US20180002256A1 - Double-spiro type compound and organic light-emitting device containing same - Google Patents

Double-spiro type compound and organic light-emitting device containing same Download PDF

Info

Publication number
US20180002256A1
US20180002256A1 US15/545,577 US201615545577A US2018002256A1 US 20180002256 A1 US20180002256 A1 US 20180002256A1 US 201615545577 A US201615545577 A US 201615545577A US 2018002256 A1 US2018002256 A1 US 2018002256A1
Authority
US
United States
Prior art keywords
direct bond
group
substituted
unsubstituted
chemical formula
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.)
Abandoned
Application number
US15/545,577
Other languages
English (en)
Inventor
Yongbum CHA
Jin Joo Kim
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.)
LG Chem Ltd
Original Assignee
LG Chem 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 LG Chem Ltd filed Critical LG Chem Ltd
Assigned to LG CHEM, LTD. reassignment LG CHEM, LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHA, Yongbum, KIM, JIN JOO
Publication of US20180002256A1 publication Critical patent/US20180002256A1/en
Abandoned legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/72—Spiro hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—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
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • 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
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/18—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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D263/57—Aryl or substituted aryl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • 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
    • H01L51/50—
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • 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
    • H10K85/654—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
    • C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
    • 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
    • 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
    • C07C2603/96—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members
    • C07C2603/97—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members containing five-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
    • C09K2211/1011—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
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • 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
    • H10K85/649—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

Definitions

  • the present specification relates to a double spiro structure compound and an organic light emitting device comprising the same.
  • An organic light emission phenomenon generally refers to a phenomenon converting electrical energy to light energy using an organic material.
  • An organic light emitting device using an organic light emission phenomenon normally has a structure comprising an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often formed in a multilayer structure formed with different materials in order to increase efficiency and stability of the organic light emitting device, and for example, may be formed with a hole injection layer, a hole transfer layer, a light emitting layer, an electron transfer layer, an electron injection layer and the like.
  • the present specification provides a double spiro structure compound and an organic light emitting device comprising the same.
  • One embodiment of the present specification provides a double spiro structure compound represented by the following Chemical Formula 1.
  • R 1 is represented by any one of the following Chemical Formula A to Chemical Formula C.
  • X 1 to X 3 are the same as or different from each other, and each independently CH or N,
  • At least one of X 1 to X 3 is N,
  • X 4 is O, S or NAr 5 ,
  • L 1 to L 3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms,
  • Ar 1 to Ar 5 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and
  • Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or multicyclic heteroring having 2 to 30 carbon atoms.
  • Another embodiment of the present invention provides an organic light emitting device comprising an anode; a cathode provided opposite to the anode; and a light emitting layer and one or more organic material layers provided between the anode and the cathode, wherein the light emitting layer and one or more layers of the organic material layers comprise the double spiro structure compound represented by Chemical Formula 1.
  • Compounds according to one embodiment of the present invention can be used as a material of an organic material layer of an organic light emitting device, and by using the compounds, efficiency enhancement, a low driving voltage and/or lifespan property enhancement can be accomplished in the organic light emitting device.
  • FIG. 1 is a diagram showing an organic light emitting device ( 10 ) according to one embodiment of the present specification.
  • FIG. 2 is a diagram showing an organic light emitting device ( 11 ) according to another embodiment of the present specification.
  • the present specification provides a double spiro structure compound represented by Chemical Formula 1.
  • a description of one member being placed “on” another member includes not only a case of the one member adjoining the another member but a case of still another member being present between the two members.
  • an “adjacent” group may mean a substituent substituting an atom directly linking to an atom substituted by the corresponding substituent, a substituent sterically most closely positioned to the corresponding substituent, or another substituent substituting an atom substituted by the corresponding substituent.
  • two substituents substituting ortho positions in a benzene ring, and two substituents substituting the same carbon in an aliphatic ring may be interpreted as “adjacent” groups.
  • substitution means a hydrogen atom bonding to a carbon atom of a compound is changed to another substituent, and the position of substitution is not limited as long as it is a position at which the hydrogen atom is substituted, that is, a position at which a substituent can substitute, and when two or more substituents substitute, the two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted in the present specification means being substituted with one, two or more substituents selected from the group consisting of deuterium; a halogen group; a nitrile group; a nitro group; an imide group; an amide group; a carbonyl group; an ester group; a hydroxyl group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted alkylthioxy group; a substituted or unsubstituted arylthioxy group; a substituted or unsubstituted alkylsulfoxy group; a substituted or unsubstituted arylsulfoxy group; a substituted or unsubstituted alkenyl group;
  • the halogen group may include fluorine, chlorine, bromine or iodine.
  • the number of carbon atoms of the imide group is not particularly limited, but is preferably from 1 to 30. Specifically, compounds having structures such as below may be included, but the imide group is not limited thereto.
  • the nitrogen of the amide group may be substituted with a linear, branched or cyclic alkyl group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • compounds having the following structural formulae may be included, but the amide group is not limited thereto.
  • the number of carbon atoms of the carbonyl group is not particularly limited, but is preferably from 1 to 30. Specifically, compounds having structures such as below may be included, but the carbonyl group is not limited thereto.
  • the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms may be included, but the ester group is not limited thereto.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably from 1 to 30. Specific examples thereof may include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specific examples thereof may include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl and the like, but are not limited thereto.
  • the alkoxy group may be linear, branched or cyclic.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably from 1 to 30. Specific examples thereof may include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benxyloxy, p-methylbenxyloxy and the like, but are not limited thereto.
  • the amine group may be selected from the group consisting of —NH 2 ; an alkylamine group; an N-alkylarylamine group; an arylamine group; an N-arylheteroarylamine group; an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is, although not particularly limited thereto, preferably 1 to 30.
  • the amine group may include a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, an N-9-methyl-anthracenylamine group, a diphenylamine group, an N-phenylnaphthylamine group, a ditolylamine group, an N-phenyltolylamine group, a triphenylamine group, an N-biphenylfluorenylamine group, an N-phenylfluorenylamine group, an N-phenylspirobifluorenylamine group, an N-biphenylspirobifluorenylamine group, an N-biphenyldibenzofuranylamine group, an N-phenylphenanthrenylamine group, an N-biphenyl
  • the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.
  • the N-arylheteroarylamine group means an amine group in which N of the amine group is substituted with an aryl group and a heteroaryl group.
  • the N-alkylheteroarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and a heteroarylamine group.
  • the alkyl group in the alkylamine group, the N-alkylarylamine group, the N-alkylheteroarylamine group, the alkylthioxy group and the alkylsulfoxy group is the same as the examples of the alkyl group described above.
  • the alkylthioxy group may include a methylthioxy group, an ethylthioxy group, a tert-butylthioxy group, a hexylthioxy group, an octylthioxy group and the like
  • the alkylsulfoxy group may include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, a butylsulfoxy group and the like, however, the examples are not limited thereto.
  • the alkenyl group may be linear or branched, and although not particularly limited thereto, the number of carbon atoms is preferably from 2 to 30. Specific examples thereof may include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, a stilbenyl group, a styrenyl group and the like, but are not limited thereto.
  • silyl group may include a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group and the like, but are not limited thereto.
  • the boron group may be —BR 100 R 101 R 102 , and herein, R 100 , R 101 and R 102 are the same as or different from each other, and may be each independently selected from the group consisting of hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted monocyclic or multicyclic cycloalkyl group having 3 to 30 carbon atoms; a substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or multicyclic heteroaryl group having 2 to 30 carbon atoms.
  • phosphine oxide group may include a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, a dimethylphosphine oxide group and the like, but are not limited thereto.
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but is preferably from 6 to 30.
  • Specific examples of the monocyclic aryl group may include a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group and the like, but are not limited thereto.
  • the number of carbon atoms is not particularly limited, but is preferably from 10 to 30.
  • Specific examples of the multicyclic aryl group may include a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenyl group, a crycenyl group, a fluorenyl group, a fluoranthenyl group and the like, but are not limited thereto.
  • the fluorenyl group may be substituted, and adjacent substituents may bond to each to form a ring.
  • the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-alkylarylamine group, the N-arylheteroarylamine group and the arylphosphine group may be same as the examples of the aryl group described above.
  • aryloxy group may include phenoxy, p-tolyloxy, m-tolyloxy, 3,5-dimethyl-phenoxy, 2,4,6-trimethylphenoxy, p-tert-butylphenoxy, 3-biphenyloxy, 4-biphenyloxy, 1-naphthyloxy, 2-naphthyloxy, 4-methyl-1-naphthyloxy, 5-methyl-2-naphthyloxy, 1-anthryloxy, 2-anthryloxy, 9-anthryloxy, 1-phenanthryloxy, 3-phenanthryloxy, 9-phenanthryloxy and the like
  • specific examples of the arylthioxy group may include a phenylthioxy group, a 2-methylphenylthioxy group, a 4-tert-butylphenylthioxy group and the like
  • specific examples of the arylsulfoxy group may include a benzenesulfoxy group, a p-tolu
  • examples of the arylamine group may include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group or a multicyclic aryl group.
  • the arylamine group comprising two or more aryl groups may include monocyclic aryl groups, multicyclic aryl groups, or both a monocyclic aryl group and a multicyclic aryl group.
  • the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
  • the heteroaryl group is a group comprising one or more atoms that are not carbon, that is, heteroatoms, and specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, Se, S and the like.
  • the number of carbon atoms is not particularly limited, but is favorably from 2 to 30, and the heteroaryl group may be monocyclic or multicyclic.
  • heteroaryl group may include a thiophene group, a furanyl group, a pyrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, triazinyl group, a triazolyl group, an acridyl group, a pyridazinyl group, a pyrazinyl group, a qinolinyl group, a quinazolinyl group, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolinyl group, an indolyl group,
  • examples of the heteroarylamine group may include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group.
  • the heteroarylamine group comprising two or more heteroaryl groups may include monocyclic heteroaryl groups, multicyclic heteroaryl groups, or both a monocyclic heteroaryl group and a multicyclic heteroaryl group.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroring group described above.
  • heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the heteroaryl group described above.
  • the heteroring group may be monocyclic or multicyclic, may be aromatic, aliphatic or a fused ring of aromatic and aliphatic, and may be selected from the examples of the heteroaryl group.
  • the arylene group means an aryl group having two bonding sites, that is, a divalent group. Descriptions on the aryl group made above may be applied except for those that are each a divalent group.
  • the heteroarylene group means a heteroaryl group having two bonding sites, that is, a divalent group. Descriptions on the heteroaryl group made above may be applied except for those that are each a divalent group.
  • the hydrocarbon ring may be aromatic, aliphatic or a fused ring of aromatic and aliphatic, and may be selected from the examples of the cycloalkyl group or the aryl group except for those are not monovalent.
  • the aromatic ring may be monocyclic or multicyclic, and may be selected from the examples of the aryl group except for those are not monovalent.
  • the heteroring is a group comprising one or more atoms that are not carbon, that is, heteroatoms, and specifically, the heteroatom may include one or more atoms selected from the group consisting of O, N, Se, S and the like.
  • the heteroring may be monocyclic or multicyclic, may be aromatic, aliphatic or a fused ring of aromatic and aliphatic, and may be selected from the examples of the heteroaryl group except for those are not monovalent.
  • the double spiro structure compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulae 2 to 4.
  • the double spiro structure compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulae 1-1 to 1-3.
  • the double spiro structure compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulae 2-1 to 2-3.
  • X 1 to X 3 are the same as or different from each other, and each independently CH or N, and at least one of X 1 to X 3 is N.
  • X 1 to X 3 are the same as or different from each other, and each independently CH or N, and at least two of X 1 to X 3 are N.
  • X 1 to X 3 are N.
  • the double spiro structure compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulae 3-1 to 3-4.
  • the double spiro structure compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulae 3-5 to 3-16.
  • Chemical Formula 1 may be represented by any one of the following Chemical Formula 4-1 to Chemical Formula 4-3.
  • Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 30 carbon atoms.
  • Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 20 carbon atoms.
  • Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 10 carbon atoms.
  • Cy1 is a substituted or unsubstituted benzene ring.
  • Cy1 is a benzene ring.
  • Chemical Formula 1 may be represented by the following Chemical Formula 4-4.
  • the double spiro structure compound represented by Chemical Formula 1 may be represented by any one of the following Chemical Formulae 4-5 to 4-7.
  • L 1 to L 3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 20 carbon atoms.
  • L 1 to L 3 are the same as or different from each other, and each independently a direct bond; or a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 15 carbon atoms.
  • L 1 to L 3 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylylene group.
  • L 1 to L 3 are the same as or different from each other, and each independently a direct bond; a phenylene group; or a biphenylylene group.
  • Ar 1 to Ar 5 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 25 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms.
  • a substituted or unsubstituted arylamine group a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 25 carbon atoms
  • a substituted or unsubstituted heteroaryl group having 2 to 25 carbon atoms.
  • Ar 1 to Ar 5 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted quaterphenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted terphenylenyl group; a substituted or unsubstituted dibenzothiophene group; and a substituted or unsubstituted dibenzofuran group.
  • Ar 1 to Ar 5 are the same as or different from each other, and each independently selected from the group consisting of a phenyl group; a biphenylyl group; a naphthyl group; a terphenyl group; a quaterphenyl group; a fluorenyl group; a phenanthrenyl group; a terphenylenyl group; a dibenzothiophene group; and a dibenzofuran group, and
  • Ar 1 to Ar 5 may be unsubstituted or substituted with one or more selected from the group consisting of deuterium; a fluorine group; a nitrile group; a methyl group; a phenyl group; a biphenyl group; a naphthyl group; a fluorenyl group; a phenanthrenyl group; a dibenzothiophene group; a dibenzofuran group; a carbazolyl group; a benzocarbazolyl group; a diphenylamine group; a dibiphenylamine group; an N-phenylbiphenylamine group; an N-phenylfluorenylamine group; and an N-biphenylfluorenylamine group.
  • Ar 1 to Ar 5 are the same as or different from each other, and may be each independently selected as any one among the following structural formulae.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted quaterphenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted terphenylenyl group; a substituted or unsubstituted dibenzothiophene group; and a substituted or unsubstituted dibenzofuran group.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently selected from the group consisting of a phenyl group; a biphenylyl group; a naphthyl group; a terphenyl group; a quaterphenyl group; a fluorenyl group; a phenanthrenyl group; a terphenylenyl group; a dibenzothiophene group; and a dibenzofuran group, and
  • Ar 1 and Ar 2 may be unsubstituted or substituted with one or more selected from the group consisting of deuterium; a fluorine group; a nitrile group; a methyl group; a phenyl group; a biphenyl group; a naphthyl group; a fluorenyl group; a dibenzothiophene group; a dibenzofuranyl group; a carbazolyl group; a benzocarbazolyl group; a diphenylamine group; a dibiphenylamine group; an N-phenylbiphenylamine group; an N-phenylfluorenylamine group; and an N-biphenylfluorenylamine group.
  • Ar 1 and Ar 2 are the same as or different from each other, and may be each independently selected as any one among the following structural formulae.
  • Ar 3 and Ar 4 are the same as or different from each other, and each independently selected from the group consisting of a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted fluorenyl group; and a substituted or unsubstituted phenanthrenyl group.
  • Ar 3 and Ar 4 are the same as or different from each other, and each independently selected from the group consisting of a phenyl group; a biphenylyl group; a naphthyl group; a terphenyl group; a fluorenyl group; and a phenanthrenyl group, and
  • Ar 3 and Ar 4 may be unsubstituted or substituted with one or more selected from the group consisting of a methyl group; a phenyl group; a biphenyl group; a naphthyl group; and a fluorenyl group.
  • Ar 3 and Ar 4 are the same as or different from each other, and may be each independently selected as any one among the following structural formulae.
  • Ar 5 is selected from the group consisting of a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenylyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted dibenzothiophene group; and a substituted or unsubstituted dibenzofuran group.
  • Ar 5 is selected from the group consisting of a phenyl group; a biphenylyl group; a naphthyl group; a terphenyl group; a fluorenyl group; a phenanthrenyl group; a dibenzothiophene group; and a dibenzofuran group, and
  • Ar 5 may be unsubstituted or substituted with one or more selected from the group consisting of a methyl group; a phenyl group; a biphenyl group; a naphthyl group; a phenanthrenyl group; and a fluorenyl group.
  • Ar 5 may be selected as any one among the following structural formulae.
  • the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 2, and in the following Chemical Formula 2, L 1 , Ar 1 and Ar 2 are any one selected from among 2-1-1 to 2-1-334 of the following Table 1.
  • the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 2-1 to 2-3, and in the following Chemical Formulae 2-1 to 2-3, L 1 , Ar 1 and Ar 2 may be selected from Table 1.
  • L 1 when Ar 1 and Ar 2 correspond to 2-1-10 in Table 1, it may be expressed as Compound 2-1-10 (2-1), and when corresponding to 2-1-20, it may be expressed as Compound 2-1-20 (2-1).
  • the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-1, and in the following Chemical Formula 3-1, L 2 , Ar 3 and Ar 4 are any one selected from among 3-1-1 to 3-1-104 of the following Table 2.
  • the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 3-5 to 3-7, and in the following Chemical Formulae 3-5 to 3-7, L 2 , Ar 3 and Ar 4 may be selected from Table 2.
  • L 2 , Ar 3 and Ar 4 may be selected from Table 2.
  • L 2 , Ar 3 and Ar 4 when L 2 , Ar 3 and Ar 4 correspond to 3-1-10 in Table 2, it may be expressed as Compound 3-1-10 (3-5), and when corresponding to 3-1-20, it may be expressed as Compound 3-1-20 (3-5).
  • the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-2, and in the following Chemical Formula 3-2, L 2 , Ar 3 and Ar 4 are any one selected from among 3-2-1 to 3-2-104 of the following Table 3.
  • the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 3-8 to 3-10, and in the following Chemical Formulae 3-8 to 3-10, L 2 , Ar 3 and Ar 4 may be selected from Table 3.
  • L 2 , Ar 3 and Ar 4 may be selected from Table 3.
  • t when L 2 , Ar 3 and Ar 4 correspond to 3-2-10 in Table 3, t may be expressed as Compound 3-2-10 (3-8), and when corresponding to 3-2-20, it may be expressed as Compound 3-2-20 (3-8).
  • the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-3, and in the following Chemical Formula 3-3, L 2 , Ar 3 and Ar 4 are any one selected from among 3-3-1 to 3-3-104 of the following Table 4.
  • the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 3-11 to 3-13, and in the following Chemical Formulae 3-11 to 3-13, L 2 , Ar 3 and Ar 4 may be selected from Table 4.
  • L 2 when Ar 3 and Ar 4 correspond to 3-3-10 in Table 4, it may be expressed as Compound 3-3-10 (3-11), and when corresponding to 3-3-20, it may be expressed as Compound 3-3-20 (3-11).
  • the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 3-4, and in the following Chemical Formula 3-4, L 2 , Ar 3 and Ar 4 are any one selected from among 3-4-1 to 3-4-104 of the following Table 5.
  • the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 3-14 to 3-16, and in the following Chemical Formulae 3-14 to 3-16, L 2 , Ar 3 and Ar 4 may be selected from Table 5.
  • L 2 , Ar 3 and Ar 4 when L 2 , Ar 3 and Ar 4 correspond to 3-4-10 in Table 5, it may be expressed as Compound 3-4-10 (3-14), and when corresponding to 3-4-20, it may be expressed as Compound 3-4-20 (3-14).
  • the double spiro structure compound represented by Chemical Formula 1 is represented by the following Chemical Formula 4-4, and in the following Chemical Formula 4-4, L 3 and X 4 are any one selected from among 4-4-1 to 4-4-22 of the following Table 6.
  • the double spiro structure compound represented by Chemical Formula 1 is represented by any one of the following Chemical Formulae 4-5 to 4-7, and in the following Chemical Formulae 4-5 to 4-7, L 3 and X 4 may be selected from Table 6.
  • L 3 and X 4 may be selected from Table 6.
  • L 3 and X 4 when L 3 and X 4 correspond to 4-4-10 in Table 6, it may be expressed as Compound 4-4-10 (4-5), and when corresponding to 4-4-20, it may be expressed as Compound 4-4-20 (4-5).
  • One embodiment of the present specification provides an organic light emitting device comprising an anode; a cathode provided opposite to the anode; and a light emitting layer and one or more organic material layers provided between the anode and the cathode, wherein the light emitting layer or one or more layers of the organic material layers comprise the double spiro structure compound represented by Chemical Formula 1.
  • the organic material layer of the organic light emitting device of the present specification may be formed in a single layer structure, but may be formed in a multilayer structure in which two or more organic material layers are laminated.
  • the organic light emitting device of the present invention may have a structure comprising a hole injection layer, a hole transfer layer, an electron blocking layer, a hole blocking layer, an electron transfer layer, an electron injection layer and the like as the organic material layer.
  • the structure of the organic light emitting device is not limited thereto, and may comprise less numbers of organic material layers.
  • the structure of the organic light emitting device of the present invention may be as shown in FIG. 1 and FIG. 2 , but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device ( 10 ) in which an anode ( 30 ), a light emitting layer ( 40 ) and a cathode ( 50 ) are consecutively laminated on a substrate ( 20 ).
  • FIG. 1 is an illustrative structure of the organic light emitting device according to one embodiment of the present specification, and other organic material layers may be further included therein.
  • FIG. 2 illustrates a structure of an organic light emitting device in which an anode ( 30 ), a hole injection layer ( 60 ), a hole transfer layer ( 70 ), a light emitting layer ( 40 ), an electron transfer layer ( 80 ), an electron injection layer ( 90 ) and a cathode ( 50 ) are consecutively laminated on a substrate ( 20 ).
  • FIG. 2 is an illustrative structure of the organic light emitting device according to one embodiment of the present specification, and other organic material layers may be further included therein.
  • the organic material layer comprises a hole injection layer or a hole transfer layer
  • the hole injection layer or the hole transfer layer comprises the double spiro structure compound represented by Chemical Formula 1.
  • the organic material layer comprises an electron blocking layer
  • the electron blocking layer comprises the double spiro structure compound represented by Chemical Formula 1.
  • the light emitting layer comprises the double spiro structure compound represented by Chemical Formula 1.
  • the organic material layer comprises an electron transfer layer or an electron injection layer, wherein the electron transfer layer or the electron injection layer comprises the double spiro structure compound represented by Chemical Formula 1.
  • the organic material layer comprises an electron transfer layer, an electron injection layer, or a layer carrying out electron transfer and electron injection at the same time
  • the electron transfer layer, the electron injection layer, or the layer carrying out electron transfer and electron injection at the same time comprises the double spiro structure compound represented by Chemical Formula 1.
  • the organic light emitting device comprises one or more organic material layers provided between the anode and the light emitting layer, wherein the organic material layer comprises a double spiro structure compound represented by the following Chemical Formula 2.
  • L 1 is a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms, and
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • the double spiro structure compound represented by Chemical Formula 2 may be represented by any one of Chemical Formulae 2-1 to 2-3 described above.
  • the organic light emitting device comprises one or more organic material layers provided between the cathode and the light emitting layer, and the light emitting layer and one or more layers of the organic material layers comprise a double spiro structure compound represented by the following Chemical Formula 3.
  • X 1 to X 3 are the same as or different from each other, and each independently CH or N,
  • At least one of X 1 to X 3 is N,
  • L 2 is a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or multicyclic heteroarylene group having 2 to 30 carbon atoms, and
  • Ar 3 and Ar 4 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • the double spiro structure compound represented by Chemical Formula 3 may be represented by any one of Chemical Formulae 3-1 to 3-9 described above.
  • the organic light emitting device comprises one or more organic material layers provided between the cathode and the light emitting layer, wherein the organic material layer comprises a double spiro structure compound represented by the following Chemical Formula 4.
  • X 4 is O, S or NAr 5 ,
  • L 3 is a direct bond; a substituted or unsubstituted monocyclic or multicyclic arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or multicyclic heteroarylene group having 2 to 30 carbon atoms,
  • Ar 5 is selected from the group consisting of hydrogen; a substituted or unsubstituted arylamine group; a substituted or unsubstituted monocyclic or multicyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms, and
  • Cy1 is a substituted or unsubstituted monocyclic or multicyclic hydrocarbon ring having 3 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or multicyclic heteroring having 2 to 30 carbon atoms.
  • the double spiro structure compound represented by Chemical Formula 4 may be represented by any one of Chemical Formulae 4-1 to 4-3 described above.
  • the organic light emitting device of the present specification may be manufactured using materials and methods known in the art, except that one or more layers of organic material layers comprise the double spiro structure compound of the present specification, that is, the double spiro structure compound represented by Chemical Formula 1.
  • the organic material layers may be formed with the same material or with different materials.
  • the organic light emitting device of the present specification may be manufactured by consecutively laminating an anode, an organic material layer and a cathode on a substrate.
  • the organic light emitting device may be manufactured by forming the anode on the substrate by depositing a metal, a metal oxide having conductivity, or alloys thereof using a physical vapor deposition (PVD) method such as a sputtering method or an e-beam evaporation method, forming the organic material layer comprising a hole injection layer, a hole transfer layer, a light emitting layer and an electron transfer layer thereon, then depositing a material capable of being used as the cathode thereon.
  • PVD physical vapor deposition
  • the organic light emitting device may be manufactured by consecutively depositing a cathode material, an organic material layer, and an anode material.
  • the double Spiro structure compound represented by Chemical Formula 1 may be formed as the organic material layer using a solution coating method as well as a vacuum deposition method.
  • the solution coating method means spin coating, dip coating, doctor blading, ink jet printing, screen printing, a spray method, roll coating and the like, but is not limited thereto.
  • anode material a material having large work function is normally preferable so that hole injection to the organic material layer is smooth.
  • the anode material capable of being used in the present invention include metals such as vanadium, chromium, copper, zinc and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO) and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylen-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material a material having small work function is normally preferable so that electron injection to the organic material layer is smooth.
  • the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF/Al, LiO 2 /Al or Mg/Ag, and the like, but are not limited thereto.
  • the hole injection layer is a layer that injects holes from an electrode
  • the hole injection material is preferably a compound that has an ability to transfer holes, therefore, has a hole injection effect in an anode, has an excellent hole injection effect for a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from moving to an electron injection layer or an electron injection material, and in addition, has an excellent thin film forming ability.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is preferably in between the work function of an anode material and the HOMO of surrounding organic material layers.
  • the hole injection material examples include a metal porphyrin, oligothiophene, an arylamine-based organic material, a hexanitrile hexazatriphenylene-based organic material, a quinacridone-based organic material, a perylene-based organic material, anthraquinone, and a polyaniline- and a polythiophene-based conductive polymer, and the like, but are not limited thereto.
  • the hole transfer layer is a layer that receives holes from a hole injection layer and transfers the holes to a light emitting layer
  • a hole transfer material a material capable of receiving holes from an anode or a hole injection layer, moving the holes to a light emitting layer, and having high mobility for the holes, is suitable.
  • Specific examples thereof include an arylamine-based organic material, a conductive polymer, a block copolymer having conjugated parts and non-conjugated parts together, and the like, but are not limited thereto.
  • a light emitting material of the light emitting layer is a material capable of emitting light in a visible light region by receiving holes and electrons from a hole transfer layer and an electron transfer layer, respectively, and binding the holes and the electrons, and is preferably a material having favorable quantum efficiency for fluorescence or phosphorescence.
  • Specific examples thereof include a 8-hydroxy-quinoline aluminum complex (Alq 3 ); a carbazole-based compound; a dimerized styryl compound; BAlq; a 10-hydroxybenzo quinoline-metal compound; a benzoxazole-, a benzthiazole- and a benzimidazole-based compound; a poly(p-phenylenevinylene) (PPV)-based polymer; a spiro compound; polyfluorene, rubrene, and the like, but are not limited thereto.
  • Alq 3 8-hydroxy-quinoline aluminum complex
  • a carbazole-based compound a dimerized styryl compound
  • BAlq a 10-hydroxybenzo quinoline-metal compound
  • a benzoxazole-, a benzthiazole- and a benzimidazole-based compound a poly(p-phenylenevinylene) (PPV)-based polymer
  • PPV poly(p-
  • the light emitting layer may comprise a host material and a dopant material.
  • the host material includes a fused aromatic ring derivative, a heteroring-containing compound or the like.
  • the fused aromatic ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound and the like
  • the heteroring-containing compound includes a carbazole derivative, a dibenzofuran derivative, a ladder-type furan compound, a pyrimidine derivative and the like, but the material is not limited thereto.
  • the dopant material includes an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound, a metal complex and the like.
  • the aromatic amine derivative is a fused aromatic ring derivative having a substituted or unsubstituted arylamino group and includes arylamino group-including pyrene, anthracene, crycene, peryflanthene and the like
  • the styrylamine compound is a compound in which substituted or unsubstituted arylamine is substituted with at least one arylvinyl group, and one, two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • styrylamine styryldiamine, styryltriamine, styryltetramine or the like is included, but the styrylamine compound is not limited thereto.
  • the metal complex includes an iridium complex, a platinum complex or the like, but is not limited thereto.
  • the electron transfer layer is a layer that receives electrons from an electron injection layer and transfers the electrons to a light emitting layer
  • a material capable of favorably receiving electrons from a cathode, moving the electrons to a light emitting layer, and having high mobility for the electrons is suitable.
  • Specific examples thereof include an Al complex of 8-hydroxyquinoline; a complex including Alq 3 ; an organic radical compound; a hydroxyflavon-metal complex and the like, but are not limited thereto.
  • the electron transfer layer may be used together with any desired cathode material as used according to existing technologies.
  • the suitable cathode material include common materials that have small work function, and in which an aluminum layer or a silver layer follows.
  • the cathode material includes cesium, barium, calcium, ytterbium and samarium, and in each case, an aluminum layer or a silver layer follows.
  • the electron injection layer is a layer that injects electrons from an electrode
  • the electron injection material is preferably a compound that has an ability to transfer electrons, has an electron injection effect from a cathode, has an excellent electron injection effect for a light emitting layer or a light emitting material, prevents excitons generated in the light emitting layer from moving to a hole injection layer, and in addition, has an excellent thin film forming ability.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidene methane, anthrone or the like, and derivatives thereof, a metal complex compound, a nitrogen-containing 5-membered ring derivative, and the like, but are not limited thereto.
  • the metal complex compound includes 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)berylium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtholato)gallium and the like, but is not limited thereto.
  • the organic light emitting device may be a top-emission type, a bottom-emission type or a dual-emission type depending on the materials used.
  • the double spiro structure compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to an organic light emitting device.
  • the double spiro structure compound represented by Chemical Formula 1 according to the present specification may be prepared through a multi-step chemical reaction.
  • the preparation of the compounds is described by the following synthesis examples and preparation examples.
  • the double spiro structure compound represented by Chemical Formula 1 may be prepared to compounds corresponding to Chemical Formula 2, Chemical Formula 3 and Chemical Formula 4 using methods and orders as in the following Reaction Formula 1-1, Reaction Formula 1-2 and Reaction Formula 1-3, respectively, and although not limited to such reactions, reaction formulae are simply described in order to illuminate the present invention.
  • compounds represented by Chemical Formulae 2 to 4 may be diversely prepared through varying L 1 to L 3 , Ar 1 to Ar 4 , Cy 1 , and X 1 to X 4 .
  • Compound 2-1-6 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that phenylfluoreneaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-7 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that biphenylfluoreneaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-10 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 1,1′-biphenylphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-15 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that bisbiphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-20 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that terphenylphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-25 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that orthobiphenylphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-26 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that orthobiphenylfluoreneaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-40 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 2-dibenzothiophenephenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-41 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 2-dibenzothiophenebiphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-42 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 2-dibenzothiophenefluoreneaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-46 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 2-dibenzofuranphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-47 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 2-dibenzofuranbiphenylaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-48 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 2-dibenzofuranfluoreneaminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-52 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that N-(4-(9H-carbazol-9-yl)phenyl)-9,9′-dimethyl-9H-fluoren-2-aminophenyl boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-54 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that N-(9,9′-dimethyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazol-3-1-Amino)phenyl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-64 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-(diphenylamino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-65 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-([1,1′-biphenyl]-4-yl(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-66 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-([1,1′:4′,1′′-terphenyl]-4-yl(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-67 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-(di([1,1′-biphenyl]-4-yl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-69 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-([1,1′-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-75 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-([1,1′-biphenyl]-2-yl([1,1′-biphenyl]-4-yl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-77 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-((9,9-dimethyl-9H-fluoren-2-yl)(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-81 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-([1,1′-biphenyl]-2-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-241 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-(dibenzo[b,d]thiophen-2-yl(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-242 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-(dibenzo[b,d]thiophen-4-yl(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-246 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-(dibenzo[b,d]furan-4-yl(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-315 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-((4′-(diphenylamino)-[1,1′-biphenyl]-4-yl)(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-316 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-((4-(diphenylamino)phenyl)(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-311 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-((4-([1,1′-biphenyl]-4-yl(phenyl)amino)phenyl)(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-318 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-((4-(di([1,1′-biphenyl]-4-yl)amino)phenyl)(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 2-1-320 (2-1) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that (4′-((4-([1,1′-biphenyl]-4-yl(9,9-dimethyl-9H-fluoren-2-yl)amino)phenyl)(phenyl)amino)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 3-1-2 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4-(4-([1,1′-biphenyl]-4-yl)-6-phenylpyridin-2-yl)phenyl)boronic acid was used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • Compound 3-1-6 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4-4-(9,9-dimethyl-9H-fluoren-2-yl)-6-phenylpyridin-2-yl)phenyl)boronic acid was used instead of (4-(4, 6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • Compound 3-1-9 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4-(4,6-di([1,1′-biphenyl]-4-yl)pyridin-2-yl)phenyl)boronic acid was used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • Compound 3-1-15 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4′-(4,6-diphenylpyridin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • Compound 3-1-16 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4′-(6-([1,1′-biphenyl]-4-yl)-4-phenylpyridin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • Compound 3-1-18 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4′-(4,6-di([1,1′-biphenyl]-4-yl)pyridin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • Compound 3-1-20 (3-5) was prepared in the same manner as in Preparation Example 2-1-1 preparing Compound 3-1-1 (3-5) except that (4′-(6-([1,1′-biphenyl]-4-yl)-4-(9,9-dimethyl-9H-fluoren-2-yl)pyridin-2-yl)-[1,1′-biphenyl]-4-yl)boronic acid was used instead of (4-(4,6-diphenylpyridin-2-yl)phenyl)boronic acid.
  • Compound 4-4-1 (4-5) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 4′-(benzo[d]oxazol-2-yl)biphenyl-4-ylboronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • Compound 4-4-2 (4-5) was prepared in the same manner as in Preparation Example 1-1 preparing Compound 2-1-1 (2-1) except that 4′-(benzo[d]thiazol-2-yl)biphenyl-4-ylboronic acid was used instead of (4-(diphenylamino)phenyl)boronic acid.
  • a glass substrate on which indium tin oxide (ITO) was coated as a thin film to a thickness of 1,000 ⁇ was placed in detergent-dissolved distilled water and ultrasonic cleaned.
  • ITO indium tin oxide
  • a product of Fischer Co. was used as the detergent, and as the distilled water, distilled water filtered twice with a filter manufactured by Millipore Co. was used.
  • the substrate was ultrasonic cleaned with solvents of isopropyl alcohol, acetone and methanol, then dried, and then transferred to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using oxygen plasma, and then transferred to a vacuum depositor.
  • a hole injection layer was formed by thermal vacuum depositing hexanitrile hexaazatriphenylene (HAT) of the following chemical formula to a thickness of 500 ⁇ .
  • HAT hexanitrile hexaazatriphenylene
  • a hole transfer layer was formed on the hole injection layer by vacuum depositing the following compound 4-4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) (300 ⁇ ), a material transferring holes.
  • an electron blocking layer was formed on the hole transfer layer to a film thickness of 100 ⁇ by vacuum depositing the following compound N-([1,1′-bisphenyl]-4-yl)-N-(4-(11-([1,1′-biphenyl]-4-yl)-11H-benzo[a]carbazol-5-yl)phenyl)-[1,1′-biphenyl]-4-amine (EB1)(100 ⁇ ).
  • a light emitting layer was formed on the electron blocking layer to a film thickness of 300 ⁇ by vacuum depositing BH and BD shown below in a weight ratio of 25:1.
  • An electron injection and transfer layer was formed on the light emitting layer to a thickness of 300 ⁇ by vacuum depositing the compound ET1 and the compound lithium quinolate (LiQ) in a weight ratio of 1:1.
  • a cathode was formed on the electron injection and transfer layer by depositing lithium fluoride (LiF) to a thickness of 12 ⁇ and aluminum to a thickness of 2,000 ⁇ in consecutive order.
  • An organic light emitting device was manufactured by maintaining, in the above-mentioned processes, the deposition rates of the organic materials at 0.4 ⁇ /sec to 0.7 ⁇ /sec, the deposition rates of the lithium fluoride and the aluminum of the cathode at 0.3 ⁇ /sec and 2 ⁇ /sec, respectively, and the degree of vacuum during the deposition at 2 ⁇ 10 ⁇ 7 torr to 5 ⁇ 10 ⁇ 6 torr.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-1 (2-1) was used instead of EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-6 (2-1) was used instead of EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-7 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-10 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-15 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-25 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-26 (2-1) was used instead of EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-40 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-41 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-42 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-47 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-48 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-52 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-54 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-64 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-66 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-67 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-69 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-75 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-77 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-241 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-242 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-246 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-315 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-316 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-318 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that Compound 2-1-320 (2-1) was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that a compound of the following HT1 was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that a compound of the following HT3 was used instead of Compound EB1.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that a compound of the following HT4 was used instead of Compound EB1.
  • the devices of Examples 1-1 to 1-32 using compounds having the double spiro structure compound represented by Chemical Formula 2 as the core had a lower driving voltage and enhanced efficiency compared to the devices of Comparative Example 1-1 to 1-4, and the device of Comparative Example 1 using a material of Compound EB1 as an electron blocking layer.
  • the double spiro structure compound according to the present specification had an excellent electron blocking ability and was capable of being used in an electron blocking layer of an organic light emitting device.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that the compounds of Examples 1-1 to 32 were used instead of NPB as the hole transfer layer.
  • the devices of Examples 2-1 to 2-32 using compounds having the double spiro structure represented by Chemical Formula 2 as the core had a lower driving voltage and enhanced efficiency compared to the devices of Comparative Examples 1-1 to 1-4, and the device of Comparative Example 1 using a material of NPB as the hole transfer layer.
  • the double spiro structure compound according to the present specification had an excellent hole transfer ability, and was capable of being used as a hole transfer layer in an organic light emitting device.
  • a glass substrate on which indium tin oxide (ITO) was coated as a thin film to a thickness of 1,000 ⁇ was placed in detergent-dissolved distilled water and ultrasonic cleaned.
  • ITO indium tin oxide
  • a product of Fischer Co. was used as the detergent, and as the distilled water, distilled water filtered twice with a filter manufactured by Millipore Co. was used.
  • the substrate was ultrasonic cleaned with solvents of isopropyl alcohol, acetone and methanol, then dried, and then transferred to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using oxygen plasma, and then transferred to a vacuum depositor.
  • a light emitting device was formed in order of m-MTDATA (60 nm)/TCTA (80 nm)/CBP+10% Ir(ppy) 3 (300 nm)/BCP (10 nm)/Alq 3 (30 nm)/LiF (1 nm)/Al (200 nm) using CBP as a host to manufacture an organic light emitting device.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-1 (3-5) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-2 (3-5) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-6 (3-5) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-9 (3-5) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-15 (3-5) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-16 (3-5) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-1-20 (3-5) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-1 (3-8) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-2 (3-8) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-6 (3-8) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-9 (3-8) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-16 (3-8) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-18 (3-8) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-2-20 (3-8) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-1 (3-11) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-2 (3-11) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-9 (3-11) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-15 (3-11) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-16 (3-11) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-18 (3-11) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-3-20 (3-11) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-4-2 (3-14) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-4-6 (3-14) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-4-9 (3-14) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-4-15 (3-14) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-4-16 (3-14) was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that Compound 3-4-20 (3-14) was used instead of CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH1 was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH2 was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH3 was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH4 was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH6 was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH7 was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 2 except that a compound of the following GH8 was used instead of Compound CBP.
  • An organic light emitting device was manufactured in the same manner as in Comparative Example 1 except that compounds of Examples 4-1 to 4-34 were used as in the following Table 10 instead of ET1 as the electron transfer layer.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Furan Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
US15/545,577 2015-02-16 2016-02-16 Double-spiro type compound and organic light-emitting device containing same Abandoned US20180002256A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
KR10-2015-0023506 2015-02-16
KR1020150023506A KR101837804B1 (ko) 2015-02-16 2015-02-16 이중스피로형 화합물 및 이를 포함하는 유기 발광 소자
PCT/KR2016/001559 WO2016133342A1 (ko) 2015-02-16 2016-02-16 이중스피로형 화합물 및 이를 포함하는 유기 발광 소자

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2016/001559 A-371-Of-International WO2016133342A1 (ko) 2015-02-16 2016-02-16 이중스피로형 화합물 및 이를 포함하는 유기 발광 소자

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US16/519,939 Division US11208368B2 (en) 2015-02-16 2019-07-23 Double-spiro type compound and organic light-emitting device containing same

Publications (1)

Publication Number Publication Date
US20180002256A1 true US20180002256A1 (en) 2018-01-04

Family

ID=56692368

Family Applications (2)

Application Number Title Priority Date Filing Date
US15/545,577 Abandoned US20180002256A1 (en) 2015-02-16 2016-02-16 Double-spiro type compound and organic light-emitting device containing same
US16/519,939 Active US11208368B2 (en) 2015-02-16 2019-07-23 Double-spiro type compound and organic light-emitting device containing same

Family Applications After (1)

Application Number Title Priority Date Filing Date
US16/519,939 Active US11208368B2 (en) 2015-02-16 2019-07-23 Double-spiro type compound and organic light-emitting device containing same

Country Status (7)

Country Link
US (2) US20180002256A1 (ko)
EP (1) EP3260438B1 (ko)
JP (1) JP6523465B2 (ko)
KR (1) KR101837804B1 (ko)
CN (1) CN107250101B (ko)
TW (1) TWI598324B (ko)
WO (1) WO2016133342A1 (ko)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11239425B2 (en) 2017-03-08 2022-02-01 Lg Chem, Ltd. Organic light emitting device
US11407718B2 (en) 2017-06-21 2022-08-09 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same
US11515478B2 (en) 2017-05-22 2022-11-29 Lg Chem Ltd. Compound and organic light emitting device using the same

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102145020B1 (ko) * 2017-10-23 2020-08-14 주식회사 엘지화학 신규한 고리 화합물 및 이를 이용한 유기발광 소자
KR102668884B1 (ko) * 2017-11-24 2024-05-27 솔루스첨단소재 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR102475856B1 (ko) * 2019-02-15 2022-12-08 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
KR102640224B1 (ko) * 2019-10-18 2024-02-22 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
CN114773286B (zh) * 2022-05-10 2024-02-20 长春海谱润斯科技股份有限公司 一种含氮杂环有机化合物及其有机发光器件
CN115960001B (zh) * 2022-10-24 2024-04-19 陕西莱特光电材料股份有限公司 有机化合物及包含其的电子元件和电子装置

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015086108A1 (de) * 2013-12-12 2015-06-18 Merck Patent Gmbh Materialien für elektronische vorrichtungen

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100428642B1 (ko) * 2001-04-27 2004-04-27 주식회사 엘지화학 이중 스피로형 유기물질
US6998487B2 (en) * 2001-04-27 2006-02-14 Lg Chem, Ltd. Double-spiro organic compounds and organic electroluminescent devices using the same
DE10135513B4 (de) 2001-07-20 2005-02-24 Novaled Gmbh Lichtemittierendes Bauelement mit organischen Schichten
CN1157461C (zh) * 2001-08-20 2004-07-14 清华大学 双螺环衍生物及其作为电致发光材料的应用
KR20110121147A (ko) * 2010-04-30 2011-11-07 다우어드밴스드디스플레이머티리얼 유한회사 신규한 유기 발광 화합물 및 이를 포함하는 유기 발광 소자
US9478749B2 (en) 2013-03-28 2016-10-25 Semiconductor Energy Laboratory Co., Ltd. Anthracene compound, light-emitting element, light-emitting device, electronic appliance, and lighting device
KR101560102B1 (ko) 2014-11-20 2015-10-13 주식회사 엘지화학 유기 발광 소자

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015086108A1 (de) * 2013-12-12 2015-06-18 Merck Patent Gmbh Materialien für elektronische vorrichtungen

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11239425B2 (en) 2017-03-08 2022-02-01 Lg Chem, Ltd. Organic light emitting device
US11515478B2 (en) 2017-05-22 2022-11-29 Lg Chem Ltd. Compound and organic light emitting device using the same
US11407718B2 (en) 2017-06-21 2022-08-09 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same

Also Published As

Publication number Publication date
TWI598324B (zh) 2017-09-11
US20190345082A1 (en) 2019-11-14
EP3260438A1 (en) 2017-12-27
WO2016133342A1 (ko) 2016-08-25
JP2018512375A (ja) 2018-05-17
EP3260438B1 (en) 2020-01-01
TW201636323A (zh) 2016-10-16
US11208368B2 (en) 2021-12-28
KR20160100698A (ko) 2016-08-24
KR101837804B1 (ko) 2018-03-12
JP6523465B2 (ja) 2019-06-05
CN107250101B (zh) 2020-03-31
CN107250101A (zh) 2017-10-13
EP3260438A4 (en) 2018-08-01

Similar Documents

Publication Publication Date Title
US11208368B2 (en) Double-spiro type compound and organic light-emitting device containing same
US10957857B2 (en) Multicyclic compound and organic light emitting device including the same
US10547008B2 (en) Organic light emitting device
US9882145B2 (en) Hetero ring compound and organic light emitting diode comprising same
US11718606B2 (en) Polycyclic compound and organic light emitting element comprising same
US10103336B2 (en) Heterocyclic compound and organic light-emitting element using same
US20190148650A1 (en) Organic Light Emitting Device
US9954181B2 (en) Hetero-cyclic compound and organic light emitting device comprising the same
US10800969B2 (en) Heterocyclic compound and organic light emitting element comprising same
US11075342B2 (en) Spiro-type compound and organic light emitting diode comprising same
US10738034B2 (en) Spiro compound and organic light-emitting device comprising same
US11737358B2 (en) Compound and organic light emitting device comprising same
US20200106017A1 (en) Novel compound and organic light emitting device using the same
US10991887B2 (en) Amine compound and organic light-emitting device comprising same
US10577355B2 (en) Hetero ring compound and organic luminescent element comprising same
US20170365788A1 (en) Amine compound and organic light emitting element comprising same
US20180248119A1 (en) Amine-based compound and organic light emitting device comprising same
US10421721B2 (en) Heterocyclic compound and organic light emitting device comprising same
US10035765B2 (en) Nitrogen-containing polycyclic compound and organic light emitting device using same
US11031560B2 (en) Compound and organic electronic element comprising same
US10730812B2 (en) Double spiro compound and organic light-emitting element comprising same
US9951270B2 (en) Multicyclic compound and organic electronic device using the same
US11261176B2 (en) Amine-based compound and organic light emitting device using the same
US20170186966A1 (en) Heterocyclic compound and organic light emitting device comprising same
US20240109884A1 (en) Novel compound and organic light emitting device comprising the same

Legal Events

Date Code Title Description
AS Assignment

Owner name: LG CHEM, LTD., KOREA, REPUBLIC OF

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:CHA, YONGBUM;KIM, JIN JOO;REEL/FRAME:043302/0020

Effective date: 20160303

STPP Information on status: patent application and granting procedure in general

Free format text: RESPONSE TO NON-FINAL OFFICE ACTION ENTERED AND FORWARDED TO EXAMINER

STPP Information on status: patent application and granting procedure in general

Free format text: NON FINAL ACTION MAILED

STPP Information on status: patent application and granting procedure in general

Free format text: RESPONSE TO NON-FINAL OFFICE ACTION ENTERED AND FORWARDED TO EXAMINER

STPP Information on status: patent application and granting procedure in general

Free format text: FINAL REJECTION MAILED

STPP Information on status: patent application and granting procedure in general

Free format text: RESPONSE AFTER FINAL ACTION FORWARDED TO EXAMINER

STPP Information on status: patent application and granting procedure in general

Free format text: ADVISORY ACTION MAILED

STPP Information on status: patent application and granting procedure in general

Free format text: DOCKETED NEW CASE - READY FOR EXAMINATION

STPP Information on status: patent application and granting procedure in general

Free format text: NON FINAL ACTION MAILED

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION