Stock material or miscellaneous articles – Composite – Of inorganic material
Reexamination Certificate
1999-12-29
2002-06-04
Kelly, Cynthia H. (Department: 1774)
Stock material or miscellaneous articles
Composite
Of inorganic material
C428S690000, C428S917000, C428S704000, C313S504000, C313S506000, C252S301160
Reexamination Certificate
active
06399223
ABSTRACT:
TECHNICAL FIELD This invention relates to an organic electro luminescent (EL) device, and more particularly, to a compound for use in a device of the type wherein an electric field is applied across a thin film of an organic compound to emit light.
BACKGROUND TECHNIQUE
Organic electroluminescent (EL) devices include a thin film containing a luminescent organic compound interleaved between an electron injecting electrode and a hole injecting electrode. Electrons and holes are injected into the thin film where they are recombined to create excitons. Light is emitted by utilizing luminescence (phosphorescence or fluorescence) upon deactivation of excitons.
The organic EL devices are characterized by plane light emission at a high luminance of about 100 to 10,000 cd/m
2
with a voltage of about 10 volts and light emission in a spectrum from blue to red color by a simple choice of the type of fluorescent material.
Doping is one technique for producing light emission of any desired color from EL devices. It was reported in Jpn. J. Appl. Phys., 10, 527 (1971) to change emission color from blue to green by doping anthracene crystals with a minor level of tetracene. With respect to organic thin film EL devices having a multilayer structure, it was reported in JP-A 63-264692 to incorporate in a host reported in JP-A 63-264692 to incorporate in a host material having a light emitting function a minor amount of a fluorescent dye capable of emitting light different from that of the host material in response to light emission from the host material as a dopant to form a light emitting layer, thereby changing the color of light emission from green to orange or red.
With respect to long wavelength light emission of yellow to red, known light emitting materials or dopant materials include laser dyes capable of red oscillation (EP 0281381), compounds capable of exciplex emission (JP-A 2-255788), perylene compounds (JP-A 3-791), coumarin compounds (JP-A 3-792), dicyanomethylene compounds (JP-A 3-162481), thioxanthene compounds (JP-A 3-177486), mixtures of a conjugated polymer and an electron transporting compound (JP-A 6-73374), squalirium compounds (JP-A 6-93257), oxadiazole compounds (JP-A 6-136359), oxynate derivatives (JP-A 6-145146), and pyrene compounds (JP-A 6-240246).
Other light emitting materials disclosed heretofore include condensed polycyclic aromatic compounds (JP-A 5-32966 and 5-214334). Also dopant materials proposed heretofore include various condensed polycyclic aromatic compounds (JP-A 5-258859).
These light emitting systems, however, do not provide high luminance or stable light emitting performance, especially at long wavelength. A further improvement in luminance or durability is thus desired.
DISCLOSURE OF THE INVENTION
An object of the invention is to provide a compound for use in an organic EL device and an organic EL device which produce light emission of satisfactory luminance, especially at long wavelength and are durable in that improved light emitting performance lasts for a long time.
This and other objects of the invention are attained by the following construction.
(1) A compound for organic electroluminescent devices, having a basic skeleton represented by the following formula (I):
(CF 3)
wherein R
1
to R
8
each are hydrogen or a substituted or unsubstituted aryl or alkenyl group, with the proviso that at least six of R
1
to R
8
are substituted or unsubstituted aryl or alkenyl groups.
(2) An organic electroluminescent device comprising a hole injecting electrode, an electron injecting electrode, and an organic layer disposed between the electrodes and including at least a light emitting layer, wherein
said light emitting layer contains the compound of (1).
(3) The organic electroluminescent device of (2), wherein the compound contained in said light emitting layer has a basic skeleton represented by the following formula (II):
(CF 4)
wherein each R group in sets of R
11
to R
15
, R
21
to R
25
, R
31
to R
35
, and R
41
to R
45
is hydrogen or a substituted or unsubstituted alkyl, aryl, amino, heterocyclic or phenoxy group, the R groups in at least two sets have substituted or unsubstituted aryl, heterocyclic or aryloxy groups as substituents; R
5
, R
6
, R
7
and R
8
each are hydrogen or an aryl group, with the proviso that at least two of R
5
to R
8
are aryl groups; at least two R groups in each of the sets of R
11
to R
15
, R
21
to R
25
, R
31
to R
35
, and R
41
to R
45
may form a fused ring.
(4) The organic electroluminescent device of (2) or (3) wherein said light emitting layer further contains an electron injecting and transporting compound and/or a hole injecting and transporting compound.
(5) The organic electroluminescent device of any one of (2) to (4) wherein said light emitting layer contains at least two compounds.
(6) The organic electroluminescent device of any one of (2) to (5) wherein said light emitting layer contains at least two dopants, the content of the dopants combined being up to 30% by weight based on a host material.
(7) The organic electroluminescent device of any one of (2) to (6) wherein the overall content of the compound of (1) in said light emitting layer is up to 30% by weight based on a host material.
(8) The organic electroluminescent device of (6) or (7) wherein said light emitting layer contains at least two compounds having different carrier trapping capabilities.
(9) The organic electroluminescent device of (7) or (8) wherein said light emitting layer contains at least a compound having a hole trapping capability and a compound having an electron trapping capability.
(10) The organic electroluminescent device of any one of (1) to (9) wherein at least two light emitting layers are included, and said light emitting layers contain dopants having different carrier trapping capabilities.
(11) The organic electroluminescent device of any one of (1) to (10) wherein at least two light emitting layers are included, at least one layer of said light emitting layers contains a dopant having a hole trapping capability, and at least one other layer of said light emitting layers contains a dopant having an electron trapping capability.
REFERENCES:
patent: 61-85487 (1986-05-01), None
patent: 4-335087 (1992-11-01), None
patent: 6-167807 (1994-06-01), None
patent: 7-65958 (1995-03-01), None
patent: 8-231951 (1996-09-01), None
patent: 10-114890 (1998-05-01), None
patent: 10-289786 (1998-10-01), None
Jeffrey A. Dodge, et al., J. Org. Chem., vol. 55, No. 13, pp. 4190-4198, “Regioselective Synthesis of Substituted Rubrenes”, 1990.
Aotani Junji
Fujita Tetsuji
Inoue Tetsushi
Kelly Cynthia H.
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
TDK Corporation
Xu Ling
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