[go: up one dir, main page]

WO2012169821A1 - Nouveaux composés pour une matière électronique organique et dispositif électroluminescent organique utilisant ces nouveaux composés - Google Patents

Nouveaux composés pour une matière électronique organique et dispositif électroluminescent organique utilisant ces nouveaux composés Download PDF

Info

Publication number
WO2012169821A1
WO2012169821A1 PCT/KR2012/004530 KR2012004530W WO2012169821A1 WO 2012169821 A1 WO2012169821 A1 WO 2012169821A1 KR 2012004530 W KR2012004530 W KR 2012004530W WO 2012169821 A1 WO2012169821 A1 WO 2012169821A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
unsubstituted
alkyl
aryl
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.)
Ceased
Application number
PCT/KR2012/004530
Other languages
English (en)
Inventor
Mi-Ja Lee
Young-Jun Cho
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.)
DuPont Specialty Materials Korea Ltd
DuPont Electronic Materials International LLC
Original Assignee
Rohm and Haas Electronic Materials Korea Ltd
Rohm and Haas Electronic Materials LLC
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 Rohm and Haas Electronic Materials Korea Ltd, Rohm and Haas Electronic Materials LLC filed Critical Rohm and Haas Electronic Materials Korea Ltd
Priority to JP2014514806A priority Critical patent/JP2014518900A/ja
Priority to CN201280036650.0A priority patent/CN103703003A/zh
Publication of WO2012169821A1 publication Critical patent/WO2012169821A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • C07D403/04—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 directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—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
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • 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
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
    • 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
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/40—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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—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
    • H10K85/6574—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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—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
    • 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
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/10—Transparent electrodes, e.g. using graphene
    • H10K2102/101—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO]
    • H10K2102/103—Transparent electrodes, e.g. using graphene comprising transparent conductive oxides [TCO] comprising indium oxides, e.g. ITO

Definitions

  • the present invention relates to novel compounds for organic electronic material and an organic electroluminescent device using the same.
  • An electroluminescent (EL) device is a self-light-emitting device which has advantages over other types of display devices in that it provides a wider viewing angle, a greater contrast ratio, and has a faster response time.
  • An organic EL device was first developed by Eastman Kodak, by using small molecules which are aromatic diamines, and aluminum complexes as a material for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C3’)iridium(acetylacetonate) ((acac)Ir(btp) 2 ), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ) and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red, green and blue materials, respectively.
  • phosphorescent materials including bis(2-(2’-benzothienyl)-pyridinato-N,C3’)iridium(acetylacetonate) ((acac)Ir(btp) 2 ), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ) and bis(4,6-difluorophenylpyridinato-N,C2)pic
  • CBP 4,4’-N,N’-dicarbazol-biphenyl
  • BCP bathocuproine
  • BAlq aluminum(III)bis(2-methyl-8-quinolinate)(4-phenylphenolate)
  • Pioneer (Japan) et al. developed a high performance organic EL device employing a derivative of BAlq as a host material.
  • WO 2006/049013 discloses compounds for organic electroluminescent materials having a condensed bicyclic group as a backbone structure. However, it does not disclose a fused carbazole compound substituted with a nitrogen-containing condensed bicyclic group substituted with an aromatic ring-fused heterocycloalkyl or cycloalkyl group.
  • the objective of the present invention is to provide a compound for organic electronic material which has an excellent structure imparting high luminous efficiency and a long operation lifetime to a device, and having proper color coordination; and an organic electroluminescent device having high efficiency and a long lifetime, using said compounds.
  • L 1 and L 2 each independently represent a single bond, a substituted or unsubstituted 3- to 30-membered heteroarylene group, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (C6-C30)cycloalkylene group;
  • X 1 represents CH or N
  • Y 1 to Y 3 each independently represent -O-, -S-, -CR 6 R 7 - or -NR 8 -, provided that Y 2 and Y 3 do not simultaneously exist;
  • R 1 to R 5 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted 5- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl group, -NR 11 R 12 , -SiR 13 R 14 R 15 , -SR 16 , -OR 17 , a cyano group, a nitro group, or a hydroxyl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, (C5-C30)alicycl
  • R 6 to R 8 and R 11 to R 17 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted 5- to 7-membered heterocycloalkyl group, or a substituted or unsubstituted (C3-C30)cycloalkyl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, (C5-C30)alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
  • a, b, c and e each independently represent an integer of 1 to 4; where a, b, c or e is an integer of 2 or more, each of R 1 , each of R 2 , each of R 3 or each of R 5 is the same or different;
  • d represents an integer of 1 to 3; where d is an integer of 2 or more, each of R 4 is the same or different; and
  • the compounds for organic electronic materials according to the present invention can manufacture an organic electroluminescent device which has high luminous efficiency and a long operation lifetime.
  • the compounds according to the present invention have high efficiency in transporting electrons, crystallization could be prevented when manufacturing a device. Further, the compounds have good layer formability and improve the current characteristic of the device. Therefore, they can produce an organic electroluminescent device having lowered driving voltages and enhanced power efficiency.
  • the present invention relates to a compound for organic electronic materials represented by the above formula 1 and an organic electroluminescent device comprising the compound.
  • (C1-C30)alkyl(ene) is meant to be a linear or branched alkyl(ene) having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert -butyl, etc., but are not limited thereto;
  • “(C2-C30) alkenyl(ene)” is meant to be a linear or branched alkenyl(ene) having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc., but are not limited thereto; “(C2-C30)alkynyl” is
  • substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent.
  • L 1 and L 2 each independently are preferably a single bond, a (C6-C12)arylene group substituted or unsubstituted with a (C1-C6)alkyl or an unsubstituted (C6-C30)cycloalkylene, more preferably a single bond, phenylene, biphenylene, dimethylphenylene or cyclohexylene.
  • Y 1 to Y 3 each independently represent -O-, -S-, -CR 6 R 7 - or -NR 8 -, wherein R 6 and R 8 each independently are preferably hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30-membered heteroaryl group; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, (C5-C30)alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur, more preferably a (C1-C6)alkyl group; a (C6-C20)aryl group substituted or unsubstituted with deuterium, halogen, (C1-C6)alkyl group, a (
  • R 1 to R 5 each independently are preferably hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, N-carbazolyl, -NR 11 R 12 or -SiR 13 R 14 R 15 ; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, (C5-C30)alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur, wherein R 11 to R 15 each independently are preferably a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a substituted or unsubstituted 3- to 30-membered hetero
  • R 1 to R 5 each independently are more preferably an unsubstituted (C6-C20)aryl group, an unsubstituted 5- to 21-membered heteroaryl group, -NR 11 R 12 or -SiR 13 R 14 R 15 ; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, (C5-C30)alicyclic or aromatic ring, even more preferably phenyl, carbazolyl, diphenylamino or methyldiphenylsilyl; or are linked to an adjacent substituent(s) to form a mono- or polycyclic, (C5-C30)alicyclic or aromatic ring.
  • the representative compounds of the present invention include the following compounds, but are not limited thereto:
  • the compounds for organic electronic materials according to the present invention can be prepared according to the following reaction scheme.
  • R 1 to R 5 , Y 1 to Y 3 , X 1 , L 1 , L 2 , a, b, c, d and e are as defined in formula 1 above, and X represents a halogen.
  • the present invention provides an organic electroluminescent device comprising the compound of formula 1.
  • Said organic electroluminescent device comprises a first electrode, a second electrode, and at least one organic layer between said first and second electrodes.
  • Said organic layer comprises at least one compound of formula 1 according to the present invention.
  • said organic layer comprises a light-emitting layer in which the compound of formula 1 is comprised as a host material.
  • a phosphorescent dopant which is used for an organic electroluminescent device together with the host material according to the present invention, may be selected from compounds represented by the following formula 2:
  • M 1 is selected from the group consisting of Ir, Pt, Pd and Os;
  • L 101 , L 102 and L 103 are each independently selected from the following structures:
  • R 201 to R 203 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a (C6-C30)aryl group unsubstituted or substituted with (C1-C30)alkyl group(s), or a halogen;
  • R 204 to R 219 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, SF 5 , a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)aryl
  • R 220 to R 223 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), or a (C6-C30)aryl group unsubstituted or substituted with (C1-C30)alkyl group(s);
  • R 224 and R 225 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a halogen, or R 224 and R 225 may be linked to each other via a (C3-C12)alkylene group or (C3-C12)alkenylene group with or without a fused ring, to form a mono- or polycyclic, alicyclic or aromatic ring;
  • R 226 represents a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- or 30-membered heteroaryl group or a halogen;
  • R 227 to R 229 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group or a halogen;
  • R 231 to R 242 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a (C1-C30)alkoxy group, a halogen, a substituted or unsubstituted (C6-C30)aryl group, a cyano group, or a substituted or unsubstituted (C5-C30)cycloalkyl group, or each of R 231 to R 242 may be linked to an adjacent substituent via (C2-C30)alkylene group or (C2-C30)alkenylene group to form a spiro ring or a fused ring or may be linked to R 207 or R 208 via a (C2-C30)alkylene group or (C2-C30)alkenylene group to form a saturated or unsaturated fused ring.
  • the dopants of formula 2 include the following, but are not limited thereto:
  • the organic electroluminescent device according to the present invention may further comprise, in addition to the compounds represented by formula 1, at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
  • the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal.
  • the organic layer may comprise a light-emitting layer and a charge generating layer.
  • the organic electroluminescent device may emit white light by further comprising at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound, besides the compound according to the present invention.
  • a surface layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s).
  • a chalcogenide(includes oxides) layer of silicon or aluminum is placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or metal oxide layer is placed on a cathode surface of an electroluminescent medium layer.
  • Such a surface layer provides operation stability for the organic electroluminescent device.
  • said chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.; said metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and said metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a mixed region of an electron transport compound and an reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
  • the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to an electroluminescent medium.
  • the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
  • the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • a reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting white light.
  • Example 1 Production of an OLED device using the compound according to the present invention
  • OLED device was produced using the compound according to the present invention.
  • a transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and then was stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • N 1 ,N 1' -([1,1’-biphenyl]-4,4’-diyl)bis(N 1 -(naphthalen-1-yl)-N 4 ,N 4 -diphenylbenzene-1,4-diamine) was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a hole injection layer having a thickness of 60 nm on the ITO substrate.
  • N,N’-di(4-biphenyl)-N,N’-di(4-biphenyl)-4,4’-diaminobiphenyl was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • compound C-5 was introduced into one cell of the vacuum vapor depositing apparatus, as a host material
  • compound D-11 was introduced into another cell as a dopant.
  • the two materials were evaporated at different rates and were deposited in a doping amount of 4 wt% to form a light-emitting layer having a thickness of 30 nm on the hole transport layer.
  • the produced OLED device showed red emission having a luminance of 1,135 cd/m 2 and a current density of 15.2 mA/cm 2 at a driving voltage of 5.1 V. Further, the minimum time taken to be reduced to 90 % of the luminance at a luminance of 5,000 nit was 70 hours.
  • Example 2 Production of an OLED device using the compound according to the present invention
  • An OLED device was produced in the same manner as in Example 1, except for using compound C-11 as a host material, and compound D-11 as a dopant.
  • the produced OLED device showed red emission having a luminance of 1,010 cd/m 2 and a current density of 12.2 mA/cm 2 at a driving voltage of 4.9 V. Further, the minimum time taken to be reduced to 90 % of the luminance at a luminance of 5,000 nit was 80 hours.
  • Example 3 Production of an OLED device using the compound according to the present invention
  • An OLED device was produced in the same manner as in Example 1, except for using compound C-34 as a host material, and compound D-7 as a dopant.
  • the produced OLED device showed red emission having a luminance of 1,090 cd/m 2 and a current density of 7.3 mA/cm 2 at a driving voltage of 6.0 V. Further, the minimum time taken to be reduced to 90 % of the luminance at a luminance of 5,000 nit was 140 hours.
  • Example 4 Production of an OLED device using the compound according to the present invention
  • An OLED device was produced in the same manner as in Example 1, except for using compound C-80 as a host material, and compound D-7 as a dopant.
  • the produced OLED device showed red emission having a luminance of 1,180 cd/m 2 and a current density of 7.9 mA/cm 2 at a driving voltage of 5.8 V. Further, the minimum time taken to be reduced to 90 % of the luminance at a luminance of 5,000 nit was 100 hours.
  • Example 5 Production of an OLED device using the compound according to the present invention
  • An OLED device was produced in the same manner as in Example 1, except for using compound C-103 as a host material, and compound D-6 as a dopant.
  • the produced OLED device showed red emission having a luminance of 1,100 cd/m 2 and a current density of 16.4 mA/cm 2 at a driving voltage of 5.1 V. Further, the minimum time taken to be reduced to 90 % of the luminance at a luminance of 5,000 nit was 90 hours.
  • Comparative Example 1 Production of an OLED device using conventional electroluminescent compounds
  • An OLED device was produced in the same manner as that of Example 1, except that a light-emitting layer having a thickness of 30 nm was deposited on the hole transport layer by using 4,4’-N,N’-dicarbazol-biphenyl (CBP) as a host material and compound D-11 as a dopant and that a hole blocking layer having a thickness of 10 nm was deposited by using aluminum(III) bis(2-methyl-8-quinolinato)-4-phenylphenolate.
  • CBP 4,4’-N,N’-dicarbazol-biphenyl
  • the produced OLED device showed red emission having a luminance of 1,000 cd/m 2 and a current density of 20.0 mA/cm 2 at a driving voltage of 8.2V. Further, the minimum time taken to be reduced to 90 % of the luminance at a luminance of 5,000nit was 10 hours.
  • the compounds for organic electronic material of the present invention have superior luminous characteristics than the conventional materials.
  • a device using the compounds according to the present invention as a host material not only has excellent luminous characteristics, but also induces an increase in power efficiency by reducing a driving voltage, and thus can improve power consumption.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique le contenant. Etant donné que les composés selon la présente invention ont un rendement élevé en transport d'électrons, une cristallisation a pu être empêchée lors de la fabrication d'un dispositif. En outre, les composés présentent une bonne aptitude au façonnage de couche et améliorent les caractéristiques de courant du dispositif. En conséquence, ils peuvent produire un dispositif électroluminescent organique ayant des tensions de commande diminuées et un rendement énergétique amélioré.
PCT/KR2012/004530 2011-06-09 2012-06-08 Nouveaux composés pour une matière électronique organique et dispositif électroluminescent organique utilisant ces nouveaux composés Ceased WO2012169821A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2014514806A JP2014518900A (ja) 2011-06-09 2012-06-08 有機電子材料用の新規な化合物および同化合物を使用した有機電界発光素子
CN201280036650.0A CN103703003A (zh) 2011-06-09 2012-06-08 用于有机电子材料的新化合物以及使用该化合物的有机电致发光器件

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020110055657A KR20120136618A (ko) 2011-06-09 2011-06-09 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자
KR10-2011-0055657 2011-06-09

Publications (1)

Publication Number Publication Date
WO2012169821A1 true WO2012169821A1 (fr) 2012-12-13

Family

ID=47296260

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2012/004530 Ceased WO2012169821A1 (fr) 2011-06-09 2012-06-08 Nouveaux composés pour une matière électronique organique et dispositif électroluminescent organique utilisant ces nouveaux composés

Country Status (5)

Country Link
JP (1) JP2014518900A (fr)
KR (1) KR20120136618A (fr)
CN (1) CN103703003A (fr)
TW (1) TW201305313A (fr)
WO (1) WO2012169821A1 (fr)

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013040105A (ja) * 2011-07-15 2013-02-28 Idemitsu Kosan Co Ltd 含窒素芳香族複素環誘導体およびそれを用いた有機エレクトロルミネッセンス素子
WO2013088973A1 (fr) * 2011-12-15 2013-06-20 新日鉄住金化学株式会社 Élément électroluminescent organique
WO2014050588A1 (fr) * 2012-09-28 2014-04-03 新日鉄住金化学株式会社 Matériau d'élément électroluminescent organique et élément électroluminescent organique l'utilisant
WO2014088300A1 (fr) * 2012-12-04 2014-06-12 Rohm And Haas Electronic Materials Korea Ltd. Composés à électroluminescence organique et dispositif à électroluminescence organique les comprenant
WO2014092478A1 (fr) * 2012-12-13 2014-06-19 주식회사 두산 Composé organique et dispositif électroluminescent organique le comprenant
WO2014098447A1 (fr) * 2012-12-17 2014-06-26 주식회사 두산 Composé organique et élément électroluminescent organique le comprenant
JP2014196251A (ja) * 2013-03-29 2014-10-16 出光興産株式会社 ヘテロアレーン誘導体、有機エレクトロルミネッセンス素子用材料、及び有機エレクトロルミネッセンス素子
WO2014199943A1 (fr) * 2013-06-14 2014-12-18 保土谷化学工業株式会社 Dérivé dicarbazole et élément électroluminescent organique
WO2015046982A3 (fr) * 2013-09-30 2015-05-07 주식회사 두산 Composé organique et élément électroluminescent organique le contenant
KR20150070617A (ko) * 2013-12-17 2015-06-25 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2015170930A1 (fr) * 2014-05-08 2015-11-12 Rohm And Haas Electronic Materials Korea Ltd. Matériau de transport d'électrons et dispositif électroluminescent organique comprenant celui-ci
KR101571592B1 (ko) 2012-12-13 2015-11-25 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2016010380A1 (fr) 2014-07-17 2016-01-21 Rohm And Haas Electronic Materials Korea Ltd. Matériau de transport d'électrons et dispositif organique électroluminescent le comportant
WO2016018076A1 (fr) * 2014-07-29 2016-02-04 Rohm And Haas Electronic Materials Korea Ltd. Matériau tampon d'électrons et dispositif électroluminescent organique
WO2016048109A1 (fr) * 2014-09-26 2016-03-31 Rohm And Haas Electronic Materials Korea Ltd. Composé organique électroluminescent, et matériau organique électroluminescent et dispositif organique électroluminescent le comprenant
KR101612154B1 (ko) 2012-12-13 2016-04-14 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2016198144A1 (fr) 2015-06-10 2016-12-15 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
JP2017522732A (ja) * 2014-07-17 2017-08-10 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 電子輸送物質およびそれを含む有機エレクトロルミネセント素子
CN108003165A (zh) * 2017-12-21 2018-05-08 河南省科学院化学研究所有限公司 一种5,11-二氢-5-苯基吲哚并[3,2-b]咔唑的合成方法
EP3401318A1 (fr) * 2017-05-11 2018-11-14 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
CN111557122A (zh) * 2018-01-25 2020-08-18 默克专利有限公司 用于有机电致发光器件的材料
US10886474B2 (en) 2014-09-26 2021-01-05 Rohm And Haas Electronic Materials Korea Ltd Organic electroluminescent compound, and organic electroluminescent material and organic electroluminescent device comprising the same
CN113248522A (zh) * 2021-04-07 2021-08-13 浙江华显光电科技有限公司 一种有机化合物及使用该化合物的有机发光器件
US11201296B2 (en) 2015-07-29 2021-12-14 Merck Patent Gmbh Compounds having fluorene structures
US11925113B2 (en) 2018-04-24 2024-03-05 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same
US12459946B2 (en) * 2017-10-05 2025-11-04 Universal Display Corporation Organic host materials for electroluminescent devices

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20130025268A (ko) * 2011-09-01 2013-03-11 롬엔드하스전자재료코리아유한회사 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자
KR101601357B1 (ko) * 2012-12-24 2016-03-08 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
US9660200B2 (en) 2013-07-01 2017-05-23 Samsung Display Co., Ltd. Organic light-emitting device
KR101718887B1 (ko) 2013-07-01 2017-04-05 삼성디스플레이 주식회사 유기 발광 소자
CN104211634A (zh) * 2014-07-23 2014-12-17 常州创索新材料科技有限公司 一种2-溴咔唑的合成方法
WO2016119992A1 (fr) * 2015-01-30 2016-08-04 Merck Patent Gmbh Matières pour dispositifs électroniques
CN110392682B (zh) * 2017-03-28 2022-03-15 东丽株式会社 化合物、含有该化合物的电子器件、有机薄膜发光元件、显示装置及照明装置
WO2019212290A1 (fr) * 2018-05-04 2019-11-07 덕산네오룩스 주식회사 Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé
CN111995564B (zh) 2019-12-31 2021-11-12 陕西莱特光电材料股份有限公司 有机化合物、电子元件和电子装置
CN111978241B (zh) * 2020-03-27 2022-06-14 陕西莱特光电材料股份有限公司 有机化合物、电子元件和电子装置
CN120590317A (zh) * 2025-08-07 2025-09-05 山东浩华新材料科技有限公司 一种2-溴-9-苯基-9h-咔唑的制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090091240A1 (en) * 2004-11-04 2009-04-09 Idemitsu Kosan Co., Ltd. Compound containing fused ring and organic electroluminescent element employing the same
WO2012050347A1 (fr) * 2010-10-13 2012-04-19 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés pour matériau électronique organique et dispositif électroluminescent organique les utilisant

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8221905B2 (en) * 2007-12-28 2012-07-17 Universal Display Corporation Carbazole-containing materials in phosphorescent light emitting diodes
CN102070632B (zh) * 2009-11-20 2013-09-11 中国科学院理化技术研究所 吡啶并咪唑衍生物及其在有机电致发光器件中的应用
KR101531904B1 (ko) * 2010-10-13 2015-06-29 롬엔드하스전자재료코리아유한회사 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자
KR20120052879A (ko) * 2010-11-16 2012-05-24 롬엔드하스전자재료코리아유한회사 신규한 유기 전자재료용 화합물 및 이를 채용하고 있는 유기 전계 발광 소자

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090091240A1 (en) * 2004-11-04 2009-04-09 Idemitsu Kosan Co., Ltd. Compound containing fused ring and organic electroluminescent element employing the same
WO2012050347A1 (fr) * 2010-10-13 2012-04-19 Rohm And Haas Electronic Materials Korea Ltd. Nouveaux composés pour matériau électronique organique et dispositif électroluminescent organique les utilisant

Cited By (40)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12063851B2 (en) 2011-07-15 2024-08-13 Idemitsu Kosan Co., Ltd. Nitrogenated aromatic heterocyclic derivative and organic electroluminescent element using same
JP2013040105A (ja) * 2011-07-15 2013-02-28 Idemitsu Kosan Co Ltd 含窒素芳香族複素環誘導体およびそれを用いた有機エレクトロルミネッセンス素子
US10043977B2 (en) 2011-07-15 2018-08-07 Idemitsu Kosan Co., Ltd. Nitrogenated aromatic heterocyclic derivative, and organic electroluminescent element using same
WO2013088973A1 (fr) * 2011-12-15 2013-06-20 新日鉄住金化学株式会社 Élément électroluminescent organique
JPWO2013088973A1 (ja) * 2011-12-15 2015-04-27 新日鉄住金化学株式会社 有機電界発光素子
WO2014050588A1 (fr) * 2012-09-28 2014-04-03 新日鉄住金化学株式会社 Matériau d'élément électroluminescent organique et élément électroluminescent organique l'utilisant
JPWO2014050588A1 (ja) * 2012-09-28 2016-08-22 新日鉄住金化学株式会社 有機電界発光素子用材料及びこれを用いた有機電界発光素子
WO2014088300A1 (fr) * 2012-12-04 2014-06-12 Rohm And Haas Electronic Materials Korea Ltd. Composés à électroluminescence organique et dispositif à électroluminescence organique les comprenant
KR101571592B1 (ko) 2012-12-13 2015-11-25 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2014092478A1 (fr) * 2012-12-13 2014-06-19 주식회사 두산 Composé organique et dispositif électroluminescent organique le comprenant
KR101612154B1 (ko) 2012-12-13 2016-04-14 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR101577101B1 (ko) * 2012-12-13 2015-12-14 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR101601356B1 (ko) * 2012-12-17 2016-03-09 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2014098447A1 (fr) * 2012-12-17 2014-06-26 주식회사 두산 Composé organique et élément électroluminescent organique le comprenant
KR20140079595A (ko) * 2012-12-17 2014-06-27 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
JP2014196251A (ja) * 2013-03-29 2014-10-16 出光興産株式会社 ヘテロアレーン誘導体、有機エレクトロルミネッセンス素子用材料、及び有機エレクトロルミネッセンス素子
CN105452255A (zh) * 2013-06-14 2016-03-30 保土谷化学工业株式会社 二咔唑衍生物和有机电致发光器件
WO2014199943A1 (fr) * 2013-06-14 2014-12-18 保土谷化学工業株式会社 Dérivé dicarbazole et élément électroluminescent organique
JPWO2014199943A1 (ja) * 2013-06-14 2017-02-23 保土谷化学工業株式会社 ジカルバゾール誘導体及び有機エレクトロルミネッセンス素子
WO2015046982A3 (fr) * 2013-09-30 2015-05-07 주식회사 두산 Composé organique et élément électroluminescent organique le contenant
KR20150070617A (ko) * 2013-12-17 2015-06-25 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR101667447B1 (ko) 2013-12-17 2016-10-18 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
WO2015093818A3 (fr) * 2013-12-17 2015-08-13 주식회사 두산 Composé organique et dispositif électroluminescent organique comprenant un tel composé
WO2015170930A1 (fr) * 2014-05-08 2015-11-12 Rohm And Haas Electronic Materials Korea Ltd. Matériau de transport d'électrons et dispositif électroluminescent organique comprenant celui-ci
WO2016010380A1 (fr) 2014-07-17 2016-01-21 Rohm And Haas Electronic Materials Korea Ltd. Matériau de transport d'électrons et dispositif organique électroluminescent le comportant
JP2017522732A (ja) * 2014-07-17 2017-08-10 ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド 電子輸送物質およびそれを含む有機エレクトロルミネセント素子
WO2016018076A1 (fr) * 2014-07-29 2016-02-04 Rohm And Haas Electronic Materials Korea Ltd. Matériau tampon d'électrons et dispositif électroluminescent organique
WO2016048109A1 (fr) * 2014-09-26 2016-03-31 Rohm And Haas Electronic Materials Korea Ltd. Composé organique électroluminescent, et matériau organique électroluminescent et dispositif organique électroluminescent le comprenant
US10886474B2 (en) 2014-09-26 2021-01-05 Rohm And Haas Electronic Materials Korea Ltd Organic electroluminescent compound, and organic electroluminescent material and organic electroluminescent device comprising the same
WO2016198144A1 (fr) 2015-06-10 2016-12-15 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques
US11201296B2 (en) 2015-07-29 2021-12-14 Merck Patent Gmbh Compounds having fluorene structures
EP3401318A1 (fr) * 2017-05-11 2018-11-14 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
US20180331304A1 (en) * 2017-05-11 2018-11-15 Universal Display Corporation Organic electroluminescent materials and devices
US10944060B2 (en) * 2017-05-11 2021-03-09 Universal Display Corporation Organic electroluminescent materials and devices
EP4141010A1 (fr) * 2017-05-11 2023-03-01 Universal Display Corporation Matériaux électroluminescents organiques et dispositifs
US12459946B2 (en) * 2017-10-05 2025-11-04 Universal Display Corporation Organic host materials for electroluminescent devices
CN108003165A (zh) * 2017-12-21 2018-05-08 河南省科学院化学研究所有限公司 一种5,11-二氢-5-苯基吲哚并[3,2-b]咔唑的合成方法
CN111557122A (zh) * 2018-01-25 2020-08-18 默克专利有限公司 用于有机电致发光器件的材料
US11925113B2 (en) 2018-04-24 2024-03-05 Lg Chem, Ltd. Heterocyclic compound and organic light emitting device comprising the same
CN113248522A (zh) * 2021-04-07 2021-08-13 浙江华显光电科技有限公司 一种有机化合物及使用该化合物的有机发光器件

Also Published As

Publication number Publication date
KR20120136618A (ko) 2012-12-20
CN103703003A (zh) 2014-04-02
TW201305313A (zh) 2013-02-01
JP2014518900A (ja) 2014-08-07

Similar Documents

Publication Publication Date Title
WO2012169821A1 (fr) Nouveaux composés pour une matière électronique organique et dispositif électroluminescent organique utilisant ces nouveaux composés
WO2012050371A1 (fr) Nouveaux composés pour matériau électronique organique et dispositif électroluminescent organique les utilisant
WO2013012297A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
WO2013085243A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique utilisant ceux-ci
WO2012165832A1 (fr) Nouveaux composés pour une matière électronique organique et dispositif électroluminescent organique les utilisant
EP2683712A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique utilisant lesdits composés
WO2012165844A1 (fr) Composés inédits pour matériaux électroniques organiques et dispositif électroluminescent organique les utilisant
WO2013081416A1 (fr) Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent utilisant lesdits composés
WO2013157886A1 (fr) Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent les comprenant
WO2013073896A1 (fr) Nouveaux composés organiques électroluminescents et dispositif organique électroluminescent utilisant lesdits composés
WO2014042420A1 (fr) Nouveau composé à électroluminescence organique et dispositif à électroluminescence organique le comprenant
WO2014030921A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique contenant ceux-ci
EP2828264A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les contenant
WO2013180478A1 (fr) Nouveaux composés à électroluminescence organique et dispositif à électroluminescence organique les contenant
WO2012134124A1 (fr) Nouveaux composés pour matériau électronique organique et dispositif électroluminescent organique utilisant un tel matériau
EP2697216A1 (fr) Nouveau composé pour matériau électronique organique et dispositif électroluminescent organique l'utilisant
WO2014061963A1 (fr) Composés à électroluminescence organique et dispositif à électroluminescence organique les comprenant
WO2015084114A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
WO2012150826A1 (fr) Nouveaux composés organiques électroluminescents et dispositif électroluminescent organique les utilisant
WO2015012618A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé
WO2014061991A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique en contenant
WO2014171779A1 (fr) Composés électroluminescents organiques et dispositif électroluminescent organique les comprenant
WO2012050347A1 (fr) Nouveaux composés pour matériau électronique organique et dispositif électroluminescent organique les utilisant
WO2013032278A1 (fr) Nouveaux composés électroluminescents organiques et dispositif électroluminescent organique les utilisant
WO2016006925A1 (fr) Composé électroluminescent organique et dispositif électroluminescent organique comprenant ce composé

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 12797373

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2014514806

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 12797373

Country of ref document: EP

Kind code of ref document: A1