CN107239004A - Photosensitive composition, the colour filter and image display device manufactured using it - Google Patents
Photosensitive composition, the colour filter and image display device manufactured using it Download PDFInfo
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- CN107239004A CN107239004A CN201710016692.2A CN201710016692A CN107239004A CN 107239004 A CN107239004 A CN 107239004A CN 201710016692 A CN201710016692 A CN 201710016692A CN 107239004 A CN107239004 A CN 107239004A
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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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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B41/00—Special methods of performing the coupling reaction
- C09B41/001—Special methods of performing the coupling reaction characterised by the coupling medium
- C09B41/005—Special methods of performing the coupling reaction characterised by the coupling medium containing low molecular weight dispersing agents; containing surface active polythylene gylcols
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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
- 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
- G03F7/0048—Photosensitive materials characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents
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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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- 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
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- Nonlinear Science (AREA)
- Optics & Photonics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
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Abstract
The present invention relates to photosensitive composition, in particular it relates to which photosensitive composition, the colour filter and image display device that are manufactured using it, the photosensitive composition are included：Include the rhodamine based dye existed with particle state and the colouring agent of pigment；With the dispersant for including triazine based compound.
Description
Technical field
The colour filter and image display device manufactured the present invention relates to photosensitive composition, using it.
Background technology
Colour filter is widely used in the various display devices such as photographing element, liquid crystal display device (LCD), and its application is in urgency
Expand fastly.Above-mentioned colour filter by red (Red), green (Green) and blueness (Blue) three kinds of colors colored pattern group
Into, or the colored pattern of three kinds of colors by yellow (Yellow), magenta (Magenta) and cyan (Cyan) constitutes.
Widely used colour filter, is generally manufactured by the following in above-mentioned display device：Foring black matrix pattern
Spin coating or slot coated are used on substrate by the colored photosensitive of the pigment dispensing composition of the color containing equivalent to each pattern
After property resin combination is equably coated with, film formed by heat drying is exposed and developed, is chased after as needed
Plus be heating and curing, each color is repeated aforesaid operations, so that the pixel of colors is formed, in addition, even in not being
Ink-jet method and print process of above-mentioned coating method etc. are not needed in the process of developing procedure, are used yet and are used in coloured material
The photosensitive composition manufacture colour filter of above-mentioned pigment dispensing composition.
Colour filter for having used above-mentioned such photosensitive composition, it is desirable to high brightness, high-contrast
Etc. physical property, in addition, needing the high pixel of color reproduction recently.Thus, the coloured material used in above-mentioned colored resin composition
Pigment and carbon black content rise.But, in the case where the content of colored resin composition intrinsic color material is improved, have
Following the problem of：In order to show excellent optical characteristics, it is necessary to make pigment particle, high concentration pigment discrete sets are particularly manufactured
Viscosity is raised during compound, or pigment dispensing composition bin stability such as gelation in storage is deteriorated, and thus also makes brightness
With the reduction of the optical characteristics such as contrast.
Japanese Unexamined Patent Publication 2013-61619 is related to colour filter cyan colorant composition and has used its colour filter base
Plate, discloses the content for being related to colour filter cyan colorant composition, and it is at least to contain colouring agent, resin glue, height
The colour filter of dispersal agent molecule and solvent cyan colorant composition, it is characterised in that if above-mentioned colouring agent contain pigment and
Red bright based dye, above-mentioned rhodamine based dye exists with particle state in above-mentioned cyan colorant composition, and actual conditions are
Dispersion stabilization is not excellent, and contrast is slightly difficult to be applied to high-quality colour filter.
Accordingly, it would be desirable to develop, various dispersion stabilizations are excellent, can manufacture the high-quality colour filter with high-contrast
Photosensitive composition.
Prior art literature
Patent document 1：Japanese Unexamined Patent Publication 2013-61619 publications (2013.04.04)
The content of the invention
The invention problem to be solved
It is an object of the invention to provide dispersion stabilization is excellent or can manufacture developability, heat resistance, solvent resistant
The photosensitive composition of property, contrast or the excellent colour filter of brightness.
In addition, the present invention to provide the colour filter manufactured using above-mentioned photosensitive composition and image is shown
Device.
Means for solving the problems
Photosensitive composition of the present invention for realizing above-mentioned purpose, it is characterised in that include：With
The rhodamine based dye that particle state is present；Include the dispersant of triazine based compound；And pigment.
In addition, the present invention provides the colour filter that is manufactured with above-mentioned photosensitive composition and the image comprising it
Display device.
The effect of invention
The photosensitive composition of the present invention can provide dispersion stabilization excellent coloring phototonus resin group
Compound.
In addition, with the colour filter that manufactures of photosensitive composition of the present invention and the image display device comprising it
Have the advantages that developability, heat resistance, solvent resistance, contrast or brightness are excellent.
Embodiment
The present invention is explained below.
In the present invention, certain component be located at other components " on " when, its feelings not only connected comprising certain component with other components
Shape, is also contained in the situation that also there are other components between two components.
In the present invention, during certain part "comprising" inscape, as long as being recorded without especially opposite, itself and it is non-excluded other
Inscape, but be meant to also comprising other inscapes.
＜ photosensitive compositions ＞
The scheme of the present invention is related to photosensitive composition, and it is included：If including what is existed with particle state
The colouring agent of red bright based dye and pigment；With the dispersant for including triazine based compound.In one embodiment, the present invention relates to green grass or young crops
Chromatic colorant photosensitive polymer combination, it is included：Include the rhodamine based dye existed with particle state and the colouring agent of pigment；
With the dispersant for including triazine based compound.
Colouring agent of the present invention includes the rhodamine based dye and pigment existed with particle state.
Rhodamine based dye
Photosensitive composition of the present invention includes the rhodamine based dye existed with particle state.
In one embodiment of the present invention, above-mentioned rhodamine based dye can include selected from C.I. acid reds 52,87,91,
92、94、289；C.I. Indian yellow 73；C.I. alkali red 1:1；C.I. alkaline purple 10,11；With more than a kind in C.I. solvent red 49s.
Photosensitive composition of the present invention due to comprising the rhodamine based dye existed with particle state,
Therefore in the case where having manufactured colour filter, the pixel with filter substrate, particularly cyan pixel have high-contrast
Advantage.
It is undesirable theoretically to be limited, but for having used the filter substrate of general dyestuff, due to dye
Material dissolves in the composition, therefore dries cohesion during due to freely bakeing, and can occur purple when reduction, the exposure of contrast
Decomposition, distillation of dye molecule when reducing, bakeing afterwards of contrast etc. is drawn caused by the oxidation of dye molecule caused by outside line
Reduction of contrast risen etc..
But, in the present invention, because above-mentioned rhodamine based dye exists with particle state, therefore in coating, dry, exposure
Above-mentioned rhodamine based dye is also maintained so that particle state is stable after light, development, rear baking, therefore the pixel with colour filter, spy
It is not the excellent advantage of the contrast of cyan pixel.
Above-mentioned rhodamine based dye can be insoluble in as the propylene glycol monomethyl ether of ester series solvent (PMA)
Property.Above-mentioned PMA is excellent due to the dispersion stabilization of stability, coating, drying property, pigment, therefore is to use pigment
Photosensitive composition in widely used solvent, above-mentioned rhodamine based dye is insoluble in above-mentioned PMA
In the case of, in the case where not damaging above-mentioned characteristic, pigment described later and above-mentioned rhodamine based dye can be in above-mentioned PMA
Stably exist with particle state, therefore preferably.
For above-mentioned rhodamine based dye, it is preferred to use it is refined will be contained ionic miscellaneous in above-mentioned rhodamine based dye
Matter is removed.For example, it is preferable to make Na contained in above-mentioned rhodamine based dye+、Cl-、SO4 2-Such ionic impurity sum turns into
Below 20000ppm, more preferably as below 10000ppm.Contained Na in above-mentioned rhodamine based dye+、Cl-、SO4 2-It is such
In the case that ionic impurity sum meets below 20000ppm, with can prevent in above-mentioned PMA due to ionic impurity
And make the advantage of the phenomenon of dispersion stabilization reduction.
As long as the process for purification method usually used in this field of above-mentioned rhodamine based dye, then be not limited to
This, can for example use reprecipitation method, recrystallization method, reverse osmosis membrane or using ion exchange resin (cationic ion-exchange resin,
Anion exchange resin) the method such as ion exchange.
Whether above-mentioned rhodamine based dye exists in above-mentioned photosensitive composition with particle state
State, can use grain size analysis machine (Particle size analyzer, accusizer780A) to confirm.
With in the colour filter that manufactures of photosensitive composition of the present invention, in order to investigate above-mentioned rhodamine based dye
Whether it is particle state or whether is molecular state, for example, can be for example following by FIB-TEM analyses and EDX elementary analyses
Cyan pixel like that to colour filter judges.The colour filter of above-mentioned manufacture is due to pigment particles and above-mentioned rhodamine based dye
Particle mixes, thus for their particle 100 analyze.The particle diameter of above-mentioned pigment and above-mentioned rhodamine based dye
Due to for 10~500nm, therefore FIB-TEM measure diameter is set to 1~10nm.After FIB-TEM observations, by EDX to seeing
Examine portion and carry out elementary analysis.If to the EDX analysis results and the EDX of above-mentioned rhodamine based dye itself of above-mentioned 100, particle
Analysis result is compared, and the consistent particle of analysis result then can interpolate that in the colour filter of manufacture if 1~100
State whether rhodamine based dye exists with particle state.
On the other hand, whether above-mentioned rhodamine based dye is contained in above-mentioned photosensitive composition, for example, energy
Enough judged using LR laser raman optical spectroscopy.That is, carry out the coating of above-mentioned photosensitive composition, solvent seasoning,
Exposure, development, rear bakee make pixel.LR laser raman spectrophotometric spectra and above-mentioned rhodamine system by the pixel to so manufacturing
The LR laser raman spectrophotometric spectra of dyestuff itself is compared, so as to judge to be in above-mentioned photosensitive composition
It is no to contain above-mentioned rhodamine based dye.
The average grain diameter of above-mentioned rhodamine based dye and pigment described later is preferably 30~200nm, more preferably 30~
100nm.In the case that the average grain diameter of above-mentioned rhodamine based dye is more than 200nm, due to the scattering of particle, sometimes transmissivity and
Contrast is slightly reduced, in the case that the average grain diameter of above-mentioned rhodamine based dye is less than 30nm, the binding agent in unexposed portion
The alkali-solubility of resin is slightly reduced, and pattern processability is slightly reduced sometimes.
By for above-mentioned rhodamine based dye and pigment, using dispersion machines such as sand mill, ball mills, utilizing zirconium oxide bead
Grain applies shear stress, so as to by the average grain diameter of above-mentioned rhodamine based dye and pigment regulation to above range.
But, under the dispersion condition of previously known pigment, the average grain diameter of above-mentioned rhodamine based dye is adjusted sometimes
Save slightly difficult in above range.In a word, for above-mentioned powder pigment, be configured to 30nm or so 1 particle assembly and
Form several μm of powder particle.Above-mentioned powder pigment is small due to the cohesiveness between 1 particle, therefore is cut with weaker
Shearing stress is dismissed by the scattered cohesion for just making 1 particle of short time, and average grain diameter can be made to turn into 30~200nm.But,
For dyestuff powder, 1nm or so elements collection is formed by several μm of oversize grain.Dyestuff powder is due between molecule
Cohesiveness is strong, therefore makes average grain diameter slightly difficulty smaller than 200nm with weak shear stress.Further, since not deposited in dyestuff
In 1 particle, so if enhancing shear stress or extension jitter time, then can make average particle diameter became smaller than 30nm.
Therefore, in the present invention, in order that the average grain diameter of above-mentioned rhodamine based dye and pigment turns into 30~200nm, it is excellent
It is selected under dispersion condition different from each other and is disperseed.
As the dispersion condition of above-mentioned rhodamine based dye, the zirconium oxide bead of 0.3~2.0 μm of bead granular diameter is preferably used
Grain, with strong shear stress, it is 3~10 hours/kg to make jitter time, as the dispersion condition of above-mentioned pigment, preferably uses pearl
The zirconium oxide bead of 0.1~2.0 μm of particle diameter of grain, it is 1~10 hour/kg to make jitter time.
In the present invention, the above-mentioned rhodamine based dye dispersion liquid and above-mentioned pigment of independent dispersion process will preferably have passed through
After dispersion liquid mixing, by the process further disperseed., can be by above-mentioned rhodamine based dye and pigment by the process
Average grain diameter regulation to 30~100nm scope, can further improve transmissivity and contrast.
As the addition dispersion condition of above-mentioned mixed dispersion liquid, the zirconium oxide of 0.01~0.2 μm of bead granular diameter is preferably used
Bead, with weak shear stress, it is 0.1~3 hour/kg to make jitter time.
If in addition, the photosensitive composition of the present invention is simultaneously included in dispersion stability in above-mentioned composition
Red bright based dye and the dispersant for including triazine based compound, compared with the individually situation comprising rhodamine based dye, with energy
The advantage for enough making the problem of contrast is reduced further improve.
Above-mentioned rhodamine based dye, relative to all 100 parts by weight of above-mentioned colorant dispersion, can include 1~80 weight
Measure part, preferably 2~50 parts by weight.In the case of containing above-mentioned rhodamine based dye within the above range, in dispersion stabilization
Aspect with transmissivity is preferred.In the case of containing above-mentioned rhodamine based dye less than 1 parts by weight, transmissivity slightly has drop sometimes
It is low, more than 80 parts by weight in the case of, due to the cohesion of dyestuff, dispersion stabilization slightly has reduction sometimes.
Include the dispersant of triazine based compound
Photosensitive composition of the present invention is included：Include the dispersant of triazine based compound.Above-mentioned three
As long as then it is not limited to this as material known to dispersant in the piperazine based compound field.For example, Japan can be used
Triazine system dispersant described in JP 2008-214515, Japanese Unexamined Patent Publication 2011-032374.
In another embodiment of the present invention, as above-mentioned triazine based compound, the change represented by following chemical formula 1 is included
Compound.
[chemical formula 1]
In chemical formula 1,
R is hydrogen atom, the alkyl of carbon number 1~20, the straight-chain of carbon number 1~20 or the alkoxy of branch's chain state or-NR1R2
Base,
R1 and R2 are each independently the alkyl of hydrogen atom or carbon number 1~20,
Now, abovementioned alkyl and alkoxy are replaced by the alkoxy of the straight-chain or branch's chain state of hydroxyl or carbon number 1~20
Or it is unsubstituted.
Now, as the alkyl of carbon number 1~20, methyl, ethyl, n-propyl, isopropyl, Zhong Bingji, positive fourth can be included
The alkyl of the carbon number 1~20 of the straight-chains such as base, isobutyl group, sec-butyl, the tert-butyl group or branch's chain state.
In addition, as the alkoxy of carbon number 1~20, methoxyl group can be included, ethyoxyl, positive propoxy, isopropoxy, secondary
The alcoxyl of the carbon number 1~20 of the straight-chains such as propoxyl group, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy or branch's chain state
Base.
Dispersant of the present invention includes the triazine based compound represented by above-mentioned chemical formula 1, can be in various media
In be uniformly dispersed pigment and above-mentioned rhodamine based dye.Therefore, the colored photosensitive of the triazine based compound comprising the present invention
Property the rising that re-unites with viscosity of the resin combination due to suppressing pigment and above-mentioned rhodamine based dye, therefore with good
Bin stability.
In addition, in dispersant above-mentioned triazine based compound and resin type dispersant and in the case of using, improve pigment and
The effect that the dispersed effect of above-mentioned rhodamine based dye and suppression are re-united can become particularly significant.
In addition, the triazine based compound represented by the above-mentioned chemical formula 1 of the present invention in visibility region due to showing white,
Therefore can be made using the colour filter that is formed by the photosensitive composition comprising above-mentioned triazine based compound can be with
Carry out the colour liquid crystal display device of the colour developing of high brightness.Coloring phototonus resin of the above-mentioned triazine based compound due to having used it
The initial viscosity of composition suppresses the effect re-united the height of pigment in addition than relatively low, therefore the storage with dispersant is stable
Property it is excellent, storage caused by viscosity the less feature of increase ratio.
In another embodiment of the present invention, for above-mentioned triazine based compound, relative to above-mentioned colouring agent entirety 100
Parts by weight, can contain 0.1~60 parts by weight.In the case of containing above-mentioned triazine based compound within the above range, due to energy
Enough suppress the crystalline growth of above-mentioned rhodamine based dye and above-mentioned pigment, therefore preferably.Relative to above-mentioned colouring agent, with less than
In the case that 0.1 parts by weight contain above-mentioned triazine based compound, the phenomenon of above-mentioned rhodamine based dye cohesion can be made, with
In the case of containing more than 60 parts by weight, contrast is slightly reduced sometimes.
Colouring agent
Colouring agent of the present invention can include more than a kind of above-mentioned rhodamine based dye, include more than a kind pigment
With above-mentioned pigment dispersing agent.Above-mentioned rhodamine based dye can be applicable above-mentioned content.
Above-mentioned pigment can use the organic pigment or inorganic pigment typically used in the field.Above-mentioned pigment can be used
The various pigment used in printing-ink, jetted ink etc., specifically, can include water-soluble azo pigment, insoluble idol
Nitrogen pigment, phthalocyanine color, quinacridone pigment, isoindolenone pigments, isoindoline pigment, perylene dye, perylene ketone pigment, bis- Evil
Piperazine pigment, anthraquinone pigment, dianthraquinone pigment, anthracene pyrimidine pigment, anthrone (anthanthrone) pigment, indanthrone
(indanthrone) pigment, yellow anthrone pigment, pyranthrone (pyranthrone) pigment, diketo-pyrrolo pyrrole pigments etc..
As above-mentioned inorganic pigment, the metallic compounds such as metal oxide, metallic complex salt can be included, specifically, can be arranged
Enumerate oxide or metal composite oxide of the metals such as iron, cobalt, aluminium, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony, carbon black etc..It is special
Not, as above-mentioned organic pigment and inorganic pigment, specifically, colour index (The society of Dyers can be included
And Colourists publish) in be categorized as the compound of pigment, more specifically, following colour index (C.I.) sequence can be included
Number pigment, but these may not be defined in.
C.I. pigment yellow 13,20,24,31,53,83,86,93,94,109,110,117,125,137,138,139,147,
148th, 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
C.I. Pigment Red 9,97,105,122,123,144,149,166,168,176,177,180,192,215,216,
224th, 242,254,255 and 264
C.I. pigment violet 14,19,23,29,32,33,36,37 and 38
C.I. pigment blue 15 (15：3、15：4、15：6 etc.), 21,28,60,64 and 76
C.I. pigment Green 7,10,15,25,36,47,58,59,62 and 63
C.I. pigment brown 28
C.I. pigment black 1 and 7 etc.
Above-mentioned pigment can each be used alone or two or more is applied in combination.
In foregoing illustrative C.I. pigment, can be preferably used selected from C.I. pigment oranges 38, C.I. pigment red 122s,
C.I. paratonere 166, C.I. paratoneres 177, C.I. paratoneres 208, C.I. paratoneres 242, C.I. paratoneres 254, C.I. face
Expect red 255, C.I. pigment yellow 13s 8, C.I. pigment yellow 13s 9, C.I. pigment yellows 150, C.I. pigment yellows 185, C.I. pigment Green 7s,
C.I. pigment green 36, C.I. naphthol greens 58, C.I. pigment Violet 23s, C.I. pigment blue 15s：3rd, C.I. pigment blue 15s：Pigment in 6.
The colorant dispersion that above-mentioned pigment disperses with preferably using its uniform particle diameter.As for making the grain of above-mentioned pigment
One of the uniformly dispersing method in footpath, can include and method of decentralized processing etc. is carried out containing pigment dispersing agent, using this
Method, can obtain the colorant dispersion for the state that pigment is uniformly dispersed in the solution, therefore preferably.
, can be additionally further with the above-mentioned dispersant comprising triazine based compound for above-mentioned pigment dispersing agent
It is additional, the surfactant such as can include cation system, anion system, nonionic system, both sexes, Polyester, many amine systems
Deng these can each be used alone or two or more is applied in combination, but be not limited to this.
The content of above-mentioned pigment, is 1~50 parts by weight, preferably relative to all 100 parts by weight of above-mentioned colorant dispersion
The scope of the parts by weight of ground 5~40.If the content of above-mentioned pigment is glued according to the scope that above-mentioned benchmark is 1~50 parts by weight
Degree is low, and bin stability is excellent, and dispersion efficiency is high, and the rising to light dark ratio is effective, therefore preferably.
In addition, above-mentioned colorant dispersion can further include decentralized medium.
In order to maintain pigment de- cohesion and stability and add above-mentioned decentralized medium, without limitation use the neck
The decentralized medium typically used in domain.It can preferably contain and include BMA (butyl methacrylate) or DMAEMA (methacrylic acids
N, N- dimethylamino ethyl ester) acrylic ester dispersant (hereinafter referred to as dispersant containing acrylic).Now, aforesaid propylene acid
It is the scattered of the active control method manufacture that dispersant is preferably proposed using using in KR published patent 2004-0014311
Agent, as the commercially available product of the acrylic ester dispersant manufactured by above-mentioned active control method, can include DISPER BYK-
2000th, DISPER BYK-2001, DISPER BYK-2070, DISPER BYK-2150 etc..
Foregoing illustrative dispersant containing acrylic can each be used alone or two or more is applied in combination.
Above-mentioned decentralized medium can also use the pigment point of other resin types in addition to above-mentioned dispersant containing acrylic
Powder.As the pigment dispersing agent of other above-mentioned resin types, the pigment dispersing agent of known resin type can be included, is particularly gathered
Urethane, polyacrylate are the polycarboxylate of representative, unsaturated polyamide, polycarboxylic acids, (part) amine salt, the poly- carboxylic of polycarboxylic acids
Acid ammonium salt, the alkylamine salt of polycarboxylic acids, polysiloxanes, long-chain polyaminoamide phosphate, the polycarboxylic acids of hydroxyl ester with
And the reaction of their modification product or the polyester and poly- (rudimentary alkyleneimines) that pass through the carboxyl with free (free)
Oily dispersant as the acid amides of formation or their salt；(methyl) acrylic-styrene copolymer, (methyl) propylene
As acid-(methyl) acrylate copolymer, styrene-maleic acid copolymer, polyvinyl alcohol or PVP
Water-soluble resin or water-soluble polymeric compounds；Polyester；Modified polyacrylate；The addition life of ethylene oxide/propylene oxide
Into thing and phosphate etc..As the commercially available product of above-mentioned resin type dispersant, as cation system pitch dispersant, for example, it can arrange
Enumerate the trade name of BYK (PVC ッ Network) 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 AG：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 Lubirzol companies：SOLSPERS-24000、
SOLSPERS-32550、NBZ-4204/10；The trade name of Chuan Yan fine chemistries Co., Ltd.：ヒノアクト(HINOACT)T-
6000、ヒノアクトT-7000、ヒノアクトT-8000；The trade name of Ajincomoto Co., Inc：アジスパー
(AJISPUR)PB-821、アジスパーPB-822、アジスパーPB-823；The trade name of Kyoeisha Chemical Co., Ltd.：
フローレン(FLORENE)DOPA-17HF、フローレンDOPA-15BHF、フローレンDOPA-33、フローレ
Application DOPA-44 etc..In addition to aforesaid propylene acid system dispersant, the pigment dispersing agent of other resin types each can individually make
It is applied in combination, can also be used with dispersant containing acrylic and use with or by two or more.
Above-mentioned pigment dispersing agent, relative to all 100 weights of solid constituent of above-mentioned photosensitive composition
Part is measured, 0.1~30 parts by weight can be contained, preferably containing 0.1~15 parts by weight.The content of above-mentioned pigment dispersing agent is met
In the case of above-mentioned scope, it is possible to increase contrast and stability.
In other embodiments of the present invention, above-mentioned photosensitive composition, which can be included further, to be selected from
At least one in alkali soluble resin, photopolymerizable compound, Photoepolymerizationinitiater initiater and solvent.
Alkali soluble resin
Alkali soluble resin includes the ethylenically unsaturated monomer with carboxyl and is polymerized.It is for when forming pattern
Development treatment process in the alkaline developer that uses assign soluble composition.
Ethylenically unsaturated monomer with carboxyl is not particularly limited, can for example include acrylic acid, methacrylic acid,
The monocarboxylic acid class such as crotonic acid；The omega-dicarboxylic acids such as fumaric acid, mesaconic acid, itaconic acid and their acid anhydrides；ω-carboxy-polycaprolactone list
(methyl) acrylate etc. has list (methyl) esters of acrylic acid of the polymer of carboxyl and hydroxyl etc. in two ends, preferably may be used
Think acrylic acid and methacrylic acid.These can be used alone or are used in mixed way two or more.
Alkali soluble resin of the present invention can be further comprising can be with above-mentioned monomer copolymerization at least one kind of its
The product that his monomer is polymerized.Styrene can for example be included, it is vinyltoluene, methyl styrene, p- chlorostyrene, o-
Methoxy styrene, m- methoxy styrene, p-methoxystyrene, o- vinyl benzyl methyl ether, m- vinyl benzyl
Ylmethyl ether, p- vinyl benzyl methyl ether, o- vinylbenzyl glycidyl base ether, m- vinylbenzyl glycidyl
The aromatic ethenyl compounds such as base ether, p- vinylbenzyl glycidyl base ether；N- N-cyclohexylmaleimides, N- benzyls
The o- hydroxyphenyl-maleimides of maleimide, N-phenylmaleimide, N-, the m- hydroxyphenyl-maleimides of N-,
The p- hydroxyphenyl-maleimides of N-, N- ortho-methyls phenyl maleimide, the m- methylphenylmaleimides of N-, N- are p-
The o- methoxyphenyl maleimide of methylphenylmaleimide, N-, the m- methoxyphenyl maleimides of N-, N- are p-
The N- substituted maleimide amine compounds such as methoxyphenyl maleimide；(methyl) methyl acrylate, (methyl) acrylic acid
Ethyl ester, (methyl) n-propyl, (methyl) isopropyl acrylate, (methyl) n-butyl acrylate, (methyl) acrylic acid are different
(methyl) alkyl-acrylates such as butyl ester, (methyl) sec-butyl acrylate, (methyl) tert-butyl acrylate；(methyl) acrylic acid
Ring pentyl ester, (methyl) cyclohexyl acrylate, (methyl) acrylic acid 2- methyl cyclohexyls, the bicyclic amoxy second of (methyl) acrylic acid 2-
Alicyclic (methyl) esters of acrylic acid such as ester, (methyl) isobornyl acrylate；(methyl) phenyl acrylate, (methyl) acrylic acid
Benzyl ester etc. (methyl) benzyl acrylate class；3- (methacryloxymethyl) oxetanes, 3- (methacryloxies
Methyl) -3- Ethyloxetanes, 3- (methacryloxymethyl) -2- trifluoromethyls oxetanes, 3- (methyl-props
Alkene pivaloyloxymethyl) -2- phenyl oxetanes, 2- (methacryloxymethyl) oxetanes, 2- (methacryls
Epoxide methyl) the unsaturated oxetane compound such as -4- trifluoromethyl oxetanes etc..These can be used alone or
Two or more is used in mixed way.
In this specification, (methyl) acrylate means acrylate or methacrylate.
Content to alkali soluble resin of the present invention is not particularly limited, for example, relative to coloring phototonus tree
All 100 parts by weight of solid constituent in oil/fat composition, preferably comprise 5~80 parts by weight, further preferably 10~70 parts by weight.
The content of above-mentioned alkali soluble resin be above range within the case of, due in developer solution dissolubility fully, therefore
The film that pattern forms the pixel portion that exposure portion is easily prevented during development is reduced, and the deciduous of non-pixel portion can become good.
Photopolymerizable compound
The photopolymerizable compound contained in the photosensitive composition of the present invention is poly- in light and light described later
The compound that can polymerize in the presence of initiator is closed, monofunctional monomer, 2 functional monomers, other polyfunctional monomers can be included
Deng.
Species to above-mentioned monofunctional monomer is not particularly limited, for example, can include nonyl phenyl carbitol acrylic acid
Ester, acrylic acid 2- hydroxyl -3- phenoxy-propyls, 2- ethylhexyl carbitols acrylate, acrylic acid 2- hydroxy methacrylates, N- ethene
Base pyrrolidones etc..
Species to above-mentioned 2 functional monomer is not particularly limited, for example, can include 1,6- hexylene glycols two (methyl) propylene
Acid esters, ethylene glycol two (methyl) acrylate, neopentyl glycol two (methyl) acrylate, triethylene glycol two (methyl) acrylate,
Double (acryloyl-oxyethyl) ether, 3- methyl pentanediols two (methyl) acrylate of bisphenol-A etc..
Species to above-mentioned polyfunctional monomer is not particularly limited, for example, can include trimethylolpropane tris (methyl) third
Olefin(e) acid ester, ethoxylated trimethylolpropane three (methyl) acrylate, propoxylation trimethylolpropane tris (methyl) propylene
Acid esters, pentaerythrite three (methyl) acrylate, pentaerythrite four (methyl) acrylate, dipentaerythritol three (methyl) propylene
Acid esters, dipentaerythritol five (methyl) acrylate, ethoxylated dipentaerythritol six (methyl) acrylate, propoxylation two
Pentaerythrite six (methyl) acrylate, dipentaerythritol six (methyl) acrylate etc..
Relative to all 100 parts by weight of solid constituent of photosensitive composition, 5~50 parts by weight are preferably comprised
Above-mentioned photopolymerizable compound, further preferably 7~48 parts by weight.If the content of photopolymerizable compound is in above-mentioned model
Within enclosing, then the intensity of pixel portion, flatness can become good.
Photoepolymerizationinitiater initiater
To the Photoepolymerizationinitiater initiater that contains in the photosensitive composition of the present invention and unrestricted, for selected from triazine
More than a kind of compound in based compound, acetophenone based compound, bisglyoxaline based compound and oxime compound.Containing above-mentioned
The photosensitive polymer combination of Photoepolymerizationinitiater initiater is high sensitivity, should for the pixel (pixel) using said composition formation
The intensity of pixel portion, pattern become good.
In addition, if photopolymerization initiation adjuvant is used in combination in Photoepolymerizationinitiater initiater, then the photonasty tree containing them
Oil/fat composition further turns into high sensitivity, is provided using productivity ratio during said composition formation colour filter, therefore preferably.
As triazine based compound, for example, it can include double (the trichloromethyl) -6- (4- methoxyphenyls) -1,3,5- of 2,4-
Double (trichloromethyl) -6- (4- methoxyl groups the naphthyl) -1,3,5- triazines of triazine, 2,4-, double (the trichloromethyl) -6- piperonyls of 2,4- -
Double (trichloromethyl) -6- (4- the methoxyl-styrenes) -1,3,5- triazines of 1,3,5- triazines, 2,4-, 2,4- double (trichloromethyls) -
Double (trichloromethyl) -6- [2- (furans -2- bases) second of 6- [2- (5- methylfuran -2- bases) vinyl] -1,3,5- triazines, 2,4-
Alkenyl] -1,3,5- triazines, double (the trichloromethyl) -6- [2- (4- diethylamino -2- aminomethyl phenyls) vinyl] -1,3 of 2,4-,
Double (trichloromethyl) -6- [2- (3,4- Dimethoxyphenyls) vinyl] -1,3,5- triazines of 5- triazines, 2,4- etc..
As acetophenone based compound, for example, it can include diethoxy acetophenone, 2- hydroxy-2-methyl -1- phenyl third
Alkane -1- ketone, benzil dimethyl ketal, 2- hydroxyls -1- [4- (2- hydroxyl-oxethyls) phenyl] -2- methylpropane -1- ketone, 1- hydroxyls
Butylcyclohexyl phenyl ketone, 2- methyl isophthalic acids-(4- methyl mercaptos phenyl) -2- morpholino propane -1- ketone, 2- benzyl -2- dimethylaminos -
1- (4- morphlinophenyls) butane -1- ketone, 2- hydroxy-2-methyls -1- [4- (1- methyl ethylenes) phenyl] propane -1- ketone it is low
Polymers etc..
As united imidazole, for example, it can include 2,2 '-bis- (2- chlorphenyls) -4,4 ', 5,5 '-tetraphenyl connection miaow
Azoles, 2,2 '-bis- (2,3- dichlorophenyls) -4,4 ', 5,5 '-tetraphenyl bisglyoxaline, 2,2 '-bis- (2- chlorphenyls) -4,4 ', 5,5 ' -
Four (alkoxyl phenyl) bisglyoxalines, 2,2 '-bis- (2- chlorphenyls) -4,4 ', 5,5 '-four (tri-alkoxy phenyl) bisglyoxalines, 4,4 ',
Imidazolium compounds that the phenyl of 5,5 ' positions is replaced by alkoxy carbonyl group etc..In these, 2,2 '-bis- (2- chlorphenyls) -4 is preferably used,
4 ', 5,5 '-tetraphenyl bisglyoxaline, 2,2 '-bis- (2,3- dichlorophenyls) -4,4 ', 5,5 '-tetraphenyl bisglyoxaline.
As long as in addition, not damaging the degree of the effect of the present invention, also can further it include usually used in the field
Other Photoepolymerizationinitiater initiaters etc..As other Photoepolymerizationinitiater initiaters, for example, it can include benzoin based compound, benzophenone
Based compound, thioxanthones based compound, anthracene based compound etc..These can each be used alone or combine two or more
Use.
As benzoin based compound, for example, it can include benzoin, benzoin methyl ether, benzoin ethyl ether, benzene even
Relation by marriage isopropyl ether, benzoin isobutyl ether etc..
As benzophenone based compound, for example, it can include benzophenone, O- benzoyls methyl benzoate, 4- phenyl
Benzophenone, 4- benzoyl -4'- dimethyl diphenyl sulfides, 3,3', 4,4'- tetra- (tert-butyl crosses oxygen carbonyl) benzophenone,
2,4,6- tri-methyl benzophenones, 4,4'- bis- (N, N'- dimethylamino)-benzophenone etc..
As thioxanthones based compound, for example, it can include ITX, 2,4- diethyl thioxanthones, 2,4- bis-
Chloro- 4- propoxythioxanthones of clopenthixal ketone, 1- etc..
As anthracene based compound, for example, 9,10- dimethoxys anthracene, EDMO, 9 can be included,
10- diethoxies anthracene, 2- ethyl -9,10- diethoxy anthracenes etc..
In addition, as other Photoepolymerizationinitiater initiaters, can include TMDPO,
10- butyl -2- chloro-acridines ketone, 2- EAQs, benzil, 9,10- phenanthrenequione, camphorquinone, phenylglyoxalates methyl esters, titanocenes
Compound etc..
In addition, in the present invention, adjuvant is triggered as the photopolymerization that can be applied in combination in Photoepolymerizationinitiater initiater, can
Preferably use more than a kind of the compound in amines, carboxylic acid compound etc..
As photopolymerization trigger adjuvant in amines concrete example, can include triethanolamine, methyl diethanolamine,
The aliphatic amine compounds such as triisopropanolamine, 4- dimethylaminobenzoic acids methyl esters, EDMAB, 4- bis-
Methylaminobenzoate isopentyl ester, 4- dimethylaminobenzoic acid 2- ethylhexyls, benzoic acid 2- dimethylamino ethyl esters, N, N-
The dimethyl-p-toluidine, (common name of 4,4 '-bis- (dimethylamino) benzophenone：Michler's keton), 4,4 '-bis- (diethylaminos) two
The aromatic amines compounds such as Benzophenone.As amines, aromatic amines compound is preferably used.
Carboxylic acid compound, for example, can include phenyl acetic acid, aminomethyl phenyl thioacetic acid, the thio vinegar of ethylphenyl
Acid, Methylethyl phenyl thioacetic acid, 3,5-dimethylphenyl thioacetic acid, methoxyphenylthio acetic acid, Dimethoxyphenyl sulphur
For acetic acid, chlorophenylthio acetic acid, dichlorophenyl thioacetic acid, N-phenylglycine, phenoxyethanoic acid, naphthylthio acetic acid,
The miscellaneous acetate type of the aromatic series such as N- naphthyls glycine, naphthoxy acetic acid.
The content of Photoepolymerizationinitiater initiater in the photosensitive composition of the present invention, relative to coloring phototonus resin
All 100 parts by weight of the solid constituent of composition, preferably comprise 0.1~20 parts by weight, further preferably 1~12 parts by weight.On
In the case of stating the usage amount of Photoepolymerizationinitiater initiater within the above range, make photosensitive polymer combination high sensitivity, pixel portion
Intensity, the flatness on the pixel portion surface it is excellent.
In addition, photopolymerization triggers the usage amount of adjuvant, the solid constituent relative to photosensitive composition is complete
The parts by weight of body 100, preferably comprise 0.1~20 parts by weight, further preferably 1~10 parts by weight.If above-mentioned photopolymerization triggers auxiliary
Within the above range, then the sensitivity efficiency of photosensitive polymer combination is further improved the usage amount of auxiliary agent, uses the combination
The productivity ratio of the colour filter of thing formation can be improved.
Solvent
To the solvent that contains in the photosensitive composition of the present invention, there is no particular restriction, can use in coloring
The various organic solvents used in the field of photosensitive polymer combination.
Above-mentioned solvent, specifically, can include ethylene glycol single methyl ether, ethylene glycol monomethyl ether, ethylene glycol list propyl group
The ethylene glycol monoalkyl ether class such as ether, ethylene glycol monobutyl ether；Diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol (DEG) dipropyl
The diethylene glycol (DEG) dialkyl ether such as base ether, diethylene glycol dibutyl ether；The second such as methylcellosolve acetate, ethyl cellosolve acetate two
Alcohol alkylether acetates class；Propylene glycol monomethyl ether, propylene glycol monoethyl acetic acid esters, propylene glycol monopropyl ether acetic acid
The aklylene glycol alkylether acetates class such as ester；The alkoxy alkyl acetates such as methoxy butyl acetate, acetic acid methoxyl group pentyl ester
Class；Benzene,toluene,xylene, mesitylene etc. are aromatic hydrocarbon；Methyl ethyl ketone, acetone, methyl amyl ketone, methyl-isobutyl
The ketones such as ketone, cyclohexanone；The alcohols such as ethanol, propyl alcohol, butanol, hexanol, cyclohexanol, ethylene glycol, glycerine；3- ethoxy-propionic acid second
The esters such as ester, 3- methoxy methyl propionates；Ring-type esters such as gamma-butyrolacton etc..
Above-mentioned solvent, in terms of coating and drying property, can preferably include above-mentioned solvent mid-boiling point for 100 DEG C
~200 DEG C of organic solvent, it is highly preferred that aklylene glycol alkylether acetates class, ketone, 3- ethoxy-propionic acids can be included
The esters such as ethyl ester, 3- methoxy methyl propionates, it is further preferred that propylene glycol monomethyl ether, propane diols can be included
Single monoethyl ether acetate, cyclohexanone, 3- ethoxyl ethyl propionates, 3- methoxy methyl propionates etc..These solvents can be each single
Solely use or be used in mixed way two or more.
The content of solvent in the photosensitive composition of the present invention, relative to the photoresist group containing it
Compound 100 parts by weight of entirety, preferably comprise 60~90 parts by weight, further preferably 68~85 parts by weight.The content of above-mentioned solvent
In the case of within the above range, using roll coater, spin coater, slit and spin coater, slit coater (sometimes referred to as
For molding coating machine), the coating of the apparatus for coating such as ink-jet when, coating can become good.
Photosensitive composition of the present invention, in addition also can be further containing other macromolecules
Compound, curing agent, surfactant, closely sealed accelerator, antioxidant, ultra-violet absorber, the such addition of anti-flocculating agent
Agent, above-mentioned additive can by those skilled in the art, suitably addition be used in the range of the effect of the present invention is not damaged.
＜ colour filters ＞
The another way of the present invention is directed to use with the colour filter of above-mentioned photosensitive composition manufacture.
The patterned layer that above-mentioned colour filter is formed comprising substrate and on the top of aforesaid substrate.
Aforesaid substrate is sometimes the above-mentioned colour filter substrate of itself, or be also sometimes the colour filter institute in display device etc.
The position being located at, there is no particular restriction.Aforesaid substrate is sometimes glass, silicon (Si), Si oxide (SiOx) or polymeric substrate,
Above-mentioned polymeric substrate is polyether sulfone (polyethersulfone, PES) or makrolon (polycarbonate, PC) sometimes
Deng.
Above-mentioned patterned layer, can be to be coated with above-mentioned color sensation to include the layer of the photosensitive composition of the present invention
Photosensitive resin composition, with layer formed by defined pattern exposure, development and heat cure.Above-mentioned patterned layer can be by carrying out
Method generally known to those skilled in the art and formed.
Colour filter comprising above-mentioned such substrate and patterned layer can be further contained in formed between each pattern every
Wall, can further include black matrix, but be not limited to this.
In addition, the diaphragm that the patterned layer top that can be also further contained in above-mentioned colour filter is formd.
＜ image display devices ＞
In addition, the another way of the present invention is related to the image display device for including above-mentioned colour filter.
The colour filter of the present invention is applicable not only to common liquid crystal display device, is equally applicable to electroluminance display dress
Put, the various image display devices such as plasm display device, field-emission display device.
The light efficiency of the image display device of the present invention is excellent, and exhibit high brilliance, color reproduction is excellent, can show high right
Degree of ratio.
Below in order to specifically describe the present invention, enumerate embodiment and explain.But, the implementation that this specification is related to
Example can be deformed into various other forms, and the scope of this specification should not be construed as limited to the implementation of following detailed descriptions
Example.The embodiment of this specification is provided in order to which those skilled in the art are more completely illustrated with the present invention.Separately
Outside, " % " and " part " of following presentation content, is then weight basis as long as no special instructions.
Synthesis example 1：Triaizine compounds 1
The chloro- 4,6- diaminostilbenes of 2-, the parts by weight of 3,5- triazines 18.4 and 3- (2- ethyl hexyls are added in the parts by weight of water 100
Epoxide) 21 parts by weight of propylamine, reacted at 10 DEG C 1 hour.Obtained reactant is set to have been reacted at 85 DEG C 5 hours.To making
After residue obtained from obtained reactant is leached is washed, an evening is stood in 100 DEG C of thermostat and it is dried,
The compound of following chemical formula 2 is obtained.
[chemical formula 2]
Synthesis example 2：Triaizine compounds 2
The chloro- parts by weight of 4,6- diamino-1,3,5-triazines 18.4 of 2-, the parts by weight of butylamine 21 are added in the parts by weight of water 100,
It is set to react at 10 DEG C 1 hour.Obtained reactant is set to be reacted 5 hours at 85 DEG C.The reactant that makes to obtain is leached and
After obtained residue is washed, a Dinner is stood in 100 DEG C of thermostat, it is dried, obtained following chemical formulas 3
Compound.
[chemical formula 3]
Synthesis example 3：Triaizine compounds 3
The chloro- 4,6- diaminostilbenes of 2-, the parts by weight of 3,5- triazines 18.4,1,3 butylene glycol 21 are added in the parts by weight of water 100
Parts by weight, with the addition of after the parts by weight of sodium hydroxide 10, it is reacted at 10 DEG C 3 hours.Make obtained reactant at 85 DEG C
React 5 hours.After washing residue obtained from being leached to the reactant for making to obtain, a Dinner is stood in 100 DEG C of thermostat,
It is dried, the compound of following chemical formulas 4 has been obtained.
[chemical formula 4]
Resin (B-1)
Prepare the flask with agitator, thermometer, reflux condensing tube, dropping funel and nitrogen ingress pipe, on the other hand, make
For monomer dropping funel, input benzyl maleimide 74.8g (0.20 mole), acrylic acid 43.2g (0.30 mole), vinyl
Toluene 118.0g (0.50 mole), peroxide -2 ethyl hexanoic acid tert-butyl ester 4g, propylene glycol monomethyl ether (PGMEA) 40g
Afterwards, stirring is mixed and prepared, and as chain-transferring agent dropping bath, has prepared to be put into n-dodecane mercaptan 6g, PGMEA 24g and stir
The product of mixing.Then, PGMEA 395g are imported in flask, the atmosphere in flask are replaced into after nitrogen from air, while stirring
Mix side and the temperature of flask is warming up to 90 DEG C.Next, instilling monomer and chain-transferring agent since dropping funel.Maintaining 90 DEG C
While carry out dropping liquid respectively 2 hours, 1 hour after be warming up to 110 DEG C, maintain after 3 hours, import gas introduction tube, start
The bubbling of oxygen/nitrogen=5/95 (v/v) mixed gas.Next, by GMA 28.4g [(0.10 mole),
(being 33 moles of % relative to the carboxyl of the acrylic acid used in this reaction)], 2,2'- di-2-ethylhexylphosphine oxides (4- methyl-6-terts-butyl
Phenol) in 0.4g, triethylamine 0.8g input flask, sustained response 8 hours at 110 DEG C, the acid number for having obtained solid constituent is
70mgKOH/g resin B -1.The weight average molecular weight that the polystyrene for using GPC to determine converts is 16000, molecular weight distribution
(Mw/Mn) it is 2.3.
Resin (B-2)
Propane diols list is imported in the flask for possessing agitator, thermometer, backflow cooling tube, dropping funel and nitrogen ingress pipe
Methylether acetate 182g, the atmosphere in flask is replaced into after nitrogen from air, is warming up to after 100 DEG C, will include methyl
Benzyl acrylate 70.5g (0.40 mole), methacrylic acid 45.0g (0.50 mole), methacrylic acid 2- (2- methyl) Buddha's warrior attendant
Azodiisobutyronitrile 3.6g is with the addition of in alkyl ester 22.0g (0.10 mole) and propylene glycol monomethyl ether 136g mixture
Solution from dropping funel last 2 hours instill flask in, continued at 100 DEG C stirring 5 hours.Next, making burning
Bottle in atmosphere be changed into air from nitrogen, by GMA 30g [0.2 mole, (used relative in this reaction
Methacrylic acid carboxyl, be 40 moles of %)], three (dimethylaminomethyl) phenol 0.9g and quinhydrones 0.145g input burn
In bottle, continue to react 6 hours at 110 DEG C, the acid number for having obtained solid constituent is 99mgKOH/g resin B -2.Using GPC
The weight average molecular weight of the polystyrene conversion of measure is 23000, and molecular weight distribution (Mw/Mn) is 2.3.
The measure of weight average molecular weight (Mw) and number-average molecular weight (Mn) for above-mentioned resin, using GPC method following
Under conditions of carry out.
Device：HLC-8120GPC (eastern Cao's (strain) manufacture)
Post：TSK-GELG4000HXL+TSK-GELG2000HXL (is connected in series)
Column temperature：40℃
Mobile phase solvent：Tetrahydrofuran
Flow velocity：1.0ml/ point
Injection rate：50μl
Detector：RI
Determine sample solution concentration：0.6 mass % (solvent=tetrahydrofuran)
Correction standard substance：TSK STANDARD POLYSTYRENE F-40, F-4, F-1, A-2500, A-500 (east
Cao's (strain) manufactures)
It regard the ratio between weight average molecular weight obtained above and number-average molecular weight as molecular weight distribution (Mw/Mn).
The preparation of colorant dispersion 1
The parts by weight of compound 20.48 of the chemical formula 2 of the synthesis example 1 of pyrrolotriazine derivatives, C.I. pigment blue 15s will be used as：6
9.12 parts by weight, the parts by weight of C.I. acid reds 52 2.88, dispersant containing acrylic [Disperbyk (registration mark) 2000；ビッ
Network ケ ミ ー companies manufacture] 3.84 parts by weight, the parts by weight of resin B -1 2.88, the weight of solvent propylene glycol monomethyl ether acetate 55.04
Measure the parts by weight of the zirconium oxide bead 360 input capacity 140ml's of part, the parts by weight of propylene glycol monomethyl ether 5.76 and 0.2mm diameters
In mayonnaise bottle, kneaded 10 hours at 60 DEG C with coating conditioner, carried out decentralized processing.Then, zirconium oxide bead is removed
Go, obtained dispersion liquid.By membrane filter of the above-mentioned dispersion liquid with 1.0 μm of aperture (pore size), colouring agent point has been obtained
Dispersion liquid 1.
The preparation of colorant dispersion 2
In addition to having used the compound of chemical formula 3 of synthesis example 2 as pyrrolotriazine derivatives, with colorant dispersion 1
Preparation similarly carry out.
The preparation of colorant dispersion 3
In addition to having used the compound of chemical formula 4 of synthesis example 3 as pyrrolotriazine derivatives, with colorant dispersion 1
Preparation similarly carry out.
The preparation of colorant dispersion 4
In addition to no use pyrrolotriazine derivatives, carried out in the same manner as the preparation with colorant dispersion 1.
The preparation of colorant dispersion 5
In addition to having used rhodamine B as rhodamine based dye, enter in the same manner as the preparation with colorant dispersion 1
OK.
The manufacture of photosensitive composition
According to the composition described in table 1 below, the photosensitive composition according to embodiment and comparative example has been manufactured.
【Table 1】
The Production Example of colour filter (glass substrate)
Colour filter has been manufactured using the photosensitive composition manufactured by embodiment and comparative example.That is, will be above-mentioned
After each photosensitive composition is coated with the glass substrate using spin-coating method, it is placed into heating plate, at 100 DEG C
At a temperature of maintain 3 minutes, form film.Next, placing to have on the above-mentioned films makes model of the transmissivity 1~100%
The pattern of interior stepped change and the experiment photomask of 1 μm~50 μm of line/space pattern are enclosed, makes the interval with experiment photomask
For 100 μm, ultraviolet irradiation has been carried out.Now, for ultraviolet light source, the high pressure containing the overall 1kW of g, h, i line is used
Mercury lamp, with 100mJ/Cm2Illumination irradiation, not using special optical filter.Above-mentioned ultraviolet irradiation will be carried out
Film impregnates 2 minutes and developed in pH 10.5 KOH aqueous development solution.The glass of the film will be imposed using distilled water
After glass plate cleaning, nitrogen is sprayed, is dried, heated 1 hour with 220 DEG C of heated ovens, manufactured colour filter.Above-mentioned manufacture
Colour filter thickness be 2.0 μm.
The measure of contrast
Device, which is determined, using contrast determines the pane of tinted glass after the rear baking of embodiment 1~3 and comparative example 1,2
The contrast of (colour filter).
Contrast determines device by color luminance meter (trade name：LS-100, U ニ カ ミ ノ Le タ セ Application シ Application グ (strain)
Manufacture), lamp (trade name：HF-SL-100WLCG, ジ ョ Application ト Application industries (strain) are manufactured) and polarizer (trade name：POLAX-38S、
(strain) Le ケ オ are manufactured) constitute.
Polarizer (POLAX-38S) is provided with backlight so that the interval of polarizer and pane of tinted glass turns into 1mm.
At an upper portion thereof there is provided rotatable polarizer.After confirming that the brightness of backlight is substantially stabilized, it will be set on top
Rotatable polarizer regulation to cross Nicols position, determine pane of tinted glass brightness, next make its rotate 90
Degree, the brightness of pane of tinted glass in parallel position finding.Ratio between two (%) is obtained to spend as a comparison.
Show the result in table 2 below, the contrast value of embodiment 1~3 is expressed as using the coloring phototonus of comparative example 1
The contrast for the pane of tinted glass that resin combination is obtained is used as relative value when standard (100).
The measure of brightness (Y)
The brightness (Y) as described below for determining the pane of tinted glass according to embodiment 1~3 and comparative example 1,2.Glass will be coloured
Glass plate is arranged at spectral photometric colour measuring meter (trade name：CM-3700d, U ニ カ ミ ノ Le タ セ Application シ Application グ (strain) are manufactured), determine C
2 degree of (゜ of light source) under X, Y, the transmission colourity under Z coordinate axle.Brightness (Y) is used as using Y value now.Show the result in following table
In 2.
The brightness value of embodiment 1~3 is expressed as obtaining the photosensitive composition using comparative example 1 in table 2 below
The brightness of the pane of tinted glass arrived is used as relative value when standard (100).
The measure of development residue
Confirm the presence or absence of remnant of pane of tinted glass of embodiment 1~3 and comparative example 1,2 with light microscope.Will
The results are shown in table 2 below, for the result of development residue, zero is expressed as when without remnant, is represented in the presence of remnant
For ×.
The measure of heat resistance
It is (small to 230 DEG C/2hr of the pane of tinted glass (colour filter) after the rear baking of embodiment 1~3 and comparative example 1,2
When) before and after color change compare evaluation.Pane of tinted glass is arranged at spectral photometric colour measuring meter (trade name：CM-3700d、コ
ニ カ ミ ノ Le タ セ Application シ Application グ (strain) manufacture), determine 2 degree of (゜ of illuminant-C) under L*, a*, b* value.Be defined as L*,
The color change of a*, b* use 3-dimensional colorimeter according to【Mathematical expression 1】Calculate, color change value is smaller, can more manufacture highly reliable
The colour filter of property.
【Mathematical expression 1】
△ Eab*=[(△ L*)2+ (△ a*)2+ (△ b*)2]1/2
In table 2 below, the brightness value of embodiment 1~3 is expressed as obtaining the photosensitive composition using comparative example 1
The heat resistance of the pane of tinted glass arrived is used as relative value when standard (100).
The measure of solvent resistance
By the pane of tinted glass (colour filter) after the rear baking of embodiment 1~3 and comparative example 1,2 in 1-METHYLPYRROLIDONE
Impregnated 30 minutes in solvent, evaluation is compared to the color change before and after evaluation.Pane of tinted glass is arranged at spectral photometric colour measuring
Count (trade name：CM-3700d, U ニ カ ミ ノ Le タ セ Application シ Application グ (strain) are manufactured) in, determine 2 degree of (゜ of illuminant-C) under
L*, a*, b* value.L*, a*, b* color change of use 3-dimensional colorimeter are defined as according to above-mentioned【Mathematical expression 1】Calculate,
Color change value is smaller, can more manufacture the colour filter of high reliability.
In table 2 below, the brightness value of embodiment 1~3 is represented：Obtained with the photosensitive composition using comparative example 1
The solvent resistance of the pane of tinted glass arrived is used as relative value when standard (100).
【Table 2】
| Brightness | Contrast | Development residue | Heat resistance | Solvent resistance | |
| Embodiment 1 | 1.05 | 3.14 | ○ | 1.05 | 1.08 |
| Embodiment 2 | 1.07 | 3.21 | ○ | 1.03 | 1.02 |
| Embodiment 3 | 1.06 | 3.65 | ○ | 1.07 | 1.01 |
| Comparative example 1 | 1.00 | 1.00 | ○ | 1.00 | 1.00 |
| Comparative example 2 | 1.09 | 10.27 | × | 0.24 | 0.17 |
In the case of the embodiment 1~3 of triazine for having used the structure of chemical formula 1, with no addition pyrrolotriazine derivatives
Comparative example 1 is similar in brightness and development residue, heat resistance, solvent resistance, but obtains high-contrast, if with having used lysotype
The comparative example 2 of red bright based dye is similar in brightness, but obtains good development residue and high heat resistance and solvent resistance.
Claims (7)
1. photosensitive composition, it is included：
Include the rhodamine based dye existed with particle state and the colouring agent of pigment；With
Include the dispersant of triazine based compound.
2. photosensitive composition according to claim 1, wherein, the triazine based compound is included by following
The compound that chemical formula 1 is represented：
[chemical formula 1]
In chemical formula 1,
R be hydrogen atom, the alkyl of carbon number 1~20, the straight-chain of carbon number 1~20 or the alkoxy of branch's chain state or-NR1R2 bases,
R1 and R2 are each independently the alkyl of hydrogen atom or carbon number 1~20,
Now, the alkyl and alkoxy are replaced or not by the alkoxy of the straight-chain or branch's chain state of hydroxyl or carbon number 1~20
Substitution.
3. photosensitive composition according to claim 1, wherein, the rhodamine based dye is included and is selected from
C.I. acid red 52,87,91,92,94,289；C.I. Indian yellow 73；C.I. alkali red 1:1；C.I. alkaline purple 10,11；And C.I.
More than a kind in solvent red 49.
4. photosensitive composition according to claim 1, wherein, relative to all 100 weights of the colouring agent
Measure part, the triazine based compound containing 0.1~60 parts by weight.
5. photosensitive composition according to claim 1, wherein, also comprising selected from alkali soluble resin, light
At least one in polymerizable compound, Photoepolymerizationinitiater initiater and solvent.
6. the filter manufactured using the photosensitive composition according to any one of 1~claim 5 of claim
Color device.
7. image display device, it includes colour filter according to claim 6.
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| KR1020160036568A KR102383698B1 (en) | 2016-03-28 | 2016-03-28 | Colored photosensitive resin composition, color filter and image display device produced using the same |
| KR10-2016-0036568 | 2016-03-28 |
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| JP (1) | JP6654556B2 (en) |
| KR (1) | KR102383698B1 (en) |
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| CN113201017A (en) * | 2021-04-29 | 2021-08-03 | 宁波中苑颜料有限公司 | Organic pigment dispersant based on triazine derivative and preparation method thereof |
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| KR102383698B1 (en) | 2022-04-05 |
| TWI685713B (en) | 2020-02-21 |
| TW201802585A (en) | 2018-01-16 |
| KR20170111323A (en) | 2017-10-12 |
| JP6654556B2 (en) | 2020-02-26 |
| JP2017182044A (en) | 2017-10-05 |
| CN107239004B (en) | 2021-07-13 |
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