JP2007231242A - Naphthalocyanine dye compound - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new naphthalocyanine dye in relation to a naphthalocyanine dye compound useful as an image-forming material, an infrared heat-sensitive type recording material, an optical recording device and an optical film material, etc. <P>SOLUTION: The compound is represented by general formula (A) (wherein, Ar represents an aromatic group; and * represents a monovalent negative charge or a direct bond). <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a naphthalocyanine dye compound useful as an image forming material, an infrared thermosensitive recording material, an optical recording element and an optical film material, and more particularly to a novel naphthalocyanine dye having excellent absorption characteristics. is there.

  Phthalocyanines have been widely used as pigments. Among them, naphthalocyanine dyes do not substantially absorb visible light, but have been actively studied as near-infrared dyes that absorb infrared rays (for example, Patent Document 1). .

Many of the substituted naphthalocyanines known so far have a substituent on the naphthalene ring. The naphthalocyanine dye having a substituent on the naphthalene ring includes a halogen atom, a carbon bond type (for example, an alkyl group, an aryl group), an oxygen bond type (for example, a hydroxyl group, an alkoxy group, an aryloxy group), and a sulfur bond. Type (for example, alkylthio group, arylthio group), nitrogen bond type (for example, amino group, alkylamino group), carbonyl bond type (for example, oxycarbonyl group, alkoxycarbonyl group), and nitrile group, nitro group (for example, Patent Document 1) Non-Patent Document 1), those having an acrylamide group as a polymerization precursor (for example, Patent Document 2), those having an acylamino group and its precursor (for example, Patent Documents 3 to 5), and the like have been known. A structure having a substituent in a portion other than the naphthalene ring has not been known so far, and its new physical properties have been expected.
Japanese Patent Laid-Open No. 2-29685 JP-A-7-118723 Japanese Patent Laid-Open No. 11-152413 Japanese Patent Laid-Open No. 11-152414 Japanese Patent Laid-Open No. 11-152415 Journal of Chemical Society, Perkin Transaction, I, pp. 2453-2458 (1988)

  An object of the present invention is to provide a novel naphthalocyanine dye compound useful as an image forming material, an infrared thermosensitive recording material, an optical recording element, an optical film material, and the like, and to provide a dye using the same. .

As a result of intensive studies, the present inventors have found that the above object of the present invention can be achieved by the following means.
(1) A compound represented by the following general formula (A).

In general formula (A), Ar represents an aromatic group, the bond of Ar is bonded to any oxygen atom or nitrogen atom of the naphthalocyanine compound, and the bonded nitrogen atom is a monovalent cation. * Represents a monovalent negative charge or a bond.
(2) The compound according to (1), wherein the compound represented by the general formula (A) is a compound represented by the following general formula (1).

In the general formula (1), two 1-naphthoxy groups may be located on the same side or opposite sides of the plane of the naphthalocyanine ring, or may be a mixture thereof. Good.
(3) The compound according to (1), wherein the compound represented by the general formula (A) is a compound represented by the following formula (A1).

In general formula (A1), the 1-naphthyl group is bonded to any nitrogen atom of the naphthalocyanine compound, and the bonded nitrogen atom is a monovalent cation.
(4) The compound according to (3), wherein the compound represented by the general formula (A1) is a compound represented by the following general formula (2).

In the general formula (2), the two 1-naphthyl groups may be located on the same side or opposite sides of the plane of the naphthalocyanine ring, or may be a mixture thereof. Good.
(5) A phthalocyanine dye comprising the compound according to any one of (1) to (4).

  According to the present invention, it is possible to provide a novel naphthalocyanine compound useful as an image forming material, an infrared thermosensitive recording material, an optical recording element, an optical film material, and the like, and a dye using the same. The phthalocyanine compound of the present invention has an absorption maximum at 800 to 850 nm.

Hereinafter, embodiments of the present invention will be described in detail.
First, the compound represented by formula (A) will be described.
In the general formula (A), Ar is bonded to an oxygen atom or a nitrogen atom of the vanadyl naphthalocyanine skeleton. Here, two Ar atoms may be bonded to two oxygen atoms or two nitrogen atoms, or one may be bonded to an oxygen atom and the other bonded to a nitrogen atom. An aromatic group means an aryl group and a substituted aryl group. These aromatic groups may be condensed with an aliphatic ring, another aromatic ring or a heterocyclic ring. The number of carbon atoms in the aromatic group is preferably 6 to 40, more preferably 6 to 30, and still more preferably 6 to 20. Among them, the aryl group is preferably phenyl or naphthyl, more preferably naphthyl, and particularly preferably 1-naphthyl.

  The aryl part of the substituted aryl group is the same as the above aryl group. Examples of the substituent of the substituted aryl group include a halogen atom (for example, a chlorine atom, a bromine atom, and an iodine atom), an alkyl group [a linear, branched, or cyclic substituted or unsubstituted alkyl group. They are alkyl groups (preferably alkyl groups having 1 to 30 carbon atoms such as methyl, ethyl, n-propyl, isopropyl, t-butyl, n-octyl, eicosyl, 2-chloroethyl, 2-cyanoethyl, 2-ethylhexyl). A cycloalkyl group (preferably a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, such as cyclohexyl, cyclopentyl, 4-n-dodecylcyclohexyl), a bicycloalkyl group (preferably having 5 to 30 carbon atoms). A substituted or unsubstituted bicycloalkyl group, that is, a monovalent group obtained by removing one hydrogen atom from a bicycloalkane having 5 to 30 carbon atoms, for example, bicyclo [1,2,2] heptan-2-yl, bicyclo [2,2,2] octane-3-yl), a tricyclo structure with more ring structures Domo is intended to cover. An alkyl group (for example, an alkyl group of an alkylthio group) in the substituents described below also represents such an alkyl group. ], An alkenyl group [represents a linear, branched or cyclic substituted or unsubstituted alkenyl group. They are alkenyl groups (preferably substituted or unsubstituted alkenyl groups having 2 to 30 carbon atoms, such as vinyl, allyl, prenyl, geranyl, oleyl), cycloalkenyl groups (preferably substituted or substituted groups having 3 to 30 carbon atoms). An unsubstituted cycloalkenyl group, that is, a monovalent group obtained by removing one hydrogen atom of a cycloalkene having 3 to 30 carbon atoms (for example, 2-cyclopenten-1-yl, 2-cyclohexen-1-yl), Bicycloalkenyl group (a substituted or unsubstituted bicycloalkenyl group, preferably a substituted or unsubstituted bicycloalkenyl group having 5 to 30 carbon atoms, that is, a monovalent group obtained by removing one hydrogen atom of a bicycloalkene having one double bond. It is a group.

  For example, bicyclo [2,2,1] hept-2-en-1-yl, bicyclo [2,2,2] oct-2-en-4-yl) are included. An alkynyl group (preferably a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, such as ethynyl, propargyl, trimethylsilylethynyl group), an aryl group (preferably a substituted or unsubstituted aryl having 6 to 30 carbon atoms) Groups such as phenyl, p-tolyl, naphthyl, m-chlorophenyl, o-hexadecanoylaminophenyl), heterocyclic groups (preferably 5- or 6-membered substituted or unsubstituted aromatic or non-aromatic heterocycles A monovalent group obtained by removing one hydrogen atom from a compound, more preferably a 5- or 6-membered aromatic heterocyclic group having 3 to 30 carbon atoms, such as 2-furyl, 2-thienyl, 2-pyrimidinyl, 2-benzothiazolyl), cyano group, hydroxyl group, nitro group, carboxyl group, alkoxy (Preferably, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms such as methoxy, ethoxy, isopropoxy, t-butoxy, n-octyloxy, 2-methoxyethoxy), aryloxy group (preferably carbon A substituted or unsubstituted aryloxy group of formula 6 to 30, for example, phenoxy, 2-methylphenoxy, 4-t-butylphenoxy, 3-nitrophenoxy, 2-tetradecanoylaminophenoxy), silyloxy group (preferably, A silyloxy group having 3 to 20 carbon atoms, such as trimethylsilyloxy, t-butyldimethylsilyloxy),

A heterocyclic oxy group (preferably a substituted or unsubstituted heterocyclic oxy group having 2 to 30 carbon atoms, 1-phenyltetrazol-5-oxy, 2-tetrahydropyranyloxy), an acyloxy group (preferably a formyloxy group, A substituted or unsubstituted alkylcarbonyloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted arylcarbonyloxy group having 6 to 30 carbon atoms, such as formyloxy, acetyloxy, pivaloyloxy, stearoyloxy, benzoyloxy, p- Methoxyphenylcarbonyloxy), a carbamoyloxy group (preferably a substituted or unsubstituted carbamoyloxy group having 1 to 30 carbon atoms, such as N, N-dimethylcarbamoyloxy, N, N-diethylcarbamoyloxy, morpholinocarbonyloxy) N, N-di-n-octylaminocarbonyloxy, Nn-octylcarbamoyloxy), an alkoxycarbonyloxy group (preferably a substituted or unsubstituted alkoxycarbonyloxy group having 2 to 30 carbon atoms, such as methoxycarbonyl Oxy, ethoxycarbonyloxy, t-butoxycarbonyloxy, n-octylcarbonyloxy),

Aryloxycarbonyloxy group (preferably a substituted or unsubstituted aryloxycarbonyloxy group having 7 to 30 carbon atoms such as phenoxycarbonyloxy, p-methoxyphenoxycarbonyloxy, pn-hexadecyloxyphenoxycarbonyloxy) An amino group (preferably an amino group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted anilino group having 6 to 30 carbon atoms, such as amino, methylamino, dimethylamino, anilino N-methyl-anilino, diphenylamino), acylamino group (preferably formylamino group, substituted or unsubstituted alkylcarbonylamino group having 1 to 30 carbon atoms, substituted or unsubstituted arylcarbonyl group having 6 to 30 carbon atoms) Amino group, eg For example, formylamino, acetylamino, pivaloylamino, lauroylamino, benzoylamino, 3,4,5-tri-n-octyloxyphenylcarbonylamino), an aminocarbonylamino group (preferably a substituted or unsubstituted group having 1 to 30 carbon atoms) Substituted aminocarbonylamino, for example, carbamoylamino, N, N-dimethylaminocarbonylamino, N, N-diethylaminocarbonylamino, morpholinocarbonylamino), alkoxycarbonylamino group (preferably substituted or unsubstituted having 2 to 30 carbon atoms) Alkoxycarbonylamino group, for example, methoxycarbonylamino, ethoxycarbonylamino, t-butoxycarbonylamino, n-octadecyloxycarbonylamino, N-methyl-methoxycarbonylamino An aryloxycarbonylamino group (preferably a substituted or unsubstituted aryloxycarbonylamino group having 7 to 30 carbon atoms, such as phenoxycarbonylamino, p-chlorophenoxycarbonylamino, mn-octyloxyphenoxycarbonylamino) ,

Sulfamoylamino group (preferably a substituted or unsubstituted sulfamoylamino group having 0 to 30 carbon atoms, such as sulfamoylamino, N, N-dimethylaminosulfonylamino, Nn-octylaminosulfonylamino ), Alkyl and arylsulfonylamino groups (preferably substituted or unsubstituted alkylsulfonylamino having 1 to 30 carbon atoms, substituted or unsubstituted arylsulfonylamino having 6 to 30 carbon atoms, such as methylsulfonylamino, butylsulfonylamino) , Phenylsulfonylamino, 2,3,5-trichlorophenylsulfonylamino, p-methylphenylsulfonylamino), mercapto group, alkylthio group (preferably a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms such as methylthio , Ethylthio, n-hexadecylthio), arylthio group (preferably substituted or unsubstituted arylthio having 6 to 30 carbon atoms, such as phenylthio, p-chlorophenylthio, m-methoxyphenylthio), heterocyclic thio group (preferably carbon A substituted or unsubstituted heterocyclic thio group having a number of 2 to 30, for example, 2-benzothiazolylthio, 1-phenyltetrazol-5-ylthio), a sulfamoyl group (preferably a substituted or unsubstituted group having 0 to 30 carbon atoms) Sulfamoyl groups such as N-ethylsulfamoyl, N- (3-dodecyloxypropyl) sulfamoyl, N, N-dimethylsulfamoyl, N-acetylsulfamoyl, N-benzoylsulfamoyl, N- (N '-Phenylcarbamoyl) sulfamoyl),

A sulfo group, an alkyl or arylsulfinyl group (preferably a substituted or unsubstituted alkylsulfinyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsulfinyl group having 6 to 30 carbon atoms, such as methylsulfinyl, ethylsulfinyl, phenylsulfinyl; P-methylphenylsulfinyl), an alkyl or arylsulfonyl group (preferably a substituted or unsubstituted alkylsulfonyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsulfonyl group having 6 to 30 carbon atoms, such as methylsulfonyl, Ethylsulfonyl, phenylsulfonyl, p-methylphenylsulfonyl), acyl group (preferably formyl group, substituted or unsubstituted alkylcarbonyl group having 2 to 30 carbon atoms, substituted or unsubstituted aryl group having 7 to 30 carbon atoms). Carbonyl group, heterocyclic carbonyl group bonded to a carbonyl group with a substituted or unsubstituted carbon atom having 4 to 30 carbon atoms, such as acetyl, pivaloyl, 2-chloroacetyl, stearoyl, benzoyl, pn-octyloxy Phenylcarbonyl, 2-pyridylcarbonyl, 2-furylcarbonyl), an aryloxycarbonyl group (preferably a substituted or unsubstituted aryloxycarbonyl group having 7 to 30 carbon atoms, such as phenoxycarbonyl, o-chlorophenoxycarbonyl, m -Nitrophenoxycarbonyl, pt-butylphenoxycarbonyl), an alkoxycarbonyl group (preferably a substituted or unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, such as methoxycarbonyl, ethoxycarbonyl, t Butoxycarbonyl, n- octadecyloxycarbonyl),

A carbamoyl group (preferably a substituted or unsubstituted carbamoyl having 1 to 30 carbon atoms such as carbamoyl, N-methylcarbamoyl, N, N-dimethylcarbamoyl, N, N-di-n-octylcarbamoyl, N- (methyl Sulfonyl) carbamoyl), aryl or heterocyclic azo groups (preferably substituted or unsubstituted arylazo groups having 6 to 30 carbon atoms, substituted or unsubstituted heterocyclic azo groups having 3 to 30 carbon atoms, such as phenylazo, p- Chlorophenylazo, 5-ethylthio-1,3,4-thiadiazol-2-ylazo), imide group (preferably N-succinimide, N-phthalimide), phosphino group (preferably substituted or non-substituted having 2 to 30 carbon atoms) Substituted phosphino groups such as dimethylphosphino, diphenyl Phosphino, methylphenoxyphosphino), phosphinyl group (preferably a substituted or unsubstituted phosphinyl group having 2 to 30 carbon atoms, such as phosphinyl, dioctyloxyphosphinyl, diethoxyphosphinyl), phosphinyloxy group (Preferably a substituted or unsubstituted phosphinyloxy group having 2 to 30 carbon atoms, such as diphenoxyphosphinyloxy, dioctyloxyphosphinyloxy), phosphinylamino group (preferably having 2 carbon atoms) To 30 substituted or unsubstituted phosphinylamino groups such as dimethoxyphosphinylamino, dimethylaminophosphinylamino), silyl groups (preferably substituted or unsubstituted silyl groups having 3 to 30 carbon atoms, For example, trimethylsilyl, t-butyldimethylsilyl, It represents the E nil dimethylsilyl).

  Among the above functional groups, those having a hydrogen atom may be substituted with the above groups by removing this. Examples of such functional groups include an alkylcarbonylaminosulfonyl group, an arylcarbonylaminosulfonyl group, an alkylsulfonylaminocarbonyl group, and an arylsulfonylaminocarbonyl group. Examples thereof include methylsulfonylaminocarbonyl, p-methylphenylsulfonylaminocarbonyl, acetylaminosulfonyl, and benzoylaminosulfonyl.

Preferred substituents for the group represented by Ar include a halogen atom, alkyl group, alkenyl group, alkynyl group, aryl group, heterocyclic group, cyano group, hydroxyl group, nitro group, carboxyl group, alkoxy group, aryloxy group, Silyloxy group, heterocyclic oxy group, acyloxy group, carbamoyloxy group, alkoxycarbonyloxy group, aryloxycarbonyloxy group, amino group, acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfa Moylamino group, alkyl or arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, sulfo group, alkyl or arylsulfinyl group, alkyl Is an arylsulfonyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group, carbamoyl group, imide group, phosphino group, phosphinyl group, phosphinyloxy group, phosphinylamino group, silyl group, more preferably halogen Atom, alkyl group, aryl group, heterocyclic group, cyano group, hydroxyl group, alkoxy group, aryloxy group, silyloxy group, heterocyclic oxy group, acyloxy group, carbamoyloxy group, amino group, acylamino group, alkylthio group, arylthio Group, a heterocyclic thio group, an alkoxycarbonyl group, a carbamoyl group, and an imide group, more preferably a halogen atom, an alkyl group, an aryl group, a heterocyclic group, and an amino group, and more preferably an alkyl group, an aryl group, and a hetero group. It is a cyclic group.
In the present invention, unsubstituted is most preferred.

  Of the compounds represented by the general formula (A), the compound represented by the general formula (1) or the compound represented by the general formula (A1) is preferable.

In the compound represented by the general formula (1), two 1-naphthyloxy groups may be on the same side or opposite sides with respect to the plane of the phthalocyanine ring (dye plane), and a mixture thereof. It may be. In the present invention, it is preferred that the 1-naphthyloxy groups are on opposite sides of the dye plane.
In the compound represented by the general formula (A1), the two 1-naphthyl groups may be bonded to any of the eight nitrogen atoms, but are preferably bonded to different nitrogen atoms.
In the compound represented by the general formula (A1), two 1-naphthyl groups may be on the same side or on the opposite side with respect to the plane (dye plane) of the phthalocyanine ring. There may be. In the present invention, it is preferred that the 1-naphthyl groups are on opposite sides of the dye plane.
Of the compounds represented by the general formula (A1), the compound represented by the general formula (2) is more preferable.

The method for producing the compound represented by the general formula (A) will be described below.
In order to synthesize the compound represented by the general formula (A), the corresponding 2,3-naphthalenedicarboxylic acid or a derivative thereof (an acid anhydride, diamide, dinitrile, etc.) and a compound having an Ar group (for example, halide, hydroxy) Compounds) and vanadium compounds.

  The most preferred vanadium compounds include vanadium (III) chloride, vanadium oxychloride (V), vanadium (III) acetylacetonate and vanadyl (IV) acetylacetonate.

The ratio of these raw materials used in the reaction is preferably from 1.5 to 200 mol, preferably from 2 to 50 mol, per 1 mol of 2,3-naphthalenedicarboxylic acid derivative. More preferably, it is 4-30 mol. Similarly, the amount of the vanadium compound is preferably 0.01 to 10 mol, more preferably 0.1 to 5 mol, still more preferably 0.15 to 2 mol, and still more preferably 0.2 to 1 mol, more preferably 0.22 to 0.4 mol.
In this reaction, it is also preferable to react by adding urea, and the preferable amount of urea added at this time is 0.5 to 10 mol, more preferably 1 to 6 mol, and further preferably 2 to 4 mol. The whole amount may be added at the start or may be added in portions as the reaction proceeds.

Except when a raw material other than nitrile is used as the 2,3-naphthalenedicarboxylic acid derivative, it is preferable to add urea to the reaction, and the preferred amount is 0. 1 to 200 mol, preferably 1 to 100 mol, more preferably 5 to 70 mol.
Further, a method of adding a Lewis acid is also preferable, and a preferable Lewis acid includes a metal ammonium salt. The amount of Lewis acid used is preferably from 0.00001 to 10 mol, more preferably from 0.0001 to 1 mol, still more preferably from 0.001 to 0.5 mol, based on 1 mol of 2,3-naphthalenedicarboxylic acid derivative. Mol, more preferably 0.005 to 0.2 mol, particularly preferably 0.01 to 0.1 mol.

The reaction may be carried out with the above compounds alone or in combination with a solvent.
Examples of the solvent include amide solvents (for example, N, N-dimethylformamide, N, N-dimethylacetamide, 1-methyl-2-pyrrolidone), sulfone solvents (for example, sulfolane) sulfoxide solvents (for example, dimethyl sulfoxide), ether-based solvents. Solvents (eg, dioxane, cyclopentyl methyl ether), ketone solvents (eg, acetone, cyclohexanone), hydrocarbon solvents (eg, toluene, xylene), halogen solvents (eg, tetrachloroethane), alcohol solvents (eg, 1-butanol, ethylene) Glycol, cyclohexanol) and pyridine solvents (for example, pyridine, γ-picoline, 2,6-lutidine) are used alone or in combination. Preferred are amide solvents, sulfone solvents, ether solvents, halogen solvents, alcohol solvents, pyridine solvents, and more preferred are amide solvents, sulfone solvents, ether solvents, halogen solvents, alcohol solvents. More preferred are amide solvents and alcohol solvents, and more preferred solvents are amide solvents.

  The reaction temperature is preferably 0 to 250 ° C., more preferably 50 to 250 ° C., still more preferably 80 to 230 ° C., particularly preferably 150 to 220 ° C., and the reaction temperature may be changed during the reaction. (For example, the first half 150 ° C. and the second half 200 ° C.) are also preferable, and the reaction time is preferably 5 minutes to 30 hours.

During the reaction, it is also preferable to remove by-product water out of the system, a method in which it is distilled off under reduced pressure or normal pressure alone or with a solvent, a method using an absorbent such as molecular sieve, a dehydrating condensing agent such as acetic anhydride. The method of using is preferably used.
In addition, this reaction is also preferably performed in a closed system.

  The present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto.

Example 1
Based on the following reaction, the compound (1) of the present invention was synthesized.

In a three-necked flask, 5.49 g of compound (a), 7.2 g of urea, 0.1 g of ammonium molybdate, 0.87 g of VOCl ₃ and 20 g of chloronaphthalene were added and stirred at room temperature for 10 minutes. The mixture was stirred for 1 hour at ˜146 ° C., further stirred for 1 hour at an internal temperature of 191 to 195 ° C., and further stirred for 5 hours at an internal temperature of 239 to 244 ° C. Then, the internal temperature was cooled to 50 ° C., 50 ml of chloroform was added and stirred for 30 minutes, and the filtrate obtained by filtration was concentrated by a rotary evaporator. The residue thus obtained was purified by silica gel column chromatography to obtain 1.6 g of the desired compound (1) (yield 30%).
Mass spectrum result: (M + H) ⁺ = 1354.3321
(Reference: Calculated value = 13544.3893)
Melting point: 300 ° C. or higher The absorption spectrum of this compound showed an absorption maximum at 832 nm in a THF solvent.

(Example 2)
Based on the following reaction, the compound (2) of the present invention was synthesized.

In a three-necked flask, 5.49 g of compound (a), 7.2 g of urea, 0.1 g of ammonium molybdate, 0.87 g of VOCl ₃ and 20 g of chloronaphthalene were added and stirred at room temperature for 10 minutes. The mixture was stirred for 1 hour at ˜146 ° C., further stirred for 1 hour at an internal temperature of 191 to 195 ° C., and further stirred for 5 hours at an internal temperature of 239 to 244 ° C. Then, the internal temperature was cooled to 50 ° C., 50 ml of chloroform was added and stirred for 30 minutes, and the filtrate obtained by filtration was concentrated by a rotary evaporator. The residue thus obtained was purified by silica gel column chromatography to obtain 1.6 g of the desired compound (2) (yield 30%).
Mass spectrum result: (M + H) ⁺ = 1354.3321
(Reference: Calculated value = 13544.3893
Melting point: 300 ° C. or higher The absorption spectrum of this compound showed an absorption maximum at 832 nm in a THF solvent.

Claims (5)

The compound represented by the following general formula (A).

In general formula (A), Ar represents an aromatic group, the bond of Ar is bonded to any oxygen atom or nitrogen atom of the naphthalocyanine compound, and the bonded nitrogen atom is a monovalent cation. * Represents a monovalent negative charge or a bond. 2. The compound according to claim 1, wherein the compound represented by the general formula (A) is a compound represented by the following general formula (1).

In the general formula (1), two 1-naphthoxy groups may be located on the same side or opposite sides of the plane of the naphthalocyanine ring, or may be a mixture thereof. Good. 2. The compound according to claim 1, wherein the compound represented by the general formula (A) is a compound represented by the following formula (A1).

In general formula (A1), the 1-naphthyl group is bonded to any nitrogen atom of the naphthalocyanine compound, and the bonded nitrogen atom is a monovalent cation. 4. The compound according to claim 3, wherein the compound represented by the general formula (A1) is a compound represented by the following general formula (2).

In the general formula (2), the two 1-naphthyl groups may be located on the same side or opposite sides of the plane of the naphthalocyanine ring, or may be a mixture thereof. Good. A phthalocyanine dye comprising the compound according to any one of claims 1 to 4.