Light absorption filter and image display device

Abstract

Provided are a light absorption filter and an image display device including the same. The light absorption filter comprises: a light absorption layer containing a resin and a dye that includes a dipyrromethene pigment with a built-in quencher; and a gas barrier layer disposed on at least one surface of the light absorption layer.

Description

Light-absorbing filter and image display device

[0001] The present invention relates to a light-absorbing filter and an image display device.

[0002] As image display devices, organic electroluminescence (OLED) display devices, inorganic electroluminescence display devices (inorganic EL display devices), liquid crystal display devices, quantum dot display devices, micro light-emitting diode (micro LED) display devices, mini light-emitting diode (mini LED) display devices, etc. are used.

[0003] In the development of image display devices, light-absorbing filters are incorporated into the optical system to suppress deterioration of visibility due to external light reflection, etc. For example, when an OLED display device is used in an ambient light environment, such as outdoors, external light is reflected from metal electrodes constituting the OLED display device, resulting in display defects such as reduced contrast. A technique for suppressing external light reflection by providing a circular polarizer is known, but this technique has been criticized for its problem of reduced brightness. A technique for suppressing external light reflection while suppressing brightness reduction by providing a light-absorbing layer capable of absorbing external light is being investigated. For example, Patent Document 1 describes a wavelength-selective absorption filter for an OLED display device, which contains four dyes each absorbing at a different wavelength so as to satisfy a specific absorbance relationship.

[0004] In addition to the influence of external light reflection, there is also a known problem of the inclusion of light (unwanted light) in wavelength ranges other than pure red (R), green (G), and blue (B) due to the wavelength of the light source, backlight, and emission spectrum characteristics, resulting in reduced color purity, color reproducibility, and the like of image display devices. For example, Patent Document 2 describes an optical filter containing a catechol-coordinated dipyrromethene boron complex compound with a specific structure. Patent Document 2 describes that the catechol-coordinated dipyrromethene boron complex compound selectively absorbs light in the wavelength range of 480 to 530 nm, is less likely to emit fluorescence that causes contrast reduction, and exhibits excellent light resistance. Furthermore, Patent Document 3 describes an optical film containing a dipyrromethene cobalt complex with a specific structure in which two dipyrromethene ligands are coordinated. Patent Document 3 describes that the dipyrromethene cobalt complex has a ΔG (a value calculated under specific conditions using the quantum chemistry calculation program Gaussian 16) of −1.0 kcal / mol or more before and after the reaction between the boron dipyrromethene of the dipyrromethene ligand and singlet oxygen, and that the dipyrromethene cobalt complex can selectively and efficiently absorb light with a wavelength of around 500 nm (external light and secondary emission from the light source of a display device) and further has excellent light resistance.

[0005] International Publication No. 2021 / 014973 Japanese Patent Application Laid-Open No. 2023-051753 Japanese Patent Application Laid-Open No. 2023-101372

[0006] The present inventors have studied light-absorbing filters that use dipyrromethene dyes, and have found that the optical filter described in Patent Document 2 and the optical film described in Patent Document 3 both have poor tailing of light absorption due to the specific structure of the dipyrromethene dye, and when applied to an image display device, there is a problem that the display light of the image display device is unnecessarily absorbed. An object of the present invention is to provide a light-absorbing filter that uses a dipyrromethene dye and has excellent tailing of absorption and excellent light resistance, and an image display device equipped with the same.

[0007] The above-mentioned problems have been solved by the following means. <1> A light-absorbing filter comprising a light-absorbing layer containing a resin and a dye including a quencher-containing dipyrromethene dye, and a gas barrier layer arranged on at least one surface of the light-absorbing layer. <2> The light-absorbing filter according to <1>, wherein the quencher-containing dipyrromethene dye is represented by the following general formula (P): In the above formula, R １ ~R ６ represents a hydrogen atom or a substituent. ７ and R ８ represents a fluorine atom. ９ represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, or an electron-donating quencher moiety. １ ~R ６ and R ９ <3> The light-absorbing filter according to <2>, wherein the electron-donating quencher moiety is a ferrocenyl group represented by the following general formula (2M), or an aryl group having at least one of an amino group, an alkoxy group, a hydroxy group, and a nitro group as a substituent: In the above formula, L represents a single bond or a divalent linking group that is not conjugated with the dipyrromethene dye in the quencher-containing dipyrromethene dye. １ｍ ~R ９ｍ each represents a hydrogen atom or a substituent. M is an atom that can constitute a metallocene compound, and represents Fe, Co, Ni, Ti, Cu, Zn, Zr, Cr, Mo, Os, Mn, Ru, Sn, Pd, Rh, V, or Pt. * represents a bonding site with the dipyrromethene dye in the quencher-incorporated dipyrromethene dye. <4> The above L is a single bond or an arylene group having 6 to 12 carbon atoms, and the above R １ｍ ~R ９ｍ <5> An image display device comprising the light-absorbing filter according to any one of <1> to <4>.

[0008] In the present invention, when there are multiple substituents or linking groups, etc. (hereinafter referred to as substituents, etc.) represented by a specific symbol or formula, or when multiple substituents, etc. are specified simultaneously, unless otherwise specified, the respective substituents, etc. may be the same or different from each other. The same applies to the specification of the number of substituents, etc. Furthermore, when multiple substituents, etc. are adjacent (especially when they are adjacent), they may be linked to each other to form a ring, unless otherwise specified. Furthermore, unless otherwise specified, rings, such as alicyclic rings, aromatic rings, and heterocyclic rings, may be further condensed to form a condensed ring. In the present invention, unless otherwise specified, the light-absorbing layer may contain one or more of the components (dyes, resins, other components, etc.) constituting the light-absorbing layer. In the present invention, the polymer may be either a chain polymerization polymer or a condensation polymerization polymer, and may be either a homopolymer or a copolymer. Furthermore, if it is a copolymer, it may be either a random polymer, a block polymer, etc. In the present invention, unless otherwise specified, the double bond may be either E-type or Z-type in the molecule, or a mixture thereof. In the present invention, the term "compound" (including complexes) refers to the compound itself, its salts, and its ions. It also includes compounds with partially modified structures, provided that the effects of the present invention are not impaired. Furthermore, compounds that are not specified as substituted or unsubstituted may have any substituent, provided that the effects of the present invention are not impaired. This also applies to substituents and linking groups. In the present invention, a numerical range expressed using "to" refers to a range that includes the numerical values ​​before and after "to" as the lower and upper limits. In the present invention, a composition encompasses not only mixtures with constant component concentrations (i.e., uniformly dispersed components), but also mixtures with component concentrations that vary within a range that does not impair the intended function. In the present invention, "having a main absorption wavelength band in the wavelength range XX to YY nm" means that the wavelength showing maximum absorption (i.e., the maximum absorption wavelength) is present in the wavelength range XX to YY nm.Therefore, as long as this maximum absorption wavelength is within the above wavelength range, the entire absorption band including this wavelength may be within the above wavelength range, or it may extend beyond the above wavelength range. Furthermore, if there are multiple maximum absorption wavelengths, it is sufficient that the maximum absorption wavelength exhibiting the greatest absorbance is within the above wavelength range. In other words, maximum absorption wavelengths other than the maximum absorption wavelength exhibiting the greatest absorbance may be located either inside or outside the above wavelength range XX to YY nm. In the present invention, the main absorption wavelength band of a dye refers to the main absorption wavelength band of the dye measured in the state of a light-absorbing filter. Specifically, in the examples described below, this is measured in the state of a light-absorbing filter with a substrate under the conditions described in the section on absorption maximum values ​​of light-absorbing filters. In the present invention, "(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, and "(meth)acryloyl" refers to either or both of acryloyl and methacryloyl.

[0009] The light-absorbing filter of the present invention uses a dipyrromethene dye and exhibits excellent absorption tail cutting and excellent light resistance. Also, the image display device of the present invention includes the light-absorbing filter that uses the above-mentioned dipyrromethene dye and exhibits excellent absorption tail cutting and excellent light resistance.

[0010] [Light-Absorption Filter] The light-absorbing filter of the present invention comprises a light-absorbing layer containing a resin and a dye (hereinafter simply referred to as "dye") including a quencher-containing dipyrromethene dye, and a gas barrier layer disposed on at least one side of the light-absorbing layer. The light-absorbing filter of the present invention, having the above-described configuration, can exhibit excellent absorption tailing and excellent light resistance, even while using a dipyrromethene dye. While the reason for this is unclear, the quencher-containing dipyrromethene dye contained in the light-absorbing layer can deactivate the excited state of the dipyrromethene dye excited by light irradiation to the ground state by the quencher moiety contained in the quencher-containing dipyrromethene dye, thereby suppressing a decrease in absorbance. Furthermore, by combining the quencher-containing dipyrromethene dye with a gas barrier layer, the filter is configured to suppress the transmission of oxygen molecules itself. As a result, the quencher moiety contained in the quencher-containing dipyrromethene dye can be prevented from being oxidized by oxygen and degraded, thereby exhibiting excellent light resistance. Furthermore, the light absorption filter of the present invention can achieve excellent light resistance by using a quencher-containing dipyrromethene dye in combination with a gas barrier layer, without using a catechol-coordinated dipyrromethene boron complex compound having a specific structure described in Patent Document 2 or a dipyrromethene cobalt complex having a specific structure in which two dipyrromethene ligands are coordinated described in Patent Document 3, and as a result, can achieve excellent light resistance as well as excellent tailing of the absorption of the dipyrromethene dye.

[0011] [Light-absorbing layer] <Dye> The light-absorbing layer contains a dye containing a quencher-containing dipyrromethene dye. In the light-absorbing filter of the present invention, the dye containing a quencher-containing dipyrromethene dye is preferably in a form dispersed (preferably dissolved) in the resin constituting the light-absorbing layer. This dispersion may be random, regular, or the like.

[0012] (Dipyrromethene Dyes with Built-in Quenchers) In the present invention, the term "dipyrromethene dyes with built-in quenchers" refers to dyes in which a quencher moiety is covalently linked to a dipyrromethene dye via a linking group. Examples of the dipyrromethene dyes with built-in quenchers include dipyrromethene dyes with built-in electron-donating quenchers, in which the quencher moiety is an electron-donating quencher moiety, and dipyrromethene dyes with built-in electron-accepting quenchers, in which the quencher moiety is an electron-accepting quencher moiety. The electron-donating quencher moiety refers to a structural moiety that donates an electron to the lower-energy-level SOMO (Singly Occupied Molecular Orbital) of two SOMOs (Singly Occupied Molecular Orbitals) of the dipyrromethene dye in an excited state, and then accepts an electron from the higher-energy-level SOMO of the dipyrromethene dye, thereby deactivating the excited dipyrromethene dye to the ground state. The electron-accepting quencher moiety refers to a structural moiety that accepts an electron from the SOMO with the higher energy level of the two SOMOs of the dipyrromethene dye in an excited state and then donates an electron to the SOMO with the lower energy level of the dipyrromethene dye, thereby deactivating the excited dipyrromethene dye to the ground state. As shown in the above mechanism, the quencher-containing dipyrromethene dye contained in the light-absorbing layer can effectively suppress the decrease in absorbance and the generation of fluorescence associated with light absorption by the dipyrromethene dye by the quencher moiety linked to the dipyrromethene dye. Therefore, the quencher moiety in the quencher-containing dipyrromethene dye is a quencher moiety that can quench the fluorescence of the dipyrromethene dye, and it is not important which part of the chemical structure of the quencher-containing dipyrromethene dye corresponds to the quencher moiety.

[0013] Examples of the electron-donating quencher moiety include a ferrocenyl group represented by the following general formula (2M), and the aryl groups described in paragraphs

[0199] to

[0212] and

[0234] to

[0287] of WO 2019 / 066043, Aurore Loudet and Kevin Burgess, Chemical Reviews, 2007, Vol. 107, No. 11, pp. 4896-4898 of pp. 4891-4932, and Hisato Sunahara et al., Journal of the American Chemical Society, 2007, Vol. 129, No. 17, Examples of the quencher moiety include the quencher moiety in the quencher compound described on pages 5597-5604, and are preferably a ferrocenyl group represented by the following general formula (2M): or at least one of an amino group, an alkoxy group, a hydroxy group, and a nitro group, or an aryl group having at least one of these as a substituent, and more preferably a ferrocenyl group represented by the following general formula (2M): Furthermore, examples of the electron-accepting quencher moiety include the quencher moiety in the quencher compound described in paragraphs

[0288] to

[0310] of WO 2019 / 066043.

[0014] A ferrocenyl group represented by general formula (2M)

[0015] In general formula (2M), L represents a single bond or a divalent linking group that is not conjugated with the dipyrromethene dye (hereinafter referred to as the "dipyrromethene dye portion") in the quencher-containing dipyrromethene dye. １ｍ ~R ９ｍ represents a hydrogen atom or a substituent. M is an atom that can constitute a metallocene compound, and represents Fe, Co, Ni, Ti, Cu, Zn, Zr, Cr, Mo, Os, Mn, Ru, Sn, Pd, Rh, V, or Pt. * represents a bonding site to the dipyrromethene dye moiety. In the present invention, when L in general formula (2M) is a single bond, the cyclopentadienyl ring (R in general formula (2M)) that is bonded to the dipyrromethene dye moiety is a cyclopentadienyl ring. １ｍ The ring having the formula (I) is not included in the conjugated structure that is conjugated with the dipyrromethene dye moiety.

[0016] The divalent linking group that can be taken as L is not particularly limited as long as it is a linking group that is not conjugated with the dipyrromethene dye moiety, and may contain the above-mentioned conjugated structure inside it or at the end of the cyclopentadiene ring in general formula (2M). Examples of the divalent linking group include an alkylene group having 1 to 20 carbon atoms, an arylene group having 6 to 20 carbon atoms, a divalent heterocyclic group obtained by removing two hydrogen atoms from a heterocycle, -CH=CH-, -CO-, -CS-, -NR- (wherein R represents a hydrogen atom or a monovalent substituent), -O-, -S-, and -SO ２ - or -N=CH-, or a divalent linking group formed by combining a plurality of these (preferably 2 to 6). Preferred are alkylene groups having 1 to 8 carbon atoms, arylene groups having 6 to 12 carbon atoms, -CH=CH-, -CO-, -NR- (wherein R is as defined above), -O-, -S-, and -SO ２ - and -N=CH- or a divalent linking group formed by combining two or more (preferably 2 to 6) groups selected from this group, and particularly preferred are alkylene groups having 1 to 4 carbon atoms, phenylene groups, -CO-, -NH-, -O- and -SO ２ - or a linking group formed by combining two or more (preferably 2 to 6) groups selected from this group. The combined divalent linking group is not particularly limited, but may be -CO-, -NH-, -O-, or -SO ２ A group containing - is preferred, and is -CO-, -NH-, -O- or -SO ２ A linking group formed by combining two or more types of -, or -CO-, -NH-, -O- and -SO ２ - is a linking group formed by combining at least one of - with an alkylene group or an arylene group. ２ Examples of the linking group formed by combining two or more types of - include -COO-, -OCO-, -CONH-, -NHCOO-, -NHCONH-, and -SO ２ -NH-, -CO-, -NH-, -O- and -SO ２Examples of the linking group formed by combining at least one of - with an alkylene group or an arylene group include groups formed by combining -CO-, -COO-, or -CONH- with an alkylene group or an arylene group. The substituent that can be taken as R is not particularly limited, and can be any of R in the general formula (P) described later. １ ~R ６ The substituents are the same as those that can be taken as the substituents.

[0017] L is a single bond, an alkylene group having 1 to 8 carbon atoms, an arylene group having 6 to 12 carbon atoms, —CH═CH—, —CO—, —NR— (wherein R is as defined above), —O—, —S—, or —SO ２ A group selected from the group consisting of - and -N=CH- or a group formed by combining two or more groups selected from this group is preferred.

[0018] L may have one or more substituents. The substituents that L may have are not particularly limited, and examples thereof include R １ ~R ６ When L has a plurality of substituents, the substituents bonded to adjacent atoms may be bonded to each other to form a ring structure.

[0019] The alkylene group that can be taken as L may be any of linear, branched, or cyclic, so long as it has 1 to 20 carbon atoms, and examples thereof include methylene, ethylene, propylene, methylethylene, methylmethylene, dimethylmethylene, 1,1-dimethylethylene, butylene, 1-methylpropylene, 2-methylpropylene, 1,2-dimethylpropylene, 1,3-dimethylpropylene, 1-methylbutylene, 2-methylbutylene, 3-methylbutylene, 4-methylbutylene, 2,4-dimethylbutylene, 1,3-dimethylbutylene, pentylene, Examples of L include hexylene, heptylene, octylene, ethane-1,1-diyl, propane-2,2-diyl, cyclopropane-1,1-diyl, cyclopropane-1,2-diyl, cyclobutane-1,1-diyl, cyclobutane-1,2-diyl, cyclopentane-1,1-diyl, cyclopentane-1,2-diyl, cyclopentane-1,3-diyl, cyclohexane-1,1-diyl, cyclohexane-1,2-diyl, cyclohexane-1,3-diyl, cyclohexane-1,4-diyl, methylcyclohexane-1,4-diyl, etc. In the alkylene group, L may contain -CO-, -CS-, -NR- (wherein R is as defined above), -O-, -S-, -SO ２ When a linking group containing at least one of - and -N=CH- is adopted, the group such as -CO- may be incorporated at any position in the alkylene group, and the number of groups incorporated is not particularly limited.

[0020] The arylene group that can be used as L is not particularly limited as long as it is a group having 6 to 20 carbon atoms, and examples thereof include R １ ~R ６ Among the aryl groups that can be taken as L, there can be mentioned groups in which one hydrogen atom has been further removed from each of the groups exemplified as the aryl group having 6 to 20 carbon atoms. The heterocyclic group that can be taken as L is not particularly limited, and examples thereof include R １ ~R ６ Examples of the heterocyclic group include groups in which one hydrogen atom has been further removed from each of the groups exemplified as the heterocyclic group that can be taken as the heterocyclic group.

[0021] In general formula (2M), the remaining partial structure excluding the linking group L corresponds to a structure (metallocene structural part) obtained by removing one hydrogen atom from a metallocene compound. In the present invention, the metallocene compound that serves as the metallocene structural part can be any known metallocene compound without any particular limitation, as long as it is a compound that conforms to the partial structure defined by general formula (2M) above (a compound in which a hydrogen atom is bonded in place of L). The metallocene structural part defined by general formula (2M) will be specifically described below.

[0022] In general formula (2M), R １ｍ ~R ９ｍ R each represents a hydrogen atom or a substituent. １ｍ ~R ９ｍ The substituents that can be used as the substituents are not particularly limited, but for example, R １ ~R ６ The substituents R can be selected from those which can be taken as R １ｍ ~R ９ｍ are each preferably a hydrogen atom, a halogen atom, an alkyl group, an acyl group, an alkoxy group, an amino group, or an amide group, more preferably a hydrogen atom, a halogen atom, an alkyl group, an acyl group, or an alkoxy group, still more preferably a hydrogen atom, a halogen atom, an alkyl group, or an acyl group, particularly preferably a hydrogen atom, a halogen atom, or an alkyl group, and most preferably a hydrogen atom.

[0023] R １ｍ ~R ９ｍ Examples of alkyl groups that can be used as R １Among the alkyl groups that can be taken as R, alkyl groups having 1 to 8 carbon atoms are preferred, and examples thereof include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, pentyl, tert-pentyl, hexyl, octyl, and 2-ethylhexyl. This alkyl group may have a halogen atom as a substituent. Examples of alkyl groups substituted with a halogen atom include chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, dibromomethyl, tribromomethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, perfluoroethyl, perfluoropropyl, and perfluorobutyl. In addition, R １ｍ In the alkyl group which can be taken as the above, at least one methylene group forming the carbon chain may be substituted with -O- or -CO-. Examples of the alkyl group in which a methylene group is substituted with -O- include alkyl groups in which a terminal methylene group is substituted, such as methoxy, ethoxy, propoxy, isopropoxy, isobutoxy, sec-butoxy, tert-butoxy, 2-methoxyethoxy, chloromethyloxy, dichloromethyloxy, trichloromethyloxy, bromomethyloxy, dibromomethyloxy, tribromomethyloxy, fluoromethyloxy, difluoromethyloxy, trifluoromethyloxy, 2,2,2-trifluoroethyloxy, perfluoroethyloxy, perfluoropropyloxy, and perfluorobutyloxy, as well as alkyl groups in which an internal methylene group of the carbon chain, such as 2-methoxyethyl, is substituted. Examples of the alkyl group in which a methylene group is substituted with —CO— include acetyl, propionyl, monochloroacetyl, dichloroacetyl, trichloroacetyl, trifluoroacetyl, propan-2-one-1-yl, and butan-2-one-1-yl.

[0024] In general formula (2M), M is an atom that can constitute a metallocene compound and represents Fe, Co, Ni, Ti, Cu, Zn, Zr, Cr, Mo, Os, Mn, Ru, Sn, Pd, Rh, V, or Pt. Among these, M is preferably Fe, Ti, Co, Ni, Zr, Ru, or Os, more preferably Fe, Ti, Ni, Ru, or Os, still more preferably Fe or Ti, and most preferably Fe.

[0025] Further, a 2-hydroxy-5-methoxy-phenyl group, a 3,4,5-trimethoxyphenyl group, a 2,4,6-trimethoxyphenyl group, a 2,6-dimethoxyphenyl group, a 6-hydroxynaphthyl group, a 4-methoxynaphthyl group, a 2,4,6-trimethylphenyl group, and a 9-phenylanthracenyl group are also preferred examples of the electron-donating quencher moiety.

[0026] On the other hand, the electron-accepting quencher moiety is preferably a structure having an electron-withdrawing substituent such as a halogen atom or a nitro group, and preferred examples thereof include a 3-nitrophenyl group, a 3,5-dinitrophenyl group, a 2-methoxy-5-nitro-phenyl group, a nitro group, and an iodine atom.

[0027] The ferrocenyl group represented by the general formula (2M) includes L, R １ｍ ~R ９ｍ and a group formed by combining the preferred ones of M and M together are preferred, and for example, L is a single bond, an alkylene group having 2 to 8 carbon atoms, an arylene group having 6 to 12 carbon atoms, -CH=CH-, -CO-, -NR- (wherein R is as defined above), -O-, -S-, -SO ２ a group selected from the group consisting of - and -N=CH- or a group formed by combining two or more groups selected from this group, and R １ｍ ~R ９ｍ Examples of the groups include a group formed by combining a hydrogen atom, a halogen atom, an alkyl group, an acyl group, or an alkoxy group as L and Fe as M. Among these, groups formed by combining a single bond or an arylene group having 6 to 12 carbon atoms as L and Fe as R are particularly preferred. １ｍ ~R ９ｍ is preferably a group formed by combining a hydrogen atom, a halogen atom, an alkyl group, an acyl group, or an alkoxy group with Fe as M; L is preferably a single bond or an arylene group having 6 to 12 carbon atoms; and R１ｍ ~R ９ｍ A group formed by combining a hydrogen atom as the group and Fe as M is more preferred.

[0028] In the above-mentioned quencher-incorporating dipyrromethene dye, the dipyrromethene dye refers to a dye in which a dipyrromethene ligand, which is a monovalent bidentate ligand, forms a complex with a typical element or a transition element. The typical element or transition element to which the dipyrromethene ligand is coordinated is not particularly limited, and examples thereof include B, Zn, Mg, Si, Sn, Rh, Pt, Pd, Mo, Mn, Pb, Cu, Ni, Co, and Fe. B, Zn, Mg, Si, Sn, Rh, Pt, Pd, Mo, Mn, Pb, Cu, Ni, and Fe are preferred, and B is more preferred. Furthermore, the typical element or transition element to which the dipyrromethene ligand is coordinated may have a ligand other than the dipyrromethene ligand, and may further include a fluorine atom, a fluorine atom, or a fluorine atom represented by the R ７ and R ８ The ligand is preferably a fluorine atom, or a ligand of a carboxylic acid, a ketone, a diketone or an acetoacetic ester, more preferably a fluorine atom.

[0029] The dipyrromethene dye containing a quencher is preferably a dipyrromethene dye containing an electron-donating quencher, and more preferably a dipyrromethene dye containing an electron-donating quencher represented by the following general formula (P).

[0030] Dipyrromethene dyes containing an electron-donating quencher represented by general formula (P)

[0031] In the above formula, R １ ~R ６ represents a hydrogen atom or a substituent. ７ and R ８ represents a fluorine atom or a ligand coordinated by an oxygen atom. ７ and R ８ is a ligand coordinated by an oxygen atom, R ７ and R ８ may be a bidentate ligand formed by linking R ９represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, or an electron-donating quencher moiety. １ ~R ９ At least one of the groups comprises an electron-donating quencher moiety.

[0032] (i) R １ ~R ６ R １ ~R ６ represents a hydrogen atom or a substituent. １ ~R ６Examples of the substituent that can be adopted as the alkyl group include a halogen atom (e.g., fluorine, chlorine, bromine), an alkyl group (preferably having 1 to 48 carbon atoms, more preferably having 1 to 24 carbon atoms, which is a linear, branched, or cyclic alkyl group, such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, dodecyl, hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-norbornyl, and 1-adamantyl), an alkenyl group (preferably having 2 to 48 carbon atoms, more preferably having 1 to 24 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, dodecyl, hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-norbornyl, and 1-adamantyl), and an alkenyl group (preferably having 2 to 48 carbon atoms, more preferably having 1 to 24 carbon atoms). alkenyl groups having 2 to 18 carbon atoms, for example, vinyl, allyl, 3-buten-1-yl), aryl groups (preferably aryl groups having 6 to 48 carbon atoms, more preferably 6 to 24 carbon atoms, for example, phenyl, naphthyl), heterocyclic groups (preferably heterocyclic groups having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, for example, 2-thienyl, 4-pyridyl, 2-furyl, 2-pyrimidinyl, 1-pyridyl, 2-benzothiazolyl, 1-imidazolyl, 1-pyrazolyl, benzotriazol-1-yl), silyl groups (preferably having 3 to 38 carbon atoms, more preferably 1 to 24 carbon atoms, for example, phenyl, naphthyl), silyl groups having 3 to 18 carbon atoms, for example, trimethylsilyl, triethylsilyl, tributylsilyl, t-butyldimethylsilyl, and t-hexyldimethylsilyl), hydroxyl groups, cyano groups, nitro groups, alkoxy groups (preferably alkoxy groups having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, for example, methoxy, ethoxy, 1-butoxy, 2-butoxy, isopropoxy, t-butoxy, dodecyloxy, cycloalkyloxy groups, for example, cyclopentyloxy and cyclohexyloxy), aryloxy groups (preferably 6 to 48 carbon atoms, More preferably, it is an aryloxy group having 6 to 24 carbon atoms, for example, phenoxy, 1-naphthoxy), a heterocyclic oxy group (preferably a heterocyclic oxy group having 1 to 32 carbon atoms, more preferably a heterocyclic oxy group having 1 to 18 carbon atoms, for example, 1-phenyltetrazole-5-oxy, 2-tetrahydropyranyloxy), a silyloxy group (preferably a silyloxy group having 1 to 32 carbon atoms, more preferably a silyloxy group having 1 to 18 carbon atoms, for example, trimethylsilyloxy, t-butyldimethylsilyloxy, diphenylmethylsilyloxy), an acyloxy group (preferably a group having 2 to 48 carbon atoms,more preferably an acyloxy group having 2 to 24 carbon atoms, for example, acetoxy, pivaloyloxy, benzoyloxy, dodecanoyloxy), an alkoxycarbonyloxy group (preferably an alkoxycarbonyloxy group having 2 to 48 carbon atoms, more preferably an alkoxycarbonyloxy group having 2 to 24 carbon atoms, for example, ethoxycarbonyloxy, t-butoxycarbonyloxy, a cycloalkyloxycarbonyloxy group, for example, cyclohexyloxycarbonyloxy), an aryloxycarbonyloxy group (preferably an aryloxycarbonyloxy group having 7 to 32 carbon atoms, more preferably an aryloxycarbonyloxy group having 7 to 24 carbon atoms, for example, phenoxycarbonyloxy),

[0033] carbamoyloxy groups (preferably carbamoyloxy groups having 1 to 48 carbon atoms, more preferably carbamoyloxy groups having 1 to 24 carbon atoms, for example, N,N-dimethylcarbamoyloxy, N-butylcarbamoyloxy, N-phenylcarbamoyloxy, N-ethyl-N-phenylcarbamoyloxy), sulfamoyloxy groups (preferably sulfamoyloxy groups having 1 to 32 carbon atoms, more preferably sulfamoyloxy groups having 1 to 24 carbon atoms, for example, N,N-diethylsulfamoyloxy, N-propylsulfamoyloxy), alkylsulfonyloxy groups (preferably alkylsulfonyloxy groups having 1 to 3 carbon atoms, for example, N,N-dimethylcarbamoyloxy, N-butylcarbamoyloxy, N-phenylcarbamoyloxy, N-ethyl-N-phenylcarbamoyloxy), alkylsulfonyloxy groups (preferably having 6 to 32 carbon atoms, more preferably having 6 to 24 carbon atoms, such as phenylsulfonyloxy), acyl groups (preferably having 1 to 48 carbon atoms, more preferably having 1 to 24 carbon atoms, such as formyl, acetyl, pivaloyl, benzoyl, tetradecanoyl, cyclohexanoyl), alkoxycarbonyl groups, an alkoxycarbonyl group (preferably an alkoxycarbonyl group having 2 to 48 carbon atoms, more preferably an alkoxycarbonyl group having 2 to 24 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, octadecyloxycarbonyl, cyclohexyloxycarbonyl, or 2,6-di-tert-butyl-4-methylcyclohexyloxycarbonyl); an aryloxycarbonyl group (preferably an aryloxycarbonyl group having 7 to 32 carbon atoms, more preferably an aryloxycarbonyl group having 7 to 24 carbon atoms, such as phenoxycarbonyl); a carbamoyl group (preferably a carbamoyl group having 1 to 48 carbon atoms, more preferably a carbamoyl group having 1 to 24 carbon atoms); yl groups, for example, carbamoyl, N,N-diethylcarbamoyl, N-ethyl-N-octylcarbamoyl, N,N-dibutylcarbamoyl, N-propylcarbamoyl, N-phenylcarbamoyl, N-methyl-N-phenylcarbamoyl, and N,N-dicyclohexylcarbamoyl; amino groups (preferably amino groups having 32 or less carbon atoms, more preferably amino groups having 24 or less carbon atoms, for example, amino, methylamino, N,N-dibutylamino, tetradecylamino, 2-ethylhexylamino, and cyclohexylamino); anilino groups (preferably having 6 to 32 carbon atoms,More preferably, it is an anilino group having 6 to 24 carbon atoms, for example, anilino, N-methylanilino), a heterocyclic amino group (preferably a heterocyclic amino group having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms, for example, 4-pyridylamino), a carbonamido group (preferably a carbonamido group having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, acetamido, benzamido, tetradecanamido, pivaloylamido, cyclohexanamido), a ureido group (preferably a ureido group having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, for example, ureido, N,N-diamino), methylureido, N-phenylureido), imido groups (preferably imido groups having 36 or less carbon atoms, more preferably 24 or less carbon atoms, for example, N-succinimido, N-phthalimido), alkoxycarbonylamino groups (preferably alkoxycarbonylamino groups having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, for example, methoxycarbonylamino, ethoxycarbonylamino, t-butoxycarbonylamino, octadecyloxycarbonylamino, cyclohexyloxycarbonylamino), aryloxycarbonylamino groups (preferably represents an aryloxycarbonylamino group having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, such as phenoxycarbonylamino), a sulfonamido group (preferably a sulfonamido group having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, such as methanesulfonamido, butanesulfonamido, benzenesulfonamido, hexadecanesulfonamido, and cyclohexanesulfonamido), a sulfamoylamino group (preferably a sulfamoylamino group having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, such as N,N-dipropylsulfa N-ethyl-N-dodecylsulfamoylamino), azo groups (preferably azo groups having 1 to 32 carbon atoms, more preferably an azo group having 1 to 24 carbon atoms, for example, phenylazo, 3-pyrazolylazo), alkylthio groups (preferably an alkylthio group having 1 to 48 carbon atoms, more preferably an alkylthio group having 1 to 24 carbon atoms, for example, methylthio, ethylthio, octylthio, cyclohexylthio), arylthio groups (preferably an arylthio group having 6 to 48 carbon atoms, more preferably an arylthio group having 6 to 24 carbon atoms, for example, phenylthio), heterocyclic thio groups (preferably having 1 to 32 carbon atoms,More preferably, it is a heterocyclic thio group having 1 to 18 carbon atoms, for example, 2-benzothiazolylthio, 2-pyridylthio, 1-phenyltetrazolylthio), an alkylsulfinyl group (preferably an alkylsulfinyl group having 1 to 32 carbon atoms, more preferably an alkylsulfinyl group having 1 to 24 carbon atoms, for example, dodecanesulfinyl), an arylsulfinyl group (preferably an arylsulfinyl group having 6 to 32 carbon atoms, more preferably an arylsulfinyl group having 6 to 24 carbon atoms, for example, phenylsulfinyl), an alkylsulfonyl group (preferably an alkylsulfonyl group having 1 to 48 carbon atoms, more preferably an alkylsulfonyl group having 1 to 24 carbon atoms, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, butylsulfonyl, isopropylsulfonyl, 2-ethylhexylsulfonyl, hexadecylsulfonyl, octylsulfonyl, cyclohexylsulfonyl), an arylsulfonyl group (preferably an alkylsulfonyl group having 6 carbon atoms, arylsulfonyl groups having from 1 to 48 carbon atoms, more preferably from 6 to 24 carbon atoms, such as phenylsulfonyl and 1-naphthylsulfonyl), sulfamoyl groups (preferably sulfamoyl groups having 32 or less carbon atoms, more preferably 24 or less carbon atoms, such as sulfamoyl, N,N-dipropylsulfamoyl, N-ethyl-N-dodecylsulfamoyl, N-ethyl-N-phenylsulfamoyl and N-cyclohexylsulfamoyl), sulfo groups, phosphonyl groups (preferably phosphonyl groups having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, such as phenoxyphosphonyl, octyloxyphosphonyl and phenylphosphonyl), and phosphinoylamino groups (preferably phosphinoylamino groups having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms, such as diethoxyphosphinoylamino and dioctyloxyphosphinoylamino). １ ~R ６ Examples of the substituent that can be adopted include the electron-donating quencher moiety in the above-mentioned quencher-containing dipyrromethene dye.

[0034] R １ ~R ６ The substituents that can be taken as R may be further substituted with a substituent. In this case, R １ ~R ６ The substituents that may be further substituted by the substituents that can be taken as R１ ~R ６ Examples of substituents that can be taken as R １ ~R ６ When the substituent that can be taken as R is substituted with two or more substituents, these two or more substituents may be the same or different. １ ~R ６ Preferred examples of the group include a hydrogen atom, a halogen atom, an alkyl group, an acyl group, an alkoxycarbonyl group, an acyloxy group, an amido group, a carbamoyl group, an aryl group, a heterocyclic group, and a nitro group.

[0035] R １ and R ２ , R ２ and R ３ , R ４ and R ５ , R ５ and R ６ may each independently bond to each other to form a 5-, 6-, or 7-membered saturated or unsaturated ring. The 5-, 6-, or 7-membered saturated or unsaturated ring formed may be further substituted with a substituent. In this case, the substituent that the 5-, 6-, or 7-membered saturated or unsaturated ring formed may further have includes the above-mentioned R １ ~R ６ When the 5-, 6-, or 7-membered saturated or unsaturated ring formed is substituted with two or more substituents, these two or more substituents may be the same or different.

[0036] (ii) R ７ and R ８ R ７ and R ８ represents a fluorine atom or a ligand coordinated by an oxygen atom. ７ and R ８ is a ligand coordinated by an oxygen atom, R ７ and R ８ may be a bidentate ligand formed by linking R ７ and R ８ As the ligand coordinated by the oxygen atom, which can be taken as R ７and R ８ In addition to bidentate ligands formed by linking R, examples of the ligand include carboxylate ion ligands such as acetato, ketone or diketone ligands such as acetonato or acetylacetonato, acetoacetic ester ligands, and catechol ligands, and the carboxylate ion ligands, ketone or diketone ligands, and acetoacetic ester ligands are preferred. The benzene ring in the catechol ligand may have a substituent, and examples of the substituents that may be included include the above-mentioned R １ ~R ６ The description of the substituents that can be taken as R ７ and R ８ are preferably all fluorine atoms.

[0037] (iii) R ９ R ９ represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, or an electron-donating quencher moiety. ９ Examples of the halogen atom, alkyl group, aryl group and heterocyclic group that can be taken as R ９ The halogen atom, alkyl group, aryl group and heterocyclic group that can be taken as R １ ~R ６ The descriptions of the halogen atom, alkyl group, aryl group, and heterocyclic group that can be taken as R can be applied to each of them. ９ Examples of the electron-donating quencher moiety that can be used as R include the electron-donating quencher moiety in the above-mentioned quencher-containing dipyrromethene dye. ９ is preferably a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group.

[0038] However, R １ ~R ９ At least one of "R" contains an electron-donating quencher moiety. １ ~R ９ "at least one of R contains an electron-donating quencher moiety" means that R １ ~R ９ At least one of R is an electron-donating quencher moiety, or R １ ~R ９is a substituent substituted with an electron-donating quencher moiety. The substitution position containing the electron-donating quencher moiety is R １ ~R ９ Any of the above is acceptable, １ ~R ６ and R ９ and R ２ , R ５ and R ９ More preferably, R ９ It is more preferable that R ７ and R ８ is a fluorine atom, the substitution position containing the electron-donating quencher moiety is １ ~R ６ and R ９ and R ２ , R ５ and R ９ More preferably, R ９ The electron-donating quencher moiety can be the same as that described for the electron-donating quencher moiety in the above-mentioned quencher-incorporating dipyrromethene dye, and is preferably a ferrocenyl group represented by the above-mentioned general formula (2M), or at least one of an amino group, an alkoxy group, a hydroxy group, and a nitro group, or an aryl group having at least one of these as a substituent, and more preferably a ferrocenyl group represented by the above-mentioned general formula (2M).

[0039] Examples of the above-mentioned quencher-containing dipyrromethene dye include the following exemplary compounds. In the following, Me represents a methyl group, and Et represents an ethyl group. However, the above-mentioned quencher-containing dipyrromethene dye is not limited to these.

[0040]

[0041]

[0042] The quencher-containing dipyrromethene dye can be synthesized by a conventional method, for example, by referring to the description in Dalton Trans., 2010, Vol. 39, pp. 9929-9935 and JP-A No. 2023-051753. The quencher-containing dipyrromethene dye has a good absorption tail, so that in the light absorption filter of the present invention, the 10% absorption width of the quencher-containing dipyrromethene dye can be, for example, less than 66%, preferably 65% ​​or less, more preferably 64% or less, and even more preferably 63% or less.

[0043] The dye preferably includes at least one of the following dyes A to D. Dye A: A dye having a main absorption wavelength band in the wavelength range of 390 to 435 nm Dye B: A dye having a main absorption wavelength band in the wavelength range of 480 to 520 nm Dye C: A dye having a main absorption wavelength band in the wavelength range of 580 to 620 nm Dye D: A dye having a main absorption wavelength band in the wavelength range of 640 to 780 nm Dye A is not particularly limited, and various dyes can be used, as long as it has a main absorption wavelength band in the wavelength range of 390 to 435 nm in the light-absorbing filter of the present invention. Dye B is not particularly limited, and various dyes can be used, as long as it has a main absorption wavelength band in the wavelength range of 480 to 520 nm in the light-absorbing filter of the present invention. Dye C is not particularly limited, and various dyes can be used, as long as it has a main absorption wavelength band in the wavelength range of 580 to 620 nm in the light-absorbing filter of the present invention. Dye D is not particularly limited, and various dyes can be used, as long as it has a main absorption wavelength band in the wavelength range of 640 to 780 nm in the light-absorbing filter of the present invention. The wavelength range in which dye A has its main absorption wavelength band is preferably 400 to 435 nm, more preferably 405 to 435 nm. The wavelength range in which dye B has its main absorption wavelength band is preferably 490 to 520 nm, more preferably 490 to 515 nm. The wavelength range in which dye C has its main absorption wavelength band is preferably 580 to 615 nm, more preferably 585 to 610 nm. The wavelength range in which dye D has its main absorption wavelength band is preferably 640 to 750 nm, more preferably 650 to 700 nm. However, at least one of dyes A to D contains the above-mentioned quencher-containing dipyrromethene dye, and in particular, it is preferable that the dye corresponding to dye B contains a quencher-containing dipyrromethene dye.

[0044] Specific examples of dye A include porphyrin-based, squaraine-based, cyanine (CY)-based, pyrrole methine-based, and indoaniline-based dyes. Preferred examples of the pyrrole methine dye include the pyrrole methine dyes represented by formula (A1) or (A2) described in paragraphs

[0022] to

[0066] of WO 2022 / 138925 and the following compound (E-42).

[0045]

[0046] The dye A preferably contains a pyrrole methine dye represented by general formula (A1) of WO 2022 / 138925, since this dye has a sharp absorption waveform in the main absorption wavelength band.

[0047] Specific examples of dye B include pyrrole methine (PM), rhodamine (RH), boron dipyrromethene (BODIPY), and squaraine (SQ) dyes. The above-mentioned quencher-containing dipyrromethene dyes are also preferred as dye B. Specific examples of dye C include tetraaza porphyrin (TAP), squaraine, and cyanine (CY) dyes. Preferred examples thereof include squaraine dyes and quencher-containing dyes represented by any one of general formulas (1) to (9) described in paragraphs

[0072] to

[0169] of WO 2021 / 221122, as well as the following compounds (C-121) and (C-122).

[0048]

[0049] Among these, the above-mentioned dyes B and C preferably contain squaraine dyes, and more preferably contain squaraine dyes represented by general formula (1) described in WO 2021 / 221122, because they have sharp absorption waveforms in the main absorption wavelength band. By using dyes B and C with sharp absorption waveforms as described above, the original color of the image of the OLED display device can be maintained at an excellent level.

[0050] Specific examples of dye D include porphyrin-based, squaraine-based, cyanine (CY)-based, and indoaniline-based dyes. Preferred examples of squaraine-based dyes include squaraine-based dyes represented by general formula (14) described in paragraphs

[0089] to

[0099] of WO 2023 / 228799. Preferred examples of indoaniline-based dyes include indoaniline-based dyes represented by general formula (v) or (va-a) described in paragraphs

[0064] to

[0072] of WO 2023 / 234353.

[0051] The total content of the dyes in the light-absorbing layer is preferably 0.1 to 50% by mass, more preferably 0.3 to 40% by mass, even more preferably 0.5 to 30% by mass, particularly preferably 0.7 to 20% by mass, and especially preferably 1.0 to 15% by mass. The total content of the quencher-containing dipyrromethene dyes in the light-absorbing layer is preferably 0.1 to 30% by mass, more preferably 0.3 to 20% by mass, even more preferably 0.5 to 15% by mass, particularly preferably 0.7 to 10% by mass, and especially preferably 1.0 to 10% by mass.

[0052] When the light-absorbing layer contains the dyes A to D, the total content of the dyes A to D in the light-absorbing layer is preferably 0.01 to 45% by mass, more preferably 0.1 to 30% by mass, and even more preferably 0.1 to 10% by mass. When the light-absorbing layer contains the dyes A to D, the content of each of the dyes A to D in the light-absorbing layer is preferably 0.01 to 45% by mass, more preferably 0.1 to 30% by mass, and even more preferably 0.1 to 10% by mass.

[0053] <Resin> The resin contained in the light-absorbing layer (hereinafter also referred to as "matrix resin") is not particularly limited as long as it can disperse (preferably dissolve) the dye and has the desired light transmittance (preferably a light transmittance of 80% or more in the visible wavelength range of 400 to 800 nm). Among these, a resin capable of suppressing external light reflection and brightness reduction is preferred. The matrix resin is preferably a low-polarity matrix resin that allows the quencher-containing dipyrromethene dye to exhibit sharper absorption. Here, low polarity preferably means that the fd value defined by the following relational formula I is 0.45 or greater. Relational formula I: fd = δd / (δd + δp + δh) In relational formula I, δd, δp, and δh represent the terms corresponding to the London dispersion force, dipole-dipole force, and hydrogen bonding force, respectively, relative to the solubility parameter δt calculated by the Hoy method. A specific calculation method is as described in paragraphs

[0131] to

[0133] of WO 2022 / 138925. That is, fd indicates the ratio of δd to the sum of δd, δp, and δh. By setting the fd value to 0.45 or more, a sharper absorption waveform is more likely to be obtained. Furthermore, when the light absorbing layer contains two or more types of matrix resins, the fd value is calculated as follows: fd=Σ(w ｉ ・fd ｉ ) where w ｉ is the mass fraction of the i-th matrix resin, fd ｉ indicates the fd value of the i-th matrix resin.

[0054] Furthermore, if the matrix resin is a resin that exhibits a certain degree of hydrophobicity, the moisture content of the light-absorbing layer can be made low, for example, 0.5% or less, which is preferable from the viewpoint of improving the light resistance of the light-absorbing filter of the present invention including the light-absorbing layer. Note that the resin may contain any conventional component in addition to the polymer. However, the fd of the matrix resin is a calculated value for the polymer that constitutes the matrix resin.

[0055] Preferred examples of the matrix resin include polystyrene resin and cyclic polyolefin resin. Typically, the fd value of polystyrene resin is 0.45 to 0.60, and the fd value of cyclic polyolefin resin is 0.45 to 0.70. In addition to these preferred resins, it is also preferable to use resin components that impart functionality to the light-absorbing layer, such as the extensible resin component and release-controlling resin component described below. That is, in the present invention, the term "matrix resin" is used to include the extensible resin component and release-controlling resin component in addition to the resins described above. It is preferable that the matrix resin contain polystyrene resin in order to sharpen the absorption waveform of the dye.

[0056] (Polystyrene Resin) The polystyrene contained in the polystyrene resin refers to a polymer containing a styrene component. The polystyrene preferably contains 50% by mass or more of the styrene component. The light-absorbing layer may contain one type of polystyrene, or two or more types. Here, the styrene component is a structural unit derived from a monomer having a styrene skeleton in its structure. In order to control the photoelastic coefficient and hygroscopicity to values ​​within a preferred range for the light-absorbing layer, the polystyrene preferably contains 70% by mass or more of the styrene component, and even more preferably 85% by mass or more. It is also preferable that the polystyrene is composed only of the styrene component. The polystyrene resin described in paragraphs

[0106] to

[0110] of WO 2023 / 228799 can be applied as is to the polystyrene resin.

[0057] The light-absorbing layer preferably contains a polyphenylene ether resin in addition to the polystyrene resin. By incorporating both polystyrene resin and polyphenylene ether resin, the toughness of the light-absorbing layer can be improved, and defects such as cracks can be suppressed even in harsh environments such as high temperatures and high humidity. Examples of the polyphenylene ether resin include Zylon S201A, S202A, and S203A (all trade names) manufactured by Asahi Kasei Corporation. Alternatively, a resin prepared by pre-mixing polystyrene resin and polyphenylene ether resin may be used. Examples of mixed resins of polystyrene resin and polyphenylene ether resin include Zylon 1002H, Zylon 1000H, Zylon 600H, Zylon 500H, Zylon 400H, Zylon 300H, and Zylon 200H (all trade names) manufactured by Asahi Kasei Corporation. When the light-absorbing layer contains a polystyrene resin and a polyphenylene ether resin, the mass ratio of the two, polystyrene resin / polyphenylene ether resin, is preferably 99 / 1 to 50 / 50, more preferably 98 / 2 to 60 / 40, and even more preferably 95 / 5 to 70 / 30. By setting the blending ratio of the polyphenylene ether resin within the above preferred range, the light-absorbing layer has sufficient toughness, and when solution-formed, the solvent can be appropriately evaporated.

[0058] (Cyclic Polyolefin Resin) The cyclic olefin compound forming the cyclic polyolefin contained in the cyclic polyolefin resin (also referred to as polycycloolefin resin) is not particularly limited as long as it has a ring structure containing a carbon-carbon double bond, and examples thereof include norbornene compounds, monocyclic olefin compounds other than norbornene compounds, cyclic conjugated diene compounds, and vinyl alicyclic hydrocarbon compounds. Examples of cyclic polyolefins include (1) polymers containing structural units derived from norbornene compounds, (2) polymers containing structural units derived from monocyclic olefin compounds other than norbornene compounds, (3) polymers containing structural units derived from cyclic conjugated diene compounds, (4) polymers containing structural units derived from vinyl alicyclic hydrocarbon compounds, and hydrogenated polymers containing structural units derived from each of the compounds (1) to (4). In the present invention, polymers containing structural units derived from norbornene compounds and polymers containing structural units derived from monocyclic olefin compounds include ring-opened polymers of each compound. As the cyclic polyolefin resin, the description of the cyclic polyolefin resin described in paragraphs

[0112] to

[0125] of WO 2023 / 228799 can be applied as is.

[0059] (Extensible Resin Component) The light-absorbing layer can contain an appropriately selected resin component that exhibits extensibility (also referred to as an extensible resin component). Specific examples include acrylonitrile-butadiene-styrene resin (ABS resin), styrene-butadiene resin (SB resin), isoprene resin, butadiene resin, polyether-urethane resin, and silicone resin. These resins may also be hydrogenated as appropriate. As the extensible resin component, it is preferable to use an ABS resin or an SB resin, and it is more preferable to use an SB resin.

[0060] The SB resin may be, for example, a commercially available product, such as TR2000, TR2003, TR2250 (all trade names, manufactured by JSR Corporation), Clearene 210M, 220M, 730V (all trade names, manufactured by Denka Company Limited), Asaflex 800S, 805, 810, 825, 830, 840 (all trade names, manufactured by Asahi Kasei Corporation), and Eporex SB2400, SB2610, SB2710 (all trade names, manufactured by Sumitomo Chemical Co., Ltd.).

[0061] When the light absorbing layer contains an extensible resin component, the content of the extensible resin component in the matrix resin is preferably 15 to 95 mass %, more preferably 20 to 50 mass %, and even more preferably 25 to 45 mass %.

[0062] As the extensible resin component, when a sample having a thickness of 30 μm and a width of 10 mm is prepared using the extensible resin component alone and the breaking elongation at 25° C. is measured in accordance with JIS 7127, the extensible resin component preferably exhibits a breaking elongation of 10% or more, more preferably 20% or more.

[0063] The weight-average molecular weight (Mw) of the polymer constituting the resin is preferably 5,000 to 500,000, more preferably 10,000 to 200,000, and even more preferably 15,000 to 150,000. In the present invention, the weight-average molecular weight of the polymer can be measured as a polystyrene-equivalent molecular weight by gel permeation chromatography (GPC). Specifically, a GPC apparatus HLC-8220 (trade name, manufactured by Tosoh Corporation) is used, tetrahydrofuran is used as the eluent, and G3000HXL + G2000HXL columns (both trade names, manufactured by Tosoh Corporation) are used, and the measurement can be performed by RI (differential refractive index) at 23°C and a flow rate of 1 mL / min.

[0064] The content of the matrix resin in the light-absorbing layer is preferably 50% by mass or more but less than 100% by mass, more preferably 60% by mass or more but less than 100% by mass, and even more preferably 65% ​​by mass or more but 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. The matrix resin may be used alone or in combination of two or more types.

[0065] <Other Components> The light absorbing layer may contain a leveling agent (surfactant), an anti-fading agent described in paragraphs

[0245] to

[0261] of WO 2021 / 014973, a matting agent described in paragraphs

[0262] to

[0264] of WO 2021 / 014973, etc. Furthermore, when the light absorbing layer uses the matrix resin described in

[0145] to

[0189] of WO 2021 / 132674 as a resin, it may contain the following association inhibitor.

[0066] (Aggregation inhibitor) The light-absorbing layer preferably contains an aggregation inhibitor to inhibit or prevent the association of dye molecules in the light-absorbing layer by interacting with the dye. The aggregation inhibitor is preferably contained as a compound that sharpens the absorption waveform of the dye contained in the light-absorbing layer and exhibits the function of improving light fastness. The aggregation inhibitor used in the present invention may be any of the aggregation inhibitors described in paragraphs

[0177] to

[0228] of WO 2022 / 138925.

[0067] When the light-absorbing layer contains an association inhibitor, the content of the association inhibitor in the light-absorbing layer is preferably 0.1 to 30% by mass, more preferably 1 to 20% by mass, and even more preferably 2 to 15% by mass. The content of the association inhibitor in the light-absorbing layer is preferably 10 to 1,000 parts by mass, more preferably 20 to 700 parts by mass, and even more preferably 30 to 500 parts by mass, relative to 100 parts by mass of the total content of the dyes.

[0068] (Leveling Agent) A leveling agent (surfactant) can be appropriately mixed into the light-absorbing layer. Commonly used compounds can be used as the leveling agent, with fluorine-containing surfactants being particularly preferred. Specific examples include the compounds described in paragraphs

[0028] to

[0056] of JP-A No. 2001-330725. Preferred examples include copolymers comprising a structural unit having a fluorine-substituted alkyl group and a structural unit derived from an alkyl (meth)acrylate ester in a copolymer represented by formula (IV) described in paragraph

[0054] of JP-A No. 2001-330725. Furthermore, commercially available products such as the Megafac F (trade name) series manufactured by DIC Corporation can also be used. The content of the leveling agent in the light-absorbing layer can be adjusted appropriately depending on the purpose.

[0069] The light absorbing layer may contain, in addition to the above components, a low-molecular-weight plasticizer, an oligomer-based plasticizer, a retardation adjuster, an ultraviolet absorber, a deterioration inhibitor, a peeling promoter, an infrared absorber, an antioxidant, a filler, a compatibilizer, and the like.

[0070] <Method for producing light-absorbing layer> The light-absorbing layer can be produced by a conventional method, such as a solution film-forming method, a melt extrusion method, or a method (coating method) of forming a coating layer on a substrate film (release film) by any method, and stretching can also be combined as appropriate. The light-absorbing layer is preferably produced by a coating method. As the solution film-forming method and melt extrusion method, the descriptions of the solution film-forming method and melt extrusion method in

[0268] to

[0274] of WO 2021 / 014973 can be applied as is.

[0071] (Coating Method) In the coating method, a solution of the material for the light absorbing layer is applied to a release film to form a coating layer. A release agent or the like may be applied in advance to the surface of the release film as needed to control adhesion to the coating layer. The coating layer can be used by laminating it to another member via an adhesive layer in a later step, and then peeling off the release film. Any adhesive can be used as the adhesive constituting the adhesive layer. The release film can be stretched as needed with the solution of the material for the light absorbing layer applied to it or with the coating layer laminated on it.

[0072] The solvent used in the solution of the material for the light-absorbing layer can be appropriately selected from the viewpoints of being able to dissolve or disperse the material for the light-absorbing layer, being able to easily form a uniform surface in the coating and drying steps, being able to ensure liquid preservation, having an appropriate saturated vapor pressure, etc.

[0073] -Addition of Dye (Pigment)- The timing of adding the dye to the material for the light absorbing layer is not particularly limited as long as it is added at the time of film formation. For example, the dye may be added at the time of synthesis of the polymer that constitutes the matrix resin, or may be mixed with the material for the light absorbing layer when preparing a coating liquid for the material for the light absorbing layer.

[0074] -Release Film- The release film used to form the light absorbing layer by a coating method or the like preferably has a film thickness of 5 to 100 μm, more preferably 10 to 75 μm, and even more preferably 15 to 55 μm. When the film thickness is equal to or greater than the above-mentioned preferable lower limit, sufficient mechanical strength is easily ensured, and defects such as curling, wrinkling, and buckling are unlikely to occur. Furthermore, when the film thickness is equal to or less than the above-mentioned preferable upper limit, when a multilayer film of the light absorbing layer and the release film is stored, for example, in the form of a long roll, the surface pressure applied to the multilayer film is easily adjusted to an appropriate range, and adhesion defects are unlikely to occur.

[0075] The surface energy of the release film is not particularly limited, but the adhesive strength between the light absorbing layer and the release film can be adjusted by adjusting the relationship between the surface energies of the material of the light absorbing layer and the coating solution and the surface energy of the surface of the release film on which the light absorbing 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.

[0076] The surface energy of the release film can be calculated using the Owens method from the contact angle values ​​of water and methylene iodide. A contact angle meter, DM901 (manufactured by Kyowa Interface Science Co., Ltd.), can be used to measure the contact angle. The surface energy of the release film on the side where the light-absorbing layer is formed is preferably 41.0 to 48.0 mN / m, and more preferably 42.0 to 48.0 mN / m. When the surface energy is equal to or greater than the preferred lower limit, the uniformity of the thickness of the light-absorbing layer can be improved, and when the surface energy is equal to or less than the preferred upper limit, the peel force between the light-absorbing layer and the release film can be easily controlled within an appropriate range.

[0077] In addition, the surface unevenness of the release film is not particularly limited, but can be adjusted according to the relationship between the surface energy, hardness, and surface unevenness of the surface of the light absorbing layer and the surface energy and hardness of the surface of the release film opposite to the side on which the light absorbing layer is formed, for example, for the purpose of preventing adhesion failure when storing the multilayer film of the light absorbing layer and the release film in a long roll form.If the surface unevenness is increased, adhesion failure tends to be suppressed, and if the surface unevenness is reduced, the surface unevenness of the light absorbing layer tends to be reduced, and the haze of the light absorbing filter tends to be reduced, and can be set appropriately.

[0078] Any material and film can be used as the release film. Specific examples of the material include polyester polymers (including polyethylene terephthalate), olefin polymers, cycloolefin polymers, (meth)acrylic polymers, cellulose polymers, and polyamide polymers. Furthermore, the release film can be subjected to a surface treatment to adjust its surface properties. For example, corona treatment, room temperature plasma treatment, saponification treatment, etc. can be performed to reduce the surface energy, and silicone treatment, fluorine treatment, olefin treatment, etc. can be performed to increase the surface energy.

[0079] -Peel Force Between Light-Absorbing Layer and Release Film- When the light-absorbing layer is formed by a coating method, the peel force between the light-absorbing layer and the release film can be controlled by adjusting the material of the light-absorbing layer, the material of the release film, the internal strain of the light-absorbing layer, etc. This peel force can be measured, for example, by a test in which the release film is peeled off in a 90° direction, and the peel force measured at a rate of 300 mm / min is preferably 0.001 to 5 N / 25 mm, more preferably 0.01 to 3 N / 25 mm, and even more preferably 0.05 to 1 N / 25 mm. If the peel force is equal to or greater than the above-mentioned preferable lower limit, peeling can be prevented except in the peeling step of the release film, and if the peel force is equal to or less than the above-mentioned preferable upper limit, peeling defects (e.g., zipping and cracking of the light-absorbing layer) can be prevented in the peeling step.

[0080] <Film Thickness of Light-Absorbing Layer> The film thickness of the light-absorbing layer is not particularly limited, but is preferably 1 to 18 μm, more preferably 1 to 12 μm, and even more preferably 1 to 8 μm. When the film thickness is equal to or less than the above-mentioned preferred upper limit, the addition of a high concentration of dye to a thin film can suppress a decrease in polarization degree due to fluorescence emitted by the dye (pigment). Furthermore, when a quencher and an anti-fading agent are contained, their effects are easily manifested. On the other hand, when the film thickness is equal to or greater than the above-mentioned preferred lower limit, it becomes easier to maintain uniformity of in-plane absorbance. In the present invention, a film thickness of 1 to 18 μm means that the thickness of the light-absorbing layer is within the range of 1 to 18 μm regardless of the location where it is measured. This also applies to film thicknesses of 1 to 12 μm and 1 to 8 μm. The film thickness can be measured using an electronic micrometer (e.g., manufactured by Anritsu Corporation).

[0081] <Absorbance of Light-Absorbing Filter> In the light-absorbing filter of the present invention, the maximum absorbance exhibited by the quencher-containing dipyrromethene dye is usually preferably 0.01 to 1, and more preferably 0.1 to 0.6. In the light-absorbing filter of the present invention, the absorbance of the quencher-containing dipyrromethene dye can be adjusted by the type and amount of the quencher-containing dipyrromethene dye added (the content in the light-absorbing layer), etc.

[0082] <Moisture Content of Light-Absorbing Layer> From the viewpoint of durability, the moisture content of the light-absorbing layer is preferably 0.5% by mass or less, and more preferably 0.3% by mass or less, regardless of the film thickness, under conditions of 25°C and a relative humidity of 80%. In this specification, the moisture content of the light-absorbing layer can be measured using a sample with a thicker film thickness as necessary. After conditioning the sample for 24 hours or more, the moisture content is measured by the Karl Fischer method using a moisture meter and a sample drying device (for example, "CA-03" and "VA-05" (both manufactured by Mitsubishi Chemical Corporation)), and the moisture content can be calculated by dividing the moisture content (g) by the sample mass (g, including the moisture content).

[0083] <Glass Transition Temperature (Tg) of Light-Absorbing Layer> The glass transition temperature of the light-absorbing layer is preferably 50 to 140°C, more preferably 60 to 130°C, and even more preferably 70 to 120°C. When the glass transition temperature is equal to or higher than the preferred lower limit, deterioration during high-temperature use can be suppressed. When the glass transition temperature is equal to or lower than the preferred upper limit, the organic solvent used in the coating liquid can be prevented from remaining in the light-absorbing layer. The glass transition temperature of the light-absorbing layer can be measured by the following method. In a differential scanning calorimeter (X-DSC7000 (manufactured by IT Measurement & Control Co., Ltd.)), 20 mg of the light-absorbing layer is placed in a measuring pan, and the pan is heated from 30°C to 120°C at a rate of 10°C / min in a nitrogen stream, maintained at this temperature for 15 minutes, and then cooled to 30°C at a rate of -20°C / min. Thereafter, the pan is heated again from 30°C to 250°C at a rate of 10°C / min, and the temperature at which the baseline begins to deviate from the low temperature side is taken as the glass transition temperature Tg. The glass transition temperature of the light absorbing layer can be adjusted by mixing two or more polymers having different glass transition temperatures, or by changing the amount of a low molecular weight compound such as an anti-fading agent added.

[0084] <Treatment of Light-Absorbing Layer> The light-absorbing layer may be subjected to a hydrophilization treatment such as glow discharge treatment, corona discharge treatment, or alkaline saponification treatment, with corona discharge treatment being preferred. In the present invention, it is preferred to laminate a gas barrier layer on the light-absorbing layer after subjecting it to a hydrophilization treatment. It is also preferred to apply the methods disclosed in JP-A-6-94915 or JP-A-6-118232.

[0085] The obtained film may be subjected to a heat treatment step, a superheated steam contact step, an organic solvent contact step, etc., as required. In addition, a surface treatment may be appropriately performed.

[0086] Furthermore, the pressure-sensitive adhesive layer may be 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. Preferably, the description of the pressure-sensitive adhesive layer in the OLED display device described below can be applied.

[0087] [Gas barrier layer] In the light-absorbing filter of the present invention, a gas barrier layer is provided on at least one side of the light-absorbing layer. The light-absorbing filter of the present invention has a gas barrier layer on at least the surface of the light-absorbing layer that will come into contact with air when the light-absorbing filter of the present invention is used, thereby making it possible to suppress a decrease in the light absorption intensity of the dye (particularly, a quencher-containing dipyrromethene dye) in the light-absorbing layer. In the light-absorbing filter of the present invention, as long as a gas barrier layer is provided at the interface of the light-absorbing layer that comes into contact with air, the gas barrier layer may be provided on only one side of the light-absorbing layer or on both sides.

[0088] The material for forming the gas barrier layer is not particularly limited, and examples thereof include organic materials such as polyvinyl alcohol and polyvinylidene chloride, organic-inorganic hybrid materials such as sol-gel materials, and SiO ２ , SiO ｘ , SiON, SiN ｘ and Al ２ O ３ Examples of suitable gas barrier layers include inorganic materials such as inorganic oxides, inorganic fluorine, and inorganic fluorine. The gas barrier layer may be a single layer or a multilayer. In the case of a multilayer, examples of suitable gas barrier layers include an inorganic dielectric multilayer film and a multilayer film in which organic and inorganic materials are alternately laminated. The method for forming the gas barrier layer is not particularly limited, and examples thereof include a conventional method, such as a casting method such as spin coating or slit coating in the case of an organic material, and a method in which a resin gas barrier film is bonded to the light absorbing layer. In addition, examples of suitable methods for forming an inorganic material include a plasma enhanced chemical vapor deposition (CVD) method, a sputtering method, and a vapor deposition method.

[0089] In particular, when the gas barrier layer contains a crystalline resin, the gas barrier layer contains a crystalline resin, has a layer thickness of 0.1 μm to 10 μm, and has an oxygen permeability of 60 cc / m ２·day·atm or less. In the gas barrier layer, 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. Examples of the crystalline resin include polyvinyl alcohol and polyvinylidene chloride, and polyvinyl alcohol is preferred from the viewpoint that the crystalline portion can effectively suppress gas permeation. The "crystalline resin-containing layer having a layer thickness of 0.1 μm to 10 μm and an oxygen permeability of the layer of 60 cc / m ２ The "gas barrier layer having a gas barrier density of 1000 psi or less per 1000 psi day atm" is the same as the gas barrier layer described in paragraphs

[0180] to

[0184] of WO 2022 / 149510, and the descriptions therein can be applied as they are.

[0090] The light-absorbing filter of the present invention may further be laminated with an optional optical film as long as the effects of the present invention are not impaired. The optional optical film is not particularly limited in terms of optical properties or material, 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. An optically isotropic film or an optically anisotropic retardation film may be used. As the optional optical film containing a cellulose ester resin, for example, Fujitac TD80UL (manufactured by Fujifilm Corporation) can be used. Examples of the optical film containing an acrylic resin include an optical film containing a (meth)acrylic resin containing a styrene-based resin as 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 as described in Japanese Patent No. 5,041,532, an optical film containing a (meth)acrylic resin having a lactone ring structure as described in Japanese Patent Laid-Open No. 2009-122664, and an optical film containing a (meth)acrylic resin having a glutaric anhydride unit as described in Japanese Patent Laid-Open No. 2009-139754. Examples of the optical film containing a cyclic olefin resin include a cyclic olefin resin film as described in paragraph

[0029] and subsequent paragraphs of Japanese Patent Laid-Open No. 2009-237376, and a cyclic olefin resin film containing an additive that reduces Rth as described in Japanese Patent No. 4,881,827 and Japanese Patent Laid-Open No. 2008-063536.

[0091] Since the light-absorbing filter of the present invention contains a quencher-containing dipyrromethene dye that is excellent in absorption tail cutting and exhibits excellent light fastness, when applied to the image display device of the present invention, the quencher-containing dipyrromethene dye in the light-absorbing layer suppresses unnecessary absorption of the display light of the image display device, and exhibits excellent light fastness while improving the transmission of the display light of the image display device. Therefore, when the light-absorbing filter of the present invention, in which the combination and contents of the dyes are adjusted so as to achieve both the suppression of external light reflection and the suppression of luminance reduction, is applied to the image display device of the present invention, the quencher-containing dipyrromethene dye can achieve both the suppression of external light reflection and the suppression of luminance reduction, and exhibits excellent light fastness while improving the transmission of the display light of the image display device.

[0092] [Image Display Device] The image display device of the present invention includes the light-absorbing filter of the present invention. The image display device of the present invention can be configured to include the light-absorbing filter of the present invention in a configuration in which the gas barrier layer is positioned closer to the external light side than the light-absorbing layer, and other configurations of commonly used image display devices can be used without any particular limitations. In particular, a configuration in which the light-absorbing filter of the present invention is included in a position that provides anti-reflection function for external light is preferred. The image display device is not particularly limited, but can be used in self-luminous display devices (self-luminous display devices) such as inorganic electroluminescent display devices (inorganic EL display devices), organic electroluminescent (OLED) display devices, micro light-emitting diode (micro LED) display devices, mini light-emitting diode (mini LED) display devices, quantum dot display devices, and liquid crystal display devices. Of these, self-luminous display devices are preferred because they can more effectively exhibit the excellent light resistance exhibited by the light-absorbing filter of the present invention by including the light-absorbing filter of the present invention. Examples of the configuration of the self-luminous display device are not particularly limited, but include, for example, a display device comprising, from the side opposite to the external light, glass, a layer including a TFT (thin film transistor), a light-emitting element, the light-absorbing filter of the present invention, and a surface film. In the present invention, "mini-LED" refers to an LED with a chip size of approximately 100 to 200 μm square, and "micro-LED" refers to an LED with a chip size of less than 100 μm square. Preferred examples of micro-LEDs include those described in International Publication No. WO 2014 / 204694. Even when the self-luminous display device is configured with the light-absorbing filter of the present invention as an anti-reflection means in place of a circular polarizer, it can maintain an excellent level of absorbance of the dye (particularly the dipyrromethene dye with a built-in quencher) contained in the light-absorbing filter of the present invention. The image display device of the present invention may be configured with an anti-reflection film in combination, as long as the effects of the present invention are not impaired.

[0093] <Adhesive Layer> In the image display device of the present invention, the light-absorbing filter of the present invention is preferably bonded to glass via an adhesive layer, and more preferably bonded to glass via an adhesive layer on the surface located opposite to external light. As the adhesive layer, the descriptions relating to the adhesive layer and the formation method in the OLED display device described in

[0296] to

[0347] of WO 2021 / 014973 can be applied as is.

[0094] The method for forming the above-mentioned adhesive layer is not particularly limited, and for example, a method of applying an adhesive composition to the light-absorbing filter of the present invention by a conventional means such as a bar coater, and then drying and curing the same; a method of first applying an adhesive composition to the surface of a release substrate, drying the same, and then transferring the adhesive layer to the light-absorbing filter of the present invention using the release substrate, and then aging and curing the same; etc. are used.The release substrate is not particularly limited, and any release substrate can be used, for example, the release film in the above-mentioned method for producing the light-absorbing filter of the present invention.In addition, the conditions for application, drying, aging and curing can also be appropriately adjusted based on conventional methods.

[0095] The present invention will be described in more detail below based on examples. The materials, amounts used, ratios, processing details, processing procedures, etc. shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the examples shown below. In the following examples, "parts" and "%" representing the composition are based on mass unless otherwise specified. In addition, λ ｍａｘ means the maximum absorption wavelength showing the maximum absorbance.

[0096] (Synthesis example)

[0097] (1) Synthesis of intermediate A-1M In a 200 mL three-neck flask, 3.3 g (12.6 mmol) of bromoferrocene (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.), 2.8 g (18.9 mmol, 1.5 eq.) of 4-formylphenylboronic acid (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.), 6.9 g (65.5 mmol, 5.2 eq.) of sodium carbonate (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.), 148 mg (0.66 mmol, 0.05 eq.) of palladium acetate (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.), 314 mg (0.66 mmol, 0.05 eq.) of 2-(dicyclohexylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.), 45 ml of tetrahydrofuran (stabilizer-free) (manufactured by FUJIFILM Wako Pure Chemical Industries, Ltd.), and H ２ 24 ml of O was added, and the mixture was refluxed and stirred under a nitrogen atmosphere for 7 hours. After cooling to room temperature, the mixture was filtered through Celite, and the organic components were extracted with ethyl acetate using a separatory funnel, and the organic layer was washed twice with water. The organic layer was dried over magnesium sulfate, suction filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (eluent: ethyl acetate + hexane), yielding 1.60 g of intermediate A-1M (yield 44%). Orange solid. １ H-NMR (solvent: deuterated chloroform, δ in ppm): 9.97 (1H, s), 7.79 (2H, d, J = 8.4Hz), 7.59 (2H, d, J = 8.4Hz), 4.74 (2H, t, J = 1.8Hz), 4.44 (2H, t, J = 1.8Hz), 4.05 (5H, s)

[0098] (2) Synthesis of Dye A-1 Into a 300 mL three-neck flask, 530 mg (1.8 mmol) of intermediate A-1M and 100 mL of methylene chloride (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were added, and then 370 mg (3.9 mmol) of 2,4-dimethylpyrrole (manufactured by Tokyo Chemical Industry Co., Ltd.) and 50 μL of trifluoroacetic acid (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were added at room temperature. After stirring at room temperature for 1 hour in the dark, 460 mg (2.0 mmol) of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ, manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) was added at room temperature and stirred for 4 hours. Thereafter, triethylamine (NEt ３3 ml (21.6 mmol) of boron trifluoride diethyl ether complex (BF) was added to the solution, and the mixture was stirred at room temperature for 10 minutes. ３ Et ２ 3 ml (23.7 mmol) of FUJIFILM Corporation (manufactured by Wako Pure Chemical Industries, Ltd.) was added, stirred for 2 hours, and then left to stand overnight. ２ 100 ml of O was added, and the organic components were extracted with chloroform using a separatory funnel, and the organic layer was washed twice with water. The organic layer was dried over magnesium sulfate and subjected to suction filtration, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (eluent: ethyl acetate + chloroform), yielding 310 mg of dye A-1 (yield 34%). A red solid. １ H-NMR (solvent: deuterated chloroform, δ in ppm): 7.65 (2H, d, J = 8.4Hz), 7.23 (2H, d, J = 8.4Hz), 6.00 (2H, s), 4.74 (2H, t, J=1.8Hz), 4.39 (2H, t, J=1.8Hz), 4.00 (5H, s), 2.57 (6H, s), 1.56 (6H, s)

[0099] [Fabrication of Light-Absorbing Filter] The materials used to fabricate the light-absorbing filter are as follows: <Matrix Resin> (Resin 1) Resin 1 was a cyclic polyolefin resin, Arton RX4500 (trade name, manufactured by JSR Corporation, norbornene-based polymer, Tg: 132°C).

[0100] <Dye> The dyes used were as follows. ｍａｘ is the λ value of each dye in the light absorption filter measured by the method described below. ｍａｘ In addition, Me represents a methyl group, and Et represents an ethyl group.

[0101] Pyrromethene 546 (manufactured by Tokyo Chemical Industry Co., Ltd., boron dipyrromethene dye, λ ｍａｘ = 501 nm) was used as dye R-1.

[0102] Exemplary compound (G-2) described in JP-A No. 2023-051753 was used as dye R-2.

[0103] Compound 1 described in Table 1 of JP-A No. 2023-101372 was used as dye R-3.

[0104] (Leveling Agent 1) A polymer surfactant composed of the following components was used as leveling agent 1. In the following structural formula, the ratio of each component is a molar ratio, and t-Bu means a tert-butyl group.

[0105] (Substrate 1) Polyethylene terephthalate film (manufactured by Toray Industries, Inc., product name: Lumirror XD-510P, film thickness 50 μm)

[0106] <Production of Light-Absorbing Filter No. 101> (1) Preparation of Light-Absorbing Layer Forming Liquid A The components were mixed in the composition shown below to prepare Light-Absorbing Layer Forming Liquid A. ------------------------------------------------ Composition of Light-Absorbing Layer Forming Liquid A------------------------------------------------ Resin 1 98.3 parts by mass Leveling agent 1 0.2 parts by mass Dye A-1 1.5 parts by mass Toluene (solvent) 660.0 parts by mass Cyclohexanone (solvent) 73.3 parts by mass------------------------------------------------

[0107] Subsequently, the obtained light-absorbing layer forming liquid A was filtered using a filter paper (#63, manufactured by Toyo Roshi Kaisha) with an absolute filtration accuracy of 10 μm, and further filtered using a sintered metal filter (FH025, manufactured by Pall Corporation) with an absolute filtration accuracy of 2.5 μm.

[0108] (2) Preparation of Light-Absorbing Layer with Substrate The filtered light-absorbing layer-forming liquid A was applied to the substrate 1 using a bar coater so that the film thickness after drying would be 2.4 μm, and the applied coating was dried at 120° C. to prepare a light-absorbing layer with substrate.

[0109] (3) Preparation of Light-Absorbing Filter No. 101 As described below, a gas barrier layer was further laminated on the light-absorbing layer in the light-absorbing layer with a substrate, to prepare Light-Absorbing Filter No. 101.

[0110] (3-1) Preparation of Substrate 3 The light absorbing layer side of the substrate-attached light absorbing layer was treated with a corona treatment device (trade name: Corona-Plus, manufactured by VETAPHONE) at a discharge rate of 1000 W min / m ２ The substrate was subjected to a corona treatment under the conditions of a treatment speed of 3.2 m / min and used as a substrate 3.

[0111] (3-2) Preparation of resin solution The components were mixed in the composition shown below and stirred in a thermostatic bath at 90°C for 1 hour to dissolve Kuraray Exeval AQ-4105 (trade name, manufactured by Kuraray Co., Ltd., modified polyvinyl alcohol, saponification degree 98-99 mol%), preparing a gas barrier layer-forming liquid. ---------------------------------------------------------------- Composition of gas barrier layer-forming liquid ---------------------------------------------------------------- Kuraray Exeval AQ-4105 (trade name, manufactured by Kuraray Co., Ltd.) 4.0 parts by mass Pure water 88.5 parts by mass Isopropyl alcohol 7.5 parts by mass ----------------------------------------------------------------

[0112] Subsequently, the resulting gas barrier layer-forming liquid was filtered using a filter with an absolute filtration accuracy of 5 μm (trade name: Hydrophobic Fluorepore Membrane, manufactured by Millex Corporation).

[0113] (3-3) Lamination of Gas Barrier Layer The gas barrier layer-forming liquid after the filtration treatment was applied to the corona-treated surface (light-absorbing layer) of the substrate 3 using a bar coater so as to give a film thickness of 1.6 μm after drying, and the coating was dried at 120° C. for 60 seconds to laminate a gas barrier layer, thereby producing Light-Absorbing Filter No. 101. This Light-Absorbing Filter No. 101 had a configuration in which the substrate 1, the light-absorbing layer, and the gas barrier layer were laminated in this order.

[0114] <Preparation of Light-Absorbing Filters No. 102, c11 to c15, and r01> Light-absorbing filters No. 102, c11 to c15 were prepared in the same manner as light-absorbing filter No. 101, except that at least one of the type and blending amount of dye, and the presence or absence of a gas barrier layer, was changed as shown in Table 1 below. The blending amount of leveling agent 1 in light-absorbing filter No. 101 was fixed, and the blending amount of resin was changed in accordance with the change in the blending amount of dye, so as to maintain the mass of the entire light-absorbing layer. Furthermore, light-absorbing filter No. r01 was prepared by fixing the blending amount of leveling agent 1 in light-absorbing filter No. 101, but not blending the amount of dye, and adjusting the blending amount of resin 1 so as to maintain the mass of the entire light-absorbing layer.

[0115] Light-absorbing filters Nos. 101 and 102 are light-absorbing filters of the present invention, light-absorbing filters Nos. c11 to c15 are comparative light-absorbing filters, and light-absorbing filter No. r01 is a reference light-absorbing filter containing no dye.

[0116] <Maximum Absorption Value and 10% Value Width of Light-Absorption Filter> The absorbance of the light-absorbing filter in the wavelength range of 380 to 780 nm was measured in 1 nm increments using a UV3150 spectrophotometer (product name) manufactured by Shimadzu Corporation. ｘ (λ) and the absorbance Ab of the light-absorbing filter containing no dye (i.e., the reference light-absorbing filter No. r01). ０ (λ), Ab ｘ (λ)-Ab ０ (λ) was calculated, and the maximum value of this absorbance difference was defined as the absorption maximum. Furthermore, at the peak showing the absorption maximum, the interval between two wavelengths at which the absorbance was 10% of the absorption maximum was defined as the 10% value width. The 10% value widths are shown in Table 1. The light resistance of each of the obtained light-absorbing filters was evaluated as follows.

[0117] <Light resistance> (Preparation of light resistance evaluation film) A TAC film (triacetyl cellulose film) containing ultraviolet (UV) absorber 1 (trade name: TINUVIN 328, manufactured by Ciba-Geiky (now Novartis Pharma), concentration relative to TAC: 0.98 phr (parts by mass relative to 100 parts by mass of TAC)) and UV absorber 2 (trade name: TINUVIN 326, manufactured by Ciba-Geiky (now Novartis Pharma), concentration relative to TAC: 0.24 phr (parts by mass relative to 100 parts by mass of TAC)) was bonded to the gas barrier layer side of light-absorbing filters Nos. 101, 102, c11, c14, and c15 via an adhesive 1 (trade name: SK2057, manufactured by Soken Chemical & Engineering Co., Ltd.) having a thickness of approximately 20 μm. Subsequently, the substrate 1 was peeled off, and glass was attached to the light absorbing layer side to which the substrate 1 had been attached via the adhesive 1, to produce light resistance evaluation films No. 101, 102, c11, c14, and c15. Also, for light absorbing filters No. c12, c13, and r01 in which a gas barrier layer was not laminated on the light absorbing layer, a TAC film containing the above UV absorber 1 and UV absorber 2 was attached to the side of the light absorbing layer where the substrate 1 was not provided, and then the substrate 1 was peeled off, and glass was attached to the light absorbing layer side to which the substrate 1 had been attached via the adhesive 1, to produce light resistance evaluation films No. c12, c13, and r01.

[0118] (Maximum absorption value of lightfastness evaluation film) Using a UV1800 spectrophotometer (trade name) manufactured by Shimadzu Corporation, the absorbance of the lightfastness evaluation film in the wavelength range of 200 to 1000 nm was measured every 1 nm. The absorbance difference between the absorbance at each wavelength of the lightfastness evaluation film and the absorbance of lightfastness evaluation film No. r01, which has the same configuration except that it does not contain a dye, was calculated, and the maximum value of this absorbance difference was defined as the maximum absorption value. (Lightfastness) The lightfastness evaluation film was irradiated with light for 68 hours using a Super Xenon Weather Meter SX75 (trade name) manufactured by Suga Test Instruments Co., Ltd. under an environment of 60 ° C. and 50% relative humidity, and the maximum absorption values ​​before and after this irradiation were measured, and the lightfastness (i.e., the retention rate of absorbance) was calculated using the following formula. [Light resistance (%)]=([maximum absorption value after 68 hours of light irradiation] / [maximum absorption value before light irradiation])×100 The results are shown in Table 1.

[0119]

[0120] (Notes for the table) Amount of dye blended: This refers to the amount of dye blended in 100 parts by mass of the light absorbing layer, and is expressed in parts by mass.

[0121] The results in Table 1 above reveal the following. When the light-absorbing layer contains dye R-1, a dipyrromethene dye that does not contain a quencher moiety, comparative light-absorbing filter No. c13, which does not have a gas barrier layer, had a lightfastness of 1%, while comparative light-absorbing filter No. c11, which has a gas barrier layer, had a lightfastness of 40%, indicating poor lightfastness in both cases. Furthermore, comparative light-absorbing filter No. c12, which does not have a gas barrier layer even when its light-absorbing layer contains dye A-1, a quencher-containing dipyrromethene dye, had a lightfastness of 89%. Furthermore, comparative light-absorbing filter No. c14 has a light-absorbing layer that contains dye R-2, a catechol-coordinated dipyrromethene boron complex compound, and comparative light-absorbing filter No. c15 has a light-absorbing layer that contains dye R-3, a dipyrromethene cobalt complex coordinated with two dipyrromethene ligands. The comparative light-absorbing filter No. c14 had a 10% value width of 68 nm, and the comparative light-absorbing filter No. c15 had a 10% value width of 66 nm, both of which were poor in absorption tail cutting. In contrast, the light-absorbing filters Nos. 101 and 102 of the present invention had a 10% value width of 60 nm or 63 nm, and light fastness of 99%, which meant that they were excellent in absorption tail cutting and light fastness.

[0122] While the present invention has been described in connection with embodiments thereof, we do not intend to limit our invention to any of the details of the description unless otherwise specified, and believe that the claims should be construed broadly without departing from the spirit and scope of the invention as set forth in the appended claims.

[0123] This application claims priority based on Japanese Patent Application No. 2024-098002, filed on June 18, 2024, the contents of which are incorporated herein by reference as part of the present specification.

Claims

1. A light-absorbing filter comprising a light-absorbing layer containing a resin and a dye including a quencher-containing dipyrromethene dye, and a gas barrier layer disposed on at least one side of the light-absorbing layer.

2. The light-absorbing filter according to claim 1, wherein the quencher-containing dipyrromethene dye is represented by the following general formula (P): In the above formula, R １ ~R ６ represents a hydrogen atom or a substituent. ７ and R ８ represents a fluorine atom. ９ represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, or an electron-donating quencher moiety. １ ~R ６ and R ９ At least one of the groups comprises an electron-donating quencher moiety.

3. The light absorption filter according to claim 2, wherein the electron-donating quencher moiety is a ferrocenyl group represented by the following general formula (2M), or is at least one of an amino group, an alkoxy group, a hydroxy group, and a nitro group, or an aryl group having at least one of these as a substituent. In the above formula, L represents a single bond or a divalent linking group that is not conjugated with the dipyrromethene dye in the quencher-containing dipyrromethene dye. １ｍ ~R ９ｍ represents a hydrogen atom or a substituent. M is an atom that can constitute a metallocene compound, and represents Fe, Co, Ni, Ti, Cu, Zn, Zr, Cr, Mo, Os, Mn, Ru, Sn, Pd, Rh, V, or Pt. * represents a bonding site with the dipyrromethene dye in the quencher-incorporated dipyrromethene dye.

4. The L is a single bond or an arylene group having 6 to 12 carbon atoms, and the R １ｍ ~R ９ｍ 4. The light absorption filter according to claim 3, wherein is a hydrogen atom, a halogen atom, an alkyl group, an acyl group, or an alkoxy group, and M is Fe.

5. An image display device comprising the light-absorbing filter according to any one of claims 1 to 4.

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