WO2021020799A1 - Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique comprenant ledit élément électrique organique - Google Patents

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

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WO2021020799A1
WO2021020799A1 PCT/KR2020/009628 KR2020009628W WO2021020799A1 WO 2021020799 A1 WO2021020799 A1 WO 2021020799A1 KR 2020009628 W KR2020009628 W KR 2020009628W WO 2021020799 A1 WO2021020799 A1 WO 2021020799A1
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aryl
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박종광
이남걸
이선희
문성윤
김정석
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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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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 electric 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, and when the efficiency is increased, the driving voltage decreases relatively, and as the driving voltage decreases, crystallization of organic materials by Joule heating generated during driving decreases. It shows a tendency to increase the lifespan.
  • simply improving the organic material layer cannot maximize efficiency. This is because the long life and high efficiency can be achieved at the same time when the energy level and T1 value between the organic material layers, the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined.
  • 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, thereby generating excitons through recombination.
  • the color purity and efficiency of the organic electronic device are deteriorated, and the lifespan is shortened. Therefore, it must be a material having a HOMO level between the HOMO energy level of the hole transport layer and the HOMO energy level of the light emitting layer, has a high T1 value, and has a suitable driving voltage range (within the driving voltage range of the blue device of the full device). Mobility) is required to develop an auxiliary light emitting layer.
  • the low glass transition temperature of the light emitting layer and the light emitting auxiliary layer material decreases the uniformity of the thin film surface when the device is driven, and the material may be deformed due to heat generated when the device is driven.
  • a material that can withstand a long time during deposition that is, a material with strong heat resistance
  • materials that form the organic material layer in the device such as hole injection material, hole transport material, and light emission, are required to fully exhibit the excellent characteristics of organic electronic devices.
  • a material, an electron transport material, an electron injection material, a light-emitting auxiliary layer material, etc. must be supported by a stable and efficient material. In particular, development of materials used for a light-emitting auxiliary layer and a light-emitting layer is required.
  • 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 and fluorenylene group used in the present invention mean a substituted or unsubstituted fluorenyl group and a substituted unsubstituted fluorenylene group, respectively, unless otherwise specified, and R and R'includes a compound formed by bonding to each other.
  • Unsubstituted fluorenyl group or unsubstituted fluorenylene group refers to a monovalent or divalent functional group in which R, R'and R" are all hydrogen in the following structure, and a substituted fluorenyl group or substituted fluorenylene group In the following structure, it means that at least one of R, R', and R" is a substituent other than hydrogen.
  • a fluorenyl group, a fluorenylene group, and the like 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 means a ring of 3 to 60, but is not limited thereto.
  • a compound in which benzene as an aromatic ring and cyclohexane, which is a non-aromatic ring, are fused is also an aliphatic ring.
  • group name' such as an aryl group, an arylene group, and a heterocyclic group as used herein may describe the'name of the group reflecting the number', but may also be described as the'parent compound name'.
  • 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 pyrimidinyl group and in the case of divalent, pyrimidinylene. 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 210 or a light emission auxiliary layer 220 may be further formed between the hole transport layer 130 and the emission 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, the light emitting auxiliary layer 220 ) And/or the light efficiency improvement layer 180 may be used as a material.
  • 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 layer 140, 340, 440, the light emitting auxiliary layer 220, and/or the light efficiency improvement layer 180, the energy level and T 1 between each organic material layer
  • the value and intrinsic properties of the material it is possible to simultaneously improve the life and efficiency of organic electric devices.
  • 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 prepared 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 prepared 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 may be a top emission type, a bottom emission type, or a double-sided 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).
  • R 1 to R 5 are each independently hydrogen; heavy hydrogen; halogen; Cyano group; Nitro 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; C 6 ⁇ C 30 arylthio group; L 1 -Ar 1 ; And L 2 -N (L 3 -Ar 2 ) (L 4 -Ar 3 ) It is selected from the group consisting of, neighboring groups may be bonded to each other to selectively form a ring.
  • the ring formed by bonding adjacent groups to each other is an aromatic ring group of C 6 ⁇ C 60 ; 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.
  • aromatic ring preferably a C 6 ⁇ C 20 aromatic ring, more preferably a C 6 ⁇ C 14 aromatic ring, such as benzene, naphthalene, phenanthrene, etc. , It can form a ring containing a benzene moiety.
  • heterocycle preferably a C 2 to C 30 heterocyclic group containing at least one heteroatom of O, N, S, more preferably O, N , S C 2 ⁇ C 20 heterocyclic group containing at least one heteroatom, such as indole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, heterocycle containing a carbazole moiety, etc.
  • a C 2 to C 30 heterocyclic group containing at least one heteroatom of O, N, S more preferably O, N , S C 2 ⁇ C 20 heterocyclic group containing at least one heteroatom, such as indole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, heterocycle containing a carbazole moiety, etc.
  • a C 3 to C 30 aliphatic ring group preferably a C 3 to C 20 aliphatic ring group, such as 2,3 -Dihydro-1,1-dimethyl-1 H -may be indene.
  • a and e are each an integer of 0 to 4
  • b is an integer of 0 to 3
  • c and d are each an integer of 0 to 2
  • Each of R 4 and each of R 5 are the same as or different from each other.
  • L 1 to L 4 is 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.
  • L 1 is an arylene group, preferably a C 6 ⁇ C 30 arylene group, more preferably a C 6 ⁇ C 18 arylene group, such as phenylene, biphenylene, naphthalene, terphenyl, etc. .
  • L 1 is a heterocyclic group, preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 23 heterocyclic group, such as pyridine, pyrimidine, triazine, quinoline, isoquinoline , Quinazoline, benzoquinazoline, dibenzoquinazoline, quinoxaline, dibenzofuran, dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine, benzofuropyrazole, benzimidazole, carbazole , Phenylcarbazole, spiro[fluorene-9,9'-indenopyrimidine], and the like.
  • pyridine pyrimidine
  • triazine such as pyridine, pyrimidine, triazine, quinoline, isoquinoline , Quinazoline, benzoquinazoline, dibenzoquinazoline, quinoxaline, dibenzofuran, dibenzothiophene, be
  • L 2 to L 4 is an arylene group, preferably a C 6 to C 30 arylene group, more preferably a C 6 to C 18 arylene group such as phenylene, biphenylene, naphthalene, terphenyl Etc.
  • the L 2 to L 4 is a heterocyclic group, preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 12 heterocyclic group such as dibenzofuran, dibenzothiophene, It may be carbazole and the like.
  • the L 2 to L 4 is a fluorenyl group
  • it may be 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, and the like.
  • Ar 1 to Ar 3 are each independently a C 6 to 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.
  • Ar 1 to Ar 3 are an aryl group, 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, phenanthrene , Pyrene, anthracene, and the like.
  • Ar 1 to Ar 3 are fluorenyl groups, 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[ Benzo[ b ]fluorene-11,9'-fluorene], benzo[ b ]fluorene, 11,11-diphenyl-11 H -benzo[ b ]fluorene, 9-(naphthalen-2-yl)9 -phenyl -9 H-fluorene, and the like.
  • Ar 1 to Ar 3 is a heterocyclic group, preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 25 heterocyclic group such as pyrimidine, triazine, quinoline, isoquinoline, Quinazoline, benzoquinazoline, dibenzoquinazoline, quinoxaline, benzothienopyrimidine, benzofuropyrimidine, benzofuropyrazole, benzimidazole, carbazole, phenylcarbazole, spiro[fluorene -9,9'-indenopyrimidine], naphthobenzofuran, naphthobenzothiophene, benzocarbazole, benzophenylcarbazole, spiro[fluorene-9,9'-xanthene], and the like.
  • pyrimidine triazine
  • quinoline isoquinoline
  • Quinazoline benzoquinazoline
  • dibenzoquinazoline quinox
  • the R 1 to R 5 , L 1 to L 4 , Ar 1 to Ar 3 , and the rings formed by bonding of adjacent groups to each other are deuterium, respectively; halogen; A silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Phosphine oxide 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; Fluor
  • Formula 1 may be represented by one of Formulas 1-1 to 1-5 below.
  • R 1 to R 5 a to e, L 1 and Ar 1 are the same as defined in Formula 1 above.
  • Formula 1 may be represented by one of Formulas 1-6 to 1-10 below.
  • R 1 to R 5 , a to e, L 2 to L 4 , Ar 2 and Ar 3 are the same as defined in Chemical Formula 1.
  • X 1 and X 2 are each independently a single bond, C(R')(R"), N-(L 5 -Ar 4 ), O or S, except when both X 1 and X 2 are single bonds do.
  • R 6 , R 7 , R'and R" are each independently hydrogen; deuterium; halogen; a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; C 1 -C 20 Phosphine oxide unsubstituted or substituted with an alkyl group of or 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 an alkoxy group; alkynyl of C 2 -C 20; C 6 -C 20 aryloxy; C 6 -C 20 aryl import of Im; C 2 -C 20 alkenyl group of; C 1 -C 20 alkyl group; C 6 -C 20 aryl group; fluorenyl group; C 2 -C 20 heterocyclic group including at least one heteroatom selected from the group
  • f is an integer of 0 to 4, when f is an integer of 2 or more, each of R 6 is the same as or different from each other, g is an integer of 0 to 2, and when g is an integer of 2, each of R 7 is the same or different from each other.
  • L 5 is a single bond; 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; And C 3 -C 20 It may be selected from the group consisting of an aliphatic ring group.
  • Ar 4 is a 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; And C 3 -C 20 It may be selected from the group consisting of an aliphatic ring group.
  • At least one of R 1 to R 5 in Formula 1 is selected from the group consisting of a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a carbazolyl group, the following formula B-1, the following formula B-2, and the following formula B-3 Can be.
  • L is defined in the same manner as L 1 of claim 1, and Y 1 to Y 16 are each independently C (R c ) or N, and X 3 and X 4 are each Independently, it is a single bond, C(R d )(R e ), N-(L 5 -Ar 4 ), O or S, except when both X 3 and X 4 are single bonds.
  • R c , R d and R e are each independently hydrogen; heavy hydrogen; halogen; A silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Phosphine oxide 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 heterocycl
  • L 5 is a single bond; 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; And C 3 -C 20 It may be selected from the group consisting of an aliphatic ring group.
  • Ar 4 is a 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; And C 3 -C 20 It may be selected from the group consisting of an aliphatic ring group.
  • At least one of Ar 2 and Ar 3 in Formula 1 may be represented by the following Formula C.
  • L 7 is defined the same as L 1 in Formula 1, and ring A and ring B are independently of each other C 6 ⁇ C 20 aromatic ring group or at least one of O, N, S, Si and P It is a C 4 ⁇ C 20 heterocyclic group containing a hetero atom of, and X 5 is C(R')(R"), N-(L 5 -Ar 4 ), O or S.
  • the R′ and R” are independently of each other hydrogen; deuterium; halogen; a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; a siloxane group; a boron group; a germanium group; a cyanide group; group; a C 1 -C 20; a nitro group; C 1 -C 20 coming of the alkylthio; C 1 -C 20 alkoxy group; Im coming aryl of C 6 -C 20; C 6 -C 20 aryloxy group Alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkynyl group; C 6 -C 20 aryl group; fluorenyl group; at least one selected from the group consisting of O, N, S, Si and P C 2 -C 20 heterocyclic group including a hetero atom; C 3 -C 20 aliphatic ring group
  • L 5 is a single bond; 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; And C 3 -C 20 It may be selected from the group consisting of an aliphatic ring group.
  • Ar 4 is a 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; And C 3 -C 20 It may be selected from the group consisting of an aliphatic ring 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 electrical device comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode, wherein the organic material layer is one single compound or two or more Contains compounds.
  • 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 emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, and preferably, the compound is included in the emission layer and/or the emission auxiliary layer. Can be included.
  • 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 or Sub 1 and Sub 3 as shown in Scheme 1 below, but is not limited thereto.
  • Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below, but is not limited thereto.
  • the compounds belonging to Sub 1 may be the following compounds, but are not limited thereto, and Table 1 shows the FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.
  • Sub 2 of Scheme 1 may be synthesized by the reaction route of Scheme 3 below, but is not limited thereto.
  • the compound belonging to Sub 2 may be the following compound, but is not limited thereto, and Table 2 shows the FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.
  • Bpin is boronic acid pinacol ester, Means ).
  • Sub 3 of Scheme 1 may be synthesized by the reaction path of Scheme 4 below (initiated in Korean Patent Registration No. 10-1251451 (published on April 5, 2013)), but is not limited thereto.
  • the compound belonging to Sub 3 may be the following compound, but is not limited thereto, and Table 3 shows the FD-MS 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 having 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
  • compound 1-1 of the present invention is used as a host material, and bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter abbreviated as "(piq) 2 Ir(acac)”) is used 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 5 was used instead of the compound 1-1 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 A or Comparative Compound B was used as a host material.
  • the compounds represented by Formula 1 of the present invention condensate one more benzene ring, resulting in a deeper T1 level (a smaller value), and energy transfer to a dopant.
  • the luminous efficiency seems to be greatly improved.
  • the compound of the present invention has increased planarity and a high Tg value compared to the comparative compounds, and thus the lifespan seems to be significantly improved.
  • Example 16 Red organic electroluminescent device ( Light-emitting auxiliary layer )
  • a 2-TNATA film was vacuum-deposited on the ITO layer (anode) formed on the glass substrate to form a hole injection layer with a thickness of 60 nm, and then NPB was vacuum evaporated to form a hole transport layer having a thickness of 60 nm. Subsequently, the compound 1-75 of the present invention was vacuum-deposited to a thickness of 20 nm on the hole transport layer to form a light emission auxiliary layer.
  • CBP 4,4'-N,N'-dicarbazole-biphenyl
  • Ir acac
  • Dopant was doped so that the weight ratio was 95:5 to form a light emitting layer having a thickness of 30 nm.
  • BAlq was vacuum deposited on the emission layer to a thickness of 10 nm to form a hole blocking layer
  • Alq 3 was deposited on the hole blocking layer 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 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 16, except that the compound of the present invention described in Table 6 was used instead of the compound of the present invention 1-75 as the light emitting auxiliary layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example 16, except that the light emission auxiliary layer was not formed.
  • An organic electroluminescent device was manufactured in the same manner as in Example 16, except that Comparative Compounds 3 to 5 below were used instead of Compound 1-75 of the present invention as a material for the auxiliary layer.
  • electroluminescence (EL) characteristics were measured with a PR-650 of Photoresearch, and 2500 cd/m 2 At the reference luminance, the T95 life was measured with a life measurement equipment manufactured by McScience. The measurement results are shown in Table 6 below.
  • the device result was superior when one of Comparative Compounds 3 to 5 (Comparative Examples 4 to 6) was used rather than when the light emission auxiliary layer was not formed (Comparative Example 3), Compared to Comparative Examples 4 to 6, the driving voltage of the device in which the compound of the present invention is used as a light emitting auxiliary layer material is lower, and efficiency and lifespan are significantly improved.

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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 placée entre la première électrode et la seconde électrode ; et un dispositif électronique comprenant l'élément électrique organique. Le composé représenté par la formule chimique 1 est contenu dans la couche organique, l'élément électrique organique pouvant ainsi avoir une faible tension de commande, une efficacité lumineuse améliorée et une durée de vie accrue.
PCT/KR2020/009628 2019-07-30 2020-07-22 Composé pour élément électrique organique, élément électrique organique l'utilisant, et dispositif électronique comprenant ledit élément électrique organique WO2021020799A1 (fr)

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