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21. 发明授权

US09732036B2 Compound having carbazole ring structure, and organic electroluminescent device 有权
公开(公告)号：US09732036B2
公开(公告)日：2017-08-15
申请号：US13391956
申请日：2010-08-25
申请人： Norimasa Yokoyama , Makoto Nagaoka , Kazunori Togashi , Shigeru Kusano
发明人： Norimasa Yokoyama , Makoto Nagaoka , Kazunori Togashi , Shigeru Kusano
IPC分类号： H01L51/50 , C07D209/86 , C07D209/88 , C07D401/14 , C07D405/10 , C07D409/14 , C07D413/14 , C07D417/14 , C07D471/04 , C09K11/06 , H01L51/00 , H05B33/14
CPC分类号： C07D209/86 , C07D209/88 , C07D401/14 , C07D405/10 , C07D409/14 , C07D413/14 , C07D417/14 , C07D471/04 , C09K11/06 , C09K2211/1029 , H01L51/0061 , H01L51/5012 , H01L51/5016 , H01L51/5056 , H01L51/5096 , H05B33/14
摘要： [Problem]An organic compound of excellent characteristics is provided that exhibits excellent hole-injecting/transporting performance with electron blocking ability, and that has high stability in the thin-film state and high luminous efficiency, the organic compound being provided as material for an organic electroluminescent device having high efficiency and high durability. The invention also provides a high-efficient, high-durable organic electroluminescent device using the compound.[Means for Resolution] The compound is of the following general formula having a carbazole ring structure. The organic electroluminescent device includes a pair of electrodes, and one or more organic layers sandwiched between the pair of electrodes, and the compound is used as a constituent material of at least one organic layer.

22. 发明申请

US20120292609A1 COMPOUND HAVING TRIPHENYLAMINE STRUCTURE, AND ORGANIC ELECTROLUMINESCENT DEVICE 有权
标题翻译：具有三苯胺结构的化合物和有机电致发光器件
公开(公告)号：US20120292609A1
公开(公告)日：2012-11-22
申请号：US13574923
申请日：2011-01-25
申请人： Norimasa Yokoyama , Makoto Nagaoka , Kouki Kase , Shingo Ozawa , Shigeru Kusano
发明人： Norimasa Yokoyama , Makoto Nagaoka , Kouki Kase , Shingo Ozawa , Shigeru Kusano
IPC分类号： H01L51/54 , C07D403/12 , C07D401/12 , C07C217/92 , C07C211/54 , C07C217/80
CPC分类号： H01L51/0059 , C07B2200/05 , C07C211/54 , C07C211/56 , C07C2603/18 , C07D209/86 , C09K11/06 , C09K2211/1014 , H01L51/5048 , H01L51/5088 , H01L51/5096
摘要： There is provided an organic compound of excellent characteristics that exhibits excellent hole-injecting/transporting performance and has an electron blocking ability and a highly stable thin-film state with excellent heat resistance. The compound of the present invention is an arylamine compound having a triphenylamine structure. The arylamine compound is used as a constituent material of at least one organic layer in an organic electroluminescent device that includes a pair of electrodes, and one or more organic layers sandwiched between the pair of electrodes.
摘要翻译：提供具有优异的空穴注入/输送性能，具有优异的耐热性的电子阻挡能力和高度稳定的薄膜状态的优异特性的有机化合物。本发明的化合物是具有三苯基胺结构的芳基胺化合物。芳族胺化合物在有机电致发光器件中用作至少一种有机层的构成材料，该有机电致发光器件包括一对电极和夹在该对电极之间的一个或多个有机层。

23. 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。

24. 发明申请

US20100090588A1 COMPOUND HAVING TRIAZINE RING STRUCTURE SUBSTITUTED WITH PYRIDYL GROUP AND ORGANIC ELECTROLUMINESCENT DEVICE 审中-公开
标题翻译：用吡啶基和有机电致发光器件取代的TRIAZINE环结构的化合物
公开(公告)号：US20100090588A1
公开(公告)日：2010-04-15
申请号：US12438207
申请日：2007-08-16
申请人： Norimasa Yokoyama , Toru Akisada , Makoto Nagaoka , Yoshio Taniguchi , Musubu Ichikawa
发明人： Norimasa Yokoyama , Toru Akisada , Makoto Nagaoka , Yoshio Taniguchi , Musubu Ichikawa
IPC分类号： H01J1/63 , C07D401/14
CPC分类号： H01L51/0067 , C07D401/14 , C07D417/14 , C09K11/06 , C09K2211/1011 , C09K2211/1029 , C09K2211/1059 , C09K2211/1092 , H01L51/0052 , H01L51/0071 , H01L51/0072 , H01L51/0081 , H01L51/5012 , H01L51/5048 , H01L51/5092 , H01L51/5096 , H01L2251/308 , H05B33/14 , H05B33/22
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 using the compound. The invention relates to a compound having a triazine ring structure having pyridyl groups 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 the compound is used as a constituent material of at least one of the organic layer(s): 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 R8 may be the same or different from one another and each independently represents a hydrogen atom, a fluorine atom, a trifluoromethyl group, a cyano group, an alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.
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，并提供一种使用该化合物具有高效率和高耐久性的有机EL器件。本发明涉及由通式（1）表示的具有连接有吡啶基的三嗪环结构的化合物; 以及包含一对电极和介于电极之间的至少一个有机层的有机电致发光器件，其中所述化合物用作至少一个有机层的构成材料：其中Ar表示取代或未取代的芳香族烃基，取代或未取代的芳香族杂环基，或取代或未取代的稠合多环芳香族基; R 1〜R 8可以相同也可以不同，各自独立地表示氢原子，氟原子，三氟甲基，氰基，烷基，取代或未取代的芳香族烃基，取代或未取代的芳香族杂环基团或取代或未取代的稠合多环芳基。

25. 发明授权

US09564600B2 Compound having an indolocarbazole ring structure and organic electroluminescent device 有权
标题翻译：具有吲哚咔唑环结构的化合物和有机电致发光器件
公开(公告)号：US09564600B2
公开(公告)日：2017-02-07
申请号：US14000406
申请日：2012-02-14
申请人： Norimasa Yokoyama , Makoto Nagaoka , Sawa Izumi , Hiroshi Ookuma , Shuichi Hayashi
发明人： Norimasa Yokoyama , Makoto Nagaoka , Sawa Izumi , Hiroshi Ookuma , Shuichi Hayashi
IPC分类号： H01L51/00 , C07D487/04 , C09K11/06 , H05B33/10 , H01L51/50
CPC分类号： H01L51/006 , C07D487/04 , C09K11/06 , C09K2211/1007 , C09K2211/1011 , C09K2211/1014 , C09K2211/1029 , C09K2211/1037 , C09K2211/1088 , C09K2211/1092 , H01L51/0061 , H01L51/0067 , H01L51/0071 , H01L51/0072 , H01L51/0073 , H01L51/5056 , H05B33/10
摘要： A compound having an indolocarbazole ring structure is represented by the following general formula (1), and is used as a material for forming a highly efficient and highly durable organic electroluminescent device. The compound features excellent hole injection/transport capability, has electron blocking power and is highly stable in the form of a thin film. wherein, A is a divalent aromatic hydrocarbon group or aromatic heterocyclic group, Ar1 to Ar4 are monovalent aromatic hydrocarbon groups or aromatic heterocyclic groups, and R1 to R9 are hydrogen atoms, deuterium atoms, fluorine atoms, chlorine atoms, cyano groups, nitro groups, alkyl groups, cycloalkyl groups, alkenyl groups, alkyloxy groups, cycloalkyloxy groups, aromatic hydrocarbon groups, aromatic heterocyclic groups or aryloxy groups.
摘要翻译：具有吲哚咔唑环结构的化合物由以下通式（1）表示，用作形成高效耐用的有机电致发光器件的材料。该化合物具有优异的空穴注入/输送能力，具有电子阻挡能力，并且以薄膜的形式高度稳定。其中，A为二价芳香族烃基或芳香族杂环基，Ar 1〜Ar 4为1价芳香族烃基或芳香族杂环基，R 1〜R 9为氢原子，氘原子，氟原子，氯原子，氰基硝基，烷基，环烷基，烯基，烷氧基，环烷氧基，芳族烃基，芳族杂环基或芳氧基。

26. 发明申请

US20110257404A1 METHOD OF PRODUCING AROMATIC AMINO COMPOUNDS 有权
标题翻译：生产芳族氨基化合物的方法
公开(公告)号：US20110257404A1
公开(公告)日：2011-10-20
申请号：US13123098
申请日：2010-01-25
申请人： Norimasa Yokoyama , Makoto Nagaoka , Kazunori Togashi
发明人： Norimasa Yokoyama , Makoto Nagaoka , Kazunori Togashi
IPC分类号： C07D401/14 , C07D209/82 , C07C65/03 , C07C213/08
CPC分类号： C07D209/86 , C07C209/10 , C07C2603/18 , C07D249/08 , C07D401/14 , C07C211/55
摘要： [Problem] To provide a method of producing an aromatic amino compound by using a primary or secondary amine compound and a halogenated aromatic compound as starting materials, and relying upon the Ullmann reaction, the method being capable of obtaining the highly pure aromatic amino compound in high yields and inexpensively.[Means for Solution] A method of producing an aromatic amino compound by using a primary or secondary amine compound having an aromatic ring group and a halogenated aromatic compound as starting materials, reacting the amine compound with the halogenated aromatic compound in the presence of a copper catalyst and a base so as to produce the aromatic amino compound having a structure in which an aromatic ring group derived from the halogenated aromatic compound is coupled to the amino group of the amine compound, wherein the amine compound and the halogenated aromatic compound are reacted together under a condition where an aromatic oxycarboxylic acid having a hydroxyl group and a hydroxycarbonyl group that are bonded to neighboring carbon atoms, is made present together with the copper catalyst and the base.
摘要翻译： [问题]为了提供通过使用伯胺或仲胺化合物和卤代芳族化合物作为原料制备芳香族氨基化合物的方法，依赖于乌尔曼反应，该方法能够获得高纯度芳香族氨基化合物产量高，成本低廉。 [解决方案]通过使用具有芳环基和卤代芳族化合物的伯胺或仲胺化合物作为起始原料制备芳族氨基化合物的方法，使胺化合物与卤代芳族化合物在铜的存在下反应催化剂和碱，以产生具有这样一种结构的芳族氨基化合物，其中衍生自卤代芳族化合物的芳族环基团与胺化合物的氨基偶合，其中胺化合物和卤代芳族化合物一起反应在具有与相邻碳原子键合的羟基和羟基羰基的芳族羟基羧酸的情况下，与铜催化剂和碱一起存在。

27. 发明申请

US20110001129A1 SUBSTITUTED BIPYRIDYL COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE 有权
标题翻译：取代的双嘧啶化合物和有机电致发光器件
公开(公告)号：US20110001129A1
公开(公告)日：2011-01-06
申请号：US12735885
申请日：2009-02-25
申请人： Norimasa Yokoyama , Shuichi Hayashi , Makoto Nagaoka , Yoshio Taniguchi , Musubu Ichikawa
发明人： Norimasa Yokoyama , Shuichi Hayashi , Makoto Nagaoka , Yoshio Taniguchi , Musubu Ichikawa
IPC分类号： H01L51/50 , C07D401/14 , C07D403/14 , C07D471/04
CPC分类号： H01L51/0067 , C07D213/22 , C09K11/06 , C09K2211/1007 , C09K2211/1011 , C09K2211/1029 , C09K2211/1059 , H01L51/0085 , H05B33/10
摘要： [Problem] To provide an organic compound which shows an excellent electron-injecting/transporting performance, has a hole-blocking ability and shows a high stability as a film, that is, having excellent characteristics as a material for organic electroluminescent device having high efficiency and high durability; and to provide an organic EL device comprising the compound and having high efficiency and high durability.[Means for Solution] A substituted bipyridyl compound represented by the general formula (1); and an organic electroluminescent device comprising a pair of electrodes and at least one organic layer sandwiched between then, wherein the compound is used as the constitutive material of at least one organic layer. (wherein R1 to R7 may be the same or different, each representing 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; n indicates an integer of from 2 to 4; A represents a di- to tetra-valent, substituted or unsubstituted aromatic hydrocarbon group, a di- to tetra-valent, substituted or unsubstituted aromatic heterocyclic group, 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 n=2, the two bipyridyl structures may direct bond to each other, and in the case, A is absent).
摘要翻译：为了提供一种显示出优异的电子注入/传输性能的有机化合物，具有空穴阻挡能力并且显示出作为膜的高稳定性，即作为高效率的有机电致发光器件的材料具有优异的特性耐用性高; 并且提供包含该化合物并具有高效率和高耐久性的有机EL器件。 [解决方案]由通式（1）表示的取代的联吡啶基化合物; 以及包括一对电极和夹在之间的至少一个有机层的有机电致发光器件，其中所述化合物用作至少一个有机层的组成材料。（其中R 1至R 7可以相同或不同，各自表示氢原子，氟原子，氯原子，氰基，三氟甲基，具有1至6个碳原子的直链或支链烷基，取代的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2〜4的整数，A表示二价至四价的取代或未取代的芳香族烃基，二价至四元，取代或未取代的芳族杂环基，二价至四价，取代或未取代的稠合多环芳族基团或由以下通式（2）表示的三价基团：（其中X， Y和Z各自表示碳原子或氮原子）;条件是当n = 2时，两个联吡啶基结构可以彼此直接键合，在此情况下，A不存在）。

28. 发明授权

US08735626B2 Method of producing aromatic amino compounds 有权
标题翻译：制备芳香族氨基化合物的方法
公开(公告)号：US08735626B2
公开(公告)日：2014-05-27
申请号：US13123098
申请日：2010-01-25
申请人： Norimasa Yokoyama , Makoto Nagaoka , Kazunori Togashi
发明人： Norimasa Yokoyama , Makoto Nagaoka , Kazunori Togashi
IPC分类号： C07C211/00 , C07C59/00 , C07C65/21
CPC分类号： C07D209/86 , C07C209/10 , C07C2603/18 , C07D249/08 , C07D401/14 , C07C211/55
摘要： A method of producing an aromatic amino compound using a primary or secondary amine compound and a halogenated aromatic compound as starting materials, and relying upon the Ullmann reaction, the method being capable of obtaining the highly pure aromatic amino compound in high yields and inexpensively. A primary or secondary amine compound having an aromatic ring group and a halogenated aromatic compound as starting materials, are reacted with the halogenated aromatic compound in the presence of copper catalyst and base to produce the aromatic amino compound having a structure in which an aromatic ring group derived from the halogenated aromatic compound is coupled to the amino group of the amine compound, wherein the amine compound and the halogenated aromatic compound are reacted together such that an aromatic oxycarboxylic acid having a hydroxyl group and a hydroxycarbonyl group bonded to neighboring carbon atoms, is present together with the copper catalyst and the base.
摘要翻译：使用伯胺或仲胺化合物和卤代芳族化合物作为原料制备芳香族氨基化合物的方法，依赖乌尔曼反应，该方法能够以高收率和低成本获得高纯度芳香族氨基化合物。具有芳环基团和卤代芳族化合物作为起始原料的伯胺或仲胺化合物与卤化芳族化合物在铜催化剂和碱存在下反应，生成具有芳环基团的芳族氨基化合物来自卤代芳香族化合物的胺化合物的氨基与胺化合物的氨基偶联，其中胺化合物和卤代芳香族化合物反应，使得具有与相邻碳原子键合的羟基和羟基羰基的芳族羟基羧酸为与铜催化剂和碱一起存在。

29. 发明申请

US20140124756A1 COMPOUND HAVING AN INDOLOCARBAZOLE RING STRUCTURE AND ORGANIC ELECTROLUMINESCENT DEVICE 有权
标题翻译：具有吲哚卡扎环结构和有机电致发光器件的化合物
公开(公告)号：US20140124756A1
公开(公告)日：2014-05-08
申请号：US14000406
申请日：2012-02-14
申请人： Norimasa Yokoyama , Makoto Nagaoka , Sawa Izumi , Hiroshi Ookuma , Shuichi Hayashi
发明人： Norimasa Yokoyama , Makoto Nagaoka , Sawa Izumi , Hiroshi Ookuma , Shuichi Hayashi
IPC分类号： H01L51/00
CPC分类号： H01L51/006 , C07D487/04 , C09K11/06 , C09K2211/1007 , C09K2211/1011 , C09K2211/1014 , C09K2211/1029 , C09K2211/1037 , C09K2211/1088 , C09K2211/1092 , H01L51/0061 , H01L51/0067 , H01L51/0071 , H01L51/0072 , H01L51/0073 , H01L51/5056 , H05B33/10
摘要： A compound having an indolocarbazole ring structure is represented by the following general formula (1), and is used as a material for forming a highly efficient and highly durable organic electroluminescent device. The compound features excellent hole injection/transport capability, has electron blocking power and is highly stable in the form of a thin film. wherein, A is a divalent aromatic hydrocarbon group or aromatic heterocyclic group, Ar1 to Ar4 are monovalent aromatic hydrocarbon groups or aromatic heterocyclic groups, and R1 to R9 are hydrogen atoms, deuterium atoms, fluorine atoms, chlorine atoms, cyano groups, nitro groups, alkyl groups, cycloalkyl groups, alkenyl groups, alkyloxy groups, cycloalkyloxy groups, aromatic hydrocarbon groups, aromatic heterocyclic groups or aryloxy groups.
摘要翻译：具有吲哚咔唑环结构的化合物由以下通式（1）表示，用作形成高效耐用的有机电致发光器件的材料。该化合物具有优异的空穴注入/输送能力，具有电子阻挡能力，并且以薄膜的形式高度稳定。其中，A为二价芳香族烃基或芳香族杂环基，Ar 1〜Ar 4为一价芳香族烃基或芳香族杂环基，R 1〜R 9为氢原子，氘原子，氟原子，氯原子，氰基，硝基，烷基，环烷基，烯基，烷氧基，环烷氧基，芳族烃基，芳族杂环基或芳氧基。

30. 发明授权

US09196839B2 Compound having triphenylamine structure, and organic electroluminescent device 有权
标题翻译：具有三苯胺结构的化合物和有机电致发光器件
公开(公告)号：US09196839B2
公开(公告)日：2015-11-24
申请号：US13574923
申请日：2011-01-25
申请人： Norimasa Yokoyama , Makoto Nagaoka , Kouki Kase , Shingo Ozawa , Shigeru Kusano
发明人： Norimasa Yokoyama , Makoto Nagaoka , Kouki Kase , Shingo Ozawa , Shigeru Kusano
IPC分类号： H01L51/50 , H01L51/00 , C07C211/54 , C07C211/56 , C07D209/86 , C09K11/06
CPC分类号： H01L51/0059 , C07B2200/05 , C07C211/54 , C07C211/56 , C07C2603/18 , C07D209/86 , C09K11/06 , C09K2211/1014 , H01L51/5048 , H01L51/5088 , H01L51/5096
摘要： There is provided an organic compound of excellent characteristics that exhibits excellent hole-injecting/transporting performance and has an electron blocking ability and a highly stable thin-film state with excellent heat resistance. The compound of the present invention is an arylamine compound having a triphenylamine structure. The arylamine compound is used as a constituent material of at least one organic layer in an organic electroluminescent device that includes a pair of electrodes, and one or more organic layers sandwiched between the pair of electrodes.
摘要翻译：提供具有优异的空穴注入/输送性能，具有优异的耐热性的电子阻挡能力和高度稳定的薄膜状态的优异特性的有机化合物。本发明的化合物是具有三苯基胺结构的芳基胺化合物。芳族胺化合物在有机电致发光器件中用作至少一种有机层的构成材料，该有机电致发光器件包括一对电极和夹在该对电极之间的一个或多个有机层。

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