Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Patent
1996-10-15
1998-07-07
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
534775, 534791, 534794, 548193, 548194, 549 61, 549 68, 8691, 8662, 106 3145, 106 315, 106 3151, 385130, 359321, C09B 29033, C09B 29042, C07D33338, G02F 135
Patent
active
057770891
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP 95/01290 filed Apr. 7, 1995.
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to phenol derivatives, processes for their preparation, polymers which contain these phenol derivatives as monomers and their use, in particular in nonlinear optics.
2. Discussion of the Invention
The nonlinear optical properties of organic compounds are utilized in many areas of optoelectronics. Examples of this are applications in frequency doubling, phase modulators, optical amplifiers, interferometers or optical switches and communications engineering.
It is generally known that organic materials, in particular polymers having special chromophores, may have nonlinear optical properties which in some cases are more pronounced than those of comparable inorganic materials.
The most frequently used materials at present are inorganic crystals, for example those of potassium dihydrogen phosphate or lithium niobate. These crystals are prepared by a complicated and expensive process and, owing to their rigid structure, can be used in optical apparatuses only with difficulty.
One 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 employed as a rule in either crystalline or polymer-bound form.
Angew. Chem., 96 (1984), 637-651 discloses the use of stilbene derivatives or special azo dyes for this purpose.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide suitable phenol derivatives which are advantageous in particular for use in polymeric nonlinear optical systems. In particular, these phenol derivatives or dyes which can be derived therefrom should have large hyperpolarizability values, good heat stability, good compatibility with the polymers used in nonlinear optical systems and good film formation properties with copolymers.
We have found that this object is achieved by phenol derivatives of the general formula I ##STR2## where R.sup.1 and R.sup.2, independently of one another, are hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.1 -C.sub.10 -alkoxy, OH, NR.sup.5 R.sup.6, CN, NO.sub.2, halogen, CHO, ##STR3## X is N or CR.sup.4, Y is a chemical bond, S, ##STR4## SO.sub.2, O or NR.sup.6, Z is hydrogen, acryloyl or methacryloyl, component, or ##STR5## R.sup.4 is hydrogen, CN, NO.sub.2 or CO.sub.2 R.sup.5, R.sup.5 is hydrogen, alkyl, cycloalkyl, unsubstituted or substituted phenyl, benzyl or alkoxy, C.sub.1 -C.sub.10 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl or C.sub.1 -C.sub.6 -alkoxy which is unsubstituted or substituted by phenyl or by C.sub.1 -C.sub.4 -alkoxy, and group, where R.sup.8 and R.sup.9 together with the nitrogen atom linking them may form a ring.
The present invention furthermore relates to a process for the preparation of certain phenol derivatives, and the use of these phenol derivatives in nonlinear optics, for coloring textiles or for thermal transfer printing.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
Phenol derivatives of the formula I, where Y is a chemical bond and/or X is CR.sup.4, are particularly suitable according to the invention.
Phenol derivatives of the formula I, where -cycloalkyl, C.sub.1 -C.sub.10 -alkoxy, OH, halogen or CHO and ##STR6## are also particularly suitable according to the invention.
In a preferred embodiment of the invention, R.sup.3 is NH.sub.2. Very particularly preferred phenol derivatives are of the formula II ##STR7##
These compounds are particularly suitable as intermediates for the preparation of novel phenol derivatives of the formula I, where R.sup.3 is ##STR8## These are directly useful for applications in nonlinear optics.
Suitable radicals G are, for example, ##STR9## where L.sup.1 and L.sup.2 are identical or different and, independently of one another are each hydrogen or unsubstituted or substituted C.sub.1 -C.sub.6 -alkyl which may be interrupted by 1 or 2 ether oxygen atoms, or are each C.sub.5 -C.sub.7 -cycloalkyl
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Beckmann Stefan
Etzbach Karl-Heinz
Sens Rudiger
BASF - Aktiengesellschaft
Powers Fiona T.
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