WO2023027327A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant 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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Korean (ko)
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차용범
문현진
이성재
이형진
조우진
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주식회사 엘지화학
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Priority to CN202280009576.7A priority Critical patent/CN116783186A/zh
Publication of WO2023027327A1 publication Critical patent/WO2023027327A1/fr

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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

La présente invention concerne un composé représenté par la formule chimique 1, et un dispositif électroluminescent organique comprenant le composé.
PCT/KR2022/009772 2021-08-23 2022-07-06 Composé et dispositif électroluminescent organique le comprenant WO2023027327A1 (fr)

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