公开(公告)号：US09978962B2

公开(公告)日：2018-05-22

申请号：US14725332

申请日：2015-05-29

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Tomoka Hara ,  Satoshi Seo ,  Toshiki Sasaki ,  Kunihiko Suzuki

IPC: H01L51/00 ,  C07F15/00 ,  C09K11/06 ,  H05B33/14 ,  H01L51/50

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1044 ,  C09K2211/185 ,  H01L51/5016 ,  H05B33/14

Abstract: To provide a long-lifetime organometallic iridium complex exhibiting yellow light emission with high emission efficiency as a novel substance. The organometallic iridium complex includes a ligand in which an unsubstituted phenyl group is bonded to each of the 2-position and the 5-position of pyrimidine. The organometallic iridium complex has a structure represented by General Formula (G1).

公开(公告)号：US20180102488A1

公开(公告)日：2018-04-12

申请号：US15836079

申请日：2017-12-08

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Tomoya Yamaguchi ,  Hiromi Seo ,  Satoshi Seo ,  Kunihiko Suzuki ,  Miki Kanamoto

IPC: H01L51/00 ,  C09K11/02 ,  C09K11/06 ,  H05B33/10 ,  C07F15/00 ,  H01L51/50

Abstract: As a novel substance having a novel skeleton, an organometallic complex with high emission efficiency which achieves improved color purity by a reduction of half width of an emission spectrum is provided. One embodiment of the present invention is an organometallic complex in which a β-diketone and a six-membered heteroaromatic ring including two or more nitrogen atoms inclusive of a nitrogen atom that is a coordinating atom are ligands. In General Formula (G1), X represents a substituted or unsubstituted six-membered heteroaromatic ring including two or more nitrogen atoms inclusive of a nitrogen atom that is a coordinating atom. Further, R1 to R4 each represent a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

公开(公告)号：US09793498B2

公开(公告)日：2017-10-17

申请号：US15184197

申请日：2016-06-16

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Masakazu Egawa ,  Satoshi Seo

IPC: H01L51/54 ,  C09K11/06 ,  H01L51/00 ,  C07F15/00 ,  H01L51/50 ,  H01L27/32 ,  H01L51/52

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C07F15/0046 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1022 ,  C09K2211/1048 ,  C09K2211/1059 ,  C09K2211/185 ,  H01L27/3211 ,  H01L27/3244 ,  H01L51/008 ,  H01L51/0087 ,  H01L51/009 ,  H01L51/5016 ,  H01L51/5056 ,  H01L51/5203

Abstract: It is an object of the present invention to provide an organometallic complex that can emit phosphorescence. In the following general formula (G1), X represents —O— or —N(R10)—. R1 to R9 each represent any of hydrogen, an alkyl group or a cycloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkoxycarbonyl group having 1 to 6 carbon atoms, an acyl group having 1 to 6 carbon atoms, an acyloxy group having 1 to 6 carbon atoms, a halogen group, a haloalkyl group, and an aryl group having 6 to 12 carbon atoms. In addition, R10 represents any of an alkyl group or a cycloalkyl group having 1 to 6 carbon atoms, an acyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 carbon atoms, and a heteroaryl group having 4 to 10 carbon atoms. Moreover, M represents an element belonging to Group 9 or 10.

公开(公告)号：US09634279B2

公开(公告)日：2017-04-25

申请号：US14924054

申请日：2015-10-27

Applicant: Semiconductor Energy Laboratory Co., Ltd.

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

IPC: H01L51/50 ,  C09K11/06 ,  C07D409/10 ,  H01L51/00 ,  H05B33/14

CPC classification number: H01L51/5028 ,  C07D409/10 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1011 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/1088 ,  C09K2211/1092 ,  C09K2211/185 ,  H01L51/0056 ,  H01L51/0058 ,  H01L51/0059 ,  H01L51/006 ,  H01L51/0061 ,  H01L51/0072 ,  H01L51/0074 ,  H01L51/0085 ,  H01L51/5016 ,  H05B33/14

Abstract: A light-emitting element having high external quantum efficiency is provided. A light-emitting element having low drive voltage is provided. Provided is a light-emitting element which includes a light-emitting layer containing a phosphorescent compound, a first organic compound, and a second organic compound between a pair of electrodes. A combination of the first organic compound and the second organic compound forms an exciplex (excited complex). An emission spectrum of the exciplex overlaps with an absorption band located on the longest wavelength side of an absorption spectrum of the phosphorescent compound. A peak wavelength of the emission spectrum of the exciplex is longer than or equal to a peak wavelength of the absorption band located on the longest wavelength side of the absorption spectrum of the phosphorescent compound.

公开(公告)号：US09406895B2

公开(公告)日：2016-08-02

申请号：US14688429

申请日：2015-04-16

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Satoko Shitagaki ,  Satoshi Seo

IPC: H01L51/00 ,  C07F15/00 ,  C09K11/06 ,  H05B33/14 ,  H01L51/50 ,  H01L51/52

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/185 ,  H01L51/5016 ,  H01L51/504 ,  H01L51/5056 ,  H01L51/5072 ,  H01L51/5088 ,  H01L51/5092 ,  H01L51/5206 ,  H01L51/5221 ,  H01L51/5278 ,  H01L51/56 ,  H01L2251/301 ,  H01L2251/306 ,  H05B33/14

Abstract: To provide a novel organometallic complex, and light emitting elements, light emitting devices, and electronic devices which include the organometallic complex. In addition, to provide a composition in which the organometallic complex is dissolved and to provide a method for manufacturing light emitting elements using the composition. An organometallic complex has high solubility in a solvent. In the organometallic complex, the ligand including a pyrazine skeleton is bound to an atom belonging to Group 9 (Co, Rh, or Ir) or an atom belonging to Group 10 (Ni, Pd, or Pt). In addition, the light emission efficiency is high. Therefore, the organometallic complex is preferably used for manufacturing a light emitting element.

公开(公告)号：US09312498B2

公开(公告)日：2016-04-12

申请号：US14483743

申请日：2014-09-11

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Hiroki Suzuki ,  Hiromi Seo ,  Tatsuyoshi Takahashi ,  Satoshi Seo

IPC: H01L51/00 ,  H01L51/50

CPC classification number: H01L51/0072 ,  H01L51/0074 ,  H01L51/5016

Abstract: A novel organic compound is provided. In addition, a novel organic compound with high heat resistance is provided. In the organic compound, a dibenzoquinoxaline skeleton and a 4,4-bidibenzofuran skeleton or a 4,4′-bidibezothiophene skeleton are connected to each other through an arylene group.

Abstract translation: 提供了一种新颖的有机化合物。 另外，提供了具有高耐热性的新型有机化合物。 在有机化合物中，二苯并喹喔啉骨架和4,4'-二苯并呋喃骨架或4,4'-二溴噻吩骨架通过亚芳基彼此连接。

公开(公告)号：US09269920B2

公开(公告)日：2016-02-23

申请号：US14504826

申请日：2014-10-02

Applicant: Semiconductor Energy Laboratory Co., Ltd.

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

IPC: H01L29/08 ,  H01L21/00 ,  H01L51/50 ,  H01L27/32 ,  H01L51/00

CPC classification number: H01L51/504 ,  H01L27/3209 ,  H01L51/0059 ,  H01L51/0061 ,  H01L51/0071 ,  H01L51/0072 ,  H01L51/0074 ,  H01L51/0085 ,  H01L51/5016 ,  H01L51/5056 ,  H01L51/5072 ,  H01L2251/5346 ,  H01L2251/5376 ,  H01L2251/5384

Abstract: A light-emitting element having extremely high efficiency of approximately 25% is provided. The light-emitting element includes a light-emitting layer which contains a phosphorescent guest, an n-type host, and a p-type host, where the light-emitting layer is interposed between an n-type layer including the n-type host and a p-type layer including the p-type host, and where the n-type host and the p-type host are able to form an exciplex in the light-emitting layer. The light-emitting element exhibits an extremely high emission efficiency (power efficiency of 74.3 lm/W, external quantum efficiency of 24.5%, energy efficiency of 19.3%) at a low driving voltage (2.6 V) at which luminance of 1200 cd/m2 is attainable.

Abstract translation: 提供了具有极高效率约25％的发光元件。 发光元件包括含有磷光客体，n型主体和p型主体的发光层，其中发光层插入在包括n型主体的n型层之间 以及包含p型主体的p型层，其中n型主体和p型主体能够在发光层中形成激光复合物。 在1200cd / m2的亮度的低驱动电压（2.6V）下，发光元件显示出极高的发光效率（74.3lm / W的功率效率，24.5％的外部量子效率，能量效率为19.3％） 是可以实现的

公开(公告)号：US09219236B2

公开(公告)日：2015-12-22

申请号：US14062102

申请日：2013-10-24

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Satoshi Seo ,  Satoko Shitagaki ,  Hiroko Abe

IPC: H01L51/54 ,  H01L51/00 ,  C07F15/00 ,  C09K11/06 ,  H05B33/14 ,  H01L51/50

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C09K11/06 ,  C09K2211/1044 ,  C09K2211/185 ,  H01L51/5016 ,  H05B33/14

Abstract: An organometallic complex according to the present invention comprises a structure represented by the following general formula (1). In the formula, R1 to R5 are any one selected from the group consisting of hydrogen, a halogen element, an acyl group, an alkyl group, an alkoxy group, an aryl group, a cyano group, and a heterocyclic group, Ar is an aryl group having an electron-withdrawing group or a heterocyclic group having electron-drawing group, and M is an element of Group 9 or an element of Group 10.

Abstract translation: 根据本发明的有机金属络合物包含由以下通式（1）表示的结构。 在该式中，R 1至R 5为选自氢，卤素元素，酰基，烷基，烷氧基，芳基，氰基和杂环基中的任何一个，Ar为 具有吸电子基团的芳基或具有电子吸引基团的杂环基，M是第9族元素或第10族元素。

公开(公告)号：US09196844B2

公开(公告)日：2015-11-24

申请号：US13905829

申请日：2013-05-30

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Tomoya Yamaguchi ,  Yasushi Kitano ,  Hiromi Seo ,  Satoshi Seo

IPC: C07D241/42 ,  C07D409/10 ,  H01L51/54 ,  H01L51/00 ,  H01L51/50 ,  H01L51/52 ,  H01L27/32

CPC classification number: H01L51/0071 ,  C07D241/42 ,  C07D409/10 ,  H01L27/3206 ,  H01L51/0072 ,  H01L51/0074 ,  H01L51/0085 ,  H01L51/5016 ,  H01L51/5028 ,  H01L51/5265 ,  H01L51/5278 ,  H01L2251/308

Abstract: A novel method includes a synthetic pathway in which α-diketone and a 1-(haloaryl)ethane-1,2-diamine derivative are cyclized to each other to form a 2-(haloaryl)pyrazine derivative. Further, a 2-arylpyrazine derivative having an aryl group or a heteroaryl group as a substituent is synthesized by coupling the 2-(haloaryl)pyrazine derivative obtained by the above synthetic pathway and an arylboronic acid or a heteroarylboronic acid. The 2-arylpyrazine derivative obtained by the novel method is useful for a light-emitting element, a light-emitting device, an electronic device, or a lighting device with high emission efficiency.

Abstract translation: 一种新的方法包括其中α-二酮和1-（卤代芳基）乙烷-1,2-二胺衍生物彼此环化以形成2-（卤代芳基）吡嗪衍生物的合成途径。 此外，通过将通过上述合成路径获得的2-（卤代芳基）吡嗪衍生物与芳基硼酸或杂芳基硼酸偶联，合成具有芳基或杂芳基作为取代基的2-芳基吡嗪衍生物。 通过该方法获得的2-芳基吡嗪衍生物可用于发光元件，发光器件，电子器件或发光效率高的照明器件。

公开(公告)号：US09159934B2

公开(公告)日：2015-10-13

申请号：US13905720

申请日：2013-05-30

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Yasushi Kitano ,  Takao Hamada ,  Satoshi Seo ,  Hiroki Suzuki ,  Tomohiro Kubota

IPC: H01L21/00 ,  H01L51/00

CPC classification number: H01L51/0072 ,  H01L51/006 ,  H01L51/0074 ,  H01L51/0085 ,  H01L2251/308

Abstract: A novel organic material with fewer impurities, a light-emitting element including the organic material, and a light-emitting device, an electronic appliance, and a lighting device each of which includes the light-emitting element are provided. The organic material is obtained by coupling an aryl halide and an aryl boronic acid or an aryl boronic acid ester. The aryl boronic acid or the aryl boronic acid ester includes at least one of a first impurity in which a boryl group of the aryl boronic acid or the aryl boronic acid ester is substituted by hydrogen and a second impurity in which a molecular mass of 16 or 17 is added to the molecular mass of the first impurity. The concentration of an impurity other than the first impurity and the second impurity is 1% or lower.

Abstract translation: 提供了具有较少杂质的新型有机材料，包括有机材料的发光元件，以及包括发光元件的发光装置，电子设备和照明装置。 有机材料通过偶合芳基卤和芳基硼酸或芳基硼酸酯而获得。 芳基硼酸或芳基硼酸酯包括其中芳基硼酸或芳基硼酸酯的硼基被氢取代的第一杂质和第二杂质中的至少一种，其中分子量为16或 17添加到第一杂质的分子量。 除了第一杂质和第二杂质以外的杂质的浓度为1％以下。