公开(公告)号：US09412953B2

公开(公告)日：2016-08-09

申请号：US13958072

申请日：2013-08-02

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Miyako Morikubo ,  Naoaki Hashimoto ,  Hiromi Seo ,  Satoshi Seo ,  Miki Kanamoto ,  Tomoka Nakagawa

IPC: H01L51/50 ,  H01L51/00

CPC classification number: H01L51/0067 ,  C07D409/10 ,  C09K11/025 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1044 ,  C09K2211/185 ,  H01L51/0052 ,  H01L51/0058 ,  H01L51/0059 ,  H01L51/006 ,  H01L51/0061 ,  H01L51/0072 ,  H01L51/0074 ,  H01L51/0085 ,  H01L51/5004 ,  H01L51/5016 ,  H01L51/5024 ,  H01L51/5072

Abstract: A light-emitting element with high heat resistance and high emission efficiency is provided. A novel heterocyclic compound that can be used in such a light-emitting element is provided. One embodiment of the present invention is a light-emitting element which includes, between a pair of electrodes, a layer containing a first organic compound, a second organic compound, and a light-emitting substance; the first organic compound includes one pyrimidine ring and one ring with a hole-transport skeleton; the second organic compound is an aromatic amine; and the light-emitting substance converts triplet excitation energy into light. A combination of the first organic compound, which includes the one pyrimidine ring and the one ring with the hole-transport skeleton, and the second organic compound, which is the aromatic amine, forms an exciplex.

Abstract translation: 提供具有高耐热性和高发光效率的发光元件。 可以提供可用于这种发光元件的新型杂环化合物。 本发明的一个实施方案是一种发光元件，其在一对电极之间包括含有第一有机化合物，第二有机化合物和发光物质的层; 第一有机化合物包括一个嘧啶环和一个具有空穴传输骨架的环; 第二有机化合物是芳族胺; 并且发光物质将三重态激发能量转换成光。 第一有机化合物（其包括一个嘧啶环和具有空穴传输骨架的一个环）和作为芳族胺的第二有机化合物的组合形成激元复合体。

公开(公告)号：US20160155960A1

公开(公告)日：2016-06-02

申请号：US15014509

申请日：2016-02-03

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Nobuharu Ohsawa ,  Hideko Inoue ,  Satoshi Seo ,  Satoko Shitagaki

IPC: H01L51/00 ,  C09K11/02 ,  C09K11/06

CPC classification number: H01L51/0085 ,  C09K11/025 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1022 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/185 ,  H01L51/0072 ,  H01L51/009 ,  H01L51/5016 ,  H01L51/5052 ,  H05B33/14 ,  Y10S428/917

Abstract: The light emitting element includes a first electrode and a second electrode, between which a light emitting layer, a hole transporting layer provide in contact with the light emitting layer, an electron transporting layer provided in contact with the light emitting layer, and a mixed layer provided between the electron transporting layer and the second electrode. The mixed layer includes an electron transporting substance and a substance showing an electron donating property with respect to the electron transporting substance. The light emitting layer includes an organometallic complex represented in General Formula (1) and a host. R1 and R2 each represent an electron-withdrawing substituent group. R3 and R4 each represent any of hydrogen or an alkyl group having 1 to 4 carbon atoms. L represents any of a monoanionic ligand having a beta-diketone structure, a monoanionic bidentate chelating ligand having a carboxyl group, or a monoanionic bidentate chelating ligand having a phenolic hydroxyl group.

Abstract translation: 发光元件包括第一电极和第二电极，在该第一电极和第二电极之间，发光层，与发光层接触的空穴传输层，与发光层接触设置的电子传输层，以及混合层 设置在电子传输层和第二电极之间。 该混合层包括电子传输物质和相对于电子传输物质显示给电子性的物质。 发光层包括通式（1）表示的有机金属络合物和主体。 R1和R2各自表示吸电子取代基。 R 3和R 4各自表示氢或碳原子数为1〜4的烷基中的任一个。 L表示具有β-二酮结构的单阴离子配体，具有羧基的单阴离子二齿螯合配体或具有酚羟基的单阴离子二齿螯合配体中的任一种。

公开(公告)号：US09276222B2

公开(公告)日：2016-03-01

申请号：US14313294

申请日：2014-06-24

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Miki Kanamoto ,  Hiromi Seo ,  Tatsuyoshi Takahashi ,  Satoshi Seo

IPC: H01L51/00 ,  C07F15/00 ,  C09K11/06 ,  H01L51/50

CPC classification number: H01L51/0085 ,  C07F15/00 ,  C07F15/0033 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/1059 ,  C09K2211/185 ,  H01L51/5016

Abstract: Provided as a novel substance is a long-lifetime organometallic iridium complex emitting yellow light with high emission efficiency. The organometallic iridium complex is represented by General Formula (G1) and has a structure in which a phenyl group whose 2-position and 6-position are each substituted by an alkyl group is bonded to the 4-position of pyrimidine. In General Formula (G1), R1 and R2 each independently represent a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

Abstract translation: 作为一种新型物质提供长寿命有机金属铱络合物，发射具有高发射效率的黄光。 有机金属铱络合物由通式（G1）表示，其中2位和6位的苯基均被烷基取代的结构键合到嘧啶的4-位上。 在通式（G1）中，R 1和R 2各自独立地表示取代或未取代的碳原子数1〜6的烷基。

公开(公告)号：US09184398B2

公开(公告)日：2015-11-10

申请号：US14584362

申请日：2014-12-29

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Tomoya Yamaguchi ,  Satoko Shitagaki ,  Takahiro Ushikubo ,  Satoshi Seo ,  Yui Yamada ,  Hiromi Nowatari

IPC: C07D239/24 ,  C01G55/00 ,  H01L51/00 ,  C07F15/00 ,  C09K11/06 ,  H05B33/14 ,  H01L27/32 ,  H01L51/50 ,  H01L51/52 ,  H01L27/18

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1011 ,  C09K2211/1044 ,  C09K2211/185 ,  H01L27/18 ,  H01L27/3244 ,  H01L27/3283 ,  H01L51/009 ,  H01L51/5012 ,  H01L51/5016 ,  H01L51/5044 ,  H01L51/5278 ,  H01L2251/5361 ,  H05B33/14

Abstract: Provided is a novel substance that can emit phosphorescence. Alternatively, provided is a novel substance with high emission efficiency. An organometallic complex in which a 4-arylpyrimidine derivative is a ligand and iridium is a central metal is provided. Specifically, an organometallic complex having a structure represented by a general formula (G1) is provided. In the general formula (G1), R1 represents a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, R2 represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and a substituted or unsubstituted phenyl group, R3 represents hydrogen or a substituted or unsubstituted alkyl group having 1 to 4 carbon atoms, and Ar1 represents a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.

Abstract translation: 提供可以发射磷光的新物质。 或者，提供了具有高排放效率的新型物质。 提供其中4-芳基嘧啶衍生物为配体和铱为中心金属的有机金属配合物。 具体地说，提供具有由通式（G1）表示的结构的有机金属络合物。 在通式（G1）中，R 1表示取代或未取代的碳原子数1〜4的烷基或取代或未取代的碳数为6〜10的芳基，R 2表示氢，取代或未取代的烷基， 至4个碳原子，以及取代或未取代的苯基，R 3表示氢或取代或未取代的碳原子数1〜4的烷基，Ar 1表示取代或未取代的碳数为6〜10的亚芳基。

公开(公告)号：US20150287936A1

公开(公告)日：2015-10-08

申请号：US14745015

申请日：2015-06-19

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Tomoka Nakagawa ,  Nobuharu Ohsawa ,  Satoshi Seo ,  Yui Yamada

IPC: H01L51/00 ,  C07F15/00 ,  C09K11/06

Abstract: Provided are organometallic complexes that can exhibit phosphorescence. One of the novel organometallic complexes is represented by General Formula (G1). In General Formula (G1), R1 represents any of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms which may have a substituent, and an aralkyl group having 7 to 10 carbon atoms which may have a substituent. In addition, R2 represents any of an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms which may have a substituent, and an aryl group having 6 to 12 carbon atoms which may have a substituent. Further, Ar represents an arylene group having 6 to 13 carbon atoms which may have a substituent. Further, M represents a Group 9 element or a Group 10 element.

Abstract translation: 提供可以显示磷光的有机金属络合物。 新型有机金属配合物之一由通式（G1）表示。 在通式（G1）中，R 1表示碳原子数1〜6的烷基，可以具有取代基的碳原子数5〜8的环烷基，碳原子数7〜10的芳烷基，可以具有 取代基。 此外，R 2表示可以具有取代基的碳原子数1〜6的烷基，碳原子数5〜8的环烷基，碳原子数6〜12的可具有取代基的芳基。 此外，Ar表示可以具有取代基的碳原子数6〜13的亚芳基。 此外，M表示第9族元素或第10族元素。

公开(公告)号：US20150073142A1

公开(公告)日：2015-03-12

申请号：US14482536

申请日：2014-09-10

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Nobuharu Ohsawa ,  Hideko Inoue ,  Satoshi Seo ,  Miki Kanamoto

IPC: H01L51/00

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/185 ,  H01L51/0059 ,  H01L51/0072 ,  H01L51/0074 ,  H01L51/5016 ,  H01L51/5056 ,  H01L51/5072 ,  H01L51/5088 ,  H01L51/5092 ,  H01L51/5234 ,  H01L51/56 ,  H01L2251/5384 ,  H05B33/14

Abstract: An organometallic iridium complex has high emission efficiency and a long lifetime. The iridium complex includes the structure represented by Formula (G1). In the formula, Ar represents a substituted or unsubstituted arylene group having 6 to 13 carbon atoms. R1 to R6 independently represent any one of hydrogen and a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, and one of R2 and R6 represents the alkyl group. X represents a carbon atom or a nitrogen atom, and when X represents a carbon atom, hydrogen or an alkyl group having 1 to 6 carbon atoms is bonded to the carbon atom. A dihedral angle between a ring bonded to R1 and a phenyl group bonded to R2 to R6 is 30° or more and 90° or less. An interior angle of the pyridine/pyrimidine ring facing R1 is within a range of 118° to 122°.

Abstract translation: 有机金属铱络合物的发光效率高，使用寿命长。 铱络合物包括由式（G1）表示的结构。 在该式中，Ar表示取代或未取代的碳原子数6〜13的亚芳基。 R 1〜R 6独立地表示氢和取代或未取代的碳原子数1〜6的烷基中的任一个，R 2和R 6中的一个表示烷基。 X表示碳原子或氮原子，当X表示碳原子时，碳原子上含有碳原子数1〜6的烷基或碳原子数1〜6的烷基。 结合到R 1的环与与R 2至R 6结合的苯基之间的二面角为30°以上且90°以下。 面向R1的吡啶/嘧啶环的内角在118°至122°的范围内。

公开(公告)号：US20140371448A1

公开(公告)日：2014-12-18

申请号：US14473000

申请日：2014-08-29

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Satoshi Seo

IPC: H01L51/00

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C07F15/0086 ,  H01L51/5012

Abstract: An object is to provide a novel organometallic complex capable of emitting phosphorescence, an organometallic complex which exhibits deep red emission, and a light-emitting element which provides deep red emission. Provided is an organometallic complex having a structure represented by the following General Formula (G1). In the formula, R1, R2, R3, R4, R5, R6, R7, R8, and R9 represent substituents, and M is a central metal and represents either a Group 9 element or a Group 10 element.

Abstract translation: 目的是提供一种能够发射磷光的新型有机金属配合物，呈现深红色发射的有机金属络合物，以及提供深红色发射的发光元件。 提供具有由以下通式（G1）表示的结构的有机金属络合物。 在该式中，R 1，R 2，R 3，R 4，R 5，R 6，R 7，R 8和R 9表示取代基，M是中心金属，表示第9族元素或第10族元素。

公开(公告)号：US20140367662A1

公开(公告)日：2014-12-18

申请号：US14300695

申请日：2014-06-10

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Tomoya Yamaguchi ,  Hiromi Seo ,  Tatsuyoshi Takahashi ,  Satoshi Seo

IPC: H01L51/00 ,  H01L51/50

CPC classification number: H01L51/0085 ,  C07F15/0033

Abstract: An organometallic iridium complex that has high emission efficiency and a long lifetime and emits deep red light (emission wavelength: around 700 nm) is provided. The organometallic iridium complex has a ligand that is represented by General Formula (G0) and has at least a dimethyl phenyl group and a quinoxaline skeleton. In the formula, R1 to R3 separately represent an alkyl group having 1 to 6 carbon atoms, a phenyl group, or a phenyl group having an alkyl group having 1 to 6 carbon atoms as a substituent.

Abstract translation: 提供了具有高发光效率和长寿命且发出深红光（发射波长：约700nm）的有机金属铱络合物。 有机金属铱络合物具有由通式（G0）表示的配体，并且具有至少二甲基苯基和喹喔啉骨架。 式中，R 1〜R 3分别表示碳原子数1〜6的烷基，苯基或具有碳原子数1〜6的烷基的苯基作为取代基。

公开(公告)号：US20140179920A1

公开(公告)日：2014-06-26

申请号：US14195108

申请日：2014-03-03

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Nobuharu OHSAWA ,  Satoko SHITAGAKI ,  Satoshi SEO

IPC: H01L51/00

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C07F15/0086 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1014 ,  C09K2211/1044 ,  C09K2211/185 ,  H01L51/5012

Abstract: An object is to provide an organometallic complex whose phosphorescence characteristics can be adjusted by varying the structure of a ligand. Alternatively, an object is to provide an organometallic complex capable of emitting yellow phosphorescence with high luminance. Alternatively, an object is to provide a light-emitting device with high added value. An organometallic complex which has a structure represented by a general formula (G1) below and at least one substituent group represented by a general formula (G2) below as a phenyl group and is formed in such a way that a phenylpyrazine derivative represented by a general formula (G0) below is ortho-metalated by an ion of a Group 9 metal or of a Group 10 metal is provided. Alternatively, a light-emitting element and a light-emitting device formed including the organometallic complex are provided.

Abstract translation: 目的是提供一种有机金属配合物，其磷光特性可以通过改变配体的结构来调节。 或者，目的是提供能够以高亮度发射黄色磷光的有机金属络合物。 或者，目的在于提供具有高附加值的发光装置。 一种有机金属络合物，其具有下述通式（G1）表示的结构和至少一个由以下通式（G2）表示的取代基作为苯基，并且以这样的方式形成，使得由通式 下面的式（G0）由9族金属的离子或10族金属进行邻金属化。 或者，提供了包括有机金属络合物的发光元件和形成的发光器件。

公开(公告)号：US20140084274A1

公开(公告)日：2014-03-27

申请号：US14030554

申请日：2013-09-18

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Shunpei Yamazaki ,  Satoshi Seo ,  Satoko Shitagaki ,  Nobuharu Ohsawa ,  Hideko Inoue ,  Hiroshi Kadoma ,  Harue Osaka

IPC: H01L51/50

CPC classification number: H01L51/5004 ,  H01L51/5008 ,  H01L51/5016 ,  H01L2251/5384

Abstract: A light-emitting element with high emission efficiency is provided. The light-emitting element includes, between a pair of electrodes, a layer containing a p-type host, a light-emitting layer containing a guest, the p-type host, and an n-type host, and a layer containing the n-type host. A combination of the p-type host and the n-type host forms an exciplex. Among the layer containing the p-type host, the light-emitting layer, and the layer containing the n-type host, the light-emitting layer has the highest secondary ion intensity of the n-type host, the layer containing the n-type host has the second-highest secondary ion intensity of the n-type host, and the layer containing the p-type host has the lowest secondary ion intensity of the n-type host in analysis by a time-of-flight secondary ion mass spectrometer.

Abstract translation: 提供发光效率高的发光元件。 发光元件在一对电极之间包括含有p型主体的层，包含客体的发光层，p型主体和n型主体，以及含有n型主体的层 型主机。 p型宿主和n型宿主的组合形成一个激元复合体。 在含有p型主体，发光层和含有n型主体的层中，发光层具有最高的n型主体的二次离子强度， 类型的主体具有n型主体的次高次要离子强度，并且包含p型主体的层在分析中通过飞行时间次级离子质量具有最低的n型主体的二次离子强度 光谱仪