CN116263562A - Coloring composition, method for producing same, photosensitive coloring composition, color filter, solid-state imaging element, and image display device - Google Patents

Coloring composition, method for producing same, photosensitive coloring composition, color filter, solid-state imaging element, and image display device Download PDF

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Publication number
CN116263562A
CN116263562A CN202211490354.XA CN202211490354A CN116263562A CN 116263562 A CN116263562 A CN 116263562A CN 202211490354 A CN202211490354 A CN 202211490354A CN 116263562 A CN116263562 A CN 116263562A
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meth
acrylate
coloring composition
pigment
compound
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坂口雄哉
髙木悠大
唐木田直人
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Dongyang Yihuan Co ltd
Artience Co Ltd
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Dongyang Yihuan Co ltd
Toyo Ink SC Holdings Co Ltd
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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour filters
    • 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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
    • H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
    • H01L27/144—Devices controlled by radiation
    • H01L27/146—Imager structures
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices

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  • Nonlinear Science (AREA)
  • Power Engineering (AREA)
  • Architecture (AREA)
  • Microelectronics & Electronic Packaging (AREA)
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  • Condensed Matter Physics & Semiconductors (AREA)
  • Mathematical Physics (AREA)
  • Computer Hardware Design (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optical Filters (AREA)
  • Liquid Crystal (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polymerisation Methods In General (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Solid State Image Pick-Up Elements (AREA)

Abstract

The invention relates to a coloring composition, a method for producing the same, a photosensitive coloring composition, a color filter, a solid-state imaging element and an image display device. A coloring composition comprising: the coloring composition comprises a colorant comprising a pigment, a polyester dispersant and a solvent, wherein the polyester dispersant has a main chain based on an aromatic carboxylic acid ester moiety having an ester bond, and a side chain based on a vinyl polymer moiety, the aromatic carboxylic acid ester moiety having an ester bond is a reaction-forming moiety of an aromatic compound having two or more acid anhydride groups and a compound having two or more hydroxyl groups, and the acid anhydride group is 0.9 to 1.5 mol relative to 1 mol of the hydroxyl groups, and the main chain based on the aromatic carboxylic acid ester moiety has a sealing moiety derived from a single alcohol.

Description

Coloring composition, method for producing same, photosensitive coloring composition, color filter, solid-state imaging element, and image display device
Technical Field
The present invention relates to a coloring composition used for forming color filters of liquid crystal display devices, organic Electroluminescence (EL) display devices and other image display devices, and solid-state imaging devices.
Background
In recent years, development of color filters for high color reproduction applications has been advanced in image display devices, and along with this, the required performance of color filter coloring compositions has become strict. Not only the quality of the color filter as a final product becomes difficult, but also the pigment dispersion composition containing a large amount of the coloring composition becomes difficult, and thus the process becomes difficult. In particular, enhancement of resolubility in propylene glycol monomethyl ether acetate (propylene glycol monomethyl ether acetate, PGMAc) is important. When PGMAc is not excellent in resolubility, there is a possibility that a dry film may be generated after a resist solution is coated with a coater, and when PGMAc is not easily resolubilized, the dry film may become a foreign substance at the time of subsequent treatment.
As a method for improving the resolubility of PGMAc, there are: a method using a graft type dispersant (patent document 1) or a method using an acrylic block polymer (patent document 2).
However, these methods have difficulty in achieving both dispersion stability of the coloring composition and PGMAc resolubility.
[ Prior Art literature ]
[ patent literature ]
Patent document 1 japanese patent laid-open publication No. 2009-227839
[ patent document 2] Japanese patent laid-open No. 2020-194131
Disclosure of Invention
[ problem to be solved by the invention ]
The purpose of the present invention is to provide a coloring composition which has excellent storage stability, foreign matter inhibition on a coating film, excellent filterability, and excellent resolubility to PGMAc.
[ means of solving the problems ]
The coloring composition of the present invention is a coloring composition comprising: a colorant comprising a pigment, a polyester dispersant and a solvent,
the polyester dispersant has a main chain based on an aromatic carboxylic acid ester site having an ester bond, which is a reaction formation site of an aromatic compound having two or more acid anhydride groups and a compound having two or more hydroxyl groups, and a side chain based on a vinyl polymer site, and
the acid anhydride group is 0.9 to 1.5 moles relative to 1 mole of the hydroxyl group,
the aromatic carboxylate moiety-based backbone has a seal moiety derived from a monol.
The present invention also relates to the coloring composition, wherein the monoalcohol is a compound having an ether group or a carbonyl group.
The present invention also relates to the coloring composition, wherein the polyester dispersant has a weight average molecular weight of 7000 to 25000.
The present invention also relates to a photosensitive coloring composition comprising: the coloring composition, a photopolymerizable compound, and a photopolymerization initiator.
In addition, the present invention relates to a color filter comprising: a substrate, and a filter segment formed from the photosensitive coloring composition.
In addition, the present invention relates to a solid-state imaging element including the color filter.
In addition, the present invention relates to an image display device including the color filter.
The process for producing a coloring composition of the present invention is a process for producing a coloring composition containing a colorant containing a pigment, a polyester dispersant and a solvent, characterized in that,
the polyester dispersant has a main chain based on an aromatic carboxylic acid ester site having an ester bond, which is a reaction formation site of an aromatic compound having two or more acid anhydride groups and a compound having two or more hydroxyl groups, and a side chain based on a vinyl polymer site, and
the acid anhydride group is 0.9 to 1.5 moles relative to 1 mole of the hydroxyl group,
the aromatic carboxylate moiety-based backbone has a seal moiety derived from a monol.
[ Effect of the invention ]
According to the present invention, a coloring composition having excellent storage stability, foreign matter inhibition on a coating film, excellent filterability, and excellent resolubility with respect to PGMAc can be provided. The present invention also provides a photosensitive coloring composition, a solid-state imaging device, an image display device, and a method for producing the coloring composition.
Detailed Description
Terms of the present specification are defined. In the case of the expression "(meth) acryl", "(meth) acrylic", "(meth) acrylate", or "(meth) acrylamide", the expression "acryl and/or methacryl", "acrylic and/or methacrylic", "acrylate and/or methacrylate", or "acrylamide and/or methacrylamide", respectively, is represented unless otherwise specified. In addition, in the present specification, "c.i." means dye Index (c.i.).
The coloring composition of the present invention contains: a colorant comprising a pigment, a polyester dispersant, and a solvent, wherein in the coloring composition,
the polyester dispersant has a main chain based on an aromatic carboxylic acid ester site having an ester bond, which is a reaction site of 1 mol of a compound having two or more hydroxyl groups and 0.9 to 1.5 mol of an aromatic compound having two or more acid anhydride groups, and a side chain based on a vinyl polymer site,
The aromatic carboxylate moiety-based backbone has a seal moiety derived from a monol.
The polyester dispersant has improved dispersibility by increasing the proportion of the pigment-adsorbed sites in one molecule by forming a main chain based on an aromatic carboxylic acid ester site having an ester bond, which is a reaction-formed site of 1 mol of a compound having two or more hydroxyl groups and 0.9 to 1.5 mol of an aromatic compound having two or more acid anhydride groups. Further, by sealing the acid anhydride group that does not contribute to the reaction site with a monoalcohol, the stability with time and the resolubility with respect to PGMAc are improved.
In general, a dispersant has a site to be adsorbed to a pigment and a site having high affinity to a photopolymerizable compound as a pigment carrier, a binder resin and a solvent as a dispersion medium, and the performance of the dispersant is determined by the balance of these two sites.
That is, in order to exhibit dispersibility, the property of the dispersant to adsorb to the pigment and the affinity to the pigment carrier and the solvent as a dispersion medium are all very important. The pigment carrier as referred to herein comprises a resin from which the pigment component and the dispersant have been removed from the nonvolatile component, and a precursor thereof or a mixture thereof.
< polyester dispersant >)
The polyester dispersant used in the present invention has a main chain based on an aromatic carboxylic acid ester moiety having an ester bond, which is a reaction site of 1 mol of a compound having two or more hydroxyl groups and 0.9 mol to 1.5 mol of an aromatic compound having two or more acid anhydride groups, and a side chain based on a vinyl polymer moiety,
the aromatic carboxylate moiety-based backbone has a seal moiety derived from a monol.
In the polyester dispersant, an ester bond is formed by a ring-opening reaction between an aromatic compound having two or more acid anhydride groups as a precursor and a compound having two or more hydroxyl groups as a precursor, and an aromatic carboxylic acid is formed at the same time.
The vinyl polymer sites of the polyester dispersant used in the present invention can be polymerized by, for example, the following two methods. The first method is a method of polymerizing an ethylenically unsaturated monomer in the presence of a compound having two or more hydroxyl groups. The compound having a hydroxyl group is preferably a compound having a hydroxyl group and a thiol group in the molecule, more preferably a compound having two hydroxyl groups and one thiol group in the molecule.
The second method is a method of polymerizing an ethylenically unsaturated monomer in the presence of a reaction product of an aromatic compound having two or more acid anhydride groups and a hydroxyl group of a compound having two or more hydroxyl groups. Among them, a polymer obtained by polymerizing an ethylenically unsaturated monomer in the presence of a reaction product of a hydroxyl group of a compound having two hydroxyl groups and one thiol group in the molecule and an acid anhydride group of an aromatic tetracarboxylic dianhydride is preferable.
The two methods differ in whether the polymer site obtained by polymerizing the ethylenically unsaturated monomer is introduced first or after the introduction. The molecular weight and the like may be slightly different depending on various conditions, but may be theoretically the same as long as the starting materials are the same as the reaction conditions.
In the main chain based on the aromatic carboxylic acid ester moiety, the aromatic carboxylic acid functions as a pigment adsorbing group. In addition, the aromatic carboxylic acid has a structure in which a carboxyl group is directly bonded to an aromatic ring. In addition, the side chains based on the vinyl polymer sites act as pigment carrier affinity sites. Thus, aggregation of the pigment is suppressed, and the dispersion stability is excellent.
The main chain based on the aromatic carboxylic acid ester moiety is produced by an esterification reaction of 1 mol of a compound having two or more hydroxyl groups with 0.9 mol to 1.5 mol of an aromatic compound having two or more acid anhydride groups. Further, at least one of the acid anhydride groups based on the terminal of the main chain of the aromatic carboxylic acid ester moiety has a sealing moiety derived from a monoalcohol. That is, the acid anhydride group is ring-opened by a monoalcohol to form an alcohol ester and a carboxyl group. This improves the filterability of the coloring composition, suppresses foreign matter on a coating film formed by applying the coloring composition, and improves the resolubility of a cured product derived from the coloring composition formed in the application device with respect to PGMAc when the coloring composition is applied. In the esterification reaction, the amount of the aromatic compound having two or more acid anhydride groups to be used is preferably 1.0 to 1.3 mol.
The side chain based on the vinyl polymer site in the present invention is formed by polymerization of an ethylenically unsaturated monomer. The whole monomer units constituting the vinyl polymer site are partial structures derived from each ethylenically unsaturated monomer after vinyl polymerization.
First, each constituent element of the polyester dispersant of the present invention will be described.
[ aromatic Compound having two or more acid anhydride groups ]
The anhydride group of the aromatic compound having two or more anhydride groups used in the present invention can cause carboxyl groups serving as pigment adsorption groups to be regularly arranged on the main chain of the polyester dispersant by ring-opening reaction with the compound having two or more hydroxyl groups as a precursor, contributing to pigment dispersibility.
Examples of the aromatic compound having two or more acid anhydride groups include: 4,4 '-Dimethyldiphenylsilane tetracarboxylic dianhydride 3,3',4,4 '-Dimethyldiphenylsilane tetracarboxylic dianhydride, 3',4,4 '-tetraphenylsilane tetracarboxylic dianhydride, 1,2,3, 4-furantetracarboxylic dianhydride, 4' -bis (3, 4-dicarboxyphenoxy) diphenyl sulfide dianhydride, 4 '-bis (3, 4-dicarboxyphenoxy) diphenyl sulfone dianhydride, 4' -bis (3, 4-dicarboxyphenoxy) diphenyl propane dianhydride, 3',4,4' -perfluoroisopropylidene diphthalic dianhydride, 3', 4' -biphenyltetracarboxylic dianhydride, bis (phthalic) phenylphosphine oxide dianhydride, p-phenylene-bis (triphenylphthalic) dianhydride, m-phenylene-bis (triphenylphthalic) dianhydride, bis (triphenylphthalic) -4,4 '-diphenyl ether dianhydride, bis (triphenylphthalic) -4,4' -diphenylmethane dianhydride, 9-bis (3, 4-dicarboxyphenyl) fluorene dianhydride, 9-bis [4- (3, 4-dicarboxyphenoxy) phenyl ] fluorene dianhydride, 3, 4-dicarboxy-1, 2,3, 4-tetrahydro-1-naphthalene succinic dianhydride, or 3, 4-dicarboxy-1, 2,3, 4-tetrahydro-6-methyl-1-naphthalene succinic dianhydride, etc.
The aromatic compound having two or more acid anhydride groups represented by the general formula (2) or (3) below may be exemplified as the aromatic tetracarboxylic dianhydride.
General formula (2):
[ chemical 1]
Figure BDA0003964659340000041
[ in the general formula (2), k is 1 or 2]
General formula (3):
[ chemical 2]
Figure BDA0003964659340000042
[ in the general formula (3), Q 1 Is a direct bond, -O-, -CO-, -COOCH 2 CH 2 OCO-、-SO 2 -、-C(CF 3 ) 2 -, a group represented by the following general formula (4), or a group represented by the following general formula (5)]
General formula (4):
[ chemical 3]
Figure BDA0003964659340000051
General formula (5):
[ chemical 4]
Figure BDA0003964659340000052
From the viewpoint of the adsorptivity to pigments, the aromatic compound having two or more acid anhydride groups is preferably aromatic tetracarboxylic dianhydride, more preferably pyromellitic dianhydride.
An aromatic compound having two or more acid anhydride groups may be used in combination with an aliphatic compound having two or more acid anhydride groups.
[ Compound having two or more hydroxyl groups ]
The compound having two or more hydroxyl groups is preferably a compound having a hydroxyl group and a thiol group in the molecule as described above, and more preferably a compound having two hydroxyl groups and one thiol group in the molecule.
Examples of the compound having two hydroxyl groups and one thiol group in the molecule include: 1-mercapto-1, 1-methane diol, 1-mercapto-1, 1-ethane diol, 3-mercapto-1, 2-propane diol (thioglycerol), 2-mercapto-1, 2-propane diol, 2-mercapto-2-methyl-1, 3-propane diol, 2-mercapto-2-ethyl-1, 3-propane diol, 1-mercapto-2, 2-propane diol, 2-mercaptoethyl-2-methyl-1, 3-propane diol, or 2-mercaptoethyl-2-ethyl-1, 3-propane diol, and the like.
Examples of the ethylenically unsaturated monomer include: straight-chain or branched alkyl (meth) acrylates such as methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, isoamyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, cetyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate, isomyristyl (meth) acrylate, stearyl (meth) acrylate, or isostearyl (meth) acrylate, methoxyethyl (meth) acrylate, methoxypolyethylene glycol (meth) acrylate, methoxypolypropylene glycol (meth) acrylate, methoxypolytetramethylene glycol (meth) acrylate, or methoxypolyethylene glycol (meth) acrylate;
cyclic alkyl (meth) acrylates such as cyclohexyl (meth) acrylate, t-butylcyclohexyl (meth) acrylate, dicyclopentanyl alkyl (meth) acrylate, dicyclopentanyloxyethyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, or isobornyl (meth) acrylate;
Fluoroalkyl (meth) acrylates such as trifluoroethyl (meth) acrylate, octafluoropentyl (meth) acrylate, perfluorooctyl ethyl (meth) acrylate, and tetrafluoropropyl (meth) acrylate;
(meth) acryloyloxy-modified polydimethylsiloxanes (silicone macromers);
(meth) acrylic esters having a heterocycle such as tetrahydrofurfuryl (meth) acrylate and 3-methyl-3-oxetanyl (meth) acrylate;
(meth) acrylates having an aromatic ring such as benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, p-cumylphenoxyethyl (meth) acrylate, p-cumylphenoxypolyethylene glycol (meth) acrylate, or nonylphenoxypolyethylene glycol (meth) acrylate;
(meth) acrylates having a carboxyl group such as (meth) acrylic acid, acrylic acid dimer, 2- (meth) acryloyloxyethyl phthalate, 2- (meth) acryloyloxypropyl phthalate, 2- (meth) acryloyloxyethyl hexahydrophthalate, 2- (meth) acryloyloxypropyl hexahydrophthalate, ethylene oxide-modified succinic acid (meth) acrylate, β -carboxyethyl (meth) acrylate, or ω -carboxypolycaprolactone (meth) acrylate;
Vinyl groups such as styrene, α -methylstyrene, vinyl acetate, vinyl (meth) acrylate, or allyl (meth) acrylate;
n-substituted (meth) acrylamides such as (meth) acrylamide, N-dimethyl (meth) acrylamide, N-diethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, diacetone (meth) acrylamide, or acryloylmorpholine;
amino group-containing (meth) acrylates such as N, N-dimethylaminoethyl (meth) acrylate and N, N-diethylaminoethyl (meth) acrylate;
nitriles such as (meth) acrylonitrile; or mixtures thereof.
Examples of the monomer that can be used in combination with the (meth) acrylic monomer include: styrenes such as styrene and α -methylstyrene, vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether and isobutyl vinyl ether, and fatty acid vinyl esters such as vinyl acetate and vinyl propionate.
In addition, a carboxyl group-containing ethylenically unsaturated monomer may be used in combination. The carboxyl group-containing ethylenically unsaturated monomer may be one or more selected from acrylic acid, methacrylic acid, itaconic acid, maleic acid, fumaric acid, crotonic acid, and the like.
The vinyl polymer site may be formed of a vinyl polymer having two hydroxyl groups in a single terminal region. The synthesis thereof includes the following methods in addition to the method of radical polymerization of an ethylenically unsaturated monomer in the presence of a compound having two hydroxyl groups and one thiol group in the molecule.
The method comprises the following steps:
method of Michael addition of a resin having one (meth) acrylic group in one terminal region with a compound having one amino group and two hydroxyl groups
[ 2 ] method for subjecting a resin having a carboxylic acid group in a single terminal region to epoxy addition with a compound having an epoxy group and a hydroxyl group
[ 3 ] method for adding a resin having a vinyl ether group in a single terminal region to a compound having a carboxylic acid group and two hydroxyl groups
[ 4 ] A method of performing radical polymerization or atom transfer radical polymerization (living radical polymerization) using a polymerization initiator having two hydroxyl groups as a polymerization initiator.
By using these methods, a resin having two hydroxyl groups in one terminal region can be synthesized, but in many cases, a multistage reaction is performed or control of molecular weight is difficult, and in terms of productivity, a method of radical polymerizing an ethylenically unsaturated monomer in the presence of a compound having two hydroxyl groups and one thiol group is most preferable.
The vinyl polymer site can be synthesized by polymerizing a compound having two hydroxyl groups and one thiol group in the molecule together with an ethylenically unsaturated monomer. The compound having two hydroxyl groups and one thiol group is used in an amount of 1 to 10% by mass, more preferably 2 to 9% by mass, still more preferably 3 to 8% by mass, based on the total monomer mass of the ethylenically unsaturated monomer. When the content is 1% by mass or more, the molecular weight of the vinyl polymer site does not become excessively high, and the absolute amount thereof can be suppressed as an affinity site for the pigment carrier and the solvent, thereby further improving pigment dispersibility. When the content is 10 mass% or less, the molecular weight of the vinyl polymer site does not become too low, and the effect of steric repulsion can be sufficiently obtained as an affinity site for the pigment carrier and the solvent, and the pigment dispersibility is further improved.
The polymerization temperature is 40℃to 150℃and preferably 50℃to 110 ℃. If the temperature is 40 ℃ or higher, the polymerization is easy to proceed, and if the temperature is 150 ℃ or lower, the control of the molecular weight is easy.
In the polymerization, a polymerization initiator may be used in an amount of 0.001 to 5 mass% based on the total monomer mass of the ethylenically unsaturated monomer. The polymerization initiator may be an azo compound or an organic peroxide.
Examples of the azo compound include: 2,2' -azobisisobutyronitrile, 2' -azobis (2-methylbutyronitrile), 1' -azobis (cyclohexane 1-carbonitrile), 2' -azobis (2, 4-dimethylvaleronitrile), 2' -azobis (2, 4-dimethyl-4-methoxypentanenitrile), dimethyl 2,2' -azobis (2-methylpropionate), 4' -azobis (4-cyanovaleric acid), 2' -azobis (2-hydroxymethylpropionitrile), or 2,2' -azobis [2- (2-imidazolin-2-yl) propane ].
Examples of the organic peroxide include: benzoyl peroxide, t-butyl peroxybenzoate, cumene hydroperoxide, diisopropyl peroxydicarbonate, di-n-propyl peroxydicarbonate, di (2-ethoxyethyl) peroxydicarbonate, t-butyl peroxyneodecanoate, t-butyl peroxytrimethylacetate, peroxy (3, 5-trimethylhexanoyl), dipropyl peroxide, or diacetyl peroxide, and the like.
The polymerization initiator may be used singly or in combination of two or more.
The synthesis of the vinyl polymer is preferably performed by bulk polymerization or solution polymerization. Examples of the polymerization solvent for solution polymerization include: ethyl acetate, n-butyl acetate, isobutyl acetate, toluene, xylene, acetone, hexane, methyl ethyl ketone, cyclohexanone, propylene glycol monomethyl ether acetate, dipropylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, or the like, but are not particularly limited thereto. These polymerization solvents may be used in combination of two or more.
The side chains of the polyester dispersants may have sites based on other polyols in addition to vinyl polymer sites.
[ other polyols ]
In the polymerization, the density of the carboxylic acid groups and the ratio of the solvent-dissolved portions can be easily adjusted by using other polyols in combination.
Examples of other polyols include: polyhydric alcohols such as ethylene glycol, propylene glycol, 1, 3-propanediol, 1, 4-butanediol, 1, 3-butanediol, 1, 5-pentanediol, neopentyl glycol, 1, 6-hexanediol, 1, 4-bis (hydroxymethyl) cyclohexane, bisphenol a, hydrogenated bisphenol a, hydroxy-trimethylacetyl hydroxy-trimethyl acetate, trimethylolethane, trimethylolpropane, 2, 4-trimethyl-1, 3-pentanediol, glycerol, or hexanetriol;
various polyether glycols such as polyoxyethylene glycol, polyoxypropylene glycol, polyoxyethylene polyoxytetramethylene glycol, polyoxypropylene polyoxytetramethylene glycol, or polyoxyethylene polyoxypropylene polyoxytetramethylene glycol;
modified polyether polyols obtained by ring-opening polymerization of the above-mentioned various polyols with various (cyclic) ether bond-containing compounds such as ethylene oxide, propylene oxide, tetrahydrofuran (tetrahydrofuran), ethyl glycidyl ether, propyl glycidyl ether, butyl glycidyl ether, phenyl glycidyl ether, or allyl glycidyl ether;
As the polyester polyol obtained by co-condensing one or more of the above various polyols with a polycarboxylic acid, and as the polycarboxylic acid, a polyol obtained from a particularly typical polycarboxylic acid such as succinic acid, adipic acid, sebacic acid, azelaic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, maleic acid, fumaric acid, citraconic acid, itaconic acid, glutaconic acid, 1,2, 5-hexanetricarboxylic acid, 1, 4-cyclohexanedicarboxylic acid, 1,2, 4-benzenetricarboxylic acid, 1,2, 5-benzenetricarboxylic acid, 1,2, 4-cyclohexanedicarboxylic acid, or 2,5, 7-naphthalenetricarboxylic acid;
lactone-based polyester polyols obtained by polycondensation of one or more of the above polyols with various lactones such as epsilon-caprolactone, delta-valerolactone or 3-methyl-delta-valerolactone, or lactone-modified polyester polyols obtained by polycondensation of the above polyols with a polycarboxylic acid or various lactones;
in the synthesis of polyester polyols, epoxy-modified polyester polyols obtained by using one or more bisphenol A type epoxy compounds, hydrogenated bisphenol A type epoxy compounds, glycidyl ethers of monohydric and/or polyhydric alcohols, or various epoxy compounds such as glycidyl esters of monobasic and/or polybasic acids; or a polyester polyamide polyol, a polycarbonate polyol, a polybutadiene polyol, a polypentadiene polyol, castor oil, a castor oil derivative, hydrogenated castor oil, a hydrogenated castor oil derivative, a hydroxyl group-containing acrylic copolymer, a hydroxyl group-containing fluorine compound, a hydroxyl group-containing silicone resin, or the like.
The other polyols may be used alone or in combination of two or more, and the weight average molecular weight thereof is preferably 40 to 10,000, more preferably 100 to 2,000, and even more preferably 100 to 1,000 from the viewpoint of compatibility and dispersion stability. When the weight average molecular weight is 40 or more, the density of the carboxylic acid groups can be adjusted. When the weight average molecular weight is 10,000 or less, compatibility with other raw materials becomes good.
As the other polyol, a diol is preferable. In particular, by reacting with an aromatic compound having two or more acid anhydride groups, carboxyl groups serving as pigment adsorption groups can be regularly arranged in the main chain, which is advantageous for pigment dispersion. If a large amount of polyhydric alcohol having more than two hydroxyl groups is used, the main chain of the polyester becomes branched to be complicated and bulky, and it is difficult to obtain a dispersing effect. In order to adjust the molecular weight of the polyester dispersant, adjust the viscosity of the dispersion, etc., it should be limited to a minimum in view of design. The amount of the adjustment will be described later.
[ Synthesis of polyester ]
The process of polyester synthesis of the polyester dispersant used in the present invention will be described by taking as an example the reaction of a compound having two hydroxyl groups and tetracarboxylic dianhydride as each preferable compound of a compound having two or more hydroxyl groups and an aromatic compound having two or more acid anhydride groups.
The tetracarboxylic dianhydride used in the present invention can react with hydroxyl groups to form ester bonds, and a pendant carboxyl group remains on the resulting polyester backbone. The reaction of a tetracarboxylic dianhydride with a compound having two hydroxyl groups when i) a > b, ii) a=b, and iii) a < b, assuming that the molar amount of the compound having two hydroxyl groups is a, and assuming that the molar amount of the tetracarboxylic dianhydride is b, is shown in the following general formulae (6), (7), and (8). If the residual acid anhydride groups in the products of the following general formulae (6) to (8) are hydrolyzed or the ring-opening of the acid anhydride is performed by alcohol, the product obtained by the reaction has two or three carboxyl groups in the X1 portion in the structural formula, and the plurality of carboxyl groups are effective as adsorption sites of the pigment.
i)a＞b
General formula (6):
[ chemical 5]
Figure BDA0003964659340000081
ii)a＝b
General formula (7):
[ chemical 6]
Figure BDA0003964659340000091
iii)a＜b
General formula (8):
[ chemical 7]
Figure BDA0003964659340000092
R represents a hydrogen atom in the case of hydrolyzing an acid anhydride group, and represents a structure of a monoalcohol described later in the case of opening an acid anhydride by using the monoalcohol.
X in the present invention 1 Is a reaction residue after the reaction of the tetracarboxylic dianhydride with the hydroxyl groups, and Y is a reaction residue after the reaction of the compound having two hydroxyl groups with the acid anhydride groups. As X 1 Preferably, the tetracarboxylic dianhydride represented by the general formula (2) or (3) is a reaction residue obtained by reacting a compound having two hydroxyl groups.
[ Synthesis of polyester dispersant ]
In the description of the synthesis of the polyesters represented by the general formulae (6) to (8), the polyester dispersant is preferably a method in which a vinyl polymer is introduced via an S atom into Y in a compound having two hydroxyl groups. Hereinafter, two preferable modes of synthesis are shown.
Synthetic pattern 1)
In the following general formula (9), an ethylenically unsaturated monomer is radically polymerized in the presence of a compound (a 1) having two hydroxyl groups and one thiol group at one end to produce a vinyl polymer (a 2) having two hydroxyl groups at one end, and this is reacted with a tetracarboxylic dianhydride (b 1).
General formula (9):
[ chemical 8]
Figure BDA0003964659340000101
If the molar ratio of (a 1) is a (integer) and the molar ratio of (b) is b (integer), the molar ratio of the present invention is preferably 2 b/2a=b/a=0.9 to 1.5. When the molar ratio is less than 1, unreacted acid anhydride may remain, and the main chain end may be sealed with a monoalcohol. When the molar ratio b/a is 0.9 or more, the proportion of the sites adsorbed to the pigment in one molecule is sufficient, and the generation of foreign matter is suppressed, and when it is 1.5 or less, no acid anhydride group remains, and the storage stability is good, and even if the acid anhydride is ring-opened, the acid group is not excessive, and the compatibility with the pigment carrier or the solvent is good. From the viewpoint of pigment dispersibility and stability, b/a=1.0 to 1.3 is more preferable.
Synthetic pattern 2
In the following general formulae (10) and (11), a compound having two hydroxyl groups and one thiol group at one end is reacted with tetracarboxylic dianhydride to initially produce a compound containing no vinyl polymer site, and then the remaining thiol group is subjected to radical polymerization as a chain transfer agent to introduce the vinyl polymer site.
General formula (10):
[ chemical 9]
Figure BDA0003964659340000111
General formula (11)
[ chemical 10]
Figure BDA0003964659340000112
If the molar ratio of (a 1) is a (integer) and the molar ratio of (b) is b (integer), the molar ratio of the present invention is preferably 2 b/2a=b/a=0.9 to 1.5. When the molar ratio is less than 1, unreacted acid anhydride may remain, and the acid anhydride may be ring-opened by a monoalcohol. The ring-opening reaction of the acid anhydride using the monoalcohol may be carried out before the radical polymerization as in the general formula (10) or after the radical polymerization as in the general formula (11). When the molar ratio b/a is 0.9 or more, the proportion of the sites adsorbed to the pigment in one molecule is sufficient, and the generation of foreign matter is suppressed, and when it is 1.5 or less, no acid anhydride group remains, and the storage stability is good, and even if the acid anhydride is ring-opened, the acid group is not excessive, and the compatibility with the pigment carrier or the solvent is good. From the viewpoint of pigment dispersibility and stability, b/a=1.0 to 1.3 is more preferable.
[ reaction catalyst ]
The catalyst used in the synthesis of the polyester dispersant is preferably a tertiary amine compound. Examples of the tertiary amine compound include: triethylamine, triethylenediamine, N-dimethylbenzylamine, N-methylmorpholine, 1, 8-diazabicyclo- [5.4.0] -7-undecene, or 1, 5-diazabicyclo- [4.3.0] -5-nonene, and the like.
[ reaction solvent ]
Solvents may be used in the synthesis of the polyester dispersants. Examples of the solvent include: acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, cyclopentanone, ethyl acetate, butyl acetate, toluene, xylene, acetonitrile, propylene glycol monomethyl ether acetate, and the like.
The main chain based on the aromatic carboxylic acid ester moiety in the polyester dispersant has a sealing moiety derived from a monoalcohol obtained by reacting a monoalcohol with an acid anhydride group.
Examples of the monoalcohol include: a single alcohol such as methanol, ethanol, 1-butanol, 2-butanol, isobutanol (iso-butanol), t-butanol, 1-pentanol (1-pentanol), isopentyl alcohol, t-amyl alcohol, cyclopentanol, 1-hexanol, cyclohexanol, 1-heptanol, 1-octanol, 2-ethyl-1-hexanol, isononyl alcohol, 1-nonyl alcohol, amyl alcohol (amyl alcohol), lauryl alcohol, n-butyl alcohol, isobutyl alcohol, cyclohexanol, benzyl alcohol, methyl cyclohexanol; 3-methoxy-3-methyl-1-butanol, 3-methoxybutanol, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-tertiary butyl ether, ethylene glycol monobutyl ether, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monobutyl ether, diethylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol monophenyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, and the like; and monoalcohols having a carbonyl group such as methyl lactate, ethyl lactate and diacetone alcohol. These may be used singly or in combination of two or more.
The monoalcohol is preferably a compound having an ether group or a carbonyl group. An ether group or a carbonyl group may be provided at a terminal of the main chain of the dispersant, so that PGMAc resolubility of the dispersant is improved. Among these, 3-methoxybutanol, propylene glycol monomethyl ether, diacetone alcohol are preferable.
The main chain based on the aromatic carboxylate moiety may have a sealing moiety obtained by reacting with water in addition to a sealing moiety derived from a monoalcohol.
The amount of the monoalcohol to be used is preferably 1 to 30 equivalents, more preferably 1.5 to 20 equivalents, relative to 1 equivalent of the acid anhydride group remaining in the main chain, in the synthesis of the sealing site. When the amount is 1 equivalent or more, no acid anhydride group remains, and the storage stability is good, and when the amount is 30 equivalent or less, transesterification reaction by an ester bond between a monoalcohol and a dispersant is less likely to occur, and the reduction in molecular weight is less likely to occur.
[ reaction conditions ]
The ring-opening reaction temperature in the polyester synthesis is in the range of 50℃to 180℃and preferably 80℃to 140 ℃. When the reaction temperature is 50 ℃ or higher, the reaction proceeds, and when the reaction temperature is 180 ℃ or lower, the esterification reaction between the carboxyl group and the hydroxyl group does not occur, and the decrease in acid value and gelation are less likely to occur.
[ molecular weight ]
The weight average molecular weight of the polyester dispersant is preferably 2,000 to 35,000, more preferably 4,000 to 30,000, and still more preferably 4,000 to 25,000. When the molecular weight is 2,000 or more, pigment aggregation can be suppressed and pigment dispersibility can be further improved by the steric repulsion effect by the solvent affinity site. When the molecular weight is 35,000 or less, the solvent solubility is ensured, a sufficient steric repulsion effect can be maintained, and the pigment dispersibility is further improved. When the content falls within the above range, the pigment aggregation inhibition effect by the steric repulsion effect becomes more excellent.
[ acid value ]
The acid value of the polyester dispersant is preferably 5mgKOH/g to 200mgKOH/g, more preferably 20mgKOH/g to 180mgKOH/g, still more preferably 30mgKOH/g to 150mgKOH/g. When the acid value is 5mgKOH/g or more, the pigment adsorption ability is improved and the pigment dispersibility is further improved. On the other hand, when the viscosity is 200mgKOH/g or less, there is no interaction between the resins, and the viscosity of the pigment-dispersion composition can be suppressed to be low.
The content of the polyester dispersant in the coloring composition is preferably 0.01 to 100% by mass, more preferably 0.01 to 60% by mass, and even more preferably 5 to 40% by mass, based on the mass of the pigment. When the content of the polyester dispersant is 0.01 mass% or more, a good dispersing effect can be obtained, and when the content is 100 mass% or less, there is no interaction between resins, and the viscosity of the pigment-dispersed composition can be suppressed to be low.
< colorant >
The colorant comprises a pigment. Examples of the pigment include organic pigments and inorganic pigments. The pigment is preferably a pigment having high color development and high heat resistance, and in particular, an organic pigment is preferable in terms of high thermal decomposition resistance. Specific examples of the organic pigment that can be used in the color composition for color filters are indicated below by the dye index number.
Examples of the red pigment include: c.i. pigment red (1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48: 1. 48: 2. 48: 3. 48: 4. 49, 49: 1. 49: 2. 50: 1. 52: 1. 52: 2. 53, 53: 1. 53: 2. 53: 3. 57, 57: 1. 57: 2. 58: 4. 60, 63: 1. 63: 2. 64, 64: 1. 68, 69, 81: 1. 81: 2. 81: 3. 81: 4. 83, 88, 90: 1. 101, 101: 1. 104, 108: 1. 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 184, 185, 187, 188, 190, 193, 194, 200, 202, 206, 207, 208, 209, 210, 214, 216, 220, 221, 224, 230, 231, 232, 233, 235, 236, 237, 238, 239, 242, 243, 245, 247, 249, 250, 251, 253, 254, 255, 256, 257, 258, 259, 260, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, 277, 279, 280, 281, 282, 283, 284, 285, 286, 287, 291, 295, 296, the pigment described in japanese patent laid-open publication No. 2014-134, the pigment described in japanese patent publication No. 6368844, etc. Among these, c.i. pigment red 48 is preferable from the viewpoints of heat resistance, light resistance, and transmittance of the filter segment: 1. 122, 177, 224, 242, 269, 254, 291, 295, 296, the pigment described in japanese patent application laid-open publication No. 2014-134712, the pigment described in japanese patent application laid-open publication No. 6368844, and more preferably c.i. pigment red 177, 254, 291, 295, 296, the pigment described in japanese patent application laid-open publication No. 2014-134712, and the pigment described in japanese patent application laid-open publication No. 6368844.
Examples of orange pigments include: c.i. pigment orange (pigment orange) 36, 38, 43, 51, 55, 59, 61, 71 or 73, etc.
Examples of blue pigments include: c.i. pigment blue (pigment blue) 1, 1: 2. 9, 14, 15: 1. 15: 2. 15: 3. 15: 4. 15:6. 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56: 1. 60, 61: 1. 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, 79, etc. Among these, c.i. pigment blue 15, 15 are preferable from the viewpoints of heat resistance, light resistance, and transmittance of the filter segment: 1. 15: 2. 15: 3. 15: 4. or 15:6, further preferred is c.i. pigment blue 15:6. the blue coloring composition may contain a violet pigment as described below.
Examples of violet pigments include: c.i. pigment violet (pigment violet) 1, 1: 1. 2, 2: 2. 3, 3: 1. 3: 3. 5, 5: 1. 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, 50, etc. Among these, c.i. pigment violet 19 or 23 is preferable, and c.i. pigment violet 23 is more preferable from the viewpoints of heat resistance, light resistance and transmittance of the filter segment.
Examples of the green pigment include: pigment green (pigment green) 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 37, 45, 48, 50, 51, 54, 55, 58, 59, 62, 63, pigment described in japanese patent application laid-open No. 2017-111398, and the like. Among these, pigments described in c.i. pigment green 36, 58, 59, 62, 63 and japanese patent laid-open publication No. 2017-111398 are preferable from the viewpoint of transmittance.
Examples of the yellow pigment include: c.i. pigment yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35: 1. 36, 36: 1. 37, 37: 1. 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 192, 193, 194, 196, 198, 199, 213, 214, 231, 233, pigment described in japanese patent laid-open publication No. 2012-226110, and the like. Pigment yellow 138, 139, 150, 185, 231, 233, and pigment described in japanese patent laid-open publication No. 2012-226110 are preferable.
Examples of blue pigments include: c.i. pigment blue 15: 1. 15: 2. 15: 4. 15: 3. 15: 6. 16, 81, etc.
Examples of violet pigments include: c.i. pigment violet 1, 19, c.i. pigment red 144, 146, 177, 169, 81, etc.
Examples of the inorganic pigment include: barium sulfate, zinc white, lead sulfate, chrome yellow, zinc yellow, red iron oxide (red iron (III) oxide), cadmium red, ultramarine, prussian blue, chrome oxide green, cobalt green, umber (umber), titanium black, synthetic iron black, titanium oxide, metal sulfide powder, metal powder, or the like. The inorganic pigment is used in combination with the organic pigment in order to balance the chroma and brightness and ensure good coatability, sensitivity, developability, and the like.
The coloring composition of the present invention may contain a dye within a range that does not lower heat resistance.
< binder resin >
When a film having a thickness of 2 μm is formed, the binder resin preferably has a transmittance of 80% or more, more preferably 95% or more in the entire wavelength region of 400nm to 700nm in the visible light region. Examples of the resin include thermoplastic resins and photosensitive resins.
Examples of the thermoplastic resin include: butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyurethane-based resin, polyester resin, acrylic resin, alkyd (alkyd) resin, polystyrene, polyamide resin, rubber-based resin, cyclized rubber-based resin, cellulose-based, polyethylene, polybutadiene, polyimide resin, or the like.
Examples of the thermosetting resin include: epoxy resin, benzoguanamine resin, rosin-modified maleic acid resin, rosin-modified fumaric acid resin, melamine resin, urea resin, phenol resin, or the like.
The photosensitive resin is preferably, for example: a resin in which a photocrosslinkable group such as a (meth) acryloyl group or a styryl group is introduced into a polymer by reacting a (meth) acrylic compound or cinnamic acid having a reactive substituent such as an isocyanate group, an aldehyde group or an epoxy group with the polymer having a reactive substituent such as a hydroxyl group, a carboxyl group or an amino group. In addition, a resin obtained by half-esterifying a polymer containing an acid anhydride such as a styrene-maleic anhydride copolymer or an α -olefin-maleic anhydride copolymer with a (meth) acrylic acid compound having a hydroxyl group such as a hydroxyalkyl (meth) acrylate is also preferable.
In the case of forming the filter segment by alkali development using the coloring composition of the present invention, it is preferable to contain an alkali-soluble non-photosensitive resin. The alkali-soluble non-photosensitive resin is a resin which is dissolved in an alkali aqueous solution and is not crosslinked by a radical, and examples thereof include a resin having an acidic functional group such as a carboxyl group or a sulfone group and having a weight average molecular weight of 1,000 ～ 500,000, preferably 5,000 ～ 100,000. Specific examples of the alkali-soluble non-photosensitive resin include: acrylic resins having acidic functional groups, alpha-olefin/maleic acid (anhydride) copolymers, styrene/styrene sulfonic acid copolymers, ethylene/(meth) acrylic acid copolymers, or isobutylene/maleic acid (anhydride) copolymers, and the like. Among them, at least one resin selected from the group consisting of an acrylic resin having an acidic functional group, an α -olefin/maleic acid (anhydride) copolymer, a styrene/maleic acid (anhydride) copolymer, and a styrene/styrene sulfonic acid copolymer, particularly an acrylic resin having an acidic functional group is preferably used because of its high heat resistance and transparency.
The photosensitive coloring composition of the present invention preferably contains a coloring composition, a photopolymerizable compound, and a photopolymerization initiator. The coloring composition and the photosensitive coloring composition are preferably used for color filter applications.
< photopolymerizable Compound >)
The photopolymerizable compound is a monomer or oligomer having a polymerizable unsaturated group. Examples of the polymerizable unsaturated group include: vinyl, (meth) acryl, (meth) allyl, and the like.
Examples of the photopolymerizable compound include: straight-chain or branched alkyl (meth) acrylates such as methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, isoamyl (meth) acrylate, octyl (meth) acrylate, isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, cetyl (meth) acrylate, decyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate, isomyristyl (meth) acrylate, stearyl (meth) acrylate, or isostearyl (meth) acrylate;
Cyclic alkyl (meth) acrylates such as cyclohexyl (meth) acrylate, t-butylcyclohexyl (meth) acrylate, dicyclopentanyl alkyl (meth) acrylate, dicyclopentanyloxyethyl (meth) acrylate, dicyclopentenyloxyethyl (meth) acrylate, or isobornyl (meth) acrylate;
fluoroalkyl (meth) acrylates such as trifluoroethyl (meth) acrylate, octafluoropentyl (meth) acrylate, perfluorooctyl ethyl (meth) acrylate, and tetrafluoropropyl (meth) acrylate;
(meth) acryloyloxy-modified polydimethylsiloxanes (silicone macromers);
(meth) acrylic esters having a heterocycle such as tetrahydrofurfuryl (meth) acrylate and 3-methyl-3-oxetanyl (meth) acrylate;
(meth) acrylates having an aromatic ring such as benzyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxypolyethylene glycol (meth) acrylate, p-cumylphenoxyethyl (meth) acrylate, p-cumylphenoxypolyethylene glycol (meth) acrylate, or nonylphenoxypolyethylene glycol (meth) acrylate;
(poly) alkylene glycol monoalkyl ether (meth) acrylates such as 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, 2-methoxypropyl (meth) acrylate, diethylene glycol monomethyl ether (meth) acrylate, diethylene glycol monoethyl ether (meth) acrylate, triethylene glycol monoethyl ether (meth) acrylate, diethylene glycol mono-2-ethylhexyl ether (meth) acrylate, dipropylene glycol monomethyl ether (meth) acrylate, tripropylene glycol mono (meth) acrylate, polyethylene glycol monolauryl ether (meth) acrylate, or polyethylene glycol monolearyl ether (meth) acrylate; (meth) acrylates having a carboxyl group such as (meth) acrylic acid, acrylic acid dimer, 2- (meth) acryloyloxyethyl phthalate, 2- (meth) acryloyloxypropyl phthalate, 2- (meth) acryloyloxyethyl hexahydrophthalate, 2- (meth) acryloyloxypropyl hexahydrophthalate, ethylene oxide-modified succinic acid (meth) acrylate, β -carboxyethyl (meth) acrylate, or ω -carboxypolycaprolactone (meth) acrylate;
Hydroxy group-containing (meth) acrylates such as 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-acryloyloxyethyl-2-hydroxyethyl (meth) acrylate, diethylene glycol mono (meth) acrylate, dipropylene glycol mono (meth) acrylate, polyethylene glycol mono (meth) acrylate, propylene glycol mono (meth) acrylate, polypropylene glycol mono (meth) acrylate, polytetramethylene glycol mono (meth) acrylate, poly (ethylene glycol-propylene glycol) mono (meth) acrylate, poly (ethylene glycol-tetramethylene glycol) mono (meth) acrylate, poly (propylene glycol-tetramethylene glycol) mono (meth) acrylate, or glycerol (meth) acrylate;
(poly) alkylene glycol di (meth) acrylates such as ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, poly (ethylene glycol-propylene glycol) di (meth) acrylate, poly (ethylene glycol-tetramethylene glycol) di (meth) acrylate, poly (propylene glycol-tetramethylene glycol) di (meth) acrylate, polytetramethylene glycol di (meth) acrylate, 1, 3-butanediol di (meth) acrylate, neopentyl glycol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, 1, 9-nonanediol di (meth) acrylate, or 2-butyl-propylene glycol di (meth) acrylate;
Di (meth) acrylates such as dimethylol dicyclopentanedi (meth) acrylate, hydroxy trimethylacetic acid neopentyl glycol di (meth) acrylate, stearic acid modified pentaerythritol di (meth) acrylate, ethylene oxide modified bisphenol a di (meth) acrylate, propylene oxide modified bisphenol a di (meth) acrylate, tetrahydrofuran (tetramethylene oxide) modified bisphenol a di (meth) acrylate, ethylene oxide modified bisphenol F di (meth) acrylate, propylene oxide modified bisphenol F di (meth) acrylate, tetrahydrofuran (tetramethylene oxide) modified bisphenol F di (meth) acrylate, zinc diacrylate, ethylene oxide modified phosphoric acid triacrylate, or glycerol di (meth) acrylate;
(meth) acrylates having a tertiary amino group such as dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, or diethylaminopropyl (meth) acrylate;
multifunctional (meth) acrylates having three or more functions such as glycerol tri (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa (meth) acrylate;
Glycerol triglycidyl ether- (meth) acrylic acid adduct, glycerol diglycidyl ether- (meth) acrylic acid adduct, polyglycerol polyglycidyl ether- (meth) acrylic acid adduct, 1, 6-butanediol diglycidyl ether, alkyl glycidyl ether- (meth) acrylic acid adduct, allyl glycidyl ether- (meth) acrylic acid adduct, phenyl glycidyl ether- (meth) acrylic acid adduct, styrene oxide- (meth) acrylic acid adduct, bisphenol a diglycidyl ether- (meth) acrylic acid adduct, propylene oxide modified bisphenol a diglycidyl ether- (meth) acrylic acid adduct, bisphenol F diglycidyl ether- (meth) acrylic acid adduct, epichlorohydrin modified phthalic acid- (meth) acrylic acid adduct, epichlorohydrin modified hexahydrophthalic acid- (meth) acrylic acid adduct, ethylene glycol diglycidyl ether- (meth) acrylic acid adduct, polyethylene glycol diglycidyl ether- (meth) acrylic acid adduct, polypropylene glycol diglycidyl ether- (meth) acrylic acid adduct, phenol epoxy resin- (meth) acrylic acid adduct, novolac type epoxy resin, and epoxy resin, or epoxy (meth) acrylates such as other epoxy resin- (meth) acrylic acid adducts;
(meth) acryl-modified resin oligomers such as (meth) acryl-modified isocyanurate, (meth) acryl-modified polyurethane, (meth) acryl-modified polyester, (meth) acryl-modified melamine, (meth) acryl-modified silicone, (meth) acryl-modified polybutadiene, or (meth) acryl-modified rosin;
vinyl groups such as styrene, α -methylstyrene, vinyl acetate, vinyl (meth) acrylate, or allyl (meth) acrylate;
vinyl ethers such as hydroxyethyl vinyl ether, ethylene glycol divinyl ether, and pentaerythritol trivinyl ether;
amides such as (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, and N-vinylformamide; or acrylonitrile, etc.
The photopolymerizable compound may be used alone or in combination of two or more.
< photopolymerization initiator >)
Examples of the photopolymerization initiator include: acetophenone photopolymerization initiators such as 4-phenoxydichloroacetophenone, 4-tert-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1-hydroxycyclohexylphenyl ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinylphenyl) -butan-1-one, or 2-methyl-1- [4- (methylthio) phenyl ] -2-morpholinopropane-1-one;
Benzoin photopolymerization initiators such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzil dimethyl ketal;
benzophenone-based photopolymerization initiators such as benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, and 4-benzoyl-4' -methyldiphenyl sulfide;
thioxanthone photopolymerization initiators such as thioxanthone (thioxanthone), 2-chlorothioxanthone, 2-methyl thioxanthone, isopropyl thioxanthone, and 2, 4-diisopropyl thioxanthone;
triazine-based photopolymerization initiators such as 2,4, 6-trichloro-s-triazine, 2-phenyl-4, 6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4, 6-bis (trichloromethyl) -s-triazine, 2-piperonyl-4, 6-bis (trichloromethyl) -s-triazine, 2, 4-bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphtho-1-yl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (4-methoxy-naphtho-1-yl) -4, 6-bis (trichloromethyl) -s-triazine, 2, 4-trichloromethyl- (piperonyl) -6-triazine, or 2, 4-trichloromethyl (4' -methoxystyryl) -6-triazine;
a borate-based photopolymerization initiator;
Carbazole-based photopolymerization initiator;
imidazole-based photopolymerization initiators, and the like.
The photopolymerization initiator may be used alone or in combination of two or more.
The content of the photopolymerization initiator is preferably 5 to 200 parts by mass, more preferably 10 to 150 parts by mass, relative to 100 parts by mass of the pigment.
The photosensitive coloring composition may be used in combination of a photopolymerization initiator and a sensitizer. Thus, photoreactivity is improved. Examples of the sensitizer include: alpha-acyloxy esters, acylphosphine oxides, methyl benzoylformate (methyl phenyl glyoxylate), benzil, 9, 10-phenanthrenequinone, camphorquinone, ethylanthraquinone, 4' -diethylisophthalophenone (4, 4' -diethyl isophthalophenone), 3', 4' -tetrakis (t-butylperoxycarbonyl) benzophenone, or 4,4' -diethylaminobenzophenone, and the like.
The content of the sensitizer is preferably 0.1 to 60 parts by mass relative to 100 parts by mass of the photopolymerization initiator.
< solvent >
The coloring composition or photosensitive coloring composition of the present invention may contain a solvent for the purpose of adjusting viscosity or the like.
Examples of the solvent include: 1,2, 3-trichloropropane, 1,3-butanediol (1, 3-butylodiol), 1,3-butanediol (1, 3-butyl glycol), 1,3-butanediol diacetate, 1, 4-dioxane, 2-heptanone, 2-methyl-1, 3-propanediol, 3, 5-trimethyl-2-cyclohexen-1-one, 3, 5-trimethylcyclohexanone, ethyl 3-ethoxypropionate, 3-methyl-1, 3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene, N-dimethylacetamide, N, N-dimethylformamide, N-butyl alcohol, N-butylbenzene, N-propyl acetate, N-methylpyrrolidone, o-xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, t-butylbenzene, gamma-butyrolactone, isobutyl alcohol, isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol mono-tert-butyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, diacetone alcohol, glyceryl triacetate (triacetin), tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol, methyl isobutyl ketone, methylcyclohexanol, n-pentyl acetate, n-butyl acetate, isopentyl acetate, isobutyl acetate, propyl acetate, or dibasic acid esters, and the like. The solvent may be used alone or in combination of two or more.
The coloring composition of the present invention is prepared by, for example, performing a dispersion treatment using a pigment, a polyester dispersant, a solvent, or the like. When the pigment is an organic pigment, the organic pigment can be dispersed more finely by using a dispersing aid such as a pigment derivative in combination during the dispersion treatment, and when the solubility of the pigment in a solvent is high, the dispersion treatment may not be necessary. In the case where two or more pigments are used in combination, the coloring composition may be prepared separately for each pigment, and then mixed. In addition, the coloring composition can be prepared by using a plurality of pigments.
Next, a photopolymerizable compound, a photopolymerization initiator, and the like are blended and mixed in the colored composition, thereby obtaining a photosensitive colored composition. The timing of blending the respective materials is, of course, arbitrary.
For example, a dispersing device such as a kneader (kneader), a twin roll mill (two-roll mill), a three roll mill (three-roll mill), a ball mill (ball mill), a horizontal sand mill, a vertical sand mill, an annular type bead mill, or an attritor (attritor) can be used for the dispersing treatment.
After the production of the coloring composition and the photosensitive coloring composition, coarse particles of 5 μm or more, preferably 1 μm or more, more preferably 0.5 μm or more, and dust mixed therein are removed by centrifugal separation, a sintered filter, a membrane filter, or the like.
< other dispersants >
In this specification, other dispersants may be used in combination in addition to the polyester dispersant. Examples of the other dispersant include resin dispersants other than polyester dispersants, surfactants, and the like.
Examples of the resin-type dispersing agent other than the polyester dispersing agent include: anionic resin type pigment dispersants such as styrene-maleic anhydride copolymer, olefin-maleic anhydride copolymer, poly (meth) acrylate, styrene- (meth) acrylic acid copolymer, (meth) acrylic acid- (meth) acrylic acid alkyl ester copolymer, (meth) acrylic acid-polyvinyl type macromonomer copolymer, phosphate group-containing acrylic resin, aromatic carboxyl group-containing acrylic resin, polystyrene sulfonate, acrylamide- (meth) acrylic acid copolymer, carboxymethyl cellulose, polyurethane having carboxyl group, formalin condensate of naphthalene sulfonate, or sodium alginate;
nonionic resin-based pigment dispersants such as polyvinyl alcohol, polyalkylene polyamine, polyacrylamide, and polymer starch; or alternatively
Polyethyleneimine, aminoalkyl (meth) acrylate copolymer, polyvinylimidazoline, polyurethane having an amino group, a reaction product of poly (lower alkylene imine) and polyester having a free carboxyl group, or a cationic resin-based pigment dispersant such as chitosan (satkinsan).
Commercially available resin dispersants include: disppapik (Dispersbyk) -101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, 170, 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, 2020, 2025, 2050, 2070, 2095, 2150, 2155, or Antetiara (Anti-Terra) -U, 203, 204, or BYK-P104, P104S, 220S, 6919, or Lactimon (Lactimon), lactimon) -WS, or Bi Kemen (Bykume) manufactured by BYK Chemie Japan (BYK Chemie Japan) company, SOLSPERSE) -3000, 9000, 13000, 13240, 13650, 13940, 16000, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 76500 and the like manufactured by Lubrizol (Lubrizol) corporation, an alvuka (EFKA) -46, 47, 48, 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050, 4055, 4060, 4080, 4400, 4401, 4402, 4403, 4406, 4408, 4300, 4310, 4320, 4330, 4340, 450, 451, 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 7554, 1101, 120, 150, 1501, 1502, 1503, etc. manufactured by BASF Japan, an Ajisper) -PA111, PB711, PB821, PB822, PB824, etc. manufactured by fine technology company of taste element.
The surfactant may be exemplified by: anionic surfactants such as polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salts of styrene-acrylic acid copolymers, sodium alkyl naphthalene sulfonate, sodium alkyl diphenyl ether disulfonate, monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymers, or polyoxyethylene alkyl ether phosphate;
nonionic surfactants such as polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate, polyoxyethylene sorbitan monostearate, or polyethylene glycol monolaurate;
cationic surfactants such as alkyl quaternary ammonium salts or their ethylene oxide adducts; or alternatively
An amphoteric surfactant such as an alkyl betaine, e.g., an alkyl dimethylaminoacetic acid betaine, or an alkyl imidazoline. The other dispersing agent may be used alone or in combination of two or more.
The amount of the other dispersant to be used is preferably 0.1 to 40 parts by mass, more preferably 0.1 to 30 parts by mass, based on 100 parts by mass of the pigment. When the blending amount of the other dispersant is less than 0.1 mass%, the effect of addition is difficult to obtain, and when the blending amount is more than 40 mass%, the dispersion may be affected by the excessive dispersing auxiliary.
< pigment derivative >)
For the purpose of improving the dispersibility of the pigment, a pigment derivative may be used in the coloring composition as needed. The dye derivative is a compound having an acidic group, a basic group, a neutral group, or the like in an organic dye residue. Examples of the pigment derivative include: a compound having an acidic substituent such as a sulfo group, a carboxyl group, or a phosphate group (hereinafter, referred to as an acidic derivative), an amine salt of these, a compound having a basic substituent such as a sulfonamide group or a tertiary amino group at the end (hereinafter, referred to as a basic derivative), a compound having a neutral substituent such as a phenyl group or a phthalimidoalkyl group, or the like.
Examples of the organic coloring matter include: diketopyrrolopyrrole-based pigments, anthraquinone-based pigments, quinacridone-based pigments, dioxazine-based pigments, viol-cyclic ketone-based pigments, perylene-based pigments, thiazine indigo-based pigments, triazine-based pigments, benzimidazolone-based pigments, indole-based pigments such as benzisoindole, isoindoline-based pigments, isoindolinone-based pigments, quinophthalone-based pigments, naphthol-based pigments, vat-based pigments, metal complex-based pigments, azo-based pigments such as azo, disazo and polyazo-based pigments, and the like. Among these, basic derivatives are preferred.
In the coloring composition of the present invention, the amount of the alkali derivative to be blended is preferably 1 to 50 parts by mass, more preferably 3 to 30 parts by mass, and even more preferably 5 to 25 parts by mass, based on the mass of the pigment. When the pigment derivative having an alkaline group is 1% by mass or more, the effect of addition can be obtained, and when it is 50% by mass or less, the pigment dispersibility is improved, and the heat resistance and the light resistance are hardly adversely affected.
Specific examples of the pigment derivative having a basic group used in the present invention are given compound numbers and are shown below, but are not limited thereto.
Compound 1
General formula (27):
[ chemical 11]
Figure BDA0003964659340000201
Compound 2
General formula (28):
[ chemical 12]
Figure BDA0003964659340000202
Compound 3
General formula (29):
[ chemical 13]
Figure BDA0003964659340000203
Compound 4
General formula (30):
[ chemical 14]
Figure BDA0003964659340000211
/>
Compound 5
General formula (31):
[ 15]
Figure BDA0003964659340000212
< storage stabilizer >)
The coloring composition of the present invention may contain a storage stabilizer to stabilize the viscosity of the coloring composition with time.
Examples of the storage stabilizer include: quaternary ammonium chloride such as benzyl trimethyl ammonium chloride or diethyl hydroxy amine hydrochloride;
organic acids such as lactic acid and oxalic acid;
methyl esters of the organic acids;
Catechol such as t-butylcatechol;
organic phosphines such as tetraethylphosphine and tetraphenylphosphine; phosphite, and the like.
< color Filter >)
Next, the color filter of the present invention will be described.
The color filter of the present invention includes a filter segment or a black matrix formed of the coloring composition for a color filter of the present invention on a transparent substrate, and a general color filter includes at least one red filter segment, at least one green filter segment, and at least one blue filter segment. Or at least one magenta filter segment, at least one cyan filter segment, and at least one yellow filter segment.
The color filter of the present invention can be manufactured by forming filter segments of respective colors on a substrate using the coloring composition of the present invention by photolithography. Examples of the substrate include a glass plate having high transmittance to visible light, and a resin plate such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate.
The formation of each color filter by photolithography is performed by the following method.
The color composition for color filters is applied to a transparent substrate such as glass by a coating method such as spray coating, spin coating, slit coating, roll coating, or the like so that the dry film thickness is 0.2 μm to 10 μm, more preferably 0.2 μm to 5 μm. In drying the coating film, a vacuum dryer, a convection oven, an Infrared (IR) oven, a heating plate, or the like can be used. The film dried as needed is subjected to ultraviolet exposure through a mask having a prescribed pattern provided in a state of contact or non-contact with the film. Then, the color filter can be manufactured by immersing the color filter in a solvent or an alkaline developer, or spraying the developer by a sprayer or the like to remove the uncured portions and form a desired pattern.
Further, heating may be performed as needed in order to promote polymerization of the coloring composition for color filters. When the photolithography method is used, a color filter having higher accuracy than the printing method can be manufactured.
In the development, an aqueous solution of sodium carbonate, sodium hydroxide or the like can be used as the alkaline developing solution. Furthermore, organic bases such as dimethylbenzylamine and triethanolamine can be used. In addition, an antifoaming agent or a surfactant may be added to the developer.
If the black matrix is formed in advance before forming the respective color filter segments on the transparent substrate or the reflective substrate, the contrast ratio of the liquid crystal display panel can be further improved. As the black matrix, a multilayer film of chromium or chromium/chromium oxide, an inorganic film of titanium nitride or the like, or a resin film in which a light-shielding agent is dispersed may be used. In addition, a thin film transistor (Thin Film Transistor, TFT) may be formed in advance on the transparent substrate or the reflective substrate, and then a filter segment may be formed. By forming the optical filter section on the TFT substrate, the aperture ratio of the liquid crystal display panel can be improved, and the brightness of the light can be improved.
An overcoat film, a columnar spacer, a transparent conductive film, a liquid crystal alignment film, and the like are formed on the color filter of the present invention as necessary.
A color filter is bonded to a counter substrate by using a sealant, liquid crystal is injected from an injection port provided in a sealing portion, and then the injection port is sealed, and a polarizing film or a retardation film is bonded to the outside of the substrate as necessary, thereby manufacturing a liquid crystal display panel.
The liquid crystal display panel may be used in a liquid crystal display mode using color filters for colorization, such as Twisted Nematic (TN), super twisted nematic (super twisted nematic, STN), in-plane switching (IPS), vertical alignment (vertically alignment, VA), optically compensated bend (optically compensated bend, OCB), and the like.
< solid-state imaging element >)
The solid-state imaging element of the present invention includes the color filter of the present invention. The structure of the solid-state imaging device according to the present invention is not particularly limited, and examples thereof include the following structures.
The structure is as follows: the color filter for a solid-state imaging element of the present invention is provided on a substrate, the color filter having a plurality of photodiodes constituting a light receiving region of a solid-state imaging element (charge-coupled device (CCD) sensor, a complementary metal oxide semiconductor (complementary metal oxide semiconductor, CMOS) sensor, an organic CMOS sensor, or the like), and a transfer electrode including polysilicon or the like, the photodiodes and the transfer electrode having a light shielding film including tungsten or the like which is open only to a light receiving portion of the photodiodes, the light shielding film having a device protection film including silicon nitride or the like formed so as to cover the entire surface of the light shielding film and the light receiving portion of the photodiodes, and the device protection film.
Further, the device protection layer may have a structure in which a light condensing unit (for example, a microlens or the like; the same applies hereinafter) is provided below (on the side close to the substrate) the color filter, or a structure in which a light condensing unit is provided above the color filter.
The organic CMOS sensor is a hybrid structure of a double-layer structure including a full-color photosensitive organic photoelectric conversion film, which is a thin film of a photoelectric conversion layer, and a CMOS signal readout substrate, and has a function of capturing light by an organic material and converting the light into an electric signal, and a function of extracting the electric signal to the outside by an inorganic material, and in principle, the aperture ratio can be set to 100% with respect to incident light.
Since the organic photoelectric conversion film is a continuous film having a free structure and can be laid on the CMOS signal readout substrate, an expensive micromachining process is not required, and the organic photoelectric conversion film is suitable for miniaturization of the filter segment.
The arrangement of the color filter segments is not particularly limited, and known methods may be used.
Examples (example)
The present invention will be described below based on examples, but the present invention is not limited to the examples. The "parts" are "parts by mass" and "%" is "% by mass".
(weight average molecular weight (Mw) of resin)
The weight average molecular weight (Mw) of the resin was a weight average molecular weight (Mw) in terms of polystyrene measured using a gel permeation chromatograph (gel permeation chromatograph, GPC) (HLC-8120 GPC manufactured by Tosoh) and equipped with a Refractive Index (RI) detector using a TSKgel column (manufactured by Tosoh) and using Tetrahydrofuran (THF) as a developing solvent.
(acid value of resin)
To 0.5 to 1.0 parts of the resin solution, 80ml of acetone and 10ml of water were added and stirred to uniformly dissolve the mixture, and an aqueous solution of 0.1mol/L of potassium hydroxide (KOH) was used as a titration solution and titrated using an automatic titration apparatus ("COM-555" manufactured by Pingzhou Kogyo Co., ltd.) to measure the acid value of the resin solution. The acid value per unit nonvolatile component of the resin is calculated from the acid value of the resin solution and the nonvolatile component concentration of the resin solution.
The value of the dispersant in a dry state was determined by the following formula (mgKOH/g).
Acid value (mgKOH/g) = { (5.611. Alpha. Times.F)/S }/(nonvolatile matter concentration/100)
Wherein S: sample collection amount (g)
Alpha: consumption of 0.1mol/L Potassium hydroxide-ethanol solution (ml)
F: valence of 0.1mol/L potassium hydroxide-ethanol solution
(nonvolatile component of resin)
The mass of the sample was about 1 g under conditions for obtaining the nonvolatile components of the resin, and the drying conditions were 200℃for 10 minutes.
(production example of dispersant X1)
A reaction vessel including a gas introduction tube, a thermometer, a condenser, and a stirrer was charged with 50.0 parts of t-butyl acrylate, 50.0 parts of methyl methacrylate, and 25.0 parts of propylene glycol monomethyl ether acetate, and the mixture was replaced with nitrogen gas. The reaction vessel was heated to 50℃and 6.0 parts of 3-mercapto-1, 2-propanediol was added. The temperature was raised to 90℃and a solution prepared by dissolving 0.1 part of 2,2' -azobisisobutyronitrile in 45.7 parts of propylene glycol monomethyl ether acetate was added thereto to react for 10 hours. By the nonvolatile matter measurement, it was confirmed that 95% of the reaction occurred.
Next, 14.5 parts of pyromellitic dianhydride (produced by Daicel chemical industry Co., ltd.), 38.0 parts of PGMAc, and 0.2 parts of 1, 8-diazabicyclo- [5.4.0] -7-undecene as a catalyst were added and reacted at 120℃for 5 hours. Then, 12.1g of 3-methoxybutanol was added thereto, and the mixture was reacted at 120℃for 3 hours. By measurement of the acid value, it was confirmed that 98% or more of the acid anhydride was half-esterified, and the reaction was terminated. After the completion of the reaction, propylene glycol monomethyl ether acetate was added so that the nonvolatile content was 50 mass%, and a solution of dispersant X1 having an acid value of 95mgKOH/g and a weight average molecular weight of 9500 was obtained.
(production example of dispersants X2 to X14 and comparative dispersants Y1 to Y3)
The synthesis was performed in the same manner as in the production example of the dispersant X1 except that the raw materials and the amounts of the raw materials were used as described in table 1, to obtain solutions of the dispersants X2 to X14 and the comparative dispersants Y1 to Y3.
[ Table 1-1]
Figure BDA0003964659340000241
[ tables 1-2]
Figure BDA0003964659340000242
(preparation example of dispersant X15)
A reaction vessel including a gas introduction tube, a thermometer, a condenser, and a stirrer was charged with 6 parts of 3-mercapto-1, 2-propanediol, 14.5 parts of PMA, and 70.8 parts of propylene glycol monomethyl ether acetate, and the mixture was replaced with nitrogen gas. The reaction vessel was heated to 100℃and allowed to react for 5 hours. Then, 12.1g of 3-methoxybutanol was added thereto, and the mixture was reacted at 120℃for 3 hours. After the acid value was measured, it was confirmed that 98% or more of the acid anhydride was half-esterified, the temperature in the system was cooled to 70℃and 50.0 parts of t-butyl acrylate and 50.0 parts of methyl methacrylate were charged, and 38.0 parts of propylene glycol monomethyl ether acetate in which 0.1 part of 2,2' -azobisisobutyronitrile was dissolved was added and reacted for 10 hours. The polymerization was confirmed to have proceeded to 95% by the nonvolatile content measurement, and the reaction was terminated. After the completion of the reaction, propylene glycol monomethyl ether acetate was added so that the nonvolatile content was 50 mass%, and a solution of dispersant X15 having an acid value of 93mgKOH/g and a weight-average molecular weight of 10800 was obtained.
(preparation example of dispersant X16)
The synthesis was performed in the same manner as in the production example of dispersant X15 except that the raw materials and the amounts to be charged described in table 2 were used, and a solution of dispersant X16 was obtained.
TABLE 2
Figure BDA0003964659340000251
The materials used in the tables are listed below.
[ ethylenically unsaturated monomer ]
t-BA: acrylic acid tert-butyl ester
t-BMA: methacrylic acid tert-butyl ester
MMA: methyl methacrylate
EA: acrylic acid ethyl ester
MAA: methacrylic acid
[ Compounds having two hydroxyl groups and one thiol group in the molecule ]
Thioglycerol: 3-mercapto-1, 2-propanediol
[ free radical polymerization initiator ]
AIBN:2,2' -azobisisobutyronitrile
[ organic solvent ]
PGMAC: propylene glycol monomethyl ether acetate
3MB: 3-Methoxybutanol
PGME: propylene glycol monomethyl ether
DAA: diacetone alcohol
[ Tetracarboxylic dianhydride ]
PMA: pyromellitic dianhydride (Daicel chemical industry Co., ltd.)
[ esterification catalyst ]
DBU:1, 8-diazabicyclo- [5.4.0] -7-undecene (manufactured by Sanremo-Apro) Inc.)
Method for producing adhesive resin
(preparation of acrylic resin solution 1)
A reaction vessel equipped with a thermometer, a cooling tube, a nitrogen gas inlet tube and a stirrer was charged with 70.0 parts of propylene glycol monomethyl ether acetate, the temperature was raised to 80℃and the inside of the reaction vessel was replaced with nitrogen gas, and then a mixture of 13.3 parts of n-butyl methacrylate, 4.6 parts of 2-hydroxyethyl methacrylate, 4.3 parts of methacrylic acid, 7.4 parts of p-cumylphenol ethylene oxide modified acrylate ("methylene Luo Nisi (Aronix) M110" manufactured by Tokyo Co., ltd.) and 0.4 part of 2,2' -azobisisobutyronitrile was added dropwise from a dropping tube over 2 hours. After the completion of the dropwise addition, the reaction was further continued for 3 hours, whereby a solution of an acrylic resin having a weight-average molecular weight (Mw) of 26000 was obtained. After cooling to room temperature, about 2g of the resin solution was sampled, dried by heating at 180℃for 20 minutes, and the nonvolatile content was measured, and propylene glycol monoethyl ether acetate was added so that the nonvolatile content became 20 mass%, thereby preparing an acrylic resin solution 1.
Process for producing pigment dispersion
(production example of pigment Dispersion 1)
After the following mixture was stirred and mixed so as to be uniform, the mixture was dispersed for 3 hours by an Egger mill (eigermill) (Mini model M-250MKII manufactured by Eiger Japan) using zirconia beads having a diameter of 0.5mm, and then filtered by a filter having a pore size of 5.0 μm, whereby pigment dispersion 1 having a nonvolatile content of 20% by mass was produced.
PR254 (C.I. Pigment Red) 254 "Epaforubin (Irgaphor Red) B-CF", manufactured by BASF Japan Basf (Japan): 15.2 parts of
Basic derivative 1:0.8 part
Dispersant X1:8.0 parts of
Propylene glycol monomethyl ether acetate (PGMAc): 60.0 parts of
3-methoxybutanol (3 MB): 16.0 parts of
(production examples of pigment Dispersion 2 to pigment Dispersion 26)
Pigment dispersion 2 to pigment dispersion 26 were obtained in the same manner as in the production example of pigment dispersion 1, except that the raw materials and the amounts to be charged described in table 3 were used.
Basic derivative 1:
[ 16]
Figure BDA0003964659340000271
Basic derivative 2:
[ chemical 17]
Figure BDA0003964659340000272
Basic derivative 3:
[ chemical 18]
Figure BDA0003964659340000273
TABLE 3
Figure BDA0003964659340000281
Example 1
(photosensitive coloring composition 1)
The mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a filter having a pore size of 1 μm to prepare a photosensitive coloring composition 1.
Pigment dispersion 1:50.0 parts
Acrylic resin solution 1:7.5 parts
Photopolymerizable compound (manufactured by eastern asia synthesis company, "Luo Nisi (Aronix) M-402"): 2.0 parts
Photopolymerization initiator (IGM resin (IGM Resins), "ohmic nilrad (Omnirad 907)") manufactured by IGM Resins corporation: 1.2 parts of
Sensitizer (EAB-F manufactured by baogue chemical industries, inc.): 0.3 part
Propylene glycol monomethyl ether acetate (PGMAc): 39.0 parts
[ photopolymerizable Compound ]
Luo Nisi (Aronix) M-402: dipentaerythritol pentaacrylate/dipentaerythritol hexaacrylate (manufactured by east Asia synthetic chemical Co., ltd.)
[ photopolymerization initiator ]
Brilliant solid (Irgacure) OXE02: ethane-1-one, 1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ],1- (O-acetyl oxime) (manufactured by BASF Japan (Japan) Co., ltd.)
[ sensitizer ]
EAB-F:4,4' -bis (diethylamino) benzophenone (manufactured by Baotu chemical Co., ltd.)
Examples 2 to 21 and comparative examples 1 to 3
(production examples of photosensitive coloring composition 2 to photosensitive coloring composition 26)
Photosensitive coloring composition 2 to photosensitive coloring composition 26 were obtained in the same manner as in the production example of photosensitive coloring composition 1, except that the pigment dispersion described in table 4 was used instead of pigment dispersion 1 of example 1.
(viscosity stability)
The obtained photosensitive coloring composition was evaluated for viscosity stability by the following method. The initial viscosity of the photosensitive coloring composition after the preparation of the composition was measured at 25℃and 50rpm for the second day and the viscosity after the acceleration at 40℃for 1 week were measured using an E-type viscometer ("ELD-type viscometer" manufactured by Dong machine industries). From the values of the initial viscosity and the time-lapse viscosity, the time-lapse viscosity change rate was calculated by the following formula, and the viscosity stability was evaluated in 3 stages.
[ time viscosity change rate ] = | ([ initial viscosity ] - [ time viscosity ])/[ initial viscosity ] |100
O: the change rate is less than 5 percent (good)
Delta: the change rate is more than 5% and less than 10% (which can be practically used)
X: the change rate is more than 10 percent (bad)
(foreign matter evaluation)
The obtained photosensitive coloring composition was coated on a glass substrate having a black matrix formed in advance by spin coating, and then dried in a clean oven at 70 ℃ for 20 minutes. Next, the substrate was cooled to room temperature, and then, ultraviolet light exposure was performed using an ultra-high pressure mercury lamp via a photomask. Then, the substrate was subjected to spray development with a 23 ℃ aqueous solution of 0.2 mass% sodium carbonate for 30 seconds, and then washed with ion-exchanged water and dried. Further, a heat treatment was performed in a clean oven at 230 ℃ for 30 minutes to form a striped colored pixel layer on the substrate. After the heat treatment at 230℃of the produced colored pixel layer, the film thickness was adjusted to 2.0. Mu.m.
Using the obtained substrate, the number of foreign substances of the colored pixels was measured. The evaluation was performed by surface observation using a metal microscope "BX60" manufactured by Olympus systems inc. The magnification was 500 times, and the number of foreign matters that could be observed in any 5 fields of view during transmission was measured.
And (3) the following materials: the number of foreign matters is less than 3: excellent in
O: the number of foreign matters is 3 or more and less than 20: good quality
Delta: the number of foreign matters is 21 or more and less than 100: can be practically used
X: the number of foreign matters is 100 or more: failure of
(filterability)
As a method for evaluating the filterability, 60g of the obtained photosensitive coloring composition was subjected to a pressure of 0.05 MPa.s for a predetermined period of time by using a 1.5 μm disc filter Titan3 polytetrafluoroethylene filter (Titan 3 PTFEFILTER) manufactured by Tomsic Co., ltd. It can be said that the larger the liquid amount, the more excellent the filterability.
O: the amount of liquid passing through the filter was 45g or more (good)
Delta: the liquid amount passing through the filter is 30g or more and less than 45g (practical)
X: the amount of liquid passing through the filter is less than 30g (bad)
< PGMAc resolubility >)
The obtained photosensitive coloring composition was coated on a glass substrate by spin coating, prebaked at 100 ℃ for 3 minutes, and the resulting substrate was immersed in PGMAc, and the dissolved state was visually evaluated.
O: dissolution (good)
X: stripping (bad)
TABLE 4
Figure BDA0003964659340000301
As shown in table 4, the coloring compositions of the present invention using the dispersants X1 to X16 were excellent in storage stability, foreign matter inhibition on coating films, filterability, and PGMAc resolubility. In comparative example 1, since the molar ratio of the anhydride group to the hydroxyl group of the dispersant is less than 0.9, the number of anhydride residues in one molecule is reduced, adsorption to the pigment is insufficient, and viscosity stability is poor, thereby generating foreign matters. In comparative example 2, since the molar ratio of the anhydride group to the hydroxyl group exceeds 1.5, the viscosity stability is poor and the compatibility with the solvent is deteriorated. In comparative example 3, since water or alcohol was not used in the dispersant, the anhydride group at the end of the main chain remained, and thus the viscosity stability was poor and the filterability was also poor.

Claims (8)

1. A coloring composition comprising: a colorant comprising a pigment, a polyester dispersant and a solvent,
the polyester dispersant has a main chain based on an aromatic carboxylic acid ester site having an ester bond, which is a reaction formation site of an aromatic compound having two or more acid anhydride groups and a compound having two or more hydroxyl groups, and a side chain based on a vinyl polymer site, and
The acid anhydride group is 0.9 to 1.5 moles relative to 1 mole of the hydroxyl group,
the aromatic carboxylate moiety-based backbone has a seal moiety derived from a monol.
2. The coloring composition according to claim 1, wherein the monoalcohol is a compound having an ether group or a carbonyl group.
3. The coloring composition according to claim 1, wherein the polyester dispersant has a weight average molecular weight of 7000 to 25000.
4. A photosensitive coloring composition comprising: the coloring composition according to any one of claims 1 to 3, a photopolymerizable compound, and a photopolymerization initiator.
5. A color filter, comprising: a substrate, and a filter segment formed from the photosensitive coloring composition according to claim 4.
6. A solid-state imaging element comprising the color filter according to claim 5.
7. An image display device comprising the color filter of claim 5.
8. A process for producing a coloring composition comprising a colorant comprising a pigment, a polyester dispersant and a solvent, characterized in that,
the polyester dispersant has a main chain based on an aromatic carboxylic acid ester site having an ester bond, which is a reaction formation site of an aromatic compound having two or more acid anhydride groups and a compound having two or more hydroxyl groups, and a side chain based on a vinyl polymer site, and
The acid anhydride group is 0.9 to 1.5 moles relative to 1 mole of the hydroxyl group,
the aromatic carboxylate moiety-based backbone has a seal moiety derived from a monol.
CN202211490354.XA 2021-12-13 2022-11-25 Coloring composition, method for producing same, photosensitive coloring composition, color filter, solid-state imaging element, and image display device Pending CN116263562A (en)

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