CN108285652B - Pigment dispersion composition, colored photosensitive resin composition and use thereof - Google Patents

Pigment dispersion composition, colored photosensitive resin composition and use thereof Download PDF

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Publication number
CN108285652B
CN108285652B CN201711298877.3A CN201711298877A CN108285652B CN 108285652 B CN108285652 B CN 108285652B CN 201711298877 A CN201711298877 A CN 201711298877A CN 108285652 B CN108285652 B CN 108285652B
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boiling point
photosensitive resin
solubility parameter
resin composition
colored photosensitive
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CN108285652A (en
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尹钟元
柳在范
李商范
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Dongwoo Fine Chem Co Ltd
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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
    • 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
    • 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
    • C09B67/006—Preparation of organic pigments
    • 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
    • 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
    • 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
    • G03F7/0005—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
    • 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
    • G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
    • 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

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

Abstract

The present invention provides a pigment dispersion composition, a colored photosensitive resin composition and an application thereof, more specifically, the pigment dispersion composition is characterized by comprising a colorant and a first solvent, wherein the colorant comprises C.I. pigment yellow 185, and the first solvent comprises Propylene Glycol Monomethyl Ether Acetate (PGMEA); and more than one substance with a boiling point of more than 170 ℃ and a Hansen solubility parameter of 20-24.

Description

Pigment dispersion composition, colored photosensitive resin composition and use thereof
Technical Field
The invention relates to a pigment dispersion composition, a colored photosensitive resin composition, a color filter and an image display device comprising the color filter.
Background
Color filters are widely used in image pickup devices, liquid crystal display devices, and the like, and their application range is rapidly expanding. Color filters used in color liquid crystal display devices, imaging elements, and the like are generally manufactured as follows: a colored photosensitive resin composition containing colorants corresponding to red, green, and blue colors is uniformly applied by spin coating on a substrate on which a black matrix pattern is formed, and then the resultant is dried by heating (hereinafter, also referred to as "pre-baking"), and the resulting coating film is exposed to light and developed, and if necessary, further cured by heating (hereinafter, also referred to as "post-baking") repeatedly for each color, thereby forming pixels of each color. At this time, a Vacuum Dry (VD) process, which is a solvent removal process of the resist, is performed immediately after coating.
Currently, as one of the main CF substrate manufacturing methods, a color resist is coated by a Slit (Slit) coating method, and a VD process after coating is performed to increase a Vacuum (Vacuum) capacity larger than that of a conventional one to shorten a time of VD single-process time (Tact time) as a solvent removal time, thereby improving productivity. However, since rapid drying of the resist occurs with the decompression of the high vacuum, surface defects such as VD streaks (although VD streaks are expressed in various shapes, they are mainly generated in the shape of crater streaks, and therefore, unless otherwise mentioned, the VD streaks and the crater streaks are described as the same streaks). Therefore, there is a demand for a highly sensitive colored photosensitive resin composition capable of forming a uniform coating film even when a high vacuum is applied to the composition under reduced pressure.
As a method for solving the above-mentioned problems, a method of suppressing VD streaks (crater streaks) using a high-boiling solvent can be used, but there is a problem that VD increases the number of man-hours per unit time because the evaporation rate of the solvent is slow.
In recent years, pixels having high color density have been required, and the content of pigments and carbon black used in a colored photosensitive resin composition has been increased, so that fluidity during drying is deteriorated and VD mottle (crater mottle) is increased.
Korean laid-open patent No. 10-2016-.
Documents of the prior art
Patent document
Patent document 1: korean laid-open patent No. 10-2016-0112615 (2016.09.28 Tomitomo Fine chemical Co., Ltd.)
Disclosure of Invention
Problems to be solved
The present invention has been made to solve the above-described problems, and an object of the present invention is to provide a pigment-dispersed composition, a colored photosensitive resin composition, a color filter, and an image display device including the color filter, which are excellent in coatability and compatibility without generating foreign matters, VD unevenness, or PIN unevenness, which may occur in a process of manufacturing the color filter.
Means for solving the problems
The pigment-dispersion composition of the present invention for achieving the above object is characterized by comprising a colorant and a first solvent, the colorant comprising c.i. pigment yellow 185, the first solvent comprising PGMEA; and more than one substance with a boiling point of more than 170 ℃ and a Hansen (Hansen) solubility parameter of 20-24.
Further, the colored photosensitive resin composition of the present invention is characterized by comprising the above pigment dispersion composition and further comprising one or more selected from the group consisting of an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, a second solvent and an additive.
The present invention is also characterized by a color filter comprising a cured product of the colored photosensitive resin composition and an image display device comprising the color filter.
Effects of the invention
As described above, the pigment-dispersion composition of the present invention has the effect of preventing the occurrence of foreign matter, VD mottle, or PIN mottle which may be generated in the color filter production process and being excellent in coatability and compatibility by using a specific solvent.
The color filter manufactured by the colored photosensitive resin composition and the image display device comprising the color filter have the advantages of high productivity and no display defect.
Detailed Description
The present invention will be described in more detail below.
The pigment dispersion composition is described in detail below.
< pigment Dispersion composition >
The pigment dispersion composition is characterized by comprising a colorant and a first solvent, wherein the colorant comprises c.i. pigment yellow 185, and the first solvent comprises PGMEA; and more than one substance with a boiling point of more than 170 ℃ and a Hansen solubility parameter of 20-24.
Coloring agent
The above colorant comprises c.i. pigment yellow 185, and may further comprise one or more organic pigments generally used in the art. The pigment may be any of various pigments used in printing inks, inkjet inks, and the like, and specific examples thereof include water-soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, isoindoline pigments, perylene pigments, and the likePigment, pyrene ketone pigment, II
Figure BDA0001500824370000031
Oxazine pigments, anthraquinone pigments, dianthraquinone-based pigments, anthrapyrimidine pigments, anthraxanthone (anthanthrone) pigments, indanthrone (indanthrone) pigments, flavanthrone pigments, pyranthrone (pyranthrone) pigments, diketopyrrolopyrrole pigments, and the like. In particular, as The organic pigment, there may be mentioned, specifically, compounds classified as pigments in color index (published by The society of Dyers and Colourists), more specifically, pigments numbered by The following color index (c.i.), but The organic pigment is not limited thereto, and they may be used singly or in combination of two or more kinds.
Pigment yellow 13, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173 and 180
C.i. pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65 and 71
C.i. pigment red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 208, 215, 216, 224, 242, 254, 255 and 264
C.i. pigment green 7, 10, 15, 25, 36, 47 and 58, etc
The above-mentioned pigment may use organic pigments generally used in the art, and they may be used each alone or in combination of two or more.
Among the above-exemplified c.i. pigments, pigments selected from the group consisting of c.i. pigment yellow 138, c.i. pigment yellow 139, c.i. pigment yellow 150, c.i. pigment orange 38, c.i. pigment red 122, c.i. pigment red 166, c.i. pigment red 177, c.i. pigment red 208, c.i. pigment red 242, c.i. pigment red 254, c.i. pigment red 255, c.i. pigment green 7, c.i. pigment green 36, c.i. pigment green 58, and c.i. pigment green 59 can be preferably used.
A first solvent
The first solvent is characterized by being a mixed solvent of propylene glycol monomethyl ether acetate and more than one solvent with a boiling point of more than 170 ℃ and a Hansen solubility parameter of 20-24.
The hansen Solubility Parameter (SP) is an evaluation value of cohesive energy density, and generally, the stronger the polarity of a solvent, the larger the solubility parameter value.
The first solvent having a boiling point (b.p) of 170 ℃ or higher and a hansen Solubility Parameter (SP) of 20 to 24 may include one or more selected from the group consisting of ethylene glycol butyl ether (EGBE, b.p.171, SP 20.8), ethylene glycol phenyl ether (EGPE, b.p.247, SP 23.5), ethylene glycol hexyl ether (EGHE, b.p.208, SP 20.6), 3-methoxy-3-methyl-1-butanol (MMB, b.p.175, SP 20.2), propylene glycol phenyl ether (PGPE, b.p.241, SP 21.5), dipropylene glycol methyl ether (DPGME, b.p.190, SP 20), diethylene glycol methyl ether (DEGME, b.p.194, SP 22), diethylene glycol ethyl ether (DEGEE, b.p.202, SP 22.2), diethylene glycol butyl ether (DEGBE, b.p.230, SP 20.4), triethylene glycol methyl ether (TEGME, b.p.249, triethylene glycol ethyl ether (gesp) 256, SP 20.4), triethylene glycol methyl ether (TEGME, b.p.249, 7.p.256, SP).
< colored photosensitive resin composition >
The colored photosensitive resin composition of the present invention includes the above pigment-dispersion composition, and may further include one or more selected from the group consisting of an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, a second solvent, and an additive.
Alkali soluble resin
The alkali-soluble resin is produced by copolymerizing an ethylenically unsaturated monomer having a carboxyl group as an essential component in order to be soluble in an alkali developer used in a developing step in forming a pattern.
In addition, in order to ensure the development speed and the storage stability of the colored photosensitive resin composition, the acid value of the alkali-soluble resin is preferably 30 to 150 mgKOH/g. When the acid value of the alkali-soluble resin is less than 30mgKOH/g, it is difficult to secure a sufficient development speed in the colored photosensitive resin composition, and when it exceeds 150mgKOH/g, adhesion to the substrate is reduced, short-circuiting of the pattern is likely to occur, storage stability of the colored photosensitive resin composition is lowered, and viscosity is likely to increase.
Specific examples of the ethylenically unsaturated monomer having a carboxyl group include monocarboxylic acids such as acrylic acid, methacrylic acid, and crotonic acid; dicarboxylic acids such as fumaric acid, mesaconic acid, and itaconic acid; and anhydrides of these dicarboxylic acids; and mono (meth) acrylates of polymers having carboxyl groups and hydroxyl groups at both ends, such as ω -carboxy polycaprolactone mono (meth) acrylate, and acrylic acid and methacrylic acid are preferred.
The alkali-soluble resin can be produced by copolymerizing an ethylenically unsaturated monomer having a carboxyl group and an ethylenically unsaturated monomer having a hydroxyl group in order to provide a hydroxyl group to the alkali-soluble resin, or can be produced by further reacting a copolymer of a compound having a glycidyl group and an ethylenically unsaturated monomer having a carboxyl group. Further, the compound having a glycidyl group can be produced by reacting a copolymer of an ethylenically unsaturated monomer having a carboxyl group and an ethylenically unsaturated monomer having a hydroxyl group.
Specific examples of the compound having a glycidyl group include butyl glycidyl ether, glycidyl propyl ether, glycidyl phenyl ether, 2-ethylhexyl glycidyl ether, glycidyl butyrate, glycidyl methyl ether, ethyl glycidyl ether, glycidyl isopropyl ether, tert-butyl glycidyl ether, benzyl glycidyl ether, 4-tert-butyl glycidyl formate, glycidyl stearate, aryl glycidyl ether, and glycidyl methacrylate, and preferably butyl glycidyl ether, aryl glycidyl ether, and glycidyl methacrylate, and two or more of these compounds may be used in combination.
The unsaturated monomer copolymerizable in the production of the alkali-soluble resin is exemplified below, but not limited thereto.
Specific examples of the copolymerizable unsaturated bond-containing polymerizable monomer include aromatic vinyl compounds such as styrene, vinyltoluene, α -methylstyrene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzylmethyl ether, m-vinylbenzylmethyl ether, p-vinylbenzylmethyl ether, o-vinylbenzylglycidyl ether, m-vinylbenzylglycidyl ether and p-vinylbenzylglycidyl ether, N-cyclohexylmaleimide, N-benzylmaleimide, N-phenylmaleimide, N-o-hydroxyphenylmaleimide, N-m-hydroxyphenylmaleimide, N-p-hydroxyphenylmaleimide, N-o-methoxyphenylmaleimide, N-m-methoxyphenylmaleimide, N-p-methoxyphenylmaleimide and other N-substituted maleimide compounds such as methyl (meth) acrylate, ethyl (meth) acrylate, N-propyl (meth) acrylate, N-butyl (meth) acrylate, N-p-methoxyphenylmaleimide, N-methoxyphenylmaleimide, 2- (2-epoxybutyl) acrylate, 2- (2-epoxybutyl) methacrylate, 3-2- (2-epoxybutyl) acrylate, 3- (2-epoxybutyl) methacrylate, 3-epoxybutyl) acrylate, 3- (2-epoxybutyl) acrylate, 3-epoxybutyl) acrylate, and other (2-epoxybutyl) methacrylate, 3-epoxybutyl) acrylate, 3-epoxybutyl methacrylate, and other (methyl-epoxybutyl) acrylate, 3-epoxybutyl methacrylate, and other unsaturated methacrylate, and other (2-epoxybutyl) acrylate compounds such as well as the like, (2-epoxybutyl) acrylate, 2-epoxybutyl methacrylate, 4-epoxybutyl acrylate, 2-epoxybutyl methacrylate, 4-epoxybutyl methacrylate, 2-epoxybutyl acrylate, 2-epoxybutyl methacrylate, 4-epoxybutyl methacrylate, 2-epoxybutyl acrylate.
The copolymerizable polymerizable monomers having an unsaturated bond may be used each alone or in combination of two or more.
The content of the alkali-soluble resin is 10 to 80 wt%, preferably 10 to 70 wt%, based on the solid content of the photosensitive resin composition. If the content of the alkali-soluble resin is within the above range, the solubility in a developer is sufficient, and a pattern is easily formed, and it is preferable to prevent the film from decreasing in the pixel portion of the exposed portion and to prevent the peeling off in the pixel portion during development.
Photopolymerizable compound
The photopolymerizable compound is a compound polymerizable by the action of the photopolymerization initiator described below, and a monofunctional monomer, a difunctional monomer, or a polyfunctional monomer may be used, and preferably a polyfunctional monomer having two or more functionalities may be used.
Specific examples of the monofunctional monomer include, but are not limited to, nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, and N-vinylpyrrolidone.
Specific examples of the bifunctional monomer include, but are not limited to, 1, 6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, bis (acryloyloxyethyl) ether of bisphenol a, and 3-methylpentanediol di (meth) acrylate.
Specific examples of the polyfunctional monomer include, but are not limited to, trimethylolpropane tri (meth) acrylate, ethoxylated trimethylolpropane tri (meth) acrylate, propoxylated trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, ethoxylated dipentaerythritol hexa (meth) acrylate, propoxylated dipentaerythritol hexa (meth) acrylate, and dipentaerythritol hexa (meth) acrylate.
The content of the photopolymerizable compound is preferably 5 to 45 wt% and more preferably 7 to 45 wt% in terms of wt% relative to the solid content in the colored photosensitive resin composition. When the content of the photopolymerizable compound is within the above range, the intensity and smoothness of the pixel portion are preferably improved.
Light collectionSynthetic initiators
The photopolymerization initiator is not particularly limited in kind as long as it can polymerize the photopolymerizable compound. In particular, from the viewpoint of polymerization characteristics, initiation efficiency, absorption wavelength, availability, price, and the like, it is preferable to use one or more compounds selected from the group consisting of acetophenone compounds, benzophenone compounds, triazine compounds, bisimidazole compounds, oxime compounds, and thioxanthone compounds as the photopolymerization initiator.
Specific examples of the acetophenone-based compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzildimethylketal, 2-hydroxy-1- [4- (2-hydroxyethoxy) phenyl ] -2-methylpropan-1-one, 1-hydroxycyclohexylphenylketone, 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one, 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl ] propan-1-one, and mixtures thereof, 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one, and the like.
Examples of the benzophenone-based compound include benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4 ' -methyldiphenyl sulfide, 3 ', 4,4 ' -tetrakis (t-butylperoxycarbonyl) benzophenone, and 2,4, 6-trimethylbenzophenone.
Specific examples of the triazine compound include 2, 4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6- (4-methoxynaphthyl) -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6-piperonyl-1, 3, 5-triazine, 2, 4-bis (trichloromethyl) -6- (4-methoxystyryl) -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) vinyl ] -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6- [2- (furan-2-yl) Yl) vinyl ] -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) vinyl ] -1,3, 5-triazine, 2, 4-bis (trichloromethyl) -6- [2- (3, 4-dimethoxyphenyl) vinyl ] -1,3, 5-triazine, and the like.
Specific examples of the biimidazole compound include 2,2 '-bis (2-chlorophenyl) -4,4,5, 5' -tetraphenylbiimidazole, 2 '-bis (2, 3-dichlorophenyl) -4, 4', 5,5 '-tetraphenylbiimidazole, 2' -bis (2-chlorophenyl) -4,4 ', 5, 5' -tetrakis (alkoxyphenyl) biimidazole, 2,2 '-bis (2-chlorophenyl) -4, 4', 5,5 '-tetrakis (trialkoxyphenyl) biimidazole, 2-bis (2, 6-dichlorophenyl) -4, 4', 5,5 '-tetraphenyl-1, 2' -biimidazole, or imidazole compounds in which the phenyl group at the 4,4 ', 5, 5' position is substituted with an alkoxycarbonylyl group, and the like. Among them, 2' -bis (2-chlorophenyl) -4,4 ', 5,5 ' -tetraphenyl biimidazole, 2' -bis (2, 3-dichlorophenyl) -4,4 ', 5,5 ' -tetraphenyl biimidazole, 2-bis (2, 6-dichlorophenyl) -4,4 ', 5,5 ' -tetraphenyl-1, 2' -biimidazole are preferably used.
Specific examples of the oxime compounds include o-ethoxycarbonyl- α -oxyimino-1-phenylpropan-1-one, and typical examples of commercially available oxime compounds include OXE01 and OXE02 from Pasteur.
Examples of the thioxanthone-based compound include 2-isopropylthioxanthone, 2, 4-diethylthioxanthone, 2, 4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.
In order to improve the sensitivity of the colored photosensitive resin composition of the present invention, the photopolymerization initiator may further contain a photopolymerization initiation aid. The colored photosensitive resin composition of the present invention contains a photopolymerization initiation aid, so that the sensitivity is further improved and the productivity can be improved.
The photopolymerization initiator may be, for example, one or more compounds selected from the group consisting of amine compounds, carboxylic acid compounds, and organic sulfur compounds having a thiol group.
As the amine compound, an aromatic amine compound is preferably used, and specifically, an aliphatic amine compound such as triethanolamine, methyldiethanolamine, triisopropanolamine, or the like; methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, N-dimethyl-p-toluidine, 4 ' -bis (dimethylamino) benzophenone (known as Michler's ketone), 4 ' -bis (diethylamino) benzophenone, and the like.
The carboxylic acid compound is preferably an aromatic heteroacetic acid, and specific examples thereof include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthyloxyacetic acid and the like.
Specific examples of the organic sulfur compound having a thiol group include 2-mercaptobenzothiazole, 1, 4-bis (3-mercaptobutyryloxy) butane, 1,3, 5-tris (3-mercaptobutoxyethyl) -1,3, 5-triazine-2, 4,6(1H,3H,5H) -trione, trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptobutyrate), pentaerythritol tetrakis (3-mercaptopropionate), dipentaerythritol hexa (3-mercaptopropionate), tetraethyleneglycol bis (3-mercaptopropionate), and the like.
The content of the photopolymerization initiator may be 0.1 to 40% by weight, preferably 1 to 30% by weight, based on the total weight% of the solid content of the colored photosensitive resin composition of the present invention, relative to the contents of the alkali-soluble resin and the photopolymerizable compound. When the content of the photopolymerization initiator is within the above range, the colored photosensitive resin composition is preferably highly sensitive to shorten the exposure time, improve the productivity, and maintain the high resolution. Further, the strength of the pixel portion and the smoothness of the surface of the pixel portion formed using the composition under the above conditions can be improved.
When the photopolymerization initiator is further used, the content of the photopolymerization initiator may be 0.1 to 40% by weight, preferably 1 to 30% by weight, based on the total weight% of the solid content of the colored photosensitive resin composition of the present invention, relative to the contents of the alkali-soluble resin and the photopolymerizable compound. When the amount of the photopolymerization initiator is within the above range, the sensitivity of the colored photosensitive resin composition is further improved, and the productivity of a color filter formed using the composition is improved.
A second solvent
The second solvent is not particularly limited, and various organic solvents used in the art may be used.
Specific examples of the second solvent include ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether; diethylene glycol dialkyl ethers such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, and diethylene glycol dibutyl ether; ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate; alkylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate, and methoxypentyl acetate; aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene; ketones such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, and cyclohexanone; alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerol; esters such as ethyl 3-ethoxypropionate and methyl 3-methoxypropionate; cyclic esters such as γ -butyrolactone.
Additive agent
The additive contained in the colored photosensitive resin composition of the present invention may be selectively added as needed, and examples thereof include other polymer compounds, surfactants, adhesion promoters, antioxidants, ultraviolet absorbers, and anti-gelling agents.
Specific examples of the other polymer compounds include curable resins such as epoxy resins and maleimide resins; and thermoplastic resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, and polyurethane.
The surfactant may be used for further improving the film formability of the photosensitive resin composition, and a fluorine-based surfactant, a silicone-based surfactant, or the like may be preferably used.
Examples of the silicone surfactants include commercially available silicone surfactants such as DC3PA, DC7PA, SH11PA, SH21PA and SH8400 available from Dow Corning Tokyo Silicones, TSF-4440, TSF-4300, TSF-4445, TSF-4446, TSF-4460 and TSF-4452 available from GE Toshiba Silicones. Examples of the fluorine-containing surfactant include MEGAFAC F-470, F-471, F-475, F-482 and F-489, which are commercially available from Dainippon ink chemical industries. The above-exemplified surfactants may be used each alone or in combination of two or more.
Specific examples of the adhesion promoters include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, and, 3-isocyanatopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, and the like. The adhesion promoters exemplified above may be used each alone or in combination of two or more. The content of the adhesion promoter may be 0.01 to 10% by weight, preferably 0.05 to 2% by weight, based on the total weight of the solid content of the colored photosensitive resin composition.
Specific examples of the antioxidant include 2,2' -thiobis (4-methyl-6-tert-butylphenol) and 2, 6-di-tert-butyl-4-methylphenol.
Specific examples of the ultraviolet absorber include 2- (3-tert-butyl-2-hydroxy-5-methylphenyl) -5-chlorobenzotriazole and alkoxybenzophenone.
Specific examples of the anti-gelling agent include sodium polyacrylate and the like.
< color Filter >
The present invention provides a color filter produced from the colored photosensitive resin composition.
The color filter includes a substrate and a pattern layer formed on the substrate.
The substrate is not particularly limited, and the color filter itself may be the substrate, or may be a position where the color filter is located in a display device or the like. The substrate may be glass, silicon (Si), silicon oxide (SiOx), or a polymer substrate, and the polymer substrate may be polyether sulfone (PES), Polycarbonate (PC), or the like.
The pattern layer as a layer containing the photosensitive resin composition of the present invention may be a layer formed by applying the above photosensitive resin composition and performing exposure, development and heat curing in a predetermined pattern.
The pattern layer formed of the colored photosensitive resin composition may include a red pattern layer containing red quantum dot particles, a green pattern layer containing green quantum dot particles, and a blue pattern layer containing blue quantum dot particles. When the light is irradiated, the red pattern layer emits red light, the green pattern layer emits green light, and the blue pattern layer emits blue light.
In this case, when the light source is applied to an image display device, the light emitted from the light source is not particularly limited, but a light source emitting blue light may be used in view of more excellent color reproducibility.
According to another embodiment of the present invention, the pattern layer may include only two color pattern layers of a red pattern layer, a green pattern layer, and a blue pattern layer. In this case, the pattern layer further includes a transparent pattern layer containing no quantum dot particles.
In the case of providing only two color pattern layers, a light source that emits light having a wavelength other than the two colors may be used. For example, in the case of including a red pattern layer and a green pattern layer, a light source that emits blue light may be used. In this case, the red quantum dot particles emit red light, the green quantum dot particles emit green light, and the transparent pattern layer directly transmits blue light to display blue.
The color filter including the above substrate and pattern layer may further include partition walls formed between the patterns, or may further include a black matrix. In addition, the color filter may further include a protective film formed on the upper portion of the pattern layer of the color filter.
< image display apparatus >
The present invention provides an image display device including the color filter.
The color filter of the present invention can be applied not only to a general image display device but also to various image display devices such as an electroluminescence display device, a plasma display device, and a field emission display device.
The image display device of the present invention may include a color filter including a red pattern layer containing red quantum dot particles, a green pattern layer containing green quantum dot particles, and a blue pattern layer containing blue quantum dot particles. In this case, when the light source is applied to an image display device, the light emitted from the light source is not particularly limited, but a light source emitting blue light is preferably used in view of more excellent color reproducibility.
According to another embodiment of the present invention, the image display device of the present invention may further include a color filter including only two color pattern layers of a red pattern layer, a green pattern layer, and a blue pattern layer. In this case, the color filter further includes a transparent pattern layer containing no quantum dot particles.
In the case of providing only two color pattern layers, a light source that emits light having a wavelength other than the two colors may be used. For example, in the case of including a red pattern layer and a green pattern layer, a light source that emits blue light may be used. In this case, the red quantum dot particles emit red light, the green quantum dot particles emit green light, and the transparent pattern layer directly transmits blue light to display blue.
The present invention will be described in more detail below with reference to examples. However, the following examples are merely intended to illustrate the present invention more specifically, and the scope of the present invention is not limited to the following examples. The following embodiments may be appropriately modified and changed by those skilled in the art within the scope of the present invention.
Preparation example: production of pigment Dispersion composition
Pigment dispersion compositions were prepared by mixing and dispersing the components and contents shown in table 1 below for 12 hours by a bead mill.
[ Table 1]
Figure BDA0001500824370000121
Synthesis example: synthesis of alkali soluble resins
A flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel and a nitrogen gas inlet tube was prepared, while 74.8g (0.20 mol) of benzylmaleimide, 43.2g (0.30 mol) of acrylic acid, 118.0g (0.50 mol) of vinyl toluene, 4g of t-butyl peroxy-2-ethylhexanoate and 40g of Propylene Glycol Monomethyl Ether Acetate (PGMEA) were charged into the flask via the monomer dropping funnel, and then stirred and mixed, and 6g of n-dodecanethiol and 24g of PGMEA were added to the flask via a chain transfer agent dropping vessel. Thereafter, 395g of PGMEA was introduced into the flask, the atmosphere in the flask was changed from air to nitrogen, and then the temperature of the flask was raised to 90 ℃ while stirring. Subsequently, the monomer and the chain transfer agent were dropped from the dropping funnel. During the dropping, the temperature was raised to 110 ℃ for 1 hour and maintained for 3 hours while maintaining 90 ℃ respectively, and then introduced into a gas introduction tube to start bubbling of an oxygen/nitrogen (5/95 (v/v) mixed gas. Subsequently, 28.4g of glycidyl methacrylate [ (0.10 mol%) ], 0.4g of 2,2' -methylenebis (4-methyl-6-tert-butylphenol) and 0.8g of triethylamine were placed in a flask, and the reaction was continued at 110 ℃ for 8 hours to obtain a resin B having a solid acid value of 70 mg KOH/g. The weight average molecular weight in terms of polystyrene measured by GPC was 16,000, and the molecular weight distribution (Mw/Mn) was 2.3.
The weight average molecular weight (Mw) and the number average molecular weight (Mn) were measured by GPC under the following conditions.
The device comprises the following steps: HLC-8120GPC (manufactured by Tosoh corporation)
Column: TSK-GELG4000HXL + TSK-GELG2000HXL (series connection)
Column temperature: 40 deg.C
Mobile phase solvent: tetrahydrofuran (THF)
Sulfur rate: 1.0 ml/min
Injection amount: 50 μ l
A detector: RI (Ri)
And (3) measuring the concentration of the sample: 0.6% by mass (solvent ═ tetrahydrofuran)
Calibration standard substance: TSK Standard polystyrenes F-40, F-4, F-1, A-2500, A-500 (manufactured by Tosoh corporation)
The ratio of the weight average molecular weight to the number average molecular weight obtained above was defined as the molecular weight distribution (Mw/Mn).
Examples 1 to 4 and comparative examples 1 to 4: production of colored photosensitive resin composition
The colored photosensitive resin compositions of examples 1 to 4 and comparative examples 1 to 4 were prepared with the following components and contents as shown in table 2.
[ Table 2]
Figure BDA0001500824370000141
Examples of the experiments
1. Evaluation of foreign matter
Colored layers were produced from the colored photosensitive resin compositions produced in examples 1 to 4 and comparative examples 1 to 4. That is, after coating on a glass substrate by spin coating, vacuum drying was performed for 17 seconds so that the degree of vacuum became 100Pa, thereby forming a thin film.
The thickness of the colored layer thus obtained was 2 μm. Then, the number of foreign substances generated in the 1cm × 1cm area was counted for the obtained substrate by an optical microscope, and the substrate was classified into the following three stages, and the results thereof are shown in table 3.
○ less than 5
△ more than 5 and less than 10
X: more than 10
Evaluation of VD streaking (stele streaks)
Colored layers were produced from the colored photosensitive resin compositions produced in examples 1 to 4 and comparative examples 1 to 4. That is, after coating on a glass substrate by a spin coating method, vacuum drying was performed for 17 seconds so that the degree of vacuum became 65Pa, and a thin film was formed.
The thickness of the colored layer thus obtained was 2 μm. Then, the number of VD streaks (stone streaks) generated in an area of 1cm × 1cm was counted by an optical microscope for the obtained substrate, and the substrate was classified in the following three stages, and the results thereof are shown in table 3.
○ less than 5
△ more than 5 and less than 10
X: more than 10
3. Evaluation of acicular (PIN) speckles
Colored layers were produced from the colored photosensitive resin compositions produced in examples 1 to 4 and comparative examples 1 to 4. That is, after coating on a glass substrate by spin coating, vacuum drying was performed for 17 seconds so that the degree of vacuum became 250Pa, and a thin film was formed. The thickness of the color filter thus obtained was 2 μm. Thereafter, the obtained substrate was baked on a hot plate (hotplate) provided with ceramic pins at 100 ℃ for 3 minutes, and the generated pin marks were visually recognized to have the following two-step zone definitions, and the results are shown in table 3.
○ not distinguishable by naked eyes
X: can be clearly distinguished by naked eyes
[ Table 3]
Foreign matter Stele pattern Needle-like speckle
Example 1 ○ ○ ○
Example 2 ○ ○ △
Example 3 ○ ○ ○
Example 4 ○ ○ ○
Comparative example 1 × △ ×
Comparative example 2 △ ○ ×
Comparative example 3 △ × ○
Comparative example 4 × ○ ×
As shown in Table 3, it is understood that examples 1 to 4 using a solvent having a boiling point of 170 degrees or more and a Hansen solubility parameter of 20 to 24 are superior to comparative examples 1 to 4 in foreign matter properties and favorable in stone-mark and needle-like stripe properties as a result of comparison of the compositions of the present invention.

Claims (7)

1. A pigment-dispersion composition comprising a colorant and a first solvent,
the colorant comprises c.i. pigment yellow 185,
the first solvent comprises Propylene Glycol Monomethyl Ether Acetate (PGMEA); and more than one substance with a boiling point of more than 170 ℃ and a Hansen solubility parameter of 20-24,
the substance having a boiling point of 170 ℃ or higher and a Hansen solubility parameter of 20-24 is selected from the group consisting of ethylene glycol butyl ether having a boiling point of 171 ℃ and a Hansen solubility parameter of 20.8, ethylene glycol phenyl ether having a boiling point of 247 ℃ and a Hansen solubility parameter of 23.5, ethylene glycol hexyl ether having a boiling point of 208 ℃ and a Hansen solubility parameter of 20.6, 3-methoxy-3-methyl-1-butanol having a boiling point of 175 ℃ and a Hansen solubility parameter of 20.2, propylene glycol phenyl ether having a boiling point of 241 ℃ and a Hansen solubility parameter of 21.5, dipropylene glycol methyl ether having a boiling point of 190 ℃ and a Hansen solubility parameter of 20, diethylene glycol methyl ether having a boiling point of 194 ℃ and a Hansen solubility parameter of 22, diethylene glycol ethyl ether having a boiling point of 202 ℃ and a Hansen solubility parameter of 22.2, diethylene glycol butyl ether having a boiling point of 230 ℃ and a Hansen solubility parameter of 20.4, triethylene glycol butyl ether having a boiling point of 249 ℃ and a Hansen solubility parameter of 20.7, At least one of triethylene glycol ethyl ether with a boiling point of 256 ℃ and a Hansen solubility parameter of 20.4.
2. A colored photosensitive resin composition comprising the pigment-dispersion composition according to claim 1, and further comprising one or more selected from the group consisting of an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, a second solvent, and an additive.
3. The colored photosensitive resin composition according to claim 2, wherein the alkali-soluble resin is contained in an amount of 10 to 80% by weight based on 100% by weight of the total solid content in the colored photosensitive resin composition containing the alkali-soluble resin.
4. The colored photosensitive resin composition according to claim 2, wherein the content of the photopolymerizable compound is 5 to 45% by weight based on 100% by weight of the total solid content in the colored photosensitive resin composition containing the photopolymerizable compound.
5. The colored photosensitive resin composition according to claim 2, wherein the content of the photopolymerization initiator is 0.1 to 40% by weight based on 100% by weight of the total solid content in the colored photosensitive resin composition containing the photopolymerization initiator.
6. A color filter comprising a cured product of the colored photosensitive resin composition according to any one of claims 2 to 5.
7. An image display device comprising the color filter according to claim 6.
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