WO2021157501A1 - 着色組成物、膜、光学フィルタ、固体撮像素子及び画像表示装置 - Google Patents
着色組成物、膜、光学フィルタ、固体撮像素子及び画像表示装置 Download PDFInfo
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- WO2021157501A1 WO2021157501A1 PCT/JP2021/003442 JP2021003442W WO2021157501A1 WO 2021157501 A1 WO2021157501 A1 WO 2021157501A1 JP 2021003442 W JP2021003442 W JP 2021003442W WO 2021157501 A1 WO2021157501 A1 WO 2021157501A1
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- 125000001246 bromo group Chemical group Br* 0.000 description 1
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- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
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- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
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- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
-
- 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
- C09B25/00—Quinophthalones
-
- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/10—Obtaining compounds having halogen atoms directly bound to the phthalocyanine skeleton
-
- 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
- C09B55/00—Azomethine dyes
-
- 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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/41—Organic pigments; Organic dyes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/208—Filters for use with infrared or ultraviolet radiation, e.g. for separating visible light from infrared and/or ultraviolet radiation
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/14—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation
- H01L27/144—Devices controlled by radiation
- H01L27/146—Imager structures
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- H—ELECTRICITY
- H04—ELECTRIC COMMUNICATION TECHNIQUE
- H04N—PICTORIAL COMMUNICATION, e.g. TELEVISION
- H04N25/00—Circuitry of solid-state image sensors [SSIS]; Control thereof
- H04N25/10—Circuitry of solid-state image sensors [SSIS]; Control thereof for transforming different wavelengths into image signals
- H04N25/11—Arrangement of colour filter arrays [CFA]; Filter mosaics
- H04N25/13—Arrangement of colour filter arrays [CFA]; Filter mosaics characterised by the spectral characteristics of the filter elements
- H04N25/131—Arrangement of colour filter arrays [CFA]; Filter mosaics characterised by the spectral characteristics of the filter elements including elements passing infrared wavelengths
Definitions
- the present invention relates to a coloring composition containing a yellow colorant.
- the present invention also relates to a film, an optical filter, a solid-state image sensor, and an image display device using the coloring composition.
- color filters are used as key devices for displays and optical elements.
- a color filter usually includes pixels of the three primary colors of red, green, and blue, and plays a role of decomposing transmitted light into the three primary colors.
- the colored pixels of each color of the color filter are manufactured by using a coloring composition containing a coloring agent.
- a coloring composition for a color filter composed of at least a pigment, a polymer, and a solvent
- the content of the yellow pigment in the pigment component is 30% by weight or more
- the yellow pigment is a quinophthalone-based pigment.
- Isoindrin pigment, Isoindrinone pigment, Nickel azo complex pigment, Metin / azomethine pigment, and the specific surface area of the yellow pigment is 70 m 2 / g or more.
- Inventions relating to the composition are described.
- an object of the present invention is to provide a coloring composition capable of forming a film having excellent long-term reliability. Another object of the present invention is to provide a film, an optical filter, a solid-state image sensor, and an image display device using the coloring composition.
- the present invention provides the following.
- the content of the yellow colorant in the colorant is 30% by mass or more.
- the yellow colorant is a coloring composition containing 15% by mass or more of an azomethine metal complex.
- the coloring composition according to ⁇ 1>, wherein the content of the quinophthalone compound in the yellow colorant is less than 50% by mass.
- ⁇ 3> The coloring composition according to ⁇ 1> or ⁇ 2>, wherein the azomethine metal complex contains at least one selected from an azomethine copper complex and an azomethine zinc complex.
- the coloring agent contains at least one selected from a green coloring agent and a red coloring agent.
- the coloring agent contains a green coloring agent, and the green coloring agent contains a phthalocyanine compound.
- ⁇ 6> When a film having a thickness of 0.65 ⁇ m is formed using the coloring composition, a wavelength at which the light transmittance of the film is 50% exists in the wavelength range of 470 to 520 nm.
- ⁇ 7> The coloring composition according to any one of ⁇ 1> to ⁇ 6>, further comprising a polymerizable compound and a photopolymerization initiator.
- ⁇ 8> The coloring composition according to any one of ⁇ 1> to ⁇ 7>, which is for a color filter or an infrared transmission filter.
- ⁇ 9> A film obtained from the coloring composition according to any one of ⁇ 1> to ⁇ 8>.
- ⁇ 11> A solid-state image sensor having the film according to ⁇ 9>.
- ⁇ 12> An image display device having the film according to ⁇ 9>.
- the present invention it is possible to provide a coloring composition capable of forming a film having excellent long-term reliability. Further, it is possible to provide a film, an optical filter, a solid-state image sensor, and an image display device using the coloring composition.
- the contents of the present invention will be described in detail.
- "-" is used to mean that the numerical values described before and after it are included as the lower limit value and the upper limit value.
- the notation not describing substitution and non-substitution also includes a group having a substituent (atomic group) as well as a group having no substituent (atomic group).
- the "alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
- exposure includes not only exposure using light but also drawing using particle beams such as an electron beam and an ion beam.
- the light used for exposure include the emission line spectrum of a mercury lamp, far ultraviolet rays typified by an excimer laser, extreme ultraviolet rays (EUV light), X-rays, active rays such as electron beams, or radiation.
- EUV light extreme ultraviolet rays
- (meth) acrylate represents both acrylate and methacrylate, or either
- (meth) acrylic represents both acrylic and methacrylic, or either.
- Acryloyl "represents both acryloyl and / or methacryloyl.
- Me in the structural formula 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 the number average molecular weight are polystyrene-equivalent values measured by a GPC (gel permeation chromatography) method.
- the total solid content means the total mass of all the components of the composition excluding the solvent.
- the term pigment means a compound that is difficult to dissolve in a solvent.
- the term "process" is included in this term not only as an independent process but also as long as the desired action of the process is achieved even if it cannot be clearly distinguished from other processes. ..
- the coloring composition of the present invention A coloring composition containing a colorant containing a yellow colorant, a resin, and a solvent.
- the content of the yellow colorant in the colorant is 30% by mass or more,
- the yellow colorant is characterized by containing 15% by mass or more of the azomethine metal complex.
- the film obtained by using the coloring composition of the present invention can suppress the movement of the colorant contained in the film to adjacent pixels or the like even when exposed to a high temperature and high humidity environment for a long period of time. It has excellent reliability. Although the detailed reason for obtaining such an effect is unknown, the content of the yellow colorant in the colorant is 30% by mass or more, and the azomethine metal complex is contained in the colorant in an amount of 15% by mass or more. It is presumed that a film with a high film density can be formed by using the above, and as a result, even when the film is exposed to a high temperature and high humidity environment, it is presumed that the expansion of the film can be suppressed. Will be done.
- the azomethine metal complex easily interacts with a colorant other than the azomethine metal complex and a component other than the colorant contained in the film, and the strong interaction between the azomethine metal complex and the component in the film causes the colorant to move. It is presumed that such factors could be suppressed. For this reason, it is presumed that the coloring composition of the present invention was able to form a film having excellent long-term reliability.
- the coloring composition of the present invention is preferably used as a coloring composition for a color filter or an infrared transmission filter. More specifically, it can be preferably used as a coloring composition for forming pixels of a color filter or a coloring composition for forming an infrared transmission filter, and more preferably used as a coloring composition for forming pixels of a color filter.
- the wavelength at which the light transmittance of the film is 50% exists in the wavelength range of 470 to 520 nm, 475 to 725. It is more preferably present in the wavelength range of 520 nm, and even more preferably in the wavelength range of 480 to 520 nm. Among them, it is preferable that the wavelength at which the light transmittance is 50% exists in each of the wavelength range of 470 to 520 nm and the wavelength range of 575 to 625 nm.
- the wavelength on the short wavelength side where the light transmittance is 50% preferably exists in the wavelength range of 475 to 520 nm, and more preferably exists in the wavelength range of 480 to 520 nm. Further, the wavelength on the long wavelength side where the light transmittance is 50% preferably exists in the wavelength range of 580 to 620 nm, and more preferably exists in the wavelength range of 585 to 615 nm.
- a coloring composition capable of forming a film having such spectral characteristics is preferably used as a coloring composition for forming green pixels of a color filter.
- the coloring composition of the present invention contains a coloring agent containing a yellow coloring agent.
- a coloring agent containing an azomethine metal complex is used as the yellow colorant.
- the azomethine metal complex used in the yellow colorant is preferably a pigment because it is easy to form a film having better long-term reliability. That is, the azomethine metal complex used in the yellow colorant is preferably an azomethine metal complex yellow pigment. Further, the azomethine metal complex preferably contains at least one selected from the azomethine copper complex and the azomethine zinc complex because it is easy to form a film having more excellent long-term reliability, and more preferably contains the azomethine copper complex. preferable. Only one type of azomethine metal complex may be used, or two or more types may be used in combination. When two or more kinds of azomethine metal complexes are used in combination, two or more kinds of azomethine metal complexes may form a mixed crystal (solid solution).
- Examples of the azomethine copper complex include Color Index (CI) Pigment Yellow 117, 129 and the like.
- C. I. Pigment Yellow 117 is a compound represented by the following formula (ACu-2)
- C.I. I. Pigment Yellow 129 is a compound represented by the following formula (ACu-1).
- Examples of the azomethine zinc complex include a compound represented by the formula (AZn-1), a compound represented by the formula (AZn-2), and the like.
- X 1 and X 2 independently represent a hydrogen atom, a halogen atom or an alkoxy group, respectively.
- Examples of the halogen atom represented by X 1 and X 2 include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a chlorine atom or a bromine atom is preferable, and a chlorine atom is more preferable.
- Examples of the alkoxy group represented by X 1 and X 2 include a methoxy group, an ethoxy group, a propyloxy group, an i-propyloxy group, a butyloxy group, an i-butyloxy group, an s-butyloxy group, a t-butyloxy group, and a pentyloxy group.
- Specific examples of the compound represented by the formula (AZn-2) include compounds having the following structures.
- the azomethine metal complex it is also preferable to use a mixture or mixed crystal (solid solution) of the compound represented by the formula (ACu-1) and the compound represented by the formula (AZn-1).
- the color value is high, and it is possible to enhance the light-shielding performance at the same content.
- the above mixture or mixed crystal (solid solution) may contain 10 to 900 parts by mass of the compound represented by the formula (AZn-1) with respect to 100 parts by mass of the compound represented by the formula (ACu-1). It is preferably contained in an amount of 25 to 400 parts by mass.
- the colorant used in the coloring composition of the present invention may further contain a yellow colorant other than the azomethine metal complex.
- a yellow colorant other than the azomethine metal complex By further containing a yellow colorant other than the azomethine metal complex, an optical filter having more excellent spectral characteristics can be obtained.
- the yellow colorant other than the azomethine metal complex examples include an azo compound, an isoindoline compound, a pteridine compound, and a quinophthalone compound. It is preferably an indoline compound or a pteridine compound, and more preferably an azo compound or an isoindoline compound.
- the azo compound used as the yellow colorant is preferably an azo metal complex because it is easy to obtain a film having excellent spectral characteristics and light resistance.
- yellow colorant other than the azomethine metal complex examples include C.I. I. Pigment Yellow 1,2,3,4,5,6,10,11,12,13,14,15,16,17,18,20,24,31,32,34,35,35: 1,36, 36: 1,37,37: 1,40,42,43,53,55,60,61,62,63,65,73,74,77,81,83,86,93,94,95,97, 98,100,101,104,106,108,109,110,113,114,115,116,118,119,120,123,125,126,127,128,137,138,139,147,148, 150, 151,152,153,154,155,156,161,162,164,166,167,168,169,170,171,172,173,174,175,176,177,179,180,181 182,185,187,188,193,194,199,213,214,215,228,231,232 (methine type), 233 (quino
- the compounds described in JP-A-2017-201003, the compounds described in JP-A-2017-197719, and paragraph numbers 0011 to 0062 of JP-A-2017-171912 The compounds described in 0137 to 0276, the compounds described in JP-A-2017-171913, paragraphs 0010 to 0062, 0138-0295, and the compounds described in JP-A-2017-171914, paragraph numbers 0011 to 0062, 0139-0190.
- the methine dye described in the above can also be used.
- multimers of these compounds are also preferably used from the viewpoint of improving the color value.
- Examples of the yellow colorant other than the azomethine metal complex include C.I. I. Pigment Yellow 129, 139, 150, 185 is preferred, with C.I. I. Pigment Yellow 150 is more preferred.
- the colorant contained in the coloring composition of the present invention may further contain a colorant having a hue other than the yellow colorant.
- a colorant having another hue to be used in combination include a chromatic colorant such as a green colorant, a red colorant, a purple colorant, a blue colorant, and an orange colorant, and a black colorant.
- the colorant having another hue is preferably at least one selected from a green colorant, a red colorant and an orange colorant, and is preferably at least one selected from a green colorant and a red colorant. More preferred.
- the other colorant may be a pigment or a dye, but is preferably a pigment.
- the colorant contained in the film is transferred to adjacent pixels or the like by the interaction between the pigment as another colorant and the azomethine metal complex which is a yellow colorant.
- a film that can be suppressed more effectively and has excellent long-term reliability can be formed. Such an effect is remarkable when a green pigment is used as another colorant, and the most remarkable effect is particularly exhibited when a phthalocyanine compound is used as the green pigment.
- red colorant examples include diketopyrrolopyrrole compounds, anthraquinone compounds, azo compounds, naphthol compounds, azomethine compounds, xanthene compounds, quinacridone compounds, perylene compounds, and thioindigo compounds, which form films with excellent long-term reliability. It is preferably a diketopyrrolopyrrole compound, an anthraquinone compound, or an azo compound, and more preferably a diketopyrrolopyrrole compound because it is easy to use. Further, the red colorant is preferably a pigment.
- red colorant examples include C.I. I. Pigment Red 1,2,3,4,5,6,7,9,10,14,17,22,23,31,38,41,48: 1,48: 2,48: 3,48: 4, 49,49: 1,49: 2,52: 1,52: 2,53: 1,57: 1,60: 1,63: 1,66,67,81: 1,81: 2,81: 3, 83,88,90,105,112,119,122,123,144,146,149,150,155,166,168,169,170,171,172,175,176,177,178,179,184 185,187,188,190,200,202,206,207,208,209,210,216,220,224,226,242,246,254,255,264,269,270,272,279,291
- red pigments such as 294, 295, 296, and 297.
- red colorant a diketopyrrolopyrrole compound in which at least one bromine atom is substituted in the structure described in JP-A-2017-201384, and diketopyrrolop described in paragraphs 0016 to 0022 of Patent No. 6248838.
- the red colorant described in Japanese Patent No. 6516119, the red colorant described in Japanese Patent No. 6525101, and the like can also be used.
- red colorant a compound having a structure in which an aromatic ring group having an oxygen atom, a sulfur atom or a nitrogen atom bonded to the aromatic ring is bonded to a diketopyrrolopyrrole skeleton is used. You can also.
- C.I. I. Pigment Red 122,177,254,255,264,269,27 preferably C.I. I. Pigment Red 254,264,272 is more preferred, C.I. I. Pigment Red 254,264 is even more preferred.
- the green colorant examples include a phthalocyanine compound and a squarylium compound, and a phthalocyanine compound is preferable because it is easy to form a film having better long-term reliability. Further, the green colorant is preferably a pigment.
- green colorants include C.I. I. Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65, 66 and other green pigments can be mentioned.
- a green colorant a halogenated zinc phthalocyanine having an average of 10 to 14 halogen atoms in one molecule, an average of 8 to 12 bromine atoms, and an average of 2 to 5 chlorine atoms. Pigments can also be used.
- Specific examples include the compounds described in WO 2015/118720.
- C.I. I. Pigment Green 7,36,58,62,63 is preferred, with C.I. I. Pigment greens 36 and 58 are more preferred.
- orange colorant examples include C.I. I. Pigment Orange 2,5,13,16,17: 1,31,34,36,38,43,46,48,49,51,52,55,59,60,61,62,64,71,73, etc.
- purple colorant examples include C.I. I. Pigment Violet 1,19,23,27,32,37,42,60,61 and other purple pigments can be mentioned.
- blue colorant examples include C.I. I. Pigment Blue 1,2,15,15: 1,15: 2,15: 3,15: 4,15: 6,16,22,29,60,64,66,79,80,87,88, etc. Pigments can be mentioned.
- Examples of the black colorant include bisbenzofuranone compounds, azomethine compounds, perylene compounds, azo compounds and the like, and bisbenzofuranone compounds and perylene compounds are preferable.
- Examples of the bisbenzofuranone compound include the compounds described in Japanese Patent Publication No. 2010-534726, Japanese Patent Publication No. 2012-515233, Japanese Patent Publication No. 2012-515234, and the like. It is available.
- Examples of the perylene compound include the compounds described in paragraphs 0016 to 0020 of JP-A-2017-226821, C.I. I. Pigment Black 31, 32 and the like can be mentioned.
- Examples of the azomethine compound include compounds described in JP-A-01-170601 and JP-A-02-0346664, and are available as, for example, "Chromofine Black A1103" manufactured by Dainichiseika.
- the coloring composition of the present invention contains a green coloring agent, it is preferably used as a coloring composition for forming green pixels of a color filter.
- the coloring composition of the present invention contains a red colorant, it is preferably used as a coloring composition for forming red pixels of a color filter.
- the colorant contained in the coloring composition may contain two or more kinds of chromatic colorants, and a combination of two or more kinds of chromatic colorants may form black.
- a coloring composition is preferably used as a coloring composition for forming an infrared transmission filter.
- the following are examples of combinations of chromatic colorants when black is formed by a combination of two or more chromatic colorants.
- An embodiment containing a red colorant, a blue colorant, and a yellow colorant. An embodiment containing a red colorant, a blue colorant, a yellow colorant, and a purple colorant.
- An embodiment containing a red colorant, a blue colorant, a yellow colorant, a purple colorant, and a green colorant An embodiment containing a red colorant, a blue colorant, a yellow colorant, and a green colorant.
- An embodiment containing a red colorant, a blue colorant, a yellow colorant, and a green colorant. An embodiment containing a
- the content of the colorant in the total solid content of the coloring composition is preferably 40% by mass or more, more preferably 50% by mass or more, and further preferably 55% by mass or more.
- the upper limit is preferably 80% by mass or less, more preferably 75% by mass or less, and further preferably 70% by mass or less.
- the content of the yellow colorant in the colorant is 30% by mass or more, preferably 33% by mass or more, and preferably 35% by mass or more, for the reason of improving the color separability from the blue pixel. More preferred.
- the upper limit can be 100% by mass, 95% by mass or less, or 90% by mass or less.
- the content of the azomethine metal complex in the yellow colorant is 15% by mass or more, preferably 15.5% by mass or more, and more preferably 16% by mass or more.
- the upper limit can be 100% by mass, 95% by mass or less, or 90% by mass or less.
- the content of the quinophthalone compound in the yellow colorant is preferably less than 50% by mass, more preferably 40% by mass or less, and further preferably 30% by mass or less from the viewpoint of light resistance. , It is particularly preferable that it is not substantially contained.
- the case where the yellow colorant does not substantially contain the quinophthalone compound means that the content of the quinophthalone compound in the yellow colorant is 0.1% by mass or less, and is 0.05. It is preferably 1% by mass or less, more preferably 0.01% by mass or less, and particularly preferably not containing a quinophthalone compound.
- the content of the azomethine metal complex in the total solid content of the coloring composition is preferably 3% by mass or more, more preferably 5% by mass or more, and further preferably 10% by mass or more.
- the upper limit is preferably 80% by mass or less, more preferably 75% by mass or less, and further preferably 70% by mass or less.
- the coloring composition of the present invention is used as a coloring composition for forming green pixels of a color filter, it is preferable to use a coloring agent containing a yellow coloring agent and a green coloring agent.
- the content of the azomethine metal complex is preferably 3 parts by mass or more, more preferably 5 parts by mass or more, and further preferably 10 parts by mass or more with respect to 100 parts by mass of the green colorant. preferable.
- the content of the azomethine metal complex is preferably 3 parts by mass or more, more preferably 5 parts by mass or more, and further preferably 10 parts by mass or more with respect to 100 parts by mass of the phthalocyanine compound. ..
- the coloring composition of the present invention is used as a coloring composition for forming red pixels of a color filter, it is preferable to use a coloring agent containing a yellow coloring agent and a red coloring agent.
- the content of the azomethine metal complex is preferably 3 parts by mass or more, more preferably 5 parts by mass or more, and further preferably 10 parts by mass or more with respect to 100 parts by mass of the red colorant. preferable.
- the content of the azomethine metal complex is preferably 3 parts by mass or more, more preferably 5 parts by mass or more, and 10 parts by mass or more with respect to 100 parts by mass of the diketopyrrolopyrrole compound. Is more preferable.
- the coloring composition of the present invention contains a resin.
- the resin is blended, for example, for the purpose of dispersing a pigment or the like in a coloring composition or for the purpose of a binder.
- a resin mainly used for dispersing a pigment or the like in a coloring composition is also referred to as a dispersant.
- such an application of the resin is an example, and the resin can be used for purposes other than such an application.
- the weight average molecular weight (Mw) of the resin is preferably 2000 to 2000000.
- the upper limit is preferably 1,000,000 or less, and more preferably 500,000 or less.
- the lower limit is preferably 3000 or more, and more preferably 5000 or more.
- the resin examples include (meth) acrylic resin, epoxy resin, en-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, and polyimide resin.
- examples thereof include polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, and styrene resin. One of these resins may be used alone, or two or more of these resins may be mixed and used.
- the coloring composition of the present invention preferably contains a resin having an acid group.
- the acid group include a carboxyl group, a phosphoric acid group, a sulfo group, and a phenolic hydroxy group. These acid groups may be only one kind or two or more kinds.
- the resin having an acid group can also be used as a dispersant.
- a desired pattern can be formed by alkaline development.
- the acid value of the resin having an acid group is preferably 30 to 500 mgKOH / g.
- the lower limit is preferably 50 mgKOH / g or more, and more preferably 70 mgKOH / g or more.
- the upper limit is preferably 400 mgKOH / g or less, more preferably 200 mgKOH / g or less, further preferably 150 mgKOH / g or less, and most preferably 120 mgKOH / g or less.
- the coloring composition of the present invention preferably contains a resin having a basic group.
- the resin having a basic group is preferably a resin containing a repeating unit having a basic group in the side chain, and a copolymer having a repeating unit having a basic group in the side chain and a repeating unit not containing a basic group.
- a polymer is more preferable, and a block copolymer having a repeating unit having a basic group in the side chain and a repeating unit not containing a basic group is further preferable.
- a resin having a basic group can also be used as a dispersant.
- the amine value of the resin having a basic group is preferably 5 to 300 mgKOH / g.
- the lower limit is preferably 10 mgKOH / g or more, and more preferably 20 mgKOH / g or more.
- the upper limit is preferably 200 mgKOH / g or less, and more preferably 100 mgKOH / g or less.
- Examples of the basic group contained in the resin having a basic group include a group represented by the following formula (a-1) and a group represented by the following formula (a-2).
- Ra1 and Ra2 each independently represent a hydrogen atom, an alkyl group or an aryl group, and Ra1 and Ra2 may be bonded to each other to form a ring;
- R a11 represents a hydrogen atom, a hydroxy group, an alkyl group, an alkoxy group, an aryl group, an aryloxy group, an acyl group or an oxy radical
- R a12 ⁇ R a19 are each independently , Hydrogen atom, alkyl group or aryl group.
- R a1, R a2, R a11 number of carbon atoms of the alkyl group represented by ⁇ R a19 is 1-30, more preferably 1-15, more preferably 1-8, particularly preferably 1-5.
- the alkyl group may be linear, branched or cyclic, preferably linear or branched, more preferably linear.
- the alkyl group may have a substituent.
- R a1, R a2, R a11 ⁇ number of carbon atoms of the aryl group R a19 represents is preferably 6 to 30, more preferably 6 to 20, more preferably 6 to 12.
- the aryl group may have a substituent.
- the number of carbon atoms of the alkoxy group R a11 represents 1 to 30, more preferably 1 to 15, more preferably 1-8, particularly preferably 1-5.
- the alkoxy group may have a substituent.
- the aryloxy group represented by Ra11 preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 12 carbon atoms.
- the aryloxy group may have a substituent.
- the number of carbon atoms of the acyl group R a11 represents from 2 to 30, more preferably 2 to 20, 2 to 12 is more preferred.
- the acyl group may have a substituent.
- Block copolymer A1 which has been prepared can also be used, and these contents are incorporated in the present specification.
- the coloring composition of the present invention contains a resin having an acid group and a resin having a basic group, respectively. According to this aspect, the storage stability of the coloring composition can be further improved.
- the content of the resin having a basic group may be 20 to 500 parts by mass with respect to 100 parts by mass of the resin having an acid group. It is preferably 30 to 300 parts by mass, more preferably 50 to 200 parts by mass.
- the resin contains a repeating unit derived from a compound represented by the following formula (ED1) and / or a compound represented by the following formula (ED2) (hereinafter, these compounds may be referred to as “ether dimer”). It is also preferable to contain a resin.
- R 1 and R 2 each independently represent a hydrocarbon group having 1 to 25 carbon atoms which may have a hydrogen atom or a substituent.
- R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms.
- the description in JP-A-2010-168539 can be referred to.
- paragraph number 0317 of JP2013-209760A can be referred to, and the content thereof is incorporated in the present specification.
- the resin contains a resin containing a repeating unit having a polymerizable group.
- the resin preferably contains a resin containing a repeating unit derived from the compound represented by the formula (X).
- R 1 represents a hydrogen atom or a methyl group
- R 21 and R 22 each independently represent an alkylene group
- n represents an integer of 0 to 15.
- the alkylene group represented by R 21 and R 22 preferably has 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms, further preferably 1 to 3 carbon atoms, and particularly preferably 2 or 3 carbon atoms.
- n represents an integer of 0 to 15, preferably an integer of 0 to 5, more preferably an integer of 0 to 4, and even more preferably an integer of 0 to 3.
- Examples of the compound represented by the formula (X) include ethylene oxide of paracumylphenol or propylene oxide-modified (meth) acrylate.
- Examples of commercially available products include Aronix M-110 (manufactured by Toagosei Co., Ltd.).
- the resin contains a resin having an aromatic carboxyl group (hereinafter, also referred to as resin Ac).
- the aromatic carboxyl group may be contained in the main chain of the repeating unit or may be contained in the side chain of the repeating unit.
- the aromatic carboxyl group is preferably contained in the main chain of the repeating unit.
- an aromatic carboxyl group is a group having a structure in which one or more carboxyl groups are bonded to an aromatic ring.
- the number of carboxyl groups bonded to the aromatic ring is preferably 1 to 4, and more preferably 1 to 2.
- the resin Ac is preferably a resin containing at least one repeating unit selected from the repeating unit represented by the formula (Ac-1) and the repeating unit represented by the formula (Ac-2).
- Ar 1 represents a group containing an aromatic carboxyl group
- L 1 represents -COO- or -CONH-
- L 2 represents a divalent linking group
- Ar 10 represents a group containing an aromatic carboxyl group
- L 11 represents -COO- or -CONH-
- L 12 represents a trivalent linking group
- P 10 is a polymer. Represents a chain.
- Examples of the group containing an aromatic carboxyl group represented by Ar 1 in the formula (Ac-1) include a structure derived from an aromatic tricarboxylic acid anhydride, a structure derived from an aromatic tetracarboxylic acid anhydride, and the like.
- Examples of the aromatic tricarboxylic acid anhydride and the aromatic tetracarboxylic acid anhydride include compounds having the following structures.
- Q 1 is represented by a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2- , -C (CF 3 ) 2- , and the following formula (Q-1). Represents a group to be used or a group represented by the following formula (Q-2).
- Specific examples of the group containing an aromatic carboxyl group represented by Ar 1 include a group represented by the formula (Ar-11), a group represented by the formula (Ar-12), and a group represented by the formula (Ar-13). Examples include the base.
- n1 represents an integer of 1 to 4, preferably 1 or 2, and more preferably 2.
- n2 represents an integer of 1 to 8, preferably an integer of 1 to 4, more preferably 1 or 2, and even more preferably 2.
- n3 and n4 each independently represent an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1 or 2, and preferably 1. More preferred. However, at least one of n3 and n4 is an integer of 1 or more.
- Q 1 is a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2- , -C (CF 3 ) 2- , and the above formula (Q-). It represents a group represented by 1) or a group represented by the above formula (Q-2).
- L 1 represents -COO- or -CONH-, and preferably -COO-.
- the divalent linking group represented by L 2 in the formula (Ac-1) includes an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S- and these.
- a group that combines two or more of the above can be mentioned.
- the alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 1 to 15 carbon atoms.
- the alkylene group may be linear, branched or cyclic.
- the arylene group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 10 carbon atoms.
- the alkylene group and the arylene group may have a substituent.
- the substituent include a hydroxy group and the like.
- the divalent linking group L 2 represents is preferably a group represented by -O-L 2a -O-.
- L 2a is an alkylene group; an arylene group; a group combining an alkylene group and an arylene group; at least one selected from an alkylene group and an arylene group, and —O—, ⁇ CO ⁇ , ⁇ COO ⁇ , —OCO ⁇ , Examples thereof include a group in which at least one selected from -NH- and -S- is combined.
- the alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 1 to 15 carbon atoms.
- the alkylene group may be linear, branched or cyclic.
- the alkylene group and the arylene group may have a substituent. Examples of the substituent include a hydroxy group and the like.
- the group containing the aromatic carboxyl group represented by Ar 10 in the formula (Ac-2) has the same meaning as Ar 1 in the formula (Ac-1), and the preferable range is also the same.
- L 11 represents -COO- or -CONH-, and preferably -COO-.
- Hydrocarbon groups, -O-, -CO-, -COO-, -OCO-, -NH-, -S- and two of these are the trivalent linking groups represented by L 12 in the formula (Ac-2).
- the hydrocarbon group include an aliphatic hydrocarbon group and an aromatic hydrocarbon group.
- the number of carbon atoms of the aliphatic hydrocarbon group is preferably 1 to 30, more preferably 1 to 20, and even more preferably 1 to 15.
- the aliphatic hydrocarbon group may be linear, branched or cyclic.
- the number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 10.
- the hydrocarbon group may have a substituent. Examples of the substituent include a hydroxy group and the like.
- P 10 represents a polymer chain.
- the polymer chain represented by P 10 preferably has at least one repeating unit selected from poly (meth) acrylic repeating units, polyether repeating units, polyester repeating units and polyol repeating units.
- the weight average molecular weight of the polymer chain P 10 is preferably 500 to 20,000.
- the lower limit is preferably 1000 or more.
- the upper limit is preferably 10,000 or less, more preferably 5000 or less, and even more preferably 3000 or less.
- the weight average molecular weight of P 10 is in the above range, the dispersibility of the pigment in the composition is good.
- the resin having an aromatic carboxyl group is a resin having a repeating unit represented by the formula (Ac-2), this resin is preferably used as a dispersant.
- the resin preferably contains a resin as a dispersant.
- the dispersant include an acidic dispersant (acidic resin) and a basic dispersant (basic resin).
- the acidic dispersant (acidic resin) represents a resin in which the amount of acid groups is larger than the amount of basic groups.
- the acidic dispersant (acidic resin) a resin having an acid group amount of 70 mol% or more is preferable when the total amount of the acid group amount and the basic group amount is 100 mol%.
- the acid group of the acidic dispersant (acidic resin) is preferably a carboxyl group.
- the acid value of the acidic dispersant (acidic resin) is preferably 10 to 105 mgKOH / g.
- the basic dispersant represents a resin in which the amount of basic groups is larger than the amount of acid groups.
- a resin in which the amount of basic groups exceeds 50 mol% is preferable when the total amount of the amount of acid groups and the amount of basic groups is 100 mol%.
- the basic group contained in the basic dispersant is preferably an amino group.
- the resin used as the dispersant is also preferably a graft resin.
- graft resin the description in paragraphs 0025 to 0094 of JP2012-255128A can be referred to, and the content thereof is incorporated in the present specification.
- the resin used as the dispersant is also preferably a resin having an aromatic carboxyl group (resin Ac).
- resin Ac resin having an aromatic carboxyl group
- examples of the resin having an aromatic carboxyl group include those described above.
- the resin used as the dispersant is a polyimine-based dispersant containing a nitrogen atom in at least one of the main chain and the side chain.
- the polyimine-based dispersant has a main chain having a partial structure having a functional group of pKa14 or less, a side chain having 40 to 10,000 atoms, and a basic nitrogen atom in at least one of the main chain and the side chain.
- the resin to have is preferable.
- the basic nitrogen atom is not particularly limited as long as it is a nitrogen atom exhibiting basicity.
- the description in paragraphs 0102 to 0166 of JP2012-255128A can be referred to, and this content is incorporated in the present specification.
- the resin used as the dispersant is also preferably a resin having a structure in which a plurality of polymer chains are bonded to the core portion.
- resins include dendrimers (including star-shaped polymers).
- specific examples of the dendrimer include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP2013-043962.
- the resin used as the dispersant is also preferably a resin containing a repeating unit having an ethylenically unsaturated bond-containing group in the side chain.
- the content of the repeating unit having an ethylenically unsaturated bond-containing group in the side chain is preferably 10 mol% or more, more preferably 10 to 80 mol%, and 20 to 70 in all the repeating units of the resin. It is more preferably mol%.
- the resin described in JP-A-2018-087939 can also be used as the dispersant.
- Dispersants are also available as commercial products, and specific examples thereof include DISPERBYK series manufactured by Big Chemie Japan, SOLSPERSE series manufactured by Japan Lubrizol, Efka series manufactured by BASF, and Ajinomoto Fine-Techno (Ajinomoto Fine-Techno). Examples include the Ajispar series manufactured by Co., Ltd. Further, the product described in paragraph number 0129 of JP2012-137564A and the product described in paragraph number 0235 of JP2017-194662 can also be used as a dispersant.
- the block copolymers (EB-1) to (EB-9) described in paragraphs 0219 to 0221 of Japanese Patent No. 6432077 can also be used.
- the content of the resin in the total solid content of the coloring composition is preferably 1 to 60% by mass.
- the lower limit is preferably 5% by mass or more, more preferably 10% by mass or more, further preferably 15% by mass or more, and particularly preferably 20% by mass or more.
- the upper limit is preferably 50% by mass or less, more preferably 40% by mass or less.
- the coloring composition of the present invention may contain only one type of resin, or may contain two or more types of resin. When two or more kinds of resins are contained, it is preferable that the total amount thereof is within the above range.
- the coloring composition of the present invention contains a solvent.
- the solvent include organic solvents.
- the type of solvent is basically not particularly limited as long as it satisfies the solubility of each component and the coatability of the composition.
- the organic solvent include ester solvents, ketone solvents, alcohol solvents, amide solvents, ether solvents, hydrocarbon solvents and the like.
- paragraph No. 0223 of WO 2015/166779 can be referred to, the contents of which are incorporated herein by reference.
- an ester solvent substituted with a cyclic alkyl group and a ketone solvent substituted with a cyclic alkyl group can also be preferably used.
- organic solvent examples include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2 -Heptanone, cyclohexanone, cyclohexyl acetate, cyclopentanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N, N-dimethylpropanamide, 3-butoxy-N , N-Dimethylpropanamide and the like.
- aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may need to be reduced for environmental reasons (for example, 50 mass ppm (parts) with respect to the total amount of organic solvent. Per million) or less, 10 mass ppm or less, or 1 mass ppm or less).
- an organic solvent having a low metal content it is preferable to use an organic solvent having a low metal content, and the metal content of the organic solvent is preferably, for example, 10 mass ppb (parts per parts) or less. If necessary, an organic solvent at the mass ppt (parts per parts) level may be used, and such an organic solvent is provided by, for example, Toyo Synthetic Co., Ltd. (The Chemical Daily, November 13, 2015). ..
- Examples of the method for removing impurities such as metals from the organic solvent include distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter.
- the filter pore diameter of the filter used for filtration is preferably 10 ⁇ m or less, more preferably 5 ⁇ m or less, and even more preferably 3 ⁇ m or less.
- the filter material is preferably polytetrafluoroethylene, polyethylene or nylon.
- the organic solvent may contain isomers (compounds having the same number of atoms but different structures). Further, only one kind of isomer may be contained, or a plurality of kinds may be contained.
- the content of peroxide in the organic solvent is preferably 0.8 mmol / L or less, and more preferably substantially free of peroxide.
- the content of the solvent in the coloring composition is preferably 10 to 95% by mass, more preferably 20 to 90% by mass, and even more preferably 30 to 90% by mass.
- the coloring composition of the present invention does not substantially contain an environmentally regulated substance from the viewpoint of environmental regulation.
- substantially free of the environmentally regulated substance means that the content of the environmentally regulated substance in the coloring composition is 50 mass ppm or less, and preferably 30 mass ppm or less. It is more preferably 10 mass ppm or less, and particularly preferably 1 mass ppm or less.
- the environmentally regulated substance include benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene.
- Examples of the method for reducing the environmentally regulated substance include a method of heating or depressurizing the inside of the system to raise the boiling point of the environmentally regulated substance to the boiling point or higher, and distilling off the environmentally regulated substance from the system to reduce the amount of the environmentally regulated substance. Further, when distilling off a small amount of an environmentally regulated substance, it is also useful to azeotrope with a solvent having a boiling point equivalent to that of the solvent in order to improve efficiency.
- a polymerization inhibitor or the like is added and distilled under reduced pressure in order to prevent the radical polymerization reaction from proceeding and cross-linking between molecules during distillation under reduced pressure. You may.
- distillation methods are the stage of the raw material, the stage of the product obtained by reacting the raw material (for example, the resin solution after polymerization or the polyfunctional monomer solution), or the stage of the coloring composition prepared by mixing these compounds. It is possible at any stage such as.
- the coloring composition of the present invention can contain a pigment derivative.
- the pigment derivative include compounds having a structure in which an acid group or a basic group is bonded to the pigment skeleton.
- the pigment skeletons constituting the pigment derivatives include quinoline pigment skeleton, benzoimidazolone pigment skeleton, benzoisoindole pigment skeleton, benzothiazole pigment skeleton, inimium pigment skeleton, squarylium pigment skeleton, croconium pigment skeleton, oxonor pigment skeleton, and pyrolopyrrolop pigment.
- Examples of the acid group include a sulfo group, a carboxyl group, a phosphoric acid group and salts thereof.
- the atoms or groups that make up the salt include alkali metal ions (Li + , Na + , K +, etc.), alkaline earth metal ions (Ca 2+ , Mg 2+, etc.), ammonium ions, imidazolium ions, pyridinium ions, etc.
- Examples include phosphonium ions.
- Examples of the basic group include an amino group, a pyridinyl group and a salt thereof, a salt of an ammonium group, and a phthalimide methyl group.
- Examples of the atom or atomic group constituting the salt include hydroxide ion, halogen ion, carboxylic acid ion, sulfonic acid ion, and phenoxide ion.
- the pigment derivative it is also preferable to use a compound having a triazine skeleton and a structure having an acid group or a basic group. Since the structure of the triazine skeleton of the pigment derivative and the pteridine skeleton of the pteridine pigment are similar, the pigment derivative is easily adsorbed on the surface of the pteridine pigment, and as a result, the pteridine pigment, the pigment derivative and the resin are strong. It is presumed that a network will be formed. By forming such a network, the dispersibility of the pteridine pigment in the coloring composition can be further improved, and the stability of the coloring composition with time can be further improved. Furthermore, it is easy to form a film in which the occurrence of defects is suppressed. Further, by strengthening the network of the pigment and the resin, the pigment can be easily developed together with the resin, and the developability can be further improved.
- a pigment derivative having excellent visible transparency (hereinafter, also referred to as a transparent pigment derivative) can be contained.
- the maximum value of the molar extinction coefficient in the wavelength region of 400 ⁇ 700 nm of the transparent pigment derivative (.epsilon.max) is that it is preferable, 1000L ⁇ mol -1 ⁇ cm -1 or less is not more than 3000L ⁇ mol -1 ⁇ cm -1 Is more preferable, and 100 L ⁇ mol -1 ⁇ cm -1 or less is further preferable.
- the lower limit of ⁇ max is, for example, 1 L ⁇ mol -1 ⁇ cm -1 or more, and may be 10 L ⁇ mol -1 ⁇ cm -1 or more.
- pigment derivative examples include the compounds described in Examples described later, Japanese Patent Application Laid-Open No. 56-118462, Japanese Patent Application Laid-Open No. 63-246674, Japanese Patent Application Laid-Open No. 01-2170777, and Japanese Patent Application Laid-Open No. 03-009961. , Japanese Patent Application Laid-Open No. 03-026767, Japanese Patent Application Laid-Open No. 03-153780, Japanese Patent Application Laid-Open No. 03-045662, Japanese Patent Application Laid-Open No. 04-285669, Japanese Patent Application Laid-Open No. 06-145546, Japanese Patent Application Laid-Open No. 06-212088, Kaihei 06-240158, Japanese Patent Application Laid-Open No.
- the content of the pigment derivative is preferably 1 to 30 parts by mass, more preferably 2 to 15 parts by mass, still more preferably 4 to 10 parts by mass with respect to 100 parts by mass of the pigment. Only one type of pigment derivative may be used, or two or more types may be used in combination. When two or more kinds are used in combination, the total amount thereof is preferably in the above range.
- the coloring composition of the present invention can further contain an infrared absorber.
- an infrared transmission filter is formed using the coloring composition of the present invention, the wavelength of light transmitted through the film obtained by containing an infrared absorber in the coloring composition is shifted to a longer wavelength side.
- the infrared absorber is preferably a compound having a maximum absorption wavelength on the longer wavelength side than the wavelength of 700 nm.
- the infrared absorber is preferably a compound having a maximum absorption wavelength in the range of more than 700 nm and 1800 nm or less.
- the ratio A 1 / A 2 between the absorbance A 2 in the absorbance A 1 and the maximum absorption wavelength in the wavelength 500nm of the infrared absorbing agent is preferably 0.08 or less, and more preferably 0.04 or less ..
- infrared absorbers examples include pyrolopyrrole compounds, cyanine compounds, squarylium compounds, phthalocyanine compounds, naphthalocyanine compounds, quaterylene compounds, merocyanine compounds, croconium compounds, oxonor compounds, iminium compounds, dithiol compounds, triarylmethane compounds, pyromethene compounds, and azomethine compounds.
- examples thereof include compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, and metal boroides.
- Examples of the pyrolopyrrole compound include the compounds described in paragraphs 0016 to 0058 of JP2009-263614, the compounds described in paragraphs 0037 to 0052 of JP2011-066731, and International Publication No. 2015/166783. Examples thereof include the compounds described in paragraphs 0010 to 0033.
- Examples of the squarylium compound include the compounds described in paragraphs 0044 to 0049 of JP2011-208101A, the compounds described in paragraphs 0060 to 0061 of Patent No. 6065169, and paragraph numbers 0040 of International Publication No. 2016/181987. , The compound described in JP-A-2015-176046, the compound described in paragraph number 0072 of International Publication No.
- JP2012-077153 the oxytitanium phthalocyanine described in JP2006-343631, and paragraphs 0013 to 0029 of JP2013-195480.
- vanadium phthalocyanine compound described in Japanese Patent No. 6081771.
- examples of the naphthalocyanine compound include the compounds described in paragraph No. 0093 of JP2012-077153.
- Examples of the dithiolene metal complex include the compounds described in Japanese Patent No. 5733804.
- the metal oxide include indium tin oxide, antimonthine oxide, zinc oxide, Al-doped zinc oxide, fluorine-doped tin dioxide, niobium-doped titanium dioxide, and tungsten oxide.
- tungsten oxide paragraph number 0080 of JP-A-2016-006476 can be referred to, and the contents thereof are incorporated in the present specification.
- the metal boride include lanthanum hexaboride. Examples of commercially available lanthanum boride, LaB 6 -F (manufactured by Japan New Metals Co., Ltd.), and the like. Further, as the metal boride, the compound described in International Publication No. 2017/119394 can also be used. Examples of commercially available indium tin oxide products include F-ITO (manufactured by DOWA Hi-Tech Co., Ltd.).
- Examples of the infrared absorber include a squarylium compound described in JP-A-2017-197437, a squarylium compound described in JP-A-2017-025311, a squarylium compound described in International Publication No. 2016/154782, and Patent No. 5884953.
- Squalylium compounds described in Japanese Patent Publication No. 6036689 Squalylium compounds described in Japanese Patent No. 581604, Squalylium compounds described in International Publication No. 2017/213047, paragraph numbers 0090 to 0107, specially mentioned.
- Linked squalylium compound compound having a pyrrolbis-type squalylium skeleton or croconium skeleton described in JP-A-2017-141215, dihydrocarbazolebis-type squalylium compound described in JP-A-2017-082029, JP-A-2017-068120
- the asymmetric compound described in paragraphs 0027 to 0114 of Japanese Patent Application Laid-Open No. 2017, the pyrrole ring-containing compound (carbazole type) described in JP-A-2017-067963, the phthalocyanine compound described in Japanese Patent No. 6251530, and the like are used. You can also do it.
- the content of the infrared absorber in the total solid content of the coloring composition is preferably 1 to 40% by mass.
- the lower limit is preferably 2% by mass or more, more preferably 5% by mass or more, and further preferably 10% by mass or more.
- the upper limit is preferably 30% by mass or less, more preferably 25% by mass or less.
- the coloring composition of the present invention may contain only one type of infrared absorber, or may contain two or more types of infrared absorbers. When two or more kinds of infrared absorbers are contained, the total amount thereof is preferably in the above range.
- the coloring composition of the present invention can contain a polymerizable compound.
- a polymerizable compound a known compound that can be crosslinked by radicals, acids or heat can be used.
- the polymerizable compound is preferably, for example, a compound having an ethylenically unsaturated bond-containing group.
- the ethylenically unsaturated bond-containing group include a vinyl group, a (meth) allyl group, and a (meth) acryloyl group.
- the polymerizable compound used in the present invention is preferably a radically polymerizable compound.
- the polymerizable compound may be in any chemical form such as a monomer, a prepolymer, or an oligomer, but a monomer is preferable.
- the molecular weight of the polymerizable compound is preferably 100 to 3000.
- the upper limit is more preferably 2000 or less, and even more preferably 1500 or less.
- the lower limit is more preferably 150 or more, and even more preferably 250 or more.
- the polymerizable compound is preferably a compound containing 3 or more ethylenically unsaturated bond-containing groups, more preferably a compound containing 3 to 15 ethylenically unsaturated bond-containing groups, and an ethylenically unsaturated bond. It is more preferable that the compound contains 3 to 6 containing groups.
- the polymerizable compound is preferably a (meth) acrylate compound having 3 to 15 functionalities, and more preferably a (meth) acrylate compound having 3 to 6 functionalities.
- polymerizable compound examples include paragraph numbers 0905 to 0108 of JP2009-288705A, paragraphs 0227 of JP2013-209760A, paragraphs 0254 to 0257 of JP2008-292970, and JP-A.
- the compounds described in paragraphs 0034 to 0038 of Japanese Patent Application Laid-Open No. 2013-253224, paragraph numbers 0477 of Japanese Patent Application Laid-Open No. 2012-208494, Japanese Patent Application Laid-Open No. 2017-048367, Japanese Patent No. 6057891 and Japanese Patent No. 6031807 are These contents are incorporated herein by reference.
- dipentaerythritol tri (meth) acrylate commercially available KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.
- dipentaerythritol tetra (meth) acrylate commercially available KAYARAD D-320) ; Nippon Kayaku Co., Ltd.
- Dipentaerythritol penta (meth) acrylate commercially available KAYARAD D-310; Nihon Kayaku Co., Ltd.
- dipentaerythritol hexa (meth) acrylate commercially available
- KAYARAD DPHA manufactured by Nippon Kayaku Co., Ltd.
- NK ester A-DPH-12E manufactured by Shin-Nakamura Chemical Industry Co., Ltd.
- these (meth) acryloyl groups via ethylene glycol and / or propylene glycol residues.
- SR454, SR499 commercially available from Sartmer
- polymerizable compounds diglycerin EO (ethylene oxide) modified (meth) acrylate (commercially available M-460; manufactured by Toa Synthetic), pentaerythritol tetraacrylate (manufactured by Shin-Nakamura Chemical Co., Ltd., NK ester A) -TMMT), 1,6-hexanediol diacrylate (manufactured by Nippon Kayaku Co., Ltd., KAYARAD HDDA), RP-1040 (manufactured by Nippon Kayaku Co., Ltd.), Aronix TO-2349 (manufactured by Toa Synthetic Co., Ltd.) , NK Oligo UA-7200 (manufactured by Shin-Nakamura Chemical Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.),
- Examples of the polymerizable compound include trimethylolpropane tri (meth) acrylate, trimethylolpropane propylene oxide-modified tri (meth) acrylate, trimethylolpropane ethylene oxide-modified tri (meth) acrylate, and isocyanurate ethylene oxide-modified tri (meth) acrylate.
- Trifunctional (meth) acrylate compounds such as pentaerythritol trimethylolpropane (meth) acrylate can also be used.
- Commercially available trifunctional (meth) acrylate compounds include Aronix M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306, and M-305.
- M-303, M-452, M-450 manufactured by Toa Synthetic Co., Ltd.
- NK ester A9300, A-GLY-9E, A-GLY-20E, A-TMM-3, A-TMM-3L, A -TMM-3LM-N, A-TMPT, TMPT manufactured by Shin Nakamura Chemical Industry Co., Ltd.
- KAYARAD GPO-303, TMPTA, THE-330, TPA-330, PET-30 (manufactured by Nippon Kayaku Co., Ltd.) And so on.
- a compound having an acid group can also be used as the polymerizable compound.
- the polymerizable compound having an acid group By using a polymerizable compound having an acid group, the polymerizable compound in the unexposed portion can be easily removed during development, and the generation of development residue can be suppressed.
- the acid group include a carboxyl group, a sulfo group, a phosphoric acid group and the like, and a carboxyl group is preferable.
- Examples of commercially available products of the polymerizable compound having an acid group include Aronix M-510, M-520, and Aronix TO-2349 (manufactured by Toagosei Co., Ltd.).
- the preferable acid value of the polymerizable compound having an acid group is 0.1 to 40 mgKOH / g, and more preferably 5 to 30 mgKOH / g.
- the acid value of the polymerizable compound is 0.1 mgKOH / g or more, the solubility in a developing solution is good, and when it is 40 mgKOH / g or less, it is advantageous in production and handling.
- a compound having a caprolactone structure can also be used.
- examples of commercially available products of the polymerizable compound having a caprolactone structure include KAYARAD DPCA-20, DPCA-30, DPCA-60, DPCA-120 (all manufactured by Nippon Kayaku Co., Ltd.) and the like.
- a polymerizable compound having an alkyleneoxy group can also be used.
- a polymerizable compound having an ethyleneoxy group and / or a propyleneoxy group is preferable, a polymerizable compound having an ethyleneoxy group is more preferable, and 3 to 3 having 4 to 20 ethyleneoxy groups.
- a hexafunctional (meth) acrylate compound is more preferred.
- Examples of the polymerizable compound having an alkyleneoxy group include compounds having the following structures.
- SR-494 which is a tetrafunctional (meth) acrylate having four ethyleneoxy groups manufactured by Sartmer, and a trifunctional (meth) having three isobutyleneoxy groups.
- KAYARAD TPA-330 manufactured by Nippon Kayaku Co., Ltd., which is an acrylate, and the like can be mentioned.
- a polymerizable compound having a fluorene skeleton can also be used.
- examples of commercially available products of the polymerizable compound having a fluorene skeleton include Ogsol EA-0200 and EA-0300 (manufactured by Osaka Gas Chemical Co., Ltd., a (meth) acrylate monomer having a fluorene skeleton).
- the polymerizable compound it is also preferable to use a compound that does not substantially contain an environmentally regulated substance such as toluene.
- an environmentally regulated substance such as toluene.
- commercially available products of such compounds include KAYARAD DPHA LT and KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.).
- the content of the polymerizable compound in the total solid content of the coloring composition is preferably 0.1 to 50% by mass.
- the lower limit is more preferably 0.5% by mass or more, and further preferably 1% by mass or more.
- the upper limit is more preferably 45% by mass or less, further preferably 40% by mass or less.
- the polymerizable compound may be used alone or in combination of two or more. When two or more kinds are used in combination, it is preferable that the total of them is in the above range.
- the coloring composition of the present invention can contain a photopolymerization initiator.
- the photopolymerization initiator is not particularly limited and may be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light rays in the ultraviolet region to the visible region is preferable.
- the photopolymerization initiator is preferably a photoradical polymerization initiator.
- photopolymerization initiator examples include halogenated hydrocarbon derivatives (for example, compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazoles, oxime compounds, organic peroxides, and thio compounds. , Ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds and the like.
- the photopolymerization initiator is a trihalomethyltriazine compound, a benzyl dimethyl ketal compound, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, an acylphosphine compound, a phosphine oxide compound, a metallocene compound, an oxime compound, or a triarylimidazole.
- It is preferably a dimer, an onium compound, a benzothiazole compound, a benzophenone compound, an acetophenone compound, a cyclopentadiene-benzene-iron complex, a halomethyloxaziazole compound and a 3-aryl substituted coumarin compound, and an oxime compound and an ⁇ -hydroxyketone compound.
- ⁇ -Aminoketone compound, and an acylphosphine compound are more preferable, and an oxime compound is further preferable.
- the photopolymerization initiator the compounds described in paragraphs 0065 to 0111 of JP-A-2014-130173 and JP-A-6301489, MATERIAL STAGE 37-60p, vol.
- ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (all manufactured by IGM Resins BV), Irgacure 184, Irgacure 1173, Irgacare 1173, Irgacure29. (Manufactured by the company) and the like.
- Commercially available ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (above, IGM Resins BV), Irgacare 907, Irgacare 369, Irgacure 369, Irgacure 369, Irgar (Made) and so on.
- acylphosphine compounds examples include Omnirad 819, Omnirad TPO (above, manufactured by IGM Resins BV), Irgacure 819, and Irgacure TPO (above, manufactured by BASF).
- Examples of the oxime compound include the compounds described in JP-A-2001-233842, the compounds described in JP-A-2000-080068, and the compounds described in JP-A-2006-342166.
- oxime compound examples include 3-benzoyloxyiminobutane-2-one, 3-acetoxyiminobutane-2-one, 3-propionyloxyiminovtan-2-one, 2-acetoxyimiminopentane-3-one, 2-acetoxyimino-1-phenylpropane-1-one, 2-benzoyloxyimino-1-phenylpropane-1-one, 3- (4-toluenesulfonyloxy) iminobutane-2-one, and 2-ethoxycarbonyloxy Examples thereof include imino-1-phenylpropane-1-one.
- an oxime compound having a fluorene ring can also be used.
- Specific examples of the oxime compound having a fluorene ring include the compounds described in JP-A-2014-137466.
- an oxime compound having a skeleton in which at least one benzene ring of the carbazole ring is a naphthalene ring can also be used.
- Specific examples of such an oxime compound include the compounds described in International Publication No. 2013/083505.
- an oxime compound having a fluorine atom can also be used as the photopolymerization initiator.
- Specific examples of the oxime compound having a fluorine atom are described in the compounds described in JP-A-2010-262028, compounds 24, 36-40 described in JP-A-2014-500852, and JP-A-2013-164471. Compound (C-3) and the like.
- an oxime compound having a nitro group can be used as the photopolymerization initiator.
- the oxime compound having a nitro group is also preferably a dimer.
- Specific examples of the oxime compound having a nitro group include the compounds described in paragraphs 0031 to 0047 of JP2013-114249A and paragraphs 0008-0012 and 0070-0079 of JP2014-137466. Examples thereof include the compound described in paragraphs 0007 to 0025 of Japanese Patent No. 4223071, ADEKA ARKULS NCI-831 (manufactured by ADEKA Corporation).
- an oxime compound having a benzofuran skeleton can also be used.
- Specific examples include OE-01 to OE-75 described in International Publication No. 2015/036910.
- an oxime compound in which a substituent having a hydroxy group is bonded to the carbazole skeleton can also be used.
- Examples of such a photopolymerization initiator include the compounds described in International Publication No. 2019/088055.
- the oxime compound is preferably a compound having a maximum absorption wavelength in the wavelength range of 350 to 500 nm, and more preferably a compound having a maximum absorption wavelength in the wavelength range of 360 to 480 nm.
- the molar extinction coefficient of the oxime compound at a wavelength of 365 nm or a wavelength of 405 nm is preferably high, more preferably 1000 to 300,000, further preferably 2000 to 300,000, and more preferably 5000 to 200,000. It is particularly preferable to have.
- the molar extinction coefficient of a compound can be measured using a known method. For example, it is preferable to measure at a concentration of 0.01 g / L using an ethyl acetate solvent with a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian).
- Irgacure OXE01 manufactured by BASF
- Irgacure OXE02 manufactured by BASF
- Omnirad 2959 manufactured by IGM Resins BV
- a bifunctional or trifunctional or higher functional photoradical polymerization initiator may be used as the photopolymerization initiator.
- a photoradical polymerization initiator two or more radicals are generated from one molecule of the photoradical polymerization initiator, so that good sensitivity can be obtained.
- the crystallinity is lowered, the solubility in a solvent or the like is improved, the precipitation is less likely to occur with time, and the stability of the coloring composition with time can be improved.
- Specific examples of the bifunctional or trifunctional or higher functional photo-radical polymerization initiators include JP-A-2010-527339, JP-A-2011-524436, International Publication No.
- the content of the photopolymerization initiator in the total solid content of the coloring composition is preferably 0.1 to 30% by mass.
- the lower limit is preferably 0.5% by mass or more, and more preferably 1% by mass or more.
- the upper limit is preferably 20% by mass or less, more preferably 15% by mass or less.
- only one type of photopolymerization initiator may be used, or two or more types may be used. When two or more kinds are used, it is preferable that the total amount thereof is within the above range.
- the coloring composition of the present invention can contain a compound having a cyclic ether group.
- the cyclic ether group include an epoxy group and an oxetanyl group.
- the compound having a cyclic ether group is preferably a compound having an epoxy group (hereinafter, also referred to as an epoxy compound). Examples of the epoxy compound are described in paragraphs 0034 to 0036 of JP2013-011869A, paragraph numbers 0147 to 0156 of JP2014-043556, and paragraph numbers 0085 to 0092 of JP2014-089408. Compounds, compounds described in JP-A-2017-179172 can also be used. These contents are incorporated herein by reference.
- the epoxy compound may be a small molecule compound (for example, a molecular weight of less than 2000, further, a molecular weight of less than 1000) or a polymer compound (for example, a molecular weight of 1000 or more, and in the case of a polymer, a weight average molecular weight of 1000 or more). But it may be.
- the weight average molecular weight of the epoxy compound is preferably 200 to 100,000, more preferably 500 to 50,000.
- the upper limit of the weight average molecular weight is preferably 10,000 or less, more preferably 5000 or less, and even more preferably 3000 or less.
- an epoxy resin can be preferably used as the epoxy compound.
- the epoxy resin include an epoxy resin which is a glycidyl etherified product of a phenol compound, an epoxy resin which is a glycidyl etherified product of various novolak resins, an alicyclic epoxy resin, an aliphatic epoxy resin, a heterocyclic epoxy resin, and a glycidyl ester.
- Examples thereof include a copolymer with another polymerizable unsaturated compound.
- the epoxy equivalent of the epoxy resin is preferably 310 to 3300 g / eq, more preferably 310 to 1700 g / eq, and even more preferably 310 to 1000 g / eq.
- EHPE3150 manufactured by Daicel Corporation
- EPICLON N-695 manufactured by DIC Corporation
- Marproof G-0150M G-0105SA, G-0130SP, G. -0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, G-01758 (all manufactured by Nichiyu Co., Ltd., epoxy group-containing polymer) and the like can be mentioned.
- the content of the compound having a cyclic ether group in the total solid content of the coloring composition is preferably 0.1 to 20% by mass.
- the lower limit is, for example, preferably 0.5% by mass or more, and more preferably 1% by mass or more.
- the upper limit is, for example, preferably 15% by mass or less, and more preferably 10% by mass or less.
- the compound having a cyclic ether group may be only one kind or two or more kinds. In the case of two or more types, it is preferable that the total amount thereof is within the above range.
- the coloring composition of the present invention may contain a curing accelerator.
- the curing accelerator include thiol compounds, methylol compounds, amine compounds, phosphonium salt compounds, amidin salt compounds, amide compounds, base generators, isocyanate compounds, alkoxysilane compounds, and onium salt compounds.
- Specific examples of the curing accelerator include the compounds described in paragraphs 0094 to 0097 of WO2018 / 056189, the compounds described in paragraphs 0246 to 0253 of JP2015-034963, and JP2013-041165. Compounds described in paragraphs 0186 to 0251 of Japanese Patent Application Laid-Open No. 0186 to 0251, ionic compounds described in Japanese Patent Application Laid-Open No.
- the coloring composition of the present invention can contain an ultraviolet absorber.
- an ultraviolet absorber a conjugated diene compound, an aminodiene compound, a salicylate compound, a benzophenone compound, a benzotriazole compound, an acrylonitrile compound, a hydroxyphenyltriazine compound, an indole compound, a triazine compound and the like can be used. Examples of such compounds include paragraph numbers 0038 to 0052 of JP2009-217221A, paragraph numbers 0052 to 0072 of JP2012-208374A, and paragraph numbers 0317 to 0334 of JP2013-068814.
- Examples include the compounds described in paragraphs 0061 to 0080 of JP 2016-162946, the contents of which are incorporated herein.
- Specific examples of the ultraviolet absorber include compounds having the following structures. Examples of commercially available ultraviolet absorbers include UV-503 (manufactured by Daito Kagaku Co., Ltd.). Examples of the benzotriazole compound include the MYUA series made by Miyoshi Oil & Fat Co., Ltd. (The Chemical Daily, February 1, 2016). Further, as the ultraviolet absorber, the compounds described in paragraphs 0049 to 0059 of Japanese Patent No. 6268967 can also be used.
- the content of the ultraviolet absorber in the total solid content of the coloring composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass.
- the content of the ultraviolet absorber in the total solid content of the coloring composition is preferably 0.01 to 10% by mass, more preferably 0.01 to 5% by mass.
- only one type of ultraviolet absorber may be used, or two or more types may be used.
- the total amount is preferably in the above range.
- the coloring composition of the present invention can contain a polymerization inhibitor.
- the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis (3-methyl-6-tert-butylphenol), and the like.
- examples thereof include 2,2'-methylenebis (4-methyl-6-t-butylphenol) and N-nitrosophenylhydroxyamine salts (ammonium salt, first cerium salt, etc.). Of these, p-methoxyphenol is preferable.
- the content of the polymerization inhibitor in the total solid content of the coloring composition is preferably 0.0001 to 5% by mass.
- the polymerization inhibitor may be only one type or two or more types. In the case of two or more types, the total amount is preferably in the above range.
- the coloring composition of the present invention can contain a silane coupling agent.
- the silane coupling agent means a silane compound having a hydrolyzable group and other functional groups.
- the hydrolyzable group refers to a substituent that is directly linked to a silicon atom and can form a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction.
- Examples of the hydrolyzable group include a halogen atom, an alkoxy group, an acyloxy group and the like, and an alkoxy group is preferable. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group.
- Examples of the functional group other than the hydrolyzable group include a vinyl group, a (meth) allyl group, a (meth) acryloyl group, a mercapto group, an epoxy group, an oxetanyl group, an amino group, a ureido group, a sulfide group and an isocyanate group.
- a phenyl group and the like preferably an amino group, a (meth) acryloyl group and an epoxy group.
- silane coupling agent examples include N- ⁇ -aminoethyl- ⁇ -aminopropylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Industry Co., Ltd., trade name KBM-602), N- ⁇ -aminoethyl- ⁇ -amino.
- Propyltrimethoxysilane (manufactured by Shinetsu Chemical Industry Co., Ltd., trade name KBM-603), N- ⁇ -aminoethyl- ⁇ -aminopropyltriethoxysilane (manufactured by Shinetsu Chemical Industry Co., Ltd., trade name KBE-602), ⁇ -Aminopropyltrimethoxysilane (manufactured by Shinetsu Chemical Industry Co., Ltd., trade name KBM-903), ⁇ -aminopropyltriethoxysilane (manufactured by Shinetsu Chemical Industry Co., Ltd., trade name KBE-903), 3-methacryloxy Propylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Industry Co., Ltd., trade name KBM-502), 3-methacryloxypropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Industry Co., Ltd.
- the silane coupling agent include the compounds described in paragraphs 0018 to 0036 of JP2009-288703 and the compounds described in paragraphs 0056 to 0066 of JP2009-242604A. , These contents are incorporated herein by reference.
- the content of the silane coupling agent in the total solid content of the coloring composition is preferably 0.01 to 15.0% by mass, more preferably 0.05 to 10.0% by mass. preferable.
- the silane coupling agent may be only one type or two or more types. In the case of two or more types, the total amount is preferably in the above range.
- the coloring composition of the present invention can contain a surfactant.
- a surfactant various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone-based surfactant can be used.
- the surfactant described in paragraph Nos. 0238 to 0245 of International Publication No. 2015/166779 is mentioned, and the content thereof is incorporated in the present specification.
- the surfactant is preferably a fluorine-based surfactant.
- a fluorine-based surfactant in the coloring composition, the liquid characteristics (particularly, fluidity) can be further improved, and the liquid saving property can be further improved. It is also possible to form a film having a small thickness unevenness.
- the fluorine content in the fluorine-based surfactant is preferably 3 to 40% by mass, more preferably 5 to 30% by mass, and particularly preferably 7 to 25% by mass.
- a fluorine-based surfactant having a fluorine content within this range is effective in terms of uniformity of coating film thickness and liquid saving property, and has good solubility in a coloring composition.
- fluorine-based surfactant examples include the surfactants described in paragraphs 0060 to 0064 of Japanese Patent Application Laid-Open No. 2014-041318 (paragraphs 0060 to 0064 of the corresponding International Publication No. 2014/017669) and the like, Japanese Patent Application Laid-Open No. 2011-.
- the surfactants described in paragraphs 0117 to 0132 of JP 132503 are mentioned and their contents are incorporated herein by reference.
- fluorine-based surfactants include, for example, Megafuck F171, F172, F173, F176, F177, F141, F142, F143, F144, R30, F437, F475, F479, F482, F554, F780, EXP, MFS.
- the fluorine-based surfactant has a molecular structure having a functional group containing a fluorine atom, and an acrylic compound in which a portion of the functional group containing a fluorine atom is cut off and the fluorine atom volatilizes when heat is applied.
- fluorine-based surfactants include Megafuck DS series manufactured by DIC Corporation (The Chemical Daily (February 22, 2016), Nikkei Sangyo Shimbun (February 23, 2016)), for example, Mega. Fuck DS-21 can be mentioned.
- fluorine-based surfactant it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound.
- a fluorine-based surfactant include the fluorine-based surfactants described in JP-A-2016-216602, the contents of which are incorporated in the present specification.
- the fluorine-based surfactant a block polymer can also be used.
- the fluorine-based surfactant has a repeating unit derived from a (meth) acrylate compound having a fluorine atom and 2 or more (preferably 5 or more) alkyleneoxy groups (preferably ethyleneoxy groups and propyleneoxy groups) (meth).
- a fluorine-containing polymer compound containing a repeating unit derived from an acrylate compound can also be preferably used.
- the fluorine-containing surfactants described in paragraphs 0016 to 0037 of JP-A-2010-032698 and the following compounds are also exemplified as the fluorine-based surfactants used in the present invention.
- the weight average molecular weight of the above compounds is preferably 3000 to 50000, for example 14000.
- % indicating the ratio of the repeating unit is mol%.
- a fluorine-based surfactant a fluorine-containing polymer having an ethylenically unsaturated bond-containing group in the side chain can also be used.
- the compounds described in paragraphs 0050 to 0090 and paragraph numbers 0289 to 0295 of JP2010-164965, Megafuck RS-101, RS-102, RS-718K manufactured by DIC Corporation, RS-72-K and the like can be mentioned.
- the fluorine-based surfactant the compounds described in paragraphs 0015 to 0158 of JP2015-117327A can also be used.
- Nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane and their ethoxylates and propoxylates (eg, glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, etc.
- silicone-based surfactant examples include Torre Silicone DC3PA, Torre Silicone SH7PA, Torre Silicone DC11PA, Torre Silicone SH21PA, Torre Silicone SH28PA, Torre Silicone SH29PA, Torre Silicone SH30PA, Torre Silicone SH8400 (all, Toray Dow Corning Co., Ltd.). ), TSF-4440, TSF-4300, TSF-4445, TSF-4460, TSF-4452 (above, manufactured by Momentive Performance Materials), KP-341, KF-6001, KF-6002 (above, (Shinetsu Silicone Co., Ltd.), BYK307, BYK323, BYK330 (all manufactured by Big Chemie) and the like.
- the content of the surfactant in the total solid content of the coloring composition is preferably 0.001% by mass to 5.0% by mass, more preferably 0.005 to 3.0% by mass. preferable.
- the surfactant may be only one kind or two or more kinds. In the case of two or more types, the total amount is preferably in the above range.
- the coloring composition of the present invention can contain an antioxidant.
- the antioxidant include phenol compounds, phosphite ester compounds, thioether compounds and the like.
- the phenol compound any phenol compound known as a phenolic antioxidant can be used.
- Preferred phenolic compounds include hindered phenolic compounds.
- a compound having a substituent at a site (ortho position) adjacent to the phenolic hydroxy group is preferable.
- a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferable.
- the antioxidant a compound having a phenol group and a phosphite ester group in the same molecule is also preferable.
- a phosphorus-based antioxidant can also be preferably used.
- the content of the antioxidant in the total solid content of the coloring composition is preferably 0.01 to 20% by mass, more preferably 0.3 to 15% by mass.
- containing an antioxidant only one type of antioxidant may be used, or two or more types may be used. When two or more types are used, the total amount is preferably in the above range.
- the coloring compositions of the present invention include sensitizers, curing accelerators, fillers, thermosetting accelerators, plasticizers and other auxiliaries (eg, conductive particles, fillers, defoamers, etc.). It may contain a flame retardant, a leveling agent, a peeling accelerator, a fragrance, a surface tension modifier, a chain transfer agent, etc.). By appropriately containing these components, properties such as film physical characteristics can be adjusted. These components are described in, for example, paragraph No. 0183 and subsequent paragraphs of JP2012-003225A (paragraph number 0237 of the corresponding US Patent Application Publication No. 2013/0034812), paragraphs of JP-A-2008-250074. The descriptions of Nos.
- the coloring composition of the present invention may contain a latent antioxidant, if necessary.
- the latent antioxidant is a compound in which the site that functions as an antioxidant is protected by a protecting group, and is heated at 100 to 250 ° C. or at 80 to 200 ° C. in the presence of an acid / base catalyst.
- a compound in which the protecting group is eliminated and functions as an antioxidant can be mentioned.
- Examples of the latent antioxidant include compounds described in International Publication No. 2014/021023, International Publication No. 2017/030005, and JP-A-2017-008219.
- Examples of commercially available products of latent antioxidants include ADEKA ARKULS GPA-5001 (manufactured by ADEKA Corporation) and the like. Further, as described in Japanese Patent Application Laid-Open No. 2018-155881, C.I. I. Pigment Yellow 129 may be added for the purpose of improving weather resistance.
- the coloring composition of the present invention may contain a metal oxide in order to adjust the refractive index of the obtained film.
- the metal oxide include TiO 2 , ZrO 2 , Al 2 O 3 , SiO 2 and the like.
- the primary particle size of the metal oxide is preferably 1 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. Further, in this case, the core portion may be hollow.
- the coloring composition of the present invention may contain a light resistance improving agent.
- the light resistance improving agent include the compounds described in paragraphs 0036 to 0037 of JP-A-2017-198787, the compounds described in paragraphs 0029 to 0034 of JP-A-2017-146350, and JP-A-2017-129774.
- the water content of the coloring composition of the present invention is usually 3% by mass or less, preferably 0.01 to 1.5% by mass, and more preferably 0.1 to 1.0% by mass.
- the water content can be measured by the Karl Fischer method.
- the coloring composition of the present invention can be used by adjusting the viscosity for the purpose of adjusting the film surface (flatness, etc.), adjusting the film thickness, and the like.
- the viscosity value can be appropriately selected as needed, but for example, at 25 ° C., 0.3 mPa ⁇ s to 50 mPa ⁇ s is preferable, and 0.5 mPa ⁇ s to 20 mPa ⁇ s is more preferable.
- a method for measuring the viscosity for example, a cone plate type viscometer can be used, and the viscosity can be measured in a state where the temperature is adjusted to 25 ° C.
- the container for the colored composition of the present invention is not particularly limited, and a known container can be used.
- a storage container for the purpose of suppressing impurities from being mixed into raw materials and compositions, a multi-layer bottle in which the inner wall of the container is composed of 6 types and 6 layers of resin and a bottle in which 6 types of resin are composed of 7 layers are used. It is also preferable to use it.
- Examples of such a container include the container described in Japanese Patent Application Laid-Open No. 2015-123351.
- the coloring composition of the present invention can be prepared by mixing the above-mentioned components. In preparing the coloring composition, all the components may be dissolved and / or dispersed in a solvent at the same time to prepare the coloring composition, or each component may be appropriately used as two or more solutions or dispersions, if necessary. Then, these may be mixed at the time of use (at the time of application) to prepare a coloring composition.
- the mechanical force used for dispersing the pigment includes compression, squeezing, impact, shearing, cavitation and the like.
- Specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high speed impellers, sand grinders, flow jet mixers, high pressure wet atomization, ultrasonic dispersion and the like.
- the process and disperser for dispersing pigments are "Dispersion Technology Complete Works, Published by Information Organization Co., Ltd., July 15, 2005" and "Dispersion technology centered on suspension (solid / liquid dispersion system) and industrial. Practical application The process and disperser described in Paragraph No.
- JP-A-2015-157893 "Comprehensive Data Collection, Published by Management Development Center Publishing Department, October 10, 1978" can be preferably used.
- the particles may be miniaturized in the salt milling step.
- the materials, equipment, processing conditions, etc. used in the salt milling step for example, the descriptions in JP-A-2015-194521 and JP-A-2012-046629 can be referred to.
- any filter that has been conventionally used for filtration or the like can be used without particular limitation.
- a fluororesin such as polytetrafluoroethylene (PTFE), a polyamide resin such as nylon (for example, nylon-6, nylon-6,6), and a polyolefin resin such as polyethylene and polypropylene (PP) (high density, ultrahigh molecular weight).
- PP polypropylene
- the pore size of the filter is preferably 0.01 to 7.0 ⁇ m, more preferably 0.01 to 3.0 ⁇ m, and even more preferably 0.05 to 0.5 ⁇ m. If the pore size of the filter is within the above range, fine foreign matter can be removed more reliably.
- the nominal value of the filter manufacturer can be referred to.
- various filters provided by Nippon Pole Co., Ltd. (DFA4201NIEY, etc.), Advantech Toyo Co., Ltd., Japan Integris Co., Ltd. (formerly Nippon Microlith Co., Ltd.), KITZ Microfilter Co., Ltd., etc. can be used.
- a fibrous filter medium As the filter.
- the fibrous filter medium include polypropylene fiber, nylon fiber, glass fiber and the like.
- examples of commercially available products include SBP type series (SBP008, etc.), TPR type series (TPR002, TPR005, etc.) and SHPX type series (SHPX003, etc.) manufactured by Roki Techno Co., Ltd.
- filters different filters (eg, first filter and second filter, etc.) may be combined. At that time, the filtration with each filter may be performed only once or twice or more. Further, filters having different pore diameters may be combined within the above-mentioned range. Further, the filtration with the first filter may be performed only on the dispersion liquid, and after mixing the other components, the filtration may be performed with the second filter.
- the film of the present invention is a film obtained from the above-mentioned coloring composition of the present invention.
- the film of the present invention can be used for an optical filter such as a color filter or an infrared transmission filter.
- the film thickness of the film of the present invention can be appropriately adjusted according to the purpose.
- the film thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and even more preferably 5 ⁇ m or less.
- the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and 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 hue of green, red, blue, cyan, magenta or yellow, and more preferably has a hue of green, red or yellow. preferable. Further, the film of the present invention can be preferably used as a colored pixel of a color filter. Examples of the colored pixel include a red pixel, a green pixel, a blue pixel, a magenta color pixel, a cyan color pixel, a yellow pixel and the like, and are preferably a red pixel, a green pixel and a yellow pixel, and are a red pixel or a green pixel. It is more preferable, and it is further preferable that the number of green pixels is large.
- the wavelength at which the light transmittance is 50% preferably exists in the wavelength range of 470 to 520 nm, more preferably exists in the wavelength range of 475 to 520 nm, and 480 to 520 nm. It is more preferred to be in the wavelength range. Among them, it is preferable that the wavelength at which the light transmittance is 50% exists in each of the wavelength range of 470 to 520 nm and the wavelength range of 575 to 625 nm. In this embodiment, the wavelength on the short wavelength side where the light transmittance is 50% preferably exists in the wavelength range of 475 to 520 nm, and more preferably exists in the wavelength range of 480 to 520 nm.
- the wavelength on the long wavelength side where the light transmittance is 50% preferably exists in the wavelength range of 580 to 620 nm, and more preferably exists in the wavelength range of 585 to 615 nm.
- a film having such spectral characteristics is preferably used as a green pixel.
- the film of the present invention preferably has, for example, any of the following spectral characteristics (1) to (4).
- the maximum value of the light transmittance in the film thickness direction in the wavelength range of 400 to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmittance in the film thickness direction.
- the minimum value of the rate in the wavelength range of 800 to 1300 nm is 70% or more (preferably 75% or more, more preferably 80% or more).
- a film having such spectral characteristics can block light in the wavelength range of 400 to 640 nm and transmit light having a wavelength of more than 700 nm.
- the maximum value of the light transmittance in the film thickness direction in the wavelength range of 400 to 750 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmittance in the film thickness direction.
- a film having such spectral characteristics can block light in the wavelength range of 400 to 750 nm and transmit light having a wavelength of more than 850 nm.
- the maximum value of the light transmittance in the film thickness direction in the wavelength range of 400 to 830 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmittance in the film thickness direction.
- a film having such spectral characteristics can block light in the wavelength range of 400 to 830 nm and transmit light having a wavelength exceeding 940 nm.
- the maximum value of the light transmittance in the film thickness direction in the wavelength range of 400 to 950 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the light transmittance in the film thickness direction.
- a film having such spectral characteristics can block light in the wavelength range of 400 to 950 nm and transmit light having a wavelength of more than 1040 nm.
- the film of the present invention can be produced through a step of applying the coloring composition of the present invention.
- the film manufacturing method preferably further includes a step of forming a pattern (pixel). Examples of the pattern (pixel) forming method include a photolithography method and a dry etching method, and the photolithography method is preferable.
- Pattern formation by the photolithography method includes a step of forming a coloring composition layer on a support using the coloring composition of the present invention, a step of exposing the coloring composition layer in a pattern, and a step of exposing the coloring composition layer in a pattern. It is preferable to include a step of developing and removing the exposed portion to form a pattern (pixel). If necessary, a step of baking the coloring composition layer (pre-baking step) and a step of baking the developed pattern (pixels) (post-baking step) may be provided.
- the coloring composition layer of the present invention is used to form the coloring composition layer on the support.
- the support is not particularly limited and may be appropriately selected depending on the intended use.
- a glass substrate, a silicon substrate, and the like can be mentioned, and a silicon substrate is preferable.
- a charge-coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, or the like may be formed on the silicon substrate.
- CMOS complementary metal oxide semiconductor
- a black matrix that isolates each pixel may be formed on the silicon substrate.
- the silicon substrate may be provided with a base layer for improving the adhesion with the upper layer, preventing the diffusion of substances, or flattening the surface of the substrate.
- the base layer may be formed by using a composition obtained by removing a colorant from the coloring composition described in the present specification, a composition containing a curable compound, a surfactant or the like described in the present specification, or the like.
- the surface contact angle of the base layer is preferably 20 to 70 ° when measured with diiodomethane. Further, it is preferably 30 to 80 ° when measured with water. When the surface contact angle of the base layer is within the above range, the coating property of the resin composition is good.
- the surface contact angle of the base layer can be adjusted by, for example, adding a surfactant.
- a known method can be used as a method for applying the coloring composition.
- a drop method drop cast
- a slit coating method for example, a spray method; a roll coating method; a rotary coating method (spin coating); a casting coating method; a slit and spin method; a pre-wet method (for example, JP-A-2009-145395).
- Inkjet for example, on-demand method, piezo method, thermal method
- ejection system printing such as nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, metal mask printing method, etc.
- Various printing methods transfer method using a mold or the like; nanoimprint method and the like.
- the method of application to inkjet is not particularly limited, and is, for example, the method shown in "Expandable and usable inkjet-infinite possibilities seen in patents-, published in February 2005, Sumi Betechno Research" (especially from page 115). (Page 133), and the methods described in JP-A-2003-262716, JP-A-2003-185831, JP-A-2003-261827, JP-A-2012-126830, JP-A-2006-169325, and the like. Can be mentioned. Further, regarding the method of applying the coloring composition, the description of International Publication No. 2017/030174 and International Publication No. 2017/018419 can be referred to, and these contents are incorporated in the present specification.
- the colored composition layer formed on the support may be dried (prebaked).
- the prebaking temperature is preferably 150 ° C. or lower, more preferably 120 ° C. or lower, and even more preferably 110 ° C. or lower.
- the lower limit can be, for example, 50 ° C. or higher, or 80 ° C. or higher.
- the prebaking time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, and even more preferably 80 to 220 seconds. Pre-baking can be performed on a hot plate, an oven, or the like.
- the colored composition layer is exposed in a pattern (exposure step).
- the colored composition layer can be exposed in a pattern by exposing the colored composition layer through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. As a result, the exposed portion can be cured.
- Examples of radiation (light) that can be used for exposure include g-line and i-line. Further, light having a wavelength of 300 nm or less (preferably light having a wavelength of 180 to 300 nm) can also be used. Examples of the light having a wavelength of 300 nm or less include KrF line (wavelength 248 nm) and ArF line (wavelength 193 nm), and KrF line (wavelength 248 nm) is preferable. Further, a long wave light source having a diameter of 300 nm or more can also be used.
- pulse exposure is an exposure method of a method of repeatedly irradiating and pausing light in a cycle of a short time (for example, a millisecond level or less).
- Irradiation dose for example, preferably 0.03 ⁇ 2.5J / cm 2, more preferably 0.05 ⁇ 1.0J / cm 2.
- the oxygen concentration at the time of exposure can be appropriately selected, and in addition to the operation in the atmosphere, for example, in a low oxygen atmosphere having an oxygen concentration of 19% by volume or less (for example, 15% by volume, 5% by volume, or substantially). It may be exposed in an oxygen-free environment (for example, 22% by volume, 30% by volume, or 50% by volume) in a high oxygen atmosphere having an oxygen concentration of more than 21% by volume.
- the exposure illuminance can be set as appropriate, and is usually selected from the range of 1000 W / m 2 to 100,000 W / m 2 (for example, 5000 W / m 2 , 15,000 W / m 2 , or 35,000 W / m 2). Can be done. Oxygen concentration and exposure illuminance may appropriately combined conditions, for example, illuminance 10000 W / m 2 at an oxygen concentration of 10 vol%, oxygen concentration of 35 vol% can be such illuminance 20000W / m 2.
- the unexposed portion of the coloring composition layer is developed and removed to form a pattern (pixel).
- the unexposed portion of the coloring composition layer can be developed and removed using a developing solution.
- the colored composition layer of the unexposed portion in the exposure step is eluted in the developing solution, and only the photocured portion remains.
- the temperature of the developing solution is preferably, for example, 20 to 30 ° C.
- the development time is preferably 20 to 180 seconds. Further, in order to improve the residue removability, the steps of shaking off the developing solution every 60 seconds and further supplying a new developing solution may be repeated several times.
- Examples of the developing solution include organic solvents and alkaline developing solutions, and alkaline developing solutions are preferably used.
- the alkaline developer an alkaline aqueous solution (alkaline developer) obtained by diluting an alkaline agent with pure water is preferable.
- the alkaline agent include ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxyamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetrabutylammonium hydroxide.
- Ethyltrimethylammonium hydroxide Ethyltrimethylammonium hydroxide, benzyltrimethylammonium hydroxide, dimethylbis (2-hydroxyethyl) ammonium hydroxide, choline, pyrrole, piperidine, 1,8-diazabicyclo- [5.4.0] -7-undecene, etc.
- examples thereof include organic alkaline compounds and inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogencarbonate, sodium silicate and sodium metasilicate.
- the alkaline agent a compound having a large molecular weight is preferable in terms of environment and safety.
- the concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass.
- the developer may further contain a surfactant.
- the developer may be once produced as a concentrated solution and diluted to a concentration required for use from the viewpoint of convenience of transfer and storage.
- the dilution ratio is not particularly limited, but can be set in the range of, for example, 1.5 to 100 times. It is also preferable to wash (rinse) with pure water after development. Further, it is preferable that the rinsing is performed by supplying the rinsing liquid to the developed colored composition layer while rotating the support on which the developed colored composition layer is formed.
- the nozzle for discharging the rinse liquid from the central portion of the support it is also preferable to move the nozzle for discharging the rinse liquid from the central portion of the support to the peripheral edge of the support.
- the nozzle may be moved while gradually reducing the moving speed.
- Additional exposure treatment and post-baking are post-development curing treatments to complete the curing.
- the heating temperature in the post-bake is, for example, preferably 100 to 240 ° C, more preferably 200 to 240 ° C.
- Post-baking can be performed on the developed film in a continuous or batch manner using a heating means such as a hot plate, a convection oven (hot air circulation dryer), or a high-frequency heater so as to meet the above conditions. ..
- the light used for the exposure is preferably light having a wavelength of 400 nm or less. Further, the additional exposure process may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
- Pattern formation by the dry etching method includes a step of forming a colored composition layer on a support using the colored composition of the present invention and curing the entire colored composition layer to form a cured product layer.
- the optical filter of the present invention has the above-mentioned film of the present invention.
- Examples of the type of optical filter include a color filter and an infrared transmission filter, and a color filter is preferable.
- As the color filter it is preferable to have the film of the present invention as the colored pixels of the color filter.
- the optical filter may be provided with a protective layer on the surface of the film of the present invention.
- a protective layer By providing the protective layer, various functions such as oxygen blocking, low reflection, hydrophobicization, and shielding of light of a specific wavelength (ultraviolet rays, near infrared rays, etc.) can be imparted.
- the thickness of the protective layer is preferably 0.01 to 10 ⁇ m, more preferably 0.1 to 5 ⁇ m.
- Examples of the method for forming the protective layer include a method of applying a resin composition dissolved in an organic solvent to form the protective layer, a chemical vapor deposition method, and a method of attaching the molded resin with an adhesive.
- the components constituting the protective layer include (meth) acrylic resin, en-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, and polyimide.
- Resin polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, urethane resin, aramid resin, polyamide resin, alkyd resin, epoxy resin, modified silicone resin, fluorine Examples thereof include resins, polycarbonate resins, polyacrylonitrile resins, cellulose resins, Si, C, W, Al 2 O 3 , Mo, SiO 2 , and Si 2 N 4, and two or more of these components may be contained.
- the protective layer preferably contains a polyol resin, SiO 2 , and Si 2 N 4 .
- the protective layer preferably contains a (meth) acrylic resin and a fluororesin.
- the resin composition When the resin composition is applied to form the protective layer, a known method such as a spin coating method, a casting method, a screen printing method, or an inkjet method can be used as the application method of the resin composition.
- a known method such as a spin coating method, a casting method, a screen printing method, or an inkjet method can be used as the application method of the resin composition.
- a known organic solvent for example, propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.
- the protective layer is formed by a chemical vapor deposition method
- the chemical vapor deposition method is a known chemical vapor deposition method (thermochemical vapor deposition method, plasma chemical vapor deposition method, photochemical vapor deposition method). Can be used.
- the protective layer may be an additive such as organic / inorganic fine particles, an absorber for light of a specific wavelength (for example, ultraviolet rays, near infrared rays, etc.), a refractive index adjuster, an antioxidant, an adhesive, a surfactant, etc., if necessary. May be contained.
- organic / inorganic fine particles include polymer fine particles (for example, silicone resin fine particles, polystyrene fine particles, melamine resin fine particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, and titanium oxynitride. , Magnesium fluoride, hollow silica, silica, calcium carbonate, barium sulfate and the like.
- a known absorbent can be used as the light absorber of a specific wavelength.
- the content of these additives can be adjusted as appropriate, but is preferably 0.1 to 70% by mass, more preferably 1 to 60% by mass, based on the total mass of the protective layer
- the protective layer described in paragraphs 0073 to 0092 of JP-A-2017-151176 can also be used.
- the optical filter may have a structure in which each pixel is embedded in a space partitioned by a partition wall, for example, in a grid pattern.
- the solid-state image sensor of the present invention has the above-mentioned film of the present invention.
- the configuration of the solid-state image sensor is not particularly limited as long as it includes the film of the present invention and functions as a solid-state image sensor, and examples thereof include the following configurations.
- a solid-state image sensor CCD (charge-coupled device) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.
- a transfer electrode made of polysilicon or the like.
- the configuration has a color filter on the device protective film.
- the color filter may have a structure in which each colored pixel is embedded in a space partitioned by a partition wall, for example, in a grid pattern.
- the partition wall preferably has a low refractive index for each colored pixel. Examples of the image pickup apparatus having such a structure include the apparatus described in JP-A-2012-227478, JP-A-2014-179557, and International Publication No. 2018/043654.
- an ultraviolet absorbing layer may be provided in the structure of the solid-state image sensor to improve the light resistance.
- the image pickup device provided with the solid-state image pickup device of the present invention can be used not only for digital cameras and electronic devices having an image pickup function (mobile phones and the like), but also for in-vehicle cameras and surveillance cameras.
- the image display device of the present invention has the above-mentioned film of the present invention.
- the image display device include a liquid crystal display device and an organic electroluminescence display device.
- the liquid crystal display device is described in, for example, “Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, Kogyo Chosakai Co., Ltd., published in 1994)”.
- the liquid crystal display device to which the present invention can be applied is not particularly limited, and for example, it can be applied to various types of liquid crystal display devices described in the above-mentioned "next-generation liquid crystal display technology".
- Green colorant PG36: C.I. I. Pigment Green 36 (phthalocyanine compound, green pigment)
- PG58 C.I. I. Pigment Green 58 (phthalocyanine compound, green pigment)
- PG62 C.I. I. Pigment Green 62 (phthalocyanine compound, green pigment)
- PR254 C.I. I. Pigment Red 254 (diketopyrrolopyrrole compound, red pigment)
- PR264 C.I. I. Pigment Red 264 (diketopyrrolopyrrole compound, red pigment)
- PR272 C.I. I. Pigment Red 272 (diketopyrrolopyrrole compound, red pigment)
- Azomethine metal complex 1 C.I. I. Pigment Yellow 129 (azomethine copper complex, compound with the following structure, yellow pigment) Azomethine metal complex 2 Azomethine metal complex 3 A 1: 1 solid solution of azomethine metal complex 1 (CI Pigment Yellow 129) and azomethine metal complex 2.
- PY138 C.I. I. Pigment Yellow 138 (quinophthalone compound, yellow pigment)
- PY139 C.I. I. Pigment Yellow 139 (isoindoline compound, yellow pigment)
- PY150 C.I. I. Pigment Yellow 150 (azo compound, yellow pigment)
- PY185 C.I. I. Pigment Yellow 185 (isoindoline compound, yellow pigment)
- PY215 C.I. I. Pigment Yellow 215 (Pteridine compound, yellow pigment)
- Pigment derivative 1 Compound with the following structure
- B-2 A resin solution of resin B-2 synthesized by the following method (PGMEA solution having a solid content concentration of 30% by mass).
- a resin solution of resin B-3 synthesized by the following method (PGMEA solution having a solid content concentration of 30% by mass).
- the acid value was 43 mgKOH / g and the weight average molecular weight was 9000 as follows, except that 20 parts by mass of t-butyl methacrylate was changed to (3-ethyloxetane-3-yl) methyl methacrylate.
- a resin solution of structural resin B-3 was obtained.
- solvent 1 Propylene glycol monomethyl ether acetate (PGMEA)
- Resin 2 After charging 70.0 parts by mass of cyclohexanone into a separable 4-neck flask equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, a dropping tube and a stirrer, raising the temperature to 80 ° C., and replacing the inside of the flask with nitrogen.
- Polymerizable compound 1 A compound having the following structure
- Polymerizable compound 2 A mixture of compounds having the following structure (a mixture of a left compound (bifunctional (meth) acrylate compound) and a right compound (pentofunctional (meth) acrylate compound) having a molar ratio of 7: 3).
- Photopolymerization initiator Photopolymerization initiator 1: Compound with the following structure
- Epoxy compound 1 Epoxy compound 1: EHPE3150 (manufactured by Daicel Corporation)
- the colored composition layer was paddle-developed at 23 ° C. for 60 seconds. Then, rinsing with a spin shower and washing with pure water were carried out, and further, the first pixels were formed on the glass wafer by heating (post-baking) at 200 ° C. for 5 minutes using a hot plate. Subsequently, using the radiation-sensitive composition described in paragraph No. 0231 of JP2013-254847A, development and exposure are performed in the same manner as in the first pixel formation, and the first pixel on the glass wafer is subjected to development and exposure.
- TMAH tetramethylammonium hydroxide
- a second pixel (transparent pixel) was formed in the missing portion of the Bayer pattern.
- the transmittance (initial spectroscopy) of light having a wavelength of 400 to 700 nm of the second pixel was measured using a microscopic photophotometer (“OSP-SP200” manufactured by Olympus Optical Co., Ltd.).
- OSP-SP200 microscopic photophotometer
- the glass wafer on which the first pixel and the second pixel were formed was allowed to stand for 1500 hours under the conditions of a temperature of 85 ° C. and a relative humidity of 85% to perform a reliability test, and then a microspectrophotometer.
- ⁇ T max1 is 0.5% or less 4: ⁇ T max1 is greater than 0.5% and 1% or less 3: ⁇ T max1 is greater than 1% and 3% or less 2: ⁇ T max1 is greater than 3% and 5% Below 1: ⁇ T max1 is greater than 5%
- the coloring composition described in the above table is applied onto an 8-inch (20.32 cm) glass wafer by a spin coating method so as to have a post-baking ratio of 0.65 ⁇ m, and then heated at 100 ° C. for 2 minutes using a hot plate. A colored composition layer was formed. Next, the colored composition layer was exposed with an exposure amount of 300 mJ / cm 2 using an i-line stepper exposure apparatus FPA-3000i5 + (manufactured by Canon Inc.). Then, using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH), the composition layer was paddle-developed at 23 ° C. for 60 seconds.
- TMAH tetramethylammonium hydroxide
- rinsing with a spin shower and washing with pure water were carried out, and further, a film was formed by heating (post-baking) at 200 ° C. for 5 minutes using a hot plate.
- the transmittance of the obtained membrane was measured using MCPD3700 (manufactured by Otsuka Electronics Co., Ltd.).
- the above film was irradiated with light for 1500 hours at an illuminance of 100,000 lux using a super xenon weather meter SX75 (manufactured by Suga Test Instruments Co., Ltd.) to perform a light resistance test.
- the maximum value ( ⁇ T max2 ) of the amount of change in transmittance was obtained, and the light resistance was evaluated according to the following criteria. The smaller the value of ⁇ T max2, the better the light resistance.
- ⁇ T max2 is 5% or less 4: ⁇ T max2 is greater than 5% and 10% or less 3: ⁇ T max2 is greater than 10% and 20% or less 2: ⁇ T max2 is greater than 20% and 25% or less 1: ⁇ T max2 is greater than 25% and less than 30% 0: ⁇ T max2 is greater than 30%
- the table below shows the evaluation results of long-term reliability and light resistance.
- the content of the yellow colorant in the colorant used for each coloring composition (yellow colorant ratio in the table) and the content of the azomethine metal complex in the yellow colorant (azomethine metal complex ratio in the table) are also included. I will write it.
- the coloring compositions of Examples 1 to 28 and 32 to 40 are applied onto an 8-inch (20.32 cm) glass wafer by a spin coating method, and then heated at 100 ° C. for 2 minutes using a hot plate, and then. For a film having a thickness of 0.65 ⁇ m formed by heating at 200 ° C.
- the transmittance of light having a wavelength of 470 to 520 nm was measured, and the value of the wavelength at which the transmittance was 50% was set in the table below. It is described in the column of "transmittance 50% wavelength (nm)".
- the coloring composition of the example was able to form a film having excellent long-term reliability.
- Example 1001 The green coloring composition was applied onto the silicon wafer by a spin coating method so that the film thickness after film formation was 1.0 ⁇ m. Then, using a hot plate, it was heated at 100 ° C. for 2 minutes. Next, using an i-line stepper exposure apparatus FPA-3000i5 + (manufactured by Canon Inc.) , exposure was performed with an exposure amount of 1000 mJ / cm 2 through a mask with a dot pattern of 2 ⁇ m square. Then, paddle development was carried out at 23 ° C. for 60 seconds using a 0.3% by mass aqueous solution of tetramethylammonium hydroxide (TMAH). Then, it was rinsed with a spin shower and further washed with pure water.
- TMAH tetramethylammonium hydroxide
- the green coloring composition was patterned to form green pixels by heating at 200 ° C. for 5 minutes using a hot plate.
- the red coloring composition and the blue coloring composition were patterned by the same process to sequentially form red pixels and blue pixels to form a color filter having green pixels, red pixels and blue pixels.
- green pixels are formed in a Bayer pattern, and red pixels and blue pixels are formed in an island pattern in an adjacent region thereof.
- the obtained color filter was incorporated into a solid-state image sensor according to a known method. This solid-state image sensor had a suitable image recognition ability.
- the green coloring composition the coloring composition of Example 2 was used.
- the red coloring composition the coloring composition of Example 29 was used.
- the blue coloring composition will be described later.
- the raw materials used to prepare the blue coloring composition are as follows.
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Abstract
Description
<1> 黄色着色剤を含む着色剤と、樹脂と、溶剤とを含む着色組成物であって、
上記着色剤中における黄色着色剤の含有量が30質量%以上であり、
上記黄色着色剤は、アゾメチン金属錯体を15質量%以上含む、着色組成物。
<2> 上記黄色着色剤中におけるキノフタロン化合物の含有量が50質量%未満である、<1>に記載の着色組成物。
<3> 上記アゾメチン金属錯体は、アゾメチン銅錯体およびアゾメチン亜鉛錯体から選ばれる少なくとも1種を含む、<1>または<2>に記載の着色組成物。
<4> 上記着色剤は、緑色着色剤及び赤色着色剤から選ばれる少なくとも1種を含む、<1>~<3>のいずれか1つに記載の着色組成物。
<5> 上記着色剤は、緑色着色剤を含み、上記緑色着色剤はフタロシアニン化合物を含む、<1>~<4>のいずれか1つに記載の着色組成物。
<6> 上記着色組成物を用いて厚さ0.65μmの膜を形成した際に、上記膜の光透過率が50%となる波長が、470~520nmの波長範囲に存在する、<1>~<5>のいずれか1つに記載の着色組成物。
<7> 更に、重合性化合物と光重合開始剤とを含む、<1>~<6>のいずれか1つに記載の着色組成物。
<8> カラーフィルタ用または赤外線透過フィルタ用である、<1>~<7>のいずれか1つに記載の着色組成物。
<9> <1>~<8>のいずれか1つに記載の着色組成物から得られる膜。
<10> <9>に記載の膜を有する光学フィルタ。
<11> <9>に記載の膜を有する固体撮像素子。
<12> <9>に記載の膜を有する画像表示装置。
本明細書において、「~」とはその前後に記載される数値を下限値および上限値として含む意味で使用される。
本明細書における基(原子団)の表記において、置換および無置換を記していない表記は、置換基を有さない基(原子団)と共に置換基を有する基(原子団)をも包含する。例えば、「アルキル基」とは、置換基を有さないアルキル基(無置換アルキル基)のみならず、置換基を有するアルキル基(置換アルキル基)をも包含する。
本明細書において「露光」とは、特に断らない限り、光を用いた露光のみならず、電子線、イオンビーム等の粒子線を用いた描画も露光に含める。また、露光に用いられる光としては、水銀灯の輝線スペクトル、エキシマレーザに代表される遠紫外線、極紫外線(EUV光)、X線、電子線等の活性光線または放射線が挙げられる。
本明細書において、「(メタ)アクリレート」は、アクリレートおよびメタクリレートの双方、または、いずれかを表し、「(メタ)アクリル」は、アクリルおよびメタクリルの双方、または、いずれかを表し、「(メタ)アクリロイル」は、アクリロイルおよびメタクリロイルの双方、または、いずれかを表す。
本明細書において、構造式中のMeはメチル基を表し、Etはエチル基を表し、Buはブチル基を表し、Phはフェニル基を表す。
本明細書において、重量平均分子量および数平均分子量は、GPC(ゲルパーミエーションクロマトグラフィ)法により測定したポリスチレン換算値である。
本明細書において、全固形分とは、組成物の全成分から溶剤を除いた成分の総質量をいう。
本明細書において、顔料とは、溶剤に対して溶解しにくい化合物を意味する。
本明細書において「工程」との語は、独立した工程だけではなく、他の工程と明確に区別できない場合であってもその工程の所期の作用が達成されれば、本用語に含まれる。
本発明の着色組成物は、
黄色着色剤を含む着色剤と、樹脂と、溶剤とを含む着色組成物であって、
着色剤中における黄色着色剤の含有量が30質量%以上であり、
黄色着色剤は、アゾメチン金属錯体を15質量%以上含むことを特徴とする。
本発明の着色組成物は、黄色着色剤を含む着色剤を含有する。黄色着色剤としては、アゾメチン金属錯体を含有するものが用いられる。
X1およびX2が表すアルコキシ基としては、メトキシ基、エトキシ基、プロピルオキシ基、i-プロピルオキシ基、ブチルオキシ基、i-ブチルオキシ基、s-ブチルオキシ基、t-ブチルオキシ基、ペンチルオキシ基、1-メチルブチルオキシ基、2-メチルブチルオキシ基、3-メチルブチルオキシ基、1,1-ジメチルプロピルオキシ基、1,2-ジメチルプロピルオキシ基、2,2-ジメチルプロピルオキシ基、1-エチルプロピルオキシ基、ヘキシルオキシ基、1-メチルペンチルオキシ基、2-メチルペンチルオキシ基、3-メチルペンチルオキシ基、4-メチルペンチルオキシ基、1,1-ジメチルブチルオキシ基、1,2-ジメチルブチルオキシ基、1,3-ジメチルブチルオキシ基、2,2-ジメチルブチルオキシ基、2,3-ジメチルブチルオキシ基、3,3-ジメチルブチルオキシ基、1-エチルブチルオキシ基、2-エチルブチルオキシ基、1,1,2-トリメチルプロピルオキシ基、1,2,2-トリメチルプロピルオキシ基、1-エチル-1-メチルプロピルオキシ基、1-エチル-2-メチルプロピルオキシ基などが挙げられる。なかでも、炭素数1~8のアルコキシ基が好適な例として挙げられる。
(1)赤色着色剤と青色着色剤と黄色着色剤とを含有する態様。
(2)赤色着色剤と青色着色剤と黄色着色剤と紫色着色剤とを含有する態様。
(3)赤色着色剤と青色着色剤と黄色着色剤と紫色着色剤と緑色着色剤とを含有する態様。
(4)赤色着色剤と青色着色剤と黄色着色剤と緑色着色剤とを含有する態様。
(5)黄色着色剤と紫色着色剤とを含有する態様。
また、アゾメチン金属錯体の含有量は、緑色着色剤の100質量部に対して3質量部以上であることが好ましく、5質量部以上であることがより好ましく、10質量部以上であることが更に好ましい。
また、アゾメチン金属錯体の含有量は、フタロシアニン化合物の100質量部に対して3質量部以上であることが好ましく、5質量部以上であることがより好ましく、10質量部以上であることが更に好ましい。
また、アゾメチン金属錯体の含有量は、赤色着色剤の100質量部に対して3質量部以上であることが好ましく、5質量部以上であることがより好ましく、10質量部以上であることが更に好ましい。
また、アゾメチン金属錯体の含有量は、ジケトピロロピロール化合物の100質量部に対して3質量部以上であることが好ましく、5質量部以上であることがより好ましく、10質量部以上であることが更に好ましい。
本発明の着色組成物は樹脂を含有する。樹脂は、例えば、顔料等を着色組成物中で分散させる用途や、バインダーの用途で配合される。なお、主に顔料等を着色組成物中で分散させるために用いられる樹脂を分散剤ともいう。ただし、樹脂のこのような用途は一例であって、このような用途以外を目的として樹脂を使用することもできる。
式(a-2)中、Ra11は、水素原子、ヒドロキシ基、アルキル基、アルコキシ基、アリール基、アリールオキシ基、アシル基またはオキシラジカルを表し、Ra12~Ra19は、それぞれ独立して、水素原子、アルキル基またはアリール基を表す。
式(Ac-2)中、Ar10は芳香族カルボキシル基を含む基を表し、L11は、-COO-または-CONH-を表し、L12は3価の連結基を表し、P10はポリマー鎖を表す。
式(Ar-12)中、n2は1~8の整数を表し、1~4の整数であることが好ましく、1または2であることがより好ましく、2であることが更に好ましい。
式(Ar-13)中、n3およびn4はそれぞれ独立して0~4の整数を表し、0~2の整数であることが好ましく、1または2であることがより好ましく、1であることが更に好ましい。ただし、n3およびn4の少なくとも一方は1以上の整数である。
式(Ar-13)中、Q1は、単結合、-O-、-CO-、-COOCH2CH2OCO-、-SO2-、-C(CF3)2-、上記式(Q-1)で表される基または上記式(Q-2)で表される基を表す。
本発明の着色組成物は、溶剤を含有する。溶剤としては、有機溶剤が挙げられる。溶剤の種類は、各成分の溶解性や組成物の塗布性を満足すれば基本的には特に制限はない。有機溶剤としては、エステル系溶剤、ケトン系溶剤、アルコール系溶剤、アミド系溶剤、エーテル系溶剤、炭化水素系溶剤などが挙げられる。これらの詳細については、国際公開第2015/166779号の段落番号0223を参酌でき、この内容は本明細書に組み込まれる。また、環状アルキル基が置換したエステル系溶剤、環状アルキル基が置換したケトン系溶剤も好ましく用いることもできる。有機溶剤の具体例としては、ポリエチレングリコールモノメチルエーテル、ジクロロメタン、3-エトキシプロピオン酸メチル、3-エトキシプロピオン酸エチル、エチルセロソルブアセテート、乳酸エチル、ジエチレングリコールジメチルエーテル、酢酸ブチル、3-メトキシプロピオン酸メチル、2-ヘプタノン、シクロヘキサノン、酢酸シクロヘキシル、シクロペンタノン、エチルカルビトールアセテート、ブチルカルビトールアセテート、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、3-メトキシ-N,N-ジメチルプロパンアミド、3-ブトキシ-N,N-ジメチルプロパンアミドなどが挙げられる。ただし有機溶剤としての芳香族炭化水素類(ベンゼン、トルエン、キシレン、エチルベンゼン等)は、環境面等の理由により低減したほうがよい場合がある(例えば、有機溶剤全量に対して、50質量ppm(parts per million)以下とすることもでき、10質量ppm以下とすることもでき、1質量ppm以下とすることもできる)。
本発明の着色組成物は、顔料誘導体を含有することができる。顔料誘導体としては、色素骨格に酸基または塩基性基が結合した構造を有する化合物が挙げられる。顔料誘導体を構成する色素骨格としては、キノリン色素骨格、ベンゾイミダゾロン色素骨格、ベンゾイソインドール色素骨格、ベンゾチアゾール色素骨格、イニミウム色素骨格、スクアリリウム色素骨格、クロコニウム色素骨格、オキソノール色素骨格、ピロロピロール色素骨格、ジケトピロロピロール色素骨格、アゾ色素骨格、アゾメチン色素骨格、フタロシアニン色素骨格、ナフタロシアニン色素骨格、アントラキノン色素骨格、キナクリドン色素骨格、ジオキサジン色素骨格、ペリノン色素骨格、ペリレン色素骨格、チオインジゴ色素骨格、イソインドリン色素骨格、イソインドリノン色素骨格、キノフタロン色素骨格、イミニウム色素骨格、ジチオール色素骨格、トリアリールメタン色素骨格、ピロメテン色素骨格等が挙げられる。酸基としては、スルホ基、カルボキシル基、リン酸基及びこれらの塩が挙げられる。塩を構成する原子または原子団としては、アルカリ金属イオン(Li+、Na+、K+など)、アルカリ土類金属イオン(Ca2+、Mg2+など)、アンモニウムイオン、イミダゾリウムイオン、ピリジニウムイオン、ホスホニウムイオンなどが挙げられる。塩基性基としては、アミノ基、ピリジニル基およびその塩、アンモニウム基の塩、並びにフタルイミドメチル基が挙げられる。塩を構成する原子または原子団としては、水酸化物イオン、ハロゲンイオン、カルボン酸イオン、スルホン酸イオン、フェノキシドイオンなどが挙げられる。
本発明の着色組成物は、赤外線吸収剤をさらに含有することができる。例えば、本発明の着色組成物を用いて赤外線透過フィルタを形成する場合においては、着色組成物中に赤外線吸収剤を含有させることで得られる膜について透過させる光の波長をより長波長側にシフトさせることができる。赤外線吸収剤は、極大吸収波長を波長700nmよりも長波長側に有する化合物であることが好ましい。赤外線吸収剤は波長700nmを超え1800nm以下の範囲に極大吸収波長を有する化合物であることが好ましい。また、赤外線吸収剤の波長500nmにおける吸光度A1と極大吸収波長における吸光度A2との比率A1/A2は、0.08以下であることが好ましく、0.04以下であることがより好ましい。
本発明の着色組成物は、重合性化合物を含有することができる。重合性化合物としては、ラジカル、酸または熱により架橋可能な公知の化合物を用いることができる。本発明において、重合性化合物は、例えば、エチレン性不飽和結合含有基を有する化合物であることが好ましい。エチレン性不飽和結合含有基としては、ビニル基、(メタ)アリル基、(メタ)アクリロイル基などが挙げられる。本発明で用いられる重合性化合物は、ラジカル重合性化合物であることが好ましい。
本発明の着色組成物は光重合開始剤を含有することができる。光重合開始剤としては、特に制限はなく、公知の光重合開始剤の中から適宜選択することができる。例えば、紫外線領域から可視領域の光線に対して感光性を有する化合物が好ましい。光重合開始剤は、光ラジカル重合開始剤であることが好ましい。
本発明の着色組成物は、環状エーテル基を有する化合物を含有することができる。環状エーテル基としては、エポキシ基、オキセタニル基などが挙げられる。環状エーテル基を有する化合物は、エポキシ基を有する化合物(以下、エポキシ化合物ともいう)であることが好ましい。エポキシ化合物としては、特開2013-011869号公報の段落番号0034~0036、特開2014-043556号公報の段落番号0147~0156、特開2014-089408号公報の段落番号0085~0092に記載された化合物、特開2017-179172号公報に記載された化合物を用いることもできる。これらの内容は、本明細書に組み込まれる。
本発明の着色組成物は、硬化促進剤を含んでもよい。硬化促進剤としては、チオール化合物、メチロール化合物、アミン化合物、ホスホニウム塩化合物、アミジン塩化合物、アミド化合物、塩基発生剤、イソシアネート化合物、アルコキシシラン化合物、オニウム塩化合物などが挙げられる。硬化促進剤の具体例としては、国際公開第2018/056189号の段落番号0094~0097に記載の化合物、特開2015-034963号公報の段落番号0246~0253に記載の化合物、特開2013-041165号公報の段落番号0186~0251に記載の化合物、特開2014-055114号公報に記載のイオン性化合物、特開2012-150180号公報の段落番号0071~0080に記載の化合物、特開2011-253054号公報に記載のエポキシ基を有するアルコキシシラン化合物、特許第5765059号公報の段落番号0085~0092に記載の化合物、特開2017-036379号公報に記載のカルボキシル基含有エポキシ硬化剤などが挙げられる。硬化促進剤を含有する場合、着色組成物の全固形分中における硬化促進剤の含有量は0.3~8.9質量%が好ましく、0.8~6.4質量%がより好ましい。
本発明の着色組成物は、紫外線吸収剤を含有することができる。紫外線吸収剤は、共役ジエン化合物、アミノジエン化合物、サリシレート化合物、ベンゾフェノン化合物、ベンゾトリアゾール化合物、アクリロニトリル化合物、ヒドロキシフェニルトリアジン化合物、インドール化合物、トリアジン化合物などを用いることができる。このような化合物としては、特開2009-217221号公報の段落番号0038~0052、特開2012-208374号公報の段落番号0052~0072、特開2013-068814号公報の段落番号0317~0334、特開2016-162946号公報の段落番号0061~0080に記載された化合物が挙げられ、これらの内容は本明細書に組み込まれる。紫外線吸収剤の具体例としては、下記構造の化合物などが挙げられる。紫外線吸収剤の市販品としては、例えば、UV-503(大東化学(株)製)などが挙げられる。また、ベンゾトリアゾール化合物としては、ミヨシ油脂製のMYUAシリーズ(化学工業日報、2016年2月1日)が挙げられる。また、紫外線吸収剤は、特許第6268967号公報の段落番号0049~0059に記載された化合物を用いることもできる。
本発明の着色組成物は、重合禁止剤を含有することができる。重合禁止剤としては、ハイドロキノン、p-メトキシフェノール、ジ-tert-ブチル-p-クレゾール、ピロガロール、tert-ブチルカテコール、ベンゾキノン、4,4’-チオビス(3-メチル-6-tert-ブチルフェノール)、2,2’-メチレンビス(4-メチル-6-t-ブチルフェノール)、N-ニトロソフェニルヒドロキシアミン塩(アンモニウム塩、第一セリウム塩等)が挙げられる。中でも、p-メトキシフェノールが好ましい。重合禁止剤を含有する場合、着色組成物の全固形分中における重合禁止剤の含有量は、0.0001~5質量%が好ましい。重合禁止剤は、1種類のみでもよく、2種類以上でもよい。2種類以上の場合は、合計量が上記範囲となることが好ましい。
本発明の着色組成物は、シランカップリング剤を含有することができる。本発明において、シランカップリング剤は、加水分解性基とそれ以外の官能基とを有するシラン化合物を意味する。また、加水分解性基とは、ケイ素原子に直結し、加水分解反応及び縮合反応の少なくともいずれかによってシロキサン結合を生じ得る置換基をいう。加水分解性基としては、例えば、ハロゲン原子、アルコキシ基、アシルオキシ基などが挙げられ、アルコキシ基が好ましい。すなわち、シランカップリング剤は、アルコキシシリル基を有する化合物が好ましい。また、加水分解性基以外の官能基としては、例えば、ビニル基、(メタ)アリル基、(メタ)アクリロイル基、メルカプト基、エポキシ基、オキセタニル基、アミノ基、ウレイド基、スルフィド基、イソシアネート基、フェニル基などが挙げられ、アミノ基、(メタ)アクリロイル基およびエポキシ基が好ましい。シランカップリング剤の具体例としては、N-β-アミノエチル-γ-アミノプロピルメチルジメトキシシラン(信越化学工業(株)製、商品名 KBM-602)、N-β-アミノエチル-γ-アミノプロピルトリメトキシシラン(信越化学工業(株)製、商品名 KBM-603)、N-β-アミノエチル-γ-アミノプロピルトリエトキシシラン(信越化学工業(株)製、商品名 KBE-602)、γ-アミノプロピルトリメトキシシラン(信越化学工業(株)製、商品名 KBM-903)、γ-アミノプロピルトリエトキシシラン(信越化学工業(株)製、商品名 KBE-903)、3-メタクリロキシプロピルメチルジメトキシシラン(信越化学工業(株)製、商品名 KBM-502)、3-メタクリロキシプロピルトリメトキシシラン(信越化学工業(株)製、商品名 KBM-503)等がある。また、シランカップリング剤の具体例については、特開2009-288703号公報の段落番号0018~0036に記載の化合物、特開2009-242604号公報の段落番号0056~0066に記載の化合物が挙げられ、これらの内容は本明細書に組み込まれる。シランカップリング剤を含有する場合、着色組成物の全固形分中におけるシランカップリング剤の含有量は、0.01~15.0質量%が好ましく、0.05~10.0質量%がより好ましい。シランカップリング剤は、1種類のみでもよく、2種類以上でもよい。2種類以上の場合は、合計量が上記範囲となることが好ましい。
本発明の着色組成物は、界面活性剤を含有することができる。界面活性剤としては、フッ素系界面活性剤、ノニオン系界面活性剤、カチオン系界面活性剤、アニオン系界面活性剤、シリコーン系界面活性剤などの各種界面活性剤を使用することができる。界面活性剤については、国際公開第2015/166779号の段落番号0238~0245に記載された界面活性剤が挙げられ、この内容は本明細書に組み込まれる。
本発明の着色組成物は、酸化防止剤を含有することができる。酸化防止剤としては、フェノール化合物、亜リン酸エステル化合物、チオエーテル化合物などが挙げられる。フェノール化合物としては、フェノール系酸化防止剤として知られる任意のフェノール化合物を使用することができる。好ましいフェノール化合物としては、ヒンダードフェノール化合物が挙げられる。フェノール性ヒドロキシ基に隣接する部位(オルト位)に置換基を有する化合物が好ましい。前述の置換基としては炭素数1~22の置換又は無置換のアルキル基が好ましい。また、酸化防止剤は、同一分子内にフェノール基と亜リン酸エステル基を有する化合物も好ましい。また、酸化防止剤は、リン系酸化防止剤も好適に使用することができる。着色組成物の全固形分中における酸化防止剤の含有量は、0.01~20質量%であることが好ましく、0.3~15質量%であることがより好ましい。酸化防止剤を含有する場合、酸化防止剤は1種のみを用いてもよく、2種以上を用いてもよい。2種以上を用いる場合は、合計量が上記範囲となることが好ましい。
本発明の着色組成物は、必要に応じて、増感剤、硬化促進剤、フィラー、熱硬化促進剤、可塑剤及びその他の助剤類(例えば、導電性粒子、充填剤、消泡剤、難燃剤、レベリング剤、剥離促進剤、香料、表面張力調整剤、連鎖移動剤など)を含有してもよい。これらの成分を適宜含有させることにより、膜物性などの性質を調整することができる。これらの成分は、例えば、特開2012-003225号公報の段落番号0183以降(対応する米国特許出願公開第2013/0034812号明細書の段落番号0237)の記載、特開2008-250074号公報の段落番号0101~0104、0107~0109等の記載を参酌でき、これらの内容は本明細書に組み込まれる。また、本発明の着色組成物は、必要に応じて、潜在酸化防止剤を含有してもよい。潜在酸化防止剤としては、酸化防止剤として機能する部位が保護基で保護された化合物であって、100~250℃で加熱するか、又は酸/塩基触媒存在下で80~200℃で加熱することにより保護基が脱離して酸化防止剤として機能する化合物が挙げられる。潜在酸化防止剤としては、国際公開第2014/021023号、国際公開第2017/030005号、特開2017-008219号公報に記載された化合物が挙げられる。潜在酸化防止剤の市販品としては、アデカアークルズGPA-5001((株)ADEKA製)等が挙げられる。また、特開2018-155881号公報に記載されているように、C.I.ピグメントイエロー129を耐候性改良の目的で添加しても良い。
本発明の着色組成物は、前述の成分を混合して調製できる。着色組成物の調製に際しては、全成分を同時に溶剤に溶解および/または分散して着色組成物を調製してもよいし、必要に応じて、各成分を適宜2つ以上の溶液または分散液としておいて、使用時(塗布時)にこれらを混合して着色組成物を調製してもよい。
本発明の膜は、上述した本発明の着色組成物から得られる膜である。本発明の膜は、カラーフィルタや赤外線透過フィルタなどの光学フィルタに用いることができる。
(1):膜の厚み方向における光透過率の、波長400~640nmの範囲における最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)で、膜の厚み方向における光透過率の、波長800~1300nmの範囲における最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)である。このような分光特性を有する膜は、波長400~640nmの範囲の光を遮光して、波長700nmを超える光を透過させることができる。
(2):膜の厚み方向における光透過率の、波長400~750nmの範囲における最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)で、膜の厚み方向における光透過率の、波長900~1300nmの範囲における最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)である膜。このような分光特性を有する膜は、波長400~750nmの範囲の光を遮光して、波長850nmを超える光を透過させることができる。
(3):膜の厚み方向における光透過率の、波長400~830nmの範囲における最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)で、膜の厚み方向における光透過率の、波長1000~1300nmの範囲における最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)である膜。このような分光特性を有する膜は、波長400~830nmの範囲の光を遮光して、波長940nmを超える光を透過させることができる。
(4):膜の厚み方向における光透過率の、波長400~950nmの範囲における最大値が20%以下(好ましくは15%以下、より好ましくは10%以下)で、膜の厚み方向における光透過率の、波長1100~1300nmの範囲における最小値が70%以上(好ましくは75%以上、より好ましくは80%以上)である膜。このような分光特性を有する膜は、波長400~950nmの範囲の光を遮光して、波長1040nmを超える光を透過させることができる。
次に、本発明の膜の製造方法について説明する。本発明の膜は、本発明の着色組成物を塗布する工程を経て製造できる。膜の製造方法においては、更にパターン(画素)を形成する工程を含むことが好ましい。パターン(画素)の形成方法としては、フォトリソグラフィ法、ドライエッチング法が挙げられ、フォトリソグラフィ法が好ましい。
本発明の光学フィルタは、上述した本発明の膜を有する。光学フィルタの種類としては、カラーフィルタおよび赤外線透過フィルタが挙げられ、カラーフィルタであることが好ましい。カラーフィルタとしては、カラーフィルタの着色画素として本発明の膜を有することが好ましい。
本発明の固体撮像素子は、上述した本発明の膜を有する。固体撮像素子の構成としては、本発明の膜を備え、固体撮像素子として機能する構成であれば特に限定はないが、例えば、以下のような構成が挙げられる。
本発明の画像表示装置は、上述した本発明の膜を有する。画像表示装置としては、液晶表示装置や有機エレクトロルミネッセンス表示装置などが挙げられる。画像表示装置の定義や各画像表示装置の詳細については、例えば「電子ディスプレイデバイス(佐々木昭夫著、(株)工業調査会、1990年発行)」、「ディスプレイデバイス(伊吹順章著、産業図書(株)平成元年発行)」などに記載されている。また、液晶表示装置については、例えば「次世代液晶ディスプレイ技術(内田龍男編集、(株)工業調査会、1994年発行)」に記載されている。本発明が適用できる液晶表示装置に特に制限はなく、例えば、上記の「次世代液晶ディスプレイ技術」に記載されている色々な方式の液晶表示装置に適用できる。
下記表に記載の原料を混合した混合液を、ビーズミル(ジルコニアビーズ0.1mm径)を用いて3時間混合および分散した。次いで、減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて圧力2000kg/cm3および流量500g/minの条件の下、分散処理を行なった。この分散処理を全10回繰り返して、分散液を得た。下記表に記載の配合量を示す数値は質量部である。下記表に、着色剤中における黄色着色剤の含有量(表中の黄色着色剤比)、黄色着色剤中におけるアゾメチン金属錯体の含有量(表中のアゾメチン金属錯体比)も併せて記す。
PG36:C.I.ピグメントグリーン36(フタロシアニン化合物、緑色顔料)
PG58:C.I.ピグメントグリーン58(フタロシアニン化合物、緑色顔料)
PG62:C.I.ピグメントグリーン62(フタロシアニン化合物、緑色顔料)
PR254:C.I.ピグメントレッド254(ジケトピロロピロール化合物、赤色顔料)
PR264:C.I.ピグメントレッド264(ジケトピロロピロール化合物、赤色顔料)
PR272:C.I.ピグメントレッド272(ジケトピロロピロール化合物、赤色顔料)
アゾメチン金属錯体1:C.I.ピグメントイエロー129(アゾメチン銅錯体、下記構造の化合物、黄色顔料)
アゾメチン金属錯体1(C.I.ピグメントイエロー129)とアゾメチン金属錯体2の1:1の固溶体。
PY139:C.I.ピグメントイエロー139(イソインドリン化合物、黄色顔料)
PY150:C.I.ピグメントイエロー150(アゾ化合物、黄色顔料)
PY185:C.I.ピグメントイエロー185(イソインドリン化合物、黄色顔料)
PY215:C.I.ピグメントイエロー215(プテリジン化合物、黄色顔料)
B-1:下記構造の樹脂(固形分濃度30%のプロピレングリコールモノメチルエーテルアセテート(PGMEA)溶液、主鎖に付記した数値は質量比であり、側鎖に付記した数値は繰り返し単位の数である。重量平均分子量=13000、酸価65mgKOH/g)
メチルメタクリレート50質量部、n-ブチルメタクリレート30質量部、t-ブチルメタクリレート20質量部、PGMEA45.4質量部を反応容器に仕込み、雰囲気ガスを窒素ガスで置換した。反応容器内を70℃に加熱して、3-メルカプト-1,2-プロパンジオール6質量部を添加して、さらにAIBN(アゾビスイソブチロニトリル)0.12質量部を加え、12時間反応させた。固形分測定により95%が反応したことを確認した。次に、ピロメリット酸無水物9.7質量部、PGMEA70.3質量部、触媒としてDBU(1,8-ジアザビシクロ-[5.4.0]-7-ウンデセン)0.20質量部を追加し、120℃で7時間反応させた。酸価の測定で98%以上の酸無水物がハーフエステル化していることを確認し反応を終了した。PGMEAを加えて不揮発分(固形分濃度)を30質量%に調整し、酸価43mgKOH/g、重量平均分子量9000の下記構造の樹脂B-2の樹脂溶液を得た。
樹脂B-2の合成において、t-ブチルメタクリレート20質量部を、(3-エチルオキセタン-3-イル)メチルメタクリレートに変更した以外は同様にして、酸価43mgKOH/g、重量平均分子量9000の下記構造の樹脂B-3の樹脂溶液を得た。
溶剤1:プロピレングリコールモノメチルエーテルアセテート(PGMEA)
下記の表に記載の原料を混合して、着色組成物を製造した。
分散液1~35、c1:上述した分散液1~35、c1
重合性化合物1:下記構造の化合物
エポキシ化合物1:EHPE3150((株)ダイセル製)
溶剤1:PGMEA
溶剤2:シクロヘキサノン
[長期信頼性評価]
上記表に記載の着色組成物を8インチ(20.32cm)のガラスウエハ上にポストベーク後0.65μmとなるようにスピンコート法で塗布した後、ホットプレートを用いて100℃で2分間加熱して、着色組成物層を形成した。次いで、i線ステッパー露光装置FPA-3000i5+(Canon(株)製)を用い、ベイヤーパターンを有するマスクを介して、300mJ/cm2の露光量で上記着色組成物層を露光した。次いで、水酸化テトラメチルアンモニウム(TMAH)0.3質量%水溶液を用い、着色組成物層に対し23℃で60秒間パドル現像を行った。その後、スピンシャワーによるリンス、純水を用いた水洗を実施し、さらに、ホットプレートを用いて200℃で5分間加熱(ポストベーク)して、ガラスウエハ上に第1の画素を形成した。続いて特開2013-254047号公報の段落番号0231に記載の感放射線性組成物を使用し、第1の画素形成と同様の方法にて現像および露光を行い、ガラスウエハ上の第1の画素のベイヤーパターンの抜け部に、第2の画素(透明画素)を形成した。顕微分光光度計(オリンパス光学社製「OSP-SP200」)を用いて、第2の画素の波長400~700nmの光の透過率(初期分光)を測定した。
次に、第1の画素と第2の画素とをそれぞれ形成したガラスウエハを温度85℃、相対湿度85%の条件下で1500時間静置して信頼性試験を行った後、顕微分光光度計(オリンパス光学社製「OSP-SP200」)を用いて、第1の画素との境界から2μm離れた位置における第2の画素の波長400~700nmの光の透過率(信頼性試験後の分光)を測定した。
試験前後の第2の画素の波長400~700nmの光の透過率の変化量(=|信頼性試験前の第2の画素の透過率(%)-信頼性試験後の第2の画素の透過率(%)|)を算出して透過率の変化量の最大値(ΔTmax1)を求め、下記の基準で長期信頼性を評価した。ΔTmax1の値が小さいほど、長期信頼性に優れていることを意味する。
5:ΔTmax1が0.5%以下
4:ΔTmax1が0.5%より大きく、1%以下
3:ΔTmax1が1%より大きく、3%以下
2:ΔTmax1が3%より大きく、5%以下
1:ΔTmax1が5%より大きい
上記表に記載の着色組成物を8インチ(20.32cm)のガラスウエハ上にポストベーク後0.65μmとなるようにスピンコート法で塗布した後、ホットプレートを用いて100℃で2分間加熱して、着色組成物層を形成した。次いで、i線ステッパー露光装置FPA-3000i5+(Canon(株)製)を用い、300mJ/cm2の露光量で着色組成物層を露光した。次いで、水酸化テトラメチルアンモニウム(TMAH)0.3質量%水溶液を用い、組成物層に対し23℃で60秒間パドル現像を行った。その後、スピンシャワーによるリンス、純水を用いた水洗を実施し、さらに、ホットプレートを用いて200℃で5分間加熱(ポストベーク)して、膜を形成した。得られた膜の透過率を、MCPD3700(大塚電子(株)製)を用いて測定した。
上記膜に対し、スーパーキセノンウェーザーメーターSX75(スガ試験機製)を用いて照度10万luxで1500時間光を照射して耐光性試験を行った。耐光性試験の膜の透過率を、MCPD3700(大塚電子(株)製)を用いて測定した。
試験前後の膜の波長400~700nmの光の透過率の変化量(=|耐光性試験前の膜の透過率(%)-耐光性試験後の膜の透過率(%)|)を算出して透過率の変化量の最大値(ΔTmax2)を求め、下記の基準で耐光性を評価した。ΔTmax2の値が小さいほど、耐光性に優れていることを意味する。
5:ΔTmax2が5%以下
4:ΔTmax2が5%より大きく、10%以下
3:ΔTmax2が10%より大きく、20%以下
2:ΔTmax2が20%より大きく、25%以下
1:ΔTmax2が25%より大きく、30%以下
0:ΔTmax2が30%より大きい
シリコンウエハ上に、緑色着色組成物を製膜後の膜厚が1.0μmになるようにスピンコート法で塗布した。次いで、ホットプレートを用いて、100℃で2分間加熱した。次いで、i線ステッパー露光装置FPA-3000i5+(キヤノン(株)製)を用い、1000mJ/cm2の露光量で2μm四方のドットパターンのマスクを介して露光した。次いで、水酸化テトラメチルアンモニウム(TMAH)0.3質量%水溶液を用い、23℃で60秒間パドル現像を行った。その後、スピンシャワーにてリンスを行い、更に純水にて水洗した。次いで、ホットプレートを用いて、200℃で5分間加熱することで、緑色着色組成物をパターニングして緑色画素を形成した。同様に赤色着色組成物、青色着色組成物を同様のプロセスでパターニングして、赤色画素、青色画素を順次形成して、緑色画素、赤色画素および青色画素を有するカラーフィルタを形成した。このカラーフィルタにおいては、緑色画素がベイヤーパターンで形成されており、その隣接する領域に、赤色画素、青色画素がアイランドパターンで形成されている。得られたカラーフィルタを公知の方法に従い固体撮像素子に組み込んだ。この固体撮像素子は好適な画像認識能を有していた。なお、緑色着色組成物としては、実施例2の着色組成物を使用した。赤色着色組成物としては、実施例29の着色組成物を使用した。青色着色組成物については後述する。
下記成分を混合し、撹拌した後、孔径0.45μmのナイロン製フィルタ(日本ポール(株)製)でろ過して、青色着色組成物を調製した。
青色顔料分散液:30.47質量部
染料1:2.64質量部
樹脂1:0.01質量部
樹脂3:0.04質量部
重合性化合物3:1.56質量部
光重合開始剤4:0.57質量部
添加剤1:0.35質量部
エポキシ化合物2:0.46質量部
界面活性剤101:2.00質量部(1質量%PGMEA溶液として)
PGMEA:5.70質量部
シクロヘキサノン:55.4質量部
プロピレングリコールモノメチルエーテル:0.8質量部
C.I.ピグメントブルー15:6を15質量部、分散剤(Disperbyk-161、BYKChemie社製)2.2質量部、樹脂3 2.2質量部、溶剤1 80.6質量部からなる混合液を、ビーズミル(ジルコニアビーズ0.3mm径)により3時間混合及び分散した。その後更に、減圧機構付き高圧分散機NANO-3000-10(日本ビーイーイー(株)製)を用いて、2000kg/cm2の圧力下で流量500g/minとして分散処理を行た。この分散処理を10回繰り返し、青色顔料分散液を得た。
Claims (12)
- 黄色着色剤を含む着色剤と、樹脂と、溶剤とを含む着色組成物であって、
前記着色剤中における黄色着色剤の含有量が30質量%以上であり、
前記黄色着色剤は、アゾメチン金属錯体を15質量%以上含む、着色組成物。 - 前記黄色着色剤中におけるキノフタロン化合物の含有量が50質量%未満である、請求項1に記載の着色組成物。
- 前記アゾメチン金属錯体は、アゾメチン銅錯体およびアゾメチン亜鉛錯体から選ばれる少なくとも1種を含む、請求項1または2に記載の着色組成物。
- 前記着色剤は、緑色着色剤及び赤色着色剤から選ばれる少なくとも1種を含む、請求項1~3のいずれか1項に記載の着色組成物。
- 前記着色剤は、緑色着色剤を含み、前記緑色着色剤はフタロシアニン化合物を含む、請求項1~4のいずれか1項に記載の着色組成物。
- 前記着色組成物を用いて厚さ0.65μmの膜を形成した際に、前記膜の光透過率が50%となる波長が、470~520nmの波長範囲に存在する、請求項1~5のいずれか1項に記載の着色組成物。
- 更に、重合性化合物と光重合開始剤とを含む、請求項1~6のいずれか1項に記載の着色組成物。
- カラーフィルタ用または赤外線透過フィルタ用である、請求項1~7のいずれか1項に記載の着色組成物。
- 請求項1~8のいずれか1項に記載の着色組成物から得られる膜。
- 請求項9に記載の膜を有する光学フィルタ。
- 請求項9に記載の膜を有する固体撮像素子。
- 請求項9に記載の膜を有する画像表示装置。
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JP7425198B2 (ja) | 2020-06-15 | 2024-01-30 | 富士フイルム株式会社 | 着色組成物、膜、カラーフィルタ、固体撮像素子及び画像表示装置 |
WO2024018910A1 (ja) * | 2022-07-19 | 2024-01-25 | 富士フイルム株式会社 | 着色組成物、膜、光学フィルタ、固体撮像素子、画像表示装置および着色剤 |
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