JPH0890922A - Compact disk or compact disk-rom corresponding write-once optical disk - Google Patents

Abstract

PURPOSE: To improve solubility, an attenuation coefficient, optical reflectivity and light fastness by using coloring matter composed of a specific compd. satisfying physical property values required as org. coloring matter for a CD or CD- ROM corresponding write-once optical disk, and forming a recording film from the coloring matter. CONSTITUTION: A CD or CD-ROM corresponding write-once optical disk is constituted of a transparent substrate, a recording film and a reflecting film. As the transparent substrate, a polycarbonate resin is pref. used. As the reflecting film, gold, silver, platinum or aluminum is used. As the coloring matter for the recording film used in this write-once optical disk, a compd. represented by the general formula (wherein OR<1> is bonded to the fourth position 4 or 4' of each of respective benzene nuclei and R<1> is a 4 or more C alkyl group and a plurality of R<1> -groups may be respectively same or different and R<2> is a 4-7C alkyl group and a plurality of R<2> -groups may be respectively same or different) is used.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a compact disc (CD) compatible or CD-ROM compatible write-once optical disc, and more specifically to a recording film dye used in a CD-compatible or CD-ROM compatible write-once optical disc. The present invention relates to a write-once type optical disc compatible with a CD or a CD-ROM used.

[0002]

2. Description of the Related Art A write-once type optical disk compatible with a CD or a CD-ROM is generally composed of a transparent substrate / recording film / reflection film. The spin coating method is adopted for the formation of the recording film because of its manufacturing cost advantage, and the dye as the recording film is required to have solubility in a solvent that does not damage the substrate. Normal,
Solubility of 2 to 3% by weight or more is required to obtain a good film-forming state. In addition, since it can be reproduced by a commercially available CD player and compatibility with a CD-ROM is required, the recording film has an optical reflectance of 70% or more (in the wavelength range of 770 to 790 nm) when laminated with the reflection film. Required to have. Therefore, if the extinction coefficient of the dye film is too large, a reflectance of 70% or more cannot be obtained, and conversely, if it is too small, the recording sensitivity is significantly reduced. Therefore, a dye film having an extinction coefficient within a certain range is required. To be done. Usually, it is about 0.05 to 0.2. Polycarbonate resin is mainly used as the transparent substrate because of its good physical properties and low price, and gold is used as the reflective film because of its stability and high reflectance.

A phthalocyanine dye having a phosphate as an axial ligand is described in JP-A-4-214388. However, in the compound of the formula [I] of the publication, for example, an alkyl group of OR ¹ bonded to a benzene nucleus of a phthalocyanine compound, an alkoxy group of R ¹¹ , R ¹² , R ²² and R ²³ in a phosphoric acid ester group. There is no limit to the number of carbons in. As a practical matter, when the number of carbon atoms of the alkoxy group is 3 or less or 8 or more, the extinction coefficient does not satisfy the required value, and it is CD compatible or CD.
-Cannot be used as a write-once optical disc for ROM.
If the alkoxy group or the alkyl group has 3 or less carbon atoms, the solubility of the dye becomes about 1% by weight,
It cannot be used as a recording film. Unless the carbon numbers of these alkoxy groups and alkyl groups are specified in this way, it is not possible to satisfy all the physical property values required for the dye of the recording film.

[0004]

DISCLOSURE OF THE INVENTION The object of the present invention is to provide a CD
An organic dye for a write-once type optical disc compatible with or compatible with a CD-ROM, which provides a dye satisfying required physical property values and uses the dye as a recording film for a CD or a CD-ROM.
It is to provide a corresponding write-once optical disc.

[0005]

That is, the present invention is based on the general formula (1)

[0006]

[Chemical 3]

(In the formula, OR ¹ is bonded to the 4-position or 4'-position of each benzene nucleus, R ¹ is an alkyl group having 4 or more carbon atoms, and a plurality of R ¹ are the same or different. R ² is an alkyl group having 4 to 7 carbon atoms,
A plurality of R ^2's may be the same or different, and the compound represented by the formula (1) corresponds to CD or C
D-ROM compatible write-once optical disc, and

A dye for a recording film, which is composed of the compound represented by the general formula (1) and is used for a CD-compatible or CD-ROM-compatible write-once optical disc. Note that R
OM is an abbreviation for read-only memory.

In the compound represented by the general formula (1),
It is necessary that OR ¹ be bonded to the 4th or 4'position of each benzene nucleus. It is extremely difficult to synthesize at other positions. R ¹ is an alkyl group having 4 or more carbon atoms, which may have a branch, preferably 4 to 10, and examples thereof include various butyl groups (n-butyl group, isobutyl group, sec.
-Butyl group or tert-butyl group), various pentyl groups,
These are various hexyl groups, various heptyl groups, various octyl groups, various nonyl groups or various decyl groups. A plurality of R ¹ may be the same or different. If the carbon number is too large, the light resistance may decrease, and if the carbon number is 3 or less, the solubility becomes low, which is not practical. R ² is an alkyl group having 4 to 7 carbon atoms which may be branched, and a plurality of R ² may be the same or different. If the carbon number of R ² is 3 or less or 8 or more, the extinction coefficient deviates from the required value and the object of the present invention cannot be achieved.

As the compound of the general formula (1), those produced by various methods may be used. Generally, for example, the compound of the general formula (2) is used.

[0011]

[Chemical 4]

(Wherein OR ¹ and R ¹ have the same meanings as described above) and a compound represented by the general formula (3) (R ² O) ₂ P (O) OH (3) , R ² have the same meanings as described above). The conditions for this reaction are:
Although it may be appropriately determined depending on the situation, specifically, the compound of the general formula (3) is 1 to 50 times molar equivalent, preferably 5 to 30 times molar equivalent of the compound of the general formula (2), if necessary. For example, in the presence of a solvent, 40 to 250 ° C, preferably 80 to 250 ° C.
It is obtained by reacting at 200 ° C. for 1 to 20 hours, preferably 3 to 15 hours. As the solvent used as necessary,
Examples thereof include pyridine, picoline, dimethyl sulfoxide, dimethylformamide and the like.

The compound of the general formula (2) has the formula (4)

[0014]

[Chemical 5]

(Wherein R ¹ has the same meaning as described above)
The compound can be synthesized by a conventional method. [For example, Inorg. Chem. , Vol. 4,128 (1
965)].

A write-once disc corresponding to a CD or a CD-ROM is usually composed of a transparent substrate / recording film / reflection film. As the transparent substrate, polycarbonate carbonate resin,
Polymethylmethacrylate resin, glass, polyolefin resin and the like are used, and polycarbonate resin is particularly preferably used. As the reflective film, gold, silver, platinum, aluminum or the like can be used, and gold is particularly preferably used. The film forming method of the recording film includes spin coating,
It is carried out by a vacuum vapor deposition method or a roll coating method, preferably a spin coating method.

[0017]

The present invention will be described in detail with reference to the following examples. Example 1 [in the general formula (1), R ¹ = n-C ₅ H ₁₁ ,
R ² = Compound of n-C ₄ H ₉ ] Silicon phthalocyanine (in the general formula (2), R ¹ =
A mixture of 2 g of an n-C ₅ H ₁₁ compound) and 11 g of dibutyl phosphate was stirred at 140 ° C. for 12 hours. After cooling, chloroform was added and filtered, and the filtrate was washed with water. After drying over sodium sulfate, concentrating and chloroform-
Purification was performed by silica gel chromatography using a mixed solvent of methanol, and recrystallization was performed using a mixed solvent of hexane-acetone. The yield was 1.2 g. The product was soluble in chloroform and ethanol. The maximum absorption wavelength λmax is 695 nm (CHC
It was l _3). The NMR spectrum of the obtained compound is shown in FIG. 1, and the absorption spectrum of the thin film is shown in FIG. The physical properties are shown in Table 1.

Example 2 [In the general formula (1), R ¹ = n
As -C ₄ H _9, the compound of _{^{R 2 = n-C 4 H}} 9] phthalocyanine, except that in the general formula (2) with a compound of _{^{R 1 = n-C 4 H}} 9, in the same manner as in Example 1 I went. The yield was 1.3g. The product was soluble in chloroform, ethanol and the like.
The maximum absorption wavelength λmax was 696 nm (CHCl ₃ ). The NMR spectrum of the obtained compound is shown in FIG. 3, and the absorption spectrum of the thin film is shown in FIG. In addition, the physical properties are first
Shown in the table.

Comparative Examples 1 to 3 Using compounds corresponding to R ¹ and R ² shown in Table ¹ ,
An experiment was conducted in the same manner as in Example 1. The physical properties are shown in Table 1. In addition, all the compounds of Examples 1 and 2 and Comparative Examples 1 to 3 had light resistance having no practical problem even when irradiated with light of 50,000 lux for 30 days.

[0020]

[Table 1]

[0021]

[Table 2]

[0022]

According to the present invention, CD-compatible or CD-
It is possible to obtain a dye satisfying the physical properties, solubility, extinction coefficient, optical reflectance, and light resistance required for the dye that is the recording film of the write-once optical disc for ROM, and that can be produced from an inexpensive raw material. A write-once optical disc using the same as a recording film can be obtained.

[Brief description of drawings]

1 is an NMR spectrum of the compound obtained in Example 1. FIG.

2 is an absorption spectrum of the thin film obtained in Example 1. FIG.

3 is an NMR spectrum of the compound obtained in Example 2. FIG.

FIG. 4 is an absorption spectrum of the thin film obtained in Example 2.

Claims (2)

[Claims] 1. A compound represented by the general formula (1): (In the formula, OR ¹ is bonded to the 4-position or 4′-position of each benzene nucleus, R ¹ is an alkyl group having 4 or more carbon atoms, and a plurality of R ¹ may be the same or different. . R
² is an alkyl group having 4 to 7 carbon atoms, and a plurality of R ² may be the same or different, and is compatible with a compact disk having a recording film or a compact disk-ROM compatible. Write-once optical disc. 2. A compound represented by the general formula (1): A dye for a recording film, which is composed of a compound represented by the formula (wherein OR ¹ , R ¹ and R ² have the same meanings as described above) and is used for a write-once optical disc compatible with a compact disc or a compact disc-ROM.