Heterocyclic compound and organic light-emitting diode including same

Abstract

The present specification relates to a compound of chemical formula 1, and an organic light-emitting diode including same. The compound can improve efficiency, lower driving voltage, and / or enhance lifespan characteristics in an organic light-emitting diode. In particular, the compound described herein can be used as a material for a light-emitting layer and / or an electron blocking layer. In addition, compared to conventional organic light-emitting elements, the effects of a lower driving voltage, higher efficiency, and / or longer lifespan can be achieved.

Description

Heterocyclic compounds and organic light-emitting devices containing the same

[0001] The present application claims the benefit of the filing dates of Korean Patent Application No. 10-2024-0183835 filed with the Korean Intellectual Property Office on December 11, 2024 and Korean Patent Application No. 10-2025-0193792 filed with the Korean Intellectual Property Office on December 9, 2025, the entire contents of which are incorporated herein.

[0002] This specification relates to heterocyclic compounds and organic light-emitting devices containing the same.

[0003] Generally, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light-emitting devices (OLEDs) utilizing 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 electron blocking layer, an emissive layer, an electron transport layer, an electron injection layer, or a hole blocking layer. In the structure of such an OLED, when a voltage is applied between the two electrodes, holes are injected into the organic layer from the anode and electrons from the cathode. When the injected holes and electrons meet, an exciton is formed, and light is emitted when this exciton returns to the ground state.

[0004] Since the performance of organic light-emitting diodes is significantly affected by the organic material located between the electrodes, the development of new materials for high-performance organic light-emitting diodes is continuously required.

[0005] The present specification provides a heterocyclic compound and an organic light-emitting device comprising the same.

[0006] According to the present specification, a compound represented by the following chemical formula 1 is provided.

[0007] [Chemical Formula 1]

[0008]

[0009] In the above chemical formula 1,

[0010] R1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group, and

[0011] a is an integer from 1 to 7, and b is an integer from 1 to 8, and

[0012] X is represented by the following chemical formula 2, and

[0013] [Chemical Formula 2]

[0014]

[0015] In the above chemical formula 2,

[0016] * is connected to N,

[0017] R3 is hydrogen or deuterium, and

[0018] R4 and R5 combine with each other to form a substituted or unsubstituted five- or six-membered aliphatic hydrocarbon ring, and

[0019] L is a substituted or unsubstituted arylene group having 10 or fewer carbon atoms, and

[0020] Ar is a substituted or unsubstituted aryl group, and

[0021] c is 1 or 2, and

[0022] n is an integer from 0 to 5, and

[0023] m is an integer from 1 to 5, and

[0024] o is 0 or 1, and

[0025] If n is 0 or 1, m+o is 2 or greater.

[0026] According to the present specification, an organic light-emitting device is provided comprising: a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise the compound.

[0027] The compounds described in this specification can be used as materials for the organic layer of an organic light-emitting device, and when used as materials, they can improve efficiency, lower driving voltage, and / or lifespan characteristics in the organic light-emitting device.

[0028] FIGS. 1 and FIGS. 2 illustrate an organic light-emitting element according to one embodiment of the present invention.

[0029] [Explanation of the symbol]

[0030] 1: Substrate

[0031] 2: First electrode

[0032] 3: Hole injection layer

[0033] 4: Precision Transport Layer

[0034] 5: Electromagnetic blocking layer

[0035] 6: Emissive layer

[0036] 7: Hole blocking layer

[0037] 8: Electron injection and transport layer

[0038] 9: Second electrode

[0039] The present specification will be described in more detail below.

[0040] 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.

[0041] 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.

[0042] 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.

[0043] In this 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.

[0044] In this 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.

[0045] In this specification, "or" means an inclusive "or" and not an exclusive "or." For example, condition A or B is satisfied by any one of the following: A is true (or exists) and B is false (or does not exist), A is false (or does not exist) and B is true (or exists), or both A and B are true (or exist).

[0046] In this specification, D means deuterium.

[0047] In this specification, "deuterated," "deuterated substituted," or "deuterated" means that a hydrogen at a substitutable position of a compound is substituted with deuterated hydrogen.

[0048] In this specification, "X% deuterated," "degree of deuteration X%," or "deuterium substitution rate X%" means that X% of the hydrogens at substitutable positions in the structure are replaced with deuterium. For example, if the structure is a carbazole, "25% deuterated" of the carbazole, "degree of deuteration 25%" of the carbazole, or "deuterium substitution rate 25%" of the carbazole means that 2 of the 8 hydrogens at substitutable positions of the carbazole are replaced with or unsubstituted with deuterium.

[0049] In this specification, "adjacent" groups may mean a substituent substituted on an atom directly connected to the atom on which the substituent is substituted, a substituent located closest to the atom on which the substituent is substituted, or another substituent substituted on the atom on which the substituent is substituted. For example, two substituents substituted at the ortho position in a benzene ring and two substituents substituted on the same carbon in an aliphatic ring may be interpreted as adjacent groups.

[0050] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which the present invention pertains. Methods and materials similar or equivalent to those described herein may be used in the practice or testing of embodiments of the present invention, but suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated herein by reference in their entirety, and in the event of conflict, unless a specific passage is not mentioned, the present specification, including definitions, shall prevail. The materials, methods, and embodiments mentioned herein are merely illustrative and are not intended to limit the present invention.

[0051] Examples of substituents in this specification are described below, but are not limited thereto.

[0052] 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.

[0053] In one embodiment of 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; cyano group (-CN); nitro group; hydroxyl group; alkyl group; cycloalkyl group; alkoxy group; phosphine oxide group; aryloxy group; alkyl sulfoxy group; aryl sulfoxy group; alkyl sulfoxy group; aryl sulfoxy group; alkenyl group; silyl group; boron 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.

[0054] In one embodiment of the present specification, the term “substituted or unsubstituted” means that it is substituted with one or more substituents selected from the group consisting of deuterium; alkyl groups; aryl groups; and heterocyclic groups, or that it is substituted with a substituent in which two or more of the exemplified substituents are connected, or that it has no substituents.

[0055] 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.

[0056] Substituents comprising the alkyl group and other alkyl group portions described in this specification include both straight-chain and split-chain forms.

[0057] 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, adamantyl groups, etc. are used, but are not limited thereto.

[0058] In this specification, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms. According to one embodiment, the number of carbon atoms in the aryl group is 6 to 30. According to one embodiment, the number of carbon atoms in the aryl group is 6 to 20. According to one embodiment, the number of carbon atoms in the aryl group is 6 to 18. According to one embodiment, the number of carbon atoms in the aryl group is 6 to 12.

[0059] In the present specification, the aryl group may be a single-ring aryl group or a polycyclic aryl group.

[0060] According to one embodiment, when the aryl group is a single ring, the number of carbon atoms is not particularly limited, but the number of carbon atoms of the single ring aryl group is 6 to 30. According to one embodiment, the number of carbon atoms of the single ring aryl group is 6 to 20. According to one embodiment, the number of carbon atoms of the single ring aryl group is 6 to 18. According to one embodiment, the number of carbon atoms of the single ring aryl group is 6 to 12. The single ring aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.

[0061] According to one embodiment, when the aryl group is polycyclic, the number of carbon atoms is not particularly limited, but the number of carbon atoms of the polycyclic aryl group is 10 to 30. According to one embodiment, the number of carbon atoms of the polycyclic aryl group is 15 to 30. According to one embodiment, the number of carbon atoms of the polycyclic aryl group is 10 to 20. The polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, fluoranthenyl group, triphenylenyl group, etc., but is not limited thereto.

[0062] In this specification, an aryl group of three or more rings is a polycyclic aryl group and refers to an aryl group comprising three or more condensed rings. For example, an aryl group of three or more rings may be an aryl group of three to five rings. The number of carbon atoms in the aryl group of three or more rings is not particularly limited, but the number of carbon atoms in the aryl group of three or more rings is 12 to 30 or 12 to 20. The aryl group of three or more rings may be anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, fluoranthenyl group, triphenylenyl group, etc., but is not limited thereto.

[0063] 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, may include a 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene group, but is not limited thereto.

[0064] 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.

[0065] In this specification, the aryl group among the aryloxy groups may be subject to the description of the aryl group described above.

[0066] 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.

[0067] In this specification, the description of the aryl group described above may be applied to the aryl group among the aryl thioxy group and the aryl sulfoxy group.

[0068] In the present specification, the heterocyclic group is a ring group comprising one or more of the 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, thiophene, furanyl, pyrrole, imidazole, thiazole, oxazole, pyridine, pyrimidine, triazine, triazole, acridine, pyridazine, pyrazine, quinoline, quinazolin, quinoxaline, isoquinoline, indole, indazoline, carbazole, benzoxazole, benzimidazole, benzothiazole, benzocarbazole, benzothiophen, dibenzothiophen, benzofuranyl, phenanthrolinyl, and dibenzofuranyl groups.

[0069] In the present specification, the heterocyclic group may be a single-ring heterocyclic group or a polycyclic heterocyclic group.

[0070] In this specification, the description of the aforementioned heterocyclic group may apply, except that the heteroaryl group is aromatic.

[0071] In this specification, an N-containing heteroaryl group refers to a monocyclic heteroaryl group containing at least one N or a polycyclic heteroaryl group containing at least one N. The number of carbon atoms in the N-containing heteroaryl group is not particularly limited, but is 2 to 30. According to one embodiment, the number of carbon atoms in the N-containing heteroaryl group is 2 to 20. According to one embodiment, the number of carbon atoms in the N-containing heteroaryl group is 5 to 10. Examples of the above N-containing heteroaryl groups may include, but are not limited to, pyrrole groups, imidazole groups, thiazole groups, oxazole groups, pyridine groups, pyrimidine groups, triazine groups, triazole groups, acridine groups, pyridazine groups, pyrazine groups, quinoline groups, quinazolin groups, quinoxaline groups, isoquinoline groups, indole groups, indazoline groups, carbazole groups, benzoxazole groups, benzimidazole groups, benzothiazole groups, benzocarbazole groups, benzofuranyl groups, phenanthrolinyl groups, etc.

[0072] In this specification, the description of the aryl group may apply except that the arylene group is divalent.

[0073] In this specification, the description of the heterocyclic ring may apply except that the divalent heterocyclic ring is divalent.

[0074] In this specification, the description of the heteroaryl group may apply except that the heteroaryl group is divalent.

[0075] In this specification, the meaning of forming a ring by combining with adjacent groups means forming 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 by combining with adjacent groups. The hydrocarbon ring means a ring composed only of carbon and hydrogen atoms. The heteroring means a ring comprising one or more 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.

[0076] In the present specification, in a substituted or unsubstituted ring formed by combining adjacent groups, "ring" means a hydrocarbon ring; or a heteroring.

[0077] The above hydrocarbon ring may be an aromatic, aliphatic, or a condensed ring of aromatic and aliphatic, and may be selected from examples of the above cycloalkyl group or aryl group.

[0078] 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.

[0079] In the present specification, in a ring formed by combining with one another to form a substituted or unsubstituted five- or six-membered aliphatic hydrocarbon ring, examples of the "five- or six-membered aliphatic hydrocarbon ring" include, but are not limited to, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene.

[0080] 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.

[0081] 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.

[0082] 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.

[0083] 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.

[0084] The compound represented by Formula 1 according to the present invention is a compound comprising a ring formed by the condensation of a biscarbazole, an aliphatic ring, and an aromatic ring, and when the compound is used as a material for an organic light-emitting device, it has the characteristics of improving the luminous efficiency of the organic light-emitting device, improving the driving voltage, and improving the lifespan.

[0085] Therefore, when a compound represented by Chemical Formula 1 is applied to an organic light-emitting device, an organic light-emitting device having high efficiency, low voltage, and / or long lifespan characteristics can be obtained.

[0086] The compound represented by Chemical Formula 1 will be described in detail below.

[0087] According to the present specification, a compound represented by the following chemical formula 1 is provided.

[0088] [Chemical Formula 1]

[0089]

[0090] In the above chemical formula 1,

[0091] R1 and R2 are the same or different from each other, and each is independently hydrogen; deuterium; or a substituted or unsubstituted aryl group, and

[0092] a is an integer from 1 to 7, and b is an integer from 1 to 8, and

[0093] X is represented by the following chemical formula 2, and

[0094] [Chemical Formula 2]

[0095]

[0096] In the above chemical formula 2,

[0097] * is connected to N,

[0098] R3 is hydrogen or deuterium, and

[0099] R4 and R5 combine with each other to form a substituted or unsubstituted five- or six-membered aliphatic hydrocarbon ring, and

[0100] L is a substituted or unsubstituted arylene group having 10 or fewer carbon atoms, and

[0101] Ar is a substituted or unsubstituted aryl group, and

[0102] c is 1 or 2, and

[0103] n is an integer from 0 to 5, and

[0104] m is an integer from 1 to 5, and

[0105] o is 0 or 1, and

[0106] If n is 0 or 1, m+o is 2 or greater.

[0107] In the present specification, R1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0108] In the present specification, R1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0109] In the present specification, R1 and R2 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.

[0110] In the present specification, R1 and R2 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.

[0111] In the present specification, R1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; or a substituted or unsubstituted naphthyl group.

[0112] In the present specification, R1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted terphenyl group.

[0113] In the present specification, R1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted phenyl group.

[0114] In this specification, R1 and R2 are the same or different from each other and are each independently hydrogen; or deuterium.

[0115] In the present specification, R1 is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0116] In the present specification, R1 is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0117] In the present specification, R1 is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0118] In the present specification, R1 is hydrogen; deuterium; or a substituted or unsubstituted aryl group of a single ring having 6 to 20 carbon atoms.

[0119] In the present specification, R1 is hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; or a substituted or unsubstituted naphthyl group.

[0120] In the present specification, R1 is hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted terphenyl group.

[0121] In the present specification, R1 is hydrogen; deuterium; and a substituted or unsubstituted phenyl group.

[0122] In the present specification, R1 is hydrogen; or deuterium.

[0123] In the present specification, R2 is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0124] In the present specification, R2 is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0125] In the present specification, R2 is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0126] In the present specification, R2 is hydrogen; deuterium; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms in a single ring.

[0127] In the present specification, R2 is hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; or a substituted or unsubstituted naphthyl group.

[0128] In the present specification, R2 is hydrogen; deuterium; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted terphenyl group.

[0129] In the present specification, R2 is hydrogen; deuterium; or a substituted or unsubstituted phenyl group.

[0130] In the present specification, R2 is hydrogen; or deuterium.

[0131] In the present specification, a is an integer from 1 to 7.

[0132] In the present specification, a is 1.

[0133] In the present specification, a is 2.

[0134] In this specification, a is 3.

[0135] In the present specification, a is 4.

[0136] In this specification, a is 5.

[0137] In this specification, a is 6.

[0138] In this specification, a is 7.

[0139] In the present specification, b is an integer from 1 to 8.

[0140] In the present specification, b is 1.

[0141] In the present specification, b is 2.

[0142] In the present specification, b is 3.

[0143] In the present specification, b is 4.

[0144] In the present specification, b is 5.

[0145] In the present specification, b is 6.

[0146] In the present specification, b is 7.

[0147] In the present specification, b is 8.

[0148] In this specification, R3 is hydrogen or deuterium.

[0149] In this specification, R3 is hydrogen.

[0150] In this specification, R3 is deuterium.

[0151] In the present specification, R4 and R5 are combined with each other to form a substituted or unsubstituted five-membered or six-membered aliphatic hydrocarbon ring.

[0152] In the present specification, R4 and R5 are combined with each other to form a five- or six-membered aliphatic hydrocarbon ring substituted or unsubstituted with an alkyl group.

[0153] In the present specification, the R4 and R5 are combined with each other to form a five- or six-membered aliphatic hydrocarbon ring substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.

[0154] In the present specification, R4 and R5 are combined with each other to form a 5- or 6-membered aliphatic hydrocarbon ring substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

[0155] In the present specification, the R4 and R5 are combined with each other to form a five- or six-membered aliphatic hydrocarbon ring that is substituted or unsubstituted with an alkyl group having 1 to 5 carbon atoms.

[0156] In the present specification, R4 and R5 combine with each other to form substituted or unsubstituted cyclopentane; substituted or unsubstituted cyclopentene; substituted or unsubstituted cyclohexane; or substituted or unsubstituted cyclohexene.

[0157] In the present specification, R4 and R5 combine with each other to form substituted or unsubstituted cyclopentane; or substituted or unsubstituted cyclohexane.

[0158] In the present specification, R4 and R5 combine with each other to form cyclopentane substituted or unsubstituted with an alkyl group; cyclopentene substituted or unsubstituted with an alkyl group; cyclohexane substituted or unsubstituted with an alkyl group; or cyclohexene substituted or unsubstituted with an alkyl group.

[0159] In the present specification, R4 and R5 combine with each other to form cyclopentane substituted or unsubstituted with an alkyl group; or cyclohexane substituted or unsubstituted with an alkyl group.

[0160] In the present specification, R4 and R5 combine with each other to form cyclopentane substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms; cyclopentene substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms; cyclohexane substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms; or cyclohexene substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.

[0161] In the present specification, R4 and R5 combine with each other to form cyclopentane substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms; or cyclohexane substituted or unsubstituted with an alkyl group having 1 to 20 carbon atoms.

[0162] In the present specification, R4 and R5 combine with each other to form cyclopentane substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; cyclopentene substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; cyclohexane substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; or cyclohexene substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

[0163] In the present specification, R4 and R5 combine with each other to form cyclopentane substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms; or cyclohexane substituted or unsubstituted with an alkyl group having 1 to 10 carbon atoms.

[0164] In the present specification, R4 and R5 combine with each other to form cyclopentane substituted or unsubstituted with an alkyl group having 1 to 5 carbon atoms; cyclopentene substituted or unsubstituted with an alkyl group having 1 to 5 carbon atoms; cyclohexane substituted or unsubstituted with an alkyl group having 1 to 5 carbon atoms; or cyclohexene substituted or unsubstituted with an alkyl group having 1 to 5 carbon atoms.

[0165] In the present specification, R4 and R5 combine with each other to form cyclopentane substituted or unsubstituted with an alkyl group having 1 to 5 carbon atoms; or cyclohexane substituted or unsubstituted with an alkyl group having 1 to 5 carbon atoms.

[0166] In the present specification, L is a substituted or unsubstituted arylene group having 10 or fewer carbon atoms.

[0167] In the present specification, L is a substituted or unsubstituted arylene group having 6 to 10 carbon atoms.

[0168] In the present specification, L is a substituted or unsubstituted single-ring arylene group having 10 or fewer carbon atoms.

[0169] In the present specification, L is a substituted or unsubstituted phenylene group.

[0170] In the present specification, L is an arylene group having 10 or fewer carbon atoms that is substituted or unsubstituted with deuterium.

[0171] In the present specification, L is an arylene group having 6 to 10 carbon atoms that is substituted or unsubstituted with deuterium.

[0172] In the present specification, L is a single-ring arylene group having 10 or fewer carbon atoms that is substituted or unsubstituted with deuterium.

[0173] In the present specification, L is a phenylene group substituted or unsubstituted with deuterium.

[0174] In this specification, the Ar is a substituted or unsubstituted aryl group.

[0175] In the present specification, the Ar is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0176] In the present specification, the Ar is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0177] In the present specification, the Ar is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0178] In the present specification, the Ar 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 tetrahydronaphthalene; or a substituted or unsubstituted indan.

[0179] In the present specification, the Ar 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 tetrahydronaphthalene; or a substituted or unsubstituted indan.

[0180] In the present specification, the Ar is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted tetrahydronaphthalene; or a substituted or unsubstituted indan.

[0181] In this specification, the Ar is an aryl group substituted or unsubstituted with deuterium.

[0182] In the present specification, the Ar is an aryl group having 6 to 60 carbon atoms that is substituted or unsubstituted with deuterium.

[0183] In the present specification, the Ar is an aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium.

[0184] In the present specification, the Ar is an aryl group having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium.

[0185] In the present specification, the Ar 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 tetrahydronaphthalene substituted or unsubstituted with deuterium; or an indan substituted or unsubstituted with deuterium.

[0186] In the present specification, the Ar 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 tetrahydronaphthalene substituted or unsubstituted with deuterium; or an indan substituted or unsubstituted with deuterium.

[0187] In the present specification, the Ar 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; tetrahydronaphthalene substituted or unsubstituted with deuterium; or an indan substituted or unsubstituted with deuterium.

[0188] In the present specification, c is 1 or 2.

[0189] In the present specification, c is 1.

[0190] In the present specification, c is 2.

[0191] In the present specification, n is an integer from 0 to 5.

[0192] In the present specification, n is 0.

[0193] In the case where n is 0, it means that L is a direct combination.

[0194] In the present specification, n is 1.

[0195] In the present specification, n is 2.

[0196] In the present specification, n is 3.

[0197] In the present specification, n is 4.

[0198] In the present specification, n is 5.

[0199] In the present specification, m is an integer from 1 to 5.

[0200] In the present specification, m is 1.

[0201] In this specification, m is 2.

[0202] In this specification, m is 3.

[0203] In this specification, m is 4.

[0204] In this specification, m is 5.

[0205] In the case where the above m is an integer greater than or equal to 2, 2 or more It means that it is combined in a continuous sequence.

[0206] In the present specification, o is 0 or 1.

[0207] In this specification, the above o is 0.

[0208] In the present specification, the above o is 1.

[0209] In the present specification, when n is 0 or 1, m+o is 2 or more.

[0210] In the present specification, when n is 0 or 1, m+o is 2.

[0211] In the present specification, when n is 0 or 1, m+o is 3.

[0212] In the present specification, when n is 0 or 1, m+o is 4.

[0213] In the present specification, when n is 0 or 1, m+o is 5.

[0214] In the present specification, when n is 0 or 1, m+o is 6.

[0215] That is, if n is 0 or 1, m is 2 or greater, or o is 1.

[0216] If n is 0 or 1, m is 2 or more.

[0217] If n is 0 or 1, o is 1.

[0218] In one embodiment of the present specification, the formula 1 provides a compound represented by any one of the following formulas 1-1 to 1-4.

[0219] [Chemical Formula 1-1]

[0220]

[0221] [Chemical Formula 1-2]

[0222]

[0223] [Chemical Formula 1-3]

[0224]

[0225] [Chemical Formula 1-4]

[0226]

[0227] In the above chemical formulas 1-1 to 1-4,

[0228] X, R1, R2, a and b are as defined in Chemical Formula 1 above.

[0229] In one embodiment of the present specification, the formula 2 provides a compound represented by the following formula 2-1 or 2-2.

[0230] [Chemical Formula 2-1]

[0231]

[0232] [Chemical Formula 2-2]

[0233]

[0234] In the above chemical formulas 2-1 and 2-2, R41 to R44 are the same or different from each other and are each independently a carbon-1 to 10 alkyl group substituted or unsubstituted with deuterium, and R3, L, Ar, c, n, m and o are as defined in chemical formula 2.

[0235] In the present specification, R41 to R44 are the same or different from each other and are each independently a carbon-1 to 10 alkyl group substituted or unsubstituted with deuterium.

[0236] In the present specification, R41 to R44 are the same or different from each other and are each independently a carbon-1 to 5 alkyl group substituted or unsubstituted with deuterium.

[0237] In the present specification, R41 to R44 are the same or different from each other and are each independently a carbon-1 to 5 alkyl group substituted or unsubstituted with deuterium.

[0238] In the present specification, R41 to R44 are the same or different from one another and are each independently a methyl group substituted or unsubstituted with deuterium; an ethyl group substituted or unsubstituted with deuterium; a propyl group substituted or unsubstituted with deuterium; an isopropyl group substituted or unsubstituted with deuterium; a butyl group substituted or unsubstituted with deuterium; or a pentyl group substituted or unsubstituted with deuterium.

[0239] In the present specification, R41 to R44 are the same or different from each other and are each independently a methyl group substituted or unsubstituted with deuterium; and an ethyl group substituted or unsubstituted with deuterium.

[0240] In the present specification, R41 to R44 are the same or different from each other and are each independently a methyl group substituted or unsubstituted with deuterium.

[0241] In one embodiment of the present specification, at least one of R1 and R2 comprises a substituted or unsubstituted aryl group.

[0242] In the present specification, at least one of R1 and R2 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.

[0243] In the present specification, at least one of R1 and R2 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0244] In the present specification, at least one of R1 and R2 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0245] In the present specification, at least one of R1 and R2 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; or a substituted or unsubstituted phenanthrenyl group.

[0246] In the present specification, at least one of R1 and R2 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted terphenyl group.

[0247] In the present specification, at least one of R1 and R2 is a substituted or unsubstituted phenyl group; or a substituted or unsubstituted biphenyl group.

[0248] In the present specification, at least one of R1 and R2 is a substituted or unsubstituted phenyl group.

[0249] In the present specification, at least one of R1 and R2 is an aryl group having 6 to 60 carbon atoms that is substituted or unsubstituted with deuterium.

[0250] In the present specification, at least one of R1 and R2 is an aryl group having 6 to 30 carbon atoms that is substituted or unsubstituted with deuterium.

[0251] In the present specification, at least one of R1 and R2 is an aryl group having 6 to 20 carbon atoms that is substituted or unsubstituted with deuterium.

[0252] In the present specification, at least one of R1 and R2 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; or a phenanthrenyl group substituted or unsubstituted with deuterium.

[0253] In the present specification, at least one of R1 and R2 is a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; or a terphenyl group substituted or unsubstituted with deuterium.

[0254] In the present specification, at least one of R1 and R2 is a phenyl group substituted or unsubstituted with deuterium; or a biphenyl group substituted or unsubstituted with deuterium.

[0255] In the present specification, at least one of R1 and R2 is a phenyl group substituted or unsubstituted with deuterium.

[0256] In the present specification, the compound represented by the above chemical formula 1 is any one selected from the following structures.

[0257]

[0258] In the above structure, X is represented by the above chemical formula 2.

[0259] In one embodiment of the present specification, a compound is provided in which at least one hydrogen in the structure is substituted with deuterium.

[0260] That is, in one embodiment of the present specification, the compound represented by the chemical formula 1 is a compound having a structure in which one or more deuterium atoms are substituted in any one of the following structures.

[0261]

[0262] In the above structure, X is represented by the above chemical formula 2.

[0263] When the compound represented by Chemical Formula 1 of the present invention contains deuterium, the efficiency and lifespan of the device are improved. Since the bond energy of CD is greater than the bond energy of CH, when hydrogen in the compound is replaced with deuterium, it has a stronger bond energy compared to a compound without deuterium, thereby improving the stability of the compound. Accordingly, when the compound contains deuterium, it prevents a decrease in quantum efficiency caused by a reduction in intermolecular van der Waals forces or collisions due to intermolecular vibrations, and thus improves the lifespan characteristics of the device when the compound is applied to an organic light-emitting diode.

[0264] In one embodiment of the present specification, the compound represented by Chemical Formula 1 comprises at least one deuterium.

[0265] In one embodiment of the present specification, the compound represented by Chemical Formula 1 has a deuterium content of 10% or more.

[0266] In one embodiment of the present specification, the compound represented by Chemical Formula 1 has a deuteriumization rate of 20% or more.

[0267] In one embodiment of the present specification, the compound represented by Chemical Formula 1 has a deuteriumization rate of 30% or more.

[0268] In one embodiment of the present specification, the compound represented by Chemical Formula 1 has a deuteriumization rate of 40% or more.

[0269] In one embodiment of the present specification, the compound represented by Chemical Formula 1 has a deuteriumization rate of 50% or more.

[0270] In one embodiment of the present specification, the compound represented by Chemical Formula 1 has a deuteriumization rate of 60% or more.

[0271] In one embodiment of the present specification, the compound represented by Chemical Formula 1 has a deuteriumization rate of 70% or more.

[0272] In one embodiment of the present specification, the compound represented by Chemical Formula 1 has a deuteriumization rate of 80% or more.

[0273] In one embodiment of the present specification, the compound represented by Chemical Formula 1 has a deuteriumization rate of 90% or more.

[0274] In one embodiment of the present specification, the compound represented by Chemical Formula 1 has a deuteriumization rate of 100%.

[0275] In one embodiment of the present specification, the compound represented by Chemical Formula 1 is any one selected from the following compounds.

[0276]

[0277]

[0278]

[0279] A compound represented by Formula 1 according to one embodiment of this specification can be prepared by the method of the following preparation 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.

[0280] 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.

[0281] In addition, the present specification provides an organic light-emitting device comprising the compound described above.

[0282] In this specification, "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 sub-pixel.

[0283] In this specification, n-type can be any material generally known to be capable of taking electrons from a matrix material (material of an organic layer), but is not limited thereto. That is, n-type can be defined as a material having the characteristic of being able to provide electrons to the LUMO (lowest unoccupied molecular orbital) energy level of the matrix. Conversely, p-type refers to a material that, when a layer is formed solely of p-type material, accepts electrons from the HOMO (highest occupied molecular orbital) energy level of the material located in the adjacent cathode direction, thereby generating holes in that material; or, when an arbitrary matrix is ​​doped with p-type material, accepts electrons from the HOMO of the matrix material and generates holes in the matrix HOMO by the same amount. To achieve this, when a layer is formed solely of p-type material, the closer the HOMO level of the material located in the cathode direction is to the LUMO of the p-type material, the easier it is to steal electrons from the HOMO of the adjacent layer and generate holes in the adjacent layer. Furthermore, when p-type is doped into an arbitrary matrix, the closer the LUMO of the p-type material is to the HOMO of the matrix, the easier it is to steal electrons and generate holes in the matrix.

[0284] The present specification provides an organic light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein one or more of the organic layers comprise a compound of Formula 1.

[0285] The organic layer of the organic light-emitting device of the present specification may be formed as a single layer structure, but may be formed as a multilayer structure in which two or more organic layers are stacked. For example, it may have a structure including a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer, a hole blocking layer, etc. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers.

[0286] According to one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound.

[0287] According to one embodiment of the present specification, the light-emitting layer comprises a host and a dopant, and the host comprises the compound.

[0288] That is, according to one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound as a host of the light-emitting layer.

[0289] According to one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound as an n-type host of the light-emitting layer.

[0290] According to one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound as an n-type phosphorescent host of the light-emitting layer.

[0291] According to one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound as an n-type phosphorescent blue host of the light-emitting layer.

[0292] According to one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound as a p-type host of the light-emitting layer.

[0293] According to one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound as a p-type phosphorescent host of the light-emitting layer.

[0294] According to one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound as a p-type phosphorescent blue host of the light-emitting layer.

[0295] According to one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound as a host and further comprises another host.

[0296] According to one embodiment of the present specification, the organic layer comprises a light-emitting layer, the light-emitting layer comprises the compound as a host, and further comprises the host and a dopant.

[0297] According to one embodiment of the present specification, the organic layer comprises a light-emitting layer, and the light-emitting layer comprises the compound as a first host and further comprises a second host.

[0298] According to one embodiment of the present specification, the first host is a p-type host, and the second host is an n-type host.

[0299] According to one embodiment of the present specification, the first host is a p-type phosphorescent host, and the second host is an n-type phosphorescent host.

[0300] According to one embodiment of the present invention, the second host is a dibenzofuran-based compound.

[0301] According to one embodiment of the present invention, the second host is a dibenzofuran-based compound substituted with a carbazole group and a triazine group.

[0302] According to one embodiment of the present specification, the light-emitting layer comprises a first host and a second host in a weight ratio of 2:8 to 8:2, and the first host is a compound of Formula 1.

[0303] According to one embodiment of the present specification, the light-emitting layer comprises a first host and a second host in a weight ratio of 1:1, and the first host is a compound of Formula 1.

[0304] According to one embodiment of the present specification, the light-emitting layer further comprises a dopant.

[0305] According to one embodiment of the present specification, the light-emitting layer includes a first host and a second host, and further includes a dopant.

[0306] According to one embodiment of the present specification, the dopant is a phosphorescent dopant.

[0307] According to one embodiment of the present specification, the dopant is included in an amount of 1 to 20 parts by weight per 100 parts by weight of the host.

[0308] According to one embodiment of the present specification, the light-emitting layer comprises a dopant, and the dopant comprises a phosphorescent dopant.

[0309] According to one embodiment of the present specification, the organic layer comprises a light-emitting layer, the light-emitting layer comprises a host and a dopant, the host comprises the compound, and the dopant comprises the phosphorescent dopant.

[0310] According to one embodiment of the present specification, the light-emitting layer is a blue light-emitting layer.

[0311] According to one embodiment of the present specification, the light-emitting layer comprises a host and a dopant in a weight ratio of 99:1 to 1:99. Specifically, it comprises a weight ratio of 99:1 to 50:50, and more specifically, a weight ratio of 99:1 to 95:5.

[0312] When the above-mentioned light-emitting layer emits red light, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), and PtOEP(octaethylporphyrin platinum), or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as light-emitting dopants, but are not limited thereto. When the light-emitting layer emits green light, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium) or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) may be used as light-emitting dopants, but are not limited thereto. 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.

[0313] According to one embodiment of the present specification, the dopant is a metal complex compound.

[0314] According to one embodiment of the present specification, the dopant is a platinum complex compound.

[0315] According to one embodiment of the present specification, the dopant is an iridium complex compound.

[0316] According to one embodiment of the present specification, the dopant is the following chemical formula D-1 or D-2, but is not limited thereto.

[0317] [Chemical Formula D-1]

[0318]

[0319] [Chemical Formula D-2]

[0320]

[0321] In the above chemical formulas D-1 and D-2,

[0322] M is a transition metal, and

[0323] A1, A3, A5, A6, K1, K2 and K3 are the same or different from one another and are each independently directly bonded; O; S; a divalent ester group; a substituted or unsubstituted alkylene group; a substituted or unsubstituted divalent alkenyl group; a substituted or unsubstituted divalent allyl group; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0324] A2 and A4 are the same or different from each other and are each independently directly bonded; N; a substituted or unsubstituted trivalent alkylene group; a substituted or unsubstituted trivalent aryl group; or a substituted or unsubstituted trivalent heteroaryl group, and

[0325] n is 1 or 2, and when n is 2, the structures within the parentheses are the same or different.

[0326] According to one embodiment of the present specification, M is iridium or platinum.

[0327] According to one embodiment of the present specification, the dopant may be selected from the following structural formulas, but is not limited thereto.

[0328]

[0329]

[0330]

[0331]

[0332] According to one embodiment of the present specification, the organic layer further comprises one or more layers among a hole injection layer, a hole transport layer, a hole injection and transport layer, an electron blocking layer, a light-emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron injection and transport layer.

[0333] According to one embodiment of the present specification, the organic light-emitting device further comprises one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer.

[0334] According to one embodiment of the present specification, the organic light-emitting element comprises: a first electrode; a second electrode provided opposite to the first electrode; a light-emitting layer provided between the first electrode and the second electrode; and two or more organic layers provided between the light-emitting layer and the first electrode, or between the light-emitting layer and the second electrode.

[0335] According to one embodiment of the present specification, two or more organic layers may be selected from the group consisting of a hole injection layer, a hole transport layer, a hole injection and transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, an electron injection and transport layer, a hole blocking layer, and an electron blocking layer.

[0336] According to one embodiment of the present specification, two or more hole transport layers are included between the light-emitting layer and the first electrode. The two or more hole transport layers may include materials that are the same or different from each other.

[0337] According to one embodiment of the present specification, the organic layer comprises a hole injection layer, a hole transport layer, a hole injection and transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, the hole injection and transport layer, or the electron blocking layer comprises the compound.

[0338] According to one embodiment of the present specification, the first electrode is an anode or a cathode.

[0339] According to one embodiment of the present specification, the second electrode is a cathode or an anode.

[0340] According to 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.

[0341] According to 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.

[0342] For example, the structure of an organic light-emitting device according to one embodiment of the present specification is illustrated in FIGS. 1 and 2. FIGS. 1 and 2 illustrate an organic light-emitting device and are not limited thereto.

[0343] FIG. 1 illustrates the structure of an organic light-emitting device in which a first electrode (2), a light-emitting layer (6), and a second electrode (9) are sequentially stacked on a substrate (1). The compound is included in the light-emitting layer (6).

[0344] FIG. 2 illustrates the structure of an organic light-emitting device in which a first electrode (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 second electrode (9) are sequentially stacked on a substrate (1). The compound is included in the light-emitting layer (6) and / or the electron blocking layer (5).

[0345] The organic light-emitting device of the present specification may be manufactured using materials and methods known in the art, except that the hole injection layer, hole transport layer, hole injection and transport layer, electron blocking layer and / or light-emitting layer comprises a compound of Formula 1.

[0346] 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.

[0347] For example, the organic light-emitting device of the present specification can be manufactured by sequentially stacking a first electrode, an organic layer, and a second electrode on a substrate. At this time, the device can be manufactured by forming an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a physical vapor deposition (PVD) method such as sputtering or electron beam evaporation, forming an organic layer including a hole injection layer, a hole transport layer, a light-emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon. In addition to such a method, the organic light-emitting device can be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0348] In addition, the compound of Chemical Formula 1 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, doctor blading, inkjet printing, screen printing, spraying, roll coating, etc., but is not limited thereto.

[0349] As for the anode material, a material with a high work function is generally preferred to facilitate hole injection into the organic layer. Examples 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 metal and oxide such as ZnO:Al or SnO2:Sb; conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline, but are not limited thereto.

[0350] The above cathode material is preferably a material with a small work function to facilitate electron injection into an organic layer. Examples 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 thereto.

[0351] The above-described light-emitting layer may include a host material and a dopant material. In the case where an organic light-emitting device according to one embodiment of the present specification includes an additional light-emitting layer other than the light-emitting layer comprising Chemical Formula 1, the host material may be a condensed aromatic ring derivative or a heterocyclic compound, etc.

[0352] Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic containing compounds include dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc., but are not limited thereto.

[0353] The above dopant materials include aromatic amine derivatives, styramine compounds, boron complexes, fluoranthene compounds, metal complexes, etc. Specifically, aromatic amine derivatives are condensed aromatic ring derivatives having substituted or unsubstituted arylamine groups, such as pyrene, anthracene, chrysene, and periplantene having arylamine groups. In addition, styramine compounds are compounds in which at least one arylvinyl group is substituted on a substituted or unsubstituted arylamine, wherein one or more substituents selected from the group consisting of aryl groups, silyl groups, alkyl groups, cycloalkyl groups, and arylamine groups are substituted or unsubstituted. Specifically, styramine, styryldiamine, styryltriamine, styryltetraamine, etc. are examples, but are not limited thereto. In addition, metal complexes include iridium complexes, platinum complexes, etc., but are not limited thereto.

[0354] The hole injection layer described above is a layer that receives holes from an electrode. It is desirable for the hole injection material to have the ability to transport holes, thereby having an excellent hole receiving effect from the anode and an excellent hole injection effect on the emitting layer or emitting material. In addition, it is desirable for the material to have an excellent ability to prevent the movement of excitons generated in the emitting layer to the electron injection layer or electron injection material. In addition, it is desirable for the material to have an excellent thin film formation ability. Furthermore, it is desirable for the HOMO (highest occupied molecular orbital) of the hole injection material to be 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, metal porphyrins, oligothiophenes, arylamine-based organic materials; hexanitrile-hexaazatriphenylene-based organic materials; quinacridone-based organic materials; perylene-based organic materials; and polythiophene-based conductive polymers such as anthraquinone and polyaniline.

[0355] According to one embodiment of the present specification, the hole injection layer comprises a compound represented by the following chemical formula HI-1, but is not limited thereto.

[0356] [Chemical Formula HI-1]

[0357]

[0358] In the above chemical formula HI-1,

[0359] 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; and combinations thereof, or are combined with adjacent groups to form a substituted or unsubstituted ring, and

[0360] 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,

[0361] 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.

[0362] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof.

[0363] According to one embodiment of the present specification, the R317 is any one selected from the group consisting of a substituted or unsubstituted carbazole group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted triphenylene group; and combinations thereof.

[0364] According to one embodiment of the present specification, R315 and R316 are the same or different from each other and are each independently substituted or unsubstituted aryl groups, or they combine with adjacent groups to form an aromatic hydrocarbon ring substituted with an aryl group or an alkyl group.

[0365] According to one embodiment of the present specification, R315 and R316 are the same or different from each other and are each independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, or are combined with adjacent groups to form a fluorene group substituted or unsubstituted with a phenyl group or a methyl group.

[0366] According to one embodiment of the present specification, the chemical formula HI-1 is represented by any one of the following compounds.

[0367]

[0368] According to one embodiment of the present specification, the hole injection layer comprises a compound represented by the following chemical formula HI-2, but is not limited thereto.

[0369] [Chemical Formula HI-2]

[0370]

[0371] In the above chemical formula HI-2,

[0372] R401 to R403 are the same or the same as above, and each is independently a halogen group, and

[0373] r401 to r403 are 4.

[0374] According to one embodiment of the present specification, R401 to R403 are F.

[0375] According to one embodiment of the present specification, the chemical formula HI-2 is represented by the following compound.

[0376]

[0377] According to one embodiment of the present specification, the hole injection layer comprises the chemical formulas HI-1 and HI-2.

[0378] According to one embodiment of the present specification, the hole injection layer comprises the chemical formulas HI-1 and HI-2 in a weight ratio of 1:99 to 99:1.

[0379] The hole transport layer described above is a layer that receives holes from the hole injection layer and transports them to the emissive layer. As for the hole transport material, a material capable of receiving holes from the anode or the hole injection layer and transferring them to the emissive layer is preferably a material with high mobility for holes. Specific examples include, but are not limited to, arylamine-based organic materials, conductive polymers, and block copolymers containing both conjugated and non-conjugated portions.

[0380] According to one embodiment of the present specification, the hole transport layer comprises a compound represented by the chemical formula HI-1, but is not limited thereto.

[0381] According to one embodiment of the present specification, the hole injection and transport layer is a layer that transports holes to the light-emitting layer. Materials exemplified in the hole transport layer and hole injection layer may be used, but are not limited thereto.

[0382] 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 for the 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, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The electron transport layer can be used with any desired cathode material as in the prior art. In particular, a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically, examples include cesium, barium, calcium, ytterbium, and samarium, each followed by an aluminum layer or a silver layer.

[0383] The electron injection layer is a layer that receives electrons from an electrode. It is desirable for the electron injection material to have excellent electron transport ability, an electron reception effect from the second electrode, and an excellent electron injection effect on the emitting layer or emitting material. In addition, it is desirable for the material to prevent excitons generated in the emitting layer from moving to the hole injection layer and to have excellent thin film formation ability. Specifically, the electron injection layer material includes, but is not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preolenylidene methane, anthrone, etc., derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives.

[0384] 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, bis(2-methyl-8-quinolinato)(2-naphtolato)gallium, etc., are included but are not limited thereto.

[0385] According to one embodiment of the present specification, the electron injection and transport layer is a layer that transports electrons to the light-emitting layer. The materials exemplified in the electron transport layer and the electron injection layer may be used, but are not limited thereto.

[0386] According to one embodiment of the present specification, the electron injection and transport layer comprises a compound represented by the following chemical formula ET-1, but is not limited thereto.

[0387] [Chemical Formula ET-1]

[0388]

[0389] In the above chemical formula ET-1,

[0390] At least one of Z11 to Z13 is N, and the rest are CH, and

[0391] At least one of Z21 to Z23 is N, and the rest are CH, and

[0392] L601 and L602 are the same or different from each other, and each is independently a directly bonded; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group, and

[0393] Ar601 to Ar604 are the same or different from one another and are each independently substituted or unsubstituted aryl groups; or substituted or unsubstituted heteroaryl groups.

[0394] According to one embodiment of the present specification, L601 and L602 are the same or different from each other and are each independently substituted or unsubstituted monocyclic or polycyclic arylene groups having 6 to 30 carbon atoms.

[0395] According to one embodiment of the present specification, L601 and L602 are phenylene groups.

[0396] According to one embodiment of the present specification, the Ar601 to Ar604 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.

[0397] According to one embodiment of the present specification, Ar601 to Ar604 are phenyl groups or biphenyl groups.

[0398] According to one embodiment of the present specification, the chemical formula ET-1 is represented by the following compound.

[0399]

[0400] According to one embodiment of the present specification, the electron injection and transport layer may further comprise a metal complex compound. The metal complex compound is as described above.

[0401] The above electron blocking layer is a layer capable of improving the lifespan and efficiency of the device by preventing electrons injected from the electron injection layer from passing through the emitting layer and entering the hole injection layer. If the above electron blocking layer includes an additional electron blocking layer in addition to the electron blocking layer comprising the compound of Formula 1 according to one embodiment of the present specification, known materials may be used without limitation, and materials exemplified in the description of the hole injection layer may be used, but are not limited thereto. The above electron blocking layer may be formed between the emitting layer and the hole transport layer, between the emitting layer and the hole injection layer, or between the emitting layer and a layer that performs both hole injection and hole transport simultaneously.

[0402] The hole blocking layer described above is a layer that prevents holes from reaching the cathode and can generally be formed under the same conditions as the electron injection layer. Specifically, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, aluminum complexes, etc. are used, but are not limited thereto.

[0403] According to one embodiment of the present specification, when the organic light-emitting element includes a hole blocking layer in addition to a hole blocking layer comprising a compound of Formula 1, the material exemplified in the hole blocking layer may be used, but is not limited thereto.

[0404] For example, the hole blocking layer comprises a compound represented by the following chemical formula HB-1, but is not limited thereto.

[0405] [Chemical Formula HB-1]

[0406]

[0407] In the above HB-1,

[0408] At least one of Q1 to Q3 is N, and the rest are CH, and

[0409] L701 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group.

[0410] T1 to T3 are the same or different from one another and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0411] According to one embodiment of the present specification, Q1 to Q3 are N.

[0412] According to one embodiment of the present specification, the L701 is a directly bonded; or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.

[0413] According to one embodiment of the present specification, the L701 is a direct bond; or an arylene group.

[0414] According to one embodiment of the present specification, the L701 is a direct bond; or an arylene group having 6 to 30 carbon atoms.

[0415] According to one embodiment of the present specification, the L701 is a direct bond; or a phenylene group.

[0416] According to one embodiment of the present specification, T1 to T3 are the same or different from one another and are each independently substituted or unsubstituted heteroaryl groups.

[0417] According to one embodiment of the present specification, T1 to T3 are the same or different from each other and are each independently substituted or unsubstituted monocyclic or polycyclic heteroaryl groups having 6 to 30 carbon atoms.

[0418] According to one embodiment of the present specification, T1 to T3 are the same or different from each other and are each independently heteroaryl groups.

[0419] According to one embodiment of the present specification, T1 to T3 are the same or different from each other and are each independently a monocyclic or polycyclic heteroaryl group having 6 to 30 carbon atoms.

[0420] According to one embodiment of the present specification, T1 to T3 are carbazole groups.

[0421] According to one embodiment of the present specification, the formula HB-1 may include the following compounds, but is not limited thereto.

[0422]

[0423] According to one embodiment of the present specification, the formula HB-1 may be used as a first host material of the light-emitting layer.

[0424] According to one embodiment of the present specification, the formula HB-1 may be used as a second host material of the light-emitting layer.

[0425] The organic light-emitting device according to the present specification may be a front-emitting type, a back-emitting type, or a double-sided emitting type depending on the material used.

[0426] The organic light-emitting element according to the present specification may be included in and used in various electronic devices. For example, the electronic device may be a light-emitting device, an authentication device, a display device, a lighting device, a mobile terminal, a wearable device, etc. Specifically, the display device may include, but is not limited to, a TV, a monitor, a smartphone, a tablet, a laptop display, lighting, a smartwatch, a vehicle cluster, a VR / AR display, etc.

[0427] Hereinafter, in order to specifically explain the present specification, examples and comparative examples will be described in detail. However, the examples and comparative examples according to the present specification may be modified in various different forms, and the scope of the present specification is not to be interpreted as being limited to the examples and comparative examples described below. The examples and comparative examples of the present specification are provided to more completely explain the present specification to those with average knowledge in the art.

[0428] [Preparation Example]

[0429] Preparation Example 1. Synthesis of Compound K1

[0430]

[0431] Under a nitrogen atmosphere, 25 g of 9H-3,9'-bicarbazole-1,1',2,2',3',4,4',5,5',6,6',7,7',8,8'-d15, 25.2 g of 6-(4-bromophenyl-2,3,5,6-d4)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3, 0.4 g of [bis(tri-tert-butylphosphine)palladium(0)], 18 g of sodium-tert-butoxide, and 600 mL of xylene were added, heated under reflux, and stirred for 8 hours. After the reaction was finished, the reaction mixture was aliquoted, treated with MgSO4 (anhydrous), and filtered. The filtered solution was recrystallized to prepare the compound K1.

[0432] (27g, yield 61%, Mass [M+]=617).

[0433] Preparation Example 2. Synthesis of Compound K2

[0434]

[0435] Compound K2 was prepared using the same method as in Preparation Example 1, except that 25.2g of 6-(3-bromophenyl-2,4,5,6-d4)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3 was used instead of 25.2g of 6-(3-bromophenyl-2,4,5,6-d4)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3.

[0436] (23g, yield 52%, Mass [M+]=617).

[0437] Preparation Example 3. Synthesis of Compound K3

[0438]

[0439] Compound K3 was prepared using the same method as in Preparation Example 1, except that 31g of 6-(3'-bromo-[1,1'-biphenyl]-3-yl-2,2',4,4',5,5',6,6'-d8)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3 was used instead of 25.2g of 6-(4-bromophenyl-2,3,5,6-d4)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3.

[0440] (28g, Yield 56%, Mass [M+]=698).

[0441] Preparation Example 4. Synthesis of Compound K4

[0442]

[0443] Compound K4 was prepared using the same method as in Preparation Example 1, except that 31g of 6-(4'-bromo-[1,1'-biphenyl]-3-yl-2,2',3',4,5,5',6,6'-d8)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3 was used instead of 25.2g of 6-(4-bromophenyl-2,3,5,6-d4)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3.

[0444] (27g, Yield 54%, Mass [M+]=698)

[0445] Preparation Example 5. Synthesis of Compound K5

[0446]

[0447] Compound K5 was prepared using the same method as in Preparation Example 1, except that 36.7 g of 6-(3''-bromo-[1,1':3',1''-terphenyl]-3-yl-2,2',2'',4,4',4'',5,5',5'',6,6',6''-d12)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3 was used instead of 25.2 g of 6-(3''-bromo-[1,1':3',1''-terphenyl]-3-yl-2,2',2'',4,4',4'',5,5',5'',6,6',6''-d12)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3.

[0448] (29g, Yield 52%, Mass [M+]=778)

[0449] Preparation Example 6. Synthesis of Compound K6

[0450]

[0451] Compound K6 was prepared using the same method as in Preparation Example 1, except that 33g of 3-bromo-5,5,5',5',8,8,8',8'-octamethyl-5,5',6',7,7',8,8'-octahydro-1,2'-binaphthalene-1',2,3',4,4'-d5 was used instead of 25.2g of 6-(4-bromophenyl-2,3,5,6-d4)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3.

[0452] (25g, Yield 48%, Mass [M+]=726)

[0453] Preparation Example 7. Synthesis of Compound K7

[0454]

[0455] Compound K7 was prepared using the same method as the preparation method of Preparation Example 3 above, except that 25g of 9H-2,9'-bicarbazole-1,1',2,2',3',4,4',5,5',6,6',7,7',8,8'-d15 was used instead of 25g of 9H-3,9'-bicarbazole-1,1',2',3,3',4,4',5,5',6,6',7,7',8,8'-d15.

[0456] (27g, Yield 54%, Mass [M+]=698)

[0457] Preparation Example 8. Synthesis of Compound K8

[0458]

[0459] Compound K8 was prepared using the same method as the preparation method of Preparation Example 3, except that 25g of 9H-4,9'-bicarbazole-1,1',2,2',3',4,4',5,5',6,6',7,7',8,8'-d15 was used instead of 25g of 9H-3,9'-bicarbazole-1,1',2,2',3,3',4',5,5',6,6',7,7',8,8'-d15.

[0460] (29g, Yield 58%, Mass [M+]=698)

[0461] Preparation Example 9. Synthesis of Compound K9

[0462]

[0463] Compound K9 was prepared using the same method as the preparation method of Preparation Example 1, except that 25g of 9H-3,9'-bicarbazole-1,1',2,2',3',4,4',5,5',6,6',7,7',8,8'-d15 was used instead of 25g of 9H-3,9'-bicarbazole, and 34.1g of 3-bromo-5,5,5',5',8,8,8',8'-octamethyl-5,5',6,6',7,7',8,8'-octahydro-1,2'-binaphthalene was used instead of 25.2g of 6-(4-bromophenyl-2,3,5,6-d4)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene-5,7,8-d3.

[0464] (31.5g, yield 59%, Mass [M+]=705).

[0465] [Example]

[0466] Example 1

[0467] A glass substrate coated with an 800 Å thin film of indium tin oxide (ITO) was placed in distilled water containing dissolved detergent and cleaned using ultrasound. Fischer Co. detergent was used, and distilled water that had been filtered twice using a Millerpore Co. filter was used. After cleaning the ITO for 30 minutes, the ultrasonic cleaning process was repeated twice with distilled water for 10 minutes. After the distilled water cleaning was completed, the substrate was ultrasonically cleaned using isopropyl alcohol, acetone, and methanol as solvents, dried, and then transported to a plasma cleaner. Additionally, the substrate was cleaned using oxygen plasma for 5 minutes and then transported to a vacuum deposition machine.

[0468] A hole injection layer was formed on the prepared ITO transparent electrode by thermal vacuum deposition of compounds HT1 and HI1 in a ratio of 95:5 (molar ratio) to a thickness of 100 Å. A hole transport layer was formed by vacuum deposition of a compound represented by the chemical formula HT1 (300 Å) on the hole injection layer. Subsequently, an electron blocking layer was formed by vacuum deposition of the compound of Preparation Example 1 (p-type) to a film thickness of 50 Å on the hole transport layer. Subsequently, an emitting layer was formed by vacuum deposition of a compound mixed in a 1:1 ratio of the chemical formula BH (n-type) and the compound K1 (p-type) synthesized in Preparation Example 1 as the host of the emitting layer, and a compound represented by the chemical formula BD as the dopant of the emitting layer, in a weight ratio of 70:30 on the electron blocking layer. A hole blocking layer was formed by vacuum deposition of BH (n-type) to a film thickness of 50 Å on the emitting layer. Next, a compound represented by the chemical formula ET1 and a compound represented by the chemical formula LiQ were vacuum-deposited in a weight ratio of 1:1 on the hole-blocking layer to form an electron injection and transport layer with a thickness of 300 Å. A cathode was formed by sequentially depositing lithium fluoride (LiF) with a thickness of 10 Å and aluminum with a thickness of 800 Å on the electron injection and transport layer.

[0469]

[0470] In the above process, the deposition rate of the organic material was maintained at 0.4–0.7 Å / sec, while the deposition rates for the cathode lithium fluoride and aluminum were maintained at 0.3 Å / sec and 2 Å / sec, respectively, and the vacuum level during deposition was 2 × 10⁻¹⁰ -7 ~ 5 x 10 -6 An organic light-emitting diode was fabricated by maintaining torr.

[0471] Examples 2 to 9, and Comparative Examples 1 to 4

[0472] An organic light-emitting device was fabricated in the same manner as in Example 1, except that the compound listed in Table 1 below was used instead of the compound K1 as the host of the light-emitting layer in Example 1.

[0473]

[0474]

[0475] When current was applied to the organic light-emitting diodes fabricated in Examples 1 to 9 and Comparative Examples 1 to 4, the voltage, efficiency, and lifetime were measured (based on 1500 nit), and the results are shown in Table 1 below. Lifetime T90 refers to the time required for the brightness to decrease to 90% from the initial brightness (1500 nit).

[0476] Classification Host Compound Electron Blocking Layer Compound Voltage (V) @ 10 mA / cm 2 Luminous Efficiency (EQE) Lifetime, T90(h) Example 1 Compound K1 Compound K13.4225.9210 Example 2 Compound K2 Compound K13.4125.8212 Example 3 Compound K3 Compound K13.4425.9213 Example 4 Compound K4 Compound K13.4325.7215 Example 5 Compound K5 Compound K13.4625.8211 Example 6 Compound K6 Compound K13.4625.7211 Example 7 Compound K7 Compound K13.5224.5201 Example 8 Compound K8 Compound K13.5124.7200 Example 9 Compound K9 Compound K13.4625.6195 Comparative Example 1 CM1 Compound K14.9316.276 Comparative Example 2 CM2 Compound K13.9122.1109 Comparative Example 3 CM3 Compound K14.3215.457 Comparative Example 4 CM4 Compound K14.3115.680

[0477] As described in Table 1 above, the compound of Formula 1 according to the present specification can be used as a host for the light-emitting layer of an organic light-emitting device. Formula 1 according to one embodiment of the present specification is a compound comprising a ring formed by the condensation of a biscarbazole, an aliphatic ring, and an aromatic ring. When the above compound is used as a material for an organic light-emitting device, it has the characteristics of improving the luminous efficiency of the organic light-emitting device, improving the driving voltage, and improving the lifespan. A compound satisfying the conditions in which Ar of Formula 2 according to one embodiment of the present specification is substituted with deuterium, and when n is 0 or 1 and m+o is 2 or more, the binding energy increases, thereby increasing the stability of the compound, and an organic light-emitting device containing the same has increased stability, improved efficiency and lifespan, and a reduction in voltage.

[0478] Specifically, it can be seen that an organic light-emitting device comprising Formula 1 of the present specification has superior driving voltage, efficiency, and lifespan compared to Comparative Example 1, which comprises a compound in which the substituent corresponding to the position of Ar in the present specification is an aryl group substituted with an amine group, and Comparative Examples 2 and 3, which comprise a compound in which m + o is less than 2 when n is 0 or 1.

[0479] In addition, the compound of Comparative Example 4 is substituted with deuterium in the compound of Comparative Example 3, but since n=0 and m+o is less than 2, the organic light-emitting device containing Chemical Formula 1 of the present specification has superior driving voltage, efficiency, and lifespan compared to Comparative Example 4.

Claims

1. Compound represented by the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, R1 and R2 are the same or different from each other and are each independently hydrogen; deuterium; or a substituted or unsubstituted aryl group, and a is an integer from 1 to 7, and b is an integer from 1 to 8, and X is represented by the following chemical formula 2, and [Chemical Formula 2] In the above chemical formula 2, * is connected to N, R3 is hydrogen or deuterium, and R4 and R5 combine with each other to form a substituted or unsubstituted five- or six-membered aliphatic hydrocarbon ring, and L is a substituted or unsubstituted arylene group having 10 or fewer carbon atoms, and Ar is a substituted or unsubstituted aryl group, and c is 1 or 2, and n is an integer from 0 to 5, and m is an integer from 1 to 5, and o is 0 or 1, and If n is 0 or 1, m+o is 2 or greater.

2. In Claim 1, The above chemical formula 1 is a compound represented by any one of the following chemical formulas 1-1 to 1-4: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] In the above chemical formulas 1-1 to 1-4, X, R1, R2, a and b are as defined in Chemical Formula 1 above.

3. In Claim 1, Compound, wherein the above chemical formula 2 is represented by the following chemical formula 2-1 or chemical formula 2-2: [Chemical Formula 2-1] [Chemical Formula 2-2] In the above chemical formulas 2-1 and 2-2, R41 to R44 are the same or different from each other and are each independently a carbon-1 to 10 alkyl group substituted or unsubstituted with deuterium, and R3, L, Ar, c, n, m, and o are as defined in Chemical Formula 2.

4. In Claim 1, A compound in which L is a phenylene group substituted or unsubstituted with deuterium.

5. In Claim 1, The above Ar is a compound having 6 to 30 carbon atoms, substituted or unsubstituted with deuterium.

6. In Claim 1, A compound in which at least one of the above R1 and R2 is a substituted or unsubstituted aryl group.

7. In Claim 1, The above chemical formula 1 is a compound comprising at least one deuterium.

8. In Claim 1, The compound represented by the above chemical formula 1 is a compound selected from any one of the following structures: In the above structure, X is represented by the above chemical formula 2.

9. In Claim 1, A compound represented by the above chemical formula 1, which has a structure in which one or more deuterium atoms are substituted in any one of the following structures: In the above structure, X is represented by the above chemical formula 2.

10. In Claim 1, A compound represented by the above chemical formula 1 is a compound selected from any one of the following compounds: .

11. An organic light-emitting device comprising a first electrode; a second electrode; and one or more organic layers provided between the first electrode and the second electrode, An organic light-emitting device comprising at least one layer of the above organic layer, the compound of any one of claims 1 to 10.

12. In Claim 11, The above organic layer includes a light-emitting layer, and The above-mentioned light-emitting layer comprises the above-mentioned compound, forming an organic light-emitting device.

13. In Claim 12, The above-mentioned light-emitting layer includes a host and a dopant, and The above host is an organic light-emitting device comprising the above compound.

14. In Claim 11, An organic light-emitting device, wherein the organic layer comprises a hole injection layer, a hole transport layer, a hole injection and transport layer, or an electron blocking layer, and the hole injection layer, the hole transport layer, the hole injection and transport layer, or the electron blocking layer comprises the compound.

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