WO2018110097A1 - カラーフィルター用樹脂組成物、その製造方法及びカラーフィルター - Google Patents
カラーフィルター用樹脂組成物、その製造方法及びカラーフィルター Download PDFInfo
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- WO2018110097A1 WO2018110097A1 PCT/JP2017/038495 JP2017038495W WO2018110097A1 WO 2018110097 A1 WO2018110097 A1 WO 2018110097A1 JP 2017038495 W JP2017038495 W JP 2017038495W WO 2018110097 A1 WO2018110097 A1 WO 2018110097A1
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- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- MVQLEZWPIWKLBY-UHFFFAOYSA-N tert-butyl 2-benzoylbenzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 MVQLEZWPIWKLBY-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- JOHIXGUTSXXADV-UHFFFAOYSA-N undec-2-ene Chemical compound CCCCCCCCC=CC JOHIXGUTSXXADV-UHFFFAOYSA-N 0.000 description 1
- SDTYFWAQLSIEBH-UHFFFAOYSA-N undec-3-ene Chemical compound CCCCCCCC=CCC SDTYFWAQLSIEBH-UHFFFAOYSA-N 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
- 150000007964 xanthones Chemical class 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000002256 xylenyl group Chemical class C1(C(C=CC=C1)C)(C)* 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
Images
Classifications
-
- 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
Definitions
- the present invention relates to a resin composition for a color filter, a production method thereof, and a color filter.
- photosensitive resin compositions that can be cured by active energy rays such as ultraviolet rays and electron beams have been widely used in the fields of various coatings, printing, paints, adhesives and the like from the viewpoint of resource saving and energy saving. Also in the field of electronic materials such as printed wiring boards, photosensitive resin compositions curable with active energy rays are used for solder resists, color filter resists, and the like.
- the color filter generally includes a transparent substrate such as a glass substrate, red (R), green (G), and blue (B) pixels formed on the transparent substrate, a black matrix formed at the pixel boundary, It consists of a pixel and a protective film formed on the black matrix.
- the color filter having such a configuration is usually manufactured by sequentially forming a black matrix, a pixel, and a protective film on a transparent substrate.
- Various methods are disclosed as a method for forming a pixel and a black matrix (hereinafter, the pixel and the black matrix are referred to as a “colored pattern”).
- Examples of the method for forming a colored pattern include a pigment / dye dispersion method including a photolithography method in which a photosensitive resin composition is used as a resist and coating, exposure, development and baking of the photosensitive resin composition are repeated.
- This pigment / dye dispersion method is widely used at present because it has excellent durability such as light resistance and heat resistance and can form a colored pattern with few defects such as pinholes.
- the photosensitive resin composition used for the photolithographic method contains an alkali-soluble resin, a reactive diluent, a photopolymerization initiator, a colorant, and a solvent. While the pigment / dye dispersion method has the above-mentioned advantages, the pattern of each pixel of black matrix, R, G, and B is repeatedly formed. Degradability and heat-resistant yellowing are required. As new materials that meet this demand, the present inventors have derived from alkylene oxides represented by alicyclic monomers and ethoxylated o-phenylphenol (meth) acrylates (ie, 2-phenylphenoxyethyl (meth) acrylate). A copolymer of (meth) acrylate having a structure and an aryl residue has been proposed (see, for example, Patent Document 1).
- a liquid crystal display device is manufactured by sandwiching liquid crystal between a separately produced color filter substrate and a TFT (Thin-Film-Transistor) substrate and bonding these members together.
- the color filter substrate is provided with an alignment film such as a polyimide film in order to align the liquid crystal.
- NMP N-methylpyrrolidone
- the coloring material in the pixel has become a dye and the content concentration has been increased for further enhancement of brightness and color.
- dyes have higher solubility in solvents than pigments, and there is a problem that the dyes are eluted in the solvent exposed during the process and the chromaticity of the pixels changes. There is a need for improved sex.
- the condition may be 40 ° C. or higher, and the NMP resistance evaluation test of the color filter is also performed at high temperature (50 ° C. or higher).
- a method for improving solvent resistance using a copolymer having an epoxy group or oxetanyl group and a carboxyl group or a phenolic hydroxyl group see, for example, Patent Documents 2 and 3 or a trihalomethyl group as a polymerization initiator.
- a method for improving the solvent resistance using a molecule containing a molecule having an oxadiazole structure or a triazine structure has been proposed, but these have insufficient solvent resistance.
- the present invention has been made to solve the above-described problems, and provides a resin composition for a color filter that has a good sensitivity and developability and gives a colored pattern with excellent solvent resistance. With the goal. Moreover, it aims at providing the color filter which has a coloring pattern excellent in solvent resistance.
- the present inventors have determined that a resin composition containing a specific copolymer, a specific solvent, a reactive diluent, a photopolymerization initiator, and a colorant.
- the present inventors have found that the above problems can be solved, and have completed the present invention.
- A Structural unit (a-1) derived from a polymerizable unsaturated compound having an acid group, structural unit (a-2) represented by the following formula (1), and other polymerizable unsaturated compound A copolymer containing 1 to 50 mol% of
- R 1 represents a hydrogen atom or a methyl group
- R 2 to R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
- N is an integer of 1 to 10, provided that at least one of R 2 to R 4 is an alkoxy group having 1 to 6 carbon atoms.
- the acid group of the structural unit (a-1) is a carboxyl group
- the copolymer (A) contains 10 to 50 mol% of the structural unit (a-1)
- the content of the copolymer (A) is 5 parts by mass to 85 parts by mass
- the reactive diluent (C) The content is 5 to 85 parts by mass
- the content of the (D) photopolymerization initiator is 0.1 to 30 parts by mass
- the content of the (E) colorant is 5 to 75 parts by mass.
- a monomer mixture comprising (A-1) a polymerizable unsaturated compound having an acid group, (A-2) a compound represented by the following formula (2), and (A-3) another polymerizable unsaturated compound.
- (B) a resin for color filter comprising a step of copolymerizing in the presence of a solvent and then adding and mixing (C) a reactive diluent, (D) a photopolymerization initiator and (E) a colorant
- a method for producing a composition comprising: When the total of (A-1) compound, (A-2) compound and (A-3) compound is 100 mol%, the monomer mixture contains 1 mol% to 50 mol% of (A-2) compound, And (B) a method for producing a resin composition for a color filter, wherein the solvent contains a hydroxy group-containing solvent having 3 to 10 carbon atoms.
- R 1 represents a hydrogen atom or a methyl group
- R 2 to R 4 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
- N is an integer of 1 to 10, provided that at least one of R 2 to R 4 is an alkoxy group having 1 to 6 carbon atoms.
- the present invention it is possible to provide a resin composition for a color filter that has a good sensitivity and developability and gives a colored pattern excellent in solvent resistance. Moreover, according to this invention, the color filter which has a coloring pattern excellent in solvent resistance can be provided.
- the resin composition for a color filter of the present invention comprises (A) a copolymer, (B) a solvent, (C) a reactive diluent, (D) a photopolymerization initiator, and (E) a colorant. It contains.
- the copolymer (A) in the present invention includes a structural unit (a-1) derived from a polymerizable unsaturated compound having an acid group, and the following formula (1):
- R 1 represents a hydrogen atom or a methyl group
- R 2 to R 4 each independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
- N is an integer of 1 to 10, provided that at least one of R 2 to R 4 is an alkoxy group having 1 to 6 carbon atoms) (a-2)
- a structural unit (a-3) derived from another polymerizable unsaturated compound.
- the copolymer (A) in the present invention has the structural unit (a-) when the total of the structural unit (a-1), the structural unit (a-2) and the structural unit (a-3) is 100 mol%. 2) is contained in an amount of 1 mol% to 50 mol%.
- the content ratio of the structural unit (a-2) is preferably 5 mol% to 40 mol%, more preferably 10 mol% to 30 mol%.
- the copolymer (A) in the present invention preferably contains 10 to 50 mol%, more preferably 15 to 45 mol%, most preferably 20 mol of the structural unit (a-1).
- the copolymer (A) preferably contains 1 to 89 mol%, more preferably 15 to 80 mol%, most preferably 30 mol of the structural unit (a-3). % To 70 mol%. When the content ratio of the structural unit (a-3) is within the above range, better developability and solvent resistance can be obtained.
- the weight average molecular weight (Mw) of the copolymer (A) is 1000 to 50000, preferably 2000 to 40000, more preferably 3000 to 30000 in terms of polystyrene.
- Mw weight average molecular weight
- the value of the weight average molecular weight (Mw) of the (A) copolymer in the present invention is measured under the following conditions using gel permeation chromatography (GPC) and is calculated in terms of polystyrene.
- the molecular weight distribution (Mw / Mn) of the copolymer (A) is 1.5 to 3.0, preferably 1.5 to 2.8, more preferably 1.5 to 2. 6.
- the molecular weight distribution (Mw / Mn) of the copolymer (A) exceeds 3.0, the developability varies. Mw / Mn is measured from the chromatogram of the GPC measurement.
- the acid value of the (A) copolymer in the present invention is not particularly limited, but is preferably 20 KOH mg / g to 300 KOH mg / g, more preferably 30 KOH mg / g to 200 KOH mg / g. If the acid value of (A) copolymer is 20 KOHmg / g or more, better developability can be obtained. On the other hand, if the acid value of the (A) copolymer is 300 KOH mg / g or less, the exposed portion (photocured portion) is not dissolved in the alkali developer.
- the acid value of (A) copolymer is a value measured using a mixed indicator of bromothymol blue and phenol red according to JIS K6901 5.3, and is included in 1 g of (A) copolymer. Means the number of mg of potassium hydroxide required to neutralize the acidic component.
- the unsaturated group equivalent is not particularly limited, but is preferably 100 g / mol to 4000 g / mol, more preferably 200 g / mol to 3000 g / mol. is there.
- the unsaturated group equivalent of a copolymer is 100 g / mol or more, it is effective in improving heat-resistant decomposability and heat-resistant yellowing.
- the unsaturated group equivalent of the copolymer (A) is 4000 g / mol or less, it is effective to further increase the sensitivity.
- the silyl group equivalent of the (A) copolymer in the present invention is not particularly limited, but is preferably 400 g / mol to 4000 g / mol, more preferably 500 g / mol to 3000 g / mol.
- (A) If the silyl group equivalent of a copolymer is 400 g / mol or more, it is effective in improving heat-resistant decomposability and heat-resistant yellowing. On the other hand, when the silyl group equivalent of the copolymer (A) is 4000 g / mol or less, it is effective to further improve the solvent resistance.
- the silyl group equivalent of (A) copolymer is the molecular weight of (A) copolymer divided by the average number of silyl groups per molecule, and is based on the charged amount of compound (A-2) described later. Calculated value.
- the above-mentioned copolymer (A) includes (B) a polymerizable unsaturated compound having an acid group (A-1) in the presence of a solvent containing a hydroxy group-containing solvent having 3 to 10 carbon atoms, (A- 2)
- A- 1 a polymerizable unsaturated compound having an acid group (A-1) in the presence of a solvent containing a hydroxy group-containing solvent having 3 to 10 carbon atoms
- R 1 represents a hydrogen atom or a methyl group
- R 2 to R 4 each independently represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or an alkoxy group having 1 to 6 carbon atoms.
- N is an integer of 1 to 10, provided that at least one of R 2 to R 4 is an alkoxy group having 1 to 6 carbon atoms
- a monomer mixture composed of another polymerizable unsaturated compound can be prepared by copolymerization according to a radical polymerization method known in the art.
- the compound (A-1), the compound (A-2) and the compound (A-3) are dissolved in the solvent (B) to prepare a solution, and a polymerization initiator is added to the solution.
- the reaction may be performed at ⁇ 130 ° C. for 1 hour to 20 hours.
- the number of repetitions of each compound and the order in which each compound binds in the copolymer are not particularly limited.
- the insufficient structural unit is converted into a copolymer by a modification reaction.
- a copolymer containing the structural unit (a-1), the structural unit (a-2) and the structural unit (a-3) may be prepared.
- the acid group of the polymerizable unsaturated compound having an acid group is not particularly limited, but usually a carboxyl group, a phosphoric acid group (—O—P ( ⁇ O) (OH) 2 ), a sulfonic acid group (—S ( ⁇ O) 2 OH) and the like are preferable.
- a carboxyl group is particularly preferable from the viewpoint of reactivity.
- the polymerizable unsaturated compound having an acid group is not particularly limited as long as it is a monomer having an acid group and an ethylenically unsaturated group.
- Specific examples of the compound (A-1) include, for example, (meth) acrylic acid, crotonic acid, cinnamic acid, vinyl sulfonic acid, 2- (meth) acryloyloxyethyl succinic acid, 2-acryloyloxyethyl phthalic acid, 2 -(Meth) acryloyloxyethyl hexahydrophthalic acid, 2- (meth) acryloyloxyethyl acid phosphate and the like.
- (meth) acrylic acid is preferable from the viewpoint of availability and reactivity.
- “(meth) acrylic acid” means at least one selected from methacrylic acid and acrylic acid. The same applies to “(meth) acrylate”.
- (A-2) Specific examples of the compound represented by the above formula (2) include, for example, 3- (meth) acryloyloxypropylmethyldimethoxysilane, 3- (meth) acryloyloxypropylethyldimethoxysilane, 3- (meth) Examples include meth) acryloyloxypropylmethyldiethoxysilane, 3- (meth) acryloyloxypropylethyldiethoxysilane, 3- (meth) acryloyloxypropyltrimethoxysilane, and 3- (meth) acryloyloxypropyltriethoxysilane. .
- 3- (meth) acryloyloxypropyltrimethoxysilane and 3- (meth) acryloyloxypropyltriethoxysilane are preferable from the viewpoint of availability and reactivity.
- the other polymerizable unsaturated compound is a polymerizable unsaturated compound other than the components (A-1) and (A-2), has no acid group or silyl group, and (A -1) A polymerizable unsaturated compound copolymerizable with the compound and the compound (A-2).
- polymerizable unsaturated compounds include, for example, dienes such as butadiene; methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) Acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, pentyl (meth) acrylate, neopentyl (meth) acrylate, benzyl (meth) Acrylate, isoamyl (meth) acrylate, hexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, benzyl (meth) acrylate, lauryl (meth) acrylate, dodecyl (meth) acrylate, cycl
- (3-ethyloxetane-3-yl) methyl (meth) acrylate, N, N-diethylaminoethyl (meth) acrylate, (meth) acrylic acid N, N-dimethylamide, (meth) acryl morpholine, styrene, vinyl Toluene and norbornene are preferred.
- Methyl (meth) acrylate, benzyl (meth) acrylate, dicyclopentanyl (meth) acrylate, glycidyl (meth) acrylate, (3-ethyloxetane-3-yl) methyl (meth) acrylate, styrene And vinyl Toluene is more preferable.
- These (A-3) compounds may be used alone or in combination of two or more.
- alkyl (meth) acrylate is preferable from the viewpoint of heat decomposition resistance and heat yellowing resistance, and methyl (meth) acrylate, benzyl (meth) acrylate, and dicyclopentanyl (meth) acrylate are more preferable.
- a polymerizable compound having a functional group that reacts with an acid group is preferable, and specifically, a polymerizable compound having a glycidyl group, an oxetanyl group, an isocyanato group, or a block isocyanato group can be mentioned. It is done. More preferred are glycidyl (meth) acrylate, (3-ethyloxetane-3-yl) methyl methacrylate and the like from the viewpoint of availability and reactivity.
- Examples of the blocking agent used for blocking the isocyanato group include lactams such as ⁇ -caprolactam, ⁇ -valerolactam, ⁇ -butyrolactam, ⁇ -propiolactam; methanol, ethanol, propanol, butanol, ethylene glycol, methyl Alcohols such as cellosolve, butyl cellosolve, methyl carbitol, benzyl alcohol, phenyl cellosolve, furfuryl alcohol, cyclohexanol; butylphenols such as phenol, cresol, xylenol, ethylphenol, o-isopropylphenol, p-tert-butylphenol, p- tert-octylphenol, nonylphenol, dinonylphenol, styrenated phenol, oxybenzoate, thymol, p-naphthol Phenols such as p-nitrophenol and p-
- the monomer mixture preferably contains 10 mol% to 50 mol%, more preferably 15 mol% to 45 mol% of the compound (A-1). , Most preferably 20 mol% to 40 mol%.
- the monomer mixture contains (A-2) 1 mol% to 50 mol%, preferably 5 mol% to 40 mol%, more preferably 10 mol% to 30 mol%.
- the monomer mixture contains 1 mol of the compound (A-3), preferably % To 89 mol%, more preferably 15 mol% to 80 mol%, and most preferably 30 mol% to 70 mol%.
- (A) While controlling the weight molecular weight and molecular weight distribution (Mw / Mn) of a copolymer to a predetermined range, and obtaining the coloring pattern which has desired solvent resistance, it uses for (B) solvent used for copolymerization reaction. Needs to contain a hydroxy group-containing solvent having 3 to 10 carbon atoms. When a copolymerization reaction is carried out using a solvent that does not contain a hydroxy group-containing solvent having 3 to 10 carbon atoms, gelation occurs or the weight molecular weight and molecular weight distribution (Mw / Mn) of the resulting copolymer are predetermined. Not within range.
- a solvent having one hydroxy group is preferable.
- the hydroxy group-containing solvent having 3 to 10 carbon atoms include, for example, monoalcohols such as propyl alcohol, butyl alcohol, pentyl alcohol, hexyl alcohol, octyl alcohol, nonyl alcohol, decyl alcohol, dodecyl alcohol, and benzyl alcohol.
- Ethylene glycol monomethyl ether Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene Glycol monomethyl ether, propylene glycol monoethyl ether Ter, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether, etc.
- Alkylene glycol monoalkyl ethers and the like Alkylene glycol monoalkyl ethers and the like.
- One of these hydroxy group-containing solvents having 3 to 10 carbon atoms may be used alone, or two or more thereof may be used in combination.
- the above-mentioned alcohol includes, for example, various isomers such that propyl alcohol includes 2-propyl alcohol in addition to 1-propyl alcohol.
- the solvent used for the copolymerization reaction may contain other solvents.
- Other solvents include, for example, (poly) alkylene glycol monoalkyl ether acetates such as ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate; diethylene glycol dimethyl ether, diethylene glycol Other ethers such as methyl ethyl ether, diethylene glycol diethyl ether and tetrahydrofuran; ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone and 3-heptanone; methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate, 2-hydroxy- Methyl 2-methylpropionate, 2-hydroxy-2-methyl Ethyl propionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionat
- the content ratio of the hydroxy group-containing solvent having 3 to 10 carbon atoms is preferably 10% by mass to 100% by mass and more preferably 20% by mass to 100% by mass with respect to the solvent (B) used in the copolymerization reaction. It is more preferable.
- the content ratio of the hydroxy group-containing solvent having 3 to 10 carbon atoms is within the above range, the weight molecular weight and molecular weight distribution (Mw / Mn) of the copolymer (A) can be easily controlled within a predetermined range, and the colored pattern The solvent resistance can be further improved.
- the amount of the (B) solvent used in the copolymerization reaction is not particularly limited.
- the amount is preferably 30 parts by mass to 1000 parts by mass, and more preferably 50 parts by mass to 800 parts by mass.
- the amount of the solvent used is 30 parts by mass or more, an abnormal polymerization reaction can be prevented and the polymerization reaction can be performed stably, and (A) the copolymer can be prevented from being colored or gelled.
- the polymerization initiator that can be used in this copolymerization reaction is not particularly limited, and examples thereof include 2,2′-azobis (isobutyronitrile) and 2,2′-azobis (2,4-dimethylvaleronitrile). ), 2,2′-azobis (isobutyric acid) dimethyl, benzoyl peroxide, t-butylperoxy-2-ethylhexanoate, and the like. These polymerization initiators may be used individually by 1 type, and may be used in combination of 2 or more type.
- the amount of the polymerization initiator used is not particularly limited, but is preferably 0 when the total amount of the (A-1) compound, (A-2) compound and (A-3) compound charged is 100 parts by mass. 0.5 to 20 parts by weight, more preferably 1.0 to 10 parts by weight.
- the blending amount of the (A) copolymer in the color filter resin composition of the present invention is preferably when the sum of the components excluding the solvent (B) in the color filter resin composition is 100 parts by mass.
- the amount is 5 to 85 parts by mass, more preferably 15 to 75 parts by mass, and most preferably 20 to 65 parts by mass.
- the curability of the color filter resin composition becomes more appropriate.
- the solvent used in the preparation of the copolymer (A) can be used as it is.
- a solvent can be further added. Moreover, when adding another component, the solvent which coexists there may be sufficient.
- the blending amount of the (B) solvent in the color filter resin composition of the present invention is preferably 30 masses when the total of the components excluding the (B) solvent in the color filter resin composition is 100 mass parts. Part to 1000 parts by weight, more preferably 50 parts by weight to 800 parts by weight, and most preferably 100 parts by weight to 700 parts by weight. (B) When the compounding quantity of a solvent exists in the said range, the viscosity of the resin composition for color filters will become more suitable.
- the (C) reactive diluent blended in the color filter resin composition of the present invention is not particularly limited, but those containing an ethylenically unsaturated double bond, a vinyl group, and a (meth) acryloyloxy group are preferred. .
- the reactive diluent (C) include aromatic vinyl monomers such as styrene, ⁇ -methylstyrene, ⁇ -chloromethylstyrene, vinyltoluene, divinylbenzene, diallylphthalate, diallylbenzenephosphonate; Polycarboxylic acid monomers such as vinyl and vinyl adipate; methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, ⁇ -hydroxyethyl (meth) acrylate, hydroxypropyl (meth ) Acrylate, ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, ethylene glycol di (meth) acrylate, trimethylolpropane di (meta) (Meth) acrylic monomers such as acrylate, trimethylolpropan
- the blending amount of the (C) reactive diluent in the color filter resin composition of the present invention is preferably when the sum of the components excluding the solvent (B) in the color filter resin composition is 100 parts by mass. Is 5 to 85 parts by mass, more preferably 15 to 75 parts by mass, and most preferably 20 to 65 parts by mass. (C) When the compounding quantity of a reactive diluent exists in the said range, the viscosity and photocurability of the resin composition for color filters will become more suitable.
- the photopolymerization initiator (D) blended in the color filter resin composition of the present invention is not particularly limited.
- benzoin such as benzoin, benzoin methyl ether, and benzoin ethyl ether and alkyl ethers thereof
- acetophenone Acetophenones such as 2,2-dimethoxy-2-phenylacetophenone, 1,1-dichloroacetophenone, 4- (1-t-butyldioxy-1-methylethyl) acetophenone
- anthraquinones such as 2-methylanthraquinone, 2-amylanthraquinone, 2-t-butylanthraquinone and 1-chloroanthraquinone
- the blending amount of the photopolymerization initiator (D) in the color filter resin composition of the present invention is preferably when the sum of the components excluding the solvent (B) in the color filter resin composition is 100 parts by mass. Is 0.1 to 30 parts by mass, more preferably 0.5 to 20 parts by mass, and most preferably 1 to 15 parts by mass. (D) When the compounding quantity of a photoinitiator is in the said range, the photocurability of the resin composition for color filters will become more suitable.
- (E) Colorant As the colorant (E) blended in the resin composition for a color filter of the present invention, a known dye or pigment can be used. (E) When a dye is used as the colorant, it is possible to obtain a colored pattern having a higher brightness than when a pigment is used, and it exhibits good alkali developability.
- Such dyes include, for example, acidacalizarinzviolet N; acid black1,2,24,48; acid blue1,7,9,25,29,40,45,62,70,74,80,83,90, 92, 112, 113, 120, 129, 147; acid chrome violetolK; acid Fuchsin; acidacgreen1, 3, 5, 25, 27, 50; acid range6, 7, 8, 10, 12, 50, 51, 52, 56, 63, 74, 95; acid red 1, 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, 13 , 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 ,
- pigments examples include C.I. 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, Yellow pigments such as 147, 148, 150, 153, 154, 166, 173, 194, 214; I. Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; I.
- Red pigments such as CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265; C. I. Blue pigments such as CI Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60; I. Violet pigments such as C.I. Pigment Violet 1, 19, 23, 29, 32, 36, 38; I. Green pigments such as CI Pigment Green 7, 36, 58; I. C.I. Brown pigments such as CI Pigment Brown 23 and 25; I. And black pigments such as CI pigment blacks 1 and 7, carbon black, titanium black, and iron oxide. These pigments may be used alone or in combination of two or more according to the target pixel color, or a dye and a pigment may be used in combination.
- the blending amount of the (E) colorant in the color filter resin composition of the present invention is preferably 5 when the sum of the components excluding the solvent (B) in the color filter resin composition is 100 parts by mass.
- the amount is from 75 to 75 parts by mass, more preferably from 5 to 65 parts by mass, and most preferably from 10 to 55 parts by mass.
- a known dispersant may be added to the color filter resin composition from the viewpoint of improving the dispersibility of the pigment.
- the dispersant it is preferable to use a polymer dispersant excellent in dispersion stability over time.
- the polymer dispersant include a urethane dispersant, a polyethyleneimine dispersant, a polyoxyethylene alkyl ether dispersant, a polyoxyethylene glycol diester dispersant, a sorbitan aliphatic ester dispersant, and an aliphatic modified ester. System dispersants and the like.
- Examples of such a polymer dispersing agent include EFKA (manufactured by EFKA Chemicals Beebuy (EFKA)), Disperbyk (manufactured by BYK Chemie), Disparon (manufactured by Enomoto Kasei Co., Ltd.), and SOLPERSE (manufactured by GENECA). You may use what is marketed.
- the blending amount of the dispersant in the resin composition for a color filter of the present invention is appropriately adjusted according to the type of pigment and the like.
- the color filter resin composition of the present invention is blended with known additives such as known coupling agents, leveling agents, thermal polymerization inhibitors, etc., in order to impart predetermined characteristics. May be.
- the compounding amount of these additives in the color filter resin composition is not particularly limited as long as the effects of the present invention are not impaired.
- the resin composition for a color filter of the present invention may be prepared by mixing the above components using a known mixing device, or previously contains (A) a copolymer and (B) a solvent. After preparing the composition, that is, after copolymerizing the monomer mixture comprising the compound (A-1), the compound (A-2) and the compound (A-3) in the presence of (B) a solvent, You may prepare by adding and mixing C) a reactive diluent, (D) a photoinitiator, and (E) a coloring agent. In the latter preparation method, the solvent (B) may be additionally added after the copolymerization, if necessary.
- the resin composition for a color filter of the present invention has alkali developability, it can be developed by using an alkaline aqueous solution.
- the color filter resin composition of the present invention is excellent in sensitivity and developability and can give a colored pattern excellent in solvent resistance. Therefore, the resin composition for a color filter of the present invention is suitably used as a resist used for producing a color filter incorporated in an organic EL display device, a liquid crystal display device, or a solid-state image sensor.
- FIG. 1 is a schematic cross-sectional view showing a color filter according to an embodiment of the present invention.
- the color filter of the present invention includes a substrate 1, a RGB matrix 2 formed on one surface of the substrate 1, a black matrix 3 formed at the boundary between the pixels 2, and a pixel 2. And a protective film 4 formed on the black matrix 3.
- the color filter of the present invention known configurations can be adopted for the other components except that the pixels 2 and the black matrix 3 (colored pattern) are formed using the above-described resin composition for a color filter. .
- the configuration of the color filter shown in FIG. 1 is an example, and the color filter of the present invention is not limited to this configuration.
- a colored pattern is formed on one surface of the substrate 1.
- the pixels 2 and the black matrix 3 are sequentially formed on one surface of the substrate 1.
- the base material 1 A glass substrate, a silicon substrate, a polycarbonate substrate, a polyester substrate, a polyamide substrate, a polyamideimide substrate, a polyimide substrate, an aluminum substrate, a printed wiring board, an array substrate etc. are mentioned.
- the colored pattern can be formed by a photolithography method. Specifically, after applying the above color filter resin composition on one surface of the substrate 1 to form a coating film, the coating film is exposed through a photomask having a predetermined pattern to expose an exposed portion. Is photocured. And a predetermined coloring pattern can be formed by baking after developing an unexposed part with aqueous alkali solution.
- the coating method of the color filter resin composition is not particularly limited, and screen printing, roll coating, curtain coating, spray coating, spin coating, slit coating, and the like are used.
- the coating film after forming the coating film by applying the color filter resin composition, if necessary, by heating the coating film using a heating means such as a circulation oven, an infrared heater, a hot plate, ( B)
- the solvent may be volatilized.
- the heating conditions are not particularly limited, and are appropriately set according to the composition of the color filter resin composition.
- the coating film may be heated at a temperature of 50 ° C. to 120 ° C. for 30 seconds to 30 minutes.
- the light source used for exposure of the coating film made of the resin composition for color filters is not particularly limited, and for example, a low pressure mercury lamp, a medium pressure mercury lamp, a high pressure mercury lamp, a xenon lamp, a metal halide lamp, or the like is used. Further, the exposure amount is not particularly limited, and is appropriately set according to the composition of the color filter resin composition.
- the aqueous alkali solution used for development is not particularly limited, but examples thereof include aqueous solutions of sodium carbonate, potassium carbonate, calcium carbonate, sodium hydroxide, potassium hydroxide, and the like; aqueous solutions of amine compounds such as ethylamine, diethylamine, dimethylethanolamine, and the like.
- an aqueous solution of a p-phenylenediamine compound such as p-toluenesulfonate Used.
- the baking conditions are not particularly limited, and heat treatment may be performed according to the composition of the color filter resin composition.
- the heating may be performed at a temperature of 130 ° C. to 250 ° C. for 10 minutes to 60 minutes.
- a desired pixel 2 and black matrix 3 can be sequentially formed by repeating the coating, exposure, development, and baking as described above using the resin composition for a color filter.
- this embodiment demonstrated the formation method of the coloring pattern by photocuring, this invention is not limited to this.
- D If the resin composition which mix
- the protective film 4 is formed on the colored pattern (pixel 2 and black matrix 3).
- the protective film 4 is not particularly limited, and is formed using a known material and a forming method.
- the color filter manufactured in this way is excellent in sensitivity and developability, and is manufactured using a resin composition for a color filter that gives a colored pattern excellent in solvent resistance. It has a coloring pattern (pixel 2 and black matrix 3).
- the image display element of the present invention includes the color filter described above.
- the image display element of the present invention is not particularly limited as long as it includes the color filter described above, and examples thereof include a liquid crystal display element and an organic EL display element. Since the image display element of the present invention includes the color filter described above, high-luminance display is possible.
- the silyl group equivalent is the molecular weight of the copolymer (A) divided by the average number of silyl groups per molecule, and is calculated based on the charged amount of the compound (A-2). Calculated value.
- a color filter resin composition (dye type) and a color filter resin composition (pigment type) were prepared according to the following method.
- the compounding quantity of (A) copolymer in Table 5 does not include the solvent used when synthesizing (A) copolymer, and the compounding quantity of (B) solvent in Table 5 is (A ) The sum of the solvent used in synthesizing the copolymer and propylene glycol monomethyl ether added additionally.
- the prepared resin composition for a color filter was spin-coated on a 5 cm square glass substrate (non-alkali glass substrate) so that the thickness after baking was 2.5 ⁇ m.
- the solvent was volatilized by heating at 0 ° C. for 3 minutes, and a coating film was formed on the glass substrate.
- the coating film was exposed to light having a wavelength of 365 nm and the exposed portion was photocured, and then left in a drier at a baking temperature of 230 ° C. for 30 minutes to prepare a cured coating film.
- 200 mL of N-methyl-2-pyrrolidone was placed in a 500 mL lidded glass bottle and allowed to stand at 60 ° C.
- CPI registered trademark
- -100P manufactured by San Apro, photoacid generator
- the color resists (Examples 7 to 12) using the copolymers (A) of Synthesis Examples 1 to 6 have patterns excellent in alkali developability and solvent resistance. Gave.
- the color resists (Comparative Examples 6 and 7) using the (A) copolymer of Comparative Synthesis Examples 1 and 2 that do not use a hydroxy group-containing solvent having 3 to 10 carbon atoms have solvent resistance.
- the color resist (Comparative Example 6) using the copolymer (A) of Comparative Synthesis Example 1 was not sufficient and the alkali developability was not sufficient.
- the present invention can provide a resin composition for a color filter which, when used as a photosensitive material, has a good sensitivity and developability and gives a colored pattern with excellent solvent resistance. Moreover, this invention can provide the color filter which has a coloring pattern excellent in solvent resistance.
- the color filter of the present invention is suitable as a color filter incorporated in an organic EL display device, a liquid crystal display device, and a solid-state image sensor because of high brightness and high reliability.
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Abstract
Description
顔料/染料分散法は、上記の利点を有している反面、ブラックマトリックス、R、G、Bの各画素のパターンを繰り返し形成することから、塗膜のバインダーとなるアルカリ可溶性樹脂には高い耐熱分解性と耐熱黄変性が要求される。この要求に応える新しい材料として、本発明者等は、脂環式モノマーとエトキシ化o-フェニルフェノール(メタ)アクリレート(すなわち、2-フェニルフェノキシエチル(メタ)アクリレート)に代表されるアルキレンオキシド由来の構造と、アリール残基とを有する(メタ)アクリレートの共重合体を提案している(例えば、特許文献1参照)。
また、カラーフィルターの色再現特性を向上させるために、配合する着色剤の含有量を多くしたり、膜厚を厚くしたりするなどの必要があるが、これらは同時に感度の低下、現像性の低下などの問題が生じる傾向にあり、更なる性能向上が求められている(例えば、特許文献5参照)。
[1](A)酸基を有する重合性不飽和化合物由来の構成単位(a-1)、下記式(1)で表される構成単位(a-2)並びに他の重合性不飽和化合物由来の構成単位(a-3)を含む共重合体であって、全構成単位の合計を100モル%としたときに構成単位(a-2)を1モル%~50モル%含み、重量平均分子量が1000~50000であり且つ分子量分布(Mw/Mn)が1.5~3.0である共重合体と、
(B)炭素原子数3~10のヒドロキシ基含有溶剤を含む溶剤と、
(C)反応性希釈剤と、
(D)光重合開始剤と、
(E)着色剤と
を含むことを特徴とするカラーフィルター用樹脂組成物。
[2]前記構成単位(a-1)の酸基がカルボキシル基であり、前記(A)共重合体が前記構成単位(a-1)を10モル%~50モル%含み、且つ前記(A)共重合体の酸価が20KOHmg/g~300KOHmg/gである[1]に記載のカラーフィルター用樹脂組成物。
[3]前記(B)溶剤を除く成分の総和を100質量部としたときに、前記(A)共重合体の含有量が5質量部~85質量部、前記(C)反応性希釈剤の含有量が5質量部~85質量部、前記(D)光重合開始剤の含有量が0.1質量部~30質量部、前記(E)着色剤の含有量が5質量部~75質量部である[1]又は[2]に記載のカラーフィルター用樹脂組成物。
[4][1]~[3]の何れかに記載のカラーフィルター用樹脂組成物から形成された着色パターンを有することを特徴とするカラーフィルター。
[5](A-1)酸基を有する重合性不飽和化合物、(A-2)下記式(2)で表される化合物並びに(A-3)他の重合性不飽和化合物からなるモノマー混合物を、(B)溶剤の存在下で共重合させた後、(C)反応性希釈剤、(D)光重合開始剤及び(E)着色剤を添加して混合する工程を含むカラーフィルター用樹脂組成物の製造方法であって、
(A-1)化合物、(A-2)化合物及び(A-3)化合物の合計を100モル%としたときにモノマー混合物が1モル%~50モル%の(A-2)化合物を含み、且つ(B)溶剤が炭素原子数3~10のヒドロキシ基含有溶剤を含むことを特徴とするカラーフィルター用樹脂組成物の製造方法。
本発明における(A)共重合体は、酸基を有する重合性不飽和化合物由来の構成単位(a-1)と、下記式(1):
カラム:ショウデックス(登録商標)LF-804+LF-804(昭和電工株式会社製)
カラム温度:40℃
試料:(A)共重合体の含有量が0.2質量%のテトラヒドロフラン溶液
展開溶媒:テトラヒドロフラン
検出器:示差屈折計(商品名:ショウデックス(登録商標)RI-71S、昭和電工株式会社製)
流速:1mL/min
なお、(A)共重合体の酸価とは、JIS K6901 5.3に従ってブロモチモールブルーとフェノールレッドの混合指示薬を用いて測定された値であって、(A)共重合体1g中に含まれる酸性成分を中和するのに要する水酸化カリウムのmg数を意味する。
なお、(A)共重合体のシリル基当量は、1分子当たりのシリル基の平均個数で割った(A)共重合体の分子量であり、後述の(A-2)化合物の仕込み量に基づいて算出される計算値とする。
(B)溶剤の使用量を30質量部以上とすることにより、異常な重合反応を防止し、重合反応を安定して行うことができるとともに、(A)共重合体の着色やゲル化を防止することもできる。また、(B)溶剤の使用量を1000質量部以下とすることにより、連鎖移動作用による(A)共重合体の分子量の低下を抑制し、且つ(A)共重合体の粘度を適切な範囲に制御することができる。
重合開始剤の使用量は、特に限定されないが、(A-1)化合物、(A-2)化合物及び(A-3)化合物の仕込み量の合計を100質量部としたときに、好ましくは0.5質量部~20質量部、より好ましくは1.0質量部~10質量部である。
本発明のカラーフィルター用樹脂組成物に配合される(B)溶剤は、上記した(A)共重合体を調製する際(共重合反応)に用いた溶剤をそのまま用いることができ、上記で例示した(B)溶剤をさらに加えることもできる。また、その他の成分を加える際に、そこに共存している溶剤であってもよい。
本発明のカラーフィルター用樹脂組成物に配合される(C)反応性希釈剤としては、特に限定されないが、エチレン性不飽和二重結合、ビニル基、(メタ)アクリロイルオキシ基を含むものが好ましい。(C)反応性希釈剤の具体例としては、例えば、スチレン、α-メチルスチレン、α-クロロメチルスチレン、ビニルトルエン、ジビニルベンゼン、ジアリルフタレート、ジアリルベンゼンホスホネート等の芳香族ビニル系モノマー類;酢酸ビニル、アジピン酸ビニル等のポリカルボン酸モノマー類;メチル(メタ)アクリレート、エチル(メタ)アクリレート、プロピル(メタ)アクリレート、ブチル(メタ)アクリレート、β-ヒドロキシエチル(メタ)アクリレート、ヒドロキシプロピル(メタ)アクリレート、エチレングリコールジ(メタ)アクリレート、ジエチレングリコールジ(メタ)アクリレート、プロピレングリコールジ(メタ)アクリレート、エチレングリコールジ(メタ)アクリレート、トリメチロールプロパンジ(メタ)アクリレート、トリメチロールプロパントリ(メタ)アクリレート、ペンタエリスリトールテトラ(メタ)アクリレート、ジペンタエリスリトールヘキサ(メタ)アクリレート、トリス(ヒドロキシエチル)イソシアヌレートのトリ(メタ)アクリレート等の(メタ)アクリル系モノマー;トリアリルシアヌレート等が挙げられる。これらの中でも、多官能(メタ)アクリレート類が特に好ましい。これらの(C)反応性希釈剤は、1種を単独で用いてもよいし、2種以上を組み合わせて用いてもよい。
本発明のカラーフィルター用樹脂組成物に配合される(D)光重合開始剤としては、特に限定されないが、例えば、ベンゾイン、ベンゾインメチルエーテル、ベンゾインエチルエーテル等のベンゾインとそのアルキルエーテル類;アセトフェノン、2,2-ジメトキシ-2-フェニルアセトフェノン、1,1-ジクロロアセトフェノン、4-(1-t-ブチルジオキシ-1-メチルエチル)アセトフェノン等のアセトフェノン類;1-ヒドロキシシクロヘキシルフェニルケトン、2-ヒドロキシ-2-メチル-1-フェニルプロパン-1-オン等のアルキルフェノン類;2-メチルアントラキノン、2-アミルアントラキノン、2-t-ブチルアントラキノン、1-クロロアントラキノン等のアントラキノン類;2,4-ジメチルチオキサントン、2,4-ジイソプロピルチオキサントン、2-クロロチオキサントン等のチオキサントン類;アセトフェノンジメチルケタール、ベンジルジメチルケタール等のケタール類;ベンゾフェノン、4-(1-t-ブチルジオキシ-1-メチルエチル)ベンゾフェノン、3,3’,4,4’-テトラキス(t-ブチルジオキシカルボニル)ベンゾフェノン等のベンゾフェノン類;1,2-オクタンジオン,1-[4-(フェニルチオ)-2-(O-ベンゾイルオキシム)]、エタノン,1-[9-エチル-6-(2-メチルベンゾイル)-9H-カルバゾール-3-イル],1-(0-アセチルオキシム)等のオキシムエステル類;2-メチル-1-[4-(メチルチオ)フェニル]-2-モルホリノ-プロパン-1-オン;2-ベンジル-2-ジメチルアミノ-1-(4-モルホリノフェニル)ブタノン-1;2,4,6-トリメチルベンゾイルジフェニルホスフィンオキサイド、ビス(2,4,6-トリメチルベンゾイル)フェニルホスフィンオキサイド等のアシルホスフィンオキサイド類;キサントン類等が挙げられる。これらの(D)光重合開始剤は、1種を単独で用いてもよいし、2種以上を組み合わせて用いてもよい。
本発明のカラーフィルター用樹脂組成物に配合される(E)着色剤としては、公知の染料又は顔料を用いることができる。
(E)着色剤として染料を用いる場合には、顔料を用いた場合に比べて、輝度の高い着色パターンを得ることができ、また、良好なアルカリ現像性を示す。
分散剤としては、経時の分散安定性に優れる高分子分散剤を用いることが好ましい。高分子分散剤としては、例えば、ウレタン系分散剤、ポリエチレンイミン系分散剤、ポリオキシエチレンアルキルエーテル系分散剤、ポリオキシエチレングリコールジエステル系分散剤、ソルビタン脂肪族エステル系分散剤、脂肪族変性エステル系分散剤等が挙げられる。このような高分子分散剤としては、EFKA(エフカーケミカルズビーブイ(EFKA)社製)、Disperbyk(ビックケミー社製)、ディスパロン(楠本化成株式会社製)、SOLSPERSE(ゼネカ社製)等の商品名で市販されているものを用いてもよい。
本発明のカラーフィルター用樹脂組成物における分散剤の配合量は、顔料等の種類に応じて適宜調整される。
次に、本発明のカラーフィルター用樹脂組成物を用いて作製されたカラーフィルターについて説明する。
本発明のカラーフィルターは、上述したカラーフィルター用樹脂組成物から形成された着色パターンを有する。
以下、図面を参照して、本発明のカラーフィルターについて説明する。
図1は、本発明の一実施形態のカラーフィルターを示す概略断面図である。
図1に示すように、本発明のカラーフィルターは、基板1と、基板1の一方の面上に形成される、RGBの画素2及び画素2の境界に形成されるブラックマトリックス3と、画素2及びブラックマトリックス3上に形成される保護膜4とを備える。
なお、図1に示したカラーフィルターの構成は一例であり、本発明のカラーフィルターは、この構成のみに限定されない。
まず、基材1の一方の面に着色パターンを形成する。具体的には、基材1の一方の面に、画素2及びブラックマトリックス3を順次形成する。
基材1としては、特に限定されないが、ガラス基板、シリコン基板、ポリカーボネート基板、ポリエステル基板、ポリアミド基板、ポリアミドイミド基板、ポリイミド基板、アルミニウム基板、プリント配線基板、アレイ基板等が挙げられる。
カラーフィルター用樹脂組成物の塗布方法としては、特に限定されないが、スクリーン印刷法、ロールコート法、カーテンコート法、スプレーコート法、スピンコート法、スリットコート法等が用いられる。
加熱条件は、特に限定されず、カラーフィルター用樹脂組成物の組成に応じて適宜設定される。例えば、塗布膜を、50℃~120℃の温度にて、30秒~30分加熱すればよい。
ベーキングの条件は、特に限定されず、カラーフィルター用樹脂組成物の組成に応じて加熱処理を行えばよい。例えば、130℃~250℃の温度にて、10分~60分間加熱すればよい。
なお、本実施形態では、光硬化による着色パターンの形成方法を説明したが、本発明はこれに限定されない。(D)光重合開始剤の代わりに、硬化促進剤及び公知のエポキシ樹脂を配合した樹脂組成物を用いれば、インクジェット法により塗布した後、加熱することにより、所望の着色パターンを形成することもできる。
保護膜4は、特に限定されず、公知の材料及び形成方法を用いて形成される。
本発明の画像表示素子は、上述したカラーフィルターを具備する。本発明の画像表示素子としては、上述したカラーフィルターを具備していれば特に限定されないが、例えば、液晶表示素子、有機EL表示素子等が挙げられる。本発明の画像表示素子は、上述したカラーフィルターを具備するため、高輝度表示が可能である。
攪拌装置、滴下ロート、コンデンサー、温度計及びガス導入管を備えたフラスコに、プロピレングリコールモノメチルエーテル700.0gを入れ、窒素置換しながら攪拌し、88℃に昇温した。
次に、メタクリル酸46.2g(0.54モル)、3-メタクリロイルオキシプロピルトリメトキシシラン60.5g(0.24モル)及びメチルメタクリレート166.0g(1.66モル)からなるモノマー混合物に、2,2’-アゾビス(イソ酪酸)ジメチル(重合開始剤)27.3gを添加したものを、滴下ロートから前記フラスコ中に滴下した。
滴下終了後、88℃にて5時間攪拌して共重合反応を行い、試料1(重量平均分子量:7100、分子量分布(Mw/Mn):2.1、酸価:99KOHmg/g、シリル基当量:1230g/mol)を得た。
表1及び2に記載の原料を用いる以外は合成例1と同様にして、共重合反応を行い、試料2~11を得た。得られた試料の重量平均分子量、分子量分布(Mw/Mn)、酸価及びシリル基当量を、表1及び2に示す。また、(A)共重合体を調製するのに用いた(A-1)化合物~(A-3)化合物のモル%を表3に示す。
攪拌装置、滴下ロート、コンデンサー、温度計及びガス導入管を備えたフラスコに、2,2-アゾビスイソブチロニトリル5質量部及び酢酸3-メトキシブチル250質量部を仕込み、さらにメタクリル酸18質量部、メタクリル酸トリシクロ[5.2.1.02.6]デカン-8-イル25質量部、スチレン5質量部、3-アクリオキシプロピロトリメトキシシラン20質量部、及び3-エチル-3-メタクリロイルオキシメチルオキセタン32質量部を仕込んで窒素置換した後、緩やかに撹拌しつつ、溶液の温度を80℃に上昇した。1時間経過後、混合溶液がゲル化し、良好に試料を作製することができなかった。
表4に示す配合成分及び配合割合に従って、(E)着色剤として、染料(VALIFAST BLUE 2620)を用いたカラーフィルター用樹脂組成物(カラーレジスト)を調製した。
なお、表4における(A)共重合体の配合量は、(A)共重合体を合成する際に用いた溶剤を含んでおらず、表4における(B)溶剤の配合量は、(A)共重合体を合成する際に用いた溶剤と追加で配合したプロピレングリコールモノメチルエーテルとを合算したものである。
直径0.5mmのジルコニアビーズ180質量部を充填したステンレス製容器に、C.Iピグメントグリーン36を10質量部、プロピレングリコールモノメチルエーテルアセテートを33.75質量部、分散剤(商品名:Disperbyk-161、ビッグケミー・ジャパン社製)を6.25質量部投入して、ペイントシェーカーで3時間混合して分散させることにより、緑色顔料分散液を調製した。
表5に示す配合成分及び配合割合に従って、(E)着色剤として、この緑色顔料分散液を用いたカラーフィルター用樹脂組成物(カラーレジスト)を調製した。
なお、表5における(A)共重合体の配合量は、(A)共重合体を合成する際に用いた溶剤を含んでおらず、表5における(B)溶剤の配合量は、(A)共重合体を合成する際に用いた溶剤と追加で配合したプロピレングリコールモノメチルエーテルとを合算したものである。
(1)アルカリ現像性
調製されたカラーフィルター用樹脂組成物を、5cm角のガラス基板(無アルカリガラス基板)上に、露光後の厚さが2.5μmとなるようにスピンコートした後、90℃にて3分間加熱することで溶剤を揮発させ、ガラス基板上に塗布膜を形成した。
次に、塗布膜から100μmの距離に所定のパターンのフォトマスクを配置し、このフォトマスクを介して、塗布膜を露光(露光量150mJ/cm2)し、露光部分を光硬化させた。
次に、0.1質量%の炭酸ナトリウムを含む水溶液を、温度23℃及び圧力0.3MPaでスプレーすることにより、未露光部分を溶解して現像した後、残渣及び現像形態により確認した。
アルカリ現像後の残渣は、アルカリ現像後のパターンを、日立ハイテクノロジーズ社製の電子顕微鏡S-3400を用いて観察することにより確認した。この評価の基準は以下の通りである。
○:残渣なし
×:残渣あり
上記のアルカリ現像性の評価結果を表6に示す。
調製されたカラーフィルター用樹脂組成物を、5cm角のガラス基板(無アルカリガラス基板)上に、ベーキング後の厚さが2.5μmとなるようにスピンコートした後、90℃にて3分間加熱することで溶剤を揮発させ、ガラス基板上に塗布膜を形成した。
次に、塗布膜に波長365nmの光を露光し、露光部分を光硬化させた後、ベーキング温度230℃の乾燥器中に30分間放置して、硬化塗膜を作製した。
容量500mLの蓋付きガラス瓶に、200mLのN-メチル-2-ピロリドンを入れ、60℃の条件下に静置した。その中に上記の硬化塗膜付き試験片を浸漬した後、所定の温度に維持した状態で、30分静置した。
試験片のN-メチル-2-ピロリドンへの浸漬前後の色変化(ΔE*ab)を分光光度計UV-1650PC(島津製作所製)にて測定した。浸漬前後のΔE*abの値が4.5以下のとき、硬化膜の耐溶剤性は良好であるといえる。
上記の耐溶剤性の評価結果を表6に示す。
これに対して、炭素原子数3~10のヒドロキシ基含有溶剤を用いない比較合成例1及び2の(A)共重合体を用いたカラーレジスト(比較例1及び2)は、耐溶剤性が十分ではなく、比較合成例1の(A)共重合体を用いたカラーレジスト(比較例1)は、アルカリ現像性も十分ではなかった。また、(A-1)化合物~(A-3)化合物のうち、(A-2)化合物の含有比率が55モル%である比較合成例3の(A)共重合体を用いたカラーレジスト(比較例3)は、アルカリ現像性は良好であったが、耐溶剤性が十分ではなかった。(A-1)化合物を含まない比較合成例4の(A)共重合体を用いたカラーレジスト(比較例4)は、耐溶剤性は良好であったが、アルカリ現像性が十分ではなかった。(A-2)化合物を含まない比較合成例5の(A)共重合体を用いたカラーレジスト(比較例5)は、アルカリ現像性は良好であったが、耐溶剤性が十分ではなかった。
これに対して、炭素原子数3~10のヒドロキシ基含有溶剤を用いない比較合成例1及び2の(A)共重合体を用いたカラーレジスト(比較例6及び7)は、耐溶剤性が十分ではなく、比較合成例1の(A)共重合体を用いたカラーレジスト(比較例6)は、アルカリ現像性も十分ではなかった。また、(A-1)化合物~(A-3)化合物のうち、(A-2)化合物の含有比率が55モル%である比較合成例3の(A)共重合体を用いたカラーレジスト(比較例8)は、アルカリ現像性は良好であったが、耐溶剤性が十分ではなかった。(A-1)化合物を含まない比較合成例4の(A)共重合体を用いたカラーレジスト(比較例9)は、耐溶剤性は良好であったが、アルカリ現像性が十分ではなかった。(A-2)化合物を含まない比較合成例5の(A)共重合体を用いたカラーレジスト(比較例10)は、アルカリ現像性は良好であったが、耐溶剤性が十分ではなかった。
Claims (5)
- (A)酸基を有する重合性不飽和化合物由来の構成単位(a-1)、下記式(1)で表される構成単位(a-2)並びに他の重合性不飽和化合物由来の構成単位(a-3)を含む共重合体であって、全構成単位の合計を100モル%としたときに構成単位(a-2)を1モル%~50モル%含み、重量平均分子量が1000~50000であり且つ分子量分布(Mw/Mn)が1.5~3.0である共重合体と、
(B)炭素原子数3~10のヒドロキシ基含有溶剤を含む溶剤と、
(C)反応性希釈剤と、
(D)光重合開始剤と、
(E)着色剤と
を含むことを特徴とするカラーフィルター用樹脂組成物。
- 前記構成単位(a-1)の酸基がカルボキシル基であり、前記(A)共重合体が前記構成単位(a-1)を10モル%~50モル%含み、且つ前記(A)共重合体の酸価が20KOHmg/g~300KOHmg/gである請求項1に記載のカラーフィルター用樹脂組成物。
- 前記(B)溶剤を除く成分の総和を100質量部としたときに、前記(A)共重合体の含有量が5質量部~85質量部、前記(C)反応性希釈剤の含有量が5質量部~85質量部、前記(D)光重合開始剤の含有量が0.1質量部~30質量部、前記(E)着色剤の含有量が5質量部~75質量部である請求項1又は2に記載のカラーフィルター用樹脂組成物。
- 前記1~3の何れか一項に記載のカラーフィルター用樹脂組成物から形成された着色パターンを有することを特徴とするカラーフィルター。
- (A-1)酸基を有する重合性不飽和化合物、(A-2)下記式(2)で表される化合物並びに(A-3)他の重合性不飽和化合物からなるモノマー混合物を、(B)溶剤の存在下で共重合させた後、(C)反応性希釈剤、(D)光重合開始剤及び(E)着色剤を添加して混合する工程を含むカラーフィルター用樹脂組成物の製造方法であって、
(A-1)化合物、(A-2)化合物及び(A-3)化合物の合計を100モル%としたときにモノマー混合物が1モル%~50モル%の(A-2)化合物を含み、且つ(B)溶剤が炭素原子数3~10のヒドロキシ基含有溶剤を含むことを特徴とするカラーフィルター用樹脂組成物の製造方法。
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KR20220007628A (ko) | 2019-05-08 | 2022-01-18 | 스미또모 가가꾸 가부시키가이샤 | 착색 경화성 수지 조성물 |
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KR102270594B1 (ko) | 2021-06-28 |
JPWO2018110097A1 (ja) | 2019-10-24 |
TW201829489A (zh) | 2018-08-16 |
JP6890613B2 (ja) | 2021-06-18 |
TWI653248B (zh) | 2019-03-11 |
KR20190086753A (ko) | 2019-07-23 |
CN110073253B (zh) | 2021-10-29 |
CN110073253A (zh) | 2019-07-30 |
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