Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1999-02-09
2000-07-11
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
540132, 540129, 540 132, 540136, 540139, 540140, 528 641, 430270, 430495, G03C 192, G03C 506, G01D 900, C07D48722
Patent
active
060874929
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP97/05223 filed Sep. 24, 1997.
This invention relates to novel phthalocyanines or the derivatives thereof which are substituted by 1-4 formyl, carbonyl, hydroxymethyl or carboxyl groups, to their use in recording layers of optical recording media, as well as to a novel process for the preparation of some of these compounds.
The field of this invention is that of the optical recording of information on write-once recording media, the information bits differing in the different optical properties of a dye on written or unwritten places. This technology is usually called WORM (for example CD-R, SD-R, DVD-R or MMCD-R), which abbreviations have been adopted here.
The use of dyes which absorb radiation in the near infrared range (NIR range) for recording information in WORM systems (write once read many) has been known for some time and has been described, inter alia, by Emmelius in Angewandte Chemie, No. 11, pages 1475-1502 (1989). By irradiating such recording materials with laser it is possible to achieve the change in absorption required for recording information in binary form via physical changes (for example by sublimation or diffusion) or via chemical changes (for example photochromism, isomerisation or thermal degradation).
Substituted phthalocyanines are an important class of dyes for use in such WORM systems because they have high NIR absorptions in the range of 700 nm to 900 nm when, depending on the central metal atom, they are correspondingly peripherally substituted.
The most stringent requirements are placed on the recording layer to be used, such as high refractive index, high initial reflectivity, narrow absorption bands in the solid state, uniformity of the writing width at different pulse duration, high stability to light in daylight as well as under weak laser radiation (readout) coupled with high sensitivity to intense laser radiation (inscribing), low noise, high resolution as well as, most importantly, very little statistical jitter of the pits over a desired value at optimum writing performance.
As the recording layer is normally applied from a solution, typically by spin coating, the dyes must usefully be readily soluble in conventional solvents, which are described, inter alia, in EP 511 598.
Alkoxy-polysubstituted and halogenated phthalocyanines are known from EP 373 643 and EP 513 370. However, such compounds cannot be used singly but only as mixtures of many isomers. Analogous isomer mixtures having improved sufficient solubility are known from EP 703 280.
On the other hand, EP 712 904 discloses phthalocyanines substituted by phosphorus groups which have a low degradation temperature, a relatively narrow absorption band and a high refractive index at 780 nm and good contrast between written and unwritten places.
However, the known recording layers with readily soluble phthalocyanine dyes have the required properties only to an unsatisfactory extent, the optical resolution in particular often being not quite satisfactory. Moreover, the best products are noble metal phthalocyanines, the high material costs of which are irreconcilable with the demand for an inexpensive mass product which may be thrown into the rubbish.
Moreover, as the known soluble products are exclusively complicated isomer mixtures, it is imperative to use an extremely elaborate analytics for quality control.
Using specific phthalocyanine derivatives as recording layer, it has surprisingly been possible to provide an optical recording medium, the properties of which are astonishingly better than those of the recording media known to date. In addition, the phthalocyanine derivatives of this invention can be easily analysed and it is not necessary to choose a noble metal as central metal atom.
In one of its aspects, this invention relates to a phthalocyanine or its metal complex of a divalent metal, oxometal, halogenometal or hydroxymetal, which comprises at least one unsubstituted or substituted formyl, carbonyl, hydroxymethyl or carboxyl group attached at the peripheral carbon skele
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Ciba Specialty Chemicals Corporation
Crichton David R.
Shah Mukund J.
Sripada Pavanaram K
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