Compound and organic light-emitting device comprising same

Abstract

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

Description

Technical Field

[0001] The present invention relates to a compound and an organic light-emitting device including the same.

[0002] This application claims the priority of Korean Patent Application No. 10-2023-0077625 filed with the Korean Patent Office on June 16, 2023 and Korean Patent Application No. 10-2024-0072512 filed with the Korean Patent Office on June 3, 2024, the entire contents of which are incorporated into this specification. Background Art

[0003] Generally speaking, the phenomenon of organic light emitting refers to the phenomenon of converting electrical energy into light energy using organic substances. An organic light emitting device using the phenomenon of organic light emitting generally has a structure including an anode and a cathode and an organic layer located between them. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is mostly formed by a multilayer structure composed of different substances, for example, it can be formed by a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. For the structure of such an organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when the excitons re-transition to the ground state, light is emitted.

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

[0005] Prior art literature

[0006] Patent Literature

[0007] China Patent Publication No. 107663214 Summary of the invention

[0008] Technical issues

[0009] The present specification provides a compound and an organic light-emitting device including the same.

[0010] Solution to the problem

[0011] One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.

[0012] [Chemical formula 1]

[0013]

[0014] In the above chemical formula 1,

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

[0016] L1 to L3 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

[0017] R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0018] R3 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted silyl group, an unsubstituted aryl group having 10 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylalkenyl group, or a substituted or unsubstituted heterocyclic group containing O or S,

[0019] a to e are integers of 1 to 4, and when a to e is 2 or more, two or more R1 to R5 are the same or different from each other,

[0020] p to r are integers of 1 to 4, and when p to r is 2 or more, two or more L1 to L3 are the same as or different from each other.

[0021] In addition, one embodiment of the present specification provides an organic light-emitting device, which includes: an anode, a cathode, and one or more organic layers arranged between the anode and the cathode, and one or more of the organic layers contain the compound represented by the above Chemical Formula 1.

[0022] Effects of the Invention

[0023] The compound described in this specification can be used as a material for an organic layer of an organic light-emitting device. The compound according to at least one embodiment of this specification can achieve improved efficiency, lower driving voltage, and / or improved lifespan characteristics in an organic light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0024] Figure 1 An example of an organic light-emitting device in which a substrate 1, an anode 2, a light-emitting layer 6, and a cathode 9 are stacked in this order is shown.

[0025] Figure 2 The diagram 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 injection and transport layer 8, and a cathode 9 are stacked in this order.

[0026] Explanation of symbols

[0027] 1: Substrate

[0028] 2: Anode

[0029] 3: Hole injection layer

[0030] 4: Hole transport layer

[0031] 5: Electron blocking layer

[0032] 6: Luminous layer

[0033] 7: Hole blocking layer

[0034] 8: Electron injection and transport layer

[0035] 9: Cathode DETAILED DESCRIPTION

[0036] Next, this specification is described in more detail.

[0037] In the present specification, when it is indicated that a certain part “includes / comprises” a certain constituent element, unless there is a particular description to the contrary, it means that other constituent elements may be further included, rather than excluding other constituent elements.

[0038] In the present specification, when it is mentioned that a certain component is located “on” another component, it not only includes the case where the certain component is in contact with the other component, but also includes the case where other components exist between the two components.

[0039] The term "substituted" mentioned above means that a hydrogen atom bonded to a carbon atom of a compound is replaced by another substituent. The substituted position is not limited as long as it is a position where a hydrogen atom can be substituted, that is, a position where a substituent can be substituted. When there are more than two substitutions, the two or more substituents may be the same or different from each other.

[0040] In the present specification, the term "substituted or unsubstituted" refers to a group selected from deuterium, a halogen group, a nitrile group (-CN), a nitro group, a hydroxyl group, an alkyl group, a cycloalkyl group, an alkoxy group, a phosphine oxide group, an aryloxy group, an alkylthio group, Arylthio Alkylsulfonyl Arylsulfonyl The alkylene group may be substituted with one or more substituents selected from the group consisting of alkenyl, silyl, boronyl, amine, aryl or heterocyclic groups, or may be substituted with a substituent formed by connecting two or more substituents selected from the group consisting of the above-mentioned substituents, or may not have any substituent. For example, the "substituent formed by connecting two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent formed by connecting two phenyl groups.

[0041] In the present specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, a halogen group, a nitrile group, a nitro group, a hydroxyl group, an amino group, a silyl group, a boron group, an alkoxy group, an aryloxy group, an alkyl group, a cycloalkyl group, an aryl group, and a heterocyclic group, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.

[0042] In this specification, the term "substituted or unsubstituted" means substituted with one or more substituents selected from deuterium, a halogen group, a nitrile group, an alkyl group, an aryl group, and a heterocyclic group, or substituted with a substituent formed by connecting two or more substituents among the substituents exemplified above, or having no substituent.

[0043] Examples of the above substituents are described below, but are not limited thereto.

[0044] In the present specification, as examples of the halogen group, there are fluorine (—F), chlorine (—Cl), bromine (—Br) or iodine (—I).

[0045] In this specification, the silyl group can be represented by -SiY a Y b Y c The chemical formula of Y a , Y b and Y c Each of them can be hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl. The above-mentioned silyl group specifically includes trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, etc., but is not limited thereto.

[0046] In this specification, the boron group can be represented by -BY d Y e The chemical formula of Y d and Y e Each of them may be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. Specific examples of the boryl group include trimethylboryl, triethylboryl, tert-butyldimethylboryl, triphenylboryl, phenylboryl, and the like, but are not limited thereto.

[0047] In the present specification, the alkyl group may be linear 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 embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of the alkyl group 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 thereto.

[0048] In the present specification, the above description about the alkyl group is applicable to the arylalkyl group except that the arylalkyl group is substituted with an aryl group.

[0049] In this specification, the alkoxy group may be straight chain, branched chain or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but preferably the number of carbon atoms is 1 to 20. Specifically, it may be a methoxy group, an ethoxy group, a n-propoxy group, an isopropoxy group, a n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, a n-pentoxy group, a neopentoxy group, an isopentyl group, a n-hexyl group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, a n-octyloxy group, a n-nonyloxy group, a n-decyloxy group, etc., but is not limited thereto.

[0050] The alkyl group, alkoxy group, and other substituents containing an alkyl portion described in the present specification include all of linear and branched forms.

[0051] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. As specific examples, there are 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-(naphthalene-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbene, styryl, etc., but are not limited thereto.

[0052] In the present specification, the alkynyl group is a substituent containing a triple bond between carbon atoms, and may be a linear or branched chain, 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 in the alkynyl group is 2 to 20. According to another embodiment, the number of carbon atoms in the alkynyl group is 2 to 10.

[0053] In the present specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group having 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 another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, there are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., but are not limited thereto.

[0054] In the present specification, the amino group is -NH2, and the above-mentioned amino group may be substituted with the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The number of carbon atoms of the above-mentioned substituted amino group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the number of carbon atoms of the above-mentioned amino group is 1 to 20. According to one embodiment, the number of carbon atoms of the above-mentioned amino group is 1 to 10. As specific examples of substituted amino groups, there are methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, 9,9-dimethylfluorenylphenylamino, pyridylphenylamino, diphenylamino, phenylpyridylamino, naphthylamino, biphenylamino, anthracenylamino, dibenzofuranylphenylamino, 9-methylanthrylamino, diphenylamino, phenylnaphthylamino, ditolylamino, phenyltolylamino, diphenylamino, etc., but are not limited thereto.

[0055] In the present specification, the aryl group is not particularly limited, but is preferably an aryl group having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 30. According to one embodiment, the carbon number of the aryl group is 6 to 20. Regarding the aryl group, as a monocyclic aryl group, it may be phenyl, biphenyl, terphenyl, quaterphenyl, etc., but it is not limited thereto. As the polycyclic aryl group, it may be naphthyl, anthracenyl, phenanthrenyl, pyrenyl, perylenyl, triphenyl, phenylene, fluorenyl, triphenylene, etc., but are not limited to these.

[0056] In the present specification, the fluorenyl group may be substituted, and two substituents may be combined with each other to form a spiro structure. In this case, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

[0057] When the fluorenyl group is substituted, it may be Isospirofluorenyl; (9,9-dimethylfluorenyl) and (9,9-diphenylfluorenyl) and the like substituted fluorenyl, but the present invention is not limited thereto.

[0058] In the present specification, the above description on the aryl group can be applied to the aryl group in the aryloxy group.

[0059] In the present specification, the above description about the alkyl group can be applied to the alkyl group in the above alkylthio group and alkylsulfonyl group.

[0060] In the present specification, the above description about the aryl group can be applied to the aryl group in the arylthio group and the arylsulfonyl group.

[0061] In the present specification, the heterocyclic group is a ring group containing one or more of N, O, P, S, Si and Se as heteroatoms, and the number of carbon atoms is not particularly limited, but preferably the number of carbon atoms is 2 to 60. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms in the heterocyclic group is 2 to 20. Examples of the heterocyclic group include pyridyl, pyrrolyl, pyrimidinyl, quinolyl, pyridazinyl, furyl, thienyl, imidazolyl, pyrazolyl, dibenzofuranyl, dibenzothienyl, carbazolyl, benzocarbazolyl, naphthobenzofuranyl, benzonaphthothienyl, indenocarbazolyl, triazinyl and the like, but are not limited thereto.

[0062] In the present specification, a heteroaryl group is aromatic, and other than this, the above description about the heterocyclic group is applicable.

[0063] In the present specification, the description of the above-mentioned aryl group is applicable to the above-mentioned arylene group except that the above-mentioned arylene group is divalent.

[0064] In the present specification, the same explanation as for the above-mentioned heterocyclic group can be applied to the divalent heterocyclic ring except that the divalent heterocyclic ring is divalent.

[0065] In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups, "ring" means a hydrocarbon ring or a heterocyclic ring.

[0066] The hydrocarbon ring may be aromatic, aliphatic, or a condensed ring of aromatic and aliphatic groups, and may be selected from the examples of the cycloalkyl group or aryl group described above.

[0067] In this specification, the meaning of forming a ring by combining with adjacent groups means combining with adjacent groups to form 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 condensed ring thereof. The above hydrocarbon ring refers to a ring consisting only of carbon and hydrogen atoms. The above heterocycle refers to a ring containing one or more elements selected from N, O, P, S, Si and Se. In this specification, the above aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle and aromatic heterocycle can be monocyclic or polycyclic.

[0068] In this specification, an aliphatic hydrocarbon ring refers to a ring that is not an aromatic ring and is composed only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene.

[0069] In this specification, an aromatic hydrocarbon ring refers to an aromatic ring composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenanthene, pyrene, tetracene, In the present specification, the aromatic hydrocarbon ring can be interpreted as having the same meaning as the aryl group.

[0070] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, 1,4-dihydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane Azoctane Thioctane etc., but not limited thereto.

[0071] In the present 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, Azoles, Isopropylamine Azoles, thiazoles, isothiazoles, triazoles, diazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, pyridazine, Azine, thiazine, di Olefins, triazines, tetrazines, isoquinolines, quinolines, quinones, quinazolines, quinoxalines, naphthyridines, acridines, phenanthridines, naphthyridines, triazaindene, indoles, indolizines, benzothiazoles, benzo azole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phen Oxazine, indolecarbazole, indenocarbazole, etc., but are not limited to these.

[0072] Hereinafter, preferred embodiments of the present invention will be described in detail. However, the embodiments of the present invention can be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.

[0073] According to the compound represented by Chemical Formula 1 of the present invention, by connecting carbazole and amine with a terphenyl linking group (meta-ortho direction), the HOMO and LUMO energies of the compound are appropriately adjusted as the conjugation length of the compound is adjusted. When the compound of Chemical Formula 1 is applied to an organic light-emitting device, the effects of low voltage, high efficiency and / or long life can be exhibited.

[0074] In addition, the compound represented by Chemical Formula 1 according to the present invention is substituted or unsubstituted with deuterium through the terphenyl linking group (meta-ortho direction) between carbazole and amine, thereby showing the effect of regulating the barrier with the adjacent organic layer compared with the compound into which the terphenyl linking group substituted with an aryl group or a heteroaryl group is introduced.

[0075] In addition, when the carbazole of the compound represented by Chemical Formula 1 according to the present invention is connected to the terphenyl linking group (meta-ortho direction) in a meta orientation, and the terphenyl linking group (meta-ortho direction) is connected to the amine in an ortho orientation or a meta orientation, compared with the compound in which the terphenyl linking group (meta-ortho direction) is connected to the amine group in a para orientation, the effect of improving the hole migration characteristics can be shown.

[0076] Therefore, when the compound represented by the above Chemical Formula 1 is applied to an organic light-emitting device, an organic light-emitting device having high efficiency, low voltage and / or long life characteristics may be obtained.

[0077] Next, Chemical Formula 1 will be described in detail.

[0078] [Chemical formula 1]

[0079]

[0080] In the above chemical formula 1,

[0081] Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted cycloalkyl group,

[0082] L1 to L3 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group,

[0083] R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0084] R3 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted silyl group, an unsubstituted aryl group having 10 to 30 carbon atoms, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylalkenyl group, or a substituted or unsubstituted heterocyclic group containing O or S,

[0085] a to e are integers of 1 to 4, and when a to e is 2 or more, two or more R1 to R5 are the same or different from each other,

[0086] p to r are integers of 1 to 4, and when p to r is 2 or more, two or more L1 to L3 are the same as or different from each other.

[0087] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted polycyclic aryl group having 10 or more carbon atoms.

[0088] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted polycyclic aryl group having 10 to 60 carbon atoms.

[0089] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted polycyclic aryl group having 10 to 30 carbon atoms.

[0090] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted polycyclic aryl group having 10 to 20 carbon atoms.

[0091] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted monocyclic aryl group having 6 or more carbon atoms.

[0092] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted monocyclic aryl group having 6 to 10 carbon atoms.

[0093] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted bicyclic or more aryl group having 10 or more carbon atoms.

[0094] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted bicyclic or more aromatic group having 10 to 60 carbon atoms.

[0095] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted bicyclic or more aromatic group having 10 to 30 carbon atoms.

[0096] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted bicyclic or higher aromatic group having 10 to 20 carbon atoms.

[0097] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted bicyclic to tetracyclic aryl group having 10 to 20 carbon atoms.

[0098] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted bicyclic or tricyclic aryl group having 10 to 20 carbon atoms.

[0099] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted adamantyl group.

[0100] In one embodiment of the present specification, Ar1 is a phenyl group substituted or unsubstituted by deuterium, a biphenyl group substituted or unsubstituted by deuterium, a terphenyl group substituted or unsubstituted by deuterium, a naphthyl group substituted or unsubstituted by deuterium, an anthracenyl group substituted or unsubstituted by deuterium, a phenanthryl group substituted or unsubstituted by deuterium, a triphenylene group substituted or unsubstituted by deuterium, a fluorenyl group substituted or unsubstituted by deuterium, a carbazolyl group substituted or unsubstituted by deuterium, a dibenzothiophenyl group substituted or unsubstituted by deuterium, a dibenzofuranyl group substituted or unsubstituted by deuterium, or an adamantyl group substituted or unsubstituted by deuterium.

[0101] In one embodiment of the present specification, Ar1 is a phenyl group substituted or unsubstituted by at least one of the group consisting of deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a biphenyl group substituted or unsubstituted by at least one of the group consisting of deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a phenyl group substituted or unsubstituted by at least one of the group consisting of deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted terphenyl group; a naphthyl group substituted or unsubstituted by at least one of the group consisting of deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; an anthracenyl group substituted or unsubstituted by at least one of the group consisting of deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; an anthracenyl group substituted or unsubstituted by at least one of the group consisting of deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms Phenanthryl; triphenylene substituted or unsubstituted by at least one of the group consisting of deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; fluorenyl substituted or unsubstituted by at least one of the group consisting of deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; carbazolyl substituted or unsubstituted by at least one of the group consisting of deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; , a dibenzothiophenyl group which is substituted or unsubstituted by at least one of the group consisting of a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuranyl group which is substituted or unsubstituted by at least one of the group consisting of deuterium, a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or an adamantyl group which is substituted or unsubstituted by at least one of the group consisting of deuterium, a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0102] In one embodiment of the present specification, Ar1 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, or substituted or unsubstituted adamantyl.

[0103] In one embodiment of the present specification, Ar1 is a deuterium-substituted or unsubstituted phenyl group, a deuterium-substituted or unsubstituted biphenyl group, a deuterium-substituted or unsubstituted terphenyl group, a deuterium-substituted or unsubstituted naphthyl group, a deuterium-substituted or unsubstituted anthracenyl group, a deuterium-substituted or unsubstituted phenanthrenyl group, or a deuterium-substituted or unsubstituted adamantyl group.

[0104] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group.

[0105] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group.

[0106] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted phenyl group.

[0107] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted biphenyl group.

[0108] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted terphenyl group.

[0109] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0110] In one embodiment of the present specification, Ar1 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.

[0111] In one embodiment of the present specification, Ar1 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.

[0112] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group containing O, S or N having 2 to 60 carbon atoms.

[0113] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group containing O, S or N having 2 to 30 carbon atoms.

[0114] In one embodiment of the present specification, Ar1 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group containing O, S or N having 2 to 20 carbon atoms.

[0115] In one embodiment of the present specification, Ar1 is an aryl group having 6 to 60 carbon atoms, which is unsubstituted or substituted by deuterium or an aryl group having 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N, which is unsubstituted or substituted by deuterium or an aryl group having 6 to 30 carbon atoms and has 2 to 60 carbon atoms.

[0116] In one embodiment of the present specification, Ar1 is an aryl group having 6 to 60 carbon atoms, which is unsubstituted or substituted with at least one of the group consisting of deuterium, a straight chain or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N having 2 to 60 carbon atoms, which is unsubstituted or substituted with deuterium or an aryl group having 6 to 30 carbon atoms.

[0117] In one embodiment of the present specification, Ar1 is an aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted by deuterium or an aryl group having 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N having 2 to 30 carbon atoms which is unsubstituted or substituted by deuterium or an aryl group having 6 to 30 carbon atoms.

[0118] In one embodiment of the present specification, Ar1 is an aryl group having 6 to 30 carbon atoms, which is unsubstituted or substituted with at least one of the group consisting of deuterium, a straight chain or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N having 2 to 30 carbon atoms, which is unsubstituted or substituted with deuterium or an aryl group having 6 to 30 carbon atoms.

[0119] In one embodiment of the present specification, Ar1 is an aryl group having 6 to 20 carbon atoms which is unsubstituted or substituted by deuterium or an aryl group having 6 to 20 carbon atoms; or a heterocyclic group containing O, S or N having 2 to 20 carbon atoms which is unsubstituted or substituted by deuterium or an aryl group having 6 to 20 carbon atoms.

[0120] In one embodiment of the present specification, Ar1 is an aryl group having 6 to 20 carbon atoms, which is unsubstituted or substituted with at least one of the group consisting of deuterium, a straight or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N having 2 to 20 carbon atoms, which is unsubstituted or substituted with deuterium or an aryl group having 6 to 20 carbon atoms.

[0121] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted polycyclic aryl group having 10 or more carbon atoms.

[0122] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted polycyclic aryl group having 10 to 60 carbon atoms.

[0123] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted polycyclic aryl group having 10 to 30 carbon atoms.

[0124] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted polycyclic aryl group having 10 to 20 carbon atoms.

[0125] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted monocyclic aryl group having 6 or more carbon atoms.

[0126] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted monocyclic aryl group having 6 to 10 carbon atoms.

[0127] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted bicyclic or higher aryl group having 10 or more carbon atoms.

[0128] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted bicyclic or higher aromatic group having 10 to 60 carbon atoms.

[0129] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted bicyclic or higher aromatic group having 10 to 30 carbon atoms.

[0130] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted bicyclic or higher aromatic group having 10 to 20 carbon atoms.

[0131] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted bicyclic to tetracyclic aryl group having 10 to 20 carbon atoms.

[0132] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted bicyclic or tricyclic aryl group having 10 to 20 carbon atoms.

[0133] In one embodiment of the present specification, Ar2 is substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted adamantyl.

[0134] In one embodiment of the present specification, Ar2 is a phenyl group substituted or unsubstituted by deuterium, a biphenyl group substituted or unsubstituted by deuterium, a terphenyl group substituted or unsubstituted by deuterium, a naphthyl group substituted or unsubstituted by deuterium, an anthracenyl group substituted or unsubstituted by deuterium, a phenanthryl group substituted or unsubstituted by deuterium, a triphenylene group substituted or unsubstituted by deuterium, a fluorenyl group substituted or unsubstituted by deuterium, a carbazolyl group substituted or unsubstituted by deuterium, a dibenzothiophene group substituted or unsubstituted by deuterium, a dibenzofuranyl group substituted or unsubstituted by deuterium, or an adamantyl group substituted or unsubstituted by deuterium.

[0135] In one embodiment of the present specification, Ar2 is a phenyl group which is substituted or unsubstituted by at least one of the group consisting of deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a biphenyl group which is substituted or unsubstituted by at least one of the group consisting of deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a phenyl group which is substituted or unsubstituted by at least one of the group consisting of deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted terphenyl group; a naphthyl group substituted or unsubstituted by at least one of the group consisting of deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; an anthracenyl group substituted or unsubstituted by at least one of the group consisting of deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; an anthracenyl group substituted or unsubstituted by at least one of the group consisting of deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms Phenanthryl; triphenylene substituted or unsubstituted by at least one of the group consisting of deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; fluorenyl substituted or unsubstituted by at least one of the group consisting of deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; carbazolyl substituted or unsubstituted by at least one of the group consisting of deuterium, a linear or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; , a dibenzothiophenyl group which is substituted or unsubstituted by at least one of the group consisting of a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuranyl group which is substituted or unsubstituted by at least one of the group consisting of deuterium, a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or an adamantyl group which is substituted or unsubstituted by at least one of the group consisting of deuterium, a straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms and a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0136] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted adamantyl group.

[0137] In one embodiment of the present specification, Ar2 is a phenyl group substituted or unsubstituted by deuterium, a biphenyl group substituted or unsubstituted by deuterium, a terphenyl group substituted or unsubstituted by deuterium, a naphthyl group substituted or unsubstituted by deuterium, an anthracenyl group substituted or unsubstituted by deuterium, a phenanthrenyl group substituted or unsubstituted by deuterium, or an adamantyl group substituted or unsubstituted by deuterium.

[0138] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group.

[0139] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted naphthyl group.

[0140] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted phenyl group.

[0141] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted biphenyl group.

[0142] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted terphenyl group.

[0143] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0144] In one embodiment of the present specification, Ar2 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.

[0145] In one embodiment of the present specification, Ar2 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.

[0146] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group containing O, S or N having 2 to 60 carbon atoms.

[0147] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group containing O, S or N having 2 to 30 carbon atoms.

[0148] In one embodiment of the present specification, Ar2 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group containing O, S or N having 2 to 20 carbon atoms.

[0149] In one embodiment of the present specification, Ar2 is an aryl group having 6 to 60 carbon atoms, which is unsubstituted or substituted by deuterium or an aryl group having 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N, which is unsubstituted or substituted by deuterium or an aryl group having 6 to 30 carbon atoms and has 2 to 60 carbon atoms.

[0150] In one embodiment of the present specification, Ar2 is an aryl group having 6 to 60 carbon atoms, which is unsubstituted or substituted by at least one of the group consisting of deuterium, a straight chain or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N having 2 to 60 carbon atoms, which is unsubstituted or substituted by deuterium or an aromatic group having 6 to 30 carbon atoms.

[0151] In one embodiment of the present specification, Ar2 is an aryl group having 6 to 30 carbon atoms, which is unsubstituted or substituted by deuterium or an aryl group having 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N having 2 to 30 carbon atoms, which is unsubstituted or substituted by deuterium or an aryl group having 6 to 30 carbon atoms.

[0152] In one embodiment of the present specification, Ar2 is an aryl group having 6 to 30 carbon atoms, which is unsubstituted or substituted by at least one of the group consisting of deuterium, a straight chain or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N having 2 to 30 carbon atoms, which is unsubstituted or substituted by deuterium or an aromatic group having 6 to 30 carbon atoms.

[0153] In one embodiment of the present specification, Ar2 is an aryl group having 6 to 20 carbon atoms, which is unsubstituted or substituted by deuterium or an aryl group having 6 to 20 carbon atoms; or a heterocyclic group containing O, S or N, which is unsubstituted or substituted by deuterium or an aryl group having 6 to 20 carbon atoms.

[0154] In one embodiment of the present specification, Ar2 is an aryl group having 6 to 20 carbon atoms, which is unsubstituted or substituted by at least one of the group consisting of deuterium, a straight chain or branched alkyl group having 1 to 30 carbon atoms, and a monocyclic or polycyclic aromatic group having 6 to 30 carbon atoms; or a heterocyclic group containing O, S or N having 2 to 20 carbon atoms, which is unsubstituted or substituted by deuterium or an aromatic group having 6 to 20 carbon atoms.

[0155] In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other.

[0156] In one embodiment of the present specification, Ar1 and Ar2 are the same as each other.

[0157] In one embodiment of the present specification, Ar1 and Ar2 are different.

[0158] In one embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group.

[0159] In one embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.

[0160] In one embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

[0161] In one embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 20 carbon atoms.

[0162] In one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group containing O, S or N having 2 to 60 carbon atoms.

[0163] In one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group containing O, S or N having 2 to 30 carbon atoms.

[0164] In one embodiment of the present specification, L1 is a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group containing O, S or N having 2 to 20 carbon atoms.

[0165] In one embodiment of the present specification, L1 is a direct bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0166] In one embodiment of the present specification, L1 is an arylene group having 6 to 30 carbon atoms which is directly bonded or substituted or unsubstituted with deuterium.

[0167] In one embodiment of the present specification, L1 is an arylene group having 6 to 20 carbon atoms which is directly bonded or substituted or unsubstituted with deuterium.

[0168] In one embodiment of the present specification, L1 is a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0169] In one embodiment of the present specification, L1 is a direct bond, a phenylene group which may be substituted by deuterium, or a biphenylene group which may be substituted by deuterium.

[0170] In one embodiment of the present specification, L1 is a direct bond, a phenylene group, or a biphenylene group.

[0171] In one embodiment of the present specification, L1 is a direct bond.

[0172] In one embodiment of the present specification, L1 is a substituted or unsubstituted phenylene group.

[0173] In one embodiment of the present specification, L2 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group.

[0174] In one embodiment of the present specification, L2 is a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.

[0175] In one embodiment of the present specification, L2 is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

[0176] In one embodiment of the present specification, L2 is a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 20 carbon atoms.

[0177] In one embodiment of the present specification, L2 is a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group containing O, S or N having 2 to 60 carbon atoms.

[0178] In one embodiment of the present specification, L2 is a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group containing O, S or N having 2 to 30 carbon atoms.

[0179] In one embodiment of the present specification, L2 is a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group containing O, S or N having 2 to 20 carbon atoms.

[0180] In one embodiment of the present specification, L2 is a direct bond, or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0181] In one embodiment of the present specification, L2 is an arylene group having 6 to 30 carbon atoms which is directly bonded or substituted or unsubstituted with deuterium.

[0182] In one embodiment of the present specification, L2 is an arylene group having 6 to 20 carbon atoms which is directly bonded or substituted or unsubstituted with deuterium.

[0183] In one embodiment of the present specification, L2 is a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0184] In one embodiment of the present specification, L2 is a direct bond, a phenylene group which may be substituted by deuterium, or a biphenylene group which may be substituted by deuterium.

[0185] In one embodiment of the present specification, L2 is a direct bond, a phenylene group, or a biphenylene group.

[0186] In one embodiment of the present specification, L2 is a direct bond.

[0187] In one embodiment of the present specification, L2 is a substituted or unsubstituted phenylene group.

[0188] In one embodiment of the present specification, L3 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group.

[0189] In one embodiment of the present specification, L3 is a direct bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 60 carbon atoms.

[0190] In one embodiment of the present specification, L3 is a direct bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 30 carbon atoms.

[0191] In one embodiment of the present specification, L3 is a direct bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 2 to 20 carbon atoms.

[0192] In one embodiment of the present specification, L3 is a direct bond; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group containing O, S or N having 2 to 60 carbon atoms.

[0193] In one embodiment of the present specification, L3 is a direct bond; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group containing O, S or N having 2 to 30 carbon atoms.

[0194] In one embodiment of the present specification, L3 is a direct bond; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted divalent heterocyclic group containing O, S or N having 2 to 20 carbon atoms.

[0195] In one embodiment of the present specification, L3 is a direct bond or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0196] In one embodiment of the present specification, L3 is an arylene group having 6 to 30 carbon atoms which is directly bonded or substituted or unsubstituted with deuterium.

[0197] In one embodiment of the present specification, L3 is an arylene group having 6 to 20 carbon atoms which is directly bonded or substituted or unsubstituted with deuterium.

[0198] In one embodiment of the present specification, L3 is a direct bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted biphenylene group.

[0199] In one embodiment of the present specification, L3 is a direct bond, a phenylene group which may be substituted by deuterium, or a biphenylene group which may be substituted by deuterium.

[0200] In one embodiment of the present specification, L3 is a direct bond, a phenylene group, or a biphenylene group.

[0201] In one embodiment of the present specification, L3 is a direct bond.

[0202] In one embodiment of the present specification, L3 is a substituted or unsubstituted phenylene group.

[0203] In one embodiment of the present specification, L1 to L3 are the same as or different from each other.

[0204] In one embodiment of the present specification, L1 to L3 are identical to each other.

[0205] In one embodiment of the present specification, L1 to L3 are different.

[0206] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0207] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.

[0208] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.

[0209] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, or a substituted or unsubstituted heterocyclic group having 2 to 20 carbon atoms.

[0210] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted arylene group having 6 to 60 carbon atoms; or a substituted or unsubstituted heterocyclic group containing O, S or N and having 2 to 60 carbon atoms.

[0211] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group containing O, S or N and having 2 to 30 carbon atoms.

[0212] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heterocyclic group containing O, S or N and having 2 to 20 carbon atoms.

[0213] In one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0214] In one embodiment of the present specification, R1 and R2 are both hydrogen.

[0215] In one embodiment of the present specification, both R1 and R2 are deuterium.

[0216] In one embodiment of the present specification, R1 is hydrogen.

[0217] In one embodiment of the present specification, R1 is deuterium.

[0218] In one embodiment of the present specification, R2 is hydrogen.

[0219] In one embodiment of the present specification, R2 is deuterium.

[0220] In one embodiment of the present specification, R3 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylalkenyl group, or a substituted or unsubstituted heterocyclic group containing O or S.

[0221] In one embodiment of the present specification, R3 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylalkenyl group, or a substituted or unsubstituted heterocyclic group containing O or S having 10 to 30 carbon atoms.

[0222] In one embodiment of the present specification, R3 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylalkenyl group, or a substituted or unsubstituted heterocyclic group containing O or S having 10 to 20 carbon atoms.

[0223] In one embodiment of the present specification, R3 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylalkenyl group, or a substituted or unsubstituted heterocyclic group containing O and having 10 to 30 carbon atoms.

[0224] In one embodiment of the present specification, R3 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylalkenyl group, or a substituted or unsubstituted heterocyclic group containing S having 10 to 30 carbon atoms.

[0225] In one embodiment of the present specification, R3 to R5 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0226] In one embodiment of the present specification, R3 to R6 are all hydrogen.

[0227] In one embodiment of the present specification, R3 to R6 are all deuterium.

[0228] In one embodiment of the present specification, R3 is hydrogen.

[0229] In one embodiment of the present specification, R3 is deuterium.

[0230] In one embodiment of the present specification, R4 is hydrogen.

[0231] In one embodiment of the present specification, R4 is deuterium.

[0232] In one embodiment of the present specification, R5 is hydrogen.

[0233] In one embodiment of the present specification, R5 is deuterium.

[0234] In one embodiment of the present specification, a to e are each an integer of 1 to 4, and when a to e are 2 or more, two or more R1 to R5 are each the same as or different from each other.

[0235] In one embodiment of the present specification, a to e are integers of 1 to 4.

[0236] In one embodiment of the present specification, a to e are each 1.

[0237] In one embodiment of the present specification, a to e are each 2.

[0238] In one embodiment of the present specification, a to e are each 3.

[0239] In one embodiment of the present specification, a to e are each 4.

[0240] In one embodiment of the present specification, p to r are each an integer of 1 to 4, and when p to r are 2 or more, two or more L1 to L3 are each the same as or different from each other.

[0241] In one embodiment of the present specification, p to q are integers of 1 to 4, respectively.

[0242] In one embodiment of the present specification, p to r are each an integer from 1 to 4.

[0243] In one embodiment of the present specification, p to r are each 1.

[0244] In one embodiment of the present specification, p to r are each 2.

[0245] In one embodiment of the present specification, p to r are each 3.

[0246] In one embodiment of the present specification, p to r are each 4.

[0247] In one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1 to 1-3.

[0248] [Chemical formula 1-1]

[0249]

[0250] [Chemical formula 1-2]

[0251]

[0252] [Chemical formula 1-3]

[0253]

[0254] In the above chemical formulas 1-1 to 1-3,

[0255] Definitions of Ar1, Ar2, L1 to L3, R1 to R5, a to e, and p to r are the same as those in the above Chemical Formula 1.

[0256] In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0257] In one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted adamantyl group.

[0258] In one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1 to 2-6.

[0259] [Chemical formula 2-1]

[0260]

[0261] [Chemical formula 2-2]

[0262]

[0263] [Chemical formula 2-3]

[0264]

[0265] [Chemical formula 2-4]

[0266]

[0267] [Chemical formula 2-5]

[0268]

[0269] [Chemical formula 2-6]

[0270]

[0271] In the above chemical formulas 2-1 to 2-6,

[0272] Ar1, Ar2, L1 to L3, R1 to R5, a to e and p to r are defined as in the above Chemical Formula 1,

[0273] D is deuterium,

[0274] f1 to f3 are 0 to 4, respectively.

[0275] In one embodiment of the present specification, f1 is 0.

[0276] In one embodiment of the present specification, f1 is 1.

[0277] In one embodiment of the present specification, f1 is 2.

[0278] In one embodiment of the present specification, f1 is 3.

[0279] In one embodiment of the present specification, f1 is 4.

[0280] In one embodiment of the present specification, f2 is 0.

[0281] In one embodiment of the present specification, f2 is 1.

[0282] In one embodiment of the present specification, f2 is 2.

[0283] In one embodiment of the present specification, f2 is 3.

[0284] In one embodiment of the present specification, f2 is 4.

[0285] In one embodiment of the present specification, f3 is 0.

[0286] In one embodiment of the present specification, f3 is 1.

[0287] In one embodiment of the present specification, f3 is 2.

[0288] In one embodiment of the present specification, f3 is 3.

[0289] In one embodiment of the present specification, f3 is 4.

[0290] In one embodiment of the present specification, L1 to L3 are the same as or different from each other, and each is a directly bonded or substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0291] In one embodiment of the present specification, the above Chemical Formula 1 is represented by the following Chemical Formula 3.

[0292] [Chemical formula 3]

[0293]

[0294] In the above chemical formula 3,

[0295] Ar1, Ar2, R1 to R5, and a to e are defined as in the above Chemical Formula 1.

[0296] D is deuterium,

[0297] x1 to x3 are 0 to 4, respectively,

[0298] s1 to s3 are 0 or 1, respectively.

[0299] In one embodiment of the present specification, x1 is 0.

[0300] In one embodiment of the present specification, x1 is 1.

[0301] In one embodiment of the present specification, x1 is 2.

[0302] In one embodiment of the present specification, x1 is 3.

[0303] In one embodiment of the present specification, x1 is 4.

[0304] In one embodiment of the present specification, x2 is 0.

[0305] In one embodiment of the present specification, x2 is 1.

[0306] In one embodiment of the present specification, x2 is 2.

[0307] In one embodiment of the present specification, x2 is 3.

[0308] In one embodiment of the present specification, x2 is 4.

[0309] In one embodiment of the present specification, x3 is 0.

[0310] In one embodiment of the present specification, x3 is 1.

[0311] In one embodiment of the present specification, x3 is 2.

[0312] In one embodiment of the present specification, x3 is 3.

[0313] In one embodiment of the present specification, x3 is 4.

[0314] In one embodiment of the present specification, s1 is 0.

[0315] In one embodiment of the present specification, s1 is 1.

[0316] In one embodiment of the present specification, s2 is 0.

[0317] In one embodiment of the present specification, s2 is 1.

[0318] In one embodiment of the present specification, s3 is 0.

[0319] In one embodiment of the present specification, s3 is 1.

[0320] In one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 3-1 to 3-3.

[0321] [Chemical formula 3-1]

[0322]

[0323] [Chemical formula 3-2]

[0324]

[0325] [Chemical formula 3-3]

[0326]

[0327] In the above chemical formulas 3-1 to 3-3,

[0328] Ar1, Ar2, R1 to R5 and a to e are defined as in the above Chemical Formula 1,

[0329] D is deuterium,

[0330] x1 to x3 are 0 to 4, respectively,

[0331] s1 to s3 are 0 or 1, respectively.

[0332] In one embodiment of the present specification, R1 to R5 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0333] In one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following Chemical Formulas 4-1 to 4-4.

[0334]

[0335]

[0336] In the above chemical formulas 4-1 to 4-4,

[0337] Ar1, Ar2, L1, L3, R1 to R5, a to e, p and r are defined as in the above Chemical Formula 1,

[0338] D is deuterium,

[0339] x4 and x5 are 0 to 4 respectively,

[0340] y is 0 to 5,

[0341] z is 0 to 7.

[0342] In one embodiment of the present specification, x4 is 0.

[0343] In one embodiment of the present specification, x4 is 1.

[0344] In one embodiment of the present specification, x4 is 2.

[0345] In one embodiment of the present specification, x4 is 3.

[0346] In one embodiment of the present specification, x4 is 4.

[0347] In one embodiment of the present specification, x5 is 0.

[0348] In one embodiment of the present specification, x5 is 1.

[0349] In one embodiment of the present specification, x5 is 2.

[0350] In one embodiment of the present specification, x5 is 3.

[0351] In one embodiment of the present specification, x5 is 4.

[0352] In one embodiment of the present specification, y is 0.

[0353] In one embodiment of the present specification, y is 1.

[0354] In one embodiment of the present specification, y is 2.

[0355] In one embodiment of the present specification, y is 3.

[0356] In one embodiment of the present specification, y is 4.

[0357] In one embodiment of the present specification, y is 5.

[0358] In one embodiment of the present specification, z is 0.

[0359] In one embodiment of the present specification, z is 1.

[0360] In one embodiment of the present specification, z is 2.

[0361] In one embodiment of the present specification, z is 3.

[0362] In one embodiment of the present specification, z is 4.

[0363] In one embodiment of the present specification, z is 5.

[0364] In one embodiment of the present specification, z is 6.

[0365] In one embodiment of the present specification, z is 7.

[0366] In one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following compounds.

[0367]

[0368]

[0369]

[0370]

[0371]

[0372]

[0373]

[0374]

[0375]

[0376]

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386]

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395] In one embodiment of the present specification, the above Chemical Formula 1 is represented by any one of the following compounds.

[0396]

[0397]

[0398] Among the above compounds,

[0399] D is deuterium,

[0400] n is an integer of 1 or more.

[0401] n is the number of deuterium substitutions. The number of deuterium substitutions in the above-mentioned compounds is 1 or more and 40 or less at most.

[0402]

[0403]

[0404] For example, D1 in the compound D-1 means that a position replaceable by hydrogen is substituted with one deuterium. Chemical formula D-1 is just one of the examples, and the position substituted with deuterium is not limited to the examples.

[0405] D of the above compound D-40 40 The meaning of is that the positions which can be replaced by hydrogen are substituted with 40 deuteriums, and the chemical formula D-40 is one of the examples.

[0406] The compound represented by Chemical Formula 1 according to one embodiment of the present specification can produce a core structure as shown in the following Reaction Formula 1. Substituents can be bonded by methods known in the art, and the type, position or number of substituents can be changed according to techniques known in the art.

[0407] Reaction 1

[0408]

[0409] In the above reaction formula 1, X can be a halogen group such as Cl, Br, I, etc.

[0410] In the present specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by the above Chemical Formula 1. In addition, in the present specification, the HOMO and LUMO energy levels of the compound can also be adjusted by introducing various substituents into the core structure of the structure shown above.

[0411] In addition, the present specification provides an organic light-emitting device including the above-mentioned compound.

[0412] In the present specification, when it is mentioned that a certain component is located “on” another component, it not only includes the case where the certain component is in contact with the other component, but also includes the case where other components exist between the two components.

[0413] In the present specification, when it is indicated that a certain part “includes / comprises” a certain constituent element, unless there is a particular description to the contrary, it means that other constituent elements may be further included, rather than excluding other constituent elements.

[0414] The organic light-emitting device according to the present specification is characterized by comprising: 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 contains the compound represented by the above Chemical Formula 1.

[0415] The organic light-emitting device of the present specification uses the compound of Chemical Formula 1 to form an organic layer, and can also be manufactured using a common method and material for manufacturing an organic light-emitting device.

[0416] The above compounds can be formed into an organic layer by not only vacuum evaporation method but also solution coating method when manufacturing organic light-emitting devices. Here, the so-called solution coating method refers to spin coating method, dip coating method, inkjet printing method, screen printing method, spray method, roller coating method, etc., but is not limited to these.

[0417] The organic layer of the organic light-emitting device of the present specification may be formed by a single-layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure including 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 one or more of the electron transport and injection layers as organic layers. However, the structure of the organic light-emitting device of the present specification is not limited thereto and may include a smaller number or a larger number of organic layers.

[0418] In the organic light-emitting device of the present specification, the organic light-emitting device includes a light-emitting layer, and the organic layer including the compound represented by the above Chemical Formula 1 may be located between the above anode and the light-emitting layer.

[0419] In the organic light-emitting device of the present 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, the hole transport layer, or the hole injection and transport layer may contain the compound represented by the above Chemical Formula 1.

[0420] In the organic light-emitting device of the present specification, the organic layer includes a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer may include the compound represented by the above Chemical Formula 1.

[0421] In one embodiment of the present specification, the organic layer includes an electron blocking layer, and the electron blocking layer includes the compound represented by Chemical Formula 1.

[0422] In one embodiment of the present specification, the organic 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 may contain the compound represented by the above-mentioned Chemical Formula 1.

[0423] In the organic light-emitting device of the present 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, the electron injection layer, or the electron transport and injection layer may contain the compound represented by the above Chemical Formula 1.

[0424] In one embodiment of the present specification, the organic layer includes an electron adjustment layer, and the electron adjustment layer may include the compound represented by the above Chemical Formula 1.

[0425] In one embodiment of the present specification, the organic layer includes a hole blocking layer, and the hole blocking layer includes the compound represented by Chemical Formula 1.

[0426] In the organic light-emitting device of the present specification, the organic layer is an electron transport and injection layer, and the electron transport and injection layer includes the compound represented by the above Chemical Formula 1.

[0427] In one embodiment of the present specification, the thickness of the organic layer containing the compound of the above Chemical Formula 1 is to Preferably to More preferably to

[0428] The organic light-emitting device of the present specification may further include 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 one or more organic layers among the hole transport and injection layer.

[0429] In one embodiment of the present specification, the organic light-emitting device includes: an anode, a cathode, and two or more organic layers disposed between the anode and the cathode, and at least one of the two or more organic layers contains the compound represented by the chemical formula 1.

[0430] In one embodiment of the present specification, the two or more organic 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.

[0431] In one embodiment of the present specification, the two or more organic layers may be selected from the group consisting of a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron regulating layer, and a hole blocking layer.

[0432] In one embodiment of the present specification, the organic layer includes two or more electron transport layers, and at least one of the two or more electron transport layers contains the compound represented by the chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by the chemical formula 1 may be contained in one of the two or more electron transport layers, or in each of the two or more electron transport layers.

[0433] In one embodiment of the present specification, when the compound is included in each of the two or more electron transport layers, materials other than the compound represented by the chemical formula 1 may be the same as or different from each other.

[0434] 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 above electron transport layer, the electron injection layer, or the electron transport and injection layer may further include an n-type dopant. The above n-type dopant may use materials known in the art, for example, a metal or a metal complex may be used. For example, the electron transport layer containing the compound represented by the above chemical formula 1 may further include LiQ (LithiumQuinolate, quinoline lithium). According to an example, the compound represented by the above chemical formula 1 and the above n-type dopant may be included in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.

[0435] According to an example, the compound represented by the above Chemical Formula 1 and the above n-type dopant may be included in a weight ratio of 1:1.

[0436] In one embodiment of the present specification, the organic layer includes two or more hole transport layers, and at least one of the two or more hole transport layers includes the compound represented by the chemical formula 1. Specifically, in one embodiment of the present specification, the compound represented by the chemical formula 1 may be included in one of the two or more hole transport layers, or may be included in each of the two or more hole transport layers.

[0437] In one embodiment of the present specification, when the compound represented by the above Chemical Formula 1 is included in each of the two or more hole transport layers, materials other than the compound represented by the above Chemical Formula 1 may be the same as or different from each other.

[0438] In one embodiment of the present specification, the organic layer may include a hole injection layer or a hole transport layer in addition to the organic layer including the compound represented by the above Chemical Formula 1, wherein the hole injection layer or the hole transport layer includes a compound containing an arylamine group, a carbazole group or a benzocarbazole group.

[0439] In one embodiment of the present specification, the organic light-emitting device may be a (normal type) organic light-emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.

[0440] In one embodiment of the present specification, the organic light emitting device may be an organic light emitting device of a reverse structure (inverted type) in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0441] In the organic light-emitting device of the present invention, the organic layer may include an electron blocking layer, and the electron blocking layer may be made of materials known in the technical field.

[0442] For example, the organic light emitting device may have a stacked structure as shown below, but is not limited thereto.

[0443] (1) Anode / hole transport layer / light-emitting layer / cathode

[0444] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0445] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0446] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0447] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0448] (6) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0449] (7) Anode / hole injection layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0450] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0451] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0452] (10) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode

[0453] (11) Anode / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0454] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / cathode

[0455] (13) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0456] (14) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0457] (15) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0458] (16) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0459] (17) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0460] The structure of the organic light-emitting device of the present specification may have the following Figure 1 and Figure 2 The structure shown is not limited thereto.

[0461] Figure 1 The structure of the organic light-emitting device is exemplified in which a substrate 1, an anode 2, a light-emitting layer 6, and a cathode 9 are sequentially stacked. In the structure described above, the compound may be contained in the light-emitting layer 6.

[0462] Figure 2 The structure of an organic light-emitting device is illustrated, which is sequentially stacked with 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 injection and transport layer 8, and a cathode 9. In the structure described above, the above 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 injection and transport layer 8.

[0463] In one embodiment of the present 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 disposed in physical contact with each other.

[0464] In one embodiment of the present 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 disposed in physical contact with each other.

[0465] The organic light-emitting device of the present specification can be manufactured using materials and methods known in the technical field, except that at least one layer of the organic material layer contains the above compound, that is, the compound represented by the above Chemical Formula 1.

[0466] When the organic light-emitting device includes a plurality of organic layers, the organic layers may be formed of the same substance or different substances.

[0467] For example, the organic light-emitting device according to the present specification can be manufactured as follows: using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, a metal or a conductive metal oxide or an alloy thereof is evaporated on a substrate to form an anode, and then an organic 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 is formed on the anode, and then a substance that can be used as a cathode is evaporated on the organic layer. In addition to this method, an organic light-emitting device can also be manufactured by sequentially evaporating a cathode substance, an organic layer, and an anode substance on a substrate.

[0468] The organic layer may further include one or more of a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.

[0469] The organic layer may be a multilayer structure including a hole injection layer, a hole transport layer, an electron injection and transport layer, an electron blocking layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, etc., but is not limited thereto and may also be a single layer structure. In addition, the organic layer may be made of various polymer materials and by a solvent process other than evaporation, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer to form a smaller number of layers.

[0470] The anode is an electrode for injecting holes. As the anode material, in order to enable holes to be smoothly injected into the organic layer, a material with a large work function is preferably used. Specific examples of anode materials that can be used in the present 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, Indium Tin Oxide), and indium zinc oxide (IZO, Indium Zinc Oxide); combinations of metals and oxides such as ZnO:Al or SnO2: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.

[0471] The cathode is an electrode for injecting electrons. In order to facilitate the injection of electrons into the organic layer, the cathode material is preferably a material with a small work function. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloys thereof; multilayer structure materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0472] The hole injection layer is a layer that plays a role in making the injection of holes from the anode to the light-emitting layer smooth. The hole injection material is a material that can well receive holes from the anode at a low voltage. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode material and the HOMO of the surrounding organic layer. As specific examples of hole injection materials, there are metal porphyrines, oligothiophenes, arylamine organics, hexanitrile hexaazatriphenylene organics, quinacridone organics, perylene organics, anthraquinones, polyaniline and polythiophene conductive polymers, but are not limited to this. The thickness of the hole injection layer can be 1 to 150nm. When the thickness of the hole injection layer is more than 1nm, it has the advantage of preventing the hole injection characteristics from being reduced. When it is less than 150nm, it has the advantage of preventing the driving voltage from rising when the thickness of the hole injection layer is too thick to improve the migration of holes.

[0473] The hole transport layer can play a role in smoothing the transport of holes. The hole transport material is a material that can receive holes from the anode or the hole injection layer and transfer them to the light-emitting layer, and a material with a large hole mobility is suitable. As specific examples, there are arylamine organic substances, conductive polymers, and block copolymers with both conjugated parts and non-conjugated parts, but are not limited to these.

[0474] A hole buffer layer may be further disposed between the hole injection layer and the hole transport layer, and may include hole injection or transport materials known in the art.

[0475] An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may be made of the above-mentioned compounds or materials known in the art.

[0476] The above-mentioned light-emitting layer can emit red, green or blue light, and can be formed of a phosphorescent material or a fluorescent material. The above-mentioned light-emitting material is a material that can receive holes and electrons from the hole transport layer and the electron transport layer respectively and combine them to emit light in the visible light region, and is preferably a material with high quantum efficiency for fluorescence or phosphorescence. As specific examples, there are 8-hydroxy-quinoline aluminum complexes (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; benzo azole, benzothiazole and benzimidazole compounds; poly(p-phenylene vinylene) (PPV) polymers; spiro compounds; polyfluorene, rubrene, etc., but are not limited to these.

[0477] The main material of the light-emitting layer includes aromatic fused ring derivatives or heterocyclic compounds. Specifically, aromatic fused ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, etc. Pyrimidine derivatives, etc., but are not limited to these.

[0478] When the light-emitting layer emits red light, as a light-emitting dopant, phosphorescent substances such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium, bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonateiridium, bis(1-phenylquinoline)acetylacetonateiridium), PQIr(tris(1-phenylquinoline)iridium, tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum), or fluorescent substances such as Alq3(tris(8-hydroxyquinolino)aluminum), but are not limited to these. When the light-emitting layer emits green light, as a light-emitting dopant, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium, face tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3(tris(8-hydroxyquinoline)aluminum) can be used, but it is not limited to these. When the light-emitting layer emits blue light, as a light-emitting dopant, phosphorescent materials such as (4,6-F2ppy)2Irpic or fluorescent materials such as spiro-DPVBi, spiro-6P, distyrylbenzene (DSB), distyrylarylene (DSA), PFO-based polymers, and PPV-based polymers can be used, but it is not limited to these.

[0479] A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and a material known in the technical field may be used.

[0480] The above-mentioned electron transport layer can play a role in smoothing the transmission of electrons. The electron transport material is a material that can receive electrons well from the cathode and transfer them to the light-emitting layer, and is suitable for materials with high electron mobility. As specific examples, there are the above-mentioned compounds or Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, hydroxyflavone-metal complexes, etc., but are not limited to this. The thickness of the electron transport layer can be 1 to 50nm. When the thickness of the electron transport layer is more than 1nm, it has the advantage of preventing the electron transport characteristics from being reduced. When it is less than 50nm, it has the advantage of preventing the driving voltage from rising in order to improve the migration of electrons when the thickness of the electron transport layer is too thick.

[0481] The electron injection layer can play a role in facilitating the injection of electrons. As the electron injection material, the following compounds are preferred: compounds that have the ability to transport electrons, have the effect of injecting electrons from the cathode, have an excellent electron injection effect on the light-emitting layer or the light-emitting material, prevent the excitons generated in the light-emitting layer from migrating to the hole injection layer, and have excellent thin film forming ability. Specifically, there are fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, Azoles, Examples include, but are not limited to, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylene methane, anthrone, and derivatives thereof, metal coordination compounds, and nitrogen-containing five-membered ring derivatives.

[0482] Examples of the metal coordination compounds include, but are not limited to, 8-hydroxyquinoline lithium, 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.

[0483] The hole blocking layer is a layer that prevents holes from reaching the cathode and can usually be formed using the same conditions as the hole injection layer. Examples of the compound include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0484] The organic light emitting device according to the present invention may be a top emission type, a bottom emission type, or a bi-directional emission type according to the materials used.

[0485] The organic light-emitting device according to the present specification can be included in various electronic devices for use. For example, the electronic device can be a display panel, a touch panel, a solar module, a lighting device, etc., but is not limited thereto.

[0486] Below, in order to specifically describe this specification, an embodiment will be cited to describe in detail. However, the embodiments according to this specification can be deformed into various different forms, and it is not interpreted that the scope of this application is limited to the embodiments described in detail below. The embodiments of this application are provided to more completely describe this specification to those skilled in the art.

[0487] <Synthesis example>

[0488] Synthesis Example 1. Synthesis of Compound 1

[0489]

[0490] Toluene (200 ml) was added to 9-(3″-chloro-[1,1′:2′,1″-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol), N-phenyl-[1,1′:4′,1″-terphenyl]-4-amine (15.25 g, 47.45 mmol), and sodium tert-butoxide (6.26 g, 65.13 mmol), and the mixture was heated and stirred for 10 minutes. Bis(tri-tert-butylphosphine)palladium (0.12 g, 0.23 mmol) dissolved in toluene (20 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was completed and filtered, the layers were separated with toluene and water. After removing the solvent, the mixture was recrystallized with ethyl acetate to obtain the above compound 1 (26.5 g, yield 79.68%). (MS[M+H] + =715)

[0491] Synthesis Example 2. Synthesis of Compound 2

[0492]

[0493] Using 9-(3″-chloro-[1,1′:2′,1″-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and di([1,1′-biphenyl]-4-yl)amine (15.25 g, 47.45 mmol), the above-mentioned compound 2 (27.00 g, yield 81.18%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =715)

[0494] Synthesis Example 3. Synthesis of Compound 3

[0495]

[0496] Using 9-(3″-chloro-[1,1′:2′,1″-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-2-amine (15.25 g, 47.45 mmol), the above-mentioned compound 3 (26.00 g, yield 78.18%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =715)

[0497] Synthesis Example 4. Synthesis of Compound 4

[0498]

[0499] Using 9-(3″-chloro-[1,1′:2′,1″-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-([1,1′-biphenyl]-2-yl)-[1,1′:4′,1″-terphenyl]-4-amine (18.86 g, 47.45 mmol), the above-mentioned compound 4 (29.00 g, yield 78.81%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =791)

[0500] Synthesis Example 5. Synthesis of Compound 5

[0501]

[0502] Using 9-(3″-chloro-[1,1′:2′,1″-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-(4-(naphthalen-1-yl)phenyl)-[1,1′-biphenyl]-4-amine (17.63 g, 47.45 mmol), the above-mentioned compound 5 (28.00 g, yield 78.68%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =765)

[0503] Synthesis Example 6. Synthesis of Compound 6

[0504]

[0505] Using 9-(3"-chloro-[1,1':2',1"-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-(4-(naphthalen-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol), the above-mentioned compound 6 (28.00 g, yield 78.68%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =765)

[0506] Synthesis Example 7. Synthesis of Compound 7

[0507]

[0508] Using 9-(3″-chloro-[1,1′:2′,1″-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and 4-(phenanthrene-9-yl)-N-phenylaniline (16.39 g, 47.45 mmol), the above-mentioned compound 7 (27.00 g, yield 78.55%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =739)

[0509] Synthesis Example 8. Synthesis of Compound 8

[0510]

[0511] Using 9-(3″-chloro-[1,1′:2′,1″-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-([1,1′-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (21.90 g, 47.45 mmol), the above-mentioned compound 8 (27.00 g, yield 76.88%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =755)

[0512] Synthesis Example 9. Synthesis of Compound 9

[0513]

[0514] Using 9-(3″-chloro-[1,1′:2′,1″-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-([1,1′-biphenyl]-4-yl)dibenzo[b,d]furan-4-amine (15.92 g, 47.45 mmol), the above-mentioned compound 9 (26.50 g, yield 78.15%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =729)

[0515] Synthesis Example 10. Synthesis of Compound 10

[0516]

[0517] Using 9-(3″-chloro-[1,1′:2′,1″-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and bis(4-(tert-butyl)phenyl)amine (13.35 g, 47.45 mmol), the above-mentioned compound 10 (24.00 g, yield 76.44%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =675)

[0518] Synthesis Example 11. Synthesis of Compound 11

[0519]

[0520] Using 9-(4″-chloro-[1,1′:2′,1″-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-phenyl-[1,1′:4′,1″-terphenyl]-4-amine (15.25 g, 47.45 mmol), the above-mentioned compound 11 (26.00 g, yield 78.18%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =715)

[0521] Synthesis Example 12. Synthesis of Compound 12

[0522]

[0523] Using 9-(4"-chloro-[1,1':2',1"-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and di([1,1'-biphenyl]-4-yl)amine (15.25 g, 47.45 mmol), the above-mentioned compound 12 (26.50 g, yield 79.68%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =715)

[0524] Synthesis Example 13. Synthesis of Compound 13

[0525]

[0526] Using 9-(4"-chloro-[1,1':2',1"-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine (15.25 g, 47.45 mmol), the above-mentioned compound 13 (26.00 g, yield 78.18%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =715)

[0527] Synthesis Example 14. Synthesis of Compound 14

[0528]

[0529] Using 9-(4″-chloro-[1,1′:2′,1″-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-([1,1′-biphenyl]-2-yl)-[1,1′:4′,1″-terphenyl]-4-amine (18.86 g, 47.45 mmol), the above-mentioned compound 14 (29.00 g, yield 78.81%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =791)

[0530] Synthesis Example 15. Synthesis of Compound 15

[0531]

[0532] Using 9-(4"-chloro-[1,1':2',1"-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-(4-(naphthalen-1-yl)phenyl)-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol), the above-mentioned compound 15 (28.50 g, yield 80.09%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =765)

[0533] Synthesis Example 16. Synthesis of Compound 16

[0534]

[0535] Using 9-(4"-chloro-[1,1':2',1"-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-(4-(naphthalen-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol), the above-mentioned compound 16 (28.00 g, yield 78.68%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H]+ =765)

[0536] Synthesis Example 17. Synthesis of Compound 17

[0537]

[0538] Using 9-(4"-chloro-[1,1':2',1"-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and 4-(phenanthrene-9-yl)-N-phenylaniline (16.39 g, 47.45 mmol), the above-mentioned compound 17 (27.00 g, yield 78.55%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =739)

[0539] Synthesis Example 18. Synthesis of Compound 18

[0540]

[0541] Using 9-(4"-chloro-[1,1':2',1"-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (21.90 g, 47.45 mmol), the above-mentioned compound 18 (27.50 g, yield 78.30%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =755)

[0542] Synthesis Example 19. Synthesis of Compound 19

[0543]

[0544] Using 9-(4"-chloro-[1,1':2',1"-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-4-amine (15.92 g, 47.45 mmol), the above-mentioned compound 19 (26.50 g, yield 78.15%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =729)

[0545] Synthesis Example 20. Synthesis of Compound 20

[0546]

[0547] Using 9-(4"-chloro-[1,1':2',1"-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and bis(4-(tert-butyl)phenyl)amine (13.35 g, 47.45 mmol), the above-mentioned compound 20 (24.00 g, yield 76.44%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =675)

[0548] Synthesis Example 21. Synthesis of Compound 21

[0549]

[0550] Using 9-(4"-chloro-[1,1':2',1"-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and diphenylamine (8.03 g, 47.45 mmol), the above-mentioned compound 21 (19.00 g, yield 72.58%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =563)

[0551] Synthesis Example 22. Synthesis of Compound 22

[0552]

[0553] Using 9-(2″-chloro-[1,1′:2′,1″-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-phenyl-[1,1′:4′,1″-terphenyl]-4-amine (15.25 g, 47.45 mmol), the above-mentioned compound 22 (26.00 g, yield 78.18%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =715)

[0554] Synthesis Example 23. Synthesis of Compound 23

[0555]

[0556] Using 9-(2"-chloro-[1,1':2',1"-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and di([1,1'-biphenyl]-4-yl)amine (15.25 g, 47.45 mmol), the above-mentioned compound 23 (26.50 g, yield 79.68%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =715)

[0557] Synthesis Example 24. Synthesis of Compound 24

[0558]

[0559] Using 9-(2"-chloro-[1,1':2',1"-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-2-amine (15.25 g, 47.45 mmol), the above-mentioned compound 24 (26.00 g, yield 78.18%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =715)

[0560] Synthesis Example 25. Synthesis of Compound 25

[0561]

[0562] Using 9-(2″-chloro-[1,1′:2′,1″-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-([1,1′-biphenyl]-2-yl)-[1,1′:4′,1″-terphenyl]-4-amine (18.86 g, 47.45 mmol), the above-mentioned compound 25 (29.50 g, yield 80.17%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =791)

[0563] Synthesis Example 26. Synthesis of Compound 26

[0564]

[0565] Using 9-(2"-chloro-[1,1':2',1"-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-(4-(naphthalen-1-yl)phenyl)-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol), the above-mentioned compound 26 (28.50 g, yield 80.09%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =765)

[0566] Synthesis Example 27. Synthesis of Compound 27

[0567]

[0568] Using 9-(2"-chloro-[1,1':2',1"-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-(4-(naphthalen-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (17.63 g, 47.45 mmol), the above-mentioned compound 27 (28.00 g, yield 78.68%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =765)

[0569] Synthesis Example 28. Synthesis of Compound 28

[0570]

[0571] Using 9-(2"-chloro-[1,1':2',1"-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and 4-(phenanthrene-9-yl)-N-phenylaniline (16.39 g, 47.45 mmol), the above-mentioned compound 28 (27.00 g, yield 78.55%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS [M+H] + =739)

[0572] Synthesis Example 29. Synthesis of Compound 29

[0573]

[0574] Using 9-(2"-chloro-[1,1':2',1"-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine (21.90 g, 47.45 mmol), the above-mentioned compound 29 (27.00 g, yield 76.88%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =755)

[0575] Synthesis Example 30. Synthesis of Compound 30

[0576]

[0577] Using 9-(2"-chloro-[1,1':2',1"-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and N-([1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-4-amine (15.92 g, 47.45 mmol), the above-mentioned compound 30 (26.50 g, yield 78.15%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =729)

[0578] Synthesis Example 31. Synthesis of Compound 31

[0579]

[0580] Using 9-(2"-chloro-[1,1':2',1"-terphenyl]-3-yl)-9H-carbazole (20.00 g, 46.52 mmol) and bis(4-(tert-butyl)phenyl)amine (13.35 g, 47.45 mmol), the above-mentioned compound 31 (24.50 g, yield 78.03%) was obtained by the same method as the above-mentioned Synthesis Example 1. (MS[M+H] + =675)

[0581] Synthesis Example 32. Synthesis of Compound 32

[0582]

[0583] The compound 2 (20.0 g, 27.98 mmol) obtained in the above-mentioned synthesis example 2 was added to benzene-d6 (200 ml), and after it was completely dissolved, trifluoromethanesulfonic acid (1.3 ml, 13.98 mmol) was added and stirred for 25 minutes. After the reaction was completed, dichloromethane was added and the layers were separated to obtain an organic layer. After drying with anhydrous magnesium sulfate (MgSO4), it was filtered. The filtrate was concentrated under reduced pressure and recrystallized with ethyl acetate to obtain the above-mentioned compound 32 (16.0 g, 77.90%). (MS[M+H] + =734)

[0584] Synthesis Example 33. Synthesis of Compound 33

[0585]

[0586] Compound 12 (20.0 g, 27.98 mmol) obtained in Synthesis Example 12 was used to obtain Compound 33 (16.00 g, yield 77.90%) by the same method as Synthesis Example 32. (MS [M+H] + =734)

[0587] Synthesis Example 34. Synthesis of Compound 34

[0588]

[0589] Compound 23 (20.0 g, 27.98 mmol) obtained in Synthesis Example 23 was used to obtain Compound 34 (15.50 g, yield 75.47%) by the same method as Synthesis Example 32. (MS [M+H] + =734)

[0590] <Experimental Examples and Comparative Experimental Examples>

[0591] Experimental Example 1-1

[0592] ITO (indium tin oxide) The glass substrate coated with a film of a thickness of 10000 mm was placed in distilled water dissolved with a detergent and washed with ultrasonic waves. At this time, the detergent used a product of Fischer Co., and the distilled water used distilled water filtered twice by a filter manufactured by Millipore Co. After ITO was washed for 30 minutes, ultrasonic washing was repeated twice with distilled water for 10 minutes. After the distilled water washing was completed, ultrasonic washing was carried out with a solvent of isopropanol, acetone, and methanol and dried, and then transported to a plasma cleaning machine. In addition, after the above-mentioned substrate was cleaned for 5 minutes using oxygen plasma, the substrate was transported to a vacuum evaporator.

[0593] On the ITO transparent electrode prepared in this way, a compound represented by the following chemical formula HAT was applied as A hole injection layer was formed by thermal vacuum deposition of a thickness of 1000 nm. On the hole injection layer, a compound represented by the following chemical formula HT1 was deposited as a hole transport layer. After vacuum deposition with a thickness of , as an electron blocking layer, the compound 1 prepared in the above-mentioned Synthesis Example 1 was Next, as a light-emitting layer, a compound represented by the following chemical formula BH and a compound represented by the following chemical formula BD were prepared at a weight ratio of 25:1 and Next, as a hole blocking layer, a compound represented by the following chemical formula HB1 was deposited in the form of Next, as a layer for simultaneously performing electron injection and electron transport, a compound represented by the following chemical formula ET1 and a compound represented by the following Liq were added at a weight ratio of 1:1 and On the electron transport and electron injection layers, lithium fluoride (LiF) is deposited in the form of The thickness of the aluminum A cathode is formed by evaporation with a thickness of , thereby manufacturing an organic light-emitting device.

[0594]

[0595] Experimental Examples 1-2 to 1-34 and Comparative Experimental Examples 1-1 to 1-2

[0596] In the above Experimental Example 1-1, the organic light-emitting devices of Experimental Examples 1-2 to 1-34 and Comparative Experimental Examples 1-1 to 1-2 were prepared by the same method as the above Experimental Example 1-1, except that the compounds listed in the following Table 1 were used instead of Compound 1. The organic light-emitting devices prepared in the Experimental Examples and Comparative Experimental Examples were subjected to a 10 mA / cm 2 When the current was 1.5 %, the voltage, efficiency, color coordinates and life were measured, and the results are shown in the following Table 1. On the other hand, T95 represents the time required for the luminance to decrease from the initial luminance (6000 nits) to 95%.

[0597]

Table 1

[0598]

[0599]

[0600] As shown in Table 1 above, it is confirmed that compounds 1 to 34 are compounds in which the terphenyl linking group (meta-ortho direction) between carbazole and amine is substituted or unsubstituted by deuterium, and compared with compounds EB1 and EB2 in which the terphenyl linking group (meta-ortho direction) between carbazole and amine is substituted by an aryl or heteroaryl group, they have HOMO and LUMO energy levels that can control the potential barrier with the adjacent organic layer. As such compounds, they have excellent electron blocking ability, and organic light-emitting devices using them as electron blocking layers show significant effects in terms of driving voltage, efficiency and life.

[0601] In addition, compared with compound 21 in which the terphenyl linking group is linked to the amine at the para position and all the substituents of the amine are phenyl groups, compounds 1 to 20 and compounds 22 to 34, which are linked to the amine at the ortho or meta position, have suitable HOMO and LUMO energy levels and show excellent electron blocking ability.

[0602] Experimental Examples 2-1 to 2-34 and Comparative Experimental Examples 1-1, 2-1 to 2-3

[0603] In the above Experimental Example 1-1, the compound represented by the above chemical formula EB1 was used instead of the compound 1 as the electron blocking layer, and the compound described in the following Table 2 was used instead of the compound represented by the above chemical formula HT1 as the hole transport layer. In addition, the organic light-emitting devices of Experimental Examples 2-1 to 2-34 and Comparative Experimental Examples 2-1 to 2-3 were prepared by the same method as the above Experimental Example 1-1. The organic light-emitting devices prepared in the Experimental Examples and Comparative Experimental Examples were subjected to a 10 mA / cm 2When the current was 1.5 %, the voltage, efficiency, color coordinates and life were measured, and the results are shown in the following Table 2. On the other hand, T95 represents the time required for the luminance to decrease from the initial luminance (6000 nits) to 95%.

[0604]

Table 2

[0605]

[0606]

[0607] As shown in Table 2 above, it was confirmed that compounds 1 to 34 are compounds in which the terphenyl linking group (meta-ortho direction) between the carbazole and the amine group is substituted by deuterium or unsubstituted, and compared with compounds HT2 to HT4 in which the terphenyl linking group (meta-ortho direction) between the carbazole and the amine is substituted by an aromatic or heteroaromatic group, they have excellent hole transport capabilities, and organic light-emitting devices using them as hole transport layers show significant effects in terms of driving voltage, efficiency and life.

[0608] In addition, compared with compound 21 in which the terphenyl linking group is linked to the amine at the para position and all the substituents of the amine are phenyl groups, compounds 1 to 20 and compounds 22 to 34, which are linked to the amine at the ortho or meta position, have suitable HOMO and LUMO energy levels, showing excellent hole transport ability.

Claims

1. A compound represented by the following chemical formula 1: [Chemical formula 1] In the chemical formula 1, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted cycloalkyl group, L1 to L3 are the same as or different from each other, and are each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group, R1 and R2 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a nitrile group, a substituted or unsubstituted silyl group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group, R3 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a halogen group, a substituted or unsubstituted silyl group, a substituted or unsubstituted arylalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group, a substituted or unsubstituted arylalkenyl group, or a substituted or unsubstituted heterocyclic group containing O or S, a to e are each an integer of 1 to 4. When a to e is 2 or more, two or more R1 to R5 are the same or different from each other. p to r are each an integer of 1 to 4, and when p to r is 2 or more, two or more L1 to L3 are each the same as or different from each other.

2. The compound according to claim 1, wherein The chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-3: [Chemical formula 1-1] [Chemical formula 1-2] [Chemical formula 1-3] In the chemical formulas 1-1 to 1-3, Definitions of Ar1, Ar2, L1 to L3, R1 to R5, a to e, and p to r are the same as those in Chemical Formula 1.

3. The compound according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

4. The compound according to claim 1, wherein Ar1 and Ar2 are the same as or different from each other, and are each independently substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted anthracenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted dibenzofuranyl, or substituted or unsubstituted adamantyl.

5. The compound according to claim 1, wherein The chemical formula 1 is represented by any one of the following chemical formulas 2-1 to 2-6: [Chemical formula 2-1] [Chemical formula 2-2] [Chemical formula 2-3] [Chemical formula 2-4] [Chemical formula 2-5] [Chemical formula 2-6] In the chemical formulas 2-1 to 2-6, The definitions of Ar1, Ar2, L1 to L3, R1 to R5, a to e and p to r are the same as those in the chemical formula 1. D is deuterium, f1 to f3 are 0 to 4, respectively.

6. The compound according to claim 1, wherein L1 to L3 are directly bonded or substituted or unsubstituted arylene groups having 6 to 30 carbon atoms.

7. The compound according to claim 1, wherein The chemical formula 1 is represented by the following chemical formula 3: [Chemical formula 3] In the chemical formula 3, Ar1, Ar2, R1 to R5, and a to e are defined the same as those in the chemical formula 1. D is deuterium, x1 to x3 are each 0 to 4, s1 to s3 are 0 or 1, respectively.

8. The compound according to claim 1, wherein The chemical formula 1 is represented by any one of the following chemical formulas 3-1 to 3-3: [Chemical formula 3-1] [Chemical formula 3-2] [Chemical formula 3-3] In the chemical formulas 3-1 to 3-3, Ar1, Ar2, R1 to R5, and a to e are defined the same as those in the chemical formula 1. D is deuterium, x1 to x3 are 0 to 4, respectively, s1 to s3 are 0 or 1, respectively.

9. The compound according to claim 1, wherein R1 to R5 are the same as or different from each other, and are each independently hydrogen or deuterium.

10. The compound according to claim 1, wherein The chemical formula 1 is represented by any one of the following chemical formulas 4-1 to 4-4: In the chemical formulas 4-1 to 4-4, Ar1, Ar2, L1, L3, R1 to R5, a to e, p and r are defined as in the chemical formula 1, D is deuterium, x4 and x5 are 0 to 4 respectively, y is 0 to 5, z is 0 to 7.

11. The compound according to claim 1, wherein The chemical formula 1 is represented by any one of the following compounds:

12. The compound according to claim 1, wherein The chemical formula 1 is represented by any one of the following compounds: In the compound, D is deuterium, n is an integer of 1 or more.

13. An organic light emitting device, wherein: include: An anode, a cathode, and one or more organic layers provided between the anode and the cathode, wherein one or more of the organic layers comprises the compound according to any one of claims 1 to 12.

14. The organic light emitting device according to claim 13, wherein: The organic light emitting device comprises a light emitting layer, An organic layer including the compound is located between the anode and the light emitting layer.

15. The organic light emitting device according to claim 13, wherein: The organic 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 contains the compound.

16. The organic light emitting device according to claim 13, wherein: The organic layer includes an electron blocking layer, and the electron blocking layer includes the compound.

17. The organic light emitting device according to claim 13, wherein: The organic layer further includes one or more of a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron injection and transport layer.

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