WO2015064969A2 - Composé pour dispositif électroluminescent organique, dispositif électroluminescent organique le contenant, et dispositif électronique dans lequel est employé ledit dispositif électroluminescent organique - Google Patents

Composé pour dispositif électroluminescent organique, dispositif électroluminescent organique le contenant, et dispositif électronique dans lequel est employé ledit dispositif électroluminescent organique Download PDF

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WO2015064969A2
WO2015064969A2 PCT/KR2014/010081 KR2014010081W WO2015064969A2 WO 2015064969 A2 WO2015064969 A2 WO 2015064969A2 KR 2014010081 W KR2014010081 W KR 2014010081W WO 2015064969 A2 WO2015064969 A2 WO 2015064969A2
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organic
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layer
electrode
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WO2015064969A3 (fr
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박정근
이선희
박형근
조혜민
이대원
박성제
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덕산네오룩스 주식회사
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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    • 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
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
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    • 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
    • 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
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    • 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
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • 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
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1416—Condensed systems
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often formed of a multi-layered 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 device may be classified into a hole injection material, a hole transport material, a light emitting 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.As the efficiency increases, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic materials due to Jouleheating generated during driving decreases, resulting in a lifetime. This tends to be higher. However, simply improving the organic layer may not maximize the efficiency. Because of the optimal combination of energy level, T 1 value, and intrinsic properties (mobility, interfacial properties, etc.) between organic layers, long life and high efficiency can be achieved simultaneously. Because.
  • 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 present invention provides a compound having high electron mobility and high temperature stability, and having a more efficient hole blocking ability at a high T 1 value, and at the same time, using the compound to improve efficiency, lifetime and color purity. And to provide an electronic device comprising the same.
  • 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.
  • a compound having high electron mobility and high temperature stability and having a more efficient hole blocking ability with a high T 1 value can be provided, and the compound can be used to improve efficiency, lifetime and color purity of the device. Can be improved.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to the present invention.
  • halo or halogen as used herein is fluorine (F), bromine (Br), chlorine (Cl) or iodine (I) unless otherwise indicated.
  • alkyl or “alkyl group” has a single bond of 1 to 60 carbon atoms, unless otherwise indicated, and is a straight chain alkyl group, branched chain alkyl group, cycloalkyl (alicyclic) group, alkyl-substituted cyclo Radicals of saturated aliphatic functional groups, including alkyl groups, cycloalkyl-substituted alkyl groups.
  • heteroalkyl group means that at least one of the carbon atoms constituting the alkyl group has been replaced with a heteroatom.
  • alkenyl group or “alkynyl group”, unless stated otherwise, has a double or triple bond of 2 to 60 carbon atoms, and includes a straight or branched chain group, and is not limited thereto. It is not.
  • cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
  • alkoxyl group means an alkyl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 1 to 60, and is limited herein. It is not.
  • alkenoxyl group means an alkenyl group to which an oxygen radical is attached, and unless otherwise stated, it is 2 to 60 It has carbon number of, It is not limited to this.
  • aryloxyl group or “aryloxy group” means an aryl group to which an oxygen radical is attached, and unless otherwise specified, has a carbon number of 6 to 60, but is not limited thereto.
  • aryl group and “arylene group” have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
  • an aryl group or an arylene group means an aromatic of a single ring or multiple rings, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction.
  • the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.
  • aryl or "ar” means a radical substituted with an aryl group.
  • an arylalkyl group is an alkyl group substituted with an aryl group
  • an arylalkenyl group is an alkenyl group substituted with an aryl group
  • the radical substituted with an aryl group has the carbon number described herein.
  • an arylalkoxy group means an alkoxy group substituted with an aryl group
  • an alkoxylcarbonyl group means a carbonyl group substituted with an alkoxyl group
  • an arylcarbonylalkenyl group means an alkenyl group substituted with an arylcarbonyl group.
  • the arylcarbonyl group is a carbonyl group substituted with an aryl group.
  • heteroalkyl means an alkyl including one or more heteroatoms unless otherwise indicated.
  • heteroaryl group or “heteroarylene group” means an aryl group or arylene group having 2 to 60 carbon atoms, each containing one or more heteroatoms, unless otherwise specified. It may include at least one of a single ring and multiple rings, and may be formed by combining adjacent functional groups.
  • heterocyclic group includes one or more heteroatoms, unless otherwise indicated, and has from 2 to 60 carbon atoms, and includes at least one of single and multiple rings, heteroaliphatic rings and hetero Aromatic rings. Adjacent functional groups may be formed in combination.
  • heteroatom refers to N, O, S, P or Si unless otherwise stated.
  • Heterocyclic groups may also include rings comprising SO 2 in place of the carbon forming the ring.
  • a “heterocyclic group” includes the following compounds.
  • aliphatic as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms
  • aliphatic ring means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
  • ring refers to a fused ring consisting of an aliphatic ring having 3 to 60 carbon atoms, an aromatic ring having 6 to 60 carbon atoms, a hetero ring having 2 to 60 carbon atoms, or a combination thereof. Saturated or unsaturated rings.
  • heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.
  • carbonyl used in the present invention is represented by -COR ', wherein R' is hydrogen, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, and 3 to 30 carbon atoms. Cycloalkyl group, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, or a combination thereof.
  • ether as used herein is represented by -RO-R ', wherein R or R' are each independently of each other hydrogen, an alkyl group having 1 to 20 carbon atoms, It is an aryl group, a C3-C30 cycloalkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, or a combination thereof.
  • substituted in the term “substituted or unsubstituted” as used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, C 1 ⁇ C 20 alkoxyl group, C 1 ⁇ C 20 alkylamine group, C 1 ⁇ C 20 alkylthiophene group, C 6 ⁇ C 20 arylthiophene group, C 2 ⁇ C 20 alkenyl group, C 2 ⁇ C 20 alkynyl, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 20 aryl group, of a C 6 ⁇ C 20 substituted by deuterium aryl group, a C 8 ⁇ C 20 aryl alkenyl group, a silane group, a boron Group, germanium group, and C 2 ⁇ C 20 It is meant to be substituted with one or more substituents selected from the group consist
  • the substituent R 1 when a is an integer of 0, the substituent R 1 is absent, when a is an integer of 1, one substituent R 1 is bonded to any one of carbons forming the benzene ring, and a is an integer of 2 or 3 are each bonded as follows, where R 1 may be the same or different from each other, and when a is an integer from 4 to 6, it is bonded to the carbon of the benzene ring in a similar manner, while the indication of hydrogen bonded to the carbon forming the benzene ring Is omitted.
  • FIG. 1 is an exemplary view of an organic electric device according to an embodiment of the present invention.
  • the organic electric device 100 includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110.
  • the first electrode 120 may be an anode (anode)
  • the second electrode 180 may be a cathode (cathode)
  • the first electrode may be a cathode and the second electrode may be an anode.
  • the organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence. At this time, the remaining layers except for the light emitting layer 150 may not be formed.
  • the hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.
  • the organic electric device according to the present invention may further include a protective layer or a light efficiency improving layer (Capping layer) formed on one surface of the at least one surface of the first electrode and the second electrode opposite to the organic material layer.
  • a protective layer or a light efficiency improving layer Capping layer
  • the compound according to the present invention applied to the organic material layer of the hole injection layer 130, the hole transport layer 140, the electron transport layer 160, the electron injection layer 170, the host of the dopant or light efficiency improvement layer of the light emitting layer 150 Can be used as a material.
  • the organic electroluminescent device may be manufactured using a PVD method.
  • the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer are formed thereon.
  • the organic material layer including the 160 and the electron injection layer 170 it can be prepared by depositing a material that can be used as the cathode 180 thereon.
  • the organic material layer is a solution or solvent process (e.g., spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blading) using various polymer materials. It can be produced in fewer layers by methods such as ding process, screen printing process, or thermal transfer method. Since the organic material layer according to the present invention may be formed in various ways, the scope of the present invention is not limited by the forming method.
  • the organic electric element according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • WOLED White Organic Light Emitting Device
  • Various structures for white organic light emitting devices mainly used as backlight devices have been proposed and patented. Representatively, a side-by-side method in which R (Red), G (Green), and B (Blue) light emitting parts are mutually planarized, and a stacking method in which R, G, and B light emitting layers are stacked up and down. And a color conversion material (CCM) method using photo-luminescence of an inorganic phosphor by using electroluminescence by a blue (B) organic light emitting layer and light therefrom. May also be applied to these WOLEDs.
  • CCM color conversion material
  • the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device.
  • OLED organic electroluminescent device
  • OPC organic photoconductor
  • organic TFT organic transistor
  • Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device.
  • the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
  • the compound according to one aspect of the present invention is represented by the following formula (1).
  • L 1 and L 2 are each independently a single bond, an arylene group or a fluorenylene group of C 6 to C 60 .
  • L 1 and L 2 may be independently of each other phenyl, biphenyl, naphthyl and the like.
  • R 3 and R 4 are independently of each other a C 6 ⁇ C 60 aryl group.
  • R 3 and R 4 can be phenyl, biphenyl, naphthyl, perylene and the like.
  • R 1 and R 2 are independently selected from the following group. However, when L 1 and L 2 are a single bond, pyridine is excluded from R 1 and R 2 .
  • R in the group is deuterium; halogen; C 1 ⁇ C 50 Alkyl group; C 6 ⁇ C 60 Aryl group; And a C 2 -C 60 heterocyclic group including at least one heteroatom of O, N, S, Si, and P, n is an integer of 0 to 4, and m is 0 to 6 Is an integer, and l is an integer of 0-5.
  • the arylene group, fluorenylene group, aryl group, heterocyclic group are each deuterium; halogen; Silane group; Siloxane groups; Boron group; Germanium group; Cyano group; Nitro group; -LN (R a ) (R b ); C 1 ⁇ C 20 of the import alkylthio; C 1 -C 20 alkoxyl group; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 Alkenyl group; Alkynyl groups of C 2 to C 20 ; Of C 6 ⁇ C 20 Aryl group; C 6 ⁇ C 20 aryl group substituted with deuterium; Fluorenyl group; C 2 ⁇ C 20 heterocyclic group; C 3 -C 20 cycloalkyl group; It may be substituted with one or more substituents selected from the group consisting of C 7 ⁇ C 20 arylalkyl group and C 8 ⁇ C 20 arylalkenyl group.
  • L is 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 C 2 ⁇ C 60 Heterocyclic group; It is selected from the group consisting of, R a and R b are independently of each other C 6 ⁇ C 60 An 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.
  • Formula 1 may be represented by any one of the following Formulas 2-7.
  • L 1 , L 2 , R 3 , R 4 , R, n and m and the like may be defined as defined in formula (1).
  • Formula 1 to Formula 7 may be one of the following compounds.
  • the present invention provides a compound for an organic electric device represented by Chemical Formula 1.
  • the present invention provides an organic electric device containing the compound represented by the formula (1).
  • the organic electric element includes a first electrode; Second electrode; And an organic material layer positioned between the first electrode and the second electrode.
  • the organic material layer may include a compound represented by Chemical Formula 1, and Chemical Formula 1 may be included in the electron transport layer of the organic material layer. That is, the compound represented by Formula 1 may be used as the electron transport layer material.
  • the present invention provides an organic electroluminescent device comprising a compound represented by the respective formula in the organic material layer To provide.
  • the present invention may include at least a light emitting auxiliary layer in the organic material layer.
  • the present invention provides 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. It provides an organic electric element further comprising.
  • the present invention provides 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. It provides an organic electric element further comprising.
  • the present invention provides an organic electroluminescent device is formed by any one of the organic coating layer, 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 a display device including an organic electric element including 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.
  • the compound represented by Chemical Formula 1 according to the present invention is prepared by reacting Sub 1 and Sub 2 as in Scheme 1 below, but is not limited thereto.
  • the compound according to the present invention may be prepared by reacting Sub 1 and Sub 2 as in Scheme 1 below.
  • Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below.
  • Sub 1-3 (1 equiv), Sub 1-4 (1 equiv), Pd (PPh 3 ) 4 (0.03 equiv) and K 2 CO 3 (3 equiv) are dissolved in anhydrous THF and a small amount of water, followed by 24 It was refluxed for hours. After the reaction was completed, the temperature of the reactant was cooled to room temperature, extracted with CH 2 Cl 2 , and washed with water. After removal of a small amount of water with anhydrous MgSO 4 and filtration under reduced pressure, the product produced by concentration of the organic solvent was separated by a silicagel column to obtain the desired Sub 1-5.
  • Sub 1 is not limited to the following compounds, but may be the following compounds, the following compounds may be synthesized using the reaction mechanism used in the reaction. On the other hand, FD-MS values for the following compounds are shown in Table 1.
  • CBP 4,4'-N, N'-dicarbazole-biphenyl
  • Ir (ppy) 3 tris (2-phenylpyridine) -iridium
  • BAlq (1,1 'bisphenyl) -4-oleito) bis (2-methyl-8-quinoline oleito) aluminum
  • a layer was formed, and the compound (1-1) of the present invention was vacuum deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Thereafter, LiF, which is a halogenated alkali metal, was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and then an Al was deposited to a thickness of 150 nm to form an organic electroluminescent device.
  • LiF which is a halogenated alkali metal
  • An organic electroluminescent device was manufactured according to the same method as Example 1 except for using the compounds 1-2 to 7-8 of the present invention shown in Table 4 instead of the compound 1-1 of the present invention as an electron transport layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example I, except that Comparative Compound 1 was used instead of the compound according to the present invention as an electron transport layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example I, except that Comparative Compound 2 was used instead of the compound according to the present invention as an electron transport layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example I, except that Comparative Compound 3 was used instead of the compound according to the present invention as an electron transport layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example I, except that Comparative Compound 4 was used instead of the compound according to the present invention as an electron transport layer material.
  • the organic electroluminescent device (OLED) using the compounds of the present invention is used as an electron transport layer material, the driving voltage and high efficiency and high lifespan than the comparative compound 1 of Alq 3 widely used conventionally Indicated.
  • the dopant T 1 value (2.0 eV) of the Alq 3 is significantly lower T 1 values using as an electron transporting layer than the Ir (ppy) 3 of the T 1 value (2.4 eV) used in the light emitting layer invention, It exhibits a T 1 value (2.5 ev to 2.6 ev) that is generally higher than the T 1 value of Ir (ppy) 3 (2.4 eV), thereby improving hole blocking ability as well as excitons in the light emitting layer. This is because the relative probability of staying well increases.
  • the device characteristics were described in terms of the light emitting layer (phosphorescent host).
  • an organic material layer of the organic electric element such as a light emitting auxiliary layer, it can be used in a single or mixed with other materials. Therefore, the above-described compounds of the present invention may be used in combination with a single or other material in addition to the light emitting layer (phosphorescent host), for example, an organic material layer, for example, an electron transport layer, an electron injection layer, a hole injection layer, a hole transport layer, a light emitting auxiliary layer, and the like. .

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  • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Cette invention concerne un nouveau composé capable d'améliorer le rendement lumineux, la stabilité, et la longévité d'un dispositif. L'invention concerne également un dispositif électronique organique comprenant ce composé et un dispositif électronique dans lequel est employé ledit dispositif électroluminescent organique.
PCT/KR2014/010081 2013-10-29 2014-10-24 Composé pour dispositif électroluminescent organique, dispositif électroluminescent organique le contenant, et dispositif électronique dans lequel est employé ledit dispositif électroluminescent organique WO2015064969A2 (fr)

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KR1020130128911A KR102172735B1 (ko) 2013-10-29 2013-10-29 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치

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CN109912593A (zh) * 2017-12-13 2019-06-21 乐金显示有限公司 有机化合物、包含该化合物的有机发光二极管和有机发光显示器
CN110183441A (zh) * 2019-05-09 2019-08-30 江苏医药职业学院 一种OLED电子传输材料NBphen的制备方法

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WO2010075379A2 (fr) * 2008-12-22 2010-07-01 E. I. Du Pont De Nemours And Company Dispositif électronique comprenant un dérivé de phénanthroline
CN102127073A (zh) * 2010-11-26 2011-07-20 深圳大学 以邻菲罗啉为核心的星状化合物及具该化合物的发光器件
KR20120056000A (ko) * 2010-11-24 2012-06-01 엘지디스플레이 주식회사 전자수송물질 및 이를 이용한 유기전계발광소자
KR20120056418A (ko) * 2010-11-25 2012-06-04 엘지디스플레이 주식회사 전자수송물질 및 이를 이용한 유기전계발광소자

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KR100958641B1 (ko) * 2008-08-18 2010-05-20 삼성모바일디스플레이주식회사 광효율 개선층을 구비한 유기 발광 소자

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WO2010075379A2 (fr) * 2008-12-22 2010-07-01 E. I. Du Pont De Nemours And Company Dispositif électronique comprenant un dérivé de phénanthroline
KR20120056000A (ko) * 2010-11-24 2012-06-01 엘지디스플레이 주식회사 전자수송물질 및 이를 이용한 유기전계발광소자
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109912593A (zh) * 2017-12-13 2019-06-21 乐金显示有限公司 有机化合物、包含该化合物的有机发光二极管和有机发光显示器
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CN110183441A (zh) * 2019-05-09 2019-08-30 江苏医药职业学院 一种OLED电子传输材料NBphen的制备方法
CN110183441B (zh) * 2019-05-09 2020-08-14 江苏医药职业学院 一种OLED电子传输材料NBphen的制备方法

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