CN110003090A - 茚衍生物、含有茚衍生物的有机电致发光器件 - Google Patents

茚衍生物、含有茚衍生物的有机电致发光器件 Download PDF

Info

Publication number
CN110003090A
CN110003090A CN201910260776.XA CN201910260776A CN110003090A CN 110003090 A CN110003090 A CN 110003090A CN 201910260776 A CN201910260776 A CN 201910260776A CN 110003090 A CN110003090 A CN 110003090A
Authority
CN
China
Prior art keywords
base
group
aryl
optionally
substituent group
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.)
Granted
Application number
CN201910260776.XA
Other languages
English (en)
Other versions
CN110003090B (zh
Inventor
曹建华
隋岩
董梁
温世文
唐永顺
邢玉彬
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.)
Shijiazhuang Chengzhi Yonghua Display Material Co Ltd
Original Assignee
Beijing Chengzhi Yonghua Display Technology Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Beijing Chengzhi Yonghua Display Technology Co Ltd filed Critical Beijing Chengzhi Yonghua Display Technology Co Ltd
Priority to CN201910260776.XA priority Critical patent/CN110003090B/zh
Publication of CN110003090A publication Critical patent/CN110003090A/zh
Application granted granted Critical
Publication of CN110003090B publication Critical patent/CN110003090B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
    • C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
    • C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D213/60—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 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • 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
    • 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
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/46—Phenazines
    • 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
    • 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
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other 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
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • 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
    • C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02—Polyamines
    • C08G73/026—Wholly aromatic polyamines
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • 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
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/24—Anthracenes; Hydrogenated anthracenes
    • 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
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • 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
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/50—Pyrenes; Hydrogenated pyrenes
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/12—Copolymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/10—Definition of the polymer structure
    • C08G2261/14—Side-groups
    • C08G2261/148—Side-chains having aromatic units
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/314—Condensed aromatic systems, e.g. perylene, anthracene or pyrene
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/31—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain
    • C08G2261/316—Monomer units or repeat units incorporating structural elements in the main chain incorporating aromatic structural elements in the main chain bridged by heteroatoms, e.g. N, P, Si or B
    • C08G2261/3162—Arylamines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
    • 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
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1416—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
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1425—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
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

本发明公开了一种茚衍生物、包含所述茚衍生物的有机电致发光器件。本发明的茚衍生物具有较大的空间位阻和载流子迁移率，利用本发明的材料制备的有机电致发光器件可明显降低驱动电压、提高发光效率和亮度。

Description

茚衍生物、含有茚衍生物的有机电致发光器件
技术领域
本发明涉及有机电致发光材料技术领域。更具体地，涉及用于有机电致发光的材料和有机电致发光器件。
背景技术
有机电致发光(简称OLED)及相关的研究早在1963年pope等人首先发现了有机化合物单晶蒽的电致发光现象。1987年美国的柯达公司用蒸镀有机小分子的方法制成了一种非晶膜型器件，将驱动电压降到了20V以内。这类器件由于具有超轻薄、全固化、自发光、亮度高、视角宽、响应速度快、驱动电压低、功耗小、色彩鲜艳、对比度高、工艺过程简单、温度特性好、可实现柔软显示等优点，可广泛应用于平板显示器和面光源，因此得到了广泛地研究、开发和使用。
经过二十几年的发展，有机EL材料已经全面实现了红、蓝、绿色发光，应用领域也从小分子扩展到了高分子以及金属络合物等领域。最近几年有机电发光显示技术己趋于成熟，一些产品已进入市场，但在产业化时程中，仍有许多问题亟待解决，特别是用于制作器件的各种有机材料，其载流子注入、传输性能，材料电发光性能、使用寿命、色纯度、各种材料之间及与各电极之间的匹配等，尚有许多问题还未解决。
因此，需要提供一种提高电子迁移率，降低驱动电压，提高器件的亮度和效率的材料，至少解决上述之一的问题。
发明内容
为了克服现有技术存在的问题，本发明人等进行了深入研究，目的在于提供一种茚衍生物，其具有较大的空间位阻和载流子迁移率，从而，利用该茚衍生物制备得到的有机电致发光材料能够明显降低驱动电压、提高发光效率和亮度。
为达到上述目的，本发明采用下述技术方案：
一种茚衍生物，其结构式如式I所示：
其中，R1表示氢原子、氘原子、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、C1-C20链烷基、C3-C20环烷基、C2-C20烯基、C2-C20炔基、C1-C20烷氧基、C3-C20环烷烃基、C4-C20环烯烃基、C1-C20杂烷基、任选具有取代基的C6-C60芳基、任选具有取代基的C6-C60芳香乙烯基、任选具有取代基的C6-C60稠环芳香基、任选具有取代基的C6-C60芳胺基、任选具有取代基的C6-C60含氮原子的稠环芳基、任选具有取代基的C6-C60含硫或氧原子的稠环芳基、任选具有取代基的C6-C60含磷、硅或硼原子的稠环芳基、或任选具有取代基的C3-C60杂环芳基；
Ar1、Ar2各自独立地选自任选具有取代基的C6-C60芳基、任选具有取代基的C6-C60含氧芳基、任选具有取代基的C6-C60含硫芳基、任选具有取代基的C6-C60含磷芳基、任选具有取代基的C6-C60含氮芳基、任选具有取代基的C6-C60含硅芳基、任选具有取代基的C6-C60含硼芳基、任选具有取代基的C6-C60稠环芳香基、任选具有取代基的C6-C60芳胺基、任选具有取代基的C3-C60杂环芳基组成的组，Ar1、Ar2任选环合成五元环、六元环或多元环；
n表示1～5的整数。
在本发明的茚衍生物的某些实施方式中，前述的取代基相互相同或不同，各自独立地选自氢原子、氘原子、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、C1-C20链烷基、C3-C20环烷基、C2-C20烯基、C2-C20炔基、C1-C20烷氧基、C3-C20环烷烃基、C4-C20环烯烃基、苯基、联苯基、三联苯基、茚基、萘基、甘菊环基、引达省基、苊烯基、芴基、螺-二芴基、螺-苯并芴-芴基、苯并芴基、二苯并芴基、非那烯基、菲基、蒽基、荧蒽基、苯并菲基、芘基、基、苝基、并五苯基、吡咯基、噻吩基、吡喃基、噻咯基、异噻唑基、噁唑基、异噁唑基、吡啶基、吡嗪基、嘧啶基、哒嗪基、吲哚基、异吲哚基、吲唑基、嘌呤基、喹啉基、异喹啉基、苯并喹啉基、苯并异喹啉基、酞嗪基、萘啶基、喹喔啉基、苯并喹喔啉基、喹唑啉基、苯并喹唑啉基、噌啉基、菲啶基、吖啶基、啡罗啉基、吩嗪基、苯并咪唑基、苯并呋喃基、苯并噻吩基、苯并噻咯基、苯并噻唑基、苯并异噻唑基、苯并噁唑基、苯并异噁唑基、三氮唑基、四唑基、噁二唑基、三嗪基、咔唑基、氧芴基、硫芴基、硅芴基、苯并咔唑基、苯并氧芴基、苯并硫芴基、苯并硅芴基、二苯并咔唑基、二苯并氧芴基、二苯并硫芴基、二苯并硅芴基、噻二唑基、咪唑并吡啶基、咪唑并嘧啶基、噁唑并吡啶基、噻唑并吡啶基、苯并萘啶基、氮杂芴基、氮杂螺二芴基、氮杂咔唑基、氮杂氧芴基、氮杂硫芴基、氮杂硅芴基、茚并吡咯基、吲哚并吡咯基、茚并咔唑基、吲哚并咔唑基组成的组。
在本发明的茚衍生物的某些实施方式中，所述的R1、Ar1、Ar2中的所述C3-C60的杂环芳基各自独立地选自下述的II-1～II-17所示结构组成的组：
其中，Z1、Z2、Z3各自独立地选自氢原子、氘原子、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C60烷基、C2-C60烯基、C2-C60炔基、C1-C60烷氧基、C3-C60环烷烃基、C3-C60环烯烃基、C6-C60芳基、含有C1-C10烷基的C6-C60芳基、任选具有取代基的C6-C60芳氧基、任选具有取代基的C6-C60芳硫基、任选具有取代基的C3-C60杂环芳基组成的组；
x1为1～4的整数；x2为1～3的整数；x3为1～2的整数；x4为1～6的整数；x5为1～5的整数；
T1选自-B(R’)-、-N(R’)-、-P(R’)-、-O-、-S-、-Se-、-CH2-、-S(＝O)-、-S(O2)-、-C(R’R”)-、-Si(R’R”)-、-Ge(R’R”)-组成的组；
其中R’、R”各自独立地选自C1-C60烷基、C2-C60烯基、C2-C60炔基、C1-C60烷氧基、C3-C60环烷烃基、C3-C60环烯烃基、C6-C60芳基、含有C1-C10烷基的C6-C60芳基、任选具有取代基的C6-C60芳氧基、任选具有取代基的C6-C60芳硫基、任选具有取代基的C3-C60杂环芳基、以及这些基团稠合或接合而形成的环所组成的组；
表示取代基与主体结构的连接键。
在本发明的茚衍生物的某些实施方式中，前述的R1、Ar1、Ar2、Z1、Z2、或者、Z3中的所述C6-C60芳基各自独立地选自苯基、萘基、联苯基、蒽基、联蒽基、芘基、并四苯基、菲基、苯并菲基、苯并蒽基、苯并芘基、芴基、螺芴基组成的组；
前述C6-C60含氧芳基选自二苯并[b,d]呋喃-2-基、二苯并[b,d]呋喃-4-基、苯并呋喃-2-基、苯并呋喃-5-基、苯并呋喃-7-基、9,9-二甲基氧杂蒽-4-基、9,9-二甲基氧杂蒽-2-基、螺[芴-9,9’-氧杂蒽]-2’-基、螺[芴-9,9’-氧杂蒽]-2-基组成的组；
前述C6-C60含硫芳基选自二苯并[b,d]噻吩-2-基、二苯并[b,d]噻吩-4-基、4-苯亚砜基苯基、4-苯砜基苯基、苯并噻吩-2-基、苯并噻吩-5-基、苯并噻吩-7-基、9,9-二甲基硫杂蒽-4-基、9,9-二甲基硫杂蒽-2-基、螺[芴-9,9’-硫杂蒽]-2’-基、螺[芴-9,9’-硫杂蒽]-2-基组成的组；
前述C6-C60含膦芳基选自4-(二苯基氧膦基)苯基、3-(二苯基氧膦基)苯基、二苯并[b]氧膦-5-(4-苯基)-4-基组成的组；
前述C6-C60含硅芳基选自4-(三苯基硅基)苯基、4-(二苯基甲基硅基)苯基、3-(三苯基硅基)苯基、3-(二苯基甲基硅基)苯基组成的组；
前述C6-C60含硼芳基选自4-(二(2,4,6-三甲基)苯基)-硼烷苯基、二苯并[b,d]硼烷-5-苯基-4-基、三苯基硼基组成的组；
前述C6-C60含氮芳基选自由任选具有取代基的C3-C60杂环芳基、任选具有取代基的C6-C60芳基与氮原子组成的群组；
前述任选具有取代基的C3-C60杂环芳基中的杂原子选自N、O、S组成的组。
在本发明的茚衍生物的某些实施方式中，本发明的具有式I所示结构的茚衍生物选自下述的式P01～P218所示结构组成的组。
作为本发明的另一个目的，本发明还提供一种材料，该材料包含本发明的茚衍生物。
在本发明的材料的某些实施方式中，前述材料为有机电致发光材料。本发明的有机电致发光材料中包括本发明的茚衍生物中的一种或多种。本发明的有机电致发光材料可以仅由本发明的茚衍生物的一种或多种形成，也可以含有本发明的茚衍生物之外的其他材料。
通过在本发明的有机电致发光材料中含有本发明的茚衍生物，由于本发明的茚衍生物具有较大的空间位阻和载流子迁移率，从而，利用该茚衍生物制备得到的有机电致发光材料能够明显降低驱动电压、提高发光效率和亮度。
作为本发明的再一目的，本发明还提供一种有机电致发光器件，其包括第一电极、第二电极和置于所述第一电极、所述第二电极之间的空穴传输层、有机发光层、电子传输层，所述空穴传输层、有机发光层、电子传输层中的至少一层包含本发明的茚衍生物中的一种或多种。本发明的有机电致发光器件既可以是顶发射光器件，又可以是底发射光器件。另外，本发明对有机电致发光器件的结构和制备方法不做限定。采用本发明的茚衍生物制得的有机电致发光器件可降低启动电压、提高发光效率和亮度。
本发明的有机电致发光器件的某些实施方式中，有机电致发光器件的有机发光层中含有本发明的茚衍生物。具体地，例如，可以采用下述的实施方式：
在有机发光层中包含作为发光主体的选自萘、蒽、芘、苝、菲、荧蒽、苯并蒽、并五苯以及它们的衍生物中的一种以上、以及作为掺杂物的一种以上的本发明的茚衍生物。在这种情况下，对于本发明的有机电致发光器件的其他层的材料不做限定，本领域技术人员能够根据本领域的常识进行适宜选择。
作为本发明的有机电致发光器件的制造方法，除非另有规定，可以通过任何合适方法来沉积各层中的任一者，对于有机层，优选方法包括热蒸发、喷墨、有机气相沉积、通过有机蒸气喷射印刷的沉积等方法来制备。另外，也可以采用其他适宜的方法如旋涂、其它基于溶液的工艺等。基于溶液的工艺优选在氮气或惰性气氛中进行。对于有机层之外的其它层，优选通过热蒸发等工艺来形成。
另外，如无特殊说明，本发明中所用原料均可通过市售商购获得，本发明所记载的任何范围包括端值以及端值之间的任何数值以及端值或者端值之间的任意数值所构成的任意子范围。
本发明的有益效果：
本发明的式I所示的茚衍生物具有易溶解于有机溶媒的能力，利用本发明的含有茚衍生物的材料制备的有机电致发光器件可降低启动电压、提高发光效率和亮度。这一系列衍生物有较好的成膜性能，并且材料合成以及提纯的方法简单适于大规模生产等特点，是作为有机电致发光器件电子传输材料的理想选择。
附图说明
图1示出本发明实施例10中的OLED器件结构示意图。
图2示出在室温下使用稳态荧光光谱仪测定得到的茚衍生物P40的荧光光谱。
图3示出在室温下使用紫外-可见光分光光度仪检测得到的茚衍生物P40的紫外吸收光谱。
具体实施方式
为了更清楚地说明本发明，下面结合优选实施例和附图对本发明做进一步的说明。附图中相似的部件以相同的附图标记进行表示。本领域技术人员应当理解，下面所具体描述的内容是说明性的而非限制性的，不应以此限制本发明的保护范围。
在本发明的描述中，除非另有说明，“多个”的含义是两个或两个以上；术语“上”、“下”等指示的方位或位置关系为基于附图所示的方位或位置关系，仅是为了便于描述本发明和简化描述，而不是指示或暗示所指的装置或器件必须具有特定的方位、以特定的方位构造和操作，因此不能理解为对本发明的限制。
本发明中，制备方法如无特殊说明则均为常规方法。所用的原料如无特别说明均可从公开的商业途径获得，所述百分比如无特殊说明，均为质量百分比。
下述实施例对OLED材料及器件进行性能测试的测试仪器及方法如下：
OLED器件性能检测条件：
亮度和色度坐标：使用光谱扫描仪PhotoResearch PR-715测试；
电流密度和起亮电压：使用数字源表Keithley 2420测试；
功率效率：使用NEWPORT 1931-C测试。
实施例1
化合物P01的制备：
化合物P01的制备，包括如下反应步骤：
第一步：中间体Int.-1的制备
15.0g(59.7mmol)的4-(1,3,3-三甲基茚满-1-)苯胺和11.6g(49.7mmol)的4-溴联苯、6.9g(71.8mmol)的叔丁醇钠混合，再加入273.6mg(0.29mmol)的Pd2(dba)3催化剂和150mL的甲苯，在氮气保护下，再加入1.2mL的10％三叔丁基磷甲苯溶液，升温至90℃搅拌反应16小时，冷却到室温，加入80mL水，分出有机相，水相用乙酸乙酯萃取，有机相用无水硫酸钠干燥，过滤，滤液减压浓缩干，用乙醇重结晶，得18.3g灰白色固体，收率76％。
第二步：化合物P01的制备
10.0g(24.7mmol)上步制备的中间体Int-1和10.9g(27.2mmol)的3-(4-溴苯基)-9-苯基-咔唑、3.6g(37.5mmol)的叔丁醇钠混合，再加入227.0mg(0.19mmol)的Pd2(dba)3催化剂和150mL的二甲苯，在氮气保护下，再加入1.0mL的10％三叔丁基磷甲苯溶液，升温至100℃搅拌反应20小时，冷却到室温，加入80mL水，分出有机相，水相用乙酸乙酯萃取，有机相用无水硫酸钠干燥，过滤，滤液减压浓缩干，用二甲苯-石油醚重结晶，得12.8g黄色固体，收率72％。HRMS：C54H44N2，标准分子量720.3504，测试结果720.3498。
实施例2
化合物P40的制备：
化合物P40的制备，包括如下反应步骤：
第一步：中间体Int.-3的制备
合成操作参照实施例1的第一步，将实施例1第一步的4-溴联苯替换为4-溴二苯并呋喃，得到中间体Int.-3，黄色固体，收率78％。
第二步：化合物P40的制备
10.0g(23.9mmol)上步制备的中间体Int-3和4.4g(10.0mmol)的1,6-二溴-3,8-二异丙基芘、2.9g(30.0mmol)的叔丁醇钠混合，再加入91.5mg(0.1mmol)的Pd2(dba)3催化剂和100mL的甲苯，在氮气保护下，再加入0.5mL的10％三叔丁基磷甲苯溶液，升温至100℃搅拌反应20小时，冷却到室温，加入50mL水，分出有机相，水相用二氯甲烷萃取，有机相用无水硫酸钠干燥，过滤，滤液减压浓缩干，用甲苯-二氯甲烷重结晶，得7.5g黄色固体，收率68％。HRMS：C82H72N2O2，标准分子量1116.5594，测试结果1116.5526。将P40溶于二氯甲烷中，配制成1×10-5mol/L的溶液，在室温下使用稳态荧光光谱仪测定其荧光光谱，见附图2，在室温下使用紫外-可见光分光光度仪检测紫外吸收光谱，见附图3。
实施例3
化合物P92的制备：
化合物P92的制备，包括如下反应步骤：
第一步：中间体Int.-5的制备
合成操作参照实施例1的第一步，将实施例1第一步的4-溴联苯替换为对溴苯甲醚，得到中间体Int.-5，白色的固体，收率66％。
第二步：化合物P92的制备
合成操作参照实施例2的第二步，将实施例2第二步的Int.-3替换为Int.-5，将实施例2第二步的1,6-二溴-3,8-二异丙基芘替换为Int.-6，得到化合物P92，白色固体，收率72％。HRMS：C87H70N2O4，标准分子量1206.5336，测试结果1206.5270。
实施例4
化合物P105的制备：
化合物P105的制备，包括如下反应步骤：
第一步：中间体Int.-7的制备
合成操作参照实施例1的第一步，将实施例1第一步的4-溴联苯替换为3-溴-9-苯基咔唑，得到中间体Int.-7，黄色的固体，收率74％。
第二步：化合物P105的制备
合成操作参照实施例2的第二步，将实施例2第二步的Int.-3替换为Int.-7，将实施例2第二步的1,6-二溴-3,8-二异丙基芘替换为9,10-二溴蒽，得到化合物P105，黄色固体，收率45％。HRMS：C86H70N4，标准分子量1158.5600，测试结果1158.5671。
实施例5
参照实施例1、实施例2、实施例3和实施例4的合成方法，制备化合物P02～P39、P41～P91、P93～P104、P106～P144、P157～P162、P183～P190、P194～P218，即方法步骤同实施例1、实施例2、实施例3和实施例4，不同之处仅在于根据所需产物不同，根据实际需要采用不同的化合物替换实施例1第一步的4-溴联苯，并根据摩尔量更改该化合物的质量用量，制备目标化合物。
实施例6
化合物P154的制备：
化合物P154的制备，包括如下反应步骤：
第一步：中间体Int.-8的制备
合成操作参照实施例1的第一步，将实施例1第一步的4-溴联苯替换为邻溴硝基苯，得到中间体Int.-8，黄色的固体，收率82％。
第二步：中间体Int-9的制备
10.0g(26.8mmol)上步制备的中间体Int-8溶解在200mL的甲醇中，加入0.5g的10％钯/碳，室温下通入氢气至0.2MPa，搅拌反应10小时，过滤，滤液减压浓缩干，无需纯化，得9.1g黄色固体，收率99％。
第三步：中间体Int-10的制备
9.0g(26.2mmol)上步制备的中间体Int-9溶解在120mL的乙醇中，加入4.9g(26.2mmol)的对溴苯甲醛，加入5.0g(64.9mmol)的醋酸铵和0.4g(4.3mmol)的氢氧化钴，加热升温回流搅拌反应4小时，减压浓缩干，用硅胶柱分离纯化，得12.7g黄色固体，收率95％。
第四步：中间体Int-11的制备
12.0g(23.6mmol)上步制备的中间体Int-10溶解在120mL的干燥THF中，加入3.0g(28.3mmol)的硼酸三甲酯，在氮气保护下，用液氮降温至-78℃，滴加入11.3mL的2.5M正丁基锂正己烷溶液，保温搅拌反应30分钟，自然升到室温，搅拌反应1小时，滴加入50mL的2N稀盐酸搅拌反应30分钟，用乙酸乙酯萃取，收集有机相，干燥，过滤，滤液减压浓缩干，加入石油醚分散，过滤，得9.4g白色固体，收率84％。
第五步：中间体Int-12的制备
9.0g(19.0mmol)上步制备的中间体Int-11、1.7g(9.2mmol)的三聚氯氰、2.0g(19.0mmol)的无水碳酸钠，再加入106mg(0.09mmol)的Pd(PPh3)4催化剂，加入60mL的甲苯、40mL的乙醇和20mL的水，在氮气保护下，升温回流搅拌反应12小时，冷却到室温，用乙酸乙酯萃取，收集有机相，干燥，过滤，滤液减压浓缩干，用乙醇重结晶，得7.7g白色固体，收率86％。
第六步：化合物P154的制备
3.0g(9.3mmol)的二(4-联苯基)胺溶解在80mL的N,N-二甲基甲酰胺中，在氮气保护下，用冰水浴降温至0℃，分批加入0.4g(10.0mmol，60％)的氢化钠，搅拌反应1小时，加入7.5g(7.7mmol)上步制备的中间体Int-12、于室温搅拌反应12小时，将反应液倒入200mL的冰水中，过滤，滤饼用水洗，用乙醇重结晶，得8.7g白色固体，收率90％。HRMS：C89H72N8，标准分子量1252.5880，测试结果1252.5814。
实施例7
参照实施例6的合成方法，制备化合物P145～P153、P155、P156、P163～P167，即方法步骤同实施例6，不同之处仅在于根据所需产物不同，根据实际需要采用不同的化合物替换实施例6第五步的三聚氯氰，并根据摩尔量更改该化合物的质量用量，制备目标化合物。
实施例8
化合物P169的制备：
化合物P169的制备，包括如下反应步骤：
第一步：中间体Int.-13的制备
5.0g(15.8mmol)的1-(4-溴苯基)-1,3,3-三甲基茚满和2.4g(14.4mmol)的咔唑、2.1g(21.8mmol)的叔丁醇钠混合，再加入32.5mg(0.14mmol)的Pd(OAc)2催化剂和50mL的二甲苯，在氮气保护下，再加入0.2mL的10％三叔丁基磷甲苯溶液，升温回流搅拌反应20小时，冷却到室温，加入50mL水，分出有机相，水相用甲苯萃取，有机相用无水硫酸钠干燥，过滤，滤液减压浓缩干，用乙醇重结晶，得4.2g黄色固体，收率74％。
第二步：中间体Int.-14的制备
5.0g(12.4mmol)上步制备的中间体Int-13溶解于50mL的甲苯和50mL的乙酸乙酯中、加入2.2g(12.4mmol)的NBS固体，于室温搅拌反应48小时，加入50mL的水，分出有机相，水相用乙酸乙酯萃取，有机相用无水硫酸钠干燥，过滤，滤液减压浓缩干，用石油醚重结晶，得5.1g白色固体，收率86％。
第三步：化合物P169的制备
5.0g(10.4mmol)上步制备的中间体Int-14、4.5g(12.3mmol)的9-(4-联苯基)咔唑-3-硼酸、2.2g(20.7mmol)的无水碳酸钠，再加入60.0mg(0.05mmol)的Pd(PPh3)4催化剂，加入60mL的甲苯、40mL的乙醇和20mL的水，在氮气保护下，升温回流搅拌反应12小时，冷却到室温，用乙酸乙酯萃取，收集有机相，干燥，过滤，滤液减压浓缩干，用乙醇重结晶，得6.4g白色固体，收率85％。HRMS：C54H42N2，标准分子量718.3348，测试结果719.3444。
实施例9
参照实施例8的合成方法，制备化合物P168、P170～P182、P191～P193，即方法步骤同实施例8，不同之处仅在于根据所需产物不同，根据实际需要采用不同的化合物替换实施例8第三步的9-(4-联苯基)咔唑-3-硼酸，并根据摩尔量更改该化合物的质量用量，制备目标化合物。
实施例10
一种OLED器件，如图1所示，包括基板1、设于基板1上的阳极层2、设于阳极层2上的空穴注入层3、设于空穴注入层3上的空穴传输层4、设于空穴传输层4上的电子阻挡层5、设于电子阻挡层5上的有机发光层6、设于有机发光层6上的空穴阻挡层7、设于空穴阻挡层7上的电子传输层8、设于电子传输层8上的阴极层9，其制备包括如下步骤：
1)将涂布了ITO导电层的玻璃基片在清洗剂中超声处理30分钟，在去离子水中冲洗，在丙酮/乙醇混合溶剂中超声30分钟，在洁净的环境下烘烤至完全干燥，用紫外光清洗机照射10分钟，并用低能阳离子束轰击表面。
2)把上述处理好的ITO玻璃基片置于真空腔内，抽真空至1×10-5～9×10-3Pa，在上述阳极层膜上蒸镀化合物2-TNATA作为空穴注入层，蒸镀速率为0.1nm/s，蒸镀膜厚为40nm；
3)在上述空穴注入层上继续蒸镀NPB为空穴传输层，蒸镀速率为0.1nm/s，蒸镀膜厚为10nm；
4)在空穴传输层上继续蒸镀MADN为主体材料和本发明的化合物式I为掺杂材料，MADN:式I的质量比为98:2，作为器件的有机发光层，蒸镀速率为0.1nm/s，蒸镀所得有机发光层的膜厚为40nm；
5)在有机发光层上继续蒸镀一层LiQ为电子传输层，蒸镀速率为0.1nm/s，蒸镀膜厚为20nm；
6)在电子传输层之上依次蒸镀镁/银合金层作为器件的阴极层，其中镁/银合金层的蒸镀速率为2.0～3.0nm/s，蒸镀膜厚为100nm，镁和银的质量比为1：9，得到本发明提供的OLED器件。
按照与上相同的步骤，将步骤4)中的化合物式I选为P40，得到本发明提供的OLED-1；
按照与上相同的步骤，将步骤4)中的化合物式I选为P92，得到本发明提供的OLED-2；
按照与上相同的步骤，将步骤4)中的化合物式I选为BD01，得到本发明的对比器件OLED-3；
按照与上相同的步骤，将步骤3)中的NPB替换为P07，将步骤4)中的化合物式I选为BD01，得到本发明提供的OLED-4；
按照与上相同的步骤，将步骤3)中的NPB替换为P09，将步骤4)中的化合物式I选为BD01，得到本发明提供的OLED-5；
其中，BD01为：
所得器件OLED-1至OLED-5的性能检测结果如表1所示。
表1 OLED-1至OLED-5的性能检测结果
由上可知，使用本发明的有机材料作为发光层的掺杂材料制备成的器件起亮电压低，在电流密度相同的条件下，亮度和效率明显较对比材料BD01的高，色度坐标更偏向于深蓝区，而且器件的寿命要延长2倍以上。
使用本发明的有机材料作为空穴传输层材料制备成的器件，亮度和效率明显较对比材料NPB的高，而且器件的寿命要好很多，说明本发明的材料稳定性要好，电力消耗更低。
显然，本发明的上述实施例仅仅是为清楚地说明本发明所作的举例，而并非是对本发明的实施方式的限定，对于所属领域的普通技术人员来说，在上述说明的基础上还可以做出其它不同形式的变化或变动，这里无法对所有的实施方式予以穷举，凡是属于本发明的技术方案所引伸出的显而易见的变化或变动仍处于本发明的保护范围之列。

Claims (9)

1.一种茚衍生物，其特征在于，所述茚衍生物的结构式如下述的式I所示：
其中，R1表示氢原子、氘原子、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、C1-C20链烷基、C3-C20环烷基、C2-C20烯基、C2-C20炔基、C1-C20烷氧基、C3-C20环烷烃基、C4-C20环烯烃基、C1-C20杂烷基、任选具有取代基的C6-C60芳基、任选具有取代基的C6-C60芳香乙烯基、任选具有取代基的C6-C60稠环芳香基、任选具有取代基的C6-C60芳胺基、任选具有取代基的C6-C60含氮原子的稠环芳基、任选具有取代基的C6-C60含硫或氧原子的稠环芳基、任选具有取代基的C6-C60含磷、硅或硼原子的稠环芳基、或任选具有取代基的C3-C60杂环芳基；
Ar1、Ar2各自独立地选自任选具有取代基的C6-C60芳基、任选具有取代基的C6-C60含氧芳基、任选具有取代基的C6-C60含硫芳基、任选具有取代基的C6-C60含磷芳基、任选具有取代基的C6-C60含氮芳基、任选具有取代基的C6-C60含硅芳基、任选具有取代基的C6-C60含硼芳基、任选具有取代基的C6-C60稠环芳香基、任选具有取代基的C6-C60芳胺基、任选具有取代基的C3-C60杂环芳基组成的组，Ar1、Ar2任选环合成五元环、六元环或多元环；
n表示1～5的整数。
2.根据权利要求1所述的茚衍生物，其特征在于，所述取代基相互相同或不同，各自独立地选自氢原子、氘原子、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、C1-C20链烷基、C3-C20环烷基、C2-C20烯基、C2-C20炔基、C1-C20烷氧基、C3-C20环烷烃基、C4-C20环烯烃基、苯基、联苯基、三联苯基、茚基、萘基、甘菊环基、引达省基、苊烯基、芴基、螺-二芴基、螺-苯并芴-芴基、苯并芴基、二苯并芴基、非那烯基、菲基、蒽基、荧蒽基、苯并菲基、芘基、基、苝基、并五苯基、吡咯基、噻吩基、吡喃基、噻咯基、异噻唑基、噁唑基、异噁唑基、吡啶基、吡嗪基、嘧啶基、哒嗪基、吲哚基、异吲哚基、吲唑基、嘌呤基、喹啉基、异喹啉基、苯并喹啉基、苯并异喹啉基、酞嗪基、萘啶基、喹喔啉基、苯并喹喔啉基、喹唑啉基、苯并喹唑啉基、噌啉基、菲啶基、吖啶基、啡罗啉基、吩嗪基、苯并咪唑基、苯并呋喃基、苯并噻吩基、苯并噻咯基、苯并噻唑基、苯并异噻唑基、苯并噁唑基、苯并异噁唑基、三氮唑基、四唑基、噁二唑基、三嗪基、咔唑基、氧芴基、硫芴基、硅芴基、苯并咔唑基、苯并氧芴基、苯并硫芴基、苯并硅芴基、二苯并咔唑基、二苯并氧芴基、二苯并硫芴基、二苯并硅芴基、噻二唑基、咪唑并吡啶基、咪唑并嘧啶基、噁唑并吡啶基、噻唑并吡啶基、苯并萘啶基、氮杂芴基、氮杂螺二芴基、氮杂咔唑基、氮杂氧芴基、氮杂硫芴基、氮杂硅芴基、茚并吡咯基、吲哚并吡咯基、茚并咔唑基、吲哚并咔唑基组成的组。
3.根据权利要求1或2所述的茚衍生物，其特征在于，所述的R1、Ar1、Ar2中的所述C3-C60的杂环芳基各自独立地选自下述的II-1～II-17所示结构组成的组：
其中，Z1、Z2、Z3各自独立地选自氢原子、氘原子、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C60烷基、C2-C60烯基、C2-C60炔基、C1-C60烷氧基、C3-C60环烷烃基、C3-C60环烯烃基、C6-C60芳基、含有C1-C10烷基的C6-C60芳基、任选具有取代基的C6-C60芳氧基、任选具有取代基的C6-C60芳硫基、任选具有取代基的C3-C60杂环芳基组成的组；
x1为1～4的整数；x2为1～3的整数；x3为1～2的整数；x4为1～6的整数；x5为1～5的整数；
T1选自-B(R’)-、-N(R’)-、-P(R’)-、-O-、-S-、-Se-、-CH2-、-S(＝O)-、-S(O2)-、-C(R’R”)-、-Si(R’R”)-、-Ge(R’R”)-组成的组；
其中R’、R”各自独立地选自C1-C60烷基、C2-C60烯基、C2-C60炔基、C1-C60烷氧基、C3-C60环烷烃基、C3-C60环烯烃基、C6-C60芳基、含有C1-C10烷基的C6-C60芳基、任选具有取代基的C6-C60芳氧基、任选具有取代基的C6-C60芳硫基、任选具有取代基的C3-C60杂环芳基、以及这些基团稠合或接合而形成的环所组成的组；
表示取代基与主体结构的连接键。
4.根据权利要求1～3的任一项所述的茚衍生物，其特征在于，所述的R1、Ar1、Ar2、Z1、Z2、或者、Z3中的所述C6-C60芳基各自独立地选自苯基、萘基、联苯基、蒽基、联蒽基、芘基、并四苯基、菲基、苯并菲基、苯并蒽基、苯并芘基、芴基、螺芴基组成的组；
所述C6-C60含氧芳基选自二苯并[b,d]呋喃-2-基、二苯并[b,d]呋喃-4-基、苯并呋喃-2-基、苯并呋喃-5-基、苯并呋喃-7-基、9,9-二甲基氧杂蒽-4-基、9,9-二甲基氧杂蒽-2-基、螺[芴-9,9’-氧杂蒽]-2’-基、螺[芴-9,9’-氧杂蒽]-2-基组成的组；
所述C6-C60含硫芳基选自二苯并[b,d]噻吩-2-基、二苯并[b,d]噻吩-4-基、4-苯亚砜基苯基、4-苯砜基苯基、苯并噻吩-2-基、苯并噻吩-5-基、苯并噻吩-7-基、9,9-二甲基硫杂蒽-4-基、9,9-二甲基硫杂蒽-2-基、螺[芴-9,9’-硫杂蒽]-2’-基、螺[芴-9,9’-硫杂蒽]-2-基组成的组；
所述C6-C60含膦芳基选自4-(二苯基氧膦基)苯基、3-(二苯基氧膦基)苯基、二苯并[b]氧膦-5-(4-苯基)-4-基组成的组；
所述C6-C60含硅芳基选自4-(三苯基硅基)苯基、4-(二苯基甲基硅基)苯基、3-(三苯基硅基)苯基、3-(二苯基甲基硅基)苯基组成的组；
所述C6-C60含硼芳基选自4-(二(2,4,6-三甲基)苯基)-硼烷苯基、二苯并[b,d]硼烷-5-苯基-4-基、三苯基硼基组成的组；
所述C6-C60含氮芳基选自由任选具有取代基的C3-C60杂环芳基、任选具有取代基的C6-C60芳基与氮原子组成的群组；
所述任选具有取代基的C3-C60杂环芳基中的杂原子选自N、O、S组成的组。
5.根据权利要求1～4的任一项所述的茚衍生物，其特征在于，所述茚衍生物选自下述的式P01～P218所示的结构式组成的组：
6.一种有机电致发光器件，其特征在于，所述有机电致发光装置包括第一电极、第二电极和置于所述第一电极、所述第二电极之间的空穴传输层、有机发光层、电子传输层，所述空穴传输层、有机发光层、电子传输层中的至少一层包含权利要求1～5的任一项所述的茚衍生物中的一种或多种。
7.根据权利要求6所述的有机电致发光器件，其特征在于，所述有机发光层中含有权利要求1～5的任一项所述的茚衍生物。
8.如权利要求7所述的有机电致发光器件，其特征在于，所述有机发光层包含作为发光主体的选自萘、蒽、芘、苝、菲、荧蒽、苯并蒽、并五苯以及它们的衍生物中的一种以上、以及作为掺杂物的一种以上的权利要求1～5的任一项所述的茚衍生物。
9.权利要求1～5任一项所述的茚衍生物在制备有机电致发光器件中的应用。
CN201910260776.XA 2019-04-02 2019-04-02 茚衍生物、含有茚衍生物的有机电致发光器件 Active CN110003090B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201910260776.XA CN110003090B (zh) 2019-04-02 2019-04-02 茚衍生物、含有茚衍生物的有机电致发光器件

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201910260776.XA CN110003090B (zh) 2019-04-02 2019-04-02 茚衍生物、含有茚衍生物的有机电致发光器件

Publications (2)

Publication Number Publication Date
CN110003090A true CN110003090A (zh) 2019-07-12
CN110003090B CN110003090B (zh) 2021-01-08

Family

ID=67169433

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201910260776.XA Active CN110003090B (zh) 2019-04-02 2019-04-02 茚衍生物、含有茚衍生物的有机电致发光器件

Country Status (1)

Country Link
CN (1) CN110003090B (zh)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113451522A (zh) * 2021-06-28 2021-09-28 冠能光电材料(深圳)有限责任公司 一种多功能有机芳胺半导体材料及其发光器件应用
CN114394949A (zh) * 2022-01-25 2022-04-26 长春海谱润斯科技股份有限公司 一种联苯胺衍生物及其有机电致发光器件
CN114605314A (zh) * 2022-03-30 2022-06-10 上海八亿时空先进材料有限公司 一种茚衍生物及其应用
CN114907231A (zh) * 2022-06-22 2022-08-16 杭州师范大学 一种茚类手性螺环荧光化合物及其制备方法与应用
US11437581B2 (en) * 2019-05-24 2022-09-06 Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. Blue fluorescent material and display panel

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08259936A (ja) * 1995-03-24 1996-10-08 Toyo Ink Mfg Co Ltd 正孔輸送材料およびその用途
CN108218721A (zh) * 2016-12-15 2018-06-29 阜阳欣奕华材料科技有限公司 一种苯基茚类化合物、有机电致发光器件及显示装置
CN108218788A (zh) * 2016-12-15 2018-06-29 阜阳欣奕华材料科技有限公司 一种苯基茚类化合物、有机电致发光器件及显示装置
CN108456161A (zh) * 2018-02-08 2018-08-28 王美妮 苯基茚类化合物、有机电致发光器件及显示装置
WO2018206769A1 (en) * 2017-05-12 2018-11-15 Dottikon Es Holding Ag Indane derivatives and their use in organic electronics

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08259936A (ja) * 1995-03-24 1996-10-08 Toyo Ink Mfg Co Ltd 正孔輸送材料およびその用途
CN108218721A (zh) * 2016-12-15 2018-06-29 阜阳欣奕华材料科技有限公司 一种苯基茚类化合物、有机电致发光器件及显示装置
CN108218788A (zh) * 2016-12-15 2018-06-29 阜阳欣奕华材料科技有限公司 一种苯基茚类化合物、有机电致发光器件及显示装置
WO2018206769A1 (en) * 2017-05-12 2018-11-15 Dottikon Es Holding Ag Indane derivatives and their use in organic electronics
CN108456161A (zh) * 2018-02-08 2018-08-28 王美妮 苯基茚类化合物、有机电致发光器件及显示装置

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11437581B2 (en) * 2019-05-24 2022-09-06 Wuhan China Star Optoelectronics Semiconductor Display Technology Co., Ltd. Blue fluorescent material and display panel
CN113451522A (zh) * 2021-06-28 2021-09-28 冠能光电材料(深圳)有限责任公司 一种多功能有机芳胺半导体材料及其发光器件应用
CN114394949A (zh) * 2022-01-25 2022-04-26 长春海谱润斯科技股份有限公司 一种联苯胺衍生物及其有机电致发光器件
CN114394949B (zh) * 2022-01-25 2023-11-10 长春海谱润斯科技股份有限公司 一种联苯胺衍生物及其有机电致发光器件
CN114605314A (zh) * 2022-03-30 2022-06-10 上海八亿时空先进材料有限公司 一种茚衍生物及其应用
CN114605314B (zh) * 2022-03-30 2024-04-02 上海八亿时空先进材料有限公司 一种茚衍生物及其应用
CN114907231A (zh) * 2022-06-22 2022-08-16 杭州师范大学 一种茚类手性螺环荧光化合物及其制备方法与应用
CN114907231B (zh) * 2022-06-22 2024-02-23 杭州师范大学 一种茚类手性螺环荧光化合物及其制备方法与应用

Also Published As

Publication number Publication date
CN110003090B (zh) 2021-01-08

Similar Documents

Publication Publication Date Title
CN110003090A (zh) 茚衍生物、含有茚衍生物的有机电致发光器件
TWI461507B (zh) 新穎有機電場發光化合物及使用該化合物之有機電場發光裝置
CN110229071A (zh) 芴衍生物有机电致发光器件
CN108336246B (zh) 一种有机发光器件
CN107556310B (zh) 咪唑衍生物、包含该咪唑衍生物的材料和有机电致发光器件
CN109467543A (zh) 一种三芳胺衍生物及其有机电致发光器件
CN112266371B (zh) 含氮化合物以及电子元件和电子装置
WO2020250700A1 (ja) 多環芳香族化合物
CN107001370A (zh) 杂环化合物和使用其的有机发光器件
CN107257787A (zh) 杂环化合物和包含其的有机发光元件
CN115073461A (zh) 一种咔唑衍生物及其在有机发光元件中的应用
CN114685484B (zh) 一种有机电致发光化合物及包含其的有机电致发光器件
CN112209937B (zh) 一种有机含氮杂环化合物及其应用
CN111377905A (zh) 有机电致发光材料及器件
CN109535137A (zh) 一种含有咔唑基团的三芳胺类化合物及其有机发光器件
CN114853766A (zh) 一种咔唑稠环取代的三嗪类化合物及其应用
CN110041209A (zh) 一种芳胺类化合物、包含该芳胺类化合物的材料和有机电致发光器件
CN109485576A (zh) 有机电致发光器件用材料及包含其的有机电致发光器件
CN115215871B (zh) 有机化合物以及使用其的有机电致发光器件和电子装置
CN115322177A (zh) 一种芴衍生物及其应用
CN108822156A (zh) 一种含金属的有机络合物及其有机发光器件
CN110894203B (zh) 有机发光化合物及其应用和有机电致发光器件
CN114685288A (zh) 多环芳胺类有机化合物及其用途
CN108250084A (zh) 一种芴类衍生物及其有机发光器件
EP4186892A1 (en) Novel compound, coating composition comprising same, organic light-emitting device using same, and manufacturing method therefor

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
TA01 Transfer of patent application right
TA01 Transfer of patent application right

Effective date of registration: 20191226

Address after: 050000 No. 362 Pearl River Avenue, Shijiazhuang City, Hebei Province

Applicant after: Shijiazhuang Chengzhi Yonghua Display Materials Co., Ltd.

Address before: Room 601-1, 6th floor, Tsinghua Tongfang Building, Tsinghua Garden, Haidian District, Beijing

Applicant before: Beijing Chengzhi Yonghua Display Technology Co., Ltd.

GR01 Patent grant
GR01 Patent grant