公开(公告)号：US20050090692A1

公开(公告)日：2005-04-28

申请号：US10508910

申请日：2003-03-26

申请人： Nobutaka Akashi ,  Hideki Norisada ,  Tomoko Hayashi ,  Yasuhiko Shirota

发明人： Nobutaka Akashi ,  Hideki Norisada ,  Tomoko Hayashi ,  Yasuhiko Shirota

IPC分类号： C07C211/54 ,  C07C211/58 ,  C07C211/61 ,  G03G5/06 ,  C07C211/00

CPC分类号： C07C211/54 ,  C07C211/58 ,  C07C211/61 ,  G03G5/0614 ,  Y10S428/917

摘要： The invention provides 1,3,5-tris(arylamino)benzenes represented by the general formula (I) wherein A is naphthyl, anthryl, phenanthryl, biphenylyl or terphenylyl group, and R is alkyl having 1-6 carbon atoms or cycloalkyl group having five or six carbon atoms. The 1,3,5-tris(arylamino)benzenes have oxidation potentials in the range of about 0.5-0.6V, excellent reversibility in oxidation-reduction process and high glass transition temperatures and in addition, they are capable of forming stable and durable amorphous film useful as high performance organic semiconductors at normal temperatures or higher with no aid of binder resins, that is, by themselves.

摘要翻译： 本发明提供由通式（I）表示的1,3,5-三（芳氨基）苯，其中A为萘基，蒽基，菲基，联苯基或三联苯基，R为具有1-6个碳原子的烷基或具有 五或六个碳原子。 1,3,5-三（芳基氨基）苯具有在约0.5-0.6V的范围内的氧化电位，氧化还原过程的优异的可逆性和高的玻璃化转变温度，此外，它们能够形成稳定和耐用的无定形 膜在正常温度或更高温度下作为高性能有机半导体，无助于粘合剂树脂，也就是本身。

公开(公告)号：US07196224B2

公开(公告)日：2007-03-27

申请号：US10508910

申请日：2003-03-26

申请人： Nobutaka Akashi ,  Hideki Norisada ,  Tomoko Hayashi ,  Yasuhiko Shirota

发明人： Nobutaka Akashi ,  Hideki Norisada ,  Tomoko Hayashi ,  Yasuhiko Shirota

IPC分类号： C07C211/61 ,  C07C211/58 ,  C07C211/55 ,  G03G15/06

CPC分类号： C07C211/54 ,  C07C211/58 ,  C07C211/61 ,  G03G5/0614 ,  Y10S428/917

摘要： The invention provides 1,3,5-tris(arylamino)benzenes represented by the general formula (I) wherein A is naphthyl, anthryl, phenanthryl, biphenylyl or terphenylyl group, and R is alkyl having 1–6 carbon atoms or cycloalkyl group having five or six carbon atoms. The 1,3,5-tris(arylamino)benzenes have oxidation potentials in the range of about 0.5–0.6V, excellent reversibility in oxidation-reduction process and high glass transition temperatures and in addition, they are capable of forming stable and durable amorphous film useful as high performance organic semiconductors at normal temperatures or higher with no aid of binder resins, that is, by themselves.

摘要翻译： 本发明提供由通式（I）表示的1,3,5-三（芳基氨基）苯，

公开(公告)号：US20090066222A1

公开(公告)日：2009-03-12

申请号：US11667134

申请日：2005-10-31

申请人： Nobutaka Akashi ,  Kaori Inayama ,  Hiroshi Inada ,  Yasuhiko Shirota

发明人： Nobutaka Akashi ,  Kaori Inayama ,  Hiroshi Inada ,  Yasuhiko Shirota

IPC分类号： H01L51/05 ,  C07C211/53 ,  H01J1/63

CPC分类号： H01L51/0059 ,  C07C211/54 ,  H01L51/0081 ,  H01L51/5048 ,  H01L2251/308 ,  H05B33/22

摘要： The invention provides an organic electronic functional material which comprises a 1,3,5-tris(4-(N,N-diarylamino)phenyl)benzene represented by the general formula (I) wherein A and B are each preferably a phenyl group having an alkyl group of 1-6 carbons or a cycloalkyl group of 5 or 6 carbons at the 4-position.

摘要翻译： 本发明提供一种有机电子功能材料，其包含由通式（I）表示的1,3,5-三（4-（N，N-二芳基氨基）苯基）苯，其中A和B各自优选为具有 4-位的1-6个碳的烷基或5或6个碳的环烷基。

公开(公告)号：US20070066848A1

公开(公告)日：2007-03-22

申请号：US10580052

申请日：2004-11-17

申请人： Nobutaka Akashi ,  Yasuhiko Shirota

发明人： Nobutaka Akashi ,  Yasuhiko Shirota

IPC分类号： C07C211/54 ,  H01L51/54

CPC分类号： H01L51/0059 ,  H01L51/0081 ,  H01L51/5048 ,  H01L51/5088 ,  H01L2251/308 ,  Y10S428/917

摘要： The invention provides an organo-electronic functional material comprising a tris(arylamino)benzene represented by the general formula (I) wherein A and B are each a group represented by the general formula (II) in which R is an alkyl group of 1-6 carbons or a cycloalkyl group of 5 or 6 carbon atoms and n is 0, 1, 2 or 3, and A and B may be the same or different from each other, and exhibiting a cyclic voltamogram in which a deviation of peak current of cyclic curves as measured 50 times at a sweep rate of 20 mV/s falls within ±10% of the average of peak current. The organo-electronic functional material has an opto-electronic exchanging function, a reversible oxidation-reduction property and a high glass transition temperature, and can form amorphous film in itself. In addition, it is stable and exhibits only slight variation of peak current in repeated oxidation-reduction process so that it is suitable for use as, for example, a hole transporting material among others in various electronic devices including an organic electroluminescence element.

摘要翻译： 本发明提供一种有机电子功能材料，其包含由通式（I）表示的三（芳基氨基）苯，其中A和B各自为通式（II）表示的基团，其中R为1- 6个碳原子或5或6个碳原子的环烷基，n为0,1,2或3，A和B可以相同或不同，表现出循环伏安图，其中峰电流的偏差 以20mV / s的扫描速率测量50次的循环曲线落在峰值电流平均值的±10％以内。 有机电子功能材料具有光电交换功能，可逆氧化还原性和高玻璃化转变温度，并且可以自身形成非晶膜。 此外，它是稳定的，并且在重复氧化还原处理中仅表现出微小的峰值电流变化，因此其适合用作例如包括有机电致发光元件在内的各种电子器件中的空穴传输材料。

公开(公告)号：US07629059B2

公开(公告)日：2009-12-08

申请号：US10580052

申请日：2004-11-17

申请人： Nobutaka Akashi ,  Yasuhiko Shirota

发明人： Nobutaka Akashi ,  Yasuhiko Shirota

IPC分类号： H01L51/54 ,  C07C211/54

CPC分类号： H01L51/0059 ,  H01L51/0081 ,  H01L51/5048 ,  H01L51/5088 ,  H01L2251/308 ,  Y10S428/917

摘要： The invention provides an organo-electronic functional material comprising a tris(arylamino)benzene represented by the general formula (I) wherein A and B are each a group represented by the general formula (II) in which R is an alkyl group of 1-6 carbons or a cycloalkyl group of 5 or 6 carbon atoms and n is 0, 1, 2 or 3, and A and B may be the same or different from each other, and exhibiting a cyclic voltamogram in which a deviation of peak current of cyclic curves as measured 50 times at a sweep rate of 20 mV/s falls within ±10% of the average of peak current. The organo-electronic functional material has an opto-electronic exchanging function, a reversible oxidation-reduction property and a high glass transition temperature, and can form amorphous film in itself. In addition, it is stable and exhibits only slight variation of peak current in repeated oxidation-reduction process so that it is suitable for use as, for example, a hole transporting material among others in various electronic devices including an organic electroluminescence element.

摘要翻译： 本发明提供一种有机电子功能材料，其包含由通式（I）表示的三（芳基氨基）苯，其中A和B各自为通式（II）表示的基团，其中R为1- 6个碳原子或5或6个碳原子的环烷基，n为0,1,2或3，A和B可以相同或不同，表现出循环伏安图，其中峰电流的偏差 以20mV / s的扫描速率测量50次的循环曲线落在峰值电流平均值的±10％以内。 有机电子功能材料具有光电交换功能，可逆氧化还原性和高玻璃化转变温度，并且可以自身形成非晶膜。 此外，它是稳定的，并且在重复氧化还原处理中仅表现出微小的峰值电流变化，因此其适合用作例如包括有机电致发光元件在内的各种电子器件中的空穴传输材料。

公开(公告)号：US07271291B2

公开(公告)日：2007-09-18

申请号：US10549166

申请日：2004-03-15

申请人： Hiroshi Inada ,  Nobutaka Akashi ,  Tomoko Hayashi

发明人： Hiroshi Inada ,  Nobutaka Akashi ,  Tomoko Hayashi

IPC分类号： C07C211/54 ,  H01L35/24

CPC分类号： C07C211/58 ,  H01L51/0059 ,  H01L51/006 ,  H01L51/5048

摘要： The invention provides 1,3,5-tris(arylamino)benzenes represented by the general formula (I) wherein A is naphthyl, anthryl or phenanthryl group, and R is hydrogen atom or diarylamino group. These 1,3,5-tris(arylamino)benzenes have oxidation potentials in the range of about 0.5-0.6V, excellent reversibility in oxidation-reduction process, high glass transition temperatures and high heat resistance, so that they can form practicable organic semiconductor film readily by a coating method or a vacuum deposition method. In addition, they are capable of forming stable and durable amorphous film useful as high performance organic semiconductors at normal temperatures or higher with no aid of binder resins, that is, by themselves.

摘要翻译： 本发明提供由通式（I）表示的1,3,5-三（芳氨基）苯，其中A为萘基，蒽基或菲基，R为氢原子或二芳基氨基。 这些1,3,5-三（芳基氨基）苯具有在约0.5-0.6V的范围内的氧化电位，氧化还原过程的优异可逆性，高玻璃化转变温度和高耐热性，使得它们可以形成可行的有机半导体 通过涂布方法或真空沉积方法容易地制备薄膜。 此外，它们能够在常温或更高温度下形成稳定且耐用的无定形薄膜，无需粘合剂树脂，即本身就可以使用。

公开(公告)号：US20060173216A1

公开(公告)日：2006-08-03

申请号：US10549166

申请日：2004-03-15

申请人： Hiroshi Inada ,  Nobutaka Akashi ,  Tomoko Hayashi

发明人： Hiroshi Inada ,  Nobutaka Akashi ,  Tomoko Hayashi

IPC分类号： C07C211/50

CPC分类号： C07C211/58 ,  H01L51/0059 ,  H01L51/006 ,  H01L51/5048

摘要： The invention provides 1,3,5-tris(arylamino)benzenes represented by the general formula (I) wherein A is naphthyl, anthryl or phenanthryl group, and R is hydrogen atom or diarylamino group. These 1,3,5-tris(arylamino)benzenes have oxidation potentials in the range of about 0.5-0.6V, excellent reversibility in oxidation-reduction process, high glass transition temperatures and high heat resistance, so that they can form practicable organic semiconductor film readily by a coating method or a vacuum deposition method. In addition, they are capable of forming stable and durable amorphous film useful as high performance organic semiconductors at normal temperatures or higher with no aid of binder resins, that is, by themselves.

摘要翻译： 本发明提供由通式（I）表示的1,3,5-三（芳氨基）苯，其中A为萘基，蒽基或菲基，R为氢原子或二芳基氨基。 这些1,3,5-三（芳基氨基）苯具有在约0.5-0.6V的范围内的氧化电位，氧化还原过程的优异可逆性，高玻璃化转变温度和高耐热性，使得它们可以形成可行的有机半导体 通过涂布方法或真空沉积方法容易地制备薄膜。 此外，它们能够在常温或更高温度下形成稳定且耐用的无定形薄膜，无需粘合剂树脂，即本身就可以使用。

公开(公告)号：US08043725B2

公开(公告)日：2011-10-25

申请号：US12376176

申请日：2007-07-20

申请人： Tomokazu Kobata ,  Nobutaka Akashi

发明人： Tomokazu Kobata ,  Nobutaka Akashi

IPC分类号： H01L51/54

CPC分类号： H01L51/0059 ,  H01L51/006 ,  H01L51/0072 ,  H01L51/0081 ,  H01L51/5048 ,  H01L51/5088 ,  H01L2251/308 ,  Y10S428/917

摘要： The invention provides an organic electroluminescence element which comprises a hole transporting layer which comprises a tris(p-terphenyl-4-yl)amine represented by the general formula (I) wherein R1, R2 and R3 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group which may have substituents or an aryl group which may have substituents as a hole transporting agent, and a hole injecting layer which comprises a hole injecting agent comprising an aromatic tertiary amine having an ionization potential in the range of 5.2-5.6 eV. This organic electroluminescence element can be driven at a low voltage with high efficiency and at high luminance.

摘要翻译： 本发明提供一种有机电致发光元件，其包含空穴传输层，其包含由通式（I）表示的三（对三联苯-4-基）胺，其中R 1，R 2和R 3各自独立地为氢原子，烷基 可以具有取代基的环烷基或可以具有取代基的芳基作为空穴传输剂，以及空穴注入层，其包含空穴注入剂，所述空穴注入剂包含电离电位在5.2-5.6范围内的芳香族叔胺 eV。 该有机电致发光元件可以以高效率和高亮度的低电压驱动。

公开(公告)号：US20100006828A1

公开(公告)日：2010-01-14

申请号：US12376176

申请日：2007-07-20

申请人： Tomokazu Kobata ,  Nobutaka Akashi

发明人： Tomokazu Kobata ,  Nobutaka Akashi

IPC分类号： H01L51/54

CPC分类号： H01L51/0059 ,  H01L51/006 ,  H01L51/0072 ,  H01L51/0081 ,  H01L51/5048 ,  H01L51/5088 ,  H01L2251/308 ,  Y10S428/917

摘要： The invention provides an organic electroluminescence element which comprises a hole transporting layer which comprises a tris(p-terphenyl-4-yl)amine represented by the general formula (I) wherein R1, R2 and R3 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group which may have substituents or an aryl group which may have substituents as a hole transporting agent, and a hole injecting layer which comprises a hole injecting agent comprising an aromatic tertiary amine having an ionization potential in the range of 5.2-5.6 eV. This organic electroluminescence element can be driven at a low voltage with high efficiency and at high luminance.

摘要翻译： 本发明提供一种有机电致发光元件，其包含空穴传输层，其包含由通式（I）表示的三（对三联苯-4-基）胺，其中R 1，R 2和R 3各自独立地为氢原子，烷基 可以具有取代基的环烷基或可以具有取代基的芳基作为空穴传输剂，以及空穴注入层，其包含空穴注入剂，所述空穴注入剂包含电离电位在5.2-5.6范围内的芳香族叔胺 eV。 该有机电致发光元件可以以高效率和高亮度的低电压驱动。

公开(公告)号：US20110186834A1

公开(公告)日：2011-08-04

申请号：US13062156

申请日：2009-08-28

申请人： Masashi Ohta ,  Nobutaka Akashi

发明人： Masashi Ohta ,  Nobutaka Akashi

IPC分类号： H01L51/54 ,  C07C211/54

CPC分类号： H01L51/0059 ,  C07C211/54 ,  H01L51/5048 ,  H01L51/5088

摘要： The invention provides a 1,3,5-tris(diarylamino)benzene represented by the general formula (I) in which R1 to R6 are each independently a group which is represented by the general formula (II) wherein R is independently a hydrogen atom, an alkyl group of 1 to 6 carbon atoms or a cycloalkyl group of 5 or 6 carbon atoms, m is 2, 3, 4 or 5, and n is 0, 1 or 2, provided that at least one of R1 to R6 is independently a group represented by the general formula (II) wherein R is an alkyl group of 1 to 6 carbon atoms or a cycloalkyl group of 5 or 6 carbon atoms, m is 2, 3, 4 or 5, and n is 0, 1 or 2.

摘要翻译： 本发明提供由通式（I）表示的1,3,5-三（二芳基氨基）苯，其中R 1至R 6各自独立地是由通式（II）表示的基团，其中R独立地为氢原子 ，1〜6个碳原子的烷基或5或6个碳原子的环烷基，m为2,3,4或5，n为0,1或2，条件是R 1至R 6中的至少一个为 独立地是由通式（II）表示的基团，其中R为1至6个碳原子的烷基或5或6个碳原子的环烷基，m为2,3,4或5，n为0,1 或2。