Specific silane compounds, method of synthesizing them,...

Details Specific silane compounds, method of synthesizing them,... Specific silane compounds, method of synthesizing them,...

2000-04-04

2001-10-23

Shaver, Paul F. (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Silicon containing

C556S430000, C556S431000, C428S690000, C428S212000, C428S917000, C313S504000, C313S506000, C549S006000, C549S214000, C548S110000, C544S229000, C546S014000

Reexamination Certificate

active

06307083

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to silane compounds, a method of synthesizing them, luminescent device materials comprising silane compounds, and luminescent devices containing such materials.
BACKGROUND OF THE INVENTION
Nowadays various types of display devices using organic fluorescent materials (organic luminescent devices) are actively researched and developed. Of these devices, much attention is focused on organic electroluminescent (EL) devices. This is because organic EL devices are promising display devices capable of emitting light of high luminance under a low applied voltage. For instance, the EL devices of a type which comprises organic thin layers formed by evaporating organic compounds are known (
Applied Physics Letters
, vol. 51, p. 913 (1987)). More specifically, the organic EL devices of such a type have a laminated structure made up of an electron transfer material and a hole transfer material, and their luminous characteristics show substantial improvements over those of conventional devices of single-layer type.
With the reports printed in the journal described above, the study and development of organic EL devices have been made energetically. And developments of electron transfer materials and hole transfer materials have been attempted with the intention of enhancing luminous efficiency. As to the development of electron transfer materials, however, no compounds superior in properties to tris(8-hydroxyquinolinato)aluminum (usually abbreviated as “Alq”) have yet been found. Such being the case, it has been desired to develop compounds capable of surpassing Alq in properties. In addition, Alq fluoresces a green color, so that it has no suitability as an electron transfer material for blue luminescent devices Therefore, it has been desired to find out electron transfer materials suitable for blue luminescent devices.
Also, the application of organic EL devices to full color display has been lively examined in recent years. In order to develop a high-performance full color display, it is necessary to heighten the color purity of each of blue luminescence, green luminescence and red luminescence. However, the luminescence of high color purity is difficult to obtain. For instance, the distyrylarylene compounds (DPVBi) described in a book, entitled
Yuki EL Soshi to sono Kogyoka Saizensen
(which means “Organic EL devices and the forefront of their industialization”), page 38, published by N.T.S. Co., and Zn(OXZ)
2
(benzene ring-condensed nitrogen-containing heterocyclic compounds) described in the book, supra, page 40, and JP-A-7-133483 (the term “JP-A” as used herein means an “unexamined published Japanese patent application”) are blue luminescent materials which have undergone extensive examinations, but they can merely provide blue luminescence of low color purity. Therefore, there is plenty of room for improvement.
Another important characteristic that is required for organic EL device materials is durability. In particular, the amorphous film stability constitutes an important factor in the enhancement of durability. Therefore, it has been expected to develop compounds usable as organic EL device materials and capable of forming highly stable amorphous films. For instance, N,N′-diphenyl-N,N′-di(m-tolyl)benzidine (TPD) is an extensively utilized hole transfer material and has high hole transfer capacity. Although the TPD evaporated film can be in a uniform amorphous state for a short while after the evaporation was finished, cases occurs in which the evaporated film crystallizes after a lapse of several hours. In such cases, the durability of EL devices is greatly lowered.
SUMMARY OF THE INVENTION
Objects of the present invention are to develop an organic luminescent device material which can ensure high luminous efficiency and high durability in the organic luminescent device, and to provide a luminescent device comprising such a material.
The aforementioned objects are attained in accordance with the following Embodiments (1) to (4).
(1) A compound represented by the following formula (1):
wherein each of R
1
and R
2
groups represents an aryl group containing no alkenyl substituent or a heteroaryl group containing no alkenyl substituent; each of R
3
, R
4
, R
5
and R
6
groups represents a hydrogen atom or a substituent group; each of R
7
and R
8
groups represents an aryl group or a heteroaryl group; and each of Ar
1
and Ar
2
groups represents an arylene group or a heteroarylene group; provided that the compound represented by the formula (1) takes neither polymeric nor oligomeric form and the case is excluded therefrom wherein all or three of R
1
, R
2
, Ar
1
and Ar
2
groups have heteroaryl structures.
(2) A luminescent device material, comprising a compound represented by the formula (1) defined in Embodiment (1).
(3) A luminescent device, containing at least one compound represented by the formula (1) defined in Embodiment (1).
(4) A method of synthesizing a compound represented by the formula (1) defined in Embodiment (1), comprising a step of reacting an alkenyl compound with the halide or trifluoromethanesulfonate derivative in the presence of a palladium catalyst to form the C—C bond.
DETAILED DESCRIPTION OF THE INVENTION
The compounds represented by formula (1) of the present invention are described below in detail.
R
1
and R
2
each represents an aryl group having no alkenyl substituent (containing preferably 6 to 30, more preferably 6 to 20, particularly preferably 6 to 12, carbon atoms, with examples including phenyl, p-methylphenyl and naphthyl groups) or a heteroaryl group having no alkenyl substituent (containing preferably 1 to 50, more preferably 1 to 30, particularly preferably 2 to 12, carbon atoms in addition to any of oxygen, sulfur and nitrogen atoms, with examples including imidazolyl, pyridyl, furyl, thienyl, piperidyl, benzoxazolyl and triazolyl groups). The aryl or heteroaryl group represented by R
1
and R
2
each may be substituted by any of the substituent groups represented by R
3
, which are described below, as long as an alkenyl group is excluded therefrom.
It is desirable for R
1
and R
2
each to be an unsubstituted aryl group or an unsubstituted heteroaryl group, further preferably an unsubstituted aryl group, particularly preferably an unsubstituted phenyl group.
Each of R
3
, R
4
, R
5
and R
6
groups represents a hydrogen atom or a substituent group. Examples of such a substituent group include an alkyl group (containing preferably 1 to 30, more preferably 1 to 12, further preferably 1 to 6, carbon atoms, with examples including methyl, t-butyl and hexyl groups), an alkenyl group (containing preferably 2 to 30, more preferably 2 to 12, further preferably 2 to 6, carbon atoms, such as a propenyl group), an alkynyl group (containing preferably 2 to 30, more preferably 2 to 12, further preferably 2 to 6, carbon atoms, such as an ethynyl group), an aryl group (containing preferably 6 to 40, more preferably 6 to 20, further preferably 6 to 12, carbon atoms, with examples including phenyl, naphthyl and anthryl groups), a heteroaryl group (containing preferably 1 to 40, more preferably 2 to 20, further preferably 3 to 12, carbon atoms in addition to any of oxygen, sulfur and nitrogen atoms, with examples including pyridyl, thienyl and carbazolyl groups), an alkoxy group (containing preferably 1 to 30, more preferably 1 to 12, further preferably 1 to 6, carbon atoms, such as a methoxy group or an isopropoxy group), an aryloxy group (containing preferably 6 to 40, more preferably 6 to 20, further preferably 6 to 12, carbon atoms, with examples including phenoxy, naphthoxy and pyrenyloxy groups), a halogen atom (such as chlorine, bromine or fluorine atom), an aliphatic heterocyclic group (containing preferably 1 to 40, more preferably 2 to 20, further preferably 3 to 12, carbon atoms in addition to any of oxygen, sulfur and nitrogen atoms, such as s piperidyl group or a morpholino group), and a cyano group. These substituent groups each may further have a substituent group.
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