WO2022225198A1 - Compound for organic electric element, organic electric element using same, and electronic device comprising same - Google Patents

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

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WO2022225198A1
WO2022225198A1 PCT/KR2022/003947 KR2022003947W WO2022225198A1 WO 2022225198 A1 WO2022225198 A1 WO 2022225198A1 KR 2022003947 W KR2022003947 W KR 2022003947W WO 2022225198 A1 WO2022225198 A1 WO 2022225198A1
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group
formula
integer
ring
aryl
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PCT/KR2022/003947
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French (fr)
Korean (ko)
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조석원
조민지
이선희
김대식
문성윤
염지은
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덕산네오룩스 주식회사
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Priority claimed from KR1020210057264A external-priority patent/KR20220146987A/en
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Priority to CN202280029789.6A priority Critical patent/CN117203184A/en
Publication of WO2022225198A1 publication Critical patent/WO2022225198A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
    • C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
    • 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
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof.
  • the organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material.
  • An organic electric device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween.
  • the organic layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • Efficiency, lifespan, and driving voltage are related to each other, and when the efficiency is increased, the driving voltage is relatively decreased. It shows a tendency to increase the lifespan.
  • the efficiency cannot be maximized simply by improving the organic material layer. This is because, when the energy level and T 1 value between each organic material layer, and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined, a long lifespan and high efficiency can be achieved at the same time. .
  • An object of the present invention is to provide a compound capable of lowering the driving voltage of a device and improving the luminous efficiency and lifespan of the 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 comprising the compound represented by the above formula.
  • 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 light emitting layer
  • second charge generation layer 420 second hole injection layer
  • aryl group and arylene group used in the present invention have 6 to 60 carbon atoms, respectively, unless otherwise specified, but are not limited thereto.
  • the aryl group or the arylene group may include a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, and the like.
  • fluorenyl group refers to a substituted or unsubstituted fluorenyl group
  • fluorenylene group refers to a substituted or unsubstituted fluorenyl group
  • the fluorenyl group or The fluorenylene group includes spiro compounds formed by bonding R and R' in the following structure, and also includes compounds in which adjacent R" is bonded to each other to form a ring.
  • Substituted fluorenyl group "substituted The fluorenylene group "means that at least one of R, R', and R” in the following structure is a substituent other than hydrogen, and in the formula below, R" may be 1 to 8.
  • R may be 1 to 8.
  • a fluorenyl group, a fluorenylene group, etc. may be described as a fluorene group, a fluorene ring group, or a fluorene group.
  • the term "spiro compound" has a 'spiro linkage', and the spiro linkage means a linkage formed by sharing only one atom between two rings. At this time, the atoms shared by the two rings are called 'spiro atoms', and depending on the number of spiro atoms in a compound, they are respectively 'monospiro-', 'dispiro-', 'trispiro-' ' It's called a compound.
  • heterocyclic group used in the present invention includes not only aromatic rings such as “heteroaryl group” or “heteroarylene group” but also non-aromatic rings, and unless otherwise specified, the number of carbon atoms each containing one or more heteroatoms It means a ring of 2 to 60, but is not limited thereto.
  • the heterocyclic group includes a monocyclic type including a heteroatom, a ring aggregate, a fused multiple ring system, a spiro compound, and the like.
  • aliphatic ring group used in the present invention refers to a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a monocyclic ring, a ring aggregate, a fused multiple ring system, a spiro compound, etc., and unless otherwise specified, the number of carbon atoms It means a ring of 3 to 60, but is not limited thereto. For example, even when benzene, which is an aromatic ring, and cyclohexane, which is a non-aromatic ring, are fused, it corresponds 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 substituents may be described as 'the name of the group reflecting the valence', but is described as 'name of the parent compound' You may.
  • the monovalent 'group' is 'phenanthryl'
  • the divalent group is 'phenanthrylene'. Regardless, it can also be described as the parent compound name, 'phenanthrene'.
  • pyrimidine regardless of the valence, it can be described as 'pyrimidine', or in the case of monovalent, as a pyrimidinyl group, in the case of divalent, as the 'name of the group' of the corresponding valence, such as pyrimidinylene. have.
  • the substituent R 1 means that it does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbons forming the benzene ring, and at this time, the indication of hydrogen bonded to carbon is shown. It can be omitted and the chemical formula or compound can be described.
  • R 1 when a is an integer of 1, one substituent R 1 is bonded to any one carbon of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it may be bonded as follows, for example, a is 4 to 6 Even if it is 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 as or different from each other.
  • the number in 'number-condensed ring' indicates the number of rings to be condensed.
  • 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 atom', such as a 5-membered ring, a 6-membered ring, etc., the number in 'number-atom' indicates the number of elements forming the ring.
  • thiophene or furan may correspond to a 5-membered ring
  • benzene or pyridine may correspond to a 6-membered ring.
  • the ring formed by bonding adjacent groups to each other is a C 6 ⁇ C 60 aromatic ring group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60
  • An aliphatic ring group may be selected from the group consisting of.
  • 'neighboring groups' refers to the following chemical formulas as an example, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 as well as R 7 and R 8 sharing one carbon are included, and non-adjacent ring structures such as R 1 and R 7 , R 1 and R 8 , or R 4 and R 5 , etc. Substituents bonded to elements (such as carbon or nitrogen) may also be included.
  • substituents on a ring constituent element such as carbon or nitrogen immediately adjacent to it, they may be a neighboring group, but if no substituent is bonded to a ring constituent element at the immediately adjacent position, it is bonded to the next ring constituent element It can be a group adjacent to a substituent group, and also substituents bonded to the same ring constituent carbon can be said to be adjacent groups.
  • substituents bonded to the same carbon as R 7 and R 8 in the following formula combine with each other to form a ring, a compound including a spiro moiety may be formed.
  • the expression 'neighboring groups may combine with each other to form a ring' is used in the same meaning as 'adjacent groups combine with each other to selectively form a ring', and at least one pair of It means a case where adjacent groups are bonded to each other to form a ring.
  • Each of the rings formed by bonding one group to each other is deuterium; halogen; an amino group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; 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; cyano group; nitro group; C 1 -
  • a component such as a layer, membrane, region, plate, etc.
  • 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 .
  • the light efficiency improving 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 improving layer 180 is formed The light efficiency of the organic electric device may be improved.
  • the light efficiency improving layer 180 may be formed on the second electrode 170 .
  • the light efficiency improving layer 180 is formed by the second electrode 170 .
  • the light efficiency improvement layer 180 serves as a buffer for the second electrode 170 . can do.
  • a buffer layer 210 or a light emitting auxiliary layer 220 may be further formed between the hole transport layer 130 and the light emitting layer 140 , which will be described with reference to FIG. 2 .
  • the 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 , It may include 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 , and a light efficiency improving layer 180 is formed on the second electrode.
  • 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 , and a light efficiency improving 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, a light emitting layer, and an electron transport layer are formed. This will be described with reference to FIG. 3 .
  • the organic electric device 300 includes two stacks ST1 and ST2 of an organic material layer formed of a multilayer between the first electrode 110 and the second electrode 170 . More than one set may be formed, and a charge generating layer (CGL) may be formed between stacks of organic material layers.
  • CGL charge generating layer
  • 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 the light efficiency improving 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 stacked structure or organic material layers having different stacked 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 generating layer CGL is formed between the first light emitting layer 340 and the second light emitting layer 440 to increase the efficiency of current generated in each light emitting layer and smoothly distribute charges.
  • the first light-emitting layer 340 may include a light-emitting material including a blue fluorescent dopant in a blue host, and the second light-emitting layer 440 includes a material in which a green host is doped with a greenish yellow dopant and a red dopant. may be included, but the material of the first light emitting layer 340 and the second light emitting layer 440 according to an embodiment of the present invention is not limited thereto.
  • n may be an integer of 1 to 5.
  • the charge generation layer CGL and the third stack may be additionally stacked on the second stack ST2 .
  • an organic electroluminescent device that emits white light by the mixing effect of the light emitted from each light emitting layer can be manufactured as well as light of various colors. It is also possible to manufacture an organic electroluminescent device that emits light.
  • the compound represented by Chemical 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 emitting auxiliary layer (220), an electron transport layer (150, 350, 450), the electron injection layer 160, the light emitting layers 140, 340, 440, or the light efficiency improving layer 180 may be used as a material, but preferably the hole transport layer 130, 330, 430, the light emission auxiliary layer 220 ) and/or may be used as a material of the light efficiency improving layer 180 .
  • the present invention by using the compound represented by Chemical Formula 1 as a material for the hole transport layers 130 , 330 , 430 , the light emitting auxiliary layer 220 and/or the light efficiency improving layer 180 , the energy level and T between each organic material layer By optimizing the value of 1 and the intrinsic properties of materials (mobility, interfacial properties, etc.), the lifespan and efficiency of the organic electric device can be improved at the same time.
  • the organic electroluminescent device may be manufactured using various deposition methods. It may be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form the anode 110, and the hole injection layer 120 thereon , after forming an organic material layer including the hole transport layer 130, the light emitting layer 140, the electron transport layer 150, and the electron injection layer 160, it can be prepared by depositing a material that can be used as the cathode 170 thereon. have.
  • a light emitting auxiliary layer 220 between the hole transport layer 130 and the light emitting layer 140 and an electron transport auxiliary layer (not shown) between the light emitting layer 140 and the electron transport layer 150 may be further formed. It can also be formed in a stack structure as shown.
  • the organic layer is a solution process or a solvent process rather than a deposition method using various polymer materials, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, Dr. Blay It can be manufactured with a smaller number of 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 formation method.
  • the organic electric device may be a top emission type, a back emission type, or a double side emission type depending on a 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/wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a navigation device, a game machine, various TV sets, and various computers.
  • the compound according to one aspect of the present invention is represented by the following formula (1).
  • the nitrogen N of the amine group may be bonded to the benzene ring moiety of the fluorene moiety, bonded to R', or bonded to R".
  • 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 P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; C 3 ⁇ C 60 aliphatic group; C 1 ⁇ C 20 Alkyl group; C 2 ⁇ C 20 Alkenyl group; C 2 ⁇ C 20 Alkynyl group; C 1 ⁇ C 20 Alkoxy group; C 6 ⁇ C 20 Aryloxy group; and -L′-N(R a )(R b ), and adjacent groups may be bonded to each other to form a ring.
  • a to c are each an integer of 0-4, d is an integer of 0-7, and when each of these 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 as or different from each other .
  • a+b may be an integer less than or equal to 7.
  • the ring is a C 6 ⁇ C 60 aromatic ring group ; fluorene ring group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60 It may be selected from the group consisting of an aliphatic cyclic group.
  • the aromatic ring is, for example, C 6 ⁇ C 20 , C 6 ⁇ C 18 , C 6 ⁇ C 16 , C 6 ⁇ C 14 , C 6 ⁇ C 13 , C 6 ⁇ C 12 , C 6 ⁇ C 10 , C 6 , C 10 , C 12 , C 14 , C 15 , C 16 , C 18 , etc.
  • C 6 ⁇ C 20 , C 6 ⁇ C 18 , C 6 ⁇ C 16 , C 6 ⁇ C 14 , C 6 ⁇ C 13 , C 6 ⁇ C 12 , C 6 ⁇ C 10 , C 6 , C 10 , C 12 , C 14 , C 15 , C 16 , C 18 , etc. may be, specifically, benzene, naphthalene, anthracene, phenanthrene, pyrene etc.
  • R' and R" are each independently hydrogen; C 6 ⁇ C 60 Aryl group; Fluorenyl group; C 2 ⁇ C 60 Heterocycle containing at least one heteroatom of O, N, S, Si and P group; C 3 ⁇ C 60 aliphatic ring group; C 1 ⁇ C 20 alkyl group; C 2 ⁇ C 20 alkenyl group; C 2 ⁇ C 20 alkynyl group; C 1 ⁇ C 20 alkoxy group; and C 6 -C 20 It is selected from the group consisting of an aryloxy group, and R' and R" may combine with each other to form a ring.
  • the nitrogen N of the amine group may be bonded to R' or R" of the fluorene moiety.
  • R' or R" is an aryl group
  • the nitrogen N of the amine group may be bonded to the aryl group.
  • a spiro compound When R' and R" combine with each other to form a ring, a spiro compound may be formed.
  • the ring is a C 6 ⁇ C 60 aromatic ring; fluorene ring group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; and C 3 to C 60 may be selected from the group consisting of an aliphatic cyclic group, and in particular, R' and R" may combine with each other to form a ring such as xanthenes, fluorenes, and acridines, for example, A ring comprising structure may be formed.
  • * corresponds to a spiro atom and shares a carbon atom with the fluorene to which R' and R" are bonded.
  • X is a direct bond
  • O, S, N(Ar 1 ) or C( R 1 ) (R 2 ) may be, and the structure is fluorene (a group) when X is a direct bond
  • 9 H when X is S -Thioxanthene when X is N(Ar 1 )
  • R' and R" are bonded to each other, resulting in spirobifluorene or its derivatives are formed.
  • R 1 and R 2 are 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; Phosphine oxide unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; siloxane group; cyano group; nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 Alkoxy group; C 6 -C 20 aryloxy group; C 6 -C 20 Arylthio group; C 1 -C 20 Alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkynyl group; C 6 -C 30 Aryl group; fluorenyl group; C 2 -C 30 A heterocyclic group comprising at least one heteroatom selected from the group consisting of O
  • the ring is a C 6 ⁇ C 60 aromatic ring group; fluorene ring group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60 May be selected from the group consisting of an aliphatic ring group, for example, when R 1 and R 2 are combined with each other to form a fluorene ring, spirobifluorene may be formed together with C to which they are bonded. have.
  • Ar 1 is a C 6 ⁇ C 30 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 30 A heterocyclic group; C 3 ⁇ C 30 of an aliphatic ring; and combinations thereof.
  • L is C 6 ⁇ C 60 Arylene group; fluorenylene group; C 3 ⁇ C 60 aliphatic group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; and combinations thereof.
  • Ar 1 is a C 6 ⁇ C 60 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; C 3 ⁇ C 60 aliphatic group; and combinations thereof.
  • Ar 1 may be a C 12 ⁇ C 25 aryl group or a fluorenyl group.
  • the L' is a single bond; C 6 ⁇ C 60 Arylene group; fluorenylene group; C 3 ⁇ C 60 aliphatic group; And O, N, S, Si and P including at least one heteroatom 2 ⁇ C 60 It is selected from the group consisting of a heterocyclic group.
  • the R a and R b are each independently of each other, independently of each other, a C 6 ⁇ C 60 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 60 A heterocyclic group; And C 3 ⁇ C 60 It is selected from the group consisting of an aliphatic cyclic group.
  • the aryl group is, for example, C 6 to C 30 , C 6 ⁇ C 29 , C 6 ⁇ C 28 , C 6 ⁇ C 27 , C 6 ⁇ C 26 , C 6 ⁇ C 25 , C 6 ⁇ C 24 , C 6 ⁇ C 23 , C 6 ⁇ C 22 , C 6 ⁇ C 21 , C 6 ⁇ C 20 , C 6 ⁇ C 19 , C 6 ⁇ C 18 , C 6 ⁇ C 17 , C 6 ⁇ C 16 , C 6 ⁇ C 15 , C 6 ⁇ C 14 , C 6 ⁇ C 13 , C 6 ⁇ C 12 , C 6 ⁇ C 11 , C 6 ⁇ C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C
  • the arylene group is, for example, C 6 ⁇ C 30 , C 6 ⁇ C 29 , C 6 ⁇ C 28 , C 6 ⁇ C 27 , C 6 ⁇ C 26 , C 6 ⁇ C 25 , C 6 ⁇ C 24 , C 6 ⁇ C 23 , C 6 ⁇ C 22 , C 6 ⁇ C 21 , C 6 ⁇ C 20 , C 6 ⁇ C 19 , C 6 ⁇ C 18 , C 6 ⁇ C 17 , C 6 ⁇ C 16 , C 6 ⁇ C 15 , C 6 ⁇ C 14 , C 6 ⁇ C 13 , C 6 ⁇ C 12 , C 6 ⁇ C 11 , C 6 ⁇ C 10 , C 6 , C It may be an arylene group such as 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , and specifically, phenylene, biphenyl, naph
  • the heterocyclic group is, for example, C 2 ⁇ C 30 , C 2 ⁇ C 29 , C 2 ⁇ C 28 , C 2 ⁇ C 27 , C 2 ⁇ C 26 , C 2 ⁇ C 25 , C 2 ⁇ C 24 , C 2 ⁇ C 23 , C 2 ⁇ C 22 , C 2 ⁇ C 21 , C 2 ⁇ C 20 , C 2 ⁇ C 19 , C 2 ⁇ C 18 , C 2 ⁇ C 17 , C 2 ⁇ C 16 , C 2 ⁇ C 15 , C 2 ⁇ C 14 , C 2 ⁇ C 13 , C 2 ⁇ C 12 , C 2 ⁇ C 11 , C 2 ⁇ C 10 , C 2 ⁇ C 9 , C 2 ⁇ C 8 , C 2 ⁇ C 7
  • At least one of R 1 to R 4 , Ar 1 , Ar 1 , R′, R′′, R 1 , R 2 , R a , R b is a fluorenyl group, or at least one of L and L′ is fluorenylene
  • the fluorenyl group or fluorenylene group is 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro [ Benzo[ b ]fluorene- 11,9' -fluorene], benzo[ b ]fluorene, 11,11-diphenyl-11H-benzo[ b ]fluorene, 9-(naphthalen-2-yl)9 -Phenyl -9H-fluorene, etc. may be used.
  • the aliphatic ring group is, for example, C 3 ⁇ C 30 , C 3 ⁇ C 29 , C 3 ⁇ C 28 , C 3 ⁇ C 27 , C 3 ⁇ C 26 , C 3 ⁇ C 25 , C 3 ⁇ C 24 , C 3 ⁇ C 23 , C 3 ⁇ C 22 , C 3 ⁇ C 21 , C 3 ⁇ C 20 , C 3 ⁇ C 19 , C 3 ⁇ C 18 , C 3 ⁇ C 17 , C 3 ⁇ C 16 , C 3 ⁇ C 15 , C 3 ⁇ C 14 , C 3 ⁇ C 13 , C 3 ⁇ C 12 , C 3 ⁇ C 11 , C 3 ⁇ C 10 , C 3 ⁇ C 8 , C 3 ⁇ C 6 , C
  • the alkyl group is, for example, C 1 to C 20 , C 1 to C 10 , C 1 to C 4 , C 1 , C 2 , C 3 , may be an alkylyl group such as C 4 , for example, a methyl group, an ethyl group, a t-butyl group, or the like.
  • the aryl group, an arylene group, a fluorenyl group, a fluorenylene group, a heterocyclic group, an aliphatic ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, a ring formed by bonding adjacent groups to each other, R A ring formed by bonding ' and R" to each other, and a ring formed by bonding R 1 and R 2 to each other are each deuterium; halogen; C 1 -C 20 alkyl group or C 6 -C 20 aryl group substituted or unsubstituted silane Group; C 1 -C 20 Alkyl group or C 6 -C 20 aryl group substituted or unsubstituted phosphine oxide; Siloxane group; Cyano group; Nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 Alkoxy group; C 6 -C 20 A
  • the aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, adjacent groups are bonded to each other
  • a ring formed by bonding to each other, a ring formed by combining R′ and R′′, and a ring formed by bonding to R 1 and R 2 are each deuterium; halogen; a C 1 -C 20 alkyl group or C 6 -C 20 aryl group substituted or an unsubstituted silane group; a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group substituted or unsubstituted phosphine oxide; a siloxane group; a cyano group; a nitro group; a C 1 -C 20 alkylthio group; C 1 -C 20 Alkoxy group; C
  • the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups are bonded to each other
  • the aryl group is, for example, C 6 ⁇ C 30 , C 6 ⁇ C 29 , C 6 ⁇ C 28 , C 6 ⁇ C 27 , C 6 ⁇ C 26 , C 6 ⁇ C 25 , C 6 ⁇ C 24 , C 6 ⁇ C 23 , C 6 ⁇ C 22 , C 6 ⁇ C 21 , C 6 ⁇ C 20 , C 6 ⁇ C 19 , C 6 ⁇ C 18 , C 6 ⁇ C 17 ,
  • the heterocyclic group is, for example, C 2 ⁇ C 30 , C 2 ⁇ C 29 , C 2 ⁇ C 28 , C 2 ⁇ C 27 , C 2 ⁇ C 26 , C 2 ⁇ C 25 , C 2 ⁇ C 24 , C 2 ⁇ C 23 , C 2 ⁇ C 22 , C 2 ⁇ C 21 , C 2 ⁇ C 20 , C 2 ⁇ C 19 , C 2 ⁇ C 18 , C 2 ⁇ C
  • the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups are bonded to each other
  • the fluorenyl group is 9,9-dimethyl -9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[ b ]fluorene-11,9'-fluorene], benzo[ b ]fluorene, 11,11-diphenyl- 11H -benzo[ b ]fluorene,
  • the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups are bonded to each other
  • the alkyl group is, for example, C 1 ⁇ C 20 , C 1 ⁇ C 10 , C 1 ⁇ C 4 , C 1 , C 2 , C 3 , may be an alkylyl group such as C 4 .
  • the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups are bonded to each other
  • the alkoxy group is, for example, C 1 ⁇ C 20 , C 1 ⁇ C 10 , C 1 ⁇ C 4 , C 1 , C 2 , C 3 , may be an alkoxy group such as C 4 .
  • the aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups are bonded to each other
  • the aliphatic ring group is, for example, C 3 ⁇ C 30 , C 3 ⁇ C 29 , C 3 ⁇ C 28 , C 3 ⁇ C 27 , C 3 ⁇ C 26 , C 3 ⁇ C 25 , C 3 ⁇ C 24 , C 3 ⁇ C 23 , C 3 ⁇ C 22 , C 3 ⁇ C 21 , C 3 ⁇ C 20 , C 3 ⁇ C 19 , C 3 ⁇ C 18 , C
  • Chemical Formula 1 may be represented by one of Chemical Formulas 2 to 22, and Chemical Formulas 7-1 to 10-1.
  • R 1 to R 4 , R', R", Ar 1 , L, a, c, and d are as defined in Formula 1, and * represents a bonding position.
  • * represents a bonding position.
  • an amine group may be bonded to the carbon indicated by *
  • a fluorene substituent may be bonded to the carbon indicated by *.
  • b is the same as defined in Formula 1, and in Formula 7, Formula 8, Formula 11, Formula 12, Formula 15 to Formula 18, Formula 7-1, and Formula 8-1, b is 0 to is an integer of 3, and in Formulas 9, 10, 13, 14, 19 to 22, Formulas 9-1 and 10-1, b is an integer of 0 to 4, and when b is an integer of 2 or more, R 2 Each is the same as or different from each other.
  • X is a direct bond, O, S, N(Ar 1 ) or C(R 1 )(R 2 ).
  • R 5 , R 6 , R 11 to R 15 , R 1 and R 2 are each independently hydrogen; heavy hydrogen; halogen; a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Phosphine oxide unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; siloxane group; cyano group; nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 Alkoxy group; C 6 -C 20 aryloxy group; C 6 -C 20 An arylthio group; C 1 -C 20 Alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkynyl group; C 6 -C 30 Aryl group; fluorenyl group; C 2 -C 30 A heterocyclic group comprising at least one heteroatom selected from the group
  • Neighboring groups for example, neighboring R 5 , neighboring R 6 , neighboring R 11 , neighboring R 12 , neighboring R 13 , neighboring R 14 , or neighboring R 15 are bonded to each other.
  • the ring is a C 6 ⁇ C 30 aromatic ring group; fluorene ring group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 30 A heterocyclic group; And C 3 ⁇ C 30 It may be selected from the group consisting of an aliphatic cyclic group.
  • the aromatic ring is, for example, C 6 ⁇ C 20 , C 6 ⁇ C 18 , C 6 ⁇ C 16 , C 6 ⁇ C 14 , C 6 ⁇ C 13 , C 6 ⁇ C 12 , C 6 ⁇ C 10 , C 6 , C 10 , C 12 , C 14 , C 15 , C 16 , C 18 , etc.
  • C 6 ⁇ C 20 , C 6 ⁇ C 18 , C 6 ⁇ C 16 , C 6 ⁇ C 14 , C 6 ⁇ C 13 , C 6 ⁇ C 12 , C 6 ⁇ C 10 , C 6 , C 10 , C 12 , C 14 , C 15 , C 16 , C 18 , etc. may be, specifically, benzene, naphthalene, anthracene, phenanthrene, pyrene etc.
  • a spiro compound When R 1 and R 2 combine with each other to form a ring, a spiro compound may be formed.
  • the ring is a C 6 ⁇ C 30 aromatic ring group; fluorene ring group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 30 A heterocyclic group; And C 3 ⁇ C 30 It may be selected from the group consisting of an aliphatic cyclic group.
  • the Ar 1 is a C 6 ⁇ C 30 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ⁇ C 30 A heterocyclic group; C 3 ⁇ C 30 of an aliphatic ring; and combinations thereof.
  • e is an integer of 0 to 5
  • e is an integer of 0 to 4
  • each of R 5 is each other same or different
  • each of R 6 , each of R 11 , R each of 12 , each of R 13 , each of R 14 and each of R 15 are the same as or different from each other.
  • Formulas 2 to 4 Formulas 7 to 14, and Formulas 7-1 to 10-1, d may be 0 or R 4 may be hydrogen.
  • R 1 to R 6 , R 11 and R 12 may be all hydrogen, or a to f, m, and n may all be 0.
  • the aryl group is, for example, C 6 -C 30 , C 6 -C 29 , C 6 -C 28 , C 6 ⁇ C 27 , C 6 ⁇ C 26 , C 6 ⁇ C 25 , C 6 ⁇ C 24 , C 6 ⁇ C 23 , C 6 ⁇ C 22 , C 6 ⁇ C 21 , C 6 ⁇ C 20 , C 6 ⁇ C 19 , C 6 ⁇ C 18 , C 6 ⁇ C 17 , C 6 ⁇ C 16 , C 6 ⁇ C 15 , C 6 ⁇ C 14 , C 6 ⁇ C 13 , C 6 ⁇ C 12 , C 6 ⁇ C 11 , C 6 ⁇ C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , may be an aryl group
  • the heterocyclic group is, for example, C 2 to C 30 , C 2 to C 29 , C 2 ⁇ C 28 , C 2 ⁇ C 27 , C 2 ⁇ C 26 , C 2 ⁇ C 25 , C 2 ⁇ C 24 , C 2 ⁇ C 23 , C 2 ⁇ C 22 , C 2 ⁇ C 21 , C 2 ⁇ C 20 , C 2 ⁇ C 19 , C 2 ⁇ C 18 , C 2 ⁇ C 17 , C 2 ⁇ C 16 , C 2 ⁇ C 15 , C 2 ⁇ C 14 , C 2 ⁇ C 13 , C 2 ⁇ C 12 , C 2 ⁇ C 11 , C 2 ⁇ C 10 , C 2 ⁇ C 9 , C 2 ⁇ C 8 , C 2 ⁇ C 7 , C 2 ⁇ C 6 , C 2 ⁇ C 5 ,
  • R 5 , R 6 , R 11 to R 15 , R 1 , R 2 , and Ar 1 is a fluorenyl group
  • the fluorenyl group or the fluorenylene group is 9,9-dimethyl-9H-flu Orene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[ b ]fluorene-11,9'-fluorene], benzo[ b ]fluorene , 11,11-diphenyl- 11H -benzo[ b ]fluorene, 9-(naphthalen-2-yl)9-phenyl- 9H -fluorene, and the like.
  • the aliphatic cyclic group is, for example, C 3 to C 30 , C 3 to C 29 , C 3 ⁇ C 28 , C 3 ⁇ C 27 , C 3 ⁇ C 26 , C 3 ⁇ C 25 , C 3 ⁇ C 24 , C 3 ⁇ C 23 , C 3 ⁇ C 22 , C 3 ⁇ C 21 , C 3 ⁇ C 20 , C 3 ⁇ C 19 , C 3 ⁇ C 18 , C 3 ⁇ C 17 , C 3 ⁇ C 16 , C 3 ⁇ C 15 , C 3 ⁇ C 14 , C 3 ⁇ C 13 , C 3 ⁇ C 12 , C 3 ⁇ C 11 , C 3 ⁇ C 10 , C 3 ⁇ C 8 , C 3 ⁇ C 6 , C 6 , C 10 , C 11 , C 12 , C
  • the alkyl group is, for example, C 1 to C 20 , C 1 to C 10 , C 1 to C 4 , C 1 , C 2 , C 3 , may be an alkylyl group such as C 4 , for example, a methyl group, an ethyl group, a t-butyl group, or the like.
  • R 5 , R 6 , R 11 To R 15 , R 1 , R 2 , Ar 1 , a ring formed by bonding adjacent groups to each other, R 1 and R 2 A ring formed by bonding to each other is 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; cyano group; nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 alkoxy group; C 6 -C 20 aryloxy group; C 6 -C 20 Arylthio group; C 1 -C 20 Alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkynyl group; C 6 -C 30 Aryl
  • the compound represented by Formula 1 may be one of the following compounds, but is not limited thereto.
  • the present invention provides a first electrode; a second electrode; It provides an organic electric device including an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a compound represented by Chemical Formula 1.
  • the organic material layer includes a light emitting layer, a hole transport layer formed between the light emitting layer and the first electrode, and a light emitting auxiliary layer formed between the hole transport layer and the first electrode, wherein the compound is at least one of the hole transport layer and the light emission auxiliary layer.
  • the organic electric device may further include a light efficiency improving layer containing the compound represented by Formula 1, wherein the light efficiency improving layer is formed on a layer that does not come into contact with the organic material layer among both surfaces of the first electrode or the second electrode. .
  • the organic material layer may include two or more stacks including a hole transport layer, a light emitting layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generating layer formed between the two or more stacks.
  • the present invention provides an electronic device including a display device including the organic electric device represented by Chemical Formula 1, and a controller for driving the display device.
  • the compound 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 the following compound, but is not limited thereto, and FD-MS (Field Desorption-Mass Spectrometry) values of the following compound are shown in Table 1.
  • Sub 2 of Scheme 1 may be synthesized by the reaction route as shown in Scheme 2 below, and Sub 2-I may be synthesized by Scheme 3 below, but is not limited thereto.
  • the compound belonging to Sub 2 may be a compound as follows, but is not limited thereto, and Table 2 shows FD-MS values of the following compounds.
  • N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4 on the ITO layer (anode) formed on the glass substrate -diamine (hereinafter abbreviated as 2-TNATA) was vacuum-deposited to a thickness of 60 nm to form a hole injection layer, and then the compound P1-1 of the present invention was vacuum-deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer was formed.
  • CBP 4,4'-N,N'-dicarbazole-biphenyl
  • Ir(ppy) 3 la tris(2-phenylpyridine)-iridium
  • BAlq (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum
  • BAlq 1,1'-biphenyl-4-olatobis(2-methyl-8-quinolinolato)aluminum
  • Alq 3 tris (8-quinolinol) aluminum
  • LiF was deposited on the electron transport layer to a thickness of 0.2 nm 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 P1-1 of the present invention as the hole transport layer material.
  • NPB N,N'-bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that one of the following comparative compounds ref 1 to ref 6 was used as the hole transport layer material instead of the compound P1-1 of the present invention.
  • Comparative compounds ref 1 to ref 6 are similar to the present invention in that all have a tertiary amine structure, but ref 1 and ref 2 are all amine groups substituted with pure aryl groups, whereas Chemical Formula 1 of the present invention is a fluorene moiety It is different in that the condensed ring including t is substituted, and ref 3 to ref 6 have a structure very similar to the compound of the present invention, but ref 3, ref 4 and ref 6 are linked to a linker L bonded to a phenylene moiety. It is different from the compound of the present invention in the bonding position of the naphthalene moiety, and ref 5 is different from the compound of the present invention in that L is not present.
  • configuration 1 the phenylene moiety directly bonded to L in Formula 1 of the present invention is referred to as configuration 1
  • the naphthalene moiety bonded to this configuration 1 is referred to as configuration 2.
  • the linker L and the configuration 2 are bonded to the phenylene of configuration 1 in an ortho position, whereas ref 3, ref 4, and ref 6 are linked to the linker L and the configuration 2 in the meta position. The difference is that they are connected.
  • a substituent containing a specific ring form fluorenyl group moiety, xanthene moiety, thioxanthene moiety, acridine moiety
  • a substituent containing a specific ring form fluorenyl group moiety, xanthene moiety, thioxanthene moiety, acridine moiety
  • the efficiency and lifetime are simultaneously improved while lowering the driving voltage.
  • the type of core and the type of substituents constituting the compound affect the electrical characteristics of the device.
  • the HOMO energy level values of the compounds P1-49, P2-25, P3-22, P5-16, and P5-17 of the present invention are higher than that of ref 1. This suggests that physical properties vary depending on the core structure of the compound, and when the compound represented by Formula 1 of the present invention is used as a material for the hole transport layer, holes can easily move from the hole injection layer to the light emitting layer, so the device compared to the ref 1 compound appears to have improved properties.
  • ref 3, ref 4 and ref 6 and the compounds P1-34, P1-49 and P5-16 of the present invention differ in the position where the linker L and the configuration 2 are bonded to the phenylene of configuration 1.
  • the compound of the present invention is easier to have a resonance structure compared to the comparative compound, it seems that the device characteristics of the Example using the compound of the present invention are improved.
  • the HOMO energy level of the compound P4-27 of the present invention is higher than ref 6, which shows that the presence or absence of a linking group affects the physical properties of the compound, and the HOMO energy level is high
  • the compound of the present invention is used as a material for the hole transport layer, since holes can easily move from the hole injection layer to the light emitting layer, it seems that the characteristics of the device are improved compared to ref 6 .
  • NPB was vacuum deposited on the hole injection layer to a thickness of 60 nm to form a hole transport layer.
  • the compound P1-2 of the present invention was vacuum-deposited to a thickness of 20 nm to form a light-emitting auxiliary layer, and then, 9,10-di(naphthalen-2-yl) as a host on the light-emitting auxiliary layer.
  • Anthracene and BD-052X manufactured by Idemitsu Kosan as a dopant were used in a weight ratio of 96:4 to form a light emitting layer with a thickness of 30 nm.
  • BAlq was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer
  • Alq 3 was vacuum deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer.
  • LiF was deposited on the electron transport layer to a thickness of 0.2 nm 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 28, except that the compound of the present invention described in Table 7 was used instead of the compound P1-2 of the present invention as a light emitting auxiliary layer material.
  • An organic electroluminescent device was manufactured in the same manner as in Example 28, except that the light-emitting auxiliary layer was not formed.
  • An organic electroluminescent device was manufactured in the same manner as in Example 28, except that one of ref 1 to ref 6 was used as the light emitting auxiliary layer material instead of the compound P1-2 of the present invention as shown in Table 7 below.
  • a forward bias DC voltage was applied to the organic electroluminescent devices of Examples 28 to 41 and Comparative Examples 8 to 14 prepared in this way, and electroluminescence (EL) characteristics were measured with a PR-650 manufactured by photoresearch. , at 500cd/m 2 standard luminance, the T95 lifespan was measured using the life measuring equipment of McScience. The measurement results are shown in Table 7 below.
  • the compound of the present invention when used as a material for the light-emitting auxiliary layer, the characteristics of the organic electric device are improved compared to the case where the light-emitting auxiliary layer is not formed or when one of the comparative compounds ref 1 to ref 6 is used. .
  • a specific ring-type substituent fluorene moiety, xanthene moiety, thioxanthene moiety, etc.
  • the compound of the present invention having the above-described characteristics is used as a hole transport layer material as well as light emission. It can be seen that the properties of the device are improved even when it is used as an auxiliary layer material.
  • the compound of the present invention improves the efficiency by better balancing the charge in the light emitting layer, and prevents electrons from passing through the light emitting layer, thereby maintaining the charge balance in the light emitting layer, thereby improving the driving voltage and lifespan.
  • the above-described characteristics of the compound of the present invention act as a major factor in improving the performance of the device.

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Abstract

The present invention provides: a compound represented by chemical formula 1; an organic electric 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 electric element. It is possible to lower the driving voltage of the organic electric element and improve the luminous efficiency and service life of the organic electric element by including the compound represented by chemical formula 1 in the organic layer thereof.

Description

유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치Compound for organic electric device, organic electric device 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 빛 에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기전기소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물 층은 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 emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy using an organic material. An organic electric device using an organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic material layer therebetween. Here, the organic layer is often formed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic electric device, and may include, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
유기 전기 발광소자에 있어 가장 문제시되는 것은 수명과 효율인데, 디스플레이가 대면적화되면서 이러한 효율이나 수명 문제는 반드시 해결해야 되는 상황이다.Lifespan and efficiency are the most problematic in organic electroluminescent devices, and as displays become larger, these problems of efficiency and lifespan must be solved.
효율과 수명, 구동전압 등은 서로 연관이 있으며, 효율이 증가되면 상대적으로 구동전압이 떨어지고, 구동전압이 떨어지면서 구동 시 발생하는 주울열(Joule heating)에 의한 유기물질의 결정화가 적어져 결과적으로 수명이 높아지는 경향을 나타낸다. 하지만, 유기물층을 단순히 개선한다고 하여 효율을 극대화시킬 수는 없다. 왜냐하면, 각 유기물층 간의 에너지 준위(energy level) 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 is relatively decreased. It shows a tendency to increase the lifespan. However, the efficiency cannot be maximized simply by improving the organic material layer. This is because, when the energy level and T 1 value between each organic material layer, and the intrinsic properties of the material (mobility, interfacial properties, etc.) are optimally combined, a long lifespan and high efficiency can be achieved at the same time. .
따라서, 유기전기소자가 갖는 우수한 특징들을 충분히 발휘하기 위해 소자 내 유기물층을 이루는 물질, 특히 정공수송층 및 발광보조층에 대한 개발이 필요하다.Therefore, in order to sufficiently exhibit the excellent characteristics of the organic electric device, it is necessary to develop a material constituting the organic layer in the device, in particular, a hole transport layer and a light emitting auxiliary layer.
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 the driving voltage of a device and improving the luminous efficiency and lifespan of the 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 PCTKR2022003947-appb-I000001
Figure PCTKR2022003947-appb-I000001
다른 측면에서, 본 발명은 상기 화학식으로 표시되는 화합물을 포함하는 유기전기소자 및 그 전자장치를 제공한다.In another aspect, the present invention provides an organic electric device and an electronic device comprising the compound represented by the above formula.
본 발명의 실시예에 따른 화합물을 이용함으로써 소자의 구동전압을 낮출 수 있고, 발광효율 및 수명을 향상시킬 수 있다.By using the compound according to the embodiment of the present invention, it is possible to lower the driving voltage of the device and improve the luminous efficiency and lifespan.
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 emitting auxiliary layer 320: first hole injection layer
330: 제1 정공수송층 340: 제1 발광층330: first hole transport layer 340: first light emitting 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 light emitting 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. The terms "aryl group" and "arylene group" used in the present invention have 6 to 60 carbon atoms, respectively, unless otherwise specified, but are not limited thereto. In the present invention, the aryl group or the arylene group may include a monocyclic type, a ring aggregate, a fused multiple ring system, a spiro compound, and the like.
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. "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 가수에 상관없이 플루오렌일기, 플루오렌일렌기 등을 플루오렌기, 플루오렌고리기 또는 플루오렌이라고 기재할 수도 있다.As used herein, the term "fluorenyl group" refers to a substituted or unsubstituted fluorenyl group, "fluorenylene group" refers to a substituted or unsubstituted fluorenyl group, and as used in the present invention, the fluorenyl group or The fluorenylene group includes spiro compounds formed by bonding R and R' in the following structure, and also includes compounds in which adjacent R" is bonded to each other to form a ring. "Substituted fluorenyl group", "substituted The fluorenylene group "means that at least one of R, R', and R" in the following structure is a substituent other than hydrogen, and in the formula below, R" may be 1 to 8. In the present specification, regardless of the valence A fluorenyl group, a fluorenylene group, etc. may be described as a fluorene group, a fluorene ring group, or a fluorene group.
Figure PCTKR2022003947-appb-I000002
Figure PCTKR2022003947-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.As used herein, the term "spiro compound" has a 'spiro linkage', and the spiro linkage means a linkage formed by sharing only one atom between two rings. At this time, the atoms shared by the two rings are called 'spiro atoms', and depending on the number of spiro atoms in a compound, they are respectively 'monospiro-', 'dispiro-', 'trispiro-' ' It's 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 탄소이외의 원소로서 예컨대 N, O, S, P 또는 Si 등을 나타내며, 고리를 형성하는 탄소 대신 하기 화합물과 같이 SO2, P=O 등과 같은 헤테로원자단을 포함할 수도 있다. 본 명세서에서 헤테로고리기는 헤테로원자를 포함하는 단일고리형, 고리집합체, 접합된 여러 고리계, 스파이로 화합물 등을 포함한다.The term "heterocyclic group" used in the present invention includes not only aromatic rings such as "heteroaryl group" or "heteroarylene group" but also non-aromatic rings, and unless otherwise specified, the number of carbon atoms each containing one or more heteroatoms It means a ring of 2 to 60, but is not limited thereto. As used herein, the term "heteroatom" refers to an element other than carbon, such as N, O, S, P or Si, unless otherwise specified, and instead of carbon forming a ring, as in the following compound, SO 2 , P= It may also contain a heteroatom group such as O. In the present specification, the heterocyclic group includes a monocyclic type including a heteroatom, a ring aggregate, a fused multiple ring system, a spiro compound, and the like.
Figure PCTKR2022003947-appb-I000003
Figure PCTKR2022003947-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 a cyclic hydrocarbon other than an aromatic hydrocarbon, and includes a monocyclic ring, a ring aggregate, a fused multiple ring system, a spiro compound, etc., and unless otherwise specified, the number of carbon atoms It means a ring of 3 to 60, but is not limited thereto. For example, even when benzene, which is an aromatic ring, and cyclohexane, which is a non-aromatic ring, are fused, it corresponds 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 substituents may be described as 'the name of the group reflecting the valence', but is described as 'name of the parent compound' You may. For example, in the case of 'phenanthrene', which is a type of aryl group, the monovalent 'group' is 'phenanthryl', and the divalent group is 'phenanthrylene'. Regardless, it can also be described as the parent compound name, 'phenanthrene'. Similarly, in the case of pyrimidine, regardless of the valence, it can be described as 'pyrimidine', or in the case of monovalent, as a pyrimidinyl group, in the case of divalent, as the 'name of the group' of the corresponding valence, such as 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, in describing the compound name or the substituent name, 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 and 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 the same as the definition of the substituent by the exponential definition of the following formula.
Figure PCTKR2022003947-appb-I000004
Figure PCTKR2022003947-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 it does not exist, that is, when a is 0, it means that all hydrogens are bonded to the carbons forming the benzene ring, and at this time, the indication of hydrogen bonded to carbon is shown. It can be omitted and the chemical formula or compound can be described. In addition, when a is an integer of 1, one substituent R 1 is bonded to any one carbon of the carbons forming the benzene ring, and when a is an integer of 2 or 3, it may be bonded as follows, for example, a is 4 to 6 Even if it is 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 as or different from each other.
Figure PCTKR2022003947-appb-I000005
Figure PCTKR2022003947-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 representing a condensed ring, the number in 'number-condensed ring' indicates the number of rings to be condensed. 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 present specification, when a ring is expressed in the form of a 'numeric atom', such as a 5-membered ring, a 6-membered ring, etc., the number in 'number-atom' indicates the number of elements forming the ring. For example, thiophene or furan may correspond to a 5-membered ring, and benzene or pyridine may correspond to a 6-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 specified in the present specification, the ring formed by bonding adjacent groups to each other is a C 6 ~ C 60 aromatic ring group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; And C 3 ~ C 60 An aliphatic ring group; may be selected from the group consisting of.
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. 하기 화학식에서 R7과 R8처럼 동일 탄소에 결합된 치환기가 서로 결합하여 고리를 형성할 경우에는 스파이로 모이어티가 포함된 화합물이 형성될 수 있다.In the present specification, unless otherwise specified, 'neighboring groups' refers to the following chemical formulas as an example, R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 as well as R 7 and R 8 sharing one carbon are included, and non-adjacent ring structures such as R 1 and R 7 , R 1 and R 8 , or R 4 and R 5 , etc. Substituents bonded to elements (such as carbon or nitrogen) may also be included. That is, if there is a substituent on a ring constituent element such as carbon or nitrogen immediately adjacent to it, they may be a neighboring group, but if no substituent is bonded to a ring constituent element at the immediately adjacent position, it is bonded to the next ring constituent element It can be a group adjacent to a substituent group, and also substituents bonded to the same ring constituent carbon can be said to be adjacent groups. When substituents bonded to the same carbon as R 7 and R 8 in the following formula combine with each other to form a ring, a compound including a spiro moiety may be formed.
Figure PCTKR2022003947-appb-I000006
,
Figure PCTKR2022003947-appb-I000007
Figure PCTKR2022003947-appb-I000006
,
Figure PCTKR2022003947-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 may combine with each other to form a ring' is used in the same meaning as 'adjacent groups combine with each other to selectively form a ring', and at least one pair of It means a case where adjacent groups are bonded to each other to form a ring.
또한, 본 명세서에서 다른 설명이 없는 한 아릴기, 아릴렌기, 플루오렌일기, 플루오렌일렌기, 헤테로고리기, 지방족 고리기, 알킬기, 알켄일기, 알킨일기, 알콕시기, 아릴옥시기, 및 이웃한 기끼리 서로 결합하여 형성된 고리는 각각 중수소; 할로겐; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 아미노기; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 실란기; C1-C20의 알킬기 또는 C6-C20의 아릴기로 치환 또는 비치환된 포스핀옥사이드; 실록산기; 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; 및 C3-C20의 지방족고리기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있다.In addition, unless otherwise specified herein, an aryl group, an arylene group, a fluorenyl group, a fluorenylene group, a heterocyclic group, an aliphatic ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, and neighboring Each of the rings formed by bonding one group to each other is deuterium; halogen; an amino group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; 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; cyano group; nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 Alkoxy group; C 6 -C 20 aryloxy group; C 6 -C 20 Arylthio 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 A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C 3 -C 20 It may be substituted with one or more substituents selected from the group consisting of an aliphatic ring group.
이하, 본 발명의 화합물이 포함된 유기전기소자의 적층구조에 대하여 도 1 내지 도 3을 참조하여 설명한다.Hereinafter, the laminated structure of the organic electric device containing the compound of the present invention will be described with reference to FIGS. 1 to 3 .
각 도면의 구성요소들에 참조부호를 부가함에 있어, 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 the components of each drawing, it should be noted that the same components are given the same reference numerals as much as possible even though 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 gist of the present invention, the 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 components of the present invention, terms such as first, second, A, B, (a), (b), etc. may be used. These terms are only for distinguishing the elements from other elements, and the essence, order, or order of the elements are not limited by the terms. When it is described that a component is “connected”, “coupled” or “connected” to another component, the component may be directly connected or connected to the other component, but another component is 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.Also, when a component, such as a layer, membrane, region, plate, etc., is said to be “on” or “on” another component, this means not only when it is “directly above” another component, but also when another component is in between. It should be understood that cases may be included. Conversely, it should be understood that when an element is said to be "on top of" 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, the light efficiency improving 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 improving layer 180 is formed The light efficiency of the organic electric device may 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 improving layer 180 may be formed on the second electrode 170 . In the case of a top emission organic light emitting device, the light efficiency improving layer 180 is formed by the second electrode 170 . ) can reduce optical energy loss due to surface plasmon polaritons (SPPs), and in the case of a bottom emission organic light emitting device, the light efficiency improvement layer 180 serves as a buffer 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 emitting auxiliary layer 220 may be further formed between the hole transport layer 130 and the light emitting layer 140 , which will be described with reference to FIG. 2 .
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 , the 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 , It may include 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 , and a light efficiency improving 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, a light emitting 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 , the organic electric device 300 according to another embodiment of the present invention includes two stacks ST1 and ST2 of an organic material layer formed of a multilayer between the first electrode 110 and the second electrode 170 . More than one set may be formed, and a charge generating layer (CGL) may be formed between 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 an 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 the light efficiency improving 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 such, the first stack and the second stack may be organic material layers having the same stacked structure or organic material layers having different stacked 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 generating layer CGL is formed between the first light emitting layer 340 and the second light emitting layer 440 to increase the efficiency of current generated in each light emitting layer and smoothly distribute 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 light-emitting layer 340 may include a light-emitting material including a blue fluorescent dopant in a blue host, and the second light-emitting layer 440 includes a material in which a green host is doped with a greenish yellow dopant and a red dopant. may be included, but the material of the first light emitting layer 340 and the second light emitting 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 to 5. When n is 2, the charge generation layer CGL and the 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 light emitting layers are formed by a multilayer stack structure method as shown in FIG. 3, an organic electroluminescent device that emits white light by the mixing effect of the light emitted from each light emitting layer can be manufactured as well as light of various colors. It is also possible to manufacture an organic electroluminescent device that emits light.
본 발명의 화학식 1로 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 정공수송층(130, 330, 430), 발광보조층(220) 또는/및 광효율 개선층(180)의 재료로 사용될 수 있다.The compound represented by Chemical 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 emitting auxiliary layer (220), an electron transport layer (150, 350, 450), the electron injection layer 160, the light emitting layers 140, 340, 440, or the light efficiency improving layer 180 may be used as a material, but preferably the hole transport layer 130, 330, 430, the light emission auxiliary layer 220 ) and/or may be used as a material of the light efficiency improving layer 180 .
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.A study on the selection of a core and a combination of sub-substituents bonded thereto because the band gap, electrical properties, interface properties, etc. may vary depending on which position the substituent is bonded to, even with the same and similar core In particular, long lifespan 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 the material (mobility, interfacial properties, etc.) are optimally combined.
따라서, 본 발명에서는 화학식 1로 표시되는 화합물을 정공수송층(130, 330, 430), 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 Chemical Formula 1 as a material for the hole transport layers 130 , 330 , 430 , the light emitting auxiliary layer 220 and/or the light efficiency improving layer 180 , the energy level and T between each organic material layer By optimizing the value of 1 and the intrinsic properties of materials (mobility, interfacial properties, etc.), the lifespan and efficiency of the organic electric device can be improved at the same time.
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 may be manufactured using a deposition method such as PVD or CVD, for example, by depositing a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form the anode 110, and the hole injection layer 120 thereon , after forming an organic material layer including the hole transport layer 130, the light emitting layer 140, the electron transport layer 150, and the electron injection layer 160, it can be prepared by depositing a material that can be used as the cathode 170 thereon. have. 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 layer is a solution process or a solvent process rather than a deposition method using various polymer materials, such as a spin coating process, a nozzle printing process, an inkjet printing process, a slot coating process, a dip coating process, a roll-to-roll process, Dr. Blay It can be manufactured with a smaller number of 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 formation 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 a top emission type, a back emission type, or a double side emission type depending on a 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, 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. In this case, the electronic device may be a current or future wired/wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a navigation device, a game machine, various TV sets, and various computers.
이하, 본 발명의 일 측면에 따른 화합물에 대하여 설명한다.Hereinafter, the compound according to an aspect of the present invention will be described.
본 발명의 일 측면에 따른 화합물은 하기 화학식 1로 표시된다.The compound according to one aspect of the present invention is represented by the following formula (1).
<화학식 1><Formula 1>
Figure PCTKR2022003947-appb-I000008
Figure PCTKR2022003947-appb-I000008
상기 화학식 1에서, 각 기호는 아래와 같이 정의될 수 있다.In Formula 1, each symbol may be defined as follows.
아민그룹의 질소 N은 플루오렌 모이어티의 벤젠고리 모이어티에 결합되거나 R'에 결합되거나, R"에 결합될 수 있다.The nitrogen N of the amine group may be bonded to the benzene ring moiety of the fluorene moiety, bonded to R', or bonded to R".
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~C20의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C20의 알콕시기; C6~C20의 아릴옥시기; 및 -L'-N(Ra)(Rb)로 이루어진 군에서 선택되고, 이웃한 기끼리 서로 결합하여 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 P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; C 3 ~ C 60 aliphatic group; C 1 ~ C 20 Alkyl group; C 2 ~ C 20 Alkenyl group; C 2 ~ C 20 Alkynyl group; C 1 ~ C 20 Alkoxy group; C 6 ~ C 20 Aryloxy group; and -L′-N(R a )(R b ), and adjacent groups may be bonded to each other to form a ring.
a 내지 c는 각각 0~4의 정수이고, d는 0~7의 정수이고, 이들 각각이 2 이상의 정수인 경우, R1 각각, R2 각각, R3 각각, R4 각각은 서로 같거나 상이하다. 아민그룹의 질소 N이 플루오렌 모이어티의 벤젠고리 모이어티에 결합될 경우, a+b는 7하의 정수일 수 있다.a to c are each an integer of 0-4, d is an integer of 0-7, and when each of these 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 as or different from each other . When the nitrogen N of the amine group is bonded to the benzene ring moiety of the fluorene moiety, a+b may be an integer less than or equal to 7.
이웃한 기끼리, 예컨대 이웃한 R1끼리, 이웃한 R2끼리, 이웃한 R3끼리 또는 이웃한 R4끼리 서로 결합하여 고리를 형성할 경우, 상기 고리는 C6~C60의 방향족고리기; 플루오렌고리기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 C3~C60의 지방족고리기로 이루어진 군에서 선택될 수 있다.When neighboring groups, for example, neighboring R 1 , neighboring R 2 , neighboring R 3 , or neighboring R 4 are bonded to each other to form a ring, the ring is a C 6 ~ C 60 aromatic ring group ; fluorene ring group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; And C 3 ~ C 60 It may be selected from the group consisting of an aliphatic cyclic group.
이웃한 기끼리 서로 결합하여 방향족고리를 형성할 경우, 상기 방향족고리는 예컨대, C6~C20, C6~C18, C6~C16, C6~C14, C6~C13, C6~C12, C6~C10, C6, C10, C12, C14, C15, C16, C18 등일 수 있고, 구체적으로, 벤젠, 나프탈렌, 안트라센, 페난트렌, 파이렌 등일 수 있다.When adjacent groups are bonded to each other to form an aromatic ring, the aromatic ring is, for example, C 6 ~ C 20 , C 6 ~ C 18 , C 6 ~ C 16 , C 6 ~ C 14 , C 6 ~ C 13 , C 6 ~ C 12 , C 6 ~ C 10 , C 6 , C 10 , C 12 , C 14 , C 15 , C 16 , C 18 , etc. may be, specifically, benzene, naphthalene, anthracene, phenanthrene, pyrene etc.
R' 및 R"은 서로 독립적으로 수소; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; C1~C20의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C20의 알콕시기; 및 C6~C20의 아릴옥시기로 이루어진 군에서 선택되고, R'과 R"이 서로 결합하여 고리를 형성할 수 있다. 아민그룹의 질소 N은 플루오렌 모이어티의 R' 또는 R"에 결합될 수 있는데, 예컨대, R' 또는 R"이 아릴기인 경우, 상기 아릴기에 아민그룹의 질소 N이 결합될 수 있다.R' and R" are each independently hydrogen; C 6 ~ C 60 Aryl group; Fluorenyl group; C 2 ~ C 60 Heterocycle containing at least one heteroatom of O, N, S, Si and P group; C 3 ~ C 60 aliphatic ring group; C 1 ~ C 20 alkyl group; C 2 ~ C 20 alkenyl group; C 2 ~ C 20 alkynyl group; C 1 ~ C 20 alkoxy group; and C 6 -C 20 It is selected from the group consisting of an aryloxy group, and R' and R" may combine with each other to form a ring. The nitrogen N of the amine group may be bonded to R' or R" of the fluorene moiety. For example, when R' or R" is an aryl group, the nitrogen N of the amine group may be bonded to the aryl group.
R'과 R"이 서로 결합하여 고리를 형성할 경우, 스파이로 화합물이 형성될 수 있다. 예컨대, R'과 R"이 서로 결합하여 고리를 형성할 경우, 상기 고리는 C6~C60의 방향족고리기; 플루오렌고리기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 C3~C60의 지방족고리기로 이루어진 군에서 선택될 수 있으며, 특히 R'과 R"이 서로 결합하여 잔텐류, 플루오렌류, 아크리딘류 등의 고리를 형성할 수 있는데, 예컨대, 아래 구조를 포함하는 고리가 형성될 수 있다.When R' and R" combine with each other to form a ring, a spiro compound may be formed. For example, when R' and R" combine with each other to form a ring, the ring is a C 6 ~ C 60 aromatic ring; fluorene ring group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; and C 3 to C 60 may be selected from the group consisting of an aliphatic cyclic group, and in particular, R' and R" may combine with each other to form a ring such as xanthenes, fluorenes, and acridines, for example, A ring comprising structure may be formed.
Figure PCTKR2022003947-appb-I000009
Figure PCTKR2022003947-appb-I000009
상기 구조에서, *는 스파이로 원자에 해당하는 것으로 R'과 R"이 결합된 플루오렌과 탄소원자를 서로 공유한다. 상기 구조에서 X는 직접결합, O, S, N(Ar1) 또는 C(R1)(R2)가 될 수 있으며, 상기 구조는 X가 직접결합인 경우는 플루오렌(일기), X가 O인 경우는 9H-잔텐(xanthene), X가 S인 경우는 9H-싸이오잔텐(thioxanthene), X가 N(Ar1)인 경우는 아크리딘 또는 그 유도체에 해당하며, X가 직접결합인 경우 R'과 R"이 서로 결합하여 결과적으로 스파이로바이플루오렌이나 그 유도체가 형성된다.In the above structure, * corresponds to a spiro atom and shares a carbon atom with the fluorene to which R' and R" are bonded. In the above structure, X is a direct bond, O, S, N(Ar 1 ) or C( R 1 ) (R 2 ) may be, and the structure is fluorene (a group) when X is a direct bond, 9 H -xanthene when X is O, 9 H when X is S -Thioxanthene, when X is N(Ar 1 ), corresponds to acridine or a derivative thereof, and when X is a direct bond, R' and R" are bonded to each other, resulting in spirobifluorene or its derivatives are formed.
C(R1)(R2)에서, R1 및 R2는 서로 독립적으로 수소; 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; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C30의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C30의 헤테로고리기; C3-C30의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택되며, R1과 R2는 서로 결합하여 고리를 형성할 수 있다. In C(R 1 )(R 2 ), R 1 and R 2 are 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; Phosphine oxide unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; siloxane group; cyano group; nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 Alkoxy group; C 6 -C 20 aryloxy group; C 6 -C 20 Arylthio group; C 1 -C 20 Alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkynyl group; C 6 -C 30 Aryl group; fluorenyl group; C 2 -C 30 A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C 30 An aliphatic group; and combinations thereof, and R 1 and R 2 may be bonded to each other to form a ring.
R1과 R2가 서로 결합하여 고리를 형성할 경우, 상기 고리는 C6~C60의 방향족고리기; 플루오렌고리기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 C3~C60의 지방족고리기로 이루어진 군에서 선택될 수 있으며, 예컨대, R1과 R2가 서로 결합하여 플루오렌 고리를 형성하면 이들이 결합된 C와 함께 스파이로바이플루오렌이 형성될 수 있다.When R 1 and R 2 are bonded to each other to form a ring, the ring is a C 6 ~ C 60 aromatic ring group; fluorene ring group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; And C 3 ~ C 60 May be selected from the group consisting of an aliphatic ring group, for example, when R 1 and R 2 are combined with each other to form a fluorene ring, spirobifluorene may be formed together with C to which they are bonded. have.
N(Ar1)에서, Ar1은 C6~C30의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C30의 헤테로고리기; C3~C30의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택된다.In N(Ar 1 ), Ar 1 is a C 6 ~ C 30 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 30 A heterocyclic group; C 3 ~ C 30 of an aliphatic ring; and combinations thereof.
L은 C6~C60의 아릴렌기; 플루오렌일렌기; C3~C60의 지방족고리기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 이들의 조합으로 이루어진 군에서 선택된다.L is C 6 ~ C 60 Arylene group; fluorenylene group; C 3 ~ C 60 aliphatic group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; and combinations thereof.
Ar1은 C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택된다. 예컨대, Ar1은 C12~C25의 아릴기 또는 플루오렌일기일 수 있다.Ar 1 is a C 6 ~ C 60 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; C 3 ~ C 60 aliphatic group; and combinations thereof. For example, Ar 1 may be a C 12 ~ C 25 aryl group or a fluorenyl group.
상기 L'은 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 선택된다.The L' is a single bond; C 6 ~ C 60 Arylene group; fluorenylene group; C 3 ~ C 60 aliphatic group; And O, N, S, Si and P including at least one heteroatom 2 ~ C 60 It is selected from the group consisting of a heterocyclic group.
상기 Ra 및 Rb는 서로 독립적으로 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 선택된다.The R a and R b are each independently of each other, independently of each other, a C 6 ~ C 60 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; And C 3 ~ C 60 It is selected from the group consisting of an aliphatic cyclic group.
상기 R1 내지 R4, Ar1, Ar1, R', R", R1, R2, Ra, Rb 중에서 적어도 하나가 아릴기인 경우, 상기 아릴기는 예컨대, C6~C30, C6~C29, C6~C28, C6~C27, C6~C26, C6~C25, C6~C24, C6~C23, C6~C22, C6~C21, C6~C20, C6~C19, C6~C18, C6~C17, C6~C16, C6~C15, C6~C14, C6~C13, C6~C12, C6~C11, C6~C10, C6, C10, C12, C13, C14, C15, C16, C17, C18 등의 아릴기일 수 있고, 구체적으로, 페닐, 바이페닐, 나프틸, 터페닐, 페난트렌, 트리페닐렌 등일 수 있다.When at least one of R 1 to R 4 , Ar 1 , Ar 1 , R′, R″, R 1 , R 2 , R a , R b is an aryl group, the aryl group is, for example, C 6 to C 30 , C 6 ~C 29 , C 6 ~C 28 , C 6 ~C 27 , C 6 ~C 26 , C 6 ~C 25 , C 6 ~C 24 , C 6 ~C 23 , C 6 ~C 22 , C 6 ~ C 21 , C 6 ~C 20 , C 6 ~C 19 , C 6 ~C 18 , C 6 ~C 17 , C 6 ~C 16 , C 6 ~C 15 , C 6 ~C 14 , C 6 ~C 13 , C 6 ~ C 12 , C 6 ~ C 11 , C 6 ~ C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 may be an aryl group and, specifically, may be phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, triphenylene, and the like.
상기 L, L' 중에서 적어도 하나가 아릴렌기인 경우, 상기 아릴렌기는 예컨대, C6~C30, C6~C29, C6~C28, C6~C27, C6~C26, C6~C25, C6~C24, C6~C23, C6~C22, C6~C21, C6~C20, C6~C19, C6~C18, C6~C17, C6~C16, C6~C15, C6~C14, C6~C13, C6~C12, C6~C11, C6~C10, C6, C10, C12, C13, C14, C15, C16, C17, C18 등의 아릴렌기일 수 있고, 구체적으로, 페닐렌, 바이페닐, 나프틸렌, 터페닐, 페난트렌, 트리페닐렌 등일 수 있다.When at least one of L and L' is an arylene group, the arylene group is, for example, C 6 ~ C 30 , C 6 ~ C 29 , C 6 ~ C 28 , C 6 ~ C 27 , C 6 ~ C 26 , C 6 ~C 25 , C 6 ~C 24 , C 6 ~C 23 , C 6 ~C 22 , C 6 ~C 21 , C 6 ~C 20 , C 6 ~C 19 , C 6 ~C 18 , C 6 ~C 17 , C 6 ~C 16 , C 6 ~C 15 , C 6 ~C 14 , C 6 ~C 13 , C 6 ~C 12 , C 6 ~C 11 , C 6 ~C 10 , C 6 , C It may be an arylene group such as 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , and specifically, phenylene, biphenyl, naphthylene, terphenyl, phenanthrene, triphenyl Ren or the like.
상기 R1 내지 R4, Ar1, Ar1, R', R", R1, R2, Ra, Rb, L, L' 중에서 적어도 하나가 헤테로고리기인 경우, 상기 헤테로고리기는 예컨대, C2~C30, C2~C29, C2~C28, C2~C27, C2~C26, C2~C25, C2~C24, C2~C23, C2~C22, C2~C21, C2~C20, C2~C19, C2~C18, C2~C17, C2~C16, C2~C15, C2~C14, C2~C13, C2~C12, C2~C11, C2~C10, C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29 등의 헤테로고리기일 수 있고, 구체적으로, 피리딘, 피리미딘, 피라진, 피리다진, 트리아진, 퓨란, 피롤, 실롤, 인덴, 인돌, 페닐-인돌, 벤조인돌, 페닐-벤조인돌, 피라지노인돌, 퀴놀린, 아이소퀴놀린, 벤조퀴놀린, 피리도퀴놀린, 퀴나졸린, 벤조퀴나졸린, 다이벤조퀴나졸린, 페난트로퀴나졸린, 퀴녹살린, 벤조퀴녹살린, 다이벤조퀴녹살린, 벤조퓨란, 나프토벤조퓨란, 다이벤조퓨란, 다이나프토퓨란, 싸이오펜, 벤조싸이오펜, 다이벤조싸이오펜, 나프토벤조싸이이오펜, 다이나프토싸이오펜, 카바졸, 페닐-카바졸, 벤조카바졸, 페닐-벤조카바졸, 나프틸-벤조카바졸, 다이벤조카바졸, 인돌로카바졸, 벤조퓨로피리딘, 벤조싸이에노피리딘, 벤조퓨로피리딘, 벤조싸이에노피리미딘, 벤조퓨로피리미딘, 벤조싸이에노피라진, 벤조퓨로피라진, 벤조이미다졸, 벤조티아졸, 벤조옥사졸, 벤조실롤, 페난트롤린, 다이하이드로-페닐페나진, 10-페닐-10H-페녹사진, 페녹사진, 페노싸이아진, 다이벤조다이옥신, 벤조다이벤조다이옥신, 싸이안트렌, 9,9-다이메틸-9H-잔쓰렌, 9,9-다이메틸-9H-싸이옥잔쓰렌, 다이하이드로다이메틸페닐아크리딘, 스파이로[플루오렌-9,9'-잔텐] 등일 수 있다.When at least one of R 1 to R 4 , Ar 1 , Ar 1 , R', R", R 1 , R 2 , R a , R b , L, L' is a heterocyclic group, the heterocyclic group is, for example, C 2 ~C 30 , C 2 ~C 29 , C 2 ~C 28 , C 2 ~C 27 , C 2 ~C 26 , C 2 ~C 25 , C 2 ~C 24 , C 2 ~C 23 , C 2 ~C 22 , C 2 ~C 21 , C 2 ~C 20 , C 2 ~C 19 , C 2 ~C 18 , C 2 ~C 17 , C 2 ~C 16 , C 2 ~C 15 , C 2 ~C 14 , C 2 ~C 13 , C 2 ~C 12 , C 2 ~C 11 , C 2 ~C 10 , C 2 ~C 9 , C 2 ~C 8 , C 2 ~C 7 , C 2 ~C 6 , C 2 ~C 5 , C 2 ~C 4 , C 2 ~C 3 , C 2 , C 3 , C 4 , C 5 , C 6 , C 7 , C 8 , C 9 , C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , C 25 , C 26 , C 27 , C 28 , C 29 may be a heterocyclic group, and specifically, pyridine, pyrimidine, pyrazine, pyridazine, triazine, furan, pyrrole, silol, indene, indole, phenyl-indole, benzoindole, phenyl-benzoindole, pyrazinoindole , quinoline, isoquinoline, benzoquinoline, pyridoquinoline, quinazoline, benzoquinazoline, dibenzoquinazoline, phenanthroquinazoline, quinoxaline, benzoquinoxaline, dibenzoquinoxaline, benzofuran, naphthobenzofuran, Dibenzofuran, dinaphthofuran, thiophene, benzothiophene, dibenzothiophene, naphthobenzothiophene, dinaphthothiophene, carbazole, phenyl-carbazole, benzocarbazole, phenyl-benzocarbazole, naph Thiyl-benzocarbazole, dibenzocarbazole, indolocarbazole, benzofuropyridine, benzothienopyridine, benzofuropyridine, benzothienopyrimidine, benzofuropyrimidine, ben Zothienopyrazine, benzofuropyrazine, benzoimidazole, benzothiazole, benzoxazole, benzosilol, phenanthroline, dihydro-phenylphenazine, 10-phenyl-10H-phenoxazine, phenoxazine, pheno Thiazine, dibenzodioxin, benzodibenzodioxin, cyanthrene, 9,9-dimethyl-9H-xanthrene, 9,9-dimethyl-9H-thioxanthrene, dihydrodimethylphenylacridine, spy rho[fluorene-9,9'-xanthene] and the like.
상기 R1 내지 R4, Ar1, Ar1, R', R", R1, R2, Ra, Rb 중에서 적어도 하나가 플루오렌일기이거나, L, L' 중에서 적어도 하나가 플루오렌일렌기인 경우, 상기 플루오렌일기 또는 플루오렌일렌기는 9,9-다이메틸-9H-플루오렌, 9,9-다이페닐-9H-플루오렌, 9,9'-스파이로바이플루오렌, 스파이로[벤조[b]플루오렌-11,9'-플루오렌], 벤조[b]플루오렌, 11,11-다이페닐-11H-벤조[b]플루오렌, 9-(나프탈렌-2-일)9-페닐-9H-플루오렌 등일 수 있다.At least one of R 1 to R 4 , Ar 1 , Ar 1 , R′, R″, R 1 , R 2 , R a , R b is a fluorenyl group, or at least one of L and L′ is fluorenylene In the case of a group, the fluorenyl group or fluorenylene group is 9,9-dimethyl-9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro [ Benzo[ b ]fluorene- 11,9' -fluorene], benzo[ b ]fluorene, 11,11-diphenyl-11H-benzo[ b ]fluorene, 9-(naphthalen-2-yl)9 -Phenyl -9H-fluorene, etc. may be used.
상기 R1 내지 R4, Ar1, Ar1, R', R", R1, R2, Ra, Rb, L, L' 중에서 적어도 하나가 지방족고리기인 경우, 상기 지방족고리기는 예컨대, C3~C30, C3~C29, C3~C28, C3~C27, C3~C26, C3~C25, C3~C24, C3~C23, C3~C22, C3~C21, C3~C20, C3~C19, C3~C18, C3~C17, C3~C16, C3~C15, C3~C14, C3~C13, C3~C12, C3~C11, C3~C10, C3~C8, C3~C6, C6, C10, C11, C12, C13, C14, C15, C16, C17, C18 등의 지방족고리기일 수 있고, 구체적으로, 사이클로헥산일기, 아다만틸기 등일 수 있다.When at least one of R 1 to R 4 , Ar 1 , Ar 1 , R', R", R 1 , R 2 , R a , R b , L, L' is an aliphatic ring group, the aliphatic ring group is, for example, C 3 ~C 30 , C 3 ~C 29 , C 3 ~C 28 , C 3 ~C 27 , C 3 ~C 26 , C 3 ~C 25 , C 3 ~C 24 , C 3 ~C 23 , C 3 ~C 22 , C 3 ~C 21 , C 3 ~C 20 , C 3 ~C 19 , C 3 ~C 18 , C 3 ~C 17 , C 3 ~C 16 , C 3 ~C 15 , C 3 ~C 14 , C 3 ~C 13 , C 3 ~C 12 , C 3 ~C 11 , C 3 ~C 10 , C 3 ~C 8 , C 3 ~C 6 , C 6 , C 10 , C 11 , C 12 , It may be an aliphatic ring group such as C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , and specifically, a cyclohexanyl group, an adamantyl group, and the like.
상기 R1 내지 R4, R', R", R1, R2 중에서 적어도 하나가 알킬기인 경우, 상기 알킬기는 예컨대, C1~C20, C1~C10, C1~C4, C1, C2, C3, C4 등의 알킬일기일 수 있고, 예컨대, 메틸기, 에틸기, t-부틸기 등일 수 있다.When at least one of R 1 to R 4 , R′, R″, R 1 , and R 2 is an alkyl group, the alkyl group is, for example, C 1 to C 20 , C 1 to C 10 , C 1 to C 4 , C 1 , C 2 , C 3 , may be an alkylyl group such as C 4 , for example, a methyl group, an ethyl group, a t-butyl group, or the like.
상기 아릴기, 아릴렌기, 플루오렌일기, 플루오렌일렌기, 헤테로고리기, 지방족 고리기, 알킬기, 알켄일기, 알킨일기, 알콕시기, 아릴옥시기, 이웃한 기끼리 서로 결합하여 형성된 고리, R'과 R"이 서로 결합하여 형성된 고리, R1과 R2가 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; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C30의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C30의 헤테로고리기; C3-C30의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있다.The aryl group, an arylene group, a fluorenyl group, a fluorenylene group, a heterocyclic group, an aliphatic ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, a ring formed by bonding adjacent groups to each other, R A ring formed by bonding ' and R" to each other, and a ring formed by bonding R 1 and R 2 to each other are each deuterium; halogen; C 1 -C 20 alkyl group or C 6 -C 20 aryl group substituted or unsubstituted silane Group; C 1 -C 20 Alkyl group or C 6 -C 20 aryl group substituted or unsubstituted phosphine oxide; Siloxane group; Cyano group; Nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 Alkoxy group; C 6 -C 20 Aryloxy group; C 6 -C 20 Arylthio group; C 1 -C 20 Alkyl group; C 2 -C 20 Alkenyl group; C 2 -C 20 Alkynyl group C 6 -C 30 Aryl group; Fluorenyl group; C 2 -C 30 Heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C It may be substituted with one or more substituents selected from the group consisting of an aliphatic ring group of 30 ;
바람직하게는, 상기 아릴기, 아릴렌기, 플루오렌일기, 플루오렌일렌기, 헤테로고리기, 지방족 고리기, 알킬기, 알켄일기, 알킨일기, 알콕시기, 아릴옥시기, 이웃한 기끼리 서로 결합하여 형성된 고리, R'과 R"이 서로 결합하여 형성된 고리, R1과 R2가 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; 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; 및 이들의 조합으로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있다.Preferably, the aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, adjacent groups are bonded to each other A ring formed by bonding to each other, a ring formed by combining R′ and R″, and a ring formed by bonding to R 1 and R 2 are each deuterium; halogen; a C 1 -C 20 alkyl group or C 6 -C 20 aryl group substituted or an unsubstituted silane group; a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group substituted or unsubstituted phosphine oxide; a siloxane group; a cyano group; a nitro group; a C 1 -C 20 alkylthio group; C 1 -C 20 Alkoxy group; C 6 -C 20 Aryloxy group; C 6 -C 20 Arylthio 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; It may be substituted with one or more substituents selected from the group consisting of a C 3 -C 20 aliphatic ring group, and combinations thereof.
상기 아릴기, 플루오렌일기, 헤테로고리기, 지방족고리기, 방향족고리기, 알킬기, 알켄일기, 알킨일기, 알콕시기, 아릴옥시기, 아릴렌기, 플루오렌일렌기, 및 이웃한 기끼리 서로 결합하여 형성된 고리, R'과 R"이 서로 결합하여 형성된 고리, R1과 R2가 서로 결합하여 형성된 고리 중에서 적어도 하나가 아릴기로 치환될 경우, 상기 아릴기는 예컨대 C6~C30, C6~C29, C6~C28, C6~C27, C6~C26, C6~C25, C6~C24, C6~C23, C6~C22, C6~C21, C6~C20, C6~C19, C6~C18, C6~C17, C6~C16, C6~C15, C6~C14, C6~C13, C6~C12, C6~C11, C6~C10, C6, C10, C12, C13, C14, C15, C16, C17, C18 등의 아릴기일 수 있다.The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups are bonded to each other When at least one of the ring formed by the above, the ring formed by combining R' and R", and the ring formed by combining R 1 and R 2 with each other is substituted with an aryl group, the aryl group is, for example, C 6 ~ C 30 , C 6 ~ C 29 , C 6 ~C 28 , C 6 ~C 27 , C 6 ~C 26 , C 6 ~C 25 , C 6 ~C 24 , C 6 ~C 23 , C 6 ~C 22 , C 6 ~C 21 , C 6 ~C 20 , C 6 ~C 19 , C 6 ~C 18 , C 6 ~C 17 , C 6 ~C 16 , C 6 ~C 15 , C 6 ~C 14 , C 6 ~C 13 , C 6 ~ C 12 , C 6 ~ C 11 , C 6 ~ C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 may be an aryl group.
상기 아릴기, 플루오렌일기, 헤테로고리기, 지방족고리기, 방향족고리기, 알킬기, 알켄일기, 알킨일기, 알콕시기, 아릴옥시기, 아릴렌기, 플루오렌일렌기, 및 이웃한 기끼리 서로 결합하여 형성된 고리, R'과 R"이 서로 결합하여 형성된 고리, R1과 R2가 서로 결합하여 형성된 고리 중에서 적어도 하나가 헤테로고리기로 치환될 경우, 상기 헤테로고리기는 예컨대 C2~C30, C2~C29, C2~C28, C2~C27, C2~C26, C2~C25, C2~C24, C2~C23, C2~C22, C2~C21, C2~C20, C2~C19, C2~C18, C2~C17, C2~C16, C2~C15, C2~C14, C2~C13, C2~C12, C2~C11, C2~C10, C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29 등의 헤테로고리기일 수 있다.The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups are bonded to each other When at least one of the ring formed by the above, a ring formed by combining R' and R", and a ring formed by combining R 1 and R 2 with each other is substituted with a heterocyclic group, the heterocyclic group is, for example, C 2 ~ C 30 , C 2 ~C 29 , C 2 ~C 28 , C 2 ~C 27 , C 2 ~C 26 , C 2 ~C 25 , C 2 ~C 24 , C 2 ~C 23 , C 2 ~C 22 , C 2 ~ C 21 , C 2 ~C 20 , C 2 ~C 19 , C 2 ~C 18 , C 2 ~C 17 , C 2 ~C 16 , C 2 ~C 15 , C 2 ~C 14 , C 2 ~C 13 , C 2 ~C 12 , C 2 ~C 11 , C 2 ~C 10 , C 2 ~C 9 , C 2 ~C 8 , C 2 ~C 7 , C 2 ~C 6 , C 2 ~C 5 , C 2 toC 4 , C 2 to C 3 , C 2 , C 3 , C 4 , C 5 , C 6 , C 7 , C 8 , C 9 , C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , C 25 , C 26 , C 27 , C 28 , C 29 may be a heterocyclic group. have.
상기 아릴기, 플루오렌일기, 헤테로고리기, 지방족고리기, 방향족고리기, 알킬기, 알켄일기, 알킨일기, 알콕시기, 아릴옥시기, 아릴렌기, 플루오렌일렌기, 및 이웃한 기끼리 서로 결합하여 형성된 고리, R'과 R"이 서로 결합하여 형성된 고리, R1과 R2가 서로 결합하여 형성된 고리 중에서 적어도 하나가 플루오렌일기로 치환될 경우, 상기 플루오렌일기는 9,9-다이메틸-9H-플루오렌, 9,9-다이페닐-9H-플루오렌, 9,9'-스파이로바이플루오렌, 스파이로[벤조[b]플루오렌-11,9'-플루오렌], 벤조[b]플루오렌, 11,11-다이페닐-11H-벤조[b]플루오렌, 9-(나프탈렌-2-일)9-페닐-9H-플루오렌 등일 수 있다.The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups are bonded to each other When at least one of a ring formed by combining with each other, a ring formed by combining R′ and R″, and a ring formed by combining R 1 and R 2 with each other is substituted with a fluorenyl group, the fluorenyl group is 9,9-dimethyl -9H-fluorene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[ b ]fluorene-11,9'-fluorene], benzo[ b ]fluorene, 11,11-diphenyl- 11H -benzo[ b ]fluorene, 9-(naphthalen-2-yl)9-phenyl- 9H -fluorene, or the like.
상기 아릴기, 플루오렌일기, 헤테로고리기, 지방족고리기, 방향족고리기, 알킬기, 알켄일기, 알킨일기, 알콕시기, 아릴옥시기, 아릴렌기, 플루오렌일렌기, 및 이웃한 기끼리 서로 결합하여 형성된 고리, R'과 R"이 서로 결합하여 형성된 고리, R1과 R2가 서로 결합하여 형성된 고리 중에서 적어도 하나가 알킬기로 치환될 경우, 상기 알킬기는 예컨대, C1~C20, C1~C10, C1~C4, C1, C2, C3, C4 등의 알킬일기일 수 있다.The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups are bonded to each other When at least one of the ring formed by the above, the ring formed by bonding R′ and R″ to each other, and the ring formed by bonding R 1 and R 2 to each other is substituted with an alkyl group, the alkyl group is, for example, C 1 ~ C 20 , C 1 ~C 10 , C 1 ~C 4 , C 1 , C 2 , C 3 , may be an alkylyl group such as C 4 .
상기 아릴기, 플루오렌일기, 헤테로고리기, 지방족고리기, 방향족고리기, 알킬기, 알켄일기, 알킨일기, 알콕시기, 아릴옥시기, 아릴렌기, 플루오렌일렌기, 및 이웃한 기끼리 서로 결합하여 형성된 고리, R'과 R"이 서로 결합하여 형성된 고리, R1과 R2가 서로 결합하여 형성된 고리 중에서 적어도 하나가 알콕시기로 치환될 경우, 상기 알콕시기는 예컨대, C1~C20, C1~C10, C1~C4, C1, C2, C3, C4 등의 알콕시기일 수 있다.The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups are bonded to each other When at least one of a ring formed by combining with each other, a ring formed by combining R′ and R″, and a ring formed by combining R 1 and R 2 with each other is substituted with an alkoxy group, the alkoxy group is, for example, C 1 ~ C 20 , C 1 ~C 10 , C 1 ~C 4 , C 1 , C 2 , C 3 , may be an alkoxy group such as C 4 .
상기 아릴기, 플루오렌일기, 헤테로고리기, 지방족고리기, 방향족고리기, 알킬기, 알켄일기, 알킨일기, 알콕시기, 아릴옥시기, 아릴렌기, 플루오렌일렌기, 및 이웃한 기끼리 서로 결합하여 형성된 고리, R'과 R"이 서로 결합하여 형성된 고리, R1과 R2가 서로 결합하여 형성된 고리 중에서 적어도 하나가 지방족고리기로 치환될 경우, 상기 지방족고리기는 예컨대 C3~C30, C3~C29, C3~C28, C3~C27, C3~C26, C3~C25, C3~C24, C3~C23, C3~C22, C3~C21, C3~C20, C3~C19, C3~C18, C3~C17, C3~C16, C3~C15, C3~C14, C3~C13, C3~C12, C3~C11, C3~C10, C3~C8, C3~C6, C6, C10, C11, C12, C13, C14, C15, C16, C17, C18 등의 지방족고리기일 수 있다.The aryl group, fluorenyl group, heterocyclic group, aliphatic ring group, aromatic ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, arylene group, fluorenylene group, and neighboring groups are bonded to each other When at least one of the ring formed by the above, the ring formed by combining R′ and R″, and the ring formed by combining R 1 and R 2 with each other is substituted with an aliphatic ring group, the aliphatic ring group is, for example, C 3 ~ C 30 , C 3 ~C 29 , C 3 ~C 28 , C 3 ~C 27 , C 3 ~C 26 , C 3 ~C 25 , C 3 ~C 24 , C 3 ~C 23 , C 3 ~C 22 , C 3 ~ C 21 , C 3 ~C 20 , C 3 ~C 19 , C 3 ~C 18 , C 3 ~C 17 , C 3 ~C 16 , C 3 ~C 15 , C 3 ~C 14 , C 3 ~C 13 , C 3 ~C 12 , C 3 ~C 11 , C 3 ~C 10 , C 3 ~C 8 , C 3 ~C 6 , C 6 , C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , may be an aliphatic ring group such as C 18 .
상기 화학식 1은 하기 화학식 2 내지 화학식 22, 화학식 7-1 내지 화학식 10-1 중 하나로 표시될 수 있다.Chemical Formula 1 may be represented by one of Chemical Formulas 2 to 22, and Chemical Formulas 7-1 to 10-1.
<화학식 2> <화학식 3><Formula 2> <Formula 3>
Figure PCTKR2022003947-appb-I000010
Figure PCTKR2022003947-appb-I000010
<화학식 4><Formula 4>
Figure PCTKR2022003947-appb-I000011
Figure PCTKR2022003947-appb-I000011
<화학식 5> <화학식 6><Formula 5> <Formula 6>
Figure PCTKR2022003947-appb-I000012
Figure PCTKR2022003947-appb-I000012
<화학식 7> <화학식 8><Formula 7> <Formula 8>
Figure PCTKR2022003947-appb-I000013
Figure PCTKR2022003947-appb-I000013
<화학식 9> <화학식 10><Formula 9> <Formula 10>
Figure PCTKR2022003947-appb-I000014
Figure PCTKR2022003947-appb-I000014
<화학식 11> <화학식 12><Formula 11> <Formula 12>
Figure PCTKR2022003947-appb-I000015
Figure PCTKR2022003947-appb-I000015
<화학식 13> <화학식 14><Formula 13> <Formula 14>
Figure PCTKR2022003947-appb-I000016
Figure PCTKR2022003947-appb-I000016
<화학식 15> <화학식 16><Formula 15> <Formula 16>
Figure PCTKR2022003947-appb-I000017
Figure PCTKR2022003947-appb-I000017
<화학식 17> <화학식 18><Formula 17> <Formula 18>
Figure PCTKR2022003947-appb-I000018
Figure PCTKR2022003947-appb-I000018
<화학식 19> <화학식 20><Formula 19> <Formula 20>
Figure PCTKR2022003947-appb-I000019
Figure PCTKR2022003947-appb-I000019
<화학식 21> <화학식 22><Formula 21> <Formula 22>
Figure PCTKR2022003947-appb-I000020
Figure PCTKR2022003947-appb-I000020
<화학식 7-1> <화학식 8-1><Formula 7-1> <Formula 8-1>
Figure PCTKR2022003947-appb-I000021
Figure PCTKR2022003947-appb-I000021
<화학식 9-1> <화학식 10-1><Formula 9-1> <Formula 10-1>
Figure PCTKR2022003947-appb-I000022
Figure PCTKR2022003947-appb-I000022
상기 화학식 2 내지 화학식 22, 화학식 7-1 내지 화학식 10-1에서, 각 기호는 아래와 같이 정의될 수 있다.In Formulas 2 to 22, and Formulas 7-1 to 10-1, each symbol may be defined as follows.
R1~R4, R', R", Ar1, L, a, c, d는 화학식 1에서 정의된 것과 같고, *는 결합위치를 나타낸다. 예컨대, 화학식 12, 17 및 18에서, 아민그룹은 *로 표시된 탄소에 결합될 수 있고, 화학식 14, 21 및 22에서, 플루오렌 치환기가 *로 표시된 탄소에 결합될 수 있다.R 1 to R 4 , R', R", Ar 1 , L, a, c, and d are as defined in Formula 1, and * represents a bonding position. For example, in Formulas 12, 17 and 18, an amine group may be bonded to the carbon indicated by *, and in formulas 14, 21 and 22, a fluorene substituent may be bonded to the carbon indicated by *.
화학식 2 내지 화학식 6에서, b는 화학식 1에서 정의된 것과 같고, 화학식 7, 화학식 8, 화학식 11, 화학식 12, 화학식 15 내지 화학식 18, 화학식 7-1, 화학식 8-1에서, b는 0~3의 정수이고, 화학식 9, 화학식 10, 화학식 13, 화학식 14, 화학식 19 내지 화학식 22, 화학식 9-1 및 화학식 10-1에서, b는 0~4의 정수이며, b가 2 이상의 정수인 경우 R2 각각은 서로 같거나 상이하다.In Formulas 2 to 6, b is the same as defined in Formula 1, and in Formula 7, Formula 8, Formula 11, Formula 12, Formula 15 to Formula 18, Formula 7-1, and Formula 8-1, b is 0 to is an integer of 3, and in Formulas 9, 10, 13, 14, 19 to 22, Formulas 9-1 and 10-1, b is an integer of 0 to 4, and when b is an integer of 2 or more, R 2 Each is the same as or different from each other.
X는 직접결합, O, S, N(Ar1) 또는 C(R1)(R2)이다.X is a direct bond, O, S, N(Ar 1 ) or C(R 1 )(R 2 ).
R5, R6, R11 내지 R15, R1 및 R2는 서로 독립적으로 수소; 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; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C30의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C30의 헤테로고리기; C3-C30의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택되며, 이웃한 기끼리 서로 결합하여 고리를 형성할 수 있고, R1과 R2가 서로 결합하여 고리를 형성할 수 있다.R 5 , R 6 , R 11 to R 15 , R 1 and R 2 are each independently hydrogen; heavy hydrogen; halogen; a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Phosphine oxide unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; siloxane group; cyano group; nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 Alkoxy group; C 6 -C 20 aryloxy group; C 6 -C 20 An arylthio group; C 1 -C 20 Alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkynyl group; C 6 -C 30 Aryl group; fluorenyl group; C 2 -C 30 A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C 30 An aliphatic group; And it is selected from the group consisting of combinations thereof, adjacent groups may be bonded to each other to form a ring, and R 1 and R 2 may be bonded to each other to form a ring.
이웃한 기끼리, 예컨대 이웃한 R5끼리, 이웃한 R6끼리, 이웃한 R11끼리, 이웃한 R12끼리, 이웃한 R13끼리, 이웃한 R14끼리 또는 이웃한 R15끼리 서로 결합하여 고리를 형성할 경우, 상기 고리는 C6~C30의 방향족고리기; 플루오렌고리기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C30의 헤테로고리기; 및 C3~C30의 지방족고리기로 이루어진 군에서 선택될 수 있다.Neighboring groups, for example, neighboring R 5 , neighboring R 6 , neighboring R 11 , neighboring R 12 , neighboring R 13 , neighboring R 14 , or neighboring R 15 are bonded to each other. When forming a ring, the ring is a C 6 ~ C 30 aromatic ring group; fluorene ring group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 30 A heterocyclic group; And C 3 ~ C 30 It may be selected from the group consisting of an aliphatic cyclic group.
이웃한 기끼리 서로 결합하여 방향족고리를 형성할 경우, 상기 방향족고리는 예컨대, C6~C20, C6~C18, C6~C16, C6~C14, C6~C13, C6~C12, C6~C10, C6, C10, C12, C14, C15, C16, C18 등일 수 있고, 구체적으로, 벤젠, 나프탈렌, 안트라센, 페난트렌, 파이렌 등일 수 있다.When adjacent groups are bonded to each other to form an aromatic ring, the aromatic ring is, for example, C 6 ~ C 20 , C 6 ~ C 18 , C 6 ~ C 16 , C 6 ~ C 14 , C 6 ~ C 13 , C 6 ~ C 12 , C 6 ~ C 10 , C 6 , C 10 , C 12 , C 14 , C 15 , C 16 , C 18 , etc. may be, specifically, benzene, naphthalene, anthracene, phenanthrene, pyrene etc.
R1과 R2가 서로 결합하여 고리를 형성할 경우, 스파이로 화합물이 형성될 수 있다. R1과 R2가 서로 결합하여 고리를 형성할 경우, 상기 고리는 C6~C30의 방향족고리기; 플루오렌고리기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C30의 헤테로고리기; 및 C3~C30의 지방족고리기로 이루어진 군에서 선택될 수 있다.When R 1 and R 2 combine with each other to form a ring, a spiro compound may be formed. When R 1 and R 2 are bonded to each other to form a ring, the ring is a C 6 ~ C 30 aromatic ring group; fluorene ring group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 30 A heterocyclic group; And C 3 ~ C 30 It may be selected from the group consisting of an aliphatic cyclic group.
상기 Ar1은 C6~C30의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C30의 헤테로고리기; C3~C30의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택된다.The Ar 1 is a C 6 ~ C 30 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 30 A heterocyclic group; C 3 ~ C 30 of an aliphatic ring; and combinations thereof.
화학식 6, 화학식 7-1 내지 화학식 10-1에서, e는 0~5의 정수이고, 화학식 11 내지 화학식 22에서, e는 0~4의 정수이며, e가 2 이상의 정수인 경우 R5 각각은 서로 같거나 상이하다.In Formulas 6 and 7-1 to Formula 10-1, e is an integer of 0 to 5, in Formulas 11 to 22, e is an integer of 0 to 4, and when e is an integer of 2 or more, each of R 5 is each other same or different
f는 0~5의 정수이고, m, n, o 및 p는 각각 0~4의 정수이고, q는 0~3의 정수이며, 이들 각각이 2 이상의 정수인 경우 R6 각각, R11 각각, R12 각각, R13 각각, R14 각각, R15 각각은 서로 같거나 상이하다.f is an integer from 0 to 5, m, n, o and p are each an integer from 0 to 4, q is an integer from 0 to 3, and when each of these is an integer of 2 or more, each of R 6 , each of R 11 , R each of 12 , each of R 13 , each of R 14 and each of R 15 are the same as or different from each other.
화학식 2 내지 4, 화학식 7 내지 화학식 14, 화학식 7-1 내지 화학식 10-1에서 d가 0이거나 R4가 수소일 수 있다. 또한, 화학식 8에서, R1 내지 R6, R11 및 R12가 모두 수소이거나 a~f, m, n이 모두 0일 수 있다.In Formulas 2 to 4, Formulas 7 to 14, and Formulas 7-1 to 10-1, d may be 0 or R 4 may be hydrogen. In addition, in Formula 8, R 1 to R 6 , R 11 and R 12 may be all hydrogen, or a to f, m, and n may all be 0.
상기 R5, R6, R11 내지 R15, R1, R2, Ar1 중에서 적어도 하나가 아릴기인 경우, 상기 아릴기는 예컨대, C6~C30, C6~C29, C6~C28, C6~C27, C6~C26, C6~C25, C6~C24, C6~C23, C6~C22, C6~C21, C6~C20, C6~C19, C6~C18, C6~C17, C6~C16, C6~C15, C6~C14, C6~C13, C6~C12, C6~C11, C6~C10, C6, C10, C12, C13, C14, C15, C16, C17, C18 등의 아릴기일 수 있고, 구체적으로, 페닐, 바이페닐, 나프틸, 터페닐, 페난트렌, 트리페닐렌 등일 수 있다.When at least one of R 5 , R 6 , R 11 to R 15 , R 1 , R 2 , and Ar 1 is an aryl group, the aryl group is, for example, C 6 -C 30 , C 6 -C 29 , C 6 -C 28 , C 6 ~C 27 , C 6 ~C 26 , C 6 ~C 25 , C 6 ~C 24 , C 6 ~C 23 , C 6 ~C 22 , C 6 ~C 21 , C 6 ~C 20 , C 6 ~C 19 , C 6 ~C 18 , C 6 ~C 17 , C 6 ~C 16 , C 6 ~C 15 , C 6 ~C 14 , C 6 ~C 13 , C 6 ~C 12 , C 6 ~C 11 , C 6 ~C 10 , C 6 , C 10 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , may be an aryl group such as C 18 , specifically, phenyl, biphenyl , naphthyl, terphenyl, phenanthrene, triphenylene, and the like.
상기 R5, R6, R11 내지 R15, R1, R2, Ar1 중에서 적어도 하나가 헤테로고리기인 경우, 상기 헤테로고리는 예컨대, C2~C30, C2~C29, C2~C28, C2~C27, C2~C26, C2~C25, C2~C24, C2~C23, C2~C22, C2~C21, C2~C20, C2~C19, C2~C18, C2~C17, C2~C16, C2~C15, C2~C14, C2~C13, C2~C12, C2~C11, C2~C10, C2~C9, C2~C8, C2~C7, C2~C6, C2~C5, C2~C4, C2~C3, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29 등의 헤테로고리기일 수 있다.When at least one of R 5 , R 6 , R 11 to R 15 , R 1 , R 2 , and Ar 1 is a heterocyclic group, the heterocyclic group is, for example, C 2 to C 30 , C 2 to C 29 , C 2 ~C 28 , C 2 ~C 27 , C 2 ~C 26 , C 2 ~C 25 , C 2 ~C 24 , C 2 ~C 23 , C 2 ~C 22 , C 2 ~C 21 , C 2 ~C 20 , C 2 ~C 19 , C 2 ~C 18 , C 2 ~C 17 , C 2 ~C 16 , C 2 ~C 15 , C 2 ~C 14 , C 2 ~C 13 , C 2 ~C 12 , C 2 ~C 11 , C 2 ~C 10 , C 2 ~C 9 , C 2 ~C 8 , C 2 ~C 7 , C 2 ~C 6 , C 2 ~C 5 , C 2 ~C 4 , C 2 ~C 3 , C 2 , C 3 , C 4 , C 5 , C 6 , C 7 , C 8 , C 9 , C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , C 18 , C 19 , C 20 , C 21 , C 22 , C 23 , C 24 , C 25 , C 26 , C 27 , C 28 , C 29 may be a heterocyclic group.
상기 R5, R6, R11 내지 R15, R1, R2, Ar1 중에서 적어도 하나가 플루오렌일기인 경우, 상기 플루오렌일기 또는 플루오렌일렌기는 9,9-다이메틸-9H-플루오렌, 9,9-다이페닐-9H-플루오렌, 9,9'-스파이로바이플루오렌, 스파이로[벤조[b]플루오렌-11,9'-플루오렌], 벤조[b]플루오렌, 11,11-다이페닐-11H-벤조[b]플루오렌, 9-(나프탈렌-2-일)9-페닐-9H-플루오렌 등일 수 있다.When at least one of R 5 , R 6 , R 11 to R 15 , R 1 , R 2 , and Ar 1 is a fluorenyl group, the fluorenyl group or the fluorenylene group is 9,9-dimethyl-9H-flu Orene, 9,9-diphenyl-9H-fluorene, 9,9'-spirobifluorene, spiro[benzo[ b ]fluorene-11,9'-fluorene], benzo[ b ]fluorene , 11,11-diphenyl- 11H -benzo[ b ]fluorene, 9-(naphthalen-2-yl)9-phenyl- 9H -fluorene, and the like.
상기 R5, R6, R11 내지 R15, R1, R2, Ar1 중에서 적어도 적어도 하나가 지방족고리기인 경우, 상기 지방족고리기는 예컨대, C3~C30, C3~C29, C3~C28, C3~C27, C3~C26, C3~C25, C3~C24, C3~C23, C3~C22, C3~C21, C3~C20, C3~C19, C3~C18, C3~C17, C3~C16, C3~C15, C3~C14, C3~C13, C3~C12, C3~C11, C3~C10, C3~C8, C3~C6, C6, C10, C11, C12, C13, C14, C15, C16, C17, C18 등의 지방족고리기일 수 있고, 구체적으로, 사이클로헥산일기, 아다만틸기 등일 수 있다.When at least one of R 5 , R 6 , R 11 to R 15 , R 1 , R 2 , and Ar 1 is an aliphatic cyclic group, the aliphatic cyclic group is, for example, C 3 to C 30 , C 3 to C 29 , C 3 ~C 28 , C 3 ~C 27 , C 3 ~C 26 , C 3 ~C 25 , C 3 ~C 24 , C 3 ~C 23 , C 3 ~C 22 , C 3 ~C 21 , C 3 ~ C 20 , C 3 ~C 19 , C 3 ~C 18 , C 3 ~C 17 , C 3 ~C 16 , C 3 ~C 15 , C 3 ~C 14 , C 3 ~C 13 , C 3 ~C 12 , C 3 ~C 11 , C 3 ~C 10 , C 3 ~C 8 , C 3 ~C 6 , C 6 , C 10 , C 11 , C 12 , C 13 , C 14 , C 15 , C 16 , C 17 , may be an aliphatic ring group such as C 18 , and specifically, may be a cyclohexanyl group, an adamantyl group, or the like.
상기 R5, R6, R11 내지 R15, R1, R2 중에서 적어도 하나가 알킬기인 경우, 상기 알킬기는 예컨대, C1~C20, C1~C10, C1~C4, C1, C2, C3, C4 등의 알킬일기일 수 있고, 예컨대, 메틸기, 에틸기, t-부틸기 등일 수 있다.When at least one of R 5 , R 6 , R 11 to R 15 , R 1 , and R 2 is an alkyl group, the alkyl group is, for example, C 1 to C 20 , C 1 to C 10 , C 1 to C 4 , C 1 , C 2 , C 3 , may be an alkylyl group such as C 4 , for example, a methyl group, an ethyl group, a t-butyl group, or the like.
상기 R5, R6, R11 내지 R15, R1, R2, Ar1, 이웃한 기끼리 서로 결합하여 형성된 고리, R1과 R2는 서로 결합하여 형성된 고리 각각은 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; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C30의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C30의 헤테로고리기; 및 C3-C30의 지방족고리기로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있다.The R 5 , R 6 , R 11 To R 15 , R 1 , R 2 , Ar 1 , a ring formed by bonding adjacent groups to each other, R 1 and R 2 A ring formed by bonding to each other is 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; cyano group; nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 alkoxy group; C 6 -C 20 aryloxy group; C 6 -C 20 Arylthio group; C 1 -C 20 Alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkynyl group; C 6 -C 30 Aryl group; fluorenyl group; C 2 -C 30 A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; And C 3 -C 30 It may be substituted with one or more substituents selected from the group consisting of an aliphatic ring group.
구체적으로, 상기 화학식 1로 표시되는 화합물은 하기 화합물 중 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 PCTKR2022003947-appb-I000023
Figure PCTKR2022003947-appb-I000023
Figure PCTKR2022003947-appb-I000024
Figure PCTKR2022003947-appb-I000024
Figure PCTKR2022003947-appb-I000025
Figure PCTKR2022003947-appb-I000025
Figure PCTKR2022003947-appb-I000026
Figure PCTKR2022003947-appb-I000026
Figure PCTKR2022003947-appb-I000027
Figure PCTKR2022003947-appb-I000027
Figure PCTKR2022003947-appb-I000028
Figure PCTKR2022003947-appb-I000028
Figure PCTKR2022003947-appb-I000029
Figure PCTKR2022003947-appb-I000029
Figure PCTKR2022003947-appb-I000030
Figure PCTKR2022003947-appb-I000030
Figure PCTKR2022003947-appb-I000031
.
Figure PCTKR2022003947-appb-I000031
.
다른 측면에서, 본 발명은 제 1전극; 제 2전극; 상기 제 1전극과 상기 제 2전극 사이에 형성된 유기물층을 포함하는 유기전기소자를 제공하며, 상기 유기물층은 화학식 1로 표시되는 화합물을 포함한다.In another aspect, the present invention provides a first electrode; a second electrode; It provides an organic electric device including an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer includes a compound represented by Chemical Formula 1.
상기 유기물층은 발광층, 상기 발광층과 제 1전극 사이에 형성된 정공수송층 및 상기 정공수송층과 상기 제 1전극 사이에 형성된 발광보조층을 포함하며, 상기 화합물은 상기 정공수송층 및 발광보조층 중 적어도 하나의 층에 포함될 수 있다.The organic material layer includes a light emitting layer, a hole transport layer formed between the light emitting layer and the first electrode, and a light emitting auxiliary layer formed between the hole transport layer and the first electrode, wherein the compound is at least one of the hole transport layer and the light emission auxiliary layer. can be included in
상기 유기전기소자는 화학식 1로 표시되는 화합물을 포함하는 광효율개선층을 더 포함할 수 있으며, 이때 광효율개선층은 상기 제 1전극 또는 제 2전극의 양면 중에서 상기 유기물층과 접하지 않는 층에 형성된다.The organic electric device may further include a light efficiency improving layer containing the compound represented by Formula 1, wherein the light efficiency improving layer is formed on a layer that does not come into contact with the organic material layer among both surfaces of the first electrode or the second electrode. .
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, a light emitting layer, and an electron transport layer sequentially formed on the anode, and may further include a charge generating layer formed between the two or more stacks.
또 다른 측면에서, 본 발명은 상기 화학식 1로 표시되는 유기전기소자를 포함하는 디스플레이장치와, 상기 디스플레이장치를 구동하는 제어부를 포함하는 전자장치를 제공한다.In another aspect, the present invention provides an electronic device including a display device including the organic electric device represented by Chemical Formula 1, and a controller for driving the display device.
이하, 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 of the synthesis of the compound represented by Chemical Formula 1 and the preparation of an organic electric device according to the present invention will be described in detail with reference to examples, but the present invention is not limited to the following examples.
[합성예][Synthesis Example]
본 발명에 따른 화학식 1로 표시되는 화합물은 하기 반응식 1과 같이 Sub 1과 Sub 2를 반응시켜 합성될 수 있으나, 이에 한정되는 것은 아니다.The compound 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> (Hal은 I, Br 또는 Cl임)<Scheme 1> (Hal is I, Br or Cl)
Figure PCTKR2022003947-appb-I000032
Figure PCTKR2022003947-appb-I000032
Sub 1의 예시Sub 1 example
상기 반응식 1의 Sub 1은 아래와 같은 화합물일 수 있으나, 이에 한정되는 것은 아니며, 하기 화합물의 FD-MS(Field Desorption-Mass Spectrometry) 값은 표 1과 같다.Sub 1 of Scheme 1 may be the following compound, but is not limited thereto, and FD-MS (Field Desorption-Mass Spectrometry) values of the following compound are shown in Table 1.
Figure PCTKR2022003947-appb-I000033
Figure PCTKR2022003947-appb-I000033
Figure PCTKR2022003947-appb-I000034
Figure PCTKR2022003947-appb-I000034
[표 1][Table 1]
Figure PCTKR2022003947-appb-I000035
Figure PCTKR2022003947-appb-I000035
Sub 2의 합성예Synthesis example of Sub 2
반응식 1의 Sub 2는 하기 반응식 2와 같은 반응경로에 의해 합성될 수 있으며, 하기 Sub 2-I는 하기 반응식 3에 의해 합성될 수 있으나, 이에 한정되는 것은 아니다.Sub 2 of Scheme 1 may be synthesized by the reaction route as shown in Scheme 2 below, and Sub 2-I may be synthesized by Scheme 3 below, but is not limited thereto.
<반응식 2><Scheme 2>
Figure PCTKR2022003947-appb-I000036
Figure PCTKR2022003947-appb-I000036
<반응식 3><Scheme 3>
Figure PCTKR2022003947-appb-I000037
Figure PCTKR2022003947-appb-I000037
1. Sub 2-3 합성예1. Sub 2-3 Synthesis Example
Figure PCTKR2022003947-appb-I000038
Figure PCTKR2022003947-appb-I000038
(1) Sub 2-3-c 합성예(1) Sub 2-3-c synthesis example
Sub 2-3-a (26g, 91.9 mmol)에 Sub 2-3-b (22.8g, 91.9 mmol), Pd(PPh3)4 (0.05 당량), K2CO3 (3 당량), THF/H2O (306 ml/153 ml)을 넣고, 12시간 환류시킨다. 반응이 종료되면 반응물의 온도를 상온으로 식히고, THF를 제거한다. MC로 추출하고 물로 닦아주었다. 유기층을 MgSO4로 건조하고 농축한 후 생성된 농축물을 실리카겔 칼럼으로 분리하여 생성물 28.5 g 을 얻었다. (수율: 96.4 %)Sub 2-3-a (26g, 91.9 mmol) to Sub 2-3-b (22.8g, 91.9 mmol), Pd(PPh 3 ) 4 (0.05 equiv), K 2 CO 3 (3 equiv), THF/H 2 O (306 ml/153 ml) was added and refluxed for 12 hours. When the reaction is completed, the temperature of the reactant is cooled to room temperature, and THF is removed. It was extracted with MC and washed with water. The organic layer was dried over MgSO 4 and concentrated, and the resulting concentrate was separated by a silica gel column to obtain 28.5 g of a product. (Yield: 96.4%)
(2) Sub 2-I-3 합성예(2) Sub 2-I-3 Synthesis Example
Sub 2-3-c (28.5g, 79.3 mmol)에 Sub 2-3-d(12.4g, 79.3 mmol), Pd(PPh3)4 (0.05 당량), K2CO3 (3 당량), THF/H2O (264 ml/132 ml)을 넣고 상기 Sub 2-3-c 합성예와 같은 방법으로 진행하여 생성물 25.8 g 을 얻었다. (수율: 83.4 %)Sub 2-3-c (28.5 g, 79.3 mmol) to Sub 2-3-d (12.4 g, 79.3 mmol), Pd(PPh 3 ) 4 (0.05 equiv), K 2 CO 3 (3 equiv), THF/ H 2 O (264 ml/132 ml) was added, followed by the same method as in the Synthesis Example of Sub 2-3-c to obtain 25.8 g of a product. (Yield: 83.4%)
(3) Sub 2-3 합성예(3) Sub 2-3 Synthesis Example
Sub 2-I-3 (25.8 g, 66 mmol)을 toluene (676 ml)에 녹인 후, Sub 2-II-3 (11.7 g, 69.3 mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량)을 첨가하고 100℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 28.4 g을 얻었다. (수율: 82.3 %)After dissolving Sub 2-I-3 (25.8 g, 66 mmol) in toluene (676 ml), Sub 2-II-3 (11.7 g, 69.3 mmol), Pd 2 (dba) 3 (0.03 equiv), P ( t-Bu) 3 (0.06 equiv), NaOt-Bu (3 equiv) were added and stirred at 100°C. Upon completion of the reaction, 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 28.4 g of a product. (Yield: 82.3%)
2. Sub 2-8 합성예2. Sub 2-8 Synthesis Example
Figure PCTKR2022003947-appb-I000039
Figure PCTKR2022003947-appb-I000039
Sub 2-I-8(25g, 79.4mmol)에 Sub 2-II-8 (18.8g, 83.38mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (814ml)을 첨가하고, 상기 Sub 2-3 합성예와 같은 방법으로 진행하여 생성물 32.2g (수율: 80.7%)를 얻었다.Sub 2-I-8 (25 g, 79.4 mmol) to Sub 2-II-8 (18.8 g, 83.38 mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv), NaO t -Bu (3 equivalents) and Toluene (814ml) were added, and the same method as in Sub 2-3 Synthesis Example was followed to obtain 32.2 g of a product (yield: 80.7%).
3. Sub 2-14 합성예3. Sub 2-14 Synthesis Example
Figure PCTKR2022003947-appb-I000040
Figure PCTKR2022003947-appb-I000040
Sub 2-I-14(22g, 69.9mmol)에 Sub 2-II-14 (15.4g, 73.4mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (716ml)을 첨가하고, 상기 Sub 2-3 합성예와 같은 방법으로 진행하여 생성물 27.6g (수율: 81%)를 얻었다.Sub 2-I-14 (22 g, 69.9 mmol) to Sub 2-II-14 (15.4 g, 73.4 mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv), NaO t -Bu (3 equivalents) and Toluene (716ml) were added, and the same method as in Sub 2-3 Synthesis Example was followed to obtain 27.6 g (yield: 81%) of the product.
4. Sub 2-27 합성예4. Sub 2-27 Synthesis Example
Figure PCTKR2022003947-appb-I000041
Figure PCTKR2022003947-appb-I000041
Sub 2-I-27 (23 g, 58.8 mmol)에 Sub 2-II-27 (12.9 g, 61.8 mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (603ml)을 첨가하고, 상기 Sub 2-3 합성예와 같은 방법으로 진행하여 생성물 26.7 g (수율: 80.5%)를 얻었다.Sub 2-I-27 (23 g, 58.8 mmol) to Sub 2-II-27 (12.9 g, 61.8 mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv) , NaO t -Bu (3 equivalents), and Toluene (603ml) were added, and the same method as in Sub 2-3 Synthesis Example was followed to obtain 26.7 g of a product (yield: 80.5%).
5. Sub 2-32 합성예5. Sub 2-32 Synthesis Example
Figure PCTKR2022003947-appb-I000042
Figure PCTKR2022003947-appb-I000042
Sub 2-I-32 (19 g, 47.9 mmol)에 Sub 2-II-32 (8.5 g, 50.3 mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (491ml)을 첨가하고, 상기 Sub 2-3 합성예와 같은 방법으로 진행하여 생성물 19.2 g (수율: 75.6%)를 얻었다.Sub 2-I-32 (19 g, 47.9 mmol) to Sub 2-II-32 (8.5 g, 50.3 mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv) , NaO t -Bu (3 equivalents) and Toluene (491ml) were added, and the same method as in Sub 2-3 Synthesis Example was followed to obtain 19.2 g of a product (yield: 75.6%).
6. Sub 2-39 합성예6. Sub 2-39 Synthesis Example
Figure PCTKR2022003947-appb-I000043
Figure PCTKR2022003947-appb-I000043
Sub 2-I-39 (20 g, 51.2 mmol)에 Sub 2-II-39 (15.3 g, 53.7 mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3(0.06 당량), NaOt-Bu (3 당량), Toluene (524ml)을 첨가하고, 상기 Sub 2-3 합성예와 같은 방법으로 진행하여 생성물 23.2 g (수율: 71%)를 얻었다.Sub 2-I-39 (20 g, 51.2 mmol) to Sub 2-II-39 (15.3 g, 53.7 mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv) , NaO t -Bu (3 equivalents) and Toluene (524ml) were added, and the same method as in Sub 2-3 Synthesis Example was followed to obtain 23.2 g of a product (yield: 71%).
7. Sub 2-53 합성예7. Sub 2-53 Synthesis Example
Figure PCTKR2022003947-appb-I000044
Figure PCTKR2022003947-appb-I000044
Sub 2-I-53 (21 g, 66.7 mmol)에 Sub 2-II-53 (12.8 g, 70 mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (684ml)을 첨가하고, 상기 Sub 2-3 합성예와 같은 방법으로 진행하여 생성물 23.5g (수율: 76.2%)를 얻었다.Sub 2-I-53 (21 g, 66.7 mmol) to Sub 2-II-53 (12.8 g, 70 mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv) , NaO t -Bu (3 equivalents) and Toluene (684ml) were added, and the same method as in Sub 2-3 Synthesis Example was followed to obtain 23.5 g of a product (yield: 76.2%).
8. Sub 2-66 합성예8. Sub 2-66 Synthesis Example
Figure PCTKR2022003947-appb-I000045
Figure PCTKR2022003947-appb-I000045
Sub 2-I-66 (22 g, 56.3 mmol)에 Sub 2-II-66 (12.9 g, 59.1 mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (577ml)을 첨가하고, 상기 Sub 2-3 합성예와 같은 방법으로 진행하여 생성물 26.1 g (수율: 80.9%)를 얻었다.Sub 2-I-66 (22 g, 56.3 mmol) to Sub 2-II-66 (12.9 g, 59.1 mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv) , NaO t -Bu (3 equivalents) and Toluene (577ml) were added, and the same method as in Sub 2-3 Synthesis Example was followed to obtain 26.1 g of a product (yield: 80.9%).
9. Sub 2-68 합성예9. Sub 2-68 Synthesis Example
Figure PCTKR2022003947-appb-I000046
Figure PCTKR2022003947-appb-I000046
Sub 2-I-68 (19 g, 63.4 mmol)에 Sub 2-II-68 (11 g, 63.4 mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (619ml)을 첨가하고, 상기 Sub 2-3 합성예와 같은 방법으로 진행하여 생성물 21 g (수율: 76.8%)를 얻었다.Sub 2-I-68 (19 g, 63.4 mmol) to Sub 2-II-68 (11 g, 63.4 mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv) , NaO t -Bu (3 equivalents) and Toluene (619ml) were added, and the same method as in Sub 2-3 Synthesis Example was followed to obtain 21 g of a product (yield: 76.8%).
10. Sub 2-71 합성예10. Sub 2-71 Synthesis Example
Figure PCTKR2022003947-appb-I000047
Figure PCTKR2022003947-appb-I000047
Sub 2-I-71 (19 g, 43.5 mmol)에 Sub 2-II-71 (8.5 g, 45.7 mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (446ml)을 첨가하고, 상기 Sub 2-3 합성예와 같은 방법으로 진행하여 생성물 16.4 g (수율: 69.8%)를 얻었다.Sub 2-I-71 (19 g, 43.5 mmol) to Sub 2-II-71 (8.5 g, 45.7 mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv) , NaO t -Bu (3 equivalents), and Toluene (446ml) were added, and the same method as in Sub 2-3 Synthesis Example was followed to obtain 16.4 g of a product (yield: 69.8%).
Sub 2에 속하는 화합물은 아래와 같은 화합물일 수 있으나 이에 한정되는 것은 아니며, 표 2는 하기 화합물의 FD-MS 값을 나타낸다.The compound belonging to Sub 2 may be a compound as follows, but is not limited thereto, and Table 2 shows FD-MS values of the following compounds.
Figure PCTKR2022003947-appb-I000048
Figure PCTKR2022003947-appb-I000048
Figure PCTKR2022003947-appb-I000049
Figure PCTKR2022003947-appb-I000049
Figure PCTKR2022003947-appb-I000050
Figure PCTKR2022003947-appb-I000050
Figure PCTKR2022003947-appb-I000051
Figure PCTKR2022003947-appb-I000051
[표 2][Table 2]
Figure PCTKR2022003947-appb-I000052
Figure PCTKR2022003947-appb-I000052
Figure PCTKR2022003947-appb-I000053
Figure PCTKR2022003947-appb-I000053
최종 화합물의 합성예Synthesis example of final compound
1. P1-1 합성예1. P1-1 Synthesis Example
Figure PCTKR2022003947-appb-I000054
Figure PCTKR2022003947-appb-I000054
Sub 1-2 (32g, 91.52 mmol)을 toluene (938 ml)에 녹인 후, Sub 2-48 (43.01 g, 96.09 mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량) 을 첨가하고 100℃에서 교반하였다. 반응이 완료되면 CH2Cl2와 물로 추출한 후 유기층을 MgSO4로 건조하고 농축하였다. 이후, 농축물을 실리카겔 칼럼으로 분리 후 재결정하여 생성물 44.27g을 얻었다. (수율: 75.6%)After dissolving Sub 1-2 (32 g, 91.52 mmol) in toluene (938 ml), Sub 2-48 (43.01 g, 96.09 mmol), Pd 2 (dba) 3 (0.03 equiv), P(t-Bu) 3 (0.06 equiv), NaOt-Bu (3 equiv) was added and stirred at 100°C. Upon completion of the reaction, the mixture was extracted with CH 2 Cl 2 and water, and the organic layer was dried over MgSO 4 and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 44.27 g of a product. (Yield: 75.6%)
2. P1-3 합성예 2. P1-3 Synthesis Example
Figure PCTKR2022003947-appb-I000055
Figure PCTKR2022003947-appb-I000055
Sub 1-2(30g, 109.82mmol)에 Sub 2-3 (60.39g, 115.31mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (1126ml)을 첨가하고, 상기 P1-1의 합성예와 같이 진행하여 생성물 67.8g (수율: 86.2%)를 얻었다.Sub 1-2 (30 g, 109.82 mmol) to Sub 2-3 (60.39 g, 115.31 mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv), NaO t -Bu (3 equivalents) and Toluene (1126ml) were added, and the same procedure was followed in the same manner as in the synthesis example of P1-1 to obtain 67.8 g (yield: 86.2%) of a product.
3. P1-8 합성예 3. P1-8 Synthesis Example
Figure PCTKR2022003947-appb-I000056
Figure PCTKR2022003947-appb-I000056
Sub 1-2 (28g, 102.5mmol)에 Sub 2-5 (48.2g, 107.63mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (1051ml)을 첨가하고, 상기 P1-1의 합성예와 같이 진행하여 생성물 54.1g (수율: 82.4%)를 얻었다.Sub 1-2 (28 g, 102.5 mmol) to Sub 2-5 (48.2 g, 107.63 mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv), NaO t -Bu (3 equivalents) and Toluene (1051 ml) were added, and the same procedure as in the synthesis example of P1-1 was followed to obtain 54.1 g of a product (yield: 82.4%).
4. P1-13 합성예 4. Synthesis example of P1-13
Figure PCTKR2022003947-appb-I000057
Figure PCTKR2022003947-appb-I000057
Sub 1-5(31g, 88.7mmol)에 Sub 2-13 (41.7g, 93.2mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (910ml)을 첨가하고, 상기 P1-1의 합성예와 같이 진행하여 생성물 48.4g (수율: 76.1%)를 얻었다.Sub 1-5 (31 g, 88.7 mmol) to Sub 2-13 (41.7 g, 93.2 mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv), NaO t -Bu (3 equivalents) and Toluene (910 ml) were added, and the same procedure was followed in the same manner as in the synthesis example of P1-1 to obtain 48.4 g (yield: 76.1%) of a product.
5. P1-19 합성예 5. P1-19 Synthesis Example
Figure PCTKR2022003947-appb-I000058
Figure PCTKR2022003947-appb-I000058
Sub 1-2(24g, 87.9mmol)에 Sub 2-18 (45.9g, 92.3mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (901ml)을 첨가하고, 상기 P1-1의 합성예와 같이 진행하여 생성물 43.9g (수율: 72.4%)를 얻었다.Sub 1-2 (24 g, 87.9 mmol) to Sub 2-18 (45.9 g, 92.3 mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv), NaO t -Bu (3 equivalents) and Toluene (901 ml) were added, and the same procedure was followed in the same manner as in the synthesis example of P1-1 to obtain 43.9 g of a product (yield: 72.4%).
6. P1-38 합성예6. P1-38 Synthesis Example
Figure PCTKR2022003947-appb-I000059
Figure PCTKR2022003947-appb-I000059
Sub 1-2(22g, 80.5mmol)에 Sub 2-64(44.3g, 84.6mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (825ml)을 첨가하고, 상기 P1-1의 합성예와 같이 진행하여 생성물 48.2g (수율: 83.6%)를 얻었다.Sub 1-2 (22 g, 80.5 mmol) to Sub 2-64 (44.3 g, 84.6 mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv), NaO t -Bu (3 equivalents) and Toluene (825 ml) were added, and the same procedure was followed in the same manner as in the synthesis example of P1-1 to obtain 48.2 g (yield: 83.6%) of a product.
7. P2-9 합성예7. P2-9 Synthesis Example
Figure PCTKR2022003947-appb-I000060
Figure PCTKR2022003947-appb-I000060
Sub 1-10(20g, 50.6mmol)에 Sub 2-56 (28.6g, 53.1mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (519ml)을 첨가하고, 상기 P1-1의 합성예와 같이 진행하여 생성물 30.7g (수율: 71.3%)를 얻었다.Sub 1-10 (20g, 50.6mmol) to Sub 2-56 (28.6g, 53.1mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv), NaO t -Bu (3 equivalents) and Toluene (519ml) were added, and the same procedure was followed in the same manner as in the synthesis example of P1-1 to obtain 30.7 g (yield: 71.3%) of a product.
8. P2-20 합성예8. P2-20 Synthesis Example
Figure PCTKR2022003947-appb-I000061
Figure PCTKR2022003947-appb-I000061
Sub 1-14(21g, 46.5mmol)에 Sub 2-66 (28g, 48.8mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (477ml)을 첨가하고, 상기 P1-1의 합성예와 같이 진행하여 생성물 30.2g (수율: 68.7%)를 얻었다.Sub 1-14 (21 g, 46.5 mmol) to Sub 2-66 (28 g, 48.8 mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv), NaO t -Bu ( 3 equivalents), Toluene (477ml) was added, and the same procedure as in the synthesis example of P1-1 was carried out to obtain 30.2g (yield: 68.7%) of a product.
9. P3-8 합성예9. P3-8 Synthesis Example
Figure PCTKR2022003947-appb-I000062
Figure PCTKR2022003947-appb-I000062
Sub 1-15(19g, 47.82mmol)에 Sub 2-20 (28.3g, 50.2mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (490ml)을 첨가하고, 상기 P1-1의 합성예와 같이 진행하여 생성물 27.5g (수율: 65.3%)를 얻었다.Sub 1-15 (19g, 47.82mmol) to Sub 2-20 (28.3g, 50.2mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv), NaO t -Bu (3 equivalents) and Toluene (490ml) were added, and the same procedure was followed in the same manner as in the synthesis example of P1-1 to obtain 27.5 g of a product (yield: 65.3%).
10. P3-26 합성예10. Synthesis example of P3-26
Figure PCTKR2022003947-appb-I000063
Figure PCTKR2022003947-appb-I000063
Sub 1-22(18g, 53.7 mmol)에 Sub 2-26 (30.3g, 56.4mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (550ml)을 첨가하고, 상기 P1-1의 합성예와 같이 진행하여 생성물 31.5g (수율: 74.1%)를 얻었다.Sub 1-22 (18 g, 53.7 mmol) to Sub 2-26 (30.3 g, 56.4 mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv), NaO t -Bu (3 equivalents) and Toluene (550 ml) were added, and the same procedure was followed in the same manner as in the synthesis example of P1-1 to obtain 31.5 g (yield: 74.1%) of a product.
11. P4-3 합성예11. P4-3 Synthesis Example
Figure PCTKR2022003947-appb-I000064
Figure PCTKR2022003947-appb-I000064
Sub 1-25(20g, 50.3mmol)에 Sub 2-51 (29.8g, 52.8mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (516ml)을 첨가하고, 상기 P1-1의 합성예와 같이 진행하여 생성물 33.8g (수율: 76.4%)를 얻었다.Sub 1-25 (20 g, 50.3 mmol) to Sub 2-51 (29.8 g, 52.8 mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv), NaO t -Bu (3 equivalents) and Toluene (516ml) were added, and the same procedure was followed in the same manner as in the synthesis example of P1-1 to obtain 33.8 g (yield: 76.4%) of a product.
12. P5-1 합성예12. P5-1 Synthesis Example
Figure PCTKR2022003947-appb-I000065
Figure PCTKR2022003947-appb-I000065
Sub 1-28(31g, 74.4 mmol)에 Sub 2-3 (41.4g, 79.1mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (773ml)을 첨가하고, 상기 P1-1의 합성예와 같이 진행하여 생성물 53.5g (수율: 83.1%)를 얻었다.Sub 1-28 (31 g, 74.4 mmol) to Sub 2-3 (41.4 g, 79.1 mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv), NaO t -Bu (3 equivalents) and Toluene (773 ml) were added, and the same procedure as in the synthesis example of P1-1 was carried out to obtain 53.5 g of a product (yield: 83.1%).
13. P5-16 합성예13. P5-16 Synthesis Example
Figure PCTKR2022003947-appb-I000066
Figure PCTKR2022003947-appb-I000066
Sub 1-29 (25g, 60.8mmol)에 Sub 2-73 (33.4g, 63.8mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (623ml)을 첨가하고, 상기 P1-1의 합성예와 같이 진행하여 생성물 35.9g (수율: 69.1%)를 얻었다.Sub 1-29 (25 g, 60.8 mmol) to Sub 2-73 (33.4 g, 63.8 mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv), NaO t -Bu (3 equivalents) and Toluene (623 ml) were added, and the same procedure was followed in the same manner as in the synthesis example of P1-1 to obtain 35.9 g (yield: 69.1%) of a product.
14. P5-19 합성예14. Synthesis example of P5-19
Figure PCTKR2022003947-appb-I000067
Figure PCTKR2022003947-appb-I000067
Sub 1-30(19g, 44.5 mmol)에 Sub 2-76 (29.9g, 46.7mmol), Pd2(dba)3 (0.03 당량), P(t-Bu)3 (0.06 당량), NaOt-Bu (3 당량), Toluene (456ml)을 첨가하고, 상기 P1-1의 합성예와 같이 진행하여 생성물 27g (수율: 61.6%)를 얻었다.Sub 1-30 (19g, 44.5 mmol) to Sub 2-76 (29.9g, 46.7mmol), Pd 2 (dba) 3 (0.03 equiv), P( t -Bu) 3 (0.06 equiv), NaO t -Bu (3 equivalents) and Toluene (456 ml) were added, and the same procedure was followed in the same manner as in the synthesis example of P1-1 to obtain 27 g of a product (yield: 61.6%).
상기와 같은 합성예에 따라 제조된 본 발명의 화합물의 FD-MS 값은 하기 표 3과 같다.FD-MS values of the compounds of the present invention prepared according to the above synthesis examples are shown in Table 3 below.
[표 3][Table 3]
Figure PCTKR2022003947-appb-I000068
Figure PCTKR2022003947-appb-I000068
Figure PCTKR2022003947-appb-I000069
Figure PCTKR2022003947-appb-I000069
Figure PCTKR2022003947-appb-I000070
Figure PCTKR2022003947-appb-I000070
유기전기소자의 제조 및 평가Manufacturing and evaluation of organic electric devices
[실시예 1] 녹색유기전기발광소자 (정공수송층)[Example 1] Green organic electroluminescent device (hole transport layer)
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-TNATA로 약기함)을 60nm 두께로 진공증착하여 정공주입층을 형성한 후, 상기 정공주입층 상에 본 발명의 화합물 P1-1을 60 nm 두께로 진공증착하여 정공수송층을 형성하였다.N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4 on the ITO layer (anode) formed on the glass substrate -diamine (hereinafter abbreviated as 2-TNATA) was vacuum-deposited to a thickness of 60 nm to form a hole injection layer, and then the compound P1-1 of the present invention was vacuum-deposited to a thickness of 60 nm on the hole injection layer to form a hole transport layer was formed.
상기 정공수송층 상에 호스트로 4,4'-N,N'-dicarbazole-biphenyl (이하, CBP로 약기함)을, 도펀트로 tris(2-phenylpyridine)-iridium (이하, "Ir(ppy)3라 함)을 90:10 중량비로 사용하여 30 nm 두께의 발광층을 형성하였다.4,4'-N,N'-dicarbazole-biphenyl (hereinafter abbreviated as CBP) as a host on the hole transport layer and tris(2-phenylpyridine)-iridium (hereinafter, "Ir(ppy) 3 la" as a dopant ) was used in a weight ratio of 90:10 to form a light emitting layer having a thickness of 30 nm.
이어서, 상기 발광층 상에 (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (이하, BAlq로 약기함)를 5 nm 두께로 증착하여 정공저지층을 형성하고, 상기 정공저지층 상에 트리스(8-퀴놀리놀)알루미늄(이하 Alq3로 약칭함)을 40 nm 두께로 증착하여 전자수송층을 형성하였다. Then, (1,1'-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter abbreviated as BAlq) was deposited on the light emitting layer to a thickness of 5 nm to form a hole blocking layer, , tris (8-quinolinol) aluminum (hereinafter abbreviated as 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 on the electron transport layer to a thickness of 0.2 nm 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.
[실시예 2] 내지 [실시예 27] [Example 2] to [Example 27]
정공수송층 물질로 본 발명의 화합물 P1-1 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 P1-1 of the present invention as the hole transport layer material.
[비교예 1][Comparative Example 1]
정공수송층 물질로 N,N'-bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (이하 NPB로 약기함)를 사용한 것을 제외하고는 상기 실시예 1과 동일한 방법으로 유기전기발광소자를 제작하였다.N,N'-bis(1-naphthalenyl)-N,N'-bis-phenyl-(1,1'-biphenyl)-4,4'-diamine (hereinafter abbreviated as NPB) was used as the hole transport layer material. An organic electroluminescent device was manufactured in the same manner as in Example 1, except that.
[비교예 2] 내지 [비교예 7][Comparative Example 2] to [Comparative Example 7]
정공수송층 물질로 본 발명의 화합물 P1-1 대신 하기 비교화합물인 ref 1 내지 ref 6 중 하나를 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 one of the following comparative compounds ref 1 to ref 6 was used as the hole transport layer material instead of the compound P1-1 of the present invention.
<ref 1> <ref 2> <ref 3><ref 1> <ref 2> <ref 3>
Figure PCTKR2022003947-appb-I000071
Figure PCTKR2022003947-appb-I000071
<ref 4> <ref 5> <ref 6> <ref 4> <ref 5> <ref 6>
Figure PCTKR2022003947-appb-I000072
Figure PCTKR2022003947-appb-I000072
본 발명의 실시예 1 내지 실시예 27, 비교예 1 내지 비교예 7에 의해 제조된 유기전기발광소자에 순바이어스 직류전압을 가하여 포토리서치 (photoresearch) 사의 PR-650으로 전기발광(EL) 특성을 측정하였으며, 5000cd/m2 기준휘도에서 맥사이언스사의 수명측정장비를 통해 T95 수명을 측정하였다. 측정 결과는 하기 표 4와 같다.By applying a forward bias DC voltage to the organic electroluminescent devices manufactured by Examples 1 to 27 and Comparative Examples 1 to 7 of the present invention, the electroluminescence (EL) characteristics were obtained with PR-650 of Photoresearch. was measured, and the T95 lifetime was measured using a life measuring device of McScience at 5000 cd/m 2 standard luminance. The measurement results are shown in Table 4 below.
[표 4][Table 4]
Figure PCTKR2022003947-appb-I000073
Figure PCTKR2022003947-appb-I000073
Figure PCTKR2022003947-appb-I000074
Figure PCTKR2022003947-appb-I000074
상기 표 4에서 알 수 있는 것과 같이, 본 발명의 화합물을 정공수송층 재료로 사용할 경우, NPB나 비교화합물 ref 1 내지 ref 6 중 하나를 사용한 경우에 비해 유기전기소자의 구동전압이 낮아지고 효율 및 수명이 모두 향상되었다.As can be seen from Table 4, when the compound of the present invention is used as a material for the hole transport layer, the driving voltage of the organic electric device is lowered, and the efficiency and lifespan are lower than when one of NPB or comparative compounds ref 1 to ref 6 is used. All of these have been improved.
비교화합물인 ref 1 내지 ref 6은 모두 3차 아민구조라는 점에서 본 발명과 유사하지만, ref 1 및 ref 2는 아민그룹에 모두 순수한 아릴기가 치환되어 있는 반면, 본 발명의 화학식 1은 플루오렌 모이어티를 포함하는 축합환이 치환되어 있다는 점에서 상이하며, ref 3 내지 ref 6은 본 발명의 화합물과 매우 유사한 구조를 가지지만, ref 3, ref 4 및 ref 6은 페닐렌 모이어티에 결합된 링커 L과 나프탈렌 모이어티의 결합위치에 있어 본 발명의 화합물과 차이가 있고, ref 5는 L이 존재하지 않는다는 점에서 본 발명의 화합물과 차이가 있다. Comparative compounds ref 1 to ref 6 are similar to the present invention in that all have a tertiary amine structure, but ref 1 and ref 2 are all amine groups substituted with pure aryl groups, whereas Chemical Formula 1 of the present invention is a fluorene moiety It is different in that the condensed ring including t is substituted, and ref 3 to ref 6 have a structure very similar to the compound of the present invention, but ref 3, ref 4 and ref 6 are linked to a linker L bonded to a phenylene moiety. It is different from the compound of the present invention in the bonding position of the naphthalene moiety, and ref 5 is different from the compound of the present invention in that L is not present.
이에 대해 보다 상세히 설명하기 위해, 하기와 같이 본 발명의 화학식 1에서 L에 직접 결합된 페닐렌 모이어티를 구성 1이라 하고, 이러한 구성 1에 결합된 나프탈렌 모이어티를 구성 2라고 한다. In order to describe this in more detail, as follows, the phenylene moiety directly bonded to L in Formula 1 of the present invention is referred to as configuration 1, and the naphthalene moiety bonded to this configuration 1 is referred to as configuration 2.
Figure PCTKR2022003947-appb-I000075
Figure PCTKR2022003947-appb-I000075
본 발명의 화합물은 구성 1의 페닐렌에 링커 L과 구성 2가 오르쏘(ortho) 위치로 결합되어 있는 반면, ref 3, ref 4, ref 6은 링커 L과 구성 2가 메타(meta) 위치로 결합되어 있다는 점에서 차이가 있다. In the compound of the present invention, the linker L and the configuration 2 are bonded to the phenylene of configuration 1 in an ortho position, whereas ref 3, ref 4, and ref 6 are linked to the linker L and the configuration 2 in the meta position. The difference is that they are connected.
또한, 본 발명의 화합물은 링커 L이 단일결합이 될 수 없으므로 아민그룹의 질소와 구성 1이 링커 L을 매개로 결합되는 반면, ref 5는 구성 1인 페닐렌이 아민그룹의 질소에 직접 연결되어 있다는 점에서 차이가 있다.In addition, in the compound of the present invention, since the linker L cannot be a single bond, the nitrogen of the amine group and component 1 are bonded through the linker L, whereas in ref 5, the phenylene of the component 1 is directly connected to the nitrogen of the amine group. There is a difference in that there is
따라서, 아민그룹에 순수한 아릴기만 치환된 경우보다 특정 고리 형태(플루오렌일기 모이어티, 잔텐 모이어티, 싸이오잔텐 모이어티, 아크리딘 모이어티)를 포함하는 치환체가 치환되고, 아민그룹의 질소와 구성 1이 링커 L을 매개로 간접적으로 결합되면서 L과 구성 2가 구성 1에 메타 위치로 결합하는 본 발명의 화합물을 정공수송층 재료로 사용시 구동전압은 낮추면서 효율과 수명은 동시에 향상되는 것으로 보아, 코어의 종류 및 화합물을 구성하는 치환기의 종류 등이 소자의 전기적 특성에 영향을 미치는 것을 알 수 있다.Therefore, a substituent containing a specific ring form (fluorenyl group moiety, xanthene moiety, thioxanthene moiety, acridine moiety) is substituted rather than a case in which pure aryl groups are substituted in the amine group, and the nitrogen of the amine group is substituted. When using the compound of the present invention, in which constituent 1 and constituent 1 are indirectly coupled through the linker L, and in which L and constituent 2 are meta-positioned to constituent 1, as a hole transport layer material, the efficiency and lifetime are simultaneously improved while lowering the driving voltage. , it can be seen that the type of core and the type of substituents constituting the compound affect the electrical characteristics of the device.
ref 1과 본 발명의 화합물 P1-49, P2-25, P3-22, P5-16, P5-17의 HOMO 에너지 레벨을 비교해보면 하기 표 5와 같다.Comparing the HOMO energy levels of ref 1 and the compounds P1-49, P2-25, P3-22, P5-16, and P5-17 of the present invention is shown in Table 5 below.
[표 5][Table 5]
Figure PCTKR2022003947-appb-I000076
Figure PCTKR2022003947-appb-I000076
표 5을 참조해보면, ref 1에 비해 본 발명의 화합물 P1-49, P2-25, P3-22, P5-16, P5-17의 HOMO 에너지 레벨 값이 더 높은 것을 알 수 있다. 이는 화합물의 코어 구조에 따라 물성이 달라짐을 시사하며, 본 발명의 화학식 1로 표시되는 화합물을 정공수송층 재료로 사용할 경우, 정공주입층에서 발광층으로 정공이 용이하게 이동할 수 있으므로 ref 1 화합물에 비해 소자의 특성이 향상된 것으로 보인다.Referring to Table 5, it can be seen that the HOMO energy level values of the compounds P1-49, P2-25, P3-22, P5-16, and P5-17 of the present invention are higher than that of ref 1. This suggests that physical properties vary depending on the core structure of the compound, and when the compound represented by Formula 1 of the present invention is used as a material for the hole transport layer, holes can easily move from the hole injection layer to the light emitting layer, so the device compared to the ref 1 compound appears to have improved properties.
또한, 이미 설명한 것과 같이, ref 3, ref 4 및 ref 6과 본 발명 화합물 P1-34, P1-49 및 P5-16은 구성 1인 페닐렌에 링커 L과 구성 2가 결합된 위치에 있어 차이가 있는데, 그 결과 본 발명의 화합물은 비교화합물 대비 공명구조를 가지기 용이하므로, 본 발명의 화합물을 사용한 실시예의 소자 특성이 향상된 것으로 보인다.In addition, as already described, ref 3, ref 4 and ref 6 and the compounds P1-34, P1-49 and P5-16 of the present invention differ in the position where the linker L and the configuration 2 are bonded to the phenylene of configuration 1. However, as a result, since the compound of the present invention is easier to have a resonance structure compared to the comparative compound, it seems that the device characteristics of the Example using the compound of the present invention are improved.
또한, 이미 설명한 것과 같이, 비교화합물 ref 6과 본 발명의 화합물 P4-27은 아민그룹의 N과 구성 1 사이에 링커 L이 존재하는지 여부에 있어 차이가 있는데, 이러한 차이점으로 인해 하기 표 6과 같이 HOMO 값이 달라진다.In addition, as already described, there is a difference between the comparative compound ref 6 and the compound P4-27 of the present invention in whether a linker L exists between the N of the amine group and the component 1, due to this difference, as shown in Table 6 below The HOMO value is different.
[표 6][Table 6]
Figure PCTKR2022003947-appb-I000077
Figure PCTKR2022003947-appb-I000077
상기 표 6에서 알 수 있는 것과 같이, 본 발명의 화합물 P4-27의 HOMO 에너지 레벨이 ref 6보다 높으며, 이는 연결기의 유무가 화합물의 물성에 영향을 미치는 것을 알 수 있으며, HOMO 에너지 레벨이 높은 본 발명의 화합물을 정공수송층 재료로 사용할 경우, 정공주입층에서 발광층으로 정공이 용이하게 이동할 수 있으므로 ref 6 대비 소자의 특성이 향상된 것으로 보인다.As can be seen in Table 6, the HOMO energy level of the compound P4-27 of the present invention is higher than ref 6, which shows that the presence or absence of a linking group affects the physical properties of the compound, and the HOMO energy level is high When the compound of the present invention is used as a material for the hole transport layer, since holes can easily move from the hole injection layer to the light emitting layer, it seems that the characteristics of the device are improved compared to ref 6 .
따라서, 아민그룹에 치환된 치환기의 종류, 아민그룹의 N과 구성 1 간의 링커 L의 유무, 구성 1에 링커 L과 구성 2가 결합된 위치 등에 따라 화합물의 물성(HOMO, LUMO 및 T1 등) 등이 달라지고 이러한 차이는 유기전기소자의 성능에 유의미한 영향을 미치는 것을 알 수 있다. Therefore, the physical properties of the compound (HOMO, LUMO and T1, etc.) depending on the type of substituent substituted for the amine group, the presence or absence of the linker L between the N of the amine group and the component 1, the position where the linker L and the component 2 are bonded to the component 1, etc. It can be seen that this change has a significant effect on the performance of the organic electric device.
[실시예 28] 청색유기전기발광소자 (발광보조층)[Example 28] Blue organic electroluminescent device (light emitting auxiliary layer)
유리 기판에 형성된 ITO층(양극) 상에 2-TNATA를 60nm 두께로 진공증착하여 정공주입층을 형성한 후, 상기 정공주입층 상에 NPB를 60 nm 두께로 진공증착하여 정공수송층을 형성하였다.After vacuum deposition of 2-TNATA to a thickness of 60 nm on the ITO layer (anode) formed on the glass substrate to form a hole injection layer, NPB was vacuum deposited on the hole injection layer to a thickness of 60 nm to form a hole transport layer.
이어서, 상기 정공수송층 상에 본 발명의 화합물 P1-2를 20nm의 두께로 진공증착하여 발광보조층을 형성한 후, 상기 발광보조층 상에 호스트로 9,10-di(naphthalen-2-yl)anthracene, 도판트로 BD-052X(Idemitsu kosan 제조)를 96:4의 중량비로 사용하여 30 nm 두께의 발광층을 형성하였다.Then, on the hole transport layer, the compound P1-2 of the present invention was vacuum-deposited to a thickness of 20 nm to form a light-emitting auxiliary layer, and then, 9,10-di(naphthalen-2-yl) as a host on the light-emitting auxiliary layer. Anthracene and BD-052X (manufactured by Idemitsu Kosan) as a dopant were used in a weight ratio of 96:4 to form a light emitting layer with a thickness of 30 nm.
이어서, 상기 발광층 상에 BAlq를 10 nm 두께로 진공증착하여 정공저지층을 형성하고, 상기 정공저지층 상에 Alq3를 40 nm 두께로 진공증착하여 전자수송층을 형성하였다. 이후, 상기 전자수송층 상에 LiF를 0.2 nm 두께로 증착하여 전자주입층을 형성하고, 상기 전자주입층 상에 Al을 150 nm의 두께로 증착하여 음극을 형성하였다.Subsequently, BAlq was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and Alq 3 was vacuum deposited to a thickness of 40 nm on the hole blocking layer to form an electron transport layer. Thereafter, LiF was deposited on the electron transport layer to a thickness of 0.2 nm 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.
[실시예 29] 내지 [실시예 41][Example 29] to [Example 41]
발광보조층 물질로 본 발명의 화합물 P1-2 대신 하기 표 7에 기재된 본 발명의 화합물을 사용한 점을 제외하고는 상기 실시예 28과 동일한 방법으로 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 28, except that the compound of the present invention described in Table 7 was used instead of the compound P1-2 of the present invention as a light emitting auxiliary layer material.
[비교예 8][Comparative Example 8]
발광보조층을 형성하지 않은 점을 제외하고는 상기 실시예 28과 동일한 방법으로 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 28, except that the light-emitting auxiliary layer was not formed.
[비교예 9] 내지[비교예 14][Comparative Example 9] to [Comparative Example 14]
발광보조층 물질로 본 발명의 화합물 P1-2 대신 하기 표 7과 같이 ref 1 내지 ref 6 중 하나를 사용한 점을 제외하고는 상기 실시예 28과 동일한 방법으로 유기전기발광소자를 제작하였다.An organic electroluminescent device was manufactured in the same manner as in Example 28, except that one of ref 1 to ref 6 was used as the light emitting auxiliary layer material instead of the compound P1-2 of the present invention as shown in Table 7 below.
이와 같이 제조된 실시예 28 내지 실시예 41 및 비교예 8 내지 비교예 14의 유기전기발광소자에 순바이어스 직류전압을 가하여 포토리서치 (photoresearch) 사의 PR-650으로 전기발광(EL) 특성을 측정하였으며, 500cd/m2 기준휘도에서 맥사이언스사의 수명측정장비를 통해 T95 수명을 측정하였다. 측정 결과는 하기 표 7와 같다.A forward bias DC voltage was applied to the organic electroluminescent devices of Examples 28 to 41 and Comparative Examples 8 to 14 prepared in this way, and electroluminescence (EL) characteristics were measured with a PR-650 manufactured by photoresearch. , at 500cd/m 2 standard luminance, the T95 lifespan was measured using the life measuring equipment of McScience. The measurement results are shown in Table 7 below.
[표 7][Table 7]
Figure PCTKR2022003947-appb-I000078
Figure PCTKR2022003947-appb-I000078
상기 표 7로부터 알 수 있듯이, 본 발명의 화합물을 발광보조층 재료로 사용할 경우, 발광보조층을 형성하지 않거나 비교화합물 ref 1 내지 ref 6 중 하나를 사용한 경우에 비해 유기전기소자의 특성히 향상되었다.As can be seen from Table 7, when the compound of the present invention is used as a material for the light-emitting auxiliary layer, the characteristics of the organic electric device are improved compared to the case where the light-emitting auxiliary layer is not formed or when one of the comparative compounds ref 1 to ref 6 is used. .
즉, 아민그룹에 특정 고리 형태의 치환기(플루오렌 모이어티, 잔텐 모이어티, 싸이오잔텐 모이어티 등)가 치환되고, 상술한 바와 같은 특징을 갖는 본 발명의 화합물을 정공수송층 재료로뿐만 아니라 발광보조층 재료로 사용하더라도 소자의 특성이 향상되는 것을 알 수 있다. That is, a specific ring-type substituent (fluorene moiety, xanthene moiety, thioxanthene moiety, etc.) is substituted on the amine group, and the compound of the present invention having the above-described characteristics is used as a hole transport layer material as well as light emission. It can be seen that the properties of the device are improved even when it is used as an auxiliary layer material.
따라서, 본 발명의 화합물은 발광층 내 전하 균형을 보다 좋게 하여 효율을 향상시키고, 발광층으로부터 전자가 넘어오는 것을 저지함에 따라, 발광층 내 전하 균형을 유지시키며 이로 인해 구동전압과 수명 또한 향상시키는 것을 알 수 있으며, 결국 상술한 본 발명 화합물의 특징은 소자의 성능 향상에 주요 인자로 작용하는 것을 알 수 있다.Therefore, it can be seen that the compound of the present invention improves the efficiency by better balancing the charge in the light emitting layer, and prevents electrons from passing through the light emitting layer, thereby maintaining the charge balance in the light emitting layer, thereby improving the driving voltage and lifespan. In the end, it can be seen that the above-described characteristics of the compound of the present invention act as a major factor in improving the performance of the device.
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 권리범위가 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 merely 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 intended to illustrate, not to limit the present invention, and the scope of the present invention is not limited by these embodiments. The protection scope of the present invention should be construed by the following claims, and all technologies within the scope equivalent thereto should be construed as being included in the scope of the present invention.

Claims (16)

  1. 하기 화학식 1로 표시되는 화합물:A compound represented by the following formula (1):
    <화학식 1><Formula 1>
    Figure PCTKR2022003947-appb-I000079
    Figure PCTKR2022003947-appb-I000079
    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~C20의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C20의 알콕시기; C6~C20의 아릴옥시기; 및 -L'-N(Ra)(Rb)로 이루어진 군에서 선택되고, 이웃한 기끼리 서로 결합하여 고리를 형성할 수 있고,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 P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; C 3 ~ C 60 An aliphatic group; C 1 ~ C 20 Alkyl group; C 2 ~ C 20 Alkenyl group; C 2 ~ C 20 Alkynyl group; C 1 ~ C 20 Alkoxy group; C 6 ~ C 20 Aryloxy group; And -L'-N(R a ) (R b ) is selected from the group consisting of, adjacent groups may combine with each other to form a ring,
    a 내지 c는 각각 0~4의 정수이고, d는 0~7의 정수이고, 이들 각각이 2 이상의 정수인 경우, R1 각각, R2 각각, R3 각각, R4 각각은 서로 같거나 상이하며,a to c are each an integer of 0-4, d is an integer of 0-7, and when each of these 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 as or different from each other, ,
    R' 및 R"은 서로 독립적으로 수소; C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; C1~C20의 알킬기; C2~C20의 알켄일기; C2~C20의 알킨일기; C1~C20의 알콕시기; 및 C6~C20의 아릴옥시기로 이루어진 군에서 선택되고, R'과 R"이 서로 결합하여 고리를 형성할 수 있고,R' and R" are each independently hydrogen; C 6 ~ C 60 Aryl group; Fluorenyl group; C 2 ~ C 60 Heterocycle containing at least one heteroatom of O, N, S, Si and P group; C 3 ~ C 60 aliphatic ring group; C 1 ~ C 20 alkyl group; C 2 ~ C 20 alkenyl group; C 2 ~ C 20 alkynyl group; C 1 ~ C 20 alkoxy group; and C 6 -C 20 is selected from the group consisting of an aryloxy group, R' and R" may combine with each other to form a ring,
    L은 C6~C60의 아릴렌기; 플루오렌일렌기; C3~C60의 지방족고리기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; 및 이들의 조합으로 이루어진 군에서 선택되며,L is C 6 ~ C 60 Arylene group; fluorenylene group; C 3 ~ C 60 aliphatic group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; And selected from the group consisting of combinations thereof,
    Ar1은 C6~C60의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C60의 헤테로고리기; C3~C60의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택되고,Ar 1 is a C 6 ~ C 60 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; C 3 ~ C 60 aliphatic group; And selected from the group consisting of combinations thereof,
    상기 L'은 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,The L' is a single bond; C 6 ~ C 60 Arylene group; fluorenylene group; C 3 ~ C 60 aliphatic group; And O, N, S, Si and P, including at least one heteroatom C 2 ~ C 60 It is selected from the group consisting of a heterocyclic group,
    상기 Ra 및 Rb는 서로 독립적으로 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 선택되고,The R a and R b are each independently of each other, independently of each other, a C 6 ~ C 60 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 60 A heterocyclic group; And C 3 ~ C 60 It is selected from the group consisting of an aliphatic cyclic group,
    상기 아릴기, 아릴렌기, 플루오렌일기, 플루오렌일렌기, 헤테로고리기, 지방족 고리기, 알킬기, 알켄일기, 알킨일기, 알콕시기, 아릴옥시기, 이웃한 기끼리 서로 결합하여 형성된 고리, R'과 R"이 서로 결합하여 형성된 고리, R1과 R2가 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; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C30의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C30의 헤테로고리기; C3-C30의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택된 하나 이상의 치환기로 치환될 수 있다.The aryl group, an arylene group, a fluorenyl group, a fluorenylene group, a heterocyclic group, an aliphatic ring group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, a ring formed by bonding adjacent groups to each other, R A ring formed by bonding ' and R" to each other, and a ring formed by bonding R 1 and R 2 to each other are each deuterium; halogen; C 1 -C 20 alkyl group or C 6 -C 20 aryl group substituted or unsubstituted silane Group; C 1 -C 20 Alkyl group or C 6 -C 20 aryl group substituted or unsubstituted phosphine oxide; Siloxane group; Cyano group; Nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 Alkoxy group; C 6 -C 20 Aryloxy group; C 6 -C 20 Arylthio group; C 1 -C 20 Alkyl group; C 2 -C 20 Alkenyl group; C 2 -C 20 Alkynyl group C 6 -C 30 Aryl group; Fluorenyl group; C 2 -C 30 Heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C It may be substituted with one or more substituents selected from the group consisting of an aliphatic ring group of 30 ;
  2. 제 1항에 있어서, The method of claim 1,
    상기 화학식 1은 하기 화학식 2 내지 화학식 4 중 하나로 표시되는 화합물:Chemical Formula 1 is a compound represented by one of the following Chemical Formulas 2 to 4:
    <화학식 2> <화학식 3><Formula 2> <Formula 3>
    Figure PCTKR2022003947-appb-I000080
    Figure PCTKR2022003947-appb-I000080
    <화학식 4><Formula 4>
    Figure PCTKR2022003947-appb-I000081
    Figure PCTKR2022003947-appb-I000081
    상기 화학식 2 내지 화학식 4에서, R1, R2, R4, R', R", Ar1, a, b, d는 제1항에서 정의된 것과 같다.In Formulas 2 to 4, R 1 , R 2 , R 4 , R′, R″, Ar 1 , a, b, and d are the same as defined in claim 1.
  3. 제 1항에 있어서, The method of claim 1,
    상기 화학식 1은 하기 화학식 5 또는 화학식 6으로 표시되는 화합물:Formula 1 is a compound represented by Formula 5 or Formula 6:
    <화학식 5> <화학식 6><Formula 5> <Formula 6>
    Figure PCTKR2022003947-appb-I000082
    Figure PCTKR2022003947-appb-I000082
    상기 화학식 5 및 화학식 6에서, R1, R2, R', R", Ar1, a, b는 제1항에서 정의된 것과 같고, In Formulas 5 and 6, R 1 , R 2 , R′, R″, Ar 1 , a, b are the same as defined in claim 1,
    R5는 수소; 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; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C30의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C30의 헤테로고리기; C3-C30의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택되며, 이웃한 기끼리 서로 결합하여 고리를 형성할 수 있고,R 5 is hydrogen; heavy hydrogen; halogen; a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Phosphine oxide unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; siloxane group; cyano group; nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 Alkoxy group; C 6 -C 20 aryloxy group; C 6 -C 20 An arylthio group; C 1 -C 20 Alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkynyl group; C 6 -C 30 Aryl group; fluorenyl group; C 2 -C 30 A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C 30 An aliphatic group; And it is selected from the group consisting of combinations thereof, and adjacent groups may combine with each other to form a ring,
    e는 0~5의 정수이고, e가 2 이상의 정수인 경우 R5 각각은 서로 같거나 상이하다.e is an integer of 0 to 5, and when e is an integer of 2 or more, each of R 5 is the same as or different from each other.
  4. 제 1항에 있어서, The method of claim 1,
    상기 화학식 1은 하기 화학식 7 내지 화학식 10 중 하나로 표시되는 화합물:Formula 1 is a compound represented by one of the following Formulas 7 to 10:
    <화학식 7> <화학식 8><Formula 7> <Formula 8>
    Figure PCTKR2022003947-appb-I000083
    Figure PCTKR2022003947-appb-I000083
    <화학식 9> <화학식 10><Formula 9> <Formula 10>
    Figure PCTKR2022003947-appb-I000084
    Figure PCTKR2022003947-appb-I000084
    상기 화학식 7 내지 화학식 10에서, R1 내지 R4, R', R", Ar1, L, a, c, d는 제1항에서 정의된 것과 같고, In Formulas 7 to 10, R 1 to R 4 , R', R", Ar 1 , L, a, c, d are the same as defined in claim 1,
    R11 내지 R15는 서로 독립적으로 수소; 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; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C30의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C30의 헤테로고리기; C3-C30의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택되며, 이웃한 기끼리 서로 결합하여 고리를 형성할 수 있고, R 11 to R 15 are each independently hydrogen; heavy hydrogen; halogen; a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Phosphine oxide unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; siloxane group; cyano group; nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 Alkoxy group; C 6 -C 20 aryloxy group; C 6 -C 20 An arylthio group; C 1 -C 20 Alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkynyl group; C 6 -C 30 Aryl group; fluorenyl group; C 2 -C 30 A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C 30 An aliphatic group; And it is selected from the group consisting of combinations thereof, and adjacent groups may combine with each other to form a ring,
    화학식 7 및 화학식 8에서, b는 0~3의 정수이고, 화학식 9 및 화학식 10에서, b는 0~4의 정수이며, b가 2 이상의 정수인 경우 R2 각각은 서로 같거나 상이하며,In Formulas 7 and 8, b is an integer of 0 to 3, in Formulas 9 and 10, b is an integer of 0 to 4, and when b is an integer of 2 or more, each of R 2 is the same as or different from each other,
    m, n, o 및 p는 각각 0~4의 정수이고, q는 0~3의 정수이며, 이들 각각이 2 이상의 정수인 경우 R11 각각, R12 각각, R13 각각, R14 각각, R15 각각은 서로 같거나 상이하다.m, n, o and p are each an integer from 0 to 4, q is an integer from 0 to 3, and when each of these is an integer of 2 or greater, each of R 11 , each of R 12 , each of R 13 , each of R 14 , and R 15 each is the same as or different from each other.
  5. 제 1항에 있어서,The method of claim 1,
    상기 화학식 1은 하기 화학식 11 내지 화학식 14 중 하나로 표시되는 화합물:Formula 1 is a compound represented by one of the following Formulas 11 to 14:
    <화학식 11> <화학식 12><Formula 11> <Formula 12>
    Figure PCTKR2022003947-appb-I000085
    Figure PCTKR2022003947-appb-I000085
    <화학식 13> <화학식 14><Formula 13> <Formula 14>
    Figure PCTKR2022003947-appb-I000086
    Figure PCTKR2022003947-appb-I000086
    상기 화학식 11 내지 화학식 14에서, R1 내지 R4, R', R", a, c, d는 제1항에서 정의된 것과 같고, *는 결합위치를 나타내며,In Formulas 11 to 14, R 1 to R 4 , R', R", a, c, and d are the same as defined in claim 1, and * represents a bonding position,
    X는 O, S, N(Ar1) 또는 C(R1)(R2)이며,X is O, S, N(Ar 1 ) or C(R 1 )(R 2 ),
    R5, R6, R11 내지 R15, R1 및 R2는 서로 독립적으로 수소; 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; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C30의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C30의 헤테로고리기; C3-C30의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택되며, 이웃한 기끼리 서로 결합하여 고리를 형성할 수 있고, R1과 R2가 서로 결합하여 고리를 형성할 수 있으며,R 5 , R 6 , R 11 to R 15 , R 1 and R 2 are each independently hydrogen; heavy hydrogen; halogen; a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Phosphine oxide unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; siloxane group; cyano group; nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 Alkoxy group; C 6 -C 20 aryloxy group; C 6 -C 20 An arylthio group; C 1 -C 20 Alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkynyl group; C 6 -C 30 Aryl group; fluorenyl group; C 2 -C 30 A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C 30 An aliphatic group; And it is selected from the group consisting of combinations thereof, adjacent groups may be bonded to each other to form a ring, and R 1 and R 2 may be bonded to each other to form a ring,
    상기 Ar1은 C6~C30의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C30의 헤테로고리기; C3~C30의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택되고,The Ar 1 is a C 6 ~ C 30 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 30 A heterocyclic group; C 3 ~ C 30 of an aliphatic ring; And selected from the group consisting of combinations thereof,
    화학식 11 및 화학식 12에서, b는 0~3의 정수이고, 화학식 13 및 화학식 14에서, b는 0~4의 정수이며, b가 2 이상의 정수인 경우 R2 각각은 서로 같거나 상이하며,In Formulas 11 and 12, b is an integer of 0 to 3, in Formulas 13 and 14, b is an integer of 0 to 4, and when b is an integer of 2 or more, each R 2 is the same as or different from each other,
    e, m, n, o 및 p는 각각 0~4의 정수이고, f는 0~5의 정수이고, q는 0~3의 정수이며, 이들 각각이 2 이상의 정수인 경우 R5 각각, R6 각각, R11 각각, R12 각각, R13 각각, R14 각각, R15 각각은 서로 같거나 상이하다.e, m, n, o and p are each an integer from 0 to 4, f is an integer from 0 to 5, q is an integer from 0 to 3, and when each of these is an integer of 2 or more, each of R 5 and R 6 , each of R 11 , each of R 12 , each of R 13 , each of R 14 and each of R 15 are the same as or different from each other.
  6. 제 1항에 있어서,The method of claim 1,
    상기 화학식 1은 하기 화학식 15 또는 화학식 16으로 표시되는 화합물:Formula 1 is a compound represented by Formula 15 or Formula 16:
    <화학식 15> <화학식 16><Formula 15> <Formula 16>
    Figure PCTKR2022003947-appb-I000087
    Figure PCTKR2022003947-appb-I000087
    상기 화학식 15 및 화학식 16에서, R1, R2, R', R", a는 제1항에서 정의된 것과 같고, In Formulas 15 and 16, R 1 , R 2 , R′, R″, a are the same as defined in claim 1,
    R5 및 R6은 서로 독립적으로 수소; 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; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C30의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C30의 헤테로고리기; C3-C30의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택되며, 이웃한 기끼리 서로 결합하여 고리를 형성할 수 있고,R 5 and R 6 are each independently hydrogen; heavy hydrogen; halogen; a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Phosphine oxide unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; siloxane group; cyano group; nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 Alkoxy group; C 6 -C 20 aryloxy group; C 6 -C 20 An arylthio group; C 1 -C 20 Alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkynyl group; C 6 -C 30 Aryl group; fluorenyl group; C 2 -C 30 A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C 30 An aliphatic group; And it is selected from the group consisting of combinations thereof, and adjacent groups may combine with each other to form a ring,
    b는 0~3의 정수이고, e는 0~4의 정수이고, f는 0~5의 정수이고, 이들 각각이 2 이상의 정수인 경우 R2 각각, R5 각각, R6 각각은 서로 같거나 상이하다.b is an integer from 0 to 3, e is an integer from 0 to 4, f is an integer from 0 to 5, and when each of these is an integer of 2 or more, each of R 2 , each of R 5 , and each of R 6 are the same as or different from each other do.
  7. 제 1항에 있어서,The method of claim 1,
    상기 화학식 1은 하기 화학식 17 내지 화학식 22 중 하나로 표시되는 화합물:Formula 1 is a compound represented by one of the following Formulas 17 to 22:
    <화학식 17> <화학식 18><Formula 17> <Formula 18>
    Figure PCTKR2022003947-appb-I000088
    Figure PCTKR2022003947-appb-I000088
    <화학식 19> <화학식 20><Formula 19> <Formula 20>
    Figure PCTKR2022003947-appb-I000089
    Figure PCTKR2022003947-appb-I000089
    <화학식 21> <화학식 22><Formula 21> <Formula 22>
    Figure PCTKR2022003947-appb-I000090
    Figure PCTKR2022003947-appb-I000090
    상기 화학식 17 내지 화학식 22에서, R1, R2, R', a는 제1항에서 정의된 것과 같고, *는 결합위치를 나타내며,In Formulas 17 to 22, R 1 , R 2 , R′, a are the same as defined in claim 1, and * represents a bonding position,
    X는 O, S, N(Ar1) 또는 C(R1)(R2)이며,X is O, S, N(Ar 1 ) or C(R 1 )(R 2 ),
    R5, R6, R11 내지 R15, R1 및 R2는 서로 독립적으로 수소; 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; 시아노기; 니트로기; C1-C20의 알킬싸이오기; C1-C20의 알콕시기; C6-C20의 아릴옥시기; C6-C20의 아릴싸이오기; C1-C20의 알킬기; C2-C20의 알켄일기; C2-C20의 알킨일기; C6-C30의 아릴기; 플루오렌일기; O, N, S, Si 및 P로 이루어진 군에서 선택된 적어도 하나의 헤테로원자를 포함하는 C2-C30의 헤테로고리기; C3-C30의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택되며, 이웃한 기끼리 서로 결합하여 고리를 형성할 수 있고, R1과 R2는 서로 결합하여 고리를 형성할 수 있으며,R 5 , R 6 , R 11 to R 15 , R 1 and R 2 are each independently hydrogen; heavy hydrogen; halogen; a silane group unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; Phosphine oxide unsubstituted or substituted with a C 1 -C 20 alkyl group or a C 6 -C 20 aryl group; siloxane group; cyano group; nitro group; C 1 -C 20 Alkylthio group; C 1 -C 20 Alkoxy group; C 6 -C 20 aryloxy group; C 6 -C 20 An arylthio group; C 1 -C 20 Alkyl group; C 2 -C 20 alkenyl group; C 2 -C 20 alkynyl group; C 6 -C 30 Aryl group; fluorenyl group; C 2 -C 30 A heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; C 3 -C 30 An aliphatic group; And it is selected from the group consisting of combinations thereof, adjacent groups may combine with each other to form a ring, and R 1 and R 2 may combine with each other to form a ring,
    상기 Ar1은 C6~C30의 아릴기; 플루오렌일기; O, N, S, Si 및 P 중 적어도 하나의 헤테로원자를 포함하는 C2~C30의 헤테로고리기; C3~C30의 지방족고리기; 및 이들의 조합으로 이루어진 군에서 선택되고,The Ar 1 is a C 6 ~ C 30 aryl group; fluorenyl group; O, N, S, Si and P containing at least one heteroatom C 2 ~ C 30 A heterocyclic group; C 3 ~ C 30 of an aliphatic ring; And selected from the group consisting of combinations thereof,
    화학식 17 및 화학식 18에서, b는 0~3의 정수이고, 화학식 19 내지 화학식 22에서, b는 0~4의 정수이며, b가 2 이상의 정수인 경우 R2 각각은 서로 같거나 상이하며,In Formulas 17 and 18, b is an integer of 0 to 3, in Formulas 19 to 22, b is an integer of 0 to 4, and when b is an integer of 2 or more, each R 2 is the same as or different from each other,
    e, m, n, o 및 p는 각각 0~4의 정수이고, f는 0~5의 정수이고, q는 0~3의 정수이며, 이들 각각이 2 이상의 정수인 경우 R5 각각, R6 각각, R11 각각, R12 각각, R13 각각, R14 각각, R15 각각은 서로 같거나 상이하다.e, m, n, o and p are each an integer from 0 to 4, f is an integer from 0 to 5, q is an integer from 0 to 3, and when each of these is an integer of 2 or more, each of R 5 and R 6 , each of R 11 , each of R 12 , each of R 13 , each of R 14 and each of R 15 are the same as or different from each other.
  8. 제 1항에 있어서,The method of claim 1,
    상기 Ar1은 C12~C25의 아릴기 또는 플루오렌일기인 것을 특징으로 하는 화합물.The Ar 1 is a C 12 ~ C 25 compound, characterized in that the aryl group or fluorenyl group.
  9. 제 1항에 있어서, The method of claim 1,
    상기 화학식 1로 표시되는 화합물은 하기 화합물 중 하나인 것을 특징으로 하는 화합물:The compound represented by Formula 1 is a compound, characterized in that one of the following compounds:
    Figure PCTKR2022003947-appb-I000091
    Figure PCTKR2022003947-appb-I000091
    Figure PCTKR2022003947-appb-I000092
    Figure PCTKR2022003947-appb-I000092
    Figure PCTKR2022003947-appb-I000093
    Figure PCTKR2022003947-appb-I000093
    Figure PCTKR2022003947-appb-I000094
    Figure PCTKR2022003947-appb-I000094
    Figure PCTKR2022003947-appb-I000095
    Figure PCTKR2022003947-appb-I000095
    Figure PCTKR2022003947-appb-I000096
    Figure PCTKR2022003947-appb-I000096
    Figure PCTKR2022003947-appb-I000097
    Figure PCTKR2022003947-appb-I000097
    Figure PCTKR2022003947-appb-I000098
    Figure PCTKR2022003947-appb-I000098
    Figure PCTKR2022003947-appb-I000099
    .
    Figure PCTKR2022003947-appb-I000099
    .
  10. 제 1전극; 제 2전극; 상기 제 1전극과 상기 제 2전극 사이에 형성된 유기물층을 포함하는 유기전기소자에 있어서,a first electrode; a second electrode; In the organic electric device comprising an organic material layer formed between the first electrode and the second electrode,
    상기 유기물층은 제1항의 화합물을 포함하는 것을 특징으로 하는 유기전기소자.The organic material layer is an organic electric device comprising the compound of claim 1.
  11. 제 10항에 있어서,11. The method of claim 10,
    상기 유기물층은 발광층, 상기 발광층과 제 1전극 사이에 형성된 정공수송층 및 상기 정공수송층과 상기 제 1전극 사이에 형성된 발광보조층을 포함하며, 상기 화합물은 상기 정공수송층 및 발광보조층 중 적어도 하나의 층에 포함되는 것을 특징으로 하는 유기전기소자.The organic material layer includes a light emitting layer, a hole transport layer formed between the light emitting layer and the first electrode, and a light emitting auxiliary layer formed between the hole transport layer and the first electrode, wherein the compound is at least one of the hole transport layer and the light emission auxiliary layer. An organic electric device, characterized in that it is included in the.
  12. 제 10항에 있어서,11. The method of claim 10,
    상기 유기전기소자는 제1항의 화합물을 포함하는 광효율개선층을 더 포함하며,The organic electric device further comprises a light efficiency improvement layer comprising the compound of claim 1,
    상기 광효율개선층은 상기 제 1전극 또는 제 2전극의 양면 중에서 상기 유기물층과 접하지 않는 층에 형성되는 것을 특징으로 하는 유기전기소자.The light efficiency improving layer is an organic electric device, characterized in that formed on a layer not in contact with the organic material layer on both surfaces of the first electrode or the second electrode.
  13. 제 10항에 있어서,11. The method of claim 10,
    상기 유기물층은 상기 제 1전극 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, a light emitting layer, and an electron transport layer sequentially formed on the first electrode.
  14. 제 13항에 있어서,14. The method of claim 13,
    상기 유기물층은 상기 둘 이상의 스택 사이에 형성된 전하생성층을 더 포함하는 것을 특징으로 하는 유기전기소자.The organic material layer is an organic electric device, characterized in that it further comprises a charge generation layer formed between the two or more stacks.
  15. 제10항의 유기전기소자를 포함하는 디스플레이장치; 및 A display device comprising the organic electric device of claim 10; and
    상기 디스플레이장치를 구동하는 제어부;를 포함하는 전자장치.An electronic device comprising a; a control unit for driving the display device.
  16. 제 15항에 있어서,16. The method of claim 15,
    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 device for monochromatic lighting, and a device for a quantum dot display.
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