WO2017029903A1 - フタロシアニン化合物およびその製造方法、ならびに該フタロシアニン化合物を含有するカラーフィルタ、着色組成物 - Google Patents
フタロシアニン化合物およびその製造方法、ならびに該フタロシアニン化合物を含有するカラーフィルタ、着色組成物 Download PDFInfo
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- WO2017029903A1 WO2017029903A1 PCT/JP2016/070106 JP2016070106W WO2017029903A1 WO 2017029903 A1 WO2017029903 A1 WO 2017029903A1 JP 2016070106 W JP2016070106 W JP 2016070106W WO 2017029903 A1 WO2017029903 A1 WO 2017029903A1
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- compound
- phthalocyanine compound
- general formula
- phthalocyanine
- color filter
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- 0 *N(c(cc(c(C#N)c1)C#N)c1N1*)C1=O Chemical compound *N(c(cc(c(C#N)c1)C#N)c1N1*)C1=O 0.000 description 2
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains four or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/26—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
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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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/06—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide
- C09B47/067—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile
- C09B47/0676—Preparation from carboxylic acids or derivatives thereof, e.g. anhydrides, amides, mononitriles, phthalimide, o-cyanobenzamide from phthalodinitriles naphthalenedinitriles, aromatic dinitriles prepared in situ, hydrogenated phthalodinitrile having nitrogen atom(s) linked directly to the skeleton
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- 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
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
Definitions
- the present invention relates to a phthalocyanine compound that can be used as a green pigment, a method for producing the same, a color filter containing the phthalocyanine compound, and a coloring composition.
- a typical example of a conventionally known green pigment is polyhalogenated copper phthalocyanine.
- This polyhalogenated copper phthalocyanine has excellent fastness, but since it has a large amount of halogen atoms such as chlorine and bromine in the molecule, there are concerns about its safety and environmental burden in recent years.
- polyhalogenated phthalocyanine since polyhalogenated phthalocyanine has a large amount of halogen atoms, there is a problem that the molecular weight is increased and the coloring power is lowered. Therefore, a pigment that can be colored green with a compound having no halogen atom is required.
- a halogen-free compound having a single green hue for example, a phthalocyanine compound into which an imidazolone ring is introduced is reported in Patent Document 3, and a phthalocyanine compound into which a pyrido skeleton is introduced is reported in Patent Document 4. Since the phthalocyanine compound described in Patent Document 3 exhibits a green hue, there is no need for toning, and it has characteristics of having an organic solvent and acid resistance. However, there was a problem of low saturation.
- Patent Document 5 reports a phthalocyanine compound into which a disubstituted imidazolone structure or a piperazinedione structure in which alkyl groups are symmetrically substituted with N, N'- is introduced.
- a phthalocyanine compound into which a disubstituted imidazolone structure or a piperazinedione structure in which alkyl groups are symmetrically substituted with N, N'- is introduced.
- it is difficult to disperse into liquid (liquid medium) and paste (solid), and it has not been possible to achieve the required characteristics with higher high saturation.
- An object of the present invention is to provide a phthalocyanine compound which has a halogen-free green hue and has high luminance and excellent coloring power when used for adjusting a green pixel portion of a color filter.
- one or more phthalocyanine compounds selected from the compounds represented by the following general formula (1) and general formula (2) are halogen-free. It has been found that when it is used to adjust the green pixel portion of the color filter, it has a green hue and has high luminance and excellent coloring power.
- the present invention relates to a phthalocyanine compound represented by one or more phthalocyanine compounds selected from compounds represented by general formula (1) and general formula (2).
- R 1 to R 8 each independently represents an alkyl group having 1 to 6 carbon atoms or an aralkyl group having 7 to 9 carbon atoms, provided that R 1 And R 2 , R 3 and R 4 , R 5 and R 6 , R 7 and R 8 each represent a different group.
- M represents a divalent to tetravalent metal atom (wherein the metal atom may be oxidized).
- the divalent to tetravalent metal atom represented by M is copper or zinc.
- R 1 to R 8 are each independently an alkyl group having 1 to 4 carbon atoms, provided that R 1 and R 2 , R 3 and R 4 , R 5 and R 6 , R 7 and R 8 are phthalocyanine compounds as described above, each representing a different group.
- R 9 and R 10 each independently represents an alkyl group having 1 to 6 carbon atoms or an aralkyl group having 7 to 9 carbon atoms, provided that R 9 and R 10 are different groups. To express.
- R 9 and R 10 each independently represents an alkyl group having 1 to 6 carbon atoms or an aralkyl group having 7 to 9 carbon atoms, provided that R 9 and R 10 are different groups.
- X represents O or NH.
- One or more compounds selected from the compounds represented by the general formula (3) and the general formula (4) alone or a divalent to tetravalent metal atom represented by M in the general formula (1) The method for producing a phthalocyanine compound according to the above, wherein the mixture with a metal salt corresponding to is thermally condensed.
- a coloring composition comprising the phthalocyanine compound described above is provided. Provide.
- the phthalocyanine compound of the present invention has a green hue, and provides a phthalocyanine compound having high luminance and excellent coloring power when used for adjusting a green pixel portion of a color filter.
- the phthalocyanine compound of the present invention is halogen-free, it is characterized by high safety and low environmental load. Therefore, it is very useful as a substitute for a halogenated phthalocyanine pigment, which is an existing green pigment, for applications requiring environmental measures.
- the phthalocyanine compound of the present invention Since the phthalocyanine compound of the present invention has the above characteristics, it is used as a colorant for a wide range of uses as a general colorant for printing inks, paints, colored plastics, toners, and ink-jet inks in addition to color filter applications. be able to.
- each of the four benzene skeletons of the phthalocyanine has N, N alkyl groups and aralkyl groups in the imidazolone structure that are not identical to each other.
- '-A compound in which a disubstituted imidazolone structure is introduced is introduced.
- a compound in which a metal is complexed at the central portion of phthalocyanine is represented by the general formula (1), and a metal-free compound is represented by the general formula (2). Both are green.
- the phthalocyanine compound represented by general formula (1) is referred to as compound (1)
- the phthalocyanine compound represented by general formula (2) is referred to as compound (2).
- Synthesis examples of the compound (1) or the compound (2) of the present invention are described below.
- a dicyano compound represented by the following general formula (3) which is a dinitrile compound having an N, N′-disubstituted imidazolone ring as an intermediate thereof, is used.
- a benzimidazolone compound or a phthalic anhydride and a phthalimide compound represented by the following general formula (4) are synthesized by the following synthesis method.
- R 9 and R 10 each independently represents an alkyl group having 1 to 6 carbon atoms or an aralkyl group having 7 to 9 carbon atoms, provided that R 9 and R 10 are different groups. To express.
- R 9 and R 10 each independently represents an alkyl group having 1 to 6 carbon atoms or an aralkyl group having 7 to 9 carbon atoms, provided that R 9 and R 10 are different groups.
- X represents O or NH.
- the general formula (3) can be synthesized, for example, by the following method.
- Compound (6) is obtained by substituting the nitro group of compound (5) obtained by dinitrating o-dibromobenzene at positions 4 and 5 with an amine. The bromine atom is then replaced with a cyano group, and the nitro group is reduced.
- the obtained diamino compound (8) is reacted with phosgene, chlorocarbonate, urea or 1,1′-carbonylbis-1H-imidazole in an organic solvent such as acetonitrile at 0 to 130 ° C. for about 1 to 6 hours.
- a dicyanobenzimidazolone compound represented by the following formula (9) (hereinafter referred to as “compound (9)”) can be obtained.
- the compound (9) is dissolved in an organic solvent such as N, N-dimethylformamide, N-methyl-2-pyrrolidinone, dimethyl sulfoxide in the presence of a base such as sodium hydride, cesium carbonate, potassium carbonate, potassium t-butoxide,
- An N, N′-disubstituted dicyanobenzimidazolone compound represented by the general formula (3) (hereinafter referred to as “compound (3)” by reacting with one of the compounds such as alkyl halide and halogenated aralkyl. ) ").)
- compound (3) by reacting with one of the compounds such as alkyl halide and halogenated aralkyl.
- Y represents a sulfonate group such as a chlorine atom, a bromine atom, an iodine atom, or a tosyl group, a mesyl group, or a trifluoromethanesulfonyl group.
- Compound (7) can also be synthesized by substituting the bromine atom of 4-bromo-5-nitrophthalonitrile (10) with an amine. Details of this method are described in Mendeleev Communications, 78 (2000).
- the general formula (4) can be synthesized, for example, by the following method.
- the dicarboxylic acid (11) is obtained by hydrolyzing the compound (3).
- the compound (11) is reacted with acetic anhydride or the like to dehydrate, thereby obtaining an acid anhydride represented by X ⁇ O in the general formula (4).
- the compound represented by X ⁇ O in the general formula (4) is reacted with ammonia or formamide to obtain the compound represented by X ⁇ NH in the general formula (4).
- the compound (1) of the present invention includes a compound (3) or compound (4) obtained by the above synthesis method, and a metal salt corresponding to a divalent to tetravalent metal atom represented by M in the general formula (1) Can be obtained by heat condensation at 120 to 250 ° C. in an organic solvent.
- the compound (2) of the present invention can be obtained by synthesis without using a metal salt corresponding to the divalent to tetravalent metal atom in the synthesis method.
- Examples of the divalent to tetravalent metal atom represented by M in the general formula (1) include magnesium, aluminum, titanium, vanadium, iron, cobalt, nickel, copper, zinc, platinum, palladium and the like. Of these, titanium, vanadium, iron, cobalt, nickel, copper, and zinc are preferable, and vanadium, cobalt, copper, and zinc are most preferable. These metals may be oxidized.
- metal salt corresponding to the divalent to tetravalent metal atom various salts such as halogen salts, acetates, sulfates, nitrates, carbonates and the like can be used, preferably halogen salts and acetates.
- Examples of the organic solvent used in the synthesis of the compound (1) or the compound (2) include alcohols, glycols, trichlorobenzene, quinoline, ⁇ -chloronaphthalene, nitrobenzene, sulfolane, N, N-dimethylformamide and the like. Is mentioned. Moreover, you may react without a solvent.
- DBU 1,8-diazabicyclo [5,4,0] undec-7-ene
- DBN diazabicyclo [4,3,0] non-5-ene
- cyclohexylamine is preferred because the yield is improved.
- Examples of the alkyl group having 1 to 6 carbon atoms represented by R 1 to R 8 in the compound (1) and the compound (2) include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a pentyl group, A hexyl group etc. are mentioned.
- Examples of the aralkyl group having 7 to 9 carbon atoms include benzyl group, 2-phenylethyl group, and 3-phenylpropyl group.
- R 1 to R 8 in the general formulas (1) and (2) are preferably a methyl group, an ethyl group, a propyl group, and a butyl group, and particularly preferably a methyl group, an ethyl group, and a propyl group.
- R 1 and R 2 , R 3 and R 4 , R 5 and R 6 , and R 7 and R 8 represent different groups. It is considered that by making the substituents asymmetry, the cohesiveness of the pigment particles is reduced as compared with the case where R 1 to R 8 are all the same, the dispersibility is improved, and the dispersion viscosity is greatly reduced.
- the compound (1) or compound (2) is obtained as a green crude pigment by the above synthesis method, it is preferably subjected to a pigmentation treatment when used as a colorant.
- a pigmentation treatment examples include solvent salt milling, salt milling, dry milling, solvent milling, grinding treatment such as acid pasting, solvent heating treatment, and the like.
- the phthalocyanine compound of the present invention When used as a green pigment, it is preferable to carry out the pigmentation treatment as described above and adjust the pigment particle diameter to a range of 0.01 to 1.5 ⁇ m. Solvent salt milling in which the average length / width ratio of particles (so-called average aspect ratio) is less than 3 and closer to 1 and a narrower particle size distribution is obtained in the electron micrograph of the obtained pigment is a preferred pigment. Process.
- green pigment when used as a green pigment as described above, it may be simply mixed with many organic pigments and inorganic pigments, or may be pulverized and mixed. Further, it may of course be in the form of a mixture or a solid solution with a primary particle size such as acid pasting.
- pigment derivatives, surfactants and additives used for general dispersibility, particle growth control inhibition, heat resistance, weather resistance, and light resistance can be used in combination.
- the phthalocyanine compound of the present invention is used for the production of a color filter pixel part because it has a small hue change and excellent heat resistance even after a thermal history at high temperatures in various known and commonly used applications.
- a color filter for a liquid crystal display device capable of displaying an excellent image with little hue change can be obtained.
- a photosensitive composition for a color filter pixel portion for example, the organic pigment composition of the present invention, a photosensitive resin, a photopolymerization initiator, and an organic solvent that dissolves the resin are mixed as essential components.
- a method of preparing a dispersion by using the organic pigment composition of the present invention, an organic solvent, and a dispersant as required, and then adding a photosensitive resin or the like to the dispersion is generally used. is there.
- the conventional cold cathode tube CCFL light source
- white LED LED; Light Emitting Diode
- three-color independent LED light source white organic EL (EL; Electro Luminescence)
- EL Electro Luminescence
- the phthalocyanine compound of the present invention includes a sulfonic acid derivative of metal-free or metal phthalocyanine, an N- (dialkylamino) methyl derivative of metal-free or metal phthalocyanine, an N- (dialkylaminoalkyl) sulfonic acid amide of metal-free or metal phthalocyanine.
- the phthalocyanine compound of the present invention itself has a hue suitable for the preparation of a color filter green pixel portion. If necessary, per 100 parts by mass of copper halide phthalocyanine (CI pigment green). 7, 36), and zinc halide phthalocyanine (CI Pigment Green 58) may be used in an amount of 0.1 to 50 parts.
- C.I. which is a yellow pigment. I. Pigment yellow 129, C.I. I. Pigment yellow 138, C.I. I.
- Various yellow pigments such as CI Pigment Yellow 139 can be added to adjust the hue and transmission wavelength.
- the phthalocyanine compound of the present invention itself has light resistance suitable for the preparation of a color filter green pixel part, but if necessary, 0.1 to 10 parts of non-volatile antioxidant per 100 parts of the phthalocyanine compound. In particular, 0.5 to 8 parts can be used.
- antioxidant is a general term for additives that prevent oxidative degradation. Those that prevent oxidative degradation due to heat (antioxidants in a narrow sense) and those that prevent oxidative degradation due to light (mainly ultraviolet rays). (Referred to in the narrow sense as light stabilizers). *
- antioxidants have the ability to trap radicals and prevent auto-oxidation (radical chain prevention) and the action to decompose hydroperoxide (peroxide) into harmless ones (peroxide decomposition action)
- the former is called a primary antioxidant and the latter is called a secondary antioxidant.
- primary antioxidants include phenolic (including hindered phenols) and amine (including hindered amines) antioxidants
- secondary antioxidants include, for example, sulfur and phosphorus. Each of these antioxidants is typical.
- the phthalocyanine compound of the present invention can be further combined with a cationic resin to further improve heat resistance and light resistance.
- a cationic resin for example, an acrylic resin, a polyurethane resin, an epoxy resin, a polyamide resin, or the like is preferably used because the hue change is small even under a thermal history and the heat resistance of the color filter can be greatly improved.
- the ratio of the phthalocyanine compound and the cationic resin on the basis of mass of the non-volatile content is not particularly limited, but the non-volatile content of the latter resin is 0.1 part or more and less than 10 parts per 100 parts of the former compound.
- the amount is preferably 0.5 to 5 parts, particularly 1 to 3 parts.
- the coloring composition containing the phthalocyanine compound and the cationic resin when the compound and the resin are heated, after mixing the two, a temperature at which no trouble occurs in the compound itself in a closed system
- the reaction can be carried out in the range of 30 minutes to 5 hours with stirring.
- a typical method for producing a color filter using the phthalocyanine compound of the present invention is a photolithography method, which includes a photocurable composition described later on a side provided with a black matrix of a transparent substrate for a color filter. After applying to the surface, heating and drying (pre-baking), pattern exposure is performed by irradiating ultraviolet rays through a photomask to cure the photo-curable compound at the location corresponding to the pixel portion, and then the unexposed portion Is developed with a developing solution, the non-pixel portion is removed, and the pixel portion is fixed to the transparent substrate.
- a pixel portion made of a cured colored film of a photocurable composition is formed on a transparent substrate.
- a photocurable composition to be described later is prepared, and the above-described operation is repeated to manufacture a color filter having red, green, and blue colored pixel portions at predetermined positions. be able to.
- a green pixel portion can be formed from the phthalocyanine compound of the present invention.
- a well-known and usual red pigment and blue pigment can be used.
- C.I. I. Pigment Red 177, 209, 242 and 254 are pigments for forming a blue pixel portion, such as C.I. I. Pigment blue 1, 15: 6, 60, 80, and the like.
- a yellow pigment can be used in combination.
- a purple pigment can also be used in combination for forming the blue pixel portion.
- the entire color filter can be heat-treated (post-baked) in order to thermally cure the unreacted photocurable compound.
- Examples of a method for applying a photocurable composition described later on a transparent substrate such as glass include a spin coating method, a roll coating method, and an ink jet method.
- the drying conditions of the coating film of the photocurable composition applied to the transparent substrate vary depending on the type of each component, the blending ratio, and the like, but are usually about 50 to 150 ° C. for about 1 to 15 minutes.
- light used for photocuring the photocurable composition it is preferable to use light in the wavelength region of 200 to 500 nm. Various light sources that emit light in this wavelength range can be used.
- Examples of the developing method include a liquid filling method, a dipping method, and a spray method.
- the transparent substrate on which the necessary color pixel portion is formed is washed with water and dried.
- the color filter thus obtained is subjected to a heat treatment (post-baking) at 90 to 280 ° C. for a predetermined time by a heating device such as a hot plate or an oven, thereby removing volatile components in the colored coating film and simultaneously applying light.
- the unreacted photocurable compound remaining in the cured colored film of the curable composition is thermally cured to complete the color filter.
- the photocurable composition for forming the green pixel portion of the color filter includes the phthalocyanine compound of the present invention, a dispersant, a photocurable compound, and an organic solvent as essential components, and if necessary, a thermoplastic resin. Can be prepared by mixing them.
- a photocurable compound is used in preparing the photocurable composition.
- a thermoplastic resin is used in combination, it is preferable to use an organic solvent that dissolves it.
- the phthalocyanine compound of the present invention As a method for producing the photocurable composition, the phthalocyanine compound of the present invention, an organic solvent and a dispersant are used as essential components, and these are mixed and stirred and dispersed so as to be uniform. After preparing a dispersion for forming the pixel portion, a photocurable compound and, if necessary, a thermoplastic resin, a photopolymerization initiator, etc. are added to obtain the photocurable composition. Is common.
- organic solvent examples include aromatic solvents such as toluene, xylene and methoxybenzene, acetate solvents such as ethyl acetate and butyl acetate, propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether acetate, and ethoxyethyl propionate.
- Propionate solvents such as methanol, ethanol solvents such as ethanol, butyl cellosolve, ether solvents such as propylene glycol monomethyl ether, diethylene glycol ethyl ether, diethylene glycol dimethyl ether, ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, hexane, etc.
- Aliphatic hydrocarbon solvents N, N-dimethylformamide, ⁇ -butyrolactam, N-methyl-2-pyrrolidone Aniline, nitrogen compound-based solvent such as pyridine, a lactone-based solvents such as ⁇ - butyrolactone, carbamic acid esters such as a mixture of 48:52 of methyl carbamate and ethyl carbamate, there is water.
- nitrogen compound-based solvent such as pyridine
- a lactone-based solvents such as ⁇ - butyrolactone
- carbamic acid esters such as a mixture of 48:52 of methyl carbamate and ethyl carbamate
- organic solvent polar solvents such as propionate-based, alcohol-based, ether-based, ketone-based, nitrogen compound-based, lactone-based, water and the like that are water-soluble are particularly suitable.
- thermoplastic resin used for the preparation of the photocurable composition examples include urethane resins, acrylic resins, polyamide resins, polyimide resins, styrene maleic acid resins, styrene maleic anhydride resins, and the like. .
- photocurable compound examples include 1,6-hexanediol diacrylate, ethylene glycol diacrylate, neopentyl glycol diacrylate, triethylene glycol diacrylate, bis (acryloxyethoxy) bisphenol A, and 3-methylpentanediol diacrylate.
- Relatively molecular weights such as bifunctional monomers such as acrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, tris [2- (meth) acryloyloxyethyl) isocyanurate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate Small polyfunctional monomer, polyester acrylate, polyurethane acrylate, polyether acrylate, etc. Functional monomer.
- photopolymerization initiator examples include acetophenone, benzophenone, benzyldimethyl ketal, benzoyl peroxide, 2-chlorothioxanthone, 1,3-bis (4′-azidobenzal) -2-propane, 1,3-bis (4′- Azidobenzal) -2-propane-2′-sulfonic acid, 4,4′-diazidostilbene-2,2′-disulfonic acid, and the like.
- photopolymerization initiators examples include “Irgacure (trade name) -184”, “Irgacure (trade name) -369”, “Darocur (trade name) -1173” manufactured by Ciba Specialty Chemicals, and BASF Corporation. “Lucirin-TPO”, Nippon Kayaku Co., Ltd. “Kayacure (trade name) DETX”, “Kayacure (tradename) OA”, Stoffer “Bicure 10”, “Bicure 55”, Akzo Corporation “Trigonal PI” “Sandray 1000” manufactured by Sand, “Deep” manufactured by Upjohn, and “Biimidazole” manufactured by Kurokin Kasei.
- a known and commonly used photosensitizer can be used in combination with the photopolymerization initiator.
- the photosensitizer include amines, ureas, compounds having a sulfur atom, compounds having a phosphorus atom, compounds having a chlorine atom, nitriles or other compounds having a nitrogen atom. These can be used alone or in combination of two or more.
- the blending ratio of the photopolymerization initiator is not particularly limited, but is preferably in the range of 0.1 to 30% with respect to the compound having a photopolymerizable or photocurable functional group on a mass basis. If it is less than 0.1%, the photosensitivity at the time of photocuring tends to decrease, and if it exceeds 30%, when the resist coating film is dried, crystals of the photopolymerization initiator are precipitated, and the coating film properties. May cause deterioration.
- the developer a known and commonly used organic solvent or alkaline aqueous solution can be used.
- the photocurable composition contains a thermoplastic resin or a photocurable compound, and at least one of them has an acid value and exhibits alkali solubility
- the color filter can be washed with an alkaline aqueous solution. It is effective for forming the pixel portion.
- the method for producing a color filter pixel portion by photolithography was described in detail.
- the color filter pixel portion prepared using the phthalocyanine compound of the present invention is not limited to other electrodeposition methods.
- a color filter may be manufactured by forming a green pixel portion by a transfer method, a micelle electrolysis method, a PVED (Photovoltaic Electrodeposition) method, an ink jet method, a reverse printing method, a thermosetting method, or the like.
- the color filter uses a photocurable composition of each color obtained by using a red pigment, a blue pigment, and the phthalocyanine compound of the present invention as an organic pigment, and encloses a liquid crystal material between a pair of parallel transparent electrodes,
- the transparent electrode is divided into discontinuous fine sections, and each of the fine sections divided into a grid by the black matrix on the transparent electrode is colored with a color filter selected from one of red, green, and blue It can be obtained by providing the pixel portions alternately in a pattern or by providing a transparent electrode after forming the color filter colored pixel portions on the substrate.
- the phthalocyanine compound of the present invention can provide a dispersion having excellent clarity and lightness, and for color filter applications, paints, plastics (resin molded products), printing inks, rubber, leather, textile printing, electrostatic image development.
- the present invention can also be applied to coloring toner, ink jet recording ink, thermal transfer ink, and the like.
- the colored composition of the present invention is a composition containing the phthalocyanine compound of the present invention as a colorant together with a synthetic resin, and includes, for example, printing inks, paints, colored plastics, toners, inkjet inks, color filter color pastes, and the like. Examples include color resists.
- the application is not particularly limited as long as the phthalocyanine compound of the present invention can be colored.
- Synthetic resins used for the preparation of the colored composition of the present invention include, for example, polymerization resins and condensation resins, particularly urea resins / formaldehyde resins and melamine / formaldehyde resins, alkyd resins, phenol resins, polyester resins, polyamide resins, and polyvinyl chloride. , Polyurethane, acrylic / melamine, polystyrene, cellulose ether, nitrocellulose, polyacrylate, polyacrylonitrile, polyolefin and the like. These can be used alone or as a mixture.
- the coloring composition of the present invention is easily prepared by mixing, for example, so as to be 100 to 2,000 parts of a synthetic resin (nonvolatile content) per 100 parts of the phthalocyanine compound of the present invention, depending on the coloring application. I can do it.
- the average particle diameter of primary particles is measured as follows. First, the particle
- NMR analysis Nuclear magnetic resonance apparatus “JNM-LA300” manufactured by JEOL Ltd., using TMS as an internal standard substance
- Infrared spectroscopic analysis Infrared spectrophotometer “FT / IR-4200” manufactured by JASCO Corporation FD / MS analysis: mass spectrometer “JMS-700” manufactured by JEOL Ltd.
- UV-Vis spectrophotometry Spectrophotometer "U-4100” manufactured by Hitachi, Ltd.
- the obtained compound was subjected to 1 H- and 13 C-NMR analysis in dimethyl sulfoxide (hereinafter referred to as “DMSO”)-d6 solution, infrared spectroscopic analysis by KBr tablet method, and FD / MS analysis. However, the following analysis results were obtained.
- DMSO dimethyl sulfoxide
- [Pigment dispersion 1] 1.30 parts by mass of the phthalocyanine compound (14) obtained in Synthesis Example 3 is put in a polybin, 11.5 parts by mass of propylene glycol monomethyl ether acetate, DISPERBYK (trade name) LPN 21116 (manufactured by BYK Chemie Corp.) 3.62 Add parts by weight, 3.62 parts by weight of acrylic resin solution Unidic (registered trademark) ZL-295 manufactured by DIC Corporation, and 50 parts by weight of 0.3-0.4 mm ⁇ Sepul beads, and with a paint conditioner (manufactured by Toyo Seiki Co., Ltd.) Dispersed for 2 hours. To the obtained dispersion, 4.0 parts by mass of propylene glycol monomethyl ether acetate was added and dispersed for 30 minutes with a paint conditioner to obtain a pigment dispersion.
- DISPERBYK trade name
- LPN 21116 manufactured by BYK Chemie Corp.
- Paint conditioner manufactured by Toyo Seiki Co
- [Pigment dispersion 2] 1.25 parts by mass of the phthalocyanine compound (15) obtained in Synthesis Example 4 and 0.05 part by mass of Solsperse 5000 (manufactured by Nihon Lubrizol Co., Ltd.) are placed in a plastic bottle, 11.5 parts by mass of propylene glycol monomethyl ether acetate, DISPERBYK (trademark) Name) 3.62 parts by mass of LPN 21116 (manufactured by Big Chemie Co., Ltd.), 3.62 parts by mass of acrylic resin solution Unidic (registered trademark) ZL-295 manufactured by DIC Corporation, 50 0.3-0.4 mm ⁇ sepul beads 50 Mass parts were added and dispersed for 2 hours with a paint conditioner (manufactured by Toyo Seiki Co., Ltd.). To the obtained dispersion, 4.0 parts by mass of propylene glycol monomethyl ether acetate was added and dispersed for 30 minutes with a paint conditioner to obtain a pigment dispersion.
- Pigment dispersion 3 In place of the phthalocyanine compound (14) obtained in Synthesis Example 3, the pigment dispersion was prepared in the same manner as Pigment Dispersion 1 except that the phthalocyanine compound synthesized according to the method of Example 3 described in Japanese Patent No. 496812 was used. Obtained.
- Pigment dispersion 4 In place of the phthalocyanine compound (15) obtained in Synthesis Example 4, the pigment dispersion was prepared in the same manner as in Pigment Dispersion 2, except that the phthalocyanine compound synthesized according to the method of Example 4 described in Japanese Patent No. 496812 was used. Obtained.
- Pigment dispersion 5 A pigment dispersion was obtained in the same manner as for Pigment Dispersion 1, except that Pigment Green 58 (A110 manufactured by DIC Corporation) was used instead of the phthalocyanine compound (14) obtained in Synthesis Example 3.
- the dispersion viscosity is dispersed with a viscometer (Toki Sangyo TVE-25 type viscometer), and dispersed with a particle size distribution measuring device (HORIBA dynamic light scattering particle size distribution measuring device LB-550). The results of measuring the particle size are shown in Table 1.
- the pigment dispersions 1 and 2 have a lower dispersion viscosity and a smaller dispersion particle size than the pigment dispersions 3 and 4.
- the pigment dispersion 4 had a high viscosity, and the dispersed particle size could not be measured.
- Pigment dispersion 1 was applied onto a glass substrate by a spin coater.
- the number of rotations of the spin coater was 600, 800, 1000, and 1200 rpm, and four types of glass plates having different coating film thicknesses of the composition were prepared. Each glass plate coated with the composition thus obtained was heated at 90 ° C. for 3 minutes to obtain a color filter green pixel portion.
- a green pixel portion was obtained in the same manner as in Example 1 except that the pigment dispersion 2 was used instead of the pigment dispersion 1.
- the pigment dispersion 4 had a high viscosity and could not be uniformly applied to the glass substrate with a spin coater.
- Color filter evaluation test example Table 2 shows chromaticity and luminance values after post-baking (baking at 230 ° C. for 1 hour) and color difference values before and after post-baking of the color filters prepared in Examples and Comparative Examples. Chromaticity and luminance were measured using a spectrophotometer CM-3500d manufactured by Konica Minolta Co., Ltd., and contrast was measured using a contrast tester CT-1 / DULBM manufactured by Aisaka Electric Co., Ltd.
- Example 1 is superior to Comparative Example 1 in both luminance and contrast. Moreover, Example 2 was able to produce the coating film for evaluation unlike Comparative Example 2.
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Abstract
Description
また、一般式(1)中、Mは2~4価の金属原子(但し金属原子は酸化されていてもよい)を表す。)
供する。
前記化合物(1)又は化合物(2)を合成するためには、まず、その中間体であるN,N’-二置換イミダゾロン環を有するジニトリル化合物である下記一般式(3)で表されるジシアノベンツイミダゾロン化合物、又は下記一般式(4)で表される無水フタル酸およびフタルイミド化合物を下記の合成方法により合成する。
また化合物(7)は4-ブロモ-5-ニトロフタロニトリル(10)の臭素原子をアミンで置換することでも合成できる。この方法の詳細についてはメンデレーエフ コミュニケーションズ(Mendeleev Communications),78(2000)に記載されている。
本発明の化合物(1)は前記合成法により得られる化合物(3)又は化合物(4)と、前記一般式(1)中のMで表される2~4価の金属原子に対応する金属塩とを有機溶媒中、120~250℃で加熱縮合することによって得ることができる。
また本発明ではR1とR2、R3とR4、R5とR6、R7とR8はそれぞれ異なる基を表す。置換基を非対称化することでR1~R8がすべて同一である場合と比較して顔料粒子の凝集性が低下し、分散性が向上して分散液粘度が大きく低下したと考えられる。
赤外分光分析:日本分光株式会社製赤外分光光度計「FT/IR-4200」
FD/MS分析:日本電子株式会社製質量分析計「JMS-700」
紫外可視分光分析:株式会社日立製作所製分光光度計「U-4100」
(前記一般式(3)においてR9がエチル基、R10が水素であるジシアノベンツイミダゾロン化合物中間体の合成 ) 窒素雰囲気下、フラスコ中に4-アミノ-5-エチルアミノフタロニトリル 26.0gと1,1‘-カルボニルジイミダゾール 28.0gを量りとり、アセトニトリル(脱水) 260mlを加えて加熱還流した。6時間攪拌後、加熱を停止して反応液を室温まで冷却した。生成した沈殿をろ過し、アセトニトリルで洗浄後、90℃で1晩送風乾燥して式(12)で表される化合物23.7gを得た。(収率80%)
1H-NMR(DMSO-d6)δppm:1.19(t,j=7.2Hz,3H)、3.87(q,j=7.2Hz,2H)、7.65(s,1H)、8.00(s,1H)。
13C-NMR(DMSO-d6)δppm:13.3、35.5、106.7、106.8、112.5、113.2、116.8、116.9、131.9、133.3、153.9。
<赤外分光分析>
3250(N-H伸縮振動)、3056(エチル基C-H伸縮振動)、2239(シアノ基CN伸縮振動)、1737(カルボニル基CO伸縮振動)cm-1。
<FD/MS分析>
212M+
(前記一般式(3)においてR9がエチル基、R10がメチル基であるジシアノベンツイミダゾロン化合物の合成)
合成例2で得られた化合物について、DMSO-d6溶液中での1H-および13C-NMR分析、KBr錠剤法での赤外分光分析、FD/MS分析を行ったところ下記の分析結果が得られた。
1H-NMR(DMSO-d6):1.20(t,j=7.1Hz,3H)、3.38(s,3H)、3.92(q,j=7.1Hz,2H)、7.99(s,1H)、8.06(s,1H)。
13C-NMR(DMSO-d6):δ13.3,27.6,36.1,106.7,106.8,112.5,112.7,116.8,132.0,133.1,153.4
3070、2930(エチル基・メチル基C-H伸縮振動)、2230(シアノ基CN伸縮振動)、1718(カルボニル基CO伸縮振動)cm-1。
<FD/MS分析>
226M+
(フタロシアニン化合物(14)の合成)
窒素雰囲気下、1-ペンタノール110ml中に合成例2で得た化合物(13)11.0g、酢酸亜鉛2.33gおよび1,8-ジアザビシクロ[5,4,0]ウンデカ-7-エン(DBU)7.40gを添加し、攪拌しながら8時間加熱還流した。反応液を70℃以下に冷却後、析出した沈殿をろ過分離した。得られた粗生成物を熱メタノール、1mol/l塩酸水、7質量%アンモニア水、熱N,N-ジメチルホルムアミド、メタノールの順で洗浄し、目的のフタロシアニン化合物(14)8.84gを緑色固体として得た。(収率75%)。
合成例3で得られた化合物について、FD/MS分析、KBr錠剤法による赤外分光分析を行ったところ、下記の分析結果が得られた。
968M+
<赤外分光分析>
1695(カルボニル基CO伸縮振動)、1490、1415、1080cm-1
(フタロシアニン化合物(15)の合成)
窒素雰囲気下、1-ペンタノール100ml中に合成例2で得た化合物(13)9.90g、塩化銅(I)1.18gおよび1,8-ジアザビシクロ[5,4,0]ウンデカ-7-エン(DBU)6.81gを添加し、攪拌しながら8時間加熱還流した。反応液を70℃以下に冷却後、析出した沈殿をろ過分離した。得られた粗生成物を熱メタノール、1mol/l塩酸水、7質量%アンモニア水、熱N,N-ジメチルホルムアミド、メタノールの順で洗浄し、目的のフタロシアニン化合物(15)8.67gを緑色固体として得た。(収率82%)。
合成例4で得られた化合物について、FD/MS分析、KBr錠剤法による赤外分光分析を行ったところ、下記の分析結果が得られた。
<FD/MS分析>
967M+
<赤外分光分析>
1715(カルボニル基CO伸縮振動)、1490、1440、1420、1080cm-1
(フタロシアニン化合物(16)の合成)
窒素雰囲気下、1-ペンタノール100ml中に合成例2で得た化合物(13)10.0gおよび1,8-ジアザビシクロ[5,4,0]ウンデカ-7-エン(DBU)7.40gを添加し、攪拌しながら9時間加熱還流した。反応液を70℃以下に冷却後、析出した沈殿をろ過分離した。得られた粗生成物を熱メタノール、1mol/l塩酸水、7質量%アンモニア水、熱N,N-ジメチルホルムアミド、メタノールの順で洗浄し、目的のフタロシアニン化合物(16)6.79gを緑色固体として得た。(収率68%)。
合成例4で得られた化合物について、FD/MS分析、KBr錠剤法による赤外分光分析を行ったところ、下記の分析結果が得られた。
<FD/MS分析>
906M+
<赤外分光分析>
1714(カルボニル基CO伸縮振動)、1495、1475、1073、1025cm-1
合成例3~5で得たフタロシアニン化合物0.50質量部を塩化ナトリウム1.50質量部、ジエチレングリコール0.75質量部とともに磨砕した。その後、この混合物を600質量部の温水に投じ、1時間攪拌した。水不溶分をろ過分離して温水でよく洗浄した後、90℃で送風乾燥して顔料化を行った。顔料の粒子系は、300nm以下、粒子の平均長さ/幅比は3未満だった。得られたフタロシアニン化合物の緑色顔料を用いて以下の分散試験およびカラーフィルタ評価試験を行った。
合成例3で得たフタロシアニン化合物(14)1.30質量部をポリビンに入れ、プロ ピレングリコールモノメチルエーテルアセテート11.5質量部、DISPERBYK( 商標名)LPN 21116(ビックケミー株式会社社製)3.62質量部、DIC(株)製アクリル樹脂溶液ユニディック(登録商標)ZL-295 3.62質量部、0.3-0.4mmφセプルビーズ50質量部を加え、ペイントコンディショナー(東洋精機株式会社製)で2時間分散した。得られた分散体にプロピレングリコールモノメチルエーテ ルアセテート4.0質量部を添加してペイントコンディショナーでさらに30分間分散し顔料分散体を得た。
合成例4で得たフタロシアニン化合物(15)1.25質量部、Solsperse5000(日本ルーブリゾール株式会社製)0.05質量部をポリビンに入れ、プロピレングリコールモノメチルエーテルアセテート11.5質量部、DISPERBYK(商標名)LP N 21116(ビックケミー株式会社社製)3.62質量部、DIC(株)製アクリル樹脂溶液ユニディック(登録商標)ZL-295 3.62質量部、0.3-0.4mmφセプルビーズ50質量部を加え、ペイントコンディショナー(東洋精機株式会社製)で2時間分散した。得られた分散体にプロピレングリコールモノメチルエーテルアセテート4.0質量部を添加してペイントコンディショナーでさらに30分間分散し顔料分散体を得た。
合成例3で得たフタロシアニン化合物(14)に代えて特許第4962812号公報記載の実施例3の方法に従って合成したフタロシアニン化合物を用いた以外は、顔料分散体1と同様の方法で顔料分散体を得た。
合成例4で得たフタロシアニン化合物(15)に代えて特許第4962812号公報記載の実施例4の方法に従って合成したフタロシアニン化合物を用いた以外は、顔料分散体2と同様の方法で顔料分散体を得た。
合成例3で得たフタロシアニン化合物(14)に代えてPigment Green 58(DIC(株)製A110)を用いた以外は、顔料分散体1と同様の方法で顔料分散体を得た。
得られた分散体について、粘度計(東機産業TVE-25形粘度計)で分散液粘度を、粒径分布測定装置(HORIBA製動的光散乱式粒径分布測定装置LB-550)で分散粒径を測定した結果を表1に示す。
顔料分散体1の代わりに顔料分散体3を用いた以外は、実施例1と同様と同様の方法で緑色画素部を得た。
顔料分散体4は粘度が高く、スピンコーターでガラス基板に均一に塗布することができなかった。
実施例、比較例で作成したカラーフィルタの、ポストベーク(230℃、1時間焼成)後の色度、輝度の値とポストベーク前後の色差の値を表2に記載した。色度、輝度の測定はコニカミノルタ株式会社製分光測色計CM-3500d、コントラストの測定は壺坂電機株式会社製コントラストテスターCT-1/DULBMを使用した。
顔料分散体1の代わりに顔料分散体5を用いた以外は、実施例1と同様と同様の方法で緑色画素部を得た。
Claims (7)
- 前記一般式(1)において、Mで表される2~4価の金属原子が銅又は亜鉛である請求項1に記載のフタロシアニン化合物。
- 前記一般式(1)又は一般式(2)において、R1~R8が各々独立して炭素原子数1~4のアルキル基であり、但し、R1とR2、R3とR4、R5とR6、R7とR8は、それぞれ異なる基を表す、請求項1または2記載のフタロシアニン化合物。
- 前記一般式(3)および一般式(4)で表される化合物から選ばれた1つ以上の化合物単独もしくは前記一般式(1)中のMで表される2~4価の金属原子に対応する金属塩との混合物を熱縮合させることを特徴とする請求項1~3記載のいずれか1項記載のフタロシアニン化合物の製造方法。
- 請求項1~3いずれか1項記載のフタロシアニン化合物を含有することを特徴とするカラーフィルタ。
- 請求項1~3いずれか1項記載のフタロシアニン化合物を含有することを特徴とする着色組成物。
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