CN108628099A - Red pixel photosensitive composition, colour filter and its application - Google Patents
Red pixel photosensitive composition, colour filter and its application Download PDFInfo
- Publication number
- CN108628099A CN108628099A CN201810201456.2A CN201810201456A CN108628099A CN 108628099 A CN108628099 A CN 108628099A CN 201810201456 A CN201810201456 A CN 201810201456A CN 108628099 A CN108628099 A CN 108628099A
- Authority
- CN
- China
- Prior art keywords
- mentioned
- red pixel
- photosensitive composition
- chemical formula
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- 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
-
- 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
- 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
- G03F7/027—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
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Nonlinear Science (AREA)
- Structural Engineering (AREA)
- Architecture (AREA)
- Mathematical Physics (AREA)
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials For Photolithography (AREA)
- Optical Filters (AREA)
Abstract
The present invention provides red pixel photosensitive composition, the colour filter formed using red pixel photosensitive composition and its application, above-mentioned red pixel photosensitive composition includes alkali soluble resins, photopolymerizable compound, Photoepolymerizationinitiater initiater, colorant and solvent, above-mentioned Photoepolymerizationinitiater initiater includes the oxime ester fluorenes system Photoepolymerizationinitiater initiater of specific structure, and above-mentioned colorant includes bromination diketopyrrolo-pyrrole compound.The adaptation and hardness of the red pixel photosensitive composition of the present invention are excellent and can inhibit the speckle that develops.
Description
Technical field
The present invention relates to red pixel photosensitive composition, colour filter and image display devices, in more detail
For, be related to adaptation and hardness it is excellent and inhibit development speckle occur red pixel photosensitive composition,
The colour filter formed using the red pixel photosensitive composition and the image for having above-mentioned colour filter show dress
It sets.
Background technology
Colour filter is widely used in photographing element, liquid crystal display device (LCD) etc., and application range is expanding.Colour filter
Device is generally as follows manufacture：On the substrate for being formed with black matrix pattern, equably coating, which contains, is equivalent to red, green and blue
Each color pigment photosensitive composition, then heat drying, it is exposed and developed to be formed by film,
It is further heating and curing as needed, aforesaid operations is repeated to each color, form assorted pixel.
A kind of red pixel coloring phototonus resin group is disclosed in KR published patent the 10-2012-0112188th
Close object, colorant of the benzimidazolone pigment for using brightness and contrast high as red pixel.
However, in order to provide the colour filter of the high-quality with high colorrendering quality, it is desirable that excellent for adaptation and hardness
The exploitation of red pixel photosensitive composition that is different and inhibiting development speckle generation.
Invention content
Project to be solved
Red pixel that is excellent it is an object of the present invention to provide adaptation and hardness and inhibiting development speckle to occur
Use photosensitive composition.
Another object of the present invention is to provide formed using above-mentioned red pixel photosensitive composition
Colour filter.
Of the invention and another purpose is, provides the image display device for having above-mentioned colour filter.
The method to solve the problem
On the one hand, the present invention provides a kind of red pixel photosensitive composition, it includes alkali soluble resins,
Photopolymerizable compound, Photoepolymerizationinitiater initiater, colorant and solvent, above-mentioned Photoepolymerizationinitiater initiater include 1 table of following chemical formula
The compound shown, above-mentioned colorant include the compound represented by following chemical formula 2.
[chemical formula 1]
[chemical formula 2]
In above-mentioned formula,
R1~R3It is each independently hydrogen, halogen, C1-C20Alkyl, aryl, C1-C20Alkoxy, aralkyl, C1-C20
Hydroxy alkyl, C2-C40Hydroxy alkoxy alkyl or C3-C20Naphthenic base；
R4~R10It is each independently hydrogen, C1-C20Alkyl, aryl, C1-C20Alkoxy, aralkyl, C1-C20Hydroxyl
Base alkyl, C2-C40Hydroxy alkoxy alkyl, C3-C20Naphthenic base, amino, nitro, cyano or hydroxyl；
P is 0 or 1.
On the other hand, the present invention provides the colour filter formed using above-mentioned red pixel photosensitive composition
Device.
Another aspect, the present invention provide the image display device characterized by having above-mentioned colour filter.
Invention effect
The red pixel photosensitive composition of the present invention is poly- by the oxime ester fluorenes system light comprising specific structure
Initiator is closed as Photoepolymerizationinitiater initiater, and includes bromination diketopyrrolo-pyrrole compound as colorant, thus adaptation
It is excellent with hardness and the speckle that develops can be inhibited.
Specific implementation mode
Hereinafter, the present invention is described in more detail.
One embodiment of the present invention is related to a kind of red pixel photosensitive composition, and it includes alkali solubilities
Resin (A), photopolymerizable compound (B), Photoepolymerizationinitiater initiater (C), colorant (D) and solvent (E), above-mentioned Photoepolymerizationinitiater initiater
Include the oxime ester fluorenes system Photoepolymerizationinitiater initiater of specific structure, above-mentioned colorant includes bromination diketopyrrolo-pyrrole compound.
Alkali soluble resins (A)
In one embodiment of the present invention, above-mentioned alkali soluble resins (A) is as long as used in developing procedure
The soluble ingredient of alkaline developer imparting, which can be dissolved in alkaline developer, to be used without limitation.It is aobvious in order to be dissolved in alkali
Shadow liquid, it is general mode to import carboxyl into resin and assign acid value.Above-mentioned alkali soluble resins (A) can be by that will have carboxylic
The ethylene unsaturated monomer (a1) of base is copolymerized with the other monomers (a3) that can be copolymerized with above-mentioned monomer and is manufactured, or
It is manufactured by making acid anhydrides be reacted with the resin copolymer (a2) with hydroxyl to assign acid value.
The acid value of above-mentioned alkali soluble resins (A) is preferably 30~200mgKOH/g.The acid value of alkali soluble resins (A) is less than
In the case of 30mgKOH/g, red pixel is difficult to ensure sufficient developing powder with photosensitive composition, more than
In the case of 200mgKOH/g, decline with the adaptation of substrate, be easy to happen the short circuit of pattern, and under the compatibility of colorant
It drops and the colorant precipitation in red pixel photosensitive composition or red pixel coloring phototonus resin
The storage stability of composition reduces and viscosity is easy to increase.
As the concrete example of the above-mentioned ethylene unsaturated monomer (a1) 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；And the acid anhydrides of above-mentioned 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.
As making acid anhydrides be reacted with the above-mentioned resin copolymer (a2) with hydroxyl the method to assign acid value, having makes
Acid anhydrides is further reacted to assign the mode of acid value with dihydroxypropyl lipin polymer, and but it is not limited to this.
As above-mentioned dihydroxypropyl esters, (methyl) acrylic acid 2- hydroxy methacrylates, (methyl) can be typically enumerated
(the first such as acrylic acid 2- hydroxy propyl esters, (methyl) acrylic acid 4- hydroxybutyls, (methyl) acrylic acid 2- hydroxyl -3- phenoxy-propyls
Base) hydroxyalkyl acrylates etc..
It, can be with other lists of the copolymerization of the ethylene unsaturated monomer with carboxyl when manufacturing above-mentioned alkali soluble resins (A)
Body (a3) is although be illustrated in the following, but being not necessarily limited to this：
Styrene, vinyltoluene, α-methylstyrene, p-chlorostyrene, o-methoxystyrene, meta-methoxy benzene second
Alkene, to methoxy styrene, adjacent vinyl benzyl methyl ether, vinyl benzyl methyl ether, to vinyl benzyl methyl ether, neighbour
Vinylbenzyl glycidyl ether, vinylbenzyl glycidyl ether, to the aromatic series second such as vinylbenzyl glycidyl ether
Alkenyl compound；
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 cyclohexyls, (methyl)
Acrylic acid tricyclic [5.2.1.02,6] decane -8- base esters, bis- cyclopentyloxy ethyl esters of (methyl) acrylic acid 2-, (methyl) acrylic acid is different
Alicyclic (methyl) esters of acrylic acid such as norbornene ester；
(methyl) the benzyl acrylate classes such as (methyl) phenyl acrylate, (methyl) benzyl acrylate；
3- (methacryloxymethyl) oxetanes, 3- (methacryloxymethyl) -3- Ethyloxetanes,
3- (methacryloxymethyl) -2- trifluoromethyls oxetanes, 3- (methacryloxymethyl) -2- phenyl oxa- ring fourths
Alkane, 2- (methacryloxymethyl) oxetanes, 2- (methacryloxymethyl) -4- trifluoromethyl oxetanes etc.
Unsaturated oxetane compound etc..
The above-mentioned monomer illustrated as the other monomers that can be copolymerized (a3) can be respectively individually or by two or more combinations
It uses.
Relative to the 100 weight % of all solids ingredient in red pixel photosensitive composition, above-mentioned alkali
The content of soluble resin (A) can be 10~80 weight %, preferably can be 10~70 weight %.In above-mentioned alkali soluble resins
(A) content be above range in the case of, for developer solution dissolubility fully and can be easy to form pattern.
Photopolymerizable compound (B)
In one embodiment of the present invention, above-mentioned photopolymerizable compound (B) is by following Photoepolymerizationinitiater initiaters (C)
The compound that acts on and can polymerize can use monofunctional monomer, two functional monomers or other polyfunctional monomers, preferably may be used
To use the polyfunctional monomer of two functions or more.
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 or 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
(acrylyl oxy-ethyl) ether or 3- methyl pentanediols two (methyl) acrylate etc., but it is not limited to this.
As the concrete example of other above-mentioned polyfunctional monomers, can enumerate trimethylolpropane tris (methyl) acrylate,
Ethoxylated trimethylolpropane three (methyl) acrylate, propoxylation trimethylolpropane tris (methyl) acrylate, season
Penta tetrol three (methyl) acrylate, pentaerythrite four (methyl) acrylate, dipentaerythritol five (methyl) acrylate, second
Oxygroup dipentaerythritol six (methyl) acrylate, (methyl) acrylate of propoxylated dipentaerythritol six or two seasons penta 4
Alcohol six (methyl) acrylate etc., but it is not limited to this.
Relative to the 100 weight % of all solids ingredient in red pixel photosensitive composition, above-mentioned light
The content of polymerizable compound (B) can be 1~45 weight %, preferably can be 3~45 weight %.In above-mentioned optical polymerism
In the case of the content of object (B) is closed as above range, the intensity of pixel portion or flatness can be made to become good.
Photoepolymerizationinitiater initiater (C)
In one embodiment of the present invention, above-mentioned Photoepolymerizationinitiater initiater (C) is as causing above-mentioned optical polymerism chemical combination
The compound of the polymerization of object (B), including oxime ester fluorenes system Photoepolymerizationinitiater initiater.In particular, by comprising represented by following chemical formula 1
Photoepolymerizationinitiater initiater as above-mentioned oxime ester fluorenes system Photoepolymerizationinitiater initiater, to above-mentioned red pixel coloring phototonus resin group
It closes object high-sensitivity and the time for exposure is made to shorten, thus, it is possible to show high-resolution while improving pattern.
[chemical formula 1]
In above-mentioned formula,
R1~R3It is each independently hydrogen, halogen, C1-C20Alkyl, aryl, C1-C20Alkoxy, aralkyl, C1-C20
Hydroxy alkyl, C2-C40Hydroxy alkoxy alkyl or C3-C20Naphthenic base；
R4~R10It is each independently hydrogen, C1-C20Alkyl, aryl, C1-C20Alkoxy, aralkyl, C1-C20Hydroxyl
Base alkyl, C2-C40Hydroxy alkoxy alkyl, C3-C20Naphthenic base, amino, nitro, cyano or hydroxyl；
P is 0 or 1.
C as used in this specification1-C20Alkyl refer to by 1~20 straight chain type or branch constituted of carbon atom number
1 valency alkyl of type, for example, including methyl, ethyl, n-propyl, isopropyl, normal-butyl, isobutyl group, tertiary butyl, n-pentyl, n-hexyl,
N-heptyl, n-octyl, n-nonyl, positive decyl, n-undecane base etc., but it is not limited to this.
Aryl as used in this specification includes whole aromatic group and heteroaromatic group and their quilt
The derivative of partial reduction.Above-mentioned aromatic group is 5 yuan~15 yuan of monocycle or thick cyclic group, heteroaromatic group refer to
Include the aromatic group of more than one oxygen, sulphur or nitrogen.As the example of representative aryl, there are phenyl, naphthalene, pyridyl group
(pyridinyl), furyl (furanyl), thienyl (thiophenyl), indyl (indolyl), quinolyl
(quinolinyl), imidazolinyl (imidazolinyl),Oxazolyl (oxazolyl), thiazolyl (thiazolyl), tetrahydrochysene
Naphthalene etc., but it is not limited to this.
C as used in this specification1-C20Alkoxy refer to by 1~20 straight chain type constituted of carbon atom number or branch
Chain alkoxy, including methoxyl group, ethyoxyl, positive propoxy etc., but it is not limited to this.
Aralkyl (aralkyl group) as used in this specification refers to that substitution has aryl (fragrance on the carbon of alkyl
Race's alkyl) compound group, such as including benzyl, phenethyl etc., but it is not limited to this.
C as used in this specification1-C20Hydroxy alkyl refer to the straight of the carbon atom number 1~20 being optionally substituted by a hydroxyl group
Chain or branched chain type alkyl, such as including hydroxymethyl, hydroxyethyl, hydroxypropyl etc., but it is not limited to this.
C as used in this specification2-C40Hydroxy alkoxy alkyl refer to carbon atom number 1~20 alkyl carbon
It is upper replace have the compound group of alkoxy, the alkoxy be replace have hydroxyl by 1~20 straight chain constituted of carbon atom number
The alkoxy of type or branched chain type, such as including hydroxymethoxy methyl, hydroxyethoxymethyl, hydroxymethoxy ethyl etc., but
It is not limited to this.
C as used in this specification3-C20Naphthenic base refer to by 3~20 monocycles constituted of carbon atom number or condensed ring
Shape alkyl, such as including cyclopropyl, cyclobutyl, cyclopenta, cyclohexyl etc., but it is not limited to this.
In one embodiment of the present invention, R1~R3It is each independently hydrogen, C1-C6Alkyl or phenyl, R4~R10Respectively
It independently is hydrogen or nitro, p can be 0.
In one embodiment of the present invention, R1~R3It is each independently hydrogen or C1-C6Alkyl, R4~R10For hydrogen, p can
Think 1.
For example, the Photoepolymerizationinitiater initiater represented by the above-mentioned chemical formula 1 for being 0 as p, can enumerate following compounds.
In addition.For example, the Photoepolymerizationinitiater initiater represented by the above-mentioned chemical formula 1 for being 1 as p, can enumerate following chemical combination
Object.
In one embodiment of the present invention, above-mentioned Photoepolymerizationinitiater initiater (C) is in addition to the photopolymerization represented by above-mentioned chemical formula 1
It can be further included other than initiator selected from by acetophenone based compound, benzophenone based compound, triazine based compound, connection
One or more of the group of imidazole compound, oxime compound and thioxanthones based compound composition compound.
Relative to the whole 100 weight % of solid constituent in red pixel photosensitive composition, above-mentioned light
The content of polymerization initiator (C) can be 0.1~30 weight %, be specifically as follows 0.1~10 weight %.Draw in above-mentioned photopolymerization
In the case of sending out the content of agent within the above range, the generation pattern in developing procedure can be prevented due to sensitivity declines
The phenomenon of short circuit, and can prevent due to excessive reaction cross-linking reaction from excessively generating what the physical property of gauffer and film declined
Phenomenon.
Colorant (D)
In one embodiment of the present invention, above-mentioned colorant (D) includes the bromination diketone pyrroles represented by following chemical formula 2
And azole compounds are as pigment.
[chemical formula 2]
Above-mentioned colorant (D) can further include compound and the work of C.I. paratoneres 177 represented by following chemical formula 3
For pigment.
[chemical formula 3]
The compound represented by compound and above-mentioned chemical formula 3 represented by above-mentioned chemical formula 2 can be synthesized directly and be made
With, or buy commercially available form and use.As the commercial articles of the compound represented by above-mentioned chemical formula 2, there is BASF
Company3620 CF of Red S have C.I. as the commercial articles of the compound represented by above-mentioned chemical formula 3
Paratonere 254.
Compound represented by above-mentioned chemical formula 2 can be with 1 with the compound represented by above-mentioned chemical formula 3:9~9:1
Weight ratio includes.
Relative to the whole 100 weight % of colorant, the content of the compound represented by above-mentioned chemical formula 2 can be 5~60
Weight %, relative to the whole 100 weight % of colorant, the content of the compound represented by above-mentioned chemical formula 3 can be 5~60 weights
% is measured, relative to the whole 100 weight % of colorant, the content of above-mentioned C.I. paratoneres 177 can be 5~70 weight %.
Compound represented by compound, chemical formula 3 and C.I. paratoneres 177 represented by above-mentioned chemical formula 2 contain
In the case that amount is respectively lower than above range, tinting strength, tinting power may decline, and in the case larger than the above-mentioned range, pattern forms possibility
The reason of becoming difficult and declining as closing force.
If compound represented by compound, chemical formula 3 and C.I. paratoneres 177 represented by above-mentioned chemical formula 2
Content meets above-mentioned content range respectively, then can prevent closing force from declining, and can increase reliability.
Above-mentioned colorant is in addition to the compound represented by above-mentioned chemical formula 2, the compound represented by chemical formula 3 and C.I. face
Expect that other than red 177 other pigment can be further included.
Above-mentioned pigment can use the organic pigment or inorganic pigment used generally in the art.In addition, above-mentioned pigment root
It can also implement processing below according to needs：Rosin processing；Utilize the pigment derivative for being imported with acidic-group or basic group
Deng surface treatment；It is handled using the grafting for surface of pigments of high-molecular compound etc.；Utilize sulfuric acid particles method etc.
Micronized processing；Utilize the carrying out washing treatment for removing deimpurity organic solvent or water etc.；Or using ion-exchange etc. from
Removal processing of sub- property impurity etc..
Above-mentioned organic pigment can specifically enumerate water-soluble azo pigment, insoluble azo colour, phthalocyanine color, quinacridine
Ketone pigment, isoindolenone pigments, isoindoline pigment, pigment, pyrene ketone pigment, twoPiperazine pigment, anthraquinone pigment, two anthracenes
Quinonyl pigment, anthracene pyrimidine pigment, anthanthrone (anthanthrone) pigment, indanthrone (indanthrone) pigment, flavane scholar
Ketone pigment, pyranthrone (pyranthrone) pigment, diketopyrrolo-pyrrole pigment etc..
As above-mentioned inorganic pigment, the metallic compounds such as metal oxide or metallic complex salt can be enumerated, specifically, can
With oxide or the metal composite oxide etc. for enumerating the metals such as iron, cobalt, aluminium, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony.
In particular, as above-mentioned organic pigment and inorganic pigment, specifically, colour index (association of dyeing man can be enumerated
Will (The society of Dyers and Colourists) is published) in be classified as the compound of pigment, more specifically,
The pigment that following colour index (C.I.) number can be enumerated, but is not necessarily limited to this, they can be respectively individually or by two
Kind combination of the above uses.
C.I. Pigment Red 9,97,105,122,123,144,149,166,168,176,180,192,208,215,216,
224,242,255 and 264
Above-mentioned pigment can be used together yellow uitramarine with above-mentioned red pigment, specifically, can be referred to using following color
The yellow uitramarine of number (C.I.) number.
C.I. pigment yellow 13,20,24,31,53,83,86,93,94,109,110,117,125,137,138,139,147,
148,150,153,154,166,173,180 and 185
C.I. pigment orange 13,31,36,38,40,42,43,51,55,59,61,64,65 and 71
Above-mentioned pigment can be respectively used singly or in combination of two or more.
It is preferable to use the dispersible pigment dispersions that its uniform particle sizes disperses for above-mentioned pigment.As the uniform particle sizes point for making pigment
The example of scattered method can enumerate the method etc. for carrying out decentralized processing by adding pigment dispersing agent, can according to this method
To obtain the dispersible pigment dispersion of pigment evenly dispersed state in the solution.
As the concrete example of above-mentioned pigment dispersing agent, can enumerate cationic system, anionic system, nonionic system, both sexes from
Surfactants such as subsystem, Polyester, polyamine system etc., they can respectively individually or be used in combination of two or more.
Above-mentioned pigment dispersing agent is can unlimitedly to use ability in order to which the solution of pigment is solidifying and maintains stability and adds
The pigment dispersing agent generally used in domain.
Preferably comprise includes butyl methacrylate (BMA) or methacrylic N, N-dimethylamino ethyl ester (DMAEMA)
Acrylic ester dispersant (hereinafter referred to as dispersant containing acrylic) be preferred.At this point, above-mentioned dispersant containing acrylic preferably makes
With by the substance that active control method manufactures disclosed in KR published patent 2004-0014311, as passing through above-mentioned work
Property control method manufacture acrylic ester dispersant commercially available product, DISPER BYK-2000, DISPER BYK- can be enumerated
2001, DISPER BYK-2070, DISPER BYK-2150 etc..
Foregoing illustrative dispersant containing acrylic can respectively individually or be used in combination of two or more.
Above-mentioned pigment dispersing agent can also use the pigment of other resin types other than above-mentioned dispersant containing acrylic to disperse
Agent.As the pigment dispersing agent of other above-mentioned resin types, the pigment dispersing agent of well known resin type, especially poly- ammonia can be enumerated
Ester, using polyacrylate as the polycarboxylate of representative, (part) amine salt, the polycarboxylic acids of unsaturated polyamide, polycarboxylic acids, polycarboxylic acids
Ammonium salt, the alkylamine salt of polycarboxylic acids, polysiloxanes, long-chain polyaminoamide phosphate, hydroxyl polycarboxylic acids ester and they
Modification product or with freely (free) carboxyl polyester and poly- (low-grade alkylidene imines) the amide for reacting and being formed
Or oily dispersant as their salt；(methyl) acrylic-styrene copolymer, (methyl) acrylic acid-(methyl) propylene
Water-soluble resin or water-soluble as acid ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol or polyvinylpyrrolidone
Property polymer compound；Polyester；Modified polyacrylate；The addition product of ethylene oxide/propylene oxide；With phosphate etc..
As the commercially available product of above-mentioned resin type dispersant, for cationic system pitch dispersant, for example, BYK (Bi Ke)
The 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；The trade name of Lubrizol (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..The pigment dispersing agent of other resin types other than above-mentioned dispersant containing acrylic can be with
Respectively individually or be used in combination of two or more, can also be used in combination with dispersant containing acrylic.
Relative to 100 parts by weight of used pigment, the usage amount of above-mentioned pigment dispersing agent can be 5~60 parts by weight,
More preferably can be 15~50 parts by weight ranges.If the content of pigment dispersing agent in terms of said reference more than 60 parts by weight,
Viscosity may increase, and less than 5 parts by weight, the micronized of pigment is difficult, or may lead to gelation etc. after disperseing
Problem.
In one embodiment of the present invention, above-mentioned colorant (D) can further include more than one dyestuff.
As long as above-mentioned dyestuff there is dissolubility unlimitedly to use organic solvent.It is preferable to use both have pair
The reliabilities such as dissolubility and solvent resistance for alkaline developer, ageing stability are may insure again in the dissolubility of organic solvent
Dyestuff.
As above-mentioned dyestuff, the acid dyes selected from the acidic-group with sulfonic acid or carboxylic acid etc., acidity can be used to contaminate
Substance in material and the salt of nitrogenous compound, the sulfonamide body of acid dyes etc. and their derivative in addition to this can also
Select the acid dyes and their derivative of azo system, xanthene system, phthalocyanine system.
Preferably, above-mentioned dyestuff can enumerate colour index (association of dyeing man will (The society of Dyers and
Colourists) publish) in be classified as dyestuff compound or the well known dyestuff described in dyeing handbook (Se Ran societies).
Relative to the solid constituent whole 100 weight % in red pixel photosensitive composition, above-mentioned
The content of toner (D) can be 1~60 weight %, preferably can be 5~50 weight %.It is in the content of above-mentioned colorant (D)
In the case of above range, though formed it is abundant if the colour saturation of film pixel, when development the deciduous of non-pixel portion will not drop
It is low, therefore it is not likely to produce residue, thus preferably.
In the present invention, so-called solid constituent refers to the residual components other than solvent.
Solvent (E)
In one embodiment of the present invention, above-mentioned solvent (E) is as long as making red pixel coloring phototonus resin combination
Other compositions included in object are effective when dissolving, then can use common coloring phototonus resin group without particular limitation
Close the solvent used in object, particularly preferably ethers, acetate esters, aromatic hydrocarbon, ketone, alcohols or esters etc..
As above-mentioned ethers, for example, ethylene glycol single methyl ether, ethylene glycol monomethyl ether, ethylene glycol monopropyl ether
With the ethylene glycol monoalkyl ethers class such as ethylene glycol monobutyl ether；Diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol
The diethylene glycol dialkyl ethers class such as dipropyl ether and diethylene glycol dibutyl ether；Propylene glycol monomethyl ether etc..
As above-mentioned acetate esters, for example, methylcellosolve acetate, ethyl cellosolve acetate, acetic acid second
Ester, butyl acetate, pentyl acetate, methyl lactate, ethyl lactate, butyl lactate, 3- methoxybutyls acetic acid esters, 3- methyl -3-
Methoxyl group -1- butylacetic acids ester, methoxypentyl acetic acid esters, ethylene glycol acetate, ethylene acetate, 3- methoxy propyls
Sour methyl esters, 3- methoxyl group -1- butylacetic acids ester, ethylene glycol monobutyl ether acetic acid esters, diethylene glycol monoethyl ether acetic acid esters, dipropyl
Glycol methylether acetate, 1,3 butylene glycol diacetate esters, diethylene glycol monobutyl ether acetic acid esters, ethylene glycol single methyl ether acetic acid
Ester, ethylene glycol monomethyl ether acetate, diethylene glycol monoacetate, diethylene glycol diacetate esters, diethylene glycol monobutyl ether second
Acid esters, Propylene glycol monoacetate, propylene-glycol diacetate, propylene glycol monomethyl ether, propylene glycol monoethyl acetic acid esters,
Ethylene carbonate and propylene carbonate etc..
As above-mentioned aromatic hydrocarbon, for example, benzene,toluene,xylene and mesitylene etc..
As above-mentioned ketone, for example, methyl ethyl ketone, acetone, methyl amyl ketone, methyl iso-butyl ketone (MIBK) and ring
Hexanone etc..
As above-mentioned alcohols, for example, ethyl alcohol, propyl alcohol, butanol, hexanol, cyclohexanol, ethylene glycol, glycerine and 4- hydroxyls
Base -4-methyl-2 pentanone etc..
As above-mentioned esters, for example, 3- ethoxyl ethyl propionates, 3- methoxy methyl propionates and gamma-butyrolacton
Deng.
Above-mentioned solvent can respectively individually or be use mixing two or more.
From the aspect of coating and drying property, above-mentioned solvent is 100 DEG C~200 DEG C organic molten it is preferable to use boiling point
Agent, for example, aklylene glycol alkylether acetates class, alkylene glycol monoalkyl ethers class, ketone, esters, more preferably
Propylene glycol monomethyl ether, propylene glycol monoethyl acetic acid esters, propylene glycol monomethyl ether, cyclohexanone, lactic acid can be enumerated
Ethyl ester, butyl lactate, 3- ethoxyl ethyl propionates and 3- methoxy methyl propionates etc..
Relative to the red pixel whole 100 weight % of photosensitive composition, the content of above-mentioned solvent (E) can
Think 60~90 weight %.If the content of above-mentioned solvent is within the above range, roll coater, spin coater, slit are being utilized
When the apparatus for coating such as formula spin coater, slit type coater (otherwise referred to as die coating machine) and flush coater are coated, coating can
To become good.
Additive (F)
Other macromolecule chemical combination can be used together with photosensitive composition as needed for the red pixel of the present invention
The additives such as object, curing agent, surfactant, closely sealed accelerating agent, antioxidant, ultra-violet absorber, anticoagulant.
As the concrete example of other above-mentioned high-molecular compounds, it is solid that epoxy resin, maleimide resin etc. can be enumerated
The heat such as the property changed resin, polyvinyl alcohol, polyacrylic acid, polyalkylene glycol monoalkyl ether, poly- fluoroalkyl, polyester, polyurethane
Plastic resin etc..
Above-mentioned curing agent is used to realize deeply-curing and improve mechanical strength, as the concrete example of curing agent,
Epoxide, polyfunctional isocyanate compound, melamine compound, oxetane compound etc. can be enumerated.
As the concrete example of the epoxide in above-mentioned curing agent, bisphenol A type epoxy resin, A Hydrogenated Bisphenol A can be enumerated
A types 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 this 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..
As the concrete example of the oxetane compound in above-mentioned curing agent, carbonic ester dioxygen heterocycle fourth can be enumerated
Alkane, dimethylbenzene dioxygen azetidine, adipate ester dioxygen azetidine, terephthalate dioxygen azetidine, hexamethylene two
Carboxylic acid dioxygen azetidine etc..
Foregoing illustrative curing agent can be independent or be use mixing two or more.
Above-mentioned curing agent can also be used in combination with curing compound is helped, described to help curing compound that make together with curing agent
The epoxy group of epoxide, the oxetanes scaffolds open polymerization of oxetane compound.It is above-mentioned to help curing compound
Such as have polybasic carboxylic acid class, polybasic carboxylic acid anhydride, acid agent etc..Above-mentioned polybasic carboxylic acid anhydride can utilize commercially available epoxy resin solid
Agent.As the concrete example of above-mentioned epoxy curing agent, can enumerate ADEKA HARDENER EH-700 (trade name,
ADEKA industry (strain) manufacture), RIKACID HH (trade name, new Japan Chemical (strain) manufacture), MH-700 (trade name, new Japan
Physics and chemistry (strain) manufactures) etc..
Above-mentioned surfactant can use to more improve the envelope formative of photosensitive polymer combination, preferably
Fluorine system surfactant or silicone based surfactants etc. can be used.
Above-mentioned silicone based surfactants for example as commercially available product have DOW CORNING Dong Li organosilicons company DC3PA,
DC7PA, SH11PA, SH21PA, SH8400 etc., TSF-4440, TSF-4300 of organosilicon company of GE Toshiba, TSF-4445,
TSF-4446, TSF-4460, TSF-4452 etc..Above-mentioned fluorine system surfactant for example has big Japanese ink chemistry as commercially available product
MEGAFAC F-470 of industrial group, F-471, F-475, F-482, F-489 etc..Foregoing illustrative surfactant can be each
From 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, 3- isocyanate group propyl
Triethoxysilane etc..Foregoing illustrative closely sealed accelerating agent can respectively individually or be used in combination of two or more.Relative to red
The whole 100 weight % of solid constituent in color pixel photosensitive composition, the content of above-mentioned closely sealed accelerating agent are logical
It often can be 0.01~10 weight %, preferably can be 0.05~2 weight %.
As the concrete example of above-mentioned antioxidant, 2,2'- thiobis (4- methyl-6-tert-butylphenols), 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 bases phenyl)-can be enumerated
5- chlorobenzotriazoles, alkoxy benzophenone etc..
As the concrete example of above-mentioned anticoagulant, Sodium Polyacrylate etc. can be enumerated.
The red pixel photosensitive composition of one embodiment of the present invention can for example pass through such as lower section
Method manufactures.
First, the pigment in above-mentioned colorant (D) is mixed with solvent (E), the flat of pigment is dispersed to using ball mill etc.
Equal grain size is 0.2 μm or less degree.At this point, as needed, can make pigment dispersing agent, alkali soluble resins (A) a part or
Whole or dyestuff mix with solvent (E) and dissolve or disperse together.In the dispersion liquid of above-mentioned mixing, to reach scheduled dense
The mode of degree further adds remaining alkali soluble resins (A), Photoepolymerizationinitiater initiater (C), photopolymerizable compound (B) and addition
Agent (F) and solvent as needed (E), so as to manufacture the photosensitive composition of the present invention.
One embodiment of the present invention relates to the use of above-mentioned red pixel photosensitive composition and is formed
Colour filter.The colour filter of one embodiment of the present invention is characterized in that, above-mentioned red pixel is coated on substrate and is used
Be exposed in a predetermined pattern after color sensation photosensitive resin composition and develop and the dyed layer that is formed.
Hereinafter, being carried out for the pattern forming method of the red pixel photosensitive composition using the present invention
It is described in detail.
This skill can be used using the method that the red pixel photosensitive composition of the present invention forms pattern
Well known method in art field, generally includes application step, step of exposure and removal step.By by the present invention red pixel
It is coated on base material with photosensitive composition, carries out photocuring and development and form pattern, so as to be used as
Color pixel (rendered image).
Above-mentioned application step is, by the red pixel of the present invention with photosensitive composition be coated on base material (though
So there is no limit, but usually glass or silicon chip) or the photosensitive polymer combination layer that is previously formed on and carry out predrying, from
And the volatile ingredients such as solvent are removed come the step of obtaining smooth film.At this point, the thickness of film is preferably 1~3 μm.
Above-mentioned step of exposure is, in order to obtain target pattern from above-mentioned film, is irradiated to specific region by mask ultraviolet
Line and the step of make its solidification.At this point, in order to equably irradiate parallel rays to entire exposure portion, and keep mask accurate with substrate
Ground aligns, it is preferable to use the devices such as mask registration exposure machine (Mask Aligner) or step-by-step exposure machine (Stepper).
Above-mentioned removal step is that complete cured film by making irradiation ultraviolet light contacts with aqueous alkali, makes non-exposure
Light region soluble simultaneously develops, the step of to obtain target pattern.After development, as needed, can 140~200 DEG C, especially
It is dry after 10~60 minutes degree of implementation at about 150 DEG C.
The developer solution used in above-mentioned development can unlimitedly use substance well known in the art, usually can be with
Use the aqueous solution for including alkali compounds and surfactant.
Above-mentioned alkali compounds can be inorganic or organic basic compound.As the specific of above-mentioned inorganic alkaline compound
Example, can enumerate sodium hydroxide, potassium hydroxide, disodium hydrogen phosphate, sodium dihydrogen phosphate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate, phosphoric acid
Potassium dihydrogen, sodium metasilicate, potassium silicate, sodium carbonate, potassium carbonate, sodium bicarbonate, saleratus, Boratex, potassium borate, ammonia etc..In addition,
As the concrete example of above-mentioned organic basic compound, tetramethylammonium hydroxide, 2- hydroxyethyl trimethyl hydroxides can be enumerated
Ammonium, monomethylamine, dimethylamine, trimethylamine, mono aminoethane, diethylamine, triethylamine, single isopropylamine, diisopropylamine, ethanol amine etc..These
Inorganic and organic basic compound can respectively be used alone or in combination of two or more.In developer solution, above-mentioned alkali compounds
Content can be 0.01~10 weight %, preferably 0.03~5 weight %.
Above-mentioned surfactant can be used selected from by nonionic surfactants, anionic surfactant and sun
One kind in the group of ionization series surfactant composition or their mixture.Tool as above-mentioned nonionic surfactants
Body example can enumerate polyoxyethylene alkyl ether, polyoxyethylene aryl ether, polyoxyethylene alkylaryl ether, polyoxyethylene in addition
Derivative, ethylene oxide/propylene oxide block copolymer, sorbitan fatty ester, polyoxyethylene sorbitan
It is aliphatic ester, polyoxyethylene sorbitol aliphatic ester, fatty glyceride, polyoxyethylene fatty acid ester, polyxyethylated
Amine etc..As the concrete example of above-mentioned anionic surfactant, laruyl alcohol sodium sulfovinate or oleyl sulfate sodium can be enumerated
Alkylsurfuric acids salt, the neopelexes such as equal higher alcohol sulfates salt, NaLS or Texapon Special
Or alkylaryl sulfonates class such as dodecyl sodium naphthalene sulfonate etc..It, can as the concrete example of above-mentioned cationic system surfactant
To enumerate the amine salt such as stearyl amine hydrochloride or lauryl trimethyl ammonium chloride or quaternary ammonium salt etc..Above-mentioned surfactant can be independent
Or it is used in combination.In developer solution, content typically 0.01~10 weight % of above-mentioned surfactant, preferably
It can be 0.05~8 weight %, more preferably can be 0.1~5 weight %.
One embodiment of the present invention is related to the image display device for having above-mentioned colour filter.
The colour filter of the present invention can be applied not only to common liquid crystal display device (LCD), and can be applied to electricity
Photoluminescence display device (EL), plasm display device (PDP), field-emission display device (FED), organic illuminating element
(OLED) the various image display devices such as.
The image display device of the present invention is other than having above-mentioned colour filter, including structure known in the art
At.
The image display device of one embodiment of the present invention can be further equipped with other than above-mentioned colour filter and include
Red pattern layer containing red quantum dot particle, the green pattern layer containing green quantum dot particles and contain blue quantum
The colour filter of the blue color patterns layer of point particle.Under such circumstances, do not have applied to the light that sends out of the light source of image display device
It is particularly limited to, but from the aspect of superior colorrendering quality, can preferably use the light source for sending out blue light.
The image display device of one embodiment of the present invention can also be further equipped with only other than above-mentioned colour filter
Include the colour filter of the pattern layer of two kinds of colors in red pattern layer, green pattern layer and blue color patterns layer.Such situation
Under, above-mentioned colour filter is further equipped with the transparent pattern layer without quantum dot particles.Only have the feelings of the pattern layer of two kinds of colors
Under condition, the light source for the light for sending out the wavelength that remaining color for not including is presented can be used.For example, only including red pattern layer
In the case of green pattern layer, the light source for sending out blue light can be used.Under such circumstances, red quantum dot particle is sent out
Red light, green quantum dot particles send out green light, and transparent pattern layer is directed through blue light and blue is presented.
Hereinafter, by embodiment, comparative example and experimental example, it is more particularly described the present invention.These embodiments, comparative example and reality
It tests example and is merely to illustrate the present invention, it will be apparent to one skilled in the art that the scope of the present invention is not limited by this.
Synthesis example 1:The synthesis of Photoepolymerizationinitiater initiater (C-1)
Reaction 1.
So that 2- nitrofluorenes 5.0g is dissolved in anhydrous nitrobenzene 100ml, anhydrous Aluminum chloride 6.31g is added, then by reactant
45 DEG C are warming up to, was slowly added to that chloroacetic chloride 2.79g is made to be dissolved in solution made of anhydrous nitrobenzene 30ml through 30 minutes, will react
Object is warming up to 65 DEG C and stirs 1 hour.Then, reactant is cooled to room temperature, distilled water 70ml is added and stirs 30 minutes left sides
Behind the right side, product is filtered.So that the solid product of gained is scattered in the ether of 50ml, is filtered after being stirred at room temperature 30 minutes
And it is dry, to obtain lurid reactant 1 (1- (9,9-H-7- nitrofluorene -2- bases)-ethyl ketone) 5.08g.
Reaction 2.
So that reactant 1 (1- (9,9-H-7- nitrofluorene -2- bases)-ethyl ketone) 1.5g is scattered in ethyl alcohol 30ml, hydrochloric acid hydroxyl is added
Then reaction solution is slowly heated up and carries out 2 hours return stirrings by amine 0.49g and sodium acetate 0.58g.Reactant is cooled to
Room temperature stirs 30 minutes or so after distilled water 20ml is added, and the solid product of gained is filtered, after being washed with distilled water repeatedly
It is dry, to obtain grayish reactant 2 (1- (9,9-H-7- nitrofluorene -2- bases)-acetophenone oxime) 1.38g.
Reaction 3.
So that reactant 2 (1- (9,9-H-7- nitrofluorene -2- bases)-acetophenone oxime) 1.20g is scattered in ethyl acetate 50ml, is added
Then reaction solution is slowly heated up and carries out 3 hours return stirrings by anhydrous acetic acid 0.69g.Reactant is cooled to room temperature, according to
It is secondary to be washed with saturated sodium bicarbonate aqueous solution 20ml and distilled water 20ml, then the organic layer of recycling is done with anhydrous magnesium sulfate
It is dry, solvent under reduced pressure is distilled, the product of gained is recrystallized with methanol 20ml, to obtain lurid initiator C-
1 (1- (9,9-H-7- nitrofluorene -2- bases)-acetophenone oxime-O- acetic acid esters) 1.22g.
Synthesis example 2:The synthesis of Photoepolymerizationinitiater initiater (C-2)
Reaction 1.
In a nitrogen atmosphere, fluorenes 200.0g, potassium hydroxide 268.8g and potassium iodide 19.9g is made to be dissolved in anhydrous dimethyl base sub-
Reactant is maintained 15 DEG C, was then slowly added to bromoethane 283.3g through 2 hours by sulfone 1L, and it is small that reactant is stirred at 15 DEG C to 1
When.Then after distilled water 2L is added into reactant and stirs 30 minutes, product is extracted with dichloromethane 2L, by having for extraction
After machine layer washs 2 times with distilled water 2L, the organic layer of recycling is dried with anhydrous magnesium sulfate, solvent under reduced pressure is distilled, by gained
Product fractional distillation under reduced pressure, to obtain (9, the 9- diethyls of lurid reactant 1 as highly viscous liquid
Base -9H- fluorenes) 248.6g.
Reaction 2.
So that reactant 1 (9,9- diethyl -9H- fluorenes) 100.5g is dissolved in dichloromethane 1L, reactant is cooled to -5 DEG C
Afterwards, it is slowly added to aluminium chloride 72.3g, is then passed through while preventing the temperature rise of reactant 2 hours and is slowly added to be diluted in
The propionyl chloride 50.1g of dichloromethane 50ml, and stir reactant 1 hour at -5 DEG C.Then, reactant is poured slowly into ice water
It in 1L and stirs 30 minutes after detaching organic layer, wash with distilled water 500ml, the organic layer of recycling is evaporated under reduced pressure, and general
The product of gained silica gel column chromatography (developing solvent；Ethyl acetate:N-hexane=1:4) it refines, to obtain as pale yellow
Reactant 2 (1- (9,9- diethyl -9H- fluorenes -2- bases) -1- acetone) 75.8g of the solid of color.
Reaction 3.
Reactant 2 (1- (9,9- diethyl -9H- fluorenes -2- bases) -1- acetone) 44.5g is set to be dissolved in tetrahydrofuran (THF)
900ml is sequentially added and is dissolved in Isosorbide-5-Nitrae-twoThe 4N HCl 150ml and isobutyl nitrite 24.7g of alkane, and reactant is existed
25 DEG C are stirred 6 hours.Then, ethyl acetate 500ml is added into reaction solution and stirs 30 minutes after detaching organic layer, uses
Distilled water 600ml washings, then the organic layer of recycling is dried with anhydrous magnesium sulfate, solvent under reduced pressure is distilled, use acetic acid second
Ester:Hexane (1:6) mixed solvent 300ml is dry after being recrystallized the solid product of gained, to obtain as shallow
Reactant 3 (1- (9,9- diethyl -9H- fluorenes -2- bases) -1,2- propanedione -2- oximes) 27.5g of the solid of grey.
Reaction 4.
In a nitrogen atmosphere, reactant 3 (1- (9,9- diethyl -9H- fluorenes -2- bases) -1,2- propanedione -2- oximes) is made to dissolve
In n-methyl-2-pyrrolidone (NMP) 1L, after reactant is maintained -5 DEG C, triethylamine 35.4g is added and stirs reaction solution
It mixes 30 minutes, then was slowly added to chloroacetic chloride 27.5g being dissolved in through 30 minutes molten made of n-methyl-2-pyrrolidone 75ml
Liquid stirs 30 minutes while preventing reactant from heating up.Then, distilled water 1L is poured slowly into reactant and stirs 30
Minute and after detaching organic layer, the organic layer of recycling is dried with anhydrous magnesium sulfate, solvent under reduced pressure is distilled.Using ethyl alcohol 1L,
It is dry after the solid product of gained is recrystallized, to obtain as grayish solid initiator C-2 (1- (9,
9- diethyl -9H- fluorenes -2- bases) -1,2- propanedione -2- oxime-O- acetic acid esters) 93.7g.
Production Example 1：The manufacture of colorant dispersion D-1
Using ball mill, using comprising 40 parts by weight as the C.I. paratoneres 254 represented by the chemical formula 3 of pigment, conduct
BYK2001 (the DISPERBYK of dispersant：Bi Ke (BYK) company manufactures, 45.1 weight % of solid component concentration) 24 parts by weight
The mixed liquor of (solid constituent convert about 10.8 parts by weight) and 136 parts by weight of methyl proxitol acetate as solvent carries out
Mixing in 12 hours and dispersion, to manufacture colorant dispersion D-1.
Production Example 2：The manufacture of colorant dispersion D-2
Using ball mill, by comprising the bromination diketopyrrolo-pyrrole represented by the chemical formula 2 as pigment, (BASF is public
Department3620 CF of Red S) 40 parts by weight, the BYK2001 (DISPERBYK as dispersant：Bi Ke (BYK)
Company manufactures, 45.1 weight % of solid component concentration) 24 parts by weight (solid constituent convert about 10.8 parts by weight) and as solvent
136 parts by weight of methyl proxitol acetate mixed liquor carry out 12 hours mixing and dispersion, to manufacture colorant dispersion
Liquid D-2.
Production Example 3：The manufacture of colorant dispersion D-3
Using ball mill, using comprising 40 parts by weight as the C.I. paratoneres 177 of pigment, as the BYK2001 of dispersant
(DISPERBYK：Bi Ke (BYK) company manufactures, 45.1 weight % of solid component concentration) (solid constituent converts about 24 parts by weight
10.8 parts by weight) and 136 parts by weight of methyl proxitol acetate as solvent mixed liquor carry out mixing in 12 hours and point
It dissipates, to manufacture colorant dispersion D-3.
Examples 1 to 8 and comparative example 1~8：The manufacture of red pixel photosensitive composition
Each ingredient is mixed according to the composition of following table 1, manufactures red pixel photosensitive composition (unit：
Weight %).
[table 1]
Alkali soluble resins (A)：SPCY-1L (Showa electrician company)
Photopolymerizable compound (B)：A9550 (company of the villages Xin Zhong)
Photoepolymerizationinitiater initiater (C)
C-1：The Photoepolymerizationinitiater initiater of synthesis example 1
C-2：The Photoepolymerizationinitiater initiater of synthesis example 2
C-3：I-369 (BASF)
C-4：OXE-01 (BASF)
Colorant dispersion (D)
D-1：The colorant dispersion of Production Example 1
D-2：The colorant dispersion of Production Example 2
D-3：The colorant dispersion of Production Example 3
Solvent (E)：Propylene glycol monomethyl ether
Additive (F)：Silicone based surfactants SH8400 (DOW CORNING Dong Li organosilicons company)
Experimental example 1
It is following to manufacture using the red pixel photosensitive composition manufactured in above-described embodiment and comparative example
Colour filter measures adaptation, development speckle and film-strength at this time, and the results are shown in following table 2 by the following method.
<The manufacture of colour filter>
It is placed on after being coated with red pixel on the glass substrate with photosensitive composition using spin-coating method
In heating plate, is maintained 3 minutes at a temperature of 100 DEG C and form colored layer film.Then, place with 1~50 μm line/
The experiment photomask of gap pattern, and 250 μm of irradiation ultraviolet lights will be set as with the interval of experiment photomask.At this point, ultraviolet light source
Using the high-pressure sodium lamp of the 1kW simultaneously comprising g, h, i line, with 50mJ/cm2Illumination be irradiated, not use special light
Learn filter.The colored layer film for having irradiated ultraviolet light is impregnated 2 minutes in the KOH aqueous development solution of pH10.5 and is carried out
Development.The glass substrate of the colored layer film after being formed with development is washed using distilled water, is then dried in a nitrogen atmosphere,
It is heated in 200 DEG C of heated oven 1 hour and carries out heat cure, to manufacture colour filter.
(1) adaptation
The pattern generated by optical microphotograph sem observation evaluates the peeling phenomenon of 20 μm of patterns according to following evaluation criteria
Degree.
<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) develop speckle
The pixel portion obtained after developing procedure is observed under Na lamps, counts the number of the pattern without the speckle that develops, and is pressed
It is evaluated according to following evaluation criteria.
<Evaluation criteria>
○：Do not develop speckle pattern be 4 or more
△：Do not develop speckle pattern be 1~3
×：There is no the patterns of no development speckle
(3) hardness
According to the test method(s) of JIS-K-5400, the hardness of film (be heating and curing film) is measured.Using pencil hardness tester,
When applying the load of 9.8N to the film that is heating and curing, the highest hardness that defect is not generated on film is set as hardness.As right
It is " Mitsubishi HI-UNI " according to the pencil used.
<Evaluation criteria>
◎：6H or more
○：4H~5H
△：2H~3H
×：1H or less
[table 2]
| Adaptation | Develop speckle | Hardness | |
| Comparative example 1 | △ | X | △ |
| Comparative example 2 | △ | X | △ |
| Comparative example 3 | △ | X | ○ |
| Comparative example 4 | X | X | X |
| Comparative example 5 | △ | △ | ○ |
| Comparative example 6 | X | △ | △ |
| Comparative example 7 | △ | △ | ○ |
| Comparative example 8 | X | △ | △ |
| Embodiment 1 | ○ | ○ | ◎ |
| Embodiment 2 | ○ | ○ | ◎ |
| Embodiment 3 | ○ | ○ | ◎ |
| Embodiment 4 | ○ | ○ | ◎ |
| Embodiment 5 | ○ | ○ | ◎ |
| Embodiment 6 | ○ | ○ | ◎ |
| Embodiment 7 | ○ | ○ | ◎ |
| Embodiment 8 | ○ | ○ | ◎ |
As shown in Table 2 above, it can confirm oxime ester fluorenes system's Photoepolymerizationinitiater initiater of the specific structure comprising the present invention and include
Red pixel coloring phototonus resin combination of the bromination diketopyrrolo-pyrrole compound as the Examples 1 to 8 of colorant
Object and any one of the oxime ester fluorenes system's Photoepolymerizationinitiater initiater and bromination diketopyrrolo-pyrrole compound for not including specific structure
The red pixel of comparative example 1~8 compared with photosensitive composition, adaptation and hardness are better, and inhibit aobvious
Shadow speckle occurs.
The specific part that the present invention has been described in detail above, for general technical staff of the technical field of the invention
For, it is obvious that such specific technology is preferred embodiment, and the scope of the present invention is not limited to this.As long as
General technical staff of the technical field of the invention can then be based on the above and carry out within the scope of the present invention respectively
Kind application and deformation.
Therefore, the actual scope of the present invention by subsidiary claim and and its equivalent define.
Claims (8)
1. a kind of red pixel photosensitive composition, it includes alkali soluble resins, photopolymerizable compound, light are poly-
Initiator, colorant and solvent are closed,
The Photoepolymerizationinitiater initiater includes the compound represented by following chemical formula 1,
The colorant includes the compound represented by following chemical formula 2,
Chemical formula 1
Chemical formula 2
In the formula,
R1~R3It is each independently hydrogen, halogen, C1-C20Alkyl, aryl, C1-C20Alkoxy, aralkyl, C1-C20Hydroxyl
Base alkyl, C2-C40Hydroxy alkoxy alkyl or C3-C20Naphthenic base；
R4~R10It is each independently hydrogen, C1-C20Alkyl, aryl, C1-C20Alkoxy, aralkyl, C1-C20Hydroxyl alkane
Base, C2-C40Hydroxy alkoxy alkyl, C3-C20Naphthenic base, amino, nitro, cyano or hydroxyl；
P is 0 or 1.
2. red pixel photosensitive composition according to claim 1, R1~R3Be each independently hydrogen,
C1-C6Alkyl or phenyl, R4~R10It is each independently hydrogen or nitro, p 0.
3. red pixel photosensitive composition according to claim 1, R1~R3Be each independently hydrogen or
C1-C6Alkyl, R4~R10For hydrogen, p 1.
4. red pixel photosensitive composition according to claim 1 is coloured relative to red pixel
The whole 100 weight % of solid constituent in photosensitive polymer combination, the content of the Photoepolymerizationinitiater initiater is 0.1~30 weight
Measure %.
5. red pixel photosensitive composition according to claim 1, the colorant further include
Compound represented by following chemical formula 3 and C.I. paratoneres 177,
Chemical formula 3
6. red pixel photosensitive composition according to claim 1, relative to whole 100 weights of colorant
% is measured, the content of the compound represented by the chemical formula 2 is 5~60 weight %.
7. a kind of colour filter utilizes the red pixel coloring phototonus resin combination described in any one of claim 1~6
Object and formed.
8. a kind of image display device, which is characterized in that have the colour filter described in claim 7.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2017-0034056 | 2017-03-17 | ||
| KR1020170034056A KR102033415B1 (en) | 2017-03-17 | 2017-03-17 | Colored Photosensitive Resin Composition for Red Pixel, Color Filter and Display Device |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108628099A true CN108628099A (en) | 2018-10-09 |
| CN108628099B CN108628099B (en) | 2021-05-04 |
Family
ID=63706191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201810201456.2A Active CN108628099B (en) | 2017-03-17 | 2018-03-12 | Colored photosensitive resin composition for red pixel, color filter and application thereof |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR102033415B1 (en) |
| CN (1) | CN108628099B (en) |
Citations (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009144115A1 (en) * | 2008-05-28 | 2009-12-03 | Basf Se | Improved, red colour filter composition |
| CN101827897A (en) * | 2007-10-17 | 2010-09-08 | 科莱恩金融(Bvi)有限公司 | The diketopyrrolopyrrolepigment pigment composition that is used for colour filter |
| CN102146217A (en) * | 2010-01-28 | 2011-08-10 | 富士胶片株式会社 | Pigment particle dispersion, light-cured composition and novel compound used in the dispersion |
| CN103339536A (en) * | 2011-01-28 | 2013-10-02 | 东洋油墨Sc控股株式会社 | Diketopyrrolopyrrole-type pigment composition for color filters, colored composition for color filters, and color filter |
| JP2014182253A (en) * | 2013-03-19 | 2014-09-29 | Toppan Printing Co Ltd | Black photosensitive resin composition, color filter and liquid crystal display device |
| CN104166309A (en) * | 2013-05-16 | 2014-11-26 | 奇美实业股份有限公司 | red photosensitive resin composition for color filter and application thereof |
| JP2015011095A (en) * | 2013-06-27 | 2015-01-19 | 凸版印刷株式会社 | Photosensitive resin composition for forming photospacer and color filter |
| JP2015045686A (en) * | 2013-08-27 | 2015-03-12 | 凸版印刷株式会社 | Photosensitive resin composition, color filter, and liquid crystal display device |
| CN104423148A (en) * | 2013-08-22 | 2015-03-18 | 东友精细化工有限公司 | A color photosensitive resin composition, color filter and display device comprising the same |
| CN104661997A (en) * | 2012-05-03 | 2015-05-27 | 韩国化学研究院 | Novel oximester fluorine compound, and photopolymerization initiator and photoresist composition comprising same |
| CN104678705A (en) * | 2013-12-02 | 2015-06-03 | 奇美实业股份有限公司 | Red photosensitive resin composition for color filter and application thereof |
| CN104684888A (en) * | 2012-09-28 | 2015-06-03 | 大东凯米克斯株式会社 | Fluorene-type compound, photopolymerization initiator comprising said fluorene-type compound, and photosensitive composition containing said photopolymerization initiator |
| CN104834181A (en) * | 2014-02-07 | 2015-08-12 | 东友精细化工有限公司 | Colored photosensitive resin composition, color filter comprising the same and display device |
| CN105093372A (en) * | 2014-05-13 | 2015-11-25 | Jsr株式会社 | Color filter, display device, red pixel, and green pixel |
| CN105278248A (en) * | 2014-07-24 | 2016-01-27 | 奇美实业股份有限公司 | Photosensitive resin composition, color filter and manufacturing method thereof, and liquid crystal display device |
| CN105378515A (en) * | 2013-07-15 | 2016-03-02 | 花王株式会社 | Pigment dispersion for color filter |
| CN105378513A (en) * | 2013-07-15 | 2016-03-02 | 花王株式会社 | Coloring composition for color filter |
| CN105652595A (en) * | 2014-12-02 | 2016-06-08 | 东友精细化工有限公司 | Black photosensitive resin composition, black matrix and image display device |
| CN105700293A (en) * | 2014-12-12 | 2016-06-22 | 东友精细化工有限公司 | Black photosensitive resin composition, black array and image display device comprising the same |
| CN105916837A (en) * | 2014-01-17 | 2016-08-31 | 三养社 | Novel beta-oximester fluorene compound, a photopolymerization initiator comprising same, and photoresist composition |
| KR20160109444A (en) * | 2015-03-11 | 2016-09-21 | 동우 화인켐 주식회사 | A colored photo sensitive resin composition, color filter and liquid crystal display device having the same |
| CN106483764A (en) * | 2015-08-27 | 2017-03-08 | 东京应化工业株式会社 | Photosensitive composite, pattern formation method, solidfied material and display device |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101904761B1 (en) | 2011-03-29 | 2018-10-08 | 토요잉크Sc홀딩스주식회사 | Red colored composition for color filter, and color filter |
| JP6248838B2 (en) * | 2013-07-22 | 2017-12-20 | Jsr株式会社 | Colored composition, colored cured film, display element and solid-state image sensor |
| KR102222404B1 (en) * | 2015-03-19 | 2021-03-03 | 동우 화인켐 주식회사 | Colored photosensitive resin composition for green or red pixel |
-
2017
- 2017-03-17 KR KR1020170034056A patent/KR102033415B1/en active IP Right Grant
-
2018
- 2018-03-12 CN CN201810201456.2A patent/CN108628099B/en active Active
Patent Citations (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101827897A (en) * | 2007-10-17 | 2010-09-08 | 科莱恩金融(Bvi)有限公司 | The diketopyrrolopyrrolepigment pigment composition that is used for colour filter |
| CN103436049A (en) * | 2007-10-17 | 2013-12-11 | 科莱恩金融(Bvi)有限公司 | Diketopyrrolopyrrole pigment composition for use in color filters |
| WO2009144115A1 (en) * | 2008-05-28 | 2009-12-03 | Basf Se | Improved, red colour filter composition |
| CN102146217A (en) * | 2010-01-28 | 2011-08-10 | 富士胶片株式会社 | Pigment particle dispersion, light-cured composition and novel compound used in the dispersion |
| CN103339536A (en) * | 2011-01-28 | 2013-10-02 | 东洋油墨Sc控股株式会社 | Diketopyrrolopyrrole-type pigment composition for color filters, colored composition for color filters, and color filter |
| CN104661997A (en) * | 2012-05-03 | 2015-05-27 | 韩国化学研究院 | Novel oximester fluorine compound, and photopolymerization initiator and photoresist composition comprising same |
| CN104684888A (en) * | 2012-09-28 | 2015-06-03 | 大东凯米克斯株式会社 | Fluorene-type compound, photopolymerization initiator comprising said fluorene-type compound, and photosensitive composition containing said photopolymerization initiator |
| JP2014182253A (en) * | 2013-03-19 | 2014-09-29 | Toppan Printing Co Ltd | Black photosensitive resin composition, color filter and liquid crystal display device |
| CN104166309A (en) * | 2013-05-16 | 2014-11-26 | 奇美实业股份有限公司 | red photosensitive resin composition for color filter and application thereof |
| JP2015011095A (en) * | 2013-06-27 | 2015-01-19 | 凸版印刷株式会社 | Photosensitive resin composition for forming photospacer and color filter |
| CN105378515A (en) * | 2013-07-15 | 2016-03-02 | 花王株式会社 | Pigment dispersion for color filter |
| CN105378513A (en) * | 2013-07-15 | 2016-03-02 | 花王株式会社 | Coloring composition for color filter |
| CN104423148A (en) * | 2013-08-22 | 2015-03-18 | 东友精细化工有限公司 | A color photosensitive resin composition, color filter and display device comprising the same |
| JP2015045686A (en) * | 2013-08-27 | 2015-03-12 | 凸版印刷株式会社 | Photosensitive resin composition, color filter, and liquid crystal display device |
| CN104678705A (en) * | 2013-12-02 | 2015-06-03 | 奇美实业股份有限公司 | Red photosensitive resin composition for color filter and application thereof |
| CN105916837A (en) * | 2014-01-17 | 2016-08-31 | 三养社 | Novel beta-oximester fluorene compound, a photopolymerization initiator comprising same, and photoresist composition |
| CN104834181A (en) * | 2014-02-07 | 2015-08-12 | 东友精细化工有限公司 | Colored photosensitive resin composition, color filter comprising the same and display device |
| CN105093372A (en) * | 2014-05-13 | 2015-11-25 | Jsr株式会社 | Color filter, display device, red pixel, and green pixel |
| CN105278248A (en) * | 2014-07-24 | 2016-01-27 | 奇美实业股份有限公司 | Photosensitive resin composition, color filter and manufacturing method thereof, and liquid crystal display device |
| CN105652595A (en) * | 2014-12-02 | 2016-06-08 | 东友精细化工有限公司 | Black photosensitive resin composition, black matrix and image display device |
| CN105700293A (en) * | 2014-12-12 | 2016-06-22 | 东友精细化工有限公司 | Black photosensitive resin composition, black array and image display device comprising the same |
| KR20160109444A (en) * | 2015-03-11 | 2016-09-21 | 동우 화인켐 주식회사 | A colored photo sensitive resin composition, color filter and liquid crystal display device having the same |
| CN106483764A (en) * | 2015-08-27 | 2017-03-08 | 东京应化工业株式会社 | Photosensitive composite, pattern formation method, solidfied material and display device |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20180106235A (en) | 2018-10-01 |
| CN108628099B (en) | 2021-05-04 |
| KR102033415B1 (en) | 2019-10-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104049460B (en) | Photosensitive composition | |
| CN106842818A (en) | Photosensitive composition, the colour filter and image display device that are manufactured using it | |
| CN112904672A (en) | Colored photosensitive resin composition suitable for columnar spacer and black matrix | |
| CN106909027A (en) | Photosensitive composition, colour filter and its preparation method, image display device | |
| CN104423148A (en) | A color photosensitive resin composition, color filter and display device comprising the same | |
| CN104834181A (en) | Colored photosensitive resin composition, color filter comprising the same and display device | |
| CN107239003A (en) | Photosensitive composition, colour filter and image display device | |
| CN106980231A (en) | Red sensitive resin combination, the colour filter manufactured using it and the display device with the colour filter | |
| CN104914667B (en) | Colour filter photosensitive composition, colour filter and the liquid crystal display device for having it | |
| CN107229186A (en) | Photosensitive composition, the colour filter comprising it and display device | |
| CN103509151A (en) | Alkali soluble resin and photosensitive resin composition containing the same | |
| CN106918992A (en) | Green photonasty resin composition, the colour filter comprising it and display device | |
| CN103969950A (en) | Colored Photopolymer Composition | |
| CN110446977A (en) | Blue-sensitive resin combination, the colour filter and image display device manufactured using the composition | |
| CN107621750A (en) | Photosensitive composition, the colour filter and image display device manufactured using said composition | |
| CN103543605A (en) | Colored photosensitive resin composition and color filter using the same | |
| CN104345560A (en) | colored photosensitive resin composition, color filter, and liquid crystal display device having the color filter | |
| CN105759567A (en) | Coloring photosensitive resin composition, colorful optical filter, and image display device | |
| TW201902945A (en) | Colored photosensitive resin composition and light shielding spacer prepared therefrom | |
| CN108062002A (en) | Photosensitive composition, colour filter and image display device | |
| CN103576461A (en) | Photosensitive resin composition, colored filter, liquid crystal display device and imaging element | |
| CN108535957A (en) | Photosensitive composition, colour filter and image display device | |
| CN108628099A (en) | Red pixel photosensitive composition, colour filter and its application | |
| CN108333867A (en) | Photosensitive composition, colour filter and image display device | |
| CN104423150A (en) | Photosensitive resin composition, color filter and liquid crystal display device using the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |