JP4967330B2 - Coloring composition, ink jet recording liquid, ink jet recording method, color toner, color filter, optical information recording medium, optical information recording method, and metal chelate dye - Google Patents

Description

  The present invention relates to a coloring composition, an inkjet recording liquid, an inkjet recording method, a color toner, a color filter, an optical information recording medium, an optical information recording method, and a metal chelate dye.

  Conventionally, as a method for obtaining a color hard copy, a color image recording technique has been studied by inkjet, electrophotography, silver halide photosensitive material, and the like. Color filters are used in electronic parts such as LCDs and PDPs for displays and CCDs for photographic equipment.

  Among these, the ink jet recording method is a recording method in which characters and images are obtained by directly ejecting and adhering ink droplets from a very fine nozzle to a recording member. This method has not only the advantage that the equipment used is low noise and good operability, but also the advantage that it can be easily colored and can use plain paper as a recording member, so it has been widely used in inkjet printers in recent years. ing.

  Ink-jet ink is compatible with the recording method used, has a high recording image density and good hue, excellent color image fastness such as light resistance, heat resistance and water resistance, recording medium On the other hand, it is required that fixing is fast and does not bleed after recording, that it is excellent in storage stability as ink, that there is no problem in safety such as toxicity and flammability, and that it is inexpensive. From such a viewpoint, various ink jet recording liquids have been proposed and studied, but there are very few recording liquids that satisfy many of the requirements at the same time.

  In color image recording using yellow, magenta, cyan, and black, for example, C.I. I. The conventionally known C.I. described in the index. I. Numbered dyes and pigments have been widely studied. For example, in magenta ink using a water-soluble dye, C.I. I. Xanthenes such as Acid Red 52, C.I. I. The one using an azo-based water-soluble dye such as Direct Red 20 is known, but the former has a problem of fastness such as light resistance, and the latter has a color reproducibility such as lack of vivid color tone. Had the problem of spectral absorption characteristics.

  On the other hand, as a method for improving the light resistance of a dye, a method of coordinating a metal with a dye is generally known, and this method is used for producing an ink jet dye, and a chelate pigment of a dye and a metal is contained in the ink. (For example, refer to Patent Documents 1 and 2). However, further improvements in the hue and light fastness levels have been desired. Further, an ink jet recording liquid containing an aqueous dispersion of polymer particles containing a metal coordinated to a dye has been proposed (see, for example, Patent Documents 3 and 4). There were drawbacks in terms of storage stability.

  As described above, it is difficult to satisfy all the performance items such as hue, fastness, and ink storage stability required for the ink-jet ink with the well-known dyes and pigments.

  In the case of using a colorant as a color toner, in a color copier or color laser printer using an electrophotographic method, a colorant is generally adhered to a toner in which a colorant is dispersed in resin particles or a resin particle surface. Toner is used. Since the method of attaching a coloring material to the resin surface is coloring only the surface, it is difficult to obtain a sufficient coloring effect. In addition, the charging performance may change due to separation from the surface of the colorant, and the surface of the fixing roller may be contaminated. Therefore, a toner in which a coloring material is dispersed inside a particle is widely used. The performance required for such a color toner includes color reproducibility, image transparency in an Over Head Projector (hereinafter referred to as OHP), and light resistance. Toners in which pigments are dispersed in particles as a colorant are disclosed (for example, refer to Patent Documents 5 and 6). However, these toners are excellent in light resistance, but are insoluble and thus easily aggregate and are transparent. The decrease in color and the hue change of the transmitted color are problems. On the other hand, a toner using a dye as a coloring material has been disclosed (see, for example, Patent Documents 7 to 9), and improvements have been seen in terms of transparency and hue, but it is still insufficient, and light resistance is a pigment. There was a problem that it deteriorated significantly as compared with the case of using.

  Since the color filter needs to have high transparency, a method called a dyeing method for coloring with a dye has been performed. For example, a photosensitive material to be dyed is applied to a substrate such as glass, followed by pattern exposure of one filter color, washing the unexposed portion in a development process, and removing the remaining pattern portion of the filter color. A color filter can be produced by sequentially repeating the operation of dyeing with a dye for all filter colors (see, for example, Patent Documents 10 and 11). This method uses dyes and has high transmittance, and the optical characteristics of the color filter are excellent, but there is a limit to light resistance, heat resistance, etc., and various colorants with excellent resistance and high transparency are desired. It was rare. Therefore, organic pigments having excellent light resistance and heat resistance have been used in place of dyes, but it has been difficult to obtain excellent optical properties such as dyes with color filters using pigments.

  Conventionally, an optical information recording medium (optical disk) capable of recording information only once by laser light is known. This optical disc is also called a write once disc (so-called CD-R), and its typical structure is a recording layer made of an organic dye on a transparent disk-shaped substrate, a light reflecting layer made of a metal such as gold, and a resin-made disc. The protective layer is provided in a laminated state in this order. Information is recorded on the CD-R by irradiating the CD-R with a near-infrared laser beam (usually a laser beam having a wavelength of about 780 nm), and the irradiated portion of the recording layer is irradiated with the light. As the temperature rises locally due to absorption of a chemical substance, a physical or chemical change (for example, generation of pits) occurs, and information is recorded by changing its optical characteristics. On the other hand, reading (reproduction) of information is also performed by irradiating laser light having the same wavelength as that of the recording laser light, and the portion where the optical characteristics of the recording layer have changed (recorded portion) and the portion not changed (unrecorded) Information is reproduced by detecting the difference in reflectance from (part).

  In recent years, an optical information recording medium having a higher recording density has been demanded. In response to such a demand, an optical disc called a write-once digital versatile disc (so-called DVD-R) has been proposed (see, for example, Non-Patent Document 1). In this DVD-R, the guide groove (pre-groove) for tracking the irradiated laser beam is narrower than half of the CD-R (0.74 to 0.8 μm) and is formed in a transparent disk shape. A recording layer made of a dye on a substrate, and usually two discs each having a light reflecting layer on the recording layer and a protective layer as necessary, or a disc-shaped protective substrate having the same shape as the disc It has a structure in which the recording layer is inside and bonded with an adhesive. Information recording / reproduction to / from DVD-R is performed by irradiating visible laser light (usually laser light having a wavelength in the range of 630 to 680 nm), and higher density recording than CD-R is possible. ing.

Since the DVD-R type information recording medium can record several times the amount of information as compared with the conventional CD-R type, the DVD-R type information recording medium has not only high recording sensitivity but also a large amount of information. Therefore, it is desirable that the error rate be small even for high-speed recording. In addition, since a recording layer made of a dye generally has low stability over time with respect to heat or light, it is desired to develop a recording layer that can maintain stable performance against heat or light over a long period of time. In order to improve sensitivity characteristics or stability important as the performance of such DVD-R, an optical disc using an azo dye has been conventionally used (for example, see Patent Document 12), or an optical disc using a cyanine dye. (For example, see Patent Document 13) is known, but its performance is not sufficient, and further improvement is desired.
Japanese Patent Laid-Open No. 10-72560 JP 2001-31896 A JP 2001-18880 A JP 2001-26731 A JP 62-157051 A Japanese Patent Laid-Open No. Sho 62-255556 JP-A-7-209912 Japanese Patent Laid-Open No. 10-20559 JP 2002-371214 A JP 2001-66421 A JP 2003-201411 A JP-A-11-130970 JP-A-10-226170 "Nikkei New Media" separate volume "DVD", 1995

  The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a novel metal chelate dye, a coloring composition containing a novel metal chelate dye, an inkjet recording liquid containing a novel metal chelate dye, To provide an ink jet recording method using the ink jet recording liquid, a color toner containing a novel metal chelate dye, a color filter, an optical information recording medium, and an optical information recording method using the optical information recording medium.

  The above object of the present invention has been achieved by the following constitution.

  1. The coloring composition characterized by containing the metal chelate pigment | dye which makes the pigment | dye represented by following General formula (1) a ligand.

(In the formula, R ₁ represents a hydrogen atom or a substituent, R ₂ represents a substituent, n represents an integer of 0 to 3, and when n is 2 or more, a plurality of R ₂ may be the same) G represents a chelatable group, A represents an aryl group or a heterocyclic group, and X forms a 5- to 6-membered nitrogen-containing heterocyclic ring together with the —N—C—N— moiety. Represents a group of non-metallic atoms necessary for
2. 2. The coloring composition as described in 1 above, wherein the dye represented by the general formula (1) is represented by the following general formula (2).

_{(Wherein, R 1, R 2, n} , R 1 in the G and A are the general formula _{(1), R 2, n} , .R 3 is synonymous with G and A represents a hydrogen atom or a substituent. )
3. At least a metal chelate dye having a ligand represented by the dye represented by the general formula (1) in the colored composition according to 1 or the dye represented by the general formula (2) in the colored composition according to 2 above. An ink jet recording liquid comprising one kind.

  4). 4. An ink jet recording method, wherein the ink jet recording liquid according to 3 is sprayed onto a recording medium for recording.

  5). At least a metal chelate dye having a ligand represented by the dye represented by the general formula (1) in the colored composition according to 1 or the dye represented by the general formula (2) in the colored composition according to 2 above. A color toner containing one kind.

  6). At least a metal chelate dye having a ligand represented by the dye represented by the general formula (1) in the colored composition according to 1 or the dye represented by the general formula (2) in the colored composition according to 2 above. A color filter comprising one type.

  7). At least a metal chelate dye having a ligand represented by the dye represented by the general formula (1) in the colored composition according to 1 or the dye represented by the general formula (2) in the colored composition according to 2 above. An optical information recording medium comprising a recording layer containing one kind.

  8). 8. An optical information recording method comprising recording information by irradiating the optical information recording medium described in 7 above with a laser beam selected from a range of 390 to 900 nm.

  9. A metal chelate dye having a ligand represented by the dye represented by the general formula (1) in the colored composition described in 1 or the dye represented by the general formula (2) in the colored composition described in 2 above.

  According to the present invention, a novel metal chelate dye, a colored composition containing the novel metal chelate dye, an ink jet recording liquid containing the novel metal chelate dye, an ink jet recording method using the ink jet recording liquid, and a novel metal chelate dye A color toner, a color filter, an optical information recording medium, and an optical information recording method using the optical information recording medium.

  Hereinafter, although the best mode for carrying out the present invention will be described, the present invention is not limited to these.

  First, the pigment | dye represented by the said General formula (1) based on this invention is explained in full detail.

In the general formula (1), R ₁ represents a hydrogen atom or a substituent, and R ₂ represents a substituent. The substituents represented by R ₁ and R ₂ are not particularly limited, and examples thereof include alkyl groups (for example, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, hexyl group, octyl group). , Dodecyl group, trifluoromethyl group, etc.), cycloalkyl group (eg, cyclopentyl group, cyclohexyl group, etc.), aryl group (eg, phenyl group, naphthyl group, etc.), acylamino group (eg, acetylamino group, benzoylamino group) Etc.), alkylthio groups (eg methylthio group, ethylthio group etc.), arylthio groups (eg phenylthio group, naphthylthio group etc.), alkenyl groups (eg vinyl group, 2-propenyl group, 3-butenyl group, 1-methyl group) -3-propenyl group, 3-pentenyl group, 1-methyl-3-butenyl group, 4-hexenyl Group, cyclohexenyl group, etc.), halogen atom (eg, fluorine atom, chlorine atom, bromine atom, iodine atom), alkynyl group (eg, propargyl group, etc.), heterocyclic group (eg, pyridyl group, thiazolyl group, oxazolyl group) Group, imidazolyl group, etc.), alkylsulfonyl group (eg, methylsulfonyl group, ethylsulfonyl group, etc.), arylsulfonyl group (eg, phenylsulfonyl group, naphthylsulfonyl group, etc.), alkylsulfinyl group (eg, methylsulfinyl group, etc.) Arylsulfinyl group (eg, phenylsulfinyl group), phosphono group, acyl group (eg, acetyl group, pivaloyl group, benzoyl group), carbamoyl group (eg, aminocarbonyl group, methylaminocarbonyl group, dimethylaminocarbonyl group) , Butyl Minocarbonyl group, cyclohexylaminocarbonyl group, phenylaminocarbonyl group, 2-pyridylaminocarbonyl group, etc.), sulfamoyl group (for example, aminosulfonyl group, methylaminosulfonyl group, dimethylaminosulfonyl group, butylaminosulfonyl group, hexylaminosulfonyl group) , Cyclohexylaminosulfonyl group, octylaminosulfonyl group, dodecylaminosulfonyl group, phenylaminosulfonyl group, naphthylaminosulfonyl group, 2-pyridylaminosulfonyl group, etc., sulfonamide group (for example, methanesulfonamide group, benzenesulfonamide group, etc.) ), Cyano group, alkoxy group (for example, methoxy group, ethoxy group, propoxy group, etc.), aryloxy group (for example, phenoxy group, naphthyloxy group, etc.) , Heterocyclic oxy group, siloxy group, acyloxy group (for example, acetyloxy group, benzoyloxy group, etc.), sulfonic acid group, sulfonic acid salt, aminocarbonyloxy group, amino group (for example, amino group, ethylamino group, Dimethylamino group, butylamino group, cyclopentylamino group, 2-ethylhexylamino group, dodecylamino group, etc.), anilino group (for example, phenylamino group, chlorophenylamino group, toluidino group, anisidino group, naphthylamino group, 2-pyridylamino group) Group), imide group, ureido group (for example, methylureido group, ethylureido group, pentylureido group, cyclohexylureido group, octylureido group, dodecylureido group, phenylureido group, naphthylureido group, 2-pyridylaminoureido group, etc. ) Lucoxycarbonylamino group (eg methoxycarbonylamino group, phenoxycarbonylamino group etc.), alkoxycarbonyl group (eg methoxycarbonyl group, ethoxycarbonyl group, phenoxycarbonyl etc.), aryloxycarbonyl group (eg phenoxycarbonyl group etc.) ), Heterocyclic thio groups, thioureido groups, carboxyl groups, carboxylic acid salts, hydroxy groups, mercapto groups, nitro groups, and the like. These substituents may be further substituted with the same substituent.

In the general formula (1), R ₁ is preferably an alkyl group or an aryl group, more preferably an alkyl group, and particularly preferably a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group.

In the general formula (1), n represents an integer of 0 to 3, and when n is 2 or more, a plurality of R ₂ may be the same or different, but n is preferably 0 to 1.

In general formula (1), R ₂ may combine with G described below to form a ring. G represents a chelatable group, for example, hydroxyl group, alkoxy group, aryloxy group, mercapto group, alkylthio group, arylthio group, amino group, anilino group, alkoxycarbonyl group, acyloxy group, sulfamoyl group, sulfonamide group, Examples thereof include a carbamoyl group, an amide group, and a carboxy group. Of these, a hydroxyl group, an alkoxy group, and an amino group are preferable. As described above, G may be bonded to R ₂ to form a ring. For example, G may form a ring such as a quinoline ring, a tetrahydroquinoline ring, a chroman ring, a thiochroman ring, a benzoquinazolone ring, or a benzothiadiazine ring. May be. These rings may have a substituent, and examples of the substituent include the same groups as those described above for R _1, and may be further substituted with the same substituent.

In general formula (1), A represents an aryl group or a heterocyclic group. Table The aryl group and heterocyclic group represented, the R ₁ of the mentioned beneath which an aryl group and the heterocyclic group and the same group can be cited as examples of the substituent, further these said R ₁ in A It may be substituted with a group similar to the substituent to be formed.

In the general formula (1), X represents a nonmetallic atom group necessary for forming a 5- to 6-membered nitrogen-containing heterocyclic ring together with the —N—C—N— moiety. Specifically, it forms a 5- to 6-membered ring skeleton in which the constituent atoms or groups of the ring skeleton are selected from carbon atoms, oxygen atoms, sulfur atoms, nitrogen atoms, carbonyl groups, sulfonyl groups, and phosphonyl groups. Represents a nonmetallic atom group. Preferred X is a nonmetallic atom group forming a 5- to 6-membered ring skeleton in which the constituent atoms or groups of the ring skeleton are selected from carbon atoms, nitrogen atoms, and carbonyl groups. These may have a substituent represented by, for example, R ₁ in the above general formula (1), or may be condensed with another ring.

  The general formula (1) specifically includes the general formula (2), and further the general formulas (1-a), (1-b), (1-c), (1-d), (1- e), (1-f) or (1-g), of which general formulas (2), (1-a), (1-b), (1-c) and ( 1-e) is preferred, and general formula (2) is particularly preferred.

Wherein, R _1, R _2, n, G and A, the R ₁ in the general formula _{(1), R 2, n} , is synonymous with G and A. In the general formulas (1-a) to (1-g), R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ , R ₁₁ and R ₁₂ represent a hydrogen atom or a substituent. When these represent a substituent, the substituent is not particularly limited, and examples thereof include the same groups as the substituent represented by R ₁ . These substituents may be further substituted with the same substituent. m represents an integer of 0 to 4, and m is preferably 0 or 1. When m represents an integer greater than or equal to 2, several R < ₇ > may be the same or different.

In the general formula _{(2), R 1, R} 2, n, G and A, the R ₁ in the general formula _{(1), R 2, n} , is synonymous with G and A.

In the general formula (2), R ₃ represents a hydrogen atom or a substituent. Examples of the substituent represented by R ₃ include the same groups as the substituent represented by R ₁ in the general formula (1), and these substituents may be further substituted with the same substituents. Good. R ₃ is preferably an alkyl group or an aryl group.

  The dye represented by the general formula (2) according to the present invention is preferably a dye represented by the following general formula (3).

_{Wherein, R 1, R 2, R} 3, n, G and _{A, R 1, R 2, R} 3 in the general formula (2), n, is synonymous with G and A.

  The compound represented by the general formula (1) may be bonded at an arbitrary position to form a multimer. In this case, each unit may be the same as or different from each other, and polystyrene, polymethacrylate, You may couple | bond with polymer chains, such as polyvinyl alcohol and a cellulose.

  The azo group in the compound represented by the general formula (1) or (2) according to the present invention takes an azo type (—N═N—) or a hydrazo type (═N—NH—) depending on the structure of the compound. However, in the present invention, all are described in the azo form. Even when other tautomers exist, they are described in one of the representative forms in the present invention, but tautomers different from those described in the present invention are also included in the compounds of the present invention. .

  Hereinafter, although the specific example of the pigment | dye represented by the said General formula (1) or (2) is shown, this invention is not limited by the following specific examples.

  Next, the metal chelate dye having the dye represented by the general formula (1) or (2) according to the present invention as a ligand will be described.

  The metal chelate dye having the dye represented by the general formula (1) or (2) as a ligand is preferably a reaction between the dye represented by the general formula (1) or (2) and a divalent metal salt. Can be obtained. The method of synthesizing the metal chelate dye can be synthesized according to the method described in “Chelate Chemistry (5) Complex Chemistry Experimental Method [I] (Edited by Nanedo)”. Divalent metal salts used include nickel chloride, nickel acetate, magnesium compounds represented by magnesium chloride, calcium compounds represented by calcium chloride, barium chloride, zinc chloride, zinc acetate, titanium (II) chloride, Examples thereof include iron (II) chloride, copper (II) chloride, cobalt chloride, and manganese (II) chloride. Preferred are nickel chloride, nickel acetate, copper chloride, copper acetate, cobalt chloride, zinc chloride, and zinc acetate. The metal chelate dye used in the present invention may have a neutral ligand depending on the central metal, and typical ligands include water, alcohols, and amines.

  Furthermore, you may obtain by making the pigment | dye represented by the said General formula (1) or (2) react with the metal ion containing compound represented below.

The metal ion-containing compound is preferably an organic salt of a metal ion or a metal complex. Examples of the metal include monovalent and polyvalent metals belonging to Groups I to VIII of the Periodic Table. Among them, Al, Co, Cr, Cu, Fe, Mg, Mn, Mo, Ni, Sn, Ti, and Zn Ni, Cu, Cr, Co and Zn are more preferable, Ni and Cu are further preferable, and Ni is particularly preferable. Specific examples of the metal ion-containing compound include Ni ²⁺ , Cu ²⁺ , Cr ²⁺ , Co ²⁺ and Zn ²⁺ and aliphatic salts such as acetic acid and stearic acid, or fragrances such as benzoic acid and salicylic acid. In addition to the salts of group carboxylic acids, the metal ion-containing compound represented by the following general formula (4) can be particularly preferably used.

General formula (4) [X (Q1) _a (Q2) _b (Q3) _c ] ^{P +} (Y ⁻ ) _P
In the general formula (4), X represents a metal ion, preferably Ni ²⁺ , Cu ²⁺ , Cr ²⁺ , Co ²⁺ , Zn ²⁺ , more preferably Ni ²⁺ , Cu ²⁺ , Zn ^2+. And particularly preferably represents Ni ²⁺ . Q1, Q2, and Q3 each represent a coordination compound capable of coordinating with the metal represented by X, and may be the same or different from each other. These coordination compounds can be selected from, for example, coordination compounds described in the above-mentioned chelate science (5) (Nan Edo). Y ^- is represents an organic anion group, and specific examples include tetraphenyl boron anion and alkylbenzene sulfonate anion. a represents an integer of 1, 2 or 3; b represents 1, 2 or 0; c represents 1 or 0; in these, the complex represented by the above general formula is tetradentate or hexadentate It is determined depending on whether it is coordinated or determined based on the number of ligands of Q1, Q2, and Q3. P represents 0, 1 or 2. In P = 0, the coordination compounds represented by Q1, Q2, and Q3 are anionic compounds, and an anionic compound represented by Q1, Q2, and Q3 and a metal ion represented by X (also referred to as a metal cation). ) Is electrically neutralized.

  The coloring composition of the present invention is obtained by reacting the dye represented by the general formula (1) or (2) with the divalent metal salt or the metal ion-containing compound represented by the general formula (4). The metal chelate dye in the coloring composition is obtained by using a metal chelate dye synthesized in advance, or a dye and a metal salt or metal ion. It is also possible to use a metal chelate dye produced by reacting in a colored composition using each of the containing compounds separately. In the latter case, the mixing ratio (molar ratio) of the dye and the metal salt or metal ion-containing compound is not limited. When the dye: metal salt or metal ion-containing compound = 1: N, N is preferably 0.01 to 100, More preferably, it represents 0.1-10, More preferably, it represents 0.3-5.

  The metal chelate dye is dissolved in a metal salt or metal ion-containing compound powder or an organic solvent in a solution obtained by dissolving or dispersing the dye represented by the general formula (1) or (2) in an organic solvent. It is made by adding a solution. The metal chelate dye may be isolated as a crystal. If isolation is difficult, the solvent may be distilled off and the residue may be used. The residue may be dissolved in another solvent and used. Also good.

  Specific examples of the metal salt and the metal ion-containing compound represented by the general formula (4) are given below, but the present invention is not limited thereto.

  The metal chelate dye having the dye represented by the general formula (1) or (2) as a ligand is preferably represented by the following general formula (5).

General formula (5) M ^{Q +} (D) _d (L ⁻ ) _Q
In general formula (5), M represents a metal, preferably represents Ni, Cu, Cr, Co, or Zn, more preferably represents Ni, Cu, or Zn, and particularly preferably represents Ni. Q represents an integer of 1 to 3, preferably 2 or 3, and particularly preferably 2. That is, M ^{Q +} represents a metal ion, preferably represents Ni ²⁺ , Cu ²⁺ , Cr ²⁺ , Co ²⁺ , Zn ²⁺ , and more preferably represents Ni ²⁺ , Cu ²⁺ , Zn ²⁺ . Particularly preferably, it represents Ni ²⁺ .

In general formula (5), D represents the pigment | dye represented by the said general formula (1) or (2), d represents the integer of 1-3, and 1 or 2 is preferable. In the general formula (5), L ⁻ represents an anion (also referred to as an anion).

  Hereinafter, although the specific example of the metal chelate pigment | dye which uses the pigment | dye represented by the said General formula (1) or (2) as a ligand is shown, this invention is not limited by the following specific examples.

  Hereinafter, the coloring composition characterized by containing the metal chelate pigment | dye which makes the pigment | dye represented by the said General formula (1) or (2) a ligand is demonstrated.

  The colored composition of the present invention is not particularly limited as long as it is a colored composition containing a metal chelate dye having the dye represented by the general formula (1) or (2) as a ligand.

  It is known that a metal chelate dye formed of a dye and a metal has excellent performance in light resistance and wet heat fastness compared to a dye before chelation. Furthermore, the spectral absorption characteristics of the dye may change due to chelation with a metal, and there are merits in color reproduction such as an increase in molar extinction coefficient and sharpening to provide a good hue.

  Next, the ink jet recording liquid, ink jet recording method, color toner, and color filter of the present invention will be described in detail.

  The ink jet recording liquid of the invention contains at least one metal chelate dye having a dye represented by the general formula (1) or a dye represented by the general formula (2) as a ligand. In addition, a metal chelate dye having a dye other than the present invention as a ligand may be contained.

  The ink jet recording liquid of the present invention can use various solvent systems such as an aqueous solvent, an oil-based solvent, a solid (phase change) solvent, and the like, and the effects of the present invention are exhibited particularly when an aqueous solvent is used. As the aqueous solvent, water (for example, ion-exchanged water is preferable) and a water-soluble organic solvent are generally used.

  Examples of water-soluble organic solvents include alcohols (eg, methanol, ethanol, propanol, isopropanol, butanol, isobutanol, secondary butanol, tertiary butanol, benzyl alcohol, etc.), polyhydric alcohols (eg, ethylene glycol, diethylene glycol) , Triethylene glycol, polyethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, butylene glycol, hexanediol, pentanediol, glycerin, hexanetriol, thiodiglycol, etc.), polyhydric alcohol ethers (eg, ethylene glycol monomethyl ether) , Ethylene glycol monoethyl ether, ethylene glycol monobutyl ether, diethylene glycol Monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monobutyl ether, ethylene glycol monomethyl ether acetate, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, ethylene glycol monophenyl ether, propylene glycol Monophenyl ether, etc.), amines (eg, ethanolamine, diethanolamine, triethanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, morpholine, N-ethylmorpholine, ethylenediamine, diethylenediamine, triethylenetetramine, tetraethylenepentamine) The Ethyleneimine, pentamethyldiethylenetriamine, tetramethylpropylenediamine, etc.), amides (eg, formamide, N, N-dimethylformamide, N, N-dimethylacetamide, etc.), heterocyclics (eg, 2-pyrrolidone, N-methyl) -2-pyrrolidone, cyclohexyl pyrrolidone, 2-oxazolidone, 1,3-dimethyl-2-imidazolidinone, etc.), sulfoxides (eg dimethyl sulfoxide etc.), sulfones (eg sulfolane etc.), urea, acetonitrile, acetone Etc.

  In the aqueous solvent as described above, the dye represented by the general formula (1) or the metal chelate dye having the dye represented by the general formula (2) as a ligand is soluble in the solvent system. Then, it can be dissolved and used as it is.

  On the other hand, when the metal chelate dye having the dye represented by the general formula (1) or the dye represented by the general formula (2) as a ligand is insoluble in the solvent system as it is, it is required. Metal chelate dyes are finely divided using various dispersing machines (for example, ball mill, sand mill, attritor, roll mill, agitator mill, Henschel mixer, colloid mill, ultrasonic homogenizer, pearl mill, jet mill, ang mill, etc.) After the metal chelate dye is dissolved in a soluble organic solvent, it can be dispersed in the solvent system together with a polymer dispersant or a surfactant. Further, when the liquid is insoluble liquid or semi-molten as it is, it can be dissolved as it is or dissolved in a soluble organic solvent and dispersed in the solvent system together with the polymer dispersant or the surfactant.

  When the metal chelate dye having the dye represented by the general formula (1) or the dye represented by the general formula (2) of the present invention as a ligand is insoluble in the solvent system, it is made fine particles. It is preferably dispersed in the solvent system, and more preferably dispersed in fine particles having an average particle size of 150 nm or less.

  The average particle diameter is a volume average particle diameter, and a circle-converted average particle diameter obtained from an average value of a projected area of a transmission electron microscope (TEM) photograph (obtained for at least 100 particles or more) Is required. The coefficient of variation can be determined by determining the volume average particle size and its standard deviation and dividing the standard deviation by the volume average particle size. Alternatively, the volume average particle diameter and the standard deviation thereof can be obtained using a dynamic light scattering method. For example, it can be determined using a laser particle size analysis system manufactured by Otsuka Electronics or a Zetasizer manufactured by Malvern.

  In addition, the metal chelate dye is dissolved in an organic solvent in which the dye represented by the general formula (1) or the dye represented by the general formula (2) of the present invention is soluble. After that, it is preferably dispersed in an aqueous solvent as a fine particle dispersion together with the oil-soluble polymer.

  Specific examples of the method for preparing the aqueous solvent used for such an ink jet recording liquid include, for example, JP-A Nos. 5-148436, 5-295212, 7-97541, 7-82515 and 7. Reference can be made to the methods described in the publications of -1185854.

  Next, the oil-soluble polymer will be described.

  There is no restriction | limiting in particular as said oil-soluble polymer, Although it can select suitably according to the objective, A vinyl polymer is mentioned suitably. Examples of the vinyl polymer include conventionally known ones, which may be any of a water-insoluble type, a water-dispersed (self-emulsifying) type, and a water-soluble type. The water dispersion type is preferable.

  The water-dispersible vinyl polymer may be any of an ion dissociation type, a non-ionic dispersible group-containing type, or a mixture thereof.

  Examples of the ion dissociation type vinyl polymer include a vinyl polymer containing a cationic dissociable group such as a tertiary amino group and a vinyl polymer containing an anionic dissociative group such as carboxylic acid and sulfonic acid. Examples of the nonionic dispersible group-containing vinyl polymer include vinyl polymers containing a nonionic dispersible group such as a polyethyleneoxy chain. Among these, an ion dissociation type vinyl polymer containing an anionic dissociable group, a nonionic dispersible group containing type vinyl polymer, and a mixed type vinyl polymer are preferable from the viewpoint of dispersion stability of the colored fine particles.

  As a monomer which forms the said vinyl polymer, the following are mentioned, for example. That is, acrylic esters, specifically, methyl acrylate, ethyl acrylate, n-propyl acrylate, isopropyl acrylate, n-butyl acrylate, isobutyl acrylate, sec-butyl acrylate, tert-butyl acrylate, amyl acrylate, hexyl acrylate, 2 -Ethylhexyl acrylate, octyl acrylate, tert-octyl acrylate, 2-chloroethyl acrylate, 2-bromoethyl acrylate, 4-chlorobutyl acrylate, cyanoethyl acrylate, 2-acetoxyethyl acrylate, benzyl acrylate, methoxybenzyl acrylate, 2-chlorocyclohexyl Acrylate, cyclohexyl acrylate, furfuryl acrylate, tetrahydride Furfuryl acrylate, phenyl acrylate, 5-hydroxypentyl acrylate, 2,2-dimethyl-3-hydroxypropyl acrylate, 2-methoxyethyl acrylate, 3-methoxybutyl acrylate, 2-ethoxyethyl acrylate, 2-butoxyethyl acrylate, 2 -(2-methoxyethoxy) ethyl acrylate, 2- (2-butoxyethoxy) ethyl acrylate, glycidyl acrylate, 1-bromo-2-methoxyethyl acrylate, 1,1-dichloro-2-ethoxyethyl acrylate, 2,2, Examples include 2-tetrafluoroethyl acrylate, 1H, 1H, 2H, 2H-perfluorodecyl acrylate and the like.

  Methacrylic acid esters, specifically, methyl methacrylate, ethyl methacrylate, n-propyl methacrylate, isopropyl methacrylate, n-butyl methacrylate, isobutyl methacrylate, sec-butyl methacrylate, tert-butyl methacrylate, amyl methacrylate, hexyl methacrylate, cyclohexyl methacrylate , Benzyl methacrylate, chlorobenzyl methacrylate, octyl methacrylate, stearyl methacrylate, 2- (3-phenylpropyloxy) ethyl methacrylate, furfuryl methacrylate, tetrahydrofurfuryl methacrylate, phenyl methacrylate, cresyl methacrylate, naphthyl methacrylate, 2-hydroxyethyl methacrylate 4-Hido Xylbutyl methacrylate, triethylene glycol monomethacrylate, dipropylene glycol monomethacrylate, 2-methoxyethyl methacrylate, 3-methoxybutyl methacrylate, 2-ethoxyethyl methacrylate, 2-iso-propoxyethyl methacrylate, 2-butoxyethyl methacrylate, 2- (2-methoxyethoxy) ethyl methacrylate, 2- (2-ethoxyethoxy) ethyl methacrylate, 2- (2-butoxyethoxy) ethyl methacrylate, 2-acetoxyethyl methacrylate, 2-acetoacetoxyethyl methacrylate, allyl methacrylate, glycidyl methacrylate, 2,2,2-tetrafluoroethyl methacrylate, 1H, 1H, 2H, 2H-perfluorodecyl methacrylate Such as over doors and the like.

  Vinyl esters, specifically vinyl acetate, vinyl propionate, vinyl butyrate, vinyl isobutyrate, vinyl caproate, vinyl chloroacetate, vinyl methoxyacetate, vinyl phenyl acetate, vinyl benzoate, vinyl salicylate, etc. Is mentioned.

  Acrylamides, specifically, acrylamide, methyl acrylamide, ethyl acrylamide, propyl acrylamide, butyl acrylamide, tert-butyl acrylamide, tert-octyl acrylamide, cyclohexyl acrylamide, benzyl acrylamide, hydroxymethyl acrylamide, methoxymethyl acrylamide, butoxymethyl acrylamide, Examples include methoxyethyl acrylamide, phenyl acrylamide, dimethyl acrylamide, diethyl acrylamide, β-cyanoethyl acrylamide, N- (2-acetoacetoxyethyl) acrylamide, diacetone acrylamide, and the like.

  Methacrylamide, specifically, methacrylamide, methyl methacrylamide, ethyl methacrylamide, propyl methacrylamide, butyl methacrylamide, tert-butyl methacrylamide, cyclohexyl methacrylamide, benzyl methacrylamide, hydroxymethyl methacrylamide, methoxyethyl methacryl Examples include amide, phenylmethacrylamide, dimethylmethacrylamide, β-cyanoethylmethacrylamide, N- (2-acetoacetoxyethyl) methacrylamide.

  Olefins, specifically dicyclopentadiene, ethylene, propylene, 1-butene, 1-pentene, vinyl chloride, vinylidene chloride, isoprene, chloroprene, butadiene, 2,3-dimethylbutadiene, styrenes such as styrene Methyl styrene, dimethyl styrene, trimethyl styrene, ethyl styrene, isopropyl styrene, chloromethyl styrene, methoxy styrene, acetoxy styrene, chloro styrene, dichloro styrene, bromo styrene, vinyl benzoic acid methyl ester and the like.

  Examples of vinyl ethers include methyl vinyl ether, butyl vinyl ether, hexyl vinyl ether, and methoxyethyl vinyl ether.

  Other monomers include butyl crotonate, hexyl crotonate, dimethyl itaconate, dibutyl itaconate, diethyl maleate, dimethyl maleate, dibutyl maleate, diethyl fumarate, dimethyl fumarate, dibutyl fumarate, methyl vinyl ketone, phenyl Vinyl ketone, methoxyethyl vinyl ketone, N-vinyl oxazolidone, N-vinyl pyrrolidone, vinylidene chloride, methylene malonnitrile, vinylidene, diphenyl-2-acryloyloxyethyl phosphate, diphenyl-2-methacryloyloxyethyl phosphate, dibutyl-2-acryloyl Examples thereof include oxyethyl phosphate and dioctyl-2-methacryloyloxyethyl phosphate.

  Examples of the monomer having a dissociable group include a monomer having an anionic dissociable group and a monomer having a cationic dissociable group. Examples of the monomer having an anionic dissociable group include a carboxylic acid monomer, a sulfonic acid monomer, and a phosphoric acid monomer.

  Examples of the carboxylic acid monomer include acrylic acid, methacrylic acid, itaconic acid, maleic acid, fumaric acid, citraconic acid, crotonic acid, itaconic acid monoalkyl esters (for example, itaconic acid monomethyl, itaconic acid monoethyl, itaconic acid monobutyl, etc. ), Maleic acid monoalkyl esters (for example, monomethyl maleate, monoethyl maleate, monobutyl maleate, etc.).

  Examples of the sulfonic acid monomer include styrene sulfonic acid, vinyl sulfonic acid, acryloyloxyalkyl sulfonic acid (for example, acryloyloxymethyl sulfonic acid, acryloyloxyethyl sulfonic acid, acryloyloxypropyl sulfonic acid, etc.), methacryloyloxyalkyl sulfonic acid. (For example, methacryloyloxymethylsulfonic acid, methacryloyloxyethylsulfonic acid, methacryloyloxypropylsulfonic acid, etc.), acrylamide alkylsulfonic acid (for example, 2-acrylamido-2-methylethanesulfonic acid, 2-acrylamido-2-methylpropanesulfone, etc.) Acid, 2-acrylamido-2-methylbutanesulfonic acid, etc.), methacrylamide alkylsulfonic acid (for example, 2-methacrylic acid) 2-methyl-ethanesulfonic acid, 2-methacrylamide-2-methylpropanesulfonic acid, 2-methacrylamide-2-methylbutanesulfonic acid).

  Examples of the phosphoric acid monomer include vinylphosphonic acid and methacryloyloxyethylphosphonic acid.

  Among these, acrylic acid, methacrylic acid, styrene sulfonic acid, vinyl sulfonic acid, acrylamide alkyl sulfonic acid, and methacrylamide alkyl sulfonic acid are preferable. Acrylic acid, methacrylic acid, styrene sulfonic acid, 2-acrylamido-2-methylpropane sulfone Acid, 2-acrylamido-2-methylbutanesulfonic acid is more preferable.

  Examples of the monomer having a cationic dissociable group include monomers having a tertiary amino group such as dialkylaminoethyl methacrylate and dialkylaminoethyl atacrylate.

  Examples of the monomer containing a nonionic dispersible group include esters of polyethylene glycol monoalkyl ether and carboxylic acid monomers, esters of polyethylene glycol monoalkyl ether and sulfonic acid monomers, polyethylene glycol monoalkyl ether and phosphoric acid. Examples thereof include an ester with a monomer, a vinyl group-containing urethane formed from a polyethylene glycol monoalkyl ether and an isocyanate group-containing monomer, and a macromonomer containing a polyvinyl alcohol structure. As a repeating number of the ethyleneoxy part of the said polyethylene glycol monoalkyl ether, 8-50 are preferable and 10-30 are more preferable. The number of carbon atoms in the alkyl group of the polyethylene glycol monoalkyl ether is preferably 1-20, and more preferably 1-12.

  These monomers may be used alone to form a vinyl polymer, or two or more may be used in combination to form a vinyl polymer. The purpose of the vinyl polymer (Tg adjustment, solubility) It can be appropriately selected according to improvement, dispersion stability, etc.

  The oil solvent used in the present invention is an organic solvent.

  Examples of oil-based solvents include alcohols (for example, pentanol, heptanol, octanol, phenylethyl alcohol, phenylpropyl alcohol, furfuryl alcohol, anis alcohol, etc.), esters (for example, ethylene glycol diacetate, ethylene glycol monomethyl). Ether acetate, diethylene glycol monomethyl ether acetate, propylene glycol diacetate, ethyl acetate, amyl acetate, benzyl acetate, phenylethyl acetate, phenoxyethyl acetate, ethyl phenylacetate, benzyl propionate, ethyl benzoate, butyl benzoate, butyl laurate, Isopropyl myristate, triethyl phosphate, tributyl phosphate, diethyl phthalate, dibutyl phthalate, diethyl malonate, dimalonate Lopyl, diethyl diethylmalonate, diethyl succinate, dibutyl succinate, diethyl glutarate, diethyl adipate, dipropyl adipate, dibutyl adipate, di (2-methoxyethyl) adipate, diethyl sebacate, diethyl maleate, malee Dibutyl acid, dioctyl maleate, diethyl fumarate, dioctyl fumarate, cinnamic acid-3-hexenyl, etc.), ethers (eg, butyl phenyl ether, benzyl ethyl ether, hexyl ether, etc.), ketones (eg, benzyl methyl) Ketones, benzylacetone, diacetone alcohol, cyclohexanone, etc.), hydrocarbons (eg petroleum ether, petroleum benzyl, tetralin, decalin, tertiary amylbenzene, dimethylnaphthalene, etc.), amides (eg If, N, N-diethyldodecanamide, etc.).

  The oil-based solvent as described above is used by dissolving the dye represented by the general formula (1) or the metal chelate dye having the dye represented by the general formula (2) as a ligand as it is. It can also be used by dispersing or dissolving in combination with a resinous dispersant or binder.

  For the specific method for preparing the oil-based solvent used in such an ink jet recording liquid, methods described in JP-A-3-231975 and JP-A-5-508883 can be referred to.

  The solid (phase change) solvent used in the present invention is a phase change solvent that is a solid at room temperature as a solvent and is in a molten liquid state when the inkjet recording liquid is heated and jetted.

  Such phase change solvents include natural waxes (eg, beeswax, carnauba wax, rice wax, wood wax, jojoba oil, whale wax, candelilla wax, lanolin, montan wax, ozokerite, ceresin, paraffin wax, microwax. Crystallin wax, petrolactam, etc.), polyethylene wax derivatives, chlorinated hydrocarbons, organic acids (eg palmitic acid, stearic acid, behenic acid, tiglic acid, 2-acetonaphthone behenic acid, 12-hydroxystearic acid, dihydroxystearic acid) Acid), organic acid esters (for example, esters of the above-mentioned organic acids with alcohols such as glycerin, diethylene glycol, and ethylene glycol), alcohols (for example, dodecanol, tetradecanol, hexadecanol, eicosano) , Docosanol, tetracosanol, hexacosanol, octacosanol, dodecenol, myricyl alcohol, tetracenol, hexadecenol, eicosenol, docosenol, pinene glycol, hinokiol, butynediol, nonanediol, isophthalyl alcohol, mesythelin, teleaphthalyl alcohol , Hexanediol, decanediol, dodecanediol, tetradecandiol, hexadecanediol, docosandiol, tetracosanediol, tvneol, phenylglycerin, eicosanediol, octanediol, phenylpropylene glycol, bisphenol A, paraalphacumylphenol Etc.), ketones (eg benzoylacetone, diacetobenzene, benzophenone, tricho Non, heptacosanone, heptatriacontanone, hentriacontanone, heptatriacontanone, stearone, laurone, dianisole, etc.), amides (eg oleic acid amide, lauric acid amide, stearic acid amide, ricinoleic acid amide, palmitic acid amide) , Tetrahydrofuranic acid amide, erucic acid amide, myristic acid amide, 12-hydroxystearic acid amide, N-stearyl erucic acid amide, N-oleyl stearic acid amide, N, N'-ethylenebislauric acid amide, N, N'- Ethylene bis stearic acid amide, N, N'-ethylene bis oleic acid amide, N, N'-methylene bis stearic acid amide, N, N'-ethylene bis behenic acid amide, N, N'-xylylene bis stearic acid amide , N, N'-Buchi Lenbis stearic acid amide, N, N′-dioleyl adipic acid amide, N, N′-distearyl adipic acid amide, N, N′-dioleyl sebacic acid amide, N, N′-cysteallyl sebacic acid amide, Like N, N'-distearyl terephthalamide, N, N'-distearylisophthalamide, phenacetin, toluamide, acetamide, oleic acid dimer / ethylenediamine / stearic acid (1: 2: 2 molar ratio) A reaction product of dimer acid, diamine and fatty acid such as tetraamide), sulfonamide (eg, paratoluenesulfonamide, ethylbenzenesulfonamide, butylbenzenesulfonamide, etc.), silicones (eg, silicone SH6018 (Toray Silicone), Silicone KR215, 216, 220 (Shin-Etsu Corn), etc.), coumarones (for example, Escron G-90 (Nippon Chemical Co., Ltd.)), cholesterol fatty acid esters (for example, stearic acid cholesterol, palmitic acid cholesterol, myristic acid cholesterol, behenic acid cholesterol, lauric acid cholesterol, melisin) Acid cholesterol, etc.), saccharide fatty acid esters (for example, sucrose stearate, sucrose palmitate, saccharose behenate, saccharose laurate, saccharose melicinate, lactose stearate, lactose palmitate, lactose myristate, lactose behenate, lactose laurate) , Lactose melicinate, etc.).

  The phase change temperature in the solid-liquid phase change of the solid (phase change) solvent is preferably 60 to 200 ° C, and more preferably 80 to 150 ° C. The solid (phase change) solvent as described above is prepared by mixing the dye represented by the general formula (1) or the dye represented by the general formula (2) of the present invention with a ligand in a heated molten solvent. The metal chelate dye to be dissolved can be used as it is, or can be used by being dispersed or dissolved in combination with a resinous dispersant or a binder.

  For specific methods for preparing such phase change solvents, the methods described in JP-A Nos. 5-186723 and 7-70490 can be referred to.

  Using a water-based, oil-based, or solid (phase change) solvent as described above, the dye represented by the general formula (1) or the dye represented by the general formula (2) of the present invention is used as a ligand. The ink jet recording liquid of the present invention in which the metal chelate dye is dissolved or dispersed is preferably 40 cP or less, more preferably 30 cP or less, as the viscosity at the time of flight.

The ink jet recording liquid of the present invention preferably has a surface tension during flight of 2 × 10 ⁻⁴ to 10 ⁻³ N / cm, more preferably 3 × 10 ⁻⁴ to 8 × 10 ⁻⁴ N / cm. preferable.

  The metal chelate dye of the present invention is preferably used in the range of 0.1 to 25% by mass of the ink jet recording liquid, and more preferably in the range of 0.5 to 10% by mass.

  The resin-type dispersant used in the present invention is preferably a polymer compound having a molecular weight of 1,000 to 1,000,000. When these are used, 0.1 to 50% by mass in the ink jet recording liquid is used. It is preferable to contain.

  The inkjet recording liquid of the present invention includes a viscosity modifier, a surface tension adjuster, a ratio according to the purpose of improving ejection stability, compatibility with print heads and ink cartridges, storage stability, image storage stability, and other various performances. Resistance adjusting agents, film forming agents, dispersants, surfactants, ultraviolet absorbers, antioxidants, fading inhibitors, antifungal agents, rust inhibitors, and the like can also be added.

  The ink jet recording liquid of the present invention is not particularly limited with respect to the recording method to be used, but can be preferably used as an ink jet recording liquid for an on-demand type ink jet printer. As an on-demand type, an electro-mechanical conversion type (for example, a single cavity type, a double cavity type, a bender type, a piston type, a shear mode type, a shared wall type, etc.), an electro-thermal conversion type (for example, a thermal type) Specific examples include an ink jet type, a bubble jet (registered trademark) type, an electrostatic suction type (for example, an electric field control type, a slit jet type, etc.), and a discharge type (for example, a spark jet type). it can.

  The color toner of the present invention contains at least one kind of metal chelate dye having the dye represented by the general formula (1) or the dye represented by the general formula (2) as a ligand. Yes. The content of the metal chelate dye having the dye represented by the general formula (1) or the dye represented by the general formula (2) as a ligand in the present invention is 2 to 30% by mass in the toner particles. Preferably there is. In addition to the metal chelate dye of the present invention, the color toner is mainly composed of a binder resin, a release agent, a charge control agent, and an external additive.

  As the binder resin for forming the base, all binders generally used for toners can be used. For example, a styrene resin, an acrylic resin, a styrene / acrylic resin, a polyester resin, and the like can be given. Further, external additives such as inorganic fine powder and organic fine particles may be added to the toner for the purpose of improving the fluidity of the toner and controlling charging. As the external additive, silica fine particles and titania fine particles whose surfaces are treated with an alkyl group-containing coupling agent or the like are preferably used. The number average primary particle diameter of these is preferably 10 to 500 nm, and the addition amount thereof is preferably 0.1 to 20% by mass with respect to the toner.

  In addition, as a release agent added to the toner particles for the purpose of improving the heat fixing property, a release agent conventionally used for toners can be used. Specific examples include olefins such as low molecular weight polypropylene, low molecular weight polyethylene, ethylene-propylene copolymer, microcrystalline wax, carnauba wax, sazol wax, and paraffin wax. These addition amounts are preferably 1 to 5% by mass in the toner.

  Further, the charge control agent for improving the charging characteristics may be added as necessary, but is preferably colorless from the viewpoint of color developability, for example, those having a quaternary ammonium salt structure, those having a calixarene structure, etc. Is mentioned.

  When the color toner of the present invention is used for a two-component developer, it is used by mixing with a carrier. As the carrier, either an uncoated carrier composed only of magnetic material particles such as iron and ferrite, or a resin-coated carrier whose magnetic material particle surface is coated with a resin or the like may be used. The average particle size of the carrier is preferably 30 to 150 μm in terms of volume average particle size.

  The image forming method to which the color toner of the present invention is applied is not particularly limited. For example, a method of forming an image by repeatedly forming a color image on a photoconductor to form an image, or a photoconductor Examples include a method in which the formed image is sequentially transferred to an intermediate transfer member or the like, a color image is formed on the intermediate transfer member or the like, and then transferred to an image forming member such as paper to form a color image.

  When the metal chelate dye having the dye represented by the general formula (1) or the dye represented by the general formula (2) as a ligand is used for a color filter, the metal chelate dye is used as a transparent resin. In the case of dispersing in the form, various dispersing means such as a two-roll mill, a three-roll mill, a sand mill, and a kneader can be used.

  In the present invention, as the resin varnish, a varnish used in a conventionally known colored composition for a color filter is used. As the dispersion medium, a solvent or an aqueous medium suitable for the resin varnish is used. If necessary, conventionally known additives such as a dispersion aid, a smoothing agent, and an adhesive agent are added and used.

  As the resin varnish, a photosensitive resin varnish and a non-photosensitive resin varnish are used. Examples of the photosensitive resin varnish are photosensitive resin varnishes used for ultraviolet curable inks, electron beam curable inks, etc., and non-photosensitive resin varnishes include, for example, relief printing inks, planographic inks, intaglio gravure inks, Any of varnishes used for printing inks such as stencil screen inks, varnishes used for electrodeposition coating, varnishes used for developers of electronic printing and electrostatic printing, and varnishes used for thermal transfer ribbons can be used.

  Examples of the photosensitive resin varnish include a photosensitive cyclized rubber resin, a photosensitive phenol resin, a photosensitive polymethacrylate resin, a photosensitive polyamide resin, a photosensitive polyimide resin, and an unsaturated polyester resin. Examples include varnishes such as polyester acrylate resins, polyepoxy acrylate resins, polyurethane acrylate resins, polyether acrylate resins, polyol acrylate resins, and varnishes to which a monomer is added as a reactive diluent. Photopolymerization initiator such as benzoin ether and benzophenone in the metal chelate dye having the dye represented by the general formula (1) or the dye represented by the general formula (2) as a ligand and the varnish of the present invention. In addition, the photosensitive coloring composition according to the present invention can be obtained by bricking by a conventionally known method. Moreover, it can replace with said photoinitiator and can use it as a thermopolymerizable coloring composition using a thermal polymerization initiator. When forming a color filter pattern using the above photosensitive coloring composition, spin coating the photosensitive coloring composition on a transparent substrate, coating the entire surface using a low-speed rotary coater, roll coater, knife coater, etc. Or performing full printing by various printing methods or partial printing slightly larger than the pattern, and after pre-drying, the photomask is brought into close contact, and exposure is performed using an ultrahigh pressure mercury lamp to print the pattern. Subsequently, development and washing are performed, and post-baking is performed as necessary to form a color filter pattern.

  Examples of non-photosensitive resin varnishes include cellulose acetate resins, nitrocellulose resins, styrene (co) polymers, polyvinyl butyral resins, amino alkyd resins, polyester resins, amino resin modified polyester resins Resin, polyurethane resin, acrylic polyol urethane resin, soluble polyamide resin, soluble polyimide resin, soluble polyamideimide resin, soluble polyesterimide resin, casein, hydroxyethyl cellulose, styrene-maleic acid ester copolymer water-soluble Salts, water-soluble salts of (meth) acrylic acid ester (co) polymers, water-soluble aminoalkyd resins, water-soluble aminopolyester resins, water-soluble polyamide resins, and the like. These can be used alone or in combination. The

  When forming a color filter pattern using the above-mentioned non-photosensitive coloring composition, the non-photosensitive coloring composition, for example, the above-described various printing methods using a printing ink for color filters is used on a transparent substrate. A method of printing a colored pattern directly on a substrate, a method of forming a colored pattern on a substrate by electrodeposition coating using an aqueous electrodeposition coating composition for a color filter, an electronic printing method or an electrostatic printing method, or a transfer And a method of once forming a colored pattern on the conductive substrate by the above-mentioned method and the like and transferring it to the color filter substrate. Subsequently, baking is performed as necessary according to a conventional method, polishing for smoothing the surface, or top coating for protecting the surface is performed. Further, a black matrix is formed according to a conventional method to obtain an RGB color filter.

  Next, the optical information recording medium and the optical information recording method of the present invention will be described in detail.

  The substrate constituting the optical information recording medium of the present invention is required to be substantially transparent (transmittance of 80% or more) in the wavelength region (390 to 900 nm) of light used for recording / reproduction. When used as a normal compact disc, the shape of the substrate is about 0.5 to 1.2 mm in thickness and about 80 to 120 mm in diameter. Examples of the material constituting the substrate include polymethyl methacrylate resin, acrylic resin, polycarbonate resin, epoxy resin, polysulfone resin, transparent resin such as methylpentene polymer, and glass. An oxygen barrier film may be formed on the outer surface, inner surface, and inner / outer peripheral surface of the substrate as necessary. Further, it is preferable that a tracking groove is formed on the substrate on which the recording layer is formed.

  The optical information recording medium having a recording layer containing the metal chelate dye of the present invention has both light absorption suitable for recording and reflectance suitable for reproduction. The extinction coefficient k is preferably 0.01 to 0.1. On the other hand, the refractive index n (real part of the complex refractive index) of the recording layer in the wavelength region of the laser light is preferably 1.5 to 4.0.

  The recording layer of the optical information recording medium of the present invention may contain various resins, surfactants, antistatic agents, dispersants, antioxidants, crosslinking agents and the like. In addition, the recording layer may be formed on one surface of the substrate or may be formed on both surfaces of the substrate. The thickness of the recording layer is usually preferably 500 to 3000 angstroms.

  The method for forming the recording layer on the substrate is not particularly limited. For example, the spin coating method, the dip coating method, the spray coating method, the blade coating method, the roller coating method, the bead coating method, the Meyer coating method. Various methods such as a curtain coating method can be applied. Examples of the solvent used for forming the recording layer include ketone solvents such as cyclohexanone, ester solvents such as butyl acetate, ether solvents such as ethyl cellosolve, alcohol solvents such as diacetone alcohol and fluorinated alcohol. And aromatic solvents such as toluene, alkyl halide solvents and the like.

  A reflective layer may be provided on the recording layer. The reflective layer can be formed by means of vapor deposition, sputtering, or the like using a metal with high reflectivity such as Au, Al—Mg alloy, Al—Ni alloy, Ag, Pt, and Cu. The thickness of the reflective layer is preferably 500 angstroms or more. On the reflective layer, a protective film made of, for example, an ultraviolet curable resin may be formed. The thickness of the protective film is about 0.1 to 100 μm, and the hardness is preferably H to 8H in pencil hardness at 25 ° C. An adhesive layer may be provided between the recording layer and the reflective layer to bring them into close contact. The thickness of the adhesive layer is preferably 10 to 300 angstroms.

  Examples of the light source for recording and reproducing the optical information recording medium of the present invention include a solid laser, a gas laser, a dye laser, and a semiconductor laser. Since the metal chelate dye of the present invention has a particularly high recording sensitivity, it is suitable for recording and reproduction using a 635 nm or 650 nm semiconductor laser, a 532 nm YAG harmonic laser, or the like.

  EXAMPLES Next, although an Example demonstrates this invention further in detail, this invention is not limited to a following example.

Example 1
Although the synthesis | combining method of the metal chelate pigment | dye of this invention is shown below, this invention is not limited to this.

  Synthesis of Exemplified Dye 1-1

  After dissolving 21.9 g of compound A in 200 ml of acetone, a solution obtained by dissolving 26 ml of concentrated hydrochloric acid in 160 ml of water was added. After this solution was cooled with ice water, a solution prepared by dissolving 7 g of sodium nitrite in 20 ml of water was slowly added dropwise. The mixture was stirred for 30 minutes to prepare a diazonium salt solution of Compound A.

  After dissolving 17.2 g of compound B and 18.9 g of potassium acetate in 250 ml of methanol, the solution was cooled with ice water. The diazonium salt solution of compound A prepared prior to this was slowly added and stirred as it was for 1 hour. After completion of the reaction, the precipitated solid was filtered and washed successively with water and methanol. The obtained solid was recrystallized from toluene to obtain 32.1 g of a red solid.

When the obtained solid was analyzed by ¹ H-NMR and MASS spectrum, it was confirmed to be Exemplified Dye 1-1. The yield was 80%.

  Synthesis of Exemplary Metal Chelate Dye 2-10

  4.6 g of Exemplified Dye 1-1 was dissolved in 50 ml of methanol, 3.0 g of Exemplified Metal Ion-containing Compound M-14 was added thereto, and reacted for 1 hour under heating and reflux. After completion of the reaction, the solvent was distilled off, and acetonitrile was added for crystallization. The obtained crystals were filtered, washed and dried to obtain the target exemplified metal chelate dye 2-10.

  The spectral absorption spectrum of the metal chelate dye obtained above in an acetone solution was measured, and the maximum absorption wavelength and the maximum molar extinction coefficient of the dye were determined (as per molecule of the dye constituting the metal chelate dye). The maximum absorption wavelength was 532 nm, and the maximum molar extinction coefficient was 63000. Moreover, the following hue evaluation was performed visually. The results are shown below. In addition, the visual hue evaluation result of the comparative metal chelate dye 2-1 and the comparative dye 1-1 described below is also shown for comparison. The hue was visually evaluated as magenta.

○: Hue is the best Δ: Hue is good ×: Hue is poor.

  As shown in Table 1, it was found that the metal chelate dye of the present invention has a large maximum molar extinction coefficient and has a particularly excellent hue as a magenta dye.

Example 2
Exemplified metal chelate dye 2-15 was synthesized in the same manner as in Example 1, and the spectral absorption spectrum was measured. As a result, a high maximum molar extinction coefficient and the best hue were obtained. Further, exemplary metal chelate dye 2-17 was synthesized. When the spectral absorption spectrum was measured, a high maximum molar extinction coefficient and a good hue were obtained.

Example 3
0.2 g of the exemplary metal chelate dye 2-10 obtained in Example 1, 2.0 g of tricresyl phosphate, and 0.16 g of sodium dodecylbenzenesulfonate were dissolved in 1.3 g of ethyl acetate. Next, 6.8 g of a 15% aqueous solution of lime-processed gelatin and 5.5 g of water were added to a homogeneous mixture at 40 ° C., and the mixture was emulsified and dispersed at 40 ° C. and 10,000 rpm for 10 minutes using a homogenizer. A colored composition was prepared as an emulsified dispersion. In the obtained coloring composition, it watered so that the density | concentration of exemplary metal chelate pigment | dye 2-10 might be set to 0.25 mmol / m < ² >, and this was apply | coated using the wire bar on the support body for photographic paper. The film formed after coating exhibited a good magenta color and good light resistance.

Example 4
(Preparation of water-based ink)
Weighed the dyes listed in Table 2 so that the dye content was 2% by weight as the finished ink, ethylene glycol 15%, glycerin 15%, Surfynol 465 (Nisshin Chemical Industry Co., Ltd.) 0.3%, The remainder was dissolved and prepared so as to be pure water, and further filtered through a 2 μm membrane filter to remove dust and coarse particles to obtain ink jet inks 1 to 6.

(Sample preparation and evaluation)
Furthermore, each ink was printed on Konica photo jet paper Photolike QP glossy paper (made by Konica Minolta Co., Ltd.) using a commercially available Epson inkjet printer (PM-800), and the resulting images were evaluated for light resistance and hue. Table 2 shows the results of the above.

  Light resistance: The rate of decrease in reflection spectral density at the maximum absorption wavelength in the visible region from an unexploded sample after 48 hours of xenon light (70000 lux) bombardment using a xenon weather meter manufactured by Suga Test Instruments Co., Ltd. Light resistance (%) = (exposed sample maximum absorption wavelength concentration / unexposed sample maximum absorption wavelength concentration) × 100 was calculated.

  Hue: Hue was evaluated visually as magenta.

○: Best hue and particularly suitable for use as an ink jet recording liquid Δ: Good hue and suitable for use as an ink jet recording liquid ×: Poor hue and practical use as an ink jet recording liquid Top problem.

  As is clear from the above results, it can be seen that the present invention is superior in light resistance and hue as compared with the comparison.

Example 5
(Preparation of colored fine particle dispersion)
Table 3 shows the dye 5 g, 5 g of polyvinyl butyral (manufactured by Sekisui Chemical Co., Ltd. BL-S, average polymerization degree 350) and 50g of ethyl acetate to put in a separable flask, after the inside of the flask N ₂ substitutions, the polymer was stirred And the dye was completely dissolved. After dropping 100 g of an aqueous solution containing 2 g of sodium lauryl sulfate, the mixture was emulsified for 300 seconds using an ultrasonic disperser (UH-150 type, manufactured by SMT Co., Ltd.). Thereafter, ethyl acetate was removed under reduced pressure to obtain colored fine particles impregnated with the dyes shown in Table 3. 0.15 g of potassium persulfate was added to this dispersion and dissolved, and after heating to 70 ° C. with a heater, 7 g of a mixture of 2 g of styrene and 1 g of 2-hydroxyethyl methacrylate was added dropwise. By reacting, a core-shell type colored fine particle dispersion was obtained.

(Preparation of water-based ink)
The above-mentioned colored fine particle dispersion in which the pigment content is 2% by mass with respect to the finished amount of the ink is weighed, ethylene glycol 15% by mass, glycerin 15% by mass, triethylene glycol monobutyl ether 3% by mass, Surfynol. 465 was prepared and mixed so that 0.3% by mass and the remainder was pure water, and further filtered through a 2 μm membrane filter to remove dust and coarse particles, and as shown in Table 3, inkjet inks 11 to 16 were used. Got.

(Sample preparation and evaluation)
Furthermore, each ink was printed on Konica photo jet paper Photolique QP glossy paper (made by Konica Minolta Co., Ltd.) using a commercially available Epson inkjet printer (PM-800), and the light resistance of the obtained images was evaluated. The results are also shown in Table 3.

(Light resistance)
Decrease rate of reflection spectral density at the maximum absorption wavelength in the visible region from an unexploded sample after 48 hours of xenon light (70000 lux) bombardment using a xenon weather meter manufactured by Suga Test Instruments Co., Ltd. ), Light resistance (%) = (exposed sample maximum absorption wavelength concentration / unexposed sample maximum absorption wavelength concentration) × 100 was calculated and evaluated as follows. In each case, the light resistance was 90% or more, light resistance A, 80% or more and less than 90% light resistance B, and less than 80% light resistance C.

(Ink storage stability)
The change rate of the particle diameter when each ink was stored at 60 ° C. for 7 days and the filterability of the ink after storage were evaluated. In addition, this particle diameter is an average particle diameter, and was measured by Malvern Co., Ltd. Zetasizer 1000HS.

  Change rate of particle size: Ink was stored at 60 ° C. for 7 days, when the change rate of particle size was less than 5%, ◎ 5% to less than 10% ○ (acceptable level), 10% or more × (Impossible level).

  Filterability: After storing the ink at 60 ° C. for 7 days, 5 ml of the ink was collected and filtered through a 0.8 μm cellulose acetate membrane filter. ), And those that could not be filtered by more than half were marked as x (impossible level).

  As is clear from the above results, it can be seen that the ink of the present invention is superior in light resistance, further the particle diameter change rate, and the filterability as compared with the comparison, in terms of storage stability as an ink.

Example 6
<Manufacture of color toner: grinding method>
100 parts by mass of a polyester resin, 8 parts by mass of a dye (colorant) described in Table 4 and 3 parts by mass of polypropylene were mixed, kneaded, pulverized and classified to obtain a powder having a volume average particle size of 8.5 μm. Further, 100 parts by mass of this powder and 1.0 part by mass of silica fine particles (number average primary particle size 12 nm) were mixed with a Henschel mixer (manufactured by Mitsui Miike Chemical Co., Ltd.) to obtain color toners 1 to 5 by a pulverization method.

<Manufacture of color toner: polymerization method>
In an aqueous solution in which 5 g of sodium dodecyl sulfate was dissolved in 200 ml of pure water, 20 g of the dye (colorant) described in Table 4 was added, and stirring and ultrasonic waves were applied to create an aqueous dispersion of the colorant. An emulsion dispersion prepared by emulsifying the aqueous dispersion and low molecular weight polypropylene (number average molecular weight = 3200) in water so as to have a solid content concentration of 30% by mass with a surfactant was prepared in advance.

  60 g of low molecular weight polypropylene emulsified dispersion is mixed with the above dispersion of the colorant, 220 g of styrene monomer, 40 g of n-butyl acrylate monomer, 12 g of methacrylic acid monomer, 5.4 g of t-dodecyl mercaptan as a chain transfer agent After adding 2000 ml of pure water, emulsion polymerization was carried out by maintaining at 70 ° C. for 3 hours while stirring under a nitrogen stream.

  To 1000 ml of the resulting dispersion of the colorant-containing resin fine particles, sodium hydroxide was added to adjust the pH to 7.0, 270 ml of a 2.7 mol% aqueous potassium chloride solution was added, 160 ml of isopropyl alcohol, and 9.0 g of polyoxyethylene octylphenyl ether having an average degree of polymerization of ethylene oxide of 10 was dissolved in 67 ml of pure water and added, and the reaction was carried out with stirring at 75 ° C. for 6 hours.

  The obtained reaction solution is filtered, washed with water, further dried and pulverized to obtain colored particles, and 1.0 part by mass of the colored particles and silica fine particles (number average primary particle size: 12 nm) is combined with a Henschel mixer (Mitsui Miike Chemical Industries). And color toners 6 to 10 were obtained by polymerization.

<Manufacture of developer>
To 10 parts by mass of these color toners, 900 parts by mass of carrier iron powder “EFV250 / 400” (manufactured by Nippon Iron Powder) was uniformly mixed to obtain a “developer”.

<Evaluation equipment>
The above color toner and developer are set in the developing unit of a commercially available color image forming apparatus “Konica 9331” (manufactured by Konica Minolta Business Technologies Co., Ltd.) adopting an electrophotographic method, printing is performed, and the following evaluation items are evaluated. went. In order to clarify the difference in color toner performance, the evaluation was made by modifying the color toner so that it can be used in all four color developing units. The evaluation sample produced the reflection image (image on paper) and the transmission image (OHP image) on paper and OHP, respectively. The color toner was prepared in an amount of 0.65 to 0.75 mg / cm ² . About each obtained image sample, the hue, light fastness, and transparency of an OHP image were evaluated as follows.

《Hue》
The hue was visually evaluated as magenta.

○: Best hue and particularly suitable for use as a color toner Δ: Good hue and suitable for use as a color toner ×: Poor hue and practical problems for use as a color toner

《Light resistance》
The light resistance was evaluated based on the residual dye ratio determined from the difference in image density before and after the xenon light irradiation. For the dye residual ratio, after measuring the color toner image density Ci immediately after image formation, a weather meter “Atlas C.165” (manufactured by Atlas) was used to apply 5 xenon light (85,000 lux) to the color toner image. After irradiation for a day, the color toner image density Cf was measured again, and the residual dye ratio ({(Ci−Cf) / Ci} × 100%) was calculated from the difference in image density before and after the xenon light irradiation. The image density was measured using a reflection densitometer “X-rite 310TR” (manufactured by X-rite Company).

○: Dye remaining ratio is 90% or more and excellent in light resistance. Δ: Dye remaining ratio is 80 to 89%, light resistance is good, and there is no practical problem. ×: Dye remaining ratio is less than 80% and light resistance is improved. Inferior practical problem.

<Transparency of OHP image>
The transparency of the OHP image was evaluated with a spectral transmittance of 650 nm.
Spectral transmittance was determined by measuring the visible spectral transmittance of a color toner image using a “330-type self-recording spectrophotometer” (manufactured by Hitachi, Ltd.), using an OHP sheet on which no color toner is supported as a reference, at 650 nm. Spectral transmittance was determined.

○: Spectral transmittance is 80% or more and transparency is very good and good Δ: Spectral transmittance is 70 to 80% and transparency is good and no practical problem ×: Spectral transmittance is 70% or less and transparency is poor Practical problem.

  Table 4 shows the evaluation results of hue, light fastness, and transparency of the OHP image.

  As is apparent from Table 4, an image produced using the color toner of the present invention exhibits particularly good hue and high OHP quality, and the color toner of the present invention is suitable for use as a full-color magenta toner. Furthermore, since an image produced using the color toner of the present invention has good light resistance, it can be stored for a long period of time.

Example 7
<Preparation of photosensitive coating agent for color filter>
In order to obtain an RGB color filter, a mosaic pattern was formed on the glass plate by the following method. A photosensitive coating agent for a color filter was prepared using the components shown below. The used photosensitive polyimide resin varnish is a photosensitive polyimide resin varnish containing a photosensitizer.

<Photosensitive coating component for color filter>
<CF-1>
Illustrative metal chelate dye 2-10 10 parts Photosensitive polyimide resin varnish 50 parts N-methyl-2-pyrrolidone 40 parts A glass plate treated with a silane coupling agent is set on a spin coater, and the above CF-1 color filter The photosensitive coating agent was spin-coated at 300 rpm for 5 seconds and then at 2000 rpm for 5 seconds. Next, prebaking was performed at 80 ° C. for 15 minutes, a photomask having a mosaic pattern was brought into close contact, and exposure was performed using an ultrahigh pressure mercury lamp at a light amount of 900 mJ / cm ² . Next, development and washing were performed with a dedicated developer and a dedicated rinse to form a yellow mosaic pattern on the glass plate.

  The color filter obtained above has excellent spectral absorption characteristics, excellent fastness such as light resistance and heat resistance, and also has excellent properties of light transmission, as a color filter for liquid crystal color display It had excellent properties.

  On the other hand, a comparative color filter was produced in the same manner except that the following comparative dye 1-8 was used instead of the exemplified metal chelate dye 2-10, but the light resistance and heat resistance were excellent at the same level, but Absorption characteristics and light transmission were inferior, and it was not suitable as a color filter.

Example 8
<Optical information recording medium>
(A) Manufacture of optical information recording medium 1 A recording layer is coated on a polycarbonate substrate with a groove having a diameter of 5 inches using the exemplified metal chelate dye 2-17 according to the present invention, and a reflective layer (Au, thickness 1000 mm) Then, a protective film (ultraviolet curable resin, thickness 5 μm) was sequentially formed according to a conventional method to produce the optical information recording medium 1 of the present invention.

(B) Manufacture of optical information recording medium 2 The present invention is the same except that the exemplified metal chelate dye 2-43 according to the present invention is used instead of the exemplified metal chelate dye 2-17 used in the optical information recording medium 1. The optical information recording medium 2 was manufactured.

(C) Production of optical information recording medium 3 for comparison Comparative optical information in the same manner except that comparative metal chelate dye 2-7 was used instead of exemplified metal chelate dye 2-17 used in the optical information recording medium. Recording medium 3 was manufactured.

  When the reflectance of the optical information recording medium produced above was measured, all of the optical information recording medium 1, the optical information recording medium 2, and the optical information recording medium 3 showed 70% or more. Information was recorded on these samples by changing the power with a 633 nm semiconductor laser, and reproduction was performed at 0.8 mW. Further, the same recording / reproducing experiment was performed after light irradiation of 70,000 lux and 30 hours using a xenon fade meter. Table 5 shows the minimum recording power and the number of reproductions before and after the light exposure.

  As is apparent from Table 5, the optical information recording medium 1 and the optical information recording medium 2 of the present invention were able to perform good recording and reproduction satisfying the DVD standard, and in particular, stable recording excellent in light resistance. -It became clear that it has reproduction characteristics.

  The same results were obtained even when the exemplified metal chelate dye 2-20 and the exemplified metal chelate dye 2-47 of the present invention were used in place of the exemplified metal chelate dyes 2-17 and 2-43 of the present invention described in Table 5. Got.

  On the other hand, the optical information recording medium 3 for comparison showed a phenomenon in which the reflectance was lowered by the reproduction light of the laser, causing reproduction failure, and recording was impossible even by light irradiation with a xenon fade meter.

Claims (9)

The coloring composition characterized by containing the metal chelate pigment | dye which makes the pigment | dye represented by following General formula (1) a ligand.
(In the formula, R ₁ represents a hydrogen atom or a substituent, R ₂ represents a substituent, n represents an integer of 0 to 3, and when n is 2 or more, a plurality of R ₂ may be the same) G represents a chelatable group, A represents an aryl group or a heterocyclic group, and X forms a 5- to 6-membered nitrogen-containing heterocyclic ring together with the —N—C—N— moiety. Represents a group of non-metallic atoms necessary for The coloring composition according to claim 1, wherein the coloring matter represented by the general formula (1) is represented by the following general formula (2).
_{(Wherein, R 1, R 2, n} , R 1 in the G and A are the general formula _{(1), R 2, n} , .R 3 is synonymous with G and A represents a hydrogen atom or a substituent. ) A metal chelate dye having the dye represented by the general formula (1) in the colored composition according to claim 1 or the dye represented by the general formula (2) in the colored composition according to claim 2 as a ligand. An ink jet recording liquid comprising at least one of the following. An ink jet recording method comprising: spraying the ink jet recording liquid according to claim 3 on a recording medium for recording. A metal chelate dye having the dye represented by the general formula (1) in the colored composition according to claim 1 or the dye represented by the general formula (2) in the colored composition according to claim 2 as a ligand. A color toner comprising at least one of the following. A metal chelate dye having the dye represented by the general formula (1) in the colored composition according to claim 1 or the dye represented by the general formula (2) in the colored composition according to claim 2 as a ligand. A color filter comprising at least one of the following. A metal chelate dye having the dye represented by the general formula (1) in the colored composition according to claim 1 or the dye represented by the general formula (2) in the colored composition according to claim 2 as a ligand. An optical information recording medium comprising a recording layer containing at least one of the following. 8. An optical information recording method comprising recording information by irradiating the optical information recording medium according to claim 7 with a laser beam selected from a range of 390 to 900 nm. A metal chelate dye having the dye represented by the general formula (1) in the colored composition according to claim 1 or the dye represented by the general formula (2) in the colored composition according to claim 2 as a ligand. .