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WO2024122840A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2024122840A1
WO2024122840A1 PCT/KR2023/015484 KR2023015484W WO2024122840A1 WO 2024122840 A1 WO2024122840 A1 WO 2024122840A1 KR 2023015484 W KR2023015484 W KR 2023015484W WO 2024122840 A1 WO2024122840 A1 WO 2024122840A1
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carbon atoms
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윤정민
박종진
이재탁
한수진
허동욱
홍성길
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LG Chem Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection 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
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    • 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
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    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • 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
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    • 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.
  • 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 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.
  • A1 is the formula A below,
  • L1 is direct bonding; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted hetero arylene group,
  • L2 is an arylene group
  • l1 and l2 are each integers from 1 to 3,
  • L2 of 2 or more is the same or different from each other
  • At least one of Y1 to Y5 is N, and the remainder other than N among Y1 to Y5 are the same or different from each other and are each independently CG1,
  • G1 is hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or one or more pairs of adjacent groups are combined with each other to form a substituted or unsubstituted ring,
  • R1 to R6 are the same as or different from each other, and are each independently hydrogen; or deuterium,
  • G2 to G6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or one or more pairs of adjacent groups among G3 to G6 are combined with each other to form a substituted or unsubstituted ring with G7,
  • G7 is hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • G2 to G7 is a site bound to L1 of Formula 1,
  • X1 is O or S.
  • an exemplary embodiment of 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 includes the above-described 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 can improve efficiency, low driving voltage, and/or lifespan characteristics in an organic light-emitting device.
  • the compounds described herein can be used as electron injection, electron transport, electron injection and electron transport, or hole blocking materials.
  • it has low high efficiency and long lifespan.
  • 1 and 2 show examples of organic light-emitting devices according to an exemplary embodiment of the present specification.
  • the above formula (1) is that a 6-membered heterocycle containing at least 1 N at positions 1 and 2 of naphthalene is bonded through L1, and a benzimidazole derivative or benzothiazole derivative is bonded to L2.
  • a compound bonded through a naphthalene core it exhibits high heat resistance, and 6-membered heterocycles containing 1 or more N, benzimidazole derivatives, and benzothiazole derivatives have an electron depletion structure to increase the polarity (dipole moment) of the molecule. Therefore, Formula 1 can be included in the organic material layer of the organic light emitting device to improve efficiency, lower driving voltage, and improve lifespan characteristics.
  • the conjugation length of the molecular structure is shortened compared to other naphthalene substituent positions, and the three-dimensional structure is large, which improves electron mobility when applied to organic light-emitting devices. It can increase efficiency and extend lifespan.
  • sublimation purification of the material does not have a flat structure, there is an advantage that sublimation purification is possible at low temperatures.
  • 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 heteroaryl groups, is substituted with a substituent where 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 .
  • the connection of three substituents not only means that (substituent 1) - (substituent 2) - (substituent 3) are connected in succession, but also that (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.
  • halogen groups include fluoro group, chloro group, bromo group, or iodo group.
  • 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-dimethylcyclophene.
  • 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. .
  • a haloalkyl group means that at least one halogen group is substituted for the hydrogen of 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 , , , , , , , and 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 at 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 , where 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 -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, 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.
  • 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.
  • N-arylheteroarylamine group refers to an amine group in which the N of the amine group is substituted with an aryl group and a heteroaryl 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.
  • 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, and 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.
  • an arylene group refers to an aryl group having two bonding positions, that is, a bivalent group.
  • the description of the aryl group described above can be applied, except that each of these is a divalent group.
  • a heteroarylene group refers to a heteroaryl group having two bonding positions, that is, a bivalent group.
  • the description of the heteroaryl group described above can be applied, except that each of these is a divalent group.
  • adjacent groups combine with each other to form a ring means a substituted or unsubstituted hydrocarbon ring by combining with adjacent groups; Or it means forming a substituted or unsubstituted heterocycle.
  • ring refers to a substituted or unsubstituted hydrocarbon ring; Or it means a substituted or unsubstituted heterocycle.
  • the hydrocarbon ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a condensed ring of an aromatic hydrocarbon and an aliphatic hydrocarbon, and may be selected from examples of the cycloalkyl group or aryl group, excluding those that are not monovalent.
  • a heterocycle includes one or more atoms other than carbon and a heteroatom.
  • the heteroatom 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 the heteroaryl group except that it is not monovalent.
  • an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms.
  • aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, and azocaine. , thiocane, etc., but is not limited thereto.
  • Formula 1 is the following Formula 1-1 or Formula 1-2.
  • R1 to R6, L1, L2, l1, l2, A1, and Y1 to Y5 are the same as those defined in Formula 1 above.
  • R1 to R6 are hydrogen.
  • R1 to R6 are deuterium.
  • G2 to G6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Or, it is a substituted or unsubstituted aryl group, or one or more pairs of adjacent groups among G3 to G6 are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring with G7.
  • G2 to G6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or one or more pairs of adjacent groups among G3 to G6 are combined with each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms substituted or unsubstituted by G7. do.
  • G2 to G6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or one or more pairs of adjacent groups among G3 to G6 are combined with each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms substituted or unsubstituted by G7. do.
  • G2 to G6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Alkyl group; Or, it is an aryl group, or one or more pairs of adjacent groups among G3 to G6 are combined with each other to form an aromatic hydrocarbon ring substituted or unsubstituted by G7.
  • G2 to G6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; Or, it is a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or one or more pairs of adjacent groups among G3 to G6 are combined with each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms unsubstituted or substituted by G7.
  • G2 to G6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 20 carbon atoms; Or, it is a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or one or more pairs of adjacent groups among G3 to G6 are combined with each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms unsubstituted or substituted by G7.
  • G2 to G6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; ethyl group; phenyl group; Or, it is a naphthyl group, or one or more pairs of adjacent groups among G3 to G6 are combined with each other to form benzene substituted or unsubstituted by G7.
  • one or more pairs of adjacent groups among G3 to G6 are combined with each other to form a ring substituted or unsubstituted by G7.
  • one or more pairs of adjacent groups among G3 to G6 are combined with each other to form an aromatic hydrocarbon ring substituted or unsubstituted by G7.
  • one or more pairs of adjacent groups among G3 to G6 are combined with each other to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms unsubstituted or substituted with G7.
  • one or more pairs of adjacent groups among G3 to G6 are combined with each other to form an aromatic hydrocarbon ring having 6 to 20 carbon atoms unsubstituted or substituted with G7.
  • one or more pairs of adjacent groups among G3 to G6 are combined with each other to form benzene substituted or unsubstituted by G7.
  • one or more pairs of adjacent groups among G3 to G6 combine with each other to form benzene.
  • any one of G2 to G6 is a site bound to L1 of Formula 1 above.
  • any one of G2 to G7 is a site bound to L1 of Formula 1 above.
  • Formula A is any one of the following structures.
  • G2 to G6 and G71 to G78 is a site bonded to L1 of Formula 1, and the remainder of G2 to G6 and G71 to G78 that is not bonded to Formula 1 is the same or different and each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • X1 is O or S.
  • X1 is O.
  • X1 is S.
  • Formula A is any one of the following structures.
  • G2 to G6 and G71 to G78 is a site bonded to L1 of Formula 1, and the remaining portions of G2 to G6 and G71 to G78 that are not bonded to Formula 1 are the same or different and each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • G2 to G6 are the same as 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.
  • G2 to G6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; 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; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • G2 to G6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms.
  • G2 to G6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Alkyl group; Aryl group unsubstituted or substituted with deuterium, cyano group, alkyl group, aryl group, or heteroaryl group; Or it is a heteroaryl group substituted or unsubstituted by an alkyl group or an aryl group.
  • G2 to G6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; 6 to 6 carbon atoms substituted or unsubstituted with deuterium, cyano group, straight or branched chain alkyl group with 1 to 30 carbon atoms, monocyclic or polycyclic aryl group with 6 to 30 carbon atoms, or monocyclic or polycyclic heteroaryl group with 2 to 30 carbon atoms 30 monocyclic or polycyclic aryl groups; or a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • G2 to G6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 20 carbon atoms; Substituted or unsubstituted with deuterium, cyano group, straight or branched chain alkyl group having 1 to 20 carbon atoms, monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms, or unsubstituted 20 monocyclic or polycyclic aryl groups; or a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.
  • G2 to G6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; ethyl group; isopropyl group; tert-butyl group; A phenyl group substituted or unsubstituted by deuterium, a cyano group, a straight-chain or branched alkyl group having 1 to 30 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms; A biphenyl group unsubstituted or substituted with deuterium, a cyano group, or a straight or branched alkyl group having 1 to 30 carbon atoms; naphthyl group; A pyridine group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or
  • G2 to G6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; ethyl group; isopropyl group; tert-butyl group; A phenyl group substituted or unsubstituted by deuterium, a cyano group, a straight-chain or branched alkyl group having 1 to 20 carbon atoms, a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms, or a monocyclic or polycyclic heteroaryl group having 2 to 20 carbon atoms; A biphenyl group unsubstituted or substituted with deuterium, a cyano group, or a straight or branched alkyl group having 1 to 20 carbon atoms; naphthyl group; A pyridine group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or
  • G2 to G6 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; ethyl group; isopropyl group; tert-butyl group; A phenyl group unsubstituted or substituted with deuterium, cyano group, methyl group, isopropyl group, tert-butyl group, naphthyl group, or pyridine group; Biphenyl group substituted or unsubstituted with deuterium, cyano group, or isopropyl group; naphthyl group; A pyridine group substituted or unsubstituted with a methyl group or a phenyl group; Pyrimidine group; Pyridazine group; Quinoline group; Isoquinoline group; Dibenzofuran group; Or it is a dibenzothiophene group.
  • G7 is hydrogen; Or it is deuterium.
  • G7 is hydrogen
  • G7 is deuterium
  • G71 to G78 are the same as or different from each other and are each independently hydrogen; Or it is deuterium.
  • any one of G2 to G7 is a site bound to L1 of Formula 1 above.
  • any one of G2 to G6 is a site bound to L1 of Formula 1 above.
  • G71 to G78 are hydrogen.
  • G71 to G78 are deuterium.
  • At least one of Y1 to Y5 is N, and the remainders other than N among Y1 to Y5 are the same or different from each other, and are each independently CG1.
  • any one of Y1 to Y5 is N, and the remainders other than N among Y1 to Y5 are the same or different from each other, and are each independently CG1.
  • any two of Y1 to Y5 are N, and the remaining ones that are not N among Y1 to Y5 are the same or different from each other and are each independently CG1.
  • any three of Y1 to Y5 are N, and the remaining ones that are not N among Y1 to Y5 are the same or different from each other and are each independently CG1.
  • any four of Y1 to Y5 are N, and the remainder that is not N among Y1 to Y5 is CG1.
  • Y1 to Y5 are N.
  • Y1 is N
  • Y2 to Y5 are the same as or different from each other, and each independently represents CG1.
  • Y2 is N
  • Y1 and Y3 to Y5 are the same as or different from each other, and each independently represents CG1.
  • Y3 is N
  • Y1, Y2, Y4, and Y5 are the same as or different from each other, and each independently represents CG1.
  • Y1 and Y2 are N, and Y3 to Y5 are the same as or different from each other and are each independently CG1.
  • Y1 and Y3 are N, and Y2, Y4, and Y5 are the same as or different from each other, and each independently represents CG1.
  • Y1 and Y4 are N, and Y2, Y3, and Y5 are the same as or different from each other, and each independently represents CG1.
  • Y1 and Y5 are N, and Y2 to Y4 are the same as or different from each other and are each independently CG1.
  • Y2 and Y3 are N, and Y1, Y4, and Y5 are the same as or different from each other, and each independently represents CG1.
  • Y2 and Y4 are N, and Y1, Y3, and Y5 are the same as or different from each other, and each independently represents CG1.
  • Y1, Y2 and Y3 are N, and Y4 and Y5 are the same as or different from each other and are each independently CG1.
  • Y1, Y2 and Y4 are N
  • Y3 and Y5 are the same or different from each other and are each independently CG1.
  • Y1, Y2 and Y5 are N, and Y3 and Y4 are the same as or different from each other and are each independently CG1.
  • Y1, Y3 and Y4 are N
  • Y2 and Y5 are the same as or different from each other and are each independently CG1.
  • Y1, Y3 and Y5 are N, and Y2 and Y4 are the same as or different from each other and are each independently CG1.
  • Y2 to Y4 are N
  • Y1 and Y5 are the same as or different from each other, and each independently represents CG1.
  • Y1 and Y3 to Y5 are N, and Y2 is CG1.
  • Y1, Y2, Y4, and Y5 are N, and Y3 is CG1.
  • Y1 to Y4 are N, and Y5 is CG1.
  • the above is any one selected from the structures below.
  • L2 and l2 are the same as defined in Formula 1 above,
  • G11 to G15 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or, it is a substituted or unsubstituted heteroaryl group, or one or more pairs of adjacent groups are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.
  • G1 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted carbon number cycloalkyl group; Substituted or unsubstituted aryl group; Or, it is a substituted or unsubstituted heteroaryl group, or one or more pairs of adjacent groups are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.
  • G1 is hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; 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, or one or more pairs of adjacent groups are combined with each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • G1 is hydrogen; heavy hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or, it is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 3 to 20 carbon atoms, or one or more pairs of adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • G1 is hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; A monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or one or more pairs of adjacent groups are bonded to each other to form a monocyclic or polycyclic heteroaryl group having 6 to 30 carbon atoms.
  • G1 is hydrogen; heavy hydrogen; A straight or branched alkyl group having 1 to 20 carbon atoms; A monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 3 to 20 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or one or more pairs of adjacent groups are bonded to each other to form a monocyclic or polycyclic heteroaryl group having 6 to 20 carbon atoms.
  • G1 is hydrogen; heavy hydrogen; methyl group; Cyclohexyl group; A straight or branched alkyl group having 1 to 30 carbon atoms; a phenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; Biphenyl group; naphthyl group; Or, it is a pyridine group substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, or any pair of adjacent groups combine with each other to form benzene.
  • G1 is hydrogen; heavy hydrogen; methyl group; Cyclohexyl group; A straight or branched alkyl group having 1 to 20 carbon atoms; a phenyl group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; Biphenyl group; naphthyl group; Or, it is a pyridine group substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms, or one or more pairs of adjacent groups combine with each other to form benzene.
  • G1 is hydrogen; heavy hydrogen; methyl group; Cyclohexyl group; A phenyl group unsubstituted or substituted with a methyl group, tert-butyl group, or cyclohexyl group; Biphenyl group; naphthyl group; Or, it is a pyridine group substituted or unsubstituted with a methyl group, or one or more pairs of adjacent groups combine with each other to form benzene.
  • G1 is hydrogen; heavy hydrogen; Or, it is a phenyl group, or one or more pairs of adjacent groups combine with each other to form benzene.
  • G11 to G15 are the same as or different from each other, and are each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted carbon number cycloalkyl group; Substituted or unsubstituted aryl group; Or, it is a substituted or unsubstituted heteroaryl group, or one or more pairs of adjacent groups are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.
  • G11 to G15 are the same as or different from each other, and are each independently hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; 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, or one or more pairs of adjacent groups are combined with each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • G11 to G15 are the same as or different from each other, and are each independently hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or, it is a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 3 to 20 carbon atoms, or one or more pairs of adjacent groups are bonded to each other to form a substituted or unsubstituted monocyclic or polycyclic aromatic hydrocarbon ring having 6 to 20 carbon atoms.
  • G11 to G15 are the same as or different from each other, and are each independently hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; A monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or one or more pairs of adjacent groups are bonded to each other to form a monocyclic or polycyclic heteroaryl group having 6 to 30 carbon atoms.
  • G11 to G15 are the same as or different from each other, and are each independently hydrogen; A straight or branched alkyl group having 1 to 20 carbon atoms; A monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms substituted or unsubstituted with a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; or a monocyclic or polycyclic heteroaryl group having 3 to 20 carbon atoms substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or one or more pairs of adjacent groups are bonded to each other to form a monocyclic or polycyclic heteroaryl group having 6 to 20 carbon atoms.
  • G11 to G15 are the same as or different from each other, and are each independently hydrogen; methyl group; Cyclohexyl group; A straight or branched alkyl group having 1 to 30 carbon atoms; a phenyl group unsubstituted or substituted with a straight-chain or branched alkyl group having 1 to 30 carbon atoms, or a monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; Biphenyl group; naphthyl group; Or, it is a pyridine group substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms, or one or more pairs of adjacent groups combine with each other to form benzene.
  • G11 to G15 are the same as or different from each other, and are each independently hydrogen; methyl group; Cyclohexyl group; A straight or branched alkyl group having 1 to 20 carbon atoms; a phenyl group substituted or unsubstituted with a straight-chain or branched alkyl group having 1 to 20 carbon atoms, or a monocyclic or polycyclic cycloalkyl group having 3 to 20 carbon atoms; Biphenyl group; naphthyl group; Or, it is a pyridine group substituted or unsubstituted with a straight-chain or branched-chain alkyl group having 1 to 20 carbon atoms, or one or more pairs of adjacent groups combine with each other to form benzene.
  • G11 to G15 are the same as or different from each other, and are each independently hydrogen; methyl group; Cyclohexyl group; A phenyl group unsubstituted or substituted with a methyl group, tert-butyl group, or cyclohexyl group; Biphenyl group; naphthyl group; Or, it is a pyridine group substituted or unsubstituted with a methyl group, or one or more pairs of adjacent groups combine with each other to form benzene.
  • G11 to G15 are hydrogen; heavy hydrogen; Or, it is a phenyl group, or one or more pairs of adjacent groups combine with each other to form benzene.
  • l1 is 1.
  • l1 is 2.
  • l1 is 3.
  • l2 is 1.
  • l2 is 2.
  • l1 when l1 is 2 or more, it means that two or more L1 are the same or different from each other, and each L1 is connected in series.
  • L1 when l1 is 3 and L1 is a phenylene group, a naphthylene group, and a phenylene group, they may be connected as follows, but are not limited to this, and the order or connection position of each L1 may be different.
  • A1 means bonded to the third terminal substituent in the exemplified structure, that is, the phenylene group, and * means bonded to Formula 1.
  • L1 is a direct bond; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms, and L2 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L1 is a direct bond; Or it is a substituted or unsubstituted arylene group.
  • L1 is a direct bond; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
  • L1 is a direct bond; A substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
  • L1 is a direct bond; Arylene group; Or it is a heteroarylene group.
  • L1 is a direct bond; A monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; Or it is a monocyclic or polycyclic heteroarylene group having 2 to 30 carbon atoms.
  • L1 is a direct bond; A monocyclic or polycyclic arylene group having 6 to 20 carbon atoms; Or it is a monocyclic or polycyclic heteroarylene group having 2 to 20 carbon atoms.
  • L1 is a direct bond; phenylene group; Biphenylylene group; naphthylene group; A divalent pyridine group; Or it is a divalent dibenzofuran group.
  • L2 is a substituted or unsubstituted arylene group.
  • L2 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L2 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.
  • L2 is an arylene group.
  • L2 is a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.
  • L2 is a monocyclic or polycyclic arylene group having 6 to 20 carbon atoms.
  • L2 is a phenylene group.
  • 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.
  • 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 an electron injection layer, an electron transport layer, or an electron injection and transport layer, and the electron injection layer, an electron transport layer, or an electron injection and transport layer includes the compound.
  • the organic material layer is one or more layers among a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer. It further includes.
  • 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.
  • 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 second electrode is a cathode or anode.
  • 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.
  • the compound of Formula 1 may be formed into 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 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 : Combination of metal and oxide such as Sb; 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 host includes, but is not limited to, a compound represented by the following formula H-1.
  • 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.
  • 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.
  • T1 to T5 are the same or different from each other, and are each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Or a substituted or unsubstituted aryl group,
  • t1 and t2 are each integers from 1 to 5
  • t3 is an integer from 1 to 3
  • t4 and t5 are each integers from 1 to 4,
  • t1 is 2 or more, the 2 or more T1 are the same or different from each other,
  • T2 of 2 or more is the same or different from each other
  • t3 is 2 or more, the 2 or more T3 are the same or different from each other,
  • t4 is 2 or more, the 2 or more T4 are the same or different from each other,
  • t5 When t5 is 2 or more, the 2 or more T5s are the same or different from each other.
  • T1 to T5 are the same or different from each other, and are each independently hydrogen; A substituted or unsubstituted straight-chain or branched alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; Or it is a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • T1 to T5 are the same or different from each other, and are each independently hydrogen; A straight or branched alkyl group having 1 to 30 carbon atoms; A monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; Or it is a monocyclic or polycyclic aryl group 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.
  • T1 to T5 are the same or different from each other, and are each independently hydrogen; methyl group; tert-butyl group; Diphenylamine group; Or it is a phenyl group substituted or unsubstituted with a methyl group, or a tert-butyl group.
  • Formula D-1 is represented by the following compound.
  • 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 with respect 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 represented by the following formula HI-1.
  • R301 to R306 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 a substituted or unsubstituted heterocyclic group,
  • L301 and L302 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted arylene group; Or it is a substituted or unsubstituted divalent heterocyclic group.
  • R301 and R302 are the same or different from each other, and are each independently a straight-chain or branched alkyl group having 1 to 30 carbon atoms.
  • R301 and R302 are methyl groups.
  • L301 and L302 are a direct bond.
  • R303 to R306 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.
  • R303 to R306 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; Or it is a monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms that is substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.
  • R303 to R306 are the same as or different from each other, and are each independently a phenyl group; Or it is a carbazole group substituted or unsubstituted with a phenyl group.
  • the formula HI-1 is represented by the following compound.
  • 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 preferably a material that can receive holes from the anode or hole injection layer and transfer them to the light emitting layer, and has high mobility for holes. 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.
  • 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 HT-1 is represented by the following compound.
  • the hole transport layer includes a compound represented by the following chemical formula HT-2, but is not limited thereto.
  • R315 to R317 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; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof, or by combining with adjacent groups to form a substituted or unsubstituted ring,
  • r315 is an integer from 1 to 5, and when r315 is 2 or more, 2 or more R315 are the same or different from each other,
  • r316 is an integer of 1 to 5, and when r316 is 2 or more, 2 or more R316 are the same or different from each other.
  • R317 is a substituted or unsubstituted aryl group; Substituted or unsubstituted heteroaryl group; and any one selected from the group consisting of combinations thereof.
  • R317 is a carbazole group; phenyl group; Biphenyl group; and any one selected from the group consisting of combinations thereof.
  • R315 and R316 are the same or different from each other and are each independently a substituted or unsubstituted aryl group, or are combined with adjacent groups to form an aromatic hydrocarbon ring substituted with an alkyl group.
  • R315 and R316 are the same or different from each other, and are each independently a phenyl group, or are combined with adjacent groups to form an indene substituted with a methyl group.
  • the chemical formula HT-2 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 well inject electrons from the cathode and transfer them to the light-emitting layer.
  • a material with high mobility for electrons is preferable.
  • 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.
  • suitable cathode materials are conventional materials with a low work function followed by an aluminum or silver layer.
  • cesium, barium, calcium, ytterbium, and samarium 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.
  • the organic light emitting device includes an additional electron injection layer other than the electron injection layer containing Formula 1
  • the electron injection material has excellent electron transport ability
  • the second electrode It is desirable to have an excellent electron receiving effect from and an excellent electron injection effect with respect to the light emitting layer or light emitting material.
  • 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.
  • 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) (o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc. , but is not limited to this.
  • the electron injection and transport layer is a layer that transports electrons to the light-emitting layer. If the electron injection and transport layer includes an additional electron injection and transport layer in addition to the electron injection and transport layer containing Formula 1, the materials exemplified for the electron transport layer and electron injection layer may be used, but are not limited thereto.
  • the electron injection and transport layer may further include a metal complex compound.
  • the metal complex compound is as described above.
  • 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.
  • Known materials can be used without limitation, and the materials exemplified in the description of the hole injection layer can 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.
  • 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.
  • Compound 2 was prepared in the same manner as in Preparation Example 1, except that each starting material was used according to the above reaction formula.
  • Compound 3 was prepared in the same manner as in Preparation Example 1, except that each starting material was used according to the above reaction formula.
  • Compound 4 was prepared in the same manner as in Preparation Example 1, except that each starting material was used according to the above reaction scheme.
  • Compound 5 was prepared in the same manner as in Preparation Example 1, except that each starting material was used according to the above reaction scheme.
  • Compound 6 was prepared in the same manner as in Preparation Example 1, except that each starting material was used according to the above reaction scheme.
  • Compound 7 was prepared in the same manner as in Preparation Example 1, except that each starting material was used according to the above reaction scheme.
  • Compound 8 was prepared in the same manner as in Preparation Example 1, except that each starting material was used according to the above reaction scheme.
  • Compound 9 was prepared in the same manner as in Preparation Example 1, except that each starting material was used according to the above reaction scheme.
  • Compound 10 was prepared in the same manner as in Preparation Example 1, except that each starting material was prepared according to the above reaction scheme.
  • Compound 11 was prepared in the same manner as in Preparation Example 1, except that each starting material was prepared according to the above reaction scheme.
  • Compound 12 was prepared in the same manner as in Preparation Example 1, except that each starting material was used according to the above reaction scheme.
  • Compound 13 was prepared in the same manner as in Preparation Example 1, except that each starting material was used according to the above reaction scheme.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) to a thickness of 1000 ⁇ was placed in distilled water with a detergent dissolved in it and washed with ultrasonic waves.
  • a detergent from Fischer Co. was used, and distilled water that was filtered secondarily using a filter from Millipore Co. was used.
  • ultrasonic cleaning was repeated twice with distilled water for 10 minutes.
  • the following compound HI-A was thermally vacuum deposited to a thickness of 600 ⁇ to form a hole injection layer.
  • 50 ⁇ of the following compound HAT and 60 ⁇ of the following compound HT-A were sequentially vacuum deposited to form a first hole transport layer and a second hole transport layer.
  • the following compound BH and compound BD were vacuum deposited on the second hole transport layer to a film thickness of 200 ⁇ at a weight ratio of 25:1 to form a light emitting layer.
  • Compound 1 prepared previously and the following compound LiQ were vacuum deposited on the emitting layer at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 350 ⁇ .
  • a cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 ⁇ and aluminum to a thickness of 1000 ⁇ on the electron injection and transport layer.
  • LiF lithium fluoride
  • the deposition rate of organic materials was maintained at 0.4 ⁇ /sec to 0.9 ⁇ /sec
  • the deposition rate of lithium fluoride of the cathode was maintained at 0.3 ⁇ /sec
  • aluminum was maintained at 2 ⁇ /sec
  • the vacuum level during deposition was
  • An organic light emitting device was manufactured by maintaining 1 ⁇ 10 -7 torr to 5 ⁇ 10 -5 torr.
  • An organic light emitting device was manufactured in the same manner as in Example 1-1, except that compounds 2 to 13 shown in Table 1 below were used instead of compound 1 in Example 1-1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that compounds ET-1 to ET-9 in Table 1 below were used instead of compound 1 in Example 1-1.
  • the structures of compounds ET-1 to ET-9 in Table 1 below are as follows.
  • Example 1-1 One 4.19 6.85 (0.140, 0.092) 180 Example 1-2 2 4.15 6.94 (0.140, 0.092) 180 Example 1-3 3 4.23 6.74 (0.140, 0.092) 170 Example 1-4 4 4.19 6.89 (0.141, 0.092) 210 Examples 1-5 5 4.31 6.52 (0.140, 0.093) 220 Example 1-6 6 4.25 6.61 (0.140, 0.093) 210 Example 1-7 7 4.11 6.99 (0.140, 0.093) 205 Examples 1-8 8 4.23 6.79 (0.140, 0.092) 180 Example 1-9 9 4.34 6.57 (0.140, 0.092) 170 Examples 1-10 10 4.38 6.53 (0.140, 0.092) 180 Example 1-11 11 4.31 6.63 (0.141
  • the compound represented by Formula 1 according to the present specification can be used in the electron injection and transport layer of an organic light-emitting device.
  • Chemical formula 1 according to an exemplary embodiment of the present specification has a 6-membered heterocycle containing at least 1 N at positions 1 and 2 of naphthalene bonded through L1, and a benzimidazole derivative or benzothiazole derivative bonded through L2.
  • the naphthalene core exhibits high heat resistance
  • the 6-membered heterocycle containing 1 or more N, benzimidazole derivatives, and benzothiazole derivatives have an electron depletion structure, which can increase the polarity (dipole moment) of the molecule. Therefore, Formula 1 can be included in the organic material layer of the organic light-emitting device to improve efficiency, lower driving voltage, and improve lifespan characteristics.
  • Comparative Examples 1-1 and 1-2 apply a compound in which L2 is a direct bond to an organic light emitting device, and the conjugation length is excessively short, resulting in a significant decrease in driving voltage, efficiency, and lifespan compared to the examples of the present application.
  • the conjugation length of the molecular structure is shortened compared to other naphthalene substituent positions, and the three-dimensional structure is made large, so that it can be applied to organic light-emitting devices to improve electron mobility. It can increase efficiency and extend lifespan.
  • compounds with substituents bonded to positions 1, 4, 1, 5, 2, 6, or 2, 7 of naphthalene have significantly higher efficiency and lifespan than Examples 1-1 to 1-13 of the present specification. It can be seen that it is deteriorating significantly.

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  • Materials Engineering (AREA)
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  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé de formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2023/015484 2022-12-08 2023-10-10 Composé et dispositif électroluminescent organique le comprenant Ceased WO2024122840A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150117173A (ko) * 2014-04-09 2015-10-19 제일모직주식회사 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치
WO2016197353A1 (fr) * 2015-06-11 2016-12-15 Dow Global Technologies Llc Composé organique électroluminescent et dispositif organique électroluminescent le comprenant
KR20170049440A (ko) * 2015-10-27 2017-05-10 주식회사 엘지화학 유기 발광 소자
KR20200005489A (ko) * 2018-07-05 2020-01-15 주식회사 엘지화학 다환 화합물 및 이를 포함하는 유기 발광 소자
KR20220065123A (ko) * 2020-11-12 2022-05-20 주식회사 랩토 트리아진 또는 피리미딘 유도체, 및 이를 포함한 유기전계발광소자

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100430549B1 (ko) 1999-01-27 2004-05-10 주식회사 엘지화학 신규한 착물 및 그의 제조 방법과 이를 이용한 유기 발광 소자 및 그의 제조 방법

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150117173A (ko) * 2014-04-09 2015-10-19 제일모직주식회사 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치
WO2016197353A1 (fr) * 2015-06-11 2016-12-15 Dow Global Technologies Llc Composé organique électroluminescent et dispositif organique électroluminescent le comprenant
KR20170049440A (ko) * 2015-10-27 2017-05-10 주식회사 엘지화학 유기 발광 소자
KR20200005489A (ko) * 2018-07-05 2020-01-15 주식회사 엘지화학 다환 화합물 및 이를 포함하는 유기 발광 소자
KR20220065123A (ko) * 2020-11-12 2022-05-20 주식회사 랩토 트리아진 또는 피리미딘 유도체, 및 이를 포함한 유기전계발광소자

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