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公开(公告)号：US20230348400A1
公开(公告)日：2023-11-02
申请号：US18305609
申请日：2023-04-24
Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Inventor： Takuya HARUYAMA , Sachiko KAWAKAMI , Yui YOSHIYASU , Nobuharu OHSAWA , Takeyoshi WATABE , Hideko YOSHIZUMI
CPC classification number: C07D239/70 , C07F1/08 , C07F7/0812 , C07F15/0033 , H10K85/342 , H10K85/371 , H10K85/40 , H10K85/633 , H10K85/655 , C07B2200/05
Abstract: A novel organic compound is provided. The organic compound is represented by General Formula (G1). In General Formula (G1), R1 to R16 each independently represent any one of hydrogen (including deuterium), a substituted or unsubstituted straight-chain alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted branched alkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl group having 4 to 10 carbon atoms and having a bridged structure, a trialkylsilyl group having 3 to 12 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; at least one of R1 to R16 represents a substituent represented by General Formula (g1-1); and one or more, preferably two or more of R1 to R16 in General Formula (G1) represent substituents other than hydrogen (including deuterium) and the substituent represented by General Formula (g1-1).
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22.发明公开公开(公告)号：US20230329083A1
公开(公告)日：2023-10-12
申请号：US18025112
申请日：2021-08-30
Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Inventor： Yui YOSHIYASU , Masatoshi TAKABATAKE , Hideko YOSHIZUMI , Yuta KAWANO , Takeyoshi WATABE , Satoshi SEO
CPC classification number: H10K85/342 , C07F15/0033 , C09K11/06 , H10K50/11
Abstract: A novel organometallic complex with high heat resistance is provided. The organometallic complex includes a structure represented by General Formula (G1) below, in which iridium and a ligand are included, the ligand includes a pyrazine skeleton, iridium is bonded to nitrogen at the 1-position of the pyrazine skeleton, an aryl group including a cyano group as a substituent is bonded at the 5-position of the pyrazine skeleton, and each of the 3-position and the 6-position of the pyrazine skeleton is independently bonded to any one of hydrogen, an alkyl group, and an alkoxy group.
(In the formula, A represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms. In addition, Ar represents an aryl group having 6 to 25 carbon atoms and at least one cyano group as a substituent. Each of R1 and R2 independently represents any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, and an alkoxy group having 1 to 6 carbon atoms.)-
公开(公告)号：US20230282772A1
公开(公告)日：2023-09-07
申请号：US18112788
申请日：2023-02-22
Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Inventor： Satoshi SEO , Nobuharu OHSAWA , Hideko YOSHIZUMI
Abstract: To provide a light-emitting device with high emission efficiency and high reliability. A light-emitting layer of the light-emitting device includes a first substance emitting light from a doublet excited state based on f-d transition and a second substance that is a fluorescent substance. The longest-wavelength absorption edge among absorption edges in the absorption spectrum of the first substance is positioned at a wavelength shorter than the wavelength of the longest-wavelength absorption edge among absorption edges in the absorption spectrum of the second substance. The first substance has a short exciton lifetime and high exciton generation efficiency, and efficient energy transfer occurs between the first substance and the second substance; thus, the light-emitting device can have high emission efficiency and high reliability.
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24.发明公开公开(公告)号：US20230203054A1
公开(公告)日：2023-06-29
申请号：US18068575
申请日：2022-12-20
Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Inventor： Sachiko KAWAKAMI , Yuki HAYASHI , Miyako MORIKUBO , Tomohiro KUBOTA , Hiromitsu KIDO , Tomoya YAMAGUCHI , Hideko YOSHIZUMI , Satoshi SEO
IPC: C07D491/048 , H10K10/46 , H10K85/60
CPC classification number: C07D491/048 , H10K10/46 , H10K85/6572 , H10K85/6574 , H10K85/657
Abstract: An organic compound with a long lifetime and high emission efficiency is provided. An organic compound represented by General Formula (G1) is provided. In the formula, any one of X1 to X4 represents N, another one represents C, and the others represent C or N. Any one of C is bonded to a group represented by General Formula (r1), and the others are bonded to hydrogen (H), an alkyl (R) group, a cycloalkyl (Cy) group, an aryl (Ar) group, or a heteroaryl (Het) group. Ar1 represents an aromatic hydrocarbon, and is fused to an adjacent ring at a given site. When Ar1 represents a benzene ring, the benzene ring includes an Ar group or a Het group. Q and Z represent O or S. Any of R31 to R34 represents a bond to any one of X1 to X4, and the others represent H, an R group, a Cy group, an Ar group, or a Het group. Any one of R35 to R38 represents a polycyclic ring aromatic hydrocarbon group or a Het group, and the others represent H, an R group, a Cy group, an Ar group, or a Het group.
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25.发明公开公开(公告)号：US20230143281A1
公开(公告)日：2023-05-11
申请号：US17910103
申请日：2021-03-15
Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Inventor： Yui YOSHIYASU , Akira NAGASAKA , Hideko YOSHIZUMI , Toshiki SASAKI , Satoshi SEO
CPC classification number: H01L51/0074 , H01L51/0071 , H01L51/0073 , H01L51/0072 , H01L51/0054 , H01L51/5012
Abstract: A composition for a light-emitting device is provided. The composition is formed by mixing a first organic compound having a benzofuropyrimidine skeleton, and a second organic compound represented by General Formula (Q1):
R1 to R14 each independently represent hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted monocyclic saturated hydrocarbon having 5 to 7 carbon atoms in a ring, a substituted or unsubstituted polycyclic saturated hydrocarbon having 7 to 10 carbon atoms in a ring, a substituted or unsubstituted aryl group having 6 to 13 carbon atoms in a ring, or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms in a ring. Furthermore, β1 and β2 each represent any of an unsubstituted β-naphthyl group, an unsubstituted biphenyl group, and an unsubstituted terphenyl group, and at least one of β1 and β2 is an unsubstituted β-naphthyl group.-
Patent Agency Ranking
26.发明申请公开(公告)号：US20210336156A1
公开(公告)日：2021-10-28
申请号：US17263674
申请日：2019-07-29
Applicant: Semiconductor Energy Laboratory Co., Ltd.
Inventor： Yui Yoshiyasu , Hideko YOSHIZUMI , Takeyoshi WATABE , Satoshi SEO
Abstract: A novel organometallic complex is provided. One embodiment of the present invention provides a novel organometallic complex having a high quantum yield. An Ir complex has a structure including a 1H-naphtho[1,2-d]imidazole skeleton as a ligand and being represented by General Formula (G-1) below. Of Ns included in the 1H-naphtho[1,2-d]imidazole skeleton, N that is not bonded to Ir is bonded to a substituted or unsubstituted aryl group. In General Formula (G-1), each of R1 to R10 independently represents any of hydrogen, an alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 7 carbon atoms, a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, and an electron-withdrawing group, and Ar represents a substituted or unsubstituted aryl group having 6 to 25 carbon atoms.
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公开(公告)号：US20210320267A1
公开(公告)日：2021-10-14
申请号：US17264456
申请日：2019-09-17
Applicant: Semiconductor Energy Laboratory Co., Ltd.
Inventor： Satoshi SEO , Tomoya YAMAGUCHI , Hideko YOSHIZUMI , Takeyoshi WATABE
IPC: H01L51/00
Abstract: The emission efficiency of a light-emitting device that emits near-infrared light is increased. The reliability of a light-emitting device that emits near-infrared light is increased. A light-emitting device using an organic compound that emits light having a maximum peak wavelength greater than or equal to 760 nm and less than or equal to 900 nm is provided. An organometallic complex represented by General Formula (G1) is provided. In the formula, each of R1 to R11 independently represents hydrogen or an alkyl group having 1 to 6 carbon atoms; at least two of R1 to R4 and at least two of R5 to R9 represent an alkyl group having 1 to 6 carbon atoms; X represents a substituted or unsubstituted benzene ring or naphthalene ring; n is 2 or 3; and L represents a monoanionic ligand.
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公开(公告)号：US20210214381A1
公开(公告)日：2021-07-15
申请号：US17137941
申请日：2020-12-30
Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Inventor： Tomoya YAMAGUCHI , Hideko YOSHIZUMI , Yuta KAWANO , Takeyoshi WATABE , Satoshi SEO
Abstract: Providing a novel organometallic complex represented by Structure Formula (G1). A1 to A4 independently represent an alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms. R1 to R5 independently represent any one of hydrogen, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, and a cyano group, wherein at least one of R1 to R5 represents a cyano group. R11 to R14 independently represent an alkyl group having 2 to 6 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms. R15 and R16 independently represent any one of hydrogen, a methyl group, and an ethyl group. Note that R11 and R12 may be bonded to each other to form a ring, and R13 and R14 may be bonded to each other to form a ring.
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29.发明申请公开(公告)号：US20250151617A1
公开(公告)日：2025-05-08
申请号：US19018216
申请日：2025-01-13
Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Inventor： Miki KURIHARA , Hideko YOSHIZUMI , Satomi WATABE , Hiromitsu KIDO , Satoshi SEO
IPC: H10K85/60 , C07D491/048 , H10K50/11 , H10K59/12 , H10K71/16
Abstract: A novel organic compound is provided. That is, a novel organic compound that is effective in improving reliability of a light-emitting element is provided. The organic compound includes a condensed ring including a pyrimidine ring and is represented by General Formula (G1). In General Formula (G1), A represents a group having 6 to 100 carbon atoms and includes at least one of an aromatic ring and a heteroaromatic ring. The aromatic ring and the heteroaromatic ring may each include a substituent. Furthermore, Q represents oxygen or sulfur. A ring X represents a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted phenanthrene ring.
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公开(公告)号：US20240276877A1
公开(公告)日：2024-08-15
申请号：US18422060
申请日：2024-01-25
Applicant: SEMICONDUCTOR ENERGY LABORATORY CO., LTD.
Inventor： Hideko YOSHIZUMI , Nobuharu OHSAWA
IPC: H10K85/60 , H10K50/11 , H10K59/121 , H10K101/30
CPC classification number: H10K85/6572 , H10K50/11 , H10K59/1216 , H10K85/636 , H10K2101/30
Abstract: The light-emitting device includes a first electrode, a second electrode, a first unit between the first electrode and the second electrode, and a first layer between the second electrode and the first unit. The first unit contains a first light-emitting material. The first layer includes a second layer and a third layer. The second layer is positioned between the third layer and the first unit. The second layer contains a first organic compound and a second organic compound. The first organic compound has an acid dissociation constant pKa larger than or equal to 8. The second organic compound includes no pyridine ring, no phenanthroline ring, or one phenanthroline ring. The third layer contains a material having a spin density higher than or equal to 1×1018 spins/cm3 observed by electron spin resonance spectroscopy when the material is in a film state.
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