WO2024117844A1 - Compound and organic light-emitting element containing same - Google Patents

Compound and organic light-emitting element containing same Download PDF

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WO2024117844A1
WO2024117844A1 PCT/KR2023/019646 KR2023019646W WO2024117844A1 WO 2024117844 A1 WO2024117844 A1 WO 2024117844A1 KR 2023019646 W KR2023019646 W KR 2023019646W WO 2024117844 A1 WO2024117844 A1 WO 2024117844A1
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group
substituted
unsubstituted
compound
formula
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PCT/KR2023/019646
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French (fr)
Korean (ko)
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차용범
금수정
조우진
최지영
하재승
황성현
이우철
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주식회사 엘지화학
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K99/00—Subject matter not provided for in other groups of this subclass

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.
  • the present application seeks to provide a compound and an organic light-emitting device containing the same.
  • B is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • R1 to R16, R25 and R26 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and d is an integer of 0 to 2,
  • R21 to R24 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.
  • Another embodiment of the present specification is an anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one layer of the organic material layer contains the compound.
  • the compound according to an exemplary embodiment of the present invention can be used as a material for the organic layer of an organic light-emitting device.
  • the compound according to a specific embodiment of the present invention can be used as a material for the light-emitting layer of an organic light-emitting device.
  • the compound according to an exemplary embodiment of the present invention can be included in an organic light emitting device to improve device characteristics such as low driving voltage, excellent efficiency characteristics, or excellent lifespan characteristics.
  • FIG. 1 to 3 show examples of organic light-emitting devices according to some embodiments of the present invention.
  • the deuterium substitution rate of the compound is determined by using TLC-MS (Thin-Layer Chromatography/Mass Spectrometry), and is determined by maximizing the distribution of molecular weights at the end of the reaction.
  • a method of calculating the substitution rate based on the value or a quantitative analysis method using NMR can be determined by adding DMF as an internal standard and calculating the D-substitution rate from the integral amount of the total peak using the integration rate on 1H NMR. You can.
  • 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; Nitrile 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; 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.
  • 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; Nitrile group; silyl group; Alkoxy group; Aryloxy group; Alkyl 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; 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.
  • halogen groups include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).
  • the silyl group may be represented by the formula -SiYaYbYc, where Ya, Yb, and Yc 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 -BYdYe, where Yd and Ye 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, dimethyl boron group, diethyl boron group, t-butyldimethyl boron group, diphenyl 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 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.
  • 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, stilbenyl group, styrenyl group, etc., but are not limited to these.
  • 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 such as a phenyl group, biphenyl group, terphenyl group, or quarterphenyl group, but is not limited thereto.
  • 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.
  • 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 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 can 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.
  • ring is a hydrocarbon ring; Or refers to a heterocycle.
  • the hydrocarbon ring may be an 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 heteroatoms 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 according to an exemplary embodiment of the present specification is represented by Formula 1 as described above.
  • the compound of Formula 1 is characterized in that a biphenyl group substituted with dibenzofuran and B are substituted at carbons 9 and 10 of anthracene, respectively, where dibenzofuran is characterized in that it is bonded to the ortho position of biphenyl. . Due to these structural characteristics, when the compound is applied to an organic light emitting device, it can exhibit low voltage, high efficiency, and/or long life effects.
  • Formula 1 may be represented by any one of the following Formulas 21 to 23.
  • R21 to R26 are hydrogen; Or deuterium.
  • B is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a group of the following formula (11).
  • X is O or S
  • R17 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • a and b are each 0 or 1
  • c is an integer from 0 to 12
  • B is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted naphthobenzofuran group; Or a substituted or unsubstituted naphthobenzothiophene group.
  • B has a deuterium substitution rate of 0%.
  • B has a deuterium substitution rate of 10% to 100%.
  • B has a deuterium substitution rate of 20% to 100%.
  • B has a deuterium substitution rate of 50% to 100%.
  • B is a structure in which one or more of the following structures are connected, and the following structures are substituted or unsubstituted with deuterium.
  • R1 to R16 are each hydrogen; Or deuterium.
  • R1 to R8 are hydrogen.
  • R1 to R8 are deuterium.
  • R9 to R16 are hydrogen.
  • R9 to R16 are deuterium.
  • the deuterium substitution rate of the compound of Formula 1 is 0%.
  • the deuterium substitution rate of the compound of Formula 1 is 10% to 100%.
  • the deuterium substitution rate of the compound of Formula 1 is 20% to 100%.
  • the deuterium substitution rate of the compound of Formula 1 is 50% to 100%.
  • the compound is any one selected from the following structures.
  • An exemplary embodiment of the present specification includes an anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one layer of the organic material layer contains the compound.
  • the organic light emitting device includes an anode; cathode; and at least one organic material layer including a light-emitting layer provided between the anode and the cathode, and at least one layer of the organic material layer includes the compound of 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 one or more organic material layers are formed using the above-described compounds.
  • the thickness of the organic material layer containing the compound of Formula 1 is 10 ⁇ to 600 ⁇ , preferably 50 ⁇ to 500 ⁇ , and more preferably 200 ⁇ to 400 ⁇ .
  • 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 light emitting device of the present specification can be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. It can be manufactured by forming an anode, forming an organic material layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • PVD physical vapor deposition
  • an organic light-emitting device can be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound of Formula 1 may be formed 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 to these.
  • the organic material layer 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 material layer includes 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, and an electron injection and transport layer. It may be a multi-layered structure including: However, the structure of the organic light emitting device is not limited to this and may include fewer or more organic material layers.
  • the organic material layer may be formed of the same material or a different material.
  • 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 organic material layer containing the compound of Formula 1 may be a light-emitting layer.
  • the light-emitting layer containing the compound of Formula 1 may include only a single material, but may also include additional materials.
  • the compound of Formula 1 may serve as a host in the light-emitting layer, and in this case, it may further include an additional dopant.
  • the light-emitting layer further includes a fluorescent dopant or a phosphorescent dopant.
  • the dopant is a phosphorescent material such as (4,6-F 2 ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), PFO-based polymer, Fluorescent materials such as PPV-based polymers, anthracene-based compounds, pyrene-based compounds, boron-based compounds, etc. may be used, but are not limited thereto.
  • a phosphorescent material such as (4,6-F 2 ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), PFO-based polymer, Fluorescent materials such as PPV-based polymers, anthracene-based compounds, pyrene-based compounds, boron-based compounds, etc. may be used, but are not limited thereto.
  • 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 material layer includes a hole blocking layer, an electron transport layer, or an electron injection layer.
  • the hole blocking layer, electron transport layer, or electron injection layer may or may not include the compound.
  • the organic material layer includes a hole injection layer, a hole transport layer, or an electron blocking layer.
  • the hole injection layer, hole transport layer, or electron blocking layer may or may not include the compound.
  • the organic light emitting device includes an anode; cathode; and a light-emitting layer provided between the anode and the cathode, and further comprising a single-layer organic material layer between the light-emitting layer and the anode, wherein the light-emitting layer includes the compound.
  • the organic light emitting device includes an anode; cathode; and a light-emitting layer provided between the anode and the cathode, and further comprising a multi-layer organic material layer between the light-emitting layer and the anode, wherein the light-emitting layer includes the compound.
  • the organic light emitting device includes an anode; cathode; and a light-emitting layer provided between the anode and the cathode, and further comprising at least one of a hole injection layer, a hole transport layer, and an electron blocking layer between the light-emitting layer and the anode, and the light-emitting layer includes the compound.
  • the organic light emitting device includes an anode; cathode; and a light-emitting layer provided between the anode and the cathode, and a hole injection layer, a hole transport layer, and an electron blocking layer between the anode and the light-emitting layer, and the light-emitting layer includes the compound.
  • the organic light emitting device includes an anode; hole injection layer; Hole transport layer; Electronic blocking layer; light emitting layer; and a cathode are sequentially provided, and the light-emitting layer includes the compound.
  • an additional organic material layer may be further provided between each of the layers.
  • the organic light emitting device includes an anode; cathode; and a light-emitting layer provided between the anode and the cathode, and further comprising a single-layer organic material layer between the light-emitting layer and the cathode, wherein the light-emitting layer includes the compound.
  • the organic light emitting device includes an anode; cathode; and a light-emitting layer provided between the anode and the cathode, and further comprising a multi-layer organic material layer between the light-emitting layer and the cathode, wherein the light-emitting layer includes the compound.
  • the organic light emitting device includes an anode; cathode; and a light-emitting layer provided between the anode and the cathode, further comprising one or more layers of a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer between the cathode and the light-emitting layer, wherein the light-emitting layer contains the compound.
  • the organic light emitting device includes an anode; cathode; and a light-emitting layer provided between the anode and the cathode, and a hole blocking layer and an electron injection and transport layer between the cathode and the light-emitting layer, and the light-emitting layer includes the compound.
  • the organic light emitting device includes an anode; light emitting layer; hole blocking layer; electron injection and transport layer; and a cathode are sequentially provided, and the light-emitting layer includes the compound.
  • an additional organic material layer may be further provided between each of the layers.
  • the organic light emitting device includes an anode; hole injection layer; Hole transport layer; Electronic blocking layer; light emitting layer; hole blocking layer; electron injection and transport layer; and a cathode are sequentially stacked, and the light-emitting layer includes the compound.
  • the structure of the organic light emitting device of the present specification may have the same structure as shown in FIGS. 1 to 3, but is not limited thereto.
  • Figure 1 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • Figure 2 shows an example of an organic light emitting device consisting of a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), light emitting layer (7), electron transport layer (8), and cathode (4). It was done.
  • Figure 3 shows a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), electron blocking layer (9), light emitting layer (7), hole blocking layer (10), electron injection and transport layer ( 11) and an example of an organic light emitting device connected to a cathode 4 are shown.
  • the organic light emitting device may have a stacked structure, for example, as shown below, in addition to the structure specified in the drawings, but is not limited thereto.
  • the ‘electron transport layer/electron injection layer’ may be replaced with an ‘electron injection and transport layer’ or a ‘layer that performs electron injection and electron transport simultaneously’.
  • (15) may be an organic light emitting device having a stacking order of 'anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron injection and transport layer/cathode'.
  • the 'hole injection layer/hole transport layer' may be replaced with a 'hole injection and transport layer' or a 'layer that performs hole injection and hole transport at the same time'.
  • (15) may be an organic light emitting device having a stacking order of 'anode/hole injection and transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode'.
  • 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.
  • Specific examples of 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); Combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, 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 that can be used in the present invention include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are, but are not limited to, multi-layered materials such as LiF/Al or LiO 2 /Al.
  • the hole injection layer may serve to facilitate the injection of holes from the anode to the light emitting layer.
  • the hole injection material is a material that can easily inject holes from an anode at a low voltage, and it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode and the HOMO of the surrounding organic material layer.
  • Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine series compounds, hexanitrilehexaazatriphenylene series compounds, quinacridone series compounds, and perylene series. compounds, benzonitrile-based compounds, anthraquinone, and polyaniline- and polythiophene-based conductive polymers, but are not limited to these.
  • the hole injection layer may be an arylamine-based compound or a benzonitrile-based compound. More specifically, arylamine-based compounds substituted with carbazole groups and benzonitrile-based compounds substituted with halogen groups may be used, but are not limited to these.
  • 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 deteriorating, and if it is 150 nm or less, the thickness of the hole injection layer is so thick that the driving voltage is increased to improve the movement of holes. There is an advantage to preventing this.
  • the hole injection layer includes a compound of the following formula HI-1.
  • L101 is directly bonded; Or a substituted or unsubstituted arylene group,
  • R101 to R103 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group.
  • L101 is a direct bond; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.
  • L101 is a direct bond; Or a substituted or unsubstituted phenylene group.
  • L101 is a direct bond; Or it is a phenylene group.
  • R101 to R103 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic aryl group; Or it is a substituted or unsubstituted polycyclic aryl group.
  • R101 to R103 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted pyrene group; Or a substituted or unsubstituted fluorenyl group.
  • R101 to R103 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted fluorenyl group.
  • R101 to R103 are the same as or different from each other, and are each independently a phenyl group; Biphenyl group; Or it is a fluorenyl group substituted with an alkyl group.
  • the formula HI-1 is one of the following structures.
  • the hole injection layer includes a compound of the following formula HI-2.
  • R111 to R113 are the same or different from each other, and are each independently hydrogen; halogen group; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • a111 to a113 are each integers from 1 to 5
  • R111 to R113 are the same as or different from each other, and are each a halogen group; Or it is a nitrile group.
  • R111 to R113 are the same or different from each other, and are each fluorine; Or it is a nitrile group.
  • the chemical formula HI-2 has the following structure.
  • the hole injection layer includes a compound of the formula HI-1 and a compound of the formula HI-2.
  • 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 of hole transport materials include, but are not limited to, arylamine-based compounds, carbazole-based compounds, conductive polymers, and block copolymers with both conjugated and non-conjugated parts.
  • a carbazole-based compound substituted with an arylamine group may be used in the hole transport layer, but is not limited thereto.
  • the hole transport layer includes a compound of the following formula HT-1.
  • L201 and L202 are the same or different from each other and are each independently directly bonded; Or a substituted or unsubstituted arylene group,
  • R200 is a substituted or unsubstituted aryl group
  • R201 to R204 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.
  • L201 and L202 are the same or different from each other and are each independently a substituted or unsubstituted arylene group.
  • L201 and L202 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.
  • L201 and L202 are the same or different from each other and are each independently a substituted or unsubstituted phenylene group.
  • L201 and L202 are each a phenylene group.
  • R200 is a substituted or unsubstituted monocyclic aryl group; Or it is a substituted or unsubstituted polycyclic aryl group.
  • R200 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted pyrene group; Or a substituted or unsubstituted fluorenyl group.
  • R200 is a substituted or unsubstituted naphthyl group.
  • R201 to R204 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group.
  • R201 to R204 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic aryl group; Or it is a substituted or unsubstituted polycyclic aryl group.
  • R201 to R204 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted pyrene group; Or a substituted or unsubstituted fluorenyl group.
  • R201 to R204 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group.
  • R201 to R204 are each a phenyl group.
  • the chemical formula HT-1 has the following structure.
  • 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.
  • a carbazole-based compound may be used in the electron blocking layer.
  • the electron blocking layer includes a compound of the following formula EB-1.
  • L301 is a substituted or unsubstituted arylene group
  • R301 and R302 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group.
  • L301 is a monocyclic or polycyclic arylene group.
  • L301 is a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.
  • L301 is a biphenylene group.
  • R301 and R302 are the same or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted pyrene group; Or a substituted or unsubstituted fluorenyl group.
  • R301 and R302 are the same or different from each other, and are each independently a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.
  • R301 and R302 are the same or different from each other, and each independently represents a biphenyl group substituted or unsubstituted by an aryl group.
  • the formula EB-1 has the following structure.
  • 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.
  • the light-emitting material includes 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 is 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) (PP
  • 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 furan compounds and pyrimidine derivatives, but are not limited to these.
  • the compound of Formula 1 of the present invention may be used as the host of the light-emitting layer, but is not limited thereto.
  • the light-emitting dopants include PIQIr(acac)(bis(1-phenylquinoline)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.
  • the light-emitting layer emits green light
  • a phosphor such as Ir(ppy) 3 (tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum)
  • the light-emitting dopant may be a phosphorescent material such as (4,6-F 2 ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), or distrylarylene (DSA).
  • pyrene-based compounds may be used, but are not limited to these.
  • a pyrene-based compound may be used as the dopant, but is not limited thereto.
  • the dopant includes a compound of formula D below.
  • X1 and X2 are the same or different from each other and are each independently CR'; or NR", and at least one of X1 and X2 is NR",
  • R401 to R403, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; halogen group; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkoxy A substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group;
  • a substituted or unsubstituted ring is the same or different from each other, and are each independently hydrogen; deuterium; halogen group; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkoxy A substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a
  • r401 and r403 are each an integer from 0 to 4, r402 is an integer from 0 to 3, and when r401 to r403 are each 2 or more, the substituents in the parentheses are the same or different from each other.
  • R401 to R403 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.
  • R401 to R403 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted alkyl group.
  • R401 to R403 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a straight chain or branched alkyl group.
  • R401 to R403 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A straight-chain alkyl group having 1 to 30 carbon atoms; Or it is a branched alkyl group having 4 to 30 carbon atoms.
  • R401 to R403 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a branched alkyl group having 4 to 30 carbon atoms.
  • X1 and X2 are the same or different from each other and are each independently NR'', and R'' is a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.
  • X1 and X2 are the same or different from each other and are each independently NR'', and R'' is a substituted or unsubstituted aryl group.
  • X1 and X2 are the same or different from each other and are each independently NR'', and R'' is an aryl group substituted with an alkyl group.
  • Formula D has the following structure.
  • the light-emitting layer includes the compound of Formula 1 as a host of the light-emitting layer, and the compound of Formula D as a dopant of the light-emitting layer.
  • the weight ratio of the compound of Formula 1 and the compound of Formula D in the light emitting layer is 100:1 to 1:1. Specifically, 70:1 to 2:1, or 50:1 to 3:1.
  • a hole blocking layer may be provided between the cathode and the light emitting layer.
  • 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.
  • Specific examples of hole blocking materials include, but are not limited to, oxadiazole derivatives, triazole derivatives, triazine derivatives, phenanthroline derivatives, BCP, and aluminum complexes.
  • triazine derivatives may be used, but are not limited thereto.
  • the hole blocking layer includes a compound of the following formula HB-1.
  • L501 to L503 are the same or different from each other and are each independently directly bonded; Or a substituted or unsubstituted arylene group,
  • R501 to R504 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.
  • L501 to L503 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted phenylene group; Substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene group.
  • L501 to L503 are the same or different from each other and are each independently directly bonded; Or a substituted or unsubstituted biphenylene group.
  • L501 and L502 are the same or different from each other and are each independently a direct bond.
  • L503 is a substituted or unsubstituted biphenylene group.
  • L503 is a biphenylene group.
  • R501 to R504 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group.
  • R501 to R504 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic aryl group; Or it is a substituted or unsubstituted polycyclic aryl group.
  • R501 to R504 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted pyrene group; Or a substituted or unsubstituted fluorenyl group.
  • R501 to R504 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.
  • R501 to R504 are the same as or different from each other, and each independently represents a phenyl group substituted or unsubstituted by a naphthyl group.
  • the formula HB-1 is one of the following structures.
  • 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.
  • the electron transport material includes, but is not limited to, an Al complex of 8-hydroxyquinoline, a complex containing Alq 3 , an organic radical compound, and a hydroxyflavone-metal complex.
  • 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, it has the advantage of 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 to prevent the driving voltage from increasing to improve the movement of electrons. There is an advantage.
  • 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, a light emitting layer or a light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, and thin film Compounds with excellent forming ability are preferred.
  • the electron injection materials include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, triazine, imidazole, perylenetetracarboxylic acid, and preorenylidene methane. , anthrone, etc. and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives, etc., but are not limited thereto.
  • 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 electron transport layer and electron injection layer may be formed as a single layer.
  • an electron injection and transport layer can be formed by vacuum depositing an electron injection material and an electron transport material at the same time, or by vacuum depositing a material that exhibits both electron injection and transport effects.
  • the electron injection and transport layer may further include a metal complex.
  • the metal complex include, but are not limited to, Al complex of 8-hydroxyquinoline (Alq 3 ), LiQ, and metal complex compounds.
  • the electron injection and transport layer may be made of triazine derivatives and lithium quinolite (LiQ), but is not limited thereto.
  • the organic light emitting device may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
  • the organic light emitting device can be included and used in various electronic devices.
  • the electronic device may be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 1,000 ⁇ was placed in distilled water with a detergent dissolved in it and washed ultrasonically.
  • a detergent manufactured by Fischer Co. was used, and distilled water filtered secondarily using a filter manufactured by Millipore Co. was used as distilled water.
  • ultrasonic cleaning was repeated twice with distilled water for 10 minutes.
  • the following compounds HI1 and the following compounds HI2 were thermally vacuum deposited to a thickness of 100 ⁇ at a ratio of 98:2 (molar ratio) to form a hole injection layer.
  • a hole transport layer was formed by vacuum depositing a compound (1150 ⁇ ) represented by the following chemical formula HT1 on the hole injection layer.
  • an electron blocking layer was formed by vacuum depositing the compound of EB1 with a film thickness of 50 ⁇ on the hole transport layer.
  • Compound 1 synthesized in Preparation Example 1 and the compound represented by the formula BD below were vacuum deposited on the electron blocking layer to a film thickness of 200 ⁇ at a weight ratio of 25:1 to form a light emitting layer.
  • a hole blocking layer was formed by vacuum depositing the compound of HB1 with a film thickness of 50 ⁇ on the light emitting layer.
  • a compound represented by the formula ET1 and a compound represented by the formula LiQ were vacuum deposited on the hole blocking layer at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 310 ⁇ .
  • a cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 ⁇ and aluminum to a thickness of 1,000 ⁇ on the electron injection and transport layer.
  • LiF lithium fluoride
  • the deposition rate of organic matter was maintained at 0.4 ⁇ /sec to 0.7 ⁇ /sec, the deposition rate of lithium fluoride of the cathode was maintained at 0.3 ⁇ /sec, and aluminum was maintained at 2 ⁇ /sec, and the vacuum degree during deposition was 2x10.
  • An organic light emitting device was manufactured by maintaining -7 torr to 5x10 -6 torr.
  • An organic light emitting device was manufactured in the same manner as Example 1-1, except that the compounds listed in Table 1 below were used instead of Compound 1 in Example 1-1.
  • Example 1-1 An organic light emitting device was manufactured in the same manner as Example 1-1, except that the compounds listed in Table 1 below were used instead of Compound 1 in Example 1-1.
  • the compounds BH1 to BH8 used in Table 1 below are as follows.
  • T95 refers to the time it takes for the luminance to decrease from the initial luminance (1600 nit) to 95%.
  • the organic light-emitting device using the compound of the present invention as the light-emitting layer showed excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light-emitting device.
  • the organic light-emitting devices using the compounds of the present invention have lower voltage, It exhibited characteristics of high efficiency and long lifespan.

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Abstract

The present specification pertains to a compound of chemical formula 1 and an organic light-emitting element containing same.

Description

화합물 및 이를 포함하는 유기 발광 소자Compounds and organic light-emitting devices containing them
본 출원은 2022년 12월 2일에 한국특허청에 제출된 한국 특허 출원 제10-2022-0166812호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the filing date of Korean Patent Application No. 10-2022-0166812 filed with the Korea Intellectual Property Office on December 2, 2022, the entire contents of which are incorporated into this specification.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다. This specification relates to compounds and organic light-emitting devices containing the same.
일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 통상 양극과 음극 및 이 사이에 유기물층을 포함하는 구조를 가진다. 여기서 유기물층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며, 예컨대 정공주입층, 정공수송층, 발광층, 전자수송층, 전자주입층 등으로 이루어 질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이, 음극에서는 전자가 유기물층에 주입되게 되고, 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. In general, organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials. Organic light-emitting devices that utilize the organic light-emitting phenomenon usually have a structure including an anode, a cathode, and an organic material layer between them. Here, the organic material layer is often composed of a multi-layer structure made of different materials to increase the efficiency and stability of the organic light-emitting device, and may be composed of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In the structure of this organic light-emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic material layer. When the injected holes and electrons meet, an exciton is formed, and this exciton When it falls back to the ground state, it glows.
상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다.The development of new materials for organic light-emitting devices as described above continues to be required.
본 출원은 화합물 및 이를 포함하는 유기 발광 소자를 제공하고자 한다.The present application seeks to provide a compound and an organic light-emitting device containing the same.
본 명세서의 일 실시상태는 하기 화학식 1의 화합물을 제공한다:One embodiment of the present specification provides a compound of formula 1 below:
[화학식 1][Formula 1]
Figure PCTKR2023019646-appb-img-000001
Figure PCTKR2023019646-appb-img-000001
상기 화학식 1에 있어서, In Formula 1,
B는 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고, B is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
R1 내지 R16, R25 및 R26은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며, d는 0 내지 2의 정수이고,R1 to R16, R25 and R26 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and d is an integer of 0 to 2,
R21 내지 R24는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다. R21 to R24 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.
본 명세서의 또 하나의 실시상태는 애노드; 캐소드; 및 상기 애노드와 상기 캐소드 사이에 구비된 1층 이상의 유기물층을 포함하고, 상기 유기물층 중 1층 이상은 상기 화합물을 포함하는 것인 유기 발광 소자를 제공한다.Another embodiment of the present specification is an anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one layer of the organic material layer contains the compound.
본 발명의 일 실시상태에 따른 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있다.The compound according to an exemplary embodiment of the present invention can be used as a material for the organic layer of an organic light-emitting device.
본 발명의 구체적인 일 실시상태에 따른 화합물은 유기 발광 소자의 발광층 재료로 사용될 수 있다.The compound according to a specific embodiment of the present invention can be used as a material for the light-emitting layer of an organic light-emitting device.
본 발명의 일 실시상태에 따른 화합물은 유기 발광 소자에 포함되어 낮은 구동전압, 우수한 효율 특성, 또는 우수한 수명 특성을 갖게 하는 등 소자 특성을 향상시킬 수 있다.The compound according to an exemplary embodiment of the present invention can be included in an organic light emitting device to improve device characteristics such as low driving voltage, excellent efficiency characteristics, or excellent lifespan characteristics.
도 1 내지 도 3은 본 발명의 몇몇 실시상태에 따른 유기 발광 소자의 예를 도시한 것이다.1 to 3 show examples of organic light-emitting devices according to some embodiments of the present invention.
1: 기판1: substrate
2: 애노드2: anode
3: 발광층3: Light-emitting layer
4: 캐소드4: cathode
5: 정공주입층5: Hole injection layer
6: 정공수송층6: Hole transport layer
7: 발광층7: Light-emitting layer
8: 전자수송층8: Electron transport layer
9: 전자차단층9: Electronic blocking layer
10: 정공차단층10: Hole blocking layer
11: 전자 주입 및 수송층11: Electron injection and transport layer
이하 본 명세서에 대하여 더욱 상세히 설명한다. Hereinafter, this specification will be described in more detail.
본 명세서에 있어서, 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다.In this specification, when a part “includes” a certain component, this means that it may further include other components rather than excluding other components, unless specifically stated to the contrary.
본 명세서에 있어서, 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In this specification, when a member is said to be located “on” another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.
본 명세서에 있어서, 화합물의 중수소 치환율은 TLC-MS (Thin-Layer Chromatography/Mass Spectrometry)를 사용하여, 반응의 종결시점에서 분자량들이 이루는 분포의 max. 값을 기준으로 치환율을 계산하는 방법 또는 NMR을 이용한 정량분석 방법으로, Internal standard로 DMF를 첨가하고, 1H NMR 상의 integration 비율을 이용하여 총 peak의 적분량으로부터 D-치환율을 계산하는 방법을 통하여 파악할 수 있다.In this specification, the deuterium substitution rate of the compound is determined by using TLC-MS (Thin-Layer Chromatography/Mass Spectrometry), and is determined by maximizing the distribution of molecular weights at the end of the reaction. A method of calculating the substitution rate based on the value or a quantitative analysis method using NMR can be determined by adding DMF as an internal standard and calculating the D-substitution rate from the integral amount of the total peak using the integration rate on 1H NMR. You can.
본 발명에 있어서, "
Figure PCTKR2023019646-appb-img-000002
" 및 "*"는 각각 다른 치환기 또는 결합부에 연결되는 부위를 의미한다.In the present invention, "
Figure PCTKR2023019646-appb-img-000002
" and "*" each refer to a site connected to another substituent or bonding group.
상기 "치환" 이라는 용어는 화합물의 탄소 원자에 결합된 수소 원자가 다른 치환기로 바뀌는 것을 의미하며, 치환되는 위치는 수소 원자가 치환되는 위치 즉, 치환기가 치환 가능한 위치라면 한정하지 않으며, 2 이상 치환되는 경우, 2 이상의 치환기는 서로 동일하거나 상이할 수 있다.The term "substitution" means that a hydrogen atom bonded to a carbon atom of a compound is changed to another substituent. The position to be substituted is not limited as long as it is the position where the hydrogen atom is substituted, that is, a position where the substituent can be substituted, and if two or more substituents are substituted. , two or more substituents may be the same or different from each other.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기(-CN); 니트로기; 히드록시기; 알킬기; 시클로알킬기; 알콕시기; 포스핀옥사이드기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 알케닐기; 실릴기; 붕소기; 아민기; 아릴기; 및 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. 예컨대, "2 이상의 치환기가 연결된 치환기"는 바이페닐기일 수 있다. 즉, 바이페닐기는 아릴기일 수도 있고, 2개의 페닐기가 연결된 치환기로 해석될 수도 있다.As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Nitrile 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; 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. For example, “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.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 실릴기; 알콕시기; 아릴옥시기; 알킬기; 아릴기; 및 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다. As used herein, the term “substituted or unsubstituted” refers to deuterium; halogen group; Nitrile group; silyl group; Alkoxy group; Aryloxy group; Alkyl 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.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 알킬기; 아릴기; 및 헤테로고리기로 이루어진 군에서 선택된 1 또는 2 이상의 치환기로 치환되었거나 상기 예시된 치환기 중 2 이상의 치환기가 연결된 치환기로 치환되거나, 또는 어떠한 치환기도 갖지 않는 것을 의미한다.As used herein, the term “substituted or unsubstituted” refers to deuterium; Alkyl 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.
상기 치환기들의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Examples of the above substituents are described below, but are not limited thereto.
본 명세서에 있어서, 할로겐기의 예로는 불소(-F), 염소(-Cl), 브롬(-Br) 또는 요오드(-I)가 있다.In this specification, examples of halogen groups include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).
본 명세서에 있어서, 실릴기는 -SiYaYbYc의 화학식으로 표시될 수 있고, 상기 Ya, Yb 및 Yc는 각각 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기, t-부틸디메틸실릴기, 비닐디메틸실릴기, 프로필디메틸실릴기, 트리페닐실릴기, 디페닐실릴기, 페닐실릴기 등이 있으나 이에 한정되지 않는다. In the present specification, the silyl group may be represented by the formula -SiYaYbYc, where Ya, Yb, and Yc 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.
본 명세서에 있어서, 붕소기는 -BYdYe의 화학식으로 표시될 수 있고, 상기 Yd 및 Ye는 각각 수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기일 수 있다. 상기 붕소기는 구체적으로 디메틸붕소기, 디에틸붕소기, t-부틸디메틸붕소기, 디페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group may be represented by the chemical formula -BYdYe, where Yd and Ye 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, dimethyl boron group, diethyl boron group, t-butyldimethyl boron group, diphenyl boron group, and phenyl boron group.
본 명세서에 있어서, 알킬기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나 1 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 30이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알킬기의 탄소수는 1 내지 10이다. 알킬기의 구체적인 예로는 메틸기, 에틸기, 프로필기, n-프로필기, 이소프로필기, 부틸기, n-부틸기, 이소부틸기, tert-부틸기, 펜틸기, n-펜틸기, 헥실기, n-헥실기, 헵틸기, n-헵틸기, 옥틸기, n-옥틸기 등이 있으나, 이들에 한정되지 않는다.In the present specification, the alkyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 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. Specific examples of 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.
본 명세서에 있어서, 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 20인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, i-프로필옥시, n-부톡시, 이소부톡시, tert-부톡시, sec-부톡시, n-펜틸옥시, 네오펜틸옥시, 이소펜틸옥시, n-헥실옥시, 3,3-디메틸부틸옥시, 2-에틸부틸옥시, n-옥틸옥시, n-노닐옥시, n-데실옥시 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the alkoxy group may be straight chain, branched chain, or ring chain. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, It may be isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but is not limited thereto. .
본 명세서에 기재된 알킬기, 알콕시기 및 그 외 알킬기 부분을 포함하는 치환체는 직쇄 또는 분쇄 형태를 모두 포함한다.Substituents containing alkyl groups, alkoxy groups, and other alkyl group moieties described in this specification include both straight-chain or branched forms.
본 명세서에 있어서, 알케닐기는 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐, 1-프로페닐, 이소프로페닐, 1-부테닐, 2-부테닐, 3-부테닐, 1-펜테닐, 2-펜테닐, 3-펜테닐, 3-메틸-1-부테닐, 1,3-부타디에닐, 알릴, 1-페닐비닐-1-일, 2-페닐비닐-1-일, 2,2-디페닐비닐-1-일, 2-페닐-2-(나프틸-1-일)비닐-1-일, 2,2-비스(디페닐-1-일)비닐-1-일, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present specification, the alkenyl group may be straight chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 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, stilbenyl group, styrenyl group, etc., but are not limited to these.
본 명세서에 있어서, 시클로알킬기는 특별히 한정되지 않으나, 탄소수 3 내지 60인 것이 바람직하며, 일 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면, 상기 시클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 시클로프로필기, 시클로부틸기, 시클로펜틸기, 시클로헥실기, 시클로헵틸기, 시클로옥틸기 등이 있으나, 이에 한정되지 않는다. In the present specification, 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.
본 명세서에 있어서, 아민기는 -NH2이며, 상기 아민기에는 전술한 알킬기, 아릴기, 헤테로고리기, 알케닐기, 시클로알킬기 및 이들의 조합 등이 치환될 수 있다. 상기 치환된 아민기의 탄소수는 특별히 한정되지 않으나, 1 내지 30인 것이 바람직하다. 일 실시상태에 따르면, 상기 아민기의 탄소수는 1 내지 20이다. 일 실시상태에 따르면, 상기 아민기의 탄소수는 1 내지 10이다. 치환된 아민기의 구체적인 예로는 메틸아민기, 디메틸아민기, 에틸아민기, 디에틸아민기, 페닐아민기, 9,9-디메틸플루오레닐페닐아민기, 피리딜페닐아민기, 디페닐아민기, 페닐피리딜아민기, 나프틸아민기, 바이페닐아민기, 안트라세닐아민기, 디벤조퓨라닐페닐아민기, 9-메틸안트라세닐아민기, 디페닐아민기, 페닐나프틸아민기, 디톨릴아민기, 페닐톨릴아민기, 디페닐아민기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, the amine group is -NH 2 , and 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. Specific examples of substituted amine groups include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, and diphenylamine. 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.
본 명세서에 있어서, 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며, 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면, 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기, 바이페닐기, 터페닐기, 쿼터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 크라이세닐기, 플루오레닐기, 트리페닐레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, 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 such as a phenyl group, biphenyl group, terphenyl group, or quarterphenyl group, but is not limited thereto. 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.
본 명세서에 있어서, 플루오레닐기는 치환될 수 있고, 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다.In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure.
상기 플루오레닐기가 치환되는 경우,
Figure PCTKR2023019646-appb-img-000003
,
Figure PCTKR2023019646-appb-img-000004
등의 스피로플루오레닐기,
Figure PCTKR2023019646-appb-img-000005
(9,9-디메틸플루오레닐기), 및
Figure PCTKR2023019646-appb-img-000006
(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,
Figure PCTKR2023019646-appb-img-000003
,
Figure PCTKR2023019646-appb-img-000004
Spirofluorenyl groups such as
Figure PCTKR2023019646-appb-img-000005
(9,9-dimethylfluorenyl group), and
Figure PCTKR2023019646-appb-img-000006
It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited to this.
본 명세서에 있어서, 아릴옥시기 중의 아릴기는 전술한 아릴기에 관한 설명이 적용될 수 있다.In the present specification, the above-described description of the aryl group may be applied to the aryl group in the aryloxy group.
본 명세서에 있어서, 헤테로고리기는 이종원자로 N, O, P, S, Si 및 Se 중 1개 이상을 포함하는 고리기로서, 탄소수는 특별히 한정되지 않으나 탄소수 2 내지 60인 것이 바람직하다. 일 실시상태에 따르면, 상기 헤테로고리기의 탄소수는 2 내지 30이다. 일 실시상태에 따르면, 상기 헤테로고리기의 탄소수는 2 내지 20이다. 헤테로고리기의 예로는 피리딘기, 피롤기, 피리미딘기, 퀴놀린기, 피리다지닐기, 퓨란기, 티오펜기, 이미다졸기, 피라졸기, 디벤조퓨란기, 디벤조티오펜기, 카바졸기, 벤조카바졸기, 나프토벤조퓨란기, 벤조나프토티오펜기, 인데노카바졸기, 트리아지닐기 등이 있으나, 이들에만 한정되는 것은 아니다.In the present specification, 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. Examples of 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.
본 명세서에 있어서, 헤테로아릴기는 방향족인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In the present specification, the description regarding the heterocyclic group described above can be applied, except that the heteroaryl group is aromatic.
본 명세서에 있어서, 상기 아릴렌기는 2가인 것을 제외하고는 상기 아릴기에 대한 설명이 적용될 수 있다.In the present specification, the description of the aryl group may be applied, except that the arylene group is divalent.
본 명세서에 있어서, 인접한 기와 서로 결합하여 형성되는 치환 또는 비치환된 고리에서, "고리"는 탄화수소고리; 또는 헤테로고리를 의미한다.In the present specification, in a substituted or unsubstituted ring formed by combining adjacent groups, “ring” is a hydrocarbon ring; Or refers to a heterocycle.
상기 탄화수소고리는 방향족, 지방족, 또는 방향족과 지방족의 축합고리일 수 있으며, 상기 시클로알킬기 또는 아릴기의 예시 중에서 선택될 수 있다.The hydrocarbon ring may be an aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group.
본 명세서에 있어서, 인접하는 기와 서로 결합하여 고리를 형성한다는 의미는 인접하는 기와 서로 결합하여 치환 또는 비치환된 지방족 탄화수소고리; 치환 또는 비치환된 방향족 탄화수소고리; 치환 또는 비치환된 지방족 헤테로고리; 치환 또는 비치환된 방향족 헤테로고리; 또는 이들의 축합고리를 형성하는 것을 의미한다. 상기 탄화수소고리는 탄소와 수소 원자로만 이루어진 고리를 의미한다. 상기 헤테로고리는 N, O, P, S, Si 및 Se 중에서 선택된 1 이상의 헤테로원자를 포함하는 고리를 의미한다. 본 명세서에 있어서, 상기 지방족 탄화수소고리, 방향족 탄화수소고리, 지방족 헤테로고리 및 방향족 헤테로고리는 단환 또는 다환일 수 있다.In the present specification, 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 heteroatoms selected from N, O, P, S, Si, and Se. In the present specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle, and aromatic heterocycle may be monocyclic or polycyclic.
본 명세서에 있어서, 지방족 탄화수소고리란 방향족이 아닌 고리로서 탄소와 수소 원자로만 이루어진 고리를 의미한다. 지방족 탄화수소고리의 예로는 시클로프로판, 시클로부탄, 시클로부텐, 시클로펜탄, 시클로펜텐, 시클로헥산, 시클로헥센, 1,4-시클로헥사디엔, 시클로헵탄, 시클로헵텐, 시클로옥탄, 시클로옥텐 등이 있으나, 이에 한정되지 않는다.In the present specification, 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.
본 명세서에 있어서, 방향족 탄화수소고리란 탄소와 수소 원자로만 이루어진 방향족의 고리를 의미한다. 방향족 탄화수소고리의 예로는 벤젠, 나프탈렌, 안트라센, 페난트렌, 페릴렌, 플루오란텐, 트리페닐렌, 페날렌, 파이렌, 테트라센, 크라이센, 펜타센, 플루오렌, 인덴, 아세나프틸렌, 벤조플루오렌, 스피로플루오렌 등이 있으나, 이에 한정되지 않는다. 본 명세서에 있어서, 방향족 탄화수소고리는 아릴기와 동일한 의미로 해석될 수 있다.In this specification, an aromatic hydrocarbon ring refers to an aromatic ring consisting only of carbon and hydrogen atoms. Examples of 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. In the present specification, an aromatic hydrocarbon ring can be interpreted to have the same meaning as an aryl group.
본 명세서에 있어서, 지방족 헤테로고리란 헤테로원자 중 1개 이상을 포함하는 지방족 고리를 의미한다. 지방족 헤테로고리의 예로는, 옥시레인(oxirane), 테트라하이드로퓨란, 1,4-디옥세인(1,4-dioxane), 피롤리딘, 피페리딘, 모르폴린(morpholine), 옥세판, 아조케인, 티오케인 등이 있으나, 이에 한정되지 않는다.As used herein, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, and azocaine. , thiocane, etc., but is not limited thereto.
본 명세서에 있어서, 방향족 헤테로고리란 헤테로원자 중 1개 이상을 포함하는 방향족 고리를 의미한다. 방향족 헤테로고리의 예로는, 피리딘, 피롤, 피리미딘, 피리다진, 퓨란, 티오펜, 이미다졸, 파라졸, 옥사졸, 이소옥사졸, 티아졸, 이소티아졸, 트리아졸, 옥사디아졸, 티아디아졸, 디티아졸, 테트라졸, 피란, 티오피란, 디아진, 옥사진, 티아진, 다이옥신, 트리아진, 테트라진, 이소퀴놀린, 퀴놀린, 퀴논, 퀴나졸린, 퀴녹살린, 나프티리딘, 아크리딘, 페난트리딘, 디아자나프탈렌, 드리아자인덴, 인돌, 인돌리진, 벤조티아졸, 벤조옥사졸, 벤조이미다졸, 벤조티오펜, 벤조퓨란, 디벤조티오펜, 디벤조퓨란, 카바졸, 벤조카바졸, 디벤조카바졸, 페나진, 이미다조피리딘, 페녹사진, 인돌로카바졸, 인데노카바졸 등이 있으나, 이에 한정되지 않는다.As used herein, an aromatic heterocycle refers to an aromatic ring containing one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, and thiazole. Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine , phenanthridine, diazanaphthalene, driazindene, indole, indolizine, benzothiazole, benzoxazole, benzoimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzoyl Examples include, but are not limited to, carbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, indolocarbazole, and indenocarbazole.
이하 본 발명의 바람직한 실시상태를 상세히 설명한다. 그러나 본 발명의 실시상태는 여러 가지 형태로 변형될 수 있으며, 본 발명의 범위가 아래에서 설명하는 실시상태들에 한정되지는 않는다.Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiments of the present invention may be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.
본 명세서의 일 실시상태에 따른 화합물은 전술한 바와 같이 화학식 1로 표시된다. 상기 화학식 1의 화합물은 안트라센의 9 및 10번 탄소에 각각 디벤조퓨란으로 치환된 바이페닐기와 B가 치환된 것을 특징으로 하며, 여기서 디벤조퓨란은 바이페닐의 오르토 위치에 결합하는 것을 특징으로 한다. 이와 같은 구성적 특징에 의하여 상기 화합물을 유기 발광 소자에 적용하는 경우 저전압, 고효율 및/또는 장수명 효과를 나타낼 수 있다.The compound according to an exemplary embodiment of the present specification is represented by Formula 1 as described above. The compound of Formula 1 is characterized in that a biphenyl group substituted with dibenzofuran and B are substituted at carbons 9 and 10 of anthracene, respectively, where dibenzofuran is characterized in that it is bonded to the ortho position of biphenyl. . Due to these structural characteristics, when the compound is applied to an organic light emitting device, it can exhibit low voltage, high efficiency, and/or long life effects.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1은 하기 화학식 21 내지 23 중 어느 하나로 표시될 수 있다. According to an exemplary embodiment of the present specification, Formula 1 may be represented by any one of the following Formulas 21 to 23.
[화학식 21][Formula 21]
Figure PCTKR2023019646-appb-img-000007
Figure PCTKR2023019646-appb-img-000007
[화학식 22][Formula 22]
Figure PCTKR2023019646-appb-img-000008
Figure PCTKR2023019646-appb-img-000008
[화학식 23][Formula 23]
Figure PCTKR2023019646-appb-img-000009
Figure PCTKR2023019646-appb-img-000009
상기 화학식 21 내지 23에 있어서, 치환기 설명은 상기 화학식 1에서 정의한 바와 같다. In Formulas 21 to 23, descriptions of substituents are as defined in Formula 1 above.
본 명세서의 일 실시상태에 따르면, 상기 R21 내지 R26은 수소; 또는 중수소이다.According to an exemplary embodiment of the present specification, R21 to R26 are hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 B는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 하기 화학식 11의 기이다. According to an exemplary embodiment of the present specification, B is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it is a group of the following formula (11).
[화학식 11][Formula 11]
Figure PCTKR2023019646-appb-img-000010
Figure PCTKR2023019646-appb-img-000010
상기 화학식 11에 있어서, In Formula 11,
X는 O 또는 S이고, X is O or S,
R17은 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며, R17 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
a 및 b는 각각 0 또는 1이며, c는 0 내지 12의 정수이고,a and b are each 0 or 1, c is an integer from 0 to 12,
*은 화학식 1에 결합되는 부위이다. * is the site bound to Chemical Formula 1.
본 명세서의 일 실시상태에 따르면, 상기 B는 치환 또는 비치환된 페닐기; 치환 또는 비치환된 비페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 트리페닐레닐기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 디벤조티오펜기; 치환 또는 비치환된 나프토벤조퓨란기; 또는 치환 또는 비치환된 나프토벤조티오펜기이다. According to an exemplary embodiment of the present specification, B is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted naphthobenzofuran group; Or a substituted or unsubstituted naphthobenzothiophene group.
본 명세서의 일 실시상태에 따르면, 상기 B는 중수소 치환율이 0%이다. According to an exemplary embodiment of the present specification, B has a deuterium substitution rate of 0%.
본 명세서의 일 실시상태에 따르면, 상기 B는 중수소 치환율이 10% 내지 100%이다. According to an exemplary embodiment of the present specification, B has a deuterium substitution rate of 10% to 100%.
본 명세서의 일 실시상태에 따르면, 상기 B는 중수소 치환율이 20% 내지 100%이다. According to an exemplary embodiment of the present specification, B has a deuterium substitution rate of 20% to 100%.
본 명세서의 일 실시상태에 따르면, 상기 B는 중수소 치환율이 50% 내지 100%이다. According to an exemplary embodiment of the present specification, B has a deuterium substitution rate of 50% to 100%.
본 명세서의 일 실시상태에 따르면, 상기 B는 하기 구조 중 어느 하나 또는 둘 이상이 연결된 구조이고, 하기 구조는 중수소로 치환 또는 비치환된다.According to an exemplary embodiment of the present specification, B is a structure in which one or more of the following structures are connected, and the following structures are substituted or unsubstituted with deuterium.
Figure PCTKR2023019646-appb-img-000011
Figure PCTKR2023019646-appb-img-000011
Figure PCTKR2023019646-appb-img-000012
Figure PCTKR2023019646-appb-img-000012
상기 구조에 있어서,
Figure PCTKR2023019646-appb-img-000013
는 상기 화학식 1에 결합되는 부분이다.In the above structure,
Figure PCTKR2023019646-appb-img-000013
is a portion bound to Formula 1 above.
본 명세서의 일 실시상태에 따르면, 상기 R1 내지 R16은 각각 수소; 또는 중수소이다. According to an exemplary embodiment of the present specification, R1 to R16 are each hydrogen; Or deuterium.
본 명세서의 일 실시상태에 따르면, 상기 R1 내지 R8은 수소이다.According to an exemplary embodiment of the present specification, R1 to R8 are hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 R1 내지 R8은 중수소이다.According to an exemplary embodiment of the present specification, R1 to R8 are deuterium.
본 명세서의 일 실시상태에 따르면, 상기 R9 내지 R16은 수소이다. According to an exemplary embodiment of the present specification, R9 to R16 are hydrogen.
본 명세서의 일 실시상태에 따르면, 상기 R9 내지 R16은 중수소이다. According to an exemplary embodiment of the present specification, R9 to R16 are deuterium.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 화합물의 중수소 치환율은 0%이다. According to an exemplary embodiment of the present specification, the deuterium substitution rate of the compound of Formula 1 is 0%.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 화합물의 중수소 치환율은 10% 내지 100%이다. According to an exemplary embodiment of the present specification, the deuterium substitution rate of the compound of Formula 1 is 10% to 100%.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 화합물의 중수소 치환율은 20% 내지 100%이다. According to an exemplary embodiment of the present specification, the deuterium substitution rate of the compound of Formula 1 is 20% to 100%.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 화합물의 중수소 치환율은 50% 내지 100%이다. According to an exemplary embodiment of the present specification, the deuterium substitution rate of the compound of Formula 1 is 50% to 100%.
본 명세서의 일 실시상태에 따르면, 상기 화합물은 하기 구조들 중에서 선택되는 어느 하나이다.According to an exemplary embodiment of the present specification, the compound is any one selected from the following structures.
Figure PCTKR2023019646-appb-img-000014
Figure PCTKR2023019646-appb-img-000014
Figure PCTKR2023019646-appb-img-000015
Figure PCTKR2023019646-appb-img-000015
Figure PCTKR2023019646-appb-img-000016
Figure PCTKR2023019646-appb-img-000016
Figure PCTKR2023019646-appb-img-000017
Figure PCTKR2023019646-appb-img-000017
Figure PCTKR2023019646-appb-img-000018
Figure PCTKR2023019646-appb-img-000018
Figure PCTKR2023019646-appb-img-000019
Figure PCTKR2023019646-appb-img-000019
Figure PCTKR2023019646-appb-img-000020
Figure PCTKR2023019646-appb-img-000020
Figure PCTKR2023019646-appb-img-000021
Figure PCTKR2023019646-appb-img-000021
Figure PCTKR2023019646-appb-img-000022
Figure PCTKR2023019646-appb-img-000022
Figure PCTKR2023019646-appb-img-000023
Figure PCTKR2023019646-appb-img-000023
Figure PCTKR2023019646-appb-img-000024
Figure PCTKR2023019646-appb-img-000024
Figure PCTKR2023019646-appb-img-000025
Figure PCTKR2023019646-appb-img-000025
Figure PCTKR2023019646-appb-img-000026
Figure PCTKR2023019646-appb-img-000026
본 명세서의 일 실시상태는 애노드; 캐소드; 및 상기 애노드와 상기 캐소드 사이에 구비된 1층 이상의 유기물층을 포함하고, 상기 유기물층 중 1층 이상은 상기 화합물을 포함하는 것인 유기 발광 소자를 제공한다.An exemplary embodiment of the present specification includes an anode; cathode; and at least one organic material layer provided between the anode and the cathode, wherein at least one layer of the organic material layer contains the compound.
구체적으로, 상기 유기 발광 소자는 애노드; 캐소드; 및 상기 애노드와 상기 캐소드 사이에 구비된 발광층을 포함하는 1층 이상의 유기물층을 포함하고, 상기 유기물층 중 1층 이상은 상기 화학식 1의 화합물을 포함한다.Specifically, the organic light emitting device includes an anode; cathode; and at least one organic material layer including a light-emitting layer provided between the anode and the cathode, and at least one layer of the organic material layer includes the compound of Formula 1.
본 명세서의 유기 발광 소자는 전술한 화합물을 이용하여 한 층 이상의 유기물층을 형성하는 것을 제외하고는, 통상의 유기 발광 소자의 제조방법 및 재료에 의하여 제조될 수 있다.The organic light emitting device of the present specification can be manufactured using conventional organic light emitting device manufacturing methods and materials, except that one or more organic material layers are formed using the above-described compounds.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 화합물을 포함하는 유기물층의 두께는 10 Å 내지 600 Å이고, 바람직하게는 50 Å 내지 500 Å이고, 더욱 바람직하게는 200 Å 내지 400 Å이다.According to an exemplary embodiment of the present specification, the thickness of the organic material layer containing the compound of Formula 1 is 10 Å to 600 Å, preferably 50 Å to 500 Å, and more preferably 200 Å to 400 Å.
상기 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥 코팅, 잉크젯 프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.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. Here, the solution application method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
예컨대, 본 명세서의 유기 발광 소자는 기판 상에 애노드, 유기물층 및 캐소드를 순차적으로 적층시킴으로써 제조할 수 있다. 이 때 스퍼터링법(sputtering)이나 전자빔 증발법(e-beam evaporation)과 같은 물리 증착 방법(PVD: physical Vapor Deposition)을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 애노드를 형성하고, 그 위에 정공주입층, 정공수송층, 전자차단층, 발광층 및 전자수송층을 포함하는 유기물층을 형성한 후, 그 위에 캐소드로 사용할 수 있는 물질을 증착시킴으로써 제조될 수 있다. 이와 같은 방법 외에도, 기판 상에 캐소드 물질부터 유기물층, 애노드 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. 또한, 상기 화학식 1의 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물층으로 형성될 수 있다. 여기서, 용액 도포법이라 함은 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯프린팅, 스크린 프린팅, 스프레이법, 롤 코팅 등을 의미하지만, 이들만으로 한정되는 것은 아니다.For example, the organic light emitting device of the present specification can be manufactured by sequentially stacking an anode, an organic material layer, and a cathode on a substrate. At this time, a metal or a conductive metal oxide or an alloy thereof is deposited on the substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation. It can be manufactured by forming an anode, forming an organic material layer including a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can be made by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. Additionally, 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. Here, the solution application method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 단층 구조로 이루어질 수 있으며, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수도 있다. 상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 예컨대, 상기 유기물층은 정공주입층, 정공수송층, 정공 주입 및 수송층, 전자차단층, 발광층, 전자수송층, 전자주입층, 및 전자 주입 및 수송층 등을 포함하는 다층 구조일 수 있다. 그러나, 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수 또는 더 많은 수의 유기물층을 포함할 수 있다.According to an exemplary embodiment of the present specification, the organic material layer may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. When the organic light emitting device includes a plurality of organic material layers, for example, the organic material layer includes 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, and an electron injection and transport layer. It may be a multi-layered structure including: However, the structure of the organic light emitting device is not limited to this and may include fewer or more organic material layers.
상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. 또한, 상기 유기물층은 다양한 고분자 소재를 사용하여 증착법이 아닌 용매 공정(solvent process), 예컨대 스핀 코팅, 딥 코팅, 닥터 블레이딩, 스크린 프린팅, 잉크젯 프린팅 또는 열 전사법 등의 방법에 의하여 더 적은 수의 층으로 제조할 수 있다.The organic material layer may be formed of the same material or a different material. In addition, 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.
본 명세서의 일 실시상태에 따르면, 상기 화학식 1의 화합물을 포함하는 유기물층은 발광층일 수 있다. According to an exemplary embodiment of the present specification, the organic material layer containing the compound of Formula 1 may be a light-emitting layer.
상기 화학식 1의 화합물을 포함하는 발광층은 단독 물질만을 포함할 수도 있으나, 추가의 물질을 더 포함할 수 있다. 예컨대, 상기 화학식 1의 화합물은 발광층에서 호스트로서 역할을 할 수 있으며, 이 경우 추가의 도펀트를 더 포함할 수 있다. The light-emitting layer containing the compound of Formula 1 may include only a single material, but may also include additional materials. For example, the compound of Formula 1 may serve as a host in the light-emitting layer, and in this case, it may further include an additional dopant.
본 명세서의 일 실시상태에 따르면, 상기 발광층은 형광 도펀트 또는 인광 도펀트를 더 포함한다. According to an exemplary embodiment of the present specification, the light-emitting layer further includes a fluorescent dopant or a phosphorescent dopant.
이때, 상기 도펀트로는 (4,6-F2ppy)2Irpic와 같은 인광 물질이나, spiro-DPVBi, spiro-6P, 디스틸벤젠(DSB), 디스트릴아릴렌(DSA), PFO계 고분자, PPV계 고분자, 안트라센계 화합물, 파이렌계 화합물, 보론계 화합물 등과 같은 형광 물질이 사용될 수 있으나, 이에 한정되는 것은 아니다.At this time, the dopant is a phosphorescent material such as (4,6-F 2 ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distrylarylene (DSA), PFO-based polymer, Fluorescent materials such as PPV-based polymers, anthracene-based compounds, pyrene-based compounds, boron-based compounds, etc. may be used, but are not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 발광층 내의 도펀트는 호스트 100 중량부 대비 1 중량부 내지 50 중량부로 포함된다.According to an exemplary embodiment of the present specification, 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.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 정공차단층, 전자수송층 또는 전자주입층을 포함한다. 이때, 상기 정공차단층, 전자수송층 또는 전자주입층은 상기 화합물을 포함하거나, 포함하지 않을 수 있다.According to an exemplary embodiment of the present specification, the organic material layer includes a hole blocking layer, an electron transport layer, or an electron injection layer. At this time, the hole blocking layer, electron transport layer, or electron injection layer may or may not include the compound.
본 명세서의 일 실시상태에 따르면, 상기 유기물층은 정공주입층, 정공수송층 또는 전자차단층을 포함한다. 이때, 상기 정공주입층, 정공수송층 또는 전자차단층은 상기 화합물을 포함하거나, 포함하지 않을 수 있다.According to an exemplary embodiment of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or an electron blocking layer. At this time, the hole injection layer, hole transport layer, or electron blocking layer may or may not include the compound.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 애노드; 캐소드; 및 애노드와 캐소드 사이에 구비된 발광층을 포함하고, 상기 발광층과 애노드 사이에 단층의 유기물층을 더 포함하며, 상기 발광층이 상기 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic light emitting device includes an anode; cathode; and a light-emitting layer provided between the anode and the cathode, and further comprising a single-layer organic material layer between the light-emitting layer and the anode, wherein the light-emitting layer includes the compound.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 애노드; 캐소드; 및 애노드와 캐소드 사이에 구비된 발광층을 포함하고, 상기 발광층과 애노드 사이에 다층의 유기물층을 더 포함하며, 상기 발광층이 상기 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic light emitting device includes an anode; cathode; and a light-emitting layer provided between the anode and the cathode, and further comprising a multi-layer organic material layer between the light-emitting layer and the anode, wherein the light-emitting layer includes the compound.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 애노드; 캐소드; 및 애노드와 캐소드 사이에 구비된 발광층을 포함하고, 상기 발광층과 애노드 사이에 정공주입층, 정공수송층 및 전자차단층 중 1층 이상을 더 포함하며, 상기 발광층이 상기 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic light emitting device includes an anode; cathode; and a light-emitting layer provided between the anode and the cathode, and further comprising at least one of a hole injection layer, a hole transport layer, and an electron blocking layer between the light-emitting layer and the anode, and the light-emitting layer includes the compound.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 애노드; 캐소드; 및 애노드와 캐소드 사이에 구비된 발광층을 포함하고, 상기 애노드와 발광층 사이에 정공주입층, 정공수송층 및 전자차단층을 포함하며, 상기 발광층이 상기 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic light emitting device includes an anode; cathode; and a light-emitting layer provided between the anode and the cathode, and a hole injection layer, a hole transport layer, and an electron blocking layer between the anode and the light-emitting layer, and the light-emitting layer includes the compound.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 애노드; 정공주입층; 정공수송층; 전자차단층; 발광층; 및 캐소드가 순차적으로 구비된 구조이며, 상기 발광층이 상기 화합물을 포함한다. 이때, 상기 각 층들 사이에는 추가의 유기물층이 더 구비될 수 있다.According to an exemplary embodiment of the present specification, the organic light emitting device includes an anode; hole injection layer; Hole transport layer; Electronic blocking layer; light emitting layer; and a cathode are sequentially provided, and the light-emitting layer includes the compound. At this time, an additional organic material layer may be further provided between each of the layers.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 애노드; 캐소드; 및 애노드와 캐소드 사이에 구비된 발광층을 포함하고, 상기 발광층과 캐소드 사이에 단층의 유기물층을 더 포함하며, 상기 발광층이 상기 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic light emitting device includes an anode; cathode; and a light-emitting layer provided between the anode and the cathode, and further comprising a single-layer organic material layer between the light-emitting layer and the cathode, wherein the light-emitting layer includes the compound.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 애노드; 캐소드; 및 애노드와 캐소드 사이에 구비된 발광층을 포함하고, 상기 발광층과 캐소드 사이에 다층의 유기물층을 더 포함하며, 상기 발광층이 상기 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic light emitting device includes an anode; cathode; and a light-emitting layer provided between the anode and the cathode, and further comprising a multi-layer organic material layer between the light-emitting layer and the cathode, wherein the light-emitting layer includes the compound.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 애노드; 캐소드; 및 애노드와 캐소드 사이에 구비된 발광층을 포함하고, 상기 캐소드와 발광층 사이에 정공차단층, 전자주입층, 전자수송층, 및 전자 주입 및 수송층 중 1층 이상을 더 포함하며, 상기 발광층이 상기 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic light emitting device includes an anode; cathode; and a light-emitting layer provided between the anode and the cathode, further comprising one or more layers of a hole blocking layer, an electron injection layer, an electron transport layer, and an electron injection and transport layer between the cathode and the light-emitting layer, wherein the light-emitting layer contains the compound. Includes.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 애노드; 캐소드; 및 애노드와 캐소드 사이에 구비된 발광층을 포함하고, 상기 캐소드와 발광층 사이에 정공차단층, 및 전자 주입 및 수송층을 포함하며, 상기 발광층이 상기 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic light emitting device includes an anode; cathode; and a light-emitting layer provided between the anode and the cathode, and a hole blocking layer and an electron injection and transport layer between the cathode and the light-emitting layer, and the light-emitting layer includes the compound.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 애노드; 발광층; 정공차단층; 전자 주입 및 수송층; 및 캐소드가 순차적으로 구비된 구조이며, 상기 발광층이 상기 화합물을 포함한다. 이때, 상기 각 층들 사이에는 추가의 유기물층이 더 구비될 수 있다.According to an exemplary embodiment of the present specification, the organic light emitting device includes an anode; light emitting layer; hole blocking layer; electron injection and transport layer; and a cathode are sequentially provided, and the light-emitting layer includes the compound. At this time, an additional organic material layer may be further provided between each of the layers.
본 명세서의 일 실시상태에 따르면, 상기 유기 발광 소자는 애노드; 정공주입층; 정공수송층; 전자차단층; 발광층; 정공차단층; 전자주입 및 수송층; 및 캐소드가 순차적으로 적층된 구조이고, 상기 발광층이 상기 화합물을 포함한다.According to an exemplary embodiment of the present specification, the organic light emitting device includes an anode; hole injection layer; Hole transport layer; Electronic blocking layer; light emitting layer; hole blocking layer; electron injection and transport layer; and a cathode are sequentially stacked, and the light-emitting layer includes the compound.
예컨대, 본 명세서의 유기 발광 소자의 구조는 도 1 내지 도 3에 나타난 것과 같은 구조를 가질 수 있으나 이에만 한정되는 것은 아니다.For example, the structure of the organic light emitting device of the present specification may have the same structure as shown in FIGS. 1 to 3, but is not limited thereto.
도 1은 기판(1), 애노드(2), 발광층(3) 및 캐소드(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다.Figure 1 shows an example of an organic light emitting device consisting of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
도 2는 기판(1), 애노드(2), 정공주입층(5), 정공수송층(6), 발광층(7), 전자수송층(8) 및 캐소드(4)로 이루어진 유기 발광 소자의 예를 도시한 것이다.Figure 2 shows an example of an organic light emitting device consisting of a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), light emitting layer (7), electron transport layer (8), and cathode (4). It was done.
도 3은 기판(1), 애노드(2), 정공주입층(5), 정공수송층(6), 전자차단층(9), 발광층(7), 정공차단층(10), 전자 주입 및 수송층(11) 및 캐소드(4)로 이어진 유기 발광 소자의 예를 도시한 것이다.Figure 3 shows a substrate (1), anode (2), hole injection layer (5), hole transport layer (6), electron blocking layer (9), light emitting layer (7), hole blocking layer (10), electron injection and transport layer ( 11) and an example of an organic light emitting device connected to a cathode 4 are shown.
구체적으로, 상기 유기 발광 소자는 상기 도면에 명시된 구조 외에 예컨대 하기와 같은 적층 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.Specifically, the organic light emitting device may have a stacked structure, for example, as shown below, in addition to the structure specified in the drawings, but is not limited thereto.
(1) 애노드/정공수송층/발광층/캐소드(1) Anode/hole transport layer/light emitting layer/cathode
(2) 애노드/정공주입층/정공수송층/발광층/캐소드(2) Anode/hole injection layer/hole transport layer/light emitting layer/cathode
(3) 애노드/정공수송층/발광층/전자수송층/캐소드(3) Anode/hole transport layer/light emitting layer/electron transport layer/cathode
(4) 애노드/정공수송층/발광층/전자수송층/전자주입층/캐소드(4) Anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(5) 애노드/정공주입층/정공수송층/발광층/전자수송층/캐소드(5) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/cathode
(6) 애노드/정공주입층/정공수송층/발광층/전자수송층/전자주입층/캐소드(6) Anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(7) 애노드/정공수송층/전자차단층/발광층/전자수송층/캐소드(7) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(8) 애노드/정공수송층/전자차단층/발광층/전자수송층/전자주입층/캐소드(8) Anode/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/electron injection layer/cathode
(9) 애노드/정공주입층/정공수송층/전자차단층/발광층/전자수송층/캐소드(9) Anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/electron transport layer/cathode
(10) 애노드/정공주입층/정공수송층/전자차단층/발광층/전자수송층/전자주입층/캐소드(10) Anode/hole injection layer/hole transport layer/electron blocking layer/light-emitting layer/electron transport layer/electron injection layer/cathode
(11) 애노드/정공수송층/발광층/정공차단층/전자수송층/캐소드(11) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode
(12) 애노드/정공수송층/발광층/ 정공차단층/전자수송층/전자주입층/캐소드(12) Anode/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode
(13) 애노드/정공주입층/정공수송층/발광층/정공차단층/전자수송층/캐소드(13) Anode/hole injection layer/hole transport layer/light emitting layer/hole blocking layer/electron transport layer/cathode
(14) 애노드/정공주입층/정공수송층/발광층/정공차단층/전자수송층/전자주입층/캐소드(14) Anode/hole injection layer/hole transport layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode
(15) 애노드/정공주입층/정공수송층/전자차단층/발광층/정공차단층/전자수송층/전자주입층/캐소드(15) Anode/hole injection layer/hole transport layer/electron blocking layer/light-emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode
본 명세서의 일 실시상태에 따르면, 상기 '전자수송층/전자주입층'은 '전자 주입 및 수송층' 또는 '전자 주입과 전자 수송을 동시에 하는 층'으로 대체될 수 있다. 예컨대, 상기 (15)는 '애노드/정공주입층/정공수송층/전자차단층/발광층/정공차단층/전자 주입 및 수송층/캐소드'의 적층 순서를 가지는 유기 발광 소자일 수 있다.According to an exemplary embodiment of the present specification, the ‘electron transport layer/electron injection layer’ may be replaced with an ‘electron injection and transport layer’ or a ‘layer that performs electron injection and electron transport simultaneously’. For example, (15) may be an organic light emitting device having a stacking order of 'anode/hole injection layer/hole transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron injection and transport layer/cathode'.
본 명세서의 일 실시상태에 따르면, 상기 '정공주입층/정공수송층'은 '정공 주입 및 수송층' 또는 '정공 주입과 정공 수송을 동시에 하는 층'으로 대체될 수 있다. 예컨대, 상기 (15)는 '애노드/정공 주입 및 수송층/전자차단층/발광층/정공차단층/전자수송층/전자주입층/캐소드'의 적층 순서를 가지는 유기 발광 소자일 수 있다.According to an exemplary embodiment of the present specification, the 'hole injection layer/hole transport layer' may be replaced with a 'hole injection and transport layer' or a 'layer that performs hole injection and hole transport at the same time'. For example, (15) may be an organic light emitting device having a stacking order of 'anode/hole injection and transport layer/electron blocking layer/light emitting layer/hole blocking layer/electron transport layer/electron injection layer/cathode'.
상기 애노드는 정공을 주입하는 전극으로, 애노드 물질로는 통상 유기물층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 본 발명에서 사용될 수 있는 애노드 물질의 구체적인 예로는 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물, 인듐주석 산화물(ITO, Indium Tin Oxide), 인듐아연 산화물(IZO, Indium Zinc Oxide)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 및 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDOT), 폴리피롤 및 폴리아닐린과 같은 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다.The anode is an electrode that injects holes, and the anode material is generally preferably a material with a large work function to ensure smooth hole injection into the organic layer. Specific examples of 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); Combinations of metals and oxides such as ZnO:Al or SnO 2 :Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited to these. .
상기 캐소드는 전자를 주입하는 전극으로, 캐소드 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 본 발명에서 사용될 수 있는 캐소드 물질의 구체적인 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 티타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이들에만 한정되는 것은 아니다.The cathode is an electrode that injects electrons, and 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 that can be used in the present invention include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; There are, but are not limited to, multi-layered materials such as LiF/Al or LiO 2 /Al.
상기 정공주입층은 애노드로부터 발광층으로 정공의 주입을 원활하게 하는 역할을 할 수 있다. 정공 주입 물질로는 낮은 전압에서 애노드로부터 정공을 잘 주입 받을 수 있는 물질로서, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 애노드의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrine), 올리고티오펜, 아릴아민 계열의 화합물, 헥사니트릴헥사아자트리페닐렌 계열의 화합물, 퀴나크리돈(quinacridone) 계열의 화합물, 페릴렌(perylene) 계열의 화합물, 벤조니트릴 계열의 화합물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. The hole injection layer may serve to facilitate the injection of holes from the anode to the light emitting layer. The hole injection material is a material that can easily inject holes from an anode at a low voltage, and it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the anode and the HOMO of the surrounding organic material layer. Specific examples of hole injection materials include metal porphyrine, oligothiophene, arylamine series compounds, hexanitrilehexaazatriphenylene series compounds, quinacridone series compounds, and perylene series. compounds, benzonitrile-based compounds, anthraquinone, and polyaniline- and polythiophene-based conductive polymers, but are not limited to these.
구체적으로, 상기 정공주입층은 아릴아민 계열의 화합물 및 벤조니트릴계열의 화합물이 사용될 수 있다. 보다 구체적으로, 카바졸기로 치환된 아릴아민계 화합물 및 할로겐기로 치환된 벤조니트릴계 화합물이 사용될 수 있으나, 이들에만 한정되는 것은 아니다. Specifically, the hole injection layer may be an arylamine-based compound or a benzonitrile-based compound. More specifically, arylamine-based compounds substituted with carbazole groups and benzonitrile-based compounds substituted with halogen groups may be used, but are not limited to these.
정공주입층의 두께는 1nm 내지 150nm일 수 있다. 상기 정공주입층의 두께가 1nm 이상이면, 정공 주입 특성이 저하되는 것을 방지할 수 있는 이점이 있고, 150nm 이하이면, 정공주입층의 두께가 너무 두꺼워 정공의 이동을 향상시키기 위해 구동전압이 상승되는 것을 방지할 수 있는 이점이 있다.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 deteriorating, and if it is 150 nm or less, the thickness of the hole injection layer is so thick that the driving voltage is increased to improve the movement of holes. There is an advantage to preventing this.
본 명세서의 일 실시상태에 따르면, 상기 정공주입층은 하기 화학식 HI-1의 화합물을 포함한다. According to an exemplary embodiment of the present specification, the hole injection layer includes a compound of the following formula HI-1.
[화학식 HI-1][Formula HI-1]
Figure PCTKR2023019646-appb-img-000027
Figure PCTKR2023019646-appb-img-000027
상기 화학식 HI-1에 있어서,In the formula HI-1,
L101은 직접결합; 또는 치환 또는 비치환된 아릴렌기이고,L101 is directly bonded; Or a substituted or unsubstituted arylene group,
R101 내지 R103은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이다.R101 to R103 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 따르면, 상기 L101은 직접결합; 치환 또는 비치환된 페닐렌기; 또는 치환 또는 비치환된 나프틸렌기이다.According to an exemplary embodiment of the present specification, L101 is a direct bond; Substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.
본 명세서의 일 실시상태에 따르면, 상기 L101은 직접결합; 또는 치환 또는 비치환된 페닐렌기이다.According to an exemplary embodiment of the present specification, L101 is a direct bond; Or a substituted or unsubstituted phenylene group.
본 명세서의 일 실시상태에 따르면, 상기 L101은 직접결합; 또는 페닐렌기이다.According to an exemplary embodiment of the present specification, L101 is a direct bond; Or it is a phenylene group.
본 명세서의 일 실시상태에 따르면, 상기 R101 내지 R103은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 단환의 아릴기; 또는 치환 또는 비치환된 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R101 to R103 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic aryl group; Or it is a substituted or unsubstituted polycyclic aryl group.
본 명세서의 일 실시상태에 따르면, 상기 R101 내지 R103은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라세닐기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 트리페닐레닐기; 치환 또는 비치환된 피렌기; 또는 치환 또는 비치환된 플루오레닐기이다. According to an exemplary embodiment of the present specification, R101 to R103 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted pyrene group; Or a substituted or unsubstituted fluorenyl group.
본 명세서의 일 실시상태에 따르면, 상기 R101 내지 R103은 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 또는 치환 또는 비치환된 플루오레닐기이다.According to an exemplary embodiment of the present specification, R101 to R103 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted fluorenyl group.
본 명세서의 일 실시상태에 따르면, 상기 R101 내지 R103은 서로 같거나 상이하고, 각각 독립적으로 페닐기; 바이페닐기; 또는 알킬기로 치환된 플루오레닐기이다.According to an exemplary embodiment of the present specification, R101 to R103 are the same as or different from each other, and are each independently a phenyl group; Biphenyl group; Or it is a fluorenyl group substituted with an alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HI-1은 하기 구조 중 어느 하나이다.According to an exemplary embodiment of the present specification, the formula HI-1 is one of the following structures.
Figure PCTKR2023019646-appb-img-000028
Figure PCTKR2023019646-appb-img-000028
본 명세서의 일 실시상태에 따르면, 상기 정공주입층은 하기 화학식 HI-2의 화합물을 포함한다. According to an exemplary embodiment of the present specification, the hole injection layer includes a compound of the following formula HI-2.
[화학식 HI-2][Formula HI-2]
Figure PCTKR2023019646-appb-img-000029
Figure PCTKR2023019646-appb-img-000029
상기 화학식 HI-2에 있어서,In the formula HI-2,
R111 내지 R113은 서로 같거나 상이하고, 각각 독립적으로 수소; 할로겐기; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,R111 to R113 are the same or different from each other, and are each independently hydrogen; halogen group; Nitrile group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
a111 내지 a113은 각각 1 내지 5의 정수이며,a111 to a113 are each integers from 1 to 5,
a111이 2 이상일 경우, 2 이상의 R111은 서로 같거나 상이하고,When a111 is 2 or more, 2 or more R111 are the same or different from each other,
a112가 2 이상일 경우, 2 이상의 R112는 서로 같거나 상이하며,When a112 is 2 or more, 2 or more R112 are the same or different from each other,
a113이 2 이상일 경우, 2 이상의 R113은 서로 같거나 상이하다.When a113 is 2 or more, 2 or more R113 are the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 R111 내지 R113은 서로 같거나 상이하고, 각각 할로겐기; 또는 니트릴기이다.According to an exemplary embodiment of the present specification, R111 to R113 are the same as or different from each other, and are each a halogen group; Or it is a nitrile group.
본 명세서의 일 실시상태에 따르면, 상기 R111 내지 R113은 서로 같거나 상이하고, 각각 불소; 또는 니트릴기이다.According to an exemplary embodiment of the present specification, R111 to R113 are the same or different from each other, and are each fluorine; Or it is a nitrile group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HI-2는 하기 구조이다.According to an exemplary embodiment of the present specification, the chemical formula HI-2 has the following structure.
Figure PCTKR2023019646-appb-img-000030
Figure PCTKR2023019646-appb-img-000030
본 명세서의 일 실시상태에 따르면, 상기 정공주입층은 상기 화학식 HI-1의 화합물 및 상기 화학식 HI-2의 화합물을 포함한다.According to an exemplary embodiment of the present specification, the hole injection layer includes a compound of the formula HI-1 and a compound of the formula HI-2.
상기 정공수송층은 정공의 수송을 원활하게 하는 역할을 할 수 있다. 정공 수송 물질로는 애노드나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 정공 수송 물질의 구체적인 예로는 아릴아민계 화합물, 카바졸계 화합물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. 구체적으로, 상기 정공수송층에는 아릴아민기로 치환된 카바졸계 화합물이 사용될 수 있으나, 이에만 한정되는 것은 아니다.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 of hole transport materials include, but are not limited to, arylamine-based compounds, carbazole-based compounds, conductive polymers, and block copolymers with both conjugated and non-conjugated parts. Specifically, a carbazole-based compound substituted with an arylamine group may be used in the hole transport layer, but is not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 정공수송층은 하기 화학식 HT-1의 화합물을 포함한다. According to an exemplary embodiment of the present specification, the hole transport layer includes a compound of the following formula HT-1.
[화학식 HT-1][Formula HT-1]
Figure PCTKR2023019646-appb-img-000031
Figure PCTKR2023019646-appb-img-000031
상기 화학식 HT-1에 있어서,In the formula HT-1,
L201 및 L202는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 아릴렌기이고,L201 and L202 are the same or different from each other and are each independently directly bonded; Or a substituted or unsubstituted arylene group,
R200은 치환 또는 비치환된 아릴기이며,R200 is a substituted or unsubstituted aryl group,
R201 내지 R204는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.R201 to R204 are the same or different from each other, and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.
본 명세서의 일 실시상태에 따르면, 상기 L201 및 L202는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴렌기이다.According to an exemplary embodiment of the present specification, L201 and L202 are the same or different from each other and are each independently a substituted or unsubstituted arylene group.
본 명세서의 일 실시상태에 따르면, 상기 L201 및 L202는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐렌기; 또는 치환 또는 비치환된 나프틸렌기이다.According to an exemplary embodiment of the present specification, L201 and L202 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.
본 명세서의 일 실시상태에 따르면, 상기 L201 및 L202는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐렌기이다.According to an exemplary embodiment of the present specification, L201 and L202 are the same or different from each other and are each independently a substituted or unsubstituted phenylene group.
본 명세서의 일 실시상태에 따르면, 상기 L201 및 L202는 각각 페닐렌기이다.According to an exemplary embodiment of the present specification, L201 and L202 are each a phenylene group.
본 명세서의 일 실시상태에 따르면, 상기 R200은 치환 또는 비치환된 단환의 아릴기; 또는 치환 또는 비치환된 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R200 is a substituted or unsubstituted monocyclic aryl group; Or it is a substituted or unsubstituted polycyclic aryl group.
본 명세서의 일 실시상태에 따르면, 상기 R200은 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라세닐기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 트리페닐레닐기; 치환 또는 비치환된 피렌기; 또는 치환 또는 비치환된 플루오레닐기이다. According to an exemplary embodiment of the present specification, R200 is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted pyrene group; Or a substituted or unsubstituted fluorenyl group.
본 명세서의 일 실시상태에 따르면, 상기 R200은 치환 또는 비치환된 나프틸기이다.According to an exemplary embodiment of the present specification, R200 is a substituted or unsubstituted naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 R201 내지 R204는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이다.According to an exemplary embodiment of the present specification, R201 to R204 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 따르면, 상기 R201 내지 R204는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 단환의 아릴기; 또는 치환 또는 비치환된 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R201 to R204 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic aryl group; Or it is a substituted or unsubstituted polycyclic aryl group.
본 명세서의 일 실시상태에 따르면, 상기 R201 내지 R204는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라세닐기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 트리페닐레닐기; 치환 또는 비치환된 피렌기; 또는 치환 또는 비치환된 플루오레닐기이다. According to an exemplary embodiment of the present specification, R201 to R204 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted pyrene group; Or a substituted or unsubstituted fluorenyl group.
본 명세서의 일 실시상태에 따르면, 상기 R201 내지 R204는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기이다.According to an exemplary embodiment of the present specification, R201 to R204 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 R201 내지 R204는 각각 페닐기이다.According to an exemplary embodiment of the present specification, R201 to R204 are each a phenyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HT-1은 하기 구조이다.According to an exemplary embodiment of the present specification, the chemical formula HT-1 has the following structure.
Figure PCTKR2023019646-appb-img-000032
Figure PCTKR2023019646-appb-img-000032
상기 정공주입층과 정공수송층 사이에 추가로 정공버퍼층이 구비될 수 있으며, 당 기술분야에 알려져 있는 정공주입 또는 수송재료를 포함할 수 있다. 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.
상기 정공수송층과 발광층 사이에 전자차단층이 구비될 수 있다. 상기 전자차단층에는 전술한 화합물 또는 당 기술분야에 알려져 있는 재료가 사용될 수 있다. 구체적으로, 상기 전자차단층에는 카바졸계 화합물이 사용될 수 있다.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. Specifically, a carbazole-based compound may be used in the electron blocking layer.
본 명세서의 일 실시상태에 따르면, 상기 전자차단층은 하기 화학식 EB-1의 화합물을 포함한다. According to an exemplary embodiment of the present specification, the electron blocking layer includes a compound of the following formula EB-1.
[화학식 EB-1][Formula EB-1]
Figure PCTKR2023019646-appb-img-000033
Figure PCTKR2023019646-appb-img-000033
상기 화학식 EB-1에 있어서,In the formula EB-1,
L301은 치환 또는 비치환된 아릴렌기이고,L301 is a substituted or unsubstituted arylene group,
R301 및 R302는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이다.R301 and R302 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 따르면, 상기 L301은 단환 또는 다환의 아릴렌기이다.According to an exemplary embodiment of the present specification, L301 is a monocyclic or polycyclic arylene group.
본 명세서의 일 실시상태에 따르면, 상기 L301은 치환 또는 비치환된 페닐렌기; 또는 치환 또는 비치환된 바이페닐렌기이다.According to an exemplary embodiment of the present specification, L301 is a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.
본 명세서의 일 실시상태에 따르면, 상기 L301은 바이페닐렌기이다.According to an exemplary embodiment of the present specification, L301 is a biphenylene group.
본 명세서의 일 실시상태에 따르면, 상기 R301 및 R302는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라세닐기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 트리페닐레닐기; 치환 또는 비치환된 피렌기; 또는 치환 또는 비치환된 플루오레닐기이다. According to an exemplary embodiment of the present specification, R301 and R302 are the same or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted pyrene group; Or a substituted or unsubstituted fluorenyl group.
본 명세서의 일 실시상태에 따르면, 상기 R301 및 R302는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 또는 치환 또는 비치환된 바이페닐기이다.According to an exemplary embodiment of the present specification, R301 and R302 are the same or different from each other, and are each independently a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted biphenyl group.
본 명세서의 일 실시상태에 따르면, 상기 R301 및 R302는 서로 같거나 상이하고, 각각 독립적으로 아릴기로 치환 또는 비치환된 바이페닐기이다.According to an exemplary embodiment of the present specification, R301 and R302 are the same or different from each other, and each independently represents a biphenyl group substituted or unsubstituted by an aryl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 EB-1은 하기 구조이다.According to an exemplary embodiment of the present specification, the formula EB-1 has the following structure.
Figure PCTKR2023019646-appb-img-000034
Figure PCTKR2023019646-appb-img-000034
상기 발광층은 적색, 녹색 또는 청색을 발광할 수 있으며, 인광 물질 또는 형광 물질로 이루어질 수 있다. 상기 발광 물질로는 정공수송층과 전자수송층으로부터 정공과 전자를 각각 수송 받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 예컨대, 상기 발광 물질로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카바졸 계열 화합물; 이량체화 스티릴(dimerized styryl) 화합물; BAlq; 10-히드록시벤조 퀴놀린-금속 화합물; 벤족사졸, 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리(p-페닐렌비닐렌)(PPV) 계열의 고분자; 스피로(spiro) 화합물; 폴리플루오렌; 루브렌 등이 있으나, 이들에만 한정되는 것은 아니다.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. For example, the light-emitting material includes 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 is not limited to these.
발광층의 호스트 재료로는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 예컨대, 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이들에만 한정되는 것은 아니다. 구체적으로, 상기 발광층의 호스트로는 본 발명의 화학식 1의 화합물이 사용될 수 있으나, 이에만 한정되는 것은 아니다.Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocycle-containing compounds. For example, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder-type compounds. These include furan compounds and pyrimidine derivatives, but are not limited to these. Specifically, the compound of Formula 1 of the present invention may be used as the host of the light-emitting layer, but is not limited thereto.
발광층이 적색 발광을 하는 경우, 발광 도펀트로는 PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum)와 같은 인광 물질이나, Alq3(tris(8-hydroxyquinolino)aluminum)와 같은 형광 물질이 사용될 수 있으나, 이들에만 한정되는 것은 아니다. 발광층이 녹색 발광을 하는 경우, 발광 도펀트로는 Ir(ppy)3(tris(2-phenylpyridine)iridium)와 같은 인광물질이나, Alq3(tris(8-hydroxyquinolino)aluminum)와 같은 형광 물질이 사용될 수 있으나, 이들에만 한정되는 것은 아니다. 발광층이 청색 발광을 하는 경우, 발광 도펀트로는 (4,6-F2ppy)2Irpic와 같은 인광 물질이나, spiro-DPVBi, spiro-6P, 디스틸벤젠(DSB), 디스트릴아릴렌(DSA), 피렌계 화합물, PFO계 고분자, PPV계 고분자와 같은 형광 물질이 사용될 수 있으나, 이들에만 한정되는 것은 아니다. 구체적으로, 상기 도펀트로는 피렌계 화합물이 사용될 수 있으나, 이에만 한정되는 것은 아니다.When the light-emitting layer emits red light, the light-emitting dopants include PIQIr(acac)(bis(1-phenylquinoline)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. If the light-emitting layer emits green light, a phosphor such as Ir(ppy) 3 (tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum) can be used as the light-emitting dopant. However, it is not limited to these. If the light-emitting layer emits blue light, the light-emitting dopant may be a phosphorescent material such as (4,6-F 2 ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), or distrylarylene (DSA). ), pyrene-based compounds, PFO-based polymers, and PPV-based polymers may be used, but are not limited to these. Specifically, a pyrene-based compound may be used as the dopant, but is not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 도펀트는 하기 화학식 D의 화합물을 포함한다. According to an exemplary embodiment of the present specification, the dopant includes a compound of formula D below.
[화학식 D][Formula D]
Figure PCTKR2023019646-appb-img-000035
Figure PCTKR2023019646-appb-img-000035
상기 화학식 D에 있어서,In Formula D,
X1 및 X2는 서로 같거나 상이하고, 각각 독립적으로 CR'; 또는 NR"이고, X1 및 X2 중 적어도 하나는 NR"이며, X1 and X2 are the same or different from each other and are each independently CR'; or NR", and at least one of X1 and X2 is NR",
R401 내지 R403, R' 및 R"은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접한 기와 서로 결합하여, 치환 또는 비치환된 고리를 형성하고,R401 to R403, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; halogen group; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkoxy A substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; Thus, forming a substituted or unsubstituted ring,
r401 및 r403은 각각 0 내지 4의 정수이고, r402는 0 내지 3의 정수이고, r401 내지 r403이 각각 2 이상인 경우 괄호 내의 치환기는 서로 같거나 상이하다.r401 and r403 are each an integer from 0 to 4, r402 is an integer from 0 to 3, and when r401 to r403 are each 2 or more, the substituents in the parentheses are the same or different from each other.
본 명세서의 일 실시상태에 따르면, 상기 R401 내지 R403은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 또는 치환 또는 비치환된 아릴기이다.According to an exemplary embodiment of the present specification, R401 to R403 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.
본 명세서의 일 실시상태에 따르면, 상기 R401 내지 R403은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 치환 또는 비치환된 알킬기이다.According to an exemplary embodiment of the present specification, R401 to R403 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a substituted or unsubstituted alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 R401 내지 R403은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 직쇄 또는 분지쇄의 알킬기이다.According to an exemplary embodiment of the present specification, R401 to R403 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a straight chain or branched alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 R401 내지 R403은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 탄소수 1 내지 30의 직쇄의 알킬기; 또는 탄소수 4 내지 30의 분지쇄의 알킬기이다.According to an exemplary embodiment of the present specification, R401 to R403 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; A straight-chain alkyl group having 1 to 30 carbon atoms; Or it is a branched alkyl group having 4 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 R401 내지 R403은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 또는 탄소수 4 내지 30의 분지쇄의 알킬기이다.According to an exemplary embodiment of the present specification, R401 to R403 are the same as or different from each other, and are each independently hydrogen; heavy hydrogen; Or it is a branched alkyl group having 4 to 30 carbon atoms.
본 명세서의 일 실시상태에 따르면, 상기 X1 및 X2는 서로 같거나 상이하고, 각각 독립적으로 NR''이고, R''은 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.According to an exemplary embodiment of the present specification, X1 and X2 are the same or different from each other and are each independently NR'', and R'' is a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.
본 명세서의 일 실시상태에 따르면, 상기 X1 및 X2는 서로 같거나 상이하고, 각각 독립적으로 NR''이고, R''은 치환 또는 비치환된 아릴기이다.According to an exemplary embodiment of the present specification, X1 and X2 are the same or different from each other and are each independently NR'', and R'' is a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 따르면, 상기 X1 및 X2는 서로 같거나 상이하고, 각각 독립적으로 NR''이고, R''은 알킬기로 치환된 아릴기이다.According to an exemplary embodiment of the present specification, X1 and X2 are the same or different from each other and are each independently NR'', and R'' is an aryl group substituted with an alkyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 D는 하기 구조이다.According to an exemplary embodiment of the present specification, Formula D has the following structure.
Figure PCTKR2023019646-appb-img-000036
Figure PCTKR2023019646-appb-img-000036
본 명세서의 일 실시상태에 따르면, 상기 발광층은 상기 화학식 1의 화합물을 발광층의 호스트로 포함하고, 상기 화학식 D의 화합물을 발광층의 도펀트로 포함한다.According to an exemplary embodiment of the present specification, the light-emitting layer includes the compound of Formula 1 as a host of the light-emitting layer, and the compound of Formula D as a dopant of the light-emitting layer.
본 발명의 일 실시상태에 따르면, 상기 발광층 내에서 상기 화학식 1의 화합물과 상기 화학식 D의 화합물의 중량비는 100:1 내지 1:1이다. 구체적으로, 70:1 내지 2:1, 또는 50:1 내지 3:1이다. According to an exemplary embodiment of the present invention, the weight ratio of the compound of Formula 1 and the compound of Formula D in the light emitting layer is 100:1 to 1:1. Specifically, 70:1 to 2:1, or 50:1 to 3:1.
상기 캐소드와 발광층 사이에 정공차단층이 구비될 수 있다. 상기 정공차단층은 정공의 캐소드 도달을 저지하는 층으로, 일반적으로 정공주입층과 동일한 조건으로 형성될 수 있다. 정공 차단 물질의 구체적인 예로는 옥사디아졸 유도체나 트리아졸 유도체, 트리아진 유도체, 페난트롤린 유도체, BCP, 알루미늄 착물 (aluminum complex) 등이 있으나, 이들에만 한정되는 것은 아니다. 구체적으로, 트리아진 유도체가 사용될 수 있으나, 이에만 한정되는 것은 아니다.A hole blocking layer may be provided between the cathode and the light emitting layer. 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. Specific examples of hole blocking materials include, but are not limited to, oxadiazole derivatives, triazole derivatives, triazine derivatives, phenanthroline derivatives, BCP, and aluminum complexes. Specifically, triazine derivatives may be used, but are not limited thereto.
본 명세서의 일 실시상태에 따르면, 상기 정공차단층는 하기 화학식 HB-1의 화합물을 포함한다. According to an exemplary embodiment of the present specification, the hole blocking layer includes a compound of the following formula HB-1.
[화학식 HB-1][Formula HB-1]
Figure PCTKR2023019646-appb-img-000037
Figure PCTKR2023019646-appb-img-000037
상기 화학식 HB-1에 있어서,In the formula HB-1,
L501 내지 L503은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 아릴렌기이고,L501 to L503 are the same or different from each other and are each independently directly bonded; Or a substituted or unsubstituted arylene group,
R501 내지 R504는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.R501 to R504 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or it is a substituted or unsubstituted heterocyclic group.
본 명세서의 일 실시상태에 따르면, 상기 L501 내지 L503은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 치환 또는 비치환된 페닐렌기; 치환 또는 비치환된 바이페닐렌기; 또는 치환 또는 비치환된 나프틸렌기이다.According to an exemplary embodiment of the present specification, L501 to L503 are the same or different from each other and are each independently directly bonded; Substituted or unsubstituted phenylene group; Substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted naphthylene group.
본 명세서의 일 실시상태에 따르면, 상기 L501 내지 L503은 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 치환 또는 비치환된 바이페닐렌기이다.According to an exemplary embodiment of the present specification, L501 to L503 are the same or different from each other and are each independently directly bonded; Or a substituted or unsubstituted biphenylene group.
본 명세서의 일 실시상태에 따르면, 상기 L501 및 L502는 서로 같거나 상이하고, 각각 독립적으로 직접결합이다.According to an exemplary embodiment of the present specification, L501 and L502 are the same or different from each other and are each independently a direct bond.
본 명세서의 일 실시상태에 따르면, 상기 L503은 치환 또는 비치환된 바이페닐렌기이다.According to an exemplary embodiment of the present specification, L503 is a substituted or unsubstituted biphenylene group.
본 명세서의 일 실시상태에 따르면, 상기 L503은 바이페닐렌기이다.According to an exemplary embodiment of the present specification, L503 is a biphenylene group.
본 명세서의 일 실시상태에 따르면, 상기 R501 내지 R504는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기이다.According to an exemplary embodiment of the present specification, R501 to R504 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group.
본 명세서의 일 실시상태에 따르면, 상기 R501 내지 R504는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 단환의 아릴기; 또는 치환 또는 비치환된 다환의 아릴기이다.According to an exemplary embodiment of the present specification, R501 to R504 are the same or different from each other, and are each independently a substituted or unsubstituted monocyclic aryl group; Or it is a substituted or unsubstituted polycyclic aryl group.
본 명세서의 일 실시상태에 따르면, 상기 R501 내지 R504는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 안트라세닐기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 트리페닐레닐기; 치환 또는 비치환된 피렌기; 또는 치환 또는 비치환된 플루오레닐기이다. According to an exemplary embodiment of the present specification, R501 to R504 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted pyrene group; Or a substituted or unsubstituted fluorenyl group.
본 명세서의 일 실시상태에 따르면, 상기 R501 내지 R504는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 페닐기; 또는 치환 또는 비치환된 나프틸기이다.According to an exemplary embodiment of the present specification, R501 to R504 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; Or a substituted or unsubstituted naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 R501 내지 R504는 서로 같거나 상이하고, 각각 독립적으로 나프틸기로 치환 또는 비치환된 페닐기이다.According to an exemplary embodiment of the present specification, R501 to R504 are the same as or different from each other, and each independently represents a phenyl group substituted or unsubstituted by a naphthyl group.
본 명세서의 일 실시상태에 따르면, 상기 화학식 HB-1은 하기 구조 중 어느 하나이다.According to an exemplary embodiment of the present specification, the formula HB-1 is one of the following structures.
Figure PCTKR2023019646-appb-img-000038
Figure PCTKR2023019646-appb-img-000038
상기 전자수송층은 전자의 수송을 원활하게 하는 역할을 할 수 있다. 전자 수송 물질로는 캐소드로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서, 전자에 대한 이동성이 큰 물질이 적합하다. 예컨대, 상기 전자 수송 물질로는 8-히드록시퀴놀린의 Al 착물, Alq3를 포함한 착물, 유기 라디칼 화합물, 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자수송층의 두께는 1nm 내지 50nm일 수 있다. 전자수송층의 두께가 1nm 이상이면 전자 수송 특성이 저하되는 것을 방지할 수 있는 이점이 있고, 50nm 이하이면 전자수송층의 두께가 너무 두꺼워 전자의 이동을 향상시키기 위해 구동전압이 상승되는 것을 방지할 수 있는 이점이 있다.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. For example, the electron transport material includes, but is not limited to, an Al complex of 8-hydroxyquinoline, a complex containing Alq 3 , an organic radical compound, and a hydroxyflavone-metal complex. The thickness of the electron transport layer may be 1 nm to 50 nm. If the thickness of the electron transport layer is 1 nm or more, it has the advantage of 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 to prevent the driving voltage from increasing to improve the movement of electrons. There is an advantage.
상기 전자주입층은 전자의 주입을 원활하게 하는 역할을 할 수 있다. 전자 주입 물질로는 전자를 수송하는 능력을 갖고, 캐소드로부터의 전자주입 효과, 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며, 발광층에서 생성된 여기자의 정공 주입층에의 이동을 방지하고, 박막형성능력이 우수한 화합물이 바람직하다. 예컨대, 상기 전자 주입 물질로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 트리아진, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 함질소 5원환 유도체 등이 있으나, 이에 한정되지 않는다.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, a light emitting layer or a light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, and thin film Compounds with excellent forming ability are preferred. For example, the electron injection materials include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, triazine, imidazole, perylenetetracarboxylic acid, and preorenylidene methane. , anthrone, etc. and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives, etc., but are not limited thereto.
상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬, 비스(8-하이드록시퀴놀리나토)아연, 비스(8-하이드록시퀴놀리나토)구리, 비스(8-하이드록시퀴놀리나토)망간, 트리스(8-하이드록시퀴놀리나토)알루미늄, 트리스(2-메틸-8-하이드록시퀴놀리나토)알루미늄, 트리스(8-하이드록시퀴놀리나토)갈륨, 비스(10-하이드록시벤조[h]퀴놀리나토)베릴륨, 비스(10-하이드록시벤조[h]퀴놀리나토)아연, 비스(2-메틸-8-퀴놀리나토)클로로갈륨, 비스(2-메틸-8-퀴놀리나토)(o-크레졸라토)갈륨, 비스(2-메틸-8-퀴놀리나토)(1-나프톨라토)알루미늄, 비스(2-메틸-8-퀴놀리나토)(2-나프톨라토)갈륨 등이 있으나, 이에 한정되지 않는다.Examples of the 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.
상기 전자수송층 및 전자주입층은 단층으로 형성될 수 있다. 예컨대, 전자 주입 물질과 전자 수송 물질을 동시에 진공증착하거나, 전자 주입 및 수송 효과를 동시에 나타내는 물질을 진공증착하여 전자 주입 및 수송층을 형성할 수 있다.The electron transport layer and electron injection layer may be formed as a single layer. For example, an electron injection and transport layer can be formed by vacuum depositing an electron injection material and an electron transport material at the same time, or by vacuum depositing a material that exhibits both electron injection and transport effects.
상기 전자주입 및 수송층은 금속 착체를 더 포함할 수 있다. 상기 금속 착체의 예로는 8-히드록시퀴놀린의 Al 착물(Alq3), LiQ, 금속 착체 화합물 등이 있으나, 이에만 한정되지 않는다. 예컨대, 상기 전자 주입 및 수송층은 트리아진 유도체와 리튬퀴놀라이트(LiQ)가 사용될 수 있으나, 이에만 한정되는 것은 아니다.The electron injection and transport layer may further include a metal complex. Examples of the metal complex include, but are not limited to, Al complex of 8-hydroxyquinoline (Alq 3 ), LiQ, and metal complex compounds. For example, the electron injection and transport layer may be made of triazine derivatives and lithium quinolite (LiQ), but is not limited thereto.
본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형, 후면 발광형 또는 양면 발광형일 수 있다.The organic light emitting device according to the present invention may be a front emitting type, a back emitting type, or a double-sided emitting type depending on the material used.
또한, 본 명세서에 따른 유기 발광 소자는 다양한 전자 장치에 포함되어 사용될 수 있다. 예컨대, 상기 전자 장치는 디스플레이 패널, 터치 패널, 태양광 모듈, 조명 장치 등일 수 있고, 이에 한정되지 않는다.Additionally, the organic light emitting device according to the present specification can be included and used in various electronic devices. For example, the electronic device may be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.
이하, 본 명세서를 구체적으로 설명하기 위해 실험예를 들어 상세하기 설명하기로 한다. 그러나, 본 명세서에 따른 실시예들은 여러가지 다른 형태로 변형될 수 있으며, 본 출원의 범위가 아래에서 상술하는 실시예들에 한정되는 것으로 해석되지 않는다. 본 출원의 실시예들은 당업계에서 평균적인 지식을 가진 자에게 본 명세서를 보다 완전하게 설명하기 위해 제공되는 것이다.Hereinafter, an experimental example will be used to explain the present specification in detail. However, the embodiments according to the present specification may be modified in various other forms, and the scope of the present application is not to be construed as being limited to the embodiments described in detail below. The embodiments of this application are provided to more completely explain the present specification to those with average knowledge in the art.
<< 제조예Manufacturing example 1> 화합물 1의 합성 1> Synthesis of Compound 1
Figure PCTKR2023019646-appb-img-000039
Figure PCTKR2023019646-appb-img-000039
질소 분위기에서 500 mL 둥근 바닥 플라스크에 9-브로모-10-(나프탈렌-1-일)안트라센(9-bromo-10-(naphthalen-1-yl)anthracene) (6.50 g, 16.97 mmol), 및 화합물 a-1(8.33 g, 18.67 mmol)을 테트라하이드로퓨란 240 mL에 완전히 녹인 후 2M 탄산칼륨수용액(120 mL)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(Pd(PPh3)4) (0.59 g, 0.51 mmol)을 넣은 후 2시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 톨루엔 250 mL로 재결정하여 화합물 1(5.99 g, 수율: 57%)을 제조하였다. MS[M+H]+= 6239-bromo-10-(naphthalen-1-yl)anthracene (6.50 g, 16.97 mmol), and compound in a 500 mL round bottom flask in a nitrogen atmosphere. After completely dissolving a-1 (8.33 g, 18.67 mmol) in 240 mL of tetrahydrofuran, 2M aqueous potassium carbonate solution (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (Pd(PPh 3 ) 4 ) (0.59 g, 0.51 mmol) was added and heated and stirred for 2 hours. The temperature was lowered to room temperature, the water layer was removed, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized from 250 mL of toluene to prepare Compound 1 (5.99 g, yield: 57%). MS[M+H] + = 623
<< 제조예Manufacturing example 2> 화합물 2의 화합물 합성 2> Compound synthesis of compound 2
Figure PCTKR2023019646-appb-img-000040
Figure PCTKR2023019646-appb-img-000040
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-브로모-10-(나프탈렌-2-일)안트라센(9-bromo-10-(naphthalen-2-yl)anthracene) (6.50 g, 16.97 mmol), 및 화합물 a-2(8.33 g, 18.67 mmol)을 테트라하이드로퓨란 240 mL에 완전히 녹인 후 2M 탄산칼륨수용액(120 mL)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.59 g, 0.51 mmol)을 넣은 후 4시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 톨루엔 310 mL로 재결정하여 화합물 2(6.23 g, 수율: 59%)를 제조하였다. MS[M+H]+= 623Compound 9-bromo-10-(naphthalen-2-yl)anthracene (6.50 g, 16.97 mmol) in a 500 mL round bottom flask in a nitrogen atmosphere, and Compound a-2 (8.33 g, 18.67 mmol) was completely dissolved in 240 mL of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (0.59 g, 0.51 mmol) was added. After being added, it was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 310 mL of toluene to prepare Compound 2 (6.23 g, yield: 59%). MS[M+H] + = 623
<< 제조예Manufacturing example 3> 화합물 3의 화합물 합성 3> Compound synthesis of compound 3
Figure PCTKR2023019646-appb-img-000041
Figure PCTKR2023019646-appb-img-000041
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-브로모-10-(페난트렌-9-일)안트라센(9-bromo-10-(phenanthren-9-yl)anthracene) (6.50 g, 16.51 mmol), 및 화합물 a-3(9.26 g, 18.67 mmol)을 테트라하이드로퓨란 240 mL에 완전히 녹인 후 2M 탄산칼륨수용액(120 mL)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.59 g, 0.51 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 톨루엔 240 mL로 재결정하여 화합물 3(6.44 g, 수율: 56%)을 제조하였다. MS[M+H]+= 673Compound 9-bromo-10-(phenanthren-9-yl)anthracene (6.50 g, 16.51 mmol) in a 500 mL round bottom flask in a nitrogen atmosphere. and Compound a-3 (9.26 g, 18.67 mmol) was completely dissolved in 240 mL of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (0.59 g, 0.51 mmol) was added. ) was added and then heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 mL of toluene to prepare Compound 3 (6.44 g, yield: 56%). MS[M+H] + = 673
<< 제조예Manufacturing example 4> 화합물 4의 화합물 합성 4> Compound synthesis of compound 4
Figure PCTKR2023019646-appb-img-000042
Figure PCTKR2023019646-appb-img-000042
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-브로모-10-페닐안트라센-1,2,3,4,5,6,7,8-d8(9-bromo-10-phenylanthracene-1,2,3,4,5,6,7,8-d8) (6.50 g, 19.06 mmol), 및 화합물 a-1(9.35 g, 20.97 mmol)을 테트라하이드로퓨란 240 mL에 완전히 녹인 후 2M 탄산칼륨수용액(120 mL)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.66 g, 0.57 mmol)을 넣은 후 4시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 톨루엔 270 mL로 재결정하여 화합물 4(6.51 g, 수율: 59%)를 제조하였다. MS[M+H]+= 581Compound 9-bromo-10-phenylanthracene-1,2,3,4,5,6,7,8-d8 (9-bromo-10-phenylanthracene-1,2, 3,4,5,6,7,8-d8) (6.50 g, 19.06 mmol), and compound a-1 (9.35 g, 20.97 mmol) were completely dissolved in 240 mL of tetrahydrofuran and then dissolved in 2M aqueous potassium carbonate solution (120 mL). mL) was added, tetrakis-(triphenylphosphine)palladium (0.66 g, 0.57 mmol) was added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 270 mL of toluene to prepare Compound 4 (6.51 g, yield: 59%). MS[M+H] + = 581
<< 제조예Manufacturing example 5> 화합물 5의 화합물 합성 5> Compound synthesis of compound 5
Figure PCTKR2023019646-appb-img-000043
Figure PCTKR2023019646-appb-img-000043
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-([1,1'-바이페닐]-4-일)-10-브로모안트라센-1,2,3,4,5,6,7,8-d8(9-([1,1'-biphenyl]-4-yl)-10-bromoanthracene-1,2,3,4,5,6,7,8-d8) (6.50 g, 15.85 mmol), 및 화합물 a-2(7.78 g, 17.44 mmol)을 테트라하이드로퓨란 240 mL에 완전히 녹인 후 2M 탄산칼륨수용액(120 mL)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.55 g, 0.48 mmol)을 넣은 후 4시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 톨루엔 250 mL로 재결정하여 화합물 5(7.06 g, 수율: 68%)를 제조하였다. MS[M+H]+= 657Compound 9-([1,1'-biphenyl]-4-yl)-10-bromoanthracene-1,2,3,4,5,6,7,8- in a 500 mL round bottom flask under nitrogen atmosphere. d8(9-([1,1'-biphenyl]-4-yl)-10-bromoanthracene-1,2,3,4,5,6,7,8-d8) (6.50 g, 15.85 mmol), and Compound a-2 (7.78 g, 17.44 mmol) was completely dissolved in 240 mL of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (0.55 g, 0.48 mmol) was added. After being added, it was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 250 mL of toluene to prepare Compound 5 (7.06 g, yield: 68%). MS[M+H] + = 657
<< 제조예Manufacturing example 6> 화합물 6의 화합물 합성 6> Compound synthesis of compound 6
Figure PCTKR2023019646-appb-img-000044
Figure PCTKR2023019646-appb-img-000044
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-([1,1'-바이페닐]3-일)-10-브로모안트라센-1,2,3,4,5,6,7,8-d8(9-([1,1'-biphenyl]-3-yl)-10-bromoanthracene-1,2,3,4,5,6,7,8-d8) (6.50 g, 15.85 mmol), 및 화합물 a-3(7.78 g, 17.44 mmol)을 테트라하이드로퓨란 240 mL에 완전히 녹인 후 2M 탄산칼륨수용액(120 mL)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.55 g, 0.48 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 톨루엔 260 mL로 재결정하여 화합물 6(7.34 g, 수율: 70%)을 제조하였다. MS[M+H]+= 657Compound 9-([1,1'-biphenyl]3-yl)-10-bromoanthracene-1,2,3,4,5,6,7,8-d8 in a 500 mL round bottom flask under nitrogen atmosphere. (9-([1,1'-biphenyl]-3-yl)-10-bromoanthracene-1,2,3,4,5,6,7,8-d8) (6.50 g, 15.85 mmol), and compounds After completely dissolving a-3 (7.78 g, 17.44 mmol) in 240 mL of tetrahydrofuran, 2M aqueous potassium carbonate solution (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (0.55 g, 0.48 mmol) was added. After addition, it was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 260 mL of toluene to prepare Compound 6 (7.34 g, yield: 70%). MS[M+H] + = 657
<< 제조예Manufacturing example 7> 화합물 7의 화합물 합성 7> Compound synthesis of compound 7
Figure PCTKR2023019646-appb-img-000045
Figure PCTKR2023019646-appb-img-000045
질소 분위기에서 500 mL 둥근 바닥 플라스크에 9-([1,1'-바이페닐]-2-일-d9)-10-브로모안트라센-1,2,3,4,5,6,7,8-d8(9-([1,1'-biphenyl]-2-yl-d9)-10-bromoanthracene-1,2,3,4,5,6,7,8-d8) (6.50 g, 15.26 mmol), 및 화합물 a-4(7.74 g, 16.78 mmol)을 테트라하이드로퓨란 240 mL에 완전히 녹인 후 2M 탄산칼륨수용액(120 mL)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.53 g, 0.46 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 톨루엔 270 mL로 재결정하여 화합물 7(6.89 g, 수율: 66%)을 제조하였다. MS[M+H]+= 6829-([1,1'-biphenyl]-2-yl-d9)-10-bromoanthracene-1,2,3,4,5,6,7,8 in a 500 mL round bottom flask under nitrogen atmosphere. -d8(9-([1,1'-biphenyl]-2-yl-d9)-10-bromoanthracene-1,2,3,4,5,6,7,8-d8) (6.50 g, 15.26 mmol ), and Compound a-4 (7.74 g, 16.78 mmol) were completely dissolved in 240 mL of tetrahydrofuran, then 2M potassium carbonate aqueous solution (120 mL) was added, and tetrakis-(triphenylphosphine)palladium (0.53 g, 0.46 mmol) was added and then heated and stirred for 3 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 270 mL of toluene to prepare Compound 7 (6.89 g, yield: 66%). MS[M+H] + = 682
<< 제조예Manufacturing example 8> 화합물 8의 화합물 합성 8> Compound synthesis of compound 8
Figure PCTKR2023019646-appb-img-000046
Figure PCTKR2023019646-appb-img-000046
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 3-(10-브로모안트라센-9-일-1,2,3,4,5,6,7,8-d8)디벤조[b,d]퓨란-1,2,4,6,7,8,9-d7(3-(10-bromoanthracen-9-yl-1,2,3,4,5,6,7,8-d8)dibenzo[b,d]furan-1,2,4,6,7,8,9-d7) (6.50 g, 14.84 mmol), 및 화합물 a-1(7.28 g, 16.32 mmol)을 테트라하이드로퓨란 240 mL에 완전히 녹인 후 2M 탄산칼륨수용액(120 mL)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.51 g, 0.45 mmol)을 넣은 후 4시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 톨루엔 270 mL로 재결정하여 화합물 8(6.13 g, 수율: 61%)을 제조하였다. MS[M+H]+= 678Compound 3-(10-bromoanthracen-9-yl-1,2,3,4,5,6,7,8-d8)dibenzo[b,d]furan- was added to a 500 mL round bottom flask in a nitrogen atmosphere. 1,2,4,6,7,8,9-d7(3-(10-bromoanthracen-9-yl-1,2,3,4,5,6,7,8-d8)dibenzo[b,d ]furan-1,2,4,6,7,8,9-d7) (6.50 g, 14.84 mmol), and compound a-1 (7.28 g, 16.32 mmol) were completely dissolved in 240 mL of tetrahydrofuran and then dissolved in 2M An aqueous potassium carbonate solution (120 mL) was added, tetrakis-(triphenylphosphine)palladium (0.51 g, 0.45 mmol) was added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 270 mL of toluene to prepare Compound 8 (6.13 g, yield: 61%). MS[M+H] + = 678
<< 제조예Manufacturing example 9> 화합물 9의 화합물 합성 9> Compound synthesis of compound 9
Figure PCTKR2023019646-appb-img-000047
Figure PCTKR2023019646-appb-img-000047
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 7-(10-브로모안트라센-9-일-1,2,3,4,5,6,7,8-d8)나프토[1,2-b]벤조퓨란-1,2,3,4,5,6,8,10-d8(7-(10-bromoanthracen-9-yl-1,2,3,4,5,6,7,8-d8)naphtho[1,2-b]benzofuran-1,2,3,4,5,6,8,10-d8) (6.50 g, 13.29 mmol), 및 화합물 a-2(6.52 g, 14.62 mmol)을 테트라하이드로퓨란 240 mL에 완전히 녹인 후 2M 탄산칼륨수용액(120 mL)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.46 g, 0.40 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 톨루엔 240 mL로 재결정하여 화합물 9(6.75 g, 수율: 70%)를 제조하였다. MS[M+H]+= 729Compound 7-(10-bromoanthracen-9-yl-1,2,3,4,5,6,7,8-d8)naphtho[1,2-b] was added to a 500 mL round bottom flask under nitrogen atmosphere. Benzofuran-1,2,3,4,5,6,8,10-d8(7-(10-bromoanthracen-9-yl-1,2,3,4,5,6,7,8-d8) naphtho[1,2-b]benzofuran-1,2,3,4,5,6,8,10-d8) (6.50 g, 13.29 mmol), and compound a-2 (6.52 g, 14.62 mmol) were added to tetra After completely dissolving in 240 mL of hydrofuran, 2M aqueous potassium carbonate solution (120 mL) was added, tetrakis-(triphenylphosphine)palladium (0.46 g, 0.40 mmol) was added, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 240 mL of toluene to prepare Compound 9 (6.75 g, yield: 70%). MS[M+H] + = 729
<< 제조예Manufacturing example 10> 화합물 10의 화합물 합성 10> Compound synthesis of compound 10
Figure PCTKR2023019646-appb-img-000048
Figure PCTKR2023019646-appb-img-000048
질소 분위기에서 500 mL 둥근 바닥 플라스크에 9-브로모-10-(4-나프탈렌-2-일-d7)페닐-2,3,5,6-d4)안트라센-1,2,3,4,5,6,7,8-d8(9-bromo-10-(4-(naphthalen-2-yl-d7)phenyl-2,3,5,6-d4)anthracene-1,2,3,4,5,6,7,8-d8) (6.50 g, 13.60 mmol), 및 화합물 a-3(6.67 g, 14.96 mmol)을 테트라하이드로퓨란 240 mL에 완전히 녹인 후 2M 탄산칼륨수용액(120 mL)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.47 g, 0.41 mmol)을 넣은 후 4시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 톨루엔 260 mL로 재결정하여 화합물 10(6.31 g, 수율: 64%)을 제조하였다. MS[M+H]+= 7239-Bromo-10-(4-naphthalen-2-yl-d7)phenyl-2,3,5,6-d4)anthracene-1,2,3,4,5 in a 500 mL round bottom flask under nitrogen atmosphere. ,6,7,8-d8(9-bromo-10-(4-(naphthalen-2-yl-d7)phenyl-2,3,5,6-d4)anthracene-1,2,3,4,5 ,6,7,8-d8) (6.50 g, 13.60 mmol), and compound a-3 (6.67 g, 14.96 mmol) were completely dissolved in 240 mL of tetrahydrofuran, and then 2M aqueous potassium carbonate solution (120 mL) was added. , tetrakis-(triphenylphosphine)palladium (0.47 g, 0.41 mmol) was added, and then heated and stirred for 4 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 260 mL of toluene to prepare Compound 10 (6.31 g, yield: 64%). MS[M+H] + = 723
<< 제조예Manufacturing example 11> 화합물 11의 화합물 합성 11> Compound synthesis of compound 11
Figure PCTKR2023019646-appb-img-000049
Figure PCTKR2023019646-appb-img-000049
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-브로모-10-(4-(나프탈렌-1-일-d7)페닐-2,3,5,6-d4)안트라센-1,2,3,4,5,6,7,8-d8(9-bromo-10-(4-(naphthalen-1-yl-d7)phenyl-2,3,5,6-d4)anthracene-1,2,3,4,5,6,7,8-d8) (5.50 g, 16.13 mmol), 및 화합물 a-5(8.45 g, 17.74 mmol)을 테트라하이드로퓨란 240 mL에 완전히 녹인 후 2M 탄산칼륨수용액(120 mL)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.56 g, 0.48 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 톨루엔 280 mL로 재결정하여 화합물 11(6.17 g, 수율: 63%)을 제조하였다. MS[M+H]+= 734Compound 9-bromo-10-(4-(naphthalen-1-yl-d7)phenyl-2,3,5,6-d4)anthracene-1,2,3,4 in a 500 mL round bottom flask under nitrogen atmosphere. ,5,6,7,8-d8(9-bromo-10-(4-(naphthalen-1-yl-d7)phenyl-2,3,5,6-d4)anthracene-1,2,3,4 ,5,6,7,8-d8) (5.50 g, 16.13 mmol), and compound a-5 (8.45 g, 17.74 mmol) were completely dissolved in 240 mL of tetrahydrofuran and then added to 2M aqueous potassium carbonate solution (120 mL). After adding tetrakis-(triphenylphosphine)palladium (0.56 g, 0.48 mmol), it was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 280 mL of toluene to prepare Compound 11 (6.17 g, yield: 63%). MS[M+H] + = 734
<< 제조예Manufacturing example 12> 화합물 12의 화합물 합성 12> Compound synthesis of compound 12
Figure PCTKR2023019646-appb-img-000050
Figure PCTKR2023019646-appb-img-000050
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(10-브로모안트라센-9-일-1,2,3,4,5,6,7,8-d8)페난트렌-1,2,3,4,5,6,7,8,10-d9(9-(10-bromoanthracen-9-yl-1,2,3,4,5,6,7,8-d8)phenanthrene-1,2,3,4,5,6,7,8,10-d9)(6.50 g, 14.44 mmol), 및 화합물 a-2(7.09 g, 15.89 mmol)를 테트라하이드로퓨란 240 mL에 완전히 녹인 후 2M 탄산칼륨수용액(120 mL)을 첨가하고, 테트라키스-(트리페닐포스핀)팔라듐(0.50 g, 0.43 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 물 층을 제거하고 무수황산마그네슘으로 건조한 후 감압농축 시키고 톨루엔 260 mL로 재결정하여 화합물 12(6.51 g, 수율: 65%)를 제조하였다. MS[M+H]+= 690Compound 9-(10-bromoanthracen-9-yl-1,2,3,4,5,6,7,8-d8)phenanthrene-1,2,3, in a 500 mL round bottom flask under nitrogen atmosphere. 4,5,6,7,8,10-d9(9-(10-bromoanthracen-9-yl-1,2,3,4,5,6,7,8-d8)phenanthrene-1,2,3 , 4,5,6,7,8,10-d9) (6.50 g, 14.44 mmol), and compound a-2 (7.09 g, 15.89 mmol) were completely dissolved in 240 mL of tetrahydrofuran and then dissolved in 2M potassium carbonate aqueous solution ( 120 mL) was added, tetrakis-(triphenylphosphine)palladium (0.50 g, 0.43 mmol) was added, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the water layer was removed, dried with anhydrous magnesium sulfate, concentrated under reduced pressure, and recrystallized with 260 mL of toluene to prepare Compound 12 (6.51 g, yield: 65%). MS[M+H] + = 690
실시예Example 1-1. 1-1.
ITO(indium tin oxide)가 1,000Å의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때, 세제로는 피셔사(Fischer Co.) 제품을 사용하였으며, 증류수로는 밀러포어사(Millipore Co.) 제품의 필터(Filter)로 2차로 걸러진 증류수를 사용하였다. ITO를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후, 이소프로필알콜, 아세톤, 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한, 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.A glass substrate coated with a thin film of ITO (indium tin oxide) with a thickness of 1,000 Å was placed in distilled water with a detergent dissolved in it and washed ultrasonically. At this time, a detergent manufactured by Fischer Co. was used, and distilled water filtered secondarily using a filter manufactured by Millipore Co. was used as distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing with distilled water, it was ultrasonic washed with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned for 5 minutes using oxygen plasma and then transported to a vacuum evaporator.
이렇게 준비된 양극인 ITO 투명 전극 위에 하기 화합물 HI1 및 하기 화합물 HI2의 화합물을 98:2(몰비)의 비가 되도록 100Å의 두께로 열 진공 증착하여 정공주입층을 형성하였다. 상기 정공주입층 위에 하기 화학식 HT1으로 표시되는 화합물(1150Å)을 진공 증착하여 정공수송층을 형성하였다. 이어서, 상기 정공수송층 위에 막 두께 50Å으로 EB1의 화합물을 진공 증착하여 전자차단층을 형성하였다. 이어서, 상기 전자차단층 위에 막 두께 200Å으로 상기 제조예 1에서 합성한 화합물 1 및 하기 화학식 BD로 표시되는 화합물을 25:1의 중량비로 진공증착하여 발광층을 형성하였다. 상기 발광층 위에 막 두께 50Å으로 HB1의 화합물을 진공 증착하여 정공차단층을 형성하였다. 이어서, 상기 정공차단층 위에 하기 화학식 ET1으로 표시되는 화합물과 하기 화학식 LiQ로 표시되는 화합물을 1:1의 중량비로 진공증착하여 310Å의 두께로 전자 주입 및 수송층을 형성하였다. 상기 전자 주입 및 수송층 위에 순차적으로 12Å두께로 리튬플로라이드(LiF)와 1,000Å 두께로 알루미늄을 증착하여 음극을 형성하였다. On the ITO transparent electrode, which is the anode prepared in this way, the following compounds HI1 and the following compounds HI2 were thermally vacuum deposited to a thickness of 100 Å at a ratio of 98:2 (molar ratio) to form a hole injection layer. A hole transport layer was formed by vacuum depositing a compound (1150 Å) represented by the following chemical formula HT1 on the hole injection layer. Subsequently, an electron blocking layer was formed by vacuum depositing the compound of EB1 with a film thickness of 50 Å on the hole transport layer. Next, Compound 1 synthesized in Preparation Example 1 and the compound represented by the formula BD below were vacuum deposited on the electron blocking layer to a film thickness of 200 Å at a weight ratio of 25:1 to form a light emitting layer. A hole blocking layer was formed by vacuum depositing the compound of HB1 with a film thickness of 50 Å on the light emitting layer. Next, a compound represented by the formula ET1 and a compound represented by the formula LiQ were vacuum deposited on the hole blocking layer at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 310 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) to a thickness of 12 Å and aluminum to a thickness of 1,000 Å on the electron injection and transport layer.
Figure PCTKR2023019646-appb-img-000051
Figure PCTKR2023019646-appb-img-000051
상기의 과정에서 유기물의 증착속도는 0.4Å/sec 내지 0.7Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3Å/sec, 알루미늄은 2Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2x10-7 torr 내지 5x10-6 torr를 유지하여, 유기 발광 소자를 제작하였다.In the above process, the deposition rate of organic matter was maintained at 0.4Å/sec to 0.7Å/sec, the deposition rate of lithium fluoride of the cathode was maintained at 0.3Å/sec, and aluminum was maintained at 2Å/sec, and the vacuum degree during deposition was 2x10. An organic light emitting device was manufactured by maintaining -7 torr to 5x10 -6 torr.
실시예Example 1-2 내지 1-2 to 실시예Example 1-12. 1-12.
상기 실시예 1-1에서 화합물 1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. An organic light emitting device was manufactured in the same manner as Example 1-1, except that the compounds listed in Table 1 below were used instead of Compound 1 in Example 1-1.
비교예Comparative example 1-1 내지 1-8. 1-1 to 1-8.
상기 실시예 1-1에서 화합물 1 대신 하기 표 1에 기재된 화합물을 사용하는 것을 제외하고는, 상기 실시예 1-1과 동일한 방법으로 유기 발광 소자를 제조하였다. 하기 표 1에서 사용한 BH1 내지 BH8의 화합물은 하기와 같다. An organic light emitting device was manufactured in the same manner as Example 1-1, except that the compounds listed in Table 1 below were used instead of Compound 1 in Example 1-1. The compounds BH1 to BH8 used in Table 1 below are as follows.
Figure PCTKR2023019646-appb-img-000052
Figure PCTKR2023019646-appb-img-000052
실험예Experiment example ..
상기 실시예 및 비교예에서 제조한 유기 발광 소자에 전류를 인가하였을 때, 전압, 효율, 색좌표 및 수명을 측정하고 그 결과를 하기 표 1에 나타내었다. T95은 휘도가 초기 휘도(1600 nit)에서 95%로 감소되는데 소요되는 시간을 의미한다.When current was applied to the organic light emitting devices manufactured in the above examples and comparative examples, the voltage, efficiency, color coordinate, and lifespan were measured, and the results are shown in Table 1 below. T95 refers to the time it takes for the luminance to decrease from the initial luminance (1600 nit) to 95%.
화합물
(발광층)compound
(Emitting layer) 		전압
(V
@10mA/cm2)Voltage
(V
@10mA/cm 2 ) 		효율
(cd/A
@10mA/cm2)efficiency
(cd/A
@10mA/cm 2 ) 		색좌표
(x,y)Color coordinates
(x,y) 		T95
(hr)T95
(hr)
실시예 1-1Example 1-1 화합물 1Compound 1 4.444.44 6.526.52 (0.145, 0.046)(0.145, 0.046) 256256
실시예 1-2Example 1-2 화합물 2compound 2 4.464.46 6.536.53 (0.146, 0.046)(0.146, 0.046) 257257
실시예 1-3Example 1-3 화합물 3Compound 3 4.454.45 6.566.56 (0.146, 0.045)(0.146, 0.045) 258258
실시예 1-4Example 1-4 화합물 4Compound 4 4.474.47 6.586.58 (0.145, 0.047)(0.145, 0.047) 263263
실시예 1-5Examples 1-5 화합물 5Compound 5 4.484.48 6.546.54 (0.146, 0.046)(0.146, 0.046) 262262
실시예 1-6Example 1-6 화합물 6Compound 6 4.464.46 6.566.56 (0.145, 0.046)(0.145, 0.046) 264264
실시예 1-7Example 1-7 화합물 7Compound 7 4.494.49 6.596.59 (0.147, 0.045)(0.147, 0.045) 299299
실시예 1-8Examples 1-8 화합물 8Compound 8 4.504.50 6.556.55 (0.146, 0.046)(0.146, 0.046) 288288
실시예 1-9Example 1-9 화합물 9Compound 9 4.444.44 6.486.48 (0.146, 0.046)(0.146, 0.046) 283283
실시예 1-10Examples 1-10 화합물 10Compound 10 4.514.51 6.576.57 (0.145, 0.045)(0.145, 0.045) 284284
실시예 1-11Example 1-11 화합물 11Compound 11 4.444.44 6.526.52 (0.146, 0.046)(0.146, 0.046) 296296
실시예 1-12Examples 1-12 화합물 12Compound 12 4.524.52 6.536.53 (0.145, 0.046)(0.145, 0.046) 285285
비교예 1-1Comparative Example 1-1 BH1BH1 4.864.86 5.975.97 (0.146, 0.045)(0.146, 0.045) 163163
비교예 1-2Comparative Example 1-2 BH2BH2 4.734.73 6.126.12 (0.146, 0.045)(0.146, 0.045) 221221
비교예 1-3Comparative Example 1-3 BH3BH3 5.145.14 5.665.66 (0.146, 0.046)(0.146, 0.046) 8282
비교예 1-4Comparative Example 1-4 BH4BH4 6.286.28 4.384.38 (0.145, 0.045)(0.145, 0.045) 6161
비교예 1-5Comparative Example 1-5 BH5BH5 4.864.86 5.975.97 (0.146, 0.045)(0.146, 0.045) 178178
비교예 1-6Comparative Example 1-6 BH6BH6 4.834.83 6.216.21 (0.146, 0.045)(0.146, 0.045) 191191
비교예 1-7Comparative Example 1-7 BH7BH7 4.874.87 6.186.18 (0.146, 0.046)(0.146, 0.046) 192192
비교예 1-8Comparative Example 1-8 BH8BH8 5.595.59 5.735.73 (0.146, 0.046)(0.146, 0.046) 182182
상기 표 1에 나타난 바와 같이, 본 발명의 화합물을 발광층으로 사용한 유기 발광 소자는, 유기 발광 소자의 효율, 구동 전압 및 안정성 면에서 우수한 특성을 나타내었다.As shown in Table 1, the organic light-emitting device using the compound of the present invention as the light-emitting layer showed excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light-emitting device.
구체적으로, 본원 발명의 화합물을 사용한 유기 발광 소자(실시예 1-1 내지 1-12)는 BH1 내지 BH8의 화합물을 사용하여 제조된 비교예 1-1 내지 1-8의 유기 발광 소자보다 저전압, 고효율 및 장수명의 특성을 나타내었다.Specifically, the organic light-emitting devices using the compounds of the present invention (Examples 1-1 to 1-12) have lower voltage, It exhibited characteristics of high efficiency and long lifespan.
이상을 통해 본 발명의 바람직한 실시예(발광층)에 대하여 설명하였지만, 본 발명은 이에 한정되는 것이 아니고 특허청구범위와 발명의 상세한 설명의 범위 안에서 여러 가지로 변형하여 실시하는 것이 가능하고 이 또한 발명의 범주에 속한다.Although the preferred embodiment (light-emitting layer) of the present invention has been described above, the present invention is not limited thereto, and can be implemented with various modifications within the scope of the claims and the detailed description of the invention, and this is also part of the invention. belongs to the category

Claims (12)

  1. 하기 화학식 1의 화합물:Compound of formula 1:
    [화학식 1][Formula 1]
    Figure PCTKR2023019646-appb-img-000053
    Figure PCTKR2023019646-appb-img-000053
    상기 화학식 1에 있어서, In Formula 1,
    B는 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이고, B is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    R1 내지 R16, R25 및 R26은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며, d는 0 내지 2의 정수이고,R1 to R16, R25 and R26 are the same or different from each other and are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and d is an integer of 0 to 2,
    R21 내지 R24는 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이다. R21 to R24 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.
  2. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 21 내지 23 중 어느 하나로 표시되는 것인 화합물:The method according to claim 1, wherein the formula 1 is a compound represented by any one of the following formulas 21 to 23:
    [화학식 21][Formula 21]
    Figure PCTKR2023019646-appb-img-000054
    Figure PCTKR2023019646-appb-img-000054
    [화학식 22][Formula 22]
    Figure PCTKR2023019646-appb-img-000055
    Figure PCTKR2023019646-appb-img-000055
    [화학식 23][Formula 23]
    Figure PCTKR2023019646-appb-img-000056
    Figure PCTKR2023019646-appb-img-000056
    상기 화학식 21 내지 23에 있어서, 치환기 설명은 상기 화학식 1에서 정의한 바와 같다. In Formulas 21 to 23, descriptions of substituents are as defined in Formula 1 above.
  3. 청구항 2에 있어서, 상기 R21 내지 R24는 수소; 또는 중수소인 것인 화합물. The method according to claim 2, wherein R21 to R24 are hydrogen; Or a compound that is deuterium.
  4. 청구항 2에 있어서, 상기 R25 및 R26은 수소; 또는 중수소인 것인 화합물. The method of claim 2, wherein R25 and R26 are hydrogen; Or a compound that is deuterium.
  5. 청구항 1에 있어서, 상기 B는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 하기 화학식 11의 기인 것인 화합물:The method according to claim 1, wherein B is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a compound having the following formula (11):
    [화학식 11][Formula 11]
    Figure PCTKR2023019646-appb-img-000057
    Figure PCTKR2023019646-appb-img-000057
    상기 화학식 11에 있어서, In Formula 11,
    X는 O 또는 S이고, X is O or S,
    R17은 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로아릴기이며, R17 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
    a 및 b는 각각 0 또는 1이며, c는 0 내지 12의 정수이고,a and b are each 0 or 1, c is an integer from 0 to 12,
    *은 화학식 1에 결합되는 부위이다. * is the site bound to Chemical Formula 1.
  6. 청구항 1에 있어서, 상기 B는 치환 또는 비치환된 페닐기; 치환 또는 비치환된 비페닐기; 치환 또는 비치환된 터페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 트리페닐레닐기; 치환 또는 비치환된 디벤조퓨란기; 치환 또는 비치환된 디벤조티오펜기; 치환 또는 비치환된 나프토벤조퓨란기; 또는 치환 또는 비치환된 나프토벤조티오펜기인 것인 화합물.The method according to claim 1, wherein B is a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted naphthobenzofuran group; Or a compound that is a substituted or unsubstituted naphthobenzothiophene group.
  7. 청구항 1에 있어서, 상기 B는 하기 구조 중 어느 하나 또는 둘 이상이 연결된 구조이고, 하기 구조는 중수소로 치환 또는 비치환되는 것인 화합물:The compound according to claim 1, wherein B is a structure in which one or more of the following structures are connected, and the following structures are substituted or unsubstituted with deuterium:
    Figure PCTKR2023019646-appb-img-000058
    Figure PCTKR2023019646-appb-img-000058
    Figure PCTKR2023019646-appb-img-000059
    Figure PCTKR2023019646-appb-img-000059
    상기 구조에 있어서,
    Figure PCTKR2023019646-appb-img-000060
    는 상기 화학식 1에 결합되는 부분이다.    In the above structure,
    Figure PCTKR2023019646-appb-img-000060
    is a portion bound to Formula 1 above.
  8. 청구항 1에 있어서, 상기 R1 내지 R16은 각각 수소; 또는 중수소인 것인 화합물. The method according to claim 1, wherein R1 to R16 are each hydrogen; Or a compound that is deuterium.
  9. 청구항 1에 있어서, 상기 화합물은 하기 구조들 중에서 선택되는 어느 하나인 것인 화합물:The compound according to claim 1, wherein the compound is any one selected from the following structures:
    Figure PCTKR2023019646-appb-img-000061
    Figure PCTKR2023019646-appb-img-000061
    Figure PCTKR2023019646-appb-img-000062
    Figure PCTKR2023019646-appb-img-000062
    Figure PCTKR2023019646-appb-img-000063
    Figure PCTKR2023019646-appb-img-000063
    Figure PCTKR2023019646-appb-img-000064
    Figure PCTKR2023019646-appb-img-000064
    Figure PCTKR2023019646-appb-img-000065
    Figure PCTKR2023019646-appb-img-000065
    Figure PCTKR2023019646-appb-img-000066
    Figure PCTKR2023019646-appb-img-000066
    Figure PCTKR2023019646-appb-img-000067
    Figure PCTKR2023019646-appb-img-000067
    Figure PCTKR2023019646-appb-img-000068
    Figure PCTKR2023019646-appb-img-000068
    Figure PCTKR2023019646-appb-img-000069
    Figure PCTKR2023019646-appb-img-000069
    Figure PCTKR2023019646-appb-img-000070
    Figure PCTKR2023019646-appb-img-000070
    Figure PCTKR2023019646-appb-img-000071
    Figure PCTKR2023019646-appb-img-000071
    Figure PCTKR2023019646-appb-img-000072
    Figure PCTKR2023019646-appb-img-000072
    Figure PCTKR2023019646-appb-img-000073
    .
    Figure PCTKR2023019646-appb-img-000073
    .
  10. 애노드;anode;
    캐소드; 및cathode; and
    상기 애노드와 상기 캐소드 사이에 구비된 1층 이상의 유기물층을 포함하고, Comprising one or more organic layers provided between the anode and the cathode,
    상기 유기물층 중 1층 이상은 청구항 1 내지 9 중 어느 한 항에 따른 화합물을 포함하는 것인 유기 발광 소자. An organic light-emitting device wherein at least one of the organic layers includes the compound according to any one of claims 1 to 9.
  11. 청구항 10에 있어서, 상기 화합물을 포함하는 유기물층은 발광층인 것인 유기 발광 소자. The organic light-emitting device of claim 10, wherein the organic material layer containing the compound is a light-emitting layer.
  12. 청구항 11에 있어서, 상기 발광층은 하기 화학식 D의 화합물을 더 포함하는 것인 유기 발광 소자. The organic light-emitting device according to claim 11, wherein the light-emitting layer further includes a compound of formula D below.
    [화학식 D][Formula D]
    Figure PCTKR2023019646-appb-img-000074
    Figure PCTKR2023019646-appb-img-000074
    상기 화학식 D에 있어서,In Formula D,
    X1 및 X2는 서로 같거나 상이하고, 각각 독립적으로 CR'; 또는 NR"이고, X1 및 X2 중 적어도 하나는 NR"이며, X1 and X2 are the same or different from each other and are each independently CR'; or NR", and at least one of X1 and X2 is NR",
    R401 내지 R403, R' 및 R"은 서로 같거나 상이하고, 각각 독립적으로 수소; 중수소; 할로겐기; 니트릴기; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 시클로알킬기; 치환 또는 비치환된 알콕시기; 치환 또는 비치환된 아릴옥시기; 치환 또는 비치환된 실릴기; 치환 또는 비치환된 아민기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접한 기와 서로 결합하여, 치환 또는 비치환된 고리를 형성하고,R401 to R403, R' and R" are the same or different from each other, and are each independently hydrogen; deuterium; halogen group; nitrile group; substituted or unsubstituted alkyl group; substituted or unsubstituted cycloalkyl group; substituted or unsubstituted alkoxy A substituted or unsubstituted silyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group; Thus, forming a substituted or unsubstituted ring,
    r401 및 r403은 각각 0 내지 4의 정수이고, r402는 0 내지 3의 정수이고, r401 내지 r403이 각각 2 이상인 경우 괄호 내의 치환기는 서로 같거나 상이하다.r401 and r403 are each an integer from 0 to 4, r402 is an integer from 0 to 3, and when r401 to r403 are each 2 or more, the substituents in the parentheses are the same or different from each other.
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