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
  • 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
• • 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
  • C09B19/00—Oxazine 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
  • C09B57/00—Other synthetic dyes of known constitution
• • 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
  • C09B57/00—Other synthetic dyes of known constitution
  • C09B57/10—Metal complexes of organic compounds not being dyes in uncomplexed form
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/006—Preparation of organic pigments
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B5/00—Optical elements other than lenses
  • G02B5/20—Filters
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
  • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10F—INORGANIC SEMICONDUCTOR DEVICES SENSITIVE TO INFRARED RADIATION, LIGHT, ELECTROMAGNETIC RADIATION OF SHORTER WAVELENGTH OR CORPUSCULAR RADIATION
  • H10F39/00—Integrated devices, or assemblies of multiple devices, comprising at least one element covered by group H10F30/00, e.g. radiation detectors comprising photodiode arrays
  • H10F39/80—Constructional details of image sensors
  • H10F39/805—Coatings
  • H10F39/8053—Colour filters

Definitions

• the present invention relates to a coloring composition containing a phthalocyanine mixed crystal pigment.
• the present invention also relates to a film, an optical filter, a solid-state imaging device, and an image display device that use the coloring composition.
• Color filters are used as key devices in displays and optical elements. Color filters usually have pixels of the three primary colors, red, green, and blue, and serve to separate transmitted light into the three primary colors.
• the colored pixels of each color of the color filter are manufactured using a coloring composition containing a colorant.
• a coloring composition for forming blue pixels contains a phthalocyanine pigment such as Color Index Pigment Blue 15:6 as a colorant.
• Patent Document 1 describes a coloring composition that contains a colorant containing Color Index Pigment Blue 15:6, a resin, a photopolymerization initiator, and a polymerizable compound.
• an object of the present invention is to provide a coloring composition capable of forming pixels in which the generation of development residues is suppressed.
• Another object of the present invention is to provide a film, an optical filter, a solid-state imaging device, and an image display device.
• the present invention provides the following:
• a coloring composition comprising a colorant, a resin, a photopolymerization initiator, and a polymerizable compound,
• the colorant is a coloring composition containing a phthalocyanine mixed crystal pigment which is a mixed crystal of two or more kinds of phthalocyanines.
• a phthalocyanine mixed crystal pigment which is a mixed crystal of two or more kinds of phthalocyanines.
• the phthalocyanine mixed crystal pigment is a mixed crystal of two or more kinds of phthalocyanines that differ only in the type of the central metal.
• the phthalocyanine mixed crystal pigment is a mixed crystal of two or more kinds of unsubstituted phthalocyanines that differ only in the type of the central metal.
• ⁇ 4> The colored composition according to any one of ⁇ 1> to ⁇ 3>, wherein the two or more kinds of phthalocyanines include zinc phthalocyanine.
• ⁇ 5> The coloring composition according to any one of ⁇ 1> to ⁇ 4>, wherein the phthalocyanine mixed crystal pigment has an average primary particle size of 3 to 200 nm.
• ⁇ 6> The colored composition according to any one of ⁇ 1> to ⁇ 5>, in which the content of the phthalocyanine mixed crystal pigment in the colorant is 50 mass% or more.
• ⁇ 7> The colored composition according to any one of ⁇ 1> to ⁇ 6>, wherein the colorant further contains an oxazine compound.
• ⁇ 8> The coloring composition according to any one of ⁇ 1> to ⁇ 7>, wherein the colorant further contains at least one dye selected from the group consisting of xanthene dyes and pyrromethene dyes.
• ⁇ 9> A film obtained by using the colored composition according to any one of ⁇ 1> to ⁇ 8>.
• ⁇ 10> An optical filter having the film according to ⁇ 9>.
• ⁇ 11> A solid-state imaging device comprising the film according to ⁇ 9>.
• ⁇ 12> An image display device having the film according to ⁇ 9>.
• the present invention can provide a coloring composition capable of forming pixels in which the generation of development residues is suppressed.
• the present invention can also provide a film, an optical filter, a solid-state imaging device, and an image display device.
• alkyl group encompasses not only alkyl groups that have no substituents (unsubstituted alkyl groups) but also alkyl groups that have substituents (substituted alkyl groups).
• exposure includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams.
• Examples of light used for exposure include the bright line spectrum of a mercury lamp, far ultraviolet light represented by an excimer laser, extreme ultraviolet light (EUV light), X-rays, active rays or radiation such as electron beams.
• (meth)acrylate refers to both or either of acrylate and methacrylate
• (meth)acrylic refers to both or either of acrylic and methacrylic
• (meth)acryloyl refers to both or either of acryloyl and methacryloyl.
• Me represents a methyl group
• Et represents an ethyl group
• Bu represents a butyl group
• Ph represents a phenyl group.
• the weight average molecular weight and number average molecular weight are values calculated as polystyrene standards measured by GPC (gel permeation chromatography).
• the total solids content refers to the total mass of all components of the composition excluding the solvent.
• a pigment means a compound that is poorly soluble in a solvent.
• the term "process” refers not only to an independent process, but also to a process that cannot be clearly distinguished from other processes, as long as the intended effect of the process is achieved.
• the coloring composition of the present invention is a coloring composition comprising a colorant, a resin, a photopolymerization initiator, and a polymerizable compound,
• the colorant is characterized by containing a phthalocyanine mixed crystal pigment which is a mixed crystal of two or more kinds of phthalocyanines.
• the coloring composition of the present invention has good developability, and can suppress the occurrence of development residues between pixels when forming pixels by a photolithography method.
• the reason why such an effect is obtained is presumed to be as follows.
• the coloring composition of the present invention uses a colorant containing a phthalocyanine mixed crystal pigment, which is a mixed crystal of two or more kinds of phthalocyanines. It is presumed that the use of the phthalocyanine mixed crystal pigment as a colorant has good dispersibility, and therefore can suppress the generation of pigment aggregates that are difficult to develop, and can suppress the generation of development residues.
• the above-mentioned phthalocyanine mixed crystal pigment has good dispersibility in the coloring composition, and the coloring composition of the present invention also has excellent storage stability. Therefore, the occurrence of viscosity variation can be suppressed even after long-term storage.
• the coloring composition of the present invention can be preferably used as a coloring composition for optical filters.
• optical filters include color filters and infrared transmission filters. That is, the coloring composition of the present invention is preferably used as a coloring composition for color filters or infrared transmission filters, and is more preferably used as a coloring composition for color filters. More specifically, it can be preferably used as a coloring composition for forming pixels of color filters or a coloring composition for forming infrared transmission filters.
• the above phthalocyanine mixed crystal pigment is presumed to be due to strong absorption in the wavelength range of 600 to 700 nm caused by the interaction in the excited state between different phthalocyanine molecules, and has high transmittance in the vicinity of a wavelength of 450 nm, excellent light blocking properties in the wavelength range of 600 to 700 nm, and has spectral characteristics preferable as a blue pigment.
• the coloring composition of the present invention can be particularly preferably used as a coloring composition for forming blue pixels of a color filter.
• the transmittance at a wavelength of 400 nm in the thickness direction of the film is preferably 45% or more, more preferably 50% or more, and even more preferably 55% or more.
• the transmittance of the film at a wavelength of 450 nm is preferably 70% or more, more preferably 75% or more, and even more preferably 80% or more.
• the minimum transmittance of the film in the wavelength range of 400 to 500 nm is preferably 30% or more, more preferably 35% or more, and even more preferably 40% or more.
• the maximum transmittance of the film in the wavelength range of 600 to 700 nm is preferably less than 5%, and more preferably less than 3%.
• a film having such spectral characteristics can be preferably used as a blue pixel of a color filter.
• the film used to measure the transmittance is preferably a film obtained by applying a coloring composition onto a glass substrate by a method such as spin coating, drying the film at 100°C for 2 minutes using a hot plate or the like, heating the film at 200°C for 5 minutes using a hot plate or the like, and then allowing it to cool to room temperature.
• the transmittance can be measured using a conventionally known spectrophotometer.
• the coloring composition of the present invention contains a colorant.
• the colorant contained in the coloring composition of the present invention is a phthalocyanine mixed crystal pigment that is a mixed crystal of two or more types of phthalocyanines.
• a mixed crystal is also called a solid solution, and refers to a mixture of two or more compounds (here, phthalocyanines) that are dissolved in each other and form a uniform solid phase, and is different from a simple mixture of the two or more compounds.
• Methods for producing mixed crystals are disclosed, for example, in JP-A-60-035055 and JP-A-02-038463. Whether or not two or more phthalocyanines form a mixed crystal can be easily verified by thermogravimetric analysis or the like. When two or more phthalocyanine pigments are simply mixed, the thermal decomposition temperature of each phthalocyanine pigment is obtained. When two or more phthalocyanines form a mixed crystal, a thermal decomposition temperature different from the thermal decomposition temperature of each phthalocyanine is obtained.
• the phthalocyanine mixed crystal pigment may be partially amorphous.
• the phthalocyanine mixed crystal pigment is preferably a blue pigment.
• a blue pigment is a pigment that has low absorption intensity in the wavelength range of 400 to 500 nm and high absorption intensity in the wavelength range of 500 to 700 nm.
• the absorption intensity at a wavelength of 400 nm is preferably less than 0.3, more preferably 0.25 or less, and even more preferably 0.2 or less.
• the maximum value of the absorption intensity in the wavelength range of 400 to 500 nm is preferably 0.3 or less, more preferably 0.25 or less, and even more preferably 0.2 or less.
• the wavelength at which the absorption intensity shows 0.5 is preferably in the wavelength range of 600 to 650 nm, more preferably in the wavelength range of 585 to 675 nm, and even more preferably in the wavelength range of 570 to 700 nm.
• Phthalocyanine mixed crystal pigments having such spectral characteristics are preferably used as blue pigments.
• the phthalocyanine used in the phthalocyanine mixed crystal pigment includes a compound represented by the formula (1).
• M 1 represents a metal atom
• X 1 to X 8 each independently represent ⁇ N—, ⁇ CR X1 — or ⁇ CH—, R X1 representing a substituent
• Examples of the metal atom represented by M1 include copper, zinc, cobalt, manganese, iron, nickel, magnesium, aluminum, vanadium and titanium atoms, and copper or zinc atoms are preferred because they significantly enhance the effects of the present invention. These metal atoms may be coordinated with a ligand.
• Examples of the ligand include oxo ligands, halogen ligands and phosphate ester ligands.
• Examples of the substituent represented by R and R include the groups exemplified as the substituent T described later, and are preferably a halogen atom, an alkyl group, an aryl group, an alkoxy group, an alkylthio group, an alkylsulfonyl group, an acyl group, an alkoxycarbonyl group, an acyloxy group, a carbamoyl group, or a sulfamoyl group, and more preferably a halogen atom or an alkyl group.
• the halogen atom includes a fluorine atom, a chlorine atom, and a bromine atom, and is preferably a fluorine atom.
• the number of carbon atoms in the alkyl group is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
• the alkyl group may have a substituent. Examples of the substituent include a halogen atom, an alkyl group, an aryl group, an alkoxy group, an alkylthio group, an alkylsulfonyl group, an acyl group, an alkoxycarbonyl group, an acyloxy group, a carbamoyl group, and a sulfamoyl group.
• the number of carbon atoms in the aryl group is preferably 6 to 20, more preferably 6 to 12, and even more preferably 6.
• the aryl group may have a substituent.
• substituents include a halogen atom, an alkyl group, an aryl group, an alkoxy group, an alkylthio group, an alkylsulfonyl group, an acyl group, an alkoxycarbonyl group, an acyloxy group, a carbamoyl group, and a sulfamoyl group.
• the number of carbon atoms in the alkoxy group, alkylthio group, alkylsulfonyl group, sulfamoyl group and carbamoyl group is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
• These groups may further have a substituent.
• the substituent include a halogen atom, an alkyl group, an aryl group, an alkoxy group, an alkylthio group, an alkylsulfonyl group, an acyl group, an alkoxycarbonyl group, an acyloxy group, a carbamoyl group and a sulfamoyl group.
• the number of carbon atoms in the acyl group, alkoxycarbonyl group and acyloxy group is preferably 2 to 10, more preferably 2 to 5, and even more preferably 2 to 3.
• These groups may further have a substituent.
• the substituent include a halogen atom, an alkyl group, an aryl group, an alkoxy group, an alkylthio group, an alkylsulfonyl group, an acyl group, an alkoxycarbonyl group, an acyloxy group, a carbamoyl group and a sulfamoyl group.
• X 1 to X 8 each independently preferably represent ⁇ CR X1 — or ⁇ CH—, more preferably ⁇ CH—.
• Y 1 to Y 8 each independently preferably represent ⁇ CR Y1 — or ⁇ CH—, and more preferably represent ⁇ CH—.
• substituent T examples include the following groups: halogen atoms (e.g., fluorine atoms, chlorine atoms, bromine atoms, iodine atoms), alkyl groups (preferably alkyl groups having 1 to 30 carbon atoms), alkenyl groups (preferably alkenyl groups having 2 to 30 carbon atoms), alkynyl groups (preferably alkynyl groups having 2 to 30 carbon atoms), aryl groups (preferably aryl groups having 6 to 30 carbon atoms), heteroaryl groups (preferably heteroaryl groups having 1 to 30 carbon atoms), amino groups (preferably amino groups having 0 to 30 carbon atoms), alkoxy groups (preferably alkoxy groups having 1 to 30 carbon atoms), aryloxy groups (preferably aryloxy groups having 6 to 30 carbon atoms), heteroaryloxy groups (preferably heteroaryloxy groups having 1 to 30 carbon atoms), acyl groups (preferably acyl groups having 2 to 30 carbon atoms), alkoxycarbonyl groups (
• M represents a copper atom, a zinc atom, a cobalt atom, a manganese atom, an iron atom, a nickel atom, or a magnesium atom.
• the phthalocyanine mixed crystal pigment is preferably a mixed crystal of two or more phthalocyanines differing only in the type of central metal, because this provides excellent suitability for the production of the mixed crystal pigment.
• the mixed crystal pigment is a mixed crystal of two or more unsubstituted phthalocyanines differing only in the type of central metal, because this provides excellent thermal stability of the mixed crystal pigment.
• the mixed crystal of the above compound Pc001-M which is a compound in which M is a copper atom and a compound in which M is a zinc atom, corresponds to a mixed crystal of two or more unsubstituted phthalocyanines differing only in the type of central metal.
• the unsubstituted phthalocyanine is preferably the above compound Pc001-M.
• the phthalocyanine used in the phthalocyanine mixed crystal pigment preferably contains zinc phthalocyanine, and more preferably contains unsubstituted zinc phthalocyanine. According to this embodiment, the color value can be further improved.
• the zinc phthalocyanine is a phthalocyanine having a zinc atom as the central atom, and is preferably a compound in which M 1 in the above formula (1) is a zinc atom.
• the phthalocyanine mixed crystal pigment is preferably a mixed crystal of zinc phthalocyanine and a phthalocyanine having a metal atom other than zinc as the central atom (also called other phthalocyanine).
• the other phthalocyanine include copper phthalocyanine, cobalt phthalocyanine, nickel phthalocyanine, manganese phthalocyanine, and iron phthalocyanine. At least one selected from copper phthalocyanine and cobalt phthalocyanine is preferable, and copper phthalocyanine is more preferable, because it can further improve light resistance.
• the ratio of zinc phthalocyanine to other phthalocyanine is preferably 10 to 1000 parts by mass of the other phthalocyanine per 100 parts by mass of zinc phthalocyanine, more preferably 20 to 500 parts by mass, and even more preferably 33 to 300 parts by mass.
• a preferred embodiment of the phthalocyanine mixed crystal pigment is a mixed crystal of two types of phthalocyanines, which is preferred in terms of having better heat resistance.
• Another preferred embodiment of the phthalocyanine mixed crystal pigment is a mixed crystal of three or more (preferably 3 to 5, more preferably 3 to 4) phthalocyanines. Such a phthalocyanine mixed crystal pigment is preferred in that it has better dispersion stability.
• the average primary particle diameter of the phthalocyanine mixed crystal pigment is preferably 3 to 200 nm.
• the lower limit is preferably 5 nm or more, and more preferably 10 nm or more.
• the upper limit is preferably 150 nm or less, and more preferably 100 nm or less.
• the primary particle diameter of the pigment can be determined from a photograph obtained by observing the primary particles of the pigment with a transmission electron microscope. Specifically, the projected area of the primary particles of the pigment is determined, and the corresponding circle equivalent diameter is calculated as the primary particle diameter of the pigment.
• the average primary particle diameter in the present invention is the arithmetic mean value of the primary particle diameters of 400 primary particles of the pigment.
• the primary particles of the pigment refer to independent particles that are not aggregated.
• the amount of lithium, sodium, potassium and calcium ions contained in the phthalocyanine mixed crystal pigment is preferably 1000 ppm or less, more preferably 100 ppm or less, and particularly preferably 10 ppm or less.
• the content of the above metal ions can be measured by inductively coupled plasma optical emission spectroscopy (ICP-OES).
• the colorant contained in the coloring composition of the present invention may further contain a colorant other than the above-mentioned phthalocyanine mixed crystal pigment (hereinafter, also referred to as other colorant).
• a colorant other than the above-mentioned phthalocyanine mixed crystal pigment hereinafter, also referred to as other colorant.
• the other colorant to be used in combination include a green colorant, a red colorant, a yellow colorant, a purple colorant, a blue colorant, an orange colorant, etc., and it is preferable that the other colorant is at least one selected from the purple colorant and the blue colorant, and it is more preferable that the other colorant is a purple colorant.
• the other colorants may be pigments or dyes.
• the pigments may be either inorganic or organic pigments, but organic pigments are preferred from the standpoint of color variation, ease of dispersion, safety, etc.
• the average primary particle size of the pigment is preferably 1 to 200 nm.
• the lower limit is preferably 5 nm or more, and more preferably 10 nm or more.
• the upper limit is preferably 180 nm or less, more preferably 150 nm or less, and even more preferably 100 nm or less.
• the crystallite size of the pigment determined from the half-width of a peak derived from any crystal plane in the X-ray diffraction spectrum when CuK ⁇ radiation is used as the X-ray source, is preferably 0.1 to 100 nm, more preferably 0.5 to 50 nm, even more preferably 1 to 30 nm, and particularly preferably 5 to 25 nm.
• the specific surface area of the pigment is preferably 1 to 300 m 2 /g.
• the lower limit is preferably 10 m 2 /g or more, more preferably 30 m 2 /g or more.
• the upper limit is preferably 250 m 2 /g or less, more preferably 200 m 2 /g or less.
• the value of the specific surface area can be measured according to DIN 66131: determination of the specific surface area of solids by gas adsorption according to the BET (Brunauer, Emmett and Teller) method.
• Red colorants include diketopyrrolopyrrole compounds, anthraquinone compounds, azo compounds, naphthol compounds, azomethine compounds, xanthene compounds, quinacridone compounds, perylene compounds, and thioindigo compounds.
• red colorants include C.I. (Color Index) Pigment Red 1, 2, 3, 4, 5, 6, 7, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 52:1, 52:2, 53:1, 57:1, 60:1, 63:1, 66, 67, 81:1, 81:2, 81:3, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149,
• red pigments include 150, 155, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 200, 202, 206, 207, 208, 209, 210, 216, 220, 224, 226, 242, 246, 254, 255, 264, 269, 270, 272, 279, 291, 294, 295, 296, and 297.
• red colorant a compound described in paragraph 0034 of International Publication No. 2022/085485 and a brominated diketopyrrolopyrrole compound described in JP-A-2020-085947 can also be used.
• Green colorants include phthalocyanine compounds and squarylium compounds, with phthalocyanine compounds being preferred.
• green colorants include green pigments such as C.I. Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65, and 66.
• halogenated zinc phthalocyanine pigments having an average of 10 to 14 halogen atoms, an average of 8 to 12 bromine atoms, and an average of 2 to 5 chlorine atoms in one molecule can also be used as green colorants.
• Specific examples include the compounds described in WO 2015/118720.
• compounds described in paragraph 0029 of WO 2022/085485, aluminum phthalocyanine compounds described in JP 2020-070426 A, and diarylmethane compounds described in JP 2020-504758 A can also be used as green colorants.
• Orange colorants include diketopyrrolopyrrole compounds and azo compounds, and diketopyrrolopyrrole compounds are preferred.
• Specific examples of orange colorants include orange pigments such as C.I. Pigment Orange 2, 5, 13, 16, 17:1, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 71, 73, and 81.
• the orange colorant is preferably at least one selected from C.I. Pigment Orange 71, C.I. Pigment Orange 73, and C.I. Pigment Orange 81.
• Yellow colorants include azo compounds, azomethine compounds, isoindoline compounds, pteridine compounds, quinophthalone compounds, and perylene compounds. Specific examples of yellow colorants include C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125 , 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167,
• an azobarbituric acid nickel complex having the following structure can also be used.
• the compounds described in paragraphs 0031 to 0033 of WO 2022/085485, the methine dyes described in JP 2019-073695 A, and the methine dyes described in JP 2019-073696 A can be used.
• Purple colorants include oxazine compounds, xanthene compounds, pyrromethene compounds, quinacridone compounds, perylene compounds, and thioindigo compounds, with oxazine compounds being preferred.
• Specific examples of purple colorants include purple pigments such as C.I. Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, and 61.
• the blue colorant may be a phthalocyanine compound or a squarylium compound, and is preferably a phthalocyanine compound.
• the blue colorant is preferably a blue pigment.
• Specific examples of the blue colorant include blue pigments such as C.I. Pigment Blue 1, 2, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 22, 29, 60, 64, 66, 79, 80, 87, and 88.
• Aluminum phthalocyanine compounds having phosphorus atoms may also be used as blue colorants. Specific examples include the compounds described in paragraphs 0022 to 0030 of JP-A No. 2012-247591 and paragraph 0047 of JP-A No. 2011-157478.
• Dyes can also be used as other colorants.
• dyes There are no particular limitations on the dyes, and known dyes can be used.
• a dye polymer can also be used as the other colorant.
• the dye polymer is preferably a dye dissolved in a solvent before use.
• the dye polymer may form particles. When the dye polymer is in the form of particles, it is usually used in a state of being dispersed in a solvent.
• the dye polymer in a particle state can be obtained, for example, by emulsion polymerization, and examples of the compound and manufacturing method described in JP-A-2015-214682 include the compound and manufacturing method described therein.
• the dye polymer has two or more dye structures in one molecule, and preferably has three or more dye structures. The upper limit is not particularly limited, but can be 100 or less.
• the multiple dye structures in one molecule may be the same dye structure or different dye structures.
• the weight average molecular weight (Mw) of the dye polymer is preferably 2000 to 50000.
• the lower limit is more preferably 3000 or more, and even more preferably 6000 or more.
• the upper limit is more preferably 30000 or less, and even more preferably 20000 or less.
• the dye multimer may be a compound described in JP2011-213925A, JP2013-041097A, JP2015-028144A, JP2015-030742A, WO2016/031442, etc.
• colorants include triarylmethane dye polymers described in Korean Patent Publication No. 10-2020-0028160, xanthene compounds described in JP 2020-117638 A, phthalocyanine compounds described in WO 2020/174991, isoindoline compounds or salts thereof described in JP 2020-160279 A, compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069442, compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069730, and compounds represented by formula 1 described in Korean Patent Publication No. 10-2020-0069070.
• 10-2020-0069062 halogenated zinc phthalocyanine pigments described in Japanese Patent No. 6809649, isoindoline compounds described in JP-A-2020-180176, phenothiazine compounds described in JP-A-2021-187913, halogenated zinc phthalocyanines described in WO 2022/004261, and halogenated zinc phthalocyanines described in WO 2021/250883 can be used.
• the other colorant may be a rotaxane, and the dye skeleton may be used in the cyclic structure of the rotaxane, may be used in the rod-shaped structure, or may be used in both structures.
• Other colorants include quinophthalone compounds represented by formula 1 in Korean Patent Publication No.
• the colorant contained in the coloring composition may contain two or more chromatic colorants, and may form a black color by combining two or more chromatic colorants.
• a coloring composition is preferably used as a coloring composition for forming an infrared transmission filter.
• Examples of the combination of chromatic colorants when forming a black color by combining two or more chromatic colorants include the following. (1) An embodiment containing a red colorant, a blue colorant, and a yellow colorant. (2) An embodiment containing a red colorant, a blue colorant, a yellow colorant, and a purple colorant. (3) An embodiment containing a red colorant, a blue colorant, a yellow colorant, a purple colorant, and a green colorant. (4) An embodiment containing a red colorant, a blue colorant, a yellow colorant, and a green colorant. (5) An embodiment containing a yellow colorant and a purple colorant.
• a preferred embodiment of the colorant contained in the coloring composition of the present invention is one containing the above-mentioned phthalocyanine mixed crystal pigment and an oxazine compound.
• the shielding properties are excellent in the wavelength range of 600 to 700 nm.
• the oxazine compound is preferably a purple colorant, and more preferably a purple pigment.
• the ratio of the phthalocyanine mixed crystal pigment to the oxazine compound is preferably 5 to 30 parts by mass of the oxazine compound per 100 parts by mass of the phthalocyanine mixed crystal pigment.
• the upper limit is preferably 25 parts by mass or less, and more preferably 20 parts by mass or less.
• the lower limit is preferably 10 parts by mass or more, and more preferably 15 parts by mass or more.
• Another preferred embodiment of the colorant contained in the coloring composition of the present invention includes the above-mentioned phthalocyanine mixed crystal pigment and at least one dye selected from a xanthene dye and a pyrromethene dye.
• This embodiment is excellent in terms of improving the transmittance at a wavelength of 450 nm.
• the xanthene dye and the pyrromethene dye are preferably purple dyes.
• the ratio of the phthalocyanine mixed crystal pigment to the above dye is preferably 5 to 50 parts by mass of the above dye per 100 parts by mass of the specific blue pigment.
• the upper limit is preferably 45 parts by mass or less, and more preferably 40 parts by mass or less.
• the lower limit is preferably 10 parts by mass or more, and more preferably 15 parts by mass or more.
• the content of the colorant in the total solid content of the coloring composition is preferably 20% by mass or more, more preferably 30% by mass or more, even more preferably 40% by mass or more, and particularly preferably 50% by mass or more.
• the upper limit is preferably 80% by mass or less, and more preferably 70% by mass or less.
• the content of the phthalocyanine mixed crystal pigment in the total solid content of the coloring composition is preferably 20% by mass or more, more preferably 30% by mass or more, even more preferably 40% by mass or more, and particularly preferably 50% by mass or more.
• the upper limit is preferably 80% by mass or less, and more preferably 70% by mass or less.
• the content of the phthalocyanine mixed crystal pigment in the colorant is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 65% by mass or more, and particularly preferably 70% by mass or more.
• the phthalocyanine mixed crystal pigment may be used alone or in combination of two or more kinds. When two or more kinds are used in combination, it is preferable that the total amount thereof is within the above range.
• the coloring composition of the present invention contains a resin.
• the resin is blended, for example, for dispersing pigments in the coloring composition or for use as a binder.
• a resin used mainly for dispersing pigments in the coloring composition is also called a dispersant.
• such uses of the resin are merely examples, and the resin can also be used for purposes other than such uses.
• the weight average molecular weight (Mw) of the resin is preferably 3,000 to 2,000,000.
• the upper limit is preferably 1,000,000 or less, and more preferably 500,000 or less.
• the lower limit is preferably 4,000 or more, and more preferably 5,000 or more.
• resins examples include (meth)acrylic resins, epoxy resins, (meth)acrylamide resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, polyarylene ether phosphine oxide resins, polyimide resins, polyamideimide resins, polyolefin resins, cyclic olefin resins, polyester resins, styrene resins, and siloxane resins.
• examples of the resin include the resins described in paragraphs 0091 to 0099 of WO 2022/065215, the blocked polyisocyanate resins described in JP 2016-222891 A, the resins described in JP 2020-122052 A, the resins described in JP 2020-111656 A, the resins described in JP 2020-139021 A, and the resins described in JP 2017-138503 A having a structural unit having a ring structure in the main chain and a biphenyl group in the side chain.
• the resin it is preferable to use a resin having an acid group.
• the acid group include a carboxy group, a phosphate group, a sulfo group, and a phenolic hydroxy group.
• the acid value of the resin having acid groups is preferably 30 to 500 mgKOH/g.
• the lower limit is preferably 40 mgKOH/g or more, and more preferably 50 mgKOH/g or more.
• the upper limit is preferably 400 mgKOH/g or less, more preferably 300 mgKOH/g or less, and even more preferably 200 mgKOH/g or less.
• the weight average molecular weight (Mw) of the resin having acid groups is preferably 5,000 to 100,000, and more preferably 5,000 to 50,000.
• the number average molecular weight (Mn) of the resin having acid groups is preferably 1,000 to 20,000.
• the resin having an acid group preferably contains a repeating unit having an acid group on the side chain, and more preferably contains 5 to 70 mol% of the repeating units having an acid group on the side chain out of all the repeating units of the resin.
• the upper limit of the content of repeating units having an acid group on the side chain is preferably 50 mol% or less, and more preferably 30 mol% or less.
• the lower limit of the content of repeating units having an acid group on the side chain is preferably 10 mol% or more, and more preferably 20 mol% or more.
• the coloring composition of the present invention also 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, more preferably a copolymer having a repeating unit having a basic group in the side chain and a repeating unit not having a basic group, and even more preferably a block copolymer having a repeating unit having a basic group in the side chain and a repeating unit not having a basic group.
• the 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.
• resins with basic groups include DISPERBYK-161, 162, 163, 164, 166, 167, 168, 174, 182, 183, 184, 185, 2000, 2001, 2050, 2150, 2163, 2164, BYK-LPN6919 (all manufactured by BYK-Chemie), Solsperse 11200, 13240, 13650, 13940, 24 000, 26000, 28000, 32000, 32500, 32550, 32600, 33000, 34750, 35100, 35200, 37500, 38500, 39000, 53095, 56000, 7100 (all manufactured by Lubrizol Japan), Efka PX 4300, 4330, 4046, 4060, 4080 (all manufactured by BASF), and the like.
• the resin having a basic group may be a block copolymer (B) described in paragraphs 0063 to 0112 of JP 2014-219665 A, a block copolymer A1 described in paragraphs 0046 to 0076 of JP 2018-156021 A, or a vinyl resin having a basic group described in paragraphs 0150 to 0153 of JP 2019-184763 A, the contents of which are incorporated herein by reference.
• the coloring composition of the present invention also preferably contains both a resin having an acid group and a resin having a basic group. According to this embodiment, the storage stability of the coloring composition can be further improved.
• the content of the resin having a basic group is preferably 20 to 500 parts by mass, more preferably 30 to 300 parts by mass, and even more preferably 50 to 200 parts by mass, per 100 parts by mass of the resin having an acid group.
• a resin having an aromatic carboxy group As the resin, it is also preferable to use a resin having an aromatic carboxy group.
• the aromatic carboxy group may be included in the main chain of a repeating unit, or may be included in a side chain of the repeating unit. It is preferable that the aromatic carboxy group is included in the main chain of a repeating unit.
• an aromatic carboxy group refers to a group having a structure in which one or more carboxy groups are bonded to an aromatic ring.
• the number of carboxy groups bonded to an aromatic ring is preferably 1 to 4, and more preferably 1 to 2.
• resins having an aromatic carboxy group include the resins described in paragraphs 0082 to 0107 of WO 2021/166858.
• the coloring composition of the present invention preferably contains a resin as a dispersant.
• dispersants include acidic dispersants (acidic resins) and basic dispersants (basic resins).
• the term "acidic dispersant (acidic resin)” refers to a resin in which the amount of acid groups is greater than the amount of basic groups.
• the acidic dispersant (acidic resin) is preferably a resin in which the amount of acid groups is 70 mol% or more when the total amount of the acid groups and the basic groups is 100 mol%.
• the acid group possessed by the acidic dispersant (acidic resin) is preferably a carboxy group.
• the acid value of the acidic dispersant (acidic resin) is preferably 10 to 105 mgKOH/g.
• the basic dispersant refers to a resin in which the amount of basic groups is greater than the amount of acid groups.
• the basic dispersant (basic resin) is preferably a resin in which the amount of basic groups is greater than the amount of acid groups when the total amount of the acid groups and the basic groups is 100 mol%.
• the basic group possessed by the basic dispersant is preferably an amino group.
• the resin used as the dispersant is a graft resin.
• graft resins please refer to the description in paragraphs 0025 to 0094 of JP 2012-255128 A, the contents of which are incorporated herein by reference.
• the resin used as the dispersant is a resin having an aromatic carboxy group.
• resins having an aromatic carboxy group include those mentioned above.
• the resin used as the dispersant is preferably a polyimine-based dispersant containing nitrogen atoms in at least one of the main chain and side chain.
• the polyimine-based dispersant is preferably a resin having a main chain with a partial structure having a functional group with a pKa of 14 or less, a side chain with 40 to 10,000 atoms, and having a basic nitrogen atom in at least one of the main chain and side chain.
• the basic nitrogen atom so long as it is a nitrogen atom that exhibits basicity.
• polyimine-based dispersants please refer to the description in paragraphs 0102 to 0166 of JP 2012-255128 A, the contents of which are incorporated herein by reference.
• the resin used as the dispersant is preferably one having a structure in which multiple polymer chains are bonded to a core portion.
• resins include dendrimers (including star-shaped polymers).
• dendrimers include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP 2013-043962 A.
• 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 of the total repeating units of the resin, more preferably 10 to 80 mol %, and even more preferably 20 to 70 mol %.
• resins described in JP 2018-087939 A, block copolymers (EB-1) to (EB-9) described in paragraphs 0219 to 0221 of Japanese Patent No. 6,432,077 A, polyethyleneimine having a polyester side chain described in WO 2016/104803 A, block copolymers described in WO 2019/125940 A, block polymers having an acrylamide structural unit described in JP 2020-066687 A, block polymers having an acrylamide structural unit described in JP 2020-066688 A, dispersants described in WO 2016/104803 A, and the like can also be used.
• Dispersants are also available as commercially available products, and specific examples include the DISPERBYK series manufactured by BYK Chemie, the SOLSPERSE series manufactured by Lubrizol Nippon, the Efka series manufactured by BASF, and the AJISPER series manufactured by Ajinomoto Fine-Techno Co., Ltd.
• the products described in paragraph 0129 of JP2012-137564A and the products described in paragraph 0235 of JP2017-194662A can also be used as dispersants.
• 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, even more 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, and even more preferably 30% by mass or less.
• the content of the resin having an acid group 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, even more 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, and even more preferably 30% by mass or less.
• the content of the dispersant is preferably 10 to 100 parts by mass relative to 100 parts by mass of the pigment.
• the lower limit is preferably 15 parts by mass or more, and more preferably 20 parts by mass or more.
• the upper limit is preferably 80 parts by mass or less, and more preferably 60 parts 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 resins. When two or more types of resins are contained, the total amount thereof is preferably within the above range.
• the coloring composition of the present invention contains a polymerizable compound.
• the polymerizable compound include compounds having an ethylenically unsaturated bond-containing group.
• the ethylenically unsaturated bond-containing group include vinyl groups,
• the polymerizable compound include 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, prepolymer, or oligomer, but is preferably a monomer.
• the molecular weight of the polymerizable compound is preferably 100 to 3,000.
• the upper limit is more preferably 2,000 or less, and even more preferably 1,500 or less.
• the lower limit is more preferably 150 or more, and even more preferably 250 or more.
• the polymerizable compound is preferably a compound containing 3 or more ethylenically unsaturated bond-containing groups, more preferably a compound containing 3 to 15 ethylenically unsaturated bond-containing groups, and even more preferably a compound containing 3 to 6 ethylenically unsaturated bond-containing groups.
• the polymerizable compound is preferably a 3-15 functional (meth)acrylate compound, and more preferably a 3-6 functional (meth)acrylate compound.
• Specific examples of the polymerizable compound include the compounds described in paragraphs 0075 to 0083 of WO 2022/065215 and the compounds described in Taiwan Patent Publication No. 201832008.
• Preferred polymerizable compounds include dipentaerythritol tri(meth)acrylate (commercially available product is KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetra(meth)acrylate (commercially available product is KAYARAD D-320; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol penta(meth)acrylate (commercially available product is KAYARAD D-310; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa(meth)acrylate (commercially available products are KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd., and NK Ester A-DPH-12E; manufactured by Shin-Nakamura Chemical Co., Ltd.), and compounds in which the (meth)acryloyl groups are bonded via ethylene glycol and/or propylene glycol residues (e.g.,
• Examples of the polymerizable compound include diglycerol EO (ethylene oxide) modified (meth)acrylate (commercially available product is M-460; manufactured by Toagosei Co., Ltd.), pentaerythritol tetraacrylate (NK Ester A-TMMT, manufactured by Shin-Nakamura Chemical Co., Ltd.), 1,6-hexanediol diacrylate (KAYARAD HDDA, manufactured by Nippon Kayaku Co., Ltd.), RP-1040 (manufactured by Nippon Kayaku Co., Ltd.), and Aronix TO-2349 (manufactured by Toagosei Co., Ltd.).
• diglycerol EO ethylene oxide
• methacrylate commercially available product is M-460; manufactured by Toagosei Co., Ltd.
• NK Ester A-TMMT pentaerythritol tetraacrylate
• KAYARAD HDDA 1,6-hexanedio
• NK Oligo UA-7200 (Shin-Nakamura Chemical Co., Ltd.), DPHA-40H (Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, T-600, AI-600, LINC-202UA (Kyoeisha Chemical Co., Ltd.), 8UH-1006, 8UH-1012 (all manufactured by Taisei Fine Chemical Co., Ltd.), Light Acrylate POB-A0 (Kyoeisha Chemical Co., Ltd.), etc. can also be used.
• the content of the polymerizable compound in the total solid content of the coloring composition is preferably 1 to 30% by mass.
• the upper limit is preferably 20% by mass or less, more preferably 15% by mass or less, and even more preferably 10% by mass or less.
• the lower limit is preferably 2% by mass or more, and more preferably 5% by mass or more.
• the coloring composition of the present invention may contain only one type of polymerizable compound, or may contain two or more types. When two or more types of polymerizable compounds are contained, it is preferable that the total amount thereof is in the above range.
• the coloring composition of the present invention contains a photopolymerization initiator.
• the photopolymerization initiator is not particularly limited and can be appropriately selected from known photopolymerization initiators. For example, a compound having photosensitivity to light rays in the ultraviolet to visible regions is preferred.
• the photopolymerization initiator is preferably a photoradical polymerization initiator.
• Photopolymerization initiators include halogenated hydrocarbon derivatives (e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.), acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, etc.
• halogenated hydrocarbon derivatives e.g., compounds having a triazine skeleton, compounds having an oxadiazole skeleton, etc.
• acylphosphine compounds e.g., acylphosphine compounds, hexaarylbiimidazole compounds, oxime compounds, organic peroxides, thio compounds, ketone compounds, aromatic onium salts, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, etc.
• the photopolymerization initiator is preferably a trihalomethyltriazine compound, a benzyl dimethyl ketal compound, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, an acylphosphine compound, a phosphine oxide compound, a metallocene compound, an oxime compound, a hexaarylbiimidazole compound, an onium compound, a benzothiazole compound, a benzophenone compound, an acetophenone compound, a cyclopentadiene-benzene-iron complex, a halomethyloxadiazole compound, or a 3-aryl substituted coumarin compound, more preferably a compound selected from an oxime compound, an ⁇ -hydroxyketone compound, an ⁇ -aminoketone compound, and an acylphosphine compound, and even more preferably an oxime compound.
• examples of the photopolymerization initiator include the compounds described in paragraphs 0065 to 0111 of JP 2014-130173 A, the compounds described in Japanese Patent No. 6301489 A, and the compounds described in MATERIAL STAGE 37 to 60p, vol. 19, No.
• hexaarylbiimidazole compounds include 2,2',4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1'-biimidazole.
• ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (all manufactured by IGM Resins B.V.), Irgacure 184, Irgacure 1173, Irgacure 2959, Irgacure 127 (all manufactured by BASF), etc.
• Commercially available ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (all manufactured by IGM Resins B.V.), Irgacure 907, Irgacure 369, Irgacure 369E, Irgacure 379EG (all manufactured by BASF), etc.
• Commercially available acylphosphine compounds include Omnirad 819, Omnirad TPO (all manufactured by IGM Resins B.V.), Irgacure 819, Irgacure TPO (all manufactured by BASF), etc.
• Examples of oxime compounds include the compound described in paragraph 0142 of WO 2022/085485, the compound described in Japanese Patent No. 5,430,746, the compound described in Japanese Patent No. 5,647,738, the compound represented by general formula (1) and the compounds described in paragraphs 0022 to 0024 of JP 2021-173858 A, the compound represented by general formula (1) and the compounds described in paragraphs 0117 to 0120 of JP 2021-170089 A, and the like.
• oxime compound examples include 3-benzoyloxyiminobutan-2-one, 3-acetoxyiminobutan-2-one, 3-propionyloxyiminobutan-2-one, 2-acetoxyiminopentan-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, 2-ethoxycarbonyloxyimino-1-phenylpropan-1-one, 1-[4-(phenylthio)phenyl]-3-cyclohexyl-propane-1,2-dione-2-(O-acetyloxime), and the like.
• an oxime compound having a fluorene ring an oxime compound having a skeleton in which at least one benzene ring of a carbazole ring is a naphthalene ring, an oxime compound having a fluorine atom, an oxime compound having a nitro group, an oxime compound having a benzofuran skeleton, an oxime compound in which a substituent having a hydroxyl group is bonded to a carbazole skeleton, or a compound described in paragraphs 0143 to 0149 of WO 2022/085485 can also be used.
• oxime compounds that are preferably used in the present invention are shown below, but the present invention is not limited to these.
• the oxime compound is preferably a compound having a maximum absorption wavelength in the wavelength range of 350 to 500 nm, more preferably a compound having a maximum absorption wavelength in the wavelength range of 360 to 480 nm.
• the molar absorption coefficient of the oxime compound at a wavelength of 365 nm or 405 nm is preferably high, more preferably 1000 to 300,000, even more preferably 2000 to 300,000, and particularly preferably 5000 to 200,000.
• the molar absorption coefficient of the compound can be measured using a known method. For example, it is preferable to measure using a spectrophotometer (Varian Cary-5 spectrophotometer) at a concentration of 0.01 g/L using ethyl acetate as a solvent.
• 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 good sensitivity can be obtained.
• crystallinity is reduced and solubility in solvents is improved, making it less likely to precipitate over time, and the stability over time of the coloring composition can be improved.
• Specific examples of bifunctional or trifunctional or higher functional photoradical polymerization initiators include the compounds described in paragraph 0148 of WO 2022/065215.
• 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, and even more preferably 10% 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 types are used, it is preferable that the total amount thereof is within the above range.
• the coloring composition of the present invention may contain a pigment derivative.
• the pigment derivative is used, for example, as a dispersing aid for the pigment.
• the dispersing aid is a material for increasing the dispersibility of the pigment in the coloring composition.
• Pigment derivatives include compounds having at least one structure selected from the group consisting of a dye structure and a triazine structure, and an acid group or a basic group.
• the above dye structures include a quinoline dye structure, a benzimidazolone dye structure, a benzisoindole dye structure, a benzothiazole dye structure, an iminium dye structure, a squarylium dye structure, a croconium dye structure, an oxonol dye structure, a pyrrolopyrrole dye structure, a diketopyrrolopyrrole dye structure, an azo dye structure, an azomethine dye structure, a phthalocyanine dye structure, a naphthalocyanine dye structure, an anthraquinone dye structure, a quinacridone dye structure, a dioxazine dye structure, a perinone dye structure, a perylene dye structure, a thiazineindigo dye structure, a thioindigo dye structure, an isoindoline dye structure, an isoindolinone dye structure, a quinophthalone dye structure, a dithiol dye structure
• Examples of the acid group contained in the pigment derivative include a carboxy group, a sulfo group, a phosphate group, a boronic acid group, an imidic acid group, and salts thereof.
• Examples of the atoms or atomic groups constituting the salt include alkali metal ions (Li + , Na + , K +, etc.), alkaline earth metal ions (Ca2 + , Mg2 + , etc.), ammonium ions, imidazolium ions, pyridinium ions, phosphonium ions, etc.
• a group represented by -SO 2 NHSO 2 R X1 , -CONHSO 2 R X2 , -CONHCOR X3 or -SO 2 NHCOR X4 is preferred, a group represented by -SO 2 NHSO 2 R X1 , -CONHSO 2 R X2 or -SO 2 NHCOR X4 is more preferred, and -SO 2 NHSO 2 R X1 or -CONHSO 2 R X2 is even more preferred.
• R X1 to R X4 each independently represent an alkyl group or an aryl group. The alkyl group and aryl group represented by R X1 to R X4 may have a substituent.
• the substituent is preferably a halogen atom, more preferably a fluorine atom.
• R X1 to R X4 each independently represent an alkyl group containing a fluorine atom or an aryl group containing a fluorine atom, more preferably an alkyl group containing a fluorine atom.
• the number of carbon atoms in the alkyl group containing a fluorine atom is preferably 1 to 10, more preferably 1 to 5, and still more preferably 1 to 3.
• the number of carbon atoms in the aryl group containing a fluorine atom is preferably 6 to 20, more preferably 6 to 12, and still more preferably 6.
• Basic groups contained in pigment derivatives include amino groups, pyridinyl groups and their salts, salts of ammonium groups, and phthalimidomethyl groups.
• Atoms or atomic groups that constitute the salts include hydroxide ions, halogen ions, carboxylate ions, sulfonate ions, and phenoxide ions.
• amino group examples include a group represented by --NR.sub.x11R.sub.x12 and a cyclic amino group.
• R x11 and R x12 each independently represent a hydrogen atom, an alkyl group or an aryl group, and are preferably an alkyl group. That is, the amino group is preferably a dialkylamino group.
• the number of carbon atoms of the alkyl group is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3.
• the alkyl group may be linear, branched, or cyclic, but is preferably linear or branched, and more preferably linear.
• the alkyl group may have a substituent. Examples of the substituent include the groups listed in the above-mentioned substituent T.
• the number of carbon atoms of the aryl group is preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 12.
• the aryl group may have a substituent. Examples of the substituent include the groups listed in the above-mentioned substituent T.
• Cyclic amino groups include pyrrolidine groups, piperidine groups, piperazine groups, and morpholine groups. These groups may further have a substituent.
• the pigment derivative may be a pigment derivative having excellent visible transparency (hereinafter, also referred to as a transparent pigment derivative).
• the maximum molar absorption coefficient ( ⁇ max) of the transparent pigment derivative in the wavelength region of 400 to 700 nm is preferably 3000 L mol -1 cm -1 or less, more preferably 1000 L mol -1 cm -1 or less, and even more preferably 100 L mol- 1 cm -1 or less.
• the lower limit of ⁇ max is, for example, 1 L mol -1 cm -1 or more, and may be 10 L mol -1 cm -1 or more.
• pigment derivatives include the compounds described in the Examples below, the compounds described in paragraph 0124 of WO 2022/085485, the benzimidazolone compounds or salts thereof described in JP 2018-168244 A, and the compounds having an isoindoline skeleton described in general formula (1) of Japanese Patent No. 6996282.
• the content of the pigment derivative is preferably 1 to 30 parts by mass, and more preferably 3 to 20 parts by mass, relative to 100 parts by mass of the pigment.
• the total content of the pigment derivative and colorant is preferably 40% by mass or more, more preferably 50% by mass or more, and even more preferably 60% by mass or more, based on the total solid content of the coloring composition.
• the upper limit is preferably 80% by mass or less, and more preferably 70% by mass or less. Only one type of pigment derivative may be used, or two or more types may be used in combination.
• the coloring composition of the present invention may also contain a polyalkyleneimine.
• the polyalkyleneimine is used, for example, as a dispersing aid for pigments.
• the polyalkyleneimine is a polymer obtained by ring-opening polymerization of an alkyleneimine.
• the polyalkyleneimine is preferably a polymer having a branched structure containing a primary amino group, a secondary amino group, and a tertiary amino group.
• the number of carbon atoms in the alkyleneimine is preferably 2 to 6, more preferably 2 to 4, even more preferably 2 or 3, and particularly preferably 2.
• the molecular weight of the polyalkyleneimine is preferably 200 or more, more preferably 250 or more.
• the upper limit is preferably 100,000 or less, more preferably 50,000 or less, even more preferably 10,000 or less, and particularly preferably 2,000 or less.
• the molecular weight of the polyalkyleneimine is the value calculated from the structural formula.
• the molecular weight of the specific amine compound cannot be calculated from the structural formula or is difficult to calculate, the number average molecular weight value measured by the boiling point elevation method is used.
• the number average molecular weight value measured by the viscosity method is used.
• the number average molecular weight value measured in polystyrene equivalent value by GPC (gel permeation chromatography) method is used.
• the amine value of the polyalkyleneimine is preferably 5 mmol/g or more, more preferably 10 mmol/g or more, and even more preferably 15 mmol/g or more.
• alkyleneimines include ethyleneimine, propyleneimine, 1,2-butyleneimine, and 2,3-butyleneimine, with ethyleneimine or propyleneimine being preferred, and ethyleneimine being more preferred.
• the polyalkyleneimine is particularly preferably polyethyleneimine.
• the polyethyleneimine preferably contains primary amino groups in an amount of 10 mol% or more, more preferably 20 mol% or more, and even more preferably 30 mol% or more, based on the total of the primary amino groups, secondary amino groups, and tertiary amino groups.
• Commercially available polyethyleneimines include Epomin SP-003, SP-006, SP-012, SP-018, SP-200, and P-1000 (all manufactured by Nippon Shokubai Co., Ltd.).
• the content of polyalkyleneimine in the total solid content of the coloring composition is preferably 0.1 to 5 mass%.
• the lower limit is preferably 0.2 mass% or more, more preferably 0.5 mass% or more, and even more preferably 1 mass% or more.
• the upper limit is preferably 4.5 mass% or less, more preferably 4 mass% or less, and even more preferably 3 mass% or less.
• the content of polyalkyleneimine is preferably 0.5 to 20 mass parts per 100 mass parts of pigment.
• the lower limit is preferably 0.6 mass% or more, more preferably 1 mass% or more, and even more preferably 2 mass% or more.
• the upper limit is preferably 10 mass% or less, and even more preferably 8 mass% or less. Only one type of polyalkyleneimine may be used, or two or more types may be used. When two or more types are used, the total amount thereof is preferably within the above range.
• the coloring composition of the present invention contains a solvent.
• the solvent include organic solvents.
• the type of solvent is not particularly limited as long as the solubility of each component and the coatability of the composition are satisfied.
• the organic solvent include ester-based solvents, ketone-based solvents, alcohol-based solvents, amide-based solvents, ether-based solvents, and hydrocarbon-based solvents.
• ester-based solvents substituted with a cyclic alkyl group and ketone-based solvents substituted with a cyclic alkyl group can also be preferably used.
• organic solvents include polyethylene glycol monomethyl ether, dichloromethane, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, 2-pentanone, 3-pentanone, 4-heptanone, cyclohexanone, 2-methylcyclohexanone, 3-methylcyclohexanone, 4-methylcyclohexanone, cycloheptanone, cyclooctanone, cyclohexyl acetate, cyclopentanone, ethyl carbitol acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol dimethyl ether, butyl acetate ...
• Examples of the ethylene glycol monomethyl ether acetate include 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N,N-dimethylpropanamide, propylene glycol diacetate, 3-methoxybutanol, methyl ethyl ketone, gamma butyrolactone, sulfolane, anisole, 1,4-diacetoxybutane, diethylene glycol monoethyl ether acetate, butane-1,3-diyl diacetate, dipropylene glycol methyl ether acetate, diacetone alcohol (also known as diacetone alcohol and 4-hydroxy-4-methyl-2-pentanone), 2-methoxypropyl acetate, 2-methoxy-1-propanol, and isopropyl alcohol.
• diacetone alcohol also known as diacetone alcohol and 4-hydroxy-4-methyl-2-pentanone
• 2-methoxypropyl acetate 2-methoxy-1-propanol,
• the amount of aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) used as organic solvents for environmental reasons, etc. (for example, the amount can be 50 ppm (parts per million) by mass or less, 10 ppm by mass or less, or 1 ppm by mass or less, relative to the total amount of organic solvents).
• the metal content of the organic solvent is preferably low.
• the metal content of the organic solvent is preferably, for example, 10 parts per billion (ppb) by mass or less. If necessary, organic solvents at the ppt (parts per trillion) by mass level may be used, and such organic solvents are provided, for example, by Toyo Gosei Co., Ltd. (The Chemical Daily, November 13, 2015).
• Methods for removing impurities such as metals from organic solvents include, for example, distillation (molecular distillation, thin-film distillation, etc.) and filtration using a filter.
• the filter used for filtration preferably has a pore size of 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 with the same number of atoms but different structures).
• the organic solvent may contain only one type of isomer, or multiple types of isomers.
• the peroxide content in the organic solvent is preferably 0.8 mmol/L or less, and more preferably substantially free of peroxide.
• the content of the solvent in the 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 is substantially free of environmentally regulated substances.
• substantially free of environmentally regulated substances means that the content of environmentally regulated substances in the coloring composition is 50 ppm by mass or less, preferably 30 ppm by mass or less, more preferably 10 ppm by mass or less, and particularly preferably 1 ppm by mass or less.
• environmentally regulated substances include benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene.
• distillation methods can be performed at any stage, such as the stage of the raw materials, the stage of the product obtained by reacting the raw materials (for example, a resin solution or a polyfunctional monomer solution after polymerization), or the stage of a colored composition prepared by mixing these compounds.
• the coloring composition of the present invention may further contain an infrared absorbing agent.
• an infrared transmission filter is formed using the coloring composition of the present invention, the wavelength of light transmitted through the film obtained by adding an infrared absorbing agent to the coloring composition can be shifted to a longer wavelength side.
• the infrared absorbing agent is preferably a compound having a maximum absorption wavelength longer than a wavelength of 700 nm.
• the infrared absorbing agent is preferably a compound having a maximum absorption wavelength in the range of more than 700 nm and not more than 1800 nm.
• the ratio A 1 /A 2 between the absorbance A 1 at a wavelength of 500 nm of the infrared absorbing agent and the absorbance A 2 at the maximum absorption wavelength is preferably 0.08 or less, more preferably 0.04 or less.
• Infrared absorbents include pyrrolopyrrole compounds, cyanine compounds, squarylium compounds, phthalocyanine compounds, naphthalocyanine compounds, quaterrylene compounds, merocyanine compounds, croconium compounds, oxonol compounds, iminium compounds, dithiol compounds, triarylmethane compounds, pyrromethene compounds, azomethine compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, metal borides, and the like. Specific examples of these include the compounds described in paragraphs 0114 to 0121 of WO 2022/065215.
• the croconate compound described in JP 2021-195515 A, the infrared absorber described in JP 2022-022070 A, the croconium compound described in WO 2019/021767 A, the compound described in JP 2019-127549 A, the compound described in WO 2022/059619 A, the compound described in JP 2022-151682 A, the squarylium compound described in JP 2022-188858 A, the compound described in JP 2022-184710 A, and the compound described in JP 2022-189736 A can also be used.
• tungsten oxide represented by the following formula described in paragraph 0025 of European Patent No. 3628645 can also be used.
• M 1 and M 2 each represent an ammonium cation or a metal cation, a is 0.01 to 0.5, b is 0 to 0.5, c is 1, d is 2.5 to 3, e is 0.01 to 0.75, n is 1, 2 or 3, m is 1, 2 or 3, and R represents a hydrocarbon group which may have a substituent.
• the content of the infrared absorbing agent 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 even more preferably 10% by mass or more.
• the upper limit is preferably 30% by mass or less, and more preferably 25% by mass or less.
• the coloring composition of the present invention may contain only one type of infrared absorbing agent, or may contain two or more types. When two or more types of infrared absorbing agents are contained, it is preferable that the total amount thereof is within the above range.
• the coloring composition of the present invention may contain a compound having a cyclic ether group.
• the cyclic ether group include an epoxy group and an oxetanyl group.
• the compound having a cyclic ether group is preferably a compound having an epoxy group (hereinafter also referred to as an epoxy compound).
• the epoxy compound include compounds having one or more epoxy groups in one molecule, and compounds having two or more epoxy groups are preferred.
• the epoxy compound is preferably a compound having 1 to 100 epoxy groups in one molecule.
• the upper limit of the epoxy groups contained in the epoxy compound can be, for example, 10 or less, or 5 or less.
• the lower limit of the epoxy groups contained in the epoxy compound is preferably 2 or more.
• Examples of compounds having a cyclic ether group include those described in paragraphs 0034 to 0036 of JP-A-2013-011869, 0147 to 0156 of JP-A-2014-043556, and 0085 to 0092 of JP-A-2014-089408.
• Compounds described in JP-A-2017-179172, xanthene-type epoxy resins described in JP-A-2021-195421, and xanthene-type epoxy resins described in JP-A-2021-195422 can also be used.
• the compound having a cyclic ether group may be a low molecular weight compound (e.g., a molecular weight of less than 2000, or even less than 1000) or a high molecular weight compound (macromolecule) (e.g., a molecular weight of 1000 or more, or in the case of a polymer, a weight average molecular weight of 1000 or more).
• the weight average molecular weight of the compound having an epoxy group is preferably 200 to 100,000, more preferably 500 to 50,000.
• the upper limit of the weight average molecular weight is more preferably 10,000 or less, particularly preferably 5,000 or less, and even more preferably 3,000 or less.
• EHPE3150 manufactured by Daicel Corporation
• EPICLON N-695 manufactured by DIC Corporation
• Marproof G-0150M G-0105SA, G-0130SP, G-0250SP, G-1005S, G-1005SA, G-1010S, G-2050M, G-01100, and G-01758 (all manufactured by NOF Corporation, epoxy group-containing polymers).
• the 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 preferably 0.5% by mass or more, and more preferably 1% by mass or more.
• the upper limit is preferably 15% by mass or less, and more preferably 10% by mass or less. Only one type of compound having a cyclic ether group may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount thereof is within the above range.
• the coloring composition of the present invention may contain a curing accelerator.
• the curing accelerator include a thiol compound, a methylol compound, an amine compound, a phosphonium salt compound, an amidine salt compound, an amide compound, a base generator, an isocyanate compound, an alkoxysilane compound, and an onium salt compound.
• Specific examples of the curing accelerator include the compound described in paragraph 0164 of International Publication No. 2022/085485 and the compound described in JP-A-2021-181406.
• the content of the curing accelerator in the total solid content of the coloring composition is preferably 0.3 to 8.9% by mass, more preferably 0.8 to 6.4% by mass.
• the coloring composition of the present invention may contain an ultraviolet absorber.
• ultraviolet absorbers include conjugated diene compounds, aminodiene compounds, salicylate compounds, benzophenone compounds, benzotriazole compounds, acrylonitrile compounds, hydroxyphenyltriazine compounds, indole compounds, triazine compounds, and dibenzoyl compounds. Specific examples of such compounds include the compounds described in paragraph 0179 of International Publication No. 2022/085485, the reactive triazine ultraviolet absorbers described in JP-A-2021-178918, the ultraviolet absorbers described in JP-A-2022-007884, and the compounds described in Korean Patent Publication No. 10-2022-0014454.
• 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. When two or more types are used, it is preferable that the total amount is within the above range.
• the coloring composition of the present invention may contain a polymerization inhibitor.
• the polymerization inhibitor include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4'-thiobis(3-methyl-6-tert-butylphenol), 2,2'-methylenebis(4-methyl-6-t-butylphenol), and N-nitrosophenylhydroxyamine salts (ammonium salts, cerous salts, etc.).
• p-methoxyphenol is preferred.
• 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 one type or two or more types. In the case of two or more types, the total amount is preferably within the above range.
• the coloring composition of the present invention may contain a silane coupling agent.
• the silane coupling agent include silane compounds having a hydrolyzable group, and it is preferable that the silane coupling agent is a silane compound having a hydrolyzable group and other functional groups.
• the hydrolyzable group refers to a substituent that is directly bonded to a silicon atom and can generate a siloxane bond by at least one of a hydrolysis reaction and a condensation reaction.
• Examples of the hydrolyzable group include a halogen atom, an alkoxy group, and an acyloxy group, and an alkoxy group is preferable.
• the silane coupling agent is preferably a compound having an alkoxysilyl group.
• functional groups other than the hydrolyzable group include a vinyl group, a (meth)allyl group, a (meth)acryloyl group, a mercapto group, an epoxy group, an oxetanyl group, an amino group, a ureido group, a sulfide group, an isocyanate group, and a phenyl group, and an amino group, a (meth)acryloyl group, and an epoxy group are preferable.
• Specific examples of the silane coupling agent include the compounds described in paragraph 0177 of International Publication No.
• the content of the silane coupling agent in the total solid content of the coloring composition is preferably 0.01 to 15.0% by mass, more preferably 0.05 to 10.0% by mass.
• the silane coupling agent may be one type or two or more types. In the case of two or more types, it is preferable that the total amount is within the above range.
• the coloring composition of the present invention may contain a surfactant.
• a surfactant various surfactants such as a fluorine-based surfactant, a nonionic surfactant, a cationic surfactant, an anionic surfactant, and a silicone-based surfactant may be used.
• the surfactant is preferably a silicone-based surfactant or a fluorine-based surfactant, and more preferably a silicone-based surfactant.
• Nonionic surfactants include the compounds described in paragraph 0174 of WO 2022/085485.
• Silicone surfactants include DOWSIL SH8400, SH8400 FLUID, FZ-2122, 67 Additive, 74 Additive, M Additive, SF 8419 OIL (all manufactured by Dow Toray Co., Ltd.), TSF-4300, TSF-4445, TSF-4460, and TSF-4452 (all manufactured by Momentum Co., Ltd.).
• Examples include BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-3760, and BYK-UV3510 (manufactured by BYK-Chemie), etc.
• silicone surfactant may also be a compound having the following structure:
• 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, and more preferably 0.005% by mass to 3.0% by mass.
• the surfactant may be one type or two or more types. When two or more types are used, it is preferable that the total amount is within the above range.
• the coloring composition of the present invention may contain an antioxidant.
• the antioxidant include phenolic compounds, phosphite compounds, and thioether compounds.
• the phenolic compound any phenolic compound known as a phenolic antioxidant may be used.
• a preferred phenolic compound is a hindered phenolic compound.
• a compound having a substituent at the site (ortho position) adjacent to the phenolic hydroxy group is preferred.
• a substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferred.
• a compound having a phenolic group and a phosphite ester group in the same molecule is also preferred.
• a phosphorus-based antioxidant can also be suitably used as the antioxidant.
• phosphorus-based antioxidants include tris[2-[[2,4,8,10-tetrakis(1,1-dimethylethyl)dibenzo[d,f][1,3,2]dioxaphosphepin-6-yl]oxy]ethyl]amine, tris[2-[(4,6,9,11-tetra-tert-butyldibenzo[d,f][1,3,2]dioxaphosphepin-2-yl)oxy]ethyl]amine, and ethylbis(2,4-di-tert-butyl-6-methylphenyl)phosphite.
• antioxidants include, for example, Adeka STAB AO-20, Adeka STAB AO-30, Adeka STAB AO-40, Adeka STAB AO-50, Adeka STAB AO-50F, Adeka STAB AO-60, Adeka STAB AO-60G, Adeka STAB AO-80, and Adeka STAB AO-330 (manufactured by ADEKA Corporation).
• the antioxidant may be a compound described in paragraphs 0023 to 0048 of Japanese Patent No. 6268967, a compound described in International Publication No. WO 2017/006600, a compound described in International Publication No. WO 2017/164024, or a compound described in Korean Patent Publication No. 10-2019-0059371.
• the content of the antioxidant in the total solid content of the coloring composition is preferably 0.01 to 20 mass%, more preferably 0.3 to 15 mass%. Only one type of antioxidant may be used, or two or more types may be used. When two or more types are used, it is preferable that the total amount is in the above range.
• the coloring composition of the present invention may contain, as necessary, a sensitizer, a plasticizer, and other auxiliaries (for example, conductive particles, fillers, defoamers, flame retardants, leveling agents, peeling promoters, fragrances, surface tension regulators, chain transfer agents, etc.).
• auxiliaries for example, conductive particles, fillers, defoamers, flame retardants, leveling agents, peeling promoters, fragrances, surface tension regulators, chain transfer agents, etc.
• the coloring composition of the present invention may contain a metal oxide in order to adjust the refractive index of the resulting film.
• the metal oxide include TiO 2 , ZrO 2 , Al 2 O 3 , and SiO 2 .
• the primary particle size of the metal oxide is preferably 1 to 100 nm, more preferably 3 to 70 nm, and even more preferably 5 to 50 nm.
• the metal oxide may have a core-shell structure. In this case, the core may be hollow.
• the coloring composition of the present invention may contain a light resistance improver.
• the light resistance improver include the compounds described in paragraph 0183 of WO 2022/085485.
• the coloring composition of the present invention is substantially free of terephthalic acid esters.
• substantially free means that the content of terephthalic acid esters in the total amount of the coloring composition is 1000 ppb by mass or less, more preferably 100 ppb by mass or less, and particularly preferably zero.
• the coloring composition of the present invention preferably has a melamine content of 10,000 ppm by mass or less.
• the coloring composition of the present invention preferably has a free metal content of 100 ppm or less, more preferably 50 ppm or less.
• the free halogen content is preferably 100 ppm or less, more preferably 50 ppm or less.
• Methods for reducing free metals and halogens in the coloring composition include washing with ion-exchanged water, filtration, ultrafiltration, and purification with ion-exchange resins.
• perfluoroalkylsulfonic acid and its salts may be restricted.
• the content of perfluoroalkylsulfonic acid (particularly perfluoroalkylsulfonic acid having 6 to 8 carbon atoms in the perfluoroalkyl group) and its salts, and perfluoroalkylcarboxylic acid (particularly perfluoroalkylcarboxylic acid having 6 to 8 carbon atoms in the perfluoroalkyl group) and its salts is preferably in the range of 0.01 ppb to 1,000 ppb, more preferably in the range of 0.05 ppb to 500 ppb, and even more preferably in the range of 0.1 ppb to 300 ppb, based on the total solid content of the coloring composition.
• the coloring composition of the present invention may be substantially free of perfluoroalkylsulfonic acid and its salts, and perfluoroalkylcarboxylic acid and its salts.
• a coloring composition that is substantially free of perfluoroalkylsulfonic acid and its salt, and perfluoroalkylcarboxylic acid and its salt may be selected.
• Examples of compounds that can be a substitute for regulated compounds include compounds that are excluded from the scope of regulation due to the difference in the number of carbon atoms in the perfluoroalkyl group. However, the above content does not prevent the use of perfluoroalkylsulfonic acid and its salt, and perfluoroalkylcarboxylic acid and its salt.
• the coloring composition of the present invention may contain perfluoroalkylsulfonic acid and its salt, and perfluoroalkylcarboxylic acid and its salt within the maximum allowable range.
• the use of fluorine-containing compounds may be restricted.
• the content of fluorine-containing compounds in the coloring composition is preferably 5% by mass or less, more preferably 1% by mass or less, and even more preferably 0.1% by mass or less.
• the coloring composition may be substantially free of fluorine-containing compounds.
• 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 in the range of 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 with its viscosity adjusted for the purpose of adjusting the film surface state (flatness, etc.) and film thickness.
• the viscosity value can be appropriately selected as needed, but for example, it is preferably 0.3 mPa ⁇ s to 50 mPa ⁇ s at 25°C, and more preferably 0.5 mPa ⁇ s to 20 mPa ⁇ s.
• the viscosity can be measured, for example, using a cone-plate type viscometer with the temperature adjusted to 25°C.
• the container for storing the coloring composition is not particularly limited, and a known container can be used.
• the container described in paragraph 0187 of WO 2022/085485 can be used as the container.
• the coloring composition of the present invention can be prepared by mixing the above-mentioned components.
• all the components may be simultaneously dissolved and/or dispersed in a solvent to prepare the coloring composition, or, if necessary, each component may be appropriately prepared as two or more solutions or dispersions, which are mixed at the time of use (at the time of application) to prepare the coloring composition.
• the preparation of the coloring composition includes a process for dispersing the pigment.
• mechanical forces used to disperse the pigment include compression, squeezing, impact, shear, and cavitation.
• Specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high-speed impellers, sand grinders, flow jet mixers, high-pressure wet atomization, and ultrasonic dispersion.
• a sand mill bead mill
• the process and dispersing machine for dispersing the pigment can be suitably used as described in "Dispersion Technology Encyclopedia, published by Joho Kika Co., Ltd., July 15, 2005” or "Dispersion Technology and Industrial Applications Focused on Suspension (Solid/Liquid Dispersion System) - Comprehensive Data Collection, published by Management Development Center Publishing Department, October 10, 1978", and in paragraph 0022 of JP2015-157893A.
• a salt milling process may be performed to refine the particles.
• the descriptions in, for example, JP2015-194521A and JP2012-046629A can be referred to.
• the coloring composition When preparing the coloring composition, it is preferable to filter the coloring composition with a filter for the purpose of removing foreign matter and reducing defects.
• filters and filtration methods used for filtration include the filters and filtration methods described in paragraphs 0196 to 0199 of WO 2022/085485.
• the film of the present invention is obtained from the coloring composition of the present invention described above.
• the film of the present invention can be used for optical filters such as color filters and infrared transmission filters.
• the thickness of the film of the present invention can be adjusted appropriately depending on the purpose.
• the thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and even more preferably 5 ⁇ m or less.
• the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and even more preferably 0.3 ⁇ m or more.
• the film of the present invention When the film of the present invention is used as a color filter, the film of the present invention preferably has a transmittance at a wavelength of 400 nm in the thickness direction of the film of the present invention of 45% or more, more preferably 50% or more, and even more preferably 55% or more.
• the transmittance of the film at a wavelength of 450 nm is preferably 70% or more, more preferably 75% or more, and even more preferably 80% or more.
• the minimum transmittance of the film in the wavelength range of 400 to 500 nm is preferably 40% or more, more preferably 35% or more, and even more preferably 30% or more.
• the maximum transmittance of the film in the wavelength range of 600 to 700 nm is preferably less than 5%, and more preferably less than 3%.
• a film having such spectral characteristics can be preferably used as a blue pixel of a color filter.
• the film of the present invention has, for example, any one of the following spectral characteristics (1) to (4).
• a film having such spectral characteristics can block light in the wavelength range of 400 to 640 nm and transmit light with a wavelength of more than 700 nm.
• a film having such spectral characteristics can block light in the wavelength range of 400 to 750 nm and transmit light with a wavelength of more than 850 nm.
• a film having such spectral characteristics can block light in the wavelength range of 400 to 830 nm and transmit light with a wavelength of more than 940 nm.
• a film having such spectral characteristics can block light in the wavelength range of 400 to 950 nm and transmit light with a wavelength of more than 1040 nm.
• the method for manufacturing a pixel preferably 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 developing and removing the unexposed part of the coloring composition layer 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 (pixel) (post-baking step) may be provided.
• the coloring composition layer is formed on a support using the coloring composition of the present invention.
• the support is not particularly limited and can be appropriately selected depending on the application.
• a glass substrate, a silicon substrate, etc. can be mentioned, and a silicon substrate is preferable.
• a charge-coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, etc. may be formed on the silicon substrate.
• CMOS complementary metal oxide semiconductor
• a black matrix that isolates each pixel may be formed on the silicon substrate.
• a base layer may be provided on the silicon substrate to improve adhesion with the upper layer, prevent diffusion of substances, or flatten the substrate surface.
• the surface contact angle of the base layer is preferably 20 to 70° when measured with diiodomethane. It is also preferable that the surface contact angle is 30 to 80° when measured with water.
• a known method can be used to apply the coloring composition.
• the application method described in paragraph 0207 of WO 2022/085485 can be used.
• the colored composition layer formed on the support may be dried (prebaked).
• prebaking may not be performed.
• the prebaking temperature is preferably 150°C or less, more preferably 120°C or less, and even more preferably 110°C or less.
• the lower limit can be, for example, 50°C or more, and can also be 80°C or more.
• the prebaking time is preferably 10 to 300 seconds, more preferably 40 to 250 seconds, and even more preferably 80 to 220 seconds. Prebaking can be performed using a hot plate, an oven, etc.
• the colored composition layer is exposed to light in a pattern (exposure step).
• the colored composition layer can be exposed to light in a pattern by using a stepper exposure machine or a scanner exposure machine through a mask having a predetermined mask pattern. This allows the exposed parts to be cured.
• Radiation (light) that can be used for exposure includes g-rays and i-rays.
• Light with a wavelength of 300 nm or less (preferably light with a wavelength of 180 to 300 nm) can also be used.
• Examples of light with a wavelength of 300 nm or less include KrF rays (wavelength 248 nm) and ArF rays (wavelength 193 nm), with KrF rays (wavelength 248 nm) being preferred.
• Long-wave light sources of 300 nm or more can also be used.
• As light sources electrodeless ultraviolet lamp systems and hybrid curing of ultraviolet and infrared rays can be used.
• Pulse exposure is an exposure method in which light is applied and paused repeatedly in short cycles (e.g., milliseconds or less).
• the irradiation amount is, for example, preferably 0.03 to 2.5 J/cm 2 , more preferably 0.05 to 1.0 J/cm 2.
• the oxygen concentration during exposure can be appropriately selected, and in addition to being performed under air, for example, exposure may be performed under a low-oxygen atmosphere with an oxygen concentration of 19 volume% or less (e.g., 15 volume%, 5 volume%, or substantially oxygen-free), or exposure may be performed under a high-oxygen atmosphere with an oxygen concentration of more than 21 volume% (e.g., 22 volume%, 30 volume%, or 50 volume%).
• the exposure illuminance can be appropriately set, and can usually be selected from the range of 1000 W/m 2 to 100,000 W/m 2 (e.g., 5,000 W/m 2 , 15,000 W/m 2 , or 35,000 W/m 2 ).
• the oxygen concentration and exposure illuminance may be appropriately combined.
• the oxygen concentration can be 10% by volume and the illuminance can be 10,000 W/m 2
• the oxygen concentration can be 35% by volume and the illuminance can be 20,000 W/m 2 .
• the unexposed parts of the coloring composition layer are developed and removed to form a pattern (pixels).
• the unexposed parts of the coloring composition layer can be developed and removed using a developer.
• the coloring composition layer in the unexposed parts in the exposure step dissolves into the developer, and only the photocured parts remain.
• the temperature of the developer is preferably, for example, 20 to 30°C.
• the development time is preferably 20 to 180 seconds.
• the process of shaking off the developer every 60 seconds and then supplying new developer may be repeated several times.
• the developer may be an organic solvent or an alkaline developer, with an alkaline developer being preferred.
• the developer and the washing (rinsing) method after development may be as described in paragraph 0214 of WO 2022/085485.
• Additional exposure processing and post-baking are curing processing after development to complete curing.
• the heating temperature in post-baking is, for example, preferably 100 to 300°C, more preferably 200 to 270°C.
• Post-baking can be performed continuously or batchwise using a heating means such as a hot plate, a convection oven (hot air circulation dryer), or a high-frequency heater to achieve the above conditions for the developed film.
• a heating means such as a hot plate, a convection oven (hot air circulation dryer), or a high-frequency heater to achieve the above conditions for the developed film.
• the light used for exposure has a wavelength of 400 nm or less.
• additional exposure processing may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
• the optical filter of the present invention has the above-mentioned film of the present invention.
• the types of optical filters include color filters and infrared transmission filters, and the color filter is preferable.
• the color filter preferably has the film of the present invention as a color pixel of the color filter.
• the optical filter may have a protective layer on the surface of the film of the present invention.
• a protective layer By providing a protective layer, various functions such as oxygen blocking, low reflection, hydrophilicity/hydrophobicity, and shielding of light of a specific wavelength (ultraviolet rays, infrared rays, etc.) can be imparted.
• the thickness of the protective layer is preferably 0.01 to 10 ⁇ m, more preferably 0.1 to 5 ⁇ m.
• Methods for forming the protective layer include a method of forming the protective layer by applying a resin composition dissolved in an organic solvent, a chemical vapor deposition method, and a method of attaching a molded resin with an adhesive.
• the components constituting the protective layer include (meth)acrylic resin, ene-thiol resin, polycarbonate resin, polyether resin, polyarylate resin, polysulfone resin, polyethersulfone resin, polyphenylene resin, polyarylene ether phosphine oxide resin, polyimide resin, polyamideimide resin, polyolefin resin, cyclic olefin resin, polyester resin, styrene resin, polyol resin, polyvinylidene chloride resin, melamine resin, urethane resin, aramid resin, polyamide resin, alkyd resin, epoxy resin, modified silicone resin, fluorine resin, polycarbonate resin, polyacrylonitrile resin, cellulose resin, Si, C, W, Al 2 O 3 , Mo, SiO 2 , Si 2 N 4, etc., and may contain two or more of these components.
• the protective layer in the case of a protective layer intended for blocking oxygen, preferably contains a polyol resin, SiO 2 , and Si 2 N 4 .
• the protective layer in the case of a protective layer intended to reduce reflection, preferably contains a (meth)acrylic resin and a fluorine resin.
• a protective layer by applying a resin composition When forming a protective layer by applying a resin composition, known methods such as spin coating, casting, screen printing, and inkjet can be used as a method for applying the resin composition.
• Known organic solvents e.g., propylene glycol 1-monomethyl ether 2-acetate, cyclopentanone, ethyl lactate, etc.
• known chemical vapor deposition methods thermal chemical vapor deposition, plasma chemical vapor deposition, photochemical vapor deposition
• the protective layer may contain additives such as organic or inorganic fine particles, absorbents for light of specific wavelengths (e.g., ultraviolet light, infrared light, etc.), refractive index adjusters, antioxidants, adhesion agents, and surfactants, as necessary.
• organic or inorganic fine particles include polymer fine particles (e.g., silicone resin fine particles, polystyrene fine particles, melamine resin fine particles), titanium oxide, zinc oxide, zirconium oxide, indium oxide, aluminum oxide, titanium nitride, titanium oxynitride, magnesium fluoride, hollow silica, silica, calcium carbonate, and barium sulfate.
• Known absorbents can be used as absorbents for light of specific wavelengths.
• the content of these additives can be adjusted as appropriate, but is preferably 0.1 to 70% by mass, and more preferably 1 to 60% by mass, based on the total mass of the protective layer.
• the protective layer may be the one described in paragraphs 0073 to 0092 of JP2017-151176A.
• the optical filter may have a structure in which each pixel is embedded in a space partitioned by partitions, for example in a grid pattern.
• the solid-state imaging device of the present invention has the above-mentioned film of the present invention.
• the configuration of the solid-state imaging device is not particularly limited as long as it has the film of the present invention and functions as a solid-state imaging device, and examples thereof include the following configurations.
• the substrate has a plurality of photodiodes constituting the light receiving area of a solid-state imaging element (such as a CCD (charge-coupled device) image sensor or a CMOS (complementary metal-oxide semiconductor) image sensor) and a transfer electrode made of polysilicon or the like, a light-shielding film on the photodiodes and the transfer electrode with only the light receiving portion of the photodiode open, a device protection film made of silicon nitride or the like formed on the light-shielding film so as to cover the entire light-shielding film and the light receiving portion of the photodiode, and a color filter on the device protection film.
• a solid-state imaging element such as a CCD (charge-coupled device) image sensor or a CMOS (complementary metal-oxide semiconductor) image sensor
• a transfer electrode made of polysilicon or the like
• the device protection film may have a light-collecting means (e.g., a microlens, etc.; the same applies below) on the device protection film and below the color filter (the side closer to the substrate), or a light-collecting means on the color filter.
• the color filter may have a structure in which each colored pixel is embedded in a space partitioned by partitions, for example in a lattice shape. In this case, it is preferable that the partitions have a lower refractive index than each colored pixel. Examples of imaging devices having such a structure include those described in JP 2012-227478 A, JP 2014-179577 A, and WO 2018/043654 A.
• an ultraviolet absorbing layer may be provided in the structure of the solid-state imaging element to improve light resistance.
• the imaging device equipped with the solid-state imaging element of the present invention can be used for digital cameras, electronic devices with imaging functions (such as mobile phones), as well as in-vehicle cameras and surveillance cameras.
• the image display device of the present invention has the above-mentioned film of the present invention.
• Examples of the image display device include liquid crystal display devices and organic electroluminescence display devices.
• the definition of the image display device and details of each image display device are described, for example, in "Electronic Display Devices” (written by Akio Sasaki, published by Kogyo Chosakai Co., Ltd. in 1990) and “Display Devices” (written by Junsho Ibuki, published by Sangyo Tosho Co., Ltd. in 1989).
• the liquid crystal display device is described, for example, in “Next Generation Liquid Crystal Display Technology” (edited by Tatsuo Uchida, published by Kogyo Chosakai Co., Ltd. in 1994).
• There is no particular limitation on the liquid crystal display device to which the present invention can be applied and the present invention can be applied to various types of liquid crystal display devices described in the above "Next Generation Liquid Crystal Display Technology".
• the obtained wet crystals were washed with water until the washing liquid became neutral, and then air-dried at 50 ° C for 18 hours to obtain 8.7 g of mixed crystal coPc001.
• the mixed crystal oPc001 obtained was subjected to thermogravimetric analysis at a heating rate of 10°C/min under a nitrogen atmosphere using a STA2500 Regulus manufactured by NETZSCH, and as a result, it was confirmed that the thermal decomposition onset temperature was single and different from the temperatures of the raw material phthalocyanines Pc001-Cu and Pc001-Zn, and that it was a mixed crystal.
• the absorption intensity at the wavelength of 400 to 700 nm of the mixed crystal oPc001 was normalized by the absorption intensity at the maximum absorption wavelength in the wavelength range of 550 to 700 nm, the absorption intensity at a wavelength of 400 nm was less than 0.3, and it was a blue pigment.
• the absorption intensity at the maximum absorption wavelength in the wavelength range of 550 to 700 nm was normalized to the absorption intensity in the wavelength range of 400 to 700 nm for each of the mixed crystals coPc002 to coPc013, the absorption intensity at a wavelength of 400 nm was less than 0.3, and they were blue pigments.
• the cooled reaction solution was discharged into a mixed liquid of 10,000 parts by mass of methanol and 2,500 parts by mass of water, and the precipitated solid (polymer) was filtered out, and the filtered solid was washed twice with 500 parts by mass of water.
• the solid after washing was blown and dried at 50°C for 18 hours to obtain a resin B-1 having the following structure.
• the resin B-1 obtained by the above procedure was added to propylene glycol monomethyl ether acetate (hereinafter abbreviated as "PGMEA”) to produce a resin solution (B-1) so that the final resin solution had a resin concentration (solids concentration) of 30%.
• PGMEA propylene glycol monomethyl ether acetate
• glycidyl methacrylate 50.9 parts by mass of glycidyl methacrylate, 0.4 parts by mass of 2,2'-methylenebis(4-methyl-6-t-butylphenol) (hereinafter referred to as "MBMTB”), and 0.8 parts by mass of triethylamine (hereinafter referred to as "TEA”) were charged into the reaction vessel, and the reaction was allowed to proceed at 110°C for 3 hours. After confirming the end of the reaction by measuring the acid value of the reaction solution, 155 parts by mass of DMDG was added to the reaction solution and cooled to room temperature.
• MMTB 2,2'-methylenebis(4-methyl-6-t-butylphenol)
• TAA triethylamine
• Resin B-2 having the following structure:
• the resin B-2 obtained by the above procedure was added to PGMEA to produce a resin solution (B-2) with a resin concentration (solids concentration) of 30% in the final resin solution.
• Resin B-3 having the following structure.
• the resin B-3 obtained by the above procedure was added to PGMEA to produce a resin solution (B-3) with a resin concentration (solids concentration) of 30% in the final resin solution.
• the flask was purged with air, and 35.0 parts by mass of 2-methacryloyloxyethyl isocyanate and 0.1 parts by mass of hydroquinone were charged and reacted at 70°C for 4 hours (third step).
• the reaction solution was cooled to obtain resin B-4 having the following structure.
• either *1 or *2 is bonded to *5 or *6 to form a polyester main chain, and the other is bonded to *3 or *4 to form a polyester main chain.
• Either *3 or *4 is bonded to *1 or *2 to form a polyester main chain, and the other is bonded to an OH group to form a carboxylic acid.
• Either *5 or *6 is bonded to *1 or *2 to form a polyester main chain, and the other is bonded to an OH group to form a carboxylic acid.
• Resin B-4 obtained by the above procedure was added to PGMEA to produce a resin solution (B-4) so that the resin concentration (solid content concentration) of the final resin solution was 30%.
• the obtained kneaded composition was put into 3000 parts by mass of warm water, stirred for 1 hour to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80°C for one day and night to obtain a finely divided pigment (PV23M).
• the average primary particle diameter of the finely divided pigment (PV23M) was 20 to 30 nm.
• the average primary particle diameter of the pigment was determined by determining the projected area of the primary particles of the pigment using a transmission electron microscope, calculating the corresponding circle equivalent diameter as the primary particle diameter, and calculating the arithmetic average value of the primary particle diameters of 400 primary particles of the pigment.
• the amounts of lithium, sodium, potassium and calcium ions contained in the resulting finely divided pigment were measured by inductively coupled plasma optical emission spectroscopy (ICP-OES) using an Optima 7300DV manufactured by PerkinElmer, and each was found to be below the detection limit of 10 ppm.
• ICP-OES inductively coupled plasma optical emission spectroscopy
• XAN-1 Compound having the following structure (xanthene dye, weight average molecular weight 19,000)
• PM-1 Compound having the following structure (pyrromethene dye)
• M-1 ARONIX M-305 (manufactured by Toagosei Co., Ltd., a mixture of pentaerythritol triacrylate and pentaerythritol tetraacrylate. The content of pentaerythritol triacrylate is 55% by mass to 63% by mass.)
• M-2 KAYARAD RP-1040 (manufactured by Nippon Kayaku Co., Ltd., ethylene oxide modified pentaerythritol tetraacrylate)
• M-3 Aronix M-510 (manufactured by Toagosei Co., Ltd., polybasic acid modified acrylic oligomer)
• U-1 Uvinul3050 (manufactured by BASF)
• ⁇ Storage stability evaluation> The viscosity of the colored composition obtained above was measured using "RE-85L” manufactured by Toki Sangyo Co., Ltd., and the colored composition was left to stand at 45°C for 3 days, and then the viscosity was measured again.
• the storage stability was evaluated according to the following evaluation criteria from the viscosity difference ( ⁇ Vis) before and after standing. It can be said that the smaller the viscosity difference ( ⁇ Vis) value, the better the storage stability.
• the viscosity of the colored composition was measured in a state where the temperature was adjusted to 25°C.
• the evaluation criteria were as follows, and the evaluation results are shown in the table below.
• ⁇ Vis is 0.5 mPa ⁇ s or less
• CT-4000L manufactured by FUJIFILM Electronic Materials Co., Ltd.
• CT-4000L manufactured by FUJIFILM Electronic Materials Co., Ltd.
• the wafer was heated at 220° C. for 300 seconds using a hot plate to form an undercoat layer, thereby obtaining a silicon wafer (support) with an undercoat layer.
• each coloring composition was applied by spin coating so that the film thickness after post-baking was 0.6 ⁇ m.
• the wafer was heated at 100° C. for 2 minutes using a hot plate.
• the obtained composition layer was exposed to light (KrF line) with a wavelength of 248 nm through a mask having a 0.5 ⁇ m square pattern using a KrF scanner exposure machine at an illuminance of 35,000 W/m 2 and an exposure dose of 200 mJ/cm 2 .
• the silicon wafer on which the exposed coating film was formed was placed on the horizontal rotating table of a spin-shower developer (DW-30 type, manufactured by Chemitronics Co., Ltd.), and paddle development was performed for 60 seconds at 23°C using a 60% diluted solution of CD-2000 (manufactured by Fujifilm Electronic Materials Co., Ltd.) to form a colored pattern on the silicon wafer.
• the silicon wafer on which the colored pattern was formed was fixed to the horizontal rotating table by a vacuum chuck method, and while rotating the silicon wafer at a rotation speed of 50 rpm by a rotating device, pure water was supplied from a spray nozzle in the form of a shower from above the center of rotation to perform a rinsing treatment, and then spray-dried. Furthermore, a heat treatment (post-bake) was performed for 300 seconds using a hot plate at 200°C to form a colored pattern (pixels). The silicon wafer on which the colored pattern was formed was observed under a scanning electron microscope (SEM) (magnification: 10,000 times), and development residues were evaluated according to the following evaluation criteria.
• SEM scanning electron microscope
• Each colored composition was applied onto a glass substrate by spin coating so that the film thickness after post-baking was 0.6 ⁇ m. Then, the substrate was heated at 100° C. for 2 minutes using a hot plate. Next, the obtained composition layer was exposed to light (KrF line) having a wavelength of 248 nm at an illuminance of 35,000 W/m 2 and an exposure dose of 200 mJ/cm 2 using a KrF scanner exposure machine. Next, a heat treatment (post-baking) was performed for 300 seconds using a hot plate at 200° C. to form a film. The transmittance of the obtained film at wavelengths of 400 to 700 nm was measured using a spectrophotometer (U-4100, manufactured by Hitachi High-Tech Corporation).
• the colored composition of Example 1 was exposed to i-rays at an illuminance of 1000 W/m 2 and an exposure dose of 1000 mJ/cm 2 to evaluate the development residue. The same evaluation results as in the case of exposing the colored composition to KrF rays were obtained.
• the films formed from the colored compositions of the examples can be suitably used in optical filters, solid-state imaging devices, and image display devices.

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