公开(公告)号：US10230055B2

公开(公告)日：2019-03-12

申请号：US15256000

申请日：2016-09-02

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Miki Kanamoto ,  Takeyoshi Watabe ,  Hideko Inoue ,  Satoshi Seo ,  Satomi Mitsumori ,  Tatsuyoshi Takahashi

IPC: H01L51/50 ,  H01L51/00 ,  C07D491/048 ,  C07F15/00 ,  C09K11/06 ,  H01L27/32

Abstract: Provided is a novel compound or a light-emitting element with high emission efficiency. The provided novel compound includes a bicarbazole skeleton and a benzofuropyrimidine skeleton or a benzothienopyrimidine skeleton. The provided light-emitting element includes the compound.

公开(公告)号：US10170710B2

公开(公告)日：2019-01-01

申请号：US15156679

申请日：2016-05-17

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Yui Yamada ,  Hideko Inoue

IPC: C07F15/00 ,  H01L51/00 ,  C09K11/06 ,  H01L27/32 ,  H01L51/52 ,  C23C16/42 ,  C07D471/04 ,  H01L27/12 ,  H01L51/50

Abstract: Provided is an organometallic complex which emits light with a short wavelength and has high emission efficiency and high heat resistance. The organometallic complex includes a central metal; and a first ligand, a second ligand, a third ligand, and a fourth ligand which are coordinated to the central metal. The first ligand includes a triazole skeleton including nitrogen bonded to the central metal. The second ligand includes an indolo[3,2-b]carbazole skeleton whose 6-position is bonded to the central metal or a pyrido[2,3-b:6,5-b′]diindole skeleton whose 6-position is bonded to the central metal. The third ligand includes a benzene skeleton whose carbon is bonded to the central metal. The fourth ligand includes a pyridine skeleton whose nitrogen is bonded to the central metal or a benzene skeleton whose carbon is bonded to the central metal.

公开(公告)号：US20180337346A1

公开(公告)日：2018-11-22

申请号：US15988152

申请日：2018-05-24

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Satoshi Seo ,  Takao Hamada ,  Tatsuyoshi Takahashi ,  Yasushi Kitano ,  Hiroki Suzuzki ,  Hideko Inoue

IPC: H01L51/00 ,  C07D403/14

CPC classification number: H01L51/0072 ,  C07D403/14 ,  H01L51/006 ,  H01L51/0061 ,  H01L51/0085 ,  Y02P20/582

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：US10096786B2

公开(公告)日：2018-10-09

申请号：US14974142

申请日：2015-12-18

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Yui Yamada ,  Hideko Inoue ,  Hiromi Seo ,  Tatsuyoshi Takahashi

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

Abstract: To provide an organometallic complex with high emission efficiency and high heat resistance, which emits yellow green light. The organometallic complex includes a metal and a ligand which is a benzo[h]quinazoline skeleton including a condensed ring bonded to benzo[h]quinazoline through a carbon-carbon bond between the 5-position and the 6-position. The organometallic complex has a structure represented by General Formula (G1). In General Formula (G1), M represents a metal belonging to Group 9 or 10; each of R1 to R4 independently represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; and R5 represents hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. A ring X represents a substituted or unsubstituted six-membered aromatic ring formed with carbon or both carbon and nitrogen.

公开(公告)号：US09985223B2

公开(公告)日：2018-05-29

申请号：US14934566

申请日：2015-11-06

Applicant: Semiconductor Energy Laboratory Co., Ltd.

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

IPC: C01G55/00 ,  C07D239/24 ,  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.

公开(公告)号：US09972794B2

公开(公告)日：2018-05-15

申请号：US15341380

申请日：2016-11-02

Applicant: Semiconductor Energy Laboratory Co., Ltd.

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

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

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

Abstract: Disclosed is an organometallic complex capable of variable phosphorescence characteristics and yellow emission at high luminance. The organometallic complex has a structure represented by a formula (G1), where at least one of R4, R5, R6, and R7 is a phenoxy group, M is a Group 9 metal or a Group 10 metal, and n is 2 when the central metal M is a Group 9 element, or n is 1 when the central metal M is a Group 10 element.

公开(公告)号：US09923149B2

公开(公告)日：2018-03-20

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 ,  C07D239/26 ,  C07D251/24 ,  C09K11/06 ,  C07D239/00 ,  H01L51/50 ,  H01L27/32

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.

公开(公告)号：US09917261B2

公开(公告)日：2018-03-13

申请号：US14537230

申请日：2014-11-10

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Yui Yamada ,  Tsunenori Suzuki ,  Satoshi Seo

IPC: H01L51/00 ,  F21V23/04 ,  C09K11/06 ,  C07D405/14 ,  H01L51/50

CPC classification number: H01L51/0072 ,  C07D405/14 ,  C09K11/06 ,  H01L51/0067 ,  H01L51/0073 ,  H01L51/5072

Abstract: A novel organic compound is provided. Alternatively, an organic compound that can be used as an electron-transport material of a light-emitting element is provided. An organic compound in which heteroaromatic groups each including two pyridine rings are bonded to the 2- and 8-positions of dibenzofuran is provided. The organic compound is an organic compound that can be used as an electron-transport material of a light-emitting element.

公开(公告)号：US09843002B2

公开(公告)日：2017-12-12

申请号：US15332309

申请日：2016-10-24

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Tomoya Yamaguchi ,  Hideko Inoue ,  Tatsuyoshi Takahashi

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

CPC classification number: H01L51/0085 ,  C07F15/0033 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1044 ,  C09K2211/185 ,  H01L51/5012 ,  H01L51/5016 ,  H01L51/5056 ,  H01L51/5072 ,  H01L51/5088 ,  H01L51/5092

Abstract: A novel organometallic complex having high color purity is provided. The organometallic complex includes a structure which includes iridium and a ligand and is represented by a general formula (G1). The ligand includes a pyrido[2,3-b]indole skeleton and a pyrimidine skeleton bonded to the 3-position of the pyrido[2,3-b]indole skeleton. The 2-position of the pyrido[2,3-b]indole skeleton and the pyrimidine skeleton are each bonded to the iridium. In the general formula (G1), R1 to R9 each independently represent any of hydrogen, a substituted or unsubstituted alkyl group having 1 to 6 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.

公开(公告)号：US09825230B2

公开(公告)日：2017-11-21

申请号：US14688383

申请日：2015-04-16

Applicant: Semiconductor Energy Laboratory Co., Ltd.

Inventor： Hideko Inoue ,  Yasushi Kitano ,  Hiromi Seo ,  Tatsuyoshi Takahashi ,  Satoshi Seo

IPC: C07D241/38 ,  H01L51/00 ,  C09K11/06 ,  H01L51/50

CPC classification number: H01L51/0052 ,  C07D241/38 ,  C09K11/06 ,  C09K2211/1007 ,  C09K2211/1011 ,  C09K2211/1044 ,  H01L51/0072 ,  H01L51/5016 ,  H01L51/504

Abstract: A novel heterocyclic compound is provided. A novel heterocyclic compound that can be used for a light-emitting element is provided. A novel heterocyclic compound that can improve the reliability of a light-emitting element when used for a light-emitting element is provided. A light-emitting element, a light-emitting device, an electronic appliance, or a lighting device which includes the novel heterocyclic compound and is highly reliable is provided. One embodiment of the present invention is a heterocyclic compound represented by a general formula (G0). In the general formula (G0), A represents a dibenzo[f,h]quinoxalinyl group, B represents a substituted or unsubstituted fluorenyl group, and Ar represents a substituted or unsubstituted arylene group having 6 to 25 carbon atoms. A-Ar—B  (G0)