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WO2018198920A1 - Composé et encre utilisant ledit composé - Google Patents

Composé et encre utilisant ledit composé Download PDF

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Publication number
WO2018198920A1
WO2018198920A1 PCT/JP2018/016077 JP2018016077W WO2018198920A1 WO 2018198920 A1 WO2018198920 A1 WO 2018198920A1 JP 2018016077 W JP2018016077 W JP 2018016077W WO 2018198920 A1 WO2018198920 A1 WO 2018198920A1
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WO
WIPO (PCT)
Prior art keywords
group
compound
general formula
meth
substituted
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Ceased
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PCT/JP2018/016077
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English (en)
Japanese (ja)
Inventor
木下　智之
文二 澤野
正之 江副
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Yamamoto Chemicals Inc
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Yamamoto Chemicals Inc
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Priority to JP2019514434A priority Critical patent/JP7128806B2/ja
Publication of WO2018198920A1 publication Critical patent/WO2018198920A1/fr
Anticipated expiration legal-status Critical
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    • 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
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine 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
    • C09B57/00—Other synthetic dyes of known constitution
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/02—Printing inks
    • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
    • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment

Definitions

  • the present invention relates to a novel compound, and in particular, a novel compound having a clear yellow hue, excellent light resistance, good solubility in organic solvents and resins, and dissolution stability, and a dye containing the same , Ink and coloring composition.
  • An ionic compound called a cationic dye or the like is composed of an organic cation having a positive charge delocalized over a conjugated bond, and usually an inorganic anion, and various paints, water-based inks, oil-based inks, inkjet inks, Used in a wide range of applications such as color filters.
  • Patent Document 1 discloses that an ionic styrylquinoline-based compound having a hexafluoroantimonate anion is used as a sensitizing dye in an image production method such as a photoresist.
  • Patent Document 2 discloses a wide range of dyes including styrylquinoline compounds having an anion selected from the group of cyanoboric acid, fluoroalkylphosphoric acid, fluoroalkylboric acid or imidized compounds.
  • Patent Document 3 discloses a diketopyridine compound which is a leuco dye used for pressure-sensitive and heat-sensitive recording materials. These compounds give a yellow color when contacted with silica gel or a phenol compound, but are not a colored substance used alone as a pigment like the compounds of the present application. These diketopyridine compounds have low solubility in organic solvents and resins.
  • Patent Document 4 discloses that a sulfonylimide-type counter anion having a photoreactive group is applied to a triarylmethane compound. The purpose is to improve the durability by introducing a polymerizable group, but the solubility in organic solvents and resins is insufficient, and the durability is not sufficiently improved.
  • An object of the present invention is to provide a novel compound that exhibits a clear yellowish hue, is excellent in light resistance, and has good solubility in organic solvents and resins.
  • the present invention (I) a compound represented by the following general formula (1), (In General Formula (1), A + represents the following General Formula (2) or General Formula (3), X represents an alkyl group in which at least a part of hydrogen atoms may be substituted with fluorine atoms, Y represents a divalent hydrocarbon group, and Z is a photoreactive group.)
  • R 1 to R 11 are each independently a hydrogen atom, a halogen atom, an alkyl group, a hydroxyl group, an alkoxy group, a nitro group, a dialkylamino group, an alkoxyalkyl group, or a substituted or unsubstituted aryl group.
  • R 12 to R 24 are each independently a hydrogen atom, a halogen atom, an alkyl group, a hydroxyl group, an alkoxy group, a nitro group, a dialkylamino group, an alkoxyalkyl group, or a substituted or unsubstituted aryl group.
  • Y in the general formula (1) is an arylene group
  • Z is a group selected from a vinyl group, an allyl group, a (meth) acryl group, and a (meth) acryloyl group
  • X is a perfluoroalkyl group.
  • the present invention it is possible to provide a compound that is excellent in durability, has good solubility in organic solvents and resins, and is suitable for dyes and inks.
  • FIG. 4 is an absorption spectrum diagram of the compound produced in Example 4 in methanol.
  • FIG. 6 is an absorption spectrum diagram of the compound produced in Example 5 in methanol.
  • FIG. 6 is an absorption spectrum diagram of the compound produced in Example 6 in methanol.
  • FIG. 6 is an absorption spectrum diagram of the compound produced in Example 7 in methanol.
  • FIG. 6 is an absorption spectrum diagram of the compound produced in Example 8 in methanol.
  • FIG. 6 is an absorption spectrum diagram of the compound produced in Example 9 in methanol.
  • FIG. 6 is an absorption spectrum diagram of the compound produced in Example 10 in methanol.
  • 2 is an absorption spectrum diagram of the compound produced in Example 11 in methanol.
  • FIG. FIG. 6 is an absorption spectrum diagram of the compound produced in Example 15 in methanol.
  • FIG. 4 is an absorption spectrum diagram of the compound produced in Example 16 in methanol.
  • 2 is an absorption spectrum diagram of the compound produced in Comparative Example 1 in methanol.
  • FIG. 4 is an absorption spectrum diagram of the compound produced in Comparative Example 2 in methanol.
  • a + represents the following General Formula (2) or General Formula (3)
  • X represents an alkyl group in which at least a part of hydrogen atoms may be substituted with fluorine atoms
  • Y represents a divalent hydrocarbon group
  • Z is a photoreactive group.
  • R 1 to R 11 are each independently a hydrogen atom, a halogen atom, an alkyl group, a hydroxyl group, an alkoxy group, a nitro group, a dialkylamino group, an alkoxyalkyl group, or a substituted or unsubstituted aryl group. Represents a group.
  • R 12 to R 24 are each independently a hydrogen atom, halogen atom, alkyl group, hydroxyl group, alkoxy group, nitro group, dialkylamino group, alkoxyalkyl group, or substituted or unsubstituted aryl. Represents a group.
  • X in the counter anion is preferably a fluorinated alkyl group having 1 to 3 carbon atoms in which part or all of the hydrogen atoms are substituted with fluorine atoms, and in particular, all hydrogen atoms
  • a perfluoroalkyl group in which is substituted with a fluorine atom is particularly preferred from the viewpoint of increasing the acidity of imidic acid and improving the stability of the dye.
  • trifluoromethyl group for example, trifluoromethyl group, difluoromethyl group, fluoromethyl group, pentafluoroethyl group, 2,2,2-trifluoroethyl group, 2-fluoroethyl group, 3,3,3-trifluoro A propyl group, a 3-fluoropropyl group, etc. can be mentioned.
  • the divalent hydrocarbon group represented by Y is not particularly limited, but for example, a straight chain or branched alkylene group having 1 to 10 carbon atoms, an arylene group having 6 to 20 carbon atoms, or a 7 to 20 carbon atoms.
  • An arylalkylene group etc. are mentioned.
  • the alkylene group includes a methylene group, an ethylene group, an n-propylene group, an isopropylene group, various butylene groups and the like
  • the arylene group includes a phenylene group and a naphthylene group.
  • Examples of the arylalkylene group include an arylmethylene group, an arylethylene group, and an arylpropylene group.
  • an arylalkylene group having 7 to 10 carbon atoms is preferable from the viewpoint of availability of raw materials and production, and an arylmethylene group, an arylethylene group, and an arylpropylene group are particularly preferable.
  • the arylalkylene group includes an ortho form, a meta form and a para form, but is preferably a para form from the viewpoint of no steric hindrance.
  • examples of the photoreactive group represented by Z include those in which the reaction proceeds through a polymerization reaction such as photo radical polymerization, photo cation polymerization, or photo anion polymerization.
  • examples of the radical photopolymerization reactive group include a functional group having an ethylenically unsaturated bond (preferably an ethylenic double bond).
  • a vinyl group, an allyl group, a (meth) acryl group, (Meth) acryloyl group, vinyl cycloalkyl group, etc. are mentioned.
  • a vinyl group, an allyl group, a (meth) acryl group, and a (meth) acryloyl group are preferable.
  • R 1 to R 11 are preferably a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a linear, branched or cyclic group having 1 to 20 carbon atoms.
  • alkoxy group, a nitro group, a linear, branched or cyclic dialkylamino group having 2 to 20 carbon atoms, a linear, branched or cyclic alkoxyalkyl group having 2 to 20 carbon atoms, or a substitution or substitution having 4 to 20 carbon atoms An unsubstituted aryl group.
  • the aryl group represents, for example, a carbocyclic aromatic group such as a phenyl group or a naphthyl group, or a heterocyclic aromatic group such as a furyl group, a thienyl group, or a pyridyl group.
  • the substituent of the aryl group includes a halogen atom, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, or a carbon number of 4 to
  • the aryl group which may be substituted by 20 said halogen atoms, an alkyl group, and an alkoxy group etc. are mentioned.
  • these substituents may be mono-substituted or poly-substituted.
  • R 1 to R 11 include, for example, a hydrogen atom; for example, a halogen atom such as a fluorine atom, a chlorine atom, or a bromine atom;
  • a hydrogen atom for example, a halogen atom such as a fluorine atom, a chlorine atom, or a bromine atom
  • phenyl group 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2-n-propylphenyl group, 3-n-propylphenyl group 4-n-propylphenyl group, 4-isopropylphenyl group, 3-n-butylphenyl group, 4-n-butylphenyl group, 4-isobutylphenyl group, 4-tert-butylphenyl group, 2-n-pentyl Phenyl group, 3-n-pentylphenyl group, 4-n-pentylphenyl group, 4-isopentylphenyl group, 4-tert-pentylphenyl group, 3-n-hexylphenyl group, 4-n-hexylphenyl group, 4-cyclohexylphenyl group, 3-n-heptylphenyl group, 4-n-heptylphen
  • 2-naphthyl group 4-methyl-1-naphthyl group, 4-ethoxy-1-naphthyl group, 6-n-butyl-2-naphthyl group, 6-methoxy-2-naphthyl group, 7-ethoxy-2-naphthyl group Group, 1-anthracenyl group, 2-anthracenyl group, 9-anthracenyl group, 2-tetracenyl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, 9,9-di-n-propyl-2- Fluorenyl group, 2-furyl group, 5-n-butyl-2-furyl group, 5-n-hexyl-2-furyl group, 5-n-octyl-2-furyl group, 2-thienyl group, 5-n- Propyl-2-thienyl group, 5-n-butyl-2-thienyl group, 5-n-hex
  • R 12 to R 24 may be the same as the substituents R 12 to R 24 in the general formula (2), and preferred ranges and specific examples thereof are also the same as those in the general formula.
  • Examples of the compound represented by the general formula (1) of the present invention are shown in the following exemplified compounds 1 to 16.
  • the compound represented by the general formula (1) will be described below by dividing it into a cation part and an anion part.
  • Examples of the cation moiety include structures represented by the following exemplified cation moieties 1 to 14.
  • anion moiety examples include the structures shown by the following exemplified anion moieties 1 to 3.
  • the compound represented by the general formula (1) of the present invention is produced by first producing the cation moiety from the corresponding raw material compound, and then ion-exchanging with the salt compound represented by the general formula (4). can do.
  • X represents an alkyl group in which at least a part of hydrogen atoms may be substituted with fluorine atoms
  • Y represents a divalent hydrocarbon group
  • Z represents a photoreactive group.
  • E represents a hydrogen atom, sodium, potassium, or trialkylamine.
  • the reaction solution can be used as it is as a cation moiety for the next step. Further, after the carboxylic acid ester salt is produced, the alcohol solution may be discharged into water and the precipitate may be isolated and used as a cation part.
  • Examples of the raw material compound include compounds represented by the following exemplified raw material compounds 1 to 14.
  • the step of performing ion exchange between the cation portion and the salt compound represented by the general formula (4) is performed by adding the salt compound represented by the general formula (4) to the cation portion generated in the step and stirring. .
  • the amount of the salt compound represented by the general formula (4) is about 1 to 3 equivalents with respect to the phthalide compound.
  • reaction solvent alcohol solvents such as methanol, ethanol and 2-propanol are preferable, halogen solvents such as chloroform, dichloromethane and dichloroethylene; aromatic solvents such as benzene, toluene and xylene; acetone, methyl ethyl ketone, methyl isobutyl ketone and the like Ketone solvents; ether solvents such as diethyl ether, dibutyl ether, 1,4-dioxane, and tetrahydrofuran; ester solvents such as ethyl acetate and butyl acetate may be used in combination.
  • You may add the salt compound represented by General formula (4) to the reaction liquid which manufactured the said cation part.
  • the reaction temperature is preferably 0 ° C to 40 ° C. After the reaction, it is discharged into water and the precipitate can be removed by filtration.
  • the compound represented by the general formula (1) of the present invention is suitable as a yellow dye in various applications such as water-based inks, oil-based inks, inkjet inks, color filter inks, various paints, and resin colorants.
  • a dye it is also preferable to use a dye having another structure in combination for the purpose of toning and the like.
  • the ink of the present invention contains the compound represented by the general formula (1) of the present invention, but simultaneously contains various solvents.
  • various solvents ethylene glycol monoalkyl ether acetates such as ethyl acetate, isopropyl acetate, cellosolve acetate, butyl cellosolve acetate; diethylene glycol monoalkyl ether acetates such as diethylene glycol monomethyl ether acetate, carbitol acetate, butyl carbitol acetate; propylene glycol Monoalkyl ether acetates; acetate esters such as dipropylene glycol monoalkyl ether acetates; ethylene glycol dialkyl ethers; diethylene glycol dialkyl ethers such as methyl carbitol, ethyl carbitol, and butyl carbitol; triethylene glycol dialkyl ethers Propylene glycol dialkyl ether Diether propylene glycol dialkyl ether
  • alkylene glycol monoalkyl ether acetates and acetate esters are preferred.
  • the ink of the present invention preferably further contains various resins. Various resins will be specifically described in the section of the colored composition described later.
  • the colored composition of the present invention contains at least the compound represented by the general formula (1) of the present invention and a resin.
  • a resin a thermoplastic resin, a thermosetting resin, a photosensitive resin, or the like is used.
  • the precursor of the resin include a monomer or an oligomer that is cured by ultraviolet irradiation to generate a resin. These can be used alone or in admixture of two or more.
  • the thermoplastic resin include acrylic resin, polystyrene resin, polyester resin, polyurethane resin, polyamide resin, polyimide resin, chlorinated polyethylene, chlorinated polypropylene, and polyvinyl chloride.
  • thermosetting resin examples include an epoxy resin, a melamine resin, a urea resin, and a phenol resin.
  • acrylic resin for example, two or more monomers selected from (meth) acrylic acid, (meth) acrylic acid ester monomers, (meth) acrylic acid hydroxyalkyl monomers, and the like are used, and preferably about 3 to 5 types are used. A resin polymerized to a molecular weight of about 5,000 to 100,000 can be used.
  • (meth) acrylic acid is used as a general term for acrylic acid and methacrylic acid.
  • Examples of the (meth) acrylic acid ester monomer include methyl (meth) acrylate, ethyl (meth) acrylate, (meth) acrylic acid-n-butyl, (meth) acrylic acid-tert-butyl, and (meth) acrylic. Acid-n-propyl and the like can be used.
  • Examples of the hydroxyalkyl monomer (meth) acrylate include (meth) acrylic acid, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate.
  • hydroxyalkyl (meth) acrylates Such as hydroxyalkyl (meth) acrylates, ⁇ -caprolactone condensate of the above hydroxyalkyl (meth) acrylates, polyethylene glycol mono (meth) acrylate, propylene glycol mono (meth) acrylate, (meth) acrylic acid There are -2-hydroxy-3-phenoxypropyl, pentaerythritol tri (meth) acrylate, and dipentaerythritol penta (meth) acrylate.
  • a monofunctional monomer a bifunctional monomer, a trifunctional monomer, or a polyfunctional monomer
  • a monofunctional monomer nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol, etc.
  • a bifunctional monomer tripropylene glycol diacrylate, Di (meth) acrylic acid tetraethylene glycol, di (meth) acrylic acid polyethylene glycol, etc. can be used.
  • Tri (meth) acrylic acid trimethylolpropane, tri (meth) acrylic acid pentaerythritol , Tris (2-hydroxyethyl) isocyanate and the like can be used.
  • Triazine compounds include 2- (p-methoxystyryl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4′-methoxy-1′-naphthyl) -4,6-bis (trichloro Methyl) -s-triazine, piperonyl-s-triazine and the like can be used.
  • imidazole compounds examples include 2,2′-bis- (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole, 2,2′-bis- (2- And chlorophenyl) -4,4 ′, 5,5′-tetra (3,4-methylenedioxyphenyl) -1,1′-bi-1H-imidazole.
  • benzophenone-based compound benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, and the like can be used.
  • These various photopolymerization initiators may be used alone or in combination.
  • the colored composition of the present invention may further contain various solvents. Further, various solvents may be contained in the process of producing the colored composition, and the solvent may be removed in the final form. Examples of the various solvents include the solvents shown in the above [Ink] section, but in addition, depending on the monomer composition of the acrylic resin used, the type of the photopolymerizable monomer, the type of the photopolymerization initiator, and the like. It can be selected as appropriate.
  • a solvent one or more kinds selected from toluene, xylene, ethyl cellosolve, ethyl cellosolve acetate, ethanol, ethyl acetate, propylene glycol monomethyl ether acetate, diglyme, cyclohexanone and the like are used.
  • Example raw material compound 1 was dissolved in 3.3 g of methanol and 50 mL of methanol, and 0.97 g of concentrated hydrochloric acid was added. 3.93 g of (p-vinylphenyl) trifluoromethanesulfonylimidic acid triethylamine salt prepared in Example 1 was added with stirring, and the mixture was further stirred at room temperature for 1 hour. The reaction solution was added to 200 mL of water, and the precipitate was collected by filtration and washed with water. Drying under reduced pressure gave 5.2 g of yellow powder. From the following analysis results, it was confirmed to be the target compound.
  • Example 4 The same procedure as in Example 4 was conducted, except that 2.6 g of exemplified raw material compound 2 was used instead of 3.3 g of exemplified raw material compound 1 used in Example 4, to obtain 5.1 g of yellow powder. From the following analysis results, it was confirmed to be the target compound.
  • the absorption spectrum of the methanol solution of the obtained compound was measured using an ultraviolet / visible spectrophotometer (Spectrophotometer U-4100 manufactured by Hitachi High-Technologies Corporation). ⁇ max was 385 nm.
  • the results of ultraviolet / visible spectroscopic analysis (UV-vis measurement) are shown in FIG.
  • Exemplified raw material compound 4 was dissolved in 2.8 g and 50 mL of methanol, and 0.97 g of concentrated hydrochloric acid was added. 5.38 g of (p-acryloyloxybutoxyphenyl) trifluoromethanesulfonylimidic acid triethylamine salt prepared in Example 3 was added, and the mixture was further stirred at room temperature for 1 hour. The reaction solution was added to 200 mL of water, and the precipitate was collected by filtration and washed with water. Drying under reduced pressure gave 5.2 g of yellow powder. From the following analysis results, it was confirmed to be the target compound.
  • Example 4 It processed like Example 4 except having used 5.1 g of exemplary raw material compound 10 instead of 3.3 g of exemplary raw material compound 1 used in Example 4, and obtained 7.2 g of yellow powder. From the following analysis results, it was confirmed to be the target compound.
  • the absorption spectrum of the methanol solution of the obtained compound was measured using an ultraviolet / visible spectrophotometer (Spectrophotometer U-4100 manufactured by Hitachi High-Technologies Corporation). ⁇ max was 371 nm.
  • Example 6 The same procedure as in Example 6 was conducted, except that 4.0 g of exemplified raw material compound 9 was used instead of 3.2 g of exemplified raw material compound 3 used in Example 6, to obtain 5.2 g of yellow powder. From the following analysis results, it was confirmed to be the target compound.
  • the absorption spectrum of the methanol solution of the obtained compound was measured using an ultraviolet / visible spectrophotometer (Spectrophotometer U-4100 manufactured by Hitachi High-Technologies Corporation). ⁇ max was 371 nm.
  • Example 7 It processed like Example 7 except having used 4.0 g of exemplary raw material compound 9 instead of 2.8 g of exemplary raw material compound 4 used in Example 7, and obtained 6.4 g of yellow powder. From the following analysis results, it was confirmed to be the target compound.
  • the absorption spectrum of the methanol solution of the obtained compound was measured using an ultraviolet / visible spectrophotometer (Spectrophotometer U-4100 manufactured by Hitachi High-Technologies Corporation). ⁇ max was 371 nm.
  • Example 4 The raw material compound 1 used in Example 4 was treated in the same manner as in Example 4 except that 4.5 g of Basic Blue 7 (CI-42595 Tokyo Chemical Industry Co., Ltd.) was used instead of 3.3 g. 6.7 g of a blue powder was obtained. From the following analysis results, it was confirmed that the compound was the target structural compound.
  • the absorption spectrum of the obtained compound in methanol solution was measured in the same manner as in Example 4, and ⁇ max was 594 nm.
  • the results of ultraviolet / visible spectroscopic analysis (UV-vis measurement) are shown in FIG.
  • Example 4 Instead of 3.3 g of Exemplified Raw Material Compound 1 used in Example 4, 4.6 g of Illustrative Raw Material Compound 7 and hexafluoro (p-vinylphenyl) trifluoromethanesulfonylimidic acid triethylamine salt instead of 3.93 g The same treatment as in Example 4 was carried out except that 2.7 g of sodium antimonate was used to obtain 5.3 g of yellow powder. From the following analysis results, it was confirmed to be the target compound.
  • dissolution refers to a state in which a solid cannot be seen by visual inspection. Further, the dissolution stability test was performed by the following method. The solution prepared by the above solubility test was allowed to stand at room temperature for 3 days, and the presence or absence of precipitation was visually confirmed.
  • Example 17 Production of Ink 1 7.0 g of Example Compound 1 prepared in Example 4, 6.3 g of polymethacrylic acid (weight average molecular weight 10,000) as an acrylic resin, and a combination of hydroxyethyl acrylate and methacrylic acid 6.3 g of polymer (weight average molecular weight 30,000), 3 g of 2-hydroxy-3-phenoxypropyl acrylate, 2- (p-methoxystyryl) -4,6-bis (trichloromethyl) -s-triazine was mixed with 0.8 g and 77 g of PGMEA (propylene glycol monomethyl ether acetate), and stirred with a rotary stirrer (rotation speed: 1,000 rpm, time: 10 minutes) to produce an ink.
  • PGMEA propylene glycol monomethyl ether acetate
  • Examples 18 to 29 Production of inks 2 to 13 Ink 2 was prepared in the same manner as in Example 17 except that the compounds produced in Examples 5 to 16 were used instead of the exemplified compound 1 in Example 17. ⁇ 13 were produced.
  • Comparative Examples 3 and 4 Preparation of Comparative Inks 1 and 2 Comparative Inks were carried out in the same manner as in Example 17 except that the compounds prepared in Comparative Examples 1 and 2 were used instead of Exemplified Compound 1 in Example 17. 1 and 2 were produced.
  • Examples 30 to 42 Production of coloring compositions 1 to 13 On a glass substrate, the inks 1 to 13 produced in Examples 17 to 29 were spin-coated (3000 rpm, 10 sec), dried, and dried at 70 ° C. for 20 minutes. Pre-baked and exposed (50 mJ / cm 2 ). After thoroughly washing with water, it was dried and baked at 230 ° C. for 1 hour to produce colored compositions 1 to 13.
  • Comparative Examples 5 and 6 Production of Comparative Colored Compositions 1 and 2 On a glass substrate, the comparative inks 1 and 2 produced in Comparative Examples 3 and 4 were spin-coated (3000 rpm, 10 sec), dried, and dried at 70 ° C. Pre-baked for 20 minutes and exposed (50 mJ / cm 2 ). After sufficiently washing with water, it was dried and baked at 230 ° C. for 1 hour to produce comparative colored compositions 1 and 2.
  • the compound of the present invention was excellent in solubility and dissolution stability in solvents and resins, and the colored composition containing the compound was excellent in light resistance.
  • the compound of the present invention has excellent light resistance, good solubility in organic solvents and resins and good dissolution stability, and is suitable for uses such as dyes, inks, and resin colorants.

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  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Inorganic Chemistry (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

L'invention concerne un nouveau composé qui présente une excellente solidité à la lumière, une bonne stabilité de dissolution et une bonne solubilité dans des solvants organiques et des résines, et qui convient à une utilisation dans des colorants, des encres jaunes et analogues. Le composé est représenté par la formule générale (1). (Dans la formule générale (1), A+ représente une structure telle celle qui est présentée dans la formule générale (2), X est un groupe alkyle dans lequel au moins quelques-uns des atomes d'hydrogène peuvent être substitués par des atomes de fluor, Y est un groupe hydrocarboné divalent, et Z est un groupe photoréactif.) (Dans la formule générale (2), R1 à R11 représentent chacun d'une manière indépendante un atome d'hydrogène, un atome d'halogène, un groupe alkyle, un groupe hydroxyle, un groupe alcoxy, un groupe nitro, un groupe dialkylamino, un groupe alcoxyalkyle ou un groupe aryle substitué ou non substitué.)
PCT/JP2018/016077 2017-04-28 2018-04-19 Composé et encre utilisant ledit composé Ceased WO2018198920A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5883673A (ja) * 1981-11-10 1983-05-19 Yamamoto Kagaku Gosei Kk 発色性ジケトピリジン化合物
JPH09512351A (ja) * 1994-04-25 1997-12-09 ポラロイド コーポレイション 画像媒体およびそのプロセス
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JP2012072205A (ja) * 2010-09-27 2012-04-12 Dainippon Printing Co Ltd トリアリールメタン系染料
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JPS5883673A (ja) * 1981-11-10 1983-05-19 Yamamoto Kagaku Gosei Kk 発色性ジケトピリジン化合物
JPH09512351A (ja) * 1994-04-25 1997-12-09 ポラロイド コーポレイション 画像媒体およびそのプロセス
JP2004292507A (ja) * 2003-03-25 2004-10-21 Toppan Printing Co Ltd 着色組成物及び感光性着色組成物及びカラーフィルタ
JP2007503477A (ja) * 2003-08-21 2007-02-22 メルク　パテント　ゲゼルシャフト　ミット　ベシュレンクテル　ハフトング シアノホウ酸塩、フルオロアルキルリン酸塩、フルオロアルキルホウ酸塩またはイミド染料
JP2012072205A (ja) * 2010-09-27 2012-04-12 Dainippon Printing Co Ltd トリアリールメタン系染料
JP2013163804A (ja) * 2012-01-12 2013-08-22 Jsr Corp 着色剤、着色組成物、カラーフィルタ及び表示素子

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