WO2023172112A1 - Composé et élément électroluminescent organique le comprenant - Google Patents

Composé et élément électroluminescent organique le comprenant Download PDF

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WO2023172112A1
WO2023172112A1 PCT/KR2023/003332 KR2023003332W WO2023172112A1 WO 2023172112 A1 WO2023172112 A1 WO 2023172112A1 KR 2023003332 W KR2023003332 W KR 2023003332W WO 2023172112 A1 WO2023172112 A1 WO 2023172112A1
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허동욱
윤정민
윤준
윤희경
이재탁
한수진
홍성길
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주식회사 엘지화학
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Priority to CN202380012748.0A priority Critical patent/CN117616024A/zh
Publication of WO2023172112A1 publication Critical patent/WO2023172112A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/08—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
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    • C07—ORGANIC CHEMISTRY
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    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/08—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic 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
    • 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
    • H10K50/165—Electron transporting layers comprising dopants
    • 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]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection 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
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom

Definitions

  • 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 composed 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 is When it falls back to the ground state, it glows.
  • This specification provides compounds and organic light-emitting devices containing the same.
  • An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
  • L1 and L2 are the same or different from each other and are each independently a substituted or unsubstituted arylene group
  • Ar1 and Ar2 are the same as or different from each other, and are each independently represented by the following formula A,
  • the portion of the benzene ring that does not have a substituent is substituted with hydrogen or deuterium.
  • X1 is N or CR1
  • X2 is N or CR2
  • X3 is N or CR3
  • X4 is N or CR4
  • X5 is N or CR5
  • At least two of X1 to X5 are N,
  • R1 to R5 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring,
  • an exemplary embodiment of the present specification includes an anode; cathode; and an organic light emitting device comprising at least one organic material layer provided between the anode and the cathode, wherein at least one layer of the organic material layer includes the compound represented by Formula 1.
  • 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.
  • it compared to existing organic light emitting devices, it has the effects of low driving voltage, high efficiency, and/or long lifespan.
  • Figure 1 shows an example of an organic light-emitting device in which a substrate 1, an anode 2, an organic material layer 10, and a cathode 9 are sequentially stacked.
  • Figure 2 shows the substrate (1), anode (2), hole injection layer (3), hole transport layer (4), light emitting layer (5), electron transport layer (6), electron injection layer (7), and cathode (9) sequentially.
  • An example of a stacked organic light emitting device is shown.
  • FIG. 3 shows a substrate (1), anode (2), hole injection layer (3), first hole transport layer (4-1), second hole transport layer (4-2), light emitting layer (5), and electron transport and injection layer.
  • (8) and the cathode (9) are sequentially stacked to show an example of an organic light emitting device.
  • Figure 4 shows an organic structure in which a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), light emitting layer (5), electron transport and injection layer (8), and cathode (9) are sequentially stacked.
  • a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), light emitting layer (5), electron transport and injection layer (8), and cathode (9) are sequentially stacked.
  • An example of a light emitting device is shown.
  • 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 (-CN); nitro group; hydroxyl group; Alkyl group; Cycloalkyl group; Alkoxy group; Phosphine oxide group; Aryloxy group; Alkylthioxy group; Arylthioxy group; Alkyl sulphoxy group; Aryl sulfoxy group; alkenyl group; silyl group; boron group; Amine group; Aryl group; Alternatively, it means that it is substituted with one or two or more substituents selected from the group consisting of heterocyclic groups, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituents.
  • a substituent group in which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.
  • substituted or unsubstituted refers to deuterium; halogen group; Cyano group; nitro group; hydroxyl group; Amine group; silyl group; boron group; Alkoxy group; Aryloxy group; Alkyl group; Cycloalkyl group; Aryl group; and a heterocyclic group, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituent.
  • substituted or unsubstituted refers to deuterium; Cyano group; Alkyl group; Cycloalkyl group; Aryl group; and a heterocyclic group, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituent.
  • substituted or unsubstituted refers to deuterium; Alkyl group; Cycloalkyl group; and an aryl group, or is substituted with a substituent in which two or more of the above-exemplified substituents are linked, or does not have any substituent.
  • halogen groups include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).
  • the silyl group may be represented by the formula -SiY a Y b Y c , where Y a , Y b and Y c are each hydrogen; Substituted or unsubstituted alkyl group; Or, it may be a substituted or unsubstituted aryl group.
  • the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. No.
  • the boron group may be represented by the chemical formula -BY dY e , where Y d and Y e are each hydrogen; Substituted or unsubstituted alkyl group; Or, it may be a substituted or unsubstituted aryl group.
  • the boron group specifically includes, but is not limited to, trimethyl boron group, triethyl boron group, t-butyldimethyl boron group, triphenyl boron group, and phenyl boron 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 60. According to one embodiment, the carbon number of the alkyl group is 1 to 30. According to another embodiment, the carbon number of the alkyl group is 1 to 20. According to another embodiment, the carbon number of the alkyl group is 1 to 10.
  • alkyl groups include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -Hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, etc., but are not limited to these.
  • the description of the alkyl group described above may be applied, except that the arylalkyl group is substituted with an aryl group.
  • 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 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n.
  • Substituents containing alkyl groups, alkoxy groups, and other alkyl group moieties described in this specification include both straight-chain or branched forms.
  • the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, styrenyl, etc., but are not limited to these.
  • the alkynyl group is a substituent containing a triple bond between carbon atoms, and may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkynyl group has 2 to 20 carbon atoms. According to another embodiment, the carbon number of the alkynyl group is 2 to 10.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 20. According to another embodiment, the carbon number of the cycloalkyl group is 3 to 6. Specifically, it includes cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, etc., but is not limited thereto.
  • the amine group is -NH 2
  • the amine group may be substituted with the above-described alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof.
  • the number of carbon atoms of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the carbon number of the amine group is 1 to 20. According to one embodiment, the carbon number of the amine group is 1 to 10.
  • substituted amine groups include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, and diphenylamine.
  • phenylpyridylamine group phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, Ditolylamine group, phenyltolylamine group, diphenylamine group, etc., but are not limited to these.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a monocyclic aryl group or a polycyclic aryl group (aryl group with two or more rings).
  • An aryl group consisting of a single ring is a phenyl group; Alternatively, it may mean a group in which two or more phenyl groups are connected.
  • the monocyclic aryl group may include, but is not limited to, a phenyl group, biphenyl group, terphenyl group, or quarterphenyl group.
  • a polycyclic aryl group may refer to a group in which two or more monocyclic rings are condensed, such as a naphthyl group or phenanthrenyl group.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure.
  • the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.
  • fluorenyl group When the fluorenyl group is substituted, , , Spirofluorenyl groups such as (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited to this.
  • the above-described description of the aryl group may be applied to the aryl group in the aryloxy group.
  • the above-described description of the alkyl group may be applied to the alkyl group among the alkylthioxy group and the alkylsulfoxy group.
  • the above-mentioned description of the aryl group may be applied to the aryl group among the arylthioxy group and the arylsulfoxy group.
  • the heterocyclic group is a cyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but it is preferably 2 to 60 carbon atoms. According to one embodiment, the carbon number of the heterocyclic group is 2 to 30. According to one embodiment, the carbon number of the heterocyclic group is 2 to 20.
  • heterocyclic groups include pyridine group, pyrrole group, pyrimidine group, quinoline group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group, and carboxymethyl group. Examples include sol group, benzocarbazole group, naphthobenzofuran group, benzonaphthothiophene group, indenocarbazole group, and triazinyl group, but are not limited to these.
  • heterocyclic group described above may be applied, except that the heteroaryl group is aromatic.
  • the description of the aryl group may be applied, except that the arylene group is divalent.
  • heteroaryl group In the present specification, the description of the heteroaryl group above can be applied, except that the heteroarylene group is divalent.
  • ring refers to a hydrocarbon ring; Or it means a heterocycle.
  • the hydrocarbon ring may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group.
  • forming a ring by combining with adjacent groups means a substituted or unsubstituted aliphatic hydrocarbon ring by combining with adjacent groups; Substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Substituted or unsubstituted aromatic heterocycle; Or it means forming a condensation ring thereof.
  • the hydrocarbon ring refers to a ring consisting only of carbon and hydrogen atoms.
  • the heterocycle refers to a ring containing one or more elements selected from N, O, P, S, Si, and Se.
  • the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle, and aromatic heterocycle may be monocyclic or polycyclic.
  • an aliphatic hydrocarbon ring refers to a non-aromatic ring consisting only of carbon and hydrogen atoms.
  • Examples of aliphatic hydrocarbon rings include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene. It is not limited to this.
  • an aromatic hydrocarbon ring refers to an aromatic ring consisting only of carbon and hydrogen atoms.
  • aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, Benzofluorene, spirofluorene, etc., but are not limited thereto.
  • an aromatic hydrocarbon ring can be interpreted to have the same meaning as an aryl group.
  • 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.
  • an aromatic heterocycle refers to an aromatic ring containing one or more heteroatoms.
  • aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, and thiazole.
  • the compound represented by Formula 1 according to the present invention is characterized in that two N-containing ring groups represented by Formula A are connected to a biphenyl containing a cyano group through a linker, and the electron mobility is increased due to the two N-containing ring groups in the molecule. It increases the efficiency of the organic light-emitting device and increases the lifespan of the organic light-emitting device by controlling the electron injection characteristics by including one cyano group in the molecule.
  • L1 and L2 are the same or different from each other and are each independently a substituted or unsubstituted arylene group
  • Ar1 and Ar2 are the same as or different from each other, and are each independently represented by the following formula A,
  • the portion of the benzene ring that does not have a substituent is substituted with hydrogen or deuterium.
  • X1 is N or CR1
  • X2 is N or CR2
  • X3 is N or CR3
  • X4 is N or CR4
  • X5 is N or CR5
  • At least two of X1 to X5 are N,
  • R1 to R5 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring,
  • L1 and L2 are the same or different from each other and are each independently a substituted or unsubstituted arylene group.
  • L1 and L2 are the same or different from each other, and are each independently a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
  • L1 and L2 are the same or different from each other, and are each independently a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L1 and L2 are the same or different from each other, and are each independently a substituted or unsubstituted arylene group having 6 to 20 carbon atoms.
  • L1 and L2 are the same or different from each other, and are each independently a substituted or unsubstituted phenylene group; Substituted or unsubstituted biphenylene group; Substituted or unsubstituted terphenylene group; Or a substituted or unsubstituted naphthylene group.
  • L1 and L2 are the same or different from each other, and are each independently a substituted or unsubstituted phenylene group; Substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene group.
  • L1 and L2 are the same or different from each other, and are each independently a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.
  • L1 and L2 are the same or different from each other, and are each independently a phenylene group substituted or unsubstituted with deuterium; Or it is a naphthylene group substituted or unsubstituted with deuterium.
  • L1 and L2 are the same or different from each other, and are each independently a phenylene group; Biphenylene group; Or it is a naphthylene group.
  • L1 and L2 are the same or different from each other and are a phenylene group; Or it is a naphthylene group.
  • L1 and L2 are the same and are substituted or unsubstituted phenylene groups.
  • L1 and L2 are the same and represent a substituted or unsubstituted naphthylene group.
  • L1 and L2 are the same or different from each other, and are each independently represented by one of the following structural formulas.
  • L1 and L2 are the same or different from each other, and are each independently represented by one of the following structural formulas.
  • L1 and L2 are the same or different from each other, and are each independently represented by one of the following structural formulas.
  • Ar1 and Ar2 are the same or different from each other, and are each independently represented by the following formula A,
  • X1 is N or CR1
  • X2 is N or CR2
  • X3 is N or CR3
  • X4 is N or CR4
  • X5 is N or CR5
  • At least two of X1 to X5 are N,
  • R1 to R5 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring,
  • X1 and X2 are N, X3 is CR3, X4 is CR4, and X5 is CR5.
  • X1 and X3 are N, X2 is CR2, X4 is CR4, and X5 is CR5.
  • X1 and X5 are N, X2 is CR2, X3 is CR3, and X4 is CR4.
  • X1, X3, and X5 are N, X2 is CR2, and X4 is CR4.
  • X1, X4, and X5 are N
  • X2 is CR2
  • X3 is CR3.
  • X1, X2, X4, and X5 are N, and X3 is CR3.
  • 2 to 4 of X1 to X5 are N.
  • two of X1 to X5 are N.
  • three of X1 to X5 are N.
  • four of X1 to X5 are N.
  • R1 to R5 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group, or adjacent groups combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring.
  • R1 to R5 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or, it is a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or adjacent groups are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 60 carbon atoms.
  • R1 to R5 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or, it is a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or adjacent groups are combined with each other to form a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • R1 to R5 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; an alkyl group having 1 to 20 carbon atoms; Cycloalkyl group having 3 to 30 carbon atoms; Aryl group having 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group, aryl group, or cycloalkyl group; or a heterocyclic group having 2 to 30 carbon atoms substituted or unsubstituted by an alkyl group, an aryl group, or a cycloalkyl group, or adjacent groups are bonded together to form an aromatic hydrocarbon having 6 to 30 carbon atoms substituted or unsubstituted by an alkyl group, an aryl group, or a cycloalkyl group. forms a ring
  • R1 to R5 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted methyl group; Substituted or unsubstituted propyl group; Substituted or unsubstituted cyclohexyl group; Substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Or it is a substituted or unsubstituted pyridyl group, or adjacent groups combine with each other to form a substituted or unsubstituted benzene ring.
  • R1 to R5 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; isopropyl group; Cyclohexyl group; A phenyl group unsubstituted or substituted with deuterium, an alkyl group, or a cycloalkyl group; Biphenyl group substituted or unsubstituted with deuterium or cyano group; Naphthyl group substituted or unsubstituted with deuterium; Or, it is a pyridyl group substituted or unsubstituted with deuterium or an alkyl group, or adjacent groups combine with each other to form a benzene ring substituted or unsubstituted with deuterium.
  • R1 to R5 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; isopropyl group; Cyclohexyl group; Deuterium, methyl group, tert-butyl group; Or a phenyl group substituted or unsubstituted with a cyclohexyl group; Biphenyl group substituted or unsubstituted with deuterium or cyano group; Naphthyl group substituted or unsubstituted with deuterium; Or, it is a pyridyl group substituted or unsubstituted with deuterium or a methyl group, or adjacent groups combine with each other to form a benzene ring substituted or unsubstituted with deuterium.
  • R1 to R5 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; methyl group; isopropyl group; Cyclohexyl group; Methyl group, tert-butyl group; Or a phenyl group substituted or unsubstituted with a cyclohexyl group; Biphenyl group substituted or unsubstituted with a cyano group; naphthyl group; Or, it is a pyridyl group substituted or unsubstituted with a methyl group, or adjacent groups combine with each other to form a benzene ring.
  • R1 to R5 are the same as or different from each other, and are each independently hydrogen; methyl group; tert-butyl group; Or a phenyl group substituted or unsubstituted with a cyano group; Biphenyl group substituted or unsubstituted with a cyano group; Or it is a pyridyl group, or adjacent groups combine with each other to form a benzene ring.
  • R3 and R4 are combined with each other to form a benzene ring.
  • R4 and R5 are combined with each other to form a benzene ring.
  • R1 to R5 when adjacent groups among R1 to R5 do not combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring, at least two of R1 to R5 are not hydrogen.
  • R1 to R5 when adjacent groups among R1 to R5 do not combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring, at least two of R1 to R5 are hydrogen; Or not deuterium.
  • R1 to R5 when adjacent groups among R1 to R5 do not combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring, at least three of R1 to R5 are not hydrogen.
  • R1 to R5 when adjacent groups among R1 to R5 do not combine with each other to form a substituted or unsubstituted aromatic hydrocarbon ring, at least three of R1 to R5 are hydrogen; Or not deuterium.
  • Formula A is represented by any one of the following structural formulas A-1 to A-8.
  • R' is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • n is an integer from 0 to 4, and when m is 2 or more, 2 or more R's are the same or different from each other,
  • Ar1 and Ar2 are the same or different from each other, and are each independently represented by any one of the structural formulas A-1 to A-8.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently represented by any one of the structural formulas A-1 to A-4, A-7, and A-8.
  • Formula 1 is represented by any one of the following Formulas 1-1 to 1-6.
  • the portion of the benzene ring that does not have a substituent is substituted with hydrogen or deuterium.
  • Formula 1 is represented by any one of the following Formulas 2-1 to 2-6.
  • Y1 is N or CR11
  • Y2 is N or CR12
  • Y3 is N or CR13
  • Y4 is N or CR14
  • Y5 is N or CR15
  • At least two of Y1 to Y5 are N,
  • R11 to R15 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • R' and R'' are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • n and n are each integers from 0 to 4, and when m and n are each 2 or more, 2 or more R' and R'' are the same or different from each other,
  • the portion of the benzene ring that does not have a substituent is substituted with hydrogen or deuterium.
  • Formula 1 is represented by any one of the following Formulas 3-1 to 3-3.
  • the portion of the benzene ring that does not have a substituent is substituted with hydrogen or deuterium.
  • Formula 1 is represented by any one of the following compounds.
  • the core structure of the compound represented by Chemical Formula 1 may be manufactured by a method such as General Formula 1 or 2 below. Substituents may be combined by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art.
  • the reaction is a Suzuki coupling reaction, and is preferably carried out in the presence of a palladium catalyst and a base, and the reactor for the Suzuki coupling reaction can be changed according to what is known in the art.
  • the manufacturing method may be further detailed in the manufacturing examples described later.
  • compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by Formula 1 above.
  • the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents into the core structure of the above structure.
  • the present specification provides an organic light-emitting device containing the above-mentioned compound.
  • the organic light emitting device includes an anode; cathode; And an organic light-emitting device comprising at least one organic material layer provided between the anode and the cathode, wherein at least one layer of the organic material layer includes a compound represented by the above-mentioned formula (1).
  • the organic light-emitting device of the present specification can be manufactured using conventional organic light-emitting device manufacturing methods and materials, except that the organic material layer is formed using the compound of Formula 1 described above.
  • the compound may be formed into an organic material 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, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
  • 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.
  • the organic light emitting device of the present invention includes one or more of the organic material layers: a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer. It may have a structure that includes However, the structure of the organic light emitting device of the present specification is not limited to this and may include fewer or more organic material 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 is a compound represented by the above-mentioned formula 1. It can be included.
  • the organic material layer includes a hole transport layer or a hole injection layer
  • the hole transport layer or the hole injection layer may include a compound represented by the above-described formula (1).
  • the organic material layer includes an electron injection layer, an electron transport layer, an electron transport and injection layer, or a hole blocking layer, and the electron injection layer, the electron transport layer, the electron transport and injection layer, or the hole blocking layer is It may include a compound represented by the above-mentioned formula (1).
  • the organic material layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer
  • the electron transport layer, an electron injection layer, or an electron transport and injection layer is represented by the above-mentioned formula (1) It may contain compounds.
  • the organic material layer includes an electron control layer
  • the electron control layer may include a compound represented by the above-described Chemical Formula 1.
  • the organic material layer includes a hole blocking layer
  • the hole blocking layer includes the compound represented by Formula 1.
  • the organic material layer is an electron transport and injection layer
  • the electron transport and injection layer includes the compound represented by the above-described formula (1).
  • the thickness of the organic material layer containing the compound of Formula 1 is 50 ⁇ to 600 ⁇ , preferably 100 ⁇ to 500 ⁇ , and more preferably 200 ⁇ to 400 ⁇ .
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by the above-described formula (1).
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by the above-described formula 1 as a host.
  • the organic material layer includes a light-emitting layer, and the light-emitting layer includes the compound represented by the above-described formula (1) as a dopant.
  • the organic layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Formula 1 described above.
  • the light emitting layer further includes a fluorescent dopant or a phosphorescent dopant.
  • the dopant in the light emitting layer is included in an amount of 1 to 50 parts by weight based on 100 parts by weight of the host.
  • the organic layer includes a light-emitting layer
  • the light-emitting layer includes the compound represented by Formula 1 as a host, and may further include an additional host.
  • the dopant includes an arylamine-based compound, a heterocyclic compound containing boron and nitrogen, or an Ir complex.
  • the organic light emitting device of the present specification may further include one or more organic material layers among a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer. You can.
  • the organic light emitting device includes an anode; cathode; and two or more organic layers provided between the anode and the cathode, wherein at least one of the two or more organic layers includes the compound represented by Formula 1.
  • the two or more organic layers may be selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a hole transport and injection layer, and an electron blocking layer.
  • the two or more organic layers may be selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron control layer, and a hole blocking layer.
  • the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound represented by Formula 1.
  • the compound represented by Formula 1 may be included in one of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
  • the organic layer containing the compound represented by Formula 1 is an electron transport layer, an electron injection layer, or an electron transport and injection layer
  • the electron transport layer, the electron injection layer, or the electron transport and injection layer is an n-type dopant or an organic metal compound. It may further include.
  • the n-type dopant or organometallic compound may be one known in the art, for example, a metal or a metal complex.
  • the n-type dopant or organometallic compound may be LiQ, but is not limited thereto.
  • the electron transport layer, electron injection layer, or electron transport and injection layer containing the compound represented by Formula 1 may further include LiQ (Lithium Quinolate).
  • the compound represented by Formula 1 and the n-type dopant or organometallic compound may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4. According to one example, the compound represented by Formula 1 and the n-type dopant or organometallic compound may be included in a weight ratio of 1:1.
  • the organic layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes the compound represented by Formula 1.
  • the compound represented by Formula 1 may be included in one of the two or more hole transport layers, and may be included in each of the two or more hole transport layers.
  • the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamine group, carbazolyl group, or benzocarbazolyl group in addition to the organic material layer including the compound represented by Formula 1. It can be included.
  • 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.
  • the organic material layer may include an electron blocking layer, and materials known in the art may be used as the electron blocking layer.
  • the organic light emitting device may have, for example, a stacked structure as shown below, but is not limited thereto.
  • the structure of the organic light emitting device of the present specification may have the same structure as shown in FIGS. 1 to 4, but is not limited thereto.
  • Figure 1 shows an example of an organic light-emitting device in which a substrate 1, an anode 2, an organic material layer 10, and a cathode 9 are sequentially stacked.
  • the compound may be included in the light-emitting layer 5.
  • Figure 2 shows the substrate (1), anode (2), hole injection layer (3), hole transport layer (4), light emitting layer (5), electron transport layer (6), electron injection layer (7), and cathode (9) sequentially.
  • An example of a stacked organic light emitting device is shown.
  • the compound may be included in the hole injection layer (3), the hole transport layer (4), the light emitting layer (5), the electron transport layer (6), or the electron injection layer (7).
  • FIG. 3 shows a substrate (1), anode (2), hole injection layer (3), first hole transport layer (4-1), second hole transport layer (4-2), light emitting layer (5), and electron transport and injection layer.
  • This shows an example of an organic light emitting device in which (8) and a cathode (9) are sequentially stacked.
  • the compound is used in the hole injection layer (3), the first hole transport layer (4-1), the second hole transport layer (4-2), the light emitting layer (5), or the electron transport and injection layer (8). may be included in
  • Figure 4 shows an organic structure in which a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), light emitting layer (5), electron transport and injection layer (8), and cathode (9) are sequentially stacked.
  • a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), light emitting layer (5), electron transport and injection layer (8), and cathode (9) are sequentially stacked.
  • An example of a light emitting device is shown.
  • the compound may be included in the hole injection layer 3, the hole transport layer 4, the light emitting layer 5, or the electron transport and injection layer 8.
  • the electron transport and injection layer and the light emitting layer may be provided adjacent to each other.
  • the electron transport layer and the light emitting layer may be provided adjacent to each other.
  • the electron control layer and the light emitting layer may be provided adjacent to each other.
  • the hole blocking layer and the light emitting layer may be provided adjacent to each other.
  • the hole blocking layer and the electron transport layer may be provided adjacent to each other.
  • the organic light emitting device of the present specification can be manufactured using materials and methods known in the art, except that at least one layer of the organic material layer contains the above compound, that is, the compound represented by Chemical Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device uses a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to deposit a metal, a conductive metal oxide, or an alloy thereof on a substrate.
  • a PVD physical vapor deposition
  • an organic material layer including a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer thereon, and then depositing a material that can be used as a cathode on it. It can be.
  • 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 organic layer may further include one or more of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.
  • the organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, but is not limited to this and may have a single-layer structure. You can.
  • the organic material layer uses a variety of polymer materials to form a smaller number of layers by using a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer. It can be manufactured in layers.
  • the anode is an electrode that injects holes
  • the anode material is generally preferably a material with a large work function to ensure smooth hole injection into the organic layer.
  • anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); Combination of metal and oxide such as ZnO:Al or SnO 2 :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 to these.
  • the cathode is an electrode that injects electrons
  • the cathode material is generally preferably a material with a small work function to facilitate electron injection into the organic layer.
  • Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof;
  • There are multi-layer structure materials such as LiF/Al or LiO 2 /Al, but they are not limited to these.
  • the hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage.
  • the hole injection material is HOMO (highest occupied). It is preferable that the molecular orbital is between the work function of the anode material and the HOMO of the surrounding organic layer.
  • Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrilehexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based organic substances.
  • the thickness of the hole injection layer may be 1 nm to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage in preventing the hole injection characteristics from being deteriorated. If the thickness of the hole injection layer is 150 nm or less, the thickness of the hole injection layer is too thick to improve the movement of holes. There is an advantage in preventing it from rising.
  • the hole injection layer may include a diamine compound containing an aryl group or heteroaryl group.
  • the amine compound may have a structure in which an amine group is bonded to a spiroacridine fluorene structure.
  • the hole transport layer may play a role in facilitating the transport of holes.
  • the hole transport material is a material that can transport holes from the anode or hole injection layer and transfer them to the light emitting layer, and a material with high mobility for holes is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers with both conjugated and non-conjugated portions, but are not limited to these.
  • the hole transport layer may include one or more N-containing polycyclic compounds containing a cyano group or an amine compound containing a carbazole group.
  • the N-containing polycyclic compound may be 1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile (HATCN).
  • HATCN 1,4,5,8,9,11-Hexaazatriphenylenehexacarbonitrile
  • the hole transport layer may include the above compounds alone or may include two or more types of compounds.
  • the HATCN may be deposited and used as a first hole transport layer, and an amine compound containing the carbazole group may be deposited thereon and used as a second hole transport layer.
  • An additional hole buffer layer may be provided between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
  • the above-described compounds or materials known in the art may be used in the electron blocking layer.
  • the light-emitting layer may emit red, green, or blue light and may be made of a phosphorescent material or a fluorescent material.
  • the light-emitting material is a material capable of emitting light in the visible range by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and is preferably a material with good quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Compounds of the benzoxazole, benzthiazole and benzimidazole series; Poly(p-phenylenevinylene) (PPV) series polymer; Spiro compounds; Polyfluorene, rubrene, etc., but are not limited to these.
  • Alq 3 8-hydroxy-quinoline aluminum complex
  • Carbazole-based compounds dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compound
  • Compounds of the benzoxazole, benzthiazole and benzimidazole series Compounds of the benzoxazole, benzthiazole and benzimidazole series
  • Poly(p-phenylenevinylene) (PPV) series polymer Poly(p-phenylenevinylene) (PPV) series polymer
  • Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocycle-containing compounds.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include, but are not limited to, furan compounds and pyrimidine derivatives.
  • the light-emitting dopants include PIQIr(acac)(bis(1-phenylsoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), and PQIr(tris(1-phenylquinoline)iridium).
  • phosphorescent materials such as PtOEP (octaethylporphyrin platinum), or fluorescent materials such as Alq 3 (tris(8-hydroxyquinolino)aluminum) may be used, but are not limited to these.
  • a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) can be used as the light-emitting dopant.
  • a phosphor such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum)
  • Alq3 tris(8-hydroxyquinolino)aluminum
  • the light-emitting dopant may be a phosphorescent material such as (4,6-F2ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited to these.
  • the light-emitting layer may include an anthracene compound substituted with an aryl group or a heterocyclic group as a host, and a pyrene compound substituted with an amine group as a dopant.
  • the anthracene compound may have a structure in which carbons 9 and 10 are substituted with an aryl group or heterocyclic group.
  • the host and the dopant may be included in an appropriate weight ratio. According to one example, the host and the dopant may be included in a weight ratio of 100:1 to 100:10, respectively.
  • a hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.
  • the electron transport layer may play a role in facilitating the transport of electrons.
  • 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 suitable. Specific examples include the above-mentioned compounds or Al complex of 8-hydroxyquinoline; Complex containing Alq 3 ; organic radical compounds; Hydroxyflavone-metal complexes, etc., but are not limited to these.
  • the thickness of the electron transport layer may be 1 nm to 50 nm.
  • the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing the electron transport characteristics from deteriorating, and if it is 50 nm or less, the thickness of the electron transport layer is too thick, so the driving voltage is increased to improve the movement of electrons. There is an advantage to preventing it.
  • the electron transport layer may include a compound represented by Formula 1 of the present invention, and may further include an n-type dopant or an organometallic compound.
  • the n-type dopant or organometallic compound may be LiQ
  • the compound represented by Formula 1 of the present invention and the n-type dopant (or organometallic compound) are 2:8 to 8:2, for example, 4: It may be included in a weight ratio of 6 to 6:4.
  • the electron injection layer may serve to facilitate injection of electrons.
  • the electron injection material has the ability to transport electrons, has an excellent electron injection effect from the cathode, the light emitting layer or the light emitting material, prevents the movement of excitons generated in the light emitting layer to the hole injection layer, and also has an excellent electron injection effect to the light emitting layer or light emitting material.
  • Compounds with excellent thin film forming ability are preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone, etc. and their derivatives, metals. These include, but are not limited to, complex compounds and nitrogen-containing five-membered ring derivatives.
  • metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, 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. It is not limited to this.
  • 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 hole injection layer. Specifically, it includes oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, etc., 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.
  • E1-A (20 g, 59.3 mmol) and E1-B (48.4 g, 118.6 mmol) were added to 400 ml of tetrahydrofuran, stirred, and refluxed. Afterwards, potassium carbonate (24.6 g, 178 mmol) was dissolved in 25 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (2.1 g, 1.8 mmol) was added. After reacting for 3 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • Compound E2 was prepared in the same manner as in Synthesis Example 1, except that each starting material was prepared according to the above reaction scheme.
  • Compound E3 was prepared in the same manner as in Synthesis Example 1, except that each starting material was used according to the above reaction scheme.
  • Compound E4 was prepared in the same manner as in Synthesis Example 1, except that each starting material was used according to the above reaction formula.
  • Compound E5 was prepared in the same manner as in Synthesis Example 1, except that each starting material was prepared according to the above reaction scheme.
  • Compound E6 was prepared in the same manner as in Synthesis Example 1, except that each starting material was used according to the above reaction scheme.
  • Compound E7 was prepared in the same manner as in Synthesis Example 1, except that each starting material was used according to the above reaction scheme.
  • Compound E8 was prepared in the same manner as in Synthesis Example 1, except that each starting material was prepared according to the above reaction scheme.
  • Compound E9 was prepared in the same manner as in Synthesis Example 1, except that each starting material was prepared according to the above reaction scheme.
  • Compound E10 was prepared in the same manner as in Synthesis Example 1, except that each starting material was used according to the above reaction scheme.
  • Compound E11 was prepared in the same manner as in Synthesis Example 1, except that each starting material was used according to the above reaction scheme.
  • E12-A (20 g, 50.4 mmol) and E12-B (16.3 g, 50.4 mmol) were added to 400 ml of tetrahydrofuran, stirred, and refluxed. Afterwards, potassium carbonate (20.9 g, 151.2 mmol) was dissolved in 21 ml of water, stirred sufficiently, and then tetrakistriphenyl-phosphinopalladium (1.7 g, 1.5 mmol) was added. After reacting for 2 hours, the mixture was cooled to room temperature, the organic layer and the water layer were separated, and the organic layer was distilled.
  • Compound E13 was prepared in the same manner as in Synthesis Example 12, except that each starting material was used according to the above reaction scheme.
  • Compound E14 was prepared in the same manner as in Synthesis Example 12, except that each starting material was prepared according to the above reaction scheme.
  • Compound E15 was prepared in the same manner as in Synthesis Example 12, 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) with a thickness of 1,000 ⁇ was placed in distilled water with a detergent dissolved in it and washed ultrasonically.
  • a detergent from Fischer Co. was used, and distilled water filtered secondarily using a filter from Millipore Co. was used as distilled water.
  • 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.
  • hole injection layer hexanitrile hexaazatriphenylene (HAT, 50 ⁇ ) of the following formula and HT-A (600 ⁇ ) of the following compound were sequentially vacuum deposited to form a hole transport layer.
  • HAT hexanitrile hexaazatriphenylene
  • the following compounds BH and BD were vacuum deposited at a weight ratio of 25:1 to a film thickness of 200 ⁇ on the hole transport layer to form a light emitting layer.
  • compound E1 prepared in Synthesis Example 1 and the following compound [LiQ] (Lithiumquinolate) were vacuum deposited at a 1:1 weight ratio to form an electron transport and injection layer with a thickness of 360 ⁇ .
  • a cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 10 ⁇ and aluminum to a thickness of 1,000 ⁇ on the electron transport and injection layer.
  • the deposition rate of organic matter was maintained at 0.4 ⁇ 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 degree during deposition was 1 ⁇ 10.
  • An organic light emitting device was manufactured by maintaining -7 to 5 ⁇ 10 -8 torr.
  • An organic light-emitting device was manufactured in the same manner as Experiment 1, except that the compound shown in Table 1 below was used instead of Compound E1 of Experiment 1.
  • An organic light-emitting device was manufactured in the same manner as Experiment 1, except that the compound shown in Table 1 below was used instead of Compound E1 of Experiment 1.
  • the compounds ET-1 to ET-8 used in Table 1 below are as follows.
  • the driving voltage, luminous efficiency and color coordinates were measured at a current density of 10 mA/cm 2 and at a current density of 20 mA/cm 2
  • the time (T 90 ) for the current density to reach 90% of the initial luminance was measured.
  • Table 1 The results are shown in Table 1 below.
  • the organic light emitting device using the compound represented by Formula 1 of the present invention exhibits excellent characteristics in terms of voltage, efficiency, and/or lifespan (T 90 ).
  • the compound represented by Formula 1 of the present invention is characterized in that an N-containing ring group represented by Formula A is connected to a benzene ring containing a cyano group through a linker, and electron mobility is increased due to two N-containing ring groups in the molecule.
  • the efficiency of the organic light emitting device is increased by increasing, and the N-containing ring group is connected through a linker rather than directly connected to the parent nucleus structure, thereby forming LUMO energy desirable as an electron transport and injection layer, thereby increasing the electron injection effect into the light emitting layer.
  • the results showed that the lifespan of the organic light-emitting device was increased by controlling the electron injection characteristics by including one cyano group in the molecule.
  • the organic light-emitting device containing the compound of Formula 1 of the present invention has significantly better characteristics in terms of efficiency and lifespan than the case with one N-containing ring group. It was confirmed that .
  • the organic light-emitting device containing the compound of Formula 1 of the present invention has better efficiency and lifespan than the compound in which the biphenylene group is unsubstituted with a cyano group. It was confirmed that it showed significantly excellent characteristics.
  • the organic light-emitting device containing the compound of Formula 1 of the present invention has higher efficiency than the compound whose parent core structure is substituted with naphthalene rather than biphenylene, It was confirmed that it showed significantly excellent characteristics in terms of lifespan.
  • the organic light-emitting device containing the compound of Formula 1 of the present invention has better efficiency and lifespan than the compound in which the N-containing ring group represented by Formula A is directly connected. It was confirmed that it showed significantly excellent characteristics.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé représenté par la formule chimique 1 et un dispositif électroluminescent organique comprenant le composé.
PCT/KR2023/003332 2022-03-10 2023-03-10 Composé et élément électroluminescent organique le comprenant WO2023172112A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160126862A (ko) * 2015-04-24 2016-11-02 주식회사 엘지화학 유기 발광 소자
KR20180111482A (ko) * 2017-03-30 2018-10-11 주식회사 엘지화학 유기발광 소자
KR20190038110A (ko) * 2017-09-29 2019-04-08 삼성에스디아이 주식회사 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치
KR20200038169A (ko) * 2018-10-02 2020-04-10 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기발광 소자
CN111072637A (zh) * 2019-12-27 2020-04-28 吉林奥来德光电材料股份有限公司 有机发光化合物、其制备方法及有机发光器件
CN114014742A (zh) * 2021-11-01 2022-02-08 上海八亿时空先进材料有限公司 一种三芳基苯衍生物、发光材料、发光元件及消费型产品

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160126862A (ko) * 2015-04-24 2016-11-02 주식회사 엘지화학 유기 발광 소자
KR20180111482A (ko) * 2017-03-30 2018-10-11 주식회사 엘지화학 유기발광 소자
KR20190038110A (ko) * 2017-09-29 2019-04-08 삼성에스디아이 주식회사 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치
KR20200038169A (ko) * 2018-10-02 2020-04-10 주식회사 엘지화학 신규한 화합물 및 이를 포함하는 유기발광 소자
CN111072637A (zh) * 2019-12-27 2020-04-28 吉林奥来德光电材料股份有限公司 有机发光化合物、其制备方法及有机发光器件
CN114014742A (zh) * 2021-11-01 2022-02-08 上海八亿时空先进材料有限公司 一种三芳基苯衍生物、发光材料、发光元件及消费型产品

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