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WO2025041643A1 - Composition durcissable, film, filtre optique, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image - Google Patents

Composition durcissable, film, filtre optique, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image Download PDF

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Publication number
WO2025041643A1
WO2025041643A1 PCT/JP2024/028609 JP2024028609W WO2025041643A1 WO 2025041643 A1 WO2025041643 A1 WO 2025041643A1 JP 2024028609 W JP2024028609 W JP 2024028609W WO 2025041643 A1 WO2025041643 A1 WO 2025041643A1
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WO
WIPO (PCT)
Prior art keywords
group
curable composition
pigment
formula
compound
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Pending
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PCT/JP2024/028609
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English (en)
Japanese (ja)
Inventor
憲晃 佐藤
俊佑 柳
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Fujifilm Corp
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Fujifilm Corp
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Publication of WO2025041643A1 publication Critical patent/WO2025041643A1/fr
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • 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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds

Definitions

  • the present invention relates to a curable composition containing a pigment.
  • the present invention also relates to a film, an optical filter, a solid-state imaging device, and an image display device that use the curable composition containing a pigment.
  • Color filters are manufactured using a curable composition that contains coloring materials such as pigments.
  • the pigment is dispersed in the curable composition using a dispersant or the like in order to improve the stability of the curable composition over time.
  • Patent Document 1 describes a dispersant represented by the following formula.
  • the colorant concentration of the curable composition is increased, the amount of materials other than the colorant is relatively reduced, so the colorant tends to aggregate during storage of the curable composition, and the viscosity of the curable composition tends to increase over time. Furthermore, when pixels are formed by photolithography using the curable composition, development residues tend to be generated between pixels.
  • an object of the present invention is to provide a curable composition having excellent storage stability and developability. Another object of the present invention is to provide a film, an optical filter, a solid-state imaging device, and an image display device.
  • the present invention provides the following.
  • a curable composition including a colorant including a pigment, a polymerizable compound, a photopolymerization initiator, and a compound represented by formula (1);
  • X1 represents an (m+n) valent linking group having a molecular weight of 1,000 or less
  • Y 1 represents -O- or -NR Y1 -
  • R Y1 represents a hydrogen atom or a substituent
  • Z1 represents a polyether structure
  • R 1 represents an alkyl group or an aryl group
  • m and n each independently represent an integer of 1 to 10.
  • X 1 in the above formula (1) is a linking group having a molecular weight of 50 to 250 and a valence of m+n, R1 is an alkyl group or an aryl group; Z1 is a polyalkylene glycol structure having a molecular weight of 300 to 5000; m and n are each independently 2 or 3;
  • X 1 in the above formula (1) is a linking group having a molecular weight of 50 to 250 and a valence of m+n, R 1 is a linear alkyl group having 1 to 20 carbon atoms or a branched alkyl group having 3 to 20 carbon atoms; Z1 includes a structure represented by formula (Z1-1), m and n are each independently 2 or 3; The curable composition according to ⁇ 1> or ⁇ 2>, wherein the pKa of the compound represented by formula (1) is 1.0 to 3.0; In formula (Z1-1), p1 represents an integer of 5 to 90.
  • ⁇ 6> The curable composition according to any one of ⁇ 1> to ⁇ 5>, wherein R 1 in the above formula (1) is a linear or branched alkyl group having 4 to 18 carbon atoms.
  • R 1 in the above formula (1) is a linear or branched alkyl group having 4 to 18 carbon atoms.
  • ⁇ 7> The curable composition according to any one of ⁇ 1> to ⁇ 6>, wherein m+n in the formula (1) is 6.
  • ⁇ 8> The curable composition according to any one of ⁇ 1> to ⁇ 7>, further comprising 10 to 40 parts by mass of the compound represented by formula (1) relative to 100 parts by mass of the pigment.
  • ⁇ 9> The curable composition according to any one of ⁇ 1> to ⁇ 8>, wherein the pigment includes a diketopyrrolopyrrole pigment and a phthalocyanine pigment.
  • ⁇ 10> A film obtained by using the curable composition according to any one of ⁇ 1> to ⁇ 9>.
  • ⁇ 11> An optical filter having the film according to ⁇ 10>.
  • ⁇ 12> A solid-state imaging device comprising the film according to ⁇ 10>.
  • ⁇ 13> An image display device having the film according to ⁇ 10>.
  • the present invention can provide a curable composition with excellent storage stability and developability.
  • the present invention can also provide a film, an optical filter, a solid-state imaging device, and an image display device.
  • alkyl group encompasses not only alkyl groups that have no substituents (unsubstituted alkyl groups) but also alkyl groups that have substituents (substituted alkyl groups).
  • exposure includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams.
  • Examples of light used for exposure include the bright line spectrum of a mercury lamp, far ultraviolet light represented by an excimer laser, extreme ultraviolet light (EUV light), X-rays, active rays or radiation such as electron beams.
  • (meth)acrylate refers to both or either of acrylate and methacrylate
  • (meth)acrylic refers to both or either of acrylic and methacrylic
  • (meth)acryloyl refers to both or either of acryloyl and methacryloyl.
  • Me represents a methyl group
  • Et represents an ethyl group
  • Bu represents a butyl group
  • Ph represents a phenyl group.
  • the weight average molecular weight and number average molecular weight are values calculated as polystyrene standards measured by GPC (gel permeation chromatography).
  • the total solids content refers to the total mass of all components of the composition excluding the solvent.
  • a pigment means a coloring material that is difficult to dissolve in a solvent.
  • the term "process” refers not only to an independent process, but also to a process that cannot be clearly distinguished from other processes, as long as the process achieves its intended effect.
  • the curable composition of the present invention is characterized by containing a coloring material containing a pigment, a polymerizable compound, a photopolymerization initiator, and a compound represented by formula (1).
  • the carboxy group portion is adsorbed to the pigment surface. It is also presumed that the "Z 1 -R 1 " portion of formula (1) acts as a steric repulsive group. Since Z 1 is a polyether structure, it is presumed that it has high compatibility with the dispersion solvent and can enhance dispersibility. Therefore, in the curable composition, the compound represented by formula (1) can efficiently suppress pigment aggregation and suppress an increase in the viscosity of the curable composition over time. Therefore, the curable composition of the present invention has excellent storage stability. In addition, since formula (1) has a carboxy group and Z1 is a polyether structure, it has good affinity with the developer.
  • the curable composition of the present invention has excellent developability and can effectively suppress the generation of development residues.
  • the curable composition of the present invention is preferably used as a curable composition for optical filters.
  • optical filters include color filters, infrared transmission filters, and infrared cut filters, and color filters are preferred.
  • the curable composition of the present invention is also preferably used for solid-state imaging devices. More specifically, it is preferably used as a curable composition for optical filters used in solid-state imaging devices, and is even more preferably used as a curable composition for forming colored pixels of color filters used in solid-state imaging devices.
  • color filter is a filter having colored pixels that transmit light of a specific wavelength.
  • colored pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, and yellow pixels, and green pixels, red pixels, or blue pixels are preferred, and green pixels or red pixels are more preferred.
  • the maximum absorption wavelength of the infrared cut filter is preferably in the wavelength range of 700 to 1800 nm, more preferably in the wavelength range of 700 to 1300 nm, and even more preferably in the wavelength range of 700 to 1000 nm.
  • the transmittance of the infrared cut filter in 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 infrared cut filter to the absorbance A550 at a wavelength of 550 nm is preferably 20 to 500, more preferably 50 to 500, even more preferably 70 to 450, and particularly preferably 100 to 400.
  • the infrared cut filter can be formed using a curable composition containing an infrared absorbing pigment.
  • the infrared transmission filter is a filter that transmits at least a part of infrared light.
  • the infrared transmission filter is preferably a filter that blocks at least a part of visible light and transmits at least a part of infrared light.
  • Preferred examples of the infrared transmission filter include filters that satisfy the spectral characteristics of 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 minimum transmittance of 70% or more (preferably 75% or more, more preferably 80% or more) in the wavelength range of 1100 to 1300 nm.
  • the infrared transmission filter is preferably a filter that satisfies any one of the following spectral characteristics (1) to (5).
  • the curable composition of the present invention can also be used as a light-shielding film.
  • the solids concentration of the curable composition of the present invention is preferably 5 to 30% by mass.
  • the lower limit is preferably 7.5% by mass or more, and 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 curable composition of the present invention contains a coloring material.
  • the coloring material include a white coloring material, a black coloring material, a chromatic coloring material, and an infrared absorbing coloring material.
  • a pigment derivative can also be used as the coloring material.
  • the white coloring material includes not only pure white coloring materials, but also light gray coloring materials close to white (e.g., grayish white, light gray, etc.).
  • the coloring material contained in the curable composition of the present invention is a pigment.
  • the pigment may be either an inorganic pigment or an organic pigment, but from the standpoint of color variation, ease of dispersion, safety, etc., it is preferable for the pigment to be an organic pigment.
  • the coloring material preferably contains at least one selected from phthalocyanine pigments, dioxazine pigments, quinacridone pigments, anthraquinone pigments, perylene pigments, azo pigments, azomethine pigments, diketopyrrolopyrrole pigments, pyrrolopyrrole pigments, isoindoline pigments, and quinophthalone pigments, more preferably contains at least one selected from phthalocyanine pigments and diketopyrrolopyrrole pigments, isoindoline pigments, quinophthalone pigments, and azo pigments, and even more preferably contains phthalocyanine pigments and diketopyrrolopyrrole pigments because the effects of the present invention are more pronounced.
  • the average primary particle diameter of the pigment and pigment derivative is preferably 1 to 200 nm.
  • the lower limit is preferably 5 nm or more, more preferably 10 nm or more.
  • the upper limit is preferably 180 nm or less, more preferably 150 nm or less, and even more preferably 100 nm or less.
  • the primary particle diameter of the pigment and pigment derivative can be determined from a photograph obtained by observing the primary particles of the pigment and pigment derivative with a transmission electron microscope. Specifically, the projected area of the primary particles of the pigment is determined, and the corresponding circle equivalent diameter is calculated as the primary particle diameter of the pigment.
  • the average primary particle diameter in the present invention is the arithmetic mean value of the primary particle diameters of 400 primary particles of the pigment.
  • the primary particles of the pigment refer to independent particles without aggregation. The same applies to the average primary particle diameter of the pigment derivative.
  • the crystallite size of the pigment and pigment derivative is preferably 0.1 to 50 nm, more preferably 0.5 to 30 nm, and even more preferably 1 to 15 nm.
  • the crystallite size can be determined from the half-width of the diffraction angle peak using an X-ray diffraction device, and is calculated using Scherrer's formula.
  • the crystallite size of the organic pigment and pigment derivative can be adjusted by known methods such as adjusting the production conditions or grinding after production.
  • the specific surface area of the pigment and pigment derivative 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 value of the specific surface area can be measured according to DIN 66131: determination of the specific surface area of solids by gas adsorption in accordance with the BET (Brunauer, Emmett and Teller) method.
  • the coloring material contained in the curable composition of the present invention preferably contains a pigment and a pigment derivative.
  • the pigment derivative include compounds having a structure in which an acid group or a basic group is bonded to a colorant skeleton. Details of the pigment derivative will be described later.
  • the content of the pigment derivative is preferably 1 to 30 parts by mass, and more preferably 3 to 20 parts by mass, per 100 parts by mass of the pigment. Only one type of pigment derivative may be used, or two or more types may be used in combination.
  • the coloring material contained in the curable composition of the present invention may contain a pigment and a dye.
  • the content of the dye is preferably 10 to 100 parts by mass relative to 100 parts by mass of the pigment.
  • the upper limit is preferably 80 parts by mass or less, and more preferably 70 parts by mass or less.
  • the lower limit is preferably 20 parts by mass or more, more preferably 30 parts by mass or more, and even more preferably 40 parts by mass or more. Only one type of dye may be used, or two or more types may be used in combination.
  • the coloring material contained in the curable composition of the present invention is substantially free of dye. According to this embodiment, a film having excellent light resistance and heat resistance can be formed. "Substantially free of dye” means that the content of dye in the coloring material is 0.1% by mass or less, preferably 0.01% by mass or less, and more preferably no dye is contained.
  • chromatic colorants examples include colorants having a maximum absorption wavelength in the wavelength range of 400 to 700 nm. Examples include yellow colorants, orange colorants, red colorants, green colorants, purple colorants, and blue colorants.
  • the chromatic colorant is preferably a pigment (chromatic pigment), more preferably a red pigment, yellow pigment, or blue pigment, and even more preferably a red pigment or blue pigment. Specific examples of chromatic pigments include those shown below.
  • the red colorant may be a diketopyrrolopyrrole compound, anthraquinone compound, an azo compound, a naphthol compound, an azomethine compound, a xanthene compound, a quinacridone compound, a perylene compound, or a thioindigo compound.
  • a diketopyrrolopyrrole compound, an anthraquinone compound, or an azo compound is preferable, and a diketopyrrolopyrrole compound is more preferable.
  • the red colorant is preferably a red pigment.
  • the red pigment is preferably a diketopyrrolopyrrole pigment.
  • red colorants 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,
  • red pigments include 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, and 297.
  • red colorant a compound described in paragraph 0034 of International Publication No. 2022/085485 and a brominated diketopyrrolopyrrole compound described in JP-A-2020-085947 can also be used.
  • C.I. Pigment Red 122, 177, 224, 254, 255, 264, 269, and 272 are preferred, and C.I. Pigment Red 254, 264, and 272 are more preferred.
  • Green colorants include phthalocyanine compounds and squarylium compounds, with phthalocyanine compounds being preferred.
  • the green colorant is preferably a green pigment.
  • the green pigment is preferably a phthalocyanine pigment.
  • green colorants include green pigments such as C.I. Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65, and 66.
  • halogenated zinc phthalocyanine pigments having an average of 10 to 14 halogen atoms, an average of 8 to 12 bromine atoms, and an average of 2 to 5 chlorine atoms in one molecule can also be used as green colorants.
  • Specific examples include the compounds described in WO 2015/118720.
  • compounds described in paragraph 0029 of WO 2022/085485, aluminum phthalocyanine compounds described in JP 2020-070426 A, and diarylmethane compounds described in JP 2020-504758 A can also be used as green colorants.
  • C.I. Pigment Green 7, 36, 58, 62, and 63 are preferred, and C.I. Pigment Green 36 and 58 are more preferred.
  • Orange colorants include diketopyrrolopyrrole compounds and azo compounds, and are preferably diketopyrrolopyrrole compounds.
  • the orange colorant is preferably an orange pigment.
  • the orange pigment is preferably a diketopyrrolopyrrole pigment.
  • Specific examples of orange colorants include orange pigments such as C.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, and 73.
  • yellow colorants examples include azo compounds, azomethine compounds, isoindoline compounds, pteridine compounds, quinophthalone compounds, and perylene compounds.
  • the yellow colorant is preferably a yellow pigment.
  • the yellow pigment is preferably at least one selected from isoindoline pigments, quinophthalone pigments, and azo pigments. Specific examples of yellow colorants include C.I.
  • an azobarbituric acid nickel complex having the following structure can also be used.
  • the compounds described in paragraphs 0031 to 0033 of WO 2022/085485, the methine dyes described in JP 2019-073695 A, and the methine dyes described in JP 2019-073696 A can be used.
  • purple colorants examples include oxazine compounds, quinacridone compounds, perylene compounds, and indigo compounds, with oxazine compounds being preferred.
  • the purple colorant is preferably a purple pigment.
  • Specific examples of purple colorants include purple pigments such as C.I. Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, and 61.
  • blue colorants include phthalocyanine compounds and squarylium compounds, and are preferably phthalocyanine compounds.
  • the blue colorant is preferably a blue pigment.
  • the blue pigment is preferably a phthalocyanine pigment.
  • Specific examples of blue colorants include blue pigments such as 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, and 88.
  • Aluminum phthalocyanine compounds having phosphorus atoms can also be used as blue colorants. Specific examples include the compounds described in paragraphs 0022 to 0030 of JP-A No. 2012-247591 and paragraph 0047 of JP-A No. 2011-157478.
  • Dyes can also be used as chromatic colorants.
  • the dyes there are no particular limitations on the dyes, and any known dyes can be used. Examples include pyrazole azo dyes, anilino azo dyes, triarylmethane dyes, anthraquinone dyes, anthrapyridone dyes, benzylidene dyes, oxonol dyes, pyrazolotriazole azo dyes, pyridone azo dyes, cyanine dyes, phenothiazine dyes, pyrrolopyrazole azomethine dyes, xanthene dyes, phthalocyanine dyes, benzopyran dyes, indigo dyes, and pyrromethene dyes.
  • a dye polymer can also be used as a chromatic colorant.
  • the dye polymer is preferably a dye dissolved in a solvent.
  • the dye polymer may form particles. When the dye polymer is a particle, it is usually used in a state dispersed in a solvent.
  • a particulate dye polymer can be obtained by, for example, emulsion polymerization, and examples of the compound and manufacturing method described in JP-A-2015-214682 include the compound and manufacturing method described in JP-A-2015-214682.
  • the dye polymer has two or more dye structures in one molecule, and preferably has three or more dye structures. There is no particular limit to the upper limit, but it can be 100 or less.
  • the multiple dye structures in one molecule may be the same dye structure or different dye structures.
  • the weight average molecular weight (Mw) of the dye polymer 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 may be a compound described in JP2011-213925A, JP2013-041097A, JP2015-028144A, JP2015-030742A, WO2016/031442, etc.
  • chromatic colorants there may be mentioned a triarylmethane dye polymer described in Korean Patent Publication No. 10-2020-0028160, a xanthene compound described in JP 2020-117638 A, a phthalocyanine compound described in WO 2020/174991 A, an isoindoline compound or a salt thereof described in JP 2020-160279 A, a compound represented by formula 1 described in Korean Patent Publication No. 10-2020-0069442 A, a compound represented by formula 1 described in Korean Patent Publication No. 10-2020-0069730 A, a compound represented by formula 1 described in Korean Patent Publication No. 10-2020-0069070 A, Compounds represented by formula 1 described in Korean Patent Publication No.
  • 10-2020-0069067 compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069062, halogenated zinc phthalocyanine pigments described in Japanese Patent No. 6809649, isoindoline compounds described in JP-A-2020-180176, phenothiazine compounds described in JP-A-2021-187913, halogenated zinc phthalocyanines described in WO 2022/004261, and halogenated zinc phthalocyanines described in WO 2021/250883 can be used.
  • the other colorant may be a rotaxane, and the dye skeleton may be used in the cyclic structure of the rotaxane, may be used in the rod-shaped structure, or may be used in both structures.
  • colorants include quinophthalone compounds represented by formula 1 in Korean Patent Publication No. 10-2020-0030759, polymer dyes described in Korean Patent Publication No. 10-2020-0061793, colorants described in JP-A-2022-029701, isoindoline compounds described in WO 2022/014635, aluminum phthalocyanine compounds described in WO 2022/024926, compounds described in JP-A-2022-045895, compounds described in WO 2022/050051, compounds described in JP-A-2020-090676, compounds described in JP-A-2020-055956, Compounds described in JP 2021-031681 A, compounds described in JP 2022-056354 A, compounds described in US Patent Application Publication No.
  • Two or more chromatic coloring materials may be used in combination.
  • the combination of two or more chromatic coloring materials may form a black color. Examples of such combinations include the following embodiments (1) to (7).
  • the curable composition of the present invention can be preferably used as a curable composition for forming an infrared transmission filter.
  • An embodiment containing a red color material, a blue color material, a yellow color material, and a purple color material (3) An embodiment containing a red color material, a blue color material, a yellow color material, and a purple color material. (4) An embodiment containing a red color material, a blue color material, a yellow color material, a purple color material, and a green color material. (5) An embodiment containing a red color material, a blue color material, a yellow color material, and a green color material. (6) An embodiment containing a red color material, a blue color material, and a green color material. (7) An embodiment containing a yellow color material and a purple color material.
  • the white coloring material examples include inorganic pigments such as 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, and zinc sulfide.
  • the white coloring material can be the white pigment described in paragraphs 0040 to 0043 of WO 2022/085485.
  • the black coloring material is not particularly limited, and any known material can be used.
  • the black coloring material may be an inorganic black coloring material or an organic black coloring material.
  • the black coloring material is preferably a pigment.
  • the black coloring material means a coloring material that exhibits absorption over the entire wavelength range of 400 to 700 nm.
  • inorganic black coloring materials include carbon black, titanium black, graphite, etc., with carbon black and titanium black being preferred, and titanium black being more preferred. Titanium black is black particles containing titanium atoms, and low-order titanium oxide and titanium oxynitride are preferred. As titanium black, titanium black described in paragraph 0044 of WO 2022/085485 can be used. Zirconium nitride powder described in JP 2023-048173 A can also be used as an inorganic black coloring material.
  • organic black colorants examples include bisbenzofuranone compounds, azomethine compounds, perylene compounds, and azo compounds, with bisbenzofuranone compounds and perylene compounds being preferred.
  • organic black colorant the compounds described in paragraph number 0166 of International Publication No. 2022/065215 can be used.
  • perylene black Liogen Black FK4280, etc.
  • perylene black described in paragraphs 0016 to 0020 of JP-A-2017-226821
  • black azo pigments described in JP-A-2022-121935 may also be used.
  • the ratio A 1 /A 2 between the absorbance A 1 at a wavelength of 500 nm of the infrared absorbing colorant and the absorbance A 2 at the maximum absorption wavelength is preferably 0.08 or less, more preferably 0.04 or less.
  • the infrared absorbing colorant is preferably a pigment, more preferably an organic pigment.
  • Examples of infrared absorbing colorants include the compound described in paragraph 0121 of WO 2022/065215, the squarylium compound described in JP 2020-075959 A, the copper complex described in Korean Patent Publication No. 10-2019-0135217 A, the croconic acid compound described in JP 2021-195515 A, the near infrared absorbing dye described in JP 2022-022070 A, the croconium compound described in WO 2019/021767 A, and the compound described in JP 2019-127549 A.
  • a pigment derivative can also be used as the coloring material.
  • the pigment derivative include a compound having a structure in which an acid group or a basic group is bonded to a color skeleton.
  • Examples of the pigment skeletons that make up the pigment derivatives include a quinoline dye skeleton, a benzimidazolone dye skeleton, a benzisoindole dye skeleton, a benzothiazole dye skeleton, an iminium dye skeleton, a squarylium dye skeleton, a croconium dye skeleton, an oxonol dye skeleton, a pyrrolopyrrole dye skeleton, a diketopyrrolopyrrole dye skeleton, an azo dye skeleton, an azomethine dye skeleton, a phthalocyanine dye skeleton, a naphthalocyanine dye skeleton, an anthraquinone dye skeleton, a quinacridone dye skeleton, a dioxazine dye skeleton, a perinone dye skeleton, a perylene dye skeleton, a thioindigo dye ske
  • the content of the colorant in the total solid content of the curable composition is preferably 50% by mass or more, more preferably 55% by mass or more, and even more preferably 60% by mass or more.
  • the upper limit is preferably 80% by mass or less, more preferably 77.5% by mass or less, and even more preferably 75% by mass or less.
  • the molecular weight of the polymerizable compound is preferably 100 to 2500.
  • the upper limit is preferably 2000 or less, and more preferably 1500 or less.
  • the lower limit is preferably 150 or more, and more preferably 250 or more.
  • the polymerizable compound is preferably a compound containing 3 or more ethylenically unsaturated bond-containing groups, more preferably a compound containing 3 to 15 ethylenically unsaturated bond-containing groups, and even more preferably a compound containing 3 to 6 ethylenically unsaturated bond-containing groups.
  • the polymerizable compound is preferably a 3-15 functional (meth)acrylate compound, and more preferably a 3-6 functional (meth)acrylate compound.
  • Specific examples of the polymerizable compound include the compounds described in paragraphs 0075 to 0083 of WO 2022/065215 and the compounds described in Taiwan Patent Application Publication No. 201832008.
  • Preferred polymerizable compounds include dipentaerythritol tri(meth)acrylate (commercially available product is KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetra(meth)acrylate (commercially available product is KAYARAD D-320; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol penta(meth)acrylate (commercially available product is KAYARAD D-310; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa(meth)acrylate (commercially available products are KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd., and NK Ester A-DPH-12E; manufactured by Shin-Nakamura Chemical Co., Ltd.), and compounds in which the (meth)acryloyl groups are bonded via ethylene glycol and/or propylene glycol residues (e.g.,
  • polymerizable compounds examples include diglycerol EO (ethylene oxide) modified (meth)acrylate (commercially available product is M-460; manufactured by Toagosei Co., Ltd.), pentaerythritol tetraacrylate (NK Ester A-TMMT, manufactured by Shin-Nakamura Chemical Co., Ltd.), 1,6-hexanediol diacrylate (KAYARAD HDDA, manufactured by Nippon Kayaku Co., Ltd.), RP-1040 (manufactured by Nippon Kayaku Co., Ltd.), Aronix TO-2349 (manufactured by Toagosei Co., Ltd.), and NK Oligo UA-7200 (manufactured by Shin-Nakamura Chemical Co., Ltd.).
  • diglycerol EO ethylene oxide
  • methacrylate commercially available product is M-460; manufactured by Toagosei Co., Ltd.
  • NK Ester A-TMMT pentaerythri
  • the content of the polymerizable compound in the total solid content of the curable composition is preferably 1 to 35 mass%.
  • the upper limit is preferably 30 mass% or less, more preferably 25 mass% or less, even more preferably 20 mass% or less, and particularly preferably 10 mass% or less.
  • the lower limit is preferably 2 mass% or more, and more preferably 5 mass% or more.
  • the curable composition of the present invention may contain only one type of polymerizable compound, or may contain two or more types. When two or more types of polymerizable compounds are contained, it is preferable that the total amount thereof is within the above range.
  • the curable composition of the present invention contains a photopolymerization initiator.
  • the photopolymerization initiator is not particularly limited and can be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light rays in the ultraviolet to visible regions is preferred.
  • the photopolymerization initiator is preferably a photoradical polymerization initiator.
  • Photopolymerization initiators include halogenated hydrocarbon derivatives (e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, etc.
  • halogenated hydrocarbon derivatives e.g., compounds having a triazine skeleton, compounds having 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, etc.
  • the photopolymerization initiator is preferably a trihalomethyltriazine compound, a benzyl dimethyl ketal compound, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, an acylphosphine compound, a phosphine oxide compound, a metallocene compound, an oxime compound, a hexaarylbiimidazole compound, an onium compound, a benzothiazole compound, a benzophenone compound, an acetophenone compound, a cyclopentadiene-benzene-iron complex, a halomethyloxadiazole compound, or a 3-aryl substituted coumarin compound, more preferably a compound selected from an oxime compound, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, and an acylphosphine compound, and even more preferably an oxime compound.
  • examples of the photopolymerization initiator include the compounds described in paragraphs 0065 to 0111 of JP 2014-130173 A, the compounds described in Japanese Patent No. 6301489 A, and the compounds described in MATERIAL STAGE 37 to 60p, vol. 19, No.
  • Examples of the photopolymerization initiator include the compound described in WO 2019/013112, the compound having a triarylamine or N-arylcarbazole skeleton described in paragraphs 0042 to 0062 of WO 2019/013112, the oxime ester-based photopolymerization initiator described in Japanese Patent Publication No. 7219378, the photopolymerization initiator described in Korean Patent Publication No. 10-2021-0146174, the photopolymerization initiator described in WO 2019/013112, and the photopolymerization initiator described in JP 2023-033731.
  • hexaarylbiimidazole compounds include 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1'-biimidazole.
  • ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (all manufactured by IGM Resins B.V.), Irgacure 184, Irgacure 1173, Irgacure 2959, Irgacure 127 (all manufactured by BASF), etc.
  • Commercially available ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (all manufactured by IGM Resins B.V.), Irgacure 907, Irgacure 369, Irgacure 369E, Irgacure 379EG (all manufactured by BASF), etc.
  • Commercially available acylphosphine compounds include Omnirad 819, Omnirad TPO (all manufactured by IGM Resins B.V.), Irgacure 819, Irgacure TPO (all manufactured by BASF), etc.
  • Examples of oxime compounds include the compound described in paragraph 0142 of WO 2022/085485, the compound described in Japanese Patent No. 5,430,746, the compound described in Japanese Patent No. 5,647,738, the compound represented by general formula (1) and the compounds described in paragraphs 0022 to 0024 of JP 2021-173858 A, the compound represented by general formula (1) and the compounds described in paragraphs 0117 to 0120 of JP 2021-170089 A, and the like.
  • oxime compound examples 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.
  • an oxime compound having a fluorene ring an oxime compound having a skeleton in which at least one benzene ring of a carbazole ring is replaced with a naphthalene ring, an oxime compound having a fluorine atom, an oxime compound having a nitro group, an oxime compound having a benzofuran skeleton, an oxime compound in which a substituent having a hydroxyl group is bonded to a carbazole skeleton, or a compound described in paragraphs 0143 to 0149 of WO 2022/085485 can be used.
  • a compound represented by formula (OX-1) can also be used.
  • X 1a represents a divalent linking group containing at least one ring selected from the group consisting of an aromatic ring and a heterocycle;
  • R 1a represents a hydrogen atom or an acyl group;
  • R2a represents an alkyl group or an aryl group;
  • R 3a and R 4a each independently represent a hydrogen atom or an alkyl group;
  • Alk 1 and Alk 2 each independently represent an alkyl group;
  • R 3a and R 4a may be bonded to form a ring;
  • Alk 1 and Alk 2 may be linked to form a ring;
  • n represents 0 or 1.
  • Examples of the divalent linking group represented by X 1a in formula (OX-1) include a divalent aromatic ring group, a divalent heterocyclic group, a divalent group in which two or more aromatic rings are bonded via a single bond or a linking group, a divalent group in which two or more heterocycles are bonded via a single bond or a linking group, and a divalent group in which an aromatic ring and a heterocycle are bonded via a single bond or a linking group.
  • Examples of the linking group that bonds the above-mentioned aromatic rings, heterocyclic groups, or aromatic rings and heterocycles include -CH 2 -, -O-, -CO-, -S-, -NR x -, and groups combining these.
  • R x represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, or a heterocyclic group.
  • X 1 in formula (OX-1) is preferably a group represented by any one of formulas (X-1) to (X-13), more preferably a group represented by formula (X-1), formula (X-2), formula (X-4), formula (X-6) or formula (X-8), and further preferably a group represented by formula (X-2) or formula (X-6).
  • R X1 to R X9 each independently represent a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group or a heterocyclic group.
  • the number of carbon atoms in the alkyl group represented by R X1 to R X9 is preferably 1 to 15, and more preferably 1 to 10.
  • the alkyl group may be linear, branched, or cyclic.
  • the alkyl group may have a substituent. Examples of the substituent include a halogen atom, an aryl group, and a heterocyclic group.
  • the number of carbon atoms in the alkenyl group represented by R X1 to R X9 is preferably 2 to 15, and more preferably 2 to 10.
  • the alkenyl group may be linear, branched, or cyclic.
  • the alkenyl group may have a substituent. Examples of the substituent include a halogen atom, an aryl group, and a heterocyclic group.
  • the number of carbon atoms in the alkynyl group represented by R X1 to R X9 is preferably 2 to 15, and more preferably 2 to 10.
  • the alkynyl group may be linear, branched, or cyclic.
  • the alkynyl group may have a substituent. Examples of the substituent include a halogen atom, an aryl group, and a heterocyclic group.
  • the number of carbon atoms in the aryl group represented by R X1 to R X9 is preferably 6 to 20, more preferably 6 to 12, still more preferably 6 to 10, and particularly preferably 6.
  • the aryl group may have a substituent. Examples of the substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, and a heterocyclic group.
  • the heterocyclic group represented by R X1 to R X9 is preferably a 5-membered or 6-membered ring.
  • the heteroatoms contained in the heterocyclic group are preferably an oxygen atom, a nitrogen atom, or a sulfur atom.
  • the number of heteroatoms contained in the heterocyclic group is preferably 1 to 3.
  • the heterocyclic group may have a substituent. Examples of the substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, and an aryl group.
  • R 1a represents a hydrogen atom or an acyl group, and is preferably an acyl group.
  • the acyl group represented by R 1a is preferably a group represented by —C(O)—R 101.
  • R 101 represents an aryl group or a heterocyclic group, and is preferably an aryl group.
  • the number of carbon atoms of the aryl group represented by R 101 is preferably 6 to 20, and more preferably 6 to 12.
  • the aryl group may have a substituent. Examples of the substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, and a heterocyclic group.
  • the aryl group represented by R 101 is preferably a phenyl group, a methylphenyl group, or a naphthyl group, and more preferably a methylphenyl group or a naphthyl group.
  • the heterocyclic group represented by R 101 is preferably a 5-membered or 6-membered ring.
  • the heteroatoms contained in the heterocyclic group are preferably an oxygen atom, a nitrogen atom, or a sulfur atom.
  • the number of heteroatoms contained in the heterocyclic group is preferably 1 to 3.
  • the heterocyclic group may have a substituent. Examples of the substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, and an aryl group.
  • R 2a in formula (OX-1) represents an alkyl group or an aryl group, and is preferably an alkyl group because the reactivity of the generated radical is high.
  • the number of carbon atoms of the alkyl group represented by R 2a is preferably 1 to 15, more preferably 1 to 10, even more preferably 1 to 5, and even more preferably 1 to 3.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the alkyl group may have a substituent, but is preferably an unsubstituted alkyl group.
  • the alkyl group represented by R 2a is preferably an unsubstituted linear or branched alkyl group, and more preferably an unsubstituted linear alkyl group.
  • the number of carbon atoms in the aryl group represented by R 2a is preferably 6 to 20, more preferably 6 to 12, still more preferably 6 to 10, and particularly preferably 6.
  • the aryl group may have a substituent, but is preferably an unsubstituted aryl group.
  • R 3a and R 4a each independently represent a hydrogen atom or an alkyl group, and preferably a hydrogen atom.
  • the number of carbon atoms in the alkyl group represented by R 3a and R 4a is preferably 1 to 15, more preferably 1 to 10, even more preferably 1 to 5, and even more preferably 1 to 3.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the alkyl group may have a substituent, but is preferably an unsubstituted alkyl group.
  • R3a and R4a may be bonded to form a ring.
  • the ring formed is preferably a 5- or 6-membered ring, and more preferably a 5- or 6-membered aliphatic hydrocarbon ring.
  • Alk 1 and Alk 2 each independently represent an alkyl group.
  • the number of carbon atoms in the alkyl group is preferably 1 to 15, more preferably 1 to 10, even more preferably 1 to 5, and even more preferably 1 to 3.
  • the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
  • the alkyl group may have a substituent, but is preferably an unsubstituted alkyl group.
  • Alk1 and Alk2 may be bonded to form a ring, and preferably form a ring.
  • the ring formed is preferably a 5- or 6-membered ring, more preferably a 5- or 6-membered aliphatic hydrocarbon ring, and more preferably a cyclopentane ring or a cyclohexane ring.
  • n 0 or 1, and is preferably 0.
  • Examples of the substituent represented by R 1b and R 2b include an alkyl group and an aryl group, and an alkyl group is preferable.
  • the number of carbon atoms of the alkyl group is preferably 1 to 15, and more preferably 1 to 10.
  • the alkyl group may be linear, branched, or cyclic.
  • the alkyl group may have a substituent.
  • Examples of the substituent include a halogen atom, an aryl group, an alkenyl group, an alkynyl group, and a heterocyclic group.
  • the number of carbon atoms of the aryl group is preferably 6 to 20, more preferably 6 to 12, even more preferably 6 to 10, and particularly preferably 6.
  • the aryl group may have a substituent. Examples of the substituent include a halogen atom, an alkyl group, an alkenyl group, an alkynyl group, and a heterocyclic group.
  • examples of the resin include the resin described in paragraphs 0091 to 0099 of WO 2022/065215, the blocked polyisocyanate resin described in JP 2016-222891 A, the resin described in JP 2020-122052 A, the resin described in JP 2020-111656 A, the resin described in JP 2020-139021 A, the resin described in JP 2017-138503 A containing a structural unit having a ring structure in the main chain and a structural unit having a biphenyl group in the side chain, and the resin described in paragraphs 0199 to 0199 of JP 2020-186373 A.
  • the resin having a basic group may be a block copolymer (B) described in paragraphs 0063 to 0112 of JP 2014-219665 A, a block copolymer A1 described in paragraphs 0046 to 0076 of JP 2018-156021 A, or a vinyl resin having a basic group described in paragraphs 0150 to 0153 of JP 2019-184763 A, the contents of which are incorporated herein by reference.
  • a resin having an aromatic carboxy group As the resin, it is also preferable to use a resin having an aromatic carboxy group.
  • the aromatic carboxy group may be included in the main chain of a repeating unit, or may be included in a side chain of the repeating unit. It is preferable that the aromatic carboxy group is included in the main chain of a 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 an aromatic ring is preferably 1 to 4, and more preferably 1 to 2.
  • resins having an aromatic carboxy group include the resins described in paragraphs 0082 to 0107 of WO 2021/166858.
  • graft polymers include the resins described in paragraphs 0025 to 0094 of JP2012-255128A, paragraphs 0022 to 0097 of JP2009-203462A, and paragraphs 0102 to 0166 of JP2012-255128A.
  • Star polymers include resins with a structure in which multiple polymer chains are bonded to a core.
  • Specific examples of star polymers include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP2013-043962A.
  • the block copolymer is preferably a block copolymer of a block of a polymer having a repeating unit containing an acid group or a basic group (hereinafter also referred to as block A) and a block of a polymer having a repeating unit not containing an acid group or a basic group (hereinafter also referred to as block B).
  • block copolymer (B) described in paragraphs 0063 to 0112 of JP 2014-219665 A and block copolymer A1 described in paragraphs 0046 to 0076 of JP 2018-156021 A can also be used, the contents of which are incorporated herein by reference.
  • 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 is greater than the amount of acid groups when the total amount of the acid groups and the basic groups is 100 mol%.
  • the basic group possessed by the basic dispersant is preferably an amino group.
  • ester-based solvents substituted with a cyclic alkyl group and ketone-based 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, 2-pentanone, 3-pentanone, 4-heptanone, cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, cycloheptanone, cyclooctanone, cyclohexyl acetate, cyclopentanone, ethyl carbitol acetate, butyl carbitol
  • the amount of aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) used as organic solvents for environmental reasons, etc. (for example, the amount can be 50 ppm (parts per million) by mass or less, 10 ppm by mass or less, or 1 ppm by mass or less, relative to the total amount of organic solvents).
  • the organic solvent may contain isomers (compounds with the same number of atoms but different structures).
  • the organic solvent may contain only one type of isomer, or multiple types of isomers.
  • the peroxide content in the organic solvent is preferably 0.8 mmol/L or less, and more preferably substantially free of peroxide.
  • the content of the solvent in the curable composition is preferably 10 to 95% by mass, more preferably 20 to 90% by mass, and even more preferably 30 to 90% by mass.
  • a method for reducing the environmentally regulated substances a method of reducing the environmentally regulated substances by heating or reducing the pressure in the system to a temperature above the boiling point of the environmentally regulated substances and distilling off the environmentally regulated substances from the system can be mentioned.
  • a polymerization inhibitor or the like may be added and then distilled off under reduced pressure in order to suppress the radical polymerization reaction from proceeding during distillation under reduced pressure and causing crosslinking between molecules.
  • distillation methods can be used at any stage, such as the stage of the raw materials, the stage of the product obtained by reacting the raw materials (for example, a resin solution or a polyfunctional monomer solution after polymerization), or the stage of the curable composition prepared by mixing these compounds.
  • the curable composition of the present invention may also contain a polyalkyleneimine.
  • the polyalkyleneimine is used, for example, as a dispersing aid for pigments.
  • the dispersing aid is a material for enhancing the dispersibility of coloring materials such as pigments in the curable composition.
  • the polyalkyleneimine is a polymer obtained by ring-opening polymerization of an alkyleneimine.
  • the polyalkyleneimine is preferably a polymer having a branched structure containing a primary amino group, a secondary amino group, and a tertiary amino group.
  • the number of carbon atoms in the alkyleneimine is preferably 2 to 6, more preferably 2 to 4, even more preferably 2 or 3, and particularly preferably 2.
  • the number average molecular weight value measured by the viscosity method is used.
  • the number average molecular weight value measured in polystyrene equivalent value by GPC (gel permeation chromatography) method is used.
  • the amine value of the polyalkyleneimine is preferably 5 mmol/g or more, more preferably 10 mmol/g or more, and even more preferably 15 mmol/g or more.
  • alkyleneimines include ethyleneimine, propyleneimine, 1,2-butyleneimine, and 2,3-butyleneimine, with ethyleneimine or propyleneimine being preferred, and ethyleneimine being more preferred.
  • the polyalkyleneimine is particularly preferably polyethyleneimine.
  • the polyethyleneimine preferably contains primary amino groups in an amount of 10 mol% or more, more preferably 20 mol% or more, and even more preferably 30 mol% or more, based on the total of the primary amino groups, secondary amino groups, and tertiary amino groups.
  • Commercially available polyethyleneimines include Epomin SP-003, SP-006, SP-012, SP-018, SP-200, and P-1000 (all manufactured by Nippon Shokubai Co., Ltd.).
  • the content of polyalkyleneimine in the total solid content of the curable composition is preferably 0.1 to 5 mass%.
  • the lower limit is preferably 0.2 mass% or more, more preferably 0.5 mass% or more, and even more preferably 1 mass% or more.
  • the upper limit is preferably 4.5 mass% or less, more preferably 4 mass% or less, and even more preferably 3 mass% or less.
  • the content of polyalkyleneimine is preferably 0.5 to 20 mass parts per 100 mass parts of pigment.
  • the lower limit is preferably 0.6 mass% or more, more preferably 1 mass% or more, and even more preferably 2 mass% or more.
  • the upper limit is preferably 10 mass% or less, and even more preferably 8 mass% or less. Only one type of polyalkyleneimine may be used, or two or more types may be used. When two or more types are used, the total amount is preferably within the above range.
  • the curable composition of the present invention may contain a thermal crosslinking agent as a component other than the resin and polymerizable compound described above.
  • the thermal crosslinking agent include a compound having a cyclic ether group.
  • the cyclic ether group include an epoxy group and an oxetanyl group.
  • the epoxy group may be an alicyclic epoxy group.
  • 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 compound having a cyclic ether group is preferably a compound having an epoxy group (hereinafter also referred to as an epoxy compound).
  • Examples of the epoxy compound include compounds having one or more epoxy groups in one molecule, and compounds having two or more epoxy groups are preferred.
  • 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 2 or more.
  • the compounds described in paragraphs 0034 to 0036 of JP-A-2013-011869, paragraphs 0147 to 0156 of JP-A-2014-043556, and paragraphs 0085 to 0092 of JP-A-2014-089408, and the compounds described in JP-A-2017-179172 can also be used.
  • the compound having a cyclic ether group may be a low molecular weight compound (e.g., a molecular weight of less than 2000, or even less than 1000) or a high molecular weight compound (macromolecule) (e.g., a molecular weight of 1000 or more, or in the case of a polymer, a weight average molecular weight of 1000 or more).
  • the weight average molecular weight of the compound having a cyclic ether 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 Marproof G-0150M, G-0105SA, G-0130SP, G-0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, and G-01758 (all manufactured by NOF Corporation, epoxy group-containing polymers).
  • the compounds described in the examples below can also be used as compounds having a cyclic ether group.
  • the content of the thermal crosslinking agent in the total solid content of the curable composition is preferably 0.1 to 20 mass%.
  • the lower limit is, for example, more preferably 0.5 mass% or more, and even more preferably 1 mass% or more.
  • the upper limit is, for example, more preferably 15 mass% or less, and even more preferably 10 mass% or less. Only one type of thermal crosslinking agent may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is within the above range.
  • the curable composition of the present invention may contain an ultraviolet absorber.
  • ultraviolet absorbers include conjugated diene compounds, aminodiene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indole compounds, triazine compounds, and dibenzoyl compounds. Specific examples of such compounds include the compounds described in paragraph 0179 of International Publication No. 2022/085485, the reactive triazine ultraviolet absorbers described in JP-A-2021-178918, the ultraviolet absorbers described in JP-A-2022-007884, the compounds described in Korean Patent Publication No.
  • the content of the ultraviolet absorber in the total solid content of the curable composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass.
  • the ultraviolet absorbing agent may be used alone or in combination with two or more kinds. When two or more kinds are used, it is preferable that the total amount is in the above range.
  • the curable composition of the present invention may contain a polymerization inhibitor.
  • the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis(3-methyl-6-tert-butylphenol), 2,2'-methylenebis(4-methyl-6-t-butylphenol), and N-nitrosophenylhydroxyamine salt (ammonium salt, cerous salt, etc.).
  • p-methoxyphenol is preferred.
  • the content of the polymerization inhibitor in the total solid content of the curable composition is preferably 0.0001 to 5% by mass.
  • the polymerization inhibitor may be one type or two or more types. In the case of two or more types, the total amount is preferably within the above range.
  • the curable composition of the present invention may contain a silane coupling agent.
  • the silane coupling agent include silane compounds having a hydrolyzable group, and it is preferable that the silane coupling agent is a silane compound having a hydrolyzable group and other functional groups.
  • the hydrolyzable group refers to a substituent that is directly bonded to a silicon atom and can generate a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction.
  • Examples of the hydrolyzable group include a halogen atom, an alkoxy group, and an acyloxy group, and an alkoxy group is preferable.
  • the silane coupling agent is preferably a compound having an alkoxysilyl group.
  • functional groups other than the hydrolyzable group include a vinyl group, a (meth)allyl group, a (meth)acryloyl group, a mercapto group, an epoxy group, an oxetanyl group, an amino group, a ureido group, a sulfide group, an isocyanate group, and a phenyl group, and an amino group, a (meth)acryloyl group, and an epoxy group are preferable.
  • Specific examples of the silane coupling agent include the compounds described in paragraph 0177 of International Publication No.
  • the content of the silane coupling agent in the total solid content of the curable composition is preferably 0.01 to 15.0% by mass, more preferably 0.05 to 10.0% by mass.
  • the silane coupling agent may be one type or two or more types. In the case of two or more types, it is preferable that the total amount is within the above range.
  • the curable composition of the present invention may contain a surfactant.
  • a surfactant various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone-based surfactant may be used.
  • the surfactant is preferably a silicone-based surfactant or a fluorine-based surfactant, and more preferably a silicone-based surfactant.
  • Nonionic surfactants include the compounds described in paragraph 0174 of WO 2022/085485.
  • Silicone surfactants include DOWSIL SH8400, SH8400 FLUID, FZ-2122, 67 Additive, 74 Additive, M Additive, and SF 8419.
  • OIL all manufactured by Dow Toray Co., Ltd.
  • TSF-4300, TSF-4445, TSF-4460, TSF-4452 all manufactured by Momentive Performance Materials, Inc.
  • KP-341, KF-6000, KF-6001, KF-6002, KF-6003 all manufactured by Shin-Etsu Chemical Co., Ltd.
  • BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-3760, BYK-UV3510 all manufactured by BYK-Chemie
  • As the silicone surfactant a compound having the following structure can also be used.
  • the content of the surfactant in the total solid content of the curable composition is preferably 0.001% by mass to 5.0% by mass, and more preferably 0.005% by mass to 3.0% by mass.
  • the surfactant may be one type or two or more types. When two or more types are used, it is preferable that the total amount is within the above range.
  • the curable composition of the present invention may contain an antioxidant.
  • the antioxidant include phenolic compounds, phosphite compounds, and thioether compounds.
  • the phenolic compound any phenolic compound known as a phenolic antioxidant may be used.
  • a preferred phenolic compound is a hindered phenolic compound.
  • a compound having a substituent at the site (ortho position) adjacent to the phenolic hydroxy group is preferred.
  • a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferred.
  • the antioxidant is also preferably a compound having a phenolic group and a phosphite ester group in the same molecule.
  • a phosphorus-based antioxidant may also be suitably used as the antioxidant.
  • phosphorus-based antioxidants include tris[2-[[2,4,8,10-tetrakis(1,1-dimethylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl]oxy]ethyl]amine, tris[2-[(4,6,9,11-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphepin-2-yl)oxy]ethyl]amine, and ethylbis(2,4-di-tert-butyl-6-methylphenyl)phosphite.
  • antioxidants include, for example, Adeka STAB AO-20, Adeka STAB AO-30, Adeka STAB AO-40, Adeka STAB AO-50, Adeka STAB AO-50F, Adeka STAB AO-60, Adeka STAB AO-60G, Adeka STAB AO-80, and Adeka STAB AO-330 (manufactured by ADEKA Corporation).
  • the antioxidant may be a compound described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, a compound described in International Publication No. WO 2017/006600, a compound described in International Publication No. WO 2017/164024, or a compound described in Korean Patent Publication No. 10-2019-0059371.
  • the content of the antioxidant in the total solid content of the curable composition is preferably 0.01 to 20 mass%, more preferably 0.3 to 15 mass%. Only one type of antioxidant may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount is in the above range.
  • the curable composition of the present invention may contain, as necessary, a sensitizer, a plasticizer, and other auxiliaries (e.g., conductive particles, fillers, defoamers, flame retardants, leveling agents, peeling promoters, fragrances, surface tension regulators, chain transfer agents, etc.).
  • auxiliaries e.g., conductive particles, fillers, defoamers, flame retardants, leveling agents, peeling promoters, fragrances, surface tension regulators, chain transfer agents, etc.
  • properties such as film properties can be adjusted.
  • the compounds described in paragraph 0182 of WO 2022/085485 can be used.
  • the thiol compound described in JP 2020-109068 A can be used as the chain transfer agent.
  • the curable composition of the present invention may contain a metal oxide in order to adjust the refractive index of the resulting film.
  • the metal oxide include TiO 2 , ZrO 2 , Al 2 O 3 , and SiO 2.
  • the primary particle size of the metal oxide is preferably 1 to 100 nm, more preferably 3 to 70 nm, and even more preferably 5 to 50 nm.
  • the metal oxide may have a core-shell structure. In this case, the core may be hollow.
  • the curable composition of the present invention may contain a light resistance improver.
  • the light resistance improver include the compounds described in paragraph 0183 of WO 2022/085485.
  • the curable composition of the present invention is substantially free of terephthalic acid esters.
  • substantially free means that the content of terephthalic acid esters in the total amount of the curable composition is 1000 ppb by mass or less, more preferably 100 ppb by mass or less, and particularly preferably zero.
  • the curable composition of the present invention has a melamine content of 10,000 ppm by mass or less.
  • the curable composition of the present invention preferably has a free metal content of 100 ppm or less, more preferably 50 ppm or less.
  • the free halogen content is preferably 100 ppm or less, more preferably 50 ppm or less.
  • Methods for reducing free metals and halogens in the curable composition include washing with ion-exchanged water, filtration, ultrafiltration, and purification with ion-exchange resins.
  • perfluoroalkylsulfonic acid and its salts may be restricted.
  • the content of perfluoroalkylsulfonic acid (particularly perfluoroalkylsulfonic acid having 6 to 8 carbon atoms in the perfluoroalkyl group) and its salts, and perfluoroalkylcarboxylic acid (particularly perfluoroalkylcarboxylic acid having 6 to 8 carbon atoms in the perfluoroalkyl group) and its salts is preferably in the range of 0.01 ppb to 1,000 ppb, more preferably in the range of 0.05 ppb to 500 ppb, and even more preferably in the range of 0.1 ppb to 300 ppb, based on the total solid content of the curable composition.
  • the curable composition of the present invention may be substantially free of perfluoroalkylsulfonic acid and its salts, and perfluoroalkylcarboxylic acid and its salts.
  • a curable composition that is substantially free of perfluoroalkylsulfonic acid and its salt, and perfluoroalkyl carboxylic acid and its salt may be selected.
  • Examples of compounds that can be a substitute for regulated compounds include compounds that are excluded from the scope of regulation due to the difference in the number of carbon atoms in the perfluoroalkyl group. However, the above content does not prevent the use of perfluoroalkylsulfonic acid and its salt, and perfluoroalkyl carboxylic acid and its salt.
  • the curable composition of the present invention may contain perfluoroalkylsulfonic acid and its salt, and perfluoroalkyl carboxylic acid and its salt within the maximum allowable range.
  • fluorine-containing compounds may be restricted from the perspective of environmental regulations.
  • the content of fluorine-containing compounds in the curable composition is preferably 5% by mass or less, more preferably 1% by mass or less, and even more preferably 0.1% by mass or less.
  • the curable composition may be substantially free of fluorine-containing compounds.
  • the water content of the curable composition of the present invention is usually 3% by mass or less, preferably 0.01 to 1.5% by mass, and more preferably in the range of 0.1 to 1.0% by mass.
  • the water content can be measured by the Karl Fischer method.
  • the curable composition of the present invention can be used by adjusting the viscosity for the purpose of adjusting the film surface state (flatness, etc.) and film thickness.
  • the viscosity value can be selected appropriately as needed, but for example, a value of 0.3 mPa ⁇ s to 50 mPa ⁇ s at 25°C is preferable, and 0.5 mPa ⁇ s to 20 mPa ⁇ s is more preferable.
  • the viscosity can be measured, for example, using a cone-plate type viscometer with the temperature adjusted to 25°C.
  • the curable composition of the present invention can be prepared by mixing the above-mentioned components.
  • all the components may be simultaneously dissolved and/or dispersed in a solvent to prepare the curable composition, or, if necessary, each component may be appropriately prepared as two or more solutions or dispersions, which are mixed at the time of use (at the time of application) to prepare the curable composition.
  • a process for dispersing the pigment when preparing the curable composition, it is preferable to include a process for dispersing the pigment.
  • mechanical forces used to disperse the pigment include compression, squeezing, impact, shear, and cavitation.
  • Specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high-speed impellers, sand grinders, flow jet mixers, high-pressure wet atomization, and ultrasonic dispersion.
  • grinding the pigment in a sand mill (bead mill) it is preferable to use beads with a small diameter and increase the bead packing rate, thereby increasing the grinding efficiency.
  • the process and dispersing machine for dispersing the pigment may be suitably used as described in "Dispersion Technology Encyclopedia, published by Information Technology Co., Ltd., July 15, 2005” or "Dispersion Technology and Industrial Application Practice Focused on Suspension (Solid/Liquid Dispersion System) - Comprehensive Data Collection, published by Management Development Center Publishing Department, October 10, 1978", and in paragraph number 0022 of JP 2015-157893 A.
  • a salt milling process may be performed to refine the particles. For the materials, equipment, processing conditions, etc.
  • the descriptions in, for example, JP 2015-194521 A and JP 2012-046629 A may be referred to.
  • materials for the beads used for dispersion include zirconia, agate, quartz, titania, tungsten carbide, silicon nitride, alumina, stainless steel, and glass.
  • the beads may also be made of an inorganic compound with a Mohs hardness of 2 or more.
  • the curable composition may contain 1 to 10,000 ppm of the beads.
  • the curable composition When preparing the curable composition, it is preferable to filter the curable composition with a filter for the purpose of removing foreign matter and reducing defects.
  • filters and filtration methods used for filtration include the filters and filtration methods described in paragraphs 0196 to 0199 of WO 2022/085485.
  • the film of the present invention is obtained from the above-mentioned curable composition of the present invention.
  • the film of the present invention can be used for optical filters such as color filters, infrared transmission filters, and infrared cut filters.
  • the thickness of the film of the present invention can be adjusted appropriately depending on the purpose.
  • the 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 When the film of the present invention is used as a color filter, the film of the present invention preferably has a green, red, blue, cyan, magenta or yellow hue, more preferably has a green, red or blue hue, and even more preferably has a green or red hue.
  • the film of the present invention can also 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, and green, red or blue pixels are preferred, and green or red pixels are more preferred.
  • the film of the present invention can be produced through a step of applying the curable composition of the present invention.
  • the film production method preferably further includes a step of forming a pattern (pixel).
  • the method for forming the pattern (pixel) is preferably a photolithography method.
  • Pattern formation by photolithography preferably includes a step of forming a composition layer on a support using the curable composition of the present invention, a step of exposing the composition layer to light in a pattern, and a step of developing and removing the unexposed parts of the composition layer to form a pattern (pixels). If necessary, a step of baking the composition layer (pre-baking step) and a step of baking the developed pattern (pixels) (post-baking step) may be provided.
  • the curable composition of the present invention is used to form a composition layer on a support.
  • the support is not particularly limited and can be appropriately selected depending on the application.
  • a glass substrate, a silicon substrate, etc. can 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.
  • a base layer may be provided on the silicon substrate to improve adhesion with the upper layer, prevent diffusion of substances, or flatten the substrate surface.
  • the surface contact angle of the base layer is preferably 20 to 70° when measured with diiodomethane. It is also preferable that the surface contact angle is 30 to 80° when measured with water.
  • a known method can be used as a method for applying the curable composition.
  • a dropping method drop casting
  • a slit coating method for example, a spray method; a roll coating method; a rotary coating method (spin coating); a casting coating method; a slit and spin method; a pre-wetting method (for example, a method described in JP 2009-145395 A); various printing methods such as inkjet (for example, on-demand method, piezo method, thermal method), ejection printing such as nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, and metal mask printing; a transfer method using a mold or the like; and a nanoimprint method.
  • the application method described in paragraph 0207 of WO 2022/085485 can also be used.
  • the composition layer formed on the support may be dried (prebaked).
  • prebaking may not be performed.
  • the prebaking temperature is preferably 150°C or less, more preferably 120°C or less, and even more preferably 110°C or less.
  • the lower limit can be, for example, 50°C or more, and can also be 80°C or more.
  • the prebaking time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, and even more preferably 80 to 220 seconds. Prebaking can be performed using a hot plate, an oven, etc.
  • the composition layer is exposed to light in a pattern (exposure step).
  • the composition layer can be exposed to light in a pattern by using a stepper exposure machine or a scanner exposure machine through a mask having a predetermined mask pattern. This allows the exposed parts to harden.
  • Radiation (light) that can be used for exposure includes g-line and i-line.
  • 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 line (wavelength 248 nm) and ArF line (wavelength 193 nm), with KrF line (wavelength 248 nm) being preferred.
  • Long-wavelength light sources of 300 nm or more can also be used.
  • Pulse exposure is an exposure method in which light is applied and paused repeatedly in short cycles (e.g., milliseconds 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 performed under air, for example, exposure may be performed under a low-oxygen atmosphere with an oxygen concentration of 19 volume% or less (e.g., 15 volume%, 5 volume%, or substantially oxygen-free), or exposure may be performed under a high-oxygen atmosphere with an oxygen concentration of more than 21 volume% (e.g., 22 volume%, 30 volume%, or 50 volume%).
  • the exposure illuminance can be appropriately set, and can usually be selected from the range of 1000 W/m 2 to 100,000 W/m 2 (e.g., 5,000 W/m 2 , 15,000 W/m 2 , or 35,000 W/m 2 ).
  • the oxygen concentration and exposure illuminance may be appropriately combined.
  • the oxygen concentration can be 10% by volume and the illuminance can be 10,000 W/m 2
  • the oxygen concentration can be 35% by volume and the illuminance can be 20,000 W/m 2 .
  • the unexposed parts of the composition layer are developed and removed to form a pattern (pixels).
  • the unexposed parts of the composition layer can be developed and removed using a developer.
  • the composition layer in the unexposed parts during the exposure process dissolves into the developer, leaving only the photocured parts.
  • the temperature of the developer is preferably, for example, 20 to 30°C.
  • the development time is preferably 20 to 180 seconds. In order to improve residue removal, the process of shaking off the developer every 60 seconds and then supplying new developer may be repeated several times.
  • the developer may be an organic solvent or an alkaline developer, with an alkaline developer being preferred.
  • the developer and the washing (rinsing) method after development may be as described in paragraph 0214 of WO 2022/085485.
  • Additional exposure processing and post-baking are curing processing after development to complete curing.
  • the heating temperature in post-baking is, for example, preferably 100 to 300°C, more preferably 200 to 270°C.
  • Post-baking can be performed continuously or batchwise using a heating means such as a hot plate, a convection oven (hot air circulation dryer), or a high-frequency heater to achieve the above conditions for the developed film.
  • a heating means such as a hot plate, a convection oven (hot air circulation dryer), or a high-frequency heater to achieve the above conditions for the developed film.
  • the light used for exposure has a wavelength of 400 nm or less.
  • additional exposure processing may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
  • the optical filter of the present invention has the above-mentioned film of the present invention.
  • the types of optical filters include color filters, infrared cut filters, and infrared transmission filters, and are preferably color filters.
  • the color filter preferably has the film of the present invention as its pixel, more preferably has the film of the present invention as its color pixel, and even more preferably has the film of the present invention as its red pixel.
  • the optical filter may have a protective layer on the surface of the film of the present invention.
  • a protective layer By providing a protective layer, various functions such as oxygen blocking, low reflection, hydrophilicity/hydrophobicity, and shielding of light of a specific wavelength (ultraviolet rays, 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.
  • Methods for forming the protective layer include a method of forming the protective layer by applying a resin composition for forming the protective layer, a chemical vapor deposition method, and a method of attaching a molded resin with an adhesive.
  • the 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 resin, polyacrylonitrile resin, cellulose resin, Si, C, W, Al 2 O 3 , Mo, SiO 2 , and Si 2 N 4 , and may contain two or more of these components.
  • the protective layer in the case of a protective layer intended for oxygen blocking, preferably contains a polyol resin, SiO 2 , and Si 2 N 4.
  • the protective layer in the case of a protective layer intended for low reflection, preferably contains a (meth)acrylic resin and a fluorine resin.
  • a protective layer by applying a resin composition When forming a protective layer by applying a resin composition, known methods such as spin coating, casting, screen printing, and inkjet can be used as a method for applying the resin composition.
  • Known organic solvents e.g., propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.
  • thermal chemical vapor deposition, plasma chemical vapor deposition, photochemical vapor deposition can be used as the chemical vapor deposition method.
  • the protective layer may contain additives such as organic or inorganic fine particles, absorbents for light of specific wavelengths (e.g., ultraviolet light, infrared light, etc.), refractive index adjusters, antioxidants, adhesion agents, and surfactants, as necessary.
  • organic or 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, and barium sulfate.
  • Known absorbents can be used as absorbents for light of specific wavelengths.
  • the content of these additives can be adjusted as appropriate, but is preferably 0.1 to 70% by mass, and more preferably 1 to 60% by mass, based on the total mass of the protective layer.
  • the protective layer may be the one described in paragraphs 0073 to 0092 of JP2017-151176A.
  • the optical filter may have a structure in which each pixel is embedded in a space partitioned by partitions, for example in a grid pattern.
  • the solid-state imaging device of the present invention has the above-mentioned film of the present invention.
  • the configuration of the solid-state imaging device is not particularly limited as long as it has the film of the present invention and functions as a solid-state imaging device, and examples thereof include the following configurations.
  • the substrate has a plurality of photodiodes constituting the light receiving area of a solid-state imaging element (such as a CCD (charge-coupled device) image sensor or a CMOS (complementary metal-oxide semiconductor) image sensor) and a transfer electrode made of polysilicon or the like, a light-shielding film that opens only the light receiving portion of the photodiode on the photodiode and the transfer electrode, a device protection film made of silicon nitride or the like formed on the light-shielding film so as to cover the entire light-shielding film and the light receiving portion of the photodiode, and a color filter on the device protection film.
  • a solid-state imaging element such as a CCD (charge-coupled device) image sensor or a CMOS (complementary metal-oxide semiconductor) image sensor
  • a transfer electrode made of polysilicon or the like
  • a light-shielding film that opens only the light receiving portion of the photodio
  • the device protection film may have a light-collecting means (e.g., a microlens, etc.; the same applies below) on the device protection film and below the color filter (the side closer to the substrate), or a light-collecting means on the color filter.
  • the color filter may have a structure in which each colored pixel is embedded in a space partitioned by partitions, for example in a lattice shape. In this case, it is preferable that the partitions have a lower refractive index than each colored pixel. Examples of imaging devices having such a structure include those described in JP 2012-227478 A, JP 2014-179577 A, and WO 2018/043654 A.
  • an ultraviolet absorbing layer may be provided in the structure of the solid-state imaging element to improve light resistance.
  • the imaging device equipped with the solid-state imaging element of the present invention can be used for digital cameras, electronic devices with imaging functions (such as mobile phones), as well as in-vehicle cameras and surveillance cameras.
  • the image display device of the present invention has the above-mentioned film of the present invention.
  • Examples of the image display device include liquid crystal display devices and organic electroluminescence display devices.
  • the definition of the image display device and details of each image display device are described, for example, in "Electronic Display Devices” (written by Akio Sasaki, published by Kogyo Chosakai Co., Ltd. in 1990) and “Display Devices” (written by Junsho Ibuki, published by Sangyo Tosho Co., Ltd. in 1989).
  • the liquid crystal display device is described, for example, in “Next Generation Liquid Crystal Display Technology” (edited by Tatsuo Uchida, published by Kogyo Chosakai Co., Ltd. in 1994).
  • There is no particular limitation on the liquid crystal display device to which the present invention can be applied and the present invention can be applied to various types of liquid crystal display devices described in the above "Next Generation Liquid Crystal Display Technology".
  • Compounds P-1 to P-16 and CP-1 used in the examples and comparative examples have the structures shown below.
  • the pKa, weight average molecular weight (Mw), average particle size (nm), and viscosity (cP) of each compound are shown in the table below.
  • the pKa of each compound was measured by neutralization titration with sodium hydroxide.
  • the average particle size (nm) of the pigment in each pigment dispersion was measured by dynamic light scattering using nanoSAQLA (manufactured by Otsuka Electronics Co., Ltd.).
  • the viscosity (mPa ⁇ s) of the pigment in each pigment dispersion was measured using "RE-85L” manufactured by Toki Sangyo Co., Ltd.
  • the viscosity of the pigment dispersion was measured by adjusting the temperature of the pigment dispersion to 25°C.
  • Pigment Green 58 green pigment, phthalocyanine pigment
  • PB15:6 C.I. Pigment Blue 15:6 (blue pigment, phthalocyanine pigment)
  • PV23 C.I. Pigment Violet 23 (purple pigment, dioxazine pigment)
  • PBk32 C.I. Pigment Black 32 (perylene compound, organic black pigment)
  • IR1 Compound having the following structure (near infrared absorbing pigment)
  • solvent 1 Propylene glycol monomethyl ether acetate (PGMEA)
  • solvent 2 Propylene glycol monomethyl ether (PGME)
  • Each curable composition was produced by mixing 566.43 parts by mass of the pigment dispersion shown in the table below, 10.7 parts by mass of the monomer shown in the table below, 33.34 parts by mass of the resin shown in the table below, 5 parts by mass of the photopolymerization initiator shown in the table below, 0.1 parts by mass of the surfactant shown in the table below, 1 part by mass of the heat curing agent shown in the table below, 200 parts by mass of propylene glycol monomethyl ether acetate, 100 parts by mass of cyclopentanone, and 21.96 parts by mass of 1-methoxy-2-propanol, and filtering the mixture through a nylon filter having a pore size of 0.45 ⁇ m (manufactured by Nippon Pall Co., Ltd.).
  • Pigment dispersions G1 to G16, R1 to R16, B1 to B16, IR1 to IR6, Bk1 to Bk6, CG1, CR1, and CB1 the above-mentioned pigment dispersions G1 to G16, R1 to R16, B1 to B16, IR1 to IR6, Bk1 to Bk6, CG1, CR1, and CB1
  • M-1 KAYARAD DPHA (a mixture of dipentaerythritol pentaacrylate and dipentaerythritol hexaacrylate, manufactured by Nippon Kayaku Co., Ltd.)
  • M-2 NK Ester A-DPH-12E (ethylene oxide (EO) modified hexafunctional acrylate compound, manufactured by Shin-Nakamura Chemical Co., Ltd.)
  • M-3 NK Ester A-TMMT (pentaerythritol tetraacrylate, manufactured by Shin-Nakamura Chemical Co., Ltd.)
  • B-1 Resin having the following structure (the number attached to the main chain is the molar ratio, and the number attached to the side chain is the number of repeating units. Weight average molecular weight: 21,000)
  • B-2 Resin having the following structure (the number attached to the main chain is the molar ratio, and the number attached to the side chain is the number of repeating units. Weight average molecular weight: 18,000)
  • B-3 Resin having the following structure (the number added to the main chain is the molar ratio of the repeating unit. Weight average molecular weight: 11,000)
  • T-1 to T-3 Compounds having the following structures
  • a composition for forming an undercoat layer (CT-4000L, manufactured by Fujifilm Electronic Materials Co., Ltd.) was applied to an 8-inch (20.32 cm) silicon wafer using a spin coater so that the thickness after post-baking was 0.1 ⁇ m, and the wafer was heated at 220° C. for 300 seconds using a hot plate to form an undercoat layer, thereby obtaining a silicon wafer (support) with an undercoat layer.
  • each curable composition was applied by spin coating so that the film thickness after post-baking was 0.5 ⁇ m.
  • the wafer was heated at 90° C. for 2 minutes using a hot plate.
  • a composition for forming an undercoat layer (CT-4000L, manufactured by Fujifilm Electronic Materials Co., Ltd.) was applied to an 8-inch (20.32 cm) silicon wafer using a spin coater so that the thickness after post-baking was 0.1 ⁇ m, and the wafer was heated at 220° C. for 300 seconds using a hot plate to form an undercoat layer, thereby obtaining a silicon wafer (support) with an undercoat layer.
  • each curable composition was applied by spin coating so that the film thickness after post-baking was 0.5 ⁇ m.
  • the wafer was heated at 100° C. for 2 minutes using a hot plate.
  • the wafer was exposed to light having a wavelength of 365 nm at a specific exposure amount through a mask of a Bayer pattern of 1.0 ⁇ m square using an i-line stepper exposure device FPA-3000i5+ (manufactured by Canon Inc.).
  • the composition layer after exposure was developed using a development device (Act8 manufactured by Tokyo Electron Co., Ltd.).
  • a 0.15% by mass aqueous solution of tetramethylammonium hydroxide (TMAH) was used as the developer, and shower development was performed at 23° C. for 60 seconds. After that, rinsing was performed with a spin shower using pure water, and then spin drying was performed.
  • TMAH tetramethylammonium hydroxide
  • a heat treatment (post-baking) was performed for 5 minutes using a hot plate at 200° C. to form a pattern (pixel).
  • the silicon wafer on which the pixels were formed was divided, platinum was evaporated, and a cross-sectional scanning electron microscope (SEM) image of the pattern was obtained using a scanning electron microscope (manufactured by Hitachi High-Tech Corporation).
  • SEM scanning electron microscope
  • the obtained pattern was observed while changing the specific exposure dose, and the minimum exposure dose at which a square pattern with a side length of 1.0 ⁇ m was resolved was determined, and the sensitivity was evaluated according to the following evaluation criteria.
  • the smaller the minimum exposure dose the better the sensitivity of the composition.
  • -Evaluation criteria- 5 The minimum exposure amount was less than 100 mJ/cm2 .
  • the minimum exposure amount was 100 mJ/ cm2 or more and less than 200 mJ/ cm2.
  • 3 The minimum exposure amount was 200 mJ/ cm2 or more and less than 500 mJ/ cm2.
  • 2 The minimum exposure amount was 500 mJ/ cm2 or more and less than 1000 mJ/ cm2.
  • 1 The minimum exposure amount was 1000 mJ/ cm2 or more.
  • the curable compositions of the examples had excellent storage stability and developability. In addition, the curable compositions of the examples had excellent sensitivity.
  • the films obtained from the curable compositions described in the examples can be suitably used in optical filters, solid-state imaging devices, and image display devices.

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Abstract

L'invention concerne une composition durcissable comprenant un colorant comportant un pigment, un composé polymérisable, un initiateur de photopolymérisation et un composé représenté par la formule (1). L'invention concerne également un film, un filtre optique, un élément d'imagerie à semi-conducteurs et un dispositif d'affichage d'image qui sont obtenus à l'aide de la composition.
PCT/JP2024/028609 2023-08-23 2024-08-09 Composition durcissable, film, filtre optique, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image Pending WO2025041643A1 (fr)

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JP2023135540 2023-08-23
JP2023-135540 2023-08-23

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Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012086213A1 (fr) * 2010-12-22 2012-06-28 第一工業製薬株式会社 Agent dispersant et composition de dispersion
WO2013077219A1 (fr) * 2011-11-25 2013-05-30 第一工業製薬株式会社 Composition de résine pour un matériau optique
JP2016147261A (ja) * 2015-02-06 2016-08-18 日油株式会社 非水系分散剤および非水系分散体組成物
WO2016136580A1 (fr) * 2015-02-24 2016-09-01 第一工業製薬株式会社 Composition de dispersion et son produit durci, et stratifié
WO2021039410A1 (fr) * 2019-08-27 2021-03-04 富士フイルム株式会社 Composition pouvant durcir, produit durci, filtre coloré, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image
WO2021161939A1 (fr) * 2020-02-14 2021-08-19 富士フイルム株式会社 Composition photosensible, procédé de formation de pixel, procédé de production de filtre optique, procédé de production d'élément d'imagerie à semi-conducteurs et procédé de production de dispositif d'affichage d'image
JP2022506036A (ja) * 2018-10-30 2022-01-17 クローダ，インコーポレイティド 微細粒子を水性又は極性の溶媒中に分散させる方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012086213A1 (fr) * 2010-12-22 2012-06-28 第一工業製薬株式会社 Agent dispersant et composition de dispersion
WO2013077219A1 (fr) * 2011-11-25 2013-05-30 第一工業製薬株式会社 Composition de résine pour un matériau optique
JP2016147261A (ja) * 2015-02-06 2016-08-18 日油株式会社 非水系分散剤および非水系分散体組成物
WO2016136580A1 (fr) * 2015-02-24 2016-09-01 第一工業製薬株式会社 Composition de dispersion et son produit durci, et stratifié
JP2022506036A (ja) * 2018-10-30 2022-01-17 クローダ，インコーポレイティド 微細粒子を水性又は極性の溶媒中に分散させる方法
WO2021039410A1 (fr) * 2019-08-27 2021-03-04 富士フイルム株式会社 Composition pouvant durcir, produit durci, filtre coloré, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image
WO2021161939A1 (fr) * 2020-02-14 2021-08-19 富士フイルム株式会社 Composition photosensible, procédé de formation de pixel, procédé de production de filtre optique, procédé de production d'élément d'imagerie à semi-conducteurs et procédé de production de dispositif d'affichage d'image

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