WO2019022435A1 - Composé pour dispositif électronique organique, dispositif électronique organique l'utilisant et appareil électronique associé - Google Patents

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

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WO2019022435A1
WO2019022435A1 PCT/KR2018/008146 KR2018008146W WO2019022435A1 WO 2019022435 A1 WO2019022435 A1 WO 2019022435A1 KR 2018008146 W KR2018008146 W KR 2018008146W WO 2019022435 A1 WO2019022435 A1 WO 2019022435A1
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장재완
이윤석
박정환
박치현
이선희
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DukSan Neolux Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/16—Peri-condensed systems
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    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/06—Peri-condensed systems
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/14—Ortho-condensed systems
    • C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/16—Peri-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/16—Peri-condensed systems
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    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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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
    • H10K85/657—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
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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
    • H10K85/657—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
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • 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
    • H10K59/10—OLED displays
    • 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 therefor.
  • organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.
  • An organic electric device using an organic light emitting phenomenon generally has a structure including an anode, an anode, and an organic material layer therebetween.
  • the organic material layer is often formed of a multi-layered structure made of different materials, and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • a material used as an organic material layer in an organic electric device may be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.
  • the efficiency, lifetime, and driving voltage are related to each other. As the efficiency increases, the driving voltage drops and the driving voltage drops. As a result, crystallization of the organic material due to Joule heating, which occurs during driving, And the lifetime tends to increase. However, simply improving the organic material layer can not maximize the efficiency. This is because, when the optimal combination of the energy level and T1 value between each organic material layer and the intrinsic properties (mobility, interface characteristics, etc.) of the material are achieved, long life and high efficiency can be achieved at the same time.
  • 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 for the hole transport layer has a low HOMO value and therefore has a low T 1 value.
  • the exciton generated in the light emitting layer is transferred to the interface of the hole transport layer or the hole transport layer, Resulting in light emission at the interface or charge unbalance in the light emitting layer, resulting in light emission at the interface of the hole transporting layer.
  • the color purity and efficiency of the organic electronic device are lowered and the lifetime is shortened. Therefore, it should be a material having a HOMO level between the HOMO energy level of the hole transporting layer and the HOMO energy level of the light emitting layer, and has a high T1 value and a hole mobility (within a driving voltage range of a full device blue device) mobility of the light-emitting layer.
  • a light emitting layer and a light emitting auxiliary layer material having stable characteristics that is, a high glass transition temperature, against joule heating generated when a device is driven.
  • the low glass transition temperature of the light emitting layer and the light emitting auxiliary layer material lowers the uniformity of the surface of the thin film during device operation, and the material may be deformed due to heat generated when the device is driven.
  • OLED devices are mainly formed by a deposition method, and it is necessary to develop a material that can withstand a long period of time, that is, a material having high heat resistance characteristics.
  • a material constituting the organic material layer in the device for example, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material,
  • a material constituting the organic material layer in the device for example, a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material.
  • the development of a stable and efficient organic material layer for an organic electric device has not been sufficiently developed yet. Accordingly, development of new materials is continuously required, and development of a material used for a light-emission-assisting layer, a light-emitting layer, and the like is urgently required.
  • An object of the present invention is to provide a compound capable of lowering the driving voltage of a device and improving the luminous efficiency, color purity and lifetime of the device, an organic electric device using the same, and an electronic device therefor.
  • the invention provides compounds represented by the formula:
  • the present invention provides an organic electronic device using the compound represented by the above formula and an electronic device thereof.
  • the compound according to the embodiment of the present invention By using the compound according to the embodiment of the present invention, not only the driving voltage of the device can be lowered, but also the luminous efficiency, color purity and lifetime of the device can be greatly improved.
  • FIG. 1 is an illustration of an organic electroluminescent device according to the present invention.
  • the terms first, second, A, B, (a), (b), and the like can be used. These terms are intended to distinguish the constituent elements from other constituent elements, and the terms do not limit the nature, order or order of the constituent elements.
  • a component is described as being “connected”, “coupled”, or “connected” to another component, the component may be directly connected to or connected to the other component, It should be understood that an element may be “connected,” “coupled,” or “connected.”
  • halo or halogen
  • fluorine F
  • bromine Br
  • chlorine Cl
  • iodine I
  • alkyl or " alkyl group” refers to a straight or branched Quot; means a radical of a saturated aliphatic group, including an alkyl group, a cycloalkyl-substituted alkyl group.
  • haloalkyl group or halogenalkyl group as used in the present invention means an alkyl group substituted with halogen unless otherwise stated.
  • alkenyl group or " alkynyl group”, as used herein, unless otherwise indicated, each have a double bond or triple bond of from 2 to 60 carbon atoms and include straight chain or branched chain groups, It is not.
  • cycloalkyl as used herein, unless otherwise specified, means alkyl which forms a ring having from 3 to 60 carbon atoms, but is not limited thereto.
  • alkoxyl group means an alkyl group to which an oxygen radical is attached and, unless otherwise stated, has a carbon number of 1 to 60, It is not.
  • aryloxyl group or " aryloxy group” refers to an aryl group attached to an oxygen radical and, unless otherwise stated, has a carbon number of 6 to 60, but is not limited thereto.
  • fluorenyl group " or " fluorenylene group " used in the present invention means a monovalent or divalent functional group in which R, R 'and R & Substituted fluorenyl group "or” substituted fluorenylene group "means that at least one of the substituents R, R 'and R” is a substituent other than hydrogen, and R and R' Together with a spy compound.
  • aryl group and arylene group each have 6 to 60 carbon atoms, but are not limited thereto.
  • the aryl group or the arylene group includes a single ring, a ring group, a plurality of ring systems bonded together, a spiro compound and the like.
  • heterocyclic group as used herein includes not only aromatic rings such as “ heteroaryl group” or “ heteroarylene group”, but also nonaromatic rings, Means a ring of 2 to 60 rings, but is not limited thereto.
  • heteroatom as used herein, unless otherwise indicated, refers to N, O, S, P, or Si, wherein the heterocyclic group includes single ring, ring, And the like.
  • heterocyclic group may also include a ring containing SO 2 in place of the carbon forming the ring.
  • heterocyclic group includes the following compounds.
  • ring includes monocyclic and polycyclic rings, including hydrocarbon rings as well as heterocycles containing at least one heteroatom and including aromatic and non-aromatic rings.
  • polycyclic includes ring assemblies such as biphenyl, terphenyl, and the like, as well as various fused ring systems and spiro compounds, including aromatic as well as non-
  • the ring includes, of course, a heterocycle containing at least one heteroatom.
  • ring assemblies means that two or more ring systems (a single ring or a fused ring system) are directly connected to each other through a single bond or a double bond, Means that the number of linkages is one less than the total number of rings in the compound.
  • the ring assemblies may be directly connected to each other through a single bond or a double bond.
  • conjugated ring system refers to a fused ring form shared by at least two atoms, in which the ring system of two or more hydrocarbons is conjugated and contains at least one heteroatom And at least one hetero ring system bonded thereto.
  • conjugated ring systems may be aromatic rings, heteroaromatic rings, aliphatic rings or a combination of these rings.
  • spiro compound used in the present invention has a 'spiro union', and a spiro connection means a connection in which two rings share only one atom.
  • atoms shared in two rings are called 'spyro atoms', and they are referred to as 'monospyros,' 'di spyroses,' and 'tri-spyros', depending on the number of spyro atoms contained in a compound.
  • 'Compounds atoms shared in two rings.
  • substituted is an alkyl group of deuterium, a halogen, an amino group, a nitrile group, a nitro group, C 1 -C 20, C 1 -C 20 alkoxy group, C 1 -C 20 alkyl amine group, C 1 -C 20 alkyl thiophene group, C 6 -C 20 aryl thiophene group, C 2 -C 20 alkenyl, C 2 -C of 20 alkynyl, C 3 -C 20 cycloalkyl group, C 6 -C 20 aryl group, of a C 6 -C 20 aryl group substituted with a heavy hydrogen, C 8 -C 20 aryl alkenyl group, a silane group, a boron And a C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of
  • the 'group name' corresponding to the aryl group, the arylene group, the heterocyclic group and the like exemplified as the examples of the respective symbols and substituents thereof may be described as 'the name of the group reflecting the singer' You may.
  • a monovalent 'group' may be named 'phenanthryl'
  • a bivalent group may be named 'phenanthrylene' It may be described as "phenanthrene" which is the name of the parent compound.
  • pyrimidine it may also be described as 'pyrimidine' irrespective of the valence number, or may be described as the 'name of the group' of the corresponding singer, such as pyrimidine di have.
  • FIG. 1 is an exemplary view of an organic electroluminescent device according to an embodiment of the present invention.
  • an organic electroluminescent device 100 includes a first electrode 120, a second electrode 180 and a first electrode 120 formed on a substrate 110, And an organic material layer containing a compound according to the present invention is provided between the two electrodes 180.
  • the first electrode 120 may be an anode and 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 material layer may include a hole injecting layer 130, a hole transporting layer 140, a light emitting layer 150, an electron transporting layer 160, and an electron injecting layer 170 sequentially on the first electrode 120. At this time, at least one of these layers may be omitted or may further include a hole blocking layer, an electron blocking layer, a light emitting auxiliary layer 151, an electron transporting auxiliary layer, a buffer layer 141, It may also serve as a hole blocking layer.
  • the organic electroluminescent device further includes a protective layer or a light-efficiency-improving layer formed on at least one surface of the first electrode and the second electrode opposite to the organic material layer can do.
  • the compound according to one embodiment of the present invention applied to the organic layer includes a hole injecting layer 130, a hole transporting layer 140, a light emitting auxiliary layer 151, an electron transporting auxiliary layer, an electron transporting layer 160, 170), a host or a dopant material of the light emitting layer 150, or a material of the light efficiency improving layer.
  • the compound of the present invention can be used as a material for the light emitting layer 150, the hole transporting layer 140 and / or the light emitting auxiliary layer 151, and is preferably used as a material for the light emitting auxiliary layer or as a host material for the light emitting layer 150 .
  • the core is the same core, since the band gap, the electrical characteristics, the interface characteristics, and the like can be changed depending on which substituent is bonded at which position, the selection of the core and the combination of the sub- In particular, when the optimal combination of the energy level and T 1 value between the organic layers, and the intrinsic properties (mobility, interface characteristics, etc.) of the materials are achieved, long life and high efficiency can be achieved at the same time.
  • the life and efficiency of the organic electronic device can be improved at the same time.
  • An organic electroluminescent device may be manufactured using various deposition methods. For example, a metal or a metal oxide having conductivity or an alloy thereof may be deposited on a substrate to form a cathode 120, and a hole injection layer 130 may be formed thereon. A hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170, and then depositing a material that can be used as a cathode 180 on the organic layer. have. A light emitting auxiliary layer 151 may be further formed between the hole transporting layer 140 and the light emitting layer 150 and an electron transporting auxiliary layer may be further formed between the light emitting layer 150 and the electron transporting layer 160.
  • the organic material layer may be formed using a variety of polymer materials, not a vapor deposition method, or a solution process or a solvent process such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, It is possible to produce a smaller number of layers by a method such as a dipping process, a screen printing process, or a thermal transfer process. Since the organic material layer according to the present invention can be formed by various methods, the scope of the present invention is not limited by the forming method.
  • the organic electroluminescent device may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.
  • WOLED White Organic Light Emitting Device
  • WOLED has advantages of high resolution realization and fairness, and can be manufactured using existing color filter technology of LCD.
  • Various structures for a white organic light emitting device mainly used as a backlight device have been proposed and patented.
  • a stacking method in which R (Red), G (Green) and B (Blue) light emitting parts are arranged side by side, and R, G and B light emitting layers are stacked up and down
  • 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 from the electroluminescence material.
  • CCM color conversion material
  • the organic electroluminescent device may be one of an organic electroluminescent device, an organic solar cell, an organophotoreceptor, an organic transistor, or a device for monochromatic or white illumination.
  • Another embodiment of the present invention can include an electronic device including a display device including the above-described organic electronic device of the present invention and 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.
  • a compound according to one aspect of the present invention is represented by the following formula (1).
  • each symbol may be defined as follows.
  • a rings are independently of each other C 6 -C 60 aromatic hydrocarbons; Fluorene; O, N, S, C 2 ⁇ C 60 heteroaryl rings containing Si and P, at least one of the hetero atoms in the; And a fused ring of a C 6 to C 60 aromatic ring and a C 3 to C 60 aliphatic ring.
  • a ring is deuterium; halogen; A silane group substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms; Siloxyl group; Boron group; Germanium group; Cyano; A nitro group; An alkyl thio group of C 1 -C 20 ; A C 1 -C 20 alkoxyl group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; A C 2 -C 20 alkynyl group; A C 6 -C 20 aryl group; A C 6 -C 20 aryl group substituted by deuterium; A fluorenyl group; A C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; A C 3 -C 20 cycloalkyl group; An arylalkyl group of C 7 -C 20 ; Aryl
  • the ring A is an aromatic hydrocarbon
  • it may preferably be a C 6 -C 30 aromatic hydrocarbon, more preferably a C 6 -C 14 aromatic hydrocarbon, specifically, benzene, naphthalene, phenanthrene, and the like.
  • X 1 and X 2 independently represent a single bond, N (L 1 ) (Ar 1 ), O, S, C (R ') (R ”) or Si (R') (R").
  • L 1 represents a single bond of C 6 to C 60 ; An arylene group; A fluorenylene group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; And a fused ring group of an aromatic ring of C 6 to C 60 and an aliphatic ring of C 3 to C 60 .
  • L 1 When L 1 is an arylene group, it may preferably be an arylene group having 6 to 30 carbon atoms, more preferably an arylene group having 6 to 12 carbon atoms, specifically, phenyl, naphthalene, biphenyl, and the like.
  • L 1 When L 1 is a heterocyclic group, preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 13 heterocyclic group, specifically, pyridine, pyrimidine, triazine, quinazoline, Quinoxaline, phthalazine, carbazole, pyridopyrimidine, benzoquinoline, phenanthridine benzothienopyrimidine, benzopuropyrimidine, and the like.
  • Ar 1 is a C 6 to C 60 aryl group; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aliphatic ring of C 3 to C 60 and an aromatic ring of C 6 to C 60 ; And -L 2 -N (R a ) (R b ).
  • Ar 1 is an aryl group, it may preferably be an aryl group of C 6 to C 30 , more preferably a C 6 to C 12 aryl group, specifically, phenyl, biphenyl, naphthyl, and the like.
  • Ar 1 is a heterocyclic group, preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 18 heterocyclic group, specifically, pyridine, pyrimidine, triazine, quinazoline, benzothiazole, Benzopyrimidine, benzoquinazoline, quinoxaline, phthalazine, carbazole, pyridopyrimidine, benzoquinoline, phenanthridine, indolocarbazole, dibenzofurane, and the like.
  • R 'and R " are independently selected from the group consisting of a C 1 to C 50 alkyl group, a C 6 to C 60 aryl group, a C 2 to C 60 alkyl group having at least one heteroatom selected from O, N, S, , And R 'and R " may be bonded to each other to form a ring.
  • R 1 to R 9 independently of one another are hydrogen; heavy hydrogen; halogen; A C 6 to C 60 aryl group; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aromatic ring of C 6 to C 60 and an aliphatic ring of C 3 to C 60 ; A C 1 to C 50 alkyl group; An alkenyl group having 2 to 20 carbon atoms; A C 1 to C 30 alkoxyl group; An aryloxy group of C 6 to C 30 ; And -L 2 -N (R a ) (R b ), and neighboring groups may be bonded to each other to form a ring.
  • L < 2 &gt is a single bond; A C 6 to C 60 aryl group; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; And a fused ring group of an aromatic ring of C 6 to C 60 and an aliphatic ring of C 3 to C 60 .
  • R a and R b are each independently a C 6 to C 60 aryl group; A fluorenyl group; A fused ring group of an aliphatic ring of C 3 to C 60 and an aromatic ring of C 6 to C 60 ; And a C 2 to C 60 heterocyclic group containing at least one hetero atom selected from the group consisting of O, N, S, Si and P, and R a and R b may be bonded to each other to form a ring have.
  • the formula (1) may be represented by one of the following formulas (2) to (41).
  • X 1 and X 2 are the same as defined in Formula (1), and in Formulas (10) to (17), R 1 to R 9 are as defined in Formula , Ar 1 is as defined in formula (1), and R 'and R "in the above formulas (18) to (25) are as defined in formula (1).
  • R 10 to R 17 independently represent hydrogen; heavy hydrogen; halogen; A C 6 to C 60 aryl group; A fluorenyl group; A C 2 to C 60 heterocyclic group containing at least one heteroatom selected from O, N, S, Si and P; A fused ring group of an aromatic ring of C 6 to C 60 and an aliphatic ring of C 3 to C 60 ; A C 1 to C 50 alkyl group; An alkenyl group having 2 to 20 carbon atoms; A C 1 to C 30 alkoxyl group; An aryloxy group of C 6 to C 30 ; And -L 2 -N (R a ) (R b ), wherein L 2 , R a and R b are as defined in formula (1).
  • Formula 1 may be one of the following compounds.
  • an organic electroluminescent device comprising a first electrode, a second electrode, and an organic material layer disposed between the first electrode and the second electrode.
  • the organic material layer is at least one of a hole injecting layer, a hole transporting layer, a light emitting auxiliary layer, and a light emitting layer, and the organic material layer may include at least one of the compounds.
  • the organic material layer may include one or more compounds represented by the formula (1), and the compound represented by the formula (1) may be used as a material for the emission coarsening layer or a host material for the emission layer, in particular, a red phosphorescent host material .
  • the compound of formula (1) according to the present invention can be prepared by a reaction route as shown in the following reaction formula (1), but is not limited thereto.
  • one of Z 1 and Z 2 is -NH and the other is a single bond.
  • N- bromosuccinimide (3.33 g, 18.71 mmol) and DMF (50 mL) were added to a solution of Core-1-c (4.3 g, 17.82 mmol) and the mixture was stirred at room temperature for 6 hours. When the reaction was completed, it was extracted with MC and wiped with water. The organic layer was dried over MgSO 4 and concentrated. The resulting organic material was separated using a silicagel column to obtain 4.39 g (77%) of the product.
  • Core-1-d (3.9 g, 12.18 mmol), 1-chloronaphthalen-2-amine (2.16 g, 12.18 mmol), Pd 2 (dba) 3 (0.33 g, 4.27 g (84%) of the product was obtained using the above Core-1-e synthesis method by adding 1.29 g, 13.40 mmol), P (t-bu) 3 (0.25 g, 1.22 mmol) and toluene (50 ml).
  • Core-2-a (3.10 g , 7.44 mmol), Pd (OAc) 2 (0.08 g, 0.37 mmol), P (t-Bu) 3 (0.22 g, 0.74 mmol), K 2 CO 3 (3.08 g, 22.31 mmol) and DMA (50 ml) were subjected to the synthesis of Core-1 to obtain 2.32 g (82%) of the product.
  • Triphenylphosphine (28.05 g, 106.93 mmol) and o-dichlorobenzene (o-DCB) (150 ml) were added to Core-5-a (15.50 g, 42.77 mmol) and refluxed at 180 ° C for 6 hours.
  • o-DCB o-dichlorobenzene
  • the temperature of the reaction is cooled to room temperature and o-DCB is removed.
  • the resulting organic material was separated by silicagel column to obtain 13.00 g (92%) of product.
  • the Core-1-d (5.30 g , 16.55 mmol) (3-nitronaphthalen-2-yl) boronic acid (3.59 g, 16.55 mmol), Pd (PPh 3) 4 (0.57 g, 0.50 mmol), K 2 CO 3 6.08 g (89%) of the product was obtained by using the above Core-5-a synthesis method with the above compound (3.43 g, 24.83 mmol), THF (100 ml) and H 2 O (50 ml)
  • Core-1-d (6.20 g , 19.36 mmol) (1-nitronaphthalen-2-yl) the boronic acid (4.20 g, 19.36 mmol ), Pd (PPh 3) 4 (0.67 g, 0.58 mmol), K 2 CO 3 7.03 g (88%) of the product was obtained by using the Core-5-a synthesis method described above (4.01 g, 29.05 mmol), THF (100 ml) and H 2 O (50 ml).
  • One of X 1 and X 2 is S, O or CR'R "and the other is a single bond.
  • N -iodosuccimide (9.11 g, 40.47 mmol) and DMF (150 mL) were added to a solution of Core-1-c (9.30 g, 38.54 mmol) and the mixture was stirred at room temperature for 6 hours. When the reaction was completed, it was extracted with MC and wiped with water. The organic layer was dried over MgSO 4 and concentrated. The resulting organic material was separated using a silicagel column to obtain 9.26 g (75%) of the product.
  • Core-10-a (6.80 g , 18.52 mmol) to methyl 5-bromo-2-iodobenzoate (6.31 g, 18.52 mmol), Pd (PPh 3) 4 (0.64 g, 0.56 mmol), K 2 CO 3 (3.84 g , 27.77 mmol), THF (100 ml) and H 2 O (50 ml) were used to synthesize Core-10-b to give 3.53 g (42%) of the product.
  • the compound belonging to Sub 1 may be, but not limited to, the following compounds, and Table 1 shows the FD-MS value of the compound belonging to Sub 1.
  • Core-9 (3.30 g, 6.97 mmol), Sub-1-62 (1.95 g, 6.97 mmol), Pd (PPh 3) 4 (0.24 g, 0.21 mmol), K 2 CO 3 (1.45 g, 10.46 mmol), THF (80 ml) and H 2 O (40 ml) were used to synthesize Core-5-a to obtain 3.62 g (88%) of the product.
  • Core-10 (6.50 g, 14.21 mmol), Sub 1-67 (8.55 g, 14.21 mmol), Pd (PPh 3) 4 (0.49 g, 0.43 mmol), K 2 CO 3 (2.95 g, 21.32 mmol), THF (80 ml) and H 2 O (40 ml) were subjected to the synthesis of Core-5-a to obtain 6.47 g (85%) of the product.
  • Core-11 (3.60 g, 7.45 mmol), Sub-1-14 (2.37 g, 7.45 mmol), Pd (PPh 3) 4 (0.26 g, 0.22 mmol), K 2 CO 3 (1.54 g, 11.17 mmol), THF (100 ml) and H 2 O (50 ml) were subjected to the synthesis of Core-5-a to obtain 3.90 g (82%) of the product.
  • a 4,4 ', 4 "-tris [2-naphthyl (phenyl) amino] triphenylamine (hereinafter abbreviated as" 2-TNATA ”) film was vacuum deposited on the ITO layer (anode) After the formation of the injection layer, a 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (hereinafter abbreviated as NPD) film was vacuum deposited to a thickness of 60 nm to form a hole transport layer.
  • NPD 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl
  • An organic electroluminescence device was prepared in the same manner as in Example 1, except that the compound of the present invention described in Table 3 was used instead of the compound P-1 of the present invention as a host material of the light emitting layer.
  • An organic electroluminescence device was prepared in the same manner as in Example 1 except that one of the following Comparative Compounds A to C was used in place of the compound P-1 of the present invention as a host material in the light emitting layer.
  • Electruminescence (EL) characteristics were measured with a photoresearch PR-650 by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 1 to 53 and Comparative Examples 1 to 3 of the present invention And the T95 lifetime was measured using a life measuring instrument manufactured by Mac Science Inc. at a luminance of 2500 cd / m 2. The measurement results are shown in Table 3 below.
  • the organic electroluminescent device using the compound of the present invention as a phosphorescent host material has a lower driving voltage and significantly improved luminous efficiency and lifetime than the case of using a comparative compound.
  • Comparative Compound A which is a CBP mainly used as a host material
  • Comparative Compound B and Comparative Compound C when the indolopyrrolocarbazole was the main skeleton of Comparative Compound B and Comparative Compound C were used as the host material, the device characteristics were improved, and Comparative Compound B and Comparative Compound C, the device characteristics were further improved when the compound of the present invention was used as a host material.
  • Compounds of the present invention are more fused with one or more benzene in the main skeleton than the comparative compounds B and C.
  • one or more benzene is fused in the main skeleton, and physical properties such as HOMO value, T 1 value, and thermal stability are changed.
  • the difference in physical properties is a main factor Energy balance), resulting in different device results.
  • 2-TNATA was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to a thickness of 60 nm to form a hole injection layer
  • NPB was vacuum-deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer.
  • the compound P-18 of the present invention was vacuum deposited on the hole transport layer to a thickness of 20 nm to form a light-emission-assisting layer, and then 4,4'-N, N'-dicarbazole- biphenyl (hereinafter abbreviated as " CBP ") was doped with 95: 5 by weight of dopant (piq) 2 Ir (acac) to form a 30 nm thick light emitting layer.
  • BAlq was vacuum-deposited on the light emitting layer to form a hole blocking layer to a thickness of 10 nm, and Alq 3 was formed to a thickness of 40 nm on the hole blocking layer to form an electron transporting layer.
  • LiF which is an alkali metal halide, was deposited on the electron transport layer to a thickness of 0.2 nm to form an electron injection layer, and Al was deposited to a thickness of 150 nm on the electron injection layer to form a cathode.
  • An organic electroluminescent device was prepared in the same manner as in Example 54 except that the compound of the present invention described in Table 4 was used instead of the compound P-18 of the present invention as a material of the luminescent auxiliary layer.
  • An organic electroluminescent device was prepared in the same manner as in Example 54 except that no luminescent auxiliary layer was formed.
  • An organic electroluminescence device was prepared in the same manner as in Example 54, except that the following compound D or Comparative Compound F was used in place of the compound P-18 of the present invention as a material of the luminescent auxiliary layer.
  • Electruminescence (EL) characteristics were measured with a photoresearch PR-650 by applying a forward bias DC voltage to the organic electroluminescent devices manufactured in Examples 54 to 62 and Comparative Examples 4 to 6 of the present invention And the T95 lifetime was measured using a life measuring apparatus manufactured by Mac Science Inc. at a luminance of 2500 cd / m 2. The measurement results are shown in Table 4 below.
  • the red organic light emitting device using the compound of the present invention as the light emitting auxiliary layer material has a lower driving voltage than the comparative example in which no luminescent auxiliary layer is formed or Comparative Compound D and Comparative Compound F are used The efficiency, and the life span were remarkably improved.
  • Comparative Example 5 and Comparative Example 5 using the comparative compound D or the comparative compound F were superior to those of the comparative example 4 in which the luminescent auxiliary layer was not used.
  • the compound of the present invention was used in comparison with the comparative compound D or the comparative compound F The device characteristics were the best.

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Abstract

La présente invention concerne : un composé représenté par la formule chimique 1 ; un dispositif électronique organique comprenant une première électrode, une seconde électrode et une couche organique entre la première électrode et la seconde électrode ; et un appareil électronique le comprenant, le composé représenté par la formule chimique 1 étant contenu dans la couche organique, ce qui permet de diminuer la tension de commande du dispositif électronique organique et d'améliorer l'efficacité lumineuse et la durée de vie.
PCT/KR2018/008146 2017-07-25 2018-07-19 Composé pour dispositif électronique organique, dispositif électronique organique l'utilisant et appareil électronique associé Ceased WO2019022435A1 (fr)

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US12150378B2 (en) 2019-10-07 2024-11-19 Samsung Display Co., Ltd. Luminescence device and polycyclic compound for luminescence device
US12227523B2 (en) 2021-01-14 2025-02-18 Samsung Display Co., Ltd. Luminescence device and polycyclic compound for luminescence device
US12528820B2 (en) 2019-10-07 2026-01-20 Samsung Display Co., Ltd. Luminescence device and polycyclic compound for luminescence device

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KR102628728B1 (ko) * 2020-08-31 2024-01-23 주식회사 엘지화학 다환 화합물 및 이를 포함하는 유기 발광 소자

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US12150378B2 (en) 2019-10-07 2024-11-19 Samsung Display Co., Ltd. Luminescence device and polycyclic compound for luminescence device
US12528820B2 (en) 2019-10-07 2026-01-20 Samsung Display Co., Ltd. Luminescence device and polycyclic compound for luminescence device
CN111704621A (zh) * 2020-06-24 2020-09-25 上海天马有机发光显示技术有限公司 化合物、显示面板及显示装置
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