JP2008250022A - Optical filter - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an optical filter which has steep light absorptions in respective wavelength regions of 200-450 nm, 450-750 nm, and 750-1,100 nm, and which is suitable for an image display device. <P>SOLUTION: The optical filter is characterized in that it includes at least a kind of cyanine compound represented by general formula (I). <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

The present invention relates to an optical filter containing a cyanine compound having a specific molecular structure. The cyanine compound is particularly useful as a light absorber to be contained in an optical filter for an image display device.

Compounds having strong absorption in the wavelength range of 450 nm to 1100 nm, particularly compounds having a maximum absorption (λmax) in the range of 550 to 620 nm, are used for optical recording layers of optical recording media such as DVD ± R, and liquid crystal display devices (LCD). It is used as an optical element in an optical filter for an image display device such as a plasma display panel (PDP), an electroluminescence display (ELD), a cathode ray tube display (CRT), a fluorescent display tube, or a field emission display.

For example, as an application of the optical element in the image display device, there is a light absorber for a color filter. The image display device displays a color image with a combination of light of the three primary colors of red, blue, and green. However, the display quality of the light that displays the color image is deteriorated such as 550 to 620 nm between green and red. In addition, light that causes malfunction of an infrared remote controller of 750 to 1100 nm is also included. The optical filter is required to have a function of selectively absorbing light of the above-described unnecessary wavelength, and at the same time, in order to prevent reflection and reflection of external light from a fluorescent lamp or the like, 480 to 500 nm and 540 to 560 nm. It is also necessary to absorb light having a wavelength of 300 to 390 nm as an ultraviolet absorber. Therefore, an optical filter containing a light-absorbing compound (light absorber) that selectively absorbs light of these wavelengths is used in an image display device or the like.

Further, in recent years, a light absorber that selectively absorbs a wavelength of 450 to 800 nm is also demanded in order to achieve sufficient color purity and color separation of the display element and to improve image quality. These light absorbers are required to have particularly steep light absorption, that is, having a small half-value width of λmax and not to lose its function due to light, heat, or the like.

As an optical filter containing a light absorber, for example, the following Patent Document 1 discloses an optical filter using a cyanine compound having a maximum absorption wavelength at 560 to 620 nm. An optical filter using an azaporphyrin compound having a maximum absorption wavelength at 605 nm is disclosed, and the following Patent Document 3 discloses an optical filter using a condensed polycyclic pigment having a maximum absorption wavelength at 551 to 600 nm. Patent Document 4 below discloses an optical filter using a cyanine compound having a maximum absorption wavelength at 540 to 560 nm.
Moreover, as an optical filter using an ultraviolet absorber, for example, Patent Document 5 below reports an organic EL display element filter that contains an ultraviolet absorber and blocks light of 200 to 410 nm.
In addition, as an optical filter containing a light absorber that selectively absorbs light having an unnecessary wavelength of 750 to 1100 nm, for example, in Patent Document 6 below, a cyanine compound and a diimonium compound having a specific structure are essential components. A near-infrared absorbing film having a near-infrared absorbing layer is disclosed, and Patent Document 7 below discloses a near-infrared absorbing optical filter containing a metal complex having a specific structure.
Patent Document 8 below discloses an optical recording material using a cyanine compound, but does not describe or suggest that the cyanine compound can be used in an optical filter.

JP 2002-148430 A JP 2003-57437 A JP 2004-310072 A JP 2005-331545 A JP 2004-102223 A JP 2002-350632 A JP 2005-99755 A Japanese Patent Application Laid-Open No. 11-53761

Accordingly, an object of the present invention is to provide an optical filter that has steep light absorption in each of the wavelength regions of 200 to 450 nm, 450 to 750 nm, and 750 to 1100 nm, and is particularly suitable for an image display device.

As a result of various studies, the present inventors have found that a cyanine compound having a specific molecular structure has sharp light absorption in a specific wavelength region and can significantly improve the image characteristics of an image display device. did. Further, since the cyanine compound has high solubility and durability in an organic solvent and has a high ε, the amount used when added to an optical filter can be reduced, so that the cost can be reduced.

The present invention has been made based on the above findings, and has achieved the above object by providing an optical filter comprising at least one cyanine compound represented by the following general formula (I): It is.

（式中、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５及びＲ^６は、それぞれ独立に、炭素原子数１〜１０のアルキル基、炭素原子数６〜３０のアリール基、炭素原子数７〜３０のアリールアルキル基又は下記一般式（II）で表される置換基を表し、Ｒ^３とＲ^４、及びＲ^５とＲ^６は、互いに結合して環構造を形成していてもよく、Ｒ^２１、Ｒ^２２及びＲ^２３は、それぞれ独立に、水素原子、水酸基、ハロゲン原子、シアノ基、ジフェニルアミノ基、炭素原子数１〜１０のアルキル基、炭素原子数６〜３０のアリール基又は炭素原子数７〜３０のアリールアルキル基を表し、該アルキル基又はアリールアルキル基のアルキレン部分は、−Ｏ−、−Ｓ−、−ＣＯ−、−ＣＯＯ−、−ＯＣＯ−、−ＣＨ＝ＣＨ−、−ＮＨＣＯ−又は−ＣＯＮＨ−で置換されていてもよく、Ｒ^２１、Ｒ^２２及びＲ^２３のうち、隣接する置換基は互いに結合して環構造を形成していてもよい。ｎは、０、２又は３であり、Ａｎ^ｑ−はｑ価のアニオンを表し、ｑは１又は２であり、ｐは電荷を中性に保つ係数を表す。）

(Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are each independently an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or the number of carbon atoms. 7 to 30 arylalkyl groups or a substituent represented by the following general formula (II), R ³ and R ⁴ , and R ⁵ and R ⁶ may be bonded to each other to form a ring structure. , R ²¹ , R ²² and R ²³ are each independently a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group, a diphenylamino group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or Represents an arylalkyl group having 7 to 30 carbon atoms, and the alkyl group or the alkylene portion of the arylalkyl group is -O-, -S-, -CO-, -COO-, -OCO-, -CH = CH- , -NHCO- or -CONH- May also ^be, among of R ^{21, R 22} and ^{R 23,} the substituent adjacent optionally form a ring structure together .n is 0,2 or 3, ^{An q-} Represents a q-valent anion, q is 1 or 2, and p represents a coefficient for maintaining a neutral charge.)

（式中、Ｒ^ａ〜Ｒ^ｉは、各々独立に、水素原子又は炭素原子数１〜４のアルキル基を表し、該アルキル基中のメチレン基は、−Ｏ−又は−ＣＯ−で置換されていてもよく、Ｚ^１は、直接結合又は炭素原子数１〜８のアルキレン基を表し、該アルキレン基中のメチレン基は、−Ｏ−、−Ｓ−、−ＣＯ−、−ＣＯＯ−、−ＯＣＯ−、−ＳＯ_２−、−ＮＨ−、−ＣＯＮＨ−、−ＮＨＣＯ−、−Ｎ＝ＣＨ−又は−ＣＨ＝ＣＨ−で置換されていてもよく、Ｍは、Ｆｅ、Ｃｏ、Ｎｉ、Ｔｉ、Ｃｕ、Ｚｎ、Ｚｒ、Ｃｒ、Ｍｏ、Ｏｓ、Ｍｎ、Ｒｕ、Ｓｎ、Ｐｄ、Ｒｈ、Ｐｔ又はＩｒを表す。）

(Wherein R ^{a to} R ⁱ each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the methylene group in the alkyl group is substituted with —O— or —CO—). Z ¹ represents a direct bond or an alkylene group having 1 to 8 carbon atoms, and the methylene group in the alkylene group is -O-, -S-, -CO-, -COO-, -OCO. —, —SO ₂ —, —NH—, —CONH—, —NHCO—, —N═CH— or —CH═CH— may be substituted, and M is Fe, Co, Ni, Ti, Cu. , Zn, Zr, Cr, Mo, Os, Mn, Ru, Sn, Pd, Rh, Pt or Ir.)

The present invention also provides an optical filter comprising at least one compound having a maximum absorption at 550 to 620 nm in at least one cyanine compound represented by the general formula (I). The above-mentioned purpose has been achieved.

The cyanine compound represented by the above general formula (I) contained in the optical filter of the present invention has a high ε and exhibits steep light absorption in a specific wavelength region of 300 to 1100 nm. Further, it is effective for quenching the fluorescence of the cyanine compound represented by the general formulas (VI) and (VII). Therefore, the optical filter of the present invention containing the cyanine compound is an optical filter suitable for image display applications, particularly plasma display applications.

Hereinafter, preferred embodiments of the optical filter of the present invention will be described in detail.
First, the cyanine compound represented by the general formula (I) will be described.
Examples of the alkyl group having 1 to 10 carbon atoms represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ²¹ , R ²² and R ²³ in the general formula (I) include methyl , Ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, hexyl, cyclohexyl, heptyl, isoheptyl, tert-heptyl, n-octyl, isooctyl, tert-octyl, 2 - ^ethylhexyl. Examples ^of the ^{R 1, R 2, R 3} , R 4, R 5, R 6, R 21, aryl group having 6 to 30 carbon atoms represented by ^{R 22} and ^{R 23,} phenyl , naphthyl, anthracene-1-yl, phenanthrene-1-yl and the ^{like, R 1, R 2, R} 3, R 4, R 5, R 6, R 21, R 22 and The aryl alkyl group having 7 to 30 carbon atoms represented by ^23, benzyl, phenethyl, 2-phenylpropane, diphenylmethyl, triphenylmethyl, styryl, cinnamyl and the ^like, R ^{21, R 22} and ^{R 23} Examples of the halogen atom represented by the formula include fluorine, chlorine, bromine and iodine.

In the general formula (I), the ring structure formed by combining adjacent substituents among R ³ and R ⁴ , R ⁵ and R ^{6 and} R ²¹ , R ²² and R ²³ is a cyclopropane ring, Cyclobutane ring, cyclopentane ring, cyclohexane ring, benzene ring, naphthalene ring, furan ring, thiophene ring, pyrrole ring, tetrahydropyran ring, piperidine ring, piperazine ring, pyrrolidine ring, morpholine ring, thiomorpholine ring, pyridine ring, Examples include pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, quinoline ring, isoquinoline ring, thiazole ring, imidazole ring, oxazole ring, imidazolidine ring, pyrazolidine ring, isoxazolidine ring, isothiazolidine ring, etc. It may be fused or substituted with other rings.

A C 1-10 alkyl group represented by R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ²¹ , R ²² and R ²³ , R ¹ , R ² , R ³ , R ⁴ , an aryl group having 6 to 30 carbon atoms represented by R ⁵ , R ⁶ , R ²¹ , R ²² and R ²³ , and R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ^21. Any of the arylalkyl groups having 7 to 30 carbon atoms represented by R ²² and R ²³ may have a substituent. Examples of the substituent include the following. R ^{1 to} R ⁶ and R ²¹ , R ²² and R ²³ are groups containing a carbon atom such as the above alkyl group having 1 to 10 carbon atoms, and these groups are substituted as follows: Among the groups, when having a substituent containing a carbon atom, the total number of carbon atoms of R ^{1 to} R ⁶ and R ²¹ , R ²² and R ²³ including the substituent satisfies the specified range. And
Examples of the substituent include methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, cyclopentyl, hexyl, 2-hexyl, and 3-hexyl. , Alkyl groups such as cyclohexyl, bicyclohexyl, 1-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, tertiary heptyl, n-octyl, isooctyl, tertiary octyl, 2-ethylhexyl, nonyl, isononyl, decyl Methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, sec-butyloxy, tert-butyloxy, isobutyloxy, amyloxy, isoamyloxy, tert-amyloxy, hexyloxy, cyclohexyloxy, hex Alkoxy groups such as tiloxy, isoheptyloxy, tertiary heptyloxy, n-octyloxy, isooctyloxy, tertiary octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy; methylthio, ethylthio, propylthio, isopropylthio, butylthio, Dibutylthio, tert-butylthio, isobutylthio, amylthio, isoamylthio, tert-amylthio, hexylthio, cyclohexylthio, heptylthio, isoheptylthio, tert-heptylthio, n-octylthio, isooctylthio, tert-octylthio, 2-ethylhexylthio, etc. Alkylthio group; vinyl, 1-methylethenyl, 2-methylethenyl, 2-propenyl, 1-methyl-3-propenyl, 3-butenyl, 1-methyl-3-butenyl, isobutenyl , Alkenyl groups such as 3-pentenyl, 4-hexenyl, cyclohexenyl, bicyclohexenyl, heptenyl, octenyl, decenyl, pentadecenyl, eicosenyl, tricocenyl; arylalkyl groups such as benzyl, phenethyl, diphenylmethyl, triphenylmethyl, styryl, cinnamyl Aryl groups such as phenyl and naphthyl; aryloxy groups such as phenoxy and naphthyloxy; arylthio groups such as phenylthio and naphthylthio; , Triazolyl, furyl, furanyl, benzofuranyl, thienyl, thiophenyl, benzothiophenyl, thiadiazolyl, thiazolyl, Benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, indolyl, 2-pyrrolidinon-1-yl, 2-piperidone-1-yl, 2,4-dioxyimidazolidin-3-yl, 2,4-dioxy Heterocyclic groups such as oxazolidin-3-yl; halogen atoms such as fluorine, chlorine, bromine, iodine; acetyl, 2-chloroacetyl, propionyl, octanoyl, acryloyl, methacryloyl, phenylcarbonyl (benzoyl), phthaloyl, 4-trifluoro Acyl groups such as methylbenzoyl, pivaloyl, salicyloyl, oxaloyl, stearoyl, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, n-octadecyloxycarbonyl, carbamoyl; acetyloxy, benzoylo Acyloxy groups such as bis; amino, ethylamino, dimethylamino, diethylamino, butylamino, cyclopentylamino, 2-ethylhexylamino, dodecylamino, anilino, chlorophenylamino, toluidino, anisidino, N-methyl-anilino, diphenylamino, naphthylamino 2-pyridylamino, methoxycarbonylamino, phenoxycarbonylamino, acetylamino, benzoylamino, formylamino, pivaloylamino, lauroylamino, carbamoylamino, N, N-dimethylaminocarbonylamino, N, N-diethylaminocarbonylamino, morpholinocarbonylamino , Methoxycarbonylamino, ethoxycarbonylamino, t-butoxycarbonylamino, n-octadecyloxycarbo Substituted amino groups such as ruamino, N-methyl-methoxycarbonylamino, phenoxycarbonylamino, sulfamoylamino, N, N-dimethylaminosulfonylamino, methylsulfonylamino, butylsulfonylamino, phenylsulfonylamino; sulfonamide group, sulfonyl Group, carboxyl group, cyano group, sulfo group, hydroxyl group, nitro group, mercapto group, imide group, carbamoyl group, sulfonamide group and the like, and these groups may be further substituted. Moreover, the carboxyl group and the sulfo group may form a salt.

In the general formula (I), the anion represented by An ^q- is, for example, a monovalent halogen anion such as a chlorine anion, a bromine anion, an iodine anion, a fluorine anion; a perchlorate anion, a chloric acid Inorganic anions such as anion, thiocyanate anion, hexafluorophosphate anion, antimony hexafluoride anion, boron tetrafluoride anion; benzenesulfonate anion, toluenesulfonate anion, trifluoromethanesulfonate anion, diphenylamine-4- Sulfonic acid anion, 2-amino-4-methyl-5-chlorobenzenesulfonic acid anion, 2-amino-5-nitrobenzenesulfonic acid anion, JP-A-8-253705, JP-T-2004-503379, JP-A-2005-2005 No. 336150, country Organic sulfonate anions such as sulfonate anions described in JP 2006/28006 A, etc .; octyl phosphate anion, dodecyl phosphate anion, octadecyl phosphate anion, phenyl phosphate anion, nonylphenyl phosphate anion, 2,2 ′ -Organic phosphate anions such as methylenebis (4,6-ditert-butylphenyl) phosphonate anion, bistrifluoromethylsulfonylimide anion, bisperfluorobutanesulfonylimide anion, perfluoro-4-ethylcyclohexanesulfonate anion, tetrakis (Pentafluorophenyl) borate anion, tetrakis (pentafluorophenyl) gallium anion, tris (fluoroalkylsulfonyl) carbanion, dibenzoyl tartrate anion, etc. As those of valence, such as benzene disulfonic acid anion and naphthalene disulfonic acid anion. In addition, quencher anions that have the function of de-exciting (quenching) active molecules in the excited state, and ferrocene and luteocene having an anionic group such as a carboxyl group, a phosphonic acid group, and a sulfonic acid group on the cyclopentadienyl ring. A metallocene compound anion such as can also be used as necessary.

Examples of the quencher anion include those represented by the following general formulas (A) and (B) or the following formulas (C) and (D), JP-A-60-234892, and JP-A-5-43814. JP-A-5-305770, JP-A-6-239028, JP-A-9-309886, JP-A-9-323478, JP-A-10-45767, JP-A-11-208118 JP-A-2000-168237, JP-A-2002-201373, JP-A-2002-206061, JP-A-2005-297407, JP-B-7-96334, WO98 / 29257, International Examples include anions such as those described in JP 2006/123786 A.

（式中、Ｍは、ニッケル原子、コバルト原子又は銅原子を表し、Ｒ^１０及びＲ^１１は、ハロゲン原子、炭素原子数１〜８のアルキル基、炭素原子数６〜３０のアリール基又は−ＳＯ_２−Ｇ基を表し、Ｇは、アルキル基、ハロゲン原子で置換されていてもよいアリール基、ジアルキルアミノ基、ジアリールアミノ基、ピペリジノ基又はモルフォリノ基を表し、ａ及びｂは、それぞれ独立に、０〜４の数を表す。また、Ｒ^１２、Ｒ^１３、Ｒ^１４及びＲ^１５は、各々独立にアルキル基、アルキルフェニル基、アルコキシフェニル基又はハロゲン化フェニル基を表す。）

(In the formula, M represents a nickel atom, a cobalt atom, or a copper atom, and R ¹⁰ and R ¹¹ represent a halogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 30 carbon atoms, or —SO 2. _2- G group, G represents an alkyl group, an aryl group optionally substituted with a halogen atom, a dialkylamino group, a diarylamino group, a piperidino group or a morpholino group, and a and b are each independently And represents a number of 0 to 4. R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ each independently represents an alkyl group, an alkylphenyl group, an alkoxyphenyl group or a halogenated phenyl group.

Among the cyanine compounds represented by the above general formula (I), those represented by the following general formulas (III) to (V) are preferable because they are highly soluble in organic solvents and can be synthesized at low cost.

（式中、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｒ^６、Ｒ^２３、Ａｎ^ｑ−、ｑ及びｐは、上記一般式（Ｉ）と同じである。）

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ²³ , An ^q− , q and p are the same as those in the general formula (I).)

（式中、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｒ^６、Ｒ^２１、Ｒ^２２、Ｒ^２３、Ａｎ^ｑ−、ｑ及びｐは、上記一般式（Ｉ）と同じであり、Ｒ^２１、Ｒ^２２及びＲ^２３は、互いに異なっていてもよく、隣接する置換基が連結して環構造を形成していてもよい。）

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ²¹ , R ²² , R ²³ , An ^q− , q and p are the same as those in the general formula (I). , R ²¹ , R ²² and R ²³ may be different from each other, and adjacent substituents may be linked to form a ring structure.)

（式中、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｒ^６、Ｒ^２１、Ｒ^２２、Ｒ^２３、Ａｎ^ｑ−、ｑ及びｐは、上記一般式（Ｉ）と同じであり、Ｒ^２１、Ｒ^２２及びＲ^２３は、互いに異なっていてもよく、隣接する置換基が連結して環構造を形成していてもよい。）
上記一般式（IV）及び（Ｖ）中のＲ^２１、Ｒ^２２及びＲ^２３は、隣接する置換基と互いに連結して環構造を形成していてもよく、該環構造としては、例えば、シクロペンテン環、シクロヘキセン環、ベンゼン環、ナフタレン環、フェナントレン環、ピリジン環、ピラジン環、ピリミジン環、ピリダジン環、ユロリジン環、トリアジン環、キノリン環、イソキノリン環、イミダゾール環、オキサゾール環、イミダゾリジン環、ピラゾリジン環、イソオキサゾリジン環、イミノオキサゾリジン環、イソチアゾリジン環、ロダニン環、チオオキサゾリドン環、チオヒダントイン環、インダンジオン環、チアナフテン環、ピラゾロン環、ピリドン環、ピラゾリジンジオン環、バルビツール酸環、チオバルビツール酸環、オキサゾロン環、ヒダントイン環、チオヒダントイン環、スクシンイミド環、マレイミド環等が挙げられ、これらの環は他の環と縮合されていたり、置換されていたりしてもよい。
上記一般式（III）〜(Ｖ)で表される本発明に係るシアニン化合物の好ましい具体例としては、下記化合物Ｎｏ．１〜３６が挙げられる。尚、以下の例示では、アニオンを省いたカチオンで示している。本発明に係るシアニン化合物において、ポリメチン鎖は共鳴構造をとっていてもよく、またカチオンがもう一方の複素環骨格中の窒素原子上にあってもよい。

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ²¹ , R ²² , R ²³ , An ^q− , q and p are the same as those in the general formula (I). , R ²¹ , R ²² and R ²³ may be different from each other, and adjacent substituents may be linked to form a ring structure.)
R ²¹ , R ²² and R ²³ in the above general formulas (IV) and (V) may be linked to adjacent substituents to form a ring structure. Examples of the ring structure include cyclopentene, Ring, cyclohexene ring, benzene ring, naphthalene ring, phenanthrene ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, urolidine ring, triazine ring, quinoline ring, isoquinoline ring, imidazole ring, oxazole ring, imidazolidine ring, pyrazolidine ring , Isoxazolidine ring, iminooxazolidine ring, isothiazolidine ring, rhodanine ring, thiooxazolidone ring, thiohydantoin ring, indandione ring, thianaphthene ring, pyrazolone ring, pyridone ring, pyrazolidinedione ring, barbituric acid ring, thiobarbi Tool acid ring, oxazolone ring, hydantoy Ring, thiohydantoin ring, a succinimide ring, a maleimide ring, and these rings or be fused with other ring or may or substituted.
Preferable specific examples of the cyanine compound according to the present invention represented by the general formulas (III) to (V) are the following compound Nos. 1-36 is mentioned. In the following examples, the anion is shown as a cation. In the cyanine compound according to the present invention, the polymethine chain may have a resonance structure, and the cation may be on a nitrogen atom in the other heterocyclic skeleton.

In the optical filter of the present invention, a wavelength of 450 to 750 nm is selected by using at least one compound having a maximum absorption in the range of 550 to 620 nm as at least one of the cyanine compounds represented by the general formula (I). Can be absorbed.
The compound having the maximum absorption in the range of 550 to 620 nm is not particularly limited, and is a trimethine cyanine derivative, squarylium dye derivative, azomethine dye derivative, xanthene dye derivative, azo dye derivative, oxonol dye derivative, benzylidene dye derivative, pyromethene. Dye derivatives, azo metal complex derivatives, rhodamine dye derivatives, phthalocyanine derivatives, porphyrin derivatives, dipyrromethene metal chelate compounds, and the like can be used. Among them, cyanine compounds represented by the following general formulas (VI) to (VIII) are preferable. .

（式中、Ｒ^１、Ｒ^２、Ｒ^３、Ｒ^４、Ｒ^５、Ｒ^６、Ｒ^２１、Ｒ^２２、Ｒ^２３、Ａｎ^ｑ−、ｑ及びｐは、上記一般式（Ｉ）と同じである。）

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ²¹ , R ²² , R ²³ , An ^q− , q and p are the same as those in the general formula (I). .)

（式中、Ｒ^３０及びＲ^３１は、それぞれ独立に、水素原子、水酸基、ハロゲン原子、ニトロ基、シアノ基、炭素原子数１〜１０のアルキル基、炭素原子数６〜３０のアリール基、炭素原子数７〜３０のアリールアルキル基又は上記一般式（II）で表される置換基を表し、Ｒ^３２、Ｒ^３３及びＲ^３６は、それぞれ独立に、水素原子、炭素原子数１〜１０のアルキル基、炭素原子数６〜３０のアリール基、炭素原子数７〜３０のアリールアルキル基又は上記一般式（II）で表される置換基を表し、Ｒ^３４及びＲ^３５は、それぞれ独立に、水素原子、炭素原子数１〜１０のアルキル基、炭素原子数６〜３０のアリール基、炭素原子数７〜３０のアリールアルキル基又は上記一般式（II）で表される置換基を表し、Ｒ^３４とＲ^３５は、互いに結合して環構造を形成していてもよい。該アルキル基又はアリールアルキル基のアルキレン部分は、−Ｏ−、−Ｓ−、−ＣＯ−、−ＣＯＯ−、−ＯＣＯ−、−ＣＨ＝ＣＨ−、−ＮＨＣＯ−又は−ＣＯＮＨ−で置換されていてもよい。ｓ及びｔは、それぞれ独立に、１〜４の数であり、Ａｎ^ｑ−、ｑ及びｐは、上記一般式（Ｉ）と同じである。）

(Wherein R ³⁰ and R ³¹ are each independently a hydrogen atom, hydroxyl group, halogen atom, nitro group, cyano group, alkyl group having 1 to 10 carbon atoms, aryl group having 6 to 30 carbon atoms, carbon Represents an arylalkyl group having 7 to 30 atoms or a substituent represented by the above general formula (II), wherein R ³² , R ³³ and R ³⁶ each independently represent a hydrogen atom or an alkyl having 1 to 10 carbon atoms; Group, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a substituent represented by the above general formula (II), wherein R ³⁴ and R ³⁵ are each independently hydrogen represents atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, a substituent represented by an arylalkyl group or the general formula -C 7~30 ^{(II), R 34} And R ³⁵ are bonded to each other The alkylene group of the alkyl group or arylalkyl group may be —O—, —S—, —CO—, —COO—, —OCO—, —CH═CH—, -NHCO- or -CONH- may be substituted, s and t are each independently a number of 1 to 4, and An ^q- , q and p are the same as those in the general formula (I). is there.)

（式中、Ｒ^３７は、水素原子、水酸基、ハロゲン原子、シアノ基、ニトロ基、炭素原子数１〜１０のアルキル基、炭素原子数６〜３０のアリール基、炭素原子数７〜３０のアリールアルキル基又は上記一般式（II）で表される置換基を表し、Ｒ^３８及びＲ^３９は、それぞれ独立に、水素原子、炭素原子数１〜１０のアルキル基、炭素原子数６〜３０のアリール基、炭素原子数７〜３０のアリールアルキル基、ハロゲン原子、ニトロ基、シアノ基又は上記一般式（II）で表される置換基を表し、該アルキル基又はアリールアルキル基のアルキレン部分は、−Ｏ−、−Ｓ−、−ＣＯ−、−ＣＯＯ−、−ＯＣＯ−、−ＣＨ＝ＣＨ−、−ＮＨＣＯ−又は−ＣＯＮＨ−で置換されていてもよい。ｄは、１〜４の数であり、Ａｎ^ｑ−、ｑ及びｐは、上記一般式（Ｉ）と同じである。）

(In the formula, R ³⁷ represents a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aryl having 7 to 30 carbon atoms. Represents an alkyl group or a substituent represented by the general formula (II), and R ³⁸ and R ³⁹ each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl having 6 to 30 carbon atoms. Group, an arylalkyl group having 7 to 30 carbon atoms, a halogen atom, a nitro group, a cyano group, or a substituent represented by the above general formula (II), and the alkylene portion of the alkyl group or arylalkyl group is- O—, —S—, —CO—, —COO—, —OCO—, —CH═CH—, —NHCO— or —CONH— may be substituted, and d is a number from 1 to 4. , ^{An q-,} q and p are the General formula (I) which is the same as.)

Preferable specific examples of the cyanine compound according to the present invention represented by the general formula (VI) include the following compound Nos. 37-No. 48. In the following examples, the anion is omitted from the cation. In the cyanine compound according to the present invention, the polymethine chain may have a resonance structure, and the cation may be on a nitrogen atom in the other heterocyclic skeleton.

Preferable specific examples of the cyanine compound according to the present invention represented by the general formula (VII) include the following compound No. 49-No. 56.

  Preferable specific examples of the cyanine compound according to the present invention represented by the general formula (VIII) include the following compound No. 57-No. 64.

  In the optical filter of the present invention, the amounts of the cyanine compound represented by the above general formula (I) and the cyanine compounds represented by the above general formulas (VI) to (VIII) are the above general formulas (VI) to (VIII). The cyanine compound represented by the above general formula (I) is preferably used in an amount of 0.001 to 2.0 mol, more preferably 0.01 to 1.0 mol, per 1.0 mol of the cyanine compound represented by Is preferable because the fluorescence of the cyanine compounds represented by the general formulas (VI) to (VIII) is quenched.

In the optical filter of the present invention, the total content of the cyanine compound represented by the general formula (I) and the compound having a maximum absorption at 550 to 620 nm used as necessary is usually 0.1 to 1000 mg / m. ² , preferably 5 to 100 mg / m ² . When the content is less than 0.1 mg / m ² , the light absorption effect cannot be sufficiently exhibited. When the content exceeds 1000 mg / m ² , the color of the filter becomes too strong, and the display quality, etc. In addition, there is a possibility that the lightness may decrease due to an increase in the blending amount of the light absorber.

The optical filter of the present invention contains at least one cyanine compound represented by the above general formula (I). Each of the cyanine compounds has an absorption maximum wavelength in the range of 300 to 1100 nm or in the vicinity thereof, and can selectively absorb and block some ultraviolet rays, visible rays, or near infrared rays. The optical filter of the present invention to be contained is particularly suitable as an optical filter for an image display device used for improving the quality of a display image. The optical filter of the present invention is for an image display device such as a liquid crystal display device (LCD), a plasma display panel (PDP), an electroluminescence display (ELD), a cathode tube display device (CRT), a fluorescent display tube, and a field emission display. In addition, it can be used for various applications such as spectacle lenses, windows, analyzer applications, semiconductor device applications, astronomical observation applications, and optical communication applications.

The optical filter of the present invention is usually disposed in front of the display. For example, the optical filter of the present invention may be directly attached to the surface of the display. When a front plate is provided in front of the display, the optical filter is attached to the front side (outside) or the back side (display side) of the front plate. May be.

Although the shape of the optical filter of the present invention is not particularly limited, each layer such as an undercoat layer, an antireflection layer, a hard coat layer, a lubricating layer, and a protective layer is usually provided on the transparent support as necessary. What was provided is mentioned. Examples of the method of incorporating the optional components of the cyanine compound according to the present invention, a light absorber that is a dye compound other than the cyanine compound according to the present invention, and various stabilizers into the optical filter of the present invention include (1) Transparent support A body or any layer, (2) a transparent support or any layer coating method, and (3) any two adjacent pressure-sensitive adhesive layers selected from the transparent support and any layer (4) A method of providing a light-absorbing layer containing a light-absorbing agent such as a cyanine compound according to the present invention separately from any arbitrary layer.

Examples of the material for the transparent support include inorganic materials such as glass; cellulose esters such as diacetylcellulose, triacetylcellulose (TAC), propionylcellulose, butyrylcellulose, acetylpropionylcellulose, and nitrocellulose; polyamides; polycarbonates; polyethylenes Polyester such as terephthalate, polyethylene naphthalate, polybutylene terephthalate, poly-1,4-cyclohexanedimethylene terephthalate, polyethylene-1,2-diphenoxyethane-4,4-dicarboxylate, polybutylene terephthalate; polystyrene; polyethylene, Polyolefin such as polypropylene and polymethylpentene; Acrylic resin such as polymethyl methacrylate; Polycarbonate; Polysulfone Polyether sulfone; polyether ketone; polyetherimides; polyoxyethylene, and polymer materials such as norbornene resins. The transmittance of the transparent support is preferably 80% or more, and more preferably 86% or more. The haze is preferably 2% or less, and more preferably 1% or less. The refractive index is preferably 1.45 to 1.70.

In the transparent support, other light absorbers other than the cyanine compound according to the present invention, infrared absorbers, ultraviolet absorbers, fluorescent quenchers, phenol-based, phosphorus-based, sulfur-based antioxidants, flame retardants , Lubricants, antistatic agents, inorganic fine particles, light resistance-imparting agents, aromatic nitroso compounds, aminium compounds, iminium compounds, transition metal chelate compounds, and the like. Processing can also be performed.

  As the light absorber other than the cyanine compound according to the present invention, for example, when an optical filter is used for an image display device, the light absorber for adjusting the color tone, the light absorption for preventing reflection of external light and reflection. In the case where the image display device is a plasma display, a light absorber for preventing infrared remote control malfunction is used.

As the light absorber for color tone adjustment, trimethine indolium compound, trimethine benzoxazolium compound, trimethine benzothiazolium compound are used for removing orange light having a wavelength of 450 to 620 nm. Trimethine cyanine derivatives such as pentamethine oxazolium compounds, pentamethine cyanine derivatives such as pentamethine thiazolium compounds, squarylium dye derivatives, azomethine dye derivatives, xanthene dye derivatives, azo dye derivatives, oxonol dye derivatives, benzylidene dye derivatives A pyromethene dye derivative; an azo metal complex derivative: a rhodamine dye derivative; a phthalocyanine derivative; a porphyrin derivative; a dipyrromethene metal chelate compound.

As a light absorber for preventing reflection of external light and reflection (corresponding to a wavelength of 480 to 500 nm), a trimethine indolium compound, a trimethine oxazolium compound, a trimethine thiazolium compound, an indolidene trimethine thiazonium Trimethine cyanine derivatives such as compounds; phthalocyanine derivatives; naphthalocyanine derivatives; porphyrin derivatives; dipyrromethene metal chelate compounds.

As a light absorber for preventing infrared remote control malfunction (corresponding to a wavelength of 750 to 1100 nm), a diimonium compound; a pentamethine benzoindolium compound, a pentamethine benzoxazolium compound, a pentamethine benzothiazolium compound, etc. Pentamethine cyanine derivatives; heptamethine indolium compounds, heptamethine benzoindolium compounds, heptamethine oxazolium compounds, heptamethine benzoxazolium compounds, heptamethine thiazolium compounds, heptamethine benzothiazolium compounds, etc. Methinecyanine derivatives; squarylium derivatives; nickel complexes such as bis (stilbenedithiolato) compounds, bis (benzenedithiolato) nickel compounds, bis (camphagethiolato) nickel compounds; Conductor; azo dye derivatives; phthalocyanine derivatives; porphyrin derivatives; dipyrromethene metal chelate compounds, and the like.

In the optical filter of the present invention, the above light absorber for color tone adjustment, a light absorber for preventing reflection of external light and reflection, and a light absorber for preventing infrared remote control malfunction (near infrared absorber) are: The layer containing the cyanine compound according to the present invention may be contained in the same layer or may be contained in another layer. Each of which usage is usually in the range of per unit area 0.1 to 1000 mg / ^{m 2} of the optical filter, preferably 5 to 100 mg / ^{m 2.}
Examples of the inorganic fine particles that can be added to the transparent support include silicon dioxide, titanium dioxide, 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. Treatment, mixed acid treatment, ozone oxidation treatment and the like.
The said undercoat which can be provided in the optical filter of this invention is a layer used between a transparent support body and an optical filter layer, when providing the filter layer containing a light absorber separately from arbitrary each 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 filter layer side, or a layer containing a polymer having affinity with the polymer of the filter layer. In addition, the undercoat layer is provided on the surface of the transparent support on which the filter layer is not provided, and improves the adhesion between the transparent support and a layer (for example, an antireflection layer or a hard coat layer) provided thereon. It may be provided for improving the affinity between the optical filter and the adhesive for bonding the optical filter and the image display device. The thickness of the undercoat layer is preferably 2 nm to 20 μm, more preferably 5 nm to 5 μm, further preferably 20 nm to 2 μm, still more preferably 50 nm to 1 μm, and most preferably 80 nm to 300 nm. The undercoat layer containing a polymer having a glass transition temperature of −60 to 60 ° C. adheres the transparent support and the filter layer due to the tackiness of the polymer. Polymers having a glass transition temperature of −60 to 60 ° C. are exemplified by polymerization of vinyl chloride, vinylidene chloride, vinyl acetate, butadiene, neoprene, styrene, chloroprene, acrylic ester, methacrylic ester, acrylonitrile or methyl vinyl ether, or a copolymer thereof. It can be obtained by polymerization. The glass transition temperature is preferably 50 ° C. or lower, more preferably 40 ° C. or lower, further preferably 30 ° C. or lower, further preferably 25 ° C. or lower, and further preferably 20 ° C. or lower. Most preferred. The elastic modulus at 25 ° C. of the undercoat layer is preferably 1 to 1000 MPa, more preferably 5 to 800 MPa, and most preferably 10 to 500 MPa. The undercoat layer whose surface is a rough surface forms a filter layer on the rough surface, thereby bonding the transparent support and the filter layer. An undercoat layer having a rough filter layer surface can be easily formed by applying a polymer latex. The average particle size of the latex is preferably 0.02 to 3 μm, and more preferably 0.05 to 1 μm. Examples of the polymer having an affinity for the binder polymer of the filter layer include acrylic resins, cellulose derivatives, alginic acid, gelatin, casein, starch, polyvinyl alcohol, polyvinyl butyral, polyvinyl pyrrolidone, soluble nylon, and polymer latex. The optical filter of the present invention may be provided with two or more undercoat layers. In the undercoat layer, a solvent for swelling the transparent support, a matting agent, a surfactant, an antistatic agent, a coating aid, a hardening agent, and the like may be added.

In the antireflection layer that can be provided in the optical filter of the present invention, a low refractive index layer is essential. The refractive index of the low refractive index layer is lower than the refractive index of the transparent support. The refractive index of the low refractive index layer is preferably 1.20 to 1.55, and more preferably 1.30 to 1.50. The thickness of the low refractive index layer is preferably 50 to 400 nm, and more preferably 50 to 200 nm. The low refractive index layer is a layer made of a fluorine-containing polymer having a low refractive index (Japanese Patent Laid-Open Nos. 57-34526, 3-130103, 6-115023, 8-313702, and 7- 168004), a layer obtained by a sol-gel method (described in JP-A-5-208811, JP-A-6-299091, and JP-A-7-168003), or a layer containing fine particles (Japanese Patent Publication No. 60). -59250, JP-A-5-13021, JP-A-6-56478, JP-A-7-92306, and JP-A-9-288201). In the layer containing fine particles, voids can be formed in the low refractive index layer as microvoids between the fine particles or within the fine particles. The layer containing fine particles preferably has a porosity of 3 to 50% by volume, and more preferably has a porosity of 5 to 35% by volume.

In order to prevent reflection in a wide wavelength region, in the antireflection layer, in addition to the low refractive index layer, a layer having a high refractive index (medium / high refractive index layer) is preferably laminated. The refractive index of the high refractive index layer is preferably 1.65 to 2.40, and more preferably 1.70 to 2.20. The refractive index of the middle refractive index layer is adjusted to be an 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 1.50 to 1.90, and more preferably 1.55 to 1.70. The thickness of the middle / high refractive index layer is preferably 5 nm to 100 μm, more preferably 10 nm to 10 μm, and most preferably 30 nm to 1 μm. The haze of the middle / high refractive index layer is preferably 5% or less, more preferably 3% or less, and most preferably 1% or less. The middle / 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, styrene copolymer, styrene-butadiene copolymer, polyvinyl chloride, polycarbonate, polyamide, melamine resin, phenol resin, epoxy resin, cyclic (alicyclic or aromatic) isocyanate and polyol. And the like obtained by the reaction. Polymers having other cyclic (aromatic, heterocyclic, alicyclic) groups and polymers having a halogen atom other than fluorine as a substituent also have a high refractive index. You may use the polymer formed by the polymerization reaction of the monomer which introduce | transduced the double bond and enabled radical hardening.

In order to obtain a higher refractive index, inorganic fine particles may be dispersed in the polymer binder. The refractive index of the inorganic fine particles is preferably 1.80 to 2.80. The inorganic fine particles are preferably formed from metal oxides or sulfides. Examples of the metal oxide or sulfide include titanium oxide (for example, rutile, rutile / anatase mixed crystal, anatase, amorphous structure), tin oxide, indium oxide, zinc oxide, zirconium oxide, and zinc sulfide. Among these, titanium oxide, tin oxide, and indium oxide are particularly preferable. The inorganic fine particles are mainly composed of oxides or sulfides of these metals, and can further contain other elements. The main component means a component having the largest content (mass%) 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 that is film-forming and can be dispersed in a solvent, or is itself a liquid, such as alkoxides of various elements, salts of organic acids, coordination compounds bonded to coordination compounds (eg chelate compounds), active inorganics A medium / high refractive index layer can also be formed using a polymer.

An antiglare function (function of preventing incident scenery from being transferred to the film surface by scattering incident light on the surface) can be imparted to the surface of the antireflection layer. For example, it has an anti-glare function by forming fine irregularities on the surface of the transparent film and forming an antireflection layer on the surface, or by forming irregularities on the surface with an embossing roll after forming the antireflection layer. An antireflection layer can be obtained. An antireflection layer having an antiglare function generally has a haze of 3 to 30%.

The said hard-coat layer which can be provided in the optical filter of this invention has hardness higher than the hardness of the said transparent support body. The hard coat layer preferably contains a crosslinked polymer. The hard coat layer can be formed using an acrylic, urethane, or epoxy polymer, oligomer, or monomer (for example, an ultraviolet curable resin). A hard coat layer can also be formed from a silica-based material.

A lubricating layer may be formed on the surface of the antireflection layer (low refractive index layer). The lubricating layer has a function of imparting slipperiness to the surface of the low refractive index layer and improving scratch resistance. The lubricating layer can be formed using polyorganosiloxane (for example, silicon oil), natural wax, petroleum wax, higher fatty acid metal salt, fluorine-based lubricant or derivative thereof. The thickness of the lubricating layer is preferably 2 to 20 nm.

When the cyanine compound according to the present invention is contained in an optical filter, the above-mentioned “(3) Method for containing in an adhesive layer between any two adjacent members selected from a transparent support and any layer” is adopted. For example, after the cyanine compound or the like according to the present invention is contained in the pressure-sensitive adhesive, the above-described transparent support and any two adjacent layers may be bonded using the pressure-sensitive adhesive. As the pressure-sensitive adhesive, known transparent adhesives for laminated glass such as silicone-based, urethane-based, acrylic-based pressure-sensitive adhesives, polyvinyl butyral adhesives, ethylene-vinyl acetate-based adhesives, and the like can be used. Moreover, when using this adhesive, as needed, crosslinking agents, such as a metal chelate type, an isocyanate type, and an epoxy type, can be used as a hardening | curing agent. Moreover, it is preferable that the thickness of an adhesive layer shall be 2-400 micrometers.

  When employing the above-mentioned “(4) Method for providing a light absorbing layer containing a light absorber such as a cyanine compound according to the present invention separately from each optional layer”, the cyanine compound according to the present invention is used as it is. A light absorption layer can be formed, or a light absorption layer can be formed by dispersing in a binder. Examples of the binder include natural polymer materials such as gelatin, casein, starch, cellulose derivatives, and alginic acid, or polymethyl methacrylate, polyvinyl butyral, polyvinyl pyrrolidone, polyvinyl alcohol, polyvinyl chloride, styrene-butadiene copolymer, polystyrene, Synthetic polymer materials such as polycarbonate and polyamide are used.

When the binder is used, an organic solvent can be used at the same time. The organic solvent is not particularly limited, and various known solvents can be used as appropriate. For example, alcohols such as isopropanol Ether ethers such as methyl cellosolve, ethyl cellosolve, butyl cellosolve, butyl diglycol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, diacetone alcohol, esters such as ethyl acetate, butyl acetate, methoxyethyl acetate; Acrylic esters such as ethyl acrylate and butyl acrylate; fluorinated alcohols such as 2,2,3,3-tetrafluoropropanol; hydrocarbons such as hexane, benzene, toluene and xylene; methylene dichloride, dichloroe Emissions, chlorinated hydrocarbons such as chloroform and the like. These organic solvents can be used alone or in combination.

In the production of the optical filter of the present invention, the concentration of the coating liquid containing the cyanine compound, the organic solvent and other various additives according to the present invention is 1 to 5% by mass, particularly 2 to 3% by mass. preferable.

The undercoat layer, the antireflection layer, the hard coat layer, the lubricating layer, the filter layer, etc. are general. The undercoat layer, the antireflection layer, the hard coat layer, the lubricating layer, the filter layer, etc. are general. It can be formed by a coating method. As a coating method, a dip coating method, an air knife coating method, a curtain coating method, a roller coating method, a wire bar coating method, a gravure coating method, an extrusion coating method using a hopper (described in US Pat. No. 2,681,294), etc. Is mentioned. Two or more layers may be formed by simultaneous application. Regarding the simultaneous application method, US Pat. No. 2,761,789, US Pat. No. 2,941,898, US Pat. No. 3,508,947, US Pat. No. 3,526,528 and Yuji Harasaki “Coating Engineering”, page 253 (published by Asakura Shoten in 1973) There is a description.

Hereinafter, the present invention will be described in more detail with evaluation examples, examples and comparative examples. However, the present invention is not limited by the following examples.
Evaluation Example 1 shows the fluorescence quenching ability evaluation of the cyanine compound according to the present invention, and Evaluation Example 2 shows a comparison of the ε values of the cyanine compound and the comparative compound according to the present invention.
Moreover, Examples 1-6 show the preparation examples of the optical filter containing the cyanine compound which concerns on this invention, and the comparative example 1 shows the preparation examples of the optical filter containing a comparison compound.

[Evaluation Example 1] Fluorescence quenching ability evaluation compound No. 4 and no. No. 12 perchlorate, compound no. The fluorescence quenching ability for 37 perchlorates was evaluated. Evaluation is performed by preparing a coating solution by mixing 2.5 g of Sumipex LG (acrylic binder manufactured by Sumitomo Chemical Co., Ltd., resin content: 40% by mass), 2.5 g of methyl ethyl ketone, and a cyanine compound with the composition of [Table 1]. The coating solution was applied to a close-treated 188 μm thick polyethylene terephthalate film with a bar coater # 20, and then dried at 100 ° C. for 10 minutes to prepare a test piece. A fluorescence spectrum of the test piece was measured, and a compound no. The fluorescence intensity of the test solution was determined when the fluorescence intensity at 37 at λmax = 600 nm was 1.0, and the fluorescence quenching ability was evaluated. The results are shown in [Table 1].

[Evaluation Example 2] Comparative compound No. 4, no. 16 and no. No. 28 perchlorate and comparative compound No. For 1, the ε value was measured and compared. The results are shown in [Table 2].

[Example 1] Preparation of optical filter 1
A coating liquid was prepared with the following composition, and the coating liquid was applied to a 188 μm-thick polyethylene terephthalate film subjected to easy adhesion treatment with a bar coater # 20, and then dried at 100 ° C. for 10 minutes. An optical filter having a film layer with a thickness of 10 μm (cyanine compound content of 2.0 mg / m ² ) was obtained. With respect to this optical filter, when the absorption spectrum was measured with an ultraviolet-visible near-infrared spectrophotometer V-570 manufactured by JASCO Corporation, λmax was 671 nm and the half width was 50 nm.

(Combination)
Sumipex LG 2.5g
(Acrylic resin binder manufactured by Sumitomo Chemical Co., Ltd., 40% by mass of resin)
Compound No. 4 perchlorate 2mg
Methyl ethyl ketone 2.5g

[Example 2] Preparation of optical filter 2
Compound No. Compound No. 4 instead of the perchlorate of No. 4 An optical filter was prepared in the same manner as in Example 1 except that 16 perchlorate was used, and the absorption spectrum of the obtained optical filter was measured with an ultraviolet-visible near-infrared spectrophotometer V-570 manufactured by JASCO Corporation. As a result of measurement, λmax was 764 nm and the half width was 50 nm.

[Example 3] Preparation of optical filter 3
Compound No. Compound No. 4 instead of the perchlorate of No. 4 An optical filter (cyanine compound content of 2.0 mg / m ² ) was prepared in the same manner as in Example 1 except that 28 perchlorate was used, and the obtained optical filter was UV-visible by JASCO Corporation. When the absorption spectrum was measured with a near-infrared spectrophotometer V-570, λmax was 450 nm and the half-value width was 50 nm.

[Example 4] Preparation of optical filter 4
A pressure-sensitive adhesive solution was prepared by the following composition, and the pressure-sensitive adhesive solution was applied to a 188 μm-thick polyethylene terephthalate film subjected to easy adhesion treatment with a bar coater # 90, and then dried at 100 ° C. for 10 minutes. An optical filter (cyanine compound content 2.0 mg / m ² ) having an adhesive layer having a thickness of about 10 μm on the film was obtained. The optical filter was measured with an ultraviolet-visible near-infrared spectrophotometer V-570 manufactured by JASCO Corporation. As a result, λmax was 671.5 nm and the half-value width was 50 nm.

(Combination)
Compound No. 4 perchlorate 2.0mg
Acrylic adhesive (DB Bond 5541: Diabond) 20g
80g of methyl ethyl ketone

[Example 5] Preparation of optical filter 5
The following formulation was melt kneaded with a plastmill at 260 ° C. for 5 minutes. After kneading, a dye-containing pellet was obtained from a nozzle having a diameter of 6 mm using an extrusion water cooling pelletizer. The pellets were formed into a thin plate (cyanine compound content 2.0 mg / m ² ) having a thickness of 0.25 mm at 250 ° C. using an electric press. When the absorption spectrum of this thin plate was measured with an ultraviolet-visible near-infrared spectrophotometer V-570 manufactured by JASCO Corporation, λmax was 672 m and the half-value width was 50 nm.

(Combination)
Iupilon S-3000 100g
(Mitsubishi Gas Chemical Company; polycarbonate resin)
Compound No. 4g perchlorate 0.01g

[Example 6] Preparation of optical filter 6
A UV varnish was prepared by the following composition, and the UV varnish was applied to a 188 μm thick polyethylene terephthalate film subjected to easy adhesion treatment by a bar coater # 9, followed by drying at 80 ° C. for 30 seconds. Thereafter, an optical filter (cyanine compound content of 2.0 mg / m ² ) having a filter layer with a cured film thickness of about 5 μm was obtained by irradiating 100 mJ of ultraviolet rays with a high-pressure mercury lamp with an infrared cut film filter. With respect to this optical filter, an absorption spectrum was measured with an ultraviolet-visible near-infrared spectrophotometer V-570 manufactured by JASCO Corporation. As a result, λmax was 671.5 nm and the half width was 50 nm.

(Combination)
Adekaoptomer KRX-571-65 100g
(UV cured resin made by ADEKA, resin content 80% by mass)
Compound No. 4 perchlorate 0.5g
Methyl ethyl ketone 60g

[Comparative Example 1] Preparation of optical filter 7
Compound No. 4 instead of the perchlorate of No. 4 An optical filter was prepared in the same manner as in Example 1 except that 1 was used, and the absorption spectrum of the obtained optical filter was measured with an ultraviolet-visible near-infrared spectrophotometer V-570 manufactured by JASCO Corporation. Was 689 nm and the half width was 70 nm.

From the results of Evaluation Example 1 shown in [Table 1], when the cyanine compound represented by the general formula (I) is used, the fluorescence intensity of the cyanine compound represented by the general formula (VI) becomes weak. It turns out to be extinguished. Moreover, from the result of Evaluation Example 2, the cyanine compound represented by the general formula (I) had a high ε value, but the ε value of the comparative compound was low. Further, as apparent from Examples 1 to 6, the optical filter containing the cyanine compound represented by the general formula (I) has sharp light absorption in the wavelength region of 300 to 1100 nm, and the image Although it is suitable as an optical filter for a display device, an optical filter containing a comparative compound has a wide half-value width and is not suitable as an optical filter for image display.

Claims (11)

An optical filter comprising at least one cyanine compound represented by the following general formula (I):

(Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁶ are each independently an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or the number of carbon atoms. 7 to 30 arylalkyl groups or a substituent represented by the following general formula (II), R ³ and R ⁴ , and R ⁵ and R ⁶ may be bonded to each other to form a ring structure. , R ²¹ , R ²² and R ²³ are each independently a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group, a diphenylamino group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or Represents an arylalkyl group having 7 to 30 carbon atoms, and the alkyl group or the alkylene portion of the arylalkyl group is -O-, -S-, -CO-, -COO-, -OCO-, -CH = CH- , -NHCO- or -CONH- May also ^be, among of R ^{21, R 22} and ^{R 23,} the substituent adjacent optionally form a ring structure together .n is 0,2 or 3, ^{An q-} Represents a q-valent anion, q is 1 or 2, and p represents a coefficient for maintaining a neutral charge.)

(Wherein R ^{a to} R ⁱ each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the methylene group in the alkyl group is substituted with —O— or —CO—). Z ¹ represents a direct bond or an alkylene group having 1 to 8 carbon atoms, and the methylene group in the alkylene group is -O-, -S-, -CO-, -COO-, -OCO. —, —SO ₂ —, —NH—, —CONH—, —NHCO—, —N═CH— or —CH═CH— may be substituted, and M is Fe, Co, Ni, Ti, Cu. , Zn, Zr, Cr, Mo, Os, Mn, Ru, Sn, Pd, Rh, Pt or Ir.) The optical filter according to claim 1, wherein the cyanine compound represented by the general formula (I) is a cyanine compound represented by the following general formula (III).

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ²³ , An ^q− , q and p are the same as those in the general formula (I).) The optical filter according to claim 1, wherein the cyanine compound represented by the general formula (I) is a cyanine compound represented by the following general formula (IV).

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ²¹ , R ²² , R ²³ , An ^q− , q and p are the same as those in the general formula (I). , R ²¹ , R ²² and R ²³ may be different from each other, and adjacent substituents may be linked to form a ring structure.) The optical filter according to claim 1, wherein the cyanine compound represented by the general formula (I) is a cyanine compound represented by the following general formula (V).

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ²¹ , R ²² , R ²³ , An ^q− , q and p are the same as those in the general formula (I). , R ²¹ , R ²² and R ²³ may be different from each other, and adjacent substituents may be linked to form a ring structure.) An optical filter comprising at least one compound having a maximum absorption in the range of 550 to 620 nm in at least one of the cyanine compounds represented by the general formulas (I) and (III) to (V). 6. The optical filter according to claim 5, wherein the compound having the maximum absorption in the range of 550 to 620 nm is a cyanine compound represented by the following general formula (VI).

(In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ²¹ , R ²² , R ²³ , An ^q− , q and p are the same as those in the general formula (I). .) 6. The optical filter according to claim 5, wherein the compound having the maximum absorption in the range of 550 to 620 nm is a cyanine compound represented by the following general formula (VII).

Wherein R ³⁰ and R ³¹ are each independently a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, carbon Represents an arylalkyl group having 7 to 30 atoms or a substituent represented by the above general formula (II), wherein R ³² , R ³³ and R ³⁶ each independently represent a hydrogen atom or an alkyl having 1 to 10 carbon atoms; Group, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a substituent represented by the above general formula (II), wherein R ³⁴ and R ³⁵ are each independently hydrogen represents atom, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, a substituent represented by an arylalkyl group or the general formula -C 7~30 ^{(II), R 34} And R ³⁵ are bonded to each other The alkylene group of the alkyl group or arylalkyl group may be —O—, —S—, —CO—, —COO—, —OCO—, —CH═CH—, -NHCO- or -CONH- may be substituted, s and t are each independently a number of 1 to 4, and An ^q- , q and p are the same as those in the general formula (I). is there.) 6. The optical filter according to claim 5, wherein the compound having the maximum absorption in the range of 550 to 620 nm is a cyanine compound represented by the following general formula (VIII).

(In the formula, R ³⁷ represents a hydrogen atom, a hydroxyl group, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an aryl having 7 to 30 carbon atoms. Represents an alkyl group or a substituent represented by the general formula (II), and R ³⁸ and R ³⁹ each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl having 6 to 30 carbon atoms. Group, an arylalkyl group having 7 to 30 carbon atoms, a halogen atom, a nitro group, a cyano group, or a substituent represented by the above general formula (II), and the alkylene portion of the alkyl group or arylalkyl group is- O—, —S—, —CO—, —COO—, —OCO—, —CH═CH—, —NHCO— or —CONH— may be substituted, and d is a number from 1 to 4. , ^{An q-,} q and p are the General formula (I) which is the same as.) The optical filter according to claim 1, wherein the cyanine compound is contained in an amount of 0.1 to 1000 mg / m ² per unit area. The optical filter according to claim 1, which is for an image display device. The optical filter according to claim 10, wherein the image display device is a plasma display.