WO2014196464A1 - Composition colorée photosensible et nouveau composé - Google Patents

Composition colorée photosensible et nouveau composé Download PDF

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Publication number
WO2014196464A1
WO2014196464A1 PCT/JP2014/064411 JP2014064411W WO2014196464A1 WO 2014196464 A1 WO2014196464 A1 WO 2014196464A1 JP 2014064411 W JP2014064411 W JP 2014064411W WO 2014196464 A1 WO2014196464 A1 WO 2014196464A1
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WIPO (PCT)
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group
atom
carbon atoms
substituted
halogen atom
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PCT/JP2014/064411
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English (en)
Japanese (ja)
Inventor
裕介 久保田
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株式会社Adeka
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Priority to KR1020157016275A priority Critical patent/KR102229645B1/ko
Priority to CN201480003605.4A priority patent/CN104871045B/zh
Priority to JP2015521423A priority patent/JP6417323B2/ja
Publication of WO2014196464A1 publication Critical patent/WO2014196464A1/fr

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Classifications

    • 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
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
    • 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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
    • C09B69/06—Dyestuff salts, e.g. salts of acid dyes with basic dyes of cationic dyes with organic acids or with inorganic complex acids
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

Definitions

  • the present invention relates to a colored photosensitive composition that can be polymerized by energy rays, and a color filter that uses the colored photosensitive composition, and a dye that is designed to have a desired hue and has improved solubility and heat resistance.
  • the present invention relates to a novel compound suitable for a dye.
  • Compounds having high intensity absorption for specific light include recording layers of optical recording media such as CD-R, DVD-R, DVD + R, BD-R, liquid crystal display (LCD), plasma display panel (PDP) ), An electroluminescence display (ELD), a cathode ray tube display (CRT), a fluorescent display tube, and an optical display element such as a field emission display.
  • optical recording media such as CD-R, DVD-R, DVD + R, BD-R, liquid crystal display (LCD), plasma display panel (PDP) ), An electroluminescence display (ELD), a cathode ray tube display (CRT), a fluorescent display tube, and an optical display element such as a field emission display.
  • an optical filter for an image display device such as a liquid crystal display device (LCD), a plasma display panel (PDP), an electroluminescence display (ELD), a cathode ray tube display device (CRT), a fluorescent display tube, a field emission display, etc.
  • Various compounds that absorb light having a wavelength of ⁇ 1100 nm are used as light absorbers. These light absorbers are required to have particularly steep light absorption, that is, having a small half-value width of ⁇ max and not to lose its function due to light, heat, or the like.
  • An optical filter mainly used for a liquid crystal display includes a color filter.
  • three primary colors of RGB have been used for a color filter, but it is difficult to have a pure RGB hue with a single color material, and a pure RGB hue using a plurality of color materials. Efforts have been made to get closer to. Therefore, color materials such as yellow, orange and purple are required instead of RGB.
  • Organic and / or inorganic pigments have been used as light absorbers for color filters due to their high heat resistance. However, since they are pigments, there is a problem in that the luminance of a display device is lowered. This problem has been solved by increasing the brightness of the. However, with the trend toward lower power consumption, development of color filters using dyes has become active.
  • Patent Documents 1 and 2 disclose a colored resin composition for a color filter containing a triarylmethane dye having a specific structure
  • Patent Document 4 discloses a triarylmethane dye having a polymerizable group in an anion.
  • a photosensitive coloring composition containing a monomer is disclosed.
  • the triarylmethane dyes described in these documents are not satisfactory in terms of heat resistance.
  • Patent Document 3 discloses a xanthylium salt useful for medical use, but there is no description or suggestion that the xanthylium salt can be used in a colored photosensitive composition for a color filter.
  • an object of the present invention is to provide a colored photosensitive composition (colored alkali-developable photosensitive composition) using the above dye.
  • Another object of the present invention is an optical filter using the colored photosensitive composition (colored alkali-developable photosensitive composition), particularly suitable for an image display device such as a liquid crystal display panel without reducing luminance. It is to provide a color filter.
  • Another object of the present invention is to provide a novel compound suitable for a dye having excellent solubility and heat resistance.
  • the present inventor has found that a compound having a specific structure is excellent in heat resistance and excellent in solubility in a colored photosensitive composition (colored alkali-developable photosensitive composition).
  • the colored photosensitive composition (colored alkali-developable photosensitive composition) does not decrease the luminance of the optical filter (particularly the color filter) and is suitable for a color filter for an image display device such as a liquid crystal display panel.
  • the present invention has been made on the basis of the above findings, and is a dye (A) comprising a compound represented by the following general formula (I), a polymerizable compound (B) having an ethylenically unsaturated bond, and a photopolymerization initiator ( A colored photosensitive composition containing C) is provided.
  • a dye (A) comprising a compound represented by the following general formula (I), a polymerizable compound (B) having an ethylenically unsaturated bond, and a photopolymerization initiator ( A colored photosensitive composition containing C) is provided.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 are each independently a hydrogen atom, a halogen atom, a cyano group, or a nitro group.
  • R 11 , R 12 , R 13 , R 14 , R 15 and R 16 each independently represent a hydroxyl group, a halogen atom, a cyano group or a nitro group, A cyano group, a nitro group, a hydroxyl group or a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms
  • Substituted with an alkyl group having 1 to 4 carbon atoms, a halogen atom, a cyano group or a vinyl group, or an unsubstituted phenyl group or an alkyl group having 1 to 4 carbon atoms, a halogen atom, a cyano group or a vinyl group Represents an unsubstituted
  • R 11 and R 12 , R 13 and R 14 , and R 15 and R 16 may be linked to form a 3- to 6-membered heterocyclic ring
  • R 3 and R 4 and R 7 and R 8 are linked via a single bond, oxygen atom, sulfur atom, selenium atom, CR 17 R 18 , CO, NR 19 , PR 20 or SO 2 to form a ring.
  • R 4 and R 5 , R 6 and R 7 may be linked to form a 6-membered ring
  • X represents a single bond, an oxygen atom, a sulfur atom, a selenium atom, CR 17 R 18 , CO, NR 19 , PR 20 or SO 2
  • R 17 and R 18 are each independently a hydrogen atom, a halogen atom, or an unsubstituted alkyl group having 1 to 8 carbon atoms, a halogen atom, or an unsubstituted carbon atom of 1
  • R 19 and R 20 each independently represents a hydrogen atom, a halogen atom-substituted or unsubstituted alkyl group having 1 to 8 carbon atoms
  • An q ⁇ represents a q-valent anion
  • q represents 1 or 2
  • p represents a coefficient for keeping the charge neutral.
  • the present invention also provides a colored alkali-developable photosensitive composition containing the dye (A), an alkali-developable polymerizable compound (B ′) having an ethylenically unsaturated bond, and a photopolymerization initiator (C). It provides things.
  • the present invention also provides a cured product of the colored photosensitive composition or the colored alkali-developable photosensitive composition and a color filter for a display device using the cured product.
  • the present invention provides a compound represented by the following general formula (II).
  • R 1 ′ , R 2 ′ , R 3 ′ , R 4 ′ , R 5 ′ , R 6 ′ , R 7 ′ , R 8 ′ , R 9 ′ and R 10 ′ are each independently hydrogen Represents an atom, halogen atom, cyano group, nitro group or hydroxyl group
  • R 11 ′ , R 12 ′ , R 13 ′ , R 14 ′ , R 15 ′ and R 16 ′ each independently represent a hydroxyl group, a halogen atom, a cyano group or a nitro group, A cyano group, a nitro group, a hydroxyl group or a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms
  • R 11 ′ and R 12 ′ , R 13 ′ and R 14 ′ , and R 15 ′ and R 16 ′ may be linked to form a 3- to 6-membered heterocyclic ring
  • R 3 ′ and R 4 ′ and R 7 ′ and R 8 ′ are each bonded via a single bond, oxygen atom, sulfur atom, selenium atom, CR 17 ′ R 18 ′ , CO, NR 19 ′ , PR 20 or SO 2.
  • R 4 ′ and R 5 ′ , R 6 ′ and R 7 ′ may be linked to form a 6-membered ring
  • X ′ represents a single bond, oxygen atom, sulfur atom, selenium atom, CR 17 ′ R 18 ′ , CO, NR 19 ′ , PR 20 ′ or SO 2
  • R 17 ′ and R 18 ′ each independently represent a hydrogen atom, a halogen atom-substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, or a halogen atom-substituted or unsubstituted carbon atom.
  • R 19 ′ and R 20 ′ each independently represent a hydrogen atom, a halogen atom-substituted or unsubstituted alkyl group having 1 to 8 carbon atoms
  • An q ⁇ represents a q-valent anion
  • q represents 1 or 2
  • p represents a coefficient for keeping the charge neutral.
  • at least one of R 1 ′ , R 2 ′ , R 3 ′ , R 4 ′ , R 5 ′ , R 6 ′ , R 7 ′ , R 8 ′ , R 9 ′ and R 10 ′ is a hydrogen atom. Not. )
  • the colored photosensitive composition and colored alkali-developable photosensitive composition of the present invention containing a compound having a specific structure are excellent in solubility and heat resistance. .
  • the cured product is suitable for a color filter for a display device.
  • the coloring composition of the present invention comprises a dye (A) (hereinafter also referred to as a dye (A)) comprising at least one compound represented by the general formula (I), a polymerizable compound having an ethylenically unsaturated bond ( B) (including a polymerizable compound (B ′) having an ethylenically unsaturated bond having an alkali-soluble substituent that gives alkali developability), a photopolymerization initiator (C), and a colorant (if necessary)
  • a dye (A) comprising at least one compound represented by the general formula (I), a polymerizable compound having an ethylenically unsaturated bond ( B) (including a polymerizable compound (B ′) having an ethylenically unsaturated bond having an alkali-soluble substituent that gives alkali developability), a photopolymerization initiator (C), and a colorant (if necessary)
  • B including a polymerizable compound having
  • the dye (A) used in the present invention only needs to contain at least one compound represented by the above general formula (I), and can be used alone or in combination.
  • a known dye can be used as the dye (A).
  • Known dyes include, for example, azo dyes, anthraquinone dyes, indigoid dyes, triarylmethane dyes, xanthene dyes, alizarin dyes, acridine dyes, stilbene dyes, thiazole dyes, naphthol dyes, quinoline dyes, nitro dyes, indamine dyes, oxazine dyes. , Phthalocyanine dyes, cyanine dyes, and the like. These may be used in combination.
  • Examples of the alkyl group having 1 to 8 atoms include methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl, iso-amyl, tert-amyl, hexyl and 2-hexyl.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 and R 16 and X are R 17 and R 18 when represented by CR 17 R 18 , R 19 when X is represented by NR 19 , a cyano group represented by R 20 when X is represented by PR 20 , a nitro group, a hydroxyl group, As the alkyl group having 1 to 8 carbon atoms substituted with a halogen atom, part or all of the hydrogen atoms in the above alkyl group having 1 to 8 carbon atoms are cyano group, nitro group, hydroxyl group, halogen atom A group substituted with R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 and when X is represented by CR 17 R 18 , R 17 and
  • R 1 and R 11 , R 2 and R 12 , R 5 and R 13 , R 6 and R 14 , R 9 and R 15, and R 10 and R 16 may be linked together.
  • the 6-membered ring include a piperidine ring, a pyridine ring, a pyrimidine ring, a quinoline ring, and an isoquinoline ring.
  • Examples of the 3- to 6-membered heterocyclic ring that can be formed by linking R 11 and R 12 , R 13 and R 14 , and R 15 and R 16 include a piperidine ring, piperazine ring, pyrrolidine ring, morpholine ring, thiol Examples include morpholine ring, pyridine ring, pyrazine ring, pyrimidine ring, quinoline ring, isoquinoline ring, imidazole ring, oxazole ring, imidazolidine ring, pyrazolidine ring, isoxazolidine ring, isothiazolidine ring and the like.
  • the 6-membered ring that can be formed by linking R 4 and R 5 , R 6 and R 7 includes a benzene ring, These rings may be condensed or substituted with other rings.
  • Examples of the anion represented by An q- in the general formula (I) include monovalent and divalent ones.
  • monovalent ones include halide ions such as chloride ion, bromide ion, iodide ion and fluoride ion; perchlorate ion, chlorate ion, thiocyanate ion, hexafluorophosphate ion, hexafluoroantimony Inorganic anions such as acid ions and tetrafluoroborate ions; methanesulfonate ions, dodecylsulfonate ions, benzenesulfonate ions, toluenesulfonate ions, trifluoromethanesulfonate ions, naphthalenesulfonate ions, diphenylamine-4- Sulfonate ion, 2-amino-4-methyl-5-chlorobenzenesulfonate ion, 2-a
  • Organic sulfonate anions such as sulfonate ions described in the above; octyl phosphate ion, dodecyl phosphate ion, octadecyl phosphate ion, phenyl phosphate ion, nonylphenyl phosphate ion, 2,2′-methylenebis (4 6-di-t-butylphenyl) phosphonate ion
  • Organophosphate anions bistrifluoromethylsulfonylimide ion, bisperfluorobutanesulfonylimide ion, perfluoro-4-ethylcyclohexanesulfonate ion, tetrakis (pentafluorophenyl) borate ion, tris (fluoroalkylsulfonyl) Carbanion etc.
  • a benzene disulfonic acid ion, a naphthalene disulfonic acid ion, etc. are mentioned, for example.
  • quencher anions that have the function of deexciting (quenching) active molecules in the excited state
  • ferrocenes having an anionic group such as a carboxyl group, phosphonic acid group, or sulfonic acid group on the cyclopentadienyl ring.
  • Metallocene compound anions such as luteocene can also be used as necessary.
  • p is selected so that the charge is neutral throughout the molecule.
  • quencher anion examples include, for example, JP-A-60-234892, JP-A-5-43814, JP-A-5-305770, JP-A-6-239028, JP-A-9-309886.
  • Examples of the anion represented by An q- in the general formula (I) include a monovalent organic sulfonic acid anion, bistrifluoromethylsulfonylimide ion, bisperfluorobutanesulfonylimide ion, perfluoro-4- Ethylcyclohexanesulfonate ion, benzenedisulfonate ion, and naphthalenedisulfonate ion are preferable from the viewpoint of heat resistance, and bistrifluoromethylsulfonylimide ion is more preferable.
  • R 11 , R 12 , R 13 , R 14 , R 15 and R 16 are each a polar group, particularly an alkyl group having 1 to 8 carbon atoms substituted or unsubstituted with a hydroxyl group from the viewpoint of solvent solubility.
  • X is preferably an oxygen atom or a sulfur atom from the viewpoint of availability.
  • the manufacturing method of the compound represented with the said general formula (I) is not specifically limited, For example, when X in the said general formula (I) is an oxygen atom, it can manufacture according to following Reaction Formula. In addition, also when X is other than an oxygen atom, it can manufacture according to the following manufacturing method. It can also be produced according to known methods described in Journal of Organic Chemistry (2009), 74 (8), 3183-3185.
  • the compound represented by the general formula (I) can be used singly or in combination, and the total content is preferably in the dye (A). Is 50 to 100% by mass, more preferably 70 to 100% by mass. When the content of the compound represented by the general formula (I) of the present invention is less than 50% by mass, the solubility in a solvent may be lowered, or the heat resistance may be lowered.
  • the content of the dye (A) in the colored composition of the present invention is preferably 0.01 to 50% by mass, more preferably 0.1 to 30% by mass. If the content of the dye (A) is less than 0.01% by mass, a color having a desired concentration may not be obtained in the cured product of the colored composition of the present invention. In some cases, precipitation of the dye (A) may occur.
  • the polymerizable compound (B) having an ethylenically unsaturated bond is not particularly limited, and those conventionally used in photosensitive compositions can be used.
  • ethylene, propylene, butylene, isobutylene can be used.
  • Unsaturated polybasic acids such as polyfunctional (meth) acrylates; 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, glycidyl (meth) acrylate; A1-No.
  • A4 methyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, cyclohexyl (meth) acrylate, n-octyl (meth) acrylate, ( Isooctyl (meth) acrylate, isononyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, methoxyethyl (meth) acrylate, dimethylaminomethyl (meth) acrylate, dimethyl (meth) acrylate Aminoethyl, aminopropyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, ethoxyethyl (meth) acrylate, poly (ethoxy) ethyl (meth) acrylate, butoxyethoxyethyl (
  • polymerizable compounds can be used alone or in admixture of two or more, and when used in admixture of two or more, they are copolymerized in advance and used as a copolymer. May be.
  • the colored composition of the present invention as the polymerizable compound (B) having an ethylenically unsaturated bond, a polymerizable compound (B) having an ethylenically unsaturated bond having an alkali-soluble substituent that imparts alkali developability.
  • a polymerizable compound (B) having an ethylenically unsaturated bond having an alkali-soluble substituent that imparts alkali developability When ') (hereinafter also referred to as an alkali-developable compound (B') having an ethylenically unsaturated bond) is used, the colored photosensitive composition of the present invention becomes a colored alkaline-developable photosensitive composition.
  • alkali-developable compound (B ′) having an ethylenically unsaturated bond examples include (meth) acrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, Butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, benzyl (meth) acrylate, phenyl (meth) acrylate, cyclohexyl (meth) acrylate, phenoxyethyl (meth) acrylate, 2-ethylhexyl ( (Meth) acrylates such as (meth) acrylate, isobornyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate; N-vinylpyrroli
  • a copolymer of (meth) acrylic acid, and an isocyanate compound having an unsaturated bond such as Karenz MOI and AOI manufactured by Showa Denko K.K.
  • a polyphenylmethane type epoxy resin having a functional epoxy group, obtained by reacting an unsaturated monobasic acid with an epoxy group such as an epoxy compound represented by the following general formula (III), and further reacting with a polybasic acid anhydride Resins can be used. These monomers can be used individually by 1 type or in mixture of 2 or more types.
  • the alkali developable compound (B ′) having an ethylenically unsaturated bond preferably contains
  • X 1 is a direct bond, a methylene group, an alkylidene group having 1 to 4 carbon atoms, an alicyclic hydrocarbon group having 3 to 20 carbon atoms, —O—, —S—, —SO 2 —, —SS—, —SO—, —CO—, —OCO—, or a substituent represented by the following formula (A), (B) or (C), wherein the alkylidene group may be substituted with a halogen atom
  • R 31 , R 32 , R 33 and R 34 are each independently a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, or an alkenyl having 2 to 5 carbon atoms. Represents a group or a halogen atom, and the alkyl group, alkoxy group and alkenyl group may be substituted with a halogen atom, and m is an integer of 0 to 10.
  • Y 2 represents a phenyl group which may be substituted by an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, or 1 carbon atom
  • Y 1 represents an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms.
  • alkenyl group having 2 to 10 carbon atoms or a halogen atom the alkyl group, alkoxy group and alkenyl group in Y 1 may be substituted with a halogen atom, and b is an integer of 0 to 5.
  • Y 3 and Y 4 are each independently an alkyl group having 1 to 10 carbon atoms which may be substituted with a halogen atom, or an aryl having 6 to 20 carbon atoms which may be substituted with a halogen atom.
  • Examples of the unsaturated monobasic acid that acts on the epoxy group of the epoxy compound include acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, sorbic acid, hydroxyethyl methacrylate / malate, and the like. Examples thereof include hydroxyethyl acrylate / malate, hydroxypropyl methacrylate / malate, hydroxypropyl acrylate / malate, and dicyclopentadiene / malate.
  • the polybasic acid anhydride to be acted after the unsaturated monobasic acid is allowed to act is biphenyltetracarboxylic dianhydride, tetrahydrophthalic anhydride, succinic anhydride, maleic anhydride, trimellitic anhydride , Pyromellitic anhydride, 2,2'-3,3'-benzophenone tetracarboxylic anhydride, ethylene glycol bisanhydro trimellitate, glycerol tris anhydro trimellitate, hexahydro phthalic anhydride, methyl tetrahydro phthalic anhydride Acid, nadic anhydride, methyl nadic anhydride, trialkyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, 5- (2,5-dioxotetrahydrofuryl) -3-methyl-3-cyclohexene-1,2- Dicarboxylic anhydride, trialkyltetra
  • the reaction molar ratio of the epoxy compound, the unsaturated monobasic acid and the polybasic acid anhydride is preferably as follows. That is, in an epoxy adduct having a structure in which 0.1 to 1.0 carboxyl groups of the unsaturated monobasic acid are added to one epoxy group of the epoxy compound, the hydroxyl group 1 of the epoxy adduct is It is preferable that the ratio of the acid anhydride structure of the polybasic acid anhydride is 0.1 to 1.0. Reaction of the said epoxy compound, the said unsaturated monobasic acid, and the said polybasic acid anhydride can be performed in accordance with a conventional method.
  • a monofunctional or polyfunctional epoxy compound may be used together with the alkali-developable compound having an ethylenically unsaturated bond. It can.
  • the alkali-developable compound having an ethylenically unsaturated bond preferably has a solid content acid value in the range of 5 to 120 mgKOH / g, and the use amount of the monofunctional or polyfunctional epoxy compound satisfies the acid value. It is preferable to select as follows.
  • Examples of the monofunctional epoxy compound include glycidyl methacrylate, methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butyl glycidyl ether, isobutyl glycidyl ether, t-butyl glycidyl ether, pentyl glycidyl ether, hexyl glycidyl ether, heptyl Glycidyl ether, octyl glycidyl ether, nonyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, pentadecy
  • the polyfunctional epoxy compound it is preferable to use one or more selected from the group consisting of bisphenol-type epoxy compounds and glycidyl ethers as the polyfunctional epoxy compound because a colored alkali-developable photosensitive composition with better characteristics can be obtained.
  • the bisphenol type epoxy compound an epoxy compound represented by the above general formula (III) can be used, and for example, a bisphenol type epoxy compound such as a hydrogenated bisphenol type epoxy compound can also be used.
  • glycidyl ethers examples include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,8-octanediol diglycidyl ether, 1 , 10-decanediol diglycidyl ether, 2,2-dimethyl-1,3-propanediol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, hexaethylene glycol diglycidyl ether 1,4-cyclohexanedimethanol diglycidyl ether, 1,1,1-tri (glycidyloxymethyl) propane, 1,1,1-tri (g Glycidyl oxymethyl) ethane, 1,1,1-tri (g
  • novolac epoxy compounds such as phenol novolac epoxy compounds, biphenyl novolac epoxy compounds, cresol novolac epoxy compounds, bisphenol A novolac epoxy compounds, dicyclopentadiene novolac epoxy compounds; 3,4-epoxy-6-methyl Cycloaliphatic epoxy such as cyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 1-epoxyethyl-3,4-epoxycyclohexane Compound: Glycidyl esters such as diglycidyl phthalate, diglycidyl tetrahydrophthalate, glycidyl dimer, tetraglycidyl diamino Glycidylamines such as phenylmethane, triglycidyl-p-aminophenol and N, N-diglycidylaniline; hetero
  • polymerizable compounds (B) having an ethylenically unsaturated bond including the alkali developable compound (B ′) having the ethylenically unsaturated bond
  • the alkali developable compound (B ′) having the ethylenically unsaturated bond from the viewpoint of compatibility, alkali developability and heat resistance, Unsaturated aliphatic hydrocarbons, unsaturated polybasic acids, polyfunctional acrylates having an acid value, and (meth) acrylic esters are preferred, and unsaturated aliphatic hydrocarbons and unsaturated polybasic acids are more preferred.
  • the content of the polymerizable compound (B) having the ethylenically unsaturated bond is the content of the present invention.
  • the solid content of the coloring composition is preferably 30 to 99% by mass, particularly preferably 60 to 95% by mass. If the content of the polymerizable compound (B) having an ethylenically unsaturated bond is less than 30% by mass, the mechanical strength of the cured product is insufficient and cracks occur, or if it has alkali developability, development failure occurs. If it is larger than 99% by mass, curing due to exposure will be insufficient and tack will occur, or if it has alkali developability, the development time will be longer and the cured part will be filmed with alkali. There is a case.
  • Photopolymerization initiator (C) As the photopolymerization initiator (C), conventionally known compounds can be used. For example, benzophenone, phenylbiphenyl ketone, 1-hydroxy-1-benzoylcyclohexane, benzoin, benzyldimethyl ketal, 1-benzyl- 1-dimethylamino-1- (4′-morpholinobenzoyl) propane, 2-morpholyl-2- (4′-methylmercapto) benzoylpropane, thioxanthone, 1-chloro-4-propoxythioxanthone, isopropylthioxanthone, diethylthioxanthone, ethyl Anthraquinone, 4-benzoyl-4'-methyldiphenyl sulfide, benzoin butyl ether, 2-hydroxy-2-benzoylpropane, 2-hydroxy-2- (4'-isopropyl) benzoylpropane, 4-
  • N-1414, N-1717, N-1919, and PZ-4. 8 (manufactured by (Corporation) ADEKA Corporation) NCI-831, NCI-930, IRGACURE369, IRGACURE907, IRGACURE OXE 01, IRGACURE OXE 02 (BASF (Co.) Co., Ltd.).
  • photopolymerization initiators (C) from the viewpoint of sensitivity and color tone, 2-morpholylu 2- (4′-methylmercapto) benzoylpropane, 9-n-butyl-3,6-bis (2′-morpholinoisopetite). Royl) carbazole is preferred, and 2-morpholylu 2- (4′-methylmercapto) benzoylpropane is more preferred.
  • the content of the photopolymerization initiator (C) is preferably 0.1 to 30% by mass, particularly preferably 0.5 to 10% by mass in the colored composition of the present invention.
  • the content of the photopolymerization initiator (C) is less than 0.1% by mass, curing by exposure may be insufficient.
  • the initiator (C) is contained in the resin composition. May precipitate.
  • the coloring composition of the present invention may further contain a color material (D) other than the dye (A).
  • a color material (D) other than the dye (A) can be used alone or in admixture of two or more.
  • Examples of the colorant (D) include nitroso compounds, nitro compounds, azo compounds, diazo compounds, xanthene compounds, quinoline compounds, anthraquinone compounds, coumarin compounds, phthalocyanine compounds, isoindolinone compounds, isoindoline compounds, quinacridone compounds, Anthanthrone compounds, perinone compounds, perylene compounds, diketopyrrolopyrrole compounds, thioindigo compounds, dioxazine compounds, triphenylmethane compounds, quinophthalone compounds, naphthalene tetracarboxylic acids; lake pigments; carbon blacks obtained by furnace method, channel method, thermal method Or carbon black such as acetylene black, ketjen black or lamp black; the above carbon black adjusted and coated with epoxy resin
  • the carbon black previously dispersed with a resin in a solvent to adsorb 20 to 200 mg / g of resin, the carbon black treated with an acidic or alkaline surface, the average
  • pigments can also be used.
  • the content of the coloring material (D) is preferably 0 to 350 parts by mass, more preferably 100 parts by mass of the polymerizable compound (B) having an ethylenically unsaturated bond. Is 0 to 250 parts by mass. When it exceeds 350 parts by mass, the light transmittance of the colored composition of the present invention, particularly the cured product using the colored alkali-developable photosensitive composition, and the color filter for display device is lowered, and the luminance of the display device is lowered. Therefore, it is not preferable.
  • a solvent can be further added to the colored composition of the present invention.
  • the solvent is usually a solvent that can dissolve or disperse each of the above components (the dye (A) comprising the compound represented by the above general formula (I)) as necessary, for example, methyl ethyl ketone, methyl amyl ketone.
  • Ketones such as diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone; ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, dipropylene glycol dimethyl ether Ether solvents such as methyl acetate, ethyl acetate, acetic acid-n-propyl, isopropyl acetate, n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, texanol, etc .; ethylene glycol monomethyl ether, ethylene glycol Cellosolve solvents such as methanol monoethyl ether; alcohol solvents such as methanol, ethanol, iso- or n-propanol, iso- or n-
  • ketones, ether ester solvents, etc. particularly propylene glycol-1-monomethyl ether-2-acetate, cyclohexanone, and the like are preferable because the compatibility between the resist and the photopolymerization initiator is good in the colored composition.
  • the amount of the solvent used is such that the concentration of the composition other than the solvent is preferably 5 to 30% by mass, and if it is less than 5% by mass, it is difficult to increase the film thickness. Yes, it is not preferable because it cannot absorb light of a desired wavelength sufficiently, and when it is larger than 30% by mass, the storage stability of the composition due to the precipitation of the composition may be reduced, or the handling may be reduced because the viscosity is improved. There is.
  • the coloring composition of the present invention can further contain an inorganic compound.
  • the inorganic compound include metal oxides such as nickel oxide, iron oxide, iridium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, potassium oxide, silica, and alumina; lamellar clay mineral, miloli blue, calcium carbonate, Magnesium carbonate, cobalt, manganese, glass powder, mica, talc, kaolin, ferrocyanide, various metal sulfates, sulfides, selenides, aluminum silicate, calcium silicate, aluminum hydroxide, platinum, gold, silver, copper Among these, titanium oxide, silica, layered clay mineral, silver and the like are preferable.
  • the content of the inorganic compound is preferably 0.1 to 50 parts by mass, more preferably 0, relative to 100 parts by mass of the polymerizable compound (B) having the ethylenically unsaturated bond.
  • These inorganic compounds can be used alone or in combination of two or more.
  • inorganic compounds are used, for example, as fillers, antireflection agents, conductive agents, stabilizers, flame retardants, mechanical strength improvers, special wavelength absorbers, ink repellents, and the like.
  • a dispersant can be added.
  • any colorant or inorganic compound can be used as long as it can disperse and stabilize, and commercially available dispersants such as BYK series manufactured by BYK Chemie can be used, and polyester having a basic functional group, Polymer dispersant made of polyether, polyurethane, having a nitrogen atom as a basic functional group, the functional group having a nitrogen atom is an amine and / or a quaternary salt thereof, and an amine value of 1 to 100 mgKOH / g Those are preferably used.
  • the coloring composition of the present invention includes, if necessary, thermal polymerization inhibitors such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine; plasticizer; adhesion promoter; filler; Conventional additives such as an agent, a leveling agent, a surface conditioner, an antioxidant, an ultraviolet absorber, a dispersion aid, a coagulation inhibitor, a catalyst, an effect accelerator, a cross-linking agent, and a thickener can be added.
  • thermal polymerization inhibitors such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine
  • plasticizer such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine
  • adhesion promoter such as an agent, a leveling agent, a surface conditioner, an antioxidant, an ultraviolet absorber, a dispersion aid
  • the colored composition of the present invention optional components other than the dye (A), the polymerizable compound (B) having the ethylenically unsaturated bond, and the photopolymerization initiator (C) (however, the colorant (D) and
  • the content of the solvent (excluding the solvent) is appropriately selected according to the purpose of use and is not particularly limited, but is preferably a total with respect to 100 parts by mass of the polymerizable compound (B) having the ethylenically unsaturated bond. And 50 parts by mass or less.
  • the colored composition of the present invention improves the properties of the cured product comprising the colored composition of the present invention by using another organic polymer together with the polymerizable compound (B) having the ethylenically unsaturated bond.
  • the organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, poly (meth) acrylic acid, styrene- (meth) acrylic acid copolymer, (meth) acrylic acid-methyl methacrylate.
  • Copolymer ethylene-vinyl chloride copolymer, ethylene-vinyl copolymer, polyvinyl chloride resin, ABS resin, nylon 6, nylon 66, nylon 12, urethane resin, polycarbonate polyvinyl butyral, cellulose ester, polyacrylamide, saturated Polyester, phenolic resin, phenoxy resin, polyamideimide resin, polyamic acid resin, epoxy resin, and the like.
  • polystyrene, (meth) acrylic acid-methyl methacrylate copolymer, and epoxy resin are included.
  • the amount used is preferably 10 to 500 parts by mass with respect to 100 parts by mass of the polymerizable compound (B) having the ethylenically unsaturated bond.
  • a chain transfer agent a sensitizer, a surfactant, a silane coupling agent, a melamine compound and the like can be used in combination with the coloring composition of the present invention.
  • a sulfur atom-containing compound is generally used.
  • Alkyl compounds trimethylolpropane tris (3-mercaptoisobutyrate), butanediol bis (3-mercaptoisobutyrate), hexanedithiol, decanedithiol, 1,4- Methyl mercaptobenzene, butanediol bisthiopropionate, butanediol bisthioglycolate, ethylene glycol bisthioglycolate, trimethylolpropane tristhioglycolate, butanediol bisthiopropionate, trimethylolpropane tristhiopropionate , Trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakisthioglycolate, trishydroxyethyl tristhiopropionate, the following compound no. C1, aliphatic polyfunctional thiol
  • the surfactant examples include fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates, anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates, and higher amines. Cationic surfactants such as halogenates and quaternary ammonium salts, nonionic surfactants such as polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters and fatty acid monoglycerides, amphoteric surfactants, silicone surfactants Surfactants such as agents can be used, and these may be used in combination.
  • fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates
  • anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates,
  • silane coupling agent for example, a silane coupling agent manufactured by Shin-Etsu Chemical Co., Ltd. can be used. Among them, an isocyanate group, a methacryloyl group, or an epoxy group, such as KBE-9007, KBM-502, and KBE-403, can be used. A silane coupling agent is preferably used.
  • Examples of the melamine compound include all or part of active methylol groups (CH 2 OH groups) in nitrogen compounds such as (poly) methylol melamine, (poly) methylol glycoluril, (poly) methylol benzoguanamine, and (poly) methylol urea. Mention may be made of compounds in which (at least two) are alkyl etherified.
  • examples of the alkyl group constituting the alkyl ether include a methyl group, an ethyl group, and a butyl group, which may be the same as or different from each other.
  • the methylol group that is not alkyletherified may be self-condensed within one molecule, or may be condensed between two molecules to form an oligomer component.
  • hexamethoxymethyl melamine, hexabutoxymethyl melamine, tetramethoxymethyl glycoluril, tetrabutoxymethyl glycoluril and the like can be used.
  • alkyl etherified melamines such as hexamethoxymethyl melamine and hexabutoxymethyl melamine are preferable.
  • the coloring composition of the present invention is a known means such as spin coater, roll coater, bar coater, die coater, curtain coater, various printing, dipping, soda glass, quartz glass, semiconductor substrate, metal, paper, plastic, etc. It can be applied on the supporting substrate. Further, once applied on a supporting substrate such as a film, it can be transferred onto another supporting substrate, and the application method is not limited.
  • the active light source used for curing the colored composition of the present invention one that emits light having a wavelength of 300 to 450 nm can be used, for example, ultrahigh pressure mercury, mercury vapor arc, carbon arc. And xenon arc.
  • the laser direct drawing method that directly forms an image from digital information such as a computer without using a mask improves not only productivity but also resolution and positional accuracy.
  • the laser beam light having a wavelength of 340 to 430 nm is preferably used, but an argon ion laser, a helium neon laser, a YAG laser, a semiconductor laser, etc. are visible to infrared region. Those that emit light are also used. When these lasers are used, a sensitizing dye that absorbs light in the visible to infrared region is added.
  • the colored composition of the present invention is a liquid crystal display panel for color display such as a photocurable paint or varnish, a photocurable adhesive, a printed board or a color TV, a PC monitor, a portable information terminal, a digital camera, Color filters, color filters for CCD image sensors, electrode materials for plasma display panels, powder coatings, printing inks, printing plates, adhesives, dental compositions, resin for stereolithography, gel coats, photoresists for electronics, Electroplating resist, etching resist, both liquid and dry film, solder resist, forming a structure in the manufacturing process of plasma display panel, electroluminescent display device, and LCD for manufacturing color filters for various display applications
  • the colored alkali-developable photosensitive composition of the present invention is used for the purpose of forming a pixel of a color filter, and in particular, a photosensitizer for forming a color filter for a display device for an image display device such as a liquid crystal display panel or an organic EL. It is useful as a sex composition.
  • the color filter for display devices of the present invention may have red, green, blue, orange, purple and black optical elements in addition to the cured product of the present invention.
  • the color filter for display device includes (1) a step of forming a coating film of the colored composition of the present invention (particularly a colored alkali-developable photosensitive composition) on a substrate, and (2) a predetermined pattern shape on the coating film. Preferably formed by a step of irradiating actinic light through a mask having, (3) a step of developing a film after exposure with a developer (particularly an alkali developer), and (4) a step of heating the film after development. Is done.
  • the colored composition of the present invention is also useful as a colored composition for an ink jet system or a transfer system without a development step.
  • the production of a color filter for use in a liquid crystal display panel or the like is made by repeating the above steps (1) to (4) using a coloring composition of the present invention or other combinations and combining patterns of two or more colors. Can do.
  • the compound of the present invention is a novel compound represented by the above general formula (II).
  • the halogen atom represented by R 20 ′ a cyano group, a nitro group, or an alkyl group having 1 to 8 carbon atoms substituted with a hydroxyl group includes the above general formula ( Examples of the alkyl group having 1 to 8 carbon atoms substituted with a halogen atom, a cyano group, a nitro group or a hydroxyl group represented by R 1 to R 20 in I)
  • R 1 ′ , R 2 ′ , R 3 ′ , R 4 ′ , R 5 ′ , R 6 ′ , R 7 ′ , R 8 ′ , R 9 ′ and R 10 ′ and X ′ are CR 17 ′ R 18 ′ R 17 ′ and R 18 ′ when represented, R 19 ′ when X ′ is represented by NR 19 ′ , and C 1-8 represented by R 20 ′ when X is represented by PR 20 ′
  • Examples of the alkoxy group include those exemplified as the alkoxy group having 1 to 8 carbon atoms represented by R 1 to R 20 in the general formula (I).
  • R 1 ′ , R 2 ′ , R 3 ′ , R 4 ′ , R 5 ′ , R 6 ′ , R 7 ′ , R 8 ′ , R 9 ′ and R 10 ′ and X ′ are CR 17 ′ R 18 ′ when represented by R 17 'and R 18', X 'is NR 19' are replaced by halogen atoms represented by R 19 ', X' is 'R 20 when represented by' PR 20 when represented by Examples of the alkoxy group having 1 to 8 carbon atoms include those exemplified as the alkoxy group having 1 to 8 carbon atoms substituted by the halogen atom represented by R 1 to R 20 in the general formula (I). Is mentioned.
  • halogen atom represented by ' , R 14' , R 15 ' and R 16' include those exemplified as the halogen atoms represented by R 1 to R 16 in the general formula (I).
  • R 1 ′ and R 11 ′ , R 2 ′ and R 12 ′ , R 5 ′ and R 13 ′ , R 6 ′ and R 14 ′ , R 9 ′ and R 15 ′ and R 10 ′ and R 16 ′ are linked.
  • R 1 and R 11 , R 2 and R 12 , R 5 and R 13 , R 6 and R 14 , R 9 and R 15, and R 10 in the above general formula (I) What was illustrated as a 6-membered ring which R ⁇ 1 > can connect and form is mentioned.
  • the 6-membered ring that can be formed by linking R 4 ′ and R 5 ′ and R 6 ′ and R 7 ′ includes R 4 and R 5 and R 6 and R 7 in the general formula (I). What was illustrated as a 6-membered ring which can be formed is mentioned.
  • Examples of the 3- to 6-membered heterocyclic ring that can be formed by connecting R 11 ′ and R 12 ′ , R 13 ′ and R 14 ′ , and R 15 ′ and R 16 ′ include R 11 and R 12 , R 13 And R 14 , and R 15 and R 16 may be linked together to those exemplified as 3- to 6-membered heterocycles.
  • Examples of the anion represented by An q- include those exemplified in the above general formula (I).
  • R 4 ′ and R 7 ′ are preferably a substituent other than a hydrogen atom from the viewpoint of heat resistance, more preferably an electron-withdrawing group, and particularly preferably a halogen atom, especially a halogen atom.
  • R 11 ′ , R 12 ′ , R 13 ′ , R 14 ′ , R 15 ′ and R 16 ′ are substituted or unsubstituted alkyl having 1 to 8 carbon atoms from the viewpoint of solvent solubility. Groups are preferred.
  • X ′ is preferably an oxygen atom or a sulfur atom from the viewpoint of availability.
  • the compound No. 1 corresponds to the formula (II). 19-No. 24, Compound No. 25-No. 38, no. 41-No. 56, 58 to 62.
  • the compound represented by the general formula (II) is used as a dye in the above-described colored alkali-developable photosensitive composition, as well as an optical filter used for a display or an optical lens, a silver salt photographic photosensitive material, a dyed product. , Paints, optical recording dyes and the like.
  • Examples 1-1 to 1-4 show synthesis examples of the compounds of the present invention
  • Examples 2-1 to 2-5 are colored alkali-developable photosensitive composition Nos. 1-No.
  • Comparative Example 2-1 and 2-2 are comparative colored alkali-developable photosensitive composition Nos. 1-No. 2 shows a preparation example.
  • the colored alkali-developable photosensitive composition Nos. Obtained in Examples 2-1 to 2-5 were used.
  • 1-No. In Comparative Evaluation Examples 1-1 to 1-2, the comparatively colored alkali-developable photosensitive composition No. 5 obtained in Comparative Examples 2-1 to 2-2 was evaluated. 1-No. The heat resistance of 2 was evaluated.
  • Evaluation Example 2-1 the colored alkali-developable photosensitive composition No.
  • Example 2-2 1 obtained in Example 2-2 was used. 1 was evaluated.
  • Comparative Evaluation Example 2-2 the comparatively colored alkali-developable photosensitive composition No. 1 obtained in Comparative Example 2-2 was evaluated. As the solubility of 1, the solubility of the dye in the composition was evaluated.
  • Step 2 The leuco body obtained in Step 1, 0.05 mol, p-chloranil 0.75 mol, acetic acid 0.25 mol and hydrochloric acid 0.025 mol were mixed and stirred at 60 ° C. for 1 hour. The solid was filtered off, chloroform was added to the filtrate, and the aqueous layer was neutralized with an aqueous sodium bicarbonate solution. After adding 0.005 mol of potassium bis (trifluoromethanesulfonyl) imide and salt exchange, washing with water was performed to distill off the solvent from the organic layer.
  • the colored alkali-developable photosensitive composition using the compound of the present invention as a dye has little change in color difference, high heat resistance, and high solubility. Therefore, the compound of the present invention and the colored alkali-developable photosensitive composition of the present invention using this as a dye are useful for color filters for display devices.

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Abstract

La présente invention concerne une composition colorée photosensible contenant un colorant (A), comprenant : un composé représenté par la formule générale (I) ; un composé polymérisable (B) ayant une liaison éthyléniquement insaturée ; et un initiateur de photopolymérisation (C). Dans la formule générale (I), X représente idéalement un atome d'oxygène. De plus, au moins un type de matières colorantes (à l'exclusion du colorant (A)) contient idéalement (D). (Se rapporter à la description pour les définitions de R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16, et de X dans la formule. Dans la formule, q- représente un anion q-valent, q vaut 1 ou 2, et p représente un coefficient de maintien d'une charge neutre.)
PCT/JP2014/064411 2013-06-07 2014-05-30 Composition colorée photosensible et nouveau composé WO2014196464A1 (fr)

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US10875950B2 (en) 2015-08-13 2020-12-29 Fujifilm Corporation Coloring composition, cured film, color filter, method for manufacturing color filter, solid-state imaging device, image display device, and polymer
KR20210103852A (ko) 2020-02-14 2021-08-24 동우 화인켐 주식회사 착색 수지 조성물
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JP6824202B2 (ja) * 2017-03-27 2021-02-03 東友ファインケム株式会社Ｄｏｎｇｗｏｏ Ｆｉｎｅ−Ｃｈｅｍ Ｃｏ．， Ｌｔｄ． 着色樹脂組成物
CN108663902B (zh) * 2017-03-27 2023-05-09 东友精细化工有限公司 着色树脂组合物、滤色器和显示装置
WO2019093797A2 (fr) * 2017-11-10 2019-05-16 동우 화인켐 주식회사 Composition de résine durcissable colorante, filtre coloré, et dispositif d'affichage
TWI818883B (zh) * 2021-03-05 2023-10-11 日商旭化成股份有限公司 感光性樹脂積層體及其製造方法

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