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  Aromatic amine derivatives and organic electroluminescent device using sameUSPTO Application #: 20080108832Title: Aromatic amine derivatives and organic electroluminescent device using same Abstract: The present invention provides a novel aromatic amine derivative having a specific structure and an organic electroluminescence device in which an organic thin film layer comprising a single layer or plural layers including at least a light emitting layer is interposed between a cathode and an anode, wherein at least one layer in the above organic thin film layer, particularly a hole injecting layer contains the aromatic amine derivative described above in the form of a single component or a mixed component. Use of the aromatic amine derivative described above materialize an organic electroluminescence device which reduces an operating voltage and makes molecules less liable to be crystallized and which enhances a yield in producing the organic EL device and has a long lifetime. (end of abstract) Agent: Oblon, Spivak, Mcclelland Maier & Neustadt, P.c. - Alexandria, VA, US Inventors: Nobuhiro Yabunouchi, Masahiro Kawamura, Hisayuki Kawamura, Chishio Hosokawa, Shigeyuki Matsunami, Tadahiko Yoshinaga, Yasunori Kijima USPTO Applicaton #: 20080108832 - Class: 549059000 (USPTO) Related Patent Categories: Organic Compounds -- Part Of The Class 532-570 Series, Azo Compounds Containing Formaldehyde Reaction Product As The Coupling Component, Carbohydrates Or Derivatives, Sulfur Containing Hetero Ring (e.g., Thiiranes, Etc.), The Hetero Ring Is Five-membered, Additional Hetero Ring Containing The Patent Description & Claims data below is from USPTO Patent Application 20080108832. Brief Patent Description - Full Patent Description - Patent Application Claims
BACKGROUND OF THE INVENTION [0001] The present invention relates to an aromatic amine derivative and an organic electroluminescence (EL) device using the same, specifically to an aromatic amine derivative which reduces the operating voltage and inhibits the molecules from being crystallized by using an aromatic amine derivative having a specific substituent for a hole transporting material and which enhances a yield in producing an organic EL device and improves a lifetime of the organic EL device. RELATED ART [0002] An organic EL device is a spontaneous light emitting device making use of the principle that a fluorescent substance emits light by recombination energy of holes injected from an anode and electrons injected from a cathode by applying an electric field. Since an organic EL device of a laminate type driven at a low voltage was reported by C. W. Tang et al. of Eastman Kodak Company (C. W. Tang and S. A. Vanslyke, Applied Physics Letters, Vol. 51, p. 913, 1987 and the like), researches on organic EL devices comprising organic materials as structural materials have actively been carried out. Tang et al. use tris(8-quinolinolate)aluminum for the light emitting layer and a triphenyldiamine derivative for the hole transporting layer. The advantages of the laminate structure include an elevation in an efficiency of injecting holes into a light emitting layer, a rise in a production efficiency of excitons produced by blocking electrons injected from a cathode to recombine them and shutting up of excitons produced in a light emitting layer. As shown in the above example, a two-layer type comprising a hole transporting (injecting) layer and an electron transporting and light emitting layer and a three-layer type comprising a hole transporting (injecting) layer, a light emitting layer and an electron transporting (injecting) layer are well known as the device structures of an organic EL device. In such laminate type structural devices, device structures and forming methods are studied in order to enhance a recombination efficiency of holes and electrons injected. [0003] Usually, when an organic EL device is operated or stored under high temperature environment, brought about are adverse effects such as a change in a color of emitted light, a reduction in a current efficiency, a rise in an operating voltage and a reduction in an emission lifetime. A glass transition temperature (Tg) of a hole transporting material has to be raised in order to prevent the above matters. Accordingly, the hole transporting material has to have a lot of aromatic groups in a molecule (for example, aromatic diamine derivatives described in Patent Document 1 and aromatic fused ring diamine derivatives described in Patent Document 2), and usually structures having 8 to 12 benzene rings are preferably used. [0004] However, if they have a lot of aromatic groups in a molecule, crystallization is liable to be caused in forming a thin film using the above hole transporting materials to produce an organic EL device, and the problems that an outlet of a crucible used for vapor deposition is clogged and that defects of a thin film originating in crystallization are caused to bring about a reduction in a yield of an organic EL device have been brought about. Further, compounds having more aromatic groups in a molecule have usually a higher glass transition temperature (Tg) but have a higher sublimation temperature, and it is considered that the phenomena that decomposition is caused in vapor deposition and that a deposited film is unevenly formed are brought about, so that the problem that the lifetime is short has been involved therein. [0005] On the other hand, a publicly known document in which asymmetric aromatic amine derivatives are disclosed is available. For example, aromatic amine derivatives having an asymmetric structure are described in Patent Document 3, but no specific examples are found therein, and the characteristics of the asymmetric compounds are not described therein at all. Further, the examples of asymmetric aromatic amine derivatives having phenanthrene are described in Patent Document 4, but they are handled on the same basis as symmetric compounds, and the characteristics of the asymmetric compounds are not described therein at all. Also, a specific synthetic process is necessary for the asymmetric compounds, but descriptions on the production processes of the asymmetric compounds are not clearly shown in the above patents. Further, a production process of aromatic amine derivatives having an asymmetric structure is described in Patent Document 5, but the characteristics of the asymmetric compounds are not described therein. Thermally stable asymmetric compounds having a high glass transition temperature are described in Patent Document 6, but only examples of compounds having carbazole are shown. [0006] Further, amine compounds having thiophene are reported in Patent Documents 7 to 8, but they are compounds in which diamine compounds have thiophene in a central skeleton thereof. Also, thiophene is bonded directly to amine in Patent Document 7. Compounds having thiophene at en end of diamine compounds are reported in Patent Documents 9 to 10, but they are compounds in which thiophene is bonded directly to amine. These compounds are unstable and hard to be refined, and therefore a purity thereof is not enhanced. When thiophene is bonded directly to amine, an electron state of amine is varied to a large extent, and therefore the satisfactory performances are not exhibited. On the other hand, compounds in which thiophene is bonded to amine via an aryl group are described in Patent Document 11. However, these compounds assume a structure in which thiophene is not substituted to a 2-position or a 3-position. A 2-position or a 3-position in thiophene has a high reactivity and is electrically unstable. Accordingly, if it is present in a molecule, the voltage is elevated in evaluation of the device, and therefore it is not preferred. Polymer amines are described in Patent Document 12, but only specific examples are shown, and the characteristics of amine compounds in which thiophene is bonded to nitrogen via an aryl group are not described therein at all. Compounds having a form of polymers are described in Patent Documents 13 to 22, but they can not be vapor-deposited. Further, polar groups necessary for polymerization reduce the performances of the device such as a lifetime and the like, and therefore the above compounds are not preferred. [0007] As described above, it is usually known that the compounds having a thiophene structure have a high mobility, but the satisfactory performances are not exhibited merely by combining it with an amine structure. Accordingly, an organic EL device having more excellent performances has been strongly required to be developed. Patent Document 1: U.S. Pat. No. 4,720,432 Patent Document 2: U.S. Pat. No. 5,061,569 Patent Document 3: Japanese Patent Application Laid-Open No. 48656/1996 Patent Document 4: Japanese Patent Application Laid-Open No. 135261/1999 Patent Document 5: Japanese Patent Application Laid-Open No. 171366/2003 Patent Document 6: U.S. Pat. No. 6,242,115 Patent Document 7: WO2004-058740 Patent Document 8: Japanese Patent Application Laid-Open No. 304466/1992 Patent Document 9: WO2001-053286 Patent Document 10: Japanese Patent Application Laid-Open No. 287408/1995 Patent Document 11: Japanese Patent Application Laid-Open No. 267972/2003 Patent Document 12: Japanese Patent Application Laid-Open No. 155705/2004 Patent Document 13: Japanese Patent Application Laid-Open No. 042004/2005 Patent Document 14: Japanese Patent Application Laid-Open No. 259441/2005 Patent Document 15: Japanese Patent Application Laid-Open No. Continue reading... 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