Active solid-state devices (e.g. – transistors – solid-state diode – Organic semiconductor material
Reexamination Certificate
2002-12-04
2004-03-30
Crane, Sara (Department: 2811)
Active solid-state devices (e.g., transistors, solid-state diode
Organic semiconductor material
C257S103000, C313S506000, C428S917000
Reexamination Certificate
active
06713781
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to an organic light emitting device (OLED) in which a phenanthroline-fused phenazine or its derivative is used as an emissive layer, an electron transport layer, a hole-blocking layer, and/or a host material.
2. Description of the Related Art
OLEDs are commercially attractive for various display applications due to their high efficiency, low driving voltage, wide color range, light weight, simple device fabrication and potential low cost. Great efforts have been made to develop effective materials for use in these devices.
OLEDs typically comprise an emissive layer sandwiched between a transparent anode, such as transparent indium tin oxide (ITO), and a metal cathode, such as Mg, Al, Ag or their alloys. When a bias is applied across the electrodes, holes and electrons are respectively injected from the anode and cathode into the emissive layer, typically facilitated by hole transport and electron transport layers adjacent to the respective electrodes. The holes and electrons radiatively combine in the emissive layer and emit light.
In many cases, the doping of a functional material into a host material may lead to improved performance. Improved performance also may be achieved through the utilization of blocking layers, which block either holes or electrons from escaping the device.
Because of consumer expectations of good efficiency, long lifetime and pure color for OLEDs, a need exists for the development of effective materials for use in these devices.
SUMMARY OF THE INVENTION
It is an object of the invention to provide an improved OLED in which phenanthroline-fused phenazine or its derivative is used as an emissive layer, an electron transport layer, a hole-blocking layer, and/or a host material for a functional dopant.
Thus, in one aspect, the invention is an OLED in which an organic layer is sandwiched between an anode and a cathode, and in which the organic layer includes a phenanthroline-fused phenazine based compound.
In one embodiment of the invention, the phenanthroline-fused phenazine based compound is 1,10-phenanthroline-fused phenazine with the following structure:
wherein R
1
to R
8
independently represent H, an alkyl group, an alkoxy group, or an aromatic group.
In another embodiment of the invention, the phenanthroline-fused phenazine based compound is 1,7-phenanthroline-fused phenazine with the following structure:
wherein R
1
to R
8
independently represent H, an alkyl group, an alkoxy group, or an aromatic group.
In another embodiment of the invention, the phenanthroline-fused phenazine based compound is a 4,7-phenanthroline-fused phenazine with the following structure:
wherein R
1
to R
8
independently represent H, an alkyl group, an alkoxy group, or an aromatic group.
In another embodiment of the invention, the phenanthroline-fused phenazine based compound is 1,10-phenanthroline-fused phenazine of the following structure:
wherein R
1
to R
8
independently represent H, an alkyl group, an alkoxy group, or an aromatic group; X represents O, S, NR, with R being H or an alkyl group, CH
2
, CH
2
CH
2
, or a fused or substituted aromatic group; and n is an integer from 1 to 12, wherein X may not be present when n is 1.
In another embodiment of the invention, the phenanthroline-fused phenazine based compound is 1,7 phenanthroline of the following structure:
wherein R
1
to R
8
independently represent H, an alkyl group, an alkoxy group, or an aromatic group; X represents O, S, NR, with R being H or an alkyl group, CH
2
, CH
2
CH
2
, or a fused or substituted aromatic group; and n is an integer from 1 to 12, wherein X may not be present when n is 1.
In another embodiment of the invention, the phenanthroline-fused phenazine is 4,7-phenanthroline-fused phenazine with the following structure:
wherein R
1
to R
8
independently represent H, an alkyl group, an alkoxy group, or an aromatic group; X represents O, S, NR, with R being H or an alkyl group, CH2, CH2CH2, or a fused or substituted aromatic group; and n is an integer from 1 to 12, wherein X may not be present when n is 1.
Some preferred phenanthroline-fused phenazine based compounds are listed below:
wherein R
9
and R
10
independently are H, CH
3
or another alkyl group;
wherein X is O, S, NR, with R being H, CH
3
or another alkyl group, CH
2
or CH
2
CH
2
.
1,7 phenanthroline-fused phenazine or 4,7 phenanthroline-fused phenazine may be substituted for 1,10 phenanthroline-fused phenazine in the above-listed structures.
According to the invention, the phenanthroline-fused phenazine based compound can be used as an emissive layer, a hole blocking layer, and/or an electron transport layer. Further, the compound can be used as a host material for a functional guest material. The functional guest material may be an emitter, a hole-blocker, and/or an electron transporter.
The phenanthroline-fused phenazine based compound can be used in both electro-fluorescent and electro-phosphorescent OLEDs.
REFERENCES:
patent: 4772563 (1988-09-01), Evangelista et al.
patent: 5393614 (1995-02-01), Nakada
patent: 5645948 (1997-07-01), Shi et al.
patent: 5792567 (1998-08-01), Kido et al.
patent: 5904994 (1999-05-01), Dodabalapur et al.
patent: 6010796 (2000-01-01), Kijima
patent: 6013384 (2000-01-01), Kido et al.
patent: 6288229 (2001-09-01), Komatsuzaki et al.
patent: 6524728 (2003-02-01), Kijima et al.
patent: 2001-267080 (2001-09-01), None
patent: 00/70655 (2000-11-01), None
“Synthesis and Study of a Mixed-ligand Ruthenium(ii) Complex in Its Ground and Excited States”, Amouyal, et al., Journal Of The Chemical Society, Dalton Transactions, Inorganic Chemistry, (1990), No. 5, pp. 1841-1845.
“Mononuclear and Binuclear Tetrapyrido [3,2-a:2′,3′-c:3″,2″-h:2′′,3′″-j]phenazine (tpphz) Ruthenium and Osmium Complexes”, Bolger, et al., Inorganic Chemistry (1996), vol. 35, No. 10, pp 2937-2944.
“Stepwise Syntheses of Mono- and Di-nuclear Ruthenium tpphz Complexes”, Bolger, et al., Journal Of The Chemical Society, Chemical Communications (1995), No. 17, pp. 1799-1800.
“Superradiant properties of 4,4′-bis(1H-phenanthro[9,10-d]imidazol-2-yl)biphenyl and how a laser dye with exceptional stability can be obtained in only one synthetic step”, Krebs, et al., Tetrahedron Letters 42 (2001), pp. 6753-6757.
“Design and Application of Electron-Transporting Organic Materials”, Strukelj, et al., Science (1995), vol. 267, pp. 1969-1972.
“High electron mobility in bathophenanthroline”, Naka, et al., Applied Physics Letters (2000), vol. 76, No. 2, pp. 197-199.
“Introduction of Benzo[h]quinoline and 1, 10-Phenanthroline Subunits by Friedländer Methodology”, Riesgo, et al., Journal of Organic Chemistry (1996), vol. 61, No. 9, pp. 3017-3022.
Chen Jian Ping
Li Xiao-Chang Charles
Canon Kabushiki Kaisha
Crane Sara
Fitzpatrick ,Cella, Harper & Scinto
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