Compositions – Organic luminescent material containing compositions – Scintillating or lasing compositions
Reexamination Certificate
2000-12-15
2002-10-08
Dentz, Bernard (Department: 1625)
Compositions
Organic luminescent material containing compositions
Scintillating or lasing compositions
C546S112000, C546S094000
Reexamination Certificate
active
06461538
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a novel indolizine compound, a method for producing a novel indolizine compound, an organic light-emitting device material having an indolizine skeleton, and an organic light-emitting device using these.
BACKGROUND OF THE INVENTION
At present, studies on and development of various display elements are aggressively proceeding. In particular, organic EL light-emitting devices can afford high luminance emission at a low voltage and is attracting 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 emission properties as compared with conventional single-layer devices.
As concerns the hole-transporting material used in the laminate-type device, triarylamine derivatives including TPD (N,N′-di-m-tolyl-N,N′-diphenylbezidine), and &pgr;-electron excess aromatic compounds such as pyrrole, carbazole and thiophene, are known as excellent hole-transporting materials. These &pgr;-electron excess aromatic compounds are acknowledged to be effective not only as a hole-transporting material but also as an electron-transporting material, a hole-injecting material or a light-emitting material. However, these compounds have high crystallinity and the organic light-emitting devices using such a compound are known to have a problem in that the device performance is liable to greatly deteriorate during storage, particularly storage at a high temperature.
Triarylamine derivatives are low in the solubility in an organic solvent and these compounds are not suitable for coating-type organic EL devices.
As an electron-transporting material capable of taking the place of the triarylamine derivatives, use of a nitrogen-containing heterocyclic compound such as carbazole derivative is being studied and a large number of cases have been reported on the technique of using a low molecular carbazole derivative or a polyvinyl carbazole as the hole-transporting material, for example, a compound described in
Oyo Butsuri Gakkai Yuki Bunshi Bioelectronics Bunka
-
kai, Dai
6-
kai Koshu
-
kai Yoko
(1997) (
Society of Applied Physics, Section of Organic Molecules Bioelectronics,
6
th Lecture, Preprint
), or the like.
However, as a result of investigations by the present inventors on the compounds such as carbazole derivative, these compounds have a high potential of ionization and have a problem in that an organic EL device capable of emitting light with high efficiency cannot be obtained.
As means for solving the problem of deterioration of the device performance during storage, techniques of, in the case of triarylamine derivatives, introducing a condensed polycyclic aromatic group or using a group of compounds improved in the symmetry property are disclosed in
Appl. Phys. Lett.,
56, 799 (1990),
Polymer Preprints
(
ACS
), 349 (1997), and the like. Similarly, investigations on nitrogen-containing heterocyclic compounds such as carbazole derivative, and techniques of increasing the molecular weight are disclosed in
Appl. Phys. Lett.,
63, 2627 (1993).
The present inventors had found that indolizine compounds are effective as the organic light-emitting device material and continuously studied on these compounds. Then, it was found that the indolizine compounds have a problem, similarly to the heterocyclic compounds in series, in that when a compound having a simple structure is used in the organic light-emitting material, a sufficiently high performance cannot be obtained.
Furthermore, in the case of using a known Chichibabin method for synthesizing the indolizine compound, it was difficult to introduce a substituent into various positions of the indolizine mother nucleus. Particularly, in introducing a substituent into the 5-position of the indolizine mother nucleus, when the substituent was introduced into a pyridine ring of the starting material, the synthesis of indolizine mother nucleus encountered great steric hindrance and the mother nucleus was difficult to form. When the substituent was attempted to introduce after the ring formation, the substituent could not be easily introduced into the 5-position because the 1-position and 3-position of the indolizine mother nucleus were extremely high in the reactivity with an electrophilic reacting agent.
In recent years, examples of the metalation reaction at the 5-position of the indolizine mother nucleus are reported in
Tetrahedron Lett.,
33 (31), 4433-4434 (1992). The present inventors thought that by utilizing this reaction, a substituent may be introduced into the 5-position of the indolizine mother nucleus, and made extensive investigations, as a result, it has been found that an indolizine boronic acid ester is effective.
The present invention has been accomplished as a result of these extensive investigations.
SUMMARY OF THE INVENTION
A first object of the present invention is to develop a heterocyclic compound having a good hole-transporting ability and thereby develop an EL device material suitable for the manufacture of high-luminance organic EL device.
A second object of the present invention is to develop a hole-transporting material capable of exhibiting good film-forming property at the fabrication of a device and imparting high stock storability to the device and in turn develop an EL device material having excellent stock storability.
A third object of the present invention is to develop an EL device material suitable for the manufacture of an organic EL device capable of emitting high-luminance light even in the case of a coating-type device.
A fourth object of the present invention is develop a novel indolizine compound and thereby developing an organic light-emitting material suitable for the manufacture of an organic light-emitting device having high luminance and excellent durability.
A fifth object of the present invention is to find out a novel indolizine compound and a production process therefore and develop an organic light-emitting material suitable for the manufacture of a high-luminance organic light-emitting device.
These objects of the present invention can be attained the following indolizine compound, production process therefor, organic light-emitting device material and organic light-emitting device.
1) An organic light-emitting device material comprising at least one compound represented by formula (I) or a precursor thereof:
wherein R
1
to R
7
each independently represents hydrogen atom, a halogen atom, a cyano group, a formyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted primary amino group, a substituted or unsubstituted secondary amino group, a substituted or unsubstituted tertiary amino group, a substituted or unsubstituted imino group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted alkylthio group, a substituted or unsubstituted arylthio group, a substituted or unsubstituted carbonamido group, a substituted or unsubstituted sulfonamido group, a substituted or unsubstituted carbamoyl group, a substituted or unsubstituted sulfamoyl group, a substituted or unsubstituted alkylcarbonyl group, a substituted or unsubstituted arylcarbonyl group, a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted arylsulfonyl group, a substituted or unsubstituted alkoxycarbonyl group, a substituted or unsubstituted aryloxycarbonyl group, a substituted or unsubstituted alkylcarbonyloxy group, a substituted or unsubstituted arylcarbonyloxy group, a substituted or unsubstituted urethane group, a substituted or unsub
Burns Doane , Swecker, Mathis LLP
Dentz Bernard
Fuji Photo Film Co. , Ltd.
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