WO2015041428A1 - Élément électronique organique utilisant un composé pour élément électronique organique et dispositif électronique associé - Google Patents

Élément électronique organique utilisant un composé pour élément électronique organique et dispositif électronique associé Download PDF

Info

Publication number
WO2015041428A1
WO2015041428A1 PCT/KR2014/008399 KR2014008399W WO2015041428A1 WO 2015041428 A1 WO2015041428 A1 WO 2015041428A1 KR 2014008399 W KR2014008399 W KR 2014008399W WO 2015041428 A1 WO2015041428 A1 WO 2015041428A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
organic
layer
light emitting
mmol
Prior art date
Application number
PCT/KR2014/008399
Other languages
English (en)
Korean (ko)
Inventor
문성윤
이선희
김대성
이윤석
소기호
윤진호
오대환
이범성
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 WO2015041428A1 publication Critical patent/WO2015041428A1/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
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/58—Naphthylamines; N-substituted derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/805—Electrodes
    • 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
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/32—Stacked devices having two or more layers, each emitting at different wavelengths
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/93—Spiro compounds
    • C07C2603/94—Spiro compounds containing "free" spiro atoms
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • 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 an organic electric device using the compound for organic electric devices and an electronic device thereof.
  • organic electroluminescence display (organic EL display device) using a light emitting material for the light emitting element of the display portion has been actively developed.
  • the organic EL display device unlike a liquid crystal display device or the like, recombines holes and electrons injected into an anode and a cathode in a light emitting layer, thereby emitting a light emitting material containing an organic compound in the light emitting layer to realize display. Display device.
  • organic electroluminescent element In an organic electroluminescent element (hereinafter referred to as an "organic EL element"), it has recently been proposed to be composed of a plurality of layers having different characteristics such as a light emitting layer and a layer for transporting carriers (holes, electrons) to the light emitting layer. .
  • the hole transport layer has excellent hole transport capacity and carrier resistance.
  • various hole transport materials have been proposed.
  • Patent Document 1 using a carbazole derivative as a hole transport layer and an amine compound having deuterium are used as a structure in which a simple aryl group is substituted with the Patent Documents 2 and 3 amine structures used as host materials for the hole transport material and the light emitting layer.
  • Patent Document 3 used as a transport material, Patent Document 4 and the like in which an amine compound having a fluorenyl group are used as a hole transport material or an injection material have been reported.
  • Patent Document 0001 US Patent Application Publication No. 2007/0231503
  • Patent Document 0002 International Publication No. 2012/091471
  • Patent Document 0003 Korean Patent Application Publication No. 2000/0052560
  • Patent Document 0004 International Publication No. 2010/110553
  • An object of the present invention is to provide an organic electroluminescent device having improved device and efficiency by preventing interfacial degradation of the light emitting layer and increasing charge balance in the light emitting layer, and an organic light emitting material for realizing the same, and an electronic device using the same.
  • a light emitting auxiliary layer (multiple hole transport layer) must exist between the hole transport layer and the light emitting layer. It is time to develop the auxiliary layer.
  • 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 form recombination in the light emitting layer to form excitons.
  • positive polaron accumulates at the interface between the light emitting layer and the hole transport layer.
  • interfacial deterioration occurs, resulting in longevity and efficiency.
  • excess polaron in the light emitting layer attacks weak bonding of the light emitting material, which deforms the light emitting material, resulting in a decrease in lifespan and efficiency and a decrease in color purity. Indicates.
  • the light emitting auxiliary layer should be a material having a suitable HOMO value between the light emitting layer and the hole transport layer in order to prevent the positive polaron from accumulating at the light emitting layer interface between the hole transport layer and the light emitting layer.
  • it In order to increase the balance, it must be a material having hole mobility within a suitable driving voltage range (in the blue device driving voltage range of the full device).
  • the present invention has been made in view of the above problems, and an object thereof is to provide an organic electroluminescent device having improved device and efficiency by preventing interfacial degradation of the light emitting layer and increasing charge balance in the light emitting layer, and an organic light emitting material for realizing the same.
  • the present invention provides an organic electronic device using the compound represented by the following formula and an electronic device thereof.
  • the organic material layer including at least a hole transport layer, a light emitting auxiliary layer and a light emitting layer, wherein the hole transport layer is present between the first electrode and the light emitting auxiliary layer.
  • 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 or an aromatic ring having 6 to 60 carbon atoms or 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 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 organic material layer including at least a hole transport layer, a light emitting auxiliary layer, and a light emitting layer, wherein the hole transport layer is present between the first electrode and the light emitting auxiliary layer.
  • Ar 0 to Ar 2 , and Ar 6 to Ar 11 are each independently i) a C 6 to 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 -LN (R a ) (R b ); or ii) Ar 1 and Ar 2 may be bonded to each other to form a ring, wherein the 'ring' is an aliphatic C 3 to C 60 refers to a ring, a C 6 ⁇ C 60 aromatic, C 2 ⁇ C 60 of the heterocycle or a combination thereof is a
  • Ar 4 and Ar 5 are i) independently of each other hydrogen; C 1 ⁇ C 50 Alkyl group; 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; or ii) Ar 4 and Ar 5 are bonded to each other to combine Together with fluorene it is possible to form spiro compounds.
  • a, b, c, d, e, f and g are integers from 0 to 4,
  • R 0 to R 6 are i) independently of each other deuterium; 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 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 -LN (R a ) (R b ); or ii) when a, b, c, d, e, f and g are each an integer of 2 or more, R 0 to R 6 are each neighbor
  • the substituents may be bonded to each other to form at least one ring, wherein the 'ring' is an aliphatic
  • L 1 to L 6 and L are independently of each other a single bond; 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 a C 2 to C 60 heterocyclic group including at least one heteroatom of O, N, S, Si, and P; wherein L 3 to L 5 exclude a single bond.
  • 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.
  • the hole transport layer comprises a compound represented by the formula (1)
  • the light emitting auxiliary layer is an organic electric device, characterized in that one of the compounds represented by the formula (2) to formula (4) to provide.
  • the compound represented by Formula 2 of the light emitting auxiliary layer may be one of the following compounds.
  • the compound represented by Formula 3 of the light emitting auxiliary layer may be one of the following compounds.
  • the compound represented by Formula 4 of the light emitting auxiliary layer may be one of the following compounds.
  • the compound represented by Formula 1 of the hole transport layer may be one of the following compounds.
  • an organic electric device comprising a light efficiency improving 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
  • the organic material layer is provided by any one of a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process and a roll-to-roll process do.
  • 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.
  • the compound represented by Formula 1 according to the present invention may be synthesized by the reaction route of Scheme 1 below, but is not limited thereto.
  • the L * is an L 5 or L 6 as defined in Ar 3 of formula (1).
  • Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2, but is not limited thereto.
  • S1 to S7 are as follows.
  • Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 12, but is not limited thereto.
  • Sub 3 of Scheme 1 may be synthesized by the reaction route of Scheme 19, but is not limited thereto.
  • N- (4'-bromo- [1,1'-biphenyl] -4-yl) -N-phenylnaphthalen-1-amine (10.8 g, 24 mmol) is dissolved in toluene, followed by N-phenylnaphthalen-1-amine (4.4 g, 20 mmol), Pd 2 (dba) 3 (0.05 equiv), PPh 3 (0.1 equiv) and NaO t -Bu (3 equiv) were then added and stirred under reflux at 100 ° C. for 24 hours.
  • Compound represented by Formula 2 according to the present invention (Final Product) may be synthesized by the reaction route of Scheme 23, but is not limited thereto.
  • Sub 4 of Scheme 23 may be synthesized by the reaction route of Scheme 24, but is not limited thereto.
  • Sub 5 of Scheme 23 may be synthesized by the reaction route of Scheme 25, but is not limited thereto.
  • methyl-4-chloro-2-hydroxybenzoate (100g, 537mmol) is dissolved in 1000mL of methylene chloride and triethylamine (113mL, 805mmol) is added.
  • Trifluoromethanesulfonic anhydride (99 mL, 590 mmol) is added dropwise at -78 ° C and the temperature is gradually raised to room temperature. After the reaction, the mixture was extracted with water and the organic layer was removed with MgSO 4 and filtered. Remove organic solvent, dissolve with ether, separate silicagel column, remove dark color, remove solvent and vacuum dry.
  • Methyl-4-chloro-2-(((trifluoromethyl) sulfonyl) oxy) benzoate (156g, 492mmol), Phenylbronicacid (60g, 492mmol), Pd (PPh 3 ) 4 (11g, 10mmol) and potassium carbonate ( 102 g, 738 mmol) and 1000 mL of DMF were added and stirred at 110 ° C. After the reaction, the mixture was extracted with ether and water, and the organic layer was removed with MgSO 4 and filtered. The organic solvent is removed, the silicagel column is separated and the solvent is removed and dried in vacuo.
  • the compound represented by Chemical Formula 3 according to the present invention may be synthesized by the reaction route of Scheme 32, but is not limited thereto.
  • Sub 6 of Scheme 32 may be synthesized by the reaction route of Scheme 33, but is not limited thereto.
  • Sub 6-2 (16.46 g, 98.4 mmol) obtained in the above synthesis was dissolved in toluene in a round bottom flask, followed by 4-bromo-4'-iodo-1,1'-biphenyl (70.68 g, 196.9 mmol) and Pd 2 (dba) 3 (2.7 g, 3 mmol), 50% P ( t -Bu) 3 (3.8 ml, 7.9 mmol), NaO t -Bu (28.38 g, 295.3 mmol) was added and stirred at 70 ° C.
  • Sub 7 of Scheme 40 may be synthesized by the reaction route of Scheme 41, but is not limited thereto.
  • N 1- (naphthalen-2-yl) -N 4 , N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl) -N 1- phenylbenzene-1,4-diamine (hereinafter abbreviated as "2-TNATA") was vacuum deposited to a thickness of 60 nm to form a hole injection layer, and then the compound represented by Formula 1 of the present invention on the hole injection layer Vacuum deposition to a thickness of 60nm to form a hole transport layer.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • host bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate
  • (piq) 2 Ir (acac)) as a dopant, and the mixture doped at 95: 5 weight was vacuum deposited to a thickness of 30 nm to form a light emitting layer.
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolineoleito) aluminum
  • BAlq 3 tris (8-quinolinol) aluminum
  • LiF an alkali metal halide
  • the forward bias DC voltage was applied to the organic electroluminescent devices according to Experimental Example I (Experimental Example (1) to Experimental Example 30) and Comparative Example I (Comparative Example (1) to Comparative Example (3)) 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 10 shows device fabrication for Experimental Example I (Experimental Example (1) to Experimental Example (30)) and Comparative Example I (Comparative Example (1) to Comparative Example (3)) to which the compound according to the present invention was applied. And the evaluation result.
  • a hole injection layer is formed by vacuum depositing 2-TNATA with a thickness of 60 nm on an ITO layer (anode) formed on a glass substrate, and then vacuuming the compound represented by Formula 1 of the present invention on the hole injection layer with a thickness of 60 nm. It was deposited to form a hole transport layer. Subsequently, one of the compounds represented by Formulas 2 to 4 of the present invention was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emitting auxiliary layer.
  • LiF an alkali metal halide
  • the forward bias DC voltage was applied to the organic electroluminescent devices according to Experimental Example II (Experimental Example (31) to Experimental Example (60)) and Comparative Example II (Comparative Example (4) to Comparative Example (6)) 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 11 shows device fabrication of Experimental Example II (Experimental Example (31) to Experimental Example (60)) and Comparative Example II (Comparative Example (4) to Comparative Example (6)) to which the compound according to the present invention was applied. And the evaluation result.
  • a hole injection layer is formed by vacuum depositing 2-TNATA with a thickness of 60 nm on an ITO layer (anode) formed on a glass substrate, and then vacuuming the compound represented by Formula 1 of the present invention on the hole injection layer with a thickness of 60 nm. It was deposited to form a hole transport layer. Subsequently, one of the compounds represented by Formulas 2 to 4 of the present invention was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emitting auxiliary layer.
  • a mixture doped with 9,10-di (naphthalen-2-yl) anthracene as a host and BD-052X (manufactured by Idemitsukosan) as a dopant at 93: 7 weight was 30 nm thick.
  • Evaporation was carried out in vacuo to form a light emitting layer.
  • BAlq was vacuum deposited on the emission layer to form a hole blocking layer, and Alq 3 was deposited on the hole blocking layer to 40 nm in thickness to form an electron transport layer.
  • LiF an alkali metal halide
  • An organic electric device was manufactured in the same manner as in Experimental Example III, except that the light emitting auxiliary layer was not formed.
  • the forward bias DC voltage was applied to the organic electroluminescent devices according to Experimental Example III (Experimental Example (61) to Experimental Example 90) and Comparative Example III (Comparative Example (7) to Comparative Example (9)) prepared as described above.
  • the electroluminescence (EL) characteristics were measured with a PR-650 photoresearch company, and T95 life was measured using a life measurement device manufactured by McScience Inc. at a luminance of 500 cd / m 2.
  • Table 12 shows device fabrication for Experimental Example III (Experimental Example (61) to Experimental Example (90)) and Comparative Example III (Comparative Example (7) to Comparative Example (9)) to which the compound according to the present invention was applied. And the evaluation result.
  • the compound of the present invention substituted with position 3 of fluorene alone is used as the light emitting auxiliary layer, it has a high T1 energy level and a deep HOMO energy level. It is believed that the light emission is performed inside the light emitting layer instead of the interface to maximize the efficiency.
  • the device characteristics were described in terms of the hole transport layer and the light emitting auxiliary layer.
  • the organic material layer of the organic electric element such as the light emitting layer may be used in a single or mixed with other materials. Therefore, the compounds of the present invention can be used in a single or other material mixed with other organic material layers, for example, electron injection layer, electron transport layer, hole injection layer and the light emitting layer in addition to the hole transport layer or the light emitting auxiliary 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 élément électronique organique comprenant une première électrode, une seconde électrode et une couche de matières organiques située entre la première et la seconde électrode et comprenant au moins une couche de transport à trous, une couche auxiliaire d'émission lumineuse et une couche d'émission lumineuse. Ladite couche de transport à trous comprend un composé exprimé par la formule chimique (1), et la couche auxiliaire d'émission lumineuse comprend au moins un composé parmi les composés exprimés par les formules chimiques (2)-(4).
PCT/KR2014/008399 2013-09-17 2014-09-05 Élément électronique organique utilisant un composé pour élément électronique organique et dispositif électronique associé WO2015041428A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020130111663A KR102072756B1 (ko) 2013-09-17 2013-09-17 유기전기 소자용 화합물을 이용한 유기전기소자 및 그 전자 장치
KR10-2013-0111663 2013-09-17

Publications (1)

Publication Number Publication Date
WO2015041428A1 true WO2015041428A1 (fr) 2015-03-26

Family

ID=52689049

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2014/008399 WO2015041428A1 (fr) 2013-09-17 2014-09-05 Élément électronique organique utilisant un composé pour élément électronique organique et dispositif électronique associé

Country Status (2)

Country Link
KR (1) KR102072756B1 (fr)
WO (1) WO2015041428A1 (fr)

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016006709A1 (fr) * 2014-07-11 2016-01-14 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique
CN105609662A (zh) * 2015-12-22 2016-05-25 成都新柯力化工科技有限公司 一种钙钛矿光伏材料专用的空穴传输材料的制备方法
US20160164002A1 (en) * 2013-07-30 2016-06-09 Merck Patent Gmbh Materials for electronic devices
WO2016111301A1 (fr) * 2015-01-08 2016-07-14 保土谷化学工業株式会社 Élément électroluminescent organique
US20170012212A1 (en) * 2014-01-22 2017-01-12 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
CN106565592A (zh) * 2015-12-09 2017-04-19 广东阿格蕾雅光电材料有限公司 有机空穴传输材料
CN106848060A (zh) * 2016-12-26 2017-06-13 广东阿格蕾雅光电材料有限公司 基于非对称有机空穴传输材料的仅空穴半导体二极管器件
CN106866499A (zh) * 2016-12-26 2017-06-20 广东阿格蕾雅光电材料有限公司 有机空穴传输材料
WO2017102063A1 (fr) * 2015-12-16 2017-06-22 Merck Patent Gmbh Matières pour dispositifs électroluminescents organiques
CN107266436A (zh) * 2017-06-30 2017-10-20 长春海谱润斯科技有限公司 一种有机光电材料及其制备方法和应用
CN107827873A (zh) * 2017-10-23 2018-03-23 长春海谱润斯科技有限公司 一种三芳胺类衍生物及其有机发光器件
CN107963973A (zh) * 2016-10-20 2018-04-27 东进世美肯株式会社 新颖化合物及包含其的有机发光器件
WO2018095392A1 (fr) 2016-11-23 2018-05-31 广州华睿光电材料有限公司 Mélange organique, composition et composant électronique organique
JPWO2017122813A1 (ja) * 2016-01-14 2018-11-08 保土谷化学工業株式会社 有機エレクトロルミネッセンス素子
CN108929234A (zh) * 2018-07-05 2018-12-04 长春海谱润斯科技有限公司 一种芳香胺类衍生物及其有机电致发光器件
US10170707B2 (en) 2015-06-16 2019-01-01 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence element, organic electroluminescence element, and electronic device
JP2019506369A (ja) * 2015-12-16 2019-03-07 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンス素子のための材料
CN109485577A (zh) * 2017-09-13 2019-03-19 东进世美肯株式会社 新颖化合物及包含其的有机发光器件
JP2019510011A (ja) * 2016-03-03 2019-04-11 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンスデバイスのための材料
CN110892539A (zh) * 2017-07-27 2020-03-17 Sfc株式会社 能够低电压驱动且具有高效率、长寿命特性的有机发光元件
US11302870B2 (en) 2016-11-02 2022-04-12 Merck Patent Gmbh Materials for electronic devices
US20220278285A1 (en) * 2017-09-29 2022-09-01 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element comprising the same, and electronic device thereof
US11649225B2 (en) 2017-10-27 2023-05-16 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound and organic electroluminescent device comprising the same

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10840454B2 (en) 2013-06-14 2020-11-17 Samsung Display Co., Ltd. Organic light-emitting devices
US11895909B2 (en) 2015-04-29 2024-02-06 Samsung Display Co., Ltd. Organic light-emitting device
EP4236652A3 (fr) 2015-07-29 2023-09-13 Merck Patent GmbH Matériaux pour dispositifs électroluminescents organiques
KR101614738B1 (ko) * 2015-11-02 2016-04-22 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
WO2017090919A1 (fr) * 2015-11-26 2017-06-01 덕산네오룩스 주식회사 Composé pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique le comprenant
KR102616579B1 (ko) * 2016-04-08 2023-12-22 삼성디스플레이 주식회사 유기 발광 소자
KR102406212B1 (ko) * 2017-05-31 2022-06-10 주식회사 동진쎄미켐 캡핑층 형성용 화합물 및 이를 포함하는 유기 발광 소자
WO2019083248A1 (fr) * 2017-10-27 2019-05-02 Rohm And Haas Electronic Materials Korea Ltd. Composé électroluminescent organique et dispositif électroluminescent organique le comprenant
CN110128330A (zh) * 2018-02-09 2019-08-16 北京鼎材科技有限公司 芳胺衍生物及其应用和有机电致发光器件
JPWO2022071350A1 (fr) 2020-09-30 2022-04-07
CN112194612A (zh) * 2020-10-15 2021-01-08 濮阳惠成电子材料股份有限公司 光电材料中间体n-(7-溴-9,9-二甲基芴-2-基）咔唑的合成方法
KR102438159B1 (ko) * 2021-05-24 2022-08-30 덕산네오룩스 주식회사 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030165712A1 (en) * 2001-12-27 2003-09-04 Lightronik Technology Inc. Organic EL Device
KR20100054110A (ko) * 2008-11-13 2010-05-24 주식회사 엘지화학 저전압 구동 유기발광소자 및 이의 제조 방법
KR101181281B1 (ko) * 2012-03-13 2012-09-10 덕산하이메탈(주) 광효율 개선층을 포함하는 유기전기소자, 이를 포함하는 전자 장치 및 이에 이용되는 유기전기소자용 화합물
KR20130025854A (ko) * 2011-09-02 2013-03-12 주식회사 엘엠에스 유기전자소자 및 그 제조방법
KR20130084960A (ko) * 2012-01-18 2013-07-26 덕산하이메탈(주) 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101389527B1 (ko) 2013-09-17 2014-04-25 덕산하이메탈(주) 유기전기 소자용 화합물을 이용한 유기전기소자 및 그 전자 장치

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030165712A1 (en) * 2001-12-27 2003-09-04 Lightronik Technology Inc. Organic EL Device
KR20100054110A (ko) * 2008-11-13 2010-05-24 주식회사 엘지화학 저전압 구동 유기발광소자 및 이의 제조 방법
KR20130025854A (ko) * 2011-09-02 2013-03-12 주식회사 엘엠에스 유기전자소자 및 그 제조방법
KR20130084960A (ko) * 2012-01-18 2013-07-26 덕산하이메탈(주) 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR101181281B1 (ko) * 2012-03-13 2012-09-10 덕산하이메탈(주) 광효율 개선층을 포함하는 유기전기소자, 이를 포함하는 전자 장치 및 이에 이용되는 유기전기소자용 화합물

Cited By (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20160164002A1 (en) * 2013-07-30 2016-06-09 Merck Patent Gmbh Materials for electronic devices
US10217944B2 (en) * 2014-01-22 2019-02-26 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
US20170012212A1 (en) * 2014-01-22 2017-01-12 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
WO2016006709A1 (fr) * 2014-07-11 2016-01-14 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique
WO2016006710A1 (fr) * 2014-07-11 2016-01-14 出光興産株式会社 Composé, matériau pour élément électroluminescent organique, élément électroluminescent organique et dispositif électronique
CN105658619A (zh) * 2014-07-11 2016-06-08 出光兴产株式会社 化合物、有机电致发光元件用材料、有机电致发光元件和电子仪器
US10516112B2 (en) 2014-07-11 2019-12-24 Idemitsu Kosan Co., Ltd. Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device
US10854822B2 (en) 2014-07-11 2020-12-01 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent element, organic electroluminescent element, and electronic device
US10944057B2 (en) 2014-07-11 2021-03-09 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescence devices, organic electroluminescence device, and electronic equipment
JPWO2016111301A1 (ja) * 2015-01-08 2017-10-19 保土谷化学工業株式会社 有機エレクトロルミネッセンス素子
WO2016111301A1 (fr) * 2015-01-08 2016-07-14 保土谷化学工業株式会社 Élément électroluminescent organique
US10505119B2 (en) 2015-01-08 2019-12-10 Hodogaya Chemical Co., Ltd. Organic electroluminescence 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
CN106565592A (zh) * 2015-12-09 2017-04-19 广东阿格蕾雅光电材料有限公司 有机空穴传输材料
WO2017097152A1 (fr) * 2015-12-09 2017-06-15 广东阿格蕾雅光电材料有限公司 Matériau organique de transport de trous
CN106565592B (zh) * 2015-12-09 2019-06-25 广东阿格蕾雅光电材料有限公司 有机空穴传输材料
US10374169B2 (en) 2015-12-09 2019-08-06 Guangdong Aglaia Optoelectronic Materials Co. Ltd Organic hole transport material
JP2023011548A (ja) * 2015-12-16 2023-01-24 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンス素子のための材料
CN108368054B (zh) * 2015-12-16 2022-09-02 默克专利有限公司 用于有机电致发光器件的材料
TWI754625B (zh) * 2015-12-16 2022-02-11 德商麥克專利有限公司 用於有機電激發光裝置之材料
CN108368054A (zh) * 2015-12-16 2018-08-03 默克专利有限公司 用于有机电致发光器件的材料
WO2017102063A1 (fr) * 2015-12-16 2017-06-22 Merck Patent Gmbh Matières pour dispositifs électroluminescents organiques
JP2019506369A (ja) * 2015-12-16 2019-03-07 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンス素子のための材料
CN105609662A (zh) * 2015-12-22 2016-05-25 成都新柯力化工科技有限公司 一种钙钛矿光伏材料专用的空穴传输材料的制备方法
TWI740881B (zh) * 2016-01-14 2021-10-01 日商保土谷化學工業股份有限公司 有機電致發光元件
EP3404735B1 (fr) * 2016-01-14 2023-05-10 Hodogaya Chemical Co., Ltd. Élément électroluminescent organique
JPWO2017122813A1 (ja) * 2016-01-14 2018-11-08 保土谷化学工業株式会社 有機エレクトロルミネッセンス素子
JP7080821B2 (ja) 2016-03-03 2022-06-06 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンスデバイスのための材料
JP2019510011A (ja) * 2016-03-03 2019-04-11 メルク パテント ゲーエムベーハー 有機エレクトロルミネッセンスデバイスのための材料
US10961230B2 (en) 2016-03-03 2021-03-30 Merck Patent Gmbh Materials for organic electroluminescent devices
CN107963973A (zh) * 2016-10-20 2018-04-27 东进世美肯株式会社 新颖化合物及包含其的有机发光器件
CN107963973B (zh) * 2016-10-20 2023-07-25 东进世美肯株式会社 新颖化合物及包含其的有机发光器件
US11302870B2 (en) 2016-11-02 2022-04-12 Merck Patent Gmbh Materials for electronic devices
WO2018095392A1 (fr) 2016-11-23 2018-05-31 广州华睿光电材料有限公司 Mélange organique, composition et composant électronique organique
CN106866499B (zh) * 2016-12-26 2020-01-10 广东阿格蕾雅光电材料有限公司 有机空穴传输材料
WO2018120975A1 (fr) * 2016-12-26 2018-07-05 广东阿格蕾雅光电材料有限公司 Matériau organique de transport de trous
CN106866499A (zh) * 2016-12-26 2017-06-20 广东阿格蕾雅光电材料有限公司 有机空穴传输材料
CN106848060A (zh) * 2016-12-26 2017-06-13 广东阿格蕾雅光电材料有限公司 基于非对称有机空穴传输材料的仅空穴半导体二极管器件
CN107266436A (zh) * 2017-06-30 2017-10-20 长春海谱润斯科技有限公司 一种有机光电材料及其制备方法和应用
CN110892539A (zh) * 2017-07-27 2020-03-17 Sfc株式会社 能够低电压驱动且具有高效率、长寿命特性的有机发光元件
CN110892539B (zh) * 2017-07-27 2023-10-31 Sfc株式会社 能够低电压驱动且具有高效率、长寿命特性的有机发光元件
CN109485577A (zh) * 2017-09-13 2019-03-19 东进世美肯株式会社 新颖化合物及包含其的有机发光器件
CN109485577B (zh) * 2017-09-13 2023-12-01 东进世美肯株式会社 新颖化合物及包含其的有机发光器件
US20220278285A1 (en) * 2017-09-29 2022-09-01 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element comprising the same, and electronic device thereof
CN107827873B (zh) * 2017-10-23 2020-02-07 长春海谱润斯科技有限公司 一种三芳胺类衍生物及其有机发光器件
CN107827873A (zh) * 2017-10-23 2018-03-23 长春海谱润斯科技有限公司 一种三芳胺类衍生物及其有机发光器件
US11649225B2 (en) 2017-10-27 2023-05-16 Rohm And Haas Electronic Materials Korea Ltd. Organic electroluminescent compound and organic electroluminescent device comprising the same
CN108929234A (zh) * 2018-07-05 2018-12-04 长春海谱润斯科技有限公司 一种芳香胺类衍生物及其有机电致发光器件

Also Published As

Publication number Publication date
KR102072756B1 (ko) 2020-02-03
KR20150031892A (ko) 2015-03-25

Similar Documents

Publication Publication Date Title
WO2015041428A1 (fr) Élément électronique organique utilisant un composé pour élément électronique organique et dispositif électronique associé
WO2016167491A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant ce composé, et appareil électronique
WO2017090918A1 (fr) Composé pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique le comprenant
WO2015182872A1 (fr) Composé pour élément électro-organique, et élément électro-organique et dispositif électronique utilisant celui-ci
WO2017095075A1 (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
WO2016148425A2 (fr) Composé pour dispositif électrique organique, dispositif électrique organique utilisant ce composé, et dispositif électronique correspondant
WO2015194791A2 (fr) Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique associé
WO2016122150A2 (fr) Composé pour élément électronique organique, élément électronique organique utilisant ce composé et dispositif électronique associé
WO2015130069A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et dispositif électronique associé
WO2016117848A1 (fr) Composé pour dispositif électroluminescent organique et dispositif électroluminescent organique comprenant celui-ci
WO2017082556A1 (fr) Nouveau composé électroluminescent organique et dispositif électroluminescent organique le comprenant
WO2016017919A2 (fr) Dérivé de fluorène condensé comprenant un hétérocycle
WO2017030307A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant celui-ci et appareil électronique comprenant celui-ci
WO2015178585A1 (fr) Composé pour dispositif électro-organique, dispositif électro-organique utilisant celui-ci, et dispositif électronique associé
WO2014088284A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant celui-ci, et dispositif électronique le comprenant
WO2015115756A1 (fr) Composé destiné à un élément électrique organique, élément électrique organique ayant recours à ce composé, et dispositif électronique correspondant
WO2016003202A2 (fr) Composé pour élément électronique organique, élément électronique organique ayant recours à ce composé, et dispositif électronique comportant cet élément
WO2016200070A2 (fr) Composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique comprenant ledit composé
WO2015041416A1 (fr) Élément électrique organique utilisant des composés pour un élément électrique organique et dispositif électronique pour ce dernier
WO2016032150A2 (fr) Composé pour élément électrique organique, élément électrique organique utilisant ledit composé, et dispositif électronique comprenant ceux-ci
WO2013122364A2 (fr) Composé pour élément électrique organique, élément électrique organique le comprenant et dispositif électronique avec celui-ci
WO2016129861A1 (fr) Nouveau composé pour élément électrique organique, élément électrique organique l'utilisant et dispositif électronique comprenant ledit composé
WO2017119654A1 (fr) Composé pour élément électronique organique, élément électronique organique utilisant ce composé, et appareil électronique correspondant
WO2013108997A1 (fr) Composé pour dispositif électronique organique, dispositif électronique organique et appareil électronique le comprenant

Legal Events

Date Code Title Description
NENP Non-entry into the national phase

Ref country code: DE

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

Ref document number: 14845292

Country of ref document: EP

Kind code of ref document: A1

122 Ep: pct application non-entry in european phase

Ref document number: 14845292

Country of ref document: EP

Kind code of ref document: A1