JP2012032630A - Optical filter - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an optical filter having excellent optical characteristics (for instance, absorption characteristics of light and narrow half-value width) and durability.SOLUTION: In the optical filter containing at least one kind of a neodymium complex of a calixarene derivative, the neodymium complex of the calixarene derivative is at least one kind of compound selected from the following general formula (1) and general formula (2).

Description

  The present invention relates to an optical filter. More specifically, the present invention relates to an optical filter containing at least one neodymium complex of calixarene derivative. Further, the present invention relates to a display filter such as a plasma display panel (PDP) and a liquid crystal display (LCD) containing the compound, and a spectacle lens filter.

  In recent years, various functional materials have been actively developed in various fields such as optoelectronics-related applications accompanying the advancement of information technology in society. For example, as the organic material, cyanine dyes, polymethine dyes, squarylium dyes, tetraazaporphyrin dyes, metal dithiol complex dyes, phthalocyanine dyes, diimonium dyes or inorganic oxide particles are used. Among them, tetraazaporphyrin compounds having specific substituents have absorption maximums in the wavelength range of 570 to 605 nm, and are therefore widely used in various display filters such as liquid crystal displays, plasma displays, and organic electroluminescent elements (Patent Documents). 1-4).

On the other hand, eyeglass lenses are required to reduce discomfort associated with glare for visible light, blurring of contrast, and visual fatigue. As one of the countermeasures, as a rare earth metal compound as a lens material, neodymium compound A method of blending is frequently used (Patent Document 5).
In general, when a compound that selectively absorbs a specific wavelength is applied to, for example, a display filter for a plasma display or a liquid crystal display, the compound is contained in the polymer film, A method of applying to one side or both sides is applied. In addition, a method in which a compound that selectively absorbs a specific wavelength is contained in an adhesive layer used when laminating a plurality of polymer films. When producing such a filter for display, the compound itself that selectively absorbs a specific wavelength needs characteristics such as solubility in an organic solvent. In addition, when the display filter is used by being mounted on an actual display, durability (for example, light resistance and wet heat resistance) is required. From such a demand, the durability of the compound itself is also demanded for a compound that selectively absorbs a specific wavelength.
In addition, when applied to a spectacle lens filter, it has a high transmittance in a wavelength band necessary for visibility, and in a wavelength band that adversely affects glare, it absorbs light of that wavelength. It is necessary to have both visibility and visibility. Therefore, the compound needs to have a characteristic that the peak of the absorption spectrum in the absorption wavelength band is extremely sharp.

From such points, the compounds having a specific structure described in Patent Documents 1 to 4 have characteristics required for display filter applications, such as solubility in organic solvents and durability (light resistance). Although it has certain characteristics, at present, further durability (for example, resistance to moist heat) and further optical characteristics (narrow width at half maximum) are demanded. Furthermore, although the neodymium compound described in Patent Document 5 has a very sharp absorption peak near 585 nm, it has a problem in solubility depending on the type of filter material.
A calixarene compound is a molecule having a conical structure formed by cyclic condensation of phenol and formaldehyde, and is known to include various compounds (Non-Patent Document 1) and binds to a metal ion. Many attempts have been made because it has a phenolic hydroxyl group and an aromatic ring that creates a cavity for taking in hydrophobic guests. For example, it has been proposed to extract alkali or alkaline earth metal ions by introducing phosphine oxide into a hydroxyl group (Patent Document 6). However, until now, there has been no report regarding the application of calixarene compounds to optical filters.

JP 2002-251144 A JP 2002-40233 A JP 2000-275432 A JP 2008-268331 A JP 2000-75128 A Special Table 2002-540064

Royal Society of Chemistry, Cambridge, 1989

An object of the present invention is to provide an optical filter. More specifically, the present invention provides an optical filter excellent in optical characteristics (for example, light absorption characteristics, narrow half-value width) and durability (for example, moisture and heat resistance), comprising a neodymium complex of calixarene derivative. That is.

As a result of earnest studies on the optical filter, the present inventors have completed the present invention. That is, the present invention
(I) An optical filter comprising at least one neodymium complex of calixarene derivative,
(Ii) The optical filter of (i) above, wherein the neodymium complex of the calixarene derivative is at least one compound selected from the following general formula (1) and general formula (2).
[Wherein R 1 represents a linear or branched alkyl group, R 2 represents a linear or branched alkyl group or a linear or branched halogenoalkyl group, and X represents a halogen atom or a linear or branched alkoxy group. Represents)

[Wherein R3 represents a linear or branched alkyl group, R4 represents a nitrogen-containing aromatic heterocyclic group, Y represents an anion, and n represents an integer of 1 or 2]
further,
(Iii) R1 in the general formula (1) or R3 in the general formula (2) is a tert-butyl group,
(Iv) a display using any one of the optical filters (i) to (iii), and (v) a spectacle lens using any one of the optical filters (i) to (iii). is there.

According to the present invention, it has become possible to provide an optical filter having excellent optical properties and durability, comprising a novel calixarene derivative neodymium complex.

It is typical sectional drawing of the optical filter of this invention. It is typical sectional drawing of the optical filter of this invention. It is typical sectional drawing of the optical filter of this invention. It is typical sectional drawing of the optical filter of this invention. It is typical sectional drawing of the optical filter of this invention. It is typical sectional drawing of the optical filter of this invention. It is typical sectional drawing of the optical filter of this invention.

Hereinafter, the present invention will be described in detail.
<Neodymium complex of calixarene derivative of the present invention>
The present invention relates to a display comprising at least one neodymium complex of a calixarene derivative in which neodymium is introduced into a phenolic hydroxyl group having a substituent constituting calixarene (hereinafter abbreviated as compound A according to the present invention). The present invention also relates to a filter for eyeglasses, a display device comprising the filter, and a filter for glasses comprising at least one of the compounds.
The compound A according to the present invention is a compound in which an aromatic ring constituting a calixarene has, for example, an alkyl group or a halogenoalkyl group as a substituent, and a phenolic hydroxyl group is bonded to neodymium, and has excellent optical properties. It has characteristics (for example, light absorption characteristics, narrow half width), and excellent durability. An optical filter containing a neodymium complex of calixarene derivative having such characteristics has excellent optical characteristics and excellent durability.
The compound A according to the present invention is preferably a compound represented by at least one selected from the general formula (1) to the general formula (2).

[Wherein R 1 represents a linear or branched alkyl group, R 2 represents a linear or branched alkyl group or a linear or branched halogenoalkyl group, and X represents a halogen atom or a linear or branched alkoxy group. Represents)
[Wherein R3 represents a linear or branched alkyl group, R4 represents a nitrogen-containing aromatic heterocyclic group, Y represents an anion, and n represents an integer of 1 or 2]

<Compound of general formula (1)>
In the compound represented by the general formula (1), R1 preferably represents a linear or branched alkyl group having 1 to 12 carbon atoms.
In the formula represented by the general formula (1), R1 represents that the phenolic hydroxyl group constituting the calixarene is substituted with a carbon atom at the meta or para position of the benzene ring, and more preferably. Is a substitution at a carbon atom in the para position.
Specific examples of R1 in the general formula (1) include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n- Pentyl group, isopentyl group, neopentyl group, tert-pentyl group, 1,2-dimethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4 -Methylpentyl group, 4-methyl-2-pentyl group, 1,2-dimethylbutyl group, 2,3-dimethylbutyl group, 3,3-dimethylbutyl group, 1-ethylbutyl group, 2-ethylbutyl group, n- Heptyl group, 1-methylhexyl group, 3-methylhexyl group, 5-methylhexyl group, 2,4-dimethylpentyl group, cyclohexylmethyl N-octyl group, tert-octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, 2,5-dimethylhexyl group, 2,5,5-trimethylhexyl group, n-nonyl group 2,2-dimethylheptyl group, 2,6-dimethyl-4-heptyl group, 3,5,5-trimethylhexyl group, n-decyl group, 4-ethyloctyl group, n-undecyl group, 1-methyldecyl group And linear or branched alkyl groups such as n-dodecyl group and 1,3,5,7-tetramethyloctyl group.
In the compound represented by the general formula (1), more preferably, R1 represents a linear or branched alkyl group having 1 to 8 carbon atoms, and more preferably a linear or branched alkyl group having 1 to 4 carbon atoms. Represents an alkyl group, particularly preferably a tert-butyl group.
In the compound represented by the general formula (1), R2 preferably represents a linear or branched alkyl group having 1 to 12 carbon atoms or a linear or branched halogenoalkyl group having 1 to 12 carbon atoms.
As specific examples of R2 in the general formula (1), linear or branched alkyl groups having 1 to 12 carbon atoms, fluoromethyl groups, 3-fluoropropyl groups, 6 -Fluorohexyl group, 8-fluorooctyl group, trifluoromethyl group, 1,1-dihydro-perfluoroethyl group, 1,1-dihydro-perfluoro-n-propyl group, 1,1,3-trihydro-per Fluoro-n-propyl group, 2-hydro-perfluoro-2-propyl group, 1,1-dihydro-perfluoro-n-butyl group, 1,1-dihydro-perfluoro-n-pentyl group, 1,1 -Dihydro-perfluoro-n-hexyl group, 6-fluorohexyl group, 1,1-dihydro-perfluoro-n-octyl group, 1,1-dihydro-perfluoro -N-dodecyl group, perfluoro-n-hexyl group, 2,2-bis (trifluoromethyl) propyl group, dichloromethyl group, 2-chloroethyl group, 3-chloropropyl group, 4-chlorocyclohexyl group, 7- Examples thereof include linear or branched halogenoalkyl groups such as chloroheptyl group, 8-chlorooctyl group, and 2,2,2-trichloroethyl group.

In the compound represented by the general formula (1), more preferably, R2 represents a linear or branched alkyl group having 1 to 8 carbon atoms or a linear or branched halogenoalkyl group having 1 to 8 carbon atoms.
In the compound represented by the general formula (1), more preferably, R1 represents a linear or branched alkyl group having 1 to 4 carbon atoms or a linear or branched halogenoalkyl group having 1 to 4 carbon atoms.
In the compound represented by the general formula (1), X represents a halogen atom or a linear or branched alkoxy group having 1 to 12 carbon atoms.
Specific examples of X in the general formula (1) include, for example, a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom,
For example, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, cyclopentyloxy group, n-hexyloxy group 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, cyclohexyloxy group, n-heptyloxy group, n-octyloxy group, 2-ethylhexyloxy group, n-nonyloxy group, n-decyloxy group, n Examples thereof include linear or branched alkoxy groups such as -undecyloxy group and n-dodecyloxy group.

In the compound represented by the general formula (1), more preferably, X represents a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a linear or branched alkoxy group having 1 to 8 carbon atoms, and more preferably. , A fluorine atom, a chlorine atom, a linear or branched alkoxy group having 1 to 4 carbon atoms.
Specific examples of the compound represented by the general formula (1) according to the present invention include the following compounds, but the present invention is not limited thereto.

<Method for producing compound of general formula (1)>
The compound represented by the general formula (1) according to the present invention can be produced by various organic chemical methods.

For example, first, a calix [4] arene of a cyclic tetramer represented by the general formula (3) (for example, it can be produced according to J. Am. Chem. Soc., 103, 3782 (1981)), A precursor compound represented by the general formula (4) is produced using an alkyl compound or halogenoalkyl compound having a leaving group represented by the general formula (5) in the presence of a base, preferably using a solvent [for example, And can be produced according to the method described in Tetrahedron Letters, 30, 2681 (1989)].
[In General Formula (3) to General Formula (5), R1 and R2 have the same meaning as in General Formula (1), and Z represents a leaving group.]
In the compound represented by the general formula (5), Z represents a leaving group, preferably a halogen atom or a p-toluenesulfonyl group. The halogen atom which is a preferable leaving group represented by Z represents a chlorine atom, a bromine atom or an iodine atom, and more preferably a bromine atom or an iodine atom.
The amount of the compound represented by the general formula (5) is not particularly limited, and is generally 2.0 with respect to the calix [4] arene of the cyclic tetramer represented by the general formula (3). It is preferable to use about -7.0 mol, and it is more preferable to use about 3.0-6.0 mol.
The solvent is not particularly limited as long as it does not inhibit this reaction. For example, aromatic hydrocarbons such as benzene, toluene, xylene, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, chloroform, dichloromethane, etc. Halogenated hydrocarbons, esters such as methyl acetate and ethyl acetate, ethers such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, Examples thereof include amides such as 1,3-dimethyl-2-imidazolidinone, acetonitrile, dimethyl sulfoxide, pyridine and the like.
These solvents are appropriately selected according to the ease of reaction, and can be used singly or in combination of two or more. If necessary, water may be removed with a suitable dehydrating agent or desiccant and used as a non-aqueous solvent.
In the case of using a solvent, generally, when the amount of the solvent increases, the efficiency of the reaction decreases. On the other hand, when the amount of the solvent decreases, it becomes difficult to uniformly heat and stir or a side reaction tends to occur. Therefore, it is desirable that the amount of the solvent is up to 100 times, preferably 5 to 50 times that of the whole intermediate compound by weight ratio.

Examples of the base include alkali metal hydrides such as sodium hydride, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, alkalis such as sodium hydrogen carbonate, sodium carbonate, potassium carbonate and cesium carbonate. Examples thereof include organic bases such as metal carbonates, pyridine, and triethylamine.
What is necessary is just to select the usage-amount of a base suitably in the range of 0.5-10.0 times mole with respect to the compound represented by General formula (5).
The reaction temperature may be appropriately selected in the range of 0 to 200 ° C., but is preferably in the range of room temperature to solvent reflux temperature.
The reaction time is not constant depending on the reaction scale and reaction temperature, but may be appropriately selected within the range of 1 to 48 hours.
When a solvent that dissolves in water is used after completion of the reaction, the reaction solution is discharged into water, and the precipitate is filtered off and washed with methanol. When a solvent insoluble in water is used, the solvent is distilled off under reduced pressure, water is added, the precipitate is filtered off and washed with methanol. If necessary, the precipitate can be purified by a method such as recrystallization.

Next, by incorporating the compound represented by the general formula (4) and the neodymium compound represented by the general formula (6) in the presence of a base, preferably using a solvent, the general formula according to the present invention. The compound represented by (1) can be produced.
[In General Formula (4) and General Formula (6), R 1, R 2 and X represent the same meaning as in General Formula (1)]

The solvent for the inclusion reaction is not particularly limited as long as it does not inhibit this reaction. For example, hydrocarbons such as pentane, hexane, cyclohexane, octane, benzene, toluene, xylene, carbon tetrachloride, chloroform, 1 , 2-dichloroethane, 1,2-dibromoethane, trichloroethylene, tetrachloroethylene, chlorobenzene, bromobenzene, α-dichlorobenzene and other halides, methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, Isobutyl alcohol, isopentyl alcohol, cyclohexanol, ethylene glycol, propylene glycol, 2-methoxyethanol, 2-ethoxyethanol, phenol, benzyl alcohol, cresol, diethylene glycol Alcohols and phenols such as coal, triethylene glycol, glycerin, diethyl ether, diisopropyl ether, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, anisole, 1,2-dimethoxyethane, diethylene glycol dimethyl ether, dicyclohexyl-18-crown 6. Examples include ethers such as methyl carbitol and ethyl carbitol, nitriles such as acetonitrile, propionitrile, succinonitrile, and benzonitrile, nitro compounds such as nitromethane and nitrobenzene, and sulfur-containing compounds such as dimethyl sulfoxide and sulfolane. be able to.

These solvents are appropriately selected according to the ease of reaction, and can be used singly or in combination of two or more. If necessary, water may be removed with a suitable dehydrating agent or desiccant and used as a non-aqueous solvent.
In the case of using a solvent, generally, when the amount of the solvent increases, the efficiency of the reaction decreases. On the other hand, when the amount of the solvent decreases, it becomes difficult to uniformly heat and stir or a side reaction tends to occur. Therefore, it is desirable that the amount of the solvent is up to 100 times, preferably 5 to 50 times that of the whole compound represented by the general formula (4) by weight.
Examples of the base include sodium, potassium, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, sodium carbonate, ammonia, triethylamine, piperidine, pyridine, pyrrolidine, aniline, N, N-dimethylaniline, N, N-diethylaniline and the like can be mentioned.
What is necessary is just to select the usage-amount of a base suitably in the range of 1-10 times mole with respect to the compound represented by General formula (4).
The reaction temperature may be appropriately selected in the range of 0 to 200 ° C., but is preferably in the range of room temperature to solvent reflux temperature.
The reaction time is not constant depending on the reaction scale and reaction temperature, but may be appropriately selected within the range of 1 to 48 hours.
When a solvent that dissolves in water is used after completion of the reaction, the reaction solution is discharged into water, and the precipitate is filtered off and washed with water. When a solvent insoluble in water is used, the solvent is distilled off under reduced pressure, water is added, the precipitate is filtered off and washed with water. If necessary, the precipitate can be purified by a method such as recrystallization.

<Compound of general formula (2)>
In the compound represented by the general formula (2), R3 preferably represents a linear or branched alkyl group having 1 to 12 carbon atoms.
In the formula represented by the general formula (2), R3 represents that the phenolic hydroxyl group constituting the calixarene is substituted with a carbon atom at the meta or para position of the benzene ring, and more preferably. Is a substitution at a carbon atom in the para position.
Specific examples of R3 in the general formula (2) include the linear or branched alkyl groups exemplified for R1 in the compound represented by the general formula (1).
In the compound represented by the general formula (2), more preferably, R3 represents a linear or branched alkyl group having 1 to 8 carbon atoms, and more preferably a linear or branched alkyl group having 1 to 4 carbon atoms. Represents an alkyl group, particularly preferably a tert-butyl group.
In the compound represented by the general formula (2), R4 preferably represents an unsubstituted nitrogen-containing aromatic heterocyclic group.
Specific examples of R4 in the general formula (2) include 8-quinolinyl group, 7-quinolinyl group, 5-quinolinyl group, 4-quinolinyl group, 3-quinolinyl group, 2-quinolinyl group, 8-isoquinolinyl group, 7 -Isoquinolinyl group, 5-isoquinolinyl group, 4-isoquinolinyl group, 4-pyridinyl group, 3-pyridinyl group, 2-pyridinyl can be mentioned.
In the compound represented by the general formula (2), more preferably, R4 represents an 8-quinolinyl group, a 7-quinolinyl group, an 8-isoquinolinyl group, a 7-isoquinolinyl group, a 4-pyridinyl group, or 2-pyridinyl.

In the compound represented by the general formula (2), Y represents an anion, which is an organic acid anion or an inorganic anion.
Examples of the organic acid anion represented by Y include, for example, acetate ion, lactate ion, trifluoroacetate ion, propionate ion, benzoate ion, oxalate ion, succinate ion, and stearic acid. ion. Organic sulfonate ions include methanesulfonate ion, toluenesulfonate ion, naphthalene monosulfonate ion, naphthalene disulfonate ion, chlorobenzenesulfonate ion, nitrobenzenesulfonate ion, dodecylbenzenesulfonate ion, benzenesulfonate ion, ethane Sulfonate ion and trifluoromethanesulfonate ion. Examples of organic borate ions include tetraphenylborate ions and butyltriphenylborate ions.
Examples of the inorganic anion represented by Y include a fluorine ion, a chlorine ion, a bromine ion, and an iodine ion as a halogen ion. Furthermore, thiocyanate ion, hexafluoroantimonate ion, perchlorate ion, periodate ion, nitrate ion, tetrafluoroborate ion, hexafluorophosphate ion, molybdate ion, tungstate ion, titanate ion, vanadine An acid ion, a phosphate ion, a borate ion, etc. are mentioned.
In the compound represented by the general formula (2), more preferably, Y is perchlorate ion, toluenesulfonate ion, tetrafluoroborate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfone. Represents an acid ion.

In the compound represented by the general formula (2), n represents an integer of 1 or 2, and preferably n is 2.
Specific examples of the compound represented by the general formula (2) according to the present invention include the following compounds, but the present invention is not limited thereto.

<Method for producing compound of general formula (2)>
The compound represented by the general formula (2) according to the present invention can be produced by various organic chemical methods.
For example, first, the calix [4] arene of the cyclic tetramer represented by the general formula (7) (for example, it can be produced according to J. Am. Chem. Soc., 103, 3782 (1981)), A compound having a leaving group represented by the following general formula (8) is produced in the presence of a base, preferably using a solvent, to produce a precursor compound represented by the general formula (9) [for example, Chinese Chemical Letters , 8, 685 (1997)].
[In General Formula (7) to General Formula (9), R3 and R4 represent the same meaning as in General Formula (2), and Z represents a leaving group.]

In the compound represented by the general formula (8), Z represents a leaving group, preferably a halogen atom or a p-toluenesulfonyl group. The halogen atom which is a preferable leaving group represented by Z represents a chlorine atom, a bromine atom or an iodine atom, and more preferably a bromine atom or an iodine atom.
The amount of the compound represented by the general formula (8) is not particularly limited, and is generally 2.0% with respect to the calix [4] arene of the cyclic tetramer represented by the general formula (7). It is preferable to use about -7.0 mol, and it is more preferable to use about 3.0-6.0 mol.
The solvent is not particularly limited as long as it does not inhibit this reaction, and examples thereof include the solvents exemplified in the method for producing the precursor compound represented by the general formula (4).
These solvents are appropriately selected according to the ease of reaction, and can be used singly or in combination of two or more. If necessary, water may be removed with a suitable dehydrating agent or desiccant and used as a non-aqueous solvent.
In the case of using a solvent, generally, when the amount of the solvent increases, the efficiency of the reaction decreases. On the other hand, when the amount of the solvent decreases, it becomes difficult to uniformly heat and stir or a side reaction tends to occur. Therefore, it is desirable that the amount of the solvent is up to 100 times, preferably 5 to 50 times that of the whole intermediate compound by weight ratio.
As such a base, the base illustrated by the manufacturing method of the precursor compound represented by General formula (4) can be illustrated, for example.
What is necessary is just to select the usage-amount of a base suitably in the range of 0.5-10.0 times mole with respect to the compound represented by General formula (5).
The reaction temperature may be appropriately selected in the range of 0 to 200 ° C., but is preferably in the range of room temperature to solvent reflux temperature.
The reaction time is not constant depending on the reaction scale and reaction temperature, but may be appropriately selected within the range of 1 to 48 hours.
When a solvent that dissolves in water is used after completion of the reaction, the reaction solution is discharged into water, and the precipitate is filtered off and washed with methanol. When a solvent insoluble in water is used, the solvent is distilled off under reduced pressure, water is added, the precipitate is filtered off and washed with methanol. If necessary, the precipitate can be purified by a method such as recrystallization.

Next, by incorporating the compound represented by the general formula (9) and the neodymium compound represented by the general formula (10) in the presence of a base, preferably using a solvent, the general formula according to the present invention. The compound represented by (2) can be produced.
[In General Formula (9) to General Formula (10), R3, R4 and Y represent the same meaning as in General Formula (2)]
The solvent related to the inclusion reaction is not particularly limited as long as it does not inhibit this reaction, and examples thereof include the solvents exemplified in the method for producing the compound represented by the general formula (1).
These solvents are appropriately selected according to the ease of reaction, and can be used singly or in combination of two or more. If necessary, water may be removed with a suitable dehydrating agent or desiccant and used as a non-aqueous solvent.
In the case of using a solvent, generally, when the amount of the solvent increases, the efficiency of the reaction decreases. On the other hand, when the amount of the solvent decreases, it becomes difficult to uniformly heat and stir or a side reaction tends to occur. Therefore, it is desirable that the amount of the solvent is up to 100 times, preferably 5 to 50 times that of the whole compound represented by the general formula (9) by weight.
As such a base, the base illustrated by the manufacturing method of the compound represented by General formula (1) can be mentioned, for example.
What is necessary is just to select the usage-amount of a base suitably in the range of 1-10 times mole with respect to the compound represented by General formula (9).
The reaction temperature may be appropriately selected in the range of 0 to 200 ° C., but is preferably in the range of room temperature to solvent reflux temperature.
The reaction time is not constant depending on the reaction scale and reaction temperature, but may be appropriately selected within the range of 1 to 48 hours.
When a solvent that dissolves in water is used after completion of the reaction, the reaction solution is discharged into water, and the precipitate is filtered off and washed with water. When a solvent insoluble in water is used, the solvent is distilled off under reduced pressure, water is added, the precipitate is filtered off and washed with water. If necessary, the precipitate can be purified by a method such as recrystallization.

The compound A according to the present invention can be used for various functional material applications (for example, optical filter applications, optical recording medium applications, ink applications, thermal transfer applications, eyeglass filter applications). One kind may be used alone or a plurality may be used in combination.
Next, an optical filter comprising at least one neodymium complex of the calixarene derivative of the present invention will be specifically described.

<Filter for display>
The display filter of the present invention includes, for example, a plasma display, a liquid crystal display, an organic electroluminescence display, an FED (Field Emission Display), and a CRT (Cathode Ray).
This is a filter applicable to various displays such as Tube) and is used by being mounted on various displays. In addition, in a liquid crystal display, it can apply to various aspects, such as a transmission type and a reflection type, for example.
The display filter of the present invention functions as a light control film having a characteristic of correcting the visible light spectrum of the display screen by containing at least one compound A according to the present invention.
Further, the display filter of the present invention further functions as an electromagnetic wave shield having a characteristic of blocking electromagnetic waves from the display screen by providing a transparent conductive layer having a surface resistance of 0.01 to 30Ω / □. The display filter of the present invention further functions as a near-infrared cut filter having a characteristic of blocking near-infrared rays from the display screen by containing a near-infrared absorbing compound having an absorption maximum at a wavelength of about 800 to 1100 nm. To do.
When the display filter of the present invention is applied to, for example, a plasma display filter, the configuration is not particularly limited, but in general, the functional transparent layer (A), the substrate (B), and the transparent adhesive layer It is a filter consisting of (C).

The filter for plasma display comprises at least one compound A according to the present invention in at least one layer or member constituting the functional transparent layer, the substrate and the transparent adhesive layer.
The plasma display filter is provided on the plasma display screen, and generally has a functional transparent layer (A) provided on the outside air side, and a transparent adhesive layer (C) provided on the display side and adhered to the screen. A substrate (B) is provided between the functional transparent layer (A) and the transparent adhesive layer (C) (FIG. 1).

Further, for the purpose of shielding electromagnetic waves generated from the plasma display, it is preferable that the plasma display filter is further provided with a transparent conductive layer (D). In this case, the transparent conductive layer (D) is provided between the functional transparent layer (A) and the substrate (B) (FIG. 2).
The transparent conductive layer (D) may be provided between the base (B) and the transparent adhesive layer (C) (FIG. 3).
Of course, when configuring the plasma display filter, various other configurations can be made in consideration of desired required characteristics.
For example, the filter for plasma displays can be provided with a hard coat layer and a further transparent adhesive layer as desired. Moreover, it can also be set as the filter for plasma displays which provides a some functional transparent layer. These layers may also contain the compound A according to the present invention.
When the display filter of the present invention is applied to, for example, a liquid crystal display filter, the configuration is generally
(1) Filter comprising the substrate (B) (FIG. 4)
(2) Filter comprising a transparent adhesive layer (C) (FIG. 5)
(3) Filter comprising the substrate (B) and the transparent adhesive layer (C) (FIG. 6)
(4) There is a filter (FIG. 7) composed of a substrate (B) and a functional transparent layer (A).
The filter for a liquid crystal display comprises at least one compound A according to the present invention in at least one layer or member constituting the functional transparent layer, the substrate and the transparent adhesive layer.
The liquid crystal display filter is provided in an arbitrary path from the light source in the display to the outermost surface of the visual recognition unit. For example, in the case of a transmissive liquid crystal display, the liquid crystal display filter is not only on the liquid crystal display screen, but for example, a light guide plate, a backlight, a polarizing plate, a color filter, etc., with a transparent adhesive layer interposed, for example. Provided.

Hereinafter, the functional transparent layer (A) will be described.
The display filter of the present invention has an antireflection function, an antiglare function, an antireflection antiglare function, a hard coat function (friction resistance function), an antistatic function, an antistatic function, depending on the installation method for the display and the required functions. A functional transparent layer having at least one of a soiling function, a gas barrier function, and an ultraviolet ray cutting function and transmitting visible light is provided.
The functional transparent layer is a functional film itself having one or more of the above functions, or a support formed by applying a functional film to the coating method, printing method, or various conventionally known film forming methods, and further having each function. Supports can be used. The support is preferably a transparent support, and is generally a transparent glass or a transparent polymer film. In addition, as a transparent polymer film, the transparent polymer film illustrated by the base | substrate (B) mentioned later can be mentioned, for example. The thickness of the support is not particularly limited. In addition, for example, a compound A according to the present invention can be contained in a support made of a transparent polymer film. Even when the functional transparent layer is the functional film itself, the compound A according to the present invention can be contained in the film.
The functional transparent layer has either an anti-reflection (AR: anti-reflection) function for suppressing external light reflection, an anti-glare (AG: anti-glare) function, or an anti-reflection / anti-glare (ARAG) function having both functions. It is preferable to have such a function.

The functional transparent layer having the antireflection function can determine the constituent members of the antireflection film and the film thickness of each constituent member by optical design in consideration of the optical characteristics of the support that forms the antireflection film. As the functional transparent layer having an antireflection function, for example, a thin film such as fluorine-based transparent polymer resin having a refractive index of 1.5 or less in the visible light region, magnesium fluoride, silicon-based resin, silicon oxide, Single layer formed with optical wavelength of ¼ wavelength, inorganic compound thin film made of metal oxide, fluoride, silicide, boride, carbide, nitride, sulfide, etc. with different refractive index, or silicon-based Some organic compound thin films made of a resin, an acrylic resin, a fluorine-based resin, and the like are laminated in the order of a high refractive index layer and a low refractive index layer when viewed from the support. As a method for forming the inorganic compound thin film, for example, a known method such as a sputtering method, an ion plating method, a vacuum deposition method, or a wet coating method can be applied. As a method for forming the organic compound thin film, for example, a known method such as a bar coating method, a reverse coating method, a gravure coating method, a die coating method, a roll coating method, or a comma coating method can be applied. The visible light reflectance of the surface of the functional transparent layer having an antireflection function is generally adjusted to 2% or less, preferably 1.3% or less, and more preferably 0.8% or less.
The functional transparent layer having an antiglare function is generally a transparent layer with respect to a visible light region having a minute uneven surface state of about 0.1 μm to 10 μm. The functional transparent layer having an antiglare function is, for example, an acrylic resin, a silicon resin, a melamine resin, a urethane resin, an alkyd resin, a fluorine resin, or a thermosetting resin, or a photocurable resin. Inorganic particles such as silica and organic silicon compounds, or inks formed by dispersing organic compound particles such as melamine and acrylic, for example, bar coating method, reverse coating method, gravure coating method, die coating method, roll coating method It can be formed by coating and curing on a support by a method such as a comma coating method. The average particle diameter of the inorganic compound particles and the organic compound particles is generally 1 to 40 μm. The functional transparent layer having an antiglare function is, for example, a thermosetting resin such as an acrylic resin, a silicon resin, a melamine resin, a urethane resin, an alkyd resin, a fluorine resin, or a photocurable resin. Can be formed by pressing a mold having a desired haze or surface state and curing the surface to irregularities. The haze value that serves as an index of the antiglare function is generally 0.5 to 20%.
The functional transparent layer having an antireflection antiglare function can be prepared by forming an antireflection film on a film having an antiglare function or a support having an antiglare function. The visible light reflectance of the surface of the functional transparent layer having an antireflection antiglare function is generally adjusted to 1.5% or less, preferably 1.0% or less.

For the purpose of adding scratch resistance performance to the display filter of the present invention, it is preferable that the functional transparent layer has a hard coat function (friction resistance function). The functional transparent layer having a hard coat function can be prepared by forming a film having a hard coat function or a hard coat film on a support. Examples of the hard coat film include thermosetting resins such as acrylic resins, silicon resins, melamine resins, urethane resins, alkyd resins, and fluorine resins, or photocurable resins. The thickness of the hard coat film is generally about 1 to 100 μm. The hard coat film can also be used for a high refractive index layer or a low refractive index layer of a transparent functional layer having an antireflection function. Further, an antireflection film may be formed on the hard coat film, and the functional transparent layer may have both an antireflection function and a hard coat function. Similarly, the functional transparent layer may have both functions of an antiglare function and a hard coat function.
A functional transparent layer having both an antiglare function and a hard coat function can be prepared, for example, by forming an antireflection film on a hard coat film having irregularities by dispersing particles or the like. As for the surface hardness of the functional transparent layer having a hard coat function, the pencil hardness according to JISK5600 is at least H or more, preferably 2H or more.

Generally, a display filter is easily charged with static electricity, and an antistatic function may be required in consideration of prevention of dust adhesion and prevention of adverse effects on the human body. In this case, in order to provide an antistatic function, the functional transparent layer may have a certain conductivity. In general, the conductivity may be about 10 ¹¹ Ω / □ or less in terms of surface resistance. Examples of the conductive material include a known transparent conductive film such as ITO (Indium Tin Oxide), and a conductive film in which conductive ultrafine particles such as ITO ultrafine particles and tin oxide ultrafine particles are dispersed. Moreover, it is preferable that the layer which comprises the functional transparent layer which has any one or more functions of an antireflection function, an anti-glare function, an anti-glare function, and a hard-coat function has electroconductivity. It is preferable that the functional transparent film has a gas barrier function with respect to, for example, environmental substances or moisture. The required gas barrier function is generally 10 g / m ² · day or less in terms of moisture permeability. Examples of the film having a gas barrier function include silicon oxide, aluminum oxide, tin oxide, indium oxide, yttrium oxide, magnesium oxide, or a mixture thereof, or a metal oxide thin film obtained by adding other elements to these, Examples thereof include films made of various resins such as vinylidene chloride, acrylic resin, silicon resin, melamine resin, urethane resin, and fluorine resin. The thickness of the film having a gas barrier function is generally 10 to 200 nm in the case of a metal oxide thin film, and is generally 1 to 100 μm in the case of a resin. The film having a gas barrier function may have a single layer structure or a multilayer structure. Examples of the film having a gas barrier function against moisture include, for example, polyethylene, polypropylene, nylon, polyvinylidene chloride, vinylidene chloride and vinyl chloride, vinylidene chloride and acrylonitrile copolymers, and various resins such as fluorine resins. Mention may be made of membranes.

Further, the layer constituting the functional transparent layer having any one or more of the antireflection function, the antiglare function, the antireflection antiglare function, the antistatic function, and the hard coat function further serves as a gas barrier function. It can be. Furthermore, an antifouling function can be imparted to the surface of the functional transparent layer so that fingerprints and the like can be easily prevented or removed. The compound having an antifouling function is a compound having non-wetting properties with respect to water and / or fats and oils, and examples thereof include fluorine compounds and silicon compounds.
In addition, by forming, for example, an inorganic thin film single layer that absorbs ultraviolet rays, or an antireflection film composed of an inorganic thin film multilayer, or a transparent film containing an ultraviolet absorbing compound, on the functional transparent layer, Furthermore, an ultraviolet cut function can be imparted. When the functional transparent layer is the functional film itself, for example, it may be formed on the main surface of the transparent conductive layer by various film forming methods such as a coating method and a printing method. In the case where the functional transparent layer is a transparent substrate on which a functional film is formed or a transparent substrate having each function, the functional transparent layer may be formed, for example, on the main surface of the transparent conductive layer via an adhesive.
Hereinafter, the substrate (B) will be described.
The substrate functions as a filter support, and generally transparent glass or transparent polymer film is used in the visible light region. Examples of the transparent polymer film include polyethylene terephthalate, polyether sulfone, polystyrene, polyethylene naphthalate, polyarylate, polyether ether ketone, polycarbonate, polyethylene, polypropylene, nylon 6 and other celluloses, polyimide, triacetyl cellulose and the like. Resins, polyurethane resins, fluorine resins such as polytetrafluoroethylene, vinyl compounds such as polyvinyl chloride, polyacrylic acid, polyacrylic acid esters, polyacrylonitrile, addition polymers of vinyl compounds, polymethacrylic acid, polymethacrylic acid esters , Vinylidene compounds such as polyvinylidene chloride, vinyl compounds such as vinylidene fluoride / trifluoroethylene copolymer, ethylene / vinyl acetate copolymer Or copolymers of fluorine-based compound, polyether such as polyethylene oxide, epoxy resins, polyvinyl alcohol, polyvinyl butyral, but is not limited thereto. The substrate generally has a thickness of 10 to 250 μm, preferably 50 to 250 μm.

From the viewpoint of production efficiency, the substrate is preferably a flexible transparent polymer film, and the filter using the transparent polymer film directly bonded to the display surface as a substrate is made of the substrate glass of the display. When broken, there is an advantage that the glass can be prevented from scattering. In the present invention, the surface of the substrate may be subjected to etching treatment such as sputtering treatment, corona treatment, flame treatment, ultraviolet ray irradiation and electron beam irradiation, or undercoating treatment. A hard coat layer may be formed on at least one main surface of the substrate. Examples of the hard coat film that becomes the hard coat layer include thermosetting resins such as acrylic resins, silicon resins, melamine resins, urethane resins, alkyd resins, and fluorine resins, or photocurable resins. Can be mentioned. The thickness of the hard coat layer is about 1 to 100 μm. Further, the hard coat layer may contain one or more compounds A according to the present invention.
The display filter of the present invention, particularly the plasma display filter, preferably functions as an electromagnetic wave shielding body having a property of shielding electromagnetic waves from the display screen. The plasma display filter includes a functional transparent layer, a substrate, a transparent In addition to the adhesive layer, a transparent conductive layer (D) is preferably provided.

Hereinafter, the transparent conductive layer (D) will be described.
When the display filter is in the form of an electromagnetic wave shield, a transparent conductive layer is formed on one main surface of the substrate. The transparent conductive layer in the present invention is a transparent conductive layer composed of a single layer or a multilayer thin film. In addition, in the electromagnetic wave shield, electrical connection between the transparent conductive layer and the outside is necessary. For example, the functional transparent layer, the transparent adhesive layer, and the like secure the conduction portion while leaving the peripheral portion of the transparent conductive layer. It will be necessary. As a single transparent conductive layer, there are a conductive mesh such as a metal mesh and a conductive grid pattern film, and a transparent conductive thin film such as a metal thin film and an oxide semiconductor thin film. As the transparent conductive layer composed of a multilayer thin film, there is a multilayer thin film in which a metal thin film and a high refractive index transparent thin film are laminated. Multi-layer thin film composed of metal thin film and high refractive index transparent thin film prevents the reflection of metal in the specific wavelength region by the high-refractive index transparent thin film, the conductivity of silver and other metals and the near-infrared reflection characteristics due to free electrons. Since it can be performed, it has preferable characteristics with respect to conductivity, near-infrared cut function, and visible light transmittance. In order to obtain a display filter having an electromagnetic wave shielding function and a near-infrared cut function, a metal thin film having a high conductivity for electromagnetic wave absorption and a reflective interface for electromagnetic wave reflection and a high refractive index transparent thin film were laminated. A transparent conductive layer comprising a multilayer thin film is preferred. In order to have an electromagnetic wave shielding function necessary for a plasma display in addition to a high visible light transmittance and a low visible light reflectance, the transparent conductive layer generally has a surface resistance of 0.01 to 30Ω / □, more preferably It is desirable to be 0.1 to 15Ω / □, more preferably 0.1 to 5Ω / □. Also, the transparent conductive layer itself can have a near-infrared cut function, and the light transmittance minimum in the near-infrared wavelength region, for example, 800 to 1100 nm, can be 20% or less.
In the present invention, a preferred transparent conductive layer is 2 on the one main surface of the substrate, in the order of the high refractive index transparent thin film layer (Dt) and the metal thin film layer (Dm), with (Dt) / (Dm) as repeating units. The film is repeatedly laminated 4 times, and further formed thereon by laminating at least a high refractive index transparent thin film layer, and the surface resistance of the transparent conductive layer is 0.1 to 5Ω / □. The material for the metal thin film layer is preferably silver, gold, platinum, palladium, copper, indium, tin, or an alloy of silver and gold, platinum, palladium, copper, indium or tin. Although the content rate of the silver in the alloy containing silver is not specifically limited, Generally, it is 50 to less than 100 mass%. In the case of a metal thin film composed of a plurality of layers, at least one layer should be used without alloying silver, or when viewed from the substrate, only the first and / or outermost metal thin film layer is a silver alloy. It can be. The metal thin film layer is required to be in a continuous state rather than a discontinuous island structure from the viewpoint of conductivity, and the thickness is preferably 4 to 30 nm. In the case of a metal thin film composed of a plurality of layers, it is not necessary that all the layers have the same thickness, and further, all the layers may not be silver or a silver alloy having the same composition. Examples of the method for forming the metal thin film layer include known methods such as sputtering, ion plating, vacuum deposition, and plating.

  The transparent thin film forming the high refractive index transparent thin film layer is not particularly limited as long as it has transparency in the visible light region and has a function of preventing light reflection in the visible light region of the metal thin film layer. In general, a material having a refractive index with respect to visible light of 1.6 or more, preferably 1.8 or more is used. Examples of the material for forming such a transparent thin film include oxides such as indium, titanium, zirconium, bismuth, tin, zinc, antimony, tantalum, cerium, lanthanum, thorium, magnesium, and gallium, or the oxides of these oxides. A mixture, zinc sulfide, etc. can be mentioned, More preferably, they are a zinc oxide, a titanium oxide, an indium oxide, and a mixture (ITO) of an indium oxide and a tin oxide. The thickness of the high refractive index transparent thin film layer is not particularly limited, but is generally 5 to 200 nm. Examples of the method for forming the high refractive index transparent thin film layer include known methods such as sputtering, ion plating, ion beam assist, vacuum deposition, and wet coating. For the purpose of improving the environmental resistance of the transparent conductive layer, a protective layer made of an organic or inorganic material can be provided on the surface of the transparent conductive layer to such an extent that various properties such as conductivity and optical properties are not significantly impaired. In addition, in order to improve the environmental resistance of the metal thin film layer and the adhesion between the metal thin film layer and the high refractive index transparent thin film layer, conductivity, optical characteristics, etc. are provided between the metal thin film layer and the high refractive index transparent thin film layer. An inorganic layer can be provided to such an extent that these properties are not impaired. In addition, as a material which forms an inorganic substance layer, copper, nickel, chromium, gold | metal | money, platinum, zinc, zirconium, titanium, tungsten, tin, palladium etc., or the alloy which consists of 2 or more types of these materials is mentioned, for example. . The thickness of the inorganic layer is preferably about 0.2 to 2 nm. As a method for forming the transparent conductive layer, there is a method using a conductive mesh in addition to a method using a transparent conductive thin film. A single-layer metal mesh will be described as an example of the conductive mesh. As a single-layer metal mesh, for example, there is one in which a copper mesh layer is formed on a base. Generally, a single layer of metal mesh is formed by bonding a copper foil on a base and then processing it into a mesh. As the copper foil, rolled copper or electrolytic copper is used, and a porous copper foil having a pore diameter of 0.5 to 5 μm is preferable. The porosity of the copper foil is preferably 0.01 to 20%, more preferably 0.02 to 5%. The porosity is a value defined by P / R where R is the volume and P is the pore volume. The copper foil may be subjected to various surface treatments (for example, chromate treatment, roughening treatment, pickling, zinc / chromate treatment). The thickness of the copper foil is generally 3 to 30 μm. The aperture ratio of the light transmission portion of the metal mesh is generally 60 to 95%. The shape of the opening is not particularly limited, but it is preferably in the form of a regular triangle, a regular square, a regular hexagon, a circle, a rectangle, a rhombus, and the like, and is arranged in the plane. In general, it is preferable that one side or diameter of the opening of the light transmitting portion is 5 to 200 μm. Further, the width of the metal in the portion where the opening is not formed is preferably 5 to 50 μm. The substantial sheet resistance of the metal layer having the light transmitting portion is preferably 0.01 to 0.5Ω / □. In order to electrically connect the transparent conductive layer and the ground portion (ground conductor) of the display device, a conductive adhesive layer is provided.

Examples of the conductive adhesive and conductive adhesive used for the conductive adhesive layer include acrylic adhesives, silicon adhesives, urethane adhesives, polyvinyl butyral adhesives (PVB), and ethylene-vinyl acetate adhesives. There are materials in which metal particles such as carbon, Cu, Ni, Ag, and Fe are dispersed as conductive particles in a base material such as (EVA), polyvinyl ether, saturated polyester, and melamine resin. The volume resistivity of the conductive adhesive and the conductive adhesive is generally 1 × 10 ⁻⁴ to 1 × 10 ³ Ω · cm. Examples of the conductive adhesive and the conductive pressure-sensitive adhesive include a sheet form and a liquid form. As the conductive adhesive material, a sheet-like pressure sensitive adhesive material can be suitably used. After pasting the sheet-like adhesive material, or after applying the adhesive, it is laminated and pasted. The liquid conductive adhesive can be cured by treatment at room temperature or high temperature after application and bonding, or by irradiation with ultraviolet rays. Examples of the method for applying the liquid conductive adhesive include a screen printing method, a bar coating method, a reverse coating method, a gravure coating method, a die coating method, a roll coating method, and a comma coating method. The thickness of the conductive adhesive layer is set in consideration of the volume resistivity and necessary conductivity, and is generally 0.5 to 50 μm, preferably 1 to 30 μm. A double-sided adhesive type conductive tape having conductivity on both sides can also be used.

Hereinafter, the transparent adhesive layer (C) will be described.
In the present invention, the transparent adhesive layer is a layer made of any transparent adhesive material (adhesive, adhesive). The transparent adhesive layer is, for example, an acrylic adhesive, a silicon adhesive, a urethane adhesive, a polyvinyl butyral adhesive (PVB), an ethylene-vinyl acetate adhesive (EVA), a polyvinyl ether, a saturated polyester, a melamine resin. Formed from. In addition, as an adhesive material, a sheet form or a liquid form can be used. For example, when using a sheet-like pressure-sensitive adhesive material as the adhesive material, the sheet-like adhesive material is applied or an adhesive is applied, and then laminated and bonded. For example, when a liquid adhesive is used as the adhesive, it is cured and bonded by treatment at room temperature or high temperature after application and bonding, or by ultraviolet irradiation. Examples of the coating method include a screen printing method, a bar coating method, a reverse coating method, a gravure coating method, a die coating method, a roll coating method, and a comma coating method.
Although the thickness of a transparent adhesion layer is not specifically limited, Generally, it is 0.5-50 micrometers. The surface on which the transparent adhesive layer is formed and the surface to be bonded are preferably subjected to an easy adhesion treatment such as an easy adhesion coat or a corona discharge treatment in advance. Furthermore, after bonding through the transparent adhesive layer, the air mixed between the members at the time of bonding is defoamed or dissolved in the adhesive material to further improve the adhesion between the members. It is preferable to perform the treatment under pressure and heating conditions. The compound A dye according to the present invention can be contained in at least one layer of the transparent adhesive layer.
The display filter of the present invention contains at least one compound A according to the present invention.
In addition, in this specification, content includes not only those contained in each layer consisting of various members or films, or the transparent adhesive material, but also the state of being applied to the surface of each member or each layer. is there.

Examples of the method for incorporating the compound A according to the present invention into a display filter include the following methods (1) to (4).
(1) A method of adding to a transparent adhesive material and including it in a transparent adhesive layer,
(2) A method of kneading and containing the polymer resin,
(3) A method in which the compound A according to the present invention is dispersed or dissolved in an organic solvent containing a polymer resin or a resin monomer, and various members are cast on each layer, for example,
(4) There is a method in which the compound A according to the present invention is added to an organic solvent containing a binder resin, and various members are coated as paints and coated on each layer.
In the above method (1), the content of the compound A according to the present invention is not particularly limited. %. In the methods (2) and (3), the content of the compound A according to the present invention is not particularly limited, but is generally 10 ppm to 30% by mass with respect to the polymer resin or resin monomer. Preferably, it is 10 ppm to 20% by mass. In the method (4), the content of the compound A according to the present invention is not particularly limited. %. Moreover, generally binder resin density | concentration is 1-50 mass% with respect to the whole coating material.

In the display filter of the present invention, in addition to the compound A according to the present invention, one or more light absorbing compounds can be used in combination as long as the desired effects of the present invention are not impaired. Examples of such a light absorbing compound include, but are not limited to, compounds having desired absorption in the visible light region, such as anthraquinone compounds, phthalocyanine compounds, methine compounds, azomethine compounds, oxazine compounds, Examples include azo compounds, styryl compounds, coumarin compounds, porphyrin compounds, dibenzofuranone compounds, diketopyrrolopyrrole compounds, rhodamine compounds, xanthene compounds, and pyromethene compounds. When the display filter of the present invention is in the form of a near infrared cut filter, one or more near infrared absorbing compounds may be further contained.
The near-infrared absorbing compound is preferably a compound having an absorption maximum at about 800 to 1100 nm. The near-infrared absorbing compound is not particularly limited. For example, phthalocyanine compounds (for example, metal phthalocyanine complexes), naphthalocyanine compounds (for example, metal naphthalocyanine complexes), anthraquinone compounds, dithiol compounds (for example, nickel dithiol) Complex) and diimonium salt compounds. The concentration of these light-absorbing compounds and near-infrared-absorbing compounds should be set arbitrarily in consideration of the absorption wavelength and extinction coefficient of the compound, and the desired optical characteristics (for example, color purity and transmission characteristics) of the display filter. Can do.
The display filter of the present invention has, for example, excellent transmission characteristics without significantly impairing the brightness and visibility of the plasma display, and can improve the optical characteristics (for example, color purity and contrast) of the plasma display. it can. The display filter of the present invention can improve, for example, the optical characteristics (for example, color purity) of a liquid crystal display.

<Filter for glasses>
The filter for eyeglasses of the present invention contains at least one compound A according to the present invention in the base material. When it is contained in the base material referred to in the present invention, it is contained inside the base material. Of course, the state applied to the surface of a base material, the state pinched | interposed between the base materials, and the like are meant.
The substrate may be either a glass lens or a plastic lens. Since plastic is lighter than glass, is hard to break and has high safety, plastic lenses are particularly frequently used. The plastic lens base material may be either a thermoplastic resin or a thermosetting resin, and is not particularly limited. However, the plastic lens base material has a high light transmittance and can be molded, for example, a (meth) acrylic resin or a styrene resin. , Polycarbonate resin, allyl resin, allyl carbonate resin such as diethylene glycol bisallyl carbonate resin (CR-39), vinyl resin, polyester resin, polyether resin, polyurethane obtained by polymerization reaction of isocyanate compound and hydroxy compound such as diethylene glycol Resin, polythiourethane resin obtained by polymerization reaction of isocyanate compound and polythiol compound, transparent resin obtained by curing polymerizable composition containing (thio) epoxy compound having one or more disulfide bonds in the molecule, etc. It can be exemplified.
Preferably, a polycarbonate resin, a polyurethane resin, a polythiourethane resin, or a polyamide resin can be used.
Polycarbonate resin is a typical polymer that is obtained by the phosgene method in which dihydroxydiaryl compounds and phosgene are reacted as a main method, or the ester exchange method in which dihydroxydiaryl compounds are reacted with carbonic esters such as diphenyl carbonate. And polycarbonate resin produced from 2,2-bis (4-hydroxyphenyl) propane (bisphenol A).

The viscosity average molecular weight of the polycarbonate resin is usually 10,000 to 100,000, preferably 10,000 to 400,000.
A typical example of the polythiourethane resin is a polythiourethane resin produced from metaxylylene diisocyanate and pentaerythritol tetrakis (3-mercaptopropionate).
The polyamide resin is a resin having a dehydration polycondensate structure of a diamine compound containing an aromatic or aliphatic group and a dicarboxylic acid compound containing an aromatic or aliphatic group. Here, the aliphatic group also includes an alicyclic aliphatic group. The resin having the structure of the dehydration polycondensate of the diamine compounds and dicarboxylic acid compounds is not necessarily limited to those obtained from the dehydration polycondensation reaction. For example, ring opening of one or more lactam compounds It can also be obtained from polymerization or the like.

In particular, an amorphous polyamide resin is preferable from the viewpoint of transparency, and is generally referred to as transparent nylon. For example, Emamide's Grillamide TR-55, Grillamide TR-90, Grillamide TR-XE3805, or Hulus's Trogamide CX -7233 etc. can be illustrated.
These may be used alone or in combination. For example, a thermoplastic resin in which a polyamide resin is mixed with 30 to 0.5 parts by weight, preferably 20 to 1 part by weight, more preferably 15 to 2 parts by weight, with 100 parts by weight of a polycarbonate resin can be used.
The spectacle filter will be specifically described below.
The eyeglass filter of the present invention can be manufactured by a conventional method according to the material of the lens.
For example, in the case of a glass lens, it can be produced by forming a film containing the compound according to the present invention on a lens molded into a predetermined shape. The film formation can be performed by a conventional coating method. For example, as a method for coating the lens surface, a method in which the compound according to the present invention is dissolved in a binder resin and an organic solvent to form a paint can be mentioned. .
As binder resins, aliphatic ester resins, acrylic resins, melamine resins, urethane resins, aromatic ester resins, polycarbonate resins, aliphatic polyolefin resins, aromatic polyolefin resins, polyvinyl resins, polyvinyl alcohol resins, polyvinyl resins. Examples thereof include system-modified resins (PVB, EVA, etc.) or copolymer resins thereof.
Examples of the solvent include halogen-based, alcohol-based, ketone-based, ester-based, aliphatic hydrocarbon-based, aromatic hydrocarbon-based, ether-based solvents, and mixtures thereof.

The concentration of Compound A according to the present invention varies depending on the absorption coefficient, coating thickness, target absorption strength, target visible light transmittance, etc., but is usually 0.1 ppm to 30% by weight with respect to the weight of the binder resin. It is. The resin concentration is usually 1 to 50% by weight with respect to the whole paint. The coating material produced by the above method can form a film on a glass lens by a coating method such as a bar coder, a blade coater, a spin coater, a reverse coater, a die coater, or a spray. The film may be formed of a plurality of layers including an infrared absorber.
In the eyeglass filter of the present invention, in addition to the compound A according to the present invention, one or more light-absorbing compounds can be used in combination as long as the desired effects of the present invention are not impaired. The light absorbing compound is not particularly limited, and examples thereof include a compound having a desired absorption in a specific visible light region. Examples thereof include an anthraquinone compound, a phthalocyanine compound, a methine compound, an azomethine compound, and an oxazine. Examples thereof include compounds, azo compounds, styryl compounds, coumarin compounds, porphyrin compounds, tetraazaporphyrin compounds, fullerene compounds, rhodamine compounds, xanthene compounds, and pyromethene compounds. Further, in the case where the spectacles filter of the present invention is in the form of reducing the light transmittance of visible light having a short wavelength of 570 nm or less which makes it easily diffusely reflected and feels particularly dazzling, there is further one kind of light absorbing compound. It may be contained above.

The light absorbing compound is preferably a compound having an absorption maximum at about 440 to 570 nm. The light absorbing compound is not particularly limited, and examples thereof include a porphyrin compound (for example, a metal porphyrin complex) and a fullerene compound (for example, a fullerene having 70 carbon atoms). The concentration of these light absorbing compounds can be arbitrarily set in consideration of the absorption wavelength, the extinction coefficient, and the desired optical characteristics (for example, color purity and transmission characteristics) of the display filter.
In carrying out the present invention, for example, in the case of a plastic lens whose base material is a thermosetting resin, a method of polymerizing and curing a monomer that usually forms a target polymer is included. Examples include, but are not limited to, curing of diethylene glycol diallyl carbonate monomer, diallyl phthalate monomer, mixtures of isocyanate compounds and polyols and polythiols, and monomers used in the manufacture of corrective lenses such as acrylic monomers. Things. The polymerization method is not particularly limited, but usually cast polymerization is employed. In that case, the compound A according to the present invention is blended in the thermosetting resin blend, and the resin blend is supplied to a lens casting mold to perform a polymerization reaction, and is molded into a spectacle lens. A method of supplying the lens casting mold to the lens casting mold is not particularly limited. For example, a method of injecting the resin compound by passing it through a thin tube is used. The resin blend may be defoamed in advance by a method such as decompression, or cast polymerization may be performed in a state where air environmental factors are substantially eliminated.

The lens casting mold in the present invention is generally composed of two molds held by a gasket. A mold release agent may be applied to the mold in order to improve the mold releasability of the obtained lens. Further, a coating liquid for imparting hard coating performance to the lens material may be applied to the mold.
The method for adding the compound according to the present invention to the thermosetting resin composition will be specifically described below. The thermosetting resin composition used for polymerization and curing is roughly composed of a monomer mixture, a compound according to the present invention, a catalyst, and other additives.
Additives include catalysts such as dibutyltin dichloride, UV absorbers, internal mold release agents such as acidic phosphate esters, light stabilizers, antioxidants, reaction initiators such as radical initiators, chain extenders, and crosslinking Known resin modifiers for adjusting or improving the physical properties such as refractive index, Abbe number, heat resistance, specific gravity, and mechanical strength such as impact resistance, etc. Examples thereof include hydroxy compounds, thiol compounds, epoxy compounds, episulfide compounds, organic acids and anhydrides thereof, and olefin compounds including (meth) acrylate compounds.
If the component to be mixed in mixing the compound A according to the present invention is liquid at 0 ° C. or higher, the selection is not particularly limited, and it is appropriately selected in consideration of operability, safety, convenience and the like. For example, a method in which the monomer mixture is mixed with one of the monomer groups constituting the monomer mixture and then the monomer mixture is mixed, a method in which the monomer mixture and other additives are mixed, and then a catalyst is added, or the monomer mixture, catalyst, and The method of mixing with the mixture which consists of another additive is mentioned.
In mixing the compound A according to the present invention, the compound A according to the present invention is directly mixed, or the compound A according to the present invention is previously dissolved in a low-boiling organic solvent, and the organic solvent solution is mixed with the above-mentioned mixture. After mixing with the target component, the organic solvent may be removed by evaporation under conditions such as heating and / or reduced pressure. Examples of the organic solvent used in this case include hexane, heptane, acetone, methyl ethyl ketone, benzene, toluene, dichloromethane, chloroform, etc., but are chemically inert to the resin composition and have a moderately low boiling point. If it is a thing, it will not specifically limit.

Further, the resin composition may be mixed so that an amount corresponding to the concentration of the compound A according to the present invention required for the plastic lens is contained in the resin composition, or the monomer mixture or the resin composition. A master batch containing compound A according to the present invention at a concentration higher than the target concentration is prepared in any component, and the other components to be blended are added as necessary to dilute the present invention. The method etc. which contain the compound A which concerns on can also be mentioned.
Further, in dissolving the compound A according to the present invention, it can be heated within a range where there is no practical problem in terms of deterioration of the resin composition and pot life. In mixing the compound A according to the present invention, for example, usual methods such as stirring, shaking and bubbling can be mentioned. Further, it is often preferable to carry out defoaming treatment under reduced pressure, filtration treatment under pressure, reduced pressure, or the like after the dissolution of Compound A according to the present invention, if necessary.

Next, for example, in the case of a plastic lens whose base material is a thermoplastic resin, generally known methods such as a compression molding method, a transfer molding method, an injection molding method, and a compression injection molding method are employed. That is, the thermoplastic resin to be supplied is heated to a melting temperature or higher, introduced into a mold having the shape of a target plastic lens, and then cooled and solidified to obtain a plastic lens. At this time, a so-called insert method in which a plastic film having a target function such as a polarizing film is set in a mold in advance and the functional plastic film is integrated in the plastic lens molded by the above method is also the present invention. It does not exceed the range.
At that time, the compound A according to the present invention is blended in advance with the thermoplastic resin. There is no particular limitation on the blending method. For example, the compound A according to the present invention and a thermoplastic resin pellet are mechanically mixed at a temperature equal to or lower than the melting temperature of the pellet, and the compound A according to the present invention is applied to the surface of the pellet. As another method, the compound A according to the present invention and the thermoplastic resin pellet are kneaded at a temperature equal to or higher than the melting temperature of the pellet using an appropriate kneading machine, and the compound A according to the present invention is heated. It can be contained in a plastic resin pellet.
In supplying the thermoplastic resin to the molding machine, a drying process may be performed in advance under known conditions as necessary in order to reduce the amount of water contained in the thermoplastic resin.
The concentration of the compound A according to the present invention relative to the thermosetting resin is in the range of 0.0002 to 0.05% by weight, preferably 0.0002 to 0.01% by weight, more preferably 0.0004 to 0.01% by weight. The setting of the compounding amount of the compound A according to the present invention to the thermosetting resin composition for setting this concentration is experimentally based on the fact that the target concentration for the plastic lens is usually approximately the same. Can be easily determined.

The compound A according to the present invention is preferably localized in a range of 500 μm or less from the surface of at least one surface of the thermosetting or thermoplastic lens.
The method for incorporating the compound A according to the present invention into the thermoplastic resin composition will be specifically described below. The concentration of the compound A according to the present invention with respect to the thermoplastic resin is 0.0002 to 0.05% by weight, preferably 0.0002 to 0.01% by weight, more preferably 0.0004 to 0.01% by weight, The setting of the compounding amount of the compound A according to the present invention for the thermoplastic resin composition to achieve this concentration can be easily determined based on the fact that the concentration is usually approximately the same as the target concentration for the plastic lens. it can.
In addition, an amount corresponding to the concentration of the compound A according to the present invention required for the thermoplastic resin may be added to the thermoplastic resin supplied by the method described above, and the required book Compound A according to the present invention is mixed with a predetermined amount of a different blended thermoplastic resin in which the compound A exceeds the target amount, and finally the compound of the present invention having the target concentration in the plastic lens is supplied. A so-called master batch method in which A is set to be contained can also be adopted. At that time, for the purpose of dilution, the compound A-free thermoplastic resin according to the present invention may be used in combination. Alternatively, the thermoplastic resin mixed in the predetermined amount may be mixed in advance by a method such as melt kneading, and may be supplied to a molding machine after prescription such as pelletization as necessary.
In addition, in the thermosetting or thermoplastic plastic lens of the present invention, the present invention is applied to at least one component layer constituting a single layer or a multi-layer stack applied as a lens member on at least one surface of the plastic lens as necessary. The compound A which concerns on this can be made into the plastic lens which has the target wavelength-selective light absorptivity.

In forming a single layer or a multi-layer laminate on at least one surface of the thermosetting or thermoplastic plastic lens, a sheet layer can be attached, but the compound A according to the present invention is usually contained. It is formed by applying an organic resin coating agent.
Examples of the organic resin coating agent include (meth) acrylic resin, polyester resin, polyether resin, polyurethane resin, silicone resin, melamine resin, or the like. Alternatively, a copolymerized resin or the like may be used. As the resin, either a thermoplastic type or a thermosetting type is adopted depending on the purpose.
In application to the plastic lens, the resin is dissolved in a solvent-free or normally in a solvent to obtain a coating solution. Solvents include water, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, diacetone alcohol, isophorone, esters such as methyl acetate, ethyl acetate, butyl acetate, isobutyl acetate, amyl acetate, ethylene glycol monomethyl ether , Alcohols / esters such as ethylene glycol monoethyl ether and ethylene glycol monobutyl ether, alcohols such as methyl alcohol, ethyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, amyl alcohol, 2-ethylhexyl alcohol, dibutyl ether, Ethers such as tetrahydrofuran, aromatic hydrocarbons such as benzene, toluene, xylene, n-hexane, n-hept Aliphatic such as down, can alicyclic compounds, such as is illustrated, such as cyclohexane, solvent obtained by mixing two or more solvents selected from these may be used. The selection of these solvents is determined from the viewpoint according to the purpose, such as the solubility of the resin component, the degree of reactivity with the resin component, the boiling point, environmental harmony, and price.
Application of the coating solution to the plastic lens can be performed by a commonly used method such as a dipping method, a spray method, a spin coating method, a dip spin coating method, or a roll coating method. If necessary, the surface of the lens wafer to be coated can be previously subjected to plasma treatment, corona discharge treatment, ultraviolet irradiation treatment, chemical treatment with a silane coupling agent, sodium hydroxide, or the like. In the coating solution, a leveling agent such as silicone or fluorine can be used in combination as required.
When the organic resin coating agent is a thermoplastic resin, a thermoplastic resin component layer containing the compound A according to the present invention can be obtained by evaporating and drying the solvent after coating.

In the case where the organic resin coating agent is a thermosetting resin system, after application, the solvent is evaporated and dried, and then the compound A according to the present invention is contained by a curing reaction using means such as heat, ultraviolet rays, and electron beams. A thermosetting resin-based component layer can be obtained. Solvent drying conditions and curing reaction conditions can be applied simultaneously.
The thickness of the formed component layer is 0.05 to 100 μm, preferably 0.1 to 50 μm, more preferably 0.5 to 30 μm, and particularly preferably 0.5 to 10 μm. The concentration of the compound A according to the present invention contained in the component layer is 0.02 to 5% by weight, preferably 0.05 to 3% by weight.
The compound A according to the present invention may be contained only in the plastic lens, or may be contained only in the hard coat layer, primer layer, or other component layer formed on one side or both sides of the plastic lens. When there are a plurality of component layers, at least one of them may contain the compound A according to the present invention. Further, the compound A according to the present invention may be contained in both the plastic lens and the component layer.
As the primer layer, an aqueous acrylic-urethane resin or polyester-based thermoplastic elastomer that can improve the impact resistance of the plastic lens, is excellent in water resistance and light resistance, and has excellent adhesion to the hard coat layer described later. preferable.

The formation of the component layer containing the compound A according to the present invention will be described below with specific examples. In a frequently practiced form, a primer layer is formed on at least one surface of the thermosetting or thermoplastic lens, and a hard coat is applied to the surface to impart mechanical properties such as scratch resistance to the lens material surface. Is done. Furthermore, if necessary, a predetermined inorganic multilayer film is applied to the surface of the hard coat layer to impart antireflection performance. The primer layer not only contributes to the adhesion between the lens surface and the hard coat layer, but the main purpose is to reduce the impact resistance degradation of the lens itself caused by the hard coat and antireflection layer being applied through the buffering action of stress. It can be improved.
The compound A according to the present invention can be contained in the hard coat layer or primer layer to exhibit the selective light shielding properties required in the present invention. As the primer layer, a known method, for example, block type polyisocyanate and polyol are blended so that the equivalent ratio of isocyanate and hydroxyl group is about 0.8 to 1.25, diluted with a solvent, and a trace amount of tin-based catalyst and leveling are mixed. The compound A according to the present invention is added to the solution to which the agent is added at 0.5 to 2% by weight with respect to the resin component to obtain a primer solution. For example, the primer solution is used on both surfaces of a thiourethane thermosetting resin lens. After the dipping treatment, the polyurethane primer layer containing the compound A according to the present invention can be formed by evaporating and drying the solvent at about 120 to 140 ° C.
In the formation of the primer layer, a polyurethane-based primer layer not containing the compound A according to the present invention can be formed, and a hard coat layer containing the compound A according to the present invention can be formed thereon. Known hard coat agents can be used.

50-200 Angstrom average such as colloidal silicon oxide, colloidal aluminum oxide, colloidal antimony oxide, colloidal zirconium oxide, colloidal tungsten oxide, colloidal titanium oxide, colloidal zinc oxide, colloidal tin oxide, etc. Co-hydrolyzing a compound containing inorganic oxide particles having a particle diameter or a metal compound having no functional group such as an alkoxy metal compound having no functional group and a silane compound having a functional group such as an epoxy group or a methacryl group Examples thereof include a composition mainly composed of decomposed components. Examples of the silane compound having a functional group include γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyl-methyl-diethoxysilane, and γ-methacryloyloxypropyltrimethoxysilane. In addition to the components exemplified above, the hard coat agent can be used as a hard coat solution by being diluted with a solvent substantially inert with the components exemplified above as necessary.
The hard coat liquid is applied on the primer-coated surface of at least one surface of a plastic lens, and is usually cured by heating at 60 to 140 ° C., preferably 70 to 130 ° C. At that time, if necessary, a catalyst such as an inorganic acid may be contained in the hard coat solution. The curing reaction can also be performed by irradiating light such as ultraviolet rays. In that case, it is more preferable that the surface of the colloidal inorganic oxide surface is modified with a vinyl group-containing organic group such as a (meth) acryl group, or combined with a photoinitiator. The thickness of the hard coat layer after curing is 1 to 10 μm, preferably 2 to 5 μm.
In this way, for example, the compound A according to the present invention is added to the hard coat solution in advance at 0.5 to 2% by weight with respect to the resin component and dissolved, and a leveling agent is further added to prepare a dye-containing hard coat solution. The polyurethane primer layer is formed by dipping both sides of the thermosetting resin lens having the primer layer on both sides with the dye-containing hard coat solution, evaporating and drying the solvent, and then curing at 120 ° C. for 3 hours, for example. Thus, a plastic lens having a hard coat layer containing the compound A according to the present invention is obtained.
The plastic lens containing Compound A according to the present invention is subjected to functional treatments that are possible within the conventional technical range, such as multi-coating (antireflection layer), antifogging treatment, water repellent treatment, or antistatic treatment, as necessary. Also good. Further, by using a spectacle lens, a myopia lens or a presbyopia lens can be obtained. By using the spectacle lens of the present invention as a presbyopia lens, it can be suitably used as protective glasses for the elderly with weak eyes.

EXAMPLES Hereinafter, although a production example and an Example demonstrate this invention further in detail, this invention is not limited to these.
In addition, in the following production examples, examples and comparative examples, the measurement of the absorption spectrum uses a toluene solution with a concentration of 0.01 g / L, using a U-3500 type self-recording spectroscopic clock manufactured by Hitachi, Ltd. as a measuring instrument, Measurement was performed at an optical path length of 10 mm.
(Production Example 1) Production of p-tert-butylcalix [4] arene Am. Chem. Soc. , 103, 3782 (1981), and p-tert-butylcalix [4] arene was synthesized.

(Production Example 2) Production of pn-hexyl-calix [4] arene In Production Example 1, the same procedure as in Production Example 1 except that pn-hexylphenol was used instead of p-tert-butylphenol. To synthesize pn-hexylcalix [4] arene.

Example 1 Production of Compound of Example Compound No. 1-1 5.0 g of p-tert-butylcalix [4] arene synthesized in Production Example 1 was added to 60 mL of chloroform and stirred at room temperature for 10 minutes. To this mixture, 2.7 g of potassium hydroxide, 13.1 g of methyl iodide and 60 g of water were added, and the mixture was stirred at room temperature for 24 hours. The reaction product was allowed to stand to remove the aqueous layer, and then the chloroform layer was washed 3 times with 150 mL of water. Furthermore, after distilling off chloroform, 50 mL of methanol was added to the residue, and the solid matter was filtered. The filtered solid was dried and recrystallized with a mixed solution of chloroform / methanol (volume ratio: 5/3) to obtain 3.4 g of white crystals. This white crystal was a compound in which R1 is a tert-butyl group and R2 is a methyl group at the para position with respect to the phenolic hydroxyl group of the compound represented by the general formula (4).
Next, 3.0 g of the above white crystals were added to 60 mL of benzene and stirred at room temperature for 10 minutes. To this mixture, 0.21 g of metallic sodium and 60 mL of 2-propanol were added, and the mixture was further stirred at room temperature for 10 minutes. After raising the temperature of the mixture to 80 ° C., 1.2 g of neodymium trichloride was added and stirred for 2 hours. Furthermore, after distilling off the solvent from the reaction product, 60 mL of benzene was added to the residue, followed by stirring at 80 ° C. for 6 hours. Thereafter, the mixture was cooled to room temperature, allowed to stand for 24 hours, the precipitate was removed, the supernatant was recovered, and benzene was distilled off until the reaction product was about 5 mL of solution. To this residue, 5 mL of n-hexane was added, and the precipitated solid was filtered. After drying the filtered solid, 0.7 g of blue crystals were obtained. This compound showed an absorption maximum wavelength at 585 nm in toluene, and the half width was 10.

Example 2 Production of Compound of Exemplified Compound No. 1-2 In Example 1, instead of using p-tert-butylcalix [4] arene synthesized in Production Example 1, p-synthesized in Production Example 2 was used. Compound of Exemplified Compound No. 1-2 according to the procedure described in Example 1 except that 4.6 g of n-hexylcalix [4] arene and 0.9 g of neodymium trifluoride were used instead of neodymium trichloride. 1.4 g was obtained as a blue solid. This compound had an absorption maximum wavelength at 586 nm in toluene, and the half-width was 11.

Example 3 Production of Compounds of Exemplary Compound Nos. 1-4 In Example 1, 10.0 g of ethyl bromide was used instead of methyl iodide, and 0.9 g of neodymium trifluoride was used instead of neodymium trichloride. Except that was used, according to the procedure described in Example 1, 1.3 g of the compound of Exemplified Compound No. 1-4 was obtained as a blue solid. This compound showed an absorption maximum wavelength at 585 nm in toluene, and the half width was 10.

Example 4 Production of Compounds of Illustrative Compound Nos. 1-6 In Example 1, instead of using methyl iodide, 23.4 g of p-toluenesulfonic acid 2,2,2, -trifluoroethyl ester, trichloride Except for using 0.9 g of neodymium trifluoride instead of using neodymium, 1.5 g of the compound of Exemplified Compound No. 1-6 was obtained as a blue solid according to the procedure described in Example 1. This compound showed an absorption maximum wavelength at 590 nm in toluene, and the half-value width was 13.

(Example 5) Production of Compound of Exemplified Compound No. 1-15 In Example 1, instead of using p-tert-butylcalix [4] arene synthesized in Production Example 1, p- synthesized in Production Example 2 was used. Example 1 except that 4.6 g of n-hexylcalix [4] arene and 23.4 g of p-toluenesulfonic acid 2,2,2, -trifluoroethyl ester were used instead of methyl iodide. Then, 1.5 g of the compound of Exemplified Compound No. 1-15 was obtained as a blue solid. This compound showed an absorption maximum wavelength at 588 nm in toluene, and the half width was 13.

(Example 6) Production of compound of exemplified compound number 2-1 p-tert-butylcalix [4] arene synthesized in Production Example 1 (5.0 g) was added to chloroform (60 mL) and stirred at room temperature for 10 minutes. To this mixture, 2.7 g of potassium hydroxide, 10.1 g of 8- (2-bromoethoxy) quinoline and 60 g of water were added and stirred at room temperature for 24 hours. The reaction product was allowed to stand to remove the aqueous layer, and then the chloroform layer was washed 3 times with 150 mL of water. Furthermore, after distilling off chloroform, 50 mL of methanol was added to the residue, and the solid matter was filtered. The filtered solid was dried and then recrystallized with a mixed solution of chloroform / methanol (volume ratio: 5/3) to obtain 5.2 g of white crystals. This white crystal was a compound in which R1 was a tert-butyl group and R4 was a quinolinyl group substituted at the 8-position with respect to the phenolic hydroxyl group of the compound represented by the general formula (9).
Next, 1.0 g of the above white crystals was added to 20 mL of dichloromethane and stirred at room temperature for 10 minutes. To this mixture, a mixed solution of 0.48 g of neodymium (III) p-methylbenzenesulfonate and 20 mL of methanol was added, and the mixture was further stirred at room temperature for 10 minutes. To this mixture, 0.1 g of triethylamine was added and stirred for 2 hours. Further, after the solvent was distilled off from the reaction product, 5 mL of n-hexane was added to the residue, and the precipitated solid was filtered. After drying the filtered solid, 0.6 g of blue crystals were obtained. This compound had an absorption maximum wavelength at 587 nm in toluene, and the half-width was 10.

(Example 7) Manufacture of display filter A triacetyl cellulose (TAC) film (thickness: 80 μm) as a base, and the following functional transparent film as a functional transparent layer on one side thereof is rolled to It was formed continuously with a roll. That is, a photopolymerization initiator is added to a polyfunctional methacrylate resin, and a coating liquid in which ITO fine particles (average particle size: 10 nm) are further dispersed is applied with a gravure coater and UV cured to form a conductive hard coat film. (Film thickness: 3 μm) was formed. A fluorine-containing organic compound solution is coated on the microgravure coater, dried at 90 ° C and thermally cured to form an antireflective film (film thickness: 100 nm) with a refractive index of 1.4. Hard coat function (Pencil hardness: 2H), antireflection function (surface visible light reflectance: 0.9%), antistatic function (surface resistance: 7 × 10 ⁹ Ω / □), functional transparent film having antifouling function Formed.
On the other hand, the compound of Exemplified Compound No. 1-1 produced in Example 1 was dissolved in an ethyl acetate / toluene (50: 50% by mass) solvent to prepare a diluted solution.
Acrylic pressure-sensitive adhesive (80% by mass) and a dilute solution (20% by mass) containing the compound of Example Compound No. 1-1 are mixed and dried on the TAC surface of the functional transparent film / TAC film by a comma coater. The film was applied to a film thickness of 25 μm and dried to form a transparent adhesive layer. A release film was laminated on the surface of the transparent adhesive layer and wound into a roll to produce a display filter having a release film.
In addition, the dilution liquid was prepared so that the compound of exemplary compound number 1-1 might contain 1650 (mass) ppm in the dry adhesive material. Furthermore, the display filter was cut into a sheet shape, the release film was peeled off, and was bonded to the front surface of the plasma display panel (display portion 920 mm × 520 mm) using a single wafer laminator. At this time, sheet cutting and bonding position alignment were performed so that the transparent adhesive layer portion was bonded to the entire display portion. After pasting, it was autoclaved at 60 ° C. and 2 × 10 ⁵ Pa to obtain a display device equipped with a display filter.
The display filter produced above was measured and evaluated for the following items. The evaluation results are shown in Tables 1 and 2.
(I) Plasma display contrast ratio (maximum luminance / minimum luminance ratio)
The plasma display was evaluated before and after the display filter was mounted. The measurement method is the brightness of the maximum brightness (cd / m ² ) at the time of white display on the plasma display and the minimum brightness (cd / m ² ) at the time of black display when the ambient brightness is 100 lx. The contrast ratio (maximum luminance / minimum luminance ratio) was determined using a meter (LS-110). The contrast ratio before the display filter was mounted was 20.
(II) Heat resistance test of display filter The display filter was evaluated by storing at 80 ° C. and 85% RH for 100 hours. The measuring method is to measure the small pieces of the display filter before and after the heat resistance test using a spectrophotometer (U-300) manufactured by Hitachi, Ltd., and the transmittance at 595 nm is 610 nm. The ratio to the transmittance in% (%) (transmittance at 595 nm / transmittance at 610 nm × 100) was evaluated.
(III) Color purity of emission color of plasma display Evaluation was performed before and after forming a filter for display. In the three primary colors of red (R), green (G), and blue (B), RGB chromaticity (x, y) was measured using a CRT color analyzer (CA100) manufactured by Minolta. The closer the chromaticity of the three primary colors is to the chromaticity determined by the NTSC system, the better.

(Examples 8 to 12) Preparation of display filter In Example 7, instead of using the compound of Exemplified Compound No. 1-1 when forming the adhesive layer, Exemplified Compound No. 1-2 produced in Example 2 was used. Compound of Example Compound No. 1-4 (Example 9) produced in Example 3, Compound of Example Compound No. 1-4 (Example 9), Compound of Example Compound No. 1-6 produced in Example 4 (Example 10), Except that the compound of Example Compound No. 1-15 (Example 11) produced in Example 5 and the compound of Example Compound No. 2-1 (Example 12) produced in Example 6 were used, this was carried out. A display filter was produced by the method described in Example 7, and a display device equipped with the display filter was obtained.
Table 1 and Table 2 show the results of measurement and evaluation of the produced display filter in the same manner as in Example 7.

(Comparative Example 1) Production of display filter In Example 7, a display filter was produced by the method described in Example 7 except that the compound of Exemplified Compound No. 1-1 was not used when forming the adhesive layer. Furthermore, a display device equipped with the display filter was obtained.
Table 1 and Table 2 show the results of measurement and evaluation of the produced display filter in the same manner as in Example 7.

(Comparative example 2) Preparation of display filter In Example 7, when forming an adhesive layer, instead of using the compound of Exemplified Compound No. 1-1, as a comparative compound, a JP-A represented by the following formula (11) A display filter was produced by the method described in Example 7 except that the compound described in JP-A-2008-268331 was used, and a display device equipped with the display filter was obtained. Table 1 and Table 2 show the results of measurement and evaluation of the produced display filter in the same manner as in Example 7.

Table 1
(I) Plasma display contrast ratio (maximum luminance / minimum luminance ratio)
(II) Heat resistance test of display filters
Ratio (%): 595 nm transmittance / 610 nm transmittance × 100

Table 2
(III) Color purity of emission color of plasma display

From Table 1, it can be seen that the contrast of the plasma display equipped with the display filter of the present invention is greatly improved. Moreover, it turns out that the heat-and-moisture resistance of the display filter of this invention is excellent.
From Table 2, it can be seen that the contrast and color purity of the plasma display equipped with the display filter of the present invention, particularly the color purity of red, is greatly improved.

(Example 13) Production of filter for display 0.018% by mass of compound of Exemplified Compound No. 1-1 synthesized in Example 1 in polyethylene terephthalate (PET) pellets, and further for correcting the chromaticity of white light emission After mixing 0.004 mass% of red pigment PS-Red-G [manufactured by Mitsui Chemicals, Inc.], it was melted at 260 to 280 [deg.] C. to produce a PET film (thickness: 250 [mu] m) by an extruder. Thereafter, the PET film was biaxially stretched to prepare a film-like substrate (thickness: 125 μm) containing the compound of Exemplified Compound No. 1-1 and the red dye PS-Red-G in the substrate.
Furthermore, the following functional transparent film was continuously formed by roll-to-roll as a functional transparent layer on one surface of the film-like substrate wound up in a roll. That is, a photopolymerization initiator is added to a polyfunctional methacrylate resin, and a coating liquid in which organic silica fine particles (average particle size: 15 μm) are further dispersed is applied and UV-cured to produce an antiglare function (haze value: 5%) and a functional transparent film (thickness: 3 μm) having a hard coat function (pencil hardness: 2H). Then, the transparent adhesive layer was formed on the film-like base | substrate surface on the opposite side to a functional transparent film using the acrylic adhesive.
A release film was laminated on the surface of the transparent adhesive layer and wound into a roll to produce a display filter having a release film. Further, the display filter was cut into a sheet shape, the release film was peeled off, and bonded to the front surface of the plasma display panel (display portion 920 mm × 520 mm) using a single-wafer laminator. At this time, sheet cutting and bonding position alignment were performed so that the transparent adhesive layer portion was bonded to the entire display portion. After pasting, autoclaving was performed under conditions of 60 ° C. and 2 × 10 ⁵ Pa to obtain a display device equipped with a display filter. This display filter had a transmittance at 595 nm of 30% with respect to a transmittance at a wavelength of 610 nm. In addition, the plasma display equipped with this display filter improved the bright contrast ratio under the condition of ambient illuminance of 100 lx to 37, compared with 20 before the display filter was installed.

(Example 14) Manufacture of display filter A biaxially stretched polyethylene terephthalate film (PET) (thickness: 188 μm) as a base, and on one surface thereof, in order from the PET film, an ITO thin film (film thickness: 40 nm), silver Thin film (film thickness: 11 nm), ITO thin film (film thickness: 95 nm), silver thin film (film thickness: 14 nm), ITO thin film (film thickness: 90 nm), silver thin film (film thickness: 12 nm), ITO thin film (film thickness: 40 nm) in total, 7 transparent conductive layers were formed, and a transparent laminate having a transparent conductive layer having a surface resistance of 2.2 Ω / □ was produced. The compound of Exemplified Compound No. 1-4 synthesized in Example 3 and the red dye PS-Red-G (manufactured by Mitsui Chemicals) were dissolved in an ethyl acetate / toluene (50:50 mass%) solvent. Diluted solution.
Acrylic pressure-sensitive adhesive (80% by mass) and this dilute solution (20% by mass) are mixed, applied to the surface of the substrate side of the transparent laminate with a comma coater to a dry film thickness of 25 μm, dried and adhered. A release film was laminated on the surface to form a transparent adhesive layer sandwiched between the release film and the substrate of the transparent laminate. The adhesive material had a refractive index of 1.51 and an extinction coefficient of 0. In addition, the compound of exemplary compound number 1-4 and red pigment | dye PS-Red-G were prepared so that it might respectively contain 1150 (mass) ppm and 1050 (mass) ppm in the dry adhesive material.

On the other hand, a gravure coater is applied to one surface of a triacetyl cellulose film (thickness: 80 μm) by adding a photopolymerization initiator to a polyfunctional methacrylate resin and further dispersing ITO fine particles (average particle size: 10 nm). Was applied and cured with UV to form a conductive hard coat film (film thickness: 3 μm). A fluorine-containing organic compound solution is coated on the microgravure coater, dried at 90 ° C and thermally cured to form an antireflective film (film thickness: 100 nm) with a refractive index of 1.4. Hard coat function (Pencil hardness: 2H), gas barrier function (moisture permeability: 1.8 g / m ² · day), antireflection function (visible surface light reflectance: 1.0%), antistatic function (surface resistance: 7 × 10 ⁹ Ω / □), an antireflection film was produced as a functional transparent layer having an antifouling function. On the other main surface of the antireflection film, an acrylic pressure-sensitive adhesive and a diluent [ethyl acetate / toluene (50: 50% by mass)] are applied and dried to form a transparent pressure-sensitive adhesive layer having a thickness of 25 μm and further separated. A mold film was laminated. The roll-shaped transparent laminate / adhesive / release film was cut into a size of 970 mm × 570 mm and fixed on a glass support plate with the transparent conductive layer surface facing up. Furthermore, using a laminator, the antireflection film was laminated only on the inner side, leaving the conductive portion so that the peripheral portion 20 mm of the transparent conductive layer was exposed. Further, a silver paste was screen-printed in a range of a width of 22 mm at the peripheral edge so as to cover the exposed conductive portion of the transparent conductive layer, and dried to form an electrode having a thickness of 15 μm. A display filter having an electromagnetic wave shielding function having a release film on the transparent adhesive layer surface was prepared by removing from the glass support plate. Furthermore, the release film of the display filter is peeled off and bonded to the front surface of the plasma display panel (display unit 920 mm × 520 mm) using a single wafer laminator, and then at 60 ° C. and 2 × 10 ⁵ Pa. Autoclaved. The electrode part of the display filter and the ground part of the plasma display panel were connected using a conductive copper foil adhesive tape to obtain a display device equipped with the display filter.
In the plasma display equipped with this display filter, the transmittance at 595 nm was 37% with respect to the transmittance at 610 nm. Also, the plasma display equipped with the display filter improved the bright spot contrast ratio under the condition of ambient illuminance of 100 lx to 44, compared with 20 before the display filter was formed. Moreover, even when a home VTR was brought close to a plasma display as 0.5 m as an electronic device using an infrared remote controller, the VTR did not malfunction. When the display filter was not attached, the VTR malfunctioned even when the VTR was moved 5 m away from the plasma display.

Example 15 Production of Display Filter The compound of Exemplified Compound No. 1-6 synthesized in Example 4 was dissolved in an ethyl acetate / toluene (50: 50% by mass) solvent to obtain a diluted solution. An acrylic pressure-sensitive adhesive (80% by mass) and a diluent (20% by mass) containing the compound of Exemplified Compound No. 1-6 are mixed, and a dry film thickness is formed by a die coater on the surface of the polyethylene terephthalate film (75 μm). A filter for display was manufactured by coating and drying to 20 μm. In addition, the dilution liquid was prepared so that the compound of exemplary compound number 1-6 might contain 1200 (mass) ppm in the dry adhesive material. In this display filter, the transmittance at 595 nm was 19% with respect to the transmittance at a wavelength of 610 nm. When this display filter is attached to a transmissive liquid crystal display screen (with a color filter) whose red chromaticity (x, y) is (0.612, 0.335), the red chromaticity is (0 .616, 0.332). That is, when the display filter of the present invention is mounted, the red chromaticity approaches the red chromaticity (0.670, 0.330) determined by the NTSC system.

(Example 16) Manufacture of eyeglass filter In a 500 mL separable flask equipped with a thermometer, a stirrer, and a nitrogen seal tube, 200 parts of polyoxytetramethylene glycol having an average molecular weight of 1014 (manufactured by Hodogaya Chemical Co., Ltd .: PTG-1000N) The mixture was heated with stirring in a nitrogen stream and dehydrated under reduced pressure of 100 to 110 ° C./3 to 5 mmHg for 1 hour. After dehydration, 170 parts of 4,4′-methylene-bis (cyclohexyl isocyanate) (manufactured by Sumitomo Bayer Urethane: Desmodur W) was added and reacted at 120 to 130 ° C. for 2 hours to produce a prepolymer. The obtained prepolymer was a colorless transparent liquid, and had an NCO content of 9.9%, a viscosity of 8600 mPa · s / 30 ° C., and 750 mPa · s / 60 ° C.
After heating 100 parts by weight of the obtained prepolymer to 70 ° C., 0.10 parts by weight of the compound of Example Compound No. 1-1 synthesized in Example 1 was added and mixed, and then melted at 120 ° C. 4 , 4'-methylene-bis (2-chloroaniline) 31.4 parts by weight and defoamed. This mixture was poured into a mold preheated at 100 ° C. and heat-cured at 100 ° C. for 24 hours to produce a spectacle lens having a lens thickness of about 2.6 mm.
In the observation through the obtained lens, for example, the lines of the twigs of trees under clear weather and the contrast of red, yellow and green looked very clear.

(Example 17) Preparation of filter for glasses 200 parts of polyoxytetramethylene glycol having an average molecular weight of 1014 (manufactured by Hodogaya Chemical Co., Ltd .: PTG-1000N) was added to a 500 mL separable flask equipped with a thermometer, a stirrer, and a nitrogen seal tube. The mixture was heated with stirring in a nitrogen stream and dehydrated under reduced pressure of 100 to 110 ° C./3 to 5 mmHg for 1 hour. After dehydration, 131 parts of isophorone diisocyanate (Bayer's Desmodule I) was added and reacted at 120 to 130 ° C. for 2 hours to prepare a prepolymer. The obtained prepolymer was a colorless and transparent liquid, and had an NCO content of 9.7%, a viscosity of 6900 mPa · s / 30 ° C., and 900 mPa · s / 60 ° C.
After 100 parts by weight of the obtained prepolymer was heated to 70 ° C., 0.10 parts by weight of the compound of Example Compound No. 1-4 synthesized in Example 3 was added and mixed, and then melted at 120 ° C. The mixture was defoamed and mixed with 36.5 parts by weight of 4,4'methylene-bis (2,6-diethylaniline). This mixture is poured into a mold preheated at 100 ° C., and molding is quickly completed according to a pot life of several minutes, and heat curing is performed at 100 ° C. for 24 hours. Manufactured.

Subsequently, after mixing 626 parts of methanol and 221.8 parts of aqueous emulsion polyurethane (manufactured by Nikka Chemical: Neo sticker 700, solid content concentration 37%), methanol-dispersed titanium dioxide antimony pentoxide-silicon dioxide composite fine particle sol (catalyst) A primer composition was produced by mixing 309.6 parts of Kasei Kogyo Co., Ltd. (solid content concentration: 20 wt%) and 0.25 parts of a silicon surfactant (manufactured by Nippon Unicar Co., Ltd .: L-7604) and stirring well.
This primer composition was applied onto the spectacle lens by a dipping method (pickup speed: 15 cm / min). The applied spectacle lens was heat-cured at 100 ° C. for 20 minutes to form a primer layer having a film thickness of 1.0 μm and a refractive index of 1.67 on the substrate.
Further, 78 parts of methanol, 100.3 parts of butyl cellosolve, 1380.9 parts of methanol-dispersed titanium dioxide antimony pentoxide-silicon dioxide composite fine particle sol, methanol-dispersed colloidal silica (manufactured by Catalyst Kasei Kogyo Co., Ltd .: Oscar 1132 solid content concentration 30% by weight ) After 61.42 parts were mixed, 289.9 parts of γ-glycidoxypropyltrimethoxysilane were mixed. To this mixed solution, 80.1 parts of 0.05N hydrochloric acid aqueous solution was added dropwise with stirring. After further stirring for 4 hours, the mixture was aged overnight. In this solution, 4.4 parts of magnesium perchlorate, 0.6 parts of a silicon surfactant (manufactured by Nihon Unicar: L-7001) and 2.3 parts of a hindered amine light stabilizer (Sankyo LS-770) are added. The mixture was added and stirred for 4 hours, and then aged for a whole day and night to prepare a hard coat composition.
This hard coat composition was applied on the primer layer obtained by forming the primer layer by a dipping method (pickup speed 25 cm / min). The applied spectacle lens was heat-cured at 80 ° C. for 30 minutes and then heat-cured at 120 ° C. for 180 minutes. Thus, a hard coat layer having a thickness of 2.2 μm and a refractive index of 1.67 was formed on the primer layer.
In the observation through the obtained lens, for example, the lines of the twigs of trees under clear weather and the contrast of red, yellow and green looked very clear.

(Example 18) Glasses filter In a 500 mL separable flask equipped with a thermometer, a stirrer, and a nitrogen seal tube, 200 parts of 1,6-hexanediol adipate having an average molecular weight of 1007 (manufactured by Nippon Polyurethane Co., Ltd .: Nipponporan 164) was separated. The sample was taken in a bull flask, heated with stirring in a nitrogen stream, and dehydrated under reduced pressure of 100 to 110 ° C./3 to 5 mmHg for 1 hour. After dehydration, 170 parts of 4,4′-methylene-bis (cyclohexyl isocyanate) was added and reacted at 120 to 130 ° C. for 2 hours to prepare a prepolymer. The obtained prepolymer was a colorless and transparent liquid, and had an NCO content of 9.0%, a viscosity of 19000 mPa · s / 30 ° C., and 2000 mPa · s / 60 ° C.
After 100 parts by weight of the obtained prepolymer was heated to 70 ° C., 0.10 parts by weight of the compound of Example Compound No. 1-6 synthesized in Example 4 was added and mixed, and then melted at 120 ° C. The mixture was defoamed and mixed with 44.6 parts by weight of 4,4'methylene-bis (3-chloro-2,6-diethylaniline). When this mixture is poured into a mold pre-heated at 100 ° C., a polycarbonate polarizing film (Plastic plastic industry: PGC-1301) is sandwiched and cast quickly, and cured by heating at 100 ° C. for 24 hours. A lens for polarizing glasses having a thickness of about 2.2 mm was manufactured.
In the observation through the obtained lens, for example, the lines of the twigs of trees under clear weather and the contrast of red, yellow and green looked very clear.

(Example 19) Glasses filter 0.05 parts by weight of the compound of Example Compound No. 1-1 synthesized in Example 1 was mixed with 100 parts by weight of polycarbonate resin pellets (Teijin Chemicals: Panlite L-1250VX). After extruding with an extrusion extruder, a drying treatment was performed at 120 ° C. for 12 hours, and an eyeglass lens having an outer diameter of 80φ and a center thickness of 2 mm was molded using an injection molding machine adjusted to a temperature of 260 to 300 ° C.
In the observation through the obtained lens, for example, the lines of the twigs of trees under clear weather and the contrast of red, yellow and green looked very clear.

(Example 20) Glasses filter 0.05 parts by weight of the compound of Example Compound No. 2-1 synthesized in Example 6 was mixed with 100 parts by weight of polycarbonate resin pellets (Teijin Chemicals: Panlite L-1250VX). After extruding with an extrusion extruder, a drying treatment was performed at 120 ° C. for 12 hours, and an eyeglass lens having an outer diameter of 80φ and a center thickness of 2 mm was molded using an injection molding machine in which the temperature was adjusted to 260 to 300 ° C.
In the observation through the obtained lens, for example, the lines of the twigs of trees under clear weather and the contrast of red, yellow and green looked very clear.

Example 21 Glass Filter Polyamide Resin Pellets (Ms Chemie Japan: Grilamid
TR90) With respect to 100 parts by weight, 0.05 parts by weight of the compound of Exemplified Compound No. 1-4 synthesized in Example 3 was mixed and extruded with an extruder, followed by drying at 80 ° C. for 12 hours. Was molded into a spectacle lens having an outer diameter of 73φ and a center thickness of 2 mm using an injection molding machine whose temperature was adjusted to 250 to 290 ° C.
In the observation through the obtained lens, for example, the lines of the twigs of trees under clear weather and the contrast of red, yellow and green looked very clear.

According to the present invention, it is possible to provide an optical filter that is excellent in optical characteristics (for example, light absorption characteristics, narrow half-value width) and durability (for example, resistance to moist heat). More specifically, it has become possible to provide an optical filter used for a display filter such as a plasma display panel (PDP) and a liquid crystal display (LCD), and a filter for a spectacle lens.

11: Functional transparent layer (A)
12: Substrate (B)
13: Transparent adhesive layer (C)

21: Functional transparent layer (A)
22: Substrate (B)
23: Transparent adhesive layer (C)
24: Transparent conductive layer (D)

31: Functional transparent layer (A)
32: Substrate (B)
33: Transparent adhesive layer (C)
34: Transparent conductive layer (D)

42: Substrate (B)

53: Transparent adhesive layer (C)

62: Substrate (B)
63: Transparent adhesive layer (C)

71: Functional transparent layer (A)
72: Substrate (B)

Claims (5)

An optical filter comprising at least one neodymium complex of calixarene derivative. 2. The optical filter according to claim 1, wherein the neodymium complex of the calixarene derivative is at least one compound selected from the following general formula (1) and general formula (2).
[Wherein R 1 represents a linear or branched alkyl group, R 2 represents a linear or branched alkyl group or a linear or branched halogenoalkyl group, and X represents a halogen atom or a linear or branched alkoxy group. Represents)
[Wherein R3 represents a linear or branched alkyl group, R4 represents a nitrogen-containing aromatic heterocyclic group, Y represents an anion, and n represents an integer of 1 or 2]   The optical filter according to claim 2, wherein R1 in the general formula (1) or R3 in the general formula (2) is a tert-butyl group.   A display using the optical filter according to claim 1.   A spectacle lens using the optical filter according to claim 1.