WO2024014300A1 - Composition de résine, procédé de production d'une composition de résine, dérivé de pigment, film, filtre optique, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image - Google Patents

Composition de résine, procédé de production d'une composition de résine, dérivé de pigment, film, filtre optique, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image Download PDF

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Publication number
WO2024014300A1
WO2024014300A1 PCT/JP2023/024170 JP2023024170W WO2024014300A1 WO 2024014300 A1 WO2024014300 A1 WO 2024014300A1 JP 2023024170 W JP2023024170 W JP 2023024170W WO 2024014300 A1 WO2024014300 A1 WO 2024014300A1
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group
pigment
resin composition
resin
compounds
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PCT/JP2023/024170
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English (en)
Japanese (ja)
Inventor
佑太 奥秋
拓也 鶴田
祐一 安原
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富士フイルム株式会社
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Publication of WO2024014300A1 publication Critical patent/WO2024014300A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/12—Polymers provided for in subclasses C08C or C08F
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters

Definitions

  • the present invention relates to a resin composition containing a pigment and a pigment derivative, and a method for producing the same.
  • the present invention also relates to pigment derivatives, films, optical filters, solid-state imaging devices, and image display devices.
  • CCD charge-coupled device
  • Optical filters such as color filters are manufactured using resin compositions containing coloring materials and resins.
  • a pigment is used as a coloring material, the pigment is dispersed together with a pigment derivative and a resin.
  • Patent Document 1 describes a coloring agent (a) containing a benzimidazolone pigment (a1) having a BET specific surface area of 10 m 2 /g or more and 50 m 2 /g or less, a resin (b), and a solvent (c ) A red colored composition for a color filter is described.
  • an object of the present invention is to provide a resin composition with excellent pigment dispersion stability and a method for producing the same.
  • Another object of the present invention is to provide a pigment derivative, a film, an optical filter, a solid-state image sensor, and an image display device.
  • the present invention provides the following.
  • ⁇ 1> Pigment and A pigment derivative having a BET specific surface area of 2 to 300 m 2 /g by nitrogen adsorption method; resin and A resin composition containing a solvent.
  • the pigment derivative is a particle of a compound having at least one structure selected from the group consisting of a pigment structure and a triazine structure and an acid group or a basic group. .
  • the above dye structures include a diketopyrrolopyrrole structure, a pyrrolopyrrole structure, an azomethine structure, an isoindoline structure, a quinophthalone structure, an azo structure, an anthraquinone structure, a thiazine indigo structure, a quinacridone structure, a benzoindole structure, a phthalocyanine structure, and a dioxazine structure.
  • the resin composition according to ⁇ 2> or ⁇ 3> which has at least one type selected from the group consisting of structures.
  • ⁇ 5> The resin composition according to ⁇ 2> or ⁇ 3>, wherein the dye structure is an azomethine structure.
  • ⁇ 6> The resin composition according to any one of ⁇ 1> to ⁇ 5>, further comprising a photopolymerization initiator and a polymerizable compound.
  • a method for producing a resin composition comprising the step of dispersing a pigment, a pigment derivative having a BET specific surface area of 2 to 300 m 2 /g by nitrogen adsorption method, and a resin in a solvent.
  • the pigment derivative is a particle of a compound having at least one structure selected from the group consisting of a pigment structure and a triazine structure and an acid group or a basic group. manufacturing method.
  • a pigment derivative which is a particle of a compound having at least one structure selected from the group consisting of a pigment structure and a triazine structure and an acid group or a basic group, and which has a BET specific surface area of 2 according to a nitrogen adsorption method. Pigment derivatives with ⁇ 300 m 2 /g. ⁇ 10> The pigment derivative according to ⁇ 9>, which is a dispersion aid.
  • ⁇ 11> A film obtained using the resin composition according to any one of ⁇ 1> to ⁇ 6>.
  • An optical filter having the film according to ⁇ 11>.
  • a solid-state imaging device having the film according to ⁇ 11>.
  • An image display device comprising the film according to ⁇ 11>.
  • the present invention it is possible to provide a resin composition with excellent pigment dispersion stability and a method for producing the same. Further, according to the present invention, a pigment derivative, a film, an optical filter, a solid-state image sensor, and an image display device can be provided.
  • ⁇ is used to include the numerical values described before and after it as a lower limit and an upper limit.
  • the description that does not indicate substituted or unsubstituted includes a group having a substituent (atomic group) as well as a group having no substituent (atomic group).
  • the term "alkyl group” includes not only an alkyl group without a substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
  • exposure includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams, unless otherwise specified.
  • the light used for exposure include actinic rays or radiation such as the bright line spectrum of a mercury lamp, far ultraviolet rays typified by excimer laser, extreme ultraviolet rays (EUV light), X-rays, and electron beams.
  • EUV light extreme ultraviolet rays
  • (meth)acrylate” represents acrylate and/or methacrylate
  • (meth)acrylic represents both acrylic and/or methacrylic
  • (meth)acrylate” represents acrylic and/or methacrylate.
  • Acryloyl refers to either or both of acryloyl and methacryloyl.
  • Me in the structural formula represents a methyl group
  • Et represents an ethyl group
  • Bu represents a butyl group
  • Pr represents a propyl group
  • Ph represents a phenyl group.
  • the weight average molecular weight and number average molecular weight are polystyrene equivalent values measured by GPC (gel permeation chromatography).
  • near-infrared rays refer to light with a wavelength of 700 to 2500 nm.
  • the total solid content refers to the total mass of all components of the composition excluding the solvent.
  • pigment means a coloring material that is difficult to dissolve in a solvent.
  • solubility of the pigment in 100 g of water at 23° C. and 100 g of propylene glycol monomethyl ether acetate at 23° C. is preferably 0.1 g or less, more preferably 0.01 g or less.
  • dye means a coloring material that is easily dissolved in a solvent.
  • process is used not only to refer to an independent process, but also to include a process in which the intended effect of the process is achieved even if the process cannot be clearly distinguished from other processes. .
  • the resin composition of the first aspect of the present invention is pigment and A pigment derivative having a BET specific surface area of 2 to 300 m 2 /g by nitrogen adsorption method; resin and It is characterized by containing a solvent.
  • the resin composition of the second aspect of the present invention is pigment and Particles of a compound having a BET specific surface area of 2 to 300 m 2 /g by a nitrogen adsorption method and having at least one structure selected from the group consisting of a dye structure and a triazine structure and an acid group or a basic group; resin and It is characterized by containing a solvent.
  • the pigment derivative in the resin composition of the first embodiment and the particles in the resin composition of the second embodiment are collectively referred to as specific particles.
  • the resin composition of the present invention has excellent pigment dispersion stability. It is presumed that this effect is obtained due to the following. Since the resin composition of the present invention contains the above-mentioned specific particles having a BET specific surface area of 2 to 300 m 2 /g, the pigment derivative is efficiently adsorbed to the surface of the pigment, and the resin, pigment, and pigment derivative are combined in the resin composition. It is assumed that a strong network can be formed. Therefore, it is assumed that it is possible to suppress the generation of coarse particles due to pigment aggregation during the production of the resin composition, pigment aggregation during the storage of the resin composition, and suppress changes in viscosity over time. be done. It is presumed that for these reasons, a resin composition with excellent pigment dispersion stability could be obtained.
  • the resin composition of the present invention when used to form a pattern by photolithography, it is also possible to suppress the generation of development residues.
  • the reason why such an effect is obtained is presumed to be due to the following. If the specific particles are present as single particles, they tend to adsorb onto the support and remain as development residues even after development, but the resin composition of the present invention Since the specific particles are efficiently adsorbed to the pigment, it is presumed that the specific particles are unlikely to remain as single particles. It is presumed that for these reasons, the generation of development residues can be suppressed.
  • the resin composition of the present invention when used for photolithography, it is preferable that the resin composition of the present invention further contains a polymerizable compound and a photopolymerization initiator. Moreover, it is preferable that the resin contains a resin having an acid group.
  • the resin composition of the present invention is preferably used as a resin composition for optical filters.
  • the optical filter include color filters, near-infrared transmission filters, near-infrared cut filters, etc., and color filters are preferred.
  • the resin composition of the present invention is preferably used for solid-state imaging devices. More specifically, it is preferably used as a resin composition for optical filters used for solid-state imaging devices, and more preferably used as a resin composition for forming colored pixels of color filters used for solid-state imaging devices.
  • color filters include filters that have colored pixels that transmit light of a specific wavelength.
  • colored pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, yellow pixels, etc., preferably red pixels or green pixels, and more preferably red pixels.
  • the colored pixels of the color filter can be formed using a resin composition containing a chromatic pigment.
  • the maximum absorption wavelength of the near-infrared cut filter preferably exists in a wavelength range of 700 to 1800 nm, more preferably exists in a wavelength range of 700 to 1400 nm, and even more preferably exists in a wavelength range of 700 to 1200 nm.
  • the transmittance of the near-infrared cut filter over the entire wavelength range of 400 to 650 nm is preferably 70% or more, more preferably 80% or more, and even more preferably 90% or more.
  • the transmittance at at least one point in the wavelength range of 700 to 1800 nm is preferably 20% or less.
  • the ratio of the absorbance Amax at the maximum absorption wavelength of the near-infrared cut filter to the absorbance A550 at a wavelength of 550 nm is preferably 20 to 500, more preferably 50 to 500. , more preferably from 70 to 450, particularly preferably from 100 to 400.
  • the near-infrared cut filter can be formed using a resin composition containing a near-infrared absorbing pigment.
  • a near-infrared transmission filter is a filter that transmits at least a portion of near-infrared rays.
  • the near-infrared transmission filter may be a filter (transparent film) that transmits both visible light and near-infrared rays, or may be a filter that blocks at least part of visible light and transmits at least part of near-infrared rays. Good too.
  • the near-infrared transmission filter has a maximum transmittance of 20% or less (preferably 15% or less, more preferably 10% or less) in the wavelength range of 400 to 640 nm, and a transmittance in the wavelength range of 1100 to 1300 nm.
  • Preferred examples include filters that satisfy spectral characteristics with a minimum value of 70% or more (preferably 75% or more, more preferably 80% or more).
  • the near-infrared transmission filter is preferably a filter that satisfies any of the following spectral characteristics (1) to (5).
  • 70% or more preferably 75% or more, more preferably 80% or more).
  • the maximum value of transmittance in the wavelength range of 400 to 750 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of transmittance in the wavelength range of 900 to 1500 nm is 70% or more (preferably 75% or more, more preferably 80% or more).
  • the maximum value of transmittance in the wavelength range of 400 to 830 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of transmittance in the wavelength range of 1000 to 1500 nm is 70% or more (preferably 75% or more, more preferably 80% or more).
  • the maximum value of transmittance in the wavelength range of 400 to 950 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of transmittance in the wavelength range of 1100 to 1500 nm is 70% or more (preferably 75% or more, more preferably 80% or more).
  • the maximum value of transmittance in the wavelength range of 400 to 1050 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of transmittance in the wavelength range of 1200 to 1500 nm is 70% or more (preferably 75% or more, more preferably 80% or more).
  • the resin composition of the present invention can also be used for light-shielding films and the like.
  • the solid content concentration of the resin composition of the present invention is preferably 5 to 30% by mass.
  • the lower limit is preferably 7.5% by mass or more, more preferably 10% by mass or more.
  • the upper limit is preferably 25% by mass or less, more preferably 20% by mass or less, and even more preferably 15% by mass or less.
  • the resin composition of the present invention contains a pigment.
  • the pigment include white pigments, black pigments, chromatic pigments, and near-infrared absorbing pigments. Note that in this specification, white pigments include not only pure white pigments but also light gray pigments close to white (for example, grayish white, light gray, etc.).
  • a chromatic pigment is used as the pigment.
  • the number of chromatic pigments may be one, or two or more.
  • a near-infrared absorbing pigment is used as the pigment.
  • the number of near-infrared absorbing pigments may be one type, or two or more types may be included.
  • a combination of two or more chromatic pigments or a pigment containing a black pigment is used as the pigment.
  • the average primary particle diameter of the pigment is preferably 1 to 200 nm.
  • the lower limit is preferably 5 nm or more, more preferably 10 nm or more, even more preferably 20 nm or more, and even more preferably 30 nm or more.
  • the upper limit is preferably 180 nm or less, more preferably 150 nm or less, even more preferably 100 nm or less, even more preferably 90 nm or less, and particularly preferably 80 nm or less.
  • the average primary particle diameter of the pigment can be measured according to the method described in Examples below.
  • the BET specific surface area of the pigment determined by the nitrogen adsorption method is preferably 1 to 300 m 2 /g.
  • the lower limit is preferably 10 m 2 /g or more, more preferably 30 m 2 /g or more.
  • the upper limit is preferably 250 m 2 /g or less, more preferably 200 m 2 /g or less.
  • the BET specific surface area of a pigment can be measured based on the BET method (Brunauer, Emmett and Teller) using a nitrogen adsorption method.
  • the crystallite size determined from the half-width of the peak derived from any crystal plane in the X-ray diffraction spectrum when the CuK ⁇ ray of the pigment is used as the X-ray source is preferably 0.1 nm to 100 nm, and preferably 0.1 nm to 100 nm.
  • the thickness is more preferably 5 nm to 50 nm, even more preferably 1 nm to 30 nm, and particularly preferably 5 nm to 25 nm.
  • Pigments used in the present invention include diketopyrrolopyrrole pigments, pyrrolopyrrole pigments, azomethine pigments, isoindoline pigments, quinophthalone pigments, azo pigments, anthraquinone pigments, thiazine indigo pigments, quinacridone pigments, benzoindole pigments, phthalocyanine pigments and dioxazine pigments. It is preferable that the pigment contains at least one selected from the group consisting of pigments.
  • the chromatic pigment is not particularly limited, and any known chromatic pigment can be used.
  • chromatic pigments include pigments having a maximum absorption wavelength in the wavelength range of 400 to 700 nm. Examples include yellow pigments, orange pigments, red pigments, green pigments, purple pigments, and blue pigments. From the viewpoint of heat resistance, the chromatic pigments are more preferably red pigments, yellow pigments, and blue pigments, and still more preferably red pigments and blue pigments. Specific examples of these include, for example, the following.
  • red pigments examples include diketopyrrolopyrrole compounds, anthraquinone compounds, azo compounds, naphthol compounds, azomethine compounds, xanthene compounds, quinacridone compounds, perylene compounds, thioindigo compounds, and diketopyrrolopyrrole compounds, anthraquinone compounds, azo compounds. is preferable, and a diketopyrrolopyrrole compound is more preferable.
  • red pigments include C. I. (Color Index) Pigment Red 1, 2, 3, 4, 5, 6, 7, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 52:1, 52:2, 53:1, 57:1, 60:1, 63:1, 66, 67, 81:1, 81:2, 81:3, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149, 150, 155, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 200, 202, 206, 207, 208, 209, 210, 216, 220, 224, 226, 242, 246, 254, 255, 264, 269, 270, 272, 279, 291, 294, 295, 296, 297 and the like.
  • red pigment a compound described in paragraph number 0034 of International Publication No. 2022/085485 and a brominated diketopyrrolopyrrole compound described in JP-A No. 2020-085947 can also be used.
  • C. I. Pigment Red 122, 177, 254, 255, 264, 269, 272 are preferred, and C.I. I. Pigment Red 254, 264, and 272 are more preferred, and C.I. I. Pigment Red 254 and 272 are more preferred.
  • the green pigment examples include phthalocyanine compounds and squarylium compounds, preferably phthalocyanine compounds, and more preferably phthalocyanine pigments. Moreover, it is preferable that the green coloring material is a pigment.
  • green pigments include C. I. Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65, 66 and the like.
  • halogenated zinc phthalocyanine pigments have an average number of halogen atoms in one molecule of 10 to 14, an average number of bromine atoms of 8 to 12, and an average of 2 to 5 chlorine atoms.
  • You can also use Specific examples include compounds described in International Publication No. 2015/118720.
  • a compound described in paragraph number 0029 of International Publication No. 2022/085485, an aluminum phthalocyanine compound described in JP 2020-070426, etc. can also be used.
  • C. I. Pigment Green 7, 36, 58, 62, 63 are preferred; I. Pigment Green 36 and 58 are more preferred. used.
  • orange pigments include C.I. I. Pigment Orange 2, 5, 13, 16, 17: 1, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 71, 73, etc. can be mentioned.
  • yellow pigments examples include azo compounds, azomethine compounds, isoindoline compounds, pteridine compounds, quinophthalone compounds, and perylene compounds.
  • Specific examples of yellow pigments include C.I. I. Pigment Yellow 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
  • an azobarbituric acid nickel complex having the following structure can also be used.
  • purple pigments include C. I. Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, 61 and the like.
  • blue pigments include C. I. Pigment Blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 29, 60, 64, 66, 79, 80, 87, 88 etc. It will be done.
  • an aluminum phthalocyanine compound having a phosphorus atom can also be used as the blue pigment.
  • Specific examples include compounds described in paragraph numbers 0022 to 0030 of JP-A No. 2012-247591 and paragraph number 0047 of JP-A No. 2011-157478.
  • Diarylmethane compounds described in Japanese Patent Publication No. 2020-504758 can also be used as the green pigment or blue pigment.
  • Pyrrolopyrrole pigments include those whose crystallite size in the plane direction corresponding to the maximum peak in the X-ray diffraction pattern among the eight ( ⁇ 1 ⁇ 1 ⁇ 1) crystal lattice planes is 140 ⁇ or less. It is also preferable to use Further, the physical properties of the pyrrolopyrrole pigment are also preferably set as described in paragraph numbers 0028 to 0073 of JP-A-2020-097744.
  • Two or more chromatic pigments may be used in combination.
  • the resin composition of the present invention for forming green pixels of a color filter it is preferable to use a green pigment and a yellow pigment together.
  • a red pigment and a yellow pigment together when using the resin composition of the present invention for forming red pixels of a color filter, it is preferable to use a red pigment and a yellow pigment together.
  • black may be formed by a combination of two or more chromatic pigments.
  • examples of such combinations include the following embodiments (1) to (7).
  • the resin composition of the present invention can be used for forming a near-infrared transmitting filter. It can be preferably used as a resin composition.
  • Embodiment containing a red pigment and a blue pigment (2) An embodiment containing a red pigment, a blue pigment, and a yellow pigment.
  • An embodiment containing a red pigment, a blue pigment, a yellow pigment, a purple pigment, and a green pigment An embodiment containing a red pigment, a blue pigment, a yellow pigment, and a green pigment.
  • An embodiment containing a red pigment, a blue pigment, and a green pigment An embodiment containing a red pigment, a blue pigment, and a green pigment.
  • Embodiment containing a yellow pigment and a purple pigment Embodiment containing a yellow pigment and a purple pigment.
  • 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 containing titanium atoms, and more preferably titanium oxide. Further, the white pigment is preferably a particle having a refractive index of 2.10 or more with respect to light with a wavelength of 589 nm. The above-mentioned refractive index is preferably 2.10 to 3.00, more preferably 2.50 to 2.75.
  • titanium oxide described in "Titanium oxide physical properties and applied technology, Manabu Seino, pages 13-45, published June 25, 1991, Gihodo Publishing" can also be used.
  • the white pigment is not only made of a single inorganic substance, but also particles made of a composite with other materials may be used. For example, particles with pores or other materials inside, particles with a large number of inorganic particles attached to a core particle, core and shell composite particles with a core particle made of polymer particles and a shell layer made of inorganic nanoparticles are used. It is preferable.
  • core and shell composite particles consisting of a core particle consisting of a polymer particle and a shell layer consisting of an inorganic nanoparticle for example, the description in paragraphs 0012 to 0042 of JP 2015-047520A can be referred to, This content is incorporated herein.
  • Hollow inorganic particles can also be used as the white pigment.
  • a hollow inorganic particle is an inorganic particle having a structure that has a cavity inside, and is an inorganic particle having a cavity surrounded by an outer shell.
  • Examples of hollow inorganic particles include hollow inorganic particles described in JP2011-075786A, WO2013/061621A, JP2015-164881A, etc., the contents of which are not incorporated herein. It will be done.
  • the black pigment is not particularly limited, and known ones can be used.
  • the inorganic black pigment include carbon black, titanium black, and graphite, with carbon black and titanium black being preferred, and titanium black being more preferred.
  • Titanium black is black particles containing titanium atoms, and lower titanium oxide and titanium oxynitride are preferable.
  • the surface of titanium black can be modified as necessary for the purpose of improving dispersibility, suppressing agglomeration, and the like. For example, it is possible to coat the surface of titanium black with silicon oxide, titanium oxide, germanium oxide, aluminum oxide, magnesium oxide, or zirconium oxide. Furthermore, treatment with a water-repellent substance as disclosed in JP-A No. 2007-302836 is also possible.
  • titanium black has a small primary particle size and an average primary particle size of each particle. Specifically, it is preferable that the average primary particle diameter is 10 to 45 nm.
  • Titanium black can also be used as a dispersion. For example, there may be mentioned a dispersion containing titanium black particles and silica particles, in which the content ratio of Si atoms to Ti atoms in the dispersion is adjusted to a range of 0.20 to 0.50.
  • the descriptions in paragraphs 0020 to 0105 of JP-A-2012-169556 can be referred to, the contents of which are incorporated herein.
  • titanium blacks examples include Titanium Black 10S, 12S, 13R, 13M, 13MC, 13R-N, 13M-T (trade name: manufactured by Mitsubishi Materials Corporation), Tilac D ( Product name: Ako Kasei Co., Ltd.).
  • organic black pigments examples include bisbenzofuranone compounds, azomethine compounds, perylene compounds, and azo compounds.
  • bisbenzofuranone compounds include compounds described in Japanese Patent Application Publication No. 2010-534726, Japanese Patent Application Publication No. 2012-515233, and Japanese Patent Application Publication No. 2012-515234, and for example, as "Irgaphor Black” manufactured by BASF. available.
  • perylene compounds include compounds described in paragraph numbers 0016 to 0020 of JP-A No. 2017-226821, C.I. I. Pigment Black 31, 32, etc.
  • Examples of the azomethine compound include compounds described in JP-A-01-170601 and JP-A-02-034664, and are available as "Chromofine Black A1103" manufactured by Dainichiseika Kaisha, Ltd., for example.
  • the black pigment a black organic pigment described in Japanese Patent No. 6985715, Lumogen Black FK4280, Paliogen Black S0084 (manufactured by BASF) may be used.
  • the near-infrared absorbing pigment is preferably an organic pigment. Further, it is preferable that the near-infrared absorbing pigment has a maximum absorption wavelength in a range of more than 700 nm and less than 1800 nm. Further, the maximum absorption wavelength of the near-infrared absorbing pigment is preferably 1400 nm or less, more preferably 1200 nm or less, and even more preferably 1000 nm or less.
  • A550/Amax which is the ratio of absorbance A550 at a wavelength of 550 nm to absorbance Amax at the maximum absorption wavelength, is preferably 0.1 or less, more preferably 0.05 or less, It is more preferably 0.03 or less, particularly preferably 0.02 or less.
  • the lower limit is not particularly limited, but may be, for example, 0.0001 or more, or 0.0005 or more. If the above-mentioned absorbance ratio is within the above range, a near-infrared absorbing pigment with excellent visible transparency and near-infrared shielding properties can be obtained.
  • Near-infrared absorbing pigments include pyrrolopyrrole compounds, cyanine compounds, squarylium compounds, phthalocyanine compounds, naphthalocyanine compounds, quaterylene compounds, merocyanine compounds, croconium compounds, oxonol compounds, iminium compounds, dithiol compounds, triarylmethane compounds, pyrromethene compounds, Examples include azomethine compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, metal borides, and the like. Specific examples of these include compounds described in paragraph number 0114 of International Publication No. 2022/065215.
  • the compound described in paragraph number 0121 of International Publication No. 2022/065215 the compound described in paragraph number 0121 of International Publication No. 2022/065215, the squarylium compound described in JP 2020-075959, and Korean Published Patent No. 10-2019-0135217 Copper complexes described in the publication, croconic acid compounds described in JP 2021-195515, and near-infrared absorbing dyes described in JP 2022-022070 can also be used.
  • the pigment content in the total solid content of the resin composition is preferably 30 to 80% by mass.
  • the lower limit is preferably 40% by mass or more, more preferably 50% by mass or more.
  • the upper limit is preferably 75% by mass or less, more preferably 70% by mass or less.
  • the content of the chromatic pigment in the pigment contained in the resin composition is preferably 80% by mass or more, and preferably 90% by mass or more.
  • the content is more preferably 95% by mass or more, even more preferably 99% by mass or more.
  • the content of the near-infrared absorbing pigment in the pigment contained in the resin composition is preferably 80% by mass or more, and 90% by mass or more. It is more preferable that the amount is at least 95% by mass, even more preferably at least 99% by mass.
  • the resin composition of the present invention may contain a dye.
  • a dye There are no particular restrictions on the dye, and known dyes can be used. Examples of the dye include chromatic dyes, black dyes, and near-infrared absorbing dyes. As the dye, known dyes can be used.
  • a dye multimer can also be used as the dye. 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 be the same dye structure or may be 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, and even more preferably 20,000 or less.
  • the dye multimer is disclosed in JP-A No. 2011-213925, JP-A 2013-041097, JP-A 2015-028144, JP-A 2015-030742, JP-A 2016-102191, International Publication No. 2016/ Compounds described in No. 031442 and the like can also be used.
  • triarylmethane dye polymers described in Korean Patent Publication No. 10-2020-0028160, xanthene compounds described in JP 2020-117638, and phthalocyanines described in International Publication No. 2020/174991 are used.
  • the isoindoline compound described in International Publication No. 2022/014635, and the aluminum phthalocyanine compound described in International Publication No. 2022/024926 can be used.
  • the pigment or dye may be a rotaxane, and the dye backbone may be used in the cyclic structure of the rotaxane, in the rod-like structure, or in both structures.
  • the content of the dye in the total solid content of the resin composition is preferably 20% by mass or less, more preferably 10% by mass or less, and even more preferably 5% by mass or less. Further, the content of the dye in the resin composition is preferably 60 parts by mass or less, more preferably 40 parts by mass or less, and even more preferably 20 parts by mass or less, based on 100 parts by mass of the pigment. preferable.
  • the resin composition of the present invention does not substantially contain dye.
  • the case where the dye is not substantially contained means that the content of the dye in the total solid content of the resin composition is 0.1% by mass or less, and 0.01% by mass It is preferable that it is below, and it is more preferable that it contains no dye.
  • the resin composition of the first aspect of the present invention contains a pigment derivative having a BET specific surface area of 2 to 300 m 2 /g by nitrogen adsorption method. Further, the resin composition of the second aspect of the present invention has a BET specific surface area of 2 to 300 m 2 /g by nitrogen adsorption method, and has at least one structure selected from the group consisting of a dye structure and a triazine structure; Contains particles of a compound having an acid group or a basic group.
  • the pigment derivative in the resin composition of the first aspect and the particles in the resin composition of the second aspect are collectively referred to as specific particles.
  • a dispersion aid is a material for improving the dispersibility of pigments in a resin composition.
  • the specific particles used in the resin composition of the first aspect are at least one type selected from the group consisting of a pigment structure and a triazine structure.
  • the particles are preferably particles of a compound having a structure of 1 and an acid group or a basic group.
  • the BET specific surface area of the specific particles determined by the nitrogen adsorption method is 2 to 300 m 2 /g.
  • the lower limit of the BET specific surface area of the specific particles is preferably 3 m 2 /g or more, more preferably 5 m 2 /g or more.
  • the upper limit of the BET specific surface area of the specific particles is preferably 250 m 2 /g or less, more preferably 200 m 2 /g or less, even more preferably 150 m 2 /g or less, and 100 m 2 /g or less. It is even more preferable that The BET specific surface area of a specific particle is a value measured based on the BET method (Brunauer, Emmett, and Teller) using a nitrogen adsorption method.
  • the average primary particle diameter of the specific particles is preferably 5 to 200 nm.
  • the upper limit is preferably 150 nm or less, more preferably 100 nm or less.
  • the lower limit is preferably 10 nm or more, more preferably 20 nm or more.
  • the average primary particle diameter of specific particles can be measured according to the method described in Examples below.
  • the difference between the average primary particle diameter of the specific particles contained in the resin composition and the average primary particle diameter of the pigment is preferably 0 to 100 nm.
  • the upper limit is preferably 50 nm or less, more preferably 30 nm or less.
  • the lower limit is preferably 2 nm or more, more preferably 5 nm or more. If the difference between the average primary particle diameter of the specific particles and the average primary particle diameter of the pigment is within the above range, the dispersion stability of the pigment can be further improved.
  • the specific particles are particles of a compound having at least one structure selected from the group consisting of a dye structure and a triazine structure and an acid group or a basic group
  • the dye structure possessed by the specific particles is a diketopyrrolodine structure.
  • It is preferably an azomethine structure, and more preferably an azomethine structure.
  • the acid group possessed by the specific particles includes a carboxy group
  • examples include a sulfo group, a phosphoric acid group, a boronic acid group, an imide acid group, and salts thereof.
  • Atoms or atomic groups constituting the salt include alkali metal ions (Li + , Na + , K + , etc.), alkaline earth metal ions (Ca 2+ , Mg 2+ , etc.), ammonium ions, imidazolium ions, pyridinium ions, Examples include phosphonium ions.
  • the imide acid group is preferably a group represented by -SO 2 NHSO 2 R X1 , -CONHSO 2 R X2 , -CONHCOR X3 or -SO 2 NHCOR , or -SO 2 NHCOR X4 is more preferred, and -SO 2 NHSO 2 R X1 or -CONHSO 2 R X2 is even more preferred.
  • R X1 to R X4 each independently represent an alkyl group or an aryl group.
  • the alkyl group and aryl group represented by R X1 to R X4 may have a substituent.
  • the substituent is preferably a halogen atom, more preferably a fluorine atom.
  • R X1 to R X4 are each independently preferably an alkyl group containing a fluorine atom or an aryl group containing a fluorine atom, and more preferably an alkyl group containing a fluorine atom.
  • the number of carbon atoms in the alkyl group containing a fluorine atom is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
  • the number of carbon atoms in the aryl group containing a fluorine atom is preferably 6 to 20, more preferably 6 to 12, and even more preferably 6.
  • the specific particles are particles of a compound having at least one structure selected from the group consisting of a dye structure and a triazine structure and an acid group or a basic group
  • the basic group possessed by the specific particles is an amino group.
  • atoms or atomic groups constituting the salt include hydroxide ions, halogen ions, carboxylate ions, sulfonate ions, and phenoxide ions.
  • Examples of the amino group include a group represented by -NR x11 R x12 and a cyclic amino group.
  • R x11 and R x12 each independently represent a hydrogen atom, an alkyl group, or an aryl group, and preferably an alkyl group. That is, the amino group is preferably a dialkylamino group.
  • the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
  • the alkyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear.
  • the alkyl group may have a substituent. Examples of the substituent include the substituent T described below.
  • the number of carbon atoms in the aryl group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12.
  • the aryl group may have a substituent. Examples of the substituent include the substituent T described below.
  • cyclic amino group examples include a pyrrolidine group, a piperidine group, a piperazine group, and a morpholine group. These groups may further have a substituent.
  • the specific particles are particles of a compound having a dye structure and an acid group or a basic group
  • the specific particles are preferably particles of a compound represented by formula (B1).
  • P represents a dye structure
  • L represents a single bond or an n+1-valent linking group
  • X represents an acid group or basic group
  • m represents an integer of 1 or more
  • n represents 1 or more.
  • the plurality of L's and X's may be different from each other, and when n is 2 or more, the plurality of X's may be different from each other.
  • the dye structures represented by P in formula (B1) include a diketopyrrolopyrrole structure, a pyrrolopyrrole structure, an azomethine structure, an isoindoline structure, a quinophthalone structure, an azo structure, an anthraquinone structure, a thiazine indigo structure, a quinacridone structure, a benzoindole structure, A phthalocyanine structure or a dioxazine structure is preferable, and an azomethine structure is more preferable.
  • the n+1-valent linking group represented by L in formula (B1) is an aliphatic hydrocarbon group, an aromatic hydrocarbon group, a heterocyclic group, -O-, -S-, -CO-, -COO-, -OCO- , -SO 2 -, -NR L -, -NR L CO-, -CONR L -, -NR L SO 2 -, -SO 2 NR L -, and combinations thereof.
  • R L represents a hydrogen atom, an alkyl group or an aryl group.
  • the number of carbon atoms in the aliphatic hydrocarbon group is preferably 1 to 20, more preferably 2 to 20, even more preferably 2 to 10, particularly preferably 2 to 5.
  • the aliphatic hydrocarbon group may be linear, branched, or cyclic. Furthermore, the cyclic aliphatic hydrocarbon group may be either monocyclic or polycyclic.
  • the aromatic hydrocarbon group preferably has 6 to 18 carbon atoms, more preferably 6 to 14 carbon atoms, and even more preferably 6 to 10 carbon atoms.
  • the aromatic hydrocarbon group is preferably a monocyclic or fused ring aromatic hydrocarbon group having 2 to 4 condensed rings.
  • the aromatic hydrocarbon group is preferably a benzene ring group.
  • the heterocyclic group is preferably a single ring or a condensed ring having 2 to 4 condensed rings. The number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3.
  • the heteroatom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
  • the number of carbon atoms constituting the ring of the heterocyclic group is preferably 3 to 30, more preferably 3 to 18, and even more preferably 3 to 12.
  • the heterocyclic group is preferably a triazine ring group.
  • the aliphatic hydrocarbon group, aromatic hydrocarbon group and heterocyclic group may have a substituent. Examples of the substituent include the substituent T described below.
  • the number of carbon atoms in the alkyl group represented by R L is preferably 1 to 20, more preferably 1 to 15, and even more preferably 1 to 8.
  • the alkyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear.
  • the alkyl group represented by R L may further have a substituent. Examples of the substituent include the substituent T described below.
  • the number of carbon atoms in the aryl group represented by R L is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12.
  • the aryl group represented by R L may further have a substituent. Examples of the substituent include the substituent T described below.
  • Examples of the acid group and basic group represented by X in formula (B1) include the acid groups and basic groups described above.
  • n in formula (B1) is 1 or 2.
  • the specific particles are particles of a compound having a triazine structure and an acid group or a basic group
  • examples of such specific particles include particles of a compound having a group represented by formula (A1).
  • * represents a bond
  • Ya 1 and Ya 2 each independently represent -N(Ra 1 )- or -O-
  • Ra 1 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aryl group
  • B 1 and B 2 each independently represent a hydrogen atom or a substituent.
  • Ya 1 and Ya 2 in formula (A1) each independently represent -N(Ra 1 )- or -O-, and preferably -N(Ra 1 )-.
  • Ra 1 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, or an aryl group, preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
  • the number of carbon atoms in the alkyl group represented by Ra 1 is preferably 1 to 20, more preferably 1 to 15, and even more preferably 1 to 8.
  • the alkyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear.
  • the alkyl group represented by Ra 1 may further have a substituent. Examples of the substituent include the substituent T described below.
  • the alkenyl group represented by Ra 1 preferably has 2 to 20 carbon atoms, more preferably 2 to 12 carbon atoms, and particularly preferably 2 to 8 carbon atoms.
  • the alkenyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear.
  • the alkenyl group represented by Ra 1 may further have a substituent. Examples of the substituent include the substituent T described below.
  • the number of carbon atoms in the alkynyl group represented by Ra 1 is preferably 2 to 40, more preferably 2 to 30, particularly preferably 2 to 25.
  • the alkynyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear.
  • the alkynyl group represented by Ra 1 may further have a substituent.
  • substituents include the substituent T described below.
  • the number of carbon atoms in the aryl group represented by Ra 1 is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12.
  • the aryl group represented by Ra 1 may further have a substituent. Examples of the substituent include the substituent T described below.
  • B 1 and B 2 in formula (A1) each independently represent a hydrogen atom or a substituent.
  • substituents include the substituent T described later, with alkyl groups, aryl groups, and heterocyclic groups being preferred, and aryl groups and heterocyclic groups being more preferred.
  • a preferred embodiment is one in which one of B 1 and B 2 is a heterocyclic group and the other is an aryl group.
  • the heterocyclic group is preferably a nitrogen-containing heterocyclic group, and more preferably a benzimidazolone group.
  • the specific particles are particles of a compound having a triazine structure and an acid group or a basic group
  • the specific particles are preferably particles of a compound represented by the following formula (b1). A 1 -L 1 -Z 1 ...(b1)
  • a 1 in formula (b1) represents a group represented by formula (A1) above.
  • L 1 in formula (b1) represents a single bond or a divalent linking group, and is preferably a divalent linking group.
  • the divalent linking group represented by L 1 includes an alkylene group, an arylene group, a heterocyclic group, -O-, -NR L1 -, -NHCO-, -CONH-, -OCO-, -COO-, -CO- , -SO 2 NH-, -SO 2 - and combinations thereof.
  • the alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms, even more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 5 carbon atoms.
  • the alkylene group may be linear, branched, or cyclic, preferably linear or branched, and particularly preferably linear.
  • the number of carbon atoms in the arylene group is preferably 6 to 30, more preferably 6 to 15.
  • the arylene group is a phenylene group.
  • R L1 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, or an aryl group, preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
  • the preferred ranges of the alkyl group, alkenyl group, alkynyl group, and aryl group represented by R L1 are the same as the ranges described as the preferred ranges of the alkyl group, alkenyl group, alkynyl group, and aryl group of Ra 1 .
  • the divalent linking group represented by L 1 is preferably a group represented by the following formula (L1). -L 1A -L 1B -L 1C - ... (L1)
  • L 1A and L 1C are each independently -O-, -NR L1 -, -NHCO-, -CONH-, -OCO-, -COO-, -CO-, -SO 2 NH-, or , -SO 2 -
  • L 1B represents a single bond or a divalent linking group.
  • the divalent linking group represented by L 1B is an alkylene group, an arylene group, a single bond between an alkylene group and an arylene group, or -O-, -NR L1 -, -NHCO-, -CONH-, -OCO-, -COO -, -CO-, -SO 2 NH-, -SO 2 - and combinations thereof, groups bonded to each other, alkylene groups or arylene groups to -O-, -NR L1 -, -NHCO- , -CONH-, -OCO-, -COO-, -CO-, -SO 2 NH-, -SO 2 -, and a group bonded through a group consisting of a combination thereof.
  • L 1 examples include groups having the following structure.
  • Z 1 in formula (b1) represents a group having an acid group or a basic group.
  • Examples of the acid group and basic group include the groups mentioned above.
  • Z 1 in formula (b1) is preferably a group represented by formula (Z1) or a group represented by formula (Z10).
  • Yz 1 represents -N(Ry 1 )- or -O-
  • Ry 1 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aryl group
  • Lz 1 represents a divalent linking group
  • Rz 1 and Rz 2 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aryl group
  • Rz 1 and Rz 2 may be bonded via a divalent group to form a ring
  • m represents an integer from 1 to 5.
  • * represents a bond
  • Lc 1 and Lc 2 each independently represent a single bond or a linking group
  • Rc 1 and Rc 2 each independently represent a substituent
  • Rc 1 and Rc 2 At least one of 2 represents an acid group or a basic group.
  • Yz 1 represents -N(Ry 1 )- or -O-, and preferably -N(Ry 1 )-.
  • Ry 1 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, or an aryl group, preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
  • the preferred ranges of the alkyl group, alkenyl group, alkynyl group, and aryl group represented by Ry 1 are the same as the ranges described as the preferred ranges of the alkyl group, alkenyl group, alkynyl group, and aryl group of Ra 1 .
  • the divalent linking group represented by Lz 1 includes an alkylene group, an arylene group, a heterocyclic group, -O-, -NR L1 -, -NHCO-, -CONH-, -OCO-, - Examples include COO-, -CO-, -SO 2 NH-, -SO 2 -, and combinations thereof, with alkylene groups being preferred.
  • the alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms, even more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 5 carbon atoms.
  • the alkylene group may be linear, branched, or cyclic, preferably linear or branched, and particularly preferably linear.
  • Rz 1 and Rz 2 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, or an aryl group, preferably an alkyl group or an aryl group, and an alkyl group. is more preferable.
  • the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 5, even more preferably 1 to 3, particularly preferably 1 or 2.
  • the alkyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear.
  • the alkenyl group preferably has 2 to 10 carbon atoms, more preferably 2 to 8 carbon atoms, and particularly preferably 2 to 5 carbon atoms.
  • the alkenyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear.
  • the number of carbon atoms in the alkynyl group is preferably 2 to 10, more preferably 2 to 8, particularly preferably 2 to 5.
  • the alkynyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear.
  • the number of carbon atoms in the aryl group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12.
  • Rz 1 and Rz 2 may be bonded via a divalent group to form a ring.
  • divalent groups include -CH 2 -, -O-, and -SO 2 -.
  • Specific examples of the ring formed by Rz 1 and Rz 2 via a divalent group include the following.
  • m represents an integer of 1 to 5, preferably 1 to 4, more preferably 1 to 3, even more preferably 2 or 3, and particularly preferably 2.
  • the group represented by formula (Z1) is preferably a group represented by formula (Z2) below.
  • * represents a bond
  • Yz 2 and Yz 3 each independently represent -N(Ry 2 )- or -O-
  • Ry 2 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aryl group
  • Lz 2 and Lz 3 each independently represent a divalent linking group
  • Rz 3 to Rz 6 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, or an aryl group
  • Rz 3 and Rz 4 and Rz 5 and Rz 6 may be bonded to each other via a divalent group to form a ring.
  • Yz 2 and Yz 3 in formula (Z2) have the same meaning as Yz 1 in formula (Z1), and the preferred ranges are also the same.
  • Ry 2 represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, or an aryl group, preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
  • the preferred ranges of the alkyl group, alkenyl group, alkynyl group, and aryl group represented by Ry 2 are the same as the ranges described as the preferred ranges of the alkyl group, alkenyl group, alkynyl group, and aryl group of Ra 1 .
  • Lz 2 and Lz 3 in formula (Z2) have the same meanings as Lz 1 in formula (Z1), and the preferred ranges are also the same.
  • Rz 3 to Rz 6 in formula (Z2) have the same meanings as Rz 1 and Rz 2 in formula (Z1), and their preferred ranges are also the same.
  • Lc 1 and Lc 2 each independently represent a single bond or a linking group, and preferably a divalent linking group.
  • the divalent linking group include an alkylene group, an arylene group, -O-, -NR L1 -, -NHCO-, -CONH-, -OCO-, -COO-, -CO-, -SO 2 NH-, - Includes SO 2 - and combinations thereof.
  • the alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 15 carbon atoms, even more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 5 carbon atoms.
  • the alkylene group may be linear, branched, or cyclic, preferably linear or branched, and particularly preferably linear.
  • the number of carbon atoms in the arylene group is preferably 6 to 30, more preferably 6 to 15.
  • the arylene group is a phenylene group.
  • R L1 represents a hydrogen atom, an alkyl group, or an aryl group, preferably a hydrogen atom or an alkyl group, and more preferably a hydrogen atom.
  • the number of carbon atoms in the alkyl group represented by R L1 is preferably 1 to 20, more preferably 1 to 15, even more preferably 1 to 8.
  • the alkyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear.
  • the alkyl group represented by R L1 may further have a substituent.
  • substituents include the substituent T described below.
  • the number of carbon atoms in the aryl group represented by R L1 is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12.
  • the aryl group represented by R L1 may further have a substituent. Examples of the substituent include the substituent T described below.
  • Rc 1 and Rc 2 each independently represent a substituent.
  • the substituent include an alkyl group, an aryl group, a heterocyclic group, a hydroxy group, an acid group, and a basic group.
  • at least one of Rc 1 and Rc 2 represents an acid group or a basic group.
  • At least one of Rc 1 and Rc 2 is preferably a basic group, and more preferably both Rc 1 and Rc 2 are basic groups.
  • the acid group and basic group include those mentioned above.
  • the number of carbon atoms in the alkyl group is preferably 1 to 30, more preferably 1 to 15, even more preferably 1 to 8.
  • the alkyl group may be linear, branched, or cyclic, preferably linear or branched, and more preferably linear.
  • the number of carbon atoms in the aryl group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12.
  • the heterocyclic group may be a single ring or a condensed ring.
  • the heterocyclic group is preferably a single ring or a condensed ring having 2 to 4 condensed rings.
  • the number of heteroatoms constituting the ring of the heterocyclic group is preferably 1 to 3.
  • the heteroatom constituting the ring of the heterocyclic group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
  • the number of carbon atoms constituting the ring of the heterocyclic group is preferably 3 to 30, more preferably 3 to 18, and even more preferably 3 to 12.
  • the alkyl group, aryl group, and heterocyclic group may further have a substituent. Examples of the substituent include the substituent T described below.
  • substituent T examples include the following groups.
  • Halogen atom e.g. fluorine atom, chlorine atom, bromine atom, iodine atom
  • alkyl group preferably an alkyl group having 1 to 30 carbon atoms
  • alkenyl group preferably an alkenyl group having 2 to 30 carbon atoms
  • alkynyl group preferably an alkynyl group having 2 to 30 carbon atoms
  • an aryl group preferably an aryl group having 6 to 30 carbon atoms
  • a heteroaryl group preferably a heteroaryl group having 1 to 30 carbon atoms
  • an alkoxy group preferably (alkoxy group having 1 to 30 carbon atoms)
  • aryloxy group preferably aryloxy group having 6 to 30 carbon atoms
  • heteroaryloxy group preferably heteroaryloxy group having 1 to 30 carbon atoms
  • acyl group preferably is an acyl group having 2 to 30 carbon atoms
  • specific particles include compounds described in the Examples described below, compounds described in JP-A-56-118462, compounds described in JP-A-63-264674, and JP-A-01-217077.
  • Compounds described in JP-A-03-009961, compounds described in JP-A-03-026767, compounds described in JP-A-03-153780, compounds described in JP-A-03-045662 Compounds described in JP-A-04-285669, compounds described in JP-A-06-145546, compounds described in JP-A-06-212088, compounds described in JP-A-06-240158 , compounds described in JP-A-10-030063, compounds described in JP-A-10-195326, compounds described in paragraph numbers 0086 to 0098 of WO 2011/024896, WO 2012/102399 Compounds described in paragraph numbers 0063 to 0094 of , compounds described in paragraph number 0082 of International Publication No.
  • the content of the specific particles is preferably 1 to 70 parts by mass based on 100 parts by mass of the pigment.
  • the lower limit is preferably 2 parts by mass or more, more preferably 3 parts by mass or more, and even more preferably 5 parts by mass or more.
  • the upper limit is preferably 60 parts by mass or less, more preferably 50 parts by mass or less, and even more preferably 40 parts by mass or less. Only one type of specific particles may be used, or two or more types may be used in combination. When two or more types are used in combination, it is preferable that the total amount is within the above range.
  • the resin composition of the present invention contains a resin.
  • the resin is blended, for example, for use in dispersing pigments in a resin composition or for use as a binder.
  • a resin used mainly for dispersing pigments is also referred to as a dispersant.
  • this use of the resin is just an example, and the resin can also be used for purposes other than this use.
  • the resin examples include (meth)acrylic resin, epoxy resin, (meth)acrylamide resin, ene thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, and polyarylene.
  • examples include ether phosphine oxide resin, polyimide resin, polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, and siloxane resin.
  • the resins include the resin described in the examples of International Publication No.
  • Polyisocyanate resin resin described in JP 2020-122052, resin described in JP 2020-111656, resin described in JP 2020-139021, JP 2017-138503 Resin containing a structural unit having a ring structure in the main chain and a structural unit having a biphenyl group in the side chain described in JP 2020-186373, paragraphs 0199 to 0233, JP 2020-186325 Alkali-soluble resins described in the publication, resins represented by formula 1 described in Korean Patent Publication No. 10-2020-0078339, copolymers containing epoxy groups and acid groups described in International Publication No. 2022/030445 You can also use
  • the weight average molecular weight (Mw) of the resin is preferably 3,000 to 2,000,000.
  • the upper limit is preferably 1,000,000 or less, more preferably 500,000 or less.
  • the lower limit is preferably 4000 or more, more preferably 5000 or more.
  • the resin it is preferable to use a resin having acid groups.
  • the acid group include a carboxy group, a phosphoric acid group, a sulfo group, and a phenolic hydroxy group.
  • the acid value of the resin having acid groups is preferably 30 to 500 mgKOH/g.
  • the lower limit is more preferably 40 mgKOH/g or more, particularly preferably 50 mgKOH/g or more.
  • the upper limit is more preferably 400 mgKOH/g or less, even more preferably 300 mgKOH/g or less, and particularly preferably 200 mgKOH/g or less.
  • the weight average molecular weight (Mw) of the resin having acid groups is preferably 5,000 to 100,000, more preferably 5,000 to 50,000. Further, the number average molecular weight (Mn) of the resin having acid groups is preferably 1,000 to 20,000.
  • the resin having an acid group preferably contains a repeating unit having an acid group in its side chain, and more preferably contains 5 to 70 mol% of repeating units having an acid group in its side chain based on the total repeating units of the resin.
  • the upper limit of the content of repeating units having acid groups in their side chains is preferably 50 mol% or less, more preferably 30 mol% or less.
  • the lower limit of the content of repeating units having acid groups in their side chains is preferably 10 mol% or more, more preferably 20 mol% or more.
  • a resin having a basic group can also be used.
  • the resin having a basic group is preferably a resin containing a repeating unit having a basic group in its side chain, and a resin having a repeating unit having a basic group in its side chain and a repeating unit not containing a basic group.
  • a polymer is more preferable, and a block copolymer having a repeating unit having a basic group in its side chain and a repeating unit not containing a basic group is even more preferable.
  • a resin having a basic group can also be used as a dispersant.
  • the amine value of the resin having a basic group is preferably 5 to 300 mgKOH/g.
  • the lower limit is preferably 10 mgKOH/g or more, more preferably 20 mgKOH/g or more.
  • the upper limit is preferably 200 mgKOH/g or less, more preferably 100 mgKOH/g or less.
  • resins having basic groups include DISPERBYK-161, 162, 163, 164, 166, 167, 168, 174, 182, 183, 184, 185, 2000, 2001, 2050, 2150, 2163, 2164, BYK-LPN6919 (manufactured by BYK Chemie), Solsperse 11200, 13240, 13650, 13940, 24000, 26000, 28000, 32000, 32500, 32550, 32600, 33000, 34750, 35100, 35200, 37500, 385 00, 39000, 53095, 56000, 7100 (all manufactured by Japan Lubrizol), Efka PX 4300, 4330, 4046, 4060, 4080 (all manufactured by BASF), and the like.
  • the resin having a basic group is the block copolymer (B) described in paragraph numbers 0063 to 0112 of JP2014-219665A, and the block copolymer (B) described in paragraphs 0046 to 0076 of JP2018-156021A. It is also possible to use block copolymer A1, a vinyl resin having a basic group described in paragraphs 0150 to 0153 of JP-A No. 2019-184763, the contents of which are incorporated herein.
  • the content of the resin having a basic group is preferably 20 to 500 parts by mass per 100 parts by mass of the resin having an acid group.
  • the amount is preferably 30 to 300 parts by weight, more preferably 50 to 200 parts by weight.
  • the resin is derived from a monomer component containing a compound represented by the following formula (ED1) and/or a compound represented by the following formula (ED2) (hereinafter, these compounds may be referred to as "ether dimer”). It is also preferable to use a resin containing repeating units.
  • R 1 and R 2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.
  • R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms.
  • R 1 represents a hydrogen atom or a methyl group
  • R 21 and R 22 each independently represent an alkylene group
  • n represents an integer of 0 to 15.
  • the alkylene group represented by R 21 and R 22 preferably has 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms, even more preferably 1 to 3 carbon atoms, and particularly 2 or 3 carbon atoms.
  • n represents an integer of 0 to 15, preferably an integer of 0 to 5, more preferably an integer of 0 to 4, even more preferably an integer of 0 to 3.
  • Examples of the compound represented by formula (X) include ethylene oxide- or propylene oxide-modified (meth)acrylate of paracumylphenol.
  • Commercially available products include Aronix M-110 (manufactured by Toagosei Co., Ltd.).
  • the resin it is also preferable to use a resin having a crosslinkable group.
  • the crosslinkable group include ethylenically unsaturated bond-containing groups and cyclic ether groups.
  • the ethylenically unsaturated bond-containing group include a vinyl group, a styrene group, a (meth)allyl group, and a (meth)acryloyl group.
  • the cyclic ether group include an epoxy group and an oxetanyl group, with an epoxy group being preferred.
  • the epoxy group may be a cycloaliphatic epoxy group. Note that the alicyclic epoxy group means a monovalent functional group having a cyclic structure in which an epoxy ring and a saturated hydrocarbon ring are condensed.
  • the resin it is also preferable to use a resin having an aromatic carboxy group (hereinafter also referred to as resin Ac).
  • the aromatic carboxy group may be included in the main chain of the repeating unit, or may be included in the side chain of the repeating unit.
  • the aromatic carboxy group is preferably contained in the main chain of the repeating unit.
  • an aromatic carboxy group refers to a group having a structure in which one or more carboxy groups are bonded to an aromatic ring.
  • the number of carboxy groups bonded to the aromatic ring is preferably 1 to 4, more preferably 1 to 2.
  • the resin Ac is preferably a resin containing at least one type of repeating unit selected from a repeating unit represented by formula (Ac-1) and a repeating unit represented by formula (Ac-2).
  • Ar 1 represents a group containing an aromatic carboxy group
  • L 1 represents -COO- or -CONH-
  • L 2 represents a divalent linking group
  • Ar 10 represents a group containing an aromatic carboxy group
  • L 11 represents -COO- or -CONH-
  • L 12 represents a trivalent linking group
  • P 10 represents a polymer Represents a chain.
  • Examples of the group containing an aromatic carboxy group represented by Ar 1 in formula (Ac-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 anhydride and aromatic tetracarboxylic anhydride include compounds having the following structures.
  • Q 1 is a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2 -, -C(CF 3 ) 2 -, represented by the following formula (Q-1). or a group represented by the following formula (Q-2).
  • the aromatic carboxy group-containing group represented by Ar 1 may have a crosslinkable group.
  • the crosslinkable group is preferably an ethylenically unsaturated bond-containing group and a cyclic ether group, and more preferably an ethylenically unsaturated bond-containing group.
  • Specific examples of the group containing an aromatic carboxy group represented by Ar 1 include a group represented by formula (Ar-11), a group represented by formula (Ar-12), and a group represented by formula (Ar-13). Examples include groups such as
  • n1 represents an integer of 1 to 4, preferably 1 or 2, and more preferably 2.
  • n2 represents an integer of 1 to 8, preferably an integer of 1 to 4, more preferably 1 or 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 or 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- Represents a group represented by 1) or a group represented by the above formula (Q-2).
  • *1 represents the bonding position with L 1 .
  • L 1 represents -COO- or -CONH-, and preferably represents -COO-.
  • the divalent linking group represented by L 2 in formula (Ac-1) includes an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and these. Examples include groups combining two or more of the following.
  • the alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and still more preferably 1 to 15 carbon atoms.
  • the alkylene group may be linear, branched, or cyclic.
  • the number of carbon atoms in the arylene group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 10.
  • the alkylene group and arylene group may have a substituent.
  • the divalent linking group represented by L 2 is preferably a group represented by -L 2a -O-.
  • L 2a is an alkylene group; an arylene group; a group combining an alkylene group and an arylene group; at least one selected from an alkylene group and an arylene group, and -O-, -CO-, -COO-, -OCO-, Examples include a group combining at least one selected from -NH- and -S-, and an alkylene group is preferred.
  • the alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and still more preferably 1 to 15 carbon atoms.
  • the alkylene group may be linear, branched, or cyclic.
  • the alkylene group and arylene group may have a substituent. Examples of the substituent include a hydroxy group.
  • the aromatic carboxy group-containing group represented by Ar 10 in formula (Ac-2) has the same meaning as Ar 1 in formula (Ac-1), and the preferred range is also the same.
  • L 11 represents -COO- or -CONH-, preferably -COO-.
  • the trivalent linking group represented by L 12 in formula (Ac-2) includes a hydrocarbon group, -O-, -CO-, -COO-, -OCO-, -NH-, -S-, and these two groups. Examples include groups that combine more than one species.
  • Examples of the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The number of carbon atoms in 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 aromatic hydrocarbon 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 hydrocarbon group may have a substituent. Examples of the substituent include a hydroxy group.
  • the trivalent linking group represented by L 12 is preferably a group represented by formula (L12-1), more preferably a group represented by formula
  • L 12b represents a trivalent linking group
  • X 1 represents S
  • *1 represents the bonding position with L 11 of formula (Ac-2)
  • *2 represents formula ( It represents the bonding position of Ac-2) with P10 .
  • the trivalent linking group represented by L 12b is a hydrocarbon group; a hydrocarbon group, and at least one kind selected from -O-, -CO-, -COO-, -OCO-, -NH-, and -S-.
  • a hydrocarbon group or a group consisting of a hydrocarbon group and -O- is preferable.
  • L 12c represents a trivalent linking group
  • X 1 represents S
  • *1 represents the bonding position with L 11 of formula (Ac-2)
  • *2 represents the bonding position of formula (Ac-2). It represents the bonding position of Ac-2) with P10 .
  • the trivalent linking group represented by L 12c is a hydrocarbon group; a hydrocarbon group and at least one kind selected from -O-, -CO-, -COO-, -OCO-, -NH- and -S-.
  • a hydrocarbon group is preferable.
  • P 10 represents a polymer chain.
  • the polymer chain represented by P 10 preferably has at least one structure selected from a polyester structure, a polyether structure, a polystyrene structure, and a poly(meth)acrylic structure.
  • the weight average molecular weight of the polymer chain P 10 is preferably 500 to 20,000.
  • the lower limit is preferably 1000 or more.
  • the upper limit is preferably 10,000 or less, more preferably 5,000 or less, and even more preferably 3,000 or less. If the weight average molecular weight of P 10 is within the above range, the pigment will have good dispersibility in the composition.
  • the resin having an aromatic carboxyl group is a resin having a repeating unit represented by formula (Ac-2), this resin is preferably used as a dispersant.
  • the polymer chain represented by P 10 may contain a crosslinkable group.
  • the crosslinkable group include ethylenically unsaturated bond-containing groups and cyclic ether groups.
  • At least one type of resin selected from graft polymers, star polymers, block copolymers, and resins in which at least one end of a polymer chain is capped with an acid group.
  • Such resins are preferably used as dispersants.
  • Examples of the graft polymer include a resin having a repeating unit having a graft chain and a resin having a repeating unit represented by the above-mentioned formula (Ac-2).
  • Examples of the graft chain include a graft chain containing at least one structure selected from a polyester structure, a polyether structure, a polystyrene structure, and a poly(meth)acrylic structure.
  • the terminal structure of the graft chain is not particularly limited. It may be a hydrogen atom or a substituent. Examples of the substituent include an alkyl group, an alkoxy group, an alkylthioether group, and the like.
  • alkyl groups or alkoxy groups having 5 to 30 carbon atoms are preferred.
  • the alkyl group and the alkoxy group may be linear, branched, or cyclic, and preferably linear or branched.
  • graft polymers include paragraph numbers 0025 to 0094 of JP2012-255128A, paragraphs 0022 to 0097 of JP2009-203462A, and paragraphs 0102 to 0166 of JP2012-255128A. Mention may be made of the resins mentioned.
  • star-shaped polymers include resins with a structure in which a plurality of polymer chains are bonded to a core portion.
  • Specific examples of star-shaped polymers include polymer compounds C-1 to C-31 described in paragraph numbers 0196 to 0209 of JP-A No. 2013-043962.
  • the block copolymers include a polymer block having a repeating unit containing an acid group or a basic group (hereinafter also referred to as block A), and a polymer block having a repeating unit not containing an acid group or a basic group. (hereinafter also referred to as block B) is preferably a block copolymer.
  • the block copolymers include block copolymers (B) described in paragraph numbers 0063 to 0112 of JP2014-219665A, and blocks described in paragraph numbers 0046 to 0076 of JP2018-156021A. Copolymers A1 can also be used, the contents of which are incorporated herein.
  • the resin in which at least one end of the polymer chain is capped with an acid group is a resin in which at least one end of the polymer chain contains at least one type of structure selected from a polyester structure, a polyether structure, and a poly(meth)acrylic structure.
  • examples include resins with a structure sealed with acid groups.
  • acid groups that block the ends of polymer chains include carboxy groups, sulfo groups, and phosphoric acid groups.
  • the dispersant include acidic dispersants (acidic resins) and basic dispersants (basic resins).
  • the acidic dispersant (acidic resin) refers to a resin in which the amount of acid groups is greater than the amount of basic groups.
  • the acidic dispersant (acidic resin) is preferably a resin in which the amount of acid groups is 70 mol % or more when the total amount of acid groups and basic groups is 100 mol %.
  • the acid group that the acidic dispersant (acidic resin) has is preferably a carboxy group.
  • the acid value of the acidic dispersant (acidic resin) is preferably 10 to 105 mgKOH/g.
  • the basic dispersant refers to a resin in which the amount of basic groups is greater 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 acid groups and basic groups is 100 mol%.
  • the basic group that the basic dispersant has is preferably an amino group.
  • Dispersants are also available as commercial products, and specific examples include the Disperbyk series manufactured by Byk Chemie (for example, Disperbyk-111, 161, 2001, etc.), Solsperse manufactured by Nippon Lubrizol Co., Ltd. series (for example, Solsperse 20000, 76500, etc.), Ajisper series manufactured by Ajinomoto Fine Techno Co., Ltd., A208F (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.), H-3606 (manufactured by Daiichi Kogyo Seiyaku Co., Ltd.), Sandet Examples include ET (manufactured by Sanyo Chemical Industries, Ltd.). Further, the product described in paragraph number 0129 of JP 2012-137564A and the product described in paragraph number 0235 of JP 2017-194662A can also be used as a dispersant.
  • Disperbyk series manufactured by Byk Chemie for example, Disperbyk-111, 161, 2001, etc.
  • the content of the resin in the total solid content of the resin composition is preferably 1 to 80% by mass.
  • the lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, and particularly preferably 20% by mass or more.
  • the upper limit is preferably 60% by mass or less, more preferably 50% by mass or less.
  • the content of the resin having acid groups in the total solid content of the resin composition is preferably 1 to 80% by mass.
  • the lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 15% by mass or more, and particularly preferably 20% by mass or more.
  • the upper limit is preferably 60% by mass or less, more preferably 50% by mass or less.
  • the content of the resin as a dispersant is preferably 10 to 150 parts by weight per 100 parts by weight of the pigment.
  • the lower limit is preferably 15 parts by mass or more, more preferably 20 parts by mass or more.
  • the upper limit is preferably 100 parts by mass or less, more preferably 80 parts by mass or less.
  • the resin composition of the present invention contains a solvent.
  • the solvent include organic solvents.
  • the type of solvent is basically not particularly limited as long as it satisfies the solubility of each component and the coatability of the composition.
  • the organic solvent include ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, and hydrocarbon solvents.
  • paragraph number 0223 of International Publication No. 2015/166779 can be referred to, the contents of which are incorporated herein.
  • Ester solvents substituted with a cyclic alkyl group and ketone solvents substituted with a cyclic alkyl group can also be preferably used.
  • organic solvents 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, 3-pentanone, 4-heptanone, cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, cycloheptanone, cyclooctanone, cyclohexyl acetate, cyclopentanone, ethyl carbitol acetate, butyl carbyl Tall acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N,N-di
  • aromatic hydrocarbons benzene, toluene, xylene, ethylbenzene, etc.
  • organic solvents for environmental reasons (for example, 50 mass ppm (parts) based on the total amount of organic solvents). per million), 10 mass ppm or less, and 1 mass ppm or less).
  • an organic solvent with a low metal content it is preferable to use an organic solvent with a low metal content, and it is preferable that the metal content of the organic solvent is, for example, 10 mass ppb (parts per billion) or less. If necessary, an organic solvent at a mass ppt (parts per trillion) level may be used, and such an organic solvent is provided by Toyo Gosei Co., Ltd. (Kagaku Kogyo Nippo, November 13, 2015). .
  • Examples of methods for removing impurities such as metals from organic solvents 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 material of the filter is preferably polytetrafluoroethylene, polyethylene, or nylon.
  • the organic solvent may contain isomers (compounds with the same number of atoms but different structures). Moreover, only one type of isomer may be included, or multiple types may be included.
  • the content of peroxide in the organic solvent is 0.8 mmol/L or less, and it is more preferable that the organic solvent contains substantially no peroxide.
  • the content of the solvent in the resin composition is preferably 10 to 95% by mass, more preferably 20 to 90% by mass, and even more preferably 30 to 90% by mass.
  • the resin composition of the present invention does not substantially contain environmentally regulated substances.
  • "not substantially containing environmentally controlled substances” means that the content of environmentally controlled substances in the resin composition is 50 mass ppm or less, preferably 30 mass ppm or less. , more preferably 10 mass ppm or less, particularly preferably 1 mass ppm or less.
  • environmentally controlled substances include benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene.
  • REACH Registration Evaluation Authorization and Restriction of CHemicals
  • PRTR Policy Release and It is registered as an environmentally regulated substance under the Transfer Register Act
  • VOC Volatile Organic Compounds
  • VOC Volatile Organic Compounds
  • methods for reducing environmentally controlled substances include a method of heating or reducing pressure in the system to raise the temperature above the boiling point of the environmentally controlled substance to distill off the environmentally controlled substances from the system.
  • distillation methods can be used at the stage of raw materials, at the stage of products obtained by reacting raw materials (for example, resin solution or polyfunctional monomer solution after polymerization), or at the stage of resin compositions prepared by mixing these compounds. This is possible at any stage.
  • the resin composition of the present invention contains a polymerizable compound.
  • the polymerizable compound include compounds having an ethylenically unsaturated bond-containing group.
  • the ethylenically unsaturated bond-containing group include a vinyl group, a (meth)allyl group, a (meth)acryloyl group, and the like.
  • the polymerizable compound is preferably a radically polymerizable compound.
  • the polymerizable compound may be in any chemical form such as a monomer, prepolymer, or oligomer, but monomers are preferred.
  • the molecular weight of the polymerizable compound is preferably 100 to 2,500.
  • the upper limit is preferably 2000 or less, more preferably 1500 or less.
  • the lower limit is preferably 150 or more, more preferably 250 or more.
  • the polymerizable compound is preferably a compound containing three or more ethylenically unsaturated bond-containing groups, and more preferably a compound containing four or more ethylenically unsaturated bond-containing groups.
  • the upper limit of the ethylenically unsaturated bond-containing groups is preferably 15 or less, more preferably 10 or less, and even more preferably 6 or less from the viewpoint of storage stability of the resin composition.
  • the polymerizable compound is preferably a trifunctional or more functional (meth)acrylate compound, more preferably a 3-15 functional (meth)acrylate compound, and a 3-10 functional (meth)acrylate compound. are more preferred, and tri- to hexa-functional (meth)acrylate compounds are particularly preferred.
  • polymerizable compounds include paragraph numbers 0095 to 0108 of JP 2009-288705, paragraph 0227 of JP 2013-029760, paragraph 0254 to 0257 of JP 2008-292970, and The compounds described in paragraph numbers 0034 to 0038 of JP 2013-253224, paragraph 0477 of JP 2012-208494, JP 2017-048367, JP 6057891, and JP 6031807 are , the contents of which are incorporated herein.
  • polymerizable compounds examples include dipentaerythritol tri(meth)acrylate (commercially available product: KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetra(meth)acrylate (commercially available product: KAYARAD D-320) ; made by Nippon Kayaku Co., Ltd.), dipentaerythritol penta(meth)acrylate (as a commercial product KAYARAD D-310; made by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa(meth)acrylate (as a commercial product KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd., NK ester A-DPH-12E; manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), diglycerin EO (ethylene oxide) modified (meth)acrylate (commercially available: M-460; Toa) Synthetic), pentaery
  • Polymerizable compounds include trimethylolpropane tri(meth)acrylate, trimethylolpropane propylene oxide modified tri(meth)acrylate, trimethylolpropane ethylene oxide modified tri(meth)acrylate, isocyanuric acid ethylene oxide modified tri(meth)acrylate, and pentaerythritol.
  • Trifunctional (meth)acrylate compounds such as tri(meth)acrylate can also be used.
  • Commercially available trifunctional (meth)acrylate compounds include Aronix M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306, M-305.
  • M-303, M-452, M-450 (manufactured by Toagosei Co., Ltd.), NK ester A9300, A-GLY-9E, A-GLY-20E, A-TMM-3, A-TMM-3L, A -TMM-3LM-N, A-TMPT, TMPT (manufactured by Shin Nakamura Chemical Co., Ltd.), KAYARAD GPO-303, TMPTA, THE-330, TPA-330, PET-30 (manufactured by Nippon Kayaku Co., Ltd.) Examples include.
  • a compound having an acid group such as a carboxy group, a sulfo group, or a phosphoric acid group can also be used.
  • Commercially available products of such compounds include Aronix M-305, M-510, M-520, Aronix TO-2349 (manufactured by Toagosei Co., Ltd.), and the like.
  • a compound having a caprolactone structure can also be used.
  • the description in paragraphs 0042 to 0045 of JP-A No. 2013-253224 can be referred to, the contents of which are incorporated herein.
  • Examples of compounds having a caprolactone structure include DPCA-20, DPCA-30, DPCA-60, and DPCA-120, which are commercially available from Nippon Kayaku Co., Ltd. as the KAYARAD DPCA series.
  • a polymerizable compound having an alkyleneoxy group can also be used.
  • the polymerizable compound having an alkyleneoxy group is preferably a polymerizable compound having an ethyleneoxy group and/or a propyleneoxy group, more preferably a polymerizable compound having an ethyleneoxy group, and a polymerizable compound having 4 to 20 ethyleneoxy groups. More preferred are hexafunctional (meth)acrylate compounds.
  • Commercially available polymerizable compounds having an alkyleneoxy group include, for example, SR-494, a tetrafunctional (meth)acrylate having four ethyleneoxy groups manufactured by Sartomer Co., Ltd., and isobutyleneoxy group manufactured by Nippon Kayaku Co., Ltd. Examples include KAYARAD TPA-330, which is a trifunctional (meth)acrylate having three.
  • a polymerizable compound having a fluorene skeleton can also be used.
  • Commercially available products include Ogsol EA-0200 and EA-0300 (manufactured by Osaka Gas Chemical Co., Ltd., (meth)acrylate monomer having a fluorene skeleton).
  • the polymerizable compound it is also preferable to use a compound that does not substantially contain environmentally controlled substances such as toluene.
  • environmentally controlled substances such as toluene.
  • Commercially available products of such compounds include KAYARAD DPHA LT, KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.), and the like.
  • Examples of the polymerizable compound include urethane acrylates as described in Japanese Patent Publication No. 48-041708, Japanese Patent Application Laid-Open No. 51-037193, Japanese Patent Publication No. 02-032293, and Japanese Patent Publication No. 02-016765; Urethane compounds having an ethylene oxide skeleton described in Japanese Patent Publication No. 58-049860, Japanese Patent Publication No. 56-017654, Japanese Patent Publication No. 62-039417, and Japanese Patent Publication No. 62-039418 are also suitable.
  • polymerizable compounds having an amino structure or a sulfide structure in the molecule described in JP-A-63-277653, JP-A-63-260909, and JP-A-01-105238.
  • the polymerizable compounds include UA-7200 (manufactured by Shin Nakamura Chemical Industry Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, Commercially available products such as T-600, AI-600, LINC-202UA (manufactured by Kyoeisha Chemical Co., Ltd.) can also be used.
  • the content of the polymerizable compound in the total solid content of the resin composition is preferably 1 to 35% by mass.
  • the upper limit is preferably 30% by mass or less, more preferably 25% by mass or less, even more preferably 20% by mass or less, and particularly preferably 10% by mass or less.
  • the lower limit is preferably 2% by mass or more, more preferably 5% by mass or more.
  • the resin composition of the present invention may contain only one kind of polymerizable compound, or may contain two or more kinds of polymerizable compounds. When two or more types of polymerizable compounds are included, it is preferable that the total amount thereof falls within the above range.
  • the resin composition of the present invention preferably contains a photopolymerization initiator.
  • the photopolymerization initiator is not particularly limited and can be appropriately selected from known photopolymerization initiators. For example, compounds having photosensitivity to light in the ultraviolet to visible range are preferred.
  • the photopolymerization initiator is preferably a radical photopolymerization initiator.
  • photopolymerization initiators include halogenated hydrocarbon derivatives (e.g., compounds with a triazine skeleton, compounds with an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, and the like.
  • halogenated hydrocarbon derivatives e.g., compounds with a triazine skeleton, compounds with an oxadiazole skeleton, etc.
  • acylphosphine compounds e.g., acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, and the like.
  • photopolymerization initiators include trihalomethyltriazine compounds, benzyl dimethyl ketal compounds, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, acylphosphine compounds, phosphine oxide compounds, metallocene compounds, oxime compounds, and hexaarylbylene compounds.
  • imidazole compounds onium compounds, benzothiazole compounds, benzophenone compounds, acetophenone compounds, cyclopentadiene-benzene-iron complexes, halomethyloxadiazole compounds and 3-aryl substituted coumarin compounds, oxime compounds, ⁇ -hydroxyketones
  • the compound is more preferably a compound selected from a compound, an ⁇ -aminoketone compound, and an acylphosphine compound, and even more preferably an oxime compound.
  • photopolymerization initiators compounds described in paragraphs 0065 to 0111 of JP-A-2014-130173, compounds described in Japanese Patent No. 6301489, MATERIAL STAGE 37 to 60p, vol. 19, No.
  • hexaarylbiimidazole compounds include 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1'-biimidazole, etc. can be mentioned.
  • ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (manufactured by IGM Resins B.V.), Irgacure 184, and Irgacure 117. 3, Irgacure 2959, Irgacure 127 (all BASF (manufactured by a company).
  • Commercially available ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (manufactured by IGM Resins B.V.), Irgacure 907, and Irgacure 36.
  • Irgacure 369E Irgacure 379EG (all manufactured by BASF) (manufactured by).
  • Commercially available acylphosphine compounds include Omnirad 819, Omnirad TPO (manufactured by IGM Resins B.V.), Irgacure 819, Irgacure TPO (manufactured by BASF), and the like.
  • Examples of oxime compounds include the compound described in paragraph number 0142 of International Publication No. 2022/085485, the compound described in Patent No. 5430746, the compound described in Patent No. 5647738, and the general formula ( Examples include the compound represented by 1), the compound described in paragraphs 0022 to 0024, the compound represented by general formula (1) and the compound described in paragraphs 0117 to 0120 of JP-A-2021-170089.
  • oxime compounds include 3-benzoyloxyiminobutan-2-one, 3-acetoxyiminobutan-2-one, 3-propionyloxyiminobutan-2-one, 2-acetoxyiminopentan-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, 2-ethoxycarbonyloxyimino -1-phenylpropan-1-one, 1-[4-(phenylthio)phenyl]-3-cyclohexyl-propane-1,2-dione-2-(O-acetyloxime), and the like.
  • photopolymerization initiators include oxime compounds having a fluorene ring, oxime compounds having a skeleton in which at least one benzene ring of a carbazole ring is a naphthalene ring, oxime compounds having a fluorine atom, oxime compounds having a nitro group, and benzofuran skeleton.
  • An oxime compound having a carbazole skeleton bonded with a substituent having a hydroxy group, and compounds described in paragraphs 0143 to 0149 of International Publication No. 2022/085485 can also be used.
  • oxime compounds preferably used in the present invention are shown below, but the present invention is not limited thereto.
  • the oxime compound is preferably a compound having a maximum absorption wavelength in a wavelength range of 350 to 500 nm, more preferably a compound having a maximum absorption wavelength in a wavelength range of 360 to 480 nm.
  • the molar extinction coefficient of the oxime compound at a wavelength of 365 nm or 405 nm is preferably high, more preferably from 1000 to 300,000, even more preferably from 2000 to 300,000, and even more preferably from 5000 to 200,000. It is particularly preferable that there be.
  • the molar extinction coefficient of a compound can be measured using a known method. For example, it is preferable to measure with a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian) using an ethyl acetate solvent at a concentration of 0.01 g/L.
  • the photopolymerization initiator it is also preferable to use a combination of Irgacure OXE01 (manufactured by BASF) and/or Irgacure OXE02 (manufactured by BASF) and Omnirad 2959 (manufactured by IGM Resins B.V.).
  • a difunctional, trifunctional or more functional photoradical polymerization initiator may be used as the photopolymerization initiator.
  • a radical photopolymerization initiator two or more radicals are generated from one molecule of the radical photopolymerization initiator, so that good sensitivity can be obtained.
  • the crystallinity decreases and the solubility in solvents improves, making it difficult to precipitate over time, thereby improving the stability of the resin composition over time.
  • Specific examples of bifunctional or trifunctional or more functional photoradical polymerization initiators include those listed in Japanese Patent Publication No. 2010-527339, Japanese Patent Publication No. 2011-524436, International Publication No.
  • the content of the photopolymerization initiator in the total solid content of the resin composition is preferably 0.1 to 30% by mass.
  • the lower limit is preferably 0.5% by mass or more, more preferably 1% by mass or more.
  • the upper limit is preferably 20% by mass or less, more preferably 15% by mass or less.
  • the resin composition of the present invention may contain only one type of photopolymerization initiator, or may contain two or more types of photopolymerization initiators. When two or more types of photopolymerization initiators are included, the total amount thereof is preferably within the above range.
  • the resin composition of the present invention can 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 (hereinafter also referred to as an epoxy compound).
  • the epoxy compound include compounds having one or more epoxy groups in one molecule, and preferably compounds having two or more epoxy groups.
  • the epoxy compound is preferably a compound having 1 to 100 epoxy groups in one molecule.
  • the upper limit of the epoxy groups contained in the epoxy compound can be, for example, 10 or less, or 5 or less.
  • the lower limit of the epoxy groups contained in the epoxy compound is preferably two or more.
  • epoxy compounds include those described in paragraph numbers 0034 to 0036 of JP2013-011869, paragraphs 0147 to 0156 of JP2014-043556, and paragraphs 0085 to 0092 of JP2014-089408.
  • Compounds, compounds described in JP 2017-179172, xanthene type epoxy resins described in JP 2021-195421, and xanthene epoxy resins described in JP 2021-195422 can also be used.
  • the epoxy compound may be a low-molecular compound (for example, molecular weight less than 2000, or even less than 1000), or a macromolecule (for example, molecular weight 1000 or more; in the case of a polymer, the weight average molecular weight is 1000 or more). But that's fine.
  • 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 even more preferably 3,000 or less.
  • EHPE3150 manufactured by Daicel Corporation
  • EPICLON N-695 manufactured by DIC Corporation
  • Marproof G-0150M G-0105SA, G-0130SP, and G-0130SP.
  • -0250SP G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, G-01758 (all of which are epoxy group-containing polymers manufactured by NOF Corporation).
  • the content of the compound having a cyclic ether group in the total solid content of the resin composition is preferably 0.1 to 20% by mass.
  • the lower limit is, for example, more preferably 0.5% by mass or more, and even more preferably 1% by mass or more.
  • the upper limit is, for example, more preferably 15% by mass or less, and even more preferably 10% by mass or less. Only one kind of compound having a cyclic ether group may be used, or two or more kinds thereof may be used. When two or more types are used, it is preferable that their total amount falls within the above range.
  • the resin composition of the present invention can contain a curing accelerator.
  • the curing accelerator include thiol compounds, methylol compounds, amine compounds, phosphonium salt compounds, amidine salt compounds, amide compounds, base generators, isocyanate compounds, alkoxysilane compounds, onium salt compounds, and the like.
  • Specific examples of the curing accelerator include the compound described in paragraph 0164 of International Publication No. 2022/085485, the compound described in JP 2021-181406, and the like.
  • the content of the curing accelerator in the total solid content of the resin composition is preferably 0.3 to 8.9% by mass, more preferably 0.8 to 6.4% by mass.
  • the resin composition of the present invention can contain an ultraviolet absorber.
  • the ultraviolet absorber include conjugated diene compounds, aminodiene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indole compounds, triazine compounds, dibenzoyl compounds, and the like.
  • Specific examples of ultraviolet absorbers include the compounds described in paragraph number 0179 of International Publication No. 2022/085485, the reactive triazine ultraviolet absorbers described in JP-A No. 2021-178918, and the compounds described in JP-A No. 2022-007884. It is also possible to use the ultraviolet absorbers described.
  • the content of the ultraviolet absorber in the total solid content of the resin composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass.
  • the resin composition of the present invention may contain only one type of ultraviolet absorber, or may contain two or more types of ultraviolet absorbers. When two or more types of ultraviolet absorbers are included, the total amount thereof is preferably within the above range.
  • the resin composition of the present invention can contain a polymerization inhibitor.
  • Polymerization inhibitors include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis(3-methyl-6-tert-butylphenol), Examples include 2,2'-methylenebis(4-methyl-6-t-butylphenol) and N-nitrosophenylhydroxyamine salts (ammonium salts, cerous salts, etc.). Among them, p-methoxyphenol is preferred.
  • the content of the polymerization inhibitor in the total solid content of the resin composition is preferably 0.0001 to 5% by mass.
  • the resin composition of the present invention may contain only one kind of polymerization inhibitor, or may contain two or more kinds of polymerization inhibitors. When two or more types of polymerization inhibitors are included, the total amount thereof is preferably within the above range.
  • the resin composition of the present invention can contain a silane coupling agent.
  • a silane coupling agent means a silane compound having a hydrolyzable group and other functional groups.
  • hydrolyzable group refers to a substituent that is directly bonded to a silicon atom and can form a siloxane bond through 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 an alkoxy group is preferred. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group.
  • Examples of functional groups other than hydrolyzable groups include vinyl groups, (meth)allyl groups, (meth)acryloyl groups, mercapto groups, epoxy groups, oxetanyl groups, amino groups, ureido groups, sulfide groups, and isocyanate groups. , phenyl group, etc., and amino group, (meth)acryloyl group and epoxy group are preferable.
  • Specific examples of the silane coupling agent include compounds described in paragraph 0177 of International Publication No. 2022/085485.
  • the content of the silane coupling agent in the total solid content of the resin composition is preferably 0.01 to 15% by mass, more preferably 0.05 to 10% by mass.
  • the resin composition of the present invention may contain only one type of silane coupling agent, or may contain two or more types of silane coupling agents. When two or more types of silane coupling agents are included, the total amount thereof is preferably within the above range.
  • the resin composition of the present invention can contain a surfactant.
  • a surfactant various surfactants such as fluorine surfactants, nonionic surfactants, cationic surfactants, anionic surfactants, and silicone surfactants can be used.
  • the surfactant is preferably a silicone surfactant or a fluorine surfactant.
  • fluorosurfactant compounds described in paragraph numbers 0167 to 0173 of International Publication No. 2022/085485 can be used.
  • nonionic surfactants examples include compounds described in paragraph 0174 of International Publication No. 2022/085485.
  • silicone surfactants examples include DOWSIL SH8400, SH8400 FLUID, FZ-2122, 67 Additive, 74 Additive, M Additive, SF 8419 OIL (manufactured by Dow Toray Industries, Inc.), and TSF- 4300, TSF-4445, TSF-4460, TSF-4452 (manufactured by Momentive Performance Materials), KP-341, KF-6000, KF-6001, KF-6002, KF-6003 (manufactured by Shin-Etsu Chemical Co., Ltd.) , BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-3760, BYK-UV3510 (manufactured by BYK Chemie), and the like.
  • a compound having the following structure can also be used as the silicone surfactant.
  • the content of the surfactant in the total solid content of the resin composition is preferably 0.001% by mass to 5.0% by mass, more preferably 0.005% to 3.0% by mass.
  • the resin composition of the present invention may contain only one type of surfactant, or may contain two or more types of surfactant. When two or more types of surfactants are included, the total amount thereof is preferably within the above range.
  • the resin composition of the present invention can contain an antioxidant.
  • the antioxidant include phenolic antioxidants, amine antioxidants, phosphorus antioxidants, sulfur antioxidants, and the like.
  • phenolic antioxidants include hindered phenol compounds.
  • the phenolic antioxidant is preferably a compound having a substituent at a site adjacent to the phenolic hydroxy group (ortho position).
  • the above-mentioned substituents are preferably substituted or unsubstituted alkyl groups having 1 to 22 carbon atoms.
  • a compound having a phenol group and a phosphorous acid ester group in the same molecule is also preferable.
  • phosphorus-based antioxidants can also be suitably used.
  • 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 (manufactured by ADEKA Co., Ltd.).
  • antioxidants include compounds described in paragraph numbers 0023 to 0048 of Patent No. 6268967, compounds described in International Publication No. 2017/006600, compounds described in International Publication No. 2017/164024, Compounds described in Korean Patent Publication No. 10-2019-0059371 can also be used.
  • the content of the antioxidant in the total solid content of the resin composition is preferably 0.01 to 20% by mass, more preferably 0.3 to 15% by mass.
  • the resin composition of the present invention may contain only one type of antioxidant, or may contain two or more types of antioxidant. When two or more types of antioxidants are included, the total amount thereof is preferably within the above range.
  • the resin composition of the present invention may contain sensitizers, curing accelerators, fillers, thermosetting accelerators, plasticizers, and other auxiliary agents (for example, conductive particles, antifoaming agents, flame retardants, (leveling agents, peeling accelerators, fragrances, surface tension modifiers, chain transfer agents, etc.) may also be included.
  • sensitizers for example, curing accelerators, fillers, thermosetting accelerators, plasticizers, and other auxiliary agents
  • auxiliary agents for example, conductive particles, antifoaming agents, flame retardants, (leveling agents, peeling accelerators, fragrances, surface tension modifiers, chain transfer agents, etc.
  • the resin composition of the present invention may also contain a light resistance improver.
  • Examples of the light resistance improver include compounds described in paragraph 0183 of International Publication No. 2022/085485.
  • the resin composition of the present invention does not substantially contain terephthalic acid ester.
  • substantially not containing means that the content of terephthalic acid ester is 1000 mass ppb or less in the total amount of the resin composition, more preferably 100 mass ppb or less, Particularly preferred is zero.
  • the resin composition of the present invention preferably has a free metal content of 100 ppm or less, more preferably 50 ppm or less. Further, the free halogen content is preferably 100 ppm or less, more preferably 50 ppm or less. Examples of methods for reducing free metals and halogens in the resin composition include washing with ion-exchanged water, filtration, ultrafiltration, and purification using ion-exchange resins.
  • perfluoroalkyl sulfonic acids and their salts may be regulated.
  • perfluoroalkylsulfonic acids particularly perfluoroalkylsulfonic acids whose perfluoroalkyl group has 6 to 8 carbon atoms
  • salts thereof and perfluoroalkylsulfonic acids
  • the content of fluoroalkylcarboxylic acid (particularly perfluoroalkylcarboxylic acid whose perfluoroalkyl group has 6 to 8 carbon atoms) and its salt is 0.01 ppb to 1,000 ppb based on the total solid content of the resin composition.
  • the resin composition of the present invention may be substantially free of perfluoroalkylsulfonic acid and its salt, and perfluoroalkylcarboxylic acid and its salt.
  • a compound that can be substituted for perfluoroalkylsulfonic acid and its salt and a compound that can be substituted for perfluoroalkylcarboxylic acid and its salt, perfluoroalkylsulfonic acid and its salt, and perfluoroalkylcarboxylic acid
  • Compounds that can be substituted for regulated compounds include, for example, compounds that are excluded from regulated targets due to differences in the number of carbon atoms in perfluoroalkyl groups.
  • the resin composition of the present invention may contain perfluoroalkyl sulfonic acids and salts thereof, and perfluoroalkyl carboxylic acids and salts thereof within the maximum allowable range.
  • the container for storing the resin composition is not particularly limited, and any known container can be used. Further, as the storage container, the container described in paragraph number 0187 of International Publication No. 2022/085485 can be used.
  • the method for producing a resin composition of the present invention is characterized by comprising a step of dispersing a pigment, a pigment derivative having a BET specific surface area of 2 to 300 m 2 /g by nitrogen adsorption method, and a resin in a solvent. do.
  • the solvent, pigment, and resin examples include the solvents, pigments, and resins described above as being included in the resin composition.
  • the resin includes a resin as a dispersant.
  • the preferable chemical structure of the pigment derivative is the same as that explained in the section of the specific particles contained in the resin composition mentioned above.
  • the BET specific surface area of the pigment derivative determined by the nitrogen adsorption method is 2 to 300 m 2 /g.
  • the lower limit of the BET specific surface area of the pigment derivative is preferably 3 m 2 /g or more, more preferably 5 m 2 /g or more.
  • the upper limit of the BET specific surface area of the pigment derivative is preferably 250 m 2 /g or less, more preferably 200 m 2 /g or less, even more preferably 150 m 2 /g or less, and 100 m 2 /g or less. It is even more preferable that If the BET specific surface area of the pigment derivative measured by the nitrogen adsorption method is within the above range, a resin composition with excellent pigment dispersion stability can be produced.
  • the average primary particle diameter of the pigment derivative is preferably 5 to 200 nm.
  • the upper limit is preferably 150 nm or less, more preferably 100 nm or less.
  • the lower limit is preferably 10 nm or more, more preferably 20 nm or more.
  • the average primary particle diameter of the pigment is preferably 1 to 200 nm.
  • the lower limit is preferably 5 nm or more, more preferably 10 nm or more, even more preferably 20 nm or more, and even more preferably 30 nm or more.
  • the upper limit is preferably 180 nm or less, more preferably 150 nm or less, even more preferably 100 nm or less, even more preferably 90 nm or less, and particularly preferably 80 nm or less.
  • the difference between the average primary particle diameter of the pigment derivative and the average primary particle diameter of the pigment is preferably 0 to 100 nm.
  • the upper limit is preferably 50 nm or less, more preferably 30 nm or less.
  • the lower limit is preferably 2 nm or more, more preferably 5 nm or more.
  • the method for producing the resin composition of the present invention includes dispersion in the above step (step of dispersing the pigment, a pigment derivative having a BET specific surface area of 2 to 300 m 2 /g by nitrogen adsorption method, and the resin in a solvent).
  • the method may further include a step of mixing the obtained dispersion with other materials such as a polymerizable compound, a photopolymerization initiator, a resin, and a solvent.
  • Other materials can be selected as appropriate depending on the use of the resin composition. For example, when manufacturing a resin composition for photolithography, it is preferable to select a material containing a polymerizable compound and a photopolymerization initiator as other materials.
  • the materials described in the section of the resin composition described above such as resins, solvents, surfactants, silane coupling agents, polymerization inhibitors, and ultraviolet absorbers, may be added.
  • the resin composition it is preferable to filter the resin composition with a filter for the purpose of removing foreign substances and reducing defects.
  • a filter for the purpose of removing foreign substances and reducing defects.
  • Examples of the type of filter and filtration method used for filtration include the filters and filtration methods described in paragraph numbers 0196 to 0199 of International Publication No. 2022/085485.
  • the pigment derivative of the present invention is a particle of a compound having at least one structure selected from the group consisting of a pigment structure and a triazine structure and an acid group or a basic group, and the above particles are nitrogen-adsorbing particles. It is characterized by a BET specific surface area of 2 to 300 m 2 /g.
  • the lower limit of the BET specific surface area of the pigment derivative is preferably 3 m 2 /g or more, more preferably 5 m 2 /g or more.
  • the upper limit of the BET specific surface area of the pigment derivative is preferably 250 m 2 /g or less, more preferably 200 m 2 /g or less, even more preferably 150 m 2 /g or less, and 100 m 2 /g or less. It is even more preferable that
  • the average primary particle diameter of the pigment derivative is preferably 5 to 200 nm.
  • the upper limit is preferably 150 nm or less, more preferably 100 nm or less.
  • the lower limit is preferably 10 nm or more, more preferably 20 nm or more.
  • Preferred embodiments of the chemical structure of the pigment derivative are the same as those explained in the section regarding the specific particles contained in the resin composition described above.
  • the pigment derivative of the present invention is preferably a dispersion aid.
  • the membrane of the present invention is a membrane obtained from the resin composition of the present invention described above.
  • the film thickness of the film of the present invention can be adjusted as appropriate depending on 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 even more preferably 0.3 ⁇ m or more.
  • the film of the present invention can be used for color filters, near-infrared transmission filters, near-infrared cut filters, black matrices, light-shielding films, and the like.
  • the film of the present invention can be preferably used as a colored pixel of a color filter. Examples of colored pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, and yellow pixels.
  • the maximum absorption wavelength of the film of the present invention is preferably in the wavelength range of 700 to 1800 nm, more preferably in the wavelength range of 700 to 1400 nm, More preferably, the wavelength range is from 700 to 1200 nm.
  • the transmittance of the film over the entire wavelength range of 400 to 650 nm is preferably 70% or more, more preferably 80% or more, and even more preferably 90% or more.
  • the transmittance of the film at at least one point in the wavelength range of 700 to 1800 nm is preferably 20% or less.
  • the ratio of absorbance Amax at the maximum absorption wavelength to absorbance A550 at a wavelength of 550 nm is preferably 20 to 500, more preferably 50 to 500, and 70 to 450. It is more preferably 100 to 400, particularly preferably 100 to 400.
  • the film of the present invention preferably has any of the following spectral properties (i1) to (i5).
  • a film having such spectral characteristics can block light in a wavelength range of 400 to 640 nm and transmit light with a wavelength exceeding 750 nm.
  • the maximum value of transmittance in the wavelength range of 400 to 750 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of transmittance in the wavelength range of 900 to 1500 nm is 70% or more (preferably 75% or more, more preferably 80% or more).
  • a film having such spectral characteristics can block light in the wavelength range of 400 to 750 nm and transmit light with a wavelength exceeding 850 nm.
  • the maximum value of transmittance in the wavelength range of 400 to 830 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of transmittance in the wavelength range of 1000 to 1500 nm is 70% or more (preferably 75% or more, more preferably 80% or more).
  • a film having such spectral characteristics can block light in the wavelength range of 400 to 830 nm and transmit light with a wavelength exceeding 950 nm.
  • the maximum value of transmittance in the wavelength range of 400 to 950 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of transmittance in the wavelength range of 1100 to 1500 nm is 70% or more (preferably 75% or more, more preferably 80% or more).
  • a film having such spectral characteristics can block light in a wavelength range of 400 to 950 nm and transmit light with a wavelength exceeding 1050 nm.
  • the maximum value of transmittance in the wavelength range of 400 to 1050 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum value of transmittance in the wavelength range of 1200 to 1500 nm is 70% or more (preferably 75% or more, more preferably 80% or more).
  • a film having such spectral characteristics can block light in the wavelength range of 400 to 1050 nm and transmit light with a wavelength exceeding 1150 nm.
  • the film of the present invention can be manufactured through a step of applying the resin composition of the present invention.
  • the film manufacturing method preferably further includes a step of forming a pattern (pixel). Examples of methods for forming patterns (pixels) include photolithography and dry etching, with photolithography being preferred.
  • Pattern formation by the photolithography method includes a step of forming a resin composition layer on a support using the resin composition of the present invention, a step of exposing the resin composition layer to light in a pattern, and a step of exposing the resin composition layer to light. It is preferable to include a step of developing and removing the exposed portion to form a pattern (pixel). If necessary, a step of baking the resin composition layer (pre-bake step) and a step of baking the developed pattern (pixel) (post-bake step) may be provided.
  • a resin composition layer is formed on a support using the resin composition of the present invention.
  • the support is not particularly limited and can be appropriately selected depending on the application.
  • a glass substrate, a silicon substrate, etc. may be mentioned, and a silicon substrate is preferable.
  • a charge coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, etc. may be formed on the silicon substrate.
  • CMOS complementary metal oxide semiconductor
  • a black matrix that isolates each pixel may be formed on the silicon substrate.
  • the silicon substrate may be provided with a base layer for improving adhesion with the upper layer, preventing substance diffusion, or flattening the substrate surface.
  • the surface contact angle of the underlayer is preferably 20 to 70° when measured with diiodomethane. Further, it is preferable that the angle is 30 to 80° when measured with water.
  • a known method can be used.
  • the coating method described in paragraph number 0207 of International Publication No. 2022/085485 can be used.
  • the resin composition layer formed on the support may be dried (prebaked). If the film is manufactured by a low-temperature process, prebaking may not be performed.
  • 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 prebake time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, even more preferably 80 to 220 seconds. Prebaking can be performed on a hot plate, oven, or the like.
  • the resin composition layer is exposed in a pattern (exposure step).
  • the resin composition layer can be exposed in a pattern by exposing the resin composition layer to light through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. This allows the exposed portion to be cured.
  • Radiation (light) that can be used during exposure includes g-line, i-line, etc. Furthermore, light with a wavelength of 300 nm or less (preferably light with a wavelength of 180 to 300 nm) can also be used. Examples of light with a wavelength of 300 nm or less include KrF rays (wavelength 248 nm), ArF rays (wavelength 193 nm), and KrF rays (wavelength 248 nm). Furthermore, a long-wave light source of 300 nm or more can also be used. As a light source, an electrodeless ultraviolet lamp system, a hybrid ultraviolet and infrared curing can be used.
  • pulse exposure is an exposure method in which exposure is performed by repeating light irradiation and pauses in short cycles (for example, on the millisecond level or less).
  • the irradiation amount is, for example, preferably 0.03 to 2.5 J/cm 2 , more preferably 0.05 to 1.0 J/cm 2 .
  • the oxygen concentration during exposure can be appropriately selected, and in addition to being carried out in the atmosphere, for example, in a low oxygen atmosphere with an oxygen concentration of 19% by volume or less (for example, 15% by volume, 5% by volume, or substantially
  • the exposure may be performed in an oxygen-free atmosphere (without oxygen), or in a high oxygen atmosphere where the oxygen concentration exceeds 21 volume % (for example, 22 volume %, 30 volume %, or 50 volume %).
  • the exposure illuminance can be set as appropriate, and is usually selected from the range of 1000W/m 2 to 100000W/m 2 (for example, 5000W/m 2 , 15000W/m 2 , or 35000W/m 2 ). I can do it.
  • the oxygen concentration and the exposure illuminance may be appropriately combined.
  • the illuminance may be 10,000 W/m 2 when the oxygen concentration is 10% by volume, and 20,000 W/m 2 when the oxygen concentration is 35% by volume.
  • the unexposed areas of the resin composition layer are developed and removed to form a pattern (pixel).
  • the unexposed areas of the resin composition layer can be removed by development using a developer.
  • the unexposed portions of the resin composition layer in the exposure step are eluted into the developer, leaving only the photocured portions.
  • the temperature of the developer is preferably, for example, 20 to 30°C.
  • the development time is preferably 20 to 180 seconds. Furthermore, in order to improve the ability to remove residues, the process of shaking off the developer every 60 seconds and supplying a new developer may be repeated several times.
  • Examples of the developer include organic solvents, alkaline developers, and alkaline developers are preferably used.
  • the developer and cleaning method after development the developer and cleaning method described in paragraph number 0214 of International Publication No. 2022/085485 can be used.
  • Additional exposure processing and post-bake are post-development curing processing to complete curing.
  • the heating temperature in post-baking is, for example, preferably 100 to 240°C, more preferably 200 to 240°C.
  • Post-baking can be carried out in a continuous or batch manner using a heating means such as a hot plate, convection oven (hot air circulation dryer), or high-frequency heater to maintain the developed film under the above conditions.
  • the light used for exposure is preferably light with 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.
  • Pattern formation by the dry etching method includes the steps of forming a resin composition layer on a support using the resin composition of the present invention, and curing the entire resin composition layer to form a cured product layer; A step of forming a photoresist layer on this cured material layer, a step of exposing the photoresist layer in a pattern and then developing it to form a resist pattern, and etching the cured material layer using this resist pattern as a mask. It is preferable to include a step of dry etching using gas. In forming the photoresist layer, it is preferable to further perform a prebaking process.
  • the optical filter of the present invention has the film of the present invention described above.
  • Types of optical filters include color filters, near-infrared cut filters, near-infrared transmission filters, etc., and color filters are preferred.
  • the color filter preferably has the film of the present invention as its pixels, and more preferably has the film of the present invention as its colored pixels.
  • the film thickness of the film of the present invention can be adjusted as appropriate depending on 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 even more preferably 0.3 ⁇ m or more.
  • the width of the pixels included in the optical filter is preferably 0.4 to 10.0 ⁇ m.
  • the lower limit is preferably 0.4 ⁇ m or more, more preferably 0.5 ⁇ m or more, and even more preferably 0.6 ⁇ m or more.
  • the upper limit is preferably 5.0 ⁇ m or less, more preferably 2.0 ⁇ m or less, even more preferably 1.0 ⁇ m or less, and even more preferably 0.8 ⁇ m or less.
  • the Young's modulus of the pixel is preferably 0.5 to 20 GPa, more preferably 2.5 to 15 GPa.
  • each pixel included in the optical filter has high flatness.
  • the surface roughness Ra of the pixel is preferably 100 nm or less, more preferably 40 nm or less, and even more preferably 15 nm or less. Although the lower limit is not specified, it is preferably 0.1 nm or more, for example.
  • the surface roughness of a pixel can be measured using, for example, an AFM (atomic force microscope) Dimension 3100 manufactured by Veeco.
  • the contact angle of water on the pixel can be set to a suitable 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.).
  • the volume resistance value of the pixel is high.
  • the volume resistance value of the pixel is preferably 10 9 ⁇ cm or more, more preferably 10 11 ⁇ cm or more.
  • the upper limit is not specified, it is preferably 10 14 ⁇ cm or less, for example.
  • the volume resistance value of a pixel can be measured using an ultra-high resistance meter 5410 (manufactured by Advantest).
  • a protective layer may be provided on the surface of the film of the present invention.
  • various functions such as oxygen blocking, low reflection, hydrophilic and hydrophobic properties, 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 to 10 ⁇ m, more preferably 0.1 to 5 ⁇ m.
  • Examples of the method for forming the protective layer include a method of applying a composition for forming the protective layer, a chemical vapor deposition method, and a method of pasting a molded resin with an adhesive.
  • Components constituting the protective layer include (meth)acrylic resin, ene thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, 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 include resin, polyacrylonitrile resin, cellulose resin, Si, C, W, Al 2 O 3 , Mo, SiO 2 , Si 2 N 4 and the like, 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 protective layer may contain organic/inorganic fine particles, absorbers for light of specific wavelengths (e.g., ultraviolet rays, near-infrared rays, etc.), refractive index adjusters, antioxidants, adhesives, surfactants, and other additives, as necessary. It may contain.
  • organic/inorganic fine particles include polymer fine particles (e.g., silicone resin fine particles, polystyrene fine particles, melamine resin fine particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, titanium oxynitride. , magnesium fluoride, hollow silica, silica, calcium carbonate, barium sulfate, and the like.
  • the absorber for light of a specific wavelength a known absorber can be used.
  • the content of these additives can be adjusted as appropriate, but is preferably 0.1 to 70% by weight, more preferably 1 to 60% by weight, based on the total weight of the protective layer.
  • the protective layers described in paragraph numbers 0073 to 0092 of JP 2017-151176 A can also be used.
  • the optical filter may have a structure in which each pixel is embedded in a space partitioned into a lattice shape by partition walls, for example.
  • the solid-state imaging device of the present invention has the film of the present invention described above.
  • the configuration of the solid-state image sensor is not particularly limited as long as it functions as a solid-state image sensor, but examples include the following configurations.
  • the substrate has a plurality of photodiodes that constitute the light receiving area of a solid-state image sensor (CCD (charge-coupled device) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.) and a transfer electrode made of polysilicon or the like.
  • a device protective film made of silicon nitride or the like is formed on the light-shielding film to cover the entire surface of the light-shielding film and the light-receiving part of the photodiode. It has a configuration in which a color filter is provided on the device protective film.
  • the color filter may have a structure in which each colored pixel is embedded in a space partitioned, for example, in a lattice shape by partition walls.
  • the partition wall preferably has a lower refractive index than each colored pixel. Examples of imaging devices having such a structure include devices described in Japanese Patent Application Publication No. 2012-227478, Japanese Patent Application Publication No. 2014-179577, and International Publication No.
  • an ultraviolet absorbing layer may be provided within the structure of the solid-state image sensor to improve light resistance.
  • An imaging device equipped with the solid-state imaging device of the present invention can be used not only as a digital camera or an electronic device having an imaging function (such as a mobile phone), but also as an in-vehicle camera or a surveillance camera.
  • the image display device of the present invention has the film of the present invention described above.
  • Examples of the image display device include a liquid crystal display device and an organic electroluminescence display device.
  • Examples of image display devices and details of each image display device see, for example, “Electronic Display Devices (written by Akio Sasaki, Kogyo Chosenkai Co., Ltd., published in 1990)” and “Display Devices (written by Junaki Ibuki, published by Sangyo Tosho)”. Co., Ltd., issued in 1989).
  • liquid crystal display devices are described, for example, in "Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, Kogyo Chosenkai Co., Ltd., published in 1994)".
  • Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, Kogyo Chosenkai Co., Ltd., published in 1994)
  • the present invention can be applied to various types of liquid crystal display devices described in the above-mentioned "Next Generation Liquid Crystal Display Technology.”
  • ⁇ Method for measuring average primary particle diameter of pigments and pigment derivatives Using a transmission electron microscope (TEM), the size of the primary particles of the pigment was directly measured from the photograph taken. Specifically, the minor axis diameter and major axis diameter of each primary particle of the pigment were measured, and the average was taken as the primary particle diameter of the pigment. Next, for the 100 pigment primary particles, the volume of each primary particle was determined by approximating the cube of the particle size of the primary particles, and the volume average particle size was taken as the average primary particle size of the pigment. The average primary particle size of the pigment derivative was also measured in the same manner.
  • TEM transmission electron microscope
  • dispersion liquid (resin composition)> (Prescription 1) A mixed solution of a total of 15.6 parts by mass of pigment and pigment derivative, 3.9 parts by mass of resin, and 80.5 parts by mass of solvent was mixed using a bead mill (zirconia beads 0.1 mm diameter). Time mixed and dispersed. Next, dispersion treatment was performed using a high-pressure dispersion machine NANO-3000-10 (manufactured by Nippon BEE Co., Ltd.) with a pressure reduction mechanism under conditions of a pressure of 2000 kg/cm 2 and a flow rate of 500 g/min. This dispersion process was repeated up to 10 times to obtain a dispersion liquid.
  • NANO-3000-10 manufactured by Nippon BEE Co., Ltd.
  • the pigments, pigment derivatives, resins, and solvents shown in the table below were used.
  • the mixing ratio of pigments in the table below is the value in terms of solid content, and the BET specific surface area of the pigment derivative was measured using the nitrogen adsorption method using an automatic vapor adsorption measuring device ("BELSORP18" manufactured by Bell Japan). This is a value measured based on the BET method.
  • Pigment Blue15:6 blue pigment
  • I. Pigment Violet19 purple pigment
  • I. Pigment Violet23 purple pigment
  • PP-Pig-1 to PP-Pig-22 Compounds with the following structure (near-infrared absorbing pigments)
  • pigment derivative DPP-1 to DPP-30 Compounds with the following structure (pigment derivatives having a diketopyrrolopyrrole structure)
  • PP-1 to PP-29 Compounds with the following structure (pigment derivatives having a pyrrolopyrrole structure)
  • AZM-1 to AZM-36 Complexes of the following metals and the following ligands (pigment derivatives having an azomethine structure)
  • IIN-1 to IIN-3 Compounds with the following structure (pigment derivatives having an isoindoline structure)
  • QP-1 Compound with the following structure (pigment derivative having a quinophthalone structure)
  • AZO-1 Compound with the following structure (pigment derivative having an azo structure)
  • ATQ-1 to ATQ-3 Compounds with the following structure (pigment derivatives having anthraquinone structure)
  • TI-1 Compound with the following structure (pigment derivative having a thiazine indigo structure)
  • QCD-1 Compound with the following structure (pigment derivative having a quinacridone structure)
  • BZI-1 Compound with the following structure (pigment derivative having a benzoindole structure)
  • PC-1 Compound with the following structure (pigment derivative having a phthalocyanine structure)
  • DOZ-1 Compound with the following structure (pigment derivative having a dioxazine structure)
  • TAZ-1 Compound with the following structure (pigment derivative having a triazine structure)
  • (resin) D-1 Resin D-1 synthesized by the following method 50 parts by mass of methyl methacrylate, 30 parts by mass of n-butyl methacrylate, 20 parts by mass of t-butyl methacrylate, and 45.4 parts by mass of propylene glycol monomethyl ether acetate (PGMEA) were charged into a reaction vessel, and the atmosphere was changed to nitrogen gas. Replaced with. The inside of the reaction vessel was heated to 70°C, 6 parts by mass of 3-mercapto-1,2-propanediol was added, and further 0.12 parts by mass of AIBN (azobisisobutyronitrile) was added. Allowed time to react. It was confirmed by solid content measurement that 95% had reacted.
  • PMEA propylene glycol monomethyl ether acetate
  • Resin D-2 Resin D-2 synthesized by the following method 6.0 parts by mass of 3-mercapto-1,2-propanediol, 9.5 parts by mass of pyromellitic anhydride, 62 parts by mass of PGMEA, 1,8-diazabicyclo-[5.4.0]-7 -0.2 parts by mass of undecene was charged into a reaction vessel, and the atmospheric gas was replaced with nitrogen gas. The inside of the reaction vessel was heated to 100° C. and reacted for 7 hours.
  • Resin D-3 Resin D-3 synthesized by the following method Resin D-1 was synthesized in the same manner except that 20 parts by mass of t-butyl methacrylate was changed to 20 parts by mass of (3-ethyloxetan-3-yl)methyl methacrylate, acid value 43 mgKOH/g, weight Resin D-3 having the following structure and having an average molecular weight (Mw) of 9,000 was obtained.
  • Resin D-4 Resin D-4 synthesized by the following method 108 parts by mass of 1-thioglycerol, 174 parts by mass of pyromellitic anhydride, 650 parts by mass of methoxypropyl acetate, and 0.2 parts by mass of monobutyltin oxide as a catalyst were charged into a reaction vessel, and the atmosphere was replaced with nitrogen gas. After the substitution, the mixture was reacted at 120° C. for 5 hours (first step). Acid value measurement confirmed that 95% or more of the acid anhydride was half-esterified.
  • D-5 Resin with the following structure (the numerical value appended to the main chain is the molar ratio, and the numerical value appended to the side chain is the number of repeating units. Weight average molecular weight 16000, acid value 67 mgKOH/g)
  • D-6 Resin with the following structure (the numerical value appended to the main chain is the molar ratio, and the numerical value appended to the side chain is the number of repeating units. Weight average molecular weight 20000, acid value 36 mgKOH/g)
  • D-7 DISPERBYK-111 (manufactured by BYKChemie, acidic dispersant)
  • D-9 Solsperse 20000 (manufactured by Nippon Lubrizol Co., Ltd., basic dispersant)
  • D-11 Resin with the following structure (the numerical value appended to the main chain is the molar ratio, and the numerical value appended to the side chain is the number of repeating units. Weight average molecular weight 18000, acid value 82.1 mgKOH/g)
  • Viscosity change rate (%) (
  • D The viscosity change rate is 15%. more than %
  • the dispersions (resin compositions) of Examples had few coarse particles, excellent stability over time, and excellent pigment dispersion stability.
  • the BET specific surface areas of the pigment derivatives contained in the dispersions of Examples 1 to 181 were within the range of 2 to 300 m 2 /g.
  • the average primary particle diameter of the pigment contained in the dispersions of Examples 1 to 181 is within the range of 10 to 100 nm, and the average primary particle diameter of the pigment derivative is within the range of 5 to 200 nm. It was within the range.
  • the BET specific surface area of the pigment derivative contained in the dispersion liquid of Comparative Example 1 is less than 2 m 2 /g
  • the BET ratio of the pigment derivative contained in the dispersion liquid of Comparative Example 2 is less than 2 m 2 /g.
  • the surface area was over 300 m 2 /g.
  • Dispersion liquid Dispersion liquids 1 to 181, dispersion liquid C1, dispersion liquid C2: Dispersion liquids 1 to 181, dispersion liquid C1, dispersion liquid C2 described above
  • M-1 Compound with the following structure
  • M-2 Compound with the following structure
  • M-3 KAYARAD DPHA (mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate, manufactured by Nippon Kayaku Co., Ltd.)
  • M-4 Compound with the following structure
  • M-5 Mixture of compounds with the following structure (containing 55 mol% to 63 mol% of the compound on the left)
  • M-6 Compound with the following structure.
  • I-1 Irgacure OXE01 (manufactured by BASF, oxime compound)
  • I-2 Irgacure OXE02 (manufactured by BASF, oxime compound)
  • I-3 to I-8 Compounds with the following structure
  • I-10 Omnirad 907 (manufactured by IGM Resins B.V., ⁇ -aminoketone compound)
  • I-11 to I-12 Compounds with the following structure
  • resin B-1 20% by mass PGMEA solution of resin with the following structure (the numbers appended to the main chain are molar ratios; resin having acid groups, weight average molecular weight 11000, acid value 69.2mgKOH/g)
  • B-3 20% by mass of a resin with the following structure (the numerical value appended to the main chain is the molar ratio, and the numerical value appended to the side chain is the number of repeating units.
  • A-1 EHPE3150 (manufactured by Daicel Corporation, 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2'-bis(hydroxymethyl)-1-butanol)
  • UV-1 Compound with the following structure (ultraviolet absorber)
  • surfactant Su-1 KF-6001 (manufactured by Shin-Etsu Chemical Co., Ltd., silicone surfactant, carbinol-modified polydimethylsiloxane at both ends, hydroxyl value 62 mgKOH/g)
  • a base layer forming composition (CT-4000, manufactured by Fujifilm Electronics Materials Co., Ltd.) was coated on a glass substrate using a spin coater to a thickness of 0.1 ⁇ m after post-baking, and coated on a hot plate.
  • a base layer was formed by heating at 220° C. for 1 hour to obtain a glass substrate (support) with a base layer.
  • each resin composition was applied by spin coating so that the film thickness after post-baking was 0.4 ⁇ m. Then, using a hot plate, it was heated at 100° C. for 3 minutes.
  • the glass substrate was placed on the horizontal rotary table of a spin shower developing machine (Model DW-30, manufactured by Chemitronics Co., Ltd.), and a developer (CD-2000, manufactured by Fujifilm Electronics Materials Co., Ltd.) was applied.
  • a spin shower developing machine Model DW-30, manufactured by Chemitronics Co., Ltd.
  • a developer CD-2000, manufactured by Fujifilm Electronics Materials Co., Ltd.
  • puddle development was performed at 23°C for 60 seconds using a Rinsing treatment was performed by supplying water from a jet nozzle in the form of a shower, followed by spray drying.
  • heat treatment post-bake was performed for 5 minutes using a 200° C. hot plate.
  • the absorbance A1 of the glass substrate before applying the resin composition and the absorbance A1 of the glass substrate after post-baking are measured using a spectrophotometer, and the amount of change in absorbance ⁇ A is calculated from the following formula, and the amount of change in absorbance is calculated using the following formula.
  • the development residue was evaluated using the maximum value of ⁇ A. Note that the maximum value of the amount of change in absorbance ⁇ A is the amount of change in absorbance at the wavelength where the amount of change in absorbance ⁇ A is the largest. The smaller the maximum value of the absorbance change amount ⁇ A, the smaller the amount of development residue.
  • Amount of change in absorbance ⁇ A
  • the resin compositions of Examples were able to form pixels with less development residue.
  • the BET specific surface areas of the pigment derivatives contained in the resin compositions of Examples 1001 to 1222 were within the range of 2 to 300 m 2 /g. Further, the average primary particle size of the pigments contained in Examples 1001 to 1222 was within the range of 10 to 100 nm, and the average primary particle size of the pigment derivative was within the range of 5 to 200 nm.
  • the BET specific surface area of the pigment derivative contained in the resin composition of Comparative Example 1001 is less than 2 m 2 /g, and the BET specific surface area of the pigment derivative contained in the resin composition of Comparative Example 1002 exceeds 300 m 2 /g. It was something.
  • Films obtained from the resin compositions of Examples can be suitably used for optical filters, solid-state imaging devices, and image display devices.

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Abstract

La composition de résine comprend un pigment, un dérivé de pigment ayant une surface spécifique BET selon le procédé d'adsorption d'azote de 2 à 300 m2/g, une résine et un solvant. L'invention concerne également un procédé de production d'une composition de résine, et un dérivé de pigment, un film, un filtre optique, un élément d'imagerie à semi-conducteurs et un dispositif d'affichage d'image.
PCT/JP2023/024170 2022-07-11 2023-06-29 Composition de résine, procédé de production d'une composition de résine, dérivé de pigment, film, filtre optique, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image WO2024014300A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003171574A (ja) * 2001-12-06 2003-06-20 Toyo Ink Mfg Co Ltd 水性顔料分散体およびそれを用いたインクジェット記録液
JP2008081705A (ja) * 2006-09-29 2008-04-10 Toray Ind Inc 水性顔料分散液およびそれを用いたインク組成物
JP2013120309A (ja) * 2011-12-08 2013-06-17 Toyo Ink Sc Holdings Co Ltd カラーフィルタ用顔料組成物、着色組成物およびカラーフィルタ
JP2013125265A (ja) * 2011-12-16 2013-06-24 Toyo Ink Sc Holdings Co Ltd カラーフィルタ用赤色着色組成物及びカラーフィルタ

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003171574A (ja) * 2001-12-06 2003-06-20 Toyo Ink Mfg Co Ltd 水性顔料分散体およびそれを用いたインクジェット記録液
JP2008081705A (ja) * 2006-09-29 2008-04-10 Toray Ind Inc 水性顔料分散液およびそれを用いたインク組成物
JP2013120309A (ja) * 2011-12-08 2013-06-17 Toyo Ink Sc Holdings Co Ltd カラーフィルタ用顔料組成物、着色組成物およびカラーフィルタ
JP2013125265A (ja) * 2011-12-16 2013-06-24 Toyo Ink Sc Holdings Co Ltd カラーフィルタ用赤色着色組成物及びカラーフィルタ

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