Indolizinetrimethine dyes

Details Indolizinetrimethine dyes Indolizinetrimethine dyes

1993-07-20

1994-08-16

Ivy, C. Warren

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

430495, 430945, C07D40104

Patent

active

053388488

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to novel indolizinetrimethine dyes of the general formula I ##STR2## where the variables are defined as follows: R.sup.1 is C.sub.1 -C.sub.22 -alkyl which may be substituted by halogen, hydroxyl, C.sub.1 -C.sub.6 -alkoxy, benzyloxy, C.sub.1 -C.sub.6 -alkanoyl, C.sub.1 -C.sub.6 -alkoxycarbonyl or phenyl, C.sub.3 -C.sub.7 -cycloalkyl, which may be substituted by halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy, or phenyl which may be substituted by halogen, hydroxyl, cyano, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, carboxyl, C.sub.1 -C.sub.6 -alkoxycarbonyl or hydroxysulfonyl, C.sub.1 -C.sub.22 -alkyl may be interrupted by from one to five oxygen atoms in ether function, recording media which contain dyes I.
Recording media which on high-energy irradiation undergo a local change of state are known. This thermally initiated change of state, e.g. vaporization, altered flow behavior or bleaching, is accompanied by a change in optical properties, for example in the absorption through a shift in the absorption maximum or absorbance, which can be utilized for information or data recording.
Suitable light sources for optical recording include inter alia semiconductor lasers which emit light in the near infrared. Of particular suitability here are solid state injection lasers, in particular the AlGaAs laser, which emits within the wavelength range of about 700-900 nm.
The use of this laser is particularly advantageous on account of the small size of the unit, its low energy requirements and the possibility of direct modulation of the optical output through modulation of the electric drive current.
The recording media used must meet the following requirements: the dyes present in the media should be highly absorbing within the desired wavelength range, they should be readily accessible industrially, and be stable to outside influences and readily soluble in alcohols and polymers, so that they can be made, for example by the spin coating process, into thin, homogeneous dye layers of high background reflectivity which are firmly adherent on the customary support materials. Moreover, the recording media should be writable and subsequently readable with a semiconductor laser and have a high signal-to-noise ratio.
The dyes hitherto used for optical recording media are frequently deficient in one of the requirements mentioned. This is also true of the indolizinetrimethine dyes known from JP-A-227 693/1987 and DE-A-39 28 758, which differ from the compounds I in particular in the nature of the substituents in the 3-position of the indolizine ring.
It is an object of the present invention to find optical recording media dyes which come particularly close to meeting the required property profile.
We have found that this object is achieved by the indolizinetrimethine dyes I defined at the beginning.
We have also found optical recording media for recording and reproducing information items by means of laser bees, which contain these dyes in the laser light-sensitive layer.
Preferred embodiments of the invention are revealed in subclaims.
Suitable R.sup.1 and R.sup.2 radicals here are C.sub.1 -C.sub.22 -alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl and docosyl and also branched radicals of this kind, of which the alkyl groups of up to 12 carbon atoms are preferred and those of up to 8 carbon atoms are particularly preferred.
The alkyl groups mentioned may carry halogen such as fluorine, chlorine and bromine, hydroxyl, C.sub.1 -C.sub.6 -alkoxy, benzyloxy, C.sub.1 -C.sub.6 -alkanoyl, C.sub.1 -C.sub.6 -alkoxycarbonyl or phenyl as substituents, which are preferably in the .omega.-position. Under this definition, .omega.-bromo- and -hydroxy-C.sub.1 --C.sub.12 -alkyl groups are particularly preferred. Examples of t

REFERENCES:
patent: 3260601 (1966-07-01), Bailey
patent: 3398145 (1968-08-01), Bedley
patent: 3660085 (1972-05-01), Depoorter
patent: 4663261 (1987-05-01), Franke
Katritzky, Advances in Heterocyclic Chemistry, vol. 23, p. 103-104 and 134-135, 1978.
Research Disclosure, Oct. 1980, pp. 425-427.
Chemical Abstracts, AN 318601, JP-A-6 2227 693, Oct. 6, 1987.
Advances in Heterocyclic Chemistry, vol. 23, 1978, F. J. Swinbourne, et al., "Advances in Indolizine Chemistry", pp. 104-105 and 134-135.

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