WO2021192803A1 - 着色感光性組成物、硬化物、カラーフィルタ、固体撮像素子、及び、画像表示装置 - Google Patents

着色感光性組成物、硬化物、カラーフィルタ、固体撮像素子、及び、画像表示装置 Download PDF

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Publication number
WO2021192803A1
WO2021192803A1 PCT/JP2021/007209 JP2021007209W WO2021192803A1 WO 2021192803 A1 WO2021192803 A1 WO 2021192803A1 JP 2021007209 W JP2021007209 W JP 2021007209W WO 2021192803 A1 WO2021192803 A1 WO 2021192803A1
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Prior art keywords
group
compound
mass
resin
photosensitive composition
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PCT/JP2021/007209
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English (en)
French (fr)
Japanese (ja)
Inventor
明夫 水野
和也 尾田
翔一 中村
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Fujifilm Corp
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Fujifilm Corp
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Priority to KR1020227033192A priority Critical patent/KR20220146572A/ko
Priority to JP2022509439A priority patent/JPWO2021192803A1/ja
Publication of WO2021192803A1 publication Critical patent/WO2021192803A1/ja
Priority to US17/951,698 priority patent/US20230061680A1/en
Anticipated expiration legal-status Critical
Priority to JP2023196873A priority patent/JP2024014989A/ja
Priority to JP2024230827A priority patent/JP2025039598A/ja
Ceased legal-status Critical Current

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • 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
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10F—INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION
    • H10F39/00—Integrated devices, or assemblies of multiple devices, comprising at least one element covered by group H10F30/00, e.g. radiation detectors comprising photodiode arrays
    • H10F39/80—Constructional details of image sensors
    • H10F39/806—Optical elements or arrangements associated with the image sensors
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10F—INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION
    • H10F39/00—Integrated devices, or assemblies of multiple devices, comprising at least one element covered by group H10F30/00, e.g. radiation detectors comprising photodiode arrays
    • H10F39/80—Constructional details of image sensors
    • H10F39/805—Coatings
    • H10F39/8053—Colour filters

Definitions

  • the present disclosure relates to a colored photosensitive composition, a cured product, a color filter, a solid-state image sensor, and an image display device.
  • a color filter is an indispensable component of a solid-state image sensor or an image display device.
  • the solid-state image sensor and the image display device may generate noise due to the reflection of visible light. Therefore, a light-shielding film is provided on the solid-state image sensor or the image display device to suppress the generation of noise.
  • a colored photosensitive composition layer is formed by using a colored photosensitive composition containing a colorant, a polymerizable compound, a photopolymerization initiator, and an alkali-soluble resin.
  • a method of exposing and developing the colored photosensitive composition layer to form a pattern is known.
  • a conventional colored photosensitive composition the one described in Patent Document 1 is known.
  • Patent Document 1 Japanese Unexamined Patent Publication No. 2015-30781
  • An object to be solved by the embodiment according to the present disclosure is to provide a colored photosensitive composition having excellent development residue inhibitory properties.
  • Another problem to be solved by the embodiment according to the present disclosure is a cured product of the colored photosensitive composition, a color filter including the cured product, or a solid-state image sensor or an image display device including the color filter. Is to provide.
  • Means for solving the above problems include the following aspects.
  • a pigment, an amine compound having two or more cyclic amino groups in the molecule, a resin, and a photopolymerization initiator are contained, and the content of the pigment is higher than the total solid content in the colored photosensitive composition.
  • ⁇ 3> The colored photosensitive composition according to ⁇ 1> or ⁇ 2>, wherein the amine compound is a compound represented by the following formula 1.
  • X represents an n-valent organic group
  • L independently represents a single bond or a divalent linking group
  • R each independently represents a group having a cyclic amino group
  • n Represents an integer from 2 to 20.
  • ⁇ 4> The colored photosensitive composition according to any one of ⁇ 1> to ⁇ 3>, wherein the amine compound has a hindered amine structure as the cyclic amino group.
  • ⁇ 5> The colored photosensitive composition according to any one of ⁇ 1> to ⁇ 4>, wherein the amine compound is a compound having 3 to 8 cyclic amino groups in the molecule.
  • ⁇ 6> The colored photosensitive composition according to any one of ⁇ 1> to ⁇ 5>, wherein the amine compound is a compound having 4 to 8 cyclic amino groups in the molecule.
  • ⁇ 7> The colored photosensitive composition according to any one of ⁇ 1> to ⁇ 6>, wherein the photopolymerization initiator contains an oxime-based photopolymerization initiator.
  • ⁇ 10> A cured product obtained by curing the coloring curable composition according to any one of ⁇ 1> to ⁇ 9>.
  • ⁇ 11> A color filter comprising the cured product according to ⁇ 10>.
  • ⁇ 12> A solid-state image sensor having the color filter according to ⁇ 11>.
  • An image display device having the color filter according to ⁇ 11>.
  • a colored photosensitive composition having excellent development residue inhibitory properties is provided. Further, according to another embodiment according to the present disclosure, a cured product of the colored photosensitive composition, a color filter including the cured product, or a solid-state image sensor or an image display device including the color filter is provided. ..
  • the amount of each component in the composition is the total amount of the plurality of applicable substances present in the composition unless otherwise specified, when a plurality of substances corresponding to each component are present in the composition. Means.
  • the notation that does not describe substitution or non-substitution includes those having no substituent as well as those having a substituent.
  • the "alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
  • Me is a methyl group
  • Et is an ethyl group
  • Pr is a propyl group
  • Bu is a butyl group
  • Ph is a phenyl group, unless otherwise specified.
  • (meth) acrylic is a term used in a concept that includes both acrylic and methacryl
  • (meth) acryloyl is a term that is used as a concept that includes both acryloyl and methacryloyl. be.
  • the term "process” is included in this term as long as the intended purpose of the process is achieved, not only in an independent process but also in the case where it cannot be clearly distinguished from other processes. Is done.
  • the “total solid content” refers to the total mass of the components excluding the solvent from the total composition of the composition.
  • the “solid content” is a component excluding the solvent as described above, and may be, for example, a solid or a liquid at 25 ° C.
  • “% by mass” and “% by weight” are synonymous, and “parts by mass” and “parts by weight” are synonymous.
  • a combination of two or more preferred embodiments is a more preferred embodiment.
  • the weight average molecular weight (Mw) and the number average molecular weight (Mn) in the present disclosure use columns of TSKgel GMHxL, TSKgel G4000HxL, and TSKgel G2000HxL (all trade names manufactured by Toso Co., Ltd.). It is a molecular weight converted by detecting with a solvent THF (tetrahydrofuran) and a differential refractometer by a gel permeation chromatography (GPC) analyzer and using polystyrene as a standard substance.
  • THF tetrahydrofuran
  • GPC gel permeation chromatography
  • the term pigment means a compound that is difficult to dissolve in a solvent.
  • the term dye means a compound that is easily soluble in a solvent.
  • the colored photosensitive composition according to the present disclosure contains a pigment, an amine compound having two or more cyclic amino groups in the molecule, a resin, and a photopolymerization initiator, and the content of the pigment is the colored photosensitive composition. It is 40% by mass or more with respect to the total solid content in the medium.
  • the present inventors have made a developer in a conventional colored photosensitive composition in which the pigment content is 40% by mass or more with respect to the total solid content in the colored photosensitive composition. It has been found that the developer content is high insoluble in the pigment, which makes it difficult for the developer to permeate, and the amount of developable components is not small, so that development defects and development residues may be generated in large quantities.
  • the content of the pigment is 40% by mass or more with respect to the total solid content in the colored photosensitive composition, and the amine compound having two or more cyclic amino groups in the molecule is contained, as described above. Even in a colored photosensitive composition having a high pigment concentration, the amine compound is easily adsorbed on the surface of the pigment due to the cyclic structure of the amine, and is further coordinated with the amino group pigment having two or more of the amine compound.
  • the above resin interacts appropriately with the non-amino group to form a pigment particle-amine compound-resin structure, thereby suppressing adsorption and aggregation between the pigment particles contained in the colored photosensitive composition. Therefore, it is presumed that the developability is imparted and the development residue suppressing property is excellent.
  • the colored photosensitive composition according to the present disclosure contains an amine compound having two or more cyclic amino groups in the molecule.
  • the molecular weight of the amine compound having two or more cyclic amino groups in the molecule is the inhibitory property of developing residue, the stability of the dispersion liquid, and the adhesion of the obtained cured product (hereinafter, also simply referred to as "adhesion"). From the viewpoint, it is preferably 6,000 or less, more preferably 100 to 4,000, further preferably 200 to 3,000, and particularly preferably 500 to 2,500.
  • the cyclic amino group in the amine compound having two or more cyclic amino groups in the molecule may be a primary to tertiary cyclic amino group or a salt thereof, but it has a development residue inhibitory property and a dispersion. From the viewpoint of liquid stability and adhesion, a tertiary cyclic amino group or a salt thereof is preferable.
  • the counter anion of the salt that the cyclic amino group may form is not particularly limited, and may be a monovalent anion or a polyvalent anion. For example, a halide ion or water.
  • the cyclic amino group forms a salt, the cyclic amino group is preferably a protonated cation.
  • the cyclic amino group in the amine compound having two or more cyclic amino groups in the molecule is an aliphatic cyclic amino group such as a piperidino group or an aromatic cyclic amino group such as a pyridyl group. May be good.
  • the cyclic amino group in the amine compound having two or more cyclic amino groups in the molecule has a 5-membered ring or 6-membered ring structure from the viewpoint of developing residue inhibitory property, dispersion stability and adhesion. It is preferably a cyclic amino group, more preferably a cyclic amino group having a 6-membered ring structure, and even more preferably an aliphatic cyclic amino group having a 6-membered ring structure.
  • the amine compound having two or more cyclic amino groups in the molecule preferably has a hindered amine structure as the cyclic amino group from the viewpoint of development residue inhibitory property, dispersion stability and adhesion. It is particularly preferred to have a 6-membered ring hindered amine structure.
  • the hindered amine structure it is preferable that the two carbon atoms in the ring structure adjacent to the nitrogen atom of the cyclic amino group have a substituent such as an alkyl group.
  • Examples of the cyclic amino group having a hindered amine structure include a 1,2,2,6,6-pentamethylpiperidyl group, a 2,2,6,6-tetramethylpiperidyl group and a 1,2,6,6-trimethylpiperidyl group.
  • Group, 2,6-dimethylpiperidyl group, 1-methyl-2,6-di (t-butyl) piperidyl group, 2,6-di (t-butyl) piperidyl group, 1,2,2,5,5- Pentamethylpyrrolidyl group, 2,2,5,5-tetramethylpyrrolidyl group and the like are preferably mentioned.
  • 1,2,2,6,6-pentamethylpiperidyl group or 2,2,6,6-tetramethylpiperidyl group is preferable, and 1,2,2,6,6-pentamethylpiperidyl group is more preferable. preferable.
  • the number of cyclic amino groups in the amine compound having two or more cyclic amino groups in the molecule is preferably 2 to 20 from the viewpoint of development residue inhibitory property, dispersion stability, and adhesion. It is more preferably 2 to 8 pieces, further preferably 3 to 8 pieces, and particularly preferably 4 to 8 pieces.
  • the amine compound having two or more cyclic amino groups in the molecule is preferably a compound represented by the following formula 1 from the viewpoint of developing residue inhibitory property, dispersion stability, and adhesion.
  • X represents an n-valent organic group
  • L independently represents a single bond or a divalent linking group
  • R each independently represents a group having a cyclic amino group
  • n Represents an integer from 2 to 20.
  • X in Formula 1 is preferably an n-valent aliphatic group or a group having an n-valent aromatic ring or heteroaromatic ring. , N-valent aliphatic group is more preferable, and n-valent aliphatic hydrocarbon group which may have an ether bond and an ester bond is particularly preferable. Further, the molecular weight (formula amount) of X in the formula 1 is preferably 4,000 or less, and is 100 to 3,000, from the viewpoint of developing residue inhibitory property, dispersion liquid stability, and adhesion. Is more preferable, 200 to 2,500 is more preferable, and 200 to 2,000 is particularly preferable.
  • X in the formula 1 preferably has 4 to 400 carbon atoms (also referred to as “carbon atom number”), preferably 5 carbon atoms, from the viewpoint of developing residue inhibitory property, dispersion stability, and adhesion. It is more preferably from to 200, and particularly preferably from 8 to 150 carbon atoms.
  • Each of L in the formula 1 is preferably a single bond, an ether bond, or an ester bond, and more preferably an ether bond or an ester bond.
  • R in the formula 1 is preferably a cyclic amino group or a group in which an alkylene group is bonded to a cyclic amino group, and more preferably a cyclic amino group.
  • N in Equation 1 is preferably an integer of 2 to 8, more preferably an integer of 3 to 8, and particularly preferably an integer of 4 to 8.
  • X include, for example, an alkylene group having 4 to 12 carbon atoms, a group shown below, and the like.
  • Wavy line portion represents a bonding position as L, the double wavy line portion respectively, represents a bonding position to any of the structures shown in both sides of the L AH.
  • nAH is preferably an integer of 1 to 3, and more preferably 1 or 2.
  • amine compound having two or more cyclic amino groups in the molecule are shown, but the present disclosure is not limited to this.
  • the wavy line portion in the following compound represents the bonding position with the corresponding other structure.
  • ADEKA STAB LA-52 Tetrakis (1,2,2,6,6-pentamethyl-4-piperidyl) butane-1, 2,3,4-tetracarboxylate
  • ADEKA STAB LA-57 Tetrakis (2,2,6,6-tetramethyl-4-piperidyl) butane-1,2,3,4-tetracarboxylate
  • LA-63P (1,2) , 3,4-Butanetetracarboxylic acid, tetramethylester, reaction products with 1,2,2,6,6-pentamethyl-4-piperidinol and ⁇ , ⁇ , ⁇ ', ⁇ '-tetramethyl-2,4,8,10- tetraoxaspiro [5.5] undecane-3,9-diethanol)
  • ADEKA STAB LA-68 (1,2,3,4-Butanetetracarboxylic acid, te
  • the colored photosensitive composition according to the present disclosure may contain one or more amine compounds having two or more cyclic amino groups in the molecule, or may contain two or more.
  • the content of the amine compound having two or more cyclic amino groups in the molecule in the colored photosensitive composition according to the present disclosure is colored photosensitive from the viewpoints of development residue inhibitory property, dispersion stability, and adhesion. It is preferably 0.05% by mass to 20% by mass, more preferably 1% by mass to 16% by mass, and 2% by mass to 10% by mass with respect to the total solid content of the composition. Especially preferable.
  • the colored photosensitive composition according to the present disclosure contains a pigment.
  • the pigment may be either an inorganic pigment or an organic pigment, but is preferably an organic pigment.
  • an inorganic pigment or a material in which a part of the organic-inorganic pigment is replaced with an organic chromophore can be used. Hue design can be facilitated by replacing inorganic pigments and organic-inorganic pigments with organic chromophores.
  • the colored photosensitive composition according to the present disclosure can be preferably used as a colored photosensitive composition for forming colored pixels in a color filter.
  • Examples of the colored pixel include a red pixel, a green pixel, a blue pixel, a magenta color pixel, a cyan color pixel, a yellow color pixel, and the like. Among them, green pixels are preferably mentioned.
  • the average primary particle size of the pigment is preferably 1 nm to 200 nm.
  • the lower limit is preferably 5 nm or more, more preferably 10 nm or more.
  • the upper limit is preferably 180 nm or less, more preferably 150 nm or less, and even more preferably 100 nm or less.
  • the primary particle size of the pigment can be determined from an image photograph obtained by observing the primary particles of the pigment with a transmission electron microscope. Specifically, the projected area of the primary particles of the pigment is obtained, and the corresponding circle-equivalent diameter is calculated as the primary particle diameter of the pigment.
  • the average primary particle size in the present disclosure is an arithmetic mean value of the primary particle size for the primary particles of 400 pigments.
  • the primary particles of the pigment refer to independent particles without agglomeration.
  • the amount of the pigment dissolved in 100 g of propylene glycol methyl ether acetate at 25 ° C. is preferably less than 0.01 g, more preferably less than 0.005 g, and even more preferably less than 0.001 g.
  • Organic pigments include phthalocyanine pigments, dioxazine pigments, quinacridone pigments, anthraquinone pigments, perylene pigments, azo pigments, diketopyrrolopyrrole pigments, pyrolopyrrole pigments, isoindolin pigments, quinophthalone pigments, triarylmethane pigments, xanthene pigments, and methine pigments. , Kinolin pigments and the like. Specific examples of the organic pigment include those shown below.
  • the colored photosensitive composition according to the present disclosure preferably contains a green pigment as a pigment, and more preferably contains a green pigment and a yellow pigment, from the viewpoint of more exerting the effects in the present disclosure.
  • the pigment preferably contains a phthalocyanine pigment, and more preferably contains a green phthalocyanine pigment, from the viewpoint of sensitivity and spectral characteristics.
  • the green pigment known ones can be used.
  • phthalocyanine compounds such as Color Index (CI) Pigment Green 7, 10, 36, 37, 58, 59, 62, 63 can be mentioned.
  • a green pigment a halogen having an average of 10 to 14 halogen atoms in one molecule, an average of 8 to 12 bromine atoms, and an average of 2 to 5 chlorine atoms.
  • a zinc phthalocyanine compound can also be used.
  • the compound described in International Publication No. 2015/118720, the compound described in China Patent Application Publication No. 1069090227, a phthalocyanine compound having a phosphate ester as a ligand, and the like can also be used.
  • the green pigment described in JP-A-2019-8014 or JP-A-2018-180023 may be used.
  • the green pigment easily forms a film having spectral characteristics suitable for green pixels, and therefore, C.I. I. Pigment Green 58 and C.I. I. It preferably contains at least one compound selected from the group consisting of Pigment Green 36, C.I. I. It is more preferable to include Pigment Green 58.
  • the green pigment may be used alone or in combination of two or more.
  • the content of the green pigment in the total solid content of the colored photosensitive composition is preferably 10% by mass to 80% by mass.
  • the lower limit is more preferably 15% by mass or more, and particularly preferably 20% by mass or more.
  • the upper limit is more preferably 70% by mass or less, and particularly preferably 60% by mass or less.
  • yellow pigment examples include azo compounds, quinophthalone compounds, isoindolinone compounds, isoindoline compounds, anthraquinone compounds and the like. Of these, an isoindoline compound is preferable because it is easy to form a film having spectral characteristics suitable for green pixels.
  • the color index (CI) Pigment Yellow (hereinafter, also simply referred to as “PY”) 1,2,3,4,5,6,10,11,12,13,14,15, 16,17,18,20,24,31,32,34,35,35: 1,36,36: 1,37,37: 1,40,42,43,53,55,60,61,62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118,119,120,123,125,126,127,128,129,137,138,139,147,148,150,151,152,153,154,155,156,161,162,164,166 167,168,169,170,171,172,173,174,175,176,177,179,180,181,182,185,187,188,193,194,
  • the pigment described in JP-A-2017-201003 and the pigment described in JP-A-2017-197719 can be used.
  • the yellow pigment at least one anion selected from the group consisting of an azo compound represented by the following formula (Y) and an azo compound having a tautomeric structure thereof, two or more kinds of metal ions, and a melamine compound.
  • Y an azo compound represented by the following formula (Y)
  • azo compound having a tautomeric structure thereof two or more kinds of metal ions
  • a melamine compound a metal azo pigment containing the above can also be used.
  • RY1 and RY2 independently represent -OH or -NR Y5 RY6
  • Y7 independently represents a hydrogen atom or an alkyl group.
  • the number of carbon atoms of the alkyl group represented by RY5 to RY7 is preferably 1 to 10, more preferably 1 to 6, and even more preferably 1 to 4.
  • the alkyl group may be linear, branched or cyclic, preferably linear or branched, and more preferably linear.
  • the alkyl group may have a substituent. Preferred examples of the substituent include a halogen atom, a hydroxy group, an alkoxy group, a cyano group and an amino group.
  • paragraphs 0011 to 0062, 0137 to 0276 of JP-A-2017-171912, paragraphs 0010 to 0062, 0138-0295, JP-A-2017-171914 of JP-A-2017-171913, and JP-A-2017-171914 paragraphs 0011 to 0062, 0139 to 0190, and paragraphs 0010 to 0065 and 0142 to 0222 of JP-A-2017-171915 can be referred to, and these contents are incorporated in the present specification.
  • a quinophthalone dimer represented by the following formula (Q) can also be preferably used.
  • the quinophthalone dimer described in Japanese Patent No. 6443711 can also be preferably used.
  • X 1 to X 16 independently represent a hydrogen atom or a halogen atom, and Z represents an alkylene group having 1 to 3 carbon atoms.
  • Examples of the yellow pigment include JP-A-2018-2013798, JP-A-2018-62578, Patent No. 6432077, Patent No. 6432076, JP-A-2018-155881, JP-A-2018-11757, and JP-A. 2018-40835, 2017-197640, 2016-145282, 2014-85565, 2014-21139, 2013-209614, 2013- 209435, 2013-181015, 2013-61622, 2013-54339, 2013-32486, 2012-226110, 2008-74987 Japanese Patent Application Laid-Open No. 2008-81565, Japanese Patent Application Laid-Open No. 2008-79486, Japanese Patent Application Laid-Open No. 2008-74985, Japanese Patent Application Laid-Open No. 2008-50420, Japanese Patent Application Laid-Open No. 2008-31281, or Japanese Patent Application Laid-Open No. 48-32765.
  • the quinophthalone pigments described in the publication can also be preferably used.
  • the yellow pigment the quinophthalone compounds described in paragraphs 0011 to 0034 of JP2013-54339, the quinophthalone compounds described in paragraphs 0013 to 0058 of JP2014-26228, and JP-A-2019-8014.
  • the compound described in Japanese Patent Application Laid-Open No. 6607427, the compound described in Japanese Patent Publication No. 6607427, and the like can also be used.
  • the compound described in JP-A-2018-62644 can also be used. This compound can also be used as a pigment derivative. Further, as described in Japanese Patent Application Laid-Open No. 2018-155881, C.I. I. Pigment Yellow 129 may be added for the purpose of improving weather resistance.
  • red pigments diketopyrrolopyrrole compounds in which at least one bromine atom is substituted in the structure described in JP-A-2017-2013384, diketopyrrolopyrrole compounds described in paragraphs 0016 to 0022 of Patent No. 6248838, international The diketopyrrolopyrrole compound described in Publication No. 2012/102399, the diketopyrrolopyrrole compound described in International Publication No. 2012/117956, the naphthol azo compound described in JP-A-2012-229344, Japanese Patent No. 6516119. , The red pigment described in Japanese Patent No. 6525101, and the like can also be used.
  • red pigment a compound having a structure in which an aromatic ring group having an oxygen atom, a sulfur atom or a nitrogen atom bonded to the aromatic ring is bonded to a diketopyrrolopyrrole skeleton can also be used. can.
  • an aluminum phthalocyanine compound having a phosphorus atom can also be used. Specific examples include the compounds described in paragraphs 0022 to 0030 of JP2012-247591A and paragraphs 0047 of JP2011-157478A.
  • White pigments include titanium oxide, strontium titanate, barium titanate, zinc oxide, magnesium oxide, zirconium oxide, aluminum oxide, barium sulfate, silica, talc, mica, aluminum hydroxide, calcium silicate, aluminum silicate, hollow. Examples include resin particles and zinc sulfide.
  • the white pigment is preferably particles having a titanium atom, and more preferably titanium oxide. Further, the white pigment is preferably particles having a refractive index of 2.10 or more with respect to light having a wavelength of 589 nm. The above-mentioned refractive index is preferably 2.10 to 3.00, and more preferably 2.50 to 2.75.
  • titanium oxide described in "Titanium Oxide Physical Properties and Applied Technology, by Manabu Kiyono, pp. 13-45, published on June 25, 1991, published by Gihodo Publishing" can also be used.
  • the white pigment is not limited to a single inorganic substance, but particles compounded with other materials may be used. For example, particles having pores or other materials inside, particles in which a large number of inorganic particles are attached to core particles, core particles composed of core particles composed of polymer particles, and shell composite particles composed of a shell layer composed of inorganic nanoparticles are used. Is preferable.
  • the core and shell composite particles composed of the core particles composed of the polymer particles and the shell layer composed of the inorganic nanoparticles for example, the description in paragraphs 0012 to 0042 of JP2015-047520 can be referred to. The content is incorporated herein by reference.
  • Hollow inorganic particles can also be used as the white pigment.
  • Hollow inorganic particles are inorganic particles having a structure having cavities inside, and are inorganic particles having cavities surrounded by an outer shell.
  • Examples of the hollow inorganic particles include the hollow inorganic particles described in JP-A-2011-075786, International Publication No. 2013/061621, JP-A-2015-164881, and the like, and the contents thereof are incorporated in the present specification. Is done.
  • the black pigment is not particularly limited, and known ones can be used.
  • carbon black, titanium black, graphite and the like can be mentioned, with carbon black and titanium black being preferable, and titanium black being more preferable.
  • Titanium black is black particles containing a titanium atom, and low-order titanium oxide or titanium oxynitride is preferable.
  • the surface of titanium black can be modified as needed for the purpose of improving dispersibility and suppressing cohesion.
  • Titanium black preferably has a small primary particle size and an average primary particle size of each particle. Specifically, the average primary particle size is preferably 10 to 45 nm. Titanium black can also be used as a dispersion. For example, a dispersion containing titanium black particles and silica particles and having a content ratio of Si atoms and Ti atoms in the dispersion adjusted to a range of 0.20 to 0.50 can be mentioned. Regarding the above dispersion, the description in paragraphs 0020 to 0105 of JP2012-169556A can be referred to, and the content thereof is incorporated in the present specification.
  • CI Color Index
  • Titanium black preferably has a small primary particle size and an average primary particle size of each particle. Specifically, the average primary particle size is preferably 10 to 45 nm. Titanium black can also be used as a dispersion. For example, a dispersion containing titanium black particles and silica particles and having a content ratio of Si atoms and Ti atoms in the dispersion
  • titanium black products examples include titanium black 10S, 12S, 13R, 13M, 13MC, 13RN, 13MT (trade name: manufactured by Mitsubishi Materials Corporation), Tilak D (trade name: manufactured by Mitsubishi Materials Corporation). Product name: Ako Kasei Co., Ltd.) and the like.
  • a pigment having an X-ray diffraction pattern by a specific CuK ⁇ ray is preferably mentioned.
  • the phthalocyanine pigment described in Japanese Patent No. 6561862 the diketopyrrolopyrrole pigment described in Japanese Patent No. 6413872, and the azo pigment described in Japanese Patent No. 6281345 (CI Pigment Red269). And so on.
  • the colored photosensitive composition according to the present disclosure may contain one kind of pigment alone or two or more kinds of pigments.
  • the content of the pigment is 40% by mass or more with respect to the total solid content in the colored photosensitive composition, and is 45% by mass or more from the viewpoint of development residue inhibitory property, dispersion liquid stability, and adhesion. It is preferable, 50% by mass or more is more preferable, and 60% by mass or more is particularly preferable. Further, the upper limit is preferably 80% by mass or less.
  • the colored photosensitive composition according to the present disclosure contains a resin.
  • the resin is blended, for example, for the purpose of dispersing particles such as pigments in a colored photosensitive composition and for the purpose of a binder.
  • a resin mainly used for dispersing particles such as pigments is also referred to as a dispersant.
  • such an application of the resin is an example, and it can be used for a purpose other than such an application.
  • the weight average molecular weight (Mw) of the resin is preferably 3,000 to 2,000,000.
  • the upper limit is more preferably 1,000,000 or less, and particularly preferably 500,000 or less.
  • the lower limit is more preferably 4,000 or more, and particularly preferably 5,000 or more.
  • the resin examples include (meth) acrylic resin, en-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, polyimide resin, and polyamideimide resin. , Polyolefin resin, cyclic olefin resin, polyester resin, styrene resin and the like. One of these resins may be used alone, or two or more thereof may be mixed and used.
  • the resin described in JP-A-2017-032685, the resin described in JP-A-2017-075248, and the resin described in JP-A-2017-066240 can also be used.
  • the colored photosensitive composition according to the present disclosure preferably contains a resin having an acid group as the resin.
  • the developability of the colored photosensitive composition can be improved, pixels having excellent rectangularity can be easily formed, and by interacting with the amine compound, it is suitable as a dispersant. It works and is better at dispersibility of pigments.
  • the acid group include a carboxy group, a phosphoric acid group, a sulfo group, a phenolic hydroxy group and the like, and a carboxy group is preferable.
  • the resin having an acid group can be used as, for example, an alkali-soluble resin.
  • the resin having an acid group preferably contains a repeating unit having an acid group in the side chain, and more preferably contains 5 mol% to 70 mol% of the repeating unit having an acid group in the side chain in all the repeating units of the resin. ..
  • the upper limit of the content of the repeating unit having an acid group in the side chain is preferably 50 mol% or less, more preferably 30 mol% or less.
  • the lower limit of the content of the repeating unit having an acid group in the side chain is preferably 10 mol% or more, and more preferably 20 mol% or more.
  • the resin having an acid group consists of a group consisting of a compound represented by the following formula (ED1) and a compound represented by the following formula (ED2) (hereinafter, these compounds may be referred to as “ether dimers”). It is also preferable to include a repeating unit derived from a monomer component containing at least one selected monomer.
  • R 1 and R 2 each independently represent a hydrocarbon group having 1 to 25 carbon atoms which may have a hydrogen atom or a substituent.
  • R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms.
  • the description in JP-A-2010-168539 can be referred to, and the contents thereof are incorporated in the present specification.
  • the description in paragraph 0317 of Japanese Patent Application Laid-Open No. 2013-209760 can be referred to, and this content is incorporated in the present specification.
  • the resin used in the present disclosure preferably contains a repeating unit derived from the compound represented by the following formula (X).
  • R 1 represents a hydrogen atom or a methyl group
  • R 2 represents an alkylene group having 2 to 10 carbon atoms
  • R 3 represents a hydrogen atom or a benzene ring having 1 to 20 carbon atoms.
  • n represents an integer from 1 to 15.
  • the acid value of the resin having an acid group is preferably 30 mgKOH / g to 500 mgKOH / g.
  • the lower limit is more preferably 40 mgKOH / g or more, and particularly preferably 50 mgKOH / g or more.
  • the upper limit is more preferably 400 mgKOH / g or less, further preferably 300 mgKOH / g or less, and particularly preferably 200 mgKOH / g or less.
  • the weight average molecular weight (Mw) of the resin having an acid group is preferably 5,000 to 100,000.
  • the number average molecular weight (Mn) of the resin having an acid group is preferably 1,000 to 20,000.
  • the method for introducing the acidic functional group into the resin is not particularly limited, and examples thereof include the method described in Japanese Patent No. 6349629. Further, as a method for introducing an acidic functional group into the resin, in a dispersant (particularly a dispersant having an ethylenically unsaturated group) or an alkali-soluble resin, an acid anhydride is added to the hydroxy group generated by the ring opening reaction of the epoxy group. There is also a method of introducing an acid group by reacting.
  • a resin having a basic group as the resin.
  • the developability of the colored photosensitive composition can be improved, and it is easy to form pixels having excellent rectangularity.
  • the basic group include an amino group and a heteroaryl group having a nitrogen atom, and an amino group is preferable, and a tertiary amino group is more preferable.
  • a resin having a basic group can be used as, for example, an alkali-soluble resin.
  • the amine value of the resin having an amino group as a basic group is preferably 30 mgKOH / g to 200 mgKOH / g.
  • the lower limit is more preferably 40 mgKOH / g or more, and particularly preferably 50 mgKOH / g or more.
  • the upper limit is more preferably 250 mgKOH / g or less, further preferably 200 mgKOH / g or less, and particularly preferably 150 mgKOH / g or less.
  • the weight average molecular weight (Mw) of the resin having an amino group is preferably 5,000 to 100,000.
  • the number average molecular weight (Mn) of the resin having an amino group is preferably 1,000 to 20,000.
  • the colored photosensitive composition according to the present disclosure may also contain a resin as a dispersant.
  • the dispersant include an acidic dispersant (acidic resin) and a basic dispersant (basic resin).
  • the acidic dispersant (acidic resin) represents a resin in which the amount of acid groups is larger than the amount of basic groups.
  • the acidic dispersant (acidic resin) is preferably a resin in which the amount of acid groups accounts for 70 mol% or more when the total amount of the amount of acid groups and the amount of basic groups is 100 mol%, and is substantially an acid. A resin consisting only of groups is more preferable.
  • the acid group of the acidic dispersant (acidic resin) is preferably a carboxy group.
  • the acid value of the acidic dispersant is preferably 40 mgKOH / g to 105 mgKOH / g, more preferably 50 mgKOH / g to 105 mgKOH / g, and even more preferably 60 mgKOH / g to 105 mgKOH / g.
  • the basic dispersant represents a resin in which the amount of basic groups is larger than the amount of acid groups.
  • the basic dispersant (basic resin) is preferably a resin in which the amount of basic groups exceeds 50 mol% when the total amount of the amount of acid groups and the amount of basic groups is 100 mol%.
  • the basic group contained in the basic dispersant is preferably an amino group.
  • the resin used as the dispersant preferably contains a repeating unit having an acid group. Since the resin used as the dispersant contains a repeating unit having an acid group, it is possible to further suppress the generation of development residue when forming a pattern by the photolithography method.
  • the resin used as the dispersant is also preferably a graft resin.
  • graft resin the description in paragraphs 0025 to 0094 of JP2012-255128A can be referred to, and the content thereof is incorporated in the present specification.
  • the resin used as the dispersant is also preferably a polyimine-based dispersant containing a nitrogen atom in at least one of the main chain and the side chain.
  • the polyimine-based dispersant has a main chain having a partial structure having a functional group of pKa14 or less and a side chain having 40 to 10,000 atoms, and basic nitrogen is contained in at least one of the main chain and the side chain.
  • a resin having an atom is preferable.
  • the basic nitrogen atom is not particularly limited as long as it is a nitrogen atom exhibiting basicity.
  • the description in paragraphs 0102 to 0166 of JP2012-255128A can be referred to, and the content thereof is incorporated in the present specification.
  • the resin used as the dispersant is a resin having a structure in which a plurality of polymer chains are bonded to the core portion.
  • a resin include dendrimers (including star-shaped polymers).
  • specific examples of the dendrimer include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP2013-043962.
  • alkali-soluble resin can also be used as a dispersant.
  • the resin used as the dispersant is a resin containing a repeating unit having an ethylenically unsaturated group in the side chain.
  • the content of the repeating unit having an ethylenically unsaturated group in the side chain is preferably 10 mol% or more, more preferably 10 mol% to 80 mol%, and 20 mol% in all the repeating units of the resin. It is more preferably ⁇ 70 mol%.
  • a resin having an aromatic carboxy group (hereinafter, “resin B”) is preferably mentioned.
  • the aromatic carboxy group may be contained in the main chain of the repeating unit or may be contained in the side chain of the repeating unit.
  • the aromatic carboxy group is preferably contained in the main chain of the repeating unit because of its excellent developability and color loss. Details are unknown, but it is speculated that the presence of aromatic carboxy groups near the main chain will further improve these properties.
  • an aromatic carboxyl group is a group having a structure in which one or more carboxyl groups are bonded to an aromatic ring.
  • the number of carboxy groups bonded to the aromatic ring is preferably 1 to 4, and more preferably 1 to 2.
  • the resin B used in the present disclosure is preferably a resin containing at least one repeating unit selected from the repeating unit represented by the formula (b-1) and the repeating unit represented by the formula (b-10). ..
  • Ar 1 represents a group containing an aromatic carboxyl group
  • L 1 represents -COO- or -CONH-
  • L 2 represents a divalent linking group
  • Ar 10 represents a group containing an aromatic carboxyl group
  • L 11 represents -COO- or -CONH-
  • L 12 represents a trivalent linking group
  • P 10 is a polymer. Represents a chain.
  • Examples of the group containing an aromatic carboxy group represented by Ar 1 in the formula (b-1) include a structure derived from an aromatic tricarboxylic acid anhydride, a structure derived from an aromatic tetracarboxylic acid anhydride, and the like.
  • Examples of the aromatic tricarboxylic acid anhydride and the aromatic tetracarboxylic acid anhydride include compounds having the following structures.
  • Q 1 is represented by a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2- , -C (CF 3 ) 2- , and the following formula (Q-1). Represents a group to be used or a group represented by the following formula (Q-2).
  • aromatic tricarboxylic acid anhydrides include benzenetricarboxylic acid anhydrides (1,2,3-benzenetricarboxylic acid anhydrides, trimellitic acid anhydrides [1,2,4-benzenetricarboxylic acid anhydrides], etc.).
  • Naphthalenetricarboxylic acid anhydride (1,2,4-naphthalenetricarboxylic acid anhydride, 1,4,5-naphthalenetricarboxylic acid anhydride, 2,3,6-naphthalenetricarboxylic acid anhydride, 1,2,8-naphthalene Tricarboxylic acid anhydride, etc.), 3,4,4'-benzophenone tricarboxylic acid anhydride, 3,4,4'-biphenyl ether tricarboxylic acid anhydride, 3,4,4'-biphenyl tricarboxylic acid anhydride, 2,3 , 2'-biphenyltricarboxylic acid anhydride, 3,4,4'-biphenylmethanetricarboxylic acid anhydride, or 3,4,4'-biphenylsulfonetricarboxylic acid anhydride.
  • aromatic tetracarboxylic acid anhydrides include pyromellitic dianhydride, ethylene glycol dianhydride trimellitic acid ester, propylene glycol dianhydride trimellitic acid ester, butylene glycol dianhydride trimellitic acid ester, 3,3.
  • Specific examples of the group containing an aromatic carboxyl group represented by Ar 1 include a group represented by the formula (Ar-1), a group represented by the formula (Ar-2), and a group represented by the formula (Ar-3). Examples include the base.
  • n1 represents an integer of 1 to 4, preferably an integer of 1 to 2, and more preferably 2.
  • n2 represents an integer of 1 to 8, preferably an integer of 1 to 4, more preferably 1 to 2, and even more preferably 2.
  • n3 and n4 each independently represent an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1 to 2, and preferably 1. More preferred. However, at least one of n3 and n4 is an integer of 1 or more.
  • Q 1 is a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2- , -C (CF 3 ) 2- , the above formula (Q-). It represents a group represented by 1) or a group represented by the above formula (Q-2).
  • L 1 represents -COO- or -CONH-, and preferably -COO-.
  • the divalent linking group represented by L 2 in the formula (b-1) includes an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S- and these.
  • a group that combines two or more of the above can be mentioned.
  • the alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 1 to 15 carbon atoms.
  • the alkylene group may be linear, branched, or cyclic.
  • the arylene group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 10 carbon atoms.
  • the alkylene group and the arylene group may have a substituent.
  • substituent include a hydroxy group and the like.
  • the divalent linking group L 2 represents is preferably a group represented by -O-L 2a -O-.
  • L 2a is an alkylene group; an arylene group; a group in which an alkylene group and an arylene group are combined; at least one selected from an alkylene group and an arylene group, and —O—, ⁇ CO ⁇ , ⁇ COO ⁇ , ⁇ OCO ⁇ ,. Examples thereof include a group in which at least one selected from the group consisting of -NH- and -S- is combined.
  • the alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 1 to 15 carbon atoms.
  • the alkylene group may be linear, branched or cyclic.
  • the alkylene group and the arylene group may have a substituent. Examples of the substituent include a hydroxy group and the like.
  • the group containing the aromatic carboxy group represented by Ar 10 in the formula (b-10) has the same meaning as Ar 1 in the formula (b-1), and the preferable range is also the same.
  • L 11 represents -COO- or -CONH-, and preferably -COO-.
  • the trivalent linking group represented by L 12 in the formula (b-10) includes a hydrocarbon group, -O-, -CO-, -COO-, -OCO-, -NH-, -S- and two of these. Groups that combine species and above can be mentioned.
  • the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group.
  • the number of carbon atoms of the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15.
  • the aliphatic hydrocarbon group may be linear, branched or cyclic.
  • the number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 10.
  • the hydrocarbon group may have a substituent. Examples of the substituent include a hydroxy group and the like.
  • the trivalent linking group represented by L 12 is preferably a group represented by the following formula (L12-1), and more preferably a group represented by the formula (
  • L 12a and L 12b each independently represent a trivalent linking group
  • X 1 represents S
  • * 1 represents the bonding position with L 11 in the formula (b-10)
  • * 2 represents the bonding position with L 11 in the formula (b-10). It represents a bonding position to P 10 -10).
  • the trivalent linking group represented by L 12a and L 12b is a group consisting of a hydrocarbon group; a hydrocarbon group and -O-, -CO-, -COO-, -OCO-, -NH- and -S-.
  • a group that is a combination of at least one selected from the above can be mentioned.
  • P 10 represents a polymer chain.
  • the polymer chain represented by P 10 preferably has at least one repeating unit selected from poly (meth) acrylic repeating units, polyether repeating units, polyester repeating units and polyol repeating units.
  • the weight average molecular weight of the polymer chain P 10 is preferably 500 to 20,000.
  • the lower limit is more preferably 500 or more, and particularly preferably 1,000 or more.
  • the upper limit is more preferably 10,000 or less, further preferably 5,000 or less, and particularly preferably 3,000 or less.
  • the resin B is a resin having a repeating unit represented by the formula (b-10)
  • the resin B is preferably used as a dispersant.
  • the polymer chain represented by P 10 is preferably a polymer chain containing a repeating unit represented by the following formulas (P-1) to (P-5), and is preferably a polymer chain containing a repeating unit represented by the following formulas (P-1) to (P-5). It is more preferable that the polymer chain contains the repeating unit represented by 5).
  • RP1 and RP2 each represent an alkylene group.
  • the alkylene group represented by RP1 and RP2 a linear or branched alkylene group having 1 to 20 carbon atoms is preferable, and a linear or branched alkylene group having 2 to 16 carbon atoms is more preferable. , A linear or branched alkylene group having 3 to 12 carbon atoms is more preferable.
  • RP3 represents a hydrogen atom or a methyl group.
  • L P1 represents a single bond or an arylene group
  • L P2 represents a single bond or a divalent linking group.
  • L P1 is preferably a single bond.
  • Examples of the divalent linking group represented by LP2 include an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, and -SO-.
  • RP4 represents a hydrogen atom or a substituent.
  • Substituents include hydroxy groups, carboxy groups, alkyl groups, aryl groups, heteroaryl groups, alkoxy groups, aryloxy groups, heteroaryloxy groups, alkylthioether groups, arylthioether groups, heteroarylthioether groups, and (meth) acryloyl.
  • Examples include a group, an oxetanyl group, a blocked isocyanate group and the like.
  • the blocked isocyanate group in the present disclosure is a group capable of generating an isocyanate group by heat, and for example, a group in which a blocking agent and an isocyanate group are reacted to protect the isocyanate group can be preferably exemplified.
  • the blocking agent examples include oxime compounds, lactam compounds, phenol compounds, alcohol compounds, amine compounds, active methylene compounds, pyrazole compounds, mercaptan compounds, imidazole compounds, and imide compounds.
  • the blocking agent examples include the compounds described in paragraphs 0115 to 0117 of JP-A-2017-07930, the contents of which are incorporated herein by reference.
  • the blocked isocyanate group is preferably a group capable of generating an isocyanate group by heat of 90 ° C. to 260 ° C.
  • the polymer chain represented by P 10 has at least one group (hereinafter, also referred to as “functional group A”) selected from the group consisting of a (meth) acryloyl group, an oxetanyl group, a blocked isocyanate group and a t-butyl group. Is preferable. More preferably, the functional group A is at least one selected from the group consisting of a (meth) acryloyl group, an oxetanyl group and a blocked isocyanate group. When the polymer chain contains a functional group A, it is easy to form a film having excellent solvent resistance.
  • the above effect is remarkable when it contains at least one group selected from a (meth) acryloyl group, an oxetanyl group and a blocked isocyanate group.
  • the functional group A has a t-butyl group, it is preferable that the composition contains a compound having an epoxy group or an oxetanyl group.
  • the functional group A has a blocked isocyanate group, it is preferable to include a compound having a hydroxy group in the composition.
  • the polymer chain represented by P 10 is more preferably a polymer chain having a repeating unit containing the functional group A in the side chain.
  • the proportion of the repeating unit containing the functional group A in the side chain in all the repeating units constituting P 10 is preferably 5% by mass or more, more preferably 10% by mass or more, and 20 It is more preferably mass% or more.
  • the upper limit can be 100% by mass, preferably 90% by mass or less, and more preferably 60% by mass or less.
  • the polymer chain represented by P 10 has a repeating unit containing an acid group.
  • the acid group include a carboxy group, a phosphoric acid group, a sulfo group, and a phenolic hydroxy group.
  • the dispersibility of the pigment in the composition can be further improved.
  • the developability can be further improved.
  • the proportion of the repeating unit containing an acid group is preferably 1% by mass to 30% by mass, more preferably 2% by mass to 20% by mass, and further preferably 3% by mass to 10% by mass. ..
  • Resin B can be produced by reacting at least one acid anhydride selected from the group consisting of aromatic tetracarboxylic acid anhydrides and aromatic tricarboxylic acid anhydrides with a hydroxy group-containing compound.
  • aromatic tetracarboxylic acid anhydride and the aromatic tricarboxylic acid anhydride include those described above.
  • the hydroxy group-containing compound is not particularly limited as long as it has a hydroxy group in the molecule, but is preferably a polyol having two or more hydroxy groups in the molecule. Further, as the hydroxy group-containing compound, it is also preferable to use a compound having two hydroxy groups and one thiol group in the molecule.
  • Examples of compounds having two hydroxy groups and one thiol group in the molecule include 1-mercapto-1,1-methanediol, 1-mercapto-1,1-ethanediol, and 3-mercapto-1,2-.
  • Examples of other hydroxy group-containing compounds include the compounds described in paragraphs 0084 to 0995 of JP-A-2018-101039, the contents of which are incorporated in the present specification.
  • the molar ratio of the acid anhydride group in the acid anhydride to the hydroxy group in the hydroxy group-containing compound is preferably 0.5 to 1.5.
  • the resin containing the repeating unit represented by the above formula (b-10) can be synthesized by the methods shown in the following synthesis methods (1) and (2).
  • a polymerizable monomer having an ethylenically unsaturated group is radically polymerized in the presence of a hydroxy group-containing thiol compound (preferably a compound having two hydroxy groups and one thiol group in the molecule) to form 2 in one terminal region.
  • a vinyl polymer having one hydroxy group is synthesized, and the synthesized vinyl polymer and one or more aromatic acid anhydrides selected from the group consisting of aromatic tetracarboxylic acid anhydrides and aromatic tricarboxylic acid anhydrides are obtained.
  • a method of reacting and producing is radically polymerized in the presence of a hydroxy group-containing thiol compound (preferably a compound having two hydroxy groups and one thiol group in the molecule) to form 2 in one terminal region.
  • a vinyl polymer having one hydroxy group is synthesized, and the synthesized vinyl polymer and one or more aromatic acid anhydrides selected from the group consisting of aromatic tetracarboxylic acid anhydrides
  • a polymerizable monomer having a hydroxy group may be radically polymerized, and then a compound having an isocyanate group (for example, a compound having an isocyanate group and the above-mentioned functional group A) may be reacted. .. This makes it possible to introduce functional group A into the polymer chain P 10.
  • a compound having an isocyanate group for example, a compound having an isocyanate group and the above-mentioned functional group A
  • the resin B can also be synthesized according to the method described in paragraphs 0120 to 0138 of JP2018-101039A.
  • the weight average molecular weight of the resin B is preferably 2,000 to 35,000.
  • the upper limit is more preferably 25,000 or less, further preferably 20,000 or less, and particularly preferably 15,000 or less.
  • the lower limit is more preferably 4,000 or more, further preferably 6,000 or more, and particularly preferably 7,000 or more.
  • Dispersants are also available as commercial products, and specific examples thereof include DISPERBYK series manufactured by BYK Chemie (for example, DISPERBYK-111, 161 etc.) and sparse sparse series manufactured by Nippon Lubrizol Co., Ltd. (for example, DISPERBYK-111, 161 etc.). For example, Solsparse 76500) and the like. Further, the pigment dispersant described in paragraphs 0041 to 0130 of JP2014-130338A can also be used, and the contents thereof are incorporated in the present specification. The resin described as the dispersant can also be used for purposes other than the dispersant. For example, it can also be used as a binder.
  • the total amount thereof is preferably in the following range.
  • the content of the resin is preferably 5% by mass to 40% by mass, based on the total solid content of the colored photosensitive composition, from the viewpoints of developing residue inhibitory property, dispersion stability, and adhesion. It is more preferably 10% by mass to 30% by mass, and particularly preferably 10% by mass to 25% by mass.
  • the colored photosensitive composition according to the present disclosure may contain a pigment derivative.
  • the pigment derivative include compounds having a structure in which a part of the chromophore is replaced with an acid group or a basic group.
  • the chromogens constituting the pigment derivative include quinoline skeleton, benzoimidazolone skeleton, diketopyrrolopyrrole skeleton, azo skeleton, phthalocyanine skeleton, anthracinone skeleton, quinacridone skeleton, dioxazine skeleton, perinone skeleton, perylene skeleton, thioindigo skeleton, and iso.
  • the azo skeleton and the benzoimidazolone skeleton are more preferable.
  • the acid group include a sulfo group, a carboxy group, a phosphoric acid group and salts thereof.
  • the atoms or groups of atoms that make up the salt include alkali metal ions (Li + , Na + , K +, etc.), alkaline earth metal ions (Ca 2+ , Mg 2+, etc.), ammonium ions, imidazolium ions, and pyridiniums.
  • Ions, phosphonium ions and the like can be mentioned.
  • the basic group include an amino group, a pyridinyl group and a salt thereof, a salt of an ammonium group, and a phthalimide methyl group.
  • the atom or atomic group constituting the salt include hydroxide ion, halogen ion, carboxylic acid ion, sulfonic acid ion, and phenoxide ion.
  • a pigment derivative having excellent visible transparency (hereinafter, also referred to as a transparent pigment derivative) can be used.
  • the maximum molar extinction coefficient ( ⁇ max) of the transparent pigment derivative in the wavelength region of 400 nm to 700 nm is preferably 3,000 L ⁇ mol -1 ⁇ cm -1 or less, and 1,000 L ⁇ mol -1 ⁇ cm -1. It is more preferably 100 L ⁇ mol -1 ⁇ cm -1 or less, and further preferably 100 L ⁇ mol -1 ⁇ cm -1 or less.
  • the lower limit of ⁇ max is, for example, 1 L ⁇ mol -1 ⁇ cm -1 or more, and may be 10 L ⁇ mol -1 ⁇ cm -1 or more.
  • pigment derivative examples include Japanese Patent Application Laid-Open No. 56-118462, Japanese Patent Application Laid-Open No. 63-264674, Japanese Patent Application Laid-Open No. 01-2170777, Japanese Patent Application Laid-Open No. 03-009961, and Japanese Patent Application Laid-Open No. 03-026767.
  • JP-A-10-195326 International Publication No. 2011/024896, Paragraphs 0083-0998, International Publication No. 2012/102399, Paragraphs 0063-0094, International Publication No. 2017/038252, Paragraph 0083 , Paragraph 0171 of JP-A-2015-151530, Paragraphs 0162 to 0183 of JP-A-2011-52065, JP-A-2003-081972, JP-A-5299151, JP-A-2015-172732, JP-A-2014. Examples thereof include the compounds described in JP-A-199308, JP-A-2014-0855562, JP-A-2014-035351, JP-A-2008-081565, and JP-A-2019-109512.
  • the colored photosensitive composition according to the present disclosure may contain one pigment derivative alone or two or more pigment derivatives.
  • the content of the pigment derivative is preferably 1 part by mass to 30 parts by mass, and more preferably 3 parts by mass to 20 parts by mass with respect to 100 parts by mass of the pigment. Only one type of pigment derivative may be used, or two or more types may be used in combination.
  • the colored photosensitive composition according to the present disclosure contains a photopolymerization initiator.
  • the colored photosensitive composition according to the present disclosure contains a polymerizable compound, it is preferable that the colored photosensitive composition according to the present disclosure further contains a photopolymerization initiator.
  • the photopolymerization initiator is not particularly limited and may be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light rays in the ultraviolet region to the visible light region is preferable.
  • the photopolymerization initiator is preferably a photoradical polymerization initiator.
  • photopolymerization initiator examples include halogenated hydrocarbon derivatives (for example, compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazoles, oxime compounds, organic peroxides, and thio compounds. , Ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds and the like.
  • the photopolymerization initiator is a trihalomethyltriazine compound, a benzyl dimethyl ketal compound, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, an acylphosphine compound, a phosphine oxide compound, a metallocene compound, an oxime compound, or a triarylimidazole.
  • a compound selected from the group consisting of a compound, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, and an acylphosphine compound is more preferable, and an oxime compound, that is, an oxime-based photopolymerization initiator is further preferable.
  • photopolymerization initiator the compounds described in paragraphs 0065 to 0111 of JP-A-2014-130173 and JP-A-6301489, MATERIAL STAGE 37-60p, vol. 19, No. 3.
  • ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (all manufactured by IGM Resins BV), Irgacure 184, Irgacure 1173, Irgacare 1173, Irgacure29. (Manufactured by the company) and the like.
  • Commercially available ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (above, IGM Resins BV), Irgacare 907, Irgacare 369, Irgacure 369, Irgacure 369, Irgar (Made) and so on.
  • acylphosphine compounds examples include Omnirad 819, Omnirad TPO (above, manufactured by IGM Resins BV), Irgacure 819, and Irgacure TPO (above, manufactured by BASF).
  • Examples of the oxime compound include the compounds described in JP-A-2001-233842, the compounds described in JP-A-2000-080068, and the compounds described in JP-A-2006-342166.
  • oxime compound examples include 3-benzoyloxyiminobutane-2-one, 3-acetoxyiminovtan-2-one, 3-propionyloxyiminovtan-2-one, 2-acetoxyimiminopentane-3-one, 2-acetoxyimino-1-phenylpropane-1-one, 2-benzoyloxyimino-1-phenylpropane-1-one, 3- (4-toluenesulfonyloxy) iminobutane-2-one, and 2-ethoxycarbonyloxy Examples thereof include imino-1-phenylpropane-1-one.
  • an oxime compound having a fluorene ring can also be used.
  • Specific examples of the oxime compound having a fluorene ring include the compounds described in JP-A-2014-137466.
  • an oxime compound having a skeleton in which at least one benzene ring of the carbazole ring is a naphthalene ring can also be used.
  • Specific examples of such an oxime compound include the compounds described in International Publication No. 2013/083505.
  • an oxime compound having a fluorine atom can also be used as the photopolymerization initiator.
  • Specific examples of the oxime compound having a fluorine atom are described in the compounds described in JP-A-2010-262028, compounds 24, 36-40 described in JP-A-2014-500852, and JP-A-2013-164471. Compound (C-3) and the like.
  • an oxime compound having a nitro group can be used as the photopolymerization initiator.
  • the oxime compound having a nitro group is also preferably a dimer.
  • Specific examples of the oxime compound having a nitro group include the compounds described in paragraphs 0031 to 0047 of JP2013-114249A, paragraphs 0008 to 0012 and 0070 to 0079 of JP2014-137466, and Patent No. Examples thereof include the compounds described in paragraphs 0007 to 0025 of Japanese Patent Application Laid-Open No. 4223071, ADEKA ARKULS NCI-831 (manufactured by ADEKA Corporation).
  • an oxime compound having a benzofuran skeleton can also be used.
  • Specific examples include OE-01 to OE-75 described in International Publication No. 2015/036910.
  • an oxime compound in which a substituent having a hydroxy group is bonded to the carbazole skeleton can also be used.
  • Examples of such a photopolymerization initiator include the compounds described in International Publication No. 2019/088055.
  • the oxime compound is preferably a compound having a maximum absorption wavelength in the wavelength range of 350 nm to 500 nm, and more preferably a compound having a maximum absorption wavelength in the wavelength range of 360 nm to 480 nm.
  • the molar extinction coefficient of the oxime compound at a wavelength of 365 nm or a wavelength of 405 nm is preferably high, more preferably 1,000 to 300,000, and more preferably 2,000 to 300,000 from the viewpoint of sensitivity. Is more preferable, and 5,000 to 200,000 is particularly preferable.
  • the molar extinction coefficient of a compound can be measured using a known method. For example, it is preferable to measure at a concentration of 0.01 g / L using ethyl acetate with a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian).
  • a bifunctional or trifunctional or higher functional photoradical polymerization initiator may be used as the photopolymerization initiator.
  • two or more radicals are generated from one molecule of the photoradical polymerization initiator, so that good sensitivity can be obtained.
  • the crystallinity is lowered, the solubility in a solvent or the like is improved, the precipitation is less likely to occur with time, and the stability of the colored photosensitive composition with time is improved. Can be done.
  • bifunctional or trifunctional or higher functional photo-radical polymerization initiators include JP-A-2010-527339, JP-A-2011-524436, International Publication No. 2015/004565, and JP-A-2016-532675.
  • Cmpd1-7 described in International Publication No. 2016/034963
  • Oxime Esters Photoinitiator described in paragraph 0007 of JP-A-2017-523465, Paragraph 0020- of JP2017-167399A.
  • the content of the photopolymerization initiator in the total solid content of the colored photosensitive composition is preferably 0.1% by mass to 30% by mass. ..
  • the lower limit is more preferably 0.5% by mass or more, and particularly preferably 1% by mass or more.
  • the upper limit is more preferably 20% by mass or less, and particularly preferably 15% by mass or less.
  • only one type of photopolymerization initiator may be used, or two or more types may be used. When two or more kinds are used, it is preferable that the total amount thereof is within the above range.
  • the colored photosensitive composition according to the present disclosure preferably contains a polymerizable compound.
  • a polymerizable compound a known compound that can be crosslinked by radicals, acids or heat can be used.
  • the polymerizable compound is preferably, for example, a compound having an ethylenically unsaturated group. Examples of the ethylenically unsaturated group include a vinyl group, a (meth) allyl group, and a (meth) acryloyl group.
  • the polymerizable compound used in the present disclosure is preferably a radically polymerizable compound.
  • the polymerizable compound may be in any chemical form such as a monomer, a prepolymer, or an oligomer, but a monomer is preferable.
  • the molecular weight of the polymerizable compound is preferably 100 to 3,000.
  • the upper limit is more preferably 2,000 or less, and even more preferably 1,500 or less.
  • the lower limit is more preferably 150 or more, and even more preferably 250 or more.
  • the polymerizable compound is preferably a compound containing 3 or more ethylenically unsaturated groups, more preferably a compound containing 3 to 15 ethylenically unsaturated groups, and 3 ethylenically unsaturated groups. It is more preferable that the compound contains up to 6 compounds.
  • the polymerizable compound is preferably a trifunctional to 15-functional (meth) acrylate compound, and more preferably a trifunctional to 6-functional (meth) acrylate compound.
  • polymerizable compound examples include paragraphs 0905 to 0108 of JP2009-288705A, paragraphs 0227 of JP2013-209760A, paragraphs 0254 to 0257 of JP2008-292970, and Japanese Patent Application Laid-Open No. 2013-.
  • examples thereof include the compounds described in paragraphs 0034 to 0038 of Japanese Patent Application Laid-Open No. 253224, paragraphs 0477 of Japanese Patent Application Laid-Open No. 2012-208494, Japanese Patent Application Laid-Open No. 2017-048367, Japanese Patent No. 6057891, and Japanese Patent No. 6031807. The contents of are incorporated herein by reference.
  • dipentaerythritol triacrylate (commercially available KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetraacrylate (commercially available KAYARAD D-320; Nihon Kayaku Co., Ltd.) ), Dipentaerythritol penta (meth) acrylate (commercially available KAYARAD D-310; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa (meth) acrylate (commercially available KAYARAD DPHA; Nippon Kayaku) NK ester A-DPH-12E manufactured by Shin-Nakamura Chemical Industry Co., Ltd., and a structure in which these (meth) acryloyl groups are bonded via ethylene glycol and / or propylene glycol residues.
  • Examples of the polymerizable compound include trimethylolpropane tri (meth) acrylate, trimethylolpropane propyleneoxy-modified tri (meth) acrylate, trimethylolpropane ethyleneoxy-modified tri (meth) acrylate, and isocyanurate ethyleneoxy-modified tri (meth) acrylate. It is also preferable to use a trifunctional (meth) acrylate compound such as pentaerythritol trimethylolpropane (meth) acrylate. Commercially available trifunctional (meth) acrylate compounds include Aronix M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306, and M-305.
  • M-303, M-452, M-450 manufactured by Toagosei Co., Ltd.
  • a polymerizable compound having an acid group can also be used.
  • the polymerizable compound having an acid group By using a polymerizable compound having an acid group, the colored photosensitive composition in the unexposed portion can be easily removed during development, and the generation of development residue can be suppressed.
  • the acid group include a carboxy group, a sulfo group, a phosphoric acid group and the like, and a carboxy group is preferable.
  • Examples of commercially available products of the polymerizable compound having an acid group include Aronix M-510, M-520, and Aronix TO-2349 (manufactured by Toagosei Co., Ltd.).
  • the preferable acid value of the polymerizable compound having an acid group is 0.1 mgKOH / g to 40 mgKOH / g, and more preferably 5 mgKOH / g to 30 mgKOH / g.
  • the acid value of the polymerizable compound is 0.1 mgKOH / g or more, the solubility in a developing solution is good, and when it is 40 mgKOH / g or less, it is advantageous in production and handling.
  • a polymerizable compound having a caprolactone structure can also be used.
  • Polymerizable compounds having a caprolactone structure are commercially available from Nippon Kayaku Co., Ltd. as the KAYARAD DPCA series, and examples thereof include DPCA-20, DPCA-30, DPCA-60, and DPCA-120.
  • a polymerizable compound having an alkyleneoxy group can also be used.
  • a polymerizable compound having an ethyleneoxy group and / or a propyleneoxy group is preferable, a polymerizable compound having an ethyleneoxy group is more preferable, and 3 to 3 having 4 to 20 ethyleneoxy groups.
  • a hexafunctional (meth) acrylate compound is more preferred.
  • Commercially available products of the polymerizable compound having an alkyleneoxy group include SR-494, which is a tetrafunctional (meth) acrylate having four ethyleneoxy groups manufactured by Sartomer, and a trifunctional (meth) having three isobutyleneoxy groups. Examples thereof include KAYARAD TPA-330, which is an acrylate.
  • a polymerizable compound having a fluorene skeleton can also be used.
  • examples of commercially available products of the polymerizable compound having a fluorene skeleton include Ogsol EA-0200 and EA-0300 (manufactured by Osaka Gas Chemical Co., Ltd., a (meth) acrylate monomer having a fluorene skeleton).
  • the polymerizable compound it is also preferable to use a compound that does not substantially contain an environmentally regulated substance such as toluene.
  • an environmentally regulated substance such as toluene.
  • commercially available products of such compounds include KAYARAD DPHA LT and KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.).
  • Examples of the polymerizable compound include urethane acrylates described in Japanese Patent Application Laid-Open No. 48-041708, Japanese Patent Application Laid-Open No. 51-0371993, Japanese Patent Application Laid-Open No. 02-032293, and Japanese Patent Application Laid-Open No. 02-016765, and Japanese Patent Application Laid-Open No. 58- Urethane compounds having an ethylene oxide-based skeleton described in Japanese Patent Publication No. 049860, Japanese Patent Publication No. 56-017654, Japanese Patent Publication No. 62-039417, Japanese Patent Publication No. 62-039418, Japanese Patent Application Laid-Open No. 63-277653, Japanese Patent Application Laid-Open No.
  • a polymerizable compound having an amino structure or a sulfide structure in the molecule described in JP-A-63-260909 and JP-A-01-105238.
  • the polymerizable compounds include UA-7200 (manufactured by Shin-Nakamura Chemical Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, and AH-600. , T-600, AI-600, LINK-202UA (manufactured by Kyoeisha Chemical Co., Ltd.) and the like can also be used.
  • the content of the polymerizable compound in the total solid content of the colored photosensitive composition may be 0.1% by mass to 50% by mass. preferable.
  • the lower limit is more preferably 0.5% by mass or more, and further preferably 1% by mass or more.
  • the upper limit is more preferably 45% by mass or less, further preferably 40% by mass or less.
  • the total content of the polymerizable compound and the resin in the total solid content of the colored photosensitive composition is preferably 10% by mass to 65% by mass from the viewpoint of curability, developability and film forming property.
  • the lower limit is more preferably 15% by mass or more, further preferably 20% by mass or more, and particularly preferably 30% by mass or more.
  • the upper limit is more preferably 60% by mass or less, further preferably 50% by mass or less, and particularly preferably 40% by mass or less. Further, it is preferable that the resin is contained in an amount of 30 parts by mass to 300 parts by mass with respect to 100 parts by mass of the polymerizable compound.
  • the lower limit is more preferably 50 parts by mass or more, and particularly preferably 80 parts by mass or more.
  • the upper limit is more preferably 250 parts by mass or less, and particularly preferably 200 parts by mass or less.
  • the colored photosensitive composition according to the present disclosure only one type of polymerizable compound may be used, or two or more types may be used. When two or more kinds are used, it is preferable that the total amount thereof is within the above range.
  • the colored photosensitive composition according to the present disclosure may contain a compound having a cyclic ether group.
  • the cyclic ether group include an epoxy group and an oxetanyl group.
  • the compound having a cyclic ether group is preferably a compound having an epoxy group.
  • the compound having an epoxy group include a compound having one or more epoxy groups in one molecule, and a compound having two or more epoxy groups is preferable. It is preferable to have 1 to 100 epoxy groups in one molecule.
  • the upper limit of the epoxy group may be, for example, 10 or less, or 5 or less.
  • the lower limit of the epoxy group is preferably two or more.
  • the compound having an epoxy group may be a low molecular weight compound (for example, a molecular weight of less than 2,000, further, a molecular weight of less than 1,000), or a polymer compound (for example, a polymer having a molecular weight of 1,000 or more and a polymer).
  • a weight average molecular weight of 1,000 or more has a weight average molecular weight of 1,000 or more).
  • the weight average molecular weight of the compound having an epoxy group is preferably 200 to 100,000, more preferably 500 to 50,000.
  • the upper limit of the weight average molecular weight is more preferably 10,000 or less, particularly preferably 5,000 or less, and most preferably 3,000 or less.
  • an epoxy resin can be preferably used as the compound having an epoxy group.
  • the epoxy resin include an epoxy resin which is a glycidyl etherified product of a phenol compound, an epoxy resin which is a glycidyl etherified product of various novolak resins, an alicyclic epoxy resin, an aliphatic epoxy resin, a heterocyclic epoxy resin, and a glycidyl ester type.
  • the epoxy equivalent of the epoxy resin is preferably 310 g / eq to 3,300 g / eq, more preferably 310 g / eq to 1,700 g / eq, and more preferably 310 g / eq to 1,000 g / eq. Is more preferable.
  • EHPE3150 manufactured by Daicel Corporation
  • EPICLON N-695 manufactured by DIC Corporation
  • Marproof G-0150M G-0105SA, G-0130SP, G. -0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, G-01758 (all manufactured by NOF CORPORATION, epoxy group-containing polymer) and the like can be mentioned.
  • the content of the compound having a cyclic ether group in the total solid content of the colored photosensitive composition is 0.1% by mass to 20% by mass. It is preferably mass%.
  • the lower limit is more preferably 0.5% by mass or more, and particularly preferably 1% by mass or more.
  • the upper limit is more preferably 15% by mass or less, and particularly preferably 10% by mass or less.
  • only one compound having a cyclic ether group may be used, or two or more compounds may be used. When two or more kinds are used, it is preferable that the total amount thereof is within the above range.
  • the colored photosensitive composition according to the present disclosure may contain a silane coupling agent.
  • the adhesion of the obtained film to the support can be further improved.
  • the silane coupling agent means a silane compound having a hydrolyzable group and other functional groups.
  • the hydrolyzable group refers to a substituent that is directly linked to a silicon atom and can form a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction. Examples of the hydrolyzable group include a halogen atom, an alkoxy group, an acyloxy group and the like, and an alkoxy group is preferable.
  • the silane coupling agent is preferably a compound having an alkoxysilyl group.
  • the functional group other than the hydrolyzable group include a vinyl group, a (meth) allyl group, a (meth) acryloyl group, a mercapto group, an epoxy group, an oxetanyl group, an amino group, a ureido group, a sulfide group and an isocyanate group.
  • a phenyl group and the like preferably an amino group, a (meth) acryloyl group and an epoxy group.
  • silane coupling agent examples include N- ⁇ -aminoethyl- ⁇ -aminopropylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-602), N- ⁇ -aminoethyl- ⁇ -amino.
  • Propyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-603), N- ⁇ -minoethyl- ⁇ -aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBE-602), ⁇ -Aminopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-903), ⁇ -aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBE-903), 3-methacryloxypropyl Methyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-502), 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical
  • silane coupling agent examples include the compounds described in paragraphs 0018 to 0036 of JP2009-288703A and the compounds described in paragraphs 0056 to 0066 of JP2009-242604A. The contents of are incorporated herein by reference.
  • the content of the silane coupling agent in the total solid content of the colored photosensitive composition is preferably 0.1% by mass to 5% by mass. ..
  • the upper limit is more preferably 3% by mass or less, and particularly preferably 2% by mass or less.
  • the lower limit is more preferably 0.5% by mass or more, and particularly preferably 1% by mass or more.
  • only one type of silane coupling agent may be used, or two or more types may be used. When two or more kinds are used, it is preferable that the total amount thereof is within the above range.
  • the colored photosensitive composition according to the present disclosure preferably contains an organic solvent.
  • the organic solvent include ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, hydrocarbon solvents and the like.
  • paragraph 0223 of WO 2015/166779 can be referred to, the contents of which are incorporated herein by reference.
  • an ester solvent substituted with a cyclic alkyl group and a ketone solvent substituted with a cyclic alkyl group can also be preferably used.
  • organic solvent examples include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2 -Heptanone, cyclohexanone, cyclohexyl acetate, cyclopentanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N, N-dimethylpropanamide, 3-butoxy-N , N-Dimethylpropanamide and the like.
  • aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may need to be reduced for environmental reasons (for example, 50 mass ppm (parts) with respect to the total amount of organic solvent. Per million) or less, 10 mass ppm or less, or 1 mass ppm or less).
  • an organic solvent having a low metal content it is preferable to use an organic solvent having a low metal content, and the metal content of the organic solvent is preferably, for example, 10 mass ppb (parts per parts) or less. If necessary, an organic solvent at the mass ppt (parts per trillion) level may be used, and such an organic solvent is provided by, for example, Toyo Synthetic Co., Ltd. (The Chemical Daily, November 13, 2015).
  • Examples of the method for removing impurities such as metals from the organic solvent include distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter.
  • the filter pore diameter of the filter used for filtration is preferably 10 ⁇ m or less, more preferably 5 ⁇ m or less, and even more preferably 3 ⁇ m or less.
  • the filter material is preferably polytetrafluoroethylene, polyethylene or nylon.
  • the organic solvent may contain isomers (compounds having the same number of atoms but different structures). Further, only one kind of isomer may be contained, or a plurality of kinds may be contained.
  • the content of peroxide in the organic solvent is preferably 0.8 mmol / L or less, and more preferably substantially free of peroxide.
  • the content of the organic solvent in the colored photosensitive composition is preferably 10% by mass to 95% by mass, more preferably 20% by mass to 90% by mass, and 30% by mass to 90% by mass. Is even more preferable.
  • the colored photosensitive composition according to the present disclosure does not substantially contain an environmentally regulated substance from the viewpoint of environmentally regulated.
  • the fact that the environmentally regulated substance is substantially not contained means that the content of the environmentally regulated substance in the colored photosensitive composition is 50 mass ppm or less, and is 30 mass ppm or less. Is preferable, and it is more preferably 10 mass ppm or less, and particularly preferably 1 mass ppm or less.
  • environmentally regulated substances include benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene.
  • REACH Registration Evolution Analysis and Restriction of Chemicals
  • PRTR Policy Release and Transfer Register
  • VOC Volatile Organic Compounds
  • VOC Volatile Organic Compounds
  • VOC Volatile Organic Compounds
  • VOC Volatile Organic Compounds
  • VOC Volatile Organic Compounds
  • VOC Volatile Organic Compounds
  • VOC Volatile Organic Compounds
  • VOC Volatile Organic Compounds
  • VOC Volatile Organic Compounds
  • Examples of the method for reducing the environmentally regulated substance include a method of heating or depressurizing the inside of the system to raise the boiling point of the environmentally regulated substance to the boiling point or higher, and distilling off the environmentally regulated substance from the system to reduce the amount of the environmentally regulated substance. Further, when distilling off a small amount of an environmentally regulated substance, it is also useful to azeotrope with a solvent having a boiling point equivalent to that of the solvent in order to improve efficiency.
  • a polymerization inhibitor or the like is added and distilled under reduced pressure in order to prevent the radical polymerization reaction from proceeding and cross-linking between molecules during distillation under reduced pressure. You may.
  • distillation methods are performed at the stage of the raw material, the stage of the product obtained by reacting the raw materials (for example, a resin solution after polymerization or a polyfunctional monomer solution), or a colored photosensitive composition prepared by mixing these compounds. It is possible at any stage such as a stage.
  • perfluoroalkyl sulfonic acid and its salt and perfluoroalkyl carboxylic acid and its salt may be regulated.
  • the photosensitive composition according to the present disclosure when the content of the above-mentioned compound is reduced, perfluoroalkyl sulfonic acid (particularly, perfluoroalkyl sulfonic acid having 6 to 8 carbon atoms in a perfluoroalkyl group) and a salt thereof,
  • the content of perfluoroalkylcarboxylic acid (particularly perfluoroalkylcarboxylic acid having 6 to 8 carbon atoms in the perfluoroalkyl group) and a salt thereof is 0.01 ppb or more with respect to the total solid content of the photosensitive composition.
  • the photosensitive composition according to the present disclosure may be substantially free of perfluoroalkyl sulfonic acid and salts thereof, and perfluoroalkyl carboxylic acid and salts thereof.
  • perfluoroalkyl sulfonic acid and its salt and a compound that can substitute for perfluoroalkyl carboxylic acid and its salt, perfluoroalkyl sulfonic acid and its salt, and perfluoroalkyl carboxylic acid can be used.
  • a photosensitive composition that is substantially free of salts thereof may be selected.
  • compounds that can substitute for the regulated compound include compounds excluded from the regulation due to the difference in the number of carbon atoms of the perfluoroalkyl group. However, the above contents do not prevent the use of perfluoroalkyl sulfonic acid and its salt, and perfluoroalkyl carboxylic acid and its salt.
  • the photosensitive composition according to the present disclosure may contain a perfluoroalkyl sulfonic acid and a salt thereof, and a perfluoroalkyl carboxylic acid and a salt thereof within the maximum allowable range.
  • the colored photosensitive composition according to the present disclosure may contain a polymerization inhibitor.
  • the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis (3-methyl-6-tert-butylphenol), and the like. Examples thereof include 2,2'-methylenebis (4-methyl-6-t-butylphenol) and N-nitrosophenylhydroxyamine salts (ammonium salt, primary cerium salt, etc.). Of these, p-methoxyphenol is preferable.
  • the content of the polymerization inhibitor in the total solid content of the colored photosensitive composition is preferably 0.0001% by mass to 5% by mass.
  • the colored photosensitive composition according to the present disclosure may contain a surfactant.
  • a surfactant various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone-based surfactant can be used.
  • the surfactant the surfactant described in paragraphs 0238 to 0245 of International Publication No. 2015/166779 is mentioned, and the content thereof is incorporated in the present specification.
  • the surfactant is preferably a fluorine-based surfactant.
  • the liquid characteristics particularly, fluidity
  • the liquid saving property can be further improved. It is also possible to form a film having a small thickness unevenness.
  • the fluorine content in the fluorine-based surfactant is preferably 3% by mass to 40% by mass, more preferably 5% by mass to 30% by mass, and particularly preferably 7% by mass to 25% by mass.
  • a fluorine-based surfactant having a fluorine content within this range is effective in terms of uniformity of coating film thickness and liquid saving property, and has good solubility in a colored photosensitive composition.
  • fluorine-based surfactant examples include the surfactants described in paragraphs 0060 to 0064 of Japanese Patent Application Laid-Open No. 2014-041318 (paragraphs 0060 to 0064 of the corresponding International Publication No. 2014/017669) and the like, Japanese Patent Application Laid-Open No. 2011-132503.
  • the surfactants described in paragraphs 0117 to 0132 of the publication are mentioned and their contents are incorporated herein by reference.
  • fluorine-based surfactants include, for example, Megafuck F171, F172, F173, F176, F177, F141, F142, F143, F144, R30, F437, F475, F479, F482, F554, F780, EXP, MFS.
  • the fluorine-based surfactant has a molecular structure having a functional group containing a fluorine atom, and an acrylic compound in which a portion of the functional group containing a fluorine atom is cut off and the fluorine atom volatilizes when heat is applied.
  • fluorine-based surfactants include the Megafuck DS series manufactured by DIC Corporation (The Chemical Daily (February 22, 2016), Nikkei Sangyo Shimbun (February 23, 2016)), for example, Megafuck. DS-21 can be mentioned.
  • the fluorine-based surfactant it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound.
  • a fluorine-based surfactant the description in JP-A-2016-216602 can be referred to, and the content thereof is incorporated in the present specification.
  • a block polymer can also be used as the fluorine-based surfactant.
  • the fluorine-based surfactant has a repeating unit derived from a (meth) acrylate compound having a fluorine atom and 2 or more (preferably 5 or more) alkyleneoxy groups (preferably ethyleneoxy groups and propyleneoxy groups) (meth).
  • a fluorine-containing polymer compound containing a repeating unit derived from an acrylate compound can also be preferably used.
  • the fluorine-containing surfactants described in paragraphs 0016 to 0037 of JP-A-2010-032698 and the following compounds are also exemplified as the fluorine-based surfactants used in the present disclosure.
  • the weight average molecular weight of the above compound is preferably 3,000 to 50,000, for example, 14,000.
  • % indicating the ratio of the repeating unit is mol%.
  • a fluorine-based surfactant a fluorine-containing polymer having an ethylenically unsaturated group in the side chain can also be used.
  • Specific examples include the compounds described in paragraphs 0050 to 0090 and paragraphs 0289 to 0295 of JP2010-164965, for example, Megafuck RS-101, RS-102, RS-718K, RS manufactured by DIC Corporation. -72-K and the like can be mentioned.
  • the fluorine-based surfactant the compounds described in paragraphs 0015 to 0158 of JP2015-117327A can also be used.
  • Nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane and their ethoxylates and propoxylates (eg, glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, etc.
  • silicone-based surfactant examples include Torre Silicone DC3PA, Torre Silicone SH7PA, Torre Silicone DC11PA, Torre Silicone SH21PA, Torre Silicone SH28PA, Torre Silicone SH29PA, Torre Silicone SH30PA, Torre Silicone SH8400 (all, Toray Dow Corning Co., Ltd.). ), TSF-4440, TSF-4300, TSF-4445, TSF-4460, TSF-4452 (above, manufactured by Momentive Performance Materials), KP-341, KF-6001, KF-6002 (above, (Shinetsu Silicone Co., Ltd.), BYK307, BYK323, BYK330 (all manufactured by Big Chemie) and the like.
  • the content of the surfactant in the total solid content of the colored photosensitive composition is preferably 0.001% by mass to 5.0% by mass, more preferably 0.005% by mass to 3.0% by mass.
  • the colored photosensitive composition according to the present disclosure only one type of surfactant may be used, or two or more types may be used. When two or more kinds are used, it is preferable that the total amount thereof is within the above range.
  • the colored photosensitive composition according to the present disclosure may contain an ultraviolet absorber.
  • an ultraviolet absorber a conjugated diene compound, an aminodiene compound, a salicylate compound, a benzophenone compound, a benzotriazole compound, an acrylonitrile compound, a hydroxyphenyltriazine compound, an indol compound, a triazine compound and the like can be used.
  • the compounds described in paragraphs 0052 to 0072 of JP2012-208374A, paragraphs 0317 to 0334 of JP2013-068814, and paragraphs 0061 to 0080 of JP2016-162946 can be used. These contents are incorporated herein by reference.
  • Examples of commercially available ultraviolet absorbers include UV-503 (manufactured by Daito Kagaku Co., Ltd.).
  • Examples of the benzotriazole compound include the MYUA series manufactured by Miyoshi Oil & Fat Co., Ltd. (The Chemical Daily, February 1, 2016).
  • the ultraviolet absorber the compounds described in paragraphs 0049 to 0059 of Japanese Patent No. 6268967 can also be used.
  • the content of the ultraviolet absorber in the total solid content of the colored photosensitive composition is preferably 0.01% by mass to 10% by mass, more preferably 0.01% by mass to 5% by mass.
  • only one type of ultraviolet absorber may be used, or two or more types may be used. When two or more kinds are used, it is preferable that the total amount thereof is within the above range.
  • the colored photosensitive composition according to the present disclosure may contain an antioxidant.
  • the antioxidant include a phenol compound, a phosphite ester compound, a thioether compound and the like.
  • the phenol compound any phenol compound known as a phenolic antioxidant can be used.
  • Preferred phenolic compounds include hindered phenolic compounds.
  • a compound having a substituent at a site (ortho position) adjacent to the phenolic hydroxy group is preferable.
  • a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferable.
  • a compound having a phenol group and a phosphite ester group in the same molecule is also preferable.
  • a phosphorus-based antioxidant can also be preferably used.
  • a phosphorus-based antioxidant tris [2-[[2,4,8,10-tetrakis (1,1-dimethylethyl) dibenzo [d, f] [1,3,2] dioxaphosfepine-6 -Il] Oxy] Ethyl] amine, Tris [2-[(4,6,9,11-tetra-tert-butyldibenzo [d, f] [1,3,2] dioxaphosfepin-2-yl] ) Oxy] ethyl] amine, ethylbis phosphite (2,4-di-tert-butyl-6-methylphenyl) and the like.
  • antioxidants include, for example, Adekastab AO-20, Adekastab AO-30, Adekastab AO-40, Adekastab AO-50, Adekastab AO-50F, Adekastab AO-60, Adekastab AO-60G, Adekastab AO-80. , ADEKA STAB AO-330 (above, manufactured by ADEKA Corporation) and the like. Further, as the antioxidant, the compounds described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, the compounds described in Japanese Patent No. 10-2019-0059371, and the like can also be used.
  • the content of the antioxidant in the total solid content of the colored photosensitive composition is preferably 0.01% by mass to 20% by mass, and more preferably 0.3% by mass to 15% by mass.
  • the colored photosensitive composition according to the present disclosure only one type of antioxidant may be used, or two or more types may be used. When two or more kinds are used, it is preferable that the total amount thereof is within the above range.
  • the colored photosensitive composition according to the present disclosure includes, if necessary, a sensitizer, a curing accelerator, a filler, a thermosetting accelerator, a plasticizer and other auxiliary agents (for example, conductive particles, a filler, an erasing agent). It may contain a foaming agent, a flame retardant, a leveling agent, a peeling accelerator, a fragrance, a surface tension adjusting agent, a chain transfer agent, etc.). By appropriately containing these components, properties such as film physical characteristics can be adjusted. These components are described in, for example, paragraphs 0183 and later of JP2012-003225A (paragraph 0237 of the corresponding US Patent Application Publication No.
  • the coloring composition according to the present disclosure may contain a latent antioxidant, if necessary.
  • the latent antioxidant is a compound in which the site that functions as an antioxidant is protected by a protecting group, and is heated at 100 ° C. to 250 ° C. or at 80 ° C. to 200 ° C. in the presence of an acid / base catalyst. Examples thereof include compounds in which the protecting group is eliminated by heating and the compound functions as an antioxidant. Examples of the latent antioxidant include compounds described in International Publication No. 2014/021023, International Publication No.
  • Examples of commercially available products of latent antioxidants include ADEKA ARKULS GPA-5001 (manufactured by ADEKA Corporation) and the like. Further, as described in Japanese Patent Application Laid-Open No. 2018-155881, C.I. I. Pigment Yellow 129 may be added for the purpose of improving weather resistance.
  • the colored photosensitive composition according to the present disclosure may contain a metal oxide in order to adjust the refractive index of the obtained film.
  • the metal oxide include TiO 2 , ZrO 2 , Al 2 O 3 , SiO 2 and the like.
  • the primary particle size of the metal oxide is preferably 1 nm to 100 nm, more preferably 3 nm to 70 nm, and particularly preferably 5 nm to 50 nm.
  • the metal oxide may have a core-shell structure. Further, in this case, the core portion may be hollow.
  • the colored photosensitive composition according to the present disclosure may contain a light resistance improving agent.
  • the light resistance improving agent include the compounds described in paragraphs 0036 to 0037 of JP-A-2017-198787, the compounds described in paragraphs 0029 to 0034 of JP-A-2017-146350, and paragraphs of JP-A-2017-129774.
  • the colored photosensitive composition according to the present disclosure preferably has a free metal content of 100 ppm or less, more preferably 50 ppm or less, and 10 ppm or less, which is not bonded or coordinated with a pigment or the like. Is more preferable, and it is particularly preferable that the content is substantially not contained.
  • stabilization of pigment dispersibility agglomeration suppression
  • improvement of spectral characteristics due to improvement of dispersibility agglomeration suppression
  • stabilization of curable components suppression of conductivity fluctuation due to elution of metal atoms / metal ions
  • Effects such as improvement of characteristics can be expected.
  • the types of free metals include Na, K, Ca, Sc, Ti, Mn, Cu, Zn, Fe, Cr, Co, Mg, Al, Sn, Zr, Ga, Ge, Ag, Au, Pt, and the like.
  • the content of free halogen not bonded or coordinated with a pigment or the like is preferably 100 ppm or less, more preferably 50 ppm or less, and 10 ppm or less. It is more preferable that it is present, and it is particularly preferable that it is not substantially contained.
  • the halogen include F, Cl, Br, I and their anions.
  • the method for reducing free metals and halogens in the colored photosensitive composition include methods such as washing with ion-exchanged water, filtration, ultrafiltration, and purification with an ion-exchange resin.
  • the colored photosensitive composition according to the present disclosure may contain a dye.
  • a dye a known dye can be used.
  • the dye include pyrazole azo compound, anilino azo compound, triarylmethane compound, anthraquinone compound, anthrapyridone compound, benzylidene compound, oxonor compound, pyrazorotriazole azo compound, pyridone azo compound, cyanine compound, phenothiazine compound and pyropyrazole azomethine compound.
  • the dye examples include the methine dye described in JP-A-2019-73695, the methine dye described in JP-A-2019-073696, the methine dye described in JP-A-2019-73697, and JP-A-2019. Examples thereof include the methine dyes described in Japanese Patent Application Laid-Open No. 73698.
  • a dye multimer can also be used in the colored photosensitive composition according to the present disclosure.
  • the dye multimer is preferably a dye that is used by dissolving it in a solvent. Further, the dye multimer may form particles. When the dye multimer is a particle, it is usually used in a state of being dispersed in a solvent.
  • the pigment multimer in the particle state can be obtained by, for example, emulsion polymerization, and specific examples thereof include the compounds and production methods described in JP-A-2015-214682.
  • the dye multimer has two or more dye structures in one molecule, and preferably has three or more dye structures.
  • the upper limit is not particularly limited, but may be 100 or less.
  • the plurality of dye structures contained in one molecule may have the same dye structure or different dye structures.
  • the weight average molecular weight (Mw) of the dye multimer is preferably 2,000 to 50,000.
  • the lower limit is more preferably 3,000 or more, and even more preferably 6,000 or more.
  • the upper limit is more preferably 30,000 or less, further preferably 20,000 or less.
  • Dye multimers are described in JP-A-2011-213925, JP-A-2013-041097, JP-A-2015-028144, JP-A-2015-030742, International Publication No. 2016/031442, and the like. Compounds can also be used.
  • the content of the dye is preferably less than the content of the pigment.
  • the colored photosensitive composition according to the present disclosure does not substantially contain a terephthalic acid ester.
  • the water content of the colored photosensitive composition according to the present disclosure is preferably 3% by mass or less, more preferably 0.01% by mass to 1.5% by mass, and 0.1% by mass to 1. It is particularly preferably 0% by mass.
  • the water content can be measured by the Karl Fischer method.
  • the colored photosensitive composition according to the present disclosure can be used by adjusting the viscosity for the purpose of adjusting the film surface (flatness, etc.), adjusting the film thickness, and the like.
  • the viscosity value can be appropriately selected as needed, but for example, at 23 ° C., 0.3 mPa ⁇ s to 50 mPa ⁇ s is preferable, and 0.5 mPa ⁇ s to 20 mPa ⁇ s is more preferable.
  • a viscometer RE85L rotor: 1 ° 34'x R24, measuring range 0.6 to 1,200 mPa ⁇ s
  • Toki Sangyo Co., Ltd. is used, and the temperature is adjusted to 23 ° C. Can be measured in the state where
  • the voltage retention rate of the liquid crystal display element provided with the color filter is preferably 70% or more, preferably 90% or more. Is more preferable.
  • Known means for obtaining a high voltage holding ratio can be appropriately incorporated, and typical means include the use of a high-purity material (for example, reduction of ionic impurities) and control of the amount of acid groups in the composition. Can be mentioned.
  • the voltage retention rate can be measured by, for example, the methods described in paragraphs 0243 of JP2011-008004A and paragraphs 0123 to 0129 of JP2012-224847A.
  • the container for the colored photosensitive composition according to the present disclosure is not particularly limited, and a known container can be used. Further, as a storage container, a multi-layer bottle having a container inner wall composed of 6 types and 6 layers of resin and 6 types of resin having a 7-layer structure for the purpose of suppressing impurities from being mixed into the raw material or the colored photosensitive composition. It is also preferable to use a bottle of plastic. Examples of such a container include the container described in Japanese Patent Application Laid-Open No. 2015-123351. Further, the inner wall of the colored photosensitive composition is preferably made of glass or stainless steel for the purpose of preventing metal elution from the inner wall of the container, improving the storage stability of the composition, and suppressing the alteration of components. ..
  • the storage conditions for the colored photosensitive composition according to the present disclosure are not particularly limited, and conventionally known methods can be used. Further, the method described in JP-A-2016-180058 can also be used.
  • the colored photosensitive composition according to the present disclosure can be prepared by mixing the above-mentioned components.
  • all the components may be simultaneously dissolved and / or dispersed in a solvent to prepare the colored photosensitive composition, or if necessary, two or more solutions of each component may be appropriately prepared.
  • a colored photosensitive composition may be prepared by preparing a dispersion liquid and mixing them at the time of use (at the time of application).
  • the mechanical force used for dispersing the pigment includes compression, squeezing, impact, shearing, cavitation and the like.
  • Specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high speed impellers, sand grinders, flow jet mixers, high pressure wet atomization, ultrasonic dispersion and the like.
  • the pulverization of the pigment in the sand mill (bead mill) it is preferable to use beads having a small diameter and to process under the condition that the pulverization efficiency is increased by increasing the filling rate of the beads. Further, it is preferable to remove coarse particles by filtration, centrifugation or the like after the pulverization treatment.
  • the process and disperser for dispersing pigments are "Dispersion Technology Taizen, published by Information Organization Co., Ltd., July 15, 2005" and "Dispersion technology and industrial application centered on suspension (solid / liquid dispersion system)".
  • the process and disperser described in paragraph 0022 of JP-A-2015-157893, "Comprehensive Data Collection, Published by Management Development Center Publishing Department, October 10, 1978" can be preferably used.
  • the particles may be miniaturized in the salt milling step.
  • the materials, equipment, processing conditions, etc. used in the salt milling step for example, the descriptions in JP-A-2015-194521 and JP-A-2012-046629 can be referred to.
  • any filter that has been conventionally used for filtration or the like can be used without particular limitation.
  • fluororesins such as polytetrafluoroethylene (PTFE), polyamide resins such as nylon (eg nylon-6, nylon-6,6), and polyolefin resins such as polyethylene and polypropylene (PP) (high density, ultrahigh molecular weight).
  • PTFE polytetrafluoroethylene
  • nylon eg nylon-6, nylon-6,6)
  • polyolefin resins such as polyethylene and polypropylene (PP) (high density, ultrahigh molecular weight
  • filters using materials such as (including polyolefin resin).
  • polypropylene (including high-density polypropylene) and nylon are preferable.
  • the pore size of the filter is preferably 0.01 ⁇ m to 7.0 ⁇ m, more preferably 0.01 ⁇ m to 3.0 ⁇ m, and even more preferably 0.05 ⁇ m to 0.5 ⁇ m. If the pore size of the filter is within the above range, fine foreign matter can be removed more reliably.
  • the nominal value of the filter manufacturer can be referred to.
  • various filters provided by Nippon Pole Co., Ltd. (DFA4201NIEY, etc.), Advantech Toyo Co., Ltd., Japan Entegris Co., Ltd. (formerly Nippon Microlith Co., Ltd.), KITZ Microfilter Co., Ltd., etc. can be used.
  • fibrous filter medium examples include polypropylene fiber, nylon fiber, glass fiber and the like.
  • examples of commercially available products include SBP type series (SBP008, etc.), TPR type series (TPR002, TPR005, etc.) and SHPX type series (SHPX003, etc.) manufactured by Roki Techno Co., Ltd.
  • filters for example, a first filter and a second filter
  • the filtration with each filter may be performed only once or twice or more.
  • filters having different pore diameters may be combined within the above-mentioned range.
  • the filtration with the first filter may be performed only on the dispersion liquid, and after mixing the other components, the filtration may be performed with the second filter.
  • the cured product according to the present disclosure is a cured product obtained by curing the colored photosensitive composition according to the present disclosure.
  • the cured product according to the present disclosure can be suitably used for a color filter or the like. Specifically, it can be preferably used as a colored layer (pixel) of a color filter, and more specifically, it can be preferably used as a red colored layer (red pixel) of a color filter.
  • the cured product according to the present disclosure is preferably a film-like cured product, and the film thickness thereof can be appropriately adjusted according to the intended purpose.
  • the film thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and even more preferably 5 ⁇ m or less.
  • the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and further preferably 0.3 ⁇ m or more.
  • the color filter according to the present disclosure includes the cured product according to the present disclosure described above. More preferably, it has a cured film according to the present disclosure as a pixel of a color filter.
  • the color filter according to the present disclosure can be used for a solid-state image sensor such as a CCD (charge-coupled device) or CMOS (complementary metal oxide semiconductor), an image display device, or the like.
  • the film thickness according to the present disclosure can be appropriately adjusted according to the purpose.
  • the film thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and even more preferably 5 ⁇ m or less.
  • the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and further preferably 0.3 ⁇ m or more.
  • the color filter according to the present disclosure preferably has a pixel width of 0.5 ⁇ m to 20.0 ⁇ m.
  • the lower limit is more preferably 1.0 ⁇ m or more, and particularly preferably 2.0 ⁇ m or more.
  • the upper limit is more preferably 15.0 ⁇ m or less, and particularly preferably 10.0 ⁇ m or less.
  • the Young's modulus of the pixel is preferably 0.5 GPa to 20 GPa, more preferably 2.5 GPa to 15 GPa.
  • each pixel included in the color filter according to the present disclosure has high flatness.
  • the surface roughness Ra of the pixel is preferably 100 nm or less, more preferably 40 nm or less, and further preferably 15 nm or less.
  • the lower limit is not specified, but it is preferably 0.1 nm or more, for example.
  • the surface roughness of the pixels can be measured using, for example, an AFM (atomic force microscope) Measurement 3100 manufactured by Veeco.
  • the contact angle of water on the pixel can be appropriately set to a preferable value, but is typically in the range of 50 ° to 110 °.
  • the contact angle can be measured using, for example, a contact angle meter CV-DT ⁇ A type (manufactured by Kyowa Interface Science Co., Ltd.). Further, it is preferable that the volume resistance value of the pixel is high. Specifically, it is preferred that the volume resistivity value of the pixel is 10 9 ⁇ ⁇ cm or more, and more preferably 10 11 ⁇ ⁇ cm or more. The upper limit is not specified, but it is preferably 10 14 ⁇ ⁇ cm or less, for example.
  • the volume resistance value of the pixel can be measured using, for example, an ultra-high resistance meter 5410 (manufactured by Advantest).
  • the color filter according to the present disclosure may be provided with a protective layer on the surface of the film according to the present disclosure.
  • a protective layer By providing the protective layer, various functions such as oxygen blocking, low reflection, hydrophobicization, and shielding of light of a specific wavelength (ultraviolet rays, near infrared rays, etc.) can be imparted.
  • the thickness of the protective layer is preferably 0.01 ⁇ m to 10 ⁇ m, more preferably 0.1 ⁇ m to 5 ⁇ m.
  • Examples of the method for forming the protective layer include a method of applying a resin composition dissolved in an organic solvent to form the protective layer, a chemical vapor deposition method, and a method of attaching the molded resin with an adhesive.
  • the components constituting the protective layer include (meth) acrylic resin, en-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, and polyimide.
  • Resin polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, urethane resin, aramid resin, polyamide resin, alkyd resin, epoxy resin, modified silicone resin, fluorine Examples thereof include resins, polycarbonate resins, polyacrylonitrile resins, cellulose resins, Si, C, W, Al 2 O 3 , Mo, SiO 2 , and Si 2 N 4, and two or more of these components may be contained.
  • the protective layer preferably contains a polyol resin, SiO 2 , and Si 2 N 4 .
  • the protective layer preferably contains a (meth) acrylic resin and a fluororesin.
  • the resin composition When the resin composition is applied to form the protective layer, a known method such as a spin coating method, a casting method, a screen printing method, or an inkjet method can be used as the application method of the resin composition.
  • a known method such as a spin coating method, a casting method, a screen printing method, or an inkjet method can be used as the application method of the resin composition.
  • a known organic solvent for example, propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.
  • the protective layer is formed by a chemical vapor deposition method
  • the chemical vapor deposition method is a known chemical vapor deposition method (thermochemical vapor deposition method, plasma chemical vapor deposition method, photochemical vapor deposition method). Can be used.
  • the protective layer is provided with organic particles, inorganic particles, an absorber for light of a specific wavelength (for example, ultraviolet rays, near infrared rays, etc.), a refractive index adjuster, an antioxidant, an adhesive, a surfactant, etc., as necessary. It may contain an agent.
  • organic particles and inorganic particles include polymer particles (eg, silicone resin particles, polystyrene particles, melamine resin particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, and oxynitride. Examples thereof include titanium, magnesium fluoride, hollow silica, silica, calcium carbonate, barium sulfate and the like.
  • a known absorber can be used as the absorber of light having a specific wavelength.
  • the content of these additives can be adjusted as appropriate, but is preferably 0.1% by mass to 70% by mass, more preferably 1% by mass to 60% by mass, based on the total mass of the protective layer.
  • the protective layer described in paragraphs 0073 to 0092 of JP-A-2017-151176 can also be used.
  • the color filter may have a base layer.
  • the base layer can also be formed by using, for example, a composition obtained by removing a colorant such as a pigment from the above-mentioned colored photosensitive composition according to the present disclosure.
  • the surface contact angle of the base layer is preferably 20 ° to 70 ° when measured with diiodomethane. Further, it is preferably 30 ° to 80 ° when measured with water. When the surface contact angle of the base layer is within the above range, the coating property of the resin composition is good.
  • the surface contact angle of the base layer can be adjusted by, for example, adding a surfactant.
  • the method for producing a color filter includes a step of forming a colored photosensitive composition layer on a support using the colored photosensitive composition according to the present disclosure described above, and a colored photosensitive composition by a photolithography method or a dry etching method. It can be manufactured through a step of forming a pattern on a layer. Since the colored photosensitive composition according to the present disclosure can also suppress the generation of development residues, it is particularly effective when a pattern is formed on the colored photosensitive composition layer by a photolithography method to produce a color filter. Is the target.
  • This production method includes a step of forming a colored photosensitive composition layer on a support using the colored photosensitive composition according to the present disclosure, a step of exposing the colored photosensitive composition layer in a pattern, and a colored photosensitive composition. It is preferable to include a step of developing and removing an unexposed portion of the sex composition layer to form a pattern (pixel). If necessary, a step of baking the colored photosensitive composition layer (pre-baking step) and a step of baking the developed pattern (pixels) (post-baking step) may be provided.
  • the colored photosensitive composition layer according to the present disclosure is used to form the colored photosensitive composition layer on the support.
  • the support is not particularly limited and may be appropriately selected depending on the intended use.
  • a glass substrate, a silicon substrate, and the like can be mentioned, and a silicon substrate is preferable.
  • a charge-coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, or the like may be formed on the silicon substrate.
  • CMOS complementary metal oxide semiconductor
  • a black matrix that separates each pixel may be formed on the silicon substrate.
  • the silicon substrate may be provided with a base layer for improving the adhesion with the upper layer, preventing the diffusion of substances, or flattening the surface of the substrate.
  • the base layer is formed by using a composition obtained by removing a colorant from the colored photosensitive composition described in the present specification, a composition containing a resin, a polymerizable compound, a surfactant and the like described in the present specification, and the like. You may.
  • a known method can be used as a method for applying the colored photosensitive composition.
  • a dropping method drop casting
  • a slit coating method for example, a spray method; a roll coating method; a rotary coating method (spin coating); a casting coating method; a slit and spin method; a pre-wet method (for example, JP-A-2009-145395).
  • Methods described in the publication Inkjet (for example, on-demand method, piezo method, thermal method), ejection system printing such as nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, metal mask printing, etc.
  • Various printing methods; transfer method using a mold or the like; nano-imprint method and the like can be mentioned.
  • the method of application to inkjet is not particularly limited, and is, for example, the method shown in "Expandable and usable inkjet-infinite possibilities seen in patents-, published in February 2005, Sumi Betechno Research" (especially from page 115). (Page 133), and the methods described in JP-A-2003-262716, JP-A-2003-185831, JP-A-2003-261827, JP-A-2012-126830, JP-A-2006-169325, and the like. Can be mentioned. Further, regarding the method of applying the colored photosensitive composition, the description of International Publication No. 2017/030174 and International Publication No. 2017/018419 can be referred to, and these contents are incorporated in the present specification.
  • the colored photosensitive composition layer formed on the support may be dried (prebaked).
  • the prebaking temperature is preferably 150 ° C. or lower, more preferably 120 ° C. or lower, and even more preferably 110 ° C. or lower.
  • the lower limit can be, for example, 50 ° C. or higher, or 80 ° C. or higher.
  • the prebaking time is preferably 10 seconds to 300 seconds, more preferably 40 seconds to 250 seconds, and even more preferably 80 seconds to 220 seconds. Pre-baking can be performed on a hot plate, an oven, or the like.
  • the colored photosensitive composition layer is exposed in a pattern (exposure step).
  • the colored photosensitive composition layer can be exposed in a pattern by exposing it through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. As a result, the exposed portion can be cured.
  • Examples of radiation (light) that can be used for exposure include g-line and i-line. Further, light having a wavelength of 300 nm or less (preferably light having a wavelength of 180 nm to 300 nm) can also be used. Examples of the light having a wavelength of 300 nm or less include KrF line (wavelength 248 nm) and ArF line (wavelength 193 nm), and KrF line (wavelength 248 nm) is preferable. Further, a long wave light source having a diameter of 300 nm or more can also be used.
  • pulse exposure is an exposure method of a method of repeatedly irradiating and pausing light in a cycle of a short time (for example, a millisecond level or less).
  • Irradiation dose for example, preferably 0.03J / cm 2 ⁇ 2.5J / cm 2, 0.05J / cm 2 ⁇ 1.0J / cm 2 is more preferable.
  • the oxygen concentration at the time of exposure can be appropriately selected, and in addition to the operation in the atmosphere, for example, in a low oxygen atmosphere having an oxygen concentration of 19% by volume or less (for example, 15% by volume, 5% by volume, or substantially). It may be exposed in an oxygen-free environment), or may be exposed in a high oxygen atmosphere (for example, 22% by volume, 30% by volume, or 50% by volume) in which the oxygen concentration exceeds 21% by volume.
  • the exposure illuminance can be appropriately set, preferably 1,000 W / m 2 to 100,000 W / m 2 (for example, 5,000 W / m 2 , 15,000 W / m 2 , or 35, It can be selected from the range of 000 W / m 2).
  • Oxygen concentration and exposure illuminance may appropriately combined conditions, for example, illuminance 10,000 W / m 2 at an oxygen concentration of 10 vol%, oxygen concentration of 35 vol% can be such illuminance 20,000W / m 2.
  • the unexposed portion of the colored photosensitive composition layer is developed and removed to form a pattern (pixel).
  • the unexposed portion of the coloring composition layer can be developed and removed using a developing solution.
  • the developing solution an organic alkaline developing solution that does not cause damage to the underlying elements and circuits is preferable.
  • the temperature of the developing solution is preferably, for example, 20 ° C to 30 ° C.
  • the development time is preferably 20 seconds to 180 seconds. Further, in order to improve the residue removability, the steps of shaking off the developing solution every 60 seconds and further supplying a new developing solution may be repeated several times.
  • Examples of the developing solution include organic solvents and alkaline developing solutions, and alkaline developing solutions are preferably used.
  • the alkaline developer an alkaline aqueous solution (alkaline developer) obtained by diluting an alkaline agent with pure water is preferable.
  • the alkaline agent include ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxyamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetrabutylammonium hydroxide.
  • Ethyltrimethylammonium hydroxide Ethyltrimethylammonium hydroxide, benzyltrimethylammonium hydroxide, dimethylbis (2-hydroxyethyl) ammonium hydroxide, choline, pyrrole, piperidine, organics such as 1,8-diazabicyclo [5.4.0] -7-undecene.
  • examples thereof include alkaline compounds and inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium silicate and sodium metasilicate.
  • the alkaline agent a compound having a large molecular weight is preferable in terms of environment and safety.
  • the concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001% by mass to 10% by mass, more preferably 0.01% by mass to 1% by mass.
  • the developer may further contain a surfactant.
  • the surfactant include the above-mentioned surfactants, and nonionic surfactants are preferable.
  • the developer may be once produced as a concentrated solution and diluted to a concentration required for use from the viewpoint of convenience of transfer and storage.
  • the dilution ratio is not particularly limited, but can be set in the range of, for example, 1.5 to 100 times. It is also preferable to wash (rinse) with pure water after development.
  • the rinsing is preferably performed by supplying the rinsing liquid to the developed colored photosensitive composition layer while rotating the support on which the developed colored photosensitive composition layer is formed. It is also preferable to move the nozzle for discharging the rinse liquid from the central portion of the support to the peripheral edge of the support. At this time, when moving the nozzle from the central portion of the support to the peripheral portion, the nozzle may be moved while gradually reducing the moving speed. By rinsing in this way, in-plane variation of rinsing can be suppressed. Further, the same effect can be obtained by gradually reducing the rotation speed of the support while moving the nozzle from the central portion to the peripheral portion of the support.
  • Additional exposure treatment and post-baking are post-development curing treatments to complete the curing.
  • the heating temperature in the post-baking is, for example, preferably 100 ° C. to 240 ° C., more preferably 200 to 240 ° C.
  • Post-baking can be performed on the developed film in a continuous or batch manner using a heating means such as a hot plate, a convection oven (hot air circulation type dryer), or a high frequency heater so as to meet the above conditions. ..
  • the light used for the exposure is preferably light having a wavelength of 400 nm or less. Further, the additional exposure process may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
  • a pattern is formed by a dry etching method to manufacture a color filter
  • a colored photosensitive composition layer is formed on the support using the colored photosensitive composition according to the present disclosure, and the entire colored photosensitive composition layer is cured to obtain a cured product.
  • the photoresist layer it is preferable to further perform a prebaking treatment.
  • a prebaking treatment it is desirable to carry out a heat treatment after exposure and a heat treatment (post-baking treatment) after development.
  • a heat treatment after exposure and a heat treatment (post-baking treatment) after development.
  • the description in paragraphs 0010 to 0067 of JP2013-064993A can be referred to, and this content is incorporated in the present specification.
  • the solid-state image sensor according to the present disclosure preferably has the cured product according to the present disclosure and preferably has the color filter according to the present disclosure described above.
  • the configuration of the solid-state image sensor according to the present disclosure is not particularly limited as long as it includes the film according to the present disclosure and functions as a solid-state image sensor, and examples thereof include the following configurations.
  • a solid-state image sensor CCD (charge coupling element) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.
  • a transfer electrode made of polysilicon or the like.
  • the configuration has a color filter on the device protective film.
  • the color filter may have a structure in which each colored pixel is embedded in a space partitioned by a partition wall, for example, in a grid pattern.
  • the partition wall preferably has a lower refractive index than each colored pixel. Examples of an imaging apparatus having such a structure are described in JP2012-227478A, Japanese Patent Application Laid-Open No. 2014-179757, International Publication No. 2018/043654, and US Patent Application Publication No.
  • the image pickup device provided with the solid-state image pickup device according to the present disclosure can be used not only for digital cameras and electronic devices having an image pickup function (mobile phones, etc.), but also for in-vehicle cameras and surveillance cameras. Further, as described in Japanese Patent Application Laid-Open No. 2019-21159, the solid-state image sensor according to the present disclosure is provided with an ultraviolet absorbing layer (UV cut filter) in the structure of the solid-state image sensor, whereby the light resistance of the color filter is reduced. The sex may be improved.
  • UV cut filter ultraviolet absorbing layer
  • the image display device according to the present disclosure preferably has the cured product according to the present disclosure and preferably has the color filter according to the present disclosure described above.
  • Examples of the image display device include a liquid crystal display device and an organic electroluminescence display device.
  • liquid crystal display device is described in, for example, "Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, Kogyo Chosakai Co., Ltd., published in 1994)".
  • the liquid crystal display device to which the present disclosure can be applied is not particularly limited, and for example, it can be applied to various types of liquid crystal display devices described in the above-mentioned "next-generation liquid crystal display technology".
  • % and “parts” mean “mass%” and “parts by mass”, respectively, unless otherwise specified.
  • the molecular weight is the weight average molecular weight (Mw), and the ratio of the constituent units is the molar percentage, except for those specified specifically.
  • the weight average molecular weight (Mw) is a value measured as a polystyrene-equivalent value by a gel permeation chromatography (GPC) method.
  • AM-1 to AM-20 AM-1 to AM-20 described above As AM-9 to AM-14, ADEKA STAB LA-52, LA-57, LA-63P, LA-68, LA-72, and LA-77Y manufactured by ADEKA Corporation were used, respectively.
  • AM-21 Compound produced by the following production method
  • AM-22 Compound produced by the following production method
  • CAM-1 The following compound CAM-2: The following compound
  • AM-21 block copolymer having a hindered amine structure
  • a reactor equipped with a gas introduction tube, a condenser, a stirring blade, and a thermometer was charged with 30 parts of methyl methacrylate, 30 parts of n-butyl methacrylate, 20 parts of hydroxyethyl methacrylate, and 13.2 parts of tetramethylethylenediamine, and nitrogen was poured. While stirring at 50 ° C. for 1 hour, the inside of the system was replaced with nitrogen. Next, 9.3 parts of ethyl bromoisobutyrate, 5.6 parts of cuprous chloride, and 133 parts of methoxypropyl acetate were charged, and the temperature was raised to 110 ° C.
  • a block copolymer (CAM-1) having a hindered amine structure having an amine value of 57 mgKOH / g per solid content was obtained.
  • a block copolymer (AM-21) solution was prepared by adding glycol monomethyl ether acetate.
  • ⁇ Making AM-22 (resin type dispersant)> 70 parts of methyl ethyl ketone (MEK), 76.0 parts of n-butyl acrylate, 2.8 parts of spartein, ethyl bromoisobutyrate 1.
  • MEK methyl ethyl ketone
  • spartein ethyl bromoisobutyrate 1.
  • cuprous chloride was added and the temperature was raised to 75 ° C. to initiate polymerization.
  • the polymerization solution was sampled, and it was confirmed from the solid content of the polymerization that the polymerization yield was 95% or more, and 24.0 parts of N, N-dimethylaminoethyl methacrylate and 30.0 parts of MEK were added. Further, polymerization was carried out. After 2 hours, it was confirmed from the solid content of the polymerization solution that the polymerization yield was 97% or more, and the mixture was cooled to room temperature to terminate the polymerization.
  • 100 parts of the obtained resin solution is diluted with 100 parts of MEK, 60 parts of the cation exchange resin "Diaion PK228LH (manufactured by Mitsubishi Chemical Corporation)" is added, and the mixture is stirred at room temperature for 1 hour, and further, "Kyo” as a neutralizing agent.
  • Ward 500SN manufactured by Kyowa Chemical Industry Co., Ltd. was partially added and stirred for 30 minutes. The residue of the polymerization catalyst was removed by removing the cation exchange resin and the adsorbent by filtration.
  • This dropping solution was dropped into the three-necked flask over 2 hours. After the dropping was completed, the mixture was further heated and stirred at the same temperature for 1 hour. After adding 2.25 parts by mass of V-601, the mixture was heated at the same temperature for 2 hours. Further, 2.25 parts by mass of V-601 was added, the temperature was raised to 90 ° C. and the mixture was heated for 3 hours to complete the polymerization reaction. Next, 35.4 parts by mass of 2-isocyanatoethyl methacrylate (Carens MOI, manufactured by Showa Denko KK) was added to the obtained polymerization reaction product, cooled to 0 ° C., and then zirconium (IV) acetyl.
  • Carens MOI manufactured by Showa Denko KK
  • PGMEA propylene glycol monomethyl ether acetate
  • This dispersion treatment is repeated 10 times, and each dispersion liquid R1 to R12 (red (Red) dispersion liquid), dispersion liquid Y1 (yellow dispersion liquid), and comparative dispersion liquid R1 to R3 (red (Red) dispersion liquid) are respectively. Obtained.
  • PR254 C.I. I. Pigment Red 254
  • PR264 C.I. I. Pigment Red 264
  • PR272 C.I. I. Pigment Red 272
  • PR122 C.I. I. Pigment Red 122 PO71: C.I. I. Pigment Orange 71
  • Resin C1 The following resin, Mw10,000, and the numerical values added to the main chain are molar ratios, and the numerical value in the lower right of the parentheses in ethyleneoxy units represents the average number of repetitions.
  • Photopolymerization initiator F3 A compound having the following structure.
  • Viscosity increase rate (%) [(Viscosity after standing (V1) -Initial viscosity (V0)) / Initial viscosity (V0)] x 100
  • E 15% ⁇ Viscosity increase rate
  • CT-4000 manufactured by Fujifilm Electronics Materials Co., Ltd.
  • CT-4000 is applied on a silicon wafer by the spin coating method so that the film thickness is 0.1 ⁇ m, and heated at 220 ° C. for 1 hour using a hot plate. Formed a stratum.
  • Each colored photosensitive composition is applied onto the silicon wafer with a base layer by a spin coating method, and then heated at 100 ° C. for 2 minutes using a hot plate to obtain a composition layer having a film thickness of 0.5 ⁇ m. rice field.
  • composition layer an i-line stepper FPA-3000i5 + (manufactured by Canon Inc.) was used, and square pixels having a side of 1.1 ⁇ m were arranged in a 4 mm ⁇ 3 mm region on the substrate via a mask pattern. Then, light having a wavelength of 365 nm was irradiated with an exposure amount of 500 mJ / cm 2 for exposure. The exposed composition layer was paddle-developed at 23 ° C. for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide. Then, it was rinsed with water in a spin shower, and further washed with pure water.
  • FPA-3000i5 + manufactured by Canon Inc.
  • the obtained patterns were observed using an optical microscope, and the patterns that were in close contact with each other were counted to evaluate the adhesion.
  • C The patterns that are in close contact are 90% or more and less than 95% of all patterns.
  • D The patterns that are in close contact with each other are 85% or more and less than 90% of all patterns.
  • CT-4000 (manufactured by Fujifilm Electronics Materials Co., Ltd.) is applied on a silicon wafer by the spin coating method so that the film thickness is 0.1 ⁇ m, and heated at 220 ° C. for 1 hour using a hot plate. Formed a stratum.
  • Each colored photosensitive composition was applied onto the silicon wafer with a base layer by a spin coating method, and then heated at 100 ° C. for 2 minutes using a hot plate to obtain a composition layer having a film thickness of 1 ⁇ m.
  • composition layer an i-line stepper FPA-3000i5 + (manufactured by Canon Inc.) was used, and square pixels having a side of 1.1 ⁇ m were arranged in a 4 mm ⁇ 3 mm region on the substrate via a mask pattern. Then, light having a wavelength of 365 nm was irradiated with an exposure amount of 200 mJ / cm 2 for exposure. The exposed composition layer was paddle-developed at 23 ° C. for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide. Then, it was rinsed with water in a spin shower, and further washed with pure water.
  • FPA-3000i5 + manufactured by Canon Inc.
  • Example G57 to Example G72 A colored photosensitive composition was prepared in the same manner as in Example G1 except that the dispersion was changed to that shown in Table 6, and the above evaluation was performed. The evaluation results are shown in Table 6. The content of the pigment in the colored photosensitive compositions of Examples G57 to G72 was 63% by mass with respect to the total solid content of the photosensitive compositions.
  • Example G73 to Example G90 A colored photosensitive composition was prepared in the same manner as in Example G1 except that the types and amounts of the dispersion liquid, the resin, the polymerizable compound, the photopolymerization initiator and the solvent were changed to those shown in Table 7. , The above evaluation was performed.
  • the pigment content in the colored photosensitive compositions of Examples G73 to G90 was 62.6% by mass with respect to the total solid content of the photosensitive compositions.
  • the performance evaluation result was the same as that of Example G9.
  • Resin D7 D-7 (solid content 30%)
  • Resin D9 PGMEA solution of the following resin (solid content 30%)
  • E5 Aronix TO-2349 (manufactured by Toagosei Co., Ltd.)
  • F1 IRGACURE-OXE01 (manufactured by BASF), a compound having the following structure.
  • F2 IRGACURE-OXE02 (manufactured by BASF), a compound having the following structure.
  • F4 IRGACURE 369 (manufactured by BASF), a compound having the following structure.
  • F5 A compound having the following structure.
  • Example G91 to Example G120 A colored photosensitive composition was prepared in the same manner as in Example G1 except that the types and amounts of the dispersion liquid, the resin, the polymerizable compound, the photopolymerization initiator and the solvent were changed to those shown in Table 8. , The above adhesion evaluation and developability evaluation were performed. The evaluation results are shown in Table 8.
  • the “pigment content” in Table 8 represents the content of the pigment with respect to the total solid content of the colored photosensitive composition.
  • Examples R1 to R14, Example Y1, and Comparative Example R1 and Comparative Example R2 A colored photosensitive composition was prepared in the same manner as in Example G1 except that the dispersion was changed to that shown in Table 9, and the above evaluation was performed. The evaluation results are shown in Table 9.
  • the pigment content in the colored photosensitive compositions of Examples R1 to R14, Example Y1, and Comparative Examples R1 and R2 was 63% by mass with respect to the total solid content of the photosensitive compositions. %Met.
  • Example B1 to Example B5, and Comparative Example B1 and Comparative Example B2 A colored photosensitive composition was prepared in the same manner as in Example G1 except that the dispersion was changed to that shown in Table 10, and the above evaluation was performed. The evaluation results are shown in Table 10.
  • the pigment content in the colored photosensitive compositions of Examples B1 to B5, and Comparative Examples B1 and B2 was 63% by mass with respect to the total solid content of the photosensitive compositions. ..
  • the colored photosensitive compositions of Examples were superior in suppressing development residue as compared with the colored photosensitive compositions of Comparative Examples. Further, as shown in Tables 5 to 10 above, the colored photosensitive compositions of Examples were excellent in dispersion stability of the pigment dispersion liquid and adhesion of the obtained cured product.
  • Green pigment dispersion 201 64.2 parts by mass Yellow pigment dispersion 2: 17.6 parts by mass Resin D-7: 1.2 parts by mass Polymerizable compound E1: 0.5 parts by mass Polymerizable compound E6: 0.5 parts Parts by mass Photopolymerization initiator F2: 0.5 parts by mass Surface active agent H1: 0.01 parts by mass Polymerization inhibitor (p-methoxyphenol): 0.01 parts by mass PGMEA: 15.5 parts by mass Cyclohexanone: 1.0 Mass
  • Polymerizable compound E6 The following structure
  • the Green Pigment Dispersion Liquid 201 was changed to the following Green Pigment Dispersion Liquids 202 to 279 to prepare Green Compositions 202 to 279.
  • Green Pigment Dispersion Liquid 201 C I. Pigment Green 58 by 10.0 parts by mass, resin D-1 by 2.5 parts by mass, AM-9 as an amine compound by 0.15 parts by mass, AM-23 by 0.15 parts by mass, PGMEA by 87 parts by mass.
  • a pigment dispersion was prepared by mixing and dispersing the mixed solution consisting of .19 parts by mass with a bead mill (zirconia beads 0.3 mm diameter) for 3 hours.
  • a high-pressure disperser with a decompression mechanism NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) was used to carry out a dispersion treatment at a flow rate of 500 g / min under a pressure of 2,000 kg / cm 3. This dispersion treatment was repeated 10 times to obtain a Green pigment dispersion liquid 201.
  • Green Pigment Dispersion Liquids 202 to 279 The amine compound AM-23 in the Green Pigment Dispersion Liquid 201 was changed to the amine compound in Table 11, the resin D-1 was changed to the resin in Table 11, and PGMEA was changed to Table 11. Green pigment dispersions 202 to 279 were prepared in the same manner as in the preparation of Green pigment dispersion 201, except that the solvent was changed to the inside.
  • Examples G201 to G279 produced colored photosensitive compositions in the same manner as in Example G1, and the above evaluation was performed. The evaluation results were all the same as those of Example G51.
  • a high-pressure disperser with a decompression mechanism NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) was used to carry out a dispersion treatment at a flow rate of 500 g / min under a pressure of 2,000 kg / cm 3. This dispersion treatment was repeated 10 times to obtain a Yellow pigment dispersion liquid 2.
  • Red Composition 101 Preparation of Red Composition 101- The following components were mixed, stirred, and then filtered through a nylon filter (manufactured by Nippon Pole Co., Ltd.) having a pore size of 0.45 ⁇ m to prepare a Red composition.
  • Red pigment dispersion 101 36.8 parts by mass
  • Yellow pigment dispersion 3 26.8 parts by mass
  • Resin D-10 1.2 parts by mass
  • Red Compositions 102-110- Red compositions 102 to 110 were prepared in the same manner as in the preparation of Red composition 101, except that the Red pigment dispersions 101 were changed to the following Red pigment dispersions 102 to 110.
  • a pigment dispersion was prepared by mixing and dispersing a mixed solution consisting of 2 parts by mass with a bead mill (zirconia beads 0.3 mm diameter) for 3 hours.
  • a high-pressure disperser with a decompression mechanism NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) was used to carry out a dispersion treatment at a flow rate of 500 g / min under a pressure of 2,000 kg / cm 3. This dispersion treatment was repeated 10 times to obtain a red pigment dispersion liquid.
  • Red Pigment Dispersion Liquids 102 to 110 Red pigments except that the amine compound CAM-13 of the Red pigment dispersion liquid 201 was changed to the amine compound shown in Table 12 and the resin D-6 was changed to the resin shown in Table 12.
  • the Red pigment dispersions 102 to 110 were prepared in the same manner as in the preparation of the dispersion 101.
  • a high-pressure disperser with a decompression mechanism NANO-3000-10 manufactured by Nippon BEE Co., Ltd. was used to carry out a dispersion treatment at a flow rate of 500 g / min under a pressure of 2,000 kg / cm 3. This dispersion treatment was repeated 10 times to obtain a Yellow pigment dispersion liquid.
  • Example R101 to R110 colored photosensitive compositions were prepared in the same manner as in Example G1, and the above evaluation was performed. The evaluation results were all the same as those of Example R1.
  • Tables 13 to 16 below show details of compounds other than those described above used in Examples G201 to G279 and Examples R101 to R110.
  • Example 301 Fabrication of solid-state image sensor
  • the Green Composition 201 was applied onto a silicon wafer by a spin coating method so that the film thickness after film formation was 0.4 ⁇ m. Then, using a hot plate, it was heated at 100 ° C. for 2 minutes. Next, using an i-line stepper exposure apparatus FPA-3000i5 + (manufactured by Canon Inc.), exposure was performed at 1,000 mJ / cm 2 through a mask with a dot pattern of 1.0 ⁇ m square. Then, paddle development was carried out at 23 ° C. for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH).
  • TMAH tetramethylammonium hydroxide
  • the Green composition was then patterned on a silicon wafer by heating at 200 ° C. for 5 minutes using a hot plate.
  • Red composition 101 and Blue composition 1 were sequentially patterned to form red, green, and blue coloring patterns (Bayer patterns).
  • the Bayer pattern includes one red element, two green elements, and one blue element, as disclosed in US Pat. No. 3,971,065. ) This is a pattern in which a 2 ⁇ 2 array of color filter elements having an element is repeated.
  • the obtained color filter was incorporated into a solid-state image sensor according to a known method. Regardless of which of the colored photosensitive compositions prepared in the examples was used, it was confirmed that the solid-state image sensor had excellent adhesion in the cured film and that a solid-state image sensor having suitable image recognition ability was obtained. rice field.

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JP7392226B2 (ja) 2021-12-17 2023-12-06 東洋インキＳｃホールディングス株式会社 青色カラーフィルタ用感光性着色組成物、カラーフィルタ、およびそれを用いた固体撮像素子並びに液晶表示装置
WO2023136028A1 (ja) * 2022-01-17 2023-07-20 富士フイルム株式会社 着色組成物、膜、構造体、カラーフィルタおよび表示装置
JP7605255B1 (ja) 2023-07-10 2024-12-24 ａｒｔｉｅｎｃｅ株式会社 赤色感光性組成物、膜、カラーフィルタ、固体撮像素子、及び画像表示装置
JP2025010744A (ja) * 2023-07-10 2025-01-23 ａｒｔｉｅｎｃｅ株式会社 赤色感光性組成物、膜、カラーフィルタ、固体撮像素子、及び画像表示装置

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