CN114014742B - 一种三芳基苯衍生物、发光材料、发光元件及消费型产品 - Google Patents

一种三芳基苯衍生物、发光材料、发光元件及消费型产品 Download PDF

Info

Publication number
CN114014742B
CN114014742B CN202111282565.XA CN202111282565A CN114014742B CN 114014742 B CN114014742 B CN 114014742B CN 202111282565 A CN202111282565 A CN 202111282565A CN 114014742 B CN114014742 B CN 114014742B
Authority
CN
China
Prior art keywords
group
organic electroluminescent
triarylbenzene
derivative
layer
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN202111282565.XA
Other languages
English (en)
Other versions
CN114014742A (zh
Inventor
戴雄
姜坤
曹建华
唐伟
王志杰
谢佩
李程辉
徐先锋
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shanghai 800 Million Spacetime Advanced Material Co ltd
Original Assignee
Shanghai 800 Million Spacetime Advanced Material Co ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shanghai 800 Million Spacetime Advanced Material Co ltd filed Critical Shanghai 800 Million Spacetime Advanced Material Co ltd
Priority to CN202111282565.XA priority Critical patent/CN114014742B/zh
Publication of CN114014742A publication Critical patent/CN114014742A/zh
Application granted granted Critical
Publication of CN114014742B publication Critical patent/CN114014742B/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
    • 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
    • C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
    • C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
    • C07C13/567—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered with a fluorene or hydrogenated fluorene ring system
    • 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
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C07C15/27—Polycyclic condensed hydrocarbons containing three rings
    • C07C15/28—Anthracenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
    • 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
    • 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
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • 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
    • C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/57—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/10—Aza-phenanthrenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/18—Ring systems of four or more rings
    • 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
    • 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
    • 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
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
    • C07D265/38—[b, e]-condensed with two six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings
    • C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no 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 the ring atoms
    • 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
    • C07D471/12—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 three hetero rings
    • C07D471/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • 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
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
    • 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 Table
    • 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
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/85—Arrangements for extracting light from the 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—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
    • H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen 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
    • H10K85/654—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
    • 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

本发明涉及一种三芳基苯衍生物、发光材料、发光元件及消费型产品，所述的三芳基苯衍生物的结构式如式(I)所示，所述的衍生物适用于电子元件中，特别是适用于有机电致发光装置中，并且涉及含有所述化合物的有机电致发光元件用材料、有机电致发光装置和电子设备。本发明所述的三芳基苯衍生物用作荧光或磷光发光体的基质材料时，具有非常高的效率和长寿命，所述的衍生物用于有机电致发光元件中时，具有较高的效率，并且在使用和低工作电压的情况下导致陡峭的电流‑电压曲线，本发明所述的衍生物具有高的热稳定性，并且能够在不分解和没有残余物的情况下进行升华，且具有高的氧化稳定性。

Description

一种三芳基苯衍生物、发光材料、发光元件及消费型产品
技术领域
本发明属于有机电致发光材料技术领域，具体涉及一种三芳基苯衍生物、发光材料、发光元件及消费型产品。
背景技术
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(Pope M,Kal lmann H,Magnante P.Electroluminescence in organic crystals[J].Chem.Phys.,1963,38(8):2042-2043.)，开启了有机电致发光(简称OLED)及相关的研究。经过二十几年的发展，有机发光(简称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。
最近几年有机电致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。特别是用于制作元件的各种有机材料，其载流子注入和传输性能、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。尤其是发光元件在发光效率和使用寿命还达不到实用化要求，这大大限制了OLED技术的发展。而利用三线态发光的金属配合物磷光材料具有高的发光效率，其绿光和红光材料已经达到使用要求，但是金属配合物具有特殊的电子结构特征，导致其蓝光材料无法达到使用要求。
在目前的技术发展下，无论是对于荧光材料还是对于磷光材料，特别是在用于有机电致发光器件中的工作电压、效率和寿命方面和在升华期间的热稳定性方面，都还需要改进。
鉴于以上原因，特提出本发明。
发明内容
为了解决现有技术存在的以上问题，本发明提供了一种三芳基苯衍生物、发光材料、发光元件及消费型产品，本发明所述的三芳基苯衍生物适用于荧光或磷光OLED中，具有高的热稳定性，且能够在没有分解和没有残余物的情况下进行升华。
本发明的第一目的，提供了一种三芳基苯衍生物，所述的三芳基苯衍生物的结构式如式(I)所示：
其中，R各自独立地选自氢原子、氘原子、卤素原子、腈基、具有C1～C40的直链烷基、具有C1～C40的直链杂烷基、具有C3～C40的支链或环状的烷基、具有C3～C40的支链或环状的杂烷基、具有C2～C40的烯基或炔基、具有5至60个碳原子的芳基或具有2至60个碳原子的杂芳基或NR1R2组成的群组，并且R不全部为氢或氘；
R1、R2各自相同或者不同，选自由取代或未取代的C5～C60的芳基、取代或未取代的C5～C60的芳胺基、取代或未取代的C5～C60的芳硼基、取代或未取代的C5～C60的芳磷基、取代或未取代的C2～C60的杂芳基组成的群组，R1和R2可以任选地接合或稠合形成另外的一个或多个取代或未取代的环，在所形成的环中含有或不含有一个或多个杂原子N、P、B、O、S、P＝O、或含有或不含有一个或多个CR3R4、SiR3R4；
Ar选自取代或未取代的C5～C60的亚芳基、取代或未取代的C5～C60的亚芳胺基、取代或未取代的C5～C60的亚芳硼基、取代或未取代的C5～C60的亚芳磷基、取代或未取代的C2～C60的亚杂芳基组成的群组；
n表示0～5的整数，优选的，n表示1～3的整数；
R3、R4在每次出现时相同或不同地选自氢原子、氘原子、卤素原子、腈基、具有C1～C40的直链烷基、具有C1～C40的直链杂烷基、具有C3～C40的支链或环状的烷基、具有C3～C40的支链或环状的杂烷基、具有C2～C40的烯基或炔基、具有5至60个碳原子的芳基或具有2至60个碳原子的杂芳基组成的组。
本发明人经过大量的试验发现惊讶地发现，所述的衍生物特别是在寿命、效率和工作电压方面在有机电致发光元件中引起了显著的改进。特别是将本发明的化合物用作空穴传输材料或用作基质材料时，这种情况适用于磷光和荧光的电致发光元件。所述材料通常具有高的热稳定性，并且因此能够在没有分解和没有残余物的情况下进行升华。因此，本发明涉及这些材料，并且涉及包含这种类型的化合物的电子元件。特别地，使用芳族单胺获得了非常好的结果，这是令人惊讶的结果，因为含有至少两个氮原子的空穴传输材料通常被用于有机电致发光元件中。
进一步的，所述式(I)选自由以下式(II)～式(XII)组成的群组：
其中，T选自O、S、CR3R4、NR5或SiR3R4；
其中，R3、R4、R5在每次出现时相同或不同地选自氢原子、氘原子、氟原子、腈基、具有C1～C40的直链烷基、具有C3～C40的支链或环状的烷基、具有5至60个碳原子的芳基或具有2至60个碳原子的杂芳基组成的组；
取代基R为1取代至饱和取代。
进一步的，所述基团R1和R2在每次出现时相同或不同地选自由式(2)～(33)的基团组成的群组：
其中，R3、R4、R5在每次出现时相同或不同地选自氢原子、氘原子、氟原子、腈基、具有C1～C40的直链烷基、具有C3～C40的支链或环状的烷基、具有5至60个碳原子的芳基或具有2至60个碳原子的杂芳基组成的组；
其中，虚线键指示与N连接的位置。
进一步的，所述基团Ar选自由式(34)至(58)所示的结构组成的群组：
其中，一个虚线键指示与所述三芳基苯主体中苯的键合，而另一个虚线指示与N或R的键合；
R3、R4、R5在每次出现时相同或不同地选自氢原子、氘原子、氟原子、腈基、具有C1～C40的直链烷基、具有C3～C40的支链或环状的烷基、具有5至60个碳原子的芳基或具有2至60个碳原子的杂芳基组成的组。
进一步的，所述基团(2)至(58)中的R特别优选代表为氢。
进一步的，所述R3、R4特别优选代表为甲基、苯基、芴基。
进一步的，所述基团R5特别优选代表为甲基、乙基、苯基、萘基、菲基、联苯基、三亚苯基。
本发明意义上的芳基含有6～60个碳原子，在本发明意义上的杂芳基含有2～60个碳原子和至少一个杂原子，其条件是碳原子和杂原子的总和至少是5；所述杂原子优选自N、O或S。此处的芳基或杂芳基被认为是指简单的芳族环，即苯、萘等，或简单的杂芳族环，如吡啶、嘧啶、噻吩等。或稠合的芳基或杂芳基，如蒽、菲、苯并菲、喹啉、异喹啉、蒽啶等。或者是由简单的芳基，例如苯、萘、菲、吡啶等或这些基团的组合与一个或多个非芳族单元例如C、N、O或S原子构建，因此，例如，和其中两个或更多个芳基被例如短的烷基连接的体系一样，诸如芴、9,9’-螺二芴、9,9-二芳基芴、咔唑、二芳基醚、二苯并呋喃、二苯并噻吩等。
对于本发明意义上的烷基含有1～40个碳原子，并且其中单独的氢原子或-CH2-基团还可被上述基团R取代的脂族烃基，优选被认为是指如下基团：甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、新戊基、环戊基、正己基、新己基、环己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、环己烯基、庚烯基、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛炔基、甲氧基、三氟甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、仲戊氧基、2-甲基丁氧基、正己氧基、环己氧基、正庚氧基、环庚氧基、正辛氧基、环辛氧基、2-乙基己氧基、五氟乙氧基和2,2,2-三氟乙氧基。杂烷基优选具有1～40个碳原子的烷基，是指其中单独的氢原子或-CH2-基团可被氧、硫、卤素原子取代的基团，被认为是指烷氧基、烷硫基、氟代的烷氧基、氟代的烷硫基，特别是指甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、三氟甲硫基、三氟甲氧基、五氟乙氧基、五氟乙硫基、2,2,2-三氟乙氧基、2,2,2-三氟乙硫基、乙烯氧基、乙烯硫基、丙烯氧基、丙烯硫基、丁烯硫基、丁烯氧基、戊烯氧基、戊烯硫基、环戊烯氧基、环戊烯硫基、己烯氧基、己烯硫基、环己烯氧基、环己烯硫基、乙炔氧基、乙炔硫基、丙炔氧基、丙炔硫基、丁炔氧基、丁炔硫基、戊炔氧基、戊炔硫基、己炔氧基、己炔硫基。
一般来说，根据本发明的环烷基、环烯基可为环丙基、环丁基、环戊基、环己基、环丁烯基、环戊烯基、环己烯基、环庚基、环庚烯基，其中一个或多个-CH2-基团可被上述基团代替；此外，一个或多个氢原子还可被氘原子、卤素原子或腈基代替。
根据本发明的烯基或炔基具有2～40个碳原子，并且其中单独的氢原子可被上述基团R取代的烯基或炔基，优选为乙烯基、丙烯基、丁烯基、异丁烯基、苯乙烯基、二苯乙烯基、乙炔基、丙炔基、丁炔基、苯乙炔基；此外，一个或多个氢原子还可被氘原子、卤素原子或腈基代替。
进一步的，根据本发明的芳基或杂芳基，特别是指衍生自如下物质的基团：苯、萘、蒽、苯并蒽、菲、芘、苝、荧蒽、并四苯、并五苯、苯并芘、联苯、偶苯、三联苯、三聚苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或反式茚并芴、顺式或反式茚并咔唑、顺式或反式吲哚并咔唑、三聚茚、异三聚茚、螺三聚茚、螺异三聚茚、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、二苯并噻吩、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并[5,6]喹啉、苯并[6,7]喹啉、苯并[7,8]喹啉、吩噻嗪、吩噁嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、噁唑、苯并噁唑、萘并噁唑、蒽并噁唑、菲并噁唑、异噁唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、六氮杂苯并菲、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、1,5-二氮杂蒽、2,7-二氮杂芘、2,3-二氮杂芘、1,6-二氮杂芘、1,8-二氮杂芘、4,5-二氮杂芘，4,5,9,10-四氮杂苝、吡嗪、吩嗪、吩噁嗪、吩噻嗪、荧红环、萘啶、氮杂咔唑、苯并咔啉、咔啉、菲咯啉、1,2,3-***、1,2,4-***、苯并***、1,2,3-噁二唑、1,2,4-噁二唑、1,2,5-噁二唑、1,3,4-噁二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、吲嗪和苯并噻二唑或者衍生自这些体系的组合的基团。
进一步的，所述的三芳基苯衍生物包括以下CJHM905～CJHM1006所示结构：
/>
/>
/>
/>
本发明的第二目的，提供了一种有机电致发光材料，包括所述的三芳基苯衍生物。
优选的，所述有机电致发光材料包含本发明的化合物的材料具有载流子传输的能力。
本发明的第三目的，提供了一种有机电致发光元件，包括第一电极、第二电极、CPL层和置于所述第一电极、所述第二电极之间的至少一层有机层，所述有机层的至少一层或CPL层包含所述的三芳基苯衍生物。
此时，上述化合物可以单独使用或者两种以上混合使用。
上述一层以上的有机物层可以为空穴注入层、空穴传输层、电子阻挡层、发光层、电子传输层和电子注入层中的任意一种以上。优选地，包含上述化学式(I)的化合物的有机物层可以为CPL层、发光层、空穴注入层、空穴传输层和在空穴传输层上进一步层叠的空穴传输辅助层，更优选地，可以为空穴注入层或CPL层。
根据本发明的有机电致发光元件的发光层可以包含主体材料，优选为磷光主体材料，此时，作为主体材料，可以包含上述化学式(I)的化合物。这样发光层包含上述化学式(I)所表示的化合物的情况下，电子传输能力增加，在发光层中空穴与电子的结合力增强，因此能够提供效率(发光效率和功率效率)、寿命、亮度和驱动电压等优异的有机电致发光元件。此外，本发明的有机电致发光元件的发光层掺杂物可以包含上述化学式(I)的化合物，也可以包含其它的化合物作为掺杂物。
本发明的有机电致发光元件的空穴注入层可以包含空穴材料，此时，作为空穴注入材料，可以包含上述化学式(I)的化合物。这样空穴注入层包含上述化学式(I)所表示的化合物的情况下，较深的分子轨道能级而使空穴注入能力增加，能够降低驱动电压，因此能够提供效率(发光效率和功率效率)、寿命、亮度和驱动电压等优异的有机电致发光元件。其中，在上述有机电致发光元件的阴极层上可以进一步层叠CPL层。这样在CPL层包含上述化学式(I)所表示的化合物的情况下，因高的光折射率而促进光取出效果，因此尤其能够改善蓝色有机电致发光元件的亮度、寿命和驱动电压等。
本发明的有机电致发光元件的结构没有特别限定，作为非限制性例子，可以依次层叠有基板、阳极、空穴注入层、空穴传输层、电子阻挡层、发光层、电子传输层、电子注入层和阴极的结构。其中，在上述阴极层上可以进一步层叠有CPL层，如附图2。此外，本发明的有机电致发光元件的结构可以为电极与有机物层之间***有绝缘层或粘接层的结构。
另一方面，关于本发明的有机电致发光元件，除了上述有机物层中的一层以上包含上述化学式(I)所表示的化合物之外，可以利用本领域中公知的材料和方法来形成有机物层和电极制造。
此外，可用作根据本发明的有机电致发光元件中所包含的阳极的物质没有特别限定，作为非限制性例子，可以使用钒、铬、铜、锌、金、铝等金属或它们的合金；氧化锌、氧化铟、氧化铟锡(ITO)、氧化铟锌(IZO)等金属氧化物；ZnO:Al或SnO2:Sb等金属与氧化物的组合；聚噻吩、聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧)噻吩](PEDT)、聚吡咯和聚苯胺等导电性高分子；以及炭黑等。
可用作根据本发明的有机电致发光元件中所包含的阴极的物质没有特别限定，作为非限制性例子，可以使用镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡或铅等金属或它们的合金；及LiF/Al或LiO2/Al等多层结构物质等。
可用作根据本发明的有机电致发光元件中所包含的基板的物质没有特别限定，作为非限制性例子，可以使用硅片、石英、玻璃板、金属板或塑料膜和片等。
此外优选如下的有机电致发光元件，借助于升华方法施加一个或多个层，其中在真空升华装置中在低于10-5Pa、优选低于10-6Pa的初压下通过气相沉积来施加所述材料。然而，所述初压还可能甚至更低，例如低于10-7Pa。
同样优选如下的有机电致发光元件，借助于有机气相沉积方法或借助于载气升华来施加一个或多个层，其中，在10-5Pa至1Pa之间的压力下施加所述材料。该方法的特别的例子是有机蒸汽喷印方法，其中所述材料通过喷嘴直接施加，并且因此是结构化的。
此外优选如下的有机电致发光元件，从溶液中，例如通过旋涂，或借助于任何所希望的印刷方法例如丝网印刷、柔性版印刷、平版印刷、光引发热成像、热转印、喷墨印刷或喷嘴印刷，来产生一个或多个层。可溶性化合物，例如通过适当的取代获得可溶性化合物。这些方法也特别适于低聚物、树枝状大分子和聚合物。此外可行的是混合方法，其中例如从溶液中施加一个或多个层并且通过气相沉积施加一个或多个另外的层。
这些方法是本领域普通技术人员通常已知的，并且他们可以在不付出创造性劳动的情况下将其应用于包含根据本发明的化合物的有机电致发光元件。
因此，本发明还涉及制造根据本发明的有机电致发光元件的方法，借助于升华方法来施加至少一个层，和/或借助于有机气相沉积方法或借助于载气升华来施加至少一个层，和/或从溶液中通过旋涂或借助于印刷方法来施加至少一个层。
此外，本发明涉及包含至少一种所述的式(I)化合物。如上文关于有机电致发光元件指出的相同优选情况适用于所述本发明的化合物。特别是，所述化合物此外还可优选包含其它化合物。从液相处理根据本发明的式(I)所示化合物，例如通过旋涂或通过印刷方法进行处理，需要根据本发明的化合物的制剂。这些制剂可以例如是溶液、分散体或乳液。出于这个目的，可优选使用两种或更多种溶剂的混合物。合适并且优选的溶剂例如是甲苯，苯甲醚，邻二甲苯、间二甲苯或对二甲苯，苯甲酸甲酯，均三甲苯，萘满，邻二甲氧基苯，四氢呋喃，甲基四氢呋喃，四氢吡喃，氯苯，二噁烷，苯氧基甲苯，特别是3-苯氧基甲苯，(-)-葑酮，1,2,3,5-四甲基苯，1,2,4,5-四甲基苯，1-甲基萘，2-甲基苯并噻唑，2-苯氧基乙醇，2-吡咯烷酮，3-甲基苯甲醚，4-甲基苯甲醚，3,4-二甲基苯甲醚，3,5-二甲基苯甲醚，苯乙酮，α-萜品醇，苯并噻唑，苯甲酸丁酯，异丙苯，环己醇，环己酮，环己基苯，十氢化萘，十二烷基苯，苯甲酸乙酯，茚满，苯甲酸甲酯，1-甲基吡咯烷酮，对甲基异丙基苯，苯***，1,4-二异丙基苯，二苄醚，二乙二醇丁基甲基醚，三乙二醇丁基甲基醚，二乙二醇二丁基醚，三乙二醇二甲基醚，二乙二醇单丁基醚，三丙二醇二甲基醚，四乙二醇二甲基醚，2-异丙基萘，戊苯，己苯，庚苯，辛苯，1,1-双(3,4-二甲基苯基)乙烷，或这些溶剂的混合物。
进一步的，所述的三芳基苯衍生物在有机电致发光元件中用作空穴传输层材料、空穴注入层材料、激子阻挡层材料或CPL层材料。
进一步的，所述有机电致发光元件的空穴注入层或CPL层包含所述的有机电致发光材料。
本发明的第四目的，提供了一种消费型产品，包含所述的有机电致发光元件。
本发明中所述的消费型产品可以是以下产品中的一种：平板显示器、计算机监视器、医疗监视器、电视机、告示牌、用于内部或外部照明和/或发信号的灯、平视显示器、全透明或部分透明的显示器、柔性显示器、激光打印机、电话、蜂窝电话、平板电脑、平板手机、个人数字助理(PDA)、可佩戴装置、膝上型计算机、数码相机、摄像机、取景器、对角线小于2英寸的微型显示器、3-D显示器、虚拟现实或增强现实显示器、交通工具、包含多个平铺在一起的显示器的视频墙、剧院或体育馆屏幕、光疗装置和指示牌。
与现有技术相比，本发明的有益效果为：
(1)本发明所述的三芳基苯衍生物是由芳基乙炔一步合成1,2,4-三芳基取代的苯，制备简单、成本低廉，同时引入大位阻的取代基，使分子不易结晶，提高玻璃化转变温度的同时提高分子的热稳定性；
(2)本发明所述的三芳基苯衍生物非常适合用于有机电致发光元中的空穴注入或空穴传输层中，特别是还适用于CPL层中，这是由于所述的三芳基苯衍生物HOMO能级较低，利于空穴的注入；光折射率大、但吸光系数小，因此利于光的取出效率；
(3)本发明所述的三芳基苯衍生物用作空穴注入层材料时，具有非常高的效率和长寿命，尤其是所述衍生物与其它掺杂材料，例如p型掺杂物，一起用作空穴注入材料时特别适用这点；
(4)所述的衍生物用于有机电致发光元件中时，具有较高的效率，并且在使用和低工作电压的情况下导致陡峭的电流-电压曲线，本发明所述的衍生物具有高的热稳定性，并且能够在不分解和没有残余物的情况下进行升华，另外具有高的氧化稳定性，对于衍生物的处理和对于溶液的贮存稳定性具有积极的效果。
附图说明
为了更清楚地说明本发明实施例或现有技术中的技术方案，下面将对实施例或现有技术描述中所需要使用的附图作简单地介绍，显而易见地，下面描述中的附图仅仅是本发明的一些实施例，对于本领域普通技术人员来讲，在不付出创造性劳动的前提下，还可以根据这些附图获得其他的附图。
图1是本发明的有机电致发光元件的一个含有CPL层的示意图；
图2是本发明的有机电致发光元件的一个不含空穴阻挡层的示意图。
附图标记
101-基板，102-阳极层，103-空穴注入层，104-空穴传输层，105-电子阻挡层，106-发光层，107-空穴阻挡层，108-电子传输层，109-电子注入层，110-阴极层，111-CPL层。
具体实施方式
为使本发明的目的、技术方案和优点更加清楚，下面将对本发明的技术方案进行详细的描述。显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有做出创造性劳动的前提下所得到的所有其它实施方式，都属于本发明所保护的范围。
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元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材料及元件进行性能测试的测试仪器及方法如下：
OLED元件性能检测条件：
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；
寿命测试：使用LTS-1004AC寿命测试装置。
本发明所述的三芳基苯衍生物的合成路线，包括如下步骤：
其中X选自氢、氯、溴、碘或OTf；R、Ar和n的含义如上文所定义。
实施例1
化合物A1的制备方法：
110.0mmol的对氯苯乙炔溶解于80.0mL的乙腈中，在氮气保护下，加入3.3mmol的碘化钴、3.3mmol的叔丁醇钾和11.0mmol的频那醇硼烷，升温至30℃搅拌反应12小时，减压浓缩干燥，用硅胶柱分离纯化，得到化合物A1，白色固体，收率：62％，MS(TOF)m/z＝408.0233[M+]。
参照上述A1的合成方法，制备以下化合物：
/>
/>
/>
/>
/>
/>
/>
/>
/>
实施例2
化合物CJHM910的制备：
36.0mmol的N-苯基-[1,1'-联苯基]-4-胺，10.0mmol的化合物A1、45.0mmol的叔丁醇钠，再加入0.05mmol的Pd2(dba)3CHCl3催化剂、0.1mL的10％三叔丁基磷甲苯溶液和80mL的二甲苯，在氮气保护下，升温至110℃搅拌反应12小时，冷却到室温，加入50mL的水稀释，用二氯甲烷萃取，有机相干燥，过滤，滤液减压浓缩干燥，用硅胶柱分离纯化，得到化合物CJHM910，白色固体，收率76％，MS(TOF)m/z＝1036.4644[M+H]。
参照上述类似的合成方法，制备以下化合物：
/>
/>
实施例3
化合物CJHM956的制备：
10.0mmol的A2，35.0mmol的3-吡啶硼酸、60.0mmol的碳酸钾，再加入0.01mmol的Pd132催化剂和40mL的甲苯、20mL的乙醇以及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，加入50mL的水稀释，用乙酸乙酯萃取，有机相干燥，过滤，滤液减压浓缩干燥，用硅胶柱分离纯化，得到化合物CJHM956，收率87％，MS(TOF)m/z＝538.2301[M+H]。
参照上述类似的合成方法，制备以下化合物：
实施例4
化合物CJHM999的制备：
20.0mmol的A10溶于80mL的二氯甲烷，加入40mL的30％双氧水，升温回流搅拌反应10小时，冷却到室温，加入100mL的水稀释，用二氯甲烷萃取，有机相干燥，过滤，滤液减压浓缩干，用硅胶柱分离纯化，得到化合物CJHM999，白色固体，收率100％，MS(TOF)m/z＝907.2678[M+H]。
实施例5
化合物CJHM1003的制备方法，包括以下步骤：
第一步：化合物A11的制备
在氮气保护下，20.0mmol的5,10-二苯基-5,10-二氢二苯并[b,e][1,4]氮杂硼烷(CAS:1347741-58-5)溶于50mL干燥的THF，降温至-78℃，滴加入22mmol的0.5M乙炔基溴化镁THF溶液，升到室温搅拌反应1小时，加入5mL的甲醇，减压浓缩干燥，再加入150mL的甲醇搅拌溶解，加入22mmol的四甲基氯化铵固体，室温搅拌反应24小时，过滤，滤饼用甲醇洗，得到化合物A11，收率46％。
第二步：化合物CJHM1003的制备
10.0mmol的A11溶解于60.0mL的乙腈中，在氮气保护下，加入0.2mmol的碘化钴、0.1mmol的叔丁醇钾和1.0mmol的频那醇硼烷，升温至30℃搅拌反应12小时，滴加入40mL的2N稀盐酸，用二氯甲烷萃取，收集有机相用水洗，干燥，减压浓缩干，用硅胶柱分离纯化，得到化合物CJHM1003，白色固体，收率：78％，MS(TOF)m/z＝838.3754[M+H]。
参照上述类似的合成方法，制备以下化合物：
本发明提供的OLED元件如图1和图2所示，下面以图2所示的OLED元件结构为例，制备本发明提供的OLED元件。图2中，101是基板，102是阳极层，103是空穴注入层，104是空穴传输层，105是电子阻挡层，106是发光层，108是电子传输层，109是电子注入层，110是阴极层，111是CPL层。
对比例1
使用下述的化合物式C作为空穴注入层的掺杂材料、式E作为空穴注入层主体的材料、式D作为空穴传输层材料、式H作为电子阻挡层材料、式A作为发光层的主体材料、式B作为发光层的掺杂材料、式G作为电子传输层的掺杂材料、LiQ作为电子传输层的主体材料、式F作为CPL层的材料，如下所述的制备有机电致发光元件。
将Al/E+C(3％)/>/D/>/H/>/A+B(3％)/>/LiQ+G(30％)/>/LiF/>/Mg+Ag(50％)/>/F/>依次采用DOV公司制造的EL蒸镀机蒸镀到ITO玻璃上制作发光元件，制得对比例1的有机电致发光元件。
实施例6
按照对比例1中有机电致发光元件制备方法，将所述的化合物E或F替换为本发明的化合物CJHM905～CJHM1006，除此之外，采用同样的方法制作有机电致发光元件：ITO/Al/(本发明的化合物式I)+C(3％)/>/D/>/H/>/A+B(3％)/>/LiQ+G(30％)/>/LiF/>/Mg+Ag(50％)/>/F/>或ITO/Al/>/E+C(3％)/>/D/>/H/>/A+B(3％)/>/LiQ+G(30％)/>/LiF/>/Mg+Ag(50％)/>/(本发明的化合物式I)/>
所得元件的性能是在元件亮度在1000尼特条下的测试结果，并且电压、外量子效率(EQE)、电流效率(LE)和衰减寿命LT95％的数据是相对于对比例1元件归一化，所得结果列于表1中。
表1元件性能检测结果
/>
/>
/>
/>
/>
由上表可知，本发明的三芳基苯衍生物用作空穴注入层主体材料制备成的OLED元件驱动电压低，效率较高，色纯度较好，而且在元件发光亮度初始为1000尼特的条件下，元件LT95％寿命有大幅度提升。使用本发明的三芳基苯衍生物用CPL材料制备的OLED元件出光效率更高，色域增大，元件寿命衰更为平缓。
以上所述，仅为本发明的具体实施方式，但本发明的保护范围并不局限于此，任何熟悉本技术领域的技术人员在本发明揭露的技术范围内，可轻易想到变化或替换，都应涵盖在本发明的保护范围之内。因此，本发明的保护范围应以所述权利要求的保护范围为准。

Claims (8)

1.一种三芳基苯衍生物，其特征在于，三芳基苯衍生物选自如下群组：
其中，T选自O、S、CR3R4、NR5或SiR3R4；
其中，R3、R4、R5在每次出现时相同或不同地选自氢原子、氘原子、氟原子、腈基、具有C1～C40的直链烷基、具有C3～C40的支链或环状的烷基、具有5至60个碳原子的芳基或具有2至60个碳原子的杂芳基组成的组；
R各自独立地选自氢原子、氘原子、卤素原子、腈基、具有C1～C40的直链烷基、具有C1～C40的直链杂烷基、具有C3～C40的支链或环状的烷基、具有C3～C40的支链或环状的杂烷基、具有C2～C40的烯基或炔基、具有5至60个碳原子的芳基或具有2至60个碳原子的杂芳基或NR1R2组成的群组，并且R不全部为氢或氘；
R1、R2各自相同或者不同，选自由取代或未取代的C5～C60的芳基、取代或未取代的C5～C60的芳胺基、取代或未取代的C5～C60的芳硼基、取代或未取代的C5～C60的芳磷基、取代或未取代的C2～C60的杂芳基组成的群组，R1和R2可以任选地接合或稠合形成另外的一个或多个取代或未取代的环，在所形成的环中含有或不含有一个或多个杂原子N、P、B、O、S、P＝O、或含有或不含有一个或多个CR3R4、SiR3R4。
2.根据权利要求1所述的三芳基苯衍生物，其特征在于，所述基团R1和R2在每次出现时相同或不同地选自由式(2)～(33)的基团组成的群组：
其中，R3、R4、R5在每次出现时相同或不同地选自氢原子、氘原子、氟原子、腈基、具有C1～C40的直链烷基、具有C3～C40的支链或环状的烷基、具有5至60个碳原子的芳基或具有2至60个碳原子的杂芳基组成的组；
其中，虚线键指示与N连接的位置。
3.根据权利要求1-2任意一项所述的三芳基苯衍生物，其特征在于，所述化合物包括以下CJHM905～CJHM1006所示结构：
4.一种有机电致发光材料，其特征在于，包括权利要求1-3任意一项所述的三芳基苯衍生物。
5.一种有机电致发光元件，包括第一电极、第二电极、CPL层和置于所述第一电极、所述第二电极之间的至少一层有机层，其特征在于，所述有机层的至少一层或CPL层包含权利要求1-3任意一项所述的三芳基苯衍生物。
6.根据权利要求5所述的有机电致发光元件，其特征在于，所述的三芳基苯衍生物在有机电致发光元件中用作空穴传输层材料、空穴注入层材料、激子阻挡层材料、或CPL层材料。
7.根据权利要求6所述的有机电致发光元件，其特征在于，所述有机电致发光元件的空穴注入层或CPL层包含权利要求6所述的材料。
8.一种消费型产品，其特征在于，包含权利要求6或7所述的有机电致发光元件。
CN202111282565.XA 2021-11-01 2021-11-01 一种三芳基苯衍生物、发光材料、发光元件及消费型产品 Active CN114014742B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202111282565.XA CN114014742B (zh) 2021-11-01 2021-11-01 一种三芳基苯衍生物、发光材料、发光元件及消费型产品

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202111282565.XA CN114014742B (zh) 2021-11-01 2021-11-01 一种三芳基苯衍生物、发光材料、发光元件及消费型产品

Publications (2)

Publication Number Publication Date
CN114014742A CN114014742A (zh) 2022-02-08
CN114014742B true CN114014742B (zh) 2024-05-10

Family

ID=80059514

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202111282565.XA Active CN114014742B (zh) 2021-11-01 2021-11-01 一种三芳基苯衍生物、发光材料、发光元件及消费型产品

Country Status (1)

Country Link
CN (1) CN114014742B (zh)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023172112A1 (ko) * 2022-03-10 2023-09-14 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
WO2024013275A1 (de) * 2022-07-15 2024-01-18 Merck Patent Gmbh Materialien für elektronische vorrichtungen

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004253298A (ja) * 2003-02-21 2004-09-09 Konica Minolta Holdings Inc 白色発光有機エレクトロルミネッセンス素子
JP2006156999A (ja) * 2004-11-08 2006-06-15 Fuji Photo Film Co Ltd 有機電界発光素子
CN1894199A (zh) * 2003-11-14 2007-01-10 住友化学株式会社 卤代双二芳基氨基多环芳族化合物及其聚合物
CN101287713A (zh) * 2005-11-30 2008-10-15 三菱化学株式会社 有机化合物、电荷传输材料、电荷传输材料用组合物和有机电致发光元件
JP2009182088A (ja) * 2008-01-30 2009-08-13 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置
CN108976138A (zh) * 2018-07-31 2018-12-11 湖南工业大学 一种功能三胺单体及其制备方法和应用
CN109161018A (zh) * 2018-07-31 2019-01-08 湖南工业大学 一种芳香族超支化聚酰亚胺及其制备方法和用途
JP2020040912A (ja) * 2018-09-12 2020-03-19 コニカミノルタ株式会社 含窒素複素環化合物の製造方法
CN113429302A (zh) * 2021-08-27 2021-09-24 北京八亿时空液晶科技股份有限公司 一种萘并芴衍生物、发光材料、发光元件及消费型产品

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004253298A (ja) * 2003-02-21 2004-09-09 Konica Minolta Holdings Inc 白色発光有機エレクトロルミネッセンス素子
CN1894199A (zh) * 2003-11-14 2007-01-10 住友化学株式会社 卤代双二芳基氨基多环芳族化合物及其聚合物
JP2006156999A (ja) * 2004-11-08 2006-06-15 Fuji Photo Film Co Ltd 有機電界発光素子
CN101287713A (zh) * 2005-11-30 2008-10-15 三菱化学株式会社 有机化合物、电荷传输材料、电荷传输材料用组合物和有机电致发光元件
JP2009182088A (ja) * 2008-01-30 2009-08-13 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子、表示装置及び照明装置
CN108976138A (zh) * 2018-07-31 2018-12-11 湖南工业大学 一种功能三胺单体及其制备方法和应用
CN109161018A (zh) * 2018-07-31 2019-01-08 湖南工业大学 一种芳香族超支化聚酰亚胺及其制备方法和用途
JP2020040912A (ja) * 2018-09-12 2020-03-19 コニカミノルタ株式会社 含窒素複素環化合物の製造方法
CN113429302A (zh) * 2021-08-27 2021-09-24 北京八亿时空液晶科技股份有限公司 一种萘并芴衍生物、发光材料、发光元件及消费型产品

Also Published As

Publication number Publication date
CN114014742A (zh) 2022-02-08

Similar Documents

Publication Publication Date Title
TWI745395B (zh) 有機電致發光裝置用之材料
CN113387818B (zh) 化合物和包含该化合物的有机电致发光装置和电子设备
CN114591328B (zh) 一种咔唑衍生物及其应用
CN113429302B (zh) 一种萘并芴衍生物、发光材料、发光元件及消费型产品
CN112321598A (zh) 一种咔唑衍生物及其应用
CN114014742B (zh) 一种三芳基苯衍生物、发光材料、发光元件及消费型产品
CN113072560B (zh) 一种咔唑衍生物及其应用
CN113912471B (zh) 蒽衍生物、有机电致发光材料、发光装置及消费型产品
CN113735853B (zh) 一种有机金属配合物以及包含该金属配合物的电致发光元件和化合物配方
CN114044785A (zh) 一种含硼化合物和有机电致发光元件、有机电致发光材料
CN113024444A (zh) 一种化合物以及含有该化合物的有机电致发光元件用材料、有机电致发光装置和电子设备
CN113264944A (zh) 一种有机化合物、有机电致发光材料及其装置
CN112812108B (zh) 化合物及包含该化合物的有机电致发光装置
WO2023138254A1 (zh) 杂环化合物、有机电致发光材料及元件
WO2023082808A1 (zh) 一种四氮杂荧蒽化合物及其应用
CN114907179B (zh) 蒽衍生物及使用其的有机电致发光材料、发光装置和消费型产品
CN114605411B (zh) 一种吖啶衍生物及其应用
CN113563344B (zh) 咔唑衍生物、有机电致发光材料、发光元件及消费型产品
CN113563312B (zh) 一种吡咯衍生物、有机电致发光材料、发光元件及消费型产品
CN113387821A (zh) 芴类化合物、有机电致发光元件及消费型产品
CN114349798A (zh) 一种金属配合物与应用及消费型产品
CN111819169B (zh) 用于有机电致发光器件的材料
CN113429393B (zh) 蒽并吲哚衍生物、有机电致发光元件用材料、发光元件及消费型产品
CN114560872B (zh) 一种杂环咪唑化合物及其应用
CN113912636B (zh) 含硅杂环化合物和含有该化合物的有机电致发光元件

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
GR01 Patent grant
GR01 Patent grant