JP2016540727A - 電子素子のための材料としてのトリアリールアミン置換ベンゾ[h]キノリン誘導体 - Google Patents
電子素子のための材料としてのトリアリールアミン置換ベンゾ[h]キノリン誘導体 Download PDFInfo
- Publication number
- JP2016540727A JP2016540727A JP2016520074A JP2016520074A JP2016540727A JP 2016540727 A JP2016540727 A JP 2016540727A JP 2016520074 A JP2016520074 A JP 2016520074A JP 2016520074 A JP2016520074 A JP 2016520074A JP 2016540727 A JP2016540727 A JP 2016540727A
- Authority
- JP
- Japan
- Prior art keywords
- groups
- compound
- group
- organic
- aromatic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 0 CCC(C)*(*(C)C1)C1(C)[Al](*)N(C)[Al]* Chemical compound CCC(C)*(*(C)C1)C1(C)[Al](*)N(C)[Al]* 0.000 description 6
- DXSIFZLOUITCRR-UHFFFAOYSA-N CC1(C)c(cc(C)cc2)c2-c2ccccc12 Chemical compound CC1(C)c(cc(C)cc2)c2-c2ccccc12 DXSIFZLOUITCRR-UHFFFAOYSA-N 0.000 description 2
- HDBWAWNLGGMZRQ-UHFFFAOYSA-N C=Cc(cc1)ccc1-c1ccccc1 Chemical compound C=Cc(cc1)ccc1-c1ccccc1 HDBWAWNLGGMZRQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
Description
Aは、*印の結合を介して結合する式(A−1)および(A−2)の基から選ばれ;
Ar2は、出現毎に同一であるか異なり、1以上のR1基により置換されてよい5〜24個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;
Xは、出現毎に同一であるか異なり、単結合またはBR2、C(R2)2、-C(R2)2-C(R2)2-、C(R2)2=C(R2)2-、-C(R2)2-O-、-C(R2)2-NR2-、Si(R2)2、C=O、NR2、PR2、P(=O)R2、O、S、S=OおよびSO2から選ばれる基であり;
R1、R2は、出現毎に同一であるか異なり、H、D、F、C(=O)R3、CN、Si(R3)3、N(R3)2、P(=O)(R3)2、OR3、S(=O)R3、S(=O)2R3、1〜20個の炭素原子を有する直鎖アルキルもしくはアルコキシ基、3〜20個の炭素原子を有する分岐あるいは環状アルキルもしくはアルコキシ基、2〜20個の炭素原子を有するアルケニルもしくはアルキニル基(ここで、上記言及した基は、夫々1以上のR3基により置換されてよく、上記言及した基中の1以上のCH2基は、-R3C=CR3-、-C≡C-、Si(R3)2、C=O、C=NR3、-C(=O)O-、-C(=O)NR3-、NR3、P(=O)(R3)、-O-、-S-、SOもしくはSO2で置き代えられてよい。)または、1以上のR3基により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;ここで、2個以上のR1もしくR2基は、たがいに結合し、環を形成してよく;
R3は、出現毎に同一であるか異なり、H、D、F、C(=O)R4、CN、Si(R4)3、N(R4)2、P(=O)(R4)2、OR4、S(=O)R4、S(=O)2R4、1〜20個の炭素原子を有する直鎖アルキルもしくはアルコキシ基、3〜20個の炭素原子を有する分岐あるいは環状アルキルもしくはアルコキシ基、2〜20個の炭素原子を有するアルケニルもしくはアルキニル基(ここで、上記言及した基は、夫々1以上のR4基により置換されてよく、上記言及した基中の1以上のCH2基は、-R4C=CR4-、-C≡C-、Si(R4)2、C=O、C=NR4、-C(=O)O-、-C(=O)NR4-、NR4、P(=O)(R4)、-O-、-S-、SOもしくはSO2で置き代えられてよい。)または、1以上のR4基により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;ここで、2個以上のR3基は、たがいに結合し、環を形成してよく;
R4は、出現毎に同一であるか異なり、H、D、F、CN、1〜20個の炭素原子を有する脂肪族、芳香族もしくは複素環式芳香族有機基であって、ここで、1以上の水素原子は、D、FもしくはCNで置き代えられてよく;2個以上のR4置換基は、たがいに結合し、環を形成してよく;
nは、0、1、2または3であり;
iは、出現毎に同一であるか異なり、0または1であり;および
中央に描かれたNをもつベンゼン環において、一以上の環メンバー-CR1=は、各場合に、-N=により置き代えられてよい。
(A)スズキ重合;
(B)ヤマモト重合;
(C)スチル重合および
(D)ハートウイッグ-ブッフバルト重合
重合をこれらの方法により実行することができる方法と次いでポリマーを反応媒体から分離し、精製することができる方法は、当業者に知られており、文献、たとえば、WO 2003/048225、WO 2004/037887およびWO 2004/037887に詳細に記載されている。
−アノード
−正孔注入層
−正孔輸送層
−随意に、1、2または3個のさらなる正孔輸送層
−発光層
−電子輸送層
−電子注入層
−カソード。
言及した層の全てが必ずしも存在する必要がないことおよび/またはさらなる層が追加的に存在してもよい。
以下の例は、本発明を説明する役目を行う。これらを限定として解釈すべきではない。
出発化合物10-ブロモベンゾ[h]キノリンは文献から知られている(CAS番号[152583-10-3])。さらなる出発化合物としての、対応するN-ヘテロ環誘導体は、CAS[66693-82-1]により知られている。
(4-ベンゾ[h]キノリン-10-イルフェニル)ビフェニル-4-イル(9,9-ジメチル-9H-フルオレン-2-イル)アミン
(4-ベンゾ[h]キノリン-10-イルフェニル)ビフェニル-4-イル(9,9-ジメチル-9H-フルオレン-2-イル)アミン
10-ベンゾ[h]キノリン-10-イル-12,12-ジメチル-10,12-ジヒドロ-10-アザインデノ[2,1-b]フルオレン
本発明のOLEDと先行技術のOLEDが、WO 04/058911にしたがう一般的プロセスにより製造されるが、ここに記載される状況(層の厚さの変化、材料)に適合される。
緑色の燐光参照素子C1を製造し、本発明の素子I1およびI2と比較した。電流密度2mA/cm2における参照素子C1は、外部量子効率11.7%と、寿命(10000cd/m2におけるLD80)90時間とを有する。比較によって、本発明の素子I1は15.5%のより良好な量子効率と、120時間のより良好な、10000cd/m2におけるLD80とを有する。本発明の素子I2は、15.8%の量子効率と、100時間の寿命とを有する。
緑色の燐光参照素子C1を製造し、本発明の素子I3〜I6と比較した。電流密度2mA/cm2における参照素子C1は、外部量子効率11.7%を有する。比較によって、本発明の素子I3〜I6は、13.3%(I3)、14.2%(I4)、13.7%(I5)、12.8%(I6)のより良好な量子効率を有する。
Claims (18)
- 式(I)の化合物;
Aは、*印の結合を介して結合する式(A−1)および(A−2)の基から選ばれ;
Ar2は、出現毎に同一であるか異なり、1以上のR1基により置換されてよい5〜24個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;
Xは、出現毎に同一であるか異なり、単結合またはBR2、C(R2)2、-C(R2)2-C(R2)2-、C(R2)2=C(R2)2-、-C(R2)2-O-、-C(R2)2-NR2-、Si(R2)2、C=O、NR2、PR2、P(=O)R2、O、S、S=OおよびSO2から選ばれる基であり;
R1、R2は、出現毎に同一であるか異なり、H、D、F、C(=O)R3、CN、Si(R3)3、N(R3)2、P(=O)(R3)2、OR3、S(=O)R3、S(=O)2R3、1〜20個の炭素原子を有する直鎖アルキルもしくはアルコキシ基、3〜20個の炭素原子を有する分岐あるいは環状アルキルもしくはアルコキシ基、2〜20個の炭素原子を有するアルケニルもしくはアルキニル基(ここで、上記言及した基は、夫々1以上のR3基により置換されてよく、上記言及した基中の1以上のCH2基は、-R3C=CR3-、-C≡C-、Si(R3)2、C=O、C=NR3、-C(=O)O-、-C(=O)NR3-、NR3、P(=O)(R3)、-O-、-S-、SOもしくはSO2で置き代えられてよい。)または、1以上のR3基により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;ここで、2個以上のR1もしくR2基は、たがいに結合し、環を形成してよく;
R3は、出現毎に同一であるか異なり、H、D、F、C(=O)R4、CN、Si(R4)3、N(R4)2、P(=O)(R4)2、OR4、S(=O)R4、S(=O)2R4、1〜20個の炭素原子を有する直鎖アルキルもしくはアルコキシ基、3〜20個の炭素原子を有する分岐あるいは環状アルキルもしくはアルコキシ基、2〜20個の炭素原子を有するアルケニルもしくはアルキニル基(ここで、上記言及した基は、夫々1以上のR4基により置換されてよく、上記言及した基中の1以上のCH2基は、-R4C=CR4-、-C≡C-、Si(R4)2、C=O、C=NR4、-C(=O)O-、-C(=O)NR4-、NR4、P(=O)(R4)、-O-、-S-、SOもしくはSO2で置き代えられてよい。)または、1以上のR4基により置換されてよい5〜30個の芳香族環原子を有する芳香族もしくは複素環式芳香族環構造であり;ここで、2個以上のR3基は、たがいに結合し、環を形成してよく;
R4は、出現毎に同一であるか異なり、H、D、F、CN、1〜20個の炭素原子を有する脂肪族、芳香族もしくは複素環式芳香族有機基であって、1以上の水素原子は、D、FもしくはCNで置き代えられてよく;2個以上のR4置換基は、たがいに結合し、環を形成してよく;
nは、0、1、2または3であり;
iは、出現毎に同一であるか異なり、0または1であり;および
中央に描かれたNをもつベンゼン環において、一以上の環メンバー-CR1=は、各場合に、-N=により置き代えられてよい。 - 中央に描かれたNをもつベンゼン環において、0個または丁度1個もしくは2個の環メンバー-CR1=は、-N=により置き代えられていることを特徴とする、請求項1記載の化合物。
- 中央に描かれたNをもつ式(I)中の全3個のベンゼン環において、環メンバー-CR1=は、-N=により置き代えられていないことを特徴とする、請求項1または2記載の化合物。
- nが、0であることを特徴とする、請求項1〜3何れか1項記載の化合物。
- Ar1は、出現毎に同一であるか異なり、1以上のR1基により置換されてよいベンゼン、ピリジン、ピリミジン、トリアジン、ナフタレン、キノリン、フルオレン、スピロビフルオレン、インデノフルオレン、カルバゾール、インデノカルバゾール、インドロカルバゾール、ジベンゾフランおよびジベンゾチオフェンから選ばれることを特徴とする、請求項1〜4何れか1項記載の化合物。
- 式(A−2)の基に対して、0個、丁度1個もしくは丁度2個の添え字iは、1であり、その他の添え字iは、0であることを特徴とする、請求項1〜5何れか1項記載の化合物。
- Xは、出現毎に同一であるか異なり、単結合またはC(R2)2、C=O、NR2、OおよびSから選ばれる基であることを特徴とする、請求項1〜6何れか1項記載の化合物。
- Ar2は、出現毎に同一であるか異なり、各々1以上のR1基により置換されてよいベンゼン、ビフェニル、テルフェニル、クアテルフェニル、ピリジン、ピリミジン、ピラジン、ピリダジン、トリアジン、ナフタレン、キノリン、フルオレン、スピロビフルオレン、インデノフルオレン、カルバゾール、インデノカルバゾール、インドロカルバゾール、ジベンゾフランおよびジベンゾチオフェンから選ばれることを特徴とする、請求項1〜7何れか1項記載の化合物。
- 置換基R1、R2、R3およびR4として、14個を超える芳香族環原子を有する縮合アリールもしくはヘテロアリール基を含まないことを特徴とする請求項1〜8何れか1項記載の化合物。
- A基に加えて、任意のさらなるアリールアミノ基、任意のさらなる架橋されたアリールアミノ基または任意のさらなるカルバゾール基を含まないことを特徴とする請求項1〜9何れか1項記載の化合物。
- ポリマー、オリゴマーまたはデンドリマーへの結合が、式(I)中でR1またはR2により置換されている任意の所望の位置に位置してよい、請求項1〜11何れか1項記載の一以上の化合物を含むオリゴマー、ポリマーまたはデンドリマー。
- 請求項1〜11何れか1項記載の少なくとも一つの化合物と少なくとも一つの溶媒とを含む調合物。
- 請求項1〜11何れか1項記載の化合物の、電子素子での使用。
- アノード、カソードと少なくとも一つの有機層を含み、有機層が請求項1〜11何れか1項記載の少なくとも一つの化合物を含む電子素子。
- 有機集積回路、有機電界効果トランジスタ、有機薄膜トランジスタ、有機発光トランジスタ、有機太陽電池、有機光学検査器、有機光受容器、有機電場消光素子、発光電子化学電池、有機レーザーダイオードおよび有機エレクトロルミネッセンス素子から選ばれることを特徴とする請求項16記載の電子素子。
- 請求項1〜11何れか1項記載の化合物が、発光層中でマトリックス材料として、または正孔輸送層中で正孔輸送材料として存在することを特徴とする請求項17記載の有機エレクトロルミッセンス素子。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP13004785.5 | 2013-10-04 | ||
EP13004785 | 2013-10-04 | ||
PCT/EP2014/002416 WO2015049022A1 (de) | 2013-10-04 | 2014-09-05 | Triarylamin-substituierte benzo[h]chinolin-derivate als materialien für elektronische vorrichtungen |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2016540727A true JP2016540727A (ja) | 2016-12-28 |
JP6498667B2 JP6498667B2 (ja) | 2019-04-10 |
Family
ID=49303693
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2016520074A Expired - Fee Related JP6498667B2 (ja) | 2013-10-04 | 2014-09-05 | 電子素子のための材料としてのトリアリールアミン置換ベンゾ[h]キノリン誘導体 |
Country Status (6)
Country | Link |
---|---|
US (1) | US10407394B2 (ja) |
EP (1) | EP3052477B1 (ja) |
JP (1) | JP6498667B2 (ja) |
KR (1) | KR102299572B1 (ja) |
CN (1) | CN105593213B (ja) |
WO (1) | WO2015049022A1 (ja) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9859517B2 (en) * | 2012-09-07 | 2018-01-02 | Nitto Denko Corporation | White organic light-emitting diode |
KR102120894B1 (ko) * | 2013-05-03 | 2020-06-10 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102269288B1 (ko) * | 2013-08-29 | 2021-06-25 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 헤테로 고리 화합물, 발광 소자, 발광 장치, 전자 장치, 및 조명 장치 |
JP2015227328A (ja) * | 2014-05-02 | 2015-12-17 | 株式会社半導体エネルギー研究所 | 化合物、発光素子、発光装置、電子機器、及び照明装置 |
KR102424977B1 (ko) | 2015-04-14 | 2022-07-26 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
KR102630644B1 (ko) | 2015-12-17 | 2024-01-30 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
KR102643638B1 (ko) * | 2016-09-13 | 2024-03-06 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
US20220384732A1 (en) * | 2018-07-09 | 2022-12-01 | Merck Patent Gmbh | Materials for electronic devices |
KR20200143089A (ko) * | 2019-06-14 | 2020-12-23 | 삼성전자주식회사 | 유기 센서 및 전자 장치 |
US11691971B2 (en) | 2020-06-19 | 2023-07-04 | Incyte Corporation | Naphthyridinone compounds as JAK2 V617F inhibitors |
US11753413B2 (en) | 2020-06-19 | 2023-09-12 | Incyte Corporation | Substituted pyrrolo[2,1-f][1,2,4]triazine compounds as JAK2 V617F inhibitors |
MX2023000056A (es) | 2020-07-02 | 2023-04-12 | Incyte Corp | Compuestos tricíclicos de urea como inhibidores de la variante v617f de la cinasa de janus 2 (jak2 v617f). |
WO2022006456A1 (en) | 2020-07-02 | 2022-01-06 | Incyte Corporation | Tricyclic pyridone compounds as jak2 v617f inhibitors |
US11661422B2 (en) | 2020-08-27 | 2023-05-30 | Incyte Corporation | Tricyclic urea compounds as JAK2 V617F inhibitors |
WO2022140231A1 (en) | 2020-12-21 | 2022-06-30 | Incyte Corporation | Deazaguaine compounds as jak2 v617f inhibitors |
KR20220121283A (ko) * | 2021-02-24 | 2022-09-01 | 엘티소재주식회사 | 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조 방법 및 유기물층용 조성물 |
TW202302589A (zh) | 2021-02-25 | 2023-01-16 | 美商英塞特公司 | 作為jak2 v617f抑制劑之螺環內醯胺 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003282270A (ja) * | 2002-03-25 | 2003-10-03 | Konica Corp | 有機エレクトロルミネッセンス素子及びそれを用いた表示装置 |
JP2009246097A (ja) * | 2008-03-31 | 2009-10-22 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、表示装置、及び照明装置 |
JP2010505241A (ja) * | 2006-09-14 | 2010-02-18 | チバ ホールディング インコーポレーテッド | 複素環式架橋ビフェニルおよびそれらのoledにおける使用 |
JP2012503600A (ja) * | 2008-09-24 | 2012-02-09 | エルジー・ケム・リミテッド | 新規なアントラセン誘導体およびこれを用いた有機電子素子 |
WO2012095143A1 (de) * | 2011-01-13 | 2012-07-19 | Merck Patent Gmbh | Verbindungen für organische elektrolumineszenzvorrichtungen |
JP2013001707A (ja) * | 2011-06-16 | 2013-01-07 | Samsung Display Co Ltd | 縮合環化合物及びそれを含む有機発光素子 |
JP2013065842A (ja) * | 2011-08-30 | 2013-04-11 | Semiconductor Energy Lab Co Ltd | 複素環化合物、発光素子、発光装置、電子機器及び照明装置 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4790260B2 (ja) * | 2004-12-22 | 2011-10-12 | 出光興産株式会社 | アントラセン誘導体を用いた有機エレクトロルミネッセンス素子 |
JP4972938B2 (ja) * | 2006-01-12 | 2012-07-11 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
KR101888658B1 (ko) * | 2011-04-15 | 2018-08-14 | 에스에프씨 주식회사 | 신규한 화합물 및 이를 포함하는 유기전계발광소자 |
KR101722027B1 (ko) * | 2012-05-03 | 2017-04-03 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함한 유기 발광 소자 |
KR102120894B1 (ko) * | 2013-05-03 | 2020-06-10 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
US9537106B2 (en) * | 2013-05-09 | 2017-01-03 | Universal Display Corporation | Organic electroluminescent materials and devices |
-
2014
- 2014-09-05 KR KR1020167011835A patent/KR102299572B1/ko active IP Right Grant
- 2014-09-05 EP EP14761793.0A patent/EP3052477B1/de active Active
- 2014-09-05 JP JP2016520074A patent/JP6498667B2/ja not_active Expired - Fee Related
- 2014-09-05 US US15/026,650 patent/US10407394B2/en active Active
- 2014-09-05 CN CN201480054649.XA patent/CN105593213B/zh active Active
- 2014-09-05 WO PCT/EP2014/002416 patent/WO2015049022A1/de active Application Filing
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003282270A (ja) * | 2002-03-25 | 2003-10-03 | Konica Corp | 有機エレクトロルミネッセンス素子及びそれを用いた表示装置 |
JP2010505241A (ja) * | 2006-09-14 | 2010-02-18 | チバ ホールディング インコーポレーテッド | 複素環式架橋ビフェニルおよびそれらのoledにおける使用 |
JP2009246097A (ja) * | 2008-03-31 | 2009-10-22 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、表示装置、及び照明装置 |
JP2012503600A (ja) * | 2008-09-24 | 2012-02-09 | エルジー・ケム・リミテッド | 新規なアントラセン誘導体およびこれを用いた有機電子素子 |
WO2012095143A1 (de) * | 2011-01-13 | 2012-07-19 | Merck Patent Gmbh | Verbindungen für organische elektrolumineszenzvorrichtungen |
JP2013001707A (ja) * | 2011-06-16 | 2013-01-07 | Samsung Display Co Ltd | 縮合環化合物及びそれを含む有機発光素子 |
JP2013065842A (ja) * | 2011-08-30 | 2013-04-11 | Semiconductor Energy Lab Co Ltd | 複素環化合物、発光素子、発光装置、電子機器及び照明装置 |
Also Published As
Publication number | Publication date |
---|---|
CN105593213B (zh) | 2019-02-05 |
EP3052477B1 (de) | 2018-10-24 |
KR20160065199A (ko) | 2016-06-08 |
US10407394B2 (en) | 2019-09-10 |
JP6498667B2 (ja) | 2019-04-10 |
KR102299572B1 (ko) | 2021-09-07 |
US20160214942A1 (en) | 2016-07-28 |
EP3052477A1 (de) | 2016-08-10 |
WO2015049022A1 (de) | 2015-04-09 |
CN105593213A (zh) | 2016-05-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6585211B2 (ja) | 電子素子のための材料 | |
JP6698099B2 (ja) | 有機エレクトロルミネッセンス素子のための材料 | |
JP6498667B2 (ja) | 電子素子のための材料としてのトリアリールアミン置換ベンゾ[h]キノリン誘導体 | |
JP6591433B2 (ja) | 電子素子のための材料 | |
KR102602818B1 (ko) | 6,9,15,18-테트라히드로-s-인다세노[1,2-b:5,6-b']디플루오렌 유도체 및 전자 소자에서의 이의 용도 | |
JP6567520B2 (ja) | 電子素子のための材料 | |
JP6608451B2 (ja) | 電子素子のための材料 | |
JP6749999B2 (ja) | 電子素子のための材料 | |
JP6419802B2 (ja) | 電子素子のための材料 | |
JP6495259B2 (ja) | 電子素子のための材料 | |
JP6367229B2 (ja) | 電子素子のための化合物 | |
JP6370800B2 (ja) | 電子素子のための材料 | |
JP6407883B2 (ja) | 電子素子のための材料 | |
JP2018507909A (ja) | 電子素子のための材料 | |
JP2018531893A (ja) | 有機エレクトロルミネッセンス素子のためのフェノキサジン誘導体 | |
JP2018526360A (ja) | 有機エレクトロルミネッセンス素子のためのフェノキサジン誘導体 | |
JP2017513855A (ja) | 電子素子のための材料 | |
KR20200128705A (ko) | 유기 전계 발광 디바이스용 재료 | |
KR102626977B1 (ko) | 전자 디바이스용 재료 | |
JP6469673B2 (ja) | 電子素子のための材料 | |
JP2020510615A (ja) | 有機エレクトロルミネッセンス素子(oled)の材料としてのビスベンゾフラン縮合2,8−ジアミノインデノ[1,2−b]フルオレン誘導体およびその関連化合物 | |
JP2019523246A (ja) | 有機エレクトロルミネッセンス素子のための材料 | |
JP2019507138A (ja) | 電子素子のための材料 | |
TW202019861A (zh) | 用於有機電致發光裝置的材料 | |
KR20200051722A (ko) | 전자 디바이스용 재료 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20170904 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20180605 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20180531 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20180905 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20190212 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20190313 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6498667 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
LAPS | Cancellation because of no payment of annual fees |