CN111925315B - Nitrogen-containing compound, organic electroluminescent element using same, and electronic device - Google Patents

Nitrogen-containing compound, organic electroluminescent element using same, and electronic device Download PDF

Info

Publication number
CN111925315B
CN111925315B CN202010798721.7A CN202010798721A CN111925315B CN 111925315 B CN111925315 B CN 111925315B CN 202010798721 A CN202010798721 A CN 202010798721A CN 111925315 B CN111925315 B CN 111925315B
Authority
CN
China
Prior art keywords
carbon atoms
group
ring
substituted
unsubstituted
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.)
Active
Application number
CN202010798721.7A
Other languages
Chinese (zh)
Other versions
CN111925315A (en
Inventor
郑奕奕
马天天
刘新颖
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.)
Shaanxi Lighte Optoelectronics Material Co Ltd
Original Assignee
Shaanxi Lighte Optoelectronics Material 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 Shaanxi Lighte Optoelectronics Material Co Ltd filed Critical Shaanxi Lighte Optoelectronics Material Co Ltd
Priority to PCT/CN2020/122273 priority Critical patent/WO2021203673A1/en
Publication of CN111925315A publication Critical patent/CN111925315A/en
Application granted granted Critical
Publication of CN111925315B publication Critical patent/CN111925315B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • 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
    • C07D401/14—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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D405/02—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
    • C07D405/14—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
    • C07D409/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D409/10—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 carbon chain containing aromatic 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
    • C07D409/14—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
    • C07D475/00—Heterocyclic compounds containing pteridine ring 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
    • 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
    • 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
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
    • 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
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • 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
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • 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
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • 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
    • 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
    • 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
    • C09K2211/1018—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
    • C09K2211/1044—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
    • 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

Abstract

The present invention provides a nitrogen-containing compound, an organic electroluminescent device and an electronic apparatus, the chemical structure of the organic compound of the present invention comprises a carbazole ring, and the organic compound can be used as a material of a light-emitting layer in an electroluminescent device, improve the efficiency of the organic electroluminescent device and increase the lifetime of the organic electroluminescent device.

Description

Nitrogen-containing compound, organic electroluminescent element using same, and electronic device
Technical Field
The invention belongs to the technical field of organic electroluminescent materials, and particularly relates to a nitrogen-containing compound, an organic electroluminescent device using the nitrogen-containing compound and an electronic device.
Background
Organic electroluminescent devices, such as Organic Light Emitting Diodes (OLEDs), typically include a cathode and an anode disposed opposite each other, and a functional layer disposed between the cathode and the anode. The functional layer is composed of a plurality of organic or inorganic film layers and generally comprises an organic light-emitting layer, a hole transport layer positioned between the organic light-emitting layer and an anode, and an electron transport layer positioned between the organic light-emitting layer and a cathode. When voltage is applied to the anode and the cathode, the two electrodes generate an electric field, electrons on the cathode side move to the electroluminescent layer under the action of the electric field, holes on the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state and release energy outwards, so that the electroluminescent layer emits light outwards.
In the prior art, CN104039778A et al disclose materials that can be used to prepare light emitting layers in organic electroluminescent devices. However, the existing organic electroluminescent materials still have the problems of short luminescent life and low luminescent efficiency. Therefore, there is a need to continue to develop new materials to further improve the lifetime and efficiency performance of organic electroluminescent devices.
Disclosure of Invention
The invention aims to provide an organic electroluminescent material with excellent performance, which can be used as a luminescent layer in an organic electroluminescent device.
In order to achieve the above object, the present invention provides a nitrogen-containing compound having a structural formula shown in chemical formula 1:
Figure BDA0002626325870000011
wherein the ring A is a fused aromatic ring with ring-forming carbon atoms of 10-14 or a fused heteroaromatic ring with ring-forming carbon atoms of 8-12, and the ring A is not a carbazole ring;
the ring B is a benzene ring, a fused aromatic ring with ring-forming carbon atoms of 10-14 or a fused heteroaromatic ring with ring-forming carbon atoms of 8-12;
the ring C is a benzene ring or a condensed aromatic ring with 10-14 ring-forming carbon atoms;
R1、R2、R3、R4the aryl group is the same or different and is independently selected from deuterium, a halogen group, a cyano group, a halogenated alkyl group with 1-12 carbon atoms, an alkenyl group with 2-10 carbon atoms, an alkynyl group with 2-10 carbon atoms, a cycloalkyl group with 3-12 carbon atoms, a heterocycloalkyl group with 2-10 carbon atoms, an alkoxy group with 1-12 carbon atoms, an alkylthio group with 1-12 carbon atoms, a trialkylsilyl group with 3-12 carbon atoms, an aryl group with 6-20 carbon atoms, a heteroaryl group with 3-20 carbon atoms, an aryloxy group with 6-20 carbon atoms, an arylthio group with 6-20 carbon atoms and an arylsilyl group with 6-18 carbon atoms;
n1represents a substituent R1Number of (2), n2Represents a substituent R2Number of (2), n3Represents a substituent R3Number of (2), n4Represents a substituent R4Number of (2), n1、n2、n3、n4Are the same or different from each other and are each independently selected from 0, 1,2, 3 or 4;
when n is1When greater than 1, any two of R1Same or different when n2When greater than 1, any two of R2The same or different; when n is3When greater than 1, any two of R3Same or different when n4When greater than 1, any two of R4The same or different;
w is selected from substituted or unsubstituted aryl with 6-40 carbon atoms and substituted or unsubstituted heteroaryl with 3-40 carbon atoms;
the substituents in W, which may be the same or different from each other, are each independently selected from the group consisting of: deuterium, a halogen group, a cyano group, an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, a heteroaralkyl group having 4 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms optionally substituted with 0, 1,2 or 3 substituents selected from deuterium, fluorine, chlorine, bromine, cyano and alkyl, a heteroaryl group having 3 to 30 carbon atoms optionally substituted with 0, 1,2 or 3 substituents selected from deuterium, fluorine, chlorine, bromine, cyano and alkyl, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, aryloxy group having 6 to 20 carbon atoms, arylthio group having 6 to 20 carbon atoms;
in the W, when two substituents are present on the same atom, optionally, the two substituents attached to the same atom are linked to each other to form a saturated or unsaturated 5-to 18-membered aliphatic ring or a 5-to 18-membered aromatic ring with the atom to which they are commonly attached.
According to a second aspect of the present application, there is provided an organic electroluminescent device comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the above-mentioned nitrogen-containing compound.
According to a third aspect of the present application, there is provided an electronic device comprising the organic electroluminescent device of the present application.
Among the compounds of the present application, adamantane spiro-fused fluorenyl group, which is a part of the core of a nitrogen-containing compound, has high rigidity and a first triplet level, and a carbazole ring conjugated to the fused fluorenyl group in the compound has good hole transport ability, so that the nitrogen-containing compound of the present application is suitable as a host material of a light-emitting layer in an organic electroluminescent device. The adamantyl and the fluorenyl are screwed together, so that the electron cloud density of a large plane conjugated structure can be greatly increased through a hyperconjugation effect, the hole mobility of the nitrogen-containing compound is enhanced, the transmission balance of holes and electrons in a light-emitting layer is promoted, and the efficiency performance of an organic electroluminescent device is improved. Moreover, the improvement of the hole transport performance of the nitrogen-containing compound can improve the recombination rate of electrons and holes in the organic light-emitting layer, reduce or avoid the electrons from passing through the organic light-emitting layer and being transported to the hole transport layer, further effectively protect the hole transport layer material from the impact of the electrons, and prolong the service life of the organic electroluminescent device. Moreover, the adamantyl group screwed on the fluorenyl group has large space volume and strong rigidity, so that the mutual acting force between large plane conjugated structures can be reduced, the pi-pi stacking between molecules can be reduced, the stacking degree between molecules can be adjusted, the nitrogen-containing compound can have a more stable amorphous state during film forming, the film forming property of the nitrogen-containing compound can be improved, and the service life of an organic electroluminescent device can be further prolonged.
Additional features and advantages of the present application will be described in detail in the detailed description which follows.
Drawings
The accompanying drawings, which are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate embodiments of the application and together with the description serve to explain the principles of the application and not to limit the application. In the drawings:
fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
The main device reference numbers in the figure are explained as follows:
100. an anode; 200. a cathode; 310. a hole injection layer; 321. a hole transport layer; 322. an electron blocking layer; 330. an organic light emitting layer; 340. an electron transport layer; 350. an electron injection layer; 400. an electronic device.
Detailed Description
The following detailed description of embodiments of the present application will be made with reference to the accompanying drawings. It should be understood that the detailed description and specific examples, while indicating the present application, are given by way of illustration and explanation only, and are not intended to limit the present application.
In the drawings, the thickness of regions and layers may be exaggerated for clarity. The same reference numerals denote the same or similar structures in the drawings, and thus detailed descriptions thereof will be omitted.
In the context of the present application, it is,
Figure BDA0002626325870000021
as used herein, the term "substituent" refers to a position bonded to another substituent or a bonding position.
In the present application, the number of carbon atoms of W means all the number of carbon atoms. For example, if W is selected from substituted aryl groups having 40 carbon atoms, then all carbon atoms of the aryl group and substituents thereon are 40; when W is a 9, 9-dimethylfluorenyl group, it is a substituted fluorenyl group having 15 carbon atoms, and W has 13 ring-forming carbon atoms.
In the present application, the number of carbon atoms of the substituted aryl or heteroaryl group in L and Ar means the total number of carbon atoms of the aryl or heteroaryl group and the substituents thereon, for example, the substituted aryl group having the number of carbon atoms of 18 means the total number of carbon atoms of the aryl group and the substituents is 18.
For example, 2, 4-diphenyl-1, 3, 5-triazinyl is a substituted heteroaryl group having 15 carbon atoms.
In the present specification, the expression "substituted or unsubstituted aryl group having 6 to 40 carbon atoms" and "substituted or unsubstituted aryl group having 6 to 40 carbon atoms" are the same, and both mean that the total number of carbon atoms of the aryl group and the substituents thereon is 6 to 40. Similarly, in the present specification, the expressions "substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms" and "substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms" are the same, and both mean that the total carbon number of the heteroaryl and the substituent thereon is 3 to 30.
In the present specification, the expressions "substituted or unsubstituted aryl group having 6 to 40 carbon atoms" and "substituted or unsubstituted aryl group having 6 to 40 carbon atoms" are the same and mean that the total number of carbon atoms of the aryl group and the substituents thereon is 6 to 40. Similarly, in the present specification, the expressions "substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms" and "substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms" are the same, and both mean that the total number of carbon atoms of the heteroaryl group and the substituents thereon is 3 to 30.
In the present application, when a specific definition is not otherwise provided, "hetero" means that at least 1 hetero atom of B, N, O, S, Se, Si, or P, etc. is included in one functional group and the remaining atoms are carbon and hydrogen. An unsubstituted alkyl group can be a "saturated alkyl group" without any double or triple bonds.
The descriptions used in this application that "… … independently" and "… … independently" and "… … independently selected from" are interchangeable and should be understood in a broad sense to mean that the particular items expressed between the same symbols do not interfere with each other in different groups or that the particular items expressed between the same symbols do not interfere with each other in the same groups. For example: in that
Figure BDA0002626325870000031
Wherein each q is independently 0, 1,2 or 3, and each R "is independently selected from the group consisting of hydrogen, fluoro, chloro" and has the meaning: the formula Q-1 represents that Q substituent groups R ' are arranged on a benzene ring, each R ' can be the same or different, and the options of each R ' are not influenced mutually; formula Q-2 represents biphenylEach benzene ring of the benzene ring has q substituent groups R ', the number q of the substituent groups of R' on the two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced mutually.
In this application, "optional" or "optionally" means that the subsequently described event or circumstance may, but need not, occur, and that the description includes instances where the event or circumstance occurs or does not. For example, "a heterocyclic group optionally substituted with an alkyl" means that an alkyl may, but need not, be present, and the description includes the scenario where the heterocyclic group is substituted with an alkyl and the scenario where the heterocyclic group is not substituted with an alkyl. "two substituents bonded to the same atom are bonded to each other to form a saturated or unsaturated 5-to 18-membered aliphatic ring or a 5-to 18-membered aromatic ring with the atom to which they are bonded together" means that the two substituents bonded to the same atom may be, but need not be, cyclic, including the case where they are bonded to each other to form a saturated or unsaturated 5-to 18-membered aliphatic ring or a 5-to 18-membered aromatic ring, and also including the case where they are present independently of each other.
In the present application, the term "substituted or unsubstituted" means either no substituent or substituted with one or more substituents. Such substituents include, but are not limited to, deuterium, halogen groups (F, Cl, Br), cyano, alkyl, alkenyl, alkynyl, haloalkyl, aryl, heteroaryl, aryloxy, arylthio, alkylamino, cycloalkyl, heterocyclyl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio.
In the present application, "alkyl" may include straight chain alkyl or branched alkyl. Alkyl groups may have 1 to 12 carbon atoms, and numerical ranges such as "1 to 12" refer herein to each integer in the given range; for example, "1 to 12 carbon atoms" refers to an alkyl group that may contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, 12 carbon atoms. The alkyl group can also be a medium size alkyl group having 1 to 10 carbon atoms. The alkyl group may also be a lower alkyl group having 1 to 6 carbon atoms. In still other embodimentsIn this case, the alkyl group contains 1 to 4 carbon atoms; in still other embodiments, the alkyl group contains 1 to 3 carbon atoms. The alkyl group may be optionally substituted with one or more substituents described herein. Examples of alkyl groups include, but are not limited to, methyl (Me, -CH)3) Ethyl group (Et, -CH)2CH3) N-propyl (n-Pr, -CH)2CH2CH3) Isopropyl group (i-Pr, -CH (CH)3)2) N-butyl (n-Bu, -CH)2CH2CH2CH3) Isobutyl (i-Bu, -CH)2CH(CH3)2) Sec-butyl (s-Bu, -CH (CH)3)CH2CH3) Tert-butyl (t-Bu, -C (CH)3)3) And the like. Further, the alkyl group may be substituted or unsubstituted.
In the present application, "alkenyl" refers to a hydrocarbon group comprising one or more double bonds in a straight or branched hydrocarbon chain. Alkenyl groups may be unsubstituted or substituted. An alkenyl group may have 2 to 12 carbon atoms, and whenever appearing herein, numerical ranges such as "2 to 12" refer to each integer in the given range; for example, "2 to 20 carbon atoms" refers to an alkenyl group that may contain 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, 12 carbon atoms. For example, the alkenyl group can be vinyl, butadiene, or 1,3, 5-hexatriene.
In this application, cycloalkyl refers to cyclic saturated hydrocarbons, including monocyclic and polycyclic structures. Cycloalkyl groups may have 3-12 carbon atoms, and numerical ranges such as "3 to 12" refer to each integer in the given range; for example, "3 to 12 carbon atoms" refers to a cycloalkyl group that may contain 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, 12 carbon atoms. Cycloalkyl groups can also be divided into monocyclic-only one ring, bicyclic-two rings-or polycyclic-three or more rings. Cycloalkyl groups can also be divided into spiro rings, fused rings, and bridged rings, in which two rings share a common carbon atom, and more than two rings share a common carbon atom. In addition, cycloalkyl groups may be substituted or unsubstituted. In some embodiments cycloalkyl is 5 to 10 membered cycloalkyl, in other embodiments cycloalkyl is 5 to 8 membered cycloalkyl, examples of which may be, but are not limited to: five-membered cycloalkyl, i.e., cyclopentyl, six-membered cycloalkyl, i.e., cyclohexyl, 10-membered polycycloalkyl, e.g., adamantyl, and the like.
In the present application, as a halogen group as a substituent, there is fluorine, chlorine, bromine or iodine.
In this application, "alkoxy" means an alkyl group attached to the rest of the molecule through an oxygen atom, wherein the alkyl group has the meaning as described herein. Unless otherwise specified, the alkoxy group contains 1 to 12 carbon atoms. In one embodiment, the alkoxy group contains 1 to 6 carbon atoms; in another embodiment, the alkoxy group contains 1 to 4 carbon atoms; in yet another embodiment, the alkoxy group contains 1 to 3 carbon atoms. The alkoxy group may be optionally substituted with one or more substituents described herein.
Examples of alkoxy groups include, but are not limited to, methoxy (MeO, -OCH)3) Ethoxy (EtO, -OCH)2CH3) 1-propoxy (n-PrO, n-propoxy, -OCH)2CH2CH3) 2-propoxy (i-PrO, i-propoxy, -OCH (CH)3)2) 1-butoxy (n-BuO, n-butoxy, -OCH)2CH2CH2CH3) 2-methyl-l-propoxy (i-BuO, i-butoxy, -OCH)2CH(CH3)2) 2-butoxy (s-BuO, s-butoxy, -OCH (CH)3)CH2CH3) 2-methyl-2-propoxy (t-BuO, t-butoxy, -OC (CH)3)3) And so on.
In the present application, "haloalkyl" or "haloalkoxy" means an alkyl or alkoxy group substituted with one or more halogen atoms, wherein the alkyl and alkoxy groups have the meaning as described herein, examples of which include, but are not limited to, trifluoromethyl, trifluoromethoxy, and the like.
In bookIn this application, aryl refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl group and a fused ring aryl group connected by carbon-carbon bond conjugation, two or more fused ring aryl groups connected by carbon-carbon bond conjugation. That is, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as an aryl group in the present application. Wherein the aryl group does not contain a hetero atom such as B, N, O, S, P or Si. For example, biphenyl, terphenyl, and the like are aryl groups in this application. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl, phenanthrenyl, pyrenyl,
Figure BDA0002626325870000042
and the like.
In the present application, a substituted aryl group may be one in which one or two or more hydrogen atoms in the aryl group are substituted with a group such as a deuterium atom, a halogen group, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio, haloalkyl, aryloxy, arylthio, silyl, alkylamino, aryl, heterocyclyl, and the like. Specific examples of heteroaryl-substituted aryl groups include, but are not limited to, dibenzofuranyl-substituted phenyl, dibenzothiophene-substituted phenyl, pyridine-substituted phenyl, and the like. It is understood that the number of carbon atoms in a substituted aryl group refers to the total number of carbon atoms in the aryl group and the substituents on the aryl group, for example, a substituted aryl group having a carbon number of 18, refers to a total number of carbon atoms in the aryl group and its substituents of 18.
In the present application, the fluorenyl group as the aryl group may be substituted, and two substituents may be combined with each other to form a spiro structure, and specific examples include, but are not limited to, the following structures:
Figure BDA0002626325870000041
in the present application, heteroaryl refers to a monovalent aromatic ring or derivative thereof that contains at least one heteroatom, which may be at least one of B, O, N, P, Si and S, in the ring. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. The term "heteroaryl" as used herein may include 1,2, 3,4, 5, 6, 7, 8, 9 or 10 heteroatoms selected from any of B, O, N, P, Si, Se and S, and may have 3 to 40 carbon atoms, in some embodiments 3 to 30 carbon atoms, and in other embodiments 3 to 20, or 3 to 18, or 3 to 12, or 12 to 18 carbon atoms. For example, the number of carbon atoms of the heteroaryl group can be 3,4, 5, 6, 7, 8, 9,10, 11, 12, 18, 20 or 40, and of course, other numbers are also possible, which are not listed here.
Exemplary heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-arylcarbazolyl (e.g., N-phenylcarbazolyl), N-heteroarylcarbazolyl (e.g., N-pyridylcarbazolyl), N-alkylcarbazolyl (e.g., N-methylcarbazolyl), and the like, without limitation. Wherein, thienyl, furyl, phenanthroline group and the like are heteroaryl of a single aromatic ring system type, and N-aryl carbazolyl and N-heteroaryl carbazolyl are heteroaryl of a polycyclic system type connected by carbon-carbon bond conjugation.
In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, alkoxy, alkylthio, haloalkyl, aryloxy, arylthio, silyl, alkylamino, aryl, heterocyclyl and the like. Specific examples of aryl-substituted heteroaryl groups include, but are not limited to, phenyl-substituted dibenzofuranyl, phenyl-substituted dibenzothiophenyl, phenyl-substituted pyridyl, and the like. It is understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituent on the heteroaryl group.
As used herein, the terms "silyl group" and "alkylsilyl group" mean the same and mean
Figure BDA0002626325870000051
Wherein R isG1、RG2、RG3Each independently an alkyl group, specific examples of alkylsilyl groups include, but are not limited to, trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, propyldimethylsilyl.
In the present application, arylsilyl means
Figure BDA0002626325870000052
Wherein R isG4、RG5、RG6Specific examples of the arylsilyl group, which are each independently an aryl group, include, but are not limited to, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, etc., but are not limited thereto.
In the present application, the heteroaryl group having 3 to n ring-forming carbon atoms means that the number of carbon atoms located on the heteroaryl ring in the heteroaryl group is 3 to n, and the number of carbon atoms in the substituent on the heteroaryl group is not counted.
In this application, the explanation for aryl applies to arylene, the explanation for heteroaryl applies equally to heteroarylene, the explanation for alkyl applies to alkylene, and the explanation for cycloalkyl applies to cycloalkylene.
In the present invention, the ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6-membered aryl. The 6-to 10-membered aromatic ring means a benzene ring, an indene ring, a naphthalene ring and the like.
The "ring" in the present application includes saturated rings, unsaturated rings; saturated rings, i.e., cycloalkyl, heterocycloalkyl, unsaturated rings, i.e., cycloalkenyl, heterocycloalkenyl, aryl, and heteroaryl.
An delocalized bond in the present application refers to a single bond extending from a ring system
Figure BDA0002626325870000053
It means that one end of the linkage may be attached to any position in the ring system through which the linkage extends, and the other end to the rest of the compound molecule. For example, as shown in the following formula (X), naphthyl represented by the formula (X) is connected to other positions of the molecule through two non-positioned connecting bonds penetrating through a double ring, and the meaning of the naphthyl represented by the formula (X-1) to the formula (X-10) includes any possible connecting mode shown in the formula (X-1).
Figure BDA0002626325870000054
Figure BDA0002626325870000061
For example, as shown in the following formula (X '), the phenanthryl group represented by the formula (X') is bonded to the rest of the molecule via an delocalized bond extending from the middle of the benzene ring on one side, and the meaning of the phenanthryl group includes any of the possible bonding modes as shown in the formulas (X '-1) to (X' -4).
Figure BDA0002626325870000062
An delocalized substituent, as used herein, refers to a substituent attached by a single bond extending from the center of the ring system, meaning that the substituent may be attached at any possible position in the ring system. For example, in the following formula (Y), the substituent R group represented by the formula (Y) is bonded to the quinoline ring via an delocalized bond, and the meaning thereof includes any of the possible bonding modes shown by the formulas (Y-1) to (Y-7).
Figure BDA0002626325870000063
The application provides a nitrogen-containing compound, wherein the structural formula of the nitrogen-containing compound is shown in chemical formula 1:
Figure BDA0002626325870000064
wherein the ring A is a fused aromatic ring with ring-forming carbon atoms of 10-14 or a fused heteroaromatic ring with ring-forming carbon atoms of 8-12, and the ring A is not a carbazole ring;
the ring B is a benzene ring, a fused aromatic ring with ring-forming carbon atoms of 10-14 or a fused heteroaromatic ring with ring-forming carbon atoms of 8-12;
the ring C is a benzene ring or a condensed aromatic ring with 10-14 ring-forming carbon atoms;
R1、R2、R3、R4the aryl group is the same or different and is independently selected from deuterium, a halogen group, a cyano group, a halogenated alkyl group with 1-12 carbon atoms, an alkenyl group with 2-10 carbon atoms, an alkynyl group with 2-10 carbon atoms, a cycloalkyl group with 3-12 carbon atoms, a heterocycloalkyl group with 2-10 carbon atoms, an alkoxy group with 1-12 carbon atoms, an alkylthio group with 1-12 carbon atoms, a trialkylsilyl group with 3-12 carbon atoms, an aryl group with 6-20 carbon atoms, a heteroaryl group with 3-20 carbon atoms, an aryloxy group with 6-20 carbon atoms, an arylthio group with 6-20 carbon atoms and an arylsilyl group with 6-18 carbon atoms;
n1represents a substituent R1Number of (2), n2Represents a substituent R2Number of (2), n3Represents a substituent R3Number of (2), n4Represents a substituent R4Number of (2), n1、n2、n3、n4Are the same or different from each other and are each independently selected from 0, 1,2, 3 or 4;
when n is1When greater than 1, any two of R1Same or different when n2When greater than 1, any two of R2The same or different; when n is3When greater than 1, any two of R3The same or different; when n is4When greater than 1, any two of R4The same or different;
w is selected from substituted or unsubstituted aryl with 6-40 carbon atoms and substituted or unsubstituted heteroaryl with 3-40 carbon atoms;
the substituents in W, which may be the same or different from each other, are each independently selected from the group consisting of: deuterium, a halogen group, a cyano group, an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, a heteroaralkyl group having 4 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms optionally substituted with 0, 1,2 or 3 substituents selected from deuterium, fluorine, chlorine, bromine, cyano and alkyl, a heteroaryl group having 3 to 30 carbon atoms optionally substituted with 0, 1,2 or 3 substituents selected from deuterium, fluorine, chlorine, bromine, cyano and alkyl, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, aryloxy group having 6 to 20 carbon atoms, arylthio group having 6 to 20 carbon atoms;
in the W, when two substituents are present on the same atom, optionally, the two substituents attached to the same atom are linked to each other to form a saturated or unsaturated 5-to 18-membered aliphatic ring or a 5-to 18-membered aromatic ring with the atom to which they are commonly attached.
In this application, ring A refers to
Figure BDA0002626325870000071
Ring B means
Figure BDA0002626325870000072
Wherein ring a is independently a fused aromatic ring, a fused heteroaromatic ring; ring B is independently a benzene ring, a fused aromatic ring, a fused heteroaromatic ring, for example, a naphthalene ring, an anthracene ring, a phenanthrene ring, a quinoline ring, an isoquinoline ring, or the like. Wherein the content of the first and second substances,
Figure BDA0002626325870000073
represents a chemical bond. For example, in the compounds
Figure BDA0002626325870000074
In the formula, ring A is naphthalene ring, and substituent R on ring A1The number is 0; ring B is naphthalene ring, substituent R on ring B2The number is 0. It is understood that ring B includes at least one benzene ring structure, which makes the nitrogen-containing compound of the present application include at least one carbazole structure.
Among the compounds of the present application, adamantane spiro-fused fluorenyl group, which is a part of the core of a nitrogen-containing compound, has high rigidity and a first triplet level, and a carbazole ring conjugated to the fused fluorenyl group in the compound has good hole transport ability, so that the nitrogen-containing compound of the present application is suitable as a host material of a light-emitting layer in an organic electroluminescent device. The adamantyl and the fluorenyl are screwed together, so that the electron cloud density of a large plane conjugated structure can be greatly increased through a hyperconjugation effect, the hole mobility of the nitrogen-containing compound is enhanced, the transmission balance of holes and electrons in a light-emitting layer is promoted, and the efficiency performance of an organic electroluminescent device is improved. Moreover, the improvement of the hole transport performance of the nitrogen-containing compound can improve the recombination rate of electrons and holes in the organic light-emitting layer, reduce or avoid the electrons from passing through the organic light-emitting layer and being transported to the hole transport layer, further effectively protect the hole transport layer material from the impact of the electrons, and prolong the service life of the organic electroluminescent device. Moreover, the adamantyl group screwed on the fluorenyl group has large space volume and strong rigidity, so that the mutual acting force between large plane conjugated structures can be reduced, the pi-pi stacking between molecules can be reduced, the stacking degree between molecules can be adjusted, the nitrogen-containing compound can have a more stable amorphous state during film forming, the film forming property of the nitrogen-containing compound can be improved, and the service life of an organic electroluminescent device can be further prolonged.
In an alternative embodiment of the present application, ring a in formula (1) is a naphthalene ring, an anthracene ring, a phenanthrene ring, a dibenzofuran ring, a dibenzothiophene ring, a thianthrene ring, a phenoxathiin ring, a dibenzodioxin ring, 10H-phenothiazine or 10H-phenoxazine; the ring B is a benzene ring, a naphthalene ring, a quinoline ring or an isoquinoline ring; the ring C is selected from a benzene ring, a naphthalene ring, an anthracene ring or a phenanthrene ring.
Because the ring A in the nitrogen-containing compound is a condensed aromatic ring structure, the large plane conjugated structure of the nitrogen-containing compound is larger, the rigidity is stronger, and the electron cloud density is higher, so that the hole transport capability of the nitrogen-containing compound is stronger, the recombination rate of electrons and holes in the organic light-emitting layer can be improved, the electron transmission to the hole transport layer through the organic light-emitting layer can be reduced or avoided, the hole transport layer material can be effectively protected from the impact of electrons, and the service life luminescence of the organic electroluminescent device can be improved.
In an alternative embodiment of the present application, in said formula (1)
Figure BDA0002626325870000081
Selected from the following structures:
Figure BDA0002626325870000082
in an alternative embodiment of the present application, in said formula (1)
Figure BDA0002626325870000083
Selected from the following structures:
Figure BDA0002626325870000084
in this application, R1、R2、R3、R4And the number of carbon atoms of W, indicatedIs the number of all carbon atoms. For example, if W is selected from substituted aryl groups having 10 carbon atoms, then all of the carbon atoms of the aryl group and substituents thereon are 10. For example, when W is p-tert-butylphenyl, W is a substituted phenyl group having 10 carbon atoms, and the number of ring-forming carbon atoms of W is 6.
In the present application, when a specific definition is not otherwise provided, "hetero" means that at least 1 hetero atom of B, N, O, S, Se, Si, or P, etc. is included in one functional group and the remaining atoms are carbon and hydrogen. An unsubstituted alkyl group can be a "saturated alkyl group" without any double or triple bonds.
It is understood that the number of carbon atoms of the substituted aryl group refers to the total number of carbon atoms of the aryl group and the substituents on the aryl group. For example, a substituted aryl group having 18 carbon atoms means that the total number of carbon atoms of the aryl group and the substituent on the aryl group is 18. For example, 9, 9-dimethylfluorenyl is a substituted aryl group having 15 carbon atoms.
In some embodiments, the nitrogen-containing compounds of the present application have a structural formula as shown in any one of formulas (f-1) to (f-16):
Figure BDA0002626325870000085
Figure BDA0002626325870000091
in an alternative embodiment of the present application, in said formula (1)
Figure BDA0002626325870000092
Selected from the following structures:
Figure BDA0002626325870000093
Figure BDA0002626325870000101
in some embodiments, the nitrogen-containing compound has a structural formula as shown in any one of formulas (f-17) to (f-32):
Figure BDA0002626325870000102
Figure BDA0002626325870000111
in some embodiments of the present application, W is
Figure BDA0002626325870000112
Wherein, L is independently selected from single bond, substituted or unsubstituted heteroarylene with 3-30 carbon atoms, and substituted or unsubstituted arylene with 6-30 carbon atoms; ar is selected from substituted or unsubstituted heteroaryl with 3-30 carbon atoms and substituted or unsubstituted aryl with 6-30 carbon atoms;
the substituent groups on the L and the Ar are one or more, and the substituent groups in the Ar and the L are the same or different and are respectively and independently selected from deuterium, a halogen group, a cyano group, an aryl group with 6-20 carbon atoms, a substituted or unsubstituted heteroaryl group with 3-20 carbon atoms, a halogenated alkyl group with 1-12 carbon atoms, an alkyl group with 1-12 carbon atoms, a cycloalkyl group with 3-12 carbon atoms, an alkoxy group with 1-12 carbon atoms, an alkylthio group with 1-12 carbon atoms, a trialkylsilyl group with 3-12 carbon atoms, an aryloxy group with 6-20 carbon atoms, an arylthio group with 6-20 carbon atoms and an arylsilyl group with 6-18 carbon atoms;
when two substituents are present on the same atom, optionally, the two substituents attached to the same atom can be linked to each other to form a saturated or unsaturated 5-to 13-membered aliphatic ring or a 5-to 13-membered aromatic ring with the atoms to which they are commonly attached. More specifically, the substitution in the substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms is selected from: fluoro, deuterium, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyridyl.
Wherein, when a plurality of substituents are provided on L, the substituents on L may be the same or different, and wherein, when a plurality of substituents are provided on Ar, the substituents on Ar may be the same or different.
In the present application, the substituent "plurality" means more than 1, and may be 2, 3,4, 5, 6, 7 or 8.
In some embodiments of the present application, L is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, and a substituted or unsubstituted heteroarylene group having 5 to 14 carbon atoms. The substituents in L are each independently selected from: deuterium, fluorine, chlorine, bromine, cyano, an alkyl group having 1 to 4 carbon atoms, a halogenated alkyl group having 1 to 4 carbon atoms, a trialkylsilyl group having 3 to 9 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an aryl group having 6 to 15 carbon atoms and a heteroaryl group having 3 to 12 carbon atoms, and when two substituents are present on the same atom, optionally, the two substituents attached to the same atom can be connected to each other so that the atom to which they are commonly attached forms a saturated or unsaturated 5 to 13-membered aliphatic ring or a 5 to 13-membered aromatic ring.
In some embodiments of the present application, the L is selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted 9, 9-dimethylfluorenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted 9, 9-dimethyl-9H-9-silafluorenylene group, a substituted or unsubstituted dibenzofuranene group, a substituted or unsubstituted dibenzothiophenylene group, a substituted or unsubstituted quinolylene group, a substituted or unsubstituted isoquinolylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted phenanthrylene group, a substituted or unsubstituted anthrylene group, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted spirobifluorenylene group, a spiro [ cyclopentane-1 ], one of 9 '-fluorene subunit and spiro [ cyclohexane-1, 9' -fluorene ] subunit, or subunit group formed by connecting two or three of the above subunits through single bond; the substituents in L are the same or different from each other and are each independently selected from the group consisting of deuterium, fluoro, chloro, cyano, methyl, ethyl, isopropyl, n-propyl, tert-butyl, methoxy, ethoxy, trifluoromethyl, trimethylsilyl, phenyl, cyano-substituted phenyl, fluoro-substituted phenyl, naphthyl, quinoline, isoquinolinyl, pyridyl, cyclopentyl, and cyclohexyl.
Alternatively, L is selected from a single bond, or from the group consisting of groups represented by formula j-1 through formula j-13:
Figure BDA0002626325870000121
wherein M is2Selected from a single bond or
Figure BDA0002626325870000122
Q1～Q5Each independently selected from N or C (J)5) And Q is1～Q5At least one is selected from N; when Q is1～Q5Two or more of them are selected from C (J)5) When, two arbitrary J5The same or different;
Q6～Q13each independently selected from N or C (J)6) And Q is6～Q13At least one is selected from N; when Q is6～Q13Two or more of them are selected from C (J)6) When, two arbitrary J6The same or different;
Q14～Q23each independently selected from N, C or C (J)7) And Q is14～Q23At least one is selected from N; when Q is14～Q23Two or more of them are selected from C (J)7) When, two arbitrary J7The same or different;
Q24～Q33each independently selected from N, C or C (J)8)，And Q24～Q33At least one is selected from N; when Q is24～Q33Two or more of them are selected from C (J)8) When, two arbitrary J8The same or different;
E1～E14、J5～J8each independently selected from: hydrogen, deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 9 carbon atoms, an arylsilyl group having 8 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, a heterocycloalkenyl group having 4 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkylthio group having 1 to 10 carbon atoms, an aryloxy group having 6 to 18 carbon atoms, and an arylthio group having 6 to 18 carbon atoms;
e1～e14with erIs represented by1～E14With ErR is a variable and is an arbitrary integer of 1 to 14, erRepresents a substituent ErThe number of (2); when r is selected from 1,2, 3,4, 5, 6, 9, 13 or 14, erSelected from 1,2, 3 or 4; when r is selected from 7 or 11, erSelected from 1,2, 3,4, 5 or 6; when r is 12, erSelected from 1,2, 3,4, 5, 6 or 7; when r is selected from 8 or 10, erSelected from 1,2, 3,4, 5, 6, 7 or 8; when e isrWhen greater than 1, any two of ErThe same or different;
K3selected from O, S, Se, N (E)15)、C(E16E17)、Si(E18E19) (ii) a Wherein each E15、E16、E17、E18And E19Each independently selected from: hydrogen, aryl with 6-20 carbon atoms, heteroaryl with 3-20 carbon atoms, alkyl with 1-10 carbon atoms and cycloalkyl with 3-10 carbon atoms;
or, optionally, E above16And E17Are linked to form a 5-to 13-membered aliphatic ring with the atoms to which they are commonly attached orA 5 to 13 membered aromatic ring;
or, optionally, E above18And E19Are linked to each other to form a 5-to 13-membered aliphatic ring or a 5-to 13-membered aromatic ring with the atoms to which they are commonly linked;
each K4Independently selected from single bond, O, S, Se, N (E)20)、C(E21E22)、Si(E23E24) (ii) a Wherein each E20、E21、E22、E23、E24Each independently selected from: hydrogen, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, and heterocycloalkyl having 2 to 10 carbon atoms;
or, optionally, E above21And E22Are linked to each other to form a 5-to 13-membered aliphatic ring or a 5-to 13-membered aromatic ring with the atoms to which they are commonly linked;
or, optionally, E above23And E24Are linked to each other to form a 5-to 13-membered aliphatic ring or a 5-to 13-membered aromatic ring with the atoms to which they are commonly linked.
For example, L is
Figure BDA0002626325870000131
When M is present2And K4Is a single bond, E11Are each hydrogen, K3Is C (E)16E17) When, optionally, E is attached to the same atom16And E17The atoms which are linked to each other to form a 5-to 13-membered aliphatic ring, saturated or unsaturated, with which they are linked together refer to E16And E17Can be linked to each other to form a 5-to 13-membered ring, or can be present independently of each other; when E is16And E17When an aliphatic ring is formed, the number of atoms of the ring may be 5-membered, for example
Figure BDA0002626325870000132
Or may be a 6-membered ring, e.g.
Figure BDA0002626325870000133
May also be a 10-membered ring, e.g.
Figure BDA0002626325870000134
Of course, E16And E17The number of atoms in the rings formed by the interconnections may also be other values, which are not listed here. At the same time, E16And E17The rings formed by the interconnection may also be aromatic, such as a 13-membered aromatic ring,
Figure BDA0002626325870000135
optionally, E18And E19To each other to form a 5-to 13-membered aliphatic or aromatic ring with the atoms to which they are commonly attached16And E17The same is true. Optionally, E21And E22To each other to form a 5-to 13-membered aliphatic ring or a 5-to 13-membered aromatic ring with the atoms to which they are commonly attached16And E17The same is true. Optionally, E23And E24To each other to form a 5-to 13-membered aliphatic ring or a 5-to 13-membered aromatic ring with the atoms to which they are commonly attached16And E17The same is true.
Alternatively, Q1～Q5Only one of which is selected from N.
Alternatively, Q6～Q13Only one of which is selected from N.
Alternatively, Q14～Q23Only one of which is selected from N.
Alternatively, Q24～Q33Only one of which is selected from N.
In some embodiments of the present application, L is selected from the group consisting of a single bond, unsubstituted L1Substituted L1Wherein, L is unsubstituted1Selected from the group consisting of:
Figure BDA0002626325870000141
wherein, substituted L1Is unsubstituted L1By one or more members selected from deuteriumFluorine, chlorine, bromine, cyano, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, trialkylsilyl having 3 to 9 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 15 carbon atoms and heteroaryl having 3 to 12 carbon atoms, and when substituted L is a group1When the number of the substituent(s) is plural, any two of the substituents may be the same or different. Further, the above-mentioned substituted L1Is unsubstituted L1A group substituted with 0, 1,2, 3 or 4 substituents selected from deuterium, fluorine, chlorine, bromine, cyano, methyl, ethyl, propyl, tert-butyl, phenyl, biphenyl, naphthyl, pyridyl, carbazolyl, dibenzothienyl, dibenzofuranyl, and when substituted, L1When the number of the substituent(s) is plural, any two of the substituents may be the same or different.
In yet other more specific embodiments herein, the L is a single bond or any one of the following groups:
Figure BDA0002626325870000142
Figure BDA0002626325870000151
in yet other more specific embodiments herein, the L is a single bond or any one of the following groups:
Figure BDA0002626325870000152
in some embodiments of the present application, Ar is selected from the group consisting of groups represented by formulas i-1 through i-18:
Figure BDA0002626325870000153
Figure BDA0002626325870000161
wherein M is1Selected from a single bond or
Figure BDA0002626325870000162
G1～G5Each independently selected from N or C (F)1) And G is1～G5At least one is selected from N; when G is1～G5Two or more of C (F)1) When, two arbitrary F1The same or different;
G6～G13each independently selected from N or C (F)2) And G is6～G13At least one is selected from N; when G is6～G13Two or more of C (F)2) When, two arbitrary F2The same or different;
G14～G23each independently selected from N or C (F)3) And G is14～G23At least one is selected from N; when G is14～G23Two or more of C (F)3) When, two arbitrary F3Identical or different or, optionally, two adjacent F3Mutually connected to form a 5-to 10-membered aromatic ring or a 5-to 10-membered heteroaromatic ring;
G24～G33each independently selected from N or C (F)4) And G is24～G33At least one is selected from N; when G is24～G33Two or more of C (F)4) When, two arbitrary F4The same or different; or, optionally, two adjacent F4Mutually connected to form a 5-to 10-membered aromatic ring or a 5-to 10-membered heteroaromatic ring;
G34～G37each independently selected from N or C (F)5) When G is34～G37Two or more of C (F)5) When, two arbitrary F5The same or different; or, optionally, two adjacent F5Mutually connected to form a 5-to 10-membered aromatic ring or a 5-to 10-membered heteroaromatic ring;
G38～G45each independently selected from N or C (F)6) And G is38～G45At least one is selected from N; when G is38～G45Two or more of C (F)6) When, two arbitrary F6The same or different;
G46～G53each independently selected from N or C (F)7) And G is46～G53At least one is selected from N; when G is46～G53Two or more of them are selected from C (F)7) When, two arbitrary F7The same or different; or, optionally, two adjacent F7Are connected with each other to form a 5-to 10-membered aromatic ring or a 5-to 10-membered heteroaromatic ring.
In the formula i-16, "optionally, two adjacent F5Are linked to each other to form a 5-to 10-membered aromatic ring or a 5-to 10-membered heteroaromatic ring "means any two adjacent ring atoms, G34And G35Or G35And G36Or G36And G37Are all C (F)5) When two adjacent F5May be present independently of each other or may be linked to each other to form, together with the ring atoms to which they are attached, a fused aromatic or heteroaromatic ring. For example, when i-16
Figure BDA0002626325870000163
In, K5Is sulfur, G34And G35Are all CH, G36And G37Are all C (F)5) And both form a 6-membered aromatic ring, i.e. formula i-16 is
Figure BDA0002626325870000171
Adjacent F5The ring formation can also be the formation of other aromatic or heteroaromatic rings, which are not further listed here. Optionally, two adjacent F3、F4Or F7The meaning of the rings connected with each other is the same, and they are not listed.
D1Selected from hydrogen, deuterium, fluorine, chlorine, bromineA cyano group, a trialkylsilyl group having 3 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and an alkylthio group having 1 to 10 carbon atoms;
D2～D9、D21each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, heteroaryl having 3 to 18 carbon atoms;
D10～D20、F1～F7each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms and a heteroaryl group having 3 to 18 carbon atoms, which are optionally substituted with 0, 1,2 or 3 substituents selected from deuterium, fluorine, chlorine, cyano, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylamino group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkylsilyl group having 3 to 9 carbon atoms;
d1～d21with dkIs represented by1～D21With DkK is a variable and represents an arbitrary integer of 1 to 21, dkRepresents a substituent DkThe number of (2); wherein, when k is selected from 5 or 17, dkSelected from 1,2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 21, dkSelected from 1,2, 3 or 4; when k is selected from 1,3, 4,6, 9 or 14, dkSelected from 1,2, 3,4 or 5; when k is 13, dkSelected from 1,2. 3,4, 5 or 6; when k is selected from 10 or 19, dkSelected from 1,2, 3,4, 5, 6 or 7; when k is 20, dkSelected from 1,2, 3,4, 5, 6, 7 or 8; when k is 11, dkSelected from 1,2, 3,4, 5, 6, 7, 8 or 9; and when d iskWhen greater than 1, any two DkThe same or different;
K1and K6Each independently selected from O, S, N (D)22)、C(D23D24)、Si(D28D29) (ii) a Wherein each D22、D23、D24、D28、D29Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms;
or, optionally, D above23And D24Are linked to each other to form a 5-to 14-membered aliphatic ring or a 5-to 14-membered aromatic ring with the atoms to which they are commonly linked;
or, optionally, D above28And D29Are linked to each other to form a 5-to 14-membered aliphatic ring or a 5-to 14-membered aromatic ring with the atoms to which they are commonly linked;
K2selected from the group consisting of single bond, O, S, N (D)25)、C(D26D27)、Si(D30D31) (ii) a Wherein each D25、D26、D27、D30、D31Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms,
or, optionally, D above26And D27Are linked to each other to form a 5-to 14-membered aliphatic ring or a 5-to 14-membered aromatic ring with the atoms to which they are commonly linked;
or, optionally, D above30And D31Are linked to each other to form a 5-to 14-membered aliphatic ring or a 5-to 14-membered aromatic ring with the atoms to which they are commonly linked;
K5selected from O, S, Se, N (D)32)、C(D33D34) Wherein D is32、D33And D34Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms.
"optionally, D above23And D24Interconnected to form a 5-to 14-membered aliphatic ring or a 5-to 14-membered aromatic ring with the atoms to which they are commonly attached "means that D23And D24Can be connected with each other to form a ring, and can also exist independently of each other. For example, in the formula i-19,
Figure BDA0002626325870000172
in (A) when M1Is a single bond, K2Is a single bond, D19Are each hydrogen, K1Is C (D)23D24) When D is present23And D24When forming a ring, the ring may be a 5-membered aliphatic ring, e.g.
Figure BDA0002626325870000181
Or may be a 6-membered alicyclic ring, e.g.
Figure BDA0002626325870000182
May be a 13-membered aromatic ring, for example
Figure BDA0002626325870000183
Figure BDA0002626325870000184
Figure BDA0002626325870000185
Of course, D23And D24The number of carbon atoms in the rings formed by the interconnections may also be other values, which are not listed here. Optionally, D26And D27D and D are linked to each other to form a 5-to 14-membered aliphatic or aromatic ring with the atoms to which they are commonly linked23And D24The same is true. Optionally, D28And D29，D26And D27，D30And D31D and the meanings of being linked to each other so as to form a 5-to 14-membered aliphatic or aromatic ring with the atoms to which they are jointly attached23And D24The same is true.
Alternatively, G1～G5At least two of which are selected from N.
Alternatively, G6～G13At least two of which are selected from N.
Alternatively, G14～G23At least two of which are selected from N.
Alternatively, G24～G33At least two of which are selected from N.
Alternatively, G38～G45At least two of which are selected from N.
Alternatively, G46～G53At least two of which are selected from N.
In some embodiments of the present application, Ar is selected from the group consisting of substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 25 carbon atoms; the substituents on Ar are one or more, the same or different from each other, and each independently selected from deuterium, fluorine, chlorine, a cyano group, an aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a trialkylsilyl group having 3 to 9 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an arylthio group having 6 to 20 carbon atoms, and an arylsilyl group having 6 to 18 carbon atoms. More specifically, the substitution in the substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms is selected from: fluoro, deuterium, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyridyl.
In some more specific embodiments herein, Ar is selected from unsubstituted Ar1Or substituted Ar1Wherein, Ar is unsubstituted1Selected from the group consisting ofGroup consisting of:
Figure BDA0002626325870000186
Figure BDA0002626325870000191
wherein Z is1And Z2Each independently selected from hydrogen, aryl having 6 to 20 carbon atoms, and heteroaryl having 3 to 20 carbon atoms; any two Z1Identical or different, any two Z2The same or different;
wherein, substituted Ar1Is unsubstituted Ar1A group substituted by one or more groups selected from deuterium, fluorine, chlorine, cyano, C1-4 alkyl, C1-4 alkoxy, C1-4 alkylamino, C3-7 cycloalkyl, C6-14 aryl, C3-12 heteroaryl, C1-4 alkylthio, C1-4 haloalkyl, C3-9 alkylsilyl, and when Ar is Ar1When the number of the substituent(s) is plural, any two of the substituents may be the same or different.
In addition, "substituted Ar1Is unsubstituted Ar1Substituted by one or more substituents which may be substituted for the unsubstituted Ar mentioned above1The hydrogen atom at any position in (1) may be, for example, a substituent group Z1Any hydrogen atom in (1). Further, substituted Ar1Is unsubstituted Ar1Substituted by one or more groups selected from deuterium, fluoro, chloro, cyano, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyridyl, trifluoromethyl, trimethylsilyl and the like, and when Ar is Ar1When the number of the substituent(s) is plural, any two of the substituents may be the same or different.
In still other specific embodiments, Ar is selected from unsubstituted Ar1Or substituted Ar1Wherein, Ar is unsubstituted1Is also selected from the group consisting of:
Figure BDA0002626325870000201
wherein, substituted Ar1Is unsubstituted Ar1A group substituted by one or more groups selected from deuterium, fluorine, chlorine, cyano, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, aryl having 6 to 14 carbon atoms, heteroaryl having 3 to 12 carbon atoms, alkylthio having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms and alkylsilyl having 3 to 9 carbon atoms, and when Ar is Ar1When the number of the substituent(s) is plural, any two of the substituents may be the same or different.
Further, Z1And Z2Each independently selected from: hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted perylene, substituted or unsubstituted fluoranthryl, substituted or unsubstituted anthryl
Figure BDA0002626325870000205
A phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted carbazol-9-ylphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoxazine group, a substituted or unsubstituted triphenylene group;
Z1and Z2Each of the substituents in (1) to (3)Independently selected from: fluorine, deuterium, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, trifluoromethyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl. When Z is in the above range1Or Z2When hydrogen is used, the delocalized linkage may be bonded to Ar instead of the hydrogen atom1The above. For example,
Figure BDA0002626325870000202
Included
Figure BDA0002626325870000203
in some embodiments herein, Ar may be selected from an aryl group or an electron rich heteroaryl group, where the heteroatom on the electron rich heteroaryl group is capable of increasing the electron cloud density of the conjugated system of the heteroaryl group as a whole rather than decreasing the electron cloud density of the conjugated system of the heteroaryl group, e.g., the lone pair of electrons on the heteroatom may participate in the conjugated system to increase the electron cloud density of the conjugated system of the heteroaryl group. For example, electron-rich heteroaryl groups can include, but are not limited to, carbazolyl, dibenzofuranyl, dibenzothiazolyl, furanyl, pyrrolyl, and the like. Since both the aryl group and the electron-rich heteroaryl group can effectively enhance the electron cloud density of the nitrogen-containing compound and can adjust the HOMO energy level of the nitrogen-containing compound, the nitrogen-containing compound will have better hole transport ability. Thus, the nitrogen-containing compound can be used as a hole type organic light-emitting layer main material and matched with an electron type organic light-emitting layer main material for transmitting electrons to jointly form the main material of the organic light-emitting layer.
In some embodiments of the present application, Ar is selected from the following structures:
Figure BDA0002626325870000204
Figure BDA0002626325870000211
Figure BDA0002626325870000221
in some embodiments of the present application, Ar is an electron-deficient heteroaryl group (also referred to as an electron-deficient heteroaryl group), on which a heteroatom is capable of reducing the electron cloud density of the conjugated system of the heteroaryl group as a whole rather than increasing the electron cloud density of the conjugated system of the heteroaryl group, e.g., the lone pair of electrons on the heteroatom do not participate in the conjugated system, and the heteroatom reduces the electron cloud density of the conjugated system due to the stronger electronegativity. By way of example, electron-deficient heteroaryl groups can include, but are not limited to, pyridyl, pyrimidinyl, s-triazinyl, quinolinyl, isoquinolinyl, benzopyrazolyl, benzimidazolyl, quinoxalinyl, phenanthroline, and the like. Thus, Ar can form an electron transport core group of the nitrogen-containing compound, so that the nitrogen-containing compound can effectively realize electron transport and can effectively balance the transport rates of electrons and holes in the organic light-emitting layer. Thus, the nitrogen-containing compound can be used as a bipolar organic light-emitting layer main material to simultaneously transport electrons and holes, and can also be used as an electron type organic light-emitting layer main material to be matched with a hole type organic light-emitting layer main material.
In some embodiments of the present application, Ar is selected from the following structures:
Figure BDA0002626325870000222
Figure BDA0002626325870000231
in some embodiments, R1、R2、R3、R4The same or different from each other, and are independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 4 carbon atoms, an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, and a carbon atom2-6 alkynyl groups, 5-10 cycloalkyl groups, 4-6 heterocycloalkyl groups, 1-4 alkoxy groups, 1-4 alkylthio groups, 3-9 trialkylsilyl groups, 6-15 aryl groups, 3-12 heteroaryl groups, 6-15 aryloxy groups, 6-15 arylthio groups, and triphenylsilyl groups.
In some more specific embodiments, R1、R2、R3、R4Identical or different from each other and are each independently selected from deuterium, fluorine, chlorine, bromine, cyano, methyl, isopropyl, ethylisopropyl, cyclopropyl, tert-butyl, ethoxy, trifluoromethyl, trimethylsilyl, phenyl, pyridyl, dimethylfluorenyl, dibenzofuranyl, dibenzothienyl, pyrimidinyl, triazinyl, triphenylsilyl, n1、n2、n3、n4Are the same or different from each other and are each independently selected from 0, 1,2, 3 or 4.
Optionally, the nitrogen-containing compound is selected from the group consisting of:
Figure BDA0002626325870000241
Figure BDA0002626325870000251
Figure BDA0002626325870000261
Figure BDA0002626325870000271
Figure BDA0002626325870000281
Figure BDA0002626325870000291
the application also provides an organic electroluminescent device, which comprises an anode and a cathode which are oppositely arranged, and a functional layer arranged between the anode and the cathode, wherein the functional layer comprises a hole injection layer, a hole transport layer, an organic luminescent layer, an electron transport layer and an electron injection layer; the organic light emitting layer contains the above-described nitrogen-containing compound to improve voltage characteristics, efficiency characteristics, and lifetime characteristics of the organic electroluminescent device.
For example, as shown in fig. 1, the organic electroluminescent device may include an anode 100, a hole transport layer 321, an organic light emitting layer 330, an electron transport layer 340, and a cathode 200, which are sequentially stacked. The nitrogen-containing compound provided by the application can be applied to the organic light-emitting layer 330 of the organic electroluminescent device to prolong the service life of the organic electroluminescent device, improve the light-emitting efficiency of the organic electroluminescent device or reduce the driving voltage of the organic electroluminescent device.
Optionally, the anode 100 comprises an anode material, which is optionally a material with a large work function that facilitates hole injection into the functional layer. Specific examples of anode materials include, but are not limited to: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metals and oxides, e.g. ZnO: Al or SnO2Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole and polyaniline. Optionally including a transparent electrode comprising Indium Tin Oxide (ITO) as the anode.
Alternatively, the hole transport layer 321 may include one or more hole transport materials, and the hole transport material may be selected from carbazole multimer, carbazole-linked triarylamine-based compound, or other types of compounds, which are not specifically limited herein.
Alternatively, the organic light emitting layer 330 may include a host material and a guest material, and holes injected into the organic light emitting layer 330 and electrons injected into the organic light emitting layer 330 may be recombined in the organic light emitting layer 330 to form excitons, which transfer energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
In one embodiment herein, the host material may be comprised of the nitrogen-containing compounds herein, and in particular, nitrogen-containing compounds that include electron deficient aromatic heterocycles in the W group. The nitrogen-containing compound can simultaneously transmit electrons and holes and balance the transmission efficiency of the holes and the electrons, so that the electrons and the holes can be efficiently compounded in the organic light-emitting layer, and the light-emitting efficiency of the organic electroluminescent device is improved.
In another embodiment of the present application, the host material may be a composite material, for example, may include the nitrogen-containing compound of the present application and an electron-type organic light emitting layer host material. The nitrogen-containing compound can effectively transmit holes, so that the hole transmission efficiency is balanced with the electron transmission efficiency of the organic light-emitting layer, electrons and holes can be efficiently compounded in the organic light-emitting layer, and the luminous efficiency of an organic electroluminescent device is improved. By way of example, the host material may include a nitrogen-containing compound of the present application and GH-n 1.
The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which is not particularly limited in the present application. In one embodiment of the present application, the guest material of the organic light emitting layer 330 may be Ir (piq)2(acac) and the like. In another embodiment of the present application, the guest material of the organic light emitting layer 330 may be Ir (ppy)3And the like.
Alternatively, the electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from, but not limited to, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials.
Alternatively, the cathode 200 may comprise a cathode material, which is a material with a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multilayer material such as LiF/Al, Liq/Al, LiO2Al, LiF/Ca, LiF/Al and BaF2and/Ca. A metal electrode comprising aluminum may optionally be included as a cathode. In one embodiment of the present application, the material of the cathode 200 may be a magnesium silver alloy.
Optionally, as shown in fig. 1, a hole injection layer 310 may be further disposed between the anode 100 and the hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not limited in this application. For example, the hole injection layer 310 may be composed of F4-TCNQ.
Alternatively, as shown in fig. 1, an electron blocking layer 322 may be further disposed between the hole transport layer 321 and the organic light emitting layer 330 to block electrons from being transported to the hole transport layer 321 side, to improve a recombination rate of the electrons and the holes in the organic light emitting layer 330, and to protect the hole transport layer 321 from the impact of the electrons. The material of the electron blocking layer 322 may be carbazole multimer, carbazole-linked triarylamine-based compound, or other feasible structures.
Optionally, as shown in fig. 1, an electron injection layer 350 may be further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material. For example, the electron injection layer 350 may include LiQ.
The present application also provides an electronic device 400, as shown in fig. 2, where the electronic device 400 includes any one of the organic electroluminescent devices described in the above organic electroluminescent device embodiments. The electronic device 400 may be a display device, a lighting device, an optical communication device, or other types of electronic devices, and may include, but is not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like. Since the electronic device 400 has any one of the organic electroluminescent devices described in the above embodiments of the organic electroluminescent device, the same advantages are obtained, and details are not repeated herein.
Synthesis example:
in the synthesis examples described below, all temperatures are in degrees celsius unless otherwise stated. Some of the reagents were purchased from commercial suppliers such as Aldrich Chemical Company, Arco Chemical Company and Alfa Chemical Company and were used without further purification unless otherwise stated. The other conventional reagents were purchased from Shantou Wen Long chemical reagent factory, Guangdong Guanghua chemical reagent factory, Guangzhou chemical reagent factory, Tianjin Haojian Yunyu chemical Co., Ltd, Tianjin Shucheng chemical reagent factory, Wuhan Xin Huayuan science and technology development Co., Ltd, Qingdao Tenglong chemical reagent Co., Ltd, and Qingdao Kaolingyi factory. The anhydrous solvent such as anhydrous tetrahydrofuran, dioxane, toluene, diethyl ether and the like is obtained by refluxing and drying the metal sodium. The anhydrous dichloromethane and chloroform are obtained by calcium hydride reflux drying. Ethyl acetate, petroleum ether, N-hexane, N-dimethylacetamide and N, N-dimethylformamide were used after previously drying over anhydrous sodium sulfate.
The reactions in the various synthesis examples were generally carried out under a positive pressure of nitrogen or argon, or by placing a drying tube over an anhydrous solvent (unless otherwise stated); in the reaction, the reaction flask was closed with a suitable rubber stopper, and the substrate was injected into the reaction flask via a syringe. The individual glassware used was dried.
During purification, the chromatographic column is a silica gel column, and silica gel (300-400 mesh) is purchased from Qingdao oceanic plants.
In each synthesis example, the conditions for measuring low resolution Mass Spectrometry (MS) data were: agilent 6120 four-stage rod HPLC-M (column model: Zorbax SB-C18, 2.1X 30mm,3.5 μ M, 6min, flow rate 0.6 mL/min. mobile phase: ratio of 5% -95% (acetonitrile containing 0.1% formic acid) in (water containing 0.1% formic acid)), using electrospray ionization (ESI), at 210nm/254nm, with UV detection.
Hydrogen nuclear magnetic resonance spectroscopy: bruker 400MHz NMR instrument in CD at room temperature2Cl2TMS (0ppm) was used as a reference standard for the solvent (in ppm). When multiple peaks occur, the following abbreviations will be used: s (singleton), d (doublet), t (triplet), m (multiplet).
The target compounds were detected by UV at 210nm/254nm using Agilent 1260pre-HPLC or Calesep pump 250pre-HPLC (column model: NOVASEP 50/80mm DAC).
The synthesis of the compounds of the present application was performed using the following method:
Figure BDA0002626325870000311
1-bromo-2-iodonaphthalene (40 g; 120.12mmol), 3-chlorobenzeneboronic acid (20.7 g; 132.13mmol), tetrakis (triphenylphosphine) palladium (2.8 g; 2.4mmol), potassium carbonate (41.5 g; 300.3mmol), tetrabutylammonium bromide (7.7 g; 24.0mmol) were added to the flask, and a mixed solvent of toluene (320mL), ethanol (80mL) and water (80mL) was added, and the temperature was raised to 80 ℃ under nitrogen protection℃Keeping the temperature and stirring for 8 hours; cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by column chromatography on silica gel using n-heptane as the mobile phase gave the product intermediate a-1 as a pale grey solid (26.7 g; yield 70%).
Using a similar method to the synthesis of intermediate a-1, intermediate B-1 to intermediate k-1 were synthesized using the compound shown in reactant a in table 1 instead of 1-bromo-2 iodonaphthalene and the compound shown in reactant B instead of 3-chlorobenzeneboronic acid:
table 1: synthesis of intermediate b-1 to intermediate k-1
Figure BDA0002626325870000312
Figure BDA0002626325870000321
Figure BDA0002626325870000322
Adding intermediate a-1(26.7g, 84.1mmol) and tetrahydrofuran (220mL) into a flask, cooling to-78 ℃ under the protection of nitrogen, adding n-butyllithium tetrahydrofuran (2.5M) solution (50mL, 126.1mmol) dropwise under stirring, stirring while maintaining the temperature constant for 1 hour after dropwise addition, adding adamantanone (10.1g, 67.2mmol) dissolved in tetrahydrofuran (50mL) dropwise at-78 ℃, keeping the temperature constant for 1 hour after dropwise addition, raising the temperature to room temperature, stirring for 24 hours, adding hydrochloric acid (12M) (15mL, 189.1mmol) in water (60mL) to the reaction solution, stirring for 1 hour, separating, washing the organic phase to neutrality with water, adding anhydrous magnesium sulfate, drying under reduced pressure to remove the solvent to obtain a crude product, purifying the crude product by silica gel column chromatography using an ethyl acetate/n-heptane system to obtain white solid intermediate a-2(16.3g, yield 50%).
Using a similar procedure to the synthesis of intermediate a-2, intermediate b-2 to intermediate k-2 were synthesized using reactant C shown in table 2 instead of intermediate a-1:
table 2: synthesis of intermediate b-2 to intermediate k-2
Figure BDA0002626325870000331
Figure BDA0002626325870000341
Figure BDA0002626325870000342
Adding the intermediate a-2(16.3g, 41.9mmol) and glacial acetic acid (165mL) into a flask, slowly dropwise adding a concentrated sulfuric acid (98%) (0.8mL, 8.4mmol) solution in acetic acid (20mL) under the condition of nitrogen protection and normal temperature stirring, raising the temperature to 80 ℃ after dropwise addition, and stirring for 2 hours; cooling to room temperature, filtering the precipitated solid, leaching the filter cake with water and ethanol, and drying to obtain a crude product; the crude product was purified by column chromatography on silica gel using a dichloromethane/n-heptane system to give intermediate a-3(10.9g, yield 70%) as a white solid.
Intermediates b-3 to k-3 were synthesized using a similar procedure as described above, substituting intermediate a-2 with reactant D in table 3 below:
table 3: synthesis of intermediate b-3 to intermediate k-3
Figure BDA0002626325870000343
Figure BDA0002626325870000351
Figure BDA0002626325870000352
Adding the intermediate a-3(10.9g, 29.4mmol), pinacol diboron diborate (9.0g, 35.3mmol), tris (dibenzylideneacetone) dipalladium (0.27g, 0.29mmol), 2-dicyclohexylphosphonium-2 ',4',6' -triisopropylbiphenyl (0.27g, 0.58mmol), potassium acetate (8.65g, 88.1mmol) and 1, 4-dioxane (80mL) to a flask, and stirring at 100 ℃ under nitrogen protection for 16 hours under reflux; cooling to room temperature, adding dichloromethane and water into the reaction solution, separating, washing the organic phase with water, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; the crude product was purified by column chromatography on silica gel using a dichloromethane/n-heptane system to give intermediate a-4(7.5g, yield 55%) as a white solid.
Intermediates b-4 to i-4 were synthesized using a similar procedure as described above, substituting intermediate a-3 with reactant E in table 4 below:
table 4: synthesis of intermediate b-4 to intermediate i-4
Figure BDA0002626325870000361
Figure BDA0002626325870000371
Adding the intermediate k-3(7g,20.8mmol) and N-bromosuccinimide (7.4g,41.6mmol) into a flask, adding DMF (N, N-dimethylformamide) (70mL) as a solvent, heating to 80 ℃ under the protection of nitrogen, keeping the temperature and stirring for 16 hours; cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by silica gel column chromatography using a dichloromethane/n-heptane mixed solvent as a mobile phase gave the product intermediate k-4 as a white solid (6.47g, yield 75%).
Intermediate j-4 was synthesized using a similar procedure as described above, substituting intermediate k-3 with reactant F in table 5 below:
table 5: synthesis of intermediate j-4
Figure BDA0002626325870000372
Figure BDA0002626325870000373
Intermediate k-4(6.4g, 15.4mmol), pinacol diboron diborate (4.3g, 16.9mmol), [1,1' -bis (diphenylphosphino) ferrocene ] dichloropalladium (0.23g, 0.31mmol), potassium acetate (3.02g, 30.8mmol) and 1, 4-dioxane (65mL) were added to the flask and stirred at 100 ℃ under nitrogen protection at reflux for 6 hours; cooling to room temperature, adding dichloromethane and water into the reaction solution, separating, washing the organic phase with water, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; the crude product was purified by column chromatography on silica gel using a dichloromethane/n-heptane system to give intermediate k-5(4.8g, yield 68%) as a white solid.
Intermediate j-5 was synthesized using a similar procedure as described above, substituting intermediate k-3 with reactant F in table 6 below:
table 6: synthesis of intermediate j-5
Figure BDA0002626325870000374
Figure BDA0002626325870000381
Adding the intermediate a-4(7.5 g; 16.2mmol), 3-bromocarbazole (4.2 g; 17.0mmol), tetrakis (triphenylphosphine) palladium (0.4 g; 0.3mmol), potassium carbonate (5.6 g; 40.5mmol), tetrabutylammonium bromide (1.0 g; 3.2mmol) into a flask, adding a mixed solvent of toluene (80mL), ethanol (20mL) and water (20mL), heating to 80 ℃ under the protection of nitrogen, keeping the temperature and stirring for 12 hours; cooling to room temperature, stopping stirring, washing the reaction solution with water, separating an organic phase, drying with anhydrous magnesium sulfate, and removing the solvent under reduced pressure to obtain a crude product; purification by silica gel column chromatography using a methylene chloride/n-heptane mixed solvent as a mobile phase crude product gave the intermediate M-1(6.09 g; yield 75%) as a white solid product
Using a method similar to the synthesis of intermediate a, using reactant H shown in table 7 instead of intermediate a-4, and reactant I shown in table 7 instead of 3-bromocarbazole, intermediates 2-29 were synthesized:
table 7: synthesis of intermediates 2 to 29
Figure BDA0002626325870000382
Figure BDA0002626325870000391
Figure BDA0002626325870000401
Figure BDA0002626325870000411
Figure BDA0002626325870000421
Figure BDA0002626325870000422
Adding intermediate M-1(6.09 g; mmol), 2- (3-bromophenyl) dibenzofuran (4.7 g; 14.6mmol), cuprous iodide (0.3 g; 2.4mmol), potassium carbonate (3.7 g; 26.7mmol), 1, 10-phenanthroline (0.9 g; 4.8mmol), 18-crown-6-ether (0.3 g; 1.2mmol) and dimethylformamide (40mL) into a flask, heating to 145 ℃ under the protection of nitrogen, and stirring for 8 hours; cooling to room temperature, adding dichloromethane (80mL) and water (100mL) into the reaction solution, separating, washing the organic phase with water, adding anhydrous magnesium sulfate, drying, and removing the solvent under reduced pressure to obtain a crude product; the crude product was purified by column chromatography on silica gel using a methylene chloride/n-heptane system and then purified by recrystallization using a methylene chloride/ethyl acetate system to obtain the product compound 20(4.5 g; yield 50%) as a white solid.
Using a procedure similar to that used for the synthesis of compound 20, the compounds shown in Table 8 below were synthesized using reactant J in Table 8 instead of intermediate M-1 and reactant K in Table 8 instead of 2- (3-bromophenyl) dibenzofuran:
table 8: structures and starting materials for part of the Compounds
Figure BDA0002626325870000423
Figure BDA0002626325870000431
Figure BDA0002626325870000441
Figure BDA0002626325870000451
Figure BDA0002626325870000452
Adding the intermediate 6(6 g; 12.0mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (3.5 g; 13.1mmol), 4-dimethylaminopyridine (0.7 g; 6.0mmol), cesium carbonate (3.9 g; 12.0mmol) and dimethyl sulfoxide (80mL) into a round-bottomed flask, stirring and heating to 100 ℃ under the protection of nitrogen, and reacting for 12 hours; cooling to room temperature after the reaction is finished, filtering, leaching a filter cake by using water and ethanol, and drying to obtain a crude product; the crude product was purified by recrystallization using a toluene/n-heptane system to give compound 26(5.2 g; yield 60%) as a pale yellow solid.
Using a procedure similar to that used for the synthesis of compound 26, the compounds shown in Table 9 below were synthesized using reactant L in Table 9 instead of intermediate M-6 and reactant M instead of 2-chloro-4, 6-diphenyl-1, 3, 5-triazine:
table 9: starting materials and structures of partial compounds
Figure BDA0002626325870000453
Figure BDA0002626325870000461
Figure BDA0002626325870000471
Mass spectrometry analysis of the above compounds gave the following data as shown in table 10 below:
table 10: mass spectral data of partial compounds
Compound 2 m/z＝654.3[M+H]+ Compound 89 m/z＝733.3[M+H]+
Compound 6 m/z＝607.3[M+H]+ Compound 99 m/z＝634.3[M+H]+
Compound 12 m/z＝730.3[M+H]+ Compound 103 m/z＝694.3[M+H]+
Compound 14 m/z＝725.3[M+H]+ Compound 107 m/z＝885.4[M+H]+
Compound 20 m/z＝744.3[M+H]+ Compound 110 m/z＝839.3[M+H]+
Compound 21 m/z＝760.3[M+H]+ Compound 113 m/z＝809.4[M+H]+
Compound 26 m/z＝733.3[M+H]+ Compound 125 m/z＝746.3[M+H]+
Compound 31 m/z＝704.3[M+H]+ Compound 131 m/z＝758.3[M+H]+
Compound 33 m/z＝743.3[M+H]+ Compound 136 m/z＝809.4[M+H]+
Compound 38 m/z＝668.3[M+H]+ Compound 142 m/z＝668.3[M+H]+
Compound 57 m/z＝678.3[M+H]+ Compound 147 m/z＝706.3[M+H]+
Compound 78 m/z＝770.4[M+H]+ Compound 153 m/z＝823.3[M+H]+
Compound 83 m/z＝678.3[M+H]+ Compound 157 m/z＝732.3[M+H]+
Compound 88 m/z＝822.4[M+H]+ Compound 222 m/z＝756.3[M+H]+
Compound 95 m/z＝672.3[M+H]+
Nuclear magnetic data for some of the above example compounds:
compound 2:1HNMR(CD2Cl2,400MHz)δ(ppm):8.26(d,1H),7.91-7.84(m,3H),7.79-7.49(m,4H),7.61-7.52(m,9H),7.42-7.38(m,3H),7.33-7.24(m,5H),2.80(d,2H),2.71(d,2H),2.15(s,1H),2.14(s,1H),1.93(s,2H),1.72(t,4H),1.42(s,2H).
compound 20:1HNMR(CD2Cl2,400MHz)δ(ppm):8.29(d,1H),8.12(s,1H),8.06(s,1H),8.01(d,1H),7.96-7.94(m,2H),7.88-7.83(m,2H),7.78(d,1H),7.71(d,1H),7.61-7.54(m,5H),7.52-7.45(m,3H),7.42-7.36(m,2H),7.34-7.20(m,5H),7.12(d,1H),7.08(d,1H),2.83(d,2H),2.74(d,2H),2.16(s,1H),2.10(s,1H),1.95(s,2H),1.75(t,4H),1.40(s,2H).
compound 26:1HNMR(CD2Cl2,400MHz)δ(ppm):8.53-8.51(m,4H),8.36(s,1H),8.26(d,2H),8.05(d,1H),7.95(m,1H),7.88-7.84(m,2H),7.79(d,1H),7.71(d,1H),7.58-7.54(m,7H),7.43(d,1H),7.42-7.38(m,2H),7.27(t,1H),7.00(d,1H),6.90(d,1H),2.86(d,2H),2.74(d,2H),2.15(s,1H),2.09(s,1H),1.95(s,2H),1.72(t,4H),1.43(s,2H).
compound 99:1HNMR(CD2Cl2,400MHz)δ(ppm):8.36(s,1H),8.17(s,1H),8.07(m,1H),7.90(t,2H),7.79(d,1H),7.62(s,1H),7.52(t,1H),7.47-7.40(m,4H),7.30-7.24(m,6H),7.02-6.94(m,2H),2.84(d,2H),2.71(d,2H),2.13(s,1H),2.11(s,1H),1.90(s,2H),1.74(t,4H),1.38(s,2H),1.33(s,9H).
preparation and performance evaluation of organic electroluminescent device
Example 1: green organic electroluminescent device
The green organic electroluminescent device was fabricated using the following method:
the anode was prepared by the following procedure: the thickness of ITO is set as
Figure BDA0002626325870000481
The ITO substrate of (1) was cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness), and prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern by using a photolithography process, and UV ozone and O were used2:N2Plasma is used for surface treatment to increase the work function of the anode, and an organic solvent can be used for cleaning the surface of the ITO substrate to remove impurities and oil stains on the surface of the ITO substrate. It should be noted that the ITO substrate may also be cut into other sizes according to actual needs, and the size of the ITO substrate in this application is not particularly limited.
F4-TCNQ was vacuum-evaporated onto an experimental substrate (anode) to a thickness of
Figure BDA0002626325870000482
And HT-01 is vapor-deposited on the hole injection layer to form a Hole Injection Layer (HIL) having a thickness of
Figure BDA0002626325870000483
The first hole transport layer of (1).
Vacuum evaporating HT-02 on the first hole transport layer to a thickness of
Figure BDA0002626325870000484
The second hole transport layer of (1).
On the second hole transport layer, compound 2: GH-n1: ir (ppy)3In a ratio of 50%: 45%: 5% (evaporation rate) of vapor deposition to form a film having a thickness of
Figure BDA0002626325870000485
Green emitting layer (EML).
ET-01 and LiQ are mixed according to the weight ratio of 1:1 and evaporated to form
Figure BDA0002626325870000486
A thick Electron Transport Layer (ETL), and depositing LiQ on the electron transport layer to form a layer with a thickness of
Figure BDA0002626325870000487
And then magnesium (Mg) and silver (Ag) are mixed in a ratio of 1: 9 is vacuum-evaporated on the electron injection layer to a thickness of
Figure BDA0002626325870000488
The cathode of (1).
The thickness of the vapor deposition on the cathode is set to
Figure BDA0002626325870000489
Forming an organic capping layer (CPL), thereby completing the fabrication of the organic light emitting device.
Example 2 to example 16
An organic electroluminescent device was produced in the same manner as in example 1, except that the compound shown in the column of compound N in table 10 was used in place of compound 2 in example 1. Wherein, in the organic light emitting layer of the prepared organic electroluminescent device, the ratio of compound N: GH-n1 Ir (ppy)350 percent, 45 percent and 5 percent. For example, in practiceIn example 2, compound N was compound 6, and compound 6 was used instead of compound 2 in example 1 to prepare an organic electroluminescent device.
Comparative example 1 to comparative example 4
An organic electroluminescent device was produced in the same manner as in example 1, except that the compounds a to D shown in the following table were used instead of the compound 2 in example 1 in forming the light-emitting layer. For example, in comparative example 1, in the organic light emitting layer of the organic electroluminescent device prepared, compound a: GH-n1 Ir (ppy)3＝50％:45％:5％。
The structures of the materials used in examples 1 to 16 and comparative examples 1 to 4 are as follows:
Figure BDA00026263258700004810
Figure BDA0002626325870000491
the organic electroluminescent devices prepared in examples 1 to 16 and comparative examples 1 to 4 were each controlled at 20mA/cm2The performance test was performed under the conditions of (1), and the test results are shown in table 11 below.
Table 11: performance test results of organic electroluminescent device
Figure BDA0002626325870000492
Figure BDA0002626325870000501
As can be seen from the data shown in table 11, compared to the organic electroluminescent devices prepared in comparative examples 1 to 4, the organic electroluminescent devices prepared in examples 1 to 16 have improved light emitting efficiency and increased device lifetime by at least 50% under the premise of similar driving voltages. Therefore, when the nitrogen-containing compound of the present application is used as an organic light emitting layer material of an organic electroluminescent device, particularly as a host material of an organic light emitting layer of the organic electroluminescent device, the efficiency performance and lifetime of the organic electroluminescent device can be improved.
Example 17: red organic electroluminescent device
The anode was prepared by the following procedure: the thickness of ITO is set as
Figure BDA0002626325870000502
The ITO substrate of (1) was cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness), and prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern by using a photolithography process, and UV ozone and O were used2:N2Plasma is used for surface treatment to increase the work function of the anode, and an organic solvent can be used for cleaning the surface of the ITO substrate to remove impurities and oil stains on the surface of the ITO substrate. It should be noted that the ITO substrate may also be cut into other sizes according to actual needs, and the size of the ITO substrate in this application is not particularly limited.
F4-TCNQ was vacuum-deposited on an experimental substrate (anode) to a thickness of
Figure BDA0002626325870000503
And HT-01 is vapor-deposited on the hole injection layer to form a Hole Injection Layer (HIL) having a thickness of
Figure BDA0002626325870000504
The first hole transport layer of (1).
Vacuum evaporating HT-03 on the first hole transport layer to a thickness of
Figure BDA0002626325870000505
The second hole transport layer of (1).
On the second hole transport layer, compound 26: ir (piq)2(acac) at 95%: 5% (evaporation rate) of vapor deposition to form a film having a thickness of
Figure BDA0002626325870000506
Red hair ofAn optical layer (EML).
ET-01 and LiQ are mixed according to the weight ratio of 1:1 and evaporated to form
Figure BDA0002626325870000507
A thick Electron Transport Layer (ETL), and depositing LiQ on the electron transport layer to form a layer with a thickness of
Figure BDA0002626325870000508
And then magnesium (Mg) and silver (Ag) are mixed in a ratio of 1: 9 is vacuum-evaporated on the electron injection layer to a thickness of
Figure BDA0002626325870000509
The cathode of (1).
The thickness of the vapor deposition on the cathode is set to
Figure BDA0002626325870000511
Forming an organic capping layer (CPL), thereby completing the fabrication of the organic light emitting device.
Example 18 example 29
An organic electroluminescent device was produced in the same manner as in example 17 except that the compound shown in the column of compound M in table 11 was used in place of compound 26 in example 17. Wherein, in the organic light emitting layer of the prepared organic electroluminescent device, the ratio of compound M: ir (piq)2(acac): 95%: 5%. For example, in example 18, compound M was compound 88, and compound 88 was used instead of compound 26 in example 17 to prepare an organic electroluminescent device.
Comparative examples 5 to 9
An organic electroluminescent device was produced in the same manner as in example 17, except that the compounds E to H shown in the following table were used in place of the compound 26 in example 17 in forming the light-emitting layer. For example, in comparative example 5, in the organic light emitting layer of the organic electroluminescent device prepared, the compound E: ir (piq)2(acac)＝95％:5％。
Some of the material structures used in the above examples and comparative examples are as follows:
Figure BDA0002626325870000512
the organic electroluminescent devices prepared in examples 17 to 29 and comparative examples 5 to 8 were each controlled at 20mA/cm2The performance test was performed under the conditions of (1), and the test results are shown in table 12 below.
Table 12: performance test results of organic electroluminescent device
Figure BDA0002626325870000513
Figure BDA0002626325870000521
As can be seen from the data shown in table 12, compared with the organic electroluminescent devices prepared in comparative examples 5 to 8, the driving voltage and the light-emitting efficiency of the organic electroluminescent devices prepared in examples 17 to 29 are improved to some extent, the light-emitting efficiency of the devices is improved by at least 10%, and the lifetime is improved by at least 27%. Therefore, when the nitrogen-containing compound of the present application is used as an organic light emitting layer material of an organic electroluminescent device, particularly as a host material of an organic light emitting layer of the organic electroluminescent device, the efficiency performance and lifetime performance of the organic electroluminescent device can be improved.
In the compound of the present application, adamantane as a part of the core of the nitrogen-containing compound is screwed to the condensed fluorenyl group and linked to the carbazolyl group, so that the compound as a whole has high rigidity and the nitrogen-containing compound of the present application has a high first triplet level, and the carbazole ring conjugated to the condensed fluorenyl group in the compound has good hole transport ability, and therefore, the nitrogen-containing compound of the present application is suitable as a light-emitting layer host material in an organic electroluminescent device. The nitrogen-containing compound has high hole mobility, is helpful for promoting the transmission balance of holes and electrons in the light-emitting layer, and improves the efficiency performance of the organic electroluminescent device. The recombination rate of electrons and holes in the organic light-emitting layer is improved, and the electrons are reduced or prevented from passing through the organic light-emitting layer and being transmitted to the hole transport layer, so that the hole transport layer material can be effectively protected from the impact of the electrons, and the service life of the organic electroluminescent device is prolonged.
Alternative embodiments of the present application have been described in detail with reference to the accompanying drawings, however, the present application is not limited to the details of the above embodiments, and various simple modifications may be made to the technical solution of the present application within the technical concept of the present application, and these simple modifications are within the scope of the present application.
It should be noted that, in the foregoing embodiments, various features described in the above embodiments may be combined in any suitable manner, and in order to avoid unnecessary repetition, various possible combinations are not described in the present application.
In addition, any combination of the various embodiments of the present application is also possible, and the same should be considered as disclosed in the present application as long as it does not depart from the idea of the present application.

Claims (17)

1. A nitrogen-containing compound, wherein the nitrogen-containing compound has a structural formula shown in chemical formula 1:
Figure FDA0002626325860000011
wherein the ring A is a fused aromatic ring with ring-forming carbon atoms of 10-14 or a fused heteroaromatic ring with ring-forming carbon atoms of 8-12, and the ring A is not a carbazole ring;
the ring B is a benzene ring, a fused aromatic ring with ring-forming carbon atoms of 10-14 or a fused heteroaromatic ring with ring-forming carbon atoms of 8-12;
the ring C is a benzene ring or a condensed aromatic ring with 10-14 ring-forming carbon atoms;
R1、R2、R3、R4are identical or different from each other and are each independently selected from deuterium, a halogen group, a cyano group, a carbanoA haloalkyl group having 1 to 12 carbon atoms, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an arylthio group having 6 to 20 carbon atoms, and an arylsilyl group having 6 to 18 carbon atoms;
n1represents a substituent R1Number of (2), n2Represents a substituent R2Number of (2), n3Represents a substituent R3Number of (2), n4Represents a substituent R4Number of (2), n1、n2、n3、n4Are the same or different from each other and are each independently selected from 0, 1,2, 3 or 4;
when n is1When greater than 1, any two of R1Same or different when n2When greater than 1, any two of R2Same or different when n3When greater than 1, any two of R3Same or different when n4When greater than 1, any two of R4The same or different;
w is selected from substituted or unsubstituted aryl with 6-40 carbon atoms and substituted or unsubstituted heteroaryl with 3-40 carbon atoms;
the substituents in W, which may be the same or different from each other, are each independently selected from the group consisting of: deuterium, a halogen group, a cyano group, an alkyl group having 1 to 12 carbon atoms, a haloalkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a heterocycloalkyl group having 2 to 10 carbon atoms, an aralkyl group having 7 to 10 carbon atoms, a heteroaralkyl group having 4 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms optionally substituted with 0, 1,2 or 3 substituents selected from deuterium, fluorine, chlorine, bromine, cyano and alkyl, a heteroaryl group having 3 to 30 carbon atoms optionally substituted with 0, 1,2 or 3 substituents selected from deuterium, fluorine, chlorine, bromine, cyano and alkyl, an alkoxy group having 1 to 12 carbon atoms, an alkylthio group having 1 to 12 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an arylsilyl group having 6 to 30 carbon atoms, aryloxy group having 6 to 20 carbon atoms, arylthio group having 6 to 20 carbon atoms;
in the W, when two substituents are present on the same atom, optionally, the two substituents attached to the same atom are linked to each other to form a saturated or unsaturated 5-to 18-membered aliphatic ring or a 5-to 18-membered aromatic ring with the atom to which they are commonly attached.
2. The nitrogen-containing compound according to claim 1, wherein the ring a is a naphthalene ring, an anthracene ring, a phenanthrene ring, a dibenzofuran ring, a dibenzothiophene ring, a thianthrene ring, a phenoxathiin ring, a dibenzodioxin ring, 10H-phenothiazine, or 10H-phenoxazine; the ring B is a benzene ring, a naphthalene ring, a quinoline ring or an isoquinoline ring; the ring C is a benzene ring, a naphthalene ring, an anthracene ring or a phenanthrene ring.
3. The nitrogen-containing compound according to claim 1 or 2, wherein the structural formula of the nitrogen-containing compound is represented by any one of chemical formulas (f-1) to (f-16):
Figure FDA0002626325860000021
4. the nitrogen-containing compound according to any one of claims 1 to 3, wherein the compound represented by the formula (1)
Figure FDA0002626325860000031
Selected from the following structures:
Figure FDA0002626325860000032
5. the nitrogen-containing compound according to any one of claims 1 to 4, wherein W is
Figure FDA0002626325860000033
Wherein each L is independently selected from a single bond, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, and a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; ar is selected from substituted or unsubstituted heteroaryl with 3-30 carbon atoms and substituted or unsubstituted aryl with 6-30 carbon atoms;
the substituent in the L and the substituent in the Ar are one or more, and the substituents in the Ar and the L are the same or different and are respectively and independently selected from deuterium, a halogen group, a cyano group, an aryl group with 6-20 carbon atoms, a substituted or unsubstituted heteroaryl group with 3-20 carbon atoms, a halogenated alkyl group with 1-12 carbon atoms, an alkyl group with 1-12 carbon atoms, a cycloalkyl group with 3-12 carbon atoms, an alkoxy group with 1-12 carbon atoms, an alkylthio group with 1-12 carbon atoms, a trialkylsilyl group with 3-12 carbon atoms, an aryloxy group with 6-20 carbon atoms, an arylthio group with 6-20 carbon atoms and an arylsilyl group with 6-18 carbon atoms;
when two substituents are present on the same atom, optionally, the two substituents attached to the same atom can be linked to each other to form a saturated or unsaturated 5-to 13-membered aliphatic ring or a 5-to 13-membered aromatic ring with the atoms to which they are commonly attached.
6. The nitrogen-containing compound according to claim 5, wherein L is a single bond, a substituted or unsubstituted arylene group having 6 to 25 carbon atoms, or a substituted or unsubstituted heteroarylene group having 5 to 14 carbon atoms.
7. The nitrogen-containing compound according to claim 5, wherein L is selected from a single bond, or a group consisting of groups represented by the formulae j-1 to j-13:
Figure FDA0002626325860000034
Figure FDA0002626325860000041
wherein M is2Selected from a single bond or
Figure FDA0002626325860000042
Q1～Q5Each independently selected from N or C (J)5) And Q is1～Q5At least one is selected from N; when Q is1～Q5Two or more of them are selected from C (J)5) When, two arbitrary J5The same or different;
Q6～Q13each independently selected from N or C (J)6) And Q is6～Q13At least one is selected from N; when Q is6～Q13Two or more of them are selected from C (J)6) When, two arbitrary J6The same or different;
Q14～Q23each independently selected from N, C or C (J)7) And Q is14～Q23At least one is selected from N; when Q is14～Q23Two or more of them are selected from C (J)7) When, two arbitrary J7The same or different;
Q24～Q33each independently selected from N, C or C (J)8) And Q is24～Q33At least one is selected from N; when Q is24～Q33Two or more of them are selected from C (J)8) When, two arbitrary J8The same or different;
E1～E14、J5～J8each independently selected from: hydrogen, deuterium, a halogen group, a cyano group, a heteroaryl group having 3 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, a trialkylsilyl group having 3 to 9 carbon atoms, an arylsilyl group having 8 to 12 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a cycloalkyl group having 2 carbon atoms10 heterocycloalkyl group, 4 to 10 heterocycloalkenyl group, 1 to 10 alkoxy group, 1 to 10 alkylthio group, 6 to 18 aryloxy group, and 6 to 18 arylthio group;
e1～e14with erIs represented by1～E14With ErR is a variable and is an arbitrary integer of 1 to 14, erRepresents a substituent ErThe number of (2); when r is selected from 1,2, 3,4, 5, 6, 9, 13 or 14, erSelected from 1,2, 3 or 4; when r is selected from 7 or 11, erSelected from 1,2, 3,4, 5 or 6; when r is 12, erSelected from 1,2, 3,4, 5, 6 or 7; when r is selected from 8 or 10, erSelected from 1,2, 3,4, 5, 6, 7 or 8; when e isrWhen greater than 1, any two of ErThe same or different;
K3selected from O, S, Se, N (E)15)、C(E16E17)、Si(E18E19) (ii) a Wherein each E15、E16、E17、E18And E19Each independently selected from: hydrogen, aryl with 6-20 carbon atoms, heteroaryl with 3-20 carbon atoms, alkyl with 1-10 carbon atoms and cycloalkyl with 3-10 carbon atoms;
or, optionally, E above16And E17Are linked to each other to form a 5-to 13-membered aliphatic ring or a 5-to 13-membered aromatic ring with the atoms to which they are commonly linked;
or, optionally, E above18And E19Are linked to each other to form a 5-to 13-membered aliphatic ring or a 5-to 13-membered aromatic ring with the atoms to which they are commonly linked;
each K4Independently selected from single bond, O, S, Se, N (E)20)、C(E21E22)、Si(E23E24) (ii) a Wherein each E20、E21、E22、E23、E24Each independently selected from: hydrogen, aryl group having 6 to 20 carbon atoms, heteroaryl group having 3 to 20 carbon atoms, alkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atomsA heterocycloalkyl group having 2 to 10 carbon atoms;
or, optionally, E above21And E22Are linked to each other to form a 5-to 13-membered aliphatic ring or a 5-to 13-membered aromatic ring with the atoms to which they are commonly linked;
or, optionally, E above23And E24Are linked to each other to form a 5-to 13-membered aliphatic ring or a 5-to 13-membered aromatic ring with the atoms to which they are commonly linked.
8. The nitrogen-containing compound according to claim 5, wherein L is selected from the group consisting of a single bond, unsubstituted L1Substituted L1Wherein, L is unsubstituted1Selected from the group consisting of:
Figure FDA0002626325860000051
wherein, substituted L1Is unsubstituted L1Substituted by one or more groups selected from deuterium, fluorine, chlorine, bromine, cyano, alkyl having 1 to 4 carbon atoms, haloalkyl having 1 to 4 carbon atoms, trialkylsilyl having 3 to 9 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, aryl having 6 to 15 carbon atoms and heteroaryl having 3 to 12 carbon atoms, and when substituted L1When the number of the substituent(s) is plural, any two of the substituents may be the same or different.
9. The nitrogen-containing compound according to any one of claims 5 to 8, wherein Ar is selected from a substituted or unsubstituted aryl group having 6 to 25 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 25 carbon atoms; the substituents in Ar are one or more, the same or different from each other, and each independently selected from deuterium, fluorine, chlorine, a cyano group, an aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 6 carbon atoms, a haloalkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylthio group having 1 to 6 carbon atoms, a cycloalkyl group having 5 to 10 carbon atoms, a trialkylsilyl group having 3 to 9 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an arylthio group having 6 to 20 carbon atoms, and an arylsilyl group having 6 to 18 carbon atoms.
10. The nitrogen-containing compound according to any one of claims 5 to 8, wherein Ar is selected from the group consisting of groups represented by chemical formulae i-1 to i-18:
Figure FDA0002626325860000052
Figure FDA0002626325860000061
wherein M is1Selected from a single bond or
Figure FDA0002626325860000062
G1～G5Each independently selected from N or C (F)1) And G is1～G5At least one is selected from N; when G is1～G5Two or more of C (F)1) When, two arbitrary F1The same or different;
G6～G13each independently selected from N or C (F)2) And G is6～G13At least one is selected from N; when G is6～G13Two or more of C (F)2) When, two arbitrary F2The same or different;
G14～G23each independently selected from N or C (F)3) And G is14～G23At least one is selected from N; when G is14～G23Two or more of C (F)3) When, two arbitrary F3The same or different; or, optionally, two adjacent F3Mutually connected to form a 5-to 10-membered aromatic ring or a 5-to 10-membered heteroaromatic ring;
G24～G33each independently selected from N or C (F)4) And G is24～G33At least one is selected from N; when G is24～G33Two or more of C (F)4) When, two arbitrary F4The same or different; or, optionally, two adjacent F4Mutually connected to form a 5-to 10-membered aromatic ring or a 5-to 10-membered heteroaromatic ring;
G34～G37each independently selected from N or C (F)5) When G is34～G37Two or more of C (F)5) When, two arbitrary F5The same or different; or, optionally, two adjacent F5Mutually connected to form a 5-to 10-membered aromatic ring or a 5-to 10-membered heteroaromatic ring;
G38～G45each independently selected from N or C (F)6) And G is38～G45At least one is selected from N; when G is38～G45Two or more of C (F)6) When, two arbitrary F6The same or different;
G46～G53each independently selected from N or C (F)7) And G is46～G53At least one is selected from N; when G is46～G53Two or more of them are selected from C (F)7) When, two arbitrary F7The same or different; or, optionally, two adjacent F7Mutually connected to form a 5-to 10-membered aromatic ring or a 5-to 10-membered heteroaromatic ring;
D1selected from the group consisting of hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms and alkylthio having 1 to 10 carbon atoms;
D2～D9、D21each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, and a carbon atomCycloalkyl having a sub-number of 3 to 10, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, heteroaryl having 3 to 18 carbon atoms;
D10～D20、F1～F7each independently selected from: hydrogen, deuterium, fluorine, chlorine, bromine, cyano, trialkylsilyl having 3 to 12 carbon atoms, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 10 carbon atoms, alkylthio having 1 to 10 carbon atoms, an aryl group having 6 to 18 carbon atoms and a heteroaryl group having 3 to 18 carbon atoms, which are optionally substituted with 0, 1,2 or 3 substituents selected from deuterium, fluorine, chlorine, cyano, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an alkylamino group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 7 carbon atoms, an aryl group having 6 to 15 carbon atoms, a heteroaryl group having 3 to 12 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a haloalkyl group having 1 to 4 carbon atoms, an alkylsilyl group having 3 to 9 carbon atoms;
d1～d21with dkIs represented by1～D21With DkK is a variable and represents an arbitrary integer of 1 to 21, dkRepresents a substituent DkThe number of (2); wherein, when k is selected from 5 or 17, dkSelected from 1,2 or 3; when k is selected from 2, 7, 8, 12, 15, 16, 18 or 21, dkSelected from 1,2, 3 or 4; when k is selected from 1,3, 4,6, 9 or 14, dkSelected from 1,2, 3,4 or 5; when k is 13, dkSelected from 1,2, 3,4, 5 or 6; when k is selected from 10 or 19, dkSelected from 1,2, 3,4, 5, 6 or 7; when k is 20, dkSelected from 1,2, 3,4, 5, 6, 7 or 8; when k is 11, dkSelected from 1,2, 3,4, 5, 6, 7, 8 or 9; and when d iskWhen greater than 1, any two DkThe same or different;
K1and K6Each independently selected from O, S, N (D)22)、C(D23D24)、Si(D28D29) (ii) a It is composed ofIn (1), each D22、D23、D24、D28、D29Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms;
or, optionally, D above23And D24Are linked to each other to form a 5-to 14-membered aliphatic ring or a 5-to 14-membered aromatic ring with the atoms to which they are commonly linked;
or, optionally, D above28And D29Are linked to each other to form a 5-to 14-membered aliphatic ring or a 5-to 14-membered aromatic ring with the atoms to which they are commonly linked;
K2selected from the group consisting of single bond, O, S, N (D)25)、C(D26D27)、Si(D30D31) (ii) a Wherein each D25、D26、D27、D30、D31Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms,
or, optionally, D above26And D27Are linked to each other to form a 5-to 14-membered aliphatic ring or a 5-to 14-membered aromatic ring with the atoms to which they are commonly linked;
or, optionally, D above30And D31Are linked to each other to form a 5-to 14-membered aliphatic ring or a 5-to 14-membered aromatic ring with the atoms to which they are commonly linked;
K5selected from O, S, Se, N (D)32)、C(D33D34) Wherein D is32、D33And D34Each independently selected from: an aryl group having 6 to 18 carbon atoms, a heteroaryl group having 3 to 18 carbon atoms, an alkyl group having 1 to 10 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms.
11. The nitrogen-containing compound according to any one of claims 5 to 8, wherein Ar is selected from unsubstituted Ar1Or substituted Ar1Wherein, Ar is unsubstituted1Selected from the group consisting of:
Figure FDA0002626325860000071
Figure FDA0002626325860000081
wherein Z is1And Z2Each independently selected from hydrogen, aryl having 6 to 20 carbon atoms, and heteroaryl having 3 to 20 carbon atoms; any two Z1Identical or different, any two Z2The same or different;
wherein, substituted Ar1Is unsubstituted Ar1A group substituted by one or more groups selected from deuterium, fluorine, chlorine, cyano, C1-4 alkyl, C1-4 alkoxy, C1-4 alkylamino, C3-7 cycloalkyl, C6-14 aryl, C3-12 heteroaryl, C1-4 alkylthio, C1-4 haloalkyl, C3-9 alkylsilyl, and when Ar is Ar1When the number of the substituent(s) is plural, any two of the substituents may be the same or different.
12. The nitrogen-containing compound according to claim 11, wherein Z1And Z2Each independently selected from: hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthryl, substituted or unsubstituted phenanthryl, substituted or unsubstituted perylene, substituted or unsubstituted fluoranthryl, substituted or unsubstituted anthryl
Figure FDA0002626325860000082
A substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzothienyl group, a substituted or unsubstituted diphenyl groupA furyl group, a substituted or unsubstituted N-phenylcarbazolyl group, a substituted or unsubstituted carbazol-9-ylphenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzoxazine, a substituted or unsubstituted triphenylene group;
Z1and Z2Each substituent in (a) is independently selected from: fluorine, deuterium, cyano, trifluoromethyl, trimethylsilyl, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, trifluoromethyl, cyclopentyl, cyclohexyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, quinolinyl, isoquinolinyl, and carbazolyl.
13. The nitrogen-containing compound according to any one of claims 1 to 12, wherein R is1、R2、R3、R4The aryl group is the same or different and is independently selected from deuterium, a halogen group, a cyano group, a halogenated alkyl group with 1-4 carbon atoms, an alkenyl group with 2-6 carbon atoms, an alkynyl group with 2-6 carbon atoms, a cycloalkyl group with 5-10 carbon atoms, a heterocycloalkyl group with 4-6 carbon atoms, an alkoxy group with 1-4 carbon atoms, an alkylthio group with 1-4 carbon atoms, a trialkylsilyl group with 3-9 carbon atoms, an aryl group with 6-15 carbon atoms, a heteroaryl group with 3-12 carbon atoms, an aryloxy group with 6-15 carbon atoms, an arylthio group with 6-15 carbon atoms and a triphenylsilyl group; n is1、n2、n3、n4Are the same or different from each other and are each independently selected from 0, 1,2, 3 or 4.
14. The nitrogen-containing compound of claim 1, wherein the nitrogen-containing compound is selected from the group consisting of:
Figure FDA0002626325860000091
Figure FDA0002626325860000101
Figure FDA0002626325860000111
Figure FDA0002626325860000121
Figure FDA0002626325860000131
Figure FDA0002626325860000141
Figure FDA0002626325860000151
15. an organic electroluminescent device comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode;
the functional layer comprises the nitrogen-containing compound according to any one of claims 1 to 14.
16. The organic electroluminescent device according to claim 15, wherein the functional layer comprises a hole injection layer, a hole transport layer, an organic light emitting layer containing the nitrogen-containing compound according to any one of claims 1 to 14, an electron transport layer, and an electron injection layer.
17. An electronic device comprising the organic electroluminescent element as claimed in claim 15 or 16.
CN202010798721.7A 2020-04-07 2020-08-10 Nitrogen-containing compound, organic electroluminescent element using same, and electronic device Active CN111925315B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/CN2020/122273 WO2021203673A1 (en) 2020-04-07 2020-10-20 Nitrogen containing compound, organic electroluminescent device using same, and electronic device

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN2020102662026 2020-04-07
CN202010266202 2020-04-07

Publications (2)

Publication Number Publication Date
CN111925315A CN111925315A (en) 2020-11-13
CN111925315B true CN111925315B (en) 2021-06-01

Family

ID=73307261

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202010798721.7A Active CN111925315B (en) 2020-04-07 2020-08-10 Nitrogen-containing compound, organic electroluminescent element using same, and electronic device

Country Status (2)

Country Link
CN (1) CN111925315B (en)
WO (1) WO2021203673A1 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111848501B (en) * 2020-05-08 2021-06-01 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, and electronic element and electronic device using same
CN112142548B (en) * 2020-09-30 2021-09-24 陕西莱特光电材料股份有限公司 Organic compound, and electronic element and electronic device using same
CN112480011B (en) * 2020-12-04 2022-09-13 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, organic electroluminescent device, and electronic device
CN114122288A (en) * 2021-11-12 2022-03-01 长春海谱润斯科技股份有限公司 Organic electroluminescent device comprising light extraction layer
CN116396230A (en) * 2022-09-01 2023-07-07 陕西莱特光电材料股份有限公司 Organic compound, electronic component, and electronic device

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110615759A (en) * 2019-09-25 2019-12-27 陕西莱特光电材料股份有限公司 Compound, photoelectric conversion device, and electronic device
WO2020046049A1 (en) * 2018-08-31 2020-03-05 주식회사 엘지화학 Novel compound and organic light emitting device using same
WO2020045924A1 (en) * 2018-08-29 2020-03-05 주식회사 엘지화학 Novel compound and organic light emitting diode using same
CN111018797A (en) * 2019-12-26 2020-04-17 陕西莱特光电材料股份有限公司 Organic compound, electronic element containing the same, and electronic device
CN111454197A (en) * 2019-12-31 2020-07-28 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, organic electroluminescent device, and electronic device

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020045924A1 (en) * 2018-08-29 2020-03-05 주식회사 엘지화학 Novel compound and organic light emitting diode using same
WO2020046049A1 (en) * 2018-08-31 2020-03-05 주식회사 엘지화학 Novel compound and organic light emitting device using same
CN110615759A (en) * 2019-09-25 2019-12-27 陕西莱特光电材料股份有限公司 Compound, photoelectric conversion device, and electronic device
CN111018797A (en) * 2019-12-26 2020-04-17 陕西莱特光电材料股份有限公司 Organic compound, electronic element containing the same, and electronic device
CN111454197A (en) * 2019-12-31 2020-07-28 陕西莱特光电材料股份有限公司 Nitrogen-containing compound, organic electroluminescent device, and electronic device

Also Published As

Publication number Publication date
WO2021203673A1 (en) 2021-10-14
CN111925315A (en) 2020-11-13

Similar Documents

Publication Publication Date Title
CN111454197B (en) Nitrogen-containing compound, organic electroluminescent device, and electronic device
CN111961038B (en) Compound, organic electroluminescent device and electronic device
CN111925315B (en) Nitrogen-containing compound, organic electroluminescent element using same, and electronic device
CN111646983B (en) Nitrogen-containing compound, organic electroluminescent device, and electronic device
CN111848588B (en) Organic compound, and electronic element and electronic device using same
CN112159348B (en) Nitrogen-containing compound, electronic component, and electronic device
CN112300055B (en) Nitrogen-containing compound, electronic component, and electronic device
CN112876486B (en) Organic compound, electronic element comprising same and electronic device
WO2021135725A1 (en) Organic compound, electronic device and electronic apparatus using same
CN111004226B (en) Organic electroluminescent material, intermediate thereof, electronic device, and electronic apparatus
CN112661709B (en) Nitrogen-containing organic compound, and electronic element and electronic device using same
CN111662241B (en) Organic compound, electronic element, and electronic device
CN114133400B (en) Organic compound, and electronic component and electronic device using same
CN111848492B (en) Organic compound, and device and electronic device using same
CN112341343A (en) Organic compound, electronic element containing organic compound and electronic device
CN113636944A (en) Organic compound, electronic element containing organic compound and electronic device
CN113735861B (en) Organic compound, and electronic component and electronic device using same
CN113105462B (en) Organic compound, and electronic element and electronic device using same
CN112538021B (en) Nitrogen-containing compound, electronic component, and electronic device
CN111995564B (en) Organic compound, electronic element, and electronic device
CN113372321A (en) Organic compound, and electronic device and apparatus comprising the same
CN113292566B (en) Organic compound, application thereof, organic electroluminescent device using organic compound and electronic device
CN114075191B (en) Organic electroluminescent material, electronic element, and electronic device
CN113788847A (en) Organic compound, and electronic element and electronic device using same
CN114075203A (en) Organic compound, and organic electroluminescent device and electronic device using same

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
GR01 Patent grant
GR01 Patent grant