[go: up one dir, main page]

CN109354588A - 一种以含氮五元杂环为核心的有机电致发光化合物及其应用 - Google Patents

一种以含氮五元杂环为核心的有机电致发光化合物及其应用 Download PDF

Info

Publication number
CN109354588A
CN109354588A CN201811171335.4A CN201811171335A CN109354588A CN 109354588 A CN109354588 A CN 109354588A CN 201811171335 A CN201811171335 A CN 201811171335A CN 109354588 A CN109354588 A CN 109354588A
Authority
CN
China
Prior art keywords
compound
core
nitrogenous
molar ratio
ring heterocycles
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
Application number
CN201811171335.4A
Other languages
English (en)
Other versions
CN109354588B (zh
Inventor
王立春
唐丹丹
张兆超
李崇
张小庆
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jiangsu Sunera Technology Co Ltd
Original Assignee
Jiangsu Sanyue Optoelectronic Technology Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Jiangsu Sanyue Optoelectronic Technology Co Ltd filed Critical Jiangsu Sanyue Optoelectronic Technology Co Ltd
Priority to CN201811171335.4A priority Critical patent/CN109354588B/zh
Publication of CN109354588A publication Critical patent/CN109354588A/zh
Application granted granted Critical
Publication of CN109354588B publication Critical patent/CN109354588B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero 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
    • C07D401/14—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
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 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
    • C07D405/14—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
    • 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
    • C07D413/10—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 linked by a carbon chain containing aromatic rings
    • 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
    • C07D417/10—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 linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D421/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms
    • C07D421/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings
    • C07D421/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having selenium, tellurium, or halogen atoms as ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D497/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—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
    • C09K11/06—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]
    • H10K50/11—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
    • H10K85/60—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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • 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
    • 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
    • C09K2211/1007—Non-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
    • C09K2211/1003—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
    • C09K2211/1025—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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/104—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with other 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
    • C09K2211/1044—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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms 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
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms 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
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three 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
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three 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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen 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
    • C09K2211/10—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
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

本发明公开了一种以含氮五元杂环为核心的有机电致发光化合物及其应用，该化合物以含氮五元杂环为核心，具有分子间不易结晶、不易聚集、具有良好成膜性的特点。将本发明化合物作为发光层材料应用于有机电致发光器件上，应用本发明化合物的有机电致发光器件具有良好的光电性能表现，可以更好的适应和满足面板制造企业的应用要求。

Description

一种以含氮五元杂环为核心的有机电致发光化合物及其应用
技术领域
本发明涉及半导体技术领域，尤其是涉及一种含氮五元杂环为核心的化合物，以及其作为发光层材料在有机发光二极管上的应用。
背景技术
有机电致发光(OLED:Organic Light Emission Diodes)器件技术既可以用来制造新型显示产品，也可以用于制作新型照明产品，有望替代现有的液晶显示和荧光灯照明，应用前景十分广泛。
OLED发光器件犹如三明治的结构，包括电极材料膜层，以及夹在不同电极膜层之间的有机功能材料，各种不同功能材料根据用途相互叠加在一起共同组成OLED发光器件。作为电流器件，当对OLED发光器件的两端电极施加电压，并通过电场作用有机层功能材料膜层中的正负电荷，正负电荷进一步在发光层中复合，即产生OLED电致发光。
有机发光二极管(OLEDs)在大面积平板显示和照明方面的应用引起了工业界和学术界的广泛关注。然而，传统有机荧光材料只能利用电激发形成的25％单线态激子发光，器件的内量子效率较低(最高为25％)。外量子效率普遍低于5％，与磷光器件的效率还有很大差距。尽管磷光材料由于重原子中心强的自旋-轨道耦合增强了系间窜越，可以有效利用电激发形成的单线态激子和三线态激子发光，使器件的内量子效率达100％。但磷光材料存在价格昂贵，材料稳定性较差，器件效率滚落严重等问题限制了其在OLEDs的应用。热激活延迟荧光(TADF)材料是继有机荧光材料和有机磷光材料之后发展的第三代有机发光材料。该类材料一般具有小的单线态-三线态能级差(△EST)，三线态激子可以通过反系间窜越转变成单线态激子发光。这可以充分利用电激发下形成的单线态激子和三线态激子，器件的内量子效率可以达到100％。同时，材料结构可控，性质稳定，价格便宜无需贵重金属，在OLEDs领域的应用前景广阔。
虽然理论上TADF材料可以实现100％的激子利用率，但实际上存在如下问题:(1)设计分子的T1和S1态具有强的CT特征，非常小的S1-T1态能隙，虽然可以通过TADF过程实现高T1→S1态激子转化率，但同时导致低的S1态辐射跃迁速率，因此，难于兼具(或同时实现)高激子利用率和高荧光辐射效率；(2)即使已经采用掺杂器件减轻T激子浓度猝灭效应，大多数TADF材料的器件在高电流密度下效率滚降严重。
就当前OLED显示照明产业的实际需求而言，目前OLED材料的发展还远远不够，落后于面板制造企业的要求，作为材料企业开发更高性能的有机功能材料显得尤为重要。
发明内容
针对现有技术存在的上述问题，本申请人提供了一种以含氮五元杂环为核心的化合物及其在有机电致发光器件上的应用。本发明化合物基于TADF机理以含氮五元杂环为核心，作为发光层材料应用于有机发光二极管，本发明制作的器件具有良好的光电性能，能够满足面板制造企业的要求。
本发明的技术方案如下：
本申请人提供了一种以含氮五元杂环为核心的化合物，该化合物结构如通式(1)所示：
通式(1)中，X表示为氧原子、硫原子、硒原子、C1-10直链或支链烷基取代的亚烷基、芳基取代的亚烷基、烷基或芳基取代的叔胺基中的一种；
通式(1)中，Ar表示苯基、联苯基、萘基、蒽基、菲基、芘基、呋喃基、噻吩基或吡啶基；
通式(1)中，R1、R2分别独立的表示为氢原子或通式(3)所示结构；且R1与R2不同时为氢原子；
R4、R5分别独立的表示为C1-10直链或支链烷基、苯基、萘基、联苯基、通式(6)、通式(7)、通式(8)或通式(9)所示结构；
其中，X5为氧原子、硫原子、C1-10直链或支链烷基取代的亚烷基、芳基取代的亚烷基、烷基或芳基取代的叔胺基中的一种；
R6、R7分别独立的表示苯基、萘基、二联苯基、三联苯基、二苯并呋喃、二苯并噻吩、9,9-二甲基芴或咔唑。
优选的，所述R1、R2表示为：
中的任一种。优选的，所述化合物的具体结构式为：
中的任一种。
本申请人还提供了一种制备所述化合物的方法，制备过程中发生的反应方程式是：
当R1为氢原子时，
具体制备方法为：
称取以含氮五元杂环为核心的溴代化合物和R2-H，用甲苯溶解；再加入Pd2(dba)3、三叔丁基膦、叔丁醇钠；在惰性气氛下，将上述反应物的混合溶液于反应温度95～110℃，反应10～24小时，冷却并过滤反应溶液，滤液旋蒸，过硅胶柱，得到目标产物；
所述以含氮五元杂环为核心的溴代化合物与R2-H的摩尔比为1:1.0～1.5，Pd2(dba)3与以含氮五元杂环为核心的溴代化合物的摩尔比为0.006～0.02:1，三叔丁基膦与以含氮五元杂环为核心的溴代化合物的摩尔比为0.006～0.02:1，叔丁醇钠与以含氮五元杂环为核心的溴代化合物的摩尔比为2.0～3.0:1；
当R1不为氢原子且R1和R2相同时，
具体制备方法为：
称取以含氮五元杂环为核心的溴代化合物和R1-H或R2-H，用甲苯溶解；再加入Pd2(dba)3、三叔丁基膦、叔丁醇钠；在惰性气氛下，将上述反应物的混合溶液于反应温度95～110℃，反应10～24小时，冷却并过滤反应溶液，滤液旋蒸，过硅胶柱，得到目标产物；
所述以含氮五元杂环为核心的溴代化合物与R1-H或R2-H的摩尔比为1:2.0～3.0，Pd2(dba)3与以含氮五元杂环为核心的溴代化合物的摩尔比为0.006～0.02:1，三叔丁基膦与以含氮五元杂环为核心的溴代化合物的摩尔比为0.006～0.02:1，叔丁醇钠与以含氮五元杂环为核心的溴代化合物的摩尔比为3.0～5.0:1；
当R1不为氢原子且当R1和R2不同时，
具体制备方法为：
称取以含氮五元杂环为核心的卤代化合物和R2-H，用甲苯溶解；再加入CuCl、1,10-邻菲啰啉、氢氧化钾；在惰性气氛下，将上述反应物的混合溶液于反应温度100～140℃，反应8～20小时，反应结束后加入1mol/L稀盐酸中和，混合液采用二氯甲烷萃取，有机相分别用氨水及水洗涤，旋蒸，过硅胶柱，得到中间产物；
所述以含氮五元杂环为核心的卤代化合物与R2-H的摩尔比为1:1.0～1.5，CuCl与以含氮五元杂环为核心的卤代化合物的摩尔比为0.05～0.15:1，1,10-邻菲啰啉与以含氮五元杂环为核心的卤代化合物的摩尔比为0.05～0.15:1，氢氧化钾与以含氮五元杂环为核心的卤代化合物的摩尔比为3.0～5.0:1；
称取中间产物和R1-H，用甲苯溶解；再加入Pd2(dba)3、三叔丁基膦、叔丁醇钠；在惰性气氛下，将上述反应物的混合溶液于反应温度95～110℃，反应10～24小时，冷却并过滤反应溶液，滤液旋蒸，过硅胶柱，得到目标产物；
所述中间产物与R1-H的摩尔比为1:1.0～1.5，Pd2(dba)3与中间产物的摩尔比为0.006～0.02:1，三叔丁基膦与中间产物的摩尔比为0.006～0.02:1，叔丁醇钠与中间产物的摩尔比为2.0～3.0:1。
本申请人还提供了一种包含所述化合物的发光器件，所述化合物作为发光层材料，用于制作OLED器件。
本发明有益的技术效果在于：
本发明化合物是一种发光材料，该类材料具有分子间不易结晶、不易聚集、具有良好成膜性的特点，本发明化合物分子中的刚性基团可以提高材料的热稳定性，所述化合物结构分子内包含电子给体(donor,D)与电子受体(acceptor,A)的组合可以增加轨道重叠、提高发光效率，同时连接芳香杂环基团以获得HOMO、LUMO空间分离的电荷转移态材料，实现小的S1态和T1态的能级差，从而在热刺激条件下实现反向系间窜越，适合作为发光层主体材料使用。进一步的，根据材料分子设计的不同，此类化合物也可以作为发光层材料的掺杂材料使用。
本发明化合物作为OLED发光器件的发光层主体材料使用时，器件的电流效率，功率效率和外量子效率均得到很大改善；同时对于器件寿命提升非常明显。
本发明所述化合物材料在OLED发光器件中具有良好的应用效果，具有良好的产业化前景。
附图说明
图1为本发明化合物应用的器件结构示意图；
其中，1为透明基板层，2为ITO阳极层，3为空穴注入层，4为空穴传输层，5为发光层，6为电子传输层，7为电子注入层，8为阴极反射电极层。
具体实施方式
下面结合附图和实施例，对本发明进行具体描述。
实施例9：化合物114的合成：
合成路线：
实施例11：化合物157的合成：
合成路线：
在250ml的三口瓶中，通氮气保护下，加入0.01mol3-(4-溴苯基)-4,5-二苯基-4H-1,2,4-三唑，0.012mol中间体H2，0.03mol叔丁醇钠，5×10-5molPd2(dba)3，5×10-5mol三叔丁基磷，150ml甲苯，加热回流24小时，取样点板，反应完全；自然冷却，过滤，滤液旋蒸，柱层析得到目标产物，HPLC纯度99.7％，收率65.9％；
元素分析结构(分子式C56H36N6)：理论值C,84.82；H,4.58；N,10.60；测试值：C,84.84；H,4.54；N,10.62。
元素分析结构(分子式C56H36N6)：理论值C,84.83；H,4.58；N,10.60；测试值：C,84.83；H,4.58；N,10.60。
HPLC-MS：材料分子量为792.93，实测分子量793.06。
实施例12：化合物187的合成：
合成路线：
在250ml的三口瓶中，通氮气保护下，加入0.01mol3-(4-溴苯基)-4,4-二甲基-5-苯基-4H-吡唑，0.012mol中间体H3，0.03mol叔丁醇钠，5×10-5molPd2(dba)3，5×10-5mol三叔丁基磷，150ml甲苯，加热回流24小时，取样点板，反应完全；自然冷却，过滤，滤液旋蒸，柱层析得到目标产物，HPLC纯度99.3％，收率73.4％；
元素分析结构(分子式C53H37N5O2)：理论值C,82.04；H,4.81；N,9.03；O,4.12；测试值：C,82.03；H,4.82；N,9.02；O,4.13。
HPLC-MS：材料分子量为775.89，实测分子量776.04。
实施例13：化合物190的合成：
合成路线：
化合物190的制备方法同实施例12，不同之处在于用中间体H4替换中间体H3。
元素分析结构(分子式C50H35N5O)：理论值C,83.19；H,4.89；N,9.70；O,2.22；测试值：C,83.18；H,4.91；N,9.71；O,2.20。
HPLC-MS：材料分子量为721.85，实测分子量722.04。
实施例14：化合物192的合成：
合成路线：
化合物192的制备方法同实施例12，不同之处在于用中间体H5替换中间体H3。
元素分析结构(分子式C68H53N5)：理论值C,86.87；H,5.68；N,7.45；测试值：C,86.86；H,5.68；N,7.46。
HPLC-MS：材料分子量为940.18，实测分子量940.35。
实施例15：化合物199的合成：
合成路线：
化合物199的制备方法同实施例12，不同之处在于用中间体H6替换中间体H3。
元素分析结构(分子式C59H49N5)：理论值C,85.58；H,5.96；N,8.46；测试值：C,85.60；H,5.95；N,8.45。
HPLC-MS：材料分子量为828.05，实测分子量828.47。
本发明化合物可以作为发光层材料使用，对本发明化合物157、现有材料CBP进行热性能、发光光谱及循环伏安稳定性的测试，测试结果如表1所示。
表1
化合物 Td(℃) λ<sub>PL</sub>(nm) 循环伏安稳定性
化合物157 418 372 优
材料CBP 353 369 差
注：热失重温度Td是在氮气气氛中失重1％的温度，在日本岛津公司的TGA-50H热重分析仪上进行测定，氮气流量为20mL/min；λPL是样品溶液荧光发射波长，利用日本拓普康SR-3分光辐射度计测定；循环伏安稳定性是通过循环伏安法观测材料的氧化还原特性来进行鉴定；测试条件：测试样品溶于体积比为2:1的二氯甲烷和乙腈混合溶剂，浓度1mg/mL，电解液是0.1M的四氟硼酸四丁基铵或六氟磷酸四丁基铵的有机溶液。参比电极是Ag/Ag+电极，对电极为钛板，工作电极为ITO电极，循环次数为20次。
由上表数据可知，本发明化合物具有较好的氧化还原稳定性，较高的热稳定性，合适的发光光谱，使得应用本发明化合物作为发光层材料的OLED器件效率和寿命得到提升。
以下通过实施例21～22和比较例2详细说明本发明合成的OLED材料在器件中作为发光层主体材料的应用效果。本发明所述22、比较例2与实施例21相比器件的制作工艺完全相同，并且所采用了相同的基板材料和电极材料，电极材料的膜厚也保持一致，所不同的是对器件中的发光层5的主体材料及掺杂材料做了变换。各实施例所得器件的结构组成如表2所示。所得器件的测试结果见表3所示。
实施例21
ITO阳极层2/空穴注入层3(三氧化钼MoO3，厚度10nm)/空穴传输层4(TAPC，厚度80nm)/发光层5(化合物GHN、化合物157和Ir(PPy)3按照40:60：10的重量比混掺，厚度30nm)/电子传输层6(TPBI，厚度40nm)/电子注入层7(LiF，厚度1nm)/Al。涉及到的材料结构式如下：
具体制备过程如下：
透明基板层1为透明基材，如透明PI膜、玻璃等。
对ITO阳极层2(膜厚为150nm)进行洗涤，即依次进行碱洗涤、纯水洗涤、干燥，再进行紫外线-臭氧洗涤以清除透明ITO表面的有机残留物。
在进行了上述洗涤之后的ITO阳极层2上，利用真空蒸镀装置，蒸镀膜厚为10nm的三氧化钼MoO3作为空穴注入层3使用。紧接着蒸镀80nm厚度的TAPC作为空穴传输层4。
上述空穴传输材料蒸镀结束后，制作OLED发光器件的发光层5，其结构包括OLED发光层5所使用化合物GHN、化合物157作为主体材料，Ir(PPy)3作为掺杂材料，化合物GHN、化合物157、Ir(PPy)3混掺重量比40:60:10，发光层膜厚为30nm。
在上述发光层5之后，继续真空蒸镀电子传输层材料为TPBI。该材料的真空蒸镀膜厚为40nm，此层为电子传输层6。
在电子传输层6上，通过真空蒸镀装置，制作膜厚为1nm的氟化锂(LiF)层，此层为电子注入层7。
在电子注入层7上，通过真空蒸镀装置，制作膜厚为80nm的铝(Al)层，此层为阴极反射电极层8使用。
如上所述地完成OLED发光器件后，用公知的驱动电路将阳极和阴极连接起来，测量器件的电流效率以及器件的寿命。所制作的OLED发光器件的测试结果见表3。
表2
表3
注：寿命测试系统为本发明所有权人与上海大学共同研究的OLED器件寿命测试仪。
实施例21～22为本发明所述化合物作为发光层Co-host材料搭配三嗪类主体材料应用于OLED发光器件制作；表3的测试结果表明：与比较例2相比；效率和寿命均获得较大改观，特别是器件的驱动寿命获得较大的提升。
从实施例所提供的测试数据来看，本发明化合物作为发光层材料在OLED发光器件中具有良好的应用效果，具有良好的产业化前景。
虽然已通过实施例和优选实施方式公开了本发明，但应理解，本发明不限于所公开的实施方式。相反，本领域技术人员应明白，其意在涵盖各种变型和类似的安排。因此，所附权利要求的范围应与最宽的解释相一致以涵盖所有这样的变型和类似的安排。

Claims (5)

1.一种以含氮五元杂环为核心的化合物，其特征在于该化合物结构如通式(1)所示：
通式(1)中，X表示为氧原子、硫原子、硒原子、C1-10直链或支链烷基取代的亚烷基、芳基取代的亚烷基、烷基或芳基取代的叔胺基中的一种；
通式(1)中，Ar表示苯基、联苯基、萘基、蒽基、菲基、芘基、呋喃基、噻吩基或吡啶基；
通式(1)中，R1、R2分别独立的表示为氢原子或通式(3)所示结构；且R1与R2不同时为氢原子；
R4、R5分别独立的表示为C1-10直链或支链烷基、苯基、萘基、联苯基、通式(6)、通式(7)、通式(8)或通式(9)所示结构；
其中，X5为氧原子、硫原子、C1-10直链或支链烷基取代的亚烷基、芳基取代的亚烷基、烷基或芳基取代的叔胺基中的一种；
R6、R7分别独立的表示苯基、萘基、二联苯基、三联苯基、二苯并呋喃、二苯并噻吩、9,9-二甲基芴或咔唑。
2.根据权利要求1所述的有机化合物，其特征在于所述R1、R2表示为：
中的任意一种。
3.根据权利要求1所述的化合物，其特征在于所述化合物的具体结构式为：
中的任一种。
4.一种制备权利要求1～3任一项所述化合物的方法，其特征在于制备过程中发生的反应方程式是：
当R1为氢原子时，
具体制备方法为：
称取以含氮五元杂环为核心的溴代化合物和R2-H，用甲苯溶解；再加入Pd2(dba)3、三叔丁基膦、叔丁醇钠；在惰性气氛下，将上述反应物的混合溶液于反应温度95～110℃，反应10～24小时，冷却并过滤反应溶液，滤液旋蒸，过硅胶柱，得到目标产物；
所述以含氮五元杂环为核心的溴代化合物与R2-H的摩尔比为1:1.0～1.5，Pd2(dba)3与以含氮五元杂环为核心的溴代化合物的摩尔比为0.006～0.02:1，三叔丁基膦与以含氮五元杂环为核心的溴代化合物的摩尔比为0.006～0.02:1，叔丁醇钠与以含氮五元杂环为核心的溴代化合物的摩尔比为2.0～3.0:1；
当R1不为氢原子且R1和R2相同时，
具体制备方法为：
称取以含氮五元杂环为核心的溴代化合物和R1-H或R2-H，用甲苯溶解；再加入Pd2(dba)3、三叔丁基膦、叔丁醇钠；在惰性气氛下，将上述反应物的混合溶液于反应温度95～110℃，反应10～24小时，冷却并过滤反应溶液，滤液旋蒸，过硅胶柱，得到目标产物；
所述以含氮五元杂环为核心的溴代化合物与R1-H或R2-H的摩尔比为1:2.0～3.0，Pd2(dba)3与以含氮五元杂环为核心的溴代化合物的摩尔比为0.006～0.02:1，三叔丁基膦与以含氮五元杂环为核心的溴代化合物的摩尔比为0.006～0.02:1，叔丁醇钠与以含氮五元杂环为核心的溴代化合物的摩尔比为3.0～5.0:1；
当R1不为氢原子且当R1和R2不同时，
具体制备方法为：
称取以含氮五元杂环为核心的卤代化合物和R2-H，用甲苯溶解；再加入CuCl、1,10-邻菲啰啉、氢氧化钾；在惰性气氛下，将上述反应物的混合溶液于反应温度100～140℃，反应8～20小时，反应结束后加入1mol/L稀盐酸中和，混合液采用二氯甲烷萃取，有机相分别用氨水及水洗涤，旋蒸，过硅胶柱，得到中间产物；
所述以含氮五元杂环为核心的卤代化合物与R2-H的摩尔比为1:1.0～1.5，CuCl与以含氮五元杂环为核心的卤代化合物的摩尔比为0.05～0.15:1，1,10-邻菲啰啉与以含氮五元杂环为核心的卤代化合物的摩尔比为0.05～0.15:1，氢氧化钾与以含氮五元杂环为核心的卤代化合物的摩尔比为3.0～5.0:1；
称取中间产物和R1-H，用甲苯溶解；再加入Pd2(dba)3、三叔丁基膦、叔丁醇钠；在惰性气氛下，将上述反应物的混合溶液于反应温度95～110℃，反应10～24小时，冷却并过滤反应溶液，滤液旋蒸，过硅胶柱，得到目标产物；
所述中间产物与R1-H的摩尔比为1:1.0～1.5，Pd2(dba)3与中间产物的摩尔比为0.006～0.02:1，三叔丁基膦与中间产物的摩尔比为0.006～0.02:1，叔丁醇钠与中间产物的摩尔比为2.0～3.0:1。
5.一种包含权利要求1～3任一项所述化合物的发光器件，其特征在于所述化合物作为发光层材料，用于制作OLED器件。
CN201811171335.4A 2016-08-19 2016-08-19 一种以含氮五元杂环为核心的有机电致发光化合物及其应用 Active CN109354588B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201811171335.4A CN109354588B (zh) 2016-08-19 2016-08-19 一种以含氮五元杂环为核心的有机电致发光化合物及其应用

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201610693680.9A CN106467518A (zh) 2016-08-19 2016-08-19 一种以含氮五元杂环为核心的有机电致发光化合物及其应用
CN201811171335.4A CN109354588B (zh) 2016-08-19 2016-08-19 一种以含氮五元杂环为核心的有机电致发光化合物及其应用

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CN201610693680.9A Division CN106467518A (zh) 2016-08-19 2016-08-19 一种以含氮五元杂环为核心的有机电致发光化合物及其应用

Publications (2)

Publication Number Publication Date
CN109354588A true CN109354588A (zh) 2019-02-19
CN109354588B CN109354588B (zh) 2021-04-27

Family

ID=58229940

Family Applications (2)

Application Number Title Priority Date Filing Date
CN201610693680.9A Pending CN106467518A (zh) 2016-08-19 2016-08-19 一种以含氮五元杂环为核心的有机电致发光化合物及其应用
CN201811171335.4A Active CN109354588B (zh) 2016-08-19 2016-08-19 一种以含氮五元杂环为核心的有机电致发光化合物及其应用

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CN201610693680.9A Pending CN106467518A (zh) 2016-08-19 2016-08-19 一种以含氮五元杂环为核心的有机电致发光化合物及其应用

Country Status (1)

Country Link
CN (2) CN106467518A (zh)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107556292A (zh) * 2017-09-22 2018-01-09 苏州大学 吖啶‑咔唑给体衍生物及其制备方法以及基于其的有机电致发光器件
CN109912575B (zh) * 2017-12-12 2020-07-28 中节能万润股份有限公司 一种以含氮五元杂环为核心的化合物及其在有机电致发光器件上的应用
CN109912609A (zh) * 2017-12-12 2019-06-21 江苏三月光电科技有限公司 一种以含氮五元杂环为母核的化合物及其在有机电致发光器件上的应用
CN109096279B (zh) * 2018-09-28 2020-11-03 武汉天马微电子有限公司 氮杂环化合物、显示面板以及显示装置
CN110698458A (zh) * 2019-10-30 2020-01-17 烟台显华化工科技有限公司 一种有机发光材料及其应用

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110102055A (ko) * 2010-03-10 2011-09-16 제일모직주식회사 유기광전소자용 화합물 및 이를 포함하는 유기광전소자
US20130292659A1 (en) * 2010-12-08 2013-11-07 Hyung-Sun Kim Compound for organic optoelectronic device, organic light emitting diode including the same, and display device including the organic light emitting diode
CN103468246A (zh) * 2013-09-04 2013-12-25 吉林奥来德光电材料股份有限公司 一种含1,2,4-三氮唑类的有机发光材料、其制备方法及其电致发光器件
TW201434832A (zh) * 2013-02-12 2014-09-16 Univ Kyushu Nat Univ Corp 化合物、發光材料及有機發光元件
KR20160087331A (ko) * 2015-01-13 2016-07-21 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
WO2016116485A1 (de) * 2015-01-20 2016-07-28 Cynora Gmbh Azole zur verwendung in optoelektronischen bauelementen

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101256205B1 (ko) * 2010-09-30 2013-04-19 (주)씨에스엘쏠라 유기발광화합물 및 이를 구비한 유기발광소자
CN105017041B (zh) * 2015-06-12 2017-09-29 北京科技大学 二苯并环庚烯酮衍生物及其制备和应用

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110102055A (ko) * 2010-03-10 2011-09-16 제일모직주식회사 유기광전소자용 화합물 및 이를 포함하는 유기광전소자
US20130292659A1 (en) * 2010-12-08 2013-11-07 Hyung-Sun Kim Compound for organic optoelectronic device, organic light emitting diode including the same, and display device including the organic light emitting diode
TW201434832A (zh) * 2013-02-12 2014-09-16 Univ Kyushu Nat Univ Corp 化合物、發光材料及有機發光元件
CN103468246A (zh) * 2013-09-04 2013-12-25 吉林奥来德光电材料股份有限公司 一种含1,2,4-三氮唑类的有机发光材料、其制备方法及其电致发光器件
KR20160087331A (ko) * 2015-01-13 2016-07-21 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
WO2016116485A1 (de) * 2015-01-20 2016-07-28 Cynora Gmbh Azole zur verwendung in optoelektronischen bauelementen

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
MAN-KIT LEUNG ET AL.: "Novel Ambipolar Orthogonal Donor_Acceptor Host for Blue Organic Light Emitting Diodes", 《ORGANIC LETTERS》 *

Also Published As

Publication number Publication date
CN109354588B (zh) 2021-04-27
CN106467518A (zh) 2017-03-01

Similar Documents

Publication Publication Date Title
CN106279203B (zh) 一种含酮和氮杂环的化合物及其在有机电致发光器件上的应用
CN106467523B (zh) 一种有机芳香化合物及其应用
CN106467549B (zh) 一种含有苯并咪唑的化合物及其在有机电致发光器件上的应用
CN107056748B (zh) 一种以三嗪和酮为核心的化合物及其在有机电致发光器件上的应用
CN106220649B (zh) 一种基于二芳基酮的化合物及其在有机电致发光器件上的应用
CN113527315B (zh) 一种电致发光材料及器件
CN106467529B (zh) 一种以9-芴酮为核心的有机电致发光材料及其应用
CN106220638A (zh) 一种基于氧杂蒽酮的化合物及其应用
CN106543205B (zh) 一种含有苯并咪唑的化合物及其在oled上的应用
CN106467485B (zh) 一种以9-芴酮为核心的化合物及其应用
CN106467484B (zh) 一种以9-芴酮为核心的化合物及其在oled器件上的应用
CN109354588B (zh) 一种以含氮五元杂环为核心的有机电致发光化合物及其应用
Zhan et al. Utilizing electroplex emission to achieve external quantum efficiency up to 18.1% in nondoped blue OLED
CN106397415A (zh) 一种基于氮杂苯的五元环取代化合物及其应用
CN109912564A (zh) 一种以氰基氮杂苯为核心的化合物及其在oled器件上的应用
CN117362298A (zh) 一种电致发光材料及器件
CN107043382A (zh) 一种以三嗪为核心的化合物及其在有机电致发光器件上的应用
CN106467524B (zh) 一种有机芳香化合物及其在有机电致发光器件上的应用
CN107021925B (zh) 一种以氮杂二苯并环庚酮为核心的化合物及其在oled上的应用
CN106699763A (zh) 一种以喹唑啉酮衍生物为核心的化合物及其应用
CN106467532B (zh) 一种以含氮五元杂环为核心的化合物及其在oled器件上的应用
CN106543071B (zh) 一种以二苯并庚烯酮为核心的化合物及其在oled上的应用
CN106467531B (zh) 一种以含氮五元杂环为核心的化合物及其应用
CN111943986B (zh) 一种含有多个稠合杂环结构配体的金属配合物
CN109575054A (zh) 一种含硼六元杂环衍生物及其在有机电致发光器件中的应用

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
TA01 Transfer of patent application right

Effective date of registration: 20200212

Address after: 264006 No. 11 Wuzhishan Road, Yantai economic and Technological Development Zone, Shandong

Applicant after: VALIANT Co.,Ltd.

Address before: 214112 Wuxi New District, Jiangsu, Xinzhou Road, No. 210

Applicant before: JIANGSU SUNERA TECHNOLOGY Co.,Ltd.

TA01 Transfer of patent application right
GR01 Patent grant
GR01 Patent grant
TR01 Transfer of patent right

Effective date of registration: 20211213

Address after: 214112 No.210 Xinzhou Road, Wuxi City, Jiangsu Province

Patentee after: Jiangsu March Technology Co., Ltd

Address before: 264006 No. 11 Wuzhishan Road, Yantai economic and Technological Development Zone, Shandong

Patentee before: VALIANT Co.,Ltd.

TR01 Transfer of patent right