Luminescent device with a triarylamine compound

Details Luminescent device with a triarylamine compound Luminescent device with a triarylamine compound

2003-01-23

2004-12-21

Yamnitzky, Marie (Department: 1774)

Stock material or miscellaneous articles

Composite

Of inorganic material

C428S917000, C313S504000

Reexamination Certificate

active

06833200

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a novel triarylamine compound and to a charge-injection-type luminescent device using the same. In particular, the present invention relates to a triarylamine compound applicable to a charge-injection-type luminescent device which directly converts injected charges into optical energy by an applied electric field, and relates to a luminescent device using the same.
2. Description of the Related Art
Pope et al., first discovered electroluminescence (EL) in an organic material, that is, single-crystal anthracene in 1963 (
J. Chem. Phys
., 38, 2042 (1963)). Subsequently, Helfinch and Schneider observed relatively strong EL in an injection EL material containing a solution system having a high injection efficiency in 1965 (
Phys. Rev. Lett
., 14, 229 (1965)).
Many studies of organic luminescent materials containing conjugated organic hosts and conjugated organic activators having condensed benzene rings have been disclosed in U.S. Pat. Nos. 3,172,862, 3,173,050, and 3,710,167
; J. Chem. Phys
., 44, 2902 (1966);
J. Chem. Phys
., 58, 1542 (1973); and
Chem. Phys. Lett
., 36, 345 (1975). Examples of disclosed organic hosts include naphthalene, anthracene, phenanthrene, tetracene, pyrene, benzpyrene, chrysene, picene, carbazole, fluorene, biphenyl, terphenyl, triphenylene oxide, dihalobiphenyl, trans-stilbene, and 1,4-diphenylbutadiene. Examples of disclosed activators include anthracene, tetracene and pentacene. Since these organic luminescent materials are provided as single layers having a thickness of more than 1 &mgr;m, a high electric field is required for luminescence. Under these circumstances, thin film devices formed by a vacuum deposition process have been proposed (for example, “Thin Solid Films” p. 94 (1982);
Polymer
, 24, 748 (1983); and
J. Appl. Phys
., 25, L773 (1986)). Although the thin film devices are effective for reducing the driving voltage, their luminance is far from levels for practical use.
In recent years, Tang, et al., have developed an EL device having a high luminance at a low driving voltage (
Appl. Phys. Lett
., 51, 913 (1987) and U.S. Pat. No. 4,356,429). The EL device is fabricated by depositing two significantly thin layers, that is, a charge transport layer and a luminescent layer, between the anode and the cathode by a vacuum deposition process. Such layered organic EL devices are disclosed in, for example, Japanese Patent Application Laid-Open Nos. 59-194393, 59-194393, 63-264692, and 3-163188, U.S. Pat. Nos. 4,539,507 and 4,720,432, and
Appl. Phys. Lett
., 55, 1467 (1989).
Also, an EL device of a triple-layered structure having independently a carrier transport function and a luminescent ability was disclosed in
Jpn. J. Apply. Phys
., 27, L269 and L713 (1988). Since the carrier transportability is improved in such an EL device, the versatility of possible dyes in the luminescent layer is considerably increased. Further, the device configuration suggests feasibility of improved luminescence by effectively trapping holes and electrons (or excimers) in the central luminescent layer.
Layered organic EL devices are generally formed by vacuum deposition processes. EL devices having considerable luminance are also formed by casting processes (as described in, for example, Extended Abstracts (The 50th Autumn Meeting (1989), p. 1006 and The 51st Autumn Meeting (1990), p. 1041; The Japan Society of Applied Physics). Considerably high luminance is also achieved by a single-layered mixture-type EL device, in which the layer is formed by immersion-coating a solution containing polyvinyl carbazole as a hole transport compound, an oxadiazole derivative as an electron transport compound and coumarin-6 as a luminescent material, as described in Extended Abstracts of the 38th Spring Meeting 1991, p. 1086; The Japan Society of Applied Physics and Related Societies.
As described above, the organic EL devices have been significantly improved and have suggested the feasibility of a wide variety of applications; however, these EL devices have some problems in practical use, for example, insufficient luminance, changes in luminance during prolonged use, and deterioration by atmospheric gas containing oxygen and humidity. Further, the EL devices do not sufficiently satisfy needs for diverse wavelengths of luminescent light for precisely determining luminescent hues of blue, green and red colors in full-color displays, etc.
SUMMARY OF THE INVENTION
It is an object of the present invention to provide an organic compound applicable to a luminescent device having an optical output with significantly high efficiency and luminance.
It is another object of the present invention to provide an organic compound applicable to a luminescent device, which has diverse luminescent wavelengths, a variety of luminescent hues, and significantly high durability.
It is a further object of the present invention to provide a luminescent device easily produced at relatively low production cost and is highly safe.
An aspect of the present invention is a triarylamine compound represented by the following general formula [1]:
wherein R
1
and R
2
are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryl group; Ar
1
, Ar
2
, Ar
3
, and Ar
4
are each a substituted or unsubstituted aryl or heterocyclic group, which may be the same or different from each other; and at least one of Ar
1
, Ar
2
, Ar
3
, and Ar
4
is a fused aromatic ring.
Another aspect of the present invention is a triarylamine compound represented by the following general formula [2]:
wherein R
3
and R
4
are each independently a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryl group; Ar
5
, Ar
6
, Ar
7
, and Ar
8
are each a substituted or unsubstituted aryl or heterocyclic group, which may be the same or different from each other; and at least one of Ar
5
, Ar
6
, Ar
7
, and Ar
8
is a &pgr;-conjugated aromatic hydrocarbon having 12 or more carbon atoms.
A further aspect of the present invention is a luminescent device comprising a pair of electrodes, and at least one compound among the compounds represented by the general formulae [1] or [2] disposed therebetween.
The organic luminescent device in accordance with the present invention is a thin lightweight solid device having a large area and high resolution and capable of high-speed operation, unlike conventional incandescent lamps, fluorescent lamps, and inorganic luminescent diodes, and thus satisfies advanced requirements.


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Chemical Abstracts, vol. 128, No. 26, Jun. 29, 1998 (Abstract No. 328604).
Partridge, R.H., “Electroluminescence from polyvinylcarbazole films: 3. Electroluminescent devices”, Polymer, vol. 24, No. 6, Jun. 1983, pp. 748-754.
Ogawa, T., Wakemoto, H., and Takezaw

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