Stock material or miscellaneous articles – Composite – Of inorganic material
Reexamination Certificate
2001-01-08
2004-02-24
Yamnitzky, Marie (Department: 1774)
Stock material or miscellaneous articles
Composite
Of inorganic material
C428S917000, C313S504000, C313S506000, C564S308000, C564S426000, C564S427000
Reexamination Certificate
active
06696178
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to cyclocondensed polycyclic hydrocarbon compounds, light-emitting device materials which can convert electric energy to light to emit the light, and light-emitting devices. More particularly, the invention relates to light-emitting devices which can be suitably used in the fields of display devices, displays, backlights, electrophotography, illumination light sources, recording light sources, exposure light sources, reading light sources, markings, billboards, interior decorations and the like.
BACKGROUND OF THE INVENTION
At the present time, the research and development of various display devices have been actively made. In particular, organic light-emitting devices have attracted attention as promising display devices, because they can provide highly bright luminescence at low voltage. For example, a light-emitting device in which an organic thin film is formed by vapor deposition of an organic compound (
Applied Physics Letters,
51, 913 (1987)) has been known. The light-emitting device described in this literature is substantially improved in luminescence properties compared with conventional single-layer devices, by using tris(8-hydroxyquinolinato)aluminum complex (Alq) as an electron-transporting material and laminating a hole-transporting material (amine compound) therewith.
In recent years, the application of organic light-emitting devices to full color displays has been actively studied. However, for developing high performance full color displays, it is necessary to improve properties of each of blue, green and red light-emitting devices. For example, in regard to the blue light-emitting device, distyrylarylene compounds (DPVBi) described in “The Front Line of Organic EL Devices and Their Industrialization”, page 38 (supervised by Seizo Miyata, NTS Co. Ltd., 1998) have been widely studied. However, problems have arisen in terms of color purity, durability, luminescence luminance and efficiency, so that it has been desired that these problems should be solved.
Organic light-emitting devices realizing highly bright luminance are devices in which organic materials are applied by vapor deposition to form a laminate. The fabrication of the devices by coating is preferred from the viewpoints of simplification of manufacturing processes, processability and enlargement of their area. However, the devices fabricated by the conventional coating system, in particular, blue light-emitting devices are inferior in luminescence luminance and light-emission efficiency to the devices fabricated by vapor deposition. Accordingly, development of novel blue light-emitting device materials has been desired.
SUMMARY OF THE INVENITON
It is therefore an object of the invention is to provide light-emitting devices good in luminescence properties.
Another object of the invention is to provide light-emitting device materials good in luminescence properties.
The objects of the invention have been attained by the following:
(1) An organic light-emitting device comprising a light-emitting layer or a plurality of organic compound thin layers including a light-emitting layer formed between a pair of electrodes, wherein at least one layer comprises at least one kind of compound represented by the following formula (1):
wherein R
11
, R
12
and R
13
each represents a group having a cyclocondensed polycyclic hydrocarbon structure in which three or more rings are cyclocondensed;
(2) The organic light-emitting device described in the above (1), wherein the compound represented by the formula (1) is a compound represented by the following formula (2):
wherein Ar
11
, Ar
12
and Ar
13
each represents a group having an anthracene structure, a phenanthrene structure or a pyrene structure, R
21
, R
22
and R
23
each represents a substituent, and n
1
, n
2
and n
3
each represents an integer of from 0 to 4;
(3) The organic light-emitting device described in the above (2), wherein Ar
11
, Ar
12
and Ar
13
each represents an anthryl group, a phenanthryl group, a pyrenyl group, an anthrylphenyl group, a perylenyl group, a chrysenyl group, a triphenylenyl group or groups in which cyclocondensation is further conducted to these structures;
(4) The organic light-emitting device described in the above (2), wherein Ar
11
, Ar
12
and Ar
13
each represents an anthryl group, an anthrylphenyl group, a phenanthryl group or a pyrenyl group;
(5) The organic light-emitting device described in the above (1), wherein the compound represented by the formula (1) is utilized as charge-transporting materials;
(6) The organic light-emitting device described in the above (1), wherein the layer comprising the compound represented by the formula (1) is formed by a coating method;
(7) A compound represented by the formula (2) described in the above (2);
(8) The compound described in the above (7), wherein Ar
11
, Ar
12
and Ar
13
each represents an anthryl group, a phenanthryl group, a pyrenyl group, an anthrylphenyl group, a perylenyl group, a chrysenyl group, a triphenylenyl group or groups in which cyclocondensation is further conducted to these structures; and
(9) The compound described in the above (7), wherein Ar
11
, Ar
12
and Ar
13
each represents an anthryl group, an anthrylphenyl group, a phenanthryl group or a pyrenyl group.
DETAILED DESCRIPTION OF THE INVENTION
The invention will be described in detail below.
In formula (1), R
11
, R
12
and R
13
each represents a group having a cyclocondensed polycyclic hydrocarbon structure in which three or more rings are cyclocondensed. The cyclocondensed polycyclic hydrocarbon structures in which three or more rings are cyclocondensed include structures described in Aldrich Structure Index, for example, pages 177 and 178, the 1996 and 1997 editions, Aldrich Co.,
Library of Rare Chemicals Structure Index
, for example, pages 165 to 168, the 1993 edition, Sigma-Aldrich Co., and
Organic Chemistry
-
Biochemistry Nomenclature
, the first volume, pages 21 to 28, translated by Kazuo Hirayama, Nankodo (1988). Examples of the structures include an anthracene structure, a phenanthrene structure, a pyrene structure, a triphenylene structure, a perylene structure, a fluoranthene structure, an indacene structure, an acenaphthylene structure, a fluorene structure, a tetraphenylene structure and structures in which cyclocondensation is further conducted to these structures (for example, a benzanthracene structure, a benzpyrene structure, a pentacene structure, a coronene structure and a chrysene structure).
The cyclocondensed polycyclic hydrocarbon structures in which three or more rings are cyclocondensed are preferably aromatic cyclocondensed hydrocarbon structures in which three or more rings are cyclocondensed, and more preferably an anthracene structure, a phenanthrene structure and a pyrene structure.
R
11
, R
12
and R
13
each has preferably from 14 to 50 carbon atoms, more preferably from 14 to 30 carbon atoms, and still more preferably from 14 to 20 carbon atoms. R
11
, R
12
and R
13
are preferably groups composed of only carbon and hydrogen atoms, and more preferably groups composed of only aromatic hydrocarbon structures. R
11
, R
12
and R
13
are each preferably a substituted or unsubstituted anthryl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted anthrylphenyl group, a substituted or unsubstituted pyrenylphenyl group or a substituted or unsubstituted phenanthrylphenyl group, and more preferably a substituted or unsubstituted anthrylphenyl group, a substituted or unsubstituted pyrenylphenyl group or a substituted or unsubstituted phenanthrylphenyl group. A substituent for R
11
, R
12
or R
13
includes, for example, an R
21
group described later, and is preferably an alkyl group. The term “anthryl” has the same significance as “anthracenyl” and the term “phenanthryl” has the same significance as “phenanthrenyl”.
The compounds represented by formula (1) are preferably compounds represented by formula (3). Formula (3) will be describ
Fuji Photo Film Co. , Ltd.
Sughrue & Mion, PLLC
Yamnitzky Marie
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