Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1996-12-24
1998-05-26
McKane, Joseph
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
548198, 548136, 548143, 549 68, 549 74, 558406, 558409, C07D27728, C07D33306
Patent
active
057567530
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP95/02328 filed Jun. 16, 1995.
The present invention relates to the use of methine or azamethine dyes based on naphthoquinones in nonlinear optics and to novel methine dyes.
The nonlinear optical properties of organic compounds find application in many areas of optoelectronics. Examples are applications in frequency doubling, phase modulators, optical amplifiers, interferometers, optical switches or communications technology.
It is common knowledge that organic materials, in particular polymers with specific chromophores, can have nonlinear optical properties which in some instances are more considerable than those of comparable inorganic materials.
The materials currently most frequently used are inorganic crystals, for example of potassium dihydrogenphosphate or lithium niobate. These crystals are complicated and costly to produce and, owing to their rigid structure, difficult to use in optical apparatus. A further disadvantage are their small nonlinear effects.
A particular advantage of suitable organic chromophores and their use in polymeric materials is their simple preparation and processing.
The chromophores used in nonlinear optics are generally used either in crystalline form or in polymer-bound form.
DE-A-3 904 797, EP-A-312 856 and EP-A-572 898 disclose the use of dyes in polymeric nonlinear optical systems.
It is an object of the present invention to provide suitable methine or azamethine dyes based on naphthoquinones which shall be advantageously used in polymeric nonlinear optical systems. More particularly, such dyes shall have large hyperpolarizability values, good thermal stability, good compatibility with the polymers used in nonlinear optical systems, and good film-forming properties with copolymers.
We have found that this object is achieved by naphthalene derivatives of the formula I ##STR2## where the rings A and B may each be benzofused, X is CH.dbd.CH--CH, a 5- or 6-membered aromatic carbocyclic radical, and C.sub.1 -C.sub.4 -alkyl or C.sub.5 -C.sub.7 -cycloalkyl, in nonlinear optics. benzene, thiophene, thiazole, oxadiazole or thiadiazole series.
Particularly suitable radicals Z include for example those of the formulae IIIa to IIIf ##STR3## where the ring K may be benzofused, -C.sub.10 -alkyl which may be phenyl-, hydroxyl-, acryloyloxy- or methacryloyloxy-substituted, or phenyl, or L.sup.1 and L.sup.2 are together with the nitrogen atom joining them together pyrrolidinyl, piperidinyl, morpholinyl, piperazinyl or N-(C.sub.1 -C.sub.4 -alkyl)piperazinyl, -C.sub.10 -alkyl, C.sub.5-C.sub.7 -cycloalkyl, C.sub.1 -C.sub.10 -alkoxy, cyano or halogen, and hydroxyl-, acryloyloxy- or methacryloyloxy-substituted, C.sub.5 -C.sub.7 -cycloalkyl, phenyl, C.sub.1 -C.sub.10 -alkoxy, cyano, nitrogen or halogen.
Any alkyl appearing in the abovementioned formulae may be straight-chain or branched.
In any substituted alkyl appearing in the abovementioned formulae the number of substituents is generally 1 or 2. are each for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl. pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl or isodecyl (the above designations isooctyl, isononyl and isodecyl are trivial names derived from the oxo process alcohols--cf. Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. A1, pages 240 to 293, and Vol. A10, pages 284 to 285). for example cyclopentyl, cyclohexyl or cycloheptyl. propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, hexyloxy, 2-methylpentyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, isooctyloxy, nonyloxy, isononyloxy, decyloxy, isodecyloxy, fluorine, chlorine, bromine or iodine. 2-phenylethyl, 2-hydroxyethyl, 2-hydroxypropyl, 3-hydroxypropyl, 2-hydroxybutyl, 4-hydroxybutyl, 5-hydroxypentyl, 6-hydroxyhexyl, 7-hydroxyheptyl, 8-hydroxyoctyl, 9-hydroxynonyl, 10-hydroxydecyl, 2-acryloyloxyethyl, 2-methacryloyloxyethyl, 2- or 3-acryloyloxypropyl, 2- or 3-metha
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Beckmann Stefan
Etzbach Karl-Heinz
Sens Rudiger
BASF - Aktiengesellschaft
McKane Joseph
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