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
  • C09B57/00—Other synthetic dyes of known constitution
  • C09B57/04—Isoindoline dyes
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/006—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
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B5/00—Optical elements other than lenses
  • G02B5/20—Filters
  • G02B5/22—Absorbing filters
• • G—PHYSICS
  • G02—OPTICS
  • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
  • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
  • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
  • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
  • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
  • G02F1/1333—Constructional arrangements; Manufacturing methods
  • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
• • G—PHYSICS
  • G02—OPTICS
  • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
  • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
  • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
  • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
  • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
  • G02F1/1333—Constructional arrangements; Manufacturing methods
  • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
  • G02F1/133509—Filters, e.g. light shielding masks
  • G02F1/133514—Colour filters
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
  • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
  • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
  • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
• • 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
  • H10F39/10—Integrated devices
  • H10F39/12—Image sensors

Definitions

• the present disclosure relates to coloring compositions, films, optical filters, solid-state imaging devices, image display devices, and compounds.
• Optical filters such as color filters are usually manufactured using a coloring composition containing a coloring agent, a photopolymerization initiator, and a polymerizable compound.
• Compositions as described in Patent Documents 1 and 2 are known as conventional coloring compositions.
• Patent Literatures 1 and 2 describe a color filter pigment composition containing an isoindoline compound having a barbituric acid structure.
• the problem to be solved by the embodiments of the present disclosure is to provide a colored composition that gives a colored product with excellent light resistance.
• Another problem to be solved by another embodiment of the present disclosure is to provide a film, an optical filter, a solid-state imaging device, or an image display device using the colored composition.
• a further problem to be solved by other embodiments of the present disclosure is to provide novel compounds.
• Means for solving the above problems include the following aspects. ⁇ 1> A coloring composition containing a compound represented by the following formula 1 and a solvent.
• X represents N or CR 8
• R 1 to R 9 each independently represent a hydrogen atom or a monovalent substituent
• two or more of R 1 to R 9 combine to form a ring
• ⁇ 2> The colored composition according to ⁇ 1>, further comprising a curable compound.
• ⁇ 3> The colored composition according to ⁇ 1> or ⁇ 2>, wherein R 7 or R 8 in formula 1 has an electron-withdrawing group.
• ⁇ 4> The colored composition according to any one of ⁇ 1> to ⁇ 3>, wherein R 1 and R 2 are each independently a hydrogen atom, an alkyl group, or an aryl group.
• ⁇ 5> The colored composition according to ⁇ 4>, wherein R 1 and R 2 are each independently an alkyl group.
• ⁇ 6> The colored composition according to any one of ⁇ 1> to ⁇ 5>, wherein R 9 is a hydrogen atom.
• ⁇ 7> The colored composition according to any one of ⁇ 1> to ⁇ 6>, wherein the compound represented by Formula 1 has a maximum absorption in a wavelength range of 400 nm to 700 nm.
• ⁇ 8> The colored composition according to any one of ⁇ 1> to ⁇ 7>, further comprising a green pigment.
• ⁇ 9> The colored composition according to ⁇ 2>, wherein the curable compound contains a resin.
• ⁇ 11> The colored composition according to any one of ⁇ 1> to ⁇ 10>, which is used for color filters or infrared transmission filters.
• ⁇ 12> The colored composition according to any one of ⁇ 1> to ⁇ 10>, which is for a solid-state imaging device.
• ⁇ 13> A film obtained from the colored composition according to any one of ⁇ 1> to ⁇ 12>.
• ⁇ 14> An optical filter comprising the film according to ⁇ 13>.
• ⁇ 15> A solid-state imaging device comprising the film according to ⁇ 13>.
• ⁇ 16> An image display device comprising the film according to ⁇ 13>.
• ⁇ 17> A compound represented by Formula 1 below.
• X represents N or CR 8
• R 1 to R 9 each independently represent a hydrogen atom or a monovalent substituent
• two or more of R 1 to R 9 combine to form a ring
• a colored composition that gives a colored product with excellent light resistance.
• a film, an optical filter, a solid-state imaging device, or an image display device using the colored composition is provided.
• novel compounds are provided.
• ⁇ is used to include the numerical values before and after it as lower and upper limits.
• a description that does not describe substitution or unsubstituted includes a group (atomic group) having no substituent as well as a group (atomic group) having a substituent.
• an "alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
• exposure includes not only exposure using light but also drawing using particle beams such as electron beams and ion beams, unless otherwise specified.
• Light used for exposure includes actinic rays or radiation such as emission line spectra of mercury lamps, far ultraviolet rays represented by excimer lasers, extreme ultraviolet rays (EUV light), X-rays, and electron beams.
• (meth)acrylate represents both or either acrylate and methacrylate
• (meth)acryl represents both or either acrylic and methacrylic
• (meth) ) acryloyl refers to either or both acryloyl and methacryloyl.
• Me in the structural formulas 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 polystyrene equivalent values measured by GPC (gel permeation chromatography).
• total solid content refers to the total mass of all components of the composition excluding the solvent.
• a pigment means a coloring agent that is difficult to dissolve in a solvent.
• the term "process” includes not only an independent process, but also when the intended action of the process is achieved even if it cannot be clearly distinguished from other processes. . The present disclosure will now be described in detail.
• the coloring composition according to the present disclosure includes a compound represented by Formula 1 below and a solvent.
• X represents N or CR 8
• R 1 to R 9 each independently represent a hydrogen atom or a monovalent substituent
• two or more of R 1 to R 9 combine to form a ring
• C.I. which is an isoindoline pigment
• the present inventors have found that Pigment Yellow 185 has a good spectral waveform and a high color value, but has a problem of low light resistance. As a result of intensive studies by the present inventors, it was found that the use of the above-described configuration yields a colored composition that provides a colored product with excellent light resistance.
• the pyrazolidinedione structure of the compound represented by Formula 1 is C.I.
• Pigment Yellow 185 has a higher stability to light than the barbituric acid structure of Pigment Yellow 185, so it is presumed to have a good spectral waveform, a high color value, and excellent light resistance. As a result, the colored composition according to the present disclosure is presumed to yield a colored product with excellent light resistance.
• the colored composition according to the present disclosure is preferably used as a colored composition for optical filters.
• optical filters include color filters and infrared transmission filters, and color filters are preferred.
• the coloring composition according to the present disclosure is preferably used as a coloring composition for color filters or infrared transmission filters, and 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 a color filter. Pixel types include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, and yellow pixels. Among them, green pixels are preferred.
• the coloring composition according to the present disclosure is preferably used as a coloring composition for solid-state imaging devices.
• the colored composition according to the present disclosure is suitably used as, for example, printing inks, inkjet inks, paints, and the like.
• the maximum transmittance in the wavelength range of 400 nm to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the wavelength range is 1,100 nm to 1,300 nm.
• a filter that satisfies spectral characteristics such that the minimum transmittance is 70% or more (preferably 75% or more, more preferably 80% or more) is preferred.
• the infrared transmission filter is preferably a filter that satisfies any one of the following spectral characteristics (1) to (5).
• the maximum transmittance in the wavelength range of 400 nm to 640 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum transmittance in the wavelength range of 800 nm to 1,500 nm.
• a filter whose value is 70% or more preferably 75% or more, more preferably 80% or more.
• the maximum transmittance in the wavelength range of 400 nm to 750 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the minimum transmittance in the wavelength range of 900 nm to 1,500 nm.
• the maximum transmittance in the wavelength range of 400 nm to 830 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the transmittance in the wavelength range of 1,000 nm to 1,500 nm. is 70% or more (preferably 75% or more, more preferably 80% or more).
• the maximum transmittance in the wavelength range of 400 nm to 950 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and the transmittance in the wavelength range of 1,100 nm to 1,500 nm. is 70% or more (preferably 75% or more, more preferably 80% or more).
• the maximum value of transmittance in the wavelength range of 400 nm to 1,050 nm is 20% or less (preferably 15% or less, more preferably 10% or less), and in the wavelength range of 1,200 nm to 1,500 nm
• the colored composition according to the present disclosure is preferably used for solid-state imaging devices. More specifically, it is preferably used as a coloring composition for optical filters used in solid-state imaging devices, and more preferably used as a coloring composition for color filters used in solid-state imaging devices.
• the solid content concentration of the coloring composition according to the present disclosure is preferably 5% by mass to 30% by mass.
• the lower limit is more preferably 7.5% by mass or more, and even more preferably 10% by mass or more.
• the upper limit is more preferably 25% by mass or less, and even more preferably 20% by mass or less.
• the coloring composition according to the present disclosure includes a compound represented by Formula 1 above. Moreover, the compound represented by Formula 1 is preferably a colorant, and more preferably a yellow pigment.
• R 1 and R 2 in Formula 1 are preferably monovalent substituents from the viewpoint of the light resistance of the resulting colored product (hereinafter also simply referred to as "light resistance") and stability over time, It is more preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably an alkyl group or an aryl group, and an alkyl group having 1 to 20 carbon atoms (also referred to as "the number of carbon atoms") or a carbon number An aryl group having 6 to 20 is even more preferable, and an alkyl group having 1 to 4 carbon atoms, a phenyl group or a benzyl group is particularly preferable.
• the alkyl group and aryl group in R 1 and R 2 may have a substituent.
• the substituent is not particularly limited, preferably a substituent having 0 to 100 carbon atoms, more preferably a substituent having 0 to 50 carbon atoms.
• Examples of the substituents include halogen atoms, hydroxy groups, alkoxy groups, amino groups (unless otherwise specified in the present disclosure, monosubstituted amino groups and disubstituted amino groups are also included.), alkyl groups, and cycloalkyl groups.
• R 1 and R 2 in Formula 1 are each independently preferably an alkyl group, more preferably a methyl group, from the viewpoint of light resistance and stability over time. Furthermore, R 1 and R 2 in formula 1 are preferably the same group from the viewpoint of light resistance and stability over time.
• R 3 and R 6 in Formula 1 are each independently preferably a hydrogen atom, a halogen atom, an alkyl group, or an alkoxy group from the viewpoint of light resistance and stability over time, and preferably a hydrogen atom. More preferred.
• R 4 in Formula 1 is a hydrogen atom, a halogen atom, a hydroxy group, an alkoxy group, an amino group, an alkyl group, a cycloalkyl group, or a heteroaliphatic cyclic group from the viewpoint of light resistance, stability over time, and high color value.
• a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an alkoxy group having 1 to 8 carbon atoms is more preferable, and a hydrogen atom, a t-butyl group, or a methoxy group is particularly preferable.
• R 5 in Formula 1 is a hydrogen atom, a halogen atom, a hydroxy group, an alkoxy group, an amino group, an alkyl group, a cycloalkyl group, or a heteroaliphatic cyclic group from the viewpoint of light resistance, stability over time, and high color value.
• R 4 and R 5 in Formula 1 are preferably bonded to form a ring, and bonded to form an aromatic ring.
• the alkyl group, aryl group, cycloalkyl group, heteroaliphatic cyclic group, amino group, heteroaryl group, acyl group, alkylaminocarbonyl group and alkoxycarbonyl group for R 3 to R 6 in Formula 1 are the substituents described above. may have.
• R 7 in formula 1 is an alkyl group, a cycloalkyl group, a heteroalicyclic group, an aryl group, a heteroaryl group, an acyl group, a nitro group, a cyano A group, an alkylaminocarbonyl group, or an alkoxycarbonyl group, more preferably an electron-withdrawing group, a cyano group, an alkylaminocarbonyl group, or an acyl group, further preferably a cyano A group, a methylaminocarbonyl group, or a 4-chlorobenzoyl group is even more preferred, and a cyano group is particularly preferred.
• X in Formula 1 is preferably CR 8 from the viewpoint of light resistance, stability over time, and high color value.
• R 8 in formula 1 is an alkyl group, cycloalkyl group, heteroalicyclic group, aryl group, heteroaryl group, acyl group, nitro group, cyano group, from the viewpoint of light resistance, stability over time, and high color value.
• X in Formula 1 is CR 8 , it is preferable that R 7 and R 8 combine to form a ring from the viewpoint of light resistance, stability over time, and high color value.
• the compound represented by Formula 1 preferably has one or more electron-withdrawing groups in R 7 or R 8 from the viewpoint of light resistance and stability over time, and both R 7 and R 8 are electrons More preferably, it is an attracting group.
• the alkyl group, cycloalkyl group, heteroaliphatic cyclic group, aryl group, heteroaryl group, acyl group, alkylaminocarbonyl group and alkoxycarbonyl group for R7 and R8 in Formula 1 have the substituents described above.
• R 9 in Formula 1 is preferably a hydrogen atom, an alkyl group, a cycloalkyl group, a heteroalicyclic group, an aryl group, or a heteroaryl group.
• An atom, an alkyl group, or an aryl group is more preferred, and a hydrogen atom is particularly preferred.
• the alkyl group, cycloalkyl group, heteroaliphatic ring group, aryl group and heteroaryl group for R 9 in Formula 1 may have the substituents described above.
• the number of carbon atoms of R 1 to R 9 in Formula 1 is each independently preferably 0 to 50, more preferably 0 to 20, from the viewpoint of light resistance and stability over time. ⁇ 12 is particularly preferred.
• the compound represented by the above formula 1 is preferably a compound represented by the following formula 2 or 3 from the viewpoint of light resistance, stability over time, and high color value, and is represented by the following formula 2 Compounds are more preferred.
• R 1 to R 7 and R 9 to R 13 each independently represent a hydrogen atom or a monovalent substituent, and two or more of R 1 to R 7 and R 9 are bonded to form a ring may form
• R 1 to R 7 and R 9 in formulas 2 and 3 are the same as preferred embodiments of R 1 to R 7 and R 9 in formula 1, respectively.
• Preferred embodiments of R 10 and R 11 in Formula 2 are the same as preferred embodiments of R 7 and R 8 in Formula 1, respectively, except that they are not combined to form a ring.
• Preferred embodiments of R 12 and R 13 in Formula 3 are the same as preferred embodiments of R 1 and R 2 in Formula 1, respectively. From the viewpoint of light resistance, stability over time, and high color value, R 1 and R 13 in formula 3 are preferably the same group, and R 2 and R 12 are the same group. is preferred, and it is more preferred that all of R 1 , R 2 , R 12 and R 13 are the same group.
• the compound represented by the above formula 1 is preferably a compound having a maximum absorption in the wavelength range of 400 nm to 700 nm from the viewpoint of further exerting the effect of the present disclosure, and has a maximum absorption in the wavelength range of 400 nm to 600 nm.
• Compounds are more preferable, and compounds having maximum absorption in the wavelength range of 400 nm to 500 nm are particularly preferable.
• Specific examples of the compound represented by the above formula 1 preferably include compounds (Y-1) to (Y-36) used in Examples described later, but needless to say, the compounds are not limited to these.
• the compound represented by the above formula 1 from the viewpoint of light resistance and high color value, compounds (Y-4) to (Y-9), (Y-14), (Y-15) and At least one compound selected from the group consisting of (Y-24) to (Y-28) is preferred. At least one compound selected from the group consisting of compounds (Y-29) to (Y-36) is also preferred.
• the coloring composition according to the present disclosure may contain one type of compound represented by Formula 1 above, or may contain two or more types. When two or more types are used, the total amount thereof is preferably within the following range.
• the content of the compound represented by the above formula 1 is preferably 1% by mass to 75% by mass based on the total solid content of the coloring composition from the viewpoint of light resistance and stability over time.
• the upper limit is more preferably 70% by mass or less, and even more preferably 65% by mass or less.
• the lower limit is more preferably 2% by mass or more, and even more preferably 5% by mass or more.
• the method for producing the compound represented by Formula 1 is not particularly limited, and the compound may be produced by a known method or by referring to a known method.
• the method for producing the compound represented by the above formula 1 as shown below, at least one of R 7 and R 8 is an electron-withdrawing group, an active methine compound (AM-1) - diiminoisoindoline compound (BM-1) is condensed to synthesize an intermediate (SM-1), and the intermediate (SM-1) is further converted to a pyrazolidinedione compound (CM-1) under acidic conditions. to obtain a compound (TM-1) corresponding to the compound represented by Formula 1.
• the compound (TM-1) may be a tautomer in which R 7 and R 8 are interchanged.
• BM-1 1,3-diiminoisoindoline compound
• CM-1 pyrazolidinedione compound
• raw materials that serve as precursors may be commercially available products, or may be synthesized by known methods.
• the coloring composition according to the present disclosure may contain raw materials and intermediates of the compound represented by Formula 1.
• active methine compound (AM-1) 1,3-diiminoisoindoline compound (BM-1), pyrazolidinedione compound (CM-1), intermediate (SM-1), 1,3-di Reaction products of an iminoisoindoline compound and a pyrazolidinedione compound, salts thereof, and the like.
• BM-1 1,3-diiminoisoindoline compound
• CM-1 pyrazolidinedione compound
• SM-1 1,3-di Reaction products of an iminoisoindoline compound and a pyrazolidinedione compound, salts thereof, and the like.
• the colored composition according to the present disclosure preferably contains a curable compound.
• the curable compound include polymerizable compounds and resins.
• the resin may be a non-polymerizable resin (a resin having no polymerizable group) or a polymerizable resin (a resin having a polymerizable group).
• polymerizable groups include ethylenically unsaturated groups and cyclic ether groups.
• ethylenically unsaturated groups include vinyl groups, (meth)allyl groups, and (meth)acryloyl groups.
• the cyclic ether group include an epoxy group and an oxetanyl group, with the epoxy group being preferred.
• the epoxy group may be a cycloaliphatic epoxy group.
• the alicyclic epoxy group means a monovalent functional group having a cyclic structure in which an epoxy ring and a saturated hydrocarbon ring are condensed.
• the curable compound preferably contains a resin.
• a resin having an acid group and a polymerizable monomer are used as the curable compound.
• the coloring composition according to the present disclosure preferably contains a polymerizable compound.
• the polymerizable compound include compounds having an ethylenically unsaturated group and compounds having a cyclic ether group.
• a compound having an ethylenically unsaturated group can be preferably used as the radically polymerizable compound.
• a compound having a cyclic ether group can also be preferably used as a cationically polymerizable compound.
• resin-type radically polymerizable compounds include resins containing repeating units having radically polymerizable groups.
• the weight average molecular weight (Mw) of the resin type polymerizable compound is preferably 2,000 to 2,000,000.
• the upper limit of the weight average molecular weight is more preferably 1,000,000 or less, and even more preferably 500,000 or less.
• the lower limit of the weight average molecular weight is more preferably 3,000 or more, and even more preferably 5,000 or more.
• the molecular weight of the monomer-type radically polymerizable compound (polymerizable monomer) is preferably less than 2,000, more preferably 1,500 or less.
• the lower limit of the molecular weight of the polymerizable monomer is preferably 100 or more, more preferably 200 or more.
• the compound having an ethylenically unsaturated group as a polymerizable monomer is preferably a 3- to 15-functional (meth)acrylate compound, more preferably a 3- to 6-functional (meth)acrylate compound.
• Specific examples include paragraph numbers 0095 to 0108 of JP-A-2009-288705, paragraph 0227 of JP-A-2013-029760, paragraph numbers 0254-0257 of JP-A-2008-292970, and JP-A-2013-253224.
• Examples of compounds having an ethylenically unsaturated group include dipentaerythritol tri(meth)acrylate (commercially available as KAYARAD D-330; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetra(meth)acrylate (commercially available).
• KAYARAD D-320 is KAYARAD D-320; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol penta(meth)acrylate (commercially available as KAYARAD D-310; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa(meth)acrylate (As a commercial product, KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd., NK Ester A-DPH-12E; manufactured by Shin-Nakamura Chemical Co., Ltd.), and the (meth)acryloyl group of these compounds is ethylene glycol and / or Examples thereof include compounds having a structure linked via a propylene glycol residue (for example, SR454 and SR499 commercially available from Sartomer).
• diglycerin EO ethylene oxide modified (meth) acrylate
• pentaerythritol tetraacrylate Shin-Nakamura Chemical Industry NK Ester A-TMMT, manufactured by Nippon Kayaku Co., Ltd.
• 1,6-hexanediol diacrylate KAYARAD HDDA, manufactured by Nippon Kayaku Co., Ltd.
• RP-1040 manufactured by Nippon Kayaku Co., Ltd.
• Aronix TO-2349 manufactured by Toagosei Co., Ltd.
• NK Oligo UA-7200 manufactured by Shin-Nakamura Chemical Co., Ltd.
• 8UH-1006, 8UH-1012 manufactured by Taisei Fine Chemical Co., Ltd.
• Examples of compounds having an ethylenically unsaturated group include trimethylolpropane tri(meth)acrylate, trimethylolpropane propylene oxide-modified tri(meth)acrylate, trimethylolpropane ethylene oxide-modified tri(meth)acrylate, and isocyanuric acid ethylene oxide-modified tri(meth)acrylate. It is also preferable to use trifunctional (meth)acrylate compounds such as (meth)acrylate and pentaerythritol tri(meth)acrylate. Commercial products of trifunctional (meth)acrylate compounds include Aronix M-309, M-310, M-321, M-350, M-360, M-313, M-315, M-306 and M-305.
• M-303, M-452, M-450 manufactured by Toagosei Co., Ltd.
• a compound having an ethylenically unsaturated group may further have an acid group such as a carboxy group, a sulfo group, or a phosphoric acid group.
• an acid group such as a carboxy group, a sulfo group, or a phosphoric acid group.
• Commercially available products of such compounds include Aronix M-305, M-510, M-520 and Aronix TO-2349 (manufactured by Toagosei Co., Ltd.).
• a compound having a caprolactone structure can also be used as the compound having an ethylenically unsaturated group.
• the description of paragraphs 0042 to 0045 of JP-A-2013-253224 can be referred to, and the contents thereof are incorporated herein.
• Compounds having a caprolactone structure include, for example, DPCA-20, DPCA-30, DPCA-60, DPCA-120, etc., which are commercially available as a series from Nippon Kayaku Co., Ltd.
• a compound having an ethylenically unsaturated group and an alkyleneoxy group can also be used as the compound having an ethylenically unsaturated group.
• Such a compound is preferably a compound having an ethylenically unsaturated group and an ethyleneoxy group and/or a propyleneoxy group, more preferably a compound having an ethylenically unsaturated group and an ethyleneoxy group.
• Tri- to hexa-functional (meth)acrylate compounds having 4 to 20 ethyleneoxy groups are preferred, and more preferred.
• Examples of commercially available products include SR494, a tetrafunctional (meth)acrylate having four ethyleneoxy groups manufactured by Sartomer, and a trifunctional (meth)acrylate having three isobutyleneoxy groups manufactured by Nippon Kayaku Co., Ltd. KAYARAD TPA-330 and the like.
• a polymerizable compound having a fluorene skeleton can also be used as the compound having an ethylenically unsaturated group.
• Commercially available products include Ogsol EA-0200 and EA-0300 (manufactured by Osaka Gas Chemicals Co., Ltd., (meth)acrylate monomer having a fluorene skeleton).
• the compound having an ethylenically unsaturated group it is also preferable to use a compound that does not substantially contain environmental regulation substances such as toluene.
• environmental regulation substances such as toluene.
• Commercially available products of such compounds include KAYARAD DPHA LT and KAYARAD DPEA-12 LT (manufactured by Nippon Kayaku Co., Ltd.).
• Examples of compounds having an ethylenically unsaturated group include UA-7200 (manufactured by Shin-Nakamura Chemical Co., Ltd.), DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.), UA-306H, UA-306T, UA-306I, AH-600, T-600, AI-600, LINC-202UA (manufactured by Kyoeisha Chemical Co., Ltd.), 8UH-1006, 8UH-1012 (manufactured by Taisei Fine Chemical Co., Ltd.), light acrylate POB-A0 (Kyoeisha Chemical Co., Ltd.) Co., Ltd.) is also preferably used.
• Compounds having a cyclic ether group include compounds having an epoxy group, compounds having an oxetanyl group, and the like, and compounds having an epoxy group are preferred.
• Compounds having an epoxy group include compounds having 1 to 100 epoxy groups in one molecule.
• the upper limit of the number of epoxy groups can be, for example, 10 or less, or 5 or less.
• the lower limit of the number of epoxy groups is preferably two or more.
• the compound having a cyclic ether group may be a low-molecular-weight compound (e.g., molecular weight less than 1,000) or a macromolecule (e.g., molecular weight 1,000 or more; in the case of a polymer, a weight-average molecular weight of 1,000). above).
• the weight average molecular weight of the cyclic ether group is preferably from 200 to 100,000, more preferably from 500 to 50,000.
• the upper limit of the weight average molecular weight is preferably 10,000 or less, more preferably 5,000 or less, even more preferably 3000 or less.
• the colored composition according to the present disclosure preferably contains a resin.
• the colored composition according to the present disclosure can use a resin as a curable compound. It is preferable to use a curable compound containing at least a resin.
• the resin is blended, for example, for dispersing a pigment or the like containing the compound represented by Formula 1 in a coloring composition, or for use as a binder.
• a resin mainly used for dispersing a pigment or the like in a coloring composition is also called a dispersant.
• such uses of the resin are only examples, and the resin can be used for purposes other than such uses.
• a resin having a polymerizable group also corresponds to a polymerizable compound.
• the weight average molecular weight of the resin is preferably 3,000 to 2,000,000.
• the upper limit is more preferably 1,000,000 or less, and even more preferably 500,000 or less.
• the lower limit is more preferably 4,000 or more, and even more preferably 5,000 or more.
• resins include (meth)acrylic resins, epoxy resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, polyarylene ether phosphine oxide resins, polyimide resins, Polyamide resins, polyamideimide resins, polyolefin resins, cyclic olefin resins, polyester resins, styrene resins, vinyl acetate resins, polyvinyl alcohol resins, polyvinyl acetal resins, polyurethane resins, polyurea resins, and the like.
• norbornene resin is preferable from the viewpoint of improving heat resistance.
• Commercially available norbornene resins include, for example, the ARTON series manufactured by JSR Corporation (for example, ARTON F4520). Further, as the resin, the resin described in the examples of International Publication No.
• a resin having a fluorene skeleton can also be preferably used.
• the description of US Patent Application Publication No. 2017/0102610 can be referred to, the content of which is incorporated herein.
• the resin the resin described in paragraphs 0199 to 0233 of JP-A-2020-186373, the alkali-soluble resin described in JP-A-2020-186325, and the Korean Patent Publication No. 10-2020-0078339.
• a resin represented by the formula 1 can also be used.
• a resin having an acid group As the resin.
• acid groups include carboxy groups, phosphoric acid groups, sulfo groups, and phenolic hydroxy groups. Only one kind of these acid groups may be used, or two or more kinds thereof may be used.
• a resin having an acid group can be used, for example, as an alkali-soluble resin.
• the acid value of the resin having acid groups is preferably 30 mgKOH/g to 500 mgKOH/g.
• the lower limit is more preferably 50 mgKOH/g or more, still more preferably 70 mgKOH/g or more.
• the upper limit is more preferably 400 mgKOH/g or less, still more preferably 200 mgKOH/g or less, even more preferably 150 mgKOH/g or less, and particularly preferably 120 mgKOH/g or less.
• a resin containing a repeating unit derived from a compound represented by the formula (ED1) and/or a compound represented by the formula (ED2) (hereinafter, these compounds may be referred to as an "ether dimer"). It is also preferred to include
• R 1 and R 2 each independently represent a hydrogen atom or a hydrocarbon group having 1 to 25 carbon atoms which may have a substituent.
• R represents a hydrogen atom or an organic group having 1 to 30 carbon atoms.
• the description in JP-A-2010-168539 can be referred to.
• paragraph number 0317 of JP-A-2013-029760 can be referred to, the contents of which are incorporated herein.
• polymerizable groups include ethylenically unsaturated groups and cyclic ether groups.
• repeating unit Ep at least one type of repeating unit selected from repeating units represented by formula (Ep-1) and repeating units represented by formula (Ep-2).
• a resin hereinafter also referred to as resin Ep
• the resin Ep may contain only one of the repeating units represented by the formula (Ep-1) and the repeating unit represented by the formula (Ep-2). -1) and the repeating unit represented by formula (Ep-2) may be included.
• the ratio of the repeating unit represented by the formula (Ep-1) to the repeating unit represented by the formula (Ep-2) is the molar ratio represented by the formula (Ep-1).
• Repeating unit: repeating unit represented by formula (Ep-2) preferably 5:95 to 95:5, more preferably 10:90 to 90:10, 20:80 to 80 :20 is more preferred.
• L 1 represents a single bond or a divalent linking group
• R 1 represents a hydrogen atom or a substituent.
• the substituent represented by R 1 includes an alkyl group and an aryl group, preferably an alkyl group.
• the number of carbon atoms in the alkyl group is preferably 1-10, more preferably 1-5, and even more preferably 1-3.
• R 1 is preferably a hydrogen atom or a methyl group.
• the divalent linking group represented by L 1 includes an alkylene group (preferably an alkylene group having 1 to 12 carbon atoms), an arylene group (preferably an arylene group having 6 to 20 carbon atoms), -NH-, -SO-, -SO 2 -, -CO-, -O-, -COO-, -OCO-, -S- and a group formed by combining two or more of these.
• the alkylene group may be linear, branched or cyclic, preferably linear or branched.
• the alkylene group may have a substituent or may be unsubstituted. A hydroxy group, an alkoxy group, etc. are mentioned as a substituent.
• the content of the repeating unit Ep in the resin Ep is preferably 1 mol % to 100 mol % of all repeating units in the resin Ep.
• the upper limit is more preferably 90 mol % or less, and even more preferably 80 mol % or less.
• the lower limit is more preferably 2 mol % or more, still more preferably 3 mol % or more.
• the resin Ep may have other repeating units in addition to the repeating unit Ep.
• Other repeating units include a repeating unit having an acid group, a repeating unit having an ethylenically unsaturated group, and the like.
• the acid group includes a phenolic hydroxy group, a carboxy group, a sulfo group, and a phosphoric acid group, preferably a phenolic hydroxy group or a carboxy group, more preferably a carboxy group.
• ethylenically unsaturated groups include vinyl groups, styrene groups, (meth)allyl groups, and (meth)acryloyl groups.
• the content of the repeating unit having an acid group in the resin Ep is preferably 5 mol% to 85 mol% of all repeating units in the resin Ep.
• the upper limit is more preferably 60 mol % or less, even more preferably 40 mol % or less.
• the lower limit is more preferably 8 mol % or more, still more preferably 10 mol % or more.
• the content of the repeating unit having an ethylenically unsaturated group in the resin Ep is 1 mol% to 65 mol% of the total repeating units of the resin Ep. is preferred.
• the upper limit is more preferably 45 mol % or less, even more preferably 30 mol % or less.
• the lower limit is more preferably 2 mol % or more, still more preferably 3 mol % or more.
• the resin Ep preferably further contains a repeating unit having an aromatic hydrocarbon ring.
• the aromatic hydrocarbon ring is preferably a benzene ring or a naphthalene ring, more preferably a benzene ring.
• the aromatic hydrocarbon ring may have a substituent. An alkyl group etc. are mentioned as a substituent.
• the content of the repeating unit having an aromatic hydrocarbon ring is 1 mol% of the total repeating units of the resin having a cyclic ether group. ⁇ 65 mol% is preferred.
• the upper limit is more preferably 45 mol % or less, even more preferably 30 mol % or less.
• the lower limit is more preferably 2 mol % or more, still more preferably 3 mol % or more.
• Repeating units having an aromatic hydrocarbon ring include repeating units derived from monofunctional polymerizable compounds having an aromatic hydrocarbon ring, such as vinyl toluene and benzyl (meth)acrylate.
• the resin it is also preferable to use a resin containing a repeating unit derived from the compound represented by formula (X).
• R 1 represents a hydrogen atom or a methyl group
• R 21 and R 22 each independently represent an alkylene group
• n represents an integer of 0-15.
• the number of carbon atoms in the alkylene group represented by R 21 and R 22 is preferably 1 to 10, more preferably 1 to 5, even more preferably 1 to 3, particularly 2 or 3. preferable.
• n represents an integer of 0 to 15, preferably an integer of 0 to 5, more preferably an integer of 0 to 4, and even more preferably an integer of 0 to 3.
• Examples of the compound represented by formula (X) include ethylene oxide- or propylene oxide-modified (meth)acrylate of paracumylphenol.
• Commercially available products include Aronix M-110 (manufactured by Toagosei Co., Ltd.).
• resin Ac a resin having an aromatic carboxy group
• the aromatic carboxy group may be contained in the main chain of the repeating unit or may be contained in the side chain of the repeating unit.
• the aromatic carboxy group is preferably contained in the main chain of the repeating unit.
• an aromatic carboxy group is a group having a structure in which one or more carboxy groups are bonded to an aromatic ring.
• the number of carboxy groups bonded to the aromatic ring is preferably 1 to 4, more preferably 1 or 2.
• the resin Ac is preferably a resin containing at least one repeating unit selected from repeating units represented by formula (Ac-1) and repeating units represented by formula (Ac-2).
• Ar 1 represents a group containing an aromatic carboxyl group
• L 1 represents -COO- or CONH-
• L 2 represents a divalent linking group
• Ar 10 represents a group containing an aromatic carboxyl group
• L 11 represents -COO- or CONH-
• L 12 represents a trivalent linking group
• P 10 represents a polymer chain.
• Examples of the aromatic carboxy group-containing group represented by Ar 1 in formula (Ac-1) include structures derived from aromatic tricarboxylic acid anhydrides, structures derived from aromatic tetracarboxylic acid anhydrides, and the like.
• Examples of aromatic tricarboxylic anhydrides and aromatic tetracarboxylic anhydrides include compounds having the following structures.
• Q 1 is a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2 -, -C(CF 3 ) 2 -, represented by the following formula (Q-1) or a group represented by the following formula (Q-2).
• the group containing an aromatic carboxyl group represented by Ar 1 may have a polymerizable group.
• the polymerizable group is preferably an ethylenically unsaturated group and a cyclic ether group, more preferably an ethylenically unsaturated group.
• Specific examples of the group containing an aromatic carboxy group represented by Ar 1 include a group represented by formula (Ar-11), a group represented by formula (Ar-12), and a group represented by formula (Ar-13). and the like.
• n1 represents an integer of 1 to 4, preferably 1 or 2, more preferably 2.
• n2 represents an integer of 1 to 8, preferably an integer of 1 to 4, more preferably 1 or 2, and still more preferably 2.
• n3 and n4 each independently represent an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 1 or 2, preferably 1 More preferred. However, at least one of n3 and n4 is an integer of 1 or more.
• Q 1 is a single bond, -O-, -CO-, -COOCH 2 CH 2 OCO-, -SO 2 -, -C(CF 3 ) 2 -, the above formula (Q- 1) or a group represented by the above formula (Q-2).
• *1 represents the bonding position with L1 .
• L 1 represents -COO- or CONH-, preferably -COO-.
• the divalent linking group represented by L 2 in formula (Ac-1) includes an alkylene group, an arylene group, -O-, -CO-, -COO-, -OCO-, -NH-, -S- and these A group obtained by combining two or more of The number of carbon atoms in the alkylene group is preferably 1-30, more preferably 1-20, even more preferably 1-15.
• the alkylene group may be linear, branched or cyclic.
• the arylene group preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and even more preferably 6 to 10 carbon atoms.
• An alkylene group and an arylene group may have a substituent. A hydroxy group etc.
• the divalent linking group represented by L 2 is preferably a group represented by -L 2a -O-.
• L 2a is an alkylene group; an arylene group; a group in which an alkylene group and an arylene group are combined; at least one selected from an alkylene group and an arylene group; Examples include groups in which at least one selected from —NH— and S— are combined, and alkylene groups are preferred.
• the number of carbon atoms in the alkylene group is preferably 1-30, more preferably 1-20, even more preferably 1-15.
• the alkylene group may be linear, branched or cyclic. An alkylene group and an arylene group may have a substituent. A hydroxy group etc. are mentioned as a substituent.
• the group containing an aromatic carboxyl group represented by Ar 10 in formula (Ac-2) has the same meaning as Ar 1 in formula (Ac-1), and preferred embodiments are also the same.
• L 11 represents -COO- or CONH-, preferably -COO-.
• the trivalent linking group represented by L 12 in formula (Ac-2) includes a hydrocarbon group, -O-, -CO-, -COO-, -OCO-, -NH-, -S- and 2 of these Groups in which more than one species are combined are included.
• Hydrocarbon groups include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The number of carbon atoms in the aliphatic hydrocarbon group is preferably 1-30, more preferably 1-20, even more preferably 1-15.
• the aliphatic hydrocarbon group may be linear, branched or cyclic. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6-30, more preferably 6-20, even more preferably 6-10.
• the hydrocarbon group may have a substituent. A hydroxy group etc. are mentioned as a substituent.
• the trivalent linking group represented by L 12 is preferably a group represented by formula (L12-1), more preferably a group represented by formula (L12-2).
• L 12b represents a trivalent linking group
• X 1 represents S
• *1 represents the bonding position with L 11 of formula (Ac-2)
• *2 represents formula ( The binding position of Ac-2) with P10 is shown.
• the trivalent linking group represented by L 12b includes a hydrocarbon group; and at least one selected from -O-, -CO-, -COO-, -OCO-, -NH- and -S- and the like, and a hydrocarbon group or a group of a combination of a hydrocarbon group and —O— is preferred.
• L 12c represents a trivalent linking group
• X 1 represents S
• *1 represents the bonding position with L 11 of formula (Ac-2)
• *2 represents formula ( The binding position of Ac-2) with P10 is shown.
• the trivalent linking group represented by L 12c includes a hydrocarbon group; and at least one selected from -O-, -CO-, -COO-, -OCO-, -NH- and -S- and the like, preferably a hydrocarbon group.
• P 10 in formula (Ac-2) represents a polymer chain.
• the polymer chain represented by P10 preferably has at least one repeating unit selected from poly(meth)acrylic repeating units, polyether repeating units, polyester repeating units and polyol repeating units.
• the weight average molecular weight of the polymer chain P10 is preferably 500-20,000. More preferably, the lower limit is 1,000 or more.
• the upper limit is more preferably 10,000 or less, even more preferably 5,000 or less, and particularly preferably 3,000 or less. If the weight average molecular weight of P10 is within the above range, the dispersibility of the pigment in the composition is good.
• the resin having an aromatic carboxyl group is a resin having repeating units represented by formula (Ac-2), this resin is preferably used as a dispersant.
• the polymer chain represented by P10 may contain a polymerizable group.
• Polymerizable groups include ethylenically unsaturated groups.
• the coloring composition according to the present disclosure preferably contains a resin as a dispersant.
• Dispersants include acidic dispersants (acidic resins) and basic dispersants (basic resins).
• the acidic dispersant (acidic resin) represents a resin in which the amount of acid groups is greater than the amount of basic groups.
• the acidic dispersant (acidic resin) a resin having an acid group content of 70 mol % or more is preferable when the total amount of the acid group and the basic group 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 mgKOH/g to 105 mgKOH/g.
• a basic dispersant represents a resin in which the amount of basic groups is greater than the amount of acid groups.
• a resin containing more than 50 mol % of basic groups is preferable when the total amount of acid groups and 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 also preferably a graft resin.
• graft resin for details of the graft resin, reference can be made to paragraphs 0025 to 0094 of JP-A-2012-255128, the contents of which are incorporated herein.
• the resin used as the dispersant is also preferably a polyimine-based dispersant containing nitrogen atoms in at least one of the main chain and the side chain.
• the polyimine-based dispersant has a main chain having a partial structure having a functional group with a pKa of 14 or less and a side chain having 40 to 10,000 atoms, and at least one of the main chain and the side chain has a basic nitrogen atom.
• a resin having The basic nitrogen atom is not particularly limited as long as it is a nitrogen atom exhibiting basicity.
• the description in paragraphs 0102 to 0166 of JP-A-2012-255128 can be referred to, and the contents thereof are incorporated herein.
• the resin used as the dispersant is also preferably a resin having a structure in which a plurality of polymer chains are bonded to the core.
• resins include, for example, dendrimers (including star polymers).
• dendrimers include polymer compounds C-1 to C-31 described in paragraphs 0196 to 0209 of JP-A-2013-043962.
• the resin used as the dispersant is also preferably a resin containing a repeating unit having an ethylenically unsaturated group in its side chain.
• the content of repeating units having an ethylenically unsaturated group in a side chain is preferably 10 mol% or more, more preferably 10 to 80 mol%, more preferably 20 to 70 mol% of the total repeating units of the resin. is more preferable.
• resins described in JP-A-2018-087939, block copolymers (EB-1) to (EB-9) described in paragraphs 0219 to 0221 of Japanese Patent No. 6432077, Polyethyleneimine having a polyester side chain described in WO 2016/104803, block copolymer described in WO 2019/125940, block polymer having an acrylamide structural unit described in JP 2020-066687 , a block polymer having an acrylamide structural unit described in JP-A-2020-066688, a dispersant described in WO 2016/104803, and the like can also be used.
• the dispersant is also available as a commercial product, and specific examples thereof include the Disperbyk series manufactured by BYK-Chemie (e.g., Disperbyk-111, 161, 2001, etc.), Solsperse manufactured by Nippon Lubrizol Co., Ltd. series (for example, Solsperse 20000, 76500, etc.), Ajinomoto Fine-Techno Co., Inc. Ajisper series, and the like.
• the product described in paragraph number 0129 of JP-A-2012-137564 and the product described in paragraph number 0235 of JP-A-2017-194662 can also be used as a dispersant.
• the content of the curable compound in the total solid content of the coloring composition is preferably 1% by mass to 70% by mass.
• the lower limit is more preferably 2% by mass or more, still more preferably 3% by mass or more, and even more preferably 5% by mass or more.
• the upper limit is more preferably 65% by mass or less, and even more preferably 60% by mass or less.
• the coloring composition according to the present disclosure may contain only one type of curable compound, or may contain two or more types. When two or more curable compounds are included, the total amount thereof is preferably within the above range.
• the content of the polymerizable compound is preferably 1% by mass to 70% by mass with respect to the total solid content of the coloring composition.
• the lower limit is more preferably 2% by mass or more, still more preferably 3% by mass or more, and even more preferably 5% by mass or more.
• the upper limit is more preferably 65% by mass or less, and even more preferably 60% by mass or less.
• the coloring composition according to the present disclosure may contain only one polymerizable compound, or may contain two or more polymerizable compounds. When two or more polymerizable compounds are included, the total amount thereof is preferably within the above range.
• the content of the polymerizable monomer is preferably 1% by mass to 50% by mass with respect to the total solid content of the coloring composition.
• the lower limit is more preferably 2% by mass or more, still more preferably 3% by mass or more, and even more preferably 5% by mass or more.
• the upper limit is more preferably 35% by mass or less, even more preferably 30% by mass or less, and even more preferably 20% by mass or less.
• the coloring composition according to the present disclosure may contain only one polymerizable monomer, or may contain two or more polymerizable monomers. When two or more polymerizable monomers are included, the total amount thereof is preferably within the above range.
• the content of the resin is preferably 1% to 70% by weight with respect to the total solid content of the coloring composition.
• the lower limit is more preferably 2% by mass or more, still more preferably 3% by mass or more, and even more preferably 5% by mass or more.
• the upper limit is more preferably 65% by mass or less, and even more preferably 60% by mass or less.
• the content of the resin having an acid group is preferably 1% by mass to 70% by mass with respect to the total solid content of the coloring composition.
• the lower limit is more preferably 2% by mass or more, still more preferably 3% by mass or more, and even more preferably 5% by mass or more.
• the upper limit is more preferably 65% by mass or less, and even more preferably 60% by mass or less.
• the content of the alkali-soluble resin is preferably 1% by mass to 70% by mass with respect to the total solid content of the coloring composition.
• the lower limit is more preferably 2% by mass or more, still more preferably 3% by mass or more, and even more preferably 5% by mass or more.
• the upper limit is more preferably 65% by mass or less, and even more preferably 60% by mass or less.
• the coloring composition according to the present disclosure contains a resin as a dispersant
• the content of the resin as a dispersant is preferably 0.1% by mass to 30% by mass with respect to the total solid content of the coloring composition.
• the upper limit is more preferably 25% by mass or less, and even more preferably 20% by mass or less.
• the lower limit is more preferably 0.5% by mass or more, and even more preferably 1% by mass or more.
• the content of the resin as a dispersant is preferably 1% by mass to 100% by mass with respect to 100% by mass of the pigment containing the compound represented by formula (1).
• the upper limit is more preferably 80 parts by mass or less, even more preferably 70 parts by mass or less, and even more preferably 60 parts by mass or less.
• the lower limit is more preferably 5 parts by mass or more, still more preferably 10 parts by mass or more, and even more preferably 20 parts by mass or more.
• the coloring composition according to the present disclosure may contain only one resin, or may contain two or more resins. When two or more resins are included, the total amount thereof is preferably within the above range.
• a colored composition according to the present disclosure may comprise a photoinitiator.
• the colored composition according to the present disclosure preferably contains a photopolymerization initiator.
• the photopolymerization initiator is not particularly limited and can be appropriately selected from known photopolymerization initiators. For example, compounds having photosensitivity to light in the ultraviolet range to the visible range are 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 and the like.
• 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 and the like.
• photopolymerization initiators include trihalomethyltriazine compounds, benzyldimethylketal compounds, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, acylphosphine compounds, phosphine oxide compounds, metallocene compounds, oxime compounds, hexaarylbi At least one compound selected from the group consisting of imidazole compounds, onium compounds, benzothiazole compounds, benzophenone compounds, acetophenone compounds, cyclopentadiene-benzene-iron complexes, halomethyloxadiazole compounds and 3-aryl-substituted coumarin compounds.
• oxime compounds More preferably, it is at least one compound selected from the group consisting of oxime compounds, ⁇ -hydroxyketone compounds, ⁇ -aminoketone compounds, and acylphosphine compounds, and even more preferably oxime compounds.
• the photopolymerization initiator compounds described in paragraphs 0065 to 0111 of JP-A-2014-130173, compounds described in Japanese Patent No. 6301489, MATERIAL STAGE 37-60p, vol. 19, No. 3, the peroxide photopolymerization initiator described in 2019, the photopolymerization initiator described in International Publication No. 2018/221177, the photopolymerization initiator described in International Publication No.
• hexaarylbiimidazole compounds include 2,2′,4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1′-biimidazole, etc. are mentioned.
• ⁇ -hydroxyketone compounds include Omnirad 184, Omnirad 1173, Omnirad 2959, Omnirad 127 (manufactured by IGM Resins B.V.), Irgacure 184, Irgacure 1173, Irgacure 2959, Irgacure 1173, Irgacure 127 ( company) and the like.
• ⁇ -aminoketone compounds include Omnirad 907, Omnirad 369, Omnirad 369E, Omnirad 379EG (manufactured by IGM Resins B.V.), Irgacure 907, Irgacure 369, Irgacure 369E, Irgacure 379EG (manufactured by Irgacure 369E, Irgacure 379EG). made), etc.
• acylphosphine compounds include Omnirad 819, Omnirad TPO (manufactured by IGM Resins B.V.), Irgacure 819, and Irgacure TPO (manufactured by BASF).
• Examples of the oxime compound include compounds described in JP-A-2001-233842, compounds described in JP-A-2000-080068, compounds described in JP-A-2006-342166, J. Am. C. S. compounds described in Perkin II (1979, pp. 1653-1660); C. S. Perkin II (1979, pp.156-162), compounds described in Journal of Photopolymer Science and Technology (1995, pp.202-232), compounds described in JP-A-2000-066385, Compounds described in JP-A-2004-534797, compounds described in JP-A-2017-019766, compounds described in Patent No.
• oxime compounds include 3-benzoyloxyiminobutane-2-one, 3-acetoxyiminobutane-2-one, 3-propionyloxyiminobutane-2-one, 2-acetoxyiminopentane-3-one, 2-acetoxyimino-1-phenylpropan-1-one, 2-benzoyloxyimino-1-phenylpropan-1-one, 3-(4-toluenesulfonyloxy)iminobutan-2-one, 2-ethoxycarbonyloxyimino -1-phenylpropane-1-one, 1-[4-(phenylthio)phenyl]-3-cyclohexyl-propane-1,2-dione-2-(O-acetyloxime) and the like.
• Photopolymerization initiator 2 described in JP-A-2012-014052 manufactured by ADEKA.
• the oxime compound it is also preferable to use a compound having no coloring property or a compound having high transparency and resistance to discoloration.
• An oxime compound having a fluorene ring can also be used as the oxime compound.
• Specific examples of the oxime compound having a fluorene ring include compounds described in JP-A-2014-137466, compounds described in Japanese Patent No. 6636081, and compounds described in Korean Patent Publication No. 10-2016-0109444. mentioned.
• an oxime compound having a skeleton in which at least one benzene ring of the carbazole ring is a naphthalene ring can also be used.
• Specific examples of such oxime compounds include compounds described in WO2013/083505.
• An oxime compound having a fluorine atom can also be used as the oxime compound.
• Specific examples of the oxime compound having a fluorine atom include compounds described in JP-A-2010-262028, compounds 24, 36 to 40 described in JP-A-2014-500852, and JP-A-2013-164471. and the compound (C-3) of.
• an oxime compound having a nitro group can be used as the oxime compound.
• the oxime compound having a nitro group is also preferably a dimer.
• Specific examples of the oxime compound having a nitro group include compounds described in paragraph numbers 0031 to 0047 of JP-A-2013-114249 and paragraph numbers 0008-0012 and 0070-0079 of JP-A-2014-137466; Compounds described in paragraphs 0007 to 0025 of Japanese Patent No. 4223071 and ADEKA Arkles NCI-831 (manufactured by ADEKA Corporation) can be mentioned.
• An oxime compound having a benzofuran skeleton can also be used as the oxime compound.
• Specific examples include OE-01 to OE-75 described in WO 2015/036910.
• an oxime compound in which a substituent having a hydroxy group is bonded to the carbazole skeleton can also be used.
• Examples of such a photopolymerization initiator include the compounds described in International Publication No. 2019/088055.
• an oxime compound having an aromatic ring group Ar 2 OX1 in which an electron-withdrawing group is introduced into the aromatic ring (hereinafter also referred to as oxime compound OX) can be used.
• the electron-withdrawing group possessed by the aromatic ring group Ar OX1 include an acyl group, a nitro group, a trifluoromethyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, and a cyano group.
• a benzoyl group may have a substituent.
• substituents include halogen atoms, cyano groups, nitro groups, hydroxy groups, alkyl groups, alkoxy groups, aryl groups, aryloxy groups, heterocyclic groups, heterocyclic oxy groups, alkenyl groups, alkylsulfanyl groups, arylsulfanyl groups, It is preferably an acyl group or an amino group, more preferably an alkyl group, an alkoxy group, an aryl group, an aryloxy group, a heterocyclic oxy group, an alkylsulfanyl group, an arylsulfanyl group or an amino group.
• a sulfanyl group or an amino group is more preferred.
• the oxime compound OX is preferably at least one selected from the compounds represented by the formula (OX1) and the compounds represented by the formula (OX2), more preferably the compound represented by the formula (OX2). preferable.
• R X1 is an alkyl group, alkenyl group, alkoxy group, aryl group, aryloxy group, heterocyclic group, heterocyclicoxy group, alkylsulfanyl group, arylsulfanyl group, alkylsulfinyl group, arylsulfinyl group, alkylsulfonyl a group, an arylsulfonyl group, an acyl group, an acyloxy group, an amino group, a phosphinoyl group, a carbamoyl group or a sulfamoyl group
• R X2 is an alkyl group, alkenyl group, alkoxy group, aryl group, aryloxy group, heterocyclic group, heterocyclicoxy group, alkylsulfanyl group, arylsulfanyl group, alkylsulfinyl group, arylsulfinyl group, alkylsulf
• the electron-withdrawing group includes an acyl group, a nitro group, a trifluoromethyl group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, and a cyano group, preferably an acyl group or a nitro group.
• An acyl group is more preferred, and a benzoyl group is even more preferred, because a film having excellent properties can be easily formed.
• R X12 is an electron-withdrawing group
• R X10 , R X11 , R X13 and R X14 are preferably hydrogen atoms.
• oxime compound OX examples include compounds described in paragraphs 0083 to 0105 of Japanese Patent No. 4600600.
• oxime compounds preferably used in the present disclosure are shown below, but are not limited to these.
• the oxime compound is preferably a compound having a maximum absorption wavelength in the wavelength range of 350 nm to 500 nm, more preferably a compound having a maximum absorption wavelength in the wavelength range of 360 nm to 480 nm.
• the molar extinction coefficient of the oxime compound at a wavelength of 365 nm or a wavelength of 405 nm is preferably high from the viewpoint of sensitivity, preferably 1,000 to 300,000, and more preferably 2,000 to 300,000. More preferably, it is particularly preferably from 5,000 to 200,000.
• the molar extinction coefficient of a compound can be measured using known methods. For example, it is preferable to measure with a spectrophotometer (Cary-5 spectrophotometer manufactured by Varian) using an ethyl acetate solvent at a concentration of 0.01 g/L.
• Irgacure OXE01 manufactured by BASF
• Irgacure OXE02 manufactured by BASF
• Omnirad 2959 manufactured by IGM Resins B.V.
• a bifunctional or trifunctional or higher functional radical photopolymerization initiator may be used as the photopolymerization initiator.
• a radical photopolymerization initiator two or more radicals are generated from one molecule of the radical photopolymerization initiator, so good sensitivity can be obtained.
• the crystallinity is reduced, the solubility in a solvent or the like is improved, and precipitation becomes difficult over time, and the stability over time of the colored composition can be improved.
• bifunctional or trifunctional or higher photoradical polymerization initiators include those described in JP-T-2010-527339, JP-T-2011-524436, WO-2015/004565, JP-T-2016-532675.
• the content of the photopolymerization initiator in the total solid content of the coloring composition is preferably 0.1% by mass to 20% by mass.
• the lower limit is more preferably 0.5% by mass or more, and particularly preferably 1% by mass or more.
• the upper limit is more preferably 15% by mass or less, particularly 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 kinds are used, it is preferable that the total amount thereof is within the above range.
• the coloring composition according to the present disclosure may contain other coloring agents than the compound represented by Formula 1.
• Other colorants include chromatic colorants and black colorants.
• chromatic coloring agents include coloring agents having a maximum absorption wavelength in the wavelength range of 400 nm to 700 nm. Examples include green colorants, red colorants, yellow colorants, purple colorants, blue colorants, orange colorants, and the like.
• the other coloring agent is preferably a chromatic coloring agent, more preferably a green coloring agent, and particularly preferably a green pigment.
• Other coloring agents may be pigments or dyes, but are preferably pigments.
• the average primary particle size of the pigment is preferably 1 nm to 200 nm.
• the lower limit is more preferably 5 nm or more, and even more preferably 10 nm or more.
• the upper limit is more preferably 180 nm or less, still more preferably 150 nm or less, and particularly preferably 100 nm or less.
• the primary particle diameter of the pigment can be determined from the image photograph obtained by observing the primary particles of the pigment with a transmission electron microscope. Specifically, the projected area of the primary particles of the pigment is obtained, and the corresponding circle equivalent diameter is calculated as the primary particle diameter of the pigment.
• the average primary particle size in this specification is the arithmetic mean value of the primary particle sizes of 400 primary particles of the pigment.
• the primary particles of the pigment refer to independent particles without agglomeration.
• green colorants examples include phthalocyanine compounds and squarylium compounds, with phthalocyanine compounds being preferred.
• the green colorant is preferably a pigment.
• Specific examples of green colorants include C.I. I. Green pigments such as Pigment Green 7, 10, 36, 37, 58, 59, 62, 63, 64, 65 and 66 are included.
• a green colorant a halogenated zinc phthalocyanine having an average number of halogen atoms of 10 to 14, an average number of bromine atoms of 8 to 12, and an average number of chlorine atoms of 2 to 5 per molecule. Pigments can also be used. Specific examples include compounds described in International Publication No. 2015/118720.
• the compound described in Chinese Patent Application No. 106909027 the phthalocyanine compound having a phosphoric acid ester as a ligand described in WO 2012/102395, described in JP 2019-008014.
• the phthalocyanine compound, the phthalocyanine compound described in JP-A-2018-180023, the compound described in JP-A-2019-038958, the aluminum phthalocyanine compound described in JP-A-2020-070426, JP-A-2020-076995 Core-shell type dyes described in, diarylmethane compounds described in JP-A-2020-504758, and the like can also be used.
• the green colorant is C.I. I. Pigment Green 7, 36, 58, 59, 62 and 63 are preferred, C.I. I. Pigment Green 7, 36, 58 and 59 are more preferred.
• red colorants examples include diketopyrrolopyrrole compounds, anthraquinone compounds, azo compounds, naphthol compounds, azomethine compounds, xanthene compounds, quinacridone compounds, perylene compounds, thioindigo compounds, and diketopyrrolopyrrole compounds, anthraquinone compounds, azo It is preferably a compound, more preferably a diketopyrrolopyrrole compound. Also, the red colorant is preferably a pigment. Specific examples of red colorants include C.I. I.
• a red colorant a diketopyrrolopyrrole compound in which at least one bromine atom is substituted in the structure described in JP-A-2017-201384, a diketopyrrolopyrrole described in paragraphs 0016 to 0022 of Japanese Patent No.
• 10-2019-0140741 anthraquinone compounds described in Korean Patent Publication No. 10-2019-0140744, JP 2020 -Perylene compounds described in JP-A-079396, perylene compounds described in JP-A-2020-083982, xanthene compounds described in JP-A-2018-035345, paragraph numbers 0025 to 0041 of JP-A-2020-066702
• the described diketopyrrolopyrrole compounds and the like can also be used.
• red colorant a compound having a structure in which an aromatic ring group in which a group having an oxygen atom, a sulfur atom or a nitrogen atom is bonded to an aromatic ring is bonded to a diketopyrrolopyrrole skeleton is used.
• Lumogen F Orange 240 manufactured by BASF, red pigment, perylene pigment
• red colorant can also be used as a red colorant.
• the red coloring agent is C.I. I. Pigment Red 122, 177, 179, 254, 255, 264, 269, 272 and 291 are preferred, and C.I. I. Pigment Red 254, 264, 272 are more preferred.
• yellow colorants examples include azo compounds, azomethine compounds, isoindoline compounds, pteridine compounds, quinophthalone compounds and perylene compounds.
• the yellow colorant is preferably a pigment, more preferably an azo pigment, an azomethine pigment, an isoindoline pigment, a pteridine pigment, a quinophthalone pigment or a perylene pigment, more preferably an azo pigment or an azomethine pigment.
• Specific examples of yellow colorants include C.I. I.
• a nickel azobarbiturate complex having the following structure can also be used as a yellow colorant.
• X 1 to X 16 each independently represent a hydrogen atom or a halogen atom
• Z 1 represents an alkylene group having 1 to 3 carbon atoms.
• Specific examples of the compound represented by formula (QP1) include compounds described in paragraph 0016 of Japanese Patent No. 6443711.
• Y 1 to Y 3 each independently represent a halogen atom.
• n and m are integers from 0 to 6; p is an integer from 0 to 5; (n+m) is 1 or more.
• Specific examples of the compound represented by formula (QP2) include compounds described in paragraphs 0047 to 0048 of Japanese Patent No. 6432077.
• the yellow coloring agent is C.I. I. Pigment Yellow 117, 129, 138, 139, 150 and 185 are preferred.
• C.I. I. Pigment Orange 2 5, 13, 16, 17: 1, 31, 34, 36, 38, 43, 46, 48, 49, 51, 52, 55, 59, 60, 61, 62, 64, 71, 73, etc. of orange pigments.
• C.I. I. Purple pigments such as Pigment Violet 1, 19, 23, 27, 32, 37, 42, 60, and 61 are included.
• C.I. I. pigment blue 1, 2, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 29, 60, 64, 66, 79, 80, 87, 88, etc. be done.
• An aluminum phthalocyanine compound having a phosphorus atom can also be used as a blue colorant. Specific examples include compounds described in paragraph numbers 0022 to 0030 of JP-A-2012-247591 and paragraph number 0047 of JP-A-2011-157478.
• Dyes can also be used as chromatic colorants.
• the dye is not particularly limited, and known dyes can be used.
• a pigment multimer can also be used as a chromatic colorant.
• the dye multimer is preferably a dye dissolved in an organic solvent. Further, the dye multimer may form particles. When the dye multimer is particles, it is usually used in a state of being dispersed in a solvent.
• the particulate dye multimer can be obtained, for example, by emulsion polymerization, and specific examples include the compounds and production methods described in JP-A-2015-214682.
• a dye multimer has two or more dye structures in one molecule, and preferably has three or more dye structures. The upper limit is not particularly limited, but may be 100 or less.
• a plurality of dye structures in one molecule may be the same dye structure or different dye structures.
• the weight average molecular weight (Mw) of the dye multimer is preferably 2,000 to 50,000.
• the lower limit is more preferably 3000 or more, and even more preferably 6000 or more.
• the upper limit is more preferably 30,000 or less, and even more preferably 20,000 or less.
• Dye multimers are described in JP-A-2011-213925, JP-A-2013-041097, JP-A-2015-028144, JP-A-2015-030742, WO 2016/031442, etc. Compounds can also be used.
• the chromatic colorants include diarylmethane compounds described in JP-A-2020-504758, triarylmethane dye polymers described in Korean Patent Publication No. 10-2020-0028160, and JP-A-2020-117638.
• Xanthene compounds described phthalocyanine compounds described in International Publication No. 2020/174991, isoindoline compounds described in JP-A-2020-160279 or salts thereof, Korean Patent Publication No. 10-2020-0069442 described in Compound represented by formula 1, compound represented by formula 1 described in Korean Patent Publication No. 10-2020-0069730, represented by formula 1 described in Korean Patent Publication No. 10-2020-0069070
• the chromatic 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-like structure, or may be used in both structures.
• Two or more chromatic colorants may be used in combination.
• black may be formed by a combination of two or more chromatic colorants.
• the black colorant is not particularly limited, and known ones can be used.
• inorganic black colorants include carbon black, titanium black, graphite, etc.
• Carbon black or titanium black is preferred, and titanium black is more preferred.
• Titanium black is black particles containing titanium atoms, preferably low order titanium oxide or titanium oxynitride. Titanium black can be surface-modified as necessary for the purpose of improving dispersibility, suppressing cohesion, and the like.
• Titanium black preferably has a small primary particle size and an average primary particle size of individual particles. Specifically, the average primary particle size is preferably 10 to 45 nm. Titanium black can also be used as a dispersion. For example, a dispersion containing titanium black particles and silica particles, in which the content ratio of Si atoms and Ti atoms in the dispersion is adjusted to a range of 0.20 to 0.50, may be mentioned. Regarding the dispersion, the description in paragraphs 0020 to 0105 of JP-A-2012-169556 can be referred to, and the contents thereof are incorporated herein.
• titanium black examples include titanium black 10S, 12S, 13R, 13M, 13M-C, 13R-N, 13M-T (trade name: manufactured by Mitsubishi Materials Corporation), Tilac D ( Trade name: manufactured by Ako Kasei Co., Ltd.) and the like.
• organic black colorants include bisbenzofuranone compounds, azomethine compounds, perylene compounds, and azo compounds, and bisbenzofuranone compounds and perylene compounds are preferred.
• the bisbenzofuranone compound JP-A-2010-534726, JP-A-2012-515233, JP-A-2012-515234, International Publication No. 2014/208348, JP-A-2015-525260, etc.
• perylene compounds for example, available as "Irgaphor Black” manufactured by BASF.
• a perylene compound C.I. I. Pigment Black 31, 32 and the like.
• the azomethine compound include compounds described in JP-A-01-170601, JP-A-02-034664, and the like.
• perylene black Liogen Black FK4280, etc.
• paragraphs 0016 to 0020 of JP-A-2017-226821 may be used as the organic black colorant.
• the coloring composition according to the present disclosure may contain one type of other coloring agent alone, or may contain two or more types thereof. When two or more types are used, the total amount thereof is preferably within the following range.
• the content of other coloring agents is preferably 1% by mass to 75% by mass relative to the total solid content of the coloring composition.
• the upper limit is more preferably 70% by mass or less, and even more preferably 65% by mass or less.
• the lower limit is more preferably 2% by mass or more, and even more preferably 5% by mass or more.
• the coloring composition according to the present disclosure further contains a green coloring agent in addition to the compound represented by Formula 1, it is preferably used as a coloring composition for forming green pixels of color filters.
• the other coloring agent may include a yellow coloring agent in addition to the green coloring agent, or may be only the green coloring agent.
• a yellow coloring agent containing a compound represented by Formula 1 and a green coloring agent are used in combination as a coloring agent, the content of the green coloring agent as another coloring agent is, with respect to 100 parts by mass of the yellow coloring agent, It is preferably 10 parts by mass to 1,000 parts by mass.
• the upper limit is more preferably 500 parts by mass or less, particularly preferably 300 parts by mass or less.
• the lower limit is more preferably 20 parts by mass or more, particularly preferably 30 parts by mass or more.
• a coloring composition according to the present disclosure contains a solvent.
• An organic solvent is mentioned as a solvent.
• the type of solvent is basically not particularly limited as long as it satisfies the solubility of each component and the coatability of the composition.
• Organic solvents include ester-based solvents, ketone-based solvents, alcohol-based solvents, amide-based solvents, ether-based solvents, and hydrocarbon-based solvents. For these details, reference can be made to paragraph 0223 of WO2015/166779, the content of which is incorporated herein. Ester-based solvents substituted with cyclic alkyl groups and ketone-based solvents substituted with cyclic alkyl groups 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, ethylcarbitol Acetate, butyl carbitol acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, 3-methoxy-N,N-dimethylpropanamide, 3-butoxy-N
• aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, etc.) as organic solvents may be better reduced for environmental reasons (e.g., 50 mass ppm (parts per million), 10 mass ppm or less, or 1 mass ppm or less).
• an organic solvent with a low metal content it is preferable to use an organic solvent with a low metal content.
• the metal content of the organic solvent is preferably, for example, 10 mass ppb (parts per billion) or less. If necessary, an organic solvent at a ppt (parts per trillion) level by mass may be used, and such an organic solvent is provided, for example, by Toyo Gosei Co., Ltd. (Chemical Daily, November 13, 2015). .
• Examples of methods for removing impurities such as metals from organic solvents include distillation (molecular distillation, thin film distillation, etc.) and filtration using a filter.
• the filter pore size of the filter used for filtration is preferably 10 ⁇ m or less, more preferably 5 ⁇ m or less, and even more preferably 3 ⁇ m or less.
• the material of the filter is preferably polytetrafluoroethylene, polyethylene or nylon.
• the organic solvent may contain isomers (compounds with the same number of atoms but different structures). Moreover, only one isomer may be contained, or a plurality of isomers may be contained.
• the content of peroxide in the organic solvent is preferably 0.8 mmol/L or less, and more preferably substantially free of peroxide.
• the content of the solvent in the coloring composition is preferably from 10% by mass to 95% by mass, more preferably from 20% by mass to 90% by mass, and further from 30% by mass to 90% by mass. preferable.
• the colored composition according to the present disclosure does not substantially contain environmentally regulated substances from the viewpoint of environmental regulations.
• substantially free of environmentally regulated substances means that the content of environmentally regulated substances in the colored composition is 50 ppm by mass or less, preferably 30 ppm by mass or less. , is more preferably 10 mass ppm or less, and particularly preferably 1 mass ppm or less.
• Environmental control substances include, for example, benzene; alkylbenzenes such as toluene and xylene; and halogenated benzenes such as chlorobenzene.
• distillation off a small amount of environmentally regulated substances it is also useful to azeotrope with a solvent having a boiling point equivalent to that of the solvent in order to increase the efficiency.
• a polymerization inhibitor or the like is added and distilled off under reduced pressure in order to suppress the radical polymerization reaction from progressing during the vacuum distillation and the intermolecular cross-linking.
• These distillation methods are the raw material stage, the reaction product of the raw materials (for example, the resin solution or polyfunctional monomer solution after polymerization), or the colored composition stage produced by mixing these compounds. It is possible at any stage such as
• the coloring composition according to the present disclosure can contain pigment derivatives.
• Pigment derivatives are used, for example, as dispersing aids.
• Pigment derivatives include compounds having a structure in which an acid group or a basic group is bonded to a pigment skeleton.
• Dye skeletons constituting pigment derivatives include quinoline dye skeletons, benzimidazolone dye skeletons, benzoisoindole dye skeletons, benzothiazole dye skeletons, iminium dye skeletons, squarylium dye skeletons, croconium dye skeletons, oxonol dye skeletons, and pyrrolopyrrole dye skeletons.
• diketopyrrolopyrrole dye skeleton azo dye skeleton, azomethine dye skeleton, phthalocyanine dye skeleton, naphthalocyanine dye skeleton, anthraquinone dye skeleton, quinacridone dye skeleton, dioxazine dye skeleton, perinone dye skeleton, perylene dye skeleton, thioindigo dye skeleton, Isoindoline dye skeletons, isoindolinone dye skeletons, quinophthalone dye skeletons, iminium dye skeletons, dithiol dye skeletons, triarylmethane dye skeletons, pyrromethene dye skeletons, and the like can be mentioned.
• the acid group includes a carboxy group, a sulfo group, a phosphoric acid group, a boronic acid group, a carboxylic acid amide group, a sulfonic acid amide group, an imidic acid group and salts thereof.
• Atoms or atomic groups constituting the salt include alkali metal ions (Li + , Na + , K + etc.), alkaline earth metal ions (Ca 2+ , Mg 2+ etc.), ammonium ions, imidazolium ions, pyridinium ions, phosphonium ion and the like.
• the carboxylic acid amide group a group represented by —NHCOR X1 is preferable.
• sulfonic acid amide group a group represented by —NHSO 2 R X2 is preferable.
• the imidic acid group is preferably a group represented by —SO 2 NHSO 2 R X3 , —CONHSO 2 R X4 , —CONHCOR X5 or SO 2 NHCOR X6 , more preferably —SO 2 NHSO 2 R X3 .
• R X1 to R X6 each independently represent an alkyl group or an aryl group.
• the alkyl groups and aryl groups represented by R X1 to R X6 may have substituents.
• the substituent is preferably a halogen atom, more preferably a fluorine atom.
• Basic groups include amino groups, pyridinyl groups and salts thereof, salts of ammonium groups, and phthalimidomethyl groups.
• Atoms or atomic groups constituting salts include hydroxide ions, halogen ions, carboxylate ions, sulfonate ions, and phenoxide ions.
• a pigment derivative having excellent visible transparency (hereinafter also referred to as a transparent pigment derivative) can also be used as the pigment derivative.
• the maximum molar extinction coefficient ( ⁇ max) of the transparent pigment derivative in the wavelength region of 400 nm to 700 nm is preferably 3,000 L ⁇ mol ⁇ 1 ⁇ cm ⁇ 1 or less, more preferably 1,000 L ⁇ mol ⁇ 1 ⁇ cm ⁇ It is more preferably 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 compounds described in JP-A-56-118462, compounds described in JP-A-63-264674, compounds described in JP-A-01-217077, JP-A-03- Compounds described in JP-A-009961, compounds described in JP-A-03-026767, compounds described in JP-A-03-153780, compounds described in JP-A-03-045662, JP-A-04-285669 Compounds described in publications, compounds described in JP-A-06-145546, compounds described in JP-A-06-212088, compounds described in JP-A-06-240158, JP-A-10-030063 Compounds described, compounds described in JP-A-10-195326, compounds described in paragraphs 0086 to 0098 of WO 2011/024896, WO 2012/102399 described in paragraphs 0063 to 0094 Compounds, compounds described in paragraph number 0082 of WO 2017/038252, compounds described in paragraph number 0171 of JP
• the content of the pigment derivative is preferably 1 to 30 parts by mass, more preferably 3 to 20 parts by mass, with respect to 100 parts by mass of the colorant.
• the total content of the pigment derivative and the colorant is preferably 35% by mass or more, more preferably 40% by mass or more, and even more preferably 45% by mass or more, relative to the total solid content of the coloring composition. , 50% by mass or more is particularly preferred.
• the upper limit is preferably 70% by mass or less, more preferably 65% by mass or less. Only one pigment derivative may be used, or two or more pigment derivatives may be used in combination.
• Colored compositions according to the present disclosure may also contain polyalkyleneimines.
• Polyalkyleneimines are used, for example, as dispersing aids for pigments.
• a dispersing aid is a material for enhancing dispersibility of a pigment in a coloring composition.
• a polyalkyleneimine is a polymer obtained by ring-opening polymerization of an alkyleneimine and has at least a secondary amino group.
• the polyalkyleneimine may contain primary amino groups or tertiary amino groups in addition to secondary amino groups.
• the polyalkyleneimine is preferably a polymer having a branched structure each 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, still 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 when the molecular weight can be calculated from the structural formula, 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 value of the number average molecular weight measured by the boiling point elevation method is used.
• the value of the number average molecular weight measured by the viscosity method is used.
• the value of the number average molecular weight in terms of polystyrene measured by the 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.
• alkyleneimine examples include ethyleneimine, propyleneimine, 1,2-butyleneimine, 2,3-butyleneimine and the like, preferably ethyleneimine or propyleneimine, more preferably ethyleneimine. preferable. It is particularly preferred that the polyalkyleneimine is polyethyleneimine. Further, the polyethyleneimine preferably contains 10 mol% or more, more preferably 20 mol% or more, of the primary amino group with respect to the total of the primary amino group, the secondary amino group and the tertiary amino group. , more preferably 30 mol % or more.
• Commercial products of polyethyleneimine include Epomin SP-003, SP-006, SP-012, SP-018, SP-200, P-1000 (manufactured by Nippon Shokubai Co., Ltd.).
• the content of the polyalkyleneimine in the total solid content of the coloring composition is preferably 0.1% by mass to 5% by mass.
• the lower limit is more preferably 0.2% by mass or more, still more preferably 0.5% by mass or more, and particularly preferably 1% by mass or more.
• the upper limit is more preferably 4.5% by mass or less, even more preferably 4% by mass or less, and particularly preferably 3% by mass or less.
• the content of the polyalkyleneimine is preferably 0.5 parts by mass to 20 parts by mass with respect to 100 parts by mass of the pigment.
• the lower limit is more preferably 0.6 parts by mass or more, still more preferably 1 part by mass or more, and particularly preferably 2 parts by mass or more.
• the upper limit is more preferably 10 parts by mass or less, and even more preferably 8 parts by mass or less. Only one kind of polyalkyleneimine may be used, or two or more kinds thereof may be used. When two or more types are used, the total amount thereof is preferably within the above range.
• a colored composition according to the present disclosure may contain a curing accelerator.
• Curing accelerators include thiol compounds, methylol compounds, amine compounds, phosphonium salt compounds, amidine salt compounds, amide compounds, base generators, isocyanate compounds, alkoxysilane compounds, onium salt compounds and the like.
• the curing accelerator include compounds described in paragraph numbers 0094 to 0097 of WO 2018/056189, compounds described in paragraph numbers 0246 to 0253 of JP 2015-034963, JP 2013-041165 Compounds described in paragraph numbers 0186 to 0251 of the publication, ionic compounds described in JP 2014-055114, compounds described in paragraph numbers 0071 to 0080 of JP 2012-150180, JP 2011-253054 Alkoxysilane compounds having an epoxy group described in JP-A-2005-200157, compounds described in paragraphs 0085 to 0092 of Japanese Patent No. 5765059, and carboxy group-containing epoxy curing agents described in JP-A-2017-036379.
• the content of the curing accelerator in the total solid content of the coloring composition is preferably 0.3 wt% to 8.9 wt%, more preferably 0.8 wt% to 6.4 wt% .
• a colored composition according to the present disclosure may contain an infrared absorbing agent.
• the infrared absorbing agent is preferably a compound having a maximum absorption wavelength on the longer wavelength side than the wavelength of 700 nm.
• the infrared absorbing agent is preferably a compound having a maximum absorption wavelength in the wavelength range of more than 700 nm and 1800 nm or less.
• the ratio A 1 /A 2 between the absorbance A 1 at a wavelength of 500 nm and the absorbance A 2 at the maximum absorption wavelength of the infrared absorbent is preferably 0.08 or less, more preferably 0.04 or less. .
• infrared absorbers examples 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, and azomethine. compounds, anthraquinone compounds, dibenzofuranone compounds, dithiolene metal complexes, metal oxides, metal borides, and the like.
• pyrrolopyrrole compound compounds described in paragraph numbers 0016 to 0058 of JP-A-2009-263614, compounds described in paragraph numbers 0037-0052 of JP-A-2011-068731, WO 2015/166873 Compounds described in Paragraph Nos. 0010 to 0033 and the like.
• examples of the squarylium compound include compounds described in paragraph numbers 0044 to 0049 of JP-A-2011-208101, compounds described in paragraph numbers 0060 to 0061 of Japanese Patent No. 6065169, and paragraph number 0040 of WO 2016/181987.
• Examples of croconium compounds include compounds described in JP-A-2017-082029.
• As the iminium compound for example, compounds described in JP-A-2008-528706, compounds described in JP-A-2012-012399, compounds described in JP-A-2007-092060, International Publication No. 2018/043564 and the compounds described in paragraphs 0048 to 0063 of.
• Examples of the phthalocyanine compound include compounds described in paragraph number 0093 of JP-A-2012-077153, oxytitanium phthalocyanine described in JP-A-2006-343631, and paragraph numbers 0013 to 0029 of JP-A-2013-195480. compounds, vanadium phthalocyanine compounds described in Japanese Patent No. 6081771, vanadium phthalocyanine compounds described in International Publication No. 2020/071486, and phthalocyanine compounds described in International Publication No. 2020/071470. Examples of naphthalocyanine compounds include compounds described in paragraph number 0093 of JP-A-2012-077153. Dithiolene metal complexes include compounds described in Japanese Patent No. 5733804.
• metal oxides include indium tin oxide, antimony tin oxide, zinc oxide, Al-doped zinc oxide, fluorine-doped tin dioxide, niobium-doped titanium dioxide, and tungsten oxide.
• metal borides include lanthanum boride.
• Commercially available lanthanum boride products include LaB 6 -F (manufactured by Nippon New Metal Co., Ltd.).
• a metal boride the compound as described in international publication 2017/119394 can also be used.
• commercially available products of indium tin oxide include F-ITO (manufactured by DOWA Hitech Co., Ltd.).
• the infrared absorbing agent the squarylium compound described in JP-A-2017-197437, the squarylium compound described in JP-A-2017-025311, the squarylium compound described in WO 2016/154782, and the patent No. 5884953. No. 6036689, squarylium compounds described in Japanese Patent No. 5810604, squarylium compounds described in paragraphs 0090 to 0107 of International Publication No.
• the content of the infrared absorbing agent in the total solid content of the coloring composition is preferably 1% by mass to 40% by mass.
• the lower limit is more preferably 2% by mass or more, still more preferably 5% by mass or more, and particularly preferably 10% by mass or more.
• the upper limit is more preferably 30% by mass or less, and even more preferably 25% by mass or less.
• the coloring composition according to the present disclosure may contain only one type of infrared absorber, or may contain two or more types. When two or more kinds of infrared absorbing agents are included, the total amount thereof is preferably within the above range.
• a colored composition according to the present disclosure 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, and triazine compounds. Specific examples of such compounds include paragraph numbers 0038 to 0052 of JP-A-2009-217221, paragraph numbers 0052-0072 of JP-A-2012-208374, and paragraph numbers 0317-0317 of JP-A-2013-068814.
• UV absorbers examples include UV-503 (manufactured by Daito Chemical Co., Ltd.), Tinuvin series and Uvinul series manufactured by BASF, and Sumisorb series manufactured by Sumika Chemtex Co., Ltd. .
• Benzotriazole compounds include the MYUA series manufactured by Miyoshi Oil (Kagaku Kogyo Nippo, February 1, 2016).
• the ultraviolet absorber is a compound described in paragraph numbers 0049 to 0059 of Japanese Patent No.
• a thioaryl group-substituted benzotriazole-type ultraviolet absorber described in can also be used.
• the content of the ultraviolet absorber in the total solid content of the coloring composition is preferably 0.01% by mass to 10% by mass, more preferably 0.01% by mass to 5% by mass. Only one type of ultraviolet absorber may be used, or two or more types may be used. When two or more are used, the total amount thereof is preferably within the above range.
• the coloring composition according to the present disclosure can contain a polymerization inhibitor.
• Polymerization inhibitors include hydroquinone, p-methoxyphenol, di-tert-butyl-p-cresol, pyrogallol, tert-butylcatechol, benzoquinone, 4,4′-thiobis(3-methyl-6-tert-butylphenol), 2,2′-methylenebis(4-methyl-6-t-butylphenol), 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% by mass to 5% by mass. Only one kind of polymerization inhibitor may be used, or two or more kinds thereof may be used. When two or more types are used, the total amount thereof is preferably within the above range.
• the coloring composition according to the present disclosure can contain a silane coupling agent.
• a silane coupling agent means a silane compound having a hydrolyzable group and other functional groups.
• the hydrolyzable group refers to a substituent that is directly bonded to a silicon atom and capable of forming a siloxane bond by at least one of hydrolysis reaction and condensation reaction.
• Hydrolyzable groups include, for example, halogen atoms, alkoxy groups, acyloxy groups and the like, with alkoxy groups being preferred. That is, the silane coupling agent is preferably a compound having an alkoxysilyl group.
• Examples of functional groups other than hydrolyzable groups include vinyl group, (meth)allyl group, (meth)acryloyl group, mercapto group, epoxy group, oxetanyl group, amino group, ureido group, sulfide group and isocyanate group. , phenyl group, etc., and amino group, (meth)acryloyl group and epoxy group are preferred.
• silane coupling agent examples include N- ⁇ -aminoethyl- ⁇ -aminopropylmethyldimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-602), N- ⁇ -aminoethyl- ⁇ -amino propyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-603), N- ⁇ -aminoethyl- ⁇ -aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBE-602), ⁇ -aminopropyltrimethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM-903), ⁇ -aminopropyltriethoxysilane (manufactured by Shin-Etsu Chemical Co., Ltd., trade name KBM
• silane coupling agent examples include compounds described in paragraph numbers 0018 to 0036 of JP-A-2009-288703 and compounds described in paragraph numbers 0056-0066 of JP-A-2009-242604. , the contents of which are incorporated herein.
• the content of the silane coupling agent in the total solid content of the coloring composition is preferably 0.01% by mass to 15.0% by mass, and 0.05% by mass to 10.0% by mass. more preferred. Only one kind of silane coupling agent may be used, or two or more kinds thereof may be used. When two or more types are used, the total amount thereof is preferably within the above range.
• a coloring composition according to the present disclosure may contain a surfactant.
• a surfactant various surfactants such as fluorine-based surfactants, nonionic surfactants, cationic surfactants, anionic surfactants and silicone surfactants can be used.
• the surfactant is preferably a silicone-based surfactant or a fluorine-based surfactant.
• surfactants reference can be made to surfactants described in paragraphs 0238-0245 of WO2015/166779, the contents of which are incorporated herein.
• the fluorine content in the fluorosurfactant is preferably 3% to 40% by mass, more preferably 5% to 30% by mass, and particularly preferably 7% to 25% by mass.
• a fluorine-based surfactant having a fluorine content within this range is effective in uniformity of the thickness of the coating film and saving liquid, and has good solubility in the coloring composition.
• JP 2014-041318 Paragraph Nos. 0060 to 0064 (corresponding International Publication No. 2014/017669 Paragraph Nos. 0060 to 0064) surfactants described in, JP 2011- Examples include surfactants described in paragraphs 0117 to 0132 of JP-A-132503 and surfactants described in JP-A-2020-008634, the contents of which are incorporated herein.
• Examples of commercially available fluorosurfactants include MEGAFACE F-171, F-172, F-173, F-176, F-177, F-141, F-142, F-143, and F-144.
• the fluorine-based surfactant has a molecular structure with a functional group containing a fluorine atom, and an acrylic compound in which the functional group containing a fluorine atom is cleaved and the fluorine atom volatilizes when heat is applied is also suitable.
• fluorine-based surfactants include Megafac DS series manufactured by DIC Corporation (Chemical Daily (February 22, 2016), Nikkei Sangyo Shimbun (February 23, 2016)), for example, Mega Fac DS-21.
• fluorosurfactant it is also preferable to use a polymer of a fluorine atom-containing vinyl ether compound having a fluorinated alkyl group or a fluorinated alkylene ether group and a hydrophilic vinyl ether compound as the fluorosurfactant.
• fluorosurfactants include fluorosurfactants described in JP-A-2016-216602, the contents of which are incorporated herein.
• a block polymer can also be used for the fluorine-based surfactant.
• the fluorosurfactant has 2 or more (preferably 5 or more) repeating units derived from a (meth)acrylate compound having a fluorine atom and an alkyleneoxy group (preferably an ethyleneoxy group or a propyleneoxy group) (meta).
• a fluorine-containing polymer compound containing a repeating unit derived from an acrylate compound can also be preferably used.
• fluorine-containing surfactants described in paragraphs 0016 to 0037 of JP-A-2010-032698 and the following compounds are also exemplified as fluorine-based surfactants used in the present disclosure.
• the weight average molecular weight of the above compound is preferably 3,000 to 50,000, for example, 14,000.
• % indicating the ratio of repeating units is mol %.
• a fluoropolymer having an ethylenically unsaturated group in a side chain can also be used as the fluorosurfactant.
• Specific examples include compounds described in paragraph numbers 0050 to 0090 and paragraph numbers 0289 to 0295 of JP-A-2010-164965, MEGAFACE RS-101, RS-102 and RS-718K manufactured by DIC Corporation, and RS-72-K.
• compounds described in paragraphs 0015 to 0158 of JP-A-2015-117327 can also be used.
• m represents 1 or 2
• n represents an integer of 1 to 4
• a represents 1 or 2
• X a + is a valent metal ion, primary ammonium ion, Represents secondary ammonium ion, tertiary ammonium ion, quaternary ammonium ion or NH4 + .
• Nonionic surfactants include glycerol, trimethylolpropane, trimethylolethane and their ethoxylates and propoxylates (e.g., glycerol propoxylate, glycerol ethoxylate, etc.), polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, Polyoxyethylene oleyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene nonylphenyl ether, polyethylene glycol dilaurate, polyethylene glycol distearate, sorbitan fatty acid ester, Pluronic L10, L31, L61, L62, 10R5, 17R2, 25R2 (BASF company), Tetronic 304, 701, 704, 901, 904, 150R1 (manufactured by BASF), Solsperse 20000 (manufactured by Nippon Lubrizol Co., Ltd.), NCW-101, NCW-1001, NCW-1002 (Fuji
• Silicone surfactants include DOWSIL SH8400, SH8400 FLUID, FZ-2122, 67 Additive, 74 Additive, M Additive, SF 8419 OIL (manufactured by Dow Toray Industries, Inc.), TSF-4300, TSF-4445, TSF-4460, TSF-4452 (manufactured by Momentive Performance Materials), KP-341, KF-6000, KF-6001, KF-6002, KF-6003 (manufactured by Shin-Etsu Chemical Co., Ltd.) , BYK-307, BYK-322, BYK-323, BYK-330, BYK-333, BYK-3760, BYK-UV3510 (manufactured by BYK-Chemie) and the like.
• a compound with the following structure can also be used as a silicone-based surfactant.
• the content of the surfactant in the total solid content of the coloring composition is preferably 0.001% by mass to 5.0% by mass, more preferably 0.005% by mass to 3.0% by mass. preferable. Only one type of surfactant 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.
• a coloring composition according to the present disclosure may contain an antioxidant.
• Antioxidants include phenol compounds, phosphite ester compounds, thioether compounds and the like. Any phenolic compound known as a phenolic antioxidant can be used as the phenolic compound. Preferred phenolic compounds include hindered phenolic compounds. A compound having a substituent at a site adjacent to the phenolic hydroxy group (ortho position) is preferred. A substituted or unsubstituted alkyl group having 1 to 22 carbon atoms is preferable as the above substituent.
• the antioxidant is also preferably a compound having a phenol group and a phosphite ester group in the same molecule.
• Phosphorus-based antioxidants can also be suitably used as antioxidants.
• a phosphorus antioxidant 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, ethyl bis(2,4-di-tert-butyl-6-methylphenyl) phosphite, and the like.
• antioxidants examples include Adekastab AO-20, Adekastab AO-30, Adekastab AO-40, Adekastab AO-50, Adekastab AO-50F, Adekastab AO-60, Adekastab AO-60G, Adekastab AO-80. , ADEKA STAB AO-330 (manufactured by ADEKA Corporation) and the like.
• antioxidants are compounds described in paragraph numbers 0023 to 0048 of Japanese Patent No. 6268967, compounds described in WO 2017/006600, compounds described in WO 2017/164024, Compounds described in Korean Patent Publication No. 10-2019-0059371 can also be used.
• the content of the antioxidant in the total solid content of the coloring composition is preferably 0.01% by mass to 20% by mass, more preferably 0.3% by mass to 15% by mass. Only one kind of antioxidant may be used, or two or more kinds thereof may be used. When two or more kinds are used, it is preferable that the total amount thereof is within the above range.
• the coloring composition according to the present disclosure may optionally contain sensitizers, curing accelerators, fillers, thermosetting accelerators, plasticizers and other auxiliaries (e.g., conductive particles, antifoaming agents, flame retardants, , leveling agents, release accelerators, fragrances, surface tension modifiers, chain transfer agents, etc.). Properties such as film physical properties can be adjusted by appropriately containing these components. These components are, for example, described in JP 2012-003225, paragraph number 0183 and later (corresponding US Patent Application Publication No. 2013/0034812, paragraph number 0237), JP 2008-250074 paragraph The descriptions of numbers 0101 to 0104, 0107 to 0109, etc. can be referred to, and the contents thereof are incorporated herein.
• auxiliaries e.g., conductive particles, antifoaming agents, flame retardants, , leveling agents, release accelerators, fragrances, surface tension modifiers, chain transfer agents, etc.
• the colored composition according to the present disclosure may contain latent antioxidants, if desired.
• the latent antioxidant is a compound in which the site functioning as an antioxidant is protected with a protective group, and is heated at 100°C to 250°C, or at 80°C to 200°C in the presence of an acid/base catalyst. Examples thereof include compounds whose protective groups are eliminated by heating to function as antioxidants. Examples of latent antioxidants include compounds described in International Publication No. 2014/021023, International Publication No. 2017/030005, and JP-A-2017-008219. Commercially available latent antioxidants include ADEKA Arkles GPA-5001 (manufactured by ADEKA Co., Ltd.).
• the coloring composition according to the present disclosure may contain metal oxides to adjust the refractive index of the resulting film.
• metal oxides include TiO 2 , ZrO 2 , Al 2 O 3 and SiO 2 .
• the primary particle size of the metal oxide is preferably 1 nm to 100 nm, more preferably 3 nm to 70 nm, even more preferably 5 nm to 50 nm.
• Metal oxides may have a core-shell structure. Moreover, in this case, the core portion may be hollow.
• the coloring composition according to the present disclosure may contain a light resistance improver.
• a light resistance improver compounds described in paragraph numbers 0036 to 0037 of JP-A-2017-198787, compounds described in paragraph numbers 0029-0034 of JP-A-2017-146350, JP-A-2017-129774 Compounds described in paragraph numbers 0036 to 0037, 0049 to 0052 of JP 2017-129674 JP 2017-129674 paragraph numbers 0031 to 0034, 0058 to 0059 compounds described in JP 2017-122803 JP 2017-122803 paragraph numbers 0036 to 0037 , compounds described in 0051 to 0054, compounds described in paragraph numbers 0025 to 0039 of WO 2017/164127, compounds described in paragraph numbers 0034 to 0047 of JP 2017-186546, JP 2015-025116 Compounds described in paragraph numbers 0019 to 0041 of JP-A-2012-145604, compounds described in paragraph numbers 0101-0125 of JP-A
• the coloring composition according to the present disclosure is substantially free of terephthalate.
• substantially free means that the content of terephthalic acid ester is 1,000 mass ppb or less in the total amount of the coloring composition, and more preferably 100 mass ppb or less. It is preferred, and zero is particularly preferred.
• perfluoroalkylsulfonic acid and its salts may be regulated.
• perfluoroalkylsulfonic acid especially perfluoroalkylsulfonic acid having 6 to 8 carbon atoms in the perfluoroalkyl group
• the content of perfluoroalkylcarboxylic acid especially perfluoroalkylcarboxylic acid having 6 to 8 carbon atoms in the perfluoroalkyl group
• the content of perfluoroalkylcarboxylic acid (especially perfluoroalkylcarboxylic acid having 6 to 8 carbon atoms in the perfluoroalkyl group) and its salt is 0.01 ppb to 1,000ppb to 1,000ppb to the total solid content of the coloring composition.
• the coloring composition according to the present disclosure may be substantially free of perfluoroalkylsulfonic acid and its salts and perfluoroalkylcarboxylic acid and its salts.
• a compound that can substitute for perfluoroalkylsulfonic acid and its salt and a compound that can substitute for perfluoroalkylcarboxylic acid and its salt, perfluoroalkylsulfonic acid and its salt, and perfluoroalkylcarboxylic acid and salts thereof may be selected.
• Examples of compounds that can substitute for regulated compounds include compounds that are excluded from the scope of regulation due to differences in the number of carbon atoms in perfluoroalkyl groups. However, the above content does not prevent the use of perfluoroalkylsulfonic acid and its salts, and perfluoroalkylcarboxylic acid and its salts.
• the coloring composition according to the present disclosure may contain perfluoroalkylsulfonic acid and its salts and perfluoroalkylcarboxylic acid and its salts within the maximum permissible range.
• the water content of the coloring composition according to the present disclosure is preferably 3% by mass or less, more preferably 0.01% by mass to 1.5% by mass, and in the range of 0.1% by mass to 1.0% by mass. is more preferable.
• the water content can be measured by the Karl Fischer method.
• the coloring composition according to the present disclosure can be used by adjusting the viscosity for the purpose of adjusting the film surface state (such as flatness) and adjusting the film thickness.
• the viscosity value can be appropriately selected as necessary, and is preferably, for example, 0.3 mPa ⁇ s to 50 mPa ⁇ s, more preferably 0.5 mPa ⁇ s to 20 mPa ⁇ s at 25°C.
• a method for measuring the viscosity for example, a cone-plate type viscometer can be used, and the viscosity can be measured in a state where the temperature is adjusted to 25°C.
• the colored composition according to the present disclosure preferably has a chloride ion content of 10,000 ppm or less, preferably 1000 ppm or less, from the viewpoint of environmental friendliness, suppression of foreign matter generation, suppression of device contamination, etc. is more preferable.
• a chloride ion content 10,000 ppm or less, preferably 1000 ppm or less, from the viewpoint of environmental friendliness, suppression of foreign matter generation, suppression of device contamination, etc. is more preferable.
• the use of raw materials with a low chloride ion content, washing with water, ion exchange resin, a method of removing chloride ions by filter filtration, etc. be done.
• a known method can be used as a method for measuring chloride ions, and examples thereof include ion chromatography and combustion ion chromatography.
• the container for the coloring composition is not particularly limited, and known containers can be used.
• a storage container a multi-layer bottle whose inner wall is composed of 6 types and 6 layers of resins and a bottle with a 7-layer structure of 6 types of resins for the purpose of suppressing the contamination of raw materials and coloring compositions. It is also preferred to use Examples of such a container include the container described in JP-A-2015-123351.
• the inner wall of the container is preferably made of glass or stainless steel for the purpose of preventing metal elution from the inner wall of the container, enhancing the storage stability of the coloring composition, and suppressing deterioration of components.
• Coloring compositions according to the present disclosure can be prepared by mixing the aforementioned ingredients. In preparing the coloring composition, all components may be dissolved and / or dispersed in a solvent at the same time to prepare a coloring composition, and if necessary, each component may be appropriately prepared as two or more solutions or dispersions. , these may be mixed at the time of use (at the time of application) to prepare a colored composition.
• a process of dispersing the pigment when preparing the coloring composition.
• mechanical forces used for dispersing pigments include compression, squeezing, impact, shearing, cavitation, and the like.
• Specific examples of these processes include bead mills, sand mills, roll mills, ball mills, paint shakers, microfluidizers, high speed impellers, sand grinders, flow jet mixers, high pressure wet atomization, ultrasonic dispersion, and the like.
• 2015-157893 can be preferably used.
• the particles may be made finer in the salt milling step.
• Materials, equipment, processing conditions, etc. used in the salt milling step can be referred to, for example, Japanese Patent Application Laid-Open Nos. 2015-194521 and 2012-046629.
• Beads used for dispersion can be zirconia, agate, quartz, titania, tungsten carbide, silicon nitride, alumina, stainless steel, glass, or combinations thereof.
• an inorganic compound having a Mohs hardness of 2 or more can be used.
• the composition may contain 1 to 10000 ppm of the beads.
• any filter that has been conventionally used for filtration or the like can be used without particular limitation.
• fluororesins such as polytetrafluoroethylene (PTFE) and polyvinylidene fluoride (PVDF)
• polyamide resins such as nylon (eg nylon-6, nylon-6,6)
• polyolefin resins such as polyethylene and polypropylene (PP) (including high-density, ultra-high-molecular-weight polyolefin resin) and other materials.
• PP polypropylene
• nylon including high density polypropylene
• nylon including high density polypropylene
• the pore size of the filter is preferably 0.01 ⁇ m to 7.0 ⁇ m, more preferably 0.01 ⁇ m to 3.0 ⁇ m, even more preferably 0.05 ⁇ m to 0.5 ⁇ m. If the pore diameter of the filter is within the above range, fine foreign matter can be removed more reliably.
• the pore size of the filter reference can be made to the filter manufacturer's nominal value.
• Various filters provided by Nihon Pall Co., Ltd. (DFA4201NIEY, DFA4201NAEY, DFA4201J006P, etc.), Advantech Toyo Co., Ltd., Nippon Entegris Co., Ltd. (former Japan Microlith Co., Ltd.), Kitz Micro Filter Co., Ltd., etc. can be used as filters. .
• fibrous filter media include polypropylene fibers, nylon fibers, and glass fibers.
• Commercially available products include SBP type series (SBP008, etc.), TPR type series (TPR002, TPR005, etc.), and SHPX type series (SHPX003, etc.) manufactured by Roki Techno.
• filters When using filters, different filters (eg, a first filter and a second filter, etc.) may be combined. At that time, filtration with each filter may be performed only once, or may be performed twice or more. Also, filters with different pore sizes within the range described above may be combined. Alternatively, the filtration with the first filter may be performed only on the dispersion liquid, and after mixing other components, the filtration with the second filter may be performed. In addition, the filter can be appropriately selected according to the hydrophilicity/hydrophobicity of the composition.
• the cured product according to the present disclosure is a cured product obtained by curing the colored composition according to the present disclosure.
• the film according to the present disclosure is a film obtained from the colored composition according to the present disclosure, and is preferably a film obtained by curing the colored composition according to the present disclosure.
• Films according to the present disclosure can be used in optical filters such as color filters and infrared transmission filters. Specifically, it can be preferably used as a colored pixel of a color filter. Examples of colored pixels include red pixels, green pixels, blue pixels, magenta pixels, cyan pixels, and yellow pixels. Green pixels, red pixels, or blue pixels are preferred, and green pixels are preferred. is more preferred.
• the film thickness of the film according to the present disclosure can be appropriately adjusted according to the purpose, but is preferably 0.1 ⁇ m to 20 ⁇ m.
• the upper limit of the film thickness is more preferably 10 ⁇ m or less, still more preferably 5 ⁇ m or less, even more preferably 3 ⁇ m or less, and particularly preferably 1.5 ⁇ m or less.
• the lower limit of the film thickness is more preferably 0.2 ⁇ m or more, still more preferably 0.3 ⁇ m or more.
• a cured product according to the present disclosure or a film according to the present disclosure can be produced through a step of applying a coloring composition according to the present disclosure to a support.
• the film manufacturing method further includes a step of forming a pattern (pixels).
• a method for forming the pattern (pixels) includes a photolithography method and a dry etching method, and the photolithography method is preferable.
• Pattern formation by photolithography includes the steps of forming a coloring composition layer on a support using the coloring composition according to the present disclosure, patternwise exposing the coloring composition layer, and the coloring composition layer. and a step of developing and removing the unexposed portions to form a pattern (pixels). If necessary, a step of baking the coloring composition layer (pre-baking step) and a step of baking the developed pattern (pixels) (post-baking step) may be provided.
• the colored composition according to the present disclosure is used to form the colored composition layer on the support.
• the support is not particularly limited and can be appropriately selected depending on the application. Examples thereof include glass substrates and silicon substrates, and silicon substrates are preferred. Also, a charge-coupled device (CCD), a complementary metal oxide semiconductor (CMOS), a transparent conductive film, or the like may be formed on the silicon substrate.
• CCD charge-coupled device
• CMOS complementary metal oxide semiconductor
• the silicon substrate is formed with a black matrix that isolates each pixel.
• the silicon substrate may be provided with an underlying layer for improving adhesion with the upper layer, preventing diffusion of substances, or flattening the substrate surface.
• the underlayer may be formed using a composition obtained by removing the coloring agent from the colored composition described herein, or a composition containing the resin, polymerizable compound, surfactant, etc. described herein. good.
• the surface contact angle of the underlayer is preferably 20° to 70° when measured with diiodomethane. Further, it is preferably 30° to 80° when measured with water.
• a known method can be used as a method for applying the coloring composition.
• dropping method drop cast
• slit coating method spray method
• roll coating method spin coating
• methods described in publications inkjet
• ejection system printing ejection system printing such as nozzle jet, flexographic printing, screen printing, gravure printing, reverse offset printing, metal mask printing, etc. various printing methods; a transfer method using a mold or the like; and a nanoimprint method.
• the application method for inkjet is not particularly limited.
• the colored composition layer formed on the support may be dried (pre-baked). Pre-baking may not be performed when the film is manufactured by a low-temperature process.
• the pre-baking temperature is preferably 150° C. or lower, more preferably 120° C. or lower, and even more preferably 110° C. or lower.
• the lower limit can be, for example, 50° C. or higher, and can also be 80° C. or higher.
• the prebaking time is preferably 10 seconds to 300 seconds, more preferably 40 seconds to 250 seconds, and even more preferably 80 seconds to 220 seconds. Pre-baking can be performed using a hot plate, an oven, or the like.
• the colored composition layer is exposed in a pattern (exposure step).
• the colored composition layer can be exposed in a pattern by exposing through a mask having a predetermined mask pattern using a stepper exposure machine, a scanner exposure machine, or the like. Thereby, the exposed portion can be cured.
• Radiation (light) that can be used for exposure includes g-line, i-line, and the like.
• Light with a wavelength of 300 nm or less (preferably light with a wavelength of 180 nm to 300 nm) can also be used.
• Light having a wavelength of 300 nm or less includes KrF rays (wavelength: 248 nm), ArF rays (wavelength: 193 nm), etc., and KrF rays (wavelength: 248 nm) are preferred.
• a long-wave light source of 300 nm or more can also be used.
• the light when exposing, the light may be continuously irradiated and exposed, or may be irradiated and exposed in pulses (pulse exposure).
• pulse exposure is an exposure method in which exposure is performed by repeating light irradiation and rest in short-time (for example, millisecond level or less) cycles.
• the dose is, for example, preferably 0.03 J/cm 2 to 2.5 J/cm 2 , more preferably 0.05 J/cm 2 to 1.0 J/cm 2 .
• the oxygen concentration at the time of exposure can be selected as appropriate.
• the exposure may be performed under an oxygen-free atmosphere, or under a high-oxygen atmosphere with an oxygen concentration exceeding 21% by volume (for example, 22% by volume, 30% by volume, or 50% by volume).
• the exposure illuminance can be set as appropriate, and is preferably 1,000 W/m 2 to 100,000 W/m 2 (eg, 5,000 W/m 2 , 15,000 W/m 2 , or 35,000 W/m 2 , 000 W/m 2 ).
• the oxygen concentration and exposure illuminance may be appropriately combined.
• the illuminance may be 10,000 W/m 2 at an oxygen concentration of 10% by volume, and the illuminance may be 20,000 W/m 2 at an oxygen concentration of 35% by volume.
• the unexposed areas of the colored composition layer are removed by development to form a pattern (pixels).
• the development and removal of the unexposed portion of the colored composition layer can be performed using a developer.
• the unexposed portion of the colored composition layer in the exposure step is eluted into the developer, leaving only the photocured portion.
• the temperature of the developer is preferably 20° C. to 30° C., for example.
• the development time is preferably 20 seconds to 180 seconds. Further, in order to improve the residue removability, the step of shaking off the developer every 60 seconds and then supplying new developer may be repeated several times.
• the developer includes an organic solvent, an alkaline developer, etc., and an alkaline developer is preferably used.
• an alkaline developer an alkaline aqueous solution (alkali developer) obtained by diluting an alkaline agent with pure water is preferable.
• alkaline agents include ammonia, ethylamine, diethylamine, dimethylethanolamine, diglycolamine, diethanolamine, hydroxylamine, ethylenediamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, and tetrabutylammonium hydroxide.
• ethyltrimethylammonium hydroxide ethyltrimethylammonium hydroxide
• benzyltrimethylammonium hydroxide dimethylbis(2-hydroxyethyl)ammonium hydroxide
• choline pyrrole
• piperidine 1,8-diazabicyclo-[5.4.0]-7-undecene
• examples include organic alkaline compounds and inorganic alkaline compounds such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium hydrogen carbonate, sodium silicate and sodium metasilicate.
• a compound having a large molecular weight is preferable for the alkaline agent from the standpoint of environment and safety.
• the concentration of the alkaline agent in the alkaline aqueous solution is preferably 0.001% by mass to 10% by mass, more preferably 0.01% by mass to 1% by mass.
• the developer may further contain a surfactant. From the viewpoint of transportation and storage convenience, the developer may be produced once as a concentrated solution and then diluted to the required concentration when used. Although the dilution ratio is not particularly limited, it can be set, for example, in the range of 1.5 times to 100 times. It is also preferable to wash (rinse) with pure water after development. Rinsing is preferably carried out by supplying a rinsing solution to the developed colored composition layer while rotating the support on which the developed colored composition layer is formed.
• the nozzle for discharging the rinsing liquid from the central portion of the support to the peripheral portion of the support.
• the moving speed of the nozzle may be gradually decreased.
• Additional exposure processing and post-baking are post-development curing treatments for complete curing.
• the heating temperature in post-baking is, for example, preferably 100°C to 240°C, more preferably 200°C to 240°C.
• Post-baking can be performed continuously or batchwise using a heating means such as a hot plate, a convection oven (hot air circulating dryer), or a high-frequency heater so that the developed film satisfies the above conditions.
• the additional exposure process is performed, the light used for exposure preferably has a wavelength of 400 nm or less. Also, the additional exposure process may be performed by the method described in Korean Patent Publication No. 10-2017-0122130.
• Pattern formation by a dry etching method is a step of forming a colored composition layer on a support using the colored composition according to the present disclosure, and curing the entire colored composition layer to form a cured product layer.
• a step of forming a photoresist layer on the cured layer a step of exposing the photoresist layer in a pattern and then developing it to form a resist pattern; and dry etching using an etching gas.
• a mode in which heat treatment after exposure and heat treatment (post-baking treatment) after development are performed is desirable.
• pattern formation by a dry etching method descriptions in paragraphs 0010 to 0067 of JP-A-2013-064993 can be referred to, and the contents thereof are incorporated herein.
• optical element An optical element according to the present disclosure has a film according to the present disclosure.
• Optical elements include optical filters, lenses, prisms, reflectors, diffraction gratings, and the like. Among them, an optical filter is preferable. Types of optical filters include color filters and infrared transmission filters, and color filters are preferred.
• a color filter preferably has a film according to the present disclosure as its colored pixels.
• the film thickness of the film according to the present disclosure can be appropriately adjusted according to the purpose.
• the film thickness is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, and even more preferably 5 ⁇ m or less.
• the lower limit of the film thickness is preferably 0.1 ⁇ m or more, more preferably 0.2 ⁇ m or more, and even more preferably 0.3 ⁇ m or more.
• the width of pixels included in the optical filter is preferably 0.3 ⁇ m to 10.0 ⁇ m.
• the lower limit is more preferably 0.4 ⁇ m or more, still more preferably 0.5 ⁇ m or more, and particularly preferably 0.6 ⁇ m or more.
• the upper limit is more preferably 5.0 ⁇ m or less, still more preferably 2.0 ⁇ m or less, particularly preferably 1.0 ⁇ m or less, and most preferably 0.8 ⁇ m or less.
• the Young's modulus of the pixel is preferably 0.5 GPa to 20 GPa, more preferably 2.5 GPa to 15 GPa.
• Each pixel included in the optical filter preferably has high flatness.
• the pixel surface roughness Ra is preferably 100 nm or less, more preferably 40 nm or less, and even more preferably 15 nm or less. Although the lower limit is not specified, it is preferably 0.1 nm or more, for example.
• the surface roughness of a pixel can be measured using, for example, AFM (Atomic Force Microscope) Dimension 3100 manufactured by Veeco.
• the contact angle of water on the pixel can be appropriately set to a preferable value, and is typically in the range of 50° to 110°. The contact angle can be measured using, for example, a contact angle meter CV-DT-A type (manufactured by Kyowa Interface Science Co., Ltd.).
• the volume resistance value of the pixel is high.
• the volume resistance value of the pixel is preferably 10 9 ⁇ cm or more, more preferably 10 11 ⁇ cm or more.
• the upper limit is not specified, it is preferably 10 14 ⁇ cm or less, for example.
• the volume resistance value of the pixel can be measured using an ultra-high resistance meter 5410 (manufactured by Advantest).
• a protective layer may be provided on the surface of the film according to the present disclosure.
• the protective layer By providing the protective layer, it is possible to impart various functions such as blocking oxygen, reducing reflection, making the film hydrophilic and hydrophobic, and blocking light of a specific wavelength (ultraviolet rays, near-infrared rays, etc.).
• the thickness of the protective layer is preferably 0.01 ⁇ m to 10 ⁇ m, more preferably 0.1 ⁇ m to 5 ⁇ m.
• Examples of the method of forming the protective layer include a method of applying a protective layer-forming composition, a chemical vapor deposition method, and a method of adhering a molded resin with an adhesive.
• Components constituting the protective layer include (meth)acrylic resins, ene-thiol resins, polycarbonate resins, polyether resins, polyarylate resins, polysulfone resins, polyethersulfone resins, polyphenylene resins, polyarylene ether phosphine oxide resins, and polyimides.
• the protective layer preferably contains a polyol resin, SiO 2 and Si 2 N 4 .
• the protective layer preferably contains a (meth)acrylic resin and a fluororesin.
• the protective layer may optionally contain organic/inorganic particles, absorbers for light of specific wavelengths (e.g., ultraviolet rays, near-infrared rays, etc.), refractive index modifiers, antioxidants, adhesion agents, additives such as surfactants. may contain.
• organic/inorganic particles include polymeric 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, and titanium oxynitride. , magnesium fluoride, hollow silica, silica, calcium carbonate, barium sulfate, and the like.
• a known absorber can be used as the absorber for light of a specific wavelength.
• the content of these additives can be appropriately adjusted, but is preferably 0.1% by mass to 70% by mass, more preferably 1% by mass to 60% by mass, based on the total mass of the protective layer.
• the protective layer the protective layers described in paragraphs 0073 to 0092 of JP-A-2017-151176 can also be used.
• the optical filter may have a structure in which each pixel is embedded in a space partitioned by partition walls, for example, in a grid pattern.
• An image sensor according to the present disclosure has a membrane according to the present disclosure.
• Image sensors include solid-state imaging devices, X-ray imaging devices, organic thin-film imaging devices, and the like. Among them, it can be suitably used for a solid-state imaging device.
• a solid-state imaging device according to the present disclosure includes a film according to the present disclosure. The configuration of the solid-state imaging device is not particularly limited as long as it functions as a solid-state imaging device.
• Transfer electrodes made of polysilicon or the like, and a plurality of photodiodes forming the light-receiving area of a solid-state imaging device (such as a CCD (charge-coupled device) image sensor, a CMOS (complementary metal-oxide semiconductor) image sensor, etc.) on a substrate.
• a light-shielding film is provided on the photodiode and the transfer electrode so that only the light-receiving portion of the photodiode is opened. It has a device protective film with a thickness of 1.5 mm, and has a color filter on the device protective film.
• the color filter may have a structure in which each color pixel is embedded in a space partitioned by partition walls, for example, in a grid pattern.
• the partition wall preferably has a lower refractive index than each color pixel. Examples of imaging devices having such a structure include devices described in JP-A-2012-227478, JP-A-2014-179577, and International Publication No. 2018/043654.
• an ultraviolet absorption layer may be provided in the structure of the solid-state imaging device to improve light resistance.
• An imaging device including a solid-state imaging device according to the present disclosure can be used not only for digital cameras and electronic devices (mobile phones, etc.) having an imaging function, but also for in-vehicle cameras and surveillance cameras.
• An image display device includes a film according to the present disclosure.
• image display devices include liquid crystal display devices and organic electroluminescence display devices.
• electroluminescence display devices For a definition of an image display device and details of each image display device, see, for example, “Electronic Display Device (by Akio Sasaki, Industrial Research Institute, 1990)", “Display Device (by Junsho Ibuki, Sangyo Tosho ( Co., Ltd.) issued in 1989).
• Liquid crystal display devices are described, for example, in “Next Generation Liquid Crystal Display Technology (edited by Tatsuo Uchida, published by Kogyo Choukai Co., Ltd., 1994)".
• the present disclosure can be applied to various types of liquid crystal display devices described in the above “next generation liquid crystal display technology”.
• X represents N or CR 8
• R 1 to R 9 each independently represent a hydrogen atom or a monovalent substituent
• two or more of R 1 to R 9 combine to form a ring
• Preferred aspects of the compound represented by Formula 1 in the compound according to the present disclosure are the same as the preferred aspects of the compound represented by Formula 1 described above in the coloring composition.
• Pigment Red 264 (diketopyrrolopyrrole compound, red pigment) PR272: C.I. I. Pigment Red 272 (diketopyrrolopyrrole compound, red pigment) PY129: C.I. I. pigment yellow 129 PY139: C.I. I. Pigment Yellow 139 (isoindoline compound, yellow pigment) PY150: C.I. I. Pigment Yellow 150 (azo compound, yellow pigment) PY185: C.I. I. Pigment Yellow 185 (isoindoline compound, yellow pigment) PO71: C.I. I. Pigment Orange 71 (diketopyrrolopyrrole compound, orange pigment) PB15:6: C.I. I. Pigment Blue 15:6 (phthalocyanine compound, blue pigment)
• IR-1 a compound having the following structure
• (dispersant) B-1 Resin having the following structure (The numerical value attached to the main chain is the molar ratio, and the numerical value attached to the side chain is the number of repeating units. Weight average molecular weight: 24,000)
• B-7 Resin synthesized by the following method Flow an appropriate amount of nitrogen into a flask equipped with a reflux condenser, a dropping funnel and a stirrer, replace with a nitrogen atmosphere, and add 340 parts by mass of propylene glycol monomethyl ether acetate (PGMEA). and heated to 80° C. with stirring.
• PGMEA propylene glycol monomethyl ether acetate
• the obtained resin had a weight average molecular weight of 9,400, a dispersity of 1.89, and an acid value of 114 mgKOH/g.
• a coloring composition was produced by mixing the raw materials shown in Tables 13 to 21 below.
• C-2 Resin with the following structure (the numerical value attached to the main chain is the molar ratio. Weight average molecular weight 30,000)
• C-3 Resin with the following structure (the number attached to the side chain is the number of repeating units. Weight average molecular weight 14,600)
• C-4 Resin with the following structure (the numbers in the structure below represent the weight ratio of each repeating unit. Weight average molecular weight 10,600)
• a solution prepared by dissolving 30 parts by mass of 2,2-azobis(2,4-dimethylvaleronitrile) as a polymerization initiator in 160 parts by mass of 1-methoxy-2-propyl acetate was added dropwise over 5 hours. After the completion of the dropwise addition of the initiator solution, the temperature was maintained at 85° C. for 4 hours, and then cooled to room temperature to obtain a resin.
• the resulting resin had a weight average molecular weight of 10,600, a dispersity of 2.01, and an acid value of 43 mgKOH/g.
• D-2 A mixture of compounds having the following structure (a mixture in which the molar ratio of the left compound (hexafunctional (meth)acrylate compound) and the right compound (pentafunctional (meth)acrylate compound) is 7:3)
• D-4 Trimethylolpropane ethylene oxide-modified triacrylate (manufactured by Toagosei Co., Ltd., Aronix M-350)
• D-5 EBECRYL80 (manufactured by Daicel Allnex, amine-containing tetrafunctional acrylate)
• D-6 ethoxylated dipentaerythritol hexamethacrylate
• E-1 to E-4 compounds having the following structures E-5: 2,2′,4-tris(2-chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-diphenyl-1,1 '-Biimidazole
• F-1 KF-6001 (manufactured by Shin-Etsu Chemical Co., Ltd., silicone surfactant, carbinol-modified polydimethylsiloxane at both ends, hydroxy value 62 mgKOH/g)
• F-2 A compound having the following structure (weight average molecular weight: 14,000). In the following formulas, % indicating the ratio of repeating units is mol %.
• F-3 Futergent 208G (manufactured by NEOS, fluorosurfactant)
• F-4 BYK-330 (manufactured by BYK-Chemie, silicone surfactant)
• F-5 DOWSIL SH8400 FLUID (manufactured by Dow Toray Industries, Inc., silicone surfactant)
• G-1 compound having the following structure (ultraviolet absorber)
• G-2 compound with the following structure (compound with an epoxy group, weight average molecular weight 3500)
• G-3 EHPE3150 (manufactured by Daicel Corporation, 1,2-epoxy-4-(2-oxiranyl)cyclohexane adduct of 2,2′-bis(hydroxymethyl)-1-butanol)
• G-4 A compound having the following structure (silane coupling agent)
• G-5 3-methacryloxypropyltrimethoxysilane (KBM-503, manufactured by Shin-Etsu Chemical Co., Ltd., silane coupling agent)
• G-6 p-methoxyphenol (polymerization inhibitor)
• G-7 Adekastab AO-80 (manufactured by ADEKA Corporation, antioxidant)
• the film prepared above was irradiated with light of 100,000 Lux for 2,000 hours using a light resistance tester (super xenon weather meter SX75, manufactured by Suga Test Instruments Co., Ltd.) (total irradiation amount: 2 100 million Lux ⁇ hr).
• the transmittance of the film after light irradiation and its integrated value were measured, and the light resistance was evaluated according to the following criteria.
• B The integrated value of the transmittance of the film at a wavelength of 400 nm to 700 nm after light irradiation is 95% or more and less than 98% of the integrated value of the transmittance of the film before light irradiation at a wavelength of 400 nm to 700 nm.
• C The integrated value of the transmittance of the film at a wavelength of 400 nm to 700 nm after light irradiation is 93% or more and less than 95% of the integrated value of the transmittance of the film before light irradiation at a wavelength of 400 nm to 700 nm.
• D The integrated value of the transmittance of the film at a wavelength of 400 nm to 700 nm after light irradiation is 90% or more and less than 93% of the integrated value of the transmittance of the film before light irradiation at a wavelength of 400 nm to 700 nm.
• E The integrated value of the transmittance of the film at a wavelength of 400 nm to 700 nm after light irradiation is less than 90% of the integrated value of the transmittance of the film before light irradiation at a wavelength of 400 nm to 700 nm.
• B The viscosity increase rate of the coloring composition exceeds 5% and is 7.5% or less.
• C The viscosity increase rate of the coloring composition exceeds 7.5% and is 10% or less.
• D The viscosity increase rate of the coloring composition exceeds 10%.
• the colored compositions of Examples were able to form films (colored matter) with excellent light resistance compared to the colored compositions of Comparative Examples.
• the colored compositions of Examples were also excellent in stability over time.
• the compound (Y-5) in the dispersion liquid 62 used in Example 62, the compound (Y-29) ⁇ compound (Y-36) also in the coloring composition replaced with the coloring composition of Example 62 Similar results were obtained.

Landscapes

• Physics & Mathematics (AREA)
• General Physics & Mathematics (AREA)
• Chemical & Material Sciences (AREA)
• Optics & Photonics (AREA)
• Nonlinear Science (AREA)
• Organic Chemistry (AREA)
• Spectroscopy & Molecular Physics (AREA)
• Mathematical Physics (AREA)
• Crystallography & Structural Chemistry (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Engineering & Computer Science (AREA)
• Architecture (AREA)
• Structural Engineering (AREA)
• Optical Filters (AREA)
• Nitrogen Condensed Heterocyclic Rings (AREA)

Priority Applications (2)

Applications Claiming Priority (2)

Publications (1)

Family

ID=85507573

Family Applications (1)

Country Status (4)

Cited By (1)

Citations (2)

Family Cites Families (6)

• 2022
  • 2022-08-16 WO PCT/JP2022/030920 patent/WO2023037828A1/ja not_active Ceased
  • 2022-08-16 KR KR1020247002389A patent/KR102795450B1/ko active Active
  • 2022-08-16 JP JP2023546853A patent/JPWO2023037828A1/ja active Pending
  • 2022-08-23 TW TW111131743A patent/TW202311251A/zh unknown

Patent Citations (2)

Also Published As

Similar Documents

Legal Events