WO2014077558A1 - Composé pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique associé - Google Patents

Composé pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique associé Download PDF

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WO2014077558A1
WO2014077558A1 PCT/KR2013/010220 KR2013010220W WO2014077558A1 WO 2014077558 A1 WO2014077558 A1 WO 2014077558A1 KR 2013010220 W KR2013010220 W KR 2013010220W WO 2014077558 A1 WO2014077558 A1 WO 2014077558A1
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group
sub
mmol
organic
synthesis
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Korean (ko)
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이범성
최연희
이선희
김대성
소기호
윤진호
오대환
박성제
문성윤
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덕산하이메탈(주)
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Priority claimed from KR1020130130267A external-priority patent/KR101455156B1/ko
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Priority to CN201380059200.8A priority Critical patent/CN104781233B/zh
Priority to US14/442,608 priority patent/US9515269B2/en
Publication of WO2014077558A1 publication Critical patent/WO2014077558A1/fr

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers

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 emitting auxiliary according to each light emitting layer (R, G, B). 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. Supported by 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 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 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 It may be used as a material.
  • the compound of the present invention may be used as the light emitting layer 150, hole transport layer 140 and / or light emitting auxiliary layer 151.
  • band gaps, electrical characteristics, and interface characteristics may vary depending on which substituents are bonded at which positions, and thus, the selection of cores and the combination of sub-substituents bonded thereto are very significant.
  • long life and high efficiency can be achieved at the same time when an optimal combination of energy level and T1 value and intrinsic properties (mobility, interfacial properties, etc.) of each organic material layer is achieved.
  • a light emitting auxiliary layer between the hole transport layer and the light emitting layer, and according to each of the light emitting layers R, G, and B, It is time to develop different light emitting auxiliary layers. Meanwhile, in the case of the light emitting auxiliary layer, it is difficult to infer the characteristics of the organic material layer used even if a similar core is used, since the correlation between the hole transport layer and the light emitting layer (host) must be understood.
  • a light emitting layer or an auxiliary light emitting layer using a compound represented by the formula (1) by optimizing the energy level (level) and T1 value between each organic material layer, the intrinsic properties (mobility, interface characteristics, etc.) of the organic material
  • the life and efficiency of the electric device can be improved at the same time.
  • 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).
  • a ring is C 10 ⁇ C 60 Aromatic ring group; Or a C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si, and P; preferably, naphthalene or phenanthrene.
  • Ar 1 to Ar 3 are independently of each other C 6 ⁇ C 60 An aryl group; Fluorenyl groups; C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of O, N, S, Si and P; A fused ring group of an aromatic ring of C 6 ⁇ C 60 and an aliphatic ring of C 3 ⁇ C 60 ; C 1 ⁇ C 50 Alkyl group; And C 2 ⁇ C 20 Alkenyl group; It is selected from the group consisting of,
  • L is a single bond; C 6 ⁇ C 60 arylene group; And fluorenylene group; It is selected from the group consisting of.
  • aromatic ring group, aryl group, fluorenyl group, heterocyclic group, fused ring group, alkyl group, alkenyl group, arylene group, fluorenylene group is each deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; -L'-N (R a ) (R b Where L 'is a single bond; C 6 ⁇ C 60 Arylene group; Fluorenylene groups; C containing at least one heteroatom of O, N, S, Si and P 2 ⁇ C 60 Heterocyclic group of; C 3 ⁇ C 60 Aliphatic ring and C 6 ⁇ C 60 Fused ring group of an aromatic ring of; And divalent C One ⁇ C 60 An aliphatic hydrocarbon group; selected from the group consisting of a And R b Are independently of each other 6 ⁇ C 60 Aryl group; Fluorenyl groups; C containing at least one heteroatom of
  • Chemical Formula 1 may be represented by one of the following chemical formulas.
  • Ar 1 to Ar 3 in Formulas A1 to C8 are the same as defined in Formula 1.
  • Ar 1 to Ar 3 in Formulas A1 to C8 may be any one of the following H1 to H22 independently of each other.
  • Ar 1 to Ar 3 may be independently substituted with one of the substituents of any one of the following H1 to H22, more specifically Ar 1 may be substituted with one of the following H1 to H20, Ar 2 and Ar 3 is Independently of each other it may be substituted with one of the following H1 to H18, H21 and H22.
  • Tables 1 to 8 show examples in which Ar 1 to Ar 3 in Formulas A1 to C8 are one of H1 to H22, and the first two letters of the individual compounds represent Formulas A1 to C8. it means.
  • Formula A1 is one of A1-1 to A1-104 of the following table
  • Formula B1 is one of B1-1 to B1-86 of the following table
  • Formula C1 is C1-1 to C1-86 of the following table
  • Formula A2 is one of A2-1 to A2-24 in the following table
  • Formula B2 is one of B2-1 to B2-10 in the following table
  • Formula C2 is C2-1 to C2-12 in the following table
  • Formula A3 is one of A3-1 to A3-24 in the following table
  • Formula B3 is one of B3-1 to B3-10 in the following table
  • Formula C3 is C3-1 to C3- in the following table Is one of 12
  • Formula A4 is one of A4-1 to A4-24 in the following table
  • Formula B4 is one of B4-1 to B4-10 in the following table
  • Formula C4 is C4-1 to C4 in the following table One of -12
  • Formula A5 is one of A5-1 to A5-24 in the following table
  • Formula B5 is one of B
  • Ar 1 is H1
  • Ar 2 is H5
  • Ar 3 is H4 in Formula A1
  • it may be represented as in the following Formula, which corresponds to Compound A1-5.
  • Ar 1 to Ar 3 of Formula A1 to Formula C8 may combine Compounds A1-1 to C8-12 as described above by the following combinations.
  • 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 electronic device including one of the compounds represented by Formulas A1 to C8 in the organic material layer. More specifically, the present invention provides an organic electroluminescent device comprising a compound represented by the combination of Tables 1 to 8 in the organic material 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 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 a hole transport layer in the organic material layer, the hole transport layer comprises the compound.
  • 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 (Final Product) according to the present invention is synthesized 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-II-B1-4 (55.17g, 186.3mmol) obtained in the above synthesis was prepared with 1-iodonaphthalene (70.99g, 279.4mmol), Na 2 SO 4 (26.46g, 186.3mmol), K 2 CO 3 (25.75g , 186.3 mmol), Cu (3.55 g, 55.9 mmol) and nitrobenzene were obtained using the Sub 1-III-A1-1 synthesis to obtain 56.64 g (yield: 72%) of the product.
  • Sub 1-III-B1-4 (56.64g, 134.1mmol) obtained in the above synthesis to Bis (pinacolato) diboron (37.46g, 147.5mmol), Pd (dppf) Cl 2 (3.29g, 4mmol), KOAc (39.49g) , 402.3 mmol), and DMF were used to obtain 49.73 g (yield: 79%) of the product using the Sub 1-IV-A1-1 synthesis method.
  • Phenanthren-9-ylboronic acid (82.21g, 370.2mmol) as starting material, 2,4-dibromo-1-nitrobenzene (156g, 555.3mmol), Pd (PPh 3 ) 4 (21.39g, 18.5mmol), K 2 CO 3 (153.51 g, 1110.7 mmol), THF, and water were obtained using the Sub 1-I-A1-1 synthesis method to obtain 79.82 g (yield: 57%) of the product.
  • Sub 1-I-C1-1 (79.82g, 211mmol) obtained in the above synthesis of triphenylphosphine (138.39g, 527.6mmol) and o -dichlorobenzene using the Sub 1-II-A1-1 synthesis method 49.69g (yield) : 68%).
  • Sub 1-II-C1-1 (49.69g, 143.5mmol) obtained in the above synthesis was iodobenzene (43.92g, 215.3mmol), Na 2 SO 4 (20.39g, 143.5mmol), K 2 CO 3 (19.84g, 143.5 mmol), Cu (2.74 g, 43.1 mmol) and nitrobenzene were obtained using the Sub 1-III-A1-1 synthesis method to obtain 42.43 g (yield: 70%) of the product.
  • Sub 1-IV-C1-1 (35.84g, 76.4mmol) obtained in the above synthesis in 1,3-dibromobenzene (27.02g, 114.5mmol), Pd (PPh 3 ) 4 (4.41g, 3.8mmol), K 2 CO 3 (31.66 g, 229.1 mmol), THF, and water were obtained using the Sub 1-V-A1-1 synthesis method to obtain 27.78 g (yield: 73%) of product.
  • Sub 1-VI-C1-1 (23.71 g, 43.5 mmol) obtained in the above synthesis was subjected to 1-bromo-4-iodobenzene (18.44 g, 65.2 mmol), Pd (PPh 3 ) 4 (2.51 g, 2.2 mmol), K 2 CO 3 (18.02 g, 130.4 mmol), THF, and water were obtained using the Sub 1-A1-1 synthesis method to obtain 20.23 g (yield: 81%) of the product.
  • Naphthalen-1-ylboronic acid (73.6g, 427.9mmol) as starting material, 1,4-dibromo-2-nitrobenzene (180.31g, 641.9mmol), Pd (PPh 3 ) 4 (24.73g, 21.4mmol), K 2 CO 3 (177.43 g, 1283.8 mmol), THF, and water were obtained using the Sub 1-I-A1-1 synthesis method to obtain 68.81 g (yield: 49%) of the product.
  • Sub 1-II-A2-1 (44.09g, 148.9mmol) obtained in the above synthesis to iodobenzene (45.56g, 223.3mmol), Na 2 SO 4 (21.15g, 148.9mmol), K 2 CO 3 (20.58g, 148.9 mmol), Cu (2.84 g, 44.7 mmol) and nitrobenzene were obtained using the Sub 1-III-A1-1 synthesis method to obtain 41.01 g (yield: 74%) of the product.
  • Sub 1-III-A2-1 (41.01 g, 110.2 mmol) obtained in the above synthesis to Bis (pinacolato) diboron (30.77 g, 121.2 mmol), Pd (dppf) Cl 2 (2.7 g, 3.3 mmol), KOAc (32.43) g, 330.5 mmol), and DMF were used to obtain 36.96 g (yield: 80%) of the product using the Sub 1-IV-A1-1 synthesis method.
  • Sub 1-IV-A2-1 (36.96g, 88.1mmol) obtained in the above synthesis of 1,3-dibromobenzene (31.19g, 132.2mmol), Pd (PPh 3 ) 4 (5.09g, 4.4mmol), K 2 CO 3 (36.55 g, 264.4 mmol), THF, and water were obtained using the Sub 1-V-A1-1 synthesis method to obtain 30.43 g (yield: 77%) of the product.
  • Sub 1-V-A2-1 (30.43g, 67.9mmol) obtained in the above synthesis to Bis (pinacolato) diboron (18.96g, 74.7mmol), Pd (dppf) Cl 2 (1.66g, 2.0mmol), KOAc (19.98) g, 203.6 mmol), and DMF were used to obtain 26.9 g (yield: 80%) of the product using the Sub 1-VI-A1-1 synthesis method.
  • Sub 1-VI-A2-1 (26.9g, 54.3mmol) obtained in the above synthesis was subjected to 1-bromo-4-iodobenzene (23.04g, 81.4mmol), Pd (PPh 3 ) 4 (3.14g, 2.7mmol), K 2 CO 3 (22.51 g, 162.9 mmol), THF, and water were obtained using the Sub 1-A1-1 synthesis method to obtain 25.06 g (yield: 88%) of the product.
  • Sub 1-VI-A1-1 (26.9 g, 54.3 mmol) obtained in the above synthesis was prepared with 1-bromo-3-iodobenzene (23.04 g, 81.4 mmol), Pd (PPh 3 ) 4 (3.14 g, 2.7 mmol), K 2 CO 3 (22.51 g, 162.9 mmol), THF, and water were obtained using the Sub 1-A1-1 synthesis method to obtain 23.6 g (yield: 83%) of the product.
  • Sub 1-VI-C1-1 (29.6g, 54.3mmol) obtained in the above synthesis was subjected to 1-bromo-2-iodobenzene (23.04g, 81.4mmol), Pd (PPh 3 ) 4 (3.14g, 2.7mmol), K 2 CO 3 (22.51 g, 162.9 mmol), THF, and water were obtained using the Sub 1-A1-1 synthesis method to obtain 25.3 g (yield: 81%) of the product.
  • Sub 1-VI-A2-1 (26.9g, 54.3mmol) obtained in the above synthesis was subjected to 1-bromo-2-iodobenzene (23.04g, 81.4mmol), Pd (PPh 3 ) 4 (3.14g, 2.7mmol), K 2 CO 3 (22.51 g, 162.9 mmol), THF, and water were obtained using the Sub 1-A1-1 synthesis method to obtain 21.4 g (yield: 75%) of the product.
  • Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 11, but is not limited thereto.
  • bromobenzene (30.47g, 194.1mmol), 4-fluoroaniline (43.13g, 388.1mmol), Pd 2 (dba) 3 (5.33g, 5.8mmol), 50% P ( t -Bu) 3 (7.6ml, 15.5 mmol), NaO t -Bu (55.95 g, 582.2 mmol) and toluene were obtained using the Sub 2-1 synthesis method to obtain 29.79 g (yield: 82%) of the product.
  • Sub 2-3 (7.41 g, 25.5 mmol) obtained in the above synthesis was dissolved in toluene in a round bottom flask, and then Sub 1-A1-1 (16.06 g, 30.6 mmol), Pd 2 (dba) 3 (0.7 g, 0.8 mmol), 50% P ( t -Bu) 3 (1 ml, 2 mmol), NaO t -Bu (7.36 g, 76.5 mmol) was added and stirred at 100 ° C.
  • Sub 2-8 (8.96 g, 18.5 mmol) obtained in the above synthesis to Sub 1-A1-1 (11.61 g, 22.1 mmol), Pd 2 (dba) 3 (0.51 g, 0.6 mmol), 50% P ( t ⁇ Bu) 3 (0.7 ml, 1.5 mmol), NaO t -Bu (5.32 g, 55.4 mmol) and toluene were obtained using the Product A1-1 synthesis to obtain 12.17 g (yield: 71%) of the product.
  • Sub 2-17 (6.07 g, 18.9 mmol) obtained in the above synthesis to Sub 1-A1-2 (13.61 g, 22.7 mmol), Pd 2 (dba) 3 (0.52 g, 0.6 mmol), 50% P ( t ⁇ Bu) 3 (0.7 ml, 1.5 mmol), NaO t -Bu (5.45 g, 56.7 mmol) and toluene were obtained using the Product A1-1 synthesis to obtain 11.91 g (yield: 75%) of the product.
  • Sub 2-6 (6.32 g, 18.8 mmol) obtained in the above synthesis in Sub 1-A1-5 (11.88 g, 22.6 mmol), Pd 2 (dba) 3 (0.52 g, 0.6 mmol), 50% P ( t ⁇ Bu) 3 (0.7 ml, 1.5 mmol), NaO t -Bu (5.43 g, 56.5 mmol) and toluene were obtained using the Product A1-1 synthesis to obtain 10.29 g (yield: 70%) of the product.
  • Sub 2-7 (7.49 g, 18.3 mmol) obtained in the above synthesis to Sub 1-C2-1 (12.61 g, 21.9 mmol), Pd 2 (dba) 3 (0.5 g, 0.5 mmol), 50% P ( t ⁇ Bu) 3 (0.7 ml, 1.5 mmol), NaO t -Bu (5.27 g, 54.9 mmol) and toluene were obtained using the Product A1-1 synthesis method to obtain 11.23 g (yield: 68%) of the product.
  • Sub 2-8 (8.9 g, 18.3 mmol) obtained in the above synthesis to Sub 1-V-A1-1 (Sub 1-A7-1) (9.8 g, 21.9 mmol), Pd 2 (dba) 3 (0.5 g, 0.5 mmol), 50% P ( t -Bu) 3 (0.7 ml, 1.5 mmol), NaO t -Bu (5.27 g, 54.9 mmol) and toluene were obtained using the Product A1-1 synthesis method. 74%).
  • Sub 2-8 (4.5 g, 18.3 mmol) obtained in the above synthesis to Sub 1-V-A1-1 (Sub 1-A7-1) (10.9 g, 21.9 mmol), Pd 2 (dba) 3 (0.5 g, 0.5 mmol), 50% P ( t -Bu) 3 (0.7 ml, 1.5 mmol), NaO t -Bu (5.27 g, 54.9 mmol) and toluene were obtained using 8.5 A of the product A1-1 synthesis (yield: 70%).
  • An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as a hole transport layer material.
  • -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 vacuum deposition of the compound of the present invention to the hole injection layer at a thickness of 60 nm. To form a hole transport layer.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • Ir (ppy) 3 tris (2-phenylpyridine) -iridium
  • BAlq (1,1'-bisphenyl) -4-oleito) bis (2-methyl-8-quinolinoleito) 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, an alkali metal halide, was deposited to a thickness of 0.2 nm 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
  • the organic electric device manufactured according to [Experimental Example I] is shown as Experimental Example (1) to Experimental Example (120) in Table 12 below.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example I, except that Comparative Compound A was used as the hole transport layer.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example I, except that Comparative Compound B was used as the hole transport layer.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example I, except that Comparative Compound C was used as the hole transport layer.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example I, except that Comparative Compound D was used as the hole transport layer.
  • the forward bias DC voltage was applied to the organic electroluminescent devices according to Experimental Example I (Experimental Example (1) to Experimental Example 120) 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 the life measurement equipment manufactured by McScience Inc. at a luminance of 5000 cd / m 2.
  • Table 12 shows the fabrication of devices for Experimental Example I (Experimental Example (1) to Experimental Example 120) and Comparative Example I (Comparative Example (1) to Comparative Example (4)) applying the compound according to the present invention and its The evaluation result is shown.
  • the organic electroluminescent device using the compound of the present invention as a hole transport layer material has a significantly improved luminous efficiency and lifetime compared to the organic electroluminescent devices of Comparative Examples (1) to (4).
  • the compound of the present invention in which the non-linear linking group L is substituted with the comparative compound A, which is NPB, and the linking group L is connected in a para-position (linear), and the comparative compound B, the comparative compound C, and the comparative compound D are linear. This excellent device result is shown.
  • Nonlinear compounds have a shorter conjugation length than linear compounds, resulting in wider band gaps, deeper HOMO energy levels and higher T1 values. Therefore, due to the deep HOMO energy level, holes are smoothly transported to the light emitting layer, and the ability to block electrons with a high T1 value is improved, so that excitons are more easily generated in the light emitting layer, thereby improving efficiency and lifespan.
  • An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as a light emitting auxiliary layer material.
  • a hole injection layer is formed by vacuum depositing 2-TNATA with a thickness of 60 nm on an ITO layer (anode) formed on an organic substrate, and then 4,4-bis [N- (1-naphthyl) on the hole injection layer. ) -N-phenylamino] biphenyl (abbreviated as "NPD”) was vacuum deposited to a thickness of 60 nm to form a hole transport layer.
  • a compound of the present invention was vacuum-deposited on the hole transport layer to form a light emitting auxiliary layer by vacuum deposition at a thickness of 20 nm, and then, CBP was used as a host on the light emitting auxiliary layer, and bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate ( Hereafter, abbreviated as "(piq) 2 Ir (acac)" as a dopant, the mixture doped at 95: 5 weight 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 an alkali metal halide
  • Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.
  • the organic electric device manufactured according to [Experimental Example II] is shown as Experimental Example (121) to Experimental Example (240) in Table 13 below.
  • 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 A was used as the light emitting auxiliary layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example II, except that Comparative Compound B was used as the light emitting auxiliary layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example II, except that Comparative Compound C was used as the light emitting auxiliary layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example II, except that Comparative Compound D was used as the light emitting auxiliary layer material.
  • the forward bias DC voltage was applied to the organic electroluminescent devices according to Experimental Example II (Experimental Example 121 to 240) and Comparative Example II (Comparative Example (5) to Comparative Example (9)) prepared as described above.
  • the electroluminescence (EL) characteristics were measured by the PR-650 photoresearch company, and the T95 life was measured using a life-time measurement device manufactured by McScience Inc. at a luminance of 2500 cd / m 2.
  • Table 13 shows the fabrication of devices for Experimental Example II (Experimental Example (121) to Experimental Example 240) and Comparative Example II (Comparative Example (5) to Comparative Example (9)) to which the compound according to the present invention is applied and its The evaluation result is shown.
  • An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as a light emitting auxiliary layer material.
  • a hole injection layer was formed by vacuum depositing 2-TNATA with a thickness of 60 nm on an ITO layer (anode) formed on an organic substrate, and then a hole transport layer was formed by vacuum depositing NPD with a thickness of 60 nm on the hole injection layer.
  • a compound of the present invention was vacuum-deposited on the hole transport layer to form a light emitting auxiliary layer by vacuum deposition at a thickness of 20 nm, and then 95: 5 weight by using CBP as a host and Ir (ppy) 3 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 an alkali metal halide
  • LiF was deposited to a thickness of 0.2 nm to form an electron injection layer
  • an Al was deposited to a thickness of 150 nm to form a cathode, thereby manufacturing an organic electroluminescent device.
  • the organic electric device manufactured according to [Experimental Example III] is shown as Experimental Example (241) to Experimental Example (360) in Table 14 below.
  • 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 A was used as the light emitting auxiliary layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example III, except that Comparative Compound B was used as the 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 as the 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 as the light emitting auxiliary layer material.
  • the forward bias DC voltage was applied to the organic electroluminescent devices according to Experimental Example III (Experimental Example 241 to 360) and Comparative Example III (Comparative Example 10 to Comparative Example 14) prepared as described above.
  • the electroluminescence (EL) characteristics were measured with a PR-650 photoresearch company, and the T95 life was measured using the life measurement equipment manufactured by McScience Inc. at a luminance of 5000 cd / m 2.
  • Table 14 shows the fabrication of devices for Experimental Example III (Experimental Example 241 to Experimental Example 360) and Comparative Example III (Comparative Example (10) to Comparative Example (14)) to which the compound according to the present invention was applied. The evaluation result is shown.
  • An organic electroluminescent device was manufactured according to a conventional method using the compound of the present invention as a light emitting auxiliary layer material.
  • a hole injection layer was formed by vacuum depositing 2-TNATA with a thickness of 60 nm on an ITO layer (anode) formed on an organic substrate, and then a hole transport layer was formed by vacuum depositing NPD with a thickness of 60 nm on the hole injection layer.
  • a compound of the present invention was vacuum-deposited on the hole transport layer to form a light emitting auxiliary layer by vacuum deposition at a thickness of 20 nm, and 9, 10-di (naphthalen-2-yl) anthracene was used as a host on the light emitting auxiliary layer.
  • a light emitting layer was formed by vacuum depositing a mixture doped at 93: 7 weight using -052X (manufactured by Idemitsu kosan) as a dopant at a thickness of 30 nm. Subsequently, 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 an alkali metal halide
  • the organic electric device manufactured according to [Experimental Example IV] is shown as Experimental Example (361) to Experimental Example (480) in Table 15 below.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example IV, except that no light emitting auxiliary layer was formed.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example IV, except that Comparative Compound A was used as the light emitting auxiliary layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example IV, except that Comparative Compound B was used as the light emitting auxiliary layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example IV, except that Comparative Compound C was used as the light emitting auxiliary layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Experimental Example IV, except that Comparative Compound D was used as the light emitting auxiliary layer material.
  • the forward bias DC voltage was applied to the organic electroluminescent devices of Experimental Example IV (Experimental Example 361 to 480) and Comparative Example IV (Comparative Example 15 to Comparative Example 19) 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 500 cd / m 2.
  • Table 15 shows the fabrication of devices for Experimental Example IV (Experimental Example (361) to Experimental Example (480)) and Comparative Example IV (Comparative Example (15) to Comparative Example (19)) to which the compound according to the present invention was applied and its The evaluation result is shown.
  • the organic electroluminescent device using the compound of the present invention as the light emitting auxiliary layer material is compared with the organic electroluminescent device of Comparative Examples (5) to (19) and It can be seen that the service life is significantly improved.
  • the connector is connected non-linearly to have a deep HOMO energy level and a high T1 value, thereby improving the ability to transport holes to the light emitting layer smoothly and to block electrons, thereby improving efficiency and lifespan. It is believed that this is improved.

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Abstract

Cette invention concerne un nouveau composé capable d'améliorer le rendement électroluminescent, la stabilité, et la durée de vie d'un élément, un élément électronique organique l'utilisant, et un dispositif électronique associé.
PCT/KR2013/010220 2012-11-13 2013-11-12 Composé pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique associé WO2014077558A1 (fr)

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US10777747B2 (en) 2016-12-05 2020-09-15 Samsung Display Co., Ltd. Amine compound and organic electroluminescence device including the same
US11165029B2 (en) 2016-09-22 2021-11-02 Samsung Display Co., Ltd. Amine compound and organic electroluminescence device including the same
EP4089073A1 (fr) * 2021-05-12 2022-11-16 Samsung Display Co., Ltd. Dispositif luminescent et composé contenant de l'azote pour un dispositif de luminescence

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US20160365517A1 (en) * 2014-02-27 2016-12-15 Duk San Neolux Co., Ltd. Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof
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CN107667098A (zh) * 2015-05-27 2018-02-06 德山新勒克斯有限公司 有机电气元件用化合物、利用其的有机电气元件及其电子装置
US11380846B2 (en) 2015-05-27 2022-07-05 Duk San Neolux Co., Ltd. Compound for organic electric element, organic electric element comprising the same and electronic device thereof
CN107667098B (zh) * 2015-05-27 2024-04-16 德山新勒克斯有限公司 有机电气元件用化合物、利用其的有机电气元件及其电子装置
US20160351819A1 (en) * 2015-06-01 2016-12-01 Samsung Display Co., Ltd. Organic light emitting diode and organic light emitting diode display including the same
US11165029B2 (en) 2016-09-22 2021-11-02 Samsung Display Co., Ltd. Amine compound and organic electroluminescence device including the same
US10777747B2 (en) 2016-12-05 2020-09-15 Samsung Display Co., Ltd. Amine compound and organic electroluminescence device including the same
EP4089073A1 (fr) * 2021-05-12 2022-11-16 Samsung Display Co., Ltd. Dispositif luminescent et composé contenant de l'azote pour un dispositif de luminescence

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