JPH11302551A - Dipyrromethene metal chelate compound and photorecording medium containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound recordable and reproducible at a short wavelength and useful as a recording layer of an additional recording type high density photorecording medium, having a specific dipyrromethene-based compound as a ligand. SOLUTION: This chelate compound is composed of (A) a compound of formula I [R1 to R5 are each H, a halogen, an amino, a 1-20C alkyl or the like; A is a (substituted) heterocyclic ring or a (substituted) naphthalene ring] and (B) a metal ion, e.g. bis[(1-phenyl-4-azaisoindol-3-yl) (3,5-diphenylpyrrol-2,2- diyl)methene]copper. The chelate compound is obtained by, e.g. reacting a compound of formula II with a compound of formula II to obtain the compound of formula I and reacting the resultant compound with an acetic acid salt or a halide of a metal such as nickel, cobalt, iron, copper, zinc, etc.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel dipyrromethene metal chelate compound and an optical recording medium using the same, which can record and reproduce data at a higher density than before.

[0002]

2. Description of the Related Art At present, a DVD having a capacity of 4.7 GB has been developed and commercialized as an optical recording medium having a larger capacity than a CD. Since a DVD is a read-only medium, an optical recording medium capable of recording and reproducing data corresponding to the capacity is desired. Among them, the write-once type is called DVD-R.

[0003] In order to perform high-density recording in DVDs, the oscillation wavelength of laser light is shorter than 630 nm to 680 nm as compared with CDs. Dyes of such organic dye-based optical recording media for short wavelength use include cyanine, azo,
Benzopyran, benzodifuranone, indigo, dioxazine, porphyrin dyes and the like have been proposed, JP-A-4-74690, JP-A-5-38878,
JP-A-6-40161, JP-A-6-40162, JP-A-6-199045, JP-A-6-33
6086, JP-A-7-76169, JP-A-7-125441, JP-A-7-262604, JP-A-9-156218, JP-A-9-193
544, JP-A-9-193545, JP-A-9-193747, JP-A-9-194748, JP-A-9-202052, JP-A-9-267
562, JP-A-9-274732 and the like, there is a problem of durability, especially a problem specific to a short wavelength application, for example, a place where a small pit should be opened with a narrowed laser beam has an influence on surroundings. There is no solution to the problem of large pits with large distribution, increased jitter, worse crosstalk in the radial direction, or extremely small pits and insufficient modulation. Is the current situation.

[0004]

SUMMARY OF THE INVENTION An object of the present invention is to provide a novel dipyrromethene metal chelate compound and a high-density recording medium containing the same, which can be recorded and reproduced with a short wavelength laser having a wavelength of 520 to 690 nm. An optical recording medium is provided.

[0005]

Means for Solving the Problems The present inventors have made intensive studies to solve the above-mentioned problems, and as a result, completed the present invention. That is, the present invention provides a dipyrromethene metal chelate compound of a dipyrromethene compound represented by the following general formula (1) and a metal ion:

[0006]

Embedded image

Wherein R ₁ , R ₂ , R ₃ , R ₄ and R ₅ each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a carboxyl group, a sulfonic acid group, C1-C20 alkyl, halogenoalkyl, alkoxyalkyl, alkoxy, alkoxyalkoxy, aryloxy, dialkylaminoalkoxy, alkylthioalkyl, alkylthioalkoxy, acyl, alkoxycarbonyl, alkylamino Carbonyl group, dialkylaminocarbonyl group, alkylcarbonylamino group, arylcarbonylamino group, arylaminocarbonyl group, aryloxycarbonyl group, aralkyl group, aryl group, arylsulfonyl group, arylthio group, heteroaryl group,
Heteroaryloxy group, heteroarylthio group, heteroarylsulfonyl group, alkylthio group, alkenyloxycarbonyl group, aralkyloxycarbonyl group,
Alkoxycarbonylalkoxycarbonyl group, alkylcarbonylalkoxycarbonyl group, hydroxyalkylaminocarbonyl group, di (hydroxyalkyl) aminocarbonyl group, alkoxyalkylaminocarbonyl group, di (alkoxyalkyl) aminocarbonyl group or alkenyl group having 2 to 20 carbon atoms And A represents a substituted or unsubstituted heterocyclic ring and a naphthalene ring. A dipyrromethene metal chelate compound represented by the following general formula (2):

[0008]

Embedded image

Wherein R ₁ , R ₂ , R ₃ , R ₄ and R ₅ have the same meaning as in formula (1), M is nickel, cobalt,
Represents iron, ruthenium, rhodium, palladium, copper, osmium, iridium, platinum, manganese or zinc]

A dipyrromethene metal chelate compound represented by the following general formula (3):

[0011]

Embedded image

[Wherein, R₁, R_Two, R_Three, R_FourAnd R_FiveIs
Represents the same meaning as in equation (1), and X₁And X _TwoIs carbon number 1-2
0 alkyl group, halogenoalkyl group, alkoxyalkyl
Kill group, alkylthioalkyl group, dialkylamino
Alkyl, alkoxy, alkoxyalkoxy
Xy, alkylthioalkoxy, dialkylamido
Alkoxyalkoxy, alkylthio, alkoxy
Silalkylthio group, alkylthiocarbonylalkylthio
O group, dialkylaminoalkylthio group, aryloxy
Si, arylthio, heteroaryl, heteroaryl
Oxy group, heteroarylthio group and halogen atom
The optical recording medium having at least a recording layer and a reflective layer on a substrate
In the recording medium, in the recording layer, any of-
Recording medium containing dipyrromethene metal chelate compound
Body, laser selected from the wavelength range of 520-690 nm
-Optical recording that can be recorded and reproduced with respect to light
Media.

[0013]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Specific examples of the dipyrromethene metal chelate compound represented by the general formula (1) contained in the recording layer of the present invention will be described below.

Specific examples of R ₁ , R ₂ , R ₃ , R ₄ and R ₅ include a hydrogen atom; a nitro group; a cyano group;
Amino group; carboxy group; sulfone group; fluorine, chlorine,
Halogen atom of bromine or iodine; methyl group, ethyl group, n
-Propyl group, iso-propyl group, n-butyl group, iso-
Butyl group, sec-butyl group, t-butyl group, n-pentyl group, iso-pentyl group, 2-methylbutyl group, 1-
Methylbutyl group, neo-pentyl group, 1,2-dimethylpropyl group, 1,1-dimethylpropyl group, cyclopentyl group, n-hexyl group, 4-methylpentyl group, 3
-Methylpentyl group, 2-methylpentyl group, 1-methylpentyl group, 3,3-dimethylbutyl group, 2,3-dimethylbutyl group, 1,3-dimethylbutyl group, 2,2-
Dimethylbutyl group, 1,2-dimethylbutyl group, 1,1
-Dimethylbutyl group, 3-ethylbutyl group, 2-ethylbutyl group, 1-ethylbutyl group, 1,2,2-trimethylbutyl group, 1,1,2-trimethylbutyl group, 1-ethyl-2-methylpropyl group, Cyclo-hexyl group, n
-Heptyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 5-methylhexyl group, 2,4-dimethylpentyl group, n-octyl group, 2
-Ethylhexyl group, 2,5-dimethylhexyl group,
2,5,5-triethylpentyl group, 2,4-dimethylhexyl group, 2,2,4-trimethylpentyl group, n-
Nonyl group, 3,5,5-trimethylhexyl group, n-decyl group, 4-ethyloctyl group, 4-ethyl-4,5-
Dimethylhexyl group, n-undecyl group, n-dodecyl group, 1,3,5,7-tetramethyloctyl group, 4-butyloctyl group, 6,6-diethyloctyl group, n-tridecyl group, 6-methyl- 4-butyloctyl group, 6,
6-diethyloctyl group, n-tetradecyl group, n-pentadecyl group, 3,5-dimethylheptyl group, 2,6-
Dimethylheptyl group, 2,4-dimethylheptyl group,
1,2,5,5-tetramethylhexyl group, 1-cyclo-pentyl-2,2-dimethylpropyl group, 1-cyclo-hexyl-2,2-dimethylpropyl group, etc.
-20 linear, branched or cyclic alkyl groups;

Halogenoalkyl groups such as chloromethyl group, dichloromethyl group, fluoromethyl group, trifluoromethyl group, pentafluoroethyl group and nonafluorobutyl group; methoxyethyl group, ethoxyethyl group, iso-propyloxyethyl group; Alkoxyalkyl groups such as 3-methoxypropyl group and 2-methoxybutyl group; methoxy group, ethoxy group, n-propoxy group, iso-propoxy group, n-butoxy group, iso-butoxy group, sec-butoxy group, t- Alkoxy groups such as butoxy group, n-pentoxy group, iso-pentoxy group, neo-pentoxy group, n-hexyloxy group, n-dodecyloxy group; methoxyethoxy group, ethoxyethoxy group, 3-methoxypropyloxy group, 3 An alkoxyalkoxy group such as -iso-propyloxypropyloxy group; Mill group, an acetyl group, ethylcarbonyl group, n- propyl group,
acyl groups such as iso-propylcarbonyl group, n-butylcarbonyl group, n-pentylcarbonyl group, iso-pentylcarbonyl group, neo-pentylcarbonyl group, 2-methylbutylcarbonyl group and nitrobenzylcarbonyl group; methoxycarbonyl group; An ethoxycarbonyl group,
alkoxycarbonyl groups such as iso-propyloxycarbonyl group and 2,4-dimethylbutyloxycarbonyl group;

Methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, n-
Alkylaminocarbonyl groups such as butylaminocarbonyl group and n-hexylaminocarbonyl group; alkylcarbonylamino groups such as acetylamino group, ethylcarbonylamino group and n-butylcarbonylamino group; phenoxy group, 2-methylphenoxy group, 4 Aryloxy groups such as -methylphenoxy group, 4-t-butylphenoxy group, 2-methoxyphenoxy group, 4-iso-propylphenoxy group; phenylaminocarbonyl group, 4-methylphenylaminocarbonyl group, 2-methoxyphenylamino Arylaminocarbonyl groups such as carbonyl group and 4-n-propylphenylaminocarbonyl group; dimethylaminocarbonyl group, diethylaminocarbonyl group, di-
dialkylaminocarbonyl groups such as n-propylaminocarbonyl group, di-n-butylaminocarbenyl group, N-methyl-N-cyclohexylaminocarbonyl group; 2
-Methylthioethoxy group, 2-ethylthioethoxy group,
2-n-propylthioethoxy group, 2-iso-propylthioethoxy group, 2-n-butylthioethoxy group, 2-
an alkylthioalkoxy group of an iso-butylthioethoxy group;

Aryloxycarbonyl groups such as phenoxycarbonyl group, 2-methylphenoxycarbonyl group, 4-methoxyphenylcarbonyl group and 4-t-butylphenoxycarbonyl group; phenylcarbonylamino group;
Arylcarbonylamino groups such as 4-ethylphenylcarbonylamino group and 3-butylphenylcarbonylamino group; benzyl group, nitrobenzyl group, cyanobenzyl group, hydroxybenzyl group, methylbenzyl group, trimethylbenzyl group, dichlorobenzyl group, methoxy Aralkyl groups such as benzyl, ethoxybenzyl, trifluoromethylbenzyl, naphthylmethyl, nitronaphthylmethyl, cyanonaphthylmethyl, trifluoromethylnaphthylmethyl; phenyl, nitrophenyl, cyanophenyl, hydroxy Phenyl, methylphenyl, dimethylphenyl, trimethylphenyl, dichlorophenyl, methoxyphenyl, ethoxyphenyl, trifluoromethylphenyl, N, N
Aryl groups such as dimethylaminophenyl, naphthyl, nitronaphthyl, cyanonaphthyl, hydroxynaphthyl, methylnaphthylmethyl, trifluoromethylnaphthylmethyl; pyrrolyl, thienyl, furanyl, oxazoyl, isoxazoyl Heteroaryl groups such as a group, a benzoxazoyl group, a pyridyl group, an imidazoyl group, a benzothiazoyl group, a benzimidazoyl group, a benzofuranyl group and an indolyl group;

Methylthio, ethylthio, n-propylthio, iso-propylthio, n-butylthio, i
so-butylthio group, sec-butylthio group, t-butylthio group, n-pentylthio group, iso-pentylthio group, 2
-Methylbutylthio group, 1-methylbutylthio group, neo
-Pentylthio group, 1,2-dimethylpropylthio group,
Alkylthio groups such as 1,1-dimethylpropylthio group;
Arylthio groups such as phenylthio group, 4-methylphenylthio group, 2-methoxyphenylthio group and 4-t-butylphenylthio group; alkenyloxycarbonyl groups such as allyloxycarbonyl group and 2-butenoxycarbonyl group; benzyl Aralkyloxycarbonyl groups such as oxycarbonyl group and phenethyloxycarbonyl group; alkoxycarbonylalkoxycarbonyl groups such as methoxycarbonylmethoxycarbonyl group, ethoxycarbonylmethoxycarbonyl group, n-propoxycarbonylmethoxycarbonyl group and isopropoxycarbonylmethoxycarbonyl group;

A methylcarbonylmethoxycarbonyl group,
Alkylcarbonylalkoxycarbonyl groups such as ethylcarbonylmethoxycarbonyl group; mono (hydroxyalkyl) aminocarbonyl groups such as 2-hydroxyethylaminocarbonyl group, 2-hydroxypropylaminocarbonyl group and 3-hydroxypropylaminocarbonyl group; di (hydroxy Di (hydroxyalkyl) aminocarbonyl groups such as ethyl) aminocarbonyl group, di (2-hydroxypropyl) aminocarbonyl group and di (3-hydroxypropyl) aminocarbonyl group; methoxymethylaminocarbonyl group, 2-methoxyethylaminocarbonyl Group, ethoxymethylaminocarbonyl group, 2
Mono (alkoxyalkyl) aminocarbonyl groups such as -ethoxyethylaminocarbonyl group, propoxymethylaminocarbonyl group, 2-ethoxyethylaminocarbonyl group, 2-propoxyethylaminocarbonyl group;

Di (alkoxyalkyl) aminocarbonyl groups such as di (methoxyethyl) aminocarbonyl group, di (ethoxymethyl) aminocarbonyl group, di (ethoxyethyl) aminocarbonyl group and di (propoxyethyl) aminocarbonyl group; A hydroxyethoxy group,
Hydroxyalkoxy groups such as 3-hydroxypropoxy group, 5-hydroxypentyloxy group, 4-hydroxy-cyclo-hexyloxy group; vinyl group, propenyl group, 1-butenyl group, iso-butenyl group, 1-pentenyl group, 2 -Pentenyl group, 2-methyl-1-butenyl group, 3-methyl-1-butenyl group, 2-methyl-2-butenyl group, 2,2-dicyanovinyl group, 2-cyano-2
Alkenyl having 2 to 20 carbon atoms such as -methylcarboxylvinyl group and 2-cyano-2-methylsulfonevinyl group.

In the dipyrromethene compound represented by the general formula (1), specific examples of the unsubstituted heterocyclic ring represented by A include pyridine, pyridazine, pyrimidine, pyrazine, furan, thiophene, pyrrole, oxazole, thiazole, indole Chromene, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, phthalazine, pteridine and the like. Further, these heterocyclic ring and naphthalene ring may be substituted, in which case, as a substituent, an alkyl group, an alkoxy group, an aryloxy group, an aralkyl group, an aryl group, a halogen atom, a cyano group, a nitro group, Examples include an ester group, a carbamoyl group, an acyl group, an acylamino group, a sulfamoyl group, a sulfonamide group, an amino group, a hydroxyl group, a thiol group, a carboxylic acid group, and a sulfonic acid group.

Specific examples of X ₁ and X ₂ include methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec-butyl, t-butyl and n-butyl. -Pentyl group, iso-pentyl group, 2-methylbutyl group, 1-methylbutyl group, neo-pentyl group, 1,
2-dimethylpropyl group, 1,1-dimethylpropyl group, cyclopentyl group, n-hexyl group, 4-methylpentyl group, 3-methylpentyl group, 2-methylpentyl group, 1-methylpentyl group, 3, 3-dimethylbutyl group, 2,3-dimethylbutyl group, 1,3-dimethylbutyl group, 2,2-dimethylbutyl group, 1,2-dimethylbutyl group, 1,1-dimethylbutyl group, 3-ethylbutyl group , 2-ethylbutyl group, 1-ethylbutyl group, 1,
2,2-trimethylbutyl group, 1,1,2-trimethylbutyl group, 1-ethyl-2-methylpropyl group, cyclo-hexyl group, n-heptyl group, 2-methylhexyl group, 3-methylhexyl group, 4-methylhexyl group, 5
-Methylhexyl group, 2,4-dimethylpentyl group, n
-Octyl group, 2-ethylhexyl group, 2,5-dimethylhexyl group, 2,5,5-triethylpentyl group,
2,4-dimethylhexyl group, 2,2,4-trimethylpentyl group, n-nonyl group, 3,5,5-trimethylhexyl group, n-decyl group, 4-ethyloctyl group, 4-
Ethyl-4,5-dimethylhexyl group, n-undecyl group, n-dodecyl group, 1,3,5,7-tetramethyloctyl group, 4-butyloctyl group, 6,6-diethyloctyl group, n-tridecyl Group, 6-methyl-4-butyloctyl group, 6,6-diethyloctyl group, n-tetradecyl group, n-pentadecyl group, 3,5-dimethylheptyl group, 2,6-dimethylheptyl group, 2,4- 1 to 1 carbon atoms such as a dimethylheptyl group, a 2,2,5,5-tetramethylhexyl group, a 1-cyclo-pentyl-2,2-dimethylpropyl group and a 1-cyclo-hexyl-2,2-dimethylpropyl group. 20 linear, branched or cyclic alkyl groups;

Halogenoalkyl groups such as chloromethyl group, dichloromethyl group, fluoromethyl group, trifluoromethyl group, pentafluoroethyl group and nonafluorobutyl group; methoxyethyl group, ethoxyethyl group, iso-propyloxyethyl group; Alkoxyalkyl groups such as 3-methoxypropyl group and 2-methoxybutyl group; 2-methylthioethyl group, 2-ethylthioethyl group, 2-n-propylthioethyl group, 2-iso-propylthioethyl group,
Alkylthioalkyl group of 2-n-butylthioethyl group, 2-iso-butylthioethyl group; 2-dimethylaminoethyl group, 2- (2-dimethylaminoethoxy) ethyl group, 4-dimethylaminobutyl group, 1- Dimethylaminopropan-2-yl group, 3-dimethylaminopropyl group, 2-dimethylamino-2-methylpropyl group, 2-
Straight chain such as diethylaminoethyl, 2-2-diethylaminoethoxyethyl, 3-diethylaminopropyl, 1-diethylaminopropyl, 2-di-iso-propylaminoethyl, 2-di-n-butylaminoethyl, etc. Branched dialkylaminoalkyl groups; methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, iso-butoxy, sec-butoxy, t-butoxy, n-pentoxy, iso- Pentoxy group, neo-pentoxy group, n-hexyloxy group, n-dodecyloxy group, cyclohexyloxy group,
Alkoxy groups such as 4-methylcyclohexyloxy group, 4-ethylcyclohexyl group, 2-n-propylcyclohexyloxy group, 4-t-butylcyclohexyloxy group, adamantane-1-yloxy group, and borneol group;

2-methoxyethoxy group, 1-methoxybutan-2-yloxy group, 1-methoxybutan-1-yloxy group, 1-methoxypropan-2-yloxy group, 2- (2-methoxyethoxy) ethoxy group, 2-ethoxyethoxy group, 2-ethoxypropan-2-yloxy group, 2-iso-propoxyethoxy group, 2-butoxyethoxy group, 2-iso-butoxyethoxy group, 2-t
-Butoxyethoxy group, 2- (2-butoxyethoxy)
A linear or branched alkoxyalkoxy group such as an ethoxy group; a 2-dimethylaminoethoxy group, a 2- (2-dimethylaminoethoxy) ethoxy group, a 4-dimethylaminobutoxy group, a 1-dimethylaminopropan-2-yloxy group, 3-dimethylaminopropoxy group, 2-dimethylamino-2-methylpropoxy group, 2-diethylaminoethoxy group, 2- (2-diethylaminoethoxy) ethoxy group, 3-diethylaminopropoxy group, 1-diethylaminopropoxy group, 2-di Linear or branched dialkylaminoalkoxy groups such as -iso-propylaminoethoxy group, 2-di-n-butylaminoethoxy group; phenoxy group, 2-methylphenoxy group, 4-methylphenoxy group, 4-t-butyl Phenoxy group, 2-methoxyphenoxy group, 4-iso-p Pirufenokishi aryloxy group such as a group; methylthio group, ethylthio group, n- propylthio group, iso- propylthio group, n- butylthio group, i
so-butylthio group, sec-butylthio group, t-butylthio group, n-pentylthio group, iso-pentylthio group, 2
-Methylbutylthio group, 1-methylbutylthio group, neo
-Pentylthio group, 1,2-dimethylpropylthio group,
Alkylthio groups such as 1,1-dimethylpropylthio group;
Arylthio groups such as phenylthio group, 4-methylphenylthio group, 2-methoxyphenylthio group, and 4-t-butylphenylthio group; and halogen atoms of fluorine, chlorine, bromine and iodine.

The metal forming a chelate compound together with the dipyrromethene compound represented by the general formula (1) includes
Generally, there is no particular limitation as long as the metal has the ability to form a chelate compound with a dipyrromethene-based compound, but transition elements such as nickel, cobalt, iron, ruthenium, rhodium, palladium, copper, osmium, iridium, platinum, manganese, and zinc, A boron atom is preferred.

The dipyrromethene metal chelate compound of the present invention represented by the general formula (1) and a metal ion can be easily produced as follows. That is, typically, first, a compound represented by the general formula (4) and a compound represented by the general formula (5) or a compound represented by the general formula (6) in the presence of an acid catalyst such as hydrobromic acid and hydrogen chloride. ) Is reacted with a compound represented by the general formula (7) to produce a dipyrromethene compound represented by the general formula (1). Then, in order to produce the dipyrromethene metal chelate compound represented by the general formula (2), the obtained dipyrromethene-based compound represented by the general formula (1)
React with acetates and halides such as nickel, cobalt, iron, ruthenium, rhodium, palladium, copper, osmium, iridium, platinum, manganese and zinc. or,
In order to produce the dipyrromethene metal chelate compound represented by the general formula (3), the obtained dipyrromethene compound represented by the general formula (1) is reacted with boron trifluoride or boron trichloride, The compounds thus obtained wherein X ₁ and X ₂ are halogen atoms include alkoxides such as sodium methoxide and potassium ethoxide, phenoxides such as sodium phenoxide and sodium-2-methoxyphenoxide, and butylmagnesium bromide. Butyllithium, phenylmagnesium bromide, and other organometallic reagents, thiol salts such as sodium methylmercaptan, and sodium 4-t-butylphenylthiol, and the like, to replace the halogen atom to obtain the desired compound. .

[0027]

Embedded image (In the formula, R ₄ , R ₅ and A are the same as described above.)

[0028]

Embedded image (In the formula, R ₁ , R ₂ and R ₃ are the same as described above.)

[0029]

Embedded image (In the formula, R ₅ and A are the same as described above.)

[0030]

Embedded image (In the formula, R ₁ , R ₂ , R ₃ and R ₄ are the same as described above.)

Specific examples of the dipyrromethene metal chelate compound of the dipyrromethene compound represented by the general formula (1) and a metal ion include compounds having a substituent and a metal shown in Tables 1 and 2. Table-1 and Table-
The substituents shown in 2 are the substituents of the general formulas (2) and (3), respectively.

[0032]

[Table 1]

[0033]

[Table 2]

[0034]

[Table 3]

The specific structure of the present invention will be described below. The optical recording medium of the present invention has a bonding structure as shown in FIG. That is, the recording layer 2 is formed on the substrate 1, the reflective layer 3 is provided in close contact with the recording layer 2, and the substrate 5 is bonded thereon via the adhesive layer 4. However, another layer may be provided below or above the recording layer 2, and another layer may be provided above the reflective layer 3.

As a material of the substrate, basically, any material may be used as long as it is transparent at the wavelength of the recording light and the reproducing light. For example, polymer materials such as acrylic resins such as polycarbonate resin, vinyl chloride resin and polymethyl methacrylate, polystyrene resins and epoxy resins, and inorganic materials such as glass are used.
These substrate materials are formed into a disk shape by injection molding or the like. If necessary, guide grooves or pits may be formed on the substrate surface. Such guide grooves and pits
It is desirable to apply it at the time of molding the substrate, but it can also be applied using an ultraviolet curable resin layer on the substrate. When used as a normal DVD, it is a disk having a thickness of about 1.2 mm and a diameter of about 80 to 120 mm, and a hole having a diameter of about 15 mm is formed in the center.

In the present invention, a recording layer is provided on a substrate. The recording layer of the present invention has an absorption maximum of 450 nm or more.
It contains a dipyrromethene metal chelate compound of a dipyrromethene compound represented by the general formula (1) present at about 630 nm and a metal ion. Among them, 520 nm to 690
It is necessary to have an appropriate optical constant for a recording and reproducing laser wavelength selected from nm.

The optical constant is represented by a complex refractive index (n + ki) (i represents an imaginary unit). N and k in the expression are coefficients corresponding to the real part n and the imaginary part k. Here, n is a refractive index, and k is an extinction coefficient.

In general, the refractive index and extinction coefficient of an organic dye show a large wavelength dependence. In consideration of this feature, by selecting an organic dye having a preferable optical constant at the target laser wavelength and forming a recording layer, it has a high reflectance, and can be a medium with high sensitivity. it can.

According to the present invention, the optical constant required for the recording layer is such that n is 1.8 or more at the wavelength of the laser light,
And k is 0.04 to 0.40, preferably n
Is 2. 0 or more, and k is 0.04 to 0.20. If n is smaller than 1.8, the reflectance and signal modulation required for accurate signal reading cannot be obtained, and k is 0.4.
If the value exceeds 0, not only is the reflectance lowered and a good reproduction signal cannot be obtained, but also the signal is easily changed by the reproduction light, which is not suitable for practical use. In consideration of this feature, by selecting an organic dye having a preferable optical constant at the target laser wavelength and forming a recording layer, having a high reflectance, and,
A medium with good sensitivity can be obtained. The dipyrromethene metal chelate compound of the dipyrromethene compound represented by the general formula (1) and a metal ion used in the present invention has a preferable optical constant as described above.

The optical recording medium of the present invention has a thickness of 520 nm to 690.
Reproduction with a laser beam selected from nm is basically possible if the reflectivity is 20%.
% Is preferred.

In order to improve recording characteristics and the like, a wavelength of 4
It has an absorption maximum at 50 nm to 630 nm, and
It may be mixed with other dyes having a large refractive index at 690 nm. Specifically, cyanine dyes, squarylium dyes, naphthoquinone dyes, anthraquinone dyes,
Porphyrin dyes, tetrapyraporphyrazine dyes, indophenol dyes, pyrylium dyes, thiopyrylium dyes, azurenium dyes, triphenylmethane dyes, xanthene dyes, indathrene dyes, indigo dyes, thioindigo dyes And merocyanine dyes, thiazine dyes, acridine dyes, oxazine dyes, and the like, and a mixture of a plurality of dyes may be used. The mixing ratio of these dyes is about 0.1% to 30%.

When forming the recording layer, if necessary, a quencher, a dye decomposition accelerator, an ultraviolet absorber, an adhesive, or the like is mixed with the above-mentioned dye, or a compound having such an effect. Can be introduced as a substituent of the dye.

Specific examples of the quencher include metal such as bisacetylthionates, bisdithio-α-diketones, bisdithiols such as bisphenyldithiols, thiocatechols, salicylaldehyde oximes, and thiobisphenolates. Complexes are preferred. Amines are also suitable.

Examples of the thermal decomposition accelerator include metal compounds such as metal anti-knocking agents, metallocene compounds, and acetylacetonate metal complexes.

Further, if necessary, a binder, a leveling agent, an antifoaming agent and the like can be used in combination. Preferred binders include polyvinyl alcohol, polyvinylpyrrolidone, nitrocellulose, cellulose acetate,
Ketone resin, acrylic resin, polystyrene resin, urethane resin, polyvinyl butyral, polycarbonate, polyolefin and the like can be mentioned.

When a recording layer is formed on a substrate, in order to improve the solvent resistance, reflectance, recording sensitivity, etc. of the substrate,
A layer made of an inorganic substance or a polymer may be provided on the substrate.

Here, the content of the dipyrromethene metal chelate compound of the dipyrromethene compound represented by the general formula (1) and the metal ion in the recording layer is 30% or more, preferably 60% or more. In addition, it is also preferable that it is substantially 100%.

Examples of the method for providing the recording layer include coating methods such as spin coating, spraying, casting, and dipping, sputtering, chemical vapor deposition, and vacuum vapor deposition. Is preferred.

When a coating method such as a spin coating method is used, a dipyrromethene metal chelate compound of a dipyrromethene compound represented by the general formula (1) and a metal ion may be used in an amount of 1 to 1
A coating solution dissolved or dispersed in a solvent is used in an amount of 40% by weight, preferably 3 to 30% by weight. At this time, it is preferable to select a solvent that does not damage the substrate. For example, alcohol solvents such as methanol, ethanol, isopropyl alcohol, octafluoropentanol, allyl alcohol, methyl cellosolve, ethyl cellosolve, and tetrafluoropropanol, hexane, heptane, octane, decane, cyclohexane, methylcyclohexane, ethylcyclohexane, dimethylcyclohexane Aliphatic or alicyclic hydrocarbon solvents such as, toluene, xylene, aromatic hydrocarbon solvents such as benzene, carbon tetrachloride, chloroform, tetrachloroethane, halogenated hydrocarbon solvents such as dibromoethane, diethyl ether, Ether solvents such as dibutyl ether, diisopropyl ether, dioxane,
Examples include ketone solvents such as acetone and 3-hydroxy-3-methyl-2-butanone, ester solvents such as ethyl acetate and methyl lactate, and water. These may be used alone or in combination.

If necessary, the dye of the recording layer may be dispersed in a polymer thin film or the like.

When a solvent that does not damage the substrate cannot be selected, a sputtering method, a chemical vapor deposition method, a vacuum vapor deposition method, or the like is effective.

The thickness of the dye layer is not particularly limited, but is preferably 50 nm to 300 nm. If the thickness of the dye layer is less than 50 nm, recording cannot be performed due to large thermal diffusion, or a recording signal will be distorted and the signal amplitude will be small. On the other hand, when the film thickness is larger than 300 nm, the reflectivity decreases and the reproduction signal characteristics deteriorate.

Next, on the recording layer, preferably 50 nm
A reflective layer having a thickness of 300 nm is formed. As a material of the reflection layer, a material having sufficiently high reflectance at the wavelength of the reproduction light, for example, Au, Al, Ag, Cu, Ti, Cr, Ni, P
The metals t, Ta, Cr and Pd can be used alone or as an alloy. Among them, Au, Al,
Ag has a high reflectance and is suitable as a material for the reflective layer. In addition, the following may be included. For example, M
g, Se, Hf, V, Nb, Ru, W, Mn, Re, F
e, Co, Rh, Ir, Zn, Cd, Ga, In, S
Examples include metals such as i, Ge, Te, Pb, Po, Sn, and Bi and metalloids. Further, those containing Au as a main component are preferable because a reflection layer having high reflectance can be easily obtained. Here, the main component means a component having a content of 50% or more. It is also possible to form a multilayer film by alternately stacking low-refractive-index thin films and high-refractive-index thin films with a material other than a metal, and use it as a reflective layer.

As a method of forming the reflection layer, for example,
Examples include a sputtering method, an ion plating method, a chemical vapor deposition method, and a vacuum vapor deposition method. In addition, a known inorganic or organic intermediate layer or adhesive layer may be provided on the substrate or below the reflective layer to improve the reflectance, the recording characteristics, and the adhesion.

The material of the protective layer on the reflective layer is not particularly limited as long as it protects the reflective layer from external force. As organic substances, thermoplastic resins, thermosetting resins,
An electron beam curable resin, an ultraviolet curable resin, and the like can be given. Further, as the inorganic substance, SiO ₂ , Si ₃ N
₄ , MgF ₂ , SnO _{2 and the} like. A thermoplastic resin, a thermosetting resin, or the like can be formed by dissolving in a suitable solvent, applying a coating solution, and drying. The ultraviolet curable resin is applied as it is or after dissolving it in an appropriate solvent to prepare a coating solution,
It can be formed by irradiating and curing ultraviolet rays. As the ultraviolet curable resin, for example, acrylate resins such as urethane acrylate, epoxy acrylate, and polyester acrylate can be used. These materials may be used alone or as a mixture, and may be used not only as a single layer but also as a multilayer film.

As a method of forming the protective layer, a coating method such as a spin coating method or a casting method, a sputtering method or a chemical vapor deposition method is used as in the recording layer. Of these, the spin coating method is preferable.

The thickness of the protective layer is generally 0.1 μm to 1 μm.
In the present invention, the range is from 3 μm to
It is 30 μm, more preferably 5 μm to 20 μm.

A label or the like can be further printed on the protective layer.

Alternatively, a protective sheet or a substrate may be bonded to the reflective layer surface, or two optical recording media may be bonded together with the reflective layer surfaces facing each other.

Further, an ultraviolet curable resin, an inorganic thin film, or the like may be formed on the mirror surface of the substrate to protect the surface and prevent adhesion of dust and the like.

The wavelength of 520 to 690 nm in the present invention
The laser is not particularly limited. For example, a dye laser capable of selecting a wavelength in a wide range of a visible light region or a wavelength of 633 is used.
helium-neon laser, high-power semiconductor lasers with wavelengths of around 680, 650, and 635 nm, and a harmonic conversion YAG laser with a wavelength of 532 nm. According to the present invention, high-density recording and reproduction can be performed at one wavelength or a plurality of wavelengths selected from these.

[0063]

EXAMPLES Examples of the present invention will be shown below, but the present invention is not limited thereto.

Example 1 Synthesis of dipyrromethene metal chelate compound (2-1) 0.28 g of 1-phenyl-4-azaisoindole and 2-formyl-3,5 in 50 mL of ethanol under a nitrogen stream.
-Diphenylpyrrole (0.36 g) was dissolved, 47% -hydrobromic acid (0.26 g) was added dropwise, and the mixture was stirred at reflux temperature for 1 hour. After evaporating the solvent, toluene was added to the residue, and after washing with water, hexane was added to the concentrated residue. The precipitated crystals were collected by filtration, washed with hexane, and represented by the following structural formula (1-a). 0.46 g of the compound obtained was obtained.

[0065]

Embedded image

[0066]

[Table 4]

Next, under a nitrogen stream, 0.17 g of the compound represented by the formula (1-a) is dissolved in 30 mL of ethanol, 0.86 g of copper acetate monohydrate is added, and the mixture is stirred at reflux temperature for 3 hours. did. After cooling, the precipitate was collected by filtration, washed with water, and then washed with ethanol to give the compound represented by the following structural formula (2-1) in 0.1.
13 g were obtained.

[0068]

Embedded image

From the following analysis results, it was confirmed that the substance was the target substance.

[0070]

[Table 5]

The compound thus obtained showed a maximum absorption at 590 nm in a toluene solution, and had a gram extinction coefficient of 0.73 × 10 ⁵ mL / g · cm.

Example 2 Synthesis of dipyrromethene metal chelate compound (2-2) In a nitrogen stream, 2.6 g of 1- (2,4-diisopropylphenyl) -benzo [f] isoindole and 150 g of 2-formyl were added to 150 mL of ethanol. After dissolving 1.2 g of -3,5-dimethyl-4-ethylpyrrole and dropping 1.4 g of 47% -hydrobromic acid, the mixture was stirred at room temperature for 2 hours and further at 45 ° C. for 1 hour. After the solvent was distilled off, toluene was added to the residue, washed with water, and the concentrated residue was subjected to column purification to give a compound 2.15 represented by the following structural formula (1-b).
g was obtained.

[0073]

Embedded image

From the following analysis results, it was confirmed that (1-b).

[0075]

[Table 6]

Then, under a nitrogen stream, 0.1 g of the compound represented by the formula (1-b) was dissolved in 300 mL of ethanol, and 0.57 g of bis (acetylacetonato) copper (II) was added.
Stirred at reflux temperature for 16 hours. After distilling off 150 mL of the solvent and cooling, the precipitate was collected by filtration, washed with water, and then washed with ethanol to obtain 0.26 g of a compound represented by the following structural formula (2-2).

[0077]

Embedded image

From the following analysis results, it was confirmed that the target substance was obtained.

[0079]

[Table 7]

The compound thus obtained exhibited a maximum absorption at 601 nm in a toluene solution, and had a gram extinction coefficient of 0.45 × 10 ⁵ mL / g · cm.

[Example 3] Synthesis of dipyrromethene metal chelate compound (2-3) Then, under a nitrogen stream, 100 mL of ethanol was added to formula (1-b).
Was dissolved, 0.24 g of zinc acetate dihydrate was added, and the mixture was stirred at reflux temperature for 5 hours. The solvent was distilled off after distilling off 50 mL, and the precipitate was collected by filtration, washed with water, and then washed with ethanol to obtain 0.33 mg of a compound represented by the following structural formula (2-3).

[0082]

Embedded image

From the following analysis results, it was confirmed that the product was the target product.

[0084]

[Table 8]

The compound thus obtained exhibited a maximum absorption at 596 nm in a toluene solution, and had a gram extinction coefficient of 1.58 × 10 ⁵ mL / g · cm.

Example 4 Synthesis of dipyrromethene metal chelate compound (2-4) Next, under a nitrogen stream, 500 mL of ethanol was added to the formula (1-b).
Was dissolved, 1.08 g of cobalt acetate tetrahydrate was added, and the mixture was stirred at reflux temperature for 5 hours. After distilling off 300 mL of the solvent and cooling, the precipitate was collected by filtration, washed with water, and washed with ethanol to obtain 0.59 g of a compound represented by the following structural formula (2-4).

[0087]

Embedded image

From the following analysis results, it was confirmed that the substance was the target substance.

[0089]

[Table 9]

The compound thus obtained showed a maximum absorption at 639 nm in a toluene solution, and had a gram extinction coefficient of 0.64 × 10 ⁵ mL / g · cm.

Example 5 Synthesis of Pyromethene Metal Chelate Compound (2-5) Under a nitrogen stream, 1.7 g of 1-toluyl-benzo [f] isoindole and 125 g of 2-formyl- were added to 125 mL of ethanol.
After dissolving 1.0 g of 3,5-dimethyl-4-ethylpyrrole and dropping 1.2 g of 47% -hydrobromic acid, the mixture was stirred at room temperature for 2 hours and further at 45 ° C. for 1 hour. After the solvent was distilled off, toluene was added to the residue, and after washing with water, the concentrated residue was purified by column to obtain 1.3 g of a compound represented by the following structural formula (1-c).

[0092]

Embedded image

From the following analysis results, it was confirmed that the value was (1-c).

[0094]

[Table 10]

Next, 200 mg of the compound represented by the formula (1-c) was dissolved in 50 mL of ethanol under a nitrogen stream, 0.11 g of zinc acetate dihydrate was added, and the mixture was stirred at reflux temperature for 2 hours. After evaporating 25 mL of the solvent, the mixture was cooled, and the precipitate was collected by filtration.
After washing with water, the precipitate was washed with ethanol to obtain 0.17 g of a compound represented by the following structural formula (2-5).

[0096]

Embedded image

From the following analysis results, the product was confirmed to be the target product.

[0098]

[Table 11]

The compound thus obtained showed a maximum absorption at 603 nm in a toluene solution, and had a gram extinction coefficient of 1.29 × 10 ⁵ mL / g · cm.

Example 6 Synthesis of Pyromethene Metal Chelate Compound (2-6) Next, 0.2 g of the compound represented by the formula (1-c) was dissolved in 50 mL of ethanol under a nitrogen stream, and cobalt acetate 4 0.13 g of hydrate was added and stirred at reflux temperature for 2.5 hours. After distilling off 25 mL of the solvent and cooling, the precipitate was collected by filtration, washed with water, and then washed with ethanol to obtain 0.18 g of a compound represented by the following structural formula (2-6).

[0101]

Embedded image

From the following analysis results, it was confirmed that the substance was the target substance.

[0103]

[Table 12]

The compound thus obtained showed a maximum absorption at 641 nm in a toluene solution, and had a gram extinction coefficient of 0.743 × 10 ⁵ mL / g · cm.

Example 7 Synthesis of Pyromethene Metal Chelate Compound (2-7) Next, 0.2 g of the compound represented by the formula (1-c) was dissolved in 50 mL of ethanol under a nitrogen stream, and bis (acetyl) was added. 0.13 g of (acetonato) copper (II) was added, and the mixture was stirred at reflux temperature for 5 hours. After distilling off 25 mL of the solvent, the mixture was cooled, and the precipitate was collected by filtration, washed with water, and then washed with ethanol to give the following structural formula (2-
0.12 g of the compound represented by 7) was obtained.

[0106]

Embedded image

From the following analysis results, the product was confirmed to be the target product.

[0108]

[Table 13]

The compound thus obtained exhibited a maximum absorption at 615 nm in a toluene solution, and had a gram extinction coefficient of 0.48 × 10 ⁵ mL / g · cm.

Example 8 Synthesis of Pyromethene Metal Chelate Compound (3-1) 3 g of 1-mesityl-benzo [f] isoindole and 100 g of 2-formyl-3,5 in 100 mL of ethanol under a nitrogen stream.
Dissolve 1.6 g of dimethyl-4-ethylpyrrole,
After dropping 2 g of 7% -hydrobromic acid, the mixture was stirred at room temperature for 5 hours. After distilling off the solvent, toluene was added to the residue,
After washing with water, the concentrated residue was purified by column to obtain 3.2 g of a compound represented by the following structural formula (1-d).

[0111]

Embedded image

From the following analysis results, it was confirmed that it was (1-d).

[0113]

[Table 14]

Next, under nitrogen stream, 0.3 g of the compound represented by the formula (1-d) was dissolved in 40 mL of toluene.
-Diisopropylamine (0.15 g) was added, and boron trifluoride ether complex (0.2 g) was added dropwise, followed by stirring at room temperature for 4 hours. After washing the toluene extract with water, the residue obtained by concentrating the toluene was purified by column to obtain the following structural formula (3-
0.25 g of the compound represented by 1) was obtained.

[0115]

Embedded image

From the following analysis results, it was confirmed that the substance was the target substance.

[0117]

[Table 15]

The compound thus obtained showed a maximum absorption at 627.5 nm in a toluene solution, and had a gram extinction coefficient of 1.64 × 10 ⁵ mL / g · cm.

Example 9 Dipyrromethene metal compound (2
-1) 0.2 g was dissolved in 10 ml of dimethylcyclohexane to prepare a dye solution. The substrate is made of a continuous guide groove made of polycarbonate resin (track pitch: 0.8μ).
m), a disk-shaped one having a diameter of 120 mm and a thickness of 0.6 mm was used.

The dye solution was placed on the substrate at a rotational speed of 1500 r.
pm, and dried at 70 ° C for 3 hours to form a recording layer.

Au was sputtered on this recording layer using a sputtering apparatus (CDI-900, manufactured by Balzers) to form a reflective layer having a thickness of 100 nm. Argon gas was used as a sputtering gas. The sputtering was performed under the conditions of a sputtering power of 2.5 kW and a sputtering gas pressure of 1.0 × 10 ⁻² Torr.

Further, an ultraviolet-curable adhesive SD is applied on the reflective layer.
-301 (manufactured by Dainippon Ink and Chemicals) is spin-coated, and a polycarbonate resin having a diameter of 120 m is coated thereon.
After placing a disc-shaped substrate having a thickness of 0.6 mm and a thickness of 0.6 mm, the substrate was laminated by irradiating ultraviolet rays to produce an optical recording medium.

The obtained optical recording medium is equipped with a semiconductor laser head having a wavelength of 635 nm and a lens numerical aperture of 0.6, and an optical disk evaluation apparatus (DDU- manufactured by Pulstec Industrial).
1000) and KENWOOD EFM encoder, linear velocity 3.8 m / s, laser power 10 mW
The recording was performed so that the shortest pit length was 0.40 μm.
After recording, the signal was reproduced using an evaluation device equipped with a 650 nm and 635 nm red semiconductor laser head (the numerical aperture of the lens was 0.6), and the reflectance, jitter and modulation were measured. 52%, jitter 8.8%, modulation degree 0.67, and 635 nm reproduction showed good values of 51%, jitter 8.8% and modulation degree 0.66. No change was observed even after the light resistance test with a carbon arc for 100 hours and the heat and humidity resistance test at 80 ° C. and 85%.

[Examples 10 to 30] An optical recording medium was prepared and recorded in the same manner as in Example 9 except that the dipyrromethene metal chelate compounds described in Tables 1 and 2 were used. After recording, the signal was reproduced using an evaluation device equipped with 650 nm and 635 nm red semiconductor laser heads, and the reflectance, the jitter and the modulation were measured. No change was observed even after the light resistance test with a carbon arc for 100 hours and the heat and humidity resistance test at 80 ° C. and 85%.

In Examples 10 to 30 described above, each optical recording medium was recorded at 635 nm, and 650 and 635n
Table 3 shows the reflectance, jitter, and modulation factor when reproduced at m.
Are shown together. The maximum absorption was measured in a state where the recording layer was formed.

[Comparative Example 1] In Example 9, a pentamethine cyanine dye NK-2929 “1,3,3,1 ′, 3 ′, 3′-hexamethyl-) was used instead of the benzopyrromethene metal compound (2-1). 2 ', 2'-(4,5,4 ', 5'-dibenzo) indodicarbocyanine perchlorate, manufactured by Japan Photographic Dye Laboratories Co., Ltd.'' Thus, an optical recording medium was manufactured. An optical disk evaluation device (DDU-1000) manufactured by Pulstec Industrial having a 635 nm semiconductor laser head mounted on the manufactured medium as in Example 9, and an EFM manufactured by KENWOOD
Recording was performed at a linear velocity of 3.8 m / s and a laser power of 10 mW using an encoder. After recording, the signal was reproduced using an evaluation device equipped with 650 nm and 635 nm red semiconductor laser heads, and the reflectance, jitter, and modulation were measured. As a result, the reflectance was 9%, the jitter was 20% or more, and the modulation was 650 nm. The reflectivity was 9%, the jitter was 20% or more, and the modulation factor was 0.15 at 0.13 and 635 nm reproduction. Also, after the light fastness test with a carbon arc for 100 hours, the signal deteriorated and could not be reproduced.

[0127]

[Table 16]

[0128]

[Table 17]

[0129]

[Table 18]

[0130]

[Table 19]

[0131]

By using the dipyrromethene metal chelate compound of the present invention as a recording layer, it is possible to record / reproduce information with a laser having a wavelength of 520 to 690 nm, which has been attracting much attention as a high-density optical recording medium, and to achieve additional durability. It is possible to provide a type optical recording medium.

[Brief description of the drawings]

FIG. 1 is a sectional structural view showing a conventional optical recording medium and a layer structure of the present invention.

[Explanation of symbols]

 DESCRIPTION OF SYMBOLS 1 Substrate 2 Recording layer 3 Reflective layer 4 Adhesive layer 5 Substrate

────────────────────────────────────────────────── ─── Continued on the front page (51) Int.Cl. ⁶ Identification code FI G11B 7/24 516 G11B 7/24 516 (72) Inventor Yujiro Kumagai 1-43 Minami, Yuge-cho, Yao-shi, Osaka Yamamoto Kasei Co., Ltd. (72) Inventor Denmi Misawa 1190 Kasama-cho, Sakae-ku, Yokohama-shi, Kanagawa Prefecture Inside Mitsui Chemicals Co., Ltd. (72) Inventor Taizo Nishimoto 1190 Kasama-cho, Sakae-ku, Yokohama-shi Kanagawa Prefecture Inside Mitsui Chemicals Co., Ltd. Mitsui Chemicals Co., Ltd. (72) Inventor Keisuke Takuma 1190 Kasama-cho, Sakae-ku, Yokohama-shi, Kanagawa Prefecture

Claims (5)

[Claims] 1. A dipyrromethene metal chelate compound of a dipyrromethene compound represented by the following general formula (1) and a metal ion. Embedded image [Wherein, R ₁ , R ₂ , R ₃ , R ₄ and R ₅ each independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a carboxyl group, a sulfonic acid group, a carbon number of 1 To 20 alkyl groups, halogenoalkyl groups, alkoxyalkyl groups, alkoxy groups, alkoxyalkoxy groups, aryloxy groups, dialkylaminoalkoxy groups, alkylthioalkyl groups, alkylthioalkoxy groups, acyl groups, alkoxycarbonyl groups, alkylaminocarbonyl groups, Dialkylaminocarbonyl, alkylcarbonylamino, arylcarbonylamino, arylaminocarbonyl, aryloxycarbonyl, aralkyl, aryl, arylsulfonyl, arylthio, heteroaryl, heteroaryloxy, A teloarylthio group, a heteroarylsulfonyl group, an alkylthio group, an alkenyloxycarbonyl group, an aralkyloxycarbonyl group, an alkoxycarbonylalkoxycarbonyl group, an alkylcarbonylalkoxycarbonyl group, a hydroxyalkylaminocarbonyl group, a di (hydroxyalkyl) aminocarbonyl group, It represents an alkoxyalkylaminocarbonyl group, a di (alkoxyalkyl) aminocarbonyl group or an alkenyl group having 2 to 20 carbon atoms, and A represents a substituted or unsubstituted heterocyclic ring and naphthalene ring. ] 2. The dipyrromethene metal chelate compound according to claim 1, represented by the following general formula (2). Embedded image [Wherein, R ₁ , R ₂ , R ₃ , R ₄ and R ₅ represent the same meaning as in formula (1), and M represents nickel, cobalt, iron, ruthenium, rhodium, palladium, copper, osmium, iridium, platinum Represents manganese or zinc] 3. The method according to claim 1, which is represented by the following general formula (3).
Dipyrromethene metal chelate compound. Embedded image[Wherein, R₁, R_Two, R_Three, R_FourAnd R_FiveIs the same as equation (1)
Represents the same meaning, X₁And X _TwoIs alkyl having 1 to 20 carbon atoms
Group, halogenoalkyl group, alkoxyalkyl group,
Thioalkyl groups, dialkylaminoalkyl groups,
Alkoxy group, alkoxyalkoxyalkoxy group, al
Quilthioalkoxy group, dialkylaminoalkoxy
Alkoxy group, alkylthio group, alkoxyalkylthio
O group, alkylthiocarbonylalkylthio group, dial
Killaminoalkylthio, aryloxy, aryl
Luthio, heteroaryl, heteroaryloxy
Represents a group, a heteroarylthio group and a halogen atom] 4. An optical recording medium having at least a recording layer and a reflective layer on a substrate, wherein the recording layer comprises
An optical recording medium containing the dipyrromethene metal chelate compound according to any one of the above. 5. The optical recording medium according to claim 4, wherein recording and reproduction can be performed with respect to a laser beam selected from a wavelength range of 520 to 690 nm.