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WO2019107687A1 - Composition de colorants, dispersion de colorants, composition de résine photosensible, filtre coloré et afficheur à cristaux liquides - Google Patents

Composition de colorants, dispersion de colorants, composition de résine photosensible, filtre coloré et afficheur à cristaux liquides Download PDF

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Publication number
WO2019107687A1
WO2019107687A1 PCT/KR2018/007001 KR2018007001W WO2019107687A1 WO 2019107687 A1 WO2019107687 A1 WO 2019107687A1 KR 2018007001 W KR2018007001 W KR 2018007001W WO 2019107687 A1 WO2019107687 A1 WO 2019107687A1
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Prior art keywords
group
substituted
unsubstituted
colorant
same
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PCT/KR2018/007001
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English (en)
Korean (ko)
Inventor
이다미
김재준
박상균
박종호
양승진
이수연
이재용
정지혜
최상아
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LG Chem Ltd
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LG Chem Ltd
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Priority to JP2019502070A priority Critical patent/JP6687189B2/ja
Priority to CN201880003035.7A priority patent/CN110099966B/zh
Publication of WO2019107687A1 publication Critical patent/WO2019107687A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/008—Preparations of disperse dyes or solvent 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/28—Pyronines ; Xanthon, thioxanthon, selenoxanthan, telluroxanthon dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
    • C09B67/0084—Dispersions of dyes
    • 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
    • G03F7/004—Photosensitive materials
    • 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
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/542—Dye sensitized solar cells

Definitions

  • the present invention relates to a colorant composition, a colorant dispersion, a photosensitive resin composition, a color filter, and a liquid crystal display device.
  • LEDs or OLED devices which do not drive liquid crystal but perform self-luminescence instead of conventional CCFL have been widely used as a light source of a liquid crystal display (LCD).
  • LCD liquid crystal display
  • a pigment dispersion method using a pigment as a colorant is generally applied to realize a color filter.
  • the pigment is present in the form of particles to scatter light, and the surface area of the pigment is rapidly increased due to the fineness of the pigment, and the dispersion stability is deteriorated due to the uneven pigment particle. Therefore, in order to achieve the high brightness, high contrast ratio, and high resolution required recently, it has been investigated to use a dye as a coloring agent instead of a pigment.
  • the dye since the dye has a low solubility, the dye is not well dispersed and the brightness of the color filter can not be sufficiently satisfied.
  • the present invention provides a colorant composition capable of providing a colorant dispersion having excellent dispersibility, a colorant dispersion prepared using the same, and a photosensitive resin composition.
  • the present invention also provides a color filter manufactured using the above-mentioned photosensitive resin composition and a liquid crystal display device including the same.
  • a second xanthene dye having a number of negative charges larger than that of positive charges by at least 1, and an ionic binder having an amine value of 0 to 200 mgKOH / g and a dispersant comprising an ammonium structure
  • Another embodiment of the present invention is a composition comprising the colorant composition; Dispersing agent; Binder resin; And a colorant dispersion comprising a solvent.
  • Another embodiment of the present invention provides a photosensitive resin composition
  • a photosensitive resin composition comprising the colorant dispersion, a binder resin, a polyfunctional monomer, and a photopolymerization initiator.
  • Another embodiment of the present invention provides a color filter comprising a transparent substrate and a colored layer provided on the transparent substrate, wherein the colored layer comprises a cured product of the photosensitive resin composition.
  • Another embodiment of the present invention provides a liquid crystal display device including the color filter.
  • the colorant composition and colorant dispersion according to some embodiments of the present invention are used, they are excellent in storage stability, transparency and heat resistance, and are excellent in use for color filter applications.
  • One embodiment of the present invention is a dye sensitized solar cell comprising: a first xanthene dye having the same number of positive and negative charges; And a second xanthene dye having a number of negative charges larger than the number of positive charges by 1 or more and an amine value of 0 to 200 mgKOH / g, wherein the dispersant comprising an ammonium structure is ion-bonded.
  • both the first xanthene dye and the second xanthene dye have a similar structure as a xanthene dye.
  • the first xanthene dye has the same number of positive charges and negative charges, while the second xanthene dye has a number of negative charges larger than that of positive charges by one or more.
  • the dispersion stability may be deteriorated due to the re-aggregation of the particles due to the pi-pi interactions of the xanthene dyes.
  • the first xanthene-based dye and the second xanthene-based dye having the above-mentioned characteristics are included so that some or all of the second xanthene-based dyes are adjacent to each other or two or more of the first xanthene- Lt; / RTI > dye or between the dyes or the end of the first xanthene dye.
  • the first xanthene dyes exhibit color as a xanthene dye
  • the second xanthene dyes exhibit color and serve to disperse the first xanthene dyes, thereby enhancing dispersion stability have.
  • the dispersant contains an ammonium structure, the dispersant has a cationic property, whereby the negative charge of the second xanthene dye can ionically bond with a dispersant to form a complex. Due to the presence of such a second xanthene dye, the dispersion stability can be greatly improved. Thus, it is possible to provide a colorant dispersion which can prevent re-aggregation of the first xanthene-based dye, has small dispersed particles, good brightness and excellent dispersion stability.
  • the first xanthene dye has a maximum absorption wavelength between 500 and 580 nm, and the maximum absorption wavelength of the first xanthene dye and the maximum absorption of the second xanthene dye The difference in wavelength is less than 100 nm.
  • the first xanthene dye has a maximum absorption wavelength between 500 and 580 nm, and the maximum absorption wavelength of the first xanthene dye and the maximum absorption of the second xanthene dye
  • the wavelength difference is more than 0 and 100 nm or less. More preferably in the range of more than 0 and 50 nm or less, and most preferably in the range of more than 0 and 20 nm or less.
  • the first xanthene-based dye can be described as a first dye
  • the second xanthene-based dye can be described as a second dye, respectively.
  • the amine value of the dispersant containing the ammonium structure is 0 to 200 mg KOH / g.
  • the amine value can be from 0 to 100 mg KOH / g, and from 0 to 100 mg KOH / g.
  • the amine value of the dispersant comprising the ammonium structure may be greater than 0 to 160 mg KOH / g.
  • the first xanthene dye is represented by the following formula (1) and includes the same number of positive and negative dyes
  • the second xanthene dye is represented by the following formula And includes a dye having a number of negative charges larger than that of positive charges by one or more.
  • R 1 to R 4 are the same or different and are each independently hydrogen; heavy hydrogen; Anionic group; A hydroxy group; A sulfonamide group; Sulfonic acid base; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; And a dianhydride comprising a nitrogen atom,
  • R 5 to R 9 are the same or different and each independently hydrogen; heavy hydrogen; Anionic group; A hydroxy group; A sulfonamide group; Sulfonic acid base; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heteroaryl group, provided that at least one of R 5 to R 9 is an anionic group; Sulfonic acid base; Or a sulfonamide group,
  • R 10 and R 11 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitro group; Or a substituted or unsubstituted alkyl group, r 10 and r 11 are integers of 0 to 3, and when r 10 and r 11 are each 2 or more, the structures in parentheses are the same or different from each other.
  • R 21 to R 24 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Anionic group; A hydroxy group; A sulfonamide group; Sulfonic acid base; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted heteroaryl group; And a dianhydride including a nitrogen atom, and at least one of R 21 to R 24 is an alkyl group substituted or unsubstituted with an anionic group, a sulfonic acid group, or a sulfonamide group; An aryl group substituted with an anionic group, a sulfonic acid group, or a sulfonamide group; Or a heteroaryl group substituted by an anionic group, a sulfonic acid group, or a sulfonamide group,
  • R 25 to R 29 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Anionic group; A hydroxy group; A sulfonamide group; Sulfonic acid base; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group; And substituted or unsubstituted heteroaryl groups, provided that at least one of R 25 to R 29 is an anionic group; Sulfonic acid base; Or a sulfonamide group,
  • R 30 and R 31 are the same or different and each independently hydrogen; heavy hydrogen; A halogen group; A nitro group; Or a substituted or unsubstituted alkyl group, r 30 and r 31 are integers of 0 to 3, and when r 30 and r 31 are each 2 or more, the structures in parentheses are the same or different from each other.
  • R 1 to R 4 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; And a dianhydride comprising a nitrogen atom, wherein R 21 to R 24 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; And a dianhydride comprising a nitrogen atom, with the remaining substituents being as defined above.
  • R 1 to R 4 are the same or different and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a dianhydride group containing a nitrogen atom.
  • R 1 to R 4 are the same or different and each independently hydrogen; An aryl group substituted with an anionic group or an alkyl group; Or an alkyl group substituted or unsubstituted with an imino group containing a nitrogen atom.
  • R 1 to R 4 are the same or different and each independently hydrogen; A phenyl group substituted with a methyl group; A phenyl group substituted by at least one member selected from the group consisting of a methyl group and an anionic group; An ethyl group; Propyl group; Or a propyl group substituted with an imino group containing a nitrogen atom.
  • R 5 to R 9 are the same or different and each independently hydrogen; Or an anionic group.
  • R 5 to R 9 are the same or different and each independently hydrogen; Or SO 3 - .
  • R 10 and R 11 are the same or different and each independently hydrogen; Or a deuterium, r 10 and r 11 is an integer from 0 to 3, when the r 10 and r 11 each 2 or more, the structure in the parentheses is the same as or different from each other.
  • R 21 to R 24 are the same or different and each independently represents a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a dianhydride group containing a nitrogen atom.
  • R 21 to R 24 are the same or different and each is an alkyl group substituted or unsubstituted with an anhydride group containing a nitrogen atom; Or an aryl group substituted by at least one selected from the group consisting of an anionic group and an alkyl group.
  • R 21 to R 24 are the same or different from each other, and each independently represents an ethyl group; Propyl group; A propyl group substituted with an imino group containing a nitrogen atom; A phenyl group substituted with a methyl group; Or a phenyl group substituted by at least one selected from the group consisting of a methyl group and an anionic group.
  • substituted or unsubstituted A halogen group; An alkyl group; An alkenyl group; An alkoxy group; A cycloalkyl group; An arylalkenyl group; An aryl group; An aryloxy group; Arylalkyl groups; An arylalkenyl group; An alkylamine group; An aralkylamine group; An arylamine group; A heteroaryl group; A hydroxy group; Cyano; A heterocyclic group containing at least one of N, O, S or P atoms; A dianhydride containing a nitrogen atom; Sulfonic acid base; Substituted with at least one substituent selected from the group consisting of a sulfonamido group and an anionic group, or has no substituent group.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl and heptyl.
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples thereof include, but are not limited to, an alkenyl group substituted with an aryl group such as a stilbenyl group or a styrenyl group.
  • the alkoxy group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • the alkenyloxy group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 20 carbon atoms, and particularly preferably a cyclopentyl group and a cyclohexyl group.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the arylalkyl group is specifically an aryl moiety having 6 to 30 carbon atoms and an alkyl moiety having 1 to 30 carbon atoms.
  • Specific examples include benzyl, p-methylbenzyl, m-methylbenzyl, p-ethylbenzyl, m-ethylbenzyl, 3,5-dimethylbenzyl, Group, an?,?
  • -benzyloxybenzyl group naphthylmethyl group, naphthylethyl group, naphthylisopropyl group, pyrrolylmethyl group, but are not limited to, an ethyl group, an aminobenzyl group, a nitrobenzyl group, a cyanobenzyl group, a 1-hydroxy-2-phenylisopropyl group, a 1-chloro-2-phenylisopropyl group and the like.
  • the aryl moiety of the arylalkenyl group may be an explanation of the aryl moiety described below, and the alkenyl moiety may be an explanation of the alkenyl moiety mentioned above.
  • the aryl group may be a monocyclic aryl group or a polycyclic aryl group.
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms.
  • Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. And preferably 10 to 30 carbon atoms.
  • Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a klycenyl group and a fluorenyl group.
  • the fluorenyl group may have a substituent, and the substituents may combine to form a spiro structure.
  • the heterocyclic group is a heterocyclic group and is a heterocyclic group containing O, N or S, and the number of carbon atoms is not particularly limited, but preferably 2 to 30 carbon atoms.
  • the heterocyclic group include a thiophene group, a furane group, a furyl group, an imidazole group, a thiazole group, an oxazole group, an oxadiazole group, a triazole group, a pyridyl group, a bipyridyl group, a triazine group, , A quinolinyl group, an isoquinoline group, an indole group, a carbazole group, a benzoxazole group, a benzoimidazole group, a benzothiazole group, a benzocarbazole group, a benzothiophene group, a dibenzothiophene group, a benzofuranyl group, And the
  • the number of carbon atoms of the dianhydride group containing a nitrogen atom is not particularly limited, but is preferably 4 to 20.
  • isoindoline-1,3-dione isoindoline-1,3-dione.
  • the alkylene group means that there are two bonding sites in the alkane.
  • the alkylene group may be linear, branched or cyclic.
  • the number of carbon atoms of the alkylene group is not particularly limited, but is, for example, 1 to 30 carbon atoms.
  • the sulfonic acid group may be represented as -SO 3 X 'and X' may be hydrogen or a Group 1 element.
  • the sulfonic acid base is -SO 3 Na.
  • the sulfonamide group may be expressed as: -SO 2 NRxRy, for example, Rx and Ry are the same as or different from each other, each independently represent a substituted or unsubstituted carbon atoms of 1 to 30 linear or branched alkyl group ; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • the anionic group has a chemical bond with the structure of the formula (1), and the anionic group is not particularly limited and includes, for example, those described in U.S. Patent No. 7,939,644, Japanese Patent Publication No. 2006-003080, Japanese Patent Publication No. 2006-001917, Japanese Unexamined Patent Publication No. 2005-159926, Japanese Unexamined Patent Application No. 2007-7028897, Japanese Unexamined Patent Application No. 2005-071680, Korean Unexamined Patent Publication No. 2007-7000693, Japanese Unexamined Patent Publication No. 2005-111696, Japanese Unexamined Patent Publication No.
  • the anions described in Specification < RTI ID 0.0 > 2014-199436 < / RTI >
  • Specific examples of the anionic group include a trifluoromethanesulfonic acid anion, a bis (trifluoromethylsulfonyl) amide anion, a bistrifluoromethanesulfonimide anion, a bisperfluoroethylsulfonimide anion, a tetraphenylborate anion, SO 3 - , CO 2 - , SO 2 N - SO 2 CF 3 , SO 2 N (tetrafluoroborate), tetrakis (pentafluorophenyl) borate, - SO 2 CF 2 CF 3, but include a halogen group such as fluorine group, an iodo group, a chlorine group, it is not limited thereto.
  • the anionic group may have an anion per se, or may exist in the form of a complex with other cations.
  • the total charge of the compound molecules of the present invention may vary. Since the amine group of the compound of the present invention has a cation, the sum of the total charges of the molecule may have an anion value of 0 minus one in the number of substituted anionic groups.
  • the monomer is a repeating unit constituting the polymer, and the monomer can be contained in the main chain in the polymer to form a polymer.
  • unit means a repeating structure in which a monomer is contained in a polymer, and a monomer is bonded to the polymer by a polymer.
  • the first xanthene dye is represented by the following general formula (3) and includes the same number of positive and negative dyes
  • the second xanthene dye is represented by the following general formula And includes a dye having a number of negative charges larger than that of positive charges by one or more.
  • R 12 , R 13 , R 32 and R 33 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitro group; A substituted or unsubstituted alkyl group; Anionic group; Sulfonic acid base; Or a sulfonamide group and, r 12 and r 13 is an integer of 0 to 5, r 32 is an integer from 0 to 5, r 33 is an integer from 0 to 4, r 12, r 13, r 32 and r 33 Are two or more, the structures in parentheses are the same or different from each other,
  • R 61 and R 62 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a dianhydride comprising a nitrogen atom,
  • X is an anionic group; Sulfonic acid base; Or a sulfonamide group,
  • R 61 and R 62 may be hydrogen.
  • the colorant composition may further include a dye of Formula 4-1 below.
  • R 50 to R 53 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A nitro group; Or a substituted or unsubstituted alkyl group, r 50 and r 51 are integers of 0 to 4, r 52 and r 53 are integers of 0 to 3, and r 50 to r 53 are each 2 or more, the structure in parentheses is Are the same or different,
  • Xa and Xb are the same or different from each other and each independently an anionic group; Sulfonic acid base; Or a sulfonamide group,
  • R 45 to R 49 are the same or different from each other, and each independently hydrogen; heavy hydrogen; Anionic group; A hydroxy group; A sulfonamide group; Sulfonic acid base; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group; And substituted or unsubstituted heteroaryl groups, provided that at least one of R 45 to R 59 is an anionic group; Sulfonic acid base; Or a sulfonamide group.
  • the first xanthene dye is represented by the following formula (5) and includes the same number of positive and negative dyes
  • the second xanthene dye is represented by the following formula And includes a dye having a number of negative charges larger than that of positive charges by one or more.
  • R 14 to R 17 , and R 34 to R 37 are the same or different and are each independently a substituted or unsubstituted alkyl group
  • R 61 and R 62 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; Or a dianhydride comprising a nitrogen atom,
  • X1 to X3 are the same or different and each independently an anionic group; Sulfonic acid base; Or a sulfonamide group.
  • R 14 to R 17 , and R 34 to R 37 may be methyl groups.
  • R 61 and R 62 may be hydrogen.
  • the colorant composition may further include a dye of Formula 6-1 below.
  • R 38 to R 41 are the same or different and are each independently a substituted or unsubstituted alkyl group
  • X4 to X6 are the same or different from each other and each independently an anionic group; Sulfonic acid base; Or a sulfonamide group.
  • the first xanthene dye may be any of the following structures.
  • the second xanthene dye may be any of the following structures.
  • the dispersant may include 3 to 50 mol%, preferably 4 to 40 mol%, based on 100 mol% of the total monomer units of the monomer unit containing the ammonium structure.
  • the second xanthene dye may further include a counter cation.
  • the colorant composition according to one embodiment of the present invention may further include counter cations in a number corresponding to the number of negative charges in the second xanthene-based dye than in the positive charge.
  • the counter cation may be a hydrogen ion, a sodium ion or a cationic group, and these may include, for example, 1 to 7 per molecule of the second xanthene dye.
  • the dispersant may further include a counter anion.
  • Counter anion may be an anion of an inorganic or organic, in particular Cl - may be a halogen, such as a date.
  • the dispersant may include counter anions in a number corresponding to the positive charge number of the dispersant.
  • the colorant composition according to one embodiment of the present invention can be cleaned as described below wherein the counter cation or counter anion is removed and the cationic structure contained in the dispersant is counter cationic of the second xanthene dye can do.
  • the dispersant is represented by the following general formula (7).
  • Ra to Rd are the same or different from each other and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; A substituted or unsubstituted arylalkyl group; -L-NHCO-R; Or -L-OCO-R, or two of Ra to Rd may be bonded to each other to form a substituted or unsubstituted ring,
  • R is hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted arylalkyl group,
  • L is a substituted or unsubstituted alkylene group.
  • At least one of Ra to Rd, and more preferably at least 2 include a long chain having at least 5 carbon atoms.
  • dispersion stability by the dispersing agent can be further increased.
  • the dispersant comprises a unit represented by the following general formula (8).
  • Rb to Rd are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted arylalkyl group, or two of Rb to Rd are bonded to each other to form a substituted or unsubstituted ring,
  • Z is an alkylene group; An arylene group; -L-NHCO-; Or -L-OCO-, L is an alkylene group,
  • Re to Rg are the same or different from each other and each independently represents hydrogen; Or an alkyl group.
  • the dispersant has a weight average molecular weight of 1,000 to 10,000. Preferably 3,000 to 8,000, and more preferably 5,000 to 7,000.
  • the end of the dispersant is hydrogen, a halogen group or an alkyl group.
  • the dispersant further includes at least one unit selected from the following formulas (9) to (12) in addition to the unit represented by the formula (8).
  • R 1, R 2, R 3, R 4, R 5 and R 6 are the same or different and each independently represents hydrogen or an alkyl group having 1 to 20 carbon atoms,
  • Rk and Rs are the same or different and each independently represents an alkyl group having 1 to 20 carbon atoms
  • Ro is an arylalkyl group having 7 to 20 carbon atoms
  • Rw and Rx are the same or different and each independently represents hydrogen, an alkyl group having 1 to 20 carbon atoms or an arylalkyl group having 7 to 20 carbon atoms,
  • L 1 and L 2 are the same or different and each independently represents an alkylene group having 1 to 6 carbon atoms; and m is an integer of 1 to 6.
  • the dispersant may comprise the following units, the rightmost unit of which is essential.
  • the colorant composition further comprises a solvent.
  • the solvent is selected from the group consisting of acetone, methyl ethyl ketone, methyl isobutyl ketone, methyl cellosolve, ethyl cellosolve, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether , Propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, chloroform, methylene chloride, 1,2-dichloroethane, 1,1,1-trichloroethane, 1 Cyclohexane, benzene, toluene, xylene, methanol, ethanol, isopropanol, propanol, butanol, t-butanol, 2-ethylhexanoate, 2-trichloroe
  • the colorant composition may further comprise a salt.
  • This salt can serve to refine the dispersed particles in a finishing step described later.
  • the salt can be removed by washing with a solvent such as distilled water, and is not particularly limited as long as it is a component capable of helping micronization.
  • a material such as NaCl may be used.
  • a salt When a salt is used, its amount to be used may be determined as necessary, and may be used, for example, about 2 to 8 times, preferably about 3 to 5 times, based on the total weight of the first and second xanthene dyes .
  • the salt may be removed by washing as described above, in which case the solvent may also be removed. The washing may be carried out once or twice or more times as necessary.
  • the second xanthene dye may be contained in an amount of 3 to 30 parts by weight, preferably 5 to 50 parts by weight, based on 100 parts by weight of the first xanthene dye.
  • the dispersant may be contained in an amount of from 1.5 to 8 times, preferably from 2 to 6 times the weight of the second xanthene dye.
  • the solvent may be contained at a weight of 1/15 to 1/5 of the weight of the solid.
  • the solid weight means the weight of the solid content including the contents of the first and second xanthene dyes and, if used, salt.
  • the above-described colorant composition may further comprise at least one of a dye and a pigment.
  • the colorant composition may further comprise a phthalocyanine pigment, for example, PB15: 6.
  • Another embodiment of the present invention is a colorant composition as described above; Dispersing agent; Binder resin; And a colorant dispersion comprising a solvent.
  • the colorant dispersions herein may be replaced by the term millbase.
  • the colorant composition contained in the colorant dispersion means a state in which the solvent is removed. If a salt is used in the colorant composition, it is removed by washing with a salinity solvent and then incorporated into the colorant dispersion.
  • the colorant dispersion may further comprise beads.
  • the beads having a particle size of 0.05 to 1.5 mm can be used.
  • beads having particle diameters of 0.1 mm, 0.3 mm, 0.5 mm, 0.8 mm, and / or 1 mm can be used.
  • the material of the beads at least one of aluminum oxide, aluminum silicate, zirconium oxide, and / or silicon nitride may be used.
  • the amount of beads to be used is not particularly limited, but may be 10 to 40 times the total weight of the complexing agent composition and the dispersing agent. Such beads may serve to disperse the constituents of the compositions contained in the colorant dispersion.
  • the colorant dispersion described above may further comprise at least one of a dye and a pigment.
  • a dye and a pigment examples of further included dyes and pigments are the same as those exemplified for the dyes and pigments further included in the colorant composition described above.
  • the colorant composition may be subjected to a micronization process before being incorporated into the colorant dispersion.
  • the micronization process refers to a process in which a physical force is applied to micronize.
  • the diameter of the dispersed particles in the colorant composition by the micronization process is 40 nm to 100 nm.
  • the diameter means the maximum length of dispersed particles.
  • the diameter of the particles after micronization can be measured by SEM or TEM equipment.
  • a specific example using the SEM measurement method is as follows. First, 0.01 g of the colorant dispersion containing micronized particles is added to a chloroform solvent, and treated with medium intensity for 10 minutes by using an ultrasonic equipment JAC-5020 manufactured by KODO Corporation, thereby dropping the particles and the particles well. Then drop a drop on the glass and heat it on a 50 degree hot plate for 5 minutes to remove the solvent. The particles are coated with a Pt layer having a thickness of about 100 to 200 ⁇ , and the particle diameter is observed with an SEM.
  • PGEMA propylene glycol monomethyl ether acetate
  • the diameter of the dispersed particles in the colorant dispersion is more than 100 nm, there arises a problem that the contrast ratio is reduced due to scattering of light, and when the dispersed particle size is too small, the contrast ratio is reduced by re- And the dispersion (Millbase), the range of 40 to 100 nm, more preferably 40 to 80 nm, is suitable.
  • the dispersed particle size of the colorant composition is 40 nm to 80 nm and the viscosity is 2.5 to 6.5 cP.
  • the binder resin is not particularly limited as long as it can exhibit physical properties such as strength and developability of a film made of a resin composition.
  • the binder resin may be a copolymer resin of a monomer having a multifunctional monomer that imparts mechanical strength and a monomer that imparts alkali solubility.
  • the binder resin may further include a binder generally used in the art.
  • the multifunctional monomer which imparts the mechanical strength of the film is an unsaturated carboxylic acid ester; Aromatic vinyls; Unsaturated ethers; Unsaturated imides; And acid anhydrides.
  • unsaturated carboxylic acid esters include benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, isobutyl (Meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl Hydroxypropyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (Meth) acrylate, 3-methoxybutyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, CDI ethylene glycol (Meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytri
  • aromatic vinyl monomers include aromatic vinyl monomers such as styrene,? -Methylstyrene, (o, m, p) -vinyltoluene, (o, Styrene, but are not limited thereto.
  • unsaturated ethers include, but are not limited to, vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether.
  • unsaturated imide are selected from the group consisting of N-phenylmaleimide, N- (4-chlorophenyl) maleimide, N- (4-hydroxyphenyl) maleimide and N-cyclohexylmaleimide But is not limited to these.
  • Examples of the acid anhydride include maleic anhydride, methylmaleic anhydride, and tetrahydrophthalic anhydride, but are not limited thereto.
  • the alkali-solubilizing monomer is not particularly limited as long as it contains an acid group, and examples thereof include (meth) acrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, monomethyl maleic acid, 5-norbornene- (Meth) acryloyloxy) ethyl phthalate, mono-2 - ((meth) acryloyloxy) ethyl succinate, omega -carboxypolycaprolactone mono But it is not limited to these.
  • the acid value of the binder resin is 50 to 130 KOH mg / g and the weight average molecular weight is 1,000 to 50,000.
  • the content of the colorant composition comprising the complex of the first xanthene dye and the second xanthene dye and the dispersant in the colorant dispersion may be 5 to 20 wt%.
  • the binder resin in the colorant dispersion may be 1 to 60% by weight, the dispersant may be 1 to 40% by weight, and the solvent may be 10 to 80% by weight.
  • An embodiment of the present invention provides a photosensitive resin composition
  • a photosensitive resin composition comprising the above-described colorant dispersion, a binder resin, a polyfunctional monomer and a photopolymerization initiator.
  • binder resin and the solvent those described in connection with the above-described colorant dispersion and colorant composition may be used.
  • the multifunctional monomer is a monomer that functions to form a photoresist phase by light.
  • Specific examples thereof include propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol di Acrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate, tetraethylene glycol methacrylate, bisphenoxy ethyl alcohol diacrylate, trishydroxy ethylisocyanurate trimethacrylate, trimethyl 1, 2 or 3 groups selected from the group consisting of propane trimethacrylate, diphenyl pentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexa methacrylate.
  • the photopolymerization initiator is not particularly limited as long as it is an initiator that generates radicals by light to induce crosslinking.
  • Examples of the photopolymerization initiator include a group consisting of an acetophenone compound, a nonimidazole compound, a triazine compound, and a oxime compound It may be at least one selected.
  • the acetophenone compound may be at least one selected from the group consisting of 2-hydroxy-2-methyl-1-phenylpropan-1-one, 1- (4-isopropylphenyl) (2-hydroxyethoxy) -phenyl- (2-hydroxy-2-propyl) ketone, 1-hydroxycyclohexyl phenyl ketone, benzoin methyl ether, benzoin ethyl ether, benzoin isobutyl ether, Butyl ether, 2,2-dimethoxy-2-phenylacetophenone, 2-methyl- (4-methylthio) phenyl- (4-morpholinophenyl) -butan-1-one, or 2- (4-bromo-benzyl-2-dimethylamino- 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one, and the like.
  • biimidazole-based compounds examples include 2,2-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis , 4 ', 5,5'-tetrakis (3,4,5-trimethoxyphenyl) -1,2'-biimidazole, 2,2'-bis (2,3-dichlorophenyl) 4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (o-chlorophenyl) -4,4,5,5'-tetraphenyl-1,2'-biimidazole and the like , But is not limited thereto.
  • the triazine-based compound may be at least one selected from the group consisting of 3- ⁇ 4- [2,4-bis (trichloromethyl) -s-triazin-6-yl] phenylthio ⁇ propionic acid, 1,1,1,3,3,3- (Trichloromethyl) -s-triazine-6-yl] phenylthio ⁇ propionate, ethyl 2- ⁇ 4- [2,4 Bis (trichloromethyl) -s-triazin-6-yl] phenylthio ⁇ acetate, 2- epoxyethyl-2- ⁇ 4- [ Yl] phenylthio ⁇ acetate, benzyl-2- ⁇ 4- [2- (4-fluorophenyl) (Trichloromethyl) -s-triazine-6-yl] phenylthio ⁇ acetate, 3- ⁇ chloro-4- [ (Phenylthio) propionic acid, 2,4- bis (trichloro
  • the oxime-based compound may be at least one selected from the group consisting of 1,2-octadione, -1- (4-phenylthio) phenyl, 2- (o-benzoyloxime) (Ciba Geigy, Shisei 124), ethanone, -Ethyl) -6- (2-methylbenzoyl-3-yl) -, 1- (O-acetyloxime) (Cajoo 242), N-1919 (Adeca), and the like.
  • the content of the binder resin is 1 wt% to 60 wt%, preferably 10 wt% to 25 wt%, based on the total weight of solid components in the photosensitive resin composition, Is 0.1 wt% to 20 wt%, preferably 1 wt% to 7 wt%, and the content of the polyfunctional monomer is 0.1 wt% to 50 wt%, preferably 5 wt% to 20 wt%.
  • the content of the solvent may be 10 to 85% by weight, preferably 35 to 65% by weight, based on the total weight of the composition.
  • the colorant dispersion may be contained in an amount of 5 to 35% by weight based on the total weight of the composition, and the content of the first and second xanthene dyes and the dispersant in the colorant dispersion may be 5 to 20% by weight.
  • the total weight of the solid content means the sum of the total weight of the components excluding the solvent in the resin composition.
  • the standard of weight percentage based on solid content and solid content of each component can be measured by general analytical means used in the art such as liquid chromatography or gas chromatography.
  • the above-mentioned photosensitive resin composition may further include at least one of a dye and a pigment.
  • a dye and a pigment examples of further included dyes and pigments are the same as those exemplified for the dyes and pigments further included in the colorant composition described above.
  • the photosensitive resin composition may further include a surface additive.
  • a surface additive a hardening accelerator, adhesion promoter, adhesion aid, surfactant, thermal polymerization inhibitor, ultraviolet absorber, dispersant, leveling agent, antioxidant, photo-crosslinking sensitizer, multi-thiol and the like may be used.
  • the surface additive may be contained in an amount of 0.1 to 5% by weight, preferably 0.5 to 1% by weight based on the total amount of the photosensitive resin composition.
  • the content of the surface additive may be 0.1% by weight to 20% by weight based on the total weight of the solid components in the photosensitive resin composition.
  • the photo-crosslinking sensitizer may be at least one selected from the group consisting of benzophenone, 4,4-bis (dimethylamino) benzophenone, 4,4-bis (diethylamino) benzophenone, 2,4,6-trimethylaminobenzophenone, Benzoate compounds such as benzoate, 3,3-dimethyl-4-methoxybenzophenone, and 3,3,4,4-tetra (t-butylperoxycarbonyl) benzophenone; Fluorene-based compounds such as 9-fluorenone, 2-chloro-9-proprenone and 2-methyl-9-fluorenone; Thioxanthone systems such as thioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 1-chloro-4-propyloxytioxanthone, isopropylthioxanthone and diisopropylthioxanthone compound; Xanthone compounds
  • curing accelerator curing and mechanical strength are used, and specifically, 2-mercaptobenzoimidazole, 2-mercaptobenzothiazole, 2- mercaptobenzoxazole, 2,5-dimercapto-1,3 , 4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, pentaerythritol-tetrakis (3-mercaptopropionate), pentaerythritol-tris (3-mercaptopropionate) (2-mercaptoacetate), trimethylolpropane-tris (2-mercaptoacetate), and trimethylolpropane-tris (3-mercaptopropionate) Nate) may be used.
  • adhesion promoter used in the present invention examples include methacryloyloxypropyltrimethoxysilane, methacryloyloxypropyldimethoxysilane, methacryloyloxypropyltriethoxysilane, methacryloyloxypropyldimethoxysilane , And at least one selected from the group consisting of octyltrimethoxysilane, dodecyltrimethoxysilane, octadecyltrimethoxysilane and the like as the alkyltrimethoxysilane can be used. You can choose to use it.
  • the silicone surfactant is BYK-077, BYK-085, BYK-300, BYK-301, BYK-302, BYK-306, BYK-307 , BYK-310, BYK-320, BYK-322, BYK-323, BYK-325, BYK-330, BYK-331, BYK-333, BYK-335, BYK-341v344, BYK-345v346, BYK-370, BYK-370, BYK-380, and BYK-390 may be used as the fluorine-based surfactant, and DIC F-444, F-444, F-441, F-450, F-493, F-494, F-443, F-444, F-445 and F-446 of Dai Nippon Ink & , F-470, F-471, F-472SF, F-474, F-475, F-477, F-478, F-479, F-480SF, F-482,
  • the antioxidant may be at least one selected from the group consisting of a hindered phenol antioxidant, an amine antioxidant, a thio antioxidant, and a phosphine antioxidant, but is not limited thereto.
  • antioxidants include phosphoric acid type heat stabilizers such as phosphoric acid, trimethyl phosphate or triethyl phosphate; Butyl-p-cresol, octadecyl-3- (4-hydroxy-3,5-di-t- butylphenyl) propionate, tetrabis [methylene- Butyl-4-hydroxyphenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3,5-di- 4-hydroxybenzylphosphite diethyl ester, 2,2-thiobis (4-methyl-6-t-butylphenol), 2,6-g, (3-methyl-6-t-butylphenol), 4,4'-thiobis (3-methyl- (4'-hydroxy-3'-tert-butylphenyl) butanoic acid] glycol ester (Bis [3,3- Hindered phenol-based primary antioxidants such as esters; Amines such as phenyl-?
  • UV absorber 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chloro-benzotriazole and alkoxybenzophenone may be used. Anything that is commonly used can be used.
  • thermal polymerization inhibitor examples include p-anisole, hydroquinone, pyrocatechol, t-butyl catechol, N-nitrosophenylhydroxyamine ammonium salt, N-nitrosophenylhydroxy (3-methyl-6-t-butylphenol), 2,2-dimethyl-2-pyrrolidone, But are not limited to, methylene bis (4-methyl-6-t-butylphenol), 2-mercaptoimidazole, and phenothiazine, And may include those generally known in the art.
  • the leveling agent may be polymeric or non-polymeric.
  • Specific examples of the polymeric leveling agent include polyethyleneimine, polyamide amine, reaction products of amine and epoxide, and specific examples of the non-polymeric leveling agent include non-polymer sulfur-containing and non-polymer nitrogen- But are not limited to, compounds commonly used in the art may all be used.
  • Another embodiment of the present invention provides a color filter comprising a transparent substrate and a colored layer provided on the transparent substrate, wherein the colored layer comprises a cured product of the photosensitive resin composition described above.
  • the color filter can be produced using the photosensitive resin composition.
  • the photosensitive resin composition is coated on a substrate to form a coating film, and the color filter can be formed by exposing, developing and curing the coating film.
  • the coating method is not particularly limited, but a spray method, a roll coating method, a spin coating method, or the like can be used, and generally, a spin coating method is widely used. After the coating film is formed, a part of the residual solvent may be removed under reduced pressure as occasion demands.
  • Examples of the light source for curing the resin composition according to the present invention include, but are not limited to, a mercury vapor arc, a carbon arc, and an Xe arc that emits light having a wavelength of 250 nm to 450 nm.
  • the resin composition according to one embodiment of the present invention can provide a color filter having a high color reproducibility and a high luminance and a high contrast ratio even when the color filter is cured during the production of the color filter due to its excellent heat resistance, have.
  • the substrate may be a glass plate, a silicon wafer, a plate of a plastic substrate such as polyethersulfone (PES), polycarbonate (PC), or the like, and the kind thereof is not particularly limited.
  • a plastic substrate such as polyethersulfone (PES), polycarbonate (PC), or the like, and the kind thereof is not particularly limited.
  • the color filter may include a red pattern, a green pattern, a blue pattern, and a black matrix.
  • the color filter may further include an overcoat layer.
  • a lattice-shaped black pattern called a black matrix can be arranged for the purpose of improving the contrast.
  • chromium can be used as the material of the black matrix.
  • a method of depositing chromium on the entire glass substrate and forming a pattern by an etching process can be used.
  • a resin black matrix by a pigment dispersion method capable of fine processing can be used.
  • the black matrix according to one embodiment of the present invention can use a black pigment or a black dye as a coloring material.
  • a black pigment or a black dye as a coloring material.
  • carbon black may be used alone, or a mixture of carbon black and a color pigment may be used.
  • the color pigment having insufficient light shielding property is mixed, the strength of the film or the adhesion to the substrate is lowered There is an advantage not to be.
  • a liquid crystal display including the color filter according to the present invention is provided.
  • the liquid crystal display device may have a configuration known in the art, except that it includes the color filter described above.
  • methyl methacrylate 45.8 parts by weight of methyl methacrylate, 14.8 parts by weight of n-butyl methacrylate, 7.8 parts by weight of 2-ethylhexyl methacrylate, and 5.0 parts by weight of benzyl methacrylate, based on 100 parts by weight of the monomer or polymerization initiator, , 3.0 parts by weight of triethylene glycol methyl ether methacrylate, 18.9 parts by weight of 2-dimethylaminoethyl methacrylate, and 4.7 parts by weight of benzyl chloride salt were uniformly added, and the mixture was added to a dropping funnel. And the mixture was added dropwise to the flask over 2 hours.
  • the polymerization yield was 98.7% or more and the weight average molecular weight (Mw) was 5,500.
  • Mw weight average molecular weight
  • 10 parts by weight of propylene glycol monomethyl ether was added based on 100 parts by weight of the total weight of the dispersing agent including the resin having a cationic group in the side chain, and a resin having cationic groups was prepared in the side chain of 5 mol% Respectively.
  • the amine value of the obtained resin was 30 mgKOH / g.
  • the weight average molecular weight (Mw) of the resin having a cationic group in the side chain was measured by gel permeation chromatography (GPC) using polystyrene as a standard material. Further, the amine value was determined by the potentiometric titration method using 0.1N hydrochloric acid aqueous solution, and then converted to the equivalent amount of potassium hydroxide.
  • Resins A-2 to A-8 having cationic groups in the side chain were obtained in the same manner as in Production Example 1 except that the monomer, the polymerization initiator and the reaction temperature were changed to the compositions shown in Table 1
  • MMA is methyl methacrylate
  • nBMA is n-butyl methacrylate
  • EHMA is ethylhexyl methacrylate
  • BzMA is benzyl methacrylate
  • TEGMA is triethylene aminoethyl methacrylate
  • DMAEMA is dimethyl Aminoethyl methacrylate
  • BC is benzyl chloride salt
  • ST is styrene
  • MDGMA is diethylene glycol methyl ether methacrylate
  • EG is ethylene glycol methacrylate.
  • the composition shown in Table 1 was placed in a Bench Kneader (Irie shokai co.ltd. Model PBV-01) together with 7.5 g of diethylene glycol and 40 g of crushed salt (NaCl) and refined for 4 hours. After 4 hours, the micronized colorant composition was added to 1 L of distilled water at 60 ⁇ , stirred for 30 minutes, and then decompressed to remove distilled water. When distilled water was removed under reduced pressure, about 7 L of distilled water at 60 ° C was further used to completely remove the salt (NaCl) to obtain the complexes B-1 to B-21 shown in Table 2 below. The following structures were used as the first and second xanthene dyes.
  • the mole ratio (%) in Table 2 means the ratio of the ammonium salt introduced by the ratio of EG (ethylene glycol methacrylate) in Table 1 above.
  • Composites B-1 to B-21 which were the colorant compositions prepared above, were stirred so as to homogeneously mix the composition shown in the following Table 3 and 8.4 g of propylene glycol monomethyl ether acetate, and then granulated using 0.3 mm diameter zirconia beads to obtain Paint The dispersion treatment was carried out with a shaker for 2 hours. Then, the dispersion was changed to 0.1 mm zirconia beads and further dispersed with a paint shaker for 2 hours. After the dispersion treatment, 12.6 g of propylene glycol monomethyl ether acetate was added to each composition, followed by filtration with a 1.0- ⁇ m filter to obtain a colorant dispersion.
  • the photosensitive coloring composition was prepared by applying the components and blending amounts shown in Table 4 below.
  • Binder A was the same as that used for preparing the colorant dispersion.
  • the obtained colorant dispersions (C-1 to C-21) were evaluated for particle size and storage stability by the following methods.
  • a 1 cm X 5 cm quartz cell was filled with PGMEA (propylene glycol monomethyl ether acetate) at about one-quarter of the height, and about 1 to 2 drops of the prepared colorant dispersion was dropped.
  • PGMEA propylene glycol monomethyl ether acetate
  • the degree of refinement was evaluated based on the particle size measurement results. The results of the particle size measurement are shown in Table 5 below.
  • Dispersions C-9 to C-21 obtained by micronization using a dispersant containing a first xanthene dye, a second xanthene dye and an ammonium structure were dispersed in a colorant dispersion liquid having a particle size of 40 to 80 nm .
  • the initial viscosity of the colorant dispersion at 25 ° C on the day when the colorant dispersion was prepared and the viscosity after preservation in convection oven at 40 ° C for 7 days were measured using a viscometer (Toki Sangyo Viscometer TV-25) at a revolution of 100 rpm .
  • the rate of change in viscosity with time was calculated based on the following formula.
  • the storage stability was evaluated based on the following criteria. The evaluation results are shown in Table 6 below.
  • the dispersions C-9 and C-12 to C-21 were prepared by making a composite using a dispersant containing a first xanthene dye, a second xanthene dye and an ammonium structure and applying a dispersant containing an ammonium structure to the dispersion.
  • the viscosity stability was excellent and it was in a range that can be preferably used as a color filter.
  • the prepared photosensitive coloring composition Comparative Example 5 and Examples 1 to 13 were spin-coated on a 5 cm x 5 cm Glass and pre-baked at 110 ° C for 75 seconds to form a film.
  • the distance between the substrate on which the film was formed and the photo mask was set to 250 mu m, and an exposure amount of 40 mJ / cm < 2 >
  • the exposed substrate was developed in a developing solution (KOH, 0.05%) for 60 seconds and then heat-treated at 230 ⁇ for 20 minutes to obtain a color pattern.
  • the color patterns were measured with a spectrophotometer (MCPD) to obtain the transmittances of Comparative Examples 1 to 8 and Examples 1 to 13.
  • the substrate was further heat treated in a convection oven at 230 ° C for 5 hours and 30 minutes, And the value of? Eab was confirmed.
  • Examples 1 to 13 in which fineness was obtained by combining a first xanthene dye and a dispersant containing a second xanthene dye and an ammonium structure were excellent in the degree of improvement of the degree of transparency.
  • a dispersant containing an ammonium structure was superior in heat resistance.
  • a colorant dispersion is prepared by applying a first xanthene dye having the same number of positive charges and negative charges and a second xanthene dye having a negative charge more than 1 positive charge and an ammonium structure to form a colorant dispersion,
  • the viscosity stability and the brightness of the coating film were high.

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Abstract

La présente invention concerne une composition de colorants, une dispersion de colorants, une composition de résine photosensible, un filtre coloré et un afficheur à cristaux liquides. La composition de colorants comprend : un premier colorant à base de xanthène ayant le même nombre de charges positives et de charges négatives; et un complexe qui est ioniquement lié à un second colorant à base de xanthène ayant un certain nombre de charges négatives qui est au moins supérieur d'une unité au nombre de charges positives, et un agent dispersant qui a un indice d'amine de 0 à 200 mg de KOH/g et comprend une structure d'ammonium.
PCT/KR2018/007001 2017-11-28 2018-06-21 Composition de colorants, dispersion de colorants, composition de résine photosensible, filtre coloré et afficheur à cristaux liquides Ceased WO2019107687A1 (fr)

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CN201880003035.7A CN110099966B (zh) 2017-11-28 2018-06-21 着色剂组合物、着色剂分散液、感光性树脂组合物、滤色器和液晶显示装置

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KR102400637B1 (ko) * 2019-11-04 2022-05-23 주식회사 케이디파인켐 열전달 유체용 착색제 및 이를 포함하는 조성물
KR102782512B1 (ko) * 2019-12-10 2025-03-14 주식회사 엘지화학 블랙 절연막용 감광성 조성물, 블랙 절연막, 및 디스플레이 장치
JP7527925B2 (ja) * 2019-12-17 2024-08-05 保土谷化学工業株式会社 キサンテン色素の製造方法

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TWI695035B (zh) 2020-06-01
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