WO2023027327A1 - Compound and organic light-emitting device comprising same - Google Patents

Compound and organic light-emitting device comprising same Download PDF

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WO2023027327A1
WO2023027327A1 PCT/KR2022/009772 KR2022009772W WO2023027327A1 WO 2023027327 A1 WO2023027327 A1 WO 2023027327A1 KR 2022009772 W KR2022009772 W KR 2022009772W WO 2023027327 A1 WO2023027327 A1 WO 2023027327A1
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compound
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French (fr)
Korean (ko)
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차용범
문현진
이성재
이형진
조우진
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주식회사 엘지화학
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Publication of WO2023027327A1 publication Critical patent/WO2023027327A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D409/12—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 chain containing hetero atoms as chain links
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K99/00—Subject matter not provided for in other groups of this subclass

Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light emitting device, and may include, 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 are injected into the organic material layer, and when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.
  • Patent Document 1 Korean Patent Publication No. 10-2011-0084798
  • An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.
  • L1 and L2 are the same as or different from each other, and are each independently a direct bond; An arylene group consisting of a monocycle; Or a bicyclic arylene group,
  • Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic aryl group; a bicyclic aryl group; And one selected from the group consisting of a heterocyclic group, or a group in which two or more groups selected from the group are connected,
  • R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bonded to adjacent groups to form a substituted or unsubstituted ring;
  • R2 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • a is an integer from 0 to 8, and when a is 2 or more, 2 or more R1s are the same as or different from each other.
  • an exemplary embodiment of the present specification is an anode; cathode; and one or more organic material layers provided between the anode and the cathode, wherein at least one of the organic material layers includes the compound represented by Chemical Formula 1.
  • the compounds described in this specification can be used as a material for an organic material layer of an organic light emitting device.
  • the compound according to at least one exemplary embodiment of the present specification may improve efficiency, low driving voltage, and/or lifetime characteristics of an organic light emitting device.
  • the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron blocking, luminescence, hole blocking, electron transport, or electron injection materials.
  • FIG. 1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 6, and a cathode 10 are sequentially stacked.
  • FIG. 2 shows a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, and an electron transport layer 8 , shows an example of an organic light emitting device in which an electron injection layer 9 and a cathode 10 are sequentially stacked.
  • Figure 3 is a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), electron transport and injection layer 11 and a cathode 10 are sequentially stacked.
  • substitution means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position to be substituted is not limited as long as the hydrogen atom is substituted, that is, a position where the substituent is substituted, and when two or more are substituted , Two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted means deuterium; halogen group; nitrile group (-CN); nitro group; hydroxy group; an alkyl group; cycloalkyl group; alkoxy group; phosphine oxide group; aryloxy group; Alkyl thioxy group; Arylthioxy group; an alkyl sulfoxy group; aryl sulfoxy group; alkenyl group; silyl group; boron group; amine group; aryl group; Or substituted with one or two or more substituents selected from the group consisting of heterocyclic groups, or substituted with substituents in which two or more substituents among the above exemplified substituents are connected, or without any substituents.
  • a substituent in which two or more substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.
  • substituted or unsubstituted means deuterium; halogen group; nitrile group; nitro group; hydroxy group; amino group; silyl group; boron group; alkoxy group; aryloxy group; an alkyl group; cycloalkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or is substituted with a substituent in which two or more substituents from among the above exemplified substituents are connected, or does not have any substituents.
  • substituted or unsubstituted means deuterium; halogen group; nitrile group; an alkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or is substituted with a substituent in which two or more substituents from among the above exemplified substituents are connected, or does not have any substituents.
  • examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).
  • the silyl group may be represented by a chemical formula of -SiY a Y b Y c , wherein Y a , Y b and Y c are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but is not limited thereto. don't
  • the boron group may be represented by the chemical formula -BY d Y e , wherein Y d and Y e are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, but is not limited thereto.
  • the alkyl group may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10.
  • alkyl group examples 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 is not limited thereto.
  • the alkoxy group may be straight chain, branched chain or cyclic chain.
  • the number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms.
  • Alkyl groups, alkoxy groups, and substituents containing other alkyl moieties described herein include both straight-chain and branched forms.
  • the alkenyl group may be linear 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 exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styrenyl group, etc., but is not limited thereto.
  • the alkynyl group is a substituent including a triple bond between carbon atoms and may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkynyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkynyl group is 2 to 10.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but are not limited thereto.
  • the amine group is -NH 2
  • the amine group may be substituted with the aforementioned 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 group examples include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, diphenylamine group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, A ditolylamine group, a phenyltolylamine group, a diphenylamine group, and the like, but are not limited thereto.
  • 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 number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, etc. as a monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenylenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is limited thereto it is not going to be
  • the aryl group may be a monocyclic aryl group or a polycyclic aryl group (two or more ring aryl groups).
  • An aryl group consisting of a monocyclic ring may be a phenyl group; Or it may mean a group in which two or more phenyl groups are connected.
  • the monocyclic aryl group may include, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like.
  • the polycyclic aryl group may mean a group in which two or more monocyclic rings are condensed, such as a naphthyl group and a phenanthrenyl group.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto. .
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.
  • fluorenyl group When the fluorenyl group is substituted, , , spirofluorenyl groups such as; (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.
  • aryl group in the aryloxy group may be applied to the above description of the aryl group.
  • the description of the alkyl group described above may be applied to the alkyl group in the alkylthioxy group and the alkylsulfoxy group.
  • the description of the aryl group described above may be applied to the aryl group among the arylthiooxy group and the arylsulfoxy group.
  • the heterocyclic group is a ring 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 preferably has 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 group examples include a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, carba A sol group, a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, an indenocarbazole group, a triazinyl group, and the like, but are not limited thereto.
  • heterocyclic group described above may be applied except that the heteroaryl group is aromatic.
  • the description of the aryl group may be applied except that the arylene group is divalent.
  • heterocyclic group may be applied except that the divalent heterocyclic ring is divalent.
  • ring refers to a hydrocarbon ring; or a heterocyclic ring.
  • the hydrocarbon ring may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or the aryl group.
  • the meaning of forming a ring by bonding with adjacent groups means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; A substituted or unsubstituted aromatic heterocycle; or to form a condensed ring thereof.
  • the hydrocarbon ring means a ring composed of only carbon and hydrogen atoms.
  • the heterocycle refers to a ring containing at least one selected from elements such as 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 is a non-aromatic ring and refers to a ring composed of only carbon and hydrogen atoms.
  • Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc. Not limited to this.
  • an aromatic hydrocarbon ring means an aromatic ring composed of only 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 and the like, but are not limited thereto.
  • an aromatic hydrocarbon ring may be interpreted as the same meaning as an aryl group.
  • an aliphatic heterocycle means an aliphatic ring containing one or more of heteroatoms.
  • aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine , Thiocane, etc., but are not limited thereto.
  • an aromatic heterocycle means an aromatic ring containing one or more of heteroatoms.
  • aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parasol, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thia Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine , phenanthridine, diazanaphthalene, driazainden, indole, indolizine, benzothiazole, benzooxazole, benzoimid
  • Formula 1 of the present invention has a meta-biphenylene linker of a specific structure between the carbazole group and the amine group, includes an additional substituent R2 to the phenylene group directly bonded to the amine group in the biphenylene group, and the amine group is an aryl composed of a monocyclic ring. It is characterized by including a group, a bicyclic aryl group or a heterocyclic group.
  • an organic light emitting device having high efficiency, low voltage and/or long lifespan characteristics can be obtained.
  • the voltage of the device tends to be high and the efficiency to be low because the tricyclic or more ring aryl group is relatively larger than the monocyclic or bicyclic aryl group.
  • the thermal stability is low, since the purity tends to decrease during sublimation, there is a problem in that life characteristics are also deteriorated.
  • L1 and L2 are the same as or different from each other, and are each independently a direct bond; An arylene group consisting of a monocycle; Or a bicyclic arylene group,
  • Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic aryl group; a bicyclic aryl group; And one selected from the group consisting of a heterocyclic group, or a group in which two or more groups selected from the group are connected,
  • R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bonded to adjacent groups to form a substituted or unsubstituted ring;
  • R2 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • a is an integer from 0 to 8, and when a is 2 or more, 2 or more R1s are the same as or different from each other.
  • L1 and L2 are the same as or different from each other, and are each independently a direct bond; An arylene group consisting of a monocycle; or a bicyclic arylene group.
  • L1 and L2 are the same as or different from each other, and are each independently a direct bond; A monocyclic arylene group having 6 to 60 carbon atoms; or a bicyclic arylene group.
  • L1 and L2 are the same as or different from each other, and are each independently a direct bond; A monocyclic arylene group having 6 to 30 carbon atoms; or a bicyclic arylene group.
  • L1 and L2 are the same as or different from each other, and are each independently a direct bond; or a monocyclic or bicyclic arylene group having 6 to 30 carbon atoms.
  • L1 and L2 are the same as or different from each other, and are each independently a direct bond; phenylene group; biphenylene group; Terphenylene group; or a naphthylene group.
  • L1 and L2 are the same as or different from each other, and are each independently a direct bond; phenylene group; biphenylene group; or a naphthylene group.
  • L1 and L2 are the same as or different from each other, and each independently represents a direct bond or one of the following structural formulas.
  • the dotted line means the binding position
  • Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic aryl group; a bicyclic aryl group; And one selected from the group consisting of a heterocyclic group, or a group in which two or more groups selected from the above group are connected.
  • Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic aryl group having 6 to 60 carbon atoms; a bicyclic aryl group; And one selected from the group consisting of a heterocyclic group having 2 to 60 carbon atoms, or a group in which two or more groups selected from the above group are connected.
  • Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic aryl group having 6 to 30 carbon atoms; a bicyclic aryl group; and a heterocyclic group having 2 to 30 carbon atoms, or a group in which two or more groups selected from the group are connected.
  • Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic aryl group having 6 to 30 carbon atoms; a bicyclic aryl group; and a group consisting of O or S-containing heterocyclic groups having 2 to 30 carbon atoms, or a group in which two or more groups selected from the above group are connected.
  • Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic aryl group having 6 to 30 carbon atoms; a bicyclic aryl group; And one selected from the group consisting of O or S-containing heterocyclic groups having 2 to 30 carbon atoms, or a monocyclic aryl group having 6 to 30 carbon atoms; and a group in which two or more groups selected from the group consisting of bicyclic aryl groups are connected.
  • Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic aryl group or a phenyl group unsubstituted or substituted with a bicyclic aryl group; A biphenyl group unsubstituted or substituted with a monocyclic aryl group or a bicyclic aryl group; A terphenyl group unsubstituted or substituted with a monocyclic aryl group or a bicyclic aryl group; a quarterphenyl group unsubstituted or substituted with a monocyclic aryl group or a bicyclic aryl group; a naphthyl group unsubstituted or substituted with a monocyclic aryl group or a bicyclic aryl group; a dibenzofuran group unsubstituted or substituted with a monocyclic aryl group or a bicyclic aryl group; or a dibenzofuran group unsubsti
  • Ar1 and Ar2 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group; A phenyl group, a biphenyl group, a terphenyl group, or a substituted or unsubstituted biphenyl group with a naphthyl group; A terphenyl group unsubstituted or substituted with a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group; Quarterphenyl group unsubstituted or substituted with a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group; a naphthyl group unsubstituted or substituted with a phenyl group, a biphen
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a naphthyl group; A biphenyl group unsubstituted or substituted with a naphthyl group; terphenyl group; Quarter phenyl group; a naphthyl group unsubstituted or substituted with a phenyl group or a biphenyl group; Dibenzofuran group; or a dibenzothiophene group.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently represented by any one of the following structural formulas.
  • the dotted line means the binding position
  • At least one of Ar1 and Ar2 is a monocyclic aryl group; and a bicyclic aryl group, or a group in which two or more groups selected from the group are connected.
  • At least one of Ar1 and Ar2 is a monocyclic aryl group; and a bicyclic aryl group, or a group in which two or more groups selected from the group are connected.
  • At least one of Ar1 and Ar2 is a heterocyclic group.
  • R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or bonded to adjacent groups to form a substituted or unsubstituted ring.
  • R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or bonded to an adjacent group to form a substituted or unsubstituted ring having 2 to 60 carbon atoms.
  • R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or bonded to an adjacent group to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.
  • R1 is hydrogen; heavy hydrogen; an alkyl group having 1 to 20 carbon atoms; an aryl group having 6 to 30 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms, or bonded to an adjacent group to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • R1 is hydrogen; Or deuterium, or bonded to adjacent groups to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms.
  • R1 is hydrogen; Or deuterium, or bonded to adjacent groups to form a benzene ring.
  • R1 is hydrogen; or deuterium.
  • R1 is hydrogen
  • R2 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • R2 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • R2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • R2 is an aryl group having 6 to 30 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms.
  • R2 is an aryl group having 6 to 30 carbon atoms; or a heterocyclic group containing O or S of 2 to 30 carbon atoms.
  • R2 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.
  • R2 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.
  • R2 is a phenyl group; biphenyl group; naphthyl group; phenanthrenyl group; Dibenzofuran group; or a dibenzothiophene group.
  • R2 is a phenyl group; biphenyl group; naphthyl group; phenanthrenyl group; or a dibenzofuran group.
  • R2 is represented by any one of the following structural formulas.
  • the dotted line means the binding position
  • R2 is represented by any one of the following structural formulas.
  • the dotted line means the binding position
  • a is an integer from 0 to 8.
  • a is 0.
  • a is 1.
  • a is 8.
  • Formula 1 is represented by any one of Formulas 1-1 to 1-5 below.
  • X is O; or S.
  • X is O.
  • X is S.
  • Chemical Formula 1 is represented by any one of Chemical Formulas 1-1 and 2-1 to 2-9.
  • X is O; or S.
  • Formula 1 is represented by any one of the following compounds.
  • a compound represented by Formula 1 may have a core structure as shown in Reaction Scheme 1 below. Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.
  • compounds having various energy band gaps may be synthesized by introducing various substituents into the core structure of the compound represented by Formula 1.
  • the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents into the core structure of the above structure.
  • the present specification provides an organic light emitting device including the aforementioned compound.
  • An organic light emitting device includes an anode; cathode; and one or more organic material layers provided between the anode and the cathode, wherein at least one of the organic material layers includes a compound represented by Formula 1 above.
  • the organic light emitting device of the present specification may be manufactured by a conventional organic light emitting device manufacturing method and material, except for forming an organic material layer using the compound of Formula 1 described above.
  • the compound may be formed as 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 coating method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
  • the organic material layer of the organic light emitting device of the present specification may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention includes at least one of a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as an organic material layer.
  • the structure of the organic light emitting device of the present specification is not limited thereto and may include fewer or more organic material layers.
  • the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer comprises a compound represented by the above-described formula (1).
  • the hole injection layer, the hole transport layer, or the hole injection and transport layer comprises a compound represented by the above-described formula (1).
  • the organic material layer may include a hole transport layer or a hole injection layer, and the hole transport layer or hole injection layer may include the compound represented by Chemical Formula 1.
  • the organic material layer includes an electron blocking layer
  • the electron blocking layer includes the compound represented by Chemical Formula 1.
  • the organic material layer includes an electron injection layer, an electron transport layer, an electron transport and injection layer, or a hole blocking layer, and the electron injection layer, the electron transport layer, the electron transport and injection layer, or the hole blocking layer It may include the compound represented by Formula 1 above.
  • the organic material layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer, and the electron transport layer, the electron injection layer, or the electron transport and injection layer is represented by the above-described formula (1) compounds may be included.
  • the organic material layer may include an electron control layer, and the electron control layer may include the compound represented by Formula 1 described above.
  • the organic material layer includes a hole blocking layer
  • the hole blocking layer includes the compound represented by Chemical Formula 1.
  • the organic material layer is an electron transport and injection layer
  • the electron transport and injection layer includes the compound represented by Formula 1 above.
  • the thickness of the organic material layer including the compound of Formula 1 may be 5 ⁇ to 2000 ⁇ , 5 ⁇ to 500 ⁇ , and preferably 10 ⁇ to 200 ⁇ .
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 above.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 as a host.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 as a dopant.
  • the organic material layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Chemical Formula 1 described above.
  • the light emitting layer further includes a fluorescent dopant or a phosphorescent dopant.
  • the dopant in the light emitting layer is included in 1 part by weight to 50 parts by weight based on 100 parts by weight of the host.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the compound represented by Chemical Formula 1 as a host and may further include an additional host.
  • the dopant includes an arylamine-based compound, a heterocyclic compound including boron and nitrogen, or an Ir complex.
  • the organic light emitting device of the present specification may further include one or more organic material layers of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole injection and transport layer. there is.
  • the organic light emitting device includes an anode; cathode; and two or more organic material layers provided between the anode and the cathode, wherein at least one of the two or more organic material layers includes the compound represented by Chemical Formula 1.
  • the two or more organic material layers may be two or more selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a hole transport and injection layer, and an electron blocking layer.
  • the two or more organic material layers may be two or more selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron control layer, and a hole blocking layer.
  • the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound represented by Chemical Formula 1.
  • the compound represented by Formula 1 may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
  • materials other than the compound represented by Formula 1 may be the same as or different from each other.
  • the organic material layer containing the compound represented by Formula 1 is an electron transport layer, an electron injection layer, or an electron transport and injection layer
  • the electron transport layer, the electron injection layer, or the electron transport and injection layer is an n-type dopant or an organometallic compound.
  • the n-type dopant or organometallic compound those known in the art may be used, and for example, a metal or a metal complex may be used.
  • the n-type dopant or organometallic compound may be LiQ, but is not limited thereto.
  • the electron transport layer, the electron injection layer, or the electron transport and injection layer including the compound represented by Formula 1 may further include lithium quinolate (LiQ).
  • the compound represented by Chemical Formula 1 and the n-type dopant or organometallic compound may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4. According to one example, the compound represented by Chemical Formula 1 and the n-type dopant or organometallic compound may be included in a weight ratio of 1:1.
  • the organic material layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes the compound represented by Chemical Formula 1.
  • the compound represented by Chemical Formula 1 may be included in one of the two or more hole transport layers, and may be included in each of the two or more hole transport layers.
  • materials other than the compound represented by Formula 1 may be the same or different from each other. there is.
  • the organic material layer further includes a hole injection layer or a hole transport layer containing a compound containing an arylamine group, a carbazolyl group, or a benzocarbazolyl group in addition to the organic material layer containing the compound represented by Formula 1 can include
  • the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • the organic material layer may include an electron blocking layer, and materials known in the art may be used for the electron blocking layer.
  • the organic light emitting device may have, for example, a stacked structure as described below, but is not limited thereto.
  • the structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1 to 3 , but is not limited thereto.
  • FIG. 1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 6, and a cathode 10 are sequentially stacked.
  • the compound may be included in the light emitting layer (6).
  • the compound is a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light emitting layer (6), a hole blocking layer (7), an electron transport layer (8) or an electron injection layer. (9) can be included.
  • Figure 3 is a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), electron transport and injection layer 11 and a cathode 10 are sequentially stacked.
  • the compound is applied to the hole injection layer 3, the hole transport layer 4, the electron blocking layer 5, the light emitting layer 6, the hole blocking layer 7 or the electron transport and injection layer 11. can be included
  • the electron blocking layer and the light emitting layer may be provided adjacently.
  • the electron blocking layer and the light emitting layer may be provided in physical contact with each other.
  • the hole transport layer and the electron blocking layer may be provided adjacent to each other.
  • the hole transport layer and the electron blocking layer may be provided in physical contact with each other.
  • the organic light emitting device of the present specification may be manufactured with materials and methods known in the art, except that at least one layer of organic material layers includes the compound, that is, the compound represented by Chemical Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device uses a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal or conductive metal oxide or an alloy thereof on a substrate. It is prepared by depositing an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer thereon, and then depositing a material that can be used as a cathode thereon. It can be.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer may further include at least one of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole injection and transport layer.
  • the organic material layer may have a multilayer structure including a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, and an electron transport and injection layer, but is not limited thereto and may have a single layer structure.
  • the organic material layer can be formed by a solvent process other than a deposition method using various polymer materials, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or a thermal transfer method. Can be made in layers.
  • the anode is an electrode for injecting holes
  • the anode material is preferably a material having a high work function so that holes can be smoothly injected into the organic material layer.
  • Specific examples of the anode material 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; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the cathode is an electrode for injecting electrons
  • the cathode material is a material having a small work function so as to easily inject electrons into the organic material layer.
  • Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
  • the hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer
  • the hole injection material is a material that can receive holes well from the anode at a low voltage, HOMO (highest occupied) of the hole injection material molecular orbital) is preferably between the work function of the anode material and the HOMO of the surrounding organic layer.
  • HOMO highest occupied
  • the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials.
  • the hole injection layer may have a thickness of 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 the thickness is 150 nm or less, the thickness of the hole injection layer is too thick, so that a driving voltage is required to improve hole movement. There are advantages to preventing it from rising.
  • the hole injection layer may include an arylamine compound including a carbazole group and a p-type dopant.
  • the amine compound is represented as Het101-L101-N(Ar101)(Ar102), Het101 is a substituted or unsubstituted carbazole group, L101 is a direct bond or a substituted or unsubstituted arylene group, Ar101 and Ar102 are the same as or different from each other, and each independently may be a substituted or unsubstituted aryl group.
  • the amine compound and the p-type dopant may be included in an appropriate molar ratio, and according to one example, the amine compound and the p-type dopant may be included in a molar ratio of 99.9:0.1 to 90:10.
  • the hole transport layer may play a role of facilitating hole transport.
  • a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer and a material having high hole mobility is suitable.
  • Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.
  • the hole transport layer may include an arylamine compound including a carbazole group.
  • a hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
  • the above-mentioned compounds or materials known in the art may be used for the electron blocking layer.
  • the electron blocking layer may include a compound represented by Formula 1 of the present invention.
  • 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 ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; Polyfluorene, rubrene, etc., but are not limited thereto.
  • Alq 3 8-hydroxy-quinoline aluminum complex
  • carbazole-based compounds dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compounds
  • compounds of the benzoxazole, benzthiazole and benzimidazole series compounds of the benzoxazole, benzthiazole and benzimidazole series
  • PV poly(p-phenylenevinylene)-based polymers
  • spiro compounds Polyfluorene, rubrene, etc., but are not limited there
  • a host material for the light emitting layer includes a condensed aromatic ring derivative or a compound containing a hetero ring.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.
  • PIQIr (acac) bis (1-phenylisoquinoline) acetylacetonateiridium
  • PQIr (acac) bis (1-phenylquinoline) acetylacetonate iridium
  • PQIr (tris (1-phenylquinoline) iridium) are used as light emitting dopants.
  • a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum), but is not limited thereto.
  • a phosphorescent material such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the light emitting dopant.
  • a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum)
  • Alq3 tris(8-hydroxyquinolino)aluminum
  • a phosphorescent material such as (4,6-F2ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distryarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited thereto.
  • the light emitting layer may include an anthracene compound substituted with an aryl group or a heterocyclic group as a host and a pyrene compound substituted with an amine group as a dopant.
  • the anthracene compound may have a structure in which carbon 9 and carbon 10 are substituted with an aryl group or a heterocyclic group.
  • the host and the dopant may be included in an appropriate weight ratio, and according to one example, the host and the dopant may be included in a weight ratio of 100:1 to 100:10.
  • a hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.
  • the hole blocking layer may include a compound including an N-containing heterocyclic group and a fluorene ring.
  • the electron transport layer may serve to facilitate electron transport.
  • the electron transport material a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Specific examples include Al complexes of the aforementioned compounds or 8-hydroxyquinoline; Complexes containing Alq 3 ; organic radical compounds; hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer may have a thickness of 1 nm to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing deterioration in electron transport properties, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the increase in driving voltage to improve electron movement. There are benefits to avoiding it.
  • the electron transport layer may include a compound containing two N-containing heterocyclic groups, and may further include an n-type dopant or an organometallic compound.
  • the n-type dopant or organometallic compound may be LiQ
  • the compound containing two N-containing heterocyclic groups and the n-type dopant (or organometallic compound) have a ratio of 2:8 to 8:2, For example, it may be included in a weight ratio of 4:6 to 6:4.
  • the electron injection layer may serve to smoothly inject electrons.
  • the electron injecting material has the ability to transport electrons, has an excellent electron injecting 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 also , compounds having excellent thin film forming ability are preferred.
  • Examples of the metal complex compound 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)( There are o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. Not limited to this.
  • the hole blocking layer is a layer that blocks holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.
  • the organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a double side emission type depending on the material used.
  • the organic light emitting device may be included in and used in various electronic devices.
  • the electronic device may be a display panel, a touch panel, a solar module, a lighting device, and the like, but is not limited thereto.
  • a glass substrate coated with ITO (indium tin oxide) to a thickness of 1,000 ⁇ was put in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • a Fischer Co. product was used as the detergent, and distilled water filtered through a second filter of a Millipore Co. product was used as the distilled water.
  • ultrasonic cleaning was performed twice with distilled water for 10 minutes.
  • ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner.
  • solvents such as isopropyl alcohol, acetone, and methanol
  • a hole injection layer was formed by thermally vacuum-depositing the following compound HI1 and the following compound HI2 to a thickness of 100 ⁇ in a ratio of 98:2 (molar ratio) on the ITO transparent electrode prepared as described above.
  • a hole transport layer was formed by vacuum depositing a compound (1150 ⁇ ) represented by Chemical Formula HT1 on the hole injection layer. Then, the compound 1 prepared in Preparation Example 1 was vacuum deposited to form a film thickness of 50 ⁇ on the hole transport layer to form an electron blocking layer. Subsequently, a light emitting layer was formed by vacuum depositing a compound represented by Chemical Formula BH and a compound represented by Chemical Formula BD at a weight ratio of 25:1 to a film thickness of 200 ⁇ on the electron blocking layer.
  • a hole blocking layer was formed on the light emitting layer by vacuum depositing a compound represented by Chemical Formula HB1 to a film thickness of 50 ⁇ . Subsequently, a compound represented by Chemical Formula ET1 and a compound represented by Chemical Formula LiQ were vacuum deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 310 ⁇ .
  • a negative electrode 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.
  • the deposition rate of the organic material was maintained at 0.4 to 0.7 ⁇ /sec
  • the deposition rate of lithium fluoride on the negative electrode was 0.3 ⁇ /sec
  • the deposition rate of aluminum was 2 ⁇ /sec
  • the vacuum level during deposition was 2 ⁇ 10 Maintaining -7 to 5 ⁇ 10 -6 torr, an organic light emitting device was fabricated.
  • An organic light emitting device was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1.
  • An organic light emitting device was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1.
  • the compounds of EB2, EB3, EB4 and EB5 used in Table 1 are as follows.
  • T95 means the time required 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 an electron blocking layer exhibited excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device.
  • Examples 1-1 to 1-15 it can be seen that when a material in which an additional substituent R2 is bonded to an amine-linked phenylene group among meta-biphenylene groups is used as an electron blocking layer, it exhibits characteristics of low voltage, high efficiency, and long lifespan. there was.
  • Comparative Example Compound EB1 comprising a linker having a structure different from the meta-biphenylene group of the present invention or having an amine group substituted with a phenanthrenyl group or fluorenyl group, which is a tricyclic aryl group.
  • the voltage increased, the efficiency decreased, and in particular, the stability (lifetime) was greatly reduced.

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Abstract

The present specification provides a compound represented by chemical formula 1, and an organic light-emitting device comprising the compound.

Description

화합물 및 이를 포함하는 유기 발광 소자Compound and organic light emitting device including the same
본 출원은 2021년 8월 23일에 한국특허청에 제출된 한국 특허 출원 제10-2021-0110793호의 출원일의 이익을 주장하며, 그 내용 전부는 본 명세서에 포함된다.This application claims the benefit of the filing date of Korean Patent Application No. 10-2021-0110793 filed with the Korean Intellectual Property Office on August 23, 2021, all of which are incorporated herein.
본 명세서는 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.The present specification relates to a compound and an organic light emitting device including 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, the organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material. An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often composed of a multi-layer structure composed of different materials to increase the efficiency and stability of the organic light emitting device, and may include, 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 are injected into the organic material layer, and when the injected holes and electrons meet, excitons are formed. When it falls back to the ground state, it glows.
상기와 같은 유기 발광 소자를 위한 새로운 재료의 개발이 계속 요구되고 있다.Development of new materials for the organic light emitting device as described above has been continuously demanded.
[선행기술문헌][Prior art literature]
(특허문헌 1) 한국 특허공개공보 제10-2011-0084798호(Patent Document 1) Korean Patent Publication No. 10-2011-0084798
본 명세서에서는 화합물 및 이를 포함하는 유기 발광 소자를 제공한다. In the present specification, a compound and an organic light emitting device including the same are provided.
본 명세서의 일 실시상태는 하기 화학식 1로 표시되는 화합물을 제공한다.An exemplary embodiment of the present specification provides a compound represented by Formula 1 below.
[화학식 1][Formula 1]
Figure PCTKR2022009772-appb-img-000001
Figure PCTKR2022009772-appb-img-000001
상기 화학식 1에 있어서,In Formula 1,
L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 단환으로 이루어진 아릴렌기; 또는 2환의 아릴렌기이고,L1 and L2 are the same as or different from each other, and are each independently a direct bond; An arylene group consisting of a monocycle; Or a bicyclic arylene group,
Ar1 및 Ar2은 서로 같거나 상이하고, 각각 독립적으로 단환으로 이루어진 아릴기; 2환의 아릴기; 및 헤테로고리기로 이루어진 군에서 선택된 하나이거나, 상기 군에서 선택된 2 이상의 기가 연결된 기이고,Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic aryl group; a bicyclic aryl group; And one selected from the group consisting of a heterocyclic group, or a group in which two or more groups selected from the group are connected,
R1은 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bonded to adjacent groups to form a substituted or unsubstituted ring;
R2는 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,R2 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
a는 0 내지 8의 정수이고, a가 2 이상인 경우, 2 이상의 R1은 서로 같거나 상이하다.a is an integer from 0 to 8, and when a is 2 or more, 2 or more R1s are the same as or different from each other.
또한, 본 명세서의 일 실시상태는 애노드; 캐소드; 및 상기 애노드와 상기 캐소드 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는 것인 유기 발광 소자를 제공한다.In addition, an exemplary embodiment of the present specification is an anode; cathode; and one or more organic material layers provided between the anode and the cathode, wherein at least one of the organic material layers includes the compound represented by Chemical Formula 1.
본 명세서에 기재된 화합물은 유기 발광 소자의 유기물층의 재료로서 사용될 수 있다. 본 명세서의 적어도 하나의 실시상태에 따른 화합물은 유기 발광 소자에서 효율의 향상, 낮은 구동전압 및/또는 수명 특성을 향상시킬 수 있다. 특히, 본 명세서에 기재된 화합물은 정공주입, 정공수송, 정공주입과 정공수송, 전자차단, 발광, 정공차단, 전자수송, 또는 전자주입 재료로 사용될 수 있다. 또한, 기존 유기 발광 소자에 비하여, 낮은 구동전압, 고효율 및/또는 장수명의 효과가 있다.The compounds described in this specification can be used as a material for an organic material layer of an organic light emitting device. The compound according to at least one exemplary embodiment of the present specification may improve efficiency, low driving voltage, and/or lifetime characteristics of an organic light emitting device. In particular, the compounds described herein can be used as hole injection, hole transport, hole injection and hole transport, electron blocking, luminescence, hole blocking, electron transport, or electron injection materials. In addition, compared to conventional organic light emitting devices, there are effects of low driving voltage, high efficiency, and/or long lifespan.
도 1은 기판(1), 애노드(2), 발광층(6) 및 캐소드(10)가 순차적으로 적층된 유기 발광 소자의 예를 도시한 것이다.1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 6, and a cathode 10 are sequentially stacked.
도 2는 기판(1), 애노드(2), 정공주입층(3), 정공수송층(4), 전자차단층(5), 발광층(6), 정공차단층(7), 전자수송층(8), 전자주입층(9) 및 캐소드(10)가 순차적으로 적층된 유기 발광 소자의 예를 도시한 것이다.2 shows a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, and an electron transport layer 8 , shows an example of an organic light emitting device in which an electron injection layer 9 and a cathode 10 are sequentially stacked.
도 3은 기판(1), 애노드(2), 정공주입층(3), 정공수송층(4), 전자차단층(5), 발광층(6), 정공차단층(7), 전자수송 및 주입층(11) 및 캐소드(10)가 순차적으로 적층된 유기 발광 소자의 예를 도시한 것이다.Figure 3 is a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), electron transport and injection layer 11 and a cathode 10 are sequentially stacked.
[부호의 설명][Description of code]
1: 기판1: substrate
2: 애노드2: anode
3: 정공주입층3: hole injection layer
4: 정공수송층4: hole transport layer
5: 전자차단층5: electron blocking layer
6: 발광층6: light emitting layer
7: 정공차단층7: hole blocking layer
8: 전자수송층8: electron transport layer
9: 전자주입층9: electron injection layer
10: 캐소드10: cathode
11: 전자수송 및 주입층11: electron transport and injection layer
이하 본 명세서에 대하여 더욱 상세히 설명한다. Hereinafter, the present 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 the present specification, when a certain component is said to "include", it means that it may further include other components without excluding other components unless otherwise stated.
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, "
Figure PCTKR2022009772-appb-img-000002
" 또는 점선은 화학식 또는 화합물에 결합되는 위치를 의미한다.In this specification, "
Figure PCTKR2022009772-appb-img-000002
" or the dotted line means the position of bonding to the chemical formula or compound.
본 명세서에서 치환기의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다.Examples of substituents in the present specification are described below, but are not limited thereto.
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 replaced with another substituent, and the position to be substituted is not limited as long as the hydrogen atom is substituted, that is, a position where the substituent is substituted, and when two or more are substituted , Two or more substituents may be the same as 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; 또는 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.In this specification, the term "substituted or unsubstituted" means deuterium; halogen group; nitrile group (-CN); nitro group; hydroxy group; an alkyl group; cycloalkyl group; alkoxy group; phosphine oxide group; aryloxy group; Alkyl thioxy group; Arylthioxy group; an alkyl sulfoxy group; aryl sulfoxy group; alkenyl group; silyl group; boron group; amine group; aryl group; Or substituted with one or two or more substituents selected from the group consisting of heterocyclic groups, or substituted with substituents in which two or more substituents among the above exemplified substituents are connected, or without any substituents. For example, "a substituent in which two or more substituents are connected" may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 니트로기; 히드록시기; 아미노기; 실릴기; 붕소기; 알콕시기; 아릴옥시기; 알킬기; 시클로알킬기; 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. In this specification, the term "substituted or unsubstituted" means deuterium; halogen group; nitrile group; nitro group; hydroxy group; amino group; silyl group; boron group; alkoxy group; aryloxy group; an alkyl group; cycloalkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or is substituted with a substituent in which two or more substituents from among the above exemplified substituents are connected, or does not have any substituents.
본 명세서에서 "치환 또는 비치환된" 이라는 용어는 중수소; 할로겐기; 니트릴기; 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.In this specification, the term "substituted or unsubstituted" means deuterium; halogen group; nitrile group; an alkyl group; aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group, or is substituted with a substituent in which two or more substituents from among the above exemplified substituents are connected, or does not have any substituents.
상기 치환기들의 예시들은 아래에서 설명하나, 이에 한정되는 것은 아니다. Examples of the 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 the present specification, examples of the halogen group 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 a chemical formula of -SiY a Y b Y c , wherein Y a , Y b and Y c are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, and the like, but is not limited thereto. don't
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 트리메틸붕소기, 트리에틸붕소기, t-부틸디메틸붕소기, 트리페닐붕소기, 페닐붕소기 등이 있으나 이에 한정되지 않는다.In the present specification, the boron group may be represented by the chemical formula -BY d Y e , wherein Y d and Y e are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group. The boron group specifically includes a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, a phenyl boron group, but is not limited thereto.
본 명세서에 있어서, 상기 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 or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another exemplary embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group 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 is not limited thereto.
본 명세서에 있어서, 아릴알킬기는 아릴기로 치환된 것을 제외하고는 전술한 알킬기에 관한 설명이 적용될 수 있다.In the present specification, the description of the above-described alkyl group may be applied except that the arylalkyl group is substituted with an aryl group.
본 명세서에 있어서, 상기 알콕시기는 직쇄, 분지쇄 또는 고리쇄일 수 있다. 알콕시기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 20인 것이 바람직하다. 구체적으로, 메톡시, 에톡시, n-프로폭시, 이소프로폭시, 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 cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -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.Alkyl groups, alkoxy groups, and substituents containing other alkyl moieties described herein include both straight-chain and 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, 스티레닐기 등이 있으나 이들에 한정되지 않는다.In the present specification, the alkenyl group may be linear 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 exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styrenyl group, etc., but is not limited thereto.
본 명세서에 있어서, 상기 알키닐기는 탄소원자와 탄소원자 사이에 삼중결합을 포함하는 치환기로서, 직쇄 또는 분지쇄일 수 있고, 탄소수는 특별히 한정되지 않으나, 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면, 상기 알키닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알키닐기의 탄소수는 2 내지 10이다.In the present specification, the alkynyl group is a substituent including a triple bond between carbon atoms and may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkynyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkynyl group is 2 to 10.
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 an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to another exemplary embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, there are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like, but are 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 aforementioned 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 the substituted amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, 9,9-dimethylfluorenylphenylamine group, pyridylphenylamine group, diphenylamine group, phenylpyridylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, dibenzofuranylphenylamine group, 9-methylanthracenylamine group, diphenylamine group, phenylnaphthylamine group, A ditolylamine group, a phenyltolylamine group, a diphenylamine group, and the like, but are not limited thereto.
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, 트리페닐레닐기, 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 number of carbon atoms of the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the aryl group is 6 to 20. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, etc. as a monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenylenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is limited thereto it is not going to be
본 명세서에 있어서, 상기 아릴기는 단환으로 이루어진 아릴기 또는 다환 아릴기(2환 이상의 아릴기)일 수 있다. 단환으로 이루어진 아릴기는 페닐기; 또는 2개 이상의 페닐기가 연결되어 있는 기를 의미할 수 있다. 상기 단환으로 이루어진 아릴기로는 페닐기, 바이페닐기, 터페닐기, 쿼터페닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다. 다환 아릴기는 나프틸기, 페난트레닐기 등과 같이 단환 고리가 2 이상 축합되어 있는 기를 의미할 수 있다. 상기 다환 아릴기로는 나프틸기, 안트라세닐기, 페난트레닐기, 파이레닐기, 페릴레닐기, 트리페닐기, 크라이세닐기, 플루오레닐기, 트리페닐레닐기 등이 될 수 있으나, 이에 한정되는 것은 아니다.In the present specification, the aryl group may be a monocyclic aryl group or a polycyclic aryl group (two or more ring aryl groups). An aryl group consisting of a monocyclic ring may be a phenyl group; Or it may mean a group in which two or more phenyl groups are connected. The monocyclic aryl group may include, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, and the like. The polycyclic aryl group may mean a group in which two or more monocyclic rings are condensed, such as a naphthyl group and a phenanthrenyl group. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl 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. 이때, 스피로 구조는 방향족 탄화수소 고리 또는 지방족 탄화수소 고리일 수 있다.In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. At this time, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.
상기 플루오레닐기가 치환되는 경우,
Figure PCTKR2022009772-appb-img-000003
,
Figure PCTKR2022009772-appb-img-000004
,
Figure PCTKR2022009772-appb-img-000005
등의 스피로플루오레닐기,
Figure PCTKR2022009772-appb-img-000006
(9,9-디메틸플루오레닐기), 및
Figure PCTKR2022009772-appb-img-000007
(9,9-디페닐플루오레닐기) 등의 치환된 플루오레닐기가 될 수 있다. 다만, 이에 한정되는 것은 아니다.When the fluorenyl group is substituted,
Figure PCTKR2022009772-appb-img-000003
,
Figure PCTKR2022009772-appb-img-000004
,
Figure PCTKR2022009772-appb-img-000005
spirofluorenyl groups such as;
Figure PCTKR2022009772-appb-img-000006
(9,9-dimethylfluorenyl group), and
Figure PCTKR2022009772-appb-img-000007
It may be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.
본 명세서에 있어서, 아릴옥시기 중의 아릴기는 전술한 아릴기에 관한 설명이 적용될 수 있다.In the present specification, the aryl group in the aryloxy group may be applied to the above description of the aryl group.
본 명세서에 있어서, 상기 알킬티옥시기 및 알킬술폭시기 중의 알킬기에는 전술한 알킬기에 관한 설명이 적용될 수 있다.In the present specification, the description of the alkyl group described above may be applied to the alkyl group in the alkylthioxy group and the alkylsulfoxy group.
본 명세서에 있어서, 상기 아릴티옥시기 및 아릴술폭시기 중의 아릴기에는 전술한 아릴기에 관한 설명이 적용될 수 있다.In the present specification, the description of the aryl group described above may be applied to the aryl group among the arylthiooxy group and the arylsulfoxy 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 ring 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 preferably has 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 the heterocyclic group include a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, carba A sol group, a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, an indenocarbazole group, a triazinyl group, and the like, but are not limited thereto.
본 명세서에 있어서, 헤테로아릴기는 방향족인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다.In the present specification, the heterocyclic group described above may 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, 2가의 헤테로고리는 2가인 것을 제외하고는 상기 헤테로고리기에 대한 설명이 적용될 수 있다.In the present specification, the description of the heterocyclic group may be applied except that the divalent heterocyclic ring is divalent.
본 명세서에 있어서, 인접한 기와 서로 결합하여 형성되는 치환 또는 비치환된 고리에서, "고리"는 탄화수소 고리; 또는 헤테로 고리를 의미한다.In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups, "ring" refers to a hydrocarbon ring; or a heterocyclic ring.
상기 탄화수소 고리는 방향족, 지방족 또는 방향족과 지방족의 축합고리일 수 있으며, 상기 시클로알킬기 또는 아릴기의 예시 중에서 선택될 수 있다.The hydrocarbon ring may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or the 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 등의 원소 중에서 선택된 1 이상으로 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, the meaning of forming a ring by bonding with adjacent groups means a substituted or unsubstituted aliphatic hydrocarbon ring by bonding with adjacent groups; A substituted or unsubstituted aromatic hydrocarbon ring; A substituted or unsubstituted aliphatic heterocycle; A substituted or unsubstituted aromatic heterocycle; or to form a condensed ring thereof. The hydrocarbon ring means a ring composed of only carbon and hydrogen atoms. The heterocycle refers to a ring containing at least one selected from elements such as 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 is a non-aromatic ring and refers to a ring composed of only carbon and hydrogen atoms. Examples of the aliphatic hydrocarbon ring include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, etc. 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 the present specification, an aromatic hydrocarbon ring means an aromatic ring composed of only 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 and the like, but are not limited thereto. In the present specification, an aromatic hydrocarbon ring may be interpreted as 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.In the present specification, an aliphatic heterocycle means an aliphatic ring containing one or more of heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocaine , Thiocane, etc., but are 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.In the present specification, an aromatic heterocycle means an aromatic ring containing one or more of heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parasol, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thia Diazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine , phenanthridine, diazanaphthalene, driazainden, indole, indolizine, benzothiazole, benzooxazole, benzoimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzo carbazole, dibenzocarbazole, phenazine, imidazopyridine, phenoxazine, indolocarbazole, indenocarbazole, and the like, but are not limited thereto.
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 발명 화학식 1은 카바졸기와 아민기 사이에 특정 구조의 meta-바이페닐렌기 링커를 갖고, 바이페닐렌기 중 아민기에 직접결합된 페닐렌기에 추가의 치환기 R2를 포함하며, 아민기는 단환으로 이루어진 아릴기, 2환의 아릴기 또는 헤테로고리기를 포함하는 것이 특징이다. Formula 1 of the present invention has a meta-biphenylene linker of a specific structure between the carbazole group and the amine group, includes an additional substituent R2 to the phenylene group directly bonded to the amine group in the biphenylene group, and the amine group is an aryl composed of a monocyclic ring. It is characterized by including a group, a bicyclic aryl group or a heterocyclic group.
상기 특징을 갖는 화학식 1로 표시되는 화합물을 유기 발광 소자에 적용시, 고효율, 저전압 및/또는 장수명 특성을 가지는 유기 발광 소자를 얻을 수 있다. 반면, 아민기가 3환 이상의 아릴기를 포함하는 화합물을 사용하는 경우, 3환 이상의 아릴기가 단환 또는 2환의 아릴기보다 상대적으로 크기 때문에, 소자의 전압이 높고 효율이 낮아지는 경향을 보인다. 또한, 열안정성이 낮기 때문에 승화시 순도가 저하하는 경향이 있어 수명 특성 또한 저하되는 문제점이 있다. When the compound represented by Chemical Formula 1 having the above characteristics is applied to an organic light emitting device, an organic light emitting device having high efficiency, low voltage and/or long lifespan characteristics can be obtained. On the other hand, when using a compound in which the amine group includes a tricyclic or more ring aryl group, the voltage of the device tends to be high and the efficiency to be low because the tricyclic or more ring aryl group is relatively larger than the monocyclic or bicyclic aryl group. In addition, since the thermal stability is low, since the purity tends to decrease during sublimation, there is a problem in that life characteristics are also deteriorated.
이하, 화학식 1에 대하여 상세히 설명한다.Hereinafter, Formula 1 will be described in detail.
[화학식 1][Formula 1]
Figure PCTKR2022009772-appb-img-000008
Figure PCTKR2022009772-appb-img-000008
상기 화학식 1에 있어서,In Formula 1,
L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 단환으로 이루어진 아릴렌기; 또는 2환의 아릴렌기이고,L1 and L2 are the same as or different from each other, and are each independently a direct bond; An arylene group consisting of a monocycle; Or a bicyclic arylene group,
Ar1 및 Ar2은 서로 같거나 상이하고, 각각 독립적으로 단환으로 이루어진 아릴기; 2환의 아릴기; 및 헤테로고리기로 이루어진 군에서 선택된 하나이거나, 상기 군에서 선택된 2 이상의 기가 연결된 기이고,Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic aryl group; a bicyclic aryl group; And one selected from the group consisting of a heterocyclic group, or a group in which two or more groups selected from the group are connected,
R1은 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or bonded to adjacent groups to form a substituted or unsubstituted ring;
R2는 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,R2 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
a는 0 내지 8의 정수이고, a가 2 이상인 경우, 2 이상의 R1은 서로 같거나 상이하다.a is an integer from 0 to 8, and when a is 2 or more, 2 or more R1s are the same as or different from each other.
본 명세서의 일 실시상태에 있어서, L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 단환으로 이루어진 아릴렌기; 또는 2환의 아릴렌기이다.In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; An arylene group consisting of a monocycle; or a bicyclic arylene group.
본 명세서의 일 실시상태에 있어서, L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 단환으로 이루어진 탄소수 6 내지 60의 아릴렌기; 또는 2환의 아릴렌기이다.In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; A monocyclic arylene group having 6 to 60 carbon atoms; or a bicyclic arylene group.
본 명세서의 일 실시상태에 있어서, L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 단환으로 이루어진 탄소수 6 내지 30의 아릴렌기; 또는 2환의 아릴렌기이다.In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; A monocyclic arylene group having 6 to 30 carbon atoms; or a bicyclic arylene group.
본 명세서의 일 실시상태에 있어서, L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 또는 단환으로 이루어지거나, 2환의 탄소수 6 내지 30의 아릴렌기이다.In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; or a monocyclic or bicyclic arylene group having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 바이페닐렌기; 터페닐렌기; 또는 나프틸렌기이다.In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; phenylene group; biphenylene group; Terphenylene group; or a naphthylene group.
본 명세서의 일 실시상태에 있어서, L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 페닐렌기; 바이페닐렌기; 또는 나프틸렌기이다.In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and are each independently a direct bond; phenylene group; biphenylene group; or a naphthylene group.
본 명세서의 일 실시상태에 있어서, L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합이거나, 하기 구조식 중 어느 하나로 표시된다.In one embodiment of the present specification, L1 and L2 are the same as or different from each other, and each independently represents a direct bond or one of the following structural formulas.
Figure PCTKR2022009772-appb-img-000009
Figure PCTKR2022009772-appb-img-000009
상기 구조식에서 점선은 결합위치를 의미한다.In the above structural formula, the dotted line means the binding position.
본 명세서의 일 실시상태에 있어서, Ar1 및 Ar2은 서로 같거나 상이하고, 각각 독립적으로 단환으로 이루어진 아릴기; 2환의 아릴기; 및 헤테로고리기로 이루어진 군에서 선택된 하나이거나, 상기 군에서 선택된 2 이상의 기가 연결된 기이다.In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic aryl group; a bicyclic aryl group; And one selected from the group consisting of a heterocyclic group, or a group in which two or more groups selected from the above group are connected.
본 명세서의 일 실시상태에 있어서, Ar1 및 Ar2은 서로 같거나 상이하고, 각각 독립적으로 단환으로 이루어진 탄소수 6 내지 60의 아릴기; 2환의 아릴기; 및 탄소수 2 내지 60의 헤테로고리기로 이루어진 군에서 선택된 하나이거나, 상기 군에서 선택된 2 이상의 기가 연결된 기이다.In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic aryl group having 6 to 60 carbon atoms; a bicyclic aryl group; And one selected from the group consisting of a heterocyclic group having 2 to 60 carbon atoms, or a group in which two or more groups selected from the above group are connected.
본 명세서의 일 실시상태에 있어서, Ar1 및 Ar2은 서로 같거나 상이하고, 각각 독립적으로 단환으로 이루어진 탄소수 6 내지 30의 아릴기; 2환의 아릴기; 및 탄소수 2 내지 30의 헤테로고리기로 이루어진 군에서 선택된 하나이거나, 상기 군에서 선택된 2 이상의 기가 연결된 기이다.In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic aryl group having 6 to 30 carbon atoms; a bicyclic aryl group; and a heterocyclic group having 2 to 30 carbon atoms, or a group in which two or more groups selected from the group are connected.
본 명세서의 일 실시상태에 있어서, Ar1 및 Ar2은 서로 같거나 상이하고, 각각 독립적으로 단환으로 이루어진 탄소수 6 내지 30의 아릴기; 2환의 아릴기; 및 탄소수 2 내지 30의 O 또는 S 함유 헤테로고리기로 이루어진 군에서 선택된 하나이거나, 상기 군에서 선택된 2 이상의 기가 연결된 기이다.In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic aryl group having 6 to 30 carbon atoms; a bicyclic aryl group; and a group consisting of O or S-containing heterocyclic groups having 2 to 30 carbon atoms, or a group in which two or more groups selected from the above group are connected.
본 명세서의 일 실시상태에 있어서, Ar1 및 Ar2은 서로 같거나 상이하고, 각각 독립적으로 단환으로 이루어진 탄소수 6 내지 30의 아릴기; 2환의 아릴기; 및 탄소수 2 내지 30의 O 또는 S 함유 헤테로고리기로 이루어진 군에서 선택된 하나이거나, 단환으로 이루어진 탄소수 6 내지 30의 아릴기; 및 2환의 아릴기로 이루어진 군에서 선택된 2 이상의 기가 연결된 기이다.In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic aryl group having 6 to 30 carbon atoms; a bicyclic aryl group; And one selected from the group consisting of O or S-containing heterocyclic groups having 2 to 30 carbon atoms, or a monocyclic aryl group having 6 to 30 carbon atoms; and a group in which two or more groups selected from the group consisting of bicyclic aryl groups are connected.
본 명세서의 일 실시상태에 있어서, Ar1 및 Ar2은 서로 같거나 상이하고, 각각 독립적으로 단환으로 이루어진 아릴기 또는 2환의 아릴기로 치환 또는 비치환된 페닐기; 단환으로 이루어진 아릴기 또는 2환의 아릴기로 치환 또는 비치환된 바이페닐기; 단환으로 이루어진 아릴기 또는 2환의 아릴기로 치환 또는 비치환된 터페닐기; 단환으로 이루어진 아릴기 또는 2환의 아릴기로 치환 또는 비치환된 쿼터페닐기; 단환으로 이루어진 아릴기 또는 2환의 아릴기로 치환 또는 비치환된 나프틸기; 단환으로 이루어진 아릴기 또는 2환의 아릴기로 치환 또는 비치환된 디벤조퓨란기; 또는 단환으로 이루어진 아릴기 또는 2환의 아릴기로 치환 또는 비치환된 디벤조티오펜기이다. In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic aryl group or a phenyl group unsubstituted or substituted with a bicyclic aryl group; A biphenyl group unsubstituted or substituted with a monocyclic aryl group or a bicyclic aryl group; A terphenyl group unsubstituted or substituted with a monocyclic aryl group or a bicyclic aryl group; a quarterphenyl group unsubstituted or substituted with a monocyclic aryl group or a bicyclic aryl group; a naphthyl group unsubstituted or substituted with a monocyclic aryl group or a bicyclic aryl group; a dibenzofuran group unsubstituted or substituted with a monocyclic aryl group or a bicyclic aryl group; or a dibenzothiophene group unsubstituted or substituted with a monocyclic aryl group or a bicyclic aryl group.
본 명세서의 일 실시상태에 있어서, Ar1 및 Ar2은 서로 같거나 상이하고, 각각 독립적으로 페닐기, 바이페닐기, 터페닐기 또는 나프틸기로 치환 또는 비치환된 페닐기; 페닐기, 바이페닐기, 터페닐기 또는 나프틸기로 치환 또는 비치환된 바이페닐기; 페닐기, 바이페닐기, 터페닐기 또는 나프틸기로 치환 또는 비치환된 터페닐기; 페닐기, 바이페닐기, 터페닐기 또는 나프틸기로 치환 또는 비치환된 쿼터페닐기; 페닐기, 바이페닐기, 터페닐기 또는 나프틸기로 치환 또는 비치환된 나프틸기; 디벤조퓨란기; 또는 디벤조티오펜기이다.In an exemplary embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group; A phenyl group, a biphenyl group, a terphenyl group, or a substituted or unsubstituted biphenyl group with a naphthyl group; A terphenyl group unsubstituted or substituted with a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group; Quarterphenyl group unsubstituted or substituted with a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group; a naphthyl group unsubstituted or substituted with a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group; Dibenzofuran group; or a dibenzothiophene group.
본 명세서의 일 실시상태에 있어서, Ar1 및 Ar2은 서로 같거나 상이하고, 각각 독립적으로 나프틸기로 치환 또는 비치환된 페닐기; 나프틸기로 치환 또는 비치환된 바이페닐기; 터페닐기; 쿼터페닐기; 페닐기 또는 바이페닐기로 치환 또는 비치환된 나프틸기; 디벤조퓨란기; 또는 디벤조티오펜기이다. In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a naphthyl group; A biphenyl group unsubstituted or substituted with a naphthyl group; terphenyl group; Quarter phenyl group; a naphthyl group unsubstituted or substituted with a phenyl group or a biphenyl group; Dibenzofuran group; or a dibenzothiophene group.
본 명세서의 일 실시상태에 있어서, Ar1 및 Ar2는 서로 같거나 상이하고, 각각 독립적으로 하기 구조식 중 어느 하나로 표시된다.In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently represented by any one of the following structural formulas.
Figure PCTKR2022009772-appb-img-000010
Figure PCTKR2022009772-appb-img-000010
상기 구조식에 있어서, 점선은 결합위치를 의미한다.In the above structural formula, the dotted line means the binding position.
본 명세서의 일 실시상태에 있어서, Ar1 및 Ar2 중 적어도 하나는 단환으로 이루어진 아릴기; 및 2환의 아릴기로 이루어진 군에서 선택된 하나이거나, 상기 군에서 선택된 2 이상의 기가 연결된 기이다.In one embodiment of the present specification, at least one of Ar1 and Ar2 is a monocyclic aryl group; and a bicyclic aryl group, or a group in which two or more groups selected from the group are connected.
본 명세서의 일 실시상태에 있어서, Ar1 및 Ar2 중 적어도 하나는 단환으로 이루어진 아릴기; 및 2환의 아릴기로 이루어진 군에서 선택된 하나이거나, 상기 군에서 선택된 2 이상의 기가 연결된 기이다.In one embodiment of the present specification, at least one of Ar1 and Ar2 is a monocyclic aryl group; and a bicyclic aryl group, or a group in which two or more groups selected from the group are connected.
본 명세서의 일 실시상태에 있어서, Ar1 및 Ar2 중 적어도 하나는 헤테로고리기이다.In one embodiment of the present specification, at least one of Ar1 and Ar2 is a heterocyclic group.
본 명세서의 일 실시상태에 있어서, R1은 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성한다.In one embodiment of the present specification, R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or bonded to adjacent groups to form a substituted or unsubstituted ring.
본 명세서의 일 실시상태에 있어서, R1은 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 30의 알킬기; 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로고리기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 2 내지 60의 고리를 형성한다.In one embodiment of the present specification, R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or bonded to an adjacent group to form a substituted or unsubstituted ring having 2 to 60 carbon atoms.
본 명세서의 일 실시상태에 있어서, R1은 수소; 중수소; 치환 또는 비치환된 탄소수 1 내지 20의 알킬기; 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 탄소수 2 내지 30의 고리를 형성한다.In one embodiment of the present specification, R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or bonded to an adjacent group to form a substituted or unsubstituted ring having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, R1은 수소; 중수소; 탄소수 1 내지 20의 알킬기; 탄소수 6 내지 30의 아릴기; 또는 탄소수 2 내지 30의 헤테로고리기이거나, 인접한 기와 서로 결합하여 탄소수 6 내지 30의 방향족 탄화수소고리를 형성한다.In one embodiment of the present specification, R1 is hydrogen; heavy hydrogen; an alkyl group having 1 to 20 carbon atoms; an aryl group having 6 to 30 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms, or bonded to an adjacent group to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, R1은 수소; 또는 중수소이거나, 인접한 기와 서로 결합하여 탄소수 6 내지 30의 방향족 탄화수소고리를 형성한다.In one embodiment of the present specification, R1 is hydrogen; Or deuterium, or bonded to adjacent groups to form an aromatic hydrocarbon ring having 6 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, R1은 수소; 또는 중수소이거나, 인접한 기와 서로 결합하여 벤젠고리를 형성한다.In one embodiment of the present specification, R1 is hydrogen; Or deuterium, or bonded to adjacent groups to form a benzene ring.
본 명세서의 일 실시상태에 있어서, R1은 수소; 또는 중수소이다.In one embodiment of the present specification, R1 is hydrogen; or deuterium.
본 명세서의 일 실시상태에 있어서, R1은 수소이다.In one embodiment of the present specification, R1 is hydrogen.
본 명세서의 일 실시상태에 있어서, R2는 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이다.In one embodiment of the present specification, R2 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
본 명세서의 일 실시상태에 있어서, R2는 치환 또는 비치환된 탄소수 6 내지 60의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 60의 헤테로고리기이다.In one embodiment of the present specification, R2 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
본 명세서의 일 실시상태에 있어서, R2는 치환 또는 비치환된 탄소수 6 내지 30의 아릴기; 또는 치환 또는 비치환된 탄소수 2 내지 30의 헤테로고리기이다.In one embodiment of the present specification, R2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, R2는 탄소수 6 내지 30의 아릴기; 또는 탄소수 2 내지 30의 헤테로고리기이다.In one embodiment of the present specification, R2 is an aryl group having 6 to 30 carbon atoms; or a heterocyclic group having 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, R2는 탄소수 6 내지 30의 아릴기; 또는 탄소수 2 내지 30의 O 또는 S 함유 헤테로고리기이다.In one embodiment of the present specification, R2 is an aryl group having 6 to 30 carbon atoms; or a heterocyclic group containing O or S of 2 to 30 carbon atoms.
본 명세서의 일 실시상태에 있어서, R2는 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 디벤조퓨란기; 또는 치환 또는 비치환된 디벤조티오펜기이다.In one embodiment of the present specification, R2 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.
본 명세서의 일 실시상태에 있어서, R2는 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 디벤조퓨란기; 또는 치환 또는 비치환된 디벤조티오펜기이다.In one embodiment of the present specification, R2 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.
본 명세서의 일 실시상태에 있어서, R2는 페닐기; 바이페닐기; 나프틸기; 페난트레닐기; 디벤조퓨란기; 또는 디벤조티오펜기이다.In one embodiment of the present specification, R2 is a phenyl group; biphenyl group; naphthyl group; phenanthrenyl group; Dibenzofuran group; or a dibenzothiophene group.
본 명세서의 일 실시상태에 있어서, R2는 페닐기; 바이페닐기; 나프틸기; 페난트레닐기; 또는 디벤조퓨란기이다.In one embodiment of the present specification, R2 is a phenyl group; biphenyl group; naphthyl group; phenanthrenyl group; or a dibenzofuran group.
본 명세서의 일 실시상태에 있어서, R2는 하기 구조식 중 어느 하나로 표시된다.In one embodiment of the present specification, R2 is represented by any one of the following structural formulas.
Figure PCTKR2022009772-appb-img-000011
Figure PCTKR2022009772-appb-img-000011
상기 구조식에 있어서, 점선은 결합 위치를 의미한다.In the above structural formula, the dotted line means the binding position.
본 명세서의 일 실시상태에 있어서, R2는 하기 구조식 중 어느 하나로 표시된다.In one embodiment of the present specification, R2 is represented by any one of the following structural formulas.
Figure PCTKR2022009772-appb-img-000012
Figure PCTKR2022009772-appb-img-000012
상기 구조식에 있어서, 점선은 결합 위치를 의미한다.In the above structural formula, the dotted line means the binding position.
본 명세서의 일 실시상태에 있어서, a는 0 내지 8의 정수이다.In one embodiment of the present specification, a is an integer from 0 to 8.
본 명세서의 일 실시상태에 있어서, a는 0이다.In one embodiment of the present specification, a is 0.
본 명세서의 일 실시상태에 있어서, a는 1이다.In one embodiment of the present specification, a is 1.
본 명세서의 일 실시상태에 있어서, a는 8이다.In one embodiment of the present specification, a is 8.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 1-1 내지 1-5 중 어느 하나로 표시된다.In one embodiment of the present specification, Formula 1 is represented by any one of Formulas 1-1 to 1-5 below.
[화학식 1-1][Formula 1-1]
Figure PCTKR2022009772-appb-img-000013
Figure PCTKR2022009772-appb-img-000013
[화학식 1-2][Formula 1-2]
Figure PCTKR2022009772-appb-img-000014
Figure PCTKR2022009772-appb-img-000014
[화학식 1-3][Formula 1-3]
Figure PCTKR2022009772-appb-img-000015
Figure PCTKR2022009772-appb-img-000015
[화학식 1-4][Formula 1-4]
Figure PCTKR2022009772-appb-img-000016
Figure PCTKR2022009772-appb-img-000016
[화학식 1-5][Formula 1-5]
Figure PCTKR2022009772-appb-img-000017
Figure PCTKR2022009772-appb-img-000017
상기 화학식 1-1 내지 1-5에 있어서, L1, L2, Ar1, Ar2, R1 및 a의 정의는 상기 화학식 1에서 정의한 바와 같고,In Formulas 1-1 to 1-5, the definitions of L1, L2, Ar1, Ar2, R1 and a are as defined in Formula 1,
X는 O; 또는 S이다.X is O; or S.
본 명세서의 일 실시상태에 있어서, X는 O이다.In one embodiment of the present specification, X is O.
본 명세서의 일 실시상태에 있어서, X는 S이다.In one embodiment of the present specification, X is S.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화학식 1-1 및 2-1 내지 2-9 중 어느 하나로 표시된다.In one embodiment of the present specification, Chemical Formula 1 is represented by any one of Chemical Formulas 1-1 and 2-1 to 2-9.
[화학식 1-1][Formula 1-1]
Figure PCTKR2022009772-appb-img-000018
Figure PCTKR2022009772-appb-img-000018
[화학식 2-1]　　　　　　　　　　　　　　　　[화학식 2-2][Formula 2-1] [Formula 2-1] [Formula 2-2]
Figure PCTKR2022009772-appb-img-000019
Figure PCTKR2022009772-appb-img-000019
[화학식 2-3]　　　　　　　　　　　　　　　　[화학식 2-4][Formula 2-3] [Formula 2-3] [Formula 2-4]
Figure PCTKR2022009772-appb-img-000020
Figure PCTKR2022009772-appb-img-000020
[화학식 2-5][Formula 2-5]
Figure PCTKR2022009772-appb-img-000021
Figure PCTKR2022009772-appb-img-000021
[화학식 2-6]　　　　　　　　　　　　　　　　[화학식 2-7][Formula 2-6] [Formula 2-6] [Formula 2-7]
Figure PCTKR2022009772-appb-img-000022
Figure PCTKR2022009772-appb-img-000022
[화학식 2-8]　　　　　　　　　　　　　　　　[화학식 2-9][Formula 2-8] [Formula 2-8] [Formula 2-9]
Figure PCTKR2022009772-appb-img-000023
Figure PCTKR2022009772-appb-img-000023
상기 화학식 1-1 및 2-1 내지 2-9에 있어서, L1, L2, Ar1, Ar2, R1 및 a의 정의는 상기 화학식 1에서 정의한 바와 같고,In Formulas 1-1 and 2-1 to 2-9, the definitions of L1, L2, Ar1, Ar2, R1 and a are as defined in Formula 1,
X는 O; 또는 S이다.X is O; or S.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1은 하기 화합물 중 어느 하나로 표시된다.In one embodiment of the present specification, Formula 1 is represented by any one of the following compounds.
Figure PCTKR2022009772-appb-img-000024
Figure PCTKR2022009772-appb-img-000024
Figure PCTKR2022009772-appb-img-000025
Figure PCTKR2022009772-appb-img-000025
Figure PCTKR2022009772-appb-img-000026
Figure PCTKR2022009772-appb-img-000026
Figure PCTKR2022009772-appb-img-000027
Figure PCTKR2022009772-appb-img-000027
Figure PCTKR2022009772-appb-img-000028
Figure PCTKR2022009772-appb-img-000028
Figure PCTKR2022009772-appb-img-000029
Figure PCTKR2022009772-appb-img-000029
Figure PCTKR2022009772-appb-img-000030
Figure PCTKR2022009772-appb-img-000030
Figure PCTKR2022009772-appb-img-000031
Figure PCTKR2022009772-appb-img-000031
Figure PCTKR2022009772-appb-img-000032
Figure PCTKR2022009772-appb-img-000032
Figure PCTKR2022009772-appb-img-000033
Figure PCTKR2022009772-appb-img-000033
Figure PCTKR2022009772-appb-img-000034
Figure PCTKR2022009772-appb-img-000034
Figure PCTKR2022009772-appb-img-000035
Figure PCTKR2022009772-appb-img-000035
본 명세서의 일 실시상태에 따른 화학식 1로 표시되는 화합물은 하기 반응식 1과 같이 코어구조가 제조될 수 있다. 치환기는 당 기술분야에 알려져 있는 방법에 의하여 결합될 수 있으며, 치환기의 종류, 위치 또는 개수는 당 기술분야에 알려져 있는 기술에 따라 변경될 수 있다.A compound represented by Formula 1 according to an exemplary embodiment of the present specification may have a core structure as shown in Reaction Scheme 1 below. Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art.
<반응식 1><Scheme 1>
Figure PCTKR2022009772-appb-img-000036
Figure PCTKR2022009772-appb-img-000036
상기 반응식 1에 있어서, 치환기의 정의는 상기 화학식 1에서의 정의와 같다.In Reaction Scheme 1, the definition of the substituent is the same as the definition in Formula 1 above.
상기 반응식 1에서는 특정위치에 특정 치환기가 결합된 화합물을 합성하는 과정을 예시하였으나, 당 기술분야에 알려져있는 출발물질, 중간물질 등을 이용하여 당 기술분야에 알려져있는 합성방법에 의하여 상기 화학식 1의 범위에 해당하는 화합물들을 합성할 수 있다.In Reaction Scheme 1, a process for synthesizing a compound having a specific substituent bonded to a specific position was exemplified, but by a synthetic method known in the art using starting materials and intermediate materials known in the art, Compounds corresponding to the range can be synthesized.
본 명세서에서는 상기 화학식 1로 표시되는 화합물의 코어 구조에 다양한 치환기를 도입함으로써 다양한 에너지 밴드갭을 갖는 화합물을 합성할 수 있다. 또한, 본 명세서에서는 상기와 같은 구조의 코어 구조에 다양한 치환기를 도입함으로써 화합물의 HOMO 및 LUMO 에너지 준위도 조절할 수 있다.In the present specification, compounds having various energy band gaps may be synthesized by introducing various substituents into the core structure of the compound represented by Formula 1. In addition, in the present specification, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents into the core structure of the above structure.
또한, 본 명세서는 상기 전술한 화합물을 포함하는 유기 발광 소자를 제공한다.In addition, the present specification provides an organic light emitting device including the aforementioned compound.
본 명세서에서 어떤 부재가 다른 부재 "상에" 위치하고 있다고 할 때, 이는 어떤 부재가 다른 부재에 접해 있는 경우뿐 아니라 두 부재 사이에 또 다른 부재가 존재하는 경우도 포함한다.In this specification, when a member is said to be located “on” another member, this includes not only the case where a member is in contact with another member, but also the case where another member exists between the two members.
본 명세서에서 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성 요소를 더 포함할 수 있는 것을 의미한다. In this specification, when a part is said to "include" a certain component, it means that it may further include other components without excluding other components unless otherwise stated.
본 명세서에 따른 유기발광소자는 애노드; 캐소드; 및 상기 애노드와 상기 캐소드 사이에 구비된 1층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1 층 이상은 전술한 화학식 1로 표시되는 것인 화합물을 포함하는 것을 특징으로 한다.An organic light emitting device according to the present specification includes an anode; cathode; and one or more organic material layers provided between the anode and the cathode, wherein at least one of the organic material layers includes a compound represented by Formula 1 above.
본 명세서의 유기 발광 소자는 전술한 화학식 1의 화합물을 이용하여 유기물층을 형성하는 것을 제외하고는, 통상의 유기 발광 소자의 제조방법 및 재료에 의하여 제조될 수 있다.The organic light emitting device of the present specification may be manufactured by a conventional organic light emitting device manufacturing method and material, except for forming an organic material layer using the compound of Formula 1 described above.
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 as 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 coating method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.
본 명세서의 유기발광소자의 유기물층은 단층 구조로 이루어질 수도 있으나, 2층 이상의 유기물층이 적층된 다층 구조로 이루어질 수 있다. 예컨대, 본 발명의 유기발광소자는 유기물층으로서 정공수송층, 정공주입층, 전자차단층, 정공수송 및 주입 층, 전자수송층, 전자주입층, 정공차단층, 및 전자수송 및 주입층 중 1층 이상을 포함하는 구조를 가질 수 있다. 그러나, 본 명세서의 유기발광소자의 구조는 이에 한정되지 않고 더 적은 수 또는 더 많은 수의 유기물층을 포함할 수 있다.The organic material layer of the organic light emitting device of the present specification may have a single-layer structure, or may have a multi-layer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention includes at least one of a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as an organic material layer. may have a structure that includes However, the structure of the organic light emitting device of the present specification is not limited thereto and may include fewer or more organic material layers.
본 명세서의 유기발광소자에서, 상기 유기물층은 정공주입층, 정공수송층, 또는 정공 주입 및 수송층을 포함하고, 상기 정공주입층, 정공수송층, 또는 정공 주입 및 수송층은 전술한 화학식 1로 표시되는 화합물을 포함할 수 있다.In the organic light emitting device of the present specification, the organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, the hole transport layer, or the hole injection and transport layer comprises a compound represented by the above-described formula (1). can include
본 명세서의 유기발광소자에서, 상기 유기물층은 정공수송층 또는 정공주입층을 포함하고, 상기 정공수송층 또는 정공주입층은 전술한 화학식 1로 표시되는 화합물을 포함할 수 있다.In the organic light emitting device of the present specification, the organic material layer may include a hole transport layer or a hole injection layer, and the hole transport layer or hole injection layer may include the compound represented by Chemical Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 전자차단층을 포함하고, 상기 전자차단층은 상기 화학식 1로 표시되는 화합물을 포함한다. In one embodiment of the present specification, the organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound represented by Chemical Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 전자주입층, 전자수송층, 전자 수송 및 주입층 또는 정공차단층을 포함하고, 상기 전자주입층, 전자수송층, 전자 수송 및 주입층 또는 정공차단층은 전술한 화학식 1로 표시되는 화합물을 포함할 수 있다.In one embodiment of the present specification, the organic material layer includes an electron injection layer, an electron transport layer, an electron transport and injection layer, or a hole blocking layer, and the electron injection layer, the electron transport layer, the electron transport and injection layer, or the hole blocking layer It may include the compound represented by Formula 1 above.
본 명세서의 유기발광소자에서, 상기 유기물층은 전자수송층, 전자주입층, 또는 전자 수송 및 주입층을 포함하고, 상기 전자수송층, 전자주입층, 또는 전자 수송 및 주입층은 전술한 화학식 1로 표시되는 화합물을 포함할 수 있다.In the organic light emitting device of the present specification, the organic material layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer, and the electron transport layer, the electron injection layer, or the electron transport and injection layer is represented by the above-described formula (1) compounds may be included.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 전자조절층을 포함하고, 상기 전자조절층은 전술한 화학식 1로 표시되는 화합물을 포함할 수 있다.In one embodiment of the present specification, the organic material layer may include an electron control layer, and the electron control layer may include the compound represented by Formula 1 described above.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 정공차단층을 포함하고, 상기 정공차단층은 상기 화학식 1로 표시되는 화합물을 포함한다. In one embodiment of the present specification, the organic material layer includes a hole blocking layer, and the hole blocking layer includes the compound represented by Chemical Formula 1.
본 명세서의 유기발광소자에서, 상기 유기물층은 전자 수송 및 주입층이고, 상기 전자 수송 및 주입층은 전술한 화학식 1로 표시되는 화합물을 포함한다.In the organic light emitting device of the present specification, the organic material layer is an electron transport and injection layer, and the electron transport and injection layer includes the compound represented by Formula 1 above.
본 명세서의 일 실시상태에 있어서, 상기 화학식 1의 화합물을 포함하는 유기물층의 두께는 5 Å 내지 2000 Å이거나, 5 Å 내지 500 Å일 수 있고, 바람직하게는 10 Å 내지 200 Å이다.In one embodiment of the present specification, the thickness of the organic material layer including the compound of Formula 1 may be 5 Å to 2000 Å, 5 Å to 500 Å, and preferably 10 Å to 200 Å.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 전술한 화학식 1로 표시되는 화합물을 포함한다.In one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 above.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 전술한 화학식 1로 표시되는 화합물을 호스트로서 포함한다.In one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 as a host.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 전술한 화학식 1로 표시되는 화합물을 도펀트로서 포함한다.In one embodiment of the present specification, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Formula 1 as a dopant.
또 하나의 실시상태에 있어서, 상기 유기물층은 전술한 화학식 1로 표시되는 화합물 외에 다른 유기화합물, 금속 또는 금속화합물을 더 포함할 수 있다.In another exemplary embodiment, the organic material layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by Chemical Formula 1 described above.
본 명세서의 일 실시상태에 따른 유기 발광 소자에서, 상기 발광층은 형광 도펀트 또는 인광 도펀트를 더 포함한다. 이때, 발광층 내의 도펀트는 호스트 100 중량부 대비 1 중량부 내지 50 중량부로 포함된다.In the organic light emitting device according to one embodiment of the present specification, the light emitting layer further includes a fluorescent dopant or a phosphorescent dopant. At this time, the dopant in the light emitting layer is included in 1 part by weight to 50 parts by weight based on 100 parts by weight of the host.
또 하나의 예로서, 상기 유기물층은 발광층을 포함하고, 상기 발광층은 상기 화학식 1로 표시되는 화합물을 호스트로서 포함하고, 추가의 호스트를 더 포함할 수 있다. As another example, the organic material layer includes a light emitting layer, and the light emitting layer includes the compound represented by Chemical Formula 1 as a host and may further include an additional host.
본 명세서의 일 실시상태에 있어서, 상기 도펀트는 아릴아민계 화합물, 붕소 및 질소를 포함한 헤테로고리 화합물 또는 Ir 착체 등을 포함한다.In one embodiment of the present specification, the dopant includes an arylamine-based compound, a heterocyclic compound including boron and nitrogen, or an Ir complex.
본 명세서의 유기 발광 소자는 정공수송층, 정공주입층, 전자차단층, 전자수송 및 주입층, 전자수송층, 전자주입층, 정공차단층, 및 정공주입 및 수송층 중 1 층 이상의 유기물층을 더 포함할 수 있다.The organic light emitting device of the present specification may further include one or more organic material layers of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole injection and transport layer. there is.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 애노드; 캐소드; 및 상기 애노드와 상기 캐소드 사이에 구비된 2층 이상의 유기물층을 포함하고, 상기 2층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. In one embodiment of the present specification, the organic light emitting device includes an anode; cathode; and two or more organic material layers provided between the anode and the cathode, wherein at least one of the two or more organic material layers includes the compound represented by Chemical Formula 1.
본 명세서의 일 실시상태에 있어서, 상기 2층 이상의 유기물층은 발광층, 정공 수송층, 정공 주입층, 정공 수송 및 주입층 및 전자 차단층으로 이루어진 군에서 2 이상이 선택될 수 있다.In one embodiment of the present specification, the two or more organic material layers may be two or more selected from the group consisting of a light emitting layer, a hole transport layer, a hole injection layer, a hole transport and injection layer, and an electron blocking layer.
본 명세서의 일 실시상태에 있어서, 상기 2층 이상의 유기물층은 발광층, 전자수송층, 전자주입층, 전자 수송 및 주입층, 전자조절층 및 정공 차단층으로 이루어진 군에서 2 이상이 선택될 수 있다.In one embodiment of the present specification, the two or more organic material layers may be two or more selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron control layer, and a hole blocking layer.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 2층 이상의 전자 수 송층을 포함하고, 상기 2층 이상의 전자 수송층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 구체적으로 본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 2층 이상의 전자 수송층 중 1층에 포함될 수도 있으며, 각각의 2층 이상의 전자 수송층에 포함될 수 있다. In one embodiment of the present specification, the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the compound represented by Chemical Formula 1. Specifically, in one embodiment of the present specification, the compound represented by Formula 1 may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
또한, 본 명세서의 일 실시상태에 있어서, 상기 화합물이 상기 각각의 2층 이상의 전자 수송층에 포함되는 경우, 상기 화학식 1로 표시되는 화합물을 제외한 다른 재료들은 서로 동일하거나 상이할 수 있다.In addition, in one embodiment of the present specification, when the compound is included in each of the two or more electron transport layers, materials other than the compound represented by Formula 1 may be the same as or different from each other.
상기 화학식 1로 표시되는 화합물을 포함하는 유기물층이 전자수송층, 전자주입층, 또는 전자 수송 및 주입층인 경우, 상기 전자수송층, 전자주입층, 또는 전자 수송 및 주입층은 n형 도펀트 또는 유기 금속 화합물을 더 포함할 수 있다. 상기 n형 도펀트 또는 유기 금속 화합물은 당 기술분야에 알려져 있는 것들을 사용할 수 있으며, 예컨대 금속 또는 금속착체를 사용할 수 있다.When the organic material layer containing the compound represented by Formula 1 is an electron transport layer, an electron injection layer, or an electron transport and injection layer, the electron transport layer, the electron injection layer, or the electron transport and injection layer is an n-type dopant or an organometallic compound. may further include. As the n-type dopant or organometallic compound, those known in the art may be used, and for example, a metal or a metal complex may be used.
예를 들어, 상기 n형 도펀트 또는 유기 금속 화합물은 LiQ일 수 있고, 이에 한정되는 것은 아니다. 상기 화학식 1로 표시되는 화합물을 포함하는 전자수송층, 전자주입층, 또는 전자 수송 및 주입층은 LiQ(Lithium Quinolate)를 더 포함할 수 있다. For example, the n-type dopant or organometallic compound may be LiQ, but is not limited thereto. The electron transport layer, the electron injection layer, or the electron transport and injection layer including the compound represented by Formula 1 may further include lithium quinolate (LiQ).
일 예에 따르면, 상기 화학식 1로 표시되는 화합물과 상기 n형 도펀트 또는 유기 금속 화합물은 2:8 내지 8:2, 예컨대 4:6 내지 6:4의 중량비로 포함될 수 있다. 일 예에 따르면, 상기 화학식 1로 표시되는 화합물과 상기 n형 도펀트 또는 유기 금속 화합물은 1:1의 중량비로 포함될 수 있다.According to one example, the compound represented by Chemical Formula 1 and the n-type dopant or organometallic compound may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4. According to one example, the compound represented by Chemical Formula 1 and the n-type dopant or organometallic compound may be included in a weight ratio of 1:1.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 2층 이상의 정공수송층을 포함하고, 상기 2층 이상의 정공 수송층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 구체적으로, 본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물은 상기 2층 이상의 정공 수송층 중 1층에 포함될 수도 있으며, 각각의 2층 이상의 정공 수송층에 포함될 수 있다. In one embodiment of the present specification, the organic material layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes the compound represented by Chemical Formula 1. Specifically, in one embodiment of the present specification, the compound represented by Chemical Formula 1 may be included in one of the two or more hole transport layers, and may be included in each of the two or more hole transport layers.
또한, 본 명세서의 일 실시상태에 있어서, 상기 화학식 1로 표시되는 화합물이 상기 각각의 2층 이상의 정공 수송층에 포함되는 경우, 상기 화학식 1로 표시되는 화합물을 제외한 다른 재료들은 서로 동일하거나 상이할 수 있다.In addition, in one embodiment of the present specification, when the compound represented by Formula 1 is included in each of the two or more hole transport layers, materials other than the compound represented by Formula 1 may be the same or different from each other. there is.
본 명세서의 일 실시상태에 있어서, 상기 유기물층은 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층 이외에 아릴아민기, 카바졸릴기 또는 벤조카바졸릴기를 포함하는 화합물을 포함하는 정공 주입층 또는 정공 수송층을 더 포함할 수 있다.In one embodiment of the present specification, the organic material layer further includes a hole injection layer or a hole transport layer containing a compound containing an arylamine group, a carbazolyl group, or a benzocarbazolyl group in addition to the organic material layer containing the compound represented by Formula 1 can include
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 기판 상에 애노드, 1층 이상의 유기물층 및 캐소드가 순차적으로 적층된 구조(normal type)의 유기 발광 소자일 수 있다. In one embodiment of the present specification, the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
본 명세서의 일 실시상태에 있어서, 상기 유기 발광 소자는 기판 상에 캐소드, 1층 이상의 유기물층 및 애노드가 순차적으로 적층된 역방향 구조(inverted type)의 유기 발광 소자일 수 있다.In one embodiment of the present specification, the organic light emitting device may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
본 발명의 유기 발광 소자에서, 상기 유기물층은 전자차단층을 포함할 수 있으며, 상기 전자차단층은 당 기술분야에 알려져 있는 재료가 사용될 수 있다.In the organic light emitting device of the present invention, the organic material layer may include an electron blocking layer, and materials known in the art may be used for the electron blocking layer.
상기 유기 발광 소자는 예컨대 하기와 같은 적층 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.The organic light emitting device may have, for example, a stacked structure as described below, 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/정공주입층/정공버퍼층/정공수송층/발광층/캐소드(3) anode/hole injection layer/hole buffer layer/hole transport layer/light emitting layer/cathode
(4) 애노드/정공수송층/발광층/전자수송층/캐소드(4) anode/hole transport layer/light emitting layer/electron transport layer/cathode
(5) 애노드/정공수송층/발광층/전자수송층/전자주입층/캐소드(5) anode/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(6) 애노드/정공주입층/정공수송층/발광층/전자수송층/캐소드(6) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode
(7) 애노드/정공주입층/정공수송층/발광층/전자수송층/전자주입층/캐소드(7) anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode
(8) 애노드/정공주입층/정공버퍼층/정공수송층/발광층/전자수송층/캐소드(8) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode
(9) 애노드/정공주입층/정공버퍼층/정공수송층/발광층/전자수송층/전자주입층 /캐소드(9) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode
(10) 애노드/ 정공수송층/전자차단층/발광층/전자수송층/캐소드(10) Anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode
(11) 애노드/ 정공수송층/전자차단층/발광층/전자수송층/전자주입층/캐소드(11) Anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode
(12) 애노드/정공주입층/정공수송층/전자차단층/발광층/전자수송층/캐소드(12) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode
(13) 애노드/정공주입층/정공수송층/전자차단층/발광층/전자수송층/전자주입층/캐소드(13) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode
(14) 애노드/정공수송층/발광층/정공차단층/전자수송층/캐소드(14) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode
(15) 애노드/정공수송층/발광층/정공차단층/전자수송층/전자주입층/캐소드(15) Anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode
(16) 애노드/정공주입층/정공수송층/발광층/정공차단층/전자수송층/캐소드(16) Anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode
(17) 애노드/정공주입층/정공수송층/발광층/정공차단층/전자수송층/전자주입층/캐소드(17) Anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode
(18) 애노드/정공주입층/정공수송층/전자차단층/발광층/정공차단층/전자수송 및 주입층/캐소드(18) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron transport and injection layer / cathode
본 명세서의 유기 발광 소자의 구조는 도 1 내지 도 3에 나타낸 것과 같은 구조를 가질 수 있으나, 이에만 한정되는 것은 아니다.The structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1 to 3 , but is not limited thereto.
도 1은 기판(1), 애노드(2), 발광층(6) 및 캐소드(10)가 순차적으로 적층된 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화합물은 상기 발광층(6)에 포함될 수 있다.1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, a light emitting layer 6, and a cathode 10 are sequentially stacked. In this structure, the compound may be included in the light emitting layer (6).
도 2는 기판(1), 애노드(2), 정공주입층(3), 정공수송층(4), 전자차단층(5), 발광층(6), 정공차단층(7), 전자수송층(8), 전자주입층(9) 및 캐소드(10)가 순차적으로 적층된 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화합물은 정공주입층(3), 정공수송층(4), 전자차단층(5), 발광층(6), 정공차단층(7), 전자수송층(8) 또는 전자주입층(9)에 포함될 수 있다.2 shows a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, a hole blocking layer 7, and an electron transport layer 8 , shows an example of an organic light emitting device in which an electron injection layer 9 and a cathode 10 are sequentially stacked. In such a structure, the compound is a hole injection layer (3), a hole transport layer (4), an electron blocking layer (5), a light emitting layer (6), a hole blocking layer (7), an electron transport layer (8) or an electron injection layer. (9) can be included.
도 3은 기판(1), 애노드(2), 정공주입층(3), 정공수송층(4), 전자차단층(5), 발광층(6), 정공차단층(7), 전자수송 및 주입층(11) 및 캐소드(10)가 순차적으로 적층된 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서, 상기 화합물은 정공주입층(3), 정공수송층(4), 전자차단층(5), 발광층(6), 정공차단층(7) 또는 전자수송 및 주입층(11)에 포함될 수 있다.Figure 3 is a substrate (1), anode (2), hole injection layer (3), hole transport layer (4), electron blocking layer (5), light emitting layer (6), hole blocking layer (7), electron transport and injection layer 11 and a cathode 10 are sequentially stacked. In this structure, the compound is applied to the hole injection layer 3, the hole transport layer 4, the electron blocking layer 5, the light emitting layer 6, the hole blocking layer 7 or the electron transport and injection layer 11. can be included
본 명세서의 일 실시상태에 있어서, 상기 전자차단층과 발광층은 인접하게 구비될 수 있다. 예컨대, 상기 전자차단층과 발광층은 물리적으로 접하여 구비될 수 있다.In one embodiment of the present specification, the electron blocking layer and the light emitting layer may be provided adjacently. For example, the electron blocking layer and the light emitting layer may be provided in physical contact with each other.
본 명세서의 일 실시상태에 있어서, 상기 정공수송층과 전자차단층은 인접하게 구비될 수 있다. 예컨대, 상기 정공수송층과 전자차단층은 물리적으로 접하여 구비될 수 있다.In one embodiment of the present specification, the hole transport layer and the electron blocking layer may be provided adjacent to each other. For example, the hole transport layer and the electron blocking layer may be provided in physical contact with each other.
본 명세서의 유기 발광 소자는 유기물층 중 1층 이상이 상기 화합물, 즉 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. The organic light emitting device of the present specification may be manufactured with materials and methods known in the art, except that at least one layer of organic material layers includes the compound, that is, the compound represented by Chemical Formula 1.
상기 유기 발광 소자가 복수개의 유기물층을 포함하는 경우, 상기 유기물층은 동일한 물질 또는 다른 물질로 형성될 수 있다. When the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
예컨대, 본 명세서에 따른 유기 발광 소자는 스퍼터링(sputtering)이나 전자빔 증발(e-beam evaporation)과 같은 PVD(physical vapor deposition) 방법을 이용하여, 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 애노드를 형성하고, 그 위에 정공주입층, 정공수송층, 발광층, 전자차단층, 전자수송층 및 전자주입층을 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 수도 있다.For example, the organic light emitting device according to the present specification uses a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation to form a metal or conductive metal oxide or an alloy thereof on a substrate. It is prepared by depositing an anode, forming an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer thereon, and then depositing a material that can be used as a cathode thereon. It can be. In addition to this method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
상기 유기물층은 정공수송층, 정공주입층, 전자차단층, 전자수송 및 주입층, 전자수송층, 전자주입층, 정공차단층, 및 정공주입 및 수송층 중 1 층 이상을 더 포함할 수 있다.The organic material layer may further include at least one of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole injection and transport layer.
상기 유기물층은 정공주입층, 정공수송층, 정공주입 및 수송층, 전자차단층, 발광층 및 전자수송층, 전자주입층, 전자수송 및 주입층 등을 포함하는 다층 구조일 수도 있으나, 이에 한정되지 않고 단층 구조일 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 have a multilayer structure including a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, and an electron transport and injection layer, but is not limited thereto and may have a single layer structure. can In addition, the organic material layer can be formed by a solvent process other than a deposition method using various polymer materials, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or a thermal transfer method. Can be made in layers.
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; 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 for injecting holes, and the anode material is preferably a material having a high work function so that holes can be smoothly injected into the organic material layer. Specific examples of the anode material 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; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
상기 캐소드는 전자를 주입하는 전극으로, 캐소드 물질로는 통상 유기물층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 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 for injecting electrons, and it is preferable that the cathode material is a material having a small work function so as to easily inject electrons into the organic material layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; There are multi-layered materials such as LiF/Al or LiO 2 /Al, but are not limited thereto.
상기 정공주입층은 애노드로부터 발광층으로 정공의 주입을 원활하게 하는 역할을 하는 층이며, 정공 주입 물질로는 낮은 전압에서 애노드로부터 정공을 잘 주입 받을 수 있는 물질로서, 정공 주입 물질의 HOMO(highest occupied molecular orbital)가 애노드 물질의 일함수와 주변 유기물층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린(porphyrine), 올리고티오펜, 아릴아민 계열의 유기물, 헥사니트릴헥사아자트리페닐렌 계열의 유기물, 퀴나크리돈(quinacridone) 계열의 유기물, 페릴렌(perylene) 계열의 유기물, 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나, 이들에만 한정되는 것은 아니다. 정공주입층의 두께는 1 nm 내지 150 nm일 수 있다. 상기 정공주입층의 두께가 1 nm 이상이면, 정공 주입 특성이 저하되는 것을 방지할 수 있는 이점이 있고, 150 nm 이하이면, 정공주입층의 두께가 너무 두꺼워 정공의 이동을 향상시키기 위해 구동전압이 상승되는것을 방지할 수 있는 이점이 있다.The hole injection layer is a layer that serves to facilitate the injection of holes from the anode to the light emitting layer, and the hole injection material is a material that can receive holes well from the anode at a low voltage, HOMO (highest occupied) of the hole injection material molecular orbital) is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrilehexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene-based organic materials. of organic materials, anthraquinone, polyaniline, and polythiophene-based conductive polymers, but are not limited thereto. The hole injection layer may have a thickness of 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 the thickness is 150 nm or less, the thickness of the hole injection layer is too thick, so that a driving voltage is required to improve hole movement. There are advantages to preventing it from rising.
본 명세서의 일 실시상태에 있어서, 상기 정공주입층은 카바졸기를 포함하는 아릴아민 화합물과 p형 도펀트를 포함할 수 있다. 일 예에 따르면, 상기 아민 화합물은 Het101-L101-N(Ar101)(Ar102)과 같이 표시되고, Het101은 치환 또는 비치환된 카바졸기이고, L101은 직접결합 또는 치환 또는 비치환된 아릴렌기이고, Ar101 및 Ar102는 서로 같거나 상이하고, 각각 독립적으로 치환 또는 비치환된 아릴기일 수 있다. 상기 아민 화합물과 p형 도펀트는 적절한 몰비로 포함될 수 있고, 일 예에 따르면, 상기 아민 화합물과 p형 도펀트는 99.9:0.1 내지 90:10의 몰비로 포함될 수 있다.In one embodiment of the present specification, the hole injection layer may include an arylamine compound including a carbazole group and a p-type dopant. According to one example, the amine compound is represented as Het101-L101-N(Ar101)(Ar102), Het101 is a substituted or unsubstituted carbazole group, L101 is a direct bond or a substituted or unsubstituted arylene group, Ar101 and Ar102 are the same as or different from each other, and each independently may be a substituted or unsubstituted aryl group. The amine compound and the p-type dopant may be included in an appropriate molar ratio, and according to one example, the amine compound and the p-type dopant may be included in a molar ratio of 99.9:0.1 to 90:10.
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. 구체적인 예로는 아릴아민 계열의 유기물, 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. The hole transport layer may play a role of facilitating hole transport. As the hole transport material, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer, and a material having high hole mobility is suitable. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated parts.
본 명세서의 일 실시상태에 있어서, 상기 정공수송층은 카바졸기를 포함하는 아릴아민 화합물을 포함할 수 있다.In one embodiment of the present specification, the hole transport layer may include an arylamine compound including a carbazole group.
정공주입층과 정공수송층 사이에 추가로 정공버퍼층이 구비될 있으며, 당 기술분야에 알려져 있는 정공주입 또는 수송재료를 포함할 수 있다. A hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.
정공수송층과 발광층 사이에 전자차단층이 구비될 수 있다. 상기 전자차단층에는 전술한 화합물 또는 당 기술분야에 알려져 있는 재료가 사용될 수 있다.An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The above-mentioned compounds or materials known in the art may be used for the electron blocking layer.
본 명세서의 일 실시상태에 있어서, 상기 전자차단층은 본 발명 화학식 1로 표시되는 화합물을 포함할 수 있다.In one embodiment of the present specification, the electron blocking layer may include a compound represented by Formula 1 of the present invention.
상기 발광층은 적색, 녹색 또는 청색을 발광할 수 있으며, 인광 물질 또는 형광 물질로 이루어질 수 있다. 상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서, 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로는 8-히드록시-퀴놀린 알루미늄 착물(Alq3); 카르바졸 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 ray region by receiving and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); carbazole-based compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; compounds of the benzoxazole, benzthiazole and benzimidazole series; poly(p-phenylenevinylene) (PPV)-based polymers; spiro compounds; Polyfluorene, rubrene, etc., but are not limited thereto.
발광층의 호스트 재료로는 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등이 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체, 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체, 페난트렌 화합물, 플루오란텐 화합물 등이 있고, 헤테로환 함유 화합물로는 카바졸 유도체, 디벤조퓨란 유도체, 래더형 퓨란 화합물, 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다.A host material for the light emitting layer includes a condensed aromatic ring derivative or a compound containing a hetero ring. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, ladder type furan compounds, pyrimidine derivatives, etc., but are 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, 이에만 한정된 것은 아니다. 발광층이 녹색 발광을 하는 경우, 발광 도펀트로는 Ir(ppy)3(fac tris(2-phenylpyridine)iridium)와 같은 인광물질이나, Alq3(tris(8-hydroxyquinolino)aluminum)와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다. 발광층이 청색 발광을 하는 경우, 발광 도펀트로는 (4,6-F2ppy)2Irpic와 같은 인광 물질이나, spiro-DPVBi, spiro-6P, 디스틸벤젠(DSB), 디스트릴아릴렌(DSA), PFO계 고분자, PPV계 고분자와 같은 형광 물질이 사용될 수 있으나, 이에만 한정된 것은 아니다.When the light emitting layer emits red light, PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonateiridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium), PQIr (tris (1-phenylquinoline) iridium) are used as light emitting dopants. ), a phosphorescent material such as octaethylporphyrin platinum (PtOEP), or a fluorescent material such as Alq 3 (tris(8-hydroxyquinolino)aluminum), but is not limited thereto. When the light emitting layer emits green light, a phosphorescent material such as Ir(ppy) 3 (fac tris(2-phenylpyridine)iridium) or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used as the light emitting dopant. However, it is not limited thereto. When the light emitting layer emits blue light, as the light emitting dopant, a phosphorescent material such as (4,6-F2ppy) 2 Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distryarylene (DSA), Fluorescent materials such as PFO-based polymers and PPV-based polymers may be used, but are not limited thereto.
본 명세서의 일 실시상태에 있어서, 상기 발광층은 아릴기 또는 헤테로고리기가 치환된 안트라센 화합물을 호스트로서 포함하고, 아민기가 치환된 파이렌 화합물을 도펀트로서 포함할 수 있다. 일 예에 따르면, 안트라센 화합물은 9번 탄소 및 10번 탄소가 아릴기 또는 헤테로고리기로 치환된 구조일 수 있다. 상기 호스트와 도펀트는 적절한 중량비로 포함될 수 있고, 일 예에 따르면, 상기 호스트와 도펀트는 100:1 내지 100:10의 중량비로 포함될 수 있다.In one embodiment of the present specification, the light emitting layer may include an anthracene compound substituted with an aryl group or a heterocyclic group as a host and a pyrene compound substituted with an amine group as a dopant. According to one example, the anthracene compound may have a structure in which carbon 9 and carbon 10 are substituted with an aryl group or a heterocyclic group. The host and the dopant may be included in an appropriate weight ratio, and according to one example, the host and the dopant may be included in a weight ratio of 100:1 to 100:10.
전자수송층과 발광층 사이에 정공차단층이 구비될 수 있으며, 당 기술분야에 알려져 있는 재료가 사용될 수 있다.A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and materials known in the art may be used.
본 명세서의 일 실시상태에 있어서, 상기 정공차단층은 N 함유 헤테로고리기 및 플루오렌 고리를 포함한 화합물을 포함할 수 있다.In one embodiment of the present specification, the hole blocking layer may include a compound including an N-containing heterocyclic group and a fluorene ring.
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. 구체적인 예로는 상기 전술한 화합물 또는 8-히드록시퀴놀린의 Al 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본-금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자수송층의 두께는 1 nm 내지 50 nm일 수 있다. 전자수송층의 두께가 1 nm 이상이면, 전자 수송 특성이 저하되는 것을 방지할 수 있는 이점이 있고, 50 nm 이하이면, 전자수송층의 두께가 너무 두꺼워 전자의 이동을 향상시키기 위해 구동전압이 상승되는 것을 방지할 수 있는 이점이 있다.The electron transport layer may serve to facilitate electron transport. As the electron transport material, a material capable of receiving electrons from the cathode and transferring them to the light emitting layer is suitable. Specific examples include Al complexes of the aforementioned compounds or 8-hydroxyquinoline; Complexes containing Alq 3 ; organic radical compounds; hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer may have a thickness of 1 nm to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing deterioration in electron transport properties, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the increase in driving voltage to improve electron movement. There are benefits to avoiding it.
본 명세서의 일 실시상태에 있어서, 상기 전자수송층은 2개의 N 함유 헤테로고리기를 포함하는 화합물을 포함할 수 있고, n형 도펀트 또는 유기 금속 화합물을 더 포함할 수 있다. 일 예에 따르면, 상기 n형 도펀트 또는 유기 금속 화합물은 LiQ일 수 있고, 상기 2개의 N 함유 헤테로고리기를 포함하는 화합물과 상기 n형 도펀트(또는 유기 금속 화합물)는 2:8 내지 8:2, 예컨대 4:6 내지 6:4의 중량비로 포함될 수 있다.In one embodiment of the present specification, the electron transport layer may include a compound containing two N-containing heterocyclic groups, and may further include an n-type dopant or an organometallic compound. According to one example, the n-type dopant or organometallic compound may be LiQ, and the compound containing two N-containing heterocyclic groups and the n-type dopant (or organometallic compound) have a ratio of 2:8 to 8:2, For example, it may be included in a weight ratio of 4:6 to 6:4.
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, 또한, 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논, 안트라퀴노다이메탄, 다이페노퀴논, 티오피란 다이옥사이드, 옥사졸, 옥사다이아졸, 트리아졸, 이미다졸, 페릴렌테트라카복실산, 프레오레닐리덴 메탄, 안트론 등과 그들의 유도체, 금속 착체 화합물 및 함질소 5원환 유도체 등이 있으나, 이에 한정되지 않는다. The electron injection layer may serve to smoothly inject electrons. The electron injecting material has the ability to transport electrons, has an excellent electron injecting 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 also , compounds having excellent thin film forming ability are preferred. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preonylidene methane, anthrone, etc. and their derivatives, metals complex compounds and nitrogen-containing 5-membered ring derivatives, 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 compound 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)( There are o-cresolato) gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, and bis(2-methyl-8-quinolinato)(2-naphtolato)gallium. Not limited to this.
상기 정공차단층은 정공의 캐소드 도달을 저지하는 층으로, 일반적으로 정공주입층과 동일한 조건으로 형성될 수 있다. 구체적으로 옥사디아졸 유도체나 트리아졸 유도체, 페난트롤린 유도체, BCP, 알루미늄 착물 (aluminum complex) 등이 있으나, 이에 한정되지 않는다.The hole blocking layer is a layer that blocks holes from reaching the cathode, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are 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 top emission type, a bottom emission type, or a double side emission type depending on the material used.
본 명세서에 따른 유기 발광 소자는 다양한 전자 장치에 포함되어 사용될 수 있다. 예컨대, 상기 전자 장치는 디스플레이 패널, 터치 패널, 태양광 모듈, 조명 장치 등일 수 있고, 이에 한정되지 않는다.The organic light emitting device according to the present specification may be included in 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, and the like, but is not limited thereto.
이하, 본 명세서를 구체적으로 설명하기 위해 실시예를 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, examples will be described in detail in order to specifically describe the present specification. However, the embodiments according to the present specification may be modified in many different forms, and the scope of the present application is not construed as being limited to the embodiments detailed below. The embodiments of the present application are provided to more completely explain the present specification to those skilled in the art.
제조예 1Preparation Example 1
Figure PCTKR2022009772-appb-img-000037
Figure PCTKR2022009772-appb-img-000037
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), 및 화합물 a1(4.98 g, 13.43 mmol)을 Xylene 260 mL에 완전히 녹인 후 NaOtBu(1.60 g, 16.63 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.20 g, 0.38 mmol)을 넣은 후 4시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 260 mL으로 재결정하여 화합물 1(6.89 g, 수율: 69%)를 제조하였다.Compound 9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), and compound a1 (4.98 g, 13.43 mmol) was completely dissolved in 260 mL of Xylene, NaOtBu (1.60 g, 16.63 mmol) was added, and Bis ( tritert -butylphosphine) palladium (0) (0.20 g, 0.38 mmol) was added. After adding, the mixture was heated and stirred for 4 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and recrystallized with 260 mL of ethyl acetate to prepare Compound 1 (6.89 g, yield: 69%).
MS[M+H]+= 765MS[M+H] + = 765
제조예 2Preparation Example 2
Figure PCTKR2022009772-appb-img-000038
Figure PCTKR2022009772-appb-img-000038
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), 및 화합물 a2(4.98 g, 13.43 mmol)을 Xylene 260 mL에 완전히 녹인 후 NaOtBu(1.60 g, 16.63 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.20 g, 0.38 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 280 mL으로 재결정하여 화합물 2(5.57 g, 수율: 57%)를 제조하였다.Compound 9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), and compound a2 (4.98 g, 13.43 mmol) were completely dissolved in 260 mL of Xylene, NaOtBu (1.60 g, 16.63 mmol) was added, and Bis ( tritert -butylphosphine) palladium (0) (0.20 g, 0.38 mmol) was added. After adding, the mixture was heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and recrystallized with 280 mL of ethyl acetate to prepare compound 2 (5.57 g, yield: 57%).
MS[M+H]+= 765MS[M+H] + = 765
제조예 3Preparation Example 3
Figure PCTKR2022009772-appb-img-000039
Figure PCTKR2022009772-appb-img-000039
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), 및 화합물 a3(4.85 g, 13.43 mmol)을 Xylene 250 mL에 완전히 녹인 후 NaOtBu(1.60 g, 16.63 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.20 g, 0.38 mmol)을 넣은 후 4시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 250 mL으로 재결정하여 화합물 3(4.47 g, 수율: 46%)를 제조하였다.Compound 9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), and compound a3 (4.85 g, 13.43 mmol) were completely dissolved in 250 mL of Xylene, NaOtBu (1.60 g, 16.63 mmol) was added, and Bis ( tritert -butylphosphine) palladium (0) (0.20 g, 0.38 mmol) was added. After adding, the mixture was heated and stirred for 4 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and recrystallized with 250 mL of ethyl acetate to prepare compound 3 (4.47 g, yield: 46%).
MS[M+H]+= 755MS[M+H] + = 755
제조예 4Production Example 4
Figure PCTKR2022009772-appb-img-000040
Figure PCTKR2022009772-appb-img-000040
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), 및 화합물 a4(5.65 g, 13.43 mmol)을 Xylene 250 mL에 완전히 녹인 후 NaOtBu(1.31 g, 13.60 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.20 g, 0.38 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 270 mL으로 재결정하여 화합물 4(6.27 g, 수율: 60%)를 제조하였다.Compound 9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), and compound a4 (5.65 g, 13.43 mmol) were completely dissolved in 250 mL of Xylene, NaOtBu (1.31 g, 13.60 mmol) was added, and Bis ( tritert -butylphosphine) palladium (0) (0.20 g, 0.38 mmol) was added. After adding, the mixture was heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and recrystallized with 270 mL of ethyl acetate to prepare compound 4 (6.27 g, yield: 60%).
MS[M+H]+= 765MS[M+H] + = 765
제조예 5Preparation Example 5
Figure PCTKR2022009772-appb-img-000041
Figure PCTKR2022009772-appb-img-000041
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), 및 화합물 a5(3.69 g, 13.43 mmol)을 Xylene 270 mL에 완전히 녹인 후 NaOtBu(1.60 g, 16.63 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.20 g, 0.38 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 270 mL으로 재결정하여 화합물 5(4.97 g, 수율: 58%)를 제조하였다.Compound 9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), and compound a5 (3.69 g, 13.43 mmol) were completely dissolved in 270 mL of Xylene, NaOtBu (1.60 g, 16.63 mmol) was added, and Bis ( tritert -butylphosphine) palladium (0) (0.20 g, 0.38 mmol) was added. After adding, the mixture was heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and recrystallized with 270 mL of ethyl acetate to prepare compound 5 (4.97 g, yield: 58%).
MS[M+H]+= 671MS[M+H] + = 671
제조예 6Preparation Example 6
Figure PCTKR2022009772-appb-img-000042
Figure PCTKR2022009772-appb-img-000042
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), 및 화합물 a6(4.47 g, 13.43 mmol)을 Xylene 250 mL에 완전히 녹인 후 NaOtBu(1.60 g, 16.63 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.20 g, 0.38 mmol)을 넣은 후 4시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 280 mL으로 재결정하여 화합물 6(5.57 g, 수율: 60%)를 제조하였다.Compound 9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), and compound a6 (4.47 g, 13.43 mmol) were completely dissolved in 250 mL of Xylene, NaOtBu (1.60 g, 16.63 mmol) was added, and Bis ( tritert -butylphosphine) palladium (0) (0.20 g, 0.38 mmol) was added. After adding, the mixture was heated and stirred for 4 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and recrystallized with 280 mL of ethyl acetate to prepare compound 6 (5.57 g, yield: 60%).
MS[M+H]+= 729MS[M+H] + = 729
제조예 7Preparation Example 7
Figure PCTKR2022009772-appb-img-000043
Figure PCTKR2022009772-appb-img-000043
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), 및 화합물 a7(4.97 g, 13.43 mmol)을 Xylene 280 mL에 완전히 녹인 후 NaOtBu(1.60 g, 16.63 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.20 g, 0.38 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 220 mL으로 재결정하여 화합물 7(6.44 g, 수율: 66%)를 제조하였다.Compound 9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), and compound a7 (4.97 g, 13.43 mmol) were completely dissolved in 280 mL of Xylene, NaOtBu (1.60 g, 16.63 mmol) was added, and Bis ( tritert -butylphosphine) palladium (0) (0.20 g, 0.38 mmol) was added. After adding, the mixture was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and recrystallized with 220 mL of ethyl acetate to prepare compound 7 (6.44 g, yield: 66%).
MS[M+H]+= 765MS[M+H] + = 765
제조예 8Preparation Example 8
Figure PCTKR2022009772-appb-img-000044
Figure PCTKR2022009772-appb-img-000044
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), 및 화합물 a8(4.97 g, 13.43 mmol)을 Xylene 260 mL에 완전히 녹인 후 NaOtBu(1.60 g, 16.63 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.20 g, 0.38 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 270 mL으로 재결정하여 화합물 8(5.57 g, 수율: 57%)를 제조하였다.Compound 9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), and compound a8 (4.97 g, 13.43 mmol) were completely dissolved in 260 mL of Xylene, NaOtBu (1.60 g, 16.63 mmol) was added, and Bis ( tritert -butylphosphine) palladium (0) (0.20 g, 0.38 mmol) was added. After adding, the mixture was heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and recrystallized with 270 mL of ethyl acetate to prepare compound 8 (5.57 g, yield: 57%).
MS[M+H]+= 765MS[M+H] + = 765
제조예 9Preparation Example 9
Figure PCTKR2022009772-appb-img-000045
Figure PCTKR2022009772-appb-img-000045
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), 및 화합물 a9(4.16 g, 13.43 mmol)을 Xylene 250 mL에 완전히 녹인 후 NaOtBu(1.60 g, 16.63 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.20 g, 0.38 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 테트라하이드로퓨란 240 mL으로 재결정하여 화합물 9(6.13 g, 수율: 67%)를 제조하였다.Compound 9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), and compound a9 (4.16 g, 13.43 mmol) were completely dissolved in 250 mL of Xylene, NaOtBu (1.60 g, 16.63 mmol) was added, and Bis ( tritert -butylphosphine) palladium (0) (0.20 g, 0.38 mmol) was added. After adding, the mixture was heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and recrystallized with 240 mL of tetrahydrofuran to prepare compound 9 (6.13 g, yield: 67%).
MS[M+H]+= 792MS[M+H] + = 792
제조예 10Preparation Example 10
Figure PCTKR2022009772-appb-img-000046
Figure PCTKR2022009772-appb-img-000046
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), 및 화합물 a10(4.16 g, 13.43 mmol)을 Xylene 250 mL에 완전히 녹인 후 NaOtBu(1.60 g, 16.63 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.20 g, 0.38 mmol)을 넣은 후 3시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 250 mL으로 재결정하여 화합물 10(5.87 g, 수율: 64%)를 제조하였다.Compound 9-(4'-chloro-[1,1':3',1''-terphenyl]-3-yl)-9H-carbazole (5.50 g, 12.79 mmol), and compound a10 (4.16 g, 13.43 mmol) were completely dissolved in 250 mL of Xylene, NaOtBu (1.60 g, 16.63 mmol) was added, and Bis ( tritert -butylphosphine) palladium (0) (0.20 g, 0.38 mmol) was added. After adding, the mixture was heated and stirred for 3 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and recrystallized with 250 mL of ethyl acetate to prepare Compound 10 (5.87 g, yield: 64%).
MS[M+H]+= 765MS[M+H] + = 765
제조예 11Preparation Example 11
Figure PCTKR2022009772-appb-img-000047
Figure PCTKR2022009772-appb-img-000047
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 99-(4'-chloro-3'-(naphthalen-1-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole (4.50 g, 9.38 mmol), 및 화합물 a11(3.40 g, 9.84 mmol)을 Xylene 250 mL에 완전히 녹인 후 NaOtBu(1.17 g, 12.19 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.14 g, 0.28 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 260 mL으로 재결정하여 화합물 11(4.92 g, 수율: 67%)를 제조하였다.Compound 99-(4'-chloro-3'-(naphthalen-1-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole (4.50 g, 9.38 mmol) and compound a11 (3.40 g, 9.84 mmol) were completely dissolved in 250 mL of Xylene, NaOtBu (1.17 g, 12.19 mmol) was added, and Bis(tri- tert -butylphosphine) palladium(0)(0.14 g, After adding 0.28 mmol), the mixture was heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and recrystallized with 260 mL of ethyl acetate to prepare Compound 11 (4.92 g, yield: 67%).
MS[M+H]+= 789MS[M+H] + = 789
제조예 12Preparation Example 12
Figure PCTKR2022009772-appb-img-000048
Figure PCTKR2022009772-appb-img-000048
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(4'-chloro-[1,1':3',1'':3'',1'''-quaterphenyl]-3-yl)-9H-carbazole (4.50 g, 8.89 mmol), 및 화합물 a12(2.29 g, 9.34 mmol)을 Xylene 250 mL에 완전히 녹인 후 NaOtBu(1.11g, 11.56 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.14 g, 0.27 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 210 mL으로 재결정하여 화합물 12(3.78 g, 수율: 59%)를 제조하였다.Compound 9-(4'-chloro-[1,1':3',1'':3'',1'''-quaterphenyl]-3-yl)-9H- was added to a 500 mL round bottom flask under a nitrogen atmosphere. After completely dissolving carbazole (4.50 g, 8.89 mmol) and compound a12 (2.29 g, 9.34 mmol) in 250 mL of Xylene, NaOtBu (1.11 g, 11.56 mmol) was added, and Bis (tri- tert -butylphosphine) palladium (0 ) (0.14 g, 0.27 mmol) was added and heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and recrystallized with 210 mL of ethyl acetate to prepare Compound 12 (3.78 g, yield: 59%).
MS[M+H]+= 715MS[M+H] + = 715
제조예 13Preparation Example 13
Figure PCTKR2022009772-appb-img-000049
Figure PCTKR2022009772-appb-img-000049
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(4'-chloro-3'-(phenanthren-9-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole (4.50 g, 8.49 mmol), 및 화합물 a13(2.86 g, 8.92 mmol)을 Xylene 230 mL에 완전히 녹인 후 NaOtBu(1.06 g, 11.04 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.13 g, 0.25 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 테트라하이드로퓨란 170 mL으로 재결정하여 화합물 13(4.55 g, 수율: 66%)를 제조하였다.Compound 9-(4'-chloro-3'-(phenanthren-9-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole (4.50 g, 8.49 mmol) and compound a13 (2.86 g, 8.92 mmol) were completely dissolved in 230 mL of Xylene, NaOtBu (1.06 g, 11.04 mmol) was added, and Bis(tri- tert -butylphosphine) palladium(0)(0.13 g, After adding 0.25 mmol), the mixture was heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and recrystallized with 170 mL of tetrahydrofuran to prepare compound 13 (4.55 g, yield: 66%).
MS[M+H]+= 816MS[M+H] + = 816
제조예 14Preparation Example 14
Figure PCTKR2022009772-appb-img-000050
Figure PCTKR2022009772-appb-img-000050
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(4'-chloro-3'-(naphthalen-2-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole (4.50 g, 9.38 mmol), 및 화합물 a14(2.90 g, 9.84 mmol)을 Xylene 250 mL에 완전히 녹인 후 NaOtBu(1.17 g, 12.19 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.14 g, 0.28 mmol)을 넣은 후 6시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 240 mL으로 재결정하여 화합물 14(3.77 g, 수율: 54%)를 제조하였다.Compound 9-(4'-chloro-3'-(naphthalen-2-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole (4.50 g, 9.38 mmol) and compound a14 (2.90 g, 9.84 mmol) were completely dissolved in 250 mL of Xylene, NaOtBu (1.17 g, 12.19 mmol) was added, and Bis (tri- tert -butylphosphine) palladium (0) (0.14 g, After adding 0.28 mmol), the mixture was heated and stirred for 6 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to prepare Compound 14 (3.77 g, yield: 54%).
MS[M+H]+= 739MS[M+H] + = 739
제조예 15Preparation Example 15
Figure PCTKR2022009772-appb-img-000051
Figure PCTKR2022009772-appb-img-000051
질소 분위기에서 500 mL 둥근 바닥 플라스크에 화합물 9-(4'-chloro-3'-(dibenzo[b,d]furan-3-yl)-[1,1'-biphenyl]-3-yl)-9H-carbazole (4.50 g, 8.65 mmol), 및 화합물 a15(2.92 g, 9.09 mmol)을 Xylene 250 mL에 완전히 녹인 후 NaOtBu(1.08 g, 11.25 mmol)을 첨가하고, Bis(tri-tert-butylphosphine) palladium(0)(0.13 g, 0.26 mmol)을 넣은 후 5시간 동안 가열 교반하였다. 상온으로 온도를 낮추고 filter하여 base를 제거한 후 Xylene을 감압농축 시키고 에틸아세테이트 240 mL으로 재결정하여 화합물 15(4.59 g, 수율: 66%)를 제조하였다.Compound 9-(4'-chloro-3'-(dibenzo[b,d]furan-3-yl)-[1,1'-biphenyl]-3-yl)-9H in a 500 mL round bottom flask under nitrogen atmosphere After completely dissolving -carbazole (4.50 g, 8.65 mmol) and compound a15 (2.92 g, 9.09 mmol) in 250 mL of Xylene, NaOtBu (1.08 g, 11.25 mmol) was added, and Bis (tri- tert -butylphosphine) palladium ( After adding 0) (0.13 g, 0.26 mmol), the mixture was heated and stirred for 5 hours. After lowering the temperature to room temperature and filtering to remove the base, Xylene was concentrated under reduced pressure and recrystallized with 240 mL of ethyl acetate to prepare Compound 15 (4.59 g, yield: 66%).
MS[M+H]+= 805MS[M+H] + = 805
실시예 1-1Example 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 ITO (indium tin oxide) to a thickness of 1,000 Å was put in distilled water in which detergent was dissolved and washed with ultrasonic waves. At this time, a Fischer Co. product was used as the detergent, and distilled water filtered through a second filter of a Millipore Co. product was used as the distilled water. After washing the ITO for 30 minutes, ultrasonic cleaning was performed twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and transported to a plasma cleaner. In addition, after cleaning the substrate for 5 minutes using oxygen plasma, the substrate was transferred to a vacuum deposition machine.
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 상기 제조예 1에서 제조한 화합물 1을 진공 증착하여 전자차단층을 형성하였다. 이어서, 상기 전자차단층 위에 막 두께 200Å으로 하기 화학식 BH로 표시되는 화합물 및 하기 화학식 BD로 표시되는 화합물을 25:1의 중량비로 진공증착하여 발광층을 형성하였다. 상기 발광층 위에 막 두께 50Å으로 하기 화학식 HB1으로 표시되는 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. A hole injection layer was formed by thermally vacuum-depositing the following compound HI1 and the following compound HI2 to a thickness of 100 Å in a ratio of 98:2 (molar ratio) on the ITO transparent electrode prepared as described above. A hole transport layer was formed by vacuum depositing a compound (1150 Å) represented by Chemical Formula HT1 on the hole injection layer. Then, the compound 1 prepared in Preparation Example 1 was vacuum deposited to form a film thickness of 50 Å on the hole transport layer to form an electron blocking layer. Subsequently, a light emitting layer was formed by vacuum depositing a compound represented by Chemical Formula BH and a compound represented by Chemical Formula BD at a weight ratio of 25:1 to a film thickness of 200 Å on the electron blocking layer. A hole blocking layer was formed on the light emitting layer by vacuum depositing a compound represented by Chemical Formula HB1 to a film thickness of 50 Å. Subsequently, a compound represented by Chemical Formula ET1 and a compound represented by Chemical Formula LiQ were vacuum deposited at a weight ratio of 1:1 on the hole blocking layer to form an electron injection and transport layer with a thickness of 310 Å. A negative electrode 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 PCTKR2022009772-appb-img-000052
Figure PCTKR2022009772-appb-img-000052
상기의 과정에서 유기물의 증착속도는 0.4 내지 0.7 Å/sec를 유지하였고, 음극의 리튬플로라이드는 0.3 Å/sec, 알루미늄은 2 Å/sec의 증착 속도를 유지하였으며, 증착시 진공도는 2×10-7 내지 5×10-6 torr를 유지하여, 유기 발광 소자를 제작하였다.In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 Å/sec, the deposition rate of lithium fluoride on the negative electrode was 0.3 Å/sec, and the deposition rate of aluminum was 2 Å/sec, and the vacuum level during deposition was 2×10 Maintaining -7 to 5×10 -6 torr, an organic light emitting device was fabricated.
실시예 1-2 내지 실시예 1-15Examples 1-2 to 1-15
상기 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 in Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1.
Figure PCTKR2022009772-appb-img-000053
Figure PCTKR2022009772-appb-img-000053
비교예 1-1 내지 1-5Comparative Examples 1-1 to 1-5
상기 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 EB2, EB3, EB4 및 EB5 의 화합물을 하기와 같다.An organic light emitting device was manufactured in the same manner as in Example 1-1, except that the compound shown in Table 1 was used instead of Compound 1. The compounds of EB2, EB3, EB4 and EB5 used in Table 1 are as follows.
Figure PCTKR2022009772-appb-img-000054
Figure PCTKR2022009772-appb-img-000054
실험예 1Experimental Example 1
상기 실시예 및 비교예에서 제조한 유기 발광 소자에 10mA/cm2의 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 a current of 10 mA/cm 2 was applied to the organic light emitting devices prepared in the above Examples and Comparative Examples, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T95 means the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.
화합물
(전자차단층)compound
(electronic blocking layer) 		전압
(V
10mA/cm2)Voltage
(V
10 mA/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 4.514.51 6.616.61 (0.145, 0.045)(0.145, 0.045) 265265
실시예 1-2Example 1-2 화합물 2compound 2 4.534.53 6.636.63 (0.144, 0.044)(0.144, 0.044) 260260
실시예 1-3Example 1-3 화합물 3compound 3 4.564.56 6.646.64 (0.146, 0.045)(0.146, 0.045) 265265
실시예 1-4Example 1-4 화합물 4compound 4 4.574.57 6.696.69 (0.145, 0.044)(0.145, 0.044) 260260
실시예 1-5Example 1-5 화합물 5compound 5 4.554.55 6.696.69 (0.144, 0.044)(0.144, 0.044) 265265
실시예 1-6Example 1-6 화합물 6compound 6 4.514.51 6.656.65 (0.146, 0.045)(0.146, 0.045) 265265
실시예 1-7Examples 1-7 화합물 7compound 7 4.374.37 6.816.81 (0.145, 0.044)(0.145, 0.044) 280280
실시예 1-8Examples 1-8 화합물 8compound 8 4.394.39 6.846.84 (0.146, 0.045)(0.146, 0.045) 285285
실시예 1-9Examples 1-9 화합물 9compound 9 4.34.3 6.836.83 (0.145, 0.046)(0.145, 0.046) 280280
실시예 1-10Examples 1-10 화합물 10compound 10 4.494.49 6.596.59 (0.145, 0.046)(0.145, 0.046) 270270
실시예 1-11Example 1-11 화합물 11compound 11 4.604.60 6.536.53 (0.145, 0.046)(0.145, 0.046) 255255
실시예 1-12Examples 1-12 화합물 12compound 12 4.644.64 6.566.56 (0.145, 0.046)(0.145, 0.046) 240240
실시예 1-13Examples 1-13 화합물 13compound 13 4.634.63 6.536.53 (0.145, 0.046)(0.145, 0.046) 245245
실시예 1-14Examples 1-14 화합물 14compound 14 4.624.62 6.506.50 (0.145, 0.046)(0.145, 0.046) 250250
실시예 1-15Examples 1-15 화합물 15compound 15 4.604.60 6.516.51 (0.145, 0.046)(0.145, 0.046) 255255
비교예 1-1Comparative Example 1-1 EB1EB1 5.135.13 6.056.05 (0.145, 0.046)(0.145, 0.046) 130130
비교예 1-2Comparative Example 1-2 EB2EB2 4.964.96 5.875.87 (0.146, 0.044)(0.146, 0.044) 155155
비교예 1-3Comparative Example 1-3 EB3EB3 5.065.06 6.126.12 (0.144, 0.046)(0.144, 0.046) 135135
비교예 1-4Comparative Example 1-4 EB4EB4 4.744.74 5.985.98 (0.145, 0.047)(0.145, 0.047) 150150
비교예 1-5Comparative Example 1-5 EB5EB5 5.335.33 5.845.84 (0.144, 0.046)(0.144, 0.046) 160160
상기 표 1에 나타난 바와 같이, 본 발명의 화합물을 전자차단층으로 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 an electron blocking layer exhibited excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device.
실시예 1-1 내지 1-15에서 meta-바이페닐렌기 중 아민에 연결된 페닐렌기에 추가의 치환기 R2가 결합된 물질을 전자차단층으로 사용하였을 때 저전압, 고효율, 장수명의 특성을 보이는 것을 알 수 있었다.In Examples 1-1 to 1-15, it can be seen that when a material in which an additional substituent R2 is bonded to an amine-linked phenylene group among meta-biphenylene groups is used as an electron blocking layer, it exhibits characteristics of low voltage, high efficiency, and long lifespan. there was.
비교예 1-1 및 1-5과 같이 본 발명의 meta-바이페닐렌기와는 상이한 구조를 갖는 링커를 포함하거나, 아민기가 3환의 아릴기인 페난트레닐기 또는 플루오레닐기로 치환된 비교예 화합물 EB1 내지 EB5의 물질을 사용한 경우, 전압이 상승하고, 효율이 저하되었으며, 특히 안정성(수명)이 크게 저하되는 결과를 나타내었다.As in Comparative Examples 1-1 and 1-5, Comparative Example Compound EB1 comprising a linker having a structure different from the meta-biphenylene group of the present invention or having an amine group substituted with a phenanthrenyl group or fluorenyl group, which is a tricyclic aryl group. In the case of using the materials of from EB5 to EB5, the voltage increased, the efficiency decreased, and in particular, the stability (lifetime) was greatly reduced.
이상을 통해 본 발명의 바람직한 실시예(전자차단층)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 (electron blocking layer) of the present invention has been described above, the present invention is not limited thereto and can be modified and implemented in various ways within the scope of the claims and detailed description of the invention, and this also belongs to the category of invention.

Claims (10)

  1. 하기 화학식 1로 표시되는 화합물:A compound represented by Formula 1 below:
    [화학식 1][Formula 1]
    Figure PCTKR2022009772-appb-img-000055
    Figure PCTKR2022009772-appb-img-000055
    상기 화학식 1에 있어서,In Formula 1,
    L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 단환으로 이루어진 아릴렌기; 또는 2환의 아릴렌기이고,L1 and L2 are the same as or different from each other, and are each independently a direct bond; An arylene group consisting of a monocycle; Or a bicyclic arylene group,
    Ar1 및 Ar2은 서로 같거나 상이하고, 각각 독립적으로 단환으로 이루어진 아릴기; 2환의 아릴기; 및 헤테로고리기로 이루어진 군에서 선택된 하나이거나, 상기 군에서 선택된 2 이상의 기가 연결된 기이고,Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic aryl group; a bicyclic aryl group; And one selected from the group consisting of a heterocyclic group, or a group in which two or more groups selected from the group are connected,
    R1은 수소; 중수소; 치환 또는 비치환된 알킬기; 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이거나, 인접한 기와 서로 결합하여 치환 또는 비치환된 고리를 형성하고,R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or bonded to adjacent groups to form a substituted or unsubstituted ring;
    R2는 치환 또는 비치환된 아릴기; 또는 치환 또는 비치환된 헤테로고리기이고,R2 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
    a는 0 내지 8의 정수이고, a가 2 이상인 경우, 2 이상의 R1은 서로 같거나 상이하다.a is an integer from 0 to 8, and when a is 2 or more, 2 or more R1s are the same as or different from each other.
  2. 청구항 1에 있어서, 상기 R2는 치환 또는 비치환된 페닐기; 치환 또는 비치환된 바이페닐기; 치환 또는 비치환된 나프틸기; 치환 또는 비치환된 페난트레닐기; 치환 또는 비치환된 플루오레닐기; 치환 또는 비치환된 디벤조퓨란기; 또는 치환 또는 비치환된 디벤조티오펜기인 것인 화합물.The method according to claim 1, wherein R2 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofuran group; Or a compound that is a substituted or unsubstituted dibenzothiophene group.
  3. 청구항 1에 있어서, 상기 화학식 1은 하기 화학식 1-1 내지 1-5 중 어느 하나로 표시되는 것인 화합물:The compound according to claim 1, wherein Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-5:
    [화학식 1-1][Formula 1-1]
    Figure PCTKR2022009772-appb-img-000056
    Figure PCTKR2022009772-appb-img-000056
    [화학식 1-2][Formula 1-2]
    Figure PCTKR2022009772-appb-img-000057
    Figure PCTKR2022009772-appb-img-000057
    [화학식 1-3][Formula 1-3]
    Figure PCTKR2022009772-appb-img-000058
    Figure PCTKR2022009772-appb-img-000058
    [화학식 1-4][Formula 1-4]
    Figure PCTKR2022009772-appb-img-000059
    Figure PCTKR2022009772-appb-img-000059
    [화학식 1-5][Formula 1-5]
    Figure PCTKR2022009772-appb-img-000060
    Figure PCTKR2022009772-appb-img-000060
    상기 화학식 1-1 내지 1-5에 있어서, L1, L2, Ar1, Ar2, R1 및 a의 정의는 상기 화학식 1에서 정의한 바와 같고,In Formulas 1-1 to 1-5, the definitions of L1, L2, Ar1, Ar2, R1 and a are as defined in Formula 1,
    X는 O; 또는 S이다.X is O; or S.
  4. 청구항 1에 있어서, 상기 Ar1 및 Ar2은 서로 같거나 상이하고, 각각 독립적으로 나프틸기로 치환 또는 비치환된 페닐기; 나프틸기로 치환 또는 비치환된 바이페닐기; 터페닐기; 쿼터페닐기; 페닐기 또는 바이페닐기로 치환 또는 비치환된 나프틸기; 디벤조퓨란기; 또는 디벤조티오펜기인 것인 화합물.The method according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a naphthyl group; A biphenyl group unsubstituted or substituted with a naphthyl group; terphenyl group; Quarter phenyl group; a naphthyl group unsubstituted or substituted with a phenyl group or a biphenyl group; Dibenzofuran group; Or a compound that is a dibenzothiophene group.
  5. 청구항 1에 있어서, 상기 L1 및 L2는 서로 같거나 상이하고, 각각 독립적으로 직접결합; 단환으로 이루어진 탄소수 6 내지 30의 아릴렌기; 또는 2환의 아릴렌기이고,The method according to claim 1, wherein the L1 and L2 are the same as or different from each other, each independently a direct bond; A monocyclic arylene group having 6 to 30 carbon atoms; Or a bicyclic arylene group,
    상기 Ar1 및 Ar2은 서로 같거나 상이하고, 각각 독립적으로 단환으로 이루어진 탄소수 6 내지 30의 아릴기; 2환의 아릴기; 또는 탄소수 2 내지 30의 O 또는 S 함유 헤테로고리기이고,Ar1 and Ar2 are the same as or different from each other, and each independently represents a monocyclic aryl group having 6 to 30 carbon atoms; a bicyclic aryl group; Or an O or S-containing heterocyclic group having 2 to 30 carbon atoms,
    상기 R1은 수소; 또는 중수소이고,R1 is hydrogen; or deuterium;
    상기 R2는 탄소수 6 내지 30의 아릴기; 또는 탄소수 2 내지 30의 O 또는 S 함유 헤테로고리기인 것인 화합물.R2 is an aryl group having 6 to 30 carbon atoms; Or a compound that is a heterocyclic group containing O or S having 2 to 30 carbon atoms.
  6. 청구항 1에 있어서, 상기 화학식 1은 하기 화합물 중 어느 하나로 표시되는 것인 화합물:The compound according to claim 1, wherein Formula 1 is represented by any one of the following compounds:
    Figure PCTKR2022009772-appb-img-000061
    Figure PCTKR2022009772-appb-img-000061
    Figure PCTKR2022009772-appb-img-000062
    Figure PCTKR2022009772-appb-img-000062
    Figure PCTKR2022009772-appb-img-000063
    Figure PCTKR2022009772-appb-img-000063
    Figure PCTKR2022009772-appb-img-000064
    Figure PCTKR2022009772-appb-img-000064
    Figure PCTKR2022009772-appb-img-000065
    Figure PCTKR2022009772-appb-img-000065
    Figure PCTKR2022009772-appb-img-000066
    Figure PCTKR2022009772-appb-img-000066
    Figure PCTKR2022009772-appb-img-000067
    Figure PCTKR2022009772-appb-img-000067
    Figure PCTKR2022009772-appb-img-000068
    Figure PCTKR2022009772-appb-img-000068
    Figure PCTKR2022009772-appb-img-000069
    Figure PCTKR2022009772-appb-img-000069
    Figure PCTKR2022009772-appb-img-000070
    Figure PCTKR2022009772-appb-img-000070
    Figure PCTKR2022009772-appb-img-000071
    Figure PCTKR2022009772-appb-img-000071
    Figure PCTKR2022009772-appb-img-000072
    .
    Figure PCTKR2022009772-appb-img-000072
    .
  7. 애노드; 캐소드; 및 상기 애노드와 상기 캐소드 사이에 구비된 1 층 이상의 유기물층을 포함하는 유기 발광 소자로서, 상기 유기물층 중 1 층 이상은 청구항 1 내지 6 중 어느 한 항에 따른 화합물을 포함하는 것인 유기 발광 소자.anode; cathode; and one or more organic material layers provided between the anode and the cathode, wherein at least one of the organic material layers includes the compound according to any one of claims 1 to 6.
  8. 청구항 7에 있어서,The method of claim 7,
    상기 유기물층은 정공주입층, 정공수송층, 또는 정공 주입 및 수송층을 포함하고, 상기 정공주입층, 정공수송층, 또는 정공 주입 및 수송층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic material layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, wherein the hole injection layer, the hole transport layer, or the hole injection and transport layer includes the compound.
  9. 청구항 7에 있어서,The method of claim 7,
    상기 유기물층은 전자차단층을 포함하고, 상기 전자차단층은 상기 화합물을 포함하는 것인 유기 발광 소자.The organic material layer includes an electron blocking layer, and the electron blocking layer includes the compound.
  10. 청구항 7에 있어서,The method of claim 7,
    상기 유기물층은 정공수송층, 정공주입층, 전자차단층, 정공주입 및 수송층, 발광층, 전자수송층, 전자주입층, 정공차단층 및 전자수송 및 주입층 중 1층 이상을 더 포함하는 것인 유기 발광 소자.The organic material layer further comprises at least one layer of a hole transport layer, a hole injection layer, an electron blocking layer, a hole injection and transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer. .
PCT/KR2022/009772 2021-08-23 2022-07-06 Compound and organic light-emitting device comprising same WO2023027327A1 (en)

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