Compounds and organic light emitting devices comprising the same

Abstract

The present specification provides a compound represented by Chemical Formula 1 and an organic light emitting device including the same.

Description

Technical Field

[0001] This application claims priority to Korean Patent Application No. 10-2021-0102914, filed with the Korean Patent Office on August 5, 2021, the entire contents of which are incorporated herein by reference.

[0002] This specification relates to compounds and organic light-emitting devices containing them. Background Technology

[0003] Organic light emission (OLED) typically refers to the phenomenon of converting electrical energy into light energy using organic materials. OLED devices generally have a structure comprising an anode and a cathode, with an organic layer between them. To improve the efficiency and stability of OLEDs, the organic layer is often formed by a multilayer structure composed of different materials; for example, it can consist of a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. In such an OLED structure, if a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode, and electrons are injected into the organic layer from the cathode. When the injected holes and electrons meet, they form excitons. When these excitons re-enter the ground state, they emit light.

[0004] There is a continuous demand for the development of new materials for organic light-emitting devices as described above.

[0005] Existing technical documents

[0006] (Patent Document 1) Korean Patent Publication No. 10-2011-0084798 Summary of the Invention

[0007] Technical issues

[0008] This specification provides compounds and organic light-emitting devices containing them.

[0009] Solution to the problem

[0010] One embodiment of this specification provides a compound represented by the following chemical formula 1.

[0011] [Chemical Formula 1]

[0012]

[0013] In the above chemical formula 1,

[0014] L1 and L2 may be the same or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group.

[0015] Ar1 and Ar2 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0016] R1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring formed by combining with adjacent groups.

[0017] R2 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0018] a is an integer from 0 to 8. When a is 2 or more, two or more R1s are the same or different from each other.

[0019] In addition, one embodiment of this specification provides an organic light-emitting device, which includes: an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers contain a compound represented by the above chemical formula 1.

[0020] Invention Effects

[0021] The compounds described in this specification can be used as materials for the organic layer of organic light-emitting devices. The compounds according to at least one embodiment of this specification can achieve improved efficiency, lower driving voltage, and / or improved lifetime characteristics in organic light-emitting devices. In particular, the compounds described in this specification can be used as materials for hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection. Furthermore, compared to existing organic light-emitting devices, they exhibit lower driving voltage, higher efficiency, and / or longer lifetime. Attached Figure Description

[0022] Figure 1 The illustration 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 stacked in sequence.

[0023] Figure 2 The illustration shows an example of an organic light-emitting device in which 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, an electron transport layer 8, an electron injection layer 9, and a cathode 10 are stacked in sequence.

[0024] Figure 3 The illustration shows an example of an organic light-emitting device comprising 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, an electron transport and injection layer 11, and a cathode 10, which are stacked in sequence.

[0025] [Symbol Explanation]

[0026] 1: Substrate

[0027] 2: Anode

[0028] 3: Hole injection layer

[0029] 4: Hole transport layer

[0030] 5: Electron blocking layer

[0031] 6: Emissive layer

[0032] 7: Cavity barrier layer

[0033] 8: Electron transport layer

[0034] 9: Electron injection layer

[0035] 10: Cathode

[0036] 11: Electron transport and injection layer Detailed Implementation

[0037] The following is a more detailed description of this instruction manual.

[0038] In this specification, when a part is indicated to "include / contain" a certain component, unless otherwise stated, it means that other components may be included, rather than excluded.

[0039] In this specification, when it is stated that a component is "on" another component, it includes not only the case where one component is connected to another component, but also the case where there are other components between the two components.

[0040] In this specification, " "" or dashed lines indicate the position where it is combined with a chemical formula or compound.

[0041] Examples of substituents in this specification are described below, but are not limited thereto.

[0042] The term "substitution" refers to the replacement of hydrogen atoms on carbon atoms in a compound with other substituents. There is no limitation on the position of substitution, as long as the hydrogen atom can be substituted, that is, the position where the substituent can be substituted. When more than two substituents are substituted, the two or more substituents can be the same or different from each other.

[0043] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, halogen groups, nitrile (-CN), nitro, hydroxyl, alkyl, cycloalkyl, alkoxy, phosphine oxide, aryloxy, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl, alkenyl, silyl, boron, amino, aryl, or heterocyclic groups, or substituted by two or more substituents linked together as exemplified above, or without any substituents. For example, "substituents linked together as 2 or more substituents" can be biphenyl. That is, biphenyl can be aryl, or it can be interpreted as a substituent formed by two phenyl groups linked together.

[0044] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, halogen group, nitrile group, nitro group, hydroxyl group, amino group, silyl group, boron group, alkoxy group, aryloxy group, alkyl group, cycloalkyl group, aryl group, and heterocyclic group, or substituted by two or more substituents linked together from the substituents exemplified above, or not having any substituents.

[0045] In this specification, the term "substituted or unsubstituted" means substituted by one or more substituents selected from deuterium, alkyl, aryl, and heterocyclic groups, or substituted by a substituent formed by linking two or more substituents of the substituents exemplified above, or having no substituents.

[0046] Examples of the substituents mentioned above are given below, but are not limited thereto.

[0047] Examples of halogen groups in this specification include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0048] In this specification, the silyl group can be composed of -SiY a Y b Y c The chemical formula of the above Y represents a Y b and Y c Each can be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the aforementioned silyl groups include trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but are not limited to these.

[0049] In this specification, the boron group can be represented by -BY d Y e The chemical formula of the above Y represents d and Y eEach can be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the aforementioned boron groups include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, and phenylboryl, but are not limited to these.

[0050] In this specification, the alkyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to yet another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, etc., but are not limited to these.

[0051] In this specification, the above description of alkyl groups applies, except when aryl alkyl groups are substituted with aryl groups.

[0052] In this specification, the alkoxy group can be straight-chain, branched, or cyclic. The number of carbon atoms in the alkoxy group is not particularly limited, but preferably 1 to 20. Specifically, it can be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, etc., but is not limited to these.

[0053] The alkyl, alkoxy, and other substituents containing alkyl moiety described in this specification include both straight-chain and branched forms.

[0054] In this specification, the alkenyl group can be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, styryl, etc., but are not limited to these.

[0055] In this specification, the alkynyl group is a substituent containing a triple bond between carbon atoms, and can be straight-chain or branched. The number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkynyl group has 2 to 20 carbon atoms. According to another embodiment, the alkynyl group has 2 to 10 carbon atoms.

[0056] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group with 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., are used, but are not limited to these.

[0057] In this specification, the amino group is -NH2, and the amino group may be substituted with alkyl, aryl, heterocyclic, alkenyl, cycloalkyl, or combinations thereof. The number of carbon atoms in the substituted amino group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the number of carbon atoms in the amino group is 1 to 20. According to another embodiment, the number of carbon atoms in the amino group is 1 to 10. Specific examples of substituted amino groups include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, 9,9-dimethylfluorenylphenylamino, pyridylphenylamino, diphenylamino, phenylpyridylamino, naphthylamino, biphenylamino, anthraceneamino, dibenzofuranylphenylamino, 9-methylanthraylamino, diphenylamino, phenylnaphthylamino, xylylamino, phenyltolylamino, diphenylamino, etc., but are not limited to these.

[0058] In this specification, the aryl group is not particularly limited, but is preferably an aryl group with 6 to 60 carbon atoms, and can be a monocyclic aryl or polycyclic aryl. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. Regarding the aforementioned aryl group, as a monocyclic aryl group, it can be phenyl, biphenyl, terphenyl, tetraphenyl, etc., but is not limited thereto. As the aforementioned polycyclic aryl group, it can be naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, triphenylene, phenylene, fluorene, triphenylene, etc., but is not limited thereto.

[0059] In this specification, the aforementioned aryl group can be a monocyclic aryl group or a polycyclic aryl group (aryl group with two or more rings). A monocyclic aryl group can refer to a phenyl group or a group linked by two or more phenyl groups. Examples of monocyclic aryl groups include phenyl, biphenyl, terphenyl, tetraphenyl, etc., but are not limited to these. A polycyclic aryl group can refer to a group such as naphthyl, phenanthryl, etc., fused with two or more monocyclic rings. Examples of polycyclic aryl groups include naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, triphenyl, phenylene, fluorene, triphenylene, etc., but are not limited to these.

[0060] In this specification, the fluorene group can be substituted, and two substituents can combine with each other to form a spiro structure. In this case, the spiro structure can be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

[0061] When the aforementioned fluorene group is replaced, it can be used for , , Isospirofluorene; (9,9-dimethylfluorenyl) and Substituted fluorenyl groups such as (9,9-diphenylfluorenyl). However, it is not limited to these.

[0062] In this specification, the aryl group in the aryl group can be described in the above description of the aryl group.

[0063] In this specification, the alkyl groups in the above-mentioned alkylthio and alkylsulfonyl groups are subject to the above description of alkyl groups.

[0064] In this specification, the aryl groups in the above-mentioned aryl thiol and aryl sulfonyl groups are subject to the above description of aryl groups.

[0065] In this specification, a heterocyclic group is a cyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to another embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of heterocyclic groups include pyridyl, pyrroloyl, pyrimidinyl, quinolinyl, pyridazinyl, furanyl, thiopheneyl, imidazoyl, pyrazolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, benzocarbazoleyl, naphthobenzofuranyl, benzonaphthothiopheneyl, indenzocarbazoleyl, triazinyl, etc., but are not limited to these.

[0066] In this specification, heteroaryl refers to aromatic compounds; otherwise, the above description of heterocyclic groups applies.

[0067] In this specification, the above description of aryl groups applies, except that the aryl group is divalent.

[0068] In this specification, the above description of heterocyclic groups applies to divalent heterocyclic groups, except that they are divalent.

[0069] In this specification, "ring" refers to a hydrocarbon ring or heterocycle in the context of a substituted or unsubstituted ring formed by the combination of adjacent groups with each other.

[0070] The aforementioned hydrocarbon ring can be aromatic, aliphatic, or a fused ring of aromatic and aliphatic compounds, and can be selected from the examples of the aforementioned cycloalkyl or aryl groups.

[0071] In this specification, the term "forming a ring by bonding with adjacent groups" means forming a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic heterocycle, or a fused ring thereof by bonding with adjacent groups. The aforementioned hydrocarbon ring refers to a ring composed only of carbon and hydrogen atoms. The aforementioned heterocycle refers to a ring containing one or more elements selected from N, O, P, S, Si, and Se. In this specification, the aforementioned aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle, and aromatic heterocycle can be monocyclic or polycyclic.

[0072] In this specification, aliphatic hydrocarbon rings refer to non-aromatic rings composed only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene, but are not limited to these.

[0073] In this specification, aromatic hydrocarbon rings refer to aromatic rings composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenatene, pyrene, tetraphenylene, phenazine, pentaphenylene, fluorene, indene, acenaphthene, benzo[a]fluorene, spirofluorene, etc., but are not limited to these. In this specification, aromatic hydrocarbon rings can be interpreted in the same way as aryl groups.

[0074] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, and 1,4-dioxane. Alkane (1,4-dioxane), pyrrolidine, piperidine, morpholine, oxacycloheptane, azirrocyclooctane, thiocyclooctane, etc., but not limited to these.

[0075] In this specification, an aromatic heterocycle refers to an aromatic ring containing one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, etc. azole, isotonic azole, thiazole, isothiazole, triazole Diazole, thiadiazole, dithiazole, tetraazole, pyran, thiaran, diazine Azine, thiazide, diazine Alkenes, triazines, tetraazines, isoquinoline, quinoline, quinones, quinazoline, quinoxaline, naphthidine, acridine, phenanthridine, diazanaphthalene, triazaindene, indole, indolezine, benzothiazole, benzo[] azole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenazine It includes aziridines, indobenzocarbazole, indobenzocarbazole, etc., but is not limited to these.

[0076] The preferred embodiments of the present invention will now be described in detail. However, the embodiments of the present invention can be modified in various ways, and the scope of the present invention is not limited to the embodiments described below.

[0077] The chemical formula 1 of this invention is characterized by having a specific structured ortho-biphenyl linking group between the carbazole group and the amino group, wherein the phenylene group directly bonded to the amino group in the biphenylene contains an additional substituent R2.

[0078] When the compound represented by Chemical Formula 1 of this invention is applied to organic light-emitting devices, organic light-emitting devices with high efficiency, low voltage and / or long lifetime characteristics can be obtained.

[0079] The following is a detailed explanation of chemical formula 1.

[0080] [Chemical Formula 1]

[0081]

[0082] In the above chemical formula 1,

[0083] L1 and L2 may be the same or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group.

[0084] Ar1 and Ar2 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0085] R1 is hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring formed by combining with adjacent groups.

[0086] R2 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0087] a is an integer from 0 to 8. When a is 2 or more, two or more R1s are the same or different from each other.

[0088] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group.

[0089] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group with 6 to 60 carbon atoms.

[0090] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group with 6 to 30 carbon atoms.

[0091] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a directly bonded or arylene group having 6 to 30 carbon atoms.

[0092] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each independently is a directly bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthylene, substituted or unsubstituted phenanthylene, or substituted or unsubstituted fluorene.

[0093] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each independently is a directly bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, or substituted or unsubstituted naphthylene.

[0094] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a direct bond, phenylene, biphenylene, terphenylene, or naphthylene.

[0095] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each is independently a direct bond, a phenylene, or a biphenylene.

[0096] In one embodiment of this specification, L1 and L2 may be the same as or different from each other, and each may be independently represented by any of the following structural formulas.

[0097]

[0098] In the above structural formula, the dashed line indicates the connection position.

[0099] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0100] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each is independently an aryl group with 6 to 60 substituted or unsubstituted carbon atoms, or a heterocyclic group with 2 to 60 substituted or unsubstituted carbon atoms.

[0101] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each is independently an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heterocyclic group with 2 to 30 substituted or unsubstituted carbon atoms.

[0102] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each is independently an aryl group substituted or unsubstituted with an alkyl or aryl group, or a heterocyclic group substituted or unsubstituted with an alkyl or aryl group.

[0103] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each is independently an aryl group with 6 to 30 carbon atoms substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms, or a heterocyclic group containing O or S with 6 to 30 carbon atoms.

[0104] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each independently may be a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted tetraphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophene.

[0105] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each independently represents a phenyl group substituted or unsubstituted with an alkyl or aryl group, a biphenyl group substituted or unsubstituted with an alkyl or aryl group, a terphenyl group substituted or unsubstituted with an alkyl or aryl group, a tetraphenyl group substituted or unsubstituted with an alkyl or aryl group, a naphthyl group substituted or unsubstituted with an alkyl or aryl group, a phenanthryl group substituted or unsubstituted with an alkyl or aryl group, a fluorenyl group substituted or unsubstituted with an alkyl or aryl group, a triphenylene group substituted or unsubstituted with an alkyl or aryl group, a dibenzofuranyl group substituted or unsubstituted with an alkyl or aryl group, or a dibenzothiophenyl group substituted or unsubstituted with an alkyl or aryl group.

[0106] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each independently is a phenyl substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms, a biphenyl substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms, a terphenyl substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms, a tetraphenyl substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms, a naphthyl substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms, a phenanthyl substituted or unsubstituted with an aryl group having 6 to 30 carbon atoms, a fluorenyl substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms, a triphenylene, a dibenzofuranyl, or a dibenzothiophene.

[0107] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each independently is a phenyl group substituted or unsubstituted with naphthyl or phenanthrene, a biphenyl group substituted or unsubstituted with naphthyl, a terphenyl group, a tetraphenyl group, a naphthyl group substituted or unsubstituted with phenyl or biphenyl, a phenanthrene group, a fluorene group substituted or unsubstituted with methyl or phenyl, a triphenylene group, a dibenzofuranyl group, or a dibenzothiophenyl group.

[0108] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each independently is a phenyl substituted or unsubstituted with naphthyl or phenanthrene, a biphenyl substituted or unsubstituted with naphthyl, a terphenyl, a tetraphenyl, a naphthyl substituted or unsubstituted with phenyl or biphenyl, a phenanthrene, a dimethylfluorenyl, a diphenylfluorenyl, a triphenylene, a dibenzofuranyl, or a dibenzothiophene.

[0109] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each independently is a phenyl substituted or unsubstituted with naphthyl or phenanthrene, a biphenyl substituted or unsubstituted with naphthyl, a terphenyl, naphthyl, phenanthrene, dimethylfluorenyl, diphenylfluorenyl, triphenylene, or dibenzofuranyl.

[0110] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each may be independently represented by any of the following structural formulas.

[0111]

[0112]

[0113] In the above structural formula, the dashed line indicates the bonding position, and R6 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

[0114] In one embodiment of this specification, R6 is an alkyl group having 1 to 30 carbon atoms, either substituted or unsubstituted, or an aryl group having 6 to 60 carbon atoms, either substituted or unsubstituted.

[0115] In one embodiment of this specification, R6 is an alkyl group having 1 to 20 carbon atoms, either substituted or unsubstituted, or an aryl group having 6 to 30 carbon atoms, either substituted or unsubstituted.

[0116] In one embodiment of this specification, R6 is a substituted or unsubstituted methyl group or a substituted or unsubstituted phenyl group.

[0117] In one embodiment of this specification, R6 is methyl or phenyl.

[0118] In one embodiment of this specification, R1 is hydrogen, deuterium, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted ring formed by combining with adjacent groups.

[0119] In one embodiment of this specification, R1 is hydrogen, deuterium, an alkyl group with 1 to 30 substituted or unsubstituted carbon atoms, an aryl group with 6 to 60 substituted or unsubstituted carbon atoms, or a heterocyclic group with 2 to 60 substituted or unsubstituted carbon atoms, or a ring with 2 to 60 substituted or unsubstituted carbon atoms formed by combining with adjacent groups.

[0120] In one embodiment of this specification, R1 is hydrogen, deuterium, an alkyl group with 1 to 20 substituted or unsubstituted carbon atoms, an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heterocyclic group with 2 to 30 substituted or unsubstituted carbon atoms, or a ring with 2 to 30 substituted or unsubstituted carbon atoms formed by combining with adjacent groups.

[0121] In one embodiment of this specification, R1 is hydrogen, deuterium, 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 an aromatic hydrocarbon ring having 6 to 30 carbon atoms formed by combining with adjacent groups.

[0122] In one embodiment of this specification, R1 is hydrogen or deuterium, or it may combine with adjacent groups to form an aromatic hydrocarbon ring with 6 to 30 carbon atoms.

[0123] In one embodiment of this specification, R1 is hydrogen or deuterium, or it may combine with adjacent groups to form a benzene ring.

[0124] In one embodiment of this specification, R1 is hydrogen or deuterium.

[0125] In one embodiment of this specification, R1 is hydrogen.

[0126] In one embodiment of this specification, R2 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0127] In one embodiment of this specification, R2 is an aryl group with 6 to 60 substituted or unsubstituted carbon atoms, or a heterocyclic group with 2 to 60 substituted or unsubstituted carbon atoms.

[0128] In one embodiment of this specification, R2 is an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heterocyclic group with 2 to 30 substituted or unsubstituted carbon atoms.

[0129] In one embodiment of this specification, R2 is an aryl group having 6 to 30 carbon atoms, or a heterocyclic group having 2 to 30 carbon atoms.

[0130] In one embodiment of this specification, R2 is an aryl group having 6 to 30 carbon atoms, or a heterocyclic group having 2 to 30 carbon atoms containing O or S.

[0131] In one embodiment of this specification, R2 is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl.

[0132] In one embodiment of this specification, R2 is a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiopheneyl.

[0133] In one embodiment of this specification, R2 is phenyl, biphenyl, naphthyl, phenanthryl, dibenzofuranyl, or dibenzothiophene.

[0134] In one embodiment of this specification, R2 is phenyl, biphenyl, naphthyl, phenanthryl or dibenzofuranyl.

[0135] In one embodiment of this specification, R2 is represented by any of the following structural formulas.

[0136]

[0137] In the above structural formula, the dashed line indicates the connection position.

[0138] In one embodiment of this specification, R2 is represented by any of the following structural formulas.

[0139]

[0140] In the above structural formula, the dashed line indicates the connection position.

[0141] In one embodiment of this specification, a is an integer from 0 to 8.

[0142] In one embodiment of this specification, a is 0.

[0143] In one embodiment of this specification, a is 1.

[0144] In one embodiment of this specification, a is 8.

[0145] In one embodiment of this specification, the above chemical formula 1 is represented by the following chemical formula 1-1 or 1-2.

[0146] [Chemical Formula 1-1]

[0147]

[0148] [Chemical Formula 1-2]

[0149]

[0150] In the above chemical formulas 1-1 and 1-2, the definitions of L1, L2, Ar1, Ar2, R1, and a are the same as those in chemical formula 1.

[0151] R21 and R22 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0152] In one embodiment of this specification, R21 and R22 are defined the same as R2 as described above.

[0153] In one embodiment of this specification, the above chemical formula 1 is represented by any one of the following chemical formulas 2-1 to 2-5.

[0154] [Chemical Formula 2-1]

[0155]

[0156] [Chemical Formula 2-2]

[0157]

[0158] [Chemical Formula 2-3]

[0159]

[0160] [Chemical Formula 2-4]

[0161]

[0162] [Chemical Formula 2-5]

[0163]

[0164] In the above chemical formulas 2-1 to 2-5, the definitions of L1, L2, Ar1, Ar2, R1, and a are the same as those in chemical formula 1.

[0165] X is either O or S.

[0166] In one embodiment of this specification, X is 0.

[0167] In one embodiment of this specification, X is S.

[0168] In one embodiment of this specification, the above chemical formula 1 is represented by any one of the following chemical formulas 3-1 to 3-20.

[0169] [Chemical Formula 3-1] [Chemical Formula 3-2]

[0170]

[0171] [Chemical Formula 3-3] [Chemical Formula 3-4]

[0172]

[0173] [Chemical Formula 3-5] [Chemical Formula 3-6]

[0174]

[0175] [Chemical Formula 3-7] [Chemical Formula 3-8]

[0176]

[0177] [Chemical Formula 3-9] [Chemical Formula 3-10]

[0178]

[0179] [Chemical Formula 3-11] [Chemical Formula 3-12]

[0180]

[0181] [Chemical Formula 3-13] [Chemical Formula 3-14]

[0182]

[0183] [Chemical Formula 3-15] [Chemical Formula 3-16]

[0184]

[0185] [Chemical Formula 3-17] [Chemical Formula 3-18]

[0186]

[0187] [Chemical Formula 3-19] [Chemical Formula 3-20]

[0188]

[0189] In the above chemical formulas 3-1 to 3-20, the definitions of L1, L2, Ar1, Ar2, R1, and a are the same as those in chemical formula 1.

[0190] X is either O or S.

[0191] In one embodiment of this specification, the above chemical formula 1 is represented by any one of the following compounds.

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223] According to one embodiment of this specification, the compound represented by chemical formula 1 can be fabricated with a core structure as shown in reaction formula 1 below. Substituents can be combined by methods known in the art, and the type, position, or number of substituents can be varied according to techniques known in the art.

[0224] <Reaction Formula 1>

[0225]

[0226] In the above reaction formula 1, the definition of substituent is the same as that in the above chemical formula 1.

[0227] The process of synthesizing a compound with a specific substituent at a specific position is illustrated in the above reaction formula 1. However, compounds belonging to the scope of the above chemical formula 1 can be synthesized using starting materials, intermediate materials, etc., known in the art and synthetic methods known in the art.

[0228] In this specification, compounds with various band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by the above chemical formula 1. Furthermore, in this specification, the HOMO and LUMO energy levels of the compound can be tuned by introducing various substituents into the core structure of the structure shown above.

[0229] In addition, this specification provides organic light-emitting devices containing the compounds mentioned above.

[0230] In this specification, when it is stated that a component is "on" another component, it includes not only the case where one component is connected to another component, but also the case where there are other components between the two components.

[0231] In this specification, when a part is indicated to "include / contain" a certain component, unless otherwise stated, it means that other components may be included, rather than excluded.

[0232] The organic light-emitting device according to this specification is characterized in that it comprises: an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers contain a compound represented by the above chemical formula 1.

[0233] The organic light-emitting device described in this specification utilizes the compound of the above-mentioned chemical formula 1 to form an organic layer. Otherwise, it can be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0234] The aforementioned compounds can be used to form organic layers not only through vacuum evaporation but also through solution coating in the fabrication of organic light-emitting devices. Here, solution coating refers to methods such as spin coating, dip coating, inkjet printing, screen printing, spray coating, and roll coating, but is not limited to these.

[0235] The organic layers of the organic light-emitting device described in this specification can be formed as a single layer or as a multilayer structure with two or more organic layers stacked on top of each other. For example, the organic light-emitting device of this invention can have a structure comprising one or more of the following as organic layers: a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer. However, the structure of the organic light-emitting device described in this specification is not limited thereto, and may include fewer or more organic layers.

[0236] In the organic light-emitting device of this specification, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, hole transport layer, or hole injection and transport layer may contain a compound represented by the above chemical formula 1.

[0237] In the organic light-emitting device of this specification, the organic layer includes a hole transport layer or a hole injection layer, which may contain a compound represented by the above chemical formula 1.

[0238] In one embodiment of this specification, the organic layer includes an electron blocking layer comprising a compound represented by the above-described chemical formula 1.

[0239] In one embodiment of this specification, the organic layer includes an electron injection layer, an electron transport layer, an electron transport and injection layer, or a hole blocking layer, which may contain a compound represented by the above chemical formula 1.

[0240] In the organic light-emitting device described in this specification, the organic layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer, and the electron transport layer, electron injection layer, or electron transport and injection layer may contain a compound represented by the above chemical formula 1.

[0241] In one embodiment of this specification, the organic layer includes an electronic conditioning layer, which may contain a compound represented by the above-described chemical formula 1.

[0242] In one embodiment of this specification, the organic layer includes a hole-blocking layer comprising a compound represented by the above-described chemical formula 1.

[0243] In the organic light-emitting device of this specification, the organic layer is an electron transport and injection layer, and the electron transport and injection layer contains a compound represented by the above chemical formula 1.

[0244] In one embodiment of this specification, the thickness of the organic layer containing the compound of Formula 1 can be from 5 Å to 2000 Å or from 5 Å to 500 Å, preferably from 10 Å to 200 Å.

[0245] In one embodiment of this specification, the organic layer includes a light-emitting layer comprising a compound represented by the above-described chemical formula 1.

[0246] In one embodiment of this specification, the organic layer includes a light-emitting layer, which contains a compound represented by the above-described chemical formula 1 as the main component.

[0247] In one embodiment of this specification, the organic layer includes a light-emitting layer, which contains a compound represented by the above chemical formula 1 as a dopant.

[0248] In another embodiment, the organic layer may contain other organic compounds, metals, or metal compounds in addition to the compounds represented by the above chemical formula 1.

[0249] In an organic light-emitting device according to one embodiment of this specification, the light-emitting layer further comprises a fluorescent dopant or a phosphorescent dopant. In this case, the dopant in the light-emitting layer comprises 1 to 50 parts by weight relative to 100 parts by weight of the main body.

[0250] As another example, the aforementioned organic layer includes a light-emitting layer, which contains a compound represented by the aforementioned chemical formula 1 as the main body, and may also contain other main bodies.

[0251] In one embodiment of this specification, the dopant includes arylamine compounds, boron- and nitrogen-containing heterocyclic compounds, or Ir complexes, etc.

[0252] The organic light-emitting device described in this specification may also include one or more organic layers selected from the following: hole transport layer, hole injection layer, electron blocking layer, electron transport and injection layer, electron transport layer, electron injection layer, hole blocking layer, and hole injection and transport layer.

[0253] In one embodiment of this specification, the organic light-emitting device includes an anode, a cathode, and two or more organic layers disposed between the anode and the cathode, wherein at least one of the two or more organic layers contains a compound represented by the above chemical formula 1.

[0254] In one embodiment of this specification, the two or more organic layers mentioned above can be selected from the group consisting of a light-emitting layer, a hole transport layer, a hole injection layer, a hole transport and injection layer, and an electron blocking layer.

[0255] In one embodiment of this specification, the two or more organic layers mentioned above can be selected from the group consisting of a light-emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron modulation layer, and a hole blocking layer.

[0256] In one embodiment of this specification, the aforementioned organic layer comprises two or more electron transport layers, and at least one of the two or more electron transport layers contains a compound represented by the aforementioned chemical formula 1. Specifically, in one embodiment of this specification, the compound represented by the aforementioned chemical formula 1 may be contained in one of the two or more electron transport layers, or it may be contained in each of the two or more electron transport layers.

[0257] In addition, in one embodiment of this specification, when the above-mentioned compound is contained in each of the two or more electron transport layers, the other materials besides the compound represented by the above-mentioned chemical formula 1 may be the same as or different from each other.

[0258] When the organic layer containing the compound represented by the above chemical formula 1 is an electron transport layer, an electron injection layer, or an electron transport and injection layer, the electron transport layer, electron injection layer, or electron transport and injection layer may further contain an n-type dopant or an organometallic compound. The aforementioned n-type dopant or organometallic compound may be made of materials known in the art, for example, a metal or a metal complex.

[0259] For example, the aforementioned n-type dopant or organometallic compound can be LiQ, but is not limited thereto. The electron transport layer, electron injection layer, or electron transport and injection layer comprising a compound represented by the aforementioned chemical formula 1 may also comprise LiQ (Lithium Quinolate).

[0260] According to one example, the compound represented by the above chemical formula 1 and the above-described n-type dopant or organometallic compound may be contained in a weight ratio of 2:8 to 8:2, such as 4:6 to 6:4. According to another example, the compound represented by the above chemical formula 1 and the above-described n-type dopant or organometallic compound may be contained in a weight ratio of 1:1.

[0261] In one embodiment of this specification, the aforementioned organic layer comprises two or more hole transport layers, and at least one of the two or more hole transport layers contains a compound represented by the aforementioned chemical formula 1. Specifically, in one embodiment of this specification, the compound represented by the aforementioned chemical formula 1 may be contained in one of the two or more hole transport layers, or it may be contained in each of the two or more hole transport layers.

[0262] Furthermore, in one embodiment of this specification, when the compound represented by the above chemical formula 1 is included in each of the two or more hole transport layers, the other materials besides the compound represented by the above chemical formula 1 may be the same as or different from each other.

[0263] In one embodiment of this specification, the organic layer may include, in addition to an organic layer containing a compound represented by the above-described chemical formula 1, a hole injection layer or a hole transport layer, which contains a compound containing an arylamine group, a carbazole group, or a benzocarbazole group.

[0264] In one embodiment of this specification, the organic light-emitting device may be an organic light-emitting device with an anode, one or more organic layers and a cathode sequentially stacked on a substrate (normal type).

[0265] In one embodiment of this specification, the organic light-emitting device may be an organic light-emitting device with a reverse structure (inverted type) in which a cathode, one or more organic layers and an anode are sequentially stacked on a substrate.

[0266] In the organic light-emitting device of the present invention, the organic layer may include an electron blocking layer, which may use materials known in the art.

[0267] For example, the organic light-emitting device described above can have a stacked structure as shown below, but is not limited to this.

[0268] (1) Anode / hole transport layer / light-emitting layer / cathode

[0269] (2) Anode / hole injection layer / hole transport layer / light emission layer / cathode

[0270] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0271] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0272] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0273] (6) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / cathode

[0274] (7) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode

[0275] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light emission layer / electron transport layer / cathode

[0276] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode

[0277] (10) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Cathode

[0278] (11) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Electron injection layer / Cathode

[0279] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light emission layer / electron transport layer / cathode

[0280] (13) Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode

[0281] (14) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0282] (15) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0283] (16) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0284] (17) Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0285] (18) Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emitting layer / Hole blocking layer / Electron transport and injection layer / Cathode

[0286] The organic light-emitting device structure described in this specification can have the following characteristics: Figures 1 to 3 The structure shown is not limited to this.

[0287] Figure 1 The illustration 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 the structure described above, the aforementioned compound may be included in the light-emitting layer 6.

[0288] Figure 2 The illustration shows an example of an organic light-emitting device comprising, in sequence, 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, an electron transport layer 8, an electron injection layer 9, and a cathode 10. In the structure described above, the aforementioned compound may be contained within the hole injection layer 3, hole transport layer 4, electron blocking layer 5, light-emitting layer 6, hole blocking layer 7, electron transport layer 8, or electron injection layer 9.

[0289] Figure 3 The illustration shows an example of an organic light-emitting device comprising, in sequence, 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, an electron transport and injection layer 11, and a cathode 10. In the structure described above, the aforementioned compound may be contained in 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.

[0290] In one embodiment of this specification, the electron blocking layer and the light-emitting layer may be disposed adjacent to each other. For example, the electron blocking layer and the light-emitting layer may be physically connected.

[0291] In one embodiment of this specification, the hole transport layer and the electron blocking layer may be disposed adjacent to each other. For example, the hole transport layer and the electron blocking layer may be physically connected.

[0292] The organic light-emitting device described in this specification, except that one or more layers of the organic material contain the aforementioned compound, i.e., the compound represented by the aforementioned chemical formula 1, can be manufactured using materials and methods known in the art.

[0293] When the aforementioned organic light-emitting device comprises a plurality of organic layers, the organic layers may be formed from the same substance or different substances.

[0294] For example, the organic light-emitting device according to this specification can be manufactured as follows: An anode is formed by depositing a metal or a conductive metal oxide or alloy thereof onto a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation. Then, an organic layer comprising 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 is formed on the anode. Finally, a material suitable for use as a cathode is deposited onto the organic layer. Alternatively, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto a substrate.

[0295] The aforementioned organic layer may further include one or more of the following: 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. In one embodiment of this specification, the organic layer may include one or more of the following: 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.

[0296] The aforementioned organic layer can be 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 electron transport, electron injection, and electron transport and injection layers, but it is not limited to this; it can also be a single-layer structure. Furthermore, the aforementioned organic layer can be manufactured in smaller quantities using various polymer materials and solvent processes other than vapor deposition, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer.

[0297] The anode described above is the electrode for injecting holes. As the anode material, it is generally preferred to be a material with a high work function in order to enable holes to be smoothly injected into the organic layer. Specific examples of anode materials that can be used in this invention include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; 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 SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylidene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0298] The cathode described above is the electrode into which electrons are injected. As a cathode material, it is generally preferred to be a material with a low work function in order to facilitate the injection of electrons into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer structures such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0299] The aforementioned hole injection layer facilitates the injection of holes from the anode to the light-emitting layer. The hole injection material is one that can effectively receive holes from the anode at low voltages. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organic compounds, hexanitrile hexaazabenzophenanthrene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinones, and conductive polymers based on polyaniline and polythiophene. The thickness of the hole injection layer can range from 1 nm to 150 nm. When the thickness of the hole injection layer is 1 nm or more, it has the advantage of preventing a decrease in hole injection characteristics; when it is less than 150 nm, it has the advantage of preventing an increase in driving voltage to improve hole migration when the hole injection layer is too thick.

[0300] In one embodiment of this specification, the hole injection layer may comprise an arylamine compound containing a carbazole group and a p-type dopant. As an example, the amine compound is represented as Het101-L101-N(Ar101)(Ar102), where Het101 is a substituted or unsubstituted carbazole group, L101 is a directly bonded, or substituted or unsubstituted aryl group, and Ar101 and Ar102 may be the same as or different from each other, each independently being a substituted or unsubstituted aryl group. The amine compound and p-type dopant may be contained in a suitable molar ratio; as an example, the amine compound and p-type dopant may be contained in a molar ratio of 99.9:0.1 to 90:10.

[0301] The aforementioned hole transport layer facilitates hole transport. The hole transport material is capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer; materials with high hole mobility are suitable. Specific examples include aryl amine-based organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but these are not limited to these.

[0302] In one embodiment of this specification, the hole transport layer may contain an arylamine compound containing a carbazole group.

[0303] A hole buffer layer may be further provided between the hole injection layer and the hole transport layer, which may contain materials known in the art for hole injection or transport.

[0304] An electron blocking layer may be disposed between the hole transport layer and the light-emitting layer. The aforementioned compounds or materials known in this art can be used in the electron blocking layer.

[0305] In one embodiment of this specification, the electron blocking layer may comprise a compound represented by chemical formula 1 of this invention.

[0306] The aforementioned luminescent layer can emit red, green, or blue light and can be formed from phosphorescent or fluorescent substances. The luminescent substance is capable of receiving holes and electrons from the hole transport layer and electron transport layer respectively, and combining them to emit light in the visible light region; preferably, it is a substance with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complexes (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Compounds including azoles, benzothiazoles and benzimidazoles; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene, fluorene, etc., but not limited to these.

[0307] The main materials for the luminescent layer include aromatic fused-ring derivatives or heterocyclic compounds. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, and fluoranthene compounds, while heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but are not limited to these.

[0308] When the emissive layer emits red light, phosphorescent dopants such as PIQIr(acac) (bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac) (bis(1-phenylquinoline)acetylacetonateiridium), PQIr (tris(1-phenylquinoline)iridium), PtOEP (octaethylporphyrin platinum), or fluorescent substances such as Alq3 (tris(8-hydroxyquinolino)aluminum) can be used, but are not limited to these. When the luminescent layer emits green light, phosphorescent materials such as Ir(ppy)3 (fac tris(2-phenylpyridine)iridium, or fluorescent materials such as Alq3 (tris(8-hydroxyquinoline)aluminum) can be used as luminescent dopants, but these are not the only options. When the luminescent layer emits blue light, phosphorescent materials such as (4,6-F2ppy)2Irpic, or fluorescent materials such as spiro-DPVBi, spiro-6P, stilbene (DSB), stilbene arylene (DSA), PFO-based polymers, and PPV-based polymers can be used as luminescent dopants, but these are not the only options.

[0309] In one embodiment of this specification, the light-emitting layer comprises an anthracene compound substituted with aryl or heterocyclic groups as a host, and may comprise a pyrene compound substituted with amine groups as a dopant. According to one example, the anthracene compound has a structure in which carbons 9 and 10 are substituted with aryl or heterocyclic groups. The host and dopant may be contained in a suitable weight ratio; according to one example, the host and dopant may be contained in a weight ratio of 100:1 to 100:10.

[0310] A hole blocking layer can be provided between the electron transport layer and the light-emitting layer, and materials known in this art can be used.

[0311] In one embodiment of this specification, the hole-blocking layer may comprise a compound having an N-containing heterocyclic group and a fluorene ring.

[0312] The aforementioned electron transport layer facilitates electron transport. The electron transport material is one that can effectively receive electrons from the cathode and transfer them to the light-emitting layer; materials with high electron mobility are suitable. Specific examples include the compounds mentioned above, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, and hydroxyflavonoid-metal complexes, but these are not limited to these. The thickness of the electron transport layer can range from 1 nm to 50 nm. When the thickness of the electron transport layer is greater than 1 nm, it has the advantage of preventing a decrease in electron transport properties; when it is less than 50 nm, it has the advantage of preventing an increase in driving voltage to improve electron migration when the electron transport layer is too thick.

[0313] In one embodiment of this specification, the electron transport layer may comprise a compound containing two N-containing heterocyclic groups, and may also comprise an n-type dopant or an organometallic compound. According to one example, the n-type dopant or organometallic compound may be LiQ, and may comprise the compound containing two N-containing heterocyclic groups and the n-type dopant (or organometallic compound) in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.

[0314] The aforementioned electron injection layer facilitates electron injection. Preferred electron injection materials include compounds that possess electron transport capabilities, effectively inject electrons from the cathode, exhibit excellent electron injection performance for the luminescent layer or luminescent material, prevent excitons generated in the luminescent layer from migrating to the hole injection layer, and demonstrate excellent thin-film formation ability. Specifically, these include fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, but not limited to these.

[0315] Examples of the aforementioned metal coordination compounds include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)gallium chloride, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, and bis(2-methyl-8-quinoline)(2-naphthol)gallium, but are not limited to these.

[0316] The aforementioned hole-blocking layer is a layer that prevents holes from reaching the cathode, and it can typically be formed using the same conditions as the hole injection layer. Specifically, there are... Diazole or triazole derivatives, phenanthrene-rhein derivatives, BCP, aluminum complexes, etc., but not limited to these.

[0317] Depending on the materials used, the organic light-emitting device according to the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0318] The organic light-emitting devices according to this specification can be included in and used in various electronic devices. For example, the aforementioned electronic devices can be display panels, touch panels, solar modules, lighting devices, etc., but are not limited thereto.

[0319] Methods of implementing the invention

[0320] The following detailed description, using embodiments, aims to provide a more specific explanation of this specification. However, the embodiments described herein can be modified in various ways and are not intended to limit the scope of this application to the embodiments detailed below. These embodiments are provided to provide a more complete explanation of this specification to those skilled in the art.

[0321] Manufacturing Example 1: Manufacturing of Compound 1

[0322]

[0323] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-(4'-chloro-[1,1':3',1''-terphenyl]-2-yl)-9H-carbazole (4.50 g, 10.47 mmol) and compound a1 (4.37 g, 10.99 mmol) were completely dissolved in 240 mL of xylene. Then, NaOtBu (1.31 g, 13.60 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.16 g, 0.31 mmol) were added, and the mixture was heated and stirred for 5 hours. The temperature was lowered to room temperature, the base was removed by filtration, the xylene was concentrated under reduced pressure, and recrystallized with 230 mL of ethyl acetate to produce compound 1 (5.78 g, yield: 70%).

[0324] MS[M+H] + =792

[0325] Manufacturing Example 2: Manufacturing of Compound 2

[0326]

[0327] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-(4'-chloro-1,1':3',1''-terphenyl]-2-yl)-9H-carbazole (4.50 g, 10.47 mmol) and compound a2 (4.07 g, 10.99 mmol) were completely dissolved in 240 mL of xylene. NaOtBu (1.31 g, 13.60 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.16 g, 0.31 mmol) were added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to produce compound 2 (4.86 g, yield: 61%).

[0328] MS[M+H] + =765

[0329] Manufacturing Example 3: Manufacturing of Compound 3

[0330]

[0331] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-(4'-chloro-1,1':3',1''-terphenyl]-2-yl)-9H-carbazole (4.50 g, 10.47 mmol) and compound a3 (3.96 g, 10.99 mmol) were completely dissolved in 250 mL of xylene. NaOtBu (1.31 g, 13.60 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.16 g, 0.31 mmol) were added, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized from 230 mL of ethyl acetate to produce compound 3 (5.27 g, yield: 67%).

[0332] MS[M+H] + =755

[0333] Manufacturing Example 4: Manufacturing of Compound 4

[0334]

[0335] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-(4'-chloro-1,1':3',1''-terphenyl]-2-yl)-9H-carbazole (4.50 g, 10.47 mmol) and compound a4 (3.78 g, 10.99 mmol) were completely dissolved in 250 mL of xylene. NaOtBu (1.31 g, 13.60 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.16 g, 0.31 mmol) were added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized from 240 mL of ethyl acetate to prepare compound 4 (4.95 g, yield: 64%).

[0336] MS[M+H] + =739

[0337] Manufacturing Example 5: Manufacturing of Compound 5

[0338]

[0339] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-(4'-chloro-1,1':3',1''-terphenyl]-2-yl)-9H-carbazole (4.50 g, 10.47 mmol) and compound a5 (4.09 g, 10.99 mmol) were completely dissolved in 250 mL of xylene. NaOtBu (1.31 g, 13.60 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.16 g, 0.31 mmol) were added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized from 240 mL of ethyl acetate to produce compound 5 (5.63 g, yield: 70%).

[0340] MS[M+H] + =767

[0341] Manufacturing Example 6: Manufacturing of Compound 6

[0342]

[0343] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-(4'-chloro-1,1':3',1''-terphenyl]-2-yl)-9H-carbazole (4.50 g, 10.47 mmol) and compound a6 (3.67 g, 10.99 mmol) were completely dissolved in 250 mL of xylene. NaOtBu (1.31 g, 13.60 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.16 g, 0.31 mmol) were added, followed by heating and stirring for 5 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to produce compound 6 (4.11 g, yield: 54%).

[0344] MS[M+H] + =729

[0345] Manufacturing Example 7: Manufacturing of Compound 7

[0346]

[0347] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-(4'-chloro-[1,1':2',1''-terphenyl]-2-yl)-9H-carbazole (4.50 g, 10.47 mmol) and compound a7 (4.66 g, 10.99 mmol) were completely dissolved in 250 mL of xylene. NaOtBu (1.31 g, 13.60 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.16 g, 0.31 mmol) were added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, and after filtration to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized from 230 mL of ethyl acetate to produce compound 7 (5.78 g, yield: 68%).

[0348] MS[M+H] + =816

[0349] Manufacturing Example 8: Manufacturing of Compound 8

[0350]

[0351] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-(4'-chloro-[1,1':2',1''-terphenyl]-2-yl)-9H-carbazole (4.50 g, 10.47 mmol) and compound a8 (3.56 g, 10.99 mmol) were completely dissolved in 250 mL of xylene. NaOtBu (1.31 g, 13.60 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.16 g, 0.31 mmol) were added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized from 250 mL of ethyl acetate to produce compound 8 (4.81 g, yield: 64%).

[0352] MS[M+H] + =713

[0353] Manufacturing Example 9: Manufacturing of Compound 9

[0354]

[0355] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-(4'-chloro-[1,1':2',1''-terphenyl]-2-yl)-9H-carbazole (4.50 g, 10.47 mmol) and compound a9 (4.56 g, 10.99 mmol) were completely dissolved in 230 mL of xylene. NaOtBu (1.31 g, 13.60 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.16 g, 0.31 mmol) were added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized from 250 mL of tetrahydrofuran to produce compound 9 (5.14 g, yield: 61%).

[0356] MS[M+H] + =804

[0357] Manufacturing Example 10: Manufacturing of Compound 10

[0358]

[0359] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-(4'-chloro-[1,1':2',1''-terphenyl]-2-yl)-9H-carbazole (4.50 g, 10.47 mmol) and compound a10 (3.90 g, 10.99 mmol) were completely dissolved in 230 mL of xylene. NaOtBu (1.31 g, 13.60 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.16 g, 0.31 mmol) were added, followed by heating and stirring for 4 hours. The temperature was lowered to room temperature, and after filtering to remove the alkali, the xylene was concentrated under reduced pressure and recrystallized from 230 mL of ethyl acetate to produce compound 10 (5.52 g, yield: 71%).

[0360] MS[M+H] + =745

[0361] Manufacturing Example 11: Manufacturing of Compound 11

[0362]

[0363] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-(4'-chloro-2'-(naphthalen-1-yl)-[1,1'-biphenyl]-2-yl)-9H-carbazole (3.50 g, 7.29 mmol) and compound a11 (2.64 g, 7.66 mmol) were completely dissolved in 230 mL of xylene. NaOtBu (0.91 g, 9.48 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.11 g, 0.22 mmol) were added, and the mixture was heated and stirred for 3 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, and the xylene was concentrated under reduced pressure and recrystallized from 210 mL of ethyl acetate to produce compound 11 (3.94 g, yield: 68%).

[0364] MS[M+H] + =789

[0365] Manufacturing Example 12: Manufacturing of Compound 12

[0366]

[0367] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-(4'-chloro-[1,1':2',1'':4'',1'''-tetraphenyl]-2-yl)-9H-carbazole (3.50 g, 6.92 mmol) and compound a12 (2.14 g, 7.26 mmol) were completely dissolved in 210 mL of xylene. NaOtBu (0.86 g, 8.99 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.11 g, 0.21 mmol) were added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, the xylene was concentrated under reduced pressure, and recrystallized with 170 mL of ethyl acetate to produce compound 12 (4.11 g, yield: 61%).

[0368] MS[M+H] + =765

[0369] Manufacturing Example 13: Manufacturing of Compound 13

[0370]

[0371] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-(4'-chloro-2'-(phenanthren-9-yl)-[1,1'-biphenyl]-2-yl)-9H-carbazole (3.50 g, 6.60 mmol) and compound a13 (1.70 g, 6.93 mmol) were completely dissolved in 230 mL of xylene. Then, NaOtBu (0.83 g, 8.58 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.10 g, 0.20 mmol) were added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, the xylene was concentrated under reduced pressure, and recrystallized with 230 mL of tetrahydrofuran to produce compound 13 (2.56 g, yield: 52%).

[0372] MS[M+H] + =739

[0373] Manufacturing Example 14: Manufacturing of Compound 14

[0374]

[0375] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-(4'-chloro-2'-(naphthalen-2-yl)-[1,1'-biphenyl]-2-yl)-9H-carbazole (3.50 g, 7.29 mmol) and compound a14 (2.26 g, 7.66 mmol) were completely dissolved in 230 mL of xylene. NaOtBu (0.91 g, 9.48 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.11 g, 0.22 mmol) were added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, and the xylene was concentrated under reduced pressure and recrystallized from 230 mL of ethyl acetate to produce compound 14 (10.57 g, yield: 61%).

[0376] MS[M+H] + =739

[0377] Manufacturing Example 15: Manufacturing of Compound 15

[0378]

[0379] Under a nitrogen atmosphere, in a 500 mL round-bottom flask, compound 9-(4'-chloro-2'-(dibenzo[b,d]furan-3-yl)-[1,1'-biphenyl]-2-yl)-9H-carbazole (3.50 g, 6.73 mmol) and compound a15 (2.27 g, 7.07 mmol) were completely dissolved in 230 mL of xylene. Then, NaOtBu (0.84 g, 8.75 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.10 g, 0.20 mmol) were added, and the mixture was heated and stirred for 4 hours. The temperature was lowered to room temperature, the alkali was removed by filtration, the xylene was concentrated under reduced pressure, and recrystallized with 230 mL of ethyl acetate to produce compound 15 (3.12 g, yield: 58%).

[0380] MS[M+H] + =805

[0381] Example 1-1

[0382] A glass substrate coated with an ITO (indium tin oxide) film at a thickness of 1000 Å was immersed in distilled water containing a detergent and ultrasonically washed. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, the ultrasonic washing was repeated twice with distilled water for 10 minutes each time. Following the distilled water washing, the substrate was ultrasonically washed with a solvent of isopropanol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0383] On the prepared ITO transparent electrode serving as the anode, a hole injection layer is formed by thermal vacuum evaporation of compounds HI1 and HI2 in a molar ratio of 98:2 with a thickness of 100 Å. On the hole injection layer, a hole transport layer is formed by vacuum evaporation of a compound represented by the chemical formula HT1 (1150 Å). Next, on the hole transport layer, an electron blocking layer is formed by vacuum evaporation of compound 1 manufactured in Manufacturing Example 1 with a film thickness of 50 Å. Next, on the electron blocking layer, a light-emitting layer is formed by vacuum evaporation of compounds represented by the chemical formula BH and BD in a weight ratio of 25:1 with a film thickness of 200 Å. On the light-emitting layer, a hole blocking layer is formed by vacuum evaporation of a compound represented by the chemical formula HB1 with a film thickness of 50 Å. Next, on the hole-blocking layer, a compound represented by the chemical formula ET1 and a compound represented by the chemical formula LiQ are vacuum-deposited in a 1:1 weight ratio to form an electron injection and transport layer with a thickness of 310 Å. On the electron injection and transport layer, lithium fluoride (LiF) is sequentially deposited with a thickness of 12 Å and aluminum with a thickness of 1000 Å to form a cathode.

[0384]

[0385] During the above process, the evaporation rate of organic materials was maintained at 0.4 to 0.7 Å / sec, the evaporation rate of lithium fluoride at the cathode was maintained at 0.3 Å / sec, and the evaporation rate of aluminum was maintained at 2 Å / sec. During evaporation, the vacuum level was maintained at 2 × 10⁻⁶. -7 Up to 5×10 -6 This led to the creation of organic light-emitting devices.

[0386] Examples 1-2 to Examples 1-15

[0387] Organic light-emitting devices were manufactured by the same method as in Examples 1-1 above, except that the compounds listed in Table 1 below were used instead of Compound 1.

[0388]

[0389] Comparative Examples 1-1 to 1-5

[0390] Organic light-emitting devices were manufactured using the compounds listed in Table 1 below instead of compound 1, except that the method was the same as in Examples 1-1 above. The compounds EB1, EB2, EB3, EB4, and EB5 used in Table 1 below are shown below.

[0391]

[0392] An application of 10 mA / cm² to the organic light-emitting devices manufactured in the above embodiments and comparative examples 2 At the given current, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nits) to 95%.

[0393] [Table 1]

[0394]

[0395] As shown in Table 1 above, organic light-emitting devices using the compounds of the present invention as electron blocking layers exhibit excellent characteristics in terms of efficiency, driving voltage, and stability.

[0396] As shown in Examples 1-1 to 1-15, it can be seen that when a substance with an additional substituent (R2) attached to the phenylene oxide linked to the amine in the ortho-biphenylene oxide is used as an electron blocking layer, it exhibits characteristics of low voltage, high efficiency and long lifetime.

[0397] As shown in Comparative Examples 1-1 to 1-5, when compounds EB1 to EB5 containing linking groups such as meta-biphenyl or para-biphenyl having a structure different from that of the ortho-biphenyl of the present invention, or containing ortho-biphenyl with unsubstituted R2, are used, the voltage increases, the efficiency decreases, and in particular, the stability (lifetime) is reduced by more than 4 times.

[0398] The preferred embodiment (electron blocking layer) of the present invention has been described above, but the present invention is not limited thereto. Various modifications can be made within the scope of the claims and detailed description of the invention, and these modifications also fall within the scope of the present invention.

Claims

1. A compound represented by the following chemical formula 1: [Chemical Formula 1] In the chemical formula 1, L1 is a direct bond. Ar1 is a phenyl group that is either deuterated or unsubstituted. L2 can be a directly bonded, deuterated or unsubstituted phenylene, deuterated or unsubstituted biphenylene, deuterated or unsubstituted terphenylene, or deuterated or unsubstituted naphthylene. Ar2 is a phenyl group substituted or unsubstituted with deuterium, naphthyl, or phenanthrene; a biphenyl group substituted or unsubstituted with deuterium or naphthyl; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium, phenyl, or biphenyl; a phenanthrene group substituted or unsubstituted with deuterium; an unsubstituted dimethylfluorenyl group; an unsubstituted diphenylfluorenyl group; a triphenylene group substituted or unsubstituted with deuterium; a dibenzofuranyl group substituted or unsubstituted with deuterium; or a dibenzothiophenyl group substituted or unsubstituted with deuterium. R1 is hydrogen. R2 is a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, a deuterated or unsubstituted naphthyl, a deuterated or unsubstituted phenanthyl, a deuterated or unsubstituted fluorenyl, a deuterated or unsubstituted dibenzofuranyl, or a deuterated or unsubstituted dibenzothiopheneyl. a is 0.

2. The compound according to claim 1, wherein, The chemical formula 1 is represented by the following chemical formula 1-1 or 1-2: [Chemical Formula 1-1] [Chemical Formula 1-2] In chemical formulas 1-1 and 1-2, the definitions of L1, L2, Ar1, Ar2, R1, and a are the same as those in chemical formula 1. R21 and R22 may be the same as or different from each other, and each may independently be a deuterated or unsubstituted phenyl, a deuterated or unsubstituted biphenyl, a deuterated or unsubstituted naphthyl, a deuterated or unsubstituted phenanthyl, a deuterated or unsubstituted fluorenyl, a deuterated or unsubstituted dibenzofuranyl, or a deuterated or unsubstituted dibenzothiopheneyl.

3. The compound according to claim 1, wherein, The chemical formula 1 is represented by any one of the following chemical formulas 2-1 to 2-5: [Chemical Formula 2-1] [Chemical Formula 2-2] [Chemical Formula 2-3] [Chemical Formula 2-4] [Chemical Formula 2-5] In chemical formulas 2-1 to 2-5, the definitions of L1, L2, Ar1, Ar2, R1, and a are the same as those in chemical formula 1. X is either O or S.

4. The compound according to claim 1, wherein, Chemical Formula 1 is represented by any of the following compounds: 。 5. An organic light-emitting device, comprising: anode, cathode, and One or more organic layers are disposed between the anode and the cathode. Wherein, one or more of the organic layers comprise the compound according to any one of claims 1 to 4.

6. The organic light-emitting device according to claim 5, wherein, The organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, wherein the hole injection layer, hole transport layer, or hole injection and transport layer contains the compound.

7. The organic light-emitting device according to claim 5, wherein, The organic layer includes an electron blocking layer, which contains the compound.

8. The organic light-emitting device according to claim 5, wherein, The organic layer includes one or more of the following: 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.

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