JPH08808B2 - Naphtolactam compounds and light absorbing dyes - Google Patents

Description

TECHNICAL FIELD The present invention relates to a naphtholactam compound and a light absorbing dye.

2. Description of the Related Art Optical recording using a laser enables high-density information recording, storage, and reproduction, and thus has been particularly desired for development in recent years.

An example of optical recording is an optical disc.

In general, an optical disc is one in which a thin recording layer provided on a circular substrate is irradiated with laser light focused to about 1 μm to perform high density information recording.

Recording is generated by thermal deformation of the recording layer, such as decomposition, evaporation, and dissolution, which occurs at the location due to absorption of the laser energy applied, and reproduction of recorded information is transformed by laser light. This is done by reading the difference in reflectance between the part where the noise occurs and the part where no noise occurs.

Therefore, it is necessary for the recording medium to absorb the energy of the laser light efficiently, so it has a large absorption for the laser light of the specific wavelength used for recording, and it is used for reproduction in order to accurately reproduce the information. It is necessary that the reflectance with respect to the laser light of the specified wavelength is high.

Various types of optical recording media are known as this type of optical recording medium.

For example, JP-A-55-97033 discloses a substrate in which a single layer of a phthalocyanine dye is provided. Phthalocyanine dyes have problems such as low sensitivity, high decomposition point and difficulty in vapor deposition, and also have extremely low solubility in organic solvents and cannot be used for coating by coating. .

Further, JP-A-58-83344 and JP-A-58-224793 disclose a recording layer containing a phenalene dye and a naphthoquinone dye, respectively. However, such dyes have the advantage of being low in reflectivity, while having the advantage of being easily deposited. When the reflectance is low, the contrast relating to the reflectance between the portion recorded by the laser beam and the unrecorded portion is low, and it becomes difficult to reproduce the recorded information.

Further, JP-A-59-24692, JP-A-59-67092, and JP-A-59-71895 disclose a recording layer provided with a cyanine dye. However, while such a dye has the advantage that it can be used for coating by coating, it has the problems of light resistance and deterioration due to reproduction light.

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention The present invention provides a novel naphtholactam compound having high solubility in an organic solvent, high reflectance, and excellent light resistance and reproduction light resistance and a light absorbing dye. The object of the present invention is to provide an optical recording material containing the compound.

Means for Solving the Problems The present invention provides a light-absorbing dye for optical recording, which comprises a naphtholactam compound represented by the following general formula [I] and a substrate, and a recording layer containing the light-absorbing dye. The gist is a light absorbing dye for an optical recording material, wherein the absorbing dye is a naphtholactam compound represented by the following general formula [I].

General formula [I] (In the formula, K represents a residue of a substituted or unsubstituted aromatic amine, R represents a substituted or unsubstituted alkyl group, cycloalkyl group, aryl group or allyl group, Z ⁻ represents an anion, Ring A represents a naphthalene ring which may have a substituent.) In the general formula [I], the substituent of the alkyl group, cycloalkyl group, aryl group or allyl group represented by R is
For example, alkoxy group, alkoxyalkoxy group, alkoxyalkoxyalkoxy group, allyloxy group, aryl group, aryloxy group, cyano group, hydroxy group,
A tetrahydrofuryl group, an allogen atom, etc. are mentioned.

Examples of the substituent of the naphthalene ring represented by ring A include halogen atoms, C _{1 to} C ₁₀ alkyl groups, C _{1 to} C ₁₀ alkoxy groups, alkylamino groups, acylamino groups, amino groups, hydroxy groups and the like Examples of the substituent include a sexual substituent.

The residue of the substituted or unsubstituted aromatic amine represented by K is, for example, a residue of a heterocyclic amine containing a nitrogen atom, an oxygen atom or a sulfur atom, a tetrahydroquinoline, or a general formula (In the formula, X and Y represent a hydrogen atom, an alkyl group, an acylamino group, an alkoxy group or a halogen atom, and R ²
And R ³ represents a hydrogen atom or a C ₁ -C ₂ substituted or unsubstituted alkyl group, aryl group, allyl group or cyclohexyl group. ) And the like. And, as the substituent of the alkyl group, aryl group, allyl group or cyclohexyl group represented by R ² and R ³ , for example, an alkoxy group, an alkoxyalkoxy group, an alkoxyalkoxyalkoxy group, an allyloxy group, an aryl group, an aryloxy group , Cyano group, hydroxy group, tetrahydrofuryl group and the like.

Z ^- The anion ^{I -, Br -, Cl -} , ClO 4 -, BF 4 -, S
CN ^-, Etc. can be mentioned.

The naphtholactam compound represented by the general formula [I] has absorption in the wavelength band of 600 to 800 nm, and has a molecular absorption coefficient of 10 ⁴ to 10 ⁵ cm ^-1 .

Among the naphtholactam compounds represented by the above general formula [I], preferred dyes are those represented by the general formula [II] (Wherein X, Y, R ² and R ³ are the same as defined above,
R ¹ represents a substituted or unsubstituted alkyl group, cycloalkyl group, aryl group or allyl group, and R ⁴ and R ⁵
Is a hydrogen atom, a halogen atom, a C _{1 to} C ₁₀ alkyl group, C ₁
To C ₁₀ alkoxy group, alkylamino group, acylamino group, amino group or hydroxy group, and Z ⁻ represents an anion. The naphtholactam type compound shown by these is mentioned.

The novel naphtholactam-based compound of the present invention has, for example, the following general formula [III] according to the method described in British Patent No. 1,055,831. (Wherein R ¹ , R ¹ , R ⁵ and Z ⁻ are the same as defined above) and the following general formula [IV] (In the formula, X, Y, R ² and R ³ are the same as defined above.), And can be produced by condensing with cinnamic aldehydes.

The optical recording material using the light-absorbing dye of the present invention is basically composed of a substrate and a recording layer. Further, if necessary, an undercoat layer may be formed on the substrate and a recording layer may be formed on the recording layer. A protective layer can be provided.

The substrate may be transparent or opaque to the laser light used. As the material of the substrate material,
Examples thereof include a support for a general recording material such as glass, plastic, paper, plate-shaped or foil-shaped metal, and plastic is preferable from various points. Examples of the plastic include acrylic resin, methacrylic resin, vinyl acetate resin, vinyl chloride resin, nitrocellulose, polyethylene resin, polypropylene resin, polycarbonate resin, polyimide resin, polysulfone resin and the like.

When a naphtholactam compound is used as the light absorbing dye contained in the recording layer of the optical recording material, the film thickness is 10
It is 0Å to 5 μm, preferably 1000Å to 3 μm.

As a film forming method, a generally used thin film forming method such as a vacuum vapor deposition method, a sputtering method, a doctor blade method, a cast method, a spinner method and a dipping method can be used.

Further, a binder can be used if necessary. Polyvinyl alcohol (PV
Known resins such as A), polyvinylpyrrolidone (PVP), nitrocellulose, cellulose acetate, polyvinyl butyral, and polycarbonate are used, and the amount of the naphtholactam compound with respect to the resin is preferably 0.1 or more by weight ratio.

For film formation by the spinner method, the rotation speed is 500-5000 rpm
However, after spin coating, in some cases, a treatment such as heating or exposure to a solvent vapor may be performed.

As a coating solvent for forming a recording layer by a coating method such as a doctor blade method, a cast method, a spinner method, a dipping method, or a spinner method, a boiling point of bromoform, dibromoethane, ethyl cellosolve xylene, chlorobenzene, cyclohexanone, etc. One having a temperature of 160 ° C. is preferably used.

In order to improve the stability and light resistance of the recording material, a transition metal chelate compound (for example, acetylacetonate chelate, bisphenyldithiol, salicylaldehyde oxime, bisdithio-) is used as a singlet oxygen quencher.
(α-diketone, etc.) or a tertiary amine compound may be contained.

And, if necessary, other dyes can be used in combination. Other dyes include naphtholactam dyes of different types, triarylmethane dyes, azo dyes, cyanine dyes, squarylium dyes, indoaniline dyes, and the like.

The recording layer of the optical recording body may be provided on both sides of the substrate,
It may be provided on only one side.

Recording on the optical recording material obtained as described above is performed by irradiating a recording layer provided on both sides or one side of the substrate with a laser beam focused to about 1 μm, preferably a semiconductor laser beam. In the portion irradiated with laser light, thermal deformation of the recording layer such as decomposition, evaporation, and melting occurs due to absorption of laser energy.

The recorded information is reproduced by using a laser beam to read the difference in reflectance between a portion where thermal deformation has occurred and a portion where thermal deformation has not occurred.

The laser light used for the optical recording medium is N ₂ , He-
Examples thereof include Cd, Ar, He-Ne, ruby, semiconductor, dye laser, and the like, and the semiconductor laser is particularly preferable from the viewpoints of light weight, easy handling, compactness, and the like.

EXAMPLES The present invention will be specifically described below with reference to examples, but the examples do not limit the present invention.

Example 1 The following structural formula Compound represented by 40.2g and the following structural formula 17.5 g of the compound represented by
Add to a solution consisting of 0 g, stir at 100-105 ° C for 4 hours,
After completion of the reaction, the reaction solution was cooled to room temperature, and then the reaction solution was poured into 1.5 water containing 16.0 g of sodium perchlorate and stirred at room temperature for 8 hours. The precipitated crystals were taken and dried to obtain 53.0 g of the naphtholactam compound of the present invention (black green crystal) represented by the following structural formula. Λmax in the solution of the compound (chloroform) was 800 nm.

1 g of the naphtholactam compound of the present invention represented by the above structural formula was dissolved in 50 g of dibromoethane and filtered through a 0.22 μ filter to obtain a solution. Add 2 ml of this solution to a depth of 700
Å, with a groove (group) made of 0.7μm width UV curable resin, methacrylic resin (hereinafter referred to as PMMA) substrate (120m
mφ), and was applied at a rotation speed of 1200 rpm by a spinner method, and then dried at 60 ° C. for 10 minutes. It was 700Å when it was applied to a glass plate under the same conditions and the film thickness was measured by a Taris step. The maximum absorption wavelength of the coating film was 820 nm, and the spectrum was broad in shape.

When this coating film was irradiated with a semiconductor laser beam with a central wavelength of 830 nm (output 6 mW, beam 1 μm), the width was about 1 μm
m, a very clear contoured hole (pit) having a pit length of about 2 μm was formed. The carrier level / noise level (C / N) ratio was 52DB. The light resistance and the resistance to reproduction light were also good.

Example 2 According to the method described in Example 1, the following structural formula The naphtholactam compound of the present invention represented by (λmax
(Chloroform) 795 nm) was produced.

The naphtholactam compound 1g of the present invention represented by the above structural formula and nitrocellulose 1.5g (manufactured by Daicel Chemical Industries, Ltd., RS-20, trade name) are dissolved in 50g of ethyl cellosolve, and passed through a 0.22μ filter, A solution was obtained.

3 ml of this solution was dropped onto a polycarbonate resin substrate (120 mmφ) with a groove (group) having a depth of 650 Å and a width of 0.7 μm, applied at a rotation speed of 1500 rpm, and then dried at 60 ° C. for 10 minutes. To measure the film thickness, a glass plate was applied in the same manner and the film thickness was 700Å when measured by a Taris step. The maximum absorption wavelength of the coating film was 810 nm, and the peak was broad.

When this coating film was irradiated with a semiconductor laser beam with a central wavelength of 830 nm (output 6 mW, beam diameter 1 μm), the width was about 1 μm
m, a very clear contoured hole (pit) having a pit length of about 2 μm was formed. The C / N ratio was 5 / dB. The light resistance and the resistance to reproduction light were also good.

Example 3 According to the method described in Example 1, the following structural formula The naphtholactam compound of the present invention represented by (λmax
(Chloroform) 800 nm) was produced.

1 g of the naphtholactam compound represented by the above structural formula was dissolved in ethyl cellosolve and passed through a 0.22 μ filter to obtain a solution. 2 ml of this solution is 700Å in depth and 0.7 in width.
Polycarbonate resin substrate with a groove (group) of μ (13
0 nmφ), and apply at a rotation speed of 800 rpm, then 60
It was dried at 0 ° C for 20 minutes. The thickness of the film measured by a Talystep applied to a glass plate under the same conditions was 650Å. The maximum absorption wavelength of the coating film was 820 nm, and the peak was broad.

When this coating film was irradiated with a semiconductor laser beam having a central wavelength of 830 nm (output: 6 mW, beam diameter: 1 μm), a very clear contoured hole (pit) having a width of about 1 μm and a pit length of about 2 μm was formed. The C / N ratio was 52 dB. The light resistance and the resistance to reproduction light were also good.

Examples 4 to 87 According to Example 1, a naphtholactam compound of the present invention represented by the following general formula [V] shown in Table 1 was produced, and the compound was UV-cured under substantially the same conditions as in Example 1. It was applied on a PMMA resin substrate with a groove (group) made of resin.

Table 1 shows the maximum absorption wavelengths of these light-absorbing substances of the present invention in a chloroform solvent.

When the obtained coating film was irradiated with a semiconductor laser beam having a central wavelength of 830 nm, a hole with a very clear outline (bit)
Was formed, the reflectance was high, the sensitivity was high, and the C / N ratio was excellent. Further, the light resistance and the resistance to reproducing light were also good.

Effect Since the naphtholactam compound of the present invention represented by the general formula [I] has a high solubility in an organic solvent, it can be coated by coating when producing an optical recording material containing the compound for recording. . Further, since the compound has a high reflectance, it is possible to obtain an optical recording material having a good contrast. The compound is also excellent in light resistance and resistance to reproduction light.

Continuation of front page (51) Int.Cl. ⁶ Identification number Office reference number FI Technical display location C07D 409/06 209 413/06 209 417/06 209 C09B 57/06 G11B 7/24 A 7215-5D

Claims (4)

[Claims] 1. A general formula [I] (In the formula, K represents a residue of a substituted or unsubstituted aromatic amine, R represents a substituted or unsubstituted alkyl group, cycloalkyl group, aryl group or allyl group, Z ⁻ represents an anion, Ring A represents a naphthalene ring which may have a substituent). 2. The naphtholactam-based compound according to claim 1, wherein the naphtholactam-based compound is represented by the general formula [II]. (In the formula, X and Y represent a hydrogen atom, an alkyl group, an acylamino group, an alkoxy group or a halogen atom, and R ¹
Is a substituted or unsubstituted alkyl group, cycloalkyl group,
Represents an aryl group or an allyl group, R ² and R ³ represent a hydrogen atom or a C _{1 to} C ₂₀ substituted or unsubstituted alkyl group, an aryl group, an allyl group or a cycloalkyl group, and R ⁴ and R ⁵ represent hydrogen. atom, halogen atom, C ₁ -C
_{10 represents} an alkyl group, a C _{1 to} C ₁₀ alkoxy group, an alkylamino group, an acylamino group, an amino group or a hydroxy group, and Z ⁻ represents an anion. ) The naphtholactam type compound shown by these. 3. A light absorbing dye for an optical recording material comprising a substrate and a recording layer containing the light absorbing dye, wherein the light absorbing dye is a naphtholactam compound represented by the following general formula [I]. Characteristic light absorbing dye. (In the formula, K represents a residue of a substituted or unsubstituted aromatic amine, R represents a substituted or unsubstituted alkyl group, cycloalkyl group, aryl group or allyl group, Z ⁻ represents an anion, The ring A is a naphthalene ring which may have a substituent.). 4. The light-absorbing dye according to claim 3, wherein the naphtholactam compound is represented by the general formula [II]. (In the formula, X and Y represent a hydrogen atom, an alkyl group, an acylamino group, an alkoxy group or a halogen atom, and R ¹
Is a substituted or unsubstituted alkyl group, cycloalkyl group,
Represents an aryl group or an allyl group, R ² and R ³ represent a hydrogen atom or a C _{1 to} C ₂₀ substituted or unsubstituted alkyl group, an aryl group, an allyl group or a cycloalkyl group, and R ⁴ and R ⁵ represent hydrogen. atom, halogen atom, C ₁ -C
_{10 represents} an alkyl group, a C _{1 to} C ₁₀ alkoxy group, an alkylamino group, an acylamino group, an amino group or a hydroxy group, and Z ⁻ represents an anion. ) A light absorbing dye which is a naphtholactam compound.