Chromophores for polymeric thin films and optical waveguides...

Details Chromophores for polymeric thin films and optical waveguides... Chromophores for polymeric thin films and optical waveguides...

2000-09-29

2002-05-21

Lee, John D. (Department: 2874)

Optical waveguides

Planar optical waveguide

Thin film optical waveguide

C385S143000, C252S582000, C428S412000, C428S423100, C428S473500

Reexamination Certificate

active

06393190

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to chromophores which can be used in the preparation of polymeric thin films for waveguide media, and to optical waveguides and devices comprising the chromophores.
BACKGROUND OF THE INVENTION
Thin films of organic or polymeric materials with large second order nonlinearities in combination with silicon-based electronic circuitry can be used in systems for laser modulation and deflection, information control in optical circuitry, as well as in numerous other waveguide applications. In addition, novel processes through third order nonlinearity such as degenerate four-wave mixing, whereby real-time processing of optical fields occurs, have utility in such diverse fields as optical communications and integrated circuit fabrication. The utility of organic materials with large second order and third order nonlinearities for very high frequency application contrasts with the bandwidth limitations of conventional inorganic electrooptic materials currently in use.
Numerous optically responsive monomers and polymers have been developed for use in organic materials which, in turn, can be used in the waveguide applications described above. For example, U.S. Pat. No. 5,044,725, which is incorporated herein by reference in its entirety, describes numerous polymer compositions which provide suitable nonlinear optical response. U.S. Pat. No. 5,044,725 describes, for example, a preferred polymer composition comprising an organic chromophore containing an electron donating group and an electron withdrawing group at opposing termini of a bridge.
Synthesis of high performance organic, high &mgr;&bgr; electro-optic chromophores must be accomplished in order to make polymer-based electro-optic waveguides and devices. The synthesis of electro-optic chromophore bridge compounds and donor-bridge compounds for organic nonlinear optical applications are generally known in the art. Although some chromophores have been reported in the literature, many of them have shown several and sometimes severe problems ranging from thermal instability, insolubility in the polymer, photodegradability, exhibition of a broad absorption band into the wavelength region of interest, and large birefringence upon poling.
Most recently, U.S. Pat. No. 6,067,186 (the '186 patent), disclosed a class of organic chromophors which can result in hardened electro-optic polymers suitable for electro-optic modulators and other devices such as optical switch.
There continues to be a need for suitable electro-optic chromophores with improved properties.
SUMMARY OF THE INVENTION
The present invention is directed, in part, to compounds which can serve as chromophores in, for example, thin films for optical waveguides and optical devices. These are compounds represented by Formula I:
wherein:
D is an electron donating group;
B comprises at least one bivalent ring; and
R
2
and R
3
each, independently, are selected from the group consisting of substituted or unsubstituted C
2
-C
10
alkenyl, substituted or unsubstituted C
2
-C
10
alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted carbocycle, substituted or unsubstituted heterocycle, substituted or unsubstituted cyclohexyl, and (CH
2
)
n
—O—(CH
2
)
n
where n is 1-10. Alternatively, R
2
and R
3
can be selected from substituted or unsubstituted C
2
-C
10
alkyl, provided that when R
2
and R
3
are both selected from substituted or unsubstituted C
1
-C
1
alkyl the following condition is also met: R
2
≠R
3
. More preferably, chromophores of the invention have Formula I′:
 where:
R
2
and R
3
are further characterized in that they define a ring in which * denotes a spiro junction, or where * denotes a chiral center; D and B have the definitions given above; and R
2
and R
3
each, independently, are either, substituted or unsubstituted C
1
-C
10
alkyl, substituted or unsubstituted C
2
-C
10
alkenyl, substituted or unsubstituted C
2
-C
10
alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted carbocyclic, substituted or unsubstituted heterocyclic, substituted or unsubstituted cyclohexyl, or (CH
2
)
n
—O—(CH
2
)
n
, where n is 1-10.
In still another aspect of the invention, the chromophores comprise novel cyclic bridges comprising at least one bivalent aromatic ring. Preferred compounds of the invention have Formula II:
wherein D is an electron donating group; A is an electron withdrawing group; K is O or S;
R
1
is —Q—C
n
H
2n+1
, —Q—(CH
2
)
a
CC
n
F
2n+1
, —Q—CH
2
OCH
2
C
n
F
2n+1
, —Q—CH
2
SCH
2
CC
n
F
2n+1
, —Q—CH
2
OCH
2
CF
3
, or —Q—CH
2
SCH
2
CF
3
, where n is 1-10, a is 0-10, and Q is absent, O or S; and q is 1, 2, or 3.
Other preferred compounds of the invention have Formula III:
wherein D is an electron donating group; A is an electron withdrawing group; J is CH
2
, O or S; R
1
is —Q—C
n
H
2n+1
, —Q—(CH
2
)
a
C
n
F
2n+1
, —Q—CH
2
OCH
2
C
n
F
2n+1
, —Q—CH
2
SCH
2
CC
n
F
2n+1
, —Q—CH
2
OCH
2
CF
3
, or —Q—CH
2
SCH
2
CF
3
, where n is 1-10, a is 0-10, and Q is absent, O or S.
In other embodiments of the invention, the chromophores comprise novel cyclic bridges comprising at least one bivalent or conjugated ring structure, such as an aromatic ring, and novel electron withdrawing groups. Such compounds are generally represented by the structure of Formula IV:
wherein D is an electron donating group; K is O or S; R
1
is —Q—C
n
H
2n+1
, —Q—(CH
2
)
a
C
n
F
2n+1
, —Q—CH
2
OCH
2
C
n
F
2n+1
, —Q—CH
2
SCH
2
CC
n
F
2n+1
, —Q—CH
2
OCH
2
CF
3
, or —Q—CH
2
SCH
2
CF
3
, where n is 1-10, a is 0-10, and Q is absent, O or S; q is 1, 2, or 3; and R
2
and R
3
each, independently, are either substituted or unsubstituted C
1
-C
10
alkyl, substituted or unsubstituted C
2
-C
10
alkenyl, substituted or unsubstituted C
2
-C
10
alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted carbocycle, substituted or unsubstituted heterocycle, substituted or unsubstituted cyclohexyl, or (CH
2
)
n
—O—(CH
2
)
n
where n is 1-10. Alternatively, R
2
and R
3
together form a ring structure or a substituted ring structure. Preferred compounds of this embodiment are represented by the structure of Formula IV′:
 where:
R
2
and R
3
are further characterized in that they define a ring in which * denotes a spiro junction, or where * denotes a chiral center.
Other useful compounds of the invention have Formula V:
wherein D is an electron donating group; J is CH
2
, O or S; R
1
is —Q—C
n
H
2n+1
, —Q—(CH
2
)
a
C
n
F
2n+1
, —Q—CH
2
OCH
2
C
n
F
2n+1
, —Q—CH
2
SCH
2
CC
n
F
2n+1
, —Q—CH
2
OCH
2
CF
3
, or —Q—CH
2
SCH
2
CF
3
, where n is 1-10, a is 0-10, and Q is absent, O or S; and R
2
and R
3
each, independently, are either H, substituted or unsubstituted C
1
-C
10
alkyl, substituted or unsubstituted C
2
-C
10
alkenyl, substituted or unsubstituted C
2
-C
10
alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted alkylaryl, substituted or unsubstituted carbocycle, substituted or unsubstituted heterocycle, substituted or unsubstituted cyclohexyl, or (CH
2
)
n
—O—(CH
2
)
n
where n is 1-10. Alternatively, R
2
and R
3
together form a ring structure or a substituted ring structure. Preferred chromophores of this embodiment include compounds of Formula (V′):
where:
R
2
and R
3
are further characterized in that they define a ring in which * denotes a spiro junction, or where * denotes a chiral center.
The present invention is also directed to optical waveguides comprising a thin film medium having Formula VI:
wherein P and P′ are polymer main chain units, which can be the same mer unit or different mer unit, and C is a comonomer unit where n is an integer greater than zero and n′ is 0 or an integer greater than zero; S is a pendant spacer group having a linear chain length of between about 2-12 atoms. M is a compound having either Formula I,

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