Compounds and organic light emitting devices comprising the same

Abstract

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

Description

Technical Field

[0001] This application claims priority to Korean Patent Application No. 10-2022-0045344, filed with the Korean Patent Office on April 12, 2022, the entire contents of which are disclosed in the document and are incorporated herein by reference.

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

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

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

[0005] Existing technical documents

[0006] Patent documents

[0007] (Patent Document 1) KR 10-2014-0076888 Summary of the Invention

[0008] Technical issues

[0009] This specification provides compounds and organic light-emitting devices containing them.

[0010] Solution to the problem

[0011] One embodiment of this specification provides a compound represented by the following chemical formula 1.

[0012] [Chemical Formula 1]

[0013]

[0014] In the above chemical formula 1,

[0015] R1 and R2 may be the same as or different from each other, and each may independently be hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.

[0016] At least one of R1 and R2 is an alkyl group having 1 to 3 carbon atoms.

[0017] At least one of R2 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0018] Ar1 and Ar2 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0019] L1 to L3 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group.

[0020] When a is an integer from 1 to 8, and a is 2 or higher, R1 is either the same or different from each other.

[0021] When b is an integer from 1 to 3, and b is 2 or more, R2 is either the same or different from each other.

[0022] In addition, one embodiment of this specification provides an organic light-emitting device, which includes: an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers contain a compound represented by the above chemical formula 1.

[0023] Invention Effects

[0024] The compounds described in this specification can be used as materials for the organic layer of organic light-emitting devices. The compounds according to at least one embodiment of this specification can achieve improved efficiency, lower driving voltage, and / or improved lifetime characteristics in organic light-emitting devices. In particular, the compounds described in this specification can be used as materials for hole injection, hole transport, hole injection and hole transport, electron blocking, light emission, hole blocking, electron transport, or electron injection. Furthermore, compared to existing organic light-emitting devices, they exhibit the effects of lower driving voltage, higher efficiency, and / or longer lifetime. Attached Figure Description

[0025] Figure 1 The illustration shows an example of an organic light-emitting device in which a substrate 1, an anode 2, an organic layer 10, and a cathode 9 are stacked in sequence.

[0026] Figure 2 The illustration shows an example of an organic light-emitting device in which a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 9 are stacked in sequence.

[0027] [Symbol Explanation]

[0028] 1: Substrate

[0029] 2: Anode

[0030] 3: Hole injection layer

[0031] 4: Hole transport layer

[0032] 5: Electron blocking layer

[0033] 6: Emissive layer

[0034] 7: Cavity blocking layer

[0035] 8: Electron Injection and Transport Layer

[0036] 9: Cathode

[0037] 10: Organic layer Detailed Implementation

[0038] The following is a more detailed description of this instruction manual.

[0039] In this specification, when a part is indicated to "include" a certain component, unless otherwise stated, it means that other components may be included, rather than excluded.

[0040] In this specification, when it is stated that a component is "on" another component, it includes not only the case where one component is connected to another component, but also the case where there are other components between the two components.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

[0059] In this specification, the substituted aryl group may also include forms in which an aliphatic ring is fused to the aryl group. For example, the tetrahydronaphthyl group in the following structure is included in the substituted aryl group. In the following structure, one of the carbon atoms of the benzene ring may be attached to other positions.

[0060]

[0061] In this specification, the aryl group in the aryl group can be described in the above description of the aryl group.

[0062] In this specification, the alkyl groups in the above-mentioned alkylthio and alkylsulfonyl groups are subject to the above description of alkyl groups.

[0063] In this specification, the aryl groups in the above-mentioned aryl thiol and aryl sulfonyl groups are subject to the above description of aryl groups.

[0064] In this specification, a heterocyclic group is a cyclic group containing one or more of N, O, P, S, Si, and Se as heteroatoms. The number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the heterocyclic group has 2 to 30 carbon atoms. According to another embodiment, the heterocyclic group has 2 to 20 carbon atoms. Examples of heterocyclic groups include pyridyl, pyrroloyl, pyrimidinyl, quinolinyl, pyridazinyl, furanyl, thiopheneyl, imidazoyl, pyrazolyl, dibenzofuranyl, dibenzothiopheneyl, carbazoleyl, benzocarbazoleyl, naphthobenzofuranyl, benzonaphthothiopheneyl, indenzocarbazoleyl, triazinyl, etc., but are not limited to these.

[0065] In this specification, heteroaryl refers to aromatic compounds; otherwise, the above description of heterocyclic groups applies.

[0066] In this specification, the term arylene can be used to describe aryl groups except that it is divalent.

[0067] In this specification, the term "divalent heterocyclic" can be used in the same way as the above description of heterocyclic groups, except that it is divalent.

[0068] In this specification, "ring" refers to a hydrocarbon ring or heterocycle in the context of a substituted or unsubstituted ring formed by the combination of adjacent groups with each other.

[0069] The aforementioned hydrocarbon ring can be aromatic, aliphatic, or a fused ring of aromatic and aliphatic compounds, and can be selected from the examples of the aforementioned cycloalkyl or aryl groups.

[0070] In this specification, the term "forming a ring by bonding with adjacent groups" means forming a substituted or unsubstituted aliphatic hydrocarbon ring, a substituted or unsubstituted aromatic hydrocarbon ring, a substituted or unsubstituted aliphatic heterocycle, a substituted or unsubstituted aromatic heterocycle, or a fused ring thereof by bonding with adjacent groups. The aforementioned hydrocarbon ring refers to a ring composed only of carbon and hydrogen atoms. The aforementioned heterocycle refers to a ring containing one or more elements selected from N, O, P, S, Si, and Se. In this specification, the aforementioned aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocycle, and aromatic heterocycle can be monocyclic or polycyclic.

[0071] In this specification, aliphatic hydrocarbon rings refer to non-aromatic rings composed only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene, but are not limited to these.

[0072] In this specification, aromatic hydrocarbon rings refer to aromatic rings composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenatene, pyrene, tetraphenylene, phenazine, pentaphenylene, fluorene, indene, acenaphthene, benzo[a]fluorene, spirofluorene, etc., but are not limited to these. In this specification, aromatic hydrocarbon rings can be interpreted in the same way as aryl groups.

[0073] In this specification, an aliphatic heterocycle refers to an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include oxirane, tetrahydrofuran, and 1,4-dioxane. Alkane (1,4-dioxane), pyrrolidine, piperidine, morpholine, oxacycloheptane, azirrocyclooctane, thiocyclooctane, etc., but not limited to these.

[0074] In this specification, an aromatic heterocycle refers to an aromatic ring containing one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, etc. azole, isotonic azole, thiazole, isothiazole, triazole Diazole, thiadiazole, dithiazolium, tetrazolium, pyran, thiaran, pyridazine Azine, thiazide, diazine Alkenes, triazines, tetraazines, isoquinoline, quinoline, benzoquinone, quinazoline, quinoxaline, naphthidine, acridine, phenanthridine, diazanine, triazine, indole, indolezine, benzothiazole, benzo[] azole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, imidazopyridine, phenazine It includes aziridines, indobenzocarbazole, indobenzocarbazole, etc., but is not limited to these.

[0075] Preferred embodiments of the present invention will now be described in detail. However, the embodiments of the present invention can be modified in various ways, and the scope of the present invention is not limited to the embodiments described below.

[0076] According to the present invention, the compound represented by chemical formula 1 can modulate the HOMO and LUMO energy levels of the compound by attaching an amino group to tetrahydronaphthalene, thereby modulating the energy barrier between the compound and the organic layer.

[0077] In particular, the compounds represented by chemical formula 1 according to the present invention can adjust the hole migration characteristics of the compounds by having alkyl substituents with 1 to 3 carbon atoms on tetrahydronaphthalene, or having alkyl or aryl substituents on the benzene ring portion of tetrahydronaphthalene, thereby adjusting the hole and electron balance of the device.

[0078] Therefore, when the compound represented by the above chemical formula 1 is applied to organic light-emitting devices, organic light-emitting devices with high efficiency, low voltage and / or long lifetime characteristics can be obtained.

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

[0080] [Chemical Formula 1]

[0081]

[0082] In the above chemical formula 1,

[0083] R1 and R2 may be the same as or different from each other, and each may independently be hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.

[0084] At least one of R1 and R2 is an alkyl group having 1 to 3 carbon atoms.

[0085] At least one of R2 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group.

[0086] Ar1 and Ar2 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0087] L1 to L3 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group.

[0088] When a is an integer from 1 to 8, and a is 2 or higher, R1 is either the same or different from each other.

[0089] When b is an integer from 1 to 3, and b is 2 or more, R2 is either the same or different from each other.

[0090] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each is independently hydrogen, deuterium, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl.

[0091] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 60 carbon atoms, or substituted or unsubstituted aryl with 6 to 60 carbon atoms.

[0092] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 30 carbon atoms, or substituted or unsubstituted aryl with 6 to 30 carbon atoms.

[0093] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently is hydrogen, deuterium, substituted or unsubstituted alkyl with 1 to 20 carbon atoms, or substituted or unsubstituted aryl with 6 to 20 carbon atoms.

[0094] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.

[0095] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently is hydrogen, deuterium, an alkyl group having 1 to 60 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 60 carbon atoms substituted or unsubstituted with deuterium.

[0096] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently is hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with deuterium.

[0097] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently is hydrogen, deuterium, an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium.

[0098] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently is hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 12 carbon atoms substituted or unsubstituted with deuterium.

[0099] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently is hydrogen, deuterium, an alkyl group having 1 to 3 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with deuterium.

[0100] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently is hydrogen, deuterium, an alkyl group having 1 to 3 carbon atoms substituted or unsubstituted with deuterium, or an aryl group having 6 to 12 carbon atoms substituted or unsubstituted with deuterium.

[0101] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently is hydrogen, deuterium, an alkyl group having 1 to 3 carbon atoms that is substituted with deuterium or not, or a phenyl group that is substituted with deuterium or not.

[0102] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each is independently hydrogen, deuterium, alkyl or phenyl with 1 to 3 carbon atoms.

[0103] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each independently is hydrogen, deuterium, methyl, ethyl, propyl, isopropyl or phenyl.

[0104] In one embodiment of this specification, R1 and R2 may be the same as or different from each other, and each is independently hydrogen, deuterium, methyl, isopropyl or phenyl.

[0105] In one embodiment of this specification, at least one of R1 and R2 is an alkyl group having 1 to 3 carbon atoms.

[0106] In one embodiment of this specification, at least one of R1 and R2 is methyl, ethyl, or isopropyl.

[0107] In one embodiment of this specification, at least one of R1 and R2 is methyl or isopropyl.

[0108] In one embodiment of this specification, at least one of R1 and R2 is a methyl group.

[0109] In one embodiment of this specification, at least one of R2 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

[0110] In one embodiment of this specification, at least one of R2 is an alkyl group having 1 to 10 carbon atoms, either substituted or unsubstituted, or an aryl group having 6 to 20 carbon atoms, either substituted or unsubstituted.

[0111] In one embodiment of this specification, at least one of R2 is an alkyl group having 1 to 3 carbon atoms, either substituted or unsubstituted, or an aryl group having 6 to 10 carbon atoms, either substituted or unsubstituted.

[0112] In one embodiment of this specification, at least one of R2 is a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms, or a substituted or unsubstituted phenyl group.

[0113] In one embodiment of this specification, at least one of R2 is an alkyl group having 1 to 3 carbon atoms that is either deuterated or unsubstituted, or a phenyl group that is either deuterated or unsubstituted.

[0114] In one embodiment of this specification, at least one of R2 is an alkyl or phenyl group having 1 to 3 carbon atoms.

[0115] In one embodiment of this specification, at least one of R2 is methyl, ethyl, propyl, isopropyl, or phenyl.

[0116] In one embodiment of this specification, at least one of R2 is methyl, isopropyl, or phenyl.

[0117] In one embodiment of this specification, R1 is hydrogen, deuterium, or methyl, and R2 is hydrogen, deuterium, methyl, isopropyl, or phenyl.

[0118] In one embodiment of this specification, R1 is hydrogen or deuterium, and R2 is hydrogen, deuterium, methyl, or isopropyl.

[0119] In one embodiment of this specification, R1 is hydrogen, and R2 is hydrogen, methyl, or isopropyl.

[0120] In one embodiment of this specification, R1 is hydrogen and R2 is hydrogen or methyl.

[0121] In one embodiment of this specification, R1 is hydrogen and R2 is hydrogen or isopropyl.

[0122] In one embodiment of this specification, R1 is hydrogen and R2 is methyl or isopropyl.

[0123] In one embodiment of this specification, R1 is hydrogen and R2 is methyl.

[0124] In one embodiment of this specification, R1 is hydrogen and R2 is isopropyl.

[0125] In one embodiment of this specification, R1 is methyl and R2 is hydrogen, deuterium, methyl, isopropyl or phenyl.

[0126] In one embodiment of this specification, R1 is methyl and R2 is methyl or isopropyl.

[0127] In one embodiment of this specification, R1 is methyl and R2 is phenyl.

[0128] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group, or a substituted or unsubstituted divalent heterocyclic group.

[0129] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group with 6 to 60 carbon atoms, or a divalent heterocyclic group with 2 to 60 carbon atoms, either substituted or unsubstituted.

[0130] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, or a divalent heterocyclic group with 2 to 30 carbon atoms, either substituted or unsubstituted.

[0131] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted aryl group with 6 to 20 carbon atoms, or a divalent heterocyclic group with 2 to 20 carbon atoms, either substituted or unsubstituted.

[0132] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently directly bonded; arylene groups with 6 to 60 carbon atoms, substituted or unsubstituted; or divalent heterocyclic groups containing O, S or N with 2 to 60 carbon atoms, substituted or unsubstituted.

[0133] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently directly bonded; aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted; or divalent heterocyclic groups with 2 to 30 carbon atoms, substituted or unsubstituted, containing O, S, or N. In another embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently directly bonded; aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted with deuterium or alkyl groups with 1 to 30 carbon atoms; or divalent heterocyclic groups with 2 to 30 carbon atoms, substituted or unsubstituted, containing O, S, or N.

[0134] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently directly bonded; arylene group with 6 to 20 substituted or unsubstituted carbon atoms; or divalent heterocyclic group with 2 to 20 substituted or unsubstituted carbon atoms containing O, S or N.

[0135] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently an arylene group with 6 to 30 carbon atoms that is directly bonded, substituted or unsubstituted.

[0136] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently an arylene group with 6 to 30 carbon atoms that is directly bonded or substituted with or unsubstituted with deuterium or alkyl groups.

[0137] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a directly bonded, or a deuterated or alkyl group having 1 to 30 carbon atoms substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0138] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, or a substituted or unsubstituted divalent fluorene.

[0139] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted phenylene or a substituted or unsubstituted biphenylene.

[0140] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a directly bonded, deuterated or alkyl-substituted or unsubstituted phenylene, or a deuterated or alkyl-substituted or unsubstituted biphenylene.

[0141] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a directly bonded, deuterated or alkyl-substituted or unsubstituted phenylene, or a biphenylene substituted or unsubstituted with deuterium or alkyl-substituted or unsubstituted alkylene.

[0142] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a directly bonded, deuterated or alkyl-substituted or unsubstituted phenylene, or a biphenylene substituted or unsubstituted with deuterium or alkyl-substituted or unsubstituted alkylene.

[0143] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a directly bonded, or a deuterated or methyl-substituted or unsubstituted phenylene, or a deuterated or methyl-substituted or unsubstituted biphenylene.

[0144] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a directly bonded, methyl-substituted or unsubstituted phenylene, or methyl-substituted or unsubstituted biphenylene.

[0145] In one embodiment of this specification, L1 to L3 may be the same as or different from each other, and each is independently a directly bonded, methyl-substituted or unsubstituted phenylene or biphenylene.

[0146] In one embodiment of this specification, L1 to L3 are identical to each other and are directly bonded, or substituted or unsubstituted phenylene oxides.

[0147] In one embodiment of this specification, L1 to L3 are identical to each other and are directly bonded, or deuterated or unsubstituted phenylene oxides.

[0148] In one embodiment of this specification, L1 to L3 are identical to each other and are directly bonded or phenylene.

[0149] In one embodiment of this specification, L1 to L3 are identical to each other and are directly bonded.

[0150] In one embodiment of this specification, L1 is a directly bonded, substituted, or unsubstituted phenylene oxide.

[0151] In one embodiment of this specification, L1 is a directly bonded, or substituted or unsubstituted phenylene oxide with deuterium or methyl groups.

[0152] In one embodiment of this specification, L1 is a directly bonded, deuterated, or unsubstituted phenylene oxide.

[0153] In one embodiment of this specification, L1 is a direct bond or a phenylene oxide.

[0154] In one embodiment of this specification, L1 is a direct bond.

[0155] In one embodiment of this specification, L2 and L3 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted phenylene or a substituted or unsubstituted biphenylene.

[0156] In one embodiment of this specification, L2 and L3 may be the same as or different from each other, and each is independently a directly bonded, deuterated or methyl-substituted or unsubstituted phenylene, or a deuterated or methyl-substituted or unsubstituted biphenylene.

[0157] In one embodiment of this specification, L2 and L3 may be the same as or different from each other, and each is independently a directly bonded, substituted or unsubstituted phenylene or a substituted or unsubstituted biphenylene.

[0158] In one embodiment of this specification, L2 and L3 may be the same as or different from each other, and each is independently a directly bonded, deuterated or alkyl-substituted or unsubstituted phenylene, or a deuterated or alkyl-substituted or unsubstituted biphenylene.

[0159] In one embodiment of this specification, L2 and L3 may be the same as or different from each other, and each is independently a directly bonded, methyl-substituted or unsubstituted phenylene or biphenylene.

[0160] In one embodiment of this specification, L2 and L3 are directly bonded.

[0161] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each may be independently a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.

[0162] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each is independently an aryl group with 6 to 60 substituted or unsubstituted carbon atoms, or a heterocyclic group with 2 to 60 substituted or unsubstituted carbon atoms.

[0163] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each is independently an aryl group with 6 to 30 substituted or unsubstituted carbon atoms, or a heterocyclic group with 2 to 30 substituted or unsubstituted carbon atoms.

[0164] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, each being independently an aryl group with 6 to 60 substituted or unsubstituted carbon atoms; or a heterocyclic group containing O, S or N with 2 to 60 substituted or unsubstituted carbon atoms.

[0165] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, each being independently an aryl group with 6 to 30 substituted or unsubstituted carbon atoms; or a heterocyclic group containing O, S or N with 2 to 30 substituted or unsubstituted carbon atoms.

[0166] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, each being independently an aryl group with 6 to 60 carbon atoms substituted or unsubstituted with deuterium, an alkyl group with 1 to 30 carbon atoms, or an aryl group with 6 to 30 carbon atoms; or a heterocyclic group containing O, S, or N with 2 to 60 carbon atoms substituted or unsubstituted with deuterium, an alkyl group with 1 to 30 carbon atoms, or an aryl group with 6 to 30 carbon atoms.

[0167] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, each being independently an aryl group with 6 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group with 1 to 30 carbon atoms, or an aryl group with 6 to 30 carbon atoms; or a heterocyclic group containing O, S, or N with 2 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group with 1 to 30 carbon atoms, or an aryl group with 6 to 30 carbon atoms.

[0168] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, each being independently an aryl group with 6 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group with 1 to 20 carbon atoms, or an aryl group with 6 to 30 carbon atoms; or a heterocyclic group containing O, S, or N with 2 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group with 1 to 20 carbon atoms, or an aryl group with 6 to 30 carbon atoms.

[0169] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, each being independently an aryl group with 6 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group with 1 to 10 carbon atoms, or an aryl group with 6 to 30 carbon atoms; or a heterocyclic group containing O, S, or N with 2 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group with 1 to 10 carbon atoms, or an aryl group with 6 to 30 carbon atoms.

[0170] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, each being independently an aryl group with 6 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group with 1 to 3 carbon atoms, or an aryl group with 6 to 30 carbon atoms; or a heterocyclic group containing O, S, or N with 2 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group with 1 to 3 carbon atoms, or an aryl group with 6 to 30 carbon atoms.

[0171] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, each being independently an aryl group with 6 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group with 1 to 3 carbon atoms, or an aryl group with 6 to 12 carbon atoms; or a heterocyclic group containing O, S, or N with 2 to 30 carbon atoms substituted or unsubstituted with deuterium, an alkyl group with 1 to 3 carbon atoms, or an aryl group with 6 to 12 carbon atoms.

[0172] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted phenanthyl, a substituted or unsubstituted triphenylene, a substituted or unsubstituted tetrahydronaphthyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted dibenzothiopheneyl, or a substituted or unsubstituted carbazoyl.

[0173] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each independently represents a deuterated or unsubstituted phenyl group; a deuterated or unsubstituted biphenyl group; a deuterated or unsubstituted terphenyl group; a deuterated or unsubstituted naphthyl group; a deuterated or unsubstituted phenanthyl group; a deuterated or unsubstituted triphenylene group; a tetrahydronaphthyl group substituted or unsubstituted with one or more substituents selected from deuterium, an alkyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 20 carbon atoms; a deuterated or unsubstituted dibenzofuranyl group; a deuterated or unsubstituted dibenzothiophenyl group; or a deuterated or unsubstituted carbazole group.

[0174] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each independently represents phenyl; biphenyl; terphenyl; naphthyl; phenanthrene; triphenylene; tetrahydronaphthyl substituted or unsubstituted with one or more substituents selected from methyl, isopropyl and phenyl; dibenzofuranyl; dibenzothiopheneyl or carbazoleyl.

[0175] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each independently is phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, tetrahydronaphthyl, dibenzofuranyl, dibenzothiophene, or carbazolyl, substituted or unsubstituted with one or more substituents selected from methyl and isopropyl.

[0176] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each independently represents a deuterated or unsubstituted phenyl group; a deuterated or unsubstituted biphenyl group; a deuterated or unsubstituted terphenyl group; a deuterated or unsubstituted naphthyl group; a deuterated or unsubstituted phenanthryl group; a deuterated or unsubstituted triphenylene group; a tetrahydronaphthyl group substituted or unsubstituted with one or more substituents selected from deuterium, methyl, isopropyl, and phenyl; a deuterated or unsubstituted dibenzofuranyl group; a deuterated or unsubstituted dibenzothiophenyl group; or a deuterated or unsubstituted carbazole group.

[0177] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each independently represents phenyl; biphenyl; terphenyl; naphthyl; phenanthrene; triphenylene; tetrahydronaphthyl substituted or unsubstituted with one or more substituents selected from methyl, isopropyl and phenyl; dibenzofuranyl; dibenzothiopheneyl or carbazoleyl.

[0178] In one embodiment of this specification, Ar1 and Ar2 may be the same as or different from each other, and each independently is phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, tetrahydronaphthyl, dibenzofuranyl, dibenzothiophene, or carbazolyl, substituted or unsubstituted with one or more substituents selected from methyl and isopropyl.

[0179] In one embodiment of this specification, a is an integer from 1 to 8.

[0180] In one embodiment of this specification, a is an integer from 1 to 4.

[0181] In one embodiment of this specification, a is 8.

[0182] In one embodiment of this specification, a is 7.

[0183] In one embodiment of this specification, a is 6.

[0184] In one embodiment of this specification, a is 5.

[0185] In one embodiment of this specification, a is 4.

[0186] In one embodiment of this specification, a is 3.

[0187] In one embodiment of this specification, a is 2.

[0188] In one embodiment of this specification, a is 1.

[0189] In one embodiment of this specification, b is an integer from 1 to 3.

[0190] In one embodiment of this specification, b is 3.

[0191] In one embodiment of this specification, b is 2.

[0192] In one embodiment of this specification, b is 1.

[0193] In one embodiment of this specification, the above-mentioned chemical formula 1 is represented by the following chemical formula 1-1.

[0194] [Chemical Formula 1-1]

[0195]

[0196] In the above chemical formula 1-1,

[0197] The definitions of R1, L1 to L3, Ar1, Ar2, and a are the same as those in Chemical Formula 1 above.

[0198] R3 is a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group.

[0199] In one embodiment of this specification, R3 is an alkyl group having 1 to 60 carbon atoms, either substituted or unsubstituted, or an aryl group having 6 to 60 carbon atoms, either substituted or unsubstituted.

[0200] In one embodiment of this specification, R3 is an alkyl group having 1 to 30 carbon atoms, either substituted or unsubstituted, or an aryl group having 6 to 30 carbon atoms, either substituted or unsubstituted.

[0201] In one embodiment of this specification, R3 is an alkyl group having 1 to 20 carbon atoms, either substituted or unsubstituted, or an aryl group having 6 to 20 carbon atoms, either substituted or unsubstituted.

[0202] In one embodiment of this specification, R3 is an alkyl group having 1 to 10 carbon atoms, either substituted or unsubstituted, or an aryl group having 6 to 12 carbon atoms, either substituted or unsubstituted.

[0203] In one embodiment of this specification, R3 is an alkyl group having 1 to 3 carbon atoms, either substituted or unsubstituted, or an aryl group having 6 to 10 carbon atoms, either substituted or unsubstituted.

[0204] In one embodiment of this specification, R3 is a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms, or a substituted or unsubstituted phenyl group.

[0205] In one embodiment of this specification, R3 is an alkyl group having 1 to 60 carbon atoms that is either deuterated or unsubstituted, or an aryl group having 6 to 60 carbon atoms that is either deuterated or unsubstituted.

[0206] In one embodiment of this specification, R3 is an alkyl group having 1 to 30 carbon atoms that is either deuterated or unsubstituted, or an aryl group having 6 to 30 carbon atoms that is either deuterated or unsubstituted.

[0207] In one embodiment of this specification, R3 is an alkyl group having 1 to 20 carbon atoms that is either deuterated or unsubstituted, or an aryl group having 6 to 20 carbon atoms that is either deuterated or unsubstituted.

[0208] In one embodiment of this specification, R3 is an alkyl group having 1 to 10 carbon atoms that is substituted or unsubstituted with deuterium, or an aryl group having 6 to 12 carbon atoms that is substituted or unsubstituted with deuterium.

[0209] In one embodiment of this specification, R3 is an alkyl group having 1 to 3 carbon atoms that is substituted with deuterium or not, or an aryl group having 6 to 10 carbon atoms that is substituted with deuterium or not.

[0210] In one embodiment of this specification, R3 is an alkyl group having 1 to 3 carbon atoms that is either deuterated or unsubstituted, or a phenyl group that is either deuterated or unsubstituted.

[0211] In one embodiment of this specification, R3 is methyl, ethyl, propyl, isopropyl, or a phenyl group that is either deuterated or unsubstituted.

[0212] In one embodiment of this specification, R3 is methyl, ethyl, propyl, isopropyl, or phenyl.

[0213] In one embodiment of this specification, R3 is methyl, isopropyl, or phenyl.

[0214] In one embodiment of this specification, R3 is methyl or phenyl.

[0215] In one embodiment of this specification, the above chemical formula 1 is represented by any one of the following chemical formulas 2-1 to 2-3.

[0216] [Chemical Formula 2-1]

[0217]

[0218] [Chemical Formula 2-2]

[0219]

[0220] [Chemical Formula 2-3]

[0221]

[0222] In the above chemical formulas 2-1 to 2-3,

[0223] The definitions of R1, R2, L1 to L3, Ar1, Ar2, a, and b are the same as those in Chemical Formula 1 above.

[0224] In one embodiment of this specification, the above chemical formula 1 is represented by any one of the following chemical formulas 2-1, 2-2 and 2-3-1.

[0225] [Chemical Formula 2-1]

[0226]

[0227] [Chemical Formula 2-2]

[0228]

[0229] [Chemical Formula 2-3-1]

[0230]

[0231] In the above chemical formulas 2-1, 2-2, and 2-3-1,

[0232] The definitions of R1, R2, L1 to L3, Ar1, Ar2 and a are the same as those in the above chemical formula 1.

[0233] In one embodiment of this specification, the above chemical formula 1 is represented by the following chemical formula 3-1 or 3-2.

[0234] [Chemical Formula 3-1]

[0235]

[0236] [Chemical Formula 3-2]

[0237]

[0238] In the above chemical formulas 3-1 and 3-2,

[0239] The definitions of R1, R2, L1 to L3, Ar1, Ar2, a, and b are the same as those in Chemical Formula 1 above.

[0240] In one embodiment of this specification, the above chemical formula 1 is represented by any one of the following compounds.

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261] According to one embodiment of this specification, the compound represented by chemical formula 1 can be manufactured with a core structure as described in reaction formula 1 below. Substituents can be combined using methods known in the art, and the type, position, or number of substituents can be varied according to techniques known in the art.

[0262] <Reaction Formula 1>

[0263]

[0264] In the above reaction formula 1, the definitions of R1 to R2, Ar1 to Ar2, L1 to L3, a and b are the same as those in the above chemical formula 1.

[0265] In the above reaction formula 1, X can be a halogen group such as Cl, Br, or I.

[0266] In the above reaction formula 1, a process for synthesizing a compound with a specific substituent at a specific position is illustrated. However, compounds belonging to the scope of the above chemical formula 1 can be synthesized using starting materials, intermediate materials, etc., known in the art and synthetic methods known in the art.

[0267] In this specification, compounds with various band gaps can be synthesized by introducing various substituents into the core structure of the compound represented by the above chemical formula 1. Furthermore, in this specification, the HOMO and LUMO energy levels of the compound can be tuned by introducing various substituents into the core structure of the structure shown above.

[0268] In addition, this specification provides organic light-emitting devices containing the compounds mentioned above.

[0269] The organic light-emitting device according to this specification is characterized in that it includes: an anode, a cathode, and one or more organic layers disposed between the anode and the cathode, wherein one or more of the organic layers contains a compound represented by the above-described chemical formula 1.

[0270] The organic light-emitting device described in this specification utilizes the compound of the above-mentioned chemical formula 1 to form an organic layer. Otherwise, it can be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0271] The aforementioned compounds can be used to form organic layers not only through vacuum evaporation but also through solution coating in the fabrication of organic light-emitting devices. Here, solution coating refers to methods such as spin coating, dip coating, inkjet printing, screen printing, spray coating, and roll coating, but is not limited to these.

[0272] The organic layers of the organic light-emitting device described in this specification can be formed as a single layer or as a multilayer structure with two or more organic layers stacked on top of each other. For example, the organic light-emitting device of this invention can have a structure comprising one or more of the following as organic layers: a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron injection and transport layer. However, the structure of the organic light-emitting device described in this specification is not limited thereto, and may include fewer or more organic layers.

[0273] In the organic light-emitting device of this specification, the organic layer includes a hole injection layer, a hole transport layer, or a hole injection and transport layer, and the hole injection layer, hole transport layer, or hole injection and transport layer may contain a compound represented by the above-mentioned chemical formula 1.

[0274] In the organic light-emitting device of this specification, the organic layer includes a hole transport layer or a hole injection layer, which may contain a compound represented by the above-described chemical formula 1.

[0275] In one embodiment of this specification, the organic layer includes an electron blocking layer comprising a compound represented by the above-described chemical formula 1.

[0276] In one embodiment of this specification, the organic layer includes an electron injection layer, an electron transport layer, an electron transport and injection layer, or a hole blocking layer, which may contain a compound represented by the above-described chemical formula 1.

[0277] In the organic light-emitting device of this specification, the organic layer includes an electron transport layer, an electron injection layer, or an electron transport and injection layer, and the electron transport layer, electron injection layer, or electron transport and injection layer may contain a compound represented by the above-described chemical formula 1.

[0278] In one embodiment of this specification, the organic layer includes an electronic conditioning layer, which may contain a compound represented by the above-described chemical formula 1.

[0279] In one embodiment of this specification, the organic layer includes a hole-blocking layer comprising a compound represented by the above-described chemical formula 1.

[0280] In the organic light-emitting device of this specification, the organic layer is an electron transport and injection layer, which contains a compound represented by the above-described chemical formula 1.

[0281] In one embodiment of this specification, the thickness of the organic layer containing the compound of Formula 1 is 5 Å to 300 Å, preferably 10 Å to 300 Å, and more preferably 10 Å to 200 Å.

[0282] In one embodiment of this specification, the organic layer includes a light-emitting layer comprising a compound represented by the above-described chemical formula 1.

[0283] In one embodiment of this specification, the organic layer includes a light-emitting layer, which contains a compound represented by the above-described chemical formula 1 as the main component.

[0284] In one embodiment of this specification, the organic layer includes a light-emitting layer, which contains a compound represented by the above-described chemical formula 1 as a dopant.

[0285] In another embodiment, the organic layer may also contain other organic compounds, metals, or metal compounds besides those represented by the above-described chemical formula 1.

[0286] In an organic light-emitting device according to one embodiment of this specification, the light-emitting layer further comprises a fluorescent dopant or a phosphorescent dopant. In this case, the dopant in the light-emitting layer comprises 1 to 50 parts by weight relative to 100 parts by weight of the main body.

[0287] As another example, the aforementioned organic layer includes a light-emitting layer, which contains a compound represented by the aforementioned chemical formula 1 as the main body, and may also contain other main bodies.

[0288] In one embodiment of this specification, the organic layer includes a light-emitting layer, which contains anthracene compounds.

[0289] In one embodiment of this specification, the organic layer includes a light-emitting layer, which contains anthracene compounds as the main component.

[0290] In one embodiment of this specification, the organic layer includes a light-emitting layer, which contains an anthracene compound as the main component and also contains a dopant.

[0291] In one embodiment of this specification, the dopant includes arylamine compounds, heterocyclic compounds containing boron and nitrogen, or Ir complexes, etc.

[0292] In one embodiment of this specification, the organic layer includes a light-emitting layer, which contains an anthracene-based compound as the main component and an arylamine-based compound as a dopant.

[0293] In one embodiment of this specification, the organic light-emitting device may further include one or more organic layers selected from the following: a hole transport layer, a hole injection layer, an electron blocking layer, an electron injection and transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer. In another embodiment of this specification, the organic layers may further include one or more of the following: 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.

[0294] In one embodiment of this specification, the organic light-emitting device includes: an anode, a cathode, and two or more organic layers disposed between the anode and the cathode, wherein at least one of the two or more organic layers contains a compound represented by the above chemical formula 1.

[0295] In one embodiment of this specification, the two or more organic layers mentioned above can be selected from the group consisting of a light-emitting layer, a hole transport layer, a hole injection layer, a hole transport and injection layer, and an electron blocking layer.

[0296] In one embodiment of this specification, the two or more organic layers mentioned above can be selected from the group consisting of a light-emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron modulation layer, and a hole blocking layer.

[0297] In one embodiment of this specification, the aforementioned organic layer comprises two or more electron transport layers, and at least one of the two or more electron transport layers contains a compound represented by the aforementioned chemical formula 1. Specifically, in one embodiment of this specification, the compound represented by the aforementioned chemical formula 1 may be contained in one of the two or more electron transport layers, or it may be contained in each of the two or more electron transport layers.

[0298] In addition, in one embodiment of this specification, when the above-mentioned compound is contained in each of the two or more electron transport layers, the other materials besides the compound represented by the above-mentioned chemical formula 1 may be the same as or different from each other.

[0299] When the organic layer comprising the compound represented by Formula 1 above is an electron transport layer, an electron injection layer, or an electron transport and injection layer, the electron transport layer, electron injection layer, or electron transport and injection layer may further comprise an n-type dopant. The n-type dopant may be a material known in the art, for example, a metal or a metal complex. For example, the electron transport layer comprising the compound represented by Formula 1 above may further comprise LiQ (Lithium Quinolate). According to an example, the compound represented by Formula 1 above and the n-type dopant may be comprised in a weight ratio of 2:8 to 8:2, for example, 4:6 to 6:4.

[0300] According to one example, the compound represented by the above chemical formula 1 and the above-mentioned n-type dopant can be contained in a 1:1 weight ratio.

[0301] In one embodiment of this specification, the aforementioned organic layer comprises two or more hole transport layers, and at least one of the two or more hole transport layers contains a compound represented by the aforementioned chemical formula 1. Specifically, in one embodiment of this specification, the compound represented by the aforementioned chemical formula 1 may be contained in one of the two or more hole transport layers, or it may be contained in each of the two or more hole transport layers.

[0302] Furthermore, in one embodiment of this specification, when the compound represented by the above chemical formula 1 is included in each of the two or more hole transport layers, the other materials besides the compound represented by the above chemical formula 1 may be the same as or different from each other.

[0303] In one embodiment of this specification, the organic layer may include, in addition to an organic layer containing a compound represented by the above-described chemical formula 1, a hole injection layer or a hole transport layer, which contains a compound containing an arylamine group, a carbazole group, or a benzocarbazole group.

[0304] In one embodiment of this specification, the organic light-emitting device may be an organic light-emitting device with an anode, one or more organic layers and a cathode sequentially stacked on a substrate (normal type).

[0305] In one embodiment of this specification, the organic light-emitting device may be an organic light-emitting device with a reverse structure (inverted type) in which a cathode, one or more organic layers and an anode are sequentially stacked on a substrate.

[0306] In the organic light-emitting device of the present invention, the organic layer may include an electron blocking layer, which may use materials known in the art.

[0307] For example, the organic light-emitting device described above can have a stacked structure as shown below, but is not limited to this.

[0308] (1) Anode / hole transport layer / light-emitting layer / cathode

[0309] (2) Anode / hole injection layer / hole transport layer / light emission layer / cathode

[0310] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0311] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0312] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0313] (6) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / cathode

[0314] (7) Anode / hole injection layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode

[0315] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light emission layer / electron transport layer / cathode

[0316] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light emission layer / electron transport layer / electron injection layer / cathode

[0317] (10) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Cathode

[0318] (11) Anode / Hole transport layer / Electron blocking layer / Light emitting layer / Electron transport layer / Electron injection layer / Cathode

[0319] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light emission layer / electron transport layer / cathode

[0320] (13) Anode / Hole injection layer / Hole transport layer / Electron blocking layer / Light emission layer / Electron transport layer / Electron injection layer / Cathode

[0321] (14) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0322] (15) Anode / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0323] (16) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0324] (17) Anode / Hole injection layer / Hole transport layer / Light emission layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0325] The organic light-emitting device structure described in this specification can have the following characteristics: Figure 1 and Figure 2 The structure shown is not limited to this.

[0326] Figure 1 An example is shown of an organic light-emitting device in which a substrate 1, an anode 2, an organic layer 10, and a cathode 9 are sequentially stacked. In the structure described above, the aforementioned compound may be contained in the organic layer 10.

[0327] Figure 2 An example is shown of an organic light-emitting device comprising, in sequence, a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light-emitting layer 6, a hole blocking layer 7, an electron injection and transport layer 8, and a cathode 9. In the structure described above, the aforementioned compound may be contained in the hole injection layer 3, the hole transport layer 4, the electron blocking layer 5, the light-emitting layer 6, the hole blocking layer 7, or the electron injection and transport layer 8.

[0328] In one embodiment of this specification, the electron blocking layer and the light-emitting layer may be disposed adjacent to each other. For example, the electron blocking layer and the light-emitting layer may be physically connected.

[0329] In one embodiment of this specification, the hole transport layer and the electron blocking layer may be disposed adjacent to each other. For example, the hole transport layer and the electron blocking layer may be physically connected.

[0330] The organic light-emitting device described in this specification, except that one or more layers of the organic material contain the aforementioned compound, i.e., the compound represented by the aforementioned chemical formula 1, can be manufactured using materials and methods known in the art.

[0331] When the aforementioned organic light-emitting device comprises a plurality of organic layers, the organic layers may be formed from the same substance or different substances.

[0332] For example, the organic light-emitting device according to this specification can be manufactured as follows: An anode is formed by depositing a metal or a conductive metal oxide or alloy thereof onto a substrate using a PVD (physical vapor deposition) method such as sputtering or electron beam evaporation. Then, an organic layer comprising a hole injection layer, a hole transport layer, a light-emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer is formed on the anode. Finally, a material suitable for use as a cathode is deposited onto the organic layer. Alternatively, an organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material onto a substrate.

[0333] The aforementioned organic layer may further include one or more of the following: a hole transport layer, a hole injection layer, an electron blocking layer, an electron injection and transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole transport and injection layer.

[0334] The aforementioned organic layer can 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 and an electron transport layer, an electron injection layer, and an electron injection and transport layer, but it is not limited to this; it can also be a single-layer structure. Furthermore, the aforementioned organic layer can be manufactured in smaller quantities using various polymer materials and solvent processes other than vapor deposition, such as spin coating, dip coating, blade coating, screen printing, inkjet printing, or thermal transfer.

[0335] The anode described above is the electrode for injecting holes. As the anode material, it is generally preferred to be a material with a high work function in order to enable holes to be smoothly injected into the organic layer. Specific examples of anode materials that can be used in this invention include metals such as vanadium, chromium, copper, zinc, and gold, or their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxo)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0336] The cathode described above is the electrode into which electrons are injected. As a cathode material, it is generally preferred to be a material with a low work function in order to facilitate the injection of electrons into the organic layer. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or their alloys; multilayer structures such as LiF / Al or LiO2 / Al, etc., but are not limited to these.

[0337] The aforementioned hole injection layer facilitates the injection of holes from the anode to the light-emitting layer. The hole injection material is one that can effectively receive holes from the anode at low voltages. Preferably, the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of hole injection materials include, but are not limited to, metalloporphyrins, oligothiophenes, arylamine-based organics, hexanitrile hexaazabenzophenanthrene-based organics, quinacridone-based organics, perylene-based organics, anthraquinones, and conductive polymers based on polyaniline and polythiophene. The thickness of the hole injection layer can range from 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, it has the advantage of preventing a decrease in hole injection characteristics; when it is less than 150 nm, it has the advantage of preventing an increase in driving voltage to improve hole migration when the hole injection layer thickness is too thick.

[0338] The aforementioned hole transport layer facilitates hole transport. Hole transport materials are substances capable of receiving holes from the anode or hole injection layer and transferring them to the light-emitting layer; substances with high hole mobility are suitable. Specific examples include aryl amine-based organic compounds, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but these are not limited to these.

[0339] A hole buffer layer may be further provided between the hole injection layer and the hole transport layer, which may contain materials known in the art for hole injection or transport.

[0340] An electron blocking layer may be disposed between the hole transport layer and the light-emitting layer. The aforementioned compounds or materials known in this art can be used in the electron blocking layer.

[0341] The aforementioned luminescent layer can emit red, green, or blue light and can be formed from phosphorescent or fluorescent substances. The luminescent substance is capable of receiving holes and electrons from the hole transport layer and electron transport layer, respectively, and combining them to emit light in the visible light region; preferably, it is a substance with high quantum efficiency for fluorescence or phosphorescence. Specific examples include 8-hydroxyquinoline aluminum complexes (Alq3); carbazole compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; and benzo[…]. Compounds including azoles, benzothiazoles and benzimidazoles; poly(p-phenylenevinylene) (PPV) polymers; spiro compounds; polyfluorene, fluorene, etc., but not limited to these.

[0342] The main materials for the luminescent layer include aromatic fused-ring derivatives or heterocyclic compounds. Specifically, aromatic fused-ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentanebenzene derivatives, phenanthrene compounds, and fluoranthene compounds, while heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives, but are not limited to these.

[0343] When the emissive layer emits red light, phosphorescent materials such as PIQIr(acac) (bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac) (bis(1-phenylquinoline)acetylacetonateiridium), PQIr (tris(1-phenylquinoline)iridium), PtOEP (octaethylporphyrin platinum), or fluorescent materials such as Alq3 (tris(8-hydroxyquinolino)aluminum) can be used as luminescent dopants, but these are not the only options. When the luminescent layer emits green light, phosphorescent materials such as Ir(ppy)3 (fac tris(2-phenylpyridine)iridium, or fluorescent materials such as Alq3 (tris(8-hydroxyquinoline)aluminum) can be used as luminescent dopants, but these are not the only options. When the luminescent layer emits blue light, phosphorescent materials such as (4,6-F2ppy)2Irpic, or fluorescent materials such as spiro-DPVBi, spiro-6P, stilbene (DSB), stilbene arylene (DSA), PFO-based polymers, and PPV-based polymers can be used as luminescent dopants, but these are not the only options.

[0344] A hole blocking layer can be provided between the electron transport layer and the light-emitting layer, and materials known in this art can be used.

[0345] The aforementioned electron transport layer facilitates electron transport. The electron transport material is one that can effectively receive electrons from the cathode and transfer them to the emitting layer; materials with high electron mobility are suitable. Specific examples include the compounds mentioned above, Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic free radical compounds, and hydroxyflavonoid-metal complexes, but these are not limited to these. The thickness of the electron transport layer can range from 1 to 50 nm. When the thickness of the electron transport layer is greater than 1 nm, it has the advantage of preventing a decrease in electron transport properties; when it is less than 50 nm, it has the advantage of preventing the driving voltage from increasing to enhance electron migration when the electron transport layer is too thick.

[0346] The aforementioned electron injection layer facilitates electron injection. Preferred electron injection materials include compounds that possess electron transport capabilities, effectively inject electrons from the cathode, exhibit excellent electron injection performance for the light-emitting layer or material, prevent excitons generated in the light-emitting layer from migrating to the hole injection layer, and demonstrate excellent thin-film formation ability. Specifically, these include fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiam dioxide, etc. azole, Diazoles, triazoles, imidazoles, perylenetetracarboxylic acid, fluorenemethane, anthrones, and their derivatives, metal coordination compounds, and nitrogen-containing five-membered ring derivatives, but not limited to these.

[0347] Examples of the aforementioned metal coordination compounds include lithium 8-hydroxyquinoline, bis(8-hydroxyquinoline)zinc, bis(8-hydroxyquinoline)copper, bis(8-hydroxyquinoline)manganese, tris(8-hydroxyquinoline)aluminum, tris(2-methyl-8-hydroxyquinoline)aluminum, tris(8-hydroxyquinoline)gallium, bis(10-hydroxybenzo[h]quinoline)beryllium, bis(10-hydroxybenzo[h]quinoline)zinc, bis(2-methyl-8-quinoline)gallium chloride, bis(2-methyl-8-quinoline)(o-cresol)gallium, bis(2-methyl-8-quinoline)(1-naphthol)aluminum, and bis(2-methyl-8-quinoline)(2-naphthol)gallium, but are not limited to these.

[0348] The aforementioned hole-blocking layer is a layer that prevents holes from reaching the cathode, and it can typically be formed using the same conditions as the hole injection layer. Specifically, there are... Diazole or triazole derivatives, phenanthrene-rhein derivatives, BCP, aluminum complexes, etc., but not limited to these.

[0349] Depending on the materials used, the organic light-emitting device according to the present invention can be a top-emitting type, a bottom-emitting type, or a bidirectional-emitting type.

[0350] The following detailed description, using embodiments, aims to provide a more specific explanation of this specification. However, the embodiments described herein can be modified in various ways and are not intended to limit the scope of this application to the embodiments detailed below. These embodiments are provided to provide a more complete explanation of this specification to those skilled in the art.

[0351] <Synthesis example>

[0352] Synthesis Example 1. Synthesis of Compound 1

[0353]

[0354] Toluene (300 ml) was added to N-([1,1'-biphenyl]-4-yl)-4'-(phenanthrene-9-yl)-[1,1'-biphenyl]-4-amine (20.0 g, 40.19 mmol), 6-bromo-7-methyl-1,2,3,4-tetrahydronaphthalene (9.23 g, 40.99 mmol), and sodium tert-butoxide (5.41 g, 56.27 mmol), and the mixture was heated and stirred for 10 minutes. Bis(tri-tert-butylphosphine)palladium (0.10 g, 0.20 mmol) dissolved in toluene (30 ml) was added to the mixture, and the mixture was heated and stirred for 1 hour. After the reaction was complete and filtered, the mixture was separated by chromatography with toluene and water. After removing the solvent, the mixture was recrystallized from ethyl acetate to obtain compound 1 (20.0 g, 77.53% yield). (MS [M+H]) + =642)

[0355] Synthesis Example 2. Synthesis of Compound 2

[0356]

[0357] Compound 2 (25.5 g, 78.58% yield) was obtained by using N-(4-(phenanthrene-9-yl)phenyl)-[1,1'-biphenyl]-4-amine (20.0 g, 47.45 mmol) and 6-bromo-1,1,4,4-tetramethyl-7-phenyl-1,2,3,4-tetrahydronaphthalene (16.61 g, 48.39 mmol) via the same method as in Synthetic Example 1 above. (MS[M+H) + =684)

[0358] Synthesis Example 3. Synthesis of Compound 3

[0359]

[0360] Compound 3 (23.3 g, 78.96% yield) was obtained by using N-(4-(phenanthrene-9-yl)phenyl)-[1,1'-biphenyl]-4-amine (20.0 g, 47.45 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (13.61 g, 48.39 mmol) via the same method as in Synthetic Example 1 above. (MS[M+H) + =622)

[0361] Synthesis Example 4. Synthesis of Compound 4

[0362]

[0363] Compound 4 (22.0 g, 79.48% yield) was obtained by using bis(4-(phenanthrene-9-yl)phenyl)amine (20.0 g, 38.34 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (11.00 g, 39.11 mmol) via the same method as described in Synthetic Example 1 above. (MS[M+H)) + =722)

[0364] Synthesis Example 5. Synthesis of Compound 5

[0365]

[0366] Compound 5 (20.5 g, 78.49% yield) was obtained by using N-(4-(triphenyl-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (20.0 g, 42.41 mmol) and 5-bromo-6-methyl-1,2,3,4-tetrahydronaphthalene (9.74 g, 43.26 mmol) via the same method as in Synthetic Example 1 above. (MS[M+H) + =616)

[0367] Synthesis Example 6. Synthesis of Compound 6

[0368]

[0369] Compound 6 (22.5 g, 78.96% yield) was obtained by using N-(4-(triphenyl-2-yl)phenyl)-[1,1'-biphenyl]-4-amine (20.0 g, 42.41 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (12.17 g, 43.26 mmol) via the same method as in Synthetic Example 1 above. (MS[M+H) + =672)

[0370] Synthesis Example 7. Synthesis of Compound 7

[0371]

[0372] Compound 7 (22.5 g, 77.72% yield) was obtained by using N-(4-(naphthyl-1-yl)phenyl)-[1,1',4',1''-triphenyl]-4-amine (20.0 g, 44.68 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (12.82 g, 45.58 mmol) via the same method as in Synthetic Example 1 above. (MS[M+H) + =648)

[0373] Synthesis Example 8. Synthesis of Compound 8

[0374]

[0375] Compound 8 (27.0 g, 76.68% yield) was obtained by the same method as in Synthetic Example 1 above, using 4-(naphthyl-1-yl)aniline (10.0 g, 45.60 mmol) and 6-(4-chlorophenyl)-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (29.25 g, 93.48 mmol). (MS[M+H) + =772)

[0376] Synthesis Example 9. Synthesis of Compound 9

[0377]

[0378] Compound 9 (23.0 g, 79.16% yield) was obtained using N-([1,1'-biphenyl]-4-yl)-2'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-amine (20.0 g, 41.10 mmol) and 6-(4-chlorophenyl)-7-methyl-1,2,3,4-tetrahydronaphthalene (10.76 g, 41.92 mmol) by the same method as in Synthetic Example 1 above. (MS[M+H) + =707)

[0379] Synthesis Example 10. Synthesis of Compound 10

[0380]

[0381] Compound 10 (21.0 g, 77.44% yield) was obtained using N-(2'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-yl)-[1,1',4',1''-terphenyl]-4-amine (20.0 g, 35.54 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (10.20 g, 36.25 mmol) by the same method as in Synthetic Example 1 above. (MS[M+H) + =763)

[0382] Synthesis Example 11. Synthesis of Compound 11

[0383]

[0384] Compound 11 (25.0 g, 79.72% yield) was obtained using N-([1,1'-biphenyl]-4-yl)-2'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-amine (20.0 g, 41.10 mmol) and 6-(4-chlorophenyl)-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (13.12 g, 41.92 mmol) by the same method as in Synthetic Example 1 above. (MS[M+H) + =763)

[0385] Synthesis Example 12. Synthesis of Compound 12

[0386]

[0387] Compound 12 (24.0 g, 76.53% yield) was obtained using N-([1,1'-biphenyl]-4-yl)-2'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-amine (20.0 g, 41.10 mmol) and 5-(4-chlorophenyl)-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (13.12 g, 41.92 mmol) by the same method as in Synthetic Example 1 above. (MS[M+H) + =763)

[0388] Synthesis Example 13. Synthesis of Compound 13

[0389]

[0390] Compound 13 (24.0 g, 77.96% yield) was obtained using N-([1,1'-biphenyl]-4-yl)-2'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-amine (20.0 g, 41.10 mmol) and 6-bromo-1,1,4,4-tetramethyl-7-phenyl-1,2,3,4-tetrahydronaphthalene (14.39 g, 41.92 mmol) by the same method as in Synthetic Example 1 above. (MS[M+H) + =749)

[0391] Synthesis Example 14. Synthesis of Compound 14

[0392]

[0393] Compound 14 (22.5 g, 79.73% yield) was obtained using N-(4-(dibenzo[b,d]furan-4-yl)phenyl)-[1,1',4',1''-triphenyl]-4-amine (20.0 g, 41.02 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (11.77 g, 41.84 mmol) by the same method as in Synthetic Example 1 above. (MS[M+H) + =688)

[0394] Synthesis Example 15. Synthesis of Compound 15

[0395]

[0396] Compound 15 (21.5 g, 76.83% yield) was obtained by using bis(4-(dibenzo[b,d]furan-4-yl)phenyl)amine (20.0 g, 39.87 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (11.44 g, 40.67 mmol) via the same method as in Synthetic Example 1 above. (MS[M+H) + =702)

[0397] Synthesis Example 16. Synthesis of Compound 16

[0398]

[0399] Compound 16 (22.5 g, 79.69% yield) was obtained using N-([1,1'-biphenyl]-4-yl)-2'-(9H-carbazol-9-yl)-[1,1'-biphenyl]-4-amine (20.0 g, 41.10 mmol) and 6-bromo-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene (11.79 g, 41.92 mmol) by the same method as in Synthetic Example 1 above. (MS[M+H) + =687)

[0400] <Experimental Examples and Comparative Experimental Examples>

[0401] Experimental Example 1-1

[0402] A glass substrate coated with an ITO (indium tin oxide) film at a thickness of 1400 Å was immersed in distilled water containing detergent and ultrasonically washed. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, the ultrasonic washing was repeated twice with distilled water for 10 minutes each time. Following the distilled water washing, the substrate was ultrasonically washed with a solvent of isopropanol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0403] On the prepared ITO transparent electrode, a hole injection layer is formed by thermal vacuum evaporation of a compound represented by the chemical formula HAT to a thickness of 100 Å. On the hole injection layer, as a hole transport layer, a compound represented by the chemical formula HT1 is vacuum-evaporated to a thickness of 1150 Å. Then, as an electron blocking layer, compound 1 prepared in Synthesis Example 1 is thermally vacuum-evaporated to a thickness of 150 Å. Next, as a light-emitting layer, a compound represented by the chemical formula BH and a compound represented by the chemical formula BD are vacuum-evaporated in a weight ratio of 25:1 to a thickness of 200 Å. Next, as a hole blocking layer, a compound represented by the chemical formula HB1 is vacuum-evaporated to a thickness of 50 Å. Finally, as an electron injection and transport layer, a compound represented by the chemical formula ET1 and a compound represented by the chemical formula LiQ are vacuum-evaporated in a weight ratio of 1:1 to a thickness of 310 Å. On the aforementioned electron transport and injection layer, lithium fluoride (LiF) is deposited sequentially with a thickness of 12 Å and aluminum with a thickness of 1000 Å to form a cathode, thereby fabricating an organic light-emitting device.

[0404]

[0405] Experimental Examples 1-2 to 1-16 and Comparative Experimental Examples 1-1 to 1-3

[0406] In Experiment 1-1 above, compound 1 was replaced with the compound listed in Table 1 below. Otherwise, organic light-emitting devices (OLEDs) of Experiment 1-2 to 1-16 and Comparative Experiment 1-1 to 1-3 were fabricated using the same method as in Experiment 1-1. An A / cm² pressure was applied to the OLEDs fabricated in the experimental and comparative experiments. 2 At the given current, voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 1 below. On the other hand, T95 represents the time required for the brightness to decrease from the initial brightness (6000 nits) to 95%.

[0407] [Table 1]

[0408]

[0409]

[0410] As shown in Table 1 above, the compounds of the present invention have been confirmed to have excellent electron blocking capabilities, and their use in organic light-emitting devices with electron blocking layers has shown significant effects in terms of driving voltage, efficiency and lifetime.

[0411] Comparing Experimental Examples 1-1 to 1-16 with Comparative Experimental Examples 1-1 to 1-3 confirmed that the compounds of the present invention, by having alkyl substituents with 1 to 3 carbon atoms on tetrahydronaphthalene and having alkyl or aryl substituents on the benzene ring of tetrahydronaphthalene, can be used in organic light-emitting devices with electron blocking layers to achieve low driving voltage, high efficiency, and long lifetime.

[0412] Experimental Examples 2-1 to 2-10 and Comparative Experimental Examples 1-1, 2-1 to 2-4

[0413] In Experiment 1-1 above, as the electron blocking layer, compound EB1 was used instead of compound 1, and as the hole transport layer, the compound listed in Table 2 below was used instead of the compound HT1. Otherwise, organic light-emitting devices in Experiments 2-1 to 2-10 and Comparative Experiments 2-1 to 2-4 were fabricated using the same method as in Experiment 1-1. A 10 mA / cm² pressure was applied to the organic light-emitting devices fabricated in the experimental and comparative examples. 2 When the current was applied, the voltage, efficiency, color coordinates, and lifetime were measured, and the results are shown in Table 2 below. On the other hand, T95 represents the time required for the brightness to decrease from the initial brightness (6000 nits) to 95%.

[0414] [Table 2]

[0415]

[0416]

[0417] As shown in Table 2 above, the compounds of the present invention have been confirmed to have excellent hole transport capabilities, and their use in organic light-emitting devices with hole transport layers has shown significant effects in terms of driving voltage, efficiency and lifetime.

[0418] Comparing Experimental Examples 2-1 to 2-10 with Comparative Experimental Examples 1-1 and 2-1 to 2-4, it was confirmed that the compounds of the present invention, by having alkyl substituents with 1 to 3 carbon atoms on tetrahydronaphthalene and alkyl or aryl substituents on the benzene ring of tetrahydronaphthalene, can be used in organic light-emitting devices with hole transport layers to achieve low driving voltage, high efficiency, and long lifetime.

Claims

1. A compound represented by the following chemical formula 1: ， In the chemical formula 1, R1 and R2 may be the same as or different from each other, and each may independently be hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. At least one of R1 and R2 is an alkyl group having 1 to 3 carbon atoms. At least one of R2 is an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. Ar1 and Ar2 may be the same as or different from each other, and each is independently a phenyl, biphenyl, terphenyl, naphthyl, phenanthrene, triphenylene, tetrahydronaphthyl, dibenzofuranyl, dibenzothiophene, or carbazolyl group substituted or unsubstituted with deuterium or an alkyl group having 1 to 30 carbon atoms. L1 can be directly bonded, phenylene, or biphenylene. L2 and L3 may be the same as or different from each other, and each is independently a phenylene substituted or unsubstituted with deuterium or an alkyl group having 1 to 30 carbon atoms, or a biphenylene substituted or unsubstituted with deuterium or an alkyl group having 1 to 30 carbon atoms. When a is an integer from 1 to 8, and a is 2 or higher, R1 is either the same or different from each other. When b is an integer from 1 to 3, and b is 2 or more, R2 is either the same or different from each other.

2. The compound according to claim 1, wherein, Chemical Formula 1 is represented by the following Chemical Formula 1-1: ， In the chemical formula 1-1, The definitions of L1 to L3, Ar1, Ar2, and a are the same as those in Chemical Formula 1. R1 is hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. At least one of R1 and R3 is an alkyl group having 1 to 3 carbon atoms. R3 is an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

3. The compound according to claim 1, wherein, Chemical Formula 1 is represented by any one of the following Chemical Formulas 2-1 to 2-3: ， In the chemical formulas 2-1 to 2-3, The definitions of L1 to L3, Ar1, Ar2, a, and b are the same as those in Chemical Formula 1. R1 and R2 may be the same as or different from each other, and each may independently be hydrogen, deuterium, an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms. At least one of R2 is an alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 carbon atoms.

4. The compound according to claim 1, wherein, The chemical formula 1 is represented by the following chemical formula 3-1 or 3-2: ， In the chemical formulas 3-1 and 3-2, The definitions of R1, R2, L1 to L3, Ar1, Ar2, a, and b are the same as those in Chemical Formula 1.

5. The compound according to claim 1, wherein, Chemical Formula 1 is represented by any of the following compounds: 。 6. An organic light-emitting device, wherein, include: 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 comprises the compound according to any one of claims 1 to 5.

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

8. The organic light-emitting device according to claim 6, wherein, The organic layer includes an electron blocking layer, which contains the compound.

9. The organic light-emitting device according to claim 6, wherein, The organic layer includes one or more of the following: a hole transport layer, a hole injection layer, an electron blocking layer, a hole 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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