Stock material or miscellaneous articles – Composite – Of inorganic material
Reexamination Certificate
1999-10-12
2002-09-03
Yamnitzky, Marie (Department: 1774)
Stock material or miscellaneous articles
Composite
Of inorganic material
C428S917000, C313S504000, C313S506000
Reexamination Certificate
active
06444333
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a material for a luminescent (organic luminescent) device capable of converting electric energy into light and emitting light and also relates to a luminescent device using the material. The luminescent device can be suitably used in the fields of display device, display, back light, electrophotography, illumination light source, recording light source, reading light source, marking, billboard, interior decoration and the like.
The present invention also relates to a tetraarylmethane compound useful as a charge transporting agent for use in organic electroluminescent (EL) devices and electrophotographic photoreceptors.
2. Description of the Related Art
At the present time, developments and studies on various display devices are being aggressively made. In particular, organic electroluminescent (EL) devices can obtain highly bright luminescence at a low voltage and accordingly, are drawing an attention as a promising display device.
VanSlyke, Tang et al. reveal, for example, in U.S. Pat. Nos. 4,539,507 and 4,720,432, and JP-A-5-234681 (the term “JP-A” as used herein means an “unexamined published Japanese patent application”) that when an aromatic tertiary amine containing a phenyl group, a phenylene group or a biphenylene group is used in the electron (hole) injecting and transporting zone of an internal connection organic electroluminescent (EL) device, the light output stability is improved and the operating life is prolonged. Thereafter, improvements of aromatic tertiary amine are studied by many researchers with an attempt to attain further stability of the light output, and reported in a large number of patent applications and scientific literatures. For example, biphenyl-base tertiary amines are reported in
Japanese Journal of Applied Physics
, 27, L269 (1988), JP-A-59-194393
, Appl. Phys. Lett
., 66, 2679 (1995), JP-A-5-234681, JP-A-7-331238, JP-A-8-48656 and WO95/09147, and star burst tertiary amines are reported in
Appl. Phys. Lett
., 65, 807 (1994), and JP-B-7-110940 (the term “JP-B” as used herein means an “examined Japanese patent publication”). However, the compounds heretofore disclosed are not satisfied in the performance (particularly, storage stability) and still in need of improvements.
Among organic EL devices, devices obtained by laminating organic substance layer through vacuum evaporation make a success in realizing light emission with high luminance. However, in view of simplification of the production process, workability and the like or for obtaining a large area, the device is preferably fabricated by a coating method. The devices fabricated by the conventional coating method are, however, inferior in the luminance of light emitted and the luminescent (quantum) efficiency as compared with the devices fabricated by the deposition method. Thus, improvements are still in need for attaining light emission with high luminance and high efficiency.
In recent years, the practical use of electrophotographic photoreceptor (organic photoconductor (OPC)) has been spreading rapidly, and the OPC completely plays a central role of electrophotographic photoreceptors. Most of recent OPCs are laminate type OPCs comprising a charge generating material (CGM) and a charge transfer material (CTM). Due to electrophotographic photoreceptors of laminate type OPC, sensitivity to visual light, charge retaining properties, surface strength, etc., are greatly improved. While hydrazone compounds (JP-B-55-42380, JP-A-57-101844, JP-A-54-150128, etc.), triarylamine compounds (JP-B-58-32372, etc.) and stilbene compounds (JP-A-58-198043, etc.) are used as CTM, the devices using these CTM compounds in the related art are inferior in properties (e.g., sensitivity) for recent speeding up. Accordingly, improvements are still in need. The study on CTM has been extensively carried out, and novel hydrazone compounds (JP-A-8-143550), carbazole type stilbene compounds (JP-A-8-59615) and tri-substituted ethylene compounds (JP-A-63-225660, JP-A-9-59256) are proposed recently. However, improvements are still in need.
SUMMARY OF THE INVENTION
An object of the present invention is to provide a material for an organic luminescent device capable of driving at low voltage, emitting light with high luminance and high efficiency, and exhibiting excellent stability on repeated use, and to provide an organic luminescent device using the material.
Another object of the present invention is to provide i a novel compound for use in organic electroluminescent (EL) and electrophotoraphic photoreceptors.
A further object of the present invention is to provide a novel charge transporting agent for use in organic electroluminescent (EL) devices and electrophotoraphic photoreceptors, which can exhibit excellent charge transporting ability or storage stability.
The above-described objects can be attained by the following means:
(1) an organic luminescent device material which is a compound represented by the following formula (I):
Formula (I)
wherein V, W, X and Y each represents L
1
—NR
1
R
2
, wherein R
1
and R
2
each represents an aliphatic hydrocarbon group, an aryl group or a heterocyclic group, R
1
and R
2
may be combined directly or indirectly to form a ring, and L
1
represents a divalent linking group containing an aryl group and/or an aromatic heterocyclic group;
(2) an organic luminescent device material which is a compound represented by the following formula (II):
Formula (II)
wherein Ar
21
and Ar
22
each represents an aryl group, Ar
21
and Ar
22
may be combined to each other directly or indirectly to form a ring, and L
2
represents a divalent linking group containing an aryl group and/or an aromatic heterocyclic group;
(3) an organic luminescent device material which is a compound represented by the following formula (III):
Formula (III)
wherein Ar
31
and Ar
32
each represents an aryl group, Ar
31
and Ar
32
may be combined to each other directly or indirectly to form a ring, and L
3
represents an arylene group;
(4) an organic luminescent device material which is a compound represented by the following formula (IV):
Formula (IV)
wherein Ar
41
and Ar
42
each represents an aryl group, Ar
41
and Ar
42
may be combined to each other directly or indirectly to form a ring, n represents an integer of from 1 to 4, R represents a substituent, and m represents an integer of from 0 to 4;
(5) an organic luminescent device comprising a pair of electrodes having formed therebetween a light emitting layer or a plurality of organic compound thin films including a light emitting layer, wherein at least one layer contains the organic luminescent device material described in (1) to (4) above;
(6) an organic luminescent device comprising a pair of electrodes having formed therebetween a light emitting layer or a plurality of organic compound thin films including a light emitting layer, wherein at least one layer comprises a polymer having dispersed therein the organic luminescent device material described in (1) to (4) above; and
(7) a novel tetraarylmethane compound represented by the following formula (V):
Formula (V)
wherein Ar
1
and Ar
2
, which may be the same or different, each represents an aryl group which may be substituted, Ar
1
and Ar
2
may be combined directly or indirectly through a linking group, R represents a halogen atom, an alkyl group which may be substituted, an aryl group which may be substituted, an alkoxy group which may be substituted, an aryloxy group which may be substituted, a dialkylamino group which may be substituted, an N-alkyl-N-arylamino group which may be substituted or a diarylamino group which may be substituted, when a plurality of Rs are present, Rs may be the same or different, m represents an integer of from 0 to 4, and n represents an integer of from 1 to 4.
DETAILED DESCRIPTION OF THE INVENTION
The compound represented by formula (I) is described in detail below.
V, W, X and Y, which may be the same or different, each represents L
1
—NR
1
R
2
, wherein R
1
and R
2
ea
Asanuma Naoki
Okada Hisashi
Sato Tadahisa
Fuji Photo Film Co. , Ltd.
Sughrue & Mion, PLLC
Yamnitzky Marie
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