Compound and organic light-emitting device comprising same

Abstract

The present specification relates to a compound of Chemical Formula 1 and an organic light-emitting device comprising the same. The compound described in the specification can be used as a material for an organic layer of an organic light-emitting device. The compound according to at least one embodiment of the present specification can achieve an improvement in efficiency, a lower driving voltage, and / or an improvement in lifespan characteristics in an organic light-emitting device. In particular, the compound described in the specification can be used as a material for a light-emitting layer. In addition, the organic light-emitting device has the effects of low driving voltage, high efficiency, and / or long lifetime compared to existing organic light-emitting devices.

Description

TECHNICAL FIELD

[0001] This application claims priority to Korean Patent Application No. 10-2024-0130697, filed on September 26, 2024, and Korean Patent Application No. 10-2025-0118211, filed on August 25, 2025, in the Korean Intellectual Property Office, the contents of all of which are incorporated herein in their entirety.

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

[0003] In the present 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. The organic light emitting device can be roughly classified into two types according to the working principle. The first type is a light emitting device in which a photon flowing into the device from an external light source forms an exciton in an organic layer, the exciton is separated into an electron and a hole, and the electron and the hole are transferred to different electrodes to be used as a current source (voltage source). The second type is a light emitting device in which a voltage or a current is applied to two or more electrodes, and holes and / or electrons are injected into an organic semiconductor material layer forming an interface with the electrodes, and the device operates by the injected electrons and holes.

[0004] Generally, an organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic material. An organic light emitting device using the organic light emitting phenomenon generally has a structure including an anode and a cathode and an organic layer therebetween. Here, in order to improve the efficiency and stability of the organic light emitting device, the organic layer is mostly formed of a multi-layer structure using different materials, respectively, for example, can be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, an electron injection layer, etc. For such a structure of the organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the anode into the organic layer, and electrons are injected from the cathode into the organic layer, and when the injected holes and electrons meet, an exciton is formed, and when the exciton re-travels to a ground state, light is emitted. Such an organic light emitting device is known to have characteristics of self-light emission, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, etc.

[0005] Materials used as the organic layer in the organic light emitting device can be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron blocking material, an electron transport material, an electron injection material, etc., according to the function. According to the light emitting color, the light emitting material has blue, green, red light emitting materials, and yellow and orange light emitting materials required for realizing better natural colors.

[0006] In addition, in order to increase color purity and increase the light emission efficiency based on energy transfer, a host / dopant system can be used as the light emitting material. The principle is that when a dopant having a small energy band gap and excellent light emission efficiency compared to the host that mainly constitutes the light emitting layer is mixed in a small amount in the light emitting layer, the excitons generated in the host are transferred to the dopant to emit light with high efficiency. At this time, the wavelength of the host is shifted to the wavelength range of the dopant, and thus light of a desired wavelength can be obtained depending on the type of dopant used.

[0007] In order to sufficiently exhibit the excellent characteristics of the organic light emitting device described above, the substances that constitute the organic layer in the device, such as a hole injecting substance, a hole transporting substance, a light emitting substance, an electron blocking substance, an electron transporting substance, an electron injecting substance, etc., are backed by stable and effective materials, and thus there is a continuous demand for development of new materials.

[0008] Prior Art Documents

[0009] Patent Documents

[0010] (Patent Document 1) International Patent Publication No. 2017-126443 SUMMARY

[0011] Technical Problem

[0012] A compound and an organic light emitting device including the same are described in the present specification.

[0013] Solution to Problem

[0014] One embodiment of the present specification provides a compound of the following Chemical Formula 1.

[0015] [Chemical Formula 1]

[0016]

[0017] [Chemical Formula 2]

[0018]

[0019] In the above Chemical Formula 1,

[0020] X1 to X3 are the same as or different from each other, each independently N or CR, and two or more of X1 to X3 are N,

[0021] The above 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,

[0022] Ar1 and Ar2 are the same as or different from each other, 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,

[0023] Ar3is the above Chemical Formula 2 substituted with 1 or more cyano groups and can be further substituted with deuterium,

[0024] R1and R2are the same as or different from each other, and each is independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 30,

[0025] HAr is a triazine group substituted with or without 2 substituents each independently selected from the group consisting of deuterium, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 60, and a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 60; a pyrimidine group substituted with or without 1 to 3 substituents each independently selected from the group consisting of deuterium, a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 60, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 60, and a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 60; a quinazoline group substituted with or without 1 substituent selected from the group consisting of deuterium, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 60, and a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 60; a benzo-thieno-pyrimidine group substituted with or without 1 substituent selected from the group consisting of deuterium, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 60, and a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 60; or a benzo-furo-pyrimidine group substituted with or without 1 substituent selected from the group consisting of deuterium, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 60, and a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 60,

[0026] n is an integer of 1 to 4,

[0027] m is an integer of 1 to 3,

[0028] when n is 2 or more, R1is the same as or different from each other,

[0029] when m is 2 or more, R2is the same as or different from each other,

[0030] in the above Chemical Formula 2,

[0031] * is a site combined with Chemical Formula 1,

[0032] a is 0 or 1,

[0033] b is 0 or 1.

[0034] In addition, according to an embodiment of the present application, there is provided an organic light emitting device, wherein, comprising a first electrode, a second electrode, and one or more organic layers disposed between the first electrode and the second electrode, one or more of the organic layers comprising the above compound.

[0035] Effects of the Invention

[0036] The compound of the present application can be used as a material for an organic layer of an organic light emitting device. When an organic light emitting device is manufactured including the compound of the present application, an organic light emitting device having high efficiency, low voltage and long life characteristics can be obtained, and when the compound of the present application is included in an electron transport layer of an organic light emitting device, the compound has high intramolecular polarizability and good electron transfer effect, so that an organic light emitting device having long life characteristics can be manufactured.

[0037] The organic light emitting device of the present application is characterized by including a compound represented by Chemical Formula 1 and a compound represented by Chemical Formula 2. At this time, the compound of the present application substitutes a linking group between two heterocyclic groups in para and meta directions, has a suitable energy barrier of the LUMO orbital energy level of -2.8 to -3.2 eV, has high planarity of the material, maximizes electron mobility, thereby showing high efficiency characteristics, and substitutes a cyano group having excellent polarizability, thereby maintaining long life characteristics. BRIEF DESCRIPTION OF DRAWINGS

[0038] Figures 1 to 3 FIG. 1 illustrates an example of an organic light emitting device according to the present application.

[0039] [Explanation of Symbols]

[0040] 1: Substrate

[0041] 2: Anode

[0042] 3: Organic layer

[0043] 4: Cathode

[0044] 5: Hole injection layer

[0045] 6: Hole transport layer

[0046] 6-1: First hole transport layer

[0047] 6-2: Second hole transport layer

[0048] 7: Electron blocking layer

[0049] 8: Emission layer

[0050] 9: Electron injection and transport layer DETAILED DESCRIPTION

[0051] Hereinafter, the present specification will be described in more detail.

[0052] In the present specification, when a certain part is referred to as "including / including" a certain component, unless otherwise specifically noted, it means that other components can be further included, rather than excluding other components.

[0053] In the present specification, when it is stated that a certain member is positioned "on" another member, it includes not only the case where a certain member is in contact with another member, but also the case where other members are present between the two members.

[0054] In the present specification, "dotted line (— ) " indicates the position of bonding to a chemical formula or a compound.

[0055] In the present specification, the deuterium substitution rate of a compound can be grasped by a method of using TLC-MS (Thin-Layer Chromatography / Mass Spectrometry) and calculating the substitution rate based on the maximum (max.) value of the distribution of molecular weights at the end of the reaction, or by a quantitative analysis method using NMR, adding DMF as an internal standard, and using 1 A method of calculating the D-substitution rate from the integration ratio on H NMR based on the integrated amount of the total peak.

[0056] In the present specification, "X% deuterated", "X% degree of deuteration", or "X% deuterium substitution rate" means that X% of the hydrogens at the substitutable positions in the structure are substituted with deuterium.

[0057] In the present specification, the hydrogens in the structure that can be substituted with deuterium can be substituted with deuterium at more than 0% and 100% or less, 0.1% or more and 99.99% or less, or 100%. For example, when the structure is dibenzofuran, "25% deuterated" dibenzofuran, "25% degree of deuteration" of dibenzofuran, or "25% deuterium substitution rate" of dibenzofuran means that 2 of the 8 hydrogens at the substitutable positions in dibenzofuran are substituted with deuterium, and "50% deuterium substitution rate" can mean that 4 of the 8 hydrogens at the substitutable positions in dibenzofuran are substituted with deuterium.

[0058] The term "substituted" above means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited as long as it is a position where a hydrogen atom can be substituted, i.e., a position where a substituent can be substituted, and when 2 or more are substituted, the 2 or more substituents can be the same as or different from each other.

[0059] In the present specification, the term "substituted or unsubstituted" means that a substituent is selected from 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 alkylthio group Arylthio group Alkylsulfonyl group Arylsulfonyl group one or two or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkoxy group, an aryloxy group, an alkyl group, an aryl group, and a heterocyclic group, or a substituent formed by linking two or more substituents exemplified above, or no substituent. For example, the "substituent formed by linking two or more substituents" can be a biphenyl group. That is, the biphenyl group can be an aryl group, or can be interpreted as a substituent formed by linking two phenyl groups.

[0060] In the present specification, the term "substituted or unsubstituted" means substituted with one or two or more substituents selected from the group consisting of deuterium, a halogen group, a cyano group, a silyl group, an alkoxy group, an aryloxy group, an alkyl group, an aryl group, and a heterocyclic group, or a substituent formed by linking two or more substituents exemplified above, or no substituent.

[0061] In the present specification, the term "substituted or unsubstituted" means substituted with one or two or more substituents selected from the group consisting of deuterium, an alkyl group, an aryl group, and a heterocyclic group, or a substituent formed by linking two or more substituents exemplified above, or no substituent.

[0062] In the present specification, linking of two or more substituents means linking of a hydrogen of any one substituent with another substituent. For example, it can be linking of an isopropyl group with a phenyl group to form such a substituent.

[0063] In the present specification, linking of three substituents includes not only linking of (substituent 1) - (substituent 2) - (substituent 3) successively, but also linking of (substituent 1) with (substituent 2) and (substituent 3). For example, linking of two phenyl groups and an isopropyl group can form such a substituent. Linking of four or more substituents is similarly applicable to the above definition.

[0064] Examples of the above substituents are described below, but are not limited thereto.

[0065] In the present specification, examples of the halogen group are fluorine (-F), chlorine (-Cl), bromine (-Br), or iodine (-I).

[0066] In the present specification, the silyl group can be represented by the chemical formula of -SiYaYbYc, and each of Ya, Yb, and Yc can be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The silyl group is specifically trimethylsilyl, triethylsilyl, t-butyldimethylsilyl, vinyl dimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl, phenylsilyl, or the like, but is not limited thereto.

[0067] In the present specification, a boron group can be represented by the chemical formula of -BYdYe, each of Ydand Ye can be hydrogen, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group. The boron group is specifically, but not limited to, a dimethylboron group, a diethylboron group, a tert-butylmethylboron group, a diphenylboron group, a phenylboron group, and the like.

[0068] In the present specification, the alkyl group can be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the number of carbon atoms of the alkyl group is 1 to 30. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 20. According to another embodiment, the number of carbon atoms of the alkyl group is 1 to 10. As specific examples of the alkyl group, there are 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, and the like, but are not limited thereto.

[0069] In the present specification, the arylalkyl group, in addition to being substituted by an aryl group, can be applicable to the above-described description regarding the alkyl group.

[0070] In the present specification, the alkoxy group can be linear, branched, or cyclic. The number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20. Specifically, it can be a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an isopropyl group, an n-butoxy group, an isobutoxy group, a tert-butoxy group, a sec-butoxy group, an n-pentoxy group, a neopentoxy group, an iso-pentoxy group, an n-hexoxy group, a 3,3-dimethylbutoxy group, a 2-ethylbutoxy group, an n-octoxy group, an n-nonoxy group, an n-decoxy group, and the like, but is not limited thereto.

[0071] The alkyl group, the alkoxy group, and the substituent containing an alkyl moiety other than the above described in the present specification include both linear and branched forms.

[0072] In the present specification, the alkenyl group can be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the number of carbon atoms of the alkenyl group is 2 to 20. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 10. According to another embodiment, the number of carbon atoms of the alkenyl group is 2 to 6. As specific examples, there are an ethenyl group, a 1-propenyl group, an isopropenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 3-methyl-1-butenyl group, a 1,3-butanedienyl group, an allyl group, a 1-phenylethen-1-yl group, a 2-phenylethen-1-yl group, a 2,2-diphenylethen-1-yl group, a 2-phenyl-2-(naphthalen-1-yl)ethen-1-yl group, a 2,2-bis(diphen-1-yl)ethen-1-yl group, a stilbenyl group, a styryl group, and the like, but are not limited thereto.

[0073] In this specification, the alkynyl group is a substituent containing a triple bond between carbon atoms, and can be straight-chain or branched. The number of carbon atoms is not particularly limited, but is preferably 2 to 40. According to one embodiment, the alkynyl group has 2 to 20 carbon atoms. According to another embodiment, the alkynyl group has 2 to 10 carbon atoms.

[0074] In this specification, the cycloalkyl group is not particularly limited, but is preferably a cycloalkyl group with 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to yet another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, etc., are used, but are not limited to these.

[0075] In this specification, the amino group is -NH2, and the amino group may be substituted with alkyl, aryl, heterocyclic, alkenyl, cycloalkyl, or combinations thereof. The number of carbon atoms in the substituted amino group is not particularly limited, but is preferably 1 to 30. According to one embodiment, the number of carbon atoms in the amino group is 1 to 20. According to another embodiment, the number of carbon atoms in the amino group is 1 to 10. Specific examples of the substituted amino group include methylamino, dimethylamino, ethylamino, diethylamino, phenylamino, 9,9-dimethylfluorenylphenylamino, pyridylphenylamino, diphenylamino, phenylpyridylamino, naphthylamino, biphenylamino, anthraceneamino, dibenzofuranylphenylamino, 9-methylanthraylamino, diphenylamino, phenylnaphthylamino, xylylamino, phenyltolylamino, diphenylamino, etc., but are not limited to these.

[0076] In this specification, the aryl group is not particularly limited, but is preferably an aryl group with 6 to 60 carbon atoms, and can be a monocyclic aryl or a polycyclic aryl. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to another embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group can be an aryl group composed of a monocyclic ring or a polycyclic aryl group (an aryl group with two or more rings). An aryl group composed of a monocyclic ring can refer to a phenyl group, or a group formed by two or more phenyl groups linked together. As an aryl group composed of the above-mentioned monocyclic ring, it can be phenyl, biphenyl, terphenyl, tetraphenyl, etc., but is not limited to these. A polycyclic aryl group can refer to a group formed by two or more monocyclic rings fused together, such as naphthyl or phenanthryl. As a polycyclic aryl group, it can be naphthyl, anthraceneyl, phenanthryl, pyrene, perylene, etc. It includes methyl, fluorene, triphenylene, etc., but is not limited to these.

[0077] In this specification, the fluorene group can be substituted, and two substituents can combine with each other to form a spirostructure.

[0078] In the case where the fluorenyl group is substituted, it can be isoindolyl group, and the like. (9,9-dimethylfluorenyl) group, and (9,9-diphenylfluorenyl) group, and the like. However, it is not limited thereto.

[0079] In the present specification, the aryl group in the aryloxy group can be applied to the above-described explanation about the aryl group.

[0080] In the present specification, the heterocyclic group is a ring group including 1 or more heteroatoms selected from N, O, P, S, Si, and Se, and the number of carbon atoms is not particularly limited, but preferably 2 to 60. According to one embodiment, the number of carbon atoms of the above-described heterocyclic group is 2 to 30. According to one embodiment, the number of carbon atoms of the above-described heterocyclic group is 2 to 20. As examples of the heterocyclic group, there are a pyridyl group, a pyrrolyl group, a pyrimidinyl group, a quinolyl group, a pyridazinyl group, a furanyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a benzonaphthothiophenyl group, an indolocarbazolyl group, a triazinyl group, and the like, but not limited thereto.

[0081] In the present specification, the heteroaryl group is aromatic, and the above-described explanation about the heterocyclic group can be applied except for this.

[0082] In the present specification, the heteroaryl group includes 1 or more non-carbon atoms, i.e., heteroatoms, and specifically, the above-described heteroatoms can include 1 or more atoms selected from O, N, Se, and S, and the like. The number of carbon atoms is not particularly limited, but preferably 2 to 30, and the above-described heteroaryl group can be a monocyclic or polycyclic ring. As examples of the heteroaryl group, there are a thienyl group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, oxazolyl group, oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidinyl group, a triazinyl group, a triazolyl group, an acridyl group, a pyridazinyl group, a pyrazinyl group, a quinolyl group, a quinazolyl group, a quinoxalyl group, a phthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a pyrazinopyrazinyl group, an isoquinolyl group, an indolyl group, a carbazolyl group, a benz oxazolyl group, a benzimidazolyl group, a benzothiazolyl group, a benzocarbazolyl group, a benzothiophenyl group, a dibenzothiophenyl group, a benzofuranyl group, a phenanthridine group, a phenanthroline group, an iso oxadiazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a phen oxathiine group, a phen oxazine group, a phenothiazine group, a dihydroindenocarbazolyl group, a spirofluorene xanthene group, and a spirofluorene thioxanthene group, and the like, but not limited thereto.

[0083] In the present specification, the above-mentioned aryl group, except for being divalent, can be applied to the above-mentioned aryl group.

[0084] In the present specification, the above-mentioned heterocyclic group, except for being divalent, can be applied to the above-mentioned heterocyclic group.

[0085] In the present specification, the above-mentioned aryl group, except for being n+1 valent, can be applied to the above-mentioned aryl group.

[0086] In the present specification, the above-mentioned heterocyclic group, except for being n+1 valent, can be applied to the above-mentioned heterocyclic group.

[0087] In the present specification, in a substituted or unsubstituted ring formed by adjacent groups combining with each other, "ring" means a hydrocarbon ring or a heterocyclic ring.

[0088] The above-mentioned hydrocarbon ring can be an aromatic, aliphatic, or aromatic and aliphatic fused ring, and can be selected from the above-mentioned examples of cycloalkyl or aryl groups.

[0089] In the present specification, the meaning of a ring formed by adjacent groups combining with each other means a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocyclic ring; a substituted or unsubstituted aromatic heterocyclic ring; or a fused ring thereof. The above-mentioned hydrocarbon ring means a ring composed of only carbon and hydrogen atoms. The above-mentioned heterocyclic ring means a ring containing 1 or more selected from N, O, P, S, Si, and Se. In the present specification, the above-mentioned aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic heterocyclic ring, and aromatic heterocyclic ring can be a single ring or a multiple ring.

[0090] In the present specification, the aliphatic hydrocarbon ring means a ring composed of only carbon and hydrogen atoms, which is not aromatic. As examples of the aliphatic hydrocarbon ring, there are cyclopropane, cyclobutane, cyclobutene, cyclopentane, cyclopentene, cyclohexane, cyclohexene, 1,4-cyclohexadiene, cycloheptane, cycloheptene, cyclooctane, cyclooctene, and the like, but are not limited thereto.

[0091] In the present specification, the aromatic hydrocarbon ring means an aromatic ring composed of only carbon and hydrogen atoms. As examples of the aromatic hydrocarbon ring, there are benzene, naphthalene, anthracene, phenanthrene, perylene, fluoranthene, triphenylene, phenalene, pyrene, tetracene, , pentacene, fluorene, indene, acenaphthylene, benzofluorene, spirofluorene, and the like, but are not limited thereto. In the present specification, the aromatic hydrocarbon ring can be interpreted as having the same meaning as the aryl group.

[0092] In the present specification, the aliphatic heterocyclic ring means an aliphatic ring containing 1 or more heteroatoms. As examples of the aliphatic heterocyclic ring, there are oxirane, tetrahydrofuran, 1,4-dioxane, pyrrolidine, pyrroline, pyrrole, imidazolidine, imidazoline, imidazole, triazole, tetrazole, oxazole, isoxazole, isoxazine, furan, thiophene, pyran, selenaphene, pyridine, piperidine, piperazine, morpholine, indole, isoindole, benzofuran, benzothiophene, benzopyran, benzoxazine, and the like, but are not limited thereto. alkane, 1,4-dioxane, pyrrolidine, piperidine, morpholine, oxepane azepane thiepane etc., but are not limited thereto.

[0093] In the present specification, an aromatic heterocycle refers to an aromatic ring including one or more heteroatoms. Examples of the aromatic heterocycle include pyridine, pyrrole, pyrimidine, pyridazine, furan, thiophene, imidazole, pyrazole, oxazole, isoxazole, thiazole, isothiazole, triazole, diazole, thiadiazole, dithiazole, tetrazole, pyran, thiapyran, diazine, oxazine, thiazine, diazine, triazine, tetrazine, isoquinoline, quinoline, quinone, quinazoline, quinoxaline, naphthylidine, acridine, phenanthridine, perimidine, indole, indolizine, benzothiazole, benzimidazole, benzothiophene, benzofuran, dibenzothiophene, dibenzofuran, carbazole, benzocarbazole, dibenzocarbazole, phenoxazine, imidazopyridine, phen azin, indolocarbazole, indolocarbazole, and the like, but are not limited thereto.

[0094] In the present specification, a fused ring refers to a ring structure in which two or more rings share two or more atoms. The above-mentioned fused ring can be a fused ring of an aromatic hydrocarbon ring, an aliphatic hydrocarbon ring, or an aromatic hydrocarbon ring and an aliphatic hydrocarbon ring, but is not limited thereto.

[0095] In the present specification, a fused aromatic hydrocarbon ring group refers to a ring in which two or more aromatic hydrocarbon rings are fused. Examples of the fused aromatic hydrocarbon ring group can be naphthyl, anthryl, phenanthryl, pyrenyl, perylenyl, fluorenyl, triphenylenyl etc., but are not limited thereto.

[0096] In the present specification, unless defined otherwise, all the technical and scientific terms used in the present specification have the same meanings as those generally understood by one of ordinary skill in the art. Methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present application, but a later-described method and material is preferred. All publications, patent applications, patents and other references mentioned in the present specification are incorporated by reference in their entirety into the present specification, in the event of a conflict between the present specification and the incorporated references, the present specification controls, including the definition of terms. In addition, the materials, methods, and examples are illustrative only and not intended to be limiting.

[0097] In the present specification, the position of Formula 1 which can be substituted with hydrogen can be substituted with deuterium.

[0098] In the present specification, the position of Formula 2 which can be substituted with hydrogen can be substituted with deuterium.

[0099] In the present specification, HAr of Formula 1 can be triazinyl which is substituted or unsubstituted with 2 substituents each independently selected from the group consisting of deuterium, 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; pyrimidinyl which is substituted or unsubstituted with 1 to 3 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; quinazolinyl which is substituted or unsubstituted with 1 substituent selected from the group consisting of deuterium, 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; benzothienopyrimidinyl which is substituted or unsubstituted with 1 substituent selected from the group consisting of deuterium, 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 benzofuranopyrimidinyl which is substituted or unsubstituted with 1 substituent selected from the group consisting of deuterium, 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 the position of Formula 1 which can be substituted with hydrogen in the triazinyl, pyrimidinyl, quinazolinyl, benzothienopyrimidinyl, or benzofuranopyrimidinyl can be substituted with deuterium.

[0100] In the present specification, HAr of the above formula 1 is triazinyl substituted with 2 substituents each independently selected from the group consisting of deuterium, 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; pyrimidinyl substituted with 1 to 3 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; quinazolinyl substituted with 1 substituent selected from the group consisting of deuterium, 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; benzo-thienopyrimidinyl substituted with 1 substituent selected from the group consisting of deuterium, 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 benzo-furo-pyrimidinyl substituted with 1 substituent selected from the group consisting of deuterium, 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.

[0101] According to an embodiment of the present specification, HAr is triazinyl substituted with 2 substituents each independently selected from the group consisting of deuterium, 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; pyrimidinyl substituted with 1 to 3 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; quinazolinyl substituted with 1 substituent selected from the group consisting of deuterium, 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; benzo-thienopyrimidinyl substituted with 1 substituent selected from the group consisting of deuterium, 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 benzo-furo-pyrimidinyl substituted with 1 substituent selected from the group consisting of deuterium, 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.

[0102] According to an embodiment of the present specification, the above HAr is triazinyl substituted or unsubstituted with 2 substituents each independently selected from the group consisting of deuterium, 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; pyrimidinyl substituted or unsubstituted with 1 to 3 substituents each independently selected from the group consisting of 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; quinazolinyl substituted or unsubstituted with 1 substituent selected from the group consisting of deuterium, 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; benzothienopyrimidinyl substituted or unsubstituted with 1 substituent selected from the group consisting of deuterium, 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 benzofuranopyrimidinyl substituted or unsubstituted with 1 substituent selected from the group consisting of deuterium, 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.

[0103] According to an embodiment of the present specification, the above HAr is triazinyl substituted or unsubstituted with 2 substituents each independently selected from the group consisting of deuterium, 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; pyrimidinyl substituted or unsubstituted with 1 to 3 substituents each independently selected from the group consisting of 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; quinazolinyl substituted or unsubstituted with 1 substituent selected from the group consisting of deuterium, 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; benzothienopyrimidinyl substituted or unsubstituted with 1 substituent selected from the group consisting of deuterium, 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 benzofuranopyrimidinyl substituted or unsubstituted with 1 substituent selected from the group consisting of deuterium, 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.

[0104] According to an embodiment of the present specification, the above HAr is triazinyl substituted or unsubstituted with 2 substituents each independently selected from the group consisting of deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted pyrimidinyl; pyrimidinyl substituted or unsubstituted with 1 to 3 substituents each independently selected from the group consisting of deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted propyl, and substituted or unsubstituted pyridyl; quinazolinyl substituted or unsubstituted with 1 substituent selected from the group consisting of deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted pyridyl; benzothienopyrimidinyl substituted or unsubstituted with 1 substituent selected from the group consisting of deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted pyridyl; or benzofuranopyrimidinyl substituted or unsubstituted with 1 substituent selected from the group consisting of deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, and substituted or unsubstituted pyridyl.

[0105] According to an embodiment of the present specification, the above HAr is triazinyl substituted or unsubstituted with 2 substituents each independently selected from the group consisting of deuterium, deuterium- or alkyl-substituted or unsubstituted phenyl, deuterium- or alkyl-substituted or unsubstituted biphenyl, deuterium- or alkyl-substituted or unsubstituted naphthyl, and deuterium- or alkyl-substituted or unsubstituted pyrimidinyl; pyrimidinyl substituted or unsubstituted with 1 to 3 substituents each independently selected from the group consisting of deuterium, deuterium- or alkyl-substituted or unsubstituted phenyl, deuterium- or alkyl-substituted or unsubstituted biphenyl, deuterium- or alkyl-substituted or unsubstituted naphthyl, deuterium- or alkyl-substituted or unsubstituted methyl, deuterium- or alkyl-substituted or unsubstituted ethyl, deuterium- or alkyl-substituted or unsubstituted propyl, and deuterium- or alkyl-substituted or unsubstituted pyridyl; quinazolinyl substituted or unsubstituted with 1 substituent selected from the group consisting of deuterium, deuterium- or alkyl-substituted or unsubstituted phenyl, deuterium- or alkyl-substituted or unsubstituted biphenyl, deuterium- or alkyl-substituted or unsubstituted naphthyl, and deuterium- or alkyl-substituted or unsubstituted pyridyl; benzothienopyrimidinyl substituted or unsubstituted with 1 substituent selected from the group consisting of deuterium, deuterium- or alkyl-substituted or unsubstituted phenyl, deuterium- or alkyl-substituted or unsubstituted biphenyl, deuterium- or alkyl-substituted or unsubstituted naphthyl, and deuterium- or alkyl-substituted or unsubstituted pyridyl; or benzofuranopyrimidinyl substituted or unsubstituted with 1 substituent selected from the group consisting of deuterium, deuterium- or alkyl-substituted or unsubstituted phenyl, deuterium- or alkyl-substituted or unsubstituted biphenyl, deuterium- or alkyl-substituted or unsubstituted naphthyl, and deuterium- or alkyl-substituted or unsubstituted pyridyl.

[0106] In one embodiment of the present specification, the above R is hydrogen, deuterium, a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 10, or a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30.

[0107] In one embodiment of the present specification, the above R is hydrogen or deuterium.

[0108] According to one embodiment of the present specification, the above R1and R2are the same as or different from each other, and each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 30.

[0109] According to one embodiment of the present specification, the above R1and R2are the same as or different from each other, and each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 20.

[0110] According to one embodiment of the present specification, the above R1and R2are the same as or different from each other, and each independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 10.

[0111] According to one embodiment of the present specification, the above R1and R2are the same as or different from each other, and each independently hydrogen or deuterium.

[0112] According to one embodiment of the present specification, the above R1and R2are both hydrogen.

[0113] According to one embodiment of the present specification, the above R1and R2are both deuterium.

[0114] In the present specification, the above Chemical Formula 1 is any one of the following Chemical Formulae 1-1 to 1-5.

[0115] [Chemical Formula 1-1]

[0116]

[0117] [Chemical Formula 1-2]

[0118]

[0119] [Chemical Formula 1-3]

[0120]

[0121] [Chemical Formula 1-4]

[0122]

[0123] [Chemical Formula 1-5]

[0124]

[0125] In the above Chemical Formulae 1-1 to 1-5,

[0126] X1to X3, Ar1to Ar3, n, and m are the same as the definitions in Chemical Formula 1 above,

[0127] R1and R2are the same as or different from each other, and each is independently hydrogen or deuterium,

[0128] R3and R4are the same as or different from each other, and each is independently deuterium, 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,

[0129] R5is hydrogen, 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,

[0130] R6is deuterium, 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,

[0131] o is an integer of 1 to 3,

[0132] When o is 2 or more, R5is the same as or different from each other.

[0133] In the present specification, the above Chemical Formula 1 is Chemical Formula 1-1 above.

[0134] In the present specification, the above Chemical Formula 1 is Chemical Formula 1-2 above.

[0135] In the present specification, the above Chemical Formula 1 is Chemical Formula 1-3 above.

[0136] In the present specification, the above Chemical Formula 1 is Chemical Formula 1-4 above.

[0137] In the present specification, the above Chemical Formula 1 is Chemical Formula 1-5 above.

[0138] According to an embodiment of the present specification, X1to X3are the same as or different from each other, and each is independently N or CR, and two or more of X1to X3are N.

[0139] In an embodiment of the present specification, two or more of X1to X3are N.

[0140] In an embodiment of the present specification, X1and X2are N.

[0141] In an embodiment of the present specification, X1and X3are N.

[0142] In an embodiment of the present specification, X2and X3are N.

[0143] In one embodiment of the present specification, X1to X3are each N.

[0144] According to one embodiment of the present specification, Ar1and Ar2are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having a carbon atom number of 6 to 60, or a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 60.

[0145] According to one embodiment of the present specification, Ar1and Ar2are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30, or a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 30.

[0146] According to one embodiment of the present specification, Ar1and Ar2are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having a carbon atom number of 6 to 20, or a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 20.

[0147] According to one embodiment of the present specification, Ar1and Ar2are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidyl group, or a substituted or unsubstituted quinazoline group.

[0148] According to one embodiment of the present specification, Ar1and Ar2are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group substituted or unsubstituted with deuterium, an alkyl group having a carbon atom number of 1 to 10, or an aryl group having a carbon atom number of 6 to 20; a substituted or unsubstituted naphthyl group substituted or unsubstituted with deuterium, an alkyl group having a carbon atom number of 1 to 10, or an aryl group having a carbon atom number of 6 to 20; a substituted or unsubstituted pyridyl group substituted or unsubstituted with deuterium, an alkyl group having a carbon atom number of 1 to 10, or an aryl group having a carbon atom number of 6 to 20; a substituted or unsubstituted pyrimidyl group substituted or unsubstituted with deuterium, an alkyl group having a carbon atom number of 1 to 10, or an aryl group having a carbon atom number of 6 to 20; or a substituted or unsubstituted quinazoline group substituted or unsubstituted with deuterium, an alkyl group having a carbon atom number of 1 to 10, or an aryl group having a carbon atom number of 6 to 20.

[0149] According to one embodiment of the present specification, Ar3is the above formula 2 substituted with one or more cyano groups, and can be further substituted with deuterium.

[0150] According to one embodiment of the present specification, Ar3is the above formula 2 substituted with one cyano group, and can be further substituted with deuterium.

[0151] According to one embodiment of the present specification, Ar3is the above formula 2 substituted with two cyano groups, and can be further substituted with deuterium.

[0152] According to an embodiment of the present specification, the above-described Ar3 is the above-described Chemical Formula 2 which is substituted with one or two cyano groups and can be further substituted with deuterium.

[0153] According to an embodiment of the present specification, the above-described Ar3 is the above-described Chemical Formula 2 which is not substituted with three cyano groups and can be further substituted with deuterium.

[0154] According to an embodiment of the present specification, the above-described Ar3 is represented by any one of the following structural formulas.

[0155]

[0156]

[0157] The above-described structural formula can be substituted with deuterium or not substituted with deuterium,

[0158] In the above-described structural formula, the dotted line indicates a bonding position.

[0159] According to an embodiment of the present specification, the above-described Chemical Formula 1 is any one of the following Chemical Formula 1-A to Chemical Formula 1-D.

[0160] [Chemical Formula 1-A]

[0161]

[0162] [Chemical Formula 1-B]

[0163]

[0164] [Chemical Formula 1-C]

[0165]

[0166] [Chemical Formula 1-D]

[0167]

[0168] In the above-described Chemical Formula 1-A to Chemical Formula 1-D,

[0169] X1 to X3, Ar1 to Ar3, n, m, and HAr are the same as defined in the above-described Chemical Formula 1, R1 and R2 are the same as or different from each other, and each is independently hydrogen or deuterium.

[0170] According to an embodiment of the present specification, the above-described Chemical Formula 1-3 is the following Chemical Formula 1-3-1 or Chemical Formula 1-3-2.

[0171] [Chemical Formula 1-3-1]

[0172]

[0173] [Chemical Formula 1-3-2]

[0174]

[0175] In the above Chemical Formula 1-3-1 and Chemical Formula 1-3-2,

[0176] X1to X3, Ar1to Ar3, n, m, R1, R2, and R6are the same as the definitions in the above Chemical Formula 1-3.

[0177] According to an embodiment of the present specification, the above Chemical Formula 1-4 is the following Chemical Formula 1-4-1 or Chemical Formula 1-4-2.

[0178] [Chemical Formula 1-4-1]

[0179]

[0180] [Chemical Formula 1-4-2]

[0181]

[0182] In the above Chemical Formula 1-4-1 and Chemical Formula 1-4-2,

[0183] X1to X3, Ar1to Ar3, n, m, R1, R2, and R6are the same as the definitions in the above Chemical Formula 1-4.

[0184] According to an embodiment of the present specification, the above Chemical Formula 1-5 is the following Chemical Formula 1-5-1 or Chemical Formula 1-5-2.

[0185] [Chemical Formula 1-5-1]

[0186]

[0187] [Chemical Formula 1-5-2]

[0188]

[0189] In the above Chemical Formula 1-5-1 and Chemical Formula 1-5-2,

[0190] X1to X3, Ar1to Ar3, n, m, R1, R2, and R6are the same as the definitions in the above Chemical Formula 1-5.

[0191] In the present specification, the above Chemical Formula 1-3 is the above Chemical Formula 1-3-1.

[0192] In the present specification, the above Chemical Formula 1-3 is the above Chemical Formula 1-3-2.

[0193] In the present specification, the above Chemical Formula 1-4 is the above Chemical Formula 1-4-1.

[0194] In the present specification, the above Chemical Formula 1-4 is Chemical Formula 1-4-2 above.

[0195] In the present specification, the above Chemical Formula 1-5 is Chemical Formula 1-5-1 above.

[0196] In the present specification, the above Chemical Formula 1-5 is Chemical Formula 1-5-2 above.

[0197] According to one embodiment of the present specification, the above R3and R4are the same as or different from each other, and each is independently deuterium, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 60, or a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 60.

[0198] According to one embodiment of the present specification, the above R3and R4are the same as or different from each other, and each is independently deuterium, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30, or a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 30.

[0199] According to one embodiment of the present specification, the above R3and R4are the same as or different from each other, and each is independently deuterium, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 20, or a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 20.

[0200] According to one embodiment of the present specification, the above R3and R4are the same as or different from each other, and each is independently deuterium, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 10, or a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 10.

[0201] According to one embodiment of the present specification, the above R3and R4are the same as or different from each other, and each is independently deuterium, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted pyridyl group.

[0202] According to one embodiment of the present specification, the above R3and R4are the same as or different from each other, and each is independently deuterium; a phenyl group substituted or unsubstituted with deuterium, a methyl group, or a pyrimidyl group; a biphenyl group substituted or unsubstituted with deuterium, a methyl group, or a pyrimidyl group; a naphthyl group substituted or unsubstituted with deuterium, a methyl group, or a pyrimidyl group; or a pyridyl group substituted or unsubstituted with deuterium, a methyl group, or a pyrimidyl group.

[0203] According to one embodiment of the present specification, the above R3and R4are the same as or different from each other, and each is independently a phenyl group substituted or unsubstituted with deuterium, a methyl group, or a pyrimidyl group; a biphenyl group substituted or unsubstituted with deuterium, a methyl group, a phenyl group, or a pyrimidyl group; a naphthyl group substituted or unsubstituted with deuterium, a methyl group, a phenyl group, or a pyrimidyl group; or a pyridyl group substituted or unsubstituted with deuterium, a methyl group, a phenyl group, or a pyrimidyl group.

[0204] According to an embodiment of the present specification, the above R5is hydrogen, deuterium, a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 60, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 60, or a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 60.

[0205] According to an embodiment of the present specification, the above R5is hydrogen, deuterium, a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 30, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30, or a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 30.

[0206] According to an embodiment of the present specification, the above R5is hydrogen, deuterium, a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 20, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 20, or a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 20.

[0207] According to an embodiment of the present specification, the above R5is hydrogen, deuterium, a substituted or unsubstituted alkyl group having a carbon atom number of 1 to 10, a substituted or unsubstituted aryl group having a carbon atom number of 6 to 10, or a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 10.

[0208] According to an embodiment of the present specification, the above R5is hydrogen, deuterium, a methyl group, an ethyl group, a propyl group, an isopropyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted pyridyl group.

[0209] According to an embodiment of the present specification, the above R5is hydrogen; deuterium; a methyl group; an ethyl group; a propyl group; an isopropyl group; a phenyl group substituted or unsubstituted with deuterium, an alkyl group, an aryl group, or a heteroaryl group; a biphenyl group substituted or unsubstituted with deuterium, an alkyl group, an aryl group, or a heteroaryl group; a naphthyl group substituted or unsubstituted with deuterium, an alkyl group, an aryl group, or a heteroaryl group; or a pyridyl group substituted or unsubstituted with deuterium, an alkyl group, an aryl group, or a heteroaryl group.

[0210] According to an embodiment of the present specification, the above R5is hydrogen; deuterium; a methyl group; an ethyl group; a propyl group; an isopropyl group; a phenyl group substituted or unsubstituted with deuterium, an alkyl group, an aryl group, or a heteroaryl group; a biphenyl group substituted or unsubstituted with deuterium, a methyl group, an ethyl group, a phenyl group, or a pyridyl group; a naphthyl group substituted or unsubstituted with deuterium, a methyl group, an ethyl group, a phenyl group, or a pyridyl group; or a pyridyl group substituted or unsubstituted with deuterium, a methyl group, an ethyl group, a phenyl group, or a pyridyl group.

[0211] According to an embodiment of the present specification, the above R6is a substituted or unsubstituted aryl group having a carbon atom number of 6 to 60, or a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 60.

[0212] According to an embodiment of the present specification, the above R6is a substituted or unsubstituted aryl group having a carbon atom number of 6 to 30, or a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 30.

[0213] According to an embodiment of the present specification, the above R6is a substituted or unsubstituted aryl group having a carbon atom number of 6 to 20, or a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 20.

[0214] According to an embodiment of the present specification, the above R6is a substituted or unsubstituted aryl group having a carbon atom number of 6 to 10, or a substituted or unsubstituted heteroaryl group having a carbon atom number of 2 to 10.

[0215] According to an embodiment of the present specification, the above R6is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted pyridyl group.

[0216] According to an embodiment of the present specification, the above R6is a phenyl group substituted or unsubstituted with deuterium or an alkyl group; a biphenyl group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; a naphthyl group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group; or a pyridyl group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group.

[0217] According to an embodiment of the present specification, the above R6is a phenyl group substituted or unsubstituted with deuterium, an alkyl group, a phenyl group, or a pyridyl group; a biphenyl group substituted or unsubstituted with deuterium, a methyl group, an ethyl group, a phenyl group, or a pyridyl group; a naphthyl group substituted or unsubstituted with deuterium, a methyl group, an ethyl group, a phenyl group, or a pyridyl group; or a pyridyl group substituted or unsubstituted with deuterium, a methyl group, an ethyl group, a phenyl group, or a pyridyl group.

[0218] According to an embodiment of the present specification, the above n is an integer of 1 to 4.

[0219] According to an embodiment of the present specification, the above n is 1.

[0220] According to an embodiment of the present specification, the above n is 2.

[0221] According to an embodiment of the present specification, the above n is 3.

[0222] According to an embodiment of the present specification, the above n is 4.

[0223] According to an embodiment of the present specification, the above m is an integer of 1 to 3.

[0224] According to an embodiment of the present specification, the above m is 1.

[0225] According to an embodiment of the present specification, the above m is 2.

[0226] According to an embodiment of the present specification, the above m is 3.

[0227] According to an embodiment of the present specification, the above o is an integer of 1 to 3.

[0228] According to an embodiment of the present specification, the above o is 1.

[0229] According to an embodiment of the present specification, the above o is 2.

[0230] According to an embodiment of the present specification, the above o is 3.

[0231] According to an embodiment of the present specification, the above a is 0 or 1.

[0232] According to an embodiment of the present specification, the above a is 0.

[0233] According to an embodiment of the present specification, the above a is 1.

[0234] According to an embodiment of the present specification, the above b is 0 or 1.

[0235] According to an embodiment of the present specification, the above b is 0.

[0236] According to an embodiment of the present specification, the above b is 1.

[0237] According to an embodiment of the present specification, the above Chemical Formula 1 is any one of the following structural formulas.

[0238] According to an embodiment of the present specification, the above Chemical Formula 1 is any one of the following structural formulas, which can be substituted with deuterium or unsubstituted.

[0239]

[0240]

[0241]

[0242]

[0243]

[0244]

[0245]

[0246]

[0247]

[0248] According to an embodiment of the present specification, the above Chemical Formula 1 has a deuterium substitution rate of 30% or more.

[0249] According to an embodiment of the present specification, the above Chemical Formula 1 has a deuterium substitution rate of 40% or more.

[0250] According to an embodiment of the present specification, the deuterium substitution rate of the above chemical formula 1 is 50% or more.

[0251] According to an embodiment of the present specification, the deuterium substitution rate of the above chemical formula 1 is 60% or more.

[0252] According to an embodiment of the present specification, the deuterium substitution rate of the above chemical formula 1 is 70% or more.

[0253] According to an embodiment of the present specification, the deuterium substitution rate of the above chemical formula 1 is 80% or more.

[0254] According to an embodiment of the present specification, the deuterium substitution rate of the above chemical formula 1 is 90% or more.

[0255] According to an embodiment of the present specification, the deuterium substitution rate of the above chemical formula 1 is 100%.

[0256] The substituents of the above chemical formula 1 can be combined by a method known in the art, and the kind, position, or number of the substituents can be changed according to a technique known in the art.

[0257] In addition, by introducing various substituents in the core structure of the structure as described above, a compound having inherent properties of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in a hole injection layer material, a hole transport material, a light emitting layer material, and an electron transport layer material used in the manufacture of an organic light emitting device into the above core structure, a material satisfying the required conditions in each organic layer can be synthesized.

[0258] In addition, the organic light emitting device according to the present application is characterized by comprising a first electrode, a second electrode disposed opposite to the above first electrode, and one or more organic layers disposed between the above first electrode and the above second electrode, one or more of the above organic layers comprising the above-mentioned compound.

[0259] The organic light emitting device of the present application forms one or more organic layers using the above-mentioned compound, and in addition thereto, can be manufactured using the manufacturing method and materials of a general organic light emitting device.

[0260] The above-mentioned compound can be formed into an organic layer using not only a vacuum evaporation method but also a solution coating method when manufacturing an organic light emitting device. Here, the solution coating method refers to a spin coating method, a dip coating method, an inkjet printing method, a screen printing method, a spray method, a roll coating method, etc., but is not limited thereto.

[0261] The organic layer of the organic light emitting device of the present application can be formed of a single layer structure or a multi-layer structure in which two or more organic layers are stacked. For example, the organic light emitting device of the present application can have a structure including a hole injection layer, a hole transport layer, a layer performing both hole injection and hole transport, a light emitting layer, an electron transport layer, an electron injection layer, and the like as the organic layer. However, the structure of the organic light emitting device is not limited thereto and can include a smaller number of organic layers or a larger number of organic layers.

[0262] In the organic light emitting device of the present application, the organic layer can include one or more layers selected from the group consisting of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and one or more layers among the layers can include the compound represented by Chemical Formula 1.

[0263] In another organic light emitting device, the organic layer can include an electron transport layer, an electron injection layer, or an electron injection and transport layer, and the electron transport layer, the electron injection layer, or the electron injection and transport layer can include the compound represented by Chemical Formula 1.

[0264] In the organic light emitting device of the present application, the electron injection and transport layer includes the compound of Chemical Formula 1 and a metal ligand.

[0265] In the organic light emitting device of the present application, the organic layer can include one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, and a layer performing both hole injection and hole transport, and one or more layers among the layers can include the compound represented by Chemical Formula 1.

[0266] In another organic light emitting device, the organic layer can include a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer can include the compound represented by Chemical Formula 1.

[0267] In one embodiment of the present application, the first electrode is an anode and the second electrode is a cathode.

[0268] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0269] (1) Anode / Hole Transport Layer / Light Emitting Layer / Cathode

[0270] (2) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Cathode

[0271] (3) Anode / Hole Injection Layer / Hole Buffer Layer / Hole Transport Layer / Light Emitting Layer / Cathode

[0272] (4) Anode / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Cathode

[0273] (5) anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0274] (6) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0275] (7) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0276] (8) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0277] (9) anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0278] (10) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

[0279] (11) anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0280] (12) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

[0281] (13) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0282] (14) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

[0283] (15) anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0284] (16) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

[0285] (17) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0286] (18) anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / hole blocking layer / electron injection and transport layer / cathode

[0287] (19) anode / hole injection layer / hole transport layer / light emitting layer / electron injection and transport layer / cathode

[0288] (20) anode / hole injection layer / first hole transport layer / second hole transport layer / light emitting layer / electron injection and transport layer / cathode

[0289] The structure of the organic light emitting device of the present application can have a structure as shown in Figures 1 to 3 but is not limited thereto.

[0290] Figure 1 A structure of an organic light emitting device in which an anode 2, an organic layer 3, and a cathode 4 are sequentially stacked on a substrate 1 is exemplified in the above. In the structure as described above, the compound represented by the above formula 1 can be contained in the above organic layer 3.

[0291] Figure 2 A 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 stacked on a substrate 1 is exemplified in the above. The compound represented by the above formula 1 can be contained in the electron injection and transport layer 9.

[0292] Figure 3 A 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 stacked on a substrate 1 is exemplified in the above. The compound represented by the above formula 1 can be contained in the electron injection and transport layer 9.

[0293] For example, the organic light emitting device according to the present application can be manufactured as follows: a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation is used to evaporate a metal or a metal oxide having conductivity or an alloy thereof on a substrate to form an anode, and then an organic layer including 1 layer or more selected from a hole injection layer, a hole transport layer, a layer performing both hole transport and hole injection, a light emitting layer, an electron transport layer, an electron injection layer, and a layer performing both electron transport and electron injection is formed on the anode, and then a substance usable as a cathode is evaporated on the organic layer to manufacture. In addition to this method, an organic light emitting device can also be manufactured by sequentially evaporating a cathode substance, an organic layer, and an anode substance on a substrate.

[0294] The above organic layer can be 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 can also be a single layer structure. In addition, the above organic layer can be manufactured into a smaller number of layers using various polymer materials and by a solvent process other than an evaporation method, such as a spin coating method, a dip coating method, a blade coating method, a screen printing method, an inkjet printing method, or a thermal transfer method.

[0295] The anode is an electrode into which holes are injected. As an anode material, a material having a large work function is generally used in order to allow holes to be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present application include metals such as vanadium, chromium, copper, zinc, gold, and alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO), and the like; combinations of a metal and an oxide such as ZnO:Al or SnO2:Sb; electrically conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, polyaniline, and the like, but are not limited thereto.

[0296] The cathode is an electrode into which electrons are injected. As a cathode material, a material having a small work function is generally used in order to allow electrons to be easily injected into the organic layer. Specific examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, and alloys thereof; multilayered structure materials such as LiF / Al or LiO2 / Al, and the like, but are not limited thereto.

[0297] The hole injection layer is a layer that functions to allow holes to be smoothly injected from the anode to the light-emitting layer. The hole injection material is a material that can receive holes from the anode at a low voltage. The HOMO (highest occupied molecular orbital) of the hole injection material is preferably between the work function of the anode and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic material, hexacyno hexaazatriphenylene-based organic material, quinacridone-based organic material, perylene-based organic material, anthraquinone, and electrically conductive polymers such as polyaniline and polythiophene, but are not limited thereto. The thickness of the hole injection layer can be 1 to 150 nm. When the thickness of the hole injection layer is 1 nm or more, it is possible to prevent a decrease in hole injection characteristics. When the thickness of the hole injection layer is 150 nm or less, it is possible to prevent an increase in driving voltage due to an increase in the mobility of holes when the thickness of the hole injection layer is too thick.

[0298] According to an embodiment of the present specification, the hole injection layer can be a compound of the following formula HI-1.

[0299] [Formula HI-1]

[0300]

[0301] In the above formula HI-1,

[0302] R201to R204are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted ring,

[0303] In an embodiment of the present specification, R201to R204are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or combine with an adjacent group to form a substituted or unsubstituted ring.

[0304] In an embodiment of the present specification, R201to R204are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0305] In an embodiment of the present specification, R201to R204are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0306] In an embodiment of the present specification, R201to R204are the same as or different from each other, and each independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0307] In an embodiment of the present specification, R202and R204are the same as or different from each other, and each independently a substituted or unsubstituted aryl group.

[0308] In an embodiment of the present specification, R201and R203are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0309] In an embodiment of the present specification, R201and R203are the same as or different from each other, and each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0310] In an embodiment of the present specification, R201and R203are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group.

[0311] In an embodiment of the present specification, R202and R204are the same as or different from each other, and each independently a substituted or unsubstituted heteroaryl group.

[0312] In an embodiment of the present specification, R202and R204are the same as or different from each other, and each independently a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0313] In one embodiment of the present specification, R202and R204are the same as or different from each other, and each independently a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.

[0314] In one embodiment of the present specification, R202and R204are the same as or different from each other, and each independently a substituted or unsubstituted carbazolyl group.

[0315] In one embodiment of the present specification, R202and R204are the same as or different from each other, and each independently a substituted or unsubstituted carbazolyl group.

[0316] In one embodiment of the present specification, R202and R204are the same as or different from each other, and each independently a substituted or unsubstituted carbazolyl group.

[0317] In one embodiment of the present specification, the above-described Chemical Formula HI-1 is represented by the following compound.

[0318]

[0319] The above-described hole transport layer can function to smoothly transport holes. The hole transport substance is a substance capable of receiving holes from the anode or the hole injection layer and transferring them to the light-emitting layer, and a substance having a large mobility of holes is suitable. As specific examples, there are arylamine-based organic substances, electrically conductive polymers, and block copolymers in which a conjugated portion and a non-conjugated portion coexist, but are not limited thereto.

[0320] According to one embodiment of the present specification, the above-described hole transport layer contains a compound of the following Chemical Formula HT-1, but is not limited thereto.

[0321] [Chemical Formula HT-1]

[0322]

[0323] In the above-described Chemical Formula HT-1,

[0324] at least one of X'1to X'6is N, and the rest are CH,

[0325] R309to R314are the same as or different from each other, and each independently 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 an adjacent group to form a substituted or unsubstituted ring.

[0326] According to one embodiment of the present specification, the above-described X'1to X'6are N.

[0327] According to an embodiment of the present specification, the above R309 to R314 are cyano.

[0328] According to an embodiment of the present specification, the above chemical formula HT-1 can include the following compounds.

[0329]

[0330] According to an embodiment of the present specification, the above hole transport layer includes a compound represented by the following chemical formula HT-2, but is not limited thereto.

[0331] [Chemical Formula HT-2]

[0332]

[0333] In the above chemical formula HT-2,

[0334] R315 to R317 are the same as or different from each other, and each is independently any 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 a combination thereof, or combine with an adjacent group to form a substituted or unsubstituted ring,

[0335] r315 is an integer of 1 to 5, and when the above r315 is 2 or more, 2 or more of the above R315 are the same as or different from each other,

[0336] r316 is an integer of 1 to 5, and when the above r316 is 2 or more, 2 or more of the above R316 are the same as or different from each other.

[0337] According to an embodiment of the present specification, the above 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.

[0338] According to an embodiment of the present specification, the above R317 is a substituted or unsubstituted phenyl group, or a substituted or unsubstituted fluorenyl group, or adjacent groups combine with each other to form a substituted or unsubstituted ring.

[0339] According to an embodiment of the present specification, the above R317 is a fluorenyl group substituted with an ethyl group or a phenyl group.

[0340] According to an embodiment of the present specification, the above R315 and R316 are the same as or different from each other, and each is independently hydrogen, deuterium, or a substituted or unsubstituted carbazolyl group.

[0341] According to an embodiment of the present specification, the above R315 and R316 are the same as or different from each other, and each is independently hydrogen, deuterium, a carbazolyl group substituted or unsubstituted with a phenyl group or a biphenyl group.

[0342] According to an embodiment of the present specification, the above-described chemical formula HT-2 is represented by the following compound.

[0343]

[0344] According to an embodiment of the present specification, the above-described hole transport layer can include the compound of the above-described chemical formula HT-1 and / or the compound of the above-described chemical formula HT-2.

[0345] According to an embodiment of the present specification, the above-described hole transport layer can be composed of a first hole transport layer and a second hole transport layer.

[0346] According to an embodiment of the present specification, the above-described first hole transport layer can include the compound of the above-described chemical formula HT-1.

[0347] According to an embodiment of the present specification, the above-described second hole transport layer can include the compound of the above-described chemical formula HT-2.

[0348] An electron blocking layer can be provided between the hole transport layer and the light emitting layer. The above-described electron blocking layer can use the above-described spiro compound or a material known in the technical field.

[0349] The above-described light emitting layer can emit red, green, or blue light, and can be formed of a phosphorescent substance or a fluorescent substance. The above-described light emitting substance is a substance capable of receiving a hole and an electron from the hole transport layer and the electron transport layer, respectively, and emitting light in the visible light region by combining them, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. As specific examples, there are 8-hydroxy-quinoline aluminum complex (Alq3); a carbazole-based compound; a dimerized styryl compound; BAlq; 10-hydroxybenzoquinoline-metal compound; benzofuran, benzothiophene, and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymer; spiro compound; polyfluorene, rubrene, and the like, but is not limited thereto. The above-described light emitting layer can emit red, green, or blue light, and can be formed of a phosphorescent substance or a fluorescent substance. The above-described light emitting substance is a substance capable of receiving a hole and an electron from the hole transport layer and the electron transport layer, respectively, and emitting light in the visible light region by combining them, and is preferably a substance having high quantum efficiency for fluorescence or phosphorescence. As specific examples, there are 8-hydroxy-quinoline aluminum complex (Alq3); a carbazole-based compound; a dimerized styryl compound; BAlq; 10-hydroxybenzoquinoline-metal compound; benzofuran, benzothiophene, and benzimidazole-based compounds; poly(p-phenylenevinylene) (PPV)-based polymer; spiro compound; polyfluorene, rubrene, and the like, but is not limited thereto.

[0350] As a host material of the light emitting layer, there are an aromatic condensed ring derivative or a heterocycle-containing compound, etc. Specifically, as the aromatic condensed ring derivative, there are anthracene derivative, pyrene derivative, naphthalene derivative, pentacene derivative, phenanthrene compound, fluoranthene compound, etc., and as the heterocycle-containing compound, there are carbazole derivative, diphenylfuran derivative, ladder-type furan compound, pyrimidine derivative, etc., but is not limited thereto.

[0351] According to an embodiment of the present specification, the above-described host includes the compound of the following chemical formula H-1, but is not limited thereto.

[0352] [Chemical Formula H-1] ​

[0353]

[0354] In the above formula H-1,

[0355] L20and L21are the same as or different from each other, and each independently a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted 2-valent heterocyclic group,

[0356] Ar20and Ar21are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group,

[0357] R201is 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,

[0358] r201is an integer of 1 to 8, and when the above r201is 2 or more, 2 or more R201are the same as or different from each other.

[0359] In one embodiment of the present specification, the above L20and L21are the same as or different from each other, and each independently a direct bond, a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms, or a monocyclic or polycyclic 2-valent heterocyclic group having 2 to 30 carbon atoms.

[0360] In one embodiment of the present specification, the above L20and L21are the same as or different from each other, and each independently a direct bond, a phenylene group substituted or unsubstituted with deuterium, a biphenylene group substituted or unsubstituted with deuterium, a naphthylene group substituted or unsubstituted with deuterium, a 2-valent dibenzofuranyl group, or a 2-valent dibenzothiophenyl group.

[0361] In one embodiment of the present specification, the above Ar20is a substituted or unsubstituted heterocyclic group, and the above Ar21is a substituted or unsubstituted aryl group.

[0362] In one embodiment of the present specification, the above Ar20and Ar21are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0363] In one embodiment of the present specification, the above Ar20and Ar21are the same as or different from each other, and each independently 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.

[0364] In one embodiment of the present specification, the above Ar20and Ar21are the same as or different from each other, and each independently a phenyl group substituted or unsubstituted with deuterium, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group substituted or unsubstituted with deuterium, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a thienyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a naphthobenzothiophenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0365] In one embodiment of the present specification, the above Ar20and Ar21are the same as or different from each other, and each independently a phenyl group substituted or unsubstituted with deuterium, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group substituted or unsubstituted with deuterium, or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a thienyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuranyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; or a naphthobenzothiophenyl group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0366] In one embodiment of the present specification, the above Ar20and Ar21are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a 1-naphthyl group, or a 2-naphthyl group.

[0367] According to one embodiment of the present specification, the above R201is hydrogen, a biphenyl group, or a phenyl group.

[0368] According to one embodiment of the present specification, the above Chemical Formula H-1 can include the following compounds.

[0369]

[0370] When the light-emitting layer emits red light, as the light-emitting dopant, phosphorescent substances such as PIQIr(acac) (bis(1-phenylisoquinoline)acetylacetonate iridium), PQIr(acac) (bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline) iridium), PtOEP (octaethylporphyrin platinum), and the like; or fluorescent substances such as Alq3 (tris(8-hydroxyquinolino) aluminum), and the like, but not limited thereto, can be used. When the light-emitting layer emits green light, as the light-emitting dopant, phosphorescent substances such as Ir(ppy)3 (fac tris(2-phenylpyridine) iridium), and the like; or fluorescent substances such as Alq3 (tris(8-hydroxyquinolino) aluminum), and the like, but not limited thereto, can be used. When the light-emitting layer emits blue light, as the light-emitting dopant, phosphorescent substances such as (4,6-F2ppy)2Irpic, and the like; or fluorescent substances such as spiro-DPVBi, spiro-6P, DSB (diphenylstyrylbenzene), DSA (diphenylstyrylarylene), PFO-based polymers, PPV-based polymers, and the like, but not limited thereto, can be used.

[0371] In one embodiment of the present specification, the above-described dopant contains a compound of the following formula D-1.

[0372] [Chemical Formula D-1]

[0373]

[0374] In the above-described formula D-1,

[0375] R101 to R104 are the same as or different from each other, and are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or a substituted or unsubstituted silyl group,

[0376] L401 and L402 are the same as or different from each other, and are each independently a direct bond, or a substituted or unsubstituted arylene group,

[0377] R401 to R404 are the same as or different from each other, and each is independently 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,

[0378] r1 to r4 are integers of 0 to 2,

[0379] r1 to r4 are integers of 0 to 2,

[0380] In one embodiment of the present specification, R101 to R104 are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted silyl group.

[0381] In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted silyl group.

[0382] In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted silyl group.

[0383] In one embodiment of the present specification, R101 and R102 are the same as or different from each other, and each is independently hydrogen, deuterium, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted silyl group.

[0384] In one embodiment of the present specification, R103 and R104 are the same as or different from each other, and each is independently hydrogen or deuterium.

[0385] In one embodiment of the present specification, each of the above L401 and L402 is a direct bond.

[0386] In one embodiment of the present specification, the above R401 to R404 are the same as or different from each other, and each is independently a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group.

[0387] In one embodiment of the present specification, the above R401 to R404 are the same as or different from each other, and each is independently a substituted or unsubstituted monocyclic aryl group, or a substituted or unsubstituted polycyclic aryl group; or a substituted or unsubstituted heterocyclic group.

[0388] In one embodiment of the present specification, the above R401 to R404 are the same as or different from each other, and each is independently a substituted or unsubstituted phenyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted anthryl, a substituted or unsubstituted phenanthryl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted pyrenyl, or a substituted or unsubstituted fluorenyl, a substituted or unsubstituted dibenzofuranyl, or a substituted or unsubstituted dibenzothiophenyl.

[0389] In one embodiment of the present specification, the above R401 to R404 are the same as or different from each other, and each is independently a substituted or unsubstituted phenyl, or a substituted or unsubstituted dibenzofuranyl.

[0390] In one embodiment of the present specification, the above R401 to R404 are the same as or different from each other, and each is independently a substituted or unsubstituted phenyl, or a substituted or unsubstituted dibenzofuranyl.

[0391] In one embodiment of the present specification, the above R401 to R404 are the same as or different from each other, and each is independently a substituted or unsubstituted phenyl, or a substituted or unsubstituted dibenzofuranyl.

[0392] In one embodiment of the present specification, the above chemical formula D-1 is represented by the following compound.

[0393]

[0394] An electron transport layer and a light emitting layer can be provided with a hole blocking layer, and a material known in the technical field can be used.

[0395] The above electron transport layer can function to smoothly transport electrons. The electron transport substance is a substance that can receive electrons from a cathode and transfer them to a light emitting layer, and a substance having a large mobility of electrons is suitable. As specific examples, there are an Al complex of 8-hydroxyquinoline, a complex containing Alq3, an organic radical compound, a hydroxyflavone-metal complex, and the like, but are not limited thereto. The thickness of the electron transport layer can be 1 to 50 nm. When the thickness of the electron transport layer is 1 nm or more, it has an advantage that the electron transport characteristics can be prevented from being lowered, and when it is 50 nm or less, it has an advantage that the driving voltage can be prevented from rising in order to improve the electron mobility when the thickness of the electron transport layer is too thick.

[0396] The above-described electron injection layer can function to smoothly inject electrons. As the electron injection material, a compound having an electron-transporting ability, an effect of injecting electrons from the cathode, an excellent electron-injection effect to the light-emitting layer or light-emitting material, a function of preventing excitons generated in the light-emitting layer from migrating to the hole-injection layer, and an excellent thin film-forming ability is preferred, but is not limited thereto. Specifically, fluorenone, anthraquinone dimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthrone, and derivatives thereof, metal complex compounds, and nitrogen-containing five-membered ring derivatives, but is not limited thereto.

[0397] The above-described electron injection and transport layer can be manufactured using the above-described compound of Chemical Formula 1.

[0398] The above-described electron injection and transport layer can be manufactured using the above-described compound of Chemical Formula 1.

[0399] The above-described electron injection and transport layer can be manufactured using the above-described compound of Chemical Formula 1 and a metal complex together.

[0400] The above-described electron injection and transport layer can include the above-described compound of Chemical Formula 1 and a metal complex in a weight ratio of 1:10 to 10:1.

[0401] The above-described electron injection and transport layer can include the above-described compound of Chemical Formula 1 and a metal complex in a weight ratio of 1:3 to 3:1.

[0402] As the above-described metal complex compound, there are lithium 8-hydroxyquinolate, zinc bis(8-hydroxyquinolate), copper bis(8-hydroxyquinolate), manganese bis(8-hydroxyquinolate), aluminum tris(8-hydroxyquinolate), aluminum tris(2-methyl-8-hydroxyquinolate), gallium tris(8-hydroxyquinolate), beryllium bis(10-hydroxybenzo[h]quinolate), zinc bis(10-hydroxybenzo[h]quinolate), gallium bis(2-methyl-8-quinolinate) chloride, gallium bis(2-methyl-8-quinolinate)(o-cresol), aluminum bis(2-methyl-8-quinolinate)(1-naphthol), gallium bis(2-methyl-8-quinolinate)(2-naphthol), etc., but is not limited thereto.

[0403] The above-described hole-blocking layer is a layer that prevents holes from reaching the cathode, and can be formed using the same conditions as the hole-injection layer. Specifically, there are oxadiazole derivatives or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc., but is not limited thereto.

[0404] The organic light-emitting device according to the present application can be a top emission type, a bottom emission type, or a bidirectional emission type, depending on the material used.​​​

[0405] The organic light-emitting device of the present invention utilizes the above-mentioned compound to form one or more organic layers. Otherwise, it can be manufactured using conventional organic light-emitting device manufacturing methods and materials.

[0406] [Manufacturing Example]

[0407] Manufacturing Example 1-1: Manufacturing of Compound E1

[0408]

[0409] Under a nitrogen atmosphere, E1-A (20 g, 35 mmol) and E1-B (15.2 g, 35 mmol) were added to 400 ml of 1,4-dioxanone. The mixture was stirred and refluxed in 1,4-Dioxane. Potassium phosphate (22.3 g, 105.1 mmol) was then dissolved in 22 mL of water and added to the solution. After thorough stirring, palladium dibenzylacetone (0.6 g, 1.1 mmol) and tricyclohexylphosphine (0.6 g, 2.1 mmol) were added. After reacting for 5 hours, the mixture was cooled to room temperature, and the resulting solid was filtered. The solid was dissolved in 887 mL of chloroform, washed twice with water, and the organic layer was separated. Anhydrous magnesium sulfate was added, the mixture was 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 (4.4 g, 15%, MS: [M+H]). + =844).

[0410] Manufacturing Example 1-2: Manufacturing of Compound E2

[0411]

[0412] The above-described compound E2 was manufactured using the starting materials as shown in the reaction formula above, except that the same method as that used in Manufacturing Example 1-1 above was employed.

[0413] MS:[M+H] + =846

[0414] Manufacturing Examples 1-3: Manufacturing of Compound E3

[0415]

[0416] The above-described compound E3 was manufactured using the starting materials as shown in the reaction formula above, except that the same method as that used in Manufacturing Example 1-1 above was employed.

[0417] MS:[M+H] + =768

[0418] Production Example 1-4: Production of Compound E4

[0419]

[0420] The above compound E4 was produced by the same method as the production method of the above Production Example 1-1, using each starting material as shown in the above reaction formula, except for this.

[0421] MS: [M+H] + = 843

[0422] Production Example 1-5: Production of Compound E5

[0423]

[0424] The above compound E5 was produced by the same method as the production method of the above Production Example 1-1, using each starting material as shown in the above reaction formula, except for this.

[0425] MS: [M+H] + = 817

[0426] Production Example 1-6: Production of Compound E6

[0427]

[0428] The above compound E6 was produced by the same method as the production method of the above Production Example 1-1, using each starting material as shown in the above reaction formula, except for this.

[0429] MS: [M+H] + = 844

[0430] Production Example 1-7: Production of Compound E7

[0431]

[0432] The above compound E7 was produced by the same method as the production method of the above Production Example 1-1, using each starting material as shown in the above reaction formula, except for this.

[0433] MS: [M+H] + = 768

[0434] Production Example 1-8: Production of Compound E8

[0435]

[0436] The above compound E8 was produced by the same method as the production method of the above Production Example 1-1, using each starting material as shown in the above reaction formula, except for this.

[0437] MS: [M+H] + = 895

[0438] Production Example 1-9: Production of Compound E9

[0439]

[0440] The above compound E9 was produced by the same method as the production method of the above Production Example 1-1, using each starting material as shown in the above reaction formula, except for this.

[0441] MS: [M+H] + = 768

[0442] Production Example 1-10: Production of Compound E10

[0443]

[0444] The above compound E10 was produced by the same method as the production method of the above Production Example 1-1, using each starting material as shown in the above reaction formula, except for this.

[0445] MS: [M+H] + = 843

[0446] Production Example 1-11: Production of Compound E11

[0447]

[0448] The above compound E11 was produced by the same method as the production method of the above Production Example 1-1, using each starting material as shown in the above reaction formula, except for this.

[0449] MS: [M+H] + = 983

[0450] Production Example 1-12: Production of Compound E12

[0451]

[0452] The above compound E12 was produced by the same method as the production method of the above Production Example 1-1, using each starting material as shown in the above reaction formula, except for this.

[0453] MS: [M+H] + = 901

[0454] Production Example 1-13: Production of Compound E13

[0455]

[0456] The above-described compound E13 was manufactured using the starting materials as shown in the reaction formula above, except that the same method as that used in Manufacturing Example 1-1 above was employed.

[0457] MS:[M+H] + =852

[0458] Manufacturing Examples 1-14: Manufacturing of Compound E14

[0459]

[0460] The above-described compound E14 was manufactured using the starting materials as shown in the reaction formula above, except that the same method as that used in Manufacturing Example 1-1 above was employed.

[0461] MS:[M+H] + =773

[0462] [Example]

[0463] Example 1-1

[0464] ITO (Indium Tin Oxide) A glass substrate coated with a thin film of ITO was immersed in distilled water containing detergent and washed using ultrasound. The detergent used was from Fischer Co., and the distilled water was filtered twice using a filter manufactured by Millipore Co. After washing the ITO for 30 minutes, the process was repeated twice with distilled water for 10 minutes of ultrasonic washing. Following the distilled water washing, the substrate was ultrasonically washed with a solvent of isopropanol, acetone, and methanol, dried, and then transferred to a plasma cleaner. Additionally, the substrate was cleaned with oxygen plasma for 5 minutes before being transferred to a vacuum evaporation machine.

[0465] On the ITO transparent electrode prepared in this way, the following compound HI-A is applied... A hole injection layer is formed by thermal vacuum evaporation to a thickness of [amount missing]. On the aforementioned hole injection layer, [further details missing] are then vacuum evaporated sequentially.

[0466] The following compounds HAT and The following compound HT-A is used to form the first hole transport layer and the second hole transport layer.

[0467] Next, on the aforementioned second hole transport layer, with a film thickness... A light-emitting layer was formed by vacuum evaporation of the following compounds BH and BD at a weight ratio of 25:1.

[0468] On the above light emitting layer, the compound El produced in the above and the following compound LiQ were vacuum-evaporated at a weight ratio of 1:1, thereby forming an electron injecting and transporting layer with a thickness of On the above electron injecting and transporting layer, lithium fluoride (LiF) was evaporated with a thickness of and aluminum was evaporated with a thickness of to form a cathode.

[0469]

[0470] In the above process, the evaporation speed of the organic matter was maintained at to The evaporation speed of the lithium fluoride of the cathode was maintained at and the evaporation speed of the aluminum was maintained at In the evaporation, the vacuum degree was maintained at 1 x 10 -7 to 5 x 10 -5 torr, thereby producing an organic light emitting device.

[0471] Example 1-2 to Example 1-14

[0472] Instead of the compound El of the above Example 1-1, the following compounds E2 to E14 described in Table 1 were respectively used, and otherwise, an organic light emitting device was produced by the same method as the above Example 1-1.

[0473] Comparative Example 1-1 to Comparative Example 1-4

[0474] Instead of the compound El of the above Example 1-1, the following compounds ET-1 to ET-4 described in Table 1 were respectively used, and otherwise, an organic light emitting device was produced by the same method as the above Example 1-1. The structures of the compounds ET-1 to ET-4 of the following Table 1 are shown below.

[0475]

[0476] [Experimental Example]

[0477] The organic light emitting devices produced in the above Examples 1-1 to 1-14 and Comparative Examples 1-1 to 1-4 were measured for driving voltage and luminous efficiency at a current density of 10 mA / cm 2 and for time (T90) at which the initial brightness became 90% at a current density of 20 mA / cm 2 The results are shown in the following Table 1.

[0478] [Table 1]

[0479]

[0480] As shown in the above Table 1, the organic light emitting devices of Examples 1-1 to 1-14 according to the present specification using the compounds represented by Chemical Formula 1 for the electron injection and electron transport layers of the organic light emitting devices showed excellent characteristics in terms of low driving voltage, efficiency, and lifespan.

[0481] Compounds ET-1 and ET-4 are cases where aryl groups are not substituted with a cyano group. Such compounds are difficult to adjust electron migration due to a decrease in dipole moment, and thus Comparative Example 1-1 and Comparative Example 1-4 using the compounds ET-1 and ET-4 showed high driving voltage, low efficiency, and low lifespan characteristics compared to Examples 1-1 to 1-14 using the compounds of Chemical Formula 1 according to the present specification.

[0482] Compounds ET-2 and ET-3 are cases where heteroaryl groups are respectively bound to the meta- and meta-positions of the biphenyl group, unlike the present application where heteroaryl groups are respectively bound to the para- and meta-positions of the biphenyl group.

[0483] Such compounds decrease electron mobility due to an increase in energy barrier with the light emitting layer, and thus Comparative Example 1-2 and Comparative Example 1-3 using the compounds ET-2 and ET-3 showed high driving voltage, low efficiency, and / or low lifespan characteristics compared to Examples 1-1 to 1-14 using the compounds of Chemical Formula 1 according to the present specification.

Claims

1. A compound of the following chemical formula 1: [Chemical Formula 1] [Chemical Formula 2] In the chemical formula 1, X1 to X3 may be the same or different from each other, each being independently N or CR, and more than two of X1 to X3 are N. The 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 may be the same as or different from each other, and each is independently an aryl group with 6 to 60 substituted or unsubstituted carbon atoms, or a heteroaryl group with 2 to 60 substituted or unsubstituted carbon atoms. Ar3 is the chemical formula 2, which is substituted with one or more cyano groups and can optionally be further substituted with deuterium. R1 and R2 may be the same as or different from each other, and each is independently hydrogen, deuterium, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. HAr is a triazine group substituted or unsubstituted with two substituents selected independently from deuterium, aryl groups with 6 to 60 carbon atoms, and heteroaryl groups with 2 to 60 carbon atoms; a pyrimidinyl group substituted or unsubstituted with one to three substituents selected independently from deuterium, alkyl groups with 1 to 60 carbon atoms, aryl groups with 6 to 60 carbon atoms, and heteroaryl groups with 2 to 60 carbon atoms; or a pyrimidinyl group substituted or unsubstituted with deuterium, substituted or unsubstituted carbon atoms. The following are considered quinazolinyl groups: aryl groups, and heteroaryl groups having 2 to 60 carbon atoms, substituted or unsubstituted; benzothiophene-pyrimidinyl groups, substituted or unsubstituted; or benzofuran-pyrimidinyl groups, substituted or unsubstituted. n is an integer from 1 to 4. m is an integer from 1 to 3. When n is 2 or more, R1 is either the same or different from each other. When m is 2 or more, R² is either the same or different from each other. In the chemical formula 2, * indicates the site where it combines with chemical formula 1. a is 0 or 1. b is 0 or 1.

2. The compound according to claim 1, wherein, The chemical formula 1 is any one of the following chemical formulas 1-1 to 1-5: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formulas 1-3] [Chemical Formulas 1-4] [Chemical Formulas 1-5] In the chemical formulas 1-1 to 1-5, X1 to X3, Ar1 to Ar3, n, and m are defined as in the chemical formula 1. R1 and R2 may be the same as or different from each other, and each can be hydrogen or deuterium independently. R3 and R4 may be the same as or different from each other, and each is independently deuterium, an aryl group with 6 to 60 substituted or unsubstituted carbon atoms, or a heteroaryl group with 2 to 60 substituted or unsubstituted carbon atoms. R5 is hydrogen, 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 deuterium, an aryl group with 6 to 60 substituted or unsubstituted carbon atoms, or a heteroaryl group with 2 to 60 substituted or unsubstituted carbon atoms. o is an integer from 1 to 3. When o is 2 or more, R5 can be the same or different from each other.

3. The compound according to claim 1, wherein, The HAr is a triazine group substituted with two substituents selected independently from deuterium, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; a pyrimidinyl group substituted with one to three substituents selected independently from deuterium, substituted or unsubstituted alkyl groups having 1 to 60 carbon atoms, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms, and substituted or unsubstituted heteroaryl groups having 2 to 60 carbon atoms; or a pyrimidinyl group substituted with deuterium, substituted or unsubstituted aryl groups having 6 to 60 carbon atoms. A quinazolinyl group substituted with one of the following: an aryl group of 60 to 60 carbon atoms, or a heteroaryl group of 2 to 60 carbon atoms, substituted or unsubstituted; a benzothiophene-pyrimidinyl group substituted with one of the following: a deuterium group, an aryl group of 6 to 60 carbon atoms, or a heteroaryl group of 2 to 60 carbon atoms, substituted or unsubstituted; or a benzofuran-pyrimidinyl group substituted with one of the following: a deuterium group, an aryl group of 6 to 60 carbon atoms, or a heteroaryl group of 2 to 60 carbon atoms, substituted or unsubstituted.

4. The compound according to claim 1, wherein, The Ar1 and Ar2 may be the same as or different from each other, and each may be independently substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidinyl, or substituted or unsubstituted quinazolinyl.

5. The compound according to claim 1, wherein, X1 to X3 are all N.

6. The compound according to claim 2, wherein, R3 and R4 may be the same as or different from each other, and each is independently deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridyl.

7. The compound according to claim 2, wherein, The R5 is hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridyl.

8. The compound according to claim 2, wherein, The R6 is deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted naphthyl, or substituted or unsubstituted pyridyl.

9. The compound according to claim 1, wherein, Chemical formula 1 is any of the following structural formulas:

10. An organic light-emitting device, wherein, include: First electrode; Second electrode; And an organic layer of one or more layers disposed between the first electrode and the second electrode, wherein one or more of the organic layers comprises the compound of any one of claims 1 to 9.

11. The organic light-emitting device according to claim 10, wherein, The organic layer includes one or more of an electron transport layer, an electron injection layer, and an electron injection and transport layer, wherein one or more of the layers contains the compound.

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