CN101055328B - Light filter - Google Patents

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Publication number
CN101055328B
CN101055328B CN2007100961066A CN200710096106A CN101055328B CN 101055328 B CN101055328 B CN 101055328B CN 2007100961066 A CN2007100961066 A CN 2007100961066A CN 200710096106 A CN200710096106 A CN 200710096106A CN 101055328 B CN101055328 B CN 101055328B
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Prior art keywords
compound
light filter
light
layer
expression
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CN101055328A (en
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富永信秀
富田敦郎
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Adeka Corp
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Asahi Denka Kogyo KK
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/01—Hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
    • H01J11/00—Gas-filled discharge tubes with alternating current induction of the discharge, e.g. alternating current plasma display panels [AC-PDP]; Gas-filled discharge tubes without any main electrode inside the vessel; Gas-filled discharge tubes with at least one main electrode outside the vessel
    • H01J11/10—AC-PDPs with at least one main electrode being out of contact with the plasma
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2203/00—Applications
    • C08L2203/16—Applications used for films

Abstract

The invention relates to a light absorber compound corresponding to the light component with the wavelength of 380-500nm. The invention provides an optical filter, which is formed by at least a compound described by general formula (I). In the formula, R1, R2, R3, R4 and R5 respective represents hydrogen atom, alkyl containing 1-8 carbon atoms, amido or hydroxyl group, R1. R1 and R2, R2 and R3, R3 and R4, R4 and R5 may forms ring structure by the connection. R6 represents cyano, -COOR, -OCOR, -CONHR, -NHCOR, -COONHR, -NHCOOR, -COR, -SO2R, -SOR, -SO2NRR', halogen atom, nitryl or phosphonyl. R and R' respectively represents hydrogen atom, alkyl with 1-8 carbon atoms, aryl with 6-20 carbon atoms or aralkyl with 7-20 carbon atoms. The methylene of the alkyl with 1-8 carbon atoms can be substituted by -O-,-S-, -COO-, -OCO- or -CH=CH-.

Description

Light filter
Technical field
The present invention relates to use the light filter of compound with ad hoc structure.This light filter is suitable to especially the device used for image display light filter.
Background technology
Specific light had compound that high strength absorbs usually as the optics composition of image display devices such as the recording layer of optical record mediums such as CD-R, DVD-R, DVD+R, blue laser recording disk, liquid crystal indicator (LCD), plasma scope plate (PDP), electroluminescent display (ELD), cathode tube display device (CRT), fluorescent display tube, field emission escope.
In the light filter of device used for image display such as liquid crystal indicator (LCD), plasma scope plate (PDP), electroluminescent display (ELD), cathode tube display device (CRT), fluorescent display tube, field emission escope, all cpds that can absorb the light of 300～1100nm wavelength is used as light absorber.
In addition, in recent years, for excitation or the look separation that makes display element is able to fully; Improve picture quality; Special demands can optionally absorb the light absorber of 380～500nm wavelength, as these light absorbers, require light absorption steep especially; The half value that is λ max is wide little, can not lose function because of light or heat etc. in addition.
For example, in following patent documentation 1, reported and contained ultraviolet light absorber, can block the OLED display element of 200～410nm light and use wave filter.But, the ultraviolet light absorber that this OLED display element is used as light filter with the ultraviolet light absorber that uses in the wave filter, its absorbing wavelength characteristic may not be fit to.
And; In following patent documentation 2; Disclose color filter with optical polymerism composition in as the compound with ad hoc structure of sensitizer; In following patent documentation 3, the optical information recording medium that contains the compound with ad hoc structure is disclosed, but for using this compound not have any hint as light filter.
Patent documentation 1: the spy opens the 2004-102223 communique
Patent documentation 2: the spy opens flat 9-105811 communique
Patent documentation 3: the spy opens the 2001-71639 communique
Summary of the invention
Therefore, the object of the present invention is to provide a kind of compound that is especially suitable for use as corresponding to employed light absorber in the optics composition of the light of 380～500nm wavelength, especially the device used for image display light filter.
Present inventors are through carry out multiple research repeatedly, and the result finds that the compound with ad hoc structure possesses the absorbing wavelength characteristic that can satisfy as above-mentioned optics composition, thereby has realized the present invention.
The present invention is based on above-mentioned discovery and makes, and a kind of light filter is provided, and it is through containing by at least a formation the in the compound of formula (I) expression.
Figure G200710096106620070423D000021
(in the formula, R 1, R 2, R 3, R 4And R 5Represent independently that respectively hydrogen atom, carbon number are 1～8 alkyl, amino or hydroxyl, R 1And R 2, R 2And R 3, R 3And R 4And R 4And R 5Also can be respectively through being connected to form ring structure, R 6Expression cyanic acid ,-COOR ,-OCOR ,-CONHR ,-NHCOR ,-COONHR ,-NHCOOR ,-COR ,-SO 2R ,-SOR ,-SO 2NRR ', halogen atom, nitro or phosphono; R and R ' represent independently that respectively hydrogen atom, carbon number are that 1～8 alkyl, carbon number are that 6～20 aryl or carbon number are 7～20 aralkyl, above-mentioned carbon number be in 1～8 the alkyl methylene also can by-O-,-S-,-COO-,-OCO-perhaps-CH=CH-replaces.)
According to the present invention, can provide to be suitable as corresponding to the optics composition of the light of 380～500nm wavelength and the compound of half value width.In addition, having used the light filter of this compound to be suitable as image shows and uses light filter.
Embodiment
Below, according to light filter of the present invention preferred embodiment at length is described.
At first, the compound by above-mentioned general formula (I) expression is described.
As in the above-mentioned general formula (I) by R 1, R 2, R 3, R 4And R 5, and R 6In the carbon number of radicals R and R ' expression be 1～8 alkyl; Can enumerate out methyl, ethyl, propyl group, isopropyl, butyl, sec-butyl, the tert-butyl group, isobutyl, amyl group, isopentyl, tertiary pentyl, hexyl, cyclohexyl, heptyl, different heptyl, uncle's heptyl, n-octyl, iso-octyl, uncle's octyl group, 2-ethylhexyl etc., as by R 6In the carbon number of radicals R and R ' expression be 6～20 aryl, can enumerate out phenyl, naphthyl, anthracene-1-base, phenanthrene-1-base etc., as by R 6In the carbon number of radicals R and R ' expression be 7～20 aralkyl, can enumerate out benzyl, phenethyl, 2-phenyl-propane, diphenyl methyl, trityl group, styryl, cinnamoyl etc., as by R 6The halogen atom of expression can be enumerated out fluorine, chlorine, bromine, iodine.
As R in the above-mentioned general formula (I) 1And R 2, R 2And R 3, R 3And R 4And R 4And R 5Respectively through connecting the ring structure that forms; Can enumerate out cyclopropane ring, cyclo-butane ring, cyclopentane ring, cyclohexane ring, amylene oxide ring, piperidine ring, piperazine ring, pyrrolidine ring, morpholine ring, thiomorpholine ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, quinoline ring, isoquinoline ring, imidazole ring 、 oxazole ring, imidazolidine ring, pyrazolidine ring 、 isoxazole alkyl ring, isothiazolidine ring etc.; These rings can condense with other ring, also can be substituted.
As by R 1, R 2, R 3, R 4And R 5, and R 6In the carbon number of radicals R and R ' expression be 1～8 alkyl, by R 6In the carbon number of radicals R and R ' expression be 6～20 aryl, by R 6In the carbon number of radicals R and R ' expression be 7～20 aralkyl, by R 1, R 2, R 3, R 4And R 5The amino of expression can have substituting group.As this substituting group, can enumerate out following group.And, R 1～R 6And R and R ' comprised that above-mentioned carbon number is the group of the carbon atom of alkyl of 1～8 etc., and, even in following substituting group, when these groups have the substituting group that contains carbon atom, include this substituent R 1～R 6And whole carbon numbers of R and R ' also are set to the scope that satisfies regulation.
As above-mentioned substituting group, can enumerate out for example alkyl such as methyl, ethyl, propyl group, isopropyl, cyclopropyl, butyl, sec-butyl, the tert-butyl group, isobutyl, amyl group, isopentyl, tertiary pentyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, dicyclohexyl, 1-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, different heptyl, uncle's heptyl, n-octyl, iso-octyl, uncle's octyl group, 2-ethylhexyl, nonyl, different nonyl, decyl; Methoxyl, ethoxy, propoxyl group, isopropoxy, butoxy, sec-butoxy, tert-butoxy, isobutoxy, amoxy, isoamoxy, uncle's amoxy, own oxygen base, cyclohexyloxy, heptan oxygen base, different heptan oxygen base, uncle's oxygen in heptan base, n-octyloxy, different octyloxy, uncle's octyloxy, 2-ethyl hexyl oxy, the ninth of the ten Heavenly Stems oxygen base, the last of the ten Heavenly stems alkoxy such as oxygen base; Methyl mercapto, ethylmercapto group, rosickyite base, different rosickyite base, butylthio, secondary butylthio, uncle's butylthio, isobutyl sulfenyl, penta sulfenyl, isoamyl sulfenyl, uncle's penta sulfenyl, own sulfenyl, hexamethylene sulfenyl, heptan sulfenyl, different heptan alkylthio group such as sulfenyl, uncle's sulfenyl in heptan, positive hot sulfenyl, different hot sulfenyl, the hot sulfenyl of uncle, the own sulfenyl of 2-ethyl; Alkenyls such as vinyl, 1-methyl ethylene, 2-methyl ethylene, 2-propenyl, 1-methyl-3-propenyl, 3-butenyl group, 1-methyl-3-butenyl group, isobutenyl, 3-pentenyl, 4-hexenyl, cyclohexenyl group, two cyclohexenyl groups, heptenyl, octenyl, decene base, 15 carbene bases, eicosylene base, melene base; Aralkyl such as benzyl, phenethyl, diphenyl methyl, trityl group, styryl, cinnamoyl; Aryl such as phenyl, naphthyl; Aryloxy group such as phenoxy group, naphthoxy; Arylthios such as thiophenyl, naphthalene sulfenyl; Pyridine radicals, pyrimidine radicals, pyridazinyl, piperazinyl, pyranose, pyrazolinyl, triazinyl, pyrrole radicals, quinolyl, isoquinolyl, imidazolinyl, benzimidazoline base, triazoline base, furyl (furyl), furyl (furanyl), benzofuranyl, thienyl, thio-phenyl, benzo thio-phenyl, Thiadiazoline base, thiazolinyl, benzothiazole quinoline base, oxazolinyl, benzoxazole quinoline base, isothiazoline base, isoxazoline-3-yl, indyl, 2-pyrrolidine-1-base, 2-piperidones-1-base, 2; 4-dioxo alkyl imidazole-3-base, 2,4-Er Yang Dai oxazolidine-heterocyclic radicals such as 3-base; Halogen atoms such as fluorine, chlorine, bromine, iodine; Acyl groups such as acetyl group, 2-chloracetyl, propiono, caprylyl, acryloyl group, methacryl, phenylcarbonyl group (benzoyl), phthalyl, 4-trifluoromethyl benzoyl, pivaloyl group, salicyl, oxalyl group, stearyl, methoxycarbonyl, ethoxy carbonyl, tert-butoxycarbonyl, n-octadecane oxygen base carbonyl, carbamyl; Acyloxy such as acetoxyl group, benzoyloxy; Amino, ethylamino, dimethylamino, diethylamino, butyl are amino, cyclopentyl is amino, the 2-ethylhexyl is amino, dodecyl is amino, anilino-, chlorophenyl amino, toluene amido, anisidino, N-methyl-anilino-, diphenyl amino, naphthyl amino, 2-pyridinylamino, methoxycarbonyl amino, phenyloxycarbonyl are amino, acetyl-amino, benzoyl-amido, formoxyl amino, pivaloyl group is amino, lauroyl is amino, carbamyl is amino, N; N-dimethylamino carbonylamino, N; N-diethylamino carbonylamino, morpholino carbonyl are amino, methoxycarbonyl is amino, ethoxy carbonyl is amino, tert-butoxycarbonyl is amino, n-octadecane oxygen base carbonylamino, N-methyl-methoxycarbonyl is amino, phenyloxycarbonyl is amino, sulfamoyl is amino, N, substituted-aminos such as N-dimethylamino sulfuryl amino, methyl sulphonyl amino, butyl sulfuryl amino, phenyl sulfonyl amino; Sulfoamido, sulfonyl, carboxyl, cyanic acid, sulfo group, hydroxyl, nitro, sulfydryl, trialkylsilkl, imide, carbamyl, sulfoamido etc., these groups also can further be substituted.In addition, carboxyl and sulfo group also can form salt, complex compound or compound with inorganic alkali or organic alkali.
As the compound by above-mentioned general formula (I) expression, R 6For cyanic acid perhaps-compound of COOR is because photostability is high, can prepare at an easy rate, so preferred.In addition, R 3For the compound of amino is wide little owing to half value, dissolubility is high, so preferred.
In the light filter of the present invention, the compound of being represented by above-mentioned general formula (I) can use separately or multiple combination use.
As the object lesson of the compound of representing by above-mentioned general formula (I), can enumerate out following compound N o.1～22.
Figure G200710096106620070423D000061
In light filter of the present invention,, be generally 1～1000mg/m by the use amount of the compound of the present invention of above-mentioned general formula (I) expression with respect to the light filter of per unit area 2, be preferably 5～100mg/m 2, when use amount is lower than 1mg/m 2The time, can not bring into play optical absorption fully, and surpass 1000mg/m 2During use, tone that might light filter became strong and reduced display quality etc., in addition, also might brightness descend.
Below, light filter of the present invention is described.
Light filter of the present invention contains the compound by above-mentioned general formula (I) expression.This compound has maximum absorption wavelength in 380～500nm scope or near it; Optionally absorption portion luminous ray or ultraviolet ray and block is particularly suitable for the device used for image display light filter that uses in the high quality as display image so contain the light filter of the present invention of this compound.Light filter of the present invention also can be used for various uses such as analytical equipment purposes, semiconductor device manufacturing purposes, astronomical sight purposes, optical communication purposes, eyeglass lens except being used for image display device.
Light filter of the present invention is arranged on the front surface of display usually.For example, can light filter of the present invention directly be attached on the surface of display, when the place ahead of display is provided with front panel, the face side of plate (outside) or inboard (display side) applying light filter in front.
About the shape of light filter of the present invention, not special restriction can be enumerated out the structure that each layers such as undercoat, anti-reflection layer, hard conating, lubricating layer, protective seam are set as required usually on transparent supporting body.As making light filter of the present invention contain the method by the optional member of the compound of the present invention of above-mentioned general formula (I) expression or the light absorber of the dye compound except compound of the present invention, various stabilizing agents, for example can enumerate out: (1) is being selected from the be arranged method of light absorbing zone of light absorbers such as containing compound of the present invention etc. of the method, (4) and any each layer branch that contain in any adjacent adhesive phase between the two in transparent supporting body and each layer arbitrarily in transparent supporting body or the method, (3) that apply on each layer arbitrarily in transparent supporting body or the method that contains in each layer arbitrarily, (2).
As the material of above-mentioned transparent supporting body, can enumerate out for example inorganic material such as glass; Cellulose esters such as diacetyl cellulose, tri acetyl cellulose (TAC), propiono cellulose, bytyry cellulose, acetyl group propiono cellulose, NC Nitroncellulose; Polyamide; Polycarbonate; Polyethylene terephthalate, PEN, polybutylene terephthalate, poly terephthalic acid-1; 4-cyclohexanedimethyleterephthalate ester, gather-1; 2-biphenoxyl ethane-4, polyester such as 4 '-dicarboxylic acid glycol ester, polybutylene terephthalate; Polystyrene; Polyolefin such as tygon, polypropylene, polymethylpentene; Acrylic resins such as polymethylmethacrylate; Polycarbonate; Polysulfones; Polyethersulfone; Polyetherketone; Polyetherimide; Macromolecular material such as polyoxyethylene, norbornene resin.The transmitance of transparent supporting body is preferably more than 80%, more preferably more than 86%.Turbidity is preferably below 2%, more preferably below 1%.Refractive index is preferably 1.45～1.70.In addition, when above-mentioned transparent supporting body was resin, the Tg of this resin preferably used the assurance serviceability temperature of the device (for example plasma scope etc.) of light filter of the present invention, is preferably 85～160 ℃.When the Tg of resin is lower than when guaranteeing serviceability temperature, the dye compound during use in the resin can with resin or other interactions such as adjuvant, or resin absorbs the moisture in the outside atmosphere and promotes resin or dye compound deterioration.
In the above-mentioned transparent supporting body; Can add except by other light absorber, ultraviolet light absorber, phenol, anti-oxidant, thermal stabilizer, fire retardant, lubricant, antistatic agent, inorganic particles, photostability imparting agent, aromatic series nitroso compound, amine salt compound, inferior amine salt compound, diimine salt compound, transition metal chelate compound, levelling agent, spreading agent, surfactant, the plastifier etc. such as Phosphorus the compound of the present invention of above-mentioned general formula (I) expression; In addition, also can carry out various surface treatments to above-mentioned transparent supporting body.
As the light absorber except the compound of the invention described above; For example; When light filter being used for the device used for image display way, can enumerating the whole usefulness of outstanding key, prevent external light reflection or mirror the light absorber of usefulness, perhaps; When image display device is plasma scope, can enumerate out the light absorber that prevents that the infrared remote control maloperation from using.
Above-mentioned light absorber as above-mentioned tone adjustment usefulness; The light absorber that uses as being used to remove 550～600nm orange-colored light can be enumerated out front three alkynes cyanine derivants such as front three alkynes benzazolyl compounds, front three alkynes benzoazole compounds, front three alkynes benzothiazole compound; Pentamethine cyanine derivants such as five Jia Que oxazole compounds, five first alkynes thiazolium compoundss; The anthocyanidin derivant; The azomethine pigment derivative; The xanthenes pigment derivative; The azopigment derivant; The oxonols pigment derivative; The benzal pigment derivative; The methylene pyrrole pigment derivative; The azo metal complex derivant; The rhodamine pigment derivative; Phthalocyanine derivates; Derivatives of porphyrin; Dipyrromethene metal chelate compounds compound etc.
Light absorber as preventing said external light reflection or mirroring usefulness (corresponding to 480～500nm), can be enumerated out front three alkynes cyanine derivants such as front three alkynes benzazolyl compounds, front three Que oxazole compound, front three alkynes thiazolium compounds, indyl (indolydene) front three alkynes thiazolium compounds; Phthalocyanine derivates; Naphthalene cyanines derivant; Derivatives of porphyrin; Dipyrromethene metal chelate compounds compound etc.
(, can enumerate out the diimine salt derivative as the above-mentioned light absorber that prevents that the infrared remote control maloperation from using corresponding to 750～1100nm); Pentamethine cyanine derivants such as five first alkynes benzindole compounds, five first alkynes benzoazole compounds, five first alkynes benzothiazole compounds; Seven first alkynes cyanine derivants such as seven first alkynes benzazolyl compounds, seven Jia Que oxazole compounds, seven first alkynes benzoazole compounds, seven first alkynes thiazolium compoundss, seven first alkynes benzothiazole compounds; Squaric acid inner salt pigment derivative; Nickel complexes such as two (talan two mercaptide) compound, two (dimercaptobenzene) nickel compound, two (camphor two mercaptan) nickel compound; Squaric acid inner salt pigment derivative; The azopigment derivant; Phthalocyanine derivates; Derivatives of porphyrin; Dipyrromethene metal chelate compounds compound etc.
In light filter of the present invention; The light absorber of above-mentioned tone adjustment usefulness, prevent external light reflection and mirror the light absorber of usefulness and prevent that the light absorber (near infrared ray absorption) that the infrared remote control maloperation is used can be contained in in one deck with compound of the present invention, also can be contained in the different layers.Usually in the per unit area light filter, their use amount is respectively 1～1000mg/m 2Scope, be preferably 5～100mg/m 2
In addition, as the above-mentioned inorganic particles that can join in the transparent supporting body, can enumerate out for example silicon dioxide, titania, barium sulphate, lime carbonate, talcum, porcelain earth etc.
As the above-mentioned various surface treatments that can on transparent supporting body, carry out, can enumerate out for example chemical treatment, mechanical treatment, Corona discharge Treatment, flame treatment, ultraviolet treatment with irradiation, high frequency processing, arc discharge processing, reactive plasma treatment, laser treatment, nitration mixture processing, ozone Oxidation Treatment etc.
When be provided with each layer arbitrarily separate contain the filter layer of light absorber the time, above-mentioned undercoat be between transparent supporting body and optical filter layer, use layer.Above-mentioned undercoat form contain the vitrifacation transition temperature for the surface of the layer of-60～60 ℃ polymkeric substance, filter layer side be the layer of uneven surface, perhaps contain polymkeric substance with filter layer have compatibility polymkeric substance layer.In addition; On the face of the transparent supporting body that filter layer is not set, undercoat is set; Can be for improve transparent supporting body with its go up to be provided with layer (for example; Anti-reflection layer, hard conating) between bounding force be provided with, also can be provided with in order to improve the bonding agent that is used for bonding light filter and image display device and the compatibility between the light filter.The thickness of undercoat is preferably 2nm～20 μ m, and more preferably 5nm～5 μ m further are preferably 20nm～2 μ m, and more preferably 50nm～1 μ m most preferably is 80nm～300nm.It is bonding with transparent supporting body and filter layer through the stickability of polymkeric substance for the undercoat of-60～60 ℃ polymkeric substance to contain the vitrifacation transition temperature.The vitrifacation transition temperature can obtain through the polymerization of for example vinyl chloride, vinylidene chloride, vinyl acetate, butadiene, neoprene, styrene, chlorbutadiene, acrylic ester, methacrylate, vinyl cyanide or methyl vinyl ether or their copolymerization for-60～60 ℃ polymkeric substance.The vitrifacation transition temperature is preferably below 50 ℃, more preferably below 40 ℃, further is preferably below 30 ℃, more preferably below 25 ℃, most preferably is below 20 ℃.The elastic modulus of undercoat under 25 ℃ is preferably 1～1000MPa, and more preferably 5～800MPa most preferably is 10～500MPa.The surface of filter layer side be the undercoat of uneven surface through on uneven surface, forming filter layer, thereby transparent supporting body and filter layer is bonding.The surface of filter layer side is that the undercoat of uneven surface can form through coat polymers latex at an easy rate.The mean grain size of latex is preferably 0.02～3 μ m, more preferably 0.05～1 μ m.As the polymkeric substance that the binder polymer with filter layer has compatibility, can enumerate out acryl resin, cellulose derivative, alginic acid, gelatin, casein, starch, polyvinyl alcohol (PVA), polyvinyl butyral, polyvinyl pyrrolidone, soluble nylon and polymer latex etc.In addition, in light filter of the present invention, two-layer above undercoat can be set also.In undercoat, also can add the solvent that makes the transparent supporting body swelling, matting agent, surfactant, antistatic agent, coating auxiliary agent, hard coat agent etc.
In the above-mentioned anti-reflection layer, low-index layer must be arranged.The refractive index of the above-mentioned transparent supporting body of refractive index ratio of low-index layer is also low.The refractive index of low-index layer is preferably 1.20～1.55, and more preferably 1.30～1.50.The thickness of low-index layer is preferably 50～400nm, is preferably 50～200nm.Low-index layer can form the layer of being made up of the low fluoropolymer of refractive index, and (spy opens clear 57-34526 number; Te Kaiping 3-130103 number; Te Kaiping 6-115023 number; Te Kaiping 8-313702 number; Te Kaiping 7-168004 number each communique record); (spy opens flat 5-208811 number with layer that sol-gal process obtains; Te Kaiping 6-299091 number; Te Kaiping 7-168003 number each communique record); Layer (the spy public clear 60-59250 number of perhaps containing particulate; Te Kaiping 5-13021 number; Te Kaiping 6-56478 number; Te Kaiping 7-92306 number; Te Kaiping 9-288201 number each communique record).Contain particulate the layer in, as between particulate or particulate in micropore, can in low-index layer, form the space.The layer that contains particulate preferably has the voidage of 3～50 volume %, more preferably has the voidage of 5～35 volume %.
In order to prevent the reflection of wide wavelength region may, in the above-mentioned anti-reflection layer, except low-index layer, the layer that also preferred range upon range of refractive index is high (in/high refractive index layer).The refractive index of high refractive index layer is preferably 1.65～2.40, and more preferably 1.70～2.20.The refractive index of middle index layer is adjusted according to the mode of the intermediate value of the refractive index of refractive index that becomes low-index layer and high refractive index layer.In the refractive index of index layer be preferably 1.50～1.90, more preferably 1.55～1.70.In/thickness of high refractive index layer is preferably 5nm～100 μ m, and more preferably 10nm～10 μ m most preferably are 30nm～1 μ m.In/turbidity of high refractive index layer is preferably below 5%, more preferably below 3%, most preferably is below 1%.In/high refractive index layer can use to have than the polymer adhesive of high index and form.As the high polymkeric substance of refractive index, can enumerate out polyurethane that polystyrene, styrol copolymer, SB, PVC, polycarbonate, polyamide, melamine resin, phenolics, epoxy resin, ring-type (ester ring type or aromatic series) isocyanates and polyol reaction obtain etc.The halogen atom that have the polymkeric substance of other ring-type (aromatic series, hetero ring type, ester ring type) base, maybe will have beyond the defluorination is also high as the refractive index of substituent polymkeric substance.Also can use through introducing the polymkeric substance that two keys form the polyreaction of radical-cured monomer.
In order to obtain higher refractive index, also can in above-mentioned polymer adhesive, disperse inorganic particles.The refractive index of inorganic particles is preferably 1.80～2.80.Inorganic particles is preferably formed by the oxide or the sulfide of metal.As the oxide or the sulfide of metal, can enumerate out titanium dioxide (for example, the mixed crystal of rutile, rutile/anatase, anatase, impalpable structure), tin oxide, indium oxide, zinc paste, zirconia, zinc sulphide etc.Wherein, preferred especially titanium dioxide, tin oxide and indium oxide.Inorganic particles is a major component with the oxide or the sulfide of these metals, can also contain other element.Said major component refers to the maximum composition of content in the composition of constituent particle (quality %).As other element, can enumerate out Ti, Zr, Sn, Sb, Cu, Fe, Mn, Pb, Cd, As, Cr, Hg, Zn, Al, Mg, Si, P, S etc.Use can according to overlay film formation property be scattered in solvent or itself be aqueous inorganic material; For example the alkoxide of various elements, organic acid salt, with coordination compound (for example chelate compound), the active inorganic polymer of coordination property compound bonding, in also can forming/high refractive index layer.
On the surface of above-mentioned anti-reflection layer, can give anti-dazzle function (make incident light produce scattering, thereby prevent that the scenery around the film from moving on to the function on film surface) on the surface.For example, can form through surface at transparent membrane trickle concavo-convex and form anti-reflection layer on its surface, perhaps form anti-reflection layer after, form on the surface with knurling rolls concavo-convex, the anti-reflection layer of acquisition with anti-dazzle function thus.Anti-reflection layer with anti-dazzle function has 3～30% turbidity usually.
Above-mentioned hard conating has the height also higher than the hardness of above-mentioned transparent supporting body.Hard conating preferably contains crosslinked polymkeric substance.Hard conating can use polymkeric substance, oligomer or the monomer formation such as (for example ultraviolet curing resins) of acrylic compounds, urethanes, epoxies.Also can form hard conating by the silica type material.
The surface of above-mentioned anti-reflection layer (low-index layer) also can form lubricating layer.Lubricating layer is given the low-refraction laminar surface with slickness, has the function of improving scoring resistance.Lubricating layer can use polysiloxane (for example silicone oil), natural wax, pertroleum wax, higher fatty acid slaine, fluorine containing lubricant or its derivant to form.The thickness of lubricating layer is preferably 2～20nm.
When in light filter, containing the compound of representing by above-mentioned general formula (I) of the present invention; Under the situation that adopts above-mentioned " (3) are being selected from the method that contains in any adjacent adhesive phase between the two in transparent supporting body and any each layer "; Can in bonding agent, contain compound of the present invention etc.; Use this bonding agent then, carry out adjacent both among above-mentioned transparent supporting body and any each layer bonding.As this bonding agent, can use known suitable glass such as bonding agents such as silicone, urethanes, acrylic compounds, polyvinyl butyral class bonding agent, ethylene-vinyl acetate class bonding agent to use clear binder.In addition, when using this bonding agent, can use crosslinking chemicals such as metallo-chelate class, isocyanates, epoxies as hardening agent as required.In addition, the thickness of adhesive phase is preferably 2～400 μ m.
When above-mentioned when adopting " (4) and each layer arbitrarily are provided with the method for the light absorbing zone of light absorbers such as containing compound of the present invention etc. dividually "; Can directly use compound of the present invention to form light absorbing zone, it is scattered in forms light absorbing zone in the bonding agent.As this bonding agent, for example can use synthesized polymer materials such as natural macromolecular material such as gelatin, casein, starch, cellulose derivative, alginic acid or polymethylmethacrylate, polyvinyl butyral, polyvinyl pyrrolidone, polyvinyl alcohol (PVA), PVC, SB, polystyrene, polycarbonate, polyamide.
When using above-mentioned bonding agent, also can be with an organic solvent simultaneously, as this organic solvent, known all kinds of solvents can not suitably be used in not special restriction, for example can enumerate out alcohols such as isopropyl alcohol; Ether alcohol classes such as methyl cellosolve, ethyl cellosolve, butyl cellosolve, butyldiglycol; Ketones such as acetone, MEK, methyl isobutyl ketone, cyclohexanone, DAA; Ester classes such as ethyl acetate, butyl acetate, acetic acid methoxyl ethyl ester; Esters of acrylic acid such as ethyl acrylate, butyl acrylate; 2,2,3,3-tetrafluoropropanol etc. is fluoridized alcohols; Hydro carbons such as hexane, benzene,toluene,xylene; Chlorinated hydrocarbons such as methylene chloride, ethylene dichloride, chloroform etc.These organic solvents can use or mix use separately.
In addition, above-mentioned undercoat, anti-reflection layer, hard conating, lubricating layer, filter layer etc. can use common coating method to form.As coating method, can enumerate out rod and be coated with method, dip coating, identical (kiss) coating process, spraying process, air knife coating process, curtain coating, rolling method, coiling rod coating process, gravure coating method, scraper plate coating process, lip (lip) coating process, use the extrusion coating method (No. 2681294 instructions record of United States Patent (USP)) of funnel etc.Also can form two-layer above layer through applying simultaneously.About the while coating method, on the books in No. the 2761791st, United States Patent (USP), No. the 2941898th, United States Patent (USP), No. the 3508947th, United States Patent (USP), No. 3526528 each instructions of United States Patent (USP) and former rugged brave work " コ one テ イ Application グ engineering " 253 pages (1973 towards the distribution of storehouse bookstore).
Embodiment
Below, utilize manufacturing example, embodiment and comparative example to come to explain in further detail the present invention.But the present invention does not receive any restrictions such as following examples.
Making example 1 is expression compound N manufacturing example o.1.And, even for other compound that uses among the embodiment 6～16 by above-mentioned general formula (I) expression, also can be synthetic according to above-mentioned synthetic method.
The making example of the light filter of the present invention of the compound that is obtained by manufacturing example 1 has been used in embodiment 1～5 expression; The making example by the light filter of the present invention of other compounds of above-mentioned general formula (I) expression has been used in embodiment 6～16 expressions, and the making example of the comparison light filter of comparative compound has been used in comparative example 1 expression.
O.1 synthetic of [make example 1] compound N
In the reaction flask that has carried out nitrogen replacement, pack into diethyl amino benzaldehyde 328g (1.85mol), ethyl cyanoacetate 251 g (2.22mol) and ethanol 500g drip triethylamine 18.7g (0.189mol) down at 50 ℃, and heated 2.5 hours down at 70 ℃.Be cooled to room temperature, leach the solid of separating out then.Use washing with alcohol, pass through drying under reduced pressure then, obtain orange solids 467g (yield 93%).Confirm that as the compound N of object o.1 the orange solids obtain is.Analysis result to the orange solids that obtains is following.
(analysis result)
(1) 1H-NMR (DMSO solvent)
(the chemical displacement value ppm of summit; Multiplicity; Proton number)
(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 absorptiometry (chloroform solvent)
λmax：429.5nm，ε：5.50×10 4
(3) decomposition temperature (TG-DTA: in 100ml/ minute nitrogen flowed, programming rate was 10 ℃/minute)
96.9 ℃; Fusing point: 272.5 ℃; Summit
The making 1 of [embodiment 1] light filter
Prescription modulation according to following applies liquid; On the thick polyethylene terephthalate thin film of the 188 μ m that carried out easy adhesion process; After being coated with machine #9 and applying this coating liquid with rod; 100 ℃ dry 3 minutes down, be about the light filter of 10 microns thin layer (compound N content o.1 be 2.0mg/m thereby obtain on polyethylene terephthalate thin film, to have thickness 2).For this light filter, V-570 measures its absorption spectrum with Japanese beam split (strain) system UV, visible light near infrared spectrometer, and the result is that max is 430nm, and half value is wide to be 47nm.
(prescription)
スミペツ?ク?ス?LG?2.5g
(Sumitomo Chemical (strain) system acrylic adhesive, resin portion is divided into 40 quality %)
Compound N is 2mg o.1
MEK 2.5g
The making 2 of [embodiment 2] light filter
According to following prescription modulating adhesive solution; On the thick polyethylene terephthalate thin film of the 188 μ m that carried out easy adhesion process; After being coated with machine #30 and applying this binder solution with rod; 100 ℃ dry 10 minutes down, (compound N content o.1 is 2.0mg/m thereby obtain on polyethylene terephthalate thin film, to have the light filter of thick about 10 microns adhesive phase 2).For this light filter, V-570 measures with Japanese beam split (strain) system UV, visible light near infrared spectrometer, and the result is that λ max is 429nm, and half value is wide to be 48nm.
(prescription)
Compound N is 2.0mg o.1
Acrylic adhesives 20g
(デ one PVC one ボ Application De 5541: ダ イ ア ボ Application De society system)
MEK 80g
The making 3 of [embodiment 3] light filter
With PLASTOMILL (プ ラ ス ト ミ Le) muller at 260 ℃ with following prescription melting mixing 5 minutes.After the mixing, extruded by the nozzle of diameter 6mm, water cooling granulation machine obtains to contain the particle of pigment.This particle working voltage machine is configured as the thick thin plate of 0.25mm at 250 ℃, and (compound N content o.1 is 2.0mg/m 2).For this thin plate, V-570 measures its absorption spectrum with Japanese beam split (strain) system UV, visible light near infrared spectrometer, and the result is that λ max is 429.5nm, and half value is wide to be 47.5nm.
(prescription)
ユ one ピ ロ Application S-3000 100g
(Mitsubishi's gas chemistry (strain) system; Polycarbonate resin)
Compound N is 0.01g o.1
The making 4 of [embodiment 4] light filter
According to following prescription modulation UV varnish, on the thick polyethylene terephthalate thin film of the 188 μ m that carried out easy adhesion process, after being coated with machine #9 and applying this UV varnish with rod, 80 ℃ of following dry 30 seconds.Then, with having the high voltage mercury lamp radiation 100mJ ultraviolet ray that infrared ray cuts off film filter, obtain to have and solidify thickness and be about the light filter of 5 microns filter layer (compound N content o.1 is 2.0mg/m 2).For this light filter, V-570 measures its absorption spectrum with Japanese beam split (strain) system UV, visible light near infrared spectrometer, and the result is that λ max is 429.5m, and half value is wide to be 47.6nm.
(prescription)
ア デ カ オ プ ト マ one KRX-571-65 100g
(rising sun electrochemical industry (strain) system UV cured resin, resin portion is divided into 80 quality %)
Compound N is 0.5g o.1
MEK 60g
The making 5 of [embodiment 5] light filter
Prescription modulation according to following applies liquid; On the thick polyethylene terephthalate thin film of the 188 μ m that carried out easy adhesion process; After being coated with machine #9 and applying this coating liquid with rod; Drying is 3 minutes under 100 ℃, thereby obtains on polyethylene terephthalate thin film, to have light filter (the compound N content 2.0mg/m o.1 that thickness is about 10 microns thin layer 2).For this light filter, V-570 measures with Japanese beam split (strain) system UV, visible light near infrared spectrometer, and the result is that λ max is 430nm, and half value is wide to be 47nm.
(prescription)
Port リ エ ス タ one TP-220 100g
(Japanese synthetic chemistry system vibrin)
Compound N is 1.0g o.1
MEK 60g
The making 6～16 of [embodiment 6～16] light filter
Except the compound N that uses 2mg respectively o.3, No.4, No.7～No.11, No.13～16 replace 2mg compound N o.1; Make light filter with embodiment 1 identically; Light filter to obtaining is measured with Japanese beam split (strain) system UV, visible light near infrared spectrometer V-570, and the result is shown in [table 1].
[table 1]
Compound λmax(nm) Half value wide (nm)
Embodiment 6 Compound N o.3 437.0 46.5
Embodiment 7 Compound N o.4 433.0 49.5
Embodiment 8 Compound N o.7 415.0 47.0
Embodiment 9 Compound N o.8 434.0 47.0
Embodiment 10 Compound N o.9 441.5 47.5
Embodiment 11 Compound N o.10 435.0 48.5
Embodiment 12 Compound N o.11 448.5 48.0
Embodiment 13 Compound N o.13 434.0 49.0
Embodiment 14 Compound N o.14 439.5 48.5
Embodiment 15 Compound N o.15 392.0 49.5
Embodiment 16 Compound N o.16 402.5 49.5
[comparative example 1] be the making 1 of light filter relatively
The compound N that replaces 2mg except the comparative compound No.1 that uses 2.4mg o.1; Make light filter with embodiment 1 identically; Light filter to obtaining is measured with Japanese beam split (strain) system UV, visible light near infrared spectrometer V-570; The result is that λ max is 354nm, and half value is wide to be 92nm.
Figure G200710096106620070423D000181
(380～500nm) locate there is not maximum absorption wavelength, and half value is roomy, and the light that might need also is absorbed because the light filter of comparative example 1 is at specific wavelength.In contrast; Used the light filter of the embodiment 1～16 of cyanine compound of the present invention (380～500nm) to locate to have sharp-pointed absorption (half value wide as 50nm below), show as image display device, particularly plasma scope plate with the excellent performance of light filter at specific wavelength.

Claims (5)

1. light filter, it forms through containing at least a compound by formula (I) expression,
Figure FSB00000828133400011
In the formula, R 1Expression hydrogen atom, methyl, ethyl or propyl group, wherein, the methylene in methyl, ethyl, the propyl group also can be replaced by-O-; R 2The expression hydrogen atom; R 3Expression can have substituent amino, and said substituting group is methyl, ethyl or propyl group; R 4And R 5Represent hydrogen atom respectively independently; R 6The expression cyanic acid or-COOR, wherein R representes hydrogen atom, methyl, ethyl or propyl group.
2. light filter, it forms through any that contains in the following compound,
Figure FSB00000828133400021
Claim 1 or 2 the record light filter, wherein per unit area contains 1～1000mg/m 2Said compound.
4. the light filter of any one record of claim 1～3, it is used for image display device.
5. the light filter of claim 4 record, wherein said image display device is a plasma scope.
CN2007100961066A 2006-04-13 2007-04-13 Light filter Expired - Fee Related CN101055328B (en)

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