公开(公告)号：US20200295267A1

公开(公告)日：2020-09-17

申请号：US16809951

申请日：2020-03-05

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Miki KANAMOTO ,  Hideko INOUE ,  Tatsuyoshi TAKAHASHI ,  Hiromitsu KIDO ,  Satoshi SEO

IPC: H01L51/00 ,  C07D491/048 ,  C09K11/06

Abstract: A compound includes a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton, a first substituent, and a second substituent. Each of the first substituent and the second substituent includes a furan skeleton, a thiophene skeleton, or a pyrrole skeleton. The first substituent is bonded to a pyrimidine ring included in the benzofuropyrimidine skeleton or a pyrimidine ring included in the benzothienopyrimidine skeleton. The second substituent is bonded to a benzene ring included in the benzofuropyrimidine skeleton or a benzene ring included in the benzothienopyrimidine skeleton. The light-emitting element includes the compound.

公开(公告)号：US20200006673A1

公开(公告)日：2020-01-02

申请号：US16570062

申请日：2019-09-13

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Satoshi Seo ,  Takao HAMADA ,  Tatsuyoshi TAKAHASHI ,  Yasushi KITANO ,  Hiroki SUZUKI ,  Hideko INOUE

IPC: H01L51/00 ,  C07D403/14

Abstract: To provide a light-emitting element with an improved reliability, a light-emitting element with a high current efficiency (or a high quantum efficiency), and a novel dibenzo[f,h]quinoxaline derivative that is favorably used in a light-emitting element which is one embodiment of the present invention. A light-emitting element includes an EL layer between an anode and a cathode. The EL layer includes a light-emitting layer; the light-emitting layer contains a first organic compound having an electron-transport property and a hole-transport property, a second organic compound having a hole-transport property, and a light-emitting substance; the combination of the first organic compound and the second organic compound forms an exciplex; the HOMO level of the first organic compound is lower than the HOMO level of the second organic compound; and a difference between the HOMO level of the first organic compound and the HOMO level of the second organic compound is less than or equal to 0.4 eV.

公开(公告)号：US20170279063A1

公开(公告)日：2017-09-28

申请号：US15492439

申请日：2017-04-20

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Satoshi SEO ,  Satoko SHITAGAKI ,  Nobuharu OHSAWA ,  Hideko INOUE ,  Kunihiko SUZUKI

IPC: H01L51/50 ,  C07D409/10

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：US20170183368A1

公开(公告)日：2017-06-29

申请号：US15386432

申请日：2016-12-21

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Tomoka Hara ,  Miki KANAMOTO ,  Hideko INOUE ,  Satoshi SEO ,  Satomi MITSUMORI ,  Takeyoshi WATABE ,  Nobuharu OHSAWA

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

CPC classification number: C07F15/0086 ,  C07F15/0033 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1022 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/1059 ,  C09K2211/1074 ,  C09K2211/1096 ,  C09K2211/185 ,  H01L51/0085 ,  H01L51/0087 ,  H01L51/0094 ,  H01L51/5012 ,  H01L51/5016 ,  Y02P20/582

Abstract: A novel light-emitting material is provided. A novel orgnometallic complex is provided. An orgnometallic complex having a high carrier-transport property is provided. An orgnometallic complex having a deep HOMO level and/or a deep LUMO level is provided. An orgnometallic complex having a high charge-injection property is provided. Another object is to provide an organometallic complex that can exhibit yellow to blue phosphorescence. An organometallic complex that has a high carrier-transport property and exhibits green to blue phosphorescence is provided. An organometallic complex including a ligand having a structure of 5-(2-pyridinyl)-5H-benzimidazo[1,2-a]benzimidazole and a light-emitting material including the organometallic complex are provided.

公开(公告)号：US20170141330A1

公开(公告)日：2017-05-18

申请号：US15349608

申请日：2016-11-11

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Toshiaki Tsunoi ,  Hideko INOUE ,  Tomonori NAKAYAMA

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

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C09K11/06 ,  H01L51/5016 ,  Y02P20/582

Abstract: To provide a novel organometallic complex having high color purity. The organometallic complex is represented by General Formula (G1), and includes iridium and a ligand. The ligand includes a five-membered aromatic heterocycle including two or more nitrogen atoms and a plurality of aryl groups bonded to the five-membered aromatic heterocycle. At least one of the plurality of aryl groups includes a pentafluorosulfanyl group as a substituent. In General Formula (G1), one of P1 and P2 represents nitrogen and the other represents carbon, or both of P1 and P2 represent carbon; Q1 represents any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 5 to 8 carbon atoms, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms; Q2 represents any of hydrogen and a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; each of Ar1 and Ar2 independently represents a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; and any one of Q1, Ar1, and Ar2 includes a pentafluorosulfanyl group.

公开(公告)号：US20170062738A1

公开(公告)日：2017-03-02

申请号：US15248721

申请日：2016-08-26

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Tomoya YAMAGUCHI ,  Hideko INOUE ,  Tatsuyoshi TAKAHASHI

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

CPC classification number: H01L51/0087 ,  C07F15/0086 ,  C09K11/06 ,  C09K2211/185 ,  H01L51/5016

Abstract: A novel organometallic complex having high reliability is provided. The organometallic complex includes platinum and a ligand coordinated to the platinum. The ligand includes a plurality of pyridoindole skeletons. Each of the pyridoindole skeletons includes nitrogen bonded to the platinum. Each of the pyridoindole skeletons is bonded to an arylene group bonded to the platinum.

Abstract translation: 提供了具有高可靠性的新型有机金属络合物。 有机金属络合物包括铂和与铂配位的配体。 配体包括多个吡啶并吲哚骨架。 吡啶并吲哚骨架中的每一个都包括与铂结合的氮。 每个吡啶并吲哚骨架结合到与铂结合的亚芳基上。

公开(公告)号：US20160108006A1

公开(公告)日：2016-04-21

申请号：US14984262

申请日：2015-12-30

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko INOUE ,  Tomohiro KUBOTA ,  Miki KANAMOTO

IPC: C07D241/18

CPC classification number: C07D241/18 ,  C07D241/12 ,  C07F15/0033 ,  C09K11/06 ,  C09K2211/185 ,  H01L51/0085 ,  H01L51/5016 ,  H01L2251/308

Abstract: Provided is a 5,6-diaryl-2-pyrazyl triflate, its synthetic method, and a method for synthesizing an organometallic complex having a triarylpyrazine ligand from the 5,6-diaryl-2-pyrazyl triflate. The triflate is readily obtained from the corresponding 5,6-diarylpyrazin-2-ol, and the palladium-catalyzed coupling of the 5,6-diaryl-2-pyrazyl triflate with an arylboronic acid derivative leads to a high yield of a triarylpyrazine derivative having high purity. The use of the triarylpyrazine derivative in the reaction with a metal compound such as a metal chloride results in an ortho-metallated organometallic complex with high purity. The high purity of the organometallic complex contributes to the extremely high durability of a light-emitting element.

公开(公告)号：US20150340622A1

公开(公告)日：2015-11-26

申请号：US14717454

申请日：2015-05-20

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko INOUE ,  Tomoka HARA ,  Yasushi KITANO ,  Hiromi SEO ,  Tatsuyoshi TAKAHASHI ,  Satoshi SEO

IPC: H01L51/00 ,  C07D251/24 ,  C07D239/26 ,  H01L27/32 ,  C09K11/06

CPC classification number: H01L51/0067 ,  C07D239/26 ,  C07D251/24 ,  C09K11/06 ,  C09K2211/1011 ,  C09K2211/1044 ,  H01L27/3244 ,  H01L51/0058 ,  H01L51/0059 ,  H01L51/0072 ,  H01L51/0074 ,  H01L51/0085 ,  H01L51/5012

Abstract: Provided is a novel heterocyclic compound, a novel heterocyclic compound that can be used in a light-emitting element, or a highly reliable light-emitting device, electronic device, and lighting device in each of which the light-emitting element using the novel heterocyclic compound is used. One embodiment of the present invention is a heterocyclic compound represented by General Formula (G1). In General Formula (G1), each of A1 and A2 independently represents nitrogen or carbon bonded to hydrogen, and at least one of A1 and A2 represents nitrogen; Ar represents a substituted or unsubstituted arylene group having 6 to 18 carbon atoms; B represents a substituted or unsubstituted fluorenyl group; and R1 represents hydrogen, an alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 13 carbon atoms.

Abstract translation: 提供了可以用于发光元件的新型杂环化合物，新颖的杂环化合物或高度可靠的发光器件，电子器件和照明器件，其中使用新型杂环的发光元件 使用化合物。 本发明的一个实施方案是由通式（G1）表示的杂环化合物。 在通式（G1）中，A1和A2各自独立地表示与氢键合的氮或碳，A1和A2中的至少一个表示氮; Ar表示取代或未取代的碳原子数为6〜18的亚芳基。 B代表取代或未取代的芴基; 并且R 1表示氢，具有1至6个碳原子的烷基或具有6至13个碳原子的芳基。

公开(公告)号：US20140252338A1

公开(公告)日：2014-09-11

申请号：US14285754

申请日：2014-05-23

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Satoshi SEO ,  Satoko SHITAGAKI ,  Nobuharu OHSAWA ,  Hideko INOUE ,  Hiroshi KADOMA ,  Harue OSAKA ,  Shunpei YAMAZAKI

IPC: H01L51/50

CPC classification number: H01L51/5028 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1044 ,  C09K2211/185 ,  H01L51/0072 ,  H01L51/0074 ,  H01L51/0085 ,  H01L51/5016 ,  H01L51/5024 ,  H05B33/14

Abstract: To provide a light-emitting element with high emission efficiency or long lifetime, in which the use amount of a phosphorescent compound is small. To provide a light-emitting element including a light-emitting layer between a pair of electrodes, wherein the light-emitting layer includes a phosphorescent compound, a first organic compound, and a second organic compound, and the combination of the first organic compound and the second organic compound forms an exciplex. The light-emitting element transfers energy by utilizing the overlap between the emission spectrum of the exciplex and the absorption spectrum of the phosphorescent compound and thus has high energy transfer efficiency, even when the concentration of the phosphorescent compound is low.

Abstract translation: 为了提供磷光化合物的使用量小的发光效率高，寿命长的发光元件。 为了提供一种在一对电极之间包括发光层的发光元件，其中发光层包括磷光化合物，第一有机化合物和第二有机化合物，以及第一有机化合物和 第二有机化合物形成激元复合物。 发光元件利用激光复合物的发射光谱和磷光化合物的吸收光谱之间的重叠而传递能量，因此即使当磷光化合物的浓度低时，也具有高的能量转移效率。

公开(公告)号：US20140121372A1

公开(公告)日：2014-05-01

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: H01L51/00

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。