Stock material or miscellaneous articles – Composite – Of inorganic material
Reexamination Certificate
2000-02-15
2002-03-19
Kelly, Cynthia H. (Department: 1774)
Stock material or miscellaneous articles
Composite
Of inorganic material
C428S704000, C428S917000, C252S301160, C252S301260, C252S301310, C313S504000, C313S506000, C546S113000, C546S118000
Reexamination Certificate
active
06358634
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a novel nitrogen-containing heterocyclic compound, an organic light-emitting device material comprising such a nitrogen-containing heterocyclic compound and an organic light-emitting device containing such a nitrogen-containing heterocyclic compound.
BACKGROUND OF THE INVENTION
Today, various display devices comprising organic fluorescent materials are under extensive study. Among these display devices, organic EL (electroluminescence) devices can emit light having a high luminance even when driven at a low voltage and thus are noted as favorable display device. For example, an EL device comprising an organic thin film layer formed by evaporation of an organic compound has been known (as disclosed in
Applied Physics Letters
, vol. 51, page 913, 1987). The organic EL device disclosed in the above cited reference has a laminated structure comprising an electron-transporting material and a positive hole-transporting material and thus exhibits drastically improved light-emitting properties as compared with the conventional single-layer devices.
With this report as a turning-point, organic EL devices have been under extensive research and development. Accordingly, the development of electron-transporting materials and hole-transporting materials providing an enhanced light-emitting efficiency have been extensively studied. However, no compounds superior to Alq(Tris(8-hydroxyquinolinato)aluminum) have been found yet in the development of electron-transporting materials. It has thus been desired to provide improved electron-transporting materials. Further, Alq fluoresces green and thus is not appropriate as an electron-transporting material for blue light-emitting device. This, too, is why the development of improved electron-transporting materials has been desired.
Moreover, the application of organic EL devices to full-color display has been recently studied extensively. In order to develop a high performance full-color display, it is necessary to enhance the purity of the colors, i.e., blue, green and red, of light emitted. However, it is difficult to emit light having a high color purity. For example, benzo-condensed nitrogen-containing heterocyclic compounds as disclosed in Seizo Miyata, Organic EL devices and its forefront of industrialization, NTS, page 40, 1998, JP-A-7-133483 (The term “JP-A” as used herein means an “unexamined published Japanese patent application”), and JP-A-10-330744 are widely studied blue light-emitting materials but can emit only a blue light having a low color purity. It has thus been desired to provide organic EL devices having an improved color purity.
SUMMARY OF THE INVENTION
It is therefore an object of the present invention to provide an organic light-emitting device material such as electron-transporting material and light-emitting material capable of emitting light having a high luminance and a high color purity.
The foregoing object of the present invention will become apparent from the following detailed description and examples.
The foregoing object of the present invention is accomplished by the following aspects of the present invention:
(1) An organic light-emitting device material comprising a compound having a partial structure represented by the following general formula (I):
wherein R
11
and R
12
each represent a hydrogen atom or a substituent, with the proviso that R
11
and R
12
are not bonded to form a benzo condensed ring; X
1
represents an oxygen atom, a sulfur atom, a substituted or unsubstituted nitrogen atom or —C(R
13
)R
14
—; R
13
and R
14
each represent a hydrogen atom or a substituent; Y
1
represents an oxygen atom, a sulfur atom or a substituted or unsubstituted nitrogen atom; M
1
represents a metal ion or a hydrogen atom; and Z
1
represents an atomic group required to form a 5- or 6-membered ring.
(2) An organic light-emitting device material comprising a compound having a partial structure represented by the following general formula (II):
wherein Q
1
represents an atomic group required to form a heterocyclic group; X
2
represents an oxygen atom, a sulfur atom, a substituted or unsubstituted nitrogen atom or —C(R
15
)R
16
—; R
15
and R
16
each represent a hydrogen atom or a substituent; Y
2
represents an oxygen atom, a sulfur atom or a substituted or unsubstituted nitrogen atom; M
2
represents a metal ion or a hydrogen atom; and Z
2
represents an atomic group required to form a 5- or 6-membered ring.
(3) A compound represented by the following general formula (III):
wherein R
21
and R
22
each represent a hydrogen atom, an alkyl group, an aryl group or a heteroaryl group; X
3
represents an oxygen atom, a sulfur atom, a substituted or unsubstituted nitrogen atom or —C(R
23
)R
24
—; R
23
and R
24
each represent a hydrogen atom or a substituent; Y
3
represents an oxygen atom, a sulfur atom or a substituted or unsubstituted nitrogen atom; M
3
represents a metal ion; q
1
represents an integer of not less than 1; L
1
represents a ligand; me represents an integer of not less than 0; and Z
3
represents an atomic group required to form a 5- or 6-membered ring.
(4) A compound represented by the following general formula (IV):
wherein Q
2
represents an atomic group required to form a heterocyclic group; X
3
represents an oxygen atom, a sulfur atom, a substituted or unsubstituted nitrogen atom or —C(R
25
)R
26
—; R
25
and R
26
each represent a hydrogen atom or a substituent; Y
4
represents an oxygen atom, a sulfur atom or a substituted or unsubstituted nitrogen atom; M
4
represents a metal ion; q
2
represents an integer of not less than 1; L
2
represents a ligand; m
2
represents an integer of not less than 0; and Z
4
represents an atomic group required to form a 5- or 6-membered ring.
(5) An organic light-emitting device comprising a pair of electrodes having a light-emitting layer or a plurality of organic thin film layers containing said light-emitting layer formed interposed therebetween, wherein at least one of said plurality of organic thin film layers comprises at least one of compounds defined in the foregoing aspects (1) to (4) of the present invention incorporated therein.
(6) The organic light-emitting device according to the aspect (5), wherein at least one of said plurality of organic thin film layers is formed by a coating process.
DETAILED DESCRIPTION OF THE INVENTION
The foregoing compound of the present invention is a compound having a partial structure represented by the general formula (I). The compound having a partial structure represented by the general formula (I) is preferably a metallic complex. Such a metallic complex may be a compound having at least one partial structure represented by the general formula (I) incorporated therein. The metallic complex may also be a so-called polynuclear complex having a plurality of metal specifies per molecule. Further, the metallic complex may have a plurality of ligands. More preferably, the compound of the present invention is a neutral metallic complex.
The general formula (I) will be further described hereinafter.
R
11
and R
12
each represent a hydrogen atom or a substituent. Examples of the substituent represented by R
11
or R
12
include an alkyl group (preferably C
1-20
(wherein “C
1-20
”, means 1 to 20 carbon atoms, hereinafter the same), more preferably C
1-12
, particularly C
1-8
alkyl group such as methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl and cyclohexyl), an alkenyl group (preferably C
2-20
, more preferably C
2-12
, particularly C
2-8
alkenyl group such as vinyl, allyl, 2-butenyl and 3-pentenyl), an alkinyl group (preferably C
2-20
, more preferably C
2-12
, particularly C
2-8
alkinyl group such as propargyl and 3-pentinyl), an aryl group (preferably C
6-30
, more preferably C
6-20
, particularly C
6-12
aryl group such as phenyl, p-methylphenyl and naphthyl), a substituted carbonyl group (preferably C
1-20
, more preferably C
1-16
, particularly C
1-12
substituted carbonyl group such as acetyl, benzoy
Igarashi Tatsuya
Okada Hisashi
Fuji Photo Film Co. , Ltd.
Kelly Cynthia H.
Sughrue & Mion, PLLC
Xu Ling
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