CN110577471A - 电致发光化合物和包括该电致发光化合物的电致发光装置 - Google Patents

电致发光化合物和包括该电致发光化合物的电致发光装置 Download PDF

Info

Publication number
CN110577471A
CN110577471A CN201910500620.4A CN201910500620A CN110577471A CN 110577471 A CN110577471 A CN 110577471A CN 201910500620 A CN201910500620 A CN 201910500620A CN 110577471 A CN110577471 A CN 110577471A
Authority
CN
China
Prior art keywords
group
formula
substituted
unsubstituted
independently selected
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201910500620.4A
Other languages
English (en)
Other versions
CN110577471B (zh
Inventor
刘璇根
朴熙俊
徐正大
玄瑞镕
金河延
尹石根
金淳基
李寅浩
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.)
P & H Tech Co Ltd
LG Display Co Ltd
Original Assignee
P & H Tech Co Ltd
LG Display Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by P & H Tech Co Ltd, LG Display Co Ltd filed Critical P & H Tech Co Ltd
Publication of CN110577471A publication Critical patent/CN110577471A/zh
Application granted granted Critical
Publication of CN110577471B publication Critical patent/CN110577471B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C07C15/24—Polycyclic condensed hydrocarbons containing two rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
    • C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
    • C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
    • C07C13/72—Spiro hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—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
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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
    • C07D219/08—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
    • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
    • C07D241/40—Benzopyrazines
    • C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D263/57—Aryl or substituted aryl radicals
    • 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
    • C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
    • 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
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D345/00—Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers

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)

Abstract

本发明提供一种下式1和式2之一的电致发光化合物。本发明的另一方面是一种电致发光装置，包括：第一电极；面向所述第一电极的第二电极；和位于所述第一电极和所述第二电极之间的至少一个有机材料层；其中所述至少一个有机材料层中的一个或多个包括所述的电致发光化合物。

Description

电致发光化合物和包括该电致发光化合物的电致发光装置
相关申请的交叉引用
本申请要求于2018年6月11日在韩国提交的韩国专利申请第10-2018-0066766号的权益，通过引用将上述专利申请作为整体结合在此。
技术领域
本公开内容涉及电致发光化合物，且更具体地，涉及具有改善的寿命和发光效率的电致发光化合物以及包括该电致发光化合物的电致发光装置。
背景技术
电致发光(EL)装置形成在透明基板上，并且可以在比操作其他显示装置(例如等离子体显示面板)所需的电压更低的电压(例如，10V或更低的电压)下操作。此外，EL装置具有较低的功耗和优异的色纯度。此外，由于EL装置可以发射红光、绿光和蓝光，因此EL装置被开发为下一代显示装置。
为了提供上述优点，需要具有高可靠性和高效率的材料，包括例如空穴注入材料、空穴传输材料、发光材料、电子传输材料或电子注入材料。然而，现有技术中的材料尚不充分，仍需要新材料。
近来，不仅需要藉由改变有机层中的材料来增强EL装置的性能，还需要藉由优化阳极与阴极之间的光学厚度来提高色纯度和发光效率。例如，在电极上可使用封盖层(capping layer)以提高EL装置的色纯度和发光效率。
需要开发用于增强EL装置的发光性能的装置结构和新材料。
发明内容
本发明涉及一种基本上消除了与相关传统技术的限制和缺点相关的一个或多个问题的EL化合物和包括该EL化合物的EL装置。
在下面的描述中阐明了本公开内容的附加特征和优点，这些特征和优点根据描述将显而易见，或者通过本发明的实践而清楚。通过本文以及附图中描述的特征可以实现和获得本发明的目的和其他优点。
为了实现根据本发明实施方式的目的的这些和其他优点，如本文所述，本发明的一个方面是式1或式2的电致发光化合物：[式1][式2]其中X1至X4的每一个独立地为N或CR’，其中R和R’的每一个独立地选自由氢、氘、氰基、羟基、卤素、C1至C10烷基、C6至C20芳基、和C3至C30杂芳基构成的组，其中L1和L2的每一个独立地选自单键、取代的或未取代的C6至C20次芳基、和取代的或未取代的C3至C30次杂芳基，并且其中Ar1和Ar2的每一个独立地选自由C6至C20芳基和C3至C30杂芳基构成的组。
本发明的另一方面是一种电致发光装置，包括：第一电极；面向第一电极的第二电极；以及位于第一电极和第二电极之间的至少一个有机材料层，其中所述至少一个有机材料层中的一个或多个包括所述电致发光化合物。
应当理解，前面的一般性描述和下面的详细描述都是示例性的和解释性的，意在对要求保护的本发明提供进一步的解释。
具体实施方式
现在将详细参照一些实施例和优选实施方式。
本公开内容的电致发光(EL)化合物由式1或式2表示。EL化合物被包括在EL装置的空穴传输层(HTL)中，使得EL装置的性质(例如发光效率、驱动特性或寿命)得到改善。此外，EL化合物可被包括在光效率增强层中，该光效率增强层形成在下电极或上电极的与EL装置的有机层相对的一侧上，从而使EL装置的光效率得到显著改善。结果，包括EL化合物的EL装置在发光效率、驱动电压、色纯度和寿命方面具有优势。
[式1]
[式2]
在式1和式2中，X1至X4的每一个独立地为N或CR’。R和R’的每一个独立地选自由氢、氘、氰基、羟基、卤素、C1至C10烷基、C6至C20芳基、和C3至C30杂芳基构成的组。
L1和L2的每一个独立地选自单键、取代的或未取代的C6至C20次芳基、和取代的或未取代的C3至C30次杂芳基。例如，L1和L2的每一个可选自式3a和式3b。
Ar1和Ar2的每一个独立地选自由C6至C20芳基、和C3至C30杂芳基构成的组。
Ar选自由取代的或未取代的C6至C20次芳基、和取代的或未取代的C3至C30次杂芳基构成的组。例如，Ar可以是式4。
[式4]
在式3a、式3b和式4中，X5至X7的每一个独立地为N或CR1。Y1和Y2的每一个独立地选自单键、O、S、Se、-R4-Si-R2-、R5-C-R3-。R1、R2、R3、R4和R5的每一个独立地选自由氢、氘、氰基、羟基、卤素、C1至C10烷基、C6至C20芳基、和C3至C30杂芳基构成的组。
“取代的或未取代的”中的术语“取代的”可以表示L1、L2、Ar、Ar1和Ar2的每一个可以进一步被至少一个取代基取代。在这种情况下，取代基可选自由氘、氰基、卤素、氨基、羟基、硝基、C1至C10烷基、C1至C10卤代烷基、C6至C20芳基、C3至C30杂芳基、C1至C10烷氧基、C1至C10烷基甲硅烷基、和C6至C20芳基甲硅烷基构成的组。
在本公开内容中，取代基的示例可以如下，但不限于此。
在本公开内容中，烷基可具有直链或支链结构。例如，烷基可选自由甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、仲丁基、1-甲基-丁基、1-乙基-丁基、戊基、正戊基、异戊基、新戊基、叔戊基、己基、正己基、1-甲基-戊基、和2-甲基-戊基构成的组，但不限于此。
芳基可具有单环或多环结构。例如，芳基可选自由苯基、联苯基、三联苯基、芪基、萘基、蒽基、菲基、芘基、苝基、并四苯基、基、芴基、次三苯基(triphenylenyl)、和荧蒽基，但不限于此。
杂芳基可包括杂原子，例如O、N或S。例如，杂芳基可选自由噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、恶唑基，恶二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔嗪基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并恶唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、苯并呋喃基、二苯并呋喃基、菲咯啉基、噻唑基、异恶二唑基、恶二唑基、噻二唑基、和吩噻嗪基构成的组，但不限于此。
芳基甲硅烷基中的芳基可以与上述芳基相同，卤素可以是氟、氯、溴或碘。
甲硅烷基可选自由三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基、乙烯基-二甲基甲硅烷基、丙基-二甲基甲硅烷基、三苯基甲硅烷基、二苯基甲硅烷基、和苯基甲硅烷基构成的组，但不限于此。
作为取代基的卤素可以是氟、氯或溴。
由于结构上的区别，本公开内容的式1或式2的EL化合物可用于EL装置的有机层。例如，作为有机化合物的EL化合物可以用作空穴传输材料或在EL装置的电极侧形成的光效率增强层的材料。
例如，式1或式2的EL化合物可以是式5的化合物之一，但不限于此。
[式5]
如上所述，本公开内容的EL化合物由于结构和取代基而具有特定的性质。例如，藉由将在空穴注入材料、空穴传输材料、发光材料或电子传输材料中所包括的取代基进行取代为本公开内容的EL化合物，EL化合物可以提供所需的性质。具体地，EL化合物可以在有或没有其他化合物的情况下用于空穴传输材料。此外，EL化合物可用于光效率增强层，其可被称为封盖层(CPL)。
EL化合物可以通过常规方法应用于EL装置。
根据示例性实施方式的EL装置可具有包括第一电极、第二电极、和二者之间的有机材料层的结构。除用于有机材料层的EL化合物之外，传统的制造方法和材料可用于EL装置。
EL装置的有机材料层可具有单层结构或包括至少两层的多层结构。例如，有机材料层可包括空穴注入层(HIL)、空穴传输层(HTL)、发光材料层(EML)、电子传输层(ETL)、和电子注入层(EIL)，但不限于此。有机材料层可进一步包括电子阻挡层(EBL)和空穴阻挡层(HBL)的至少一者。有机材料层可包括比上述多层结构更少或更多的层。
因此，在本公开内容的EL装置中，有机材料层可包括空穴传输层和空穴注入传输层的至少一者，并且空穴传输层和空穴注入层的至少一者可包括式1或式2的EL化合物。
EL装置可包括基板、作为阳极的第一电极、有机材料层、作为阴极的第二电极、和光效率增强层。光效率增强层可以形成在底部发光型EL装置中的第一电极的下表面上，或者可以形成在顶部发光型EL装置中的第二电极的上表面上。
在顶部发光型EL装置中，来自发光材料层的光通过阴极(即第二电极)发射并穿过光效率增强层(即封盖层(CPL))，光效率增强层包括具有相对较高折射率的本公开内容的化合物，使得光的波长得到放大(增加)并且光效率得到改善。此外，在底部发光型EL装置中，光效率增强层包括本公开内容的化合物，藉由相同的原理，使得提高光效率。
将更详细地进一步解释EL装置的有机材料层的结构。
EL装置可通过以下方法来制造：使用诸如溅射、电子束蒸发、物理气相沉积(PVD)之类的沉积方法在基板上沉积金属、具有导电性的金属氧化物或其合金来形成阳极；在阳极上形成包括空穴注入层、空穴传输层、发光材料层和电子传输层的有机材料层；和在有机材料层上沉积能够用作阴极的材料。
或者，可以通过顺序地沉积阴极材料、有机材料和阳极材料来制造EL装置。有机材料层可以是包括空穴注入层、空穴传输层、发光材料层和电子传输层在内的多层结构，但不限于此。有机材料层可以是单层结构。此外，有机材料层可以通过例如旋涂工艺、浸涂工艺、刮刀工艺、丝网印刷工艺、喷墨印刷工艺或热转移工艺的溶液工艺形成。
用于阳极的材料可具有相对较高的功函，以促进空穴注入到有机材料层。例如，用于阳极的材料可以是金属，诸如钒、铬、铜、锌或金；它们的合金；金属氧化物，诸如氧化锌、氧化铟、氧化铟锡(ITO)或氧化铟锌(IZO)；金属和金属氧化物的组合，诸如ZnO:Al或SnO2:Sb；和导电聚合物，诸如聚(3-甲基噻吩)、聚[3,4-(乙烯-1,2-二氧基)噻吩](PEDT)、聚吡咯或聚苯胺，但不限于此。
用于阴极的材料可具有相对较低的功函，以促进电子注入到有机材料层。例如，用于阴极的材料可以是金属，诸如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡或铅；它们的合金；或多结构材料，诸如LiF/Al或LiO2/Al，但不限于此。
以低电压有效地从阳极接收空穴的空穴注入材料用于空穴注入层。空穴注入材料的最高占据分子轨道(HOMO)介于阳极的功函与相邻有机材料层的HOMO之间。例如，空穴注入材料可以是金属卟啉、低聚噻吩、芳胺基有机材料、六腈六氮杂苯并菲、喹吖啶酮基有机材料、苝基有机材料、蒽醌、聚苯胺基导电聚合物、或聚噻吩基导电聚合物，但不限于此。
从空穴注入层或阳极接收空穴并将空穴提供到发光材料层中的空穴传输材料用于空穴传输层。即，空穴传输材料具有高的空穴迁移率。例如，空穴传输材料可以是芳胺基有机材料、导电聚合物、包含共轭部分和非共轭部分的嵌段共聚物、或本公开内容的化合物。具体地，空穴传输层包括本公开内容的化合物，使得EL装置的性质(例如，驱动电压、发光效率和寿命)得到进一步改善。
将分别来自空穴传输层和电子传输层的空穴和电子结合在一起并发射可见光的发光材料用于发光材料层。发光材料可以是荧光化合物或磷光化合物。例如，发光材料可以是8-羟基-喹啉-铝配合物(Alq3)、咔唑基化合物、二聚的苯乙烯基化合物、BAlq、10-羟基-苯并喹啉金属化合物、苯并恶唑基化合物、苯并噻唑基化合物、苯并咪唑基化合物、聚(对苯基次乙烯)基聚合物、螺环化合物、聚芴或红荧烯，但不限于此。
将电子从阴极有效地提供到发光材料层中的电子传输材料用于电子传输层。即，电子传输材料具有高的电子迁移率。例如，电子传输材料可以是Alq3、有机自由基化合物、或羟基黄酮-金属配合物，但不限于此。
根据EL装置中的材料，本公开内容的EL装置可以是顶部发光型、底部发光型或双面发光型。
此外，本公开内容的EL化合物可以用于有机电子装置，诸如有机太阳能电池、有机光导体或有机晶体管，其原理与EL装置相同。
1.化合物3的合成
将甲苯(300mL)加入到4-(萘-2-基)苯胺(10g，0.045mol，Mascot.)、4-碘联苯(26.82g，0.95mol，sigma aldrich)、叔丁醇钠(17.53g，0.18mol，sigma aldrich)、作为催化剂的Pd(dba)2(1.31g，0.0023mol，sigma aldrich)、和三叔丁基膦(0.92g，0.0046mol，sigma aldrich)的混合物中，并在100℃的温度下搅拌4小时。反应完成后，通过对混合物进行萃取和柱精制，得到化合物3(18g，收率：75.3％)。
H-NMR(200MHz,CDCl3):δppm,1H(7.92/d,7.73/d,7.58/s)2H(8.00/d,7.59/m,7.41/m)4H(7.52/d,7.51/m)6H(7.54/d,6.69/d),LC/MS:m/z＝523[(M+1)+]
2.化合物9的合成
(1)化合物9-1
将甲苯(300mL)加入到2-(4-溴苯基)萘(10g，0.045mol，TCI)、4-(萘-2-基)苯胺(14.05g，0.050mol，Mascot.)、叔丁醇钠(8.77g，0.091mol，sigma aldrich)、Pd(dba)2(1.31g，0.0023mol，sigma aldrich)、和三叔丁基膦(0.92g，0.0046mol，sigma aldrich)的混合物中，并在100℃的温度下搅拌4小时。反应完成后，通过对混合物进行萃取和柱精制，得到化合物9-1(14.4g，收率：74.9％)。
(2)化合物9
将甲苯(200mL)加入到化合物9-1(10g，0.023mol)、4-碘联苯(7.31g，0.026mol，sigma aldrich)、叔丁醇钠(4.56g，0.047mol，sigma aldrich)、Pd(dba)2(0.68g，0.0012mol，sigma aldrich)、和三叔丁基膦(0.48g，0.0024mol，sigma aldrich)的混合物中，并在100℃的温度下搅拌5小时。反应完成后，通过对混合物进行萃取和柱精制，得到化合物9(10.2g，收率：74.9％)。
H-NMR(200MHz,CDCl3):δppm,1H(7.41/m)2H(7.92/d,7.73/d,7.58/d,7.52/d,7.51/m)4H(8.00/d,7.59/m)6H(7.54/d,6.69/d),LC/MS:m/z＝573[(M+1)+]
3.化合物18的合成
(1)化合物18-1
将甲苯(300mL)加入到3-溴二苯并呋喃(20g，0.081mol，TCI)、4-氨基联苯(16.44g，0.097mol，sigma aldrich)、叔丁醇钠(15.56g，0.16mol，sigma aldrich)、Pd(dba)2(2.33g，0.004mol，sigma aldrich)和三叔丁基膦(1.64g，0.008mol，sigmaaldrich)的混合物中，并在100℃的温度下搅拌3小时。反应完成后，通过对混合物进行萃取和柱精制，得到化合物18-1(19.2g，收率：70.7％)。
(2)化合物18
将甲苯(150mL)加入到2-(4-溴苯基)萘(10g，0.035mol，TCI)、化合物18-1(13.03g，0.038mol)、叔丁醇钠(6.79g，0.070mol，sigma aldrich)、Pd(dba)2(1.02g，0.0018mol，sigma aldrich)、和三叔丁基膦(0.71g，0.0035mol，sigma aldrich)的混合物中，并在100℃的温度下搅拌12小时。反应完成后，通过对混合物进行萃取和柱精制，得到化合物18(14.4g，收率：75.8％)。
H-NMR(200MHz,CDCl3):δppm,1H(7.92/d,7.89/d,7.73/d,7.66/d,7.64/d,7.58/s,7.43/s,7.41/m,7.38/m,7.32/m,6.33/d)2H(8.00/d,7.59/m,7.52/d,7.51/m)4H(7.54/d,6.69/d),LC/MS:m/z＝537[(M+1)+]
4.化合物51的合成
(1)化合物51-1
将甲苯(150mL)加入到4-溴联苯(10g，0.040mol，sigma aldrich)、4-氨基联苯(7.53g，0.044mol，sigma aldrich)、叔丁醇钠(7.78g，0.081mol，sigma aldrich)、Pd(dba)2(1.16g，0.002mol，sigma aldrich)、和三叔丁基膦(0.82g，0.004mol，sigmaaldrich)的混合物中，并在100℃的温度下搅拌5小时。反应完成后，通过对混合物进行萃取和柱精制，得到化合物51-1(10.5g，收率：80.7％)。
(2)化合物51-2
将甲苯(150mL)和水(40mL)加入到2,7-二溴-9,9-二甲基-9H-芴(10g，0.039mol，sigma aldrich)、2-萘基硼酸(7.51g，0.047mol，sigma aldrich)、碳酸钾(16.45g，0.12mol，sigma aldrich)、和Pd(PPh3)4(2.29g，0.002mol，sigma aldrich)的混合物中，并在60℃的温度下搅拌4小时。反应完成后，通过对混合物进行萃取和柱精制，得到化合物51-2(12g，收率：75.7％)。
(3)化合物51
将甲苯(150mL)加入到化合物51-2(10g，0.025mol)、化合物51-1(8.85g，0.027mol)、叔丁醇钠(4.81g，0.050mol，sigma aldrich)、Pd(dba)2(0.72g，0.0013mol，sigma aldrich)、和三叔丁基膦(0.51g，0.0025mol，sigma aldrich)的混合物中，并在100℃的温度下搅拌12小时。反应完成后，通过对混合物进行萃取和柱精制，得到化合物51(12g，收率：74.8％)。
H-NMR(200MHz,CDCl3):δppm,1H(7.93/d,7.92/d,7.77/s,7.73/d,7.63/d,7.62/d,7.58/s,6.75/s,6.58/d)2H(8.00/d,7.59/m,7.41/m)3H(6H(1.72/s)4H(7.54/d,7.52/d,7.51/m,6.69/d)6H(1.72/s),LC/MS:m/z＝639[(M+1)+]
5.化合物71的合成
(1)化合物71-1
将甲苯(200mL)和水(50mL)加入到2,4,6-三碘吡啶(10g，0.028mol，Mascot.)、6-溴-3-吡啶基硼酸(18.34g，0.09mol，sigma aldrich)、碳酸钾(27.48g，0.0198mol，sigmaaldrich)、和Pd(PPh3)4(1.64g，0.0014mol，sigma aldrich)的混合物中，并在60℃的温度下搅拌8小时。反应完成后，通过对混合物进行萃取和柱精制，得到化合物71-1(12g，收率：77.2％)。
(2)化合物71
将甲苯(200mL)和水(50mL)加入到化合物71-1(10g，0.018mol)、2-萘基硼酸(10.06g，0.058mol，sigma aldrich)、碳酸钾(17.69g，0.128mol，sigma aldrich)、和Pd(PPh3)4(1.06g，0.0009mol，sigma aldrich)的混合物中，并在60℃的温度下搅拌8小时。反应完成后，通过对混合物进行萃取和柱精制，得到化合物71(9.3g，收率：73.8％)。
H-NMR(200MHz,CDCl3):δppm,1H(8.78/s,8.03/d,7.69/d)2H(9.29/s,8.62/s,8.20/d,8.06/d)3H(8.85/s,8.38/d,7.95/d)6H(8.00/d,7.59/m),LC/MS:m/z＝688[(M+1)+]
[装置]
在玻璃基板上形成ITO透明电极，并将其图案化为具有2mm×2mm的发光面积。清洁包括ITO透明电极的基板。将基板装入基础压力为1×10-6托的真空室中，并如下沉积有机材料和金属。
本公开内容的化合物用于空穴传输层，并制造具有以下结构的蓝色EL装置：ITO；HIL(式6，5nm)；HTL(100nm)；EBL(式7，10nm)；EML(主体(式8)：掺杂剂(式9)，20nm)；ETL(式10：Liq(50重量％掺杂)，30nm)；EIL(LiF，1nm)；和Al(100nm)。
[实施例1至实施例9(Ex1至Ex9)]
化合物3、9、18、23、32、45、51、93和95用于形成HTL。
[比较例(Ref)]
式11的化合物用于形成HTL。
[式6]
[式7]
[式8]
[式9]
[式10]
[式11]
通过源表(型号237，Keithley)和亮度计(PR-650，Photo Research)测量实施例1至实施例9和比较例的EL装置的特性，例如驱动电压(V)、电流效率(cd/A)、量子效率(QE)和色坐标指数(CIEx，CIEy)，并在表1中列出。电流密度为10mA/cm2的电压被定义为驱动电压。
表1
V cd/A QE(％) CIEx CIEy
实施例1 3.94 7.87 6.70 0.144 0.153
实施例2 4.02 7.77 6.58 0.144 0.154
实施例3 4.13 7.64 6.42 0.144 0.155
实施例4 4.20 7.39 6.10 0.145 0.156
实施例5 4.04 7.78 6.58 0.144 0.154
实施例6 4.16 7.48 6.20 0.145 0.155
实施例7 4.22 7.40 6.12 0.145 0.155
实施例8 4.17 7.51 6.25 0.144 0.154
实施例9 4.19 7.45 6.20 0.145 0.154
参考 4.20 6.20 5.10 0.145 0.156
如表1中所示，与比较例的EL装置相比，实施例1至实施例9的在HTL中包括所述化合物的EL装置的发光特性(例如发光效率和量子效率)显著更优。
在不脱离本发明的精神或范围的情况下，本发明可进行各种修改和变化，这对于本领域普通技术人员来说是显而易见的。因而，本发明意在覆盖落入所附权利要求范围及其等效范围内的本发明的修改和变化。

Claims (20)

1.一种电致发光化合物，其为式1或式2：
[式1]
[式2]
其中X1至X4的每一个独立地为N或CR’，
其中R和R’的每一个独立地选自由氢、氘、氰基、羟基、卤素、C1至C10烷基、C6至C20芳基、和C3至C30杂芳基构成的组，
其中L1和L2的每一个独立地选自单键、取代的或未取代的C6至C20次芳基、和取代的或未取代的C3至C30次杂芳基，
其中Ar选自由取代的或未取代的C6至C20次芳基、和取代的或未取代的C3至C30次杂芳基构成的组，并且
其中Ar1和Ar2的每一个独立地选自由C6至C20芳基和C3至C30杂芳基构成的组。
2.根据权利要求1所述的电致发光化合物，其中L1和L2的每一个选自式3a和式3b，并且Ar由式4表示：
[式4]
其中X5至X7的每一个独立地为N或CR1，
其中Y1和Y2独立地选自单键、O、S、Se、-R4-Si-R2-、R5-C-R3-，并且
其中R1、R2、R3、R4和R5的每一个独立地选自由氢、氘、氰基、羟基、卤素、C1至C10烷基、C6至C20芳基、和C3至C30杂芳基构成的组。
3.根据权利要求1所述的电致发光化合物，其中L1、L2、Ar、Ar1和Ar2的每一个的取代基独立地选自由氘、氰基、卤素、氨基、羟基、硝基、C1至C10烷基、C1至C10卤代烷基、C6至C20芳基、C3至C30杂芳基、C1至C10烷氧基、C1至C10烷基甲硅烷基、和C6至C20芳基甲硅烷基构成的组。
4.根据权利要求1所述的电致发光化合物，其中所述电致发光化合物选自式5：
[式5]
5.一种电致发光装置，包括：
第一电极；
面向所述第一电极的第二电极；和
位于所述第一电极和所述第二电极之间的至少一个有机材料层，
其中所述至少一个有机材料层中的一个或多个包括权利要求1所述的电致发光化合物。
6.根据权利要求5所述的电致发光装置，其中所述至少一个有机材料层包括电子注入层、电子传输层、空穴注入层、空穴传输层、电子阻挡层、空穴阻挡层、和发光材料层中的至少一者。
7.根据权利要求6所述的电致发光装置，其中所述空穴传输层包括所述电致发光化合物。
8.根据权利要求5所述的电致发光装置，进一步包括：
位于所述第一电极和所述第二电极之一的一侧上的光效率增强层，所述光效率增强层相对地定位成与所述有机材料层相对，
其中所述光效率增强层包括所述电致发光化合物。
9.根据权利要求8所述的电致发光装置，其中所述光效率增强层形成在所述第一电极的下表面和所述第二电极的上表面的至少一个上。
10.根据权利要求5所述的电致发光装置，其中L1和L2的每一个选自式3a和式3b，并且Ar由式4表示：
[式4]
其中X5至X7的每一个独立地为N或CR1，
其中Y1和Y2独立地选自单键、O、S、Se、-R4-Si-R2-、R5-C-R3-，并且
其中R1、R2、R3、R4和R5的每一个独立地选自由氢、氘、氰基、羟基、卤素、C1至C10烷基、C6至C20芳基、和C3至C30杂芳基构成的组。
11.根据权利要求5所述的电致发光装置，其中L1、L2、Ar、Ar1和Ar2的每一个的取代基独立地选自由氘、氰基、卤素、氨基、羟基、硝基、C1至C10烷基、C1至C10卤代烷基、C6至C20芳基、C3至C30杂芳基、C1至C10烷氧基、C1至C10烷基甲硅烷基、和C6至C20芳基甲硅烷基构成的组。
12.根据权利要求5所述的电致发光装置，其中所述电致发光化合物选自式5：
[式5]
13.根据权利要求1所述的电致发光化合物，其为式1，
其中X1至X4的每一个独立地为N或CR’，
其中R和R’的每一个独立地选自由氢、氘、氰基、羟基、卤素、C1至C10烷基、C6至C20芳基、和C3至C30杂芳基构成的组，
其中L1选自单键、取代的或未取代的C6至C20次芳基、和取代的或未取代的C3至C30次杂芳基，并且
其中Ar1和Ar2的每一个独立地选自由C6至C20芳基和C3至C30杂芳基构成的组。
14.根据权利要求1所述的电致发光化合物，其为式1，
其中X1至X4的每一个独立地为N或CR’，
其中R和R’的每一个独立地选自由氢、氘、氰基、羟基、卤素、C1至C10烷基、C6至C20芳基、和C3至C30杂芳基构成的组，
其中L2选自单键、取代的或未取代的C6至C20次芳基、和取代的或未取代的C3至C30次杂芳基，
其中Ar选自由取代的或未取代的C6至C20次芳基、和取代的或未取代的C3至C30次杂芳基构成的组，并且
其中Ar1和Ar2的每一个独立地选自由C6至C20芳基和C3至C30杂芳基构成的组。
15.根据权利要求5所述的电致发光装置，其中所述电致发光化合物为式1，
其中X1至X4的每一个独立地为N或CR’，
其中R和R’的每一个独立地选自由氢、氘、氰基、羟基、卤素、C1至C10烷基、C6至C20芳基、和C3至C30杂芳基构成的组，
其中L1选自单键、取代的或未取代的C6至C20次芳基、和取代的或未取代的C3至C30次杂芳基，并且
其中Ar1和Ar2的每一个独立地选自由C6至C20芳基和C3至C30杂芳基构成的组。
16.根据权利要求5所述的电致发光装置，其中所述电致发光化合物为式2，
其中X1至X4的每一个独立地为N或CR’，
其中R和R’的每一个独立地选自由氢、氘、氰基、羟基、卤素、C1至C10烷基、C6至C20芳基、和C3至C30杂芳基构成的组，
其中L2选自单键、取代的或未取代的C6至C20次芳基、和取代的或未取代的C3至C30次杂芳基，
其中Ar选自由取代的或未取代的C6至C20次芳基、和取代的或未取代的C3至C30次杂芳基构成的组，并且
其中Ar1和Ar2的每一个独立地选自由C6至C20芳基和C3至C30杂芳基构成的组。
17.根据权利要求13的所述电致发光化合物，其中R和R’是氢。
18.根据权利要求14的所述电致发光化合物，其中R和R’是氢。
19.根据权利要求15所述的电致发光装置，其中R和R’是氢。
20.根据权利要求16所述的电致发光装置，其中R和R’是氢。
CN201910500620.4A 2018-06-11 2019-06-11 电致发光化合物和包括该电致发光化合物的电致发光装置 Active CN110577471B (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2018-0066766 2018-06-11
KR1020180066766A KR20190140233A (ko) 2018-06-11 2018-06-11 유기발광 화합물 및 이를 포함하는 유기발광소자

Publications (2)

Publication Number Publication Date
CN110577471A true CN110577471A (zh) 2019-12-17
CN110577471B CN110577471B (zh) 2023-09-29

Family

ID=68764167

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201910500620.4A Active CN110577471B (zh) 2018-06-11 2019-06-11 电致发光化合物和包括该电致发光化合物的电致发光装置

Country Status (3)

Country Link
US (1) US11469378B2 (zh)
KR (1) KR20190140233A (zh)
CN (1) CN110577471B (zh)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111995530A (zh) * 2019-05-27 2020-11-27 东进世美肯株式会社 覆盖层用有机化合物及包含其的有机发光器件
CN112538060A (zh) * 2019-09-23 2021-03-23 东进世美肯株式会社 全新的覆盖层用有机化合物以及包含上述覆盖层用有机化合物的有机发光元件
CN112952019A (zh) * 2021-02-03 2021-06-11 烟台显华光电材料研究院有限公司 一种有机电致发光器件及包含该器件的显示装置
CN112952020A (zh) * 2021-02-03 2021-06-11 烟台显华光电材料研究院有限公司 一种有机电致发光器件及包含该器件的显示装置
WO2021135542A1 (zh) * 2019-12-30 2021-07-08 陕西莱特光电材料股份有限公司 含氮化合物、电子元件和电子装置
WO2021143246A1 (zh) * 2020-01-19 2021-07-22 广州华睿光电材料有限公司 有机电致发光器件和含稠环的芳胺类化合物
CN113745436A (zh) * 2020-05-29 2021-12-03 乐金显示有限公司 有机发光装置
CN114685396A (zh) * 2022-04-02 2022-07-01 京东方科技集团股份有限公司 一种光提取材料、光提取层、发光器件和显示装置
CN115260157A (zh) * 2021-04-29 2022-11-01 常州强力昱镭光电材料有限公司 立体环喹喔啉化合物、有机电致发光器件、显示装置及应用

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020111253A1 (ja) 2018-11-30 2020-06-04 出光興産株式会社 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、及び、電子機器
KR102470622B1 (ko) 2019-10-04 2022-11-24 (주)랩토 3차 아민 유도체 및 이를 포함한 유기 전계 발광 소자
EP4129972A4 (en) 2020-03-31 2024-04-17 Idemitsu Kosan Co.,Ltd. COMPOUND, MATERIAL FOR ORGANIC ELECTROLUMINESCENT ELEMENTS, ORGANIC ELECTROLUMINESCENT ELEMENT AND ELECTRONIC DEVICE
KR102711427B1 (ko) * 2020-06-02 2024-09-26 삼성에스디아이 주식회사 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치
KR102377867B1 (ko) * 2020-08-14 2022-03-24 엘티소재주식회사 유기 발광 소자 및 유기물층 형성용 조성물
CN116326250A (zh) * 2020-10-20 2023-06-23 株式会社Lg化学 有机发光器件
KR20230113545A (ko) 2020-11-27 2023-07-31 이데미쓰 고산 가부시키가이샤 화합물, 유기 전기발광 소자용 재료, 유기 전기발광 소자 및 전자 기기
CN116472794A (zh) 2020-11-27 2023-07-21 出光兴产株式会社 化合物、有机电致发光元件用材料、有机电致发光元件和电子设备
KR20220120506A (ko) * 2021-02-22 2022-08-30 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
EP4299574A4 (en) * 2021-11-10 2024-01-03 Lg Chem, Ltd. NOVEL COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING SAME
KR20230103320A (ko) * 2021-12-31 2023-07-07 엘지디스플레이 주식회사 전계발광 표시장치

Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1013740A2 (en) * 1998-12-25 2000-06-28 Konica Corporation Electroluminescent material, electroluminescent element and color conversion filter
JP2000230132A (ja) * 1998-12-07 2000-08-22 Sony Corp ビス（アミノスチリル）ベンゼン化合物及びその合成中間体、並びにこれらの製造方法
JP2004231547A (ja) * 2003-01-29 2004-08-19 Idemitsu Kosan Co Ltd 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子
WO2007125714A1 (ja) * 2006-04-26 2007-11-08 Idemitsu Kosan Co., Ltd. 芳香族アミン誘導体及びそれらを用いた有機エレクトロルミネッセンス素子
WO2009145016A1 (ja) * 2008-05-29 2009-12-03 出光興産株式会社 芳香族アミン誘導体及びそれらを用いた有機エレクトロルミネッセンス素子
JP2012097091A (ja) * 2007-12-03 2012-05-24 Semiconductor Energy Lab Co Ltd カルバゾール誘導体、カルバゾール誘導体を用いた発光素子、照明装置、発光装置、および電子機器
JP5420310B2 (ja) * 2008-05-16 2014-02-19 株式会社半導体エネルギー研究所 トリアリールアミン誘導体、発光物質、発光素子、発光装置及び電子機器
US20140197381A1 (en) * 2013-01-11 2014-07-17 Se-Hun Kim Organic light-emitting diode comprising amine-based compounds and pyrene-based compounds
KR20150023657A (ko) * 2012-06-06 2015-03-05 메르크 파텐트 게엠베하 유기 전자 소자용 페난트렌 화합물
KR101530049B1 (ko) * 2014-10-24 2015-06-18 덕산네오룩스 주식회사 유기전기소자용 조성물을 이용한 디스플레이 장치 및 유기전기소자
US20150295181A1 (en) * 2012-11-12 2015-10-15 Merck Patent Gmbh Materials for electronic devices
US20160043325A1 (en) * 2011-01-11 2016-02-11 Mitsubishi Chemical Corporation Composition for organic electroluminescent element, organic electroluminescent element, display and lighting
WO2016032137A1 (ko) * 2014-08-29 2016-03-03 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
WO2016190600A1 (ko) * 2015-05-27 2016-12-01 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20160149975A (ko) * 2015-06-17 2016-12-28 삼성디스플레이 주식회사 유기 전계 발광 소자용 재료 및 이를 포함하는 유기 전계 발광 소자
WO2017146466A1 (ko) * 2016-02-23 2017-08-31 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
US20170288147A1 (en) * 2016-03-30 2017-10-05 Samsung Display Co., Ltd. Organic light emitting device
KR20180044799A (ko) * 2016-10-21 2018-05-03 삼성디스플레이 주식회사 모노아민 화합물 및 이를 포함하는 유기 전계 발광 소자

Family Cites Families (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009085344A2 (en) * 2007-12-28 2009-07-09 Universal Display Corporation Dibenzothiophene-containing materials in phosphorescent light emitting diodes
KR101741415B1 (ko) * 2009-04-29 2017-05-30 롬엔드하스전자재료코리아유한회사 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자
KR101094287B1 (ko) * 2009-10-09 2011-12-19 삼성모바일디스플레이주식회사 유기 발광 표시 장치
KR20110049554A (ko) * 2009-11-05 2011-05-12 엘지디스플레이 주식회사 청색 형광 화합물 및 이를 포함하는 유기전계발광소자
WO2013039914A1 (en) * 2011-09-12 2013-03-21 Nitto Denko Corporation Efficient organic light-emitting diodes and fabrication of the same
US9917281B2 (en) * 2012-09-07 2018-03-13 Nitto Denko Corporation Top-emitting white organic light-emitting diodes having improved efficiency and stability
US10741772B2 (en) * 2014-08-29 2020-08-11 Samsung Electronics Co., Ltd. Organic light-emitting device
KR101620092B1 (ko) * 2014-11-06 2016-05-13 삼성디스플레이 주식회사 유기 발광 소자 및 그 제조방법
KR102304721B1 (ko) * 2014-11-21 2021-09-27 삼성디스플레이 주식회사 아민계 화합물 및 이를 포함한 유기 발광 소자
JP6661289B2 (ja) * 2015-07-08 2020-03-11 三星ディスプレイ株式會社Ｓａｍｓｕｎｇ Ｄｉｓｐｌａｙ Ｃｏ．，Ｌｔｄ． 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子
US10439146B2 (en) * 2015-08-07 2019-10-08 Semiconductor Energy Laboratory Co., Ltd. Organic compound, light-emitting element, light-emitting device, electronic device, and lighting device
US10270041B2 (en) * 2015-08-28 2019-04-23 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, electronic device, and lighting device
KR102445081B1 (ko) * 2015-09-24 2022-09-20 엘지디스플레이 주식회사 유기전계발광소자
KR101806464B1 (ko) * 2015-11-19 2017-12-07 (주)랩토 피리딜기가 결합된 피리미딘 유도체 및 이를 이용한 유기 전계 발광 소자
KR102617840B1 (ko) * 2015-11-26 2023-12-26 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR102076884B1 (ko) * 2015-12-08 2020-02-13 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
KR20170068705A (ko) * 2015-12-09 2017-06-20 삼성디스플레이 주식회사 유기 발광 소자
KR102579753B1 (ko) * 2015-12-22 2023-09-19 삼성디스플레이 주식회사 유기 발광 소자
WO2018016742A1 (ko) * 2016-07-20 2018-01-25 주식회사 엘지화학 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
US10388900B2 (en) * 2016-07-28 2019-08-20 Semiconductor Energy Laboratory Co., Ltd. Light-emitting element, light-emitting device, electronic device, and lighting device
US11205755B2 (en) * 2016-07-29 2021-12-21 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using same, and electronic device thereof
EP3312166B1 (en) 2016-10-21 2019-11-27 Samsung Display Co., Ltd. Monoamine compound and organic electroluminescence device including the same
KR102378356B1 (ko) * 2017-08-09 2022-03-25 삼성디스플레이 주식회사 유기 발광 소자 및 이를 포함한 전자 장치
KR102697017B1 (ko) * 2017-09-22 2024-08-22 듀폰스페셜티머터리얼스코리아 유한회사 복수 종의 호스트 재료 및 이를 포함하는 유기 전계 발광 소자
KR102648001B1 (ko) * 2017-11-24 2024-03-14 가부시키가이샤 한도오따이 에네루기 켄큐쇼 다이벤조[c,g]카바졸 유도체, 발광 소자, 발광 장치, 전자 기기, 및 조명 장치

Patent Citations (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2000230132A (ja) * 1998-12-07 2000-08-22 Sony Corp ビス（アミノスチリル）ベンゼン化合物及びその合成中間体、並びにこれらの製造方法
EP1013740A2 (en) * 1998-12-25 2000-06-28 Konica Corporation Electroluminescent material, electroluminescent element and color conversion filter
JP2004231547A (ja) * 2003-01-29 2004-08-19 Idemitsu Kosan Co Ltd 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子
WO2007125714A1 (ja) * 2006-04-26 2007-11-08 Idemitsu Kosan Co., Ltd. 芳香族アミン誘導体及びそれらを用いた有機エレクトロルミネッセンス素子
JP2012097091A (ja) * 2007-12-03 2012-05-24 Semiconductor Energy Lab Co Ltd カルバゾール誘導体、カルバゾール誘導体を用いた発光素子、照明装置、発光装置、および電子機器
JP5420310B2 (ja) * 2008-05-16 2014-02-19 株式会社半導体エネルギー研究所 トリアリールアミン誘導体、発光物質、発光素子、発光装置及び電子機器
WO2009145016A1 (ja) * 2008-05-29 2009-12-03 出光興産株式会社 芳香族アミン誘導体及びそれらを用いた有機エレクトロルミネッセンス素子
US20160043325A1 (en) * 2011-01-11 2016-02-11 Mitsubishi Chemical Corporation Composition for organic electroluminescent element, organic electroluminescent element, display and lighting
KR20150023657A (ko) * 2012-06-06 2015-03-05 메르크 파텐트 게엠베하 유기 전자 소자용 페난트렌 화합물
US20150295181A1 (en) * 2012-11-12 2015-10-15 Merck Patent Gmbh Materials for electronic devices
US20140197381A1 (en) * 2013-01-11 2014-07-17 Se-Hun Kim Organic light-emitting diode comprising amine-based compounds and pyrene-based compounds
WO2016032137A1 (ko) * 2014-08-29 2016-03-03 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR101530049B1 (ko) * 2014-10-24 2015-06-18 덕산네오룩스 주식회사 유기전기소자용 조성물을 이용한 디스플레이 장치 및 유기전기소자
WO2016190600A1 (ko) * 2015-05-27 2016-12-01 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20160149975A (ko) * 2015-06-17 2016-12-28 삼성디스플레이 주식회사 유기 전계 발광 소자용 재료 및 이를 포함하는 유기 전계 발광 소자
WO2017146466A1 (ko) * 2016-02-23 2017-08-31 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
US20170288147A1 (en) * 2016-03-30 2017-10-05 Samsung Display Co., Ltd. Organic light emitting device
KR20180044799A (ko) * 2016-10-21 2018-05-03 삼성디스플레이 주식회사 모노아민 화합물 및 이를 포함하는 유기 전계 발광 소자

Non-Patent Citations (18)

* Cited by examiner, † Cited by third party
Title
无: "CAS 1196694-40-2", 《STN REGISTRY》 *
无: "CAS 1233141-16-6", 《STN REGISTRY》 *
无: "CAS 1245939-64-3", 《STN REGISTRY》 *
无: "CAS 1253970-37-4", 《STN REGISTRY》 *
无: "CAS 1481692-54-9", 《STN REGISTRY》 *
无: "CAS 1481695-22-0", 《STN REGISTRY》 *
无: "CAS 2036269-25-5", 《STN REGISTRY》 *
无: "CAS 2055763-57-8", 《STN REGISTRY》 *
无: "CAS 2061992-86-5", 《STN REGISTRY》 *
无: "CAS 2061993-03-9", 《STN REGISTRY》 *
无: "CAS 2061993-04-0", 《STN REGISTRY》 *
无: "CAS 2061993-15-3", 《STN REGISTRY》 *
无: "CAS 2079057-28-4", 《STN REGISTRY》 *
无: "CAS 2165371-81-1", 《STN REGISTRY》 *
无: "CAS 2169955-67-1", 《STN REGISTRY》 *
无: "CAS 2179125-17-6", 《STN REGISTRY》 *
无: "CAS 656222-28-5", 《STN REGISTRY》 *
无: "CAS 792924-35-7", 《STN REGISTRY》 *

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111995530A (zh) * 2019-05-27 2020-11-27 东进世美肯株式会社 覆盖层用有机化合物及包含其的有机发光器件
CN112538060A (zh) * 2019-09-23 2021-03-23 东进世美肯株式会社 全新的覆盖层用有机化合物以及包含上述覆盖层用有机化合物的有机发光元件
CN112538060B (zh) * 2019-09-23 2024-10-29 东进世美肯株式会社 全新的覆盖层用有机化合物以及包含上述覆盖层用有机化合物的有机发光元件
US11930700B2 (en) 2019-12-30 2024-03-12 Shaanxi Lighte Optoelectronics Material Co., Ltd. Nitrogen-containing compound, electronic element, and electronic device
WO2021135542A1 (zh) * 2019-12-30 2021-07-08 陕西莱特光电材料股份有限公司 含氮化合物、电子元件和电子装置
CN114514220A (zh) * 2020-01-19 2022-05-17 广州华睿光电材料有限公司 有机电致发光器件和含稠环的芳胺类化合物
WO2021143246A1 (zh) * 2020-01-19 2021-07-22 广州华睿光电材料有限公司 有机电致发光器件和含稠环的芳胺类化合物
CN113745436B (zh) * 2020-05-29 2024-04-02 乐金显示有限公司 有机发光装置
CN113745436A (zh) * 2020-05-29 2021-12-03 乐金显示有限公司 有机发光装置
WO2022166623A1 (zh) * 2021-02-03 2022-08-11 烟台显华光电材料研究院有限公司 一种有机电致发光器件及包含该器件的显示装置
CN112952020A (zh) * 2021-02-03 2021-06-11 烟台显华光电材料研究院有限公司 一种有机电致发光器件及包含该器件的显示装置
CN112952020B (zh) * 2021-02-03 2024-06-18 烟台显华光电材料研究院有限公司 一种有机电致发光器件及包含该器件的显示装置
CN112952019B (zh) * 2021-02-03 2024-06-21 烟台显华光电材料研究院有限公司 一种有机电致发光器件及包含该器件的显示装置
CN112952019A (zh) * 2021-02-03 2021-06-11 烟台显华光电材料研究院有限公司 一种有机电致发光器件及包含该器件的显示装置
CN115260157A (zh) * 2021-04-29 2022-11-01 常州强力昱镭光电材料有限公司 立体环喹喔啉化合物、有机电致发光器件、显示装置及应用
CN115260157B (zh) * 2021-04-29 2023-09-29 常州强力昱镭光电材料有限公司 立体环喹喔啉化合物、有机电致发光器件、显示装置及应用
CN114685396A (zh) * 2022-04-02 2022-07-01 京东方科技集团股份有限公司 一种光提取材料、光提取层、发光器件和显示装置

Also Published As

Publication number Publication date
CN110577471B (zh) 2023-09-29
KR20190140233A (ko) 2019-12-19
US20190378981A1 (en) 2019-12-12
US11469378B2 (en) 2022-10-11

Similar Documents

Publication Publication Date Title
CN110577471B (zh) 电致发光化合物和包括该电致发光化合物的电致发光装置
KR102192692B1 (ko) 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR102087511B1 (ko) 플루오렌 유도체 및 이를 포함하는 유기 발광 소자
KR20180096458A (ko) 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR102032599B1 (ko) 아민 화합물 및 이를 포함하는 유기 발광 소자
KR102665302B1 (ko) 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20200022963A (ko) 유기발광 화합물 및 이를 포함하는 유기발광소자
KR102087487B1 (ko) 신규 화합물 및 이를 포함하는 유기 발광 소자
CN115175973A (zh) 有机发光化合物及包含其的有机发光器件
KR102316570B1 (ko) 유기발광 화합물 및 이를 포함하는 유기발광소자
KR102120917B1 (ko) 유기발광 화합물 및 이를 포함하는 유기발광소자
KR20190124620A (ko) 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR20240099130A (ko) 화합물 및 이를 포함하는 유기 발광 소자
KR102120916B1 (ko) 유기발광 화합물 및 이를 포함하는 유기전계발광소자
CN115380099A (zh) 有机发光化合物及包含其的有机发光器件
KR102232409B1 (ko) 화합물 및 이를 포함하는 유기 발광 소자
KR102438617B1 (ko) 유기발광 화합물 및 이를 포함하는 유기전계발광소자
CN111770920B (zh) 化合物及包含其的有机发光器件
KR102228753B1 (ko) 화합물 및 이를 포함하는 유기 발광 소자
CN111212829B (zh) 螺环化合物及包含其的有机发光装置
CN116724684A (zh) 有机化合物及包含其的有机发光器件
KR20210017428A (ko) 다환 화합물 및 이를 포함하는 유기 발광 소자
KR20200071277A (ko) 유기발광 화합물 및 이를 포함하는 유기발광소자
KR102449079B1 (ko) 유기발광 화합물 및 이를 포함하는 유기전계발광소자
KR102665301B1 (ko) 유기발광 화합물 및 이를 포함하는 유기전계발광소자

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant