an ethylaminocarbonyl group, a dimethylaminocarbonyl group, a acetylaminocarbonyl group and the like are used.
  • fluoroalkyl group having 1 to 4 carbon atoms examples include, for example, trifluoromethyl group, pentafluoroethyl group, heptafluoro-n-propyl group, heptafluorofluoropropyl group, perfluoro-n-butyl group, and perfluoro-tert-butyl.
  • a linear or branched one such as a group or a perfluoro-sec-butyl group is used.
  • Examples of the fluoroalkoxy group having 1 to 4 carbon atoms include a trifluoromethoxy group, a penfluorofluoroethoxy group, a heptanefluoro-n-propoxy group, a heptanefluorisopropoxy group, and a perfluoro-n-butoxy group.
  • a linear or branched one such as a perfluoro-tert-butoxy group, a perfluoro-sec-butoxy group and the like is used.
  • fluoroalkylthio group having 1 to 4 carbon atoms examples include a trifluoromethylthio group, a penfluorofluorothiol group, a heptanefluoro-n-propylthio group, a heptanefluoroisopropylthio group, and a perfluorofluoron group —Butylthio group, perf A straight-chain or branched one such as a ro-tert-butylthio group or a perfluoro-sec-butylthio group is used.
  • alkylsulfonyl group having 1 to 4 carbon atoms examples include methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, tert-butylsulfonyl, sec-butylsulfonyl A straight or branched group such as a group is used.
  • alkylaminosulfonyl group having 1 to 6 carbon atoms examples include a methylaminosulfonyl group, an ethylaminosulfonyl group, a dimethylaminosulfonyl group, and a acetylaminosulfonyl group.
  • alkylaminosulfonic acid group having 1 to 6 carbon atoms examples include a methylaminosulfonic acid group, an ethylaminosulfonic acid group, a dimethylaminosulfonic acid salt group, and a ethylaminosulfonic acid group.
  • aliphatic heterocyclic group for example, a morpholin ring, a piperidine ring and the like are used.
  • aromatic heterocyclic group examples include a pyrrole ring, a furan ring, a thiol ring, a pyridine ring, an oxazolyl ring, a thiazolyl ring, an imidazole ring, a triazolyl ring, a thiadiazole ring, a triazine ring, and a benzoyl group.
  • Oxazole ⁇ , benzothiazole ⁇ , benzoimidazole ring and the like are used.
  • substituents may further have the above-mentioned substituents.
  • a particularly preferable substituent other than a halogen atom is a hydrogen atom.
  • the number of substituents other than a halogen atom and a hydrogen atom depends on the size of the substituent and the like, but is preferably 2 or less in order to maintain properties as a pigment.
  • the central part of the phthalocyanine compound in the general formula (7) usually has a structure of VO, A 1 -Z, and In-Z.
  • Z bonded to aluminum or indium is an arbitrary substituent, but is usually any one of a halogen atom, a hydroxyl group, an alkoxy group and an aryloxy group, preferably a halogen atom or a hydroxyl group.
  • the halogen atom may be any of fluorine, chlorine, bromine, iodine, etc., but fluorine, chlorine, Bromine is preferred, and chlorine and bromine are particularly preferred.
  • the alkoxy group the alkyl group preferably has 8 or less carbon atoms, particularly preferably 4 or less.
  • the aryl group bonded to oxygen is preferably a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group or the like.
  • the phthalocyanine-based pigment used as a coloring material in the color filter composition according to the second embodiment of the present invention is represented by the following general formula (8): It may be a dimer in which two phthalocyanines are bonded via an oxygen atom coordinated to a central metal.
  • the phthalocyanine structural moiety in this dimer is the same as in the general formula (7). That is, And at least four of X 17 to X 32 must each be a halogen atom, and the substituents other than the halogen atom are the same as those in the general formula (7). Things are used.
  • a substituent other than a halogen atom and a hydrogen atom is preferably at which it 2 or less.
  • each phthalocyanine moiety constituting the dimer may be the same or different.
  • the color filter composition according to the second embodiment of the present invention contains at least one of the phthalocyanine pigments represented by the general formula (7) or (8). That is, the phthalocyanine pigment represented by the general formula (7) or (8) may be used alone or in combination of two or more. Some examples of the phthalocyanine pigment used as a coloring material in the second embodiment of the present invention are described below.
  • phthalocyanine pigments include, for example, halides such as phthalonitrile, phthalic acid, phthalic anhydride, phthalimid, diiminoisoindoline, and, if necessary, unsubstituted derivatives thereof. It can be synthesized by a known method of heating a mixture with a compound substituted with a metal compound such as vanadium chloride, aluminum chloride, or indium chloride as a starting material.
  • a phthalocyanine in which a different substituent is bonded to any benzene nucleus can be synthesized.
  • a substituted or unsubstituted compound other than halogen such as phthalonitrile, phthalic anhydride, phthalimid, diiminoisoindrin, etc.
  • a substituted or unsubstituted phthalocyanine other than halogen is synthesized and then synthesized. Halogenation may be performed by the method described above.
  • chloroaluminum phthalocyanine or chloroindium phthalocyanine may be hydrolyzed by a known method.
  • a base such as sodium alkoxide and sodium hydride may coexist in a solvent containing a hydroxy derivative of an aromatic compound or the like.
  • the dimer is obtained by, for example, synthesizing aluminum phthalocyanine and aluminum indium phthalocyanine, hydrolyzing them by a known method to obtain hydroxyaluminum phthalocyanine and hydroxyindium phthalocyanine, and further heating and dehydrating in an organic solvent. Can be obtained.
  • the phthalocyanine-based pigment obtained by synthesis has a non-uniform particle size, and is often not suitable for use as a color filter composition until it is obtained. Also, some crystal types may be mixed. Therefore, usually, a so-called pigmentation is performed on the phthalocyanine or the dimer obtained by the synthesis to adjust the particle size to the crystal form to a desired value. Pigmentation is carried out by dissolving a pigment in a strong acid such as concentrated sulfuric acid, fuming sulfuric acid, chlorosulfonic acid, or polyphosphoric acid, or a mixture thereof, and pouring it into a large amount of water to produce a fine paste.
  • a strong acid such as concentrated sulfuric acid, fuming sulfuric acid, chlorosulfonic acid, or polyphosphoric acid, or a mixture thereof
  • a pigment is dispersed in a strong acid and poured into a large amount of water to produce a fine pigment.
  • a fine pigment is obtained by adding a mineral salt such as sodium chloride and a solvent to phthalocyanine or a dimer thereof using a ball mill or a dimer, and then grinding the mixture to remove the inorganic salt and the solvent.
  • a salt milling method is to obtain. If the particle size is too small, there is a method in which a crystal is grown by heat treatment in an organic solvent.
  • pigments formed by any of the above methods can be used, but it is preferable to use an acid paste method, an acid slurry method or a solvent treatment.
  • an acid paste method an acid slurry method or a solvent treatment.
  • a pigment is formed by the acid paste method or the acid slurry method, it is preferable to neutralize with a strong acid or the like after the treatment with a strong acid. Attention is necessary because there are cases. It is preferable to use concentrated sulfuric acid as the strong acid.
  • a pigment is formed by an acid paste method or an acid slurry method, a sulfone group or the like may be introduced into the phthalocyanine skeleton.
  • the halogen in Z may be substituted with hydroxy or may form a dimer, which may be a mixture of a plurality of compounds.
  • the solvent used for the solvent treatment include the same solvents as those used for the color fill composition described below, and it is preferable to perform the heat treatment with the same solvent.
  • Pigment Green 7 (hereinafter, sometimes referred to as PG7) and No or Pigment Green 36 (hereinafter, sometimes referred to as PG36) as coloring materials.
  • PG7 Pigment Green 7
  • PG36 No or Pigment Green 36
  • a phthalocyanine pigment having a maximum transmittance wavelength longer than those of the pigments used is used.
  • the central metals of such phthalocyanine pigments include Cu, Ni, Co, Fe, Zn, Pd, Mg, Ru, Rh.Pt, Mn, Ti, Be, Ca, Ba, Cd, H Pb , Sn, Ag, 2-valent metal such as An; a 1- Z, In- Z , Ga- Z, Tl- Z, Mn- Z, F e - Z Ru- Z , etc.
  • a dimer having the above L 1 or L 2 —Z as a central metal, and the L 1 or L 2 being bonded to the central metal of another fluorinated cyanine compound via an oxygen atom is also included. It is preferably used.
  • Z is an arbitrary substituent, and among them, a halogen atom, a hydroxyl group, an alkoxy group or an aryloxy group is preferable.
  • a halogen atom such as a fluorine atom, a chlorine atom, and a bromine atom
  • a carbon atom whose alkyl chain portion such as a methoxy group, an ethoxy group, a butoxy group, and a hexyloxy group has a straight, branched, or cyclic carbon atom
  • an aryl group such as a phenoxy group, a naphthyloxy group, a pyridyloxy group or a quinolyloxy group, having a 5-membered, 6-membered, 5-membered and Z- or 6-membered ring; Or one of three fused rings —Ruoxy group and the like.
  • a compound represented by (13), which is a dimer of the following general formula (12) or (12), is particularly preferable.
  • M is a divalent metal
  • ⁇ ⁇ _ ⁇ (where L 1 is trivalent
  • the ⁇ in the above may be the same or different.)
  • Represents a tetravalent substituted metal represented by, an oxymetal represented by L 3 0, or a lanthanide.
  • M is L 1 or L 2 — represents Z (however, L, L 2 and Z have the same meanings as in general formula (1 2))
  • halogen atoms may be any of a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, but is preferably a fluorine atom, a chlorine atom and a bromine atom, particularly preferably a chlorine atom or a bromine atom.
  • the number of halogen atoms bonded to the phthalocyanine skeleton needs to be 4 or more, and is preferably 6 or more. For example, those having 6 to 10 halogen atoms are used. Depending on the type of halogen and the substitution position, those having 8 or more halogen atoms may be preferable. Further, plural kinds of halogen atoms may be bonded in one molecule.
  • the bonding position of the halogen atom is not particularly limited, but is preferably any of X 2 , X 3 , X 65 X 7 , X 105 X 115 X 14 , and X 15 from the result of transmission spectrum measurement. .
  • the substituents bonded to the remaining positions are not particularly limited.
  • Preferred are a hydrogen atom, a hydroxyl group, a nitro group, an amino group, an alkylamino group, a cyano group, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, Aralkyl, alkenyl, alkenyloxy, alkylcarbonyl, alkoxycarbonyl, alkylcarbonyloxy, alkylaminocarboxy, alkoxyalkyl, fluoroalkyl, fluoroalkoxy, fluoro Alkylthio, carboxyl, formyl, sulfonic, alkylsulfonyl, alkylaminosulfonyl, alkylaminosulfonate, chlorosulfone, carbamide, sulfonamide, aliphatic heterocyclic, and aromatic And a heterocyclic
  • alkylamino group for example, an alkylamino group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, such as a methylamino group, an ethylamino group, a dimethylamino group, and a ethylamino group is used.
  • alkyl group examples include, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, a sec-butyl group, and the like. 1-4 straight-chain or branched alkyl groups are used. Further, a cyclic alkyl group having 3 to 10 carbon atoms, preferably 3 to 6 carbon atoms, such as a cyclopropyl group and a cyclobutyl group, is also used.
  • alkoxy group examples include a methoxy group, an ethoxy group, an ⁇ -propoxy group, an isopropoxy group, an n-butoxy group, a tert-butoxy group, a sec-butoxy group, and the like. 1-4 straight-chain or branched alkoxy groups are used. Further, a cyclic alkoxy group having 3 to 10 carbon atoms, preferably 3 to 6 carbon atoms, such as a cyclopropyloxy group and a cyclobutyloxy group is also used.
  • alkylthio group examples include, for example, a methylthio group, an ethylthio group, an n-propylthio group, an isopropylthio group, an n-butylthio group, a tert-butylthio group, a sec-butylthio group, and the like. Up to 4 linear or branched alkylthio groups are used. Further, a cyclic alkylthio group having 3 to 10 carbon atoms, preferably 3 to 6 carbon atoms, such as a cyclopropylthio group and a cyclobutylthio group, is also used.
  • aryl group examples include phenyl, naphthyl and the like having 6 to 10 carbon atoms.
  • Aryl groups are used.
  • aryloxy group for example, an aryloxy group having 6 to 10 carbon atoms such as a phenyloxy group and a naphthyloxy group is used.
  • arylthio group for example, an arylthio group having 6 to 10 carbon atoms such as a phenylthio group and a naphthylthio group is used.
  • aralkyl group for example, an aralkyl group having 7 to 14 carbon atoms such as a phenylmethyl group and a phenylethyl group is used.
  • alkenyl group for example, a linear or branched alkenyl group having 2 to 11 carbon atoms, preferably 2 to 5 carbon atoms, such as a vinyl group, a propenyl group, a butenyl group, and a pentenyl group is used. Furthermore, cyclic alkenyl groups having 3 to 10 carbon atoms, preferably 3 to 6 carbon atoms, such as cyclopentenyl group and cyclohexenyl are also used.
  • alkenyloxy group for example, a linear or branched alkenyloxy group having 3 to 11 carbon atoms, preferably 2 to 5 carbon atoms, such as a propenyloxy group, a pthenyloxy group, and a pentenyloxy group is used. .
  • alkylcarbonyl group for example, a linear or branched alkylcarbonyl group having 2 to 11 carbon atoms, preferably 2 to 5 carbon atoms, such as an acetyl group, a propionyl group, a butyryl group, and an isoptyryl group is used. .
  • alkoxycarbonyl group examples include those having 2 to 2 carbon atoms such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, tert-butoxycarbonyl, sec-butoxycarbonyl and the like.
  • a straight-chain or branched alkoxycarbonyl group having 1 to 1, preferably 2 to 5 carbon atoms is used.
  • alkylcarbonyloxy group examples include a methylcarbonyloxy group, an ethylcarbonylcarbonyl group, an n-propylcarbonyloxy group, an isopropyl group, a carbonyloxy group, an n-butylcarbonyloxy group, and a tert-butylcarbonyloxy group.
  • a linear or branched alkylcarbonyloxy group having 2 to 11 carbon atoms, preferably 2 to 5 carbon atoms, such as a group or sec-butylcarbonyloxy group is used.
  • alkylaminocarbonyl group examples include, for example, a methylaminocarbonyl group, an ethylaminocarbonyl group, a dimethylaminocarbonyl group, a acetylaminocarbonyl group, and the like, having 1 to 10 carbon atoms, preferably 1 to 10 carbon atoms.
  • An alkylaminocarbonyl group of 6 is used.
  • alkoxyalkyl group for example, a linear or branched alkoxyalkyl group having 2 to 11 carbon atoms, preferably 2 to 5 carbon atoms, such as a methoxymethyl group, a methoxyxyl group, an ethoxymethyl group, and an ethoxyxyl group is used. .
  • fluoroalkyl group examples include a trifluoromethyl group, a pentafluoroethyl group, a heptafluoro-n-propyl group, a heptafluoroisopropyl group, a perfluoro-n-butyl group, a perfluoro-tert-butyl group, A linear or branched fluoroalkyl group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, such as one fluoro sec-butyl group is used.
  • fluoroalkoxy group examples include a trifluoromethoxy group, a pentaphenylenoethoxy group, a heptafluoro-n-propoxy group, a heptafluoroisopropoxy group, a perfluoro-n-butoxy group, a perfluoro-tert-butoxy group, A linear or branched fluoroalkoxy group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, such as a perfluoro-sec-butoxy group is used.
  • fluoroalkylthio group examples include a trifluoromethylthio group, a penfluorofluorothio group, a heptanefluoro-n-propylthio group, a heptanefluoroisopropylthio group, a perfluoron-butylthio group, A linear or branched fluoroalkylthio group having 1 to 10 carbon atoms, preferably 1 to 4 carbon atoms, such as a perfluoro-tert-butylthio group-fluoro-sec-butylthio group, is used.
  • alkylsulfonyl group examples include, for example, methyl sulfonyl group, ethylsulfonyl group, II-propylsulfonyl group, isopropylsulfonyl group, n-butylsulfonyl group, tert-butylsulfonyl group, sec-butylsulfonyl group, etc.
  • alkylaminosulfonyl group examples include alkylaminosulfonyl groups, ethylaminosulfonyl groups, dimethylaminosulfonyl groups, acetylaminosulfonyl groups and the like having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms.
  • a minosulfonyl group is used.
  • alkylaminosulfonic acid salt group examples include, for example, a methylaminosulfonic acid salt group, an ethylaminosulfonic acid salt group, a dimethylaminosulfonic acid salt group, a dimethylaminosulfonic acid salt group and the like having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms.
  • the alkylaminosulfonic acid group of the above is used.
  • aliphatic heterocyclic group for example, an aliphatic heterocyclic group such as a morpholin ring and a bipyridine ring is used.
  • aromatic heterocyclic group examples include, for example, pyrrole, furan, thiol, pyridine, oxazole, thiazolyl, imidazolyl, triazole, thiadiazolyl, triazine, An aromatic heterocyclic group such as a benzoxazole ring, a benzothiazole ring, or a benzoimidazole ring is used.
  • substituents may further have the above-mentioned substituents.
  • a sulfone group, a carbamide group, a sulfoneamide group, an aliphatic heterocyclic group, and an aromatic heterocyclic group are more preferred, and a hydrogen atom, an alkoxy group, a sulfonic acid group, and a nitro group are particularly preferred.
  • the number of substituents other than a halogen atom and a hydrogen atom depends on the size of the substituents and the like, but is preferably 8 or less, more preferably 4 or less, in order to maintain properties as a pigment. Most preferably, two or less.
  • Z is an optional substituent, but is preferably a halogen atom, a hydroxyl group, an alkoxy group or an aryloxy group.
  • the hydrogen atom and the halogen atom may be any of a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, but are preferably a fluorine atom, a chlorine atom and a bromine atom, particularly preferably a chlorine atom or a bromine atom.
  • the alkoxy group the alkyl group preferably has 8 or less carbon atoms, and particularly preferably 4 or less.
  • the aryl group bonded to oxygen is preferably a phenyl group, a naphthyl group, a pyridyl group, a quinolyl group or the like.
  • the phthalocyanine structure in the dimer represented by the general formula (13) is the same as that of the general formula (12). That is, at least four of Xi X, and at least four of X 17 to X 32 are each a halogen atom, and the substituents other than the halogen atom are the same as those in the general formula (12). No. Each phthalocyanine moiety constituting the dimer may be the same or different.
  • M is represented by L 1 or L 2 —Z (provided that ⁇ L 2 and Z are the same as those in the general formula (12)). , Ga, Fe, Si-Z, Sn-Z, and Ti-Z, more preferably Ga, Al, In, and particularly preferably Ga.
  • the pigment having the maximum transmittance wavelength on the longer wavelength side than Pigment Green 7 or Pigment Green 36 to be used is described in the description of the first and second embodiments.
  • the phthalocyanine pigment represented by the above-mentioned general formula (1), (2), (7) or (8) is used.
  • a coloring material having a maximum transmittance wavelength on a longer wavelength side represented by a phthalocyanine pigment represented by the general formula (12) or (13), is used alone. Or two or more of them may be used in combination, and the mixing amount of the coloring material is 100 with respect to the total weight ratio of Pigment Green 7 and / or Pigment Green 36.
  • the color material is usually 100 or less, preferably 70 or less, more preferably 50 or less, and the lower limit is usually 1 or more, preferably 3 or more, more preferably 5 or more in weight ratio.
  • phthalocyanine pigments represented by the general formula (12) or (13) used as a coloring material in the present invention are exemplified below.
  • phthalocyanine-based pigments include, for example, substituted or unsubstituted phthalonitrile, phthalic acid, phthalic anhydride, phthalimid, diiminoisoindoline, etc.
  • the mixture can be synthesized by a known method in which a mixture is used as a starting material and heated with a corresponding metal halide such as a metal chloride or metal bromide.
  • a phthalocyanine in which different substituents are bonded to any benzene nucleus can be synthesized.
  • a substituted or unsubstituted phthalocyanine such as phthalonitrile, phthalic anhydride, phthalimid, diiminoisoindrin or the like is used as a starting material to synthesize a substituted or unsubstituted phthalocyanine.
  • Reaction such as chlorination, chlorosulfonation, or nitration may be performed.
  • a hydroxyl group can be coordinated to the central metal by, for example, hydrolyzing chromium gallium phthalocyanine, chromium aluminum phthalocyanine, chloroindimifu cyanine, or the like by a known method. Good.
  • a method of heating gallium phthalocyanine or hydroxygallium phthalocyanine in an alcohol solvent such as methanol or ethanol is used. .
  • a base such as sodium alkoxide or sodium hydride may coexist in the alcohol solvent.
  • a chromium-containing gallium phthalocyanine, a hydroxygallium phthalocyanine, or a hydroxy derivative of an aromatic compound may be used.
  • a method of performing heat treatment in a solvent containing is used.
  • a base such as sodium alkoxide or sodium hydride may coexist in a solvent containing a hydroxy derivative of an aromatic compound.
  • the dimer can be obtained, for example, by synthesizing gallium phthalocyanine or the like, hydrolyzing it by a known method to obtain hydroxygallium phthalocyanine, and then dehydrating by heating in an organic solvent.
  • the phthalocyanine-based pigment obtained by synthesis has a non-uniform particle size, and until that time, it is often unsuitable for use as a color-fill composition. Also, some crystal types may be mixed. Therefore, usually, a so-called pigmentation is performed on the phthalocyanine or the dimer obtained by the synthesis to adjust the particle size to the crystal form to a desired value.
  • Pigmentation is carried out by dissolving a pigment in a strong acid such as concentrated sulfuric acid, fuming sulfuric acid, chlorosulfonic acid, or polyphosphoric acid, or a mixture thereof, and pouring it into a large amount of water to produce a fine paste.
  • a strong acid such as concentrated sulfuric acid, fuming sulfuric acid, chlorosulfonic acid, or polyphosphoric acid, or a mixture thereof
  • an acid slurry method in which a pigment is dispersed in a strong acid and poured into a large amount of water to produce a fine pigment.
  • a ball mill or a kneader is used, and an inorganic salt such as sodium chloride and a solvent are added to phthalocyanine or a dimer thereof, and a solvent is obtained by grinding and then removing the inorganic salt and the solvent to obtain a fine pigment.
  • a tomilling method and the like If the particle size is too small, there is a method in which a crystal is grown by heat
  • pigments formed by any of the above methods can be used, but it is preferable to use an acid paste method, an acid slurry method, or a solvent treatment.
  • a pigment is formed by the acid paste method or the acid slurry method, it is preferable to neutralize with alkali or the like after the treatment with a strong acid. It is necessary to be careful because there is. It is preferable to use concentrated sulfuric acid as the strong acid.
  • a pigment is formed by an acid paste method or an acid slurry method, a sulfone group or the like may be introduced into the phthalocyanine skeleton.
  • the central metal is Ga, Al, In, or the like, the halogen in Z may be substituted with hydroxy or may form a dimer, which may be a mixture of a plurality of compounds. .
  • a pigment by a combination of a solvent treatment after the treatment with the acid paste method or the acid slurry method, since the transmittance can be improved.
  • the solvent used for the solvent treatment include the same solvents as those used for the color fill composition described below, and it is preferable to perform the heat treatment with the same solvent. Note that an embodiment including a plurality of the first to third embodiments is also an embodiment of the present invention. Hereinafter, portions common to the first to third aspects will be described.
  • the specific phthalocyanine pigment used in the first to third embodiments usually has a maximum transmittance wavelength at a wavelength of 5 17 nm or more. As a result, a better Y value can be obtained. In addition, it is not realistic to have the maximum transmittance on the long wavelength side too much, and on the contrary, the characteristics may be deteriorated. Therefore, the maximum transmittance wavelength is usually 58 O nm or less, preferably 56 O nm. Hereinafter, it is more preferably 55 O nm or less.
  • the composition for color fill evening according to the present invention contains a binder resin and / or a monomer.
  • the binder resin and the monomer may be appropriately selected in consideration of the production process of the color filter.
  • the binder resin When the binder resin is used alone, an appropriate one is selected in consideration of the desired image formability and performance, the production method to be adopted, and the like.
  • the binder resin When a binder resin is used in combination with a monomer described below, the binder resin is added to modify the composition for color filling and improve the physical properties after photocuring. Therefore, in this case, the binder resin is appropriately selected according to the purpose of improving the compatibility, the film forming property, the developing property, the adhesive property, and the like.
  • binder resins examples include (meth) acrylic acid, (meth) acrylate, (meth) acrylamide, maleic acid, (meth) acrylonitrile, styrene, vinyl acetate, vinylidene chloride, and maleimide.
  • Homo- or copolymers such as polyethylene oxide, polyvinylpyrrolidone, polyamide, polyurethane, polyester, polyether, polyethylene terephthalate, acetylcellulose, novolak resin, resin resin, polyvinylphenol or Po And vinyl vinyl butyral.
  • binder resins preferred are those containing a carboxyl group or a phenolic hydroxyl group in the side chain or main chain. If a resin having these functional groups is used, development with an alkaline solution becomes possible.
  • a resin having a high alkali developability and having a carboxyl group such as an acrylic acid (co) polymer, a styrene z maleic anhydride resin, or a resin modified with an acid anhydride of novolac epoxy acrylate is preferred. is there.
  • an acrylic resin is particularly preferred.
  • This resin is excellent in developability and transparency, and can obtain various copolymers by selecting various monomers, so that the performance and the production method can be easily controlled.
  • acryl-based resin examples include (meth) acrylic acid and / or succinic acid (2- (meth) acryloyl mouth xicetyl) ester, adipic acid (2-acrylic mouth xicetyl) ester, and fluoric acid (2- (meta) ) Acryloyl mouth kissil) Ester, Hexahydrofuric acid (2- (meth) acryloyl mouth kissille) ester, maleic acid (2- (meth) acryloy mouth kissille) ester, succinic acid (2-
  • (Anhydrous) Compounds to which acids (anhydrides) such as fluoric acid and (anhydrous) maleic acid have been added As an essential component, if necessary, styrene-based monomers such as styrene, monomethyl-styrene, and vinyl toluene; unsaturated group-containing carboxylic acids such as cinnamic acid, maleic acid, fumaric acid, maleic anhydride, and itaconic acid; methyl (Meth) acrylate, ethyl (methyl) acrylate, propyl (meth) acrylate, aryl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, hydroxyethyl (meth) acrylate Esters of (meth) acrylic acid such as, hydroxypropyl (meth) acrylate, pendyl (meth) acrylate, hydroxyphenyl (meth)
  • lactones such as (meth) acrylic acid to £ -force prolactone, ⁇ -propiolactone, a-lactide lactone, 5-valerolactone; acrylonitrile; (meth) acrylylamide; N Acrylamides such as methylol acrylamide, N, N-dimethylacrylamide, N-methylacryloylmorpholine, N, N-dimethylaminoethyl (meth) acrylate, N, N-dimethylaminoethylacrylamide Resins obtained by copolymerizing various monomers such as vinyl acetate, vinyl versatate, vinyl propionate, vinyl cinnamate, and vinyl acid bielate.
  • styrene In order to increase the strength of the coating film, styrene, methyl styrene, benzyl (meth) acrylate, hydroxyphenyl (meth) acrylate, methoxyphenyl (meth) acrylate, hydroxyphenyl (meth) acrylamide And a monomer having a phenyl group such as hydroxyphenyl (meth) acrylsulfonamide, in an amount of from 10 to 98 mol%, preferably from 20 to 80 mol%, more preferably from 30 to 70 mol%.
  • (meth) acrylic acid means “acrylic acid or methacrylic acid”
  • (meth) acrylate, (meth) acryloyl group and the like have the same meaning.
  • these resins preferably have an ethylenic double bond in a side chain.
  • a binder resin having a double bond in a side chain the photocurability of the composition for a color filter according to the present invention is increased, so that the resolution and adhesion can be further improved.
  • Means for introducing an ethylenic double bond into the binder resin include, for example, the methods described in Japanese Patent Publication No. 50-344443, Japanese Patent Publication No. Examples of the method include a method of reacting a compound having a glycidyl group or an epoxycyclohexyl group with a (meth) acryloyl group, and a method of reacting acrylic acid chloride with a hydroxyl group of a resin.
  • glycidyl (meth) acrylate aryl glycidyl ether, glycidyl monoethyl acrylate, crotonyl glycidyl ether, glycidyl ether (iso) crotonate, (3,4-epoxycyclohexyl) methyl
  • a binder resin having an ethylenic double bond group in the side chain can be obtained.
  • a resin obtained by reacting an alicyclic epoxy compound such as (3,4-epoxycyclohexyl) methyl (meth) acrylate is preferable as the binder resin.
  • an ethylenic double bond is introduced into a resin having a carboxylic acid group or a hydroxyl group in advance, 2 to 50% by mole, preferably 5 to 40% by mole of the carboxyl group or the hydroxyl group of the resin. It is preferable to bind a compound having an ethylenic double bond to the compound.
  • the preferred range of the weight average molecular weight of these acrylyl resins measured by GPC is from 1,000 to 100,000. When the weight average molecular weight is less than 1,000 It is difficult to obtain a uniform coating film, and if it exceeds 100, 000, the developability tends to decrease.
  • the preferred content range of the carboxyl group is 5 to 200 in terms of acid value. If the acid value is 5 or less, it becomes insoluble in an alkali developer, and if it exceeds 200, the sensitivity may decrease.
  • binder resins are contained in the range of 10 to 80% by weight, preferably 20 to 70% by weight, based on the total solid content of the composition of the present invention.
  • the monomer contained in the composition for color filling according to the present invention is not particularly limited as long as it is a polymerizable low-molecular compound, and is a compound capable of addition polymerization having at least one ethylenic double bond.
  • ethylenic compound means that when the composition of the present invention is irradiated with actinic rays, it undergoes addition polymerization by the action of a photopolymerization initiation system (described later) and cures. It is a compound having such an ethylenic double bond.
  • the monomer in the present invention means a concept corresponding to a so-called polymer substance, and means a concept containing dimers, trimers, and oligomers in addition to monomers in a narrow sense.
  • Examples of the ethylenic compound include an unsaturated carboxylic acid, an ester thereof and a monohydroxy compound, an ester of an aliphatic polyhydroxy compound and an unsaturated carboxylic acid, an ester of an aromatic polyhydroxy compound and an unsaturated carboxylic acid, Ester, polyisocyanate compound obtained by esterification reaction between unsaturated carboxylic acid and polyvalent carboxylic acid and the above-mentioned polyvalent hydroxy compound such as aliphatic polyhydroxy compound and aromatic polyhydroxy compound, and (meth) Examples include an ethylenic compound having a urethane skeleton obtained by reacting an acryloyl-containing hydroxy compound.
  • ester of an aliphatic polyhydroxy compound and an unsaturated carboxylic acid examples include ethylene glycol diacrylate, triethylene glycol diacrylate, trimethylolpropane triacrylate, trimethylolethane triacrylate, and pentaerythritol diacrylate.
  • Acrylic acid esters such as phenol erythritol tetraacrylate, dipentyl erythritol tetraacrylate, dipentyl erythritol pen acrylate, dipentyl erythritol hexyl acrylate, and glycerol acrylate are listed.
  • acrylic acid portion of these acrylates is replaced with a methacrylic acid ester instead of the methacrylic acid portion, an itaconic acid ester replacing the itaconic acid portion, a crotonic acid ester replacing the clotonic acid portion, or a maleic acid portion.
  • a methacrylic acid ester instead of the methacrylic acid portion
  • an itaconic acid ester replacing the itaconic acid portion
  • a crotonic acid ester replacing the clotonic acid portion
  • maleic acid portion substituted maleic acid esters and the like can be mentioned.
  • ester of an aromatic polyhydroxy compound with an unsaturated carboxylic acid examples include hydroquinone diacrylate, quinone dimethacrylate, resorcin diacrylate, resorcin dimethacrylate, pyrogallol triacrylate, and the like.
  • the ester obtained by the esterification reaction of the unsaturated carboxylic acid with the polyhydric carboxylic acid and the polyhydric hydroxy compound is not necessarily a single substance, but may be a mixture.
  • Typical examples are condensates of acrylic acid, phthalic acid and ethylene glycol, condensates of acrylic acid, maleic acid and diethylene glycol, condensates of methyl methacrylate, telephthalic acid and erythritol pentane, acrylic acid, adipic acid And condensates of butanediol and glycerin.
  • Examples of the ethylenic compound having a urethane skeleton obtained by reacting a polyisocyanate compound with a (meth) acryloyl group-containing hydroxy compound include aliphatic disocyanates such as hexamethylene diisocyanate and trimethylhexamethylene diisocyanate; Aliphatic diisocyanates such as xanthyl diisocyanate and isophorone diisocyanate; aromatic diisocyanates such as tolylene diisocyanate and diphenyldimethyl diisocyanate; 2-hydroxyethyl acrylate; Such as 3-hydroxy (1,1,1-triacryloyloxymethyl) propane and 3-hydroxy (1,1,1-triacryloyloxymethyl) propane (Meth) acryloyl group-containing hydroxy compound Reactants are exemplified.
  • Other examples of the ethylenic compound used in the present invention include:
  • acrylamides such as rilamide
  • aryl esters such as diaryl fluorate
  • vinyl group-containing compounds such as divinyl phthalate.
  • the compounding ratio of these ethylenic compounds is 10 to 80% by weight, preferably 20 to 70% by weight, based on the total solid content of the composition of the present invention.
  • composition for color filling according to the present invention contains (b) an ethylenic compound as a monomer, it directly absorbs light or is photosensitized to cause a decomposition reaction or a hydrogen abstraction reaction, It is preferable to include a photopolymerization initiation system having a function of generating a polymerization active radical.
  • the photopolymerization initiation system used in the present invention is a system in which an additive such as an accelerator is used in combination with a polymerization initiator.
  • the polymerization initiator include, for example, a meta-mouth compound containing a chinocene compound described in JP-A-59-152396 and JP-A-6-151197.
  • Radical activators such as N-aryl-amino acid salts and N-aryl-amino acid esters.
  • Examples of the accelerator include N, N-dialkylamino benzoic acid alkyl esters such as N 5 N-dimethylaminobenzoic acid ester, 2-mercaptobenzothiazolyl, 2-mercaptobenzoxazole, and 2-mercaptobenzoxazodyl.
  • N N-dialkylamino benzoic acid alkyl esters such as N 5 N-dimethylaminobenzoic acid ester
  • 2-mercaptobenzothiazolyl such as 2-mercaptobenzoxazole
  • 2-mercaptobenzoxazodyl 2-mercaptobenzoxazodyl.
  • a mercapto compound having a heterocyclic ring or an aliphatic polyfunctional mercapto compound may be used.
  • the photopolymerization initiator and the additive may be used in combination of a plurality of types.
  • the compounding ratio of the photopolymerization initiation system is from 0.1 to 30% by weight, preferably from 0.5 to 20% by weight, more preferably from 0.7 to 10% by weight, based on the total solid content of the composition of the present invention. Duru. If the compounding ratio is extremely low, the sensitivity is lowered. On the other hand, if the mixing ratio is extremely high, the solubility of the unexposed portion in the developing solution is lowered, and poor development is easily induced. In the composition according to the present invention, if necessary, for the purpose of increasing the sensitivity, a sensitizing dye corresponding to the wavelength of the image exposure light source can be blended.
  • sensitizing dyes examples include the xanthene dyes described in JP-A-4-1221958 and JP-A-4-219756, and the complex described in JP-A-3-239703 and JP-A-5-289335.
  • dyes having a dialkylaminobenzene skeleton described in JP-A No. 77761, JP-A-5-210240 and JP-A No. 4-288818 can be used.
  • sensitizing dyes are amino group-containing sensitizing dyes, and more preferred are compounds having an amino group and a phenyl group in the same molecule.
  • the compounding ratio of the sensitizing dye is 0 to 20% by weight, preferably 0.2 to 15% by weight, more preferably 0.5 to 10% by weight based on the total solid content of the composition of the present invention.
  • the color filter composition according to the present invention may contain known pigments and dyes, if necessary, in addition to the specific phthalocyanine pigment described above. These pigments and dyes are added in accordance with the tint of the image to be formed, but the amount added is within a range that does not impair the high brightness and color purity, which are characteristics of the phthalocyanine pigment according to the present invention. Is preferred.
  • the mixing ratio of the entire coloring material in the composition is usually in the range of 1 to 70% by weight, preferably 1 to 60% by weight of the total solid components of the composition of the present invention.
  • the phthalocyanine pigment in addition to the phthalocyanine pigment represented by the general formula (1) or (2), the phthalocyanine pigment has a central metal other than Ga and has an arbitrary substituent.
  • a phthalocyanine pigment may be contained.
  • the phthalocyanine pigment represented by the general formula (1) or (2) has the above-described group as a substitution group, and the central metal is Cu, Ni, Co, Fe, Zn, Pd, Bivalent metals such as Mg, Ru, Rh, Pt, Mn, Ti, Be, Ca, Ba, Cd, Eg, Pb, Sn, Ag, Au; A1-X, In-X, T 1-X, Mn- X, F eX, substituted trivalent metal such Ru_X; S i- X 2, Ge -X 2, Sn- X 2, T i -X 23 Cr-X 25 Z rX 25 Mn- X Substituted trivalent metals such as 2 ; oxy metals such as VO, MnO and Tio; lanthanides.
  • Bivalent metals such as Mg, Ru, Rh, Pt, Mn, Ti, Be, Ca, Ba, Cd, Eg, Pb, Sn, Ag, Au
  • X represents a halogen atom, a hydroxyl group, an alkoxy group, an aryloxy group, or the like. More preferably Cu, N i, C o, F e, Z n, Pd, Mg 5 Al- X, I n - X, F eX, S i- X 2, Sn-X 2, T i- X 2, VO, TiO, and more preferably, Cu, Al—X, InX, and VO.
  • These phthalocyanine pigments may contain two or more kinds.
  • inorganic pigments such as barium sulfate, lead sulfate, titanium oxide, yellow lead, red iron oxide, chromium oxide, carbon black, and the like are used as pigments that can be used in the color filter composition of the present invention.
  • organic pigments include, for example, yellow pigments: C.I. pigment yellow 1, 3, 4, 5, 6, 12, 13, 14, 14, 16, 17, 18, 20, 24, 55, 65, 73, 74, 81, 83, 86, 87, 93, 94, 95, 97, 98, 100, 101, 108, 109, 110,
  • bioret pigments 240, 242 243, 245, 246, 247, 254; bioret pigments:
  • the dye examples include azo dyes, anthraquinone dyes, phthalocyanine dyes, quinonymine dyes, quinoline dyes, nitro dyes, carbonyl dyes, methine dyes, and the like.
  • azo dyes examples include C.I. Acid Yellow 11, C.I. Acid Orange 7, C.I. Acid Red 37, C.I. Acid Red 180, C.I. Acid Acid 180. Pull 1 29, C.I.Direct Red 28, C.I.Direct Red 83, C.I.Direct Toyero 1 12, C.I.Direct Orange 26, C.I.Direct Green 28, C.I. I. Direct Green 59, C. I. Reactive Yellow 2, C. I. Reactive Red 17, C. I. Reactive Red 120, C. I. Reactive Black 5, C. I. Disperse Orange 5, C.I. Disperse Red thread 58, C.I. Disperse Red 1 65, C.I. Basic Blue 41, C.I. Basic Cred 18, C.I. Mordant Red 7 , C.I. Moldantello I-5, C.I. Moldant Black 7, and the like.
  • anthraquinone-based dyes examples include C.I.Batpu-I-4, C.I.I.I.B.I.40, C.I.I.Aci. Green 25, C.I.I.Reactive Pro.19, C.I.R. Active Blue 49, CI Disperse Blade 60, CI Dispersible 1 56, CI Dispersible 1 60, and the like.
  • a phthalocyanine dye for example, C.I. Node Blue 5, etc.
  • a quinone imine dye for example, C.I. —Thick Blue 9 etc.
  • quinoline dyes for example CI Solvent Yellow 33
  • CI Acid Yellow 1 CI Disperse Yellow 64 etc. are nitro dyes, eg CI Acid Yellow 1, 1, CI Yellow CID Orange 3, CI Daispersiel Yellow 42 and the like.
  • the coloring material to be mixed with the phthalocyanine pigment according to the present invention is preferably a pigment.
  • composition for color filling according to the present invention may further contain, if necessary, a thermal polymerization inhibitor, a plasticizer, a storage stabilizer, a surface protective agent, a leveling agent, a coating aid and other additives.
  • thermal polymerization inhibitor for example, hydroquinone, ⁇ -methoxenol, pyrogallol, catechol, 2,6-t-butyl- ⁇ -cresol,? -Naphthol and the like are used.
  • the amount of the thermal polymerization inhibitor is preferably in the range of 0 to 3% by weight based on the total solid content of the composition.
  • plasticizer for example, dioctyl phthalate, didodecyl phthalate, triethylene glycol dicaprylate, dimethyl glycol phthalate, tricresinole phosphate, octyl adipate, dibutyl sebacate, triacetyl glycerin and the like are used.
  • the amount of these plasticizers is preferably in the range of 10% by weight or less based on the total solid content of the composition.
  • composition for color fill composition of the present invention may optionally contain an adhesion improver, a coatability improver, a development improver and the like.
  • the composition for a color filter according to the present invention is usually dissolved in a solvent in order to adjust the viscosity and dissolve additives such as a photopolymerization initiation system.
  • the solvent may be appropriately selected according to the components of the composition, such as (a) a binder resin and (b) a monomer, and various organic solvents such as an ether solvent can be used.
  • solvent examples include diisopropyl ether, mineral spirit, n- Pentane, amyl ether, ethyl caprylate, n-hexane, getyl ether, isoprene, ethyl isobutyl ether, butyl stearate, n-octane, balsol # 2, apco # 18 solvent, diisobutylene, Amyl acetate, butyl acetate, apco thinner, butyl ether, diisobutyl ketone, methylcyclohexene, methyl nonyl ketone, propyl ether, dodecane, sodium sorbent No. 1 and No.
  • composition for a color filter according to the present invention An example of the composition for a color filter according to the present invention and a method for producing a color filter using the composition will be described.
  • the color material is dispersed and adjusted to the ink state.
  • the dispersion treatment is performed using a paint conditioner, a sand grinder, a ball mill, a roll mill, a stone mill, a jet mill, a homogenizer, or the like. Since the coloring material is made into fine particles by the dispersion treatment, an improvement in transmittance of transmitted light and an improvement in coating characteristics are achieved.
  • the dispersing treatment is preferably performed in a system in which a binder resin having a dispersing function, a dispersant such as a surfactant, a dispersing aid, and the like are appropriately used in combination with a coloring material and a solvent.
  • a dispersant such as a surfactant, a dispersing aid, and the like
  • the dispersion treatment when the dispersion treatment is performed using a sand grinder, it is preferable to use glass beads or zirconia beads having a diameter of 0.1 to several millimeters.
  • the temperature at the time of the dispersion treatment is usually set in the range of 0 ° C to 100 ° C; preferably, in the range of room temperature to 80 ° C.
  • the appropriate dispersion time depends on the composition of the ink (colorant, solvent, dispersant), the size of the sand grinder, and the like, and must be adjusted accordingly.
  • the colored ink obtained by the dispersion treatment is mixed with a binder resin, a monomer, a photopolymerization initiation system, and the like to form a uniform solution.
  • fine dust is often mixed, so that the obtained solution is preferably subjected to a filtration treatment by a filter or the like.
  • the color filter according to the present invention can be usually manufactured by forming pixel images of red, green and blue on a transparent substrate provided with a black matrix.
  • the material of the transparent substrate is not particularly limited.
  • the material include thermoplastic resins such as polyester-polypropylene such as polyethylene terephthalate, polyolefin such as polyethylene, polycarbonate, polymethyl methacrylate, and polysulfone, epoxy resin, unsaturated polyester resin, and poly (Meth) Thermosetting plastics such as acrylic resin, or various glass plates. Among them, a glass plate and a heat-resistant plastic are preferable from the viewpoint of heat resistance.
  • the transparent substrate may be previously subjected to corona discharge treatment, ozone treatment, thin film treatment of various polymers such as silane coupling agent and urethane polymer, etc. to improve physical properties such as surface adhesiveness. .
  • the black matrix is formed on a transparent substrate using a metal thin film or a black matrix pigment dispersion.
  • a black matrix using a metal thin film is formed of, for example, a single layer of chromium or two layers of chromium and chromium oxide.
  • a thin film of these metals or metal / metal oxides is formed on a transparent substrate by vapor deposition or sputtering.
  • the photosensitive film is exposed and developed using a photomask having a repetitive pattern of stripes, mosaics, triangles, etc. to form a resist image.
  • the thin film is subjected to an etching process to form a black matrix.
  • a black matrix is formed using a photosensitive resin composition containing a black coloring material.
  • a black coloring material such as force pump rack, bone black, graphite, iron black, aniline black, cyanine black, titanium black, or the like, or an inorganic or organic pigment or dye are appropriately selected.
  • a rack matrix in the same manner as the method of forming the following red, green, and blue pixel images using the photosensitive resin composition.
  • a color filter composition containing one of red, green, and blue coloring materials is applied and dried, and then a photomask is placed on the composition, and A pixel image is formed by image exposure through a photomask, development, and, if necessary, by heat curing or light curing to form a colored layer. This operation is performed for each of the three color filter compositions of red, green (that is, the color filter composition of the present invention) and blue to form a color filter image.
  • the composition for color filling can be applied by a coating device such as a spinner, a wire bar, a flower, a die coater, a roll coater or a spray.
  • a coating device such as a spinner, a wire bar, a flower, a die coater, a roll coater or a spray.
  • Drying after application may be performed using a hot plate, an IR oven, a competition oven, or the like.
  • the drying temperature the higher the temperature, the better the adhesion to the transparent substrate.However, if the drying temperature is too high, the photopolymerization initiation system is decomposed, and thermal polymerization is apt to occur, resulting in poor development.
  • C preferably in the range of 50 to 150 ° C.
  • the drying time is in the range of 103 ⁇ 4 to 10 minutes, preferably 30 seconds to 5 minutes.
  • the film thickness of the composition for color filling after drying is in the range of 0.5 to 3111, preferably 1 to 2 ⁇ m.
  • the composition for color filling according to the present invention uses a binder resin and an ethylenic compound in combination, and the binder resin has an acrylyl-based resin having an ethylenic double bond and a hydroxyl group in a side chain.
  • this is very high sensitivity and high resolution, so that it is possible to form an image by exposing and developing without providing an oxygen barrier layer such as polyvinyl alcohol.
  • the exposure light source applicable to the composition for a color filter according to the present invention is not particularly limited.
  • Laser light sources such as a YAG laser, an excimer laser, a nitrogen laser, a helium force laser, and a semiconductor laser are used. If only a specific wavelength is used, an optical filter can be used.
  • composition for color-fill evening after performing image exposure with such a light source, if developed with an organic solvent or an aqueous solution containing a surfactant and an alkaline agent, on the substrate An image can be formed.
  • the aqueous solution may further contain an organic solvent, a buffer, a dye or a pigment.
  • the development processing method it is usually 10 to 50 ° C; preferably 15 to 45 ° C, and is preferably immersion development, spray development, brush development, ultrasonic development, or the like. A method is used.
  • alkaline agent examples include inorganic alkalis such as sodium silicate, potassium silicate, sodium hydroxide, water oxidizing lime, lithium hydroxide, tribasic sodium phosphate, dibasic sodium phosphate, sodium carbonate, potassium carbonate, and sodium bicarbonate.
  • organic amines such as trimethylamine, getylamine, isopropylamine, n-butylamine, monoethanolamine, jetanolamine, triethanolamine, and tetraalkylammonium hydroxide. These can be used alone or in combination.
  • surfactant examples include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl esters, sorbin alkyl esters, and monoglyceride alkyl esters.
  • Activators such as alkyl benzene sulfonates, alkyl naphthalene sulfonates, alkyl sulfates, alkyl sulfonates, sulfosuccinates
  • amphoteric surfactants such as alkyl betaines and amino acids; Can be used.
  • the organic solvent may be used alone or in combination with an aqueous solution, for example, isopropyl alcohol, benzyl alcohol, ethyl ethyl solvent, butyl cellosolve, phenolic acid solvent, propylene glycol, diacetone alcohol, etc. Can be used.
  • the color filter of the present invention can be manufactured by a method of applying a polyimide resin composition containing the phthalocyanine pigment and forming a pixel image by an etching method, in addition to the above method. Further, a method of forming a pixel image directly on a transparent substrate by a printing machine using the resin composition containing the phthalocyanine pigment as a coloring ink, or immersing the resin composition in the electrodeposition liquid comprising the resin composition containing the phthalocyanine pigment It can also be manufactured by a method of depositing a colored film on the ITO electrode having a predetermined pattern.
  • a method in which a film coated with the resin composition containing the phthalocyanine pigment is adhered to a transparent substrate, peeled off, image exposed and developed to form a pixel image, or an ink using the ink containing the phthalocyanine pigment described above can also be manufactured by a method of forming a pixel image image by using an etrin pudding.
  • the production method used is more suitable for the composition of the color filter composition.
  • a phthalocyanine-based compound containing Ga C 1-hexaclo-methoxyphthalocyanine represented by the following formula was obtained. This compound was dispersed in 285 volumes of 95% concentrated sulfuric acid, stirred for 6 hours, poured into ice water of 10 volumes of concentrated sulfuric acid, and the precipitated crystals were collected by filtration, washed with water and dried to form a pigment. went.
  • the structure of the manufactured phthalocyanine compound was confirmed by IR spectrum and MAS S spectrum.
  • the IR spectrum was measured using Horiba Seisakusho FT-IR FT-210.
  • the MAS S spectrum was measured by the DCI method (+) and (1) (apparatus used: JMS-700 manufactured by JEOL (JEOL)). The results are shown in FIGS. Production Example 4
  • This compound was dispersed in 285 volumes of 95% concentrated sulfuric acid, stirred for 6 hours, poured into ice water of 10 volumes of concentrated sulfuric acid, and the precipitated crystals were collected by filtration, washed with water, and dried to form a pigment. Was done.
  • the structure of the manufactured phthalocyanine compound was confirmed by IR spectrum and MAS S spectrum.
  • the IR spectrum was measured using Horiba Seisakusho; FT-IR FT-210.
  • the MAS S spectrum was measured by the DCI method (+) and (1) (using equipment: JMS-700 manufactured by JEOL (JEOL)). The results are shown in FIGS. Production Example 5
  • the precipitate is collected by filtration, washed with methanol, N-methylpyrrolidone, and methanol in that order, dried, and a phthalocyanine compound containing GaC 1-hexachloro-sulfofucyanine represented by the formula (19). 4.56 g were obtained.
  • This compound was dispersed in 285 volumes of 95% concentrated sulfuric acid, stirred for 6 hours, poured into ice water of 10 volumes of concentrated sulfuric acid, and the precipitated crystals were collected by filtration, washed with water, and dried to form a pigment. went.
  • the obtained dispersion ink was applied to a glass substrate (AN 635, manufactured by Asahi Glass Co., Ltd.) using a spinco overnight to form a sample.
  • a glass substrate AN 635, manufactured by Asahi Glass Co., Ltd.
  • Styrene / acrylic acid resin with acid value 200, weight average molecular weight 5,000 20 parts, P-methoxyphenol 0.2 parts, dodecyl trimethylammonium chloride 0.2 parts, and propylene glycol monomethyl ether acetate 40 parts were charged into a flask, 7.6 parts of (3,4-epoxycyclohexyl) methyl acrylate was added dropwise, and reacted at a temperature of 100 ° C for 30 hours. The reaction solution was reprecipitated in water and dried to obtain a resin. As a result of neutralization titration with KOH, the acid value of the resin was 8 OmgKO H / g. Production Example 8 (Preparation of green colorant dispersed ink)
  • the obtained dispersion ink was applied to a glass substrate (AN 635, manufactured by Asahi Glass Co., Ltd.) using a spinco overnight to form a sample.
  • a glass substrate AN 635, manufactured by Asahi Glass Co., Ltd.
  • a dispersion having a solid content of 8% by weight was well mixed with a stirrer and premixed. Next, a dispersion treatment was performed for 5 hours in a temperature range of 25 to 45 ° C by a paint shear. As the beads, 20 parts of 0.5 mm0 zirconia beads were used. After the dispersion, the beads were removed by filtration to obtain a dispersed ink.
  • the obtained dispersion ink was applied to a glass substrate (AN 635, manufactured by Asahi Glass Co., Ltd.) using a spinner overnight to form a sample.
  • AN 635 manufactured by Asahi Glass Co., Ltd.
  • the maximum transmittance wavelength was 513 im. Comparative Reference Example 2
  • Pigment Green 36 as a green pigment (no acid slurry treatment) 0.5
  • a sample was prepared and evaluated in the same manner as in Reference Example 10 except that the part was used.
  • the maximum transmittance wavelength was 512 nm, and the maximum transmittance wavelength was shorter than in Reference Example 10.
  • Production Example 14 (Preparation of green colorant-dispersed ink 1)
  • Pigment Green 369.0 parts 1.0 part of the GaCl-octyl chlorophthalocyanine obtained in Production Example 13, 30% by weight of the polymer dispersing agent BYK 161 (trade name, manufactured by BYK Chemie)
  • a dispersion was prepared by adding 33.4 parts of a propylene glycol monomethyl ether acetate (PGMEA) solution and 33.3 parts of PGMEA as a solvent.
  • PGMEA propylene glycol monomethyl ether acetate
  • PGMEA propylene glycol monomethyl ether acetate
  • a green colorant-dispersed ink 2 was obtained in the same manner as in Production Example 14, except that the above-mentioned acid paste-treated Gac1-octachlorofluorocysteine was used instead of GaC 1-octachlorofluorocysteine obtained in Production Example 13.
  • Production Example 16 (Preparation of green color material dispersion ink 3)
  • a green colorant-dispersed ink 3 was obtained in the same manner as in Production Example 14 except that the above V0PcCl 16 was used instead of GaC 1 -octachlorofurocyanine obtained in Production Example 13.
  • Production Example 17 (Preparation of green colorant-dispersed ink 4)
  • a green colorant-dispersed ink 4 was obtained in the same manner as in Production Example 14, except that the above NiPcCl 16 was used in place of G aC 1-octachlorofurocyanine obtained in Production Example 13.
  • Production Example 18 (Preparation of comparative green coloring material dispersed ink 1)
  • a comparative green colorant-dispersed ink 1 was obtained in the same manner as in Production Example 14 except that only Pigment Green 36 10.0 parts was used as the pigment.
  • Example 3 A comparative green colorant-dispersed ink 1 was obtained in the same manner as in Production Example 14 except that only Pigment Green 36 10.0 parts was used as the pigment.
  • Samples 2 to 2 of green pixels were prepared in the same manner as in Example 3 except that the colorant-dispersed inks 2 to 4 obtained in Production Examples 15 to 18 and the green-dispersion ink 1 for comparative example were used as the colorant-dispersed inks. 5 was produced.
  • Table 11 shows the maximum transmittance wavelength of this sample.
  • Pigment Yellow 138 (8.0 parts), BYK-182 (Big Chemical Co., Inc. high molecular dispersant) 8.0 parts, and propylene glycol monomethyl ether acetate (1.52 parts) were added to prepare a dispersion.
  • the dispersion was stirred with a stirrer to perform premixing.
  • a dispersion treatment was performed for 6 hours in a temperature range of 25 to 45 ° C by a paint shear. Zirconia beads of 0.5 mm ⁇ as beads were added in the same weight as the dispersion. After the dispersion, the beads were removed by filtration to obtain a dispersion ink.
  • Example 7 Example 7
  • composition for color filters and color filters of the present invention can provide a high brightness color filter composition by using a specific fluorinated cyanine-based compound.

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Abstract

L'invention concerne une composition de filtres colorés comprenant une matière colorante et une résine liante et/ou un monomère. Cette composition est caractérisée en ce qu'elle contient en tant que matière colorante au moins un pigment de phtalocyanine représenté par la formule générale (1) ou (2) : (1) . (Au moins quatre des symboles X1 à X16 représentent chacun individuellement halogéno et les éléments restants représentent chacun un substituant arbitraire comprenant l'hydrogène, et M est Ga-Z, Z représentant un substituant arbitraire). (2) (au moins quatre élément de X1 à X16 et au moins quatre des symboles X17 à X32 représentent chacun individuellement halogéno, et les éléments restants sont chacun individuellement un substituant arbitraire comprenant l'hydrogène, et M représente Ga).
PCT/JP2001/006988 2000-08-17 2001-08-13 Composition de filtres colores et filtres colores WO2002014912A1 (fr)

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WO2004010172A1 (fr) * 2002-07-24 2004-01-29 Dai Nippon Printing Co., Ltd. Pigment vert pour filtre colore, dispersion de pigment vert, composition coloree photosensible, filtre colore, et panneau a cristaux liquides
US6826001B2 (en) 2001-02-23 2004-11-30 Dainippon Ink And Chemicals, Inc. Color filter
WO2010053503A3 (fr) * 2008-10-29 2010-11-04 Global Oled Technology Llc. Élément de filtre coloré à dispersion de colorant améliorée

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US6716897B2 (en) * 2000-12-22 2004-04-06 Toyo Ink Mfg. Co., Ltd. Colored composition for color filter and color filter
KR101573937B1 (ko) * 2009-07-02 2015-12-03 동우 화인켐 주식회사 초단파장 노광기를 이용한 고체 촬상 소자용 컬러 필터의 제조방법, 그 방법에 의해 제조된 컬러 필터 및 이를 포함하는 고체 촬상 소자

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JPH1030064A (ja) * 1996-05-17 1998-02-03 Fuji Xerox Co Ltd 電子吸引性基含有ヒドロキシガリウムフタロシアニン結晶及びそれを用いる電子写真感光体
EP0833203A1 (fr) * 1996-09-30 1998-04-01 Nippon Shokubai Co., Ltd. Composition à base de résine photosensible pour filtre-couleur et filtre-couleur fabriqué avec cette composition
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US4793692A (en) * 1984-12-14 1988-12-27 Canon Kabushiki Kaisha Color filter
EP0519423A2 (fr) * 1991-06-19 1992-12-23 MITSUI TOATSU CHEMICALS, Inc. Composés de phthalocyanine et leur utilisation
US5759726A (en) * 1996-01-17 1998-06-02 Fuji Xerox Co., Ltd. Electrographic photosensitive member
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Publication number Priority date Publication date Assignee Title
US6826001B2 (en) 2001-02-23 2004-11-30 Dainippon Ink And Chemicals, Inc. Color filter
WO2004010172A1 (fr) * 2002-07-24 2004-01-29 Dai Nippon Printing Co., Ltd. Pigment vert pour filtre colore, dispersion de pigment vert, composition coloree photosensible, filtre colore, et panneau a cristaux liquides
US7781129B2 (en) 2002-07-24 2010-08-24 Dai Nippon Printing Co., Ltd. Green pigment for color filter, green pigment dispersion, photosensitive color composition, color filter, and liquid crystal panel
US8211599B2 (en) 2002-07-24 2012-07-03 Dai Nippon Printing Co., Ltd. Green pigment for color filter, green pigment dispersion, photosensitive color composition, color filter, and liquid crystal panel
WO2010053503A3 (fr) * 2008-10-29 2010-11-04 Global Oled Technology Llc. Élément de filtre coloré à dispersion de colorant améliorée
US8277697B2 (en) 2008-10-29 2012-10-02 Global Oled Technology Llc Color filter element with improved colorant dispersion

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