WO2021033970A1 - Compound for organic electronic element, organic electronic element using same, and electronic device thereof - Google Patents

Compound for organic electronic element, organic electronic element using same, and electronic device thereof Download PDF

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WO2021033970A1
WO2021033970A1 PCT/KR2020/010424 KR2020010424W WO2021033970A1 WO 2021033970 A1 WO2021033970 A1 WO 2021033970A1 KR 2020010424 W KR2020010424 W KR 2020010424W WO 2021033970 A1 WO2021033970 A1 WO 2021033970A1
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group
formula
layer
heteroatom
independently
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김창겸
박형근
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
    • 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
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09G—ARRANGEMENTS OR CIRCUITS FOR CONTROL OF INDICATING DEVICES USING STATIC MEANS TO PRESENT VARIABLE INFORMATION
    • G09G3/00—Control arrangements or circuits, of interest only in connection with visual indicators other than cathode-ray tubes
    • G09G3/20—Control arrangements or circuits, of interest only in connection with visual indicators other than cathode-ray tubes for presentation of an assembly of a number of characters, e.g. a page, by composing the assembly by combination of individual elements arranged in a matrix no fixed position being assigned to or needed to be assigned to the individual characters or partial characters
    • G09G3/22—Control arrangements or circuits, of interest only in connection with visual indicators other than cathode-ray tubes for presentation of an assembly of a number of characters, e.g. a page, by composing the assembly by combination of individual elements arranged in a matrix no fixed position being assigned to or needed to be assigned to the individual characters or partial characters using controlled light sources
    • G09G3/30—Control arrangements or circuits, of interest only in connection with visual indicators other than cathode-ray tubes for presentation of an assembly of a number of characters, e.g. a page, by composing the assembly by combination of individual elements arranged in a matrix no fixed position being assigned to or needed to be assigned to the individual characters or partial characters using controlled light sources using electroluminescent panels
    • G09G3/32—Control arrangements or circuits, of interest only in connection with visual indicators other than cathode-ray tubes for presentation of an assembly of a number of characters, e.g. a page, by composing the assembly by combination of individual elements arranged in a matrix no fixed position being assigned to or needed to be assigned to the individual characters or partial characters using controlled light sources using electroluminescent panels semiconductive, e.g. using light-emitting diodes [LED]
    • G09G3/3208—Control arrangements or circuits, of interest only in connection with visual indicators other than cathode-ray tubes for presentation of an assembly of a number of characters, e.g. a page, by composing the assembly by combination of individual elements arranged in a matrix no fixed position being assigned to or needed to be assigned to the individual characters or partial characters using controlled light sources using electroluminescent panels semiconductive, e.g. using light-emitting diodes [LED] organic, e.g. using organic light-emitting diodes [OLED]
    • 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, which has been reported to have a great effect on the life of the device.
  • 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 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 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 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).
  • R 1 to R 4 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 -LN (R a ) (R b ), and neighboring groups may be bonded to each other to selectively form a ring.
  • a and b are each an integer of 0 to 2
  • c and d are each an integer of 0 to 3 and when each is an integer of 2 or more, each of R 1, each of R 2, each of R 3, and each of R 4 is the same or different from each other Do.
  • 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.
  • 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.
  • the heterocycle is preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 18 heterocyclic group such as triazine, quina It may be sleepy, benzoquinazoline, dibenzothiophene, dibenzofuran, naphthobenzofuran, naphthobenzothiophene, carbazole, phenylcarbazole, and the like.
  • the alkyl group is preferably a C 1 to C 10 alkyl group, such as methyl or t-butyl.
  • L 1 and L 2 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 an arylene group of C 6 to C 30 , more preferably an arylene group of C 6 to C 18 such as phenylene, naphthylene, It may be biphenylene, terphenyl, and the like.
  • the heterocycle is preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 18 heterocyclic group, such as pyridine, pyrimidine , Triazine, pyrazine, carbazole, phenylcarbazole, quinazoline, benzoquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, quinoline, isoquinoline, benzoquinoline, benzothienopyrimidine, benzofuro Pyrimidine, dibenzodioxin, phenothiazine, phenoxatin, benzoimidazole, benzothiazole, indole, benzoxazole, dibenzothiophene, dibenzofuran, and the like.
  • pyridine pyrimidine
  • Triazine pyrazine
  • carbazole phenylcarbazole
  • quinazoline benzoquinazoline
  • quinoxaline quinoxaline
  • Ar 1 and Ar 2 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; C 3 ⁇ C 60 aliphatic ring group; And -LN(R a ) (R b ) It may be selected from the group consisting of.
  • 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, phenanthrene, triphenylene, pyrene, chrysene, anthracene, and the like.
  • the heterocycle is preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 22 heterocyclic group, such as pyridine, pyrimidine , Triazine, pyrazine, carbazole, phenylcarbazole, phenylbenzocarbazole, quinazoline, benzoquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, quinoline, isoquinoline, benzoquinoline, benzothienopyr Midine, benzofuropyrimidine, dibenzodioxin, phenothiazine, phenoxatin, benzoimidazole, benzothiazole, indole, benzoxazole, dibenzothiophene, dibenzofuran, naphthobenzothiophene, naphtho It may be benzofuran and the like.
  • pyridine pyrimidine
  • Triazine pyrazine
  • the fluorenyl group is 9,9-dimethyl-9 H -fluorene, 9,9-diphenyl-9 H -fluorenyl group, 9,9 '- may be spyrobifluorene or the like.
  • the aliphatic ring group is preferably an aliphatic ring group of C 3 to C 30 , more preferably an aliphatic ring group of C 3 to C 10 such as cyclohexane, a It may be Damantil.
  • L is 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.
  • the arylene group is preferably a C 6 ⁇ C 30 arylene group, more preferably a C 6 ⁇ C 18 arylene group, such as phenylene, naphthylene, biphenylene, terphenyl, etc. I can.
  • 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 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.
  • the heterocycle is preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 12 heterocyclic group, such as dibenzothiophene , Dibenzofuran, and the like.
  • R a and R b are fluorenyl groups
  • the fluorenyl group is 9,9-dimethyl-9 H -fluorene, 9,9-diphenyl-9 H -fluorenyl group, 9,9 '- may be spyrobifluorene or the like.
  • the R 1 ⁇ R 4 , L 1 , L 2 , Ar 1 , Ar 2 , and the rings formed by bonding of neighboring 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; 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; Flu
  • Formula 1 may be represented by one of Formulas 1-1 to 1-6 below.
  • R 1 to R 4 , a to d, L 1 , L 2 , Ar 1 , Ar 2 , L, R a , R b are as defined in Formula 1.
  • Formula 1 may be represented by one of Formulas 2-1 to 2-6 below.
  • R 1 to R 4 , a to d, L 1 , L 2 , Ar 1 , Ar 2 are the same as defined in Formula 1, and L 6 is 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 is selected from the group consisting of, X 1 ⁇ X 6 is independently C, C (R ') or N to each other, and at least one of X 1 ⁇ X 6 is N, X one of 1 ⁇ X 6 Is C.
  • R' is independently of each other 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; Cyano group; Nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; A C 6 -C 20 aryloxy 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 arylalkenyl group, neighboring groups may be bonded
  • the L 1 , L 2 and L may be independently selected from the group consisting of the following Formulas b-1 to b-13.
  • Z is O, S, N-(L'-Ar') or C(R')(R"), and Z 49 to Z 51 are each independently C, is C (R ') or N, Z 49 to Z 51, at least one of is N, Z 49 to Z 51 are C, at least one way.
  • R 5 to R 7 wherein 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; a cyano group; nitro group; a C 2 -C 20 alkenyl;; C 1 -C 20 alkylthio Sy of; C 1 -C 20 alkoxy group; C 6 -C 20 aryloxy; C 1 -C 20 alkyl C 2 -C 20 alkynyl group; C 6 -C 20 aryl group; fluorenyl group; C 2 -C 20 heterocycle containing at least one hetero atom selected from the group consisting of O, N, S, Si and P Group; C 3 -C 20 aliphatic ring group; C 7 -C 20 arylalkyl group; And C 8 -C 20 selected from the group consisting of arylalkenyl groups, neighbor
  • a", c", d", e", g" is an integer from 0 to 4
  • b" is an integer from 0 to 6
  • f" is an integer from 0 to 3
  • h" is an integer from 0 to 2
  • i is an integer of 0 to 3 and when each of them is an integer of 2 or more, each of R 5, each of R 6, and each of R 7 is the same as or different from each other.
  • Ar' 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 of P; C 3 ⁇ C 20 aliphatic ring group; And it may be selected from the group consisting of a combination thereof.
  • L' is independently a single bond; C 6 ⁇ C 20 arylene group; Fluorenylene group; O, N, S, Si, and C 2 ⁇ C 20 heterocyclic group containing at least one heteroatom 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 a and R b may be represented by the following Formula B-1.
  • ring A and ring B are independently of each other C 6 ⁇ C 20 aromatic ring group or C 4 ⁇ C 20 hetero containing at least one heteroatom of O, N, S, Si and P And Z is O, S, N-(L'-Ar') or C(R')(R").
  • 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 cyano group; a nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; C 6 -C 20 aryloxy group; C 1 -C 20 alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkynyl group ; C 6 -C 20 aryl group; fluorenyl group; C 2 -C 20 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C It is selected from the group consisting of an aliphatic ring group of 20; C 7 -C 20 arylalkyl group; And C 8 -C 20 arylalkenyl group,
  • Ar' 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 of P; C 3 ⁇ C 20 aliphatic ring group; And it may be selected from the group consisting of a combination thereof.
  • L' is independently a single bond; C 6 ⁇ C 20 arylene group; Fluorenylene group; O, N, S, Si, and C 2 ⁇ C 20 heterocyclic group containing at least one heteroatom 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 4 , Ar 1 and Ar 2 may be selected from the group consisting of the following Formulas A-1 to A-6.
  • X 1 -X 6 are each independently C, C(R 1 ) or N, and one of X 1 -X 6 is C bonded to a linking group L. Preferably, at least one of X 1 -X 6 is N.
  • X 1 -X 4 are each independently C, C(R 1 ) or N , one of X 1 -X 4 is C bonded to a linking group L, and Y 1 -Y 4 are independent of each other By C(R 1 ) or N.
  • X 1 -X 4 and Y 1 to Y 4 is N.
  • X 1 -X 6 are independently of each other C, C(R 1 ) or N , one of X 1 -X 6 is C bonded to a linking group L, and Y 1 -Y 4 are independent of each other By C(R 1 ) or N.
  • X 1 -X 6 and Y 1 to Y 4 is N.
  • X 1 -X 4 are each independently C, C(R 1 ) or N , one of X 1 -X 4 is C bonded to a linking group L, and Y 1 -Y 8 are independent of each other By C(R 1 ) or N.
  • X 1 -X 4 and Y 1 -Y 8 is N.
  • X 1 -X 4 are each independently C, C(R 1 ) or N
  • Y 1 -Y 4 are each independently C(R 1 ) or N
  • V and W are independently of each other As O, S, N, N-(L'-Ar'), C(R') or C(R')(R")
  • e and f are each 0 or 1
  • one of X 1 -X 4 is C bonded to the linking group L
  • one of V and W is N or C(R′) bonded to the linking group L.
  • X 1 -X 4 At least one of them is N or/and at least one of V and W is N or N-(L'-Ar').
  • X 1 -X 4 , X 6 are each independently C, C(R 1 ) or N, and Y 1 is O, S, N, N-(L'-Ar'), C( R') or C(R')(R"), and Y 2 is N.
  • one of X 1 -X 4 and X 6 is N or/and Y 1 is N or N-(L'- Ar').
  • the R 1 , 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 cyano group; a nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; C 6 -C 20 aryloxy group; C 1 -C 20 alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 Alkynyl group; C 6 -C 20 aryl group; fluorenyl group; C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C It is selected from the group consisting of 3 -C 20 aliphatic ring group; C 7 -C 20 arylalkyl group; And C 8 -C 20 arylalkenyl
  • Ar' 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 of P; C 3 ⁇ C 20 aliphatic ring group; And it may be selected from the group consisting of a combination thereof.
  • L' is independently a single bond; C 6 ⁇ C 20 arylene group; Fluorenylene group; O, N, S, Si, and C 2 ⁇ C 20 heterocyclic group containing at least one heteroatom 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 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.
  • 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 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.
  • 1,8-dibromonaphthalene 50 g, 174.8 mmol was added to a round bottom flask and dissolved in 350 mL of THF, followed by (2-nitrophenyl)boronic acid (29.2 g, 174.8 mmol), Pd(PPh 3 ) 4 (6.1 g, 5.3 mmol), NaOH (21 g, 524.5 mmol), and 175 mL of water were added, followed by stirring at 80°C.
  • the reaction was completed, the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 40.7 g (yield: 71%) of the product.
  • Sub 1-III-1 (24.9 g, 81.3 mmol), NaCl (8.1 g, 203.2 mmol), and AlCl 3 (54.2 g, 406.4 mmol) were dissolved in benzene, and the melt was hydrolyzed.
  • the benzene solution was washed with NaHCO 3 aqueous solution and water, dried over MgSO 4 , concentrated, and dissolved with a small amount of high-temperature p-xylene. Then, after separation by silica gel column, the product was recrystallized with methylcyclohexane to obtain 9.2 g (yield: 37%).
  • Sub 1-IV-1 (9.3 g, 30.6 mmol) was added to a round bottom flask and dissolved with toluene (100 mL), followed by iodobenzene (6.2 g, 30.6 mmol), Pd 2 (dba) 3 (0.8 g, 0.9 mmol) , P( t- Bu) 3 (0.4 g, 1.8 mmol), NaO t- Bu (8.8 g, 91.7 mmol) was added and stirred at 100°C. After completion of the reaction, the organic layer extracted with CH 2 Cl 2 and water was dried over MgSO 4 and concentrated with an evaporator. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 7.7 g (yield: 66%) of the product.
  • 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.
  • the compound belonging to Sub 2 of Scheme 1 may be a compound as follows, but is not limited thereto, and Table 2 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 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
  • the compound P-11 of the present invention as a host material on the hole transport layer, 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 94:6.
  • 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 4 was used instead of the compound of the present invention P-11 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 instead of Compound P-11 of the present invention as a host material.
  • the compounds of the present invention are structurally different from Comparative Compounds 1 and 2 in that the two carbazole moieties are a core condensed on the middle 7-membered ring. Due to these differences, the compounds of the present invention have improved hole properties and band gap. This narrowing seems to improve driving voltage and efficiency. In addition, the compound of the present invention has increased planarity and a high Tg value compared to the comparative compound, and thus the lifespan is also remarkably improved.
  • 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.
  • 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 18, except that the light emission auxiliary layer was not formed.
  • An organic electroluminescent device was manufactured in the same manner as in Example 18, except that one of the following Comparative Compounds 3 to 5 was used instead of the compound of the present invention as the light emitting auxiliary layer material.
  • electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch, and 5000 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 5 below.
  • the driving voltage is lowered, the efficiency and lifespan are significantly improved, and in particular, the lifespan is significantly improved.
  • the compound of the present invention to which the pyrrolidine moiety is further introduced has improved hole transport capacity and narrower band gap than Comparative Compounds 3 to 5, and thus luminous efficiency and driving voltage were improved.
  • Tables 4 and 5 are merely illustrative of the present invention, and those of ordinary skill in the art to include other compounds in the light emitting layer within the range not departing from the essential characteristics of the present invention. Various variations are possible, including ways to improve performance.

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Abstract

The present invention provides: a compound represented by chemical formula 1; an organic electronic element comprising a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode; and an electronic device comprising the organic electronic element. The organic layer includes the compound represented by chemical formula 1, and thus the present invention can lower the driving voltage of the organic electronic element and increase the luminous efficiency and lifespan thereof.

Description

유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치Compound for organic electric element, organic electric element using same, and electronic device thereof
본 발명은 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치에 관한 것이다.The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기전기소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기전기소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 등으로 이루어질 수 있다.In general, 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. Here, 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.
유기전기소자에서 유기물층으로 사용되는 재료는 기능에 따라, 발광 재료와 전하수송 재료, 예컨대 정공주입 재료, 정공수송 재료, 전자수송 재료, 전자주입 재료 등으로 분류될 수 있다. 그리고 상기 발광 재료는 분자량에 따라 고분자형과 저분자형으로 분류될 수 있고, 발광 메커니즘에 따라 전자의 일중항 여기상태로부터 유래되는 형광 재료와 전자의 삼중항 여기상태로부터 유래되는 인광 재료로 분류될 수 있다. 또한, 발광 재료는 발광색에 따라 청색, 녹색, 적색 발광 재료와 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 재료로 구분될 수 있다.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. In addition, 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. In addition, 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.
한편, 발광 재료로서 하나의 물질만 사용하는 경우 분자간 상호 작용에 의하여 최대 발광 파장이 장파장으로 이동하고 색순도가 떨어지거나 발광 감쇄 효과로 소자의 효율이 감소되는 문제가 발생하므로, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여 발광 재료로서 호스트/도판트계를 사용할 수 있다. 그 원리는 발광층을 형성하는 호스트보다 에너지 대역 간극이 작은 도판트를 발광층에 소량 혼합하면, 발광층에서 발생한 엑시톤이 도판트로 수송되어 효율이 높은 빛을 내는 것이다. 이때 호스트의 파장이 도판트의 파장대로 이동하므로, 이용하는 도판트의 종류에 따라 원하는 파장의 빛을 얻을 수 있다.On the other hand, when only one material is used as a light-emitting material, the maximum emission wavelength shifts to a long wavelength due to intermolecular interactions, and the color purity decreases or the efficiency of the device decreases due to the emission attenuation effect.Therefore, the increase in color purity and energy transfer 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.
현재 휴대용 디스플레이 시장은 대면적 디스플레이로 그 크기가 증가하고 있는 추세이며, 이로 인해 기존 휴대용 디스플레이에서 요구하던 소비전력보다 더 큰 소비전력이 요구되고 있다. 따라서, 배터리라는 제한적인 전력 공급원을 가지고 있는 휴대용 디스플레이 입장에서는 소비전력이 중요한 요소가 되었고, 효율과 수명 문제 또한 반드시 해결해야 하는 중요한 요소이다.Currently, the portable display market is increasing in size as a large-area display, and for this reason, more power consumption than the power consumption required by the existing portable display is required. Therefore, power consumption has become an important factor for portable displays that have a limited power supply source, such as a battery, and efficiency and life problems are also important factors that must be solved.
효율과 수명, 구동전압 등은 서로 연관이 있으며, 효율이 증가되면 상대적으로 구동전압이 떨어지고, 구동전압이 떨어지면서 구동시 발생되는 주울열(Joule heating)에 의한 유기물질의 결정화가 적어져 결과적으로 수명이 높아지는 경향을 나타낸다. 하지만 상기 유기물층을 단순히 개선한다고 하여 효율을 극대화시킬 수는 없다. 왜냐하면, 각 유기물층 간의 에너지 준위 및 T1 값, 물질의 고유특성(이동도, 계면특성 등) 등이 최적의 조합을 이루었을 때 긴 수명과 높은 효율을 동시에 달성할 수 있기 때문이다.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. However, 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.
또한, 최근 유기 전기 발광소자에 있어 정공수송층에서의 발광 문제를 해결 하기 위해 정공수송층과 발광층 사이에 발광보조층을 사용하는 방법이 연구되고 있으며, 각각의 발광층(R, G, B)에 따라 원하는 물질적 특성이 상이하여, 각각의 발광층에 따른 발광보조층의 개발이 필요한 시점이다.In addition, in recent years, in order to solve the problem of light emission in the hole transport layer in organic electroluminescent devices, a method of using a light emitting auxiliary layer between the hole transport layer and the light emitting layer is being studied, and desired according to each light emitting layer (R, G, B). Since material properties are different, it is time to develop a light emitting auxiliary layer for each light emitting layer.
일반적으로 전자수송층에서 발광층으로 전자(electron)가 전달되고 정공(hole)이 정공수송층에서 발광층으로 전달되어 재조합(recombination)에 의해 엑시톤(exciton)이 생성된다.In general, 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.
하지만, 정공수송층에 사용되는 물질의 경우 낮은 HOMO 값을 가져야 하기 때문에 대부분 낮은 T1 값을 가지며, 이로 인해 발광층에서 생성된 엑시톤(exciton)이 정공수송층 계면 또는 정공수송층쪽으로 넘어가게 되어 결과적으로 정공 수송층 계면에서의 발광 또는 발광층 내 전하 불균형(charge unbalance)을 초래하여 정공수송층 계면에서 발광하게 된다.However, in the case of the material used for the hole transport layer, since it must have a low HOMO value, most have a low T 1 value, and as a result, excitons generated in the light-emitting layer pass to the hole transport layer interface or the hole transport layer, resulting in the hole transport layer. Light emission at the interface or charge unbalance in the light-emitting layer is caused to emit light at the hole transport layer interface.
정공수송층 계면에서 발광될 경우, 유기전기소자의 색순도 및 효율이 저하되고 수명이 짧아지는 문제점이 발생하게 된다. 따라서, 정공수송층 HOMO에너지 준위와 발광층의 HOMO에너지 준위 사이의 HOMO 준위를 갖는 물질이어야 하며, 높은 T1 값을 가지고, 적당한 구동전압 범위 내(full device의 blue 소자 구동전압 범위 내) 정공 이동도(hole mobility)를 갖는 발광보조층의 개발이 요구된다.When light is emitted at the hole transport layer interface, 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.
하지만, 이는 단순히 발광보조층 물질의 코어에 대한 구조적 특성으로 이루어 질 수 없으며, 발광보조층 물질의 코어 및 sub-치환기의 특성 그리고 발광보조층과 정공수송층, 발광보조층과 발광층 간의 알맞은 조합이 이루어졌을 때 고효율 및 고수명의 소자가 구현될 수 있는 것이다.However, this cannot be achieved simply with the structural characteristics of the core of the light-emitting auxiliary layer material, and the characteristics of the core and sub-substituents of the light-emitting auxiliary layer material, and the proper combination between the light-emitting auxiliary layer and the hole transport layer, and the light-emitting auxiliary layer and the light-emitting layer are made When it is lost, a high-efficiency and long-life device can be implemented.
한편, 소자 구동시 발생되는 주울열(Joule heating)에 대해서도 안정된 특성, 즉 높은 유리 전이온도를 갖는 발광층 및 발광보조층 재료에 대한 개발 역시 필요한 상태이다. 발광층층 및 발광보조층 재료의 낮은 유리전이 온도는 소자 구동시 박막 표면의 균일도를 저하시키고, 소자 구동 시 발생하는 열로 인하여 물질이 변형될 수 있으며 이는 소자수명에 큰 영향을 미치는 것으로 보고되고 있다. Meanwhile, development of materials for a light-emitting layer and a light-emitting auxiliary layer having a stable characteristic, that is, a high glass transition temperature, against Joule heating generated when the device is driven is also required. 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, which has been reported to have a great effect on the life of the device.
따라서, 증착시 오랫동안 견딜 수 있는 재료, 즉 내열특성이 강한 재료 개발이 필요하며, 유기전기소자가 갖는 우수한 특징들을 충분히 발휘하기 위해서는 소자 내 유기물층을 이루는 물질, 예컨데 정공주입 물질, 정공수송 물질, 발광 물질, 전자수송 물질, 전자주입 물질, 발광보조층 물질 등이 안정하고 효율적인 재료에 의하여 뒷받침되는 것이 선행되어야 하는데, 특히 발광보조층, 발광층 등에 사용되는 재료에 대한 개발이 요구되고 있다.Therefore, it is necessary to develop a material that can withstand a long time during deposition, that is, a material with strong heat resistance, and 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.
본 발명은 소자의 구동전압을 낮추고, 소자의 발광효율 및 수명을 향상시킬 수 있는 화합물, 이를 이용한 유기전기소자 및 그 전자장치를 제공하는 것을 목적으로 한다.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.
일 측면에서, 본 발명은 하기 화학식으로 표시되는 화합물을 제공한다.In one aspect, the present invention provides a compound represented by the following formula.
Figure PCTKR2020010424-appb-I000001
Figure PCTKR2020010424-appb-I000001
다른 측면에서, 본 발명은 상기 화학식으로 표시되는 화합물을 이용한 유기전기소자 및 그 전자장치를 제공한다.In another aspect, the present invention provides an organic electric device and an electronic device using the compound represented by the above formula.
본 발명의 실시예에 따른 화합물을 이용함으로써 소자의 구동전압을 낮출 수 있을 뿐만 아니라, 소자의 발광효율, 색순도, 안정성 및 수명을 크게 향상시킬 수 있다.By using 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.
도 1 내지 도 3은 본 발명에 따른 유기전기발광소자의 예시도이다.1 to 3 are exemplary views of an organic electroluminescent device according to the present invention.
[부호의 설명][Explanation of code]
100, 200, 300: 유기전기소자 110: 제1 전극100, 200, 300: organic electric device 110: first electrode
120: 정공주입층 130: 정공수송층120: hole injection layer 130: hole transport layer
140: 발광층 150: 전자수송층140: light emitting layer 150: electron transport layer
160: 전자주입층 170: 제2 전극160: electron injection layer 170: second electrode
180: 광효율 개선층 210: 버퍼층180: light efficiency improvement layer 210: buffer layer
220: 발광보조층 320: 제1 정공주입층220: light emission auxiliary layer 320: first hole injection layer
330: 제1 정공수송층 340: 제1 발광층330: first hole transport layer 340: first emission layer
350: 제1 전자수송 층 360: 제1 전하생성층350: first electron transport layer 360: first charge generation layer
361: 제2 전하생성층 420: 제2 정공주입층361: second charge generation layer 420: second hole injection layer
430: 제2 정공수송층 440: 제2 발광층430: second hole transport layer 440: second emission layer
450: 제2 전자수송층 CGL: 전하생성층450: second electron transport layer CGL: charge generation layer
ST1: 제1 스택 ST2: 제2 스택ST1: first stack ST2: second stack
본 발명에서 사용된 용어 "아릴기" 및 "아릴렌기"는 다른 설명이 없는 한 각각 6 내지 60의 탄소수를 가지며, 이에 제한되는 것은 아니다. 본 발명에서 아릴기 또는 아릴렌기는 단일고리형, 고리집합체, 접합된 여러 고리계, 스파이로 화합물 등을 포함할 수 있다. 또한, 본 명세서에서 다른 설명이 없는 한 아릴기에는 플루오렌일기가 포함될 수 있고 아릴렌기에는 플루오렌일렌기가 포함될 수 있다.The terms "aryl group" and "arylene group" used in the present invention each have 6 to 60 carbon atoms, and are not limited thereto. In the present invention, 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. In addition, unless otherwise stated in the specification, a fluorenyl group may be included in the aryl group, and a fluorenylene group may be included in the arylene group.
본 발명에서 사용된 용어 "플루오렌일기"는 치환 또는 비치환된 플루오렌일기를, "플루오렌일렌기"는 치환 또는 비치환된 플루오렌일기를 의미하며, 본 발명에서 사용된 플루오렌일기 또는 플루오렌일렌기는 하기 구조에서 R과 R'이 서로 결합되어 형성된 스파이로 화합물을 포함하고, 이웃한 R"이 서로 결합하여 고리를 형성한 화합물도 포함한다. The term "fluorenyl group" used in the present invention refers to a substituted or unsubstituted fluorenyl group, and "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.
"치환된 플루오렌일기", "치환된 플루오렌일렌기"는 하기 구조에서 R, R', R" 중 적어도 하나가 수소 이외의 치환기인 것을 의미하며, 아래 화학식에서 R"은 1~8개일 수 있다. 본 명세서에서는 가수와 상관없이 플루오렌일기, 플루오렌일렌기, 플루오렌트리일기 등을 모두 플루오렌기라고 명명할 수도 있다."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. In the present specification, a fluorenyl group, a fluorenylene group, and a fluorenetriyl group may all be referred to as fluorene groups regardless of the valence.
Figure PCTKR2020010424-appb-I000002
Figure PCTKR2020010424-appb-I000002
본 발명에서 사용된 용어 "스파이로 화합물"은 '스파이로 연결'을 가지며, 스파이로 연결은 2개의 고리가 오로지 1개의 원자를 공유함으로써 이루어지는 연결을 의미한다. 이때, 두 고리에 공유된 원자를 '스파이로 원자'라 하며, 한 화합물에 들어 있는 스파이로 원자의 수에 따라 이들을 각각 '모노스파이로-', '다이스파이로-', '트라이스파이로-' 화합물이라 한다.The term "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.
본 발명에 사용된 용어 "헤테로고리기"는 "헤테로아릴기" 또는 "헤테로아릴렌기"와 같은 방향족 고리뿐만 아니라 비방향족 고리도 포함하며, 다른 설명이 없는 한 각각 하나 이상의 헤테로원자를 포함하는 탄소수 2 내지 60의 고리를 의미하나 여기에 제한되는 것은 아니다. 본 명세서에서 사용된 용어 "헤테로원자"는 다른 설명이 없는 한 N, O, S, P 또는 Si를 나타내며, 헤테로고리기는 헤테로원자를 포함하는 단일고리형, 고리집합체, 접합된 여러 고리계, 스파이로 화합물 등을 의미한다. 또한, 고리를 형성하는 탄소 대신 하기 화합물과 같이 SO2, P=O 등과 같은 헤테로원자단을 포함하는 화합물도 헤테로고리기에 포함될 수 있다.The term "heterocyclic group" as used in the present invention 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. The term "heteroatom" as used herein 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. In addition, a compound including a heteroatom group such as SO 2 , P=O, etc. instead of carbon forming a ring may be included in the heterocyclic group.
Figure PCTKR2020010424-appb-I000003
Figure PCTKR2020010424-appb-I000003
본 발명에 사용된 용어 "지방족고리기"는 방향족탄화수소를 제외한 고리형 탄화수소를의미하며, 단일고리형, 고리집합체, 접합된 여러 고리계, 스파이로 화합물 등을 포함하며, 다른 설명이 없는 한 탄소수 3 내지 60의 고리를의미하나 여기에 제한되는 것은 아니다. 예컨대, 방향족고리인 벤젠과 비방향족고리인 사이클로헥산이 융합된 경우에도 지방족고리에 해당한다.The term "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. For example, benzene as an aromatic ring and cyclohexane, a non-aromatic ring, are fused to an aliphatic ring.
본 명세서에서 각 기호 및 그 치환기의 예로 예시되는 아릴기, 아릴렌기, 헤테로고리기 등에 해당하는 '기 이름'은 '가수를 반영한 기의 이름'을 기재할 수도 있지만, '모체화합물 명칭'으로 기재할 수도 있다. 예컨대, 아릴기의 일종인 '페난트렌'의 경우, 1가의 '기'는 '페난트릴'로 2가의 기는 '페난트릴렌' 등과 같이 가수를 구분하여 기의 이름을 기재할 수도 있지만, 가수와 상관없이 모체 화합물 명칭인 '페난트렌'으로 기재할 수도 있다. 유사하게, 피리미딘의 경우에도, 가수와 상관없이 '피리미딘'으로 기재하거나, 1가인 경우에는 피리미딘일기, 2가의 경우에는 피리미딘일렌 등과 같이 해당 가수의 '기의 이름'으로 기재할 수도 있다. In the present specification, 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. For example, in the case of'phenanthrene', which is a kind of aryl group, 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'. Similarly, 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.
또한, 본 명세서에서는 화합물 명칭이나 치환기 명칭을 기재함에 있어 위치를 표시하는 숫자나 알파벳 등은 생략할 수도 있다. 예컨대, 피리도[4,3-d]피리미딘을 피리도피리미딘으로, 벤조퓨로[2,3-d]피리미딘을 벤조퓨로피리미딘으로, 9,9-다이메틸-9H-플루오렌을 다이메틸플루오렌 등과 같이 기재할 수 있다. 따라서, 벤조[g]퀴녹살린이나 벤조[f]퀴녹살린을 모두 벤조퀴녹살린이라고 기재할 수 있다.In addition, in the present specification, when describing the name of the compound or the name of the substituent, numbers or alphabets indicating positions may be omitted. For example, pyrido[4,3-d]pyrimidine to pyridopyrimidine, benzofuro[2,3-d]pyrimidine to benzofuropyrimidine, 9,9-dimethyl-9H-flu Orene can be described as dimethylfluorene or the like. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.
또한, 명시적인 설명이 없는 한,　본 발명에서 사용되는 화학식은 하기 화학식의 지수 정의에　의한 치환기 정의와 동일하게 적용된다.In addition, unless there is an explicit explanation, the formula used in the present invention is applied in the same way as the definition of the substituent group defined by the index definition of the following formula.
Figure PCTKR2020010424-appb-I000004
Figure PCTKR2020010424-appb-I000004
여기서, a가 0의 정수인 경우 치환기 R1은 부존재하는 것을 의미하는데, 즉 a가 0인 경우는 벤젠고리를 형성하는 탄소에 모두 수소가 결합된 것을 의미하며, 이때 탄소에 결합된 수소의 표시를 생략하고 화학식이나 화합물을 기재할 수 있다. 또한, a가 1의 정수인 경우 하나의 치환기 R1은 벤젠 고리를 형성하는 탄소 중 어느 하나의 탄소에 결합하며, a가 2 또는 3의 정수인 경우 예컨대 아래와 같이 결합할 수 있고, a가 4 내지 6의 정수인 경우에도 이와 유사한 방식으로 벤젠 고리의 탄소에 결합하며, a가 2 이상의 정수인 경우 R1은 서로 같거나 상이할 수 있다.Here, when a is an integer of 0, 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. In addition, when 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 In the case of an integer of, it is bonded to the carbon of the benzene ring in a similar manner, and when a is an integer of 2 or more, R 1 may be the same or different from each other.
Figure PCTKR2020010424-appb-I000005
Figure PCTKR2020010424-appb-I000005
또한, 본 명세서에서 다른 설명이 없는 한, 축합환을 표시할 때 '숫자-축합환'에서 숫자는 축합되는 고리의 개수를 나타낸다. 예컨대, 안트라센, 페난트렌, 벤조퀴나졸린 등과 같이 3개의 고리가 서로 축합한 형태는 3-축합환으로 표기할 수 있다.In addition, unless otherwise specified in the present specification, when indicating a condensed ring, a number in'number-condensed ring' indicates the number of condensed rings. For example, 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.
또한, 본 명세서에서 다른 설명이 없는 한, 5원자 고리, 6원자 고리 등과 같이 '숫자원자' 형식으로 고리를 표현한 경우, '숫자-원자'에서 숫자는 고리를 형성하는 원소의 개수를 나타낸다. 예컨대, 싸이오펜이나 퓨란 등은 5원자 고리에 해당할 수 있고, 벤젠이나 피리딘은 6원자 고리에 해당할 수 있다.In addition, unless otherwise specified in the specification, when a ring is 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. For example, thiophene or furan may correspond to a five-membered ring, and benzene or pyridine may correspond to a six-membered ring.
또한, 본 명세서에서 다른 설명이 없는 한, 이웃한 기끼리 서로 결합하여 형성한 고리는 C6~C60의 방향족고리기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 C3~C60의 지방족고리기;로 이루어진 군에서 선택될 수 있다. In addition, unless otherwise described in the specification, 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.
이때, 본 명세서에서 다른 설명이 없는 한, '이웃한 기끼리'라 함은, 하기 화학식을 예로 들어 설명하면, R1과 R2끼리, R2와 R3끼리, R3과 R4끼리, R5와 R6끼리 뿐만 아니라, 하나의 탄소를 공유하는 R7과 R8끼리도 포함되고, R1과 R7끼리, R1과 R8끼리 또는 R4와 R5끼리 등과 같이 바로 인접하지 않은 고리 구성 원소(탄소나 질소 등)에 결합된 치환기도 포함될 수 있다. 즉, 바로 인접한 탄소나 질소 등과 같은 고리 구성 원소에 치환기가 있을 경우에는 이들이 이웃한 기가 될 수 있지만, 바로 인접한 위치의 고리 구성 원소에 그 어떤 치환기도 결합되지 않은 경우에는 그 다음 고리 구성 원소에 결합된 치환기와 이웃한 기가 될 수 있고, 또한 동일 고리 구성 탄소에 결합된 치환기끼리도 이웃한 기라고 할 수 있다. At this time, unless otherwise described in the specification, 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 (such as carbon or nitrogen) may also be included. In other words, if there are 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.
하기 화학식에서 R7과 R8처럼 동일 탄소에 결합된 치환기가 서로 결합하여 고리를 형성할 경우에는 스파이로 모이어티가 포함된 화합물이 형성될 수 있다.In the following formula, when substituents bonded to the same carbon as R 7 and R 8 are bonded to each other to form a ring, a compound containing a spiro moiety may be formed.
Figure PCTKR2020010424-appb-I000006
,
Figure PCTKR2020010424-appb-I000007
Figure PCTKR2020010424-appb-I000006
,
Figure PCTKR2020010424-appb-I000007
또한, 본 명세서에서 '이웃한 기끼리 서로 결합하여 고리를 형성할 수 있다'라는 표현은 '이웃한 기끼리 서로 결합하여 선택적으로 고리를 형성한다'라는 것과 동일한 의미로 사용되며, 적어도 한 쌍의 이웃한 기끼리 서로 결합하여 고리를 형성하는 경우를 의미한다. In addition, in the present specification, 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.
이하, 본 발명의 화합물이 포함된 유기전기소자의 적층구조에 대하여 도 1 내지 도 3을 참조하여 설명한다.Hereinafter, a laminated structure of an organic electric device including the compound of the present invention will be described with reference to FIGS. 1 to 3.
각 도면의 구성요소들에 참조부호를 부가함에 있어서, 동일한 구성요소들에 대해서는 비록 다른 도면상에 표시되더라도 가능한 한 동일한 부호를 가지도록 하고 있음에 유의해야 한다. 또한, 본 발명을 설명함에 있어, 관련된 공지 구성 또는 기능에 대한 구체적인 설명이 본 발명의 요지를 흐릴 수 있다고 판단되는 경우에는 그 상세한 설명은 생략한다.In adding reference numerals to elements of each drawing, it should be noted that the same elements are assigned the same numerals as possible even if they are indicated on different drawings. In addition, in describing the present invention, if it is determined that a detailed description of a related known configuration or function may obscure the subject matter of the present invention, a detailed description thereof will be omitted.
본 발명의 구성 요소를 설명하는 데 있어서, 제1, 제2, A, B, (a), (b) 등의 용어를 사용할 수 있다. 이러한 용어는 그 구성 요소를 다른 구성 요소와 구별하기 위한 것일 뿐, 그 용어에 의해 해당 구성 요소의 본질이나 차례 또는 순서 등이 한정되지 않는다. 어떤 구성 요소가 다른 구성 요소에 "연결", "결합" 또는 "접속"된다고 기재된 경우, 그 구성 요소는 그 다른 구성 요소에 직접적으로 연결되거나 또는 접속될 수 있지만, 각 구성 요소 사이에 또 다른 구성 요소가 "연결", "결합" 또는 "접속"될 수도 있다고 이해되어야 할 것이다.In describing the constituent elements of the present invention, terms such as 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. When 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”.
또한, 층, 막, 영역, 판 등의 구성 요소가 다른 구성 요소 "위에" 또는 "상에" 있다고 하는 경우, 이는 다른 구성 요소 "바로 위에" 있는 경우뿐만 아니라 그 중간에 또 다른 구성 요소가 있는 경우도 포함할 수 있다고 이해되어야 할 것이다. 반대로, 어떤 구성 요소가 다른 부분 "바로 위에" 있다고 하는 경우에는 중간에 또 다른 부분이 없는 것을 뜻한다고 이해되어야 할 것이다.In addition, when a component such as a layer, film, region, or plate is said to be "on" or "on" another component, 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.
도 1 내지 도 3은 본 발명의 실시예에 따른 유기전기소자의 예시도이다.1 to 3 are exemplary views of an organic electric device according to an embodiment of the present invention.
도 1을 참조하면, 본 발명의 일 실시예에 따른 유기전기소자(100)는 기판(미도시) 상에 형성된 제1 전극(110)과, 제2 전극(170), 그리고 제1 전극(110)과 제2 전극(170) 사이에 형성된 유기물층을 포함한다.Referring to FIG. 1, an organic electric device 100 according to an embodiment of the present invention 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.
상기 제1 전극(110)은 애노드(양극)이고, 제2 전극(170)은 캐소드(음극)일 수 있으며, 인버트형의 경우에는 제1 전극이 캐소드이고 제2 전극이 애노드일 수 있다.The first electrode 110 may be an anode (anode), the second electrode 170 may be a cathode (cathode), and in the case of an inverted type, the first electrode may be a cathode and the second electrode may be an anode.
상기 유기물층은 정공주입층(120), 정공수송층(130), 발광층(140), 전자수송층(150) 및 전자주입층(160)을 포함할 수 있다. 구체적으로, 제1 전극(110) 상에 정공주입층(120), 정공수송층(130), 발광층(140), 전자수송층(150) 및 전자주입층(160)이 순차적으로 형성될 수 있다.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. Specifically, 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.
바람직하게는, 상기 제1 전극(110) 또는 제2 전극(170)의 양면 중에서 유기물층과 접하지 않는 일면에 광효율개선층(180)이 형성될 수 있으며, 광효율개선층(180)이 형성될 경우 유기전기소자의 광효율이 향상될 수 있다.Preferably, 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.
예를 들면, 제2 전극(170) 상에 광효율 개선층(180)이 형성될 수 있는데, 전면발광(top emission) 유기발광소자의 경우, 광효율 개선층(180)이 형성됨으로써 제2 전극(170)에서의 SPPs (surface plasmon polaritons)에 의한 광학 에너지 손실을 줄일 수 있고, 배면발광(bottom emission) 유기발광소자의 경우, 광효율 개선층(180)이 제2 전극(170)에 대한 완충 역할을 수행할 수 있다.For example, the light efficiency improvement layer 180 may be formed on the second electrode 170. In the case of a top emission organic light emitting device, the light efficiency improvement layer 180 is formed to form the second electrode 170. ), optical energy loss due to SPPs (surface plasmon polaritons) can be reduced, and in the case of a bottom emission organic light emitting device, the light efficiency improvement layer 180 performs a buffering role for the second electrode 170 can do.
정공수송층(130)과 발광층(140) 사이에 버퍼층(210)이나 발광보조층(220)이 더 형성될 수 있는데 이에 대해 도 2를 참조하여 설명한다.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.
도 2를 참조하면, 본 발명의 다른 실시예에 따른 유기전기소자(200)는 제1 전극(110) 상에 순차적으로 형성된 정공주입층(120), 정공수송층(130), 버퍼층(210), 발광보조층(220), 발광층(140), 전자수송층(150), 전자주입층(160), 제2 전극(170)을 포함할 수 있고, 제2 전극 상에 광효율개선층(180)이 형성될 수 있다.Referring to FIG. 2, an organic electric device 200 according to another embodiment of the present invention 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. Can be.
도 2에 도시되지는 않았으나, 발광층(140)과 전자수송층(150) 사이에 전자수송보조층이 더 형성될 수도 있다.Although not shown in FIG. 2, an electron transport auxiliary layer may be further formed between the light emitting layer 140 and the electron transport layer 150.
또한, 본 발명의 다른 실시예에 따르면 유기물층은 정공수송층, 발광층 및 전자수송층을 포함하는 스택이 복수개 형성된 형태일 수도 있다. 이에 대해 도 3을 참조하여 설명한다.In addition, according to another embodiment of the present invention, 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.
도 3을 참조하면, 본 발명의 또 다른 실시예에 따른 유기전기소자(300)는 제1 전극(110)과 제2 전극(170) 사이에 다층으로 이루어진 유기물층의 스택(ST1, ST2)이 두 세트 이상 형성될 수 있고 유기물층의 스택 사이에 전하 생성층(CGL)이 형성될 수도 있다.Referring to FIG. 3, in an organic electric device 300 according to another embodiment of the present invention, 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.
구체적으로, 본 발명에 일 실시예에 따른 유기전기소자는 제1 전극(110), 제1 스택(ST1), 전하 생성층(CGL: Charge Generation Layer), 제2 스택(ST2), 제2 전극(170) 및 광효율 개선층(180)을 포함할 수 있다. Specifically, the organic electric device according to the embodiment of the present invention 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.
제1 스택(ST1)은 제1 전극(110) 상에 형성된 유기물층으로, 이는 제1 정공주입층(320), 제1 정공수송층(330), 제1 발광층(340) 및 제1 전자수송층(350)을 포함할 수 있고, 제2 스택(ST2)은 제2 정공주입층(420), 제2 정공수송층(430), 제2 발광층(440) 및 제2 전자수송층(450)을 포함할 수 있다. 이와 같이 제1 스택과 제2 스택은 동일한 적층 구조를 갖는 유기물층일 수도 있지만 서로 다른 적층 구조의 유기물층일 수도 있다.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. ), and 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. . As described above, 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.
제1 스택(ST1)과 제2 스택(ST2) 사이에는 전하 생성층(CGL)이 형성될 수 있다. 전하 생성층(CGL)은 제1 전하 생성층(360)과 제2 전하 생성층(361)을 포함할 수 있다. 이러한 전하 생성층(CGL)은 제1 발광층(340)과 제2 발광층(440) 사이에 형성되어 각각의 발광층에서 발생하는 전류 효율을 증가시키고, 전하를 원활하게 분배하는 역할을 한다.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.
제1 발광층(340)에는 청색 호스트에 청색 형광 도펀트를 포함하는 발광 재료가 포함될 수 있고, 제2 발광층(440)에는 녹색 호스트에 그리니쉬 옐로우(greenish yellow) 도펀트와 적색 도펀트가 함께 도핑된 재료가 포함될 수 있으나, 본 발명의 실시예에 따른 제1 발광층(340) 및 제2 발광층(440)의 재료가 이에 한정되는 것은 아니다. 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.
도 3에서, n은 1~5의 정수일 수 있는데, n이 2인 경우, 제2 스택(ST2) 상에 전하 생성층(CGL)과 제3 스택이 추가적으로 더 적층될 수 있다.In FIG. 3, n may be an integer of 1-5. When n is 2, a charge generation layer CGL and a third stack may be additionally stacked on the second stack ST2.
도 3과 같이 다층의 스택 구조 방식에 의해 발광층이 복수개 형성될 경우, 각각의 발광층에서 발광된 광의 혼합 효과에 의해 백색 광이 발광되는 유기전기발광소자를 제조할 수 있을 뿐만 아니라 다양한 색상의 광을 발광하는 유기전기발광소자를 제조할 수도 있다.When a plurality of emission layers are formed by the multilayer stack structure method as shown in FIG. 3, it is possible to manufacture an organic electroluminescent device in which white light is emitted by the mixing effect of light emitted from each emission layer, as well as various colors of light. An organic electroluminescent device that emits light can also be manufactured.
본 발명의 화학식 1에 의해 표시되는 화합물은 정공주입층(120, 320, 420), 정공수송층(130, 330, 430), 버퍼층(210), 발광보조층(220), 전자수송층(150, 350, 450), 전자주입층(160), 발광층(140, 340, 440) 또는 광효율 개선층(180)의 재료로 사용될 수 있으나, 바람직하게는 발광층(140, 340, 440), 발광보조층(220) 및/또는 광효율 개선층(180)의 재료로 사용될 수 있다.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.
동일유사한 코어일지라도 어느 위치에 어느 치환기를 결합시키냐에 따라 밴드갭(band gap), 전기적 특성, 계면 특성 등이 달라질 수 있으므로, 코어의 선택 및 이에 결합된 서브(sub)-치환체의 조합에 대한 연구가 필요하며, 특히 각 유기물층 간의 에너지 준위 및 T1 값, 물질의 고유특성(이동도, 계면특성 등) 등이 최적의 조합을 이루었을 때 긴 수명과 높은 효율을 동시에 달성할 수 있다.Since the 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.
따라서, 본 발명에서는 화학식 1로 표시되는 화합물을 발광층(140, 340, 440), 발광보조층(220) 및/또는 광효율 개선층(180)의 재료로 사용함으로써, 각 유기물층 간의 에너지 레벨 및 T1 값, 물질의 고유특성(이동도, 계면특성 등) 등을 최적화하여 유기전기소자의 수명 및 효율을 동시에 향상시킬 수 있다.Therefore, in the present invention, by using 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 By optimizing the value and intrinsic properties of the material (mobility, interfacial properties, etc.), it is possible to simultaneously improve the life and efficiency of organic electric devices.
본 발명의 일 실시예에 따른 유기전기발광소자는 다양한 증착법(deposition)을 이용하여 제조될 수 있을 것이다. PVD나 CVD 등의 증착 방법을 사용하여 제조될 수 있는데, 예컨대, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극(110)을 형성하고, 그 위에 정공주입층(120), 정공수송층(130), 발광층(140), 전자수송층(150) 및 전자주입층(160)을 포함하는 유기물층을 형성한 후, 그 위에 음극(170)으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 또한, 정공수송층(130)과 발광층(140) 사이에 발광보조층(220)을, 발광층(140)과 전자수송층(150) 사이에 전자수송보조층(미도시)을 더 형성할 수도 있고 상술한 바와 같이 스택 구조로 형성할 수도 있다.The organic electroluminescent device according to an embodiment of the present invention 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. In addition, 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.
또한, 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 용액 공정 또는 솔벤트 프로세스(solvent process), 예컨대 스핀코팅 공정, 노즐 프린팅 공정, 잉크젯 프린팅 공정, 슬롯코팅 공정, 딥코팅 공정, 롤투롤 공정, 닥터 블레이딩 공정, 스크린 프린팅 공정, 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다. 본 발명에 따른 유기물층은 다양한 방법으로 형성될 수 있으므로, 그 형성방법에 의해 본 발명의 권리범위가 제한되는 것은 아니다.In addition, 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.
본 발명의 일 실시예에 따른 유기전기소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.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.
또한, 본 발명의 일 실시예에 따른 유기전기소자는 유기전기발광소자, 유기태양전지, 유기감광체, 유기트랜지스터, 단색 조명용 소자 및 퀀텀닷 디스플레이용 소자로 이루어진 군에서 선택될 수 있다.In addition, the organic electric device according to an embodiment of the present invention 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.
본 발명의 다른 실시예는 상술한 본 발명의 유기전기소자를 포함하는 디스플레이장치와, 이 디스플레이장치를 제어하는 제어부를 포함하는 전자장치를 포함할 수 있다. 이때, 전자장치는 현재 또는 장래의 유무선 통신단말일 수 있으며, 휴대폰 등의 이동 통신 단말기, PDA, 전자사전, PMP, 리모콘, 네비게이션, 게임기, 각종 TV, 각종 컴퓨터 등 모든 전자장치를 포함한다.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. At this time, 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.
이하, 본 발명의 일 측면에 따른 화합물에 대하여 설명한다.Hereinafter, a compound according to an aspect of the present invention will be described.
본 발명의 일 측면에 따른 화합물은 하기 화학식 1로 표시된다.A compound according to an aspect of the present invention is represented by the following formula (1).
<화학식 1><Formula 1>
Figure PCTKR2020010424-appb-I000008
Figure PCTKR2020010424-appb-I000008
상기 화학식 1에서, 각 기호는 아래와 같이 정의될 수 있다.In Formula 1, each symbol may be defined as follows.
R1 내지 R4는 서로 독립적으로 수소; 중수소; 할로겐; 시아노기; 니트로기; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; C1~C30의 알킬기; C2~C30의 알켄일기; C2~C30의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L-N(Ra)(Rb)로 이루어진 군에서 선택되고, 이웃한 기끼리 서로 결합하여 선택적으로 고리를 형성할 수 있다.R 1 to R 4 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 -LN (R a ) (R b ), and neighboring groups may be bonded to each other to selectively form a ring.
a 및 b는 각각 0~2의 정수, c 및 d는 각각 0~3의 정수이며, 이들 각각이 2 이상의 정수인 경우 R1 각각, R2 각각, R3 각각, R4 각각은 서로 같거나 상이하다.a and b are each an integer of 0 to 2, c and d are each an integer of 0 to 3, and when each is an integer of 2 or more, each of R 1, each of R 2, each of R 3, and each of R 4 is the same or different from each other Do.
이웃한 기끼리 서로 결합하여 형성한 고리는 C6~C60의 방향족고리기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 C3~C60의 지방족고리기;로 이루어진 군에서 선택될 수 있다. 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.
이웃한 기끼리 서로 결합하여 방향족고리를 형성할 경우, 바람직하게는 C6~C20의 방향족고리, 더욱 바람직하게는 C6~C14의 방향족고리, 예컨대 벤젠, 나프탈렌, 페난트렌 등을 형성하거나, 벤젠 모이어티가 포함된 고리를 형성할 수 있다.When adjacent groups are bonded to each other to form an 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.
R1 내지 R4 중 적어도 하나가 아릴기인 경우, 상기 아릴기는 바람직하게는 C6~C30의 아릴기, 더욱 바람직하게는 C6~C18의 아릴기, 예컨대 페닐, 나프틸, 바이페닐, 터페닐 등일 수 있다. When at least one of R 1 to R 4 is an aryl group, 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.
R1 내지 R4 중 적어도 하나가 헤테로고리기인 경우, 상기 헤테로고리는 바람직하게는 C2~C30의 헤테로고리기, 더욱 바람직하게는 C2~C18의 헤테로고리기, 예컨대 트리아진, 퀴나졸린, 벤조퀴나졸린, 다이벤조싸이오펜, 다이벤조퓨란, 나프토벤조퓨란, 나프토벤조싸이오펜, 카바졸, 페닐카바졸 등일 수 있다.When at least one of R 1 to R 4 is a heterocyclic group, the heterocycle is preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 18 heterocyclic group such as triazine, quina It may be sleepy, benzoquinazoline, dibenzothiophene, dibenzofuran, naphthobenzofuran, naphthobenzothiophene, carbazole, phenylcarbazole, and the like.
R1 내지 R4 중 적어도 하나가 알킬기인 경우, 상기 알킬기는 바람직하게는 C1~C10의 알킬기이며, 예컨대 메틸, t-부틸 등일 수 있다.When at least one of R 1 to R 4 is an alkyl group, the alkyl group is preferably a C 1 to C 10 alkyl group, such as methyl or t-butyl.
L1 및 L2는 서로 독립적으로 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; C3~C60의 지방족고리기; 및 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기로 이루어진 군에서 선택될 수 있다.L 1 and L 2 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.
L1 및 L2 중 적어도 하나가 아릴렌기인 경우, 상기 아릴렌기는 바람직하게는 C6~C30의 아릴렌기, 더욱 바람직하게는 C6~C18의 아릴렌기, 예컨대 페닐렌, 나프틸렌, 바이페닐렌, 터페닐 등일 수 있다. When at least one of L 1 and L 2 is an arylene group, the arylene group is preferably an arylene group of C 6 to C 30 , more preferably an arylene group of C 6 to C 18 such as phenylene, naphthylene, It may be biphenylene, terphenyl, and the like.
L1 및 L2 중 적어도 하나가 헤테로고리기인 경우, 상기 헤테로고리는 바람직하게는 C2~C30의 헤테로고리기, 더욱 바람직하게는 C2~C18의 헤테로고리기, 예컨대 피리딘, 피리미딘, 트리아진, 피라진, 카바졸, 페닐카바졸, 퀴나졸린, 벤조퀴나졸린, 퀴녹살린, 벤조퀴녹살린, 다이벤조퀴녹살린, 퀴놀린, 아이소퀴놀린, 벤조퀴놀린, 벤조싸이에노피리미딘, 벤조퓨로피리미딘, 다이벤조다이옥신, 페노싸이아진, 페녹사틴, 벤조이미다졸, 벤조싸이아졸, 인돌, 벤조옥사졸, 다이벤조싸이오펜, 다이벤조퓨란 등일 수 있다.When at least one of L 1 and L 2 is a heterocyclic group, the heterocycle is preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 18 heterocyclic group, such as pyridine, pyrimidine , Triazine, pyrazine, carbazole, phenylcarbazole, quinazoline, benzoquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, quinoline, isoquinoline, benzoquinoline, benzothienopyrimidine, benzofuro Pyrimidine, dibenzodioxin, phenothiazine, phenoxatin, benzoimidazole, benzothiazole, indole, benzoxazole, dibenzothiophene, dibenzofuran, and the like.
Ar1 및 Ar2는 서로 독립적으로 C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; 및 -L-N(Ra)(Rb)로 이루어진 군에서 선택될 수 있다.Ar 1 and Ar 2 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; C 3 ~ C 60 aliphatic ring group; And -LN(R a ) (R b ) It may be selected from the group consisting of.
Ar1 및 Ar2 중 적어도 하나가 아릴기인 경우, 상기 아릴기는 바람직하게는 C6~C30의 아릴기, 더욱 바람직하게는 C6~C18의 아릴기, 예컨대 페닐, 나프틸, 바이페닐, 터페닐, 페난트렌, 트리페닐렌, 파이렌, 크리센, 안트라센 등일 수 있다. When at least one of Ar 1 and Ar 2 is an aryl group, 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, phenanthrene, triphenylene, pyrene, chrysene, anthracene, and the like.
Ar1 및 Ar2 중 적어도 하나가 헤테로고리기인 경우, 상기 헤테로고리는 바람직하게는 C2~C30의 헤테로고리기, 더욱 바람직하게는 C2~C22의 헤테로고리기, 예컨대 피리딘, 피리미딘, 트리아진, 피라진, 카바졸, 페닐카바졸, 페닐벤조카바졸, 퀴나졸린, 벤조퀴나졸린, 퀴녹살린, 벤조퀴녹살린, 다이벤조퀴녹살린, 퀴놀린, 아이소퀴놀린, 벤조퀴놀린, 벤조싸이에노피리미딘, 벤조퓨로피리미딘, 다이벤조다이옥신, 페노싸이아진, 페녹사틴, 벤조이미다졸, 벤조싸이아졸, 인돌, 벤조옥사졸, 다이벤조싸이오펜, 다이벤조퓨란, 나프토벤조싸이오펜, 나프토벤조퓨란 등일 수 있다.When at least one of Ar 1 and Ar 2 is a heterocyclic group, the heterocycle is preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 22 heterocyclic group, such as pyridine, pyrimidine , Triazine, pyrazine, carbazole, phenylcarbazole, phenylbenzocarbazole, quinazoline, benzoquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, quinoline, isoquinoline, benzoquinoline, benzothienopyr Midine, benzofuropyrimidine, dibenzodioxin, phenothiazine, phenoxatin, benzoimidazole, benzothiazole, indole, benzoxazole, dibenzothiophene, dibenzofuran, naphthobenzothiophene, naphtho It may be benzofuran and the like.
Ar1 및 Ar2 중 적어도 하나가 플루오렌일기인 경우, 상기 플루오렌일기는 9,9-다이메틸-9H-플루오렌, 9,9-다이페닐-9H-플루오렌일기, 9,9'-스파이로바이플루오렌 등일 수 있다.When at least one of Ar 1 and Ar 2 is a fluorenyl group, the fluorenyl group is 9,9-dimethyl-9 H -fluorene, 9,9-diphenyl-9 H -fluorenyl group, 9,9 '- may be spyrobifluorene or the like.
Ar1 및 Ar2 중 적어도 하나가 지방족고리기인 경우, 상기 지방족고리기는 바람직하게는 C3~C30의 지방족고리기, 더욱 바람직하게는 C3~C10의 지방족고리기, 예컨대 사이클로헥산, 아다만틸 등일 수 있다.When at least one of Ar 1 and Ar 2 is an aliphatic ring group, the aliphatic ring group is preferably an aliphatic ring group of C 3 to C 30 , more preferably an aliphatic ring group of C 3 to C 10 such as cyclohexane, a It may be Damantil.
상기 L은 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택될 수 있다.L is 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.
L이 아릴렌기인 경우, 상기 아릴렌기는 바람직하게는 C6~C30의 아릴렌기, 더욱 바람직하게는 C6~C18의 아릴렌기, 예컨대 페닐렌, 나프틸렌, 바이페닐렌, 터페닐 등일 수 있다. When L is an arylene group, the arylene group is preferably a C 6 ~ C 30 arylene group, more preferably a C 6 ~ C 18 arylene group, such as phenylene, naphthylene, biphenylene, terphenyl, etc. I can.
상기 Ra 및 Rb는 서로 독립적으로 C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 C3~C60의 지방족고리기로 이루어진 군에서 선택될 수 있다.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.
Ra 및 Rb 중 적어도 하나가 아릴기인 경우, 상기 아릴기는 바람직하게는 C6~C30의 아릴기, 더욱 바람직하게는 C6~C18의 아릴기, 예컨대 페닐, 나프틸, 바이페닐, 터페닐 등일 수 있다. When at least one of R a and R b is an aryl group, 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.
Ra 및 Rb 중 적어도 하나가 헤테로고리기인 경우, 상기 헤테로고리는 바람직하게는 C2~C30의 헤테로고리기, 더욱 바람직하게는 C2~C12의 헤테로고리기, 예컨대 다이벤조싸이오펜, 다이벤조퓨란 등일 수 있다.When at least one of R a and R b is a heterocyclic group, the heterocycle is preferably a C 2 to C 30 heterocyclic group, more preferably a C 2 to C 12 heterocyclic group, such as dibenzothiophene , Dibenzofuran, and the like.
Ra 및 Rb 중 적어도 하나가 플루오렌일기인 경우, 상기 플루오렌일기는 9,9-다이메틸-9H-플루오렌, 9,9-다이페닐-9H-플루오렌일기, 9,9'-스파이로바이플루오렌 등일 수 있다.When at least one of R a and R b is a fluorenyl group, the fluorenyl group is 9,9-dimethyl-9 H -fluorene, 9,9-diphenyl-9 H -fluorenyl group, 9,9 '- may be spyrobifluorene or the like.
상기 R1~R4, L1, L2, Ar1, Ar2, 및 이웃한 기끼리 서로 결합하여 형성된 고리는 각각 중수소; 할로겐; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 실란기; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 포스핀옥사이드; 실록산기; 붕소기; 게르마늄기; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 지방족고리기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기로 이루어진 군에서 선택된 하나 이상의 치환기로 더 치환될 수 있다.The R 1 ~R 4 , L 1 , L 2 , Ar 1 , Ar 2 , and the rings formed by bonding of neighboring 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; 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 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 may be further substituted with one or more substituents selected from the group consisting of arylalkenyl group.
예시적으로, 상기 화학식 1은 하기 화학식 1-1 내지 1-6 중에서 하나로 표시될 수 있다.Illustratively, Formula 1 may be represented by one of Formulas 1-1 to 1-6 below.
<화학식 1-1> <화학식 1-2> <화학식 1-3><Formula 1-1> <Formula 1-2> <Formula 1-3>
Figure PCTKR2020010424-appb-I000009
Figure PCTKR2020010424-appb-I000009
<화학식 1-4> <화학식 1-5> <화학식 1-6><Formula 1-4> <Formula 1-5> <Formula 1-6>
Figure PCTKR2020010424-appb-I000010
Figure PCTKR2020010424-appb-I000010
상기 화학식 1-1 내지 화학식 1-6에서, R1~R4, a~d, L1, L2, Ar1, Ar2, L, Ra, Rb는 화학식 1에서 정의된 것과 같다.In Formulas 1-1 to 1-6, R 1 to R 4 , a to d, L 1 , L 2 , Ar 1 , Ar 2 , L, R a , R b are as defined in Formula 1.
또 다른 예시로, 상기 화학식 1은 하기 화학식 2-1 내지 2-6 중에서 하나로 표시될 수 있다.As another example, Formula 1 may be represented by one of Formulas 2-1 to 2-6 below.
<화학식 2-1> <화학식 2-2> <화학식 2-3><Formula 2-1> <Formula 2-2> <Formula 2-3>
Figure PCTKR2020010424-appb-I000011
Figure PCTKR2020010424-appb-I000011
<화학식 2-4> <화학식 2-5> <화학식 2-6><Formula 2-4> <Formula 2-5> <Formula 2-6>
Figure PCTKR2020010424-appb-I000012
Figure PCTKR2020010424-appb-I000012
상기 화학식 2-1 내지 2-6에서, R1~R4, a~d, L1, L2, Ar1, Ar2는 화학식 1에서 정의된 것과 같고, L6은 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택되며, X1~X6은 서로 독립적으로 C, C(R') 또는 N이고, X1~X6 중에서 적어도 하나는 N이고, X1~X6 중에서 하나는 C이다.In Formulas 2-1 to 2-6, R 1 to R 4 , a to d, L 1 , L 2 , Ar 1 , Ar 2 are the same as defined in Formula 1, and L 6 is 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 is selected from the group consisting of, X 1 ~ X 6 is independently C, C (R ') or N to each other, and at least one of X 1 ~ X 6 is N, X one of 1 ~ X 6 Is C.
상기 R'은 서로 독립적으로 수소; 중수소; 할로겐; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 실란기; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 지방족고리기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기로 이루어진 군에서 선택되며, 이웃한 기끼리 서로 결합하여 고리를 형성할 수 있다.R'is independently of each other 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; Cyano group; Nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; A C 6 -C 20 aryloxy 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 arylalkenyl group, neighboring groups may be bonded to each other to form a ring.
예시적으로, 상기 L1, L2 및 L은 서로 독립적으로 하기 화학식 b-1 내지 b-13으로 이루어진 그룹에서 선택될 수 있다.Exemplarily, the L 1 , L 2 and L may be independently selected from the group consisting of the following Formulas b-1 to b-13.
<화학식 b-1> <화학식 b-2> <화학식 b-3><Formula b-1> <Formula b-2> <Formula b-3>
Figure PCTKR2020010424-appb-I000013
Figure PCTKR2020010424-appb-I000013
<화학식 b-4> <화학식 b-5> <화학식 b-6><Formula b-4> <Formula b-5> <Formula b-6>
Figure PCTKR2020010424-appb-I000014
Figure PCTKR2020010424-appb-I000014
<화학식 b-7> <화학식 b-8> <화학식 b-9> <화학식 b-10><Formula b-7> <Formula b-8> <Formula b-9> <Formula b-10>
Figure PCTKR2020010424-appb-I000015
Figure PCTKR2020010424-appb-I000015
<화학식 b-11> <화학식 b-12> <화학식 b-13><Formula b-11> <Formula b-12> <Formula b-13>
Figure PCTKR2020010424-appb-I000016
Figure PCTKR2020010424-appb-I000016
상기 화학식 b-1 내지 화학식 b-13에서, Z는 O, S, N-(L'-Ar') 또는 C(R')(R")이고, Z49 내지 Z51은 서로 독립적으로 C, C(R') 또는 N이고, Z49 내지 Z51 중에서 적어도 하나는 N이고, Z49 내지 Z51 중에서 적어도 하나는 C이다.In Formulas b-1 to b-13, Z is O, S, N-(L'-Ar') or C(R')(R"), and Z 49 to Z 51 are each independently C, is C (R ') or N, Z 49 to Z 51, at least one of is N, Z 49 to Z 51 are C, at least one way.
R5 내지 R7, 상기 R' 및 R"은 서로 독립적으로 수소; 중수소; 할로겐; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 실란기; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 지방족고리기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기로 이루어진 군에서 선택되며, 이웃한 기끼리 서로 결합하여 고리를 형성할 수 있다.R 5 to R 7 , wherein 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; a cyano group; nitro group; a C 2 -C 20 alkenyl;; C 1 -C 20 alkylthio Sy of; C 1 -C 20 alkoxy group; C 6 -C 20 aryloxy; C 1 -C 20 alkyl C 2 -C 20 alkynyl group; C 6 -C 20 aryl group; fluorenyl group; C 2 -C 20 heterocycle containing at least one hetero atom selected from the group consisting of O, N, S, Si and P Group; C 3 -C 20 aliphatic ring group; C 7 -C 20 arylalkyl group; And C 8 -C 20 selected from the group consisting of arylalkenyl groups, neighboring groups can be bonded to each other to form a ring have.
a", c", d", e", g"는 각각 0~4의 정수, b"는 0~6의 정수, f"는 0~3의 정수, h"는 0~2의 정수, i"는 0~3의 정수이며, 이들 각각이 2 이상의 정수인 경우, R5 각각, R6 각각, R7 각각은 서로 같거나 상이하다.a", c", d", e", g" is an integer from 0 to 4, b" is an integer from 0 to 6, f" is an integer from 0 to 3, h" is an integer from 0 to 2, i "Is an integer of 0 to 3, and when each of them is an integer of 2 or more, each of R 5, each of R 6, and each of R 7 is the same as or different from each other.
상기 Ar'은 C6~C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C20의 헤테로고리기; C3~C20의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택될 수 있다.Ar' 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 of P; C 3 ~ C 20 aliphatic ring group; And it may be selected from the group consisting of a combination thereof.
상기 L'은 서로 독립적으로 단일결합; C6~C20의 아릴렌기; 플루오렌일렌기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C20의 헤테로고리기; 및 C3~C20의 지방족고리기로 이루어진 군에서 선택될 수 있다.L'is independently a single bond; C 6 ~ C 20 arylene group; Fluorenylene group; O, N, S, Si, and C 2 ~ C 20 heterocyclic group containing at least one heteroatom of P; And C 3 ~ C 20 It may be selected from the group consisting of an aliphatic ring group.
예시적으로, 상기 Ra 및 Rb 중에서 적어도 하나는 하기 화학식 B-1로 표시될 수 있다.Illustratively , at least one of R a and R b may be represented by the following Formula B-1.
<화학식 B-1><Formula B-1>
Figure PCTKR2020010424-appb-I000017
Figure PCTKR2020010424-appb-I000017
상기 화학식 B-1에서, A환 및 B환은 서로 독립적으로 C6~C20의 방향족고리기 또는 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C4~C20의 헤테로고리기이며, Z는 O, S, N-(L'-Ar') 또는 C(R')(R")이다.In Formula B-1, ring A and ring B are independently of each other C 6 ~ C 20 aromatic ring group or C 4 ~ C 20 hetero containing at least one heteroatom of O, N, S, Si and P And Z is O, S, N-(L'-Ar') or C(R')(R").
상기 R' 및 R"은 서로 독립적으로 수소; 중수소; 할로겐; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 실란기; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 지방족고리기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기로 이루어진 군에서 선택되며, 이웃한 기끼리 서로 결합하여 고리를 형성할 수 있다.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 cyano group; a nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; C 6 -C 20 aryloxy group; C 1 -C 20 alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkynyl group ; C 6 -C 20 aryl group; fluorenyl group; C 2 -C 20 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C It is selected from the group consisting of an aliphatic ring group of 20; C 7 -C 20 arylalkyl group; And C 8 -C 20 arylalkenyl group, and neighboring groups may be bonded to each other to form a ring.
상기 Ar'은 C6~C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C20의 헤테로고리기; C3~C20의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택될 수 있다.Ar' 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 of P; C 3 ~ C 20 aliphatic ring group; And it may be selected from the group consisting of a combination thereof.
상기 L'은 서로 독립적으로 단일결합; C6~C20의 아릴렌기; 플루오렌일렌기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C20의 헤테로고리기; 및 C3~C20의 지방족고리기로 이루어진 군에서 선택될 수 있다.L'is independently a single bond; C 6 ~ C 20 arylene group; Fluorenylene group; O, N, S, Si, and C 2 ~ C 20 heterocyclic group containing at least one heteroatom of P; And C 3 ~ C 20 It may be selected from the group consisting of an aliphatic ring group.
예시적으로, 상기 R1~R4, Ar1 및 Ar2 중에서 적어도 하나는 하기 화학식 A-1 내지 화학식 A-6으로 이루어진 군에서 선택될 수 있다.Exemplarily , at least one of R 1 to R 4 , Ar 1 and Ar 2 may be selected from the group consisting of the following Formulas A-1 to A-6.
<화학식 A-1> <화학식 A-2> <화학식 A-3><Formula A-1> <Formula A-2> <Formula A-3>
Figure PCTKR2020010424-appb-I000018
Figure PCTKR2020010424-appb-I000018
<화학식 A-4> <화학식 A-5> <화학식 A-6><Formula A-4> <Formula A-5> <Formula A-6>
Figure PCTKR2020010424-appb-I000019
Figure PCTKR2020010424-appb-I000019
상기 화학식 A-1 내지 화학식 A-6에서, L은 화학식 1에서 정의된 것과 같다.In Formulas A-1 to A-6, L is the same as defined in Formula 1.
화학식 A-1에서, X1-X6은 서로 독립적으로 C, C(R1) 또는 N이며, X1-X6 중에서 하나는 연결기 L과 결합하는 C이다. 바람직하게는 X1-X6 중에서 적어도 하나는 N이다.In Formula A-1, X 1 -X 6 are each independently C, C(R 1 ) or N, and one of X 1 -X 6 is C bonded to a linking group L. Preferably, at least one of X 1 -X 6 is N.
화학식 A-2에서, X1-X4는 서로 독립적으로 C, C(R1) 또는 N이며, X1-X4 중에서 하나는 연결기 L과 결합하는 C이며, Y1-Y4는 서로 독립적으로 C(R1) 또는 N이다. 바람직하게는 X1-X4와 Y1~Y4 중에서 적어도 하나는 N이다.In Formula A-2, X 1 -X 4 are each independently C, C(R 1 ) or N , one of X 1 -X 4 is C bonded to a linking group L, and Y 1 -Y 4 are independent of each other By C(R 1 ) or N. Preferably, at least one of X 1 -X 4 and Y 1 to Y 4 is N.
화학식 A-3에서, X1-X6은 서로 독립적으로 C, C(R1) 또는 N이며, X1-X6 중에서 하나는 연결기 L과 결합하는 C이며, Y1-Y4는 서로 독립적으로 C(R1) 또는 N이다. 바람직하게는 X1-X6과 Y1~Y4 중에서 적어도 하나는 N이다.In Formula A-3, X 1 -X 6 are independently of each other C, C(R 1 ) or N , one of X 1 -X 6 is C bonded to a linking group L, and Y 1 -Y 4 are independent of each other By C(R 1 ) or N. Preferably, at least one of X 1 -X 6 and Y 1 to Y 4 is N.
화학식 A-4에서, X1-X4는 서로 독립적으로 C, C(R1) 또는 N이며, X1-X4 중에서 하나는 연결기 L과 결합하는 C이며, Y1-Y8은 서로 독립적으로 C(R1) 또는 N이다. 바람직하게는 X1-X4와 Y1-Y8 중에서 적어도 하나는 N이다.In Formula A-4, X 1 -X 4 are each independently C, C(R 1 ) or N , one of X 1 -X 4 is C bonded to a linking group L, and Y 1 -Y 8 are independent of each other By C(R 1 ) or N. Preferably, at least one of X 1 -X 4 and Y 1 -Y 8 is N.
화학식 A-5에서, X1-X4는 서로 독립적으로 C, C(R1) 또는 N이며, Y1-Y4는 서로 독립적으로 C(R1) 또는 N이고, V 및 W는 서로 독립적으로 O, S, N, N-(L'-Ar'), C(R') 또는 C(R')(R")이고, e와 f는 각각 0 또는 1이며, e와 f 중에서 적어도 하나는 1이고, X1-X4 중에서 하나가 연결기 L과 결합되는 C이거나, V와 W 중에서 하나가 연결기 L과 결합되는 N 또는 C(R')이다. 바람직하게는, X1-X4, 중에서 적어도 하나가 N이거나/이고 V, W 중에서 적어도 하나가 N 또는 N-(L'-Ar')이다.In Formula A-5, X 1 -X 4 are each independently C, C(R 1 ) or N, Y 1 -Y 4 are each independently C(R 1 ) or N, and V and W are independently of each other As O, S, N, N-(L'-Ar'), C(R') or C(R')(R"), e and f are each 0 or 1, at least one of e and f Is 1, and one of X 1 -X 4 is C bonded to the linking group L, or one of V and W is N or C(R′) bonded to the linking group L. Preferably, X 1 -X 4 , At least one of them is N or/and at least one of V and W is N or N-(L'-Ar').
화학식 A-6에서, X1-X4, X6은 서로 독립적으로 C, C(R1) 또는 N이며, Y1은 O, S, N, N-(L'-Ar'), C(R') 또는 C(R')(R")이며, Y2는 N이다. 바람직하게는 X1-X4, X6 중에서 하나가 N이거나/이고 Y1이 N 또는 N-(L'-Ar')일 수 있다.In Formula A-6, X 1 -X 4 , X 6 are each independently C, C(R 1 ) or N, and Y 1 is O, S, N, N-(L'-Ar'), C( R') or C(R')(R"), and Y 2 is N. Preferably, one of X 1 -X 4 and X 6 is N or/and Y 1 is N or N-(L'- Ar').
상기 R1, R' 및 R"은 서로 독립적으로 수소; 중수소; 할로겐; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 실란기; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 지방족고리기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기로 이루어진 군에서 선택되며, 이웃한 기끼리 서로 결합하여 고리를 형성할 수 있다.The R 1 , 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 cyano group; a nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; C 6 -C 20 aryloxy group; C 1 -C 20 alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 Alkynyl group; C 6 -C 20 aryl group; fluorenyl group; C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C It is selected from the group consisting of 3 -C 20 aliphatic ring group; C 7 -C 20 arylalkyl group; And C 8 -C 20 arylalkenyl group, and neighboring groups may be bonded to each other to form a ring.
상기 Ar'은 C6~C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C20의 헤테로고리기; C3~C20의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택될 수 있다.Ar' 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 of P; C 3 ~ C 20 aliphatic ring group; And it may be selected from the group consisting of a combination thereof.
상기 L'은 서로 독립적으로 단일결합; C6~C20의 아릴렌기; 플루오렌일렌기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C20의 헤테로고리기; 및 C3~C20의 지방족고리기로 이루어진 군에서 선택될 수 있다.L'is independently a single bond; C 6 ~ C 20 arylene group; Fluorenylene group; O, N, S, Si, and C 2 ~ C 20 heterocyclic group containing at least one heteroatom of P; And C 3 ~ C 20 It may be selected from the group consisting of an aliphatic ring group.
구체적으로, 상기 화학식 1로 표시되는 화합물은 하기 화합물 중에서 하나일 수 있으나, 이에 한정되는 것은 아니다.Specifically, the compound represented by Formula 1 may be one of the following compounds, but is not limited thereto.
Figure PCTKR2020010424-appb-I000020
Figure PCTKR2020010424-appb-I000020
Figure PCTKR2020010424-appb-I000021
Figure PCTKR2020010424-appb-I000021
Figure PCTKR2020010424-appb-I000022
Figure PCTKR2020010424-appb-I000022
Figure PCTKR2020010424-appb-I000023
Figure PCTKR2020010424-appb-I000023
Figure PCTKR2020010424-appb-I000024
.
Figure PCTKR2020010424-appb-I000024
.
본 발명의 다른 측면에서, 본 발명은 양극, 음극, 및 상기 양극과 음극 사이에 형성된 유기물층을 포함하는 유기전기소자를 제공하고, 이때 유기물층은 상기 화학식 1로 표시되는 화합물을 포함한다.In another aspect of the present invention, 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.
본 발명의 또 다른 측면에서, 본 발명은 양극, 음극, 상기 양극과 음극 사이에 형성된 유기물층 및 광효율 개선층을 포함하는 유기전기소자를 제공한다. 이때, 광효율 개선층은 상기 양극 또는 음극의 양면 중에서 상기 유기물층과 접하지 않는 일면에 형성되며, 상기 유기물층 또는 광효율 개선층은 상기 화학식 1로 표시되는 화합물을 포함한다.In yet another aspect of the present invention, 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. In this case, 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.
상기 유기물층은 정공주입층, 정공수송층, 발광보조층, 발광층, 전자수송보조층, 전자수송층 및 전자주입층 중 적어도 하나의 층을 포함하고, 바람직하게는 상기 화합물은 발광층 및/또는 발광보조층에 포함될 수 있다.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.
상기 유기물층은 상기 양극 상에 순차적으로 형성된 정공수송층, 발광층 및 전자수송층을 포함하는 스택을 둘 이상 포함할 수 있으며, 상기 둘 이상의 스택 사이에 형성된 전하생성층을 더 포함할 수 있다.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.
본 발명의 또 다른 측면에서, 본 발명은 상기 화학식 1로 표시되는 유기전기소자를 포함하는 디스플레이장치와, 상기 디스플레이장치를 구동하는 제어부를 포함하는 전자장치를 제공한다.In yet another aspect of the present invention, 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.
이하에서는 본 발명에 따른 화학식 1로 표시되는 화합물의 합성예 및 유기전기소자의 제조예에 관하여 실시예를 들어 구체적으로 설명하지만, 본 발명이 하기의 실시예로 한정되는 것은 아니다.Hereinafter, examples for synthesizing the compound represented by Chemical Formula 1 according to the present invention and an example for preparing an organic electric device will be described in detail, but the present invention is not limited to the following examples.
합성예Synthesis example
본 발명에 따른 화학식 1로 표시되는 화합물(Final product)은 하기 반응식 1과 같이 Sub 1과 Sub 2를 반응시켜 합성될 수 있으나, 이에 한정되는 것은 아니다.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.
<반응식 1><Reaction Scheme 1>
Figure PCTKR2020010424-appb-I000025
Figure PCTKR2020010424-appb-I000025
I. Sub 1의 I. of Sub 1 합성예Synthesis example
상기 반응식 1의 Sub 1은 하기 반응식 2의 반응경로에 의해 합성될 수 있으나, 이에 한정되는 것은 아니다.Sub 1 of Scheme 1 may be synthesized by the reaction route of Scheme 2 below, but is not limited thereto.
<반응식 2><Reaction Scheme 2>
Figure PCTKR2020010424-appb-I000026
Figure PCTKR2020010424-appb-I000026
Sub 1-IV-1의 합성예시Synthesis example of Sub 1-IV-1
Figure PCTKR2020010424-appb-I000027
Figure PCTKR2020010424-appb-I000027
(1) Sub 1-I-1 합성(1) Sub 1-I-1 synthesis
1,8-dibromonaphthalene (50 g, 174.8 mmol)을 둥근바닥플라스크에 넣고 THF 350 mL로 녹인 후에, (2-nitrophenyl)boronic acid (29.2 g, 174.8 mmol), Pd(PPh3)4 (6.1 g, 5.3 mmol), NaOH (21 g, 524.5 mmol), 물 175 mL를 첨가하고 80℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 40.7 g (수율: 71 %)을 얻었다.1,8-dibromonaphthalene (50 g, 174.8 mmol) was added to a round bottom flask and dissolved in 350 mL of THF, followed by (2-nitrophenyl)boronic acid (29.2 g, 174.8 mmol), Pd(PPh 3 ) 4 (6.1 g, 5.3 mmol), NaOH (21 g, 524.5 mmol), and 175 mL of water were added, followed by stirring at 80°C. When the reaction was completed, the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 40.7 g (yield: 71%) of the product.
(2) Sub 1-II-1 합성(2) Sub 1-II-1 synthesis
Figure PCTKR2020010424-appb-I000028
Figure PCTKR2020010424-appb-I000028
Sub 1-I-1 (40.7 g, 124 mmol), (2-nitrophenyl)boronic acid (20.7 g, 124 mmol)를 반응물로 사용하여 상기 Sub 1-I-1의 합성법과 같은 방법으로 진행시켜서 생성물 35.4 g (수율 : 77 %)을 얻었다.Sub 1-I-1 (40.7 g, 124 mmol), (2-nitrophenyl) boronic acid (20.7 g, 124 mmol) was used as a reactant and proceeded in the same manner as the synthesis method of Sub 1-I-1, and the product 35.4 g (yield: 77%) was obtained.
(3) Sub 1-III-1 합성(3) Sub 1-III-1 synthesis
Figure PCTKR2020010424-appb-I000029
Figure PCTKR2020010424-appb-I000029
Sub 1-II-1 (35.4 g, 95.6 mmol)을 둥근바닥플라스크에 넣고 DMF 200 mL로 녹인 후에, PPh3 (75.2 g, 286.8 mmol)을 첨가하고 165℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 24.9 g (수율: 85 %)을 얻었다.Add Sub 1-II-1 (35.4 g, 95.6 mmol) to a round bottom flask and dissolve with 200 mL of DMF, then PPh 3 (75.2 g, 286.8 mmol) was added and stirred at 165°C. When the reaction was completed, the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 24.9 g (yield: 85%) of the product.
(4) Sub 1-IV-1 합성(4) Sub 1-IV-1 synthesis
Figure PCTKR2020010424-appb-I000030
Figure PCTKR2020010424-appb-I000030
Sub 1-III-1 (24.9 g, 81.3 mmol), NaCl (8.1 g, 203.2 mmol), AlCl3(54.2 g, 406.4 mmol)을 벤젠에 용해시킨 후 용융물을 가수 분해했다. 반응이 완료되면 이 벤젠용액을 NaHCO3 수용액과 물로 세척하고 MgSO4로 건조하고 농축한 후 소량의 고온의 p-xylene으로 녹였다. 이후, 실리카겔 칼럼으로 분리 후, methylcyclohexane으로 재결정하여 생성물 9.2 g (수율: 37 %)을 얻었다.Sub 1-III-1 (24.9 g, 81.3 mmol), NaCl (8.1 g, 203.2 mmol), and AlCl 3 (54.2 g, 406.4 mmol) were dissolved in benzene, and the melt was hydrolyzed. When the reaction was complete, the benzene solution was washed with NaHCO 3 aqueous solution and water, dried over MgSO 4 , concentrated, and dissolved with a small amount of high-temperature p-xylene. Then, after separation by silica gel column, the product was recrystallized with methylcyclohexane to obtain 9.2 g (yield: 37%).
Sub 1-1의 합성예시Synthesis example of Sub 1-1
Figure PCTKR2020010424-appb-I000031
Figure PCTKR2020010424-appb-I000031
Sub 1-IV-1 (9.3 g, 30.6 mmol)을 둥근바닥플라스크에 넣고 toluene (100 mL)으로 녹인 후, iodobenzene (6.2 g, 30.6 mmol), Pd2(dba)3 (0.8 g, 0.9 mmol), P(t-Bu)3 (0.4 g, 1.8 mmol), NaOt-Bu(8.8 g, 91.7 mmol)을 첨가하고 100℃에서 교반하였다. 반응 완료 후 CH2Cl2와 물을 사용해 추출한 유기층을 MgSO4로 건조하고 증발기로 농축하였다. 이후, 농축물을 실리카겔 컬럼으로 분리 후 재결정하여 생성물 7.7 g (수율 : 66 %)을 얻었다.Sub 1-IV-1 (9.3 g, 30.6 mmol) was added to a round bottom flask and dissolved with toluene (100 mL), followed by iodobenzene (6.2 g, 30.6 mmol), Pd 2 (dba) 3 (0.8 g, 0.9 mmol) , P( t- Bu) 3 (0.4 g, 1.8 mmol), NaO t- Bu (8.8 g, 91.7 mmol) was added and stirred at 100°C. After completion of the reaction, the organic layer extracted with CH 2 Cl 2 and water was dried over MgSO 4 and concentrated with an evaporator. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 7.7 g (yield: 66%) of the product.
Sub 1-9의 합성예시Synthesis example of Sub 1-9
Figure PCTKR2020010424-appb-I000032
Figure PCTKR2020010424-appb-I000032
Sub 1-IV-2 (7.8 g, 16.5 mmol)과 chlorobenzene (1.9 g, 16.5 mmol)을 사용하여 상기 Sub 1-1의 합성법과 같은 방법으로 진행시켜서 생성물 6.2 g (수율: 68 %)를 얻었다.Sub 1-IV-2 (7.8 g, 16.5 mmol) and chlorobenzene (1.9 g, 16.5 mmol) were used in the same manner as for the synthesis of Sub 1-1 to obtain 6.2 g (yield: 68%) of the product.
Sub 1-30의 합성예시Synthesis example of Sub 1-30
Figure PCTKR2020010424-appb-I000033
Figure PCTKR2020010424-appb-I000033
Sub 1-IV-1 (7.8 g, 25.6 mmol)과 2-chlorobenzonaphthothiophene (6.9 g, 25.6 mmol)을 사용하여 상기 Sub 1-1의 합성법과 같은 방법으로 진행시켜서 생성물 7.8 g (수율: 57 %)를 얻었다.Using Sub 1-IV-1 (7.8 g, 25.6 mmol) and 2-chlorobenzonaphthothiophene (6.9 g, 25.6 mmol), proceed in the same manner as the synthesis method of Sub 1-1 to obtain 7.8 g of the product (yield: 57%). Got it.
Sub 1-33의 합성예시Synthesis example of Sub 1-33
Figure PCTKR2020010424-appb-I000034
Figure PCTKR2020010424-appb-I000034
Sub 1-IV-1 (14.5 g, 47.6 mmol)과 2-chloro-4,6-diphenyl-1,3,5-triazine (3.4 g, 47.6 mmol)을 사용하여 상기 Sub 1-1의 합성법과 같은 방법으로 진행시켜서 생성물 15.8 g (수율: 62 %)를 얻었다.Same as the synthesis method of Sub 1-1 using Sub 1-IV-1 (14.5 g, 47.6 mmol) and 2-chloro-4,6-diphenyl-1,3,5-triazine (3.4 g, 47.6 mmol) Proceeding to the method to give the product 15.8 g (yield: 62%).
Sub 1에 속하는 화합물은 아래와 같은 화합물일 수 있으나, 이에 한정되는 것은 아니며, 표 1은 하기 화합물의 FD-MS(Field Desorption-Mass Spectrometry) 값을 나타낸 것이다.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.
Figure PCTKR2020010424-appb-I000035
Figure PCTKR2020010424-appb-I000035
[표 1][Table 1]
Figure PCTKR2020010424-appb-I000036
Figure PCTKR2020010424-appb-I000036
II. Sub 2의 예시II. Sub 2 example
상기 반응식 1의 Sub 2에 속하는 화합물은 아래와 같은 화합물일 수 있으나, 이에 한정되는 것은 아니며, 표 2는 하기 화합물의 FD-MS(Field Desorption-Mass Spectrometry) 값을 나타낸 것이다.The compound belonging to Sub 2 of Scheme 1 may be a compound as follows, but is not limited thereto, and Table 2 shows the FD-MS (Field Desorption-Mass Spectrometry) values of the following compounds.
Figure PCTKR2020010424-appb-I000037
Figure PCTKR2020010424-appb-I000037
Figure PCTKR2020010424-appb-I000038
Figure PCTKR2020010424-appb-I000038
[표 2][Table 2]
Figure PCTKR2020010424-appb-I000039
Figure PCTKR2020010424-appb-I000039
Figure PCTKR2020010424-appb-I000040
Figure PCTKR2020010424-appb-I000040
III. 최종 화합물의 III. Of the final compound 합성예Synthesis example
P-2 합성예시Synthesis example of P-2
Figure PCTKR2020010424-appb-I000041
Figure PCTKR2020010424-appb-I000041
Sub 1-1 (9.3 g, 30.6 mmol)을 toluene으로 녹인 후, Sub 2-2 (5 g, 26.5 mmol), Pd2(dba)3 (0.8 g, 0.9 mmol), P(t-Bu)3 (0.4 g, 1.8 mmol), NaOt-Bu(8.8 g, 91.7 mmol)을 첨가하고 100℃에서 교반하였다. 반응 완료 후 CH2Cl2와 물을 사용해 추출한 유기층을 MgSO4로 건조하고 증발기로 농축하였다. 이후, 농축물을 실리카겔 컬럼으로 분리 후 재결정하여 생성물 12.3 g (수율 : 87 %)을 얻었다.After dissolving Sub 1-1 (9.3 g, 30.6 mmol) with toluene, Sub 2-2 (5 g, 26.5 mmol), Pd 2 (dba) 3 (0.8 g, 0.9 mmol), P( t -Bu) 3 (0.4 g, 1.8 mmol), NaO t -Bu (8.8 g, 91.7 mmol) was added and stirred at 100°C. After completion of the reaction, the organic layer extracted with CH 2 Cl 2 and water was dried over MgSO 4 and concentrated with an evaporator. Thereafter, the concentrate was separated by a silica gel column and recrystallized to obtain 12.3 g (yield: 87%) of the product.
P-7 합성예시Synthesis example of P-7
Figure PCTKR2020010424-appb-I000042
Figure PCTKR2020010424-appb-I000042
Sub 1-1 (12.5 g, 32.9 mmol)과 Sub 2-7 (7.2 g, 32.9 mmol)을 사용하여 상기 P-2의 합성법과 같이 진행시켜서 생성물 13.5 g (수율 : 73 %)을 얻었다.Using Sub 1-1 (12.5 g, 32.9 mmol) and Sub 2-7 (7.2 g, 32.9 mmol), the product 13.5 g (yield: 73%) was obtained by proceeding according to the synthesis method of P-2.
P-102 합성예시Synthesis example of P-102
Figure PCTKR2020010424-appb-I000043
Figure PCTKR2020010424-appb-I000043
Sub 1-9 (11.2 g, 20.5 mmol)과 Sub 2-73 (5.4 g, 20.5 mmol)을 사용하여 상기 P-2의 합성법과 같이 진행시켜서 생성물 11.9 g (수율 : 75 %)을 얻었다.Using Sub 1-9 (11.2 g, 20.5 mmol) and Sub 2-73 (5.4 g, 20.5 mmol), the product 11.9 g (yield: 75%) was obtained by proceeding according to the synthesis method of P-2.
P-121 합성예시Synthesis example of P-121
Figure PCTKR2020010424-appb-I000044
Figure PCTKR2020010424-appb-I000044
Sub 1-26 (11.8 g, 25.8 mmol)과 Sub 2-59 (6.5 g, 25.8 mmol)을 사용하여 상기 P-2의 합성법과 같이 진행시켜서 생성물 13.9 g (수율 : 80 %)을 얻었다.Sub 1-26 (11.8 g, 25.8 mmol) and Sub 2-59 (6.5 g, 25.8 mmol) were used in the same manner as in the synthesis of P-2 to obtain 13.9 g (yield: 80%) of the product.
P-144 합성예시Synthesis example of P-144
Figure PCTKR2020010424-appb-I000045
Figure PCTKR2020010424-appb-I000045
Sub 1-1 (10.8 g, 28.4 mmol)과 Sub 2-94 (6.5 g, 28.4 mmol)을 사용하여 상기 P-2의 합성법과 같이 진행시켜서 생성물 12.4 g (수율 : 76 %)을 얻었다.Using Sub 1-1 (10.8 g, 28.4 mmol) and Sub 2-94 (6.5 g, 28.4 mmol), the product 12.4 g (yield: 76%) was obtained by proceeding according to the synthesis method of P-2.
상기와 같은 합성예에 따라 제조된 본 발명의 화합물 P-1 내지 P-157의 FD-MS 값은 하기 표 3과 같다.The FD-MS values of the compounds P-1 to P-157 of the present invention prepared according to the synthesis example as described above are shown in Table 3 below.
[표 3][Table 3]
Figure PCTKR2020010424-appb-I000046
Figure PCTKR2020010424-appb-I000046
Figure PCTKR2020010424-appb-I000047
Figure PCTKR2020010424-appb-I000047
Figure PCTKR2020010424-appb-I000048
Figure PCTKR2020010424-appb-I000048
유기전기소자의 제조평가Manufacturing evaluation of organic electric devices
[[ 실시예Example 1] One] 적색유기발광소자Red organic light emitting device (인광호스트)(Phosphorescent host)
유리 기판에 형성된 ITO층(양극) 상에 N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine (이하 "2-TNATA"로 약기함)막을 진공증착하여 60 nm 두께의 정공주입층을 형성한 후, N,N'-Bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (이하"NPB"로 약기함) 막을 60 nm 두께로 진공증착하여 정공수송층을 형성하였다. On the ITO layer (anode) formed on the glass substrate, 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.
이후, 상기 정공수송층 상에 본 발명의 화합물 P-11을 호스트 물질로, bis-(1-phenylisoquinolyl)iridium(Ⅲ)acetylacetonate (이하, "(piq)2Ir(acac)"로 약기함)를 도펀트 물질로 사용하되 이들 중량비가 94:6이 되도록 도펀트를 도핑하여 30nm 두께의 발광층을 증착하였다. Thereafter, the compound P-11 of the present invention as a host material on the hole transport layer, bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter, abbreviated as "(piq) 2 Ir(acac)") as a dopant Although used as a material, a light emitting layer having a thickness of 30 nm was deposited by doping with a dopant so that the weight ratio was 94:6.
다음으로, 상기 발광층 상에 (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (이하 "BAlq"로 약기함)을 10 nm 두께로 진공증착하여 정공저지층을 형성하고, 상기 정공저지층 상에 트리스(8-퀴놀리놀)알루미늄(이하 Alq3로 약칭함)을 40 nm 두께로 성막하여 전자수송층을 형성하였다. Next, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as "BAlq") was vacuum-deposited to a thickness of 10 nm on the emission layer to form a hole blocking layer. And tris(8-quinolinol)aluminum (hereinafter abbreviated as Alq 3 ) was deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer.
이후, 전자수송층 상에 LiF를 0.2 nm 두께로 증착하여 전자주입층을 형성하고, 상기 전자주입층 상에 Al을 150 nm의 두께로 증착하여 음극을 형성하였다.Thereafter, LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and Al was deposited on the electron injection layer to a thickness of 150 nm to form a cathode.
[[ 실시예Example 2] 내지 [ 2] to [ 실시예Example 17] 17]
호스트 물질로 본 발명의 화합물 P-11 대신 하기 표 4에 기재된 본 발명의 화합물을 사용한 점을 제외하고는 상기 실시예 1과 동일한 방법으로 유기전기발광소자를 제작하였다.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 4 was used instead of the compound of the present invention P-11 as a host material.
[[ 비교예Comparative example 1] 및 [ 1] and [ 비교예Comparative example 2] 2]
호스트 물질로 본 발명의 화합물 P-11 대신 하기 비교화합물 1 또는 비교화합물 2를 사용하는 점을 제외하고는 상기 실시예 1과 동일한 방법으로 유기전기발광소자를 제작하였다.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 instead of Compound P-11 of the present invention as a host material.
<비교화합물 1> <비교화합물 2> <Comparative compound 1> <Comparative compound 2>
Figure PCTKR2020010424-appb-I000049
Figure PCTKR2020010424-appb-I000049
상기와 같이 제조된 본 발명의 실시예 1 내지 17, 비교예 1 및 2의 유기전기발광소자에 순바이어스 직류전압을 가하여 포토리서치(photoresearch)사의 PR-650으로 전기발광(EL) 특성을 측정하고, 2500cd/m2 기준 휘도에서 맥사이언스사에서 제조된 수명 측정 장비로 T95 수명을 측정하였다. 측정 결과는 하기 표 4와 같다.By applying a forward bias DC voltage to the organic electroluminescent devices of Examples 1 to 17 and Comparative Examples 1 and 2 of the present invention prepared as described above, electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch, and , T95 life was measured with a life measurement equipment manufactured by McScience at a reference luminance of 2500 cd/m 2. The measurement results are shown in Table 4 below.
[표 4][Table 4]
Figure PCTKR2020010424-appb-I000050
Figure PCTKR2020010424-appb-I000050
상기 표 4의 결과로부터 알 수 있듯이, 본 발명의 화합물을 발광층의 호스트 재료로 사용할 경우, 비교화합물 1 또는 비교화합물 2를 사용한 경우에 비해 소자의 구동전압이 낮아지고 효율과 수명이 현저히 개선되었다.As can be seen from the results of Table 4, when the compound of the present invention is used as a host material for the light emitting layer, the driving voltage of the device is lowered and efficiency and lifespan are significantly improved compared to the case of using Comparative Compound 1 or Comparative Compound 2.
본 발명의 화합물은 카바졸 모이어티 2개가 가운데 7원자 고리에 축합된 코어라는 점에서 비교화합물 1 및 2와 구조적으로 차이가 있는데, 이러한 차이점으로 인해 본 발명의 화합물은 정공 특성이 향상되고 밴드갭이 좁아져 구동전압 및 효율이 향상된 것으로 보이며, 또한 본 발명의 화합물은 비교화합물과 비교하여 평면성이 증가하고 높은 Tg 값을 갖게 되어 수명 또한 현저하게 향상된 것으로 보인다.The compounds of the present invention are structurally different from Comparative Compounds 1 and 2 in that the two carbazole moieties are a core condensed on the middle 7-membered ring. Due to these differences, the compounds of the present invention have improved hole properties and band gap. This narrowing seems to improve driving voltage and efficiency. In addition, the compound of the present invention has increased planarity and a high Tg value compared to the comparative compound, and thus the lifespan is also remarkably improved.
[[ 실시예Example 18] 내지 [ 18] to [ 실시예Example 26] 26] 녹색유기전기발광소자Green organic electroluminescent device (( 발광보조층Light-emitting auxiliary layer ))
유리 기판에 형성된 ITO층(양극) 위에 2-TNATA 막을 진공증착하여 60 nm 두께로 정공주입층을 형성한 후, NPB를 진공증하여 60 nm 두께의 정공수송층을 형성하였다. 이어서, 상기 정공수송층 상에 본 발명의 화합물 1-75를 20nm의 두께로 진공증착하여 발광보조층을 형성하였다.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.
이어서, 상기 정공수송층 상에 하기 표 5에 기재된 본 발명의 화합물을 20nm의 두께로 진공증착하여 발광보조층을 형성한 후, 상기 발광보조층 상에 호스트로 4,4'-N,N'-dicarbazole-biphenyl (이하, CBP로 약기함)을, 도펀트로 tris(2-phenylpyridine)-iridium (이하, "Ir(ppy)3라 함)을 사용하되 중량비가 93:7가 되도록 도펀트를 도핑하여 30 nm두께의 발광층을 형성하였다.Subsequently, after vacuum deposition of the compound of the present invention shown in Table 5 to a thickness of 20 nm on the hole transport layer to form a light emission auxiliary layer, 4,4'-N,N'- as a host on the light emission auxiliary layer Dicarbazole-biphenyl (hereinafter, abbreviated as CBP), tris(2-phenylpyridine)-iridium (hereinafter referred to as "Ir(ppy) 3 ) as a dopant, but doped with a dopant so that the weight ratio is 93:7. An nm-thick emission layer was formed.
다음으로, 상기 발광층 상에 BAlq를 10 nm 두께로 진공증착하여 정공저지층을 형성하고, 상기 정공저지층 상에 Alq3를 40 nm 두께로 성막하여 전자수송층을 형성하였다. Next, BAlq was vacuum deposited on the emission layer to a thickness of 10 nm to form a hole blocking layer, and Alq 3 was deposited on the hole blocking layer to a thickness of 40 nm to form an electron transport layer.
이후, 전자수송층 상에 LiF를 0.2 nm 두께로 증착하여 전자주입층을 형성하고, 상기 전자주입층 상에 Al을 150 nm의 두께로 증착하여 음극을 형성하였다.Thereafter, LiF was deposited to a thickness of 0.2 nm on the electron transport layer to form an electron injection layer, and Al was deposited on the electron injection layer to a thickness of 150 nm to form a cathode.
[[ 비교예Comparative example 3] 3]
발광보조층을 형성하지 않은 것을 제외하고는 상기 실시예 18과 동일한 방법으로 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 18, except that the light emission auxiliary layer was not formed.
[[ 비교예Comparative example 4] 내지 [ 4] to [ 비교예Comparative example 6] 6]
발광보조층 재료로 본 발명의 화합물 대신 하기 비교화합물 3 내지 비교화합물 5 중 하나를 사용한 점을 제외하고는 상기 실시예 18과 동일한 방법으로 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 18, except that one of the following Comparative Compounds 3 to 5 was used instead of the compound of the present invention as the light emitting auxiliary layer material.
<비교화합물 3> <비교화합물 4> <비교화합물 5><Comparative compound 3> <Comparative compound 4> <Comparative compound 5>
Figure PCTKR2020010424-appb-I000051
Figure PCTKR2020010424-appb-I000051
상기 실시예 18 내지 26, 비교예 3 내지 6에 의해 제조된 유기전기발광소자에 순바이어스 직류전압을 가하여 포토리서치(photoresearch)사의 PR-650으로 전기발광(EL) 특성을 측정하고, 5000cd/m2 기준 휘도에서 맥사이언스사에서 제조된 수명 측정 장비로 T95 수명을 측정하였다. 그 측정 결과는 하기 표 5와 같다.By applying a forward bias DC voltage to the organic electroluminescent devices prepared according to Examples 18 to 26 and Comparative Examples 3 to 6, electroluminescence (EL) characteristics were measured with a PR-650 of photoresearch, and 5000 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 5 below.
[표 5][Table 5]
Figure PCTKR2020010424-appb-I000052
Figure PCTKR2020010424-appb-I000052
상기 표 5의 결과로부터, 본 발명의 화합물은 비교화합물 1 내지 5와 유사하지만 N을 포함하는 피롤리딘 모이어티가 코어에 도입됨으로써 소자의 성능향상에 주요 인자로 작용하는 것을 알 수 있다.From the results of Table 5, it can be seen that the compounds of the present invention are similar to Comparative Compounds 1 to 5, but the introduction of a pyrrolidine moiety containing N into the core acts as a major factor in improving the performance of the device.
발광보조층이 형성되지 않은 유기전기소자(비교예 3)보다는 비교화합물 3 내지 비교화합물 5를 사용하여 발광보조층을 형성한 경우(비교예 4~6) 소자의 구동전압이 낮아지고 효율 및 수명이 향상되었다.When the light emission auxiliary layer is formed using Comparative Compound 3 to Comparative Compound 5 rather than an organic electric device in which the light emission auxiliary layer is not formed (Comparative Examples 4 to 6), the driving voltage of the device is lowered and the efficiency and lifespan This was improved.
그리고, 비교화합물 3 내지 5 중에서 하나를 사용한 경우에 비해 본 발명의 화합물을 발광보조층 재료로 사용시 구동전압이 낮아지고 효율 및 수명이 현저히 향상되었으며, 특히 수명이 현저히 향상되었다. 이는 피롤리딘 모이어티가 더 도입된 본 발명의 화합물은 비교화합물 3 내지 비교화합물 5보다 정공 수송능력이 향상되고, 밴드갭이 좁기 때문에 발광 효율 및 구동전압이 개선된 것으로 보인다.And, compared to the case of using one of Comparative Compounds 3 to 5, when the compound of the present invention is used as a light emitting auxiliary layer material, the driving voltage is lowered, the efficiency and lifespan are significantly improved, and in particular, the lifespan is significantly improved. This is because the compound of the present invention to which the pyrrolidine moiety is further introduced has improved hole transport capacity and narrower band gap than Comparative Compounds 3 to 5, and thus luminous efficiency and driving voltage were improved.
이러한 결과는 기본골격이 유사한 화합물일지라도, 본 발명과 같이 피롤리딘 고리가 더 도입됨에 따라서 Hole 특성, 광효율 특성, 에너지 레벨 등과 같은 화합물의 물성이 달라지게 되고, 이로 인해 예측 곤란한 소자결과가 도출될 수 있음을 시사하고 있다.These results show that even if the basic skeleton is a similar compound, as the pyrrolidine ring is further introduced as in the present invention, the physical properties of the compound such as hole characteristics, light efficiency characteristics, energy level, etc. are changed, resulting in device results that are difficult to predict. Suggests that you can.
표 4 및 표 5의 설명은 본 발명을 예시적으로 설명한 것에 불과한 것으로, 본 발명에 속하는 기술분야에서 통상의 지식을 가지는 자라면 본 발명의 본질적인 특성에서 벗어나지 않는 범위에서 발광층에 다른 화합물을 포함하여 성능을 개선시키는 방법 등 다양한 변형이 가능할 것이다. The descriptions in Tables 4 and 5 are merely illustrative of the present invention, and those of ordinary skill in the art to include other compounds in the light emitting layer within the range not departing from the essential characteristics of the present invention. Various variations are possible, including ways to improve performance.
이상의 설명은 본 발명을 예시적으로 설명한 것에 불과한 것으로, 본 발명에 속하는 기술분야에서 통상의 지식을 가지는 자라면 본 발명의 본질적인 특성에서 벗어나지 않는 범위에서 다양한 변형이 가능할 것이다. 따라서, 본 명세서에 개시된 실시예들은 본 발명을 한정하기 위한 것이 아니라 설명하기 위한 것이고, 이러한 실시예에 의하여 본 발명의 사상과 범위가 한정되는 것은 아니다. 본 발명의 보호범위는 아래의 청구범위에 의하여 해석되어야 하며, 그와 동등한 범위 내의 모든 기술은 본 발명의 권리범위에 포함하는 것으로 해석되어야 할 것이다.The above description is only illustrative of the present invention, and those of ordinary skill in the art to which the present invention pertains will be able to make various modifications without departing from the essential characteristics of the present invention. Accordingly, the embodiments disclosed in the present specification are not intended to limit the present invention, but to explain the present invention, and the spirit and scope of the present invention are not limited by these embodiments. The scope of protection of the present invention should be interpreted by the following claims, and all technologies within the scope equivalent thereto should be interpreted as being included in the scope of the present invention.
CROSS-REFERENCE TO RELATED APPLICATIONCROSS-REFERENCE TO RELATED APPLICATION
본 특허출원은 2019년 08월 20일 한국에 출원한 특허출원번호 제10-2019-0101507호에 대해 미국 특허법 119조 내지 121조, 365조 (35 U.S.C §119조 내지 §121조, §365조)에 따라 우선권을 주장하며, 그 모든 내용은 참고문헌으로 본 특허출원에 병합된다. 아울러, 본 특허출원은 미국 이외에 국가에 대해서도 위와 동일한 이유로 우선권을 주장하면 그 모든 내용은 참고문헌으로 본 특허출원에 병합된다.This patent application is for patent application No. 10-2019-0101507 filed in Korea on August 20, 2019, in the U.S. Patent Law Articles 119 to 121, 365 (35 USC §119 to §121, §365) ), and all the contents are incorporated into this patent application by reference. In addition, if this patent application claims priority for countries other than the United States for the same reason as above, all the contents are incorporated into this patent application as references.

Claims (15)

  1. 하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1):
    <화학식 1><Formula 1>
    Figure PCTKR2020010424-appb-I000053
    Figure PCTKR2020010424-appb-I000053
    상기 화학식 1에서,In Formula 1,
    R1 내지 R4는 서로 독립적으로 수소; 중수소; 할로겐; 시아노기; 니트로기; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; C1~C30의 알킬기; C2~C30의 알켄일기; C2~C30의 알킨일기; C1~C30의 알콕실기; C6~C30의 아릴옥시기; 및 -L-N(Ra)(Rb)로 이루어진 군에서 선택되고, 이웃한 기끼리 서로 결합하여 고리를 형성할 수 있으며,R 1 to R 4 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 -LN (R a ) (R b ), and neighboring groups can be bonded to each other to form a ring,
    a 및 b는 각각 0~2의 정수, c 및 d는 각각 0~3의 정수이며, 이들 각각이 2 이상의 정수인 경우 R1 각각, R2 각각, R3 각각, R4 각각은 서로 같거나 상이하며,a and b are each an integer of 0 to 2, c and d are each an integer of 0 to 3, and when each is an integer of 2 or more, each of R 1, each of R 2, each of R 3, and each of R 4 are the same or different And
    L1 및 L2는 서로 독립적으로 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; C3~C60의 지방족고리기; 및 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기로 이루어진 군에서 선택되며, L 1 and L 2 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 is selected from the group consisting of a heterocyclic group of C 2 ~ C 60 containing at least one heteroatom,
    Ar1 및 Ar2는 서로 독립적으로 C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; 및 -L-N(Ra)(Rb)로 이루어진 군에서 선택되며,Ar 1 and Ar 2 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; C 3 ~ C 60 aliphatic ring group; And -LN (R a ) (R b ) is selected from the group consisting of,
    상기 L은 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택되며,L is 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 is selected from the group consisting of a combination thereof,
    상기 Ra 및 Rb는 서로 독립적으로 C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 C3~C60의 지방족고리기로 이루어진 군에서 선택되며,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 is selected from the group consisting of an aliphatic ring group,
    상기 R1~R4, L1, L2, Ar1, Ar2, 및 이웃한 기끼리 서로 결합하여 형성된 고리는 각각 중수소; 할로겐; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 실란기; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 포스핀옥사이드; 실록산기; 붕소기; 게르마늄기; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 지방족고리기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기로 이루어진 군에서 선택된 하나 이상의 치환기로 더 치환될 수 있다.The R 1 ~R 4 , L 1 , L 2 , Ar 1 , Ar 2 , and the rings formed by bonding of adjacent groups to each other are deuterium; 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 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 may be further substituted with one or more substituents selected from the group consisting of arylalkenyl group.
  2. 제 1항에 있어서The method of claim 1
    상기 화학식 1은 하기 화학식 1-1 내지 1-6 중에서 하나로 표시되는 것을 특징으로 하는 화합물:Formula 1 is a compound characterized in that represented by one of the following formulas 1-1 to 1-6:
    <화학식 1-1> <화학식 1-2> <화학식 1-3><Formula 1-1> <Formula 1-2> <Formula 1-3>
    Figure PCTKR2020010424-appb-I000054
    Figure PCTKR2020010424-appb-I000054
    <화학식 1-4> <화학식 1-5> <화학식 1-6><Formula 1-4> <Formula 1-5> <Formula 1-6>
    Figure PCTKR2020010424-appb-I000055
    Figure PCTKR2020010424-appb-I000055
    상기 화학식 1-1 내지 화학식 1-6에서, R1~R4, a~d, L1, L2, Ar1, Ar2, L, Ra, Rb는 제1항에서 정의된 것과 같다.In Formulas 1-1 to 1-6, R 1 to R 4 , a to d, L 1 , L 2 , Ar 1 , Ar 2 , L, R a , R b are as defined in claim 1 .
  3. 제 1항에 있어서The method of claim 1
    상기 화학식 1은 하기 화학식 2-1 내지 2-6 중에서 하나로 표시되는 것을 특징으로 하는 화합물:Formula 1 is a compound characterized in that represented by one of the following formulas 2-1 to 2-6:
    <화학식 2-1> <화학식 2-2> <화학식 2-3><Formula 2-1> <Formula 2-2> <Formula 2-3>
    Figure PCTKR2020010424-appb-I000056
    Figure PCTKR2020010424-appb-I000056
    <화학식 2-4> <화학식 2-5> <화학식 2-6><Formula 2-4> <Formula 2-5> <Formula 2-6>
    Figure PCTKR2020010424-appb-I000057
    Figure PCTKR2020010424-appb-I000057
    상기 화학식 2-1 내지 2-6에서, R1~R4, a~d, L1, L2, Ar1, Ar2는 제1항에서 정의된 것과 같고, In Formulas 2-1 to 2-6, R 1 to R 4 , a to d, L 1 , L 2 , Ar 1 , Ar 2 are the same as defined in claim 1,
    L6은 단일결합; C6~C60의 아릴렌기; 플루오렌일렌기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택되며,L 6 is 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 is selected from the group consisting of a combination thereof,
    X1~X6은 서로 독립적으로 C, C(R') 또는 N이고, X1~X6 중에서 적어도 하나는 N이며,X 1 to X 6 are each independently C, C(R') or N, and at least one of X 1 to X 6 is N,
    상기 R'은 서로 독립적으로 수소; 중수소; 할로겐; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 실란기; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 지방족고리기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기로 이루어진 군에서 선택되며, 이웃한 기끼리 서로 결합하여 고리를 형성할 수 있다.R'is independently of each other 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; Cyano group; Nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; A C 6 -C 20 aryloxy 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 arylalkenyl group, neighboring groups may be bonded to each other to form a ring.
  4. 제 1항에 있어서,The method of claim 1,
    상기 L1, L2, L은 하기 화학식 b-1 내지 b-13로 이루어진 그룹에서 선택되는 것을 특징으로 하는 화합물:Wherein L 1 , L 2 , L is a compound, characterized in that selected from the group consisting of the following formulas b-1 to b-13:
    <화학식 b-1> <화학식 b-2> <화학식 b-3><Formula b-1> <Formula b-2> <Formula b-3>
    Figure PCTKR2020010424-appb-I000058
    Figure PCTKR2020010424-appb-I000058
    <화학식 b-4> <화학식 b-5> <화학식 b-6><Formula b-4> <Formula b-5> <Formula b-6>
    Figure PCTKR2020010424-appb-I000059
    Figure PCTKR2020010424-appb-I000059
    <화학식 b-7> <화학식 b-8> <화학식 b-9> <화학식 b-10><Formula b-7> <Formula b-8> <Formula b-9> <Formula b-10>
    Figure PCTKR2020010424-appb-I000060
    Figure PCTKR2020010424-appb-I000060
    <화학식 b-11> <화학식 b-12> <화학식 b-13><Formula b-11> <Formula b-12> <Formula b-13>
    Figure PCTKR2020010424-appb-I000061
    Figure PCTKR2020010424-appb-I000061
    상기 화학식 b-1 내지 화학식 b-13에서,In Formulas b-1 to b-13,
    Z는 O, S, N-(L'-Ar') 또는 C(R')(R")이고,Z is O, S, N-(L'-Ar') or C(R')(R"),
    Z49 내지 Z51은 서로 독립적으로 C, C(R') 또는 N이고, Z49 내지 Z51 중에서 적어도 하나는 N이며, Z 49 to Z 51 are each independently C, C(R') or N, and at least one of Z 49 to Z 51 is N,
    R5 내지 R7, 상기 R' 및 R"은 서로 독립적으로 수소; 중수소; 할로겐; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 실란기; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 지방족고리기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기로 이루어진 군에서 선택되며, 이웃한 기끼리 서로 결합하여 고리를 형성할 수 있으며, R'과 R"끼리 서로 결합하여 고리를 형성할 수 있고,R 5 to R 7 , wherein 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; a cyano group; nitro group; a C 2 -C 20 alkenyl;; C 1 -C 20 alkylthio Sy of; C 1 -C 20 alkoxy group; C 6 -C 20 aryloxy; C 1 -C 20 alkyl C 2 -C 20 alkynyl group; C 6 -C 20 aryl group; fluorenyl group; C 2 -C 20 heterocycle containing at least one hetero atom selected from the group consisting of O, N, S, Si and P Group; C 3 -C 20 aliphatic ring group; C 7 -C 20 arylalkyl group; And C 8 -C 20 selected from the group consisting of arylalkenyl groups, neighboring groups can be bonded to each other to form a ring And R'and R" can be bonded to each other to form a ring,
    a", c", d", e", g"는 각각 0~4의 정수, b"는 0~6의 정수, f"는 0~3의 정수, h"는 0~2의 정수, i"는 0~3의 정수이며, 이들 각각이 2 이상의 정수인 경우, R5 각각, R6 각각, R7 각각은 서로 같거나 상이하며,a", c", d", e", g" is an integer from 0 to 4, b" is an integer from 0 to 6, f" is an integer from 0 to 3, h" is an integer from 0 to 2, i "Is an integer of 0 to 3, and when each of them is an integer of 2 or more, each of R 5, each of R 6, and each of R 7 is the same or different from each other,
    상기 Ar'은 C6~C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C20의 헤테로고리기; C3~C20의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택되며,Ar' 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 of P; C 3 ~ C 20 aliphatic ring group; And it is selected from the group consisting of a combination thereof,
    상기 L'은 서로 독립적으로 단일결합; C6~C20의 아릴렌기; 플루오렌일렌기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C20의 헤테로고리기; 및 C3~C20의 지방족고리기로 이루어진 군에서 선택된다.L'is independently a single bond; C 6 ~ C 20 arylene group; Fluorenylene group; O, N, S, Si, and C 2 ~ C 20 heterocyclic group containing at least one heteroatom of P; And C 3 ~ C 20 is selected from the group consisting of an aliphatic ring group.
  5. 제 1항에 있어서The method of claim 1
    Ra 및 Rb 중에서 적어도 하나는 하기 화학식 B-1로 표시되는 것을 특징으로 하는 화합물:At least one of R a and R b is a compound characterized in that it is represented by the following formula B-1:
    <화학식 B-1><Formula B-1>
    Figure PCTKR2020010424-appb-I000062
    Figure PCTKR2020010424-appb-I000062
    상기 화학식 B-1에서,In Formula B-1,
    A환 및 B환은 서로 독립적으로 C6~C20의 방향족고리기 또는 O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C4~C20의 헤테로고리기이며,Ring A and Ring B are independently of each other an aromatic ring group of C 6 ~ C 20 or a heterocyclic group of C 4 ~ C 20 containing at least one heteroatom of O, N, S, Si and P,
    Z는 O, S, N-(L'-Ar') 또는 C(R')(R")이고,Z is O, S, N-(L'-Ar') or C(R')(R"),
    상기 R' 및 R"은 서로 독립적으로 수소; 중수소; 할로겐; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 실란기; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 지방족고리기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기로 이루어진 군에서 선택되며, R'과 R"끼리 서로 결합하여 고리를 형성할 수 있으며,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 cyano group; a nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; C 6 -C 20 aryloxy group; C 1 -C 20 alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkynyl group ; C 6 -C 20 aryl group; fluorenyl group; C 2 -C 20 heterocyclic group including at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C 20 aliphatic ring group; C 7 -C 20 arylalkyl group; And C 8 -C 20 is selected from the group consisting of arylalkenyl group, R'and R" may be bonded to each other to form a ring,
    상기 Ar'은 C6~C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C20의 헤테로고리기; C3~C20의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택되며,Ar' 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 of P; C 3 ~ C 20 aliphatic ring group; And it is selected from the group consisting of a combination thereof,
    상기 L'은 서로 독립적으로 단일결합; C6~C20의 아릴렌기; 플루오렌일렌기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C20의 헤테로고리기; 및 C3~C20의 지방족고리기로 이루어진 군에서 선택된다.L'is independently a single bond; C 6 ~ C 20 arylene group; Fluorenylene group; O, N, S, Si, and C 2 ~ C 20 heterocyclic group containing at least one heteroatom of P; And C 3 ~ C 20 is selected from the group consisting of an aliphatic ring group.
  6. 제 1항에 있어서,The method of claim 1,
    R1~R4, Ar1 및 Ar2 중에서 적어도 하나는 하기 화학식 A-1 내지 화학식 A-6으로 이루어진 군에서 선택되는 것을 특징으로 하는 화합물:At least one of R 1 to R 4 , Ar 1 and Ar 2 is selected from the group consisting of the following Formulas A-1 to A-6:
    <화학식 A-1> <화학식 A-2> <화학식 A-3><Formula A-1> <Formula A-2> <Formula A-3>
    Figure PCTKR2020010424-appb-I000063
    Figure PCTKR2020010424-appb-I000063
    <화학식 A-4> <화학식 A-5> <화학식 A-6><Formula A-4> <Formula A-5> <Formula A-6>
    Figure PCTKR2020010424-appb-I000064
    Figure PCTKR2020010424-appb-I000064
    상기 화학식 A-1 내지 화학식 A-6에서, L은 제1항에서 정의된 것과 같고,In Formulas A-1 to A-6, L is the same as defined in claim 1,
    X1~X6은 서로 독립적으로 C, C(R1) 또는 N이며, X 1 ~ X 6 are each independently C, C (R 1 ) or N,
    Y1~Y8은 서로 독립적으로 C(R1) 또는 N이며, Y 1 to Y 8 are independently of each other C(R 1 ) or N,
    상기 화학식 A-1에서, X1~X6 중에서 적어도 하나는 N이며,In Formula A-1, at least one of X 1 to X 6 is N,
    상기 화학식 A-2에서, X1~X4, Y1~Y4 중에서 적어도 하나는 N이며,In Formula A-2, at least one of X 1 to X 4 and Y 1 to Y 4 is N,
    상기 화학식 A-3에서, X1~X6 중에서 적어도 하나는 N이며,In Formula A-3, at least one of X 1 to X 6 is N,
    상기 화학식 A-4에서, X1~X4, Y1~Y8 중에서 적어도 하나는 N이며,In Formula A-4, at least one of X 1 to X 4 and Y 1 to Y 8 is N,
    상기 화학식 A-5 및 화학식 A-6에서, X1~X4 중에서 적어도 하나는 N이며,In Formulas A-5 and A-6, at least one of X 1 to X 4 is N,
    V 및 W는 O, S, N-(L'-Ar') 또는 C(R')(R")이고, e와 f는 각각 0 또는 1이며, e와 f 중에서 적어도 하나는 1이며,V and W are O, S, N-(L'-Ar') or C(R')(R"), e and f are each 0 or 1, at least one of e and f is 1,
    Y1는 O, S, N, N-(L'-Ar'), C(R') 또는 C(R')(R")이며, Y2는 N이고,Y 1 is O, S, N, N-(L'-Ar'), C(R') or C(R')(R"), Y 2 is N,
    상기 R1, R' 및 R"은 서로 독립적으로 수소; 중수소; 할로겐; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 실란기; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C20의 헤테로고리기; C3-C20의 지방족고리기; C7-C20의 아릴알킬기; 및 C8-C20의 아릴알켄일기로 이루어진 군에서 선택되며, 이웃한 기끼리 서로 결합하여 고리를 형성할 수 있으며, R'과 R"끼리 서로 결합하여 고리를 형성할 수 있고,The R 1 , 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 cyano group; a nitro group; C 1 -C 20 alkylthio group; C 1 -C 20 alkoxy group; C 6 -C 20 aryloxy group; C 1 -C 20 alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 Alkynyl group; C 6 -C 20 aryl group; fluorenyl group; C 2 -C 20 heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C 20 aliphatic ring group; C 7 -C 20 arylalkyl group; And C 8 -C 20 selected from the group consisting of arylalkenyl group, neighboring groups may be bonded to each other to form a ring, R 'And R'can combine with each other to form a ring
    상기 Ar'은 C6~C20의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C20의 헤테로고리기; C3~C20의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택되며,Ar' 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 of P; C 3 ~ C 20 aliphatic ring group; And it is selected from the group consisting of a combination thereof,
    상기 L'은 서로 독립적으로 단일결합; C6~C20의 아릴렌기; 플루오렌일렌기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C20의 헤테로고리기; 및 C3~C20의 지방족고리기로 이루어진 군에서 선택된다.L'is independently a single bond; C 6 ~ C 20 arylene group; Fluorenylene group; O, N, S, Si, and C 2 ~ C 20 heterocyclic group containing at least one heteroatom of P; And C 3 ~ C 20 is selected from the group consisting of an aliphatic ring group.
  7. 제 1항에 있어서,The method of claim 1,
    상기 화학식 1로 표시되는 화합물은 하기 화합물 중에서 하나인 것을 특징으로 하는 화합물:The compound represented by Formula 1 is a compound characterized in that one of the following compounds:
    Figure PCTKR2020010424-appb-I000065
    Figure PCTKR2020010424-appb-I000065
    Figure PCTKR2020010424-appb-I000066
    Figure PCTKR2020010424-appb-I000066
    Figure PCTKR2020010424-appb-I000067
    Figure PCTKR2020010424-appb-I000067
    Figure PCTKR2020010424-appb-I000068
    Figure PCTKR2020010424-appb-I000068
    Figure PCTKR2020010424-appb-I000069
    .
    Figure PCTKR2020010424-appb-I000069
    .
  8. 양극, 음극, 및 상기 양극과 음극 사이에 형성된 유기물층을 포함하는 유기전기소자에 있어서,In an organic electric device comprising an anode, a cathode, and an organic material layer formed between the anode and the cathode,
    상기 유기물층은 제1항의 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기전기소자.The organic electroluminescent device, characterized in that the organic material layer comprises a compound represented by the formula (1) of claim 1.
  9. 제 8항에 있어서,The method of claim 8,
    상기 양극의 양면 또는 상기 음극의 양면 중에서 상기 유기물층과 접하지 않는 일면에 형성된 광효율 개선층을 더 포함하는 것을 특징으로 하는 유기전기소자.An organic electric device, further comprising a light efficiency improving layer formed on one surface of the anode or both surfaces of the cathode that is not in contact with the organic material layer.
  10. 제 8항에 있어서,The method of claim 8,
    상기 유기물층은 정공주입층, 정공 수송층, 발광보조층, 발광층, 전자수송보조층, 전자수송층 및 전자주입층 중 적어도 하나를 포함하는 것을 특징으로 하는 유기전기소자.The organic material layer comprises 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.
  11. 제 10항에 있어서,The method of claim 10,
    상기 화합물은 상기 발광층 및 발광보조층 중에서 적어도 하나에 포함되는 것을 특징으로 하는 유기전기소자.The compound is an organic electric device, characterized in that included in at least one of the light emitting layer and the light emitting auxiliary layer.
  12. 제 8항에 있어서,The method of claim 8,
    상기 유기물층은 상기 양극 상에 순차적으로 형성된 정공수송층, 발광층 및 전자수송층을 포함하는 스택을 둘 이상 포함하는 것을 특징으로 하는 유기전기소자.The organic material layer comprises two or more stacks including a hole transport layer, an emission layer, and an electron transport layer sequentially formed on the anode.
  13. 제 12항에 있어서,The method of claim 12,
    상기 유기물층은 상기 둘 이상의 스택 사이에 형성된 전하생성층을 더 포함하는 것을 특징으로 하는 유기전기소자.The organic electroluminescent device further comprises a charge generation layer formed between the two or more stacks.
  14. 제8항의 유기전기소자를 포함하는 디스플레이장치; 및 A display device including the organic electric device of claim 8; And
    상기 디스플레이장치를 구동하는 제어부;를 포함하는 전자장치.Electronic device including; a control unit for driving the display device.
  15. 제 14항에 있어서,The method of claim 14,
    상기 유기전기소자는 유기전기발광소자, 유기태양전지, 유기감광체, 유기트랜지스터, 단색 조명용 소자 및 퀀텀닷 디스플레이용 소자로 이루어진 군에서 선택되는 것을 특징으로 하는 전자장치.The organic electric device is an electronic device, characterized in that 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.
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