CN102141730A - Coloring composition, color filter and display element - Google Patents

Coloring composition, color filter and display element Download PDF

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Publication number
CN102141730A
CN102141730A CN2010105882170A CN201010588217A CN102141730A CN 102141730 A CN102141730 A CN 102141730A CN 2010105882170 A CN2010105882170 A CN 2010105882170A CN 201010588217 A CN201010588217 A CN 201010588217A CN 102141730 A CN102141730 A CN 102141730A
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Prior art keywords
methyl
pigment
coloured composition
acrylate
solvent
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Inventor
和田夏子
成濑真吾
山口紫
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JSR Corp
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JSR Corp
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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
    • G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/201—Filters in the form of arrays
    • 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
    • G02F1/1303—Apparatus specially adapted to the manufacture of LCDs
    • 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
    • G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Nonlinear Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Manufacturing & Machinery (AREA)
  • Engineering & Computer Science (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Optical Filters (AREA)
  • Liquid Crystal (AREA)
  • Materials For Photolithography (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)

Abstract

The invention relates to a coloring composition, a color filter and a display element. The invention provides a coloring composition which can form pixels with excellent flatness and without the generation of coating leaving parts and is applicable to an inkjet mode. The coloring composition is characterized in that the composition comprises (A) a colorant, (B) a crosslinking agent, (C) a binder resin, (D) a compound represented in the following formula (1), and (E) a solvent. In the formula (1), R21 and R22 represent groups with fluoroalkyl independently of each other; R23 and R24 represent methyl or ethyl independently of each other; X represents a divalent linking group free from fluorine; and m and n represent integers from 1 to 100 independently of each other.

Description

Coloured composition, color filter and display element
Technical field
The present invention relates to a kind of coloured composition, color filter and display element, in more detail, relate to a kind of coloured composition that is used to form the useful dyed layer of the color filter that in the color liquid crystal display arrangement of transmission-type or reflection-type, colour pick-up tube element, organic EL display element, Electronic Paper etc., uses, have the color filter of the dyed layer that forms by this coloured composition, and the display element that possesses this color filter.
Background technology
In the past, when using colored radiation-sensitive composition to make color filter, known method is: on the substrate or be pre-formed on the substrate of light shield layer of expected pattern and be coated with colored radiation-sensitive composition, after the drying, with desired pattern form dry coating is shone radioactive ray (hereinafter referred to as " exposure "), develop, obtain pixel of all kinds (for example referring to patent documentation 1, patent documentation 2) thus.And the optical polymerism composition that also known utilization contains black material forms the method (for example referring to patent documentation 3) of black matrix.And then the painted compositions of thermosetting resin of also known use also obtains the method (for example referring to patent documentation 4) of pixel of all kinds by ink-jetting style.
For the coloured composition that is used for forming pixel, for the stability of improving printing ink, discharge property etc., the known technology (for example referring to patent documentation 5) that makes resin combination contain specific solvent by ink-jetting style.But, the narrow and small zone that the next door that forms on transparency carrier is divided, if form pixel by ink-jetting style, then because the relation of the compatibility on printing ink and surface, next door etc., the shape of pixel forms along the outer edge of pixel or has the thin part of thickness near it and have the shape of thickness maximum portion at the central side of pixel, perhaps its surface forms concaveconvex shape etc., has the problem that forms the pixel of membrane thickness unevenness easily.And, because the relation of the size of the compatibility of printing ink and transparency carrier or the open area divided with the next door, exist printing ink not to be dispersed throughout to produce in the pixel coating to leave over the problem of part (be also referred to as pin hole sometimes, show money or valuables one carries unintentionally, defective etc.) in vain.
The prior art document
Patent documentation
Patent documentation 1: Japanese kokai publication hei 2-144502 communique
Patent documentation 2: Japanese kokai publication hei 3-53201 communique
Patent documentation 3: Japanese kokai publication hei 6-35188 communique
Patent documentation 4: TOHKEMY 2000-310706 communique
Patent documentation 5: TOHKEMY 2006-299090 communique
Summary of the invention
Problem of the present invention is to provide a kind of coloured composition, and it can form the flatness excellence and not produce the pixel that part is left in coating, and is applicable to ink-jetting style.
The inventor furthers investigate, and found that by using specific surfactant can solve above-mentioned problem, has finished the present invention.
That is, the invention provides a kind of coloured composition, it is characterized in that, it contains the compound (below be sometimes referred to as " surfactant (D) ") of (A) colorant, (B) crosslinking chemical, (C) resin glue, (D) following formula (1) expression and (E) solvent.
Figure BSA00000389892800021
(in the formula (1), R 21And R 22Expression independently of each other has the group of fluoro-alkyl, R 23And R 24Represent methyl or ethyl independently of each other, X represents not fluorine-containing divalent linking group, and m and n represent 1～100 integer independently of each other.)
And, the invention provides color filter that possesses the dyed layer that uses above-mentioned coloured composition and form and the display element that possesses this color filter.Herein, " dyed layer " is meant each color pixel that is used for color filter, black matrix etc.
According to coloured composition of the present invention, can form the flatness excellence and not produce the pixel that part is left in coating by ink-jetting style.
Therefore, coloured composition of the present invention can be used for making the color filter of using with the color liquid crystal display device of electronics industry, the color separation color filter of solid-state imager, organic EL display element color filter, the various color filters of Electronic Paper headed by the color filter admirably.
Embodiment
Below, describe the present invention in detail.
Coloured composition
-(A) colorant-
As (A) of the present invention colorant, just be not particularly limited as long as have coloring, can suitably select color and material according to purposes.Specifically, as colorant, any in pigment, dyestuff and the natural colouring matter all can use, but from color filter being required stable on heating aspect, as colorant of the present invention, preferred organic pigment or inorganic pigment.
As organic pigment, can enumerate for example color index (C.I.; The Society Of Dyersand Colourists society distribution) is categorized as the compound of pigment in, specifically can enumerates pigment with following such color index (C.I.) name.
C.I. pigment Yellow 12, C.I. pigment yellow 13, C.I. pigment Yellow 14, C.I. pigment yellow 17, C.I. pigment yellow 20, C.I. pigment yellow 24, C.I. pigment yellow 31, C.I. pigment yellow 55, C.I. pigment yellow 83, C.I. pigment yellow 93, C.I. pigment yellow 109, C.I. pigment yellow 110, C.I. pigment yellow 13 8, C.I. pigment yellow 13 9, C.I. pigment yellow 150, C.I. pigment yellow 153, C.I. pigment yellow 154, C.I. pigment yellow 155, C.I. pigment yellow 166, C.I. pigment yellow 168, C.I. pigment yellow 180, C.I. pigment yellow 211;
C.I. pigment orange 5, C.I. pigment orange 13, C.I. pigment orange 14, C.I. pigment orange 24, C.I. pigment orange 34, C.I. pigment orange 36, C.I. pigment orange 38, C.I. pigment orange 40, C.I. pigment orange 43, C.I. pigment orange 46, C.I. pigment orange 49, C.I. pigment orange 61, C.I. pigment orange 64, C.I. pigment orange 68, C.I. pigment orange 70, C.I. pigment orange 71, C.I. pigment orange 72, C.I. pigment orange 73, C.I. pigment orange 74;
C.I. paratonere 1, C.I. paratonere 2, C.I. paratonere 5, C.I. paratonere 17, C.I. pigment red 31, C.I. pigment red 32, C.I. pigment red 41, C.I. pigment red 122, C.I. pigment red 123, C.I paratonere 144, C.I. pigment red 149, C.I. paratonere 166, C.I. paratonere 168, C.I. paratonere 170, C.I. paratonere 171, C.I. paratonere 175, C.I. paratonere 176, C.I. paratonere 177, C.I. paratonere 178, C.I. paratonere 179, C.I. paratonere 180, C.I. paratonere 185, C.I. paratonere 187, C.I. paratonere 202, C.I. paratonere 206, C.I. Pigment Red 207, C.I. paratonere 209, C.I. pigment red 21 4, C.I. paratonere 220, C.I. paratonere 221, C.I. paratonere 224, C.I. paratonere 242, C.I. paratonere 243, C.I. paratonere 254, C.I. paratonere 255, C.I. paratonere 262, C.I. paratonere 264, C.I. paratonere 272;
C.I. pigment violet 1, C.I. pigment violet 19, C.I. pigment Violet 23, C.I. pigment violet 29, C.I. pigment violet 32, C.I. pigment violet 36, C.I. pigment violet 38;
C.I. pigment blue 15, C.I. pigment blue 15: 3, C.I. pigment blue 15: 4, C.I. pigment blue 15: 6, C.I. pigment blue 60, C.I. alizarol saphirol 80;
C.I. pigment Green 7, C.I. pigment green 36, C.I. naphthol green 58.
These organic pigments can use separately or mix more than 2 kinds and use.
Among the present invention, organic pigment also can be made with extra care the back by recrystallization method, reprecipitation method, solvent cleaning method, sublimed method, vaccum heating method or their combination and use.And organic pigment preferably uses after with the primary particle miniaturization by so-called salt milling.As the method for salt milling, for example be disclosed in the Japanese kokai publication hei 08-179111 communique.
And, as above-mentioned inorganic pigment, for example can enumerate titanium dioxide, barium sulphate, lime carbonate, zinc paste, lead sulfate, chrome yellow, zinc yellow, colcother (red iron oxide (III)), cadmium red, ultramarine, Prussian blue, chrome oxide green, cobalt green, umber, black, the synthetic iron oxide black of titanium, carbon black etc.
These colorants also can be as required use after with its particle surface modification with resin.Carry out modified resins as particle surface, can enumerate vector resin that TOHKEMY 2001-108817 communique for example put down in writing or commercially available various pigment dispersing resins pigment.As the resin-coated method of carbon blacksurface, the method that can adopt for example Japanese kokai publication hei 9-71733 communique, Japanese kokai publication hei 9-95625 communique, Japanese kokai publication hei 9-124969 communique etc. to be put down in writing.
Above-mentioned colorant can use separately or mix more than 2 kinds and use.
When coloured composition of the present invention is used to form pixel, because to the high meticulous color development of pixel request, so as (A) colorant, the preferred high colorant of color emissivity specifically, preferably uses organic pigment.On the other hand, when coloured composition of the present invention being used to form black matrix,,, preferably use organic pigment or carbon black as (A) colorant because black matrix is required light-proofness.
But, use contains the blue pixel of the coloured composition formation of blue colorant, particularly blue pigment, because of after high temperature heating when curing operation with the xanthochromia of resin glue composition, crosslinking chemical composition or the crystal transition of blue pigment itself etc., the problem of the transparency, color characteristics reduction can appear.
And, use the pixel contain the coloured composition of colorant and to form with azo bond, because of after high temperature heating when curing operation, the problem that this azo bond is decomposed, excitation descends can appear.As colorant with azo bond, can enumerate the monoazo pigment of disclosed pigment representative in for example C.I. pigment yellow 150, the TOHKEMY 2001-354869 communique, the disazo pigment of C.I. paratonere 242 representatives etc., wherein monoazo pigment is easily faded by the high temperature heating.In the monoazo pigment, the molecular compound that the compound of being represented by the compound of following formula (I) expression or its dynamic isomer and following formula (II) forms, the inclusion compound that forms of the object of representing by the main body of the compound of following formula (I) expression or its dynamic isomer and following formula (II) (below be sometimes referred to as " specific yellow uitramarine ") particularly, be the yellow uitramarine of the transparency and excitation excellence, but easily faded by the high temperature heating.
Surprisingly, utilize coloured composition of the present invention can solve above-mentioned stable on heating problem.
(in the formula (II), R a～R cRepresenting hydrogen atom independently of each other or having or do not have carbon number that hydroxyl replaces is 1～4 alkyl.)
Surprisingly, utilize coloured composition of the present invention can solve above-mentioned stable on heating problem.
And, use the green pixel of the zinc halide phthalocyanine color formation of C.I. naphthol green 58 representatives in a single day to be exposed in the organic solvent, the problem of coloring components stripping, excitation decline can appear.Surprisingly, utilize coloured composition of the present invention also can solve the problem of above-mentioned solvent resistance.
Among the present invention, from pixel that forms the transparency and excitation excellence or the aspect that forms the black matrix of light-proofness excellence, coloured composition total solid form divide in (A) colorant contain proportional 5～70 quality % that are preferably, more preferably 5～60 quality %.Herein, Gu formation divides the composition that is meant except solvent described later.
Colorant among the present invention can together use with spreading agent, dispersing aid as required.As above-mentioned spreading agent, can use for example suitable spreading agent such as kation system, negative ion system, nonionic system, but the preferred polymers spreading agent.Specifically, can enumerate acrylic acid series copolymer, polyurethane, polyester, polyethyleneimine, polyallylamine etc.
Such spreading agent can obtain by the commercial channel, for example as acrylic acid series copolymer, can enumerate Disperbyk-2000, Disperbyk-2001, BYK-LPN6919, BYK-LPN21116 (above is that Bi Ke chemistry (BYK) company makes), can enumerate Disperbyk-161 as polyurethane, Disperbyk-162, Disperbyk-165, Disperbyk-167, Disperbyk-170, Disperbyk-182 (above is that Bi Ke chemistry (BYK) company makes), Solsperse76500 (manufacturing of LUBRIZOL (strain) company), Solsperse24000 (manufacturing of LUBRIZOL (strain) company) can be enumerated as polyethyleneimine, AdisperPB821 can be enumerated as polyester, Adisper PB822, Adisper PB823, Adisper PB824, Adisper PB827, Adisper PB880, Adisper PB881 (above is that aginomoto fine chemistry Co., Ltd. makes) etc.
These spreading agents can use separately or mix more than 2 kinds and use.With respect to 100 mass parts (A) colorant, the content of spreading agent be generally 100 mass parts following, be preferably 1～70 mass parts, 10～50 mass parts more preferably.In this case, if the content of spreading agent surpasses 100 mass parts, then the intensity of resulting dyed layer etc. might be impaired.
As above-mentioned dispersing aid, can enumerate for example pigment derivative, specifically can enumerate the sulfonic acid of copper phthalocyanine, diketopyrrolopyrrolecocrystals, quinophthalone etc.
-(B) crosslinking chemical-
(B) crosslinking chemical among the present invention is so long as have the monomer of polymerisable group more than 2 and just be not particularly limited.As polymerisable group, can enumerate for example ethylenic unsaturated group, Oxyranyle, oxetanyl, N-alkoxy methyl amino etc.Among the present invention, as (B) crosslinking chemical, be preferably selected from the compound that (b1) have 2 above N-alkoxy methyl amino (below be sometimes referred to as " crosslinking chemical (b1) ") and (b2) at least a in multifunctional (methyl) acrylate (below be sometimes referred to as " crosslinking chemical (b2) ").When the formation of the dyed layer that coloured composition of the present invention is used to utilize ink-jetting style to carry out, when particularly making heat cured ink jet,, preferably they are share from the thermotolerance of formed dyed layer and the aspect of flatness.And, when giving radiation-sensitive,, preferably use crosslinking chemical (b2) from the aspect of sensitivity to coloured composition of the present invention.
As above-mentioned crosslinking chemical (b1), just be not particularly limited as long as have 2 above N-alkoxy methyl amino, can enumerate for example have the melamine structure, the compound of benzoguanamine structure, urea structure etc.Need to prove that " melamine structure, benzoguanamine structure " is meant that having 1 above triazine ring or phenyl replaces the chemical constitution of triazine ring as basic framework, its notion also comprises melamine, benzoguanamine or their condensation product.The cross-linking reaction of crosslinking chemical (b1) is in the curable that brings the dyed layer excellence, even follow the high temperature heating also to be difficult to take place the characteristic of xanthochromia owing to having, so also bring the thermotolerance of dyed layer excellence.As the concrete example of crosslinking chemical (b1), can enumerate the compound of following formula (b1-1)～(b1-5) expression.
Figure BSA00000389892800081
In the formula (b1-2), R 5～R 6Represent that independently of each other carbon number is 1～4 straight chain shape or the alkyl that props up chain.
In formula (b1-1) and the formula (b1-3)～(b1-5), R 1～R 4And R 7～R 20Represent that independently of each other hydrogen atom or carbon number are 1～4 straight chain shape or the alkyl that props up chain.But the R in the formula (b1-1) 1～R 4Among at least 2, formula (b1-3) in R 7～R 10Among at least 2, formula (b1-4) in R 11～R 16Among at least 2 and formula (b1-5) in R 17～R 20Among at least 2 be that carbon number is the alkyl of a straight chain shape of 1～4 or a chain.
Specifically can enumerate methyl, ethyl, n-pro-pyl, isopropyl, normal-butyl, isobutyl etc.
Among the present invention, as crosslinking chemical (b1), from the thermotolerance of dissolubility solvent and formed dyed layer, the aspect of solvent resistance, the compound that preferably has melamine structure, benzoguanamine structure or these two kinds of structures, more preferably above-mentioned formula (b1-4) or the compound of formula (b1-5) expression or their condensation product.
Among the present invention, crosslinking chemical (b1) can use separately or mix more than 2 kinds and use.
As above-mentioned crosslinking chemical (b2); just be not particularly limited so long as have the compound of (methyl) acryloyl group more than 2, can enumerate for example aliphatic polyhydroxy compound and (methyl) acrylic acid ester; multifunctional (methyl) acrylate through caprolactone modification; multifunctional (methyl) acrylate through the alkylene oxide modification; polyfunctional carbamate (methyl) acrylate that makes (methyl) acrylate with hydroxyl and polyfunctional isocyanate reaction and obtain; multifunctional (methyl) acrylate that makes (methyl) acrylate with hydroxyl and anhydride reaction and obtain etc. with carboxyl.When the formation of the dyed layer that coloured composition of the present invention is used to utilize ink-jetting style to carry out, the crosslinked curing reaction that produces between (methyl) acryloyl group of crosslinking chemical (b2) brings the flatness of dyed layer excellence.
As above-mentioned aliphatic polyhydroxy compound, can enumerate for example ethylene glycol, propylene glycol, polyglycol, 2 yuan such aliphatic polyhydroxy compound of polypropylene glycol herein; Glycerine, trimethylolpropane, pentaerythrite, the aliphatic polyhydroxy compound more than 3 yuan that dipentaerythritol is such, as above-mentioned (methyl) acrylate with hydroxyl, can enumerate for example (methyl) acrylic acid 2-hydroxyl ethyl ester, trimethylolpropane two (methyl) acrylate, pentaerythrite three (methyl) acrylate, dipentaerythritol five (methyl) acrylate, dimethyl allene acid glyceride etc., as above-mentioned polyfunctional isocyanate, can enumerate for example toluene diisocyanate, hexamethylene diisocyanate, MDI, isophorone diisocyanate etc., as above-mentioned acid anhydrides, can enumerate for example succinic anhydride, maleic anhydride, glutaric anhydride, itaconic anhydride, phthalic anhydride, the acid anhydrides of the dibasic acid that hexahydrophthalic anhydride is such, pyromellitic acid dianhydride, bibenzene tetracarboxylic dianhydride, the tetra-atomic acid dianhydride that the benzophenone tetracarboxylic acid dianhydride is such.
And, as above-mentioned multifunctional (methyl) acrylate through caprolactone modification, can enumerate for example compound of the middle record in the paragraph of TOHKEMY 11-44955 communique (0015)～(0018), as above-mentioned multifunctional (methyl) acrylate, can enumerate the oxirane and/or epoxy pronane modification two (methyl) acrylate of bisphenol-A through the alkylene oxide modification, the oxirane of isocyanuric acid and/or epoxy pronane modification two (methyl) acrylate, the oxirane of isocyanuric acid and/or epoxy pronane modification three (methyl) acrylate, the oxirane of trimethylolpropane and/or epoxy pronane modification three (methyl) acrylate, the oxirane of pentaerythrite and/or epoxy pronane modification three (methyl) acrylate, the oxirane of pentaerythrite and/or epoxy pronane modification four (methyl) acrylate, the oxirane of dipentaerythritol and/or epoxy pronane modification five (methyl) acrylate, the oxirane of dipentaerythritol and/or epoxy pronane modification six (methyl) acrylate etc.
Among these crosslinking chemicals (b2); preferred aliphat polyol and (methyl) acrylic acid ester, through multifunctional (methyl) acrylate, polyfunctional carbamate (methyl) acrylate of caprolactone modification or have multifunctional (methyl) acrylate of carboxyl, it has (methyl) acryloyl group more than 3.
Among the present invention, crosslinking chemical (b2) can use separately or mix more than 2 kinds and use.
When share crosslinking chemical (b1) and crosslinking chemical (b2), as crosslinking chemical (b2), from the solvent resistance and the stable on heating aspect of formed dyed layer, be preferably selected from multifunctional (methyl) acrylate that 3 officials with hydroxyl can be above and have in can above multifunctional (methyl) acrylate at least a kind of 3 officials of carboxyl.Think that the reaction zone of N-alkoxy methyl amino of the hydroxyl of crosslinking chemical (b2) and/or carboxyl and crosslinking chemical (b1) gives the solvent resistance of dyed layer excellence.
Can above multifunctional (methyl) acrylate, especially preferably pentaerythrite three (methyl) acrylate, dipentaerythritol five (methyl) acrylate as 3 officials with hydroxyl.And the acid value with multifunctional (methyl) acrylate that 3 officials of carboxyl can be above is preferably 30～300mgKOH/g, more preferably 50～250mgKOH/g.The reaction product of reaction product, dipentaerythritol five (methyl) acrylate and the succinic anhydride of preferred especially pentaerythrite three (methyl) acrylate and succinic anhydride.
Among the present invention, multifunctional (methyl) acrylate with hydroxyl can use separately or mix respectively more than 2 kinds with multifunctional (methyl) acrylate with carboxyl and use.Certainly, also multifunctional (methyl) acrylate with hydroxyl independent or more than 2 kinds can be mixed use with multifunctional (methyl) acrylate with carboxyl independent or more than 2 kinds.
With respect to 100 mass parts (A) colorant, the total content of (B) crosslinking chemical among the present invention is preferably 5～1,000 mass parts, 20～300 mass parts more preferably.At this moment, if the content of crosslinking chemical is very few, then have the intensity of dyed layer and the tendency of surface smoothing decline, if the content of crosslinking chemical is too much on the other hand, then pigment concentration reduces relatively, therefore may be difficult to reach aim colour concentration as film.
When share crosslinking chemical (b1) and crosslinking chemical (b2), their blending ratio is preferably 90: 10～10: 90 by quality ratio, more preferably 80: 20～20: 80.And, at this moment, be selected from multifunctional (methyl) acrylate among the crosslinking chemical (b2) and have at least a in multifunctional (methyl) acrylate of carboxyl and contain proportional above, 10～80 quality % more preferably of 5 quality % that are preferably with hydroxyl.By using each crosslinking chemical in this way, the thermotolerance of dyed layer, solvent resistance, flatness excellence.
-(C) resin glue-
(C) resin glue as among the present invention is not particularly limited, but be preferably have carboxyl, the resin of acidic functionality such as phenolic hydroxyl group.Wherein, the polymkeric substance (hereinafter referred to as " carboxylic polymkeric substance ") that preferably has carboxyl, especially preferably have 1 above carboxyl ethylenically unsaturated monomers (hereinafter referred to as " unsaturated monomer (c1) ") but with the multipolymer of the ethylene unsaturated monomer (hereinafter referred to as " unsaturated monomer (c2) ") of other copolymerization.
As above-mentioned unsaturated monomer (c1), for example can enumerate (methyl) acrylic acid, maleic acid, maleic anhydride, mono succinate [2-(methyl) acryloxy ethyl) ester, ω-carboxyl polycaprolactone list (methyl) acrylate etc.These unsaturated monomers (c1) can use separately or mix more than 2 kinds and use.
In the multipolymer of unsaturated monomer (c1) and unsaturated monomer (c2), the copolymerization ratio of unsaturated monomer (c1) is preferably 5～50 quality %, 10～40 quality % more preferably.By make unsaturated monomer (c1) copolymerization with such scope, can access the coloured composition of storage stability, alkali development excellence.
And,, can enumerate for example N-phenylmaleimide, the such N-position substituted maleimide amine of N-cyclohexyl maleimide as above-mentioned unsaturated monomer (c2);
Styrene, α-Jia Jibenyixi, to the such aromatic ethenyl compound of hydroxyl-α-Jia Jibenyixi;
(methyl) methyl acrylate, (methyl) n-butyl acrylate, (methyl) acrylic acid-2-ethyl caproite, (methyl) acrylic acid 2-hydroxyl ethyl ester, (methyl) allyl acrylate, (methyl) benzyl acrylate, polyglycol (n=2～10) methyl ethers (methyl) acrylate, polypropylene glycol (n=2～10) methyl ethers (methyl) acrylate, single (methyl) acrylate of polyglycol (n=2～10), single (methyl) acrylate of polypropylene glycol (n=2～10), (methyl) cyclohexyl acrylate, (methyl) isobornyl acrylate, three ring [5.2.1.0 2,6] decane-8-base (methyl) acrylate, dihydro bicyclic pentadiene (dicyclopentenyl) (methyl) acrylate, list (methyl) acrylic acid glyceride, (methyl) acrylic acid 4-hydroxylphenyl ester, to the such esters of unsaturated carboxylic acids of oxirane modification (methyl) acrylate of cumyl phenol;
What polystyrene, poly-(methyl) methyl acrylate, poly-(methyl) n-butyl acrylate, polysiloxane were such has the macromonomer etc. of list (methyl) acryloyl group at the polymer molecule chain end.
These unsaturated monomers (c2) can use separately or mix more than 2 kinds and use.
As the concrete example of unsaturated monomer (c1), can enumerate for example disclosed multipolymer in Japanese kokai publication hei 7-140654 communique, Japanese kokai publication hei 8-259876 communique, Japanese kokai publication hei 10-31308 communique, Japanese kokai publication hei 10-300922 communique, Japanese kokai publication hei 11-174224 communique, Japanese kokai publication hei 11-258415 communique, TOHKEMY 2000-56118 communique, TOHKEMY 2004-101728 etc. with the multipolymer of unsaturated monomer (c2).
And; among the present invention; also can be as disclosed in for example Japanese kokai publication hei 5-19467 communique, Japanese kokai publication hei 6-230212 communique, Japanese kokai publication hei 7-207211 communique, Japanese kokai publication hei 11-140144 communique, the TOHKEMY 2008-181095 communique etc., use the carbonyl bearing polymer that has polymerism unsaturated links such as (methyl) acryloyl group at side chain as resin glue.
(GPC, eluting solvent: tetrahydrofuran) weight-average molecular weight of the polystyrene conversion of Ce Dinging (below be sometimes referred to as " Mw ") is generally 1,000～300,000, is preferably 3,000-100,000 gel permeation chromatography that passes through of the resin glue among the present invention.If Mw is too small, then have the reductions such as residual film ratio of gained tunicle, or pattern form, thermotolerance etc. are impaired, or the possibility of electric properties deteriorate, on the other hand,, then exist pattern form impaired if Mw is excessive, or the possibility of printing ink discharge property variation.
And, the Mw of the resin glue among the present invention is with (GPC, eluting solvent: tetrahydrofuran) ratio (Mw/Mn) of the number-average molecular weight of the polystyrene conversion of Ce Dinging (below be sometimes referred to as " Mn ") is preferably 1.0～5.0, more preferably 1.0～3.0 by gel permeation chromatography.
Resin glue among the present invention can be by the known method manufacturing, can also control its structure, Mw, Mw/Mn by TOHKEMY 2003-222717 communique for example, TOHKEMY 2006-259680 communique, the international middle disclosed method such as No. 07/029871 pamphlet that disclose.
Among the present invention, resin glue can use separately or mix more than 2 kinds and use.
Among the present invention, with respect to 100 mass parts (A) colorant, the content of resin glue is generally 10～1,000 mass parts, is preferably 20～500 mass parts.At this moment, if the content of resin glue is very few, for example then there are the storage stability of resulting coloured composition or the possibility that alkali development descends, on the other hand, if the content of resin glue is too much, then colorant concentration descends relatively, therefore may be difficult to reach aim colour concentration as film.
-surfactant (D)-
Coloured composition of the present invention contains surfactant (D), is the compound of above-mentioned formula (1) expression.Because surfactant (D) has hydroxyl, so coloured composition strengthens the compatibility of glass substrate, coating ductility is good, therefore can be formed on by ink-jetting style and not produce the pixel that part is left in coating in the next door.And, think that the curing reaction due to the heat cross-linking of the N-alkoxy methyl amino of the hydroxyl of surfactant (D) and above-mentioned crosslinking chemical (b1) further improves the solvent resistance and the thermotolerance of dyed layer.
In the above-mentioned formula (1),, for example can enumerate and to replace or the divalent alkyl of non-replacement, a plurality of divalent alkyl connect the divalent group that obtains etc. by containing heteroatomic at least 1 linking group as the divalent linking group that X represents.As the concrete example of this divalent alkyl, can enumerate alkylidene, cycloalkylidene, olefin 2 base, cyclenes two bases, arlydene etc.Need to prove that this alkylidene can be the straight chain shape, also can be a chain.And, as the above-mentioned concrete example that contains heteroatomic linking group, can enumerate-O-,-S-,-CO-,-SO 2-,-COO-,-SO 3-,-CONH-,-OCONH-,-SO 2NH-etc.At X is a plurality of alkyl when containing heteroatomic at least 1 linking group and connect the divalent group that obtains, a plurality of alkyl can be identical or different, and, when to contain heteroatomic linking group be a plurality of, a plurality of contain heteroatomic linking group also can be identical or different.
Among the present invention, from improving the aspect of desired effect, the total carbon atom number that X had is preferably 1～50, and more preferably 1～20.If the total carbon atom number that X had is too much, the coating ductility of the then hydroxyl value step-down of surfactant (D), so coloured composition on substrate might variation.X is the divalent alkyl of carbon number 1～20 more preferably, is preferably the divalent alkyl of carbon number 1～10 especially.
And, in the above-mentioned formula (1), as R 21And R 22,, preferably have carbon number and be the group of 1～4 perfluoroalkyl, preferred especially CF from improving the aspect of desired effect 3CH 2-, CF 3CH 2CH 2-, CF 3CF 2CH 2-, CF 3CF 2CH 2CH 2-, CF 3CF 2CF 2CH 2-, CF 3CF 2CF 2CH 2CH 2-, CF 3CF 2CF 2CF 2CH 2-, CF 3CF 2CF 2CF 2CH 2CH 2-.
And in the above-mentioned formula (1), m+n is preferably 2～40, more preferably 3～30.At this moment, if m+n is too small, then the flatness of pixel might variation, on the other hand, if m+n is excessive, the hydroxyl value step-down of surfactant (D) then, therefore there be the coating ductility variation of coloured composition on substrate, or the possibility that reduces with the compatibility of other compositions.
As the concrete example of surfactant (D), can enumerate the compound that following formula is represented.
Figure BSA00000389892800141
(in the formula, R 21～R 24, the R in m and n and the above-mentioned formula (1) 21～R 24, m and n implication identical, R represents ethylidene or methyl ethylidene, l represents 1～40 integer.)
Surfactant (D) can obtain by the commercial channel, for example can enumerate the commercially available PF-7002 of OMNOVA company (R in the above-mentioned formula (1-1) 21And R 22Be CF 3CF 2CF 2CF 2CH 2CH 2-, R 23And R 24Surfactant for methyl, m+n=4～5), PF-151N (R in the above-mentioned formula (1-2) 21And R 22Be CF 3CF 2CH 2-, R 23And R 24For methyl, R are that the mean value of ethylidene, m and n all is 4, the mean value of l is 21 surfactant) etc.
Among the present invention, surfactant (D) can use separately or mix more than 2 kinds and use.
With respect to the solid formation branch of 100 mass parts except that the aftermentioned solvent, the content of surfactant (D) is generally 0.01～2.0 mass parts, is preferably 0.02～1.5 mass parts, 0.05～1.0 mass parts more preferably.If the content of surfactant (D) is very few, then may not obtain desired effect, on the other hand, if the content of surfactant (D) is too much, then the dyed layer surface might become coarse.
Among the present invention, as surfactant, also can use surfactant (D) known fluorine in addition with surfactant (D) is surfactant, silicon-type surfactant etc.
-(E) solvent-
Coloured composition of the present invention cooperates solvent usually and is prepared into fluid composition.As solvent, so long as will constitute (A)～(D) composition of coloured composition and additive component described later disperses or dissolves and not with the reaction of these compositions, have appropriate volatile solvent, just can suitably select to use.
When the formation of the dyed layer that coloured composition of the present invention is used to utilize ink-jetting style to carry out, all preferably contain in the solvents boiling point under 70 quality %, 1 atmospheric pressure above, more preferably 80～100 quality %, preferred especially 90～100 quality % be preferably solvent (following also be sometimes referred to as " high boiling solvent ") more than 180 ℃, more preferably 200 ℃～290 ℃ solvent, be preferably 220 ℃～solvent below 280 ℃ especially.If containing of high boiling solvent is proportional very few, then coloured composition is dry easily, so printing ink discharge property variation, moreover, the levelling speed of coloured composition and the balance of rate of drying are destroyed, so also variation of the flatness of pixel and the coating ductility of coloured composition on substrate.
As above-mentioned high boiling solvent, can enumerate for example propylene-glycol diacetate, 1,3 butylene glycol diacetate esters, 1,6-hexanediol diacetate esters etc. are the solvent with 2 acetic acid esters structures of representative with the dibasic alcohol diacetate esters;
Diethylene glycol monomethyl ether acetic acid esters, diethylene glycol monoethyl ether acetic acid esters, diglycol monotertiary positive propyl ether acetic acid esters, diethylene glycol monoethyl ether acetic acid esters, diglycol monotertiary n-butyl ether acetic acid esters, dipropylene glycol monomethyl ether acetic acid esters, ethylene glycol monomethyl ether acetate, ethyleneglycol monophenylether acetic acid esters, propylene glycol butyl ether acetic acid esters, acetate 3-methyl-3-methoxyl butyl ester etc. have the solvent of 1 acetic acid esters structure;
The glycol monomethyl isoamyl oxide, ethylene glycol ether, ethyleneglycol monophenylether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, the diglycol monotertiary positive propyl ether, the diglycol monotertiary n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol list ether, dipropylene glycol monomethyl ether, the single ether of dipropylene glycol, the single positive propyl ether of dipropylene glycol, the dipropylene glycol mono-n-butyl ether, the tripropylene glycol monomethyl ether, tripropylene glycol list ether, benzylisoeugenol, hexyl ether, diethyl carbitol, acetonyl acetone, isophorone, caproic acid, sad, the 1-octanol, 1 nonyl alcohol, benzyl acetate, ethyl benzoate, diethy-aceto oxalate, diethyl maleate, gamma-butyrolacton, ethylene carbonate, propylene carbonate, N-Methyl pyrrolidone etc.
Wherein, from the aspect of the dispersion stabilization of coloured composition, the solvent that preferably has 2 acetic acid esters structures, more preferably dibasic alcohol diacetate esters, further preferred carbon number is the diacetate esters of 2～6 dibasic alcohol, preferred especially 1,3 butylene glycol diacetate esters.
Above-mentioned high boiling solvent can use separately or mix more than 2 kinds and use.
And, when the formation of the dyed layer that coloured composition of the present invention is used to utilize ink-jetting style to carry out, also can use 1 boiling point under the atmospheric pressure less than 180 ℃ solvent with high boiling solvent.
As the solvent of the boiling point under 1 atmospheric pressure, for example can enumerate less than 180 ℃:
Methyl alcohol, ethanol, the such alcohols of phenmethylol;
Glycol monoethyl ether, ethylene glycol monoethyl ether, ethylene glycol propyl ether, ethylene glycol mono-n-butyl ether, propylene glycol monomethyl ether, such (gathering) the alkylene glycol monoalky lether of dihydroxypropane single-ether;
Ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol propyl ether acetic acid esters, propylene glycol methyl ether acetate, propylene glycol monoethyl ether acetate, such (gathering) the alkylene glycol monoalky lether acetic acid esters of acetate 3-methoxyl butyl ester;
The ethers of other that diethylene glycol dimethyl ether, diglycol methyl ethyl ether, tetrahydrofuran are such;
Ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone, diacetone alcohol (4-hydroxy-4-methyl pentane-2-ketone), 4-hydroxy-4-methyl hexane-2-one;
Methyl lactate, the such lactic acid alkyl ester of ethyl lactate;
Ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, the formic acid n-pentyl ester, isoamyl acetate, n-butyl propionate, ethyl butyrate, the butyric acid n-propyl, isopropyl isobutyrate, the positive butyl ester of butyric acid, hydroxyl ethyl acetate, ethoxy ethyl acetate, 3-methoxypropionic acid methyl esters, 3-methoxy propyl acetoacetic ester, 3-ethoxy-propionic acid methyl esters, the 3-ethoxyl ethyl propionate, methyl pyruvate, ethyl pyruvate, the pyruvic acid n-propyl, methyl acetoacetate, ethyl acetoacetate, 2-hydroxy-2-methyl ethyl propionate, 2-hydroxy-3-methyl methyl butyrate, such ester classes such as 2-ketobutyric acid ethyl ester;
Toluene, the such aromatic hydrocarbon of dimethylbenzene;
N, amide-type that dinethylformamide, N,N-dimethylacetamide are such etc.
Among these other solvents, from dissolubility, set out in aspects such as pigment-dispersing, preferred phenmethylol, ethylene glycol mono-n-butyl ether, propylene glycol monomethyl ether, dihydroxypropane single-ether, ethylene glycol monomethyl ether acetate, propylene glycol methyl ether acetate, propylene glycol monoethyl ether acetate, acetate 3-methoxyl butyl ester, diethylene glycol dimethyl ether, the diglycol ethyl methyl ether, cyclohexanone, the 2-heptanone, the 3-heptanone, n-butyl acetate, isobutyl acetate, the formic acid n-pentyl ester, isoamyl acetate, acetate 3-methoxyl butyl ester, n-butyl propionate, ethyl butyrate, isopropyl isobutyrate, the positive butyl ester of butyric acid, 3-methoxy propyl acetoacetic ester, 3-ethoxy-propionic acid methyl esters, the 3-ethoxyl ethyl propionate, ethyl pyruvate.
Boiling point under above-mentioned 1 atmospheric pressure can use or mix use more than 2 kinds separately less than 180 ℃ solvent.
On the other hand, coloured composition of the present invention is being used for rotary coating or slit die when coating, all preferably contain more than the 70 quality % in the solvents, more preferably the boiling point under 1 atmospheric pressure of 80～100 quality %, preferred especially 90～100 quality % preferably less than 180 ℃ solvent, more preferably 100 ℃～180 ℃ solvent, be preferably 120 ℃～solvent below 180 ℃ especially.
When coloured composition of the present invention being used for the coating of rotary coating or slit die, as the solvent of the boiling point under 1 atmospheric pressure less than 180 ℃, from the coating aspect, preferably above-mentioned (gathering) alkylene glycol monoalky lether, (gathering) alkylene glycol monoalky lether acetic acid esters, ethers, ketone, the ester class, preferred especially ethylene glycol mono-n-butyl ether, propylene glycol monomethyl ether, dihydroxypropane single-ether, ethylene glycol monomethyl ether acetate, propylene glycol methyl ether acetate, propylene glycol monoethyl ether acetate, acetate 3-methoxyl butyl ester, diethylene glycol dimethyl ether, the diglycol ethyl methyl ether, cyclohexanone, n-butyl acetate, isobutyl acetate, isoamyl acetate, acetate 3-methoxyl butyl ester, n-butyl propionate, 3-methoxy propyl acetoacetic ester, 3-ethoxy-propionic acid methyl esters, the 3-ethoxyl ethyl propionate.
These solvents can use separately or mix more than 2 kinds and use.
Discharge aspects such as property, coating, storage stability from the printing ink of resulting coloured composition, the content of solvent is preferably the amount that the total concentration that makes each composition beyond desolventizing becomes 5～35 quality %, more preferably makes described total concentration become the amount of 10～30 quality %.
-Photoepolymerizationinitiater initiater-
By making coloured composition of the present invention contain Photoepolymerizationinitiater initiater, can give radiation-sensitive.Photoepolymerizationinitiater initiater among the present invention is the compound that can produce the spike of the cross-linking reaction that can cause above-mentioned (B) crosslinking chemical by the exposure of luminous ray, ultraviolet ray, far ultraviolet, electron ray, X ray isoradial.
As such Photoepolymerizationinitiater initiater, for example can enumerate thioxanthones based compound, acetophenone based compound, bisglyoxaline based compound, triazine based compound, O-acyl group oxime compound,
Figure BSA00000389892800181
Salt based compound, benzoin based compound, benzophenone based compound, α-diketone based compound, encircle quinone based compound, diazonium based compound, acid imide sulphonic acid ester based compound etc. more.
Among the present invention, Photoepolymerizationinitiater initiater can use separately or mix more than 2 kinds and use.As Photoepolymerizationinitiater initiater, be preferably selected from least a in thioxanthones based compound, acetophenone based compound, bisglyoxaline based compound, triazine based compound, the O-acyl group oxime compound.
Among the preferred Photoepolymerizationinitiater initiater among the present invention, concrete example as the thioxanthones based compound, can enumerate thioxanthones, 2-clopenthixal ketone, 2-methyl thioxanthones, 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2,4-two clopenthixal ketones, 2,4-dimethyl thioxanthones, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthones etc.
And, as the concrete example of above-mentioned acetophenone based compound, can enumerate 2-methyl isophthalic acid-(4-(methyl mercapto) phenyl)-2-morpholinyl propane-1-ketone, 2-benzyl-2-dimethylamino-1-(4-morpholinyl phenyl) butane-1-ketone, 2-(4-methyl-benzyl)-2-(dimethylamino)-1-(4-morpholinyl phenyl) butane-1-ketone etc.
And,, can enumerate 2,2 '-two (2-chlorphenyls)-4 as the concrete example of above-mentioned bisglyoxaline based compound, 4 ', 5,5 '-tetraphenyl-1,2 '-bisglyoxaline, 2,2 '-two (2, the 4-dichlorophenyl)-4,4 ', 5,5 '-tetraphenyl-1,2 '-bisglyoxaline, 2,2 '-two (2,4, the 6-trichlorophenyl)-4,4 ', 5,5 '-tetraphenyl-1,2 '-bisglyoxaline etc.
Need to prove, when using the bisglyoxaline based compound, consider preferred from the aspect that can improve light sensitivity and use hydrogen donor as Photoepolymerizationinitiater initiater.Said herein " hydrogen donor " is meant the compound that can supply with hydrogen atom to the free radical that is produced by the bisglyoxaline based compound by exposure.As hydrogen donor, can enumerate for example 2-mercaptobenzothiazole, 2-sulfydryl benzo
Figure BSA00000389892800191
Mercaptan such as azoles are hydrogen donor, 4, and amine such as 4 '-two (dimethylamino) benzophenone, 4,4 '-two (lignocaine) benzophenone are hydrogen donor.Among the present invention, hydrogen donor can use separately or mix more than 2 kinds and use, consider from the aspect that can further improve light sensitivity, and preferably be that hydrogen donor and the amine more than a kind are that hydrogen donor is used in combination with the mercaptan more than a kind.
And, concrete example as above-mentioned triazine based compound, can enumerate 2,4,6-three (trichloromethyl) s-triazine, 2-methyl-4,6-two (trichloromethyl) s-triazine, 2-(2-(5-methylfuran-2-yl) vinyl)-4,6-two (trichloromethyl) s-triazine, 2-(2-(furans-2-yl) vinyl)-4,6-two (trichloromethyl) s-triazine, 2-(2-(4-lignocaine-2-aminomethyl phenyl) vinyl)-4,6-two (trichloromethyl) s-triazine, (2-(3 for 2-, the 4-Dimethoxyphenyl) vinyl)-4,6-two (trichloromethyl) s-triazine, 2-(4-methoxyphenyl)-4,6-two (trichloromethyl) s-triazine, 2-(4-ethoxybenzene vinyl)-4,6-two (trichloromethyl) s-triazine, 2-(4-n-butoxy phenyl)-4,6-two (trichloromethyl) s-triazine etc. has the triazine based compound of halogenated methyl.
And; concrete example as O-acyl group oxime compound; can enumerate 1; 2-octadione-1-(4-(thiophenyl) phenyl)-2-(O-benzoyl oxime), ethyl ketone-1-[9-ethyl-6-(2-methyl benzoyl)-9H-carbazole-3-yl]-1-(O-acetyl oxime), ethyl ketone-1-(9-ethyl-6-(2-methyl-4-tetrahydrofuran base methoxybenzoyl base)-9H-carbazole-3-yl)-1-(O-acetyl group oxime), ethyl ketone-1-(9-ethyl-6-{2-methyl-4-(2; 2-dimethyl-1, the 3-dioxolanyl) the methoxybenzoyl base }-9H-carbazole-3-yl)-1-(O-acetyl oxime) etc.
Among the present invention, when using the Photoepolymerizationinitiater initiater beyond the bisglyoxaline based compound such as acetophenone based compound, also can and use sensitizer.As such sensitizer; for example can enumerate 4; 4 '-two (dimethylamino) benzophenone, 4; 4 '-two (lignocaine) benzophenone, 4-lignocaine acetophenone, 4-dimethylamino propiophenone, 4-dimethyl ethyl aminobenzoate, 4-dimethylaminobenzoic acid-2-Octyl Nitrite, 2,5-two (4-lignocaine benzal) cyclohexanone, 7-lignocaine-3-(4-lignocaine benzoyl) cumarin, 4-(lignocaine) chalcone etc.
Among the present invention, with respect to 100 mass parts (B) crosslinking chemical, the content of Photoepolymerizationinitiater initiater is generally 0.01～120 mass parts, is preferably 1～100 mass parts.
-additive component-
Resin combination of the present invention also can further contain various additive components as required.
As above-mentioned additive component, for example can enumerate:
Vinyltrimethoxy silane, vinyltriethoxysilane, vinyl three (2-methoxy ethoxy) silane, N-(2-amino-ethyl)-3-aminopropyl methyl dimethoxysilane, N-(2-amino-ethyl)-3-TSL 8330, the 3-aminopropyltriethoxywerene werene, the 3-glycidoxy-propyltrimethoxy silane, 3-epoxypropoxy methyl dimethoxysilane, 2-(3, the 4-epoxycyclohexyl) ethyl trimethoxy silane, the 3-chloropropylmethyldimethoxysilane, the 3-r-chloropropyl trimethoxyl silane, the 3-methyl allyl acyloxypropyl trimethoxysilane, driving fit promoter such as 3-sulfydryl propyl trimethoxy silicane;
2, antioxidants such as 2-thiobis (4-methyl-6-tert butyl phenol), 2,6 di t butyl phenol;
Ultraviolet light absorbers such as 2-(the 3-tert-butyl group-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, alkoxy benzophenone class;
Anticoalescents such as sodium polyacrylate;
1,1 '-azo two (1-cyclohexanenitrile), 2-phenylazos-4-methoxyl-2, thermal free radical initiators such as 4-methyl pentane nitrile;
Ink-jet discharging performance stabilizing agents such as methyl alcohol, ethanol, isopropyl alcohol, normal butyl alcohol, glycerine etc.
And then coloured composition of the present invention can contain the thermal acid generator.Ripe acid producing agent is acidic composition by heating, for example can enumerate sulphur
Figure BSA00000389892800201
Salt, benzothiazole
Figure BSA00000389892800202
Salt, ammonium salt, phosphorus
Figure BSA00000389892800203
Salt etc.
Figure BSA00000389892800204
Salt.Among these thermal acid generators, preferred sulphur
Figure BSA00000389892800205
Salt and benzothiazole Salt.
As sulphur
Figure BSA00000389892800207
Salt and benzothiazole
Figure BSA00000389892800208
The object lesson of salt can be enumerated 4-acetoxyl group phenyl dimethyl disulfide Hexafluoro arsenate, 4-hydroxy phenyl benzyl methyl sulphur
Figure BSA000003898928002010
Hexafluoro antimonate, 4-acetoxyl group phenyl benzyl methyl sulphur
Figure BSA000003898928002011
Hexafluoro antimonate, 4-hydroxy phenyl dibenzyl sulfide
Figure BSA000003898928002012
Hexafluoro antimonate, 4-acetoxyl group phenyl dibenzyl sulfide
Figure BSA000003898928002013
Hexafluoro antimonate, 3-benzyl benzothiazole Hexafluoro antimonate etc.
Above-mentioned thermal acid generator can use separately or mix more than 2 kinds and use.
Among the present invention, coloured composition can prepare by suitable method, for example can prepare by (A)～(E) composition is mixed together with other compositions that add arbitrarily.Preparation method as preferred coloured composition, can enumerate following method: in (E) solvent, in the presence of spreading agent, for example use ball mill, roller mill etc. with (A) colorant, pulverize with a part (C) composition as required and mix, disperse, make colorant dispersion, then, in this colorant dispersion, add (B)～(D) composition and (E) solvent that further appends as required or other compositions, and mix, prepare thus.
Color filter
Color filter of the present invention has the dyed layer that uses coloured composition of the present invention to form.
As the method for making color filter, the first, can enumerate following method.At first, on the surface of substrate, form light shield layer (black matrix) in the mode that the part that forms pixel is divided as required.Then, coating for example is dispersed with the fluid composition of the colored radiation-sensitive composition of the present invention of red stain on this substrate, carries out prebake then, makes solvent evaporation, and formation is filmed.Then, by photomask to this exposure of filming after, use alkaline-based developer to develop, unexposed the dissolving of filming removed.Thereafter, by after cure, form the pel array that the red pixel pattern is arranged with the regulation alignment arrangements.
Then, use is dispersed with the fluid composition of each colored radiation-sensitive composition of green or blue colorant, with the above-mentioned coating of similarly carrying out each fluid composition, prebake, exposure, development and after cure, on same substrate, form green pel array and blue pixels array successively.
Thus, can obtain on substrate, disposing the color filter of redness, green and blue trichromatic pel array.But among the present invention, the order that forms each color pixel is not limited to said sequence.
Need to prove, black matrix can by utilize photoetching process will be by sputter or evaporation and the metallic film of chromium of film forming etc. make desired pattern and form, but also can use the colored radiation-sensitive composition that is dispersed with black colorant, similarly operate forming with the situation of above-mentioned pixel formation.Thickness by the film formed black matrix of metal foil is generally 0.1～0.2 μ m, and on the other hand, using the thickness of the resin black matrix of black radiation-ray sensitive composition formation is about 1 μ m.
The substrate that uses during as the formation color filter can be enumerated for example glass, silicon, polycarbonate, polyester, aromatic polyamide, polyamidoimide, polyimide etc.
And, as required, also suitable pre-treatment such as the chemical treatments that can implement in advance to utilize silane coupling agent etc. to carry out to these substrates, Cement Composite Treated by Plasma, ion plating, sputter, gas-phase reaction method, vacuum evaporation.
When the fluid composition of radiation-ray sensitive composition is coated substrate, can adopt suitable rubbing methods such as spray-on process, rolling method, method of spin coating (spin-coating method), slit die rubbing method, scraper rubbing method, preferred especially spin-coating method, slit die rubbing method.
Prebake makes up drying under reduced pressure usually and heat drying carries out.Drying under reduced pressure proceeds to usually and reaches 0.1～1Torr.In addition, drying was about 1～10 minute under the condition of heat drying was generally 70～110 ℃.
Coating thickness is with dried film thickness gauge, is generally 0.1～10 μ m, is preferably 0.2～8.0 μ m, the spy is preferably 0.2～6.0 μ m in addition.
The light source of the radioactive ray that use during as the formation color filter can be enumerated for example lamp source such as xenon lamp, Halogen lamp LED, tungsten lamp, high-pressure sodium lamp, ultrahigh pressure mercury lamp, metal halide lamp, medium pressure mercury lamp, low pressure mercury lamp; LASER Light Source such as argon laser, YAG laser, XeCl excimer laser, nitrogen laser etc., but optimal wavelength is at the radioactive ray of 190～450nm scope.
The exposure of radioactive ray is preferably 10～10,000J/m 2
And, as above-mentioned alkaline-based developer, preference such as sodium carbonate, NaOH, potassium hydroxide, tetramethyl ammonium hydroxide, choline, 1,8-diazabicyclo [5.4.0]-7-undecylene, 1, the aqueous solution of 5-diazabicyclo [4.3.0]-5-nonene etc.
In above-mentioned alkaline-based developer, also can add an amount of water-miscible organic solvent such as for example methyl alcohol, ethanol etc., surfactant etc.Need to prove, wash usually after the alkaline development.
As the development treatment method, can be suitable for spray development method, spray development method, immersion development method, soak and put (puddle) development method etc.Development conditions preferably 5～300 seconds at normal temperatures.
After the condition of curing be generally at 180～280 ℃ and handled about 10～60 minutes.
The thickness of the pixel of Xing Chenging is generally 0.5～5.0 μ m, is preferably 1.0～3.0 μ m like this.
And, as second method of making color filter, the also known method that obtains each color pixel by ink-jetting style.In this method, at first, on the surface of substrate, form the next door that has shade function concurrently.Then, in formed next door, utilize ink discharge device to discharge for example to be dispersed with the fluid composition of coloured composition of the present invention of red stain after, carry out prebake, make solvent evaporation.Then, as required to this film expose after, by after cure it solidified, form red pattern of pixels.
Then, use the fluid composition of each coloured composition that is dispersed with green or blue colorant,, on same substrate, form green pattern of pixels and blue pixels pattern successively with above-mentioned operation similarly.Thus, can obtain on substrate, disposing the color filter of redness, green and blue trichromatic pattern of pixels.But in the present invention, the order that forms each color pixel is not limited to said sequence.
Need to prove that shade function is not only brought into play in above-mentioned next door, but also performance is used to make the not function of colour mixture of the coloured composition of all kinds that is discharged in the institute zoning, so compare with the employed black matrix of above-mentioned first method, thickness is thick.Its thickness is generally 1～3 μ m.Therefore, use the black radiation-ray sensitive composition to form the next door usually.
The substrate that uses when forming color filter, the light source of radioactive ray or prebake, after the method for curing identical with condition with the first above-mentioned method.Like this, the thickness of the pixel that forms by ink-jetting style and the thickness in next door are same degree.
Coloured composition of the present invention can be formed in by ink-jetting style and does not produce the pixel that coating is left over partly, flatness is extremely excellent in the next door.And, even only by after cure when solidifying, also can form pixel with extremely excellent solvent resistance.And the pixel of utilizing coloured composition of the present invention to form has extremely excellent thermotolerance, so even carry out high temperature after cure, the transparency and color characteristics can not descend yet.Therefore, coloured composition of the present invention is particularly suitable for utilizing the formation of the dyed layer that ink-jetting style carries out.
Color filter of the present invention is because the transparency and color characteristics excellence, so exceedingly useful to the color liquid crystal display arrangement of transmission-type or reflection-type and solid-state imager, organic EL display element, Electronic Paper etc.
Display element
Display element of the present invention possesses color filter of the present invention.As display element, can enumerate color liquid crystal display device, organic EL display element, Electronic Paper etc.
The liquid crystal display cells that possesses color filter of the present invention can adopt suitable structure.For example, can adopt: form above-mentioned color filter on the substrate different with the driving usefulness substrate that disposes thin film transistor (TFT) (TFT), driving is with substrate and be formed with the substrate of color filter across the opposed structure of liquid crystal layer.And then, also can adopt: dispose the substrate that is formed with color filter on the surface of driving with substrate of thin film transistor (TFT) (TFT), be formed with the substrate of ITO (indium oxide of doped tin) electrode across the opposed structure of liquid crystal layer.The advantage that a kind of structure in back has can significantly improve aperture opening ratio, obtain the liquid crystal indicator of bright and high-resolution.
And the organic EL display element that possesses color filter of the present invention can adopt suitable structure, for example can enumerate disclosed structure in Japanese kokai publication hei 11-307242 communique.
And the Electronic Paper that possesses color filter of the present invention can adopt suitable structure, for example can enumerate disclosed structure in the TOHKEMY 2007-41169 communique.
Embodiment
Below, enumerate embodiment and be described more specifically embodiments of the present invention.But, the invention is not restricted to following embodiment.
The preparation of colorant dispersion
Preparation example 1
With 13.0 mass parts as C.I. paratonere 254,7.5 mass parts of (A) colorant as the Adisper PB880 (manufacturing of aginomoto fine chemistry Co., Ltd.) of spreading agent and 79.5 mass parts as 1 of (E) solvent, 3-butylene glycol diacetate esters utilizes ball mill to handle, preparation colorant dispersion (R1).
Preparation example 2
With 13.0 mass parts be as the object of the C.I. paratonere 254/C.I. paratonere 177/ above-mentioned formula (II) of (A) colorant expression specific yellow uitramarine=25/47/28 (mass ratio) potpourri, 7.5 mass parts of melamine as the Adisper PB880 (manufacturing of aginomoto fine chemistry Co., Ltd.) of spreading agent and 79.5 mass parts as 1 of (E) solvent, 3-butylene glycol diacetate esters utilizes ball mill to handle, preparation colorant dispersion (R2).
Preparation example 3
With 13.0 mass parts as C.I. paratonere 242/C.I. paratonere 177=40/60 (mass ratio) potpourri of (A) colorant, 7.5 mass parts as the Adisper PB880 (manufacturing of aginomoto fine chemistry Co., Ltd.) of spreading agent and 79.5 mass parts as 1 of (E) solvent, 3-butylene glycol diacetate esters utilizes ball mill to handle, preparation colorant dispersion (R3).
Preparation example 4
With 13.0 mass parts be as the object of the C.I. naphthol green 58/ above-mentioned formula (II) of (A) colorant expression specific yellow uitramarine=60/40 (mass ratio) potpourri, 6.9 mass parts of melamine as the Adisper PB881 (manufacturing of aginomoto fine chemistry Co., Ltd.) of spreading agent and 80.1 mass parts as 1 of (E) solvent, 3-butylene glycol diacetate esters utilizes ball mill to handle, preparation colorant dispersion (G1).
Preparation example 5
Is specific yellow uitramarine=65/35 (mass ratio) potpourri of melamine, 6.9 mass parts as the Adisper PB881 (manufacturing of aginomoto fine chemistry Co., Ltd.) of spreading agent and 80.1 mass parts as 1 of (E) solvent with 13.0 mass parts as the object of the C.I. pigment green 36 of (A) colorant/above-mentioned formula (II) expression, 3-butylene glycol diacetate esters utilizes ball mill to handle, preparation colorant dispersion (G2).
Preparation example 6
With the C.I. pigment blue 15 of 12.0 mass parts as (A) colorant: 6/C.I. pigment Violet 23=83/17 (mass ratio) potpourri, 6.8 mass parts as the Adisper PB821 (manufacturing of aginomoto fine chemistry Co., Ltd.) of spreading agent and 81.2 mass parts as 1 of (E) solvent, 3-butylene glycol diacetate esters utilizes ball mill to handle, preparation colorant dispersion (B1).
Synthesizing of resin glue
In the flask that possesses condenser pipe, stirring machine, add 3 mass parts 2,2 '-azoisobutyronitrile and 200 mass parts diethylene glycol monobutyl ether acetic acid esters then add 10 mass parts methacrylic acids, 25 mass parts N-phenylmaleimides, 15 mass parts styrene, 40 mass parts diethylene glycol methyl ether methacrylates (Japan Oil Co's manufacturing, trade name: BLEMMER RPME-100), 10 mass parts dihydro bicyclic pentadiene acrylate and 5 mass parts are as the α-Jia Jibenyixierjuwu of molecular weight regulator, carry out the nitrogen displacement.Thereafter slowly stir, making the temperature rising of reaction solution is 80 ℃, keeps this temperature to carry out polymerization in 5 hours, obtains resin glue solution (Gu forming branch concentration=29.8%) thus.The resin glue Mw=8 that obtains, 200, Mn=3300.With this resin glue solution as " resin solution 1 ".
Embodiment 1
With 567 mass parts as the colorant dispersion (R1) of (A) colorant, 25 mass parts R with above-mentioned formula (b1-4) as (B) crosslinking chemical 11～R 16PF-7002 (the R in the above-mentioned formula (1-1) that all to be the compound of methyl make as the OMNOVA company of surfactant (D) as resin solution 1,0.9 mass parts of (C) resin glue as the reaction product of the crosslinking chemical of major component (three and chemical company's manufacturing, trade name MW-30, weight average degree of polymerization 1.3), 7 mass parts dipentaerythritols, five acrylate and succinic anhydride, 18 mass parts dipentaerythritol acrylates, 111 mass parts 21And R 22Be CF 3CF 2CF 2CF 2CH 2CH 2-, R 23And R 24Surfactant for methyl, m+n=4～5) and 272 mass parts mix preparation coloured composition (IJ-1) as the 1,3 butylene glycol diacetate esters of solvent.
For coloured composition (IJ-1), estimate according to following main points.Evaluation result is shown in table 2.
The evaluation of color characteristics
Adopt spin coater that coloured composition (IJ-1) is coated on the soda-lime glass substrate, carry out vacuum drying with 0.2Torr then, on 90 ℃ hot plate, carry out 5 minutes prebake, in 230 ℃ cleaning oven, carry out again curing after 30 minutes, form cured film.
To the cured film that obtains, adopt color analysis instrument (Otsuka Electronics Co., Ltd. to make MCPD2000), with illuminant-C, the 2 degree visuals field measure chromaticity coordinate value in the CIE color specification systems (x, y) and values (Y).And,, adopt the mensuration of contrast meter (CT-1, Blank20000 that kettle slope motor company makes) degree of comparing to the cured film that obtains.And the α-step IQ that uses KLA-Tencor to make measures the thickness of resulting cured film.
The evaluation of solvent resistance
It is square that glass substrate that make, that be formed with cured film in the above-mentioned color characteristics evaluation is cut into 2cm * 4cm, makes test film.Resulting test film is immersed in 25 ℃ the N-Methyl pyrrolidone 30 minutes, obtains the change color Δ Eab before and after the dipping *For solvent resistance, Δ Eab *Be evaluated as during less than 3 well, it is very good to be evaluated as during less than 2.5.
Stable on heating evaluation
It is square that glass substrate that make, that be formed with cured film in the above-mentioned color characteristics evaluation is cut into 2cm * 4cm, makes test film.The test film that obtains was heated 1 hour in 250 ℃ cleaning oven, obtain the change color Δ Eab of heating front and back *For thermotolerance, Δ Eab *Be evaluated as during less than 5 well, it is very good to be evaluated as during less than 3.
The evaluation of pixel flatness and coating ductility
Use ink discharge device Nanoprinter-1500S (manufacturing of Microjet Co., Ltd.), in the pixel that the next door of height 2.0 μ m, length 500 μ m, width 150 μ m is divided, be that the mode of 2.0 μ m is discharged coloured composition according near the thickness the pixel center after the drying.After carrying out vacuum drying with 0.2Torr, on 90 ℃ heating plate, carry out 5 minutes prebake, in 230 ℃ cleaning oven, carry out again curing after 30 minutes.Use α-step IQ (manufacturing of KLA Tencor company), at the thickness of Width and length direction mensuration pixel central portion.
At this moment, the maximal value of the thickness of Width is made as A, the thickness at pixel two ends is made as B, C, obtain Δ H=A-(B+C)/2.For the flatness of pixel, be evaluated as during this value less than 0.60 μ m well, it is very good to be evaluated as during less than 0.40 μ m.
And, measure the horizontal range Δ L of the point of comfortable length direction thickness maximum and nearest pixel end to the pixel end.For coating ductility, this value is that 50 μ m are evaluated as when following well, and it is very good that this value is that 30 μ m are evaluated as when following.
The evaluation of granularity
Use the viscosity (25 ℃) of the ELD type viscometer determining coloured composition of Tokyo Keiki Inc.'s manufacturing.
Capillary evaluation
Use Dynometer (manufacturing of BYK-Gardner GmbH company) to measure the surface tension of coloured composition.
Embodiment 2～12 and comparative example 1～6
Except the kind of the constituent among the embodiment 1 and amount are changed into as shown in table 1, operation similarly to Example 1, preparation resin combination (IJ-2)～(IJ-18).Composition is separately listed in table 1.
Then, use resin combination (IJ-2)～(IJ-18) to replace resin combination (IJ-1) respectively, estimate similarly to Example 1 in addition.Evaluation result is listed in table 2.
Each composition in the table 1 is as follows.
MW-30: with the R of above-mentioned formula (b1-4) 11～R 16All be the compound of methyl as the crosslinking chemical of major component (three and chemical company's manufacturing, trade name MW-30, weight average degree of polymerization 1.3)
B2-1: the reaction product of dipentaerythritol five acrylate and succinic anhydride
B2-2: dipentaerythritol five acrylate
B2-3: dipentaerythritol acrylate
PF-7002: R in the above-mentioned formula (1-1) 21And R 22Be CF 3CF 2CF 2CF 2CH 2CH 2-, R 23And R 24Surfactant (manufacturing of OMNOVA company) for methyl, m+n=4～5
F475: the fluorine that does not have hydroxyl is surfactant (manufacturing of DIC company)
FT-250: the fluorine that does not have hydroxyl is surfactant (manufacturing of NEOS company)
1,3-BGDA:1,3-butylene glycol diacetate esters
BCTAC: diglycol monotertiary n-butyl ether acetic acid esters
[table 1]
Figure BSA00000389892800291
[table 2]
Figure BSA00000389892800301

Claims (7)

1. a coloured composition is characterized in that, contains the compound and the E solvent of A colorant, B crosslinking chemical, C resin glue, the following formula of D (1) expression,
Figure FSA00000389892700011
In the formula (1), R 21And R 22Expression independently of each other has the group of fluoro-alkyl, R 23And R 24Represent methyl or ethyl independently of each other, X represents not fluorine-containing divalent linking group, and m and n represent 1～100 integer independently of each other.
2. coloured composition as claimed in claim 1, wherein, in the described formula (1), R 21And R 22Be group independently of each other with perfluoroalkyl of carbon number 1～4.
3. coloured composition as claimed in claim 1, wherein, in the described formula (1), m+n is 2～40.
4. coloured composition as claimed in claim 1, wherein, in the described formula (1), X is the divalent alkyl of carbon number 1～20.
5. as each described coloured composition in the claim 1～4, it is used to utilize the formation of the dyed layer that ink-jetting style carries out.
6. color filter, it possesses the dyed layer that uses each described coloured composition in the claim 1～5 and form.
7. display element, it possesses the described color filter of claim 6.
CN2010105882170A 2009-12-09 2010-11-30 Coloring composition, color filter and display element Pending CN102141730A (en)

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