JP2005077953A - Electronic display filter - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a filter for electronic display capable of cutting unnecessary external light and improving contrast.
An electronic display filter comprising a layer containing a dipyrromethene dye having an absorption maximum at 530 to 560 nm.
[Selection] Figure 1

Description

  The present invention relates to a filter for electronic displays, and more particularly to a filter for electronic displays using a dipyrromethene dye having an absorption maximum at a specific position in order to improve contrast. Examples of electronic displays include CRT (CRT), LCD (Liquid Crystal Display), Plasma Display, Organic / Inorganic EL Display, and FED (Field Emission Display). The present invention is not limited to these as long as it displays an image.

Various filters have been studied for electronic display filters for the purpose of improving contrast, adjusting color tone, cutting near infrared rays, and electromagnetic waves. Especially for adjusting color tone and improving contrast, cut off the emission of light at a specific wavelength. Various studies have been made on absorption of external light.
For example, in order to improve the bright contrast under a fluorescent lamp, it has wavelength selective cut filters for 436 nm, 547 nm, and 612 nm corresponding to the peak wavelengths of the three primary colors of red, green, and blue of a three-wavelength fluorescent tube, and Although it is known to use a plasma display filter having absorption at around 490 nm (see Patent Document 1), such a document completely describes how to obtain a wavelength selective filter. Absent.
Japanese Patent Laid-Open No. 2003-157017

  In the present invention, a filter having an excellent contrast improving effect that selectively cuts light having a specific wavelength of outside light by using a dye and does not hinder suitable light emission inherent in a display is provided. Is an issue.

  As a result of intensive studies to solve the above problems, the present inventors have found that a dipyrromethene dye having an absorption maximum in a specific wavelength region has an excellent effect on improving the contrast of a display, and completes the present invention. It came to. That is, the gist of the present invention relates to an electronic display filter characterized by having a layer containing a dipyrromethene dye having an absorption maximum at 530 to 560 nm.

  According to the present invention, by providing a layer containing a dipyrromethene dye having an absorption maximum in a specific wavelength region such as 530 to 560 nm in a substrate, light of a specific wavelength of external light is selectively used in various electronic displays. In addition, since the suitable light emission inherent in the display is not inhibited, an electronic display filter having an excellent contrast enhancement effect in a bright place can be obtained.

  Hereinafter, embodiments of the filter for electronic display of the present invention will be described in more detail. FIG. 1 shows a state in which the electronic display filter 10 of the present invention is disposed in front of the electronic display 11 and the reflected light 13 of the external light on the surface of the electronic display is reduced without significantly disturbing the light emission 12 of the electronic display. FIG.

  FIG. 2 is a characteristic showing an emission spectrum (emission spectrum 14) of an electronic display comprising a plasma display, a three-wavelength emission fluorescent lamp F10 (emission spectrum 15), and a transmission spectrum (transmission spectrum 16) of an electronic display filter. FIG. 3 is a characteristic diagram showing an emission spectrum of an electronic display composed of a plasma display, and an emission spectrum of a three-wavelength fluorescent lamp F10. As fluorescent lamps widely used as illumination, there are a normal fluorescent lamp F6 and a three-wavelength fluorescent lamp F10 described in JIS Z8719-1996. A wavelength range fluorescent lamp F10 is positioned.

  The electronic display filter 10 according to the present invention is arranged on the front surface of the electronic display 11 as shown in FIG. Reduce. As can be seen from FIG. 1, the external light 23 travels back and forth through the electronic display filter 10. That is, the external light 23 is weakened by the electronic display filter 10 a total of two times.

  As apparent from the emission spectrum 14 shown in FIG. 2, the emission of the plasma display is relatively weak in the wavelength range of 530 nm to 560 nm, but as is apparent from the emission spectrum 15 of F10 shown in FIG. The wavelength of the green light emission peak of the three-wavelength fluorescent lamp F10 is normally close to 545 nm, and by cutting off this part of the light, it is possible to effectively remove unnecessary external light components without weakening the light emission from the plasma display. Can be cut. That is, the reflection component of the external light on the display surface can be reduced, and the black portion of the screen display can be made blacker. Thereby, the contrast of the display can be improved.

Specifically, in a filter for an electronic display, the light transmittance Y ⁴ (%) of the wavelength of the green emission peak of the electronic display (usually around 525 nm in a plasma display, but varies depending on the type of phosphor or electronic display). On the other hand, when the light transmittance Y ² (%) at the wavelength of the green emission peak of the three-wavelength region fluorescent tube is 5 or more, preferably 7 or more, more preferably 10 or more, the effect of improving the contrast is high. Furthermore, 3 emission spectrum of band fluorescent lamp F10 (JIS Z8719-1996) was luminous transmittance Y ³ that using (%) is, luminous transmittance using white emission spectrum of the electronic display Y ¹ (% 1 or more, preferably 2 or more, more preferably 3 or more, the effect of improving contrast is high.

However, it is desirable that the luminous transmittance Y ¹ (%) is 10% or more, preferably 20% or more, and more preferably 30% or more so as not to greatly reduce the luminance of electronic display light emission. The luminous transmittance is the ratio of the light beam φt transmitted through the object and the light beam φi incident on the object, described in JIS Z8105-1982, φt / φi, and the relative spectral response to the brightness sensation of the human visual system. This is the average of the transmittance in the wavelength range of 380 nm to 780 nm considering the degree (spectral luminous efficiency), and this generally correlates with the lightness indicating the relative brightness of the object, so the luminous transmittance is filtered. It is used as an index of brightness / darkness.

  In order to efficiently cut green light emission having a peak wavelength of 545 nm of the three-wavelength region-type fluorescent lamp F10 as unnecessary external light with a dye, a dye having an absorption maximum at 530 to 560 nm is necessary. If the absorption maximum is on the shorter wavelength side than 530 nm or on the longer wavelength side than 560 nm, the external light component is small in this wavelength region, so the effect of cutting off the external light is low. Since there is a green emission peak (near point G in the emission spectrum 14) and this green emission is disturbed, the effect of improving the contrast is reduced, which is not preferable.

The inventors of the present invention have a dipyrromethene dye having a main absorption wavelength at a wavelength that is the same as or close to the green emission peak wavelength of 545 nm in the three-wavelength region fluorescent lamp F10 as unnecessary external light, and a relatively narrow absorption wavelength. It is found that it has a width, and by providing a layer containing a dipyrromethene dye in a filter for electronic display, it is possible to minimize a reduction in contrast enhancement effect due to absorbing suitable light emission, and effectively We have succeeded in cutting off unnecessary external light and obtaining an excellent contrast improvement effect.
Such a dipyrromethene compound can be represented by the general formula (I).

[In the formula (I), R _{11 to} R ₁₉ are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group which may have a substituent, or an esterified group. Carboxyl group, sulfonic acid group, acyl group, acyloxy group, alkyl group optionally having substituent, alkoxy group optionally having substituent, alkylthio group optionally having substituent, substituted An alkenyl group which may have a group, an aryl group which may have a substituent, an aryloxy group which may have a substituent, an arylthio group which may have a substituent, a substituent Represents a heterocyclic group which may have, a heterocyclic oxy group which may have a substituent, a carbamoyl group which may have a substituent, and M ₁ represents a transition metal atom. ]

In the general formula (I), examples of the halogen atom represented by R _{11 to} R ₁₉ include a fluorine atom, a chlorine atom, and a bromine atom.
Examples of the amino group optionally having a substituent represented by R _{11 to} R ₁₉ include an amino group, an acylamino group optionally having a substituent, and an alkylamino group optionally having a substituent. And optionally substituted dialkylamino group, arylamino group, diarylamino group, alkylarylamino group and the like. Examples of the acylamino group which may have a substituent include an alkylcarbonylamino group which may have a substituent and an arylcarbonylamino group which may have a substituent.

Examples of the alkylamino group or dialkylamino group include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, undecyl group, dodecyl group, pentadecyl group and the like. Examples thereof include amino groups that are mono- or di-substituted with ˜20 alkyl groups.
Examples of the arylamino group or diarylamino group include an amino group that is mono- or di-substituted with an aryl group having 6 to 12 carbon atoms such as a phenyl group or a naphthyl group.
The alkylarylamino group has 1 to 20 carbon atoms such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, undecyl group, dodecyl group, pentadecyl group, etc. Examples thereof include an amino group substituted with an alkyl group and an aryl group having 6 to 12 carbon atoms such as a phenyl group and a naphthyl group.

Examples of the alkylcarbonylamino group include those having 2 to 20 carbon atoms such as an acetylamino group, an ethylcarbonylamino group, and a butylcarbonylamino group.
Examples of the arylcarbonylamino group include those having 7 to 20 carbon atoms such as a phenylcarbonylamino group, a 4-ethylphenylcarbonylamino group, and a 3-butylphenylcarbonylamino group.
As the substituent bonded to the acyl group, alkyl group and aryl group of these acylamino groups, alkylamino groups, dialkylamino groups, arylamino groups, diarylamino groups or alkylarylamino groups, an alkyl group having 1 to 10 carbon atoms , A C1-C10 alkoxy group, a hydroxyl group, a halogen atom, etc. are mentioned.

Examples of the optionally esterified carboxyl group represented by R _{11 to} R ₁₉ include a carboxyl group, an optionally substituted alkoxycarbonyl group, and an optionally substituted aryloxycarbonyl group. And an alkenyloxycarbonyl group which may have a substituent.

  Examples of the alkoxycarbonyl group include C2-C20 alkoxycarbonyl groups such as a methoxycarbonyl group, an ethoxycarbonyl group, an isopropyloxycarbonyl group, and a 2,4-dimethylbutyloxycarbonyl group. Further, an aryl group having 6 to 12 carbon atoms, an alkoxycarbonyl group having 2 to 10 carbon atoms, an alkylcarbonyl group having 2 to 10 carbon atoms, and the like may be bonded to the alkoxycarbonyl group as a substituent. Examples of those having such a substitution machine include alkyloxycarbonyl groups having 8 to 20 carbon atoms such as benzyloxycarbonyl group and phenethyloxycarbonyl group, methoxycarbonylmethoxycarbonyl group, ethoxycarbonylmethoxycarbonyl group, and n-propoxy group. An alkylcarbonylalkoxycarbonyl group having 4 to 20 carbon atoms such as an alkoxycarbonylalkoxycarbonyl group having 4 to 20 carbon atoms such as a carbonylmethoxycarbonyl group and an isopropoxycarbonylmethoxycarbonyl group, a methylcarbonylmethoxycarbonyl group and an ethylcarbonylmethoxycarbonyl group; Can be mentioned. These aralkyloxycarbonyl group, alkoxycarbonylalkoxycarbonyl group, and alkylcarbonylalkoxycarbonyl group may further have the above-described substituent.

Examples of the aryloxycarbonyl group include a phenoxycarbonyl group or a naphthyloxycarbonyl group which may be substituted with an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a hydroxyl group, a halogen atom, or the like. Examples of the alkylphenoxycarbonyl group include those having 7 to 20 carbon atoms such as 2-methylphenoxycarbonyl group and 4-t-butylphenoxycarbonyl group. Examples of the alkoxyphenoxycarbonyl group include 4-methoxyphenoxycarbonyl group. The thing of C7-20 is mentioned. These alkylphenoxycarbonyl groups and alkoxyphenoxycarbonyl groups may further have the above-described substituents.
Examples of the alkenyloxycarbonyl group include those having 3 to 20 carbon atoms such as an allyloxycarbonyl group and a 2-butenoxycarbonyl group. Examples of the substituent for the alkenyloxycarbonyl group include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a hydroxyl group, and a halogen atom.

Examples of the acyl group represented by R _{11 to} R ₁₉ include formyl group, acetyl group, ethylcarbonyl group, n-propylcarbonyl group, iso-propylcarbonyl group, n-butylcarbonyl group, iso-butylcarbonyl group, sec- One having 1 to 20 carbon atoms such as butylcarbonyl group, t-butylcarbonyl group, n-pentylcarbonyl group, iso-pentylcarbonyl group, neo-pentylcarbonyl group, 2-methylbutylcarbonyl group, benzylcarbonyl group, benzoyl group Is mentioned. Examples of the substituent for the acyl group include a halogen atom, a nitro group, a hydroxyl group, a cyano group, an alkoxy group, and an aryloxy group. Examples of the acyl group substituted with a halogen atom include a chlorobenzylcarbonyl group. Examples of the acyl group substituted with a nitro group include a nitrobenzylcarbonyl group. Examples of the acyl group substituted with a hydroxyl group include a hydroxybenzylcarbonyl group and a hydroxy group. Examples of the acyl group substituted with a cyano group include a cyanobenzylcarbonyl group and a cyanopentylcarbonyl group. Examples of the acyl group substituted with an alkoxy group include a methoxybenzylcarbonyl group and the like. Examples of the acyl group substituted with an oxy group include a phenoxybenzylcarbonyl group.
Examples of the acyl group of the acyloxy group represented by R _{11 to} R ₁₉ include the same as those described above.

Examples of the alkyl group represented by R _{11 to} R ₁₉ include methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, t-butyl group, n-pentyl group, iso-pentyl group, 2-methylbutyl group, 1-methylbutyl group, neo-pentyl group, 1,2-dimethylpropyl group, 1,1-dimethylpropyl group, cyclo-pentyl group, n-hexyl group 4-methylpentyl group, 3-methylpentyl group, 2-methylpentyl group, 1-methylpentyl group, 3,3-dimethylbutyl group, 2,3-dimethylbutyl group, 1,3-dimethylbutyl group, 2 , 2-dimethylbutyl group, 1,2-dimethylbutyl group, 1,1-dimethylbutyl group, 3-ethylbutyl group, 2-ethylbutyl group, 1-ethylbutyl group, 1,2,2-trimethylbutyl group, 1, 1,2-trimethylbutyl group, 1-ethyl-2-methylpropyl group, cyclo-hexyl group, n-heptyl group, 2-methylhexyl group, 3 -Methylhexyl group, 4-methylhexyl group, 5-methylhexyl group, 2,4-dimethylpentyl group, n-octyl group, 2-ethylhexyl group, 2,5-dimethylhexyl group, 2,5,5-trimethyl Pentyl group, 2,4-dimethylhexyl group, 2,2,4-trimethylpentyl group, n-octyl group, 3,5,5-trimethylhexyl group, n-nonyl group, n-decyl group, 4-ethyloctyl Group, 4-ethyl-4,5-methylhexyl group, n-undecyl group, n-dodecyl group, 1,3,5,7-tetraethyloctyl group, 4-butyloctyl group, 6,6-diethyloctyl group, n-tridecyl group, 6-methyl-4-butyloctyl group, n-tetradecyl group, n-pentadecyl group, 3,5-dimethylheptyl group, 2,6-dimethylheptyl group, 2,4-dimethylheptyl group, 2 , 2,5,5-Tetramethylhexyl group, 1-cyclo-pentyl-2,2-dimethylpropyl group, 1-cyclo-hexyl-2,2-dimethylpropyl group Examples thereof include straight-chain, branched-chain or cyclic ones having 1 to 20 carbon atoms.

Examples of the substituent for the alkyl group include a halogen atom, an alkoxy group having 1 to 10 carbon atoms, an aryl group, a hydroxyl group, and a cyano group.
As a haloalkyl group, C1-C20 haloalkyl groups, such as a chloromethyl group, a dichloromethyl group, a fluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, a nonafluorobutyl group, are mentioned.
Examples of the alkoxyalkyl group include C2-C20 alkoxyalkyl groups such as a methoxyethyl group, an ethoxyethyl group, an iso-propyloxyethyl group, a 3-methoxypropyl group, and a 2-methoxybutyl group.

  Examples of the aralkyl group include a benzyl group and a naphthylmethyl group. Examples of the substituent for the aralkyl group include a nitro group, a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a halogen atom, and the like. Examples of the aralkyl group having a substituent include nitrobenzyl group, cyanobenzyl group, hydroxybenzyl group, methylbenzyl group, dimethylbenzyl group, trimethylbenzyl group, dichlorobenzyl group, methoxybenzyl group, ethoxybenzyl group, and trifluoromethyl. Examples thereof include those having 7 to 20 carbon atoms such as benzyl group, naphthylmethyl group, nitronaphthylmethyl group, cyanonaphthylmethyl group, hydroxynaphthylmethyl group, methylnaphthylmethyl group, trifluoromethylnaphthylmethyl group and the like.

Examples of the hydroxyalkyl group include those having 1 to 20 carbon atoms such as a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, and a hydroxybutyl group.
Examples of the cyanoalkyl group include those having 2 to 20 carbon atoms such as a cyanomethyl group, a cyanoethyl group, a cyanopropyl group, and a cyanobutyl group.

Examples of the alkoxy group represented by R _{11 to} R ₁₉ include methoxy group, ethoxy group, n-propoxy group, iso-propoxy group, n-butoxy group, iso-butoxy group, sec-butoxy group, t-butoxy group, Examples thereof include linear or branched alkoxy groups having 1 to 20 carbon atoms such as n-pentoxy group, iso-pentoxy group, neo-pentoxy group, n-hexyloxy group, n-dodecyloxy group, and the like. Examples of the substituent include an alkoxy group having 1 to 10 carbon atoms, a halogen atom, and an aryl group. Examples of the alkoxyalkoxy group include those having 2 to 20 carbon atoms such as a methoxyethoxy group, an ethoxyethoxy group, a 3-methoxypropyloxy group, and a 3- (iso-propyloxy) propyloxy group. Examples of the haloalkoxy group include those having 1 to 20 carbon atoms such as a trifluoromethoxy group. Examples of the aralkyloxy group include those having 7 to 20 carbon atoms such as a benzyloxy group.

Examples of the alkylthio group represented by R _{11 to} R ₁₉ include methylthio group, ethylthio group, n-propylthio group, iso-propylthio group, n-butylthio group, iso-butylthio group, sec-butylthio group, t-butylthio group, n-pentylthio, iso-pentylthio, 2-methylbutylthio, 1-methylbutylthio, neo-pentylthio, 1,2-dimethylpropylthio, 1,1-dimethylpropylthio, etc. The alkylthio group of 1-20 is mentioned, A halogen atom, an aryl group, etc. are mentioned as a substituent of an alkylthio group. Examples of the haloalkylthio group include a trifluoromethylthio group, and examples of the aralkylthio group include a benzylthio group.

Examples of the alkenyl group represented by R _{11 to} R ₁₉ include vinyl group, propenyl group, 1-butenyl group, iso-butenyl group, 1-pentenyl group, 2-pentenyl group, 2-methyl-1-butenyl group, 3 Carbon number of 2-methyl-1-butenyl group, 2-methyl-2-butenyl group, 2,2-dicyanovinyl group, 2-cyano-2-methylcarboxyl vinyl group, 2-cyano-2-methylsulfonvinyl group, etc. 2-20 alkenyl groups are mentioned.

Examples of the aryl group represented by R _{11 to} R ₁₉ include a phenyl group and a naphthyl group. As the substituent of the aryl group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkyl group, and an aryl Examples thereof include an amino group which may be 1 or 2 substituted with a substituent consisting of a group. Examples of the aryl group having a substituent include a nitrophenyl group, a nitronaphthyl group, a cyanophenyl group, a cyanonaphthyl group, a hydroxyphenyl group, a hydroxynaphthyl group, a 2-methylphenyl group, a 4-methylphenyl group, and a dimethylphenyl group. , Trimethylphenyl group, 4-i-propylphenyl group, 4-t-butylphenyl group, methylnaphthyl group, 2-methoxyphenyl group, ethoxyphenyl group, dichlorophenyl group, trifluoromethylphenyl group, trifluoromethylnaphthyl group, Examples thereof include those having 6 to 20 carbon atoms such as N, N-dimethylaminophenyl group.

Examples of the aryl group of the aryloxy group represented by R _{11 to} R ₁₉ include the same aryl groups as those described above.
Examples of the aryl group of the arylthio group represented by R _{11 to} R ₁₉ include the same aryl groups as those described above.

Examples of the heterocyclic group represented by R _{11 to} R ₁₉ include a C 4-20 heterocyclic ring containing an oxygen atom, a nitrogen atom or a sulfur atom as a hetero atom. Specific examples include pyrrolyl group, thienyl group, furanyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, imidazolyl group, benzoxazolyl group, benzothiazolyl group, benzoimidazolyl group, benzofuranyl group, and indolyl group. Examples of these substituents include a halogen atom, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a hydroxyl group.

Examples of the heterocyclic group of the heterocyclic oxy group represented by R _{11 to} R ₁₉ include the same heterocyclic groups as those described above.

The carbamoyl group optionally having substituents represented by R _{11 to} R ₁₉ is selected from the group consisting of an optionally substituted alkyl group and an optionally substituted aryl group. An aminocarbonyl group which may be substituted by 1 or 2 substituents may be mentioned.
Examples of the aminocarbonyl group include alkylaminocarbonyl groups having 2 to 20 carbon atoms such as a methylaminocarbonyl group, an ethylaminocarbonyl group, an n-propylaminocarbonyl group, an n-butylaminocarbonyl group, and an n-hexylaminocarbonyl group; A dialkylaminocarbonyl group having 3 to 20 carbon atoms such as a dimethylaminocarbonyl group, a diethylaminocarbonyl group, a di-n-propylaminocarbonyl group, a di-n-butylaminocarbonyl group, an N-methyl-N-cyclohexylaminocarbonyl group; Arylaminocarbonyl groups having 7 to 20 carbon atoms such as phenylaminocarbonyl group, 4-methylphenylaminocarbonyl group, 2-methoxyphenylaminocarbonyl group, 4-n-propylphenylaminocarbonyl group; hydroxyethylaminocarbonyl group, 2 -Hydroxypropyl C2-C20 mono (hydroxyalkyl) aminocarbonyl group such as aminocarbonyl group and 3-hydroxypropylaminocarbonyl group; di (hydroxyethyl) aminocarbonyl group, di (2-hydroxypropyl) aminocarbonyl group, di ( C3-C20 di (hydroxyalkyl) aminocarbonyl group such as 3-hydroxypropyl) aminocarbonyl group; methoxymethylaminocarbonyl group, methoxyethylaminocarbonyl group, ethoxymethylaminocarbonyl group, ethoxyethylaminocarbonyl group, C1-C20 mono (alkoxyalkyl) aminocarbonyl group such as xylethylaminocarbonyl group; di (methoxyethyl) aminocarbonyl group, di (ethoxymethyl) aminocarbonyl group, di (ethoxyethyl) aminocarbo Group, di (propoxyethyl) di (alkoxyalkyl) aminocarbonyl group having 5 to 20 carbon atoms such as amino group and the like.

R _{11 to} R ₁₉ are each preferably a hydrogen atom, an alkyl group which may have a substituent, and an aryl group which may have a substituent. Among them, R _{11 to} R ₁₄ and R _{16 to} R ₁₉ are a hydrogen atom and an alkyl group which may have a substituent, respectively, and R ₁₅ is an aryl group which may have a substituent. A combination is preferable, and R _{11 to} R ₁₃ are each a linear or branched alkyl group which may have a hydrogen atom or a substituent, and R ₁₄ and R _{16 to} R are particularly preferable. _This is a combination in which ₁₉ is a hydrogen atom and R ₁₅ is an aryl group which may have a substituent.

The transition metal atom represented by M ₁ may be any metal atom generally capable of forming a chelate compound with a pyromethene compound. Group 3 (Group IIIa), Group 4 (Group IVa), Group 5 (Group Va) ), Group 6 (Group VIa), Group 7 (Group VIIa), Group 8, Group 9, Group 10 (VIII), Group 11 (Group Ib), Group 12 (Group IIb), preferably Among them, atoms of Group 8 to 12 are preferable, and nickel, cobalt, iron, ruthenium, rhodium, palladium, copper, osmium, iridium, platinum, and zinc are preferable, and cobalt is more preferable.
Typical examples of the dipyrromethene dye represented by the general formula (I) are shown below.

  The dipyrromethene dye represented by the general formula (I) is, for example, Aust. J. Chem., 11, 1835-45 (1965), Heteroatom Chemistry, Vol. 1, 5, 389 (1990), USP-4 , 774, 339, USP-5, 433, 896, etc., or in accordance with them, pyrrole can be condensed and subsequently formed into a metal chelate.

  The filter for electronic displays of this invention has a layer containing the dipyrromethene dye represented by general formula (I). The layer containing the dipyrromethene dye represented by the general formula (I) is prepared by injection molding, T-die molding, calendar molding or resin containing a dipyrromethene dye obtained by directly dissolving or dispersing in various resins. Molded and formed into a film using a molding technique such as compression molding, and laminated with another transparent substrate as necessary, or dyed to a resin sheet or film constituting the transparent substrate, or a resin sheet or film By coating with a transparent substrate formed on a film or sheet, or by applying a coating solution containing a dipyrromethene dye of the general formula (I) Among these, a method of applying a coating liquid on a transparent substrate is preferable.

  The material of the transparent substrate is not particularly limited as long as it is substantially transparent and does not absorb and diffuse significantly. Specific examples include glass, polyolefin resin, amorphous polyolefin resin, polyester resin, polycarbonate resin, poly (meth) acrylate resin, polystyrene, polyvinyl chloride, polyvinyl acetate, polyarylate resin, polyether sun. Phon resin etc. can be mentioned. Among these, amorphous polyolefin resin, polyester resin, polycarbonate resin, poly (meth) acrylic ester resin, polyarylate resin, polyether sunphone resin and the like are particularly preferable. The above-mentioned resins can be blended with generally known additives, heat aging inhibitors, lubricants, antistatic agents and the like. The resin is molded into a film or sheet (plate) using a known method such as injection molding, T-die molding, calendar molding or compression molding, or a method of melting and casting in an organic solvent. The thickness is preferably in the range of 10 μm to 5 mm depending on the purpose. The base material constituting such a transparent substrate may be unstretched or stretched. Moreover, you may laminate | stack with another base material. Further, the transparent substrate may be subjected to surface treatment by a conventionally known method such as corona discharge treatment, flame treatment, plasma treatment, glow discharge treatment, rough surface treatment, chemical treatment, or coating with an anchor coating agent or a primer. good.

  The coating solution is a method of dissolving the dipyrromethene dye of the general formula (I) in an organic solvent together with a binder, or a dipyrromethene dye atomized to a particle size of 0.1 to 3 μm using a dispersant as necessary. And prepared by a method of dispersing in a solvent. At this time, the content of the dipyrromethene dye, the binder and the dispersant dissolved or dispersed in the solvent is usually 0.5 to 50% by weight, and the dipyrromethene dye, binder and dispersant are dipyrromethene dyes. The occupying ratio is usually 0.05 to 50% by weight, preferably 0.1 to 20% by weight.

  Examples of the dispersant used as necessary include polyvinyl butyral resin, phenoxy resin, rosin-modified phenol resin, petroleum resin, cured rosin, rosin ester, maleated rosin, and polyurethane resin. The amount used is usually 0.5 to 150 times by weight, preferably 0.5 to 20 times by weight with respect to the dipyrromethene dye.

  Binders used include acrylate resins such as polymethyl methacrylate resin and polyethyl acrylate resin, polycarbonate resin, ethylene-vinyl alcohol copolymer resin, ethylene-vinyl acetate copolymer resin, ABS resin, polyester resin, vinyl chloride resin , Polyvinyl butyral resin, PVPA, polystyrene resin, phenol resin, phenoxy resin, polysulfone, nylon, cellulose resin, cellulose acetate resin and the like. The amount used is usually 10 to 500 times by weight, preferably 50 to 350 times by weight with respect to the dipyrromethene dye.

  Coating of the coating liquid containing the dipyrromethene dye of the general formula (I) includes dipping method, flow coating method, spray method, bar coating method, gravure coating method, roll coating method, blade coating method, air knife coating method, etc. Coating is performed by a known coating method. At this time, coating is performed so that the film thickness is usually 0.1 to 30 μm, preferably 0.5 to 10 μm.

  The electronic display filter of the present invention can contain a compound having an absorption maximum at 570 to 605 nm in order to further improve color purity and contrast. In particular, in a plasma display panel (PDP), unnecessary light in the wavelength region of 570 to 605 nm due to neon emission is strong due to its structure, and therefore a PDP filter must contain a compound having an absorption maximum at 570 to 605 nm. Examples of the compound having an absorption maximum at 570 to 605 nm are represented by a tetraazaporphyrin compound represented by the general formula (II), a squarylium compound represented by the general formula (III), and a general formula (IV). And cyanine dyes.

[In formula (II), R ₂₁ To R ₂₈ each independently represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group which may have a substituent alkyl group, alkoxy group which may have a substituent, An aryl group which may have a substituent, an aryloxy group which may have a substituent, an alkylamino group which may have a substituent, a dialkylamino group which may have a substituent , An optionally substituted alkylthio group, or an optionally substituted arylthio group, R ₂₁ and R ₂₂ , R ₂₃ and R ₂₄ , R ₂₅ and R ₂₆ , R ₂₇ And R ₂₈ may be linked to each other to form an aliphatic carbocycle. M ₂ represents two hydrogen atoms, a divalent metal atom, a trivalent monosubstituted metal atom, a tetravalent disubstituted metal atom or an oxymetal atom. ]

  In the general formula (II), examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, Straight chain having 1 to 20 carbon atoms such as hexyl group, heptyl group, octyl group, decyl group, undecyl group, dodecyl group, tridecyl group, pentadecyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group Examples of the alkoxy group include, for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, and a decyloxy group. , Undecyloxy group, dodecyloxy group, tridecyloxy group, pen Examples thereof include linear or branched ones having 1 to 20 carbon atoms such as a decyloxy group, and examples of the aryl group include a hydrocarbon aryl group such as a phenyl group and a naphthyl group, or a thienyl group and a furyl group. Or a heterocyclic aryl group such as a pyridyl group. Examples of the aryloxy group include a hydrocarbon aryloxy group such as a phenoxy group and a naphthyloxy group, or a thienyloxy group, a furyloxy group, and a pyridyloxy group. A heterocyclic aryloxy group such as a group, and the alkylamino group or dialkylamino group includes a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a decyl group. Straight chain or branched chain having 1 to 20 carbon atoms such as undecyl group, dodecyl group, tridecyl group, pentadecyl group, etc. Examples of the alkylthio group include, for example, methylthio group, ethylthio group, propylthio group, butylthio group, pentylthio group, hexylthio group, heptylthio group, octylthio group, decylthio group, undecylthio group, and the like. C1-C20 linear or branched groups, such as a group, a dodecylthio group, a tridecylthio group, a pentadecylthio group, etc. are mentioned, As an arylthio group, a phenylthio group and a naphthylthio group are mentioned, for example.

  Examples of the substituent for the alkyl group, alkoxy group, aryl group, aryloxy group, alkylamino group, dialkylamino group, alkylthio group, and arylthio group include a methyl group, an ethyl group, a propyl group, a butyl group, C1-C10 alkyl groups such as pentyl group, hexyl group, heptyl group, octyl group, decyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group; methoxy group, ethoxy group, propoxy group , A butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a decyloxy group, etc., an alkoxy group having 1 to 10 carbon atoms; a hydroxyl group; or a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, etc. Is mentioned.

R ₂₁ and R ₂₂ , R ₂₃ and R ₂₄ , R ₂₅ and R ₂₆ , R ₂₇ and R ₂₈ are connected to each other, and — (CH ₂ ) ₃ —, — (CH ₂ ) ₄ —, — (CH _{2) 5} -, etc. may form an aliphatic carbocyclic ring.

In the general formula (II), as R _{21 to} R ₂₈ , (1) a linear or branched alkyl group optionally having an alkoxy group or a halogen atom as a substituent, (2) a cycloalkyl group which may have a linear or branched alkyl group as a substituent, (3) an aryl group which may have an alkyl group, an alkoxy group or a halogen atom as a substituent , (4) a halogen atom, or (5) each of which is linked to form an aliphatic carbocycle, preferably a linear or branched alkyl group having 1 to 8 carbon atoms or-( It is more preferable that CH ₂ ) ₃ — or — (CH ₂ ) ₄ — is formed, and at least four groups of R _{21 to} R ₂₈ are alkyl groups and the rest are hydrogen atoms, or R ₂₁ And R ₂₂ , R ₂₃ and R ₂₄ , R ₂₅ and It is particularly preferred that R ₂₆ , R ₂₇ and R ₂₈ are linked to form an aliphatic carbocycle such as — (CH ₂ ) ₃ —, — (CH ₂ ) ₄ —, — (CH ₂ ) ₅ — and the like. .

In the general formula (II), M ₂ is 2 hydrogen atoms; or 2 groups, 3 groups, 4 groups, 8 groups, 9 groups, 10 groups of the periodic table based on the rules of inorganic chemical nomenclature 1990 A divalent metal atom, a trivalent monosubstituted metal atom, a tetravalent disubstituted metal atom or an oxymetal atom selected from elements belonging to Group 11, Group 12, Group 13, Group 14 or Group 15, Specific examples of the divalent metal atom include Cu, Zn, Fe, Co, Ni, Ru, Rd, Pd, Mn, Sn, Mg, and Ti, and the trivalent monosubstituted metal atom includes Al. -Cl, Ga-Cl, In-Cl, Fe-Cl, Ru-Cl, and the like include metal atoms monosubstituted by halogen atoms, hydroxyl groups or alkoxy groups. Examples of tetravalent disubstituted metals include SiCl ₂ , GeCl ₂ , TiCl ₂ , SnCl ₂ , Si (OH) ₂ , Ge (OH) ₂ , Mn (OH) ₂ , Sn (OH) _{2, and the} like, and metal atoms that are disubstituted by a hydroxyl group or an alkoxy group are exemplified. Examples of the oxymetal include VO, MnO, and TiO. Can be mentioned. Of these, VO, Cu, Ni, and Co are preferable, and VO and Cu are more preferable.

  Below, the preferable specific example of the tetraaza porphyrin-type compound represented by general formula (II) is shown.

[In the formula (III), each R ₃₁ independently represents an alkyl group which may have a substituent, an alkoxy group which may have a substituent, or an cycloalkyl which may have a substituent. group, an optionally substituted aryl group, an optionally substituted aryl group, or a halogen atom, W ₃ -X ₃ W ₃ in the -R ₃₂ are each independently , An imino group, an alkylimino group, or an oxygen atom, each of X ₃ independently represents a carbonyl group or a sulfonyl group, each of R ₃₂ independently represents a monovalent group or a hydrogen atom, ₃ and l ₃ ′ are each independently an integer of 0 to 5, m ₃ and m ₃ ′ are each independently an integer of 0 to 5, n and n ₃ ′ are n ₃ + n ₃ ′ ≧ 0 An integer of ₃ , l ₃ + m ₃ + n ₃ ≦ 5, and l ₃ ′ + m ₃ ′ + n ₃ ′ ≦ 5, and R ₃₁ and W on the benzene ring When there are a plurality of _3- X ₃ -R _{32 s} , R ₃₁ and W ₃ -X ₃ -R ₃₂ are different from each other in one benzene ring and the other benzene ring. May be. ]

Examples of the alkyl group represented by R ₃₁ in the general formula (III) include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a decyl group, an undecyl group, a dodecyl group, and a tridecyl group. A linear or branched group having 1 to 20 carbon atoms, such as a group or a pentadecyl group, and examples of the alkoxy group for R ₃₁ include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentyloxy group. Linear or branched chain having 1 to 20 carbon atoms such as hexyloxy group, heptyloxy group, octyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, tridecyloxy group, pentadecyloxy group, etc. things, also as the cycloalkyl group for R _31, a, for example, cyclopropyl group, cyclobutyl group, cyclopentyl group Cyclohexyl group, those having 3 to 20 carbon atoms such as cycloheptyl group, The aryl group for R _31, for example, a phenyl group, a naphthyl group and the like, also, as the aryloxy group for R ₃₁ is, for example, Examples thereof include a phenoxy group, a naphthyloxy group, and the like, and examples of the halogen atom for R ₃₁ include a fluorine atom, a chlorine atom, and a bromine atom.

  Examples of the substituent for the alkyl group, alkoxy group, cycloalkyl group, aryl group, and aryloxy group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. Group, linear or branched alkyl group having 1 to 10 carbon atoms such as decyl group, methoxy group, ethoxy group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group C1-C10 alkoxy group such as decyloxy group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, etc., C3-C10 cycloalkyl group, hydroxyl group, fluorine atom, chlorine A halogen atom such as an atom or a bromine atom is exemplified.

In the general formula (III), as R ₃₁ , (1) an alkoxy group, a hydroxyl group, or a linear or branched alkyl group optionally having a halogen atom as a substituent, 2) A linear or branched alkoxy group optionally having an alkoxy group as a substituent, (3) an alkyl group, an alkoxy group, or an aryl group optionally having a halogen atom as a substituent; 4) an alkyl group, an alkoxy group, or an aryloxy group optionally having a halogen atom as a substituent, or (5) a halogen atom, preferably a linear or branched alkyl group having 1 to 8 carbon atoms Or a linear or branched alkoxy group having 1 to 8 carbon atoms is particularly preferred.

The alkyl group in the alkylimino group of W ₃ in W ₃ -X ₃ -R ₃₂ in the formula (III), is preferably a straight-chain or branched-chain having 1 to 8 carbon atoms, W _{As 3} , an imino group or an alkylimino group is preferable, and an imino group is particularly preferable. When X ₃ is a sulfonyl group, R ₃₂ is not a hydrogen atom.

Further, W ₃ as a monovalent group of R ₃₂ in -X ₃ -R _32, for example, the same alkyl groups as exemplified as the alkyl group for R _31, the same alkoxy groups as mentioned as the alkoxy group in the R ₃₁ the same cycloalkyl groups as mentioned as the cycloalkyl group of R _31, the same aryl groups as exemplified as the aryl group in R _31, the same aryloxy groups and mentioned as the aryl group in said R _31, and amino And heterocyclic groups such as 3-pyridyl group, 2-furyl group, 2-tetrahydrofuryl group, 2-thienyl group, etc., and these alkyl groups, alkoxy groups, cycloalkyl groups, aryl groups, aryl oxy group, an amino group, and heterocyclic group include an alkyl group in the R _31, alkoxy groups, cycloalkyl groups The same alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a halogen atom, or an aryl group, which is the same as the substituent for the aryl group and aryloxy group. You may have a group etc. as a substituent.

Of the R ₃₂ , the same alkyl group as the preferred group of R _31, a phenyl group optionally substituted with an alkyl group having 1 to 8 carbon atoms, or an alkyl group having 1 to 8 carbon atoms A good phenyl group may be a 2-furyl group which may be substituted with an alkyl group having 1 to 8 carbon atoms, a 2-tetrahydrofuryl group which may be substituted with an alkyl group having 1 to 8 carbon atoms, or carbon. A cyclohexyl group which may be substituted with an alkyl group of 1 to 8 is particularly preferable.

In the above general formula, l ₃ and l ₃ ′ are each independently an integer of 0 to 5, m ₃ and m ₃ ′ are each independently an integer of 0 to 5, n ₃ and n ₃ ′ are n ₃ 'in ≧ 1 and is an integer of 0 to _{3, l 3 + m 3 + n} 3 ≦ 5, and l _3' + n ₃ in + m ₃ '+ n _3' is a ≦ 5, l ₃ and l ₃ 'is 1 or more, It is preferable that l ₃ + m ₃ + n ₃ ≦ 3 and l ₃ ′ + m ₃ ′ + n ₃ ′ ≦ 3, and more preferably m ₃ and m ₃ ′ are zero. Further, when R ₃₁ and W ₃ -X ₃ -R ₃₂ are a plurality each present on the benzene ring, each of R ₃₁ and W ₃ -X ₃ -R _32, in one benzene ring, and the other The benzene rings may be different from each other. Also, adjacent R ₃₁ on one benzene ring may be linked to each other to form an alkanediyl group, an alkylenedioxy group, or the like to form a cyclic structure.

  Preferable examples of the squarylium compound of the general formula (III) having an absorption maximum at 570 to 605 nm include the compounds exemplified in Japanese Patent Application No. 2001-265276. Among them, specific preferred examples are shown below.

[(In the formula (IV), -T ₄ - are each independently an oxygen atom, a sulfur atom, or, -CR ₄₁ R ₄₂ - independently of the group (R ₄₁ and R ₄₂ represented by the number of carbon atoms represents 1-4 alkyl group, R ₄₁ and R ₄₂ are oxygen connected, sulfur, nitrogen atom may also form a good 3-6 membered ring include.), and, Y ₄ are each independently X ₄ represents each independently a hydrogen atom, a halogen atom, an alkyl group, or an aryl group, and R ₄₀ each independently represents a halogen atom, a nitro group, an alkoxy group, or an aryl group. ^{Represents a} group, k ₄ represents 1 or 2, An ₄ ^m4- represents an m ₄ valent anion, m ₄ represents an integer of 1 or 2, and p ₄ represents a coefficient for keeping the charge neutral. .]

In the general formula (IV), examples of the alkyl group having 1 to 4 carbon atoms represented by R ₄₁ and R ₄₂ include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, and sec-butyl. , Isobutyl and the like. In addition, the 3- to 6-membered ring formed by connecting R ₄₁ and R ₄₂ may contain oxygen, sulfur, and nitrogen atoms, and cyclopropane-1,1-diyl, cyclobutane-1,1-diyl, 2, 4-dimethylcyclobutane-1,1-diyl, 3-dimethylcyclobutane-1,1-diyl, cyclopentane-1,1-diyl, cyclohexane-1,1-diyl, tetrahydropyran-4,4-diyl, thian- 4,4-diyl, piperidine-4,4-diyl, N-substituted piperidine-4,4-diyl, morpholine-2,2-diyl, morpholine-3,3-diyl, N-substituted morpholine-2,2- Examples include diyl and N-substituted morpholine-3,3-diyl, which may have a substituent.

The organic group represented by Y ₄ is not particularly limited, and examples thereof include methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, hexyl, cyclohexyl, Cyclohexylmethyl, 2-cyclohexylethyl, heptyl, isoheptyl, tertiary heptyl, n-octyl, isooctyl, tertiary octyl, 2-ethylhexyl, nonyl, isononyl, decyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, peptadecyl, octadecyl, etc. A linear, branched or cyclic alkyl group having 1 to 8 carbon atoms; vinyl, 1-methylethenyl, 2-methylethenyl, propenyl, butenyl, isobutenyl, pentenyl, hexenyl, heptenyl, octenyl, decenyl Alkenyl groups such as pentadecenyl and 1-phenylpropen-3-yl; phenyl, naphthyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-vinylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 4-butylphenyl, 4-isobutylphenyl, 4-tert-butylphenyl, 4-hexylphenyl, 4-cyclohexylphenyl, 4-octylphenyl, 4- (2-ethylhexyl) phenyl, 4-stearylphenyl, 2,3- Dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4-ditert-butylphenyl, cyclohexylphenyl Alkylaryl groups such as benzyl and phenethyl Aryl, 2-phenylpropan-2-yl, diphenylmethyl, triphenylmethyl, styryl, cinnamyl and the like; 2-methoxyethyl, 3-methoxypropyl, 4-methoxybutyl, 2-butoxyethyl, methoxyethoxyethyl , Methoxyethoxyethoxyethyl, 3-methoxybutyl, 2-phenoxyethyl, 2-methylthioethyl, 2-phenylthioethyl, etc., alkyl groups, alkenyl groups, alkylaryl groups or arylalkyl groups are interrupted by ether bonds or thioether bonds. And the like. Further, these groups may be substituted with an alkoxy group, an alkenyl group, a nitro group, a cyano group, a halogen atom or the like.

Examples of the halogen atom represented by X ₄ include fluorine, chlorine, bromine and iodine atoms, and examples of the alkyl group and aryl group include the same groups as those exemplified in the description of Y _4. .

Examples of the halogen atom represented by R ₄₀ include fluorine, chlorine, bromine, and iodine atoms. Examples of the alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an iso-butyloxy group, Examples thereof include linear, branched or cyclic alkoxy groups having 1 to 8 carbon atoms such as n-hexyloxy group, cyclohexyloxy group and n-octyloxy group, and the aryl group is exemplified in the section of Y ₄ . The thing similar to a thing is mentioned.

^Examples of the anion represented by An ₄ ^m4- include monovalent monovalent halogen anions such as chlorine anion, bromine anion, iodine anion and fluorine anion; perchlorate anion, chlorate anion, thiocyanate anion, six Inorganic anions such as phosphorus fluoride anion, antimony hexafluoride anion, boron tetrafluoride anion, organic sulfonate anions such as benzenesulfonate anion, toluenesulfonate anion, trifluoromethanesulfonate anion; octyl phosphate anion, dodecyl phosphorus Organic phosphate anions such as acid anion, octadecyl phosphate anion, phenyl phosphate anion, nonylphenyl phosphate anion, 2,2′-methylenebis (4,6-ditert-butylphenyl) phosphonate anion, bis (tri Fluoromethylsulfo Sulfonylimide anions such as (nyl) imide anion, and the like. Examples of divalent ones include benzene disulfonate anion and naphthalenedisulfonate anion. Further, a quencher anion which is a metal complex compound can be used as necessary.

  Examples of the quencher anion include anions described in JP-A-60-234892 and JP-A-2002-350632. For example, the anion represented by the following general formula (A) and (B) is mentioned.

(Wherein R ₄₃ and R ₄₄ are each independently a hydrogen atom, a halogen atom, an alkyl group, an aryl group, —SO ₂ —Z ₄ group (Z ₄ is a dialkylamino group, a diarylamino group, a piperidino group, a morpholino group) And a ₄ and b ₄ each independently represents an integer of 0 to 3. R ₄₅ , R ₄₆ , R ₄₇ and R ₄₈ each independently represent an alkyl group, an alkylphenyl group, or an alkoxyphenyl group. Represents a group or a halogenated phenyl group, and M ₄ represents a nickel or copper atom.)

In the general formula (A), examples of the halogen atom for the substituents R ₄₃ and R ₄₄ include fluorine, chlorine, bromine, and iodine atoms, and examples of the alkyl group and aryl group include the general formula (IV). of include those similar to those exemplified in the section of a substituent Y _4.
Examples of the alkyl group of the dialkylamino group of Z ₄ include a linear or branched alkyl group having 1 to 8 carbon atoms. Examples of the aryl group of the diarylamino group of Z ₄ include a fluorine atom, a chlorine atom, bromine Examples thereof include a phenyl group which may be substituted with an atom.

As the substituents R ₄₃ and R ₄₄ , electron withdrawing groups are preferable, and in particular, 2,3,5-trichloro group, 2,3-dichloro group, 2,4-dichloro group, 2,5-dichloro group, — SO ₂ Z ₄ is preferred. Z ₄ is preferably a dimethylamino group, a diethylamino group, a di-n-propylamino group, a di-n-butylamino group, a piperidino group or a morpholino group, and particularly preferably a morpholino group.

In the general formula (B), examples of the alkyl group of R ₄₅ , R ₄₆ , R ₄₇ and R _{48 and} the alkyl group of the alkylphenyl group include those exemplified in the section of the substituent Y _{4 in} the general formula (IV). The same thing is mentioned. Examples of the alkoxy group of the alkoxyphenyl group include the same groups as those exemplified in the section of the substituent R _{40 in} the general formula (IV). Examples of the halogen of the halogenated phenyl group include a fluorine atom, a chlorine atom, and bromine. An atom and an iodine atom are mentioned.

 Specific examples of suitable cyanine dyes of the general formula (IV) having an absorption maximum at 570 to 605 nm are listed in Table 1 below.

  Among the compounds listed above, more preferred compounds having an absorption maximum at 570 to 605 nm are tetraazaporphyrin compounds represented by general formula (II) and squarylium compounds represented by general formula (III). It is.

  The electronic display filter of the present invention can contain a compound having an absorption maximum at 380 to 420 nm in order to further improve color purity and contrast. Examples of the compound having an absorption maximum at 380 to 420 nm include compounds of the following general formula (V).

[In Formula (V), R ₅₃ represents an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an aryl group which may have a substituent, or hydrogen. R ₅₁ represents each independently an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an alkoxycarbonyl group which may have a substituent, a substituent A cycloalkyl group which may have a group, an aryl group which may have a substituent, an aryloxy group which may have a substituent, an aryloxycarbonyl group which may have a substituent Represents an optionally substituted amino group or a hydrogen atom, and each R ₅₂ independently represents an optionally substituted alkyl group or an optionally substituted cycloalkyl. Group, aryl group optionally having substituent (s), or hydrogen Shows the child, Y ₅ each independently represents an oxygen atom, or an imino group, these R _51, R _52, and Y ₅ may be different from each other between both of the pyrazole ring. ]

Examples of the alkyl group of the substituents R ₅₃ and R ₅₂ in the general formula (V) include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a decyl group, and an undecyl group. Straight chain or branched chain groups having 1 to 20 carbon atoms such as a group, dodecyl group, tridecyl group, pentadecyl group, etc., and examples of the cycloalkyl group of R ₅₃ and R ₅₂ include, for example, cyclopropyl group, cyclobutyl Group, cyclopentyl group, cyclohexyl group, cycloheptyl group and the like having 31 to 20 carbon atoms, and examples of R ₅₃ and R ₅₂ aryl groups include phenyl group and naphthyl group, respectively.

Examples of the substituent for the alkyl group, cycloalkyl group, and aryl group of R ₅₃ and R ₅₂ include, for example, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, C1-C10 alkyl groups, such as a decyl group, such as C1-C10 alkyl groups, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a decyloxy group Aryl groups such as alkoxy groups, phenyl groups, naphthyl groups, aryloxy groups such as phenoxy groups, naphthyloxy groups, sulfonamido groups, alkylsulfonamido groups, dialkylsulfonamido groups, nitro groups, hydroxy groups, and fluorine atoms, Halogen atoms such as a chlorine atom and a bromine atom are exemplified.

In the general formula (V), as R ₅₃ and R ₅₂ , (1) an alkoxy group, an aryl group, an aryloxy group, a hydroxyl group, or a halogen atom may be used as a substituent. It may have a chain or branched alkyl group, (2) an alkyl group, an alkoxy group, a sulfonamide group, an alkylsulfonamide group, a dialkylsulfonamide group, a nitro group, a hydroxyl group, or a halogen atom as a substituent. An aryl group or (3) a hydrogen atom is preferable. Particularly, R ₅₃ is preferably a hydrogen atom, a linear or branched alkyl group having 1 to 8 carbon atoms, or a phenyl group, and R ₅₂ is A linear or branched alkyl group having 1 to 8 carbon atoms or a phenyl group optionally having an alkyl group or a halogen atom as a substituent is preferred.

In addition, the alkyl group of R ₅₁ in the general formula (V) is the same as the alkyl group in R ₅₃ and R ₅₂ , and the alkoxy group of R ₅₁ is, for example, a methoxy group or ethoxy group Group, propoxy group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, tridecyloxy group, pentadecyloxy group, etc. A linear or branched group of ˜20, an alkoxycarbonyl group of R ₅₁ is a carbonyl group having the alkoxy group, and a cycloalkyl group of R ₅₁ is the R ₅₃ and R the same as mentioned as the cycloalkyl group in _52, the aryl group, the aryl in the R ₅₃ and R ₅₂ The same as mentioned as are also Examples of the aryloxy group R _51, phenoxy group, naphthyloxy group and the like, As the aryloxycarbonyl group R _51, the carbonyl group having an aryloxy group, Each is listed.

Examples of the substituent of the alkyl group, alkoxy group, alkoxycarbonyl group, cycloalkyl group, aryl group, aryloxy group, aryloxycarbonyl group, and amino group of R ₅₁ include, for example, the alkyl in R ₅₃ and R ₅₂ described above. Group, cycloalkyl group, and the same alkyl group as the substituent of the aryl group, the same alkoxy group, the same aryl group, the same aryloxy group, the same sulfonamide group, the same alkylsulfonamide group, the same dialkylsulfonamide group, Similarly, a nitro group, a halogen atom, an acyl group such as a propionyl group, a butyryl group, and a benzoyl group, a sulfonyl group such as a methanesulfonyl group and a benzenesulfonyl group, a hydroxyl group, a halogen atom, and the like.

In the general formula (V), as R ₅₁ , in the above, (1) a linear or optionally substituted alkoxy group, aryl group, aryloxy group, hydroxyl group, or halogen atom may be used. A branched alkyl group, (2) a linear or branched alkoxy group optionally having an alkoxy group as a substituent, and (3) an alkoxy group optionally having an alkoxy group as a substituent A carbonyl group, (4) an alkyl group, an alkoxy group, a sulfonamide group, an alkylsulfonamide group, a dialkylsulfonamide group, a nitro group, a hydroxyl group, or an aryl group optionally having a halogen atom as a substituent, (5) A carbonyl group having an aryl group optionally having an alkyl group or an alkoxy group as a substituent, or (6) an alkyl group or an acyl group , Or a sulfonyl group to an amino group which may have a substituent, are preferable, particularly preferably a linear or branched alkyl group having 1 to 8 carbon atoms.

In the general formula (V), Y ₅ represents an oxygen atom or an imino group, and an oxygen atom is preferable. Furthermore, in the present invention, as the dipyrazolylmethine compound represented by the general formula (V), R ₅₁ , R ₅₂ , and Y ₅ may be different from each other between both pyrazole rings. In addition, those which are left and right objects with a methine group in between are preferable.

As a compound having an absorption maximum at 380 to 420 nm, among compounds of general formula (V), Y ₅ is an oxygen atom, R ₅₃ is a hydrogen atom, and R ₅₁ and R ₅₂ have a substituent. The case of a good alkyl group or an aryl group which may have a substituent is particularly preferred.
The preferable specific example is shown below.

  The electronic display filter of the present invention can contain a compound having an absorption maximum at 480 to 520 nm in order to further improve color purity and contrast. Examples of the compound having an absorption maximum at 480 to 520 nm include a squarylium compound represented by the general formula (VI) and a dipyrromethene compound represented by the general formula (VII).

[In formula (VI), each R ₆₁ independently represents an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, or an aryl which may have a substituent. R ₆₂ represents a group or a hydrogen atom, and each R ₆₂ independently represents an alkyl group which may have a substituent, an alkoxy group which may have a substituent, or an alkoxy which may have a substituent. Carbonyl group, optionally substituted cycloalkyl group, optionally substituted aryl group, optionally substituted aryloxy group, optionally substituted An aryloxycarbonyl group, an amino group optionally having a substituent, a hydroxyl group, or a hydrogen atom is shown, and these R ₆₁ and R ₆₂ may be different from each other between both pyrazole rings. ]

Examples of the alkyl group of the substituent R ₆₁ in the general formula (VI) include, for example, methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, undecyl group, dodecyl group. A straight chain or branched chain group having 1 to 20 carbon atoms such as a group, a tridecyl group, or a pentadecyl group, and examples of the cycloalkyl group represented by R ₆₁ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. Groups having 3 to 20 carbon atoms such as a cycloheptyl group, and examples of the aryl group for R ₆₁ include a phenyl group and a naphthyl group.

  Examples of the substituent for the alkyl group, the cycloalkyl group, and the aryl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a decyl group. An alkoxy group having 1 to 10 carbon atoms such as an alkyl group having 1 to 10 carbon atoms, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, and a decyloxy group; Aryl group such as phenyl group, naphthyl group, aryloxy group such as phenoxy group, naphthyloxy group, formamino group, alkylcarbonylamino group, alkylsulfonylamino group, aminocarbonyl group, alkylaminocarbonyl group, dialkylaminocarbonyl group, Aminosulfonyl group, alkylaminosulfur Group, a dialkylamino sulfonyl group, an amino group, a nitro group, a hydroxyl group, and a fluorine atom, a chlorine atom and a halogen atom such as a bromine atom.

In the general formula (VI), as R ₆₁ , in the above, (1) a linear or optionally substituted alkoxy group, aryl group, aryloxy group, hydroxyl group, or halogen atom may be used. A branched alkyl group, or (2) an aryl group optionally having an alkyl group, an alkoxy group, an amino group, an alkylcarbonylamino group, an alkylsulfonylamino group, a nitro group, a hydroxyl group, or a halogen atom as a substituent, In particular, a linear or branched alkyl group having 1 to 8 carbon atoms which may have an alkoxy group as a substituent is preferable.

In addition, the alkyl group of R ₆₂ in the general formula (VI) is the same as the alkyl group in R ₆₁ , and the alkoxy group of R ₆₂ is, for example, a methoxy group, an ethoxy group, or a propoxy group. Group, butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, decyloxy group, undecyloxy group, dodecyloxy group, tridecyloxy group, pentadecyloxy group, etc. a straight chain or branched chain shape, as the alkoxycarbonyl group R _62, the carbonyl group having an alkoxy group, and the cycloalkyl group R _62, cycloalkyl group for R ₆₁ those similar to the exemplified, as the aryl group, the same as mentioned as the aryl group for R ₆₁ The is also aryloxy groups R _62, phenoxy group, naphthyloxy group and the like, As the aryloxycarbonyl group R _62, the carbonyl group having an aryloxy group, and the like, respectively.

Examples of the substituent of the alkyl group, alkoxy group, alkoxycarbonyl group, cycloalkyl group, aryl group, aryloxy group, aryloxycarbonyl group, and amino group include, for example, the alkyl group and cycloalkyl group in R ₆₁ . And the same alkyl group as mentioned as the substituent of the aryl group, the same alkoxy group, the same aryl group, the same aryloxy group, the same sulfonamide group, the same alkylsulfonamide group, the same dialkylsulfonamide group, the same nitro group, the same Examples include halogen atoms, acyl groups such as propionyl group, butyryl group, and benzoyl group, sulfonyl groups such as methanesulfonyl group and benzenesulfonyl group, hydroxyl groups, and halogen atoms.

In the general formula (VI), as R ₆₂ , in the above, (1) a linear or optionally substituted alkoxy group, aryl group, aryloxy group, hydroxyl group, or halogen atom may be used. A branched alkyl group, (2) an alkoxy group, an aryl group, an aryloxy group, a hydroxyl group, or a linear or branched alkoxy group optionally having a halogen atom as a substituent, and (3) an alkoxy group A carbonyl group having an alkoxy group which may have as a substituent, (4) an alkyl group, an alkoxy group, a sulfonamide group, an alkylsulfonamide group, a dialkylsulfonamide group, a nitro group, a hydroxyl group, or a halogen atom as a substituent May have an aryl group, (5) an alkyl group, or an alkoxy group as a substituent. A carbonyl group having a reel group, or (6) an amino group optionally having an alkyl group, an acyl group, or a sulfonyl group as a substituent is preferable, and an alkoxy group may be particularly preferable as a substituent. The linear or branched alkoxy group which may have a C1-C8 linear or branched alkyl group and alkoxy group as a substituent is preferable.
Specific examples are shown below.

Wherein (VII), each independently R ₇₁ to R _77, a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an optionally substituted amino group, it may be esterified Carboxyl group, sulfonic acid group, acyl group, acyloxy group, alkyl group optionally having substituent, alkoxy group optionally having substituent, alkylthio group optionally having substituent, substituted An alkenyl group which may have a group, an aryl group which may have a substituent, an aryloxy group which may have a substituent, an arylthio group which may have a substituent, a substituent Represents a heterocyclic group optionally having a substituent, a heterocyclic oxy group optionally having a substituent, and a carbamoyl group optionally having a substituent, and R ₇₁ and R ₇₂ or R ₇₆ and R _77. Each may be linked and have a substituent. An aromatic ring may be formed. M ₇ represents a metal atom. ]

Examples of the halogen atom represented by R _{71 to} R ₇₇ in the general formula (VII) include a fluorine atom, a chlorine atom, and a bromine atom.
Examples of the amino group optionally having a substituent represented by R _{71 to} R ₇₇ include an amino group, an acylamino group optionally having a substituent, and an alkylamino group optionally having a substituent. And optionally substituted dialkylamino group, arylamino group, diarylamino group, alkylarylamino group and the like. Examples of the acylamino group which may have a substituent include an alkylcarbonylamino group which may have a substituent and an arylcarbonylamino group which may have a substituent.

Examples of the alkylamino group or dialkylamino group include methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, undecyl group, dodecyl group, pentadecyl group and the like. Examples thereof include amino groups that are mono- or di-substituted with ˜20 alkyl groups.
Examples of the arylamino group or diarylamino group include an amino group that is mono- or di-substituted with an aryl group having 6 to 12 carbon atoms such as a phenyl group or a naphthyl group.
The alkylarylamino group has 1 to 20 carbon atoms such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, undecyl group, dodecyl group, pentadecyl group, etc. Examples thereof include an amino group substituted with an alkyl group and an aryl group having 6 to 12 carbon atoms such as a phenyl group and a naphthyl group.

Examples of the alkylcarbonylamino group include those having 2 to 20 carbon atoms such as an acetylamino group, an ethylcarbonylamino group, and a butylcarbonylamino group.
Examples of the arylcarbonylamino group include those having 7 to 20 carbon atoms such as a phenylcarbonylamino group, a 4-ethylphenylcarbonylamino group, and a 3-butylphenylcarbonylamino group.
As the substituent bonded to the acyl group, alkyl group and aryl group of these acylamino groups, alkylamino groups, dialkylamino groups, arylamino groups, diarylamino groups or alkylarylamino groups, an alkyl group having 1 to 10 carbon atoms , A C1-C10 alkoxy group, a hydroxyl group, a halogen atom, etc. are mentioned.

Examples of the optionally esterified carboxyl group represented by R _{71 to} R ₇₇ include a carboxyl group, an optionally substituted alkoxycarbonyl group, and an optionally substituted aryloxycarbonyl group. And an alkenyloxycarbonyl group which may have a substituent.

  Examples of the alkoxycarbonyl group include C2-C20 alkoxycarbonyl groups such as a methoxycarbonyl group, an ethoxycarbonyl group, an isopropyloxycarbonyl group, and a 2,4-dimethylbutyloxycarbonyl group. Further, an aryl group having 6 to 12 carbon atoms, an alkoxycarbonyl group having 2 to 10 carbon atoms, an alkylcarbonyl group having 2 to 10 carbon atoms, and the like may be bonded to the alkoxycarbonyl group as a substituent. Examples of those having such a substitution machine include aralkyloxycarbonyl groups having 8 to 20 carbon atoms such as benzyloxycarbonyl group and phenethyloxycarbonyl group, methoxycarbonylmethoxycarbonyl group, ethoxycarbonylmethoxycarbonyl group, n-propoxycarbonyl group. C4-C20 alkoxycarbonylalkoxycarbonyl groups such as methoxycarbonyl group and isopropoxycarbonylmethoxycarbonyl group, C4-C20 alkylcarbonylalkoxycarbonyl groups such as methylcarbonylmethoxycarbonyl group and ethylcarbonylmethoxycarbonyl group. It is done. These aralkyloxycarbonyl group, alkoxycarbonylalkoxycarbonyl group, and alkylcarbonylalkoxycarbonyl group may further have the above-described substituent.

Examples of the aryloxycarbonyl group include a phenoxycarbonyl group or a naphthyloxycarbonyl group which may be substituted with an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a hydroxyl group, a halogen atom, or the like. Examples of the alkylphenoxycarbonyl group include those having 7 to 20 carbon atoms such as 2-methylphenoxycarbonyl group and 4-t-butylphenoxycarbonyl group. Examples of the alkoxyphenoxycarbonyl group include 4-methoxyphenoxycarbonyl group. The thing of C7-20 is mentioned. These alkylphenoxycarbonyl groups and alkoxyphenoxycarbonyl groups may further have the above-described substituents.
Examples of the alkenyloxycarbonyl group include those having 3 to 20 carbon atoms such as an allyloxycarbonyl group and a 2-butenoxycarbonyl group. Examples of the substituent for the alkenyloxycarbonyl group include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a hydroxyl group, and a halogen atom.

Examples of the acyl group represented by R _{71 to} R ₇₇ include formyl group, acetyl group, ethylcarbonyl group, n-propylcarbonyl group, iso-propylcarbonyl group, n-butylcarbonyl group, iso-butylcarbonyl group, sec- One having 1 to 20 carbon atoms such as butylcarbonyl group, t-butylcarbonyl group, n-pentylcarbonyl group, iso-pentylcarbonyl group, neo-pentylcarbonyl group, 2-methylbutylcarbonyl group, benzylcarbonyl group, benzoyl group Is mentioned. Examples of the substituent for the acyl group include a halogen atom, a nitro group, a hydroxyl group, a cyano group, an alkoxy group, and an aryloxy group. Examples of the acyl group substituted with a halogen atom include a chlorobenzylcarbonyl group. Examples of the acyl group substituted with a nitro group include a nitrobenzylcarbonyl group. Examples of the acyl group substituted with a hydroxyl group include a hydroxybenzylcarbonyl group and a hydroxy group. Examples of the acyl group substituted with a cyano group include a cyanobenzylcarbonyl group and a cyanopentylcarbonyl group. Examples of the acyl group substituted with an alkoxy group include a methoxybenzylcarbonyl group and the like. Examples of the acyl group substituted with an oxy group include a phenoxybenzylcarbonyl group.
Examples of the acyl group of the acyloxy group represented by R _{71 to} R ₇₇ include the same as those described above.

The alkyl groups represented by R ₇₁ to R _77, a methyl group, an ethyl group, n- propyl group, iso- propyl, n- butyl, iso- butyl group, sec- butyl group, t- butyl group, n-pentyl group, iso-pentyl group, 2-methylbutyl group, 1-methylbutyl group, neo-pentyl group, 1,2-dimethylpropyl group, 1,1-dimethylpropyl group, cyclo-pentyl group, n-hexyl group 4-methylpentyl group, 3-methylpentyl group, 2-methylpentyl group, 1-methylpentyl group, 3,3-dimethylbutyl group, 2,3-dimethylbutyl group, 1,3-dimethylbutyl group, 2 , 2-dimethylbutyl group, 1,2-dimethylbutyl group, 1,1-dimethylbutyl group, 3-ethylbutyl group, 2-ethylbutyl group, 1-ethylbutyl group, 1,2,2-trimethylbutyl group, 1, 1,2-trimethylbutyl group, 1-ethyl-2-methylpropyl group, cyclo-hexyl group, n-heptyl group, 2-methylhexyl group, 3 -Methylhexyl group, 4-methylhexyl group, 5-methylhexyl group, 2,4-dimethylpentyl group, n-octyl group, 2-ethylhexyl group, 2,5-dimethylhexyl group, 2,5,5-trimethyl Pentyl group, 2,4-dimethylhexyl group, 2,2,4-trimethylpentyl group, n-octyl group, 3,5,5-trimethylhexyl group, n-nonyl group, n-decyl group, 4-ethyloctyl Group, 4-ethyl-4,5-methylhexyl group, n-undecyl group, n-dodecyl group, 1,3,5,7-tetraethyloctyl group, 4-butyloctyl group, 6,6-diethyloctyl group, n-tridecyl group, 6-methyl-4-butyloctyl group, n-tetradecyl group, n-pentadecyl group, 3,5-dimethylheptyl group, 2,6-dimethylheptyl group, 2,4-dimethylheptyl group, 2 , 2,5,5-Tetramethylhexyl group, 1-cyclo-pentyl-2,2-dimethylpropyl group, 1-cyclo-hexyl-2,2-dimethylpropyl group Examples thereof include straight-chain, branched-chain or cyclic ones having 1 to 20 carbon atoms.

Examples of the substituent for the alkyl group include a halogen atom, an alkoxy group having 1 to 10 carbon atoms, an aryl group, a hydroxyl group, and a cyano group.
As a haloalkyl group, C1-C20 haloalkyl groups, such as a chloromethyl group, a dichloromethyl group, a fluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, a nonafluorobutyl group, are mentioned.
Examples of the alkoxyalkyl group include C2-C20 alkoxyalkyl groups such as a methoxyethyl group, an ethoxyethyl group, an iso-propyloxyethyl group, a 3-methoxypropyl group, and a 2-methoxybutyl group.

  Examples of the aralkyl group include a benzyl group and a naphthylmethyl group. Examples of the substituent for the aralkyl group include a nitro group, a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a halogen atom, and the like. Examples of the aralkyl group having a substituent include nitrobenzyl group, cyanobenzyl group, hydroxybenzyl group, methylbenzyl group, dimethylbenzyl group, trimethylbenzyl group, dichlorobenzyl group, methoxybenzyl group, ethoxybenzyl group, and trifluoromethyl. Examples thereof include those having 7 to 20 carbon atoms such as benzyl group, naphthylmethyl group, nitronaphthylmethyl group, cyanonaphthylmethyl group, hydroxynaphthylmethyl group, methylnaphthylmethyl group, trifluoromethylnaphthylmethyl group and the like.

Examples of the hydroxyalkyl group include those having 1 to 20 carbon atoms such as a hydroxymethyl group, a hydroxyethyl group, a hydroxypropyl group, and a hydroxybutyl group.
Examples of the cyanoalkyl group include those having 2 to 20 carbon atoms such as a cyanomethyl group, a cyanoethyl group, a cyanopropyl group, and a cyanobutyl group.

The alkoxy group represented by R ₇₁ to R _77, a methoxy group, an ethoxy group, n- propoxy group, iso- propoxy group, n- butoxy group, iso- butoxy group, sec- butoxy group, t-butoxy group, Examples thereof include linear or branched alkoxy groups having 1 to 20 carbon atoms such as n-pentoxy group, iso-pentoxy group, neo-pentoxy group, n-hexyloxy group, and n-dodecyloxy group. Examples of the substituent include an alkoxy group having 1 to 10 carbon atoms, a halogen atom, and an aryl group. Examples of the alkoxyalkoxy group include those having 2 to 20 carbon atoms such as a methoxyethoxy group, an ethoxyethoxy group, a 3-methoxypropyloxy group, and a 3- (iso-propyloxy) propyloxy group. Examples of the haloalkoxy group include those having 1 to 20 carbon atoms such as a trifluoromethoxy group. Examples of the aralkyloxy group include those having 7 to 20 carbon atoms such as a benzyloxy group.

The alkylthio group represented by R ₇₁ to R _77, methylthio group, ethylthio group, n- propylthio group, iso- propylthio group, n- butylthio group, iso- butylthio, sec- butylthio, t-butylthio group, n-pentylthio, iso-pentylthio, 2-methylbutylthio, 1-methylbutylthio, neo-pentylthio, 1,2-dimethylpropylthio, 1,1-dimethylpropylthio, etc. The alkylthio group of 1-20 is mentioned, A halogen atom, an aryl group, etc. are mentioned as a substituent of an alkylthio group. Examples of the haloalkylthio group include a trifluoromethylthio group, and examples of the aralkylthio group include a benzylthio group.

Examples of the alkenyl group represented by R _{71 to} R ₇₇ include vinyl group, propenyl group, 1-butenyl group, iso-butenyl group, 1-pentenyl group, 2-pentenyl group, 2-methyl-1-butenyl group, 3 Carbon number of 2-methyl-1-butenyl group, 2-methyl-2-butenyl group, 2,2-dicyanovinyl group, 2-cyano-2-methylcarboxyl vinyl group, 2-cyano-2-methylsulfonvinyl group, etc. 2-20 alkenyl groups are mentioned.

Examples of the aryl group represented by R _{71 to} R ₇₇ include a phenyl group and a naphthyl group. As the substituent of the aryl group, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkyl group, and an aryl Examples thereof include an amino group which may be 1 or 2 substituted with a substituent consisting of a group. Examples of the aryl group having a substituent include a nitrophenyl group, a nitronaphthyl group, a cyanophenyl group, a cyanonaphthyl group, a hydroxyphenyl group, a hydroxynaphthyl group, a 2-methylphenyl group, a 4-methylphenyl group, and a dimethylphenyl group. , Trimethylphenyl group, 4-i-propylphenyl group, 4-t-butylphenyl group, methylnaphthyl group, methoxyphenyl group, ethoxyphenyl group, dichlorophenyl group, trifluoromethylphenyl group, trifluoromethylnaphthyl group, N, Examples thereof include those having 6 to 20 carbon atoms such as N-dimethylaminophenyl group.

Examples of the aryl group of the aryloxy group represented by R _{71 to} R ₇₇ include the same aryl groups as those described above.
Examples of the aryl group of the arylthio group represented by R _{71 to} R ₇₇ include the same aryl groups as those described above.

Examples of the heterocyclic group represented by R _{71 to} R ₇₇ include a C 4-20 heterocyclic ring containing an oxygen atom, a nitrogen atom or a sulfur atom as a hetero atom. Specific examples include pyrrolyl group, thienyl group, furanyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, imidazolyl group, benzoxazolyl group, benzothiazolyl group, benzoimidazolyl group, benzofuranyl group, and indolyl group. Examples of these substituents include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a hydroxyl group, and a halogen atom.

Examples of the heterocyclic group of the heterocyclic oxy group represented by R _{71 to} R ₇₇ include the same heterocyclic groups as those described above.

The carbamoyl group optionally having substituents represented by R _{71 to} R ₇₇ is selected from the group consisting of an optionally substituted alkyl group and an optionally substituted aryl group. Examples thereof include an aminocarbonyl group optionally substituted by 1 or 2 substituents.
Examples of the aminocarbonyl group include alkylaminocarbonyl groups having 2 to 20 carbon atoms such as a methylaminocarbonyl group, an ethylaminocarbonyl group, an n-propylaminocarbonyl group, an n-butylaminocarbonyl group, and an n-hexylaminocarbonyl group; A dialkylaminocarbonyl group having 3 to 20 carbon atoms such as a dimethylaminocarbonyl group, a diethylaminocarbonyl group, a di-n-propylaminocarbonyl group, a di-n-butylaminocarbonyl group, an N-methyl-N-cyclohexylaminocarbonyl group; Arylaminocarbonyl groups having 7 to 20 carbon atoms such as phenylaminocarbonyl group, 4-methylphenylaminocarbonyl group, 2-methoxyphenylaminocarbonyl group, 4-n-propylphenylaminocarbonyl group; hydroxyethylaminocarbonyl group, 2 -Hydroxypropyl C2-C20 mono (hydroxyalkyl) aminocarbonyl group such as aminocarbonyl group and 3-hydroxypropylaminocarbonyl group; di (hydroxyethyl) aminocarbonyl group, di (2-hydroxypropyl) aminocarbonyl group, di ( C3-C20 di (hydroxyalkyl) aminocarbonyl group such as 3-hydroxypropyl) aminocarbonyl group; methoxymethylaminocarbonyl group, methoxyethylaminocarbonyl group, ethoxymethylaminocarbonyl group, ethoxyethylaminocarbonyl group, C1-C20 mono (alkoxyalkyl) aminocarbonyl group such as xylethylaminocarbonyl group; di (methoxyethyl) aminocarbonyl group, di (ethoxymethyl) aminocarbonyl group, di (ethoxyethyl) aminocarbo Group, di (propoxyethyl) di (alkoxyalkyl) aminocarbonyl group having 5 to 20 carbon atoms such as amino group and the like.

The metal M ₇ that forms a chelate compound together with the dipyrromethene compound represented by the general formula (VII) is not particularly limited as long as it is generally a metal having the ability to form a chelate compound with a dibenzopyromethene compound. Group 9, Group 10 (Group VIII), Group 11 (Group Ib), Group 12 (Group IIb), Group 3 (Group IIIa), Group 4 (Group IVa), Group 5 (Group Va), Group 6 ( Group VIa) and Group 7 (Group VIIa) metals, preferably transition elements such as nickel, cobalt, iron, ruthenium, rhodium, palladium, copper, osmium, iridium, platinum and zinc.
The suitable example is shown below.

  Among the compounds listed above, a more preferable compound having an absorption maximum at 480 to 520 nm is a squarylium compound represented by the general formula (VI).

  In the electronic display filter according to the present invention, the compounds represented by the general formulas (II) to (VII) of these general formulas are included in a layer different from the layer including the compound represented by the general formula (I). However, it is preferable that it is contained in the same layer as the layer containing the compound represented by formula (I) from the viewpoint of production cost and labor.

Moreover, the filter for electronic displays of this invention can provide an ultraviolet absorption layer, in order to improve light resistance.
Furthermore, the filter for electronic displays of this invention can provide a near-infrared cut layer and an electromagnetic wave cut layer. The near-infrared cut layer is installed on the front surface of the display for the purpose of preventing malfunction in remote control or transmission optical communication due to near-infrared rays emitted from the plasma display. As the electromagnetic wave cut layer, a metal oxide or the like deposited or sputtered or coated, a mesh by etching a copper foil or a copper plating layer, or the like can be used, and cuts an electromagnetic wave radiated from an electronic display.

  This filter for electronic displays can be used as a laminated body laminated with transparent glass, other transparent resin plates, etc. as well as a single one. In addition, the present invention is implemented by combining the characteristics of a plurality of members such as a member directly attached to a display surface of an electronic display, a member installed as a laminate bonded to transparent glass or another transparent resin plate, and the like. You can also In order to obtain an electronic display or a plasma display panel display device using the electronic display filter of the present invention, any known display device or commercially available display device can be used without particular limitation.

EXAMPLES Hereinafter, the present invention will be described in more detail with reference to examples. However, the present invention is not limited to the following examples unless it exceeds the gist.
<Filter evaluation method>
1. Luminous transmittance (definition JIS Z8105-1982):
Using the transmission spectrum of the filter measured by Shimadzu spectrophotometer UV3100PC, Y of the tristimulus value of the XYZ color system was calculated and used as luminous transmittance. The calculation method is based on JIS Z8722-2000.
In addition, in this calculation, the emission spectrum of the plasma display (W32-PD2100) made by Hitachi, Ltd. measured with the Minolta spectroluminance meter was used as the emission spectrum of the electronic display.
2. Contrast visual evaluation:
A filter was installed in front of the aforementioned plasma display manufactured by Hitachi, Ltd., and the contrast was visually evaluated in a state where white was displayed at the center of the display and nothing was displayed around the display (no display light emission). The evaluation was performed in a room in which a three-wavelength light emitting daylight fluorescent lamp was installed on the ceiling.

(Example 1)
To a polyethylene terephthalate film (PET film “A7300” manufactured by Toyobo Co., Ltd., thickness 125 μm), dimethylethane (DME) solution (resin content 30 wt%) of polymethyl methacrylate resin (“Dianal BR-80” manufactured by Mitsubishi Rayon Co., Ltd.) The compounds shown in the table below, dimethoxyethane, and toluene were mixed and dissolved, and the resulting solution was treated with NO. It was coated and dried with a 12 bar coater (manufactured by Tester Sangyo Co., Ltd.) to obtain a filter having a coating film having a thickness of 4.5 μm. This is film A.

  Polyethylene terephthalate film (Mitsubishi Chemical Polyester Film Co., Ltd. PET film “T600E W07”, thickness 50 μm) has an alicyclic alkyl methacrylate resin (“Optretz OZ-1100” manufactured by Hitachi Chemical Co., Ltd.) 35 wt%, methyl ethyl ketone (MEK) 32.5 wt%, toluene 32.5 wt%, diimonium-based near-infrared absorbing dye (N, N, N ', N',-tetrakis (p-dibutylylaminophenyl) -p-phenylene Diimonium hexafluoride antimonate) 9.4% / resin content, toluene and MEK are mixed and dissolved, and the resulting solution is coated with an N0.10 bar coater (manufactured by Tayu Kikai Co., Ltd.) and dried to form a film. A coating film having a thickness of 3.0 μm was formed. On the other side of this film, an alicyclic alkyl methacrylate resin ("Optretz OZ-1100" manufactured by Hitachi Chemical Co., Ltd.) 35 wt% resin, methyl ethyl ketone (MEK) 32.5 wt%, toluene 32.5 wt% Aminothiol nickel complex near infrared absorbing dye {bis-2,2 ′-[1,2-di (3-chlorophenyl) ethylenediimine] benzenethiolate} nickel (II) 5.0 wt% / resin content, toluene, MEK was mixed and dissolved, and a coating film was similarly formed using the obtained solution to obtain a film B.

  The above-mentioned film B, film A, electromagnetic wave shielding mesh (line width: 10 μm, line pitch: 250 μm), glass, and antireflection film (Nihon Yushi Co., Ltd. Realak 8201UV) were sequentially bonded to obtain a filter for electronic display.

Light transmittance Y ² (%) at the green emission peak (usually 545 nm) of the three-wavelength fluorescent tube of this filter and light transmittance Y ⁴ (%) at the wavelength of the green emission peak of the display (usually 525 nm) The luminous transmittance Y ¹ (%) using the white emission spectrum of the plasma display and the luminous transmittance Y ³ (%) using the emission spectrum of the three-wavelength fluorescent lamp F10 were evaluated. Each evaluation result is shown in Table-2.
Moreover, the visual evaluation of the contrast of this filter was performed. The results are summarized at the end.

得られたフィルターは、実施例１と同様に評価を行った。結果を表−２に示す。 (Example 2)
A filter for electronic display was obtained in the same manner as in Example 1 except that the compounds shown in the following table were used for the production of Film A.

The obtained filter was evaluated in the same manner as in Example 1. The results are shown in Table-2.

得られたフィルターは、実施例１と同様に評価を行った。結果を表−２に示す。 (Example 3)
A filter for electronic display was obtained in the same manner as in Example 1 except that the compounds shown in the following table were used for the production of Film A.

The obtained filter was evaluated in the same manner as in Example 1. The results are shown in Table-2.

得られたフィルターは、実施例１と同様に評価を行った。結果を表−２に示す。 Example 4
A filter for electronic display was obtained in the same manner as in Example 1 except that the compounds shown in the following table were used for the production of Film A.

The obtained filter was evaluated in the same manner as in Example 1. The results are shown in Table-2.

得られたフィルターは、実施例１と同様に評価を行った。結果を表−２に示す。 (Example 5)
A filter for electronic display was obtained in the same manner as in Example 1 except that the compounds shown in the following table were used for the production of Film A.

The obtained filter was evaluated in the same manner as in Example 1. The results are shown in Table-2.

得られたフィルターは、実施例１と同様に評価を行った。結果を表−２に示す。また、このフィルターの透過率スペクトルを図２に、このフィルターを透過した後の３波長域発光形蛍光灯の発光スペクトル及びこのフィルターを透過した後のプラズマディスプレイ発光スペクトルを図４に示す。 (Example 6)
A filter for electronic display was obtained in the same manner as in Example 1 except that the compounds shown in the following table were used for the production of Film A.

The obtained filter was evaluated in the same manner as in Example 1. The results are shown in Table-2. FIG. 2 shows the transmittance spectrum of this filter, and FIG. 4 shows the emission spectrum of the three-wavelength region fluorescent lamp after passing through this filter and the plasma display emission spectrum after passing through this filter.

(Comparative Example 1)
A filter for electronic display was obtained in the same manner as in Example 1 except that the compounds shown in the following table were used for the production of Film A.

  The obtained filter was evaluated in the same manner as in Example 1. The results are shown in Table-2.

Contrast visual evaluation:
In Examples 1 to 6, the contrast was felt high.
In Comparative Example 1, the external light (indoor fluorescent lamp) was strongly reflected in the portion where light was not emitted, so that the black became whitish and the contrast was felt to be the lowest.

From the evaluation results shown in Table 2, the light transmittance Y ² (%) at the green emission peak of the three-wavelength region emission fluorescent tube of each of the filters obtained in Examples 1 to 6 is the green emission peak of the display. light transmittance Y ⁴ at the wavelength of the (%) 10 or more lower than the further luminous transmittance using 3 emission spectrum of band fluorescent lamp F10 Y ³ (%) is used the emission spectrum of the plasma display Since the luminous transmittance Y ¹ (%) is two or more, it is considered that Examples 1 to 6 have high contrast. In Comparative Example 1, [Y ⁴ (%) − Y ² (%)] is 5 or less, and [Y ¹ (%) − Y ³ (%)] is 0 or less. Is not considered high.

Arrangement explanatory drawing which conceptually shows the state where the filter for electronic display of the present invention is arranged in front of the electronic display and the reflected light of the external light on the surface of the electronic display is reduced without impeding the light emission of the electronic display It is. It is a characteristic view which shows the emission spectrum of the electronic display which consists of a plasma display, the emission spectrum of 3 wavelength range light emission type fluorescent lamp F10, and the transmission spectrum of the filter for electronic displays of this invention mentioned in Example 6. FIG. It is a characteristic view which shows the emission spectrum of the electronic display which consists of a plasma display, and the emission spectrum of the 3 wavelength range light emission type fluorescent lamp F10. It is a characteristic view which shows the emission spectrum of the plasma display after permeate | transmitting the filter for electronic displays of this invention quoted in Example 6, and the emission spectrum of the 3 wavelength range light emission type fluorescent lamp F10.

Explanation of symbols

3 External light 10 that has passed through the electronic display filter twice and unnecessary components have been cut off 10 Electronic display filter 11 Electronic display 12 Emission light 13 of the electronic display External light that has passed through the electronic display filter and its reflected light 14 Emission spectrum of electronic display emission 15 Emission spectrum of three-wavelength fluorescent lamp F10 16 Transmission spectrum of filter for electronic display 23 External light G Green emission portion R1 of plasma display Red emission portion R2 of plasma display Red of plasma display Light emitting part B Blue light emitting part of plasma display

Claims (5)

A filter for electronic displays, comprising a layer containing a dipyrromethene dye having an absorption maximum at 530 to 560 nm. The filter for electronic displays according to claim 1, wherein the dipyrromethene dye is a compound represented by the following general formula (I).

[In the formula (I), R _{11 to} R ₁₉ are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group which may have a substituent, or an esterified group. Carboxyl group, sulfonic acid group, acyl group, acyloxy group, alkyl group optionally having substituent, alkoxy group optionally having substituent, alkylthio group optionally having substituent, substituted An alkenyl group which may have a group, an aryl group which may have a substituent, an aryloxy group which may have a substituent, an arylthio group which may have a substituent, a substituent A heterocyclic group optionally having a heterocyclic oxy group optionally having a substituent,
It represents a carbamoyl group which may have a substituent, and M ₁ represents a transition metal atom. ] The filter for electronic displays according to claim 1 or 2, further comprising a layer containing a compound represented by the following general formula (II), (III) or (IV).

[In formula (II), R ₂₁ To R ₂₈ each independently represents a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an amino group which may have a substituent alkyl group, alkoxy group which may have a substituent, An aryl group which may have a substituent, an aryloxy group which may have a substituent, an alkylamino group which may have a substituent, a dialkylamino group which may have a substituent , An optionally substituted alkylthio group, or an optionally substituted arylthio group, R ₂₁ and R ₂₂ , R ₂₃ and R ₂₄ , R ₂₅ and R ₂₆ , R ₂₇ And R ₂₈ may be linked to each other to form an aliphatic carbocycle. M ₂ represents two hydrogen atoms, a divalent metal atom, a trivalent monosubstituted metal atom, a tetravalent disubstituted metal atom or an oxymetal atom. ]

[In Formula (III), each R ₃₁ independently represents an alkyl group which may have a substituent, an alkoxy group which may have a substituent, or an cycloalkyl which may have a substituent. group, an optionally substituted aryl group, an optionally substituted aryl group, or a halogen atom, W ₃ -X ₃ W ₃ in the -R ₃₂ are each independently , An imino group, an alkylimino group, or an oxygen atom, each of X ₃ independently represents a carbonyl group or a sulfonyl group, each of R ₃₂ independently represents a monovalent group or a hydrogen atom, ₃ and l ₃ ′ are each independently an integer of 0 to 5, m ₃ and m ₃ ′ are each independently an integer of 0 to 5, n ₃ and n ₃ ′ are n ₃ + n ₃ ′ ≧ 1 in -3 _{integer, l 3 + m 3 + n} 3 ≦ 5, and l '+ m' + n 'is ≦ 5, R ₃₁ and W ₃ on the benzene ring - _{When 3} -R ₃₂ are a plurality each occurrence, each of R ₃₁ and W ₃ -X ₃ -R _32, in one benzene ring, and in between the other benzene rings, may be different from each other . ]

[(In the formula (IV), -T ₄ - are each independently an oxygen atom, a sulfur atom, or, -CR ₄₁ R ₄₂ - independently of the group (R ₄₁ and R ₄₂ represented by the number of carbon atoms represents 1-4 alkyl group, R ₄₁ and R ₄₂ are oxygen connected, sulfur, nitrogen atom may also form a good 3-6 membered ring include.), and, Y ₄ are each independently X ₄ represents each independently a hydrogen atom, a halogen atom, an alkyl group, or an aryl group, and R ₄₀ each independently represents a halogen atom, a nitro group, an alkoxy group, or an aryl group. ^{Represents a} group, k ₄ represents 1 or 2, An ₄ m ⁴⁻ represents an m ₄ valent anion, m ₄ represents an integer of 1 or 2, and p ₄ represents a coefficient for keeping the charge neutral. .] It has a layer containing the compound represented with the following general formula (V), The filter for electronic displays in any one of Claims 1-3 characterized by the above-mentioned.

[In Formula (V), R ₅₃ represents an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an aryl group which may have a substituent, or hydrogen. R ₅₁ represents each independently an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an alkoxycarbonyl group which may have a substituent, a substituent A cycloalkyl group which may have a group, an aryl group which may have a substituent, an aryloxy group which may have a substituent, an aryloxycarbonyl group which may have a substituent Represents an optionally substituted amino group or a hydrogen atom, and each R ₅₂ independently represents an optionally substituted alkyl group or an optionally substituted cycloalkyl. Group, aryl group optionally having substituent (s), or hydrogen Shows the child, Y ₅ each independently represents an oxygen atom, or an imino group, these R _51, R _52, and Y ₅ may be different from each other between both of the pyrazole ring. ] It has a layer containing the compound represented by the following general formula (VI) or (VII), The filter for electronic displays in any one of Claims 1-4 characterized by the above-mentioned.

[In Formula (VI), each R ₆₁ is independently an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, or an aryl which may have a substituent. R ₆₂ represents a group or a hydrogen atom, and each R ₆₂ independently represents an alkyl group which may have a substituent, an alkoxy group which may have a substituent, or an alkoxy which may have a substituent. Carbonyl group, optionally substituted cycloalkyl group, optionally substituted aryl group, optionally substituted aryloxy group, optionally substituted An aryloxycarbonyl group, an amino group which may have a substituent, a hydroxyl group, or a hydrogen atom is shown, and these R ₆₁ and R ₆₂ may be different from each other between both pyrazole rings. ]

Wherein (VII), each independently R ₇₁ to R _77, a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxyl group, an optionally substituted amino group, it may be esterified Carboxyl group, sulfonic acid group, acyl group, acyloxy group, alkyl group optionally having substituent, alkoxy group optionally having substituent, alkylthio group optionally having substituent, substituted An alkenyl group which may have a group, an aryl group which may have a substituent, an aryloxy group which may have a substituent, an arylthio group which may have a substituent, a substituent Represents a heterocyclic group optionally having a substituent, a heterocyclic oxy group optionally having a substituent, and a carbamoyl group optionally having a substituent, and R ₇₁ and R ₇₂ or R ₇₆ and R _77. Each may be linked and have a substituent. An aromatic ring may be formed. M ₇ represents a metal atom. ]

Images