Organic compounds -- part of the class 532-570 series – Organic compounds – Phosphorus esters
Reexamination Certificate
2002-03-19
2004-09-14
Ramsuer, Robert W. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Phosphorus esters
C558S418000, C558S419000, C558S420000, C558S378000, C564S427000, C564S393000
Reexamination Certificate
active
06790975
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention relates to an aminostyrylanthracene compound suitable as an organic luminescent material emitting any desired color and a synthetic intermediate thereof, and a process for production thereof.
BACKGROUND ART
The organic electroluminescent element (EL element) is recently attracting attention as a candidate for the flat panel display which emits natural light, has a high response speed, and has no dependence on viewing angle. Thus, the organic luminescent material constituting EL elements is arousing acute interest. The first advantage of the organic luminescent material is that its optical properties can be controlled to a certain extent by molecular design. This makes it possible to realize a full-color organic luminescent element made of luminescent materials emitting three primary colors (red, blue, and green) individually.
Styryl compounds represented by the following general formula [A] find use as an organic electroluminescent material and also find use in various applications because they emit intense light (ranging from blue to red in the visible region) depending on the substituent introduced thereinto. In addition, being sublimable, they offer the advantage of forming a uniform amorphous film by vacuum deposition. The present-day molecular orbital calculations permit one to make an approximate prediction of the material's optical properties. In actual, a technology to produce the desired material efficiently is most important for industry.
(where, in the general formula [A] above, Ar represents an aryl group which may have a substituent, R
a
and R
b
each represent a hydrogen atom, a saturated or unsaturated hydrocarbon group, an aryl group which may have a substituent, a cyano group, a halogen atom, a nitro group, a hydrocarbon oxy group, or a hydrocarbon amino group, which may be identical or different.)
Organic luminescent materials produced so far are mostly those compounds represented by the general formula [A] above. Many of them emit light of blue to green, and only a few of them emit light of yellow to red. [The Institute of Electronics, Information and Communication Engineers; Technical Research Report; Organic Electronics, 17, 7 (1992), Inorganic and Organic Electroluminescence 96 Berlin, 101 (1996)] There has been no established method for their efficient production.
SUMMARY OF THE INVENTION
It is an object of the present invention, which was completed in view of the present state mentioned above, to provide a compound suitable for use as an organic luminescent material emitting intense yellow to red light, a synthetic intermediate thereof, and a process for its efficient production.
In order to address the above-mentioned problem, the present inventors carried out extensive studies. As the result, they found that an aminostyrylanthracene compound represented by the general formula [I], [II], [III], or [IV] emits intense light and hence is useful as a luminescent material for yellow to red light, and they also established a general, efficient process for its production.
First, the present invention relates to an aminostyrylanthracene compound represented by the following general formula [I], [II], [III], or [IV]. (referred to as “the compound of the present invention” hereinafter)
[where, in the general formula [I] above, R
2
represents an unsubstituted aryl group, R
1
represents an aryl group represented by the following general formula (1),
(where, in the general formula (1) above, R
6
, R
7
, R
8
, R
9
, and R
10
are identical or different groups, each representing a hydrogen atom, a saturated or unsaturated hydrocarbon oxy group having one or more carbons, a hydrocarbon group, a hydrocarbon amino group, a fluoroalkyl group, or an aryl group which may have a substituent.) R
3
and R
4
are identical or different groups, at least one of them being a hydrogen atom, a cyano group, a fluoroalkyl group, a nitro group, or a halogen atom, and R
5
represents a hydrogen atom, a saturated or unsaturated hydrocarbon group having one or more carbons, or an aryl group which may have a substituent.]
[where, in the general formula [II] above, R
11
and R
12
are identical or different groups, each representing an aryl group represented by the following general formula (2),
(where, in the general formula (2) above, R
16
, R
17
, R
18
, R
19
, and R
20
are identical or different groups, each representing a hydrogen atom, a saturated or unsaturated hydrocarbon oxy group having one or more carbons, a hydrocarbon group, a hydrocarbon amino group, a fluoroalkyl group, or an aryl group which may have a substituent.) R
13
and R
14
are identical or different groups, at least one of them being a hydrogen atom, a cyano group, a fluoroalkyl group, a nitro group, or a halogen atom, and R
15
represents a hydrogen atom, a saturated or unsaturated hydrocarbon group having one or more carbons, or an aryl group which may have a substituent.]
[where, in the general formula [III] above, R
21
represents an aryl group represented by the following general formula (3),
(where, in the general formula (3) above, R
26
, R
27
, R
28
, R
29
, and R
30
are identical or different groups, each representing a hydrogen atom, a saturated or unsaturated hydrocarbon oxy group having one or more carbons, a hydrocarbon group, a hydrocarbon amino group, or a fluoroalkyl group.) R
22
represents an aryl group represented by the following general formula (4),
(where, in the general formula (4) above, R
31
, R
32
, R
33
, R
34
, R
35
, R
36
, and R
37
are identical or different groups, each representing a hydrogen atom, a saturated or unsaturated hydrocarbon oxy group having one or more carbons, a hydrocarbon group, a hydrocarbon amino group, a fluoroalkyl group, or an aryl group which may have a substituent.) R
23
and R
24
are identical or different groups, at least one of them being a hydrogen atom, a cyano group, a fluoroalkyl group, a nitro group, or a halogen atom, and R
25
represents a hydrogen atom, a saturated or unsaturated hydrocarbon group having one or more carbons, or an aryl group which may have a substituent.]
[where, in the general formula [IV] above, R
38
and R
39
are identical or different groups, at least one of them being a hydrogen atom or a saturated or unsaturated hydrocarbon group having one or more carbons, R
40
and R
41
are identical or different groups, each representing a hydrogen atom, a cyano group, a fluoroalkyl group, a nitro group, or a halogen atom, and R
42
represents a hydrogen atom, a saturated or unsaturated hydrocarbon group having one or more carbons, or an aryl group which may have a substituent.]
The compound of the present invention can be effectively used as an organic luminescent material which emits yellow to red light. It has a high glass transition point and a high melting point. It is stable electrically, thermally, and chemically and is amorphous. It easily takes on a glassy state and hence is capable of vapor deposition.
The compound of the present invention should preferably be one which is represented by any of the following general formulas.
[where, in the general formula (5) above, Ar
1
and Ar
2
are identical or different aryl groups which may have a substituent and, if they have a substituent, they represent a group selected from aryl groups represented by the following general formulas (6), (7), (8), (9), (10), and (11).
(where, in the general formulas (6), (7), (8), (9), (10), and (11) above, R
44
, R
45
, and R
46
each represent a saturated or unsaturated hydrocarbon group having one or more carbons (preferably 1 to 6) or a fluoroalkyl group, R
47
, R
48
, R
49
, R
50
, R
51
, and R
52
are identical or different groups, each representing a saturated or unsaturated hydrocarbon group having one or more carbons (preferably 1 to 6 carbons), or a fluoroalkyl group, n is
Ichimura Mari
Ishibashi Tadashi
Tamura Shinichiro
Ramsuer Robert W.
Sackey Ebenezer
Sonnenschein Nath & Rosenthal LLP
Sony Corporation
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