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1. 发明授权

US08252431B2 Compound wherein substituted bipyridyl group is connected with pyridoindole ring structure through phenylene group, and organic electroluminescent device 有权
标题翻译：其中取代的联吡啶基通过亚苯基与吡啶并吲哚环结构连接的化合物和有机电致发光器件
公开(公告)号：US08252431B2
公开(公告)日：2012-08-28
申请号：US12531365
申请日：2008-03-13
申请人： Norimasa Yokoyama , Shuichi Hayashi , Shigeru Kusano , Makoto Nagaoka
发明人： Norimasa Yokoyama , Shuichi Hayashi , Shigeru Kusano , Makoto Nagaoka
IPC分类号： H01L51/54
CPC分类号： H01L51/0072 , C07D471/04 , C07D519/00 , C09K11/06 , C09K2211/1007 , C09K2211/1011 , C09K2211/1029 , H01L51/0067 , H01L51/5048
摘要： An organic compound is provided having excellent electron-injection/transport performance, hole-blocking ability, and high stability in a thin-film state. An organic electroluminescence device having a high efficiency and a high durability is provided, using the compound. The compound has a substituted bipyridyl group and a pyridoindole ring structure connected with each other through a phenylene group, is of formula (1). The organic EL device has a pair of electrodes and at least one organic layer interposed between the electrodes, wherein the compound is a constituent material for an organic layer therein.
摘要翻译：提供了具有优异的电子注入/输送性能，空穴阻断能力和在薄膜状态下的高稳定性的有机化合物。使用该化合物，提供具有高效率和高耐久性的有机电致发光器件。化合物具有通过亚苯基相互连接的取代的联吡啶基和吡啶并吲哚环结构，具有式（1）。有机EL器件具有一对电极和介于电极之间的至少一个有机层，其中该化合物是其中有机层的构成材料。

2. 发明申请

US20110175079A1 COMPOUND HAVING SUBSTITUTED ANTHRACENE RING STRUCTURE AND PYRIDOINDOLE RING STRUCTURE AND ORGANIC ELECTROLUMINESCENCE DEVICE 有权
标题翻译：具有取代的蒽环结构和吡啶环结构和有机电致发光器件的化合物
公开(公告)号：US20110175079A1
公开(公告)日：2011-07-21
申请号：US13120665
申请日：2009-09-18
申请人： Norimasa Yokoyama , Shuichi Hayashi , Sawa Izumi , Naoaki Kabasawa , Shigeru Kusano
发明人： Norimasa Yokoyama , Shuichi Hayashi , Sawa Izumi , Naoaki Kabasawa , Shigeru Kusano
IPC分类号： H01L51/54 , C07D471/04
CPC分类号： H01L51/0072 , C07D471/04 , C09K11/06 , C09K2211/1011 , C09K2211/1014 , C09K2211/1029 , H01L51/0058 , H01L51/0059 , H01L51/0067 , H01L51/5048 , H01L51/5092 , H05B33/14
摘要： The present invention provides an organic compound having excellent properties, which is excellent in electron-injection/transport performance, has hole-blocking ability and is high stability in a thin-film state, as a material for an organic electroluminescence device having a high efficiency and a high durability, and provides is an organic electroluminescence device having a high efficiency and a high durability using the compound. The present invention relates to a compound having a substituted anthracene ring structure and a pyridoindole ring structure represented by general formula (1); and an organic electroluminescence device having a pair of electrodes and at least one organic layer interposed between the electrodes in which the at least one organic layer contains the compound.
摘要翻译：本发明提供了具有优异的电子注入/输送性能的具有优异的空穴阻挡能力和在薄膜状态下的高稳定性的有机化合物作为具有高效率的有机电致发光器件的材料并且具有高耐久性，并且提供了使用该化合物具有高效率和高耐久性的有机电致发光器件。本发明涉及具有取代的蒽环结构的化合物和由通式（1）表示的吡啶并吲哚环结构。以及有机电致发光器件，其具有一对电极和插入在电极之间的至少一个有机层，其中至少一个有机层含有该化合物。

3. 发明申请

US20090230849A1 COMPOUND HAVING OXADIAZOLE RING STRUCTURE BONDED WITH AROMATIC HETEROCYCLIC RING AND ORGANIC ELECTROLUMINESCENT DEVICE 有权
标题翻译：具有与芳香环氧环和有机电致发光器件结合的氧杂环唑结构的化合物
公开(公告)号：US20090230849A1
公开(公告)日：2009-09-17
申请号：US12066508
申请日：2006-09-12
申请人： Tetsuzo Miki , Norimasa Yokoyama , Shuichi Hayashi , Shigeru Kusano , Yoshio Taniguchi , Musubu Ichikawa
发明人： Tetsuzo Miki , Norimasa Yokoyama , Shuichi Hayashi , Shigeru Kusano , Yoshio Taniguchi , Musubu Ichikawa
IPC分类号： H01J1/63 , C07D471/02 , C07D413/02
CPC分类号： H01L51/007 , C07D413/14 , C07D417/14 , C07D471/04 , C07D519/00 , C09K11/06 , C09K2211/1029 , C09K2211/1037 , C09K2211/1044 , C09K2211/1048 , H01L51/0067 , H01L51/0068 , H01L51/0069 , H01L51/0071 , H01L51/0072 , H01L51/5012 , H01L51/5048 , H05B33/14
摘要： An object of the invention is to provide an organic compound having excellent characteristics as a material for highly efficient and highly durable organic EL devices, and also to provide a highly efficient and highly durable organic EL device. This invention relates to a compound represented by the general formula (1) having an oxadiazole ring structure bonded with an aromatic heterocycle, and to an organic electroluminescence device containing the compound: wherein Ar represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; A represents a substituted or unsubstituted aromatic heterocyclic group; and n represents an integer of 1 to 3.
摘要翻译：本发明的目的是提供一种具有优异特性的有机化合物作为用于高效率和高度耐用的有机EL器件的材料，并且还提供高效率和高度耐用的有机EL器件。本发明涉及具有与芳族杂环结合的恶二唑环结构的由通式（1）表示的化合物和含有该化合物的有机电致发光器件：其中Ar表示取代或未取代的芳族烃基，取代或未取代的芳族杂环基或取代或未取代的稠合多环芳基; A表示取代或未取代的芳族杂环基; n表示1〜3的整数。

4. 发明授权

US08247087B2 Compound having oxadiazole ring structure bonded with aromatic heterocyclic ring and organic electroluminescent device 有权
标题翻译：具有与芳族杂环键合的恶二唑环结构的化合物和有机电致发光器件
公开(公告)号：US08247087B2
公开(公告)日：2012-08-21
申请号：US12066508
申请日：2006-09-12
申请人： Tetsuzo Miki , Norimasa Yokoyama , Shuichi Hayashi , Shigeru Kusano , Yoshio Taniguchi , Musubu Ichikawa
发明人： Tetsuzo Miki , Norimasa Yokoyama , Shuichi Hayashi , Shigeru Kusano , Yoshio Taniguchi , Musubu Ichikawa
IPC分类号： H01L51/54
CPC分类号： H01L51/007 , C07D413/14 , C07D417/14 , C07D471/04 , C07D519/00 , C09K11/06 , C09K2211/1029 , C09K2211/1037 , C09K2211/1044 , C09K2211/1048 , H01L51/0067 , H01L51/0068 , H01L51/0069 , H01L51/0071 , H01L51/0072 , H01L51/5012 , H01L51/5048 , H05B33/14
摘要： An object of the invention is to provide an organic compound having excellent characteristics as a material for highly efficient and highly durable organic EL devices, and also to provide a highly efficient and highly durable organic EL device. This invention relates to a compound represented by the general formula (1) having an oxadiazole ring structure bonded with an aromatic heterocycle, and to an organic electroluminescence device containing the compound: wherein Ar represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; A represents a substituted or unsubstituted aromatic heterocyclic group; and n represents an integer of 1 to 3.
摘要翻译：本发明的目的是提供一种具有优异特性的有机化合物作为用于高效率和高度耐用的有机EL器件的材料，并且还提供高效率和高度耐用的有机EL器件。本发明涉及具有与芳族杂环结合的恶二唑环结构的由通式（1）表示的化合物和含有该化合物的有机电致发光器件：其中Ar表示取代或未取代的芳族烃基，取代或未取代的芳族杂环基或取代或未取代的稠合多环芳基; A表示取代或未取代的芳族杂环基; n表示1〜3的整数。

5. 发明申请

US20120161107A1 ORGANIC ELECTROLUMINESCENT DEVICE 有权
标题翻译：有机电致发光器件
公开(公告)号：US20120161107A1
公开(公告)日：2012-06-28
申请号：US12737099
申请日：2009-06-09
申请人： Norimasa Yokoyama , Shigeru Kusano , Shuichi Hayashi
发明人： Norimasa Yokoyama , Shigeru Kusano , Shuichi Hayashi
IPC分类号： H01L51/54
CPC分类号： C07D401/14 , C07D213/22 , H01L51/0059 , H01L51/0067 , H01L51/0072 , H01L51/5048 , H01L51/5088
摘要： [Problem] To provide an organic EL device having high efficiency, low driving voltage and long life by combining various materials for the organic EL device which are excellent in hole and electron injection/transport performances, stability as a thin film and durability.[Means for Resolution] An organic electroluminescent device comprising at least an anode electrode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode electrode in this order, wherein the hole injection layer comprises an arylamine compound having at least three triphenylamine structures in the molecule, the hole transport layer comprises an arylamine compound having two triphenylamine structures in the molecule, and the electron transport layer comprises a substituted bipyridyl compound represented by the following general formula (1): wherein R1 to R7 may be the same or different, and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having from 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; n1 is an integer of from 2 to 4; A1 represents a di- to tetra-valent substituted or unsubstituted aromatic hydrocarbon groups, a di- to tetra-valent substituted or unsubstituted aromatic heterocyclic groups, a di- to tetra-valent substituted or unsubstituted condensed polycyclic aromatic group or a trivalent group represented by the following general formula (2): wherein X, Y and Z each represents a carbon atom or a nitrogen atom, provided that when n1=2, two bipyridyl structures can directly bond to each other, and in that case, A1 is absent.
摘要翻译：通过组合具有优异的空穴和电子注入/输送性能的有机EL器件的各种材料，作为薄膜的稳定性和耐久性，提供了具有高效率，低驱动电压和长寿命的有机EL器件。 [解决方法]依次包括至少阳极，空穴注入层，空穴传输层，发光层，电子传输层和阴极电极的有机电致发光器件，其中空穴注入层包括在分子中具有至少三个三苯胺结构的芳基胺化合物，空穴传输层包含分子中具有两个三苯胺结构的芳基胺化合物，电子传输层包含由以下通式（1）表示的取代的联吡啶基化合物：其中R 1 R 7可以相同或不同，表示氢原子，氟原子，氯原子，氰基，三氟甲基，具有1〜6个碳原子的直链或支链烷基，取代或未取代的芳香族烃基，取代或未取代的芳族杂环基，或取代或未取代的缩合多环芳香族; n1为2〜4的整数， A1表示二价至四价的取代或未取代的芳香族烃基，二价至四价的取代或未取代的芳族杂环基，二价至四价的取代或未取代的稠合多环芳香族基或三价以下通式（2）：其中X，Y和Z各自表示碳原子或氮原子，条件是当n1 = 2时，两个联吡啶基结构可以直接键合，在这种情况下不存在。

6. 发明授权

US08168308B2 Compound having pyridoindole ring structure having substituted pyridyl group attached thereto, and organic electroluminescence element 有权
标题翻译：具有连接有取代的吡啶基的吡啶并吲哚环结构的化合物和有机电致发光元件
公开(公告)号：US08168308B2
公开(公告)日：2012-05-01
申请号：US12377908
申请日：2007-08-16
申请人： Norimasa Yokoyama , Shuichi Hayashi , Shigeru Kusano
发明人： Norimasa Yokoyama , Shuichi Hayashi , Shigeru Kusano
IPC分类号： H01L51/54 , C07D471/00
CPC分类号： C09K11/06 , C07D471/04 , C07D519/00 , C09K2211/1007 , C09K2211/1011 , C09K2211/1029 , C09K2211/1044 , H01L51/0072 , H01L51/0081 , H01L51/5048 , H01L51/5096 , H05B33/14 , Y10S428/917
摘要： The present invention is to provide an organic compound having excellent characteristics as a material for an organic EL device having a high efficiency and a high durability, and to provide an organic EL device having a high efficiency and a high durability by using the compound. The invention relates to a compound having a pyridoindole ring structure having a substituted pyridyl group attached thereto, which is represented by the general formula (1); and to an organic electroluminescent device comprising a pair of electrodes and at least one organic layer interposed between the electrodes, wherein at least one of the organic layer(s) contains the compound: wherein Ar represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; R1 to R10 may be the same or different from one another and each independently represents a hydrogen atom, a fluorine atom, a cyano group, an alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group; Z represents a 6-membered aromatic heterocyclic ring containing one nitrogen atom; and m and n each independently represents an integer of 1 to 3, provided that n is 1 when m is 2 or 3.
摘要翻译：本发明提供一种具有优异特性的有机化合物作为具有高效率和高耐久性的有机EL器件的材料，并且通过使用该化合物来提供具有高效率和高耐久性的有机EL器件。本发明涉及具有通式（1）表示的具有取代的吡啶基的吡啶并吲哚环结构的化合物。以及包含一对电极和介于所述电极之间的至少一个有机层的有机电致发光器件，其中所述有机层中的至少一个含有所述化合物：其中Ar表示取代或未取代的芳族烃基，取代的或未取代的芳族杂环基，或取代或未取代的稠合多环芳基; R 1〜R 10可以相同也可以不同，各自独立地表示氢原子，氟原子，氰基，烷基或取代或未取代的芳香族烃基。 Z表示含有一个氮原子的6元芳族杂环; m和n各自独立地表示1〜3的整数，条件是当m为2或3时n为1。

7. 发明申请

US20110006291A1 COMPOUND HAVING SUBSTITUTED PYRIDYL GROUP AND PYRIDOINDOLE RING STRUCTURE LINKED THROUGH PHENYLENE GROUP, AND ORGANIC ELECTROLUMINESCENT DEVICE 有权
标题翻译：具有取代的吡啶基的化合物和通过苯乙烯基团连接的吡啶环结构和有机电致发光器件
公开(公告)号：US20110006291A1
公开(公告)日：2011-01-13
申请号：US12865736
申请日：2009-01-30
申请人： Norimasa Yokoyama , Shuichi Hayashi , Sawa Izumi , Shigeru Kusano
发明人： Norimasa Yokoyama , Shuichi Hayashi , Sawa Izumi , Shigeru Kusano
IPC分类号： H01L51/54 , C07D471/04
CPC分类号： C07D471/04 , C09K11/06 , C09K2211/1007 , C09K2211/1011 , C09K2211/1029 , H01L51/0052 , H01L51/0072 , H01L51/5012 , H01L51/5048
摘要： Objects of the present invention are to provide an organic compound having excellent properties, which is excellent in electron-injecting/transporting performances, has hole-blocking ability and is highly stable in a thin-film state, as a material for an organic electroluminescent device having a high efficiency and a high durability; and to provide an organic electroluminescent device having a high efficiency and a high durability using the compound. The invention relates to a compound having a substituted pyridyl group and a pyridoindole ring structure linked through a phenylene group, which is represented by the general formula (1); and an organic EL device comprising a pair of electrodes and at least one organic layer interposed between the electrodes, wherein the at least one organic layer contains the compound: wherein Ar represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; R1 to R14 may be the same or different from each other and each represents a hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a trifluoromethyl group, a linear or branched alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group; n represents an integer of 1 to 3; and W, X, Y, and Z respectively represent a carbon atom or a nitrogen atom, provided that only one of W, X, Y, and Z represents a nitrogen atom, and the nitrogen atom does not have the substituent of R7, R8, R9, or R10).
摘要翻译：本发明的目的是提供具有优异的电子注入/传输性能的具有优异的性能的有机化合物，具有空穴阻挡能力并且在薄膜状态下是高度稳定的，作为有机电致发光器件的材料具有高效率和高耐久性; 并提供使用该化合物具有高效率和高耐久性的有机电致发光器件。本发明涉及由通式（1）表示的具有取代的吡啶基和通过亚苯基连接的吡啶并吲哚环结构的化合物。以及包含一对电极和插入在所述电极之间的至少一个有机层的有机EL器件，其中所述至少一个有机层包含化合物：其中Ar表示取代或未取代的芳香族烃基，取代或未取代的芳族杂环基，或取代或未取代的稠合多环芳基; R 1〜R 14可以相同也可以不同，表示氢原子，氟原子，氯原子，氰基，三氟甲基，碳原子数1〜6的直链或支链烷基，取代基或未取代的芳香族烃基，取代或未取代的芳香族杂环基或取代或未取代的稠合多环芳香族基; n表示1〜3的整数， W，X，Y和Z分别表示碳原子或氮原子，只要W，X，Y和Z中只有一个表示氮原子，氮原子不具有R7，R8的取代基，R9或R10）。

8. 发明授权

US08771841B2 Organic electroluminescent device 有权
标题翻译：有机电致发光器件
公开(公告)号：US08771841B2
公开(公告)日：2014-07-08
申请号：US12993051
申请日：2009-05-15
申请人： Norimasa Yokoyama , Shigeru Kusano , Shuichi Hayashi
发明人： Norimasa Yokoyama , Shigeru Kusano , Shuichi Hayashi
IPC分类号： H01L51/54
CPC分类号： H01L51/006 , C07D471/04 , C09K11/06 , C09K2211/1014 , H01L51/0052 , H01L51/0059 , H01L51/0067 , H01L51/0072 , H01L51/5048
摘要： A problem of the invention is to provide an organic EL device having a high efficiency, a low driving voltage and a long life, by combining various materials for organic EL device, which are excellent in an injection or transportation performance of holes or electrons, and in stability and durability in a thin film, so as to enable the respective materials to effectively reveal their characteristics. The invention relates to an organic electroluminescent device including at least an anode electrode, a hole-injecting layer, a hole-transporting layer, an emitting layer, an electron-transporting layer and a cathode electrode in this order, in which the hole-injecting layer contains an arylamine compound having, in its molecule, a structure in which three or more triphenylamine structures are connected through a single bond or a hetero atom-free divalent group; and the hole-transporting layer contains an arylamine compound having two triphenylamine structures in its molecule.
摘要翻译：本发明的一个问题是通过组合空穴或电子的注入或输送性能优异的有机EL器件的各种材料，提供具有高效率，低驱动电压和长寿命的有机EL器件，以及在薄膜中的稳定性和耐久性，以使各种材料能够有效地揭示其特性。本发明涉及一种有机电致发光器件，其中至少具有阳极电极，空穴注入层，空穴传输层，发光层，电子传输层和阴极电极，其中空穴注入在其分子中含有其中三个或更多个三苯胺结构通过单键或无杂原子的二价基团连接的结构的芳基胺化合物; 并且空穴传输层在其分子中含有具有两个三苯胺结构的芳基胺化合物。

9. 发明申请

US20130328040A1 ORGANIC ELECTROLUMINESCENT DEVICE 有权
标题翻译：有机电致发光器件
公开(公告)号：US20130328040A1
公开(公告)日：2013-12-12
申请号：US14001560
申请日：2012-02-24
申请人： Norimasa Yokoyama , Shuichi Hayashi , Eiji Takahashi , Shigeru Kusano
发明人： Norimasa Yokoyama , Shuichi Hayashi , Eiji Takahashi , Shigeru Kusano
IPC分类号： H01L51/00
CPC分类号： H01L51/0072 , C07C211/54 , C07C211/56 , C07C211/58 , C07C2601/14 , C07C2603/18 , C09K11/06 , C09K2211/1007 , C09K2211/1011 , C09K2211/1014 , C09K2211/1029 , H01L51/0059 , H01L2251/308 , H05B33/10 , H05B33/14
摘要： An organic electroluminescent device comprising, between an anode and a cathode, a hole-transporting layer, a luminous layer and an electron-transporting layer, wherein the hole-transporting layer contains an arylamine compound (X) having a molecular structure to which three or more triphenylamine skeletons are singly bonded or bonded through a divalent hydrocarbon group and an arylamine compound (Y) having a molecular structure to which two triphenylamine skeletons are singly bonded or bonded through the divalent hydrocarbon group. The device excels in hole and electron injection/transport property, stability and durability in the form of thin films, and is highly efficient, becomes luminous on a low driving voltage, and has a long life.
摘要翻译：一种在阳极和阴极之间包含空穴传输层，发光层和电子传输层的有机电致发光器件，其中空穴传输层含有具有分子结构的芳基胺化合物（X），其中三个或更多的三苯胺骨架通过二价烃基和具有两个三苯基胺骨架通过二价烃基单键或键合的分子结构的芳基胺化合物（Y）单键或键合。该器件在空穴和电子注入/传输性能，薄膜形式的稳定性和耐久性方面优异，并且高效率，在低驱动电压下变得发光，并且具有长的使用寿命。

10. 发明授权

US08377573B2 Compound having substituted pyridyl group and pyridoindole ring structure linked through phenylene group, and organic electroluminescent device 有权
标题翻译：具有通过亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物和有机电致发光器件
公开(公告)号：US08377573B2
公开(公告)日：2013-02-19
申请号：US12865736
申请日：2009-01-30
申请人： Norimasa Yokoyama , Shuichi Hayashi , Sawa Izumi , Shigeru Kusano
发明人： Norimasa Yokoyama , Shuichi Hayashi , Sawa Izumi , Shigeru Kusano
IPC分类号： H01L51/50
CPC分类号： C07D471/04 , C09K11/06 , C09K2211/1007 , C09K2211/1011 , C09K2211/1029 , H01L51/0052 , H01L51/0072 , H01L51/5012 , H01L51/5048
摘要： Provided is a compound having a substituted pyridyl group and a pyridoindole ring structure linked through a phenylene group, having formula (1), and an organic EL device with a pair of electrodes and at least one organic layer interposed between the electrodes, wherein the at least one organic layer having the compound:
摘要翻译：提供具有通过具有式（1）的亚苯基连接的取代的吡啶基和吡啶并吲哚环结构的化合物和具有一对电极和插入在电极之间的至少一个有机层的有机EL器件，其中在具有化合物的至少一个有机层：

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