WO2013182046A1 - 有机电子材料和有机电致发光器件 - Google Patents

有机电子材料和有机电致发光器件 Download PDF

Info

Publication number
WO2013182046A1
WO2013182046A1 PCT/CN2013/076758 CN2013076758W WO2013182046A1 WO 2013182046 A1 WO2013182046 A1 WO 2013182046A1 CN 2013076758 W CN2013076758 W CN 2013076758W WO 2013182046 A1 WO2013182046 A1 WO 2013182046A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
organic
electronic material
organic electronic
organic electroluminescent
Prior art date
Application number
PCT/CN2013/076758
Other languages
English (en)
French (fr)
Inventor
黄锦海
戴雷
陈金鑫
蔡丽菲
Original Assignee
广东阿格蕾雅光电材料有限公司
北京阿格蕾雅科技发展有限公司
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 广东阿格蕾雅光电材料有限公司, 北京阿格蕾雅科技发展有限公司 filed Critical 广东阿格蕾雅光电材料有限公司
Priority to US14/404,609 priority Critical patent/US10026901B2/en
Priority to KR1020147031329A priority patent/KR101781569B1/ko
Publication of WO2013182046A1 publication Critical patent/WO2013182046A1/zh

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
    • C07C13/66—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings the condensed ring system contains only four rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/72—Spiro hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • 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
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08—Radicals containing only hydrogen and carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • 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
    • C07D235/20—Two benzimidazolyl-2 radicals linked together directly or via a hydrocarbon or substituted hydrocarbon radical
    • 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
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/107—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with two aryl or substituted aryl radicals attached in positions 2 and 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D333/76—Dibenzothiophenes
    • 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
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5329—Polyphosphine oxides or thioxides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/008—Triarylamine dyes containing no other chromophores
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/008—Dyes containing a substituent, which contains a silicium atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • 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
    • H10K85/626—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
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/93—Spiro compounds
    • C07C2603/94—Spiro compounds containing "free" spiro atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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]
    • H10K50/14—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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron 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

Definitions

  • the invention relates to a novel organic electronic material, which is deposited into a thin film by vacuum evaporation, and is applied as an electron transporting material and a phosphorescent host material on an organic electroluminescent diode, and belongs to the field of organic electroluminescent device display technology.
  • organic electroluminescent devices have self-luminous, wide viewing angle, low power consumption, high efficiency, thin, rich color, fast response, wide temperature range, low driving voltage, flexible and bendable
  • the unique advantages of a transparent display panel and environmental friendliness make organic electroluminescent device technology suitable for use in flat panel displays and next-generation lighting, as well as backlights for LCDs.
  • Kodak’s Tang et al. used a vacuum thin film evaporation technique, using 8-hydroxyquinoline aluminum (Alq3) as the light-emitting layer, and a triphenylamine derivative as a hole transport layer to make a sandwich double-layer device at 10V.
  • a classic three-layer organic electroluminescent device comprises a hole transport layer, a light-emitting layer and an electron transport layer.
  • the electron transport layer of the device Alq 3 is traditionally used, has good film formation and thermal stability, but its strong green light and low electron mobility affect its industrial application.
  • some electron transport materials with superior properties such as TPBI, BCP, Bphen, etc. are also widely used in organic electroluminescent devices.
  • the existing luminescent layer materials can be basically divided into two types, namely fluorescent luminescent materials and phosphorescent luminescent materials, and the host-guest doping technology is often used.
  • CBP 4,4'-bis(9-carbazolyl)-biphenyl
  • CBP is a phosphorescent host material with high efficiency and high triplet energy level.
  • the triplet energy can be smoothly transferred to the phosphorescent material. This produces highly efficient red and green materials.
  • these representative host materials often limit their application due to their thermal stability and short lifetime of the fabricated devices.
  • organic electroluminescent devices have made great progress and development, and organic materials are constantly evolving. However, they meet market demands and have good device efficiency and longevity, and it is good There are still very few materials for performance and stability.
  • fluoranthene As an electroluminescent material, fluoranthene is widely used as an electron transport material, a hole transport material, and a luminescent material, but the reported literature either does not describe the device performance in detail, or the device efficiency is low and the device stability is low.
  • the present invention invents a series of novel compounds on the basis of fluoranthene and is applied to organic electroluminescent devices. Summary of the invention
  • the object of the present invention is to provide a high-performance organic electroluminescent device and a preparation method for a novel and novel organic electron transport and synthesis of a phosphorescent host material, and for use in a device.
  • the organic electronic material of the present invention has a chemical structural formula of the chemical formula (I) or the chemical formula (II):
  • Ri-R 5 Any four of Ri-R 5 are hydrogen, the other is a C1-C6 alkyl group, an aryl group of C7-C24, and one or more selected from N,
  • a substituted or unsubstituted heteroaryl ring group of S a triarylsilyl group, a diarylamino group, a diaryloxyphosphoryl group, an aromatic carbonyl group, an arylthio group;
  • R 3 and R 5 are hydrogen, and each independently is a C1-C6 alkyl group, a C6-C24 aryl group, a heteroaryl ring containing one or more selected g N, 0, S, a triarylsilyl group, and two Arylamino group, diaryloxyphosphoryl group, aromatic carbonyl group, arylthio group;
  • A is independently represented as C(R 6 ) 2 , N(R 7 ), S, 0, P( 8 ), S(0) 2 or B(R 9 ), - independently represented as hydrogen, deuterium, C1- C6 alkyl, phenyl, C1-C6 nonylphenyl, containing one or more heteroaryl selected from N, 0, S, or a cyclic structure formed between two R6 and C.
  • a fluorenyl group preferably a fluorenyl group, a C1-C4 fluorenyl group or a phenyl or naphthyl substituted five- or six-membered heteroaryl ring group, a diphenylamino group, a phenylnaphthylamino group, a triphenylsilyl group, two Phenylphosphine, phenylcarbonyl, phenylthio.
  • the five- or six-membered heterocyclic arene group is oxazolyl, pyrimidinyl, pyridyl, thiazolyl, triazolyl, triazinyl.
  • the fluorenyl group is 9,9-dimethylindenyl, 9,9-diphenylfluorenyl, 9,9-dimethylphenylindenyl or spirofluorenyl.
  • the R 2 and the hydrogen are hydrogen.
  • a preferably C(R 6 ) 2 , N(R 7 ), S, 0, S(0) 2 , -1 7 is preferably hydrogen, methyl, phenyl or methylphenyl, or two
  • a five-membered ring structure is formed between R « and C.
  • Preferred compounds of the invention are as follows, but are not limited to these
  • the organic electroluminescent device of the present invention comprises a substrate, an anode layer formed on the substrate, and a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer and a cathode anode are sequentially deposited on the anode layer.
  • the light emitting layer may be classified into a fluorescent light emitting layer or a phosphorescent light emitting layer.
  • One embodiment of the organic electroluminescent device of the present invention utilizes the compound of the present invention as an electron transporting material; another embodiment of the organic electroluminescent device of the present invention is that the above compound is used as a phosphorescent host material, and the guest material is preferably organic a ruthenium compound and an organoplatinum compound;
  • the above compound is used as a phosphorescent host material, and the above-described cooperation is used as an electron transport layer.
  • the organic electroluminescent device of the invention uses a fluoranthene group-containing compound as an electron transporting material, has high electron transporting and injecting ability, and also has good thermal stability and good film forming properties.
  • the organic electroluminescent device of the present invention uses a compound containing a fluoranthene group as a host material for phosphorescence, because it not only has a high The triplet energy level, and has good electron transport performance, can effectively increase the number of electrons in the light-emitting layer, and improve the efficiency of the device.
  • FIG. 1 is a structural view of a device of the present invention, wherein 10 represents a glass substrate, 20 represents an anode, 30 represents a hole injection layer, 40 represents a hole transport layer, 50 represents a light-emitting layer, and 60 represents an electron transport layer. 70 represents an electron injection layer and 80 represents a cathode.
  • Figure 2 is a 1 H NMR chart of Compound 46.
  • Figure 3 is a 1 H NMR chart of Compound 36.
  • Figure 4 is a DSC chart of compound 46.
  • the glass transition temperature of Compound 26 was tested by DSC method under a nitrogen atmosphere at a heating and cooling rate of 20 °C/min.
  • the measured compound 26 had a glass transition temperature Tg of 140 °C.
  • the glass transition temperatures of Compound 35, Compound 36, Compound 43, and Compound 46 were tested in the same manner, and the results are shown in Table 1.
  • the compound of the present invention has a higher glass transition temperature than conventional marketed host materials, and the present invention improves the thermal stability of the electroluminescent material.
  • the device structure is shown in FIG.
  • the transparent conductive ITO glass (the glass substrate 10 with the anode 20) was sequentially washed with a detergent solution and deionized water, ethanol, acetone, and deionized water. It was further treated with oxygen plasma for 30 seconds and then treated with plasma treated CF X. Then, a 5 nm thick MoO 3 hole injection layer 30 was evaporated on the ITO.
  • the TAPC was vaporized to form a 50 nm thick hole transport layer 40.
  • a 10 nm thick light-emitting layer 50 was vapor-deposited on the hole transporting layer, wherein compound 35 was a host light-emitting material and 10% FIrpic was used as a blue phosphorescent material.
  • TmPyPb 50 nm thick TmPyPb was vaporized on the light-emitting layer as the electron transport layer 60.
  • LiF 1.2 nm LiF was vaporized as an electron injection layer 70 and a 150 nm Al cathode.
  • the organic electroluminescent device prepared by the invention has a current density of 0.28 mA/cm 2 at a driving voltage of 4 V, and emits blue
  • the structure of the device was the same as in Example 7, except that CBP was used instead of Compound 35.
  • the organic electroluminescent device prepared in this comparative example had a current density of 0.17 mA/cm 2 at a driving voltage of 4 V and emitted blue light. Therefore, the present invention has a current density of Achilles tendon at the same driving voltage as compared with a conventional material, and the electroluminescence property is improved.

Abstract

本发明涉及"有机电致发光材料和有机电致发光器件"，具有如下式（I）或（II）所述的结构。本发明的有机电致发光器件采用了含有荧蒽基团的化合物作为电子传输材料，具有较高的电子传输和注入能力，也由于其具有很好的热稳定性和良好的成膜性能，在提高有机电致发光器件效率的同时，也提高了器件的使用寿命；同时，本发明的有机电致命发光器件采用了含有荧蒽基团的化合物作为磷光的主体材料，由于其不但具有较高的三线态能级，而且具有很好的电子传输性能，能有效的提高发光层中电子的数量，提高器件的效率。

Description

说明书 有机电子材料和有机电致发光器件 技术领域
本发明涉及新型的有机电子材料， 通过真空蒸渡沉积成薄膜， 作为电子传输材料和磷光 主体材料应用在有机电致发光二极管上， 属于有机电致发光器件显示技术领域。
技术背景
有机电致发光器件作为一种新型的显示技术， 具有自发光、 宽视角、 低能耗、 效率高、 薄、 色彩丰富、 响应速度快、 适用温度范围广、 低驱动电压、可制作柔性可弯曲与透明的显 示面板以及环境友好等独特优点， 因此，有机电致发光器件技术可以应用在平板显示器和新 一代照明上， 也可以作为 LCD的背光源。 自 1987年柯达公司的 Tang等利用真空薄膜蒸镀 技术， 用 8-羟基喹啉铝 （Alq3)作为发光层， 三苯胺衍生物作为空穴传输层做出的夹心式双 层器件，在 10V的驱动电压下，发光亮度达〖000 cd/m2 (Tang C. W., Vanslyke S. A. Appl. Phys. Lett. 1987, 51, 913-916)。这一突破性进展， 引起了科技界和产业界的广泛关注， 掀起了人们 对有机电致发光研究和应用的热潮。 随后， 于 1989年， 主客体技术的发明， 更是极大提高 了有机电致发光器件的发光效率和工作寿命。 1998年， Forrest等发现了电致磷光现象， 突 破了有机电致发光量子效率低于 25%的理论限制，提升到 100% (Baldo M. A., Forrest S. R. Et al, Nature, 1998, 395, 151-154), 使得有机电子发光的研究进入了一个新时期， 拓宽了其硏 究领域。
一个经典的三层有机电致发光器件包含有空穴传输层，发光层和电子传输层。其中器件 的电子传输层， 传统使用的是 Alq3， 具有良好的成膜性和热稳定性， 但是其发很强的绿光 和较低的电子迁移率， 影响了它的产业化应用。随后， 一些具有优越性能的电子传输材料如 TPBI, BCP, Bphen等也广泛应用在有机电致发光器件上。 而现有发光层材料基本可以分为 两类， 分别为荧光发光材料和磷光发光材料， 往往采用的是主客体掺杂技术。
CBP(4,4'-bis(9-carbazolyl)-biphenyl)是一个具有高效和高三线态能级的磷光主体材料，当 CBP 作为主体材料时，三线态能量能够顺利地转移到磷光发光材料，从而产生高效的红光和绿光 材料。但是这些具有代表性的主体材料，往往由于其的热稳定性和制备得到的器件寿命短而 限制它们的应用。
尽管经过 20年的发展， 有机电致发光器件已经取得了长足的进步和发展， 有机材料也 随之不断的发展进行中， 但是， 符合市场化需求的且具有良好的器件效率和寿命， 以及很好 性能和稳定性的材料还是很少。
荧蒽作为电致发光材料，应用广泛，可以作为电子传输材料，空穴传输材料，发光材料， 但是报道的文献要么没有详细描述器件性能， 要么器件的效率比较低以及较低的器件稳定 性， 本发明就是在荧蒽的基础上发明一系列新型化合物， 并且应用在有机电致发光器件上。 发明内容
本发明的目的是一种高效的新型有机电子传输和磷光主体材料的合成，以及在器件上的 应用， 提供高性能的有机电致发光器件和制备方法。
本发明所述的有机电子材料具有化学式 (I)或者化学式 (II) 的化学结构式：
Figure imgf000004_0001
(I ) (II )
其中，
Ri-R5中任意四个为氢，另一个为 C1-C6烷基、 C7-C24的芳基、含有一个或多个选自 N、
0、 S的取代或未取代的杂芳环基、 三芳香甲硅烷基、 二芳胺基、 二芳香氧磷基、 芳香羰基、 芳硫基； 或者
、 R3、 R5为氢， 、 分别独立为 C1-C6烷基、 C6-C24的芳基、 含有一个或多个选 g N、 0、 S的杂芳环、 三芳香甲硅烷基、 二芳胺基、 二芳香氧磷基、 芳香羰基、 芳硫基；
A独立地表示为 C(R6)2、 N(R7)、 S、 0、 P( 8), S(0)2或者 B(R9)， - 独立地表示为 氢、 氘、 C1-C6烷基、 苯基、 C1-C6垸基苯基、 含有一个或多个选自 N、 0、 S的杂芳基， 或两个 R6与 C之间形成环状结构。
优选， - 优选为芴基、 C1-C4垸基或苯基或萘基取代的五元或六元杂芳环基、 二苯 基胺基、 苯萘胺基、 三苯基甲硅烷基、 二苯基氧磷、 苯基羰基、 苯基硫基。
其中所述五元或六元杂环芳烃基为咔唑基、 嘧啶基、 吡啶基、 噻唑基， 三氮唑基， 三嗪 基。
所述芴基为 9， 9-二甲基芴基、 9， 9-二苯基芴基、 9， 9-二甲苯基芴基或螺芴基。 所述 、 R2、 、 为氢。 A优选 C(R6)2、 N(R7)、 S、 0、 S(0)2， -1 7优选氢、 甲基， 苯基或甲基苯基， 或两个
R«与 C之间形成五元环状结构。
本发明优选的化合物如下， 但是并没有限制在这些里面
Figure imgf000005_0001
10
11 12
Figure imgf000006_0001
S.9.0/CT0ZN3/X3d 9l70Z8l/ClOZ OAV
Figure imgf000007_0001
S.9.0/CT0ZN3/X3d 9l70Z8l/ClOZ OAV
Figure imgf000008_0001
更优选:
Figure imgf000008_0002
Figure imgf000009_0001
本发明的有机电致发光器件包括基板，于基板上形成的阳极层，于阳极层上依次蒸镀空 穴注入层， 空穴传输层， 发光层， 电子传输层以及电子注入层和阴极阳极。
发光层可分为荧光发光层或者为磷光发光层。
本发明中的有机电子发光器件一个实施方式， 利用本发明的化合物作为电子传输材料； 本发明的有机电致发光器件的另外一个实施方式为， 利用以上化合物作为磷光主体材 料， 客体材料优选为有机铱化合物和有机铂化合物；
本发明的有机电致发光器件中，利用以上化合物作为磷光主体材料，并利用以上化合作 为电子传输层。 本发明的有机电致发光器件釆用了含有荧蒽基团的化合物作为电子传输材料，具有较高 的电子传输和注入能力，也由于其具有很好的热稳定性和良好的成膜性能，在提高有机电致 发光器件效率的同时， 也提高了器件的使用寿命； 同时， 本发明的有机电致命发光器件采用 了含有荧蒽基团的化合物作为磷光的主体材料， 由于其不但具有较高的三线态能级，而且具 有很好的电子传输性能， 能有效的提高发光层中电子的数量， 提高器件的效率。
附图说明
图 1为本发明的器件结构图， 其中 10代表为玻璃基板， 20代表为阳极， 30代表为空穴注入 层， 40代表为空穴传输层， 50代表为发光层， 60代表为电子传输层， 70代表为电子注入层， 80代表为阴极。 图 2 为化合物 46的 1H NMR图。
图 3 为化合物 36的 1H NMR图。
图 4 为化合物 46的 DSC图。
具体实施方式
下面结合实施例对本发明作进一步的详细说明。
实施例 1 : 化合物 43合成
Figure imgf000010_0001
中间体 1-1的合成
向烧瓶中加入 7.5 g 2-溴 -9,9-二甲基省， 0.15 g碘化亚铜， 0.3 g 四三苯基磷钯， 然后加 入三乙胺通氮气， 开始搅拌， 使充分溶解， 然后加入 10 ml三甲基硅乙炔， 过夜回流反应 12小时。 减压除去溶剂。 加入水， 用乙醚萃取三次， 合并有机相， 用饱和食盐水洗三次， 干燥， 抽滤， 浓缩， 得到 6.8 g产品， 产率 85%。 中间体 1-2的合成
向烧瓶中加入 45 ml 甲醇， 50 ml 二氯甲烷， 5 g氢氧化钾， 6.8 g 中间体 1-1， 通氮气， 搅拌反应 1小时。 过滤除去无机盐， 除去有机溶剂， 滤饼用甲醇重结晶， 得到 4.2 g， 产率 为 82%。 中间体 1-3的合成
将 84 g苊醌， 72.8 gl，3-二苯基丙酮， 600ml乙醇， 56g氢氧化钾， 加入四口烧瓶， 开始 搅拌， 通氮气， 回流 2小时。 冷却室温， 过滤， 滤饼用乙醇淋洗 2次， 得到 130 g黑色固体， 产率为 91%。 化合物 43的合成
将 4.2 g 中间体 1-2和 6.3g中间体 1-3， 还 60 ml二苯醚加入到四口烧瓶中， 开始搅拌， 通氮气 10分钟， 开始加热回流 12小时， 冷却， 过滤， 滤饼用乙酸乙酯加热回流， 冷却， 过 滤得到 6.5 g淡黄色固体， 产率为 66%。 NMR (400 MHz, CD2C12, δ): 7.56-7.74 (m, 9 H), 7.21-7.44 (m, 14 H), 7.76-7.70 (m, 1 H), 1.27 (s, 6 H). MALDI-TOF-MS m/s 计算值 C43H30 : 546.2， 实测值 [M+]: 546.5。 2: 化 46合成
Figure imgf000011_0001
中间体 2-1的合成
向烧瓶中加入 8.0 g 中间体 2-0， 0.15 g碘化亚铜， 0.3 g 四三苯基磷钯， 然后加入三乙 胺通氮气， 开始搅拌， 使充分溶解， 然后加入 L0 ml三甲基硅乙炔， 过夜回流反应 12小时。 减压除去溶剂。加入水，用乙醚萃取三次， 合并有机相， 用饱和食盐水洗三次， 干燥， 抽滤， 浓缩， 得到 6.8g产品， 产率 83%。 中间体 2-2的合成
向烧瓶中加入 45 ml 甲醇， 50 ml二氯甲烷， 5g氢氧化钾， 7 g 中间体 2-1， 通氮气， 搅拌反应 1小时。 过滤除去无机盐， 除去有机溶剂， 滤饼用甲醇重结晶， 得到 4.0 g， 产率 为 70%。 化合物 46的合成
将 4.0 g 中间体 2-2和 4.2 g中间体 1-3， 60 ml二苯醚加入到四口烧瓶中， 开始搅拌， 通氮气 10分钟， 开始加热回流 12小时， 冷却， 过滤， 滤饼用乙酸乙酯加热回流， 冷却， 过 滤得到 7.0 g淡黄色固体， 产率为 89%。 ^ NMR (400 MHz, CDC13, δ) : 7.61-7,79 (m,8 Η), 7.47-7.52 (m, 3 Η), 7.32-7.36 (m, 5 Η), 7.20-7.24 (m, 3 Η), 7.02-7.14〔m, 8 Η), 6.56-6.65 (m, 4 Η〕， 6.49 (s, 1 Η)。如图 2。 MALDI-TOF-MS m/s 计算值 C53H32 : 668.3 , 实测值 [M+]: 668.5。 实施例 3 ： 化合物 35合成
Figure imgf000012_0001
35 中间体 3-1的合成
向烧瓶中加入 7.7 g 中间体 3-0， 0.15 g碘化亚铜， 0.3 g 四三苯基磷钯， 然后加入三乙 胺通氮气， 开始搅拌， 使充分溶解， 然后加入 L0 ml三甲基硅乙炔， 过夜回流反应 12小时。 减压除去溶剂。加入水，用乙醚萃取三次， 合并有机相， 用饱和食盐水洗三次， 干燥， 抽滤， 浓缩， 得到 6.8g产品， 产率 67%。 中间体 3-2的合成
向烧瓶中加入 45 ml 甲醇， 50 ml 二氯甲烷， 5g氢氧化钾， 5.5 g 中间体 3-1， 通氮气， 搅拌反应 1小时。 过滤除去无机盐， 除去有机溶剂， 滤饼用甲醇重结晶， 得到 4.11 g， 产率 为 95%。 化合物 35的合成
将 4.0 g 中间体 3-2和 5.5 g中间体 1-3 , 60 ml二苯醚加入到四口烧瓶中， 开始搅拌， 通氮气 10分钟， 开始加热回流 12小时， 冷却， 过滤， 滤饼用乙酸乙酯加热回流， 冷却， 过 滤得到 4.5 g淡黄色固体，产率为 49% ^ NMR (400 MHz, CD2C12, 5)： 8.12-8.13 (d, J = 7.6 Hz, 2 H), 7.74-7.77 (m, 4 H), 7.52-7.60 (m, 3 H), 7.25-7.45 (m, 19 H), 6.69-6.81 (d, J=7.2 Hz, 1 H). MALDI-TOF-MS m/s 计算值 C46H29N: 595.2, 实测值 [M+] : 595.4。 实施例 4 ： 化合物 26合成
Figure imgf000014_0001
Figure imgf000014_0002
实施例 5 ： 化合物 36合成
Figure imgf000015_0001
中间体 5-1的合成
向烧瓶中加入 9.1 g化合物 5-0， 0.15 g碘化亚铜， 0.24 g 四三苯基磷钯， 然后加入 100 ml三乙胺通氮气， 开始搅拌， 使充分溶解， 然后加入 10 ml三甲基硅乙炔， 过夜回流反应 12小吋。 减压除去溶剂。 加入水， 用乙醚萃取三次， 合并有机相， 用饱和食盐水洗三次， 干燥， 抽滤， 浓缩， 得到 6.8 g产品， 产率 74%。 中间体 5-2的合成
向烧瓶中加入 45 ml 甲醇， 50 ml二氯甲烷， 5 g氢氧化钾， Ί g 中间体 2- 1， 通氮气， 搅拌反应 1小时。 过滤除去无机盐， 除去有机溶剂， 滤饼用甲醇重结晶， 得到 5.0 g， 产率 为 83%。 化合物 36的合成
将 4.8 g 中间体 6-2和 3.9 g中间体 1-3 , 60 ml二苯醚加入到四口烧瓶中， 开始搅拌， 通氮气 10分钟， 开始加热回流 12小时， 冷却， 过滤, 1滤饼用乙酸乙酯加热回流， 冷却， 过 滤得到 5.5 g淡黄色固体，产率为 65%。 NMR (400 MHz, CD2C12, δ): 8.14-8.16 (d, J =8.4 Hz, 4 H), 7.72-7.80 (m, 4 H), 7.54-7.69 (m, 11 H), 7.27-7.50 (m, 16 H), 6.74-6.76 (d, J = 6.8 Hz, 1H). 如图 3。 MALDI-TOF-MS m/s 计算值 C59H36N2: 760.3， 实测值 [M+] : 760.5。 实施例 6
在氮气保护下， 以 20°C/min的加热和冷却速度用 DSC方法测试化合物 26的玻璃化温度。 测得的化合物 26的玻璃化转变温度 Tg为 140°C。用相同的方法测试化合物 35， 化合物 36， 化合物 43,和化合物 46的玻璃化温度， 所得结果列于表 1中。
比较例 1
跟实施例 1一样的条件， 测得化合物 mCP和 BCP的玻璃化转变温度， 所得结果也列于表 1 。
Figure imgf000016_0001
Figure imgf000016_0002
从表 1中， 可以看出本发明的化合物比常规的市场化的主体材料具有更高的玻璃化转变温 度， 本发明改善了电致发光材料的热稳定性。 实施 7 使用本发明的有机电致发光材料制备 OLED, 器件结构如图 1 首先，将透明导电 ITO玻璃（带有阳极 20的玻璃基板 10)依次经:洗涤剂溶液和去离子水， 乙醇， 丙酮， 去离子水洗净。 再用氧等离子处理 30秒， 接着用等离子处理的 CFX处理。 然后， 在 ITO上蒸渡 5 nm厚的 Mo03空穴注入层 30。
然后， 蒸渡 TAPC形成 50 nm厚的空穴传输层 40。
然后， 在空穴传输层上蒸渡 10 nm厚发光层 50， 其中， 化合物 35为主体发光材料， 而以 10%FIrpic作为作为蓝色磷光材料。
然后， 在发光层上蒸渡 50 nm厚的 TmPyPb作为电子传输层 60。
最后， 蒸渡 1.2 nm LiF作为电子注入层 70和 150 nm Al阴极。
本发明所制备的有机电致发光器件在 4V的驱动电压下的电流密度为 0.28 mA/cm2, 发 射蓝
Figure imgf000017_0001
比较例 2
器件结构跟实施例 7—样， 除了用 CBP代替化合物 35。
此比较例制备的有机电致发光器件在 4V的驱动电压下的电流密度为 0.17 mA/cm2，发射 蓝光。 因此， 本发明相比较常规的材料， 在相同的驱动电压下具有跟髙的电流密度， 改善了 电致发光性质。

Claims

权利要求书
1、 一种有机电子材料， 具有如下式 （I) 或（II) 所述的结构，
Figure imgf000018_0001
(I) (II)
其中，
Rr 中任意四个为氢，另一个为 C1-C6烷基、 C7-C24的芳基、含有一个或多个选自 N、 0、 S的取代或未取代的杂芳环、 三芳香甲硅垸基、 二芳胺基、 二芳香氧磷基、 芳香羰基、 芳硫基； 或者
R3、 为氢， 、 分别独立为 C1-C6烷基、 C6-C24的芳基、 含有一个或多个选 自 N、 0、 S的杂芳环、 三芳香甲硅烷基、 二芳胺基、 二芳香氧磷基、 芳香羰基、 芳硫基； A独立地表示为 C(R6)2、 N(R7)、 S、 0、 P(R8)、 S(0)2或者 B(R9)， R6-R9独立地表示为 氢、 氘、 烷基、 苯基、 烷基苯基、 含有一个或多个选自 N、 0、 S的杂芳基， 或两个 R6与 C 之间形成环状结构。
2、 根据权利要求 1所述的有机电子材料， 其中 RrR5中任意四个为氢， 另一个为芴基、 垸 基或苯基或萘基取代的五元或六元杂芳环基、 二苯基胺基、苯萘胺基、三苯基甲硅烷基、二 苯基氧磷、 苯基羰基或苯基硫基。
3、根据权利要求 2所述的有机电子材料， 其中所述五元或六元杂芳环基为咔唑基、嘧啶基、 吡啶基、 噻唑基、 三氮唑基或三嗪基。
4、 根据权利要求 2所述的有机电子材料， 其中所述芴基为 9， 9-二甲基芴基、 9, 9-二苯基 芴基、 9， 9-二甲苯基芴基或螺芴基。
5、 根据权利要求 2-4任一所述的有机电子材料， 其中 、 R2、 、 R5为氢。
6、根据权利要求 1所述的有机电致发光材料， 其中 A为 C(R6)2、 N(R7)、 S、 0、 S(0)2， R6、
R7独立为氢、 甲基、 苯基或甲基苯基， 或两个 R6与 C之间形成五元环状结构。 、 权利要求 1所述的有机电子材料， 其结构如下:
Figure imgf000019_0001
Figure imgf000020_0001
81·
S.9.0/CT0ZN3/X3d 9^0Ζ8ΐ/εΐΟΖ OAV
Figure imgf000021_0001
61·
S.9.0/CT0ZN3/X3d 9^0Ζ8ΐ/εΐΟΖ OAV
Figure imgf000022_0001
、 权利要求 1所述的有机电子材料， 其结构式为:
Figure imgf000022_0002
Figure imgf000023_0001
9、 一种含有权利要求 1-8任一所述的有机电子材料的有机电致发光器件。
10、 根据权利要求 9所述的有机电致发光器件， 包括空穴注入层， 空穴传输层， 发光层， 电 子传输层或 /和电子注入层， 其中权利要求 1-8任一所述的有机电子材料作为空穴注入层， 空穴传输层， 发光层， 电子传输层或 /和电子注入层中的任一层或多层中的材料。
11、 根据权利要求 10所述的有机电致发光器件， 权利要求 1-8任一所述的有机电子材料作 为电子传输层的材料。
12、 根据权利要求 10所述的有机电致发光器件， 所述发光层中包括主体材料和客体材料， 其中权利要求 1-8任一所述的有机电子材料为发光层中红色磷光的主体材料。
13、 根据权利要求 12所述的有机电致发光器件， 其中客体材料为有机铱化合物或有机铂化 合物。
14、根据权利要求 12或 13所述的有机电致发光器件， 权利要求 1-S任一所述的有机电子材 料作为电子传输层的材料。
PCT/CN2013/076758 2012-06-06 2013-06-05 有机电子材料和有机电致发光器件 WO2013182046A1 (zh)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US14/404,609 US10026901B2 (en) 2012-06-06 2013-06-05 Organic electronic material and organic electroluminescent device
KR1020147031329A KR101781569B1 (ko) 2012-06-06 2013-06-05 유기 전자재료와 유기전기 발광소자

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201210185154 2012-06-06
CN201210185154.3 2012-06-06

Publications (1)

Publication Number Publication Date
WO2013182046A1 true WO2013182046A1 (zh) 2013-12-12

Family

ID=49711373

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2013/076758 WO2013182046A1 (zh) 2012-06-06 2013-06-05 有机电子材料和有机电致发光器件

Country Status (6)

Country Link
US (1) US10026901B2 (zh)
KR (1) KR101781569B1 (zh)
CN (1) CN103468243B (zh)
HK (1) HK1191041A1 (zh)
TW (1) TWI510597B (zh)
WO (1) WO2013182046A1 (zh)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015050173A1 (ja) * 2013-10-03 2015-04-09 出光興産株式会社 化合物、有機エレクトロルミネッセンス素子及び電子機器
EP2860782A1 (en) * 2013-10-09 2015-04-15 Novaled GmbH Semiconducting material comprising a phosphine oxide matrix and metal salt
EP2933852A1 (en) * 2014-04-17 2015-10-21 Novaled GmbH Phosphorescent OLED and hole transporting materials for phosphorescent OLEDs
WO2016002921A1 (ja) * 2014-07-03 2016-01-07 東ソー株式会社 環状アジン化合物、その製造方法、及びその用途
JP2016505507A (ja) * 2012-11-21 2016-02-25 エルジー・ケム・リミテッド フルオランテン化合物およびそれを含む有機電子素子
KR20170013236A (ko) 2014-05-28 2017-02-06 도레이 카부시키가이샤 플루오란텐 유도체, 그것을 함유하는 전자 디바이스, 발광 소자 및 광전 변환 소자
JPWO2015115530A1 (ja) * 2014-01-31 2017-03-23 出光興産株式会社 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器
CN107586295A (zh) * 2016-07-08 2018-01-16 广东阿格蕾雅光电材料有限公司 高Tg有机电子传输材料
JP2018172319A (ja) * 2017-03-31 2018-11-08 出光興産株式会社 新規な化合物、有機エレクトロルミネッセンス素子、電子機器

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104037340B (zh) * 2014-06-25 2017-01-25 上海道亦化工科技有限公司 一种有机电致发光器件
KR101745799B1 (ko) * 2014-12-24 2017-06-09 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
US11355714B2 (en) * 2015-10-27 2022-06-07 Merck Patent Gmbh Materials for organic electroluminescent devices
CN106356452B (zh) * 2015-12-09 2018-09-18 广东阿格蕾雅光电材料有限公司 仅电子有机半导体二极管器件
CN106542957B (zh) * 2015-12-09 2019-05-14 广东阿格蕾雅光电材料有限公司 有机电子传输材料
CN107586294B (zh) * 2016-07-08 2019-10-18 广东阿格蕾雅光电材料有限公司 高Tg有机电子传输器件
CN107778260A (zh) * 2016-08-24 2018-03-09 株式会社Lg化学 新型有机发光材料及包含其的有机发光元件
TWI756292B (zh) * 2016-11-14 2022-03-01 德商麥克專利有限公司 具有受體基團與供體基團之化合物
CN109755416B (zh) * 2017-11-02 2019-12-20 广东阿格蕾雅光电材料有限公司 含咔唑及吡啶构建单元材料的有机电致发光器件
TW202122558A (zh) * 2019-09-03 2021-06-16 德商麥克專利有限公司 用於有機電致發光裝置之材料
KR102455718B1 (ko) * 2020-07-10 2022-10-17 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
CN112961141A (zh) * 2021-02-08 2021-06-15 北京燕化集联光电技术有限公司 一种有机材料及其应用
CN113278003B (zh) * 2021-05-25 2022-07-15 烟台九目化学股份有限公司 一种以氘代蒽螺芴环内醚为主体的材料及应用

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080071122A1 (en) * 2006-09-15 2008-03-20 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and material for organic electroluminescence device
WO2009008352A1 (ja) * 2007-07-07 2009-01-15 Idemitsu Kosan Co., Ltd. 有機ｅｌ素子
WO2009008348A1 (ja) * 2007-07-07 2009-01-15 Idemitsu Kosan Co., Ltd. 有機ｅｌ素子
CN101730947A (zh) * 2007-07-07 2010-06-09 出光兴产株式会社 有机el元件及含有有机el材料的溶液
KR20110137897A (ko) * 2010-06-18 2011-12-26 주식회사 알파켐 플루오란센 유도체 및 이를 이용한 유기전계발광소자

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1817064B (zh) * 2003-07-02 2010-12-01 松下电器产业株式会社 发光元件以及显示装置
DE10345583A1 (de) * 2003-09-29 2005-05-19 Basf Ag Synthese von phenylsubstituierten Fluoranthenen durch Diels-Alder-Reaktion und ihre Verwendung
CN101432251A (zh) * 2006-04-27 2009-05-13 佳能株式会社 4-芳基芴化合物和使用该化合物的有机发光器件
JP4818159B2 (ja) * 2006-04-27 2011-11-16 キヤノン株式会社 フルオランテン誘導体およびそれを有する有機発光素子
JP2008231052A (ja) * 2007-03-22 2008-10-02 Shinshu Univ フルオレン−フルオランテン化合物及びそれを用いた有機電界発光素子
US8076009B2 (en) * 2007-10-26 2011-12-13 Global Oled Technology, Llc. OLED device with fluoranthene electron transport materials
US8129039B2 (en) * 2007-10-26 2012-03-06 Global Oled Technology, Llc Phosphorescent OLED device with certain fluoranthene host
JP2009130141A (ja) * 2007-11-22 2009-06-11 Idemitsu Kosan Co Ltd 有機ｅｌ素子および有機ｅｌ材料含有溶液

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080071122A1 (en) * 2006-09-15 2008-03-20 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and material for organic electroluminescence device
WO2009008352A1 (ja) * 2007-07-07 2009-01-15 Idemitsu Kosan Co., Ltd. 有機ｅｌ素子
WO2009008348A1 (ja) * 2007-07-07 2009-01-15 Idemitsu Kosan Co., Ltd. 有機ｅｌ素子
CN101730947A (zh) * 2007-07-07 2010-06-09 出光兴产株式会社 有机el元件及含有有机el材料的溶液
KR20110137897A (ko) * 2010-06-18 2011-12-26 주식회사 알파켐 플루오란센 유도체 및 이를 이용한 유기전계발광소자

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
BHATTACHARYA, S. ET AL.: "Electronic structures and ionicity in [60]fullerencipolycyclic aromatic hydrocarbon charge transfer complexes studied by UV-Vis and NMR.", JOURNAL OF MOLECULAR STRUCTURE., vol. 784, no. 1-3, 2006, pages 124 - 137 *
KIM, S.K. ET AL.: "Substituent effect of fluoranthene derivatives in electroluminescence.", MOL. CRYST. LIQ. CRYST., vol. 498, 2009 *
TONG, QINGXIAO ET AL.: "A High performance nondoped blue organic lLight-emitting device based on a diphenylfluoranthene-sSubstituted fluorene derivative.", JOURNAL OF PHYSICAL CHEMISTRY C., vol. 113, no. 15, 2009, pages 6227 - 6230 *
TONG, QINGXIAO ET AL.: "Efficient green organic light-Emitting devices with a nondoped dual-functional electroluminescent material.", APPLIED PHYSICS LETTERS, vol. 91, no. 15, 2007 *
TONG, QINGXIAO ET AL.: "High-efficiency undoped blue organic light-emitting device.", DYES AND PIGMENTS., vol. 86, no. 3, 2010, pages 233 - 237 *

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10680182B2 (en) 2012-11-21 2020-06-09 Lg Chem, Ltd. Fluoranthene compound, and organic electronic device comprising same
JP2016505507A (ja) * 2012-11-21 2016-02-25 エルジー・ケム・リミテッド フルオランテン化合物およびそれを含む有機電子素子
EP2924020A4 (en) * 2012-11-21 2016-06-15 Lg Chemical Ltd FLUORANTHENE COMPOUND AND ORGANIC ELECTRONIC DEVICE COMPRISING THE SAME
WO2015050173A1 (ja) * 2013-10-03 2015-04-09 出光興産株式会社 化合物、有機エレクトロルミネッセンス素子及び電子機器
US10622569B2 (en) 2013-10-03 2020-04-14 Idemitsu Kosan Co., Ltd. Compound, organic electroluminescent element, and electronic device
EP2860782A1 (en) * 2013-10-09 2015-04-15 Novaled GmbH Semiconducting material comprising a phosphine oxide matrix and metal salt
WO2015052284A1 (en) * 2013-10-09 2015-04-16 Novaled Gmbh Semiconducting material comprising a phosphine oxide matrix and metal salt
JP2016534546A (ja) * 2013-10-09 2016-11-04 ノヴァレッド ゲーエムベーハー ホスフィンオキシドマトリックス及び金属塩を含む半導体材料
JPWO2015115530A1 (ja) * 2014-01-31 2017-03-23 出光興産株式会社 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子及び電子機器
US10297757B2 (en) 2014-01-31 2019-05-21 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element and electronic device
WO2015158886A1 (en) * 2014-04-17 2015-10-22 Novaled Gmbh Phosphorescent oled and hole transporting materials for phosphorescent oleds
EP2933852A1 (en) * 2014-04-17 2015-10-21 Novaled GmbH Phosphorescent OLED and hole transporting materials for phosphorescent OLEDs
KR20170013236A (ko) 2014-05-28 2017-02-06 도레이 카부시키가이샤 플루오란텐 유도체, 그것을 함유하는 전자 디바이스, 발광 소자 및 광전 변환 소자
WO2016002921A1 (ja) * 2014-07-03 2016-01-07 東ソー株式会社 環状アジン化合物、その製造方法、及びその用途
CN107586295A (zh) * 2016-07-08 2018-01-16 广东阿格蕾雅光电材料有限公司 高Tg有机电子传输材料
CN107586295B (zh) * 2016-07-08 2019-11-22 广东阿格蕾雅光电材料有限公司 高Tg有机电子传输材料
JP2018172319A (ja) * 2017-03-31 2018-11-08 出光興産株式会社 新規な化合物、有機エレクトロルミネッセンス素子、電子機器

Also Published As

Publication number Publication date
US20150108449A1 (en) 2015-04-23
TW201404862A (zh) 2014-02-01
CN103468243B (zh) 2015-08-19
KR20150011348A (ko) 2015-01-30
TWI510597B (zh) 2015-12-01
CN103468243A (zh) 2013-12-25
US10026901B2 (en) 2018-07-17
KR101781569B1 (ko) 2017-09-26
HK1191041A1 (zh) 2014-07-18

Similar Documents

Publication Publication Date Title
TWI510597B (zh) Organic electronic materials and organic electroluminescent devices
JP5364089B2 (ja) 正孔輸送ユニットと電子輸送ユニットとを含む有機光電素子用材料及びこれを含む有機光電素子
EP2215183B1 (en) New compound and organic light emitting device using the same
TWI495625B (zh) Organic electroluminescent devices
TWI593684B (zh) 有機電致發光材料和有機電致發光器件
TWI570984B (zh) Organic electronic materials
CN110305149B (zh) 一种热激活延迟荧光材料及其应用
JP7458483B2 (ja) 金属錯体及びその用途
TWI641598B (zh) 化合物及其有機電子裝置
WO2022242521A1 (zh) 一种稠合氮杂环化合物及其应用以及包含该化合物的有机电致发光器件
JP5378397B2 (ja) 高効率の青色電界発光化合物およびこれを使用する表示素子
KR20110057008A (ko) 신규한 디아민 유도체, 이의 제조방법 및 이를 이용한 유기 전자 소자
CN111454251A (zh) 一种吡嗪衍生物及其在oled器件中的应用
JP7402979B2 (ja) 白金金属錯体及び有機エレクトロルミネセンスデバイスにおけるその用途
TWI612047B (zh) 有機電子傳輸材料
CN111393458B (zh) 一种杂环化合物及其有机电致发光器件
CN114644637A (zh) 三（1,2-苯基）二胺衍生物有机光电材料及其应用
CN115873025A (zh) 一种稠合杂环类化合物及其应用以及包含该化合物的有机电致发光器件
CN111187254A (zh) 一种基于咔唑的有机电致磷光材料组成物及其应用
CN111205269B (zh) 基于咔唑的有机电致磷光材料组成物制备方法及应用制备
CN114507224B (zh) 一种含酮的有机化合物及其应用
CN109599504A (zh) 一种新型化合物及采用该化合物的有机电致发光器件
KR20160013239A (ko) 유기 전계 발광 소자
CN114220926A (zh) 一种高效长寿命的蓝光有机电致发光器件
CN114805265A (zh) 一种基于菲和蒽的蓝光主体材料及其在有机电致发光器件上的应用

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 13800882

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 20147031329

Country of ref document: KR

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: 14404609

Country of ref document: US

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 13800882

Country of ref document: EP

Kind code of ref document: A1