Compound and organic light-emitting element comprising same

Abstract

The present specification relates to a compound of chemical formula 1, and an organic light-emitting element comprising the compound. The compound described in the present specification can be used as a material for an organic material layer of an organic light-emitting element. The compound, according to at least one embodiment of the present specification, can improve efficiency, lower driving voltage, and / or enhance lifetime characteristics of the organic light-emitting element. In particular, the compound described in the present specification can be used as a material for a light-emitting layer. In addition, compared to conventional organic light-emitting elements, the effects of a lower driving voltage, higher efficiency, and / or longer lifetime can be achieved.

Description

Compound and organic light-emitting device containing the same

[0001] This application claims the benefit of the filing dates of Korean Patent Application No. 10-2024-0073311, filed with the Korean Intellectual Property Office on June 4, 2024, Korean Patent Application No. 10-2024-0073306, filed with the Korean Intellectual Property Office on June 4, 2024, and Korean Patent Application No. 10-2025-0071909, filed with the Korean Intellectual Property Office on June 2, 2025, the entire contents of which are incorporated herein by reference.

[0002] The present specification relates to a compound and an organic light-emitting device comprising the same.

[0003] In this specification, an organic light-emitting device is a light-emitting device using an organic semiconductor material, and requires the exchange of holes and / or electrons between an electrode and the organic semiconductor material. Organic light-emitting devices can be broadly divided into two types according to their operating principles. First, a light-emitting device is a type in which excitons are formed in an organic layer by photons that enter the device from an external light source, these excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes and used as a current source (voltage source). Second, a light-emitting device is a type in which holes and / or electrons are injected into an organic semiconductor material layer forming an interface with the electrodes by applying voltage or current to two or more electrodes, and is operated by the injected electrons and holes.

[0004] In general, organic light emitting phenomenon refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic light emitting devices that utilize the organic light emitting phenomenon typically have a structure that includes an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure composed of different materials to increase the efficiency and stability of the organic light emitting device, and can be composed of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer. In the structure of such an organic light emitting device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons are injected from the cathode into the organic layer. When the injected holes and electrons meet, excitons are formed, and when these excitons fall back to the ground state, light is emitted. Such organic light emitting devices are known to have characteristics such as self-luminescence, high brightness, high efficiency, low operating voltage, wide viewing angle, and high contrast.

[0005] Materials used as organic layers in organic light-emitting devices can be classified according to their function into light-emitting materials and charge-transport materials, such as hole-injecting materials, hole-transporting materials, electron-blocking materials, electron-transporting materials, and electron-injecting materials. Light-emitting materials include blue, green, and red light-emitting materials according to their emission color, as well as yellow and orange light-emitting materials required to realize better natural colors.

[0006] Furthermore, a host / dopant system can be used as a light-emitting material to enhance color purity and luminescence efficiency through energy transfer. This principle is achieved by mixing a small amount of a dopant with a smaller energy band gap and superior luminescence efficiency than the host, which primarily constitutes the light-emitting layer, into the light-emitting layer. This allows excitons generated in the host to be transported to the dopant, resulting in high-efficiency light emission. Since the wavelength of the host shifts to that of the dopant, light of a desired wavelength can be obtained depending on the type of dopant used.

[0007] In order to fully demonstrate the excellent characteristics of the aforementioned organic light-emitting device, the materials forming the organic layer within the device, such as hole injection materials, hole transport materials, luminescent materials, electron blocking materials, electron transport materials, and electron injection materials, must be supported by stable and efficient materials, and therefore, the development of new materials is continuously required.

[0008] The present specification describes compounds and organic light-emitting devices comprising the same.

[0009] One embodiment of the present disclosure provides a compound of the following chemical formula 1.

[0010] [Chemical Formula 1]

[0011]

[0012] [Chemical Formula 2]

[0013]

[0014] In the above chemical formula 1,

[0015] X1 to X3 are the same or different from each other, and are each independently N or CR, but at least two of X1 to X3 are N,

[0016] R is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms,

[0017] Ar1 and Ar2 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

[0018] Ar3 is a phenyl group substituted with one or more cyano groups; a biphenyl group substituted with one or more cyano groups; a terphenyl group substituted with one or more cyano groups; or the above chemical formula 2 substituted with one or more cyano groups,

[0019] R1 and R2 are the same or different, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,

[0020] HAr is a triazinyl group substituted with two substituents each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; a pyrimidinyl group substituted with one to three substituents each independently selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; a quinazolinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; A benzothienopyrimidinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a benzofuropyrimidinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

[0021] n is an integer from 1 to 3,

[0022] m is an integer from 1 to 4,

[0023] When n is 2 or more, R1 are equal or different,

[0024] When m is 2 or more, R2 are equal or different,

[0025] In the above chemical formula 2,

[0026] * is the site that binds to chemical formula 1,

[0027] a is 0 or 1,

[0028] b is either 0 or 1.

[0029] In addition, according to one embodiment of the present invention, an organic light-emitting device is provided, including a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers includes the compound described above.

[0030] The compound of the present invention can be used as a material for an organic layer of an organic light-emitting device. When an organic light-emitting device is manufactured by including the compound of the present invention, an organic light-emitting device having high efficiency, low voltage, and long life characteristics can be obtained. In addition, when the compound of the present invention is included in an electron transport layer of an organic light-emitting device, the intramolecular polarization is high, thereby enhancing the effect of electron transfer, and thus an organic light-emitting device having long life characteristics can be manufactured.

[0031] The organic light-emitting device of the present invention is characterized by including a compound represented by Chemical Formula 1. At this time, the compound of the present invention has a LUMO orbital energy of an appropriate energy barrier of -2.8 to -3.2 eV by substituting a linking group between two heterocyclic groups in the para and meta directions, and the planarity of the material is increased to maximize electron mobility, thereby exhibiting high efficiency characteristics, and a cyano group with excellent polarizability is substituted to maintain long-life characteristics.

[0032] Figures 1 to 3 illustrate examples of organic light-emitting devices according to the present invention.

[0033] 1: Substrate

[0034] 2: Anode

[0035] 3: Organic layer

[0036] 4: Cathode

[0037] 5: Hole injection layer

[0038] 6: Hole transport layer

[0039] 6-1: First hole transport layer

[0040] 6-2: Second hole transport layer

[0041] 7: Electron blocking layer

[0042] 8: Emissive layer

[0043] 9: Electron injection and transport layer

[0044] The following describes this specification in more detail.

[0045] In this specification, when a part is said to "include" a certain component, this does not mean that it excludes other components, but rather that it may include other components, unless otherwise specifically stated.

[0046] In this specification, when it is said that a member is located “on” another member, this includes not only cases where the member is in contact with the other member, but also cases where another member exists between the two members.

[0047] In this specification, “dotted line (---)” means a position bonded to a chemical formula or compound.

[0048] In the present specification, the deuterium substitution rate of a compound can be determined by a method of calculating the substitution rate based on the max. value of the distribution of molecular weights at the end of the reaction using TLC-MS (Thin-Layer Chromatography / Mass Spectrometry), or by a quantitative analysis method using NMR, adding DMF as an internal standard, and calculating the D-substitution rate from the total peak integration amount using the integration ratio on 1H NMR.

[0049] 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.

[0050] For example, if the structure is dibenzofuran, the dibenzofuran being “25% deuterated,” the dibenzofuran having a “degree of deuteration of 25%,” or the dibenzofuran having a “deuterium substitution rate of 25%” may mean that two of the eight hydrogens at substitutable positions of the dibenzofuran are substituted or unsubstituted with deuterium.

[0051] In the present specification, the hydrogens that can be substituted with deuterium in the structure may be substituted with deuterium in a range of 0% to 100%, 0.1% to 99.99%, or up to 100%. For example, when the structure is dibenzofuran, the dibenzofuran being "25% deuterated", the "degree of deuteration of 25%" of the dibenzofuran, or the "deuterium substitution rate of 25%" of the dibenzofuran may mean that 2 out of 8 hydrogens at substitutable positions of the dibenzofuran are substituted with deuterium, and the "deuterium substitution rate of 50%" may mean that 4 out of 8 hydrogens at substitutable positions of the dibenzofuran are substituted with deuterium.

[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 position of substitution is not limited as long as it is a position where the hydrogen atom is replaced, i.e., a position where the substituent can be replaced, and when two or more are substituted, the two or more substituents may be the same or different from each other.

[0053] The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group (-CN); a nitro group; a hydroxyl group; an alkyl group; a cycloalkyl group; an alkoxy group; a phosphine oxide group; an aryloxy group; an alkylthioxy group; an arylthioxy group; an alkylsulfoxy group; an arylsulfoxy group; an alkenyl group; a silyl group; a boron group; an amine group; an aryl group; and a heterocyclic group, or substituted with a substituent in which two or more of the above-mentioned substituents are connected, or having no substituents. For example, "a substituent connected with two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent in which two phenyl groups are connected.

[0054] The term "substituted or unsubstituted" in this specification means substituted with one or more substituents selected from the group consisting of deuterium; halogen group; cyano group; silyl group; alkoxy group; aryloxy group; alkyl group; aryl group; and heterocyclic group, or substituted with a substituent in which two or more of the above-mentioned substituents are linked, or having no substituents.

[0055] The term "substituted or unsubstituted" in this specification means substituted with one or more substituents selected from the group consisting of deuterium; alkyl groups; aryl groups; and heterocyclic groups, or substituted with a substituent in which two or more of the above-mentioned substituents are linked, or having no substituents.

[0056] In this specification, the connection of two or more substituents means that the hydrogen of one substituent is connected to another substituent. For example, an isopropyl group and a phenyl group are connected. or can be a substituent of .

[0057] In the present specification, the connection of three substituents includes not only the connection of (substituent 1)-(substituent 2)-(substituent 3) in series, but also the connection of (substituent 2) and (substituent 3) to (substituent 1). For example, two phenyl groups and an isopropyl group are connected. or It can be a substituent of . The same applies to cases where 4 or more substituents are connected.

[0058] Examples of the above substituents are described below, but are not limited thereto.

[0059] In this specification, examples of halogen groups include fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0060] In the present specification, a silyl group may be represented by the chemical formula -SiYaYbYc, wherein Ya, Yb, and Yc may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0061] In the present specification, the boron group may be represented by the chemical formula -BYdYe, wherein Yd and Ye may each be hydrogen; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. The boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a t-butyldimethylboron group, a triphenylboron group, and a phenylboron group.

[0062] In the present specification, the alkyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an n-propyl group, an isopropyl group, a butyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, an n-pentyl group, a hexyl group, an n-hexyl group, a heptyl group, an n-heptyl group, an octyl group, an n-octyl group, etc.

[0063] In the present specification, the propyl group includes an n-propyl group and an isopropyl group.

[0064] In this specification, the description of the alkyl group described above may be applied to the arylalkyl group, except that the arylalkyl group is substituted with an aryl group.

[0065] In the present specification, the alkoxy group may be linear, branched, or cyclic. The carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms. Specifically, it may be methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, etc., but is not limited thereto.

[0066] Substituents comprising alkyl groups, alkoxy groups and other alkyl moieties described herein include both straight-chain and branched forms.

[0067] In the present specification, the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms in the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 6. Specific examples include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-(naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, stilbenyl, and styrenyl.

[0068] In the present specification, the alkynyl group is a substituent containing a triple bond between carbon atoms, may be straight or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms in the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms in the alkenyl group is 2 to 10.

[0069] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. In one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, examples thereof include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0070] In the present specification, the amine group is -NH2, and the amine group may be substituted with the above-mentioned alkyl group, aryl group, heterocyclic group, alkenyl group, cycloalkyl group, and combinations thereof. The carbon number of the substituted amine group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the carbon number of the amine group is 1 to 20. According to one embodiment, the carbon number of the amine group is 1 to 10. Specific examples of substituted amine groups include, but are not limited to, a methylamine group, a dimethylamine group, an ethylamine group, a diethylamine group, a phenylamine group, a 9,9-dimethylfluorenylphenylamine group, a pyridylphenylamine group, a diphenylamine group, a phenylpyridylamine group, a naphthylamine group, a biphenylamine group, anthracenylamine group, a dibenzofuranylphenylamine group, a 9-methylanthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a ditolylamine group, a phenyltolylamine group, a diphenylamine group, and the like.

[0071] In the present specification, the aryl group is not particularly limited, but is preferably one having 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a monocyclic aryl group or a polycyclic aryl group (an aryl group having two or more rings). The monocyclic aryl group may refer to a phenyl group; or a group in which two or more phenyl groups are connected. The monocyclic aryl group may include, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, a quaternaryl group, and the like. The polycyclic aryl group may refer to a group in which two or more monocyclic rings are condensed, such as a naphthyl group or a phenanthrenyl group. The above polycyclic aryl group may include, but is not limited to, a naphthyl group, anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a chrysenyl group, a fluorenyl group, a triphenylenyl group, etc.

[0072] In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.

[0073] When the above fluorenyl group is substituted, , Spirofluorenyl group of etc. (9,9-dimethylfluorenyl group), and It can be a substituted fluorenyl group such as (9,9-diphenylfluorenyl group), but is not limited thereto.

[0074] In this specification, the aryl group among the aryloxy groups may be applied to the description of the aryl group described above.

[0075] In the present specification, a heterocyclic group is a ring group containing at least one of N, O, P, S, Si, and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. 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 the heterocyclic group include, but are not limited to, a pyridine group, a pyrrole group, a pyrimidine group, a quinoline group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a benzocarbazole group, a naphthobenzofuran group, a benzonaphthothiophene group, an indenocarbazole group, a triazinyl group, and the like.

[0076] In this specification, the description of the heterocyclic group described above may be applied, except that the heteroaryl group is aromatic.

[0077] In the present specification, a heteroaryl group includes one or more non-carbon atoms or heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, and S. The number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic. Examples of heteroaryl groups include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, pyridine group, bipyridine group, pyrimidine group, triazine group, triazole group, acridine group, pyridazine group, pyrazine group, quinoline group, quinazoline group, quinoxaline group, phthalazine group, pyridopyrimidine group, pyridopyrazine group, pyrazinopyrazine group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuran group, phenanthridine, phenanthroline, isoxazole group, thiadiazole group, Examples thereof include, but are not limited to, dibenzofuran group, dibenzosilole group, phenoxathiine group, phenoxazine group, phenothiazine group, dihydroindenocarbazole group, spirofluorenxanthene group, and spirofluorenethioxanthene group.

[0078] In this specification, the description of the aryl group may be applied except that the arylene group is divalent.

[0079] In this specification, the description of the above heterocyclic group may be applied to the divalent heterocyclic group except that the divalent heterocyclic group is divalent.

[0080] In this specification, the description of the above aryl group may be applied to the n+1 valent aryl group, except that the aryl group is n+1 valent.

[0081] In this specification, the description of the above heterocyclic group may be applied to the n+1-valent heterocyclic group, except that the heterocyclic group is n+1-valent.

[0082] In the present specification, in a substituted or unsubstituted ring formed by bonding with adjacent groups, “ring” means a hydrocarbon ring; or a heterocycle.

[0083] The above hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the above cycloalkyl group or aryl group.

[0084] In the present specification, forming a ring by bonding with adjacent groups means forming a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; a substituted or unsubstituted aromatic heterocycle; or a condensed ring thereof by bonding with adjacent groups. The hydrocarbon ring means a ring composed only of carbon and hydrogen atoms. The heterocycle means a ring containing one or more selected from N, O, P, S, Si, and Se. In the present specification, the aliphatic hydrocarbon ring, the aromatic hydrocarbon ring, the aliphatic heterocycle, and the aromatic heterocycle may be monocyclic or polycyclic.

[0085] In this specification, an aliphatic hydrocarbon ring means 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.

[0086] In this specification, an aromatic hydrocarbon ring means 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 can be interpreted to have the same meaning as an aryl group.

[0087] In the present specification, an aliphatic heterocycle means an aliphatic ring containing at least one heteroatom. Examples of aliphatic heterocycles include, but are not limited to, oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane, azocane, and thiocane.

[0088] In this specification, an aromatic heterocycle means an aromatic ring containing at least one heteroatom. Examples of aromatic heterocycles include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, parazole, oxazole, isoxazole, thiazole, isothiazole, triazole, oxadiazole, thiadiazole, dithiazole, tetrazole, pyran, thiopyran, diazine, oxazine, thiazine, dioxin, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthyridine, acridine, phenanthridine, diazanaphthalene, dryazaindene, indole, indolizine, benzothiazole, benzoxazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenazine, Examples include, but are not limited to, imidazopyridine, phenoxazine, indolocarbazole, and indenocarbazole.

[0089] In this specification, the term "fused ring" refers to a ring-shaped structure in which two or more rings share two or more atoms. The fused ring may be an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or a fused ring of an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, but is not limited thereto.

[0090] In the present specification, a fused aromatic hydrocarbon ring group means a ring in which two or more aromatic hydrocarbon rings are fused. Examples of the fused aromatic hydrocarbon ring group include, but are not limited to, a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenylene group, chrysenyl group, fluorenyl group, and triphenylenyl group.

[0091] Unless otherwise defined herein, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety, and in case of conflict, this specification, including definitions, will control unless a specific passage is cited. Furthermore, the materials, methods, and examples are illustrative only and not intended to be limiting.

[0092] In this specification, a position that can be substituted with hydrogen in the chemical formula 1 can be substituted with deuterium.

[0093] In the present specification, a position that can be substituted with hydrogen in the chemical formula 2 substituted with one or more cyano groups may be substituted with deuterium.

[0094] In the present specification, Ar3 of the chemical formula 1 may be a phenyl group substituted with one or more cyano groups; a biphenyl group substituted with one or more cyano groups; a terphenyl group substituted with one or more cyano groups; or a chemical formula 2 substituted with one or more cyano groups, and a position that can be substituted with hydrogen in the biphenyl group; the biphenyl group; the terphenyl group or the chemical formula 2 substituted with one or more cyano groups may be substituted with deuterium.

[0095] In the present specification, HAr of the above chemical formula 1 is a triazinyl group substituted with two substituents each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; a pyrimidinyl group substituted with one to three substituents each independently selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; a quinazolinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; A benzothienopyrimidinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a benzofuropyrimidinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; and a position that can be substituted with hydrogen of the triazinyl group; pyrimidinyl group; quinazolinyl group; benzothienopyrimidinyl group; or benzofuropyrimidinyl group can be substituted with deuterium.

[0096] According to one embodiment of the present specification, the HAr is a triazinyl group substituted with two substituents each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; a pyrimidinyl group substituted with one to three substituents each independently selected from the group consisting of a deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; a quinazolinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; A benzothienopyrimidinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a benzofuropyrimidinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0097] According to one embodiment of the present specification, the HAr is a triazinyl group substituted with two substituents each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; a pyrimidinyl group substituted with one to three substituents each independently selected from the group consisting of a deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; a quinazolinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; A benzothienopyrimidinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms; or a benzofuropyrimidinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0098] According to one embodiment of the present specification, the HAr is a triazinyl group substituted with two substituents each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; a pyrimidinyl group substituted with one to three substituents each independently selected from the group consisting of a deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; a quinazolinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; A benzothienopyrimidinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms; or a benzofuropyrimidinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0099] According to one embodiment of the present specification, the HAr is a triazinyl group substituted with two substituents each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms; a pyrimidinyl group substituted with one to three substituents each independently selected from the group consisting of a deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms; a quinazolinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms; A benzothienopyrimidinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms; or a benzofuropyrimidinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.

[0100] According to one embodiment of the present specification, the HAr is a triazinyl group substituted with two substituents each independently selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, and a substituted or unsubstituted pyrimidinyl group; a pyrimidinyl group substituted with one to three substituents each independently selected from the group consisting of deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted methyl group, a substituted or unsubstituted ethyl group, a substituted or unsubstituted propyl group, and a substituted or unsubstituted pyridinyl group; a quinazolinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, and a substituted or unsubstituted naphthyl group; A benzothienopyrimidinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, and a substituted or unsubstituted naphthyl group; or a benzofuropyrimidinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, and a substituted or unsubstituted naphthyl group.

[0101] According to one embodiment of the present specification, the HAr is a triazinyl group substituted with two substituents each independently selected from the group consisting of a phenyl group substituted or unsubstituted with a deuterium or alkyl group, a biphenyl group substituted or unsubstituted with a deuterium or alkyl group, a naphthyl group substituted or unsubstituted with a deuterium or alkyl group, and a pyrimidinyl group substituted or unsubstituted with a deuterium or alkyl group; A pyrimidinyl group substituted with 1 to 3 substituents each independently selected from the group consisting of a phenyl group substituted or unsubstituted with deuterium, deuterium or an alkyl group, a biphenyl group substituted or unsubstituted with deuterium or an alkyl group, a naphthyl group substituted or unsubstituted with deuterium or an alkyl group, a methyl group substituted or unsubstituted with deuterium or an alkyl group, an ethyl group substituted or unsubstituted with deuterium or an alkyl group, a propyl group substituted or unsubstituted with deuterium or an alkyl group, and a pyridinyl group substituted or unsubstituted with deuterium or an alkyl group; A quinazolinyl group substituted with 1 substituent selected from the group consisting of a phenyl group substituted or unsubstituted with deuterium or an alkyl group, a biphenyl group substituted or unsubstituted with deuterium or an alkyl group, and a naphthyl group substituted or unsubstituted with deuterium or an alkyl group; A benzothienopyrimidinyl group substituted with one substituent selected from the group consisting of a phenyl group substituted or unsubstituted with a deuterium or alkyl group, a biphenyl group substituted or unsubstituted with a deuterium or alkyl group, and a naphthyl group substituted or unsubstituted with a deuterium or alkyl group; or a benzofuropyrimidinyl group substituted with one substituent selected from the group consisting of a phenyl group substituted or unsubstituted with a deuterium or alkyl group, a biphenyl group substituted or unsubstituted with a deuterium or alkyl group, and a naphthyl group substituted or unsubstituted with a deuterium or alkyl group.

[0102] In this specification, the chemical formula 1 is any one of the following chemical formulas 1-1 to 1-5.

[0103] [Chemical Formula 1-1]

[0104]

[0105] [Chemical Formula 1-2]

[0106]

[0107] [Chemical Formula 1-3]

[0108]

[0109] [Chemical Formula 1-4]

[0110]

[0111] [Chemical Formula 1-5]

[0112]

[0113] In the above chemical formulas 1-1 to 1-5,

[0114] The above X1 to X3, Ar1 to Ar3, n and m are as defined in the above chemical formula 1,

[0115] R1 and R2 are the same or different and are each independently hydrogen or deuterium,

[0116] R3 and R4 are the same or different, and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

[0117] R5 is deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

[0118] R6 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,

[0119] o is an integer from 1 to 3,

[0120] When o is 2 or more, R5 are equal or different.

[0121] In this specification, the chemical formula 1 is the chemical formula 1-1.

[0122] In this specification, the chemical formula 1 is the chemical formula 1-2.

[0123] In this specification, the chemical formula 1 is the chemical formula 1-3.

[0124] In this specification, the chemical formula 1 is the chemical formula 1-4.

[0125] In this specification, the chemical formula 1 is the chemical formula 1-5.

[0126] According to one embodiment of the present specification, X1 to X3 are the same as or different from each other, and are each independently N or CR, and at least two of X1 to X3 are N.

[0127] In one embodiment of the present specification, two or more of X1 to X3 are N.

[0128] In one embodiment of the present specification, X1 and X2 are N.

[0129] In one embodiment of the present specification, X1 and X3 are N.

[0130] In one embodiment of the present specification, X2 and X3 are N.

[0131] In one embodiment of the present specification, X1 to X3 are all N.

[0132] In one embodiment of the present specification, R is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0133] In one embodiment of the present specification, R is hydrogen; or deuterium.

[0134] According to one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0135] According to one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0136] According to one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0137] According to one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted pyrimidinyl group; or a substituted or unsubstituted quinazolinyl group.

[0138] According to one embodiment of the present specification, Ar1 and Ar2 are the same as or different from each other, and each independently represent a phenyl group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms; a pyrimidinyl group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms; or a quinazolinyl group unsubstituted or substituted with deuterium, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

[0139] According to one embodiment of the present specification, Ar3 is a phenyl group substituted with one cyano group; a biphenyl group substituted with one cyano group; a terphenyl group substituted with one cyano group; or a group of chemical formula 2 substituted with one cyano group.

[0140] According to one embodiment of the present specification, Ar3 is a phenyl group substituted with two cyano groups; a biphenyl group substituted with two cyano groups; a terphenyl group substituted with two cyano groups; or a group of chemical formula 2 substituted with two cyano groups.

[0141] According to one embodiment of the present specification, Ar3 is a phenyl group substituted with one or two cyano groups; a biphenyl group substituted with one or two cyano groups; a terphenyl group substituted with one or two cyano groups; or a group of chemical formula 2 substituted with one or two cyano groups.

[0142] According to one embodiment of the present specification, Ar3 is a phenyl group substituted with three cyano groups; a biphenyl group substituted with three cyano groups; or a terphenyl group substituted with three cyano groups.

[0143] According to one embodiment of the present specification, the Ar3 is the chemical formula 2 substituted with one or more cyano groups.

[0144] According to one embodiment of the present specification, the Ar3 is the chemical formula 2 substituted with one cyano group.

[0145] According to one embodiment of the present specification, the Ar3 is the chemical formula 2 substituted with two cyano groups.

[0146] According to one embodiment of the present specification, the Ar3 is the chemical formula 2 substituted with one or two cyano groups.

[0147] According to one embodiment of the present specification, the Ar3 is the chemical formula 2 substituted with three cyano groups.

[0148] According to one embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0149] According to one embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0150] According to one embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0151] According to one embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.

[0152] According to one embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted pyridinyl group.

[0153] According to one embodiment of the present specification, R3 and R4 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with deuterium, a methyl group, or a pyrimidinyl group; a biphenyl group unsubstituted or substituted with deuterium, a methyl group, or a pyrimidinyl group; a naphthyl group unsubstituted or substituted with deuterium, a methyl group, or a pyrimidinyl group; or a pyridinyl group unsubstituted or substituted with deuterium, a methyl group, or a pyrimidinyl group.

[0154] According to one embodiment of the present specification, R5 is deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0155] According to one embodiment of the present specification, R5 is deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0156] According to one embodiment of the present specification, R5 is deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0157] According to one embodiment of the present specification, R5 is deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.

[0158] According to one embodiment of the present specification, R5 is deuterium; a methyl group; an ethyl group; a propyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted pyridinyl group.

[0159] According to one embodiment of the present specification, R5 is deuterium; a methyl group; an ethyl group; a propyl group; a phenyl group unsubstituted or substituted with deuterium or an alkyl group; a biphenyl group unsubstituted or substituted with deuterium or an alkyl group; a naphthyl group unsubstituted or substituted with deuterium or an alkyl group; or a pyridinyl group unsubstituted or substituted with deuterium or an alkyl group.

[0160] According to one embodiment of the present specification, R6 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.

[0161] According to one embodiment of the present specification, R6 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0162] According to one embodiment of the present specification, R6 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0163] According to one embodiment of the present specification, R6 is a substituted or unsubstituted aryl group having 6 to 10 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.

[0164] According to one embodiment of the present specification, R6 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted pyridinyl group.

[0165] According to one embodiment of the present specification, R6 is a phenyl group unsubstituted or substituted with a deuterium or alkyl group; a biphenyl group unsubstituted or substituted with a deuterium or alkyl group; a naphthyl group unsubstituted or substituted with a deuterium or alkyl group; or a pyridinyl group unsubstituted or substituted with a deuterium or alkyl group.

[0166] According to one embodiment of the present specification, n is an integer from 1 to 3.

[0167] According to one embodiment of the present specification, n is 1.

[0168] According to one embodiment of the present specification, n is 2.

[0169] According to one embodiment of the present specification, n is 3.

[0170] According to one embodiment of the present specification, m is an integer from 1 to 4.

[0171] According to one embodiment of the present specification, m is 1.

[0172] According to one embodiment of the present specification, m is 2.

[0173] According to one embodiment of the present specification, m is 3.

[0174] According to one embodiment of the present specification, m is 4.

[0175] According to one embodiment of the present specification, o is an integer from 1 to 3.

[0176] According to one embodiment of the present specification, o is 1.

[0177] According to one embodiment of the present specification, o is 2.

[0178] According to one embodiment of the present specification, the o is 3.

[0179] According to one embodiment of the present specification, a is 0 or 1.

[0180] According to one embodiment of the present specification, a is 0.

[0181] According to one embodiment of the present specification, a is 1.

[0182] According to one embodiment of the present specification, b is 0 or 1.

[0183] According to one embodiment of the present specification, b is 0.

[0184] According to one embodiment of the present specification, b is 1.

[0185] According to one embodiment of the present specification, the chemical formula 1-3 is the following chemical formula 1-3-1 or chemical formula 1-3-2.

[0186] [Chemical Formula 1-3-1]

[0187]

[0188] [Chemical Formula 1-3-2]

[0189]

[0190] In the above chemical formulas 1-3-1 and 1-3-2,

[0191] X1 to X3, Ar1 to Ar3, n, m, R1, R2 and R6 are as defined in the above chemical formula 1-3.

[0192] According to one embodiment of the present specification, the Ar3 is represented by one of the following structural formulas.

[0193]

[0194]

[0195]

[0196]

[0197] In the above structural formula, the dotted line indicates a bonding position, and the above structural formula can be substituted with one or more deuterium atoms.

[0198] According to one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0199] According to one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0200] According to one embodiment of the present specification, R1 and R2 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0201] According to one embodiment of the present specification, R1 and R2 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0202] According to one embodiment of the present specification, both R1 and R2 are hydrogen.

[0203] According to one embodiment of the present specification, both R1 and R2 are deuterium.

[0204] In this specification, the chemical formula 1 is any one of the structural formulas below.

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214] .

[0215] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 30% or more.

[0216] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 40% or more.

[0217] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 50% or more.

[0218] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 60% or more.

[0219] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 70% or more.

[0220] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 80% or more.

[0221] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 90% or more.

[0222] According to one embodiment of the present specification, the deuterium substitution rate of the chemical formula 1 is 100%.

[0223] The substituent of the compound of the above chemical formula 1 can be combined by a method known in the art, and the type, position or number of the substituent can be changed according to a technique known in the art.

[0224] In addition, by introducing various substituents into the core structure as described above, compounds having the unique properties of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport materials, light-emitting layer materials, and electron transport layer materials used in the manufacture of organic light-emitting devices into the core structure, a material satisfying the conditions required for each organic layer can be synthesized.

[0225] In addition, the organic light-emitting device according to the present invention is an organic light-emitting device comprising a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises the compound described above.

[0226] The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.

[0227] The above compound can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0228] The organic layer of the organic light-emitting device of the present invention may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a layer that simultaneously injects holes and transports holes, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers or a larger number of organic layers.

[0229] In the organic light-emitting device of the present invention, the organic layer may include at least one of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and at least one of the layers may include a compound represented by the chemical formula 1.

[0230] In the organic light-emitting device of the present invention, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include a compound represented by the chemical formula 1.

[0231] In the organic light-emitting device of the present invention, the electron injection and transport layer includes the compound of the chemical formula 1 and a metal complex.

[0232] In the organic light-emitting device of the present invention, the organic layer may include at least one layer among a hole injection layer, a hole transport layer, and a layer that simultaneously injects holes and transports holes, and at least one layer among the layers may include a compound represented by the chemical formula 1.

[0233] In another organic light-emitting device, the organic layer may include a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer may include a compound represented by the chemical formula 1.

[0234] In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

[0235] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0236] (1) Anode / hole transport layer / light emitting layer / cathode

[0237] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0238] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0239] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0240] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0241] (6) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0242] (7) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0243] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0244] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0245] (10) Anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

[0246] (11) Anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0247] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

[0248] (13) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0249] (14) Anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

[0250] (15) Anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0251] (16) Anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

[0252] (17) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0253] (18) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron injection and transport layer / cathode

[0254] (19) Anode / hole injection layer / hole transport layer / light-emitting layer / electron injection and transport layer / cathode

[0255] (20) Anode / hole injection layer / first hole transport layer / second hole transport layer / light-emitting layer / electron injection and transport layer / cathode

[0256] The structure of the organic light-emitting device of the present invention may have a structure as shown in FIGS. 1 to 3, but is not limited thereto.

[0257] Figure 1 illustrates the structure of an organic light-emitting device in which an anode (2), an organic layer (3), and a cathode (4) are sequentially laminated on a substrate (1). In this structure, the compound represented by the chemical formula 1 may be included in the organic layer (3).

[0258] FIG. 2 illustrates the structure of an organic light-emitting device in which an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light-emitting layer (8), an electron injection and transport layer (9), and a cathode (4) are sequentially laminated on a substrate (1). The compound represented by the chemical formula 1 may be included in the electron injection and transport layer (9).

[0259] Figure 3 illustrates the structure of an organic light-emitting device in which an anode (2), a hole injection layer (5), a first hole transport layer (6-1), a second hole transport layer (6-2), a light-emitting layer (8), an electron injection and transport layer (9), and a cathode (4) are sequentially laminated on a substrate (1). The compound represented by the chemical formula 1 may be included in the electron injection and transport layer (9). For example, the organic light-emitting device according to the present invention 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 PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and then forming an organic layer including at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a layer that simultaneously transports and injects holes, a light-emitting layer, an electron transport layer, an electron injection layer, and a layer that simultaneously transports and injects electrons, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0260] The above organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the above organic layer may be manufactured with a smaller number of layers using various polymer materials by a solvent process other than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

[0261] The anode is an electrode that injects holes, and as the anode material, a material having a high work function is generally preferred so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline.

[0262] The above cathode is an electrode that injects electrons, and the cathode material is preferably a material with a low work function to facilitate electron injection into the organic layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF / Al or LiO2 / Al.

[0263] The above hole injection layer is a layer that facilitates the injection of holes from the anode to the light-emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrine, oligothiophene, arylamine series organic materials, hexanitrilehexaazatriphenylene series organic materials, quinacridone series organic materials, perylene series organic materials, anthraquinone, and polyaniline and polythiophene series conductive polymers. The thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage of being able to prevent the hole injection characteristics from being deteriorated, and if it is 150 nm or less, there is an advantage of being able to prevent the driving voltage from being increased to improve the movement of holes due to the thickness of the hole injection layer being too thick.

[0264] According to one embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound represented by the following chemical formula HI-1.

[0265] According to one embodiment of the present specification, the hole injection layer may be a compound of the following chemical formula HI-1.

[0266] [Chemical formula HI-1]

[0267]

[0268] In the above chemical formula HI-1,

[0269] R201 to R205 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to form a substituted or unsubstituted ring,

[0270] R206 is hydrogen; deuterium; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, and r206 is an integer from 0 to 8, and when r206 is 2 or more, R206 are the same as or different from each other.

[0271] In one embodiment of the present specification, R201 is a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or is bonded to an adjacent group to form a substituted or unsubstituted ring.

[0272] In one embodiment of the present specification, R201 is a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0273] In one embodiment of the present specification, R201 is a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0274] In one embodiment of the present specification, R201 is a substituted or unsubstituted aryl group.

[0275] In one embodiment of the present specification, R201 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0276] In one embodiment of the present specification, R201 is a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0277] In one embodiment of the present specification, R201 is a substituted or unsubstituted phenyl group.

[0278] In one embodiment of the present specification, R202 to R205 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0279] In one embodiment of the present specification, R202 to R205 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0280] In one embodiment of the present specification, R202 to R205 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0281] In one embodiment of the present specification, R202 and R204 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group.

[0282] In one embodiment of the present specification, R202 and R204 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0283] In one embodiment of the present specification, R202 and R204 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0284] In one embodiment of the present specification, R202 and R204 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group.

[0285] In one embodiment of the present specification, R203 and R205 are the same as or different from each other, and each independently represents a substituted or unsubstituted heteroaryl group.

[0286] In one embodiment of the present specification, R203 and R205 are the same as or different from each other, and each independently represent a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0287] In one embodiment of the present specification, R203 and R205 are the same as or different from each other, and each independently represent a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.

[0288] In one embodiment of the present specification, R203 and R205 are the same as or different from each other, and each independently represents a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0289] In one embodiment of the present specification, R203 and R205 are the same as or different from each other, and each independently represents a carbazolyl group substituted or unsubstituted with an aryl group.

[0290] In one embodiment of the present specification, R203 and R205 are the same as or different from each other, and each independently represents a carbazolyl group unsubstituted or substituted with a phenyl group.

[0291] In one embodiment of the present specification, R206 is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0292] In one embodiment of the present specification, R206 is hydrogen or deuterium.

[0293] In one embodiment of the present specification, the chemical formula HI-1 may include the following compound.

[0294]

[0295] The above-mentioned hole transport layer can play a role in facilitating hole transport. A suitable hole transport material is one that can transport holes from the anode or hole injection layer and transfer them to the light-emitting layer, and that has high hole mobility. Specific examples include, but are not limited to, arylamine-based organic compounds, conductive polymers, and block copolymers with both conjugated and non-conjugated portions.

[0296] According to one embodiment of the present specification, the hole transport layer includes, but is not limited to, a compound of the following chemical formula HT-1.

[0297] [Chemical formula HT-1]

[0298]

[0299] In the above chemical formula HT-1,

[0300] At least one of X'1 to X'6 is N, and the rest are CH,

[0301] R309 to R314 are the same or different, and each independently represent hydrogen; deuterium; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to form a substituted or unsubstituted ring.

[0302] According to one embodiment of the present specification, X'1 to X'6 are N.

[0303] According to one embodiment of the present specification, R309 to R314 are cyano groups.

[0304] According to one embodiment of the present specification, the chemical formula HT-1 may include the following compound.

[0305]

[0306] According to one embodiment of the present specification, the hole transport layer includes, but is not limited to, a compound represented by the following chemical formula HT-2.

[0307] [Chemical formula HT-2]

[0308]

[0309] In the above chemical formula HT-2,

[0310] R315 to R317 are the same or different, and each independently represent one 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 combine with adjacent groups to form a substituted or unsubstituted ring,

[0311] r315 is an integer from 1 to 5, and when r315 is 2 or more, 2 or more R315 are the same as or different from each other,

[0312] r316 is an integer from 1 to 5, and when r316 is 2 or more, two or more R316 are the same as or different from each other.

[0313] 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 a combination thereof.

[0314] According to one embodiment of the present specification, R317 is a substituted or unsubstituted phenyl group; or a substituted or unsubstituted fluorene group, or adjacent groups are bonded to each other to form a substituted or unsubstituted ring group.

[0315] According to one embodiment of the present specification, R317 is a substituted or unsubstituted phenyl group; or a fluorene group substituted or unsubstituted with an alkyl group, or the phenyl group or fluorene group can form a condensed ring.

[0316] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted carbazole group.

[0317] According to one embodiment of the present specification, the chemical formula HT-2 is represented by the following compound.

[0318]

[0319] According to one embodiment of the present specification, the hole transport layer may include a compound of the chemical formula HT-1 and / or a compound of the chemical formula HT-2.

[0320] According to one embodiment of the present specification, the hole transport layer may be composed of a first hole transport layer and a second hole transport layer.

[0321] According to one embodiment of the present specification, the first hole transport layer may include a compound of the chemical formula HT-1.

[0322] According to one embodiment of the present specification, the second hole transport layer may include a compound of the chemical formula HT-2.

[0323] The above-mentioned light-emitting layer can emit red, green, or blue light, and can be made of a phosphorescent material or a fluorescent material. The above-mentioned light-emitting material is a material that can emit light in the visible light range by transporting holes and electrons from a hole transport layer and an electron transport layer, respectively, and combining them, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole series compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; benzoxazole, benzthiazole, and benzimidazole series compounds; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc.

[0324] Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocyclic compound-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compound-containing compounds include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc.

[0325] According to one embodiment of the present disclosure, the host includes, but is not limited to, a compound of the following chemical formula H-1.

[0326] [Chemical Formula H-1]

[0327]

[0328] In the above chemical formula H-1,

[0329] L20 and L21 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

[0330] Ar20 and Ar21 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0331] R201 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0332] r201 is an integer from 1 to 8, and when r201 is 2 or more, 2 or more R201 are the same as or different from each other.

[0333] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently represents a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.

[0334] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently represent a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylylene group substituted or unsubstituted with deuterium; a naphthylene group substituted or unsubstituted with deuterium; a divalent dibenzofuran group; or a divalent dibenzothiophene group.

[0335] In one embodiment of the present specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

[0336] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0337] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

[0338] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represent a phenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a thiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or, it is a naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0339] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group; a naphthyl group substituted or unsubstituted with deuterium; a thiophene group substituted or unsubstituted with a phenyl group; a phenanthrene group; a dibenzofuran group; a naphthobenzofuran group; a dibenzothiophene group; or a naphthobenzothiophene group.

[0340] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a phenyl group, a 1-naphthyl group, or a 2-naphthyl group.

[0341] According to one embodiment of the present specification, R201 is hydrogen or a naphthyl group.

[0342] According to one embodiment of the present specification, the chemical formula H-1 may include the following compound.

[0343]

[0344] When the light-emitting layer emits red light, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum), or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) can 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) can be used as light-emitting dopants, but are not limited thereto. When the light-emitting layer emits blue light, a phosphorescent material such as (4,6-F2ppy)2Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distriarylene (DSA), PFO polymer, or PPV polymer can be used as a light-emitting dopant, but is not limited thereto.

[0345] In one embodiment of the present specification, the dopant includes a compound of the following chemical formula D-1.

[0346] [Chemical Formula D-1]

[0347]

[0348] In the above chemical formula D-1,

[0349] L401 and L402 are the same or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted arylene group,

[0350] R401 to R404 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0351] In one embodiment of the present specification, L401 and L402 are each direct bonds.

[0352] In one embodiment of the present specification, R401 to R404 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0353] In one embodiment of the present specification, R401 to R404 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic aryl group; a substituted or unsubstituted polycyclic aryl group; or a substituted or unsubstituted heterocyclic group.

[0354] In one embodiment of the present specification, R401 to R404 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted pyrene group; or a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0355] In one embodiment of the present specification, R401 to R404 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; or a substituted or unsubstituted dibenzofuran group.

[0356] In one embodiment of the present specification, R401 to R404 are the same as or different from each other, and each independently represents a phenyl group substituted or unsubstituted with one or more substituents selected from the group consisting of an alkyl group, a silyl group, and an aryl group.

[0357] In one embodiment of the present specification, R401 to R404 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with one or more substituents selected from the group consisting of a methyl group; a tert-butyl group; a trimethylsilyl group; and a phenyl group substituted with an alkyl group.

[0358] In one embodiment of the present specification, the chemical formula D-1 is represented by the following compound.

[0359]

[0360] The above electron transport layer can play a role in facilitating electron transport. As the electron transport material, a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is suitable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The thickness of the electron transport layer may be 1 to 50 nm. When the thickness of the electron transport layer is 1 nm or more, there is an advantage in that the electron transport characteristics can be prevented from being deteriorated, and when the thickness of the electron transport layer is 50 nm or less, there is an advantage in that the driving voltage can be prevented from increasing to improve electron movement due to the electron transport layer being too thick.

[0361] The above electron injection layer can play a role in facilitating electron injection. As the electron injection material, a compound having the ability to transport electrons, an excellent electron injection effect from the cathode, an excellent electron injection effect for the light-emitting layer or light-emitting material, a compound that prevents the movement of excitons generated in the light-emitting layer to the hole injection layer, and an excellent thin film forming ability is preferable. Specifically, examples thereof include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0362] The above electron injection and transport layer can be manufactured by appropriately selecting the material used in the electron injection layer and electron transport layer.

[0363] The above electron injection and transport layer can be manufactured using the compound of the above chemical formula 1.

[0364] The above electron injection and transport layer can be manufactured by using the compound of the above chemical formula 1 and a metal complex together.

[0365] The above electron injection and transport layer contains the compound of the above chemical formula 1 and the metal complex in a weight ratio of 1:10 to 10:1.

[0366] The above electron injection and transport layer contains the compound of the above chemical formula 1 and the metal complex in a weight ratio of 1:3 to 3:1.

[0367] 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-naphtholato)aluminum, Bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc., but are not limited thereto.

[0368] The above hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed under the same conditions as the hole injection layer. Specifically, examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0369] The organic light-emitting device according to the present invention may be a front-emitting, back-emitting, or double-sided emitting type depending on the material used.

[0370] The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.

[0371] The method for preparing the compound of the above chemical formula 1 and the preparation of an organic light-emitting device using the compound are specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited by them.

[0372] In the following reaction scheme, the type and number of substituents can be appropriately selected by those skilled in the art from known starting materials, enabling the synthesis of various types of intermediates. The reaction types and reaction conditions known in the art can be utilized.

[0373]

[0374] [Manufacturing example]

[0375] Manufacturing Example 1: Preparation of Compound E1

[0376]

[0377] In a nitrogen atmosphere, E1-A (20 g, 45 mmol) and E1-B (19.6 g, 45 mmol) were added to 400 mL of 1,4-dioxane, stirred, and refluxed. Then, potassium triphosphate (28.6 g, 134.9 mmol) dissolved in 29 mL of water was added, and after sufficient stirring, dibenzylideneacetonepalladium (0.8 g, 1.3 mmol) and tricyclohexylphosphine (0.8 g, 2.7 mmol) were added. After 6 hours of reaction, the mixture was cooled to room temperature and the resulting solid was filtered. The solid was added to 968 mL of chloroform, dissolved, washed twice with water, the organic layer was separated, anhydrous magnesium sulfate was added, stirred, filtered, and the filtrate was distilled under reduced pressure. The concentrated compound was recrystallized from chloroform and ethyl acetate to produce a yellow solid compound E1 (4.8 g, 15%).

[0378] MS: [M+H] + = 718

[0379] Manufacturing Example 2: Preparation of Compound E2

[0380]

[0381] Compound E2 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0382] MS: [M+H] + = 845

[0383] Manufacturing Example 3: Preparation of Compound E3

[0384]

[0385] Compound E3 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0386] MS: [M+H] + = 794

[0387] Manufacturing Example 4: Preparation of Compound E4

[0388]

[0389] Compound E4 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0390] MS: [M+H] + = 898

[0391] Manufacturing Example 5: Preparation of Compound E5

[0392]

[0393] Compound E5 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0394] MS: [M+H] + = 870

[0395] Manufacturing Example 6: Preparation of Compound E6

[0396]

[0397] Compound E6 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0398] MS: [M+H] + = 870

[0399] Manufacturing Example 7: Preparation of Compound E7

[0400]

[0401] Compound E7 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction scheme.

[0402] MS: [M+H] + = 691

[0403] Manufacturing Example 8: Preparation of Compound E8

[0404]

[0405] Compound E8 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0406] MS: [M+H] + = 793

[0407] Manufacturing Example 9: Preparation of Compound E9

[0408]

[0409] Compound E9 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0410] MS: [M+H] + = 743

[0411] Manufacturing Example 10: Manufacturing of compound E10

[0412]

[0413] Compound E10 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0414] MS: [M+H] + = 799

[0415] Manufacturing Example 11: Preparation of Compound E11

[0416]

[0417] Compound E11 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0418] MS: [M+H] + = 768

[0419] Manufacturing Example 12: Manufacturing of Compound E12

[0420]

[0421] Compound E12 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0422] MS: [M+H] + = 844

[0423] Manufacturing Example 13: Manufacturing of Compound E13

[0424]

[0425] Compound E13 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0426] MS: [M+H] + = 895

[0427] Manufacturing Example 14: Preparation of Compound E14

[0428]

[0429] Compound E14 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0430] MS: [M+H] + = 844

[0431] Manufacturing Example 15: Preparation of Compound E15

[0432]

[0433] Compound E15 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0434] MS: [M+H] + = 872

[0435] Manufacturing Example 16: Preparation of Compound E16

[0436]

[0437] Compound E16 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0438] MS: [M+H] + = 844

[0439] Manufacturing Example 17: Preparation of Compound E17

[0440]

[0441] Compound E17 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0442] MS: [M+H] + = 843

[0443] Manufacturing Example 18: Manufacturing of Compound E18

[0444]

[0445] Compound E18 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0446] MS: [M+H] + = 791

[0447] Manufacturing Example 19: Preparation of Compound E19

[0448]

[0449] Compound E19 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0450] MS: [M+H] + = 869

[0451] Manufacturing Example 20: Manufacturing of compound E20

[0452]

[0453] Compound E20 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0454] MS: [M+H] + = 793

[0455] Manufacturing Example 21: Manufacturing of Compound E21

[0456]

[0457] Compound E21 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction scheme.

[0458] MS: [M+H] + = 852

[0459] Manufacturing Example 22: Manufacturing of Compound E22

[0460]

[0461] Compound E22 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0462] MS: [M+H] + = 934

[0463]

[0464] [Example]

[0465] Example 1

[0466] A glass substrate coated with a 1,000 Å thick ITO (indium tin oxide) film was placed in distilled water containing detergent and ultrasonically cleaned. The detergent used was a Fischer Co. product, and the distilled water used was distilled water that had been filtered twice through a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonically cleaned twice with distilled water for 10 minutes each. After washing with distilled water, ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum deposition machine.

[0467] On the ITO transparent electrode thus prepared, the following compound HI-A was thermally vacuum deposited to a thickness of 600 Å to form a hole injection layer. On the hole injection layer, the following compound HAT's hexanitrile hexaazatriphenylene (hexaazatriphenylene, 50 Å) and the following compound HT-A (600 Å) were sequentially vacuum deposited to form a hole transport layer. Subsequently, the following compounds BH and BD were vacuum deposited at a weight ratio of 25:1 to a film thickness of 200 Å on the hole transport layer to form a light emitting layer.

[0468] On the above-mentioned light-emitting layer, the compound E1 prepared in the above-mentioned Preparation Example 1 and the following compound [LiQ] (Lithium quinolate) were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 360 Å. On the above-mentioned electron injection and transport layer, lithium fluoride (LiF) was sequentially deposited with a thickness of 10 Å and aluminum was sequentially deposited with a thickness of 1,000 Å to form a cathode.

[0469]

[0470] In the above process, the deposition rate of organic materials was maintained at 0.4 to 0.9 Å / sec, lithium fluoride of the cathode was maintained at 0.3 Å / sec, and aluminum was maintained at 2 Å / sec, and the vacuum during deposition was 1 x 10 -7 5 x 10 -5 Torr was maintained, and an organic light-emitting device was fabricated.

[0471]

[0472] Examples 2 to 22

[0473] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compound described in Table 1 was used instead of compound E1 of Example 1.

[0474]

[0475] Comparative Examples 1 to 11

[0476] An organic light-emitting device was manufactured in the same manner as in Example 1, except that the compounds described in Table 1 below were used instead of Compound E1 of Example 1. In Table 1 below, the compounds ET-1 to ET-11 are as follows.

[0477]

[0478]

[0479] Experimental example

[0480] For the organic light-emitting devices manufactured in Examples 1 to 22 and Comparative Examples 1 to 11, 10 mA / cm 2 The driving voltage, luminous efficiency and color coordinates were measured at a current density of 20 mA / cm 2 The time (T90) required for the initial luminance to reach 90% of the current density was measured. The results are shown in Table 1 below.

[0481] Compound (electron injection and transport layer) voltage (V) (@10 mA / cm) 2 )Efficiency (cd / A) (@10mA / cm) 2 )Color coordinates (x,y)T90(hr)(@20mA / cm2)Experimental Example 1 E14.104.43(0.138, 0.111)223Experimental Example 2 E24.224.30(0.138, 0.111)205Experimental Example 3 E34.024.52(0.138, 0.111)221Experimental Example 4 E44.264.38(0.138, 0.110)245Experimental Example 5 E54.274.35(0.138, 0.111)207Experimental Example 6 E64.314.40(0.138, 0.111)205Experimental Example 7 E74.264.25(0.138, 0.111)201Experimental Example 8 E84.354.17(0.138, 0.110)185 Experimental example 9E94.264.29(0.138, 0.111)268 Experimental example 10E104.024.52(0.138, 0.110)281 Experimental example 11E114.124.41(0.138, 0.111)227 Experimental example 12E124.104.42(0.138, 0.111)223 Experimental example 13E134.184.28(0.138, 0.110)246 Experimental example 14E144.164.40(0.138, 0.111)232 Experimental example 15E154.154.33(0.138, 0.110)230 Experimental example 16E164.104.42(0.138, 0.111)221Experimental example 17E174.204.23(0.138, 0.111)214Experimental example 18E184.194.30(0.138, 0.110)218Experimental example 19E194.244.21(0.138, 0.111)240Experimental example 20E204.314.28(0.138, 0.110)273Experimental example 21E214.164.40(0.138, 0.111)244Experimental example 22E224.284.12(0.138, 0.111)264Comparative experiment example 1ET-14.353.75(0.138, 0.111)37Comparative Experimental Example 2ET-24.393.67(0.138, 0.111)35Comparative Experimental Example 3ET-34.443.88(0.138, 0.111)148Comparative Experimental Example 4ET-44.393.92(0.138, 0.112)157Comparative Experimental Example 5ET-54.443.88(0.138, 0.113)144Comparative Experimental Example 6ET-64.483.79(0.138, 0.114)129Comparative Experimental Example 7ET-74.483.75(0.138, 0.114)126Comparative Experimental Example 8ET-84.393.68(0.138, 0.112)38Comparative Experimental Example 9ET-94.413.66(0.138, 0.113)39Comparative Experimental Example 10ET-104.433.65(0.138, 0.112)40Comparative Experimental Example 11ET-114.473.62(0.138, 0.113)42.

[0482] As described in Table 1 above, it was confirmed that the organic light-emitting device using the compound represented by Chemical Formula 1 of the present invention exhibited excellent characteristics in voltage, efficiency, and lifespan (T90).

[0483] Specifically, the experimental examples including the present compound showed superior effects in voltage, efficiency, or life characteristics compared to Comparative Examples 1, 2, and 8 to 11 including compounds not including a cyano group, Comparative Examples 3 and 4 including comparative examples compounds in which triazine is bonded to the meta position of biphenyl, and Comparative Examples 5 to 7 including comparative examples compounds in which a compound corresponding to HAr is bonded to the ortho position of biphenyl.

[0484] Comparative Examples 1-1 to 1-11 using compounds ET1-1 to ET-11 showed higher driving voltage, lower efficiency, and / or lower lifespan characteristics compared to Examples 1-1 to 1-22 using the compound of the chemical formula 1 of the present invention due to an imbalance in electron transfer in the organic light-emitting device.

Claims

1. A compound of the following chemical formula 1: [Chemical Formula 1] [Chemical Formula 2] In the above chemical formula 1, X1 to X3 are the same or different from each other, and are each independently N or CR, but at least two of X1 to X3 are N, R is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, Ar1 and Ar2 are the same or different from each other, and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, Ar3 is a phenyl group substituted with one or more cyano groups; a biphenyl group substituted with one or more cyano groups; a terphenyl group substituted with one or more cyano groups; or the above chemical formula 2 substituted with one or more cyano groups, R1 and R2 are the same or different, and each independently represent hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, HAr is a triazinyl group substituted with two substituents each independently selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; a pyrimidinyl group substituted with one to three substituents each independently selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; a quinazolinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; A benzothienopyrimidinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms; or a benzofuropyrimidinyl group substituted with one substituent selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, n is an integer from 1 to 3, m is an integer from 1 to 4, When n is 2 or more, R1 are equal or different, When m is 2 or more, R2 are equal or different, In the above chemical formula 2, * is the site that binds to chemical formula 1, a is 0 or 1, b is either 0 or 1.

2. In claim 1, the chemical formula 1 is a compound which is any one of the chemical formulas 1-1 to 1-5 below: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] In the above chemical formulas 1-1 to 1-5, X1 to X3, Ar1 to Ar3, n and m are as defined in the above chemical formula 1, R1 and R2 are the same or different and are each independently hydrogen or deuterium, R3 and R4 are the same or different, and each independently represents a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, R5 is deuterium; a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, R6 is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms, o is an integer from 1 to 3, and when o is 2 or greater, R5 are equal to or different from each other.

3. In claim 1, A compound wherein Ar1 and Ar2 are the same or different and each independently represent a substituted or unsubstituted phenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted pyrimidinyl group; or a substituted or unsubstituted quinazolinyl group.

4. In claim 1, A compound wherein all of the above X1 to X3 are N.

5. In claim 2, A compound wherein R3 and R4 are the same or different and each independently represent a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted pyridinyl group.

6. In claim 2, A compound wherein R5 is deuterium; a methyl group; an ethyl group; a propyl group; a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted pyridinyl group.

7. In claim 2, A compound wherein the above R6 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted pyridinyl group.

8. In claim 1, the compound having the chemical formula 1 is any one of the following structural formulas: .

9. An organic light-emitting device comprising a first electrode; a second electrode; and at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound according to any one of claims 1 to 8.

10. An organic light-emitting device according to claim 9, wherein the organic layer comprises at least one of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and at least one of the layers comprises the compound.

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