JP3357153B2 - Phthalocyanine compound and optical recording medium containing the same - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compound useful as a near-infrared absorbing agent which plays an important role in optoelectronics such as information recording, display sensors, safety glasses and the like, and a recording layer containing the compound. Optical recording media such as optical disks and optical cards.

[0002]

2. Description of the Related Art A technique using a phthalocyanine dye, particularly an alkoxy-substituted phthalocyanine, in a recording layer of a recording medium such as an optical disk or an optical card is disclosed in Japanese Patent Application Laid-Open No. 61-154888.
Nos. JP186404, 61-197280, 61-246091, 62-3928
No. 6 (US Pat. No. 4,769,307), 63-3799
No. 1, JP-A-63-39388, and the like. The optical recording media using phthalocyanine dyes disclosed in these patents have not been said to have sufficient performance in sensitivity and recording characteristics. In particular, in Japanese Patent Application Laid-Open No. 61-197280, MPc (OR) _n
(Y) _16-n (M: metal, OR: alkoxy group, Y: hydrogen or halogen atom, Pc: phthalocyanine ring, n = 5
To 16), but the metal is Cu,
It is preferable to pay attention to Ni, Co, Fe, In, Al, Pt, V, hydrogen, and the like, and does not describe effects and examples of Pd. The alkoxy groups are the same in the molecule.

An improvement over the above is disclosed in Japanese Patent Laid-Open No. 3-62878.
No. 5,240,067, even the improved compound has large errors in high-speed recording and high-density recording with laser light, and is still not practically sufficient. Here, too, there is no description of the effect that the central metal of the metal phthalocyanine having eight alkoxy groups at the α-position in the phthalocyanine molecule has a good Pd, and no examples.

[0004]

Writing and reading to and from an optical recording medium is generally performed with a laser of 600 to 900 nm.
Since light is used, it is necessary to control the absorption coefficient and the refractive index of the recording material in the vicinity of the used laser oscillation wavelength and to form pits with high accuracy during writing. This is particularly important in high-speed recording and high-density recording that have been recently desired. It is also indispensable to have excellent durability.

[0005] In order to satisfy the above, the structural stability is high, the refractive index is high for light near the laser oscillation wavelength,
It is necessary to develop dyes for optical recording media having good decomposition characteristics and high sensitivity. However, the dyes for optical recording media that have been conventionally developed have the drawback that, when used in a recording medium, they have drawbacks in terms of sensitivity (C / N ratio) and recording characteristics (jitter, deviation), especially in high-speed recording and high-density recording. there were.

Accordingly, an object of the present invention is to provide an optical recording medium which improves the above-mentioned drawbacks, has high sensitivity even at the time of high-speed recording and high-density recording, has good recording characteristics, and has excellent long-term stability and light resistance. Is to supply the dye.

[0007]

Means for Solving the Problems The present inventors have conducted intensive studies to solve the above-mentioned problems, and as a result, have found a novel phthalocyanine compound represented by the following general formula (I), and have completed the present invention. Was.

That is, the present invention provides a compound represented by the following general formula (I):

[0009]

Embedded image [In the formula (I), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are each independently (a) a substituted or unsubstituted saturated group having 1 to 15 carbon atoms. Hydrocarbon group or (b) 2 carbon atoms
Represents 15 substituted or unsubstituted unsaturated hydrocarbon groups. X
¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ and X ⁸ are each independently 0R ¹ , OR ² , OR ³ , OR ⁴ , OR ⁵ , OR ⁶ , O
Represents a group substituted through an oxygen atom having 1 to 20 carbon atoms different from R ⁷ and OR ⁸ , a halogen atom or a hydrogen atom,
In addition, at least two of these are groups substituted through an oxygen atom. A phthalocyanine compound represented by
And an optical recording medium formed by containing it in a recording layer.

Particularly in the general formula (I), R ¹ , R ² , R
³ , at least two of R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are branched saturated or unsaturated hydrocarbon groups, and not all are the same hydrocarbon group; R ¹ and R ² , R ³ and R ⁴ , R ⁵ and R ^6, and R ⁷ and R ⁸ , are saturated or unsaturated hydrocarbon groups represented by different molecular formulas or different geometric structural formulas, X ¹ , X ² , X ³ , X ⁴ ,
X ⁵ , X ⁶ , X ⁷ and X ⁸ are all groups which are substituted through an oxygen atom having 1 to 20 carbon atoms, R ¹ , R ² , R ³ ,
The total number of carbon atoms of the hydrocarbon groups of R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is from 24 to 64, furthermore, R ¹ and R ² , R ³ and R ⁴ , R ⁵ and R ⁶ And the combination of R ⁷ and R ⁸ is preferably such that the sum of the number of carbon atoms of each hydrocarbon group is 6 to 16.

The substituent of the substituted saturated or unsaturated hydrocarbon group represented by the general formula (I) includes an alkyloxy group, an aryloxy group, an acyl group, a hydroxy group,
There are an amino group, an alkylthio group, an arylthio group, and an aryl group. As the unsaturated hydrocarbon group, an alkenyl group,
There are an alkynyl group and an aryl group. Examples of the group substituted through an oxygen atom include a linear, branched or cyclic C 6 to C 15 alkoxy group having 1 to 15 carbon atoms and a C 6 to C 15 cyclic alkoxy group.
20 ants - aryloxy group, an aralkyloxy group, or X ¹ and X ² having 6 to 20 carbon atoms, X ³ and X ^4, X ⁵ and X ^6, X ⁷
And X ⁸ are linked via an oxygen atom to form a cyclic oxy group.

[0012] The phthalocyanine compound of the present invention comprises 700
It has a sharp absorption at ~ 800 nm, a high molecular extinction coefficient of 150,000 or more, and is excellent in long-term stability and light resistance. It is suitable as a recording material for a recording medium (optical disk, optical card, etc.). Although the mechanism is not yet clear and is currently under investigation, the steric hindrance and melting point in the molecule were controlled by substituting the appropriate eight OR groups at the α-position of the phthalocyanine ring, and the central metal was Pd. It is considered that the fact that the appropriate absorption wavelength and absorption coefficient were obtained by the above-mentioned process contributed to the improvement of the sensitivity at the time of recording and reduced the error of the formed signal.
That is, the decomposition and melting of the dye were controlled during optical recording to form pits with high precision, damage to the resin substrate of the recording medium was reduced, and in the case of a recording medium having a reflective layer, the reflection between the recording layer and And that the adhesion to the metal layer, which is a layer, is improved. Further, by using Pd as the central metal, the heat, light and chemical stability were excellent.

The characteristics of the phthalocyanine compound of the present invention are as follows:
Eight saturated hydrocarbon groups or unsaturated hydrocarbon groups are substituted at the α-position of the phthalocyanine ring via an oxygen atom, the central metal is Pd, and at least two of the eight β-positions of the phthalocyanine ring have Is that a substituent via an oxygen atom is substituted.

Hereinafter, preferred embodiments of the present invention will be described in detail.

In the general formula (I), specific examples of the substituent represented by OR are a saturated hydrocarbon oxy group having 1 to 15 carbon atoms or an unsaturated hydrocarbon oxy group having 2 to 15 carbon atoms. Considering the availability and the melting point of the entire phthalocyanine molecule, a substituted or unsubstituted saturated or unsaturated hydrocarbon oxy group having up to 12 carbon atoms is preferable.

For example, examples of unsubstituted saturated hydrocarbonoxy groups include methoxy, ethoxy, n-propyloxy, iso-propyloxy, iso-butyloxy, sec-
Butyloxy group, tert-butyloxy group, n-pentyloxy group, iso-pentyloxy group, neo-pentyloxy group, 2-methylbutyl-3-oxy group, n-hexyloxy group, cyclo-hexyloxy group, 2-methyl Pentyl-1-oxy group, 2-methylpentyl-4-oxy group, 2-methylpentyl-5-oxy group, 2-methylpentyl-3-oxy group, 3-methylpentyl-4-oxy group, 3-methyl Pentyl-5-oxy group, n-heptyloxy group, 2-methylhexyl-5-oxy group, 2-methylhexyl-6-oxy group, 2,4-dimethylpentyl-3-oxy group, 2-methylhexyl- 3-oxy group, heptyl-4-oxy group, n-octyloxy group, 2-ethylhexyl-1-oxy group, 2,5-dimethylhexyl-3-oxy group,
2,4-dimethylhexyl-3-oxy group, 2,2,4-trimethylpentyl-3-oxy group, n-nonyloxy group, 3,5-dimethylheptyl-4-oxy group, 2,6-dimethylheptyl- 3-oxy group, 2,4-dimethylheptyl-3-oxy group, 3,5,5-trimethylhexyl-1-oxy group, n-dodecyloxy group, 2,
2,5,5-tetramethylhexyl-3-oxy group, 1-cyclo-pentyl-2,2-dimethylpropyl-1-oxy group, 1-cyclo-hexyl-2,2-dimethylpropyl-1-oxy group And the like.

Examples of the substituted saturated hydrocarbon oxy group include an alkoxyalkoxy group such as a methoxyethoxy group, an ethoxyethoxy group, a propoxyethoxy group, a butoxyethoxy group, a γ-methoxypropyloxy group and a γ-ethoxypropyloxy group, and methoxyethoxy. Ethoxy group, alkoxyalkoxyalkoxy group such as butyloxyethoxyethoxy group, dimethylaminoethoxy group, 2-amino-2-
An aminoalkoxy group such as a methylhexyl-3-oxy group,
Benzyloxy group, 4-tert-butylbenzyloxy group, 4
-cyclo-hexylbenzyloxy group, phenylethyloxy group, naphthylmethyloxy group, aralkyloxy group such as 3-benzyl-3-methylbutyl-2-oxy group,

Hydroxyalkoxy groups such as 2-hydroxyethyl-1-oxy group and 2-hydroxy-3-phenoxypropyl-1-oxy group; acyloxyalkoxy groups such as acetoxyethyloxy group and acetoxyethoxyethyloxy group; tert-butylphenoxymethoxy group, aryloxyalkoxy group such as phenoxyethoxy group, methylthioethoxy group, ethylthioethoxy group, alkylthioalkoxy group such as n-propylthiopropoxy group, phenylthiomethoxy group, naphthylthioethoxy group, 4- and arylthioalkoxy groups such as tert-butylphenylthioethoxy group and methoxyphenylthiomethoxy group.

Examples of the substituted or unsubstituted unsaturated hydrocarbonoxy groups include ethenyloxy, 2-propenyl-1-oxy, 1-butenyl-3-oxy, 2-butenyl-1-oxy, 3- Butenyl-1-oxy group, 3-butenyl-2-oxy group,
1-hydroxy-2-butenyl-4-oxy group, 2-pentenyl-1
-Oxy group, 3-pentenyl-2-oxy group, 1-pentenyl-3
-Oxy group, 1,4-pentadienyl-3-oxy group, 1-hexenyl-3-oxy group, 2-hexenyl-1-oxy group, 2-hexenyl-4-oxy group, 3-hexenyl-2-oxy group , 4-hexenyl-3-oxy group, 5-hexenyl-2-oxy group, 5-hexenyl-1-oxy group, 3-hexenyl-1-oxy group, 4-hexenyl-1-oxy group, 2,4- Hexadienyl-1-oxy group, 1,
4-hexadienyl-3-oxy group, 1,5-hexadienyl-3-
Oxy group, 1-hydroxy-2,4-hexadienyl-6-oxy group, 2,5-hexadienyl-1-oxy group, 1,3-hexadienyl-5-oxy group, 1-heptenyl-3-oxy group, 2 -Heptenyl-4-oxy group, 3-heptenyl-5-oxy group, 1,4-heptadienyl-3-oxy group, 1,5-heptadienyl-4-oxy group, 1,5-heptadienyl-3-oxy group, 2,5-heptadienyl-4-oxy group, 1-octenyl-3-oxy group, 2-octenyl-4-oxy group, 1-octenyl-4-oxy group, 1-nonenyl-3-oxy group,

4-dimethylamino-1-butenyl-3-oxy group, 4-methylthio-1-butenyl-3-oxy group, 4-acetoxy-1-butenyl-3-oxy group, 4-phenylthio-1-butenyl -3-oxy group, 1-cyclopentyl-2-methyl-2-propenyl-1-oxy group, 1-cyclohexyl-2-methyl-2-propenyl-1-oxy group, 2-methyl-2-butenyl-1- Oxy group, 3-methyl-2-butenyl-1-oxy group, 2-methyl-3-butenyl-2-oxy group, 3-methyl-3-butenyl-2-oxy group, 3-methyl-2-butenyl- 1-oxy group, 2-methyl-3-butenyl-1-oxy group, 3-methyl-3-butenyl-1-oxy group, 2,3-dimethyl-3-butenyl-2-oxy group, 2-methyl- 1
-Pentenyl-3-oxy group, 3-methyl-1-pentenyl-3-oxy group, 4-methyl-3-pentenyl-2-oxy group, 4-methyl
-1-pentenyl-3-oxy group, 3-methyl-4-pentenyl-3-
Oxy group, 2-methyl-4-pentenyl-3-oxy group, 3-methyl-4-pentenyl-2-oxy group, 4-methyl-4-pentenyl-
2-oxy group, 2-methyl-4-pentenyl-2-oxy group, 2,4-
Dimethyl-1-pentenyl-3-oxy group, 2,3-dimethyl-1-
Pentenyl-3-oxy group, 2,4-dimethyl-1,4-pentadienyl-3-oxy group, 2,4,4-trimethyl-1-pentenyl-3-
Oxy group, 4-methyl-4-hexenyl-3-oxy group, 2-methyl-1-hexenyl-3-oxy group, 2-methyl-4-hexenyl-
3-oxy group, 3-methyl-3-hexenyl-2-oxy group, 4-methyl-4-hexenyl-2-oxy group, 5-methyl-5-hexenyl-2-oxy group, 5-methyl-5- Hexenyl-3-oxy group, 2
-Methyl-5-hexenyl-3-oxy group, 2,5-dimethyl-5-hexenyl-4-oxy group, 2,5-dimethyl-5-hexenyl-3-
Oxy group, 2,2-dimethyl-5-hexenyl-3-oxy group, 2-
Methyl-1,5-hexadienyl-3-oxy group, 2-methyl-1,5
-Hexadienyl-4-oxy group, 5-methyl-1,5-hexadienyl-3-oxy group, 2,5-dimethyl-1,5-hexadienyl
-3-oxy group, 2,2-dimethyl-5-hexenyl-4-oxy group, 2,3,4-trimethyl-4-hexenyl-3-oxy group, 2-methyl-1-heptenyl-3-oxy group , 5-methyl-1-heptenyl-3-oxy group, 4-methyl-4-heptenyl-3-oxy group, 6
-Methyl-5-heptenyl-2-oxy group, 5-methyl-1-heptenyl-4-oxy group, 6-methyl-6-heptenyl-3-oxy group, 2-methyl-1,5-heptadienyl-4- Oxy group, 2,5-dimethyl-1-heptenyl-3-oxy group, 3,5-dimethyl-1,6-
Heptadienyl-4-oxy group, 2,4-dimethyl-2,6-heptadienyl-1-oxy group, 2,6-dimethyl-2,5-heptadienyl-4-oxy group, 3,5-dimethyl-1,5 -Heptadienyl-4
-Oxy group, 2-methyl-4-dimethylamino-1-butenyl-3-
Oxy group, 2-methyl-4-methylthio-1-butenyl-3-oxy group, 3-methyl-2-pentenyl-4-yn-1-oxy group, 2,6
-Dimethyl-1-nonenyl-3-yn-5-oxy group, 1-phenyl
-4-methyl-1-pentynyl-3-oxy group, 4-ethyl-1-hexynyl-3-oxy group, 2,6-dimethyl-6-heptenyl-4-yn-3-oxy group, 4-methyl- 1-pentynyl-3-oxy group, 4
-tert-butylphenyloxy group, naphthyloxy group, toluyloxy group, methoxyphenyloxy group and the like.

Particularly preferred examples are those having 11 carbon atoms in consideration of the melting point of the dye and the cyclization reaction to phthalocyanine.
In the following, those which have a moderate steric hindrance by moderately branching, and a group capable of increasing the extinction coefficient per unit weight, and a group effective for improving sensitivity when used as an optical recording medium, specifically Is iso-butyloxy group, iso-pentyloxy group, 2-methylpentyl-1-oxy group, 2-methylpentyl-5-oxy group, 3-methylpentyl-5-oxy group, 2-methylhexyl-6-oxy Group, 2-ethylhexyl-1-oxy group, 3,5,5-trimethylhexyl-1-oxy group, 2-methyl-
2-butenyl-1-oxy group, 3-methyl-2-butenyl-1-oxy group, 3-methyl-2-butenyl-1-oxy group, 2-methyl-3-
Butenyl-1-oxy group, 3-methyl-3-butenyl-1-oxy group, 2,4-dimethyl-2,6-heptadienyl-1-oxy group, 3
-Methyl-2-pentenyl-4-yn-1-oxy group, 4-tert-butylbenzyloxy group and the like. However, the general formula (I)
Of the combinations of OR ¹ and OR ² , OR ³ and OR ⁴ , OR ⁵ and OR ^6, and OR ⁷ and OR ⁸ , it is preferable that one of them is the above.

Also, OR ¹ and OR ² , OR ³ and OR ⁴ , OR
^Of the combinations of ⁵ and OR ⁶ and OR ⁷ and OR ⁸ , those having a saturated or unsaturated hydrocarbon group represented by a different molecular formula or a different geometrical structural formula are preferred because of their higher solubility in a coating organic solvent.

The following groups can be exemplified as the groups substituted through the oxygen atoms represented by X ¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ and X ⁸ . As a straight-chain, branched or cyclic C6-C15 alkoxy group having 1 to 15 carbon atoms, methoxy group, ethoxy group, n-propoxy group, iso-propoxy group, n-butoxy group, tert-butoxy group, n -Pentoxy, iso-pentoxy, neo-pentoxy, 2-methylbutyloxy, n-hexyloxy, iso-hexyloxy, neo-hexyloxy, 2-ethylbutyloxy, 3-methylpentyl Oxy group, 4-tert-butylhexyloxy group, 1,2-dimethylpropyloxy group, cyclohexyloxy group, 2-methylcyclohexyloxy group, 2,
4-dimethylcyclohexyloxy group, heptyloxy group, n-octyloxy group, n-nonyloxy group, 2-ethylhexyl-1-oxy group, n-dodecyloxy group, 3,5,5-trimethylhexyl-1-oxy group And their substituted products / derivatives. Examples of aryloxy groups having 6 to 20 carbon atoms include phenoxy, 4-tert-butylphenyloxy, 4-tert-amylphenyloxy, 2,4-
Di-iso-propylphenyloxy group, naphthyloxy group,
And their substituted products and derivatives. Examples of the aralkyloxy group having 6 to 20 carbon atoms include a benzyloxy group, a 4-tert-butylbenzyloxy group, a phenethyloxy group, a 4-cyclohexylbenzyloxy group, a naphthylmethyloxy group, and substituted products and derivatives thereof. Is mentioned. X ¹ and X ^2, X ³ and X ^4, X ⁵ and X ^6, X ⁷ and X ⁸
Are linked via an oxygen atom to form a cyclic oxy group, such as —OCH ₂ CH ₂ O—,

[0024]

Embedded image And their substituted products and derivatives.

As the halogen, fluorine, chlorine, bromine,
Iodine.

As a method for synthesizing the phthalocyanine compound represented by the general formula (I), the following formula (II)

[0027]

Embedded image [In the benzene ring in the formula (II), OR, OR ', X and X' represent a substituent as described in the aforementioned general formula (I). And reacting it with a Pd metal derivative in an alcohol by heating in the presence of, for example, 1,8-diazabicyclo [5,4,0] -7-undecene (DBU). Alternatively, a method of performing a heat reaction with a Pd metal derivative in a high boiling point solvent such as chloronaphthalene, bromonaphthalene, or trichlorobenzene may be used.

Examples of Pd metal derivatives include PdCl ₂ , P
dBr ₂ , PdI ₂ , PdO, PdSO ₄ , (CH ₃ CO
O) ₂ Pd, Pd (NO ₃ ) ₂ , (CF ₃ COO) ₂ Pd and the like. The halogen atom substitution is performed by reacting the phthalocyanine compound synthesized from the formula (II) with a halogenating agent such as thionyl chloride, sulfuryl chloride, hydrobromic acid, bromine, iodine, iodine monochloride, and copper halide. Can be. Further, a method of reacting a compound represented by the formula (II) with ammonia in alcohol using sodium methylate as a catalyst and similarly reacting a diiminoisoindoline represented by the formula (III) as an intermediate may be mentioned. .

[0029]

Embedded image

The synthesis of the compound represented by the formula (II) is generally carried out in JP-A-61-197280 and JP-A-02-27.
It can be synthesized by the methods described in JP-A-9664 and JP-A-02-279665.

In a method for producing an optical recording medium using the phthalocyanine compound of the present invention, one or two layers of one to three kinds of compounds containing the phthalocyanine compound of the present invention are coated or vapor-deposited on a transparent substrate. There is a coating method, and as a coating method, the binder resin is 20% by weight or less, preferably 0% by weight.
% Of the phthalocyanine compound of the present invention is 0.05 to 20% by weight, preferably 0.5 to 20% by weight, and is applied by a spin coater. In addition, as a deposition method, 10 ^-5 to 10 ^-7 torr, 100 to
At 300 ° C., a substrate containing a phthalocyanine compound
There is a method of depositing three kinds of compounds.

The substrate may be any optically transparent resin. For example, acrylic resin, polyethylene resin, vinyl chloride resin, vinylidene chloride resin, polycarbonate resin, polyolefin copolymer resin, vinyl chloride copolymer resin, vinylidene chloride copolymer resin, styrene copolymer resin and the like can be mentioned. The substrate may be subjected to a surface treatment with a thermosetting resin or an ultraviolet curable resin.

When an optical recording medium (optical disk, optical card, etc.) is manufactured, a polyacrylate substrate or a polycarbonate substrate is used as the substrate, and the substrate is applied by a spin coating method in terms of cost and handling of the user. preferable.

From the viewpoint of the solvent resistance of the substrate, solvents used for spin coating include halogenated hydrocarbons (eg, dichloromethane, chloroform, carbon tetrachloride, tetrachloroethylene, dichlorodifluoroethane, etc.), and ethers (eg, tetrahydrofuran, diethyl ether, Propyl ether, dibutyl ether, dioxane, etc.), alcohols (eg, methanol, ethanol, propanol, etc.), cellosolves (eg, methyl cellosolve,
Ethyl cellosolve, etc.), hydrocarbons (eg, hexane, cyclohexane, ethylcyclohexane, cyclooctane, dimethylcyclohexane, octane, benzene, toluene, xylene, etc.), or a mixed solvent thereof are preferably used.

For processing as a recording medium, a substrate covered with a substrate as described above, or a substrate provided with two recording layers,
There is a method in which an air gap is provided so as to be opposed to each other, or a reflective layer (aluminum or gold) is provided on the recording layer, and a protective layer of a thermosetting or photocurable resin is laminated. Al ₂ O ₃ , SiO ₂ , S
Inorganic compounds such as iO and SnO ₂ may be used.

[0036]

EXAMPLES The present invention will be described below in more detail with reference to examples, but embodiments of the present invention are not limited thereto.

Example 1 85.3 g (0.37 mol) of 2,3-dicyano-5,6-dichlorohydroquinone represented by the following structural formula (A-1)

[0038]

Embedded image 205.5 g (1.40 mol) of potassium carbonate and 300 ml of N, N-dimethylacetamide are charged into a vessel equipped with a stirrer, a reflux condenser and a nitrogen inlet tube, and the mixture is stirred under nitrogen aeration. After heating to 60 ° C. and stirring for 30 minutes, 124.0 g (0.82 mol) of iso-amyl bromide was added at 60 ° C., followed by heating and stirring at 80 ° C. for 20 hours.
Next, this was discharged into 1.5 liters of water, extracted and concentrated with ethyl acetate, and then purified by column (silica gel 500).
g, solvent: hexane: ethyl acetate = 5: 2) to obtain 103.0 g (yield: 75%) of an alkoxyphthalonitrile compound represented by the following structural formula (A-2).

[0039]

Embedded image

The result of purity analysis by liquid chromatography was 99.2%. The results of the elemental analysis are as follows.

[0041]

49.0 g of p-isopropylphenol
(0.36 mol), 99.5 g of potassium carbonate (0.72 mol)
Mol) and 300 ml of N, N-dimethylformamide are charged into a vessel equipped with a stirrer, a reflux condenser and a nitrogen inlet tube, and stirred under a stream of nitrogen. After heating to 60 ° C. and stirring for 30 minutes, 55.4 g (0.15 mol) of compound (A-2)
Was added at 60 ° C., and then the mixture was heated and stirred at 80 ° C. for 20 hours. Then drain it into 1.5 liters of water,
After extraction and concentration using ethyl acetate, column purification (silica gel 400 g, solvent toluene) was performed, and the following structural formula (A-
79.3 g (yield 93%) of the compound represented by 3) was obtained.

[0043]

Embedded image

The result of purity analysis by liquid chromatography was 98.9%. The results of the elemental analysis are as follows.

[0045]

Next, 17.1 g of compound (A-3) (0.1 g) was placed in a vessel equipped with a stirrer, a reflux condenser and a nitrogen inlet tube.
03 mol), 4.56 g (0.03 mol) of DBU and n
40 ml of amyl alcohol were charged and heated to 100 ° C. under a nitrogen atmosphere. Next, 1.35 g (0.0075 mol) of palladium chloride was added at the same temperature,
The reaction was carried out at １００100 ° C. for 20 hours. After the completion of the reaction, the mixture was cooled and insolubles were removed by filtration. After the filtrate was concentrated under reduced pressure to recover the solvent, the residue was purified by column (silica gel 200 g, solvent: toluene: hexane = 1: 9) to obtain green crystals of the target phthalocyanine palladium compound. Yield 7.3
g (yield 41%). The result of the purity measurement by high performance liquid chromatography was 99.0%. The results of the visible absorption spectrum and the elemental analysis are as follows.

Visible absorption: λ _max = 722.5 nm ε _g = 1.0 × 10 ⁵ cm ² g ^-1 (solvent: toluene)

A solution of the above phthalocyanine compound in n-octane (10 g / l) was added to a spiral groove (pitch 1.
A spin-coat film was formed at 500 to 1000 rpm on a CD-R polycarbonate substrate having an outer diameter of 120 mm and a thickness of 1.2 mm with a thickness of 6 μm, a groove width of 0.6 μm, and a groove depth of 0.18 μm). A reflective layer is formed by sputtering and depositing 30 nm of gold thereon, followed by overcoating with a photocurable polyacrylic resin and photocuring to form a protective layer.
A mold medium was prepared. An error rate of less than 0.2% when writing an EFM signal at a linear velocity of 1.4 m / s at a power of 6.0 mW using a semiconductor laser having a wavelength of 780 nm on this medium is less than 0.2%. Light 63 ° C, 200
There was no change in the time endurance test.

Example 2 170.6 g (0.74 mol) of the compound represented by (A-1), 205.5 g (1.40 mol) of potassium carbonate and
600 ml of N, N-dimethylformamide is charged into a vessel equipped with a stirrer, a reflux condenser and a nitrogen inlet tube, and stirred under nitrogen. After heating to 60 ° C and stirring for 30 minutes, iso-
109.6 g (0.80 mol) of butyl bromide was added to 60
C., and the mixture was heated and stirred at 80.degree. C. for 20 hours. Next, this was discharged into 3.0 liters of water, extracted and concentrated with ethyl acetate, and then purified by column (silica gel 1).
kg, solvent: hexane: ethyl acetate = 5: 2) to obtain 172.0 g (yield 81%) of an alkoxyphthalonitrile compound represented by the following structural formula (A-4).

[0050]

Embedded image

The result of purity analysis by liquid chromatography was 99.1%. The results of the elemental analysis are as follows.

[0052]

95.0 g of the compound represented by (A-4)
(0.33 mol) and 92.0 g of potassium carbonate (0.63 mol)
Mol) and N, N-dimethylacetamide (300 ml) were charged into a vessel equipped with a stirrer, a reflux condenser and a nitrogen inlet tube, and the mixture was stirred under a stream of nitrogen. After heating to 60 ° C. and stirring for 30 minutes, 61.7 g of n-hexyl bromide (0.37 g) was added.
Mol) is added at 60 ° C. and then the temperature is raised to 80 ° C. for 20 minutes.
The mixture was heated and stirred for an hour. Next, this was discharged into 1.5 liters of water, extracted and concentrated with ethyl acetate, and then purified by column (500 g of silica gel, solvent; hexane: ethyl acetate =
5: 2) to obtain 103.0 g (yield 84%) of an alkoxyphthalonitrile compound represented by the following structural formula (A-5).

[0054]

Embedded image

The result of purity analysis by liquid chromatography was 99.3%. The results of the elemental analysis are as follows.

[0056]

27.4 g of 4-tert-butylcatechol
(0.17 mol), 84.8 g (0.51 g) of potassium carbonate
Mol) and 300 ml of N, N-dimethylformamide are charged into a vessel equipped with a stirrer, a reflux condenser and a nitrogen inlet tube, and stirred under a stream of nitrogen. After heating to 60 ° C. and stirring for 30 minutes, 55.4 g (0.15 mol) of compound (A-5)
Was added at 60 ° C., and then the mixture was heated and stirred at 80 ° C. for 20 hours. Then drain it into 1.5 liters of water,
After extraction and concentration using ethyl acetate, column purification (silica gel 400 g, solvent toluene) was performed, and the following structural formula (A-
79.3 g (yield 93%) of the compound represented by 6) was obtained.

[0058]

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The result of purity analysis by liquid chromatography was 98.9%. The results of the elemental analysis are as follows.

[0060]

Next, in a vessel equipped with a stirrer, a reflux condenser and a nitrogen inlet tube, 11.1 g of compound (A-6) (0.1 g) was added.
03 mol), 4.56 g (0.03 mol) of DBU and n
40 ml of amyl alcohol were charged and heated to 100 ° C. under a nitrogen atmosphere. Next, 1.35 g (0.0075 mol) of palladium chloride was added at the same temperature,
The reaction was carried out at １００100 ° C. for 20 hours. After the completion of the reaction, the mixture was cooled and insolubles were removed by filtration. After the filtrate was concentrated under reduced pressure to recover the solvent, the residue was purified by column (silica gel 200 g, solvent: toluene: hexane = 1: 9) to obtain green crystals of the target phthalocyanine palladium compound. The yield is 6.3
g (43% yield). The result of the purity measurement by high performance liquid chromatography was 99.0%. The results of the visible absorption spectrum and the elemental analysis are as follows.

Visible absorption: λ _max = 722.0 nm ε _g = 1.4 × 10 ⁵ cm ² g ^-1 (solvent: toluene)

The dibutyl ether of the above phthalocyanine compound
A tellurium solution (10 g / l) was applied to a polycarbonate substrate for CD-R by a spin coater in the same manner as in Example 1, gold was sputter-deposited thereon, and then a protective layer was formed using a UV curable resin. And a CD-R type medium.
The error rate when writing an EFM signal with a power of 6.0 mW at a linear velocity of 1.4 m / s using a 780 nm semiconductor laser at a linear velocity of 1.4 m / s is less than 0.2%.
There was no change even when reproduction was performed 1 million times with the reproduction light of 5 mW. There was no problem in recording / reproducing even after 1000 hours at 80 ° C./85%.

Example 3 In the same manner as in Example 2, the compound of the formula (A-4) 95.
0 g (0.33 mol) and 92.0 g of potassium carbonate (0.
63 mol) and 300 ml of N, N-dimethylacetamide are charged into a vessel equipped with a stirrer, a reflux condenser and a nitrogen inlet tube, and stirred under nitrogen. After heating to 60 ° C. and stirring for 30 minutes, 55.9 g of iso-amyl bromide (0.
(37 mol) was added at 60 ° C., then the temperature was raised and the mixture was heated and stirred at 80 ° C. for 20 hours. Next, this was discharged into 1.5 liters of water, extracted and concentrated with ethyl acetate, and then subjected to column purification (500 g of silica gel, solvent: hexane: ethyl acetate = 5: 2) to give the following structural formula (A-7) 97.0 g (yield 82%) of the alkoxyphthalonitrile compound represented by the formula (1) was obtained.

[0065]

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The result of purity analysis by liquid chromatography was 99.4%. The results of the elemental analysis are as follows.

[0067]

25.9 g of 4-iso-propylcatechol
(0.17 mol), 84.8 g (0.51 g) of potassium carbonate
Mol) and 300 ml of N, N-dimethylformamide are charged into a vessel equipped with a stirrer, a reflux condenser and a nitrogen inlet tube, and stirred under a stream of nitrogen. After heating to 60 ° C. and stirring for 30 minutes, 53.3 g (0.15 mol) of compound (A-7)
Was added at 60 ° C., and then the mixture was heated and stirred at 80 ° C. for 20 hours. Then drain it into 1.5 liters of water,
After extraction and concentration using ethyl acetate, column purification (silica gel 400 g, solvent toluene) was performed, and the following structural formula (A-
55.4 g (yield: 85%) of the compound represented by 8) was obtained.

[0069]

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The result of purity analysis by liquid chromatography was 99.0%. The results of the elemental analysis are as follows.

[0071]

Next, compound (A-8) was prepared in the same manner as in Example 1.
By heating and reacting 13.0 g (0.03 mol) of palladium chloride, green crystals of the target phthalocyanine palladium compound were obtained. The yield was 5.5 g (40 yield).
%)Met. The result of the purity measurement by high performance liquid chromatography was 98.9%. The results of the visible absorption spectrum and the elemental analysis are as follows.

Visible absorption: λ _max = 722.0 nm ε _g = 1.4 × 10 ⁵ cm ² g ^-1 (solvent: toluene)

10 g of the above phthalocyanine compound was dissolved in 500 ml of a 3: 1 (volume ratio) mixed solvent of dibutyl ether and diisopropyl ether, and 100 nm thick on a polycarbonate optical card substrate by a spin coater.
Then, a protective layer was formed on the application surface using a UV-curable resin to prepare an optical card. This medium has 780n
m, the linear velocity was 2 m / s, and the CN ratio was 61 dB when recorded with a semiconductor laser beam having a linear velocity of 4 mW. In addition, linear velocity 2
m / s, laser 0.8 mW - renewable by light, were examined reproduction light stability was possible 10 ⁵ times of the playback. Further, this light card had good storage stability.

Example 4 The same procedure as in Example 1 was carried out except that 158.4 g of 2-ethylhexyl bromide was used instead of 124.0 g of iso-amyl bromide, and the alkoxyphthalonitrile represented by the following structural formula (A-9) was used. 122.5 g of compound (yield 7
3%).

[0076]

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The result of purity analysis by liquid chromatography was 99.2%. The results of the elemental analysis are as follows.

[0078]

Catechol 18.7 g (0.17 mol),
84.8 g (0.51 mol) of potassium carbonate and 300 ml of N, N-dimethylformamide are charged into a vessel equipped with a stirrer, a reflux condenser and a nitrogen inlet tube, and the mixture is stirred under nitrogen. After heating to 60 ° C. and stirring for 30 minutes, the compound (A-
9) 53.3 g (0.15 mol) was added at 60 ° C, and then the temperature was raised and the mixture was heated and stirred at 80 ° C for 20 hours. Next, this was discharged into 1.5 liters of water, extracted and concentrated with ethyl acetate, and then subjected to column purification (400 g of silica gel, toluene as a solvent) to give 64.8 g of a compound represented by the following structural formula (A-10). (88% yield).

[0080]

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The result of purity analysis by liquid chromatography was 99.0%. The results of the elemental analysis are as follows.

[0082]

After 0.58 g (0.025 mol) of metallic sodium was added to 100 ml of dehydrated methanol to completely dissolve, 24.5 g (0.05 mol) of compound (A-10) was added, and the mixture was added at 50 to 60 ° C. The heating reaction was performed while blowing ammonia gas for about 10 hours. After methanol was distilled off from the reaction solution, 200 ml of toluene was added, and then the toluene layer was washed with water. After further concentration under reduced pressure, n
-By recrystallization in hexane, the following structural formula (A-
21. Diiminoisoindoline compound represented by 11).
4 g (91% yield) were obtained.

[0084]

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The result of purity analysis by liquid chromatography was 99.0%. The results of the elemental analysis are as follows.

[0086]

Next, 15.2 g of the compound (A-11) was placed in a container equipped with a stirrer, a reflux condenser and a nitrogen inlet tube.
(0.03 mol), 2.28 g (0.015 mol) of DBU and 40 ml of n-octanol were charged and heated to 190 ° C. under a nitrogen atmosphere. Next, 1.35 g (0.0075 mol) of palladium chloride was added at the same temperature,
The reaction was performed at 185 to 195 ° C for 4 hours. After the completion of the reaction, the mixture was cooled to room temperature, discharged into 1 liter of methanol, and the precipitate was filtered. The precipitate was purified by column (silica gel 200).
g, solvent; toluene: hexane = 1: 9) to obtain green crystals of the desired phthalocyanine palladium compound. The yield was 5.3 g (34% yield). The result of purity measurement by high performance liquid chromatography was 99.1%. The results of the visible absorption spectrum and the elemental analysis are as follows.

Visible absorption: λ _max = 727.0 nm ε _g = 0.9 × 10 ⁵ cm ² g ⁻¹ (solvent: toluene)

A solution of the above phthalocyanine compound in ethylcyclohexane (20 g / l) was applied on a polycarbonate substrate for CD-R by a spin coater in the same manner as in Example 1, and gold was sputter-deposited on the polycarbonate substrate. Was used to form a protective layer to produce a CD-R type medium. The error rate when writing an EFM signal with a power of 6.0 mW at a linear velocity of 2.8 m / s using a 780 nm semiconductor laser on this medium is less than 0.2%,
There was no change even when reproduction was performed a million times with a reproduction light of 0.5 mW. There was no problem in recording / reproducing even after 1000 hours at 80 ° C./85%.

Example 5 A mixture of the alkoxyphthalonitrile compounds represented by the structural formulas (A-3) and (A-10) at a molar ratio of 1: 1 was mixed with palladium chloride in the same manner as in Example 1. To obtain green crystals of the desired phthalocyanine palladium compound. The yield was 5.9 g (45% yield). In addition, it was confirmed by liquid chromatography and FD-MS spectrum measurement that five or more kinds of phthalocyanine compounds were contained (α-substituted alkoxy group portion was iso-amyloxy and 2 or more).
-Ethylhexyloxy includes those having different mixing ratios. ). The results of the visible absorption spectrum and the elemental analysis are as follows.

Visible absorption: λ _max = 724.5 nm ε _g = 1.0 × 10 ⁵ cm ² g ⁻¹ (solvent: toluene)

Using the above phthalocyanine compound, a CD-R type medium was produced in the same manner as in Example 1. Using a laser having a wavelength of 780 nm for this medium, a linear velocity of 1.4 m
The error rate when writing the EFM signal at a power of 6.0 mW at / s was less than 0.2%.

Example 6 85.3 g of 2,3-dicyano-5,6-dichlorohydroquinone
In place of, 59.2 g of 2,3-dicyanohydroquinone represented by the following structural formula (A-12) was used as a raw material,

[0094]

Embedded image The same operation as in Example 2 was performed except that 154.5 g of 2-ethylhexyl bromide was used instead of 109.6 g of iso-butyl bromide, and 149.1 g of an alkoxyphthalonitrile compound represented by the following structural formula (A-13)
(74% yield).

[0095]

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The result of purity analysis by liquid chromatography was 99.0%. The results of the elemental analysis are as follows.

[0097]

89.9 g of the compound represented by (A-13) is used instead of 95.0 g of the compound represented by (A-4), and 40.3 g of ethyl bromide is used instead of 61.7 g of n-hexyl bromide. Except for the above, the same operation as in Example 2 was performed, and 84.3 g of an alkoxyphthalonitrile compound represented by the following structural formula (A-14) (yield: 85%)
I got

[0099]

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The result of purity analysis by liquid chromatography was 99.3%. The results of the elemental analysis are as follows.

[0101]

The structural formulas (A-3) and (A-1)
The alkoxyphthalonitrile compound represented by 4) is
The mixture mixed at a molar ratio of 1 was heated and reacted with palladium chloride in the same manner as in Example 1 to obtain green crystals of the target phthalocyanine palladium compound. The yield was 5.3 g (38% yield). In addition, it was confirmed by liquid chromatography and FD-MS spectrum measurement that four or more types of phthalocyanine compounds were contained. And those in which all eight β-positions were unsubstituted were not included.) The results of the visible absorption spectrum and the elemental analysis are as follows.

Visible absorption: λ _max = 723.5 nm ε _g = 1.3 × 10 ⁵ cm ² g ⁻¹ (solvent: toluene)

Using the above phthalocyanine compound, a CD-R type medium was produced in the same manner as in Example 1. Using a laser having a wavelength of 780 nm for this medium, a linear velocity of 1.4 m
The error rate when writing the EFM signal at a power of 6.0 mW at / s was less than 0.2%.

Example 7 2.0 g (1.08 mmol) of the phthalocyanine palladium compound obtained in Example 6 was dissolved in 15 ml of 1,1,2-trichloroethane, and 10 ml of water was added. Next, a mixed solution of 0.71 g (4.43 mmol) of bromine and 2 ml of 1,1,2-trichloroethane was added dropwise at 50 to 55 ° C.
The mixture was reacted at ６０60 ° C. for 4 hours, and washed by adding 3 g of a 15% aqueous sodium sulfite solution. The organic layer was treated with methanol 150
The resulting solution was added dropwise to the resulting solution, and the precipitated crystals were filtered. Further, the crystals were subjected to column purification (100 g of silica gel, solvent of toluene) to obtain 2.1 g of the desired phthalocyanine compound (yield: 90%).
%).

The result of purity analysis by high performance liquid chromatography was 98.9%. The results of the visible absorption spectrum and the elemental analysis are as follows.

Visible absorption: λ _max = 726.5 nm ε _g = 1.1 × 10 ⁵ cm ² g ^-1 (solvent: toluene)

Using the above phthalocyanine compound, a CD-R type medium was produced in the same manner as in Example 1. Using a laser having a wavelength of 780 nm for this medium, a linear velocity of 1.4 m
The error rate when writing the EFM signal at a power of 6.0 mW at / s was less than 0.2%.

Example 8 2.0 g (1.08 mmol) of the phthalocyanine palladium compound obtained in Example 6 was dissolved in 15 ml of 1,1,2-trichloroethane, and 10 ml of water was added. Next, a mixed solution of 0.32 g (2.27 mmol) of sulfuryl chloride and 2 ml of 1,1,2-trichloroethane was added dropwise at 55 to 55 ° C, and reacted at 65 to 70 ° C for 1 hour. The organic layer was dropped into 150 ml of methanol, and the precipitated crystals were filtered.
The crystals were further purified by column (100 g of silica gel, solvent toluene) to obtain 1.8 g of the target phthalocyanine compound.
(85% yield).

The result of purity analysis by high performance liquid chromatography was 99.0%. The results of the visible absorption spectrum and the elemental analysis are as follows.

Visible absorption: λ _max = 723.0 nm ε _g = 1.3 × 10 ⁵ cm ² g ^-1 (solvent: toluene)

A CD-R type medium was produced in the same manner as in Example 1 using the above phthalocyanine compound. Using a laser having a wavelength of 780 nm for this medium, a linear velocity of 1.4 m
The error rate when writing the EFM signal at a power of 6.0 mW at / s was less than 0.2%.

Example 9 A mixture of the alkoxyphthalonitrile compounds represented by the structural formulas (A-2) and (A-6) at a molar ratio of 1: 1 was mixed with palladium chloride in the same manner as in Example 1. To give green crystals of the desired phthalocyanine palladium compound. The yield was 6.1 g (yield 45
%)Met.

Note that liquid chromatography and FD-M
It was confirmed by S spectrum measurement that four kinds of phthalocyanine compounds were contained (the number of Cl was 0, 2,
Contains 4, 6 phthalocyanines. ). The results of the visible absorption spectrum and the elemental analysis (Cl = 4) are as follows.

Visible absorption: λ _max = 721.5 nm ε _g = 1.5 × 10 ⁵ cm ² g ^-1 (solvent: toluene)

Using the above phthalocyanine compound, a CD-R type medium was produced in the same manner as in Example 1. Using a laser having a wavelength of 780 nm for this medium, a linear velocity of 1.4 m
The error rate when writing the EFM signal at a power of 6.0 mW at / s was less than 0.2%.

Example 10 23.2 g (0.17 mol) of p-isopropylphenol, 99.5 g (0.72 mol) of potassium carbonate and N,
300 ml of N-dimethylformamide is charged into a vessel equipped with a stirrer, a reflux condenser and a nitrogen inlet tube, and the mixture is stirred under nitrogen. After heating to 60 ° C. and stirring for 30 minutes, 55.4 g (0.15 mol) of compound (A-2) was added at 60 ° C., followed by heating and stirring at 80 ° C. for 20 hours. Next, this was discharged into 1.5 liters of water, extracted and concentrated using ethyl acetate, and then column purified (400 g of silica gel,
Solvent toluene) to obtain 56.3 g (yield: 80%) of a compound represented by the following structural formula (A-15).

[0118]

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The result of purity analysis by liquid chromatography was 98.9%. In addition, as a result of FD-MS measurement, most contained one Cl in the molecule. The results of the elemental analysis are as follows.

[0120]

The alkoxyphthalonitrile compound represented by A-15 was heated and reacted with palladium chloride in the same manner as in Example 1 to obtain the desired green crystal of the phthalocyanine palladium compound. The yield was 6.4 g (43% yield). In addition, the result of purity analysis by liquid chromatography was 99.1%. The results of the visible absorption spectrum and the elemental analysis are as follows.

Visible absorption: λ _max = 722.0 nm ε _g = 1.3 × 10 ⁵ cm ² g ^-1 (solvent: toluene)

Using the above phthalocyanine compound, a CD-R type medium was produced in the same manner as in Example 1. Using a laser having a wavelength of 780 nm for this medium, a linear velocity of 1.4 m
The error rate when writing the EFM signal at a power of 6.0 mW at / s was less than 0.2%.

Examples 11 to 23 Reaction of 1 to 4 kinds of diiminoisoindolines derived from phthalonitrile (Table 1) or (II) represented by the following general formula (II) with a Pd metal derivative. By
The phthalocyanines shown in Table 2 were synthesized. These compounds had large extinction coefficients.

[0125]

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A dimethylcyclohexane solution (10 g / l) of each of these phthalocyanine compounds was applied to an optical card substrate made of PMMA to a thickness of 100 nm by a spin coater, and then a protective layer was formed on the application surface using a UV curable resin. The optical card was produced. These optical cards are 78
Recording can be performed with a semiconductor laser beam of 0 nm, a linear velocity of 2 m / s and 4 mW, and the CN ratio at that time is 58 to 61.
dB. The linear velocity 2m / sec, can be reproduced by a laser beam of 0.8 mW, it was possible to 10 ^five regeneration was examined reproduction light stability. Further, CD was prepared in the same manner as in Example 1 using each of the above phthalocyanine compounds.
-An R type medium was produced. These media have a wavelength of 780n.
The error rate when writing an EFM signal at a linear velocity of 1.4 m / s with a power of 6.0 mW using a m laser was less than 0.2%. Further, when a light resistance test was performed on these media using a xenon lamp at 50 ° C.,
There was no change after 00 hours.

[0127]

[Table 1]

[0128]

[Table 2]

Comparative Test The performance of the optical recording medium of the phthalocyanine compound obtained above and that of the optical recording medium using a known phthalocyanine compound were compared. Examples 1 and 2
2,3,7,10,12,13,15,18,20,2
Using media prepared in the same manner as in Example 1 using the compounds of Nos. 6, 27 and 28, the following two types of known alkoxyphthalocyanines (exemplified compounds of JP-A-3-62878 (USP5124067)) were used as comparative examples. A medium prepared in the same manner as in Example 1 was used.

Comparative Example 1:

[0131]

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Comparative Example 2:

[0133]

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Recording and reproduction were performed at a laser wavelength of 780 nm, and recording was performed using the following three methods. Normal recording: Information of 63 minutes is recorded at a linear velocity of 1.4 m / s (1 × speed). High-speed recording: Information of 63 minutes is recorded at a linear velocity of 5.6 m / s (4 times speed). High-density recording: Information of 74 minutes is recorded at a linear velocity of 1.2 m / s.

In the case of normal recording and high-density recording, 6.
Recording was performed with a laser power of 0 mW and 8.0 mW during high-speed recording.

Further, the recording sensitivity (C / N ratio), jitter and deviation are each set to the CD decoder DR35.
52 (manufactured by Kenwood), LJM-1851 jitter meter (manufactured by Reader Electronics) and TIA-175 time interval analyzer (manufactured by ADC). Table 3 shows the evaluation results.

[0137]

[Table 3]

Evaluation Criteria Sensitivity (C / N ratio): ≧ 55 dB ×: <55 dB Jitter ：: <35 pit jitter and 3T land jitter <35
ns ×: 3T pit jitter or 3T land jitter ≧ 35
ns deviation ○: -50 ns <3T and 11T deviation <50
ns ×: 3T or 11T deviation ≧ 50 ns or 3T or 11T deviation ≦ −50 ns From the results in Table 3, the effect of the present invention is clear.

[0139]

The phthalocyanine compound of the present invention has a group in which the α-position of the phthalocyanine ring is substituted with eight suitable alkoxy groups via an oxygen atom, and the β-position is substituted via an oxygen atom different from the α-position. However, the central metal is Pd. In the optical recording medium using this compound, the decomposition and melting of the dye at the time of writing could be controlled, so that sensitivity and recording characteristics in high-speed recording and high-density recording as well as ordinary recording were improved.

──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Taizo Nishimoto 1190 Kasama-cho, Sakae-ku, Yokohama-shi, Kanagawa Prefecture Inside Mitsui Toatsu Chemical Co., Ltd. Within Chemical Co., Ltd. (72) Inventor Naoto Ito 1190 Kasama-cho, Sakae-ku, Yokohama-shi, Kanagawa Prefecture Within Mitsui Toatsu Chemical Co., Ltd. (58) Field surveyed (Int.Cl. ⁷ , DB name) 26 C09B 47/18 G11B 7/24 516 CA (STN) REGISTRY (STN)

Claims (7)

(57) [Claims] 1. A compound represented by the following general formula (I) [In the formula (I), R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are each independently (a) a substituted or unsubstituted saturated group having 1 to 15 carbon atoms. Hydrocarbon group or (b) 2 carbon atoms
Represents 15 substituted or unsubstituted unsaturated hydrocarbon groups. X
¹ , X ² , X ³ , X ⁴ , X ⁵ , X ⁶ , X ⁷ and X ⁸ are each independently 0R ¹ , OR ² , OR ³ , OR ⁴ , OR ⁵ , OR ⁶ , O
Represents a group substituted through an oxygen atom having 1 to 20 carbon atoms different from R ⁷ and OR ⁸ , a halogen atom or a hydrogen atom,
In addition, at least two of these are groups substituted through an oxygen atom. A phthalocyanine compound represented by the formula: 2. The method according to claim 1, wherein R ¹ , R ² , R ³ ,
A phthalocyanine compound in which at least two of R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are a branched saturated or unsaturated hydrocarbon group, and not all are the same hydrocarbon group. 3. The combination according to claim 2, wherein the combination of R ¹ and R ² , R ³ and R ⁴ , R ⁵ and R ^6, and R ⁷ and R ⁸ represents a different saturated or saturated structure represented by a different molecular formula or a different geometric structural formula. A phthalocyanine compound that is an unsaturated hydrocarbon group. 4. The method according to claim 1, wherein X ¹ , X ² , X ³ ,
A phthalocyanine compound in which X ⁴ , X ⁵ , X ⁶ , X ⁷ and X ⁸ are all groups substituted through an oxygen atom having 1 to 20 carbon atoms. 5. The method according to claim 1, wherein R ¹ , R ² , R ³ ,
A phthalocyanine compound in which the total number of carbon atoms in the hydrocarbon groups of R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ is from 24 to 64. 6. A combination of R ¹ and R ² , R ³ and R ⁴ , R ⁵ and R ^6, and R ⁷ and R ⁸ , wherein the sum of carbon numbers of each hydrocarbon group is 6 to 6. 16. A phthalocyanine compound which is 16. 7. An optical recording medium formed by containing the phthalocyanine compound according to claim 1, 2, 3, 4, 5, or 6 in a recording layer.