WO2015056965A1 - Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique associé - Google Patents

Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique associé Download PDF

Info

Publication number
WO2015056965A1
WO2015056965A1 PCT/KR2014/009649 KR2014009649W WO2015056965A1 WO 2015056965 A1 WO2015056965 A1 WO 2015056965A1 KR 2014009649 W KR2014009649 W KR 2014009649W WO 2015056965 A1 WO2015056965 A1 WO 2015056965A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
organic
layer
compound
present
Prior art date
Application number
PCT/KR2014/009649
Other languages
English (en)
Korean (ko)
Inventor
박정환
이선희
김원삼
변지훈
정화순
권재택
Original Assignee
덕산네오룩스 주식회사
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 덕산네오룩스 주식회사 filed Critical 덕산네오룩스 주식회사
Publication of WO2015056965A1 publication Critical patent/WO2015056965A1/fr

Links

Images

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
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • 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
    • C07D403/02—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
    • C07D403/12—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 chain containing hetero atoms as chain links
    • 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
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/85—Arrangements for extracting light from the devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero 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
    • 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
    • C09K2211/1018—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
    • C09K2211/1044—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
    • C09K2211/1092—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
    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electric device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
  • the material used as the organic material layer in the organic electric element may be classified into a light emitting material and a charge transport material such as a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
  • Efficiency, lifespan, and driving voltage are related to each other, and as efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic materials due to Joule heating generated during driving decreases. It shows a tendency to increase the life.
  • a light emitting auxiliary layer must exist between the hole transport layer and the light emitting layer, and different light emission auxiliary according to each light emitting layer (R, G, B) is required. It is time to develop the floor.
  • electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer to generate excitons by recombination.
  • the material used in the hole transport layer has a low TMO value because it has to have a low HOMO value, which causes the exciton generated in the light emitting layer to pass to the hole transport layer, resulting in charge unbalance in the light emitting layer. This causes light emission at the hole transport layer interface.
  • the OLED device is mainly formed by a deposition method, which requires development of a material that can withstand a long time during deposition, that is, a material having strong heat resistance.
  • the materials constituting the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a light emitting auxiliary layer material, etc.
  • a hole injection material such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, a light emitting auxiliary layer material, etc.
  • the material should be preceded, but development of a stable and efficient organic material layer for an organic electric device has not been made yet. Therefore, the development of new materials continues to be required, and in particular, the development of materials for the light emitting auxiliary layer and the hole transport layer is urgently required.
  • An object of the present invention is to provide a compound capable of improving high luminous efficiency, low driving voltage, high heat resistance, color purity and lifetime of an element, an organic electric element using the same, and an electronic device thereof.
  • the present invention provides a compound represented by the following formula.
  • the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device thereof.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to the present invention.
  • halo or halogen as used herein is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise indicated.
  • alkyl or “alkyl group” has a single bond of 1 to 60 carbon atoms, unless otherwise indicated, and is a straight chain alkyl group, branched chain alkyl group, cycloalkyl (alicyclic) group, alkyl-substituted cyclo Radicals of saturated aliphatic functional groups, including alkyl groups, cycloalkyl-substituted alkyl groups.
  • heteroalkyl group means that at least one of the carbon atoms constituting the alkyl group has been replaced with a heteroatom.
  • alkenyl group or “alkynyl group”, unless stated otherwise, has a double or triple bond of 2 to 60 carbon atoms, and includes a straight or branched chain group, and is not limited thereto. It is not.
  • cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
  • alkoxyl group means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, and is limited herein. It is not.
  • alkenoxyl group means an alkenyl group to which an oxygen radical is attached, and unless otherwise stated, it is 2 to 60 It has carbon number of, It is not limited to this.
  • aryloxyl group or “aryloxy group” means an aryl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 6 to 60, but is not limited thereto.
  • aryl group and “arylene group” have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
  • an aryl group or an arylene group means an aromatic of a single ring or multiple rings, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction.
  • the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.
  • aryl or "ar” means a radical substituted with an aryl group.
  • an arylalkyl group is an alkyl group substituted with an aryl group
  • an arylalkenyl group is an alkenyl group substituted with an aryl group
  • the radical substituted with an aryl group has the carbon number described herein.
  • an arylalkoxy group means an alkoxy group substituted with an aryl group
  • an alkoxylcarbonyl group means a carbonyl group substituted with an alkoxyl group
  • an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group.
  • the arylcarbonyl group is a carbonyl group substituted with an aryl group.
  • heteroalkyl means an alkyl including one or more heteroatoms unless otherwise indicated.
  • heteroaryl group or “heteroarylene group” means an aryl group or arylene group having 2 to 60 carbon atoms, each containing one or more heteroatoms, unless otherwise specified. It may include at least one of a single ring and multiple rings, and may be formed by combining adjacent functional groups.
  • heterocyclic group includes one or more heteroatoms, unless otherwise indicated, and has from 2 to 60 carbon atoms, and includes at least one of single and multiple rings, heteroaliphatic rings and hetero Aromatic rings. Adjacent functional groups may be formed in combination.
  • heteroatom refers to N, O, S, P or Si unless otherwise stated.
  • Heterocyclic groups may also include rings comprising SO 2 in place of the carbon forming the ring.
  • a “heterocyclic group” includes the following compounds.
  • aliphatic as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms
  • aliphatic ring means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
  • ring refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a hetero ring having 2 to 60 carbon atoms, or a combination thereof. Saturated or unsaturated rings.
  • heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.
  • carbonyl used in the present invention is represented by -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. Cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
  • ether as used herein is represented by -RO-R ', wherein R or R' are each independently of each other hydrogen, an alkyl group having 1 to 20 carbon atoms, It is an aryl group, a C3-C30 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, or a combination thereof.
  • substituted in the term “substituted or unsubstituted” as used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, C 1 ⁇ C 20 alkoxyl group, C 1 ⁇ C 20 alkylamine group, C 1 ⁇ C 20 alkylthiophene group, C 6 ⁇ C 20 arylthiophene group, C 2 ⁇ C 20 alkenyl group, C 2 ⁇ C 20 alkynyl, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 20 aryl group, of a C 6 ⁇ C 20 substituted by deuterium aryl group, a C 8 ⁇ C 20 aryl alkenyl group, a silane group, a boron Group, germanium group, and C 2 ⁇ C 20 It is meant to be substituted with one or more substituents selected from the group consist
  • the substituent R 1 when a is an integer of 0, the substituent R 1 is absent, when a is an integer of 1, one substituent R 1 is bonded to any one of carbons forming the benzene ring, and a is an integer of 2 or 3 are each bonded as follows, where R 1 may be the same or different from each other, and when a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bonded to the carbon forming the benzene ring Is omitted.
  • FIG. 1 is an exemplary view of an organic electric device according to an embodiment of the present invention.
  • the organic electric device 100 includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110.
  • the first electrode 120 may be an anode (anode)
  • the second electrode 180 may be a cathode (cathode)
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence. At this time, the remaining layers except for the light emitting layer 150 may not be formed.
  • the hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.
  • the organic electric device according to the present invention may further include a protective layer or a light efficiency improving layer (Capping layer) formed on one surface of the at least one surface of the first electrode and the second electrode opposite to the organic material layer.
  • a protective layer or a light efficiency improving layer Capping layer
  • the compound according to the present invention applied to the organic material layer of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, the host of the dopant or light efficiency improvement layer of the light emitting layer 150 Can be used as a material.
  • the organic electroluminescent device may be manufactured using a PVD method.
  • the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer are formed thereon.
  • the organic material layer including the 160 and the electron injection layer 170 it can be prepared by depositing a material that can be used as the cathode 180 thereon.
  • the organic material layer is a solution or solvent process (e.g., spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blading) using various polymer materials. It can be produced in fewer layers by methods such as ding process, screen printing process, or thermal transfer method. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.
  • the organic electric element according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • WOLED White Organic Light Emitting Device
  • Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented. Representatively, a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting parts are mutually planarized, and a stacking method in which R, G, and B light emitting layers are stacked up and down. And a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light therefrom. May also be applied to these WOLEDs.
  • CCM color conversion material
  • the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device.
  • OLED organic electroluminescent device
  • OPC organic photoconductor
  • organic TFT organic transistor
  • Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device.
  • the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
  • the compound according to one aspect of the present invention is represented by the following formula (1).
  • Ar 1 and Ar 2 are each independently a C 6 ⁇ C 60 aryl group; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; C 1 ⁇ C 50 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 -C 30 alkoxyl group; C 6 -C 30 aryloxy group; And -L'-N (R a ) (R b );
  • R 1 to R 14 are i) independently of each other hydrogen; heavy hydrogen; halogen; C 6 ⁇ C 60 Aryl group; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C 3 ⁇ C 60 i of the aliphatic ring and C 6 ⁇ C 60; C 1 ⁇ C 50 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 -C 30 alkoxyl group; C 6 -C 30 aryloxy group; And -L'-N (R a ) (R b ); or ii) neighboring groups may combine with each other to form a ring.
  • neighboring groups combine with each other to form a ring
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 9 and R 10 , R 10 and R 11 and R 13 and R 14 are bonded to each other to form a ring
  • the ring is C 3 ⁇ C 60 aliphatic ring, C 6 ⁇ C 60 aromatic ring, It refers to a fused ring consisting of a C 2 ⁇ C 60 heterocycle or a combination thereof, and includes a saturated or unsaturated ring.
  • L ′ is a single bond independently of each other; C 6 ⁇ C 60 arylene group; Fluorenylene groups; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; And C 2 ⁇ C 60 It is selected from the group consisting of; heterocyclic group,
  • R a and R b are each independently a C 6 ⁇ C 60 aryl group; Fluorenyl group; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; And a C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si, and P.
  • aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group, arylene group, fluorenylene group are each deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; -L'-N (R a ) (R b ); C 1 ⁇ C 20 of the import alkylthio; C 1 -C 20 alkoxyl group; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; Of C 6 ⁇ C 20 Aryl group; C 6 ⁇ C 20 aryl group substituted with deuterium; Fluorenyl group; C 2 ⁇ C 20 heterocyclic group; C 3 -C 20 cycloalkyl group; It may be further substituted with one or more
  • Chemical Formula 1 may be represented by the following Chemical Formulas 2 to 4.
  • R 1 to R 14 , L ', R a and R b are the same as defined in Formula 1,
  • Ar 3 to Ar 5 are each independently a C 6 ⁇ C 60 aryl group; Fluorenyl group; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; Fused ring group of an aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; C 1 ⁇ C 50 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; C 1 -C 30 alkoxyl group; And C 6 ⁇ C 30 An aryloxy group; It is selected from the group consisting of.
  • the compound represented by Formula 1 may be any one of the following compounds.
  • the present invention comprises a first electrode; Second electrode; And an organic material layer disposed between the first electrode and the second electrode, wherein the organic material layer provides an organic electric device including the compound represented by Chemical Formula 1.
  • the present invention provides an organic electric device comprising one of the compounds represented by Formula 2 to Formula 4 in the organic material layer. More specifically, the present invention provides an organic electric device comprising a compound represented by the respective formula in the organic material layer.
  • the present invention provides an organic electroluminescent device comprising at least a hole transport layer in the organic material layer, the hole transport layer comprises the compound.
  • the present invention provides an organic electroluminescent device comprising at least a light emitting auxiliary layer in the organic material layer, wherein the light emitting auxiliary layer comprises the compound.
  • the present invention provides an organic electroluminescent device comprising at least a light emitting layer in the organic material layer, the compound is used as a host material of the light emitting layer.
  • the present invention is an optical efficiency improvement layer formed on at least one side of the one side of the first electrode opposite to the organic material layer or one side of the second electrode opposite to the organic material layer It provides an organic electric element further comprising.
  • the present invention provides an organic electroluminescent device is formed by any one of the organic layer is spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process and roll-to-roll process do.
  • the present invention is a display device including an organic electric element comprising the organic material layer; And a controller for driving the display device.
  • the organic electroluminescent device according to the present invention is at least one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), and a device for monochrome or white illumination It can be one.
  • OLED organic electroluminescent device
  • OPC organic photoconductor
  • organic TFT organic transistor
  • a device for monochrome or white illumination It can be one.
  • Compound represented by Formula 1 according to the present invention is prepared by reacting Sub 1 and Sub 2 as shown in Scheme 1, but is not limited thereto.
  • Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2, but is not limited thereto.
  • Sub 1 examples are as follows, but are not limited thereto, and their FD-MS are shown in Table 1 below.
  • Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 3, but is not limited thereto.
  • 1,4-diamine hereinafter, abbreviated as "2-TNATA” was vacuum deposited to a thickness of 60 nm to form a hole injection layer, and the compound according to the present invention was vacuum deposited to a thickness of 60 nm on the hole injection layer.
  • a hole transport layer was formed.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • Ir (ppy) 2,4'-N, N'-dicarbazole-biphenyl
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum
  • a hole blocking layer was formed, and tris (8-quinolinol) aluminum (hereinafter abbreviated as “Alq 3 ”) was vacuum deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Thereafter, LiF, which is a halogenated alkali metal, was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and then an Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.
  • Alq 3 tris (8-quinolinol) aluminum
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example I, except that Comparative Compound A was used instead of the compound according to the present invention as the hole transport layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example I, except that the following Comparative Compound B was used instead of the compound according to the present invention as the hole transport layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example I, except that Comparative Compound C was used instead of the compound according to the present invention, as the hole transport layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example I, except that Comparative Compound D was used instead of the compound according to the present invention, as the hole transport layer material.
  • the forward bias DC voltage was applied to the organic electroluminescent devices according to Experimental Example I (Experimental Example (1) to Experimental Example 76) and Comparative Example I (Comparative Example (1) to Comparative Example (4)) prepared as described above.
  • the electroluminescence (EL) characteristics were measured with a PR-650 photoresearch company, and the T95 life was measured using a life-time measurement device manufactured by McScience Inc. at a luminance of 5000 cd / m 2.
  • Table 4 shows the fabrication of devices for Experimental Example I (Experimental Example (1) to Experimental Example (76)) and Comparative Example I (Comparative Example (1) to Comparative Example (4)) to which the compound according to the present invention was applied and its The evaluation result is shown.
  • the organic electroluminescent device using the organic electroluminescent device material of the present invention as a hole transport layer can significantly improve high luminous efficiency, low driving voltage and lifetime.
  • Comparative Compound A which is NPB
  • Comparative Compound B which is Biscarbazole substituted at 3-3 'position
  • Comparative Compound C which is Biscarbazole substituted at 2-2' position
  • Comparative Compound D which is Biscarbazole substituted at 2-3 'position
  • the compound according to the invention of the ball which is a Biscarbazole substituted at the 2-4 'position showed excellent device results.
  • the comparative compound B is meta
  • the comparative compound C is para
  • the comparative compound D is meta while the compound of the present invention is ortho-positioned. It can be seen that the angle of bending is the largest compared to.
  • the difference between the band gap and the T1 value occurs according to the bonding angle depending on the position at which the two carbazoles are connected, and the difference occurs depending on the efficiency and the lifetime, and the efficiency and the lifetime are o- (otho)> You can see that m- (meta)> p- (para).
  • the band gap and the T1 value increase, the electron blocking ability increases, and the HOMO value is relatively low.
  • the charge balance in the light emitting layer is improved, resulting in an increase in efficiency and lifetime. Judging.
  • NPD 4,4-bis [N- (1-naphthyl) -N on the hole injection layer -Phenylamino] biphenyl
  • CBP is used as a host and bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate (abbreviated as "(piq) 2 Ir (acac)”) is used as a dopant on the light emitting auxiliary layer.
  • the doped mixture was vacuum deposited to a thickness of 30 nm to form a light emitting layer.
  • a hole blocking layer was formed by vacuum depositing BAlq to a thickness of 10 nm on the light emitting layer, and an electron transport layer was formed by vacuum depositing Alq 3 to a thickness of 40 nm on the hole blocking layer.
  • LiF which is a halogenated alkali metal
  • LiF which is a halogenated alkali metal
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example II, except that the emission auxiliary layer was not formed.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example II, except that Comparative Compound B was used instead of the compound according to the present invention.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example II, except that Comparative Compound C was used instead of the compound according to the present invention.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example II, except that Comparative Compound D was used instead of the compound according to the present invention.
  • the forward bias DC voltage was applied to the organic electroluminescent devices according to Experimental Example II (Experimental Example (77) to Experimental Example 114) and Comparative Example II (Comparative Example (5) to Comparative Example (8)) prepared as described above.
  • the electroluminescence (EL) characteristics were measured with a PR-650 photoresearch company, and T95 life was measured using a life-time measurement device manufactured by McScience Inc. at a luminance of 2500 cd / m 2.
  • Table 5 shows the fabrication of devices for Experimental Example II (Experimental Example (77) to Experimental Example 114) and Comparative Example II (Comparative Example (5) to Comparative Example (8)) to which the compound according to the present invention is applied and its The evaluation result is shown.
  • NPD was vacuum-deposited to a thickness of 60nm on the hole injection layer to form a hole transport layer.
  • the compound according to the present invention on the hole transport layer by vacuum deposition to a thickness of 20nm to form a light emitting auxiliary layer.
  • a light emitting layer was formed by vacuum depositing a mixture doped at a 95: 5 weight ratio using CBP as a host and Ir (ppy) 3 as a dopant on the light emitting auxiliary layer.
  • a hole blocking layer was formed by vacuum depositing BAlq to a thickness of 10 nm on the light emitting layer, and an electron transport layer was formed by vacuum depositing Alq 3 to a thickness of 40 nm on the hole blocking layer.
  • LiF which is a halogenated alkali metal, was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and then an Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example III, except that the emission auxiliary layer was not formed.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example III, except that Comparative Compound B was used instead of the compound according to the present invention as a light-emitting auxiliary layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example III, except that Comparative Compound C was used instead of the compound according to the present invention as a light-emitting auxiliary layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example III, except that Comparative Compound D was used instead of the compound according to the present invention.
  • the forward bias DC voltage was applied to the organic electroluminescent devices according to Experimental Example III (Experimental Example 115 to 152) and Comparative Example III (Comparative Example (9) to Comparative Example (12)) prepared as described above.
  • the electroluminescence (EL) characteristics were measured with a PR-650 photoresearch company, and the T95 life was measured using a life-time measurement device manufactured by McScience Inc. at a luminance of 5000 cd / m 2.
  • Table 6 shows the fabrication of devices for Experimental Example III (Experimental Example 115 to Experimental Example 152) and Comparative Example III (Comparative Example (9) to Comparative Example (12)) to which the compound according to the present invention was applied and its The evaluation result is shown.
  • the compound according to the present invention which is Bis-Carbazole substituted at the 2-4 'position as described in Experimental Example I, has a high T1 energy level and a relatively low HOMO energy level, resulting in better charge balance in the light emitting layer. And lifespan is believed to be increased.
  • NPD was vacuum-deposited to a thickness of 60nm on the hole injection layer to form a hole transport layer.
  • a mixture of the compound according to the present invention as a host and Ir (ppy) 3 as a dopant was vacuum deposited to a thickness of 30 nm to form a light emitting layer.
  • a hole blocking layer was formed by vacuum depositing BAlq to a thickness of 10 nm on the light emitting layer, and an electron transport layer was formed by vacuum depositing Alq 3 to a thickness of 40 nm on the hole blocking layer.
  • LiF which is a halogenated alkali metal
  • LiF which is a halogenated alkali metal
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example IV, except that Comparative Compound E was used instead of the compound according to the present invention as a host material of the emission layer.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example IV, except that Comparative Compound F was used instead of the compound according to the present invention as a host material of the emission layer.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example IV, except that Comparative Compound H was used instead of the compound according to the present invention as a host material of the emission layer.
  • the forward bias DC voltage was applied to the organic electroluminescent devices according to Experimental Example IV (Experimental Example 153 to 179) and Comparative Example IV (Comparative Example 13 to Comparative Example 16) prepared as described above.
  • the electroluminescence (EL) characteristics were measured with a PR-650 photoresearch company, and the T95 life was measured using a life-time measurement device manufactured by McScience Inc. at a luminance of 5000 cd / m 2.
  • Table 7 shows device fabrication for Experimental Example IV (Experimental Example (153) to Experimental Example (179)) and Comparative Example IV (Comparative Example (13) to Comparative Example (16)) to which the compound according to the present invention was applied and its The evaluation result is shown.
  • NPD was vacuum-deposited to a thickness of 60nm on the hole injection layer to form a hole transport layer.
  • a light emitting layer was formed by vacuum depositing a mixture of the compound according to the present invention on the hole injection layer as a host and doping at a weight ratio of 95: 5 by using (piq) 2 Ir (acac) as a dopant at a thickness of 30 nm.
  • a hole blocking layer was formed by vacuum depositing BAlq to a thickness of 10 nm on the light emitting layer, and an electron transport layer was formed by vacuum depositing Alq 3 to a thickness of 40 nm on the hole blocking layer.
  • LiF which is a halogenated alkali metal, was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and then an Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example V, except that Comparative Compound E was used instead of the compound according to the present invention as a host material of the emission layer.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example V, except that Comparative Compound F was used instead of the compound according to the present invention as a host material of the emission layer.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example V, except that Comparative Compound G was used instead of the compound according to the present invention as a host material of the emission layer.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example V, except that Comparative Compound H was used instead of the compound according to the present invention as a host material of the emission layer.
  • the forward bias DC voltage is applied to the organic electroluminescent devices according to Experimental Example V (Experimental Example 180 to 237) and Comparative Example V (Comparative Example 17 to Comparative Example 20) prepared as described above.
  • the electroluminescence (EL) characteristics were measured with a PR-650 photoresearch company, and T95 life was measured using a life-time measurement device manufactured by McScience Inc. at a luminance of 2500 cd / m 2.
  • Table 8 shows device fabrication and evaluation results of V (Experimental Example 180 to Experimental Example 237) and Comparative Example V (Comparative Example 17 to Comparative Example 20) to which the compound according to the present invention was applied. Indicates.
  • the organic electroluminescent device using the organic electroluminescent device material of the present invention as a phosphorescent host can significantly improve high luminous efficiency, low driving voltage and lifetime.
  • 2,4'-bis carbazole a self-developed material having a wide band gap, has a HOMO value capable of smoothly receiving holes from the hole transport layer, and thus, exhibits a relatively low driving voltage and a high T1 value. Due to this, energy transfer with the dopant material in the light emitting layer is well performed, and thus it is determined to have high luminous efficiency and lifetime.
  • the evaluation results of the above-described device fabrication described the device characteristics in terms of the hole transport layer, the light emitting auxiliary layer, and the light emitting layer (phosphorescent host).
  • An organic material layer of an organic electric device such as an electron transport layer, an electron injection layer, a hole injection layer, may be used in combination with a single or another material. Therefore, the compounds of the present invention can be used in combination with a single or other material in addition to the hole transport layer, the light emitting auxiliary layer, the light emitting layer (phosphorescent host), for example, an electron transport layer, an electron injection layer, a hole injection layer.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un nouveau composé permettant d'accroître l'efficacité électroluminescente, la stabilité, et la durée de vie d'un élément, un élément électronique organique utilisant celui-ci et un dispositif électronique associé.
PCT/KR2014/009649 2013-10-15 2014-10-14 Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique associé WO2015056965A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020130122324A KR102171124B1 (ko) 2013-10-15 2013-10-15 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR10-2013-0122324 2013-10-15

Publications (1)

Publication Number Publication Date
WO2015056965A1 true WO2015056965A1 (fr) 2015-04-23

Family

ID=52828346

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2014/009649 WO2015056965A1 (fr) 2013-10-15 2014-10-14 Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique associé

Country Status (2)

Country Link
KR (1) KR102171124B1 (fr)
WO (1) WO2015056965A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016204151A1 (fr) * 2015-06-16 2016-12-22 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique, et dispositif électronique
EP3626719A1 (fr) * 2014-04-29 2020-03-25 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
JPWO2021201287A1 (fr) * 2020-04-03 2021-10-07
US11424414B2 (en) 2017-03-29 2022-08-23 Idemitsu Kosan Co., Ltd. Organic electroluminescent element, electronic device, and compound

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102399009B1 (ko) * 2015-05-11 2022-05-17 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20170024418A (ko) * 2015-08-25 2017-03-07 삼성에스디아이 주식회사 유기 화합물, 유기 광전자 소자 및 표시 장치
KR20170027620A (ko) * 2015-09-02 2017-03-10 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 및 이를 포함하는 유기 광전자 소자 및 표시장치
KR102587380B1 (ko) * 2015-12-10 2023-10-12 솔루스첨단소재 주식회사 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
KR102685450B1 (ko) * 2016-12-15 2024-07-16 솔루스첨단소재 주식회사 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자
KR102514842B1 (ko) * 2017-03-28 2023-03-29 도레이 카부시키가이샤 화합물, 그것을 함유하는 전자 디바이스, 유기 박막 발광 소자, 표시 장치 및 조명 장치
KR102337571B1 (ko) * 2017-06-20 2021-12-14 엘티소재주식회사 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
CN109096254B (zh) * 2017-06-20 2021-07-06 江西师范大学 喹唑啉衍生物及其制备方法和应用
JP7187152B2 (ja) * 2018-01-12 2022-12-12 三星電子株式会社 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用組成物、有機エレクトロルミネッセンス素子、及び化合物の製造方法
WO2022075270A1 (fr) * 2020-10-05 2022-04-14 出光興産株式会社 Élément électroluminescent organique, composé, matériau pour élément électroluminescent organique et dispositif électronique

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011137072A1 (fr) * 2010-04-26 2011-11-03 Universal Display Corporation Composés contenant un bicarbazole pour oled
WO2012023947A1 (fr) * 2010-08-20 2012-02-23 Universal Display Corporation Composés de bicarbazole pour dispositifs électroluminescents organiques (oled)
JP2012049518A (ja) * 2010-07-27 2012-03-08 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子材料、化合物、有機エレクトロルミネッセンス素子、表示装置、並びに照明装置
WO2012108389A1 (fr) * 2011-02-07 2012-08-16 出光興産株式会社 Dérivé de bis-carbazole ainsi qu'élément électroluminescent organique mettant en oeuvre celui-ci
JP2012216801A (ja) * 2011-03-28 2012-11-08 Toray Ind Inc 発光素子材料および発光素子

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011137072A1 (fr) * 2010-04-26 2011-11-03 Universal Display Corporation Composés contenant un bicarbazole pour oled
JP2012049518A (ja) * 2010-07-27 2012-03-08 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子材料、化合物、有機エレクトロルミネッセンス素子、表示装置、並びに照明装置
WO2012023947A1 (fr) * 2010-08-20 2012-02-23 Universal Display Corporation Composés de bicarbazole pour dispositifs électroluminescents organiques (oled)
WO2012108389A1 (fr) * 2011-02-07 2012-08-16 出光興産株式会社 Dérivé de bis-carbazole ainsi qu'élément électroluminescent organique mettant en oeuvre celui-ci
JP2012216801A (ja) * 2011-03-28 2012-11-08 Toray Ind Inc 発光素子材料および発光素子

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3626719A1 (fr) * 2014-04-29 2020-03-25 Universal Display Corporation Matériaux et dispositifs électroluminescents organiques
WO2016204151A1 (fr) * 2015-06-16 2016-12-22 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique, et dispositif électronique
US20180145265A1 (en) 2015-06-16 2018-05-24 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence element, organic electroluminescence element, and electronic device
US10170707B2 (en) 2015-06-16 2019-01-01 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence element, organic electroluminescence element, and electronic device
US11424414B2 (en) 2017-03-29 2022-08-23 Idemitsu Kosan Co., Ltd. Organic electroluminescent element, electronic device, and compound
JPWO2021201287A1 (fr) * 2020-04-03 2021-10-07
WO2021201287A1 (fr) * 2020-04-03 2021-10-07 国立大学法人京都大学 1,2-bis(diarylamino)benzène asymétrique, son procédé de production et son application
CN115427391A (zh) * 2020-04-03 2022-12-02 国立大学法人京都大学 非对称1，2－双（二芳基氨基）苯类、其制造方法以及用途
JP7429349B2 (ja) 2020-04-03 2024-02-08 国立大学法人京都大学 非対称１，２－ビス（ジアリールアミノ）ベンゼン類、その製造方法及び用途

Also Published As

Publication number Publication date
KR20150043669A (ko) 2015-04-23
KR102171124B1 (ko) 2020-10-28

Similar Documents

Publication Publication Date Title
WO2015056965A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique associé
WO2016190600A1 (fr) Composé pour élément électrique organique, élément électrique organique utilisant ce composé, et dispositif électronique correspondant
WO2016140497A2 (fr) Composé pour dispositif électrique organique, dispositif électrique organique l'utilisant, et dispositif électronique associé
WO2016003225A2 (fr) Composé pour élément électronique organique, élément électronique organique utilisant ledit composé et dispositif électronique comprenant ledit composé
WO2018016786A1 (fr) Composé pour dispositif électronique organique, dispositif électronique organique l'utilisant et appareil électronique associé
WO2014010910A1 (fr) Composé, élément électronique organique l'utilisant et dispositif électronique associé
WO2015041416A1 (fr) Élément électrique organique utilisant des composés pour un élément électrique organique et dispositif électronique pour ce dernier
WO2014058183A1 (fr) Composé pour dispositif électronique organique, dispositif électronique organique l'utilisant et appareil électronique dudit dispositif électronique organique
WO2016056757A2 (fr) Composé pour élément électro-organique, élément électro-organique et appareil électronique l'utilisant
WO2014178532A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique correspondant
WO2014104585A1 (fr) Composé pour un élément électronique organique, élément électronique organique l'utilisant et son dispositif électronique
WO2016013816A1 (fr) Élément électrique organique faisant appel à un composé pour élément électrique organique, et dispositif électronique associé
WO2015178585A1 (fr) Composé pour dispositif électro-organique, dispositif électro-organique utilisant celui-ci, et dispositif électronique associé
WO2014061960A1 (fr) Composé pour dispositif électroluminescent organique, dispositif électroluminescent organique et dispositif électronique l'utilisant
WO2017052099A1 (fr) Composé pour dispositif électronique organique, dispositif électronique organique l'utilisant et dispositif électronique associé
WO2015080404A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique correspondant
WO2015088183A1 (fr) Composé pour élément organique électrique, élément organique électrique l'utilisant et dispositif électronique correspondant
WO2016032150A2 (fr) Composé pour élément électrique organique, élément électrique organique utilisant ledit composé, et dispositif électronique comprenant ceux-ci
WO2017052129A1 (fr) Nouveau composé pour dispositif électrique organique, dispositif électrique organique l'utilisant et dispositif électronique le comprenant
WO2018169261A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé
WO2020085797A1 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique associé
WO2016153198A1 (fr) Composé pour dispositif électronique organique, dispositif électronique organique l'utilisant et appareil électronique associé
WO2018225991A1 (fr) Composé pour dispositif électrique organique, dispositif électrique organique l'utilisant, et dispositif électronique associé
WO2017014460A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant ce composé et dispositif électronique associé
WO2016013817A2 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique correspondant

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: 14854343

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 14854343

Country of ref document: EP

Kind code of ref document: A1