CN109180560A - 一种有机发光化合物及制法和含该化合物的有机电致发光器件 - Google Patents

一种有机发光化合物及制法和含该化合物的有机电致发光器件 Download PDF

Info

Publication number
CN109180560A
CN109180560A CN201811180929.1A CN201811180929A CN109180560A CN 109180560 A CN109180560 A CN 109180560A CN 201811180929 A CN201811180929 A CN 201811180929A CN 109180560 A CN109180560 A CN 109180560A
Authority
CN
China
Prior art keywords
unsubstituted
substituted
compound
organic
layer
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
CN201811180929.1A
Other languages
English (en)
Inventor
汪康
王辉
马晓宇
张成成
孙毅
金成寿
李文军
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.)
Jilin Optical and Electronic Materials Co Ltd
Original Assignee
Jilin Optical and Electronic Materials 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 Jilin Optical and Electronic Materials Co Ltd filed Critical Jilin Optical and Electronic Materials Co Ltd
Priority to CN201811180929.1A priority Critical patent/CN109180560A/zh
Publication of CN109180560A publication Critical patent/CN109180560A/zh
Priority to PCT/CN2019/078284 priority patent/WO2020073605A1/zh
Pending legal-status Critical Current

Links

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
    • 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
    • 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
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • 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
    • C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
    • 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
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
    • 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
    • C07D271/12—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • 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
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/14—Thiadiazoles; Hydrogenated thiadiazoles condensed with carbocyclic rings or ring systems
    • 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
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/58—Radicals substituted by nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—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
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—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 Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
    • C07F7/0807—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms comprising Si as a ring atom
    • 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 Table
    • C07F7/30—Germanium compounds
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—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
    • C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—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
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms

Landscapes

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

Abstract

本发明涉及有机发光材料技术领域，具体涉及一种有机发光化合物及制法和含该化合物的有机电致发光器件。本发明提供的有机发光化合物通过引入芳基胺获得了空穴注入能力/传输能力，高功率效率、长寿命；通过引入杂环获得适当玻璃态转变温度，从而获得了优质的有机电致发光材料。由本发明的机发光化合物制备的有机电致发光器件具有极佳电流效率和功率效率以及长寿命。本发明的有机发光化合物的制备方法，重复性好，产率高。

Description

一种有机发光化合物及制法和含该化合物的有机电致发光 器件
技术领域
本发明涉及有机发光材料技术领域，具体涉及一种有机发光化合物及制法和含该化合物的有机电致发光器件。
背景技术
电致发光装置(EL装置)为自动发光装置，其优点在于其可提供较宽的视角、较大的对比率和较快的响应时间。
有机EL元件是利用了如下原理的自发光元件：通过施加电场，利用由阳极注入的空穴与由阴极注入的电子的复合能使荧光性物质发光。它具有如下结构:阳极、阴极以及介于两者之间的有机物层。为了提高有机EL元件的效率和稳定性，有机材料层包括具有不同材料的多层，例如空穴注入层(HIL)、空穴传输层(HTL)、发光层、电子传输层(ETL)和电子注入层(EIL)。
在这种有机发光二极管中，当在阳极和阴极之间施加电压时，来自阳极的空穴和来自阴极的电子注入有机材料层。产生的激子在迁移至基态时产生具有特定波长的光。
决定有机EL装置中的发光效率的最重要因素是发光材料。到目前为止，荧光材料已经广泛用作发光材料。然而，鉴于电致发光机制，由于磷光材料在理论上与荧光材料相比使发光效率增强四倍，因此磷光发光材料的开发得到广泛研究。铱(III)络合物已广泛地被称为磷光掺杂材料。目前，4,4′-N,N′-二咔唑-联苯(CBP)、9,10-二(2-萘基)蒽(ADN)等作为已知的磷光主体材料得到广泛的应用。尽管这些材料提供良好发光特征，但其具有以下缺点：(1)由于其较低玻璃态转变温度和不良热稳定性，导致装置的寿命降低。(2)包含磷光主体材料的有机EL装置需要较高的驱动电压。同时，为了提高有机EL装置的效率和稳定性，需要其具有包含空穴注入层、空穴传输层、发光层、电子传输层和电子注入层的多层结构。其中空穴传输层可改变空穴到发光层的空穴传输效率、发光效率、寿命等。因此，使用铜酞菁(CuPc)、4,4′-双[N-(1-萘基)-N-苯基氨基]联苯(NPB)、N,N′-二苯基-N,N′-双(3-甲基苯基)-(1,1′-联苯)-4,4′-二胺(TPD)等作为空穴传输材料。然而，使用这些材料的有机EL装置在量子效率和使用寿命方面有问题。
发明内容
本发明要解决现有技术中的技术问题，提供一种有机发光化合物及制法和含该化合物的有机电致发光器件，由本发明的化合物制备的有机电致发光器件具有极佳电流效率和功率效率以及长寿命。
为了解决上述技术问题，本发明的技术方案具体如下：
本发明提供一种有机发光化合物，其结构式如下：
式中：Ar1和Ar2各自独立地表示经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3-30元杂芳基；或与相邻取代基连接形成单环或C3-C30多环脂环族环或芳香族环，其碳原子还可置换为至少一个选自氮、氧和硫的杂原子；
L表示苯基；
G环表示经取代或未经取代的C3-C30环烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3-30元杂芳基；
G环可以存在也可以不存在；
当G环不存在时X、Y、Z表示-O-、-S-、-SO2-、-C(R5)(R6)-、-N(R7)-、-Si-、-Sn-或者-Ge-；
当G环存在时X表示-SO2-、-N(R7)-、-Si-、-Sn-或者-Ge-；Y、Z表示C原子；
R1到R4各自独立地表示氢、氘、卤素、氰基、羧基、硝基、羟基、经取代或未经取代的C1-C30烃基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C3-C30环烯基、经取代或未经取代的3-7元杂环烷基、经取代或未经取代的C6-C30芳基、经取代或未经取代的3-30元杂芳基、-NR8R9、-SiR10R11R12、-SR13、-OR14、-COR15或者-B(OR16)(OR17)；或与相邻取代基连接形成经取代或未经取代的单环或C3-C30多环脂肪族环或芳香族环，其碳原子还可置换成至少一个选自氮、氧和硫的杂原子；
R5到R17各自独立地表示氢、经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3到30元杂芳基；或与相邻取代基连接形成经取代或未经取代的单环或C3-C30多环脂肪族环或芳香族环；
a、b和d各自独立地表示整数1到4；
c表示整数1到3。
在上述技术方案中，Ar1和Ar2各自独立地表示经取代或未经取代的C10-C25芳基，13-25元杂芳基。
在上述技术方案中，Ar1和Ar2各自独立地表示经取代或未经取代的C14-C21芳基，17-23元杂芳基。
在上述技术方案中，Ar1和Ar2各自独立地表示经取代或未经取代的C16-C19芳基，19-21元杂芳基。
在上述技术方案中，所述有机发光化合物选自下述结构中的任意一个：
本发明还提供一种有机发光化合物的制法，包括以下步骤：
步骤1、将化合物2加入到THF中溶解，在氮气气氛下将反应液冷却到-78℃，接着加入n-BuLi，在-78℃搅拌混合物至均匀，再在室温下搅拌，再冷却-78℃；将化合物1加入到THF中溶解，并将该混合溶液加入到前述化合物2的混合溶液中，并将温度升至室温后继续进行搅拌反应，接着将氯化铵水溶液添加到反应溶液中以完成反应，并且用乙酸乙酯萃取反应溶液，接着再使用硫酸镁干燥经萃取的有机物层，并且使用旋转式蒸发器去除溶剂，用管柱色谱法纯化剩余物质获得中间体1；
步骤2、将中间体1、化合物3和二氯甲烷加入到反应容器中之后，用氮气充分置换空气三次；将溶解于二氯甲烷中的三氟化硼乙醚逐滴添加到混合物中；在室温下进行搅拌反应，反应结束后用蒸馏水淬灭，并且用二氯甲烷萃取混合物；接着使用硫酸钠干燥萃取的有机物层，并且使用旋转式蒸发器去除溶剂，用柱色谱法纯化剩余物质获得式1化合物；
其合成路线如下：
其中：Ar1和Ar2各自独立地表示经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3-30元杂芳基；或与相邻取代基连接形成单环或C3-C30多环脂环族环或芳香族环，其碳原子还可置换为至少一个选自氮、氧和硫的杂原子；L表示苯基；G环表示经取代或未经取代的C3-C30环烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3-30元杂芳基；G环可以存在也可以不存在；当G环不存在时X、Y、Z表示-O-、-S-、-SO2-、-C(R5)(R6)-、-N(R7)-、-Si-、-Sn-或者-Ge-；当G环存在时X表示-SO2-、-N(R7)-、-Si-、-Sn-或者-Ge-；Y、Z表示C原子；R1到R4各自独立地表示氢、氘、卤素、氰基、羧基、硝基、羟基、经取代或未经取代的C1-C30烃基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C3-C30环烯基、经取代或未经取代的3-7元杂环烷基、经取代或未经取代的C6-C30芳基、经取代或未经取代的3-30元杂芳基、-NR8R9、-SiR10R11R12、-SR13、-OR14、-COR15或者-B(OR16)(OR17)；或与相邻取代基连接形成经取代或未经取代的单环或C3-C30多环脂肪族环或芳香族环，其碳原子还可置换成至少一个选自氮、氧和硫的杂原子；R5到R17各自独立地表示氢、经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3到30元杂芳基；或与相邻取代基连接形成经取代或未经取代的单环或C3-C30多环脂肪族环或芳香族环；a、b和d各自独立地表示整数1到4；c表示整数1到3，Hal为卤素。
本发明还提供一种含有上述有机发光化合物的有机电致发光器件。
在上述技术方案中，所述有机电致发光器件包括：
第一电极、第二电极和置于所述两电极之间的有机物层，其中，所述有机物层中包含有式1所示结构的化合物；式1所示结构的化合物可以是单一形态或与其它物质混合存在于有机物层中。
在上述技术方案中，所述有机物层至少包括空穴注入层，空穴传输层，既具备空穴注入又具备空穴传输技能层，电子阻挡层，发光层，空穴阻挡层，电子传输层，电子注入层和既具备电子传输又具备电子注入技能层中的一种或几种。
本发明中“有机物层”指的是有机电致发光器件第一电极和第二电极之间部署的全部层的术语。
当式1结构的化合物存在于所述有机物层中的发光层时，所述式1结构的化合物可以作为发光主体或者掺杂在其它荧光主体中；
当式1结构的化合物存在于所述有机物层中的空穴传输层或者空穴注入层时，所述式1结构的化合物可以作为空穴传输层、空穴注入层以及既具备空穴注入又具备空穴传输功能层。
本发明所述的包含有式1结构的化合物制备的器件可以用于有机发光器件(OLED)、有机太阳电池(OSC)、电子纸(e-Paper)、有机感光体(OPC)或有机薄膜晶体管(OTFT)。
本发明所述的有机电致发光器件可以通过薄膜蒸镀、电子束蒸发、物理气相沉积等方法在基板上蒸镀金属以及具有导电性的氧化物及他们的合金形成阳极，也可以采用旋转涂膜(spin-coating)或薄带带头蒸镀；还可以采用成型(tape-casting)、刮片法(doctor-blading)、丝网印刷(Screen-Printing)、喷墨印刷或热成像(Thermal-Imaging)等方法减少层数制造。
本发明的有益效果是：
本发明提供用于有机EL装置中的可解决传统技术问题的空穴传输材料。传统的空穴传输材料基本以三芳基衍生物为主。虽然其具有空穴传输能力和低驱动电压，但是为了获得合适的玻璃态转变温度而不得不在其结构上引入大量的取代基提升其分子量。但是这样却降低三重态能量或LUMO能量，从而导致有机电致发光器件的劣化。理想的空穴传输材料需要高玻璃态转变温度、空穴注入能力和空穴传输能力，以及适合三重态能量和LUMO能量。因此，为了解决传统空穴传输材料中存在的问题而得到理想的材料，本发明提出向芴的9-位引入芳基胺和杂环的解决方案。通过引入芳基胺获得了空穴注入能力/传输能力，高功率效率、长寿命；通过引入杂环获得适当玻璃态转变温度，从而获得了优质的有机电致发光材料。
由本发明的有机发光化合物制备的有机电致发光器件具有极佳电流效率和功率效率以及长寿命。
本发明的有机发光化合物的制备方法，重复性好，产率高。
具体实施方式
本发明将通过具体的实施例对本发明进行详细描述。然而，以下描述旨在解释本发明，并且不打算以任何方式限制本发明的范围。
本发明提供一种有机发光化合物，其结构式如下：
式中：Ar1和Ar2各自独立地表示经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3-30元杂芳基；或与相邻取代基连接形成单环或C3-C30多环脂环族环或芳香族环，其碳原子还可置换为至少一个选自氮、氧和硫的杂原子；
L表示苯基；
G环表示经取代或未经取代的C3-C30环烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3-30元杂芳基；
G环可以存在也可以不存在；
当G环不存在时X、Y、Z表示-O-、-S-、-SO2-、-C(R5)(R6)-、-N(R7)-、-Si-、-Sn-或者-Ge-；
当G环存在时X表示-SO2-、-N(R7)-、-Si-、-Sn-或者-Ge-；Y、Z表示C原子；
R1到R4各自独立地表示氢、氘、卤素、氰基、羧基、硝基、羟基、经取代或未经取代的C1-C30烃基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C3-C30环烯基、经取代或未经取代的3-7元杂环烷基、经取代或未经取代的C6-C30芳基、经取代或未经取代的3-30元杂芳基、-NR8R9、-SiR10R11R12、-SR13、-OR14、-COR15或者-B(OR16)(OR17)；或与相邻取代基连接形成经取代或未经取代的单环或C3-C30多环脂肪族环或芳香族环，其碳原子还可置换成至少一个选自氮、氧和硫的杂原子；
R5到R17各自独立地表示氢、经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3到30元杂芳基；或与相邻取代基连接形成经取代或未经取代的单环或C3-C30多环脂肪族环或芳香族环；
a、b和d各自独立地表示整数1到4；
c表示整数1到3。
优选，Ar1和Ar2各自独立地表示经取代或未经取代的C10-C25芳基，13-25元杂芳基。再优选，Ar1和Ar2各自独立地表示经取代或未经取代的C14-C21芳基，17-23元杂芳基。进一步优选，Ar1和Ar2各自独立地表示经取代或未经取代的C16-C19芳基，19-21元杂芳基。
最优选所述有机发光化合物选自下述结构中的任意一个：
本发明还提供一种有机发光化合物的制法，包括以下步骤：
步骤1、将化合物2加入到THF中溶解，在氮气气氛下将反应液冷却到-78℃，接着加入n-BuLi，在-78℃搅拌混合物至均匀，再在室温下搅拌，再冷却-78℃；将化合物1加入到THF中溶解，并将该混合溶液加入到前述化合物2的混合溶液中，并将温度升至室温后继续进行搅拌反应，接着将氯化铵水溶液添加到反应溶液中以完成反应，并且用乙酸乙酯萃取反应溶液，接着再使用硫酸镁干燥经萃取的有机物层，并且使用旋转式蒸发器去除溶剂，用管柱色谱法纯化剩余物质获得中间体1；
步骤2、将中间体1、化合物3和二氯甲烷加入到反应容器中之后，用氮气充分置换空气三次；将溶解于二氯甲烷中的三氟化硼乙醚逐滴添加到混合物中；在室温下进行搅拌反应，反应结束后用蒸馏水淬灭，并且用二氯甲烷萃取混合物；接着使用硫酸钠干燥萃取的有机物层，并且使用旋转式蒸发器去除溶剂，用柱色谱法纯化剩余物质获得式1化合物；
其合成路线如下：
其中：Ar1和Ar2各自独立地表示经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3-30元杂芳基；或与相邻取代基连接形成单环或C3-C30多环脂环族环或芳香族环，其碳原子还可置换为至少一个选自氮、氧和硫的杂原子；L表示苯基；G环表示经取代或未经取代的C3-C30环烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3-30元杂芳基；G环可以存在也可以不存在；当G环不存在时X、Y、Z表示-O-、-S-、-SO2-、-C(R5)(R6)-、-N(R7)-、-Si-、-Sn-或者-Ge-；当G环存在时X表示-SO2-、-N(R7)-、-Si-、-Sn-或者-Ge-；Y、Z表示C原子；R1到R4各自独立地表示氢、氘、卤素、氰基、羧基、硝基、羟基、经取代或未经取代的C1-C30烃基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C3-C30环烯基、经取代或未经取代的3-7元杂环烷基、经取代或未经取代的C6-C30芳基、经取代或未经取代的3-30元杂芳基、-NR8R9、-SiR10R11R12、-SR13、-OR14、-COR15或者-B(OR16)(OR17)；或与相邻取代基连接形成经取代或未经取代的单环或C3-C30多环脂肪族环或芳香族环，其碳原子还可置换成至少一个选自氮、氧和硫的杂原子；R5到R17各自独立地表示氢、经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3到30元杂芳基；或与相邻取代基连接形成经取代或未经取代的单环或C3-C30多环脂肪族环或芳香族环；a、b和d各自独立地表示整数1到4；c表示整数1到3，Hal为卤素。
在发光层和空穴传输层中的至少一个中可以包含根据本发明的有机电致发光化合物。
本发明还提供一种含有上述有机发光化合物的有机电致发光器件。
优选所述有机电致发光器件包括：第一电极、第二电极和置于所述两电极之间的有机物层，其中，所述有机物层中包含至少一种式1的所示结构的化合物；式1所示结构的化合物可以是单一形态或与其它物质混合存在于有机物层中。
所述第一和第二电极中的一个是阳极，且另一个是阴极。所述有机物层包含发光层，并且进一步包含至少一个选自空穴注入层、空穴传输层、电子传输层、电子注入层、、空穴阻挡层以及电子阻挡层组成的群组的层。
优选所述有机物层至少包括空穴注入层，空穴传输层，既具备空穴注入又具备空穴传输技能层，电子阻挡层，发光层，空穴阻挡层，电子传输层，电子注入层和既具备电子传输又具备电子注入技能层中的一种或几种。
本发明中“有机物层”指的是有机电致发光器件第一电极和第二电极之间部署的全部层的术语。
当式1结构的化合物存在于所述有机物层中的发光层时，所述式1结构的化合物可以作为发光主体或者掺杂在其它荧光主体中；
当式1结构的化合物存在于所述有机物层中的空穴传输层或者空穴注入层时，所述式1结构的化合物可以作为空穴传输层、空穴注入层以及既具备空穴注入又具备空穴传输功能层。
本发明所述的包含有式1结构的化合物制备的器件可以用于有机发光器件(OLED)、有机太阳电池(OSC)、电子纸(e-Paper)、有机感光体(OPC)或有机薄膜晶体管(OTFT)。
本发明所述的有机电致发光器件可以通过薄膜蒸镀、电子束蒸发、物理气相沉积等方法在基板上蒸镀金属以及具有导电性的氧化物及他们的合金形成阳极，也可以采用旋转涂膜(spin-coating)或薄带带头蒸镀；还可以采用成型(tape-casting)、刮片法(doctor-blading)、丝网印刷(Screen-Printing)、喷墨印刷或热成像(Thermal-Imaging)等方法减少层数制造。
本发明涉及式1的有机发光化合物及其制备方法，包含所述化合物的有机电致发光器件。
实施例1：制备化合物1
在反应容器中加入4-溴-9-苯基咔唑(60mmol)和200mL四氢呋喃之后，在氮气气氛下使所述容器冷却到-78℃。接着将正丁基锂(2.5M，60mmol)缓慢逐滴添加到混合物中。在-78℃下搅拌混合物30分钟后，将其在室温下搅拌3小时，并且冷却到-78℃。此后，将溶解于200mL四氢呋喃中的芴酮(60mmol)缓慢逐滴添加到混合物中。添加后，使反应温度缓慢升温到室温，并且搅拌混合物16小时。接着将氯化铵水溶液添加到反应溶液中以完成反应，并且用乙酸乙酯萃取反应溶液。接着使用硫酸镁干燥经萃取的有机物层，并且使用旋转式蒸发器去除溶剂。用管柱色谱法纯化剩余物质获得化合物1-1(19.04g，75％质谱值:423.42)。
将化合物1-1(45mmol)、化合物2-1三苯基胺(46mmol)和500L二氯甲烷加入反应容器中之后，用氮气充分置换空气三次。将溶解于100mL二氯甲烷中的三氟化硼乙醚(46mmol)缓慢逐滴添加到混合物中。在室温下搅拌混合物2小时后，用蒸馏水淬灭，并且用二氯甲烷萃取混合物。接着使用硫酸钠干燥萃取的有机物层，并且使用旋转式蒸发器去除溶剂。用柱色谱法纯化剩余物质获得化合物1(27.2g，93％,质谱值:650.22)。
实施例2：制备化合物7
按照实施例1的方法制备化合物7(产率＝75％质谱值:818.0)。与实施例1的不同之处在于使用中间体1-2代替中间体1-1，使用中间体2-7代替中间体2-1。
实施例3：制备化合物13
按照实施例2的方法制备化合物13(产率＝78％质谱值:776.15.0)。与实施例2的不同之处在于使用中间体2-13代替中间体2-7。
实施例4：制备化合物17
按照实施例2的方法制备化合物17(产率＝83％质谱值:843.02)。与实施例2的不同之处在于使用中间体2-17代替中间体2-7。
实施例5：制备化合物18
按照实施例2的方法制备化合物18(产率＝79％质谱值:858.33)。与实施例2的不同之处在于使用中间体2-18代替中间体2-7。
实施例6：制备化合物20
按照实施例2的方法制备化合物20(产率＝85％质谱值:884.40.)。与实施例2的不同之处在于使用中间体2-20代替中间体2-7。
实施例7：制备化合物28
按照实施例2的方法制备化合物28(产率＝86％质谱值:815.54)。与实施例2的不同之处在于使用中间体2-28代替中间体2-7。
实施例8：制备化合物31
按照实施例2的方法制备化合物31(产率＝77％质谱值:980.02)。与实施例2的不同之处在于使用中间体2-31代替中间体2-7。
实施例9：制备化合物35
按照实施例2的方法制备化合物35(产率＝81％质谱值:921.23)。与实施例2的不同之处在于使用中间体2-35代替中间体2-7。
实施例10：制备化合物40
按照实施例2的方法制备化合物40(产率＝82％质谱值:982.04)。与实施例2的不同之处在于使用中间体2-40代替中间体2-7。
实施例11：制备化合物41
按照实施例2的方法制备化合物41(产率＝87％质谱值:651.39)。与实施例2的不同之处在于使用中间体2-41代替中间体2-7。
实施例12：制备化合物42
按照实施例2的方法制备化合物42(产率＝79％质谱值:855.01)。与实施例2的不同之处在于使用中间体2-42代替中间体2-7。
实施例13：制备化合物45
按照实施例2的方法制备化合物45(产率＝86％质谱值:906.40)。与实施例2的不同之处在于使用中间体2-45代替中间体2-7。
实施例14：制备化合物46
按照实施例1的方法制备化合物46(产率＝85％质谱值:700.32)。与实施例1的不同之处在于使用中间体1-46代替中间体1-1。
实施例15：制备化合物51
按照实施例1的方法制备化合物51(产率＝88％质谱值:891.45)。与实施例1的不同之处在于使用中间体1-51代替中间体1-1。
实施例16：制备化合物54
按照实施例1的方法制备化合物54(产率＝83％质谱值:740.57)。与实施例1的不同之处在于使用中间体1-54代替中间体1-1。
实施例17：制备化合物61
按照实施例1的方法制备化合物61(产率＝84％质谱值:804.06)。与实施例1的不同之处在于使用中间体1-61代替中间体1-1，使用中间体2-61代替2-1。
实施例18：制备化合物77
按照实施例1的方法制备化合物77(产率＝85％质谱值:829.64)。与实施例1的不同之处在于使用中间体1-77代替中间体1-1，使用中间体2-77代替2-1。
实施例19：制造含有化合物1的有机电致发光器件
将涂层厚度为的ITO玻璃基板放在蒸馏水中清洗2次，超声波洗涤30分钟，用蒸馏水反复清洗2次，超声波洗涤10分钟，蒸馏水清洗结束后，异丙醇、丙酮、甲醇等溶剂按顺序超声波洗涤以后干燥，转移到等离子体清洗机里，将上述基板洗涤5分钟，送到蒸镀机里。将已经准备好的ITO透明电极上蒸镀厚度为50nm的4,4',4”-三[2-萘基苯基氨基]三苯基胺(2-TNATA)作为空穴注入层。然后将化合物1在形成的空穴注入层上面真空蒸镀厚度为30nm的空穴传输层。然后在上述空穴传输层上蒸镀厚度为30nm的蓝色主体材料9,10-二(2-萘基)蒽(ADN)和掺杂材料双(4,6-二氟苯基吡啶-N,C2)吡啶甲酰合铱(FIrpic)。主体材料和掺杂材料的重量比为95:5。接着在上述发光层上真空蒸镀厚度为40nm的TPBi作为空穴阻挡层及电子传输层。在上述电子传输层上真空蒸镀厚度为0.5nm氟化锂(LiF)，作为电子注入层。最后蒸镀厚度为150nm的铝作为阴极，以此完成了有机电致发光器件的制备。对得到的器件的性能发光特性测试，测量采用KEITHLEY 2400型源测量单元，CS-2000分光辐射亮度计，以评价驱动电压，发光亮度，发光效率。
实施例20：制造含有化合物7的有机电致发光器件
将实施例19中的化合物1置换为化合物7，其他方法相同，制作含有化合物7的有机电致发光器件。
实施例21：制造含有化合物13的有机电致发光器件
将实施例19中的化合物1置换为化合物13，其他方法相同，制作含有化合物13的有机电致发光器件。
实施例22：制造含有化合物17的有机电致发光器件
将实施例19中的化合物1置换为化合物17，其他方法相同，制作含有化合物17的有机电致发光器件。
实施例23：制造含有化合物18的有机电致发光器件
将实施例19中的化合物1置换为化合物18，其他方法相同，制作含有化合物18的有机电致发光器件。
实施例24：制造含有化合物20的有机电致发光器件
将实施例19中的化合物1置换为化合物20，其他方法相同，制作含有化合物20的有机电致发光器件。
实施例25：制造含有化合物28的有机电致发光器件
将实施例19中的化合物1置换为化合物28，其他方法相同，制作含有化合物28的有机电致发光器件。
实施例26：制造含有化合物31的有机电致发光器件
将实施例19中的化合物1置换为化合物31，其他方法相同，制作含有化合物31的有机电致发光器件。
实施例27：制造含有化合物35的有机电致发光器件
将实施例19中的化合物1置换为化合物35，其他方法相同，制作含有化合物35的有机电致发光器件。
实施例28：制造含有化合物40的有机电致发光器件
将实施例19中的化合物1置换为化合物40，其他方法相同，制作含有化合物40的有机电致发光器件。
实施例29：制造含有化合物41的有机电致发光器件
将实施例198中的化合物1置换为化合物41，其他方法相同，制作含有化合物41的有机电致发光器件。
实施例30：制造含有化合物42的有机电致发光器件
将实施例19中的化合物1置换为化合物42，其他方法相同，制作含有化合物42的有机电致发光器件。
实施例31：制造含有化合物45的有机电致发光器件
将实施例19中的化合物1置换为化合物45，其他方法相同，制作含有化合物45的有机电致发光器件。
实施例32：制造含有化合物46的有机电致发光器件
将实施例19中的化合物1置换为化合物46，其他方法相同，制作含有化合物46的有机电致发光器件。
实施例33：制造含有化合物51的有机电致发光器件
将实施例19中的化合物1置换为化合物51，其他方法相同，制作含有化合物51的有机电致发光器件。
实施例34：制造含有化合物54的有机电致发光器件
将实施例19中的化合物1置换为化合物54，其他方法相同，制作含有化合物54的有机电致发光器件。
实施例35：制造含有化合物61的有机电致发光器件
将实施例19中的化合物1置换为化合物61，其他方法相同，制作含有化合物61的有机电致发光器件。
实施例36：制造含有化合物77的有机电致发光器件
将实施例19中的化合物1置换为化合物77，其他方法相同，制作含有化合物77的有机电致发光器件。
对比例1：
按照实施例19的方法，将空穴传输层的材料由化合物1置换为N'-二(1-萘基)-N,N'-二苯基-(1,1'-联苯)-4,4'-二胺(NPD)。
用热重分析法测量实施例1～18合成的化合物的热分解温度。应用差示扫描量热法测量上述化合物的玻璃化转变温度Tg。结果如表1所示。
表1
表2为本发明实施例制备的化合物以及a-NPD制备的有机电致发光器件的发光特性测试结果。
表2
从上表可看出本发明提供的化合物有适合的玻璃态转变温度，由其制备的有机电致发光器件的发光效率及寿命相对于由a-NPD制备的有机电致发光器件有显著的提高。
以上实施例的说明只是用于帮助理解本发明的方法及其核心思想。应当指出，对于本技术领域的普通技术人员来说，在不脱离本发明原理的前提下，还可以对本发明进行若干改进和修饰，这些改进和修饰也落入本发明权利要求的保护范围内。

Claims (10)

1.一种有机发光化合物，其特征在于，其结构式如下：
式中：Ar1和Ar2各自独立地表示经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3-30元杂芳基；或与相邻取代基连接形成单环或C3-C30多环脂环族环或芳香族环，其碳原子还可置换为至少一个选自氮、氧和硫的杂原子；
L表示苯基；
G环表示经取代或未经取代的C3-C30环烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3-30元杂芳基；
G环可以存在也可以不存在；
当G环不存在时X、Y、Z表示-O-、-S-、-SO2-、-C(R5)(R6)-、-N(R7)-、-Si-、-Sn-或者-Ge-；
当G环存在时X表示-SO2-、-N(R7)-、-Si-、-Sn-或者-Ge-；Y、Z表示C原子；
R1到R4各自独立地表示氢、氘、卤素、氰基、羧基、硝基、羟基、经取代或未经取代的C1-C30烃基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C3-C30环烯基、经取代或未经取代的3-7元杂环烷基、经取代或未经取代的C6-C30芳基、经取代或未经取代的3-30元杂芳基、-NR8R9、-SiR10R11R12、-SR13、-OR14、-COR15或者-B(OR16)(OR17)；或与相邻取代基连接形成经取代或未经取代的单环或C3-C30多环脂肪族环或芳香族环，其碳原子还可置换成至少一个选自氮、氧和硫的杂原子；
R5到R17各自独立地表示氢、经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3到30元杂芳基；或与相邻取代基连接形成经取代或未经取代的单环或C3-C30多环脂肪族环或芳香族环；
a、b和d各自独立地表示整数1到4；
c表示整数1到3。
2.根据权利要求1所述的有机发光化合物，其特征在于，Ar1和Ar2各自独立地表示经取代或未经取代的C10-C25芳基，13-25元杂芳基。
3.根据权利要求1所述的有机发光化合物，其特征在于，Ar1和Ar2各自独立地表示经取代或未经取代的C14-C21芳基，17-23元杂芳基。
4.根据权利要求1所述的有机发光化合物，其特征在于，Ar1和Ar2各自独立地表示经取代或未经取代的C16-C19芳基，19-21元杂芳基。
5.根据权利要求1所述的有机发光化合物，其特征在于，选自下述结构中的任意一个：
6.一种权利要求1所述的有机发光化合物的制法，其特征在于，包括以下步骤：
步骤1、将化合物2加入到THF中溶解，在氮气气氛下将反应液冷却到-78℃，接着加入n-BuLi，在-78℃搅拌混合物至均匀，再在室温下搅拌，再冷却-78℃；将化合物1加入到THF中溶解，并将该混合溶液加入到前述化合物2的混合溶液中，并将温度升至室温后继续进行搅拌反应，接着将氯化铵水溶液添加到反应溶液中以完成反应，并且用乙酸乙酯萃取反应溶液，接着再使用硫酸镁干燥经萃取的有机物层，并且使用旋转式蒸发器去除溶剂，用管柱色谱法纯化剩余物质获得中间体1；
步骤2、将中间体1、化合物3和二氯甲烷加入到反应容器中之后，用氮气充分置换空气三次；将溶解于二氯甲烷中的三氟化硼乙醚逐滴添加到混合物中；在室温下进行搅拌反应，反应结束后用蒸馏水淬灭，并且用二氯甲烷萃取混合物；接着使用硫酸钠干燥萃取的有机物层，并且使用旋转式蒸发器去除溶剂，用柱色谱法纯化剩余物质获得式1化合物；
其合成路线如下：
其中：Ar1和Ar2各自独立地表示经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3-30元杂芳基；或与相邻取代基连接形成单环或C3-C30多环脂环族环或芳香族环，其碳原子还可置换为至少一个选自氮、氧和硫的杂原子；L表示苯基；G环表示经取代或未经取代的C3-C30环烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3-30元杂芳基；G环可以存在也可以不存在；当G环不存在时X、Y、Z表示-O-、-S-、-SO2-、-C(R5)(R6)-、-N(R7)-、-Si-、-Sn-或者-Ge-；当G环存在时X表示-SO2-、-N(R7)-、-Si-、-Sn-或者-Ge-；Y、Z表示C原子；R1到R4各自独立地表示氢、氘、卤素、氰基、羧基、硝基、羟基、经取代或未经取代的C1-C30烃基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C3-C30环烯基、经取代或未经取代的3-7元杂环烷基、经取代或未经取代的C6-C30芳基、经取代或未经取代的3-30元杂芳基、-NR8R9、-SiR10R11R12、-SR13、-OR14、-COR15或者-B(OR16)(OR17)；或与相邻取代基连接形成经取代或未经取代的单环或C3-C30多环脂肪族环或芳香族环，其碳原子还可置换成至少一个选自氮、氧和硫的杂原子；R5到R17各自独立地表示氢、经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C30芳基、或经取代或未经取代的3到30元杂芳基；或与相邻取代基连接形成经取代或未经取代的单环或C3-C30多环脂肪族环或芳香族环；a、b和d各自独立地表示整数1到4；c表示整数1到3，Hal为卤素。
7.一种含有权利要求1-5任意一项所述的有机发光化合物的有机电致发光器件。
8.根据权利要求7所述的有机电致发光器件，其特征在于，包括：
第一电极、第二电极和置于所述两电极之间的有机物层，其中，所述有机物层中包含有式1所示结构的化合物；式1所示结构的化合物可以是单一形态或与其它物质混合存在于有机物层中。
9.根据权利要求8所述的有机电致发光器件，其特征在于，所述有机物层至少包括空穴注入层，空穴传输层，既具备空穴注入又具备空穴传输技能层，电子阻挡层，发光层，空穴阻挡层，电子传输层，电子注入层和既具备电子传输又具备电子注入技能层中的一种或几种。
10.根据权利要求7-9任一项所述的有机电致发光器件可以用于有机发光器件、有机太阳电池、电子纸、有机感光体或有机薄膜晶体管。
CN201811180929.1A 2018-10-11 2018-10-11 一种有机发光化合物及制法和含该化合物的有机电致发光器件 Pending CN109180560A (zh)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN201811180929.1A CN109180560A (zh) 2018-10-11 2018-10-11 一种有机发光化合物及制法和含该化合物的有机电致发光器件
PCT/CN2019/078284 WO2020073605A1 (zh) 2018-10-11 2019-03-15 一种有机发光化合物及制法和含该化合物的有机电致发光器件

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201811180929.1A CN109180560A (zh) 2018-10-11 2018-10-11 一种有机发光化合物及制法和含该化合物的有机电致发光器件

Publications (1)

Publication Number Publication Date
CN109180560A true CN109180560A (zh) 2019-01-11

Family

ID=64948020

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201811180929.1A Pending CN109180560A (zh) 2018-10-11 2018-10-11 一种有机发光化合物及制法和含该化合物的有机电致发光器件

Country Status (1)

Country Link
CN (1) CN109180560A (zh)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109776393A (zh) * 2019-03-12 2019-05-21 上海升翕光电科技有限公司 一种有机发光化合物及制法和该化合物的有机电致发光器件
CN109970576A (zh) * 2019-04-22 2019-07-05 吉林奥来德光电材料股份有限公司 一种有机电致发光化合物及其制备方法和应用
WO2020073605A1 (zh) * 2018-10-11 2020-04-16 上海升翕光电科技有限公司 一种有机发光化合物及制法和含该化合物的有机电致发光器件
WO2021025371A1 (ko) * 2019-08-02 2021-02-11 덕산네오룩스 주식회사 유기전기소자
CN112939787A (zh) * 2019-12-10 2021-06-11 北京鼎材科技有限公司 一种化合物及其应用
CN113214237A (zh) * 2021-05-15 2021-08-06 吉林奥来德光电材料股份有限公司 一种有机电致发光材料及其制备方法与应用
CN113336785A (zh) * 2021-06-25 2021-09-03 长春海谱润斯科技股份有限公司 一种含硅芴的芳香胺类化合物及其有机电致发光器件
CN113735759A (zh) * 2021-09-26 2021-12-03 长春海谱润斯科技股份有限公司 一种二胺衍生物及其有机电致发光器件
CN116134030A (zh) * 2020-08-24 2023-05-16 株式会社Lg化学 新型化合物及包含其的有机发光器件
CN116323574A (zh) * 2020-09-17 2023-06-23 株式会社Lg化学 新型化合物及包含其的有机发光器件

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009035296A2 (en) * 2007-09-14 2009-03-19 Cheil Industries Inc. Organic compound, and organic photoelectric device including the same
CN105579551A (zh) * 2013-10-02 2016-05-11 罗门哈斯电子材料韩国有限公司 有机电致发光化合物和包含所述化合物的有机电致发光装置
CN107739428A (zh) * 2017-09-04 2018-02-27 华南理工大学 侧链含空穴传输单元的聚（芴‑co‑S,S‑二氧‑二苯并噻吩）衍生物及其制法与应用

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009035296A2 (en) * 2007-09-14 2009-03-19 Cheil Industries Inc. Organic compound, and organic photoelectric device including the same
CN105579551A (zh) * 2013-10-02 2016-05-11 罗门哈斯电子材料韩国有限公司 有机电致发光化合物和包含所述化合物的有机电致发光装置
CN107739428A (zh) * 2017-09-04 2018-02-27 华南理工大学 侧链含空穴传输单元的聚（芴‑co‑S,S‑二氧‑二苯并噻吩）衍生物及其制法与应用

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020073605A1 (zh) * 2018-10-11 2020-04-16 上海升翕光电科技有限公司 一种有机发光化合物及制法和含该化合物的有机电致发光器件
CN109776393A (zh) * 2019-03-12 2019-05-21 上海升翕光电科技有限公司 一种有机发光化合物及制法和该化合物的有机电致发光器件
CN109970576A (zh) * 2019-04-22 2019-07-05 吉林奥来德光电材料股份有限公司 一种有机电致发光化合物及其制备方法和应用
CN109970576B (zh) * 2019-04-22 2022-04-01 吉林奥来德光电材料股份有限公司 一种有机电致发光化合物及其制备方法和应用
WO2021025371A1 (ko) * 2019-08-02 2021-02-11 덕산네오룩스 주식회사 유기전기소자
CN114207861A (zh) * 2019-08-02 2022-03-18 德山新勒克斯有限公司 有机电子器件
CN112939787A (zh) * 2019-12-10 2021-06-11 北京鼎材科技有限公司 一种化合物及其应用
CN116134030A (zh) * 2020-08-24 2023-05-16 株式会社Lg化学 新型化合物及包含其的有机发光器件
CN116323574A (zh) * 2020-09-17 2023-06-23 株式会社Lg化学 新型化合物及包含其的有机发光器件
CN113214237A (zh) * 2021-05-15 2021-08-06 吉林奥来德光电材料股份有限公司 一种有机电致发光材料及其制备方法与应用
CN113336785A (zh) * 2021-06-25 2021-09-03 长春海谱润斯科技股份有限公司 一种含硅芴的芳香胺类化合物及其有机电致发光器件
CN113735759A (zh) * 2021-09-26 2021-12-03 长春海谱润斯科技股份有限公司 一种二胺衍生物及其有机电致发光器件

Similar Documents

Publication Publication Date Title
CN109180560A (zh) 一种有机发光化合物及制法和含该化合物的有机电致发光器件
CN109748898B (zh) 有机电致发光化合物及其制备方法和有机电致发光器件
CN109748802A (zh) 一种有机电致发光化合物及制法和有机电致发光器件
CN102803437B (zh) 用于有机光电装置的化合物和有机光电装置
CN103570737B (zh) 杂环化合物，包含其的有机发光装置和有机发光显示器
TWI443176B (zh) 發光元件材料及發光元件
CN109776393A (zh) 一种有机发光化合物及制法和该化合物的有机电致发光器件
CN109796960A (zh) 一种有机电致发光化合物及制法和应用
CN112062718B (zh) 有机电致发光化合物和包含所述化合物的有机电致发光装置
CN105461611A (zh) 螺芴苄基荧光材料
CN104673276B (zh) 一种有机发光材料及其应用
CN109970575A (zh) 有机电致发光化合物及其制法和应用
CN100494209C (zh) 一种有机电致发光材料及其应用
CN109776334B (zh) 有机电致发光化合物及其制法和器件
CN110078754A (zh) 化合物、显示面板以及显示装置
CN110526901A (zh) 一种有机发光材料及其制备有机电致发光器件的应用
Gu et al. Tetrasubstituted adamantane derivatives with arylamine groups: Solution-processable hole-transporting and host materials with high triplet energy and good thermal stability for organic light-emitting devices
CN107652272A (zh) 一种以酮类结构为母核的有机化合物及其在oled器件中的应用
CN107056763A (zh) 一种以氧杂蒽为核心的有机电致发光材料及其应用
CN104592978A (zh) 苯并蒽芴基蓝光磷光主体材料及其制备方法和应用
CN109574909A (zh) 一种以酮类结构为核心的有机化合物及其在oled器件中的应用
CN109970645A (zh) 含氮杂环有机电致发光化合物及其制法和有机电致发光器件
CN111808125B (zh) 一种有机化合物、有机电致发光材料及其应用
CN111377966A (zh) 一种化合物及其应用、包含其的有机电致发光器件
CN109293583A (zh) 一种含喹唑啉杂环化合物及其在有机光电器件中的应用

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
RJ01 Rejection of invention patent application after publication
RJ01 Rejection of invention patent application after publication

Application publication date: 20190111