CN106831313A - A kind of compound and its organic electroluminescence device with triaryl naphthalene - Google Patents

A kind of compound and its organic electroluminescence device with triaryl naphthalene Download PDF

Info

Publication number
CN106831313A
CN106831313A CN201710055510.2A CN201710055510A CN106831313A CN 106831313 A CN106831313 A CN 106831313A CN 201710055510 A CN201710055510 A CN 201710055510A CN 106831313 A CN106831313 A CN 106831313A
Authority
CN
China
Prior art keywords
layer
compound
organic
naphthalene
triaryl
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.)
Pending
Application number
CN201710055510.2A
Other languages
Chinese (zh)
Inventor
黄锦海
苏建华
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.)
Shanghai Taoe Chemical Technology Co Ltd
Original Assignee
Shanghai Taoe Chemical Technology Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shanghai Taoe Chemical Technology Co Ltd filed Critical Shanghai Taoe Chemical Technology Co Ltd
Priority to CN201710055510.2A priority Critical patent/CN106831313A/en
Publication of CN106831313A publication Critical patent/CN106831313A/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C07C15/24—Polycyclic condensed hydrocarbons containing two rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C07C15/27—Polycyclic condensed hydrocarbons containing three rings
    • C07C15/28—Anthracenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C07C15/38—Polycyclic condensed hydrocarbons containing four rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • 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
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08—Radicals containing only hydrogen and carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/107—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with two aryl or substituted aryl radicals attached in positions 2 and 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • 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
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—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
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H10K85/6565—Oxadiazole compounds
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—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
    • C09K2211/1059—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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/301—Details of OLEDs
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Abstract

The invention provides a kind of organic electroluminescent compounds with triaryl naphthalene, the compound has preferable heat endurance, high-luminous-efficiency, luminance purity high, can be used for making organic electroluminescence device, be applied to organic solar batteries, OTFT or organophotoreceptorswith field.Present invention also offers a kind of organic electroluminescence device, it includes anode, negative electrode and organic layer, organic layer includes at least one of which in luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, and at least one of which includes the compound just like structural formula I in organic layer.

Description

A kind of compound and its organic electroluminescence device with triaryl naphthalene
Technical field
The present invention relates to field of organic electroluminescent materials, and in particular to a kind of organic electroluminescent with triaryl naphthalene Compound and its organic electroluminescence device, belong to organic electroluminescence device display technology field.
Background technology
Organic electroluminescence device (OLEDs) is to deposit one by spin coating or vacuum evaporation between two metal electrodes The device that layer organic material is prepared from, the three of classics layers of organic electroluminescence device include hole transmission layer, luminescent layer And electron transfer layer.The hole produced by anode through hole transmission layer with the electronics that is produced by negative electrode through combined with electron transfer layer Luminescent layer forms exciton, then lights.Organic electroluminescence device can be adjusted as desired by the material for changing luminescent layer The light of the various needs of section transmitting.
Organic electroluminescence device as a kind of new Display Technique, with self-luminous, wide viewing angle, low energy consumption, efficiency High, thin, rich color, fast response time, Applicable temperature scope are wide, low driving voltage, can make flexible with it is transparent Display panel and the particular advantages such as environment-friendly, can apply on flat-panel monitor and a new generation's illumination, it is also possible to as The backlight of LCD.
Since invention at the bottom of the eighties in 20th century, organic electroluminescence device has industrially been applied, such as Used as screens such as camera and mobile phones, but current OLED is low due to efficiency, and it is wider that the factor such as service life is short restricts it General application, particularly large screen display, it is therefore desirable to improve the efficiency of device.And restrict one of key factor just It is the performance of the electroluminescent organic material in organic electroluminescence device.Run in applied voltage additionally, due to OLED When, Joule heat can be produced so that organic material is susceptible to crystallization, have impact on life-span and the efficiency of device, therefore, it is also desirable to Develop the electroluminescent organic material of stability and high efficiency.
In organic electroluminescence device, the introducing of hole mobile material and injection material can be effectively reduced positive electricity Lotus is transferred to the ability of luminescent layer from positive pole, improves the efficiency of device and thermally-stabilised.Traditional hole-injecting material, such as copper Phthalocyanine (CuPc), degraded is slow, prepares power consumption height, is unfavorable for environmental protection, and it can absorb light, influence device Efficiency.NPB etc. original hole mobile material, heat endurance is poor, also largely influences device lifetime.Thus, need Develop the electroluminescent organic material of efficient stable.
In the middle of three primary colors (red, indigo plant, green), feux rouges and green light material have been achieved for very big development recently, also comply with The market demand of panel.For stable and efficient blue light material or seldom, due to the energy gap high of blue light so that for material Requirement it is higher, and the problem that stability due to blue phosphor materials and optical purity are present, thus exploitation efficient stable indigo plant Color fluorescent material is particularly important.
The content of the invention
Present invention firstly provides a kind of organic electroluminescent compounds with triaryl naphthalene, it is with following structural formula The compound of I：
Wherein, R1-R4Separately it is selected from hydrogen, deuterium, halogen, cyano group, nitro, C1-C8 alkyl, C1-C8 alkoxyl, C6- The substitution of C30 or unsubstituted aryl, the substitution of C3-C30 or the unsubstituted hetero atom virtue containing one or more Base；Ar1-Ar3Separately selected from the substitution or unsubstituted aryl, the substitution of C3-C30 or unsubstituted of C6-C30 Hetero atom aryl containing one or more；L is selected from phenyl and xenyl.
Preferably, R1-R4Separately it is selected from hydrogen, deuterium, fluorine, methyl, phenyl, pyridine radicals.
Preferably, Ar1And Ar2Separately it is selected from phenyl, naphthyl, xenyl, pyridine radicals.
Preferably, Ar3Selected from alkyl-substituted carbazyl, the anthracene of phenyl, naphthyl, N- aryl (C6-C30) or C1-C4 Base, phenanthryl, pyrenyl, perylenes base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (substitutions of 9,9- bis- or unsubstituted aryl) fluorenyl, 9, 9- is Spirofluorene-based, three fragrant (C6-C60) amidos, dibenzothiophenes base, dibenzofuran group, pyridine radicals, pyrimidine radicals, pyridazinyl, three Piperazine base, imidazole radicals, oxazolyls, thiazolyl, thiadiazolyl group, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, azepine hexichol And furan base, azepine dibenzothiophenes base, benzimidazolyl, benzothiazolyl, benzoxazolyl, quinolyl, quinoxalinyl, the above Aryl and heteroaryl can be replaced by the alkyl of C1-C12.
It is highly preferred that R1-R4Independently selected from hydrogen, deuterium；Ar1And Ar2It is phenyl.
It is further preferred that the organic electroluminescent compounds with triaryl naphthalene of the invention are following structural 1-82 Compound：
A kind of organic electroluminescent compounds with triaryl naphthalene structure of the invention can be applied to be sent out in organic electroluminescence Optical device, organic solar batteries, OTFT or organophotoreceptorswith field.
Present invention also offers a kind of organic electroluminescence device, the device includes anode, negative electrode and organic layer, organic layer In comprising luminescent layer, hole injection layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer at least one Layer, wherein at least one layer organic electroluminescent compounds contained as described in structural formula I in the organic layer：
Wherein R1-R4、Ar1-Ar3It is defined as described above with L.
Wherein organic layer is luminescent layer；
Or organic layer is luminescent layer and electron transfer layer；
Or organic layer is luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole transmission layer and luminescent layer；
Or organic layer is hole injection layer, hole transmission layer and luminescent layer；
Or organic layer is hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer and electron transfer layer；
Or organic layer is hole injection layer, hole transmission layer, luminescent layer, electron transfer layer and electron injecting layer；
Or organic layer is hole injection layer, hole transmission layer, barrier layer, luminescent layer, electron transfer layer and electron injection Layer；
Or organic layer is hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and hole blocking layer；
Or organic layer is hole transmission layer, luminescent layer, electron injecting layer and hole blocking layer.
Preferably, wherein the layer where compound as described in structural formula I be luminescent layer, hole transmission layer, hole injection layer, Electron transfer layer, electron injecting layer.
Preferably, the compound wherein described in structural formula I is the compound of structural formula 1-82.
When the organic electroluminescent compounds with triaryl naphthalene as described in structural formula I are prepared for luminescent device, can To be used alone, it is also possible to and other compounds are used in mixed way；The hair of the organic electroluminescence with triaryl naphthalene as described in structural formula I Optical compounds can be used alone a kind of compound therein, it is also possible to while using the two or more chemical combination in structural formula I Thing.
Organic electroluminescence device of the invention, further preferred mode is that the organic electroluminescence device includes sun Contain in pole, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and negative electrode, wherein luminescent layer The compound of more than one structural formula I；It is further preferred that in luminescent layer the structural formula 1-82 containing more than one chemical combination Thing.
The luminescent layer of organic electroluminescence device contains light emitting guest material and the compound with structural formula I as main body , used as material of main part, its concentration is the 20-99.9% of entirely luminous layer weight, preferably 80- for material, wherein Compounds of structural formula I 99%, more preferably 90-99%.
The gross thickness of organic electroluminescence device organic layer of the invention is 1-1000nm, preferably 50-500nm.
When having the compound of structural formula I using the present invention, can arrange in pairs or groups makes organic electroluminescence device of the invention With other materials, such as in hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer and barrier layer Deng, and obtain blue and green light, gold-tinted, feux rouges or white light.
The hole transmission layer and hole injection layer of organic electroluminescence device of the present invention, material requested have good hole Transmission performance, can effectively be transferred to hole on luminescent layer from anode.Except the compound with I of the present invention can be used Outward, other small molecules and macromolecular organic compound, including but not limited to carbazole compound, triaromatic amine can also be included Compound, benzidine compound, compound of fluorene class, phthalocyanine-like compound, the miscellaneous triphen of six cyano group six (hexanitrilehexaazatriphenylene), the cyanogen dimethyl-parabenzoquinone (F4- of 2,3,5,6- tetra- fluoro- 7,7', 8,8'- tetra- TCNQ), PVK, polythiophene, polyethylene or polyphenyl sulfonic acid.
The luminescent layer of organic electroluminescence device of the invention, with the good characteristics of luminescence, can be adjusted as needed The scope of visible ray.Except it is of the invention with Compounds of structural formula I in addition to, can also contain following compound, but not limited to this, Naphthalene compounds, pyrene compound, compound of fluorene class, luxuriant and rich with fragrance class compound, class compound in the wrong, glimmering anthracene compound, anthracene class chemical combination Thing, pentacene class compound, perylene classes compound, two aromatic ethylene class compounds, triphenylamine ethylene compounds, aminated compounds, Benzimidazoles compound, furfuran compound, organic metal chelate complex.
The Organic Electron Transport Material requirement of organic electroluminescence device of the present invention has good electronic transmission performance, energy It is enough effectively electronics from cathode transport to luminescent layer in, with very big electron mobility.Except that can be of the inventionization Outside compound, it is also an option that following compound, but not limited to this：Oxa- oxazole, thiazole compound, triazole chemical combination Thing, three nitrogen piperazine class compounds, triazine class compound, quinoline class compound, phenodiazine anthracene compound, siliceous heterocyclic chemical combination Thing, quinolines, ferrosin class compound, metallo-chelate (such as Alq3), fluorine substituted benzene compound, benzimidazole Compound.
Electronics, effectively can be injected into organic layer by the electron injecting layer of organic electroluminescence device of the present invention from negative electrode In, the compound of alkali metal or alkali metal is mainly selected from, or selected from alkaline-earth metal or the compound or alkali of alkaline-earth metal Metal complex, can select following compound, but not limited to this：Alkali metal, alkaline-earth metal, rare earth metal, alkali metal Oxide or halide, the oxide of alkaline-earth metal or halide, the oxide of rare earth metal or halide, alkali metal Or the organic complex of alkaline-earth metal；Preferably lithium, lithium fluoride, lithia, lithium nitride, 8-hydroxyquinoline lithium, caesium, carbonic acid Caesium, 8-hydroxyquinoline caesium, calcium, calcirm-fluoride, calcium oxide, magnesium, magnesium fluoride, magnesium carbonate, magnesia, these compounds can individually make With can also mixture use, it is also possible to used cooperatively with other electroluminescent organic materials.
Each layer of organic layer in organic electroluminescence device of the invention, can be steamed by vacuum vapour deposition, molecular beam It is prepared by the modes such as plating method, the dip coating for being dissolved in solvent, spin-coating method, stick coating method or inkjet printing.Can make for metal motor It is prepared with vapour deposition method or sputtering method.
Device experimental shows that organic electroluminescent compounds with triaryl naphthalene of the present invention as described in structural formula I have There are preferable heat endurance, high-luminous-efficiency, luminance purity high.There is the organic electroluminescent compounds system of triaryl naphthalene using this The organic electroluminescence device of work has the advantages that electroluminescent efficiency is good and excitation is excellent and long lifespan.
Brief description of the drawings
Fig. 1 is a kind of organic electroluminescence device structural representation of the invention；
Wherein, 110 glass substrate is represented as, 120 are represented as anode, and 130 are represented as hole transmission layer, and 140 are represented as hair Photosphere, 150 are represented as electron transfer layer, and 160 are represented as electron injecting layer, and 170 are represented as negative electrode.
Specific embodiment
In order to describe the present invention in more detail, especially exemplified by example below, but not limited to this.
The synthesis of 2- (4- bromophenyls naphthalene) -1,4- diphenyl naphthalenes
In flask, add 1,3- diphenyl isobenzofuran (10g, 37mmol), to bromobenzene acetylene (6.7g, 37mmol) With mesitylene (100ml), it is heated to reflux under nitrogen protection 10 hours, cools down, remove solvent, crude product is purified through column chromatography Obtain 5.6g, yield 35%.
The synthesis of 2- (3- bromophenyls naphthalene) -1,4- diphenyl naphthalenes
Synthetic method as 2- (4- bromophenyls naphthalene)-Isosorbide-5-Nitrae-diphenyl naphthalene, except being replaced to bromobenzene with a bromobenzene acetylene Outside acetylene, yield 43%.
Embodiment 1
The synthesis of compound 4
In flask, 2- (4- bromophenyls naphthalene)-Isosorbide-5-Nitrae-diphenyl naphthalene (1.4g, 3.2mmol), 9- (1- naphthyls) -10- are added Anthracene boric acid (1.1g, 3.2mmol), potassium carbonate (0.9g, 6.5mmol), tetra-triphenylphosphine palladium (0.2g), tetrahydrofuran (20mL) and Water (10ml), is heated to reflux 10 hours under nitrogen protection, cooling, removes tetrahydrofuran, filtering, filter cake tetrahydrofuran and second Alcohol is recrystallized, and obtains 1.6g, yield 76%.
Embodiment 2
The synthesis of compound 5
Synthetic method with as compound 4, except replacing 9- (1- naphthyls) -10- anthracenes with 9- (2- naphthalenes) -10- anthracene boric acid Outside boric acid, yield 70%.
Embodiment 3
The synthesis of compound 17
Synthetic method as compound 5, except replacing 2- (4- bromobenzenes with 2- (3- bromophenyls)-Isosorbide-5-Nitrae-diphenyl naphthalene Base)-Isosorbide-5-Nitrae-diphenyl naphthalene replaces outer, yield 80%.
Embodiment 4
The synthesis of compound 29
In flask, 2- (4- bromophenyls naphthalene)-Isosorbide-5-Nitrae-diphenyl naphthalene (2g, 4.6mmol), N- [1,1 '-biphenyl -4- are added Base] -9,9- dimethyl -9H- fluorenes -2- amine (1.7g, 4.6mmol), sodium tert-butoxide (0.9g, 9.2mmol) and palladium The ortho-xylene of (0.15g), X-phos (0.3g) and 30ml, is heated to reflux 10 hours, cooling, removes solvent, and crude product is through post Chromatographic purifying obtains 2.1g, yield 63%.
Embodiment 5
The synthesis of compound 41
With as compound 29, raw material used is 2- (3- bromophenyls)-Isosorbide-5-Nitrae-diphenyl naphthalene and two (4- to synthetic method Biphenyl) amine, yield 55%.
Embodiment 6
The synthesis of compound 42
Synthetic method with as compound 41, it is raw materials used for 2- (3- bromophenyls)-Isosorbide-5-Nitrae-diphenyl naphthalene and N- [1, 1 '-biphenyl -4- bases] -9,9- dimethyl -9H- fluorenes -2- amine, yield 73%.
Embodiment 7
The synthesis of compound 56
The synthesis of intermediate 56-1
In flask, 2- (4- bromophenyls naphthalene)-Isosorbide-5-Nitrae-diphenyl naphthalene (5g, 11.5mmol), connection boric acid pinacol ester are added (3.5g, 14mmol), potassium acetate (2.25g, 23mmol), dichloro triphenylphosphine palladium (0.3g), dioxane (50ml), in nitrogen It is heated to reflux under protection 10 hours, is cooled down, remove solvent, add dichloromethane and water, point liquid is dried, concentration, crude product is through post layer Analysis purifying obtains 4.8g, yield 87%.
The synthesis of compound 56
In flask, add intermediate 56-1 (2g, 4.1mmol), chloro- 4, the 6- diphenyl -1,3,5-triazines of 2- (1.2g, 4.6mmol, potassium carbonate (1.1g, 8.2mmol), tetra-triphenylphosphine palladium (0.2g), tetrahydrofuran (30ml) and water (10ml), in nitrogen It is heated to reflux under gas shielded 10 hours, is cooled down, extracted with dichloromethane, dry concentration, crude product is obtained through column chromatography purifying 1.4g, yield 58%.
Embodiment 8
The synthesis of compound 68
Synthetic method with as compound 56, except with 2- (4- bromophenyls) -4,6- triazines replace chloro- 4, the 6- hexichol of 2- Outside base -1,3,5-triazines, yield 84%.
Embodiment 9
The synthesis of compound 70
Synthetic method as the synthesis of compound 56, except with 2- (3- bromophenyls) -4,6- triazines replace 2- chloro- 4,6- Outside diphenyl -1,3,5-triazines, yield 78%.
Embodiment 10
The synthesis of compound 73
The synthesis of intermediate 73-1
Synthetic method as intermediate 56-1, except replacing 2- (4- bromobenzenes with 2- (3- bromophenyls)-Isosorbide-5-Nitrae-diphenyl naphthalene Base) outside-Isosorbide-5-Nitrae-diphenyl naphthalene, yield 80%.
The synthesis of compound 73
Synthetic method with as compound 70, in addition to replacing intermediate 56-1 with intermediate 73-1, yield 91%.
Embodiment 11
The synthesis of compound 74
In flask, 2- (4- bromophenyls)-Isosorbide-5-Nitrae-diphenyl naphthalene (2.3g, 5.3mmol), B- [4- (1- phenyl -1H- are added Benzimidazolyl-2 radicals-yl) phenyl]-boric acid (1.8g, 5.8mmol), potassium carbonate (1.5g, 11mmol), tetra-triphenylphosphine palladium (0.2g), tetrahydrofuran (20ml) and water (10ml), are heated to reflux 10 hours under nitrogen protection, cooling, solvent are removed, with two Chloromethanes is extracted, and is dried, concentration, and crude product obtains 2.4g, yield 73% through column chromatography purifying.
Embodiment 12-14
The preparation of organic electroluminescence device
OLED is prepared using the compound of embodiment.
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (the South China glass group limited public affairs of share Department) pass through successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, compound N PB is deposited with, the thick hole transmission layers 130 of 60nm are formed.
Then, the thick luminescent layers 140 of 40nm are deposited with hole transmission layer.Wherein, the compounds of this invention and MADN distinguish Be main body luminescent material, and using 3% weight than BUBD-1 as doping guest materials.
Then, the thick Alq of 20nm are deposited with luminescent layer3As electron transfer layer 150.
Finally, evaporation 1nm LiF are electron injecting layer 160 and 100nm Al as device cathodes 170.
Prepared device (structure such as Fig. 1) is measured in 1000cd/m with Photo Research PR650 spectrometers2's Voltage under brightness is such as table 1 below.
Comparative example 1
In addition to luminescent layer replaces the compounds of this invention with MADN, others are as embodiment 8.Prepared device is used Photo Research PR650 spectrometers are measured in 1000cd/m2Brightness under voltage such as table 1 below.
Table 1 is in 1000cd/m2Voltage under brightness
Embodiment Compound Driving voltage (V) Spectrum
12 4 6 Blue light
13 5 5.8 Blue light
14 17 5.9 Blue light
Comparative example 1 MADN 6.5 Blue light
The organic electroluminescence device using compound of the invention preparation is can be seen that in identical brightness from upper result Under the conditions of, the driving voltage of device is less than comparative example.
The structural formula of compound described in device is as follows：
Embodiment 15-17
The preparation of organic electroluminescence device
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (the South China glass group limited public affairs of share Department) pass through successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, the compounds of this invention is deposited with, the thick hole transmission layers 130 of 60nm are formed.
Then, the thick compound Alq of 30nm are deposited with hole transmission layer3As luminescent layer 140.
Then, the thick Alq of 20nm are deposited with luminescent layer3As electron transfer layer 150.Finally, evaporation 1nmLiF is electricity Sub- implanted layer 160 and 100nm Al are used as device cathodes 170.
Prepared device (structure such as Fig. 1) is measured in 150mA/cm with Photo Research PR650 spectrometers2's Current efficiency under current density is such as table 2 below.
Comparative example 2
The preparation method of device in addition to replacing the compounds of this invention with compound N PB, is surveyed as embodiment 15-17 In 150mA/cm2Current density under current efficiency such as table 2.
Table 2 is in 150mA/cm2Current density under current efficiency
Embodiment Compound Current efficiency (cd/A) Spectrum
15 29 1.8 Green glow
16 41 1.9 Green glow
17 42 1.7 Green glow
Comparative example 2 NPB 1.2 Green glow
At identical conditions, the organic electroluminescence device for being prepared using organic electroluminescent compounds of the invention Current efficiency is higher than comparative example.As described above, compound of the invention has stability high, organic electroluminescence prepared by the present invention Luminescent device has low driving voltage, efficiency high and optical purity.
Embodiment 18-22
The preparation of organic electroluminescence device
OLED is prepared using compound of the invention.
First, by electrically conducting transparent ito glass substrate 110 (above with anode 120) (the South China glass group limited public affairs of share Department) pass through successively：Deionized water, ethanol, acetone and deionized water are cleaned, then with oxygen plasma treatment 30 seconds.
Then, NPB is deposited with, the thick hole transmission layers 130 of 60nm are formed.
Then, the thick Alq of 37.5nm are deposited with hole transmission layer31%C545T is used as luminescent layer 140 for doping.
Then, 37.5nm is deposited with luminescent layer thick as electron transfer layer 150, comprising 75% the compounds of this invention and 25% LiQ.
Finally, evaporation 1nm LiF are electron injecting layer 160 and 100nm Al as device cathodes 170.
Comparative example 3
Except electron transfer layer Alq3Outside instead of the compounds of this invention, others are as embodiment 18-22.
Prepared device (structural representation is shown in Fig. 1) is in 6000cd/m2Life-span such as table after being worked under brightness 24 hours 3。
Table 3 is in 6000cd/m2Life-span after being worked under brightness 24 hours
Embodiment Compound Life-span Color
18 56 81% Green glow
19 68 84% Green glow
20 70 85% Green glow
21 73 83% Green glow
22 74 82% Green glow
Comparative example 3 75% Green glow
At identical conditions, the organic electroluminescent for being prepared using organic electroluminescent electron transport material of the invention The life-span of device is higher than comparative example, as described above, compound of the invention has stability high, Organic Electricity prepared by the present invention Electroluminescence device has life-span and optical purity high.
Structural formula described in device
Preferred embodiment of the invention described in detail above.It should be appreciated that one of ordinary skill in the art without Need creative work just can make many modifications and variations with design of the invention.Therefore, all technologies in the art Personnel are available by logical analysis, reasoning, or a limited experiment on the basis of existing technology under this invention's idea Technical scheme, all should be in the protection domain being defined in the patent claims.

Claims (10)

1. a kind of organic electroluminescent compounds with triaryl naphthalene, it is characterised in that it is the change with following structural formula I Compound：
Wherein, R1-R4Separately it is selected from hydrogen, deuterium, halogen, cyano group, nitro, C1-C8 alkyl, C1-C8 alkoxyl, C6-C30 Substitution or unsubstituted aryl, the substitution of C3-C30 or the unsubstituted hetero atom aryl containing one or more； Ar1-Ar3Separately selected from C6-C30 substitution or unsubstituted aryl, the substitution of C3-C30 or it is unsubstituted containing One or more hetero atom aryl；L is selected from phenyl and xenyl.
2. organic electroluminescent compounds with triaryl naphthalene according to claim 1, it is characterised in that R1-R4Respectively Independently selected from hydrogen, deuterium, fluorine, methyl, phenyl, pyridine radicals, Ar1And Ar2Separately it is selected from phenyl, naphthyl, xenyl, pyrrole Piperidinyl.
3. organic electroluminescent compounds with triaryl naphthalene according to claim 1, it is characterised in that Ar3Selected from benzene The alkyl-substituted carbazyl of base, naphthyl, N- aryl (C6-C30) or C1-C4, anthryl, phenanthryl, pyrenyl, perylenes base, fluoranthene base, (9,9- dialkyl group) fluorenyl, (substitutions of 9,9- bis- or unsubstituted aryl) fluorenyl, 9,9- are Spirofluorene-based, three fragrant (C6-C60) amine Base, dibenzothiophenes base, dibenzofuran group, pyridine radicals, pyrimidine radicals, pyridazinyl, triazine radical, imidazole radicals, oxazolyls, thiazole Base, thiadiazolyl group, quinolyl, isoquinolyl, quinazolyl, quinoxalinyl, azepine dibenzo furan base, azepine dibenzothiophenes Base, benzimidazolyl, benzothiazolyl, benzoxazolyl, quinolyl, quinoxalinyl, or more aryl and heteroaryl by C1- The alkyl substitution of C12.
4. organic electroluminescent compounds with triaryl naphthalene according to claim 1, it is characterised in that R1-R4It is independent Ground is selected from hydrogen, deuterium；Ar1And Ar2It is phenyl.
5. organic electroluminescent compounds with triaryl naphthalene according to claim 1, it is characterised in that it is following The compound of structural formula 1-82：
6. a kind of organic electroluminescence device, it includes anode, negative electrode and organic layer, and organic layer injects comprising luminescent layer, hole At least one of which in layer, hole transmission layer, hole blocking layer, electron injecting layer, electron transfer layer, it is characterised in that described organic At least one layer contains the organic electroluminescent compounds with triaryl naphthalene as claimed in claim 1 in layer.
7. organic electroluminescence device according to claim 6, it is characterised in that as described in structural formula I with triaryl Layer where the organic electroluminescent compounds of naphthalene is luminescent layer, hole transmission layer, hole injection layer, electron transfer layer, electronics note Enter at least one of which in layer.
8. organic electroluminescence device according to claim 6, it is characterised in that as described in structural formula I with triaryl The organic electroluminescent compounds of naphthalene are the compound of structural formula 1-82.
9. organic electroluminescence device according to claim 6, it is characterised in that as described in structural formula I with triaryl The organic electroluminescent compounds of naphthalene are used alone, or are used in mixed way with other compounds.
10. organic electroluminescence device according to claim 6, it is characterised in that as described in structural formula I with three virtues The organic electroluminescent compounds of base naphthalene are used alone a kind of compound therein, or simultaneously using two kinds in structural formula I with On compound.
CN201710055510.2A 2017-01-25 2017-01-25 A kind of compound and its organic electroluminescence device with triaryl naphthalene Pending CN106831313A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201710055510.2A CN106831313A (en) 2017-01-25 2017-01-25 A kind of compound and its organic electroluminescence device with triaryl naphthalene

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201710055510.2A CN106831313A (en) 2017-01-25 2017-01-25 A kind of compound and its organic electroluminescence device with triaryl naphthalene

Publications (1)

Publication Number Publication Date
CN106831313A true CN106831313A (en) 2017-06-13

Family

ID=59120420

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201710055510.2A Pending CN106831313A (en) 2017-01-25 2017-01-25 A kind of compound and its organic electroluminescence device with triaryl naphthalene

Country Status (1)

Country Link
CN (1) CN106831313A (en)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107325104A (en) * 2017-08-07 2017-11-07 赵东敏 Hexaazaphenalene compound and application thereof
CN107325105A (en) * 2017-08-07 2017-11-07 赵东敏 A kind of that non-vinyl compound of six nitrogen and its application
CN107383029A (en) * 2017-08-07 2017-11-24 赵东敏 That non-vinyl compound of six nitrogen of one kind and its application
CN107516712A (en) * 2017-08-07 2017-12-26 赵东敏 Organic electroluminescence device containing that non-vinyl compound of six nitrogen
CN108084180A (en) * 2017-12-26 2018-05-29 南京高光半导体材料有限公司 A kind of novel electroluminescent compound and the organic electroluminescence device using the organic electroluminescent compounds
CN109206327A (en) * 2017-06-30 2019-01-15 东进世美肯株式会社 Compounds and organic luminescent device comprising it
CN109206324A (en) * 2017-07-07 2019-01-15 东进世美肯株式会社 Compounds and organic luminescent device comprising it
CN109749735A (en) * 2017-11-08 2019-05-14 Sfc株式会社 The naphthalene derivatives that amine replaces and the Organic Light Emitting Diode comprising it
WO2020252760A1 (en) * 2019-06-21 2020-12-24 复旦大学 Controllable long persistent luminescent material
KR20220070210A (en) 2019-09-26 2022-05-30 이데미쓰 고산 가부시키가이샤 Compounds, materials for organic electroluminescent devices, organic electroluminescent devices and electronic devices
KR20220081340A (en) 2019-10-11 2022-06-15 이데미쓰 고산 가부시키가이샤 Compounds, materials for organic electroluminescent devices, organic electroluminescent devices and electronic devices
US11417843B2 (en) 2018-10-12 2022-08-16 Samsung Display Co., Ltd. Organic electroluminescence device and amine compound for organic electroluminescence device
US11805697B2 (en) 2018-01-26 2023-10-31 Samsung Display Co., Ltd. Organic electroluminescence device and monoamine compound for organic electroluminescence device
US11849632B2 (en) 2019-03-20 2023-12-19 Samsung Display Co., Ltd. Amine-based compound and organic light-emitting device including the same
CN114989109B (en) * 2021-03-01 2024-01-05 武汉天马微电子有限公司 Compound, material for organic electroluminescent device and application thereof
US11871656B2 (en) 2018-01-26 2024-01-09 Samsung Display Co., Ltd. Organic electroluminescence device and monoamine compound for organic electroluminescence device
US11925108B2 (en) 2018-06-25 2024-03-05 Hodogaya Chemical Co., Ltd. Compound having triarylamine structure and organic electroluminescence device

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
HUGUET, NURIA等: "Intermolecular Gold(I)-Catalyzed Cyclization of Furans with Alkynes:Formation of Phenols and Indenes", 《CHEMISTRY - A EUROPEAN JOURNAL》 *
LAPORTE, MATTHEW等: "5-Hydroxyindoles by Intramolecular Alkynol-Furan Diels-Alder Cycloaddition", 《JOURNAL OF ORGANIC CHEMISTRY》 *

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109206327A (en) * 2017-06-30 2019-01-15 东进世美肯株式会社 Compounds and organic luminescent device comprising it
CN109206327B (en) * 2017-06-30 2024-03-08 东进世美肯株式会社 Novel compound and organic light emitting device comprising the same
CN109206324A (en) * 2017-07-07 2019-01-15 东进世美肯株式会社 Compounds and organic luminescent device comprising it
CN107325104B (en) * 2017-08-07 2019-05-24 深圳市鑫航盛科技有限公司 Hexaazaphenalene compound and application thereof
CN107516712A (en) * 2017-08-07 2017-12-26 赵东敏 Organic electroluminescence device containing that non-vinyl compound of six nitrogen
CN107383029A (en) * 2017-08-07 2017-11-24 赵东敏 That non-vinyl compound of six nitrogen of one kind and its application
CN107516712B (en) * 2017-08-07 2019-04-09 深圳市骏辉腾科技有限公司 Organic electroluminescence device containing that non-vinyl compound of six nitrogen
CN107325105B (en) * 2017-08-07 2019-04-23 深圳市国瑧科技有限公司 That non-vinyl compound of six nitrogen of one kind and its application
CN107325104A (en) * 2017-08-07 2017-11-07 赵东敏 Hexaazaphenalene compound and application thereof
CN107325105A (en) * 2017-08-07 2017-11-07 赵东敏 A kind of that non-vinyl compound of six nitrogen and its application
CN109749735A (en) * 2017-11-08 2019-05-14 Sfc株式会社 The naphthalene derivatives that amine replaces and the Organic Light Emitting Diode comprising it
CN108084180A (en) * 2017-12-26 2018-05-29 南京高光半导体材料有限公司 A kind of novel electroluminescent compound and the organic electroluminescence device using the organic electroluminescent compounds
US11805697B2 (en) 2018-01-26 2023-10-31 Samsung Display Co., Ltd. Organic electroluminescence device and monoamine compound for organic electroluminescence device
US11871656B2 (en) 2018-01-26 2024-01-09 Samsung Display Co., Ltd. Organic electroluminescence device and monoamine compound for organic electroluminescence device
US11925108B2 (en) 2018-06-25 2024-03-05 Hodogaya Chemical Co., Ltd. Compound having triarylamine structure and organic electroluminescence device
US11417843B2 (en) 2018-10-12 2022-08-16 Samsung Display Co., Ltd. Organic electroluminescence device and amine compound for organic electroluminescence device
US11849632B2 (en) 2019-03-20 2023-12-19 Samsung Display Co., Ltd. Amine-based compound and organic light-emitting device including the same
CN114040961A (en) * 2019-06-21 2022-02-11 复旦大学 Controllable long-afterglow luminescent material
WO2020252760A1 (en) * 2019-06-21 2020-12-24 复旦大学 Controllable long persistent luminescent material
KR20220070210A (en) 2019-09-26 2022-05-30 이데미쓰 고산 가부시키가이샤 Compounds, materials for organic electroluminescent devices, organic electroluminescent devices and electronic devices
KR20220081340A (en) 2019-10-11 2022-06-15 이데미쓰 고산 가부시키가이샤 Compounds, materials for organic electroluminescent devices, organic electroluminescent devices and electronic devices
CN114989109B (en) * 2021-03-01 2024-01-05 武汉天马微电子有限公司 Compound, material for organic electroluminescent device and application thereof

Similar Documents

Publication Publication Date Title
CN106831313A (en) A kind of compound and its organic electroluminescence device with triaryl naphthalene
CN105669467B (en) A kind of compound and its organic electroluminescence device based on fluoranthene
CN105175313B (en) A kind of hole injection compound and its organic electroluminescence device
CN105601612B (en) Phosphorescence host compound containing indolyl radical and its organic electroluminescence device
CN105294663B (en) One kind containing pyridine compounds and its organic electroluminescence device
CN106478566A (en) Organic electroluminescent compounds and its organic electroluminescence device based on dibenzofurans
CN109336772A (en) A kind of triaromatic amine compound containing spiro structure and application thereof and luminescent device
CN106518882A (en) Helical structural organic light emitting material and organic light emitting device thereof
CN108752221A (en) A kind of triaromatic amine compound containing fluorenes and application thereof and luminescent device
CN106883204A (en) Organic electroluminescent compounds and luminescent device based on benzo [b] naphtho- [1,2 d] furans
CN109535175A (en) A kind of double triaromatic amine compounds, application and the luminescent device of the spiro structure containing five-membered ring
CN107253954A (en) Compound and its organic electroluminescence device containing pyridine groups
CN107382992A (en) A kind of carbazoles organic electroluminescent compounds and its organic electroluminescence device
CN106543152A (en) Phosphorescence host compound and its organic luminescent device based on naphtho- benzofuran
CN107721979A (en) A kind of organic electroluminescent compounds and its organic electroluminescence device based on pyridine and triazine
CN107417677A (en) A kind of carbazole pyridines organic electroluminescent compounds and its organic electroluminescence device
CN108658953A (en) A kind of compound based on dibenzofurans and carbazole and application thereof and luminescent device
CN106632360A (en) Compound based on benzofuroindole and organic electroluminescent device thereof
CN106632325A (en) Azacycle-containing compound and organic electroluminescence device thereof
CN106831798B (en) Compound and its organic electroluminescence device containing five-membered ring structure
CN107641126A (en) A kind of organic electroluminescent compounds based on Imidazopyridazine and application thereof and organic electroluminescence device
CN106892903A (en) Organic electroluminescent compounds and its luminescent device based on phenol piperazine and carbazole
CN106749234A (en) Organic electroluminescent electron transport compound and its luminescent device based on anthracene
CN108658789A (en) A kind of triaromatic amine compound containing fluorenes and application thereof and luminescent device
CN106749289B (en) A kind of organic electroluminescent compounds and its luminescent device with spiro structure

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
WD01 Invention patent application deemed withdrawn after publication
WD01 Invention patent application deemed withdrawn after publication

Application publication date: 20170613