Electric lamp and discharge devices – With luminescent solid or liquid material
Reexamination Certificate
2002-11-22
2004-06-15
Lambkin, Deborah C (Department: 1626)
Electric lamp and discharge devices
With luminescent solid or liquid material
C359S326000, C359S237000, C385S002000, C385S122000, C385S141000, C430S630000
Reexamination Certificate
active
06750603
ABSTRACT:
All patents, patent applications, and publications cited within this application are incorporated herein by reference to the same extent as if each individual patent, patent application or publication was specifically and individually incorporated by reference.
BACKGROUND OF THE INVENTION
The invention relates generally to the organic chromophores for second order nonlinear optical (NLO) applications, compositions including such chromophores, and applications including such chromophores and compositions.
The development and uses of NLO chromophores, including polymer matrix development, waveguide fabrication, and optical device fabrication are well documented. An NLO chromophore (also known as a “push-pull” chromophore) comprises three fundamental building blocks represented by the general formula D-&pgr;-A, where D is a donor, &pgr; is a &pgr;-bridge, and A is an acceptor. In the art, a “&pgr;-bridge” is sometimes referred to as a “&pgr;-conjugated bridge,” “&pgr;-electron bridge,” “conjugated &pgr;-electron bridge,” and the like. Examples of such bridges are described, for example, in U.S. Pat. Nos. 5,670,091, 5,679,763, 6,067,186, and 6,090,332. A “&pgr;-bridge” allows charge transfer from a donor to an acceptor in a chromophore. Exemplary acceptors are shown in
FIG. 1
, where, independently at each occurrence, R
1
is hydrogen, a halogen except when bonded to a carbon alpha to or directly to a nitrogen, oxygen, or sulfur atom, or an alkyl, aryl, heteroalkyl, or heteroaryl group; Y is O, S or Se; and q is 0 or 1. Exemplary donors are shown in
FIG. 2
, where, independently at each occurrence, R
1
is hydrogen, a halogen except when bonded to a carbon alpha to or directly to a nitrogen, oxygen, or sulfur atom, or an alkyl, aryl, heteroalkyl, or heteroaryl group; R
2
is hydrogen or an alkyl, aryl, heteroalkyl, or heteroaryl group; Y is O, S or Se; m is 2, 3 or 4; p is 0, 1 or 2; and q is 0 or 1. Herein, a heteroalkyl group includes, but is not limited to, functional groups, halogen substituted alkyl groups, perhalogenated alkyl groups, and dendrons. What is meant by a functional group in generally understood in the art of organic chemistry, for example see Appendix B in Jerry March, “Advanced Organic Chemistry” 4
th
Edition, John Wiley and Sons, New York, pp 1269-1300. A “dendron” is a substituent that has regularly repeating subunits. A dendron may be further comprised of one or more heteroaryl group. A “dendrimer” is a macromolecular structure that contains a “core” surrounded by one or more dendrons. Often in the art, the terms dendron and dendrimer are used interchangeably. Dendrons and dendrimers are illustrated and discussed in Bosman et al.,
Chem. Rev.
1999, 99, 1665 and U.S. Pat. No. 5,041,516.
The particular D-&pgr;-A arrangement affects the ability of the molecule to achieve large second order NLO effects. Thus, the first molecular electronic hyperpolarizability (&bgr;, sometimes given as &mgr;&bgr;, where &mgr; is the dipole moment of the chromophore), which is a measure of this ability, can be tuned and optimized by changing the electronic properties of any one of D, &pgr;, or A, see Gorman and Marder
Proc. Natl. Acad. Sci, USA
1993, 90, 11297. Molecular NLO effects, in turn, can be translated into bulk EO activity in a material by aligning molecules in one direction by applying an electric field.
SUMMARY OF THE INVENTION
In one aspect, a nonlinear optical chromophore has the formula D-&pgr;-A where &pgr; is a &pgr; bridge including a thiophene ring having oxygen atoms bonded directly to the 3 and 4 positions of the thiophene ring, D is a donor, and A is an acceptor. The oxygens bonded directly to the 3 and 4 ring positions of the of the thiophene ring may be further independently substituted with an alkyl group comprising 1 to about 20 carbons, a heteroalkyl group comprising 1 to about 20 carbons, an aryl group comprising 1 to about 20 carbons, or a heteroaryl group comprising 1 to about 20 carbons.
In a second aspect, a nonlinear optical chromophore has the formula:
wherein, independently at each occurrence: &pgr;
1
is absent or a &pgr;-bridge; &pgr;
2
is absent or a &pgr;-bridge; D is an donor; A is an acceptor; X is O or S; and R is an alkyl group comprising 1 to about 20 carbons, a heteroalkyl group comprising 1 to about 20 carbons, an aryl group comprising 1 to about 20 carbons, or a heteroaryl group comprising 1 to about 20 carbons. These chromophores may be combined with a polymer matrix to form second order nonlinear optical compositions useful in a variety of applications, including electro-optic devices such as optical modulators, optical switches, and optical directional couplers. For example, the chromophore and polymer matrix may contain crosslinkable functional groups, and may be combined to form a guest-host composite, in which the chromophore is the guest and the polymer matrix is the host. An electric field is then applied to the composite to induce electro-optic activity, after or during which the composite is crosslinked to covalently bond the chromophore to the polymer matrix. Other features and advantages of the invention will be apparent from the following description of preferred embodiments thereof, and from the claims.
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Chen Baoquan
Huang Diyun
Fish & Richardson P.C. P.A.
Lambkin Deborah C
Lumera Corporation
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