TW513721B - Optical recording material - Google Patents

Abstract

The invention relates to an optical recording material characterized in consisting of a compound expressed by general formula (I). In formula, A independently represents a benzene ring or naphthalene ring, each of R1 and R2 is independently a 1-4C alkyl group, each of R and R' is a 1-8C alkyl group, Y is a hydrogen atom or halogen atom, Anm- is a m-valent anion, m is an integer 1 or 2, and p represents a coefficient to keep the charges neutral.

Description

513721

%% 京 [Invention Field] The present invention relates to a method that can be used for optical recording, and the optical recording medium records information = =: converted into a thermal information map ㉟, in detail, profit: 2: The optical recording and reproduction of the optical recording medium can be performed by the transport specialist, and the body: laser of the amount. [Narration of related arts] Head contact ’& recording medium: write or read magnetic ;, in particular: in other words, the information is converted into a line of == :. It is very hot, so its development is very hot, for example, its traces are high density; optically detectable depressions are formed on the layer, and the materials used in the above recording layer are based on thiazole, thiazole, and thiazole. The pantoconazole series and the formula are listed as Cyanine pigments. These pigments are various kinds of butyl pigments such as cyanine anion, phosphorous fluoride anion, etc. The ions and ions are due to the pseudoindole-type succinyl + J from -Li 丨 stone ions, in particular, used, It is very suitable for memorizing ^ ^ because of its sensation and good recording characteristics. It cannot meet the needs of the optical recording medium. Γ: Γ, reading speed, and need-a kind of tool Better track record

513721 V. Description of the invention (2) Summary of the invention Therefore, an object of the present invention is to provide an optical recording material suitable for an optical recording medium having excellent recording characteristics, and to provide an optical recording medium using the optical recording material. The inventors of the present invention reviewed it repeatedly, and found that the optical § recorded material is included in a false D bow 丨 D-based Saining pigment introduced a specific substituent group of compounds '' can achieve excellent recording characteristics Optical recording media, and up to the invention. The present invention has been completed based on the above findings, and an optical recording material is provided, which is characterized by including a compound represented by the following general formula (1): R1 R1

In the formula, A is a benzene ring or a naphthalene ring, Ri 1 is an alkyl group with a carbon edge of ~ 4, R and R 'are an alkyl group with a carbon number of 1 to 8, γ is a hydrogen atom or an atom, and AW is m. Valence anion, m is the integer i or 2, and *

It maintains a neutral coefficient and provides an optical recording medium characterized in that a thin film containing the optical recording material is formed on a substrate. The optical recording materials of the month can be obtained with excellent recording characteristics. Detailed description of the invention

513721 V. Description of the invention (3) The following is a detailed description of the optical recording medium that meets the above requirements. The optical recording material of the present invention and the compound of the general formula (I) in the present invention are the pigments on the photocatalyst layer, which are ... The milk, the creator, is an optical recording medium having excellent recording characteristics as shown in the embodiment described later, which is its characteristic. -In addition, by introducing 3-oxobutyridine, the effect of the% y solubility is sacrificed. The soil is also improved in a polar solvent. In the general formula shown above, the tooth atoms of γ are bromine and iodine. The table shows the number of carbon atoms in the heart, R2 is 1 ~ 4 ρ A, ,,,,,, propyl, propyl, isopropyl, butyl, and butyl H, such as; Γ is methyl, ethyl, and the like. The table is β, R, carbon number 1 ~ 8 & Α γ butyl, isobutylpropyl, isopropyl, butyl, second butyl group, such as-may be methyl, ethyl, a Cu-butyl, di-dibutyl, 1-butychi, 々: 丄: dipentyl, hexyl, heptyl, octyl, 2: ethylhexyl, etc. As for the anions of An „-; octyl, chloride, bromide, and anion ^ ^ 彳 If it can be a child; perchlorate anion, chloric acid; ions, anions, and other anions, such as anions, Anion: ion: hexa ion, hexadensity ion, benzoic acid anion, toluene anion, "inorganic anion ::: inorganic acid anion; octyl discic acid anion :: = anion anion, eighteen Alkyl phosphate anions, undecyl phosphate anions, 2, 2, -methylenebis (4, 1 anion, nonphenyl anion, and other organic phosphoric acid-based anion " 'etc .: tributylphenyl ) Dibasic acids such as phosphonic acid anion and naphthalenedisulfonic acid anion can be, for example, benzene disulfonic acid, or 513721 can be used as required. V. Description of the Invention (4) Digestive anion of metal complex compound. As for the above-mentioned digestive anion, it may be an anion as described in Japanese Patent Laid-Open Publication No. Sho 60-2348348. Let be the anion of the general formula ⑴ and ⑻ shown below: T is the table

Rs

Re

(B) In the formula, Rs and R4 are each a radical or a self atom, and a is each 0 to. In addition, each of R5, R6, R7, and 1 to 8 is a courtyard group, a phenyl group, or a halogenated phenyl group. It is said that the base and the milk are η. In addition, η is an integer of 1 to 3, but 11 is a compound having a sensitivity of 1 and it is preferable. Introduce and regenerate the wavetable; it is the general formula ⑴ shown above; Also, the following example is an indication of the anion-free color

$ 7 pages 513721

513721 V. Description of the invention (6) In the present invention, there is no limitation on the method for preparing the compound of the general formula (I) shown above, and it can be manufactured according to a conventionally known method and synthesized by the following path:

In the formula, X is a methylenedi group substituted with Ri and oxo, and R ', A nm_, and p are the same as the aforementioned general formula (I). The compound represented by the general formula (I) in the present invention is suitable as a recording layer for an optical recording medium. As for the formation of the recording layer, a conventionally known method can be used. Generally speaking, the method can be a low carbon number alcohol such as methanol, ethanol, a fluorene-based cellosolve, an ethyl cellosolve, a butyl cellosolve, an ether alcohol such as butyl diethylene glycol, acetone, methyl ethyl Ketones such as methyl ketone, methyl isopropyl ketone, cyclohexanone, diacetone alcohol, esters such as ethyl acetate, butyl acetate, and ethoxy ethyl acetate, and acrylates such as ethyl acrylate and butyl acrylate Fluorinated alcohols such as 2, 2, 3, 3-tetrafluoropropanol, hydrocarbons such as benzene, xylene, xylene, fluorenyl dichloride, dichloroethane, chloroform, etc. The recording layer can be easily formed by dissolving in an organic solvent and coating the obtained solution on a substrate.

513721 V. Description of the invention (7) ___ The thickness of the above-mentioned recording layer is usually within a range of 0.001 to 10 micrometers to 5 micrometers. The above recording layer: shape = 于. .〇1 law. When the present invention is included in a recording layer of an optical recording medium, the optical recording material / pre-recording material of the present invention is 50 to 100% by weight based on the recording layer. The use amount of the bucket is better. In addition to the optical recording material of the present invention, resins such as polyethylene, polystyrene, and recording layer carbonate can also be included in the lubricant according to needs. It also contains surfactants, ethylene, poly ... flame retardant zibb stabilizers, dispersants, anti-oxidants: agents, anti-electrical agents, and more. In the above recording layer, aromatic 1 = crosslinker can also be included. Wait. As the transition metal clamp compound compound, etc., as the singlet oxygen compound, etc., a known compound such as that proposed in Japanese Patent Laid-Open Publication No. ^ n can be used. Relative to the recording layer, the compound is preferably in a range of 795 to 50% by weight. ”° As for the material of the above-mentioned substrate provided with such a recording layer, any material that is substantially transparent to the writing light and the reading light may be used, and there is no particular limitation, for example, polymethyl methacrylate can be used , Polyethylene terephthalate, Polycarbonate S, Nettle month, and Glass net. In addition, the shape can be any shape such as tape, drum, ribbon, disc, etc., depending on the application. A reflective film can also be formed on the recording layer by gold, silver, aluminum, and copper equal to the above-mentioned recording layer by a vapor deposition method or a sputtering method, and a protective layer made of an acrylic resin and an ultraviolet curable resin can also be formed.

513721 Jade, description of the invention (8) The optical recording material of the present invention can be used as a dye for optical discs such as LD, CD, DVD, CD-R DVD R, etc., and is particularly suitable for use in high-speed CD-R. Hereinafter, the present invention will be described in more detail by way of Synthesis Examples, Examples, and Comparative Examples. However, the present invention is not limited in any way by the following examples. [Synthesis Example 1] (Synthesis of phosphorus hexafluoride salt of Compound No. 1) φ was placed in a 500 ml reaction flask, and "ο g (0.20 mol) of 2, 2, 3-difluorene was charged. Benzyl pseudoindole, 103 mg (0.399 mol) of 4-methylbenzylsulfonic acid 3-methoxybutyrate, reacted at 90 ° C for 1 hour, and then at 5.00. After reacting for 3 hours, 281 g of ethyl acetate was added, and the mixture was refluxed for 30 minutes, and then cooled to a temperature to crystallize the crystals. The crystals were collected by filtration, washed with ethyl acetate, and then dried at 80. Vacuum drying was performed in the downward direction to obtain 57.0 g of a white aa (yield 60.6%), which was an intermediate of the target compound. A 100-liter reaction flask was charged with 40 g of Moore. ) Of the intermediate obtained from the above Φ, 3.90 g (0.0152 mol) of N, N-diphenyl-2-chloroamidine, 23.7 g (0.300 mol) of pyridine, 4 60 g (0.0451 mole) of acetic anhydride, reacted at room temperature for 2 hours, and then reacted at 80 ° C for 1 hour. To the reaction solution was added 20.0 g of dimethylformamidine Amine, and hexafluoro (61.03 g) Phosphorus and potassium were reacted at 80 ° C for 1 hour, and then 50 g of chloroform and 50 g of water were added for oil-water separation. After washing with water twice, 30 g of methanol was added to the concentrated system. The target compound is crystallized. The obtained crystals are collected by filtration, washed with methanol, and then dried at 80.0.

513721 V. Description of the invention (9) Dry in air to obtain 1fl7 ±, 忖 iu · 7 g of green crystals (yield 88.6%), which is the target compound. The purity of the obtained crystal and the structure thereof were measured by a 1H-NMR method. The results are shown below. <Liquid Chromatography> (PEGAJIL ODS, methanol / water = 9/1, 0.7 ml / s) Number of detected peaks: 1 (retention time: 2 2 · 1 minute) &lt; H NMR (chemical shift ρριη; multiple (Proton number)> (1. 2 0 to 1 | (3. 2 0 to 3 · (4. 3 5 to 4 · (7. 4 0 to 7 · (7 · 6 1 to 7. (8 · 2 6 to 8 · 'd: 6) (1 · 9 1 to 2 · 〇9: m + s: 1 6) 5 1: s + m; 8) (4 · 2 0 to 4 · 2 7; m, · 2) 43, m; 2) (6 · 45 ~ 6.49; d; 2) "; d; 2) (7 · 4 7 ~ 7 · 5 1; t, · 2) 6 6, · t; 2 ) (7.90 to 7.94; m; 4) 2 8; d; 2) (8.3.2 to 8.36; d; 2) [Synthesis Example 2] '(Compound No. 2 of Synthesis of phosphorous hexafluoride salt) A 100 ml reaction flask was charged with 14.0 g (0.0299 mol) of the intermediate obtained in Synthesis Example 1φ above, and 3.88 g (0.0152 mol) of N, N -Diphenylpyrene gas salt, 23.7 g (0.300 mole) of pyridine, 4.60 g (0.0451 mole) of acetic anhydride, react at 80 ° C for 2 hours. 'Add 20.0 g of bis to the reaction solution Fluorenylformamide and hexafluoride with 6.10 g (0.0331 mol) Phosphorus and potassium were reacted at 80 ° C for 1 hour, and then 50 g of chloroform and 50 g of water were added for oil-water separation. After water-washing and gas-phase imitation two times, 30% was removed.

Page 12 513721 V. Description of the invention (ίο) Gram of scopolamine is added to the concentrated system to crystallize the target compound. The obtained crystal 'was collected by filtration, washed with methanol, and then dried at 80. O Drying under vacuum to obtain 9.50 g of green crystals (yield 82.2%), which is the target compound. The purity of the obtained crystal was measured by liquid chromatography, and its structure was confirmed by 1 H-NMR. The results are shown below. <Liquid Chromatography> (PEGASIL ODS 'methanol / water = 9/1, 0.7 ml / s) Measured peak number: 1 (retention time: 2 2 · 0 minutes) d-NMR (chemical shift ppm; multiplicity ; Number of protons)> (1. 2 0 to 1 (3. 3 2 to 3 (4. 2 8 to 4 (6. 5 9 to 6 (7.. 4 4 to 7 (7. 9 0 to 7 d; 6) (1.80 to 2.03; m + s; 16) s + m; 8) (4.19 to 4.26; m; 2) m; 2) (6.19 to 6. 2 2; d; 2) t; 1) (7 · 3 9 ~ 7 · 4 2; d; 2) t; 2) (7 · 5 3 ~ 7 · 6 3, · t; 2) m: 4) (8 · i 5 ～ 8 · 2 1; d + t; 4) The following σ has been shown in Table 1 'Compared with comparative compounds with similar structures ^ and 2' The above compounds No. Phosphorus salts have substantially different characteristics on the νν absorption spectrum, and the decomposition temperature (using a differential thermal analysis device) shows a value that is not less than =. The lower decomposition temperature is considered to be the main reason why an optical recording medium having excellent recording characteristics can be obtained from the optical recording material of the present invention.

Page 13 513721 V. Description of Invention (11) [Table 1]

Comparative Compound 1 PF6-Salt of Comparative Compound 2 ---------- &quot;

Comparative Compound 2

(Examples 1-1 to 1-5 and Comparative Examples 1-1-4) (Production and Evaluation of Optical Recording Media) On a polycarbonate dish-shaped substrate with a diameter of 12 cm, a titanium clamp compound (T -50 (manufactured by Soda Co., Ltd.), hydrolyzed to set it as the bottom layer (0.01 micron), and the substrate shown in Table 2 and the aromatic nitroso are coated by spin coating on the substrate. Compound (DQ — 24 Asahi Denka Kogyo Co., Ltd.'s 1: 0 · 1 (weight ratio) ethyl cellosolve solution to form a recording layer with a thickness of 100 nm. On the recording layer, borrow A gold reflective film with a thickness of OO nanometers was formed by a vapor deposition method. Each medium made in the above manner was rotated at a speed of 5.0 m / s, and a semiconductor laser (780 nanometers, a light-collecting portion) was used. The output is 8 mW and the frequency is 2.5 kHz.) The writing is performed on the bottom surface of the substrate. Secondly, a semiconductor laser (780 nm, the output of the light-collecting part is 0.4 mW) is used as the reading light. 'Detect the reflected light through the substrate and use a spectrum analyzer to

Page 14 513721 V. Description of the invention (12) Determine the C / N ratio with a width of 30 kHz. The C / N ratio is an evaluation method of recording characteristics, and the larger the value, the more excellent the recording characteristics.

[Table 2] Number pigment C / N ratio (dB) Example 1-1 PF6_salt of compound No. 1 57 1-2 PF6j of compound No. 2 53 1-3 PF6 of compound No. 3, 52 1- 4 ClO4_salt 55 of compound No. 1 1-5 C1CV salt of compound No. 2 52 Comparative example 1-1 Comparative compound 1? , Salt 42 1-2 Comparative Compound 2 PF6 • Salt 45 1-3 Comparative Compound 1 CicV Salt 41 1-4 Comparative Compound 2 C1CV Salt 43 Comparative Compounds 1 and 2 are the same as Table 1 above. Page 513721 Illustration

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Claims (1)

513721 6. Scope of patent application 1. An optical recording material characterized by comprising a compound of the general formula (I) shown below: In the formula, each of A is a benzene ring or a naphthalene ring, and ratio and R2 are each an alkyl group having 1 to 4 carbon atoms, R and R ′ are alkyl groups having 1 to 8 carbon atoms, and Y is a hydrogen atom or a halogen atom, Anm- is an anion of m valence, m is an integer of 1 or 2, and p is a coefficient that keeps the charge neutral. 2. The optical recording material according to item 1 of the scope of patent application, characterized in that in the general formula (I) shown above, A is a naphthalene ring, R2, R, R 'are methyl groups, and Y is a chlorine atom. 3. The optical recording material according to item 1 of the scope of patent application, characterized in that in the general formula (I) shown above, A is a naphthalene ring, core, R2, R, R 'are methyl groups, and Y is a hydrogen atom. 4. An optical recording medium, characterized in that a thin film is formed on a substrate, and the thin film includes optical recording materials such as those in claims 1 to 3 of the scope of patent application. Page 17