CN108333871A - Photosensitive composition, colour filter and the display device comprising it - Google Patents
Photosensitive composition, colour filter and the display device comprising it Download PDFInfo
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- CN108333871A CN108333871A CN201711227588.4A CN201711227588A CN108333871A CN 108333871 A CN108333871 A CN 108333871A CN 201711227588 A CN201711227588 A CN 201711227588A CN 108333871 A CN108333871 A CN 108333871A
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- 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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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F212/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F212/02—Monomers containing only one unsaturated aliphatic radical
- C08F212/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F212/06—Hydrocarbons
- C08F212/12—Monomers containing a branched unsaturated aliphatic radical or a ring substituted by an alkyl radical
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
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- G—PHYSICS
- G02—OPTICS
- 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
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- 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
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- 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
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- 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
- G03F7/031—Organic compounds not covered by group G03F7/029
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Abstract
The present invention provides photosensitive composition, colour filter and the display device comprising it, the photosensitive composition is characterized in that, including colorant, alkali soluble resins, photopolymerizable compound, Photoepolymerizationinitiater initiater and solvent, above-mentioned colorant includes to be selected from one or more of C.I. naphthol greens 62 and C.I. naphthol greens 63 pigment, and above-mentioned Photoepolymerizationinitiater initiater includes oxime ester system Photoepolymerizationinitiater initiater.
Description
Technical field
The colour filter that is formed the present invention relates to photosensitive composition, by above-mentioned composition and comprising its display
Device.
Background technology
Colour filter is widely used in the various display devices such as photographing element, liquid crystal display device (LCD), and application range is just
It is expanding rapidly.The colour filter used in above-mentioned photographing element, liquid crystal display device etc. by red (Red), green (Green) and
The colored pattern of blue (Blue) this 3 kinds of colors is formed, or by yellow (Yellow), magenta (Magenta) and cyan
(Cyan) colored pattern of this 3 kinds of colors is formed.
Above-mentioned each colored pattern of colour filter, which generally utilizes, includes the colorants such as pigments or dyes, alkali soluble resins, photopolymerization
The photosensitive composition of property compound, Photoepolymerizationinitiater initiater and solvent is formed.Utilize above-mentioned coloring phototonus tree
The colored pattern processing of oil/fat composition is usually implemented by photo-mask process.
In recent years, for the various display devices comprising solid-state imager as digital camera, liquid crystal display device
(LCD) colour filter is used, in order to improve process and quality, it is desirable that there is high brightness and high coloring.
However, voltage retention is maintained certain level or more while the high brightness as maintenance and high coloring
Aspect has difficulties.Specifically, the 3 primary colors (red, green, blues as filter substrate；One of) RGB the body pigment of green,
In the case of using the halogenated phthalo-cyanines copper pigment such as C.I. pigment green 36s or C.I. pigment Green 7s, it is difficult to take into account high contrast and highlight
Degree.In addition, in order to solve these problems, in the case of using halogenated phthalo-cyanine zinc pigment, voltage retention is only 90% hereinafter, wanting
Asking improves it.
In addition, in order to solve the problems, such as that such voltage retention is bad, it is known that compound etc. of the addition containing epoxy group
Method (patent document 1), but exist occur caused by pigment type display it is uneven, be orientated it is bad the problems such as limitation.
Existing technical literature
Patent document
Patent document 1：Japanese Unexamined Patent Publication 2000-292920 bulletins
Invention content
Project to be solved
The present invention proposes to solve the problems, such as above-mentioned conventional art, it is intended that provide with high coloring power,
The photosensitive composition excellent in reliability such as the characteristic of high transmittance and high adhesion and solvent resistance.
In addition, it is therefore intended that, provide by have using above-mentioned photosensitive composition manufacture colour filter from
And voltage retention and the excellent display device of brightness.
The method to solve the problem
To achieve the goals above, the present invention provides a kind of photosensitive composition, which is characterized in that includes
Toner, alkali soluble resins, photopolymerizable compound, Photoepolymerizationinitiater initiater and solvent, above-mentioned colorant include to be selected from C.I. pigment
One or more of green 62 and C.I. naphthol greens 63 pigment, above-mentioned Photoepolymerizationinitiater initiater include oxime ester system Photoepolymerizationinitiater initiater.
In addition, the present invention provides the colour filter using the manufacture of above-mentioned photosensitive composition.
In addition, the present invention provides the display device for including above-mentioned colour filter.
Invention effect
The photosensitive composition of the present invention is capable of providing with the adaptation, transmitance, solvent resistance of base material etc.
The effect of excellent, the display device for having the colour filter formed using above-mentioned composition are capable of providing voltage retention and bright
Spend excellent effect.
Specific implementation mode
The present invention provides a kind of photosensitive composition, which is characterized in that comprising colorant, alkali soluble resins,
Photopolymerizable compound, Photoepolymerizationinitiater initiater and solvent, above-mentioned colorant include to be selected from C.I. naphthol greens 62 and C.I. naphthol greens
One or more of 63 pigment, above-mentioned Photoepolymerizationinitiater initiater include oxime ester system Photoepolymerizationinitiater initiater.
Hereinafter, each ingredient of the photosensitive composition for constituting the present invention illustrates.
(A) colorant
It is viridine green that colorant contained in the photosensitive composition of the present invention, which is aluminum phthalocyanine (Al-Ph),
It is characterized in that, comprising selected from as colour index (association of dyeing man will (The society of Dyers and
Colourists) publish) in be classified as pigment (pigment) compound C.I. naphthol greens 62 and C.I. naphthol greens 63 in
More than one pigment.The composition of the present invention includes selected from one or more of above-mentioned C.I. naphthol greens 62 and C.I. naphthol greens 63
In the case of pigment, high brightness can not only be provided, and is capable of providing the display device manufactured using the application composition
Voltage retention improvement.
Relative to colorant total weight, selected from one or more of above-mentioned C.I. naphthol greens 62 and C.I. naphthol greens 63 pigment
Content preferably can be 30~100 weight %.
The photosensitive composition of the present invention can further include yellow for the purpose of color adjustment or complementary color
Pigment.
Above-mentioned yellow uitramarine is specifically classified as pigment (pigment) in colour index (dyeing family association will publish)
Pigment compounds, preferably C.I. pigment yellows, specifically, the face illustrated with following colour index (C.I.) number can be used
Material, but it is not necessarily limited to this.
As the concrete example of above-mentioned C.I. pigment yellows, can enumerate C.I. pigment yellow 13s, 20,24,31,53,83,86,93,
94,109,110,117,125,129,137,138,139,147,148,150,153,154,166,173,180 and 185 etc.,
C.I. pigment Yellow 12s 9,138,139,150 and 185 etc. can be more preferably enumerated, they can be respectively individually or by two
Kind combination of the above uses.C.I. pigment yellow 13s 8 can further preferably be used.
, it is preferable to use the dispersible pigment dispersion of its uniform particle sizes dispersion in the case of using pigment as above-mentioned colorant.Make
For the method for the uniform particle sizes for making pigment, for example, addition pigment dispersing agent carries out the method etc. of decentralized processing,
According to this method, the dispersible pigment dispersion for the state that pigment is dispersed in solution can be obtained.As above-mentioned pigment dispersing agent,
For example, the surfactant etc. of cationic system, anionic system, nonionic system, both sexes system, Polyester, polyamine system etc.,
They can respectively individually or be use mixing two or more.
Above-mentioned pigment dispersing agent is unconfined can to use ability in order to which the solution of pigment is solidifying and maintains stability and adds
The substance generally used in domain.Preferably comprise includes BMA (butyl methacrylate) or DMAEMA (methacrylic acid N, N- diformazans
Base amino ethyl ester) acrylic ester dispersant (hereinafter referred to as acrylic dispersants).At this point, above-mentioned acrylic compounds dispersion
It is preferable to use according to activity (living) controlling party legal system as being disclosed in KR published patent 2004-0014311 for agent
The substance made can be enumerated as the commercially available product of the acrylic ester dispersant by above-mentioned active control method manufacture
DISPER BYK-2000, DISPER BYK-2001, DISPER BYK-2070, DISPER BYK-2150 etc..Above-mentioned acrylic acid
Ester system dispersant can respectively individually or be used in combination of two or more.
As above-mentioned pigment dispersing agent, other resin-bonded pigments other than acrylic ester dispersant can also be used to disperse
Agent.As other above-mentioned resin-bonded pigment dispersants, can enumerate well known resin-bonded pigment dispersant, especially polyurethane,
Using polyacrylate as the polycarboxylate of representative, unsaturated polyamide, polycarboxylic acids, (part) amine salt of polycarboxylic acids, polycarboxylic acids
Ammonium salt, the alkylamine salt of polycarboxylic acids, polysiloxanes, long-chain polyaminoamide phosphate, hydroxyl polycarboxylic acids ester and they
Modified product or with the freely polyester of (free) carboxyl and the amide for reacting and being formed of poly- (low-grade alkylidene imines) or
Oily dispersant as their salt；(methyl) acrylic-styrene copolymer, (methyl) acrylic acid-(methyl) acrylic acid
Water-soluble resin or water solubility as ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol or polyvinylpyrrolidone
Polymer compound；Polyester；Modified polyacrylate；The addition product of ethylene oxide/propylene oxide；With phosphate etc..Make
For the commercially available product of above-mentioned resin-bonded pigment dispersant, for cationic system pitch dispersant, it can be cited for example that BYK (finishes
Gram) trade name of chemical company：DISPER BYK-160、DISPER BYK-161、DISPER BYK-162、DISPER BYK-
163、DISPER BYK-164、DISPER BYK-166、DISPER BYK-171、DISPER BYK-182、DISPER BYK-
184；The trade name of BASF (BASF) company：EFKA-44、EFKA-46、EFKA-47、EFKA-48,EFKA-4010、EFKA-
4050、EFKA-4055、EFKA-4020、EFKA-4015、EFKA-4060、EFKA-4300、EFKA-4330、EFKA-4400、
EFKA-4406、EFKA-4510、EFKA-4800；Lubirzol (the trade names of (Lu Borun) company：SOLSPERS-24000、
SOLSPERS-32550、NBZ-4204/10；Grind the trade name for the company of refining in river：HINOACT T-6000、HINOACT T-
7000、HINOACT T-8000；The trade name of aginomoto company：AJISPUR PB-821、AJISPUR PB-822、AJISPUR
PB-823；The trade name of chemical company of common prosperity society：FLORENE DOPA-17HF、FLORENE DOPA-15BHF、FLORENE
DOPA-33, FLORENE DOPA-44 etc..Other resin-bonded pigment dispersants other than above-mentioned acrylic ester dispersant can be with
Respectively individually or be used in combination of two or more, can also be used in combination with acrylic ester dispersant.
100 parts by weight of solid constituent relative to used pigment are, it is preferable to use 5~60 weight of above-mentioned pigment dispersing agent
Part, more preferably use 15~50 parts by weight.In the case of being less than 5 parts by weight according to the content of said reference pigment dispersing agent, face
The problems such as gelation may occur after the micronized difficulty of material or dispersion.On the other hand, more than 60 parts by weight,
Viscosity may be got higher.
Relative to the feline amount in photosensitive composition, the content of above-mentioned colorant is preferably 5
~60 weight %, more preferably 10~45 weight %.In the case that the content of above-mentioned colorant is said reference, even if being formed thin
The color depth of film, pixel is also abundant, and the deciduous of non-pixel portion will not be reduced without generating residue when due to development, because
This is preferably.
(B) alkali soluble resins
Alkali soluble resins is the object used generally in the art contained in the photosensitive composition of the present invention
Matter, as long as then may be used for manufacturing the polymer that can be dissolved in the alkaline-based developer used in the development step of colour filter
To use with no particular limitation.
The alkaline developer utilized in development treatment process when in order to for forming pattern has solubility, above-mentioned alkali solubility
Resin preferably can include with carboxyl ethylene unsaturated monomer (b1) and be copolymerized manufactured, can also can with it is above-mentioned
The other monomers of monomer (b1) copolymerization are copolymerized and are manufactured.
As the concrete example of the above-mentioned ethylene unsaturated monomer (b1) with carboxyl, acrylic acid, methyl-prop can be enumerated
The monocarboxylic acids class such as olefin(e) acid, crotonic acid；The omega-dicarboxylic acids such as fumaric acid, mesaconic acid, itaconic acid；With the acid anhydrides of these dicarboxylic acids；ω-carboxylic
Base polycaprolactone list (methyl) acrylate etc. has list (methyl) acrylate of the polymer of carboxyl and hydroxyl in two ends
Class etc., preferably acrylic acid, methacrylic acid.
In order to assign hydroxyl to alkali soluble resins (B), above-mentioned alkali soluble resins can be by that will have the ethylene of carboxyl
Unsaturated monomer (b1) is copolymerized with the ethylene unsaturated monomer (b2) with hydroxyl and is manufactured, and can be shunk by making to have
Glyceryl compound (b3) is further reacted with the copolymer of the ethylene unsaturated monomer (b1) with carboxyl and is manufactured.This
It outside, can also the compound (b3) by making that there is glycidyl and ethylene unsaturated monomer (b1) and tool with carboxyl
There is the copolymer of the ethylene unsaturated monomer (b2) of hydroxyl further to react and manufacture.
As the concrete example of the above-mentioned compound (b3) with glycidyl, butyl glycidyl ether, contracting can be enumerated
Water glycerol propyl ether, phenyl glycidyl ether, 2- hexyl glycidyl ethers, Glycidyl butyrate, glycidol methyl
Ether, ethyl ether, glycidol isopropyl ether, tertiary butyl glycidyl ether, benzyl glycidyl ether, 4- tert-butyl benzenes
Formic acid ethylene oxidic ester, stearic acid glycidyl ester, arylolycidyl ethers, glycidyl methacrylate etc., more preferably
For butyl glycidyl ether, arylolycidyl ethers, glycidyl methacrylate, can be used in combination of two or more.
When manufacturing above-mentioned alkali soluble resins (B), the illustration of other copolymerizable unsaturated monomers (b4) is as follows, but and differs
Fixed limit schedules this.
As the concrete example of above-mentioned other copolymerizable unsaturated monomers (b4), can enumerate styrene, vinyltoluene,
α-methylstyrene, p-chlorostyrene, o-methoxystyrene, meta-methoxy styrene, to methoxy styrene, adjacent vinyl
Benzyl methyl ether, vinyl benzyl methyl ether, to vinyl benzyl methyl ether, adjacent vinylbenzyl glycidyl ether, second
Alkenyl benzyl glycidyl ether, to aromatic ethenyl compounds such as vinylbenzyl glycidyl ethers；
N- N-cyclohexylmaleimides, N- benzyl maleimides, N-phenylmaleimide, N- o-hydroxy-phenyls Malaysia
Hydroxyphenyl-maleimides between acid imide, N-, N- p-hydroxybenzenes maleimide, N- o-methyl-phenyls maleimide,
First between methylphenylmaleimide, N- p-methylphenyls maleimide, N- o-methoxyphenyls maleimide, N- between N-
The N- substituted maleimide amine compounds such as phenyl maleimide, N- p-methoxyphenyl maleimides；
(methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) n-propyl, (methyl) acrylic acid isopropyl
Ester, (methyl) n-butyl acrylate, (methyl) isobutyl acrylate, (methyl) sec-butyl acrylate, the tertiary fourth of (methyl) acrylic acid
Ester etc. (methyl) alkyl-acrylates；(methyl) acrylic acid ring pentyl ester, (methyl) cyclohexyl acrylate, (methyl) acrylic acid 2-
Methyl cyclohexyl, tricyclic [5.2.1.0 2,6] decane -8- bases (methyl) acrylate, bis- cyclopentyloxies of (methyl) acrylic acid 2-
Alicyclic (methyl) esters of acrylic acid such as ethyl ester, (methyl) isobornyl acrylate；
(methyl) acrylic acid 2- hydroxy methacrylates, (methyl) acrylic acid 2- hydroxy propyl esters, (methyl) acrylic acid 4- hydroxybutyls,
(methyl) the Hydroxyethyl Acrylate classes such as (methyl) acrylic acid 2- hydroxyl -3- phenoxy-propyls, N- hydroxyethyl acrylamides；
(methyl) the benzyl acrylate classes such as (methyl) phenyl acrylate, (methyl) benzyl acrylate；
3- (methacryloxymethyl) oxetanes, 3- (methacryloxymethyl) -3- ethyl oxa- rings
Butane, 3- (methacryloxymethyl) -2- trifluoromethyls oxetanes, 3- (methacryloxymethyl) -2- benzene
Base oxetanes, 2- (methacryloxymethyl) oxetanes, 2- (methacryloxymethyl) -4- fluoroforms
Unsaturation oxetane compound such as base oxetanes etc..
The monomer illustrated with above-mentioned (b4) can respectively individually or be used in combination of two or more.
In addition, in order to ensure the storage stability of compatibility and photosensitive composition with dyestuff, above-mentioned alkali
The acid value of soluble resin is preferably the range of 30~150mgKOH/g.It is less than the feelings of 30mgKOH/g in the acid value of alkali soluble resins
Under condition, photosensitive composition is difficult to ensure sufficient developing powder, more than 150mgKOH/g, exists
Following worry：Reduce and be easy to happen the short circuit of pattern with the adaptation of substrate, and goes wrong and make with the compatibility of dyestuff
Dyestuff in photosensitive composition is precipitated or the storage stability of composition reduces, and viscosity rises.
In addition, above-mentioned alkali soluble resins passes through gel permeation chromatography (GPC；Using tetrahydrofuran as eluting solvent) it surveys
Fixed polystyrene conversion weight average molecular weight (hereinafter referred to as weight average molecular weight) is 3,000~100,000, preferably 5,000
~50,000.The weight average molecular weight of above-mentioned alkali soluble resins within the above range in the case of, membrane left rate is high, non-exposed portion
Dissolubility is excellent in developer solution, and resolution ratio improves, thus preferably.
Relative to the feline amount in photosensitive composition, the content of above-mentioned alkali soluble resins is preferred
It can be 10~80 weight %, more preferably can be 10~70 weight %.It is 10~80 weights in the content of above-mentioned alkali soluble resins
In the case of measuring %, the dissolubility in developer solution is fully easy pattern and is formed, and prevents the film of exposure portion when development from reducing, non-
The deciduous of pixel portion becomes good, thus preferably.
(C) photopolymerizable compound
Photopolymerizable compound contained in the photosensitive composition of the present invention is to pass through aftermentioned photopolymerization
The effect of initiator and the compound that can polymerize can enumerate monofunctional monomer, two functional monomers and more officials as concrete example
Energy monomer etc..
As the concrete example of above-mentioned monofunctional monomer, nonylphenol acrylate phenyl carbitol ester, acrylic acid 2- hydroxyls can be enumerated
Base -3- phenoxy-propyls, acrylic acid 2- ethylhexyls carbitol ester, acrylic acid 2- hydroxy methacrylates and n-vinyl pyrrolidone
Deng but it is not limited to this.
As the concrete example of above-mentioned two functional monomer, 1,6- hexylene glycols two (methyl) acrylate, ethylene glycol can be enumerated
Pair of two (methyl) acrylate, neopentyl glycol two (methyl) acrylate, triethylene glycol two (methyl) acrylate, bisphenol-A
(acryloyl-oxyethyl) ether, 3- methyl pentanediols two (methyl) acrylate, butanediol dimethylacrylate, hexylene glycol two
(methyl) acrylate etc., but it is not limited to this.
As the concrete example of above-mentioned polyfunctional monomer, trimethylolpropane tris (methyl) acrylate, ethoxy can be enumerated
Base trimethylolpropane tris (methyl) acrylate, propoxylation trimethylolpropane tris (methyl) acrylate, Ji Wusi
Alcohol three (methyl) acrylate, pentaerythrite four (methyl) acrylate, dipentaerythritol five (methyl) acrylate, ethyoxyl
Change dipentaerythritol six (methyl) acrylate, (methyl) acrylate of propoxylated dipentaerythritol six and dipentaerythritol six
(methyl) acrylate etc., but it is not limited to this.
Relative to the feline amount in photosensitive composition, the content of above-mentioned photopolymerizable compound
More preferably can be 7~45 weight % it is preferred that can be 5~45 weight %.It is upper in the content of above-mentioned photopolymerizable compound
In the case of stating in range, the intensity and flatness of pixel portion become good, thus preferably.
(D) Photoepolymerizationinitiater initiater
Photoepolymerizationinitiater initiater contained in the photosensitive composition of the present invention includes that the photopolymerization of oxime ester system causes
Agent.Above-mentioned oxime ester system's Photoepolymerizationinitiater initiater shows effective photopolymerization since light efficiency is excellent under low light exposure
Characteristic.
As the concrete example of above-mentioned oxime ester system Photoepolymerizationinitiater initiater, 1,2- acetyl caproyls, 1- [4- (phenyl) can be enumerated
Phenyl]-, 2- (O- benzoyls oxime) (1,2-Octanedione, 1- [4- (phenylthio) phenyl]-, 2- (O-
Benzoyloxime)), 1- [9- ethyls -6- (2- methyl benzoyls) -9H- carbazole -3- bases] ethyl ketone -1- (O- acetyl oxime) (1-
[9-Ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone-1- (O-acetyloxime)) and 1-
[4- (phenyl) phenyl)] -3- cyclohexyl-propane -1,2- diketone -2- (O- acetyl oxime) (1- [4- (phenylthio)
Phenyl)] -3-cyclohexyl-propane-1,2-dione-2- (O-acetyloxime)) etc., preferably can use be selected from
1,2- acetyl caproyls, 1- [4- (phenyl) phenyl] -, 2- (O- benzoyls oxime) and 1- [9- ethyls -6- (2- toluyls
One or more of base) -9H- carbazole -3- bases] ethyl ketone -1- (O- acetyl oxime).In addition, as commercially available product, TRONLY can be enumerated
The PBG-327 of company, BASF AGOXE-01 (with reference to following chemical formula 1),OXE-02
(with reference to following chemical formula 2) andThe N-1919 etc. of OXE-03, Adeka company.
[chemical formula 1]
[chemical formula 2]
Above-mentioned oxime ester system Photoepolymerizationinitiater initiater can respectively individually or be used in combination of two or more.
Relative to Photoepolymerizationinitiater initiater total weight, the content of above-mentioned oxime ester system Photoepolymerizationinitiater initiater preferably can be 10~
100 weight % more preferably can be 20~100 weight %.Above-mentioned oxime ester system Photoepolymerizationinitiater initiater content according to above-mentioned base
Standard is easy hair less than that in the case of 10 weight %, can not solve the problems, such as that the sensitivity caused by colorant declines in developing procedure
The short circuit of raw pattern.
In addition, within the scope of the effect of the invention, as Photoepolymerizationinitiater initiater, in addition to the photopolymerization of oxime ester system is drawn
It sends out other than agent, composition of the invention can further include other Photoepolymerizationinitiater initiaters.Cause as other above-mentioned photopolymerization
The typical example of agent can enumerate acetophenone based compound, benzophenone based compound, triazine based compound, bisglyoxaline system chemical combination
Object and thioxanthones based compound etc. can use and be selected from one such above compound.
As the concrete example of above-mentioned acetophenone based compound, diethoxy acetophenone, 2- hydroxy-2-methyls-can be enumerated
1- phenyl-propane -1- ketone, benzil dimethyl ketal, 2- hydroxyls -1- [4- (2- hydroxyl-oxethyls) phenyl] -2- methylpropanes -
1- ketone, 1- hydroxycyclohexylphenylketones, 2- methyl-1s-(4- methylphenyl-sulfanyls) -2- morpholino propane -1- ketone, 2- benzyls -2- two
Methylamino -1- (4- morphlinophenyls) butane -1- ketone, 2- hydroxy-2-methyls -1- [4- (1- methyl ethylenes) phenyl] third
Alkane -1- ketone and 2- (4- methylbenzyls) -2- (dimethylamino) -1- (4- morphlinophenyls) butane -1- ketone etc..
As the concrete example of above-mentioned benzophenone based compound, can enumerate benzophenone, methyl o-benzoylbenzoate,
4- phenyl benzophenones, 4- benzoyl -4'- dimethyl diphenyl sulfides, 3,3', 4,4'- tetra- (tert-butyl hydroperoxide carbonyl) hexichol
Ketone and 2,4,6- tri-methyl benzophenones etc..
As the concrete example of above-mentioned triazine based compound, bis- (trichloromethyl) -6- (the 4- methoxybenzenes of 2,4- can be enumerated
Base) -1,3,5- triazines, 2,4- bis- (trichloromethyl) -6- (4- methoxyl groups naphthalene) -1,3,5- triazines, 2,4- bis- (trichloromethyls) -
Bis- (trichloromethyl) -6- (4- the methoxyl-styrenes) -1,3,5- triazines of 6- piperonyl -1,3,5- triazines, 2,4-, 2,4- are bis-
(trichloromethyl) -6- [2- (5- methylfuran -2- bases) vinyl] -1,3,5- triazines, bis- (trichloromethyl) -6- [2- (furans of 2,4-
Mutter -2- bases) vinyl] -1,3,5- triazines, bis- (the trichloromethyl) -6- of 2,4- [2- (4- diethylamino -2- aminomethyl phenyls) second
Alkenyl] -1,3,5- triazines and bis- (the trichloromethyl) -6- of 2,4- [2- (3,4- Dimethoxyphenyls) vinyl] -1,3,5- triazines
Deng.
As the concrete example of above-mentioned bisglyoxaline based compound, 2,2'- bis- (2- chlorphenyls) -4,4', 5,5'- tetra- can be enumerated
Phenyl bisglyoxaline, 2,2'- bis- (2,3- dichlorophenyls) -4,4', 5,5'- tetraphenyls bisglyoxaline, 2,2'- bis- (2- chlorphenyls) -4,
4', 5,5'- tetra- (alkoxyl phenyl) bisglyoxaline, 2,2'- bis- (2- chlorphenyls) -4,4', 5,5'- tetra- (tri-alkoxy phenyl) join miaow
Bis- (2,6- dichlorophenyls) -4,4', the 5,5'- tetraphenyl -1,2'- bisglyoxalines of azoles, 2,2- or 4,4', 5,5' phenyl are by alcoxyl
The imidazolium compounds etc. of carbonyl (carboalkoxy) substitution.Wherein, 2,2'- bis- (2- chlorphenyls) -4,4' can be preferably used,
5,5'- tetraphenyls bisglyoxaline, 2,2'- bis- (2,3- dichlorophenyls) -4,4', the bis- (2,6- bis- of 5,5'- tetraphenyls bisglyoxaline, 2,2-
Chlorphenyl) -4,4', 5,5'- tetraphenyl -1,2'- bisglyoxalines.
As the concrete example of above-mentioned thioxanthones based compound, 2-isopropylthioxanthone, 2,4- diethyl thioxanthenes can be enumerated
Ketone, bis- clopenthixal ketones of 2,4- and the chloro- 4- propoxythioxanthones of 1- etc..
Above-mentioned Photoepolymerizationinitiater initiater can also be used in combination with photopolymerization initiator.The composition of the present invention further includes
In the case of stating photopolymerization initiator, sensitivity becomes higher and productivity can be made to improve.Cause as above-mentioned photopolymerization
The concrete example of auxiliary agent can enumerate amine compound, carboxylic acid compound etc., and but it is not limited to this.
As above-mentioned amine compound, aromatic amines compound can be more preferably used.As above-mentioned amine compound
Concrete example can enumerate the aliphatic amine compounds such as triethanolamine, methyl diethanolamine, triisopropanolamine；4- dimethylaminos
Methyl benzoate, ethyl 4-dimethylaminobenzoate, 4- dimethylaminobenzoic acids isopentyl ester, 4- dimethylaminobenzoic acids
2- ethylhexyls, benzoic acid 2- dimethylamino ethyl esters, N, bis- (dimethylamino) hexichol of N- dimethyl-p-toluidines, 4,4'-
Ketone (common name：Michler's keton), bis- (diethylamino) benzophenone of 4,4'- etc..
Above-mentioned carboxylic acid compound more preferably can be the miscellaneous acetic acid class of aromatic series.As the concrete example of above-mentioned carboxylic acid compound,
It can be cited for example that phenyl acetic acid, aminomethyl phenyl thioacetic acid, ethylphenyl thioacetic acid, the thio second of Methylethyl phenyl
Acid, 3,5-dimethylphenyl thioacetic acid, methoxyphenylthio acetic acid, dimethoxyphenylthio acetic acid, chlorophenylthio acetic acid,
Dichlorophenyl thioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthio acetic acid, N- naphthalenes glycine, naphthoxy acetic acid
Deng.
Above-mentioned photopolymerization initiator can respectively individually or be use mixing two or more.
On the basis of the feline amount in the photosensitive composition of the present invention, above-mentioned photopolymerization causes
The content of auxiliary agent preferably can be 5~40 weight %, more preferably can be 10~30 weight %.
In the case where the content of above-mentioned photopolymerization initiator is in above-mentioned content range, coloring phototonus resin group
Closing the sensitivity of object becomes better, and the productivity of the colour filter formed using the composition is improved, thus preferably.
Relative to the feline amount in photosensitive composition, the content of above-mentioned Photoepolymerizationinitiater initiater is excellent
It is selected as 5~40 weight %, more preferably 5~15 weight %.The feelings of the content of above-mentioned Photoepolymerizationinitiater initiater within the above range
Under condition, photosensitive composition makes the time for exposure shorten by high-sensitivity, can improve productivity and remain high
Resolution ratio, thus preferably.
(E) solvent
As long as solvent makes photosensitive composition contained in the photosensitive composition of the present invention
Contained in other compositions dissolving when effectively can then use solvent usually used in this field without particular limitation.
As above-mentioned solvent, ethers, acetate esters, aromatic hydrocarbon, ketone, alcohols, esters or amides can be used
Solvent etc. can more preferably use acetate esters solvents.
As above-mentioned ether solvent, specifically, ethylene glycol single methyl ether, ethylene glycol monomethyl ether, second two can be enumerated
The ethylene glycol monoalkyl ethers class such as alcohol list propyl ether and ethylene glycol monobutyl ether；
Diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether and diethylene glycol dibutyl ether
Etc. diethylene glycol dialkyl ethers class etc..
As above-mentioned acetate esters solvents, specifically, methylcellosolve acetate and ethyl cellosolve second can be enumerated
The ethylene glycol alkyl ethers acetate esters such as acid esters；
Propylene glycol monomethyl ether, propylene glycol monoethyl acetic acid esters, propylene glycol monopropyl ether acetic acid esters, methoxyl group
Aklylene glycols alkylether acetates class such as butylacetic acid ester and methoxypentyl acetic acid esters etc..
As above-mentioned aromatic hydrocarbon solvent, specifically, benzene,toluene,xylene and mesitylene etc. can be enumerated.
As above-mentioned ketones solvent, specifically, methyl ethyl ketone, acetone, methyl amyl ketone, methyl tert-butyl can be enumerated
Base ketone and cyclohexanone etc..
As above-mentioned alcohols solvent, specifically, can enumerate ethyl alcohol, propyl alcohol, butanol, hexanol, cyclohexanol, ethylene glycol and
Glycerine etc..
As above-mentioned esters solvent, specifically, can enumerate 3- ethoxyl ethyl propionates and 3- methoxy methyl propionates,
And cyclic annular esters such as gamma-butyrolacton etc..
As above-mentioned amide solvent, specifically, n,N-Dimethylformamide, n,N-dimethylacetamide can be enumerated
With N-Methyl pyrrolidone etc..
From the aspect of coating and drying property, the organic solvent that the above-mentioned preferred boiling point of solvent is 100~200 DEG C is more excellent
Choosing can be used selected from propylene glycol monomethyl ether, propylene glycol monoethyl acetic acid esters, cyclohexanone, ethyl lactate, lactic acid
One or more of butyl ester, 3- ethoxyl ethyl propionates and 3- methoxy methyl propionates etc..
As one embodiment of the invention, above-mentioned solvent is preferably propylene glycol monomethyl ether, total relative to solvent
The content of weight, methyl proxitol acetate is preferably 20~100 weight %.Content within the above range the case where
Under, it can be ensured that the viscosity stability of photosensitive composition, thus preferably.
Relative to the photosensitive composition total weight of the present invention, the content of above-mentioned solvent can be 60~90 weights
% is measured, more preferably can be 70~85 weight %.In the case of being 60~90 weight % according to the content of said reference solvent, make
It is applied with apparatus for coating such as roll coater, spin coater, slit spin coater, slit coater (sometimes referred to as die coating machine), ink jet printers
When cloth, providing makes coating become good effect, thus preferably.
Other than mentioned component, in the range of not damaging the purpose of the present invention, according to the need of those skilled in the art
It wants, coloring photosensitive combination of the invention can also further include other additives.
Above-mentioned additive can be added selectively as needed, it can be cited for example that curing agent, surfactant, closely sealed
Accelerating agent, antioxidant, ultra-violet absorber or anticoagulant etc..
Above-mentioned curing agent is used to realize deeply-curing and improve mechanical strength, as concrete example, can be enumerated
Epoxide, polyfunctional isocyanate compound, melamine compound and oxetane compound etc..
In above-mentioned curing agent, as the concrete example of epoxide, bisphenol A type epoxy resin, hydrogenated bisphenol A can be enumerated
Type epoxy resin, bisphenol f type epoxy resin, A Hydrogenated Bisphenol A F types epoxy resin, phenolic resin varnish type epoxy resin, other aromatic series
It is epoxy resin, alicyclic ring family epoxy resin, ethylene oxidic ester system resin, glycidol amine system resin or above-mentioned epoxy resin
Brominated derivative, the aliphatic other than epoxy resin and its brominated derivative, alicyclic or aromatic epoxy compound, fourth two
Alkene (co) polymer epoxides, isoprene (co) polymer epoxides, (methyl) glycidyl acrylate are (total) poly-
Close object, triglycidyl isocyanurate etc..
In above-mentioned curing agent, as the concrete example of oxetane compound, can enumerate carbonic ester dioxygen azetidine,
Dimethylbenzene dioxygen azetidine, adipate ester dioxygen azetidine, terephthalate dioxygen azetidine, cyclohexane dicarboxylic acid
Dioxygen azetidine etc..
Above-mentioned curing agent can be used in combination with curing compound is helped, described to help curing compound that make epoxy together with curing agent
The epoxy group of compound, the oxetanes scaffolds open polymerization of oxetane compound.It is above-mentioned to help curing compound for example
There are polybasic carboxylic acid class, polybasic carboxylic acid anhydride, acid agent etc..Above-mentioned polybasic carboxylic acid anhydride can utilize commercially available epoxy resin cure
Agent.About the concrete example of above-mentioned epoxy curing agent, trade name (the ADEKA HARDENER as commercially available product can be enumerated
EH-700) (ADEKA industry (strain) manufacture), trade name (RIKACID HH) (new Japan Chemical (strain) manufacture), trade name (MH-
700) (new Japan Chemical (strain) manufacture) etc..Foregoing illustrative curing agent can be independent or be use mixing two or more.
Above-mentioned surfactant can use to further increase the envelope formative of photosensitive polymer combination, excellent
Choosing can use silicone based surfactants or fluorine system surfactant etc..
Above-mentioned silicone based surfactants are for example, DOW CORNING Dong Li organosilicons company as commercially available product
DC3PA, DC7PA, SH11PA, SH21PA and SH8400 etc., TSF-4440, TSF-4300, TSF- of organosilicon company of GE Toshiba
4445, TSF-4446, TSF-4460 and TSF-4452 etc..Above-mentioned fluorine system surfactant is for example, as commercially available product
Megafac F-470, F-471, F-475, F-482 and F-489 etc. of Japanese ink chemical industrial company greatly.Foregoing illustrative table
Face activating agent can respectively individually or be used in combination of two or more.
As the concrete example of above-mentioned closely sealed accelerating agent, vinyltrimethoxysilane, vinyl triethoxyl can be enumerated
Silane, vinyl three (2- methoxy ethoxies) silane, N- (2- amino-ethyls) -3- aminopropylmethyldimethoxysilanes,
N- (2- amino-ethyls) -3- TSL 8330s, 3-aminopropyltriethoxysilane, 3- glycidoxypropyl groups
Trimethoxy silane, 3- glycidoxypropyls dimethoxysilane, 2- (3,4- expoxycyclohexyls) ethyl trimethoxy
Base silane, 3- chloropropylmethyldimethoxysilanes, 3- r-chloropropyl trimethoxyl silanes, 3- methacryloxypropyl front threes
Oxysilane, 3-mercaptopropyi trimethoxy silane, 3- isocyanate group propyl trimethoxy silicane and 3- isocyanate group third
Ethyl triethoxy silicane alkane etc..Foregoing illustrative closely sealed accelerating agent can respectively individually or be use mixing two or more.
As the concrete example of above-mentioned antioxidant, 2,2'- thiobis (4- methyl-6-tert-butylphenols) and 2 can be enumerated,
6- di-tert-butyl-4-methy phenols etc..
As the concrete example of above-mentioned ultra-violet absorber, 2- (3- tertiary butyl -2- hydroxy-5-methyl base benzene can be enumerated
Base) -5- chlorobenzotriazoles and alkoxy benzophenone etc..
As the concrete example of above-mentioned anticoagulant, Sodium Polyacrylate etc. can be enumerated.
Relative to the feline amount of photosensitive composition, the content of above-mentioned additive is typically
0.01~10 weight % preferably can be 0.05~3 weight %.
The photosensitive composition of the present invention for example sharp can with the following method manufacture.
First, pigment is mixed in above-mentioned colorant with solvent, the average grain diameter of pigment is dispersed to using ball mill etc.
For 0.2 μm or less degree.At this point, as needed, part or all and solvent of pigment dispersing agent, alkali soluble resins can be made
It is mixed together, is dissolved or is disperseed.
In the dispersion liquid of above-mentioned mixing, colorant, residue can be further added in a manner of reaching scheduled concentration
Alkali soluble resins, photopolymerizable compound and Photoepolymerizationinitiater initiater and additive and solvent as needed, to manufacture this
The photosensitive composition of invention.
<Colour filter>
In order to realize that another object of the present invention, the present invention provide a kind of colour filter, which is characterized in that be included on substrate
Be exposed in a predetermined pattern after being coated with the photosensitive composition of the present invention and develop and the color layer that is formed.
The colour filter of the present invention includes the photosensitive composition system by the present invention on substrate and aforesaid substrate
The colored pattern made.Aforesaid substrate can be used as transparent material has sufficient intensity and branch for the stability of colour filter
The material of load.It is preferred that the glass that chemical stability is excellent, intensity is high can be used, but it is not limited to this.
That is, the present invention provides the colour filter of the colored pattern comprising the photosensitive composition manufacture by the present invention
The manufacturing method of device, above-mentioned colour filter can utilize conventional method as known in the art.
<Display device>
In addition, the present invention provides the display device for including above-mentioned colour filter.Above-mentioned display device is in addition to having above-mentioned hair
Except bright colour filter, including composition well known by persons skilled in the art in the technical field of the present invention, that is, the present invention includes energy
The display device of the colour filter of enough application present invention.Above-mentioned display device can be liquid crystal display device, transmission-type or reflection-type
Color liquid crystal display device, colour pick-up tube element or organic EL display element, electronic clock etc., but it is not limited to this.
Hereinafter, the present invention is described in more detail using embodiment and comparative example.But following embodiments are for illustrating this hair
Bright, the present invention is not limited by following embodiments and comparative example, can carry out various amendments and change within the scope of the invention.
The scope of the present invention is determined by the technological thought of appended claims.
<Synthesis example>
The synthesis (B-1) of 1. alkali soluble resins of synthesis example
In the flask for having blender, thermometer, reflux condensing tube, dropping funel and nitrogen ingress pipe, input the third two
120 parts by weight of alcohol monomethyl ether acetate, 80 parts by weight of propylene glycol monomethyl ether, azodiisobutyronitrile
(Azobisisobutyronitrile, AIBN) 2 parts by weight, 13 parts by weight of acrylic acid, 10 parts by weight of benzyl methacrylate, 4-
57 parts by weight of methyl styrene, 20 parts by weight of methyl methacrylate, 3 parts by weight of n-dodecyl mercaptan, and carry out nitrogen and set
It changes.Later, the temperature of reaction solution is risen to 110 DEG C while stirring, and reacted 6 hours.The alkali soluble resins synthesized in this way
Solid constituent acid value be 100.2mgKOH/g, by GPC measure weight average molecular weight Mw be about 15,110.
<Production Example>The manufacture of pigment dispensing composition
<Pigment dispensing composition M1>
Using ball mill, by as 62 12.0 parts by weight of C.I. naphthol greens of pigment, as the LPN- of pigment dispersing agent
6919 (manufacture of Bi Ke (BYK) company) 4 parts by weight, 84 parts by weight mixing of methyl proxitol acetate/dispersion as solvent
12 hours, to the dispersion liquid M1 that makes paints.
<Pigment dispensing composition M2>
Using ball mill, by as 63 12 parts by weight of C.I. naphthol greens of pigment, as the LPN-6919 of pigment dispersing agent
(manufacture of Bi Ke companies) 4 parts by weight mix/disperse 12 hours as 84 parts by weight of methyl proxitol acetate of solvent, from
And the dispersion liquid M2 that makes paints.
<Pigment dispensing composition M3>
Using ball mill, by as 12 parts by weight of C.I. pigment Green 7s of pigment, as the LPN-6919 of pigment dispersing agent
(manufacture of Bi Ke companies) 4 parts by weight mix/disperse 12 hours as 84 parts by weight of methyl proxitol acetate of solvent, from
And the dispersion liquid M3 that makes paints.
<Pigment dispensing composition M4>
Using ball mill, by as 58 12 parts by weight of C.I. naphthol greens of pigment, as the LPN-6919 of pigment dispersing agent
(manufacture of Bi Ke companies) 4 parts by weight mix/disperse 12 hours as 84 parts by weight of methyl proxitol acetate of solvent, from
And the dispersion liquid M4 that makes paints.
<Pigment dispensing composition M5>
Using ball mill, by as 8 12 parts by weight of C.I. pigment yellow 13s of pigment, as the LPN- of pigment dispersing agent
6919 (manufacture of Bi Ke companies) 4 parts by weight, as solvent 84 parts by weight of methyl proxitol acetate mix/to disperse 12 small
When, to the dispersion liquid M5 that makes paints.
<Embodiment and comparative example>The manufacture of photosensitive composition
Embodiment 1.
It will be above-mentioned<Pigment dispensing composition M1>15.43 parts by weight,<Pigment dispensing composition M5>12.50 parts by weight,<It closes
At example 1>12.47 parts by weight of resin, KAYARAD DPHA (Japanese chemical drug manufacture) 4.64 parts by weight,OXE-02
(BASF AG's manufacture) 1.40 parts by weight, the mixing of 53.56 parts by weight of propylene glycol monomethyl ether, manufacture coloring phototonus
Resin combination.
Embodiment 2.
It will be above-mentioned<Pigment dispensing composition M2>15.43 parts by weight,<Pigment dispensing composition M5>12.50 parts by weight,<It closes
At example 1>12.47 parts by weight of resin, KAYARAD DPHA (Japanese chemical drug manufacture) 4.64 parts by weight,OXE-02
(BASF AG's manufacture) 1.40 parts by weight, the mixing of 53.56 parts by weight of propylene glycol monomethyl ether, manufacture coloring phototonus
Resin combination.
Embodiment 3.
It will be above-mentioned<Pigment dispensing composition M2>15.43 parts by weight,<Pigment dispensing composition M5>12.50 parts by weight,<It closes
At example 1>12.47 parts by weight of resin, KAYARAD DPHA (Japanese chemical drug manufacture) 4.64 parts by weight,OXE-01
(BASF AG's manufacture) 1.40 parts by weight, the mixing of 53.56 parts by weight of propylene glycol monomethyl ether, manufacture coloring phototonus
Resin combination.
Embodiment 4.
It will be above-mentioned<Pigment dispensing composition M2>30.86 parts by weight,<Synthesis example 1>13.00 parts by weight of resin,
KAYARAD DPHA (Japanese chemical drug manufacture) 4.66 parts by weight,OXE-01 (BASF AG's manufacture) 1.40 weight
Part, the mixing of 50.08 parts by weight of propylene glycol monomethyl ether, manufacture photosensitive composition.
Comparative example 1.
It will be above-mentioned<Pigment dispensing composition M1>15.43 parts by weight,<Pigment dispensing composition M5>12.50 parts by weight,<It closes
At example 1>12.48 parts by weight of resin, KAYARAD DPHA (Japanese chemical drug manufacture) 4.64 parts by weight,369 (bar
Si Fu companies manufacture) 1.40 parts by weight, 53.56 parts by weight of propylene glycol monomethyl ether mixing, manufacture coloring phototonus tree
Oil/fat composition.
Comparative example 2.
It will be above-mentioned<Pigment dispensing composition M3>15.43 parts by weight,<Pigment dispensing composition M5>12.50 parts by weight,<It closes
At example 1>12.48 parts by weight of resin, KAYARAD DPHA (Japanese chemical drug manufacture) 4.64 parts by weight,OXE-02
(BASF AG's manufacture) 1.40 parts by weight, the mixing of 53.56 parts by weight of propylene glycol monomethyl ether, manufacture coloring phototonus
Resin combination.
Comparative example 3.
It will be above-mentioned<Pigment dispensing composition M4>15.43 parts by weight,<Pigment dispensing composition M5>12.50 parts by weight,<It closes
At example 1>12.48 parts by weight of resin, KAYARAD DPHA (Japanese chemical drug manufacture) 4.64 parts by weight,OXE-02
(BASF AG's manufacture) 1.40 parts by weight, the mixing of 53.56 parts by weight of propylene glycol monomethyl ether, manufacture coloring phototonus
Resin combination,
<Experimental example>
Using the photosensitive composition manufactured in above-described embodiment 1~4 and comparative example 1~3, following manufacture filter
Color device, and profit evaluates adaptation, transmitance, voltage retention and solvent resistance at this time with the following method, its result is shown
In table 1.
<Production Example>The manufacture of colour filter
Using the photosensitive composition manufactured in above-described embodiment 1~4 and comparative example 1~3, following manufacture filter
Color device.
The photosensitive composition of manufacture is coated on to the glass substrate (# of 5cm x 5cm using spin-coating method
1737, Corning Incorporated's manufacture) on, it is then placed in heating plate, is maintained 3 minutes in 100 DEG C of temperature and form film.It connects
It, places the photomask of the pattern with 3x3 on the above-mentioned films, and the interval with photomask is set as 300 μm and is irradiated purple
Outside line.At this point, ultraviolet light source has used the high-pressure mercury-vapor lamp of the 1kW comprising g, h, i ray this three, with 40mJ/cm2Photograph
Degree irradiation, and without using special optical filter.
The film of above-mentioned illuminated ultraviolet light is impregnated 2 minutes in the KOH aqueous development solution of pH 10.5 and is carried out
Development.It is dried using distilled water, after washing is coated with the glass substrate of above-mentioned film, nitrogen blowing, and is dried in 230 DEG C of heating
It is heated 25 minutes in case, manufactures colour filter.Pattern form (film) film thickness of the colour filter of manufacture is 2.3 μm.
1. adaptation of experimental example is evaluated
After the sheet material of making is cut in the region of 10 × 10mm with 100 matrix structures, jointing tape on it, really
Recognize the number for the matrix that the when of vertically firmly demoulding falls off.
<Adaptation evaluation criteria>
○：It is not peeled off on pattern
△：1~4 is peeled off on pattern
×：5 or more are peeled off on pattern
2. transmitance of experimental example is evaluated
It is and above-mentioned other than not using experiment photomask about transmitance<The making of colour filter>Similarly make filter
Color device is measured using colorimeter (Olympus Corp manufactures, OSP-200).
<Transmitance evaluation criteria>
◎：Brightness value is more than 53
○：Brightness value is 50~53
×：Brightness value is less than 50
Experimental example 3.VHR evaluations
Measure the voltage retention (VHR) of the colour filter of above-mentioned manufacture.VHR boxes (VHR cell) making and determination condition are such as
Under.
The filter substrate of above-mentioned manufacture is scraped into (scratch) and is obtained with powder (powder) shape.
Resist (Resist):Liquid crystal (LC)=1:After 97 mixing, (aging) is cured at 60 DEG C 20 hours.It is measured to VHR
After the inboard input isopropanol (IPA) of box, 30 minutes ultrasonic cleanings are carried out at 35 DEG C.By LC after curing and resist
Mixture carry out 0.2um syringe filterings, in the LC input boxes that filtering (filtering) is obtained afterwards.East is utilized after soldering
Foreign company (Toyo companies) VHR sensing equipments measure VHR with following condition, record its result in following table 1.
[60 DEG C of VHR determination conditions apply voltage 1V-100ms]
<Voltage retention evaluation criteria>
It is very good：Voltage retention is 95% or more
It is outstanding：Voltage retention is 90% less than 95%
Commonly：Voltage retention is 85% less than 90%
It is bad：Voltage retention is less than 85%
4. solvent resistance of experimental example is evaluated
Substrate is made in the same manner as above-mentioned experimental example 2, for the chromaticity coordinates for the substrate that the measurement of coloration and transmitance terminates,
It is measured using colorimeter (Olympus Corp manufactures, OSP-200).The substrate that the measurement of chromaticity coordinates is terminated is at 90 DEG C
It is impregnated 2 minutes in N-Methyl pyrrolidone.It after substrate is taken out, is washed with distilled water, measures coloration again, according to following mathematics
Formula 1 calculates and impregnates front and back aberration in N-Methyl pyrrolidone, and evaluated according to following benchmark.
It may determine that smaller for value of chromatism, can more manufacture the high colour filter of reliability.
<Mathematical expression 1>
Chromaticity coordinates (L after being impregnated in L*a*b* coordinate systems2 *, a2 *, b2 *), chromaticity coordinates (L before impregnating1 *, a1 *, b1 *)
<Solvent resistance evaluation criteria>
○：Δ E*ab is 3.0 or less
△：Δ E*ab is more than 3.0 and is 5.0 or less
×：Δ E*ab is more than 5.0
[table 1]
It can be confirmed by the result of above-mentioned table 1, it is closely sealed using the Examples 1 to 4 of the application composition
Property, transmitance, voltage retention and solvent resistance evaluation it is excellent.
On the other hand, in the case of comparative example 1 not comprising oxime ester system Photoepolymerizationinitiater initiater, transmitance and solvent resistance
It is bad, in the case where having used comparative example 2 of C.I. pigment Green 7 pigment, voltage retention, adaptation, transmitance and resistance to molten
Agent evaluation is bad.
In addition it confirms, in the case where having used comparative example 3 of 58 pigment of C.I. naphthol greens, voltage retention and resistance to molten
Agent is bad.
Claims (10)
1. a kind of photosensitive composition, which is characterized in that
Including colorant, alkali soluble resins, photopolymerizable compound, Photoepolymerizationinitiater initiater and solvent,
The colorant includes to be selected from one or more of C.I. naphthol greens 62 and C.I. naphthol greens 63 pigment,
The Photoepolymerizationinitiater initiater includes oxime ester system Photoepolymerizationinitiater initiater.
2. photosensitive composition according to claim 1, which is characterized in that
Relative to the feline amount in composition, including：
5~60 weight % of colorant,
10~80 weight % of alkali soluble resins,
5~45 weight % of photopolymerizable compound and
5~40 weight % of Photoepolymerizationinitiater initiater.
3. photosensitive composition according to claim 1, which is characterized in that
Relative to composition total weight, including 60~90 weight % of the solvent.
4. photosensitive composition according to claim 1, which is characterized in that
Relative to Photoepolymerizationinitiater initiater total weight, including 10~100 weight % of oxime ester system Photoepolymerizationinitiater initiater.
5. photosensitive composition according to claim 1, which is characterized in that
Oxime ester system Photoepolymerizationinitiater initiater includes to be selected from 1,2- acetyl caproyls, 1- [4- (phenyl) phenyl]-, 2- (O- benzene first
Acyl oxime), 1- [9- ethyls -6- (2- methyl benzoyls) -9H- carbazole -3- bases] ethyl ketone -1- (O- acetyl oxime) and 1- [4- (phenyl
One or more of it is thio) phenyl)] -3- cyclohexyl-propane -1,2- diketone -2- (O- acetyl oxime).
6. photosensitive composition according to claim 1, which is characterized in that
Oxime ester system Photoepolymerizationinitiater initiater includes to be selected from 1,2- acetyl caproyls, 1- [4- (phenyl) phenyl]-, 2- (O- benzene first
Acyl oxime) and 1- [9- ethyls -6- (2- methyl benzoyls) -9H- carbazole -3- bases] ethyl ketone -1- (O- acetyl oxime) in it is a kind of with
On.
7. photosensitive composition according to claim 1, which is characterized in that
The acid value of the alkali soluble resins is 30~150mgKOH/g.
8. photosensitive composition according to claim 1, which is characterized in that
Relative to the colorant total weight, including being selected from one or more of C.I. naphthol greens 62 and C.I. naphthol greens 63 pigment
30~100 weight %.
9. a kind of colour filter is manufactured using the photosensitive composition described in any one of claim 1~8.
10. a kind of display device, it includes the colour filters of claim 9.
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| KR1020170009622A KR102498590B1 (en) | 2017-01-20 | 2017-01-20 | Colored photosensitive resin composition, color filter and display device having the same |
| KR10-2017-0009622 | 2017-01-20 |
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| WO2020241328A1 (en) * | 2019-05-29 | 2020-12-03 | 株式会社Ｄｎｐファインケミカル | Photosensitive colored resin composition for color filter, cured object, color filter, and display device |
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| KR102353829B1 (en) * | 2019-03-12 | 2022-01-24 | 동우 화인켐 주식회사 | Colored photo sensitive resin composition, a color filter comprising the same, and an image display devide comprising the color filter |
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| CN106909027A (en) * | 2015-12-23 | 2017-06-30 | 东友精细化工有限公司 | Photosensitive composition, colour filter and its preparation method, image display device |
| CN109564384A (en) * | 2016-08-01 | 2019-04-02 | 东洋油墨Sc控股株式会社 | Photosensitive coloring composition and colored filter |
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| JP2000292920A (en) | 1999-04-02 | 2000-10-20 | Jsr Corp | Radiation sensitive composition for color filter |
| JP5030375B2 (en) | 2004-09-29 | 2012-09-19 | 富士フイルム株式会社 | Photocurable composition for color filter, solid-state imaging device and cyan color filter |
| KR20100021360A (en) | 2008-08-15 | 2010-02-24 | 후지필름 가부시키가이샤 | Organic electro-luminescence display |
| KR101987657B1 (en) * | 2013-03-28 | 2019-06-12 | 동우 화인켐 주식회사 | Colored photosensitive resin composition |
| KR102241498B1 (en) * | 2015-03-25 | 2021-04-16 | 동우 화인켐 주식회사 | Colored photosensitive resin composition for red or green pixel |
| KR102497605B1 (en) * | 2015-12-23 | 2023-02-08 | 동우 화인켐 주식회사 | Colored photosensitive resin composition, color filter, image display device, and method for manufacturing the color filter |
| WO2018025806A1 (en) * | 2016-08-01 | 2018-02-08 | 東洋インキＳｃホールディングス株式会社 | Photosensitive coloring composition and color filter |
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| CN106909027A (en) * | 2015-12-23 | 2017-06-30 | 东友精细化工有限公司 | Photosensitive composition, colour filter and its preparation method, image display device |
| CN109564384A (en) * | 2016-08-01 | 2019-04-02 | 东洋油墨Sc控股株式会社 | Photosensitive coloring composition and colored filter |
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| WO2020241328A1 (en) * | 2019-05-29 | 2020-12-03 | 株式会社Ｄｎｐファインケミカル | Photosensitive colored resin composition for color filter, cured object, color filter, and display device |
| JP6817503B1 (en) * | 2019-05-29 | 2021-01-20 | 株式会社Ｄｎｐファインケミカル | Photosensitive colored resin compositions for color filters, cured products, color filters, and display devices |
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