Stock material or miscellaneous articles – Composite – Of inorganic material
Reexamination Certificate
1999-10-20
2002-03-26
Kelly, Cynthia H. (Department: 1774)
Stock material or miscellaneous articles
Composite
Of inorganic material
C428S917000, C428S704000, C313S504000, C313S506000
Reexamination Certificate
active
06361887
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to electroluminescent (EL) devices. More specifically, naphthylanthracene-based polymers used as luminescent materials in polymer EL devices.
BACKGROUND OF THE INVENTION
Electroluminescent devices are opto-electronic devices where light emission is produced in response to an electrical current through the device. The physical model for EL is the radiative recombination of electrons and holes. The term light emitting diode (LED) is commonly used to describe an EL device where the current-voltage behavior is non-linear, meaning that the current through the EL device is dependent on the polarity of the voltage applied to the EL device. Both organic and inorganic materials have been used for the fabrication of LEDs. Inorganic materials such as ZnS/Sn, Ga/Bs, Ga/As have been used in semiconductor lasers, small area displays, LED lamps, etc. However, the drawbacks of inorganic materials include difficulties to process and to obtain large surface areas and efficient blue light.
Organic polymers used as light-emitting materials in EL devices offer several advantages over inorganic materials, such as simpler manufacturing, low operating voltages, the possibility of producing large area and full-color displays. Conjugated polymers such as poly(phenylvinylene) (PPV) were first introduced as EL materials by Burroughes et al in 1990 (Burroughes, J. H.
Nature
1990, 347, 539-41). Considerable progress has been made since then to improve the stability, efficiency, and durability of polymeric LEDs (Sheats, J. R. et al
Science
1996, 273, 884-888; Berggren, M. et al
Nature
1994, 372, 444-6; Holmes, A. B. et al WO 94/29883 (1994); and Spreitzer, et al,
Adv. Mater.
1998, 10(16), 1340). Polymers with wide energy bandgap to emit blue light are important materials because stable, efficient blue-light-emitting materials with high brightness are desirable for full color EL display applications. With these primary materials, it is possible to produce other colors by a downhill energy transfer process. For instance, a green or red EL emission can be obtained by doping a blue EL host material with a small amount of green or red luminescent material.
Incorporating non-conjugated spacer groups into a conjugated polymer backbone is an effective approach to break conjugation thus increasing energy bandgap in order to emit blue light. These spacer groups usually prevent the extended conjugation and contribute to the solubility and film-forming properties of the polymer. Blue-light-emitting PPV (Aguiar, M et al
Macromolecules
1995, 28, 4598-602), polythiophene (Andersson, M. R. et al
Macromolecules
1995, 28, 7525-9), and PPP (Hilberer, A et al
Macromolecules
1995, 28, 4525-9) have been prepared by this approach. However, such spacer group can act as a barrier to the injection and mobility of the charge carriers which leads to high threshold voltages and operating voltages. Thus, it is desirable to develop processable new blue-light-emitting polymers with low driving voltages for full color display.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide wide energy bandgap luminescent polymeric materials useful for polymer EL devices.
It is a further object of the present invention to provide wide energy bandgap luminescent polymers which emit blue light.
These objects are achieved in an electroluminescent device comprises an anode, a cathode, and polymer luminescent materials disposed between the anode and cathode, the polymeric luminescent materials includes 9,10-di-(2-naphthyl)anthracene-based polymers of formula (I).
wherein:
R, R
1
, R
2
, R
3
, and R
4
are each individually hydrogen, or alkyl, or alkoxy of from 1 to 24 carbon atoms; aryl or substituted aryl of from 6 to 28 carbon atoms; or heteroaryl or substituted heteroaryl of from 4 to 40 carbons; or F, Cl, or Br; or a cyano group; or a nitro group;
X is a linking group; and
Y includes one or more comonomer units that are a substituted or unsubstituted alkyl, alkenyl, aryl, or heteroaryl or a conjugated group.
The present invention provides polymeric luminescent materials with a number of advantages which include good solubility and better thermal stability. With the primary wide energy bandgap chromophore, 9,10-di-(2-naphthyl)anthracene, other color emitting luminescent copolymers can be easily designed and produced by introducing the narrow energy bandgap chromorphores into the polymeric chain.
REFERENCES:
patent: 4356429 (1982-10-01), Tang
patent: 4769292 (1988-09-01), Tang et al.
patent: 5429884 (1995-07-01), Namiki et al.
patent: 5770070 (1998-07-01), Inbasekaran et al.
patent: 5776622 (1998-07-01), Hung et al.
patent: 5935721 (1999-08-01), Shi et al.
patent: 94/29883 (1994-12-01), None
Burroughes et al, Light-emitting diodes based on conjugated polymers, Nature, vo. 347, Oct. 11, 1990, pp. 539-541.
Sheats et al, Organic Electroluminescent Devices, Science, vol. 273, Aug. 16, 1996, pp. 884-888.
Berggren et al, Light-emitting diodes with variable colours from polymer blends, Nature, vol. 372, Dec. 1, 1994, pp. 444-446.
Aguiar et al, Light-Emitting Polymers with Pendant Chromophoric Groups, Macromolecules 1995, 28, pp. 4598-4602, No date.
Andersson et al, Electroluminescence from Substituted Poly(thiophenes): From Blue to Near Infrared, Macromolecules 1995, 28, pp. 7525-7529, No date.
Hilberger et al, Synthesis and Characterization of a New Efficient Blue-Light-Emitting Copolymer, Macromolecules 1995, 28, pp. 4525-4529, No date.
Miyaura et al, Palladium-Catalyzed Cross-Coupling Reactions of Organoboron Compounds, Chem. Rev. 95, 1995, pp. 2457-2483, No date.
Miyaura et al, The Palladium-Catalyzed Cross-Coupling Reaction of Phenylboronic Acid with Haloarenes in the Presence of Bases, Synthetic Communications, 11(7), 1981, pp. 513-519, No date.
Ranger et al, New Well-Defined Poly(2,7-fluorene) Derivatives: Photoluminescence and Base Doping, Macromolecules, 1997, 30, pp. 7686-7691, No date.
Kim et al, Water-Soluble Photo- and Electroluminescent Alkoxy-Sulfonated Poly(p-phenylenes) Synthesized via Palladium Catalysis, Macromolecules, 1998, 31, pp. 964-974, No date.
Ng et al, Quinoxaline-based conjugated polymers containing ruthenium (II) bipyridine metal complex, Macromol. Rapid Commun, 18, 1997, pp. 1009-1016, No date.
Shi Jianmin
Zheng Shiying
Eastman Kodak Company
Kelly Cynthia H.
Owens Raymond L.
Xu Ling
LandOfFree
Electroluminescent devices having naphthylanthracene-based... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Electroluminescent devices having naphthylanthracene-based..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Electroluminescent devices having naphthylanthracene-based... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2857945