Stock material or miscellaneous articles – Composite – Of inorganic material
Reexamination Certificate
2001-05-22
2003-10-14
Kelly, Cynthia H. (Department: 1774)
Stock material or miscellaneous articles
Composite
Of inorganic material
C428S913000, C313S504000, C313S506000, C564S305000, C564S429000
Reexamination Certificate
active
06632543
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a novel amine compound and an organic electroluminescence device (electroluminescence will be referred to as EL, hereinafter) using the amine compound and, more particularly, to an amine compound useful as a material constituting an organic EL device and an organic EL device which uses the amine compound and has a long life.
BACKGROUND ART
Organic EL devices are studied widely since the organic EL devices are completely solid devices and light weight thin displays driven under a low voltage and planar light sources can be prepared by using such devices.
In the application to displays, the organic EL devices have a drawback in that luminance of light emission decreases in a short time.
To overcome the drawback, improvements in a hole transporting material have been attempted.
For example, as disclosed in U.S. Pat. No. 5,061,569, it is known that the half-life of emission can be improved by using an amine derivative having a condensed aromatic ring such as N,N′-di(naphthyl-1-yl)-N,N′-diphenyl-4,4′-benzidine (referred to as NPD, hereinafter) as the hole transporting material.
However, since the above material has a glass transition temperature (Tg) as low as 100° C., an organic EL device using this material has a drawback in that the organic EL device has a short life time when the organic EL device is stored or used at a high temperature. In other words, the organic EL device has insufficient heat resistance. As another example, it is disclosed in the specification of Japanese Patent Application Laid-Open No. Heisei 8(1996)-48656 that an aromatic diamine derivative having at least biphenyl group as a substituent is used as the hole transporting material.
However, the above material has a drawback in that purification of the material is not easy since biphenyl group is too rigid and solubility of the diamine derivative having biphenyl group in organic solvents is poor. As the result, a material containing a great amount of impurities is obtained in industrial production of the aromatic diamine derivative and an organic EL device using the diamine derivative has insufficient heat resistance.
Moreover, an organic EL device using the above amine derivative has insufficient properties other than the heat resistance such as insufficient luminance of light emission and life time of luminance.
DISCLOSURE OF THE INVENTION
The present invention has been made under the above circumstances and has an object of providing a novel amine compound which has excellent solubility in organic solvents and can be produced easily, an organic EL device using the amine compound which has excellent heat resistance and an organic EL device using the amine compound which exhibits an excellent luminance of light emission and has a long life of luminance.
As the result of extensive studies by the present inventors to achieve the above object, it was found that the object can be achieved by an amine compound having a specific structure. The present invention has been completed based on the knowledge.
The present invention provides:
(1) An amine compound represented by following general formula (I):
(In formula (I), Ar
1
, Ar
2
, Ar
3
and Ar
4
each represent an aryl group having 5 to 30 nuclear atoms which may have substituents, at least one of Ar
1
, Ar
2
, Ar
3
and Ar
4
represents a m-terphenyl group, Ar
5
and Ar
6
each represent an arylene group having 5 to 30 nuclear atoms which may have substituents, X represents O, S, an alkylene group having 1 to 6 carbon atoms, an arylene group having 5 to 30 nuclear atoms or diphenylmethylene group, p and q each represent an integer of 0 to 3, r represents a number of 0 or 1 and p+q≧1);
(2) An amine compound described in (1), wherein at least one of Ar
1
, Ar
2
, Ar
3
and Ar
4
represents a m-terphenyl group and the rest of Ar
1
, Ar
2
, Ar
3
and Ar
4
represent phenyl group or naphthyl group;
(3) An amine compound described in any of (1) and (2), wherein the m-terphenyl group is a group expressed by following formula (II):
(4) An organic EL device comprising at least an organic light emitting layer disposed between a pair of electrodes, which device comprises an amine compound described in any of (1) to (3);
(5) An organic EL device described in (4), which comprises an amine compound described in any of (1) to (3) in a hole transporting area;
(6) An organic EL device described in (4), which comprises an amine compound described in any of (1) to (3) in a hole transporting layer; and
(7) An organic EL device described in any of (4) to (6), which comprises in the organic light emitting area a compound selected from aromatic compounds having a styryl group which are represented by following general formulae (III) to (V):
(In general formula (III), Ar
7
represents an aromatic group having 5 to 40 nuclear atoms which may have substituents, Ar
8
, Ar
9
and Ar
10
each represent hydrogen atom or an aryl group having 5 to 30 nuclear atoms which may have substituents, at least one of Ar
8
, Ar
9
and Ar
10
represents an aryl group which may have substituents and n represents an integer of 1 to 6)
(In general formula (IV), Ar
11
represents an aromatic group having 5 to 30 nuclear atoms which may have substituents, Ar
12
and Ar
13
each represent hydrogen atom or an aryl group having 5 to 30 nuclear atoms which may have substituents, at least one of the groups represented by Ar
11
, Ar
12
and Ar
13
is substituted with a styryl group which may have substituents and m represents an integer of 1 to 6), and
(In general formula (V), Ar
14
and Ar
20
each represent an aryl group having 5 to 30 nuclear atoms which may have substituents, Ar
15
to Ar
19
each represent hydrogen atom or an aromatic group having 5 to 30 nuclear atoms which may have substituents, at least one of the groups represented by Ar
15
to Ar
19
is substituted with a styryl group which may have substituents and s, t, u, and v each represent a number of 0 or 1).
THE MOST PREFERRED EMBODIMENT TO CARRY OUT THE INVENTION
The organic compound of the present invention is a compound represented by the general formula (I):
In the above general formula (I), Ar
1
, Ar
2
, Ar
3
and Ar
4
each represent an aryl group having 5 to 30 nuclear atoms which may have substituents and at least one of Ar
1
, Ar
2
, Ar
3
and Ar
4
represents a m-terphenyl group
Examples of the aryl group having 5 to 30 nuclear atoms include phenyl group, biphenyl group, naphthyl group, anthranyl group, terphenyl group, phenanthryl group, pyrenyl group, chrysenyl group, pyrrolyl group, furanyl group, thiophenyl group, oxazolyl group, oxadiazolyl group, benzofuranyl group, carbazolyl group, isobenzolyl group, quinolyl group, pyrimidyl group and quinoxanyl group. Among these groups, phenyl group, naphthyl group, biphenyl group, anthranyl group, phenanthryl group and terphenyl group are preferable and phenyl group and naphthyl group are more preferable.
The above groups represented by Ar
1
, Ar
2
, Ar
3
and Ar
4
may be the same with or different from each other. It is necessary that at least one of the groups represented by Ar
1
, Ar
2
, Ar
3
and Ar
4
be a m-terphenyl group which may have substituents.
The m-terphenyl group present in the amine compound represented by general formula (I) of the present invention is a monovalent group obtained by removing one hydrogen atom from a m-terphenyl composed of three benzene rings which are not condensed and bonded to each other in a manner such that the central benzene ring is bonded to the other two benzene rings at the m-positions.
Therefore, the m-terphenyl group is represented by general formula (II′). Nitrogen atom may be bonded at various positions in the m-terphenyl group. Compounds represented by general formula (II′) in which nitrogen atom is bonded at the 3-, 4-, 5-, 2′- or 5′-position are easily available. Among these compounds, the compound in which nitrogen atom is bonded at the 4-position, i.e., the m-terphenyl expressed by formula (II), is preferably
Idemitsu Kosan Co. Ltd.
Kelly Cynthia H.
Thompson Camine S
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