Compositions – Light transmission modifying compositions
Patent
1996-05-08
1998-04-14
Wu, Shean C.
Compositions
Light transmission modifying compositions
354752, 354753, 526256, 526257, 526312, F21V 900, C08F22806, C09B 29033
Patent
active
057388067
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP44/03685 filed on Nov. 9, 1994.
DESCRIPTION
The present invention relates to the use in nonlinear optics of azo dyes having a diazo component derived from an aminothienothiophene and a coupling component of the aniline series, to polymers derived from these azo dyes, to the use thereof in nonlinear optics, and to novel phenylthienothienylazoanilines.
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 certain chromophores, can have nonlinear optical properties which are in some instances more considerable than those of comparable inorganic materials. The materials currently used most frequently 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 equipment. A further disadvantage is the smallness of their 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.
Angew. Chem. 96 (1984), 637-651, discloses the use of stilbene derivatives or specific azo dyes for this purpose.
It is an object of the present invention to provide suitable thienothienylazo dyes which are advantageous for use in polymeric nonlinear optical systems. More particularly, such azo compounds 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 azo dyes of the formula I ##STR1## where the ring A may be benzofused, unsubstituted or phenyl-, hydroxyl-, acryloyloxy- or methacryloyloxy-substituted C.sub.1 -C.sub.10 -alkyl, 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, carbamoyl, dicyanovinyl or a radical of the formula COX.sup.1, COOX.sup.1, CONX.sup.1 X.sup.2, CH.dbd.N--X.sup.3, CH.dbd.C(NO.sub.2)--X.sup.4 or ##STR2## where X.sup.1 and X.sup.2 are each independently of the other C.sub.1 -C.sub.10 -alkyl, which may be phenyl-substituted, C.sub.5 -C.sub.7 -cycloalkyl or phenyl, X.sup.3 is hydroxyl or phenylamino, X.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl, and X.sup.5 is hydrogen, nitro, hydroxysulfonyl, formyl, cyano, C.sub.1 -C.sub.4 -alkylsulfonyl, dicyanovinyl or a radical of the formula COX.sup.1, COOX.sup.1, CONX.sup.1 X.sup.2, CH.dbd.N--X.sup.3 or CH.dbd.C(NO.sub.2)--X.sup.4, where X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are each as defined above, and the ring A and L.sup.3 and L.sup.4 are each as defined above, COX.sup.1, COOX.sup.1 or CONX.sup.1 X.sup.2, where X.sup.1 and X.sup.2 are each as defined above, and phenyl-substituted, C.sub.5 -C.sub.7 -cycloalkyl, phenyl or C.sub.1 -C.sub.10 -alkoxy,
Any alkyl appearing in the abovementioned formula I may be straight-chain or branched.
In substituted alkyl appearing in the abovementioned formula I the number of substituents is generally 1 or 2.
L.sup.1, L.sup.2, L.sup.3, L.sup.4, X.sup.1, X.sup.2, X.sup.4 and R.sup.3 are each for example methyl, ethyl, propyl, isopropyl, butyl, isobutyl or sec-butyl.
L.sup.1, L.sup.2, L.sup.3, L.sup.4, X.sup.1, X.sup.2 and R.sup.3 may each also be for example 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 der
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Angew. Chem. 96 (1984) 637-651, Von David J. Williams.
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Chemistry and Industry, 1990, pp. 600 to 608.
Beckmann Stefan
Etzbach Karl-Heinz
Sens Ruediger
BASF - Aktiengesellschaft
Wu Shean C.
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