Stock material or miscellaneous articles – Composite – Of inorganic material
Reexamination Certificate
2001-04-10
2003-10-07
Kelly, Cynthia H. (Department: 1774)
Stock material or miscellaneous articles
Composite
Of inorganic material
C428S917000, C313S504000, C313S506000, C257S040000, C257S103000, C252S301350
Reexamination Certificate
active
06630254
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to the field of optics, and more particularly Organic Light Emitting Diodes (OLEDs).
2. Description of the Related Art
Organic materials show promise for electronic and opto-electronic applications. Low-cost of synthesis, processing and room temperature fabrication are among the economical advantages. OLEDs are of particular promise for displays as they can be tuned to any color, organic diodes are very efficient and the visual properties of the diodes are excellent. Liquid crystal displays are currently overwhelmingly dominating the laptop computer market, but the technology has limitations such as low efficiency, poor vision angle, and speed and temperature range limitations.
It has long been felt that a technically viable emissive display technology could compete with LCDs, and OLEDs are today considered in the best position to do just that. OLEDs are also of great interest for other markets, such as lighting.
Intense research is going on at the chemistry laboratory level to find materials with high luminous quantum efficiency, good color purity and stability for the application to OLED displays. While some materials meet or exceed some of the requirements for commercial displays, none meets them all. Tang and VanSlyke, from Eastman Kodak, discovered small molecules that yield very efficient and stable green diodes [U.S. Pat. No. 4,356,429, Oct. 26, 1982; C. W. Tang and S. A. VanSlyke, Appl. Phys. Lett. 51, 913 (1987)].
FIG. 1
shows a typical OLED diode as described by Tang and VanSlyke: it is composed of TPD (a triphenyl diamine derivative), a hole transport layer, and AlQ
3
(a chelated Aluminum hydroxyquinoline), an electron transport and emitter layer.
When a sufficiently high positive voltage is applied between the anode and cathode, holes are injected in the hole transport layer from an anode, electrons are injected in the electron transport layer from a cathode. Holes and electrons recombine at the interface between the two organic materials and create an exciton that will release energy as light or heat. Light is emitted through the anode, which can be Indium Tin Oxide, a transparent degenerate semiconductor with a relatively high work function that favors hole injection. The cathode is usually a low work function metal like Ca, Mg or Al. TPD and AlQ
3
are now commercially available. However, blue and red emitters in the same class of materials usually have shorter lifetimes and lower luminous efficiencies.
The glass transition temperature of small molecules is usually quite low (as low as 60° C. for TPD), so displays made of small molecules have difficulty meeting some of the temperature requirements. On the contrary, polymers usually have high glass transition temperatures. It is also desirable to find a family of materials that will emit in the three primary colors to permit the creation of full-color displays: this is easier with polymers than small molecules. Finally, small molecules have to be evaporated to form thin films, whereas polymers can be easily soluble and can be spun-on or reel-coated. This means that polymers are potentially lower cost to process and easier to coat on large surface for large display applications.
Conjugated polymers are considered a very important class of electroactive and photoactive materials because they possess a highly delocalized pi-electron system, and transport charges efficiently [Heeger, McDiarmid and Shirakawa, 2000 Nobel Prize, http://www.nobelprizes.com/]. Scientists from Cambridge University, UK, discovered that PPVs (poly(p-phenyenevinylene)s) can be a very efficient green emitter [U.S. Pat. No. 5,247,190, priority date Apr. 20, 1989; J. H. Burroughes et al, Nature, v347,539 (1990)].
FIG. 2
shows a typical diode as described by Burroughes et al. A 70 nm PPV is sandwiched between an ITO conductive transparent layer and an aluminum cathode. The thin PPV layer transports electrons, holes and is also the green emitter. When a sufficiently high positive voltage is applied between the anode and cathode, holes injected from the anode and electrons injected from the cathode recombine radiatively to produce green light. Many other compounds have been studied since and incorporated in diodes producing all colors [see for review R. H. Friend et al, Nature, v397, 121 (1999)]. Green, however, is still the only color with sufficient lifetime, so there is still the need for a family of polymers that will emit in all colors of the spectrum, and optimize their use in OLEDs.
SUMMARY OF THE INVENTION
According to the present invention there is provided an Organic Light Emitting Diode (OLED) comprising as its active material a conjugated poly(N-alkyl-2,7-carbazole) derivative described by the formula:
wherein n is an integer of about 3 to about 100, and R represents a substituant that is a linear or branched alkyl group containing 1 to 22 carbon atoms, or poly(ethyleneoxy), cyano, aryl, amide or benzoyl.
Polycarbazoles are a well-known class of polymers. Two of the present inventors have discovered how to synthesise highly conjugated poly(N-alkyl-2,7-carbazole) and have filed a patent application entitled “Conjugated Polycarbazole Derivatives and Process for the Synthesis thereof” on their method of synthesis, the contents of which are incorporated herein by reference. In the present invention the conjugated polycarbazole derivatives are used as the active material in OLEDs either alone or mixed with another material.
Carbazole monomers can also be alternated with other monomers to form copolymers according to the general formula:
Where Z is any type of comonomer, x is an integer between 1 and 100, y is an integer between 0 and 100, and n is an integer of about 3 to about 100.
The conjugated polycarbazole derivatives comprise repeating or alternating units of the above formula. For example, the comonomers can be selected from ethylene, acetylene, C
6
-C
22
mononuclear/polynuclear aromatic, C
2
-C
10
mononuclear/polynuclear heterocyclic groups and tertiary arylamines. Examples of mononuclear/polynuclear aromatic groups are: fluorene, anthracene, phenylene, naphthylene, acenaphthene, phenanthrene, fluoranthene, pyrene, perylene, rubrene, chrysene, tetracene and pentacene.
Examples of mononuclear/polynuclear heterocyclic internal groups include 5-member heterocycles such as furan, thiophene, pyrrole, oxazole, isooxazole, oxadiazoles, thiazole, isothiazole, imidazole, thiadiazole, and pyrazoles; 6-member heterocycles such as pyridine, pyridazine, pyrimidine, pyrazine, triazines, and tetrazenes; benzo-fused ring systems such as benzoxazole, benzothiazole, benzimidazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, phthalazine, benzothiadiazole, and benzotriazines; polynuclear fused condensed ring systems such as phenazine, phenanthridine, acridine, and diphenylene oxide. Examples of tertiary arylamine groups include triphenylamine, N,N′-diphenylbenzidine, N,N′-diphenyl-1,4-phenylenediamine, and diphenylnaphthylamine. Olefinic, arylamino, aromatic and heterocyclic aromatic groups containing up to 30 carbons are useful for the present purpose. They may be substituted optionally with one or more substituents. Examples of substituents include C
1
-C
20
hydrocarbyl radicals, C
1
-C
20
(thio)alkoxy radicals, C
1
-C
20
(thio)aryloxy radicals, cyano, fluoro, chloro, C
1
-C
20
alkoxycarbonyl, C
1
-C
20
aryoxylcarbonyl, poly(alkyleneoxy) and alkyl(aryl)sulfonyl radicals. Such substituents may be selected to improve the solubility or processing characteristics of the polymer. In such cases, the substituent is preferably selected from alkyl alkoxy, poly(alkyleneoxy), and cyano.
OLEDs can consist of many different layers with different roles. They are sandwiched between two electrodes, metallic or semiconductive, to provide injection of electrodes and holes. There is a layer between those two electrodes where recombination of those charges takes place and produces the emission of light. Th
D'Iorio Marie
Leclerc Mario
Levesque Isabelle
Morin Jean-Francois
Py Christophe
(Marks & Clerk)
Garrett Dawn
Kelly Cynthia H.
National Research Council of Canada
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