Stock material or miscellaneous articles – Composite – Of inorganic material
Reexamination Certificate
2002-01-10
2003-07-15
Yamnitzky, Marie (Department: 1774)
Stock material or miscellaneous articles
Composite
Of inorganic material
C428S917000, C313S504000, C313S506000
Reexamination Certificate
active
06593013
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a cyclic azine dye and an electroluminescence (EL) device using the same.
BACKGROUND OF THE INVENTION
At the present time, development and study on various display devices are aggressively driven. In particular, organic EL devices can obtain high luminance light emission at a low voltage and accordingly, are drawing an attention as a promising display device. For example, an EL device comprising an organic thin film formed by depositing an organic compound is known (see,
Applied Physics Letters
, Vol. 51, page 913 (1987)). The organic EL device described in this publication has a laminate structure comprising an electron transporting material and a hole transporting material and is greatly improved in the light emission properties as compared with conventional single-layer devices.
As a means to improve the light emission efficiency of the laminate-type EL device, a method of doping a fluorescent dye is known. For example, an organic EL device having doped therein a coumarin dye described in
Journal of Applied Physics
, Vol. 65, page 3,610 (1989) is greatly improved in the light emission efficiency as compared with non-doped devices.
Furthermore, by doping a fluorescent dye, light having a desired wavelength can be taken out. In order to apply the organic EL device to a full color display or back light, a fluorescent dye capable of emitting light at an appropriate wavelength and having excellent durability must be developed, in particular, a red fluorescent dye is being demanded in view of durability and light emission efficiency.
As the red fluorescent dye used in the organic electroluminescence device, 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyrane (DCM), for example, is doped and thereby emission of red orange light is obtained, however, this dye has problems that the color purity is low and the durability is poor, and cannot be used in practice. Neil Red is also known, however, this is still disadvantageous in that the color hue is short wave and the durability is not sufficiently high. In the same way, various EL devices which can emit light at a longer wavelength than the green light as a result of doping a fluorescent material have been developed, however, these devices all have serious problems that the color purity is low as red color light emission and the luminance of emitted light is not sufficiently high. EL devices using a conventional red fluorescent dye have another problem that the durability is low. Furthermore, with respect to a fluorescent dye which emits light in the blue green area, dyes capable of emitting light with excellent luminance and having superior durability have not yet been developed and a new dye is being demanded.
Of organic EL devices, devices in which an organic material is laminated by vacuum deposition can successfully achieve high luminance light emission, 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 emitted light and the light emission efficiency to the devices fabricated by the deposition method. Thus, improvements are still in need for attaining high luminance and highly efficient light emission.
SUMMARY OF THE INVENTION
A first object of the present invention is to provide an organic EL device using a red fluorescent dye capable of emitting red light in high color purity and having excellent durability.
A second object of the present invention is to provide a red fluorescent dye which can be used in an organic EL device, emits red light in high color purity and has excellent durability.
A third object of the present invention is to provide an organic EL device which can ensure high luminance and highly efficient light emission even when the device is fabricated by a coating method.
A fourth object of the present invention is to provide an organic EL device using a fluorescent dye capable of emitting light in the blue green area and having excellent durability.
The present invention provides the following electroluminescence devices and fluorescent dyes and thereby the above-described objects of the present invention can be attained.
[1] An organic electroluminescence device comprising at least one organic thin film between electrodes, which contains at least one compound represented by the following formula (1), (2) or (3):
wherein X
11
represents an oxygen atom, a sulfur atom or N—R
19
, and R
11
to R
18
and R
19
, which may be the same or different, each represents a hydrogen atom or a substituent, provided that R
16
and R
17
are not combined to form an aromatic ring;
wherein X
21
represents an oxygen atom, a sulfur atom or N—R
2b
, Y
21
represents an oxygen atom or a sulfur atom, and R
21
to R
29
and R
2b
, which may be the same or different, each represents a hydrogen atom or a substituent, and R
2a
represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, an unsubstituted amino group, an acylamino group, a sulfonyl-amino group, a carbamoylamino group, a sulfamoylamino group, an alkoxycarbonylamino group, an aryloxycarbonylamino group, a phosphoramido group, an acyl group, a carbamoyl group, a sulfonyl group, a sulfamoyl group, a cyano group or a halogen atom, provided that when X
21
represents an oxygen atom and R
29
represents a hydrogen atom, at least one of R
26
to R
29
represents an unsubstituted or substituted amino group;
wherein X
31
, represents an oxygen atom, a sulfur atom or N—R
3b
, Z
31
, represents NR
31
R
32
or OG
31
, R
31
to R
36
and R
3b
each represents a hydrogen atom or a substituent, and G
31
represents a hydrogen atom, a substituent or a counter cation group.
[2] A cyclic azine compound having a structure represented by the following formula (4):
wherein X
41
represents an oxygen atom, a sulfur atom or N—R
4b
, R
4b
represents a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a substituted carbonyl group having from 1 to 20 carbon atoms or a substituted sulfonyl group having from 0 to 20 carbon atoms, R
4
, and R
42
each represents a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms or an aryl group having from 6 to 20 carbon atoms, R
43
, R
44
and R
45
each represents a hydrogen atom, a substituted or unsubstituted alkyl group having from 1 to 20 carbon atoms, a halogen atom, a hydroxy group, a substituted or unsubstituted alkoxy group having from 1 to 20 carbon atoms, an unsubstituted amino group, a substituted amino group having from 1 to 20 carbon atoms, the substituted amino group being an alkylamino group, an arylamino group, a sulfonamido group, a carbonamido group, a ureido group, a urethane group, a carbamoylamino group or a sulfamoylamino group, R
46
, R
47
, R
48
and R
49
each represents a hydrogen atom, a halogen atom, a substituted carbonyl group having from 1 to 30 carbon atoms, an alkylamino group having from 1 to 30 carbon atoms, an arylamino group having from 6 to 30 carbon atoms a sulfonylamino group having from 1 to 30 carbon atoms, an acylamino group having from 2 to 30 carbon atoms, a ureido group having from 1 to 30 carbon atoms, an alkoxycarbonylamino group having from 2 to 30 carbon atoms, an aryloxycarbonylamino group having from 7 to 30 carbon atoms, a carbamoylamino group having from 1 to 30 carbon atoms or a sulfamoylamino group having from 1 to 30 carbon atoms, and R
4a
represents a hydrogen atom, a cyano group, a substituted carbonyl group having from 1 to 30 carbon atoms, a sulfamoyl group having from 0 to 30 carbon atoms, a sulfonyl group having from 1 to 30 carbon atoms, a sulfonamido group having from 1 to 30 carbon atoms, a carbonamido group having from 1 to 30 carbon atoms or a ureido group having from 1 to 30 carbon atoms, provided that when X
41
is an oxygen atom and R
4a
, represents a hyd
Igarashi Tatsuya
Nii Kazumi
Fuji Photo Film Co. , Ltd.
Sughrue & Mion, PLLC
Yamnitzky Marie
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