TWI424202B - Optical filter - Google Patents

Description

Optical filter

The present invention relates to an optical filter using a compound having a specific structure. This optical filter is particularly useful as an optical filter for an image display device.

For compounds with a specific light absorption intensity, it can be used as CD-R (recordable compact disc), DVD-R (sequential writing method digital video disc), DVD+R (random write mode digital video disc) , a recording layer of an optical recording medium such as a blue laser recording disc, or a liquid crystal display device (LCD), a plasma display panel (PDP), an electroluminescent display (ELD, Electroluminescent. Display) Optical elements of an image display device such as a cathode ray tube display device (CRT), a fluorescent display device, or a field emission display.

Optical filter for image display devices such as liquid crystal display devices (LCDs), plasma display panels (PDPs), electroluminescent displays (ELDs), cathode ray tube display devices (CRTs), fluorescent display tubes, and electric field radiation displays In the optical device, various compounds that absorb light of a wavelength of 300 to 1100 nm are used as a light absorber.

Further, in recent years, in order to improve the image quality and color separation of the display element, the image quality has been improved, and the optical absorption agent having a wavelength of 380 to 500 nm is particularly selectively absorbed. For the light absorbing agent, the light absorption peak is particularly steep, that is, the half width of λmax is small, and the function is not lost due to light or heat.

For example, Patent Document 1 listed below discloses an organic EL display element filter which contains an ultraviolet absorber and can block light of 200 to 410 nm. However, the ultraviolet absorbing agent used in the filter for an organic EL display device has an absorption wavelength characteristic which is not necessarily suitable for the ultraviolet absorbing agent for an optical filter.

Furthermore, in the following Patent Document 2, a compound having a specific structure as a sensitizer in a photopolymerizable composition for a color filter is disclosed, and Patent Document 3 below discloses The optical information recording medium contains a compound having a specific structure, but there is no description as to the case where the compound is used as an optical filter.

[Patent Document 1] Japanese Patent Laid-Open Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei.

Accordingly, it is an object of the present invention to provide a compound which is particularly suitable for use in optical elements for optical light having a wavelength of 380 to 500 nm, particularly optical filters for image display devices.

The inventors of the present invention conducted various studies in turn and found that a compound having a specific structure has an absorption wavelength characteristic satisfying the above optical elements, and completed the present invention.

The present invention provides an optical filter which is based on the above knowledge and which is composed of at least one compound represented by the following formula (I).

(wherein R ¹ , R ² , R ³ , R ⁴ and R ⁵ each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an amine group or a hydroxyl group, and R ¹ and R ² , R ² and R ³ R ³ and R ⁴ and R ⁴ and R ⁵ each may be bonded to form a ring structure, and R ⁶ represents a cyano group, -COOR, -OCOR, -CONHR, -NHCOR, -COONHR, -NHCOOR, -COR, -SO ₂ R , -SOR, -SO ₂ NRR', a halogen atom, a nitro group or a phosphonic acid group, and R and R' each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, and a carbon number of 6 to 20. An aryl group or an aralkyl group having 7 to 20 carbon atoms, wherein the methylene group in the above alkyl group having 1 to 8 carbon atoms may be -O-, -S-, -COO-, -OCO- or -CH= CH- replaced.)

According to the present invention, there can be provided a compound which is suitable for an optical element of light having a wavelength of 380 to 500 nm and which has a narrow half width. Further, an optical filter using the compound is suitable for use in an optical filter for image display.

Hereinafter, a preferred embodiment of the optical filter of the present invention will be described in detail.

First, the compound represented by the above formula (I) will be described.

Examples of the alkyl group having 1 to 8 carbon atoms represented by R ¹ , R ² , R ³ , R ⁴ and R ⁵ in the above formula (I) and the groups R and R′ in R ⁶ include: Methyl, ethyl, propyl, isopropyl, butyl, t-butyl, tert-butyl, isobutyl, pentyl, isopentyl, tert-pentyl, hexyl, cyclohexyl, heptyl, Isoheptyl, third heptyl, n-octyl, isooctyl, trioctyl, 2-ethylhexyl, etc.; as a group of R ⁶ and R' represents a carbon number of 6 to 20 Examples of the group include a phenyl group, a naphthyl group, an inden-1-yl group, and a phenanthrene-1-yl group; and the aralkyl group having 7 to 20 carbon atoms represented by the groups R and R' in R ⁶ may, for example, be mentioned. : benzyl, phenethyl, 2-phenylpropane, diphenylmethyl, triphenylmethyl, styryl, phenylallyl, etc.; as the halogen atom represented by R ⁶ , fluorine: Chlorine, bromine, iodine.

Examples of the ring structure in which R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ and R ⁴ and R ⁵ in the above formula (I) are bonded to each other include a cyclopropane ring and a cyclobutane ring. , cyclopentane ring, cyclohexane ring, tetrahydropyran ring, piperidine ring, piperazine Ring, pyrrolidine ring, morpholine ring, thiomorpholine ring, pyridine ring, pyridyl Ring, pyrimidine ring, anthracene Ring, three a ring, a quinoline ring, an isoquinoline ring, an imidazole ring, an oxazole ring, an imidazolidinium ring, a pyrazolidine ring, an isoxazolidine ring, an isothiazolidine ring, etc., which rings may also be condensed with other rings or Replace.

^{R 1, R 2, R 3} , R 4 and R ^5, and R ^{6 is} the group R and R 'represents the number of carbon atoms of the alkyl group having 1 to 8, R ⁶ in the groups R and R' are represented by the An aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms represented by a group R and R' in R ⁶ , represented by R ¹ , R ² , R ³ , R ⁴ and R ⁵ The amine group may have a substituent. The following may be mentioned as this substituent. Further, R ¹ to R ⁶ , and R and R' are a group having a carbon atom such as an alkyl group having 1 to 8 carbon atoms, and the substituents thereof have a carbon atom-containing substituent in the following substituent. In this case, the number of carbon atoms of all of R ¹ to R ⁶ and R and R' having the substituent satisfies the predetermined range.

Examples of the substituent include a methyl group, an ethyl group, a propyl group, an isopropyl group, a cyclopropyl group, a butyl group, a second butyl group, a tert-butyl group, an isobutyl group, a pentyl group, and an isopentyl group. Third amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, dicyclohexyl, 1-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, An alkyl group such as triheptyl, n-octyl, isooctyl, trioctyl, 2-ethylhexyl, decyl, isodecyl or decyl; methoxy, ethoxy, propoxy, isopropyl Oxyl, butoxy, second butoxy, tert-butoxy, isobutoxy, pentyloxy, isopentyloxy, third pentyloxy, hexyloxy, cyclohexyloxy, heptyloxy Alkoxy groups such as benzyl, isoheptyloxy, third heptyloxy, n-octyloxy, isooctyloxy, trioctyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy; Sulfur, ethylthio, propylthio, isopropylthio, butylthio, second butylthio, tert-butylthio, isobutylthio, pentylthio, isopentylthio, third sulfol Base, hexylthio, cyclohexylthio, heptylthio, isoheptylthio, third heptanethio An alkylthio group such as n-octylthio, isooctylthio, trioctylthio, 2-ethylhexylthio; vinyl, 1-methylvinyl, 2-methylvinyl, 2-propenyl , 1-methyl-3-propenyl, 3-butenyl, 1-methyl-3-butenyl, isobutenyl, 3-pentenyl, 4-hexenyl, cyclohexenyl, dicyclohexyl Alkenyl, heptenyl, octenyl, nonenyl, pentacenyl, behenyl, thirylene, etc.; benzyl, phenethyl, diphenylmethyl, triphenyl An aralkyl group such as a styrene group or a phenylallyl group; an aryl group such as a phenyl group or a naphthyl group; an aryloxy group such as a phenoxy group or a naphthyloxy group; an arylthio group such as a phenylthio group or a naphthylthio group; Pyrimidine group Base, piperidinyl, pyranyl, pyrazolyl, tri , pyrrolyl, quinolyl, isoquinolyl, imidazolyl, benzimidazolyl, triazolyl, furyl, furanyl, benzofuranyl, thienyl, thiophene Thiophenyl, benzoquinone, thiadiazolyl, thiazolyl, benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, fluorenyl, 2-pyrrolidine Heterocyclic group such as keto-1-yl, 2-piperidone-1-yl, 2,4-dioxyimidazol-3-yl, 2,4-dioxyoxazolin-3-yl; , halogen atom such as chlorine, bromine or iodine; ethyl hydrazide, 2-chloroethyl fluorenyl group, propyl fluorenyl group, octyl decyl group, acryl fluorenyl group, methacryl fluorenyl group, phenylcarbonyl group (benzylidene group), fluorenyl group , 4-trifluoromethylbenzhydryl, trimethylethenyl, o-hydroxybenzhydryl, oxalyl, stearyl, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, positive Anthracenyl group such as octadecyloxycarbonyl or aminecarbamyl; anthracenyloxy group such as ethoxycarbonyl or benzylideneoxy; amine group, ethylamino group, dimethylamino group, diethylamino group, and butyl group Amino group, cyclopentylamino group, 2-ethylhexylamino group, Dialkylamino, anilino, chlorophenylamino, toluidine, methoxyanilino, N-methyl-anilino, diphenylamino, naphthylamino, 2-pyridylamino , methoxycarbonylamino, phenoxycarbonylamino, etidinyl, benzhydrylamino, decylamino, trimethylethylamino, dodecyl decyl, amine Mercaptoamine, N,N-dimethylaminocarbonylamino, N,N-diethylaminocarbonylamino, morpholinecarbonylamino, methoxycarbonylamino, ethoxycarbonylamino, Tributyloxycarbonylamino, n-octadecyloxycarbonylamino, N-methyl-methoxycarbonylamino, phenoxycarbonylamino, aminesulfonylamino, N,N-dimethylaminesulfonate Substituted amine group such as aminol group, methylsulfonylamino group, butylammonium group, benzoguanamine group; sulfonylamino group, sulfonyl group, carboxyl group, cyano group, sulfo group, hydroxyl group, nitro group, fluorenyl group And a trialkylalkylene group, an imido group, an amine methyl sulfonyl group, a sulfonylamino group or the like, and these groups may be further substituted. Further, the carboxyl group and the sulfo group may form a salt, a complex or a complex with an inorganic base or an organic base.

As the compound represented by the above formula (I), R ⁶ -based cyano or -COOR is preferred because it has high light resistance and can be produced at low cost. Further, the R ³ -based amine group is preferred because it has a small half width and a high solubility.

In the optical filter of the present invention, the compound represented by the above formula (I) may be used singly or in combination of plural kinds.

Specific examples of the compound represented by the above formula (I) include the following compounds No. 1 to 22.

Compound No. 11 Compound No. 12

In the optical filter of the present invention, the amount of the compound of the present invention represented by the above formula (I) is usually from 1 to 1000 mg/m ² , preferably from 1 to 1000 mg/m ² per unit area of the optical filter. It is 5~100 mg/m ² ; if the amount is less than 1 mg/m ² , the light absorption effect cannot be fully exerted, and when the amount exceeds 1000 mg/m ² , there is a filter color tone. It becomes too strong, and the display quality and the like are lowered, and further, the brightness is lowered.

Next, the optical filter of the present invention will be described.

The optical filter of the present invention contains the compound represented by the above formula (I). The compound has a maximum absorption wavelength in or near 380-500 nm and can selectively absorb and block a part of visible light or ultraviolet rays. Therefore, the optical filter of the present invention containing the compound is particularly suitable for use in the optical filter of the present invention containing the compound. An optical filter for an image display device that improves image quality. The optical filter of the present invention can be used for various applications such as analysis device applications, semiconductor device manufacturing applications, astronomical observation applications, optical communication applications, and eyeglass lenses, in addition to the use of image display devices.

The optical filter of the present invention is typically disposed in front of the display. For example, the optical filter of the present invention can be directly attached to the surface of the display, and when the front panel is disposed in front of the display, the filter can also be attached to the front side (outer side) or the back side (display side) of the front panel. .

The shape of the optical filter of the present invention is not particularly limited, and examples thereof include a primer layer, an antireflection layer, a hard coat layer, a lubricant layer, and a protective layer provided on a transparent support. . The optical filter of the present invention contains, for example, a compound of the present invention represented by the above formula (I), a light absorbing agent other than the compound of the present invention, and an optional component of various stabilizers. For example: (1) a method of including it in a transparent support or any layer; (2) a method of applying it to a transparent support or any layer; (3) including it in a transparent support and any layer A method of selecting an adhesive layer between any adjacent ones; (4) a method of separately providing a light absorbing layer containing a light absorbing agent such as a compound of the present invention in addition to any of the layers.

Examples of the material of the transparent support include inorganic materials such as glass; diethyl fluorenyl cellulose, triethyl fluorenyl cellulose (TAC), propyl fluorenyl cellulose, butyl decyl cellulose, and ethyl propyl fluorenyl. Cellulose esters such as cellulose and nitrocellulose; polydecylamine; polycarbonate; polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, polyparaphenylene Polyester such as 1,4-cyclohexanedimethylcarboxylate, polyethylene 1,2-diphenoxyethane-4,4'-dicarboxylate, butylene terephthalate; polystyrene; poly Polyolefin such as ethylene, polypropylene, polymethylpentene; acrylic resin such as polymethyl methacrylate; polycarbonate; polyfluorene; polyether oxime; polyether ketone; polyether quinone imine; A polymer material such as norbornene resin. The transmittance of the transparent support is preferably 80% or more, more preferably 86% or more. The haze value is preferably 2% or less, more preferably 1% or less. The refractive index is preferably 1.45 to 1.70. Further, in the case of the above transparent support system resin, the Tg of the resin is preferably a temperature for ensuring the temperature of the apparatus using the optical filter of the present invention (for example, a plasma display or the like), preferably 85 to 160 ° C. . If the resin Tg does not reach the guaranteed temperature, there is a case where the pigment compound in the resin interacts with the resin or other additives during use, or the resin absorbs moisture of the outside air to promote deterioration of the resin or the pigment compound. .

In the transparent support, other light absorbers other than the compound of the present invention represented by the above formula (I), an ultraviolet absorber, an antioxidant such as a phenol system or a phosphorus system, a heat stabilizer, and a flame retardant may be added. , lubricant, antistatic agent, inorganic fine particles, light resistance imparting agent, aromatic nitroso compound, ammonium compound, iminium compound, diimmonium compound, transition metal chelate, homogenizing agent, dispersing agent, interfacial activity Agents, plasticizers, etc., and various surface treatments can be applied to the above transparent support.

The light absorber other than the compound of the present invention, for example, when the optical filter is used for an image display device, may be a light absorbing agent for use in color tone adjustment, for preventing external light reflection or glare, or In the case where the image display device is a plasma display, a light absorber for preventing infrared remote control failure can be cited.

As the above-mentioned light absorbing agent for adjusting the color tone, as a method for removing orange light of 550 to 600 nm, a trimethine Indolium compound, trimethine benzoxazolium, and trimethine benzoxazolium may be mentioned. a compound, a trimethine benzothiazolium compound, a trimethyl phthalocyanine derivative, a pentamethoxazole compound, a pentamethine quinone compound, and the like, a cyanine derivative; a cyanine derivative; an azomethine pigment derivative ; xanthene pigment derivative; azo pigment derivative; Oxonol pigment derivative; benzate pigment derivative; pyrrolemethine pigment derivative; azo metal complex derivative; rose red pigment derivative; a porphyrin derivative; a dipyrromethene metal chelate compound.

As the light absorbing agent (corresponding to 480 to 500 nm) for preventing reflection or glare of external light, a trimethyl sulfonium compound, a trimethyl oxazolinium compound, a trimethyl thiazole compound, and an anthranylene group are mentioned. a trimethine cyanine derivative such as a trimethine thiazolium compound; a phthalocyanine derivative; a naphthalocyanine derivative; a porphyrin derivative; a dipyrromethene metal chelate compound.

As the above-mentioned light absorber for preventing infrared remote control failure (corresponding to 750 to 1100 nm), there may be mentioned diimine derivatives; pentamethine benzoquinone compound, pentamethazine benzoxazole compound, and pentamethazine Pentamethine cyanine derivative such as oxathiazolidine compound; heptamethine oxime compound, heptamethoxazole oxime compound, heptamethazine oxazole oxime compound, heptamethazine thiazole oxime compound, heptamethazine benzothiazole compound, etc. a cyanine derivative; a squaraine derivative; a bis(stilbene dithiol) compound, a bis(phenyldithiol) nickel compound, and a bis(camphor dithiol) nickel compound; a squaraine derivative; an azo pigment derivative; a phthalocyanine derivative; a porphyrin derivative; a dipyrromethene metal chelate compound.

In the optical filter of the present invention, the above-mentioned light absorbing agent for adjusting color tone, light absorbing agent for preventing external light reflection or glare, and light absorbing agent (near-infrared absorbing agent) for preventing infrared remote control failure, It may be contained not only in the same layer as the compound of the present invention but also in other layers. The amount of use of the optical filter is usually in the range of 1 to 1000 mg/m ² , preferably 5 to 100 mg/m ² , per unit area.

Moreover, examples of the inorganic fine particles that can be added to the transparent support include cerium oxide, titanium oxide, barium sulfate, calcium carbonate, talc, and kaolin.

Examples of the various surface treatments that can be applied to the transparent support include chemical treatment, mechanical treatment, corona discharge treatment, flame treatment, ultraviolet irradiation treatment, high frequency treatment, glow discharge treatment, active plasma treatment, and laser irradiation. Treatment, mixed acid treatment, ozone oxidation treatment, and the like.

In the case where a light absorbing layer containing a light absorbing agent is provided, the undercoat layer is a layer used between the transparent support and the light absorbing layer. The undercoat layer is formed as a layer containing a polymer having a glass transition temperature of -60 to 60 ° C, a layer having a rough surface on the side of the light absorbing layer, or a polymerization having affinity with a polymer of the light absorbing layer. The layer of matter. Moreover, the undercoat layer may be disposed on the surface of the transparent support body not provided with the light absorbing layer, and is provided for improving the adhesion of the transparent support body to the layer (for example, the anti-reflection layer, the hard coat layer) disposed thereon. It can also be provided to improve the affinity of the adhesive and the filter for bonding the filter to the image display device. The thickness of the undercoat layer is preferably 2 nm to 20 μm, more preferably 5 nm to 5 μm, more preferably 20 nm to 2 μm, more preferably 50 nm to 1 μm, and most preferably 80. Nm~300 nm. The undercoat layer containing a polymer having a glass transition temperature of -60 to 60 ° C adheres to the transparent support and the filter layer by the adhesion of the polymer. A polymer having a glass transition temperature of -60 to 60 ° C, which may be, for example, vinyl chloride, vinylidene chloride, vinyl acetate, butadiene, neoprene, styrene, chloroprene, acrylate, methacrylic acid The polymerization of an ester, acrylonitrile or methyl vinyl ether or the copolymerization of these is obtained. The glass transition temperature is preferably 50 ° C or lower, more preferably 40 ° C or lower, more preferably 30 ° C or lower, more preferably 25 ° C or lower, and most preferably 20 ° C or lower. The elastic modulus of the undercoat layer at 25 ° C is preferably from 1 to 1000 MPa, more preferably from 5 to 800 MPa, most preferably from 10 to 500 MPa. The surface of the light absorbing layer is an undercoat layer of a rough surface by adhering a transparent support to the light absorbing layer by forming a light absorbing layer on the rough surface. The surface of the light absorbing layer is an undercoat layer of a rough surface, which can be easily formed by coating a polymer latex. The average particle size of the latex is preferably 0.02 to 3 μm, more preferably 0.05 to 1 μm. Examples of the polymer having affinity with the binder polymer of the light absorbing layer include acrylic resin, cellulose derivative, gelatin, casein, starch, polyvinyl alcohol, soluble nylon, and polymer latex. Further, in the optical filter of the present invention, two or more undercoat layers may be provided. A solvent, a matting agent, a surfactant, an antistatic agent, a coating aid, a hardener, and the like which swell the transparent support may be added to the undercoat layer.

In the above antireflection layer, a low refractive index layer is necessary. The refractive index of the low refractive index layer is lower than the refractive index of the transparent support described above. The refractive index of the low refractive index layer is preferably from 1.20 to 1.55, more preferably from 1.30 to 1.50. The thickness of the low refractive index layer is preferably from 50 to 400 nm, more preferably from 50 to 200 nm. The low-refractive-index layer can be formed as a layer containing a fluoropolymer having a lower refractive index (disclosed in Japanese Patent Laid-Open No. Hei 57-34526, Japanese Patent Laid-Open No. Hei No. Hei 3-130103 Japanese Patent Laid-Open No. Hei 8-313702, Japanese Patent Application Laid-Open No. Hei No. Hei No. Hei No. Hei No. Hei. No. Hei. Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. Japanese Patent Laid-Open No. Hei 7-92306, and Japanese Laid-Open Patent Publication No. Hei 9-288201. In the layer containing the fine particles, voids may be formed in the low refractive index layer as micropores in between the microparticles or in the microparticles. The layer containing fine particles preferably has a void ratio of 3 to 50% by volume, more preferably 5 to 35% by volume.

In order to prevent reflection in a wide wavelength region, it is preferred to laminate a layer having a higher refractive index (medium-high refractive index layer) in addition to the low refractive index layer on the anti-reflection layer. The refractive index of the high refractive index layer is preferably from 1.65 to 2.40, more preferably from 1.70 to 2.20. The refractive index of the medium refractive index layer is adjusted to be the intermediate value between the refractive index of the low refractive index layer and the refractive index of the high refractive index layer. The refractive index of the medium refractive index layer is preferably from 1.50 to 1.90, more preferably from 1.55 to 1.70. in. The thickness of the high refractive index layer is preferably from 5 nm to 100 μm, more preferably from 10 nm to 10 μm, most preferably from 30 nm to 1 μm. in. The haze of the high refractive index layer is preferably 5% or less, more preferably 3% or less, and most preferably 1% or less. in. The high refractive index layer can be formed using a polymer binder having a relatively high refractive index. Examples of the polymer having a high refractive index include polystyrene, a styrene copolymer, a polycarbonate, a melamine resin, a phenol resin, an epoxy resin, and a cyclic (alicyclic or aromatic) isocyanate and a polyhydric alcohol. The polyurethane obtained by the reaction or the like. A polymer having another cyclic (aromatic, heterocyclic, or alicyclic) group or a halogen atom other than fluorine as a substituent has a high refractive index. It is also possible to use a polymer formed by a monomer polymerization reaction which introduces a double bond and makes radical hardening possible.

Further, in order to obtain a higher refractive index, inorganic fine particles may be dispersed in the above polymer binder. The refractive index of the inorganic fine particles is preferably 1.80 to 2.80. The inorganic fine particles are preferably formed of an oxide or sulfide of a metal. Examples of the oxide or sulfide of the metal include titanium oxide (for example, rutile, mixed crystal of rutile/anatase, anatase, amorphous structure), tin oxide, indium oxide, zinc oxide, and zirconium oxide. , zinc sulfide, etc. Among these, titanium oxide, tin oxide, and indium oxide are particularly preferred. The inorganic fine particles are mainly composed of an oxide or a sulfide of the metals, and may further contain other elements. The main component means a component having the largest content (% by weight) among the components constituting the particles. Examples of other elements include Ti, Zr, Sn, Sb, Cu, Fe, Mn, Pb, Cd, As, Cr, Hg, Zn, Al, Mg, Si, P, and S. An inorganic material which is dispersible in a solvent due to film formability or which is liquid in itself may be used. For example, an alkoxide of various elements, a salt of an organic acid, or a bond with a coordinating compound may be used. a compound (for example, a chelate), an active inorganic polymer, and formed. High refractive index layer.

An anti-glare function can be imparted to the surface of the anti-reflection layer (the function of scattering incident light by the surface to prevent the scenery around the film from being transferred to the surface of the film). For example, fine concavities and convexities are formed on the surface of the transparent film, and an anti-reflection layer is formed on the surface thereof, or after the anti-reflection layer is formed, an anti-reflection layer having an anti-glare function is obtained by forming irregularities on the surface by a printing roller. . The anti-reflection layer with anti-glare function usually has a fog value of 3 to 30%.

The hard coat layer has a higher hardness than the above transparent support. The hard coat layer preferably contains a crosslinked polymer. The hard coat layer can be formed using an acrylic, urethane-based, epoxy-based polymer, oligomer or monomer (for example, an ultraviolet curable resin). A hard coat layer may also be formed from a cerium oxide-based material.

The surface of the antireflection layer (low refractive index layer) may also form a lubricating layer. The lubricating layer has a function of imparting lubricity to the surface of the low refractive index layer to improve the scratch resistance. The lubricating layer can be formed using polyorganofluorene (for example, eucalyptus oil), natural wax, petroleum wax, higher fatty acid metal salt, fluorine-based lubricant or a derivative thereof. The thickness of the lubricating layer is preferably 2 to 20 nm.

When the compound of the present invention represented by the above formula (I) is contained in an optical filter, the above-mentioned "(3) is included in any of the adjacent ones selected from the transparent support and any of the layers. In the case of the method of the adhesive layer therebetween, after the compound of the present invention or the like is contained in the adhesive, the adhesive may be used to follow the transparent support and the adjacent ones of the respective layers. As the adhesive, a known transparent adhesive for laminated glass such as an anthraquinone, an urethane-based or an acrylic-based adhesive, a polyvinyl butyral adhesive or an ethylene-vinyl acetate-based adhesive can be used. Moreover, in the case of using the above-mentioned adhesive, a crosslinking agent such as a metal chelating agent, an isocyanate or an epoxy may be used as a curing agent as needed. Further, the thickness of the adhesive layer is preferably set to 2 to 400 μm.

In the case of using the above "(4) a method of separately providing a light absorbing layer containing a light absorbing agent such as a compound of the present invention", the compound of the present invention can be directly used to form a light absorbing layer, or The compound of the present invention is dispersed in a binder to form a light absorbing layer. As the binder, for example, natural polymer materials such as gelatin, casein gum, starch, cellulose derivatives, alginic acid, or polymethyl methacrylate, polyvinyl butyral, polyvinyl pyrrolidone, and polyethylene can be used. Synthetic polymer materials such as alcohol, polyvinyl chloride, styrene-butadiene copolymer, polystyrene, polycarbonate, and polyamide.

When the above-mentioned binder is used, an organic solvent may be used in combination, and the organic solvent is not particularly limited, and various known solvents can be used, and examples thereof include alcohols such as isopropyl alcohol; Ether alcohols such as Lucu, butyl 赛路苏, diethylene glycol butyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, diacetone alcohol; ethyl acetate, Esters such as butyl acetate and methoxyethyl acetate; acrylates such as ethyl acrylate and butyl acrylate; fluorinated alcohols such as 2,2,3,3-tetrafluoropropanol; hexane, benzene and toluene Hydrocarbons such as xylene; chlorinated hydrocarbons such as dichloromethane, dichloroethane and chloroform. These organic solvents may be used singly or in combination.

Further, the undercoat layer, the antireflection layer, the hard coat layer, the lubricating layer, the filter layer and the like can be formed by a usual coating method. Examples of the coating method include bar coating, dip coating, kiss coating, spray coating, and air knife coating. Curtain coating, roll coating, wire bar coating, gravure coating, blade coating, frost coating Lip coating, extrusion coating using a funnel (disclosed in the specification of U.S. Patent No. 2,681,294), and the like. It is also possible to form two or more layers by simultaneous coating. The simultaneous coating method is disclosed in U.S. Patent No. 2,761,791, U.S. Patent No. 2,941,898, U.S. Patent No. 3,508,947, U.S. Patent No. 3,526,528, and Nakasaki, "Coating Engineering", page 253 (1973) In the Asakura Bookstore release).

[Examples]

Hereinafter, the present invention will be further described in detail by way of Production Examples, Examples and Comparative Examples. However, the present invention is not limited by the following examples and the like.

Production Example 1 shows a production example of Compound No. 1. Further, the other compounds represented by the above formula (I) used in Examples 6 to 16 were synthesized in accordance with the above synthesis method.

Examples 1 to 5 show preparation examples of the optical filter of the present invention produced using the compound obtained in Production Example 1; and Examples 6 to 16 show the use of other compounds represented by the above formula (I) to produce the optical of the present invention. A production example of the filter; Comparative Example 1 shows a production example in which a comparative optical filter was produced using a comparative compound.

[Manufacturing Example 1] Synthesis of Compound No. 1

The reaction flask was purged with nitrogen to charge 328 g (1.85 mol) of diethylaminobenzaldehyde, 251 g (2.22 mol) of ethyl cyanoacetate and 500 g of ethanol, and 18.7 g was added dropwise at 50 ° C ( 0.189 mol) of triethylamine was heated at 70 ° C for 2.5 hours. After cooling to room temperature, the precipitated solid was separated by filtration. After washing with ethanol, it was dried under reduced pressure to give 467 g (yield: 93%) of an orange solid. The obtained orange solid was confirmed to be the target compound No. 1. The analysis results of the obtained orange solid are disclosed below.

(Analysis results) (1) ¹ H-NMR (DMSO solvent) (chemical shift ppm at the top of the peak; multiplicity; number of protons) (1.12; t; 6), (1.26; t; 3), (3.44; q; 4), (4.23; q; 2), (6.79; d; 2), (7.92; d; 2), (8.05; s; 1) (2) UV absorption measurement (chloroform solvent) λmax: 429.5 nm, ε : 5.50 × 10 ⁴ (3) Decomposition temperature (TG-DTA: 100 ml/min nitrogen gas flow, heating rate 10 ° C / min) 96.9 ° C: melting point, 272.5 ° C: peak tip

[Embodiment 1] Production of Optical Filter 1

The coating liquid was prepared in the following composition, and the coating liquid was applied onto a polyethylene terephthalate film having a thickness of 188 μm which was subjected to an easy adhesion treatment by a coating bar #9, and then dried at 100 ° C. After drying for 3 minutes, an optical filter having a film layer having a film thickness of 10 μm on a polyethylene terephthalate film (content of Compound No. 1 of 2.0 mg/m ² ) was obtained. The absorption spectrum of the optical filter was measured by an ultraviolet-visible near-infrared spectrophotometer V-570 manufactured by JASCO Corporation (Joint Corporation), and as a result, λmax was 430 nm and the half width was 47 nm.

(composition) Sumipex LG 2.5 g (acrylic resin adhesive manufactured by Sumitomo Chemical Co., Ltd., resin component: 40% by mass) Compound No. 1 2 mg methyl ethyl ketone 2.5 g

[Embodiment 2] Production of optical filter 2

The adhesive solution was prepared in the following composition, and the adhesive solution was applied onto a polyethylene terephthalate film having a thickness of 188 μm by a coating bar #30, and then dried at 100 ° C. After drying for 10 minutes, an optical filter having a film thickness of 10 μm on the polyethylene terephthalate film (content of Compound No. 1 of 2.0 mg/m ² ) was obtained. The optical filter was measured by an ultraviolet-visible near-infrared spectrophotometer V-570 manufactured by JASCO Corporation (Joint Corporation), and as a result, λmax was 429 nm and the half width was 48 nm.

(Composition) Compound No. 1 2.0 mg Acrylic Adhesive (DB bond 5541: manufactured by Diabond Co., Ltd.) 20 g methyl ethyl ketone 80 g

[Example 3] Production of optical filter 3

The following composition was melt-kneaded for 5 minutes at 260 ° C using a plastic mixer. After the kneading, it was extruded from a nozzle having a diameter of 6 mm, and a pigment-containing particulate matter was obtained by a water-cooling granulator. The pellet was formed into a sheet having a thickness of 0.25 mm (content of Compound No. 1 of 2.0 mg/m ² ) at 250 ° C using an electric press. The absorption spectrum of the thin plate was measured by an ultraviolet-visible near-infrared spectrophotometer V-570 manufactured by JASCO Corporation (Joint Corporation), and as a result, λmax was 429.5 m and the half width was 47.5 nm.

(composition) Iupilon S-3000 100 g (manufactured by Mitsubishi Gas Chemical Co., Ltd.: polycarbonate resin) Compound No. 1 0.01 g

[Embodiment 4] Production of Optical Filter 4

A UV varnish was prepared by the following composition, and the UV varnish was applied onto a polyethylene terephthalate film having a thickness of 188 μm after being easily adhered by a coating bar #9, and then dried at 80 ° C. 30 seconds. Thereafter, an ultraviolet filter of 100 mJ was irradiated by a high-pressure mercury lamp equipped with an infrared filter to obtain an optical filter having a filter layer having a cured film thickness of about 5 μm (Compound No. 1 content: 2.0 mg/m ² ) . The absorption spectrum of the optical filter was measured using an ultraviolet-visible near-infrared spectrophotometer V-570 manufactured by JASCO Corporation (Joint Corporation), and as a result, λmax was 429.5 nm and the half width was 47.6 nm.

(composition) Adeka Optomer KRX-571-65 100 g (UV hardening resin manufactured by Asahi Kasei Kogyo Co., Ltd., resin component: 80% by mass) Compound No.1 0.5 g methyl ethyl ketone 60 g

[Example 5] Production of Optical Filter 5

The coating liquid was prepared in the following composition, and the coating liquid was applied onto a polyethylene terephthalate film having a thickness of 188 μm after being easily adhered by a coating bar #9, and then dried at 100 ° C. After drying for 3 minutes, an optical filter having a film thickness of 10 μm on the polyethylene terephthalate film (content of Compound No. 1 of 2.0 mg/m ² ) was obtained. The optical filter was measured by an ultraviolet-visible near-infrared spectrophotometer V-570 manufactured by JASCO Corporation (Compact), and as a result, λmax was 430 nm and the half width was 47 nm.

(composition) Polyester TP-220 100 g (polyester resin manufactured by Synthetic Chemicals, Japan) Compound No. 1 1.0 g methyl ethyl ketone 60 g

[Examples 6 to 16] Production of Optical Filters 6 to 16

An optical filter was produced in the same manner as in Example 1 except that 2 mg of Compound No. 3, No. 4, No. 7 to No. 11, and Nos. 13 to 16 were used instead of 2 mg of Compound No. 1. The obtained optical filter was measured by an ultraviolet-visible near-infrared spectrophotometer V-570 manufactured by JASCO Corporation (Joint Corporation), and the results are shown in [Table 1].

[Comparative Example 1] Production of Comparative Optical Filter 1

UV-visible near-infrared spectrophotometer manufactured by JASCO Spectrophoto Co., Ltd. was used as an optical filter in the same manner as in Example 1 except that 2.4 mg of Comparative Compound No. 1 was used instead of 2 mg of Compound No. 1. The optical filter obtained was measured by V-570, and as a result, λmax was 354 nm and the half width was 92 nm.

[Chemical 4]

The optical filter of Comparative Example 1 does not have a maximum absorption wavelength at a specific wavelength (380 to 500 nm) and has a large half width, and therefore, there is a possibility of absorbing unnecessary light. It is clear from this that the optical filters of Examples 1 to 16 using the phthalocyanine compound of the present invention have a steep absorption peak (half width of 50 nm or less) at a specific wavelength (380 to 500 nm). The image display device, particularly the optical filter for a plasma display, is excellent in performance.

Claims (4)

An optical filter comprising at least one compound represented by the following formula (I), wherein the compound is used in an amount of from 1 to 1000 mg/m per unit area of the optical filter. ² , (wherein R ¹ , R ² , R ³ , R ⁴ and R ⁵ each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an amine group or a hydroxyl group, and R ¹ and R ² , R ² and R ^{3 respectively;} And R ³ and R ⁴ , and R ⁴ and R ⁵ may be bonded to each other to form a ring structure, and R ⁶ represents a cyano group, —COOR, —OCOR, —CONHR, —NHCOR, —COONHR, —NHCOOR, —COR, —SO _{2 .} R, -SOR, -SO ₂ NRR', a halogen atom, a nitro group, or a phosphonic acid group, and R and R' each independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, and a carbon number of 6~ An aryl group of 20 or an aralkyl group having 7 to 20 carbon atoms, wherein the methylene group in the alkyl group having 1 to 8 carbon atoms may be -O-, -S-, -COO-, -OCO- or - CH=CH-substitution). An optical filter according to claim 1, wherein in the above formula (I), R ⁶ is a cyano group or -COOR. An optical filter as claimed in claim 1, which is for use in an image display device. The optical filter of claim 3, wherein the image display device is a plasma display.