Compositions – Light transmission modifying compositions
Reexamination Certificate
2000-06-16
2003-02-04
Moore, Margaret G. (Department: 1712)
Compositions
Light transmission modifying compositions
C549S505000, C549S001000, C508S383000, C508S383000, C508S383000, C359S321000, C252S586000
Reexamination Certificate
active
06514434
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates generally to electro-optic chromophore bridge compounds and donor-bridge compounds which can be used in the preparation of chromophores for use in polymeric thin films for waveguide media, and specifically to organic nonlinear chromophore bridge compounds and donor-bridge compounds for polymeric switches and modulators.
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 applications contrasts with the bandwidth limitations of conventional inorganic electro-optic 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 structure 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 devices. The synthesis of electro-optic chromophore bridge compounds and donor-bridge compounds for organic nonlinear optical applications is generally known in the art. Although some bridge compounds and donor-bridge compounds have been reported in the literature, many of them have showed 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. Accordingly, suitable electro-optic chromophore bridge compounds and donor-bridge compounds are desired.
SUMMARY OF THE INVENTION
The present invention is directed to compounds which can serve as electro-optic chromophore bridge compounds for use in, for example, thin polymer films for waveguides. Preferred bridge compounds of the invention have Formula I.
Preferably, K is O or S. Preferably, R
1
is —Q—C
n
H
2n+1
, —Q—(CH
2
)
a
C
n
F
2n+1
, —Q—CH
2
SCH
2
C
n
F
2+1
, or —Q—CH
2
SCH
2
CF
3
, where n is 1-10 and a is 0-10, or —Q—CH
2
OCH
2
CF
3
. Other halogens or deuterium can be used in place of F. Q preferably is either absent or, when present, O or S. X preferably has the formula H or —(CH═CH)
b
C(═O)H, where b is 0-3. Z is a chemical group that is capable of being linked to a donor and includes, but is not limited to, Br, I, —CH
2
—Br, —CH
2
—OH, —CH
3
, —C(═O)H, —(CH═CH
2
)
n
where n is 1-3, and the like. Those skilled in the art can use additional groups known to those skilled in the art to couple a bridge compound to a donor. Another Z group that can used to link a bridge compound to a donor is
where Y
−
is a counter ion.
Other preferred bridge compounds of the invention have Formula II.
G is preferably —C═C—C═C—. X preferably is H or ═CH(—CH═CH)
d
—C(═O)H, where d is 0-3.
Other preferred bridge compounds of the invention have Formula III.
Preferably, J is CH
2
, O or S. Preferably, R
1
is —Q—C
n
H
2+1
, —Q—(CH
2
)
a
C
n
F
2n+1
, —Q—CH
2
SCH
2
C
n
F
2n+1
, or —Q—CH
2
SCH
2
CF
3
, where n is 1-10 and a is 0-10, or —Q—CH
2
OCH
2
CF
3
. Other halogens or deuterium can be used in place of F. Q preferably is either absent or, when present, O or S. X preferably has the formula (C═O)H, or C═CH(—CH═CH)
d
—C(═O)H, where d is 0-3. Z is a chemical group that is capable of being linked to a donor and includes, but is not limited to, —CH
2
—Br, —CH
2
—OH, —CH
3
, —C(═O)H, Br, I, and the like. Those skilled in the art can use additional groups known to those skilled in the art to couple a bridge compound to a donor. Another Z group that can be used to link a bridge compound to a donor is
where Y
−
is a counter ion.
The present invention is also directed to compounds which can serve as electro-optic chromophore donor-bridge compounds for use in, for example, thin polymer films for waveguides.
Preferred donor-bridge compounds of the invention have Formula IV.
Preferably, K is O or S. D is preferably an electron donating group. Preferably, R
1
is —Q—C
n
H
2+1
, —Q—(CH
2
)
a
C
n
F
2n+1
, —Q—CH
2
SCH
2
C
n
F
2n+1
, or —Q—CH
2
SCH
2
CF
3
, where n is 1-10 and a is 0-10, or —Q—CH
2
OCH
2
CF
3
. Other halogens or deuterium can be used in place of F. Q preferably is either absent or, when present, O or S. X preferably has the formula H or (—CH═CH)
b
—C(═O)H, where b is 0-3. Preferably, q is 1, 2, or 3.
Other preferred donor-bridge compounds of the invention have Formula V.
Preferably, R
1
is H, —Q—CH
2+1
, —Q—(CH
2
)
a
C
n
F
2n+1
, —Q—CH
2
SCH
2
C
n
F
2n+1
, or —Q—CH
2
SCH
2
CF
3
, where n is 1-10 and a is 0-10, or —Q—CH
2
OCH
2
CF
3
. Other halogens or deuterium can be used in place of F. Q preferably is either absent or, when present, O or S. D is preferably an electron donating group. X preferably has the formula (═O), or ═CH(—CH═CH)
d
—C(═O)H, where d is 0-3. R
2
and R
3
each, independently, are preferably C
n
H
2n+1
where n is 2-10.
Other preferred donor-bridge compounds of the invention have Formula VI.
Preferably, J is CH
2
, O or S. Preferably, R
1
is —Q—C
n
H
2n+1
, —Q—(CH
2
)
a
C
n
F
2n+1
, —Q—CH
2
SCH
2
C
n
F
2n+1
, or —Q—CH
2
SCH
2
CF
3
, where n is 1-10 and a is 0-10, or —Q—CH
2
OCH
2
CF
3
. Other halogens or deuterium can be used in place of F. Q preferably is either absent or, when present, O or S. D is preferably an electron donating group. X preferably has the formula (C═O)H, or C═CH(—CH═CH)
d
—C(═O)H, where d is 0-3.
DESCRIPTION OF PREFERRED EMBODIMENTS OF THE INVENTION
The present invention relates, in part, to novel electro-optic chromophore bridge compounds and donor-bridge compounds which have utility in organic nonlinear optical applications. Electro-optic chromophores comprising the donor-bridge compounds of the invention exhibit thermal stability to temperatures from 260° C. to 310° C. Chromophores comprising the donor-bridge compounds of the invention also show great solubility in most common organic solvents and, thus, are useful in most polymer films for waveguides. In addition, under intense UV-irradiation (365 nm, dosage 3 J/cm
2
up to 13 minutes), the chromophores comprising the donor-bridge compounds of the invention show no changes of UV-VIS-NIR spectrum, which indicates that the chromophores are, to a major extent, photo stable.
The compounds of the invention can be used in, for example, polymeric organic materials for optical waveguides. Such polymeric organic materials are described in, for example, U.S. Pat. Nos. 5,044,725, 4,795,664, 5,247,042, 5,196,509, 4,810,338, 4,936,645, 4,767,169, 5,326,661, 5,187,234, 5,170,461, 5,133,037, 5,106,211, and 5,006,285, each of which is incorporated herein by reference in its entirety.
The phrase “electron donating group” is used synonymously with “electron donator” and refers to substituents which contribute electron density to the &pgr;-electron system when the conjugated electron structure is polarized by the input of electromagnetic energy.
The phrase “donor-bridge compound” refers to an electron
He Mingqian
Leslie Thomas M.
Corning Incorporated
Douglas Walter M.
Moore Margaret G.
Peng Kuo-Liang
Rogalskyj Peter
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