CN110845422A - Organic light-emitting compound, synthetic method thereof and organic electroluminescent device - Google Patents

Organic light-emitting compound, synthetic method thereof and organic electroluminescent device Download PDF

Info

Publication number
CN110845422A
CN110845422A CN201911192500.9A CN201911192500A CN110845422A CN 110845422 A CN110845422 A CN 110845422A CN 201911192500 A CN201911192500 A CN 201911192500A CN 110845422 A CN110845422 A CN 110845422A
Authority
CN
China
Prior art keywords
substituted
unsubstituted
organic light
organic
reaction
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.)
Withdrawn
Application number
CN201911192500.9A
Other languages
Chinese (zh)
Inventor
汪康
孙向南
王士凯
孙毅
金成寿
徐佳楠
马晓宇
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 CN201911192500.9A priority Critical patent/CN110845422A/en
Publication of CN110845422A publication Critical patent/CN110845422A/en
Withdrawn legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • C07D213/22—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 two or more pyridine rings directly linked together, e.g. bipyridyl
    • 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
    • C07D215/06—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 having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
    • 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
    • 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
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • 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
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—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
    • C09K2211/1059—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

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

The invention discloses an organic luminescent compound, a synthetic method thereof and an organic electroluminescent device, belonging to the fields of chemical synthesis and photoelectric materials. The general structural formula of the organic light-emitting compound is as follows:in the formula, Ar1、Ar2Each independently is one of hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C1-C8 alkoxy, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C6-C30 aryl, C6-C30 aryloxy and substituted or unsubstituted C4-C12 heteroaryl; l is1Is one of chemical bonds, substituted or unsubstituted C6-C12 aryl, and substituted or unsubstituted C6-C12 heteroaryl. The organic luminescent compound is used as a material of a luminescent layer or an electron transport layer of an organic electroluminescent device, so that the driving voltage of the organic electroluminescent device can be remarkably reduced and the driving voltage of the organic electroluminescent device can be improvedThe luminous efficiency and the service life of the organic electroluminescent device.

Description

Organic light-emitting compound, synthetic method thereof and organic electroluminescent device
Technical Field
The invention relates to the field of chemical synthesis and photoelectric materials, in particular to an organic light-emitting compound, a synthesis method thereof and an organic electroluminescent device.
Background
Organic electroluminescence is a light-emitting phenomenon in which an organic material directly converts electric energy into light energy under the action of an electric field, and has been gradually applied to smart phones, flat-panel televisions, and virtual reality commodities.
At present, factors such as efficiency and lifetime of an organic electroluminescent device restrict the development of the device, and in order to improve the brightness, efficiency and lifetime of the organic electroluminescent device, a multilayer structure is generally used in the device. These multilayer structures typically include: a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, and the like.
In the organic material, the transfer rates of electrons and holes are different, and if an appropriate material is used, the electrons and holes are effectively transferred to the light-emitting layer, and the number of the electrons and holes is balanced, so that the light-emitting efficiency can be effectively improved. Suitable materials are however very difficult to find. Among them, tris (8-hydroxyquinoline) aluminum (Alq3) has been used as an electron transport material for nearly 30 years since the invention, and there are many data that prove it is superior to conventional materials. However, as an electron transport material, it still has the problems of low luminous efficiency and short service life.
Disclosure of Invention
An object of an embodiment of the present invention is to provide an organic light emitting compound to solve the problems set forth in the background art described above.
In order to achieve the above purpose, the embodiments of the present invention provide the following technical solutions:
an organic light-emitting compound having a general structural formula of formula I:
Figure BDA0002293917990000021
in the formula I, Ar1、Ar2Each independently is one of hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C1-C8 alkoxy, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C6-C30 aryl, C6-C30 aryloxy and substituted or unsubstituted C4-C12 heteroaryl;
L1is one of chemical bonds, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C12 heteroaryl;
R1independently hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and one of a C3-C30 aliphatic ring or aromatic ring which is connected with adjacent substituents to form a single ring or multiple rings; at least one carbon atom in the C3-C30 aliphatic ring or aromatic ring which is connected with the adjacent substituent to form a single ring or multiple rings is replaced or not replaced by a heteroatom;
a is one of hydrogen, substituted or unsubstituted aryl of C6-C60, substituted or unsubstituted heteroaryl of C6-C60, substituted or unsubstituted condensed ring group of C10-C60 and spiro ring group of C10-C60.
Wherein the term "substituted or unsubstituted" means substituted with one, two or more substituents selected from: deuterium; a halogen group; a nitrile group; a hydroxyl group; a carbonyl group; an ester group; a silyl group; a boron group; substituted or unsubstituted alkyl; substituted or unsubstituted cycloalkyl; substituted or unsubstituted alkoxy; substituted or unsubstituted alkenyl; substituted or unsubstituted alkylamino; substituted or unsubstituted heteroarylamino; substituted or unsubstituted arylamine; substituted or unsubstituted aryl; substituted or unsubstituted heterocyclyl; or a substituent in which two or more substituents among the above-shown substituents are linked, or no substituent. For example, "a substituent in which two or more substituents are linked" may include a biphenyl group. In other words, biphenyl can be an aryl group, or can be interpreted as a substituent with two phenyl groups attached.
As a preferred embodiment of the present invention, Ar1、Ar2Each independently is one of benzene and its derivatives, naphthalene and its derivatives, anthracene and its derivatives, phenanthrene and its derivatives, pyrene and its derivatives, biphenyl and its derivatives, imidazole and its derivatives, oxazole and its derivatives, thiazole and its derivatives, furan and its derivatives.
In another preferred embodiment of the present invention, the heterocyclic group is an aromatic or non-aromatic cyclic group containing at least one heteroatom.
As another preferable mode of the embodiment of the present invention, the heteroatom is one of O, S, N, P, B, Si and Se.
As another preferable mode of the embodiment of the present invention, the heteroatom is one of O, S and N.
In another preferred embodiment of the present invention, the heterocyclic group is one of morpholinyl, piperidinyl, pyrrolidinyl, tetrahydrofuran, tetrahydropyran and tetrahydrothiophene.
As another preferable mode of the embodiment of the present invention, the organic light emitting compound has a chemical structural formula of one of formulae 1 to 80:
Figure BDA0002293917990000031
Figure BDA0002293917990000041
Figure BDA0002293917990000051
Figure BDA0002293917990000061
Figure BDA0002293917990000071
Figure BDA0002293917990000081
another object of an embodiment of the present invention is to provide a method for synthesizing the organic light emitting compound, including the following steps:
under the protection atmosphere, adding a first reactant with a general formula II, a second reactant with a general formula III, tetrakis (triphenylphosphine) palladium and potassium carbonate into a mixed solvent for heating reflux reaction, washing and filtering, and then putting into 1, 4-dioxane for recrystallization to obtain a first intermediate;
adding the first intermediate into N, N-dimethylformamide, and adding N-bromosuccinimide for reaction to obtain a first reaction solution; dripping the first reaction liquid into petroleum ether, separating out solid, and performing suction filtration and drying treatment to obtain a second intermediate;
under the protective atmosphere, adding a second intermediate, a third reactant with a general formula IV, tetrakis (triphenylphosphine) palladium and potassium carbonate into a mixed solvent, heating, carrying out reflux reaction, washing, filtering, and then putting into 1, 4-dioxane for recrystallization to obtain a third intermediate;
adding the third intermediate into N, N-dimethylformamide, and adding N-bromosuccinimide for reaction to obtain a second reaction solution; dripping the second reaction liquid into petroleum ether, separating out solid, and performing suction filtration and drying treatment to obtain a fourth intermediate;
and adding a fourth intermediate, a fourth reactant with a general formula V, tetrakis (triphenylphosphine) palladium and potassium carbonate into a mixed solvent for heating reflux reaction, washing, filtering, and then putting into 1, 4-dioxane for recrystallization to obtain the organic luminescent compound.
Wherein, the chemical synthesis route of the organic luminous compound is as follows:
Figure BDA0002293917990000101
wherein A is a first reactant, B is a second reactant, C is a first intermediate, D is a second intermediate, E is a third reactant, F is a third intermediate, G is a fourth intermediate, H is a fourth reactant, and the final product is the organic light-emitting compound. In addition, Ar appearing in the scheme1、Ar1、R1、L1The same ranges as described in the above general formula I.
As another preferable mode of the embodiment of the present invention, the mixed solvent includes toluene, ethanol and water.
Preferably, the volume ratio of the toluene to the ethanol to the water is (2-4): 0.8-1.2): 1.
Preferably, the molar ratio of the first reactant, the second reactant, the palladium tetrakis (triphenylphosphine) and the potassium carbonate is 100 (100-120): (0.8-1.2): 130-150.
Preferably, the molar ratio of the fourth intermediate, the fourth reactant, the tetrakis (triphenylphosphine) palladium and the potassium carbonate is 40 (40-50): (0.3-0.5): 130-150.
Another object of an embodiment of the present invention is to provide an organic electroluminescent device, which includes at least one organic layer, where the organic layer includes a light emitting layer and/or an electron transport layer; the light-emitting layer and the electron transport layer respectively comprise the organic light-emitting compound.
Compared with the prior art, the embodiment of the invention has the beneficial effects that:
the embodiment of the invention provides a novel organic light-emitting compound, and the organic light-emitting compound is used as a material of a light-emitting layer or an electron transport layer of an organic electroluminescent device, so that the driving voltage of the organic electroluminescent device can be remarkably reduced, the light-emitting efficiency of the organic electroluminescent device can be improved, the service life of the organic electroluminescent device can be prolonged, and the practicability of the organic electroluminescent device can be improved. In addition, the organic luminescent compound provided by the embodiment of the invention has the advantages of short synthetic route, simple process, easily obtained raw materials and low cost, and is suitable for industrial production.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
This example provides an organic light-emitting compound, whose chemical structural formula is formula 5 in the summary of the invention, and the reaction route of the synthesis method of the organic light-emitting compound is as follows:
Figure BDA0002293917990000111
the specific synthesis method comprises the following steps:
(1) under a nitrogen protective atmosphere, a reactant A-5(100mmoL), a reactant B-5(110mmoL), tetrakis (triphenylphosphine) palladium (1.1mmoL) and potassium carbonate (144mmoL) were added to a mixed solvent of toluene (150mL), ethanol (50mL) and water (50mL), respectively, the mixture was heated to reflux to carry out a reaction, after the reaction was completed, the mixture was cooled to room temperature again, water was added thereto to wash, filter and dry a filter cake, and the dried filter cake was then placed in 1, 4-dioxane (150mL) to be recrystallized, thereby obtaining a compound represented by an intermediate C-5 (30.9g, yield 83%).
(2) Adding the intermediate C-5(80mmol) into an N, N-dimethylformamide solvent, adding N-bromosuccinimide (90mmol), and stirring at room temperature to react to obtain a first reaction solution. After the reaction, the first reaction solution was concentrated to a small amount, slowly dropped into petroleum ether being stirred, and after the solid was completely precipitated, suction filtration and drying were carried out to obtain a compound represented by intermediate D-5 (31.3g, yield 87%).
(3) Under a nitrogen atmosphere, intermediate D-5(64mmoL), reactant E-5(77mmoL), tetrakis (triphenylphosphine) palladium (0.7mmoL) and potassium carbonate (144mmoL) were added to a mixed solvent of toluene (150mL), ethanol (50mL) and water (50mL), respectively, and the mixture was heated to reflux to carry out a reaction, and after the reaction was completed, the mixture was cooled to room temperature again, washed with water, filtered, and the filter cake was dried, and then recrystallized (150mL) in 1, 4-dioxane to obtain a compound represented by intermediate F-5 (25.8g, yield 81%).
(4) Adding the intermediate F-5(50mmoL) into an N, N-dimethylformamide solvent, and adding N-bromosuccinimide (55mmoL) to carry out stirring reaction at room temperature to obtain a second reaction solution. After the reaction is finished, the second reaction solution is concentrated to a little, slowly dropped into the petroleum ether which is being stirred, after the solid is completely separated out, the filtration and drying are carried out, and the intermediate G-5(24.5G, yield 85%) is obtained.
(5) Under the protection atmosphere of nitrogen, respectively adding the intermediate G-5(40mmoL), the reactant H-5(45mmoL), the tetrakis (triphenylphosphine) palladium (0.4mmoL) and the potassium carbonate (144mmoL) into a mixed solvent of toluene (150mL), ethanol (50mL) and water (50mL), heating to reflux for reaction, cooling to room temperature after the reaction is finished, adding water for washing, filtering, drying a filter cake, and then putting into 1, 4-dioxane for recrystallization to obtain a final product 5(21.0G, yield 84%), namely the organic light-emitting compound.
Example 2
This example provides an organic light-emitting compound having a chemical structural formula of formula 25 in the summary of the invention, and the reaction route of the synthesis method of the organic light-emitting compound is as follows:
the specific synthesis method comprises the following steps:
(1) under a nitrogen atmosphere, a reactant A-25(100mmoL), a reactant B-25(110mmoL), tetrakis (triphenylphosphine) palladium (1.1mmoL) and potassium carbonate (144mmoL) were added to a mixed solvent of toluene (150mL), ethanol (50mL) and water (50mL), respectively, the mixture was heated to reflux to carry out a reaction, after the reaction was completed, the mixture was cooled to room temperature again, water was added thereto to wash, filter and dry a filter cake, and the dried filter cake was then placed in 1, 4-dioxane (150mL) to carry out recrystallization, thereby obtaining a compound represented by an intermediate C-25 (32.0g, yield 84%).
(2) Adding the intermediate C-25(80mmol) into an N, N-dimethylformamide solvent, adding N-bromosuccinimide (90mmol), and stirring at room temperature to react to obtain a first reaction solution. After the reaction was completed, the first reaction solution was concentrated to a small amount, and slowly dropped into petroleum ether being stirred, and after the solid was completely precipitated, suction filtration and drying were performed to obtain a compound represented by intermediate D-25 (31.6g, yield 86%).
(3) Under a nitrogen atmosphere, intermediate D-25(64mmoL), reactant E-25(77mmoL), tetrakis (triphenylphosphine) palladium (0.7mmoL) and potassium carbonate (144mmoL) were added to a mixed solvent of toluene (150mL), ethanol (50mL) and water (50mL), respectively, and the mixture was heated to reflux to carry out a reaction, and after the reaction was completed, the mixture was cooled to room temperature again, washed with water, filtered, and the filter cake was dried, and then recrystallized (150mL) in 1, 4-dioxane to obtain a compound represented by intermediate F-25 (24.3g, yield 83%).
(4) Adding the intermediate F-25(50mmoL) into an N, N-dimethylformamide solvent, and adding N-bromosuccinimide (55mmoL) to carry out stirring reaction at room temperature to obtain a second reaction solution. After the reaction is finished, the second reaction solution is concentrated to a little and slowly dripped into petroleum ether which is being stirred, after the solid is completely separated out, the filtration and drying are carried out, and the intermediate G-25(22.7G, yield 85%) is obtained.
(5) Under the protection atmosphere of nitrogen, respectively adding the intermediate G-25(40mmoL), the reactant H-25(45mmoL), the tetrakis (triphenylphosphine) palladium (0.4mmoL) and the potassium carbonate (144mmoL) into a mixed solvent of toluene (150mL), ethanol (50mL) and water (50mL), heating to reflux for reaction, cooling to room temperature after the reaction is finished, adding water for washing, filtering, drying a filter cake, and then putting into 1, 4-dioxane for recrystallization to obtain a final product 25(17.5G, the yield is 82%), namely the organic light-emitting compound.
Example 3
This example provides an organic light-emitting compound having a chemical structural formula shown in formula 38 of the summary of the invention, and the reaction route of the synthesis method of the organic light-emitting compound is as follows:
Figure BDA0002293917990000151
the specific synthesis method comprises the following steps:
(1) under a nitrogen atmosphere, a reactant A-38(100mmoL), a reactant B-38(110mmoL), tetrakis (triphenylphosphine) palladium (1.1mmoL) and potassium carbonate (144mmoL) were added to a mixed solvent of toluene (150mL), ethanol (50mL) and water (50mL), respectively, the mixture was heated to reflux to carry out a reaction, after the reaction was completed, the mixture was cooled to room temperature again, water was added thereto to wash, filter and dry a filter cake, and the dried filter cake was recrystallized in 1, 4-dioxane (150mL) to obtain a compound represented by an intermediate C-38 (35.4g, yield 82%).
(2) Adding the intermediate C-38(80mmol) into an N, N-dimethylformamide solvent, adding N-bromosuccinimide (90mmol), and stirring at room temperature to react to obtain a first reaction solution. After the reaction was completed, the first reaction solution was concentrated to a small amount, and slowly dropped into petroleum ether being stirred, and after the solid was completely precipitated, suction filtration and drying were carried out to obtain a compound represented by intermediate D-38 (35.9g, yield 88%).
(3) Under a nitrogen atmosphere, intermediate D-38(64mmoL), reactant E-38(77mmoL), tetrakis (triphenylphosphine) palladium (0.7mmoL) and potassium carbonate (144mmoL) were added to a mixed solvent of toluene (150mL), ethanol (50mL) and water (50mL), respectively, and the mixture was heated to reflux to carry out a reaction, and after the reaction was completed, the mixture was cooled to room temperature again, washed with water, filtered, and the filter cake was dried, and then recrystallized (150mL) in 1, 4-dioxane to obtain a compound represented by intermediate F-38 (28.9g, yield 81%).
(4) Adding the intermediate F-38(50mmoL) into an N, N-dimethylformamide solvent, and adding N-bromosuccinimide (55mmoL) to carry out stirring reaction at room temperature to obtain a second reaction solution. After the reaction is finished, the second reaction solution is concentrated to a little, slowly dropped into the petroleum ether which is being stirred, after the solid is completely separated out, suction filtration and drying are carried out, and the intermediate G-38(27G, yield 85%) is obtained.
(5) Under the protection atmosphere of nitrogen, respectively adding the intermediate G-38(40mmoL), the reactant H-38(45mmoL), tetrakis (triphenylphosphine) palladium (0.4mmoL) and potassium carbonate (144mmoL) into a mixed solvent of toluene (150mL), ethanol (50mL) and water (50mL), heating to reflux for reaction, cooling to room temperature after the reaction is finished, adding water for washing, filtering, drying a filter cake, and then putting into 1, 4-dioxane for recrystallization to obtain a final product 38(23.0G, yield 84%), namely the organic light-emitting compound.
Example 4
This example provides an organic light-emitting compound having a chemical structural formula of formula 56 in the summary of the invention, and the reaction route of the synthesis method of the organic light-emitting compound is as follows:
Figure BDA0002293917990000171
the specific synthesis method comprises the following steps:
(1) under a nitrogen atmosphere, a reactant A-56(100mmoL), a reactant B-56(110mmoL), tetrakis (triphenylphosphine) palladium (1.1mmoL) and potassium carbonate (144mmoL) were added to a mixed solvent of toluene (150mL), ethanol (50mL) and water (50mL), respectively, the mixture was heated to reflux to carry out a reaction, after the reaction was completed, the mixture was cooled to room temperature again, water was added thereto to wash, filter and dry a filter cake, and the dried filter cake was recrystallized in 1, 4-dioxane (150mL) to obtain a compound represented by an intermediate C-56 (40.3g, yield 83%).
(2) Adding the intermediate C-56(80mmol) into an N, N-dimethylformamide solvent, adding N-bromosuccinimide (90mmol), and stirring at room temperature to react to obtain a first reaction solution. After the reaction was completed, the first reaction solution was concentrated to a small amount, and slowly dropped into petroleum ether being stirred, and after the solid was completely precipitated, suction filtration and drying were carried out to obtain a compound represented by intermediate D-56 (38.7g, yield 86%).
(3) Under a nitrogen atmosphere, intermediate D-56(64mmoL), reactant E-56(77mmoL), tetrakis (triphenylphosphine) palladium (0.7mmoL) and potassium carbonate (144mmoL) were added to a mixed solvent of toluene (150mL), ethanol (50mL) and water (50mL), respectively, and the mixture was heated to reflux to carry out a reaction, and after the reaction was completed, the mixture was cooled to room temperature, washed with water, filtered, and the filter cake was dried, and then recrystallized (150mL) in 1, 4-dioxane to obtain a compound represented by intermediate F-56 (32.1g, yield 82%).
(4) Adding the intermediate F-56(50mmoL) into an N, N-dimethylformamide solvent, adding N-bromosuccinimide (55mmoL), and stirring at room temperature to react to obtain a second reaction solution. After the reaction is finished, the second reaction solution is concentrated to a little and slowly dripped into petroleum ether which is being stirred, after the solid is completely separated out, the filtration and drying are carried out, and the intermediate G-56(29.6G, yield 86%) is obtained.
(5) Under the protection atmosphere of nitrogen, respectively adding the intermediate G-56(40mmoL), the reactant H-56(45mmoL), the tetrakis (triphenylphosphine) palladium (0.4mmoL) and the potassium carbonate (144mmoL) into a mixed solvent of toluene (150mL), ethanol (50mL) and water (50mL), heating to reflux for reaction, cooling to room temperature after the reaction is finished, adding water for washing, filtering, drying a filter cake, and then putting into 1, 4-dioxane for recrystallization to obtain a final product 56(24.8G, yield 84%), namely the organic light-emitting compound.
According to the same principle and route as those of the above embodiments 1 to 4, the organic light emitting compounds of the present invention with the chemical structural formulas of 1, 6, 9, 21, 24, 30, 36, 40, 47, 51 and 75 are synthesized, and the molecular weights of the organic light emitting compounds are tested by mass spectrometry, wherein the corresponding molecular formulas, theoretical values of mass spectrometry and values of mass spectrometry are shown in table 1.
TABLE 1
Figure BDA0002293917990000181
Figure BDA0002293917990000191
Example 5
This embodiment provides an organic electroluminescent device prepared using the organic light-emitting compound provided in the above embodiment, wherein the organic electroluminescent device includes a first electrode, a second electrode, and at least one set of organic layers disposed between the first electrode and the second electrode.
When the organic layer includes a hole injection layer, a hole transport layer, and a layer having both hole injection and hole transport properties, it is preferable that at least one of the hole injection layer, the hole transport layer, and the layer having both hole injection and hole transport properties includes a hole injection material, a hole transport material, or a material having both hole injection and hole transport properties. When the organic layer is of a single-layer structure, the organic layer is a light-emitting layer, and when the organic layer is of a multilayer structure, the organic layer comprises a light-emitting layer; the light emitting layer preferably includes one or more of a phosphorescent host, a fluorescent host, a phosphorescent dopant material, and a fluorescent dopant material.
When the organic layer includes an electron transport layer, the electron transport layer may include the organic light emitting compound provided in the above embodiments.
In some embodiments of the present invention, the electron transport layer may further include a metal compound. The metal compound is not particularly limited as long as it is a substance for electron transport, which is well known to those skilled in the art.
When the organic layer includes both the light-emitting layer and the electron transport layer, the light-emitting layer and the electron transport layer may respectively include the organic light-emitting compound provided in the above embodiments having the same or different structures.
Specifically, the preparation method of the organic electroluminescent device comprises the following steps:
(1) coating thickness of Fisher company of
Figure BDA0002293917990000201
The ITO glass substrate is placed in distilled water for cleaning for 2 times, ultrasonic cleaning is carried out for 30min, the ITO glass substrate is repeatedly cleaned for 2 times by distilled water and is ultrasonically cleaned for 10min, after the cleaning by distilled water is finished, the ITO glass substrate is sequentially ultrasonically cleaned by solvents such as isopropanol, acetone, methanol and the like, then dried, transferred into a plasma cleaning machine, and cleaned for 5min to obtain an ITO transparent electrode, and the ITO transparent electrode is sent into an evaporation plating machine.
(2) 4,4' -tris [ 2-naphthylphenylamino ] triphenylamine (2-TNATA) was deposited onto the prepared ITO transparent electrode to a thickness of 80nm as a hole injection layer. N '-di (1-naphthyl) -N, N' -diphenyl- (1,1 '-biphenyl) -4,4' -diamine (NPB) having a thickness of 30nm was vacuum-evaporated on the formed hole injection layer as a hole transport layer.
(3) 4,4'-N, N' -Biphenyldicarbazole ("CBP") and a doping material Ir (bty) were vapor-deposited on the hole transport layer to a thickness of 20nm2and (5) acac. The weight ratio of host material to dopant material was 95: 5. Then, bis (2-methyl-8-hydroxyquinoline-N1, 08) - (1,1' -biphenyl-4-hydroxy) aluminum (BALq) as a hole-blocking layer was vacuum-evaporated on the above light-emitting layer to a thickness of 10 nm. Then, the organic light-emitting compound obtained in the above example was vacuum-deposited on the hole-blocking layer to a thickness of 40nm as an electron-transporting layer. Then, lithium fluoride was vacuum-deposited on the electron transport layer to a thickness of 0.5nm as an electron injection layer. And finally, evaporating aluminum with the thickness of 100nm as a cathode to complete the preparation of the organic electroluminescent device.
Referring to the above method, organic light emitting compounds having chemical structural formulas of 1, 6, 9, 21, 24, 25, 30, 36, 38, 40, 47, 51, 56, and 75 are respectively selected as electron transport layers, and corresponding organic electroluminescent devices are prepared.
Comparative example 1
This comparative example provides a conventional organic electroluminescent device, which was prepared in the same manner as in example 5, with the only difference that the organic luminescent compound used in the electron transport layer of the organic electroluminescent device was Alq3, which has the formula:
Figure BDA0002293917990000211
the organic electroluminescent devices obtained in example 5 and comparative example 1 were applied with a forward DC bias voltage, respectively, and the organic electroluminescent characteristics were measured using PR-650 photometric measuring equipment from Photo Research, and measured at 5000cd/m2The lifetime of T95 was measured at the reference gray scale using a lifetime measuring device of McScience, and the driving voltage, the luminous efficiency and the lifetime of T95 obtained by the measurement are shown in Table 2 below.
TABLE 2
Figure BDA0002293917990000212
Figure BDA0002293917990000221
As can be seen from table 2 above, the organic electroluminescent device manufactured by using the organic luminescent compound provided in the embodiment of the present invention as an electron transport layer has a significantly reduced driving voltage, and the luminous efficiency and lifetime are significantly improved, compared to the organic electroluminescent device manufactured by using the conventional organic luminescent compound Alq3 as an electron transport layer.
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.

Claims (8)

1. An organic light-emitting compound, wherein the structural formula of the organic light-emitting compound is formula I:
Figure FDA0002293917980000011
in the formula I, Ar1、Ar2Each independently is one of hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C3-C30 cycloalkyl, substituted or unsubstituted C3-C30 heterocycloalkyl, substituted or unsubstituted C1-C8 alkoxy, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted C6-C30 aryl, C6-C30 aryloxy and substituted or unsubstituted C4-C12 heteroaryl;
L1is one of chemical bonds, substituted or unsubstituted C6-C12 aryl, substituted or unsubstituted C6-C12 heteroaryl;
R1independently hydrogen, substituted or unsubstituted C1-C30 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, and one of a C3-C30 aliphatic ring or aromatic ring which is connected with adjacent substituents to form a single ring or multiple rings; at least one carbon atom in the C3-C30 aliphatic ring or aromatic ring which is connected with the adjacent substituent to form a single ring or multiple rings is replaced or not replaced by a heteroatom;
a is one of hydrogen, substituted or unsubstituted aryl of C6-C60, substituted or unsubstituted heteroaryl of C6-C60, substituted or unsubstituted condensed ring group of C10-C60 and spiro ring group of C10-C60.
2. The organic light-emitting compound according to claim 1, wherein Ar is Ar1、Ar2Each independently is one of benzene and its derivatives, naphthalene and its derivatives, anthracene and its derivatives, phenanthrene and its derivatives, pyrene and its derivatives, biphenyl and its derivatives, imidazole and its derivatives, oxazole and its derivatives, thiazole and its derivatives, furan and its derivatives.
3. An organic light-emitting compound according to claim 1, wherein the heteroatom is one of O, S, N, P, B, Si and Se.
4. An organic light-emitting compound according to claim 3, wherein the heteroatom is one of O, S and N.
5. The organic light-emitting compound of claim 1, wherein the chemical structural formula of the organic light-emitting compound is one of formula 1 to formula 80:
Figure FDA0002293917980000031
Figure FDA0002293917980000041
Figure FDA0002293917980000061
Figure FDA0002293917980000071
6. a method for synthesizing an organic light-emitting compound according to any one of claims 1 to 5, comprising the steps of:
Figure FDA0002293917980000072
under the protection atmosphere, adding a first reactant with a general formula II, a second reactant with a general formula III, tetrakis (triphenylphosphine) palladium and potassium carbonate into a mixed solvent for heating reflux reaction, washing and filtering, and then putting into 1, 4-dioxane for recrystallization to obtain a first intermediate;
adding the first intermediate into N, N-dimethylformamide, and adding N-bromosuccinimide for reaction to obtain a first reaction solution; dripping the first reaction liquid into petroleum ether, separating out solid, and performing suction filtration and drying treatment to obtain a second intermediate;
under the protective atmosphere, adding a second intermediate, a third reactant with a general formula IV, tetrakis (triphenylphosphine) palladium and potassium carbonate into a mixed solvent, heating, carrying out reflux reaction, washing, filtering, and then putting into 1, 4-dioxane for recrystallization to obtain a third intermediate;
adding the third intermediate into N, N-dimethylformamide, and adding N-bromosuccinimide for reaction to obtain a second reaction solution; dripping the second reaction liquid into petroleum ether, separating out solid, and performing suction filtration and drying treatment to obtain a fourth intermediate;
and adding a fourth intermediate, a fourth reactant with a general formula V, tetrakis (triphenylphosphine) palladium and potassium carbonate into a mixed solvent for heating reflux reaction, washing, filtering, and then putting into 1, 4-dioxane for recrystallization to obtain the organic luminescent compound.
7. The method as claimed in claim 6, wherein the mixed solvent comprises toluene, ethanol and water.
8. An organic electroluminescent device comprising at least one organic layer, wherein the organic layer comprises a light-emitting layer and/or an electron transport layer, wherein the light-emitting layer and the electron transport layer each comprise the organic light-emitting compound according to any one of claims 1 to 5.
CN201911192500.9A 2019-11-28 2019-11-28 Organic light-emitting compound, synthetic method thereof and organic electroluminescent device Withdrawn CN110845422A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201911192500.9A CN110845422A (en) 2019-11-28 2019-11-28 Organic light-emitting compound, synthetic method thereof and organic electroluminescent device

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201911192500.9A CN110845422A (en) 2019-11-28 2019-11-28 Organic light-emitting compound, synthetic method thereof and organic electroluminescent device

Publications (1)

Publication Number Publication Date
CN110845422A true CN110845422A (en) 2020-02-28

Family

ID=69606598

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201911192500.9A Withdrawn CN110845422A (en) 2019-11-28 2019-11-28 Organic light-emitting compound, synthetic method thereof and organic electroluminescent device

Country Status (1)

Country Link
CN (1) CN110845422A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111440156A (en) * 2020-05-07 2020-07-24 吉林奥来德光电材料股份有限公司 Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device
CN112939990A (en) * 2021-02-04 2021-06-11 吉林奥来德光电材料股份有限公司 Luminescent compound with organic condensed rings, preparation method thereof and organic electroluminescent device
WO2021131657A1 (en) * 2019-12-26 2021-07-01 出光興産株式会社 Compound, material for organic electroluminescent element, organic electroluminescent element and electronic device
CN113214237A (en) * 2021-05-15 2021-08-06 吉林奥来德光电材料股份有限公司 Organic electroluminescent material and preparation method and application thereof

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101087759A (en) * 2004-12-22 2007-12-12 出光兴产株式会社 Anthracene derivative and organic electroluminescent element using the same
JP2010027885A (en) * 2008-07-22 2010-02-04 Sony Corp Organic electroluminescent element
CN101675144A (en) * 2007-04-30 2010-03-17 Lg化学株式会社 Organic light emitting device and method of producing the same
CN101783396A (en) * 2009-01-19 2010-07-21 索尼公司 Organic electroluminescent element, display, and electronic apparatus
CN104835921A (en) * 2014-02-07 2015-08-12 罗门哈斯电子材料韩国有限公司 Organic electroluminescent device
CN105514288A (en) * 2014-10-13 2016-04-20 环球展览公司 Novel compounds and uses in devices
US20160190476A1 (en) * 2014-12-31 2016-06-30 Samsung Display Co., Ltd. Organic light-emitting device

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101087759A (en) * 2004-12-22 2007-12-12 出光兴产株式会社 Anthracene derivative and organic electroluminescent element using the same
CN101675144A (en) * 2007-04-30 2010-03-17 Lg化学株式会社 Organic light emitting device and method of producing the same
JP2010027885A (en) * 2008-07-22 2010-02-04 Sony Corp Organic electroluminescent element
CN101783396A (en) * 2009-01-19 2010-07-21 索尼公司 Organic electroluminescent element, display, and electronic apparatus
CN104835921A (en) * 2014-02-07 2015-08-12 罗门哈斯电子材料韩国有限公司 Organic electroluminescent device
CN105514288A (en) * 2014-10-13 2016-04-20 环球展览公司 Novel compounds and uses in devices
US20160190476A1 (en) * 2014-12-31 2016-06-30 Samsung Display Co., Ltd. Organic light-emitting device

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021131657A1 (en) * 2019-12-26 2021-07-01 出光興産株式会社 Compound, material for organic electroluminescent element, organic electroluminescent element and electronic device
CN114787137A (en) * 2019-12-26 2022-07-22 出光兴产株式会社 Compound, material for organic electroluminescent element, and electronic device
CN111440156A (en) * 2020-05-07 2020-07-24 吉林奥来德光电材料股份有限公司 Light-emitting auxiliary material, preparation method thereof and organic electroluminescent device
CN112939990A (en) * 2021-02-04 2021-06-11 吉林奥来德光电材料股份有限公司 Luminescent compound with organic condensed rings, preparation method thereof and organic electroluminescent device
CN112939990B (en) * 2021-02-04 2022-08-12 吉林奥来德光电材料股份有限公司 Luminescent compound with organic condensed rings, preparation method thereof and organic electroluminescent device
CN113214237A (en) * 2021-05-15 2021-08-06 吉林奥来德光电材料股份有限公司 Organic electroluminescent material and preparation method and application thereof
CN113214237B (en) * 2021-05-15 2022-05-24 吉林奥来德光电材料股份有限公司 Organic electroluminescent material and preparation method and application thereof

Similar Documents

Publication Publication Date Title
CN106699573B (en) Spiro organic material and organic electroluminescent device using the same
CN105492413B (en) Anthracene derivative and organic electroluminescent element using the same
KR101473019B1 (en) New compounds and organic electronic device using the same
CN110483495B (en) Heterocyclic compound and organic electroluminescent device thereof
KR20190078539A (en) Compound and organic light emitting device comprising the same
CN110845422A (en) Organic light-emitting compound, synthetic method thereof and organic electroluminescent device
CN108774258B (en) Boron-containing heterocyclic compound and application thereof in organic photoelectric device
CN111100072A (en) Organic photoelectric compound, synthetic method thereof and organic electroluminescent device
KR20110006915A (en) New compounds and organic electronic device using the same
CN111004201B (en) Organic electroluminescent compound, preparation method thereof and organic electroluminescent device
CN115417861B (en) Electron transport material, preparation method thereof, organic electroluminescent device comprising electron transport material and application of organic electroluminescent device
CN112375071B (en) Organic light-emitting compound and preparation method and application thereof
TW201300503A (en) Aromatic amine derivative and organic electroluminescent element using the same
CN110804053B (en) Electronic transmission material of imidazoazacycle and preparation method and application thereof
CN115745977A (en) Electron transport material, preparation method thereof and organic electroluminescent device
CN113620819A (en) Heteroatom-containing fused ring amine compound and application thereof
CN115304566A (en) Luminescent auxiliary material and preparation method and application thereof
CN109265399B (en) Compound and organic electroluminescent device
CN112457278B (en) Organic electroluminescent compound and preparation method and application thereof
EP2390249B1 (en) Novel cycloalkene derivatives and organic electronic devices using the same
CN111848687B (en) Red light organic electroluminescent material, preparation method thereof and photoelectric device
CN115368370A (en) Condensed nitrogen heterocyclic compound, application thereof and organic electroluminescent device containing compound
CN110845421A (en) Electron transport compound, synthesis method thereof and organic electroluminescent device
JP4721475B2 (en) Diindenopicene compound and organic light-emitting device using the same
CN116425724A (en) Organic electroluminescent compound and organic electroluminescent device

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
WW01 Invention patent application withdrawn after publication
WW01 Invention patent application withdrawn after publication

Application publication date: 20200228