公开(公告)号：US08986858B2

公开(公告)日：2015-03-24

申请号：US13578942

申请日：2011-01-27

申请人： Masashi Tada ,  Junya Ogawa ,  Takahiro Kai ,  Megumi Matsumoto ,  Yasuhisa Tsutsumi

发明人： Masashi Tada ,  Junya Ogawa ,  Takahiro Kai ,  Megumi Matsumoto ,  Yasuhisa Tsutsumi

IPC分类号： H01L51/50 ,  C07D403/10 ,  C07D209/86 ,  C07D401/14 ,  C07D403/14 ,  C07D405/14 ,  C07D409/14 ,  H01L51/00

CPC分类号： C07D403/10 ,  C07D209/86 ,  C07D401/14 ,  C07D403/14 ,  C07D405/14 ,  C07D409/14 ,  H01L51/0067 ,  H01L51/0072 ,  H01L51/0073 ,  H01L51/0074 ,  H01L51/0087 ,  H01L51/5016 ,  H01L51/5048 ,  H01L51/5096 ,  Y10S428/917

摘要： Disclosed is an organic electroluminescent device (organic EL device) that is improved in luminous efficiency, sufficiently secures driving stability, and has a simple configuration. This organic EL device comprises organic layers between an anode and a cathode piled one upon another on a substrate and at least one organic layer selected from a light-emitting layer, a hole-transporting layer, an electron-transporting layer, and a hole-blocking layer contains a carbazole compound represented by the following formula (1). In the case where the light-emitting layer of the organic electroluminescent device contains a phosphorescent dopant and a host material, it is the carbazole compound that is contained as the host material. In formula (1), X is C—Y or a nitrogen atom; Y is a hydrogen atom, an alkyl group, a cycloalkyl group, or an aromatic group; n is an integer of 2 to 4: A is an n-valent aromatic group; L is a direct bond or a divalent aromatic group; and R is a hydrogen atom, an alkyl group, or a cycloalkyl group.

摘要翻译： 公开了一种提高发光效率的有机电致发光器件（有机EL器件），足够确保驱动稳定性，并且具有简单的结构。 该有机EL器件包括在基板上彼此堆叠的阳极和阴极之间的有机层以及从发光层，空穴传输层，电子传输层和空穴传输层中选择的至少一个有机层。 阻挡层含有由下式（1）表示的咔唑化合物。 在有机电致发光器件的发光层含有磷光掺杂剂和主体材料的情况下，作为主体材料含有咔唑化合物。 在式（1）中，X是C-Y或氮原子; Y是氢原子，烷基，环烷基或芳基; n为2〜4的整数：A为n价的芳香族基团; L是直接键或二价芳基; R为氢原子，烷基或环烷基。

公开(公告)号：US20120319095A1

公开(公告)日：2012-12-20

申请号：US13578942

申请日：2011-01-27

申请人： Masashi Tada ,  Junya Ogawa ,  Takahiro Kai ,  Megumi Matsumoto ,  Yasuhisa Tsutsumi

发明人： Masashi Tada ,  Junya Ogawa ,  Takahiro Kai ,  Megumi Matsumoto ,  Yasuhisa Tsutsumi

IPC分类号： H01L51/54

CPC分类号： C07D403/10 ,  C07D209/86 ,  C07D401/14 ,  C07D403/14 ,  C07D405/14 ,  C07D409/14 ,  H01L51/0067 ,  H01L51/0072 ,  H01L51/0073 ,  H01L51/0074 ,  H01L51/0087 ,  H01L51/5016 ,  H01L51/5048 ,  H01L51/5096 ,  Y10S428/917

摘要： Disclosed is an organic electroluminescent device (organic EL device) that is improved in luminous efficiency, sufficiently secures driving stability, and has a simple configuration. This organic EL device comprises organic layers between an anode and a cathode piled one upon another on a substrate and at least one organic layer selected from a light-emitting layer, a hole-transporting layer, an electron-transporting layer, and a hole-blocking layer contains a carbazole compound represented by the following formula (1). In the case where the light-emitting layer of the organic electroluminescent device contains a phosphorescent dopant and a host material, it is the carbazole compound that is contained as the host material. In formula (1), X is C—Y or a nitrogen atom; Y is a hydrogen atom, an alkyl group, a cycloalkyl group, or an aromatic group; n is an integer of 2 to 4: A is an n-valent aromatic group; L is a direct bond or a divalent aromatic group; and R is a hydrogen atom, an alkyl group, or a cycloalkyl group.

摘要翻译： 公开了一种提高发光效率的有机电致发光器件（有机EL器件），足够确保驱动稳定性，并且具有简单的结构。 该有机EL器件包括在基板上彼此堆叠的阳极和阴极之间的有机层以及从发光层，空穴传输层，电子传输层和空穴传输层中选择的至少一个有机层。 阻挡层含有由下式（1）表示的咔唑化合物。 在有机电致发光器件的发光层含有磷光掺杂剂和主体材料的情况下，作为主体材料含有咔唑化合物。 在式（1）中，X是C-Y或氮原子; Y是氢原子，烷基，环烷基或芳基; n为2〜4的整数：A为n价的芳香族基团; L是直接键或二价芳基; R为氢原子，烷基或环烷基。

公开(公告)号：US09461250B2

公开(公告)日：2016-10-04

申请号：US13514047

申请日：2010-12-21

申请人： Junya Ogawa ,  Takahiro Kai ,  Toshihiro Yamamoto ,  Megumi Matsumoto

发明人： Junya Ogawa ,  Takahiro Kai ,  Toshihiro Yamamoto ,  Megumi Matsumoto

IPC分类号： H01L51/50 ,  H01L51/00 ,  C07D209/86 ,  C07D209/88 ,  C07D409/14 ,  C09K11/06

CPC分类号： H01L51/0072 ,  C07D209/86 ,  C07D209/88 ,  C07D409/14 ,  C09K11/06 ,  C09K2211/1029 ,  C09K2211/1088 ,  C09K2211/1092 ,  H01L51/0074 ,  H01L51/0085 ,  H01L51/5016

摘要： Disclosed is an organic electroluminescent device (organic EL device) which is improved in luminous efficiency, sufficiently secures driving stability, and has a simple configuration. The organic EL device of this invention comprises a light-emitting layer between an anode and a cathode piled one upon another on a substrate wherein the light-emitting layer contains a phosphorescent dopant and a 1,9-substituted carbazole compound as a host material. An example of the 1,9-substituted carbazole compound is represented by the following general formula (1). In formula (1), Ar is an aromatic hydrocarbon group or aromatic heterocyclic group; L is an aromatic hydrocarbon group or aromatic heterocyclic group; each of R1 to R3 is a hydrogen atom, an alkyl group, a cycloalkyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group; n is an integer of 1 to 3.

摘要翻译： 公开了一种提高发光效率的有机电致发光器件（有机EL器件），足够确保驱动稳定性，并且具有简单的结构。 本发明的有机EL器件包括在基板上彼此堆叠的阳极和阴极之间的发光层，其中发光层含有磷光掺杂剂和作为主体材料的1,9-取代的咔唑化合物。 1,9-取代的咔唑化合物的实例由以下通式（1）表示。 式（1）中，Ar为芳香族烃基或芳香族杂环基， L是芳族烃基或芳族杂环基; R 1〜R 3各自为氢原子，烷基，环烷基，芳香族烃基或芳香族杂环基; n为1〜3的整数。

公开(公告)号：US09337432B2

公开(公告)日：2016-05-10

申请号：US13990511

申请日：2011-11-28

申请人： Junya Ogawa ,  Takahiro Kai ,  Megumi Matsumoto

发明人： Junya Ogawa ,  Takahiro Kai ,  Megumi Matsumoto

IPC分类号： H01L51/50 ,  H01L51/00 ,  C07D209/82 ,  C07D401/04 ,  C07D403/04 ,  C07D405/04 ,  C07D409/04 ,  C09K11/06 ,  H05B33/14

CPC分类号： H01L51/0072 ,  C07D209/82 ,  C07D401/04 ,  C07D403/04 ,  C07D405/04 ,  C07D409/04 ,  C09K11/06 ,  C09K2211/1011 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/1059 ,  C09K2211/1088 ,  C09K2211/1092 ,  H01L51/0071 ,  H01L51/0073 ,  H01L51/5012 ,  H01L51/5056 ,  H01L51/5096 ,  H05B33/14

摘要： Provided is an organic electroluminescent device (organic EL device) which exhibits improved luminous efficiency, ensures sufficient driving stability, and has a simple configuration. The organic electroluminescent element includes an anode, a plurality of organic layers, and a cathode laminated on a substrate, and contains a carbazole compound represented by the general formula (1) in at least one layer selected from the group consisting of a emitting layer, a hole-transporting layer, and an electron-blocking layer. In general formula (1), L represents an m-valent aromatic hydrocarbon group or aromatic heterocyclic group, R's each represent hydrogen, an alkyl group, or a cycloalkyl group, m represents an integer of 1 to 3, and n's each represent an integer of 1 to 4, provided that at least one n represents an integer of 2 to 4, and at least one specific structure represented by the formula (1a) is present in the formula.

摘要翻译： 提供了一种有机电致发光器件（有机EL器件），其具有改善的发光效率，确保足够的驱动稳定性，并且具有简单的构造。 有机电致发光元件包括阳极，多个有机层和层叠在基板上的阴极，并且含有由通式（1）表示的咔唑化合物在至少一层中选自发光层， 空穴传输层和电子阻挡层。 通式（1）中，L表示1价的芳香族烃基或芳香族杂环基，R 3表示氢，烷基或环烷基，m表示1〜3的整数，n表示整数 1至4，条件是至少一个n表示2至4的整数，并且式中存在至少一个由式（1a）表示的具体结构。

公开(公告)号：US20130248845A1

公开(公告)日：2013-09-26

申请号：US13990511

申请日：2011-11-28

申请人： Junya Ogawa ,  Takahiro Kai ,  Megumi Matsumoto

发明人： Junya Ogawa ,  Takahiro Kai ,  Megumi Matsumoto

IPC分类号： H01L51/00

CPC分类号： H01L51/0072 ,  C07D209/82 ,  C07D401/04 ,  C07D403/04 ,  C07D405/04 ,  C07D409/04 ,  C09K11/06 ,  C09K2211/1011 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/1059 ,  C09K2211/1088 ,  C09K2211/1092 ,  H01L51/0071 ,  H01L51/0073 ,  H01L51/5012 ,  H01L51/5056 ,  H01L51/5096 ,  H05B33/14

摘要： Provided is an organic electroluminescent device (organic EL device) which exhibits improved luminous efficiency, ensures sufficient driving stability, and has a simple configuration. The organic electroluminescent element includes an anode, a plurality of organic layers, and a cathode laminated on a substrate, and contains a carbazole compound represented by the general formula (1) in at least one layer selected from the group consisting of a emitting layer, a hole-transporting layer, and an electron-blocking layer. In general formula (1), L represents an m-valent aromatic hydrocarbon group or aromatic heterocyclic group, R's each represent hydrogen, an alkyl group, or a cycloalkyl group, m represents an integer of 1 to 3, and n's each represent an integer of 1 to 4, provided that at least one n represents an integer of 2 to 4, and at least one specific structure represented by the formula (1a) is present in the formula.

摘要翻译： 提供了一种有机电致发光器件（有机EL器件），其具有改善的发光效率，确保足够的驱动稳定性，并且具有简单的构造。 有机电致发光元件包括阳极，多个有机层和层叠在基板上的阴极，并且含有由通式（1）表示的咔唑化合物在至少一层中选自发光层， 空穴传输层和电子阻挡层。 通式（1）中，L表示1价的芳香族烃基或芳香族杂环基，R 3表示氢，烷基或环烷基，m表示1〜3的整数，n表示整数 1至4，条件是至少一个n表示2至4的整数，并且式中存在至少一个由式（1a）表示的具体结构。

公开(公告)号：US20120235136A1

公开(公告)日：2012-09-20

申请号：US13514047

申请日：2010-12-21

申请人： Junya Ogawa ,  Takahiro Kai ,  Toshihiro Yamamoto ,  Megumi Matsumoto

发明人： Junya Ogawa ,  Takahiro Kai ,  Toshihiro Yamamoto ,  Megumi Matsumoto

IPC分类号： H01L51/50

CPC分类号： H01L51/0072 ,  C07D209/86 ,  C07D209/88 ,  C07D409/14 ,  C09K11/06 ,  C09K2211/1029 ,  C09K2211/1088 ,  C09K2211/1092 ,  H01L51/0074 ,  H01L51/0085 ,  H01L51/5016

摘要： Disclosed is an organic electroluminescent device (organic EL device) which is improved in luminous efficiency, sufficiently secures driving stability, and has a simple configuration. The organic EL device of this invention comprises a light-emitting layer between an anode and a cathode piled one upon another on a substrate wherein the light-emitting layer contains a phosphorescent dopant and a 1,9-substituted carbazole compound as a host material. An example of the 1,9-substituted carbazole compound is represented by the following general formula (1). In formula (1), Ar is an aromatic hydrocarbon group or aromatic heterocyclic group; L is an aromatic hydrocarbon group or aromatic heterocyclic group; each of R1 to R3 is a hydrogen atom, an alkyl group, a cycloalkyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group; n is an integer of 1 to 3.

摘要翻译： 公开了一种提高发光效率的有机电致发光器件（有机EL器件），足够确保驱动稳定性，并且具有简单的结构。 本发明的有机EL器件包括在基板上彼此堆叠的阳极和阴极之间的发光层，其中发光层含有磷光掺杂剂和作为主体材料的1,9-取代的咔唑化合物。 1,9-取代的咔唑化合物的实例由以下通式（1）表示。 式（1）中，Ar为芳香族烃基或芳香族杂环基， L是芳族烃基或芳族杂环基; R 1〜R 3各自为氢原子，烷基，环烷基，芳香族烃基或芳香族杂环基; n为1〜3的整数。

公开(公告)号：US20120305904A1

公开(公告)日：2012-12-06

申请号：US13578207

申请日：2011-02-07

申请人： Takahiro Kai ,  Masaki Komori ,  Toshihiro Yamamoto ,  Megumi Matsumoto

发明人： Takahiro Kai ,  Masaki Komori ,  Toshihiro Yamamoto ,  Megumi Matsumoto

IPC分类号： H01L51/54

CPC分类号： C07D487/14 ,  C07D519/00 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1011 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/1059 ,  H01L51/0072 ,  H01L51/0085 ,  H01L51/5012 ,  H05B33/10

摘要： Disclosed is an organic electroluminescent device (organic EL device) that is improved in luminous efficiency, sufficiently secures driving stability, and has a simple configuration. This organic EL device has a light-emitting layer between an anode and a cathode piled one upon another on a substrate and the said light-emitting layer contains a fused polycyclic compound in which seven or more rings are fused together as a host material. The aforementioned fused polycyclic compound has a structure formed by fusing two or more indole rings to a carbazole ring. A specific example thereof is the compound represented by the following formula.

摘要翻译： 公开了一种提高发光效率的有机电致发光器件（有机EL器件），足够确保驱动稳定性，并且具有简单的结构。 该有机EL元件具有在基板上彼此堆叠的阳极和阴极之间的发光层，并且所述发光层含有其中7个以上的环作为主体材料熔合在一起的稠合多环化合物。 上述稠合多环化合物具有通过将两个或更多个吲哚环与咔唑环熔融而形成的结构。 其具体实例是由下式表示的化合物。

公开(公告)号：US09156843B2

公开(公告)日：2015-10-13

申请号：US13577238

申请日：2011-01-27

申请人： Takahiro Kai ,  Masaki Komori ,  Toshihiro Yamamoto ,  Megumi Matsumoto

发明人： Takahiro Kai ,  Masaki Komori ,  Toshihiro Yamamoto ,  Megumi Matsumoto

IPC分类号： H01L51/54 ,  C09K11/06 ,  C07D487/04 ,  H01L51/00 ,  H05B33/14 ,  C07D487/14 ,  C07D471/14 ,  C07D519/00 ,  H01L51/50

CPC分类号： C07D487/04 ,  C07D471/14 ,  C07D487/14 ,  C07D519/00 ,  C09K11/06 ,  C09K2211/1044 ,  H01L51/0067 ,  H01L51/0072 ,  H01L51/0074 ,  H01L51/0085 ,  H01L51/5012 ,  H01L51/5016 ,  H01L51/5048 ,  H01L51/5096 ,  H05B33/14

摘要： Disclosed is an organic electroluminescent device (organic EL device) that is improved in luminous efficiency, sufficiently secures driving stability, and has a simple configuration. This organic EL device is constituted of an anode, organic layers comprising a phosphorescent light-emitting layer, and a cathode piled one upon another on a substrate and at least one organic layer selected from a light-emitting layer, an electron-transporting layer, and a hole-blocking layer contains an indolocarbazole compound represented by general formula (1). In the case where the indolocarbazole compound is incorporated in the light-emitting layer containing a phosphorescent dopant and a host material, it is incorporated as the host material. Some of such indolocarbazole compounds are represented by the following formula (2): wherein each of A1 and A2 is an aromatic hydrocarbon group; each of B1 and B2 is an aromatic heterocyclic group; each of R1 to R3 is a hydrogen atom, an alkyl group, a cycloalkyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group; m is an integer of 1 to 3; and n is an integer of 0 to 3.

摘要翻译： 公开了一种提高发光效率的有机电致发光器件（有机EL器件），足够确保驱动稳定性，并且具有简单的结构。 该有机EL器件由阳极，包含磷光发光层的有机层和在基板上彼此堆叠的阴极和至少一个选自发光层，电子传输层， 空穴阻挡层含有通式（1）表示的吲哚并咔唑化合物。 在含有磷光掺杂剂和主体材料的发光层中并入吲哚咔唑化合物的情况下，作为主体材料。 一些这样的吲哚咔唑化合物由下式（2）表示：其中A1和A2各自为芳族烃基; B1和B2各自为芳族杂环基; R 1〜R 3各自为氢原子，烷基，环烷基，芳香族烃基或芳香族杂环基; m为1〜3的整数。 n为0〜3的整数。

公开(公告)号：US09133205B2

公开(公告)日：2015-09-15

申请号：US13578207

申请日：2011-02-07

申请人： Takahiro Kai ,  Masaki Komori ,  Toshihiro Yamamoto ,  Megumi Matsumoto

发明人： Takahiro Kai ,  Masaki Komori ,  Toshihiro Yamamoto ,  Megumi Matsumoto

IPC分类号： H01L51/54 ,  C09K11/06 ,  C07D487/14 ,  C07D519/00 ,  H01L51/00 ,  H05B33/10 ,  H01L51/50

CPC分类号： C07D487/14 ,  C07D519/00 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1011 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/1059 ,  H01L51/0072 ,  H01L51/0085 ,  H01L51/5012 ,  H05B33/10

摘要： Disclosed is an organic electroluminescent device (organic EL device) that is improved in luminous efficiency, sufficiently secures driving stability, and has a simple configuration. This organic EL device has a light-emitting layer between an anode and a cathode piled one upon another on a substrate and the said light-emitting layer contains a fused polycyclic compound in which seven or more rings are fused together as a host material. The aforementioned fused polycyclic compound has a structure formed by fusing two or more indole rings to a carbazole ring. A specific example thereof is the compound represented by the following formula.

摘要翻译： 公开了一种提高发光效率的有机电致发光器件（有机EL器件），足够确保驱动稳定性，并且具有简单的结构。 该有机EL元件具有在基板上彼此堆叠的阳极和阴极之间的发光层，并且所述发光层含有其中7个以上的环作为主体材料熔合在一起的稠合多环化合物。 上述稠合多环化合物具有通过将两个或更多个吲哚环与咔唑环熔融而形成的结构。 其具体实例是由下式表示的化合物。

公开(公告)号：US20130207097A1

公开(公告)日：2013-08-15

申请号：US13881715

申请日：2011-11-21

申请人： Takahiro Kai ,  Masaki Komori ,  Toshihiro Yamamoto ,  Tohru Asari ,  Takaya Ishiyama ,  Megumi Matsumoto

发明人： Takahiro Kai ,  Masaki Komori ,  Toshihiro Yamamoto ,  Tohru Asari ,  Takaya Ishiyama ,  Megumi Matsumoto

IPC分类号： H01L51/00

CPC分类号： H01L51/0072 ,  C07D487/04 ,  C07D487/22 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1022 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/1059 ,  C09K2211/1092 ,  H01L51/0067 ,  H01L51/0085 ,  H01L51/5016 ,  H01L51/5056 ,  H01L51/5072 ,  H01L51/5096 ,  H05B33/14

摘要： Provided is an organic electroluminescent device (EL device) that uses an indolocarbazole compound. The organic EL device includes an anode, a plurality of organic layers including a phosphorescent light-emitting layer, and a cathode laminated on a substrate, in which at least one organic layer selected from the phosphorescent light-emitting layer, a hole-transporting layer, an electron-transporting layer, and a hole-blocking layer contains an indolocarbazole compound represented by the general formula (1). In the general formula (1), a ring I and a ring II represent rings represented by the formula (1a) and the formula (1b), respectively, each of which are fused to an adjacent ring. X's each represent nitrogen or C—Y and at least one of X's represents nitrogen. Y's each represent hydrogen, an alkyl group, a cycloalkyl group, or an aromatic group. A represents an alkyl group, a cycloalkyl group, or an aromatic group. At least one of Y and A represents an alkyl group or a cycloalkyl group. R's each represent hydrogen, an alkyl group, a cycloalkyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group.

摘要翻译： 提供了使用吲哚并咔唑化合物的有机电致发光器件（EL器件）。 有机EL器件包括阳极，包括磷光发光层的多个有机层和层叠在基板上的阴极，其中至少一个选自磷光发光层的有机层，空穴传输层 ，电子传输层和空穴阻挡层含有由通式（1）表示的吲哚咔唑化合物。 在通式（1）中，环I和环II分别表示与式（1a）和式（1b）表示的环，它们各自与相邻的环稠合。 X各自表示氮或C-Y，X中的至少一个表示氮。 Y各自表示氢，烷基，环烷基或芳基。 A表示烷基，环烷基或芳基。 Y和A中至少一个表示烷基或环烷基。 R 3各自表示氢，烷基，环烷基，芳香族烃基或芳香族杂环基。