Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Nitrogen-containing reactant
Reexamination Certificate
2002-09-12
2004-12-21
Truong, Duc (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Nitrogen-containing reactant
C528S423000, C528S398000, C528S391000, C528S487000
Reexamination Certificate
active
06833432
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention pertains to improvements in the field of conjugated polymers. More particularly, the invention relates to conjugated poly(2,7-carbazole) derivatives and to a process for the preparation thereof.
A conjugated polymer is a polymer which possesses a delocalized pi-electron system along its backbone as described, for example, by D. J. Sandman in “Trends in Polymer Science”, Vol. 2, p. 44 (1994). Conjugated polymers are considered as a very important class of electroactive and photoactive materials by both academic and industrial laboratories. The synthesis over the last twenty years of highly pure polyacetylene, polythiophenes, polyphenylenes, polyfluorenes, ladder polymers and other conjugated polymers with optimized physical properties has led to a significant improvement in the performance of these polymeric materials and to a better understanding of their structure-property relationships. However, up to now, only poorly conjugated poly(N-alkyl-3,6-carbazole) derivatives are available so that these are not optimized for the development of light-emitting diodes, electrochromic windows, electrochemical sensors, photovoltaic cells, photoconductors, photorefractive materials, transistors, etc.
SUMMARY OF THE INVENTION
It is therefore an object of the present invention to provide conjugated poly(2,7-carbazole) derivatives having improved optical and electrochemical properties.
According to one aspect of the invention, there is provided a conjugated poly(N-alkyl-2,7-carbazole) of formula (I):
wherein R represents a linear or branched alkyl group having 1 to 22 carbon atoms, and n is an integer of about 3 to about 100.
The present invention also provides, in another aspect thereof, a process for preparing a conjugated poly(N-alkyl-2,7-carbazole) of the formula (I) defined above, which comprises treating a N-alkyl-2,7-difunctionnalized carbazole of formula (II):
wherein R is as defined above and X represents a trifluoromethanesulfonyl group or a halogen atom selected from the group consisting of bromine, chlorine and iodine atoms, with triphenylphosphine and 2,2′-bipyridine in the presence of zinc and nickel chloride, to cause polymerization of the compound of formula (II). A
According to a further aspect of the invention, there is provided a conjugated polymer comprising alternating or random units of formula (I′):
wherein R is as defined above.
The polymers comprising alternating units of formula (I′) can be obtained by Suzuki on Stille couplings. The polymers comprising random units of formula (I′), on the other hand, can be obtained by Yamamato-couplings.
The conjugated poly(2,7-carbazole) derivatives according to the invention, comprising repeating, alternating or random units of formula (I′), have interesting optical and electrochemical properties which render them suitable for use in the manufacture of light-emitting diodes, electrochromic windows, electrochemical sensors, photovoltaic cells, photoconductors, photorefractive materials and the like.
REFERENCES:
D.J. Sandman, Trends in Polymer Science (TRIP), 1994, vol. 2, No. 2, pp. 44-55.
Peter A.S. Smith et al., “The Reaction of Aryl Azides with Hydrogen Halides”, presented at the National Meeting of the American Chemical Society, San Francisco, Mar. 1949.
B.R. Hsieh et al., Macromolecules, 1985, vol. 18, pp. 1388-1394.
T. Yamamoto et al., Macromolecules, 1992, vol. 25, pp. 1214-1223.
M. Ranger et al., Macromolecules, 1997, vol. 30, pp. 7688-7691.
M. Murata et al., J. Org. Chem., 2000, vol. 65, pp. 164-168.
J.F. Morin et al., Macromolecules, 2001, vol. 34, pp. 4680-4682.
M. Leclerc, Journal of Polymer Science: Part A: Polymer Chemistry, 2001, vol. 39, pp. 2867-2873.
Geissler et al. “Polyarylenes on the Basis of Alkylpyrrole and Alkycarbazole Derivatives and their Oligomeric Model Systems.” Polymers for Advanced Technologies, vol. 8, pp. 87-92.
Schenk et al. “Novel Oligo(phenylenevinylenes): Models for the Charging of Extended &pgr; Chains.” J. Am. Chem. Soc. 1991, vol. 113, pp. 2634-2647.
Geissler et al. “Polyarylenes on the Basis of Alkylpryrrole and Alkylcarbazole Derivatives and their Oligomeric model Systems”. Abstract 126:212647.
Siove et al. “Thermal Transistions in Poly (N-alkyl-3,6-carbazolylenes).” Abstract 119:250891.
Faid et al. “Investigation of the Electrocatalyzed Step Polymerization of Soluble Electroactive Poly (N-alkyl-3,6-carbazolylenes).” Abstract 119:181323.
Siove et al. “Chain Length Effect on the Electroactivity of Poly (N-alkyl-3,6-carbazolediyl) Thin Films.” Abstract 114:31798.
Matsura et al. “Polymers of Carbazole Derivatives.” Abstract 111: 40172.
Meng et al. “Synthesis and Electrochemical Characterization of a New Polymer Constituted of Alternating Carbazole and Oxadiazole Moieties.” Abstract 131:88268.
Leclerc Mario
Morin Jean-Francois
Sidley Austin Brown & Wood LLP
Universite Laval
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