WO2021029598A1 - Composé pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique associé - Google Patents

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

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WO2021029598A1
WO2021029598A1 PCT/KR2020/010341 KR2020010341W WO2021029598A1 WO 2021029598 A1 WO2021029598 A1 WO 2021029598A1 KR 2020010341 W KR2020010341 W KR 2020010341W WO 2021029598 A1 WO2021029598 A1 WO 2021029598A1
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organic
heteroatom
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강문성
김지영
이윤석
이남걸
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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • 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
    • 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
    • H10K85/6574—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 thereof.
  • the organic light emission phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
  • An organic electric device using an organic light emission phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electronic device, and may be formed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • Materials used as an organic material layer in an organic electric device can be classified into light-emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron transport materials, and electron injection materials, according to their functions.
  • the light-emitting material may be classified into a high molecular type and a low molecular type according to its molecular weight, and according to a light emitting mechanism, it may be classified into a fluorescent material derived from the singlet excited state of the electron and a phosphorescent material derived from the triplet excited state of the electron have.
  • the light-emitting material may be classified into blue, green, and red light-emitting materials and yellow and orange light-emitting materials necessary for realizing a better natural color according to the light-emitting color.
  • a host/dopant system may be used as a light emitting material in order to increase the luminous efficiency through.
  • the principle is that when a small amount of a dopant having an energy band gap smaller than that of the host forming the light emitting layer is mixed in the light emitting layer, excitons generated in the light emitting layer are transported to the dopant to emit light with high efficiency. At this time, since the wavelength of the host moves to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant used.
  • 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, the crystallization of organic substances caused by Joule heating during driving decreases. It shows a tendency to increase the lifespan. However, simply improving the organic material layer cannot maximize the efficiency. This is because long life and high efficiency can be achieved at the same time when the energy level and T 1 value between each organic material layer, and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined. .
  • An object of the present invention is to provide a compound capable of lowering a driving voltage of a device and improving luminous efficiency and lifetime of a device, an organic electric device using the same, and an electronic device thereof.
  • the present invention provides a compound represented by the following formula.
  • the present invention provides an organic electric device and an electronic device using the compound represented by the above formula.
  • the compound according to an embodiment of the present invention not only can the driving voltage of the device be lowered, but also the luminous efficiency, color purity, stability, and lifespan of the device can be greatly improved.
  • 1 to 3 are exemplary views of an organic electroluminescent device according to the present invention.
  • organic electric device 110 first electrode
  • first hole transport layer 340 first emission layer
  • second charge generation layer 420 second hole injection layer
  • aryl group and arylene group used in the present invention each have 6 to 60 carbon atoms, and are not limited thereto.
  • the aryl group or the arylene group may include a monocyclic type, a ring aggregate, a conjugated ring system, a spiro compound, and the like.
  • a fluorenyl group may be included in the aryl group, and a fluorenylene group may be included in the arylene group.
  • fluorenyl group used in the present invention refers to a substituted or unsubstituted fluorenyl group
  • fluorenylene group refers to a substituted or unsubstituted fluorenyl group, and the fluorenyl group or
  • the fluorenylene group includes a spiro compound formed by bonding of R and R′ to each other in the following structure, and also includes a compound in which neighboring R′′ is bonded to each other to form a ring.
  • Substituted fluorenyl group and “substituted fluorenylene group” means that at least one of R, R', R" in the following structure is a substituent other than hydrogen, and in the formula below, R" is 1 to 8 days I can.
  • a fluorenyl group, a fluorenylene group, and a fluorenetriyl group may all be referred to as fluorene groups regardless of the valence.
  • spyro compound as used in the present invention has a'spyro linkage', and the spyro linkage refers to a linkage made by two rings sharing only one atom. At this time, the atoms shared in the two rings are referred to as'spiro atoms', and these are respectively referred to as'monospiro-','dispiro-', and'trispyro-' depending on the number of spiro atoms in a compound. 'It is called a compound.
  • heterocyclic group includes not only an aromatic ring such as a “heteroaryl group” or a “heteroarylene group”, but also a non-aromatic ring, and unless otherwise stated, each carbon number including one or more heteroatoms It means a ring of 2 to 60, but is not limited thereto.
  • heteroatom refers to N, O, S, P, or Si unless otherwise specified, and the heterocyclic group is a monocyclic type containing a heteroatom, a ring aggregate, a conjugated ring system, spy It means a compound and the like.
  • aliphatic ring group used in the present invention refers to cyclic hydrocarbons excluding aromatic hydrocarbons, and includes monocyclic, cyclic aggregates, conjugated cyclic systems, spiro compounds, etc., unless otherwise stated, It refers to a ring of 3 to 60, but is not limited thereto.
  • benzene as an aromatic ring and cyclohexane, a non-aromatic ring, are fused to an aliphatic ring.
  • the'group name' corresponding to the aryl group, arylene group, heterocyclic group, etc. exemplified as examples of each symbol and its substituent may describe'the name of the group reflecting the number', but it is described as the'parent compound name' You may.
  • the monovalent'group' is'phenanthryl' and the divalent group can be labeled with the valence by dividing the valency such as'phenanthrylene'. Regardless, it may be described as the parent compound name'phenanthrene'.
  • pyrimidine even in the case of pyrimidine, it may be described as'pyrimidine' regardless of the valence, or in the case of monovalent, it may be described as the'name of the group' of the corresponding valency, such as a pyrimidinyl group and in the case of divalent, have.
  • the substituent R 1 means that the substituent R 1 does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbon forming the benzene ring. It may be omitted and the formula or compound may be described.
  • a is an integer of 1
  • one substituent R 1 is bonded to any one of carbons forming a benzene ring, and when a is an integer of 2 or 3, it may be bonded, for example, as follows, and a is 4 to 6
  • R 1 may be the same or different from each other.
  • a number in'number-condensed ring' indicates the number of condensed rings.
  • a form in which three rings are condensed with each other, such as anthracene, phenanthrene, benzoquinazoline, etc. may be expressed as a 3-condensed ring.
  • a ring when expressed in the form of a'numeric resource' such as a five-membered ring or a six-membered ring, the number in'number-atomic' indicates the number of elements forming the ring.
  • thiophene or furan may correspond to a five-membered ring
  • benzene or pyridine may correspond to a six-membered ring.
  • the ring formed by bonding of adjacent groups to each other is a C 6 ⁇ C 60 aromatic ring group; Fluorenyl group; O, N, S, Si, and C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of P; And C 3 ⁇ C 60 aliphatic ring group; may be selected from the group consisting of.
  • the term'neighboring groups' refers to the following formula as an example, between R 1 and R 2, between R 2 and R 3, between R 3 and R 4 , Not only R 5 and R 6 but also R 7 and R 8 sharing one carbon are included, and are not immediately adjacent, such as between R 1 and R 7 , R 1 and R 8 or R 4 and R 5
  • Substituents bonded to ring elements may also be included.
  • substituents on a ring element such as carbon or nitrogen immediately adjacent to each other, they can be neighboring groups, but if no substituent is bonded to the ring element at the immediately adjacent position, it is bonded to the next ring element. It may be a group adjacent to the substituted substituent, and also the substituents bonded to the carbon constituting the same ring may be referred to as adjacent groups.
  • the expression'neighboring groups can be bonded to each other to form a ring' is used in the same meaning as'neighboring groups are selectively bonded to each other to form a ring', and at least one pair of It refers to a case where neighboring groups are bonded to each other to form a ring.
  • first, second, A, B, (a), and (b) may be used. These terms are only used to distinguish the component from other components, and the nature, order, or order of the component is not limited by the term.
  • a component is described as being “connected”, “coupled” or “connected” to another component, that component may be directly connected or connected to that other component, but another component between each component It should be understood that elements may be “connected”, “coupled” or “connected”.
  • a component such as a layer, film, region, or plate
  • it is not only “directly over” another component, as well as another component in the middle. It should be understood that cases may also be included. Conversely, it should be understood that when an element is “directly above” another part, it means that there is no other part in the middle.
  • 1 to 3 are exemplary views of an organic electric device according to an embodiment of the present invention.
  • an organic electric device 100 includes a first electrode 110, a second electrode 170, and a first electrode 110 formed on a substrate (not shown). ) And an organic material layer formed between the second electrode 170.
  • the first electrode 110 may be an anode (anode)
  • the second electrode 170 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 injection layer 120, a hole transport layer 130, a light emitting layer 140, an electron transport layer 150, and an electron injection layer 160.
  • the hole injection layer 120, the hole transport layer 130, the light emitting layer 140, the electron transport layer 150, and the electron injection layer 160 may be sequentially formed on the first electrode 110.
  • a light efficiency improvement layer 180 may be formed on one side of both surfaces of the first electrode 110 or the second electrode 170 not in contact with the organic material layer, and when the light efficiency improvement layer 180 is formed The light efficiency of the organic electric device can be improved.
  • the light efficiency improvement layer 180 may be formed on the second electrode 170.
  • the light efficiency improvement layer 180 is formed to form the second electrode 170.
  • optical energy loss due to SPPs surface plasmon polaritons
  • the light efficiency improvement layer 180 performs a buffering role for the second electrode 170 can do.
  • a buffer layer or a light emission auxiliary layer may be further formed between the hole transport layer 130 and the light emitting layer 140, which will be described with reference to FIG. 2.
  • an organic electric device 200 includes a hole injection layer 120, a hole transport layer 130, a buffer layer 210 sequentially formed on the first electrode 110, A light-emitting auxiliary layer 220, a light-emitting layer 140, an electron transport layer 150, an electron injection layer 160, and a second electrode 170 may be included, and a light efficiency improvement layer 180 is formed on the second electrode.
  • a hole injection layer 120 a hole transport layer 130, a buffer layer 210 sequentially formed on the first electrode 110
  • a light-emitting auxiliary layer 220, a light-emitting layer 140, an electron transport layer 150, an electron injection layer 160, and a second electrode 170 may be included, and a light efficiency improvement layer 180 is formed on the second electrode.
  • a light efficiency improvement layer 180 is formed on the second electrode.
  • an electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150.
  • the organic material layer may have a form in which a plurality of stacks including a hole transport layer, an emission layer, and an electron transport layer are formed. This will be described with reference to FIG. 3.
  • two stacks ST1 and ST2 formed of a multi-layered organic material layer are formed between the first electrode 110 and the second electrode 170.
  • a set or more may be formed, and a charge generation layer CGL may be formed between the stacks of organic material layers.
  • the organic electric device includes a first electrode 110, a first stack ST1, a charge generation layer (CGL), a second stack ST2, and a second electrode. 170 and a light efficiency improvement layer 180 may be included.
  • the first stack ST1 is an organic material layer formed on the first electrode 110, which is a first hole injection layer 320, a first hole transport layer 330, a first emission layer 340, and a first electron transport layer 350.
  • the second stack ST2 may include a second hole injection layer 420, a second hole transport layer 430, a second emission layer 440, and a second electron transport layer 450.
  • the first stack and the second stack may be organic material layers having the same laminated structure, but may be organic material layers having different laminated structures.
  • a charge generation layer CGL may be formed between the first stack ST1 and the second stack ST2.
  • the charge generation layer CGL may include a first charge generation layer 360 and a second charge generation layer 361.
  • the charge generation layer CGL is formed between the first emission layer 340 and the second emission layer 440 to increase current efficiency generated in each emission layer and smoothly distribute electric charges.
  • the first emission layer 340 may include a light-emitting material including a blue fluorescent dopant in a blue host, and the second emission layer 440 includes a material doped with a greenish yellow dopant and a red dopant in a green host. It may be included, but the material of the first emission layer 340 and the second emission layer 440 according to an embodiment of the present invention is not limited thereto.
  • n may be an integer of 1-5.
  • a charge generation layer CGL and a third stack may be additionally stacked on the second stack ST2.
  • the compound represented by Formula 1 of the present invention is a hole injection layer (120, 320, 420), a hole transport layer (130, 330, 430), a buffer layer (210), a light emission auxiliary layer (220), an electron transport layer (150, 350). , 450), the electron injection layer 160, the light emitting layer 140, 340, 440, or may be used as a material for the light efficiency improvement layer 180, but preferably the light emitting layer 140, 340, 440 and/or the light efficiency improvement layer It can be used as a material of 180.
  • band gap, electrical properties, and interfacial properties may vary depending on which substituent is bonded to any position of the same and similar core, a study on the selection of the core and the combination of sub-substituents bonded thereto In particular, long life and high efficiency can be achieved at the same time when the energy level and T 1 value between each organic material layer and the intrinsic properties of materials (mobility, interfacial properties, etc.) are optimally combined.
  • the compound represented by Formula 1 as a material for the light emitting layers 140, 340, and 440 and/or the light efficiency improvement layer 180, the energy level and T 1 value between each organic material layer, and the intrinsic properties of the material ( Mobility, interface characteristics, etc.) can be optimized to simultaneously improve the life and efficiency of the organic electric device.
  • the organic electroluminescent device may be manufactured using various deposition methods. It can be manufactured using a deposition method such as PVD or CVD. For example, a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate to form the anode 110, and a hole injection layer 120 thereon , After forming an organic material layer including the hole transport layer 130, the light emitting layer 140, the electron transport layer 150 and the electron injection layer 160, it can be produced by depositing a material that can be used as the cathode 170 thereon. have.
  • a deposition method such as PVD or CVD.
  • a metal or a conductive metal oxide or an alloy thereof is deposited on a substrate to form the anode 110, and a hole injection layer 120 thereon .
  • After forming an organic material layer including the hole transport layer 130, the light emitting layer 140, the electron transport layer 150 and the electron injection layer 160 it can be produced by depositing a material that can be used as the cathode 170 thereon. have
  • a light emitting auxiliary layer 220 between the hole transport layer 130 and the light emitting layer 140, and an electron transport auxiliary layer (not shown) between the light emitting layer 140 and the electron transport layer 150 may be further formed. It can also be formed in a stack structure as shown.
  • the organic material layer is a solution process or a solvent process other than a vapor deposition method using various polymer materials, such as spin coating process, nozzle printing process, inkjet printing process, slot coating process, dip coating process, roll-to-roll process, doctor blaze. It can be manufactured with fewer layers by a method such as a printing process, a screen printing process, or a thermal transfer method. 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 electric device according to an embodiment of the present invention may be of a top emission type, a bottom emission type, or a double side emission type depending on the material used.
  • the organic electric device may be selected from the group consisting of an organic electroluminescent device, an organic solar cell, an organic photoreceptor, an organic transistor, a monochromatic lighting device, and a quantum dot display device.
  • Another embodiment of the present invention may include a display device including the organic electric device 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 mobile communication terminals such as mobile phones, PDAs, electronic dictionaries, PMPs, remote controls, navigation, game consoles, various TVs, and various computers.
  • a compound according to an aspect of the present invention is represented by the following formula (1).
  • Y is O or S.
  • L 1 to L 3 are each independently a single bond; C 6 ⁇ C 60 arylene group; Fluorenylene group; C 3 ⁇ C 60 aliphatic ring group; And O, N, S, Si and P may be selected from the group consisting of a C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom.
  • the arylene group is preferably a C 6 to C 30 arylene group, more preferably a C 6 to C 18 arylene group such as phenylene or biphenyl It may be ene, naphthylene, terphenyl, and the like.
  • the heterocycle is preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 12 heterocyclic group, such as quinazoline, quinoc Saline, dibenzofuran, dibenzothiophene, and the like.
  • Ar 1 and Ar 2 are each independently a C 6 ⁇ C 60 aryl group; Fluorenyl group; And O, N, S, Si and P selected from the group consisting of a heterocyclic group of C 2 ⁇ C 60 containing at least one heteroatom, Ar 1 and Ar 2 at least one of the 2-condensation containing N It is a heterocyclic group of a ring.
  • the aryl group is preferably a C 6 to C 30 aryl group, more preferably a C 6 to C 18 aryl group such as phenyl, naphthyl, biphenyl, It may be terphenyl, triphenylene, phenanthrene, anthracene, pyrene, and the like.
  • the heterocycle is preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 25 heterocyclic group such as pyridine, quinoxaline , Quinoline, isoquinoline, pyridopyrimidine, quinazoline, naphthyridine, pyridopyrazine, phthalazine, dibenzothiophene, dibenzofuran, benzoimidazole, benzoxazole, spiro[fluorene-9, 9'-xanthene] and the like.
  • the fluorenyl group is 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spy It may be robin fluorene and the like.
  • R 1 and R 2 are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro group; C 6 ⁇ C 60 aryl group; Fluorenyl group; O, N, S, Si, and C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of P; C 3 ⁇ C 60 aliphatic ring group; C 1 ⁇ C 30 alkyl group; C 2 ⁇ C 30 Alkenyl group; Alkynyl group of C 2 to C 30 ; An alkoxyl group of C 1 to C 30 ; C 6 ⁇ C 30 aryloxy group; And it is selected from the group consisting of -L'-N (R a ) (R b ), and neighboring groups may be bonded to each other to form a ring.
  • a is an integer of 0 to 6
  • b is an integer of 0 to 4
  • the aryl group is preferably a C 6 to C 30 aryl group, more preferably a C 6 to C 18 aryl group such as phenyl, naphthyl, biphenyl, Terphenyl, etc.
  • L' is independently a single bond; C 6 ⁇ C 60 arylene group; Fluorenylene group; O, N, S, Si, and C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of P; C 3 ⁇ C 60 aliphatic ring group; And it may be selected from the group consisting of a combination thereof.
  • R a and R b are each independently a C 6 ⁇ C 60 aryl group; Fluorenyl group; O, N, S, Si, and C 2 ⁇ C 60 heterocyclic group containing at least one heteroatom of P; And C 3 ⁇ C 60 It may be selected from the group consisting of an aliphatic ring group.
  • the L 1 ⁇ L 3 , Ar 1 , Ar 2 , R 1 , R 2 , and the rings formed by bonding of adjacent groups to each other are each deuterium; halogen; A silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Siloxane group; Boron group; Germanium group; Cyano group; Nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; A C 6 -C 20 aryloxy group; C 6 -C 20 arylthio group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; Alkynyl group of C 2 -C 20 ; C 6 -C 20 aryl group; Fluorenyl group; O, N, S, Si, and C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of P
  • Formula 1 may be represented by Formula 1-1 or Formula 1-2 below.
  • Y, L 1 to L 3 , Ar 1 , R 1 , R 2 , a, b are the same as defined in Formula 1, and X 1 to X 8 are independently of each other C, is CR or N, at least one of X 1 ⁇ X 8 is N, one of X 1 ⁇ X 8 is C.
  • R is hydrogen, deuterium; halogen; Cyano group; Nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; A C 6 -C 20 aryloxy group; C 6 -C 20 arylthio group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; Alkynyl group of C 2 -C 20 ; C 6 -C 20 aryl group; Fluorenyl group; O, N, S, Si, and C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of P; C 3 -C 20 aliphatic ring group; A C 7 -C 20 arylalkyl group; And C 8 -C 20 is selected from the group consisting of an arylalkenyl group.
  • Formula 1 may be represented by one of Formulas 1-3 to 1-6 below.
  • Y, L 1 to L 2 , Ar 1 , R 1 , R 2 , a, b are as defined in Formula 1, and L 4 is C 6 to C 60 Arylene group; Or O, N, S, Si, and a heterocyclic group of C 2 ⁇ C 60 containing at least one heteroatom of P; and, X 1 to X 8 are each independently C, CR or N, and X 1 to At least one of X 8 is N, and one of X 1 to X 8 is C.
  • R is hydrogen, deuterium; halogen; Cyano group; Nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; A C 6 -C 20 aryloxy group; C 6 -C 20 arylthio group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; Alkynyl group of C 2 -C 20 ; C 6 -C 20 aryl group; Fluorenyl group; O, N, S, Si, and C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of P; C 3 -C 20 aliphatic ring group; A C 7 -C 20 arylalkyl group; And C 8 -C 20 is selected from the group consisting of an arylalkenyl group.
  • Formula 1 may be represented by one of Formulas 1-7 to 1-16 below.
  • Y, L 1 to L 2 , Ar 1 , R 1 , R 2 , a, b are the same as defined in Formula 1, and L 4 is C 6 to C 60 Arylene group; Or O, N, S, Si, and a heterocyclic group of C 2 ⁇ C 60 containing at least one heteroatom of P; and, X 1 to X 8 are each independently C, CR or N, and X 1 to At least one of X 8 is N, and one of X 1 to X 8 is C.
  • R is hydrogen, deuterium; halogen; Cyano group; Nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; A C 6 -C 20 aryloxy group; C 6 -C 20 arylthio group; A C 1 -C 20 alkyl group; An alkenyl group of C 2 -C 20 ; Alkynyl group of C 2 -C 20 ; C 6 -C 20 aryl group; Fluorenyl group; O, N, S, Si, and C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of P; C 3 -C 20 aliphatic ring group; A C 7 -C 20 arylalkyl group; And C 8 -C 20 is selected from the group consisting of an arylalkenyl group.
  • the compound represented by Formula 1 may be one of the following compounds, but is not limited thereto.
  • the present invention provides an organic electric device including an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer includes the compound represented by Formula 1 above.
  • the present invention provides an organic electric device including an anode, a cathode, an organic material layer formed between the anode and the cathode, and a light efficiency improvement layer.
  • the light efficiency improvement layer is formed on one side of both surfaces of the anode or the cathode that is not in contact with the organic material layer, and the organic material layer or the light efficiency improvement layer includes the compound represented by Formula 1 above.
  • the organic material layer includes at least one of a hole injection layer, a hole transport layer, a light emission auxiliary layer, a light emission layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, and preferably the compound may be included in the emission layer.
  • the organic material layer may include two or more stacks including a hole transport layer, an emission layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generation layer formed between the two or more stacks.
  • the present invention provides an electronic device including a display device including an organic electric element represented by Formula 1 and a control unit for driving the display device.
  • the compound (final product) represented by Formula 1 according to the present invention may be synthesized by reacting Sub-1 and Sub-2 as shown in Scheme 1 below, but is not limited thereto.
  • Core 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below, but is not limited thereto.
  • the compound belonging to Core 1 may be the following compound, but is not limited thereto, and Table 1 shows the FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.
  • N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4 -Diamine (hereinafter abbreviated as "2-TNATA”) film was vacuum-deposited to form a hole injection layer with a thickness of 60 nm, and then N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl- (1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as "NPB”) was vacuum deposited to a thickness of 60 nm to form a hole transport layer.
  • 2-TNATA N1,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl- (1,1'-biphenyl)-4,4'-diamine
  • the compound P-1 of the present invention as a host material, bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter, abbreviated as "(piq) 2 Ir(acac)") as a dopant
  • a light emitting layer having a thickness of 30 nm was deposited by doping with a dopant so that the weight ratio was 95:5.
  • BAlq (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum
  • Alq 3 tris(8-quinolinol)aluminum
  • LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer
  • Al was deposited on the electron injection layer to a thickness of 150 nm to form a cathode.
  • An organic electroluminescent device was manufactured 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.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Comparative Compound 1 or Comparative Compound 2 was used as a host material.
  • Comparing Comparative Compound 1 and the compound of the present invention there is a difference in the substituent group bonded to the triazine. That is, the compound of the present invention necessarily has a 4-condensed ring containing S or O bonded to the triazine, whereas Comparative Compound 1 has a simple aryl group (naphthalene) bonded thereto. Therefore, the compound of the present invention has a higher HOMO value than Comparative Compound 1, so that holes are more easily injected into the emission layer, thereby improving the driving voltage, and the compound of the present invention in which the 4-condensed ring is introduced has a significantly narrower band gap. The efficiency also seems to have improved significantly.
  • Comparative Compound 2 when comparing Comparative Compound 2 and the compound of the present invention, Comparative Compound 2 has a triazine bonded to a phenyl (simple aryl group), whereas the compound of the present invention has at least one of Ar 1 and Ar 2 of Formula 1 Since it is a 2-condensed ring containing N, there is a difference in that such a substituent is bonded to the triazine.
  • the LUMO value of the compound of the present invention is deeper than that of Comparative Compound 2, electrons are more easily injected into the light emitting layer, resulting in faster driving, and improved charge blance of holes and electrons, thereby exhibiting a high lifespan.
  • the compound of the present invention has a narrow band gap and excellent hole and electron mobility, so when it is used as a host, the driving voltage of the device is improved, and efficiency and lifespan are increased.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Optics & Photonics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne : un composé représenté par la formule chimique 1 ; un élément électrique organique comprenant une première électrode, une seconde électrode et une couche organique entre la première électrode et la seconde électrode ; et un dispositif électronique comprenant l'élément électrique organique. La couche organique comprend le composé représenté par la formule chimique 1, et ainsi la présente invention peut abaisser la tension de commande de l'élément électronique organique et augmenter l'efficacité lumineuse et la durée de vie de celui-ci.
PCT/KR2020/010341 2019-08-14 2020-08-05 Composé pour élément électronique organique, élément électronique organique l'utilisant, et dispositif électronique associé WO2021029598A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113429353A (zh) * 2021-06-25 2021-09-24 上海钥熠电子科技有限公司 含萘啶衍生物的化合物及其应用
CN115745962A (zh) * 2022-11-14 2023-03-07 浙江虹舞科技有限公司 一种稠合杂环类化合物及其应用以及包含该化合物的有机电致发光器件
US20230301182A1 (en) * 2020-05-12 2023-09-21 Shaanxi Lighte Optoelectronics Material Co., Ltd. Organic compound, and electronic element and electronic device using same

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102545206B1 (ko) * 2019-10-22 2023-06-20 주식회사 엘지화학 신규한 화합물 및 이를 이용한 유기발광 소자
CN116217557A (zh) * 2021-12-02 2023-06-06 常州强力昱镭光电材料有限公司 含二苯并呋喃的化合物和有机电致发光元件
WO2024071841A1 (fr) * 2022-09-29 2024-04-04 주식회사 엘지화학 Nouveau composé et dispositif électroluminescent organique le comprenant

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108003143A (zh) * 2017-12-04 2018-05-08 吉林奥来德光电材料股份有限公司 一种有机发光化合物及其制备方法和有机电致发光器件
CN108003865A (zh) * 2017-12-04 2018-05-08 吉林奥来德光电材料股份有限公司 有机发光化合物及其制备方法和有机电致发光器件
KR20190002206A (ko) * 2017-06-29 2019-01-08 주식회사 엘지화학 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
KR20190045435A (ko) * 2017-10-23 2019-05-03 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
CN109879812A (zh) * 2019-04-22 2019-06-14 吉林奥来德光电材料股份有限公司 蒽类有机发光化合物及其制备方法和应用

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190002206A (ko) * 2017-06-29 2019-01-08 주식회사 엘지화학 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자
KR20190045435A (ko) * 2017-10-23 2019-05-03 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
CN108003143A (zh) * 2017-12-04 2018-05-08 吉林奥来德光电材料股份有限公司 一种有机发光化合物及其制备方法和有机电致发光器件
CN108003865A (zh) * 2017-12-04 2018-05-08 吉林奥来德光电材料股份有限公司 有机发光化合物及其制备方法和有机电致发光器件
CN109879812A (zh) * 2019-04-22 2019-06-14 吉林奥来德光电材料股份有限公司 蒽类有机发光化合物及其制备方法和应用

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20230301182A1 (en) * 2020-05-12 2023-09-21 Shaanxi Lighte Optoelectronics Material Co., Ltd. Organic compound, and electronic element and electronic device using same
US11910709B2 (en) * 2020-05-12 2024-02-20 Shaanxi Lighte Optoelectronics Material Co., Ltd. Organic compound, and electronic element and electronic device using same
CN113429353A (zh) * 2021-06-25 2021-09-24 上海钥熠电子科技有限公司 含萘啶衍生物的化合物及其应用
CN115745962A (zh) * 2022-11-14 2023-03-07 浙江虹舞科技有限公司 一种稠合杂环类化合物及其应用以及包含该化合物的有机电致发光器件

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