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WO2019027163A1 - Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique l'utilisant - Google Patents

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

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WO2019027163A1
WO2019027163A1 PCT/KR2018/008205 KR2018008205W WO2019027163A1 WO 2019027163 A1 WO2019027163 A1 WO 2019027163A1 KR 2018008205 W KR2018008205 W KR 2018008205W WO 2019027163 A1 WO2019027163 A1 WO 2019027163A1
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소기호
이윤석
박정환
김경철
조민지
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DukSan Neolux Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D487/02—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
    • C07D487/04—Ortho-condensed systems
    • 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
    • C07D491/02—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
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
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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
    • 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
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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
    • H10K85/615—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
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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

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 multilayer structure composed of different materials, and may be formed of 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 decreases. As the driving voltage decreases, the crystallization of the organic material due to Joule heating, which occurs during driving, Indicating a tendency for the lifetime to increase. However, simply improving the organic material layer can not maximize the efficiency. This is because, when the optimum combination of the energy level and the T 1 value between the respective 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.
  • a luminescent auxiliary layer exists between the hole transporting layer and the luminescent layer, and the luminescent layer (R, G, B) It is necessary to develop another light-emitting auxiliary layer.
  • electrons are transferred from the electron transport layer to the light emitting layer, and holes are transferred from the hole transport layer to the light emitting layer to generate excitons by recombination.
  • the material used for the hole transport layer has a low HOMO value, it has a low T 1 value, which causes the exciton generated in the light emitting layer to be transferred to the hole transport layer.
  • charge imbalance in the light emitting layer unbalance, and emits light at the hole transporting layer or at the interface of the hole transporting layer, resulting in deterioration of color purity, reduction in efficiency, and reduction in lifetime.
  • the efficiency tends to decrease. This is because the hole mobility is faster than the electron mobility in a general organic electroluminescent device, resulting in a charge unbalance in the light emitting layer, resulting in a decrease in efficiency and a reduction in lifetime.
  • the light-emission-assisting layer has a hole mobility (within a full device blue device driving voltage range) to have a proper driving voltage capable of solving the problems of the hole transport layer and a high T 1 (electron block ) Value, and a wide band gap.
  • this can not be achieved simply by the structural properties of the core of the light-emitting auxiliary layer material, but when the combination of the core and sub-substituent characteristics of the material is possible. Therefore, in order to improve the efficiency and lifetime of an organic electronic device, development of a light emitting auxiliary layer material having a high T 1 value and a wide band gap is urgently required.
  • 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.
  • materials constituting the organic material layer in the device such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material, an electron injecting material, which is supported by an efficient material.
  • a hole injecting material a hole transporting material
  • a light emitting material a hole transporting material
  • an electron transporting material an electron injecting material
  • 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 preferably the material for the hole transporting layer 140 and / .
  • 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 hole transport layer 140 and / or the light-emitting auxiliary layer 151 are formed using the compound represented by the general formula (1), whereby the energy level and the T 1 value between the organic layers, Characteristics, etc.) can be optimized to improve the lifetime and efficiency of the organic electronic device 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 electroluminescent 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.
  • X 1 and X 2 are independently of each other NL a -Ar a , O or S;
  • L a independently represents a single bond; An arylene group having 6 to 60 carbon atoms; 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 a is an arylene group, it is preferably 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.
  • Ar a 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; And fused ring groups of the aromatic ring of C 3 ⁇ C 60 of aliphatic rings and C 6 ⁇ C 60; is selected from the group consisting of.
  • Ar a 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, naphthalene, biphenyl, and the like.
  • R 1 and R 2 are independently of each other 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; And an aryloxy group having 6 to 30 carbon atoms, and adjacent R 1 groups or adjacent R 2 groups may be bonded to each other to form a ring.
  • a and b are each an integer of 0 to 3, and when each of these is an integer of 2 or more, a plurality of R 1 s may be the same or different, and a plurality of R 2 s may be the same or different from each other.
  • a ring formed by bonding adjacent R 1 s or adjacent R 2 s to each other is a C 2 to C 60 aromatic hydrocarbon, fluorene, C 2 containing at least one hetero atom selected from O, N, S, Si and P - be a heterocyclic group of C 60, or C-3 of the aromatic ring of the fused ring of C 60 alicyclic and C 6 - C 60, and can specifically or the like benzene, naphthalene, phenanthrene.
  • L 1 and L 2 independently of one another are a single bond; An arylene group having 6 to 60 carbon atoms; 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 and L 2 are arylene groups, it is preferably an arylene group of C 6 to C 30 , more preferably an arylene group of C 6 to C 12 , specifically, phenyl, naphthalene, biphenyl and the like.
  • L 1 and L 2 are a heterocyclic group, it is preferably a C 2 to C 30 hetero ring, more preferably a C 2 to C 12 hetero ring, specifically a dibenzothiophene, a dibenzofurane, or the like.
  • Y is O or S
  • L 3 is a single bond; An arylene group having 6 to 60 carbon atoms; 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 .
  • R 3 and R 4 are independently of each other 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; And an aryloxy group of C 6 to C 30 ; adjacent groups may be bonded to each other to form a ring, c is an integer of 0 to 3, and d is an integer of 0 to 4. When c is an integer of 2 or more, the plurality of R 3 may be the same or different, and when d is an integer of 2 or more, the plurality of R 4 may be the same or different from each other.
  • Ar 1 to Ar 4 Is preferably an aryl group of C 6 to C 30 , more preferably a C 6 to C 18 aryl group, specifically, phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, Chrysene, and the like.
  • Ar 1 to Ar 4 Is a heterocyclic group, preferably a C 2 to C 30 hetero ring, more preferably a C 2 to C 18 hetero ring, specifically, pyridine, isoquinoline, dibenzothiophene, dibenzofuran, benzonaphtho Thiophene, benzonaphthofuran, carbazole, phenylcarbazole, benzothienopyrimidine, and the like.
  • Ar 1 to Ar 4 Is 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene and the like.
  • each symbol represents an aryl group, an arylene group, a fluorenyl group, a fluorenylene group, a heterocyclic group, a fused ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, Or adjacent R 1 , adjacent R 2 , adjacent R 3 or adjacent R 4 bond to each other to form a ring, each of which may be substituted by 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
  • the formula (1) may be represented by one of the following formulas (1) to (16).
  • R 1 , R 2 , a, b, X 1 , X 2 , L 1 , L 2 , Ar 2 to Ar 4 and Y are as defined in Chemical 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. That is, the organic material layer may include one or more compounds represented by Formula 1, and the compound represented by Formula 1 may be used as a material for the hole transport layer or the light-emitting auxiliary layer.
  • an electronic device including a display device including the organic electroluminescent device and a control unit for driving the display device, ≪ / RTI >
  • the compound of formula (I) according to the present invention (Final Products) can be prepared by the reaction path of Scheme 1 below.
  • Sub 1 of Reaction Scheme 1 can be synthesized by the reaction path of Reaction Scheme 2, but is not limited thereto.
  • N-chlorosuccinimide (23.86 g, 178.70 mmol) was dissolved in Methylenchlororide and refluxed for 6 hours. The reaction mixture was stirred at room temperature for 3 hours, . At the end of the reaction, the reaction product was extracted with Ethylacetate and wiped with water. After removal of a small amount of water over anhydrous MgSO 4 and filtered under reduced pressure, re-crystallization and the desired 8-bromo-2-chloro- 6H-benzo The resulting product was concentrated in an organic solvent [4,5] thieno [2,3-b ] 54.1 g of indole was obtained. (Yield: 90%).
  • N-chlorosuccinimide (26.16 g, 195.89 mmol) was dissolved in methylenechloride and refluxed for 6 hours. At the end of the reaction, the reaction product was extracted with Ethylacetate and wiped with water. It removed a small amount of water over anhydrous MgSO 4 and then filtered under reduced pressure, and recrystallized to give the resultant product by concentration of the organic solvent 59.5 g of the desired 8-bromo-2-chloro- 6H-benzofuro [2,3-b] indole. (Yield: 90%).
  • N-phenyldibenzo [b, d] thiophen-3-amine (35.0 mmol) was added to a solution of 8-bromo-2-chloro-5,6-diphenyl-5,6-dihydroindolo [ g, 127.18 mmol), Pd 2 (dba) 3 (0.03 eq.), (t-Bu) 3 P (0.06 eq.) and NaOt-Bu (3 eq.) were dissolved in anhydrous toluene and refluxed for 3 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with CH 2 Cl 2 and wiped with water.
  • Phenyldibenzo [b, d] thiophen-4-amine 38.9 g, 141.37 mmol was added to a solution of 8-bromo-2-chlorobenzo [b] benzo [4,5] thieno [ 141.37 mmol), Pd 2 (dba) 3 (0.03 eq.), (T-Bu) 3 P (0.06 eq.) And NaOt-Bu (3 eq.)
  • the temperature of the reaction mixture was cooled to room temperature, extracted with CH 2 Cl 2 and wiped with water.
  • 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.
  • Sub 2 of Reaction Scheme 1 may be synthesized by the reaction path of the following Reaction Scheme 7, but is not limited thereto.
  • the compounds belonging to Sub 2 may be, but not limited to, the following compounds, and Table 2 shows FD-MS values of the compounds belonging to Sub 2.
  • 6-dibenzo [b, d] furan-2-yl) -N, 6-diphenyl-6H-benzofuro [2,3- b] indol-8-amine (10 g, 17.39 mmol) after dissolved (2.94 g, 17.39 mmol), Pd 2 (dba) 3 (0.03 eq.), (t-Bu) 3P (0.06 equivalent), NaOt-Bu (3 eq.) in anhydrous Toluene, was refluxed for 3 hours .
  • the temperature of the reaction mixture was cooled to room temperature, extracted with CH 2 Cl 2 and wiped with water.
  • Benzo [4,5] thieno [2,3-b] benzofuran-8-amine (10 g, 10 mmol) was added to a solution of 2-chloro-N- (dibenzo [b, d] furan- after dissolving the 18.87 mmol), diphenylamine (3.19 g , 18.87 mmol), Pd 2 (dba) 3 (0.03 eq.), (t-Bu) 3P (0.06 equivalent), NaOt-Bu (3 eq.) in anhydrous Toluene, And refluxed for 3 hours. When the reaction was completed, the temperature of the reaction mixture was cooled to room temperature, extracted with CH 2 Cl 2 and wiped with water.
  • N 1 on the ITO layer (anode) formed on the glass substrate - (naphthalen-2-yl) -N 4, N 4 -bis (4- (naphthalen-2-yl (phenyl) amino) phenyl) -N 1 -phenylbenzene -1,4-diamine (abbreviated as " 2-TNATA " hereinafter) was vacuum-deposited to a thickness of 60 nm to form a hole injection layer.
  • 4,4-bis [N- (Hereinafter abbreviated as " NPD ") was vacuum-deposited to a thickness of 60 nm to form a hole transport layer.
  • Compound P-1 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 4,4'-N, N'-dicarbazole-biphenyl (Hereinafter abbreviated as "(piq) 2 Ir (acac)”) bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate (hereinafter abbreviated as "CBP” 5 weight ratio to form a light emitting layer having a thickness of 30 nm.
  • (piq) 2 Ir (acac) bis- (1-phenylisoquinolyl) iridium (III) acetylacetonate
  • BAlq was vacuum-deposited on the light-emitting layer to a thickness of 5 nm to form a hole blocking layer
  • Bis (10-hydroxybenzo [h] quinolinato) beryllium (hereinafter referred to as "BeBq 2 " ) was vacuum-deposited to a thickness of 40 nm to form an electron transport layer.
  • LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer
  • 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 1 except that the compound of the present invention described in Table 4 was used instead of the compound P-1 of the present invention as the luminescent auxiliary layer material.
  • An organic electroluminescence device was fabricated in the same manner as in Example 1 except that no luminescent auxiliary layer was formed.
  • An organic electroluminescent device was prepared in the same manner as in Example 1 except that the following compounds 1 to 3 were used instead of the compound P-1 of the present invention as the luminescent auxiliary layer material.
  • a forward bias DC voltage was applied to the thus fabricated organic EL devices of Examples 1 to 30 and Comparative Examples 1 to 4 to measure electroluminescence (EL) characteristics with PR-650 of a photoresearch company And the T95 lifetime was measured by a life measuring device manufactured by Mac Science Inc. at a reference luminance of 2500 cd / m 2 .
  • Table 4 shows the results of device fabrication and evaluation.
  • the device results of the comparative examples 2 to 4 using the comparative compounds 1 to 3 were superior to those of the comparative example 1 where no luminescent auxiliary layer was formed.
  • a specific substituent group such as dibenzothiophene (hereinafter, referred to as 'DBT') or dibenzofuran (hereinafter referred to as 'DBF') is introduced into the amino group.
  • 'DBT' dibenzothiophene
  • 'DBF' dibenzofuran
  • the HOMO or LUMO energy level of the compound of the present invention has an appropriate value between the hole transporting layer and the light emitting layer, balance, and light emission is performed inside the light emitting layer rather than at the interface of the hole transporting layer, thereby maximizing the efficiency and lifetime.
  • Example 1 when the results of Example 1, Example 7, Example 11, and Example 16 of the present invention are compared, when the heteroatom introduced into the quadrivalent heterocyclic core contains S or O, the efficiency and lifetime of the device are increased .
  • the compound has a higher refractive index when heteroatoms S and O are introduced than when a hetero atom N is introduced into the same core, resulting in an improvement in the efficiency and lifetime of the device.
  • Example 16 and Example 21 of the present invention are compared, it can be confirmed that the result of the device of Example 16 in which the amino group is bonded to the 2,3 or 4 position of the core is better than that of Example 21. Even though the same core is used, the substitution position of the amino group changes and the energy level is changed, and the physical properties of the compound are changed. Therefore, it is considered that these different results are obtained as a main factor for improving the device performance in the device deposition.
  • 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. Then, the compound P-1 of the present invention was vacuum deposited Thereby forming a hole transporting layer. Subsequently, CBP was doped with tris (2-phenylpyridine) -iridium (hereinafter referred to as "Ir (ppy) 3 ”) as a dopant on the hole transport layer at a weight ratio of 90:10, Thick luminescent layer was formed.
  • Ir (ppy) 3 tris (2-phenylpyridine) -iridium
  • BAlq was vacuum deposited on the light emitting layer to form a hole blocking layer to form a hole blocking layer
  • BeBq 2 was vacuum deposited to a thickness of 40 nm on the hole blocking layer to form an electron transporting layer.
  • LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer
  • Al was deposited to a thickness of 150 nm on the electron injection layer to form a cathode.
  • An organic light emitting device was fabricated in the same manner as in Example 31 except that the compound of the present invention described in Table 5 was used instead of the compound P-1 of the present invention as a hole transporting layer material.
  • a forward bias DC voltage was applied to the thus fabricated organic EL devices of Examples 31 to 40 and Comparative Examples 5 to 8, and electroluminescence (EL) characteristics were measured with photoresearch PR-650 And the T95 lifetime was measured by a lifetime measuring device manufactured by Mac Science Inc. at a reference luminance of 5000 cd / m 2 .
  • Table 5 shows the results of device fabrication and evaluation.
  • the chemical and physical characteristics of the compound of the present invention in which the dibenzothiophene or dibenzofuran substituent is necessarily introduced into two amine groups can be significantly different from those of the comparative compounds, Suggesting that it can be derived.
  • the correlation with the light emitting layer must be grasped. Even if similar cores are used, it would be very difficult for the ordinary skilled artisan to deduce the characteristics shown in the hole transporting layer in which the compound of the present invention is used.
  • the device characteristics of applying the compound of the present invention to only one of the hole transporting layer and the light-emitting auxiliary layer have been described.
  • the present invention is also applicable to the case where both the hole transporting layer and the light- It will be possible.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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Abstract

L'invention concerne : un composé représenté par la formule chimique 1 ; un élément électrique organique comprenant une première électrode, une seconde électrode et une couche de matériau organique entre la première électrode et la seconde électrode ; et un dispositif électronique le comprenant, l'inclusion du composé représenté par la formule chimique 1 dans la couche de matériau organique pouvant diminuer la tension de commande de l'élément électrique organique et améliorer le rendement lumineux et la durée de vie de l'élément électrique organique.
PCT/KR2018/008205 2017-08-01 2018-07-20 Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique l'utilisant Ceased WO2019027163A1 (fr)

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EP3608320A1 (fr) * 2018-08-10 2020-02-12 Samsung Display Co., Ltd. Dispositif électroluminescent organique et composé cyclique condensé pour dispositif électroluminescent organique
CN111269234A (zh) * 2020-02-29 2020-06-12 华南理工大学 一种一步合成2-氨基吲哚并[2,3-b]吲哚衍生物的方法
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US12209095B2 (en) 2019-11-22 2025-01-28 Lg Chem, Ltd. Compound and organic light-emitting device comprising same
KR102843722B1 (ko) * 2020-02-12 2025-08-07 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
KR20250069745A (ko) * 2023-11-10 2025-05-20 덕산네오룩스 주식회사 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자장치

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