Compound and organic light-emitting element comprising same

Abstract

The present specification relates to chemical formula 1 and an organic light-emitting element comprising same. The organic light-emitting element comprises: a first electrode; a second electrode; and one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers among the organic material layers may comprise a compound of chemical formula 1. Specifically, the organic material layers include one or more layers of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and one or more layers among the layers may include the compound of chemical formula 1.

Description

Compound and organic light-emitting device containing the same

[0001] This application claims the benefit of Korean Patent Application No. 10-2024-0002816, filed with the Korean Intellectual Property Office on January 8, 2024, the entire contents of which are incorporated herein by reference.

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

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

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

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

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

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

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

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

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

[0013] R1 to R5 are the same as or different from each other, and each independently represent hydrogen; deuterium; a nitrile group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0014] Ar1 is a substituted or unsubstituted heteroarylene group having 6 to 20 carbon atoms containing 2 or more N,

[0015] Ar2 is hydrogen; deuterium; a nitrile group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0016] A is the following chemical formula 2-1 or chemical formula 2-2,

[0017] [Chemical Formula 2-1] [Chemical Formula 2-2]

[0018]

[0019] In the above chemical formula 2-1 or chemical formula 2-2,

[0020] * is a portion that is bonded to the above chemical formula 1,

[0021] One or two of X1 to X7 are N, and the rest are CR',

[0022] R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group,

[0023] a and c are integers from 1 to 4, respectively,

[0024] b is an integer from 1 to 3,

[0025] d and e are each integers from 1 to 5,

[0026] When a is 2 or more, R1 are equal or different,

[0027] When b is 2 or more, R2 are equal or different,

[0028] When c is 2 or more, R3 are equal or different,

[0029] When d is 2 or more, R4 are equal or different,

[0030] When e is 2 or greater, R5 are equal or different.

[0031] In addition, according to one embodiment of the present invention, an organic light-emitting device is provided, including a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers includes the above-described compound.

[0032] The compound of the present invention can be used as a material for an organic layer of an organic light-emitting device. When an organic light-emitting device is manufactured by including the compound of the present invention, an organic light-emitting device having high efficiency, low voltage, and long life characteristics can be obtained. In addition, when the compound of the present invention is included in an electron injection and transport layer of an organic light-emitting device, the intramolecular polarization is high, thereby enhancing the effect of electron transfer, and thus an organic light-emitting device having long life characteristics can be manufactured.

[0033] Instead of narrowing the distance between electron transport groups, the compound of the present invention maximizes electron mobility by limiting the substitution position of the linking group in the ortho direction to appropriately break conjugation within the molecule, thereby exhibiting high efficiency characteristics.

[0034] Long-life characteristics were also maintained by adding quinoline or quinazoline, which are highly electronegative substituents.

[0035] Figures 1 and 2 illustrate examples of organic light-emitting devices according to the present invention.

[0036] <Explanation of symbols>

[0037] 1: Substrate

[0038] 2: Bipolar

[0039] 3: Organic layer

[0040] 4: Cathode

[0041] 5: Hole injection layer

[0042] 6: Hole transport layer

[0043] 7: Electron blocking layer

[0044] 8: Emissive layer

[0045] 9: The hole-blocking layer

[0046] 10: Electron injection and transport layer

[0047] The following describes this specification in more detail.

[0048] In this specification, when a part is said to "include" a certain component, this does not mean that it excludes other components, but rather that it may include other components, unless otherwise specifically stated.

[0049] In this specification, when it is said that a member is located “on” another member, this includes not only cases where the member is in contact with the other member, but also cases where another member exists between the two members.

[0050] Examples of substituents in this specification are described below, but are not limited thereto.

[0051] The term "substitution" above means that a hydrogen atom bonded to a carbon atom of a compound is replaced with another substituent, and the position of substitution is not limited as long as it is a position where the hydrogen atom is replaced, i.e., a position where the substituent can be replaced, and when two or more are substituted, the two or more substituents may be the same or different from each other.

[0052] The term "substituted or unsubstituted" as used herein means substituted with one or more substituents selected from the group consisting of deuterium; a halogen group; a cyano group (-CN); a silyl group; a boron group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; and a substituted or unsubstituted heterocyclic group, or substituted with a substituent in which two or more substituents among the above-mentioned substituents are connected, or has no substituents. For example, "a substituent connected with two or more substituents" may be a biphenyl group. That is, the biphenyl group may be an aryl group, or may be interpreted as a substituent in which two phenyl groups are connected.

[0053] Examples of the above substituents are described below, but are not limited thereto.

[0054] In this specification, examples of halogen groups include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0055] In the present specification, a silyl group may be substituted or unsubstituted with deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of the silyl group include, but are not limited to, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group, and a phenylsilyl group.

[0056] In the present specification, a boron group may be substituted or unsubstituted with deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group. Specific examples of the boron group include, but are not limited to, a trimethyl boron group, a triethyl boron group, a t-butyldimethyl boron group, a triphenyl boron group, and a phenyl boron group.

[0057] In the present specification, the alkyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include, but are not limited to, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and the like.

[0058] In the present specification, the amine group may be selected from the group consisting of -NH2; an alkylamine group; an N-alkylarylamine group; an arylamine group; an N-arylheteroarylamine group; an N-alkylheteroarylamine group and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30. Specific examples of the amine group include a methylamine group; a dimethylamine group; an ethylamine group; a diethylamine group; a phenylamine group; a naphthylamine group; a biphenylamine group; anthracenylamine group; a 9-methylanthracenylamine group; a diphenylamine group; a ditolylamine group; an N-phenyltolylamine group; a triphenylamine group; an N-phenylbiphenylamine group; an N-phenylnaphthylamine group; an N-biphenylnaphthylamine group; an N-naphthylfluorenylamine group; an N-phenylphenanthrenylamine group; an N-biphenylphenanthrenylamine group; an N-phenylfluorenylamine group; N-phenylterphenylamine group; N-phenanthrenylfluorenylamine group; N-biphenylfluorenylamine group, etc., but are not limited thereto.

[0059] In this specification, an N-alkylarylamine group means an amine group in which an alkyl group and an aryl group are substituted for N of the amine group.

[0060] In this specification, an N-arylheteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted for N of the amine group.

[0061] In this specification, an N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroaryl group are substituted for N of the amine group.

[0062] In the present specification, the alkyl group among the alkylamine group, N-arylalkylamine group, alkylthioxy group, alkylsulfoxy group, and N-alkylheteroarylamine group is the same as the examples of the alkyl group described above. Specifically, the alkylthioxy group includes a methylthioxy group; an ethylthioxy group; a tert-butylthioxy group; a hexylthioxy group; an octylthioxy group, etc., and the alkylsulfoxy group includes, but is not limited to, a mesyl group; an ethylsulfoxy group; a propylsulfoxy group; a butylsulfoxy group, etc.

[0063] In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. In one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. In another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, examples thereof include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.

[0064] In the present specification, the aryl group is not particularly limited, but is preferably one having 6 to 60 carbon atoms, and may be a monocyclic aryl group, a bicyclic aryl group, or a tricyclic or more aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms. The monocyclic aryl group may be, but is not limited to, a phenyl group, a biphenyl group, a terphenyl group, or the like. The bicyclic aryl group may be, but is not limited to, a naphthyl group, a pentalene group, an indene group, an azulene group, a heptalene group, or the like. The tricyclic or more aryl group may be, but is not limited to, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenylene group, a chrysenyl group, a fluorenyl group, or the like.

[0065] In the present specification, a heteroaryl group is a ring group containing at least one of N, O, P, S, Si, and Se as a heteroatom, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heteroaryl group is 2 to 30.

[0066] In the present specification, the heteroaryl group may be a monocyclic heteroaryl group, a bicyclic heteroaryl group, or a tricyclic or higher heteroaryl group. Examples of the monocyclic heteroaryl group include, but are not limited to, a pyridine group, a pyrrole group, a pyrimidine group, a pyridazinyl group, a furan group, a thiophene group, an imidazole group, a pyrazole group, etc. Examples of the bicyclic heteroaryl group include, but are not limited to, a quinol group, an isoquinoline group, a quinazoline group, a quinoxaline group, an indole group, a benzothiophene group, a benzofuran group, etc. Examples of the tricyclic or higher heteroaryl group include, but are not limited to, a dibenzofuran group, a dibenzothiophene group, a carbazole group, etc.

[0067] In this specification, the arylene group is as defined in the above aryl group, except that it is a divalent group.

[0068] In this specification, the heteroarylene group is as defined in the heteroaryl group above, except that it is divalent.

[0069] In the present specification, a condensed ring refers to a ring in which two or more selected from an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, and a heterocycle are condensed, and the definition of the cycloalkyl group is applied to the aliphatic hydrocarbon ring except that it is not monovalent, the definition of the aromatic hydrocarbon ring is applied to the aryl group except that it is not monovalent, and the definition of the heterocycle is applied to the heteroaryl group except that it is not monovalent.

[0070] In this specification, the chemical formula 1 is any one of the following chemical formulas 1-1 to 1-10.

[0071] [Chemical Formula 1-1]

[0072]

[0073] [Chemical Formula 1-2]

[0074]

[0075] [Chemical Formula 1-3]

[0076]

[0077] [Chemical Formula 1-4]

[0078]

[0079] [Chemical Formula 1-5]

[0080]

[0081] [Chemical Formula 1-6]

[0082]

[0083] [Chemical Formula 1-7]

[0084]

[0085] [Chemical Formula 1-8]

[0086]

[0087] [Chemical Formula 1-9]

[0088]

[0089] [Chemical Formula 1-10]

[0090]

[0091] In the above chemical formulas 1-1 to 1-10, R1 to R5, Ar1, Ar2, A and a to e are as defined in the above chemical formula 1.

[0092] In one embodiment of the present invention, the chemical formula 1 is any one of the following chemical formulas 1-1-1 to 1-1-10.

[0093] [Chemical Formula 1-1-1]

[0094]

[0095] [Chemical Formula 1-1-2]

[0096]

[0097] [Chemical Formula 1-1-3]

[0098]

[0099] [Chemical Formula 1-1-4]

[0100]

[0101] [Chemical Formula 1-1-5]

[0102]

[0103] [Chemical Formula 1-1-6]

[0104]

[0105] [Chemical Formula 1-1-7]

[0106]

[0107] [Chemical Formula 1-1-8]

[0108]

[0109] [Chemical Formula 1-1-9]

[0110]

[0111] [Chemical Formula 1-1-10]

[0112]

[0113] In the above chemical formulas 1-1-1 to 1-1-10, R4, R5, Ar1, Ar2, A, d and e are as defined in the above chemical formula 1.

[0114] According to one embodiment of the present specification, R1 to R3 of the chemical formulae 1-1 to 1-10 are hydrogen or deuterium.

[0115] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms and containing 2 or more N.

[0116] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted heteroarylene group having 3 to 20 carbon atoms and containing 2 or more N.

[0117] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted heteroarylene group having 3 to 15 carbon atoms and containing 2 or more N.

[0118] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 3 to 30 carbon atoms and containing 2 or more N.

[0119] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 3 to 20 carbon atoms and containing 2 or more N.

[0120] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted monocyclic or polycyclic heteroarylene group having 3 to 15 carbon atoms and containing 2 or more N.

[0121] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted monocyclic heteroarylene group having 3 to 30 carbon atoms and containing 2 or more N.

[0122] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted monocyclic heteroarylene group having 3 to 20 carbon atoms and containing 2 or more N.

[0123] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted monocyclic heteroarylene group having 3 to 15 carbon atoms and containing 2 or more N.

[0124] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted divalent triazine group; or a substituted or unsubstituted divalent pyrimidine group.

[0125] According to one embodiment of the present specification, Ar1 is a divalent triazine group substituted or unsubstituted with hydrogen or an aryl group; or a divalent pyrimidine group substituted or unsubstituted with hydrogen or an aryl group.

[0126] According to one embodiment of the present specification, Ar1 is a divalent triazine group unsubstituted or substituted with hydrogen, a phenyl group, a biphenyl group or a naphthyl group; or a divalent pyrimidine group unsubstituted or substituted with hydrogen, a phenyl group, a biphenyl group or a naphthyl group.

[0127] According to one embodiment of the present specification, Ar1 is a divalent triazine group substituted or unsubstituted with hydrogen, a phenyl group, a biphenyl group, or a naphthyl group.

[0128] According to one embodiment of the present specification, Ar1 is a divalent pyrimidine group substituted or unsubstituted with hydrogen, a phenyl group, a biphenyl group or a naphthyl group.

[0129] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted divalent quinazoline group.

[0130] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted divalent quinoxaline group.

[0131] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted divalent imidazolyl group.

[0132] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted divalent benzoimidazolyl group.

[0133] According to one embodiment of the present specification, Ar1 is a divalent quinazoline group substituted or unsubstituted with deuterium or an aryl group.

[0134] According to one embodiment of the present specification, Ar1 is a divalent quinoxaline group substituted or unsubstituted with deuterium or an aryl group.

[0135] According to one embodiment of the present specification, Ar1 is a divalent imidazolyl group unsubstituted or substituted with deuterium, an alkyl group or an aryl group.

[0136] According to one embodiment of the present specification, Ar1 is a divalent benzimidazolyl group substituted or unsubstituted with deuterium, an alkyl group, or an aryl group.

[0137] According to one embodiment of the present specification, Ar2 is hydrogen; deuterium; a nitrile group; a halogen group; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; or a substituted or unsubstituted condensed ring group having 3 to 30 carbon atoms.

[0138] According to one embodiment of the present specification, Ar2 is hydrogen; deuterium; a nitrile group; a halogen group; 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.

[0139] According to one embodiment of the present specification, Ar2 is hydrogen; deuterium; a nitrile group; a halogen group; a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0140] According to one embodiment of the present specification, Ar2 is hydrogen; deuterium; a nitrile group; a halogen group; a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

[0141] According to one embodiment of the present specification, Ar2 is hydrogen; deuterium; a nitrile group; a halogen group; an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or two or more linked groups; or an aryl group having 6 to 30 carbon atoms substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group.

[0142] According to one embodiment of the present specification, Ar2 is hydrogen; deuterium; a nitrile group; a halogen group; an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or two or more linked groups; or an aryl group having 6 to 20 carbon atoms substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group.

[0143] According to one embodiment of the present specification, Ar2 is hydrogen; deuterium; a nitrile group; a halogen group; an alkyl group having 1 to 6 carbon atoms substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group, or two or more linked groups; or an aryl group having 6 to 15 carbon atoms substituted or unsubstituted with one or more groups selected from the group consisting of deuterium, a halogen group, an alkyl group, an aryl group, and a heterocyclic group.

[0144] According to one embodiment of the present specification, Ar2 is hydrogen; deuterium; a nitrile group; a halogen group; a methyl group; an ethyl group; a terbutyl group; an isopropyl group; a phenyl group; a biphenyl group; a naphthyl group; an anthracene group; or a phenanthrene group.

[0145] According to one embodiment of the present specification, Ar2 is hydrogen; deuterium; a nitrile group; a halogen group; a methyl group; an ethyl group; a phenyl group; a biphenyl group; or a naphthyl group.

[0146] According to one embodiment of the present specification, Ar2 is hydrogen; deuterium; a phenyl group; a biphenyl group; or a naphthyl group.

[0147] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently represent hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group.

[0148] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently represent hydrogen, deuterium, a nitrile group, a halogen group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0149] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently represent hydrogen, deuterium, a nitrile group, a halogen group, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0150] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently represent hydrogen, deuterium, a nitrile group, a halogen group, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.

[0151] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently represent hydrogen, deuterium, a nitrile group, a halogen group, or an alkyl group having 1 to 10 carbon atoms.

[0152] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently represent hydrogen, deuterium, a nitrile group, F, Cl, Br, I, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a terbutyl group, a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, a pyrrole group, a furan group, a thiophene group, a triazine group, a pyrimidine group, a pyridine group, a carbazole group, a dibenzofuran group, or a dibenzothiophene group.

[0153] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, F, Cl, Br, I, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a phenyl group, a naphthyl group, or a terbutyl group.

[0154] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a nitrile group, a halogen group, a phenyl group, or a naphthyl group.

[0155] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and are each independently hydrogen, deuterium, a phenyl group, or a naphthyl group.

[0156] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and are each independently hydrogen or deuterium.

[0157] According to one embodiment of the present specification, R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0158] According to one embodiment of the present specification, R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0159] According to one embodiment of the present specification, R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0160] According to one embodiment of the present specification, R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0161] According to one embodiment of the present specification, R' is hydrogen; deuterium; or a substituted or unsubstituted ethyl group or a substituted or unsubstituted methyl group.

[0162] According to one embodiment of the present specification, one or two of X1 to X7 are N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0163] According to one embodiment of the present specification, one of X1 to X7 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0164] According to one embodiment of the present specification, any two of X1 to X7 are N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0165] According to one embodiment of the present specification, one of X1 to X7 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0166] According to one embodiment of the present specification, one of X1 to X7 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0167] According to one embodiment of the present specification, one of X1 to X7 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0168] According to one embodiment of the present specification, one of X1 to X7 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms.

[0169] According to one embodiment of the present specification, one of X1 to X7 is N, the others are CR', and R' is hydrogen; deuterium; or a methyl group.

[0170] According to one embodiment of the present specification, any two of X1 to X7 are N, the rest are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0171] According to one embodiment of the present specification, any two of X1 to X7 are N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0172] According to one embodiment of the present specification, any two of X1 to X7 are N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0173] According to one embodiment of the present specification, any two of X1 to X7 are N, the rest are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms.

[0174] According to one embodiment of the present specification, any two of X1 to X7 are N, the others are CR', and R' is hydrogen; deuterium; or a methyl group.

[0175] According to one embodiment of the present specification, one of X1 to X3 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0176] According to one embodiment of the present specification, any two of X1 to X3 are N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0177] According to one embodiment of the present specification, one of X1 to X3 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0178] According to one embodiment of the present specification, one of X1 to X3 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0179] According to one embodiment of the present specification, one of X1 to X3 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0180] According to one embodiment of the present specification, one of X1 to X3 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms.

[0181] According to one embodiment of the present specification, one of X1 to X3 is N, the other is CR', and R' is hydrogen; deuterium; or a methyl group.

[0182] According to one embodiment of the present specification, any two of X1 to X3 are N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0183] According to one embodiment of the present specification, any two of X1 to X3 are N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0184] According to one embodiment of the present specification, any two of X1 to X3 are N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0185] According to one embodiment of the present specification, any two of X1 to X3 are N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms.

[0186] According to one embodiment of the present specification, any two of X1 to X3 are N, the others are CR', and R' is hydrogen; deuterium; or a methyl group.

[0187] According to one embodiment of the present specification, one of X4 to X7 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0188] According to one embodiment of the present specification, any two of X4 to X7 are N, the remainder are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0189] According to one embodiment of the present specification, one of X4 to X7 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0190] According to one embodiment of the present specification, one of X4 to X7 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0191] According to one embodiment of the present specification, one of X4 to X7 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0192] According to one embodiment of the present specification, one of X4 to X7 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms.

[0193] According to one embodiment of the present specification, one of X4 to X7 is N, the others are CR', and R' is hydrogen; deuterium; or a methyl group.

[0194] According to one embodiment of the present specification, any two of X4 to X7 are N, the rest are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0195] According to one embodiment of the present specification, any two of X4 to X7 are N, the rest are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0196] According to one embodiment of the present specification, any two of X4 to X7 are N, the rest are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0197] According to one embodiment of the present specification, any two of X4 to X7 are N, the rest are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms.

[0198] According to one embodiment of the present specification, any two of X4 to X7 are N, the others are CR', and R' is hydrogen; deuterium; or a methyl group.

[0199] According to one embodiment of the present specification, the chemical formula 1 is one of the following structural formulas.

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235]

[0236] According to one embodiment of the present specification, R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0237] According to one embodiment of the present specification, R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0238] According to one embodiment of the present specification, R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0239] According to one embodiment of the present specification, R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0240] According to one embodiment of the present specification, R' is hydrogen; deuterium; or a substituted or unsubstituted ethyl group or methyl group.

[0241] The substituent of the compound of the above chemical formula 1 can be combined by a method known in the art, and the type, position or number of the substituent can be changed according to a technique known in the art.

[0242] In addition, by introducing various substituents into the core structure as described above, compounds having the unique properties of the introduced substituents can be synthesized. For example, by introducing substituents mainly used in hole injection layer materials, hole transport materials, light-emitting layer materials, and electron transport layer materials used in the manufacture of organic light-emitting devices into the core structure, a material satisfying the conditions required for each organic layer can be synthesized.

[0243] In addition, an organic light-emitting device according to the present invention is an organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises the above-described compound.

[0244] The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.

[0245] The above compound can be formed into an organic layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light-emitting device. Here, the solution coating method refers to, but is not limited to, spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, etc.

[0246] The organic layer of the organic light-emitting device of the present invention may be formed as a single layer structure, but may also be formed as a multilayer structure in which two or more organic layers are laminated. For example, the organic light-emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a layer that simultaneously injects holes and transports holes, a light-emitting layer, an electron transport layer, an electron injection layer, etc. as the organic layers. However, the structure of the organic light-emitting device is not limited thereto and may include a smaller number of organic layers or a larger number of organic layers.

[0247] In the organic light-emitting device of the present invention, the organic layer may include at least one of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and at least one of the layers may include a compound represented by the chemical formula 1.

[0248] In another organic light-emitting device, the organic layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include a compound represented by the chemical formula 1.

[0249] In the organic light-emitting device of the present invention, the electron injection and transport layer includes the compound of the chemical formula 1 and a metal complex.

[0250] In the organic light-emitting device of the present invention, the organic layer may include at least one layer among a hole injection layer, a hole transport layer, and a layer that simultaneously injects holes and transports holes, and at least one layer among the layers may include a compound represented by the chemical formula 1.

[0251] In another organic light-emitting device, the organic layer may include a hole injection layer or a hole transport layer, and the hole transport layer or the hole injection layer may include a compound represented by the chemical formula 1.

[0252] In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

[0253] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0254] (1) Anode / hole transport layer / light emitting layer / cathode

[0255] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0256] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0257] (4) Anode / hole transport layer / light emitting layer / electron transport layer / cathode

[0258] (5) Anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0259] (6) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0260] (7) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0261] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0262] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0263] (10) Anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

[0264] (11) Anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0265] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

[0266] (13) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0267] (14) Anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

[0268] (15) Anode / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0269] (16) Anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

[0270] (17) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0271] (18) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron injection and transport layer / cathode

[0272] The structure of the organic light-emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.

[0273] Figure 1 illustrates the structure of an organic light-emitting device in which an anode (2), an organic layer (3), and a cathode (4) are sequentially laminated on a substrate (1). In such a structure, the compound represented by the chemical formula 1 may be included in the organic layer (3).

[0274] Figure 2 illustrates the structure of an organic light-emitting device in which an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light-emitting layer (8), a hole blocking layer (9), an electron injection and transport layer (10), and a cathode (4) are sequentially laminated on a substrate (1). The compound represented by the chemical formula 1 may be included in the hole blocking layer (9) or the electron injection and transport layer (10).

[0275] For example, the organic light-emitting device according to the present invention can be manufactured by forming an anode by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation, and then forming an organic layer including at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, a layer that simultaneously transports and injects holes, a light-emitting layer, an electron transport layer, an electron injection layer, and a layer that simultaneously transports and injects electrons, and then depositing a material that can be used as a cathode thereon. In addition to this method, an organic light-emitting device can also be manufactured by sequentially depositing a cathode material, an organic layer, and an anode material on a substrate.

[0276] The above organic layer may have a multilayer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure. In addition, the above organic layer may be manufactured with a smaller number of layers using various polymer materials by a solvent process other than a deposition method, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer.

[0277] The above anode is an electrode that injects holes, and as the anode material, a material having a high work function is generally preferred so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline.

[0278] The above cathode is an electrode that injects electrons, and the cathode material is preferably a material with a low work function to facilitate electron injection into the organic layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead, or alloys thereof; multilayered materials such as LiF / Al or LiO2 / Al.

[0279] The above hole injection layer is a layer that facilitates the injection of holes from the anode to the light-emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrine, oligothiophene, arylamine-based organic compounds, hexanitrilehexaazatriphenylene-based organic compounds, quinacridone-based organic compounds, perylene-based organic compounds, anthraquinone, and conductive polymers such as polyaniline and polythiophene. The thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage of being able to prevent the hole injection characteristics from being deteriorated, and if it is 150 nm or less, there is an advantage of being able to prevent the driving voltage from being increased to improve the movement of holes due to the thickness of the hole injection layer being too thick.

[0280] According to one embodiment of the present specification, the hole injection layer includes, but is not limited to, a compound represented by the following chemical formula HI-1.

[0281] According to one embodiment of the present specification, the hole injection layer may be a compound of the following chemical formula HI-1.

[0282] [Chemical formula HI-1]

[0283]

[0284] In the above chemical formula HI-1,

[0285] R201 to R204 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to form a substituted or unsubstituted ring,

[0286] In one embodiment of the present specification, R201 is a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or is bonded to an adjacent group to form a substituted or unsubstituted ring.

[0287] In one embodiment of the present specification, R201 to R204 are the same as or different from each other, and each independently represents hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0288] In one embodiment of the present specification, R201 to R204 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0289] In one embodiment of the present specification, R201 to R204 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0290] In one embodiment of the present specification, R202 and R204 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group.

[0291] In one embodiment of the present specification, R201 and R203 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0292] In one embodiment of the present specification, R201 and R203 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0293] In one embodiment of the present specification, R201 and R203 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group.

[0294] In one embodiment of the present specification, R202 and R204 are the same as or different from each other, and each independently represents a substituted or unsubstituted heteroaryl group.

[0295] In one embodiment of the present specification, R202 and R204 are the same as or different from each other, and each independently represent a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0296] In one embodiment of the present specification, R202 and R204 are the same as or different from each other, and each independently represent a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.

[0297] In one embodiment of the present specification, R202 and R204 are the same as or different from each other, and each independently represents a substituted or unsubstituted dibenzofuranyl group; a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

[0298] In one embodiment of the present specification, R202 and R204 are the same as or different from each other, and each independently represents a carbazolyl group substituted or unsubstituted with an aryl group.

[0299] In one embodiment of the present specification, R202 and R204 are the same as or different from each other, and each independently represents a carbazolyl group unsubstituted or substituted with a phenyl group.

[0300] In one embodiment of the present specification, the chemical formula HI-1 is represented by the following compound.

[0301]

[0302] The above-mentioned hole transport layer can play a role in facilitating hole transport. A hole transport material capable of transporting holes from the anode or hole injection layer and transferring them to the light-emitting layer, and a material with high hole mobility, is suitable. Specific examples include, but are not limited to, arylamine-based organic compounds, conductive polymers, and block copolymers with both conjugated and non-conjugated portions.

[0303] According to one embodiment of the present specification, the hole transport layer includes, but is not limited to, a compound represented by the following chemical formula HT-1.

[0304] [Chemical formula HT-1]

[0305]

[0306] In the above chemical formula HT-1,

[0307] At least one of X'1 to X'6 is N, and the rest are CH,

[0308] R309 to R314 are the same or different, and each independently represent hydrogen; deuterium; a nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, or combine with adjacent groups to form a substituted or unsubstituted ring.

[0309] According to one embodiment of the present specification, X'1 to X'6 are N.

[0310] According to one embodiment of the present specification, R309 to R314 are nitrile groups.

[0311] According to one embodiment of the present specification, the chemical formula HT-1 is represented by the following compound.

[0312]

[0313] According to one embodiment of the present specification, the hole transport layer may further include a compound of the following chemical formula HT-2.

[0314] [Chemical formula HT-2]

[0315]

[0316] In the above chemical formula HT-2,

[0317] L101 is a direct bond; or a substituted or unsubstituted arylene group,

[0318] R101 to R103 are the same or different, and each independently represents a substituted or unsubstituted aryl group.

[0319] According to one embodiment of the present specification, L101 is a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0320] According to one embodiment of the present specification, L101 is a direct bond; or a substituted or unsubstituted phenylene group.

[0321] According to one embodiment of the present specification, L101 is a direct bond; or a phenylene group.

[0322] According to one embodiment of the present specification, R101 to R103 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group.

[0323] According to one embodiment of the present specification, R101 to R103 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrenyl group; a substituted or unsubstituted triphenylenyl group; a substituted or unsubstituted pyrene group; or a substituted or unsubstituted fluorenyl group.

[0324] According to one embodiment of the present specification, R101 to R103 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; or a substituted or unsubstituted fluorenyl group.

[0325] According to one embodiment of the present specification, R101 to R103 are the same as or different from each other, and each independently represents a phenyl group; a biphenyl group; or a fluorenyl group substituted with an alkyl group.

[0326] According to one embodiment of the present specification, the chemical formula HT-2 is represented by the following compound.

[0327]

[0328] An electron blocking layer may be provided between the hole transport layer and the light emitting layer. The electron blocking layer may be formed using the aforementioned spiro compound or a material known in the art.

[0329] The above-mentioned light-emitting layer can emit red, green, or blue light, and can be made of a phosphorescent material or a fluorescent material. The above-mentioned light-emitting material is a material that can emit light in the visible light range by transporting holes and electrons from a hole transport layer and an electron transport layer, respectively, and combining them, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole series compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; benzoxazole, benzthiazole, and benzimidazole series compounds; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc.

[0330] Host materials for the light-emitting layer include condensed aromatic ring derivatives or heterocyclic compound-containing compounds. Specifically, condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc., and heterocyclic compound-containing compounds include, but are not limited to, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, pyrimidine derivatives, etc.

[0331] According to one embodiment of the present specification, the host includes, but is not limited to, a compound represented by the following chemical formula H-1.

[0332] [Chemical Formula H-1]

[0333]

[0334] In the above chemical formula H-1,

[0335] L20 and L21 are the same or different from each other, and each independently represents a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted divalent heterocyclic group,

[0336] Ar20 and Ar21 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0337] R201 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0338] r201 is an integer from 1 to 8, and when r201 is 2 or more, 2 or more R201 are the same as or different from each other.

[0339] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently represents a direct bond; a monocyclic or polycyclic arylene group having 6 to 30 carbon atoms; or a monocyclic or polycyclic divalent heterocyclic group having 2 to 30 carbon atoms.

[0340] In one embodiment of the present specification, L20 and L21 are the same as or different from each other, and each independently represent a direct bond; a phenylene group substituted or unsubstituted with deuterium; a biphenylylene group substituted or unsubstituted with deuterium; a naphthylene group substituted or unsubstituted with deuterium; a divalent dibenzofuran group; or a divalent dibenzothiophene group.

[0341] In one embodiment of the present specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

[0342] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic heterocyclic group having 2 to 30 carbon atoms.

[0343] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic to tetracyclic aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted monocyclic to tetracyclic heterocyclic group having 6 to 20 carbon atoms.

[0344] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and each independently represent a phenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a biphenyl group unsubstituted or substituted with deuterium or a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthyl group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a thiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; a dibenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a naphthobenzofuran group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; a dibenzothiophene group unsubstituted or substituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms; Or, it is a naphthobenzothiophene group substituted or unsubstituted with a monocyclic or polycyclic aryl group having 6 to 20 carbon atoms.

[0345] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a phenyl group substituted or unsubstituted with deuterium; a biphenyl group substituted or unsubstituted with deuterium; a terphenyl group; a naphthyl group substituted or unsubstituted with deuterium; a thiophene group substituted or unsubstituted with a phenyl group; a phenanthrene group; a dibenzofuran group; a naphthobenzofuran group; a dibenzothiophene group; or a naphthobenzothiophene group.

[0346] In one embodiment of the present specification, Ar20 and Ar21 are the same as or different from each other, and are each independently a 1-naphthyl group or a 2-naphthyl group.

[0347] According to one embodiment of the present specification, the R201 is hydrogen.

[0348] According to one embodiment of the present specification, the chemical formula H-1 is represented by the following compound.

[0349]

[0350] When the light-emitting layer emits red light, phosphorescent materials such as PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium), PtOEP(octaethylporphyrin platinum), or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used as light-emitting dopants, but are not limited thereto. When the light-emitting layer emits green light, phosphorescent materials such as Ir(ppy)3(fac tris(2-phenylpyridine)iridium), or fluorescent materials such as Alq3(tris(8-hydroxyquinolino)aluminum) can be used as light-emitting dopants, but are not limited thereto. When the light-emitting layer emits blue light, a phosphorescent material such as (4,6-F2ppy)2Irpic, or a fluorescent material such as spiro-DPVBi, spiro-6P, distilbenzene (DSB), distriarylene (DSA), PFO polymer, or PPV polymer can be used as a light-emitting dopant, but is not limited thereto.

[0351] In one embodiment of the present specification, the dopant includes a compound of the following chemical formula D-1.

[0352] [Chemical Formula D-1]

[0353]

[0354] In the above chemical formula D-1,

[0355] L401 and L402 are the same or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted arylene group,

[0356] R401 to R404 are the same or different and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0357] R405 and R406 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0358] In one embodiment of the present specification, L401 and L402 are each directly connected.

[0359] In one embodiment of the present specification, R401 to R404 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0360] In one embodiment of the present specification, R401 to R404 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic aryl group; a substituted or unsubstituted polycyclic aryl group; or a substituted or unsubstituted heterocyclic group.

[0361] In one embodiment of the present specification, R401 to R404 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted pyrene group; or a substituted or unsubstituted fluorenyl group; a substituted or unsubstituted dibenzofuran group; or a substituted or unsubstituted dibenzothiophene group.

[0362] In one embodiment of the present specification, R401 to R404 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; or a substituted or unsubstituted dibenzofuran group.

[0363] In one embodiment of the present specification, R401 to R404 are the same as or different from each other, and each independently represents a phenyl group unsubstituted or substituted with an alkyl group; or a dibenzofuran group unsubstituted or substituted with an alkyl group.

[0364] In one embodiment of the present specification, R401 to R404 are the same as or different from each other, and are each independently a cyano group, a phenyl group substituted with hydrogen, or a phenyl group substituted with deuterium.

[0365] In one embodiment of the present specification, R405 and R406 are terbutyl groups.

[0366] In one embodiment of the present specification, the chemical formula D-1 is represented by the following compound.

[0367]

[0368] The above electron transport layer can play a role in facilitating electron transport. As the electron transport material, a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is suitable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The thickness of the electron transport layer may be 1 to 50 nm. When the thickness of the electron transport layer is 1 nm or more, there is an advantage in that the electron transport characteristics can be prevented from being deteriorated, and when the thickness of the electron transport layer is 50 nm or less, there is an advantage in that the driving voltage can be prevented from increasing to improve electron movement due to the electron transport layer being too thick.

[0369] The above electron injection layer can play a role in facilitating electron injection. As the electron injection material, a compound having the ability to transport electrons, an electron injection effect from the cathode, an excellent electron injection effect for the light-emitting layer or light-emitting material, a compound that prevents the movement of excitons generated in the light-emitting layer to the hole injection layer, and an excellent thin film forming ability is preferable. Specifically, examples thereof include, but are not limited to, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing 5-membered ring derivatives.

[0370] The above electron injection and transport layer can be manufactured by appropriately selecting the material used in the electron injection layer and electron transport layer.

[0371] The above electron injection and transport layer can be manufactured by using the compound of the above chemical formula 1 and the metal complex together.

[0372] The above electron injection and transport layer contains the compound of the above chemical formula 1 and the metal complex in a weight ratio of 1:10 to 10:1.

[0373] The above electron injection and transport layer contains the compound of the above chemical formula 1 and the metal complex in a weight ratio of 1:3 to 3:1.

[0374] The above metal complex compounds include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato)zinc, bis(8-hydroxyquinolinato)copper, bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h]quinolinato)beryllium, bis(10-hydroxybenzo[h]quinolinato)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)(o-cresolato)gallium, bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum, Bis(2-methyl-8-quinolinato)(2-naphtholato)gallium, etc., but are not limited thereto.

[0375] In one embodiment of the present specification, the metal complex compound is represented by the following compound.

[0376]

[0377] A hole blocking layer may be provided between the electron transport layer and the light emitting layer, and a material known in the art may be used.

[0378] The above hole blocking layer is a layer that blocks holes from reaching the cathode, and can generally be formed under the same conditions as the hole injection layer. Specifically, examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, and aluminum complexes.

[0379] The organic light-emitting device according to the present invention may be a front-emitting, back-emitting, or double-sided emitting type depending on the material used.

[0380] The organic light-emitting device of the present invention can be manufactured using a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic layers are formed using the above-described compound.

[0381] The method for preparing the compound of the above chemical formula 1 and the preparation of an organic light-emitting device using the compound are specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited by them.

[0382] In the following reaction scheme, the type and number of substituents can be appropriately selected by those skilled in the art from known starting materials, enabling the synthesis of various types of intermediates. The reaction types and reaction conditions known in the art can be utilized.

[0383] The method for preparing the compound of the above chemical formula 1 and the preparation of an organic light-emitting device using the compound are specifically described in the following examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited by them.

[0384] In the following reaction scheme, the type and number of substituents can be appropriately selected by those skilled in the art from known starting materials, enabling the synthesis of various types of intermediates. The reaction types and reaction conditions known in the art can be utilized.

[0385] Manufacturing example 1.

[0386]

[0387] 2-(2-bromo-6-chlorophenyl)-4,6-diphenyl-1,3,5-triazine (12.7 g, 30 mmol) and the above compound 1-1 (8.2 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K2CO3 (200 mL) and tetrakis(triphenylphosphine)palladium(0) (0.3 g) were added, and the mixture was stirred and refluxed for 5 hours. After cooling to room temperature, the mixture was filtered, and the resulting solid was recrystallized twice with toluene to prepare the above compound 1-2.

[0388] The above compounds 1-2 (16.41 g, 30 mmol) and 1-3 (11.66 g, 33 mmol) were added to tetrahydrofuran (300 mL). 2M K2CO3 (200 mL), Palladium acetate (0.14 g), and s-phos (2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 0.50 g) ligand were added, followed by stirring and refluxing for 5 hours. After cooling to room temperature, the resulting solid was filtered and recrystallized twice with toluene to prepare the above compound 1.

[0389] (18.45 g, yield 75%, MS:[M+H]+= 820).

[0390] Manufacturing example 2.

[0391]

[0392] Compound 2 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0393] MS: [M+H] + = 820

[0394] Manufacturing example 3.

[0395]

[0396] Compound 3 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0397] MS: [M+H] + = 820

[0398] Manufacturing example 4.

[0399]

[0400] Compound 4 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0401] MS: [M+H] + = 834

[0402] Manufacturing Example 5.

[0403]

[0404] Compound 5 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0405] MS: [M+H] + = 834

[0406] Manufacturing example 6.

[0407]

[0408] Compound 6 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0409] MS: [M+H] + = 897

[0410] Manufacturing example 7.

[0411]

[0412] Compound 7 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0413] MS: [M+H] + = 830

[0414] Manufacturing example 8.

[0415]

[0416] Compound 8 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0417] MS: [M+H] + = 820

[0418] Manufacturing example 9.

[0419]

[0420] Compound 9 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0421] MS: [M+H] + = 820

[0422] Manufacturing example 10.

[0423]

[0424] Compound 10 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0425] MS: [M+H] + = 820

[0426] Manufacturing example 11.

[0427]

[0428] Compound 11 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0429] MS: [M+H] + = 834

[0430] Manufacturing example 12.

[0431]

[0432] Compound 12 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0433] MS: [M+H] + = 834

[0434] Manufacturing example 13.

[0435]

[0436] Compound 13 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0437] MS: [M+H] + = 896

[0438] Manufacturing example 14.

[0439]

[0440] Compound 14 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0441] MS: [M+H] + = 896

[0442] Manufacturing example 15.

[0443]

[0444] Compound 15 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0445] MS: [M+H] + = 769

[0446] Manufacturing example 16.

[0447]

[0448] Compound 16 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0449] MS: [M+H] + = 857

[0450] Manufacturing example 17.

[0451]

[0452] Compound 17 was prepared in the same manner as in Manufacturing Example 1, except that each starting material was prepared as in the above reaction formula.

[0453] MS: [M+H] + = 829

[0454] [Example]

[0455] Example 1-1

[0456] A glass substrate coated with a 1000 Å thick ITO (indium tin oxide) film was placed in distilled water containing detergent and ultrasonically cleaned. The detergent was a Fischer Co. product, and the distilled water was filtered twice using a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonically cleaned twice with distilled water for 10 minutes each. After washing with distilled water, ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum deposition machine.

[0457] On the ITO transparent electrode thus prepared, the following compound HI-A was thermally vacuum deposited to a thickness of 600 Å to form a hole injection layer. On the hole injection layer, the following compound HAT at 50 Å and the following compound HT-A at 60 Å were sequentially vacuum deposited to form a first hole transport layer and a second hole transport layer.

[0458] Next, a light-emitting layer was formed by vacuum-depositing the following compounds BH and BD at a weight ratio of 25:1 to a film thickness of 200 Å on the second hole transport layer.

[0459] On the above-mentioned light-emitting layer, the previously prepared compound 1 and the following compound LiQ were vacuum-deposited at a weight ratio of 1:1 to form an electron injection and transport layer with a thickness of 350 Å. Lithium fluoride (LiF) with a thickness of 10 Å and aluminum with a thickness of 1000 Å were sequentially deposited on the electron injection and transport layer to form a cathode.

[0460]

[0461] In the above process, the deposition rate of organic materials was maintained at 0.4 Å / sec to 0.9 Å / sec, the lithium fluoride of the cathode was maintained at 0.3 Å / sec, and the aluminum was maintained at 2 Å / sec, and the vacuum during deposition was 1 × 10 -7 torr to 5 × 10 -5 torr, and an organic light-emitting device was manufactured.

[0462] Examples 1-2 to 1-17

[0463] An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that compounds 2 to 14 described in Table 1 below were used instead of compound 1 of Example 1-1.

[0464] Comparative Examples 1-1 to 1-4

[0465] An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that compounds ET-1 to ET-4 described in Table 1 below were used instead of compound 1 of Example 1-1. The structures of compounds ET-1 to ET-4 of Table 1 below are as follows.

[0466]

[0467] [Experimental Example]

[0468] 10 mA / cm for the organic light-emitting devices manufactured in Examples 1-1 to 1-17 and Comparative Examples 1-1 to 1-4 2 The driving voltage and luminous efficiency were measured at a current density of 20 mA / cm 2 The time (T90) at which the initial luminance reaches 90% of the current density was measured. The results are shown in Table 1 below.

[0469] Distinctive compound voltage (V) (@10 mA / cm) 2 )Efficiency (cd / A) (@10 mA / cm 2)Color coordinates (x, y)Lifespan (hr) (T90 at 20 mA / cm 2 ) Example 1-114.314.91(0.140, 0.092)180 Example 1-224.304.69(0.140, 0.092)190 Example 1-334.404.75(0.140, 0.092)200 Example 1-444.354.66(0.141, 0.091)205 Example 1-554.374.76(0.140, 0.092)215 Example 1-664.324.80(0.140, 0.093)205 Example 1-774.314.77(0.140, 0.091)200 Example 1-884.304.81(0.140, 0.091)210 Example 1-994.354.80(0.140, 0.092)205 Example 1-10104.394.71(0.140, 0.093)185 Example 1-11114.354.66(0.141, 0.091)205 Example 1-12124.414.50(0.141, 0.091)185 Example 1-13134.414.62(0.140, 0.093)190 Example 1-14144.454.51(0.140, 0.092)190 Example 1-15 154.5 14.61 (0.141, 0.091) 160 Example 1-16 164.3 2 4.55 (0.140, 0.093) 150 Example 1-17 174.5 0 4.51 (0.140, 0.092) 210 Comparative Example 1-1 ET-14.5 0 2.70 (0.140, 0.092) 45 Comparative Example 1-2 ET-24.5 14.11 (0.140, 0.092) 50 Comparative Example 1-3 ET-34.5 3 3.95 (0.140, 0.091) 70 Comparative Example 1-4 ET-44.4 0 4.30 (0.141, 0.093) 100

[0470] As described in Table 1 above, the compound represented by Chemical Formula 1 according to the present specification can be used in an organic layer responsible for electron injection and transport of an organic light-emitting device. As shown in Table 1 above, the compound represented by Chemical Formula 1 maximizes electron mobility by appropriately breaking conjugation within the molecule by limiting the substitution position of the linking group in the ortho direction instead of narrowing the distance between electron transport groups, and therefore, an organic light-emitting device using the compound of Chemical Formula 1 according to an exemplary embodiment of the present specification in an electron injection and transport layer exhibited excellent characteristics in terms of efficiency, driving voltage, and stability of the organic light-emitting device. In addition, by attaching quinoline or quinazoline, which are substituents with high electronegativity, a long-life characteristic was also maintained.

[0471] Specifically, Examples 1-1 to 1-17, which are organic light-emitting devices including a compound represented by Chemical Formula 1 according to one embodiment of the present specification, exhibited superior characteristics in terms of efficiency, driving voltage, and stability compared to Comparative Examples 1-1 to 1-4, which are organic light-emitting devices including a compound in which the substitution position of the connecting group is not in the ortho direction or does not include quinoline or quinazoline.

[0472] Although the preferred embodiments (electron injection and electron transport layers) of the present invention have been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims and the detailed description of the invention, and this also falls within the scope of the invention.

Claims

1. A compound of the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, R1 to R5 are the same as or different from each other, and each independently represent hydrogen; deuterium; a nitrile group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, Ar1 is a substituted or unsubstituted heteroarylene group having 6 to 20 carbon atoms and containing two or more N, Ar2 is hydrogen; deuterium; a nitrile group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, A is the following chemical formula 2-1 or chemical formula 2-2, [Chemical Formula 2-1] [Chemical Formula 2-2] In the above chemical formula 2-1 or chemical formula 2-2, * is a part that is bonded to the chemical formula 1 above, One or both of X1 to X7 are N, and the rest are CR', R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group, a and c are integers from 1 to 4, respectively, b is an integer from 1 to 3, d and e are each integers from 1 to 5, When a is 2 or more, R1 is equal to or different from each other, When b is 2 or more, R2 are equal or different, When c is 2 or greater, R3 are equal or different, When d is 2 or more, R4 are equal or different, When e is 2 or greater, R5 are equal or different.

2. In claim 1, the chemical formula 1 is a compound which is any one of the following chemical formulas 1-1 to 1-10: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] [Chemical Formula 1-10] In the above chemical formulas 1-1 to 1-10, R1 to R5, Ar1, Ar2, A, and a to e are as defined in the above chemical formula 1.

3. A compound according to claim 2, wherein R1 to R3 of chemical formulae 1-1 to 1-10 are hydrogen or deuterium.

4. In claim 1, the chemical formula 1 is a compound which is any one of the following chemical formulas 1-1-1 to 1-1-10: [Chemical Formula 1-1-1] [Chemical Formula 1-1-2] [Chemical Formula 1-1-3] [Chemical Formula 1-1-4] [Chemical Formula 1-1-5] [Chemical Formula 1-1-6] [Chemical Formula 1-1-7] [Chemical Formula 1-1-8] [Chemical Formula 1-1-9] [Chemical Formula 1-1-10] In the chemical formulas 1-1-1 to 1-1-10, R4, R5, Ar1, Ar2, A, d and e are as defined in the chemical formula 1.

5. A compound according to claim 1, wherein Ar1 is a substituted or unsubstituted divalent triazine group.

6. A compound according to claim 1, wherein Ar1 is a substituted or unsubstituted divalent pyrimidine group.

7. A compound according to claim 1, wherein Ar1 is a substituted or unsubstituted divalent imidazolyl group; or a substituted or unsubstituted divalent benzoimidazolyl group.

8. A compound according to claim 1, wherein Ar2 is an aryl group having 6 to 30 carbon atoms.

9. A compound according to claim 1, wherein R1 to R5 are each hydrogen or deuterium.

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

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

12. An organic light-emitting device according to claim 11, wherein the organic layer comprises at least one of an electron transport layer, an electron injection layer, and an electron injection and transport layer, and at least one of the layers comprises the compound.

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