公开(公告)号：US20160293865A1

公开(公告)日：2016-10-06

申请号：US15092906

申请日：2016-04-07

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko INOUE ,  Takahiro ISHISONE ,  Nobuharu OHSAWA ,  Satoshi SEO ,  Takao HAMADA

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

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1059 ,  C09K2211/185 ,  H01L51/5016 ,  H05B33/14

Abstract: A novel phosphorescent organometallic iridium complex is provided in which a coordination position of a ligand with respect to a metal can be controlled in synthesis. A novel phosphorescent organometallic iridium complex is provided which can keep high quantum efficiency and can emit phosphorescence in the blue to green wavelength region. A phosphorescent organometallic iridium complex which includes a structure represented by General Formula (G1) and whose ligand is a 4H-1,2,4-triazole compound which has an unsubstituted phenyl group at the 3-position, a substituted or unsubstituted phenyl group at the 4-position, and a phenyl group at the 5-position. In the phenyl group at the 5-position, an alkyl group is bonded to at least one of the ortho-positions, and the other of the ortho-positions, the meta-positions, and the para-position are substituted or unsubstituted.

公开(公告)号：US20160190479A1

公开(公告)日：2016-06-30

申请号：US14976244

申请日：2015-12-21

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Tomoka HARA ,  Hideko INOUE ,  Tatsuyoshi TAKAHASHI ,  Takao HAMADA ,  Satoshi SEO

IPC: H01L51/00 ,  C07D403/14 ,  C07D409/10 ,  C09K11/02 ,  C09K11/06

CPC classification number: H01L51/0072 ,  C07D403/14 ,  C07D409/10 ,  C09K11/025 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1044 ,  C09K2211/185 ,  H01L51/0059 ,  H01L51/0074 ,  H01L51/0085 ,  H01L51/5016 ,  H01L2251/5384

Abstract: The organic compound represented by Formula G1 below has a structure in which the 2-position of a dibenzoquinazoline ring is directly, or via one or more arylene groups, bonded to a skeleton with a hole-transport property. In the formula, n represents any of 0 to 3, m represents 1 or 2, A represents a single bond, or a substituted or unsubstituted arylene group having 6 to 13 carbon atoms, B represents a ring having a substituted or unsubstituted dibenzofuran skeleton, a substituted or unsubstituted dibenzothiophene skeleton, or a substituted or unsubstituted carbazole skeleton, and each of R1 to R14 independently 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 7 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 13 carbon atoms.

Abstract translation: 下述通式G1表示的有机化合物具有二苯并喹唑啉环的2位直接或通过一个或多个亚芳基键合到具有空穴传输性的骨架的结构。 在该式中，n表示0〜3中的任一个，m表示1或2，A表示单键，或取代或未取代的碳原子数6〜13的亚芳基，B表示具有取代或未取代的二苯并呋喃骨架的环， 取代或未取代的二苯并噻吩骨架或取代或未取代的咔唑骨架，R 1〜R 14各自独立地表示氢，取代或未取代的碳原子数1〜6的烷基，取代或未取代的环烷基，具有5〜7个 碳原子和取代或未取代的碳原子数为6〜13的芳基。

公开(公告)号：US20160190471A1

公开(公告)日：2016-06-30

申请号：US14976443

申请日：2015-12-21

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko INOUE ,  Yui YAMADA ,  Tsunenori SUZUKI ,  Satoshi SEO

IPC: H01L51/00 ,  C07D401/14

CPC classification number: H01L51/0067 ,  C07D401/14 ,  C09K11/06 ,  H01L51/0054 ,  H01L51/0058 ,  H01L51/006

Abstract: An object is to provide an organic compound having high heat resistance and a light-emitting element, a light-emitting device, an electronic device, and a display device each having high reliability. Provided are an organic compound having a 2,2′-(pyridine-2,6-diyl)bipyrimidine skeleton in which the 2-positions of pyrimidine skeletons are bonded to the 2- and 6-positions of a pyridine skeleton, and having a structure in which at least one aryl group having a fused structure with 10 to 16 carbon atoms is bonded to the 2,2′-(pyridine-2,6-diyl)bipyrimidine skeleton, and a light-emitting element, a light-emitting device, an electronic device, and a display device each containing the organic compound.

Abstract translation: 本发明的目的是提供一种具有高耐热性的有机化合物和具有高可靠性的发光元件，发光装置，电子设备和显示装置。 提供了具有2,2' - （吡啶-2,6-二基）联嘧啶骨架的有机化合物，其中嘧啶骨架的2-位与吡啶骨架的2-和6-位键合，并且具有 其中至少一个具有10至16个碳原子的稠合结构的芳基与2,2' - （吡啶-2,6-二基）联嘧啶骨架结合，发光元件，发光 装置，电子装置以及各自含有有机化合物的显示装置。

公开(公告)号：US20160118606A1

公开(公告)日：2016-04-28

申请号：US14924114

申请日：2015-10-27

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko INOUE ,  Tomoya YAMAGUCHI ,  Satoshi SEO ,  Yui YAMADA

IPC: H01L51/00 ,  C09K11/06 ,  H01L27/32 ,  C07F15/00

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1044 ,  C09K2211/1088 ,  C09K2211/185 ,  H01L51/0025 ,  H01L51/5016 ,  H01L2251/5384

Abstract: A high-purity organometallic iridium complex is provided. The organometallic iridium complex includes iridium and a plurality of ligands cyclometallated to the iridium. Each of the plurality of ligands includes a heteroaromatic ring having a coordinatable nitrogen atom. In LC analysis of the organometallic iridium complex, an impurity which has a monochlorinated ligand among the plurality of ligands is 0.1% or less by quantitating using peak area count with a PDA detector.

Abstract translation: 提供高纯度有机金属铱络合物。 有机金属铱络合物包括铱和多个与铱环金属化的配位体。 多个配体中的每一个包括具有可配位的氮原子的杂芳环。 在有机金属铱络合物的LC分析中，通过使用PDA检测器的峰面积计数定量，多个配体中具有一氯化配体的杂质为0.1％以下。

公开(公告)号：US20160093818A1

公开(公告)日：2016-03-31

申请号：US14867535

申请日：2015-09-28

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko INOUE ,  Tomoya YAMAGUCHI

IPC: H01L51/00 ,  C09K11/06 ,  H01L27/32 ,  C07F15/00

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C09K11/06 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/1088 ,  C09K2211/1092 ,  C09K2211/185 ,  H01L51/5016

Abstract: An organometallic complex emitting light with high color purity. The organometallic complex is represented by General Formula (G1). In General Formula (G1), L represents a monoanionic ligand; R1 represents a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms or a substituted or unsubstituted aryl group having 6 to 13 carbon atoms; each of R2 to R5 independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group; the organometallic complex is monosubstituted, disubstituted, trisubstituted, tetrasubstituted, or unsubstituted by the R5; X represents O, S, or Se; and M represents a metal belonging to Group 9 or 10. When M represents a metal belonging to Group 9, in is 3 and n is 1, 2, or 3. When M represents a metal belonging to Group 10, m is 2 and n is 1 or 2.

Abstract translation: 有色金属配合物发出高纯度的光。 有机金属络合物由通式（G1）表示。 在通式（G1）中，L表示单阴离子配体; R1表示取代或未取代的碳原子数1〜10的烷基或碳原子数6〜13的取代或未取代的芳基。 R 2至R 5各自独立地表示氢，取代或未取代的具有1至6个碳原子的烷基，或取代或未取代的苯基; 有机金属配合物被R5单取代，双取代，四取代或未被取代; X表示O，S或Se; M表示属于9或10族的金属。当M表示属于9族的金属时，in为3，n为1,2或3.当M表示属于第10族的金属时，m为2，n 是1或2。

公开(公告)号：US20150376217A1

公开(公告)日：2015-12-31

申请号：US14846181

申请日：2015-09-04

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko INOUE ,  Tomoya YAMAGUCHI ,  Hiromi SEO ,  Satoshi SEO ,  Kunihiko SUZUKI ,  Miki KANAMOTO

IPC: C07F15/00 ,  H01L51/00

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C09K11/025 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1044 ,  C09K2211/1059 ,  C09K2211/185 ,  H01L51/0058 ,  H01L51/006 ,  H01L51/0074 ,  H01L51/5016 ,  H05B33/10

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.

Abstract translation: 作为具有新骨架的新型物质，提供了通过减少发射光谱的半宽度而实现提高的色纯度的发光效率高的有机金属络合物。 本发明的一个实施方案是一种有机金属配合物，其中包括二个或更多个氮原子（包括作为配位原子的氮原子）的六酮和六元杂芳环是配体。 在通式（G1）中，X表示包括两个或更多个氮原子的取代或未取代的六元杂芳环，包括作为配位原子的氮原子。 此外，R 1〜R 4各自表示取代或未取代的碳原子数1〜6的烷基。

公开(公告)号：US20150073144A1

公开(公告)日：2015-03-12

申请号：US14539377

申请日：2014-11-12

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko INOUE ,  Tomoka NAKAGAWA ,  Tomoya YAMAGUCHI ,  Hiromi SEO ,  Satoshi SEO

IPC: H01L51/00

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C09K11/06 ,  C09K2211/185 ,  H01L51/0067 ,  H01L51/5016 ,  H05B33/14

Abstract: As a novel substance having a novel skeleton, provided is a novel phosphorescent organometallic iridium complex that can emit phosphorescence in a blue green to red wavelength region and has high emission efficiency. The phosphorescent organometallic iridium complex has a ligand having a pyridyl pyrimidine skeleton, i.e., the phosphorescent organometallic iridium complex has a ligand having a structure represented by the following general formula (G0). Note that in the formula, R1 and R4 to R6 separately represent hydrogen or an alkyl group having 1 to 6 carbon atoms; and R2 and R3 separately represent any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a phenyl group that may have a substituent, and a pyridyl group that may have a substituent.

Abstract translation: 作为具有新骨架的新物质，提供了可以在蓝绿色至红色波长区域发射磷光体并具有高发光效率的新型磷光有机金属铱络合物。 磷光有机金属铱络合物具有具有吡啶基嘧啶骨架的配体，即磷光有机金属铱络合物具有由以下通式（G0）表示的结构的配体。 注意，在该式中，R 1和R 4至R 6分别表示氢或具有1至6个碳原子的烷基; R2和R3分别表示氢原子，碳原子数为1〜6的烷基，可以具有取代基的苯基，以及可具有取代基的吡啶基。

公开(公告)号：US20150021579A1

公开(公告)日：2015-01-22

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: H01L51/50 ,  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：US20140339526A1

公开(公告)日：2014-11-20

申请号：US14278775

申请日：2014-05-15

Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.

Inventor： Hideko INOUE ,  Tomoya YAMAGUCHI ,  Hiromi SEO ,  Tatsuyoshi TAKAHASHI ,  Satoshi SEO

IPC: H01L51/00

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1029 ,  C09K2211/1044 ,  C09K2211/185 ,  H01L51/006 ,  H01L51/0061 ,  H01L51/0072 ,  H01L51/5016

Abstract: A light-emitting element including a phosphorescent organometallic complex is provided. The organometallic complex emits phosphorescence in the yellow green to orange wavelength range and has high emission efficiency and high reliability. Thus, the organometallic complex that exhibits phosphorescence is provided. The organometallic complex, in which nitrogen at the 3-position of a pyrimidine ring is coordinated to a metal, a carbazole skeleton is bonded to the 4-position of the pyrimidine ring, and the carbazole skeleton is bonded to the metal, is used as an emission center. The metal is preferably a Group 9 element or a Group 10 element, more preferably iridium.

Abstract translation: 提供了包含磷光有机金属络合物的发光元件。 有机金属络合物在黄绿色至橙色波长范围内发射磷光体，发射效率高，可靠性高。 因此，提供了表现出磷光的有机金属络合物。 将嘧啶环3位上的氮与金属配位的有机金属配合物，咔唑骨架与嘧啶环的4位键合，咔唑骨架与金属键合，作为 排放中心。 金属优选为9族元素或10族元素，更优选为铱。

公开(公告)号：US20140256934A1

公开(公告)日：2014-09-11

申请号：US14286219

申请日：2014-05-23

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko INOUE ,  Tomoka NAKAGAWA ,  Satoshi SEO

IPC: H01L51/00

CPC classification number: H01L51/0085 ,  C07F15/0033

Abstract: Provided is a novel organometallic complex which can be synthesized easily and emits phosphorescence, or a compound which emits red phosphorescence. The inventors focused on easy synthesis of an m-aminophenyl pyrazine derivative represented by the following general formula (G0), synthesized an organometallic complex having a structure in which the derivative is coordinated to a Group 9 or Group 10 metal ion, and further synthesized a useful substance which emits red phosphorescence.

Abstract translation: 提供了可以容易地合成并发射磷光的新颖的有机金属配合物，或发出红色磷光的化合物。 本发明人着重于简单合成由以下通式（G0）表示的间氨基苯基吡嗪衍生物，合成具有其衍生物与第9族或第10族金属离子配位的结构的有机金属络合物，并进一步合成 发出红色磷光的有用物质。