CN103890658A - Photosensitive resin composition for color filter and color filter made by using the same - Google Patents

Photosensitive resin composition for color filter and color filter made by using the same Download PDF

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Publication number
CN103890658A
CN103890658A CN201280050041.0A CN201280050041A CN103890658A CN 103890658 A CN103890658 A CN 103890658A CN 201280050041 A CN201280050041 A CN 201280050041A CN 103890658 A CN103890658 A CN 103890658A
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methyl
acrylate
phthalocyanine
ethyl
carbon number
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CN103890658B (en
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金吉来
金敬娥
朴正焕
金炳郁
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Dongjin Semichem Co Ltd
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Dongjin Semichem Co Ltd
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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • 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
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/0042—Photosensitive materials with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists
    • 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
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

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

Abstract

The present invention relates to a photosensitive resin composition for a color filter and a color filter manufactured using the same. The photosensitive resin composition for a color filter according to the present invention comprises a dye having specific spectral characteristics and a pigment, whereby the color filter manufactured using the composition has excellent light transmittance, brightness, contrast, and color purity, and has good heat resistance.

Description

For the photosensitive polymer combination of colored filter and the colored filter that uses said composition to make
Technical field
The colored filter that the present invention relates to a kind of photosensitive polymer combination for colored filter and use said composition to make.
Background technology
Colored filter is used for the optical lightscreening device of liquid crystal display, organic light emitting apparatus, video camera etc., and colored filter normally utilizes the method manufacturings such as decoration method (staining), print process (printing), electrodeposition process (electrodeposition), Pigments method (pigment dispersion).
The most general practice of aforementioned Pigments method be by Pigments in having in photosensitive composition in 200 to 400nm wavelength coverages, recycling light shield etching method is manufactured colored filter.
Because aforementioned Pigments method is used pigment, be therefore stable to light or heat etc., so can utilize relatively simple technique to manufacture colored filter.And aforementioned Pigments method can be by dwindling the particle diameter of pigment and controlling dispersion degree and control brightness and contrast.
But, in Pigments method, improve colour purity if increase pigment content, brightness and contrast may relatively reduce, and foregoing problems cannot only solve by the particle diameter of controlling pigment.
Therefore,, as the method for the restriction in order to overcome aforementioned Pigments method, be a kind ofly suggested by the method that dyestuff substitutes pigment.
But because dyestuff is insoluble in solvent, therefore the used content of dyestuff is restricted.Although someone advises by for example improving colorant dissolubility etc. various for improving the method for dyestuff content, but in the time that dyestuff content is high, after baking, dyestuff may be separated out or thermotolerance may reduce, so that reduces the problems such as transmittance and but still exist.
Summary of the invention
Therefore, an object of the present invention is to provide a kind of photosensitive polymer combination, and it can be manufactured one and have excellent transmittance, brightness, contrast and colour purity, and has the colored filter of good heat resistance.
Another object of the present invention is to provide a kind of colored filter that uses foregoing to make.
According to one embodiment of the invention, a kind of photosensitive polymer combination for colored filter is provided, it comprises binder resin; Reactive unsaturated compound; Blue pigment; There is in 430 to 465nm wavelength coverages the transmittance that is equal to or higher than 90%, and there is the dyestuff of the transmittance that is equal to or less than 55% in 495 to 505nm wavelength coverages; Polymerization initiator; And solvent.
According to another embodiment of the present invention, provide a kind of photosensitive polymer combination for colored filter, it comprises binder resin; Reactive unsaturated compound; Viridine green; There is in 530 to 540nm wavelength coverages the transmittance that is equal to or higher than 95%, and there is the dyestuff of the transmittance that is equal to or less than 55% in 580 to 590nm wavelength coverages; Polymerization initiator; And solvent.
In the composition of above-described embodiment, described dyestuff can be a kind of compound being represented by following Chemical formula 1:
[Chemical formula 1]
Figure BDA0000489795300000021
In described Chemical formula 1,
M is copper, cobalt, aluminium, zinc, nickel, platinum or chromium;
N is nitrogen;
R 1to R 16be hydrogen atom, halogen atom, carboxyl, hydroxyl, sulfonic group, the sulfonic alkyl being replaced by a heterocyclic radical, sulfonic acid hydroxyl, sulfonic acid alkoxy, sulfonic acid aryl, the alkyl of carbon number 1 to 20, the naphthenic base of carbon number 3 to 20, the aryl of carbon number 6 to 20, assorted alkyl, the Heterocyclylalkyl of carbon number 3 to 20 or the heteroaryl of carbon number 3 to 20 of carbon number 1 to 20 independently of one another.
Described dyestuff preferably can be a kind of compound being represented by following Chemical formula 2:
[Chemical formula 2]
Figure BDA0000489795300000031
In described Chemical formula 2,
M is copper, cobalt, aluminium, zinc, nickel, platinum or chromium;
N is nitrogen;
O is oxygen;
R ato R hbe the alkyl of carbon number 1 to 20, the naphthenic base of carbon number 3 to 20, the aryl of carbon number 6 to 20, assorted alkyl, the Heterocyclylalkyl of carbon number 3 to 20 or the heteroaryl of carbon number 3 to 20 of carbon number 1 to 20 independently of one another.
In addition, have at 430 to 465nm wavelength coverage transmittances and be equal to or higher than 90%, and be equal to or less than the dyestuff of 55% spectral characteristic at 495 to 505nm wavelength coverage transmittances, be preferably and be selected from eight (2-ethyl hexyl oxy) copper phthalocyanine (Octa (2-ethylhexyloxy) Cu Phthalocyanine), eight (2-ethyl hexyl oxy) cobalt phthalocyanine (Octa (2-ethylhexyloxy) Co Phthalocyanine), eight (2-ethyl hexyl oxy) aluminium phthalocyanine (Octa (2-ethylhexyloxy) Al Phthalocyanine), eight (2-ethyl hexyl oxy) ZnPc (Octa (2-ethylhexyloxy) Zn Phthalocyanine), eight (2-ethyl hexyl oxy) nickel phthalocyanine (Octa (2-ethylhexyloxy) Ni Phthalocyanine), eight (2-ethyl hexyl oxy) platinum phthalocyanine (Octa (2-ethylhexyloxy) Pt Phthalocyanine), and at least one compound in eight (2-ethyl hexyl oxy) chromium phthalocyanine (Octa (2-ethylhexyloxy) Cr Phthalocyanine).
In addition, have at 530 to 540nm wavelength coverage transmittances and be equal to or higher than 95%, and be equal to or less than the dyestuff of 55% spectral characteristic at 580 to 590nm wavelength coverage transmittances, be preferably and be selected from eight (1, 4, 7, 10-tetra-oxa-undecyls) copper phthalocyanine (Octa (1, 4, 7, 10-tetraoxaundecyl) Cu Phthalocyanine), eight (1, 4, 7, 10-tetra-oxa-undecyls) cobalt phthalocyanine (Octa (1, 4, 7, 10-tetraoxaundecyl) Co Phthalocyanine), eight (1, 4, 7, 10-tetra-oxa-undecyls) aluminium phthalocyanine (Octa (1, 4, 7, 10-tetraoxaundecyl) Al Phthalocyanine), eight (1, 4, 7, 10-tetra-oxa-undecyls) ZnPc (Octa (1, 4, 7, 10-tetraoxaundecyl) Zn Phthalocyanine), eight (1, 4, 7, 10-tetra-oxa-undecyls) nickel phthalocyanine (Octa (1, 4, 7, 10-tetraoxaundecyl) NiPhthalocyanine), eight (1, 4, 7, 10-tetra-oxa-undecyls) platinum phthalocyanine (Octa (1, 4, 7, 10-tetraoxaundecyl) Pt Phthalocyanine), and eight (1, 4, 7, 10-tetra-oxa-undecyls) chromium phthalocyanine (Octa (1, 4, 7, 10-tetraoxaundecyl) Cr Phthalocyanine) at least one compound.
Meanwhile, the photosensitive polymer combination for colored filter of above-described embodiment, with respect to the described binder resin of 100 weight portions, can comprise:
The described reactive unsaturated compound of 100 to 250 weight portions;
The described pigment of 5 to 150 weight portions;
The described dyestuff of 50 to 250 weight portions;
The described polymerization initiator of 5 to 50 weight portions; And
The described solvent of 100 to 500 weight portions.
Described binder resin can be a co-polymer, by 10 to 40wt% at least one have and be selected from (methyl) acrylic acid ((meth) acrylic acid), Yi Kang acid (itaconic acid), maleic acid (maleic acid), fumaric acid (fumaric acid), vinyl acetic acid (vinyl acetic acid), 2-acrylyl oxy-ethyl phthalandione hydrogen ester (2-acryloyloxyethyl hydrogen phthalate), and the monomer of ethene acidic group in 2-acryloyl-oxy propyl group phthalandione hydrogen ester (2-acryloyloxypropyl hydrogen phthalate), with 60 to 90wt% at least one be selected from (methyl) isobutyl acrylate (isobutyl (meth) acrylate), (methyl) tert-butyl acrylate (tert-butyl (meth) acrylate), (methyl) acrylic acid Lauryl Ester (lauryl (meth) acrylate), ste(methyl) aryl-acrylic acid esters (ste (meth) arylacrylate), (methyl) cyclohexyl acrylate (cyclohexyl (meth) acrylate), (methyl) isobornyl acrylate (isobonyl (meth) acrylate), (methyl) benzyl acrylate (bezyl (meth) acrylate), (methyl) acrylic acid 2-hydroxy alkyl ester (2-hydroxyalkyl (meth) acrylate), (methyl) acrylic acid trimethoxy butyl ester (trimethoxybutyl (meth) acrylate), ethyl carbitol (methyl) acrylate (ethylcarbitol (meth) acrylate), (methyl) phenoxyethyl acrylate (phenoxyethyl (meth) acrylate), (methyl) acrylic acid 4-hydroxyl butyl ester (4-hydroxybutyl (meth) acrylate), phenoxy group ethylene glycol (methyl) acrylate (phenoxyethyleneglycol (meth) acrylate), (methyl) HEA (2-hydroxyethyl (meth) acrylate), (methyl) acrylic acid 2-hydroxypropyl ester (2-hydroxypropyl (meth) acrylate), 2-acryloxy ethyl 2-hydroxypropyl (methyl) phthalic ester (2-acryloxyethyl 2-hydroxypropyl (meth) phthalate), 2-hydroxyl-3-phenoxy propyl (methyl) acrylate (2-hydroxy-3-phenoxypropyl (meth) acrylate), triethyl siloxy ethyl (methyl) methyl acrylate (triethylsiloxylethyl (meth) acrylate), and (methyl) acrylate monomer in ethyl triethylene glycol (methyl) acrylate (ethyltriglycol (meth) acrylate) is polymerized.
And, described reactive unsaturated compound can be and is selected from ethylene glycol bisthioglycolate (methyl) acrylate (ethyleneglycol di (meth) acrylate), diethylene glycol two (methyl) acrylate (diethyleneglycol di (meth) acrylate), triethylene glycol two (methyl) acrylate (triethyleneglycol di (meth) acrylate), propylene glycol two (methyl) acrylate (propyleneglycol di (meth) acrylate), 1,4-butylene glycol two (methyl) acrylate (1,4-butandiol di (meth) acrylate), 1,6-hexanediol two (methyl) acrylate (1,6-hexanediol di (meth) acrylate), neopentyl glycol two (methyl) acrylate (neopentylglycol di (meth) acrylate), pentaerythrite two (methyl) acrylate (pentaerythritol di (meth) acrylate), pentaerythrite three (methyl) acrylate (pentaerythritol tri (meth) acrylate), pentaerythrite four (methyl) acrylate (pentaerythritol tetra (meth) acrylate), pentaerythrite five (methyl) acrylate (pentaerythritol penta (meth) acrylate), pentaerythrite six (methyl) acrylate (pentaerythritol hexa (meth) acrylate), dipentaerythritol two (methyl) acrylate (dipentaerythritol di (meth) acrylate), dipentaerythritol three (methyl) acrylate (dipentaerythritol tri (meth) acrylate), dipentaerythritol four (methyl) acrylate (dipentaerythritol tetra (meth) acrylate), dipentaerythritol five (methyl) acrylate (dipentaerythritol penta (meth) acrylate), dipentaerythritol six (methyl) acrylate (dipentaerythritol hexa (meth) acrylate), bisphenol-A two (methyl) acrylate (bisphenol A di (meth) acrylate), trimethylolpropane tris (methyl) acrylate (trimethylolpropane tri (meth) acrylate), phenolic aldehyde epoxy (methyl) acrylate (novolacepoxy (meth) acrylate), there is dipentaerythritol five (methyl) acrylate (dipentaerythritol penta (meth) acrylate) derivant of carboxyl, oxirane glycerine trimethylolpropane tris (methyl) acrylate (ethyleneoxide glycerin trimethylolpropanetri (meth) acrylate), epoxypropane glycerine three (methyl) acrylate (propyleneoxide glycerin tri (meth) acrylate), epoxy (methyl) acrylate oligomer (epoxy (meth) acrylate oligomer), amido formate (methyl) acrylate oligomer (urethane (meth) acrylate oligomer), sulfydryl (methyl) acrylate oligomer (thiol (meth) acrylate oligomer), and at least one compound in polyester (methyl) acrylate oligomer (polyester (meth) acrylate oligomer).
According to another embodiment of the present invention, provide a kind of colored filter that uses above-mentioned photosensitive polymer combination to make.
Because the photosensitive polymer combination for colored filter of the present invention comprises dyestuff and the pigment with certain spectroscopic characteristics, therefore the colored filter that uses aforementioned photosensitive polymer combination to make has excellent transmittance, brightness, contrast and colour purity, and has good thermotolerance.
Brief description of the drawings
Fig. 1 a to Fig. 1 b and Fig. 2 a to Fig. 2 b show can make an addition to according to the spectrum character diagram of the pigment in the composition of the embodiment of the present invention and dyestuff.
Fig. 3 and Fig. 4 are the comparison spectrum performance plot that uses the colored filter that the composition of embodiment and comparative example makes.
The outward appearance enlarged photograph of the colored filter that the composition of Fig. 5 a to Fig. 5 b demonstration use embodiments of the invention is made.
Embodiment
Below, will photosensitive polymer combination according to an embodiment of the invention and the colored filter that uses this photosensitive polymer combination to make be described.
Except as otherwise noted, as the noun using in this instructions of giving a definition.
First, " (methyl) acrylic acid " typically refers to acrylic acid and/or methacrylic acid.
And " (methyl) acrylate " typically refers to acrylate and/or methacrylate.
And " alkyl " is defined as the alkyl that comprises carbon number 1 to 20; " naphthenic base " is defined as the naphthenic base that comprises carbon number 3 to 20; " aryl " is defined as the aryl that comprises carbon number 6 to 20; " assorted alkyl " is defined as the assorted alkyl that comprises carbon number 1 to 20; " Heterocyclylalkyl " is defined as the Heterocyclylalkyl that comprises carbon number 3 to 20; " heteroaryl " is defined as the heteroaryl that comprises carbon number 3 to 20.At this, " mixing " refers to that the atom that at least one carbon atom is selected from oxygen, sulphur, nitrogen, phosphorus, silicon and combination thereof replaces.
Simultaneously, inventor confirms at the research process repeatedly carrying out for the photosensitive polymer combination of colored filter, if when thering is the dyestuff collocation pigment of certain spectroscopic characteristics and using together, described photosensitive polymer combination can be made into and can show excellent transmittance, brightness, contrast and colour purity, and can show the colored filter of good heat resistance.
According to one embodiment of the invention, a kind of photosensitive polymer combination for colored filter is provided, it comprises binder resin; Reactive unsaturated compound; Blue pigment; There is in 430 to 465nm wavelength coverages the transmittance that is equal to or higher than 90%, and there is the dyestuff of the transmittance that is equal to or less than 55% in 495 to 505nm wavelength coverages; Polymerization initiator; And solvent.
According to another embodiment of the present invention, provide a kind of photosensitive polymer combination for colored filter, it comprises binder resin; Reactive unsaturated compound; Viridine green; There is in 530 to 540nm wavelength coverages the transmittance that is equal to or higher than 95%, and there is the dyestuff of the transmittance that is equal to or less than 55% in 580 to 590nm wavelength coverages; Polymerization initiator; And solvent.
The various constituents that below, explanation can be comprised according to the photosensitive polymer combination for colored filter of the embodiment of the present invention.
Binder resin
Binder resin is guaranteed the dispersion stabilization of pigment and dyestuff etc., makes can form the pixel of required resolution in developing process simultaneously.
Be not particularly limited for binder resin, can be selected from the normal binder resin using of resin combination for colored filter in the art.
According to one embodiment of the invention, described binder resin can be the co-polymer of at least one monomer with ethene acidic group and at least one (methyl) acrylate monomer.
Described binder resin can be the co-polymer of (methyl) acrylate monomer of 10 to 40wt% the monomer with ethene acidic group and 60 to 90wt%, be preferably the co-polymer of (methyl) acrylate monomer of 20 to 40wt% the monomer with ethene acidic group and 60 to 80wt%, more preferably the co-polymer of 25 to 35wt% the monomer with ethene acidic group and (methyl) acrylate monomer of 65 to 75wt%.
Particularly, if described in there is ethene acidic group the content of monomer in binder resin lower than 10wt%, the solubleness of photosensitive polymer combination in alkaline developer may reduce.And, if described in there is ethene acidic group the content of monomer in binder resin higher than 40wt%, in the developing process that uses alkaline developer, may produce bright spot (pattern loss) and tear phenomenon (tearing).And, if the content of described (methyl) acrylate monomer in binder resin is lower than 60wt%, in developing process, may reduce with the adhesion of substrate, cause the phenomenon of tearing of pattern to become flatness (straightness) variation serious and pattern that form.And, if the content of described (methyl) acrylate monomer in binder resin higher than 90wt%, the required time that develops may increase, so that reduces productive rate.
The described monomer with ethene acidic group can be and is selected from (methyl) acrylic acid ((meth) acrylic acid), Yi Kang acid (itaconic acid), maleic acid (maleic acid), fumaric acid (fumaric acid), vinyl acetic acid (vinyl acetic acid), at least one compound in 2-acrylyl oxy-ethyl phthalandione hydrogen ester (2-acryloyloxyethyl hydrogen phthalate) and 2-acryloyl-oxy propyl group phthalandione hydrogen ester (2-acryloyloxypropyl hydrogen phthalate).
In addition, described (methyl) acrylate monomer can be and is selected from (methyl) isobutyl acrylate (isobutyl (meth) acrylate), (methyl) tert-butyl acrylate (tert-butyl (meth) acrylate), (methyl) acrylic acid Lauryl Ester (lauryl (meth) acrylate), ste(methyl) aryl-acrylic acid esters (ste (meth) arylacrylate), (methyl) cyclohexyl acrylate (cyclohexyl (meth) acrylate), (methyl) isobornyl acrylate (isobonyl (meth) acrylate), (methyl) benzyl acrylate (bezyl (meth) acrylate), (methyl) acrylic acid 2-hydroxy alkyl ester (2-hydroxyalkyl (meth) acrylate), (methyl) acrylic acid trimethoxy butyl ester (trimethoxybutyl (meth) acrylate), ethyl carbitol (methyl) acrylate (ethylcarbitol (meth) acrylate), (methyl) phenoxyethyl acrylate (phenoxyethyl (meth) acrylate), (methyl) acrylic acid 4-hydroxyl butyl ester (4-hydroxybutyl (meth) acrylate), phenoxy group ethylene glycol (methyl) acrylate (phenoxyethyleneglycol (meth) acrylate), (methyl) HEA (2-hydroxyethyl (meth) acrylate), (methyl) acrylic acid 2-hydroxypropyl ester (2-hydroxypropyl (meth) acrylate), 2-acryloxy ethyl 2-hydroxypropyl (methyl) phthalic ester (2-acryloxyethyl 2-hydroxypropyl (meth) phthalate), 2-hydroxyl-3-phenoxy propyl (methyl) acrylate (2-hydroxy-3-phenoxypropyl (meth) acrylate), triethyl siloxy ethyl (methyl) methyl acrylate (triethylsiloxylethyl (meth) acrylate), and at least one compound in ethyl triethylene glycol (methyl) acrylate (ethyltriglycol (meth) acrylate).
In addition, consider and adhesion, the dispersion stabilization of adding ingredient etc. of substrate, preferably, described binder resin has 5,000 to 50,000 weight-average molecular weight (Mw).
Taking the general assembly (TW) of photosensitive polymer combination as base Huaihe River, the content of described binder resin can be 5 to 15wt%.Particularly, preferably, the content of described binder resin is equal to or higher than 5wt%, to show the minimum dispersion stabilization that has by the interpolation of binder resin, film strength, thermotolerance etc.And excessive if described binder resin uses, the stickiness of described photosensitive polymer combination can excessively increase and optical property, the physical property of reduction photosensitive polymer combination, and process efficiency.In order to improve this problem, preferably, the content of described binder resin is equal to or less than 15wt%.
Reactive unsaturated compound
Photosensitive polymer combination for colored filter according to the present invention comprises reactive unsaturated compound.Described reactive unsaturated compound is arranged in pairs or groups described binder resin and is given described photosensitive polymer combination stickiness and guarantee film strength.
Particularly, described reactive unsaturated compound optional from heat polymerization (thermal polymerization) or photopolymerization reaction (photopolymerization) monomer, heat polymerization or photopolymerization reaction oligomer, with and composition thereof.
Described heat polymerization or photopolymerization reaction monomer can be and be selected from ethylene glycol bisthioglycolate (methyl) acrylate (ethyleneglycol di (meth) acrylate), diethylene glycol two (methyl) acrylate (diethyleneglycol di (meth) acrylate), triethylene glycol two (methyl) acrylate (triethyleneglycol di (meth) acrylate), propylene glycol two (methyl) acrylate (propyleneglycol di (meth) acrylate), 1,4-butylene glycol two (methyl) acrylate (1,4-butanediol di (meth) acrylate), 1,6-hexanediol two (methyl) acrylate (1,6-hexanediol di (meth) acrylate), neopentyl glycol two (methyl) acrylate (neopentylglycol di (meth) acrylate), pentaerythrite two (methyl) acrylate (pentaerythritol di (meth) acrylate), pentaerythrite three (methyl) acrylate (pentaerythritol tri (meth) acrylate), pentaerythrite four (methyl) acrylate (pentaerythritol tetra (meth) acrylate), pentaerythrite five (methyl) acrylate (pentaerythritol penta (meth) acrylate), pentaerythrite six (methyl) acrylate (pentaerythritol hexa (meth) acrylate), dipentaerythritol two (methyl) acrylate (dipentaerythritol di (meth) acrylate), dipentaerythritol three (methyl) acrylate (dipentaerythritol tri (meth) acrylate), dipentaerythritol four (methyl) acrylate (dipentaerythritol tetra (meth) acrylate), dipentaerythritol five (methyl) acrylate (dipentaerythritol penta (meth) acrylate), dipentaerythritol six (methyl) acrylate (dipentaerythritol hexa (meth) acrylate), bisphenol-A two (methyl) acrylate (bisphenol A di (meth) acrylate), trimethylolpropane tris (methyl) acrylate (trimethylolpropane tri (meth) acrylate), phenolic aldehyde epoxy (methyl) acrylate (novolac epoxy (meth) acrylate), there is dipentaerythritol five (methyl) acrylate (dipentaerythritol penta (meth) acrylate) derivant of carboxyl, oxirane glycerine trimethylolpropane tris (methyl) acrylate (ethyleneoxide glycerin trimethylopropane tri (meth) acrylate), and at least one compound in epoxypropane glycerine three (methyl) acrylate (propyleneoxide glycerin tri (meth) acrylate).
In addition, described heat polymerization or photopolymerization reaction oligomer can be at least one oligomer being selected from epoxy (methyl) acrylate oligomer (epoxy (meth) acrylate oligomer), amido formate (methyl) acrylate oligomer (urethane (meth) acrylate oligomer), sulfydryl (methyl) acrylate oligomer (thiol (meth) acrylate oligomer) and polyester (methyl) acrylate oligomer (polyester (meth) acrylate oligomer).
Taking the described binder resin of 100 weight portions as base Huaihe River, the content of described reactive unsaturated compound can be 100 to 250 weight portions, is preferably 150 to 250 weight portions, more preferably 100 to 200 weight portions.Particularly, in order to improve the problem that is difficult to realize pattern due to the low degree of cure (curing degree) due to photoresist, with respect to the described binder resin of 100 weight portions, preferably, the content of described reactive unsaturated compound is equal to or higher than 100 weight portions.In addition, if the addition of described reactive unsaturated compound is too much, the degree of cure of described photosensitive polymer combination can excessively increase, to such an extent as in the time developing the tearing phenomenon and can become seriously of pattern, and the flatness of pattern can reduce.In order to improve this problem, with respect to the described binder resin of 100 weight portions, preferably, the content of described reactive unsaturated compound is equal to or less than 250 weight portions.
Pigment
Photosensitive polymer combination according to the present invention comprises pigment.
Described pigment can be normal blueness or the viridine green using of the colored resin composition for colored filter being selected from the technology of the present invention field.
Described blue pigment can be taking copper phthalocyanine (copper phthalocyanine) as basic blue pigment, preferred compound is classified with the color index (color index) of pigment, and comprises color index alizarol saphirol (Color Index (C.I.) Pigment Blue) 15,15:3,15:4,15:6, the blue pigments such as 60.
Described viridine green can be taking halogenated phthalocyanines (halogenated phthalocyanine) as basic viridine green, preferred compound is classified with the color index (color index) of pigment, and comprises the viridine greens such as color index naphthol green (Color Index (C.I.) Pigment Green) 7,36,58.
Described pigment can directly itself add in photosensitive polymer combination of the present invention with its pigment, or adds in photosensitive polymer combination of the present invention to include the forms such as the dispersible pigment dispersion of spreading agent or solvent.
As the spreading agent that can be included in described dispersible pigment dispersion, optionally use non-ionic dispersing agent, ionic dispersant or cationic dispersing agent, its specific embodiment can comprise polyolefin diols (polyalkyleneglycol) and ester thereof; Polyoxyethylene (polyoxyalkylene); Polyol ester alkylene oxide addition product (multivalent alcohol ester alkylene oxide adduct); Alcohol alkylene oxide addition product (alcohol alkylene oxide adduct); Alkyl amine (alkylamine) and composition thereof.And with respect to the pigment of 100 weight portions, the content of described spreading agent can be 10 to 20 weight portions.
As the solvent that can be included in this dispersible pigment dispersion, can use glycol acetate (ethyleneglycol acetate), ethyl cellosolve (ethyl cellosolve), 1-Methoxy-2-propyl acetate (propyleneglycol methylether acetate), ethyl lactate (ethyl lactate), polyglycol (polyethyleneglycol), cyclohexanone (cyclohexanone), propylene glycol monomethyl ether (propyleneglycol methylether) etc.Preferably, the content control of described solvent is that to make the solid content of described dispersible pigment dispersion be 5 to 30wt%.
Meanwhile, the particle diameter of described pigment is considered dispersion stabilization and pixel resolution etc. and is determined, and the quantity mean grain size of described pigment (number average particle diameter) can be 30 to 200nm.
Taking the described binder resin of 100 weight portions as benchmark, the content of described pigment can be 50 to 150 weight portions, is preferably 75 to 150 weight portions, more preferably 75 to 125 weight portions.Particularly, consider the colour gamut (color gamut), pattern-forming (pattern formability), adhesion (adhesion), curability (curing property) etc. that use pigment, the content of described pigment is preferably in above-mentioned scope.
Dyestuff
Photosensitive polymer combination according to the present invention comprises dyestuff.
In other words, photosensitive polymer combination of the present invention comprises dyestuff (auxiliary dyestuff (auxiliary dye)) and above-mentioned pigment (main pigment).According to the present invention, described dyestuff has unique spectral characteristic in specific wavelength coverage, and by controlling transmittance and the light breadth of penetration (light transmission width) of the colored filter being formed by described photosensitive polymer combination with the synergy (synergistic action) of pigment that represents particular color, use and improve colour purity, brightness and contrast etc.
According to one embodiment of the invention, if described pigment is blue pigment, the dyestuff being represented by described Chemical formula 1 can be to have at 430 to 465nm wavelength coverage transmittances and is equal to or higher than 90%, be preferably 90 to 99%, more preferably 93 to 99%, and be equal to or less than 55% at 495 to 505nm wavelength coverage transmittances, be preferably 45 to 55%, more preferably the compound of 45 to 50% spectral characteristic.
According to another embodiment of the present invention, if described pigment is viridine green, the dyestuff being represented by described Chemical formula 1 can be to have at 530 to 540nm wavelength coverage transmittances and is equal to or higher than 95%, be preferably 95 to 99%, and be equal to or less than 55% at 580 to 590nm wavelength coverage transmittances, be preferably 45 to 55%, more preferably the compound of 45 to 50% spectral characteristic.
The dyestuff with above-mentioned spectral characteristic can be the compound being represented by following Chemical formula 1:
[Chemical formula 1]
In described Chemical formula 1,
M is copper, cobalt, aluminium, zinc, nickel, platinum or chromium;
N is nitrogen;
R 1to R 16be hydrogen atom, halogen atom, carboxyl, hydroxyl, sulfonic group, the sulfonic alkyl being replaced by a heterocyclic radical, sulfonic acid hydroxyl, sulfonic acid alkoxy, sulfonic acid aryl, the alkyl of carbon number 1 to 20, the naphthenic base of carbon number 3 to 20, the aryl of carbon number 6 to 20, assorted alkyl, the Heterocyclylalkyl of carbon number 3 to 20 or the heteroaryl of carbon number 3 to 20 of carbon number 1 to 20 independently of one another.
Preferably, the dyestuff that has an above-mentioned spectral characteristic can be the compound that represented by following Chemical formula 2:
[Chemical formula 2]
Figure BDA0000489795300000131
In described Chemical formula 2,
M is copper, cobalt, aluminium, zinc, nickel, platinum or chromium;
N is nitrogen;
O is oxygen;
R ato R hbe the alkyl of carbon number 1 to 20, the naphthenic base of carbon number 3 to 20, the aryl of carbon number 6 to 20, assorted alkyl, the Heterocyclylalkyl of carbon number 3 to 20 or the heteroaryl of carbon number 3 to 20 of carbon number 1 to 20 independently of one another.
The compound being represented by described Chemical formula 1 or Chemical formula 2 can be according to R 1to R 16or R ato R hstructure and substituent length and phase strange land shows blueness or green.
According to one embodiment of the invention, the blue dyes that meets above-mentioned spectral characteristic can be and is selected from eight (2-ethyl hexyl oxy) copper phthalocyanine (Octa (2-ethylhexyloxy) Cu Phthalocyanine), eight (2-ethyl hexyl oxy) cobalt phthalocyanine (Octa (2-ethylhexyloxy) Co Phthalocyanine), eight (2-ethyl hexyl oxy) aluminium phthalocyanine (Octa (2-ethylhexyloxy) Al Phthalocyanine), eight (2-ethyl hexyl oxy) ZnPc (Octa (2-ethylhexyloxy) Zn Phthalocyanine), eight (2-ethyl hexyl oxy) nickel phthalocyanine (Octa (2-ethylhexyloxy) Ni Phthalocyanine), eight (2-ethyl hexyl oxy) platinum phthalocyanine (Octa (2-ethylhexyloxy) Pt Phthalocyanine), and at least one compound in eight (2-ethyl hexyl oxy) chromium phthalocyanine (Octa (2-ethylhexyloxy) Cr Phthalocyanine), but be not limited to this.
In addition, according to one embodiment of the invention, the green colouring material that meets above-mentioned spectral characteristic can be and is selected from eight (1, 4, 7, 10-tetra-oxa-undecyls) copper phthalocyanine (Octa (1, 4, 7, 10-tetraoxaundecyl) Cu Phthalocyanine), eight (1, 4, 7, 10-tetra-oxa-undecyls) cobalt phthalocyanine (Octa (1, 4, 7, 10-tetraoxaundecyl) Co Phthalocyanine), eight (1, 4, 7, 10-tetra-oxa-undecyls) aluminium phthalocyanine (Octa (1, 4, 7, 10-tetraoxaundecyl) Al Phthalocyanine), eight (1, 4, 7, 10-tetra-oxa-undecyls) ZnPc (Octa (1, 4, 7, 10-tetraoxaundecyl) Zn Phthalocyanine), eight (1, 4, 7, 10-tetra-oxa-undecyls) nickel phthalocyanine (Octa (1, 4, 7, 10-tetraoxaundecyl) Ni Phthalocyanine), eight (1, 4, 7, 10-tetra-oxa-undecyls) platinum phthalocyanine (Octa (1, 4, 7, 10-tetraoxaundecyl) Pt Phthalocyanine), and eight (1, 4, 7, 10-tetra-oxa-undecyls) chromium phthalocyanine (Octa (1, 4, 7, 10-tetraoxaundecyl) Cr Phthalocyanine) at least one compound, but be not limited to this.
Taking the described binder resin of 100 weight portions as benchmark, the content of described dyestuff can be 50 to 250 weight portions, is preferably 100 to 250 weight portions, more preferably 100 to 200 weight portions.Particularly, promote effect in order to represent the MIN spectral characteristic of adding dyestuff and produce, taking the described binder resin of 100 weight portions as benchmark, the content of described dyestuff is preferably equal to or higher than 50 weight portions.And excessive if described dyestuff uses, after baking, dyestuff may be separated out or thermotolerance may reduce, in order to improve this problem, taking the described binder resin of 100 weight portions as benchmark, the content of described dyestuff is preferably 200 weight portions.
Polymerization initiator
Photosensitive polymer combination for colored filter according to the present invention comprises polymerization initiator.Described polymerization initiator can be activated by heat or light etc., thereby causes the polyreaction of above-mentioned reactive unsaturated compound, and described polymerization initiator can be used the normal in the art polymerization initiator using.
According to one embodiment of the invention, described polymerization initiator can be selected from the potpourri of acetophenone based compound (acetophenone-based compound), benzophenone based compound (benzophenone-based compound), thioxanthones based compound (thioxanthone-based compound), diphenylhydroxyethanone based compound (benzoin-based compound), triazine-based compound (triazine-based compound), oximido compound (oxime-based compound) and these compounds.
Particularly, described polymerization initiator can be and comprises 2, 2 '-diethoxy acetophenone (2, 2 '-diethoxyacetophenone), 2, 2 '-dibutoxy acetophenone (2, 2 '-dibutoxyacetophenone), (2-hydroxy-2-methyl ethyl) phenyl ketone ((2-hydroxy-2-methylethyl) phenylketone), p-three grades of butyl trichloroacetophenones (p-t-butyltrichloroacetophenone), p-three grades of butyl dichloroacetophenones (p-t-butyldichloroacetophenone), 4-chloro-acetophenone (4-chloroacetophenone), 2, 2 '-bis-chloro-4-metaphenoxy acetophenones (2, 2 '-dichloro-4-phenoxyacetophenone), 2-methyl isophthalic acid-(4-(methyl mercapto) phenyl) the acetophenone based compound of-2-Lin Ji-1-acetone (2-methyl-1-(4-(methylthio) phenyl)-2-morpholinopropan-1-one) etc., comprise benzophenone (benzophenone), benzoylbenzoic acid (benzoylbenzoic acid), phenacyl benzoic acid (benzoyl methylbenzoic acid), 4-phenyl benzophenone (4-phenyl benzophenone), dihydroxy benaophenonel (hydroxy benzophenone), acroleic acid esterification benzophenone (acrylated benzophenone), 4, 4 '-bis-(dimethyl amido) benzophenone (4, 4 '-bis (dimethyl amino) benzophenone), 4, 4 '-bis-(diethyl amido) benzophenone (4, 4 '-bis (diethyl amino) benzophenone), 4, 4 '-dichloro benzophenone (4, 4 '-dichlorobenzophenone), 3, 3 '-dimethyl-2-methoxy benzophenone (3, 3 '-dimethyl-2-methoxybenzophenone) etc. benzophenone based compound, comprise thioxanthones (thioxanthone), CTX (2-chlorothioxanthone), 2-methyl thioxanthones (2-methylthioxanthone), isopropyl thioxanthone (isopropyl thioxanthone), 2,4-diethyl thioxanthone (2,4-diethyl thioxanthone), 2, the thioxanthones based compound of 4-diisopropyl thioxanthones (2,4-diisopropyl thioxanthone), CTX (2-chloro thioxanthone) etc., comprise the diphenylhydroxyethanone based compound of diphenylhydroxyethanone (benzoin), diphenylhydroxyethanone methyl ether (benzoin methyl ether), diphenylhydroxyethanone ether (benzoin ethyl ether), diphenylhydroxyethanone isopropyl ether (benzoin isopropyl ether), diphenylhydroxyethanone isobutyl ether (benzoin isobutyl ether), benzyl dimethyl ketal (benzyldimethylketal) etc., comprise 2, 4, the chloro-s-triazine (2 of 6-tri-, 4, 6-trichloro-s-triazine), 2-phenyl-4, two (the trichloromethyl)-s-triazine (2-phenyl-4 of 6-, 6-bis (trichloro methyl)-s-triazine), 2-(3 ', 4 '-dimethoxy-styryl)-4, two (the trichloromethyl)-s-triazine (2-(3 ' of 6-, 4 '-dimethoxy styryl)-4, 6-bis (trichloro methyl)-s-triazine), 2-(4 '-methoxyl naphthyl)-4, two (the trichloromethyl)-s-triazine (2-(4 '-methoxy naphthyl)-4 of 6-, 6-bis (trichloromethyl)-s-triazine), the p-methoxyphenyl of 2-()-4, two (the trichloromethyl)-s-triazine (2-(p-methoxy phenyl)-4 of 6-, 6-bis (trichloro methyl)-s-triazine), the p-tolyl of 2-()-4, two (the trichloromethyl)-s-triazine (2-(p-tolyl)-4 of 6-, 6-bis (trichloromethyl)-s-triazine), 2-diphenyl-4, two (the trichloromethyl)-s-triazine (2-dipenyl-4 of 6-, 6-bis (trichloro methyl)-s-triazine), two (trichloromethyl)-6-styryl-s-triazines (bis (trichloro methyl)-6-styryl-s-triazine), 2-(naphthols-1-yl)-4, two (the trichloromethyl)-s-triazine (2-(naphtho 1-yl)-4 of 6-, 6-bis (trichloro methyl)-s-triazine), 2-(4-methoxynaphthol-1-yl)-4, two (the trichloromethyl)-s-triazine (2-(4-methoxy naphtho 1-yl)-4 of 6-, 6-bis (trichloromethyl)-s-triazine), 2, 4-trichloromethyl (piperonyl)-6-triazine (2, 4-trichloro methyl (piperonyl)-6-triazine), 2, 4-trichloromethyl (4 '-methoxyl-styrene)-6-triazine (2, 4-trichloro methyl (4 '-methoxy styryl)-6-triazine) etc. triazine-based compound, comprise 1,2-octane diketone-1-(4-phenyl sulfo-) the o-benzoyl oximes of phenyl-2-() (1,2-octanedione-1-(4-phenylthio) phenol-2-(o-benzoyloxime) and ethyl ketone-1-(9-ethyl)-6-(2-methyl benzoyl-3-yl)-1-(o-acetyl-base oxime) oximido compound of (ethanone-1-(9-ethyl)-6-(2-methylbenzoyl-3-yl)-1-(o-acetyloxime)) etc., or the potpourri of these compounds.
In addition, can use click to sit the compounds such as based compound (carbazole-based compound), diketo compound (diketone compound), boric acid sulfonium based compound (sulfonium borate-based compound), diazo compound (diazo-based compound), two miaows seat based compounds (biimidazole-based compound) as described polymerization initiator.
Consider the problem reducing because of transmittance that after polyreaction, unreacted initiator causes, the content of described polymerization initiator is determined with abundant initiated polymerization.According to the present invention, taking the described binder resin of 100 weight portions as benchmark, the content of described polymerization initiator can be 5 to 50 weight portions, is preferably 10 to 50 weight portions, more preferably 10 to 40 weight portions.
Solvent
Photosensitive polymer combination for colored filter according to the present invention comprises solvent.
Described solvent adds for solubleness and the stickiness of controlling composition contained in described composition etc., as long as described solvent does not react with mentioned component and has compatibility with mentioned component, just be not particularly limited, can use the normal in the art solvent using.
According to one embodiment of the invention, described solvent can be the alcohols such as methyl alcohol (methanol), ethanol (ethanol), isopropyl alcohol (isopropylalcohol), butanols (butylalcohol), phenmethylol (benzylalcohol), diacetone alcohol (diacetonealcohol) etc., such as the ethers of dichloroethyl ether (dichloroethylether), n-butyl ether (n-butylether), isoamyl ether (diisoamylether), methyl phenyl ether (methylphenylether), tetrahydrofuran (tetrahydrofurane) etc., such as glycol ether (glycol ether) class of glycol monoethyl ether (ethyleneglycol monomethylether), ethylene glycol monoethyl ether (ethylene glycol monoethylether) etc., such as cellosolve acetic acid esters (cellosolve acetate) class of methylcellosolve acetate (methyl cellosolve acetate), ethyl cellosolve acetate (ethyl cellosolve acetate), ethylene glycol diethyl ether acetic acid esters (diethyl cellosolve acetate) etc., such as Methylethyl carbitol (methylethyl carbitol), diethyl carbitol (diethyl carbitol), diethylene glycol monomethyl ether (diethylene glycol monomethylether), diethylene glycol monoethyl ether (diethylene glycol monoethylether), diethylene glycol dimethyl ether (diethylene glycol dimethylether), diethylene glycol ethylmethyl ether (diethylene glycol methylethylether), carbitol (carbitol) class of diethylene glycol diethyl ether (diethylene glycol diethylether) etc., such as alkyl ether acetate (alkylether acetates) class of propylene glycol Methylethyl acetate (propyleneglycol methylethyl acetate), 1-Methoxy-2-propyl acetate (propyleneglycol methylether acetate), propylene glycol propyl ether acetate (propyleneglycol propylether acetate) etc., such as aromatic hydrocarbon (aromatic hydrocarbons) class of toluene (toluene), dimethylbenzene (xylene) etc., such as methyl ethyl ketone (methylethylketone), cyclohexanone (cyclohexanone), 4-hydroxy-4-methyl-2-pentanone, (4-hydroxy-4-methyl-2-pentanone), methyl-n-propyl ketone (methyl-n-propylketone), methyl-normal-butyl ketone (methyl-n-butylketone), methyl-n-amyl ketone (methyl-n-amylketone), ketone (ketones) class of 2-HEPTANONE (2-heptanone) etc., such as representative examples of saturated aliphatic monocarboxylic acid Arrcostab (the saturated aliphatic monocarboxylic acid alkyl esters) class of ethyl acetate (acetic acid ethyl), n-butyl acetate (acetic acid-n-butyl), isobutyl acetate (acetic acid isobutyl) etc., such as lactate (the lactic acid ester) class of methyl lactate (lactic acid methyl), ethyl lactate (lactic acid ethyl) etc., such as fluoroacetic acid Arrcostab (the oxy acetic acid alkyl ester) class of fluoroacetic acid methyl esters (oxy acetic acid methyl), fluoroacetic acid ethyl ester (oxy acetic acid ethyl), fluoroacetic acid butyl ester (oxy acetic acid butyl) etc., such as alcoxyl alkyl acetate (the alkoxy acetic acid alkyl ester) class of methoxyimino acetic acid methyl esters (methoxy acetic acid methyl), methoxyimino acetic acid ethyl ester (methoxy acetic acid ethyl), methoxyimino acetic acid butyl ester (mexhoty acetic acid butyl), ethoxy methyl acetate (ethoxy acetic acid methyl), ethoxy ethyl acetate (ethoxy acetic acid ethyl) etc., such as 3-oxygen alkyl propionates (the 3-oxy propionic acid alkyl ester) class of 3-oxygen methyl propionate (3-oxy propionic acid methyl), 3-oxygen ethyl propionate (3-oxy propionic acid ethyl) etc., such as 3-alkoxy propionic acid Arrcostab (the 3-alkoxy propionic acid alkyl ester) class of 3-methoxy methyl propionate (3-methoxy propionic acid methyl), 3-methoxy ethyl propionate (3-methoxy propionic acid ethyl), 3-ethoxy ethyl propionate (3-ethoxy propionic acid ethyl), 3-ethoxy methyl propionate (3-ethoxy propionic acid methyl) etc., such as 2-oxygen alkyl propionates (the 2-oxy propionic acid alkyl ester) class of 2-oxygen methyl propionate (2-oxy propionic acid methyl), 2-oxygen ethyl propionate (2-oxy propionic acid ethyl), 2-oxygen propyl propionate (2-oxy propionic acid propyl) etc., such as 2-alkoxy propionic acid Arrcostab (the 2-alkoxy propionic acid alkyl ester) class of 2-methoxy methyl propionate (2-methoxy propionic acid methyl), 2-methoxy ethyl propionate (2-methoxy propionic acid ethyl), 2-ethoxy ethyl propionate (2-ethoxy propionic acid ethyl), 2-ethoxy methyl propionate (2-ethoxy propionic acid methyl) etc., such as 2-oxygen-2 Methylpropionic acid ester (2-oxy-2-methyl propionic acid ester) class of 2-oxygen-2 Methylpropionic acid methyl esters (2-oxy-2-methyl propionic acid methyl), 2-oxygen-2 Methylpropionic acid ethyl ester (2-oxy-2-methyl propionic acid ethyl) etc., such as single oxygen monocarboxylic acid Arrcostab (monooxy monocarboxylic acid alkyl ester of2-alkoxy-2-methyl propionic acid alkyl) class of 2-alkoxy-2 Methylpropionic acid alkyl of 2-methoxy-2 Methylpropionic acid methyl esters (2-methoxy-2-methyl propionic acid methyl), 2-ethoxy-2 Methylpropionic acid ethyl ester (2-ethoxy-2-methyl propionic acid ethyl) etc., such as ester (ester) class of 2 hydroxy propanoic acid ethyl ester (2-hydroxy propionic acid ethyl), 2-hydroxy-2-methyl ethyl propionate (2-hydroxy-2-methyl propionic acid ethyl), hydroxyl ethyl acetate (hydroxyl acetic acid ethyl), 2-hydroxy-3-methyl methyl butyrate (2-hydroxy-3-methyl butyric acid methyl) etc., such as keto ester (the ketonic acid ester) class of ethyl pyruvate (pyruvic acid ethyl) etc., or the potpourri of these compounds.
In addition, described solvent can comprise N-METHYLFORMAMIDE (N-methylformamide), DMF (N, N-dimethylformamide), N-methyl formyl aniline (N-methylformanilide), N-methylacetamide (N-methylacetamide), DMA (N, N-dimethylacetamide), N-N-methyl 2-pyrrolidone N-(N-methylpyrrolidone), dimethyl sulfoxide (DMSO) (dimethylsulfoxide), benzyl ether (benzylethylether), hexyl ether (dihexylether), diacetone (acetylacetone), isophorone (isophorone), caproic acid (caproic acid), sad (caprylic acid), 1-octanol (1-octanol), 1 nonyl alcohol (1-nonanol), benzylated polyol (benzylalcohol), benzyl acetate (acetic acid benzyl), ethyl benzoate (benzoic acid ethyl), diethy-aceto oxalate (oxalic acid diethyl), diethyl maleate (maleic acid diethyl), gamma-butyrolacton (gamma-butyrolactone), ethyl carbonate (ethylene carbonate), propyl carbonate (propylene carbonate), ethylene glycol monophenyl ether acetate (phenyl cellosolve acetate), glycol acetate (ethyleneglycol acetate), ethyl cellosolve (ethyl cellosolve), ethyl lactate (ethyl lactate), polyglycol (polyethyleneglycol) etc.
Consider compatibility and reactivity, preferably, use glycol ether (glycol ether) class such as ethylene glycol monoethyl ether (ethylene glycol monoethyl ether) etc. as described solvent; Such as cellosolve acetic acid esters (cellosolve acetate) class of (ethyl cellosolve acetate) etc.; Such as ester (ester) class of 2 hydroxy propanoic acid ethyl ester (2-hydroxy propionic acid ethyl) etc.; Such as carbitol (carbitol) class of diethylene glycol monomethyl ether (diethyleneglycol monomethyl ether); Such as propylene glycol alkyl ether acetate (the propylene glycol alkylether acetate) class of 1-Methoxy-2-propyl acetate (propyleneglycol methylether acetate), propylene glycol propyl ether acetate (propylene glycol propyl ether acetate) etc.; The potpourri of glycol acetate (ethyleneglycol acetate), ethyl cellosolve (ethyl cellosolve), ethyl lactate (ethyl lactate), polyglycol (polyethyleneglycol) or these compounds.
The content of described solvent is considered volatility of stickiness, coating and this solvent of described photosensitive polymer combination etc. and is determined.According to the present invention, taking the described binder resin of 100 weight portions as benchmark, the content of described solvent can be 100 to 500 weight portions, is preferably 150 to 450 weight portions, more preferably 200 to 400 weight portions.
Other additives
Can further comprise other conventional in the art additives according to the photosensitive polymer combination for colored filter of the present invention.
These additives can be the compositions of storage stability or coating and adhesion etc. for improving photosensitive polymer combination.According to the present invention, described additive can be epoxy compound (epoxy compound), malonic acid (malonic acid), 3-amido-1,2-propylene glycol (3-amino-1,2-propandiol), silylation (silane based) coupling agent, silica-based or fluorine-containing smoothing agent, interfacial agent etc.In addition, the content of described additive decides according to the physical property that will control, is not particularly limited, as long as the physical property of photosensitive polymer combination is not had to adverse effect.
Meanwhile, according to another object of the present invention, provide a kind of colored filter that uses above-mentioned photosensitive polymer combination to make.
Described colored filter except use photosensitive polymer combination of the present invention, can utilize in the art the mode of normal use to manufacture.
According to one embodiment of the invention, described colored filter can be by rotary coating (spin coating) or slot coated (slit coating), described photosensitive polymer combination is coated with to 1 to 5 μ m to a substrate, irradiation is to form pattern, manufactured with developer processing afterwards, and if necessary, can carry out baking process (baking process) to form required pattern.
Below, preferred embodiment is described to help to understand the present invention.But following examples are only in order to illustrate the present invention, scope of the present invention is not as limit.
[Preparation Example]
Preparation Example 1
(preparation of binder)
Comprise 33wt% methacrylic acid (methacrylic acid) with respect to 100 weight portions, 40wt% benzyl methacrylate (benzylmethacrylate), 11wt% ethyl triethylene glycol methacrylate (ethyltriglycol methacrylate), and the monomeric compound of 16wt% HEMA (2-hydroxyethylmethacrylate), mix the polymerization initiator (azoisobutyronitrile of 4 weight portions, and the solvent (dihydroxypropane single-ether of 55 weight portions azobisisobutyronitrile), propyleneglycol monoethylether), and carry out polymerization taking preparation weight-average molecular weight as 30, 000 fluoropolymer resin.
Preparation Example 2-1
(synthesizing of blue dyes: eight (2-ethyl hexyl oxy) copper phthalocyanine)
By approximately 12.8 grams 1,2-bis-(2-ethyl hexyl oxy)-4, the smelly benzene (1 of 5-bis-, 2-Di (2-ethylhexyloxy)-4,5-dibromobenzene) and the copper cyanider of approximately 7.0 grams (Copper cyanide) be added in solvent dimethyl formamide (Dimethylformamide) (about 130mL), aforementioned potpourri at room temperature stirs 5 hours in nitrogen environment.Afterwards, reduce pressure and obtain 1 to remove solvent, 2-bis-(2-ethyl hexyl oxy)-4, the smelly benzene of 5-bis-(1,2-Di (2-ethylhexyloxy)-4,5-dibromobenzene).
Then, by 1,2-bis-(2-ethyl hexyl oxy)-4, the smelly benzene of 5-bis-(approximately 2 grams), ammonia (approximately 2 grams) and sodium (approximately 0.34 gram) are added in solvent methanol (about 34mL), aforementioned potpourri at room temperature stir about 5 hours to obtain 1,3-di-imidogen-5, the different diindyl (1 that draws of 6-bis-(2-ethyl hexyl oxy), 3-Diimino-5,6-di (2-ethylhexyloxy) isoindole).
Mix 1,3-di-imidogen-5, different diindyl (approximately 1.19 grams) and the copper (approximately 0.2 gram) of drawing of 6-bis-(2-ethyl hexyl oxy) reacts approximately 96 hours to obtain eight (2-ethyl hexyl oxy) copper phthalocyanine at approximately 270 DEG C of temperature.
Preparation Example 2-2
(synthesizing of blue dyes: eight (2-ethyl hexyl oxy) cobalt phthalocyanine)
By approximately 12.8 grams 1,2-bis-(2-ethyl hexyl oxy)-4, the copper cyanider (Copper cyanide) of the smelly benzene of 5-bis-and approximately 7.0 grams is added in solvent dimethyl formamide (Dimethylformamide) (about 130mL), and aforementioned potpourri at room temperature stirs 5 hours in nitrogen environment.Afterwards, reduce pressure and obtain 1 to remove solvent, 2-bis-(2-ethyl hexyl oxy)-4, the smelly benzene of 5-bis-(1,2-Di (2-ethylhexyloxy)-4,5-dibromobenzene).
Then, by 1,2-bis-(2-ethyl hexyl oxy)-4, the smelly benzene of 5-bis-(approximately 2 grams), ammonia (approximately 2 grams) and sodium (approximately 0.34 gram) are added in solvent methanol (about 34mL), aforementioned potpourri at room temperature stir about 5 hours to obtain 1,3-di-imidogen-5, the different diindyl that draws of 6-bis-(2-ethyl hexyl oxy).
Mix 1,3-di-imidogen-5, different diindyl (approximately 2 grams) and the p-dihydroxy-benzene (approximately 0.215 gram) of drawing of 6-bis-(2-ethyl hexyl oxy) reacts approximately 48 hours to obtain eight (2-ethyl hexyl oxy) dihydro phthalocyanine (Octa (2-ethylhexyloxy) Dihydrogen Phthalocyanine) at approximately 210 DEG C of temperature.
Afterwards, mix eight (2-ethyl hexyl oxy) dihydro phthalocyanine (approximately 1.0 grams) and cobaltous dichloride (approximately 0.363 gram), at room temperature react approximately 24 hours to obtain eight (2-ethyl hexyl oxy) cobalt phthalocyanine.
Preparation Example 2-3
(synthesizing of blue dyes: eight (2-ethyl hexyl oxy) platinum phthalocyanine)
By approximately 12.8 grams 1,2-bis-(2-ethyl hexyl oxy)-4, the copper cyanider (Copper cyanide) of the smelly benzene of 5-bis-and approximately 7.0 grams is added in solvent dimethyl formamide (Dimethylformamide) (about 130mL), and aforementioned potpourri stirs 5 hours in nitrogen environment under room temperature.Afterwards, reduce pressure and obtain 1 to remove solvent, 2-bis-(2-ethyl hexyl oxy)-4, the smelly benzene of 5-bis-(1,2-Di (2-ethylhexyloxy)-4,5-dibromobenzene).
Then, by 1,2-bis-(2-ethyl hexyl oxy)-4, the smelly benzene of 5-bis-(approximately 2 grams), ammonia (approximately 2 grams) and sodium (approximately 0.34 gram) are added in solvent methanol (about 34mL), aforementioned potpourri at room temperature stirs 5 hours to obtain 1,3-di-imidogen-5, the different diindyl that draws of 6-bis-(2-ethyl hexyl oxy).
Mix 1,3-di-imidogen-5, different diindyl (approximately 1.5 grams) and the platinous chloride (approximately 0.311 gram) of drawing of 6-bis-(2-ethyl hexyl oxy) reacts approximately 48 hours to obtain eight (2-ethyl hexyl oxy) platinum phthalocyanine at approximately 270 DEG C of temperature.
Preparation Example 2-4
(synthesizing of blue dyes: eight (2-ethyl hexyl oxy) dihydro phthalocyanine)
By approximately 12.8 grams 1,2-bis-(2-ethyl hexyl oxy)-4, the copper cyanider (Copper cyanide) of the smelly benzene of 5-bis-and approximately 7.0 grams is added in solvent dimethyl formamide (Dimethylformamide) (about 130mL), aforementioned potpourri stir about 5 hours at room temperature in nitrogen environment.Afterwards, reduce pressure and obtain 1 to remove solvent, 2-bis-(2-ethyl hexyl oxy)-4, the smelly benzene of 5-bis-(1,2-Di (2-ethylhexyloxy)-4,5-dibromobenzene).
Then, by 1,2-bis-(2-ethyl hexyl oxy)-4, the smelly benzene of 5-bis-(approximately 2 grams), ammonia (approximately 2 grams) and sodium (approximately 0.34 gram) are added in solvent methanol (about 34mL), aforementioned potpourri at room temperature stir about 5 hours to obtain 1,3-di-imidogen-5, the different diindyl that draws of 6-bis-(2-ethyl hexyl oxy).
Mix 1,3-di-imidogen-5, different diindyl (approximately 2 grams) and the p-dihydroxy-benzene (approximately 0.215 gram) of drawing of 6-bis-(2-ethyl hexyl oxy), aforementioned potpourri reacts approximately 48 hours to obtain eight (2-ethyl hexyl oxy) dihydro phthalocyanine (Octa (2-ethylhexyloxy) Dihydrogen Phthalocyanine) at approximately 210 DEG C of temperature.
Preparation Example 3-1
(synthesizing of green colouring material: eight (Isosorbide-5-Nitrae, 7,10-, tetra-oxa-undecyls) copper phthalocyanine)
By approximately 12.6 grams 1,2-bis-(2-ethyl hexyl oxy)-4, the copper cyanider (Copper cyanide) of the smelly benzene of 5-bis-and approximately 6.05 grams is added in solvent dimethyl formamide (Dimethylformamide) (about 114mL), aforementioned potpourri in nitrogen environment at 130 DEG C stir about 15 hours.Thereafter, thus reducing pressure obtains 1,2-bis-(Isosorbide-5-Nitrae, 7,10-, tetra-oxa-undecyls)-4,5-dicyanobenzenes (1,2-Di (Isosorbide-5-Nitrae, 7,10-tetraoxaundecyl)-4,5-dicyanobenzene) to remove solvent.
Then, by 1,2-bis-(1,4,7,10-, tetra-oxa-undecyls)-4,5-dicyanobenzenes (approximately 3.55 grams), ammonia (approximately 2.0 grams) and sodium (approximately 0.39 gram) are added in solvent methanol (about 39mL), aforementioned potpourri at room temperature stir about 5 hours to obtain 1,3-di-imidogen-5,6-bis-(Isosorbide-5-Nitrae, 7,10-tetra-oxa-undecyls) different diindyl (1,3-Diimino-5, the 6-di (1 of drawing, 4,7,10-tetraoxaundecyl) isoindole).
Mix 1,3-di-imidogen-5,6-bis-(1,4,7,10-, tetra-oxa-undecyls) different diindyl (approximately 1 gram) and the copper (approximately 0.140 gram) of drawing, aforementioned potpourri reacts approximately 18 hours to obtain eight (1 at approximately 220 DEG C of temperature, 4,7,10-, tetra-oxa-undecyls) copper phthalocyanine (Octa (Isosorbide-5-Nitrae, 7,10-tetraoxaundecyl) Cu Phthalocyanine).
Preparation Example 3-2
(synthesizing of green colouring material: eight (Isosorbide-5-Nitrae, 7,10-, tetra-oxa-undecyls) cobalt phthalocyanine)
By approximately 12.6 grams 1,2-bis-(2-ethyl hexyl oxy)-4, the copper cyanider (Copper cyanide) of the smelly benzene of 5-bis-and approximately 6.05 grams is added in solvent dimethyl formamide (Dimethylformamide) (about 114mL), aforementioned potpourri stir about 15 hours at 130 DEG C.Afterwards, thus reducing pressure obtains 1,2-bis-(Isosorbide-5-Nitrae, 7,10-, tetra-oxa-undecyls)-4,5-dicyanobenzenes (1,2-Di (Isosorbide-5-Nitrae, 7,10-tetraoxaundecyl)-4,5-dicyanobenzene) to remove solvent.
Then, by 1,2-bis-(1,4,7,10-, tetra-oxa-undecyls)-4,5-dicyanobenzenes (approximately 3.55 grams), ammonia (approximately 2.0 grams) and sodium (approximately 0.39 gram) are added in solvent methanol (about 39mL), aforementioned potpourri at room temperature stir about 5 hours to obtain 1,3-di-imidogen-5,6-bis-(Isosorbide-5-Nitrae, 7,10-tetra-oxa-undecyls) different diindyl (1,3-Diimino-5, the 6-di (1 of drawing, 4,7,10-tetraoxaundecyl) isoindole).
Mix 1,3-di-imidogen-5,6-bis-(1,4,7,10-, tetra-oxa-undecyls) different diindyl (approximately 1.60 grams) and the cobalt (approximately 0.419 gram) of drawing, aforementioned potpourri reacts approximately 17 hours to obtain eight (1 at approximately 280 DEG C of temperature, 4,7,10-, tetra-oxa-undecyls) cobalt phthalocyanine (Octa (Isosorbide-5-Nitrae, 7,10-tetraoxaundecyl) Co Phthalocyanine).
Preparation Example 3-3
(synthesizing of green colouring material: eight (Isosorbide-5-Nitrae, 7,10-, tetra-oxa-undecyls) platinum phthalocyanine)
By approximately 12.6 grams 1,2-bis-(2-ethyl hexyl oxy)-4, the copper cyanider (Copper cyanide) of the smelly benzene of 5-bis-and approximately 6.05 grams is added in solvent dimethyl formamide (Dimethylformamide) (about 114mL), aforementioned potpourri stir about 15 hours at 130 DEG C.Afterwards, thus reducing pressure obtains 1,2-bis-(Isosorbide-5-Nitrae, 7,10-, tetra-oxa-undecyls)-4,5-dicyanobenzenes (1,2-Di (Isosorbide-5-Nitrae, 7,10-tetraoxaundecyl)-4,5-dicyanobenzene) to remove solvent.
Then, by 1,2-bis-(1,4,7,10-, tetra-oxa-undecyls)-4,5-dicyanobenzenes (approximately 3.55 grams), ammonia (approximately 2.0 grams) and sodium (approximately 0.39 gram) are added in solvent methanol (about 39mL), aforementioned potpourri at room temperature stir about 5 hours to obtain 1,3-di-imidogen-5,6-bis-(Isosorbide-5-Nitrae, 7,10-tetra-oxa-undecyls) different diindyl (1,3-Diimino-5, the 6-di (1 of drawing, 4,7,10-tetraoxaundecyl) isoindole).
By 1,3-di-imidogen-5,6-bis-(1,4,7,10-, tetra-oxa-undecyls) differently draw diindyl (approximately 1.5 grams) and platinous chloride (approximately 0.250 gram) is added in dimethyl formamide (about 3.0mL), aforementioned potpourri at room temperature reacts approximately 24 hours to obtain eight (1,4,7,10-, tetra-oxa-undecyls) platinum phthalocyanine (Octa (Isosorbide-5-Nitrae, 7,10-tetraoxaundecyl) Pt Phthalocyanine).
[embodiment and comparative example]
Embodiment 1
Taking the binder resin of the Preparation Example 1 of 100 weight portions as base Huaihe River;
Mix the reactive unsaturated compound (the bisphenol epoxies acrylate oligomer (bisphenol epoxy acrylate oligomer) of approximately 50 weight portions and the dipentaerythritol acrylate (dipentaerythritol hexaacrylate) of approximately 125 weight portions) of approximately 175 weight portions;
The blue pigment dispersion liquid of approximately 625 weight portions (name of product: DJBLUE-01, manufacturer: MIKYNI, solvent: 1-Methoxy-2-propyl acetate, the dispersion liquid that contains 15wt% pigment is approximately 93.75 weight portions in the time being converted to pigment content);
Polymerization initiator (the name of product OX-01 of approximately 6.25 weight portions of approximately 28.75 weight portions, manufacturer: BASF, the name of product Irgacure-369 of approximately 15 weight portions, manufacturer: BASF, and approximately 7.5 weight portions 4,4 '-bis-(dimethylamino) diphenylketone (4,4 '-bisdiethylaminobenzophenone));
The solvent 1-Methoxy-2-propyl acetate of approximately 316.25 weight portions; And
The fluorine-containing smoothing agent (name of product: F-474, manufacturer: DIC) of approximately 0.05 weight portion, and at room temperature stir about 2 hours of aforementioned potpourri, afterwards, uses the filtration unit removal of impurity of 1.2 μ m.
Taking the binder resin of 100 weight portions as base Huaihe River, the dyestuff of the Preparation Example 2-1 of approximately 125 weight portions is mixed with said mixture, and by gained potpourri at room temperature stir about 2 hours to prepare photosensitive polymer combination.
Embodiment 2
Prepare photosensitive polymer combination with the method identical with embodiment 1 and condition, but the dyestuff of Preparation Example 2-1 is replaced to the dyestuff of the Preparation Example 2-2 of identical addition.
Embodiment 3
Prepare photosensitive polymer combination with the method identical with embodiment 1 and condition, but the dyestuff of Preparation Example 2-1 is replaced to the dyestuff of Preparation Example 2-3, and taking the binder resin of 100 weight portions as base Huaihe River, the dyestuff addition of Preparation Example 2-3 is approximately 100 weight portions.
Comparative example 1
Prepare photosensitive polymer combination with the method identical with embodiment 1 and condition, but do not add the dyestuff of Preparation Example 2-1.
Comparative example 2
Prepare photosensitive polymer combination with the method identical with embodiment 1 and condition, but the dyestuff of Preparation Example 2-1 is replaced to the dyestuff of the Preparation Example 2-4 of identical addition.
Embodiment 4
Taking the binder resin of the Preparation Example 1 of 100 weight portions as base Huaihe River;
Mix the reactive unsaturated compound (the bisphenol epoxies acrylate oligomer (bisphenol epoxy acrylate oligomer) of approximately 50 weight portions and the dipentaerythritol acrylate (dipentaerythritol hexaacrylate) of approximately 125 weight portions) of approximately 175 weight portions;
The viridine green dispersion liquid of approximately 750 weight portions (name of product: DJGREEN-01, manufacturer: Special Pigment, solvent: 1-Methoxy-2-propyl acetate, the dispersion liquid that contains 15wt% pigment is approximately 112.5 weight portions in the time being converted to pigment content);
Polymerization initiator (the name of product OX-01 of approximately 6.25 weight portions of approximately 28.75 weight portions, manufacturer: BASF, the name of product Irgacure-369 of approximately 15 weight portions, manufacturer: BASF, and approximately 7.5 weight portions 4,4 '-bis-(dimethylamino) diphenylketone (4,4 '-bisdiethylaminobenzophenone));
The solvent 1-Methoxy-2-propyl acetate of approximately 316.25 weight portions; And
The fluorine-containing smoothing agent (name of product: F-474, manufacturer: DIC) of approximately 0.05 weight portion, and at room temperature stir about 2 hours of aforementioned potpourri, afterwards, uses the filtration unit removal of impurity of 1.2 μ m.
Taking the binder resin of 100 weight portions as base Huaihe River, the dyestuff of the Preparation Example 3-1 of approximately 187.5 weight portions is mixed with said mixture, and by gained potpourri at room temperature stir about 2 hours to prepare photosensitive polymer combination.
Embodiment 5
Prepare photosensitive polymer combination with the method identical with embodiment 4 and condition, but the dyestuff of Preparation Example 3-1 is replaced to the dyestuff of the Preparation Example 3-2 of identical addition.
Embodiment 6
Prepare photosensitive polymer combination with the method identical with embodiment 4 and condition, but the dyestuff of Preparation Example 3-1 is replaced to the dyestuff of Preparation Example 3-3, and taking the binder resin of 100 weight portions as base Huaihe River, the dyestuff addition of Preparation Example 3-3 is approximately 162.5 weight portions.
Comparative example 3
Prepare photosensitive polymer combination with the method identical with embodiment 4 and condition, but do not add the dyestuff of Preparation Example 3-1.
[experimental example]
Experimental example 1
(measuring the transmittance of pigment and dyestuff according to wavelength coverage)
Use colour measurement equipment (manufacturer: Otsuka, model: MCPD-3000) measure respectively in embodiment 1 to 3 blue pigment using spectral characteristic (Fig. 1 a), the spectral characteristic of the dyestuff of Preparation Example 2-1 (Fig. 1 b), the spectral characteristic of the viridine green that uses in embodiment 4 to 6 (Fig. 2 a) and the spectral characteristic of the dyestuff of Preparation Example 3-1 (Fig. 2 b), and be the results are shown in Fig. 1 and Fig. 2.
As shown in Figure 1 b, the dyestuff of its susceptible of proof Preparation Example 2-1 has in 430 to 465nm wavelength coverages the transmittance that is equal to or higher than 90%, and has in 495 to 505nm wavelength coverages the transmittance that is equal to or less than 55%.
In addition, as shown in Figure 2 b, the dyestuff of its susceptible of proof Preparation Example 3-1 has in 530 to 540nm wavelength coverages the transmittance that is equal to or higher than 95%, and has in 580 to 590nm wavelength coverages the transmittance that is equal to or less than 55%.
Experimental example 2
The photosensitive polymer combination of embodiment and comparative example is coated with to 2 μ m with method of spin coating respectively upper to glass substrate (10X10 centimetre), and on the heating plate of 90 DEG C prebake conditions 2 minutes, afterwards, at room temperature cooling 1 minute.Use exposure device with 100mJ/cm 2(365nm) after exposure is exposed, rear baking 30 minutes in the draft furnace of 220 DEG C.
Each sample of being manufactured by said method, measures its spectral characteristic, transmittance, brightness, contrast and thermotolerance in the following manner, and will the results are shown in table 1 to 2 and Fig. 3 to 5.
(colored filter is measured transmittance and is observed outward appearance according to wavelength coverage)
To the colored filter sample that uses the photosensitive polymer combination of embodiment 2 and comparative example 1 to make respectively and the colored filter sample that uses the photosensitive polymer combination of embodiment 5 and comparative example 3 to make respectively, use colour measurement equipment (manufacturer: Otsuka, model: MCPD-3000) and measure transmittance according to wavelength coverage, and result is shown in to Fig. 3 and Fig. 4.
In addition, the outward appearance of the colored filter that use embodiment 2 and embodiment 5 make is respectively exaggerated and observes, and it the results are shown in Fig. 5 a to 5b.
As shown in Figure 3 and 4, its susceptible of proof is owing to meeting the embodiment that has a dyestuff of unique spectrum characteristic in particular range of wavelengths and carry out the perparation of specimen with including, the transmittance of colored filter and light breadth of penetration are by being controlled with the synergy of pigment, thus raising colour purity.
(transmittance measurement)
Use MCPD-3000 equipment (manufacturer: Otsuka) to measure the transmittance (%) of rear baking substrate, wherein blue pigment is in 450 to 460nm wavelength coverage, to measure maximum transmission rate (Max%), and viridine green is in 515 to 550nm wavelength coverage, to measure maximum transmission rate (Max%).
(measurement of brightness)
The brightness (Y) that uses MCPD-3000 equipment (manufacturer: Otsuka) to measure rear baking substrate, wherein, carrys out comparison brightness taking particular color coordinate as benchmark, blue pigment is 0.14 in x, y 0.06 measures, and viridine green is that 0.25, y 0.63 measures in x.
(contrast measurement)
Use CT-1 equipment (manufacturer: TSUBOSAKA) to measure according to the contrast of polarization, wherein contrast is with the reference value 30 of naked state (Bare state), and 000:1 is measured.
(thermotolerance measurement)
The substrate of baking after heating in the baking box of 240 DEG C 30 minutes, measures thereafter aberration (Δ Eab).
[table 1]
Figure BDA0000489795300000281
[table 2]
Figure BDA0000489795300000282
As shown in table 1 and table 2, its susceptible of proof is compared with embodiment, the blueness and the green tint colo(u)r filter that use the photosensitive polymer combination of comparative example 1 and comparative example 3 to make have lower transmittance and brightness, and due to the particle scattering characteristic of pigment, and there is relatively low contrast.
In addition, although the blue color filter that uses the photosensitive polymer combination of comparative example 2 to make has similar transmittance, brightness and contrast compared with embodiment, but there is lower thermotolerance, be not therefore suitable for including the manufacturing process of heat treated liquid crystal indicator.
On the contrary, the colored filter sample that uses the photosensitive polymer combination of embodiment 1 to 6 to make all has excellent transmittance, brightness and contrast, and aspect thermotolerance, also meets actual use required 3 or lower reference value.

Claims (10)

1. for a photosensitive polymer combination for colored filter, comprise:
Binder resin;
Reactive unsaturated compound;
Blue pigment;
Dyestuff, it has in 430 to 465nm wavelength coverages the transmittance that is equal to or higher than 90%, and has in 495 to 505nm wavelength coverages the transmittance that is equal to or less than 55%;
Polymerization initiator; And
Solvent.
2. for a photosensitive polymer combination for colored filter, comprise:
Binder resin;
Reactive unsaturated compound;
Viridine green;
Dyestuff, it has in 530 to 540nm wavelength coverages the transmittance that is equal to or higher than 95%, and has in 580 to 590nm wavelength coverages the transmittance that is equal to or less than 55%;
Polymerization initiator; And
Solvent.
3. the photosensitive polymer combination for colored filter according to claim 1 and 2, wherein, described dyestuff is the compound being represented by following Chemical formula 1:
[Chemical formula 1]
Figure FDA0000489795290000021
In described Chemical formula 1,
M is copper, cobalt, aluminium, zinc, nickel, platinum or chromium;
N is nitrogen;
R 1to R 16be hydrogen atom, halogen atom, carboxyl, hydroxyl, sulfonic group, the sulfonic alkyl being replaced by a heterocyclic radical, sulfonic acid hydroxyl, sulfonic acid alkoxy, sulfonic acid aryl, the alkyl of carbon number 1 to 20, the naphthenic base of carbon number 3 to 20, the aryl of carbon number 6 to 20, assorted alkyl, the Heterocyclylalkyl of carbon number 3 to 20 or the heteroaryl of carbon number 3 to 20 of carbon number 1 to 20 independently of one another.
4. the photosensitive polymer combination for colored filter according to claim 1 and 2, wherein, described dyestuff is the compound being represented by following Chemical formula 2:
[Chemical formula 2]
Figure FDA0000489795290000031
In described Chemical formula 2,
M is copper, cobalt, aluminium, zinc, nickel, platinum or chromium;
N is nitrogen;
O is oxygen;
R ato R hbe the alkyl of carbon number 1 to 20, the naphthenic base of carbon number 3 to 20, the aryl of carbon number 6 to 20, assorted alkyl, the Heterocyclylalkyl of carbon number 3 to 20 or the heteroaryl of carbon number 3 to 20 of carbon number 1 to 20 independently of one another.
5. the photosensitive polymer combination for colored filter according to claim 1, wherein, described dyestuff is for being selected from least one compound in eight (2-ethyl hexyl oxy) copper phthalocyanine, eight (2-ethyl hexyl oxy) cobalt phthalocyanine, eight (2-ethyl hexyl oxy) aluminium phthalocyanine, eight (2-ethyl hexyl oxy) ZnPc, eight (2-ethyl hexyl oxy) nickel phthalocyanine, eight (2-ethyl hexyl oxy) platinum phthalocyanine and eight (2-ethyl hexyl oxy) chromium phthalocyanine.
6. the photosensitive polymer combination for colored filter according to claim 2, wherein, described dyestuff is for being selected from eight (1, 4, 7, 10-tetra-oxa-undecyls) copper phthalocyanine, eight (1, 4, 7, 10-tetra-oxa-undecyls) cobalt phthalocyanine, eight (1, 4, 7, 10-tetra-oxa-undecyls) aluminium phthalocyanine, eight (1, 4, 7, 10-tetra-oxa-undecyls) ZnPc, eight (1, 4, 7, 10-tetra-oxa-undecyls) nickel phthalocyanine, eight (1, 4, 7, 10-tetra-oxa-undecyls) platinum phthalocyanine, and eight (1, 4, 7, 10-tetra-oxa-undecyls) at least one compound in chromium phthalocyanine.
7. the photosensitive polymer combination for colored filter according to claim 1 and 2, with respect to the described binder resin of 100 weight portions, comprises:
The described reactive unsaturated compound of 100 to 250 weight portions;
The described pigment of 5 to 150 weight portions;
The described dyestuff of 50 to 250 weight portions;
The described polymerization initiator of 5 to 50 weight portions; And
The described solvent of 100 to 500 weight portions.
8. the photosensitive polymer combination for colored filter according to claim 1 and 2, wherein, described binder resin is a co-polymer, by 10 to 40wt% at least one have and be selected from (methyl) acrylic acid, Yi Kang acid, maleic acid, fumaric acid, vinyl acetic acid, 2-acrylyl oxy-ethyl phthalandione hydrogen ester, and the monomer of ethene acidic group in 2-acryloyl-oxy propyl group phthalandione hydrogen ester, and 60 to 90wt% at least one be selected from (methyl) isobutyl acrylate, (methyl) tert-butyl acrylate, (methyl) acrylic acid Lauryl Ester, ste(methyl) aryl-acrylic acid esters, (methyl) cyclohexyl acrylate, (methyl) isobornyl acrylate, (methyl) benzyl acrylate, (methyl) acrylic acid 2-hydroxy alkyl ester, (methyl) acrylic acid trimethoxy butyl ester, ethyl carbitol (methyl) acrylate, (methyl) phenoxyethyl acrylate, (methyl) acrylic acid 4-hydroxyl butyl ester, phenoxy group ethylene glycol (methyl) acrylate, (methyl) HEA, (methyl) acrylic acid 2-hydroxypropyl ester, 2-acryloxy ethyl 2-hydroxypropyl (methyl) phthalic ester, 2-hydroxyl-3-phenoxy propyl (methyl) acrylate, triethyl siloxy ethyl (methyl) methyl acrylate, and (methyl) acrylate monomer in ethyl triethylene glycol (methyl) acrylate is polymerized.
9. the photosensitive polymer combination for colored filter according to claim 1 and 2, wherein, described reactive unsaturated compound is for being selected from ethylene glycol bisthioglycolate (methyl) acrylate, diethylene glycol two (methyl) acrylate, triethylene glycol two (methyl) acrylate, propylene glycol two (methyl) acrylate, BDO two (methyl) acrylate, 1,6-hexanediol two (methyl) acrylate, neopentyl glycol two (methyl) acrylate, pentaerythrite two (methyl) acrylate, pentaerythrite three (methyl) acrylate, pentaerythrite four (methyl) acrylate, pentaerythrite five (methyl) acrylate, pentaerythrite six (methyl) acrylate, dipentaerythritol two (methyl) acrylate, dipentaerythritol three (methyl) acrylate, dipentaerythritol four (methyl) acrylate, dipentaerythritol five (methyl) acrylate, dipentaerythritol six (methyl) acrylate, bisphenol-A two (methyl) acrylate, trimethylolpropane tris (methyl) acrylate, phenolic aldehyde epoxy (methyl) acrylate, there is dipentaerythritol five (methyl) acrylate derivative of carboxyl, oxirane glycerine trimethylolpropane tris (methyl) acrylate, epoxypropane glycerine three (methyl) acrylate, epoxy (methyl) acrylate oligomer, amido formate (methyl) acrylate oligomer, sulfydryl (methyl) acrylate oligomer, and at least one compound in polyester (methyl) acrylate oligomer.
10. a colored filter, uses photosensitive polymer combination according to claim 1 and 2 made.
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08302224A (en) * 1995-04-28 1996-11-19 Yamamoto Chem Inc Phthalocyanine compound, its intermediate, method for producing the phthalocyanine compound, color filter using the phthalocyanine compound and oil ink composition
JP2002121412A (en) * 2000-10-17 2002-04-23 Nippon Shokubai Co Ltd Copper phthalocyanin modified pigment and method of producing the same
JP2003161821A (en) * 2000-12-22 2003-06-06 Mitsubishi Chemicals Corp Composition for color filter, and the color filter
JP2004157455A (en) * 2002-11-08 2004-06-03 Fuji Photo Film Co Ltd Dye-containing hardening composition, color filter and its manufacturing method
JP2006058700A (en) * 2004-08-20 2006-03-02 Fuji Photo Film Co Ltd Colored curable composition, color filter and method for producing same

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08302224A (en) * 1995-04-28 1996-11-19 Yamamoto Chem Inc Phthalocyanine compound, its intermediate, method for producing the phthalocyanine compound, color filter using the phthalocyanine compound and oil ink composition
JP2002121412A (en) * 2000-10-17 2002-04-23 Nippon Shokubai Co Ltd Copper phthalocyanin modified pigment and method of producing the same
JP2003161821A (en) * 2000-12-22 2003-06-06 Mitsubishi Chemicals Corp Composition for color filter, and the color filter
JP2004157455A (en) * 2002-11-08 2004-06-03 Fuji Photo Film Co Ltd Dye-containing hardening composition, color filter and its manufacturing method
JP2006058700A (en) * 2004-08-20 2006-03-02 Fuji Photo Film Co Ltd Colored curable composition, color filter and method for producing same

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CN115003775A (en) * 2019-11-04 2022-09-02 Kd精细化工有限公司 Colorants for heat transfer fluids and compositions containing the same
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CN103890658B (en) 2017-12-05
TW201321802A (en) 2013-06-01

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