Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1990-04-02
1992-10-13
Raymond, Richard L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
519491, 519479, 519480, 519 72, 548530, 548558, 548561, 549 68, C07D30312, C07D30738
Patent
active
051552329
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to an organic material for non-linear optics.
Materials having non-linear properties in optics may be used for numerous applications: frequency doublers; optical bistables; switches; modulators; directional couplers; parametric amplifiers; etc.
A small number of inorganic materials which are non-isotropic, and in particular non-centrosymmetrical, are known which possess a non-zero second order coefficient and non-linear optical properties. These include in particular potassium-dihydrogen-phosphate (KDP), and lithium niobate and tantalate (LiNbO.sub.3, LiTaO.sub.3, . . . ).
It is often difficult to make these inorganic materials. That is why interest has been shown in organic materials having non-linear properties, in particular when the materials are polymers, thermoplastic, or film-forming.
Optical non-linearity is generally obtained by incorporating highly hyperpolarizable polar molecules or groups of molecules in the organic material by mixing or by chemical grafting.
Such molecules are synthesized by associating an electron attractor group with an electron donor group via a group for transmitting electron effects.
For example, the following materials are known: ##STR1## N (nitro 4 phenyl) N methyl amino 2 acetonitrile (NPAN) ##STR2## dinitro 2-4 phenyl L alanine (MAP) ##STR3## methyl 3 nitro 4 pyridine N-oxide (POM) ##STR4##
These molecules are characterized by their coefficient of hyperpolarizability .beta. defined by the series development of the dipolar moment .mu. as a function of the electric field E
The coefficient .beta. may be measured by the EFISH method (Electric Field Induced Second Harmonic generation).
Many authors judge the value of a synthesized molecule on the basis of the value of its molecular hyperpolarizability associated with infrared frequency doubling.
For these applications, molecules having a large number of atoms may be suitable, however experience shows that such molecules absorb light strongly in the visible spectrum and this may be unacceptable. For electro-optical applications, the useful magnitude is rather hyperpolarizability per unit mass or per unit volume.
The object of the present invention is to find molecules having all the essential parts (attractor group, donor group, and transmitter group) using as small a number of atoms as possible, while nevertheless conserving a good value of constant field molecular hyperpolarizability.
The present invention provides an organic material for non-linear optics comprising an electron attractor group and an electron donor group interconnected by an electron effect transmitter group, the material being characterized by the fact that:
the electron donor group comprises an aromatic heterocycle in the form of a 5 member ring that includes a heteroatom selected from S, O, and N;
the electron attractor group is selected from NO.sub.2 and CN; and
the transmitter group is selected from the group consisting of carbon chains having n atoms of carbon (where n<4) and including a double or a triple bond, and an aromatic system such as a phenyl ring.
The nitrogen atom may be bonded to a radical R selected from H, CH.sub.3, and C.sub.2 H.sub.5.
In a first variant, the said transmitter group is constituted by an ethenyl bond.
By way of example, the material of the invention may satisfy one of the following formulas: ##STR5##
In a second variant, the said transmitter group is constituted by a phenyl ring. The material of the invention may then satisfy one of the following formulas: ##STR6##
In another variant, the said heteroaromatic cycle is substituted at 5 by a group selected from CH.sub.3 O, CH.sub.3 S, NH.sub.2, CH.sub.3 NH, (CH.sub.3).sub.2 N.
In all molecules of the invention, the electron donor characteristic and the aromatic characteristic are concentrated on a smaller number of atoms than in prior art molecules since they contain aromatic cycles which are rich in electrons (substituted or non-substituted furan, thiophene, or pyrrole).
With these molecules possessing a small number of atoms, it is possi
REFERENCES:
patent: 4174405 (1979-11-01), Relyea et al.
patent: 4863503 (1989-09-01), Anthony et al.
Marowsky et al., J. Opt. Soc. Am B, "Efficiency studies of second-harmonic-active organic dye coverages," 4(6), pp. 956-961 (1987).
Amatore Christian
Fauvarque Jean-Francois
Jutand Anny
Ratovelomanana Victorien
ALCATEL N.V.
Raymond Richard L.
Russell Mark W.
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