CN107011248B - 化合物及其有机电子装置 - Google Patents

化合物及其有机电子装置 Download PDF

Info

Publication number
CN107011248B
CN107011248B CN201710061133.3A CN201710061133A CN107011248B CN 107011248 B CN107011248 B CN 107011248B CN 201710061133 A CN201710061133 A CN 201710061133A CN 107011248 B CN107011248 B CN 107011248B
Authority
CN
China
Prior art keywords
group
layer
organic
compound
electrode
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.)
Expired - Fee Related
Application number
CN201710061133.3A
Other languages
English (en)
Other versions
CN107011248A (zh
Inventor
廖良玓
吴蕙玲
谢淑珠
陈济中
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 Nichem Fine Chemical Co Ltd
Original Assignee
Shanghai Nichem Fine Chemical 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 Nichem Fine Chemical Co Ltd filed Critical Shanghai Nichem Fine Chemical Co Ltd
Publication of CN107011248A publication Critical patent/CN107011248A/zh
Application granted granted Critical
Publication of CN107011248B publication Critical patent/CN107011248B/zh
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • 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 Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—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
    • 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
    • C07C211/61—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
    • 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
    • C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups 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
    • C07D213/06—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
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent 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
    • C07D213/24—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
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom 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
    • 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
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • 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
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • C07D313/02—Seven-membered rings
    • C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • 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
    • 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
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/625—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing at least one aromatic ring having 7 or more carbon atoms, e.g. azulene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/653—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
    • 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
    • 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
    • C07C2603/93—Spiro compounds
    • C07C2603/95—Spiro compounds containing "not free" spiro atoms
    • C07C2603/98—Spiro compounds containing "not free" spiro atoms containing at least one ring with more than six ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/93—Spiro compounds
    • C07C2603/95—Spiro compounds containing "not free" spiro atoms
    • C07C2603/98—Spiro compounds containing "not free" spiro atoms containing at least one ring with more than six ring members
    • C07C2603/99—Spiro compounds containing "not free" spiro atoms containing at least one ring with more than six ring members containing eight-membered rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—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
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

本发明提供一种化合物及其有机电子装置，化合物如下式(I)所示，G1至G4之一为碳数小于或等于60且具有至少一个氮原子的杂芳基、具有至少一个官能基的环烷基、杂环烷基、芳香基、芳氧基、芳硅基或芳硼基；或者为碳数小于或等于40且具有至少一个官能基的烷基、烯基、炔基、烷氧基、硅烷基、硼烷基、膦基或氧膦基；该官能基选自由氰基、硝基、氟基和氯基所构成的群组；G1至G4中其他者和G5分别独立为经取代或未经取代的上述基团；h、i、j、k和l分别独立为1至4的整数。
Figure DDA0001219395960000011

Description

化合物及其有机电子装置
技术领域
本发明是关于一种新型化合物以及一种使用其的有机电子装置，尤其是一种用于电子传输层的新型化合物以及使用其的有机电子装置。
背景技术
随着科技的进步，各种使用有机材料制成的有机电子装置蓬勃发展，常见的有机电子装置如有机发光二极管(organic light emitting device，OLED)、有机光敏晶体管(organic phototransistor)、有机光伏打电池(organic photovoltaic cell)和有机光侦测器(organic photodetector)。
OLED最初是由伊士曼柯达公司(Eastman Kodak)所发明并提出，伊士曼柯达公司的邓青云博士和Steven Van Slyke以真空蒸镀法(vacuum evaporation method)在形成有有机芳香二元胺电洞传输层的透明氧化铟锡(indium tin oxide，ITO)玻璃上沉积一电子传输材料{例如三(8-羟基喹啉)铝[tris(8-hydroxyquinoline)aluminum(III)，简称为Alq3]}；再在电子传输层上沉积一金属电极，即可完成OLED的制作。OLED因兼具反应速率快、质轻、薄形化、广视角、亮度高、对比高、无需设置背光源以及低耗能的优点，因此备受关注，但OLED仍具有低效率和寿命短的问题。
为了克服低效率的问题，其中一种改善方式为在阴极和阳极间设置中间层，请参阅图1所示，改良的OLED依序设置有一基板11、一阳极12、一电洞注入层13(hole injectionlayer，HIL)、一电洞传输层14(hole transport layer，HTL)、一发光层15(an emittinglayer，EL)、一电子传输层16(electron transport layer，ETL)、一电子注入层17(electron injection layer，EIL)和一阴极18。当在阳极12和阴极18施加一电压时，由阳极12射出的电洞会穿过HIL和HTL并移动至EL，而由阴极18射出的电子会穿过EIL和ETL移动至EL，使电洞和电子在EL层重组成激子(exciton)，当激子由激发态衰退返回基态时即可产生光线。
另一改善方式为改良OLED中ETL的材料，使电子传输材料展现出电洞阻挡能力，传统的电子传输材料包括3,3′-[5′-[3-(3-吡啶基)苯基][1,1′:3′,1″-三联苯]-3,3″-二基]二吡啶{(3,3′-[5′-[3-(3-pyridinyl)phenyl][1,1′:3′,1″-terphenyl]-3,3″-diyl]bispyridine，TmPyPb}、1,3,5-三(1-苯基-1H-苯并咪唑-2-基)苯[1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene，TPBi]、三(2,4,6-三甲基-3-(3-吡啶基)苯基)硼烷[tris(2,4,6-trimethyl-3-(pyridin-3-yl)phenyl)borane，3TPYMB]、1,3-二(3,5-二吡啶-3-基-苯基)苯[1,3-bis(3,5-dipyrid-3-yl-phenyl)benzene，BmPyPb]和9,10-二(3-(3-吡啶基)苯基)蒽[9,10-bis(3-(pyridin-3-yl)phenyl)anthracene，DPyPA]。
然而，即使使用了所述电子传输材料，OLED的电流效率仍具有可改善的空间，因此，本发明提供了一种新型化合物以克服传统低电流效率的问题。
发明内容
本发明的目的为提供一种新型化合物，其可用于有机电子装置。
本发明的另一目的为提供一种使用该新型化合物的有机电子装置，以降低有机电子装置的驱动电压。
此外，本发明的另一目的为提供一种使用该新型化合物的有机电子装置，以提升有机电子装置的效率。
为达上述目的，本发明的新型化合物具有式(I)：
Figure GDA0002397318850000021
在式(I)中，G1至G4之一选自由下列所构成的群组：具有至少一个氮原子且碳数为3至60的杂芳基、具有至少一个官能基且碳数为1至40的烷基、具有至少一个官能基且碳数为2至40的烯基、具有至少一个官能基且碳数为2至40的炔基、具有至少一个官能基且碳数为3至60的环烷基、具有至少一个官能基且碳数为3至60的杂环烷基、具有至少一个官能基且碳数为1至40的烷氧基、具有至少一个官能基且碳数为6至60的芳香基、具有至少一个官能基且碳数为6至60的芳氧基(aryloxy group)、具有至少一个官能基且碳数为1至40的硅烷基(alkylsilyl group)、具有至少一个官能基且碳数为6至60的芳硅基(arylsilyl group)、具有至少一个官能基且碳数为1至40的硼烷基(alkylboron)、具有至少一个官能基且碳数为6至60的芳硼基(arylboron group)、具有至少一个官能基且碳数为1至40的膦基(phosphine group)和具有至少一个官能基且碳数为1至40的氧膦基(phosphine oxidegroup)；
该官能基选自由氰基、硝基、三氟甲基(trifluoromethyl group)、氟基和氯基所构成的群组；
G1至G4中其他者和G5分别独立选自由下列所构成的群组：氢原子、氘原子、卤基、氰基、硝基、三氟甲基、经取代或未经取代且碳数为1至40的烷基、经取代或未经取代且碳数为2至40的烯基、经取代或未经取代且碳数为2至40的炔基、经取代或未经取代且碳数为3至60的环烷基、经取代或未经取代且碳数为3至60的杂环烷基、经取代或未经取代且碳数为1至40的烷氧基、经取代或未经取代且碳数为6至60的芳香基、经取代或未经取代且碳数为3至60的杂芳基、经取代或未经取代且碳数为6至60的芳氧基、经取代或未经取代且碳数为1至40的硅烷基、经取代或未经取代且碳数为6至60的芳硅基、经取代或未经取代且碳数为1至40的硼烷基、经取代或未经取代且碳数为6至60的芳硼基、经取代或未经取代且碳数为1至40的膦基和经取代或未经取代且碳数为1至40的氧膦基；
式(I)中，h、i、j、k和l分别独立为1至4的整数，即h、i、j、k和l可分别为1、2、3或4。
优选地，该化合物表示如下式(I-I)至(I-XV)但不限于：
Figure GDA0002397318850000031
Figure GDA0002397318850000041
在式(I)中，j、k和l分别独立为1至3的整数。
优选地，h、i、j、k和l分别独立为1或2，且h、i、j、k和l的总和小于或等于6。
优选地，其中G1可与G2相同或相异，其中G3可与G4相同或相异。
优选地，G3至G5可分别独立选自由氢原子、氘原子、卤基、未经取代且碳数为1至12的烷基、未经取代且碳数为2至12的烯基和未经取代且碳数为2至12的炔基所构成的群组。
优选地，所述具有至少一个氮原子且碳数为3至60的杂芳基可选自由下列所构成的群组：
Figure GDA0002397318850000042
Figure GDA0002397318850000051
其中，R1至R7分别独立选自由下列所构成的群组：氢原子、氘原子、卤基、氰基、硝基、三氟甲基、碳数为1至12的烷基、碳数为2至12的烯基、碳数为2至12的炔基、碳数为3至30的环烷基、碳数为3至30的杂环烷基、碳数为6至30的芳香基、碳数为3至20的杂芳基、碳数为1至40的烷氧基、碳数为6至30的芳氧基、碳数为1至40的硅烷基、碳数为6至30的芳硅基、碳数为1至40的硼烷基、碳数为6至30的芳硼基、碳数为1至30的膦基和碳数为1至30的氧膦基；
其中n为1至4的整数；m为1至3的整数。
优选地，该R1至R7各分别独立为，但不限于：苯基、萘基(napthyl group)、吡啶基(pyridine group)、嘧啶基(pyrimidine group)、吡嗪基(pyrazine group)、哒嗪基(pyridazine group)、氰基、硝基、三氟甲基、氟基、联苯基(biphenyl group)、萘苯基(phenylnapthyl group)、吡啶苯基(phenylpyridine group)、嘧啶苯基(phenylpyrimidine group)、吡嗪苯基(phenylpyrazine group)、哒嗪苯基(phenylpyridazine group)、氰苯基(cyanophenyl group)、硝苯基(nitrophenyl group)或三氟甲基苯基(trifluoromethylphenyl group)。
优选地，前述“具有至少一个氮原子且碳数为3至60的杂芳基”可选自以下构成的群组：
Figure GDA0002397318850000052
其中，R1和R2分别为苯基、萘基、吡啶基、嘧啶基、吡嗪基、哒嗪基、氰基、硝基、三氟甲基、氟基、联苯基、萘苯基、吡啶苯基、嘧啶苯基、吡嗪苯基和哒嗪苯基、氰苯基、硝苯基或三氟甲基苯基。优选地，R1和R2分别为吡啶基、嘧啶基、吡嗪基、哒嗪基、氰基、硝基、三氟甲基、氟基、吡啶苯基、嘧啶苯基、吡嗪苯基和哒嗪苯基、氰苯基、硝苯基或三氟甲基苯基。在本发明中，R1可与R2相同或不同。
在本发明的一实施例中，G1和/或G2分别为主架构为吡啶基的基团，例如下述基团，但不限于：
Figure GDA0002397318850000061
在另一实施例中，G1和/或G2分别为主架构为嘧啶基的基团，例如下述基团，但不限于：
Figure GDA0002397318850000062
在另一实施例中，G1和/或G2分别为主架构为苯并咪唑基(benzimidazole group)的基团，例如下述基团，但不限于：
Figure GDA0002397318850000063
在另一实施例中，G1和/或G2分别为主架构为嘧啶基的基团，例如下述基团，但不限于：
Figure GDA0002397318850000064
Figure GDA0002397318850000071
Figure GDA0002397318850000081
在另一实施例中，G1和/或G2分别为主架构为三嗪基(triazine group)的基团，例如下述基团，但不限于：
Figure GDA0002397318850000082
Figure GDA0002397318850000091
优选地，前述“具有至少一个氮原子且碳数为3至60的杂芳基”可以为一个经二苯基取代的三嗪基(triazine group)、经二吡啶基取代的三嗪基、经二嘧啶基取代的三嗪基、经二吡嗪基取代的三嗪基、经二哒嗪基取代的三嗪基、经二吡啶苯基取代的三嗪基、经二嘧啶苯基取代的三嗪基、经二吡嗪苯基取代的三嗪基、经二哒嗪苯基取代的三嗪基。
优选地，该“具有至少一个官能基且碳数为6至60的芳香基”选自由下列所构成的群组：
Figure GDA0002397318850000092
其中R1选自由下列所构成的群组：氢原子、氘原子、卤基、氰基、硝基、三氟甲基、碳数为1至12的烷基、碳数为2至12的烯基、碳数为2至12的炔基、碳数为3至30的环烷基、碳数为3至30的杂环烷基、碳数为6至30的芳香基、碳数为3至20的杂芳基、碳数为1至40的烷氧基、碳数为6至30的芳氧基、碳数为1至40的硅烷基、碳数为6至30的芳硅基、碳数为1至40的硼烷基、碳数为6至30的芳硼基、碳数为1至30的膦基和碳数为1至30的氧膦基；
其中o为0至4的整数；p为1至5的整数；o和p的总和小于或等于5。
优选地，该新型化合物可以为以下化合物，但并非仅限于此：
Figure GDA0002397318850000101
Figure GDA0002397318850000111
Figure GDA0002397318850000121
Figure GDA0002397318850000131
Figure GDA0002397318850000141
Figure GDA0002397318850000151
Figure GDA0002397318850000161
Figure GDA0002397318850000171
Figure GDA0002397318850000181
Figure GDA0002397318850000191
Figure GDA0002397318850000201
Figure GDA0002397318850000211
Figure GDA0002397318850000221
Figure GDA0002397318850000231
Figure GDA0002397318850000241
Figure GDA0002397318850000251
Figure GDA0002397318850000261
Figure GDA0002397318850000271
Figure GDA0002397318850000281
本发明还提供一种有机电子装置，其包括第一电极、第二电极和设置在该第一电极和该第二电极间的有机层，该有机层包括所述化合物。
优选地，该有机电子装置为有机发光二极管(OLED)。优选地，该新型化合物可被使用于该电子传输层或电洞阻挡层。
具体而言，该有机发光二极管包括电洞注入层、电洞传输层、发光层、电子传输层和电子注入层；该电洞注入层形成于该第一电极上；该电洞传输层形成于该电洞注入层上；该发光层形成于该电洞传输层上；该电子传输层形成于该发光层上，该有机层为该电子传输层；该电子注入层形成于该电子传输层和该第二电极之间。
优选地，该电洞注入层可以为双层结构，即该OLED具有第一电洞注入层和第二电洞注入层，第一电洞注入层和第二电洞注入层设置于第一电极和电洞传输层之间。
相同地，该电洞传输层还可以为双层结构，即该OLED具有第一电洞注入层和第二电洞注入层，第一电洞注入层和第二电洞注入层设置于电洞注入层的双层结构与发光层之间。
优选地，该电子传输层是由该新型化合物(如所述化合物I至CCXCIII)所制成，本发明的OLED相较于商业上的OLED具有较佳的电流效率，其中商业上的OLED使用的化合物如2-{4-[9,10-二(2-萘基)-2-蒽基]苯基}-1-苯基-1H-苯并[d]咪唑{2-[4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl]-1-phenyl-1H-benzo[d]imidazole}、二(2-甲基-8-羟基喹啉)(p-苯基苯酚)铝[bis(2-methyl-8-quinolinolato)(p-phenylphenolato)aluminum]或2-(4-联苯基)-5-(叔丁苯基)-1,3,4-恶二唑[2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole)，PBD]。
优选地，该OLED包括电洞阻挡层，该电洞阻挡层形成于电子传输层和发光层之间，可防止电洞由发光层移动至电子传输层，所述电洞阻挡层可由前述化合物、2,9-二甲基-4,7-联苯基-1,10-邻二氮杂菲(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline，BCP)或2,3,5,6-四甲基-1-苯基-1,4-邻苯二甲酰亚胺[2,3,5,6-tetramethyl-phenyl-1,4-(bis-phthalimide)，TMPP]所形成，但并不仅限于此。
优选地，该OLED包括一电子阻挡层，该电子阻挡层形成于电洞传输层和发光层之间，可防止电子由发光层移动至电洞传输层，所述电子阻挡层可由4,4'-二(9-咔唑)联苯[9,9'-(1,1'-biphenyl)-4,4'-diylbis-9H-carbazole，CBP]或4,4',4”-三(N-咔唑基)三苯胺[4,4',4”-tri(N-carbazolyl)-triphenylamine，TCTA]所形成，但并不仅限于此。
当OLED设置有电洞阻挡层或电子阻挡层时，本发明的OLED相较于传统的OLED具有较高的发光效率。
所述第一和第二电洞传输层可由N,N'-(4,4’-二联苯基)二(N1-(1-萘基))-N,N'-联苯基苯-1,4-二胺[N1,N1’-(biphenyl-4,4'-diyl)bis(N1-(naphthalen-1-yl)-N4,N4’-diphenylbenzene-1,4-diamine)]或N,N'-二联苯基-N,N'-二(1-萘基)-1,1'-联苯-4,4'-二胺[N4,N4'-di(naphthalen-1-yl)-N4,N4’-diphenylbiphenyl-4,4'-diamine，NPB]所制成。
所述第一和第二电洞注入层可由聚苯胺或聚乙烯基二氧噻吩(polyethylenedioxythiophene)所制成，但并不仅限于此。
所述发光层可由发光材料制成，该发光材料包括主发光体(host)和掺杂物(dopant)，其中主发光体的材料例如9-[4-(1-萘基)苯基]-10-(2-萘基)蒽[9-(4-(naphthalen-1-yl)phenyl)-10-(naphthalen-2-yl)anthracene]，但不限于此。
针对红光OLED，发光层中的掺杂物可以为具有苝(perylene)配位基、荧蒽(fluoranthene)配位基或二茚并(periflanthene)配位基的二价铱有机金属化合物，但并不仅限于此。针对绿光OLED，发光层中的掺杂物可以为二氨基芴(diaminoflourenes)、蒽二胺(diaminoanthracenes)或具有苯基吡啶(phenylpyridine)配位基的二价铱有机金属化合物，但并不仅限于此。针对蓝光OLED，发光层中的掺杂物可以为二氨基芴、蒽二胺、芘二胺(diaminopyrenes)或具有苯基吡啶配位基的二价铱有机金属化合物，但并不仅限于此。通过不同的主发光体材料，OLED可产生红光、绿光或蓝光的光线。
所述电子注入层可由电子注入材料制成，例如8-氧代萘-1-基锂[(8-oxidonaphthalen-1-yl)lithium(II)]，但不限于此。
所述第一电极可以为氧化铟锡电极(indium-doped tin oxide electrode)，但并不仅限于此。
所述第二电极的功函数(work function)低于第一电极的功函数。因此，第二电极可以是但不局限于铝电极、铟电极或镁电极。
本发明的其他目的、功效和技术特征，会以图式、实施例和比较例进行更详细的说明。
附图说明
图1为OLED的侧视剖面图。其中：
11 基板 12 阳极
13 电洞注入层 14 电洞传输层
15 发光层 16 电子传输层
17 电子注入层 18 阴极。
图2至图15分别为化合物I至化合物XIV的氢核磁共振光谱图。
具体实施方式
以下列举数个实施例作为例示说明本发明的化合物及其有机电子装置的实施方式，以突显本发明相较于现有技术的差异；本领域技术人员可通过本说明书的内容轻易了解本发明所能达成的优点与功效，并且在不悖离本发明的精神下进行各种修饰与变更，以施行或应用本发明的内容。
中间物A1的合成
中间物A1(Intermediate A1)用于制备一种新型化合物，中间物A1可通过下述合成机制A1中的步骤进行合成。
Figure GDA0002397318850000311
步骤1：合成中间物A1-1
混合86克(1.0当量)的3-溴二苯并[a,d]环庚烯-5-酮(3-bromodibenzo[a,d]cyclohepten-5-one)、106克(2.0当量)的N-溴代丁二酰亚胺(N-bromosuccinimide，NBS)和0.7克(0.01当量)的过氧化苯甲酰(benzyl peroxide)在430毫升的四氯化碳(carbontetrachloride，CCl4)中，并加热至85℃进行反应，在反应的过程中以高效液相色谱仪(high performance liquid chromatography，HPLC)进行监测；当反应完成后，过滤分离反应产生的沉淀物，并以甲醇冲洗再以再结晶的方式纯化，接着经浓缩和干燥后，获得123克的白色固体产物，产率为92.3％。
经场脱附质谱(field desorption mass spectroscopy，FD-MS)分析确定，白色固体产物即为中间物A1-1。FD-MS分析结果：C15H9Br3O，理论值444.94，检测值444.94。
步骤2：合成中间物A1-2
称取116.0克(1.0当量)的中间物A1-1，使中间物A1-1溶解于960毫升呋喃(furan)和四氢呋喃(tetrahydrofuran，THF)体积比为2：1的混合溶液中，并降温至0℃，加入87.8克(3.0当量)的叔丁醇钾(potassium tert-butoxide，KO-t-Bu)后在0℃下搅拌1小时，并接续在室温下搅拌12小时。在反应进行后，以去离子水急速冷却并以溶剂萃取获得有机层，再以硫酸钠达到除水的目的，接着透过减压蒸馏法去除有机层中的溶剂，并以硅胶柱层析纯化获得纯化产物，纯化产物经浓缩和干燥后可获得46.8克的淡黄色固体产物，产率为51.1％。
经FD-MS分析确定，淡黄色固体产物即为中间物A1-2。FD-MS分析结果：C19H11BrO2，理论值351.19，检测值为351.19。
步骤3：合成中间物A1-3
将53.5克(1.0当量)的中间物A1-2悬浮液和8.1克(0.025当量)5％的钯碳催化剂(palladium on carbon，Pd/C)在535毫升的乙酸乙酯(ethyl acetate，EA)中混合，并在氢气气球提供的氢气环境下搅拌3至6小时；接着，反应后的混合产物以硅藻土层过滤并以EA洗净，并使滤液在减压环境下进行浓缩，最后获得100克的黄色固体产物，产率为100％。
经FD-MS分析确定，黄色固体产物即为中间物A1-3。FD-MS分析结果：C19H13BrO2，理论值为353.21，检测值为353.21，中间物A1-3不需进一步纯化即可直接使用于接下来的步骤。
步骤4：合成中间物A1-4
53克(1.0当量)的中间物A1-3和57克(2.0当量)的对甲苯磺酸(p-toluenesulfonic acid，PTSA)在530毫升的甲苯中加热回流12小时，形成反应混合液；待反应混合液降至室温后，以碳酸氢钠饱和水溶液急速冷却反应混合液，再以二氯甲烷萃取获得有机层，并水洗有机层、使有机层浸泡在无水硫酸钠中干燥获得产物溶液，产物溶液减压浓缩，并以二氯甲烷和己烷体积比为1：1的洗脱液在硅胶柱中层析纯化，最后获得淡黄色固体产物，产率为91.5％。
经FD-MS分析确定，淡黄色固体产物即为中间物A1-4。FD-MS分析结果：C19H11BrO，理论值335.19，检测值为335.19。
中间物A2的合成
中间物A2用于制备一种新型化合物，中间物A2是以类似于合成中间物A1的步骤1至步骤4所合成，其差异在于起始物3-溴二苯并[a,d]环庚烯-5-酮用2-溴二苯并[a,d]环庚烯-5-酮(CAS No.198707-82-3)代替，中间物A2的合成路径示于合成机制A2中，在合成机制A2中所有中间物的分析方法均同前述，分析结果列于下表1。
Figure GDA0002397318850000321
中间物A3的合成
中间物A3用于制备一种新型化合物，中间物A3是以类似于合成中间物A1的步骤1至步骤4所合成，其差异在于起始物3-溴二苯并[a,d]环庚烯-5-酮用3,7-二溴二苯并[a,d]环庚烯-5-酮(3,7-dibromodibenzo[a,d]cyclohepten-5-one)(CAS No.226946-20-9)代替，中间物A3的合成路径示于合成机制A3中，在合成机制A3中所有中间物的分析方法均同前述，分析结果列于下表1。
Figure GDA0002397318850000331
表1：各中间物的化学结构式、产率、分子式与以FD-MS分析所得质量。
Figure GDA0002397318850000332
Figure GDA0002397318850000341
中间物A1至A3的修饰
除了中间物A1至A3之外，本领域技术人员可改变合成机制A1至A3中的起始物，并以类似于合成机制A1至A3的合成路径合成出其他中间物，例如以下列出的中间物A4至A15：
Figure GDA0002397318850000342
中间物B1的合成
前述中间物A1进一步与2-溴联苯(2-bromo-biphenyl)反应，以合成出中间物B1，该中间物B1的合成路径如合成机制B1所示。
Figure GDA0002397318850000351
步骤1：合成中间物B1-1
1.0当量的2-溴联苯溶解于120毫升的无水THF，并降温至-78℃，再将2.5M(1.0当量)的正丁基锂(n-butyl lithium，n-BuLi)缓慢加入前述低温溶液中并搅拌1小时后形成反应溶液。接着，将0.7当量的中间物A1加入反应溶液中在室温下搅拌3小时，反应完成后，以饱和氯化铵水溶液冷却，再以有机溶剂萃取出有机层，并将有机层分离、浓缩并以石油醚(petroleum ether)使之再结晶，最后可得白色固体产物，产率为83.1％。
经FD-MS分析确定，白色固体产物即为中间物B1-1。FD-MS分析结果：C31H21BrO，理论值489.40，检测值为489.40。
步骤2：合成中间物B1
将1.0当量的中间物B1-1、体积为中间物B1-1质量3倍的醋酸(即w/v＝1/3)和5滴的硫酸于110℃下搅拌混合6小时。然后减压蒸发去除溶剂，并以柱层析纯化残留物，接着以甲苯依序进行浓缩和再结晶的步骤，最后可得白色固体产物，产率为93.0％。
经FD-MS分析确定，白色固体产物即为中间物B1。FD-MS分析结果：C31H19Br，理论值471.39，检测值为471.39。
中间物B2的合成
中间物B2是以类似于合成中间物B1的步骤1和步骤2所合成，其差异在于将步骤1中的中间物A1用中间物A2代替，中间物B2的合成路径示于合成机制B2中。本实验是以如前述相同的分析方法分析合成机制B2中所得的所有中间物，分析结果列于下表2。
Figure GDA0002397318850000361
中间物B3的合成
中间物B3是以类似于合成中间物B1的步骤1和步骤2所合成，其差异在于将步骤1中的中间物A1用中间物A3代替，中间物B3的合成路径示于合成机制B3中。本实验是以如前述相同的分析方法分析合成机制B3中所得的所有中间物的，分析结果列于下表2。
Figure GDA0002397318850000362
表2：各中间物的化学结构式、产率、分子式与以FD-MS分析所得质量。
Figure GDA0002397318850000363
Figure GDA0002397318850000371
中间物B1至B3的修饰
除了中间物B1至B3之外，本领域技术人员可自中间物A1至A15中选择，以代替合成机制B1至B3中的起始物，并以类似于合成机制B1至B3的合成路径合成出其他中间物，例如下述的中间物B4至B15：
Figure GDA0002397318850000372
Figure GDA0002397318850000381
中间物C1的合成
前述中间物B1可进一步与联硼酸频那醇酯[bis(pinacolato)diboron]反应合成中间物C1，中间物C1可通过下述合成机制C1合成。
Figure GDA0002397318850000382
混合1.0当量的中间物B1、1.2当量的联硼酸频那醇酯、0.0025当量的[1,1-双(二苯基膦基)二茂铁]二氯化钯[1,1-bis(diphenylphosphino)-ferrocenedichloropalladium(II)，PdCl2(dppf)2]和3.0当量的醋酸钾在0.3M的1,4-二恶烷(1,4-dioxane)中，加热至100℃的并在氮气环境下搅拌8小时，冷却于室温后减压去除溶剂，并以柱层析仪纯化残留液而可获得白色固体产物，产率95.7％。
经由FD-MS分析确定，白色固体产物即为中间物C1。FD-MS分析结果：C37H31BO2，理论值518.45，检测值为518.45。
中间物C2的合成
中间物C2是以类似于中间物C1的方式所合成，其差异在于：该中间物B1是用中间物B2代替，中间物C2可通过下述合成机制C2合成，产率为96.1％。
经由FD-MS分析确定，获得的固体产物即为中间物C2。FD-MS分析结果：C37H31BO2，理论值518.45，检测值为518.45。
Figure GDA0002397318850000391
中间物C3的合成
中间物C3是以类似于中间物C1的方式所合成，其差异在于：该中间物B1是用中间物B3代替，且联硼酸频那醇酯的使用当量增加为2.4当量。具体而言，中间物C3可通过下述合成机制C3合成，产率为84.2％。
经由FD-MS分析确定，获得的固体产物即为中间物C3。FD-MS分析结果：C43H42B2O4，理论值644.41，检测值为644.40。
Figure GDA0002397318850000392
新型化合物I至XIV的合成
方法1：
中间物B1至B3均可被用于合成新型化合物，合成路径示于合成机制I中，其中，“中间物B”选自包括中间物B1至B3的群组，“反应物A(Reactant A)”选自下表3中包括反应物A1至A6的群组。
Figure GDA0002397318850000393
表3：各反应物A1至A6的化学结构式与CAS编号。
Figure GDA0002397318850000401
方法2：
中间物C1至C3可分别与各反应物合成出各种本发明所保护的新型化合物，该新型化合物可通过下述合成机制II所合成。其中，“中间物C”可以选自由中间物C1至C3所构成的群组；“反应物B”可以选自由表3-2中反应物B1至B5所构成的群组。
Figure GDA0002397318850000402
表3-2：各反应物B1至B5的的化学结构式与CAS编号。
Figure GDA0002397318850000403
具体而言，将1.2当量的反应物A、1.0当量的中间物B或C、0.005当量的三(二亚苄基丙酮)二钯[tris(dibenzylideneacetone)dipalladium(0)，Pd2(dba)3]、0.5％当量的乙酸钯[palladium acetate，Pd(OAc)2]、0.02当量的(SPhos)、0.5M甲苯和乙醇体积比为10：1的溶液中和3.0M的碳酸钾水溶液置于500毫升的茄形瓶中，在100℃通有氮气的环境下搅拌12小时；在此步骤中，可通过改变反应物A或反应物B以及催化剂的使用当量数，根据位置选择性(regioselectivity)合成出单一或偶联的产物。反应完成后，在茄形瓶中加入水和甲苯使反应溶液分层，接着，将萃取出的有机层以硫酸钠干燥，并减压蒸馏去除有机层中的溶剂，再将残留物以硅胶柱层析纯化，并以甲苯进行浓缩和再结晶的步骤，最后可得白色固体产物，即为本发明的新型化合物。
前述各种反应物和中间物可用于合成化合物I至化合物XIV并列于表4，化合物I至化合物XIV可通过氢核磁共振(1H nuclear magnetic resonance，1H-NMR)和FD-MS分析确定，并且，化合物I至化合物XIV的化学结构式、产率、分子式和以FD-MS分析所得质量也列于表4中。根据图2至图15以及表4的质量信息，化合物I至化合物XIV的化学结构式确认如下。
表4：合成各化合物I至化合物XIV使用的反应物、中间物、产率、分子式与以FD-MS分析所得质量。
Figure GDA0002397318850000411
Figure GDA0002397318850000421
Figure GDA0002397318850000431
化合物I至化合物XIV的修饰
除了前述化合物I至化合物XIV之外，本领域技术人员可选用其他反应物和中间物B1至B3或中间物C1至C3，并以类似于合成机制I或II的合成路径合成出本发明所保护的各种新型化合物。
OLED装置的制备
将涂布有
Figure GDA0002397318850000432
厚ITO层的玻璃基板(以下简称为ITO基板)置于含有洗洁剂(厂牌：Fischer Co.)的蒸馏水(以Millipore Co.公司的滤器过滤二次而得的蒸馏水)中，并以超声波震荡30分钟；更换蒸馏水后再以超声波震荡10分钟以洗净ITO基板，并重复上述洗净步骤一次；洗净后，将前述玻璃基板以异丙醇、丙酮和甲醇以超声波震荡洗净，并使之干燥；接着，将玻璃基板置于电浆表面清洁机内，并以氧电浆清洁玻璃基板5分钟，再将清洁后的玻璃基板置于真空蒸镀机内。
之后，将真空蒸镀机的真空度维持在1x10-6 torr至3x10-7 torr，并于ITO基板上依序沉积各种有机材料和金属材料，并获得上述实施例和比较例的OLED装置。因此，该ITO基板上依序沉积有第一电洞注入层(HIL-1)、第二电洞注入层(HIL-2)、第一电洞传输层(HTL-1)、第二电洞传输层(HTL-2)、蓝/绿/红发光层(BEL/GEL/REL)、电子传输层(ETL)、电子注入层(EIL)和阴极(Cthd)。
在上述OLED装置的各层中，HAT是用于形成HIL-1和HID；HI-2是用于形成HIL-2；HT-1和HT-2是用于形成HTL-1和HTL-2；传统的ET和本发明的新型化合物是用于形成ETL；Liq是用于形成ETD和EIL；RH/GH/BH分别为形成REL/GEL/BEL的主要材料；RD/GD/BD-1/BD-2可作为REL/GEL/BEL的掺杂物。实施例的OLED装置和比较例的OLED装置的主要差异为：比较例的OLED装置中ETL是以BCP制成，实施例的OELD装置中ETL是以列于表4的新型化合物所制成。上述各化合物的详细化学结构式列于表5。
表5：使用在OLED装置中商业材料的化学结构式。
Figure GDA0002397318850000441
红光OLED装置的制备
红光OLED装置包括多个有机层，各有机层依序沉积于ITO基板上，各有机层的材料和厚度分别列于表6中。
表6：红光OLED装置中各有机层的涂布顺序、名称、材料和厚度。
Figure GDA0002397318850000451
绿光OLED装置的制备
绿光OLED装置包括多个有机层，这些有机层依序沉积于ITO基板上，各有机层的材料和厚度分别列于表7中。
表7：绿光OLED装置中各有机层的涂布顺序、名称、材料和厚度。
Figure GDA0002397318850000453
蓝光OLED装置的制备
蓝光OLED装置包括多个有机层，这些有机层依序沉积于ITO基板上，各有机层的材料和厚度分别列于表8中。
针对蓝光OLED装置，发光层掺杂物可以是表5中的BD-1或BD-2，实施例B-4至B-8以及比较例B-1的OLED装置中所选用的掺杂物是BD-1；实施例B-1至B-3以及比较例B-2的OLED装置中所选用的掺杂物是BD-2。
表8：蓝光OLED装置中各有机层的涂布顺序、名称、材料和厚度。
Figure GDA0002397318850000452
Figure GDA0002397318850000461
OLED装置的效能
为了评估OLED装置的效能，分别将红光、绿光和蓝光OLED装置连接于电源供应器(厂牌：Keithley；型号：2400)，并以PR650的亮度计检测，所测得的色度以为国际照明委员会(Commission Internationale de L’Eclairage 1931，CIE)制定的色度坐标[colorcoordinate(x,y)]表示，检测结果列于下表9中。其中，蓝光和红光的OLED装置是在1000尼特(1nit＝1cd/m2)的亮度下检测；绿光的OLED装置是在3000尼特的亮度下检测。
实施例R-1至R-4和比较例R中OLED装置的ETL材料、颜色、CIE、驱动电压和电流效率列于下表9中。实施例G-1至G-5以及比较例G中OLED装置的ETL材料、颜色、CIE、驱动电压和电流效率列于下表10中。实施例B-1至B-8以及比较例B-1和B-2中OLED装置的ETL材料、颜色、CIE、驱动电压和电流效率列于下表11中。
表9：实施例R-1至R-4和比较例R中OLED装置的ETL材料、颜色、CIE、驱动电压和电流效率。
Figure GDA0002397318850000462
表10：实施例G-1至G-5和比较例G中OLED装置的ETL材料、颜色、CIE、驱动电压和电流效率。
Figure GDA0002397318850000463
表11：实施例B-1至B-8和比较例B-1和B-2中OLED装置的ETL材料、颜色、CIE、驱动电压和电流效率。
Figure GDA0002397318850000464
Figure GDA0002397318850000471
根据实验结果可知，相较于市面上电子传输层材料(BCP)，选用本发明的新型化合物作为电子传输材料可降低红光、绿光或蓝光OLED装置的驱动电压并提升电流效率。实验结果证实本发明的新型化合物确实能适用添加在各色OLED装置中，并可达到降低驱动电压和提升电流效率的功效。
上述实施例仅为说明本发明的例示，并非在任何方面限制本发明所主张的权利范围，本领域技术人员能根据本发明的精神针对例如取代基的数量、位置或排列加以调整。本发明所主张的权利范围应以权利要求书所述为准，而非仅限于上述具体实施例。

Claims (11)

1.一种化合物，其如下式(I-I)、(I-II)、(I-IV)至(I-VIII)以及(I-XIV)所示：
Figure FDA0002397318840000011
G1选自由下列所构成的群组：
Figure FDA0002397318840000021
G3至G5各自为氢原子；
其中，R1和R2分别为苯基、吡啶基或氰苯基；
其中，j、k和l分别为4的整数。
2.一种化合物，其如下式(I-III)、(I-IX)至(I-XIII)以及(I-XV)所示：
Figure FDA0002397318840000022
G1、G2各自选自由下列所构成的群组：
Figure FDA0002397318840000023
Figure FDA0002397318840000031
G3至G5各自为氢原子；
其中，j、k和l分别为4的整数。
3.根据权利要求2所述的化合物，其中G1和G2相同。
4.一种化合物，其如下式(I-I)、(I-II)以及(I-XIV)所示：
Figure FDA0002397318840000032
G1选自由下列所构成的群组：
Figure FDA0002397318840000033
G3至G5各自为氢原子；
其中，R1为氢原子或苯基，R2至R4各自为氢原子；
其中，n为4，p为1，o为0至4的整数；
其中，j、k和l分别为4的整数。
5.一种化合物，其如下式(I-III)、(I-IX)至(I-XIII)以及(I-XV)所示：
Figure FDA0002397318840000034
Figure FDA0002397318840000041
G1、G2各自选自由下列所构成的群组：
Figure FDA0002397318840000042
G3至G5各自为氢原子；
其中，R1为氢原子或苯基，R2至R4各自为氢原子；
其中，n为4，p为1，o为0至4的整数；
其中，j、k和l分别为4的整数。
6.根据权利要求5所述的化合物，其中G1和G2相同。
7.一种化合物，其中该化合物选自由下列所构成的群组：
Figure FDA0002397318840000043
Figure FDA0002397318840000051
8.一种有机电子装置，其包括第一电极、第二电极和设置于该第一电极和该第二电极间的有机层，其中该有机层包括根据权利要求1至7中任一项所述的化合物。
9.根据权利要求8所述的有机电子装置，其中该有机电子装置为有机发光二极管。
10.根据权利要求9所述的有机电子装置，其中该有机发光二极管包括：
电洞注入层，其形成于该第一电极上；
电洞传输层，其形成于该电洞注入层上；
发光层，其形成于该电洞传输层上；
电子传输层，其形成于该发光层上，该有机层为该电子传输层；和
电子注入层，其形成于该电子传输层和该第二电极之间。
11.根据权利要求9所述的有机电子装置，其中该有机发光二极管包括：
电洞注入层，其形成于该第一电极上；
电洞传输层，其形成于该电洞注入层上；
发光层，其形成于该电洞传输层上；
电洞阻挡层，其形成于该发光层上，该有机层为该电洞阻挡层；
电子传输层，其形成于该电洞阻挡层上；和
电子注入层，其形成于该电子传输层和该第二电极之间。
CN201710061133.3A 2016-01-27 2017-01-25 化合物及其有机电子装置 Expired - Fee Related CN107011248B (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201662287724P 2016-01-27 2016-01-27
US62/287,724 2016-01-27

Publications (2)

Publication Number Publication Date
CN107011248A CN107011248A (zh) 2017-08-04
CN107011248B true CN107011248B (zh) 2020-06-09

Family

ID=59359552

Family Applications (5)

Application Number Title Priority Date Filing Date
CN201710061133.3A Expired - Fee Related CN107011248B (zh) 2016-01-27 2017-01-25 化合物及其有机电子装置
CN201710061447.3A Expired - Fee Related CN107011183B (zh) 2016-01-27 2017-01-26 新颖化合物及包含其的有机电子装置
CN201710057247.0A Active CN107011181B (zh) 2016-01-27 2017-01-26 新颖化合物及包含其的有机电子装置
CN201710061445.4A Expired - Fee Related CN107011182B (zh) 2016-01-27 2017-01-26 新颖化合物及包含其的有机电子装置
CN201710063301.2A Expired - Fee Related CN107011387B (zh) 2016-01-27 2017-02-03 化合物及其制成的电子元件

Family Applications After (4)

Application Number Title Priority Date Filing Date
CN201710061447.3A Expired - Fee Related CN107011183B (zh) 2016-01-27 2017-01-26 新颖化合物及包含其的有机电子装置
CN201710057247.0A Active CN107011181B (zh) 2016-01-27 2017-01-26 新颖化合物及包含其的有机电子装置
CN201710061445.4A Expired - Fee Related CN107011182B (zh) 2016-01-27 2017-01-26 新颖化合物及包含其的有机电子装置
CN201710063301.2A Expired - Fee Related CN107011387B (zh) 2016-01-27 2017-02-03 化合物及其制成的电子元件

Country Status (3)

Country Link
US (5) US10312459B2 (zh)
CN (5) CN107011248B (zh)
TW (5) TWI629257B (zh)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10693075B2 (en) * 2016-08-09 2020-06-23 Shanghai Nichem Fine Chemical Co., Ltd. Spiro compound and organic electronic device comprising the same
TWI658038B (zh) * 2016-12-07 2019-05-01 彩豐精技股份有限公司 化合物及其有機電子裝置
JP6475793B2 (ja) * 2017-08-01 2019-02-27 彩豐精技股▲分▼有限公司 化合物およびこれを用いた有機電子デバイス
KR102158472B1 (ko) 2017-09-26 2020-09-23 롬엔드하스전자재료코리아유한회사 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2019066258A1 (en) * 2017-09-26 2019-04-04 Rohm And Haas Electronic Materials Korea Ltd. ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENCE DEVICE COMPRISING SAME
EP3502107B1 (en) * 2017-12-20 2022-01-26 Samsung Display Co., Ltd. 1-aminodibenzofuran-based compound and organic light-emitting device including the same
KR102202058B1 (ko) * 2018-03-30 2021-01-11 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
US20190372015A1 (en) * 2018-06-05 2019-12-05 Shanghai Nichem Fine Chemical Co., Ltd. Compound and organic electronic device comprising the same
WO2020009448A1 (en) * 2018-07-03 2020-01-09 Rohm And Haas Electronic Materials Korea Ltd. A plurality of host materials and organic electroluminescent device comprising the same
US20200274070A1 (en) * 2019-02-27 2020-08-27 Shanghai Nichem Fine Chemical Co., Ltd. Compound and organic electronic device using the same
CN110437133B (zh) * 2019-07-18 2022-10-14 中国科学院上海微系统与信息技术研究所 一种长寿命室温磷光材料及其制备方法和应用
CN110724105B (zh) * 2019-09-27 2021-05-04 宁波卢米蓝新材料有限公司 一种三亚菲含氮七元环化合物及其制备方法和应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110041730A (ko) * 2009-10-16 2011-04-22 에스에프씨 주식회사 축합방향족화합물 및 이를 이용한 유기전계발광소자
CN103833507A (zh) * 2013-12-25 2014-06-04 石家庄诚志永华显示材料有限公司 一系列有机电致发光材料及其制备方法与应用
CN103946215A (zh) * 2011-11-17 2014-07-23 默克专利有限公司 螺二氢吖啶衍生物和其作为有机电致发光器件用材料的用途
WO2016087017A1 (de) * 2014-12-01 2016-06-09 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020121638A1 (en) * 2000-06-30 2002-09-05 Vladimir Grushin Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds
US6864628B2 (en) * 2000-08-28 2005-03-08 Semiconductor Energy Laboratory Co., Ltd. Light emitting device comprising light-emitting layer having triplet compound and light-emitting layer having singlet compound
JP3960765B2 (ja) * 2001-09-03 2007-08-15 三洋電機株式会社 発光素子用発光材料
KR100676965B1 (ko) * 2005-03-05 2007-02-02 주식회사 두산 신규 이리듐 착화합물 및 이를 이용한 유기 전계 발광 소자
DE102007031220B4 (de) * 2007-07-04 2022-04-28 Novaled Gmbh Chinoide Verbindungen und deren Verwendung in halbleitenden Matrixmaterialien, elektronischen und optoelektronischen Bauelementen
WO2009073245A1 (en) * 2007-12-06 2009-06-11 Universal Display Corporation Light-emitting organometallic complexes
JP2010024149A (ja) 2008-07-16 2010-02-04 Toyo Ink Mfg Co Ltd ７員環構造を有する化合物およびその用途
US8753756B2 (en) * 2009-06-30 2014-06-17 Chien-Hong Cheng Green phosphorescent iridium complexes, fabrication method thereof and organic light-emitting diodes comprising the same
JP4474493B1 (ja) * 2009-07-31 2010-06-02 富士フイルム株式会社 有機電界発光素子
TW201223956A (en) * 2010-08-13 2012-06-16 Solvay Light emitting materials for electronics
KR20120047038A (ko) 2010-11-03 2012-05-11 에스에프씨 주식회사 아민 유도체 및 이를 포함하는 유기전계발광소자
KR101421521B1 (ko) 2010-11-05 2014-07-24 에스에프씨 주식회사 아민 유도체 화합물 및 이를 포함하는 유기전계발광소자
KR101996651B1 (ko) 2011-02-14 2019-07-04 에스에프씨 주식회사 플루오렌 유도체 및 이를 포함하는 유기전계발광소자
KR102013400B1 (ko) * 2012-03-29 2019-08-22 에스에프씨 주식회사 인데노페난트렌 유도체 및 이를 포함하는 유기전계발광소자
KR20130140303A (ko) 2012-06-14 2013-12-24 (주) 에프엔지리서치 유기전계발광 소자 제조용 신규 화합물
CN103936720B (zh) * 2013-12-12 2016-03-02 石家庄诚志永华显示材料有限公司 含有螺芴结构单元的化合物及其制备方法与应用
TWI534141B (zh) 2014-10-15 2016-05-21 彩豐精技股份有限公司 以順式二苯乙烯／芴螺旋體衍生的雙極型化合物
TWI558688B (zh) 2014-10-15 2016-11-21 彩豐精技股份有限公司 順式二苯乙烯／芴螺旋體衍生的光電材料
EP3254317B1 (de) * 2015-02-03 2019-07-31 Merck Patent GmbH Metallkomplexe
US10169105B2 (en) * 2015-07-30 2019-01-01 Qualcomm Incorporated Method for simplified task-based runtime for efficient parallel computing
CN106432078B (zh) 2015-08-04 2019-05-24 彩丰精技股份有限公司 化合物及使用其的有机电子装置
KR102573815B1 (ko) 2016-05-09 2023-09-04 삼성디스플레이 주식회사 다환 화합물 및 이를 포함하는 유기 전계 발광 소자
CN106467469A (zh) 2016-06-13 2017-03-01 江苏三月光电科技有限公司 一种有机电致发光化合物及其应用

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20110041730A (ko) * 2009-10-16 2011-04-22 에스에프씨 주식회사 축합방향족화합물 및 이를 이용한 유기전계발광소자
CN103946215A (zh) * 2011-11-17 2014-07-23 默克专利有限公司 螺二氢吖啶衍生物和其作为有机电致发光器件用材料的用途
CN103833507A (zh) * 2013-12-25 2014-06-04 石家庄诚志永华显示材料有限公司 一系列有机电致发光材料及其制备方法与应用
WO2016087017A1 (de) * 2014-12-01 2016-06-09 Merck Patent Gmbh Materialien für organische elektrolumineszenzvorrichtungen

Also Published As

Publication number Publication date
CN107011182B (zh) 2020-08-07
US20170213971A1 (en) 2017-07-27
TW201726609A (zh) 2017-08-01
CN107011248A (zh) 2017-08-04
CN107011183A (zh) 2017-08-04
CN107011387A (zh) 2017-08-04
TWI653215B (zh) 2019-03-11
CN107011181A (zh) 2017-08-04
CN107011183B (zh) 2019-05-24
US20170213970A1 (en) 2017-07-27
US10424744B2 (en) 2019-09-24
US20170213972A1 (en) 2017-07-27
CN107011182A (zh) 2017-08-04
TWI656110B (zh) 2019-04-11
TWI629257B (zh) 2018-07-11
TW201726699A (zh) 2017-08-01
TWI632148B (zh) 2018-08-11
TW201726603A (zh) 2017-08-01
TWI635068B (zh) 2018-09-11
CN107011387B (zh) 2019-11-19
TW201726604A (zh) 2017-08-01
US20170213990A1 (en) 2017-07-27
US10326087B2 (en) 2019-06-18
CN107011181B (zh) 2020-09-15
US10431751B2 (en) 2019-10-01
US20170213978A1 (en) 2017-07-27
US10312459B2 (en) 2019-06-04
TW201726601A (zh) 2017-08-01

Similar Documents

Publication Publication Date Title
CN107011248B (zh) 化合物及其有机电子装置
CN107382926B (zh) 化合物及其有机电子装置
TWI641598B (zh) 化合物及其有機電子裝置
JP6539823B2 (ja) 化合物およびこれを用いた有機電子デバイス
KR102243851B1 (ko) 화합물 및 이를 포함하는 유기 전자 소자
CN108164496B (zh) 化合物及其有机电子装置
CN107698570B (zh) 化合物及其有机电子装置
JP6539821B2 (ja) 化合物およびこれを用いた有機電子デバイス
TWI644912B (zh) 化合物和使用其的有機電子裝置
KR101915648B1 (ko) 화합물 및 이를 이용한 유기 전자 장치

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

Effective date of registration: 20190515

Address after: 888 C Building, Huanhu West Second Road, Nanhui New Town, Pudong New District, Shanghai

Applicant after: SHANGHAI NICHEM FINE CHEMICAL Co.,Ltd.

Address before: Hsinchu County, Taiwan, China

Applicant before: NICHEM FINE TECHNOLOGY Co.,Ltd.

TA01 Transfer of patent application right
GR01 Patent grant
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20200609

CF01 Termination of patent right due to non-payment of annual fee