Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1992-03-18
1993-11-09
Page, Thurman K.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
540128, 540140, C07B 4730
Patent
active
052604357
DESCRIPTION:
BRIEF SUMMARY
FIELD OF ART
The present invention relates to a novel derivative of naphthalocyanine containing a perfluoroalkyl group, and particularly to a process for preparing such an industrially useful derivative of naphthalocyanine containing a perfluoroalkyl group and an optical recording medium capable of recording information using a focused beam of a semiconductor laser.
BACKGROUND TECHNOLOGY
Cyanine compounds have hitherto been known to be used as absorbents for the rays within the near infrared and infrared regions, but the cyanine compounds are generally unstable to light and heat. On the other hand, since naphthalocyanine compounds are extremely stable to light, heat and humidity and excellent in toughness, they attract attention to be used as polymer materials for preparing films or thin membranes having high performance characteristics by blending with various dyes, pigments, optical information recording media, photoelectric conversion media, electron photographic sensors and polymer materials.
However, naphthalocyanine compounds are generally scarcely soluble in organic solvents and thus difficulties are encountered in forming films thereof by ordinary film forming processing. Accordingly, there is an earnest demand for a compound having excellent properties comparable to naphthalocyanine compounds and capable of forming a film, and there is also an earnest demand for the development of a process for preparing such a compound on an industrial scale.
Also already proposed and applied for practical use as optical recording media are recording media each having an inorganic recording film layer made of a low melting point metal such as Te, Te alloys or Bi alloys.
However, production efficiency of such a recording medium having an inorganic recording film layer is low since the recording film layer must be formed by vacuum evaporation, or sputtering and there is a problem in recording density since the thermal conductivity of the recording film layer is high. Furthermore, since a harmful metal is used to prepare a recording medium having such an inorganic recording film layer, it is essential to overcome the problems concerning operation environment and waste water disposal.
In order to solve these problems, various proposals have been made to use phthalocyanine pigments which are known as blue to green pigments and excellent in stability as materials for optical recording media, specific examples being copper phthalocyanine, lead phthalocyanine, titanium phthalocyanine, vanadyl phthalocyanine and tin phthalocyanine (Unexamined Japanese Patent Publication Nos. 36490/1983 and 11292/1984). However, these pigments are inferior in matching with the semiconductor lasers, which are commonly used as the recording lasers at the present day, having oscillation wavelengths at approximately 780 to 830 nm, since they have maximum absorption wavelengths in the vicinity of 700 nm.
Under these circumstances, although there is proposed a process in which the absorption wavelengths are shifted to the long wavelenth region by means of processing with organic solvents or heating treatment, such a process has not yet been applied for practical use since these metal phthalocyanine pigments are scarcely soluble in organic solvents, in addition to complicated processing steps, so that it is impossible to form a thin film on a substrate made of a thermoplastic resin substrate, such as polycarbonate by coating solutions thereof and it is inevitable to use vacuum evaporation coating or sputtering technique.
In order to solve various problems described above, an optical recording medium has been proposed, in which a soluble organic pigment is used to form a recording film layer on a substrate by coating. More specifically, developed and applied for practical use is an optical recording medium which is formed by spin coating an organic pigment which has an absorption wavelength within the oscillation wavelengths of semiconductor lasers and is soluble in organic solvents, more specific examples of such a pigment being dithiol-metal
REFERENCES:
CA:106: 166306m "Laser-Sensitive" optical recording medium (1987).
Hayashida et al., Chemistry Letters, The Chemistry Society of Japan, pp. 2137-2140, 1990.
Wheller et al., J. Am. Chem. Soc., 106:7404-7410, 1984.
Kovshev et al., Zh. Obshch. Khim., 42:696-699, 1972.
Firey et al., J. Am. Chem. Soc., 110:7626-7630, 1988.
Hayashi Nobuyuki
Katayose Mitsuo
Mitani Motohiro
Morishita Yoshii
Nakayama Masaharu
Hitachi Chemical Co. Ltd.
Nippon Oil and Fats Co. Ltd.
Page Thurman K.
Venkat Jyothsna
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