WO2008035533A1 - Optical filter containing squarylium dye-metal complex compound and filter for display panel using the same - Google Patents

Abstract

Disclosed is an optical filer having excellent weather resistance, which enables good color reproducibility regardless of emission wavelength change in a light-emitting device due to use environment a color image display, in particular temperature change in the color image display. Also disclosed is a filter for display panels using such an optical filter. The optical filter is characterized by containing a squarylium dye-metal complex compound, which has a maximum absorption in the visible region while containing a partial structure represented by the general formula (1) below, and a binder. [chemical formula 1] (1) (In the formula, M represents a metal atom; A represents an organic group; B represents a five-membered ring; X represents an oxygen atom, a nitrogen atom or a sulfur atom; Y represents a nitrogen atom when n = 0, or represents a carbon atom when n = 1; R represents a substituent; n represents 0 or 1; and m represents an integer of 0-3.)

Description

 Specification

 Optical filter containing squarylium dye monometallic complex compound and display panel filter using the same

 The present invention relates to an optical filter containing a squarylium dye metal complex compound and a display panel filter using the same. More specifically, the present invention relates to an optical filter characterized by containing a specific squarylium dye metal complex compound and a filter for a display panel using the same, and in particular, effectively shields neon emission emitted from plasma display panel force. This is a display panel filter that can be used.

 Background art

 Conventionally, various types of image display devices using a cathode tube, a fluorescent display tube, a field emission, a plasma panel, a liquid crystal, an electoluminescence, etc. have been developed as color image display devices. In particular, in recent years, plasma display panels have been used as display panels for various types of electronic devices such as large-sized wall-mounted televisions, and the demand for them has increased, and the number of such displays will continue to increase.

 [0003] These color image display devices basically take the form of displaying an image using a combination of light emission of three primary colors of red, green and blue. In particular, in plasma displays, xenon and neon mixed gas is excited by discharge to emit vacuum ultraviolet light, and light emission of three primary colors is obtained by using light emission of red, blue, and green phosphors by excitation of the vacuum ultraviolet light. . In the plasma display, after neon atoms are excited, so-called neon orange light centered around 600 nm is emitted when returning to the ground state (see, for example, Non-Patent Document 1). For this reason, the plasma display has a drawback that the orange color is mixed with the red color and it is impossible to obtain a strong red color! /.

In general, a color image display device absorbs light emission other than the three primary colors using a so-called bandpass filter to obtain a clear color image and correct the color balance of the image. Yes. [0005] As the band-pass filter, there are various investigations on the use of a dye. In this case, there is no absorption other than the intended absorption, and the weather resistance such as heat resistance and light resistance of the dye. However, there is also a problem that the color reproducibility of the color image changes due to the use environment of the color image display device itself, especially the change in the emission wavelength of the light emitting device due to the temperature change. It is necessary to consider carefully.

 On the other hand, a squarylium dye-metal complex compound (metal-squarylium compound mixed composition) in which a metal and a specific squarylium compound are mixed is known.

 [0007] For example, a structural force S of a squarylium dye metal complex compound represented by the following structure A is disclosed (see Patent Document 1).

 [0008] [Chemical 1-1] Structure A

Furthermore, squarylium dye metal complex compounds represented by the following structures B 1 and B 2 are disclosed (for example, see Patent Document 2).

[0010] [Chemical 1-2]

— 1

Further, a squarylium dye metal complex compound represented by the following structure c, an infrared absorber, and a display panel filter are disclosed (for example, see Patent Document 3).

[0012] [Chemical 1-3] Construction

(Wherein X and X ′ represent a group having active hydrogen, Y and Y are a hydrogen atom, alkyl

 1 2

 Represents an amino group, and k and k ′ each represent an integer of !!-4. )

However, in this publication, only the squarylium compound represented by the following structure D is specifically disclosed as the squarylium compound corresponding to the structure C, and the infrared absorber and the infrared cut-off are also used in the usage form. It only describes the display filter. [0014] [Chemical 1-4] Structure D

[In the formula, Z to Z represent a hydrogen atom or an alkyl group.]

 1 6

 Regarding the squarylium metal compounds of Patent Documents 1 to 3 described above, no description as an optical filter can be seen! /.

[0016] Examples of using the squarylium dye as an optical filter include a color filter using a specific squarylium dye (see, for example, Patent Document 4), and further substitution of the squarylium dye on the benzene ring. Pyrazole-based squarylium dyes that contain only OH groups as groups are described (see, for example, Patent Document 5), but these are sufficient to cut neon orange light or other unwanted light. Further improvement is demanded for the high light resistance even under high-temperature and high-humidity environmental conditions, due to changes in the emission wavelength of the light-emitting device due to changes in the operating environment temperature. It was hoped that the deterioration of the color reproducibility of the color image would be improved.

 [0017] In view of the above situation, an optical filter capable of obtaining a clear color image even when the light emission wavelength of the light-emitting device changes due to a change in the use environment temperature as well as further improving the weather resistance of the compound, and the The display panel filter used is desired.

 Patent Document 1: International Publication No. 02 / 50190A1 Pamphlet

 Patent Document 2: Pamphlet of International Publication No. 04 / 7447A1

 Patent Document 3: Japanese Unexamined Patent Publication No. 2000-159776

Patent Document 4: Japanese Patent Laid-Open No. 2000-345059 Patent Document 5: Japanese Patent Laid-Open No. 2005-197240

 Non-Patent Literature 1: Journal of the Institute of Image Information and Television Engineers, Vol. 51, No. 4, P. 459-463 (1997) Disclosure of the Invention

 Problems to be solved by the invention

[0018] The present invention provides an optical filter containing a squalium dye-metal complex compound that can be suitably used in a color image display device such as a plasma display, and a display panel filter using the optical filter. Objective. Furthermore, an optical filter that has excellent weather resistance and enables good color reproducibility regardless of the use environment of the display device itself for high power images, in particular, the emission wavelength of the light emitting device due to temperature change, and the use of the same. The object is to provide a filter for a display panel. In particular, it can effectively cut neon light emission, has excellent weather resistance, and can achieve good color reproducibility regardless of the use environment of the color image display device itself, especially the light emission wavelength change of the light emission device due to temperature changes. An object of the present invention is to provide a filter for a plasma display panel.

 Means for solving the problem

[0019] The above object of the present invention is achieved by the following configurations.

 [0020] 1. An optical filter comprising a squalium dye-metal complex compound having a maximum structure in the visible light region and having a partial structure represented by the following general formula (1) and a binder.

 [0021] [Chemical formula 1] General formula (1)

(In the formula, M represents a metal atom, A represents an organic group, B represents a 5-membered ring, X represents an oxygen atom, a nitrogen atom or a sulfur atom, and Y represents a nitrogen atom when n = 0. , Char if n = l Represents a primary atom, R represents a substituent, n represents 0 or 1, and m represents an integer of 0 to 3. )

2. The optical filter as described in 1 above, wherein in the general formula (1), A is an aryl group, a heterocyclic group or the following general formula (1 A).

 [0023] [Chemical formula 2] General formula (1 -A)

 A = C—

 Ri

(In the formula, A ¹ represents a 5-membered ring or a 6-membered ring, and R ¹ represents a hydrogen atom or a substituent.)

 3. The optical finolator according to 1 or 2, wherein in the general formula (1), the metal atom M is any one of copper, nickel, cobalt, zinc, aluminum, and beryllium.

 [0025] 4. A display panel filter using the optical filter according to any one of 1 to 3 above.

 The invention's effect

 [0026] According to the present invention, it is possible to provide an optical filter containing a squarylium dye metal complex compound that can be suitably used for a color image display device such as a plasma display, and a display panel filter using the optical filter. Furthermore, an optical filter that has excellent weather resistance and enables good color reproducibility regardless of the use environment of the color image display device itself, in particular, the emission wavelength change of the light emitting device due to temperature change, and a display using the same Panel filters can be provided. In particular, it can effectively cut neon light emission, has excellent weather resistance, and enables good color reproducibility regardless of the usage environment of the color image display device itself, especially the light emission wavelength change of the light emission device due to temperature change. A filter for a plasma display panel can be provided.

 BEST MODE FOR CARRYING OUT THE INVENTION

[0027] As a result of intensive studies in view of the above problems, the present inventors have found that an optical filter containing a specific squarylium dye metal complex compound and a binder, and a filter for a display panel using the optical filter are described above. See that the goal is achieved. I put it out.

 That is, the gist of the present invention is an optical filter containing a squarylium dye metal complex compound having a partial structure represented by the general formula (1) and a binder, and a display comprising the same The present invention relates to a panel filter and a plasma display panel filter.

 [0029] Hereinafter, the present invention will be described in detail.

 [0030] A squarylium dye metal complex compound having a partial structure represented by the general formula (1) according to the present invention contained in the optical filter of the present invention (hereinafter referred to as the compound of the present invention or the squarylium dye metal complex compound of the present invention) (Also called).

 [0031] If the compound of the present invention has absorption in the visible light region (400 to 700 nm) in a solution state and does not substantially absorb in the near-infrared region, the compound of the present invention does not have the display of the present invention. Can be suitably used for an optical filter. It is preferred that the compound of the present invention has an absorption maximum in the visible light region in the solution state. Further, the compound of the present invention preferably has an absorption maximum in the range of 450 to 650 nm. It has an absorption maximum at 570 to 610 nm in the solution state! /, The power S most preferred! /.

 Next, the squarylium dye-metal complex compound having a partial structure represented by the general formula (1) will be described.

 In the general formula (1), M represents a metal atom, and the metal is particularly limited as long as it can form a chelate and form the compound of the present invention represented by the general formula (1). There is no. For example, copper, nickel, cobalt, zinc, aluminum, beryllium, iron, silver, chromium, mangan, iridium, vanadium, titanium, ruthenium, molybdenum, tin, bismuth, osmium, magnesium, calcium, strontium, barium, gallium , Germanium, platinum, gold, mercury, etc. In terms of chelating ability, copper, nickel, cobalt, zinc, anoleminium, beryllium, iron, silver, chromium, manganese, titanium, ruthenium, osmium, magnesium, calcium, norlium, gallium, mercury Most preferred are copper, nickel, cobalt, zinc, anoleminium, and beryllium.

[0034] B represents a 5-membered ring. In the general formula (1), B is an important partial structure for visible light absorption characteristics and complex formation with metals. The five-membered ring represented by B includes a squaric acid residue and If it is possible to form a ring together with the carbon atom and Y that are bonded, there is no particular limitation on the constituent atoms forming the ring, but the constituent atoms are arbitrarily selected from carbon, nitrogen, and sulfur atoms. Examples of preferred combinations of atoms include furan, pyrrole, thiophene, pyrazole, imidazole, triazole, thiadiazole, oxazole, thiazole, benzothiazole, benzo Xazole ring, benzoselenazole ring, benzotelrazole ring, benzimidazole ring, thiazoline ring, indolenine ring, oxadiazole ring, pyrazolone ring, isoxazolone ring, pyrrolidone ring, thoxathiazolone ring, pyrrolopyrrole ring, pyrroloimidazole ring , Pyrrolotriazole ring, virazolopyrrole ring, pyrazoloimi Examples include a dazole ring, a pyrazolotriazole ring, a pyrazo mouth pyrimidine ring, an imidazolopyrazole ring, an isoxazolidine ring, a thiximidazolidine ring, an imidazolidine ring, an imidazolidinethione ring, and a thiazolidinone ring. These may have a substituent at any position. In the present invention, specific examples of soot that are particularly preferable in terms of complex formation with a metal include a structure represented by the following general formula lb— ;! to lb-11.

[Chemical 3]

1b— 1 1b-2 1b— 3 1b— 4

5>

 1b— 6 1b-: 1b— 8

1b— 9 1b— 10 1b— 11

[0036] In the formula lb— ;! to lb— 11, * represents the bonding position of B in the general formula (1) to the squarylium structure, and Q represents C (Ra), C = 〇, C = S, C = N— Ra, N (Ra), 0, S, S = 〇, S (= O), Se, Te, preferably C = 〇, C = S, N (Ra), 0, S More preferably, N (Ra), 0, and S.

 [0037] Xb represents an oxygen atom or a sulfur atom, preferably a sulfur atom, and T and T are NR

 1 2 a, C (Ra), C = 〇, C = S, 0, S, Z represents O or S, O is preferred, Rd represents a substituent, and L to L are N = or C (Ra) = is represented.

 13

 [0038] b represents an integer of 0 to 2, c represents 0 or 1, and Ra represents a hydrogen atom or a substituent.

[0039] The substituent represented by Ra is not particularly limited. For example, an alkyl group (for example, a methylol group, an ethyl group, a propyl group, an isopropyl group, a tertbutyl group, a pentyl group, a hexyl group, an octyl group) Group, dodecyl group, trifluoromethyl group, etc.), cycloalkyl group (for example, cyclopentyl group, cyclohexyl group, etc.), aryl group (for example, phenyl group, naphthinole group, etc.), isylamino group (for example, acetylylamino group, Benzoylamino group, etc.), alkyl Thio group (eg, methylthio group, ethylthio group, etc.), arylthio group (eg, phenylthio group, naphthylthio group, etc.), alkenyl group (eg, butyl group, 2-propenyl group, 3-butyr group, 1-methyl group) 3-propenyl group, 3-pentyl group, 1-methyl-3-buturyl group, 4 monohexenyl group, cyclohexenyl group, etc.), halogen atom (eg fluorine atom, chlorine atom, bromine atom, iodine atom, etc.), Alkynyl groups (for example, propargyl group), heterocyclic groups (for example, pyridyl group, thiazolyl group, oxazolyl group, imidazolinol group, etc.), alkylsulfonyl groups (for example, methylsulfonyl group, ethylsulfonyl group, etc.), A reelsulfonyl group (for example, a phenylsulfonyl group, a naphthylsulfonyl group, etc.), an alkylsulfier group (for example, Tilsulfyl group, etc.), arylsulfyl group (for example, phenylsulfiel group, etc.), phosphono group, isyl group (for example, acetyl group, bivaloyl group, benzoyl group, etc.), strong rubamoyl group (for example, sulfamoyl group). Minocarbonyl group, methylaminocarbonyl group, dimethylaminocarbonyl group, butylaminocarbonyl group, cyclohexylaminocarbonyl group, phenylaminocarbonyl group, 2-pyridylamino force sulfonyl group, etc.), sulfamoyl group (for example, , Aminosulfonyl group, methylaminosulfonyl group, dimethylaminosulfonyl group, butylaminosulfonyl group, hexylaminosulfonyl group, cyclohexylaminosulfonyl group, octylaminosulfonyl group, dodecylaminominorephoninore group, Enylaminosulfonyl group, naphth Ruaminosulfonyl group, 2-pyridylaminosulfonyl group, etc.), sulfonamide group (eg, methanesulfonamide group, benzenesulfonamide group, etc.), cyano group, alkoxy group (eg, methoxy group, ethoxy group, propoxy group) ), Aryloxy groups (for example, phenoxy groups, naphthyloxy groups, etc.), heterocyclic oxy groups, siloxy groups, acyloxy groups (for example, acetyloxy groups, benzoyloxy groups, etc.), sulfonic acid groups, sulfonic acid salts, aminocarbonyls An oxy group, an amino group (for example, an amino group, an ethylamino group, a dimethylamino group, a butylamino group, a cyclopentylamino group, a 2-ethylhexyloleamino group, a dodecinoleamino group, etc.), an anilino group (for example, a phenylamino group, a chlorophenyl group) , Toluidino group, Anishi Group, naphthylamino group, 2-pyridinoreamino group, etc., imide group, ureido group (for example, methylureido group, ethylureido group, pentylureido group, cyclohexylureido group, octylureido group, dodecylureido group, phenylenoureido group) , Naphthinoreureido group, 2-pyridinoreaminoureido group, etc.) Alkoxycarbonylamino groups (for example, methoxycarbonylamino groups, phenoxy group carbonylamino groups, etc.), alkoxycarbonyl groups (for example, methoxycarbonyl groups, ethoxycarbonyl groups, phenoxycarbonyl, etc.), aryloxycarbonyls, etc. Examples thereof include groups such as a group (for example, phenoxycarbonyl group), a heterocyclic thio group, a thioureido group, a carboxyl group, a carboxylic acid salt, a hydroxyl group, a mercapto group, and a nitro group. These substituents may be further substituted with the same substituent. Preferably, it is an alkyl group, an alkenyl group, a cyano group, or an alkoxy group, and when a plurality of Ras are present, each Ra may be the same or different in each formula. If necessary, a fused ring in which Ras are arbitrarily bonded to each other is actively introduced, and the color tone of the squarylium dye metal complex compound having the partial structure represented by the general formula (1) is adjusted. It is also possible to adjust to a desired color tone. In this case, examples of the condensed ring include the above-described aryl group and heterocyclic group, and the condensed ring is further substituted with the same group as the substituent represented by Ra described above! / Moyore.

[0040] The substituent represented by Rd is not particularly limited, and examples thereof include a group having the same meaning as the substituent represented by Ra described above. In the general formula lb-8, when a plurality of Rd are present, each Rd may be the same or different. Rd may be arbitrarily bonded to form a ring.

 [0041] Specific examples of B that are particularly preferable in terms of the stability of the metal complex include lb-2, lb-3, 1b-5, and lb-11, and have a wide range of visible light absorption characteristics. Specific examples of B preferable for having an absorption maximum at 450 to 650 nm include a structure represented by the general formulas lb— ;! to lb—3, lb—7 to lb 11. In particular, since it has a maximum absorption at 570 to 610 nm, preferred examples include the general formulas lb— ;! to lb—3, lb—7, lb—10, and lb 11.

 In the general formula (1), X represents an oxygen atom or a sulfur atom, preferably an oxygen atom. Y represents a nitrogen atom when n = 0, and a carbon atom when n = l.

 [0043] R represents a substituent, and m represents an integer of 0 to 3. Although there is no restriction | limiting in particular as this substituent, For example, the group synonymous with the substituent represented by Ra mentioned above can be mentioned.

[0044] When m is 1 or more, R may be bonded to any position on ring B to form a ring. Alternatively, in the case of 3, a plurality of Rs may be the same or different. Rs may be bonded together at any position to form a ring.

 [0045] A represents an organic group, and examples of the organic group include the same groups as the substituents represented by Ra described above, preferably an aryl group, a heterocyclic group, or an alkenyl group. May be substituted with the same group as the substituent represented by Ra. From the viewpoint of fastness of the squarylium dye monometallic complex compound represented by the general formula (1), A is more preferably an aryl group, a heterocyclic group, or a substituent represented by the general formula (1 A).

In the general formula (1 A), A ¹ represents a 5-membered ring or a 6-membered ring, and the 5-membered ring represented by A ¹ includes a virazolidinedione ring, an isoxazolone ring, a pyrazolone ring, a pyrrolidone Rings (eg, 1H—PyrroylLu 2 (5H) —one ring), thoxathiazolidinone rings (eg, rhodanine ring, ₄ thixamidazolidine on ring, 5 thixamidazolidin 2—on ring) Pyrrolotriazole ring (for example, 7,7a dihydro-1H pyrox [1, 2-b] [l, 2,4] triazole ring, 7,7a dihydro-1H pyrox [2, 1-c] [l, 2, 4] triazole ring), pyrazolotriazole ring (for example, 7, 7a dihydro-1H pyrazo mouth [5, 1-c] [1, 2, 4] triazo, mono-recycle, 7, 7a dihydro-1H Pyrazo, mouth [1, 5 b] [l, 2, 4] triazole ring), pyrazo mouth pyrimidine ring, imidazole ring (eg 4H-imida Ring), imidazolopyrazole ring, pyrrole ring, isoxazolidinedione ring, thixamidazolidinone ring (for example, 4 thiximidazolidine 2-one ring), imidazolidinedione ring (for example, hydantoin) Ring), imidazolidine dithione ring (for example, imidazolidine 2, 4 dithione ring), thiazolidine dione ring, pyrazole dione ring, indole ring, etc., which are represented by Ra described above at an arbitrary position. You may have a group synonymous with a substituent.

[0047] The 6-membered ring represented by A ^1, for example, Kisajen rings cyclohexane (1, 3 hexa Gen rings cyclohexane, 1, 4 Kisajen ring to Shikuro), dihydropyridine ring (1, 4-dihydropyridine ring, 3,4-dihydropyrazine ring), 4H-pyran ring, 4H-thiopyran ring, pyridone ring (eg pyridine-2 (3H) -one ring), pyridinethione ring (eg pyridine-2 (3H) — Thione ring), pyridinedione ring (for example, pyridine-2, 4 (3H, 5H) -dione ring), barbituric acid ring, thiobarbituric acid ring, oxazine ring, thiazine ring, dihydropyrimidine dione ring (for example, Dihydropyrimidine 1, 4, 6 (1H, 5H) —dione ring), dihydropyrimidine Dithione rings (eg, dihydropyrimidine—4,6 (1H, 5H) —dithione ring), oxazine dione rings (eg, 4H 1, 3-oxazine 4,6 (5H) —dione ring), oxadiazine rings (eg, 4H—1, 2, 3 oxaziazine ring), etc., and these have a group having the same meaning as the substituent represented by Ra described above at any position, and may be V.

[0048] R ¹ represents a hydrogen atom or a substituent, and the substituent is the same group as the substituent represented by Ra described above. R ¹ is preferably a hydrogen atom, an alkyl group or a halogen atom, more preferably a hydrogen atom or an alkyl group, still more preferably a hydrogen atom, a methyl group or an ethyl group, and most preferably a hydrogen atom. .

 [0049] The squarylium dye metal complex compound having a partial structure represented by the general formula (1) of the present invention has a plurality of squarylium dyes arranged on one metal ion in order to neutralize the charge. You may rank. In the case where there are a plurality of coordinated squarylium dyes, only the squarylium dye having the same structure or the squarylium dyes having different structures may be used.

 [0050] The squarylium dye metal complex compound having a partial structure represented by the general formula (1) of the present invention may have a counter ion when a counter ion is required to neutralize the charge. . For example, whether the squarylium dye-metal complex compound having the partial structure represented by the general formula (1) of the present invention has a cation, an anion force, or a net ionic charge depends on the metal. , The number of coordinated squarylium dyes, and the substituents. When a substituent has a dissociable group, it may dissociate and have a negative charge. Typical cations are inorganic or organic ammonium ions (eg, tetraalkyl ammonium ions, pyridinium ions), alkali metal ions and protons, while anions are specifically inorganic. It can be either an anion or an organic anion, for example, a halogen anion (eg fluoride ion, chloride ion, bromide ion, iodide ion)

), Substituted aryl sulfonate ions (eg, p toluene sulfonate ion, p black benzene sulfonate ion), aryl disulfonate ions (eg, 1,3-benzene disulfonate ion, 1, 5 naphthalene disulfonate ion) 2, 6 naphthalene sulphonate ion), alkyl sulfate ion (eg methyl sulfate ion), sulfate ion, thiocyanate ion, perchlorate ion, tetrafluoroborate ion, hexafluorophosphine Examples thereof include ate ion, picrate ion, acetate ion, trifluoromethanesulfonate ion, and the like.

 [0051] Specific examples of squarylium dye metal complex compounds having a partial structure represented by the general formula (1) of the present invention will be given below. However, the present invention is not limited to these. It should be noted that the structural formula shown here is only one limit structure among the resonance structures that can be taken. For convenience, a covalent bond (indicated by one) and a coordination bond (indicated by...) Are distinguished. It does not represent a distinction.

[0052] [Chemical 4]

a0053 Ġ

[0054] [Chemical 6]

[0055] [Chemical 7]

ss∞990 ^

[0057] [Chemical 9]

[0058] [Chemical 10]

[0059] [Chemical 11]

[0060] [Chemical 12]

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[0069] [Chemical 21]

[0070] [Chemical 22]

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[0072] [Chemical 24]

[0073] [Chemical 25]

[0074] [Chemical 26]

[0075] [Chemical 27]

[0076] [Chemical 28]

[0077] [Chemical 29]

[0078] [Chemical 30]

[0079] [Chemical 31]

[0080] [Chemical 32]

[0081] [Chemical 33]

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[0084] [Chemical 36]

[0085] [Chemical 37]

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[0089] [Chemical 41]

[0090] [Chemical 42]

[0091] [Chemical 43]

[0092] [Chemical 44]

[0093] [Chemical 45]

[0094] [Chem 46]

Hereinafter, a general method for producing a squarylium dye metal complex compound having a partial structure represented by the general formula (1) will be described.

[0096] These compounds can be synthesized with reference to conventionally known methods. For example, JP-A-6-250357, JP-A-7-175187, JP-A-3-82255, JP-A-3-261539, JP-A-4-13834, JP-A-63-210167, JP-A-10-36695, JP-A-2000- 25 Refer to gazettes such as 1958, 2000-285978, 2000-345059, International Publication Nos. 01/044233, 02/050190, 04/007447, etc. Power S can be. Specific examples of the synthesis method are shown below, but other compounds can be synthesized in the same manner, and the synthesis method is not limited thereto.

 [0097] << Synthesis of Exemplified Compound 1 >>

 (Synthesis of squarylium dye A)

 It was synthesized according to the following scheme.

 [0098] [Chemical 47]

[0099] 4 (4 Butyl (ethyl) aminophenyl) -3 Hydroxy-3 Cyclobutene 1,2 —Dione 5.4 g n-butanol monoole 110 ml, toluene 110 ml and 3 ethyl 2,4 dimethylbilol 2.7 g were added for 4 hours. After heating to reflux, the solvent was distilled off under reduced pressure. 20 ml of methanol was added to the residue, and the precipitate was collected by filtration to obtain 3.6 g of compound A (squarium dye A). MASS, 1H—NMR, IR spectrum confirmed the target intermediate.

 [0100] (Synthesis of Exemplified Compound 1)

A mixture of Compound A (3.6 g), zinc acetate dihydrate (1 lg) and ethanol (500 ml) was heated to reflux for 6 hours, and the precipitate was collected by filtration to give 3.3 g of Exemplified Compound (1). It was confirmed as the target product by elemental analysis. Exemplified Compound 1 was a reddish purple solution in black mouth form, and the maximum absorption wavelength was 554 nm. [0101] << Synthesis of Exemplified Compound 3 >>

 In the synthesis of Exemplified Compound 1, 4- (4 butyl (ethyl) aminophenyl) 3 -hydroxysilane 1 cyclobutene 1,2 dione is converted to 4- (4- (jetylamino) 2 methylphenyl) -3 hydroxy-3 cyclobutene 1, Exemplified compound 3 was obtained in the same manner except that the diacetic acid was changed to 2 dione and the zinc acetate dihydrate was changed to nickel acetate dihydrate. Exemplified Compound 3 is a reddish purple solution in black mouth form and has a maximum absorption wavelength of 560 ηm.

[0102] << Synthesis of Exemplified Compound 24 >>

 (Synthesis of squarylium dye D)

 It was synthesized according to the following scheme.

[0103] [Chemical 48]

Compound B 9.0 g, n-butanol 90 ml, toluene 45 ml and compound C 9. Og were calored and treated at 110 ° C. for 5 hours. Thereafter, 100 ml of methanol was added and reacted at 80 ° C. for 1 hour, and then the precipitate was collected by filtration to obtain 8.2 g of Compound D. It was confirmed by MASS, 1H—NMR and IR spectrum to be the desired intermediate.

 [0105] (Synthesis of Exemplified Compound 24)

Except for changing the zinc acetate dihydrate to nickel acetate dihydrate in the synthesis of Exemplified Compound 1, 7.6 g of Exemplified Compound 24 was obtained in the same manner. Elemental analysis confirmed the target product. Exemplified Compound 24 is a blue-purple to blue solution in chloroform, acetone, acetonitrile, and THF, and absorbs in the range of 585 to 610 nm in these solvents. It was confirmed that there was a maximum of convergence.

<Synthesis of Exemplified Compound 25>

 (Synthesis of squarylium dye G)

 It was synthesized according to the following scheme.

[0107] [Chemical 49]

[0108] In the synthesis of Exemplified Compound 24, squarylium dye G was obtained by the same procedure except that Compound B was changed to Compound E and Compound C was changed to Compound F. MASS, 1H—NMR, IR spectrum confirmed the target intermediate.

 [Synthesis of Exemplified Compound 25]

 The obtained squarylium dye G 6. Og was dissolved in 300 ml of methanol and an aqueous solution in which 5.3 g of Ni (PF) was dissolved in 100 ml of water was added and stirred at room temperature for 5 hours. Concentrate solvent gradually

6 2

 The precipitate was collected by filtration and washed with water and methanol to obtain 7.2 g of Exemplified Compound 25. The target product was confirmed by elemental analysis. Exemplified Compound 25 was a red-purple to blue-purple solution in chloroform, acetone, acetonitrile, and THF, and it was confirmed that these solvents had an absorption maximum in the range of 560 to 590 nm.

[0110] << Synthesis of Exemplified Compound 42 >>

 (Synthesis of squarylium dye J)

 It was synthesized according to the following scheme.

[0111] [Chemical 50]

 H J

[0112] In the synthesis of Exemplary Compound 1, squarylium dye J was synthesized in the same manner as the synthesis of squarylium dye A. It was confirmed by MASS, 1H-NMR and IR spectra that it was the desired intermediate.

[0113] (Synthesis of Exemplified Compound 42)

 Using the obtained squarylium dye J, Exemplified Compound 42 was obtained in the same manner as in the synthesis of Exemplified Compound 25. Exemplified Compound 42 was a reddish purple to blue-violet solution in chloroform, acetone, acetonitrile, THF, and DMF, and it was confirmed that these solvents had an absorption maximum in the range of 555 to 590 nm.

[0114] << Synthesis of Exemplified Compound 52 >>

 (Synthesis of squarylium dye M)

 It was synthesized according to the following scheme.

[0115] [Chemical 51]

In the synthesis of Exemplified Compound 24, the squarylium dye M was synthesized in the same manner as the synthesis of squarylium dye D. MASS, 1H—Intermediate of interest by NMR and IR spectra I confirmed.

 [0117] (Synthesis of Exemplified Compound 52)

 The obtained squarylium dye M and aluminum (tris) ethylacetoacetate were reacted in an ethyl acetate-acetic acid mixed solvent at 50 ° C. for 2 hours to obtain Exemplified Compound 52. Elemental analysis confirmed the target product. It was confirmed that Exemplified Compound 52 was a blue-violet solution in black mouth form and had an absorption maximum at 586 nm.

 [0118] << Synthesis of Exemplified Compound 122 >>

 Squaric acid 0.5 g, 1-phenol 3-tert-butylpyrazolone 2. lg, toluene 10 ml, n-butanol 5 ml were placed in a sealed container and reacted at 180 ° C. for 10 minutes while irradiating with microwaves. The resulting solid was collected by filtration and washed with a small amount of methanol. MASS, 1H—NMR, IR spectrum confirmed the target intermediate.

 [0119] After this solid lg was dissolved in 300 ml of methanol, 0.29 g of nickel (Π) acetylacetonate dihydrate was added and stirred at room temperature for 3 hours. After evaporating the solvent under reduced pressure, 10 ml of acetonitrile was added to the residue and recrystallized to obtain Exemplified Compound 122. Elemental analysis confirmed the target product. Exemplified Compound 122 was a red-purple solution in acetone and confirmed to have an absorption maximum at 535 nm.

 [0120] << Synthesis of Exemplified Compound 140 >>

 (Synthesis of squarylium dye R)

 It was synthesized according to the following scheme.

[0121] [Chemical 52]

[0122] 50 ml of butanol and 4 · Og of triethylenomine were stirred and dissolved at 60 ° C in the intermediate N 5 · 4 g. Next, a solution of 4.6 g of intermediate O in 20 ml of 1-butanol was added dropwise over 1 hour. After completion of the dropwise addition, the mixture is stirred for 2 hours at the same temperature, concentrated, dissolved in 200 ml of ethyl acetate and separated, neutralized, washed with water and concentrated. The concentrate was purified by column chromatography. Next, the concentrate was dissolved in 200 ml of acetone, 70 ml of 2M-HC1 was added, and the mixture was heated to reflux for 6 hours. The reaction solution was concentrated at about 100 m, dropped into 300 ml of water and the precipitated crystals were filtered to obtain 6.2 g of intermediate P.

 [0123] Intermediate P 3 · lg, Intermediate Q 3. 2g with 1-butanol and 40ml

 Heated to reflux for 8 hours. The reaction solution was cooled, and the precipitated crystals were filtered to obtain 5.3 g of squarylium dye R. It was identified by MASS, 1H-NMR and IR spectra and confirmed to be the target product.

 [0124] (Synthesis of Exemplified Compound 140)

Exemplified compound 140 was obtained in the same manner as in the synthesis of Exemplified compound 1. Exemplified compound 140 0 was blue-violet in ethyl acetate. [0125] << Synthesis of Exemplified Compound 142 >>

 100 ml of methanol was added to 2.3 g of squarylium dye R and 0.34 g of copper chloride dihydrate obtained in the synthesis of Exemplified Compound 140, and the mixture was heated to reflux for 2 hours. The reaction solution was cooled to room temperature, and the precipitated crystals were filtered to obtain 1.8 g of Exemplified Compound 142. It was identified by elemental analysis and confirmed to be the target product. Exemplified Compound 142 was reddish purple in ethyl acetate

Yes

 <Synthesis of Exemplified Compound 143>

 Exemplified Compound 143 was obtained in the same manner as in Exemplified Compound 142 except that copper chloride was changed to magnesium chloride.

[0127] <Synthesis of Exemplified Compound 248>

 (Synthesis of squarylium dye U)

 It was synthesized according to the following scheme.

[0128] [Chemical 53]

 U

[0129] Add 1-butanol 40ml and Tonolen 40ml to intermediate S 3 · lg and intermediate T 1 · 9g

 Heated to reflux for 8 hours. The reaction solution was cooled, and the precipitated crystals were filtered to obtain squarylium dye U 4.lg. It was identified by MASS, 1H-NMR and IR spectra and confirmed to be the target product.

[0130] (Synthesis of Exemplified Compound 248) A mixture of the obtained squarylium dye U lg, beryllium sulfate tetrahydrate 0.2 g, ethanol 100 ml and water 30 ml was heated to reflux for 5 hours, and the precipitate was collected by filtration to obtain 0.8 g of Exemplified Compound 248. It was. It was identified by elemental analysis and confirmed to be the target product. Exemplified Compound 248 was reddish purple in black mouth form.

 [0131] << Synthesis of Exemplified Compound 257 >>

 In the synthesis of Exemplified Compound 122, Exemplified Compound 257 was obtained in the same manner as in the synthesis of Exemplified Compound 122, except that nickel (Π) acetylacetate dihydrate was changed to copper chloride dihydrate. It was confirmed that Exemplified Compound 257 showed a red color in acetone and had an absorption maximum at 512 nm.

 [0132] << Synthesis of Exemplified Compound 258 >>

 Exemplified Compound 258 was obtained in the same manner as in Exemplified Compound 257 except that copper chloride dihydrate was changed to zinc acetate dihydrate. Exemplified Compound 258 was red in acetone and confirmed to have an absorption maximum at 536 nm.

 [0133] Optical filter

 Next, the optical filter will be described.

 [0134] The optical filter of the present invention contains the squarylium dye metal complex compound of the present invention alone or in combination, and can be used in a form that absorbs visible light. The optical filter of the present invention is preferably used for the purpose of improving color reproducibility, such as color correction, and in particular, used for the purpose of improving color reproducibility by absorbing transmitted light. Is preferred.

 [0135] (Binder)

 The optical filter of the present invention further contains a binder together with the compound of the present invention. Examples of the type of binder include aliphatic ester resins, acrylic resins, melamine resins, urethane resins, aromatic ester resins, polycarbonate resins, aliphatic polyolefin resins, aromatic polyolefin resins, polybulu resins, polybulu alcohols. Examples thereof include resins, polyvinyl modified resins (PVB, EVA, etc.), and copolymer resins thereof. The amount of the binder used is 10 to 500 times by mass, preferably 50 to 350 times by mass with respect to the total mass of the compound of the present invention.

[0136] (Production of optical filter) In producing the optical filter of the present invention, a solvent may be used for mixing the binder and the compound of the present invention. Examples of the solvent include halogen-based, alcohol-based, ketone-based, ester-based, aliphatic hydrocarbon-based, aromatic hydrocarbon-based, ether-based solvents, and mixtures thereof. The concentration of the composition varies depending on the gram extinction coefficient, the thickness of the coating, the target absorption intensity, the target visible light transmittance, and the like. In addition, the solution or dispersion of the compound of the present invention and the binder resin includes, as necessary, a polybutyral resin, a polyurethane resin, a phenol resin, a phenoxy resin, a petroleum resin, and a rosin resin. A dispersing agent such as

 [0137] The optical filter of the present invention has generally known additives such as phenol-based and phosphorus-based antioxidants, halogen-based and phosphoric acid-based flame retardants, heat-resistant anti-aging agents, and ultraviolet absorbers. Further, a lubricant, an antistatic agent and the like can be blended.

 [0138] When a plurality of compounds of the present invention are contained, each compound is separately mixed in a binder resin, and each binder resin containing the compound of the present invention is laminated, so that each compound is in a separate layer. It may take the form of an existing laminate. In this case, the number of stacking operations increases, which is not preferable from the viewpoint of manufacturing, but it is not preferable, but it is possible to select a more preferable binder resin according to the compound, which is useful when subtle color adjustment is required. It is.

 [0139] As a method for producing the laminate, for example,

 (1) A method in which the compound of the present invention and a binder resin are made into a solution or dispersion of an appropriate solvent, applied onto a sheet-like or film-like transparent substrate by a known application method, and dried.

 (2) According to a conventional molding method for thermoplastic resins, the compound of the present invention and a binder resin are melt-kneaded and molded into a film or sheet by extrusion molding, injection molding, compression molding, etc., and the film Alternatively, a method of adhering the sheet to the transparent substrate with an adhesive or the like,

(3) A method in which the compound of the present invention and a binder resin are melt-kneaded and extruded into a film or sheet, and extrusion laminated on a transparent substrate, (4) a method of melt-kneading the compound of the present invention and a binder resin and coextruding with a transparent resin substrate,

 The above-mentioned method (1) is particularly preferable among them.

[0140] As a method for producing the latter single-layer sheet or film, for example,

 (1) A method in which the compound of the present invention and a binder resin are cast on a carrier as a solution or dispersion of an appropriate solvent and dried.

 (2) According to a conventional molding method for thermoplastic resins, the compound of the present invention and a binder resin are melt-kneaded and molded into a film or sheet by extrusion molding, injection molding, compression molding, etc.,

 Take the power S, etc.

[0141] (Dispersant)

 The optical filter of the present invention may use a dispersant together with the compound of the present invention. Examples of the dispersant used as necessary include polybutyral resin, phenoxy resin, rosin-modified phenol resin, petroleum resin, cured rosin, rosin ester, maleated resin, polyurethane resin and the like. The amount to be used is 0.5 to 150 times, preferably 10 to 100 times the total mass of the compound of the present invention.

[0142] The filter according to the present invention contains the compound of the present invention alone or as a mixture. As its inclusion form, typically, a laminate in which the compound-containing resin layer of the present invention is formed on a sheet-like or film-like transparent substrate with a binder resin containing the compound of the present invention, or And a single layer sheet or film of the compound-containing resin of the present invention comprising the binder resin itself containing the compound of the present invention.

 [0143] Filter for display panel

 The filter for a display panel of the present invention is disposed in front of a self-luminous display device such as a plasma display or an organic EL display, and is used for color correction or blocking light in an unnecessary wavelength range.

[0144] Examples of the substrate include a transparent resin plate, a transparent film, and transparent glass.

There is no particular limitation as long as the light transmittance of OOnm is 40% or more. For example, Polly Mido, polysulfone (PSF), polyethersulfone (PES), polyethylene terephthalate (PET), polymethylene methacrylate (PMMA), polycarbonate (PC), polyetherol ether ketone (PEEK), polypropylene (PP) , Triacetyl cellulose (TAC) and the like S. In particular, acrylic resins such as polyethylene terephthalate (PET), triacetyl cellulose (TAC), and polymethyl methacrylate (PMMA), polycarbonate resins, and the like are preferably used.

 [0145] The thickness of the substrate is not particularly limited as long as it has a certain degree of mechanical strength. However, it is usually 20 mm, 10 mm, 20 mm, 20 mm, preferably 1 mm, and 20 mm. 200〃 m force is especially preferred! / ヽ.

 [0146] The method for producing the display panel filter of the present invention using the compound of the present invention is not particularly limited.

 (1) A method for inclusion in a transparent adhesive,

 (2) a method of incorporating a polymer molded body,

 (3) A method of coating a polymer molded body or glass surface,

 Etc.

[0147] Specific examples of the transparent adhesives listed in (1) include acrylic adhesives, silicone adhesives, urethane adhesives, polybutyl petital adhesives (PVB), and ethylene vinyl acetate. Sheet-like or liquid adhesives such as polybule ethers, saturated amorphous polyesters, melamine resins, etc., among them acrylic adhesives, urethane adhesives, polybulupetite, etc. Lar pressure-sensitive adhesives are preferred. The addition amount is usually 1 0Ppm～30 mass _^0/0, 10Ppm～20 mass _^0/0 force S Preferably, lOppm~; 10 mass _^0/0 is preferred especially.

 [0148] As a method of containing the polymer resin molded article listed in (2),

 (A) a method of kneading a pigment mixture into a resin and heat-molding;

 (B) A method in which a resin or resin monomer and a pigment mixture are dispersed and dissolved in an organic solvent, and a polymer molded body is prepared by a casting method.

[0149] The resin used in (A) is preferably as transparent as possible when a plate or film is produced. Specifically, polyethylene terephthalate (PET), polyether sulfone (PES), polyethylene Naphthalate, polyarylate, polyetherketone, poly Polycarbonate such as carbonate, polyethylene, polypropylene and nylon 6, cellulose resin such as polyimide and triacetyl cellulose, fluorine-based resin such as polyurethane and polytetrafluoroethylene, butyl compounds such as polychlorinated butyl, polyacrylic acid, poly Addition polymer of acrylic acid ester, polyacrylonitrile, butyl compound, polymethacrylic acid, polymethacrylic acid ester, vinylidene chloride such as polyvinylidene chloride, vinylidene fluoride / trifluoroethylene copolymer, ethylene / butyl acetate copolymer, etc. Or a copolymer of a fluorinated compound, a polyether such as polyethylene oxide, an epoxy resin, a polybutyl alcohol, or a polybutyl butyral.

 [0150] As processing conditions, the compound of the present invention is added to a base polymer powder or pellet, mixed, heated and dissolved at 150 to 350 ° C, and then molded to form a plate, or pressed. A method of forming a film with an extruder, a raw material with an extruder, and a method of forming a film with a thickness of 10 to 200 111 by stretching 1 to 2 axes 2 to 5 times at 30 to 120 ° C Is mentioned. When mixing, additives such as plasticity used for normal resin molding may be added.

 [0151] In the casting method of (B), a mixture containing the compound of the present invention is added to and dissolved in an organic solvent solution or an organic solvent of a resin or resin monomer, and if necessary, a plasticizer, a polymerization initiator, an oxidation A plate or film can be produced by adding an inhibitor, pouring onto a mold or drum having the required surface state, solvent volatilization, drying or polymerization, solvent volatilization and drying.

 [0152] The resins used include aliphatic ester resins, acrylic resins, melamine resins, urethane resins, aromatic ester resins, polycarbonate resins, aliphatic polyolefin resins, aromatic polyolefin resins, polybule resins, poly Examples thereof include resin monomers of bulle alcohol resins, polymodified resins (PVA, EVA, etc.) or copolymer resins thereof. Examples of the solvent include halogen-based, alcohol-based, ketone-based, ester-based, aliphatic hydrocarbon-based, aromatic hydrocarbon-based, ether-based solvents, and mixtures thereof.

[0153] Examples of the method for coating the polymer molded body or glass surface mentioned in (3) include a method in which the compound of the present invention is dissolved in a binder resin and an organic solvent to form a composition, and then a coating is used. Finely pulverize the compound of the present invention into a colored acrylic emulsion paint (50 (~ 500nm) is dispersed to make an acrylic emulsion water-based paint. Additives such as antioxidants that are used in ordinary paints may be added to the paint.

 [0154] Examples of the noinder include aliphatic ester resins, acrylic resins, melamine resins, urethane resins, aromatic ester resins, polycarbonate resins, aliphatic polyolefin resins, aromatic polyolefin resins, polybule resins, polyresins. Examples thereof include a bull alcohol resin, a polyvinyl modified resin (PVB, EVA, etc.) or a copolymer resin thereof.

 [0155] Examples of the solvent include halogen-based, alcohol-based, ketone-based, ester-based, aliphatic hydrocarbon-based, aromatic hydrocarbon-based, ether-based solvents, or mixtures thereof.

[0156] The concentration of the composition varies depending on the Gram extinction coefficient, coating thickness, target absorption intensity, target visible light transmittance, etc., and is usually 0.1 ppm to 30 mass relative to the mass of the binder resin. %. The resin concentration is usually from !! to 50 mass% with respect to the entire paint.

 [0157] The paint produced by the above method is formed by forming a thin film on a substrate by a known method such as a bar coder, blade coater, spin coater, reno coater, die coater, or spray coating method. Can apply, coating power S.

 [0158] The display panel filter of the present invention preferably has an electromagnetic wave shielding function or a near-infrared shielding function. As an electromagnetic wave shield, a laminate using a silver thin film or a metal mesh mainly using copper can be used. As a laminate using a silver thin film, a laminate in which a dielectric such as indium oxide, zinc oxide, and titanium oxide and silver are alternately laminated is preferable. As the metal mesh, a fiber mesh obtained by vapor-depositing metal on a fiber, an etching mesh that forms a pattern by using a technique of photolithography, and obtains a mesh by etching can be used. In addition, a method of performing a battering with an ink containing a metal, a method of applying silver halide, developing and fixing, etc. are also suitably used.

[0159] As for the near-infrared shielding function, when an electromagnetic wave shield using a silver thin film is used, the near-infrared radiation can be simultaneously blocked due to scattering of silver by free electrons. That In addition, when mesh, ink patterning or development is used, a film that absorbs or reflects near infrared rays is used separately. Various known infrared absorbers may be added to an appropriate layer.

Furthermore, a functional transparent layer such as a known antireflection layer, antiglare layer, hard coat layer, antistatic layer, or antifouling layer can be added to the display panel filter of the present invention.

 [0161] In order to obtain an electronic display or plasma display panel display device using the display panel filter of the present invention, any known display device or commercially available display device can be used without particular limitation. Can do.

 [0162] A plasma display panel display device is a device that displays a color image according to the following principle. A display electrode pair is provided between the front glass plate and the rear glass plate, and cells corresponding to each pixel (R (red), G (green), B (blue)) provided between the two glass plates are provided. Xenon gas or neon gas is sealed in the cell, and a phosphor corresponding to each pixel is applied to the back glass plate side in the cell. Due to the discharge between the display electrodes, xenon gas and neon gas in the cell are excited and emitted, and ultraviolet rays are generated. By irradiating the ultraviolet rays with the ultraviolet rays, visible light corresponding to each pixel is generated. An address electrode is provided on the rear glass plate, and a signal is applied to the address electrode to control which discharge cell is displayed and display a color image.

 Example

 [0163] Hereinafter, the present invention will be specifically described with reference to Examples, but the present invention is not limited thereto. In addition, although the display of "%" is used in an Example, unless otherwise indicated, "mass%" is represented.

[0164] Example 1 (Optical filter)

 << Production of optical filter >>

 (Production of optical filter 101)

 A 1.0% tetrahydrofuran solution of Exemplified Compound 1 and a 20% dimethoxyethane solution of polyester resin (Byron 200; manufactured by Toyobo Co., Ltd.) are mixed in a ratio of 2: 8 as a pigment. Optical filter 101 was produced by coating and drying in one turret.

[0165] (Optical fino letter; 102-; production of 105) Optical filters 102 to 105 were prepared in the same manner as in the preparation of the optical filter 101 except that Exemplified Compound 1 (pigment) was changed as shown in Table 1.

[0166] (Production of optical filter 106)

 A 0.5% dimethoxyethane solution of Exemplified Compound 1 of the present invention was prepared, and coated on a glass substrate with a bar coater and dried to produce an optical filter 106.

[0167] (Optical Fino Letter; 107-; 110)

 Optical filters 107 to 110 were prepared in the same manner as in the production of the optical filter 106 except that Exemplified Compound 1 (pigment) was changed as shown in Table 1.

[0168] <Evaluation of optical filter>

 The following evaluation was performed about the produced optical filter.

[0169] (Light resistance 1)

 Visible light is irradiated to the optical filter immediately after fabrication, and the transmittance (%) at wavelengths of 450 nm, 550 nm, 586 nm, 61 2 nm and 628 nm (TO: For example, the transmittance at 450 nm is expressed as TO (450) ) Was measured. Subsequently, after irradiating the optical filter with a xenon lamp at 70,000 lux for 5 days, similarly, visible light was irradiated, and the transmittance (%) at wavelengths of 450, 550, 586, 612 nm and 628 nm (T1) For example, the transmittance at 450 nm after the test is expressed as T1 (450)). Accumulated absolute value of transmittance change (%) at each wavelength before and after xenon lamp irradiation, and this integrated value I ΔΤ I force Light resistance was evaluated according to the following criteria

[0170] Integrated value I ΔΤ I = I TO (450) —T1 (450) | + | TO (550) —T1 (550) | + | T 0 (586) -T1 (586) | + | TO (612 ) -T1 (612) | + | TO (628) -T1 (628) |)

 a: I ΔΤ I is less than 2.5%

 b: I ΔΤ I is 2.5% to less than 5%

 c: I ΔΤ I force S5% 〜; less than 10%

 d: I ΔΤ I force sio% or more

I ΔΤ I force s indicates that the smaller the value, the more stable against xenon lamp irradiation and the better the light resistance. a and b are at a level where there is no practical problem. [0171] (Light resistance 2: Light resistance after storage at high temperature and high humidity)

 Visible light is irradiated to the optical filter immediately after fabrication, and the transmittance (%) at wavelengths of 450 nm, 550 nm, 586 nm, 61 2 nm and 628 nm (TO: For example, the transmittance at 450 nm is expressed as TO (450) ) Was measured. Subsequently, after storing the optical filter under conditions of 55 ° C and 90% RH for 3 days, the xenon lamp was further irradiated with 70,000 lux for 5 days, and then irradiated with visible light in the same manner. , 586, 612, and 628 wavelengths (%) (T1: For example, the transmittance at 450 nm after the test is expressed as T1 (450)). The absolute values of the transmittance change (%) at each wavelength before and after irradiation with the xenon lamp were integrated, and the light resistance was evaluated according to the following criteria from this integrated I ΔΤI.

[0172] Integration I ΔΤ I = I TO (450) —T1 (450) | + | TO (550) —T1 (550) | + | TO

 (586) — T1 (586) | + | TO (612) -T1 (612) | + | TO (628) -T1 (628) |) a: I ΔΤ I is less than 2.5%

 b: I ΔΤ I is 2.5% to less than 5%

 c: I ΔΤ I force S5% 〜; less than 10%

 d: I ΔΤ I force sio% or more

 The smaller I ΔΤ I force s, the more stable it is against xenon lamp irradiation, and the better the light resistance after storage under high-temperature and high-humidity conditions. a and b are at a level where there is no practical problem.

[0173] The results of the evaluation are shown in Table 1.

[0174] [Table 1] Optical filter

 Dye Binder Light resistance 1 Light resistance 2 Remarks

 No.

 1 01 1 Polyester resin a a The present invention

 102 24 Polyester trees a a Present invention

 103 50 Polyester trees a a Present invention

 104 53 Polyester lumber b b Present invention

 105 1 2 Polyester lumber a a Present invention

 106 1 None a c Comparative example

 107 24 None a c Comparative example

 108 50 None a c Comparative example

 109 53 None b d Comparative example

1 10 142 None ac Comparative example [0175] As is apparent from Table 1, it can be seen that the light resistance of the optical filter of the present invention after storage at high temperature and high humidity is improved by using a binder.

[0176] Example 2 (optical filter)

 << Production of optical filter >>

 (Production of optical filter 201A)

 A 1.0% tetrahydrofuran solution of Exemplified Compound 1 as a dye and a 20% dimethoxyethane solution of polyester resin (Byron 200; manufactured by Toyobo Co., Ltd.) as a binder are mixed at a ratio of 2: 8 to obtain a glass substrate. An optical filter 201A was prepared by applying the coating on a bar coater and drying. This filter had a reddish purple color, and even if it was a composition containing a binder, it effectively absorbed visible light.

[0177] (Production of optical filters 201B, 201C, 201D)

 In the production of optical filter 201 A, polyester resin as a binder is polychlorinated bur resin, polystyrene resin (St / HEMA / SMA = 30/40/30 copolymer, St: styrene, HEMA: 2-hydroxyethyl) Optical filters 201B, 201C, and 201D were prepared in the same manner except that the material was changed to metatalylate, SMA: stearyl metatalylate), and acrylic resin (Dianal BR-80; manufactured by Mitsubishi Rayon Co., Ltd.). All of the filters had a reddish purple color, and even if the composition was changed in the binder, it effectively absorbed visible light.

[0178] (Production of optical filter 201E)

As a pigment, a 1.0% tetrahydrofuran solution of Exemplified Compound 1 and a 20% dimethoxyethane solution of hot-melt polyester resin (trade name: SP3300X1 made by Daibond Industry Co., Ltd.) are mixed in a ratio of 2: 8 to give a release polyester film ( Made by Toyobo Co., Ltd., trade name: MRF75, thickness 75, coated with a bar coater and dried, then coated with polyester film (Toyobo Co., Ltd., trade name: A4300, thickness 100 m) with a hot roll laminator Use and peel off the polyester film for peeling, make the SP3300X1 coated side glass side, heat it with an iron with a surface of about 100 ° C for 1 minute, and paste it on a glass substrate to make an optical filter 201 E This filter had a reddish purple color, and even if it was a composition with a changed binder, it effectively absorbed visible light. [0179] (Production of optical filter 201F)

 For production of optical filter E! /, Except that hot-melt polyester resin resin as binder is changed to hot-melt ethylene acetate butyl copolymer resin (trade name: Mersen G) Thus, an optical filter 201F was produced. This filter was reddish purple, and it was found that even a composition with a changed binder effectively absorbs visible light.

 [0180] (Production of optical filters 202A to 245F)

 Optical filters 202A to 245A were prepared in the same manner except that the dye was changed as shown in Table 2 in the production of the optical filter 201A.

 [0181] The same procedure is followed, except that the optical finest letters 201B, 201C, 201D, 201E, and 201F are prepared. The procedure is the same except that the dyes are changed as shown in Tables 3, 4, 5, 6, and 7. Optical fino letters 202B to 245B, 202C to 245C, 201D to 245D, 201E to 245E, and 201F to 245FC were produced.

 [0182] All optical filters absorbed visible light effectively.

 [0183] The dyes A, B, and C used in the comparative examples are as follows.

 [0184] A: Compound described in International Publication No. 04/007447 Pamphlet Table 2 (7)

 B: The following comparative compound 1 and MS-1 were mixed in a THF solution at a ratio of comparative compound 1: MS-1 = 1: 3 (molar ratio), and the residue after evaporation of the solution under reduced pressure was used as a dye. .

 [0185] C: Exemplified compound of JP 2005-197240 A II 3

[0186] [Chemical 54]

 MS— 1

 Comparative compound 1

C

 II 1 3

[0187] << Evaluation of optical filter >>

 The following evaluation was performed about the produced optical filter.

[0188] (Light resistance)

 The light resistance of Example 1 was evaluated in the same manner as in Example 1.

[0189] (Heat resistance)

 Visible light is irradiated to the optical filter immediately after fabrication, and the transmittance (%) at each wavelength of 450 nm, 550 nm, 586 nm, 612 nm and 628 nm (TO: For example, the transmittance at 450 nm is expressed as TO (450) ) Was measured. Subsequently, the optical filter was stored at 80 ° C for 10 days, and then irradiated with visible light in the same manner, and the transmittance (%) at each wavelength of 450, 550, 586, 612, and 628 nm. (T1: For example, the transmittance at 450 nm after the test is expressed as T1 (450)). The absolute values of transmittance change (%) at each wavelength before and after storage were integrated, and this integrated I ΔΤ I force was evaluated for heat resistance according to the following criteria.

[0190] Integration I ΔΤ I = I T0 (450) —T1 (450) | + | T0 (550) —T1 (550) | + | TO

(586) — T1 (586) I + I T0 (612) -T1 (612) I + I T0 (628) -T1 (628) I a: I ΔΤ I is less than 2.5%

 b: I ΔΤ I is 2.5% to less than 5%

 c: I ΔΤ I force S5% 〜; less than 10%

 d: I ΔΤ I force sio% or more

 I ΔΤ I force The smaller the S, the more stable against heat and the better the heat resistance. a, are at a level where there is no practical problem.

[0191] (Humidity resistance)

 Visible light is irradiated to the optical filter immediately after fabrication, and the transmittance (%) at each wavelength of 450 nm, 550 nm, 586 nm, 612 nm and 628 nm (TO: For example, the transmittance at 450 nm is expressed as TO (450) ) Was measured. Subsequently, the optical filter was stored for 10 days under conditions of 50 ° C and 80% RH, and then irradiated with visible light in the same manner, and transmitted at wavelengths of 450, 550, 586, 612 nm, and 628 nm. Percentage (%) (T1: For example, the transmittance at 450 nm after the test is expressed as T1 (450)). The absolute value of the transmittance change (%) at each wavelength before and after storage was integrated, and this integrated I ΔΤ I force was evaluated for moisture resistance according to the following criteria.

[0192] Integration I ΔΤ I = I TO (450) —T1 (450) | + | TO (550) —T1 (550) | + | TO

 (586) — T1 (586) | + | TO (612) -T1 (612) | + | TO (628) -T1 (628) | a: I ΔΤ I is less than 2.5%

 b: I ΔΤ I is 2.5% to less than 5%

 c: I ΔΤ I force S5% 〜; less than 10%

 d: I ΔΤ I force sio% or more

 I ΔΤ I force The smaller the S, the more stable the humidity and the better the humidity resistance. a and b are practically acceptable levels.

[0193] The results of evaluation are shown in Tables 2-7.

[0194] [Table 2] Optical filter No. Dye Binder Light resistance Heat resistance Moisture resistance Remarks

201 A 1 Polyester resin a b a The present invention

202A 3 Polyester resin a a b The present invention

203A 5 Polyester resin a a b The present invention

204A 15 Polyester resin b b b The present invention

205A 24 Polyester lumber a a a The present invention

206A 25 Polyester resin a b a The present invention

207A 42 Polyester resin a a a The present invention

208A 52 Polyester resin a b b The present invention

209A 59 Polyester resin a b b The present invention

210A 62 Polyester resin a b b The present invention

21 1 A 71 Polyester resin a b b Present invention

Z 1 ZA 99 Polyester resin b b b The present invention

213A 100 Polyester resin b b b The present invention

214A 102 Polyester resin b b b The present invention

215A 103 Polyester resin a a a The present invention

216A 105 Polyester resin a a a The present invention

217A 122 Polyester resin a a a The present invention

218A 139 Polyester resin b b b The present invention

219A 1 0 Polyester resin a a a The present invention

220A 141 Polyester resin a a a The present invention

Z21 A 142 Polyester resin a a a The present invention

222A 143 Polyester resin a a a The present invention

223A 145 Polyester resin a a a The present invention

ZZ4A 147 Polyester resin a a a The present invention

225A 148 Polyester resin a a a The present invention

226A 158 Polyester resin b a a The present invention

Z27A 165 Polyester resin a b a The present invention

228A 169 Polyester resin a a a The present invention

Z29A 176 Polyester resin b a b The present invention

230A 192 Polyester resin b b a The present invention

231 A 193 Polyester resin a b b The present invention

232A 199 Polyester resin a a a The present invention

233A 218 Polyester resin a a b The present invention

234A 224 Polyester resin b b b The present invention

235A 230 Polyester resin b b b The present invention

236A 238 Polyester resin b b a The present invention

237A 244 Polyester resin a a a The present invention

238A 248 Polyester resin b b a The present invention

239A 251 Polyester resin b b a The present invention

240A 255 Polyester resin b b a The present invention

241 A 257 Polyester resin a a a The present invention

242A 258 Polyester resin a a a The present invention

243A A Polyester resin d d d Comparative example

244A B Polyester resin c c d Comparative example

245A C Polyester resin ddd Comparative example] Optical filter No. Dye Binder Light resistance Heat resistance Humidity resistance Remarks

201 B 1 Vinyl chloride resin a a a The present invention

202 B 3 Vinyl chloride resin a a a The present invention

203 B 5 Vinyl chloride resin a a b The present invention

204 B 15 Vinyl chloride resin b b b Present invention

205 B 24 Vinyl chloride resin a a a The present invention

206 B 25 Vinyl chloride resin a a a The present invention

207 B 42 Vinyl chloride resin a a a The present invention

208 B 52 Vinyl chloride resin a a a The present invention

209 B 59 Vinyl chloride resin a a a The present invention

210B 62 Vinyl chloride resin a a a The present invention

21 I B 71 Vinyl chloride resin a a a The present invention

212B 99 Vinyl chloride resin b a a The present invention

213B 100 Vinyl chloride resin b a a The present invention

2 MB 102 Vinyl chloride resin b b a The present invention

215B 103 Vinyl chloride resin a a a The present invention

216B 105 Vinyl chloride resin a a a The present invention

217B 1 22 Vinyl chloride resin a a a The present invention

Z 18B 139 Vinyl chloride resin a b a The present invention

219B 140 Vinyl chloride resin a a a The present invention

220B 141 Vinyl chloride resin a a a The present invention

221 B 142 Vinyl chloride resin a a a The present invention

222B 143 Vinyl chloride resin a a a The present invention

223B 145 Vinyl chloride resin a a a The present invention

224B 147 Vinyl chloride resin a a a The present invention

225B 148 Vinyl chloride resin a a a The present invention

226B 158 Vinyl chloride resin a a a The present invention

227B 165 Vinyl chloride resin a a a The present invention

228B 169 Vinyl chloride resin a a a The present invention

229B 176 Vinyl chloride resin b a a The present invention

230 B 192 Vinyl chloride resin b a a The present invention

231 B 193 Vinyl chloride resin a a a The present invention

232B 199 Vinyl chloride resin a a a The present invention

233B 218 Vinyl chloride resin a a a The present invention

234B 224 Vinyl chloride resin b b a The present invention

235B 230 Vinyl chloride resin b b b The present invention

236 B 238 Vinyl chloride resin b b a The present invention

237 B 244 Vinyl chloride resin a a a The present invention

238B 248 Vinyl chloride resin a a a The present invention

239B 251 Vinyl chloride resin a a a The present invention

240B 255 Vinyl chloride resin a a a The present invention

241 B 257 Vinyl chloride resin a a a The present invention

242B 258 Vinyl chloride resin a a a The present invention

243B A Vinyl chloride resin d d d Comparative example

244B B Vinyl chloride resin c c d Comparative example

245B C Vinyl chloride resin ddd Comparative example] Optical filter No. Dye Binder Light resistance Heat resistance Moisture resistance Remarks

201 C 1 Polystyrene resin a a a The present invention

202C 3 Polystyrene resin a a b Present invention

203C 5 Polystyrene resin a a a The present invention

204C 15 Polystyrene resin b b b Present invention

205C 24 Polystyrene resin a a a The present invention

206C 25 Polystyrene resin a a a The present invention

207C 42 Polystyrene resin a a a The present invention

208C 52 Polystyrene resin a a a The present invention

209C 59 Polystyrene resin a a a The present invention

210C 62 Polystyrene resin a a a The present invention

21 1 C 71 Polystyrene resin a a a The present invention

212C 99 Polystyrene resin a a a The present invention

213C 100 Polystyrene resin a a a The present invention

214C 102 Polystyrene resin b a b The present invention

215C 103 Polystyrene resin a a a The present invention

216C 105 Polystyrene resin a a a The present invention

217C 1 22 Polystyrene resin a a a The present invention

218C 139 Polystyrene resin a b a The present invention

219C 1 0 Polystyrene resin a a a The present invention

220C 141 Polystyrene resin a a a The present invention

221 C 142 Polystyrene resin a a a The present invention

222C 143 Polystyrene resin a a a The present invention

223C 145 Polystyrene resin a a & present invention

224C 147 Polystyrene resin a a a The present invention

225C 148 Polystyrene resin a a a The present invention

226C 158 Polystyrene resin a a a The present invention

227C 165 Polystyrene resin a a a The present invention

228C 169 Polystyrene resin a a a The present invention

229C 176 Polystyrene resin a a a The present invention

230C 192 Polystyrene resin b b a The present invention

231 C 193 Polystyrene resin a b b The present invention

232C 199 Polystyrene resin a a a The present invention

233C 218 Polystyrene resin a a b The present invention

234C 224 Polystyrene resin b b a The present invention

235C 230 Polystyrene resin b b a The present invention

236C 238 Polystyrene resin b a a The present invention

237C 244 Polystyrene resin a a a The present invention

238C 248 Polystyrene resin a a a The present invention

239C 251 Polystyrene resin a a a The present invention

240C 255 Polystyrene resin a a a The present invention

241 C 257 Polystyrene resin a a a The present invention

242C 258 Polystyrene resin a a a The present invention

243C A Polystyrene resin d d d Comparative example

244C B Polystyrene resin c c d Comparative example

245C C Polystyrene resin ddd Comparative example] Optical filter No. Dye Binder Light resistance Heat resistance Moisture resistance Remarks

201 0 1 Acrylic resin a a a The present invention

202 D 3 acrylic resin a a a The present invention

2030 5 acrylic resin a a a The present invention

204 D 15 acrylic resin b a b The present invention

2050 24 Acrylic resin a a a The present invention

2060 25 acrylic resin a b a The present invention

207 D 42 Acryl resin a a a The present invention

208 D 52 acrylic resin a a a The present invention

2090 59 acrylic resin a a a The present invention

210D 62 acrylic resin a a a The present invention

21 1 D 71 acrylic resin a a a The present invention

212D 99 acrylic resin b a a The present invention

213D 100 acrylic resin b a b The present invention

214D 102 acrylic resin b b a The present invention

215D 103 acrylic resin a a a The present invention

Z16D 105 acrylic resin a a a The present invention

217D 122 acrylic resin a a a The present invention

218D 139 acrylic resin a a a The present invention

219D 140 acrylic resin a a a The present invention

220D 141 acrylic resin a a a The present invention

221 D 142 acrylic resin a a a The present invention

222D 143 acrylic resin a a a The present invention

223 D 1 5 acrylic resin a a a The present invention

224 D 147 Acrylic resin a a a The present invention

225D 148 acrylic resin a a a The present invention

226 D 158 acrylic resin a a a The present invention

227D 165 acrylic resin a a a The present invention

228D 169 acrylic resin a a a The present invention

229D 176 Acrylic resin a a b The present invention

230D 192 acrylic resin a a a The present invention

231 D 193 acrylic resin a a b The present invention

Z32D 199 acrylic resin a a a The present invention

233D 218 acrylic resin a a a The present invention

234D 224 acrylic resin b b b The present invention

235 D 230 acrylic resin a b b The present invention

236D 238 acrylic resin b a a The present invention

237 D 244 acrylic resin a a a The present invention

238D 248 acrylic resin a a a The present invention

2390 251 Acrylic resin a a a The present invention

240D 255 acrylic resin a a a The present invention

241 D 257 acrylic resin a a a The present invention

242D 258 acrylic resin a a a The present invention

243D A acrylic resin d d d Comparative example

244D B acrylic resin c c d Comparative example

245D C acrylic resin ddd Comparative example] Optical filter No. Dye Binder Light resistance Heat resistance Moisture resistance Remarks

201 E 1 Polyester resin a a a The present invention

202E 3 Polyester resin a a a The present invention

203E 5 Polyester resin a a a The present invention

204E 1 5 Polyester resin b b a The present invention

205E 24 Polyester resin a a a The present invention

206 E 25 Polyester resin a b a The present invention

207 E 42 Polyester resin a a a The present invention

208 E 52 Polyester resin a a a The present invention

209 E 59 Polyester resin a a a The present invention

210E 62 Polyester resin a a a The present invention

21 1 E 71 Polyester resin a a a The present invention

212E 99 Polyester resin b a a The present invention

213E 100 Polyester resin b a a The present invention

214E 102 Polyester resin b b a The present invention

215E 103 Polyester resin a a a The present invention

216E 105 Polyester resin a a a The present invention

217E 1 22 Polyester resin a a a The present invention

218E 139 Polyester resin a a a The present invention

219E 1 0 Polyester resin a a a The present invention

220 E 141 Polyester resin a a a The present invention

221 E 142 Polyester resin a a a The present invention

222 E 143 Polyester resin a a a The present invention

223 E 145 Polyester resin a a a The present invention

224 E 147 Polyester resin a a a The present invention

225 E 148 Polyester resin a a a The present invention

226 E 158 Polyester resin a a a The present invention

227 E 165 Polyester resin a a a The present invention

228 E 169 Polyester resin a a a The present invention

229 E 176 Polyester resin a a b The present invention

230 E 192 Polyester resin b b a The present invention

231 E 193 Polyester resin a a b The present invention

232 E 199 Polyester resin a a a The present invention

233 E 218 Polyester resin a a a The present invention

234 E 224 Polyester resin b a a The present invention

235 E 230 Polyester resin a b b The present invention

236 E 238 Polyester resin b a a The present invention

237 E 244 Polyester resin a a a The present invention

238 E 248 Polyester resin a a a The present invention

239 E 251 Polyester resin a a a The present invention

240 E 255 Polyester resin a a a The present invention

241 E 257 Polyester resin a a a The present invention

242 E 258 Polyester resin a a a The present invention

243 E A Polyester resin d d d Comparative example

244 E B Polyester resin c c d Comparative example

245 EC polyester resin ddd comparative example] Optical filter No. Dye Binder Light resistance Heat resistance Moisture resistance Remarks

201 F 1 Ethylene vinyl acetate resin a a a The present invention

202 F 3 Ethylene vinyl acetate resin a a a The present invention

203 F 5 Ethylene vinyl acetate resin a a a The present invention

204 F 1 5 Ethylene vinyl acetate resin b b b Present invention

205 F 24 Ethylene vinyl acetate resin a a a The present invention

206 F 25 Ethylene vinyl acetate resin a a a The present invention

207 F 42 Ethylene vinyl acetate resin a a a The present invention

208 F 52 Ethylene vinyl acetate resin a a a The present invention

209 F 59 Ethylene vinyl acetate resin a a a The present invention

210F 62 Ethylene vinyl acetate resin a a a The present invention

21 1 F 71 Ethylene vinyl acetate resin a a a The present invention

212F 99 Ethylene vinyl acetate resin b a a The present invention

213F 100 Ethylene vinyl acetate resin b b a The present invention

214F 102 Ethylene vinyl acetate resin b b a The present invention

215 F 103 Ethylene vinyl acetate resin a a a The present invention

216F 105 Ethylene vinyl oxalate resin a a a The present invention

217F 122 Ethylene vinyl acetate resin a a a The present invention

Z18F 139 Ethylene vinyl acetate resin a a a The present invention

219F 140 Ethylene vinyl acetate resin a a a The present invention

220 F 141 Ethylene vinyl acetate resin a a a The present invention

221 F 142 Ethylene vinyl acetate resin a a a The present invention

222F 143 Ethylene vinyl acetate resin a a a The present invention

223 F 1 5 Ethylene vinyl acetate resin a a a The present invention

224 F 1 7 Ethylene vinyl acetate resin a a a The present invention

225 F 1 8 Ethylene vinyl acetate resin a a a The present invention

226 F 158 Ethylene vinyl acetate resin a a a The present invention

227 F 165 Ethylene vinyl acetate resin a a a The present invention

228 F 169 Ethylene vinyl acetate resin a a a The present invention

229 F 176 Ethylene vinyl acetate resin a a b The present invention

230 F 192 Ethylene vinyl acetate resin a a a The present invention

231 F 193 Ethylene vinyl acetate resin a b b Present invention

232F 199 Ethylene vinyl acetate resin a a a The present invention

233 F 218 Ethylene vinyl acetate resin a a b The present invention

234 F 224 Ethylene vinyl acetate resin b b a The present invention

235 F 230 Ethylene vinyl acetate resin a b b Present invention

236 F 238 Ethylene vinyl acetate resin b a a The present invention

237 F 244 Ethylene vinyl acetate resin a a a The present invention

238 F 248 Ethylene vinyl acetate resin a a a The present invention

239 F 251 Ethylene vinyl acetate resin a a a The present invention

240 F 255 Ethylene vinyl acetate resin a a a The present invention

241 F 257 Ethylene vinyl acetate resin a a a The present invention

Z42F 258 Ethylene vinyl acetate resin a a a The present invention

243F A Ethylene vinyl acetate resin d d d Comparative example

244F B Ethylene vinyl acetate resin c c d Comparative example

245F C Ethylene vinyl acetate resin d d d Comparative example

As is apparent from the table, the sample of the present invention has good light resistance, heat resistance and moisture resistance, whereas the comparative sample is inferior.

[0201] Example 3 (filter for display panel) (I) (Preparation of neon emission absorption filter)

 (3-1) Polyethylene terephthalate film (thickness 100 μm) is mixed with 0.3% methyl ethyl ketone / toluene mixed solution of the exemplified compound 24 of the present invention (methyl ethyl ketone / toluene = 1: 1) 0.5g, Polyester resin 20% methyl ethyl ketone / toluene mixed solution 6.5g After mixing with a bar coater, dry and apply neon luminescent absorption layer coating film with 5m thickness. Obtained. The transmittance curve of this coating film has a minimum value at 593 nm, and there is no other clear minimum value. The wavelength of the minimum value of visible light transmittance is 580 to 600 nm, which is the wavelength region of neon emission. Therefore, it was possible to provide a display panel filter having a high transmittance and suitable for cutting neon light emission.

 [0202] (3-2) A polyethylene terephthalate film (thickness lOO ^ m) was mixed with a 0.4% methyl ethyl ketone / toluene mixed solution of the exemplified compound 25 of the present invention (methyl ethyl ketone / toluene). = 1: 1) 0.6 g, 35% methyl ethyl ketone / toluene mixed solution of acrylic resin 4.0 g, mixed with bar coater and dried to absorb neon light with a thickness of 5 m A layer coating film was obtained. The transmittance curve of this coating film has a minimum value at 593 nm, and there is no other clear minimum value. The minimum wavelength of visible light transmittance is 580 to 600 nm, which is the wavelength range of neon emission. Therefore, it was possible to provide a display panel filter having a high transmittance and suitable for cutting neon light emission.

 [0203] (3-3) Polyethylene terephthalate film (thickness lOO ^ m) was mixed with a 0.4% methyl ethyl ketone / toluene mixed solution of the compound 42 of the present invention (methyl ethyl ketone / toluene). = 1: 1) 0.6 g, 35% methyl ethyl ketone / toluene mixed solution of acrylic resin 4.0 g, mixed with bar coater and dried to absorb neon light with a thickness of 5 m A layer coating film was obtained. The transmittance curve of this coating film has a minimum value of 595 nm, and there is no other clear minimum value. The minimum wavelength of visible light transmittance is 580 to 600 nm, which is the wavelength region of neon emission. Therefore, it was possible to provide a display panel filter having a high transmittance and suitable for cutting neon light emission.

[0204] (3-4) A polyethylene terephthalate film (thickness: 100 m) is mixed with a 0.3% methyl ethyl ketone / toluene mixed solution of the exemplified compound 52 of the present invention (methyl ethyl ketone / toluene = 1: 1) 0.6 g, 35% methyl ethyl ketone / toluene mixed solution of acrylic resin 4.0 After mixing g, it was coated with a bar coater and dried to obtain a 5 m thick neon light-emitting absorption layer coating film. The transmittance curve of this coating film has a minimum value at 586 nm, and there is no other clear minimum value. Therefore, it was possible to provide a display panel filter having a high transmittance and suitable for cutting neon light emission.

 [0205] (3-5) A polyethylene terephthalate film (thickness: 100 m) is mixed with a 0.3% methyl ethyl ketone / toluene mixed solution of the exemplified compound 140 of the present invention (methyl ethyl ketone / toluene = 1: 1) 0.6g, 35% methyl ethyl ketone / toluene mixed solution of acrylic resin 4.0g, mixed with bar coater, dried, and 5m thick neon light-emitting absorption layer A coating film was obtained. The transmittance curve of this coating film has a minimum value at 590 nm, and there is no other clear minimum value. The minimum wavelength of visible light transmittance is 580 to 600 nm, which is the wavelength region of neon emission. Therefore, it was possible to provide a display panel filter having a high transmittance and suitable for cutting neon light emission.

 [0206] (II) (Formation of UV absorbing layer)

 UV absorption containing isocyanate resin as binder and zinc oxide as UV absorber on the polyethylene terephthalate surface opposite to the neon light-emitting absorption layer surface of the display panel filter described in (31) to (3-5) above. The coating solution (manufactured by Sumitomo Osaka Cement Co., Ltd.) was coated with a bar coater and dried to form a 3 m thick UV absorbing layer. In each filter, the minimum wavelength of visible light transmittance was unchanged.

[0207] (III) (Formation of near-infrared absorbing layer)

Near-infrared absorbing dyes (N, N, N ′, N ′ —tetrakis (p) on the poly (ethylene terephthalate) surface opposite to the neon light-emitting absorption layer surface of the display panel filters (3 1) to (3-5) above Dibutylaminophenyl) p phenylene dimonium hexafluoroantimonate) 0.5% cyclohexanone solution 0.3g and polyester resin 20% cyclohexanone solution 3g were mixed and applied with a bar coater. And dried to form a 6m thick coating film. This filter was measured with a Hitachi spectrophotometer (U-3500). In each filter, the minimum wavelength of visible light transmittance did not change, and the wavelength at the minimum value of infrared transmittance was lOOnm. [0208] (IV) (Near-infrared absorber, formation example of composition mixed film of the present invention)

 (3-6) 0.5 g of a 0.5% cyclohexanone solution of the above near-infrared absorbing dye and 0.5 g of a 0.3% cyclohexanone solution of Exemplified Compound 24 of the present invention to 20% cyclohexane of a polyester resin Mixed with 6.5 g of xylene solution, coated on polyethylene terephthalate film (thickness: 100 mm) with a bar coater and dried to form a coating film with a thickness of 6 am, and produced a display panel filter. .

 [0209] (V) (Example of forming electromagnetic wave cut layer and non-glare layer)

 (3 7) Prepared by the above (2-6) on a polyethylene terephthalate film (thickness: 100 m) on which an ITO thin film was produced using argon gas and oxygen gas using an indium tin oxide oxide conjugate. A coating solution was used, and a near-infrared absorption layer and a neon emission absorption layer were laminated to a thickness of 6 m. In addition, a 3mm thick anti-glare layer on the opposite surface, a non-glare layer of PMMA plate with AR coating, and the ITO surface of the above filter were bonded together to produce a plasma display panel filter. I got a filter.

 [0210] (VI) (Comparative example)

 (3-8) A display panel filter having a near-infrared absorbing layer was obtained in the same manner as in (III) except that Comparative Compound D was used instead of Exemplified Compound 24 of the present invention. Comparative compound D is a 25:50:25 mixture of Exemplified Compounds I 34, I 35, and I 36 of JP-A-2005-197240.

[0211] [Chemical 55]

 (1 I 34)

 (1-35)

 (卜 36)

[0212] A front plate was prepared by separately bonding the filters prepared in (III), (IV), (V) and (VI) to glass, and this front plate was mounted on a plasma display. The plasma display was placed in an environmental room set at 45 ° C and 80% RH and used continuously for 24 hours. The color reproducibility after 24 hours was visually confirmed. The plasma display equipped with the front plate using the filter of the present invention ((IV), (IV), (V)) has a neon emission wavelength after 24 hours in an environment of 45 ° C and 80% RH. While it showed good color reproducibility without being affected by fluctuations, the plasma display equipped with the front plate using the filter (VI) of the comparative example has a 45 ° C, 80% RH environment. It was confirmed that the color reproducibility was obviously deteriorated due to the effect of fluctuations in the neon emission wavelength.

 [0213] As described above, by using the squarylium dye metal complex compound and binder of the present invention, an optical filter excellent in light resistance and heat-and-moisture resistance can be produced. It can be seen that the light resistance can be improved particularly in a high temperature and high humidity environment. Furthermore, by applying to front filters for displays, especially neon emission absorption filters that can effectively absorb neon emission, we were able to provide a display panel filter with good color reproducibility.

Claims

Claims: A script A filter having a maximum structure in the visible light region and having a partial structure represented by the following general formula (1).卜

 [Chemical formula 1] General formula (1)

(In the formula, M represents a metal atom, A represents an organic group, B represents a 5-membered ring, X represents an oxygen atom, a nitrogen atom or a sulfur atom, and Y represents a nitrogen atom when n = 0. , N = l represents a carbon atom, R represents a substituent, n represents 0 or 1, m represents an integer of 0 to 3. In the general formula (1), A represents an aryl 2. The optical filter according to claim 1, which is a group, a heterocyclic group, or the following general formula (1-A).

 [Chemical 2]

(In the formula, A ¹ represents a 5- or 6-membered ring, and R ¹ represents a hydrogen atom or a substituent.)

[3] The optical device according to claim 1 or 2, wherein in the general formula (1), the metal atom M is any one of copper, nickel, cobalt, zinc, aluminum, and beryllium. filter.

 [4] A display panel filter characterized by using any one of the claims 1 to 3 and the optical filter according to claim 1.