WO2024014660A1 - Compound and organic light-emitting device comprising same - Google Patents

Compound and organic light-emitting device comprising same Download PDF

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WO2024014660A1
WO2024014660A1 PCT/KR2023/004877 KR2023004877W WO2024014660A1 WO 2024014660 A1 WO2024014660 A1 WO 2024014660A1 KR 2023004877 W KR2023004877 W KR 2023004877W WO 2024014660 A1 WO2024014660 A1 WO 2024014660A1
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이성재
김민준
문현진
이형진
홍성길
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주식회사 엘지화학
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Priority to CN202380012850.0A priority Critical patent/CN117715890A/en
Publication of WO2024014660A1 publication Critical patent/WO2024014660A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole

Definitions

  • This specification relates to compounds and organic light-emitting devices containing the same.
  • organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials.
  • Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them.
  • the organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer.
  • a voltage is applied between the two electrodes
  • holes are injected from the anode and electrons from the cathode into the organic material layer.
  • an exciton is formed, and this exciton is When it falls back to the ground state, it glows.
  • This specification provides a compound and an organic light-emitting device containing the same.
  • An exemplary embodiment of the present specification provides a compound of Formula 1 below.
  • Ar1 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted monocyclic aryl group,
  • R1 to R3 and R5 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or one or more adjacent pairs are combined with each other to form a substituted or unsubstituted ring,
  • R4 is deuterium; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or one or more adjacent pairs are bonded to each other to form a substituted or unsubstituted ring,
  • At least one adjacent pair of at least one of R6 to R8 is bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring, and at least one adjacent pair of at least one of R6 to R8 is bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring.
  • the remainders that do not form an aromatic hydrocarbon ring are the same or different, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • r1 to r7 are each integers from 1 to 4,
  • r8 is an integer from 1 to 5
  • At least one of r6 to r8 is 2 or more,
  • R2 of 2 or more is the same or different from each other
  • r3 is 2 or more, the 2 or more R3s are the same or different from each other,
  • r8 is 2 or more, the 2 or more R8s are the same or different from each other.
  • the present specification includes a first electrode; second electrode; and an organic light emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer contains the compound.
  • the compounds described in this specification can be used as a material for the organic layer of an organic light-emitting device.
  • a compound according to at least one embodiment of the present specification may improve efficiency, low driving voltage, and/or lifespan characteristics in an organic light-emitting device.
  • the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection materials. Additionally, compared to existing organic light emitting devices, they have the effects of low driving voltage, high efficiency, and/or long lifespan.
  • 1 and 2 show examples of organic light-emitting devices according to an exemplary embodiment of the present specification.
  • the compound of Formula 1 has a structure in which carbazole is substituted in the ortho position on the benzene ring, and conjugation is better than the structure in which carbazole is substituted in the meta or para position. Because it is in a broken state, the band gap is large, making it relatively easy to control the HOMO and LUMO values depending on the type of substituent. In addition, since it has a substituent other than hydrogen at the R4 position, it is a structure in which it is easy to control the HOMO and LUMO levels by adjusting the conjugation length. Therefore, the organic light-emitting device containing the compound of Formula 1 has the characteristics of low driving voltage, excellent efficiency, and long lifespan.
  • the term "combination thereof" included in the Markushi format expression means a mixture or combination of one or more components selected from the group consisting of the components described in the Markushi format expression, It means including one or more selected from the group consisting of.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent.
  • the position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.
  • substituted or unsubstituted refers to deuterium; halogen group; Cyano group; Alkyl group; Cycloalkyl group; Alkoxy group; alkenyl group; Haloalkyl group; silyl group; boron group; Amine group; Aryl group; Condensed ring groups of aromatic hydrocarbon rings and aliphatic hydrocarbon rings; It means that it is substituted with one or more substituents selected from the group consisting of a heteroaryl group, is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituents.
  • linking two or more substituents means that the hydrogen of one substituent is linked to another substituent.
  • a phenyl group and a naphthyl group are connected. or It can be a substituent of .
  • connecting three substituents not only means that (substituent 1) - (substituent 2) - (substituent 3) are connected in succession, but also (substituent 2) and (substituent 3) are connected to (substituent 1).
  • phenyl group, naphthyl group and isopropyl group are connected , , or It can be a substituent of .
  • the above definition equally applies to those in which 4 or more substituents are connected.
  • examples of the halogen group include fluorine, chlorine, bromine, or iodine.
  • the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group,
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically includes cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, and 2,3-dimethylcyclo group.
  • Pentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, Cycloheptyl group, cyclooctyl group, adamantyl group, etc. are included, but are not limited thereto.
  • the alkoxy group may be straight chain, branched chain, or ring chain.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms.
  • methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, Isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group, benzyloxy group, p -It may be a methylbenzyloxy group, etc., but is not limited thereto.
  • the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30.
  • Specific examples include vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1 -Butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but is not limited thereto. .
  • haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group in the definition of the alkyl group.
  • the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. It is preferable to have 10 to 30 carbon atoms.
  • the polycyclic aryl group may be a naphthyl group, anthracene group, phenanthrene group, triphenylene group, pyrene group, phenalene group, perylene group, chrysene group, fluorene group, etc., but is not limited thereto.
  • the fluorene group may be substituted, and adjacent groups may combine with each other to form a ring.
  • fluorene group examples include etc., but is not limited to this.
  • an “adjacent” group may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the substituent in terms of structure, or another substituent substituted on the atom on which the substituent is substituted. You can. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as “adjacent” groups.
  • the heteroaryl group includes one or more non-carbon atoms and heteroatoms.
  • the heteroaryl group may include one or more atoms selected from the group consisting of O, N, Se, and S. .
  • the number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic.
  • heteroaryl groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, and acridine group.
  • pyridazine group pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benzyl group.
  • the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, etc.
  • alkylsilyl groups examples of the alkyl group described above may be applied to the alkyl group
  • examples of the aryl group described above may be applied to the aryl group among the arylsilyl groups
  • examples of the heteroaryl group among the heteroarylsilyl groups may apply to the heteroaryl group. can be applied.
  • the boron group may be -BR 100 R 101 , and R 100 and R 101 are the same or different, and are each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • the boron group specifically includes, but is not limited to, dimethyl boron group, diethyl boron group, t-butylmethyl boron group, and diphenyl boron group.
  • the amine group is a group consisting of -NH 2 , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group. It may be selected from, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group.
  • diphenylamine group ditolylamine group, N-phenyltolylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group; N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthre
  • Examples include, but are not limited to, a nylfluorenylamine group and an N-biphenylfluorenylamine group.
  • the N-alkylarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and an aryl group.
  • the alkyl group and aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and aryl group described above.
  • the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted at the N of the amine group.
  • the aryl group and heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and heteroaryl group described above.
  • the N-alkylheteroarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and a heteroaryl group.
  • the alkyl group and heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the alkyl group and heteroaryl group described above.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group.
  • the arylamine group containing two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group simultaneously.
  • the aryl group in the arylamine group may be selected from the examples of aryl groups described above.
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group.
  • the heteroarylamine group containing two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group simultaneously.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of heteroaryl groups described above.
  • the hydrocarbon ring group is an aromatic hydrocarbon ring group; Aliphatic hydrocarbon ring group; Alternatively, it may be a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring.
  • the description of the aryl group described above may be applied to the aromatic hydrocarbon ring group, and the description of the cycloalkyl group described above may be applied to the aliphatic hydrocarbon ring group.
  • the condensed ring group of the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring may have a structure in which the above-mentioned aryl group and cycloalkyl group are condensed with each other.
  • the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and, except for those that are not monovalent, the cycloalkyl group, the aryl group, and combinations thereof.
  • hydrocarbon ring is benzene, cyclohexane, adamantane, bicyclo[2.2.1]heptane, bicyclo[2.2.1]octane, tetrahydronaphthalene, tetrahydroanthracene, 1,2 , 3,4-tetrahydro-1,4-methanonaphthalene, 1,2,3,4-tetrahydro-1,4-ethanonaphthalene, spirocyclopentane fluorene, spiroadamantane fluorene, and spiro Cyclohexane fluorene, etc., but is not limited to this.
  • the heterocycle includes one or more non-carbon atoms and heteroatoms.
  • the heterocycle may include one or more atoms selected from the group consisting of O, N, Se, and S.
  • the heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of heteroaryl groups among the heterocyclic groups, except that the aromatic heterocycle is not monovalent. there is.
  • the aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. In addition, it refers to a heterocycle excluding an aromatic heterocycle, and a heterocycle that contains a double bond but is not aromatic is an aliphatic heterocycle.
  • aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, and azocaine.
  • thiocane tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran, but are not limited thereto.
  • the aliphatic heterocycle (group) refers to an aliphatic ring (group) containing one or more heteroatoms. In addition, it refers to a heterocycle (group) excluding an aromatic heterocycle (group), and a heterocycle (group) that contains a double bond but is not aromatic is an aliphatic heterocycle (group).
  • examples of the aliphatic or aromatic-aliphatic condensed heterocycle include tetrahydrobenzonaphthothiophene and tetrahydrobenzonaphthofuran, but are not limited thereto.
  • the portion in Formula 1 where a substituent is not indicated may mean that hydrogen or deuterium has been substituted.
  • R1 is hydrogen
  • R2 is hydrogen
  • R3 is hydrogen
  • R1 is deuterium
  • R2 is deuterium
  • R3 is deuterium
  • Formula 1 is the following Formula 1-1.
  • R2, R4 to R8, r2, r4 to r8, and Ar1 are the same as those defined in Formula 1 above.
  • R2 is hydrogen; heavy hydrogen; Or, it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or one or more adjacent pairs are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • R2 is hydrogen; heavy hydrogen; Or, it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or one or more adjacent pairs are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R2 is hydrogen; heavy hydrogen; Alternatively, it is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or one or more adjacent pairs are bonded to each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • R2 is hydrogen; Alternatively, it is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or one or more adjacent pairs are bonded to each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R2 is hydrogen; heavy hydrogen; Or it is a phenyl group, or one or more adjacent pairs combine with each other to form benzene.
  • R2 is hydrogen; heavy hydrogen; Or, it is a phenyl group, or any adjacent pair combines with each other to form benzene.
  • R1 is hydrogen; heavy hydrogen; Or, it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or one or more adjacent pairs are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • R1 is hydrogen; heavy hydrogen; Or, it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or one or more adjacent pairs are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R1 is hydrogen; heavy hydrogen; Alternatively, it is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or one or more adjacent pairs are bonded to each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • R1 is hydrogen; Alternatively, it is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or one or more adjacent pairs are bonded to each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R1 is hydrogen; heavy hydrogen; Or it is a phenyl group, or one or more adjacent pairs combine with each other to form benzene.
  • R1 is hydrogen; heavy hydrogen; Or, it is a phenyl group, or any adjacent pair combines with each other to form benzene.
  • Formula 1 is any one of the following Formulas 1-2 to 1-5.
  • R1, R3 to R8, r1, r3 to r8 and Ar1 are the same as those defined in Formula 1 above,
  • R'2 and R21 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • r'2 is an integer from 1 to 4,
  • r21 is an integer from 1 to 6
  • R'2 When r'2 is 2 or more, R'2 of 2 or more is the same as or different from each other,
  • r21 is 2 or more
  • the 2 or more R21s are the same or different from each other.
  • Formula 1 is any one of the following Formulas 1-6 to 1-9.
  • R4 to R8, r4 to r8 and Ar1 are the same as those defined in Formula 1 above,
  • R'2 is hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • r'2 is an integer from 1 to 4,
  • R'2 of 2 or more is the same or different from each other.
  • Formula 1 is any one of the following Formulas 1-10 to 1-12.
  • R2, r2, R4, r4, R5, r5 and Ar1 are the same as those defined in Formula 1 above,
  • R'6 One or more adjacent pairs of R'6 combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring, and the remainder is hydrogen; or deuterium,
  • R'7 One or more adjacent pairs of R'7 combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring, and the remainder is hydrogen; or deuterium,
  • R'8 One or more adjacent pairs of R'8 combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring, and the remainder is hydrogen; or deuterium,
  • r'6 is an integer of 2 to 4, and when r'6 is 2 or more, R'6 of 2 or more is the same as or different from each other,
  • r'7 is an integer of 2 to 4, and when r'7 is 2 or more, R'7 of 2 or more is the same as or different from each other,
  • r'8 is an integer of 2 to 5, and when r'8 is 2 or more, R' of 2 or more is the same or different.
  • R4 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R4 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • R4 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.
  • R4 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R4 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • R4 is a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.
  • R4 is a phenyl group.
  • r4 is 1.
  • R5 is hydrogen; heavy hydrogen; Or, it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or one or more adjacent pairs are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • R5 is hydrogen; heavy hydrogen; Or, it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or one or more adjacent pairs are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • R5 is hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, wherein at least one adjacent pair is bonded to each other and substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. Forms a hydrocarbon ring.
  • R5 is hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, wherein at least one adjacent pair is bonded to each other and is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms. Forms a hydrocarbon ring.
  • R5 is hydrogen; heavy hydrogen; or a phenyl group, or one or more adjacent pairs are bonded to benzene; Alternatively, it forms a substituted or unsubstituted indene with a straight-chain or branched alkyl group having 1 to 30 carbon atoms.
  • R5 is hydrogen; heavy hydrogen; or a phenyl group, or one or more adjacent pairs are bonded to benzene; Alternatively, it forms a substituted or unsubstituted indene with a straight-chain or branched alkyl group having 1 to 20 carbon atoms.
  • R5 is hydrogen; heavy hydrogen; or a phenyl group, or one or more adjacent pairs are bonded to benzene; Or, it forms indene substituted or unsubstituted with a methyl group.
  • Ar1 is hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted monocyclic aryl group having 6 to 30 carbon atoms.
  • Ar1 is hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted monocyclic aryl group having 6 to 20 carbon atoms.
  • Ar1 is hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted monocyclic aryl group having 6 to 12 carbon atoms.
  • Ar1 is hydrogen; heavy hydrogen; Or it is a monocyclic aryl group having 6 to 30 carbon atoms.
  • Ar1 is hydrogen; heavy hydrogen; Or it is a monocyclic aryl group having 6 to 20 carbon atoms.
  • Ar1 is hydrogen; heavy hydrogen; Or it is a monocyclic aryl group having 6 to 12 carbon atoms.
  • Ar1 is hydrogen; heavy hydrogen; Or it is a phenyl group.
  • At least one adjacent pair of R6 to R8 is bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, and R6 to The remainders where at least one adjacent pair of R8 is not combined to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms are the same or different, and are each independently hydrogen; Or deuterium.
  • At least one adjacent pair of R6 to R8 is bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the R6 to R8 The remainders where at least one adjacent pair of R8 is not combined to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms are the same or different, and are each independently hydrogen; Or deuterium.
  • At least one adjacent pair of R6 to R8 is bonded to each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, and at least one of R6 to R8
  • the remainders in which one or more adjacent pairs do not combine to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms are the same or different, and are each independently hydrogen; Or deuterium.
  • At least one adjacent pair of R6 to R8 is bonded to each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, and at least one of R6 to R8
  • the remainders in which one or more adjacent pairs do not combine to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms are the same or different, and are each independently hydrogen; Or deuterium.
  • one or more adjacent pairs of at least one of R6 to R8 combine with each other to form benzene, and one or more adjacent pairs of at least one of R6 to R8 combine to form benzene.
  • the remainders that do not form are the same or different from each other, and are each independently hydrogen; Or deuterium.
  • r6 is 2 to 4, and one or more adjacent pairs of R6 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, and the remainder is hydrogen; Or deuterium.
  • r6 is 2 to 4, and any one or more adjacent pairs of R6 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the remainder is hydrogen; Or deuterium.
  • r6 is 2 to 4, any one or more adjacent pairs of R6 are combined with each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, and the remainder is hydrogen; Or deuterium.
  • r6 is 2 to 4, any one or more adjacent pairs of R6 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the remainder is hydrogen; Or deuterium.
  • r6 is 2 to 4, any one or more adjacent pairs of R6 are combined with each other to form benzene, and the remainder is hydrogen; Or deuterium.
  • r7 is 2 to 4, and one or more adjacent pairs of R7 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, and the remainder is hydrogen; Or deuterium.
  • r7 is 2 to 4, and one or more adjacent pairs of R7 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the remainder is hydrogen; Or deuterium.
  • r7 is 2 to 4, and one or more adjacent pairs of R7 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, and the remainder is hydrogen; Or deuterium.
  • r7 is 2 to 4, any one or more adjacent pairs of R7 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the remainder is hydrogen; Or deuterium.
  • r7 is 2 to 4, any one or more adjacent pairs of R7 are combined with each other to form benzene, and the remainder is hydrogen; Or deuterium.
  • r8 is 2 to 5, and any one or more adjacent pairs of R8 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, and the remainder is hydrogen; Or deuterium.
  • r8 is 2 to 5, and any one or more adjacent pairs of R8 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the remainder is hydrogen; Or deuterium.
  • r8 is 2 to 5, any one or more adjacent pairs of R8 are combined with each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, and the remainder is hydrogen; Or deuterium.
  • r8 is 2 to 5, any one or more adjacent pairs of R8 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the remainder is hydrogen; Or deuterium.
  • r8 is 2 to 5, any one or more adjacent pairs of R8 are combined with each other to form benzene, and the remainder is hydrogen; Or deuterium.
  • r'6 is 2 to 4, and any one or more adjacent pairs of R'6 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, the remainder is hydrogen; Or deuterium.
  • r'6 is 2 to 4, and any one or more adjacent pairs of R'6 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms, the remainder is hydrogen; Or deuterium.
  • r'6 is 2 to 4, any one or more adjacent pairs of R'6 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, and the remainder is hydrogen; Or deuterium.
  • r'6 is 2 to 4, and any one or more adjacent pairs of R'6 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the remainder is hydrogen; Or deuterium.
  • r'6 is 2 to 4, any one or more adjacent pairs of R'6 are combined with each other to form benzene, and the remainder is hydrogen; Or deuterium.
  • r'7 is 2 to 4, and any one or more adjacent pairs of R'7 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, the remainder is hydrogen; Or deuterium.
  • r'7 is 2 to 4, and any one or more adjacent pairs of R'7 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms, the remainder is hydrogen; Or deuterium.
  • r'7 is 2 to 4, any one or more adjacent pairs of R'7 are combined with each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, and the remainder is hydrogen; Or deuterium.
  • r'7 is 2 to 4, any one or more adjacent pairs of R'7 are combined with each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the remainder is hydrogen; Or deuterium.
  • r'7 is 2 to 4, any one or more adjacent pairs of R'7 are combined with each other to form benzene, and the remainder is hydrogen; Or deuterium.
  • r'8 is 2 to 5, and any one or more adjacent pairs of R'8 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, the remainder is hydrogen; Or deuterium.
  • r'8 is 2 to 5, and any one or more adjacent pairs of R'8 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms, the remainder is hydrogen; Or deuterium.
  • r'8 is 2 to 5, any one or more adjacent pairs of R'8 are combined with each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, and the remainder is hydrogen; Or it is deuterium.
  • r'8 is 2 to 5, any one or more adjacent pairs of R'8 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the remainder is hydrogen; Or deuterium.
  • r'8 is 2 to 5, any one or more adjacent pairs of R'8 are combined with each other to form benzene, and the remainder is hydrogen; Or deuterium.
  • Formula 1 is any one selected from the following compounds.
  • the present specification provides an organic light-emitting device containing the above-mentioned compound.
  • the 'layer' is interchangeable with the 'film' mainly used in the present technical field, and refers to a coating that covers the target area.
  • the size of the 'layer' is not limited, and each 'layer' may be the same or different in size. According to one embodiment, the size of a 'layer' may be the same as the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.
  • the inclusion of a specific material A in the layer B means that i) one or more types of material A are included in one layer B, and ii) the layer B consists of one or more layers, and the material A is included in a multi-layer B. Includes everything on the first or higher floors.
  • a specific material A is included in the C layer or D layer means that it is i) included in one or more layers of one or more layers of C, ii) included in one or more layers of one or more layers of D, or iii ) This means that it is included in each of the C floors above the first floor and the D floors above the first floor.
  • This specification includes: a first electrode; second electrode; and an organic light emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound of Formula 1.
  • the organic material layer of the organic light emitting device of the present specification may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked.
  • it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc.
  • the structure of the organic light emitting device is not limited to this and may include fewer organic layers.
  • the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the compound.
  • the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound.
  • the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer.
  • the organic material layer includes a light-emitting layer.
  • the organic material layer includes a hole blocking layer.
  • the organic light emitting device is a group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer. It further includes one or more floors selected from.
  • the organic light emitting device includes a first electrode; a second electrode provided opposite to the first electrode; a light emitting layer provided between the first electrode and the second electrode; and two or more organic material layers provided between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.
  • the two or more organic material layers are composed of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer. Two or more may be selected from the group.
  • a hole transport layer of two or more layers is included between the light emitting layer and the first electrode.
  • the two or more hole transport layers may include the same or different materials.
  • the first electrode is an anode or a cathode.
  • the second electrode is a cathode or anode.
  • the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 illustrate an organic light emitting device and are not limited thereto.
  • Figure 1 illustrates the structure of an organic light-emitting device in which a first electrode 2, an organic material layer 4, and a second electrode 3 are sequentially stacked on a substrate 1.
  • the compound is included in the organic layer.
  • FIG. 2 shows a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 8, a hole blocking layer 9, an electron injection layer, and
  • the structure of an organic light emitting device in which the transport layer 10 and the second electrode 3 are sequentially stacked is illustrated.
  • the compound is included in the hole injection layer (5), the hole transport layer (6), or the electron blocking layer (7).
  • the organic light emitting device of the present specification is made of materials and methods known in the art, except that the hole injection layer, hole transport layer, hole injection and transport layer, or electron blocking layer includes the above compound, that is, the compound of Formula 1 above. can be manufactured.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation
  • a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
  • It can be manufactured by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound of Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device.
  • the solution application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.
  • an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the manufacturing method is not limited to this.
  • the substrate may be a first electrode or a second electrode.
  • the anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer.
  • metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO 2 : A combination of a metal such as Sb and an oxide; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited thereto.
  • the cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer.
  • metals or alloys thereof for example magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; Examples include, but are not limited to, multi-layered materials such as LiF/Al or LiO 2 /Al.
  • the light emitting layer may include a host material and a dopant material.
  • Host materials include condensed aromatic ring derivatives or heterocyclic ring-containing compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, These include, but are not limited to, pyrimidine derivatives.
  • the host includes, but is not limited to, a compound represented by the following formula H-1.
  • L20 and L21 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • Ar20 and Ar21 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • R201 is hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • r201 is an integer from 1 to 8, and when r201 is 2 or more, 2 or more R201 are the same or different from each other.
  • L20 and L21 are the same or different from each other and are each independently directly bonded; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or it is a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.
  • L20 and L21 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; A biphenylylene group substituted or unsubstituted with deuterium; Naphthylene group substituted or unsubstituted with deuterium; divalent dibenzofuran group; Or it is a divalent dibenzothiophene group.
  • Ar20 and Ar21 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
  • Ar20 and Ar21 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic to 4-ring heterocyclic group having 6 to 20 carbon atoms.
  • Ar20 and Ar21 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A biphenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Dibenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Naphthobenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Dibenzothiophene group substituted or unsubstituted with a monocyclic
  • Ar20 and Ar21 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Terphenyl group; Naphthyl group substituted or unsubstituted with deuterium; phenanthrene group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or it is a naphthobenzothiophene group.
  • Ar20 is a substituted or unsubstituted heterocyclic group
  • Ar21 is a substituted or unsubstituted aryl group.
  • Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group.
  • R201 is hydrogen; Or it is a phenyl group.
  • the formula H-1 is represented by the following compound.
  • the dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group, and include pyrene, anthracene, chrysene, periplanthene, etc. having an arylamine group.
  • a styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. The substituent is substituted or unsubstituted.
  • styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto.
  • metal complexes include, but are not limited to, iridium complexes and platinum complexes.
  • the dopant material includes, but is not limited to, a compound of the following formula D-1.
  • L101 and L102 are the same or different from each other and are each independently directly bonded; Or a substituted or unsubstituted arylene group,
  • Ar101 to Ar104 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • L101 and L102 are a direct bond.
  • Ar101 to Ar104 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • Ar101 to Ar104 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl having 6 to 30 carbon atoms that is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. energy; Or it is a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • Ar101 to Ar104 are the same as or different from each other, and are each independently a phenyl group; A phenyl group substituted with a methyl group; Or it is a dibenzofuran group.
  • Formula D-1 may be the following compound, but is not limited thereto.
  • the hole injection layer is a layer that receives holes from the electrode.
  • the hole injection material preferably has the ability to transport holes and has an excellent hole receiving effect from the anode and an excellent hole injection effect to the light emitting layer or light emitting material. Additionally, a material that has an excellent ability to prevent the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material is desirable. Additionally, materials with excellent thin film forming ability are desirable. Additionally, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer.
  • HOMO highest occupied molecular orbital
  • hole injection materials include metal porphyrin, oligothiophene, and arylamine-based organic materials; Hexanitrilehexaazatriphenylene series organic substances; Organic substances of the quinacridone series; Perylene-based organic substances; These include, but are not limited to, polythiophene-based conductive polymers such as anthraquinone and polyaniline.
  • the hole injection layer includes, but is not limited to, a compound of the following formula HI-1.
  • At least one of X'1 to X'6 is N, and the remainder is CH,
  • R309 to R314 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heteroaryl group, or it combines with adjacent groups to form a substituted or unsubstituted ring.
  • X'1 to X'6 are N.
  • R309 to R314 are cyano groups.
  • the formula HI-1 may be the following compound, but is not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer.
  • the hole transport material is a hole transport material that receives holes from the anode or hole injection layer and transfers them to the light emitting layer.
  • a material with high mobility for holes is preferred. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions.
  • the hole transport layer includes a compound represented by the following formula HT-1, but is not limited thereto.
  • L501 and L502 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R501 and Ar501 to Ar504 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • L501 and L502 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L501 and L502 are phenylene groups.
  • R501 and Ar501 to Ar504 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R501 and Ar501 to Ar504 are phenyl groups; Or it is a naphthyl group.
  • the formula HT-1 is represented by the following compound.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer.
  • the electron transport material is a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons is preferred. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq 3 ; organic radical compounds; These include, but are not limited to, hydroxyflavone-metal complexes.
  • the electron transport layer can be used with any desired cathode material, as used according to the prior art.
  • suitable cathode materials are conventional materials with a low work function followed by an aluminum or silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, and in each case, an aluminum layer or a silver layer follows.
  • the electron injection layer is a layer that receives electrons from the electrode. It is preferable that the electron injection material has an excellent ability to transport electrons, has an excellent electron receiving effect from the second electrode, and has an excellent electron injection effect with respect to the light emitting layer or light emitting material. In addition, a material that prevents excitons generated in the light-emitting layer from moving to the hole injection layer and has excellent thin film forming ability is desirable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, These include, but are not limited to, metal complex compounds and nitrogen-containing five-membered ring derivatives.
  • the metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, and bis(8-hydroxyquinolinato)manganese. , tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h) ]Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) There are (o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato) gallium. , but is not limited to this.
  • the electron injection and transport layer is a layer that transports electrons to the light-emitting layer.
  • the electron injection and transport layer may use materials exemplified for the electron transport layer and electron injection layer, but is not limited thereto.
  • the electron injection and transport layer includes a compound represented by the following formula ET-1, but is not limited thereto.
  • At least one of Z11 to Z13 is N, the others are CH,
  • At least one of Z21 to Z23 is N, the others are CH,
  • L601 and L602 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar601 to Ar604 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • L601 and L602 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L601 and L602 are phenylene groups.
  • Ar601 to Ar604 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Ar601 to Ar604 are phenyl groups.
  • the chemical formula ET-1 may be the following compound, but is not limited thereto.
  • the electron blocking layer is a layer that can improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer.
  • the organic light emitting device according to an embodiment of the present specification includes an additional electron blocking layer other than the electron blocking layer containing Formula 1, known materials can be used without limitation, and the hole injection layer or the hole transport layer The materials exemplified in the description may be used, but are not limited thereto.
  • the electron blocking layer may be formed between a light-emitting layer and a hole transport layer, between a light-emitting layer and a hole injection layer, or between a light-emitting layer and a layer that simultaneously performs hole injection and hole transport.
  • the hole blocking layer is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc. are included, but are not limited thereto.
  • the hole blocking layer is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc. are included, but are not limited thereto.
  • the hole blocking layer includes a compound represented by the following formula HB-1, but is not limited thereto.
  • At least one of Z31 to Z33 is N, and the remainder is CH,
  • L603 is directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R601 to R603 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Ar605 and Ar606 are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heteroaryl group, or forms a ring by combining with adjacent groups,
  • l603 is an integer from 1 to 3, and when l603 is 2 or more, the 2 or more L603 are the same or different from each other,
  • r601 is an integer from 1 to 4, and when r601 is 2 or more, the 2 or more R601 are the same or different from each other,
  • r602 is an integer from 1 to 4, and when r602 is 2 or more, the 2 or more R602 are the same or different from each other,
  • r603 is an integer of 1 to 3, and when r603 is 2 or more, the 2 or more R603s are the same or different from each other.
  • Z31 to Z33 are N.
  • L603 is a direct bond; Or it is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L603 is a direct bond; phenylene group; naphthylene group; Or it is a biphenylylene group.
  • L603 is a phenylene group; Or it is a naphthylene group.
  • l603 is 2.
  • R601 to R603 are hydrogen.
  • Ar605 and Ar606 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • Ar605 and Ar606 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. am.
  • Ar605 and Ar606 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a biphenyl group.
  • Ar605 and Ar606 are the same as or different from each other, and are each independently a phenyl group or a phenyl group substituted or unsubstituted by a naphthyl group; Or it is a biphenyl group.
  • Ar605 and Ar606 are biphenyl groups.
  • Ar605 and Ar606 are phenyl groups.
  • the chemical formula HB-1 may be the following compound, but is not limited thereto.
  • the organic light emitting device may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
  • the organic light emitting device can be included and used in various electronic devices.
  • the electronic device may be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.
  • a glass substrate coated with a thin film of ITO (Indium Tin Oxide) with a thickness of 1,400 ⁇ was placed in distilled water with a detergent dissolved in it and washed ultrasonically.
  • a detergent manufactured by Fischer Co. was used, and distilled water filtered secondarily using a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was repeated twice with distilled water for 10 minutes.
  • the following compound HAT was thermally vacuum deposited to a thickness of 100 ⁇ to form a hole injection layer.
  • the following compound HT1 was vacuum deposited to a thickness of 1150 ⁇ as a hole transport layer thereon, and then Compound 1 prepared in Synthesis Example 1 was thermally vacuum deposited to a thickness of 150 ⁇ as an electron blocking layer.
  • the following compound BH and the following compound BD were vacuum deposited to a thickness of 200 ⁇ at a weight ratio of 25:1 as an emitting layer.
  • the following compound HB1 was vacuum deposited to a thickness of 50 ⁇ as a hole blocking layer.
  • the following compound ET1 and the following compound LiQ were thermally vacuum deposited to a thickness of 310 ⁇ at a weight ratio of 1:1.
  • Lithium fluoride (LiF) to a thickness of 12 ⁇ and aluminum to a thickness of 1000 ⁇ were sequentially deposited on the electron injection and transport layer to form a cathode, thereby manufacturing an organic light-emitting device.
  • Experimental Examples 1-2 to 1-32 and Comparative Experimental Example 1-1 were conducted in the same manner as Experimental Example 1-1, except that the compounds listed in Table 1 below were used instead of Compound 1 in Experimental Example 1-1.
  • the organic light emitting devices of 1-3 to 1 were manufactured.
  • Experimental Example 1-1 except that the compound EB1 was used as the electron blocking layer instead of the compound 1, and the compound shown in Table 2 below was used as the hole transport layer instead of the compound HT1.
  • the organic light-emitting devices of Experimental Examples 2-1 to 2-14 and Comparative Experimental Examples 2-1 to 2-3 were manufactured in the same manner.
  • the compound of Formula 1 according to an exemplary embodiment of the present specification has excellent electron blocking ability or hole transport ability, and an organic light emitting device using it as an electron blocking layer or hole transport layer has a driving voltage and efficiency. It was confirmed to have a significant effect in terms of lifespan and longevity.
  • the compound of Formula 1 has a structure in which carbazole is substituted in the ortho position on the benzene ring, and is more effective in conjugation than the structure in which carbazole is substituted in the meta or para position. Since it is in a broken state and has a substituent other than hydrogen at the R4 position, it is a structure that makes it easy to control the HOMO and LUMO levels by adjusting the conjugation length.
  • Experimental Examples 1-1 to 1-32 and 2-1 to 2-14 which are organic light-emitting devices using the compound of Formula 1 according to an embodiment of the present specification, are obtained by applying the compound in which the R4 position of Formula 1 of the present specification is hydrogen. It was confirmed that the organic light emitting device showed a significant effect in terms of driving voltage, efficiency, and lifespan compared to Comparative Experimental Examples 1-1 to 1-3 and 2-1 to 2-3.

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Abstract

The present specification relates to a compound of chemical formula 1 and an organic light-emitting device comprising same.

Description

화합물 및 이를 포함하는 유기 발광 소자Compounds and organic light-emitting devices containing them
본 출원은 2022년 7월 14일에 한국특허청에 제출된 한국 특허 출원 제 10-2022-0086757호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of Korean Patent Application No. 10-2022-0086757, filed with the Korea Intellectual Property Office on July 14, 2022, the entire contents of which are incorporated herein by reference.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.This specification relates to compounds and organic light-emitting devices containing the same.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어 질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them. Here, the organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton is When it falls back to the ground state, it glows.
상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다.The development of new materials for organic light-emitting devices as described above continues to be required.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자를 제공한다.This specification provides a compound and an organic light-emitting device containing the same.
본 명세서의 일 실시상태는 하기 화학식 1의 화합물을 제공한다.An exemplary embodiment of the present specification provides a compound of Formula 1 below.
[화학식 1][Formula 1]
Figure PCTKR2023004877-appb-img-000001
Figure PCTKR2023004877-appb-img-000001
상기 화학식 1에 있어서,In Formula 1,
Ar1은 수소; 중수소; 또는 치환 또는 비치환된 단환의 아릴기이고,Ar1 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted monocyclic aryl group,
R1 내지 R3 및 R5는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 어느 한쌍 이상은 서로 결합하여 치환 또는 비치환된 고리를 형성하며,R1 to R3 and R5 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or one or more adjacent pairs are combined with each other to form a substituted or unsubstituted ring,
R4는 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 어느 한쌍 이상은 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R4 is deuterium; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or one or more adjacent pairs are bonded to each other to form a substituted or unsubstituted ring,
R6 내지 R8 중 적어도 하나의 인접한 어느 한 쌍 이상이 서로 결합하여 치환 또는 비치환된 방향족 탄화수소고리를 형성하고, 상기 R6 내지 R8 중 적어도 하나의 인접한 어느 한 쌍 이상이 서로 결합하여 치환 또는 비치환된 방향족 탄화수소고리를 형성하지 않는 나머지는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,At least one adjacent pair of at least one of R6 to R8 is bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring, and at least one adjacent pair of at least one of R6 to R8 is bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring. The remainders that do not form an aromatic hydrocarbon ring are the same or different, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r1 내지 r7은 각각 1 내지 4의 정수이고,r1 to r7 are each integers from 1 to 4,
r8은 1 내지 5의 정수이며,r8 is an integer from 1 to 5,
상기 r6 내지 r8 중 적어도 하나는 2 이상이며,At least one of r6 to r8 is 2 or more,
상기 r1이 2 이상인 경우, 상기 2 이상의 R1은 서로 같거나 상이하며,When r1 is 2 or more, the 2 or more R1 are the same or different from each other,
상기 r2가 2 이상인 경우, 상기 2 이상의 R2는 서로 같거나 상이하고,When r2 is 2 or more, R2 of 2 or more is the same or different from each other,
상기 r3가 2 이상인 경우, 상기 2 이상의 R3는 서로 같거나 상이하며,When r3 is 2 or more, the 2 or more R3s are the same or different from each other,
상기 r4가 2 이상인 경우, 상기 2 이상의 R4는 서로 같거나 상이하고,When r4 is 2 or more, the 2 or more R4 are the same or different from each other,
상기 r5가 2 이상인 경우, 상기 2 이상의 R5는 서로 같거나 상이하며,When r5 is 2 or more, the 2 or more R5 are the same or different from each other,
상기 r6가 2 이상인 경우, 상기 2 이상의 R6는 서로 같거나 상이하고,When r6 is 2 or more, the 2 or more R6 are the same or different from each other,
상기 r7가 2 이상인 경우, 상기 2 이상의 R7는 서로 같거나 상이하며,When r7 is 2 or more, the 2 or more R7 are the same or different from each other,
상기 r8가 2 이상인 경우, 상기 2 이상의 R8는 서로 같거나 상이하다.When r8 is 2 or more, the 2 or more R8s are the same or different from each other.
또한, 본 명세서는 제1 전극; 제2 전극; 및 상기 제1 전극과 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화합물을 포함하는 것인 유기 발광 소자를 제공한다.Additionally, the present specification includes a first electrode; second electrode; and an organic light emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer contains the compound.
본 명세서에 기재된 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있다. 본 명세서의 적어도 하나의 실시상태에 따른 화합물은 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다. 특히, 본 명세서에 기재된 화합물은 정공주입, 정공수송, 정공주입과 정공수송, 전자차단, 발광, 정공차단, 전자수송, 또는 전자주입 재료로 사용될 수 있다. 또한, 기존 유기 발광 소자에 비하여, 낮은 구동전압, 고효율 및/또는 장수명의 효과가 있다.The compounds described in this specification can be used as a material for the organic layer of an organic light-emitting device. A compound according to at least one embodiment of the present specification may improve efficiency, low driving voltage, and/or lifespan characteristics in an organic light-emitting device. In particular, the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection materials. Additionally, compared to existing organic light emitting devices, they have the effects of low driving voltage, high efficiency, and/or long lifespan.
도 1 및 2는 본 명세서의 일 실시상태에 따른 유기 발광 소자의 예를 도시한 것이다.1 and 2 show examples of organic light-emitting devices according to an exemplary embodiment of the present specification.
[부호의 설명][Explanation of symbols]
1: 기판1: substrate
2: 제1 전극2: first electrode
3: 제2 전극3: second electrode
4: 유기물층4: Organic layer
5: 정공주입층5: Hole injection layer
6: 정공수송층6: Hole transport layer
7: 전자차단층7: Electronic blocking layer
8: 발광층8: Light-emitting layer
9: 정공차단층9: Hole blocking layer
10: 전자주입 및 수송층10: Electron injection and transport layer
이하, 본 명세서에 대하여 더욱 상세하게 설명한다.Hereinafter, this specification will be described in more detail.
본 명세서는 상기 화학식 1의 화합물을 제공한다.This specification provides a compound of Formula 1 above.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 화합물은 벤젠고리에 카바졸이 오쏘(ortho) 위치로 치환되는 구조로써, 메타(meta)나 파라(para) 위치로 치환되는 구조보다 컨쥬게이션이 끊어져 있는 상태이므로 밴드갭이 커서 치환기의 종류에 따라 HOMO 및 LUMO 값을 상대적으로 조절하기 쉬운 구조이다. 또한, R4 위치에 수소 이외의 치환기를 가지므로, 컨쥬게이션 길이를 조절함으로써 HOMO 및 LUMO 레벨을 조절하기 쉬운 구조이다. 따라서, 상기 화학식 1의 화합물을 포함하는 유기 발광 소자는 구동전압을 낮고, 효율이 우수하며, 장수명의 특징이 있다.According to an exemplary embodiment of the present specification, the compound of Formula 1 has a structure in which carbazole is substituted in the ortho position on the benzene ring, and conjugation is better than the structure in which carbazole is substituted in the meta or para position. Because it is in a broken state, the band gap is large, making it relatively easy to control the HOMO and LUMO values depending on the type of substituent. In addition, since it has a substituent other than hydrogen at the R4 position, it is a structure in which it is easy to control the HOMO and LUMO levels by adjusting the conjugation length. Therefore, the organic light-emitting device containing the compound of Formula 1 has the characteristics of low driving voltage, excellent efficiency, and long lifespan.
본원 명세서 전체에서, 마쿠시 형식의 표현에 포함된 "이들의 조합"의 용어는 마쿠시 형식의 표현에 기재된 구성 요소들로 이루어진 군에서 선택되는 하나 이상의 혼합 또는 조합을 의미하는 것으로서, 상기 구성 요소들로 이루어진 군에서 선택되는 하나 이상을 포함하는 것을 의미한다.Throughout this specification, the term "combination thereof" included in the Markushi format expression means a mixture or combination of one or more components selected from the group consisting of the components described in the Markushi format expression, It means including one or more selected from the group consisting of.
본 명세서에서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Examples of substituents in this specification are described below, but are not limited thereto.
본 명세서에 있어서,
Figure PCTKR2023004877-appb-img-000002
는 연결되는 부위를 의미한다.In this specification,
Figure PCTKR2023004877-appb-img-000002
means the connected part.
상기 "치환"이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 같거나 상이할 수 있다.The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent. The position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 시아노기; 알킬기; 시클로알킬기; 알콕시기; 알케닐기; 할로알킬기; 실릴기; 붕소기; 아민기; 아릴기; 방향족 탄화수소고리 및 지방족 탄화수소고리의 축합고리기; 및 헤테로아릴기로 이루어진 군으로부터 선택되는 1 이상의 치환기로 치환되었거나, 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다.As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Cyano group; Alkyl group; Cycloalkyl group; Alkoxy group; alkenyl group; Haloalkyl group; silyl group; boron group; Amine group; Aryl group; Condensed ring groups of aromatic hydrocarbon rings and aliphatic hydrocarbon rings; It means that it is substituted with one or more substituents selected from the group consisting of a heteroaryl group, is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituents.
본 명세서에 있어서, 2 이상의 치환기가 연결된다는 것은 어느 하나의 치환기의 수소가 다른 치환기와 연결된 것을 말한다. 예컨대, 2개의 치환기가 연결되는 것은 페닐기와 나프틸기가 연결되어
Figure PCTKR2023004877-appb-img-000003
또는
Figure PCTKR2023004877-appb-img-000004
의 치환기가 될 수 있다. 또한, 3개의 치환기가 연결되는 것은 (치환기 1)-(치환기 2)-(치환기 3)이 연속하여 연결되는 것뿐만 아니라, (치환기 1)에 (치환기 2) 및 (치환기 3)이 연결되는 것도 포함한다. 예컨대, 페닐기, 나프틸기 및 이소프로필기가 연결되어
Figure PCTKR2023004877-appb-img-000005
,
Figure PCTKR2023004877-appb-img-000006
, 또는
Figure PCTKR2023004877-appb-img-000007
의 치환기가 될 수 있다. 4 이상의 치환기가 연결되는 것에도 전술한 정의가 동일하게 적용된다.In this specification, linking two or more substituents means that the hydrogen of one substituent is linked to another substituent. For example, when two substituents are connected, a phenyl group and a naphthyl group are connected.
Figure PCTKR2023004877-appb-img-000003
or
Figure PCTKR2023004877-appb-img-000004
It can be a substituent of . In addition, connecting three substituents not only means that (substituent 1) - (substituent 2) - (substituent 3) are connected in succession, but also (substituent 2) and (substituent 3) are connected to (substituent 1). Includes. For example, phenyl group, naphthyl group and isopropyl group are connected
Figure PCTKR2023004877-appb-img-000005
,
Figure PCTKR2023004877-appb-img-000006
, or
Figure PCTKR2023004877-appb-img-000007
It can be a substituent of . The above definition equally applies to those in which 4 or more substituents are connected.
본 명세서에 있어서, 상기 할로겐기의 예로는 불소, 염소, 브롬 또는 요오드가 있다.In this specification, examples of the halogen group include fluorine, chlorine, bromine, or iodine.
본 명세서에 있어서, 상기 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 30인 것이 바람직하다. 구체적인 예로는 메틸기, 에틸기, 프로필기, n-프로필기, 이소프로필기, 부틸기, n-부틸기, 이소부틸기, tert-부틸기, sec-부틸기, 1-메틸-부틸기, 1-에틸-부틸기, 펜틸기, n-펜틸기, 이소펜틸기, 네오펜틸기, tert-펜틸기, 헥실기, n-헥실기, 1-메틸펜틸기, 2-메틸펜틸기, 4-메틸-2-펜틸기, 3,3-디메틸부틸기, 2-에틸부틸기, 헵틸기, n-헵틸기, 1-메틸헥실기, 시클로펜틸메틸기, 시클로헥실메틸기, 옥틸기, n-옥틸기, tert-옥틸기, 1-메틸헵틸기, 2-에틸헥실기, 2-프로필펜틸기, n-노닐기, 2,2-디메틸헵틸기, 1-에틸-프로필기, 1,1-디메틸-프로필기, 이소헥실기, 4-메틸헥실기, 5-메틸헥실기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, sec-butyl group, 1-methyl-butyl group, 1- Ethyl-butyl group, pentyl group, n-pentyl group, isopentyl group, neopentyl group, tert-pentyl group, hexyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 4-methyl- 2-pentyl group, 3,3-dimethylbutyl group, 2-ethylbutyl group, heptyl group, n-heptyl group, 1-methylhexyl group, cyclopentylmethyl group, cyclohexylmethyl group, octyl group, n-octyl group, tert -Octyl group, 1-methylheptyl group, 2-ethylhexyl group, 2-propylpentyl group, n-nonyl group, 2,2-dimethylheptyl group, 1-ethyl-propyl group, 1,1-dimethyl-propyl group , isohexyl group, 4-methylhexyl group, 5-methylhexyl group, etc., but is not limited thereto.
본 명세서에 있어서, 상기 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 30인 것이 바람직하며, 구체적으로 시클로프로필기, 시클로부틸기, 시클로펜틸기, 3-메틸시클로펜틸기, 2,3-디메틸시클로펜틸기, 시클로헥실기, 3-메틸시클로헥실기, 4-메틸시클로헥실기, 2,3-디메틸시클로헥실기, 3,4,5-트리메틸시클로헥실기, 4-tert-부틸시클로헥실기, 시클로헵틸기, 시클로옥틸기, 아다만틸기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 30 carbon atoms, and specifically includes cyclopropyl group, cyclobutyl group, cyclopentyl group, 3-methylcyclopentyl group, and 2,3-dimethylcyclo group. Pentyl group, cyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 2,3-dimethylcyclohexyl group, 3,4,5-trimethylcyclohexyl group, 4-tert-butylcyclohexyl group, Cycloheptyl group, cyclooctyl group, adamantyl group, etc. are included, but are not limited thereto.
본 명세서에 있어서, 상기 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 30인 것이 바람직하다. 구체적으로, 메톡시기, 에톡시기, n-프로폭시기, 이소프로폭시기, n-부톡시기, 이소부톡시기, tert-부톡시기, sec-부톡시기, n-펜틸옥시기, 네오펜틸옥시기, 이소펜틸옥시기, n-헥실옥시기, 3,3-디메틸부틸옥시기, 2-에틸부틸옥시기, n-옥틸옥시기, n-노닐옥시기, n-데실옥시기, 벤질옥시기, p-메틸벤질옥시기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkoxy group may be straight chain, branched chain, or ring chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, tert-butoxy group, sec-butoxy group, n-pentyloxy group, neopentyloxy group, Isopentyloxy group, n-hexyloxy group, 3,3-dimethylbutyloxy group, 2-ethylbutyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group, benzyloxy group, p -It may be a methylbenzyloxy group, etc., but is not limited thereto.
본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 30인 것이 바람직하다. 구체적인 예로는 비닐기, 1-프로페닐기, 이소프로페닐기, 1-부테닐기, 2-부테닐기, 3-부테닐기, 1-펜테닐기, 2-펜테닐기, 3-펜테닐기, 3-메틸-1-부테닐기, 1,3-부타디에닐기, 알릴기, 1-페닐비닐-1-일기, 2-페닐비닐-1-일기, 2,2-디페닐비닐-1-일기, 2-페닐-2-(나프틸-1-일)비닐-1-일기, 2,2-비스(디페닐-1-일)비닐-1-일기, 스틸베닐기, 스티레닐기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include vinyl group, 1-propenyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 3-methyl-1 -Butenyl group, 1,3-butadienyl group, allyl group, 1-phenylvinyl-1-yl group, 2-phenylvinyl-1-yl group, 2,2-diphenylvinyl-1-yl group, 2-phenyl-2 -(naphthyl-1-yl)vinyl-1-yl group, 2,2-bis(diphenyl-1-yl)vinyl-1-yl group, stilbenyl group, styrenyl group, etc., but is not limited thereto. .
본 명세서에 있어서, 상기 할로알킬기는 상기 알킬기의 정의 중 알킬기의 수소 대신 적어도 하나의 할로겐기가 치환되는 것을 의미한다.In the present specification, the haloalkyl group means that at least one halogen group is substituted for hydrogen in the alkyl group in the definition of the alkyl group.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하며, 상기 아릴기는 단환식 또는 다환식일 수 있다.In the present specification, the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
상기 아릴기가 단환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나, 탄소수 6 내지 30인 것이 바람직하다. 구체적으로 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.When the aryl group is a monocyclic aryl group, the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms. Specifically, the monocyclic aryl group may be a phenyl group, a biphenyl group, or a terphenyl group, but is not limited thereto.
상기 아릴기가 다환식 아릴기인 경우 탄소수는 특별히 한정되지 않으나. 탄소수 10 내지 30인 것이 바람직하다. 구체적으로 다환식 아릴기로는 나프틸기, 안트라센기, 페난트렌기, 트리페닐렌기, 파이렌기, 페날렌기, 페릴렌기, 크라이센기, 플루오렌기 등이 될 수 있으나, 이에 한정되는 것은 아니다. If the aryl group is a polycyclic aryl group, the number of carbon atoms is not particularly limited. It is preferable to have 10 to 30 carbon atoms. Specifically, the polycyclic aryl group may be a naphthyl group, anthracene group, phenanthrene group, triphenylene group, pyrene group, phenalene group, perylene group, chrysene group, fluorene group, etc., but is not limited thereto.
본 명세서에 있어서, 상기 플루오렌기는 치환될 수 있으며, 인접한 기들이 서로 결합하여 고리를 형성할 수 있다. In the present specification, the fluorene group may be substituted, and adjacent groups may combine with each other to form a ring.
상기 플루오렌기의 예시로는
Figure PCTKR2023004877-appb-img-000008
등이 있으나, 이에 한정되지 않는다.Examples of the fluorene group include
Figure PCTKR2023004877-appb-img-000008
etc., but is not limited to this.
본 명세서에 있어서, "인접한" 기는 해당 치환기가 치환된 원자와 직접 연결된 원자에 치환된 치환기, 해당 치환기와 입체구조적으로 가장 가깝게 위치한 치환기, 또는 해당 치환기가 치환된 원자에 치환된 다른 치환기를 의미할 수 있다. 예컨대, 벤젠고리에서 오르토(ortho)위치로 치환된 2개의 치환기 및 지방족 고리에서 동일 탄소에 치환된 2개의 치환기는 서로 "인접한" 기로 해석될 수 있다.As used herein, an “adjacent” group may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the substituent in terms of structure, or another substituent substituted on the atom on which the substituent is substituted. You can. For example, two substituents substituted at ortho positions in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring can be interpreted as “adjacent” groups.
본 명세서에 있어서, 상기 헤테로아릴기는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 30인 것이 바람직하며, 상기 헤테로아릴기는 단환식 또는 다환식일 수 있다. 헤테로아릴기의 예로는 티오펜기, 퓨란기, 피롤기, 이미다졸기, 티아졸기, 옥사졸기, 옥사디아졸기, 피리딘기, 바이피리딘기, 피리미딘기, 트리아진기, 트리아졸기, 아크리딘기, 피리다진기, 피라진기, 퀴놀린기, 퀴나졸린기, 퀴녹살린기, 프탈라진기, 피리도 피리미딘기, 피리도 피라진기, 피라지노 피라진기, 이소퀴놀린기, 인돌기, 카바졸기, 벤즈옥사졸기, 벤즈이미다졸기, 벤조티아졸기, 벤조카바졸기, 벤조티오펜기, 디벤조티오펜기, 벤조퓨란기, 페난트리딘기(phenanthridine), 페난쓰롤린기(phenanthroline), 이소옥사졸기, 티아디아졸기, 디벤조퓨란기, 디벤조실롤기, 페노크산틴기(phenoxathiine), 페녹사진기(phenoxazine), 페노티아진기(phenothiazine), 디하이드로인데노카바졸기, 스피로플루오렌잔텐기 및 스피로플루오렌티옥산텐기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the heteroaryl group includes one or more non-carbon atoms and heteroatoms. Specifically, the heteroaryl group may include one or more atoms selected from the group consisting of O, N, Se, and S. . The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, and acridine group. , pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyrido pyrimidine group, pyrido pyrazine group, pyrazino pyrazine group, isoquinoline group, indole group, carbazole group, benzyl group. Oxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine group, phenanthroline group, isoxazole group, thia Diazole group, dibenzofuran group, dibenzosilol group, phenoxanthine group, phenoxazine group, phenothiazine group, dihydroindenocarbazole group, spirofluorenexanthene group and spirofluorene. Thioxanthene group, etc., but is not limited thereto.
본 명세서 있어서, 상기 실릴기는 알킬실릴기, 아릴실릴기, 헤테로아릴실릴기 등일 수 있다. 상기 알킬실릴기 중 알킬기는 전술한 알킬기의 예시가 적용될 수 있고, 상기 아릴실릴기 중 아릴기는 전술한 아릴기의 예시가 적용될 수 있으며, 상기 헤테로아릴실릴기 중 헤테로아릴기는 상기 헤테로아릴기의 예시가 적용될 수 있다.In the present specification, the silyl group may be an alkylsilyl group, an arylsilyl group, a heteroarylsilyl group, etc. Among the alkylsilyl groups, examples of the alkyl group described above may be applied to the alkyl group, examples of the aryl group described above may be applied to the aryl group among the arylsilyl groups, and examples of the heteroaryl group among the heteroarylsilyl groups may apply to the heteroaryl group. can be applied.
본 명세서에 있어서, 상기 붕소기는 -BR100R101일 수 있으며, 상기 R100 및 R101은 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐; 니트릴기; 치환 또는 비치환된 탄소수 3 내지 30의 단환 또는 다환의 시클로알킬기; 치환 또는 비치환된 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 및 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기로 이루어진 군으로부터 선택될 수 있다. 상기 붕소기는 구체적으로 디메틸붕소기, 디에틸붕소기, t-부틸메틸붕소기, 디페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group may be -BR 100 R 101 , and R 100 and R 101 are the same or different, and are each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; and a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms. The boron group specifically includes, but is not limited to, dimethyl boron group, diethyl boron group, t-butylmethyl boron group, and diphenyl boron group.
본 명세서에 있어서, 상기 아민기는 -NH2, 알킬아민기, N-알킬아릴아민기, 아릴아민기, N-아릴헤테로아릴아민기, N-알킬헤테로아릴아민기, 및 헤테로아릴아민기로 이루어진 군으로부터 선택될 수 있으며, 탄소수는 특별히 한정되지 않으나, 1 내지 30인 것이 바람직하다. 아민기의 구체적인 예로는 메틸아민기, 디메틸아민기, 에틸아민기, 디에틸아민기, 페닐아민기, 나프틸아민기, 바이페닐아민기, 안트라세닐아민기, 9-메틸-안트라세닐아민기, 디페닐아민기, 디톨릴아민기, N-페닐톨릴아민기, N-페닐바이페닐아민기, N-페닐나프틸아민기, N-바이페닐나프틸아민기; N-나프틸플루오레닐아민기, N-페닐페난트레닐아민기, N-바이페닐페난트레닐아민기, N-페닐플루오레닐아민기, N-페닐터페닐아민기, N-페난트레닐플루오레닐아민기, N-바이페닐플루오레닐아민기 등이 있으나, 이에 한정되는 것은 아니다.In the present specification, the amine group is a group consisting of -NH 2 , an alkylamine group, an N-alkylarylamine group, an arylamine group, an N-arylheteroarylamine group, an N-alkylheteroarylamine group, and a heteroarylamine group. It may be selected from, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of amine groups include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group. , diphenylamine group, ditolylamine group, N-phenyltolylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-biphenylnaphthylamine group; N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine group, N-phenanthre Examples include, but are not limited to, a nylfluorenylamine group and an N-biphenylfluorenylamine group.
본 명세서에 있어서, 상기 N-알킬아릴아민기는 아민기의 N에 알킬기 및 아릴기가 치환된 아민기를 의미한다. 상기 N-알킬아릴아민기 중의 알킬기와 아릴기는 전술한 알킬기 및 아릴기의 예시와 같다.In the present specification, the N-alkylarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and an aryl group. The alkyl group and aryl group in the N-alkylarylamine group are the same as the examples of the alkyl group and aryl group described above.
본 명세서에 있어서, 상기 N-아릴헤테로아릴아민기는 아민기의 N에 아릴기 및 헤테로아릴기가 치환된 아민기를 의미한다. 상기 N-아릴헤테로아릴아민기 중의 아릴기와 헤테로아릴기는 전술한 아릴기 및 헤테로아릴기의 예시와 같다.In the present specification, the N-arylheteroarylamine group refers to an amine group in which an aryl group and a heteroaryl group are substituted at the N of the amine group. The aryl group and heteroaryl group in the N-arylheteroarylamine group are the same as the examples of the aryl group and heteroaryl group described above.
본 명세서에 있어서, 상기 N-알킬헤테로아릴아민기는 아민기의 N에 알킬기 및 헤테로아릴기가 치환된 아민기를 의미한다. 상기 N-알킬헤테로아릴아민기 중의 알킬기와 헤테로아릴기는 전술한 알킬기 및 헤테로아릴기의 예시와 같다.In the present specification, the N-alkylheteroarylamine group refers to an amine group in which the N of the amine group is substituted with an alkyl group and a heteroaryl group. The alkyl group and heteroaryl group in the N-alkylheteroarylamine group are the same as the examples of the alkyl group and heteroaryl group described above.
본 명세서에 있어서, 상기 아릴아민기의 예로는 치환 또는 비치환된 모노아릴아민기, 또는 치환 또는 비치환된 디아릴아민기가 있다. 상기 아릴기가 2 이상을 포함하는 아릴아민기는 단환식 아릴기, 다환식 아릴기, 또는 단환식 아릴기와 다환식 아릴기를 동시에 포함할 수 있다. 예컨대, 상기 아릴아민기 중의 아릴기는 전술한 아릴기의 예시 중에서 선택될 수 있다.In the present specification, examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group. The arylamine group containing two or more aryl groups may include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group simultaneously. For example, the aryl group in the arylamine group may be selected from the examples of aryl groups described above.
본 명세서에 있어서, 상기 헤테로아릴아민기의 예로는 치환 또는 비치환된 모노헤테로아릴아민기, 또는 치환 또는 비치환된 디헤테로아릴아민기가 있다. 상기 헤테로아릴기가 2 이상을 포함하는 헤테로아릴아민기는 단환식 헤테로아릴기, 다환식 헤테로아릴기, 또는 단환식 헤테로아릴기와 다환식 헤테로아릴기를 동시에 포함할 수 있다. 예컨대, 상기 헤테로아릴아민기 중의 헤테로아릴기는 전술한 헤테로아릴기의 예시 중에서 선택될 수 있다.In the present specification, examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group. The heteroarylamine group containing two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group simultaneously. For example, the heteroaryl group in the heteroarylamine group may be selected from the examples of heteroaryl groups described above.
본 명세서에 있어서, 상기 탄화수소고리기는 방향족 탄화수소고리기; 지방족 탄화수소고리기; 또는 방향족 탄화수소고리 및 지방족 탄화수소고리의 축합고리기일 수 있으며, 상기 방향족 탄화수소고리기에는 전술한 아릴기에 대한 설명이 적용되고, 지방족 탄화수소고리기에는 전술한 시클로알킬기에 대한 설명이 적용될 수 있다. 또한, 방향족 탄화수소고리 및 지방족 탄화수소고리의 축합고리기는 전술한 아릴기 및 시클로알킬기가 서로 축합된 구조가 적용될 수 있다.In the present specification, the hydrocarbon ring group is an aromatic hydrocarbon ring group; Aliphatic hydrocarbon ring group; Alternatively, it may be a condensed ring group of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring. The description of the aryl group described above may be applied to the aromatic hydrocarbon ring group, and the description of the cycloalkyl group described above may be applied to the aliphatic hydrocarbon ring group. In addition, the condensed ring group of the aromatic hydrocarbon ring and the aliphatic hydrocarbon ring may have a structure in which the above-mentioned aryl group and cycloalkyl group are condensed with each other.
본 명세서에 있어서, " 인접한 어느 한쌍 이상은 서로 결합하여 치환 또는 비치환된 고리를 형성"에서 "인접한"의 의미는 전술한 바와 동일하며, 상기 "고리"는 치환 또는 비치환된 탄화수소고리; 또는 치환 또는 비치환된 헤테로고리를 의미한다.In the present specification, the meaning of "adjacent" in "one or more adjacent pairs combine to form a substituted or unsubstituted ring" is the same as described above, and the "ring" refers to a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocycle.
본 명세서에 있어서, 상기 탄화수소고리는 방향족 탄화수소고리, 지방족 탄화수소고리, 또는 방향족 탄화수소고리와 지방족 탄화수소고리의 축합고리일 수 있으며, 상기 1가가 아닌 것을 제외하고 상기 시클로알킬기, 아릴기, 및 이들의 조합의 예시 중에서 선택될 수 있으며, 상기 탄화수소고리는 벤젠, 시클로헥산, 아다만탄, 바이시클로[2.2.1]헵탄, 바이시클로[2.2.1]옥탄, 테트라하이드로나프탈렌, 테트라하이드로안트라센, 1,2,3,4-테트라하이드로-1,4-메타노나프탈렌, 1,2,3,4-테트라하이드로-1,4-에타노나프탈렌, 스피로시클로펜탄플루오렌, 스피로아다만탄플루오렌, 및 스피로시클로헥산플루오렌 등이 있으나, 이에만 한정되는 것은 아니다.In the present specification, the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, and, except for those that are not monovalent, the cycloalkyl group, the aryl group, and combinations thereof. It can be selected from examples, and the hydrocarbon ring is benzene, cyclohexane, adamantane, bicyclo[2.2.1]heptane, bicyclo[2.2.1]octane, tetrahydronaphthalene, tetrahydroanthracene, 1,2 , 3,4-tetrahydro-1,4-methanonaphthalene, 1,2,3,4-tetrahydro-1,4-ethanonaphthalene, spirocyclopentane fluorene, spiroadamantane fluorene, and spiro Cyclohexane fluorene, etc., but is not limited to this.
본 명세서에 있어서, 상기 헤테로고리는 탄소가 아닌 원자, 이종원자를 1 이상 포함하는 것으로서, 구체적으로 상기 이종 원자는 O, N, Se 및 S 등으로 이루어진 군에서 선택되는 원자를 1 이상 포함할 수 있다. 상기 헤테로고리는 단환 또는 다환일 수 있으며, 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있으며, 상기 방향족 헤테로고리는 1가가 아닌 것을 제외하고 상기 헤테로고리기 중 헤테로아릴기의 예시 중에서 선택될 수 있다.In the present specification, the heterocycle includes one or more non-carbon atoms and heteroatoms. Specifically, the heterocycle may include one or more atoms selected from the group consisting of O, N, Se, and S. . The heterocycle may be monocyclic or polycyclic, and may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and the aromatic heterocycle may be selected from examples of heteroaryl groups among the heterocyclic groups, except that the aromatic heterocycle is not monovalent. there is.
본 명세서에 있어서, 상기 지방족 헤테로고리란 헤테로원자 중 1개 이상을 포함하는 지방족 고리를 의미한다. 또한, 방향족 헤테로고리를 제외한 헤테로고리를 의미하며, 이중결합을 포함하나, 방향족이 아닌 헤테로고리는 지방족 헤테로고리이다. 지방족 헤테로고리의 예로는, 옥시레인(oxirane), 테트라하이드로퓨란, 1,4-디옥세인(1,4-dioxane), 피롤리딘, 피페리딘, 모르폴린(morpholine), 옥세판, 아조케인, 티오케인, 테트라하이드로나프토티오펜, 테트라하이드로나프토퓨란, 테트라하이드로벤조티오펜, 및 테트라하이드로벤조퓨란 등이 있으나, 이에 한정되지 않는다.In the present specification, the aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. In addition, it refers to a heterocycle excluding an aromatic heterocycle, and a heterocycle that contains a double bond but is not aromatic is an aliphatic heterocycle. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, and azocaine. , thiocane, tetrahydronaphthothiophene, tetrahydronaphthofuran, tetrahydrobenzothiophene, and tetrahydrobenzofuran, but are not limited thereto.
본 명세서에 있어서, 상기 지방족 헤테로고리(기)는 헤테로원자 중 1개 이상을 포함하는 지방족 고리(기)를 의미한다. 또한, 방향족 헤테로고리(기)를 제외한 헤테로고리(기)를 의미하며, 이중결합을 포함하나, 방향족이 아닌 헤테로고리(기)는 지방족 헤테로고리(기)이다.In the present specification, the aliphatic heterocycle (group) refers to an aliphatic ring (group) containing one or more heteroatoms. In addition, it refers to a heterocycle (group) excluding an aromatic heterocycle (group), and a heterocycle (group) that contains a double bond but is not aromatic is an aliphatic heterocycle (group).
본 명세서에 있어서, 상기 지방족 또는 방향족과 지방족의 축합 헤테로고리의 예로는 테트라하이드로벤조나프토티오펜 및 테트라하이드로벤조나프토퓨란 등이 있으나, 이에 한정되지 않는다.In the present specification, examples of the aliphatic or aromatic-aliphatic condensed heterocycle include tetrahydrobenzonaphthothiophene and tetrahydrobenzonaphthofuran, but are not limited thereto.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1 중 치환기가 표시되지 않은 부분은 수소, 또는 중수소가 치환된 것을 의미할 수 있다.In an exemplary embodiment of the present specification, the portion in Formula 1 where a substituent is not indicated may mean that hydrogen or deuterium has been substituted.
본 명세서에서 달리 정의되지 않는 한, 본 명세서에서 사용되는 모든 기술적 및 과학적 용어는 본 발명이 속하는 기술 분야의 당업자에 의해 통상적으로 이해되는 바와 동일한 의미를 갖는다. 본 명세서에서 설명되는 것과 유사하거나 등가인 방법 및 재료가 본 발명의 실시 형태의 실시 또는 시험에서 사용될 수 있지만, 적합한 방법 및 재료가 후술된다. 본 명세서에서 언급되는 모든 간행물, 특허 출원, 특허 및 다른 참고 문헌은 전체적으로 본 명세서에 참고로 포함되며, 상충되는 경우 특정 어구(passage)가 언급되지 않으면, 정의를 비롯한 본 명세서가 우선할 것이다. 게다가, 재료, 방법, 및 실시예는 단지 예시적인 것이며 제한하고자 하는 것은 아니다.Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by a person skilled in the art to which the present invention pertains. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety, and in case of conflict, the present specification, including definitions, will control unless a specific passage is mentioned. Moreover, the materials, methods, and examples are illustrative only and are not intended to be limiting.
이하, 상기 화학식 1의 화합물에 관하여 상세히 설명한다.Hereinafter, the compound of Formula 1 will be described in detail.
본 명세서의 일 실시상태에 따르면, 상기 R1은 수소이다.According to an exemplary embodiment of the present specification, R1 is hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소이다.According to an exemplary embodiment of the present specification, R2 is hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 R3는 수소이다.According to an exemplary embodiment of the present specification, R3 is hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 R1은 중수소이다.According to an exemplary embodiment of the present specification, R1 is deuterium.
본 명세서의 일 실시상태에 따르면, 상기 R2는 중수소이다.According to an exemplary embodiment of the present specification, R2 is deuterium.
본 명세서의 일 실시상태에 따르면, 상기 R3는 중수소이다.According to an exemplary embodiment of the present specification, R3 is deuterium.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-1이다.According to an exemplary embodiment of the present specification, Formula 1 is the following Formula 1-1.
[화학식 1-1][Formula 1-1]
Figure PCTKR2023004877-appb-img-000009
Figure PCTKR2023004877-appb-img-000009
상기 화학식 1-1에 있어서,In Formula 1-1,
R2, R4 내지 R8, r2, r4 내지 r8 및 Ar1의 정의는 상기 화학식 1에서 정의한 바와 동일하다.The definitions of R2, R4 to R8, r2, r4 to r8, and Ar1 are the same as those defined in Formula 1 above.
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; 중수소; 또는 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이거나, 인접한 어느 한쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; heavy hydrogen; Or, it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or one or more adjacent pairs are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; 중수소; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기이거나, 인접한 어느 한쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; heavy hydrogen; Or, it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or one or more adjacent pairs are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; 중수소; 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기이거나, 인접한 어느 한쌍 이상은 서로 결합하여 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; heavy hydrogen; Alternatively, it is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or one or more adjacent pairs are bonded to each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기이거나, 인접한 어느 한쌍 이상은 서로 결합하여 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; Alternatively, it is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or one or more adjacent pairs are bonded to each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; 중수소; 또는 페닐기이거나, 인접한 어느 한쌍 이상은 서로 결합하여 벤젠을 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; heavy hydrogen; Or it is a phenyl group, or one or more adjacent pairs combine with each other to form benzene.
본 명세서의 일 실시상태에 따르면, 상기 R2는 수소; 중수소; 또는 페닐기이거나, 인접한 어느 한 쌍이 서로 결합하여 벤젠을 형성한다.According to an exemplary embodiment of the present specification, R2 is hydrogen; heavy hydrogen; Or, it is a phenyl group, or any adjacent pair combines with each other to form benzene.
본 명세서의 일 실시상태에 따르면, 상기 R1는 수소; 중수소; 또는 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이거나, 인접한 어느 한쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; Or, it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or one or more adjacent pairs are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1는 수소; 중수소; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기이거나, 인접한 어느 한쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; Or, it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or one or more adjacent pairs are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1는 수소; 중수소; 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기이거나, 인접한 어느 한쌍 이상은 서로 결합하여 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; Alternatively, it is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or one or more adjacent pairs are bonded to each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1는 수소; 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기이거나, 인접한 어느 한쌍 이상은 서로 결합하여 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R1 is hydrogen; Alternatively, it is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or one or more adjacent pairs are bonded to each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R1는 수소; 중수소; 또는 페닐기이거나, 인접한 어느 한쌍 이상은 서로 결합하여 벤젠을 형성한다.According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; Or it is a phenyl group, or one or more adjacent pairs combine with each other to form benzene.
본 명세서의 일 실시상태에 따르면, 상기 R1는 수소; 중수소; 또는 페닐기이거나, 인접한 어느 한 쌍이 서로 결합하여 벤젠을 형성한다.According to an exemplary embodiment of the present specification, R1 is hydrogen; heavy hydrogen; Or, it is a phenyl group, or any adjacent pair combines with each other to form benzene.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-2 내지 1-5 중 어느 하나이다.According to an exemplary embodiment of the present specification, Formula 1 is any one of the following Formulas 1-2 to 1-5.
[화학식 1-2][Formula 1-2]
Figure PCTKR2023004877-appb-img-000010
Figure PCTKR2023004877-appb-img-000010
[화학식 1-3][Formula 1-3]
Figure PCTKR2023004877-appb-img-000011
Figure PCTKR2023004877-appb-img-000011
[화학식 1-4][Formula 1-4]
Figure PCTKR2023004877-appb-img-000012
Figure PCTKR2023004877-appb-img-000012
[화학식 1-5][Formula 1-5]
Figure PCTKR2023004877-appb-img-000013
Figure PCTKR2023004877-appb-img-000013
상기 화학식 1-2 내지 1-5에 있어서,In Formulas 1-2 to 1-5,
R1, R3 내지 R8, r1, r3 내지 r8 및 Ar1의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of R1, R3 to R8, r1, r3 to r8 and Ar1 are the same as those defined in Formula 1 above,
R'2 및 R21은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,R'2 and R21 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r'2는 1 내지 4의 정수이고,r'2 is an integer from 1 to 4,
r21은 1 내지 6의 정수이며,r21 is an integer from 1 to 6,
상기 r'2가 2 이상인 경우, 상기 2 이상의 R'2는 서로 같거나 상이하고,When r'2 is 2 or more, R'2 of 2 or more is the same as or different from each other,
상기 r21이 2 이상인 경우, 상기 2 이상의 R21은 서로 같거나 상이하다.When r21 is 2 or more, the 2 or more R21s are the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-6 내지 1-9 중 어느 하나이다.According to an exemplary embodiment of the present specification, Formula 1 is any one of the following Formulas 1-6 to 1-9.
[화학식 1-6][Formula 1-6]
Figure PCTKR2023004877-appb-img-000014
Figure PCTKR2023004877-appb-img-000014
[화학식 1-7][Formula 1-7]
Figure PCTKR2023004877-appb-img-000015
Figure PCTKR2023004877-appb-img-000015
[화학식 1-8][Formula 1-8]
Figure PCTKR2023004877-appb-img-000016
Figure PCTKR2023004877-appb-img-000016
[화학식 1-9][Formula 1-9]
Figure PCTKR2023004877-appb-img-000017
Figure PCTKR2023004877-appb-img-000017
상기 화학식 1-6 내지 1-9에 있어서,In Formulas 1-6 to 1-9,
R4 내지 R8, r4 내지 r8 및 Ar1의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of R4 to R8, r4 to r8 and Ar1 are the same as those defined in Formula 1 above,
R'2는 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,R'2 is hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
r'2는 1 내지 4의 정수이고,r'2 is an integer from 1 to 4,
상기 r'2가 2 이상인 경우, 상기 2 이상의 R'2는 서로 같거나 상이하다.When r'2 is 2 or more, R'2 of 2 or more is the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 1-10 내지 1-12 중 어느 하나이다.According to an exemplary embodiment of the present specification, Formula 1 is any one of the following Formulas 1-10 to 1-12.
[화학식 1-10][Formula 1-10]
Figure PCTKR2023004877-appb-img-000018
Figure PCTKR2023004877-appb-img-000018
[화학식 1-11][Formula 1-11]
Figure PCTKR2023004877-appb-img-000019
Figure PCTKR2023004877-appb-img-000019
[화학식 1-12][Formula 1-12]
Figure PCTKR2023004877-appb-img-000020
Figure PCTKR2023004877-appb-img-000020
상기 화학식 1-10 내지 1-12에 있어서,In Formulas 1-10 to 1-12,
R2, r2, R4, r4, R5, r5 및 Ar1의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of R2, r2, R4, r4, R5, r5 and Ar1 are the same as those defined in Formula 1 above,
R'6 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이며,One or more adjacent pairs of R'6 combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring, and the remainder is hydrogen; or deuterium,
R'7 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소 이고,One or more adjacent pairs of R'7 combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring, and the remainder is hydrogen; or deuterium,
R'8 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 방향족 탄화수소고리를 형성하며, 나머지는 수소; 또는 중수소 이며,One or more adjacent pairs of R'8 combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring, and the remainder is hydrogen; or deuterium,
r'6은 2 내지 4의 정수이고, 상기 r'6이 2 이상인 경우, 상기 2 이상의 R'6은 서로 같거나 상이하고, r'6 is an integer of 2 to 4, and when r'6 is 2 or more, R'6 of 2 or more is the same as or different from each other,
r'7은 2 내지 4의 정수이며, 상기 r'7이 2 이상인 경우, 상기 2 이상의 R'7은 서로 같거나 상이하며,r'7 is an integer of 2 to 4, and when r'7 is 2 or more, R'7 of 2 or more is the same as or different from each other,
r'8은 2 내지 5의 정수이고, 상기 r'8이 2 이상인 경우, 상기 2 이상의 R'은 서로 같거나 상이하다.r'8 is an integer of 2 to 5, and when r'8 is 2 or more, R' of 2 or more is the same or different.
본 명세서의 일 실시상태에 따르면, 상기 R4는 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R4 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R4는 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R4 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R4는 치환 또는 비치환된 탄소수 6 내지 10의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R4 is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R4는 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R4 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R4는 탄소수 6 내지 20의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R4 is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R4는 탄소수 6 내지 10의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R4 is a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R4는 페닐기이다.According to an exemplary embodiment of the present specification, R4 is a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 r4는 1이다.According to an exemplary embodiment of the present specification, r4 is 1.
본 명세서의 일 실시상태에 따르면, 상기 R5는 수소; 중수소; 또는 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이거나, 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R5 is hydrogen; heavy hydrogen; Or, it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or one or more adjacent pairs are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R5는 수소; 중수소; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 아릴기이거나, 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R5 is hydrogen; heavy hydrogen; Or, it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or one or more adjacent pairs are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R5는 수소; 중수소; 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기이거나, 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R5 is hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, wherein at least one adjacent pair is bonded to each other and substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. Forms a hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 R5는 수소; 중수소; 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기이거나, 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성한다.According to an exemplary embodiment of the present specification, R5 is hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a monocyclic or polycyclic aromatic group having 6 to 20 carbon atoms, wherein at least one adjacent pair is bonded to each other and is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms. Forms a hydrocarbon ring.
본 명세서의 일 실시상태에 따르면, 상기 R5는 수소; 중수소; 또는 페닐기이거나, 인접한 어느 한 쌍 이상은 서로 결합하여 벤젠; 또는 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 인덴을 형성한다.According to an exemplary embodiment of the present specification, R5 is hydrogen; heavy hydrogen; or a phenyl group, or one or more adjacent pairs are bonded to benzene; Alternatively, it forms a substituted or unsubstituted indene with a straight-chain or branched alkyl group having 1 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R5는 수소; 중수소; 또는 페닐기이거나, 인접한 어느 한 쌍 이상은 서로 결합하여 벤젠; 또는 탄소수 1 내지 20의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 인덴을 형성한다.According to an exemplary embodiment of the present specification, R5 is hydrogen; heavy hydrogen; or a phenyl group, or one or more adjacent pairs are bonded to benzene; Alternatively, it forms a substituted or unsubstituted indene with a straight-chain or branched alkyl group having 1 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R5는 수소; 중수소; 또는 페닐기이거나, 인접한 어느 한 쌍 이상은 서로 결합하여 벤젠; 또는 메틸기로 치환 또는 비치환된 인덴을 형성한다.According to an exemplary embodiment of the present specification, R5 is hydrogen; heavy hydrogen; or a phenyl group, or one or more adjacent pairs are bonded to benzene; Or, it forms indene substituted or unsubstituted with a methyl group.
본 명세서의 일 실시상태에 따르면, 상기 Ar1은 수소; 중수소; 또는 치환 또는 비치환된 탄소수 6 내지 30의 단환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar1 is hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted monocyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1은 수소; 중수소; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar1 is hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted monocyclic aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1은 수소; 중수소; 또는 치환 또는 비치환된 탄소수 6 내지 12의 단환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar1 is hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted monocyclic aryl group having 6 to 12 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1은 수소; 중수소; 또는 탄소수 6 내지 30의 단환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar1 is hydrogen; heavy hydrogen; Or it is a monocyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1은 수소; 중수소; 또는 탄소수 6 내지 20의 단환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar1 is hydrogen; heavy hydrogen; Or it is a monocyclic aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1은 수소; 중수소; 또는 탄소수 6 내지 12의 단환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar1 is hydrogen; heavy hydrogen; Or it is a monocyclic aryl group having 6 to 12 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar1은 수소; 중수소; 또는 페닐기이다.According to an exemplary embodiment of the present specification, Ar1 is hydrogen; heavy hydrogen; Or it is a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 R6 내지 R8 중 적어도 하나의 인접한 어느 한 쌍 이상이 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성하고, 상기 R6 내지 R8 중 적어도 하나의 인접한 어느 한 쌍 이상이 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성하지 않는 나머지는 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, at least one adjacent pair of R6 to R8 is bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, and R6 to The remainders where at least one adjacent pair of R8 is not combined to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms are the same or different, and are each independently hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 R6 내지 R8 중 적어도 하나의 인접한 어느 한 쌍 이상이 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성하고, 상기 R6 내지 R8 중 적어도 하나의 인접한 어느 한 쌍 이상이 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성하지 않는 나머지는 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, at least one adjacent pair of R6 to R8 is bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the R6 to R8 The remainders where at least one adjacent pair of R8 is not combined to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms are the same or different, and are each independently hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 R6 내지 R8 중 적어도 하나의 인접한 어느 한 쌍 이상이 서로 결합하여 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성하고, 상기 R6 내지 R8 중 적어도 하나의 인접한 어느 한 쌍 이상이 서로 결합하여 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성하지 않는 나머지는 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, at least one adjacent pair of R6 to R8 is bonded to each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, and at least one of R6 to R8 The remainders in which one or more adjacent pairs do not combine to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms are the same or different, and are each independently hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 R6 내지 R8 중 적어도 하나의 인접한 어느 한 쌍 이상이 서로 결합하여 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성하고, 상기 R6 내지 R8 중 적어도 하나의 인접한 어느 한 쌍 이상이 서로 결합하여 탄소수 6 내지 20의 단환 또는 다환의 방향족 탄화수소고리를 형성하지 않는 나머지는 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, at least one adjacent pair of R6 to R8 is bonded to each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms, and at least one of R6 to R8 The remainders in which one or more adjacent pairs do not combine to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms are the same or different, and are each independently hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 R6 내지 R8 중 적어도 하나의 인접한 어느 한 쌍 이상이 서로 결합하여 벤젠을 형성하고, 상기 R6 내지 R8 중 적어도 하나의 인접한 어느 한 쌍 이상이 서로 결합하여 벤젠을 형성하지 않는 나머지는 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, one or more adjacent pairs of at least one of R6 to R8 combine with each other to form benzene, and one or more adjacent pairs of at least one of R6 to R8 combine to form benzene. The remainders that do not form are the same or different from each other, and are each independently hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r6은 2 내지 4이고, 상기 R6 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r6 is 2 to 4, and one or more adjacent pairs of R6 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r6은 2 내지 4이고, 상기 R6 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r6 is 2 to 4, and any one or more adjacent pairs of R6 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r6은 2 내지 4이고, 상기 R6 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 6 내지 30의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to one embodiment of the present specification, r6 is 2 to 4, any one or more adjacent pairs of R6 are combined with each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r6은 2 내지 4이고, 상기 R6 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 6 내지 20의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r6 is 2 to 4, any one or more adjacent pairs of R6 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r6은 2 내지 4이고, 상기 R6 중 인접한 어느 한 쌍 이상은 서로 결합하여 벤젠을 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r6 is 2 to 4, any one or more adjacent pairs of R6 are combined with each other to form benzene, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r7은 2 내지 4이고, 상기 R7 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r7 is 2 to 4, and one or more adjacent pairs of R7 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r7은 2 내지 4이고, 상기 R7 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r7 is 2 to 4, and one or more adjacent pairs of R7 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r7은 2 내지 4이고, 상기 R7 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 6 내지 30의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r7 is 2 to 4, and one or more adjacent pairs of R7 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r7은 2 내지 4이고, 상기 R7 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 6 내지 20의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r7 is 2 to 4, any one or more adjacent pairs of R7 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r7은 2 내지 4이고, 상기 R7 중 인접한 어느 한 쌍 이상은 서로 결합하여 벤젠을 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r7 is 2 to 4, any one or more adjacent pairs of R7 are combined with each other to form benzene, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r8은 2 내지 5이고, 상기 R8 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r8 is 2 to 5, and any one or more adjacent pairs of R8 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r8은 2 내지 5이고, 상기 R8 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r8 is 2 to 5, and any one or more adjacent pairs of R8 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r8은 2 내지 5이고, 상기 R8 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 6 내지 30의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r8 is 2 to 5, any one or more adjacent pairs of R8 are combined with each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r8은 2 내지 5이고, 상기 R8 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 6 내지 20의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r8 is 2 to 5, any one or more adjacent pairs of R8 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r8은 2 내지 5이고, 상기 R8 중 인접한 어느 한 쌍 이상은 서로 결합하여 벤젠을 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r8 is 2 to 5, any one or more adjacent pairs of R8 are combined with each other to form benzene, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r'6은 2 내지 4이고, 상기 R'6 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to one embodiment of the present specification, r'6 is 2 to 4, and any one or more adjacent pairs of R'6 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r'6은 2 내지 4이고, 상기 R'6 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to one embodiment of the present specification, r'6 is 2 to 4, and any one or more adjacent pairs of R'6 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms, the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r'6은 2 내지 4이고, 상기 R'6 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 6 내지 30의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r'6 is 2 to 4, any one or more adjacent pairs of R'6 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r'6은 2 내지 4이고, 상기 R'6 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 6 내지 20의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to one embodiment of the present specification, r'6 is 2 to 4, and any one or more adjacent pairs of R'6 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r'6은 2 내지 4이고, 상기 R'6 중 인접한 어느 한 쌍 이상은 서로 결합하여 벤젠을 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r'6 is 2 to 4, any one or more adjacent pairs of R'6 are combined with each other to form benzene, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r'7은 2 내지 4이고, 상기 R'7 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to one embodiment of the present specification, r'7 is 2 to 4, and any one or more adjacent pairs of R'7 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r'7은 2 내지 4이고, 상기 R'7 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to one embodiment of the present specification, r'7 is 2 to 4, and any one or more adjacent pairs of R'7 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms, the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r'7은 2 내지 4이고, 상기 R'7 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 6 내지 30의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to one embodiment of the present specification, r'7 is 2 to 4, any one or more adjacent pairs of R'7 are combined with each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r'7은 2 내지 4이고, 상기 R'7 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 6 내지 20의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r'7 is 2 to 4, any one or more adjacent pairs of R'7 are combined with each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r'7은 2 내지 4이고, 상기 R'7 중 인접한 어느 한 쌍 이상은 서로 결합하여 벤젠을 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r'7 is 2 to 4, any one or more adjacent pairs of R'7 are combined with each other to form benzene, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r'8은 2 내지 5이고, 상기 R'8 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 30의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to one embodiment of the present specification, r'8 is 2 to 5, and any one or more adjacent pairs of R'8 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r'8은 2 내지 5이고, 상기 R'8 중 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 탄소수 6 내지 20의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r'8 is 2 to 5, and any one or more adjacent pairs of R'8 are bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 20 carbon atoms, the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r'8은 2 내지 5이고, 상기 R'8 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 6 내지 30의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r'8 is 2 to 5, any one or more adjacent pairs of R'8 are combined with each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms, and the remainder is hydrogen; Or it is deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r'8은 2 내지 5이고, 상기 R'8 중 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 6 내지 20의 방향족 탄화수소고리를 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r'8 is 2 to 5, any one or more adjacent pairs of R'8 are bonded to each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 r'8은 2 내지 5이고, 상기 R'8 중 인접한 어느 한 쌍 이상은 서로 결합하여 벤젠을 형성하고, 나머지는 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, r'8 is 2 to 5, any one or more adjacent pairs of R'8 are combined with each other to form benzene, and the remainder is hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화합물 중에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, Formula 1 is any one selected from the following compounds.
Figure PCTKR2023004877-appb-img-000021
Figure PCTKR2023004877-appb-img-000021
Figure PCTKR2023004877-appb-img-000022
Figure PCTKR2023004877-appb-img-000022
Figure PCTKR2023004877-appb-img-000023
Figure PCTKR2023004877-appb-img-000023
Figure PCTKR2023004877-appb-img-000024
Figure PCTKR2023004877-appb-img-000024
Figure PCTKR2023004877-appb-img-000025
Figure PCTKR2023004877-appb-img-000025
Figure PCTKR2023004877-appb-img-000026
Figure PCTKR2023004877-appb-img-000026
Figure PCTKR2023004877-appb-img-000027
Figure PCTKR2023004877-appb-img-000027
Figure PCTKR2023004877-appb-img-000028
Figure PCTKR2023004877-appb-img-000028
Figure PCTKR2023004877-appb-img-000029
Figure PCTKR2023004877-appb-img-000029
Figure PCTKR2023004877-appb-img-000030
Figure PCTKR2023004877-appb-img-000030
Figure PCTKR2023004877-appb-img-000031
Figure PCTKR2023004877-appb-img-000031
Figure PCTKR2023004877-appb-img-000032
Figure PCTKR2023004877-appb-img-000032
Figure PCTKR2023004877-appb-img-000033
Figure PCTKR2023004877-appb-img-000033
Figure PCTKR2023004877-appb-img-000034
Figure PCTKR2023004877-appb-img-000034
Figure PCTKR2023004877-appb-img-000035
Figure PCTKR2023004877-appb-img-000035
Figure PCTKR2023004877-appb-img-000036
Figure PCTKR2023004877-appb-img-000036
Figure PCTKR2023004877-appb-img-000037
Figure PCTKR2023004877-appb-img-000037
Figure PCTKR2023004877-appb-img-000038
Figure PCTKR2023004877-appb-img-000038
Figure PCTKR2023004877-appb-img-000039
Figure PCTKR2023004877-appb-img-000039
Figure PCTKR2023004877-appb-img-000040
Figure PCTKR2023004877-appb-img-000040
또한, 본 명세서는 상기 전술한 화합물을 포함하는 유기 발광 소자를 제공한다.Additionally, the present specification provides an organic light-emitting device containing the above-mentioned compound.
본 명세서에서 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In this specification, when a member is said to be located “on” another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.
본 명세서에서 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다. In this specification, when a part “includes” a certain component, this means that it may further include other components rather than excluding other components, unless specifically stated to the contrary.
본 명세서에 있어서, 상기 '층'은 본 기술분야에 주로 사용되는 '필름'과 호환되는 의미이며, 목적하는 영역을 덮는 코팅을 의미한다. 상기 '층'의 크기는 한정되지 않으며, 각각의 '층'은 그 크기가 같거나 상이할 수 있다. 일 실시상태에 따르면, '층'의 크기는 전체 소자와 같을 수 있고, 특정 기능성 영역의 크기에 해당할 수 있으며, 단일 서브픽셀(sub-pixel)만큼 작을 수도 있다. In this specification, the 'layer' is interchangeable with the 'film' mainly used in the present technical field, and refers to a coating that covers the target area. The size of the 'layer' is not limited, and each 'layer' may be the same or different in size. According to one embodiment, the size of a 'layer' may be the same as the entire device, may correspond to the size of a specific functional area, or may be as small as a single sub-pixel.
본 명세서에 있어서, 특정한 A 물질이 B층에 포함된다는 의미는 i) 1종 이상의 A 물질이 하나의 B층에 포함되는 것과 ii) B층이 1층 이상으로 구성되고, A 물질이 다층의 B층 중 1층 이상에 포함되는 것을 모두 포함한다.In this specification, the inclusion of a specific material A in the layer B means that i) one or more types of material A are included in one layer B, and ii) the layer B consists of one or more layers, and the material A is included in a multi-layer B. Includes everything on the first or higher floors.
본 명세서에 있어서, 특정한 A 물질이 C층 또는 D층에 포함된다는 의미는 i) 1층 이상의 C층 중 1층 이상에 포함되거나, ii) 1층 이상의 D층 중 1층 이상에 포함되거나, iii) 1층 이상의 C층 및 1층 이상의 D층에 각각 포함되는 것을 모두 의미하는 것이다.In this specification, the meaning that a specific material A is included in the C layer or D layer means that it is i) included in one or more layers of one or more layers of C, ii) included in one or more layers of one or more layers of D, or iii ) This means that it is included in each of the C floors above the first floor and the D floors above the first floor.
본 명세서는 제1 전극; 제2 전극; 및 상기 제1 전극과 상기 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1 층 이상은 상기 화학식 1의 화합물을 포함하는 것인 유기 발광 소자를 제공한다.This specification includes: a first electrode; second electrode; and an organic light emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound of Formula 1.
본 명세서의 유기 발광 소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 정공 주입층, 정공 수송층, 발광층, 전자 수송층, 전자 주입층, 전자 차단층, 정공 차단층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc. However, the structure of the organic light emitting device is not limited to this and may include fewer organic layers.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 정공주입층, 정공 수송층, 또는 정공 주입 및 수송층을 포함하고, 상기 정공주입층, 정공수송층, 또는 정공 주입 및 수송층은 상기 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the compound.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 전자 차단층을 포함하고, 상기 전자 차단층은 상기 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 전자주입층, 전자 수송층, 또는 전자 주입 및 수송층을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, or an electron injection and transport layer.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 발광층을 포함한다.According to an exemplary embodiment of the present specification, the organic material layer includes a light-emitting layer.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 정공 차단층을 포함한다. According to an exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 정공 주입층, 정공 수송층, 정공 주입 및 수송층, 발광층, 전자 수송층, 전자 주입층, 전자 주입 및 수송층, 정공 차단층 및 전자 차단층으로 이루어진 군에서 선택되는 1층 또는 2층 이상을 더 포함한다.According to an exemplary embodiment of the present specification, the organic light emitting device is a group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer. It further includes one or more floors selected from.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 제1 전극; 상기 제1 전극과 대향하여 구비된 제2 전극; 상기 제1 전극과 상기 제2 전극 사이에 구비된 발광층; 및 상기 발광층과 상기 제1 전극 사이, 또는 상기 발광층과 상기 제2 전극 사이에 구비된 2층 이상의 유기물층을 포함한다. According to an exemplary embodiment of the present specification, the organic light emitting device includes a first electrode; a second electrode provided opposite to the first electrode; a light emitting layer provided between the first electrode and the second electrode; and two or more organic material layers provided between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.
본 명세서의 일 실시상태에 따르면, 상기 2층 이상의 유기물층은 정공 주입층, 정공 수송층, 정공 주입 및 수송층, 발광층, 전자 수송층, 전자 주입층, 전자 주입 및 수송층, 정공 차단층 및 전자 차단층으로 이루어진 군에서 2 이상이 선택될 수 있다.According to an exemplary embodiment of the present specification, the two or more organic material layers are composed of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer. Two or more may be selected from the group.
본 명세서의 일 실시상태에 따르면, 상기 발광층과 상기 제1 전극 사이에 2층 이상의 정공수송층을 포함한다. 상기 2층 이상의 정공수송층은 서로 동일하거나 상이한 물질을 포함할 수 있다.According to an exemplary embodiment of the present specification, a hole transport layer of two or more layers is included between the light emitting layer and the first electrode. The two or more hole transport layers may include the same or different materials.
본 명세서의 일 실시상태에 따르면, 상기 제1 전극은 애노드 또는 캐소드이다.According to an exemplary embodiment of the present specification, the first electrode is an anode or a cathode.
본 명세서의 일 실시상태에 따르면, 상기 제2 전극은 캐소드 또는 애노드이다.According to an exemplary embodiment of the present specification, the second electrode is a cathode or anode.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 기판 상에 애노드, 1층 이상의 유기물층 및 캐소드이 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. According to an exemplary embodiment of the present specification, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 기판 상에 캐소드, 1층 이상의 유기물층 및 애노드가 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다.According to an exemplary embodiment of the present specification, the organic light emitting device may be an inverted type organic light emitting device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
예컨대, 본 명세서의 일 실시상태에 따른 유기 발광 소자의 구조가 도 1 및 2에 예시되어 있다. 상기 도 1 및 2는 유기 발광 소자를 예시한 것이며 이에 한정되는 것은 아니다. For example, the structure of an organic light-emitting device according to an exemplary embodiment of the present specification is illustrated in FIGS. 1 and 2. 1 and 2 illustrate an organic light emitting device and are not limited thereto.
도 1에는 기판(1) 위에 제1 전극(2), 유기물층(4) 및 제2 전극(3)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 상기 화합물은 유기물층에 포함된다.Figure 1 illustrates the structure of an organic light-emitting device in which a first electrode 2, an organic material layer 4, and a second electrode 3 are sequentially stacked on a substrate 1. The compound is included in the organic layer.
도 2에는 기판(1) 위에 제1 전극(2), 정공주입층(5), 정공수송층(6), 전자차단층(7), 발광층(8), 정공차단층(9), 전자주입 및 수송층(10) 및 제2 전극(3)이 순차적으로 적층된 유기 발광 소자의 구조가 예시되어 있다. 상기 화합물은 정공주입층(5), 정공수송층(6), 또는 전자차단층(7)에 포함된다.2 shows a first electrode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 8, a hole blocking layer 9, an electron injection layer, and The structure of an organic light emitting device in which the transport layer 10 and the second electrode 3 are sequentially stacked is illustrated. The compound is included in the hole injection layer (5), the hole transport layer (6), or the electron blocking layer (7).
본 명세서의 유기 발광 소자는 정공주입층, 정공 수송층, 정공 주입 및 수송층, 또는 전자차단층이 상기 화합물, 즉 상기 화학식 1의 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. The organic light emitting device of the present specification is made of materials and methods known in the art, except that the hole injection layer, hole transport layer, hole injection and transport layer, or electron blocking layer includes the above compound, that is, the compound of Formula 1 above. can be manufactured.
상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다.When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
예컨대, 본 명세서의 유기 발광 소자는 기판 상에 제1 전극, 유기물층 및 제2 전극을 순차적으로 적층시킴으로써 제조할 수 있다. 이 때, 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 PVD(physical Vapor Deposition)방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 애노드를 형성하고, 그 위에 정공 주입층, 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물층을 형성한 후, 그 위에 음극으로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 캐소드 물질, 유기물층 및 애노드 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다. For example, the organic light emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode. It can be manufactured by forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
또한, 상기 화학식 1의 화합물은 유기 발광 소자의 제조 시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하나, 이에 한정되는 것은 아니다. In addition, the compound of Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.
이와 같은 방법 외에도, 기판 상에 캐소드 물질로부터 유기물층, 애노드 물질을 차례로 증착시켜 유기 발광 소자를 만들 수도 있다. 다만, 제조 방법이 이에 한정되는 것은 아니다. In addition to this method, an organic light-emitting device can also be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. However, the manufacturing method is not limited to this.
본 명세서에서 상기 기판은 제1 전극 또는 제 2 전극일 수 있다.In this specification, the substrate may be a first electrode or a second electrode.
상기 애노드 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 예를 들어, 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO), 인듐아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2 : Sb와 같은 금속과 산화물의 조합; 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이에 한정되는 것은 아니다. The anode material is generally preferably a material with a large work function to facilitate hole injection into the organic layer. For example, metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO:Al or SnO 2 : A combination of a metal such as Sb and an oxide; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline are included, but are not limited thereto.
상기 캐소드 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 예를 들어, 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이에 한정되는 것은 아니다.The cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer. metals or alloys thereof, for example magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead; Examples include, but are not limited to, multi-layered materials such as LiF/Al or LiO 2 /Al.
상기 발광층은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로, 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되는 것은 아니다.The light emitting layer may include a host material and a dopant material. Host materials include condensed aromatic ring derivatives or heterocyclic ring-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include dibenzofuran derivatives, ladder-type furan compounds, These include, but are not limited to, pyrimidine derivatives.
본 명세서의 일 실시상태에 따르면, 상기 호스트는 하기 화학식 H-1로 표시되는 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the host includes, but is not limited to, a compound represented by the following formula H-1.
[화학식 H-1][Formula H-1]
Figure PCTKR2023004877-appb-img-000041
Figure PCTKR2023004877-appb-img-000041
상기 화학식 H-1에 있어서,In the above formula H-1,
L20 및 L21은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 2가의 헤테로고리기이고,L20 and L21 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,Ar20 and Ar21 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
R201은 수소; 중수소; 할로겐기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,R201 is hydrogen; heavy hydrogen; halogen group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
r201은 1 내지 8의 정수이며, 상기 r201이 2 이상인 경우, 2 이상의 R201은 서로 같거나 상이하다.r201 is an integer from 1 to 8, and when r201 is 2 or more, 2 or more R201 are the same or different from each other.
본 명세서의 일 실시상태에 있어서, 상기 L20 및 L21은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기; 또는 탄소수 2 내지 30의 단환 또는 다환의 2가의 헤테로고리기이다.In an exemplary embodiment of the present specification, L20 and L21 are the same or different from each other and are each independently directly bonded; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or it is a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 L20 및 L21은 서로 동일하거나 상이하고, 각각 독립적으로 직접결합; 중수소로 치환 또는 비치환된 페닐렌기; 중수소로 치환 또는 비치환된 바이페닐릴렌기; 중수소로 치환 또는 비치환된 나프틸렌기; 2가의 디벤조퓨란기; 또는 2가의 디벤조티오펜기이다.In an exemplary embodiment of the present specification, L20 and L21 are the same or different from each other and are each independently directly bonded; A phenylene group substituted or unsubstituted with deuterium; A biphenylylene group substituted or unsubstituted with deuterium; Naphthylene group substituted or unsubstituted with deuterium; divalent dibenzofuran group; Or it is a divalent dibenzothiophene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로고리기다.In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 20의 단환 내지 4환의 아릴기; 또는 치환 또는 비치환된 탄소수 6 내지 20의 단환 내지 4환의 헤테로고리기다.In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic to 4-ring heterocyclic group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 중수소, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 페닐기; 중수소, 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 바이페닐기; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 나프틸기; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 디벤조퓨란기; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 나프토벤조퓨란기; 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 디벤조티오펜기; 또는 탄소수 6 내지 20의 단환 또는 다환의 아릴기로 치환 또는 비치환된 나프토벤조티오펜기이다.In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; A biphenyl group substituted or unsubstituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Dibenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Naphthobenzofuran group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Dibenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or it is a naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
본 명세서의 일 실시상태에 있어서, 상기 Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 중수소로 치환 또는 비치환된 페닐기; 중수소로 치환 또는 비치환된 바이페닐기; 터페닐기; 중수소로 치환 또는 비치환된 나프틸기; 페난트렌기; 디벤조퓨란기; 나프토벤조퓨란기; 디벤조티오펜기; 또는 나프토벤조티오펜기이다.In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium; Biphenyl group substituted or unsubstituted with deuterium; Terphenyl group; Naphthyl group substituted or unsubstituted with deuterium; phenanthrene group; Dibenzofuran group; Naphthobenzofuran group; Dibenzothiophene group; Or it is a naphthobenzothiophene group.
본 명세서의 일 실시상태에 있어서, 상기 Ar20은 치환 또는 비치환된 헤테로고리기이고, 상기 Ar21은 치환 또는 비치환된 아릴기이다.In one embodiment of the present specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 있어서, 상기 Ar20 및 Ar21은 서로 동일하거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이다.In an exemplary embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 따르면, 상기 R201은 수소; 또는 페닐기이다.According to an exemplary embodiment of the present specification, R201 is hydrogen; Or it is a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 H-1은 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, the formula H-1 is represented by the following compound.
Figure PCTKR2023004877-appb-img-000042
Figure PCTKR2023004877-appb-img-000042
상기 도펀트 재료로는 방향족 아민 유도체, 스트릴아민 화합물, 붕소 착체, 플루오란텐 화합물, 금속 착체 등이 있다. 구체적으로, 방향족 아민 유도체로는 치환 또는 비치환된 아릴아민기를 갖는 축합 방향족환 유도체로서, 아릴아민기를 갖는 피렌, 안트라센, 크리센, 페리플란텐 등이 있다. 또한, 스티릴아민 화합물은 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기, 실릴기, 알킬기, 시클로알킬기 및 아릴아민기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민, 스티릴디아민, 스티릴트리아민, 스티릴테트라아민 등이 있으나, 이에 한정되지 않는다. 또한, 금속 착체로는 이리듐 착체, 백금 착체 등이 있으나, 이에 한정되는 것은 아니다.The dopant materials include aromatic amine derivatives, strylamine compounds, boron complexes, fluoranthene compounds, and metal complexes. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamine group, and include pyrene, anthracene, chrysene, periplanthene, etc. having an arylamine group. In addition, a styrylamine compound is a compound in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, and is one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group, and an arylamine group. The substituent is substituted or unsubstituted. Specifically, styrylamine, styryldiamine, styryltriamine, styryltetraamine, etc. are included, but are not limited thereto. Additionally, metal complexes include, but are not limited to, iridium complexes and platinum complexes.
본 명세서의 일 실시상태에 따르면, 상기 도펀트 재료는 하기 화학식 D-1의 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the dopant material includes, but is not limited to, a compound of the following formula D-1.
[화학식 D-1][Formula D-1]
Figure PCTKR2023004877-appb-img-000043
Figure PCTKR2023004877-appb-img-000043
상기 화학식 D-1에 있어서,In Formula D-1,
L101 및 L102는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 아릴렌기이고,L101 and L102 are the same or different from each other and are each independently directly bonded; Or a substituted or unsubstituted arylene group,
Ar101 내지 Ar104는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.Ar101 to Ar104 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 따르면, 상기 L101 및 L102는 직접결합이다.According to an exemplary embodiment of the present specification, L101 and L102 are a direct bond.
본 명세서의 일 실시상태에 따르면, 상기 Ar101 내지 Ar104는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar101 내지 Ar104는 서로 같거나 상이하고, 각각 독립적으로 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기; 또는 탄소수 2 내지 30의 단환 또는 다환의 헤테로아릴기이다.According to an exemplary embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl having 6 to 30 carbon atoms that is substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. energy; Or it is a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar101 내지 Ar104는 서로 같거나 상이하고, 각각 독립적으로 페닐기; 메틸기로 치환된 페닐기; 또는 디벤조퓨란기이다.According to an exemplary embodiment of the present specification, Ar101 to Ar104 are the same as or different from each other, and are each independently a phenyl group; A phenyl group substituted with a methyl group; Or it is a dibenzofuran group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 D-1는 하기 화합물일 수 있으나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, Formula D-1 may be the following compound, but is not limited thereto.
Figure PCTKR2023004877-appb-img-000044
Figure PCTKR2023004877-appb-img-000044
상기 정공 주입층은 전극으로부터 정공을 수취하는 층이다. 정공 주입 물질은 정공을 수송하는 능력을 가져 애노드로부터 정공 수취 효과 및 발광층 또는 발광 재료에 대하여 우수한 정공 주입 효과를 갖는 것이 바람직하다. 또한, 발광층에서 생성된 엑시톤의 전자 주입층 또는 전자 주입 재료에의 이동을 방지할 수 있는 능력이 우수한 물질이 바람직하다. 또한, 박막 형성 능력이 우수한 물질이 바람직하다. 또한, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 애노드 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는, 금속 포피린(porphyrin), 올리고티오펜, 아릴아민 계열의 유기물; 헥사니트릴헥사아자트리페닐렌 계열의 유기물; 퀴나크리돈(quinacridone)계열의 유기물; 페릴렌(perylene) 계열의 유기물; 안트라퀴논, 폴리아닐린과 같은 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이에 한정 되는 것은 아니다.The hole injection layer is a layer that receives holes from the electrode. The hole injection material preferably has the ability to transport holes and has an excellent hole receiving effect from the anode and an excellent hole injection effect to the light emitting layer or light emitting material. Additionally, a material that has an excellent ability to prevent the movement of excitons generated in the light-emitting layer to the electron injection layer or electron injection material is desirable. Additionally, materials with excellent thin film forming ability are desirable. Additionally, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrin, oligothiophene, and arylamine-based organic materials; Hexanitrilehexaazatriphenylene series organic substances; Organic substances of the quinacridone series; Perylene-based organic substances; These include, but are not limited to, polythiophene-based conductive polymers such as anthraquinone and polyaniline.
본 명세서의 일 실시상태에 따르면, 상기 정공주입층은 하기 화학식 HI-1의 화합물을 포함하나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound of the following formula HI-1.
[화학식 HI-1][Formula HI-1]
Figure PCTKR2023004877-appb-img-000045
Figure PCTKR2023004877-appb-img-000045
상기 화학식 HI-1에 있어서,In the formula HI-1,
X'1 내지 X'6 중 적어도 하나는 N이고, 나머지는 CH이며,At least one of X'1 to X'6 is N, and the remainder is CH,
R309 내지 R314은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.R309 to R314 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heteroaryl group, or it combines with adjacent groups to form a substituted or unsubstituted ring.
본 명세서의 일 실시상태에 따르면, 상기 X'1 내지 X'6는 N이다.According to an exemplary embodiment of the present specification, X'1 to X'6 are N.
본 명세서의 일 실시상태에 따르면, 상기 R309 내지 R314는 시아노기이다.According to an exemplary embodiment of the present specification, R309 to R314 are cyano groups.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HI-1은 하기 화합물일 수 있으나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the formula HI-1 may be the following compound, but is not limited thereto.
Figure PCTKR2023004877-appb-img-000046
Figure PCTKR2023004877-appb-img-000046
상기 정공 수송층은 정공 주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층이다. 본 명세서의 일 실시상태에 따른 유기 발광 소자가 상기 화학식 1을 포함하는 정공수송층 이외의 추가의 정공수송층을 포함하는 경우, 정공 수송 물질로는 애노드나 정공 주입층으로부터 정공을 수취하여 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 바람직하다. 구체적인 예로는, 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이에 한정되는 것은 아니다.The hole transport layer is a layer that receives holes from the hole injection layer and transports the holes to the light emitting layer. When the organic light emitting device according to an exemplary embodiment of the present specification includes an additional hole transport layer other than the hole transport layer containing Formula 1, the hole transport material is a hole transport material that receives holes from the anode or hole injection layer and transfers them to the light emitting layer. A material with high mobility for holes is preferred. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions.
본 명세서의 일 실시상태에 따르면, 상기 정공수송층은 하기 화학식 HT-1로 표시되는 화합물을 포함하나, 이에 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the hole transport layer includes a compound represented by the following formula HT-1, but is not limited thereto.
[화학식 HT-1][Formula HT-1]
Figure PCTKR2023004877-appb-img-000047
Figure PCTKR2023004877-appb-img-000047
상기 화학식 HT-1에 있어서,In the formula HT-1,
L501 및 L502는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L501 and L502 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R501 및 Ar501 내지 Ar504는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.R501 and Ar501 to Ar504 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 따르면, 상기 L501 및 L502는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, L501 and L502 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L501 및 L502는 페닐렌기이다.According to an exemplary embodiment of the present specification, L501 and L502 are phenylene groups.
본 명세서의 일 실시상태에 따르면, 상기 R501 및 Ar501 내지 Ar504는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R501 and Ar501 to Ar504 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R501 및 Ar501 내지 Ar504는 페닐기; 또는 나프틸기이다.According to an exemplary embodiment of the present specification, R501 and Ar501 to Ar504 are phenyl groups; Or it is a naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HT-1은 하기 화합물로 표시된다.According to an exemplary embodiment of the present specification, the formula HT-1 is represented by the following compound.
Figure PCTKR2023004877-appb-img-000048
Figure PCTKR2023004877-appb-img-000048
상기 전자 수송층은 전자 주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층이다. 전자 수송 물질로는 캐소드로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 바람직하다. 구체적인 예로는, 8-히드록시퀴놀린의 Al착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이에 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이, 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히, 적절한 캐소드 물질은 낮은 일함수를 가지며, 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로, 세슘, 바륨, 칼슘, 이테르븀 및 사마륨 등이 있고, 각 경우 알루미늄층 또는 실버층이 뒤따른다.The electron transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer. The electron transport material is a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high mobility for electrons is preferred. Specific examples include Al complex of 8-hydroxyquinoline; Complex containing Alq 3 ; organic radical compounds; These include, but are not limited to, hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material, as used according to the prior art. In particular, suitable cathode materials are conventional materials with a low work function followed by an aluminum or silver layer. Specifically, there are cesium, barium, calcium, ytterbium, and samarium, and in each case, an aluminum layer or a silver layer follows.
상기 전자 주입층은 전극으로부터 전자를 수취하는 층이다. 전자 주입물로는 전자를 수송하는 능력이 우수하고, 제2 전극으로부터의 전자 수취 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 갖는 것이 바람직하다. 또한, 발광층에서 생성된 엑시톤이 정공 주입층으로 이동하는 것을 방지하고, 박막 형성 능력이 우수한 물질이 바람직하다. 구체적으로는, 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 함질소 5원환 유도체 등이 있으나, 이에 한정되는 것은 아니다. The electron injection layer is a layer that receives electrons from the electrode. It is preferable that the electron injection material has an excellent ability to transport electrons, has an excellent electron receiving effect from the second electrode, and has an excellent electron injection effect with respect to the light emitting layer or light emitting material. In addition, a material that prevents excitons generated in the light-emitting layer from moving to the hole injection layer and has excellent thin film forming ability is desirable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, These include, but are not limited to, metal complex compounds and nitrogen-containing five-membered ring derivatives.
상기 금속 착체 화합물로는 8-히드록시퀴놀리나토 리튬, 비스(8-히드록시퀴놀리나토)아연, 비스(8-히드록시퀴놀리나토)구리, 비스(8-히드록시퀴놀리나토)망간, 트리스(8-히드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-히드록시퀴놀리나토)알루미늄, 트리스(8-히드록시퀴놀리나토)갈륨, 비스(10-히드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-히드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되는 것은 아니다.The metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, and bis(8-hydroxyquinolinato)manganese. , tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h) ]Quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato) There are (o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato) aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato) gallium. , but is not limited to this.
본 명세서의 일 실시상태에 따르면, 상기 전자 주입 및 수송층은 전자를 발광층까지 수송하는 층이다. 상기 전자 주입 및 수송층은 상기 전자 수송층 및 전자주입층에서 예시한 물질을 사용할 수 있으나, 이에 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the electron injection and transport layer is a layer that transports electrons to the light-emitting layer. The electron injection and transport layer may use materials exemplified for the electron transport layer and electron injection layer, but is not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 전자 주입 및 수송층은 하기 화학식 ET-1로 표시되는 화합물을 포함하나, 이에 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the electron injection and transport layer includes a compound represented by the following formula ET-1, but is not limited thereto.
[화학식 ET-1][Formula ET-1]
Figure PCTKR2023004877-appb-img-000049
Figure PCTKR2023004877-appb-img-000049
상기 화학식 ET-1에 있어서,In the formula ET-1,
Z11 내지 Z13 중 적어도 하나는 N이고, 나머지는 CH이고,At least one of Z11 to Z13 is N, the others are CH,
Z21 내지 Z23 중 적어도 하나는 N이고, 나머지는 CH이며,At least one of Z21 to Z23 is N, the others are CH,
L601 및 L602는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L601 and L602 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
Ar601 내지 Ar604는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다.Ar601 to Ar604 are the same or different from each other, and are each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
본 명세서의 일 실시상태에 따르면, 상기 L601 및 L602는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, L601 and L602 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L601 및 L602는 페닐렌기이다.According to an exemplary embodiment of the present specification, L601 and L602 are phenylene groups.
본 명세서의 일 실시상태에 따르면, 상기 Ar601 내지 Ar604는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar601 to Ar604 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar601 내지 Ar604는 페닐기이다.According to an exemplary embodiment of the present specification, Ar601 to Ar604 are phenyl groups.
본 명세서의 일 실시상태에 따르면, 상기 화학식 ET-1은 하기 화합물일 수 있으나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the chemical formula ET-1 may be the following compound, but is not limited thereto.
Figure PCTKR2023004877-appb-img-000050
Figure PCTKR2023004877-appb-img-000050
상기 전자 차단층은 전자 주입층으로부터 주입된 전자가 발광층을 지나 정공 주입층으로 진입하는 것을 방지하여 소자의 수명과 효율을 향상시킬 수 있는 층이다. 본 명세서의 일 실시상태에 따른 유기 발광 소자가 상기 화학식 1을 포함하는 전자 차단층 이외의 추가의 전자차단층을 포함하는 경우, 공지된 재료는 제한 없이 사용 가능하며, 상기 정공주입층 또는 정공수송층의 설명에서 예시한 물질을 사용할 수 있으나, 이에만 한정되는 것은 아니다. 상기 전자차단층은 발광층과 정공수송층 사이에, 발광층과 정공 주입층 사이에, 또는 발광층과 정공 주입 및 정공 수송을 동시에 하는 층 사이에 형성될 수 있다. The electron blocking layer is a layer that can improve the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer. When the organic light emitting device according to an embodiment of the present specification includes an additional electron blocking layer other than the electron blocking layer containing Formula 1, known materials can be used without limitation, and the hole injection layer or the hole transport layer The materials exemplified in the description may be used, but are not limited thereto. The electron blocking layer may be formed between a light-emitting layer and a hole transport layer, between a light-emitting layer and a hole injection layer, or between a light-emitting layer and a layer that simultaneously performs hole injection and hole transport.
상기 정공 차단층은 정공이 캐소드로 도달을 저지하는 층으로, 일반적으로 전자 주입층과 동일한 조건으로 형성될 수 있다. 구체적으로, 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, 알루미늄 착물 (aluminum complex) 등이 있으나, 이에 한정되는 것은 아니다.The hole blocking layer is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc. are included, but are not limited thereto.
상기 정공 차단층은 정공이 캐소드로 도달을 저지하는 층으로, 일반적으로 전자 주입층과 동일한 조건으로 형성될 수 있다. 구체적으로, 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, 알루미늄 착물 (aluminum complex) 등이 있으나, 이에 한정되는 것은 아니다.The hole blocking layer is a layer that prevents holes from reaching the cathode, and can generally be formed under the same conditions as the electron injection layer. Specifically, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc. are included, but are not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 정공차단층은 하기 화학식 HB-1로 표시되는 화합물을 포함하나, 이에 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the hole blocking layer includes a compound represented by the following formula HB-1, but is not limited thereto.
[화학식 HB-1][Formula HB-1]
Figure PCTKR2023004877-appb-img-000051
Figure PCTKR2023004877-appb-img-000051
상기 화학식 HB-1에 있어서,In the formula HB-1,
Z31 내지 Z33 중 적어도 하나는 N이고, 나머지는 CH이며,At least one of Z31 to Z33 is N, and the remainder is CH,
L603는 직접결합; 치환 또는 비치환된 아릴렌기; 또는 치환 또는 비치환된 헤테로아릴렌기이고,L603 is directly bonded; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
R601 내지 R603은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,R601 to R603 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
Ar605 및 Ar606는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 기와 서로 결합하여 고리를 형성하고,Ar605 and Ar606 are the same or different from each other, and are each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heteroaryl group, or forms a ring by combining with adjacent groups,
l603은 1 내지 3의 정수이고, 상기 l603이 2 이상인 경우, 상기 2 이상의 L603은 서로 같거나 상이하며,l603 is an integer from 1 to 3, and when l603 is 2 or more, the 2 or more L603 are the same or different from each other,
r601은 1 내지 4의 정수이고, 상기 r601이 2 이상인 경우, 상기 2 이상의 R601은 서로 같거나 상이하고,r601 is an integer from 1 to 4, and when r601 is 2 or more, the 2 or more R601 are the same or different from each other,
r602은 1 내지 4의 정수이고, 상기 r602이 2 이상인 경우, 상기 2 이상의 R602은 서로 같거나 상이하며,r602 is an integer from 1 to 4, and when r602 is 2 or more, the 2 or more R602 are the same or different from each other,
r603은 1 내지 3의 정수이고, 상기 r603이 2 이상인 경우, 상기 2 이상의 R603은 서로 같거나 상이하다.r603 is an integer of 1 to 3, and when r603 is 2 or more, the 2 or more R603s are the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 Z31 내지 Z33는 N이다.According to an exemplary embodiment of the present specification, Z31 to Z33 are N.
본 명세서의 일 실시상태에 따르면, 상기 L603는 직접결합; 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, L603 is a direct bond; Or it is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 L603는 직접결합; 페닐렌기; 나프틸렌기; 또는 바이페닐릴렌기이다.According to an exemplary embodiment of the present specification, L603 is a direct bond; phenylene group; naphthylene group; Or it is a biphenylylene group.
본 명세서의 일 실시상태에 따르면, 상기 L603는 페닐렌기; 또는 나프틸렌기이다.According to an exemplary embodiment of the present specification, L603 is a phenylene group; Or it is a naphthylene group.
본 명세서의 일 실시상태에 따르면, 상기 l603은 2이다.According to an exemplary embodiment of the present specification, l603 is 2.
본 명세서의 일 실시상태에 따르면, 상기 R601 내지 R603은 수소이다.According to an exemplary embodiment of the present specification, R601 to R603 are hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 Ar605 및 Ar606는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar605 and Ar606 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 Ar605 및 Ar606는 서로 같거나 상이하고, 각각 독립적으로 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 아릴기이다.According to an exemplary embodiment of the present specification, Ar605 and Ar606 are the same as or different from each other, and are each independently a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms. am.
본 명세서의 일 실시상태에 따르면, 상기 Ar605 및 Ar606는 서로 같거나 상이하고, 각각 독립적으로 탄소수 6 내지 30의 단환 또는 다환의 아릴기로 치환 또는 비치환된 페닐기; 또는 바이페닐기이다.According to an exemplary embodiment of the present specification, Ar605 and Ar606 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; Or it is a biphenyl group.
본 명세서의 일 실시상태에 따르면, 상기 Ar605 및 Ar606는 서로 같거나 상이하고, 각각 독립적으로 페닐기, 또는 나프틸기로 치환 또는 비치환된 페닐기; 또는 바이페닐기이다.According to an exemplary embodiment of the present specification, Ar605 and Ar606 are the same as or different from each other, and are each independently a phenyl group or a phenyl group substituted or unsubstituted by a naphthyl group; Or it is a biphenyl group.
본 명세서의 일 실시상태에 따르면, 상기 Ar605 및 Ar606는 바이페닐기이다.According to an exemplary embodiment of the present specification, Ar605 and Ar606 are biphenyl groups.
본 명세서의 일 실시상태에 따르면, 상기 Ar605 및 Ar606는 페닐기이다.According to an exemplary embodiment of the present specification, Ar605 and Ar606 are phenyl groups.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HB-1은 하기 화합물일 수 있으나, 이에만 한정되는 것은 아니다.According to an exemplary embodiment of the present specification, the chemical formula HB-1 may be the following compound, but is not limited thereto.
Figure PCTKR2023004877-appb-img-000052
Figure PCTKR2023004877-appb-img-000052
본 명세서에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present specification may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
본 명세서에 따른 유기 발광 소자는 다양한 전자 장치에 포함되어 사용될 수 있다. 예컨대, 상기 전자 장치는 디스플레이 패널, 터치 패널, 태양광 모듈, 조명 장치 등일 수 있고, 이에 한정되지 않는다.The organic light emitting device according to the present specification can be included and used in various electronic devices. For example, the electronic device may be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.
이하, 본 명세서를 구체적으로 설명하기 위해 실시예 및 비교예 등을 들어 상세하게 설명하기로 한다. 그러나, 본 명세서에 따른 실시예 및 비교예는 여러 가지 다른 형태로 변형될 수 있으며, 본 명세서의 범위가 아래에서 상술하는 실시예 및 비교예에 한정되는 것으로 해석되지 않는다. 본 명세서의 실시예 및 비교예는 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, in order to explain the present specification in detail, examples and comparative examples will be described in detail. However, the Examples and Comparative Examples according to the present specification may be modified in various other forms, and the scope of the present specification is not to be construed as being limited to the Examples and Comparative Examples detailed below. The examples and comparative examples of this specification are provided to more completely explain the present specification to those with average knowledge in the art.
<합성예><Synthesis example>
합성예 1. 화합물 1의 합성Synthesis Example 1. Synthesis of Compound 1
Figure PCTKR2023004877-appb-img-000053
Figure PCTKR2023004877-appb-img-000053
9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol), 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 및 소듐 터트-부톡사이드(6.26 g, 65.13 mmol)에 톨루엔(200 ml)을 가한 후, 10분 동안 가열 교반하였다. 상기 혼합물에 톨루엔(20ml)에 용해시킨 비스(트리-터트-부틸포스핀)팔라듐 (0.12 g, 0.23 mmol)을 가한 후 1시간 동안 가열 교반하였다. 반응 종결 및 여과 후, 톨루엔과 물로 층분리 하였다. 용매 제거 후 에틸아세테이트로 재결정하여 상기 화합물 1 (28.00 g, 78.68 % 수율)을 수득하였다. (MS[M+H]+ = 765)9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol), 4'-(naphthalene-1- 1) - Toluene (200 ml) was added to N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) and sodium tert-butoxide (6.26 g, 65.13 mmol), It was heated and stirred for 10 minutes. Bis(tri-tert-butylphosphine)palladium (0.12 g, 0.23 mmol) dissolved in toluene (20 ml) was added to the mixture, and then heated and stirred for 1 hour. After completion of reaction and filtration. , the layers were separated with toluene and water. After removal of the solvent, recrystallization was performed with ethyl acetate to obtain Compound 1 (28.00 g, 78.68% yield). (MS[M+H]+ = 765)
합성예 2. 화합물 2의 합성Synthesis Example 2. Synthesis of Compound 2
Figure PCTKR2023004877-appb-img-000054
Figure PCTKR2023004877-appb-img-000054
상기 합성예 1에서 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 N-(4'-(나프탈렌-1-일)-[1,1'-비페닐]-4-일)-[1,1'-비페닐]-2-아민 (21.24 g, 47.45 mmol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 2 (30.5 g, 77.95 % 수율)를 수득하였다. (MS[M+H]+ = 841)In Synthesis Example 1, instead of 4'-(naphthalen-1-yl)- N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol), N -(4'-(naphthalene- Synthesis Example 1 above, except that 1-yl)-[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine (21.24 g, 47.45 mmol) was used. Compound 2 (30.5 g, 77.95% yield) was obtained in the same manner as above. (MS[M+H]+ = 841)
합성예 3. 화합물 3의 합성Synthesis Example 3. Synthesis of Compound 3
Figure PCTKR2023004877-appb-img-000055
Figure PCTKR2023004877-appb-img-000055
상기 합성예 1에서 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 N-(4'-(나프탈렌-1-일)-[1,1'-비페닐]-4-일)나프탈렌-1-아민 (20.00 g, 47.45 mmol) 을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 3 (29.5 g, 77.81 % 수율)을 수득하였다. (MS[M+H]+ = 815)In Synthesis Example 1, instead of 4'-(naphthalen-1-yl)- N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol), N -(4'-(naphthalene- Compound 3 (29.5 mmol) was prepared in the same manner as in Synthesis Example 1, except that 1-yl)-[1,1'-biphenyl]-4-yl)naphthalen-1-amine (20.00 g, 47.45 mmol) was used. g, 77.81% yield) was obtained. (MS[M+H]+ = 815)
합성예 4. 화합물 4의 합성Synthesis Example 4. Synthesis of Compound 4
Figure PCTKR2023004877-appb-img-000056
Figure PCTKR2023004877-appb-img-000056
상기 합성예 1에서 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 N-(4'-(나프탈렌-1-일)-[1,1'-비페닐]-4-일)나프탈렌-2-아민 (20.00 g, 47.45 mmol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 4 (29.0 g, 76.49 % 수율)를 수득하였다. (MS[M+H]+ = 815)In Synthesis Example 1, instead of 4'-(naphthalen-1-yl)- N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol), N -(4'-(naphthalene- Compound 4 (29.0%) was prepared in the same manner as in Synthesis Example 1, except that 1-yl)-[1,1'-biphenyl]-4-yl)naphthalen-2-amine (20.00 g, 47.45 mmol) was used. g, 76.49% yield) was obtained. (MS[M+H]+ = 815)
합성예 5. 화합물 5의 합성Synthesis Example 5. Synthesis of Compound 5
Figure PCTKR2023004877-appb-img-000057
Figure PCTKR2023004877-appb-img-000057
상기 합성예 1에서 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 4'-(나프탈렌-2-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 5 (27.5 g, 77.28 % 수율)를 수득하였다. (MS[M+H]+ = 765)In Synthesis Example 1, 4'-(naphthalen-1-yl)- N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) was replaced with 4'-(naphthalen-2-yl) )- N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) was used, and the compound 5 (27.5 g, 77.28% yield) was prepared in the same manner as in Synthesis Example 1. ) was obtained. (MS[M+H]+ = 765)
합성예 6. 화합물 6의 합성Synthesis Example 6. Synthesis of Compound 6
Figure PCTKR2023004877-appb-img-000058
Figure PCTKR2023004877-appb-img-000058
상기 합성예 1에서 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 N-(4'-(나프탈렌-2-일)-[1,1'-비페닐]-4-일)-[1,1'-비페닐]-2-아민 (21.24 g, 47.45 mmol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 6 (30.5 g, 77.95 % 수율)을 수득하였다. (MS[M+H]+ = 841)In Synthesis Example 1, instead of 4'-(naphthalen-1-yl)- N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol), N -(4'-(naphthalene- Synthesis Example 1 above, except that 2-yl)-[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine (21.24 g, 47.45 mmol) was used. Compound 6 (30.5 g, 77.95% yield) was obtained in the same manner as above. (MS[M+H]+ = 841)
합성예 7. 화합물 7의 합성Synthesis Example 7. Synthesis of Compound 7
Figure PCTKR2023004877-appb-img-000059
Figure PCTKR2023004877-appb-img-000059
상기 합성예 1에서 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 3'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 7 (27.0 g, 75.87 % 수율)을 수득하였다. (MS[M+H]+ = 765)In Synthesis Example 1, 3'-(naphthalen-1-yl) was used instead of 4'-(naphthalen-1-yl)- N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol). )- N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) was used, and the compound 7 (27.0 g, 75.87% yield) was prepared in the same manner as in Synthesis Example 1. ) was obtained. (MS[M+H]+ = 765)
합성예 8. 화합물 8의 합성Synthesis Example 8. Synthesis of Compound 8
Figure PCTKR2023004877-appb-img-000060
Figure PCTKR2023004877-appb-img-000060
상기 합성예 1에서 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 2'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 8 (26.5 g, 74.47 % 수율)을 수득하였다. (MS[M+H]+ = 765)In Synthesis Example 1, 2'-(naphthalen-1-yl) was used instead of 4'-(naphthalen-1-yl)- N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol). )- N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) was used, and the compound 8 (26.5 g, 74.47% yield) was prepared in the same manner as in Synthesis Example 1. ) was obtained. (MS[M+H]+ = 765)
합성예 9. 화합물 9의 합성Synthesis Example 9. Synthesis of Compound 9
Figure PCTKR2023004877-appb-img-000061
Figure PCTKR2023004877-appb-img-000061
상기 합성예 1에서 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)대신 9-(4'-클로로-[1,1':3',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 9 (27.5 g, 77.28 % 수율)를 수득하였다. (MS[M+H]+ = 765)In Synthesis Example 1, 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) was used instead of 9-( The same as Synthesis Example 1 except that 4'-chloro-[1,1':3',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) was used. Compound 9 (27.5 g, 77.28% yield) was obtained through this method. (MS[M+H]+ = 765)
합성예 10. 화합물 10의 합성Synthesis Example 10. Synthesis of Compound 10
Figure PCTKR2023004877-appb-img-000062
Figure PCTKR2023004877-appb-img-000062
상기 합성예 1에서 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 9-(4'-클로로-[1,1':3',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 N-(4'-(나프탈렌-1-일)-[1,1'-비페닐]-4-일)-[1,1'-비페닐]-2-아민 (21.24 g, 47.45 mmol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 10 (30.0 g, 76.67 % 수율)을 수득하였다. (MS[M+H]+ = 841)In Synthesis Example 1, 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and 4'- (naphthalen-1-yl) -N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) instead of 9-(4'-chloro-[1,1':3', 1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and N -(4'-(naphthalen-1-yl)-[1,1'-biphenyl]-4 -Y)-[1,1'-biphenyl]-2-amine (21.24 g, 47.45 mmol) was used, and the compound 10 (30.0 g, 76.67% yield) was prepared in the same manner as in Synthesis Example 1. Obtained. (MS[M+H]+ = 841)
합성예 11. 화합물 11의 합성Synthesis Example 11. Synthesis of Compound 11
Figure PCTKR2023004877-appb-img-000063
Figure PCTKR2023004877-appb-img-000063
상기 합성예 1에서 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 9-(4'-클로로-[1,1':3',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 3'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 11 (27.5 g, 77.28 % 수율)을 수득하였다. (MS[M+H]+ = 765)In Synthesis Example 1, 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and 4'- (naphthalen-1-yl) -N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) instead of 9-(4'-chloro-[1,1':3', 1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) with 3'-(naphthalen-1-yl) -N -phenyl-[1,1'-biphenyl]- Compound 11 (27.5 g, 77.28% yield) was obtained in the same manner as in Synthesis Example 1, except that 4-amine (17.63 g, 47.45 mmol) was used. (MS[M+H]+ = 765)
합성예 12. 화합물 12의 합성Synthesis Example 12. Synthesis of Compound 12
Figure PCTKR2023004877-appb-img-000064
Figure PCTKR2023004877-appb-img-000064
상기 합성예 1에서 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 9-(4'-클로로-[1,1':3',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 2'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 12 (26.5 g, 74.47 % 수율)를 수득하였다. (MS[M+H]+ = 765)In Synthesis Example 1, 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and 4'- (naphthalen-1-yl) -N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) instead of 9-(4'-chloro-[1,1':3', 1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) with 2'-(naphthalen-1-yl) -N -phenyl-[1,1'-biphenyl]- Compound 12 (26.5 g, 74.47% yield) was obtained in the same manner as in Synthesis Example 1, except that 4-amine (17.63 g, 47.45 mmol) was used. (MS[M+H]+ = 765)
합성예 13. 화합물 13의 합성Synthesis Example 13. Synthesis of Compound 13
Figure PCTKR2023004877-appb-img-000065
Figure PCTKR2023004877-appb-img-000065
상기 합성예 1에서 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 9-(4'-클로로-[1,1':3',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 4'-(나프탈렌-2-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 13 (27.5 g, 77.28 % 수율)을 수득하였다. (MS[M+H]+ = 765)In Synthesis Example 1, 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and 4'- (naphthalen-1-yl) -N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) instead of 9-(4'-chloro-[1,1':3', 1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) with 4'-(naphthalen-2-yl) -N -phenyl-[1,1'-biphenyl]- Compound 13 (27.5 g, 77.28% yield) was obtained in the same manner as in Synthesis Example 1, except that 4-amine (17.63 g, 47.45 mmol) was used. (MS[M+H]+ = 765)
합성예 14. 화합물 14의 합성Synthesis Example 14. Synthesis of Compound 14
Figure PCTKR2023004877-appb-img-000066
Figure PCTKR2023004877-appb-img-000066
상기 합성예 1에서 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 9-(4'-클로로-[1,1':3',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 N-(4'-(나프탈렌-2-일)-[1,1'-비페닐]-4-일)-[1,1'-비페닐]-2-아민 (21.24 g, 47.45 mmol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 14 (30.5 g, 77.95 % 수율)를 수득하였다. (MS[M+H]+ = 841)In Synthesis Example 1, 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and 4'- (naphthalen-1-yl) -N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) instead of 9-(4'-chloro-[1,1':3', 1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and N -(4'-(naphthalen-2-yl)-[1,1'-biphenyl]-4 -Y)-[1,1'-biphenyl]-2-amine (21.24 g, 47.45 mmol) was used, and the compound 14 (30.5 g, 77.95% yield) was prepared in the same manner as in Synthesis Example 1. Obtained. (MS[M+H]+ = 841)
합성예 15. 화합물 15의 합성Synthesis Example 15. Synthesis of Compound 15
Figure PCTKR2023004877-appb-img-000067
Figure PCTKR2023004877-appb-img-000067
상기 합성예 1에서 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 N-페닐-4-(4-페닐나프탈렌-1-일)아닐린 (17.63 g, 47.45 mmol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 15 (28.0 g, 78.68 % 수율)를 수득하였다. (MS[M+H]+ = 765)In Synthesis Example 1, 4'-(naphthalen-1-yl)- N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) was used instead of N -phenyl-4-(4- Compound 15 (28.0 g, 78.68% yield) was obtained in the same manner as in Synthesis Example 1, except that phenylnaphthalen-1-yl)aniline (17.63 g, 47.45 mmol) was used. (MS[M+H]+ = 765)
합성예 16. 화합물 16의 합성Synthesis Example 16. Synthesis of Compound 16
Figure PCTKR2023004877-appb-img-000068
Figure PCTKR2023004877-appb-img-000068
상기 합성예 1에서 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 N-(4-(4-페닐나프탈렌-1-일)페닐)-[1,1'-비페닐]-2-아민 (21.24 g, 47.45 mmol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 16 (30.5 g, 77.95 % 수율)을 수득하였다. (MS[M+H]+ = 841)In Synthesis Example 1, instead of 4'-(naphthalen-1-yl)- N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol), N -(4-(4-phenyl) Compound 16 (30.5 g, 77.95% yield) was obtained. (MS[M+H]+ = 841)
합성예 17. 화합물 17의 합성Synthesis Example 17. Synthesis of Compound 17
Figure PCTKR2023004877-appb-img-000069
Figure PCTKR2023004877-appb-img-000069
상기 합성예 1에서 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 N-페닐-4-(2-페닐나프탈렌-1-일)아닐린 (17.63 g, 47.45 mmol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 17 (27.0 g, 75.87 % 수율)을 수득하였다. (MS[M+H]+ = 765)In Synthesis Example 1, 4'-(naphthalen-1-yl)- N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) was used instead of N -phenyl-4-(2- Compound 17 (27.0 g, 75.87% yield) was obtained in the same manner as in Synthesis Example 1, except that phenylnaphthalen-1-yl)aniline (17.63 g, 47.45 mmol) was used. (MS[M+H]+ = 765)
합성예 18. 화합물 18의 합성Synthesis Example 18. Synthesis of Compound 18
Figure PCTKR2023004877-appb-img-000070
Figure PCTKR2023004877-appb-img-000070
상기 합성예 1에서 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 9-(4'-클로로-[1,1':3',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 N-페닐-4-(4-페닐나프탈렌-1-일)아닐린 (17.63 g, 47.45 mmol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 18 (28.0 g, 78.68 % 수율)을 수득하였다. (MS[M+H]+ = 765)In Synthesis Example 1, 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and 4'- (naphthalen-1-yl) -N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) instead of 9-(4'-chloro-[1,1':3', 1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and N -phenyl-4-(4-phenylnaphthalen-1-yl)aniline (17.63 g, 47.45 mmol) Compound 18 (28.0 g, 78.68% yield) was obtained in the same manner as in Synthesis Example 1 except that it was used. (MS[M+H]+ = 765)
합성예 19. 화합물 19의 합성Synthesis Example 19. Synthesis of Compound 19
Figure PCTKR2023004877-appb-img-000071
Figure PCTKR2023004877-appb-img-000071
상기 합성예 1에서 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 9-(4'-클로로-[1,1':3',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 N-(4-(4-페닐나프탈렌-1-일)페닐)-[1,1'-비페닐]-2-아민 (21.24 g, 47.45 mmol) 을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 19 (30.5 g, 77.95 % 수율)를 수득하였다. (MS[M+H]+ = 841)In Synthesis Example 1, 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and 4'- (naphthalen-1-yl) -N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) instead of 9-(4'-chloro-[1,1':3', 1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) with N -(4-(4-phenylnaphthalen-1-yl)phenyl)-[1,1'-ratio Compound 19 (30.5 g, 77.95% yield) was obtained in the same manner as in Synthesis Example 1, except that phenyl]-2-amine (21.24 g, 47.45 mmol) was used. (MS[M+H]+ = 841)
합성예 20. 화합물 20의 합성Synthesis Example 20. Synthesis of Compound 20
Figure PCTKR2023004877-appb-img-000072
Figure PCTKR2023004877-appb-img-000072
상기 합성예 1에서 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 2-(4'-클로로-[1,1',3',1"-터페닐]-3-일)트리페닐렌 (20.00 g, 40.73 mmol)과 N-페닐-[1,1'-비페닐]-4-아민 (10.19 g, 41.55 mmol) 을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 20 (22.50 g, 78.93 % 수율)을 수득하였다. (MS[M+H]+ = 765)In Synthesis Example 1, 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and 4'- (naphthalen-1-yl) -N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) instead of 2-(4'-chloro-[1,1',3', Except for the use of 1"-terphenyl]-3-yl)triphenylene (20.00 g, 40.73 mmol) and N -phenyl-[1,1'-biphenyl]-4-amine (10.19 g, 41.55 mmol) Then, the compound 20 (22.50 g, 78.93% yield) was obtained in the same manner as in Synthesis Example 1. (MS[M+H]+ = 765)
합성예 21. 화합물 21의 합성Synthesis Example 21. Synthesis of Compound 21
Figure PCTKR2023004877-appb-img-000073
Figure PCTKR2023004877-appb-img-000073
상기 합성예 1에서 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 4-([1,1'-비페닐]-4-일)-N-페닐나프탈렌-1-아민 (17.63 g, 47.45 mmol) 을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 21 (27.5 g, 77.28 % 수율)을 수득하였다. (MS[M+H]+ = 765)In Synthesis Example 1, 4 -([1,1'- Biphenyl]-4-yl)- N -phenylnaphthalen-1-amine (17.63 g, 47.45 mmol) was used, and the compound 21 (27.5 g, 77.28% yield) was prepared in the same manner as in Synthesis Example 1. Obtained. (MS[M+H]+ = 765)
합성예 22. 화합물 22의 합성Synthesis Example 22. Synthesis of Compound 22
Figure PCTKR2023004877-appb-img-000074
Figure PCTKR2023004877-appb-img-000074
상기 합성예 1에서 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 9-(4'-클로로-[1,1':3',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 4-([1,1'-비페닐]-4-일)-N-페닐나프탈렌-1-아민 (17.63 g, 47.45 mmol) 을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 22 (27.5 g, 77.28 % 수율)를 수득하였다. (MS[M+H]+ = 765)In Synthesis Example 1, 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and 4'- (naphthalen-1-yl) -N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) instead of 9-(4'-chloro-[1,1':3', 1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and 4-([1,1'-biphenyl]-4-yl)- N -phenylnaphthalene-1- Compound 22 (27.5 g, 77.28% yield) was obtained in the same manner as in Synthesis Example 1, except that amine (17.63 g, 47.45 mmol) was used. (MS[M+H]+ = 765)
합성예 23. 화합물 23의 합성Synthesis Example 23. Synthesis of Compound 23
Figure PCTKR2023004877-appb-img-000075
Figure PCTKR2023004877-appb-img-000075
상기 합성예 1에서 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 7-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-7H-벤조[c]카바졸 (20.00 g, 41.67 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (15.79 g, 42.50 mmol) 을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 23 (26.5 g, 78.03 % 수율)을 수득하였다. (MS[M+H]+ = 815)In Synthesis Example 1, 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and 4'- (naphthalen-1-yl)- N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) instead of 7-(4'-chloro-[1,1':2', 1"-terphenyl]-2-yl)-7 H -benzo[ c ]carbazole (20.00 g, 41.67 mmol) and 4'-(naphthalen-1-yl) -N -phenyl-[1,1'- Compound 23 (26.5 g, 78.03% yield) was obtained in the same manner as in Synthesis Example 1, except that biphenyl]-4-amine (15.79 g, 42.50 mmol) was used. (MS[M+H]+ = 815)
합성예 24. 화합물 24의 합성Synthesis Example 24. Synthesis of Compound 24
Figure PCTKR2023004877-appb-img-000076
Figure PCTKR2023004877-appb-img-000076
상기 합성예 1에서 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 5-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-5H-벤조[b]카바졸 (20.00 g, 41.67 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (15.79 g, 42.50 mmol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 24 (26.0 g, 76.56 % 수율)를 수득하였다. (MS[M+H]+ = 815)In Synthesis Example 1, 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and 4'- (naphthalen-1-yl) -N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) instead of 5-(4'-chloro-[1,1':2', 1"-terphenyl]-2-yl)-5 H -benzo[ b ]carbazole (20.00 g, 41.67 mmol) and 4'-(naphthalen-1-yl) -N -phenyl-[1,1'- Compound 24 (26.0 g, 76.56% yield) was obtained in the same manner as in Synthesis Example 1, except that biphenyl]-4-amine (15.79 g, 42.50 mmol) was used. (MS[M+H]+ = 815)
합성예 25. 화합물 25의 합성Synthesis Example 25. Synthesis of Compound 25
Figure PCTKR2023004877-appb-img-000077
Figure PCTKR2023004877-appb-img-000077
상기 합성예 1에서 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 7-(4'-클로로-[1,1':3',1"-터페닐]-2-일)-7H-벤조[c]카바졸 (20.00 g, 41.67 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (15.79 g, 42.50 mmol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 25 (26.5 g, 78.03 % 수율)를 수득하였다. (MS[M+H]+ = 815)In Synthesis Example 1, 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and 4'- (naphthalen-1-yl) -N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) instead of 7-(4'-chloro-[1,1':3', 1"-terphenyl]-2-yl)-7 H -benzo[ c ]carbazole (20.00 g, 41.67 mmol) and 4'-(naphthalen-1-yl) -N -phenyl-[1,1'- Compound 25 (26.5 g, 78.03% yield) was obtained in the same manner as in Synthesis Example 1, except that biphenyl]-4-amine (15.79 g, 42.50 mmol) was used. (MS[M+H]+ = 815)
합성예 26. 화합물 26의 합성Synthesis Example 26. Synthesis of Compound 26
Figure PCTKR2023004877-appb-img-000078
Figure PCTKR2023004877-appb-img-000078
상기 합성예 1에서 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 5-(4'-클로로-[1,1':3',1"-터페닐]-2-일)-5H-벤조[b]카바졸 (20.00 g, 41.67 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (15.79 g, 42.50 mmol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 26 (26.5 g, 78.03 % 수율)을 수득하였다. (MS[M+H]+ = 815)In Synthesis Example 1, 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and 4'- (naphthalen-1-yl) -N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) instead of 5-(4'-chloro-[1,1':3', 1"-terphenyl]-2-yl)-5 H -benzo[ b ]carbazole (20.00 g, 41.67 mmol) and 4'-(naphthalen-1-yl) -N -phenyl-[1,1'- Compound 26 (26.5 g, 78.03% yield) was obtained in the same manner as in Synthesis Example 1, except that biphenyl]-4-amine (15.79 g, 42.50 mmol) was used. (MS[M+H]+ = 815)
합성예 27. 화합물 27의 합성Synthesis Example 27. Synthesis of Compound 27
Figure PCTKR2023004877-appb-img-000079
Figure PCTKR2023004877-appb-img-000079
상기 합성예 1에서 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-2-페닐-9H-카바졸 (20.00 g, 39.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (14.98 g, 40.31 mmol) 을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 27 (25.5 g, 76.72 % 수율)을 수득하였다. (MS[M+H]+ = 841)In Synthesis Example 1, 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and 4'- (naphthalen-1-yl) -N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) instead of 9-(4'-chloro-[1,1':2', 1"-terphenyl]-2-yl)-2-phenyl-9 H -carbazole (20.00 g, 39.52 mmol) with 4'-(naphthalen-1-yl) -N -phenyl-[1,1'- Compound 27 (25.5 g, 76.72% yield) was obtained in the same manner as in Synthesis Example 1, except that biphenyl]-4-amine (14.98 g, 40.31 mmol) was used. (MS[M+H]+ = 841)
합성예 28. 화합물 28의 합성Synthesis Example 28. Synthesis of Compound 28
Figure PCTKR2023004877-appb-img-000080
Figure PCTKR2023004877-appb-img-000080
상기 합성예 1에서 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 9-(4'-클로로-[1,1':3',1"-터페닐]-2-일)-2-페닐-9H-카바졸 (20.00 g, 39.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (14.98 g, 40.31 mmol) 을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 28 (25.5 g, 76.72 % 수율)을 수득하였다. (MS[M+H]+ = 841)In Synthesis Example 1, 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and 4'- (naphthalen-1-yl) -N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) instead of 9-(4'-chloro-[1,1':3', 1"-terphenyl]-2-yl)-2-phenyl-9 H -carbazole (20.00 g, 39.52 mmol) with 4'-(naphthalen-1-yl) -N -phenyl-[1,1'- Compound 28 (25.5 g, 76.72% yield) was obtained in the same manner as in Synthesis Example 1, except that biphenyl]-4-amine (14.98 g, 40.31 mmol) was used. (MS[M+H]+ = 841)
합성예 29. 화합물 29의 합성Synthesis Example 29. Synthesis of Compound 29
Figure PCTKR2023004877-appb-img-000081
Figure PCTKR2023004877-appb-img-000081
상기 합성예 1에서 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-3-페닐-9H-카바졸 (20.00 g, 39.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (14.98 g, 40.31 mmol) 을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 29 (26.0 g, 78.22 % 수율)를 수득하였다. (MS[M+H]+ = 841)In Synthesis Example 1, 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and 4'- (naphthalen-1-yl) -N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) instead of 9-(4'-chloro-[1,1':2', 1"-terphenyl]-2-yl)-3-phenyl-9 H -carbazole (20.00 g, 39.52 mmol) with 4'-(naphthalen-1-yl) -N -phenyl-[1,1'- Compound 29 (26.0 g, 78.22% yield) was obtained in the same manner as in Synthesis Example 1, except that biphenyl]-4-amine (14.98 g, 40.31 mmol) was used. (MS[M+H]+ = 841)
합성예 30. 화합물 30의 합성Synthesis Example 30. Synthesis of Compound 30
Figure PCTKR2023004877-appb-img-000082
Figure PCTKR2023004877-appb-img-000082
상기 합성예 1에서 9-(4'-클로로-[1,1':2',1"-터페닐]-2-일)-9H-카바졸 (20.00 g, 46.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 9-(4'-클로로-[1,1':3',1"-터페닐]-2-일)-3-페닐-9H-카바졸 (20.00 g, 39.52 mmol)과 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (14.98 g, 40.31 mmol) 을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 30 (26.0 g, 78.22 % 수율)을 수득하였다. (MS[M+H]+ = 841)In Synthesis Example 1, 9-(4'-chloro-[1,1':2',1"-terphenyl]-2-yl)-9 H -carbazole (20.00 g, 46.52 mmol) and 4'- (naphthalen-1-yl) -N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol) instead of 9-(4'-chloro-[1,1':3', 1"-terphenyl]-2-yl)-3-phenyl-9 H -carbazole (20.00 g, 39.52 mmol) with 4'-(naphthalen-1-yl) -N -phenyl-[1,1'- Compound 30 (26.0 g, 78.22% yield) was obtained in the same manner as in Synthesis Example 1, except that biphenyl]-4-amine (14.98 g, 40.31 mmol) was used. (MS[M+H]+ = 841)
합성예 31. 화합물 31의 합성Synthesis Example 31. Synthesis of Compound 31
Figure PCTKR2023004877-appb-img-000083
Figure PCTKR2023004877-appb-img-000083
상기 합성예 1에서 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 N-(3'-(나프탈렌-1-일)-[1,1'-비페닐]-4-일)나프탈렌-1-아민 (20.00 g, 47.45 mmol) 을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 31 (29.5 g, 77.81 % 수율)을 수득하였다. (MS[M+H]+ = 815)In Synthesis Example 1, instead of 4'-(naphthalen-1-yl)- N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol), N -(3'-(naphthalene- Compound 31 (29.5 mmol) was prepared in the same manner as in Synthesis Example 1, except that 1-yl)-[1,1'-biphenyl]-4-yl)naphthalen-1-amine (20.00 g, 47.45 mmol) was used. g, 77.81% yield) was obtained. (MS[M+H]+ = 815)
합성예 32. 화합물 32의 합성Synthesis Example 32. Synthesis of Compound 32
Figure PCTKR2023004877-appb-img-000084
Figure PCTKR2023004877-appb-img-000084
상기 합성예 1에서 4'-(나프탈렌-1-일)-N-페닐-[1,1'-비페닐]-4-아민 (17.63 g, 47.45 mmol) 대신 N-(2'-(나프탈렌-1-일)-[1,1'-비페닐]-4-일)-[1,1'-비페닐]-2-아민 (21.24 g, 47.45 mol)을 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 상기 화합물 32 (30.5 g, 77.95 % 수율)를 수득하였다. (MS[M+H]+ = 841)In Synthesis Example 1, instead of 4'-(naphthalen-1-yl)- N -phenyl-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol), N -(2'-(naphthalene- Synthesis Example 1 above, except that 1-yl)-[1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine (21.24 g, 47.45 mol) was used. Compound 32 (30.5 g, 77.95% yield) was obtained in the same manner as above. (MS[M+H]+ = 841)
<실험예 및 비교 실험예><Experimental examples and comparative experimental examples>
실험예 1-1Experimental Example 1-1
ITO(Indium Tin Oxide)가 1,400Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with a thin film of ITO (Indium Tin Oxide) with a thickness of 1,400 Å was placed in distilled water with a detergent dissolved in it and washed ultrasonically. At this time, a detergent manufactured by Fischer Co. was used, and distilled water filtered secondarily using a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum evaporator.
이렇게 준비된 ITO 투명 전극 위에 하기 화합물 HAT을 100Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 그 위에 정공수송층으로 하기 화합물 HT1을 1150Å 두께로 진공 증착한 후, 전자차단층으로 상기 합성예 1에서 제조된 화합물 1을 150Å의 두께로 열 진공 증착하였다. 이어서, 발광층으로 하기 화합물 BH 및 하기 화합물 BD을 25:1의 중량비로 200Å의 두께로 진공 증착하였다. 이어서, 정공차단층으로 하기 화합물 HB1을 50Å의 두께로 진공 증착하였다. 이어서, 전자 주입 및 수송층으로 하기 화합물 ET1과 하기 화합물 LiQ을 1:1의 중량비로 310Å의 두께로 열 진공 증착하였다. 상기 전자 주입 및 수송층 위에 순차적으로 12Å의 두께로 리튬플로라이드(LiF)와 1000Å 두께로 알루미늄을 증착하여 음극을 형성하여, 유기 발광 소자를 제조하였다.On the ITO transparent electrode prepared in this way, the following compound HAT was thermally vacuum deposited to a thickness of 100 Å to form a hole injection layer. The following compound HT1 was vacuum deposited to a thickness of 1150 Å as a hole transport layer thereon, and then Compound 1 prepared in Synthesis Example 1 was thermally vacuum deposited to a thickness of 150 Å as an electron blocking layer. Next, the following compound BH and the following compound BD were vacuum deposited to a thickness of 200 Å at a weight ratio of 25:1 as an emitting layer. Next, the following compound HB1 was vacuum deposited to a thickness of 50 Å as a hole blocking layer. Next, as an electron injection and transport layer, the following compound ET1 and the following compound LiQ were thermally vacuum deposited to a thickness of 310 Å at a weight ratio of 1:1. Lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1000 Å were sequentially deposited on the electron injection and transport layer to form a cathode, thereby manufacturing an organic light-emitting device.
Figure PCTKR2023004877-appb-img-000085
Figure PCTKR2023004877-appb-img-000085
실험예 1-2 내지 1-32 및 비교 실험예 1-1 내지 1-3Experimental Examples 1-2 to 1-32 and Comparative Experimental Examples 1-1 to 1-3
상기 실험예 1-1에서 화합물 1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실험예 1-1과 동일한 방법으로 실험예 1-2 내지 1-32 및 비교 실험예 1-1 내지 1-3의 유기 발광 소자를 제작하였다.Experimental Examples 1-2 to 1-32 and Comparative Experimental Example 1-1 were conducted in the same manner as Experimental Example 1-1, except that the compounds listed in Table 1 below were used instead of Compound 1 in Experimental Example 1-1. The organic light emitting devices of 1-3 to 1 were manufactured.
Figure PCTKR2023004877-appb-img-000086
Figure PCTKR2023004877-appb-img-000086
실험예 및 비교 실험예에서 제조한 유기 발광 소자에 10 mA/cm2의 전류를 인가하였을 때, 전압, 효율, 색좌표 및 수명을 측정하고 그 결과를 하기 표 1에 나타내었다. 한편, T95는 휘도가 초기 휘도(6000 nit)에서 95%로 감소되는 데 소요되는 시간을 의미한다. Experimental Examples and Comparisons When a current of 10 mA/cm 2 was applied to the organic light-emitting device manufactured in the experimental example, the voltage, efficiency, color coordinate, and lifespan were measured, and the results are shown in Table 1 below. Meanwhile, T95 refers to the time it takes for the luminance to decrease from the initial luminance (6000 nit) to 95%.
전자차단층Electronic blocking layer 전압 (V @ 10mA/cm2)Voltage (V @ 10mA/cm 2 ) 효율(cd/A @ 10mA/cm2)Efficiency (cd/A @ 10mA/cm 2 ) 색좌표 (x, y)Color coordinates (x, y) 수명
(T95, hr)life span
(T95, hr)
실험예 1-1Experimental Example 1-1 화합물 1Compound 1 3.543.54 5.925.92 0.140, 0.0430.140, 0.043 195195
실험예 1-2Experimental Example 1-2 화합물 2compound 2 3.563.56 5.945.94 0.140, 0.0430.140, 0.043 190190
실험예 1-3Experimental Example 1-3 화합물 3Compound 3 3.563.56 5.935.93 0.141, 0.0430.141, 0.043 180180
실험예 1-4Experimental Example 1-4 화합물 4Compound 4 3.553.55 5.885.88 0.141, 0.0440.141, 0.044 185185
실험예 1-5Experimental Example 1-5 화합물 5Compound 5 3.543.54 5.885.88 0.140, 0.0440.140, 0.044 190190
실험예 1-6Experimental Example 1-6 화합물 6Compound 6 3.553.55 5.905.90 0.140, 0.0440.140, 0.044 190190
실험예 1-7Experimental Example 1-7 화합물 7Compound 7 3.563.56 5.925.92 0.140, 0.0430.140, 0.043 190190
실험예 1-8Experimental Example 1-8 화합물 8Compound 8 3.573.57 5.935.93 0.140, 0.0430.140, 0.043 190190
실험예 1-9Experimental Example 1-9 화합물 9Compound 9 3.543.54 5.915.91 0.141, 0.0440.141, 0.044 195195
실험예 1-10Experimental Example 1-10 화합물 10Compound 10 3.553.55 5.925.92 0.141, 0.0430.141, 0.043 190190
실험예 1-11Experimental Example 1-11 화합물 11Compound 11 3.573.57 5.925.92 0.140, 0.0440.140, 0.044 185185
실험예 1-12Experimental Example 1-12 화합물 12Compound 12 3.563.56 5.925.92 0.140, 0.0440.140, 0.044 185185
실험예 1-13Experimental Example 1-13 화합물 13Compound 13 3.543.54 5.875.87 0.141, 0.0440.141, 0.044 190190
실험예 1-14Experimental Example 1-14 화합물 14Compound 14 3.543.54 5.885.88 0.141, 0.0440.141, 0.044 185185
실험예 1-15Experimental Example 1-15 화합물 15Compound 15 3.553.55 5.935.93 0.140, 0.0430.140, 0.043 190190
실험예 1-16Experimental Example 1-16 화합물 16Compound 16 3.563.56 5.955.95 0.140, 0.0430.140, 0.043 185185
실험예 1-17Experimental Example 1-17 화합물 17Compound 17 3.543.54 5.915.91 0.141, 0.0430.141, 0.043 185185
실험예 1-18Experimental Example 1-18 화합물 18Compound 18 3.543.54 5.915.91 0.141, 0.0430.141, 0.043 185185
실험예 1-19Experimental Example 1-19 화합물 19Compound 19 3.553.55 5.915.91 0.141, 0.0440.141, 0.044 185185
실험예 1-20Experimental Example 1-20 화합물 20Compound 20 3.553.55 5.905.90 0.140, 0.0440.140, 0.044 185185
실험예 1-21Experimental Example 1-21 화합물 21Compound 21 3.563.56 5.945.94 0.140, 0.0430.140, 0.043 185185
실험예 1-22Experimental Example 1-22 화합물 22Compound 22 3.573.57 5.925.92 0.140, 0.0430.140, 0.043 190190
실험예 1-23Experimental Example 1-23 화합물 23Compound 23 3.543.54 5.905.90 0.140, 0.0440.140, 0.044 185185
실험예 1-24Experimental Example 1-24 화합물 24Compound 24 3.553.55 5.895.89 0.140, 0.0430.140, 0.043 180180
실험예 1-25Experimental Example 1-25 화합물 25Compound 25 3.543.54 5.905.90 0.140, 0.0440.140, 0.044 180180
실험예 1-26Experimental Example 1-26 화합물 26Compound 26 3.543.54 5.905.90 0.141, 0.0430.141, 0.043 185185
실험예 1-27Experimental Example 1-27 화합물 27Compound 27 3.563.56 5.905.90 0.140, 0.0430.140, 0.043 180180
실험예 1-28Experimental Example 1-28 화합물 28Compound 28 3.563.56 5.895.89 0.140, 0.0430.140, 0.043 185185
실험예 1-29Experimental Example 1-29 화합물 29Compound 29 3.573.57 5.895.89 0.140, 0.0430.140, 0.043 180180
실험예 1-30Experimental Example 1-30 화합물 30Compound 30 3.563.56 5.905.90 0.141, 0.0430.141, 0.043 185185
실험예 1-31Experimental Example 1-31 화합물 31Compound 31 3.583.58 5.945.94 0.140, 0.0430.140, 0.043 185185
실험예 1-32Experimental Example 1-32 화합물 32Compound 32 3.583.58 5.925.92 0.140, 0.0430.140, 0.043 180180
비교 실험예 1-1Comparative Experiment Example 1-1 EB1EB1 3.803.80 5.205.20 0.144, 0.0480.144, 0.048 130130
비교 실험예 1-2Comparative Experiment Example 1-2 EB2EB2 3.853.85 5.225.22 0.145, 0.0490.145, 0.049 125125
비교 실험예 1-3Comparative Experiment Example 1-3 EB3EB3 3.873.87 5.155.15 0.144, 0.0480.144, 0.048 115115
실험예 2-1 내지 2-14 및 비교 실험예 2-1 내지 2-3Experimental Examples 2-1 to 2-14 and Comparative Experimental Examples 2-1 to 2-3
상기 실험예 1-1에서 전자차단층으로 상기 화합물 1 대신 상기 화합물 EB1을 사용하고, 정공수송층으로 상기 화합물 HT1 대신 하기 표 2에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실험예 1-1과 동일한 방법으로 실험예 2-1 내지 2-14 및 비교 실험예 2-1 내지 2-3의 유기 발광 소자를 제작하였다.In Experimental Example 1-1, except that the compound EB1 was used as the electron blocking layer instead of the compound 1, and the compound shown in Table 2 below was used as the hole transport layer instead of the compound HT1. The organic light-emitting devices of Experimental Examples 2-1 to 2-14 and Comparative Experimental Examples 2-1 to 2-3 were manufactured in the same manner.
Figure PCTKR2023004877-appb-img-000087
Figure PCTKR2023004877-appb-img-000087
실험예 및 비교 실험예에서 제조한 유기 발광 소자에 10 mA/cm2의 전류를 인가하였을 때, 전압, 효율, 색좌표 및 수명을 측정하고 그 결과를 하기 표 2에 나타내었다. 한편, T95는 휘도가 초기 휘도(6000 nit)에서 95%로 감소되는 데 소요되는 시간을 의미한다.Experimental Examples and Comparisons When a current of 10 mA/cm 2 was applied to the organic light-emitting device manufactured in the experimental example, the voltage, efficiency, color coordinate, and lifespan were measured, and the results are shown in Table 2 below. Meanwhile, T95 refers to the time it takes for the luminance to decrease from the initial luminance (6000 nit) to 95%.
정공수송층hole transport layer 전압 (V @ 10mA/cm2)Voltage (V @ 10mA/cm 2 ) 효율(cd/A @ 10mA/cm2)Efficiency (cd/A @ 10mA/cm 2 ) 색좌표 (x, y)Color coordinates (x, y) 수명
(T95, hr)life span
(T95, hr)
실험예 2-1Experimental Example 2-1 화합물 1 Compound 1 3.583.58 5.885.88 0.140, 0.0430.140, 0.043 190190
실험예 2-2Experimental Example 2-2 화합물 5 Compound 5 3.573.57 5.855.85 0.140, 0.0440.140, 0.044 190190
실험예 2-3Experimental Example 2-3 화합물 6 Compound 6 3.583.58 5.865.86 0.141, 0.0430.141, 0.043 185185
실험예 2-4Experimental Example 2-4 화합물 9 Compound 9 3.573.57 5.875.87 0.140, 0.0430.140, 0.043 185185
실험예 2-5Experimental Example 2-5 화합물 13Compound 13 3.573.57 5.855.85 0.140, 0.0430.140, 0.043 190190
실험예 2-6Experimental Example 2-6 화합물 14Compound 14 3.583.58 5.865.86 0.140, 0.0430.140, 0.043 190190
실험예 2-7Experimental Example 2-7 화합물 15Compound 15 3.603.60 5.895.89 0.140, 0.0440.140, 0.044 185185
실험예 2-8Experimental Example 2-8 화합물 18Compound 18 3.583.58 5.885.88 0.140, 0.0440.140, 0.044 185185
실험예 2-9Experimental Example 2-9 화합물 23Compound 23 3.573.57 5.885.88 0.140, 0.0430.140, 0.043 185185
실험예 2-10Experimental Example 2-10 화합물 24Compound 24 3.583.58 5.875.87 0.140, 0.0430.140, 0.043 180180
실험예 2-11Experimental Example 2-11 화합물 25Compound 25 3.583.58 5.865.86 0.140, 0.0430.140, 0.043 185185
실험예 2-12Experimental Example 2-12 화합물 26Compound 26 3.583.58 5.865.86 0.140, 0.0440.140, 0.044 185185
실험예 2-13Experimental Example 2-13 화합물 29Compound 29 3.583.58 5.855.85 0.140, 0.0430.140, 0.043 180180
실험예 2-14Experimental Example 2-14 화합물 30Compound 30 3.573.57 5.855.85 0.140, 0.0440.140, 0.044 180180
비교 실험예 1-1Comparative Experiment Example 1-1 HT1HT1 3.803.80 5.205.20 0.144, 0.0480.144, 0.048 130130
비교 실험예 2-1Comparative Experiment Example 2-1 HT2HT2 3.783.78 5.155.15 0.144, 0.0480.144, 0.048 120120
비교 실험예 2-2Comparative Experiment Example 2-2 HT3HT3 3.703.70 5.125.12 0.145, 0.0480.145, 0.048 125125
비교 실험예 2-3Comparative Experiment Example 2-3 HT4HT4 3.743.74 5.085.08 0.144, 0.0490.144, 0.049 110110
상기 표 1 및 2에 나타난 바와 같이, 본 명세서의 일 실시상태에 따른 화학식 1의 화합물은 전자 차단 능력 또는 정공 수송 능력이 우수하여 이를 전자차단층 또는 정공수송층으로 사용한 유기 발광 소자는 구동 전압, 효율 및 수명 면에서 현저한 효과를 나타내는 것으로 확인되었다. As shown in Tables 1 and 2 above, the compound of Formula 1 according to an exemplary embodiment of the present specification has excellent electron blocking ability or hole transport ability, and an organic light emitting device using it as an electron blocking layer or hole transport layer has a driving voltage and efficiency. It was confirmed to have a significant effect in terms of lifespan and longevity.
구체적으로, 본 명세서의 일 실시상태에 따른 화학식 1의 화합물은 벤젠고리에 카바졸이 오쏘(ortho) 위치로 치환되는 구조로써, 메타(meta)나 파라(para) 위치로 치환되는 구조보다 컨쥬게이션이 끊어져 있는 상태이고, R4 위치에 수소 이외의 치환기를 가지므로, 컨쥬게이션 길이를 조절함으로써 HOMO 및 LUMO 레벨을 조절하기 쉬운 구조이다. Specifically, the compound of Formula 1 according to an exemplary embodiment of the present specification has a structure in which carbazole is substituted in the ortho position on the benzene ring, and is more effective in conjugation than the structure in which carbazole is substituted in the meta or para position. Since it is in a broken state and has a substituent other than hydrogen at the R4 position, it is a structure that makes it easy to control the HOMO and LUMO levels by adjusting the conjugation length.
본 명세서의 일 실시상태에 따른 화학식 1의 화합물을 적용한 유기 발광 소자인 실험예 1-1 내지 1-32 및 2-1 내지 2-14은 본 명세서의 화학식 1의 R4위치가 수소인 화합물을 적용한 유기 발광 소자인 비교 실험예 1-1 내지 1-3 및 2-1 내지 2-3 보다 구동 전압, 효율 및 수명 면에서 현저한 효과를 나타내는 것을 확인하였다.Experimental Examples 1-1 to 1-32 and 2-1 to 2-14, which are organic light-emitting devices using the compound of Formula 1 according to an embodiment of the present specification, are obtained by applying the compound in which the R4 position of Formula 1 of the present specification is hydrogen. It was confirmed that the organic light emitting device showed a significant effect in terms of driving voltage, efficiency, and lifespan compared to Comparative Experimental Examples 1-1 to 1-3 and 2-1 to 2-3.

Claims (11)

  1. 하기 화학식 1의 화합물:Compound of formula 1:
    [화학식 1][Formula 1]
    Figure PCTKR2023004877-appb-img-000088
    Figure PCTKR2023004877-appb-img-000088
    상기 화학식 1에 있어서,In Formula 1,
    Ar1은 수소; 중수소; 또는 치환 또는 비치환된 단환의 아릴기이고,Ar1 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted monocyclic aryl group,
    R1 내지 R3 및 R5는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 어느 한쌍 이상은 서로 결합하여 치환 또는 비치환된 고리를 형성하며,R1 to R3 and R5 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or one or more adjacent pairs are combined with each other to form a substituted or unsubstituted ring,
    R4는 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이거나, 인접한 어느 한 쌍 이상은 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R4 is deuterium; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or one or more adjacent pairs are combined with each other to form a substituted or unsubstituted ring,
    R6 내지 R8 중 적어도 하나의 인접한 어느 한 쌍 이상이 서로 결합하여 치환 또는 비치환된 방향족 탄화수소고리를 형성하고, 상기 R6 내지 R8 중 적어도 하나의 인접한 어느 한 쌍 이상이 서로 결합하여 치환 또는 비치환된 방향족 탄화수소고리를 형성하지 않는 나머지는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,At least one adjacent pair of at least one of R6 to R8 is bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring, and at least one adjacent pair of at least one of R6 to R8 is bonded to each other to form a substituted or unsubstituted aromatic hydrocarbon ring. The remainders that do not form an aromatic hydrocarbon ring are the same or different, and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    r1 내지 r7은 각각 1 내지 4의 정수이고,r1 to r7 are each integers from 1 to 4,
    r8은 1 내지 5의 정수이며,r8 is an integer from 1 to 5,
    상기 r6 내지 r8 중 적어도 하나는 2 이상이며,At least one of r6 to r8 is 2 or more,
    상기 r1이 2 이상인 경우, 상기 2 이상의 R1은 서로 같거나 상이하며,When r1 is 2 or more, the 2 or more R1 are the same or different from each other,
    상기 r2가 2 이상인 경우, 상기 2 이상의 R2는 서로 같거나 상이하고,When r2 is 2 or more, R2 of 2 or more is the same or different from each other,
    상기 r3가 2 이상인 경우, 상기 2 이상의 R3는 서로 같거나 상이하며,When r3 is 2 or more, the 2 or more R3s are the same or different from each other,
    상기 r4가 2 이상인 경우, 상기 2 이상의 R4는 서로 같거나 상이하고,When r4 is 2 or more, the 2 or more R4 are the same or different from each other,
    상기 r5가 2 이상인 경우, 상기 2 이상의 R5는 서로 같거나 상이하며,When r5 is 2 or more, the 2 or more R5 are the same or different from each other,
    상기 r6가 2 이상인 경우, 상기 2 이상의 R6는 서로 같거나 상이하고,When r6 is 2 or more, the 2 or more R6 are the same or different from each other,
    상기 r7가 2 이상인 경우, 상기 2 이상의 R7는 서로 같거나 상이하며,When r7 is 2 or more, the 2 or more R7 are the same or different from each other,
    상기 r8가 2 이상인 경우, 상기 2 이상의 R8는 서로 같거나 상이하다.When r8 is 2 or more, the 2 or more R8s are the same or different from each other.
  2. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 1-1인 것인 화합물:The compound according to claim 1, wherein the formula 1 is the following formula 1-1:
    [화학식 1-1][Formula 1-1]
    Figure PCTKR2023004877-appb-img-000089
    Figure PCTKR2023004877-appb-img-000089
    상기 화학식 1-1에 있어서,In Formula 1-1,
    R2, R4 내지 R8, r2, r4 내지 r8 및 Ar1의 정의는 상기 화학식 1에서 정의한 바와 동일하다.The definitions of R2, R4 to R8, r2, r4 to r8, and Ar1 are the same as those defined in Formula 1 above.
  3. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 1-2 내지 1-5 중 어느 하나인 것인 화합물:The compound according to claim 1, wherein Formula 1 is any one of the following Formulas 1-2 to 1-5:
    [화학식 1-2][Formula 1-2]
    Figure PCTKR2023004877-appb-img-000090
    Figure PCTKR2023004877-appb-img-000090
    [화학식 1-3][Formula 1-3]
    Figure PCTKR2023004877-appb-img-000091
    Figure PCTKR2023004877-appb-img-000091
    [화학식 1-4][Formula 1-4]
    Figure PCTKR2023004877-appb-img-000092
    Figure PCTKR2023004877-appb-img-000092
    [화학식 1-5][Formula 1-5]
    Figure PCTKR2023004877-appb-img-000093
    Figure PCTKR2023004877-appb-img-000093
    상기 화학식 1-2 내지 1-5에 있어서,In Formulas 1-2 to 1-5,
    R1, R3 내지 R8, r1, r3 내지 r8 및 Ar1의 정의는 상기 화학식 1에서 정의한 바와 동일하고,The definitions of R1, R3 to R8, r1, r3 to r8 and Ar1 are the same as those defined in Formula 1 above,
    R'2 및 R21은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 시아노기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알케닐기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며,R'2 and R21 are the same or different from each other and are each independently hydrogen; heavy hydrogen; halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    r'2는 1 내지 4의 정수이고,r'2 is an integer from 1 to 4,
    r21은 1 내지 6의 정수이며,r21 is an integer from 1 to 6,
    상기 r'2가 2 이상인 경우, 상기 2 이상의 R'2는 서로 같거나 상이하고,When r'2 is 2 or more, R'2 of 2 or more is the same as or different from each other,
    상기 r21이 2 이상인 경우, 상기 2 이상의 R21은 서로 같거나 상이하다.When r21 is 2 or more, the 2 or more R21s are the same or different from each other.
  4. 청구항 1에 있어서, 상기 R4는 탄소수 6 내지 30의 단환 또는 다환의 아릴기인 것인 화합물.The compound according to claim 1, wherein R4 is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  5. 청구항 1에 있어서, 상기 R5는 수소; 중수소; 또는 탄소수 6 내지 30의 단환 또는 다환의 아릴기이거나, 인접한 어느 한 쌍 이상은 서로 결합하여 탄소수 1 내지 30의 직쇄 또는 분지쇄의 알킬기로 치환 또는 비치환된 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성하는 것인 화합물.The method of claim 1, wherein R5 is hydrogen; heavy hydrogen; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms, wherein at least one adjacent pair is bonded to each other and substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms. A compound that forms a hydrocarbon ring.
  6. 청구항 1에 있어서, 상기 Ar1은 수소; 중수소; 또는 탄소수 6 내지 30의 단환의 아릴기인 것인 화합물.The method according to claim 1, wherein Ar1 is hydrogen; heavy hydrogen; Or a compound that is a monocyclic aryl group having 6 to 30 carbon atoms.
  7. 청구항 1 에 있어서, 상기 R6 내지 R8 중 적어도 하나의 인접한 어느 한 쌍 이상이 서로 결합하여 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성하고, 상기 R6 내지 R8 중 적어도 하나의 인접한 어느 한 쌍 이상이 서로 결합하여 탄소수 6 내지 30의 단환 또는 다환의 방향족 탄화수소고리를 형성하지 않는 나머지는 서로 같거나 상이하고, 각각 독립적으로 수소; 또는 중수소인 것인 화합물.The method according to claim 1, wherein at least one adjacent pair of R6 to R8 combines with each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms, and at least one adjacent pair of R6 to R8 The remainders that do not combine with each other to form a monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms are the same or different, and each independently represents hydrogen; Or a compound that is deuterium.
  8. 청구항 1에 있어서, 상기 화학식 1은 하기 화합물 중에서 선택되는 어느 하나인 것인 화합물:The method according to claim 1, wherein the formula 1 is any one selected from the following compounds:
    Figure PCTKR2023004877-appb-img-000094
    Figure PCTKR2023004877-appb-img-000094
    Figure PCTKR2023004877-appb-img-000095
    Figure PCTKR2023004877-appb-img-000095
    Figure PCTKR2023004877-appb-img-000096
    Figure PCTKR2023004877-appb-img-000096
    Figure PCTKR2023004877-appb-img-000097
    Figure PCTKR2023004877-appb-img-000097
    Figure PCTKR2023004877-appb-img-000098
    Figure PCTKR2023004877-appb-img-000098
    Figure PCTKR2023004877-appb-img-000099
    Figure PCTKR2023004877-appb-img-000099
    Figure PCTKR2023004877-appb-img-000100
    Figure PCTKR2023004877-appb-img-000100
    Figure PCTKR2023004877-appb-img-000101
    Figure PCTKR2023004877-appb-img-000101
    Figure PCTKR2023004877-appb-img-000102
    Figure PCTKR2023004877-appb-img-000102
    Figure PCTKR2023004877-appb-img-000103
    Figure PCTKR2023004877-appb-img-000103
    Figure PCTKR2023004877-appb-img-000104
    Figure PCTKR2023004877-appb-img-000104
    Figure PCTKR2023004877-appb-img-000105
    Figure PCTKR2023004877-appb-img-000105
    Figure PCTKR2023004877-appb-img-000106
    Figure PCTKR2023004877-appb-img-000106
    Figure PCTKR2023004877-appb-img-000107
    Figure PCTKR2023004877-appb-img-000107
    Figure PCTKR2023004877-appb-img-000108
    Figure PCTKR2023004877-appb-img-000108
    Figure PCTKR2023004877-appb-img-000109
    Figure PCTKR2023004877-appb-img-000109
    Figure PCTKR2023004877-appb-img-000110
    Figure PCTKR2023004877-appb-img-000110
    Figure PCTKR2023004877-appb-img-000111
    Figure PCTKR2023004877-appb-img-000111
    Figure PCTKR2023004877-appb-img-000112
    Figure PCTKR2023004877-appb-img-000112
    Figure PCTKR2023004877-appb-img-000113
    Figure PCTKR2023004877-appb-img-000113
  9. 제1 전극; 제2 전극; 및 상기 제1 전극과 제2 전극 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1 층 이상은 청구항 1 내지 8 중 어느 한 항의 화합물을 포함하는 것인 유기 발광 소자.first electrode; second electrode; and an organic light emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound of any one of claims 1 to 8.
  10. 청구항 9에 있어서, 상기 유기물층은 정공주입층, 정공수송층, 또는 정공 주입 및 수송층을 포함하고, 상기 정공주입층, 정공수송층, 또는 정공 주입 및 수송층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic light emitting device of claim 9, wherein the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the compound.
  11. 청구항 9에 있어서, 상기 유기물층은 전자차단층을 포함하고, 상기 전자차단층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic light emitting device of claim 9, wherein the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound.
PCT/KR2023/004877 2022-07-14 2023-04-11 Compound and organic light-emitting device comprising same WO2024014660A1 (en)

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Citations (5)

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Publication number Priority date Publication date Assignee Title
KR20080017562A (en) * 2006-08-21 2008-02-27 (주)그라쎌 Luminescent compounds and electroluminescent device using the same
CN108658953A (en) * 2018-05-16 2018-10-16 上海道亦化工科技有限公司 A kind of compound based on dibenzofurans and carbazole and application thereof and luminescent device
CN111978329A (en) * 2020-09-09 2020-11-24 烟台显华化工科技有限公司 Compound, hole transport material, organic electroluminescent device and display device
WO2021172664A1 (en) * 2020-02-28 2021-09-02 주식회사 엘지화학 Organic light-emitting device
CN113563253A (en) * 2020-04-28 2021-10-29 江苏三月科技股份有限公司 Organic compound with triarylamine as core and application thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100430549B1 (en) 1999-01-27 2004-05-10 주식회사 엘지화학 New organomattalic complex molecule for the fabrication of organic light emitting diodes

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20080017562A (en) * 2006-08-21 2008-02-27 (주)그라쎌 Luminescent compounds and electroluminescent device using the same
CN108658953A (en) * 2018-05-16 2018-10-16 上海道亦化工科技有限公司 A kind of compound based on dibenzofurans and carbazole and application thereof and luminescent device
WO2021172664A1 (en) * 2020-02-28 2021-09-02 주식회사 엘지화학 Organic light-emitting device
CN113563253A (en) * 2020-04-28 2021-10-29 江苏三月科技股份有限公司 Organic compound with triarylamine as core and application thereof
CN111978329A (en) * 2020-09-09 2020-11-24 烟台显华化工科技有限公司 Compound, hole transport material, organic electroluminescent device and display device

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