Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/17—Amines; Quaternary ammonium compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
  • C08K5/0041—Optical brightening agents, organic pigments
• • G—PHYSICS
  • G02—OPTICS
  • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
  • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
  • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
  • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
  • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
  • G02F1/1333—Constructional arrangements; Manufacturing methods
  • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
• • G—PHYSICS
  • G02—OPTICS
  • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
  • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
  • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
  • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
  • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
  • G02F1/1333—Constructional arrangements; Manufacturing methods
  • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
  • G02F1/133509—Filters, e.g. light shielding masks
  • G02F1/133514—Colour filters

Definitions

• the present invention relates to a colored curable resin composition, a color filter, and a display device.
• Display devices such as liquid crystal display devices, electroluminescence display devices, and plasma displays, and color filters used in solid-state image pickup devices such as CCDs and CMOS sensors are made of a colored curable resin composition.
• a color-curable resin composition a composition containing only a compound represented by the following formula as a coloring agent is known.
• the color filter formed from the conventionally known colored curable resin composition does not satisfy the brightness.
• the color filter formed of the above-mentioned conventionally known colored curable resin composition can not satisfy the light resistance.
• the gist of the present invention is as follows.
• a colorant comprising a colorant, a resin, a polymerizable compound and a polymerization initiator
• the colorant comprises a compound represented by the formula (I) and a red pigment (excluding the compound represented by the formula (I)),
• the content of the red pigment is 1% by mass or more and 95% by mass or less based on the total amount of the colorant.
• Each of R 1 to R 10 independently represents a hydrogen atom, a halogen atom, or a saturated hydrocarbon group having 1 to 8 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom.
• R 11 to R 16 each independently represent a hydroxyl group, a halogen atom, a cyano group, a nitro group, a saturated hydrocarbon group having 1 to 8 carbon atoms, a phenyl group or a benzyl group, and the hydrogen atom contained in the saturated hydrocarbon group,
• a cyano group, a nitro group, a hydroxyl group or a halogen atom, and the hydrogen atom contained in the phenyl group and the benzyl group may be substituted with a saturated hydrocarbon group having 1 to 4 carbon atoms, a halogen atom, a cyano group or a vinyl group .
• R 11 and R 12 , R 13 and R 14, and R 15 and R 16 may be connected to form a 3- to 6-membered heterocyclic ring containing a nitrogen atom,
• R 1 and R 11 , R 2 and R 12 , R 4 and R 13 , R 5 and R 14 , R 8 and R 15 , R 10 and R 16 , R 7 and R 8 and R 9 and R 10 are each To form a 6-membered ring.
• a q- represents an anion of q, and q represents an integer of 1-14.
• p represents the coefficient that the compound represented by the formula (I) holds the charge neutral.
• a colorant comprising a colorant, a resin, a polymerizable compound and a polymerization initiator
• the colorant comprises a compound represented by the formula (I) and a red pigment (excluding the compound represented by the formula (I)),
• the content of the red pigment is 30 mass% or more and 95 mass% or less with respect to the total amount of the coloring agent.
• Each of R 1 to R 10 independently represents a hydrogen atom, a halogen atom, or a saturated hydrocarbon group having 1 to 8 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom.
• R 11 to R 16 each independently represent a hydroxyl group, a halogen atom, a cyano group, a nitro group, a saturated hydrocarbon group having 1 to 8 carbon atoms, a phenyl group or a benzyl group, and the hydrogen atom contained in the saturated hydrocarbon group
• a nitro group, a hydroxyl group or a halogen atom, and the hydrogen atom contained in the phenyl group and the benzyl group may be substituted with a saturated hydrocarbon group having 1 to 4 carbon atoms, a halogen atom, a cyano group or a vinyl group.
• R 11 and R 12 , R 13 and R 14, and R 15 and R 16 may be connected to form a 3- to 6-membered heterocyclic ring containing a nitrogen atom,
• R 1 and R 11 , R 2 and R 12 , R 4 and R 13 , R 5 and R 14 , R 8 and R 15 , R 10 and R 16 , R 7 and R 8 and R 9 and R 10 are each To form a 6-membered ring.
• a q- represents an anion of q, and q represents an integer of 1-14.
• p represents the coefficient that the compound represented by the formula (I) holds the charge neutral.
• a q- is an anion containing at least one atom selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and an oxygen atom, a halide anion, a perchlorate ion, a chlorate ion, a thiocyanate ion,
• the metal ion is selected from the group consisting of a metal ion, a borate ion, a hexafluoroantimonate ion, a tetrafluoroborate ion, an organic carbonic acid anion, an organic sulfonic acid anion, an organic phosphate anion, an organic imidic acid anion, ] Or [2].
• a display device comprising the color filter according to [5].
• a color filter excellent in lightness can be formed. Further, according to the colored curable resin composition of the present invention, a color filter excellent in light resistance can be formed.
• the colored curable resin composition of the present invention is a colored curable resin composition comprising a colorant (hereinafter may be referred to as a colorant (A)), a resin (hereinafter sometimes referred to as a resin (B) ), And a polymerization initiator (hereinafter sometimes referred to as a polymerization initiator (D)).
• a colorant hereinafter may be referred to as a colorant (A)
• a resin hereinafter sometimes referred to as a resin (B)
• a polymerization initiator hereinafter sometimes referred to as a polymerization initiator (D)
• the colorant (A) comprises a compound represented by the formula (I) and a red pigment (excluding the compound represented by the formula (I)), wherein the content of the red pigment is 1% by mass or more to 95% % Or less.
• the colored curable resin composition of the present invention preferably further contains a solvent.
• the colored curable resin composition of the present invention may contain a leveling agent.
• the colorant (A) includes a compound represented by the formula (I) and a red pigment (excluding the compound represented by the formula (I)).
• the compound represented by the formula (I) is as follows.
• Each of R 1 to R 10 independently represents a hydrogen atom, a halogen atom, or a saturated hydrocarbon group having 1 to 8 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom.
• R 11 to R 16 each independently represent a hydroxyl group, a halogen atom, a cyano group, a nitro group, a saturated hydrocarbon group having 1 to 8 carbon atoms, a phenyl group or a benzyl group, and the hydrogen atom contained in the saturated hydrocarbon group
• a nitro group, a hydroxyl group or a halogen atom, and the hydrogen atom contained in the phenyl group and the benzyl group may be substituted with a saturated hydrocarbon group having 1 to 4 carbon atoms, a halogen atom, a cyano group or a vinyl group.
• R 11 and R 12 , R 13 and R 14, and R 15 and R 16 may be connected to form a 3- to 6-membered heterocyclic ring containing a nitrogen atom,
• R 1 and R 11 , R 2 and R 12 , R 4 and R 13 , R 5 and R 14 , R 8 and R 15 , R 10 and R 16 , R 7 and R 8 and R 9 and R 10 are each To form a 6-membered ring.
• a q- represents an anion of q, and q represents an integer of 1-14.
• p represents the coefficient that the compound represented by the formula (I) holds the charge neutral.
• the saturated hydrocarbon group having 1 to 8 carbon atoms representing R 1 to R 10 and R 11 to R 16 may be any of straight chain, branched chain and cyclic.
• Examples of the linear or branched saturated hydrocarbon group include straight chain alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group and octyl group; isopropyl group, isobutyl group, isopentyl group, neopentyl group , And a branched chain alkyl group such as a 2-ethylhexyl group.
• the number of carbon atoms in the saturated hydrocarbon group is preferably 1 to 6, more preferably 1 to 4.
• the cyclic saturated hydrocarbon group may be monocyclic or polycyclic.
• Examples of the cyclic saturated hydrocarbon group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
• the number of carbon atoms in the cyclic saturated hydrocarbon group is preferably 3 to 8, and more preferably 6 to 8.
• a straight chain saturated hydrocarbon group is preferable, and a methyl group, an ethyl group and a propyl group are particularly preferable.
• the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom.
• halogen atom examples include fluorine, chlorine, bromine and iodine.
• a halogen atom is substituted as in the case of forming a perfluoroalkyl unit such as a trifluoromethyl unit, a pentafluoroethyl unit, or a heptafluoropropyl unit.
• the hydrogen atom contained in the saturated hydrocarbon group having 1 to 8 carbon atoms may be substituted with a cyano group, a nitro group, a hydroxyl group, or a halogen atom.
• the hydrogen atom contained in the phenyl group and the benzyl group may be substituted with a saturated hydrocarbon group having 1 to 4 carbon atoms, a halogen atom, a cyano group, or a vinyl group.
• the saturated hydrocarbon group having 1 to 4 carbon atoms which may be substituted with the hydrogen atom included in the phenyl group and the benzyl group represented by R 11 to R 16 includes the same saturated hydrocarbon group having 1 to 4 carbon atoms as the saturated hydrocarbon group having 1 to 8 carbon atoms .
• R 1 and R 11 , R 2 and R 12 , R 4 and R 13 , R 5 and R 14 , R 8 and R 15 , R 10 and R 16 , R 7 and R 8 and R 9 and R 10 are each To form a 6-membered ring.
• 6-membered ring examples include a benzene ring, a piperidine ring, a pyridine ring, a phylimidine ring, a quinoline ring, and an isoquinoline ring.
• R 11 and R 12 , R 13 and R 14, and R 15 and R 16 may be linked together to form a 3- to 6-membered heterocyclic ring containing a nitrogen atom.
• Examples of the 3- to 6-membered heterocyclic ring include pyrrolidine ring, morpholine ring, piperidine ring, piperazine ring, thiomorpholine ring, pyrrole ring, imidazole ring, imidazolidine ring, pyrazolidine ring, Nitrogen-containing heterocycle such as pyridine ring, pyridine ring and the like, and preferably nitrogen-containing aliphatic heterocycle having only one nitrogen atom as a hetero atom such as pyrrolidine ring and piperidine ring.
• R 1 to R 6 , R 8 and R 10 are each independently a hydrogen atom
• R 7 and R 9 are each independently a hydrogen atom or a halogen atom
• R 11 to R 16 each independently represent a hydrogen atom
• R 1 to R 6 , R 8 and R 10 is independently a hydrogen atom
• R 7 and R 9 are each independently a halogen atom
• R 11 to R 16 are each independently an alkyl group having 1 to 6 carbon atoms Of saturated hydrocarbon groups.
• a q- is an anion of q, and an anion of any one of 1 to 14.
• q represents 1 to 14, preferably 1 to 6, more preferably 1 to 4, further preferably 1 to 3, and particularly preferably 1 or 2.
• p represents the coefficient that the compound represented by the formula (I) holds the charge neutral. Specifically, p is 1 to 14, preferably 1 to 6, more preferably 1 to 4, still more preferably 1 to 3, and particularly preferably 1 or 2.
• anion examples include halide anion, other inorganic anion, organic carbonic acid anion, organic sulfonic acid anion, organic phosphate anion, organic imidic acid anion, organic methidic acid anion, and metal complex anion.
• halide anion examples include a chloride ion, a bromide ion, an iodide ion, and a fluoride ion.
• inorganic anion examples include a perchlorate ion, a chlorate ion, a thiocyanate ion, a hexafluorophosphate ion (hereinafter also referred to as "anion VII"), a hexafluoroantimonic acid ion, a tetrafluoroborate ion, .
• Examples of the inorganic anion include anions containing at least one atom selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and an oxygen atom. From the viewpoint of heat resistance, anions containing tungsten atoms and oxygen atoms are preferred.
• anion containing at least one atom selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and an oxygen atom examples include? - [PW 12 O 40 ] 3- (hereinafter also referred to as "anion (IX) Tungstate ions such as? - [P 2 W 18 O 62 ] 6- and? - [P 2 W 18 O 62 ] 6- ; tungstate ions such as ⁇ - [SiW 12 O 40 ] 4-, ⁇ - [SiW 12 O 40] 4-, ⁇ - [SiW 12 O 40] 4- , etc.
• Kane ginhyeong silicon tungstate ions [P 2 W 17 O 61 ] 10-, [P 2 W 15 O 56] 12-, [H 2 P 2 W 12 O 48] 12-, [NaP 5 W 30 O 110] 14-, ⁇ - [SiW 9 O 34] 10-, ⁇ - [SiW 10 O 36] 8 -, ⁇ - [SiW 11 O 39 ] 8-, ⁇ - [SiW 11 O 39] 8-; [W 6 O 19] 2-, [W 10 O 32] containing tungsten such as 4-, WO 4 2- An isophosphoric acid ion, a silicate ion, and a phosphate ion.
• organic carbonic acid anion examples include acetic acid ion and the like.
• organic sulfonic acid anion examples include methanesulfonate ion, dodecylsulfonate ion, benzenesulfonate ion, toluenesulfonate ion, naphthalenesulfonate ion, diphenylamine-4-sulfonate ion, 2- A 2-amino-5-nitrobenzenesulfonic acid ion, a phthalocyanine sulfonic acid ion, a sulfonic acid ion having a polymerizable substituent, a benzene disulfonic acid anion, and a naphthalene disulfonic acid anion.
• organic phosphate anion examples include octyl phosphate ion, dodecyl phosphate ion, octadecyl phosphate ion, phenyl phosphate ion, nonylphenyl phosphate ion, 2,2'-methylenebis (4,6-di-t-butylphenyl) And the like.
• the metal complex anion is an anion that complexes a metal atom with a molecule containing a group capable of complexing with a metal atom in the molecule.
• Examples of the metal complex anion include CI Solvent Yellow 13, 19, 21, 25, 25: 1, 62, 79, 81, 82, 83, 83: 1, 88, 89, 90, 151, CI Solvent Red 8, 35, 83: 1, 84: 1, 90, 90: 1, CI Solvent Violet 2, 21, 21: 1, 46, 49, 49, 51, 51, 51, , 58, 61, CI Solvent Blue 137, CI Solvent Brown 28, 42, 43, 44, 53, 62, 63, CI Acid Yellow 59, 121, CI Acid Orange 74, 162, CI Acid Red 211, And anions derived from the metal complex salt dyes described in JP-A-170117.
• Examples of the molecule (ligand) include azo molecules and methine molecules, and azo molecules are preferred.
• Examples of the metal atom include chromium, cobalt, and nickel, and chromium and cobalt are preferable.
• metal complex anion examples include anions represented by the formula (VIII).
• a q- is preferably an anion containing at least one atom selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and an oxygen atom, an organic carbonic acid anion, an organic sulfonic acid anion, an organic imidic acid anion, Acid anions and metal complex anions are preferable, and anion and metal complex anions containing at least one atom selected from the group consisting of tungsten, molybdenum, silicon and phosphorus and an oxygen atom are more preferable.
• a fluorine-containing organic acid anion a fluorine-containing organic sulfonic acid anion, a fluorine-containing organic imidic acid anion and a fluorine-containing organic acid anion (hereinafter collectively referred to as a fluorine anion) are more preferable.
• fluorine anions examples include CF 3 CO 2 - and anions represented by formulas (III), (IV), (V) or (VI).
• W 3 and W 4 independently represent a fluorine atom or an alkyl fluoride group having 1 to 4 carbon atoms or W 3 and W 4 together form an alkyl fluoride group having 1 to 4 carbon atoms Represents a diary.
• W 5 to W 7 independently represent a fluorine atom or an alkyl fluoride group having 1 to 4 carbon atoms.
• Y 1 represents a fluorinated alkanediyl group having 1 to 4 carbon atoms.
• Y 2 represents an alkyl fluoride group having 1 to 4 carbon atoms.
• a perfluoroalkyl group is preferable as the fluorinated alkyl group having 1 to 4 carbon atoms.
• a perfluoroalkyl group is preferable. Examples in the art perfluoroalkyl group, -CF 3, -CF 2 CF 3 , -CF 2 CF 2 CF 3, -CF (CF 3) 2, -CF 2 CF 2 CF 2 CF 3, -CF 2 CF (CF 3 ), and the 2, -C (CF 3) 3.
• a perfluoroalkanediyl group is preferable, and -CF 2 -, -CF 2 CF 2 -, -CF 2 CF 2 CF 2 -, -C (CF 3 ) 2 -, -CF 2 CF 2 CF 2 CF 2 - and the like.
• anion (III) examples include anions represented by the formulas (III-1) to (III- Quot; to " anion (III-6) ").
• anion (IV) examples include the anion (IV-1) represented by the formula (IV-1).
• anions (V-1) to (V-4) (hereinafter, referred to as "anions (V-1)" - " anion (V-4) ").
• anions represented by the formulas (VI-1) to (VI-4) (hereinafter, referred to as "anions (VI-1)") as the anions represented by the formula (VI) - " anion (VI-4) ").
• the fluorine anion may be at least one anion selected from the group consisting of CF 3 CO 2 - , anion (III), anion (IV), anion (V) and anion (VI).
• CF 3 CO 2 - an anion (III-1), anionic (III-2), anions (III-6), anions (IV-1), anionic (V-1), anionic (VI-1)
• the anion (VI-2) and the anion (VI-3) are preferable and the CF 3 CO 2 - , the anion (III-2), the anion (IV-1) and the anion (VI-1) are more preferable.
• the compound represented by the formula (I) is preferably a compound represented by the formula (I-A).
• Me is a methyl group
• Et is an ethyl group
• Pro is a propyl group
• III-1 to III-6 V-1, V-2, VII, VIII
• the compound represented by formula (I-A) is preferably a compound represented by formula (I-1) to formula (I-324).
• the compounds represented by formulas (I-97) to (I-192) and the compounds represented by formulas (I-289) to (I-324) are preferable, -128), compounds represented by formulas (I-289) to (I-324) are more preferable and compounds represented by formulas (I-97) to (I-120) ) To formula (I-324) are more preferable, and a compound represented by formula (I-104), a compound represented by formula (I-308) .
• the compound represented by the formula (I) can be prepared, for example, by referring to the method described in International Publication No. 2014/196464.
• the content of the compound represented by the formula (I) is preferably from 1 to 50 mass%, more preferably from 2 to 40 mass%, and still more preferably from 3 to 30 mass% More preferable.
• the content of the compound represented by the formula (I) is preferably 0.2 mass% or more and 20 mass% or less, more preferably 0.5 mass% or more and 15 mass% or less, and 1 mass% or more and 12 mass% or less More preferable.
• total solid content in the present specification means the amount excluding the content of the solvent from the total amount of the colored curable resin composition.
• the total solid content and the content of each component in the solid content can be measured by known analytical means such as liquid chromatography or gas chromatography.
• red pigment contained in the colored curable resin composition of the present invention known pigments can be used.
• red among the pigments classified as pigments in the color index (The Society of Dyers and Colourists), red .
• Two or more species may be used in combination.
• the compounds represented by the formula (I) are excluded.
• red pigments anthraquinone pigments, azo pigments, quinacridone pigments, perylene pigments and diketopyrrolopyrrole pigments are preferable, and C.I. Pigment Red 177, 179, 202, 208, 242, 254, 269, brominated diketopyrrolopyrrole pigments are preferred, and C.I. Pigment Red 177, 202, 254, 269, brominated diketopyrrolopyrrole pigments are more preferable.
• the content of the red pigment is preferably 1% by mass or more and 95% by mass or less, more preferably 30% by mass or more and 95% by mass or less, more preferably 40% by mass or more and 90% by mass or less relative to the total amount of the colorant, more preferably 50% And still more preferably at least 60% by mass.
• the RGB color pixels are stacked on the substrate, and the red, green, and blue R, G, For example, 1% by mass or more and 95% by mass or less (preferably 1% by mass or more and less than 30% by mass), a red colored coating film excellent in light resistance can be obtained.
• the total content of the compound represented by the formula (I) and the red pigment is preferably 40 mass% or more, more preferably 50 mass% or more, and preferably 100 mass% or less, relative to the total amount of the colorant.
• the total content of the compound represented by the formula (I) and the red pigment is preferably 40% by mass or more, Is not less than 50% by mass, preferably not more than 99% by mass, more preferably not more than 95% by mass.
• the content of the red pigment is preferably 0.1% by mass or more and 30% by mass or less, more preferably 1% by mass or more and 20% by mass or less, based on the whole solid content.
• the colored curable resin composition of the present invention may contain, as the colorant (A), a compound represented by the formula (I) and a colorant other than the red pigment (hereinafter sometimes referred to as a colorant (A1)).
• the colorant (A1) may contain one or two or more coloring agents.
• the colorant (A1) may be a dye or a pigment.
• the dyes include known dyes described in Color Index (published by The Society of Dyers and Colourists) and dyeing notes (Colored Yarn). According to the chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes (except compounds represented by formula (I)), cyanine dyes, naphthoquinone dyes, quinone imine dyes, , Azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes and phthalocyanine dyes. Of these, organic solvent-soluble dyes are preferred. These dyes may be used in combination of two or more.
• dyes having the following color index (CI) numbers can be mentioned.
• a known pigment can be used, and for example, a pigment classified as pigment in the color index (The Society of Dyers and Colourists) can be mentioned. Two or more species may be used in combination. Provided that the compound represented by the formula (I) is excluded.
• CI Pigment Yellow 1 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214;
• C.I. Orange pigments such as Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;
• C.I. Violet pigments such as Pigment Violet 1, 19, 23, 29, 32, 36, 38;
• colorant (A1) a yellow pigment is preferable, and C.I. Pigment Yellow 138, 139, 150, 185, and 231 are more preferable.
• the content thereof is preferably 1% by mass or more and 50% by mass or less, and more preferably 3% by mass or more and 45% by mass or less, based on the total amount of the colorant.
• the content of the yellow pigment is preferably 0.2% by mass or more and 25% by mass or less, and more preferably 0.6% by mass or more and 20% by mass or less, based on the entire solid content.
• the compound represented by the formula (I), the red pigment and the pigment in the colorant (A1) may be subjected to a rosin treatment, a coloring agent derivative into which an acidic group or a basic group has been introduced Surface treatment using a polymer compound, graft treatment to a surface such as a pigment such as a pigment, atomization treatment using a sulfuric acid atomization method and the like, cleaning treatment with an organic solvent or water for removing impurities, ion exchange treatment with ionic impurities, .
• the particle diameters of the pigment and the like are preferably substantially uniform.
• the pigment or the like is dispersed uniformly in the dispersion by carrying out dispersing treatment with a dispersant.
• a surfactant or the like can be enumerated, and any of cationic, anionic, nonionic or amphoteric surfactants may be used. Specific examples thereof include surfactants such as polyester-based, polyamine-based, and acrylic-based surfactants.
• a resin (B) described below may be used. These dispersants may be used alone or in combination of two or more.
• dispersing agent examples include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), fluorene (manufactured by Kyowa Chemical Industry Co., Ltd.), Solsperse (manufactured by Zeneca), EFKA (registered trademark) (Manufactured by BASF), ADISPER (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.) and Disperbyk (registered trademark) (manufactured by BICKEMISA) and BYK (registered trademark) (manufactured by BICKEMISA).
• the amount of the dispersing agent to be used is preferably 100 parts by mass or less, more preferably 5 parts by mass or more and 50 parts by mass or less, based on 100 parts by mass of the pigment and the like.
• the amount of the dispersing agent used is within the above range, there is a tendency to obtain a coloring agent-containing liquid in a more uniform dispersion state.
• the content of the colorant (A) in the colored curable resin composition is usually 10 to 60 mass%, preferably 12 to 55 mass%, more preferably 15 to 15 mass% 50% by mass or less.
• the resin (B) is not particularly limited, but is preferably an alkali-soluble resin, and at least one kind (a) (hereinafter referred to as "(a)") selected from the group consisting of an unsaturated carboxylic acid and an unsaturated carboxylic acid anhydride Is more preferable.
• the resin (B) may further contain a structural unit derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)") (Hereinafter sometimes referred to as " (c) ") which is copolymerizable with the monomer (c) (provided that (a) and (b) are different), and a structural unit derived from an ethylenically unsaturated bond Having at least one kind of structural unit selected from the group consisting of structural units having the above-mentioned structural units.
• a structural unit derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond hereinafter sometimes referred to as "(b)"
• &quot ethylenically unsaturated bond
• (meth) acrylic acid refers to at least one kind selected from the group consisting of acrylic acid and methacrylic acid.
• (b) is a monomer having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of oxirane rings, oxetane rings and tetrahydrofuran rings) and a monomer having a (meth) acryloyloxy group .
• (meth) acrylate vinylbenzyl glycidyl ether, 3,4-epoxy tricyclo [5.2.1.0 2,6 ] decyl (meth) acrylate, 3-ethyl (Meth) acryloyloxymethyl oxetane, tetrahydrofurfuryl (meth) acrylate and the like, and preferred examples thereof include glycidyl (meth) acrylate, 3,4-epoxy tricyclo [ 5.2.1.0 2,6 ] decyl (meth) acrylate, 3-ethyl-3- (meth) acryloyloxymethyloxetane.
• the resin having a structural unit having an ethylenically unsaturated bond in the side chain may be obtained by adding (b) to the copolymer of (a) and (c), or by adding (a) to the copolymer of (b) .
• the resin may be a resin obtained by adding (a) to a copolymer of (b) and (c) and further reacting with a carbonic anhydride.
• the weight average molecular weight of the resin (B) in terms of polystyrene is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and still more preferably 5,000 to 30,000.
• the molecular weight distribution (weight average molecular weight (Mw) / number average molecular weight (Mn)) of the resin (B) is preferably 1.1 to 6, and more preferably 1.2 to 4.
• the acid value of the resin (B) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, and still more preferably 70 to 135 mg-KOH / g in terms of solid content.
• the acid value is a value measured as the amount (mg) of potassium hydroxide necessary for neutralizing 1 g of the resin (B), and can be obtained by titration using, for example, an aqueous potassium hydroxide solution.
• the content of the resin (B) is preferably from 5 to 60% by mass, more preferably from 10 to 50% by mass, and still more preferably from 17 to 40% by mass, based on the whole solid content.
• the polymerizable compound (C) is a compound capable of being polymerized by an active radical and / or an acid generated from the polymerization initiator (D), for example, a compound having a polymerizable ethylenic unsaturated bond, Is a (meth) acrylic acid ester compound.
• the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenic unsaturated bonds.
• examples of such polymerizable compounds include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) Dipentaerythritol hexa (meth) acrylate, and the like.
• the weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 or more and 1,500 or less.
• the content of the polymerizable compound (C) is preferably 3 to 60 mass%, more preferably 5 to 50 mass%, and still more preferably 11 to 40 mass%, based on the entire solid content.
• the polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating an active radical or an acid by the action of light or heat and capable of initiating polymerization, and a known polymerization initiator can be used.
• Examples of the polymerization initiator that generates an active radical include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy- 2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan- 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutan-1-one, 1-hydroxycyclohexyl Phenyl ketone, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,2'
• the polymerization initiator is preferably a polymerization initiator comprising at least one member selected from the group consisting of a triazine compound, an acylphosphine oxide compound, an alkylphenone compound, an O-acyloxime compound and a nonimidazole compound, and O- A polymerization initiator comprising a compound is more preferable.
• the content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C).
• the content of the polymerization initiator (D) is within the above range, the sensitivity of the color filter tends to be shortened and the exposure time is shortened.
• the content of the O-acyloxime compound is preferably 50% by mass or more, more preferably 80% by mass or more, further preferably 90% by mass or more, and particularly preferably 90% by mass or more based on the total amount of the polymerization initiator (D) By mass is 95% by mass or more.
• the content of the O-acyloxime compound is within the above range, there is a tendency that a color filter having high sensitivity can be produced even when the sensitivity, developability and colorant content in forming a colored pattern are high.
• the colored curable resin composition of the present invention may contain a polymerization initiator.
• the polymerization initiator (D1) is a compound or a sensitizer used for promoting polymerization of a polymerizable compound initiated by polymerization initiator. When the polymerization initiator (D1) is included, it is usually used in combination with the polymerization initiator (D).
• Examples of the polymerization initiator (D1) include 4,4'-bis (dimethylamino) benzophenone (commonly referred to as Mihiraazuketone), 4,4'-bis (diethylamino) benzophenone, 9,10-dimethoxyanthracene, 2,4-diethyl thioxanthone N-phenylglycine, and the like.
• polymerization initiator (D1) When these polymerization initiator (D1) is used, its content is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, per 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C) Mass part. When the amount of the polymerization initiator (D1) is within this range, it is possible to form a colored pattern with higher sensitivity, and the productivity of the color filter tends to be improved.
• the colored curable resin composition of the present invention preferably contains a solvent.
• the solvent (E) is not particularly limited, and a solvent commonly used in the art can be used.
• a solvent commonly used in the art can be used.
• an ester solvent a solvent containing -COO- in the molecule and containing no -O-
• an ether solvent a solvent containing -O- and no -COO- in the molecule
• an ether ester Solvent containing -COO- and -O- in the molecule
• ketone solvent solvent containing -CO- in the molecule and not including -COO-
• alcohol solvent containing OH in the molecule, O-, -CO- and -COO-
• aromatic hydrocarbon solvents amide solvents, dimethylsulfoxide, and the like.
• ester solvents such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, n-butyl acetate, ethyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetone and ⁇ -butyrolactone
• ester solvents such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, n-butyl acetate, ethyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetone and ⁇ -butyrolactone
• Ethylene glycol monobutyl ether diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-1-butanol
• diethylene glycol Ether solvents such as dimethyl ether and diethylene glycol methyl ethyl ether (solvent
• Ether ester solvents such as methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate and diethylene glycol monoethyl ether acetate A solvent containing -COO- and -O-);
• Ketone solvents such as diacetone alcohol, 4-hydroxy-4-methyl-2-pentanone, heptanone, 4-methyl-2-pentanone, cyclohexanone Alcohol solvents such as butanol, cyclohexanol and propylene glycol (solvents containing OH in the molecule and containing no -O-, -CO- and -COO-), and the like .
• Aromatic hydrocarbon solvents such as benzene, toluene, xylene and mesitylene.
• Amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone.
• diacetone alcohol propylene glycol monomethyl ether acetate
• propylene glycol monomethyl ether propylene glycol monomethyl ether
• ethyl lactate propylene glycol monomethyl ether
• cyclohexanone ethyl 3-ethoxypropionate
• the solvent is preferably a mixed solvent containing propylene glycol monomethyl ether acetate.
• the solvent to be combined with propylene glycol monomethyl ether acetate include diacetone alcohol, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, dipropylene glycol methyl Methoxybutyl acetate, 3-methoxy-1-butanol and 4-hydroxy-4-methyl-2-pentanone are preferable, and diacetone alcohol, propylene glycol monomethyl ether, dipropylene glycol methyl Ethoxyacetate, ethyl lactate, 3-methoxybutyl acetate, 3-methoxy-1-butanol and ethyl 3-ethoxypropionate are more preferable, and diacetone alcohol, ethyl lactate, 4-hydroxy- - pentanone and propylene glycol monomethyl
• the content of the solvent in combination with propylene glycol monomethyl ether acetate is preferably 1% by mass or more and 50% by mass or less, more preferably 3% by mass or more and 40% by mass or less relative to the total amount of the solvent, 5 mass% or more and 30 mass% or less.
• the content of the solvent (E) is preferably 70 to 95% by mass, and more preferably 75 to 92% by mass, based on the total amount of the colored curable resin composition of the present invention.
• the total solid content of the colored curable resin composition is preferably 5 to 30% by mass, and more preferably 8 to 25% by mass.
• the colored curable resin composition of the present invention may contain additives known in the art such as leveling agents, fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents, if necessary.
• the colored curable resin composition of the present invention can be prepared by mixing a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), a solvent (E) .
• Examples of the method for producing a colored pattern with the colored curable resin composition of the present invention include a photolithographic method, an inkjet method, and a printing method. Among them, a photolithographic method is preferable. In the photolithographic method, a colored coating film which is a cured product of the colored composition layer can be formed by not using a photomask at the time of exposure and / or not developing it. The coloring pattern or colored coating film thus formed is the color filter of the present invention.
• the colored curable resin composition of the present invention can produce a color filter having excellent brightness.
• a color filter is useful as a color filter used in a display device (e.g., a liquid crystal display device, an organic EL device, an electronic paper, etc.) and a solid-state image pickup device.
• the mixture was kept at 0 ⁇ and stirred for 5 hours to complete the reaction, followed by filtration of the solid component.
• the solid component was washed repeatedly with methanol and water until the color of the filtrate was removed and precipitation of the salt was eliminated. Thereafter, the solid content was dried in a vacuum drier at 80 DEG C for 18 hours to obtain the aimed red pigment 1.
• the yield was 107 parts.
• a flask equipped with a reflux condenser, a dropping funnel and a stirrer was charged with an appropriate amount of nitrogen and replaced with a nitrogen atmosphere. Then, 141 parts of ethyl lactate and 178 parts of propyleneglycol monomethylether acetate were added and heated to 85 ⁇ with stirring.
• Resin (B-1) has the following structural unit.
• the weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin were measured by the GPC method under the following conditions.
• TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 manufactured by Tosoh Corporation
• the ratio (Mw / Mn) of the weight average molecular weight and the number average molecular weight in terms of polystyrene obtained as described above was dispersed.
• Resin (B-1) Resin B-1 (in terms of solid content)
• Polymerizable compound (C-1) dipentaerythritol hexaacrylate ("A9550", produced by Shin-Nakamura Chemical Co., Ltd.)
• Polymerization initiator (D-1) N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (Irgacure (registered trademark) OXE 01,
• Leveling agent (F-1) polyether-modified silicone oil (in terms of solid content) (Toray Silicone SH8400, manufactured by Toray Dow Corning Co., Ltd.)
• the colored curable resin composition was coated on a glass substrate (Eagle 2000; Corning) having a 5 cm edge by a spin coating method, and then prebaked at 100 ⁇ ⁇ for 3 minutes to form a coloring composition layer. After cooling, the coloring composition layer was irradiated with light at an exposure amount of 60 mJ / cm 2 (365 nm standard) in an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.). Thereafter, post-baking was performed in an oven at 230 ⁇ for 20 minutes to obtain a color filter.
• the film thickness of the obtained color filter was measured using a film thickness measuring device (DEKTAK3; manufactured by Japan Vacuum Technology Co., Ltd.). The results are shown in Table 13.
• the obtained color filter was measured for spectroscopy using a colorimeter (OSP-SP-200, manufactured by Olympus Corporation), and the xy chromaticity coordinates (x, y) of the CIE XYZ table colorimeter, y) and stimulus value Y were measured.
• OSP-SP-200 manufactured by Olympus Corporation
• xy chromaticity coordinates (x, y) of the CIE XYZ table colorimeter, y) and stimulus value Y were measured.
• the larger the value of Y the higher the brightness.
• Table 13 The results are shown in Table 13.
• the xy chromaticity coordinates (x, y) and Y were measured before and after the irradiation, and the color difference DELTA Eab * was calculated from the measured values by the method described in JIS Z 8730: 2009 (Method for calculating color difference) .
• the colored pattern made of the same colored curable resin composition can also be said to have good light resistance.
• a color filter excellent in lightness can be formed. Further, according to the colored curable resin composition of the present invention, a color filter excellent in light resistance can be formed.

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• 2018
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