Organic compound and organic light emitting device comprising same

Abstract

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

Description

Technology Field

[0001] The present invention claims the benefit of the filing date of Korean Patent Application No. 10-2025-0015696 filed with the Korean Intellectual Property Office on February 7, 2025, the entire contents of which are incorporated herein.

[0002] This specification relates to organic compounds and organic light-emitting diodes containing the same. Background Technology

[0003] Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting diodes (OLEDs) that utilize this phenomenon typically have a structure comprising an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure made of different materials to enhance the efficiency and stability of the OLED; for example, it may consist of a hole injection layer, a hole transport layer, an emissive layer, an electron transport layer, and an electron injection layer. In the structure of such an OLED, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode into the organic layer. When the injected holes and electrons meet, an exciton is formed, and light is emitted when this exciton returns to the ground state.

[0004] The development of new materials for organic light-emitting diodes as described above is continuously required. The problem to be solved

[0005] The present specification provides an organic compound and an organic light-emitting diode containing the same. means of solving the problem

[0006] One embodiment of the present specification provides an organic compound represented by the following chemical formula 1.

[0007] [Chemical Formula 1]

[0008]

[0009] In the above chemical formula 1,

[0010] R1 to R8 are the same or different from one another, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and

[0011] L1 and L2 are the same or different from each other, and each is independently directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0012] A2 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0013] A1 is a substituent represented by the following chemical formula A, and

[0014] [Chemical Formula A]

[0015]

[0016] In the above chemical formula A,

[0017] A3 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0018] n is an integer from 1 to 5, and

[0019] represents the region connected to L1.

[0020] In addition, one embodiment of the present specification provides an organic light-emitting device comprising an anode; a cathode; and one or more organic layers provided between the anode and the cathode, wherein one or more of the organic layers comprise the aforementioned compound. Effects of the invention

[0021] The organic compounds described in this specification may be used as materials for the organic layer of an organic light-emitting device. An organic compound according to at least one embodiment of this specification may improve efficiency, lower driving voltage, and / or lifespan characteristics in an organic light-emitting device. Brief explanation of the drawing

[0022] FIGS. 1 and 2 illustrate examples of organic light-emitting devices according to one embodiment of the present specification. Specific details for implementing the invention

[0023] The present specification will be described in more detail below.

[0024] In this specification, when a part is described as "comprising" a certain component, this means that, unless specifically stated otherwise, it does not exclude other components but may include additional components.

[0025] In this specification, when it is said that a member is located "on" another member, this includes not only cases where a member is in contact with another member, but also cases where another member exists between the two members.

[0026] In this specification, HOMO (highest occupied molecular orbital) refers to the highest energy region in the area where electrons can participate in bonding, LUMO (lowest unoccupied molecular orbital) refers to the lowest energy region in the antibonding area, and HOMO energy level refers to the distance from the vacuum level to the HOMO. Additionally, LUMO energy level refers to the distance from the vacuum level to the LUMO.

[0027] In this specification, bandgap refers to the difference in energy levels between HOMO and LUMO, i.e., the HOMO-LUMO gap.

[0028] In this specification, HOMO energy levels can be measured using an atmospheric photoelectron spectrometer (manufactured by RIKEN KEIKI Co., Ltd.: AC3), and LUMO energy levels can be calculated from wavelength values ​​measured through photoluminescence (PL).

[0029] In this specification, the term “combination thereof” included in a Markush-type expression means one or more mixtures or combinations selected from a group consisting of components described in the Markush-type expression, and means including one or more selected from the group consisting of said components.

[0030] Examples of substituents in this specification are described below, but are not limited thereto.

[0031] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the substitution site is not limited to the site where the hydrogen atom is substituted, that is, any site where a substituent can be substituted, and in the case of two or more substitutions, the two or more substituents may be the same or different from each other.

[0032] In this specification, the term “substituted or unsubstituted” means that it is substituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group (-CN); silyl group; alkyl group; cycloalkyl group; alkoxy group; aryloxy group; alkyl sulfoxy group; aryl sulfoxy group; alkyl sulfoxy group; aryl sulfoxy group; alkenyl group; amine group; aryl group; or heterocyclic group, or is substituted with a substituent in which two or more of the exemplified substituents are connected, or has no substituents. For example, “a substituent in which two or more substituents are connected” may be a biphenyl group. That is, the biphenyl group may be an aryl group, or it may be interpreted as a substituent in which two phenyl groups are connected.

[0033] In this specification, the term “substituted or unsubstituted” means that it is substituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group; nitro group; hydroxyl group; amino group; alkoxy group; aryloxy group; alkyl group; cycloalkyl group; alkenyl group; alkynyl group; aryl group; and heterocyclic group, or is substituted with a substituent in which two or more of the exemplified substituents are connected, or has no substituents.

[0034] In this specification, the term “substituted or unsubstituted” means that it is substituted with one or more substituents selected from the group consisting of deuterium; halogen group; nitrile group; alkyl group; aryl group; and heterocyclic group, or that it is substituted with two or more of the exemplified substituents linked together, or that it has no substituents.

[0035] Examples of the above substituents are described below, but are not limited thereto.

[0036] In this specification, examples of halogen groups include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0037] In the present specification, the silyl group may be represented by the chemical formula -SiYaYbYc, and Ya, Yb, and Yc may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specifically, the silyl group may be a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, a phenylsilyl group, etc., but is not limited thereto.

[0038] In the present specification, the alkyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. Specific examples of alkyl groups include, butyl, n-butyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, pentyl, n-pentyl, hexyl, n-hexyl, heptyl, n-heptyl, octyl, n-octyl, etc., but are not limited thereto.

[0039] In the present specification, the alkoxy group may be a straight chain, a branched chain, or a cyclic chain. The number of carbon atoms in the alkoxy group is not particularly limited, but it is preferred to have 1 to 20 carbon atoms. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but is not limited thereto.

[0040] Substituents comprising alkyl groups, alkoxy groups and other alkyl groups described in this specification include both straight-chain and broken-chain forms.

[0041] In the present specification, the alkenyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to yet another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. 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, stilbenyl group, styrenyl group, etc., but are not limited to these.

[0042] In the present specification, the alkynyl group is a substituent comprising a triple bond between carbon atoms, and may be a straight chain or a branched chain. The number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkynyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkynyl group is 2 to 10.

[0043] In the present specification, the cycloalkyl group is not particularly limited, but it is preferable that it has 3 to 60 carbon atoms, and according to one embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 30. According to another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 20. According to yet another embodiment, the number of carbon atoms of the cycloalkyl group is 3 to 6. Specifically, cyclopropyl groups, cyclobutyl groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, etc., are included but are not limited thereto.

[0044] In this specification, the amine group is -NH2, and the amine group may be substituted with the aforementioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The number of carbon atoms in the substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the number of carbon atoms in the amine group is 1 to 20. According to one embodiment, the number of carbon atoms in the amine group is 1 to 10. Specific examples of substituted amine groups include, but are not limited to, methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, 9,9-dimethylfluorenylphenylamine, pyridylphenylamine, diphenylamine, phenylpyridylamine, naphthylamine, biphenylamine, anthracenylamine, dibenzofuranylphenylamine, 9-methylanthracenylamine, diphenylamine, phenylnaphthylamine, ditolylamine, phenyltolylamine, and diphenylamine groups.

[0045] In the present specification, the substituted aryl group may include a structure in which an aliphatic hydrocarbon ring is condensed to the aryl group. According to one embodiment, the substituted aryl group may include a tetrahydronaphthalene group, and more specifically, It may include (1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene group), but is not limited thereto.

[0046] In the present specification, the fluorenyl group may be substituted, and two substituents may be combined to form a spiro structure. In this case, the spiro structure may be an aromatic hydrocarbon ring or an aliphatic hydrocarbon ring.

[0047] When the above fluorenyl group is substituted, , , Spirofluorenyl group of the back, etc. (9,9-dimethylfluorenyl group), and It can be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group). However, it is not limited to this.

[0048] In this specification, the aryl group among the aryloxy group and the arylamine group may be subject to the description of the aryl group described above.

[0049] In this specification, the description regarding the alkyl group described above may be applied to the alkyl group among the alkyl thioxy group and the alkyl sulfoxy group.

[0050] In the present specification, the heterocyclic group is a ring group comprising one or more heteroatoms N, O, P, S, Si, and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20. Examples of heterocyclic groups include, but are not limited to, pyridine groups, pyrrole groups, pyrimidine groups, quinoline groups, pyridazinyl groups, furan groups, thiophene groups, imidazole groups, pyrazol groups, dibenzofuran groups, dibenzothiophene groups, carbazole groups, benzocarbazole groups, naphthobenzofuran groups, benzonaphthiophene groups, indenocarbazole groups, triazinyl groups, etc.

[0051] In this specification, the description of the aforementioned heterocyclic group may apply, except that the heteroaryl group is aromatic.

[0052] In this specification, the description of the aryl group may apply except that the arylene group is divalent.

[0053] In this specification, the description of the heteroaryl group may apply except that the heteroaryl group is divalent.

[0054] In the present specification, in a substituted or unsubstituted ring formed by combining adjacent groups, "ring" means a hydrocarbon ring; or a heteroring.

[0055] For example, when adjacent groups combine to form a ring, a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heteroring; a substituted or unsubstituted aromatic heteroring; or a condensed ring thereof may be formed. The hydrocarbon ring refers to a ring composed only of carbon and hydrogen atoms. The heteroring refers to a ring containing one or more elements selected from N, O, P, S, Si, and Se. In this specification, the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heteroring, and aromatic heteroring may be monocyclic or polycyclic.

[0056] In this specification, an aliphatic hydrocarbon ring refers to a non-aromatic ring composed only of carbon and hydrogen atoms. Examples of aliphatic hydrocarbon rings include, but are not limited to, cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, and cyclooctene.

[0057] In this specification, an aromatic hydrocarbon ring refers to an aromatic ring composed only of carbon and hydrogen atoms. Examples of aromatic hydrocarbon rings include, but are not limited to, benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, chrysene, pentacene, fluorene, indene, acenaphthylene, benzofluorene, and spirofluorene. In this specification, an aromatic hydrocarbon ring may be interpreted as having the same meaning as an aryl group.

[0058] In this specification, an aliphatic heterocycle means an aliphatic ring containing one or more heteroatoms. Examples of aliphatic heterocycles include, but are not limited to, oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxephane, azocaine, thiocane, etc.

[0059] In this specification, an aromatic heterocycle means an aromatic ring comprising one or more heteroatoms. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parazol, oxazole, isooxazole, thiazole, isothiazole, triazole, oxadiazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazolin, quinoxaline, naphthiridine, acridine, phenanthridine, diazanaphthalene, driazindene, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, Examples include imidazopyridine, phenoxazine, indolocarbazole, indenocabazole, etc., but are not limited to these.

[0060] In this specification, This means that the structure inside the parentheses contains n deuterium atoms.

[0061] Preferred embodiments of the present invention are described in detail below. However, embodiments of the present invention may be modified in various forms, and the scope of the present invention is not limited to the embodiments described below.

[0062] An organic compound according to one embodiment of the present specification is represented by the following chemical formula 1. In particular, by introducing a naphthoxazole-based substituent into an anthracene core, the electron transfer rate is accelerated to exhibit low voltage characteristics. Additionally, by bonding an aryl group or a heteroaryl group to the naphthoxazole-based substituent, the stability of the substituent is increased, thereby achieving long life characteristics. Furthermore, by substituting at least one deuterium into the naphthoxazole-based substituent, the stability of the molecule is increased, which can enhance the long life characteristics.

[0063] The organic compound of Chemical Formula 1 below will be described in detail below.

[0064] [Chemical Formula 1]

[0065]

[0066] In the above chemical formula 1,

[0067] R1 to R8 are the same or different from one another, and each is independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, and

[0068] L1 and L2 are the same or different from each other, and each is independently directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0069] A2 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0070] A1 is a substituent represented by the following chemical formula A, and

[0071] [Chemical Formula A]

[0072]

[0073] In the above chemical formula A,

[0074] A3 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and

[0075] n is an integer from 1 to 5, and

[0076] represents the region connected to L1.

[0077] In one embodiment of the present specification, R1 to R8 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0078] The above R1 to R8 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0079] The above R1 to R8 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted methyl group; a substituted or unsubstituted ethyl group; a substituted or unsubstituted propyl group; a substituted or unsubstituted butyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted naphthyl group.

[0080] In one embodiment of the present specification, R1 to R8 are the same or different from one another and are each independently hydrogen; or deuterium.

[0081] In one embodiment of the present specification, R1 to R8 are all deuterium.

[0082] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted arylene group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms.

[0083] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted arylene group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms.

[0084] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently direct bonded; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

[0085] In one embodiment of the present specification, L1 and L2 are the same or different from each other and are each independently directly bonded; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0086] In one embodiment of the present specification, A2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0087] In one embodiment of the present specification, A2 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

[0088] In one embodiment of the present specification, A2 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a heteroaryl group having 3 to 20 carbon atoms comprising N, O, or S as a substituted or unsubstituted heteroelement.

[0089] In one embodiment of the present specification, A2 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophen group; or a substituted or unsubstituted carbazole group.

[0090] In one embodiment of the present specification, A2 is a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthrenyl group substituted or unsubstituted with deuterium; a 9,9-dimethylfluorenyl group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; a dibenzothiophene group substituted or unsubstituted with deuterium; or a carbazole group substituted or unsubstituted with deuterium.

[0091] In one embodiment of the present specification, A2 is a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; or a dibenzothiophene group substituted or unsubstituted with deuterium.

[0092] In one embodiment of the present specification, A3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0093] In one embodiment of the present specification, A3 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms.

[0094] In one embodiment of the present specification, A3 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted benzofuran group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted benzothiophen group; or a substituted or unsubstituted dibenzothiophen group.

[0095] In one embodiment of the present specification, A3 is a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthrenyl group substituted or unsubstituted with deuterium; a 9,9-dimethylfluorenyl group substituted or unsubstituted with deuterium; a benzofuran group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; a benzothiophene group substituted or unsubstituted with deuterium; or a dibenzothiophene group substituted or unsubstituted with deuterium.

[0096] In one embodiment of the present specification, the formula A is represented by any one of the following formulas A-1 to A-3:

[0097] [Chemical Formula A-1]

[0098]

[0099] [Chemical Formula A-2]

[0100]

[0101] [Chemical Formula A-3]

[0102]

[0104] In the above chemical formulas A-1 to A-3,

[0105] Any one of R9 to R14 is connected to L1, and

[0106] The substituents among R9 to R14 that are not connected to L1 are the same or different from one another, and each is independently hydrogen or deuterium, and

[0107] At least one of R9 to R14 is deuterium, and

[0108] The definition of A3 above is the same as the definition in the above chemical formula A.

[0109] In one embodiment of the present specification, all substituents among R9 to R14 that are not connected to L1 are deuterium.

[0110] In one embodiment of the present specification, the formula 1 is represented by any one of the following compounds.

[0111]

[0112]

[0113]

[0114]

[0115] A compound represented by Formula 1 according to one embodiment of this specification may have a core structure prepared as described in the following manufacturing example. Substituents may be bonded by methods known in the art, and the type, position, or number of substituents may be changed according to techniques known in the art. Specifically, compounds corresponding to the range of Formula 1 may be synthesized by synthesis methods known in the art using starting materials, intermediate materials, etc. known in the art.

[0116] In this specification, compounds having various energy band gaps can be synthesized by introducing various substituents into the core structure of a compound represented by Chemical Formula 1. In addition, in this specification, the HOMO and LUMO energy levels of a compound can also be controlled by introducing various substituents into the core structure of such a structure.

[0117] In addition, the present specification provides an organic light-emitting device comprising the compound described above.

[0118] In this specification, the term "layer" is used in a sense compatible with "film" as is commonly used in the art, and refers to a coating that covers a target area. The size of the "layer" is not limited, and each "layer" may have the same or different sizes. According to one embodiment, the size of the "layer" may be equal to the size of the entire device, correspond to the size of a specific functional area, or be as small as a single subpixel.

[0119] In the present specification, the meaning of a specific A substance being included in a B layer includes both i) one or more types of A substances being included in a single B layer and ii) the B layer being composed of one or more layers and A substance being included in one or more layers among the multilayer B layers.

[0120] In the present specification, the meaning that a specific A material is included in a C layer or a D layer is that it is included in at least one of the C layers, ii) included in at least one of the D layers, or iii) included in each of the C layers and the D layers.

[0121] An organic light-emitting device according to the present specification comprises an anode; a cathode; and one or more organic layers provided between the anode and the cathode, wherein one or more of the organic layers comprise a compound represented by the aforementioned chemical formula 1.

[0122] The organic light-emitting device of the present specification can be manufactured by conventional methods and materials for manufacturing organic light-emitting devices, except for forming an organic layer using the compound of Formula 1 described above.

[0123] The above compound can be formed as an organic layer by vacuum deposition as well as by solution coating when manufacturing an organic light-emitting device. Here, solution coating refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited to these.

[0124] The organic layer of the organic light-emitting device of the present specification may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are stacked. For example, the organic light-emitting device of the present invention may have a structure comprising one or more layers among a hole transport layer, a hole injection layer, an electron blocking layer, a hole transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer as organic layers. However, the structure of the organic light-emitting device of the present specification is not limited thereto and may include a smaller or larger number of organic layers.

[0125] In one embodiment of the present specification, the thickness of the organic layer containing the compound of Formula 1 may be 5 Å to 2000 Å or 5 Å to 500 Å, and preferably 10 Å to 400 Å.

[0126] In another embodiment, the organic layer may further include other organic compounds, metals, or metal compounds in addition to the compound represented by the aforementioned chemical formula 1.

[0127] In one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer may comprise a compound represented by the aforementioned chemical formula 1.

[0128] In one embodiment of the present specification, the light-emitting layer may be a blue light-emitting layer, a red light-emitting layer, or a green light-emitting layer.

[0129] In one embodiment of the present specification, the light-emitting layer may be a blue light-emitting layer.

[0130] In one embodiment of the present specification, the light-emitting layer may have a light-emitting peak within the range of 400 nm to 470 nm.

[0131] In one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer may include a compound represented by the aforementioned chemical formula 1 as a host.

[0132] In one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a compound represented by the aforementioned chemical formula 1 as a host and may further comprise a dopant. Specifically, the dopant may be a fluorescent dopant or a phosphorescent dopant.

[0133] In one embodiment of the present specification, the light-emitting layer may include a host and a dopant in a weight ratio of 99:1 to 1:99. Specifically, it may include a weight ratio of 99:1 to 50:50, a weight ratio of 99:1 to 70:30, a weight ratio of 99:1 to 80:20, a weight ratio of 99:1 to 90:10, or a weight ratio of 99:1 to 95:5.

[0134] In one embodiment of the present specification, the dopant may include an arylamine compound, a heterocyclic compound containing boron and nitrogen, a metal complex compound, a platinum complex compound or an iridium complex compound, etc.

[0135] For example, when the light-emitting layer emits blue light, phosphorescent materials such as platinum complex compounds and (4,6-F2ppy)2Irpic, or fluorescent materials such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distrylarylene (DSA), PFO-based polymers, and PPV-based polymers may be used as light-emitting dopants, but are not limited to these.

[0136] In one embodiment of the present specification, the dopant is a metal complex compound.

[0137] In one embodiment of the present specification, the dopant is a platinum complex compound.

[0138] In one embodiment of the present specification, the dopant is an iridium complex compound.

[0139] In one embodiment of the present specification, the dopant may include a compound represented by the following chemical formula D-1 or D-2, but is not limited thereto.

[0140] [Chemical Formula D-1]

[0141]

[0142] [Chemical Formula D-2]

[0143]

[0144] In the above chemical formula D-1,

[0145] Y1 and Y2 are the same or different from each other, and each is independently CR' or NR", and at least one of Y1 and Y2 is NR",

[0146] Z1 and Z2 are the same or different from each other and are each independently a substituted or unsubstituted five-membered ring; a substituted or unsubstituted six-membered ring; or a ring formed by the condensation of a substituted or unsubstituted five-membered and six-membered ring, and

[0147] R401, R' and R" are the same or different from each other, and each independently is hydrogen; deuterium; a halogen group; a nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted silyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group, or is bonded to adjacent groups to form a substituted or unsubstituted ring, and

[0148] r401 is an integer from 0 to 3, and if r401 is 2 or greater, the substituents within the parentheses are the same or different, and

[0149] In the above chemical formula D-2,

[0150] X11 and X12 are N,

[0151] R501 to R504 are the same or different from one another, and each independently is hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; or a substituted or unsubstituted aryl group, and

[0152] r501 and r502 are each integers from 0 to 4, and

[0153] r503 and r504 are integers from 0 to 3, respectively, and

[0154] If r501 to r504 are each 2 or more, the 2 or more R501 to R504 are each the same or different from each other.

[0155] In one embodiment of the present specification, Y1 and Y2 are both NR" and R" is a substituted or unsubstituted aryl group.

[0156] In one embodiment of the present specification, Y1 and Y2 are both NR", and R" is an aryl group substituted or unsubstituted with an alkyl group.

[0157] In one embodiment of the present specification, Y1 and Y2 are both NR", and R" is an aryl group substituted or unsubstituted with a tert-butyl group.

[0158] In one embodiment of the present specification, Z1 is a substituted or unsubstituted phenyl group.

[0159] In one embodiment of the present specification, Z1 is a phenyl group substituted or unsubstituted with an alkyl group.

[0160] In one embodiment of the present specification, Z1 is a phenyl group substituted or unsubstituted with a tert-butyl group.

[0161] In one embodiment of the present specification, Z2 is a substituted or unsubstituted phenyl group or a substituted or unsubstituted benzothiophene group.

[0162] In one embodiment of the present specification, Z2 is a phenyl group substituted or unsubstituted with an alkyl group or a benzothiophene group substituted or unsubstituted with an alkyl group.

[0163] In one embodiment of the present specification, Z2 is a phenyl group substituted or unsubstituted with a tert-butyl group or a benzothiophene group substituted or unsubstituted with a tert-butyl group.

[0164] In one embodiment of the present specification, the R401 is a substituted or unsubstituted alkyl group.

[0165] In one embodiment of the present specification, the R401 is a methyl group.

[0166] In one embodiment of the present specification, the R401 is a substituted or unsubstituted amine group.

[0167] In one embodiment of the present specification, R501 and R502 are substituted or unsubstituted alkyl groups.

[0168] In one embodiment of the present specification, R501 and R502 are substituted or unsubstituted tert-butyl groups.

[0169] In one embodiment of the present specification, R503 and R504 are substituted or unsubstituted amine groups.

[0170] In one embodiment of the present specification, the dopant may be represented by the following compounds, but is not limited thereto.

[0171]

[0172] As another example, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises a compound represented by Chemical Formula 1 as a host, and may further comprise additional hosts.

[0173] The organic light-emitting device of the present specification may further include one or more organic layers among a hole transport layer, a hole injection layer, an electron blocking layer, an electron transport and injection layer, an electron transport layer, an electron injection layer, a hole blocking layer, and a hole injection and transport layer.

[0174] In one embodiment of the present specification, the organic light-emitting element comprises an anode; a cathode; and two or more organic layers provided between the anode and the cathode, and at least one of the two or more organic layers comprises a compound represented by Formula 1.

[0175] In one embodiment of the present specification, the two or more organic layers may be selected from the group consisting of a light-emitting layer, a hole transport layer, a hole injection layer, a hole transport and injection layer, and an electron blocking layer.

[0176] In one embodiment of the present specification, the two or more organic layers may be selected from the group consisting of a light-emitting layer, an electron transport layer, an electron injection layer, an electron transport and injection layer, an electron control layer, and a hole blocking layer.

[0177] In one embodiment of the present specification, the organic light-emitting device may be an organic light-emitting device of a normal type structure in which an anode, one or more organic layers, and a cathode are sequentially stacked on a substrate.

[0178] In one embodiment of the present specification, the organic light-emitting device may be an inverted type organic light-emitting device in which a cathode, one or more organic layers, and an anode are sequentially stacked on a substrate.

[0179] The above organic light-emitting device may have a stacked structure such as, for example, the following, but is not limited thereto.

[0180] (1) Anode / hole transport layer / emissive layer / cathode

[0181] (2) Anode / hole injection layer / hole transport layer / emissive layer / cathode

[0182] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / cathode

[0183] (4) Anode / hole transport layer / emissive layer / electron transport layer / cathode

[0184] (5) Anode / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0185] (6) Anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / cathode

[0186] (7) Anode / hole injection layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0187] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / electron transport layer / cathode

[0188] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / emissive layer / electron transport layer / electron injection layer / cathode

[0189] (10) Anode / hole transport layer / hole control layer / emissive layer / electron transport layer / cathode

[0190] (11) Anode / hole transport layer / hole control layer / emissive layer / electron transport layer / electron injection layer / cathode

[0191] (12) Anode / hole injection layer / hole transport layer / hole control layer / emissive layer / electron transport layer / cathode

[0192] (13) Anode / hole injection layer / hole transport layer / hole control layer / emissive layer / electron transport layer / electron injection layer / cathode

[0193] (14) Anode / hole transport layer / emissive layer / electron control layer / electron transport layer / cathode

[0194] (15) Anode / hole transport layer / emissive layer / electron control layer / electron transport layer / electron injection layer / cathode

[0195] (16) Anode / hole injection layer / hole transport layer / emissive layer / electron control layer / electron transport layer / cathode

[0196] (17) Anode / hole injection layer / hole transport layer / emissive layer / electron control layer / electron transport layer / electron injection layer / cathode

[0197] (18) Anode / hole injection layer / hole transport layer / hole control layer / emissive layer / electron control layer / electron transport and injection layer / cathode

[0198] (19) Anode / hole injection layer / hole transport layer / hole control layer / emissive layer / electron control layer / electron transport and injection layer / cathode / capping layer

[0199] The structure of the organic light-emitting device of the present specification may have a structure such as that shown in FIGS. 1 to 2, but is not limited thereto.

[0200] FIG. 1 illustrates the structure of an organic light-emitting device in which a substrate (1), an anode (2), a light-emitting layer (6), and a cathode (10) are sequentially stacked. In such a structure, the compound may be included in the light-emitting layer (6).

[0201] FIG. 2 illustrates the structure of an organic light-emitting device in which a substrate (1), an anode (2), a hole injection layer (3), a hole transport layer (4), a hole control layer (5), a light-emitting layer (6), an electron control layer (7), an electron transport layer (8), an electron injection layer (9), a cathode (10), and a capping layer (11) are sequentially stacked. In such a structure, the compound may be included in any one of the hole injection layer (3), the hole transport layer (4), the hole control layer (5), the light-emitting layer (6), the electron control layer (7), the electron transport layer (8), and the electron injection layer (9), for example, in the light-emitting layer (6).

[0202] In one embodiment of the present specification, the hole transport layer and the light-emitting layer may be provided adjacent to each other. For example, the hole transport layer and the light-emitting layer may be provided in physical contact.

[0203] In one embodiment of the present specification, the hole control layer and the light-emitting layer may be provided adjacently. For example, the hole control layer and the light-emitting layer may be provided in physical contact.

[0204] In one embodiment of the present specification, the hole transport layer and the hole control layer may be provided adjacently. For example, the hole transport layer and the hole control layer may be provided in physical contact.

[0205] The organic light-emitting device of the present specification may be manufactured using materials and methods known in the art, except that one or more of the organic layers comprise the compound, i.e., the compound represented by Chemical Formula 1.

[0206] When the above organic light-emitting element includes a plurality of organic layers, the organic layers may be formed of the same material or different materials.

[0207] For example, an organic light-emitting device according to the present specification can be manufactured by using a physical vapor deposition (PVD) method, such as sputtering or electron beam evaporation, to deposit a metal or a conductive metal oxide or an alloy thereof on a substrate to form an anode, then forming an organic layer including a hole injection layer, a hole transport layer, an emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0208] The above organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a hole injection and transport layer, a hole control layer, an emitting layer and an electron transport layer, an electron injection layer, an electron transport and injection layer, etc., but is not limited thereto and may have a single layer structure. In addition, the above organic layer may be manufactured with a smaller number of layers by using various polymer materials and a solvent process rather than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

[0209] The above anode is an electrode that injects holes, and as the anode material, it is generally preferable to use an organic layer with a high work function to facilitate hole injection. Specific examples of anode materials that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited to these.

[0210] The above cathode is an electrode for injecting electrons, and the cathode material is typically an organic layer, preferably a material with a low work function to facilitate electron injection. Specific examples of cathode materials include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayer materials such as LiF / Al or LiO2 / Al, but are not limited to these.

[0211] The hole injection layer described above is a layer that facilitates the injection of holes from the anode to the light-emitting layer. The hole injection material is a material capable of receiving holes well from the anode at low voltage, and it is preferable that 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 metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile-hexaazatriphenylene-based organic materials, tetrafluorobenzonitrile-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinone, and conductive polymers of polyaniline and polythiophene series, but are not limited to these. The thickness of the hole injection layer may be 1 Å to 150 Å. If the thickness of the hole injection layer is 1 Å or more, there is an advantage in that the hole injection characteristics can be prevented from deteriorating, and if it is 150 Å or less, there is an advantage in that the driving voltage can be prevented from increasing to improve the movement of holes because the thickness of the hole injection layer is too thick.

[0212] According to one embodiment of the present specification, the hole injection layer comprises a compound represented by the following chemical formula HT-1, but is not limited thereto.

[0213] [Chemical Formula HT-1]

[0214]

[0215] In the above chemical formula HT-1,

[0216] At least one of X'1 to X'6 is N, and the rest are CH, and

[0217] R309 to R314 are the same or different from each other and are each independently hydrogen; deuterium; cyano group; substituted or unsubstituted alkyl group; substituted or unsubstituted amine group; substituted or unsubstituted aryl group; or substituted or unsubstituted heteroaryl group, or are combined with adjacent groups to form a substituted or unsubstituted ring.

[0218] According to one embodiment of the present specification, X'1 to X'6 are N.

[0219] According to one embodiment of the present specification, R309 to R314 are cyano groups.

[0220] According to one embodiment of the present specification, the formula HT-1 may include the following compounds, but is not limited thereto.

[0221]

[0222] In one embodiment of the present specification, the hole injection material may include an organic material of the hexanitrile-hexaazatriphenylene series, and specifically, may include hexanitrile-hexaazatriphenylene substituted with a nitrile group.

[0223] The hole transport layer described above can play a role in facilitating the transport of holes. Suitable hole transport materials are those capable of receiving holes from the anode or hole injection layer and transferring them to the emissive layer, provided they possess high mobility for holes. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited to these.

[0224] In one embodiment of the present specification, the hole transport material may include an arylamine-based compound containing a carbazole group.

[0225] The hole transport layer described above can play a role in facilitating the transport of holes. Suitable hole transport materials are those capable of receiving holes from the anode or hole injection layer and transferring them to the emissive layer, provided they possess high mobility for holes. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions, but are not limited to these.

[0226] According to one embodiment of the present specification, the hole transport layer comprises a compound represented by the following chemical formula HT-2, but is not limited thereto.

[0227] [Chemical Formula HT-2]

[0228]

[0229] In the above chemical formula HT-2,

[0230] R315 to R317 are the same or different from one another and are each independently selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; a substituted or unsubstituted amine group and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring, and

[0231] r315 is an integer from 1 to 5, and if r315 is 2 or more, the 2 or more R315s are the same or different from each other,

[0232] r316 is an integer from 1 to 5, and if r316 is 2 or more, the 2 or more R316s are the same or different from each other.

[0233] According to one embodiment of the present specification, R317 may be any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a combination thereof.

[0234] According to one embodiment of the present specification, the R317 may be any one selected from the group consisting of a carbazole group; a phenyl group; a biphenyl group; a triphenylene group; and combinations thereof.

[0235] According to one embodiment of the present specification, R315 and R316 may be the same or different from each other and may each be an independently substituted or unsubstituted aryl group.

[0236] According to one embodiment of the present specification, R315 and R316 may be the same or different from each other and may each independently be a phenyl group, a naphthyl group or a biphenyl group.

[0237] According to one embodiment of the present specification, the compound of formula HT-2 may include one or more of the following compounds, but is not limited thereto.

[0238] ,

[0239] The hole control layer described above is a layer capable of improving the lifespan and efficiency of a device by controlling holes transported from the hole transport layer to be smoothly injected into the light-emitting layer and preventing electrons injected from the electron injection layer from passing through the light-emitting layer and entering the hole injection layer. It may be formed between the light-emitting layer and the hole injection layer, between the light-emitting layer and the hole transport layer, or between the light-emitting layer and a layer that performs both hole injection and hole transport simultaneously. Known materials may be used without limitation, but specifically, in one embodiment of this specification, the hole control material may include a compound represented by the chemical formula HT-1, and more specifically, may include an arylamine-based compound containing a carbazole group.

[0240] A hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.

[0241] The above electron control layer is a layer that controls electrons transferred from the electron transport layer to be smoothly injected into the light-emitting layer, and can be formed between the light-emitting layer and the electron injection layer, between the light-emitting layer and the electron transport layer, or between the light-emitting layer and a layer that performs both electron injection and electron transport simultaneously, and known materials can be used without limitation.

[0242] Specifically, in one embodiment of the present specification, the electronic control material may include a triazine derivative compound.

[0243] The electron transport layer described above is a layer that receives electrons from the electron injection layer and transports them to the light-emitting layer. As an electron transport material, it is a material capable of effectively receiving electrons from the cathode and transferring them to the light-emitting layer, and a material with high electron mobility is preferred. Specific examples include the aforementioned compounds or Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; hydroxyflavone-metal complexes, but are not limited to these. The thickness of the electron transport layer may be 1 nm to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage in preventing the electron transport characteristics from degrading, and if it is 50 nm or less, there is an advantage in preventing the driving voltage from rising to improve electron transport due to the thickness of the electron transport layer being too thick.

[0244] In one embodiment of the present invention, the electron transport layer may comprise, but is not limited to, the following compounds.

[0245]

[0246] In one embodiment of the present specification, the electron transport material may include at least one of lithium quinolate (Liq) and a compound of the following chemical formula ET-1.

[0247] [Chemical Formula ET-1]

[0248]

[0249] In the above chemical formula ET-1,

[0250] At least one of Z11 to Z13 is N, and the rest are CH, and

[0251] At least one of Z14 to Z16 is N, and the rest are CH, and

[0252] L701 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0253] Ar701 to Ar704 are the same or different from each other and are each independently substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups, and

[0254] l701 is an integer from 1 to 4, and when l701 is plural, L701 are the same or different from each other.

[0255] According to one embodiment of the present specification, the L701 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0256] According to one embodiment of the present specification, the L701 is a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylene group; or a substituted or unsubstituted naphthylene group.

[0257] According to one embodiment of the present specification, the L701 is a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0258] According to one embodiment of the present specification, the Ar701 to Ar704 are the same or different from each other and are each independently substituted or unsubstituted monocyclic or polycyclic aryl groups having 6 to 30 carbon atoms, or heteroaryl groups having 3 to 30 carbon atoms.

[0259] According to one embodiment of the present specification, Ar701 to Ar704 are substituted or unsubstituted phenyl groups.

[0260] In one embodiment of the present specification, the electron transport material may be a mixture of lithium quinolate (Liq) and a compound of the formula ET-1 in a weight ratio of 1:9 to 9:1, specifically in a weight ratio of 2:8 to 8:2, and more specifically in a weight ratio of 3:7 to 7:3.

[0261] The electron injection layer described above can facilitate the injection of electrons. As an electron injection material, a compound is preferred that has the ability to transport electrons, has an excellent electron injection effect from the cathode, an excellent electron injection effect on the emissive layer or the emissive material, prevents the movement of excitons generated in the emissive layer to the hole injection layer, and also has excellent thin film formation ability. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preolenylidene methane, anthrone, etc., their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but is not limited thereto.

[0262] The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtolato)aluminum, Examples include bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, but are not limited thereto.

[0263] In one embodiment of the present specification, the electron injection material may include at least one of magnesium and lithium fluoride (LiF), and specifically, may include both magnesium and lithium fluoride (LiF).

[0264] In one embodiment of the present specification, a capping layer (CPL) may be deposited on the outer edge of the cathode, and the capping layer serves to maximize the light extraction effect or prevent degradation of the organic light-emitting diode, and may include a capping layer material known in the art. Specifically, the capping layer material may include a compound represented by the following chemical formula CP-1, but is not limited thereto.

[0265] [Chemical Formula CP-1]

[0266]

[0267] In the above chemical formula CP-1,

[0268] L801 to L803 are the same or different from one another, and each is independently a directly bonded, substituted, or unsubstituted arylene group, and

[0269] Ar801 to Ar803 are the same or different from one another, and each is independently hydrogen, deuterium, or a substituted or unsubstituted aryl group, and

[0270] n801 to n803 are integers of 1 or 2, and if n801 to n803 are 2 or more, then 2 or more L801 to L803 are each the same or different from each other.

[0271] In one embodiment of the present specification, L801 to L803 are the same or different from each other and are each independently directly bonded, substituted, or unsubstituted arylene groups having 6 to 20 carbon atoms.

[0272] In one embodiment of the present specification, L801 to L803 are the same or different from each other and are each independently a directly bonded, substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthylene group.

[0273] In one embodiment of the present specification, L801 to L803 are direct couplings.

[0274] In one embodiment of the present specification, the Ar801 to Ar803 are the same or different from each other and are each independently hydrogen, deuterium, or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0275] In one embodiment of the present specification, Ar801 to Ar803 are the same or different from one another and are each independently hydrogen, deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group.

[0276] In one embodiment of the present specification, Ar801 to Ar803 are the same or different from one another and are each independently hydrogen, deuterium, or a substituted or unsubstituted phenyl group.

[0277] In one embodiment of the present specification, Ar801 to Ar803 are the same or different from each other and are each independently hydrogen, deuterium, or a phenyl group.

[0278] The organic light-emitting device according to the present invention may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0279] The above organic light-emitting element may be included in various electronic devices. For example, an electronic device including the above organic light-emitting element may be a light-emitting device, an authentication device, a display device, a lighting device, a mobile terminal, a wearable device, and various other electronic devices. Specifically, the above display device may include a TV, a monitor, a smartphone, a tablet, a laptop display, a smartwatch, a vehicle cluster, a VR / AR display, etc.

[0280] Hereinafter, to specifically explain this specification, examples will be described in detail. However, the embodiments according to this specification may be modified in various different forms, and the scope of this application is not to be interpreted as being limited to the embodiments described below. The embodiments of this application are provided to more completely explain this specification to those with average knowledge in the art.

[0282] <Synthetic Example>

[0283] Synthesis Example 1. Synthesis of Compound 1

[0284]

[0285] Under a nitrogen atmosphere, compound 9-bromo-10-phenylanthracene (20 g, 1 eq.) and compound 1-a (18.9 g, 1.1 eq.) were dissolved in 200 ml of 1,4-dioxane in a round-bottom flask and stirred. Even if not completely dissolved, aq. K2CO3 (16.2 g, dissolved in 70 ml of distilled water, 2 eq.) was added, followed by the addition of bis(tri-tert-butylphosphine)palladium(0)) (0.300 g, 1.0 mol%), and the mixture was heated and stirred for 3 hours. After cooling to room temperature, the organic solvent layer was extracted with distilled water. The organic solvent layer was dried with anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained mixture was separated by column chromatography to obtain compound 1 (20.9 g).

[0286] MS[M+H] + = 503

[0288] Synthesis Example 2. Synthesis of Compound 2

[0289]

[0290] Compound 2 (19.8 g) was obtained by using compound 2-a instead of compound 1-a in the same manner as in Synthesis Example 1.

[0291] MS[M+H]+= 508

[0293] Synthesis Example 3. Synthesis of Compound 3

[0294]

[0295] Compound 3 (16.5 g) was obtained by using compound 2-a instead of compound 1-a and 9-bromo-10-(phenyl-d5)anthracene-1,2,3,4,5,6,7,8-d8 instead of 9-bromo-10-phenylanthracene in the same manner as in Synthesis Example 1.

[0296] MS[M+H]+= 521

[0298] Synthesis Example 4. Synthesis of Compound 4

[0299]

[0300] Compound 4 (24.1 g) was obtained by using compound 4-a instead of compound 1-a and 9-bromo-10-(phenyl-d5)anthracene-1,2,3,4,5,6,7,8-d8 instead of 9-bromo-10-phenylanthracene in the same manner as in Synthesis Example 1.

[0301] MS[M+H]+= 522

[0303] Synthesis Example 5. Synthesis of Compound 5

[0304]

[0305] Compound 5 (28.5 g) was obtained by using compound 5-a instead of compound 1-a in the same manner as in Synthesis Example 1.

[0306] MS[M+H]+= 560

[0308] Synthesis Example 6. Synthesis of Compound 6

[0309]

[0310] Compound 6 (18.2 g) was obtained by using compound 6-a instead of compound 1-a and 2-(10-bromoanthracen-9-yl-1,2,3,4,5,6,7,8-d8)dibenzofuran instead of 9-bromo-10-phenylanthracene in the same manner as in Synthesis Example 1.

[0311] MS[M+H]+= 606

[0313] <Example>

[0314] Example 1.

[0315] A glass substrate coated with a thin film of indium tin oxide (ITO) to a thickness of 150 nm was placed in distilled water containing detergent and cleaned using ultrasound. Fischer Co. products were used as the detergent, and distilled water that had been filtered twice using a Millipore Co. filter was used. After cleaning the ITO for 30 minutes, ultrasonic cleaning was performed for 10 minutes, repeating the process twice with distilled water. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned with solvents of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned using nitrogen plasma for 5 minutes and then transported to a vacuum deposition machine. A hole injection layer was formed by vacuum depositing the following HAT-CN compound to a thickness of 5 nm onto the prepared ITO transparent electrode. Next, HTL-1 was vacuum-deposited to a thickness of 100 nm, and then HTL-2 was vacuum-deposited to a thickness of 10 nm to form a hole transport layer. Next, Compound 1 (host) synthesized in Synthesis Example 1 and Compound BD-A (dopant) (Host compound weight ratio: Dopant compound weight ratio = 95:5) were vacuum-deposited simultaneously to form a 20 nm thick emissive layer. Next, ETL-1 was vacuum-deposited to a thickness of 20 nm to form an electron transport layer. Next, LiF was vacuum-deposited to a thickness of 0.5 nm to form an electron injection layer. Next, aluminum was deposited to a thickness of 100 nm to form a cathode, thereby fabricating an organic light-emitting diode.

[0316] The structure of the compound used in the example is as follows.

[0317]

[0318] Examples 2 to 6 and Comparative Examples 1 to 5

[0319] An organic light-emitting device was fabricated in the same manner as in Example 1, except that the compounds listed in Table 1 below were used instead of Compound 1 as the host of the light-emitting layer in Example 1. At this time, among the structures below, the compound represented by Chemical Formula 1 of the present invention was prepared through the same process as Synthesis Examples 2 to 6 described above.

[0320] The structures of the compounds used in the examples and comparative examples are as follows.

[0321]

[0322] In the organic light-emitting diodes prepared in Examples 1 to 6 and Comparative Examples 1 to 5 above, 10 mA / cm² 2 The driving voltage (Voc) and luminous efficiency (cd / A) were measured at a current density of 20 mA / cm². 2 The time (LT) to reach 97% of the initial brightness at a current density was measured, and the results are shown in Table 1 below.

[0323] Compound (emissive layer host) 10 mA / cm 2 Measured value LT (T97%) Voc Cd / A Example 1 Compound 1 3.10 62.4 200 Example 2 Compound 2 3.08 62.0 216 Example 3 Compound 3 3.10 62.2 220 Example 4 Compound 4 3.02 56.8 245 Example 5 Compound 5 3.03 57.0 230 Example 6 Compound 6 2.98 54.9 225 Comparative Example 1 Compound 7 3.02 56.7 190 Comparative Example 2 Compound 8 3.11 62.3 160 Comparative Example 3 Compound 9 3.10 62.5 180 Comparative Example 4 Compound 10 3.03 56.8 195 Comparative Example 5 Compound 11 3.30 65.5 140

[0325] Examples 1 to 6 using the compound of Formula 1 of the present invention exhibited lower voltage and longer lifespan characteristics than Comparative Examples 1 to 5 not using the compound of Formula 1.

[0326] When comparing Example 1 (applied to Compound 1) and Comparative Example 5 (applied to Compound 11) in which a compound containing Formula A is applied in the present invention, it can be confirmed that Example 1 exhibits low voltage and long life characteristics compared to Comparative Example 5. This is presumed to be a characteristic resulting from the faster mobility of holes and electrons in Compound 1 compared to Compound 11, as naphthoxazole is condensed onto the substituent of Formula A.

[0327] Comparative Example 1 (applied to Compound 7) satisfies the structural formula of the present invention, but since deuterium is not substituted, the lifespan characteristics are inferior to those of the example, and specifically, the effect of voltage and lifespan characteristics according to the position of deuterium substitution can be confirmed through Comparative Examples 2 to 4.

[0328] Specifically, when comparing Example 1 (applied to Compound 1) with Comparative Example 2 (applied to Compound 8), Comparative Example 3 (applied to Compound 9), and Comparative Example 4 (applied to Compound 10), it can be confirmed that Example 1 exhibits long lifespan characteristics compared to Comparative Examples 2 to 4. Through this, it can be confirmed that substituting deuterium at position A of the chemical formula is important for exhibiting long lifespan characteristics of the device compared to substituting deuterium at other positions.

[0329] Although preferred embodiments (hosts) of the present invention have been described above, the present invention is not limited thereto and may be implemented with various modifications within the scope of the claims and the detailed description of the invention, and such modifications also fall within the scope of the invention. Explanation of the symbols

[0331] 1: Substrate 2: Anode 3: Hole injection layer 4: Precision Transport Layer 5: Hole control layer 6: Emissive layer 7: Electronic control layer 8: Electron transport layer 9: Electron injection layer 10: Cathode 11: Capping layer

Claims

Claim 1 Organic compound represented by the following chemical formula 1: [Chemical Formula 1] In the above Chemical Formula 1, R1 to R8 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group; L1 and L2 are the same or different from each other and are each independently a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group; A2 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group; and A1 is a substituent represented by the following Chemical Formula A, [Chemical Formula A] In the above chemical formula A, A3 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and n is an integer from 1 to 5, represents the region connected to L1. Claim 2 The organic compound of claim 1, wherein the formula A is represented by any one of the following formulas A-1 to A-3: [Formula A-1] [Chemical Formula A-2] [Chemical Formula A-3] In the above formulas A-1 to A-3, any one of R9 to R14 is connected to L1, and the substituents among R9 to R14 that are not connected to L1 are the same or different from each other, and each is independently hydrogen or deuterium, and at least one of R9 to R14 is deuterium, and the definition of A3 is the same as the definition in the above formula A. Claim 3 An organic compound according to claim 2, wherein all substituents among R9 to R14 that are not connected to L1 are deuterium. Claim 4 An organic compound according to claim 1, wherein R1 to R8 are the same or different from each other and each independently is hydrogen; or deuterium. Claim 5 An organic compound according to claim 1, wherein A2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms. Claim 6 An organic compound according to claim 1, wherein A2 is a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthrenyl group substituted or unsubstituted with deuterium; a 9,9-dimethylfluorenyl group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; a dibenzothiophen group substituted or unsubstituted with deuterium; or a carbazole group substituted or unsubstituted with deuterium. Claim 7 An organic compound according to claim 1, wherein A3 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms. Claim 8 An organic compound according to claim 1, wherein A3 is a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group substituted or unsubstituted with deuterium; a naphthyl group substituted or unsubstituted with deuterium; a phenanthrenyl group substituted or unsubstituted with deuterium; a 9,9-dimethylfluorenyl group substituted or unsubstituted with deuterium; a benzofuran group substituted or unsubstituted with deuterium; a dibenzofuran group substituted or unsubstituted with deuterium; a benzothiophen group substituted or unsubstituted with deuterium; or a dibenzothiophen group substituted or unsubstituted with deuterium. Claim 9 An organic compound according to claim 1, wherein the chemical formula 1 is represented by any one of the following compounds: . Claim 10 An organic light-emitting device comprising an anode; a cathode; and one or more organic layers provided between the anode and the cathode, wherein one or more of the organic layers comprise a compound according to any one of claims 1 to 9. Claim 11 An organic light-emitting device according to claim 10, wherein the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound. Claim 12 An organic light-emitting device according to claim 10, wherein the organic layer comprises the compound as a host and further comprises a dopant. Claim 13 An organic light-emitting device according to claim 10, wherein the light-emitting layer has a light emission peak within the range of 400 nm to 470 nm. Claim 14 An organic light-emitting device according to claim 11, wherein the organic layer further comprises one or more layers among a hole transport layer, a hole injection layer, an electron blocking layer, a hole injection and transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection layer.

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