WO2019177401A1 - Composé, composition de résine colorée, filtre coloré et dispositif d'affichage - Google Patents

Composé, composition de résine colorée, filtre coloré et dispositif d'affichage Download PDF

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Publication number
WO2019177401A1
WO2019177401A1 PCT/KR2019/002981 KR2019002981W WO2019177401A1 WO 2019177401 A1 WO2019177401 A1 WO 2019177401A1 KR 2019002981 W KR2019002981 W KR 2019002981W WO 2019177401 A1 WO2019177401 A1 WO 2019177401A1
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parts
formula
group
mass
compound
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PCT/KR2019/002981
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English (en)
Korean (ko)
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우에다토시오
쇼타모리와키
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동우 화인켐 주식회사
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Priority claimed from JP2018240241A external-priority patent/JP7101111B2/ja
Application filed by 동우 화인켐 주식회사 filed Critical 동우 화인켐 주식회사
Priority to KR1020207020600A priority Critical patent/KR20200122300A/ko
Priority to CN201980019574.4A priority patent/CN111886296B/zh
Publication of WO2019177401A1 publication Critical patent/WO2019177401A1/fr

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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
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/007—Squaraine 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
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • 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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

Definitions

  • the present invention relates to a compound, a colored resin composition, a color filter, and a display device.
  • the color filter used for display apparatuses such as a liquid crystal display device, an electroluminescence display device, and a plasma display, and solid-state image sensors, such as a CCD and a CMOS sensor, is manufactured with a colored resin composition.
  • a coloring agent used for such a colored resin composition the compound represented by Formula (x) is known.
  • Patent Document 1 Japanese Unexamined Patent Publication No. 2015-86380
  • the color filter formed from the colored resin composition containing the said compound conventionally known may not fully satisfy heat resistance. Therefore, this invention provides the compound which can form the color filter excellent in heat resistance.
  • This invention includes the following inventions.
  • R 1 to R 8 each independently represent a hydrogen atom, a hydroxy group, a C 1-20 alkyl group which may have a substituent, or a C 1-20 alkoxy group which may have a substituent.
  • R 9 to R 12 each independently represent a C 1-20 hydrocarbon group which may have a substituent
  • at least one of R 9 to R 12 is a C 1-20 aliphatic hydrocarbon group having a carboxy group as a substituent
  • at least one of R ⁇ 9> -R ⁇ 12> may be a C6-C20 aromatic hydrocarbon group which may have a substituent
  • the methylene group contained in the said aliphatic hydrocarbon group may be substituted by -O-.
  • a colored resin composition comprising a colorant and a resin, wherein the colorant comprises a compound represented by Formula (I) according to [1].
  • a display device comprising the color filter described in [4].
  • the novel compound which can form the color filter excellent in heat resistance is provided.
  • the compound which concerns on this invention is a compound represented by Formula (I) (henceforth a compound (I)).
  • Formula (I) contains the resonance structure of Formula (I), and each group in Formula (I) or its resonance structural formula is a carbon-carbon group
  • the compound obtained by rotating about the bond axis of a bond or a carbon-nitrogen single bond shall also be included.
  • R 1 to R 8 each independently represent a hydrogen atom, a hydroxy group, a C 1-20 alkyl group which may have a substituent, or a C 1-20 alkoxy group which may have a substituent.
  • R 9 to R 12 each independently represent a C 1-20 hydrocarbon group which may have a substituent
  • at least one of R 9 to R 12 is a C 1-20 aliphatic hydrocarbon group having a carboxy group as a substituent
  • at least one of R ⁇ 9> -R ⁇ 12> may be a C6-C20 aromatic hydrocarbon group which may have a substituent
  • the methylene group contained in the said aliphatic hydrocarbon group may be substituted by -O-.
  • the alkyl group having 1 to 20 carbon atoms represented by R 1 to R 8 may be linear, branched or cyclic. Specific examples of the linear or branched alkyl group include methyl, ethyl, propyl, isobutyl, butyl, tert-butyl, hexyl, heptyl, octyl, nonyl, decyl and heptadecyl groups. And undecyl group.
  • cyclic alkyl group examples include cyclopropyl group, 1-methylcyclopropyl group, cyclopentyl group, cyclohexyl group, 1,2-dimethylcyclohexyl group, cyclooctyl group, 2,4,6-trimethylcyclohexyl group, 4- Cyclohexyl cyclohexyl group etc. are mentioned.
  • Halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom;
  • a hydroxyl group; -NR a R b (R a and R b are Each independently represent a hydrogen atom or an alkyl group having 1 to 20 carbon atoms; a nitro group; a C1-10 alkoxy group such as a methoxy group and an ethoxy group; a C1-10 carbon atom such as a methoxycarbonyl group and an ethoxycarbonyl group Alkoxycarbonyl group; These etc. are mentioned.
  • C1-C20 alkoxy group represented by R ⁇ 1> -R ⁇ 8> group which -O- couple
  • a time period, 2-ethylhexyloxy group, etc. are mentioned.
  • Halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom
  • a hydroxyl group; -NR c R d (R c and R d are Each independently represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms; Nitro group; Alkoxy group having 1 to 10 carbon atoms such as methoxy group and ethoxy group; 1 to 10 carbon atoms such as methoxycarbonyl group and ethoxycarbonyl group Alkoxycarbonyl group; and the like.
  • R 1 ⁇ R 8 of, R 1 ⁇ R 4 is particularly preferably a hydrogen atom.
  • R ⁇ 5> -R ⁇ 8> is respectively independently a C1-C20 alkyl group which may have a hydrogen atom, a hydroxyl group, a substituent, or a C1-C20 alkoxy group which may have a substituent, and a hydrogen atom Or it is more preferable that it is a hydroxyl group.
  • R 1 to R 8 are each independently a hydroxyl group.
  • C1-C20 hydrocarbon group represented by R ⁇ 9> -R ⁇ 12> As a C1-C20 hydrocarbon group represented by R ⁇ 9> -R ⁇ 12> , a C1-C20 aliphatic hydrocarbon group, a C6-C20 aromatic hydrocarbon group, etc. are illustrated.
  • the aliphatic hydrocarbon group having 1 to 20 carbon atoms may be either saturated or unsaturated, and saturation is preferable.
  • the aliphatic hydrocarbon group having 1 to 20 carbon atoms may be any of linear, branched, and cyclic, preferably linear or branched.
  • linear or branched aliphatic hydrocarbon having 1 to 20 carbon atoms examples include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, vinyl group, 1-propenyl group and 2-propenyl group ( Linear aliphatic hydrocarbon groups such as allyl group), and branched aliphatic hydrocarbon groups such as isopropyl group, isobutyl group, isopentyl group, neopentyl group, and 2-ethylhexyl group. Carbon number of the said aliphatic hydrocarbon group becomes like this. Preferably it is 1-15, More preferably, it is 1-10.
  • the cyclic aliphatic hydrocarbon group may be monocyclic or polycyclic.
  • a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc. are mentioned.
  • Carbon number of the said cyclic aliphatic hydrocarbon group becomes like this. Preferably it is 3-8, More preferably, it is 3-6.
  • the methylene group contained in the C1-C20 aliphatic hydrocarbon group may be substituted with -O-.
  • group represented by a following formula is mentioned, for example.
  • * represents a bonding hand.
  • aromatic hydrocarbon group having 6 to 20 carbon atoms examples include phenyl group, xylyl group, trimethylphenyl group, dipropylphenyl group, di (2,2-dimethylpropyl) phenyl group and naphthyl group.
  • Carbon number of the said aromatic hydrocarbon group becomes like this.
  • it is 6-16, More preferably, it is 6-12, More preferably, it is 6-9.
  • the hydrocarbon group having 1 to 20 carbon atoms represented by R 9 to R 12 may have a substituent, and examples of the substituent include a carboxy group; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom; a methoxy group, an ethoxy group, and the like.
  • At least one of R ⁇ 9> -R ⁇ 12> is a C1-C20 aliphatic hydrocarbon group which has a carboxy group as a substituent.
  • the aliphatic hydrocarbon group having 1 to 20 carbon atoms having the carboxy group as a substituent preferably has 1 to 2, more preferably 1 carboxyl groups.
  • it is preferable that the said carboxy group is couple
  • group represented by a following formula is mentioned, for example. In the following formula, * represents a bonding hand.
  • At least one of R ⁇ 9> -R ⁇ 12> is a C6-C20 aromatic hydrocarbon group which may have a substituent.
  • the C6-C20 aromatic hydrocarbon group which may have the said substituent Preferably, they are a phenyl group, a xylyl group, a trimethylphenyl group, a dipropylphenyl group, a di (2, 2- dimethylpropyl) phenyl group, or; 2, 4- difluoro It is a phenyl group which has two halogen atoms as substituents, such as a phenyl group, a 2, 4- dichlorophenyl group, a 2, 4- dibromophenyl group, a 2, 4- diiodphenyl group, More preferably, a 2, 4- dimethylphenyl group, 2 And a 4,6-trimethylphenyl group or a 2,4-difluorophenyl group.
  • R ⁇ 9> and R ⁇ 12> is respectively independently a C1-C20 aliphatic hydrocarbon group which has a carboxy group as a substituent, and R ⁇ 10> and R ⁇ 11> respectively independently may have a substituent. It is preferable that it is a 6-20 aromatic hydrocarbon group.
  • ph1-ph10 represents a group represented by the following formula (* means a bond).
  • ca1-ca6 represent the group represented by a following formula (* means a bonding hand).
  • the compound represented by Formula (I) can be manufactured by making the compound represented by Formula (pt1), the compound represented by Formula (pt2), and the compound represented by Formula (pt3) react.
  • the total amount of the compound represented by the formula (pt1) and the compound represented by the formula (pt2) is preferably 1.5 to 2.5 mol relative to 1 mol of the compound represented by the formula (pt3).
  • the colored resin composition of this invention contains a coloring agent (A) and resin (B), and contains a compound in which a coloring agent (A) is represented by Formula (I).
  • the colored resin composition of this invention contains a polymeric compound (C) and a polymerization initiator (D) further.
  • the colored resin composition of this invention may contain the polymerization start adjuvant (D1), a solvent (E), and a leveling agent (F) further.
  • the colored resin composition of this invention contains compound (I) as a coloring agent (A). It is preferable that content of a compound (I) is 0.1-150 mass parts with respect to 100 mass parts of resin (B), It is more preferable that it is 0.5-100 mass parts, It is more preferable that it is 1-80 mass parts.
  • the content rate of a compound (I) is 50 mass% or more in the total amount of a coloring agent (A), It is more preferable that it is 80 mass% or more, It is further more preferable that it is 90 mass% or more.
  • the colored resin composition of this invention may contain dye (A1) and pigment (A2) other than a compound (I) as a coloring agent (A).
  • a dye (A1) is not specifically limited, A well-known dye can be used, For example, a solvent dye, an acid dye, direct dye, a mordant dye, etc. are mentioned. Examples of the dye include compounds classified as having a color other than pigments in the color index (Published by The Society of Dyers and Colourists), and known dyes described in dyeing notes (color dyeing yarn). .
  • azo dye cyanine dye, triphenylmethane dye, xanthene dye, phthalocyanine dye, anthraquinone dye, naphthoquinone dye, quinoneimine dye, methine dye, azomethine dye, squarylium dye (only And (I)), acridine dye, styryl dye, coumarin dye, quinoline dye, nitro dye, and the like.
  • an organic solvent soluble dye is preferable.
  • the pigment (A2) is not particularly limited, and known pigments can be used.
  • Examples of the pigment (A2) include pigments classified as pigments in the color index (Published by The Society of Dyers and Colourists).
  • pigment for example, CI pigment yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125 , Yellow pigments such as 128, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 194, 214;
  • Pigment oranges 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 and 38;
  • Green pigments such as pigment green 7, 36 and 58;
  • C.I. Brown pigments such as pigment brown 23 and 25;
  • the content rate of the coloring agent (A) is preferably 0.1 to 70% by mass, more preferably 0.5 to 60% by mass, still more preferably 1 to 50% by mass with respect to the total amount of solids in the colored resin composition.
  • total amount of solid content in this specification means the quantity remove
  • the total amount of solids and the content of each component thereof can be measured by known analysis means such as liquid chromatography or gas chromatography, for example.
  • resin (B) is not specifically limited, It is preferable that it is alkali-soluble resin, At least 1 sort (a) (Hereinafter, "(a)” may be chosen from the group which consists of unsaturated carboxylic acid and unsaturated carboxylic anhydride.
  • Resin which has a structural unit derived from the Resin (B) is a structural unit derived from the monomer (b) (Hereinafter, it may be called “(b)") which has a C2-C4 cyclic ether structure and ethylenically unsaturated bond, (a), and Structural unit derived from the copolymerizable monomer (c) (however, (a) and (b) is different) (hereinafter may be called “(c)”), and the structure which has ethylenically unsaturated bond in a side chain It is preferable to have at least 1 type of structural unit chosen from the group which consists of units.
  • (a) examples include acrylic acid, methacrylic acid, maleic anhydride, itaconic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, and succinic acid mono [2- (meth) acrylic acid. Royloxyethyl] etc., Preferably, they are acrylic acid, methacrylic acid, and maleic anhydride.
  • (b) is a monomer having a C2-C4 cyclic ether structure (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and a (meth) acryloyloxy group Is preferred.
  • a C2-C4 cyclic ether structure for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring
  • a (meth) acryloyloxy group Is preferred is preferred.
  • (meth) acrylic acid represents at least 1 sort (s) chosen from the group which consists of acrylic acid and methacrylic acid. Notation, such as “(meth) acryloyl” and “(meth) acrylate”, also has the same meaning.
  • glycidyl (meth) acrylate for example, glycidyl (meth) acrylate, vinyl benzyl glycidyl ether, 3, 4- epoxy cyclocyclo [5.2.1.0 2,6 ] decyl (meth) acrylate, 3-ethyl 3- (meth) acryloyloxymethyl oxetane, tetrahydrofurfuryl (meth) acrylate, etc. are mentioned,
  • glycidyl (meth) acrylate and 3 4- epoxy cyclocyclo [ 5.2.1.0 2,6 ] decyl (meth) acrylate and 3-ethyl-3- (meth) acryloyloxymethyl oxetane.
  • Resin which has a structural unit which has ethylenically unsaturated bond in a side chain adds (b) to the copolymer of (a) and (c), or (a) is added to the copolymer of (b) and (c). It can manufacture by making it.
  • the said resin may be able to add (a) to the copolymer of (b) and (c), and to make carbonic acid anhydride react further.
  • the weight average molecular weight of polystyrene conversion of resin (B) becomes like this.
  • it is 3,000-100,000, More preferably, it is 5,000-50,000, More preferably, it is 5,000-30,000.
  • the dispersion degree [weight average molecular weight (Mw) / number average molecular weight (Mn)] of resin (B) becomes like this.
  • Mw weight average molecular weight
  • Mn number average molecular weight
  • the acid value of resin (B) is 20-170 mg-KOH / g in conversion of solid content, Preferably it is 30-150 mg-KOH / g, More preferably, it is 40-135 mg-KOH / g.
  • the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be obtained by titration using, for example, an aqueous potassium hydroxide solution.
  • the content of resin (B) is preferably from 30 to 99.9 mass%, more preferably from 50 to 99.5 mass%, still more preferably from 70 to 99 mass%, based on the total amount of solids in the colored resin composition.
  • the content rate of resin (B) becomes like this.
  • it is 7-70 mass% with respect to the total amount of solid content of a colored resin composition. More preferably, it is 13-65 mass%, More preferably, it is 17-60 mass%.
  • a polymerizable compound (C) is a compound which can superpose
  • the compound etc. which have a polymerizable ethylenically unsaturated bond are mentioned, It is preferable.
  • a (meth) acrylic acid ester compound is preferable.
  • a polymeric compound (C) is a polymeric compound which has 3 or more of ethylenically unsaturated bonds.
  • a polymerizable compound trimethylol propane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, for example. And dipentaerythritol hexa (meth) acrylate.
  • the weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, more preferably 250 or more and 1,500 or less.
  • the content rate of a polymeric compound (C) is 7-65 mass% with respect to the total amount of solid content of a colored resin composition, More preferably, it is 13-60 mass% More preferably, it is 17-55 mass%.
  • the polymerization initiator (D) may be a compound capable of generating an active radical, an acid, or the like by the action of light or heat, and is not particularly limited as long as it is a compound capable of initiating polymerization, and a known polymerization initiator can be used.
  • produces an active radical it is N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulphate), for example.
  • content of a polymerization initiator (D) is 0.1-30 mass parts with respect to 100 mass parts of total amounts of resin (B) and a polymeric compound (C), More preferably, Preferably it is 1-20 mass parts.
  • content of a polymerization initiator (D) exists in said range, since it will become high sensitivity and the exposure time tends to be shortened, productivity of a color filter improves.
  • a polymerization start adjuvant (D1) is a compound or sensitizer used in order to accelerate superposition
  • polymerization start adjuvant As a polymerization start adjuvant (D1), 4,4'-bis (dimethylamino) benzophenone (common name mihiraz ketone), 4,4'-bis (diethylamino) benzophenone, 9,10- dimethoxy anthracene, 2, 4- diethyl thioxanthone, N-phenylglycine, etc. are mentioned.
  • these polymerization start adjuvant (D1) When using these polymerization start adjuvant (D1), its content becomes like this. Preferably it is 0.1-30 mass parts with respect to 100 mass parts of total amounts of resin (B) and a polymeric compound (C), More preferably, it is 1-20. It is a mass part. When the amount of the polymerization start aid (D1) is within this range, the coloring pattern can be formed with higher sensitivity, and the productivity of the color filter tends to improve.
  • Solvent (E) is not specifically limited, The solvent normally used in the field
  • an ester solvent a solvent containing -COO- in a molecule and not containing -O-
  • an ether solvent a solvent containing -O- in a molecule and not containing -COO-
  • an ether ester Solvents solvents containing -COO- and -O- in the molecule
  • ketone solvents solvents containing -CO- in the molecule and no -COO-
  • alcoholic solvents containing OH in the molecule,- Solvents not containing O-, -CO- and -COO-
  • aromatic hydrocarbon solvents amide solvents, dimethyl sulfoxide and the like.
  • Ester solvents such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetate and ⁇ -butyrolactone Solvents containing COO- and not containing -O-);
  • Ether solvents such as ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-1-butanol, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether (in a molecule, -O- And a solvent containing no -COO-);
  • 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 Solvent containing -COO- and -O-);
  • Ketone solvents such as 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), heptanone, 4-methyl-2-pentanone, and cyclohexanone (containing -CO- in the molecule, -COO Solvents that do not contain-);
  • Alcohol solvents such as butanol, cyclohexanol, and propylene glycol (solvents containing OH in the molecule and not containing -O-, -CO-, and -COO-);
  • Amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone;
  • propylene glycol monomethyl ether acetate propylene glycol monomethyl ether
  • 4-hydroxy-4-methyl-2-pentanone diacetone alcohol
  • ethyl lactate ethyl 3-ethoxypropionate
  • the content rate of a solvent (E) becomes like this.
  • it is 60-95 mass% with respect to the total amount of the colored resin composition of this invention, More preferably, it is 65-92 mass%. In other words, the total amount of solid content of a colored resin composition becomes like this.
  • it is 5-40 mass%, More preferably, it is 8-35 mass%.
  • leveling agent (F) examples include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants having fluorine atoms. These may have a polymeric group in a side chain.
  • silicone type surfactant As silicone type surfactant, surfactant etc. which have a siloxane bond in a molecule
  • numerator are mentioned.
  • fluorine-type surfactant surfactant etc. which have a fluorocarbon chain
  • silicone type surfactant which has the said fluorine atom, surfactant etc. which have a siloxane bond and a fluorocarbon chain
  • Specific examples thereof include Mega Pack (R) R08, BL20, F475, F477, F443 (manufactured by DIC Corporation), and the like.
  • content of a leveling agent (F) becomes like this.
  • a leveling agent (F) is 0.001-0.2 mass% with respect to the total amount of a colored resin composition, More preferably, it is 0.002-0.1 mass%.
  • content of a pigment dispersant is not contained in this content. If content of a leveling agent (F) exists in said range, flatness of a color filter can be made favorable.
  • the colored resin composition of this invention may also contain the additive known in the said technical field, such as a filler, another high molecular compound, an adhesion promoter, antioxidant, an optical stabilizer, a chain transfer agent, as needed.
  • a filler such as a filler, another high molecular compound, an adhesion promoter, antioxidant, an optical stabilizer, a chain transfer agent, as needed.
  • the coloring resin composition of this invention is a coloring compound (A) and resin (B), and a polymeric compound (C), a polymerization initiator (D), a polymerization start adjuvant (D1), a solvent (E), and leveling which are used as needed. It can prepare by mixing agent (F) and other components.
  • the photolithographic method As a method of manufacturing a coloring pattern with the colored resin composition of this invention, the photolithographic method, the inkjet method, the printing method, etc. are mentioned. Especially, the photolithographic method is preferable.
  • a colored resin composition contains the compound represented by Formula (I), especially the color filter excellent in heat resistance can be produced.
  • the said color filter is useful as a color filter used for a display apparatus (for example, a liquid crystal display device, an organic electroluminescent apparatus, an electronic paper, etc.) and a solid-state image sensor.
  • the crude product A89 part was dissolved in 370 parts of methanol (Kanto Chemical Co., Ltd.), and after cooling to 0 degreeC, 51 parts of thionyl chloride (made by Tokyo Chemical Industry Co., Ltd.) were added. It stirred at 23 degreeC for 16 hours, the water was added after completion
  • Identification of the compound represented by formula (1-18) was carried out by converting the compound represented by formula (1-18-1) which is a t-Bu ester.
  • the measurement of the weight average molecular weight (Mw) and number average molecular weight (Mn) of polystyrene conversion of resin was performed on condition of the following by GPC method.
  • HLC-8120 GPC manufactured by Tosoh Corporation
  • Test liquid solid content concentration 0.001-0.01 mass%
  • the ratio (Mw / Mn) of the weight average molecular weight and number average molecular weight of polystyrene conversion obtained above was made into dispersion degree.
  • each component represents the following compounds.
  • Colorant (A-1) Compound represented by formula (1-6)
  • Colorant (A-2) Compound represented by formula (1-13)
  • Colorant (A-3) Compound represented by formula (1-20)
  • Colorant (A-x) Compound represented by formula (x)
  • Resin (B-1) Resin (B-1) (solid content conversion)
  • Leveling agent (F-1): Polyether modified silicone oil (Toray Silicone SH8400 made by Toray Dow Corning Co., Ltd.)
  • the chromaticity of a colored coating film is the xy chromaticity coordinate (x, y in the XYZ table color system of CIE from the spectrometer measured using the colorimeter (OSP-SP-200; product made by Olympus Co., Ltd.), and the characteristic function of C light source. ) And the stimulus value Y.
  • the obtained colored coating film was heated at 230 degreeC in oven for 2 hours.
  • An ultraviolet-ray cut filter (COLORED OPTICAL GLASS L38; product made by Hoya Corporation; cuts light of 380 nm or less) is arrange
  • each component represents the following compounds.
  • the color filter excellent in heat resistance can be formed.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Nonlinear Science (AREA)
  • Structural Engineering (AREA)
  • Architecture (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Mathematical Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)

Abstract

La présente invention concerne un composé qui est représenté par la formule chimique (I) et qui est capable de former un filtre coloré ayant une excellente résistance thermique; une composition de résine colorée; un filtre coloré; et un dispositif d'affichage.
PCT/KR2019/002981 2018-03-16 2019-03-14 Composé, composition de résine colorée, filtre coloré et dispositif d'affichage WO2019177401A1 (fr)

Priority Applications (2)

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KR1020207020600A KR20200122300A (ko) 2018-03-16 2019-03-14 화합물, 착색 수지 조성물, 컬러 필터 및 표시 장치
CN201980019574.4A CN111886296B (zh) 2018-03-16 2019-03-14 化合物、着色树脂组合物、滤色器及显示装置

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JP2018240241A JP7101111B2 (ja) 2018-03-16 2018-12-21 化合物
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023282014A1 (fr) * 2021-07-05 2023-01-12 富士フイルム株式会社 Composé, pigment, feuille d'encre pour impression par transfert thermosensible

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JP2009036811A (ja) * 2007-07-31 2009-02-19 Konica Minolta Business Technologies Inc 電子写真用トナー及び画像形成方法
JP2009180875A (ja) * 2008-01-30 2009-08-13 Konica Minolta Business Technologies Inc 電子写真用カラートナー
US20100266507A1 (en) * 2007-01-30 2010-10-21 Terpetschnig Ewald A Luminescent compounds
WO2015147312A1 (fr) * 2014-03-26 2015-10-01 住友化学株式会社 Dispositif d'affichage à cristaux liquides
KR20180026967A (ko) * 2016-09-05 2018-03-14 삼성에스디아이 주식회사 신규한 화합물, 코어-쉘 염료, 이를 포함하는 감광성 수지 조성물 및 컬러필터

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Publication number Priority date Publication date Assignee Title
US20100266507A1 (en) * 2007-01-30 2010-10-21 Terpetschnig Ewald A Luminescent compounds
JP2009036811A (ja) * 2007-07-31 2009-02-19 Konica Minolta Business Technologies Inc 電子写真用トナー及び画像形成方法
JP2009180875A (ja) * 2008-01-30 2009-08-13 Konica Minolta Business Technologies Inc 電子写真用カラートナー
WO2015147312A1 (fr) * 2014-03-26 2015-10-01 住友化学株式会社 Dispositif d'affichage à cristaux liquides
KR20180026967A (ko) * 2016-09-05 2018-03-14 삼성에스디아이 주식회사 신규한 화합물, 코어-쉘 염료, 이를 포함하는 감광성 수지 조성물 및 컬러필터

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023282014A1 (fr) * 2021-07-05 2023-01-12 富士フイルム株式会社 Composé, pigment, feuille d'encre pour impression par transfert thermosensible

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