Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Reexamination Certificate
2000-04-05
2001-10-30
Shaver, Paul F. (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
C556S430000, C556S431000, C556S467000, C556S004000, C556S467000, C556S467000, C556S014000, C556S467000, C556S110000, C556S467000, C556S467000, C556S428000, C556S467000, C556S467000, C556S467000, C313S504000, C313S506000
Reexamination Certificate
active
06310231
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to particular silane compounds, luminescent device materials comprising such compounds, and luminescent devices containing such materials. BACKGROUND OF THE INVENTION
Nowadays various display devices (organic luminescent devices) utilizing organic fluorescent materials are researched and developed energetically. Of these devices, the organic electroluminescent (EL) devices are promising display devices that deserve special attention because they can emit 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, such a type of organic EL devices 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 cited above, the study and development of organic EL devices have been made lively. And various electron transfer materials and hole transfer materials have been developed and examined for the purpose of enhancing luminous efficiency. As to the 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 actively 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 present in a uniform amorphous state for a short while after the evaporation was finished, cases occurs in which the TPD evaporated film crystallizes after a lapse of several hours have passed from the evaporation. In such cases, the durability of EL devices is greatly lowered.
SUMMARY OF THE INVENTION
An object of the present invention is to develop an organic luminescent device material which can ensure high luminous efficiency and high durability in the luminescent device, and to provide a luminescent device using such a material.
The aforementioned object is attained in accordance with the following Embodiments (1) to (9).
(1) A luminescent device material, with the material comprising a compound represented by the following formula (1)
wherein R
1
represents an alkyl group, an aryl group, a heteroaryl group or an alkynyl group, and each of Ar
11
, Ar
12
and Ar
13
represents a heteroaryl group.
(2) A luminescent device material, with the material comprising a compound represented by the following formula (2):
wherein R
2
represents an alkyl group, an aryl group, a heteroaryl group or an alkynyl group, each of Ar
21
, Ar
22
and Ar
23
represents an arylene group, and each of R
21
, R
22
and R
23
represents an aryl group or a heteroaryl group.
(3) A luminescent device material, with the material comprising a compound represented by the following formula (3)
wherein R
3
represents an alkyl group, an aryl group, a heteroaryl group or an alkynyl group, each of Ar
31
, Ar
32
and Ar
33
represents an arylene group, and each of R
31
, R
32
and R
33
represents an alkenyl group or an alkynyl group.
(4) A luminescent device material, with the material comprising a compound represented by the following formula (4):
wherei n R
4
represents an alkyl group, an aryl group, a heteroaryl group or an alkynyl group, each of Ar
41
Ar
42
and Ar
43
represents an arylene group, each of R
41
, R
42
and R
43
represents —NR
44
R
45
, —OR
46
or —S—R
47
, and each of R
44
, R
45
, R
46
and R
47
represents a hydrogen atom or a substituent group.
(5) A luminescent device material, with the material comprising a compound represented by the following formula (5)
wherein R
5
represents an alkyl group, an aryl group, a heteroaryl group or an alkynyl group, and each of Ar
51
, Ar
52
and Ar
53
represents a group containing at least three aromatic hydrocarbon rings in a condensed state.
(6) A compound represented by the following formula (6):
wherein each of R
61
and R
62
represents a substituent group, l
1
represents an integer of 0 to 4, and l
2
represents an integer of 0 to 12.
(7) A compound representedby the following formula (7):
wherein R
71
represents a substituent group, and l
1
represents an integer of 0 to 9.
(8) A compound represented by the following formula (8)
wherein each of R
81
and R
82
represents a substituent group, l
4
represents an integer of 0 to 4, and i
5
represents an integer of 0 to 8.
(9) A luminescent device containing at least one among the compounds represented by the formulae (1), (2), (3), (4), (5), (6), (7) and (8) defined in Embodiments (1), (2), (3), (4) (5), (6), (7) and (8) respectively.
DETAILED DESCRIPTION OF THE INVENTION
The compounds of the present invention (namely the compounds represented by formulae (1), (2), (3), (4), (5), (6), (7) and (8) respectively) are described below in detail.
First, the groups constituting the formula (1) are illustrated.
R
1
represents an alkyl group (containing preferably 1 to 20, more preferably 1 to 12, particularly preferably 1 to 8, carbon atoms, with examples including methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl and cyclohexyl groups), an aryl group (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), a heteroaryl group (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, piperidyl, benzoxazolyl, thienyl, triazolyl and carbazolyl groups), or an alkynyl group (containing preferably 2 to 20, more preferably 2 to 12, particularly preferably 2 to 8, carbon atoms, with examples including propargyl and 2-pentynyl groups). These groups may further be substituted.
It is desirable for R
1
to be an alkyl group, an aryl group or a heteroaryl group, more preferably an aryl group or a heteroaryl group, further preferably a heteroaryl group, particularly preferably —Ar
14
group (wherein Ar
14
has the same meaning as A
11
described below).
Ar
11
, Ar
1
Igarashi Tatsuya
Taguchi Toshiki
Fuji Photo Film Co. , Ltd.
Shaver Paul F.
Sughrue Mion Zinn Macpeak & Seas, PLLC
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