DE102006057130A1 - Recording layer for high density optical recording medium, e.g. optical disc, includes organic dye - Google Patents

Abstract

A recording layer comprises an organic dye. A recording layer comprises a dye of formula (I). n : 0 or 1; X : O or C(CN) 2; A : optionally substituted cyclic alkyl group; and R 1>-R 10>H, halo, 1-18(1-18C) alkyl, 1-8(1-18C) alkoxy, 1-18(1-18C) carboxyl, optionally substituted amino, 1-8(1-18C) alkyl ester, 1-18(1-18C) carboxyl, benzene including amino or carboxyl, nitro, adamantyl carbonyl, adamantyl, alkenyl, alkynyl, amino, azo, aryl, aryloxy, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy, aryloxycarbonyloxy, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkoxycarbonyl group, carbamoyl, cyanate, cyano, formyl, formyloxy, heterocyclic, isothiocyanate, isocyano, isocyanate, nitroso, perfluoroalkyl, perfluoroalkoxy, sulfinyl, sulfonyl, silyl, or thiocyanate. Independent claims are included for: (1) a high-density optical recording medium comprising a first substrate and a cover layer, and a recording layer between the first substrate and the cover layer; and (2) a method for synthesizing the dye (I). The first substrate is 0.5-1.3 mm thick, and the cover layer is 0.01-0.7 mm thick. The first substrate comprises a land-and-groove surface on its side. A reflective layer is between the cover layer and the first substrate. A protective layer is disposed on the recording layer or the reflective layer. The recording layer is formed by spin coating, roller press, inkjet printing, or dipping. Adhering the cover layer to the reflective layer is carried out by spin coating, screen printing, or thermal glue. [Image].

Description

CROSS REFERENCE TO RELATED REGISTRATION

This application claims priority to the application in Taiwan No. 94139057, filed on Nov. 8, 2005. This application is an exemption from the patent application DE 10 2006 000 931.2 filed on January 5, 2006.

BACKGROUND THE INVENTION

Field of the invention

The The present invention relates to dyes, their preparation and use for a recording layer for producing a high-density optical Recording medium.

description the associated technology

In recent years, the development of optical recording media, the lasers have been considerable. An example of the optical Recording medium, such as an optical disc, is generally configured such that a focused laser beam of about 1 micron on a thin recording layer is blasted, which is applied to a disc-shaped substrate is to execute the recording of information. The recording is in a way that implements absorption of the energy of the Laser beam, the irradiated portion of the recording layer of a thermal deformation, such as decomposition, evaporation or melting. Reproduction of the recorded information by reading the difference of the reflectance between the Section, which is a deformation caused by the laser beam and the section without this deformation.

Accordingly An optical recording medium needs the energy of the laser beam absorb effectively, and must also absorb a predetermined amount Amount of light of a laser beam using one used for recording specific wavelength has, and have a high reflectivity for a laser beam, the one for the reproducing used has specific wavelength to reproduce to execute information exactly to be able to.

however is the storage capacity the optical recording medium using the laser source, restricted due to optical diffraction. Currently some are Principles and methods of increase the storage density of the optical information storage media is discussed, including such as shifting the wavelength of the laser source, for example, from a red laser to a blue laser, or increase the objective numerical aperture ("NA") of the optical lens Close the procedure Improvement of the coding method of the digital signal on, or suggest a disk storage method by using extra fine resolution the optical field structure, or a technology, the storage capacity of the information storage medium (e.g., a compact disc) by using multiple ones to increase lying recording layers, i. the recording layers The information storage media are in a three-dimensional space structure introduced with several layers to increase the storage capacity. All methods described above can be applied to the storage capacity of the optical recording medium effectively increase.

In the method of shifting to a shorter wavelength laser source in 2002, a new generation of high-density disc storage specification (Blue-ray Disc) from companies such as Hitachi, LG, National, Pioneer, Philips, Samsung, Sharp, Sony and Thomson Multimedia released. A one-sided Blu-ray Disc can have up to 27GB of memory using a 405 nm blue laser source and a capping layer structure of 0.1 mm for the optical transmission. Thus, the optical recording medium that is a short wavelength laser source for reading and store operations used, the main branch in the development of high-density optical Become recording media.

Around to remedy the disadvantages of the prior art presented The present invention addresses the problem of novel compounds for the preparation of optical recording media.

These Task is solved by the teaching of the independent claims. Further advantageous embodiments will become apparent from the description, the examples and the figures.

SUMMARY THE INVENTION

The The present invention provides compounds, their preparation and Use for a recording layer for the recording of high density information. These Compounds herein also referred to as dyes are for the manufacture an optical recording medium comprising a short wavelength laser source with one wavelength used by not more than 530 nm.

deren Herstellung und Verwendung für eine Aufzeichnungsschicht zur Herstellung eines hochdichten optischen Aufzeichnungsmediums, wobei die Reste X sowie R¹ bis R¹⁰ und n die unten beschriebene Bedeutung haben.Accordingly, the present invention relates to compounds of general formula (I),

their preparation and use for a recording layer for producing a high-density optical recording medium, wherein the radicals X and R ¹ to R ¹⁰ and n have the meaning described below.

According to one Aspect of the present invention comprises the above-mentioned dye an absorption at wavelengths in a range of 300 to 600 nm, and is excellent, which the light fastness and thermal stability concerns.

wobei n eine ganze Zahl von 0 oder 1 ist, X ein Sauerstoffatom oder C(CN)₂ darstellt, A eine substituierte oder unsubstituierte zyklische Alkylgruppe darstellt und R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉, R₁₀ ein Wasserstoffatom, ein Halogenatom, eine Alkylgruppe mit einer Kohlenstoffanzahl 1-18 (C_1-18), eine Alkoxygruppe mit einer Kohlenstoffanzahl 1-8 (C_1-18), eine Carboxylgruppe mit einer Kohlenstoffanzahl 1-18 (C_1-18), eine Aminogruppe, eine substituierte Aminogruppe, eine Alkylestergruppe mit einer Kohlenstoffanzahl 1-8 (C_1-18), eine Carboxylgruppe mit einer Kohlenstoffanzahl 1-18 (C_1-18), Benzol einschließend eine Aminogruppe oder Carboxylgruppe, Nitrogruppe, Adamantylcarbonylgruppe, Adamantylgruppe, Alkenylgruppe, Alkynylgruppe, Aminogruppe, Azogruppe, Arylgruppe, Aryloxygruppe, Arylcarbonylgruppe, Aryloxycarbonylgruppe, Arylcarbonyloxygruppe, Aryloxycarbonyloxygruppe, Alkylcarbonylgruppe, Alkylcarbonyloxygruppe, Alkoxycarbonyloxygruppe, Alkoxycarbonylgruppe, Carbamoylgruppe, Cyanatgruppe, Cyanogruppe, Formylgruppe, Formyloxygruppe, heterozyklische Gruppe, Isothiocyanatgruppe, Isocyanogruppe, Isocyanatgruppe, Nitrosogruppe, Perfluoralkylgruppe, Perfluoralkoxygruppe, Sulfinylgruppe, Sulfonylgruppe, Silylgruppe oder Thiocyanatgruppe dar.The above-mentioned dye of the present invention has the following general chemical structural formula:

wherein n is an integer of 0 or 1, X represents an oxygen atom or C (CN) ₂ , A represents a substituted or unsubstituted cyclic alkyl group, and R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R _{10 is} a hydrogen atom, a halogen atom, an alkyl group having a carbon number of 1-18 (C _1-18 ), an alkoxy group having a carbon number of 1-8 (C _1-18 ), a carboxyl group having a Carbon number 1-18 (C _1-18 ), an amino group, a substituted amino group, an alkylester group having a carbon number of 1-8 (C _1-18 ), a carboxyl group having a carbon number of 1-18 (C _1-18 ), including benzene an amino group or carboxyl group, nitro group, adamantylcarbonyl group, adamantyl group, alkenyl group, alkynyl group, amino group, azo group, aryl group, aryloxy group, arylcarbonyl group, aryloxycarbonyl group, arylcarbonyloxy group, aryloxycarbonyloxy group, alkylcarbonyl group, alkylcarbonyloxy group, alkoxycarbonyloxy group, alkoxycarbonylg group, carbamoyl group, cyanato group, cyano group, formyl group, formyloxy group, heterocyclic group, isothiocyanato group, isocyanato group, isocyanato group, nitroso group, perfluoroalkyl group, perfluoroalkoxy group, sulfinyl group, sulfonyl group, silyl group or thiocyanate group.

Of the Dye of the present invention can be used, for example, for a recording layer an optical recording medium. As the dye of the present invention absorption at a wavelength in the range from 300 nm to 600 nm, it is possible to use a high-density optical recording medium producing a short wavelength laser source having a wavelength less than 530 nm, preferably a laser source with a wavelength of 405 nm, for the recording of high-density information and reproduction / reproduction high-density information records.

SHORT DESCRIPTION THE DRAWINGS

The accompanying drawings are included to further understand the art Invention and are incorporated in this specification and represent a part of it. The drawings illustrate embodiments of the invention and, together with the description, serve to explain the principles of the invention.

1 Fig. 12 illustrates a UV / visible light / IR absorption spectrum of the dye derivative (1) of the present invention.

2 Fig. 10 illustrates a UV / visible light / IR absorption spectrum of the dye derivative (2) of the present invention.

3 Fig. 14 illustrates a reflection spectrum for the disc comprising an HD-DVD-R recording layer of the dye derivative (1) of the present invention.

4 FIG. 11 illustrates a cross-sectional view of a high-density optical recording medium according to an embodiment of the present invention. FIG.

DESCRIPTION THE INVENTION

It It should be understood that both the preceding general Description as well as the following detailed description by way of example and serve to further explain the invention as claimed provide.

wobei n eine ganze Zahl von 0 oder 1 ist, X ein Sauerstoffatom oder C(CN)₂ darstellt, A eine substituierte oder unsubstituierte zyklische Alkylgruppe darstellt und R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉, R₁₀ ein Wasserstoffatom, ein Halogenatom, eine Alkylgruppe mit der Kohlenstoffanzahl 1-18 (C_1-18), eine Alkoxygruppe mit einer Kohlenstoffanzahl 1-8 (C_1-18), eine Carboxylgruppe mit einer Kohlenstoffanzahl 1-18 (C_1-18), eine Aminogruppe, eine substituierte Aminogruppe, eine Alkylestergruppe mit einer Kohlenstoffanzahl 1-8 (C_1-18), eine Carboxylgruppe mit einer Kohlenstoffanzahl 1-18 (C_1-18), Benzol einschließend eine Aminogruppe oder Carboxylgruppe, Nitrogruppe, Adamantylcarbonylgruppe, Adamantylgruppe, Alkenylgruppe, Alkynylgruppe, Aminogruppe, Azogruppe, Arylgruppe, Aryloxygruppe, Arylcarbonylgruppe, Aryloxycarbonylgruppe, Arylcarbonyloxygruppe, Aryloxycarbonyloxygruppe, Alkylcarbonylgruppe, Alkylcarbonyloxygruppe, Alkoxycarbonyloxygruppe, Alkoxycarbonylgruppe, Carbamoylgruppe, Cyanatgruppe, Cyanogruppe, Formylgruppe, Formyloxygruppe, heterozyklische Gruppe, Isothiocyanatgruppe, Isocyanogruppe, Isocyanatgruppe, Nitrosogruppe, Perfluoralkylgruppe, Perfluoralkoxygruppe, Sulfinylgruppe, Sulfonylgruppe, Silylgruppe oder Thiocyanatgruppe dar.The present invention provides a dye, its preparation and use for a recording layer for producing a high density optical recording medium using a short wavelength laser source having a wavelength of less than 530 nm for recording high density information and reproducing / reproducing the high density information records. The dye has the following general chemical structural formula:

wherein n is an integer of 0 or 1, X represents an oxygen atom or C (CN) ₂ , A represents a substituted or unsubstituted cyclic alkyl group, and R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R _{10 is} a hydrogen atom, a halogen atom, an alkyl group having the carbon number 1-18 (C _1-18 ), an alkoxy group having a carbon number 1-8 (C _1-18 ), a carboxyl group having a Carbon number 1-18 (C _1-18 ), an amino group, a substituted amino group, an alkylester group having a carbon number of 1-8 (C _1-18 ), a carboxyl group having a carbon number of 1-18 (C _1-18 ), including benzene an amino group or carboxyl group, nitro group, adamantylcarbonyl group, adamantyl group, alkenyl group, alkynyl group, amino group, azo group, aryl group, aryloxy group, arylcarbonyl group, aryloxycarbonyl group, arylcarbonyloxy group, aryloxycarbonyloxy group, alkylcarbonyl group, alkylcarbonyloxy group, alkoxycarbonyloxy group, alkoxycarbonylgru ppe, carbamoyl group, cyanato group, cyano group, formyl group, formyloxy group, heterocyclic group, isothiocyanato group, isocyanato group, isocyanato group, nitroso group, perfluoroalkyl group, perfluoroalkoxy group, sulfinyl group, sulfonyl group, silyl group or thiocyanato group.

The dye (I) of the present invention exhibits absorption in a wavelength range of 300 to 600 nm and is excellent in light fastness and thermal stability. For this reason, it is possible to produce a high-density optical medium by using the recording layer containing the dye of the present invention, so that a short-wavelength laser having a wavelength of less than 530 nm, preferably a blue laser having a wavelength of 405 nm for recording high-density information on the recording layer and for reproduction / re-recording The same can be used.

wobei n eine ganze Zahl von 0 oder 1 in Ausgangsmaterialien (a) und (b) ist, R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈, R₉, R₁₀ stellen unanhängig voneinander ein Wasserstoffatom, ein Halogenatom, eine Alkylgruppe mit einer Kohlenstoffanzahl 1-18 (C_1-18), eine Alkoxygruppe mit einer Kohlenstoffanzahl 1-8 (C_1-18), eine Carboxylgruppe mit einer Kohlenstoffanzahl 1-18 (C_1-18), eine Aminogruppe, eine substituierte Aminogruppe, eine Alkylestergruppe mit einer Kohlenstoffanzahl 1-8 (C_1-18), eine Carboxylgruppe mit einer Kohlenstoffanzahl 1-18 (C_1-18), Benzol, das Aminogruppe oder Carboxylgruppe, Nitrogruppe, Adamantylcarbonylgruppe, Adamantylgruppe, Alkenylgruppe, Alkynylgruppe, Aminogruppe, Azogruppe, Arylgruppe, Aryloxygruppe, Arylcarbonylgruppe, Aryloxycarbonylgruppe, Arylcarbonyloxygruppe, Aryloxycarbonyloxygruppe, Alkylcarbonylgruppe, Alkylcarbonyloxygruppe, Alkoxycarbonyloxygruppe, Alkoxycarbonylgruppe, Carbamoylgruppe, Cyanatgruppe, Cyanogruppe, Formylgruppe, Formyloxygruppe, heterozyklische Gruppe, Isothiocyanatgruppe, Isocyanogruppe, Isocyanatgruppe, Nitrosogruppe, Perfluoralkylgruppe, Perfluoralkoxygruppe, Sulfinylgruppe, Sulfonylgruppe, Silylgruppe oder Thiocyanatgruppe einschließt, dar.

wobei in Ausgangsmaterial (c) A substituierte oder unsubstituierte zyklische Alkylgruppe darstellt, X stellt ein Sauerstoffatom oder C(CN)₂ dar.According to one embodiment of the present invention, the dye (I) of the present invention can be synthesized by using the following starting materials:

wherein n is an integer of 0 or 1 in starting materials (a) and (b), R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ unanhängig represent a hydrogen atom, a halogen atom, an alkyl group having a carbon number 1-18 (C _1-18), an alkoxy group having a carbon number of 1-8 (C _1-18), a carboxyl group having a carbon number 1-18 (C _{1- 18} ), an amino group, a substituted amino group, an alkylester group having a carbon number of 1-8 (C _1-18 ), a carboxyl group having a carbon number of 1-18 (C _1-18 ), benzene, amino group or carboxyl group, nitro group, adamantylcarbonyl group , Adamantyl, alkenyl, alkynyl, amino, azo, aryl, aryloxy, arylcarbonyl, aryloxycarbonyl, arylcarbonyloxy, aryloxycarbonyloxy, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkoxycarbonyl, carbamoyl, cyanato, cyano, formyl, formyl oxy group, heterocyclic group, isothiocyanato group, isocyanato group, isocyanato group, nitroso group, perfluoroalkyl group, perfluoroalkoxy group, sulfinyl group, sulfonyl group, silyl group or thiocyanate group.

wherein in starting material (c) A represents a substituted or unsubstituted cyclic alkyl group, X represents an oxygen atom or C (CN) ₂ .

Of the Dye (I) of the present invention can be prepared by the following chemical Reaction be synthesized.

It follow some of the specific derivatives of the dye (I) of the present invention Invention. However, the scope of the present invention is not limited to the examples listed below.

below becomes the chemical synthesis of the specific dye derivatives (1), (2), (3) and (4) of the dye (I) of the present invention.

SYNTHESIS EXAMPLE 1

12:02 N, N-diethylaminobenzaldehyde and 0.01 mol of starting material (c) (X is oxygen atom) were dissolved in 20 mol of methanol and the resulting solution Heated under reflux for 8 hours. After this When the reaction was complete, the product was filtered and dried to light orange, to obtain solidified crystals. It was found that the yield approximately 80%. The chemical structure of this derivative is shown below.

A Sample of the above dye derivative (1) was dissolved in ethanol and the resulting solution was used to measure the absorbance in a spectrophotometer to eat.

The above dye derivative solution showed a maximum absorbance at 471 nm.

SYNTHESIS EXAMPLE 2

12:02 moles of N, N-dimethylaminobenzaldehyde and 0.01 moles of crude material (c) (X is oxygen atom) were dissolved in 20 mol of methanol, and the resulting solution was refluxed for 8 hours. After the reaction was complete, the product was filtered and dried to bright orange solidified crystals to obtain. It was found that the yield was about 80% is. The chemical structure of this derivative is shown below.

A Sample of the above dye derivative (2) was dissolved in ethanol and the resulting solution was used to measure the absorbance in a spectrophotometer to eat.

The above dye derivative solution showed a maximum absorbance at 466 nm.

SYNTHESIS EXAMPLE 3

12:02 moles of N, N-dibutylaminobenzaldehyde and 0.01 moles of crude material (c) (X is oxygen atom) were dissolved in 20 mol of methanol, and the resulting solution was refluxed for 8 hours. After the reaction was complete, the product was filtered and dried to bright orange solidified crystals to obtain. It was found that the yield was about 80% is. The chemical structure of this derivative is shown below.

A Sample of the above dye derivative (3) was dissolved in ethanol and the resulting solution was used to measure the absorbance in a spectrophotometer to eat.

The above dye derivative solution showed a maximum absorbance at 466 nm.

SYNTHESIS EXAMPLE 4

12:02 mol of N, N-diheptylaminobenzaldehyde and 0.01 mol of crude material (c) were dissolved in 20 mol of methanol, and the resulting solution was refluxed for 8 hours. After the reaction was complete, the product was filtered and dried to bright orange solidified crystals to obtain. It was found that the yield was about 80% is. The chemical structure of this derivative is shown below.

A Sample of the above dye derivative was dissolved in ethanol and the resulting solution was used to measure the absorbance in a spectrophotometer to eat.

The above dye derivative solution showed a maximum absorbance at 464 nm.

1 Fig. 10 illustrates a UV / visible light / IR absorption spectrum of the dye derivative (1) of the present invention.

2 Fig. 10 illustrates a UV / visible light / IR absorption spectrum of the dye derivative (1) of the present invention.

3 Fig. 12 illustrates a reflection spectrum for the HD-DVD-R recording layer containing disc of the dye derivative (1) of the present invention.

Hereinafter, a structure of a high-density blue-ray optical recording medium will be described with reference to FIG 4 described as follows. With reference to 4 For example, the high density optical recording medium comprises a first substrate 400 , a topcoat 408 and at least one recording layer 402 containing at least one of the derivatives of the dye (I) of the present invention described above disposed between the first substrate 400 and the topcoat 408 , Furthermore, a reflection layer 406 on the recording layer 402 can be provided and, if necessary, a Grundan coating layer on the first substrate 400 be provided, a protective layer 404 can on the recording layer 402 or the reflection layer 406 and a surface protective layer may be provided on the first substrate 400 on the recording layer 402 be provided opposite layer.

According to one aspect of the present invention, the first substrate is 400 and the topcoat 408 preferably transparent to the laser beam. The material of the first substrate 400 and the topcoat 408 For example, but not limited to, may include glass or plastic materials. From various aspects, the plastic material is preferably used. The plastic material may include, but is not limited to, polycarbonate (PC), polymethyl methacrylate (PMMA), polymer resins, glass, acrylic resin, methacrylic resin, vinyl acetate resin, vinyl chloride resin, nitrocellulose, polyethylene resin, polypropylene resin, polycarbonate resin, polyimide resin, epoxy resin, polysulfone resin, and metallocene-based cyclic olefin copolymer (mCOC). Of the above-mentioned plastic materials, an injection molded polycarbonate resin substrate may be of particular interest from the viewpoint of high productivity, low cost and moisture resistance. The thickness of the first substrate 400 may be between 0.5 to 1.3 mm, more preferably about 0.6 mm. The first substrate 400 includes, for example, Lands, or prefabricated, spiral-shaped (pre-curved) pits or grooves with a track pitch of less than 0.4 μm. The Lands, or prefabricated, spiral-shaped (pre-curved) pits or grooves in the first substrate 400 are used to provide a signal surface for finding the track of the scanning head of the laser.

According to one aspect of the present invention, the recording layer 402 of the present invention containing the dye (I) in a thickness in a range of about 10 Å to 500 nm, preferably in a range of about 5 nm to 200 nm. The recording layer 402 The present invention can be applied by using well-known thin film deposition methods such as a spin coating method, a roll pressing method, a vacuum vapor deposition method, a vapor deposition method, a doctor blade coating method, a casting method, an ink printing method or a dipping method. However, the spin coating method is preferred from the viewpoint of productivity and cost. A 1.5% by weight solution of the dye (I) of the present invention in 2,2,3,3-tetrafluoropropanol can be prepared and used to spin coat the thin film recording layer 402 over the first substrate 400 applied. It should also be noted that other solvents such as alcohol, ketone, ether, chloroform or dichloromethane can be used to prepare the dye solution to form the thin film recording layer 402 to create. Preferred examples of alcohol include 2,2,3,3-tetrafluoropropanol, methanol, ethanol and isopropanol. Preferred examples of ketone include acetone and dimethyl ethyl ketone. Preferred examples of ethers include ethyl ether and tetrahydrofuran.

According to one aspect of the present invention, the reflection layer 406 for example, but not limited to, metals such as gold, silver, copper, aluminum or platinum, titanium and alloys thereof, or equivalents thereof having a high reflectance in the laser wavelength range used. The thickness of the reflection layer 406 may be about 1 nm to 300 nm. The reflection layer 406 can on the recording layer 402 be applied using vacuum coating.

Finally, the topcoat can 408 above the reflection layer 406 be adhered to complete the production of the high-density optical blue-ray recording medium. The cover layer 408 can over the reflection layer 406 be applied by spin coating, screen printing, thermal bonding or roll pressing.

According to one Aspect of the present invention may be the surface protective layer on the high-gloss mirror side of the first substrate, for example, but not limited to from a UV-cured Acrylic resin or a hard coating agent of the silicone type. The protective layer is preferably with an antistatic property equipped to prevent dust or the like from sticking.

The recording layer 402 The optical recording medium of the present invention may be on one side of the first substrate 400 be upset. According to one aspect of the present invention, a plurality of recording layers may be used to make a structure of the recording medium having a plurality of superimposed layers, with the aim of further increasing the storage capacity of the optical recording medium.

The Recording on an optical recording medium thus obtained can be executed be made by a laser beam with a wavelength of not more than 530 nm, for example using a blue laser with one wavelength of 405 nm, is irradiated to the recording layer. On the Section that is illuminated with the laser beam, can be a thermal Deformation of the recording layer, such as decomposition, evaporation or melting due to absorption of the laser energy. Reproduction of the recorded information can be carried out by the difference of the reflectance between the section, such a thermal deformation caused by a laser beam and the section that does not undergo such thermal deformation is read.

The Recording and reproduction properties of the above optical Recording medium was calculated by placing a PULSTEC ODU-1000 instrument under the conditions that a blue laser beam with a wavelength of 405 nm, an objective lens with numerical aperture (NA) of 0.65, CLV = 6.61 m / s, reference layer (Ag) = 150 nm; Type 1: high to low, Reference (16% ~32 %); Type 2: low to high, reference (14% ~28%), and recording pattern 3T, 11T. It was found that the recording performance in one area from 7 to 12 mW and that the reading power is 0.5 mW. As can be seen from the results of the recording shown in Table 1 below. and reproduction characteristics, that the optical recording medium, which contains the recording layer containing the dye derivatives (1-4) of the present invention, constantly recording and reading powers below 10 mW and the CNR of both recording patterns 3T, 11T was consistently high, for example between 40-50 dB. Consequently can the organic dye derivatives (1-4) of the present invention described above Invention practically as an optical recording material for a recording layer for, to Example, a blue-ray HD-DVD-R will be used.

Table 1

Where n represents the real part of the refraction for the dye film, k represents the imaginary part of the dye film refraction, I _11L represents the reflectance for the mark of 11T after writing a disc, and CNR represents the carrier-to-noise ratio.

There the recording layer containing the dye (I) of the present invention Contains invention Absorption in the range of 300 to 600 nm shows, and excellent is in terms of light fastness and thermal stability, Is it possible a short wavelength laser with one wavelength of not more than 530 nm, preferably a blue laser with one wavelength of about 405 nm to record high-density information on it and the reproduced on it for high density information. Consequently allows the recording layer containing the dye (I) is the preparation a high-density optical recording medium.

a One skilled in the art will appreciate that various changes and variations are made the structure of the present invention can be made without to depart from the scope or spirit of the invention. In terms of the foregoing is intended to be the present invention on changes and variations of this invention, provided they fall within the scope of the following claims and their equivalents.

Claims (4)

A production process for a dye (I) of the general formula

wherein n is an integer of 0 or 1, X represents an oxygen atom or C (CN) ₂ , A represents a substituted or unsubstituted cyclic alkyl group, and R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R _{10 is} a hydrogen atom, a halogen atom, an alkyl group having a carbon number of 1-18 (C _1-18 ), an alkoxy group having a carbon number of 1-8 (C _1-18 ), a carboxyl group having a Carbon number 1-18 (C _1-18 ), an amino group, a substituted amino group, an alkylester group having a carbon number of 1-8 (C _1-18 ), a carboxyl group having a carbon number of 1-18 (C _1-18 ), including benzene an amino group or carboxyl group, nitro group, adamantylcarbonyl group, adamantyl group, alkenyl group, alkynyl group, amino group, azo group, aryl group, aryloxy group, arylcarbonyl group, aryloxycarbonyl group, arylcarbonyloxy group, aryloxycarbonyloxy group, alkylcarbonyl group, alkylcarbonyloxy group, alkoxycarbonyloxy group, alkoxycarbonylg represents a group, carbamoyl group, cyanato group, cyano group, formyl group, formyloxy group, heterocyclic group, isothiocyanato group, isocyanato group, isocyanato group, nitroso group, perfluoroalkyl group, perfluoroalkoxy group, sulfinyl group, sulfonyl group, silyl group or thiocyanate group, which comprises the following:

wherein a reaction temperature (T) is between -15 ° C to 150 ° C and a reaction time (t) is longer than one minute. A dye of the general formula (I),

wherein n is an integer of 0 or 1, X represents an oxygen atom or C (CN) ₂ , A represents a substituted or unsubstituted cyclic alkyl group, and R ₁ , R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R _{10 is} a hydrogen atom, a halogen atom, an alkyl group having the carbon number 1-18 (C _1-18 ), an alkoxy group having a carbon number 1-8 (C _1-18 ), a carboxyl group having a Carbon number 1-18 (C _1-18 ), an amino group, a substituted amino group, an alkylester group having a carbon number of 1-8 (C _1-18 ), a carboxyl group having a carbon number of 1-18 (C _1-18 ), including benzene an amino group or carboxyl group, nitro group, adamantylcarbonyl group, adamantyl group, alkenyl group, alkynyl group, amino group, azo group, aryl group, aryloxy group, arylcarbonyl group, aryloxycarbonyl group, arylcarbonyloxy group, aryloxy carbonyloxy, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkoxycarbonyl, carbamoyl, cyanato, cyano, formyl, formyloxy, heterocyclic, isothiocyanato, isocyanato, isocyanato, nitroso, perfluoroalkyl, perfluoroalkoxy, sulfinyl, sulfonyl, silyl, thiocyanate. Compounds according to claim 2 selected from the group of the following compounds:

Use of the dye of the formula (I) according to claim 2 or 3 for a recording layer for producing a high-density optical Recording medium.