WO2024219340A1 - 光吸収フィルタ、光学フィルタ及びその製造方法、有機エレクトロルミネッセンス表示装置、無機エレクトロルミネッセンス表示装置及び液晶表示装置 - Google Patents

光吸収フィルタ、光学フィルタ及びその製造方法、有機エレクトロルミネッセンス表示装置、無機エレクトロルミネッセンス表示装置及び液晶表示装置 Download PDF

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WO2024219340A1
WO2024219340A1 PCT/JP2024/014884 JP2024014884W WO2024219340A1 WO 2024219340 A1 WO2024219340 A1 WO 2024219340A1 JP 2024014884 W JP2024014884 W JP 2024014884W WO 2024219340 A1 WO2024219340 A1 WO 2024219340A1
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Prior art keywords
group
light
resin
layer
filter
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PCT/JP2024/014884
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English (en)
French (fr)
Japanese (ja)
Inventor
伸隆 深川
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Fujifilm Corp
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Fujifilm Corp
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Priority to JP2025515208A priority Critical patent/JPWO2024219340A1/ja
Priority to CN202480025021.0A priority patent/CN121079620A/zh
Publication of WO2024219340A1 publication Critical patent/WO2024219340A1/ja
Priority to US19/353,641 priority patent/US20260036730A1/en
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    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/208—Filters for use with infrared or ultraviolet radiation, e.g. for separating visible light from infrared and/or ultraviolet radiation
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • 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
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional [2D] radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional [2D] radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/86—Arrangements for improving contrast, e.g. preventing reflection of ambient light
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/10—OLED displays
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/38—Devices specially adapted for multicolour light emission comprising colour filters or colour changing media [CCM]

Definitions

  • the present invention relates to a light absorbing filter, an optical filter and its manufacturing method, an organic electroluminescence display device, an inorganic electroluminescence display device, and a liquid crystal display device.
  • OLED organic electroluminescence
  • inorganic electroluminescence display devices inorganic EL display devices
  • liquid crystal display devices etc.
  • liquid crystal display devices are expanding year by year as space-saving image display devices with low power consumption. Because the liquid crystal panel that displays images is a non-emissive element that does not emit light, liquid crystal display devices are equipped with a backlight unit that is disposed behind the liquid crystal panel and supplies light to the liquid crystal panel.
  • OLED display devices are devices that display images by utilizing the spontaneous emission of OLED elements. Therefore, compared to various display devices such as liquid crystal display devices and plasma display devices, they have advantages such as a high contrast ratio, high color reproducibility, a wide viewing angle, high-speed response, and the possibility of being thin and lightweight. In addition to these advantages, OLED display devices are being actively researched and developed as next-generation display devices because of their flexibility.
  • An inorganic EL display device is a device that displays images by utilizing the spontaneous emission of inorganic EL elements as a fluorescent material instead of OLED elements in an OLED display device. Recent research has led to hopes that a display device superior to an OLED display device in terms of a larger screen and longer life may be realized.
  • Patent Document 1 describes a laminate in which a gas barrier layer made of a crystalline resin, having a thickness of 0.1 ⁇ m to 10 ⁇ m and an oxygen permeability of 60 cc/m2 ⁇ day ⁇ atm or less, is directly disposed on at least one side of a wavelength selective absorption layer containing a dye having a main absorption wavelength band in a specific wavelength range and an anti-fading agent for the dye.
  • a gas barrier layer made of a crystalline resin, having a thickness of 0.1 ⁇ m to 10 ⁇ m and an oxygen permeability of 60 cc/m2 ⁇ day ⁇ atm or less
  • Patent Document 2 describes a light-absorbing filter containing a resin, a dye containing a squaraine-based dye represented by the general formula (1) described in Patent Document 2, and a compound that generates radicals by ultraviolet irradiation.
  • the light-absorbing filter described in Patent Document 2 exhibits a high decolorization rate by ultraviolet irradiation, and is said to have high decolorization properties without almost any absorption (hereinafter also referred to as "secondary absorption") derived from a new colored structure accompanying decomposition of the dye by ultraviolet irradiation.
  • an object of the present invention is to provide a light absorbing filter having excellent adhesion.
  • Another object of one embodiment of the present invention is to provide a light-absorbing filter having excellent adhesion and decolorization properties, and an optical filter using this light-absorbing filter, the optical filter having light-absorbing sites and light-absorption-loss sites at desired positions, a method for manufacturing the same, and an OLED display device, an inorganic electroluminescence display device, and a liquid crystal display device each including the optical filter.
  • a light absorption filter including a wavelength selective absorption layer containing a dye and a resin A containing an acid group, and an adjacent layer disposed directly on at least one side of the wavelength selective absorption layer, the adhesion between the wavelength selective absorption layer and the adjacent layer can be effectively improved by configuring the light absorption filter such that the adjacent layer contains a resin containing a basic group.
  • the present invention was completed through further research based on this knowledge.
  • the wavelength selective absorption layer is The light absorbing filter according to ⁇ 1>, further comprising a compound B that forms a hydrogen bond with the acid group contained in the resin A and generates radicals when irradiated with ultraviolet light.
  • ⁇ 4> An optical filter obtained by exposing the light absorbing filter according to ⁇ 2> or ⁇ 3> to ultraviolet light using a mask.
  • ⁇ 5> An organic electroluminescence display device, an inorganic electroluminescence display device, or a liquid crystal display device, comprising the optical filter according to ⁇ 4>.
  • ⁇ 6> The organic electroluminescent display device, inorganic electroluminescent display device, or liquid crystal display device according to ⁇ 5>, further comprising a layer for inhibiting light absorption of the compound B that generates radicals when irradiated with ultraviolet light, on a viewer's side with respect to the optical filter.
  • a method for producing an optical filter comprising irradiating the light absorbing filter according to ⁇ 2> or ⁇ 3> with ultraviolet light and exposing it to a mask.
  • substituents when there are a plurality of substituents or linking groups, etc., represented by a specific symbol or formula (hereinafter referred to as substituents, etc.), or when a plurality of substituents, etc., are specified at the same time, unless otherwise specified, the respective substituents, etc. may be the same or different from each other. This also applies to the definition of the number of substituents, etc.
  • substituents, etc. when a plurality of substituents, etc., are adjacent to each other (particularly, when adjacent), they may be linked to each other to form a ring, unless otherwise specified.
  • rings such as alicyclic rings, aromatic rings, and heterocyclic rings, may be further condensed to form a condensed ring.
  • the components constituting the wavelength selective absorption layer in the light absorption filter (resin A containing an acid group, dye) and the components that can be contained in the wavelength selective absorption layer (resins other than resin A, compound B that forms a hydrogen bond with the acid group contained in resin A and generates radicals by ultraviolet irradiation, and other components that may be appropriately contained, etc.) may each be contained in the wavelength selective absorption layer in one type or two or more types.
  • the components constituting the adjacent layer in the light absorption filter of the present invention may each be contained in the adjacent layer in one type or two or more types.
  • the optical filter of the present invention has a wavelength-selective absorption layer in the light-absorbing filter of the present invention that has a light-absorption loss site formed by ultraviolet irradiation.
  • the description of the light-absorbing filter of the present invention can be preferably applied to the optical filter of the present invention, except that the optical filter has this light-absorption loss site.
  • the cation is present in a delocalized state, and multiple tautomer structures exist. Therefore, in the present invention, when at least one tautomer structure of a dye falls within each general formula, the dye is considered to be a dye represented by each general formula.
  • a dye represented by a specific general formula can also be said to be a dye whose at least one tautomer structure can be represented by a specific general formula.
  • the dye represented by a general formula may have any tautomer structure as long as at least one of the tautomer structures falls within this general formula.
  • the expression of a compound is used to mean not only the compound itself, but also its salts and ions. It also means that it includes those in which a part of the structure has been changed, as long as it does not impair the effects of the present invention.
  • compounds that are not specified as substituted or unsubstituted it means that they may have any substituent, as long as it does not impair the effects of the present invention. This also applies to substituents and linking groups.
  • a numerical range expressed using “to” means a range including the numerical values before and after “to” as the lower and upper limits.
  • the composition includes not only a mixture in which the component concentrations are constant (each component is uniformly dispersed) but also a mixture in which the component concentrations vary within a range that does not impair the intended function.
  • having a main absorption wavelength band in the wavelength range of XX to YY nm means that a wavelength exhibiting maximum absorption (i.e., a maximum absorption wavelength) exists in the wavelength range of XX to YY nm.
  • the entire absorption band including this wavelength may be within the above wavelength range, or may extend outside the above wavelength range. Furthermore, if there are multiple maximum absorption wavelengths, it is sufficient that the maximum absorption wavelength exhibiting the greatest absorbance exists in the above wavelength range. In other words, the maximum absorption wavelengths other than the maximum absorption wavelength exhibiting the greatest absorbance may exist either inside or outside the above wavelength range of XX to YY nm.
  • the main absorption wavelength band of the dye is the main absorption wavelength band of the dye measured in the state of a light-absorbing filter.
  • (meth)acrylate refers to either or both of acrylate and methacrylate
  • (meth)acrylic acid refers to either or both of acrylic acid and methacrylic acid
  • (meth)acryloyl refers to either or both of acryloyl and methacryloyl.
  • the light-absorbing filter of the present invention exhibits excellent adhesion.
  • the optical filter of the present invention obtained by using a light-absorbing filter that exhibits excellent adhesion and has decolorization property which is one embodiment of the light-absorbing filter of the present invention, has light-absorbing sites and light-absorbency disappearance sites at desired positions.
  • the OLED display device, inorganic electroluminescence display device and liquid crystal display device of the present invention are equipped with the optical filter of the present invention. Furthermore, according to the manufacturing method of the present invention, it is possible to obtain the optical filter of the present invention having light absorbing sites and light absorptive non-sites at desired positions.
  • FIG. 1 is a schematic diagram showing an outline of one embodiment of a liquid crystal display device having an optical filter of the present invention.
  • FIG. 2 is a schematic cross-sectional view showing an outline of one embodiment of the light absorption filter of the present invention.
  • the light absorbing filter of the present invention is a light absorbing filter including a wavelength selective absorption layer containing a resin A containing an acid group and a dye, and an adjacent layer directly arranged (adjacent) on at least one side of the wavelength selective absorption layer, and the adjacent layer contains a resin containing a basic group.
  • the light absorbing filter of the present invention having such a configuration can show excellent interlayer adhesion.
  • the resin containing a basic group added to the adjacent layer is unevenly distributed in the adjacent layer near the interface between the wavelength selective absorption layer and the adjacent layer, and forms a hydrogen bond with the acid group contained in the resin A contained in the wavelength selective absorption layer, thereby contributing to the development of excellent adhesion.
  • Such an effect is supported by the examples described below.
  • the dye is dispersed (preferably dissolved) in the above-mentioned acid group-containing resin A, thereby making the light absorbing filter and the wavelength selective absorption layer into layers exhibiting a specific absorption spectrum derived from the dye.
  • This dispersion may be random, regular, or the like.
  • the dye may be dispersed (preferably dissolved) in the above-mentioned resin A containing an acid group and/or the resin other than the above-mentioned resin A containing an acid group.
  • the light absorbing filter of the present invention when the dye is configured to be decolorized by ultraviolet light (configuration having decolorization property), the light absorbing filter of the present invention has a property that the dye undergoes a chemical change and can be decolorized by ultraviolet light irradiation. Therefore, by performing mask exposure with ultraviolet light irradiation, it is possible to obtain the optical filter of the present invention having both a light absorbing portion having a light absorbing effect and a portion having no light absorbing property.
  • An example of the configuration of a light absorption filter capable of decolorizing a dye with ultraviolet light is a configuration in which a compound that generates radicals when irradiated with ultraviolet light is contained in the wavelength selective absorption layer of the light absorption filter of the present invention, as described in Patent Document 2.
  • a preferred example is a light absorption filter including a wavelength-selective absorption layer containing a dye, a resin A containing an acid group, and a compound B that forms a hydrogen bond with the acid group contained in the resin A and generates radicals by ultraviolet irradiation, and an adjacent layer disposed on at least one side of the wavelength-selective absorption layer, the adjacent layer containing a resin containing a basic group (hereinafter also referred to as "light absorption filter I of the present invention").
  • the "compound B that forms hydrogen bonds with the acid groups contained in the resin A and generates radicals when irradiated with ultraviolet light” forms hydrogen bonds with the acid groups contained in the resin A and is dispersed (preferably dissolved) in the resin A, generates radicals when irradiated with ultraviolet light, and the generated radicals react with nearby dyes, making the radicals more likely to react with the dye, and allowing the dye to fade and become discolored more efficiently.
  • the wavelength selective absorption layer in the light absorbing filter I of the present invention contains a dye, a resin A containing an acid group, and a compound B that forms a hydrogen bond with the acid group contained in the resin A and generates radicals by ultraviolet irradiation.
  • the light absorbing filter I of the present invention having a wavelength selective absorption layer of such a configuration can exhibit excellent adhesion, and also exhibit excellent decolorization even when irradiated with ultraviolet light in a mild environment at room temperature (meaning 10 to 30°C). The reason for this is presumed, but is thought to be as follows.
  • the wavelength-selective absorption layer in the light-absorbing filter I of the present invention it is believed that radical species having strong reducing power are generated by ultraviolet irradiation. Therefore, even when ultraviolet irradiation is performed under mild temperature conditions such as room temperature, the dye is reduced and decomposed, and the dye fades and disappears.
  • the dye contained in the wavelength-selective absorption layer in the light-absorbing filter I of the present invention contains at least one of an azo dye represented by any one of general formulas (i) to (iv) and an indoaniline dye represented by general formula (v) described below, it can be disappeared with almost no secondary absorption associated with the decomposition of the dye even when ultraviolet irradiation is performed in a mild environment of room temperature (meaning 10 to 30° C.).
  • the azo dye represented by any of the general formulas (ii) to (iv) has a structure in which an electron-donating group (amino group) is substituted at one end of the chromophore and an electron-withdrawing group (thiazole group or isothiazole group) is substituted at the other end.
  • an electron-donating group amino group
  • thiazole group or isothiazole group an electron-withdrawing group
  • the effect of stabilizing a radical by substituting both an electron-donating group and an electron-withdrawing group for the radical center is known as the "Captodative Effect" and is described, for example, in Acc. Chem. Res. Vol. 18 (1985), pp. 148-154.
  • the azo dyes represented by any one of the general formulae (ii) to (iv) also easily generate radicals due to the above-mentioned "Captodative Effect", and therefore are considered to have an excellent decolorization rate when irradiated with ultraviolet light.
  • the indoaniline dyes represented by the general formula (v) also have a structure in which an electron-donating group (amino group) is substituted at one end of the chromophore and an electron-withdrawing group (carbonyl group) is substituted at the other end, and due to the above-mentioned "Captodative Effect", an excellent decolorization rate is obtained even when irradiated with ultraviolet light under mild temperature conditions such as room temperature.
  • the azo dyes represented by any one of the general formulae (ii) to (iv) and the indoaniline dyes represented by the general formula (v) themselves are considered to have excellent decolorization properties because they hardly cause secondary absorption associated with the decomposition of the dye.
  • a benzylidene dye or a cinnamylidene dye represented by the general formula (V) described in Patent Document 2 is described as a dye having a main absorption wavelength band in the wavelength range of approximately 400 to 500 nm.
  • the decolorization rate is as low as 84%, as described in Comparative Example No. c202 in the Reference Example described later, and the decolorization property at room temperature is poor.
  • the light absorption filter of the present invention has a main absorption wavelength band in the wavelength range of approximately 400 to 500 nm by containing an azo dye represented by the general formula (i) described later instead of the benzylidene dye or cinnamylidene dye represented by the general formula (V) described in Patent Document 2, and can exhibit excellent decolorization property even when irradiated with ultraviolet light at room temperature (meaning 10 to 30° C.), which is a mild environment.
  • the light-absorbing filter of the present invention contains an azo dye represented by any one of general formulas (ii) to (iv) described below or an indoaniline dye represented by general formula (v), and thus has a main absorption wavelength band in the wavelength region of approximately 450 to 700 nm, and can exhibit excellent decolorization properties comparable to those of a light-absorbing filter containing a squaraine dye represented by general formula (1) described in Patent Document 2, even when irradiated with ultraviolet light in a mild environment, that is, room temperature (meaning 10 to 30° C.).
  • the wavelength-selective absorption layer and adjacent layers in the light absorption filter of the present invention will be described in order.
  • the wavelength selective absorption layer in the light absorption filter of the present invention contains a resin A containing an acid group and a dye.
  • the dye contained in the wavelength selective absorption layer is not particularly limited, and for example, a dye having a main absorption wavelength band in the wavelength range of 400 to 700 nm can be used.
  • the dye contained in the wavelength selective absorption layer preferably contains at least one kind of an azo dye represented by any one of general formulas (i) to (iv) below and an indoaniline dye represented by general formula (v) below, and more preferably contains at least one kind of an azo dye represented by general formula (i) below and an indoaniline dye represented by general formula (v) below.
  • the azo dye represented by the general formula (i) described below is a dye having a main absorption wavelength band in a wavelength range of about 400 to 500 nm
  • the azo dye represented by any of the general formulas (ii) to (iv) described below is a dye having a main absorption wavelength band in a wavelength range of about 450 to 600 nm
  • the indoaniline dye represented by the general formula (v) described below is a dye having a main absorption wavelength band in a wavelength range of about 580 to 700 nm.
  • Each of the azo dye represented by the following general formula (i), the azo dye represented by the following general formula (ii), the azo dye represented by the following general formula (iii), the azo dye represented by the following general formula (iv), and the indoaniline dye represented by the following general formula (v), which can be contained in the wavelength selective absorption layer, may be one type or two or more types.
  • the wavelength selective absorption layer may contain a dye other than the above dyes.
  • R 17 and R 18 each independently represent a hydrogen atom or a monovalent substituent.
  • R 19 represents a hydrogen atom, an aliphatic group, an aryl group, a heterocyclic group, a carbamoyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an acyl group, an alkylsulfonyl group, an arylsulfonyl group, or a sulfamoyl group.
  • Q represents a residue of a diazo component.
  • R 17 to R 19 and Q do not have a squaraine structure.
  • the above-mentioned squaraine structure means the structure of a squaraine dye.
  • a squaraine dye is a dye having a structure in which a skeleton derived from squaric acid is located at the center of a ⁇ -conjugated system.
  • a squaraine dye represented by the general formula (1) described in Patent Document 2 can be mentioned.
  • Examples of the monovalent substituent which may be taken as R 17 and R 18 include a halogen atom, an aliphatic group, an aryl group, a heterocyclic group, a cyano group, a carboxy group, a carbamoyl group, an aliphatic oxycarbonyl group, an aryloxycarbonyl group, an acyl group, a hydroxy group, an aliphatic oxy group, an aryloxy group, an acyloxy group, a carbamoyloxy group, a heterocyclic oxy group, an amino group (-NH 2 ), an aliphatic amino group, an arylamino group, a heterocyclic amino group, an acylamino group, a carbamoylamino group, a sulfamoylamino group, an aliphatic oxycarbonylamino group, an aryloxycarbonylamino group, an aliphatic sulfonylamino group, an
  • an aliphatic group, an aryl group, a heterocyclic group, a cyano group, a carbamoyl group, an aliphatic oxycarbonyl group, an aryloxycarbonyl group, an acyl group, an aliphatic oxy group, an aryloxy group, an aliphatic amino group, or an arylamino group is preferred.
  • the substituents which can be adopted as these R 17 and R 18 may be further substituted.
  • the aliphatic groups which can be taken as R 17 to R 19 may further have a monovalent substituent, may be saturated or unsaturated, and may be cyclic. Specific examples include alkyl groups, substituted alkyl groups, alkenyl groups, substituted alkenyl groups, alkynyl groups, substituted alkynyl groups, aralkyl groups, and substituted aralkyl groups.
  • the total number of carbon atoms in the aliphatic group is preferably 1 to 30, and more preferably 1 to 16.
  • the aliphatic group examples include a methyl group, an ethyl group, a butyl group, an isopropyl group, a t-butyl group, a hydroxyethyl group, a methoxyethyl group, a cyanoethyl group, a trifluoromethyl group, a 3-sulfopropyl group, a 4-sulfobutyl group, a 2-(2-hydroxyethoxy)ethyl group, a 2-(2-(acetyloxy)ethoxy)ethyl group, a cyclohexyl group, a benzyl group, a 2-phenethyl group, a vinyl group, and an allyl group.
  • examples of the monovalent substituent that may be possessed include the monovalent substituents that may be taken as R 17 and R 18 , and the same applies to the following explanation of the monovalent substituent that may be possessed.
  • examples of the monovalent substituent that may be possessed are preferably an alkoxy group, an acyloxy group, a hydroxy group, etc.
  • these substituents may further have a substituent, and examples of the preferred substituents include an alkoxy group, an acyloxy group, a hydroxy group, etc.
  • the aryl group which can be taken as R 17 to R 19 may further have a monovalent substituent, and is preferably an aryl group having a total carbon number of 6 to 30, more preferably 6 to 16.
  • the heterocyclic group which can be taken as R 17 to R 19 may be a saturated or unsaturated aliphatic ring group, or may be an aromatic ring group, and is preferably an aromatic heterocyclic group.
  • ring-constituting atoms constituting the heterocyclic group include those containing at least one heteroatom such as a nitrogen atom, a sulfur atom, or an oxygen atom, and may further have a monovalent substituent.
  • the heterocyclic group is preferably a heterocyclic group having a total of 1 to 30 carbon atoms, and more preferably a heterocyclic group having 1 to 15 carbon atoms. Specific examples include a 2-pyridyl group, a 2-thienyl group, a 2-thiazolyl group, a 2-benzothiazolyl group, a 2-benzoxazolyl group, and a 2-furyl group.
  • the carbamoyl groups which can be taken as R 17 to R 19 include unsubstituted carbamoyl groups (—CONH 2 ) as well as carbamoyl groups substituted with an aliphatic group, an aryl group, or the like.
  • the carbamoyl group which can be represented by R 17 to R 19 may further have a monovalent substituent and is preferably a carbamoyl group having a total of 1 to 30 carbon atoms, more preferably a carbamoyl group having a total of 1 to 16 carbon atoms. Specific examples include a methylcarbamoyl group, a dimethylcarbamoyl group, a phenylcarbamoyl group, and an N-methyl-N-phenylcarbamoyl group.
  • the aliphatic oxycarbonyl group which can be represented by R 17 and R 18 may further have a monovalent substituent, may be saturated or unsaturated, may be cyclic, and is preferably an aliphatic oxycarbonyl group having a total of 2 to 30 carbon atoms, more preferably an aliphatic oxycarbonyl group having a total of 2 to 16 carbon atoms. Specific examples include a methoxycarbonyl group, an ethoxycarbonyl group, and a 2-methoxyethoxycarbonyl group.
  • the alkoxycarbonyl group which can be taken as R 19 may further have a monovalent substituent, may be saturated or unsaturated, may be cyclic, and is preferably an alkoxycarbonyl group having a total of 2 to 30 carbon atoms, more preferably an alkoxycarbonyl group having a total of 2 to 16 carbon atoms. Specific examples include a methoxycarbonyl group, an ethoxycarbonyl group, and a 2-methoxyethoxycarbonyl group.
  • the aryloxycarbonyl group which can be represented by R 17 to R 19 may further have a monovalent substituent, and is preferably an aryloxycarbonyl group having a total of 7 to 30 carbon atoms, more preferably an aryloxycarbonyl group having a total of 7 to 16 carbon atoms.
  • Specific examples include a phenoxycarbonyl group, a 4-methylphenoxycarbonyl group, and a 3-chlorophenoxycarbonyl group.
  • the acyl groups which can be taken as R 17 to R 19 include an aliphatic carbonyl group, an arylcarbonyl group, and a heterocyclic carbonyl group, and preferably have a total carbon number of 1 to 30, more preferably have a total carbon number of 1 to 16. Specific examples include an acetyl group, a methoxyacetyl group, a thienoyl group, and a benzoyl group.
  • the aliphatic sulfonyl group which can be represented by R 17 and R 18 may further have a monovalent substituent, may be saturated or unsaturated, may be cyclic, and preferably has a total of 1 to 30 carbon atoms, more preferably has a total of 1 to 16 carbon atoms. Specific examples include a methanesulfonyl group, a methoxymethanesulfonyl group, and an ethoxyethanesulfonyl group.
  • the alkylsulfonyl group which can be taken as R 19 may further have a monovalent substituent, may be saturated or unsaturated, may be cyclic, and preferably has a total of 1 to 30 carbon atoms, more preferably has a total of 1 to 16 carbon atoms.
  • Specific examples include a methanesulfonyl group, a methoxymethanesulfonyl group, and an ethoxyethanesulfonyl group.
  • the arylsulfonyl group which can be represented by R 17 to R 19 may further have a monovalent substituent and preferably has a total of 6 to 30 carbon atoms, more preferably has a total of 6 to 18 carbon atoms.
  • Specific examples include a benzenesulfonyl group and a toluenesulfonyl group.
  • Sulfamoyl groups which can be taken as R 17 to R 19 include unsubstituted sulfamoyl groups (—SO 2 NH 2 ) as well as sulfamoyl groups substituted with an aliphatic group, an aryl group, or the like.
  • the sulfamoyl group which can be represented by R 17 to R 19 may further have a monovalent substituent and preferably has a total of 0 to 30 carbon atoms, more preferably has a total of 0 to 16 carbon atoms. Specific examples include an unsubstituted sulfamoyl group, a dimethylsulfamoyl group, and a di-(2-hydroxyethyl)sulfamoyl group.
  • the imido group which can be taken as R 17 and R 18 may further have a monovalent substituent, and is preferably a 5- or 6-membered ring imido group.
  • the imido group preferably has a total carbon number of 4 to 30, more preferably 4 to 20. Specific examples include a succinimide group and a phthalimide group.
  • aliphatic group in the aliphatic oxy group aliphatic amino group, aliphatic oxycarbonylamino group, aliphatic sulfonylamino group, and aliphatic thio group which can be taken as R 17 and R 18
  • the descriptions of the aliphatic groups which can be taken as R 17 to R 19 can be applied.
  • the aryl group in the aryloxy group arylamino group, aryloxycarbonylamino group, arylsulfonylamino group and arylthio group which can be taken as R 17 and R 18
  • the descriptions of the aryl group which can be taken as R 17 to R 19 can be applied.
  • the descriptions of the acyl group which can be taken as R 17 to R 19 can be applied.
  • the carbamoyl group in the carbamoyloxy group and carbamoylamino group which can be taken as R 17 and R 18 the descriptions of the carbamoyl groups which can be taken as R 17 to R 19 can be applied.
  • the heterocyclic group in the heterocyclic oxy group heterocyclic amino group and heterocyclic thio group which can be taken as R 17 and R 18
  • the descriptions of the heterocyclic groups which can be taken as R 17 to R 19 can be applied.
  • the sulfamoyl group in the sulfamoylamino group which can be taken as R 17 and R 18 the descriptions of the sulfamoyl groups which can be taken as R 17 to R 19 can be applied.
  • the diazo component residue represented by Q means the residue "Q” of the diazo component "Q-NH 2 ".
  • the azo dye represented by the above general formula (i) is obtained by a diazo coupling reaction using the diazonium ion "Q-N + ⁇ N" obtained from the diazo component "Q-NH 2 ".
  • Q is an aryl group or an aromatic heterocyclic group.
  • the aromatic hydrocarbon ring constituting the aryl group that can be taken as Q may be a monocyclic ring or a condensed ring, and is preferably a monocyclic ring.
  • An aryl group having a total carbon number of 6 to 30 is preferable, and an aryl group having a total carbon number of 6 to 16 is more preferable. Specifically, a phenyl group is preferable.
  • the aryl group that can be taken as Q may have a substituent, and preferred examples of the substituent that may be had include a sulfamoyl group (preferably an alkylsulfamoyl group or a dialkylsulfamoyl group), a sulfonyl group (preferably an alkylsulfonyl group), and a cyano group.
  • the aromatic heterocyclic group that can be taken as Q is preferably an aromatic ring group containing at least one heteroatom such as a nitrogen atom, a sulfur atom, or an oxygen atom as a ring-constituting atom constituting the heterocyclic group, and is preferably constituted by a 5- to 6-membered ring.
  • the total number of carbon atoms in the aromatic heterocyclic group is preferably 1 to 25, more preferably 1 to 15.
  • the aromatic heterocycle constituting the aromatic heterocyclic group may be a monocycle or a condensed ring, and is preferably a monocycle.
  • aromatic heterocyclic group examples include a pyrazole group, a 1,2,4-triazole group, an isothiazole group, a benzoisothiazole group, a thiazole group, a benzothiazole group, an oxazole group, and a 1,2,4-thiadiazole group.
  • Examples of the azo dye represented by the above general formula (i) include the following exemplary compounds (B-12) to (B-16), (B-18), and (B-19). However, the present invention is not limited to these.
  • R 21 to R 24 , R 26 and R 27 each represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfo group, -OR 108 , -SR 109 , -NR 110 R 111 , -S( ⁇ O) 2 NR 112 R 113 , -C( ⁇ O)NR 114 R 115 , -NHC( ⁇ O)R 116 , -C( ⁇ O)OR 117 , -O(CH 2 CH 2 O) n R 118 , -O(CH 2 CH 2 S) n R 119 , -S(CH 2 CH 2 O) n R 120 and -S(CH 2 CH 2 S) n R 121 .
  • R 108 to R 121 each represent a hydrogen atom, a non-cyclic hydrocarbon group, a monocyclic hydrocarbon group, a condensed polycyclic hydrocarbon group or a heterocyclic group, and n is a positive integer.
  • the acyclic hydrocarbon group, the monocyclic hydrocarbon group, the condensed polycyclic hydrocarbon group and the heterocyclic group include a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfo group, -OR 108 , -SR 109 , -NR 110 R 111 , -S( ⁇ O) 2 NR 112 R 113 , -C( ⁇ O)NR 114 R 115 , -NHC( ⁇ O)R 116 , -C( ⁇ O)OR 117 , -O(CH 2 CH 2 O) n R 118 , -O(CH 2 CH 2 S) n R 119 , -S(CH 2 CH 2 O) n R 120 and -S(CH 2 CH 2 S) n R 121
  • the aryl group may have one or more of acyclic hydrocarbon groups, monocyclic hydrocarbon groups, condensed polycyclic hydrocarbon groups, and hetero
  • the acyclic hydrocarbon group which may be represented by R 21 to R 24 , R 26 , R 27 and R 108 to R 121 means an acyclic alkyl group in which one hydrogen atom has been removed from an acyclic alkane.
  • the acyclic alkyl group may have a ring structure as a substituent.
  • the number of carbon atoms in the acyclic alkyl group is preferably 1 to 30, more preferably 1 to 20, still more preferably 1 to 12, particularly preferably 1 to 8, and of these, 1 to 6 is preferred.
  • the monocyclic hydrocarbon group which may be taken as R 21 to R 24 , R 26 , R 27 and R to R 121 means a monocyclic cycloalkyl group, a monocyclic cycloalkenyl group, a monocyclic cycloalkynyl group or a monocyclic aryl group which is a group in which one hydrogen atom has been removed from a monocyclic aliphatic hydrocarbon ring (which may be any of a monocyclic cycloalkane, a monocyclic cycloalkene and a monocyclic cycloalkyne) or a monocyclic aromatic hydrocarbon ring.
  • the number of carbon atoms in the monocyclic cycloalkyl group, monocyclic cycloalkenyl group, and monocyclic cycloalkynyl group is not particularly limited as long as it is structurally possible, but is more preferably 3 to 30, more preferably 3 to 20, and even more preferably 3 to 16.
  • the number of carbon atoms in the monocyclic aryl group is more preferably 6 to 30, more preferably 6 to 20, and even more preferably 6 to 16.
  • the fused polycyclic hydrocarbon group which may be taken as R 21 to R 24 , R 26 , R 27 and R to R 121 means a fused polycyclic cycloalkyl group, a fused polycyclic cycloalkenyl group, a fused polycyclic cycloalkynyl group or a fused polycyclic aryl group which is a group in which one hydrogen atom has been removed from a fused polycyclic aliphatic hydrocarbon ring (which may be any of a fused polycyclic cycloalkane, a fused polycyclic cycloalkene and a fused polycyclic cycloalkyne) or a fused polycyclic aromatic hydrocarbon ring.
  • the number of carbon atoms in the fused polycyclic cycloalkyl group, the fused polycyclic cycloalkenyl group, and the fused polycyclic cycloalkynyl group is not particularly limited as long as it is structurally possible, but is more preferably 8 to 30, and more preferably 8 to 20.
  • the number of carbon atoms in the fused polycyclic aryl group is more preferably 12 to 30, and more preferably 12 to 20.
  • the heterocyclic groups which can be taken as R 21 to R 24 , R 26 , R 27 and R 108 to R 121 the description of the heterocyclic groups which can be taken as R 17 to R 19 in the above general formula (i) can be applied.
  • n is preferably an integer of 1 to 12, more preferably an integer of 1 to 6, and even more preferably an integer of 1 to 3.
  • R 21 is preferably a cyano group, a nitro group, -OR 108 , an acyclic hydrocarbon group (preferably an acyclic alkyl group or an acyclic alkenyl group) or a heterocyclic group, more preferably a cyano group or a nitro group, or an acyclic alkyl group substituted with a halogen atom (preferably an alkyl group substituted with a fluorine atom), and further preferably a cyano group.
  • an acyclic hydrocarbon group preferably an acyclic alkyl group or an acyclic alkenyl group
  • a heterocyclic group more preferably a cyano group or a nitro group
  • a halogen atom preferably an alkyl group substituted with a fluorine atom
  • R 22 is preferably a hydrogen atom, a cyano group, an acyclic hydrocarbon group (preferably an acyclic alkyl group) or a monocyclic hydrocarbon group, more preferably a hydrogen atom, an alkyl group or an aryl group, and even more preferably an alkyl group or an aryl group. At least one of R 21 and R 22 is preferably a cyano group, a nitro group, or a non-cyclic alkyl group substituted with a halogen atom, a cyano group, or a nitro group.
  • R 23 is preferably a hydrogen atom, -OR 108 , -SR 109 , -NR 110 R 111 , -C( ⁇ O)NR 114 R 115 , -NHC( ⁇ O)R 116 , -O(CH 2 CH 2 O) n R 118 , -O(CH 2 CH 2 S) n R 119 , -S(CH 2 CH 2 O) n R 120 , -S(CH 2 CH 2 S) n R 121 or a non-cyclic hydrocarbon group (preferably a non-cyclic alkyl group), and a hydrogen atom, -OR 108 , -SR 109 , -NR 110 R 111 , -NHC( ⁇ O)R 116 or a non-cyclic alkyl group is more preferable, and --NHC(.dbd.O)R 116 is further preferable.
  • R 108 to R 111 , R 114 to R 116 and R 118 to R 121 are preferably a non-cyclic alkyl group.
  • R 24 and R 27 are preferably a hydrogen atom.
  • R 26 is preferably a hydrogen atom, -OR 108 , -SR 109 , -NR 110 R 111 , -NHC( ⁇ O)R 116 , -O(CH 2 CH 2 O) n R 118 , -O(CH 2 CH 2 S) n R 119 , -S(CH 2 CH 2 O) n R 120 , -S(CH 2 CH 2 S) n R 121 or a non-cyclic hydrocarbon group (preferably a non-cyclic alkyl group), more preferably a hydrogen atom, -OR 108 or -SR 109 , and even more preferably a hydrogen atom.
  • R 108 to R 111 , R 116 and R 118 to R 121 are preferably a non-cyclic alkyl group.
  • R 110 is preferably an acyclic alkyl group
  • R 111 is preferably an acyclic alkyl group, more preferably an unsubstituted acyclic alkyl group, or an acyclic alkyl group having -OR 108 , a monocyclic hydrocarbon group or a condensed polycyclic hydrocarbon group as a substituent, wherein R 108 is preferably a hydrogen atom or an acyclic alkyl group.
  • dye represented by formula (ii) include the compounds used in the Examples section below, as well as the compounds described in paragraphs [0023] to [0034] of JP-A-5-257180, and the compounds described in paragraphs [0050] and [0052] of JP-A-2013-129712, compound D-18 described in paragraph [0055], and the compound described in paragraph [0056].
  • the present invention is not limited to these.
  • R 31 represents a hydrogen atom, an alkyl group, an alkoxy group, a cyano group, a carbonyl group (preferably an alkyloxycarbonyl group or an aryloxycarbonyl group), an aromatic group or a heterocyclic group.
  • R 32 represents a hydrogen atom, an alkyl group, an alkoxy group, a cyano group, a nitro group, a carbonyl group (preferably an alkyloxycarbonyl group or an aryloxycarbonyl group), an aromatic group or a heterocyclic group.
  • R 34 and R 35 each independently represent a hydrogen atom, an alkyl group or an aromatic group.
  • R 37 represents a hydrogen atom, an alkyl group, an alkoxy group, a cyano group, a carbonyl group (preferably an alkyloxycarbonyl group or an aryloxycarbonyl group), an acylamino group or an aromatic group.
  • R 34 and R 35 may be bonded to each other to form a ring.
  • R 1 and R 2 in relation to the general formula (1) described in JP-A-2013-129712 can be directly applied to R 31 and R 32 , respectively, and the description of R 4 , R 5 and R 7 in relation to the general formula (3) described in JP-A-2013-129712 can be directly applied to R 34 , R 35 and R 37 , respectively.
  • R 37 can be the following acylamino group in addition to the hydrogen atom, alkyl group, alkoxy group, cyano group, carbonyl group, and aromatic group that R 7 in the general formula (3) described in JP2013-129712A can be.
  • the acylamino group which can be represented by R 37 preferably has 1 to 12 carbon atoms, and more preferably has 1 to 6 carbon atoms.
  • the alkyl group which can be represented by R 31 , R 32 and R 37 preferably has 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms.
  • the alkoxy group which can be represented by R 31 , R 32 and R 37 preferably has 1 to 20 carbon atoms, more preferably 1 to 12 carbon atoms, and particularly preferably 1 to 6 carbon atoms.
  • the alkyloxycarbonyl group which can be represented by R 31 , R 32 and R 37 preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, further preferably 2 to 12 carbon atoms, and particularly preferably 2 to 7 carbon atoms.
  • the alkyl group which can be represented by R 34 and R 35 preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and even more preferably 1 to 12 carbon atoms.
  • R 31 is preferably an alkyl group or an aryl group, more preferably an alkyl group.
  • R 32 is preferably an alkyl group or a cyano group, more preferably a cyano group.
  • R 34 and R 35 are preferably a hydrogen atom or an alkyl group, more preferably an alkyl group.
  • R 37 is preferably a hydrogen atom, an alkyl group, an acylamino group or an aromatic group, more preferably a hydrogen atom or an alkyl group, and even more preferably an alkyl group.
  • R 41 to R 44 , R 46 and R 47 each represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfo group, -OR 208 , -SR 209 , -NR 210 R 211 , -S( ⁇ O) 2 NR 212 R 213 , -C( ⁇ O)NR 214 R 215 , -NHC( ⁇ O)R 216 , -C( ⁇ O)OR 217 , -O(CH 2 CH 2 O) n R 218 , -O(CH 2 CH 2 S) n R 219 , -S(CH 2 CH 2 O) n R 220 and -S(CH 2 CH 2 S) n R 221 .
  • R 208 to R 221 each represent a hydrogen atom, a non-cyclic hydrocarbon group, a monocyclic hydrocarbon group, a condensed polycyclic hydrocarbon group or a heterocyclic group, and n is a positive integer.
  • the acyclic hydrocarbon group, the monocyclic hydrocarbon group, the condensed polycyclic hydrocarbon group and the heterocyclic group include a halogen atom, a cyano group, a nitro group, a carboxy group, a sulfo group, -OR 208 , -SR 209 , -NR 210 R 211 , -S( ⁇ O) 2 NR 212 R 213 , -C( ⁇ O)NR 214 R 215 , -NHC( ⁇ O)R 216 , -C( ⁇ O)OR 217 , -O(CH 2 CH 2 O) n R 218 , -O(CH 2 CH 2 S) n R 219 , -S(CH 2 CH 2 O) n R 220 and -S(CH 2 CH 2 S) n R 221
  • the aryl group may have one or more of acyclic hydrocarbon groups, monocyclic hydrocarbon groups, condensed polycyclic hydrocarbon groups,
  • R 208 to R 211 , R 216 and R 218 to R 221 are preferably acyclic alkyl groups.
  • R 210 is preferably an acyclic alkyl group
  • R 211 is preferably an acyclic alkyl group, more preferably an unsubstituted acyclic alkyl group (including an acyclic alkyl group substituted with an acyclic alkyl group), or -OR 208 , an acyclic alkyl group having a monocyclic hydrocarbon group or a condensed polycyclic hydrocarbon group as a substituent.
  • R 208 is preferably a hydrogen atom or an acyclic alkyl group.
  • R 44 and/or R 46 in general formula (iv) may be bonded to R 210 and/or R 211 in -NR 210 R 211 located at the ortho position relative to R 44 and R 46 on the benzene ring to form a ring.
  • the ring that may be formed is preferably a 5- or 6-membered ring, and may be saturated or unsaturated, and is preferably a saturated 6-membered ring.
  • the ring that may be formed may further have a substituent, and preferably has, for example, an alkyl group.
  • the ring is preferably formed by bonding R 46 to R 211 in --NR 210 R 211 located at the ortho position relative to R 44 and R 46 on the benzene ring to form a saturated 6-membered ring.
  • Q1 represents a group of atoms necessary to form a 5- to 7-membered nitrogen-containing heterocycle together with the carbon atom to which it is bonded, including at least one nitrogen atom.
  • R 51 represents an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an aminocarbonyl group (carbamoyl group) or a sulfonyl group
  • R 52 represents a hydrogen atom or an alkyl group
  • R 53 to R 57 represent a hydrogen atom, an alkyl group, an alkoxy group, an acylamino group, an alkylsulfonylamino group or a halogen atom
  • R 58 and R 59 represent a hydrogen atom, an alkyl group or an aryl group.
  • R51 and R53 , R54 and R55 and/or R55 and R59 , or R58 and R59 may be bonded to each other to form a ring. That is, it means that R51 and R53 may be bonded to each other to form a ring, R54 and R55 and/or R55 and R59 may be bonded to each other to form a ring, or R58 and R59 may be bonded to each other to form a ring.
  • R 1 to R 6 , R 8 , R 9 and Q 1 in general formula (I) described in JP-A-2-92686 can be directly applied to R 51 to R 56 , R 58 , R 59 and Q 1 , respectively, unless otherwise specified.
  • R 53 to R 56 can be the following acylamino group and alkylsulfonylamino group in addition to the hydrogen atom, alkyl group, alkoxy group and halogen atom which R 3 to R 6 in the general formula (I) described in JP-A-2-92686 can be.
  • the acylamino group which can be represented by R 53 to R 57 preferably has 1 to 12 carbon atoms, and more preferably has 1 to 6 carbon atoms.
  • the alkylsulfonylamino group which can be represented by R 53 to R 57 preferably has 1 to 12 carbon atoms, and more preferably has 1 to 6 carbon atoms.
  • R 16 represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group, and a hydrogen atom is preferred.
  • the definition and preferred range of each substituent of R 16 are the same as those described in JP-A-2-92686 regarding R 16 in the general formula (I).
  • R 51 is preferably an acyl group having 2 to 7 carbon atoms or an alkoxycarbonyl group having 2 to 7 carbon atoms.
  • R 52 is preferably a hydrogen atom, and R 53 to R 56 are preferably hydrogen atoms.
  • R 57 is preferably an alkoxy group, an acylamino group or an alkylsulfonylamino group, more preferably an alkoxy group or an acylamino group.
  • R 58 and R 59 are preferably an alkyl group having 1 to 6 carbon atoms.
  • indoaniline dye represented by the above general formula (v) is preferably represented by the following general formula (v-a):
  • R 51 , R 53 , R 57 to R 59 and Q 2 have the same meanings as R 51 , R 53 , R 57 to R 59 and Q 2 in general formula (v) above.
  • Q2 is preferably -CR 11 R 12 CR 13 R 14 -, -CR 11 R 12 - or -NR 11 -, and more preferably -CR 11 R 12 CR 13 R 14 -.
  • R 11 to R 14 each represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and it is preferred that R 11 and R 12 are hydrogen atoms and R 13 and R 14 are alkyl groups having 1 to 4 carbon atoms.
  • --CR 11 R 12 CR 13 R 14 -- is bonded to >C ⁇ O on the side of the carbon atom to which R 11 and R 12 are bonded.
  • the total content of the dyes in the wavelength selective absorption layer is preferably 0.10% by mass or more, more preferably 0.15% by mass or more, even more preferably 0.20% by mass or more, particularly preferably 0.25% by mass or more, and particularly preferably 0.30% by mass or more.
  • the total content of the dyes in the wavelength selective absorption layer is equal to or more than the above-mentioned preferable lower limit, a good antireflection effect can be obtained.
  • the total content of the dyes in the wavelength selective absorption layer is usually 50% by mass or less, preferably 40% by mass or less, more preferably 30% by mass or less, even more preferably 15% by mass or less, and particularly preferably 10% by mass or less.
  • the total content of the dyes in the wavelength selective absorption layer is preferably 0.10 to 50 mass%, more preferably 0.15 to 40 mass%, even more preferably 0.20 to 30 mass%, particularly preferably 0.25 to 15 mass%, and especially preferably 0.30 to 10 mass%.
  • the content of the azo dye represented by the general formula (i) in the wavelength selective absorption layer is preferably 0.01 to 30% by mass, more preferably 0.1 to 10% by mass.
  • the content of each of the azo dye represented by the general formula (ii), the azo dye represented by the general formula (iii), the azo dye represented by the general formula (iv), and the indoaniline dye represented by the general formula (v) in the wavelength selective absorption layer is preferably 0.01 to 30% by mass, more preferably 0.1 to 10% by mass, similar to the content of the azo dye represented by the general formula (i).
  • all of the dyes may be composed of at least one of the azo dye represented by any one of the general formulas (i) to (iv) and the indoaniline dye represented by the general formula (v).
  • the resin (hereinafter also referred to as "matrix resin") contained in the wavelength selective absorption layer is not particularly limited as long as it can disperse (preferably dissolve) the above-mentioned dye and has the desired light transmittance (in the visible region of wavelengths of 400 to 800 nm, the light transmittance is preferably 80% or more).
  • the resin contained in the wavelength selective absorption layer may be the resin A containing an acid group described below, or may contain other resins in addition to the resin A containing an acid group described below.
  • the resin contained in the wavelength selective absorption layer is not particularly limited as long as it can form a hydrogen bond with the acid group contained in the resin A and can exhibit the decolorization action of the dye by the radicals generated from the compound B which generates radicals upon irradiation with ultraviolet light.
  • Various polymers can be used as the polymer constituting the resin. From the viewpoint of the molecular weight of the resin being unlikely to decrease due to ultraviolet irradiation, a polymer having an aromatic ring or an alicyclic structure in a side chain is preferred, and a (meth)acrylic polymer containing a structural unit having an aromatic ring or an alicyclic structure is more preferred. Among them, from the viewpoint of the decolorization rate being more improved and the heat resistance and light resistance being more improved, a (meth)acrylic polymer containing a structural unit having an alicyclic structure is even more preferred.
  • the (meth)acrylic polymer refers to a polymer containing at least one of a structural unit derived from (meth)acrylic acid and a structural unit derived from a (meth)acrylic acid ester.
  • the structural unit derived from (meth)acrylic acid becomes a structural unit having a carboxy group as an acid group contained in the resin A described below, and corresponds to the carboxy group-containing polymer constituting the resin A described below.
  • the term "main chain” refers to the relatively longest bonding chain in the molecule of a polymer compound
  • side chain refers to an atomic group branching off from the main chain.
  • Monomers which lead to structural units having an aromatic ring include benzyl acrylate, benzyl methacrylate, naphthyl acrylate, naphthyl methacrylate, naphthyl methyl acrylate, and naphthyl methyl methacrylate.
  • the content of structural units having an aromatic ring is preferably 5 to 100% by mass, more preferably 10 to 100% by mass, and even more preferably 20 to 100% by mass, based on the total mass of the polymer.
  • Monomers that lead to structural units having an alicyclic structure include dicyclopentanyl (meth)acrylate, cyclohexyl (meth)acrylate, and isobornyl (meth)acrylate.
  • the content of the structural unit having an alicyclic structure is preferably 1 to 90 mass %, more preferably 5 to 90 mass %, and even more preferably 5 to 80 mass %, relative to the total mass of the polymer.
  • the polymer constituting the resin may contain a structural unit having an alkyl group having 1 to 14 carbon atoms from the viewpoint of adjusting the glass transition temperature, etc.
  • structural units having an alkyl group having 1 to 14 carbon atoms include structural units derived from alkyl (meth)acrylates such as methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, t-butyl (meth)acrylate, sec-butyl (meth)acrylate, pentyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, 2-ethylbutyl (meth)acrylate, n-octyl (meth)acrylate, isooctyl (meth)acrylate, isononyl (meth)acrylate, lauryl (meth)acrylate, and
  • structural units having an alkyl group having 1 to 14 carbon atoms may be used alone, or two or more types may be used in combination.
  • the content of structural units having an alkyl group with 1 to 14 carbon atoms is preferably 0 to 95% by mass relative to the total mass of the polymers that make up the resin.
  • the weight average molecular weight (Mw) of the polymer constituting the resin is preferably 10,000 or more, more preferably 10,000 to 200,000, and even more preferably 15,000 to 150,000.
  • the wavelength selective absorption layer contains a resin A containing an acid group (in the present invention, also simply referred to as "resin A").
  • the acid group contained in resin A is preferably a proton dissociative group having a pKa of 12 or less.
  • the resin A containing an acid group means that the polymer constituting the resin A contains an acid group.
  • the lower limit of the weight average molecular weight of the polymer constituting resin A is 5,000 or more, and from the viewpoint of the physical properties of the optical filter, it is preferably 10,000 or more, and more preferably 15,000 or more.
  • the upper limit is not particularly limited, but from the viewpoint of solubility in a solvent, it is preferably 500,000 or less, more preferably 200,000 or less, and even more preferably 150,000 or less. That is, 5,000 to 500,000 is practical and preferable, 10,000 to 200,000 is more preferable, and 15,000 to 150,000 is more preferable.
  • the weight average molecular weight of the polymer can be measured as a polystyrene-equivalent molecular weight by gel permeation chromatography (GPC).
  • a GPC apparatus HLC-8220 (product name, manufactured by Tosoh Corporation) is used, tetrahydrofuran is used as an eluent, and G3000HXL+G2000HXL columns (both product names, manufactured by Tosoh Corporation) are used, and detection can be performed by RI (differential refractive index) at 23° C. and a flow rate of 1 mL/min.
  • RI differential refractive index
  • resin A may or may not be anionized in the light absorbing filter, and in the present invention, both anionized and non-anionized acid groups are referred to as acid groups.
  • resin A may or may not be anionized in the light absorbing filter.
  • the polymer constituting resin A is preferably a polymer having a carboxy group, i.e., a carboxy group-containing polymer, in view of its excellent film-forming properties for the light absorbing filter.
  • carboxy groups (-COOH) of the carboxy group-containing polymer may be anionized or not in the light-absorbing filter, and both anionized carboxy groups (-COO - ) and non-anionized carboxy groups are referred to as carboxy groups.
  • carboxy groups both anionized carboxy groups (-COO - ) and non-anionized carboxy groups are referred to as carboxy groups.
  • the carboxy group-containing polymer may be either anionized or non-anionized in the light absorbing filter, and both anionized and non-anionized carboxy group-containing polymers are referred to as the carboxy group-containing polymer.
  • the content of the resin A in the wavelength selective absorption layer is preferably 50% by mass or more and less than 100% by mass, more preferably 60% by mass or more and less than 100% by mass, and even more preferably 65% by mass or more and less than 100% by mass.
  • the upper limit is also preferably 99% by mass or less, more preferably 97% by mass or less, even more preferably 95% by mass or less, and particularly preferably 90% by mass or less.
  • Resin A may be used alone or in combination of two or more kinds.
  • the carboxyl group-containing polymer may further have an acid group other than the carboxyl group.
  • the acid group other than the carboxyl group include a phenolic hydroxyl group, a phosphoric acid group, and a sulfonic acid group.
  • the carboxy group-containing polymer is a copolymer
  • the polymer structure may be a random polymer or a regular polymer such as a block polymer.
  • the carboxy group-containing polymer preferably has a structural unit having a carboxy group.
  • the structural unit having a carboxy group include structural units derived from (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid, or fumaric acid. Among these, structural units derived from (meth)acrylic acid are preferred because of their excellent decolorization properties.
  • the content of the structural unit having a carboxy group is preferably 1 to 100 mol%, more preferably 10 to 90 mol%, even more preferably 30 to 90 mol%, particularly preferably 45 to 80 mol%, and especially preferably 45 to 75 mol%, when the total of all structural units of the carboxy group-containing polymer is 100 mol%.
  • the structural unit having a carboxy group may be used alone or in combination of two or more kinds.
  • the carboxyl group-containing polymer preferably has a structural unit having an aromatic ring (preferably an aromatic hydrocarbon ring).
  • a structural unit derived from a (meth)acrylate having an aromatic ring specifically, benzyl (meth)acrylate, phenethyl (meth)acrylate, or phenoxyethyl (meth)acrylate, etc. can be mentioned.
  • the content of the structural unit having an aromatic ring is preferably 0 to 97 mol%, more preferably 0 to 95 mol%, and even more preferably 0 to 90 mol%, when the total of all structural units of the carboxy group-containing polymer is 100 mol%.
  • the aromatic ring-containing structural unit may use one type alone, or two or more types in combination.
  • the carboxyl group-containing polymer also preferably has a structural unit having an alicyclic structure.
  • alicyclic structures include a tricyclo[5.2.1.0 2,6 ]decane ring structure (also called tetrahydrodicyclopentadiene; the monovalent group is dicyclopentanyl), a tricyclo[5.2.1.0 2,6 ]decane-3-ene ring structure (also called 5,6-dihydrodicyclopentadiene; the monovalent group is dicyclopentenyl), an isobornane ring structure (the monovalent group is isobornyl), an adamantane ring structure (the monovalent group is adamantyl), and a cyclohexane ring structure (the monovalent group is cyclohexyl).
  • Examples of the structural unit having an alicyclic structure include structural units derived from (meth)acrylates having an alicyclic structure, specifically, structural units derived from dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, cyclohexyl (meth)acrylate, etc.
  • the content of the structural unit having an alicyclic structure is preferably 0 to 99 mol%, more preferably 10 to 90 mol%, even more preferably 10 to 70 mol%, particularly preferably 20 to 55 mol%, and especially preferably 25 to 55 mol%, when the total of all structural units of the carboxy group-containing polymer is 100 mol%.
  • the structural unit having an alicyclic structure may be used alone or in combination of two or more kinds.
  • the carboxyl group-containing polymer may have other structural units in addition to the above-mentioned structural units.
  • An example of the other structural unit is a structural unit derived from methyl (meth)acrylate.
  • the content of the other structural units in the carboxy group-containing polymer is preferably 0 to 70 mol%, more preferably 0 to 50 mol%, and even more preferably 0 to 20 mol%, when the total of all structural units of the carboxy group-containing polymer is 100 mol%.
  • the other structural units may be used alone or in combination of two or more kinds.
  • the wavelength selective absorption layer contains a compound B (also simply referred to as "compound B" in the present invention) that forms a hydrogen bond with an acid group contained in the resin A and generates radicals when irradiated with ultraviolet light.
  • Compound B is preferably a compound having a structure in which basicity increases when it absorbs ultraviolet light and becomes excited. When the basicity of compound B increases in the excited state, the acid group contained in resin A can form a complex with compound B through stronger interaction, thereby making it possible to increase the efficiency of radical generation.
  • the structure of compound B capable of forming a hydrogen bond with the acid group contained in resin A may be the entire structure of compound B or a partial structure constituting a part of compound B.
  • Compound B may be a polymer compound (meaning a compound having a molecular weight of 5000 or more) or a low molecular compound (meaning a compound having a molecular weight of less than 5000), and is preferably a low molecular compound.
  • the molecular weight of compound B, which is a low molecular weight compound is less than 5000, preferably less than 1000, more preferably 300 or less, and even more preferably 250 or less. There is no particular restriction on the lower limit, but it is preferably 65 or more, more preferably 75 or more.
  • a preferred range for the molecular weight of compound B, which is a low molecular weight compound is, for example, 65 to 300, more preferably 75 to 250.
  • Compound B is preferably an aromatic compound because it has a large molar absorption coefficient for ultraviolet light.
  • the aromatic compound is a compound having one or more aromatic rings.
  • the aromatic ring may be present in only one or in a plurality of rings in the compound B. When a plurality of aromatic rings are present, for example, the aromatic rings may be present in a side chain of a polymer constituting the resin.
  • the aromatic ring may be either an aromatic hydrocarbon ring or an aromatic heterocycle, and it is preferable that compound B has at least an aromatic heterocycle.
  • compound B is a compound having one or more (e.g., 1 to 4) heteroatoms (at least one of nitrogen atom, oxygen atom, sulfur atom, etc.) as ring member atoms (ring constituent atoms), and it is preferable that compound B is a compound having one or more (e.g., 1 to 4) nitrogen atoms as ring member atoms.
  • an unsubstituted aromatic hydrocarbon ring does not correspond to compound B because it does not have the function of forming a hydrogen bond with the acid group contained in resin A and generating radicals upon irradiation with ultraviolet light.
  • an unsubstituted aromatic hydrocarbon ring in a form in which an unsubstituted aromatic hydrocarbon ring is bonded to a side chain of a polymer constituting a resin does not correspond to compound B because it does not have the function of forming a hydrogen bond with the acid group contained in resin A and generating radicals upon irradiation with ultraviolet light.
  • the aromatic ring preferably has 5 to 15 ring atoms.
  • aromatic ring examples include monocyclic aromatic rings such as a pyridine ring, a pyrazine ring, a pyrimidine ring, and a triazine ring; aromatic rings having two condensed rings such as a quinoline ring, an isoquinoline ring, a quinoxaline ring, and a quinazoline ring; and aromatic rings having three condensed rings such as an acridine ring, a phenanthridine ring, a phenanthroline ring, and a phenazine ring.
  • monocyclic aromatic rings such as a pyridine ring, a pyrazine ring, a pyrimidine ring, and a triazine ring
  • aromatic rings having two condensed rings such as a quinoline ring, an isoquinoline ring, a quinoxaline ring, and a quinazoline ring
  • aromatic rings having three condensed rings such as an acrid
  • the aromatic ring may have one or more (for example, 1 to 5) substituents, and examples of the substituents include an alkyl group, an aryl group, a halogen atom, an acyl group, an alkoxycarbonyl group, an arylcarbonyl group, a carbamoyl group, a hydroxy group, a cyano group, and a nitro group.
  • substituents include an alkyl group, an aryl group, a halogen atom, an acyl group, an alkoxycarbonyl group, an arylcarbonyl group, a carbamoyl group, a hydroxy group, a cyano group, and a nitro group.
  • the multiple substituents may be bonded to each other to form a non-aromatic ring.
  • the series of aromatic ring structures in which the above-mentioned multiple aromatic rings are bonded through a structure selected from a single bond, a carbonyl bond, and a multiple bond does not fall under the above-mentioned unsubstituted aromatic hydrocarbon ring, nor does it fall under the unsubstituted aromatic hydrocarbon ring in a form in which an unsubstituted aromatic hydrocarbon ring is bonded to a side chain of a polymer constituting the resin.
  • compound B include monocyclic aromatic compounds such as pyridine compounds (pyridine and pyridine derivatives), pyrazine compounds (pyrazine and pyrazine derivatives), pyrimidine compounds (pyrimidine and pyrimidine derivatives), and triazine compounds (triazine and triazine derivatives); compounds in which two rings are condensed to form an aromatic ring, such as quinoline compounds (quinoline and quinoline derivatives), isoquinoline compounds (isoquinoline and isoquinoline derivatives), quinoxaline compounds (quinoxaline and quinoxaline derivatives), and quinazoline compounds (quinazoline and quinazoline derivatives); and compounds in which three or more rings are condensed to form an aromatic ring, such as acridine compounds (acridine and acridine derivatives), phenanthridine compounds (phenanthridine and phenanthridine derivatives), phenanthroline compounds (phenanthroline and phenanthroline derivatives), and
  • the term "compound” is used to mean not only the compound itself, but also a compound having a substituent (referred to as a "derivative"), including an unsubstituted compound whose structure has been partially changed within a range that does not impair the effects of the present invention. It is presumed that these compounds B form complexes with the above-mentioned resin A, and when irradiated with ultraviolet light, generate two radical molecules through the following mechanism. 1) Compound B in an excited state is generated by absorbing ultraviolet light. 2) A hole moves from compound B in an excited state to resin A in a ground state (an electron of resin A moves to the orbital with the lower energy of the two half-occupied orbitals of compound B in an excited state).
  • compound B is preferably at least one of quinoline compounds (quinoline and quinoline derivatives) and isoquinoline compounds (isoquinoline and isoquinoline derivatives).
  • the substituents which these compounds may have are preferably an alkyl group, an aryl group, a halogen atom, an acyl group, an alkoxycarbonyl group, an arylcarbonyl group, a carbamoyl group, a hydroxy group, a cyano group, or a nitro group.
  • compound B When compound B is a polymer, it may be a polymer in which the specific structure is bonded to the polymer main chain via a single bond or a linking group.
  • Compound B, which is a polymer can be obtained, for example, by polymerizing a monomer having a heteroaromatic ring (specifically, a heteroaromatic ring having a vinyl group and/or a (meth)acrylate monomer having a specific structure (preferably a heteroaromatic ring). If necessary, it may be copolymerized with other monomers.
  • compound B examples include quinoline, 2-methylquinoline, 4-methylquinoline, 2,4-dimethylquinoline, 2-methyl-4-phenylquinoline, isoquinoline, 1-methylisoquinoline, 3-methylisoquinoline, and 1-phenylisoquinoline.
  • the content of compound B is preferably 0.1 to 50 mass %, more preferably 2.0 to 40 mass %, further preferably 4 to 35 mass %, and particularly preferably 8 to 30 mass %, relative to the total mass of the wavelength selective absorption layer in the light absorbing filter I of the present invention.
  • the pKaH pKa of the conjugate acid
  • the pKaH which is a measure of basicity of compound B, can be, for example, 2.0 to 13.0.
  • the pKaH is preferably 2.0 to 7.0, more preferably 3.0 to 6.0, and even more preferably 4.3 to 5.5.
  • the compound B may be used alone or in combination of two or more kinds.
  • the wavelength-selective absorption layer in the absorption filter of the present invention may contain, in addition to the resin A containing the dye acid group described above, a compound B that forms a hydrogen bond with the acid group contained in the resin A described above and generates radicals when irradiated with ultraviolet light, a resin other than the resin A described above, and a photoradical generator, and may further contain an anti-fading agent, a leveling agent (surfactant), and the like.
  • the photoradical generator means a compound other than the above-mentioned compound B, which generates radicals by ultraviolet irradiation.
  • the photoradical generator can be suitably used in the present invention as described in paragraphs [0118] to [0125] of WO 2023/068235.
  • the light absorbing filter of the present invention and “the radical generator (preferably the photoradical generator)” are to be read as "the wavelength selective absorption layer in the light absorbing filter of the present invention” and “the photoradical generator”, respectively.
  • the anti-fading agent is preferably one that does not inhibit decolorization due to ultraviolet irradiation, while having the effect of suppressing decomposition of the dye due to visible light.
  • the anti-fading agent used in the present invention can be the anti-fading agent described in paragraphs [0265] to [0280] of WO 2022/210444.
  • a leveling agent can be appropriately mixed into the wavelength selective absorption layer in the light absorption filter of the present invention.
  • the leveling agent a commonly used compound can be used, and in particular, a fluorine-containing surfactant is preferable. Specific examples include the compounds described in paragraphs [0028] to [0056] of the specification of JP-A-2001-330725.
  • the Megafac F (trade name) series manufactured by DIC Corporation can also be used.
  • the content of the leveling agent in the wavelength selective absorption layer in the light absorption filter of the present invention is appropriately adjusted depending on the purpose.
  • the wavelength selective absorption layer in the light absorption filter of the present invention may contain, in addition to the above-mentioned components, a low molecular weight plasticizer, an oligomer plasticizer, a retardation regulator, a deterioration inhibitor, an infrared absorbing agent, an antioxidant, a filler, a compatibilizer, and the like. Furthermore, the wavelength selective absorption layer in the light absorption filter of the present invention may contain a reaction accelerator or a reaction retarder described in paragraphs [0020] and [0021] of JP-A-09-286979.
  • the wavelength selective absorption layer in the light absorbing filter of the present invention can be prepared by a conventional method such as a solution casting method, a melt extrusion method, or a method (coating method) of forming a coating layer on a substrate film (support film) by any method, and can also be combined with stretching as appropriate.
  • the wavelength selective absorption layer in the light absorbing filter of the present invention is preferably prepared by a coating method.
  • a coating method As the above-mentioned solution casting method and melt extrusion method, the descriptions of the solution casting method and melt extrusion method in [0197] to [0203] of WO 2021/132674 can be applied as they are.
  • a solution of the material of the wavelength selective absorption layer is applied to the support film to form a coating layer.
  • a release agent or the like may be applied in advance to the surface of the support film as appropriate in order to control adhesion with the coating layer.
  • the coating layer can be used by peeling off the support film after laminating it with other members via an adhesive layer in a later step, or after laminating a gas barrier layer or the like without an adhesive layer in a later step. Any adhesive can be appropriately used as the adhesive constituting the adhesive layer.
  • the support film can be appropriately stretched together with the support film in a state where the solution of the material of the wavelength selective absorption layer is applied to the support film or the coating layer is laminated.
  • the solvent used in the solution of the material for the wavelength-selective absorption layer can be appropriately selected from the viewpoints of being able to dissolve or disperse the material for the wavelength-selective absorption layer, being able to easily form a uniform surface during the coating and drying processes, being able to ensure the stability of the liquid, having an appropriate saturated vapor pressure, etc.
  • the timing of adding the dye to the material of the wavelength selective absorption layer is not particularly limited as long as it is added at the time of film formation.For example, it may be added at the time of synthesis of the resin A, or it may be mixed with the material of the wavelength selective absorption layer when preparing the coating solution of the material of the wavelength selective absorption layer.The same applies when the wavelength selective absorption layer contains the compound B, etc.
  • the support film used to form the wavelength selective absorption layer by a coating method or the like preferably has a thickness of 5 to 100 ⁇ m, more preferably 10 to 75 ⁇ m, and even more preferably 15 to 55 ⁇ m.
  • the film thickness is equal to or greater than the above-mentioned preferable lower limit, sufficient mechanical strength is easily ensured, and malfunctions such as curling, wrinkling, and buckling are unlikely to occur.
  • the film thickness is equal to or less than the above-mentioned preferable upper limit
  • the surface pressure applied to the multilayer film is easily adjusted to an appropriate range, and adhesion malfunctions are unlikely to occur.
  • the surface energy of the support film is not particularly limited, but the adhesive strength between the wavelength selective absorption layer and the support film can be adjusted by adjusting the relationship between the surface energies of the material of the wavelength selective absorption layer and the coating solution, and the surface energy of the surface of the support film on which the wavelength selective absorption layer is formed. If the difference in surface energy is reduced, the adhesive strength tends to increase, and if the difference in surface energy is increased, the adhesive strength tends to decrease, and can be set appropriately.
  • the surface unevenness of the support film is not particularly limited, but can be adjusted for the purpose of preventing adhesion failure, for example, when a multilayer film of an adjacent layer, a wavelength selective absorption layer, and a support film is stored in a long roll form, depending on the relationship between the surface energy, hardness, and surface unevenness of the wavelength selective absorption layer and the surface energy and hardness of the surface of the support film opposite the side on which the wavelength selective absorption layer is formed. Increasing the surface unevenness tends to suppress adhesion failure, while decreasing the surface unevenness tends to reduce the surface unevenness of the wavelength selective absorption layer and the haze of the wavelength selective absorption layer, and can be set appropriately.
  • any material and film can be used as appropriate.
  • Specific materials include polyester-based polymers (including polyethylene terephthalate-based), olefin-based polymers, cycloolefin-based polymers, (meth)acrylic polymers, cellulose-based polymers, polyamide-based polymers, and the like.
  • appropriate surface treatments can be performed. For example, corona treatment, room temperature plasma treatment, saponification treatment, and the like can be performed to reduce the surface energy, and silicone treatment, fluorine treatment, olefin treatment, and the like can be performed to increase the surface energy.
  • the thickness of the wavelength selective absorption layer is not particularly limited, but is preferably 1 to 18 ⁇ m, more preferably 1 to 12 ⁇ m, even more preferably 1 to 8 ⁇ m, and particularly preferably 1 to 5 ⁇ m. If it is equal to or less than the above-mentioned preferable upper limit, the decrease in the degree of polarization due to the fluorescence emitted by the dye can be suppressed by adding the dye at a high concentration to a thin film. In addition, the effect of the quenching agent is easily manifested. On the other hand, if it is equal to or more than the above-mentioned preferable lower limit, the uniformity of the absorbance in the plane can be easily maintained.
  • a film thickness of 1 to 18 ⁇ m means that the thickness of the wavelength selective absorption layer is within the range of 1 to 18 ⁇ m no matter where it is measured. This also applies to film thicknesses of 1 to 12 ⁇ m, 1 to 8 ⁇ m, and 1 to 5 ⁇ m.
  • the film thickness can be measured using an electronic micrometer manufactured by Anritsu Corporation.
  • the wavelength selective absorption layer may be subjected to hydrophilization treatment by any glow discharge treatment, corona discharge treatment, or alkaline saponification treatment, among which corona discharge treatment is preferably used. It is also preferable to apply the methods disclosed in JP-A-6-94915 or JP-A-6-118232.
  • the obtained film may be subjected to a heat treatment process, a superheated steam contact process, an organic solvent contact process, etc. as necessary. Surface treatment may also be performed as appropriate.
  • a layer made of a pressure-sensitive adhesive composition having a base polymer such as a (meth)acrylic resin, a styrene resin, a silicone resin, or the like, to which a crosslinking agent such as an isocyanate compound, an epoxy compound, or an aziridine compound has been added can also be applied.
  • a base polymer such as a (meth)acrylic resin, a styrene resin, a silicone resin, or the like
  • a crosslinking agent such as an isocyanate compound, an epoxy compound, or an aziridine compound has been added
  • the description of the adhesive layer in the OLED display device described later can be applied.
  • the light absorbing filter of the present invention includes an adjacent layer disposed directly on at least one surface of the above-mentioned wavelength selective absorption layer, and this adjacent layer contains a resin containing a basic group.
  • the adjacent layer may be provided on only one side or both sides of the wavelength-selective absorption layer in the light-absorbing filter of the present invention or the optical filter of the present invention.
  • the adjacent layer is not particularly limited, and may be, for example, a layer containing a resin containing a basic group in a layer that is normally used in a display device such as an organic electroluminescence display device, an inorganic electroluminescence display device, or a liquid crystal display device (hereinafter referred to as a "layer normally used in a display device"), which will be described later.
  • a resin containing a basic group may be contained in a gas barrier layer, a diffusion-preventing layer, a pressure-sensitive adhesive layer, or an antireflection layer, the adhesive layer, or a refractive index adjusting layer, which will be described later, to form the adjacent layer.
  • a layer that is different from the layer normally used in the display device and contains a resin that contains a basic group can be incorporated as the adjacent layer.
  • the resin containing a basic group contained in the adjacent layer is unevenly distributed in the adjacent layer near the interface between the adjacent layer and the wavelength selective absorption layer, and can improve adhesion by forming a hydrogen bond with the acid group contained in the resin A contained in the wavelength selective absorption layer.
  • the resin containing a basic group contained in the adjacent layer is not particularly limited as long as it is a resin containing a group or structure exhibiting basicity (in the present invention, these are collectively referred to as "basic group”) and can improve the adhesion of the light absorbing filter of the present invention.
  • the resin containing a basic group means that the polymer constituting the resin contains a basic group.
  • the polymer constituting the resin containing a basic group may be an organic basic group or an inorganic basic group, and is preferably a polymer containing an organic basic group, and more preferably a polymer containing an organic basic group containing a nitrogen atom (a polymer containing a nitrogen-containing basic group).
  • the organic basic group preferably has a structure in which pKaH (pKa of the conjugate acid) is 4 or more. There is no particular upper limit to the pKa of the conjugate acid, but practically it is 13 or less.
  • the pKa has the same meaning as the pKa of the compound B described above.
  • organic basic groups having a pKaH examples include unsubstituted amino groups (-NH 2 , primary amino groups), substituted secondary or tertiary amino groups (amino groups having at least one substituent), and nitrogen-containing aromatic ring groups.
  • the substituents on the nitrogen atoms of the above-mentioned substituted secondary or tertiary amino groups may be bonded to each other to form a ring structure other than an aromatic ring.
  • organic basic group having a pKaH (pKa of the conjugate acid) of 4 or more include groups consisting of nitrogen-containing aromatic rings such as guanidine, pyridine, aminopyridine, aminoalkylpyridine, aminopyrrolidine, indazole, imidazole, pyrazole, pyrazine, pyrimidine, purine, imidazoline, pyrazoline, piperazine, aminomorpholine, and aminoalkylmorpholine.
  • Preferred examples of the substituent that these organic basic groups may have include unsubstituted amino groups, alkylamino groups, aminoaryl groups, arylamino groups, alkyl groups (particularly preferred as the substituted alkyl group are aminoalkyl groups), alkoxy groups, acyl groups, acyloxy groups, aryl groups, aryloxy groups, nitro groups, hydroxy groups, and cyano groups.
  • organic basic groups include guanidine, 1,1-dimethylguanidine, 1,1,3,3-tetramethylguanidine, imidazole, 2-methylimidazole, 4-methylimidazole, N-methylimidazole, 2-phenylimidazole, 4,5-diphenylimidazole, 2,4,5-triphenylimidazole, 2-aminopyridine, 3-aminopyridine, 4-aminopyridine, 2-dimethylaminopyridine, 4-dimethylaminopyridine, 2-diethylaminopyridine, 2-(aminomethyl)pyridine, 2-amino-3-methylpyridine, 2-amino-4-methylpyridine, 2-amino-5-methylpyridine, 2-amino-6-methylpyridine, 3-aminoethylpyridine, and the like.
  • nitrogen-containing aromatic ring examples include lysine, 4-aminoethylpyridine, 3-aminopyrrolidine, piperazine, N-(2-aminoethyl)piperazine, N-(2-aminoethyl)piperidine, 4-amino-2,2,6,6-tetramethylpiperidine, 4-piperidinopiperidine, 2-iminopiperidine, 1-(2-aminoethyl)pyrrolidine, pyrazole, 3-amino-5-methylpyrazole, 5-amino-3-methyl-1-p-tolylpyrazole, pyrazine, 2-(aminomethyl)-5-methylpyrazine, pyrimidine, 2,4-diaminopyrimidine, 4,6-dihydroxypyrimidine, 2-pyrazoline, 3-pyrazoline, N-aminomorpholine, and N-(2-aminoethyl)morpholine.
  • Examples of the polymer having a nitrogen-containing aromatic ring group as the organic basic group include the above-mentioned polymers having a group consisting of a nitrogen-containing aromatic ring, and preferred examples include polyvinylpyridine.
  • polymeric polyamines examples include polyethyleneimine and polymeric polyamines other than polyethyleneimine (hereinafter also simply referred to as "polymeric polyamines"). It is preferable to use at least one of polyethyleneimine and polymeric polyamines.
  • the polymeric polyamine means a polymer having two or more amino groups selected from the above-mentioned unsubstituted amino group and secondary to tertiary amino groups having a substituent.
  • the polymeric polyamine is preferably a linear polymer having two or more amino groups selected from the above-mentioned unsubstituted amino group and secondary to tertiary amino groups having a substituent, more preferably a linear polymer containing a structural unit having an amino group selected from the above-mentioned unsubstituted amino group and secondary to tertiary amino groups having a substituent in a side chain, even more preferably a linear polymer containing a structural unit having an unsubstituted amino group in a side chain, and particularly preferably a linear vinyl polymer containing a structural unit having an unsubstituted amino group in a side chain.
  • the above-mentioned structural unit having an unsubstituted amino group on the side chain is not particularly limited, and examples thereof include structural units derived from N-vinylamine or allylamine, with structural units derived from N-vinylamine or allylamine being preferred.
  • the structural unit having a substituted secondary or tertiary amino group on the side chain is not particularly limited, and examples thereof include a structural unit derived from an N-vinylamine derivative such as N-vinylformamide, a structural unit derived from diallylamine, and a structural unit derived from an allylamine derivative such as an alkoxycarbonylated allylamine or a ureated allylamine.
  • the polymeric polyamine may also have a constituent unit other than the above-mentioned constituent unit having an unsubstituted amino group on a side chain and the constituent unit having a substituted secondary or tertiary amino group on a side chain, and examples thereof include constituent units derived from diallylamine derivatives such as diallyldialkylammonium salts.
  • the content of the structural unit having an amino group selected from the above-mentioned unsubstituted amino group and secondary or tertiary amino group having a substituent at a side chain (preferably the structural unit having the above-mentioned unsubstituted amino group at a side chain) in the linear polymeric polyamine is, for example, preferably 10 to 100 mol %, more preferably 20 to 100 mol %, and even more preferably 50 to 100 mol %.
  • polyethyleneimine for example, Epomin SP-200, HM-2000, P-1000, and P-3000 manufactured by Nippon Shokubai Co., Ltd., and polyethyleneimine 10000 and 70000 manufactured by Junsei Chemical Co., Ltd. can be preferably used.
  • Polyethyleneimine manufactured by Fujifilm Wako Pure Chemical Industries, Ltd. can also be preferably used.
  • polymeric polyamine for example, PVAM-0570B, PVAM-0595B, and PVDL manufactured by Mitsubishi Chemical Corporation, and PAA-15C, PAA-25, PAA-1222, PAA-U5000, PAA-N5000, PAS-21, and PAA-D11 manufactured by Nittobo Medical Co., Ltd., all of which are trade names, can be preferably used.
  • the weight average molecular weight (Mw) of the polymer constituting the resin containing the basic group is preferably 5,000 or more, more preferably 5,000 to 200,000, and even more preferably 5,000 to 150,000.
  • the content of the resin containing a basic group in the adjacent layer is preferably 0.5 parts by mass or more, more preferably 0.75 parts by mass or more, even more preferably 1.0 parts by mass or more, and particularly preferably 1.5 parts by mass or more, relative to 100 parts by mass of the total of the components other than the resin containing a basic group that constitutes the adjacent layer.
  • the upper limit is preferably 45 parts by mass or less, more preferably 30 parts by mass or less, even more preferably 20 parts by mass or less, and particularly preferably 15 parts by mass or less.
  • the preferred range of the content of the resin containing a basic group in the adjacent layer is, for example, 0.5 to 45 parts by mass, more preferably 0.75 to 30 parts by mass, even more preferably 1.0 to 20 parts by mass, and particularly preferably 1.5 to 15 parts by mass, relative to 100 parts by mass of the total of the components other than the resin containing a basic group that constitutes the adjacent layer.
  • the content of the resin containing a basic group in the total mass of the adjacent layer (100 mass%) is, for example, preferably 0.5 to 30 mass%, more preferably 0.75 to 25 mass%, even more preferably 1.0 to 15 mass%, and particularly preferably 1.5 to 10 mass%.
  • the film thickness of the light-absorbing filter of the present invention is not particularly limited, but is preferably from 1.5 to 20 ⁇ m, more preferably from 1.5 to 15 ⁇ m, and even more preferably from 2 to 10 ⁇ m.
  • a film thickness of 1.5 to 20 ⁇ m means that the thickness of the light-absorbing filter of the present invention is within the range of 1.5 to 20 ⁇ m no matter where it is measured. This also applies to film thicknesses of 1.5 to 15 ⁇ m and 2 to 10 ⁇ m.
  • the film thickness can be measured using an electronic micrometer manufactured by Anritsu Corporation.
  • the absorbance at the maximum absorption wavelength at which the dye exhibits the highest absorbance is preferably 0.3 or more, more preferably 0.5 or more, and even more preferably 0.7 or more.
  • the absorbance of the light absorption filter of the present invention can be adjusted by the type, amount added, or film thickness of the dye contained in the wavelength selective absorption layer in the light absorption filter of the present invention.
  • the decolorization rate of the light-absorbing filter of the present invention due to ultraviolet irradiation is preferably 35% or more, more preferably 45% or more, even more preferably 55% or more, and particularly preferably 70% or more. There is no particular upper limit, and it is also preferable that the upper limit is 100%.
  • the decolorization rate is calculated from the Ab( ⁇ max ) values before and after the ultraviolet irradiation test according to the following formula.
  • Decolorization rate (%) 100- (Ab( ⁇ max ) after ultraviolet irradiation/Ab( ⁇ max ) before ultraviolet irradiation) ⁇ 100
  • the ultraviolet irradiation test is performed by irradiating the light absorbing filter with ultraviolet light at an illuminance of 100 mW/ cm2 and an irradiation dose of 2000 mJ/ cm2 at room temperature (25°C) using an ultra-high pressure mercury lamp (e.g., UL750, manufactured by HOYA Corporation) under atmospheric pressure (101.33 kPa).
  • an ultra-high pressure mercury lamp e.g., UL750, manufactured by HOYA Corporation
  • the above-mentioned absorbance, ultraviolet irradiation test and decolorization rate can be measured and calculated for the light-absorbing filter of the present invention by the methods described in the Examples.
  • the light-absorbing filter of the present invention has a decolorizing property
  • absorption secondary absorption
  • the presence or absence of absorption due to a new colored structure accompanying decomposition of the dye can be confirmed based on the ratio of absorbance at a specific wavelength to the above Ab( ⁇ max ).
  • the specific wavelength is selected as the wavelength at which the dye shows almost no absorption before UV irradiation and at which new absorption due to decomposition of the dye is observed.
  • the presence or absence of absorption originating from a new colored structure accompanying decomposition of the dye can be confirmed based on the ratio of absorbance at a wavelength of 450 nm (hereinafter also simply referred to as "Ab(450)”) to the above Ab( ⁇ max ). That is, the smaller the value obtained by subtracting the ratio of (I) below from the ratio of (II) below, the less absorption originating from a new colored structure accompanying decomposition of the dye is occurring, and this value is preferably less than 8.5%, more preferably 7.0% or less, and even more preferably 5.0% or less.
  • the light absorbing filter of the present invention When the light absorbing filter of the present invention has decolorization properties, the light absorbing filter of the present invention can exhibit excellent decolorization properties by having the above-mentioned decolorization rate and the value confirming the presence or absence of absorption due to the new colored structure accompanying the decomposition of the dye both satisfy the preferred ranges.
  • the light absorbing portion having a light absorbing effect in the optical filter of the present invention satisfies the above description of Ab( ⁇ max ) for the light absorbing filter of the present invention.
  • the light absorbing filter of the present invention may appropriately have any optically functional film such as the gas barrier layer described below within the scope of not impairing the effects of the present invention.
  • the above-mentioned optional optical functional film is not particularly limited in terms of optical properties and materials, but a film containing (or having as its main component) at least one of cellulose ester resin, acrylic resin, cyclic olefin resin, and polyethylene terephthalate resin can be preferably used. Note that, either an optically isotropic film or an optically anisotropic retardation film can be used.
  • a film containing a cellulose ester resin for example, Fujitac TD80UL (trade name, manufactured by Fujifilm Corporation) can be used.
  • the film containing an acrylic resin include an optical film containing a (meth)acrylic resin containing a styrene-based resin described in Japanese Patent No. 4,570,042, an optical film containing a (meth)acrylic resin having a glutarimide ring structure in the main chain described in Japanese Patent No. 5,041,532, an optical film containing a (meth)acrylic resin having a lactone ring structure described in Japanese Patent Laid-Open No.
  • the light absorbing filter of the present invention may have a gas barrier layer on at least one side of the wavelength selective absorption layer.
  • the light absorbing filter of the present invention can be a light absorbing filter that realizes both excellent decolorization property and excellent light fastness, and can be suitably used for the production of the optical filter described later.
  • the material forming the gas barrier layer is not particularly limited, and examples thereof include organic materials (preferably crystalline resins) such as polyvinyl alcohol and polyvinylidene chloride, organic-inorganic hybrid materials such as sol-gel materials, and inorganic materials such as SiO 2 , SiO x , SiON, SiN x and Al 2 O 3.
  • organic materials preferably crystalline resins
  • organic-inorganic hybrid materials such as sol-gel materials
  • inorganic materials such as SiO 2 , SiO x , SiON, SiN x and Al 2 O 3.
  • the gas barrier layer may be a single layer or a multilayer, and in the case of a multilayer, examples of the gas barrier layer include an inorganic dielectric multilayer film and a multilayer film in which organic materials and inorganic materials are alternately laminated.
  • the light absorbing filter of the present invention has a gas barrier layer at least on the surface that comes into contact with air when the light absorbing filter of the present invention is used, and this makes it possible to suppress a decrease in the light absorption intensity (absorbance) of the dye in the light absorbing filter of the present invention.
  • the gas barrier layer may be provided on only one surface of the light absorbing filter of the present invention, or on both surfaces.
  • the gas barrier layer when configured to contain a crystalline resin, it is preferable that the gas barrier layer contains a crystalline resin, has a layer thickness of 0.1 ⁇ m to 10 ⁇ m, and has an oxygen permeability of 60 cc/ m2 ⁇ day ⁇ atm or less.
  • the "crystalline resin” is a resin that has a melting point at which it undergoes a phase transition from crystal to liquid when the temperature is increased, and is capable of imparting gas barrier properties related to oxygen gas to the gas barrier layer.
  • the crystalline resin contained in the gas barrier layer is not particularly limited as long as it is a crystalline resin having gas barrier properties and can impart the desired oxygen permeability to the gas barrier layer.
  • the crystalline resin include polyvinyl alcohol and polyvinylidene chloride, with polyvinyl alcohol being preferred since the crystalline portion can effectively suppress gas permeation.
  • the polyvinyl alcohol may be modified or unmodified.
  • modified polyvinyl alcohol include modified polyvinyl alcohol into which a group such as an acetoacetyl group or a carboxy group has been introduced.
  • the saponification degree of the polyvinyl alcohol is preferably 80.0 mol% or more, more preferably 90.0 mol% or more, even more preferably 97.0 mol% or more, and particularly preferably 98.0 mol% or more, from the viewpoint of further improving the oxygen gas barrier property. There is no particular upper limit, but 99.99 mol% or less is practical.
  • the saponification degree of the polyvinyl alcohol is a value calculated based on the method described in JIS (Japanese Industrial Standards) K 6726 1994.
  • the gas barrier layer may contain any component normally contained in a gas barrier layer, provided that the effect of the present invention is not impaired.
  • the gas barrier layer may contain an amorphous resin material, an organic-inorganic hybrid material such as a sol-gel material, or an inorganic material such as SiO 2 , SiO x , SiON, SiN x and Al 2 O 3 .
  • the gas barrier layer may contain water, an organic solvent, and other solvents resulting from the manufacturing process, as long as the effects of the present invention are not impaired.
  • the content of the crystalline resin in the gas barrier layer is, for example, preferably 90% by mass or more, and more preferably 95% by mass or more, relative to 100% by mass of the total mass of the gas barrier layer. There is no particular upper limit, but it may be 100% by mass.
  • the content of the crystalline resin in the gas barrier layer is preferably 70 to 99.5 mass%, more preferably 75 to 99.25 mass%, even more preferably 85 to 99 mass%, and particularly preferably 90 to 98.5 mass%.
  • the oxygen permeability of the gas barrier layer is preferably 60cc/ m2 ⁇ day ⁇ atm or less, more preferably 50cc/ m2 ⁇ day ⁇ atm or less, even more preferably 30cc/ m2 ⁇ day ⁇ atm or less, particularly preferably 10cc/ m2 ⁇ day ⁇ atm or less, particularly preferably 5cc/ m2 ⁇ day ⁇ atm or less, and most preferably 1cc/ m2 ⁇ day ⁇ atm or less.
  • the practical lower limit is 0.001cc/ m2 ⁇ day ⁇ atm or more, and preferably exceeds, for example, 0.05cc/ m2 ⁇ day ⁇ atm.
  • the oxygen permeability of the gas barrier layer is a value measured based on a gas permeability test method based on JIS K 7126-2 2006.
  • a measuring device for example, an oxygen permeability measuring device, OX-TRAN2/21 (product name) manufactured by MOCON Co., Ltd. can be used.
  • the measurement conditions are a temperature of 25° C. and a relative humidity of 50%.
  • the thickness of the gas barrier layer is preferably 0.1 ⁇ m to 5 ⁇ m, and more preferably 0.1 ⁇ m to 4.0 ⁇ m.
  • the thickness of the gas barrier layer is measured by a method of taking a cross-sectional photograph using a field emission scanning electron microscope S-4800 (trade name) manufactured by Hitachi High-Technologies Corporation or the like.
  • the crystallinity of the crystalline resin contained in the gas barrier layer is preferably 25% or more, more preferably 40% or more, and even more preferably 45% or more. There is no particular upper limit, but it is practical to set the upper limit to 55%, and preferably to 50%.
  • the degree of crystallinity of the crystalline resin contained in the gas barrier layer is a value measured and calculated by the following method based on the method described in J. Appl. Pol. Sci., 81, 762 (2001). Using a DSC (differential scanning calorimeter), the sample peeled off from the gas barrier layer is heated from 20° C. to 260° C. at a rate of 10° C./min to measure the heat of fusion 1.
  • the heat of fusion 2 of a perfect crystal is determined from the value described in J. Appl. Pol. Sci., 81, 762 (2001).
  • the obtained heat of fusion 1 and heat of fusion 2 are used to calculate the degree of crystallinity according to the following formula.
  • [Crystallization degree (%)] ([Heat of fusion 1] / [Heat of fusion 2]) x 100
  • the heat of fusion 1 and the heat of fusion 2 may be expressed in the same unit, which is usually Jg ⁇ 1 .
  • the method for forming the gas barrier layer is not particularly limited, but may be a conventional method, for example, in the case of an organic material, a casting method such as spin coating and slit coating may be used. In addition, a method of laminating a commercially available resin gas barrier film or a resin gas barrier film that has been previously prepared to the light absorbing filter of the present invention may be used. In the case of an inorganic material, a plasma enhanced chemical vapor deposition (CVD) method, a sputtering method, and a vapor deposition method may be used.
  • CVD plasma enhanced chemical vapor deposition
  • the above-mentioned gas barrier layer on the light-absorbing filter of the present invention for example, a method of directly forming the above-mentioned gas barrier layer on the light-absorbing filter of the present invention produced by the above-mentioned production method can be mentioned.
  • the optional optical functional film it is also preferable to laminate the film via a pressure-sensitive adhesive layer.
  • the above-mentioned gas barrier layer or optically functional film is provided as an adjacent layer in the light absorbing filter of the present invention, it can be provided in the same manner as above, except that it is provided so as to be a gas barrier layer containing a resin containing a basic group, not to the light absorbing filter of the present invention but to the wavelength selective absorption layer in the light absorbing filter of the present invention.
  • the light absorbing filter of the present invention may have a diffusion-preventing layer between the wavelength selective absorption layer and the support.
  • the diffusion-preventing layer can suppress the components in the wavelength selective absorption layer from diffusing into the support, and in particular, in the light absorbing filter I of the present invention, can improve the decolorization property due to ultraviolet irradiation.
  • the diffusion of the wavelength selective absorption layer components into the support may occur during the formation of the wavelength selective absorption layer and during the process after the formation of the wavelength selective absorption layer. In particular, during the formation of the wavelength selective absorption layer, the support swells due to the solvent in the wavelength selective absorption layer coating liquid, and the free volume in the support increases, which has a large effect.
  • the diffusion-preventing layer has a low affinity to the solvent used during the formation of the wavelength selective absorption layer.
  • the resin constituting the diffusion-preventing layer is a resin with a low affinity to organic solvents, i.e., a water-soluble resin.
  • the affinity between the solvent used in the wavelength selective absorption layer and the resin constituting the diffusion-preventing layer can be evaluated by the solubility parameter ⁇ t calculated by the Hoy method.
  • the solubility parameter ⁇ t can be calculated, for example, by the method described in the literature "Properties of Polymers 3rd , ELSEVIER, (1990)" (pages 214-220, "2) Method of Hoy (1985, 1989)".
  • the absolute value of the difference between the ⁇ t value of the solvent used when forming the wavelength selective absorption layer and the ⁇ t value of the resin constituting the diffusion-preventing layer is preferably 1.0 or more, more preferably 2.0 or more, and even more preferably 3.0 or more.By adjusting the absolute value of the difference between the ⁇ t value of the solvent used when forming the wavelength selective absorption layer and the ⁇ t value of the resin constituting the diffusion-preventing layer to be equal to or more than the above-mentioned preferred value, when the liquid forming the wavelength selective absorption layer is applied onto the diffusion-preventing layer, the solvent contained in the liquid forming the wavelength selective absorption layer is suppressed from penetrating the diffusion-preventing layer, and the swelling of the support is effectively suppresse
  • the resin constituting the diffusion-preventing layer is preferably a water-soluble resin.
  • the water-soluble resin may be either a thermosetting resin or a thermoplastic resin, and if it is a thermoplastic resin, it may be crystalline or amorphous.
  • the water-soluble resin may preferably be polyvinyl alcohol, polyvinylpyridine, (meth)acrylic resin, polyurethane, polyester, epoxy resin, cellulose resin, etc. These water-soluble resins may be at least partially modified.
  • the polyvinyl alcohol may be modified or unmodified. Examples of modified polyvinyl alcohol include modified polyvinyl alcohol into which an acetoacetyl group, a carboxy group, or the like has been introduced.
  • the degree of saponification of the polyvinyl alcohol is preferably 60.0 mol% or more, more preferably 80.0 mol% or more, and even more preferably 90.0 mol% or more, from the viewpoint of further improving the barrier property (permeation suppression performance) of the organic solvent. There is no particular upper limit, but 99.99 mol% or less is practical.
  • the degree of saponification of the polyvinyl alcohol is a value calculated based on the method described in JIS K 6726 (1994).
  • the (meth)acrylic resin may be any resin containing at least one of a structural unit derived from (meth)acrylic acid and a structural unit derived from a (meth)acrylic acid ester, and is preferably a resin containing a structural unit derived from (meth)acrylic acid.
  • the proportion of the structural unit derived from (meth)acrylic acid in the total structural units constituting the (meth)acrylic resin is preferably 70 to 100 mol%, more preferably 80 to 100 mol%, and even more preferably 90 to 100 mol%.
  • the crystalline portion can effectively suppress the transmission of solvent molecules and swelling due to the organic solvent used in the wavelength selective absorption layer is unlikely to occur, it is preferable to use at least one of polyvinyl alcohol and (meth)acrylic resin as the resin constituting the diffusion-impeding layer, and it is more preferable to use at least one of polyvinyl alcohol and poly(meth)acrylic acid.
  • the content of the resin (preferably the water-soluble resin) in the diffusion-preventing layer is, for example, preferably 90% by mass or more, more preferably 95% by mass or more. There is no particular upper limit, but it may be 100% by mass.
  • the thickness of the diffusion-preventing layer is preferably 0.1 to 5.0 ⁇ m, and more preferably 0.2 to 4.0 ⁇ m, from the viewpoint of further improving the diffusion-preventing ability.
  • the method for forming the diffusion-preventing layer is not particularly limited, but examples thereof include a method in which the diffusion-preventing layer is formed on a support by a casting method such as spin coating or slit coating according to a conventional method.
  • the solvent used in this case can be used without any particular limitation as long as the desired diffusion-preventing layer can be obtained.
  • the resin constituting the diffusion-preventing layer is a water-soluble resin
  • water-soluble solvents such as water, alcohols such as ethanol and isopropyl alcohol can be preferably used.
  • the description of the support in the coating method described above can be applied as it is.
  • fine particles may be added to impart slipperiness and prevent blocking, within a range that does not impair the effects of the present invention.
  • silica silicon dioxide, SiO 2
  • fine particles such as titanium dioxide, aluminum oxide, zirconium oxide, calcium carbonate, talc, clay, calcined kaolin, calcined calcium silicate, hydrated calcium silicate, aluminum silicate, magnesium silicate, and calcium phosphate may be used.
  • examples of commercially available fine particles include R972 and NX90S (both are product names manufactured by Nippon Aerosil Co., Ltd.).
  • These fine particles function as a so-called matting agent, and the addition of the fine particles forms minute irregularities on the surface of the light-absorbing filter of the present invention, and these irregularities prevent the light-absorbing filters of the present invention or the light-absorbing filter of the present invention and other films, etc. from sticking to each other even when they are overlapped, and ensure slipperiness.
  • the light-absorbing filter of the present invention contains a matting agent in the form of fine particles, the minute irregularities caused by protrusions of fine particles protruding from the filter surface have a particularly large effect of improving slip properties and blocking properties when the number of protrusions having a height of 30 nm or more is 104 /mm2 or more .
  • the matting agent fine particles
  • Methods for applying fine particles to the surface layer include means such as multilayer casting and coating.
  • the content of the matting agent in the light-absorbing filter of the present invention is appropriately adjusted depending on the purpose.
  • the optical filter of the present invention can be obtained by exposing the light-absorbing filter of the present invention to ultraviolet light through a mask.
  • the light absorption filters of the present invention having decolorization properties include a light absorption filter I of the present invention in which the wavelength selective absorption layer contains a resin A containing the above-mentioned dye and the above-mentioned acid group, and the above-mentioned compound B which forms a hydrogen bond with the acid group contained in this resin A and generates radicals when irradiated with ultraviolet light, and a light absorption filter containing a resin A containing the above-mentioned dye and the above-mentioned acid group in the wavelength selective absorption layer, and the above-mentioned photoradical generator.
  • the light-absorbing filter of the present invention when the light-absorbing filter of the present invention is simply referred to, it means the light-absorbing filter of the present invention having a decolorizing property.
  • the wavelength-selective absorption layer in the optical filter of the present invention has light-absorbing sites that have a light-absorbing effect and sites where the light-absorbency has been eliminated (light-absorbency-eliminated sites) in accordance with a pattern of mask exposure (hereinafter also referred to as "mask pattern").
  • the masked portions of the wavelength selective absorption layer in the light absorbing filter of the present invention are not exposed and exist as light absorbing portions having a light absorbing effect, whereas the unmasked portions are exposed and become portions where light absorbency has disappeared.
  • the light absorbing moiety can exhibit a desired absorbance.
  • the light-absorption-eliminating site can exhibit optical properties close to colorless since the wavelength-selective absorption layer in the light-absorbing filter of the present invention exhibits an excellent decolorization rate and, moreover, secondary absorption accompanying decomposition of the dye hardly occurs.
  • the optical filter of the present invention can be obtained by irradiating the light-absorbing filter of the present invention with ultraviolet light and exposing it through a mask.
  • the mask pattern can be appropriately adjusted so as to obtain the optical filter of the present invention having a desired pattern composed of light-absorbing sites and non-light-absorbing sites.
  • the conditions of ultraviolet irradiation can be appropriately adjusted so as to obtain the optical filter of the present invention having a light-absorption-disappearing portion.
  • the pressure conditions can be atmospheric pressure (101.33 kPa)
  • the temperature conditions can be mild temperature conditions such as room temperature (10 to 30°C) without heating
  • the lamp output can be 80 to 320 W/cm
  • the lamp used can be an air-cooled metal halide lamp, a mercury lamp such as an ultra-high pressure mercury lamp, or the like.
  • the irradiation dose can be 200 to 2000 mJ/ cm2 .
  • the optical filter of the present invention may have an optically functional film as described in the light-absorbing filter of the present invention.
  • the optical filter of the present invention may have a layer containing an ultraviolet absorbing agent.
  • the ultraviolet absorbing agent any commonly used compound can be used without any particular limitation, and for example, the ultraviolet absorbing agent in the ultraviolet absorbing layer described below can be mentioned.
  • the resin constituting the layer containing an ultraviolet absorbing agent is also without any particular limitation, and for example, the resin in the ultraviolet absorbing layer described below can be mentioned.
  • the content of the ultraviolet absorbing agent in the layer containing the ultraviolet absorbing agent is appropriately adjusted depending on the purpose.
  • the optical filter of the present invention can be used in displays such as organic electroluminescence displays, inorganic electroluminescence displays, and liquid crystal displays.
  • displays such as organic electroluminescence displays, inorganic electroluminescence displays, and liquid crystal displays.
  • the optical filter of the present invention includes a gas barrier layer, it is preferable that the gas barrier layer is disposed on the external light side relative to the wavelength selective absorption layer.
  • the organic electroluminescence display device of the present invention also called an organic EL (electroluminescence) display device or OLED (organic light emitting diode) display device, and in the present invention, also abbreviated as an OLED display device
  • OLED display device is provided with the optical filter of the present invention.
  • the OLED display device of the present invention includes the optical filter of the present invention, the other configurations of the OLED display device that are commonly used can be used without any particular limitations.
  • the configuration is not particularly limited, but may be, for example, a layer including glass, a layer including a thin film transistor (TFT), an OLED display element, a barrier film, a color filter, glass, an adhesive layer, and the present invention, in that order from the side opposite to the external light.
  • the display device include the optical filters and surface films.
  • the OLED display element has a structure in which an anode electrode, a light-emitting layer, and a cathode electrode are laminated in this order.
  • the description in JP 2014-132522 A can also be referred to.
  • the color filter in addition to a normal color filter, a color filter having quantum dots laminated thereon can also be used.
  • a resin film may be used.
  • the surface of the optical filter of the present invention facing the external light may be bonded to an optically functional film having an antireflection layer, etc., via an adhesive layer.
  • the surface of the optical filter of the present invention facing the opposite side to the external light is preferably bonded to glass (substrate) via an adhesive layer.
  • the adhesive layer the description relating to the adhesive layer and the formation method in the OLED display device described in [0239] to [0290] of WO 2021/132674 can be applied as it is.
  • the pressure-sensitive adhesive composition described in WO 2021/132674 preferably contains the above-mentioned ultraviolet absorber in terms of the light resistance of the optical filter.
  • the optical filter of the present invention may be attached to any optically functional film via an adhesive layer on the surface facing the external light side, and is preferably attached to glass (substrate) via an adhesive layer on the surface facing the opposite side to the external light side.
  • the method for forming the pressure-sensitive adhesive layer is not particularly limited, and examples of the method that can be used include a method in which an adhesive composition is applied to the light-absorbing filter or optical filter of the present invention by a conventional means such as a bar coater, followed by drying and curing; and a method in which an adhesive composition is first applied to the surface of a release substrate, dried, and then the pressure-sensitive adhesive layer is transferred to the light-absorbing filter of the present invention using the release substrate, followed by aging and curing.
  • the release substrate is not particularly limited, and any release substrate can be used, for example the support film in the above-mentioned method for producing the light-absorbing filter of the present invention. Other conditions such as coating, drying, aging and curing can be appropriately adjusted based on conventional methods.
  • the inorganic electroluminescence display device of the present invention (also referred to as an inorganic EL (electroluminescence) display device, and in the present invention, also abbreviated as inorganic EL display device) includes the optical filter of the present invention.
  • the inorganic EL display device of the present invention includes the optical filter of the present invention, other configurations of inorganic EL display devices that are commonly used can be used without any particular limitations.
  • the inorganic EL element and inorganic electroluminescence display device described in JP-A-2005-338640 can be preferably applied.
  • the liquid crystal display device of the present invention includes the optical filter of the present invention.
  • the optical filter of the present invention may be used as at least one of a polarizing plate protective film and a pressure-sensitive adhesive layer as described below, and may be included in a backlight unit used in a liquid crystal display device.
  • the liquid crystal display device preferably includes the optical filter of the present invention, a polarizing plate including a polarizer and a polarizing plate protective film, an adhesive layer, and a liquid crystal cell, and the polarizing plate is preferably attached to the liquid crystal cell via the adhesive layer.
  • the optical filter of the present invention may also serve as the polarizing plate protective film or the adhesive layer.
  • the liquid crystal display device can be divided into a case where it includes a polarizing plate including a polarizer and the optical filter of the present invention (polarizing plate protective film), an adhesive layer, and a liquid crystal cell, and a case where it includes a polarizing plate including a polarizer and a polarizing plate protective film, the optical filter of the present invention (adhesive layer), and a liquid crystal cell.
  • FIG. 1 is a schematic diagram showing an example of a liquid crystal display device of the present invention.
  • the liquid crystal display device 10 comprises a liquid crystal cell having a liquid crystal layer 5 and a liquid crystal cell upper electrode substrate 3 and a liquid crystal cell lower electrode substrate 6 arranged above and below the liquid crystal layer 5, and an upper polarizing plate 1 and a lower polarizing plate 8 arranged on either side of the liquid crystal cell.
  • a color filter layer may be laminated on the upper electrode substrate 3 or the lower electrode substrate 6.
  • a backlight is arranged on the rear of the liquid crystal display device 10. The light source for the backlight can be one described above in the backlight unit.
  • the upper polarizing plate 1 and the lower polarizing plate 8 each have a structure in which a polarizer is sandwiched between two polarizing plate protective films, and it is preferable that in the liquid crystal display device 10, at least one of the polarizing plates is a polarizing plate including the optical filter of the present invention.
  • the liquid crystal cell and the polarizing plate (upper polarizing plate 1 and/or lower polarizing plate 8) may be bonded together via an adhesive layer (not shown).
  • the optical filter of the present invention may also serve as the adhesive layer.
  • the liquid crystal display device 10 may be of a direct image viewing type, an image projection type, or an optical modulation type.
  • the present invention is effective for an active matrix liquid crystal display device using three-terminal or two-terminal semiconductor elements such as a thin film transistor (TFT) or a metal insulator metal (MIM).
  • TFT thin film transistor
  • MIM metal insulator metal
  • the present invention is also effective for a passive matrix liquid crystal display device such as a super twisted nematic (STN) mode, which is called time division driving.
  • STN super twisted nematic
  • the polarizing plate of the liquid crystal display device may be a normal polarizing plate (a polarizing plate not including the optical filter of the present invention) or a polarizing plate including the optical filter of the present invention
  • the pressure-sensitive adhesive layer may be a normal pressure-sensitive adhesive layer (not including the optical filter of the present invention) or a pressure-sensitive adhesive layer including the optical filter of the present invention.
  • the IPS (In Plane Switching) mode liquid crystal display device described in paragraphs 0128 to 0136 of JP 2010-102296 A is preferable as the liquid crystal display device of the present invention, except that it uses the optical filter of the present invention.
  • the polarizing plate used in the present invention includes a polarizer and at least one polarizing plate protective film.
  • the polarizing plate used in the present invention preferably has a polarizer and polarizing plate protective films on both sides of the polarizer, and preferably includes the optical filter of the present invention as a polarizing plate protective film on at least one side.
  • the polarizer may have a normal polarizing plate protective film on the side opposite to the side having the optical filter of the present invention (polarizing plate protective film of the present invention).
  • the thickness of the polarizing plate protective film is preferably 5 to 120 ⁇ m, more preferably 10 to 100 ⁇ m.
  • a thinner film is preferable because it is less likely to cause display unevenness after aging at high temperature and high humidity when incorporated into a liquid crystal display device.
  • a thicker film is preferable from the viewpoint of stable transport during film production and polarizing plate production.
  • the optical filter of the present invention also serves as a polarizing plate protective film, it is preferable that the thickness of the optical filter satisfies the above range.
  • the polarizing plate used in the present invention the performance, shape, configuration, polarizer, lamination method of the polarizer and the polarizing plate protective film, and functionalization of the polarizing plate described in paragraphs [0299] to [0309] of WO 2021/132674 can be directly applied.
  • the polarizing plate is preferably attached to the liquid crystal cell via an adhesive layer.
  • the optical filter of the present invention may also serve as the adhesive layer.
  • a normal adhesive layer can be used as the adhesive layer.
  • the adhesive layer is not particularly limited as long as it can bond the polarizing plate and the liquid crystal cell, but for example, acrylic, urethane, polyisobutylene, etc. are preferred.
  • the optical filter of the present invention also serves as a pressure-sensitive adhesive layer, the pressure-sensitive adhesive layer contains the dye, the acid group-containing resin A, and the base polymer, and further contains a crosslinking agent, a coupling agent, etc.
  • the pressure-sensitive adhesive layer preferably contains the above-mentioned base polymer in an amount of 90% by mass or more and less than 100% by mass, and more preferably 95% by mass or more and less than 100% by mass.
  • the content of the dye is as described above.
  • the thickness of the pressure-sensitive adhesive layer is not particularly limited, but is preferably, for example, 1 to 50 ⁇ m, and more preferably 3 to 30 ⁇ m.
  • the liquid crystal cell is not particularly limited, and a conventional one can be used.
  • An organic electroluminescent display device, an inorganic electroluminescent display device or a liquid crystal display device including the optical filter of the present invention preferably has a layer (hereinafter also referred to as "ultraviolet absorbing layer") on the viewer side of the optical filter of the present invention, which inhibits light absorption (ultraviolet absorbing) of compound B that forms hydrogen bonds with the acid groups contained in the resin A and generates radicals upon ultraviolet ray irradiation.
  • a layer hereinafter also referred to as "ultraviolet absorbing layer”
  • the ultraviolet absorbing layer generally contains a resin and an ultraviolet absorbing agent.
  • the ultraviolet absorbing agent is preferably one that has excellent absorption of ultraviolet rays having a wavelength of 370 nm or less and has little absorption of visible light having a wavelength of 400 nm or more from the viewpoint of good liquid crystal display properties.
  • Specific examples of ultraviolet absorbents preferably used in the present invention include hindered phenol compounds, benzophenone compounds such as hydroxybenzophenone compounds, benzotriazole compounds, salicylic acid ester compounds, cyanoacrylate compounds, and nickel complex compounds.
  • hindered phenol compound examples include 2,6-di-tert-butyl-p-cresol, pentaerythrityl-tetrakis[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate], N,N'-hexamethylenebis(3,5-di-tert-butyl-4-hydroxy-hydrocinnamide), 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, and tris-(3,5-di-tert-butyl-4-hydroxybenzyl)-isocyanurate.
  • benzotriazole-based compounds examples include 2-(2'-hydroxy-5'-methylphenyl)benzotriazole, 2,2-methylenebis(4-(1,1,3,3-tetramethylbutyl)-6-(2H-benzotriazol-2-yl)phenol), 2,4-bis(n-octylthio)-6-(4-hydroxy-3,5-di-tert-butylanilino)-1,3,5-triazine, triethylene glycol-bis[3-(3-tert-butyl-5-methyl-4-hydroxyphenyl)propionate], N,N'-hexamethylenebis(3,5-di-tert-butyl) 1,3,5-trimethyl-2,4,6-tris(3,5-di-tert-butyl-4-hydroxybenzyl)benzene, 2-(2'-hydroxy-3',5'-di-tert-butylphenyl)-5-chlorobenzotriazole, 2-(2'-hydroxy-5
  • the resin used in the ultraviolet absorbing layer may be a commonly used resin, and is not particularly limited as long as it does not deviate from the spirit of the present invention.
  • the resin include cellulose acylate resin, acrylic resin, cycloolefin resin, polyester resin, and epoxy resin.
  • the location of the ultraviolet absorbing layer is not particularly limited as long as it is on the viewer side of the optical filter of the present invention, and it can be installed at any position.
  • an ultraviolet absorbing agent to a member such as a protective film of a polarizing plate or an anti-reflection film to give it the function of an ultraviolet absorbing layer.
  • an ultraviolet absorbing agent can be added to the above-mentioned pressure-sensitive adhesive layer.
  • Example [Fabrication of a light absorbing filter] The materials used to fabricate the light absorbing filters are as follows: ⁇ Polymer (resin)> (Resin 1) Cyclohexyl methacrylate-methacrylic acid random copolymer, methacrylic acid content 40 mol %, weight average molecular weight 53,500. (Resin 2) Cyclohexyl methacrylate-methacrylic acid random copolymer, methacrylic acid content 50 mol %, weight average molecular weight 46,400. (Resin 3) Cyclohexyl methacrylate-methacrylic acid random copolymer, methacrylic acid content 60 mol %, weight average molecular weight 43,800. (Resin 4) Cyclohexyl methacrylate-methacrylic acid random copolymer, methacrylic acid content 70 mol %, weight average molecular weight 49,900.
  • Resin 1 Cyclohexyl methacrylate-
  • Resin 5 Adamantyl methacrylate-acrylic acid random copolymer, acrylic acid content: 52 mol %, weight average molecular weight: 46,300.
  • the (meth)acrylic acid moieties of Resins 1 to 5 correspond to the acid groups contained in Resin A defined in the present invention.
  • Bu represents a butyl group.
  • Leveling Agent 1 A polymer surfactant composed of the following components was used as the leveling agent 1.
  • the ratio of each component is a molar ratio
  • t-Bu means a tert-butyl group.
  • Substrate 1 Cellulose acylate film (manufactured by Fujifilm Corporation, product name: ZRD40SL)
  • Example 1 Preparation of Substrate 1 with Diffusion-Impeding Layer>
  • diffusion-preventing layer-forming liquid (resin solution)
  • the components were mixed in the composition shown below and stirred in a thermostatic bath at 50° C. for 1 hour to dissolve poly(methacrylic acid) (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., weight-average molecular weight approximately 100,000) to prepare a diffusion-preventing layer-forming liquid.
  • the resulting diffusion-impeding layer-forming solution was filtered using a filter with an absolute filtration accuracy of 5 ⁇ m (product name: Hydrophobic Fluorepore Membrane, manufactured by Millex Corporation).
  • the wavelength-selective absorption layer forming solution Ba-2 obtained was filtered using filter paper (#63, manufactured by Toyo Roshi Kaisha) with an absolute filtration accuracy of 10 ⁇ m, and further filtered using a sintered metal filter (product name: Pall Filter PMF, media code: FH025, manufactured by Pall Corporation) with an absolute filtration accuracy of 2.5 ⁇ m.
  • Light absorbing filters No. 102 to 105 of the present invention were produced in the same manner as in the production of light absorbing filter No. 101, except that in the production of light absorbing filter No. 101, resin 1 constituting the wavelength selective absorption layer was changed to an equal part by mass of a resin shown in Table 1.
  • a light absorbing filter No. r201 was prepared in the same manner as in the preparation of the light absorbing filter No. 105, except that the dye D-3, the dye B-18, and the 4-methylquinoline were removed from the wavelength selection layer forming solution in the preparation of the light absorbing filter No. 105.
  • a light absorbing filter having a gas barrier layer For light absorbing filters Nos. 101 to 105 and r201, a light absorbing filter (light absorbing filter having a gas barrier layer) was produced by laminating a gas barrier layer on the light absorbing filter as described below, and the evaluation described below was performed.
  • gas barrier layer-forming liquid resin solution
  • Kuraray Exeval AQ-4105 product name, manufactured by Kuraray Co., Ltd., modified polyvinyl alcohol, saponification degree 98 to 99 mol%
  • polyethyleneimine manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., weight average molecular weight approximately 10,000
  • the resulting gas barrier layer forming liquid was filtered using a filter with an absolute filtration accuracy of 5 ⁇ m (product name: Hydrophobic Fluorepore Membrane, manufactured by Millex Corporation).
  • the gas barrier layer-forming liquid after the above-mentioned filtration treatment was applied to the wavelength selective absorption layer side of the light absorption filter using a bar coater so that the film thickness after drying would be 0.3 ⁇ m, and dried at 130° C. for 60 seconds to prepare a light absorption filter having a gas barrier layer.
  • the light absorption filter having this gas barrier layer has a structure in which a substrate 1 (14), a diffusion-preventing layer 13, a wavelength-selective absorption layer 12, and a gas barrier layer 11 are laminated in this order.
  • Nos. 101 to 105 are light-absorbing filters of the present invention
  • No. r201 is a reference light-absorbing filter.
  • Preparation of light absorbing filters No. c202 and c203 having a gas barrier layer> A comparative light absorbing filter No. c202 having a gas barrier layer was produced in the same manner as in the production of the light absorbing filter No. 101 having a gas barrier layer, except that polyethyleneimine was not added to the gas barrier layer in the production of the light absorbing filter No. 101 having a gas barrier layer.
  • a light absorbing filter No. c203 having a gas barrier layer of a comparative example was produced in the same manner as in the production of the light absorbing filter No. 104 having a gas barrier layer, except that polyethyleneimine was not added to the gas barrier layer in the production of the light absorbing filter No. 104 having a gas barrier layer.
  • the light-absorbing filter having a gas barrier layer was cut to a size of 25 mm wide and 150 mm long, and the gas barrier layer side of the light-absorbing filter was attached to glass via an adhesive (product name: SK2057, manufactured by Soken Chemical & Engineering Co., Ltd.) having a width of 30 mm and a length of 100 mm to prepare an adhesion evaluation film.
  • the light-absorbing filter having a gas barrier layer was attached such that the size of the attachment surface between the adhesive and the light-absorbing filter having a gas barrier layer was 25 mm wide and 100 mm long, and the filter protruded from the laminate of the adhesive and glass by 25 mm wide and 50 mm long (not attached to the adhesive).
  • a 90-degree peel test was carried out at a peel speed of 300 mm/min and 25° C. according to JIS standard: JIS Z-0237 (2009).
  • a cutter was used to make a 25 mm-wide cut at the boundary between the part of the light-absorbing filter having a gas barrier layer that was attached to the adhesive and the part that was not attached to the adhesive, from the gas barrier layer side to the diffusion-preventing layer, which is the layer in front of the substrate, so that the cut did not reach the substrate.
  • the part of the light-absorbing filter having a gas barrier layer that was not attached to the glass was held, and the part of the light-absorbing filter having a gas barrier layer that was attached to the glass was peeled off 50 mm in a direction perpendicular to the glass surface toward the opposite side to the glass side, and the peel force at that time was measured with a tensile tester.
  • the average peel strength (average peel strength) from the position where the peel was removed 20 mm to the position where the peel was removed 50 mm was calculated, and the adhesion was evaluated based on this average peel strength according to the following criteria.
  • Resins 1 to 5 Resins 1 to 5 described above, respectively.
  • Polyethyleneimine Fujifilm Wako Pure Chemical Industries, Ltd., weight average molecular weight approximately 10,000
  • Poly(N-vinylamine) Poly(N-vinylamine) resin, manufactured by Mitsubishi Chemical Corporation, trade name: PVAM-0570B, weight average molecular weight 100,000 Amount added: indicates the content by mass of the resin containing a basic group in the gas barrier layer. "-": Indicates that the gas barrier layer does not contain a resin containing a basic group.
  • the results in Table 1 show that the light absorption filters No. 101 to 106 of the present invention, which have a gas barrier layer as an adjacent layer as specified in the present invention, exhibit excellent adhesion.
  • the light absorption filters No. c202 and c203 of the comparative examples do not satisfy the provisions of the present invention in that the gas barrier layer, which is an adjacent layer disposed directly on one side of the wavelength selective absorption layer, does not contain a resin containing a basic group.
  • These light absorption filters No. c202 and c203 of the comparative examples have insufficient adhesion, and peeling easily occurs at the interface between the wavelength selective absorption layer and the gas barrier layer.
  • the decolorization rate was evaluated for the light absorbing filters Nos. 101 to 106 having a gas barrier layer.
  • UV light irradiation test Under atmospheric pressure (101.33 kPa), the light absorbing filter having a gas barrier layer and the standard filter were irradiated with ultraviolet (UV) rays at an illuminance of 100 mW/cm 2 and an exposure dose of 2000 mJ/cm 2 from the gas barrier layer side (the side opposite to the substrate 1) at room temperature using an ultra-high pressure mercury lamp (manufactured by HOYA Corporation, product name: UL750).
  • UV ultraviolet
  • Decolorization rate (%) 100- (Ab( ⁇ max ) after ultraviolet irradiation/Ab( ⁇ max ) before ultraviolet irradiation) ⁇ 100
  • the decolorization rates of the light-absorbing filters Nos. 101 to 106 having the gas barrier layer calculated in this manner were all 90% or more, indicating excellent decolorization properties.
  • Leveling Agent 1 A polymer surfactant composed of the following components was used as the leveling agent 1.
  • the ratio of each component is a molar ratio
  • t-Bu means a tert-butyl group.
  • Substrate 1 Polyethylene terephthalate film (manufactured by Toray Industries, product name: Lumirror XD-510P, film thickness 50 ⁇ m)
  • the obtained light absorbing filter forming solution Ba-1 was filtered using filter paper (#63, manufactured by Toyo Roshi Co., Ltd.) with an absolute filtration accuracy of 10 ⁇ m, and further filtered using a sintered metal filter (product name: Pall Filter PMF, media code: FH025, manufactured by Pall Corporation) with an absolute filtration accuracy of 2.5 ⁇ m.
  • r201 was produced in the same manner as in the production of light absorbing filter No. 101, except that compound B and dye were not mixed and the amount of resin mixed was changed so that the mass of the entire filter did not change.
  • Nos. 101 to 112 are light absorption filters of reference examples
  • Nos. c202 to c206 are light absorption filters for comparison
  • No. r201 is a light absorption filter for reference.
  • a light absorbing filter having a gas barrier layer For light absorbing filters Nos. 101 to 112, r201, and c202 to c206, a light absorbing filter (light absorbing filter having a gas barrier layer) was produced by further laminating a gas barrier layer on the light absorbing filter as described below, and the evaluation described below was performed.
  • Substrate 3 The wavelength selective absorption layer side of the substrate-attached light absorption filter prepared above was subjected to corona treatment using a corona treatment device (product name: Corona-Plus, manufactured by VETAPHONE) under conditions of a discharge amount of 1000 W ⁇ min/m 2 and a treatment speed of 3.2 m/min, and used as the substrate 3.
  • a corona treatment device product name: Corona-Plus, manufactured by VETAPHONE
  • the resulting gas barrier layer forming liquid was filtered using a filter with an absolute filtration accuracy of 5 ⁇ m (product name: Hydrophobic Fluorepore Membrane, manufactured by Millex Corporation).
  • the gas barrier layer-forming liquid after the above-mentioned filtration treatment was applied to the corona-treated surface of the substrate 3 using a bar coater so as to give a film thickness after drying of 1.6 ⁇ m, and then dried at 120° C. for 60 seconds to produce a light-absorbing filter having a gas barrier layer.
  • the light absorption filter having this gas barrier layer has a configuration in which a substrate 1, a wavelength selective absorption layer, and a gas barrier layer are laminated in this order.
  • ⁇ Absorbance of light absorbing filter (before UV irradiation)> (1) Measurement of Absorbance Using a UV3600 spectrophotometer (product name) manufactured by Shimadzu Corporation, the absorbance in the wavelength range of 380 to 800 nm was measured at 1 nm intervals for the light absorbing filter having a gas barrier layer and the standard filter.
  • the reference filter for the light absorbing filters Nos. 101-112, c202-c206 containing Resin 1 is the light absorbing filter No. r201 modified to contain no dye and no compound B.
  • dyes B-19 and B-18, which are azo dyes represented by the above general formula (i), and comparative dyes 1 to 4 are classified as dye A, dye 7-23, dye F-1, which is an azo dye represented by the above general formula (ii), dyes E-1 and E-2, which are azo dyes represented by the above general formula (iii), dyes D-1 and D-2, which are azo dyes represented by the above general formula (iv), and comparative dye 5 are classified as dye B, and dyes G-1 and G-2, which are indoaniline dyes represented by the above general formula (v), and dye C-73 are classified as dye C.
  • UV light irradiation test Under atmospheric pressure (101.33 kPa), the light absorbing filter having a gas barrier layer and the standard filter were irradiated with ultraviolet light (UV) from the gas barrier layer side (the side opposite to the substrate 1) at an illuminance of 100 mW/ cm2 and an irradiation amount shown in Table 1A, using an ultra-high pressure mercury lamp (manufactured by HOYA Corporation, product name: UL750) at room temperature.
  • UV ultraviolet light
  • a wavelength at which the presence or absence of secondary absorption due to decomposition of the dye can be evaluated that is, a wavelength at which the dye shows almost no absorption before ultraviolet irradiation and new absorption due to decomposition of the dye is observed, a wavelength of 450 nm can be selected for evaluation of Nos.
  • ⁇ max means the wavelength at which the light-absorbing filter exhibits the highest absorbance Ab( ⁇ ) among the maximum absorption wavelengths that the light-absorbing filter has in the wavelength region of 400 to 700 nm.
  • the blending amounts of the dye and compound B refer to parts by mass relative to 100 parts by mass of the wavelength selective absorption layer.
  • Ab( ⁇ max ) means the absorbance value at the maximum absorption wavelength ⁇ max .
  • the "-" in the color erasure rate column indicates that the corresponding dye is not contained.
  • No. 112 had a high decolorization rate when irradiated with UV light, and almost no secondary absorption due to decomposition of the dye when irradiated with UV light occurred, and the decolorization properties were excellent when irradiated with ultraviolet light at room temperature.

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PCT/JP2024/014884 2023-04-19 2024-04-12 光吸収フィルタ、光学フィルタ及びその製造方法、有機エレクトロルミネッセンス表示装置、無機エレクトロルミネッセンス表示装置及び液晶表示装置 Ceased WO2024219340A1 (ja)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000347341A (ja) * 1999-03-30 2000-12-15 Fuji Photo Film Co Ltd 熱消色性着色層を有する記録材料及び熱現像感光材料
JP2001051371A (ja) * 1999-08-05 2001-02-23 Fuji Photo Film Co Ltd 消色性着色層を有する記録材料および熱現像感光材料
WO2021132674A1 (ja) * 2019-12-26 2021-07-01 富士フイルム株式会社 光吸収フィルタ、光学フィルタ、有機エレクトロルミネッセンス表示装置及び液晶表示装置
WO2022149510A1 (ja) * 2021-01-06 2022-07-14 富士フイルム株式会社 光吸収フィルタ、光学フィルタ、自発光表示装置、有機エレクトロルミネッセンス表示装置及び液晶表示装置、並びに、光学フィルタの製造方法
WO2024085172A1 (ja) * 2022-10-21 2024-04-25 富士フイルム株式会社 光吸収フィルタ、光学フィルタ及びその製造方法、有機エレクトロルミネッセンス表示装置、無機エレクトロルミネッセンス表示装置及び液晶表示装置

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000347341A (ja) * 1999-03-30 2000-12-15 Fuji Photo Film Co Ltd 熱消色性着色層を有する記録材料及び熱現像感光材料
JP2001051371A (ja) * 1999-08-05 2001-02-23 Fuji Photo Film Co Ltd 消色性着色層を有する記録材料および熱現像感光材料
WO2021132674A1 (ja) * 2019-12-26 2021-07-01 富士フイルム株式会社 光吸収フィルタ、光学フィルタ、有機エレクトロルミネッセンス表示装置及び液晶表示装置
WO2022149510A1 (ja) * 2021-01-06 2022-07-14 富士フイルム株式会社 光吸収フィルタ、光学フィルタ、自発光表示装置、有機エレクトロルミネッセンス表示装置及び液晶表示装置、並びに、光学フィルタの製造方法
WO2024085172A1 (ja) * 2022-10-21 2024-04-25 富士フイルム株式会社 光吸収フィルタ、光学フィルタ及びその製造方法、有機エレクトロルミネッセンス表示装置、無機エレクトロルミネッセンス表示装置及び液晶表示装置

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