Electric lamp and discharge devices – With luminescent solid or liquid material – Solid-state type
Reexamination Certificate
2000-09-29
2003-04-29
Dawson, Robert (Department: 1712)
Electric lamp and discharge devices
With luminescent solid or liquid material
Solid-state type
C313S504000, C428S917000, C252S301160, C252S301210, C252S301260, C252S301310, C430S073000, C430S074000, C564S305000, C564S306000, C564S426000, C564S431000, C564S434000, C564S442000, C564S453000, C564S457000, C564S458000, C564S461000, C564S511000
Reexamination Certificate
active
06555959
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a compound suitable for use for a filter dye, a color conversion filter, a dye for a photographic material, a sensitizing dye, a dye for pulp-dyeing, a laser dye, a fluorescent medicine for a medical diagnosis, a material for a light emitting device (luminescence device), etc., and particularly relates to a light emitting device using thereof.
BACKGROUND OF THE INVENTION
Prospects of an organic light emitting device in which organic materials are used are promising as a solid light emitting (luminescent) type inexpensive and large area full color display device and development has been tried variously. An organic light emitting device in general comprises a light emitting (luminescent) layer and a pair of counter electrodes with the light emitting layer between. When an electric field is impressed between both electrodes, electrons are injected from the cathode and positive holes are injected from the anode, and the electrons and the positive holes are recombined in the light emitting layer. A phenomenon of emitting energy as light when energy level is returned from conduction band to valence band is luminescence.
Organic light emitting devices so far been used require high driving voltage and emission luminance and luminous efficacy are low, but an organic EL device comprising lamination of thin layers containing an organic compound having high fluorescent quantum efficiency capable of emitting light with low voltage of 10 V or lower has been reported (
Applied Physics Letters
, Vol. 51, p. 913 (1987)) and attracting public attention in recent years. According to this technique, high luminance green light emission can be obtained by using a metal chelate complex as the electron-transporting layer, a fluorescent compound as the light emitting layer and an amine compound as the positive hole-transporting layer. Further, when taking into consideration the utilization of an organic light emitting device as a full color display and a light source, it is necessary to get three primary colors or a white color in practical use. A device capable of emitting a desired color by doping a fluorescent dye is reported (
Journal of Applied Physics
, Vol. 65, p. 3610 (1989)). This technique is particularly effective for red emission dyes in which extinction due to concentration is large and the emission of high efficacy is difficult when a fluorescent dye is used alone as the light emitting layer, and high color purity and high luminance have been attained due to the technique. However, when a device doped with a dye is produced by deposition, the operation is complicated and the performance of the device is liable to become uneven because a host material and a trace amount of a fluorescent dye are co-deposited. Therefore, from the viewpoint of the simplification of the producing step and the stability of the performance of a device, the development of light emitting materials of from orange to red capable of high luminance emission and excellent in durability even when a dye is used alone as the light emitting layer has so far been desired.
On the other hand, organic EL devices which have realized high luminance emission are laminated devices formed by vacuum deposition of organic materials, but from the viewpoint of simplification of producing step, process-ability, and realization of large area devices, it is desired to produce devices by a coating system. However, devices produced by a coating system so far been used are inferior to devices produced by a deposition system in the points of emission luminance and luminous efficacy, therefore, the realizations of high luminance and high efficacy luminescence have been left as the problems to be solved. In addition, with devices produced by coating an organic low molecular weight compound dispersed in an organic polymer medium, uniform planar emission for a long period of time is difficult due to the agglomeration of the organic low molecular weight compound.
Further, in recent years, various materials having fluorescence have been used for a filter dye, a color conversion filter, a dye for a photographic material, a sensitizing dye, a dye for pulp-dyeing, a laser dye, a fluorescent medicine for a medical diagnosis, a material for an organic light emitting device, etc., and demand for such materials has been increased. However, fluorescent dyes having high fluorescent strength and capable of long wave emission of from orange to red are less, therefore, the development of a novel material has been desired.
SUMMARY OF THE INVENTION
A first object of the present invention is to provide a material for a light emitting device of orange to red emission capable of emitting light with high luminance and high efficacy, excellent in stability at repeated use, and capable of uniform and planar emission with low voltage driving, and a light emitting device using the same.
A second object of the present invention is to provide a light emitting device showing no unevenness among devices and stable in performance, and a material capable of producing a light emitting device of red emission.
A third object of the present invention is to provide a material for a light emitting device capable of emitting light with high luminance and high efficacy even when a device is produced by coating system, and a light emitting device using the same.
A fourth object of the present invention is to provide a compound having fluorescence of from orange to red with high fluorescent strength.
The above objects of the present invention have been accomplished by the following means.
(1) A material for a light emitting device which is a compound represented by the following formula (I):
wherein Ar
1
and Ar
6
, which may be the same or different, each represents a divalent aryl group or a divalent heterocyclic group; R
2
, R
3
, R
7
and R
8
, which may be the same or different, each represents an aryl group, a heterocyclic group or an aliphatic hydrocarbon group; R
4a
, R
5a
, R
9a
and R
10a
, which may be the same or different, each represents a hydrogen atom or a monovalent group, and at least one of R
4a
, R
5a
, R
9a
and R
10a
represents an electron withdrawing group having a Hammett's &sgr;
p
value of 0.2 or more; at least two of Ar
1
, R
2
, R
3
, R
4a
, and R
5a
may be linked to form a ring; at least two of R
9a
, R
10a
, Ar
6
, R
7
, and R
8
may be linked to form a ring; at least two of R
4a
, R
5a
, R
9a
and R
10a
may be linked to form a ring; L
1
represents (i) a divalent monocyclic or bicyclic aryl group, or a divalent monocyclic or bicyclic aryl group to which a heterocyclic ring is condensed, (ii) a divalent heterocyclic group, or (iii) a divalent group comprising two divalent aryl groups, two divalent heterocyclic groups, or a divalent aryl group and a divalent heterocyclic group, which groups are each connected by a single bond, a vinyl group, a C═X group, a silyl group, an aryl group, a 6-membered aromatic heterocyclic group, a 5-membered aromatic heterocyclic group having a carbon atom, a nitrogen atom and an oxygen atom as the ring-constitutional atoms, or the combination of these groups; L
1
and at least one of R
4a
and R
5a
may be linked to form a ring; L
1
and at least one of R
9a
and R
10a
may be linked to form a ring; X represents an oxygen atom, a sulfur atom, N—R
x1
or CR
x2
R
x3
; and R
x1
, R
x2
and R
x3
, which may be the same or different, each represents a hydrogen atom or a substituent.
(2) The material for a light emitting device as described in the above item (1), wherein the compound represented by formula (I) is a compound represented by the following formula (II):
wherein Ar
1
, Ar
6
and L
1
each has the same meaning as in formula (I); Ar
2
, Ar
3
, Ar
7
and Ar
8
, which may be the same or different, each represents an aryl group or a heterocyclic group; R
4b
, R
5b
, R
9b
and R
10b
, which may be the same or different, each represents a hydrogen atom, a heterocyclic group, a perhalogenoalkyl group, a cyano group, an oxycarbonyl group, a carbamoyl group,
Dawson Robert
Robertson Jeffrey B.
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