Diphenylamine compounds, polymers prepared therefrom and non-lin

Details Diphenylamine compounds, polymers prepared therefrom and non-lin Diphenylamine compounds, polymers prepared therefrom and non-lin

1996-04-19

1997-12-09

Higel, Floyd D.

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

Organic compounds

Azo

252582, 526218, 534752, 534795, 534829, 534852, 534860, 558401, C09B 29033, C09B 29048, C09B 29042, C07C24508, C07C25500, C08F 404

Patent

active

056962436

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to novel diphenylamines of the formula I ##STR2## where the ring A can be benzo-fused, and three hetero atoms selected from the group consisting of nitrogen, oxygen and sulfur, in the heterocyclic ring and can be fused to a benzene, thiophene, pyridine or pyrimidine ring, is 1,2,2-tricyanovinyl, each hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy or halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, halogen, prop-1-en-3-yl, acryloyl, methacryloyl or oxiranylmethoxy, and optics.
DE-A-4 213 155 describes azo dyes having a diazo component from the aniline series and a coupling component from the N-benzyl- or N-phenylethylaniline series, homopolymers or copolymers thereof, and their use in nonlinear optics.
Furthermore, Angew. Chem., 96 (1984), 637 to 651, discloses the use of stilbene derivatives or specific azo dyes for this purpose.
It is an object of the present invention to provide novel compounds based on stilbene derivatives, tricyanovinylbenzenes and aryl- or hetarylazobenzenes or -naphthalenes which are advantageously suitable for use in nonlinear optical systems. In particular, these compounds should have high hyperpolarizability values and should be stable to heat and oxidation. The compounds should also be polymerizable, and the systems obtained from them should have a high glass transition temperature.
We have found that this object is achieved by the diphenylamines of the formula I described in greater detail in the introduction.
Preference is given to diphenylamines of the formula I in which D is aryl or heterocyclyl selected from the series consisting of pyrrolyl, furanyl, thiophenyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, benzofuranyl, benzothiophenyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzisothiazolyl, pyridothiophenyl, pyrimidothiophenyl and thienothiazolyl.
Particular preference is given to diphenylamines of the formula I in which D is aryl or heterocyclyl from the series consisting of pyrrolyl, thiophenyl, pyrazolyl, thiazolyl, isothiazolyl, triazolyl, thiadiazolyl, benzothiophenyl, benzothiazolyl, benzisothiazolyl, pyridothiophenyl, pyrimidothiophenyl and thienothiazolyl.
Particular importance is attached to diphenylamines of the formula I in which
D is ##STR3## where L.sup.1 is nitro, cyano, C.sub.1 -C.sub.6 -alkanoyl, benzoyl, C.sub.1 -C.sub.6 -alkylsulfonyl, substituted or unsubstituted phenylsulfonyl or --CH.dbd.T, where T is hydroxyimino, C.sub.1 -C.sub.4 -alkoxyimino or a radical of a CH-acidic compound, unsubstituted or phenyl- or C.sub.1 -C.sub.4 -alkoxy-substituted C.sub.1 -C.sub.6 -alkoxy, unsubstituted or substituted phenoxy, unsubstituted or phenyl-substituted C.sub.1 -C.sub.6 -alkylthio, unsubstituted or substituted phenylthio, C.sub.1 -C.sub.6 -alkylsulfonyl or unsubstituted or substituted phenylsulfonyl, -C.sub.6 -alkanoyl, thiocyanato or halogen, -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.6 alkylsulfonyl, substituted or unsubstituted phenylsulfonyl or --CH.dbd.T, where T is as defined above, or phenyl- or C.sub.1 -C.sub.4 -alkoxy-substituted C.sub.1 -C.sub.6 -alkoxy, unsubstituted or phenyl-substituted C.sub.1 -C.sub.6 -alkylthio, unsubstituted or substituted phenylthio, C.sub.1 -C.sub.6 -alkylsulfonyl, unsubstituted or substituted phenylsulfonyl or C.sub.1 -C.sub.4 -alkoxycarbonyl, -alkyl, unsubstituted or phenyl-substituted C.sub.1 -C.sub.6 -alkylthio, unsubstituted or substituted phenyl, thienyl, C.sub.1 -C.sub.4 -alkylthienyl, pyridyl or C.sub.1 -C.sub.4 -alkylpyridyl, unsubstituted or phenyl-substituted C.sub.1 -C.sub.6 -alkylthio or C.sub.1 -C.sub.6 -dialkylamino, -C.sub.4 -alkoxycarbonyl)ethylthio, halogen, and 1,2,2-tricyanovinyl or E--N.dbd.N, where E is phenyl which is substituted by cyano, nitro, 2,2-dicyanovinyl or 1,2,2-tricyanovinyl, and
All the alkyl and alkylene groups which occur in the above formulae I and II may be either straight-chain or branched.
If the above formulae I and II contain any substituted phenyl groups, example

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