CN110073253A - Colour filter resin combination, the manufacturing method of colour filter resin combination and colour filter - Google Patents

Colour filter resin combination, the manufacturing method of colour filter resin combination and colour filter Download PDF

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Publication number
CN110073253A
CN110073253A CN201780077149.1A CN201780077149A CN110073253A CN 110073253 A CN110073253 A CN 110073253A CN 201780077149 A CN201780077149 A CN 201780077149A CN 110073253 A CN110073253 A CN 110073253A
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methyl
colour filter
mass parts
resin combination
solvent
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CN110073253B (en
Inventor
仓本拓树
川口恭章
木下健宏
柳正义
原司
永井英理
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Lishennoco Co ltd
Resonac Holdings Corp
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Showa Denko KK
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
    • C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F246/00—Copolymers in which the nature of only the monomers in minority is defined
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • 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
    • G03F7/075—Silicon-containing 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
    • G03F7/075—Silicon-containing compounds
    • G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
    • G03F7/0758—Macromolecular compounds containing Si-O, Si-C or Si-N bonds with silicon- containing groups in the side chains

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Materials For Photolithography (AREA)
  • Optical Filters (AREA)
  • Liquid Crystal (AREA)

Abstract

A kind of colour filter resin combination, contains: the specific copolymer of (A) containing structural unit shown in following formula (1)；(B) solvent of the hydroxyl solvent containing carbon atom number 3~10；(C) reactive diluent；(D) Photoepolymerizationinitiater initiater；And (E) colorant.In formula (1), R1Indicate hydrogen atom or methyl, R2~R4The alkoxy of hydrogen atom, the alkyl of carbon atom number 1~6 or carbon atom number 1~6 is each independently represented, n is the integer in 1~10.Wherein, R2~R4At least one of be carbon atom number 1~6 alkoxy.

Description

Colour filter resin combination, colour filter resin combination manufacturing method and Colour filter
Technical field
The present invention relates to the manufacturing methods and colour filter of a kind of colour filter resin combination, colour filter resin combination Device.
Background technique
In recent years, from the viewpoint of saving resource, energy conservation, in the fields such as various coatings, printing, coating, bonding agent, Cured photosensitive polymer combination can be carried out by ultraviolet light, electron beam isoreactivity energy-ray to be widely used.In addition, In the field of the electronic materials such as printed circuit board, cured photosensitive polymer combination can be carried out by active energy beam It is used for solder resist (solder resist), colour filter resist (resist) etc..
Colour filter usually by the transparent substrates such as glass substrate, the red being formed on transparent substrate (R), green (G) and The pixel of blue (B), be formed in pixel boundary black matrix" and the protective film structure that is formed on pixel and black matrix" At.The colour filter of such composition is usually made by sequentially forming black matrix", pixel and protective film on the transparent substrate It makes.It is open as pixel and the forming method of black matrix" (hereinafter, pixel and black matrix" are known as " colored pattern ") Various methods.As the forming method of colored pattern, for example, pigment/dye dispersion method can be enumerated comprising: it will be photosensitive Property resin combination be used as resist, repeat the light of coating, exposure, development and the baking of the photosensitive polymer combination Lithography.The pigment/dye dispersion method can form the excellent in te pins of durability such as light resistance, heat resistance, and color-patch map few the defects of pin hole Case, therefore be currently widely used.
It is commonly used for that photolithographic photosensitive polymer combination contains alkali soluble resins, reactive diluent, photopolymerization are drawn Send out agent, colorant and solvent.
Pigment/dye dispersion method have above advantages, on the other hand, due to be concatenated to form black matrix", R, G, B it is each The pattern of pixel, therefore to the demanding resistance to pyrolytic of the alkali soluble resins of the adhesive as film and heat-resisting xanthochromia. As the new material for meeting the requirement, the inventors of the present invention propose ester ring type monomer and with ethoxylation o-phenyl phenol (methyl) Acrylate (that is, 2- phenylphenoxy ethyl (methyl) acrylate) be representative have from alkylene oxide structure and The copolymer (for example, referring to patent document 1) of (methyl) acrylate of aromatic yl residue.
In addition, in general, liquid crystal display device passes through in the filter substrate and TFT (Thin- individually produced Film-Transistor: thin film transistor (TFT)) liquid crystal is sandwiched between substrate, and make the fitting of these components to manufacture.Make these structures When part is bonded, the alignment films such as the polyimide film for making liquid crystal aligning are equipped in filter substrate.At this point, color-filter layer exposure In the high solvent of N-Methyl pyrrolidone (NMP) isopolarity contained in polyimide resin, therefore color-filter layer is wanted Ask solvent resistance (resistance to NMP).
Recently, for further high brightness, high-res, the coloured material in pixel becomes dyestuff, contains concentration Also it gets higher.But the dissolubility of dyestuff in a solvent is higher than pigment, dyestuff is eluted in the process in exposed solvent, is deposited It changes this problem in the coloration of pixel, is required improved solvent resistance containing the pixel there are many dyestuff.In addition, filtering Color device layer is exposed in the process of NMP equal solvent, reaches 40 DEG C or more of condition, the evaluation of the resistance to NMP of colour filter sometimes Test also carries out under high temperature (50 DEG C or more).
Thus, for example, proposing: being come using the copolymer with epoxy group or oxetanyl and carboxyl or phenolic hydroxyl group Improve the method for solvent resistance (for example, referring to patent document 2 and 3)；Using containing with the oxadiazoles comprising trihalomethyl The substance of the molecule of structure or triazine structure improves the method for solvent resistance as polymerization initiator (for example, referring to patent text 4) etc. it offers, but their solvent resistance is insufficient.
In addition, needing to increase joined together to improve the color reproduction of colour filter (color reproduction) characteristic Colorant content, or thicken film thickness etc., but these can have reduction, the reduction of developability etc. for generating sensitivity simultaneously The tendency of problem, it is desirable that further performance improves (for example, referring to patent document 5).
Existing technical literature
Patent document
Patent document 1: International Publication No. 2012/141000
Patent document 2: Japanese Unexamined Patent Publication 2012-22048 bulletin
Patent document 3: Japanese Unexamined Patent Publication 2013-25203 bulletin
Patent document 4: Japanese Unexamined Patent Publication 2003-330184 bulletin
Patent document 5: Japanese Unexamined Patent Publication 2014-164021 bulletin
Summary of the invention
Problem to be solved by the invention
The present invention be completed to solve above-mentioned such problems, it is intended that provide a kind of offer sensitivity, Developability is good, and the colour filter resin combination of the colored pattern of excellent solvent resistance.In addition, it is intended that mentioning For a kind of colour filter of colored pattern with excellent solvent resistance.
The solution to the problem
The inventors of the present invention have made intensive studies to solve the above-mentioned problems, as a result, it has been found that following fact, until complete At the present invention: containing specific copolymer, specific solvent, reactive diluent, Photoepolymerizationinitiater initiater and colorant Resin combination can solve the above problem.
That is, the present invention is indicated by [1] below~[5].
[1] a kind of colour filter resin combination, which is characterized in that contain: (A) copolymer has acidic group containing being originated from The structural unit (a-1) of polymerizable unsaturated compound, structural unit (a-2) shown in following formula (1) and be originated from it The structural unit (a-3) of his polymerizable unsaturated compound contains when entire infrastructure unit total is set as 100 moles of % There is the structural unit (a-2) of 1 mole of %~50 mole %, weight average molecular weight is 1000~50000 and molecular weight distribution (Mw/ It Mn) is 1.5~3.0；(B) solvent, the hydroxyl solvent containing carbon atom number 3~10；(C) reactive diluent；(D) photopolymerization Initiator；And (E) colorant.
(in formula (1), R1Indicate hydrogen atom or methyl, R2~R4Each independently represent hydrogen atom, carbon atom number 1~6 Alkyl or carbon atom number 1~6 alkoxy, n be 1~10 in integer.Wherein, R2~R4At least one of for carbon it is former The alkoxy of subnumber 1~6.)
[2] the colour filter resin combination according to [1], wherein the acidic group of the structural unit (a-1) is carboxylic Base, (A) copolymer contain the structural unit (a-1) of 10 moles of %~50 mole %, and (A) copolymer Acid value be 20KOHmg/g~300KOHmg/g.
[3] the colour filter resin combination according to [1] or [2], wherein will be other than (B) solvent The summation of ingredient when being set as 100 mass parts, the content of (A) copolymer is 5 mass parts~85 mass parts, and (C) is anti- The content of answering property diluent is 5 mass parts~85 mass parts, and the content of (D) Photoepolymerizationinitiater initiater is 0.1 mass parts~30 Mass parts, the content of (E) colorant are 5 mass parts~75 mass parts.
[4] a kind of colour filter, which is characterized in that there is the colour filter resin combination as described in any one of [1]~[3] The colored pattern that object is formed.
[5] a kind of manufacturing method of colour filter resin combination characterized by comprising make to have containing (A-1) There are polymerizable unsaturated compound, (A-2) following formula (2) compound represented and (A-3) other polymerisms of acidic group not The monomer mixture of saturated compounds, after being copolymerized in the presence of (B) solvent, addition (C) reactive diluent, (D) light are poly- Close initiator and (E) colorant and mixed process, wherein by (A-1) compound, (A-2) compound and (A- 3) when compound total is set as 100 moles of %, monomer mixture contains (A-2) compound of 1 mole of %~50 mole %, And (B) solvent contains the hydroxyl solvent of carbon atom number 3~10.
(in formula (2), R1Indicate hydrogen atom or methyl, R2~R4Each independently represent hydrogen atom, carbon atom number 1~6 Alkyl or carbon atom number 1~6 alkoxy, n be 1~10 in integer.Wherein, R2~R4At least one of for carbon it is former The alkoxy of subnumber 1~6.)
Invention effect
According to the present invention, it is good that a kind of offer sensitivity, developability can be provided, and the colored pattern of excellent solvent resistance Colour filter resin combination.In addition, according to the present invention, a kind of filter of colored pattern with excellent solvent resistance can be provided Color device.
Detailed description of the invention
Fig. 1 is the summary section for indicating the colour filter of one embodiment of the present invention.
Specific embodiment
Colour filter resin combination of the invention contains (A) copolymer, (B) solvent, (C) reactive diluent, (D) light Polymerization initiator and (E) colorant.
[(A) copolymer]
(A) copolymer in the present invention contains: the structural unit from the polymerizable unsaturated compound with acidic group (a-1), structural unit (a-2) and the structural unit from other polymerizable unsaturated compounds shown in following formula (1) (a-3).
(in formula (1), R1Indicate hydrogen atom or methyl, R2~R4Each independently represent hydrogen atom, carbon atom number 1~6 Alkyl or carbon atom number 1~6 alkoxy, n be 1~10 in integer.Wherein, R2~R4At least one of for carbon it is former The alkoxy of subnumber 1~6.)
For (A) copolymer in the present invention, by structural unit (a-1), structural unit (a-2) and structure list When first (a-3) total is set as 100 moles of %, the structural unit (a-2) containing 1 mole of %~50 mole %.When structure list The containing ratio of first (a-2) then cannot get desired solvent resistance less than 1 mole of % or when being greater than 50 moles of %.Structure The containing ratio of unit (a-2) is preferably 5 moles of %~40 mole %, more preferably 10 moles of %~30 mole %.In addition, (A) copolymer in the present invention preferably comprises the structural unit (a-1) of 10 moles of %~50 mole %, and further preferably 15 rub The structural unit (a-1) of your %~45 mole %, the structural unit (a-1) of most preferably 20 moles %~40 mole %. When the containing ratio of structural unit (a-1) within the above range when, can be obtained more good developability.In addition, in the present invention (A) copolymer preferably comprises the structural unit (a-3) of 1 mole of %~89 mole %, and further preferably 15 moles of %~80 are rubbed The structural unit (a-3) of your %, the structural unit (a-3) of most preferably 30 moles %~70 mole %.Work as structural unit (a-3) containing ratio within the above range when, more good developability and solvent resistance can be obtained.
It should be noted that the weight average molecular weight (Mw) of (A) copolymer is calculated as 1000~50000 by polystyrene conversion, Preferably 2000~40000, more preferably 3000~30000.When the weight average molecular weight (Mw) of (A) copolymer is less than 1000, After development, colored pattern generates defect.On the other hand, it when the weight average molecular weight (Mw) of (A) copolymer is greater than 50000, shows The shadow time becomes too long, loses practicability.The value of the weight average molecular weight (Mw) of (A) copolymer in the present invention is seeped using gel Saturating chromatography (GPC) determines under the following conditions and goes out by polystyrene Conversion Calculation.
Column: SHOWDEX (registered trademark) LF-804+LF-804 (Showa Denko K. K's system)
Column temperature: 40 DEG C
Sample: the content of (A) copolymer is the tetrahydrofuran solution of 0.2 mass %
Developing solvent: tetrahydrofuran
Detector: differential refractometer (trade name: SHOWDEX (registered trademark) RI-71S, Showa Denko K. K's system)
Flow velocity: 1mL/min
The molecular weight distribution (Mw/Mn) of (A) copolymer in the present invention is 1.5~3.0, preferably 1.5~2.8, more excellent It is selected as 1.5~2.6.When the molecular weight distribution (Mw/Mn) of (A) copolymer is less than 1.5, it is necessary to accurately set weight average molecular weight With the reaction condition etc. when optimization, manufacture (A) copolymer of the target values range such as acid value, imitated from the working hour of research and gained The balance consideration of fruit is unpractical.On the other hand, when the molecular weight distribution (Mw/Mn) of (A) copolymer is greater than 3.0, development Property generate deviation.Mw/Mn is measured according to the chromatogram that above-mentioned GPC is measured.
The acid value of (A) copolymer in the present invention is not particularly limited, preferably 20KOHmg/g~300KOHmg/g, more Preferably 30KOHmg/g~200KOHmg/g.If the acid value of (A) copolymer is 20KOHmg/g or more, can be obtained more good Developability.On the other hand, if the acid value of (A) copolymer be 300KOHmg/g hereinafter, if exposed portion (photo-cured portion) it is insoluble Solution is in alkaline-based developer.
It should be noted that the acid value of (A) copolymer refers to, bromthymol blue and phenol are used according to JIS K6901 5.3 Red mixed indicator and the value determined, hydroxide needed for referring to acid ingredient contained in neutralization (A) copolymer 1 g The mg number of potassium.
In the case that (A) copolymer in the present invention has unsaturated group, unsaturated group equivalent is not special It limits, preferably 100g/mol~4000g/mol, more preferably 200g/mol~3000g/mol.The insatiable hunger of (if A) copolymer It is 100g/mol or more with group equivalent, then is effective for further increasing resistance to pyrolytic and heat-resisting xanthochromia.Separately On the one hand, if the unsaturated group equivalent of (A) copolymer be 4000g/mol hereinafter, if be to have for further increasing sensitivity Effect.
The silylation equivalent of (A) copolymer in the present invention is not particularly limited, preferably 400g/mol~4000g/ Mol, more preferably 500g/mol~3000g/mol.If the silylation equivalent of (A) copolymer is 400g/mol or more, for It is effective for further increasing resistance to pyrolytic and heat-resisting xanthochromia.On the other hand, if the silylation equivalent of (A) copolymer is 4000g/mol is hereinafter, be then effective for further increasing solvent resistance.
It should be noted that the silylation equivalent of (A) copolymer is average divided by the silylation in each molecule The molecular weight of (A) copolymer after number, using the calculated calculated value of charge weight for being based on aftermentioned (A-2) compound.
Above-mentioned (A) copolymer can pass through the presence of the solvent in the hydroxyl solvent of (B) containing carbon atom number 3~10 Under, make to have containing (A-1) polymerizable unsaturated compound of acidic group, (A-2) following formula (2) compound represented and (A-3) monomer mixture of other polymerizable unsaturated compounds, according to well known free radical polymerisation process in the technical field Copolymerization is to prepare.
(in formula (2), R1Indicate hydrogen atom or methyl, R2~R4Each independently represent hydrogen atom, carbon atom number 1~6 Alkyl or carbon atom number 1~6 alkoxy, n be 1~10 in integer.Wherein, R2~R4At least one of for carbon it is former The alkoxy of subnumber 1~6.).For example, being dissolved in by (A-1) compound, (A-2) compound and (A-3) compound (B) solvent after preparing solution, adds polymerization initiator into the solution, reacts it 1 hour ~20 hours.(A) sequence that the number of iterations of each compound in copolymer, respective compound are combined is not special It limits.Alternatively, it is also possible to prepare without containing structural unit (a-1), structural unit (a-2) and structural unit (a-3) Any of copolymer after, the structural unit lacked is directed into copolymer by modified-reaction, is thus prepared Copolymer containing structural unit (a-1), structural unit (a-2) and structural unit (a-3).
(A-1) acidic group of the polymerizable unsaturated compound with acidic group is not particularly limited, but generally preferable carboxyl, Phosphate (- O-P (=O) (OH)2), sulfonic group (- S (=O)2OH) etc..Wherein, there is the polymerism of acidic group as (A-1) The acidic group of unsaturated compound, from the viewpoint of reactivity, particularly preferred carboxyl.
(A-1) polymerizable unsaturated compound with acidic group is if the monomer with acidic group and ethylenically unsaturated group, Then it is not particularly limited.As the concrete example of (A-1) compound, for example, can enumerate: (methyl) acrylic acid, crotonic acid, meat Cinnamic acid, vinyl sulfonic acid, 2- (methyl) acryloyl-oxyethyl succinic acid, 2- acryloyl-oxyethyl phthalic acid, 2- (methyl) acryloyl-oxyethyl hexahydrophthalic acid, 2- (methyl) acryloyl-oxyethyl superphosphate etc..Wherein, From the viewpoint of the easness of acquisition and reactivity, preferred (methyl) acrylic acid.It should be noted that in the present invention, " (methyl) acrylic acid " refers to selected from least one of methacrylic acid and acrylic acid." (methyl) acrylate " is also same Sample.
As the concrete example of (A-2) above-mentioned formula (2) compound represented, for example, can enumerate: 3- (methyl) acryloyl Oxygroup hydroxypropyl methyl dimethoxysilane, 3- (methyl) acryloxypropyl ethyldimethoxysilane, 3- (methyl) third Alkene methyl diethoxy silane, 3- (methyl) acryloxypropyl ethyl diethoxy silane, 3- (first Base) acryloyloxypropyltrimethoxysilane, 3- (methyl) acryloxypropyl triethoxysilane etc..Wherein, from obtaining From the viewpoint of the easness and reactivity that take, preferably 3- (methyl) acryloyloxypropyltrimethoxysilane and 3- (methyl) acryloxypropyl triethoxysilane.
(A-3) other polymerizable unsaturated compounds be polymerism other than (A-1) ingredient and (A-2) ingredient not Saturated compounds is without acidic group, silylation and can be with the polymerism of (A-1) compound and (A-2) copolymer compound Unsaturated compound.As the concrete example of (A-3) other polymerizable unsaturated compounds, for example, can enumerate: butadiene etc. Dienes；(methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) n-propyl, (methyl) acrylic acid isopropyl Ester, (methyl) n-butyl acrylate, (methyl) sec-butyl acrylate, (methyl) isobutyl acrylate, the tertiary fourth of (methyl) acrylic acid Ester, (methyl) amyl acrylate, (methyl) acrylic acid peopentyl ester, (methyl) benzyl acrylate, (methyl) isoamyl acrylate, (methyl) Hexyl 2-propenoate, (methyl) 2-EHA, (methyl) benzyl acrylate, (methyl) lauryl acrylate, (methyl) dodecylacrylate, (methyl) acrylic acid ring pentyl ester, (methyl) cyclohexyl acrylate, (methyl) propylene acid methyl Cyclohexyl, (methyl) acrylic acid ethyl cyclohexyl, 1,4-CHDM list (methyl) acrylate, rosin (methyl) third Olefin(e) acid ester, (methyl) acrylic acid norbornyl ester, (methyl) acrylic acid 5- methyl norbornyl ester, (methyl) acrylic acid 5- ethyl drop Norbornene ester, (methyl) allyl acrylate, (methyl) tetrahydrofurfuryl acrylate, (methyl) acrylic acid 1,1,1- trifluoro ethyl ester, (methyl) perfluoroethyl ethyl ester, (methyl) perfluoroethyl n-propyl, (methyl) perfluoroethyl isopropyl ester, (methyl) propylene Triphenyl phosphate base methyl esters, (methyl) acrylic acid cumyl ester, (methyl) acrylic acid 3- (N, N- dimethylamino) propyl ester, glycerine list (methyl) acrylate, butantriol list (methyl) acrylate, penta triol list (methyl) acrylate, two ring of (methyl) acrylic acid Amylene ester, (methyl) dicyclopentanyl acrylate, (methyl) isobornyl acrylate, (methyl) acrylic acid Buddha's warrior attendant alkyl ester, (methyl) Acrylic acid naphthalene ester, (methyl) acrylic acid anthracene ester, (methyl) acrylic acid 2- (2- vinyloxyethoxy) ethyl ester, (methyl) propylene Acid glycidyl ester, (methyl) acrylic acid 3,4- epoxycyclohexanecarboxylate, (methyl) acrylic acid (3- Ethyloxetane- 3- yl) methyl esters, (methyl) acrylic acid 2- isocyanatoethyl methacrylate, (methyl) acrylic acid 2- isocyanate group propyl ester, (methyl) propylene Sour 3- isocyanate group propyl ester, (methyl) acrylic acid 2- isocyanate group -1- Methylethyl, (methyl) acrylic acid 2- isocyanic acid Base -1,1- dimethylethyl esters, (methyl) acrylic acid 4- isocyanate group cyclohexyl have isocyanide to described using end-capping reagent The isocyanate group of the olefinic unsaturated compound of acidic group carries out the compound, (first obtained by sealing end with blocked terminal isocyanate groups Base) acrylic acid N, N- dimethylamino ethyl ester, (methyl) acrylic acid N, N- diethylamino ethyl ester, (methyl) acrylic acid N- (methyl) propylene such as t-butylaminoethyl, (methyl) acrylic acid tetramethyl piperidine ester, (methyl) acrylic acid hexamethyl piperidine ester Esters of gallic acid；(methyl) acrylic acid amides, (methyl) acrylic acid N, N- dimethylformamide, (methyl) acrylic acid N, N- diethyl acyl Amine, (methyl) acrylic acid N, N- dipropyl amide, bis--Isopropyl amide of (methyl) acrylic acid N, N-, (methyl) acrylic acid anthracene (methyl) such as base amide, N- isopropyl (methyl) acrylamide, (methyl) acrylic acid morpholine, diacetone (methyl) acrylamides Acrylic acid amides class；Norbornene (bicyclic [2.2.1] hept-2-ene"), 5- methyl bicycle [2.2.1] hept-2-ene", 5- second Bicyclic [2.2.1] hept-2-ene" of base, Fourth Ring [4.4.0.12,5.17,10] 12 carbon -3- alkene, 8- methyl Fourth Ring [4.4.0.12 ,5.17,10] 12 carbon -3- alkene, 8- ethyltetracyclo [4.4.0.12,5.17,10] 12 carbon -3- alkene, bicyclopentadiene, tricyclic [5.2.1.02,6] decyl- 8- alkene, tricyclic [5.2.1.02,6] decyl- 3- alkene, tricyclic [4.4.0.12,5] 11 carbon -3- alkene, three Ring [6.2.1.01,8] 11 carbon -9- alkene, tricyclic [6.2.1.01,8] 11 carbon -4- alkene, Fourth Ring [4.4.0.12,5.17, 10.01,6] 12 carbon -3- alkene, 8- methyl Fourth Ring [4.4.0.12,5.17,10.01,6] 12 carbon -3- alkene, 8- ethylidene four Ring [4.4.0.12,5.17,12] 12 carbon -3- alkene, 8- ethylidene Fourth Ring [4.4.0.12,5.17,10.01,6] 12 carbon -3- Alkene, five rings [6.5.1.13,6.02,7.09,13] pentadecane -4- alkene, five rings [7.4.0.12,5.19,12.08,13] pentadecane -3- Alkene, 5- norbornene -2,3- dicarboxylic anhydride, (methyl) acrylic acid anilide, (methyl) propylene acyl cyanide, methacrylaldehyde, chloroethene The vinyl compounds such as alkene, vinylidene chloride, vinyl fluoride, vinylidene, vinylpyridine, vinyl acetate, vinyltoluene；Benzene Ethylene, the α-of styrene, o-, m-, p- alkyl, nitro, cyano, amide derivatives；Citraconic acid diethylester, maleic acid The unsaturated dicarboxylics diester such as diethylester, diethyl fumarate, diethyl itaconate；Maleic anhydride, itaconic anhydride, citraconic anhydride Deng unsaturated multi-anhydride etc..Wherein, from the viewpoint of the easness of acquisition and reactivity, preferred (methyl) acrylic acid first Ester, (methyl) 2-EHA, (methyl) benzyl acrylate, (methyl) dicyclopentanyl acrylate, (methyl) acrylic acid Ethylene oxidic ester, (methyl) acrylic acid (3- Ethyloxetane -3- base) methyl esters, (methyl) acrylic acid N, N- diethyl Amino ethyl ester, (methyl) acrylic acid N, N- dimethylformamide, (methyl) acrylic acid morpholine, styrene, vinyltoluene and drop Bornylene, more preferable (methyl) methyl acrylate, (methyl) benzyl acrylate, (methyl) dicyclopentanyl acrylate, (methyl) third Olefin(e) acid ethylene oxidic ester, (methyl) acrylic acid (3- Ethyloxetane -3- base) methyl esters, styrene and vinyl first Benzene.These (A-3) compounds can be used alone, and can also be applied in combination two or more.Wherein, from resistance to pyrolytic And from the viewpoint of heat-resisting xanthochromia, preferred (methyl) alkyl acrylate, more preferable (methyl) methyl acrylate, (methyl) Benzyl acrylate, (methyl) dicyclopentanyl acrylate.In addition, preferably having and acidic group from the viewpoint of improving solvent resistance The polymerizable compound of the functional group of reaction, specifically, can enumerate with glycidyl, oxetanyl, isocyanide The polymerizable compound of acidic group (isocyanato group) or blocked terminal isocyanate groups.It is further preferred that being easy from acquisition From the viewpoint of degree and reactivity, (methyl) glycidyl acrylate, methacrylic acid (3- ethyl oxa- can be enumerated Cyclobutane -3- base) methyl esters etc..
As the end-capping reagent of the sealing end for above-mentioned isocyanate group, for example, can enumerate: in epsilon-caprolactams, δ-penta The lactams such as amide, butyrolactam, azetidinone system；The molten fibre of methanol, ethyl alcohol, propyl alcohol, butanol, ethylene glycol, methyl The alcohol such as agent, butyl cellosolve, methyl carbitol, benzylalcohol, ethylene glycol monophenyl ether, furfuryl alcohol, cyclohexanol system；Phenol, cresols, xylenol, The butylphenols such as ethyl -phenol, o-isopropyl phenol, p-tert-butylphenol, to tert-octyl phenol, nonyl phenol, dinonyl benzene Phenol, styrenated phenol, oxybenzoic acid ester, thymol, to phenol systems such as naphthols, p-nitrophenol, parachlorophenols；Malonic acid dimethyl Ester, diethyl malonate, methyl acetoacetate, ethyl acetoacetate, acetylacetone,2,4-pentanedione isoreactivity methylene base system；Butanethiol, benzene The mercaptan such as thiophenol, tert-dodecylmercaotan system；The amine systems such as diphenylamines, nonox, aniline, carbazole；Antifebrin, methoxyl group second The acid amide such as anilide, amide, benzamide system；The acid imides systems such as bromosuccinimide, Malaysia acid imide；Miaow The imidazoles systems such as azoles, 2-methylimidazole, 2- ethyl imidazol(e)；The ureas such as urea, thiocarbamide, ethylidene-urea system；N- phenylcarbamic acid benzene The carbaminates systems such as ester, 2- oxazolidone；The imines such as ethylenimine, polyethylene imine system；Formaldoxime, acetaldoxime, third The oximes such as ketoxime, methyl ethyl ketone oxime, methyl isobutyl ketoxime, cyclohexanone oxime system；The sulfurous acid such as sodium hydrogensulfite, potassium bisulfite Hydrogen salt system etc..
For same as above-mentioned structural unit (the a-1)~containing ratio of (a-3) for defining composition (A) copolymer The reasons why, it is single when (A-1) compound, (A-2) compound and (A-3) compound total is set as 100 moles of % Body mixture preferably comprises (A-1) compound of 10 moles of %~50 mole %, further preferably 15 moles of %~45 mole % (A-1) compound, (A-1) compound of most preferably 20 moles %~40 mole %.Similarly, change by (A-1) Close object, (A-2) compound and (A-3) compound it is total when being set as 100 moles of %, monomer mixture contains 1 mole of % (A-2) compound of~50 moles of %, preferably comprises (A-2) compound of 5 moles of %~40 mole %, and further preferably 10 (A-2) compound of mole %~30 mole %.Similarly, by (A-1) compound, (A-2) compound and (A-3) When compound total is set as 100 moles of %, monomer mixture preferably comprises (A-3) chemical combination of 1 mole of %~89 mole % Object, (A-3) compound of further preferably 15 moles %~80 mole %, most preferably 30 moles of %~70 mole %'s (A-3) compound.
It controls from by the weight molecular weight of (A) copolymer and molecular weight distribution (Mw/Mn) in defined range, and To from the viewpoint of the colored pattern with desired solvent resistance, for needing in (B) solvent of copolyreaction containing carbon The hydroxyl solvent of atomicity 3~10.It is copolymerized when using the solvent of the hydroxyl solvent without containing carbon atom number 3~10 When reaction, it may occur that the weight molecular weight and molecular weight distribution (Mw/Mn) of gelation or resulting copolymer are not providing In the range of.Wherein, from the viewpoint of control molecular weight distribution, preferably with the solvent of a hydroxyl.As carbon atom number 3 The concrete example of~10 hydroxyl solvent, for example, can enumerate: propyl alcohol, butanol, amylalcohol, hexanol, octanol, nonyl alcohol, decyl alcohol, ten The single methanols class such as dialkanol, benzylalcohol；Glycol monoethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, Diethylene glycol list positive propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, Triethylene glycol ethyl ether, propylene glycol monomethyl ether, Dihydroxypropane single-ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol list positive propyl ether, dipropylene glycol mono-n-butyl ether, (poly-) alkylene glycol monoalkyl ethers classes such as Tripropylene glycol monomethyl Ether, tripropylene glycol list ether etc..These carbon atom numbers 3~10 Hydroxyl solvent can be used alone, and can also be applied in combination two or more.In addition, in above-mentioned alcohol, for example, third In alcohol, by other than 1- propyl alcohol also containing 2- propyl alcohol in a manner of contain various isomers.
Other solvents can also be contained in (B) solvent for copolyreaction.As other solvents, for example, can enumerate Out: ethylene glycol monomethyl ether acetate, ethylene glycol monoethylether acetate, propylene glycol methyl ether acetate, dihydroxypropane single-ether acetic acid Ester etc. (poly-) alkylene glycol monoalkyl ethers acetate esters；Diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol Other ethers such as diethyl ether, tetrahydrofuran；The ketones such as methyl ethyl ketone, cyclohexanone, 2-HEPTANONE, 3- heptanone；2 hydroxy propanoic acid Methyl esters, 2 hydroxy propanoic acid ethyl ester, 2- hydroxy-2-methyl methyl propionate, 2- hydroxy-2-methyl ethyl propionate, 3- first Oxygroup methyl propionate, 3- methoxypropionate, 3- ethoxypropanoate, 3- ethoxyl ethyl propionate, ethoxyacetic acid Ethyl ester, hydroxyl ethyl acetate, 2- hydroxy-3-methyl methyl butyrate, 3- methyl -3- methoxybutyl acetic acid esters, 3- first Base -3- methoxybutyl propionic ester, ethyl acetate, n-butyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, Isobutyl acetate, n-amyl acetate, isoamyl acetate, n-butyl propionate, ethyl butyrate, propyl butyrate, isopropyl isobutyrate, fourth Sour N-butyl, methyl pyruvate, ethyl pyruvate, pyruvic acid n-propyl, methyl acetoacetate, ethyl acetoacetate, 2- oxo The esters such as ethyl butyrate；Toluene, dimethylbenzene etc. are aromatic hydrocarbon；N-Methyl pyrrolidone, n,N-Dimethylformamide, N, Carboxylic acyloxies amine such as N- dimethyl acetamide etc..Wherein, from the viewpoint of reactivity, preferred propylene glycol methyl ether acetate Deng (poly-) alkylene glycol monoalkyl ethers acetic acid ester series solvent.
Relative to (B) solvent for copolyreaction, the containing ratio of the hydroxyl solvent of carbon atom number 3~10 is preferably The 10 mass % of mass %~100, more preferably 20 mass of mass %~100 %.When the hydroxyl solvent of carbon atom number 3~10 Containing ratio within the above range when, it is easier to the weight molecular weight of (A) copolymer and molecular weight distribution (Mw/Mn) are controlled In defined range, the solvent resistance of colored pattern can be further improved.
The usage amount of (B) solvent in copolyreaction is not particularly limited, but by (A-1) compound, (A-2) chemical combination When the charge weight of object and (A-3) compound total is set as 100 mass parts, preferably 30 mass parts~1000 mass parts, more Preferably 50 mass parts~800 mass parts.
By the way that the usage amount of (B) solvent is set as 30 mass parts or more, abnormal polymerization reaction can be prevented, is steadily carried out Polymerization reaction, and the coloring of (A) copolymer, gelation can also be prevented.In addition, by the way that the usage amount of (B) solvent is set as 1000 below the mass, can inhibit the reduction of the molecular weight of (A) copolymer as caused by chain transfer, and (A) is copolymerized The viscosity of object is controlled in range appropriate.
It as the polymerization initiator that can be used for the copolyreaction, is not particularly limited, such as can enumerate: 2,2 '-azos Two (isobutyronitriles), 2,2 '-azos two (2,4- methyl pentane nitrile), 2,2 '-azo two (isobutyric acid) dimethyl esters, benzoyl peroxide Formyl, t-butyl peroxy -2 ethyl hexanoic acid ester etc..These polymerization initiators can be used alone, and can also combine makes With two or more.
The usage amount of polymerization initiator is not particularly limited, but by (A-1) compound, (A-2) compound and (A-3) when the charge weight of compound total is set as 100 mass parts, preferably 0.5 mass parts~20 mass parts, more preferably 1.0 mass parts~10 mass parts.
For the use level of (A) copolymer in colour filter resin combination of the invention, used by the colour filter When the summation of the ingredient other than (B) solvent in resin combination is set as 100 mass parts, preferably 5 mass parts~85 matter Measure part, more preferably 15 mass parts~75 mass parts, most preferably 20 mass parts~65 mass parts.When the cooperation of (A) copolymer When measuring within the above range, the curability of colour filter resin combination becomes more appropriate.
[(B) solvent]
(B) solvent being matched in colour filter resin combination of the invention can be used directly and prepare above-mentioned (A) Above-mentioned exemplified (B) solvent can also be further added in solvent used in (copolyreaction) when copolymer.In addition, When other compositions are added, it can be and coexist in solvent therein.
For the use level of (B) solvent in colour filter resin combination of the invention, by the colour filter tree When the summation of the ingredient other than (B) solvent in oil/fat composition is set as 100 mass parts, preferably 30 mass parts~1000 matter Measure part, more preferably 50 mass parts~800 mass parts, most preferably 100 mass parts~700 mass parts.When the cooperation of (B) solvent When measuring within the above range, the viscosity of colour filter resin combination becomes more appropriate.
[(C) reactive diluent]
As (C) reactive diluent being matched in colour filter resin combination of the invention, it is not particularly limited, But preferably comprise the substance of ethylenical unsaturated double bonds, vinyl, (methyl) acryloxy.As (C) reactive diluent Concrete example, for example, can enumerate: styrene, α-methylstyrene, α -1-chloro-4-methyl-benzene, vinyltoluene, divinyl The aromatic vinyls base system monomer class such as benzene, diallyl phthalate, phosphniline diallyl phthalate；Vinyl acetate, adipic acid The polycarboxylic acids monomer class such as vinyl acetate；(methyl) methyl acrylate, (methyl) ethyl acrylate, (methyl) propyl acrylate, (first Base) butyl acrylate, (methyl) propenoic acid beta-hydroxy base ethyl ester, (methyl) hydroxypropyl acrylate, ethylene glycol two (methyl) propylene Acid esters, diethylene glycol two (methyl) acrylate, propylene glycol two (methyl) acrylate, ethylene glycol two (methyl) acrylate, Trimethylolpropane two (methyl) acrylate, trimethylolpropane tris (methyl) acrylate, pentaerythrite four (methyl) third Olefin(e) acid ester, dipentaerythritol six (methyl) acrylate, three (methyl) acrylate of three (hydroxyethyl) isocyanuric acid esters etc. (methyl) acrylic monomer；Triallylcyanurate etc..Wherein, particularly preferred multifunctional (methyl) acrylate class.This (C) reactive diluent can be used alone a bit, can also be applied in combination two or more.
For the use level of (C) reactive diluent in colour filter resin combination of the invention, by the filter When color device is set as 100 mass parts with the summation of the ingredient other than (B) solvent in resin combination, preferably 5 mass parts ~85 mass parts, more preferably 15 mass parts~75 mass parts, most preferably 20 mass parts~65 mass parts.When (C) reactivity The use level of diluent within the above range when, the viscosity and photo-curable of colour filter resin combination become more appropriate.
[(D) Photoepolymerizationinitiater initiater]
As (D) Photoepolymerizationinitiater initiater being matched in colour filter resin combination of the invention, it is not particularly limited, Such as it can enumerate: the benzoins such as benzoin, benzoin methylether, benzoin ethyl ether and its alkyl ether；Acetophenone, 2,2- bis- Methoxyl group -2- phenyl acetophenone, 1,1- dichloroacetophenone, 4- (two oxygroup -1- Methylethyl of 1- tert-butyl) acetophenone Equal acetophenones；The alkyl phenones such as 1- hydroxycyclohexylphenylketone, 2- hydroxy-2-methyl -1- phenyl-propane -1- ketone Class；The Anthraquinones such as 2-methylanthraquinone, 2- amyl anthraquinone, 2- tert-butyl anthraquinone, 1- chloroanthraquinone；2,4- dimethyl thioxanthones, The thioxanthene ketone class such as 2,4- diisopropylthioxanthones, 2-chlorothioxanthone；The contracting such as acetophenone dimethyl ketal, benzyl dimethyl ketal Ketone；Benzophenone, 4- (two oxygroup -1- Methylethyl of 1- tert-butyl) benzophenone, 3,3 ', 4,4 '-four (tert-butyls Two Epoxide carbonyls) benzophenones such as benzophenone；1,2- octanedione, 1- [4- (thiophenyl) -2- (O- benzoyl Base oxime)], ethyl ketone, 1- [9- ethyl -6- (2- methyl benzoyl) -9H- carbazole -3- base], 1- (O- acetyl group Oxime) etc. oximes esters；2- methyl-1-[4- (methyl mercapto) phenyl]-2- morpholino-propane-1- ketone；2- benzyl- 2- dimethylamino -1- (4- morphlinophenyl) butanone -1；It is 2,4,6-trimethylbenzoyldiphenylphosphine oxide, double The acylphosphine oxide class such as (2,4,6- trimethylbenzoyl) phenyl phosphine oxide；Xanthene ketone etc..These (D) photopolymerization cause Agent can be used alone, and can also be applied in combination two or more.
For the use level of (D) Photoepolymerizationinitiater initiater in colour filter resin combination of the invention, by the filter When color device is set as 100 mass parts with the summation of the ingredient other than (B) solvent in resin combination, preferably 0.1 mass Part~30 mass parts, more preferably 0.5 mass parts~20 mass parts, most preferably 1 mass parts~15 mass parts.When (D) light is poly- When closing the use level of initiator within the above range, the photo-curable of colour filter resin combination becomes more appropriate.
[(E) colorant]
As (E) colorant being matched in colour filter resin combination of the invention, well known dyestuff can be used Or pigment.
In the case where using dyestuff as (E) colorant, compared with the case where using pigment, can obtain of high brightness Colored pattern, in addition, showing good alkali-developable.
As dyestuff, its in the dissolubility and colour filter resin combination from (B) solvent and alkaline-based developer The viewpoints such as interaction, the heat resistance of his ingredient consider acid dyes, acid dye, it is preferable to use with acidic-groups such as carboxyls Salt, the sulfonamide body of acid dyes etc. of material and nitrogen compound.As such dyestuff, for example, can enumerate: acid alizarine is purple N；Acid black 1,2,24,48；Blue VRS, 7,9,25,29,40,45,62,70,74,80,83,90,92,112,113,120, 129,147；Acid chrome violet K；Acid fuchsin；Acid green 1,3,5,25,27,50；Acid orange 6,7,8,10,12,50,51,52, 56,63,74,95；Azogeramine, 4,8,14,17,18,26,27,29,31,34,35,37,42,44,50,51,52,57,69, 73、80、87、88、91、92、94、97、103、111、114、129、133、134、138、143、145、150、151、158、176、 183,198,211,215,216,217,249,252,257,260,266,274；Acid violet 6B, 7,9,17,19；Indian yellow 1,3, 9,11,17,23,25,29,34,36,42,54,72,73,76,79,98,99,111,112,114,116；Food Huang 3 and it Derivative etc..Wherein, the preferred acid dyes of azo system, xanthene system, anthraquinone system or phthalocyanine system.These dyestuffs are according to mesh The color of mark pixel can be used alone, and can also be applied in combination two or more.
As pigment, for example, can enumerate: C.I. pigment yellow 1,3,12,13,14,15,16,17,20,24,31,53, 83、86、93、94、109、110、117、125、128、137、138、139、147、148、150、153、154、166、173、194、 214 equal yellow uitramarines；C.I. the orange face such as pigment orange 13,31,36,38,40,42,43,51,55,59,61,64,65,71,73 Material；C.I. Pigment Red 9,97,105,122,123,144,149,166,168,176,177,180,192,209,215,216, 224, the red pigments such as 242,254,255,264,265；C.I. the blue pigments such as pigment blue 15,15:3,15:4,15:6,60； C.I. the violet pigments such as pigment violet 1,19,23,29,32,36,38；C.I. the viridine greens such as pigment Green 7,36,58；C.I. pigment The brown pigments such as palm fibre 23,25；C.I. pigment black 1,7, carbon black, titanium is black, black pigments such as iron oxide etc..These pigment are according to target The color of pixel can be used alone, and can also be applied in combination two or more, and dyestuff and pigment also can be used together.
For the use level of (E) colorant in colour filter resin combination of the invention, used by the colour filter When the summation of the ingredient other than (B) solvent in resin combination is set as 100 mass parts, preferably 5 mass parts~75 matter Measure part, more preferably 5 mass parts~65 mass parts, most preferably 10 mass parts~55 mass parts.
In the case where using pigment as (E) colorant, from the viewpoint of the dispersibility for improving pigment, can filter Cooperate well known dispersing agent in color device resin combination.
As dispersing agent, it is preferable to use through when the excellent macromolecule dispersing agent of dispersion stabilization.Disperse as macromolecule Agent, for example, can enumerate: carbamate system dispersing agent, polyethylene imine system dispersing agent, polyoxyethylene ether system point Powder, polyoxyethylene glycol diester-based dispersing agent, Sorbitan fatty esters system dispersing agent, aliphatic modified ester system dispersant Deng.As such macromolecule dispersing agent, can be used with EFKA (EFKA chemicals BV (EFKA) corporation), (ZENECA is public by Disperbyk (Byk Chemie corporation), DISPARLON (this chemical conversion of nanmu Co. Ltd. system), SOLSPERSE Department system) etc. the commercially available substance of trade names.
Colour filter of the invention is carried out suitably with the use level of the dispersing agent in resin combination according to the type of pigment etc. Adjustment.
In colour filter resin combination of the invention, in addition to the above-mentioned components, in order to assign defined characteristic, Additive well known to well known coupling agent, levelling agent, hot polymerization inhibitor etc. can also be cooperated.This in colour filter resin combination The use level of a little additives is not particularly limited if in a range that does not hinder the effect of the present invention.
Colour filter of the invention with resin combination can be mixed by using well known mixing arrangement above-mentioned ingredient come Preparation, alternatively, can also be by after first preparing the composition containing (A) copolymer and (B) solvent, that is, make containing (A-1) monomer mixture of compound, (A-2) compound and (A-3) compound is copolymerized it in the presence of (B) solvent Afterwards, (C) reactive diluent, (D) Photoepolymerizationinitiater initiater and (E) colorant are added and is mixed to prepare.In the preparation of the latter In method, as needed, addition (B) solvent can also be added after copolymerization.
Colour filter of the invention has alkali-developable with resin combination, therefore can be carried out by using alkaline aqueous solution Development.In particular, to provide sensitivity, developability excellent for colour filter resin combination of the invention, and solvent resistance is excellent Different colored pattern.Therefore, colour filter of the invention is suitable as being embedded in organic EL for manufacturing and showing with resin combination Device, liquid crystal display device, solid-state image pickup element colour filter resist.
[colour filter]
Then, to using colour filter of the invention to be illustrated with the colour filter that resin combination is produced.
Colour filter of the invention has the colored pattern formed by above-mentioned colour filter resin combination.
Hereinafter, being illustrated referring to attached drawing to colour filter of the invention.
Fig. 1 is the summary section for indicating the colour filter of one embodiment of the present invention.
As shown in Figure 1, colour filter of the invention has: substrate 1；Black matrix" 3 is formed in the one side of substrate 1, is formed In the pixel 2 of RGB and the boundary of pixel 2；And protective film 4, it is formed on pixel 2 and black matrix" 3.
For colour filter of the invention, in addition to pixel 2 and black matrix" 3 (colored pattern) use above-mentioned colour filter Except device is formed with resin combination, other compositions can use well known composition.
It should be noted that the composition of colour filter shown in Fig. 1 is an example, colour filter of the invention is not merely It is defined in this composition.
Then, the manufacturing method of colour filter of the invention is illustrated.
Firstly, the one side in substrate 1 forms colored pattern.Specifically, substrate 1 sequentially form on one side pixel 2 with And black matrix" 3.
It as substrate 1, is not particularly limited, can enumerate: glass substrate, silicon substrate, polycarbonate substrate, polyester base Plate, polyamide substrate, polyamideimide-based plate, polyimide substrate, aluminum substrate, printed circuit board, array substrate etc..
Colored pattern can be formed by photoetching process.Specifically, being used in the above-mentioned colour filter of the coated on one side of substrate 1 Resin combination is simultaneously formed after coated film, across the photomask of predetermined pattern, is exposed to coated film and is made exposed portion Photocuring.Then, it after being developed using alkaline aqueous solution to unexposed portion, is toasted, as defined in being formed Colored pattern.
It as the coating method of colour filter resin combination, is not particularly limited, can be used: silk screen print method, roller coating Method, curtain coating processes, spray coating method, spin-coating method, slot coated method etc..
Furthermore it is possible to which as needed, use is circulating in coating colour filter resin combination and after forming coated film The heating units such as baking oven, infrared heater, hot plate (hot plate), heat coated film, thus wave (B) solvent Hair.
Heating condition is not particularly limited, and is suitably set according to the composition of colour filter resin combination.For example, will coating Film 50 DEG C~120 DEG C at a temperature of heat 30 seconds~30 minutes.
As for not limiting especially to the light source being exposed by colour filter with the coated film that resin combination is formed It is fixed, such as can be used: low pressure mercury lamp, medium pressure mercury lamp, high-pressure sodium lamp, xenon lamp, metal halide lamp etc..In addition, light exposure is also simultaneously It is not particularly limited, is suitably set according to the composition of colour filter resin combination.
It as the alkaline aqueous solution for development, is not particularly limited, such as can be used: sodium carbonate, potassium carbonate, carbonic acid The aqueous solution of calcium, sodium hydroxide, potassium hydroxide etc.；The aqueous solution of the amine compounds such as ethamine, diethylamine, dimethylethanolamine； The aqueous solution of the quaternary ammonium salts such as tetramethyl ammonium hydroxide；3- methyl -4- amino-N, N- diethylaniline, 3- methyl -4- Amino-N- ethyl-N- beta-hydroxy ethyl aniline, 3- methyl -4- amino-N- ethyl-N- β-Methanesulfomide second Base aniline, 3- methyl -4- amino-N- ethyl-N- 'beta '-methoxy ethyl aniline and their sulfate, hydrochloride Or the aqueous solution etc. of the p-phenylenediamine based compound such as tosilate.Wherein, it is preferable to use p-phenylenediamine based compound Aqueous solution.It should be noted that in these alkaline aqueous solutions as needed, defoaming agent, surfactant can be added.Separately Outside, it preferably after being developed by above-mentioned alkaline aqueous solution, washes and makes it dry.
The condition of baking is not particularly limited, and is heated according to the composition of colour filter resin combination. For example, 130 DEG C~250 DEG C at a temperature of heat 10 minutes~60 minutes.
By using colour filter resin combination and repeat coating, exposure, development and baking as described above, Desired pixel 2 and black matrix" 3 (colored pattern) can be sequentially formed.
It should be noted that in the present embodiment, being carried out to the forming method for the colored pattern realized by photocuring Explanation, but the present invention is not limited to this.If replacing (D) using curing accelerator and well known epoxy resin has been cooperated The resin combination of Photoepolymerizationinitiater initiater can also then be heated after being coated with by ink-jet method, is consequently formed desired Colored pattern.
Then, protective film 4 is formed on colored pattern (pixel 2 and black matrix" 3).
Protective film 4 is not particularly limited, and well known material and forming method can be used to be formed.
For the colour filter manufactured in this way, due to using offer sensitivity, developability excellent, and solvent resistance is excellent The colour filter of different colored pattern is manufactured with resin combination, thus with excellent solvent resistance colored pattern (pixel 2 with And black matrix" 3).
[image-displaying member]
Image-displaying member of the invention has above-mentioned colour filter.As image-displaying member of the invention, if having Above-mentioned colour filter is then not particularly limited, such as can be enumerated: liquid crystal display element, organic EL display element etc..For this For the image-displaying member of invention, due to having above-mentioned colour filter, it is able to achieve and is highlighted.
Embodiment
Hereinafter, by embodiment and comparative example, more specifically the present invention will be described, but the present invention does not limit In embodiment below.
It should be noted that silylation equivalent is divided by the silane in each molecule in embodiment and comparative example The molecular weight of (A) copolymer after the mean number of base is the calculated calculated value of charge weight based on (A-2) compound.
The synthesis example of (A) copolymer described below.
[synthesis example 1]
Into the flask for having agitating device, dropping funel, condenser, thermometer and gas introduction tube, it is added the third two Alcohol monomethyl ether 700.0g is stirred while carrying out nitrogen displacement, is warming up to 88 DEG C.
Then, methacrylic acid 46.2g (0.54 mole), 3- methacryloxypropyl trimethoxy will contained 2 are added in the monomer mixture of silane 60.5g (0.24 mole) and methyl methacrylate 166.0g (1.66 moles), Substance obtained by 2 '-azo two (isobutyric acid) dimethyl ester (polymerization initiator) 27.3g, is added dropwise to the flask from dropping funel In.
After completion of dropwise addition, 5 hours are stirred at 88 DEG C to carry out copolyreaction, obtained sample 1 (weight average molecular weight: 7100, molecular weight distribution (Mw/Mn): 2.1, acid value: 99KOHmg/g, silylation equivalent: 1230g/mol).
[synthesis example 2~6 compares synthesis example 1~5]
Other than using raw material documented by table 1 and table 2, in the same manner as synthesis example 1, copolyreaction is carried out, is obtained Sample 2~11.The weight average molecular weight of resulting sample, molecular weight distribution (Mw/Mn), acid value and silylation equivalent are shown in Table 1 and table 2.In addition, (A-1) compound~(A-3) compound mole % that will be used to prepare (A) copolymer is shown in table 3。
[comparing synthesis example 6]
Into the flask for having agitating device, dropping funel, condenser, thermometer and gas introduction tube, it is packed into 2,2- 250 mass parts of 5 mass parts of azodiisobutyronitrile and acetic acid 3- methoxybutyl are further packed into 18 mass of methacrylic acid Part, 25 mass parts of methacrylic acid tricyclic [5.2.1.02.6] decane -8- base, 5 mass parts of styrene, 3- acryloxy 32 mass parts of 20 mass parts of propyl trimethoxy silicane and 3- ethyl -3- methacryloxymethyl oxetanes And after carrying out nitrogen displacement, slowly it is stirred, and the temperature of solution is made to rise to 80 DEG C.After 1 hour, mixing Gelation occurs for solution, can not make sample well.
[table 1]
[table 2]
[table 3]
Using resulting sample 1~11, prepare as follows colour filter resin combination (dye-type) with And colour filter is with resin combination (color type).
The preparation > of < colour filter resin combination (dye-type)
According to gradation composition shown in table 4 and mixing ratio, prepares and used dyestuff (VALIFAST BLUE 2620) as the colour filter of (E) colorant with resin combination (colour resist).
It should be noted that the use level of (A) copolymer in table 4 used when not being included in synthesis (A) copolymer it is molten Agent, the use level of (B) solvent in table 4 are the propylene glycol lists of the solvent that will be used in synthesis (A) copolymer and additional cooperation The worthwhile value out of methyl ether.
[table 4]
The preparation > of < colour filter resin combination (color type)
Into the stainless steel vessel of 180 mass parts of zirconium oxide bead filled with diameter 0.5mm, 10 mass parts of investment C.I pigment green 36, the propylene glycol methyl ether acetate of 33.75 mass parts, 6.25 mass parts dispersing agent (trade name: Disperbyk-161, BYK Chemie Japan corporation), with paint shaker (paint shaker) mix 3 hours and Make its dispersion, thus prepares viridine green dispersion liquid.
According to gradation composition shown in table 5 and mixing ratio, prepares and used the viridine green dispersion liquid as (E) The colour filter of colorant is with resin combination (colour resist).
It should be noted that the use level of (A) copolymer in table 5 used when not being included in synthesis (A) copolymer it is molten Agent, the use level of (B) solvent in table 5 are the propylene glycol lists of the solvent that will be used in synthesis (A) copolymer and additional cooperation The worthwhile value out of methyl ether.
[table 5]
The evaluation > of < colour resist
(1) alkali-developable
Prepared colour filter is spun on the glass substrate (alkali-free glass substrate) of 5cm square with resin combination, So that after exposure with a thickness of after 2.5 μm, heated 3 minutes at 90 DEG C and solvent made to volatilize, formd on the glass substrate Coated film.
Then, the photomask that predetermined pattern is configured at the distance away from 100 μm of coated film, across the photomask, to coating Film is exposed (light exposure 150mJ/cm2), make exposed portion photocuring.
Then, the aqueous solution of the sodium carbonate containing 0.1 mass % is sprayed at 23 DEG C of temperature and pressure 0.3MPa, thus After unexposed portion dissolution is developed, confirmed by residue and development form.
It is aobvious that residue after alkali development observes alkali by using the electron microscope S-3400 of high and new technology company, Hitachi The pattern of movie queen is confirmed.The benchmark of the evaluation is as follows.
Zero: without residue
×: there is residue
By above-mentioned alkali-developable evaluation result is shown in table 6.
(2) solvent resistance
Prepared colour filter is spun on the glass substrate (alkali-free glass substrate) of 5cm square with resin combination, So that after baking with a thickness of after 2.5 μm, heated 3 minutes at 90 DEG C and solvent made to volatilize, formd on the glass substrate Coated film.
Then, coated film is exposed using the light of wavelength 365nm, after making exposed portion photocuring, in baking temperature It is placed 30 minutes in the drier of 230 DEG C of degree, produces cured coating film.
The n-methyl-2-pyrrolidone of 200mL is added in the vial with cover of capacity 500mL, in 60 DEG C of condition Under stood.After test film with above-mentioned cured coating film is impregnated in wherein, in the shape for being maintained predetermined temperature Under state, 30 minutes have been stood.
Test film, which is determined, using spectrophotometer UV-1650PC (Shimadzu Seisakusho Ltd.'s system) is impregnated in N- methyl -2- Color change (Δ E before and after pyrrolidones*ab).Δ E before and after dipping*When the value of ab is 4.5 or less, it may be said that cured film Solvent resistance it is good.
By above-mentioned solvent resistance evaluation result is shown in table 6.
[table 6]
It should be noted that, as additive, being added to CPI in the embodiment 6 and embodiment 12 in above-mentioned table 6 (registered trademark) -100P (SAN-APRO corporation, photoacid generator).The additive amount of CPI (registered trademark) -100P relative to (A) 00 mass parts of copolymer 1 are set as 1 mass parts.
According to the result of table 6, it is known that: in the case where having used dyestuff as (E) colorant, use in synthesis example 1 The colour resist (Examples 1 to 6) of (A) copolymer obtained in~6 provides alkali-developable and excellent solvent resistance Pattern.
In contrast, having used the comparison synthesis example 1 of the hydroxyl solvent of unused carbon atom number 3~10 and having compared conjunction Solvent resistance at the colour resist (comparative example 1 and comparative example 2) of (A) copolymer of example 2 is insufficient, has used and has compared conjunction Alkali-developable at the colour resist (comparative example 1) of (A) copolymer of example 1 is also insufficient.In addition, having used (A-1) chemical combination The containing ratio of (A-2) compound in object~(A-3) compound is (A) copolymer of the comparison synthesis example 3 of 55 moles of % Colour resist (comparative example 3) alkali-developable it is good, but solvent resistance is insufficient.It has used without containing (A-1) compound Comparison synthesis example 4 (A) copolymer colour resist (comparative example 4) solvent resistance it is good, but alkali-developable is insufficient. The alkali development of the colour resist (comparative example 5) of (A) copolymer of the comparison synthesis example 5 without containing (A-2) compound is used Property is good, but solvent resistance is insufficient.
In the case where having used pigment as (E) colorant, use the colour of (A) copolymer of synthesis example 1~6 anti- Erosion agent (embodiment 7~12) provides the pattern of alkali-developable and excellent solvent resistance.
In contrast, having used the comparison synthesis example 1 of the hydroxyl solvent of unused carbon atom number 3~10 and having compared conjunction Solvent resistance at the colour resist (comparative example 6 and comparative example 7) of (A) copolymer of example 2 is insufficient, has used and has compared conjunction Alkali-developable at the colour resist (comparative example 6) of (A) copolymer of example 1 is also insufficient.In addition, having used (A-1) chemical combination The containing ratio of (A-2) compound in object~(A-3) compound is (A) copolymer of the comparison synthesis example 3 of 55 moles of % Colour resist (comparative example 8) alkali-developable it is good, but solvent resistance is insufficient.It has used without containing (A-1) compound Comparison synthesis example 4 (A) copolymer colour resist (comparative example 9) solvent resistance it is good, but alkali-developable is insufficient. Use the alkali of the colour resist (comparative example 10) of (A) copolymer of the comparison synthesis example 5 without containing (A-2) compound aobvious Shadow is good, but solvent resistance is insufficient.
Industrial availability
The present invention can provide it is a kind of provide be used as photosensitive material when, sensitivity, developability are good, and solvent resistance The colour filter resin combination of excellent colored pattern.In addition, the present invention can provide it is a kind of with excellent solvent resistance The colour filter of colored pattern.In addition, colour filter of the invention is high brightness, and high reliablity, therefore be suitable as being embedded in organic EL display device, liquid crystal display device, solid-state image pickup element colour filter.
Description of symbols
1: substrate；2: pixel；3: black matrix"；4: protective film.

Claims (5)

1. a kind of colour filter resin combination, which is characterized in that contain:
(A) copolymer contains structural unit (a-1), the following formula (1) for being originated from the polymerizable unsaturated compound with acidic group Shown in structural unit (a-2) and the structural unit (a-3) from other polymerizable unsaturated compounds, by whole knots When structure unit total is set as 100 moles of %, the structural unit (a-2) containing 1 mole of %~50 mole %, weight average molecular weight For 1000~50000 and molecular weight distribution (Mw/Mn) is 1.5~3.0；
(B) solvent, the hydroxyl solvent containing carbon atom number 3~10；
(C) reactive diluent；
(D) Photoepolymerizationinitiater initiater；And
(E) colorant,
In formula (1), R1Indicate hydrogen atom or methyl, R2~R4Each independently represent the alkyl of hydrogen atom, carbon atom number 1~6 Or the alkoxy of carbon atom number 1~6, n are the integer in 1~10, wherein R2~R4At least one of for carbon atom number 1~ 6 alkoxy.
2. colour filter resin combination according to claim 1, wherein
The acidic group of the structural unit (a-1) is carboxyl, and (A) copolymer contains the described of 10 moles of %~50 mole % Structural unit (a-1), and the acid value of (A) copolymer is 20KOHmg/g~300KOHmg/g.
3. colour filter resin combination according to claim 1 or 2, wherein
When the summation of the ingredient other than (B) solvent is set as 100 mass parts, the content of (A) copolymer is 5 The content of mass parts~85 mass parts, (C) reactive diluent is 5 mass parts~85 mass parts, and (D) photopolymerization is drawn The content for sending out agent is 0.1 mass parts~30 mass parts, and the content of (E) colorant is 5 mass parts~75 mass parts.
4. a kind of colour filter, which is characterized in that have by colour filter resin combination according to any one of claims 1 to 3 The colored pattern that object is formed.
5. a kind of manufacturing method of colour filter resin combination, which is characterized in that
It include: to make chemical combination shown in the polymerizable unsaturated compound that there is acidic group containing (A-1), (A-2) following formula (2) The monomer mixture of other polymerizable unsaturated compounds of object and (A-3), after being copolymerized in the presence of (B) solvent, addition (C) reactive diluent, (D) Photoepolymerizationinitiater initiater and (E) colorant and mixed process,
Wherein, when (A-1) compound, (A-2) compound and (A-3) compound total is set as 100 moles of %, Monomer mixture contains (A-2) compound of 1 mole of %~50 mole %, and (B) solvent contains carbon atom number 3~10 Hydroxyl solvent,
In formula (2), R1Indicate hydrogen atom or methyl, R2~R4Each independently represent the alkyl of hydrogen atom, carbon atom number 1~6 Or the alkoxy of carbon atom number 1~6, n are the integer in 1~10, wherein R2~R4At least one of for carbon atom number 1~ 6 alkoxy.
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