Compound and organic light-emitting element comprising same

Abstract

The present specification relates to a compound of chemical formula 1, and an organic light-emitting element comprising the compound. Specifically, the compound comprises benzene substituted with chemical formulas 2 to 4, and the organic light-emitting element comprises: a first electrode; a second electrode; and at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.

Description

Compound and organic light-emitting device containing the same

[0001] This application claims the benefit of the filing dates of Korean Patent Application No. 10-2024-0086083, filed with the Korean Intellectual Property Office on July 1, 2024, and Korean Patent Application No. 10-2025-0086823, filed with the Korean Intellectual Property Office on June 30, 2025, the entire contents of which are incorporated herein by reference.

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

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

[0004] In general, organic light emitting diodes (OLEDs) are devices that utilize the organic light emitting phenomenon, typically comprising an anode and a cathode, with an organic layer between them. These organic layers are often multilayered, composed of different materials, to enhance the efficiency and stability of the device. For example, they may include 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. When a voltage is applied between the two electrodes in this device, holes are injected into the organic layer from the anode and electrons are injected into the organic layer from the cathode. Excitons form when the injected holes and electrons meet, and light is emitted when these excitons fall back to their ground state. These devices are known to exhibit 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] X1 to X6 are the same or different from each other, and are each independently CRa or C linked to any one of the following chemical formulas 2 to 4,

[0014] Ra is hydrogen or deuterium,

[0015] One of the above X1, X2 and X4 is C connected to chemical formula 2, one of the remaining Cs other than C connected to chemical formula 2 is C connected to chemical formula 3, and the remaining are C connected to chemical formula 4, or

[0016] Among the above X1, X2 and X3, one is C connected to chemical formula 2, one of the remaining Cs other than C connected to chemical formula 2 is C connected to chemical formula 3, and the rest are C connected to chemical formula 4,

[0017] [Chemical Formula 2]

[0018]

[0019] [Chemical Formula 3]

[0020]

[0021] [Chemical Formula 4]

[0022]

[0023] In the above chemical formulas 2 to 4,

[0024] R1 to R4 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,

[0025] One or both of Y1 to Y5 are N, and the rest are CRb,

[0026] Rb is hydrogen; deuterium; or a substituted or unsubstituted alkyl group,

[0027] Ar1 is a monocyclic or bicyclic, substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms, containing two Ns,

[0028] Ar2 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group,

[0029] a and b are integers from 1 to 5, respectively,

[0030] c and d are integers from 1 to 4, respectively,

[0031] When a is 2 or more, R1 are equal or different,

[0032] When b is 2 or more, R2 are equal or different,

[0033] When c is 2 or more, R3 are equal or different,

[0034] When d is 2 or more, R4 are equal or different,

[0035] is the position connected to the above chemical formula 1.

[0036] 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.

[0037] The compound of the present invention can be used as a material for an organic layer of an organic light-emitting device. When an organic light-emitting device is manufactured by including the compound of the present invention, an organic light-emitting device having high efficiency, low voltage, and long life characteristics can be obtained. In addition, when the compound of the present invention is included in an electron transport layer of an organic light-emitting device, an organic light-emitting device having long life characteristics can be manufactured by substituting a heterocycle having high intramolecular polarity in addition to triazine and pyrimidine, which play a role in transporting electrons.

[0038] Figures 1 and 2 illustrate examples of organic light-emitting devices according to the present invention.

[0039] [Explanation of symbols]

[0040] 1: Substrate

[0041] 2: Bipolar

[0042] 3: Organic layer

[0043] 4: Cathode

[0044] 5: Hole injection layer

[0045] 6: Hole transport layer

[0046] 7: Electron suppression layer

[0047] 8: Emissive layer

[0048] 9: The hole-blocking layer

[0049] 10: Electron injection and transport layer

[0050] The following describes this specification in more detail.

[0051] 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.

[0052] 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.

[0053] Examples of substituents in this specification are described below, but are not limited thereto.

[0054] 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.

[0055] 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.

[0056] Examples of the above substituents are described below, but are not limited thereto.

[0057] In this specification, examples of halogen groups include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0058] 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.

[0059] 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.

[0060] 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.

[0061] 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.

[0062] 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.

[0063] 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.

[0064] 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.

[0065] 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.

[0066] 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.

[0067] 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.

[0068] 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.

[0069] 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.

[0070] In this specification, the arylene group is as defined in the above aryl group, except that it is a divalent group.

[0071] In this specification, the heteroarylene group is as defined in the heteroaryl group above, except that it is divalent.

[0072] 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.

[0073] In the present specification, three of X1 to X6 of the chemical formula 1 are each one of chemical formulas 2 to 4, and the remainder are CRa.

[0074] In the present specification, any one of X1 to X6 of the chemical formula 1 is chemical formula 2, any one of X1 to X6 other than chemical formula 2 is chemical formula 3, and any one of X1 to X6 other than chemical formula 2 or chemical formula 3 is chemical formula 4.

[0075] In the present specification, three of X1 to X6 of Chemical Formula 1 are any one of Chemical Formulas 2 to 4, and any pair of Chemical Formulas 2 to 4 includes at least one ortho substitution position.

[0076] In this specification, the chemical formula 1 is any one of the compounds of the chemical formulas 1-1 to 1-6 below.

[0077] [Chemical Formula 1-1]

[0078]

[0079] [Chemical Formula 1-2]

[0080]

[0081] [Chemical Formula 1-3]

[0082]

[0083] [Chemical Formula 1-4]

[0084]

[0085] [Chemical Formula 1-5]

[0086]

[0087] [Chemical Formula 1-6]

[0088]

[0089] In the above chemical formulas 1-1 to 1-6, R1 to R4, Ra, Y1 to Y5, Ar1, Ar2 and a to d are as defined in the above chemical formula 1,

[0090] k is an integer from 1 to 3, and when k is 2 or greater, Ra are equal to or different from each other.

[0091] In this specification, the chemical formula 1 is any one of the compounds of the chemical formulas 1-7 to 1-9 below.

[0092] [Chemical Formula 1-7]

[0093]

[0094] [Chemical Formula 1-8]

[0095]

[0096] [Chemical Formula 1-9]

[0097]

[0098] In the above chemical formulas 1-7 to 1-9, R1 to R4, Ra, Y1 to Y5, Ar1, Ar2 and a to d are as defined in the above chemical formula 1,

[0099] k is an integer from 1 to 3, and when k is 2 or greater, Ra are equal to or different from each other.

[0100] In this specification, the chemical formula 4 is any one of the chemical formulas 4-1 to 4-3 below.

[0101] [Chemical Formula 4-1]

[0102]

[0103] [Chemical Formula 4-2]

[0104]

[0105] [Chemical Formula 4-3]

[0106]

[0107] In the above chemical formulas 4-1 to 4-3,

[0108] R4 is hydrogen; or deuterium,

[0109] One or both of Y1 to Y5 are N, and the rest are CRb,

[0110] Rb is hydrogen; deuterium; or a substituted or unsubstituted alkyl group,

[0111] d is an integer from 1 to 4,

[0112] When d is 2 or more, R4 are equal or different,

[0113] is the position connected to the above chemical formula 1.

[0114] According to one embodiment of the present specification, Ra is hydrogen or deuterium.

[0115] According to one embodiment of the present specification, Ra is hydrogen.

[0116] According to one embodiment of the present specification, Ra is deuterium.

[0117] According to one embodiment of the present specification, R1 to R4 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.

[0118] According to one embodiment of the present specification, R1 to R4 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 30 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.

[0119] According to one embodiment of the present specification, R1 to R4 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 20 carbon atoms; a substituted or unsubstituted aryl group having 6 to 20 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 20 carbon atoms.

[0120] According to one embodiment of the present specification, R1 to R4 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 10 carbon atoms; or a substituted or unsubstituted heteroaryl group having 2 to 10 carbon atoms.

[0121] According to one embodiment of the present specification, R1 to R4 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.

[0122] According to one embodiment of the present specification, R1 to R4 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.

[0123] According to one embodiment of the present specification, R1 to R4 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 phenyl group, a naphthyl group, or a terbutyl group.

[0124] According to one embodiment of the present specification, R1 to R4 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.

[0125] According to one embodiment of the present specification, R1 to R4 are the same as or different from each other, and are each independently hydrogen, deuterium, a phenyl group, or a naphthyl group.

[0126] According to one embodiment of the present specification, R1 to R4 are hydrogen or deuterium.

[0127] According to one embodiment of the present specification, all of R1 to R4 are hydrogen.

[0128] According to one embodiment of the present specification, one or both of Y1 to Y5 are N, the others are CRb, and Rb is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0129] According to one embodiment of the present specification, one of Y1 to Y5 is N, the other is CRb, and Rb is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0130] According to one embodiment of the present specification, any two of Y1 to Y5 are N, the others are CRb, and Rb is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0131] According to one embodiment of the present specification, one or both of Y1 to Y5 are N, the others are CRb, and Rb is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0132] According to one embodiment of the present specification, one or both of Y1 to Y5 are N, the others are CRb, and Rb is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0133] According to one embodiment of the present specification, one or both of Y1 to Y5 are N, the others are CRb, and Rb is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0134] According to one embodiment of the present specification, one or both of Y1 to Y5 are N, the others are CRb, and Rb is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms.

[0135] According to one embodiment of the present specification, one or both of Y1 to Y5 are N and the others are CRb, and Rb is hydrogen; deuterium; or a methyl group.

[0136] According to one embodiment of the present specification, one or both of Y1 to Y5 are N, the others are CRb, and Rb is hydrogen or deuterium.

[0137] According to one embodiment of the present specification, one of Y1 to Y5 is N and the other is CRb, and Rb is hydrogen; deuterium; or a methyl group.

[0138] According to one embodiment of the present specification, among Y1 to Y5, Y1 is N, the others are CRb, and Rb is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0139] According to one embodiment of the present specification, among Y1 to Y5, Y2 is N, the others are CRb, and Rb is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0140] According to one embodiment of the present specification, among Y1 to Y5, Y3 is N, the rest are CRb, and Rb is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0141] According to one embodiment of the present specification, among Y1 to Y5, Y4 is N, the rest are CRb, and Rb is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0142] According to one embodiment of the present specification, Rb is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0143] According to one embodiment of the present specification, Rb is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0144] According to one embodiment of the present specification, Rb is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0145] According to one embodiment of the present specification, Rb is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0146] According to one embodiment of the present specification, Rb is hydrogen; deuterium; a methyl group; an ethyl group; or a propyl group.

[0147] According to one embodiment of the present specification, Ar1 is a monocyclic or bicyclic, substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms, containing two Ns.

[0148] According to one embodiment of the present specification, Ar1 is a monocyclic or bicyclic, substituted or unsubstituted heteroarylene group having 2 to 15 carbon atoms, containing two Ns.

[0149] According to one embodiment of the present specification, Ar1 is a monocyclic or bicyclic, substituted or unsubstituted heteroarylene group having 2 to 10 carbon atoms, containing two Ns.

[0150] According to one embodiment of the present specification, Ar1 is a heteroarylene group having 2 to 20 carbon atoms, which is monocyclic or bicyclic and contains two Ns and is substituted or unsubstituted with one or more groups selected from the group consisting of hydrogen, deuterium, an alkyl group, and an aryl group, or two or more linked groups.

[0151] According to one embodiment of the present specification, Ar1 is a heteroarylene group having 2 to 20 carbon atoms, which is monocyclic or bicyclic and contains two Ns and is substituted or unsubstituted with one or more groups selected from the group consisting of hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 30 carbon atoms, or two or more linked groups.

[0152] According to one embodiment of the present specification, Ar1 is a heteroarylene group having 2 to 20 carbon atoms, which is monocyclic or bicyclic and contains two Ns and is substituted or unsubstituted with one or more groups selected from the group consisting of hydrogen, deuterium, an alkyl group having 1 to 5 carbon atoms and an aryl group having 6 to 20 carbon atoms, or two or more linked groups.

[0153] According to one embodiment of the present specification, Ar1 is a heteroarylene group having 2 to 20 carbon atoms, which is monocyclic or bicyclic and contains two Ns and is substituted or unsubstituted with one or more groups selected from the group consisting of hydrogen, deuterium, an alkyl group having 1 to 3 carbon atoms and an aryl group having 6 to 10 carbon atoms, or two or more linked groups.

[0154] According to one embodiment of the present specification, Ar1 is a heteroarylene group having 2 to 20 carbon atoms, which is monocyclic or bicyclic and contains two Ns and is substituted or unsubstituted with one or more groups selected from the group consisting of hydrogen, deuterium, a methyl group, an ethyl group, a propyl group, a butyl group, and a phenyl group, or two or more linked groups.

[0155] According to one embodiment of the present specification, Ar1 is a substituted or unsubstituted divalent pyrimidinyl group; a substituted or unsubstituted divalent pyridazinyl group; a substituted or unsubstituted divalent imidazolyl group; a substituted or unsubstituted divalent pyrazolyl group; a substituted or unsubstituted divalent diazinyl group; a substituted or unsubstituted divalent pyrazinyl group; a substituted or unsubstituted divalent quinazolyl group; a substituted or unsubstituted divalent quinoxalyl group; or a substituted or unsubstituted divalent benzoimidazolyl group.

[0156] According to one embodiment of the present specification, Ar1 is a divalent pyrimidinyl group substituted or unsubstituted with one or more groups selected from the group consisting of hydrogen, deuterium, an alkyl group, and an aryl group, or two or more linked groups; a divalent pyridazinyl group substituted or unsubstituted with one or more groups selected from the group consisting of hydrogen, deuterium, an alkyl group, and an aryl group, or two or more linked groups; a divalent imidazolyl group substituted or unsubstituted with one or more groups selected from the group consisting of hydrogen, deuterium, an alkyl group, and an aryl group, or two or more linked groups; a divalent pyrazolyl group substituted or unsubstituted with one or more groups selected from the group consisting of hydrogen, deuterium, an alkyl group, and an aryl group, or two or more linked groups; a divalent diazinyl group substituted or unsubstituted with one or more groups selected from the group consisting of hydrogen, deuterium, an alkyl group, and an aryl group, or two or more linked groups; A divalent pyrazinyl group unsubstituted or substituted with one or more groups selected from the group consisting of hydrogen, deuterium, an alkyl group, and an aryl group, or two or more linked groups; a divalent quinazolyl group unsubstituted or substituted with one or more groups selected from the group consisting of hydrogen, deuterium, an alkyl group, and an aryl group, or two or more linked groups; a divalent quinoxalyl group unsubstituted or substituted with one or more groups selected from the group consisting of hydrogen, deuterium, an alkyl group, and an aryl group, or two or more linked groups; or a divalent benzoimidazolyl group unsubstituted or substituted with one or more groups selected from the group consisting of hydrogen, deuterium, an alkyl group, and an aryl group.

[0157] According to one embodiment of the present specification, the Ar1 is a divalent pyrimidinyl group substituted or unsubstituted with one or more groups selected from the group consisting of hydrogen, deuterium, a methyl group, an ethyl group, a propyl group, a butyl group, and a phenyl group, or two or more linked groups; a divalent pyridazinyl group substituted or unsubstituted with one or more groups selected from the group consisting of hydrogen, deuterium, a methyl group, an ethyl group, a propyl group, a butyl group, and a phenyl group, or two or more linked groups; a divalent imidazolyl group substituted or unsubstituted with one or more groups selected from the group consisting of hydrogen, deuterium, a methyl group, an ethyl group, a propyl group, a butyl group, and a phenyl group, or two or more linked groups; a divalent pyrazolyl group substituted or unsubstituted with one or more groups selected from the group consisting of hydrogen, deuterium, a methyl group, an ethyl group, a propyl group, a butyl group, and a phenyl group, or two or more linked groups; A divalent diazinyl group unsubstituted or substituted with one or more groups selected from the group consisting of hydrogen, deuterium, a methyl group, an ethyl group, a propyl group, a butyl group, and a phenyl group, or two or more linked groups; A divalent pyrazinyl group unsubstituted or substituted with one or more groups selected from the group consisting of hydrogen, deuterium, a methyl group, an ethyl group, a propyl group, a butyl group, and a phenyl group, or two or more linked groups; A divalent quinazolyl group unsubstituted or substituted with one or more groups selected from the group consisting of hydrogen, deuterium, a methyl group, an ethyl group, a propyl group, a butyl group, and a phenyl group, or two or more linked groups; A divalent quinoxalyl group unsubstituted or substituted with one or more groups selected from the group consisting of hydrogen, deuterium, a methyl group, an ethyl group, a propyl group, a butyl group, and a phenyl group; Or a divalent benzimidazolyl group substituted or unsubstituted with one or more groups selected from the group consisting of hydrogen, deuterium, methyl, ethyl, propyl, butyl, and phenyl groups, or two or more linked groups.

[0158] According to one embodiment of the present specification, Ar2 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group.

[0159] According to one embodiment of the present specification, Ar2 is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0160] According to one embodiment of the present specification, Ar2 is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0161] According to one embodiment of the present specification, Ar2 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 10 carbon atoms.

[0162] According to one embodiment of the present specification, Ar2 is hydrogen; deuterium; an alkyl group having 1 to 30 carbon atoms substituted or unsubstituted with one or more groups selected from the group consisting of hydrogen, deuterium, an alkyl group, and an aryl 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 hydrogen, deuterium, an alkyl group, and an aryl group.

[0163] According to one embodiment of the present specification, Ar2 is hydrogen; deuterium; an alkyl group having 1 to 20 carbon atoms substituted or unsubstituted with one or more groups selected from the group consisting of hydrogen, deuterium, an alkyl group, and an aryl 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 hydrogen, deuterium, an alkyl group, and an aryl group.

[0164] According to one embodiment of the present specification, Ar2 is hydrogen; deuterium; an alkyl group having 1 to 10 carbon atoms substituted or unsubstituted with one or more groups selected from the group consisting of hydrogen, deuterium, an alkyl group, and an aryl group, or two or more linked groups; or an aryl group having 6 to 10 carbon atoms substituted or unsubstituted with one or more groups selected from the group consisting of hydrogen, deuterium, an alkyl group, and an aryl group.

[0165] According to one embodiment of the present specification, Ar2 is hydrogen; deuterium; a methyl group; an ethyl group; a propyl group; a butyl group; or a phenyl group.

[0166] According to one embodiment of the present specification, Ar2 is hydrogen; deuterium or a phenyl group.

[0167] In one embodiment of the present specification, a is an integer from 1 to 5.

[0168] In one embodiment of the present specification, a is 5.

[0169] In one embodiment of the present specification, a is 4.

[0170] In one embodiment of the present specification, a is 3.

[0171] In one embodiment of the present specification, a is 2.

[0172] In one embodiment of the present specification, a is 1.

[0173] In one embodiment of the present specification, b is an integer from 1 to 5.

[0174] In one embodiment of the present specification, b is 5.

[0175] In one embodiment of the present specification, b is 4.

[0176] In one embodiment of the present specification, b is 3.

[0177] In one embodiment of the present specification, b is 2.

[0178] In one embodiment of the present specification, b is 1.

[0179] In one embodiment of the present specification, c is an integer from 1 to 4.

[0180] In one embodiment of the present specification, c is 4.

[0181] In one embodiment of the present specification, c is 3.

[0182] In one embodiment of the present specification, c is 2.

[0183] In one embodiment of the present specification, c is 1.

[0184] In one embodiment of the present specification, d is an integer from 1 to 4.

[0185] In one embodiment of the present specification, d is 4.

[0186] In one embodiment of the present specification, d is 3.

[0187] In one embodiment of the present specification, d is 2.

[0188] In one embodiment of the present specification, d is 1.

[0189] In one embodiment of the present specification, the chemical formula 1 is a compound having any one of the following structural formulas.

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203] The substituents 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 substituents can be changed according to a technique known in the art.

[0204] 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.

[0205] 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, characterized in that one or more of the organic layers includes the compound described above.

[0206] 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.

[0207] 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.

[0208] 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.

[0209] 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.

[0210] 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.

[0211] In the organic light-emitting device of the present invention, the electron injection and transport layer includes a compound of the above chemical formula 1 and a metal complex.

[0212] 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.

[0213] 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.

[0214] In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

[0215] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0216] (1) Anode / hole transport layer / light emitting layer / cathode

[0217] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0218] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0219] (4) Anode / hole transport layer / light emitting layer / electron transport layer / cathode

[0220] (5) Anode / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0221] (6) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0222] (7) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0223] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0224] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0225] (10) Anode / hole transport layer / electron suppression layer / light emitting layer / electron transport layer / cathode

[0226] (11) Anode / hole transport layer / electron suppression layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0227] (12) Anode / hole injection layer / hole transport layer / electron suppression layer / light emitting layer / electron transport layer / cathode

[0228] (13) Anode / hole injection layer / hole transport layer / electron suppression layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0229] (14) Anode / hole transport layer / light emitting layer / hole suppression layer / electron transport layer / cathode

[0230] (15) Anode / hole transport layer / light emitting layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0231] (16) Anode / hole injection layer / hole transport layer / light emitting layer / hole suppression layer / electron transport layer / cathode

[0232] (17) Anode / hole injection layer / hole transport layer / light emitting layer / hole suppression layer / electron transport layer / electron injection layer / cathode

[0233] (18) Anode / hole injection layer / hole transport layer / electron suppression layer / light-emitting layer / hole blocking layer / electron injection and transport layer / cathode

[0234] 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.

[0235] 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).

[0236] 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 suppression 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).

[0237] 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.

[0238] 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.

[0239] 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.

[0240] 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.

[0241] 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 nm 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.

[0242] 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.

[0243] [Chemical formula HI-1]

[0244]

[0245] In the above chemical formula HI-1,

[0246] R400 to R402 are the same or different, and each independently represent one selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted amine group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or combine with adjacent groups to form a substituted or unsubstituted ring,

[0247] L402 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

[0248] According to one embodiment of the present specification, R400 to R402 are the same as or different from each other, and are each independently one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted amine group; a substituted or unsubstituted heteroaryl group; and combinations thereof.

[0249] According to one embodiment of the present specification, R402 is any one selected from the group consisting of a phenyl group substituted with a carbazole group or an arylamine group; a biphenyl group substituted with a carbazole group or an arylamine group; and combinations thereof.

[0250] According to one embodiment of the present specification, R400 and R401 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group, or are bonded to an adjacent group to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0251] According to one embodiment of the present specification, R400 and R401 are the same as or different from each other, and each independently represents an aryl group substituted or unsubstituted with an alkyl group.

[0252] According to one embodiment of the present specification, R400 and R401 are the same as or different from each other, and each independently represents a phenyl group or a dimethylfluorene group.

[0253] According to one embodiment of the present specification, the chemical formula HI-1 is represented by the following compound.

[0254]

[0255] 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-2.

[0256] [Chemical formula HI-2]

[0257]

[0258] In the above chemical formula HI-2,

[0259] R301 to R303 are the same or different and are each independently hydrogen; deuterium; or a halogen group,

[0260] r301 to r303 are integers from 1 to 4, and when r301 to r303 are 2 or more, the substituents in each parenthesis are the same or different.

[0261] According to one embodiment of the present specification, R301 to R303 are F.

[0262] According to one embodiment of the present specification, the chemical formula HI-2 is represented by the following compound.

[0263]

[0264] 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 having 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.

[0265] According to one embodiment of the present specification, the hole transport layer includes, but is not limited to, a compound represented by the following chemical formula HT-2.

[0266] [Chemical formula HT-2]

[0267]

[0268] In the above chemical formula HT-2,

[0269] R403 to R406 are the same or different, and each independently represent one selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted amine group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or combine with adjacent groups to form a substituted or unsubstituted ring,

[0270] L403 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group,

[0271] l403 is an integer from 1 to 3, and if l403 is 2 or greater, L403 are equal to or different from each other.

[0272] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and each independently is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted amine group; a substituted or unsubstituted heteroaryl group; and combinations thereof.

[0273] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and each independently represents an aryl group having 6 to 30 carbon atoms.

[0274] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, or a naphthyl group.

[0275] According to one embodiment of the present specification, R403 to R406 are the same as or different from each other, and each independently is a phenyl group.

[0276] According to one embodiment of the present specification, the L403 is an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 3 to 30 carbon atoms substituted with an arylene group.

[0277] According to one embodiment of the present specification, the L403 is a divalent carbazole group substituted or unsubstituted with a phenylene group, a divalent biphenyl group, or an aryl group.

[0278] According to one embodiment of the present specification, the chemical formula HT-2 is represented by the following compound.

[0279]

[0280] 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.

[0281] According to one embodiment of the present specification, the electron suppression layer includes, but is not limited to, a compound represented by the following chemical formula EB-1.

[0282] [Chemical formula EB-1]

[0283]

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

[0285] R407 to R409 are the same or different, and each independently represent one selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted amine group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or combine with adjacent groups to form a substituted or unsubstituted ring,

[0286] L404 is a substituted or unsubstituted arylene group, or a substituted or unsubstituted heteroarylene group.

[0287] L404 is a phenylene group.

[0288] According to one embodiment of the present specification, R407 to R409 are the same as or different from each other, and are each independently one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted amine group; a substituted or unsubstituted heteroaryl group; and combinations thereof.

[0289] According to one embodiment of the present specification, R409 is a carbazole group substituted or unsubstituted with a phenyl group.

[0290] According to one embodiment of the present specification, R407 and R408 are the same as or different from each other, and each independently represents an aryl group substituted or unsubstituted with an alkyl group, or are bonded to an adjacent group to form an aromatic hydrocarbon ring substituted with an alkyl group.

[0291] According to one embodiment of the present specification, R407 and R408 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, or a dimethylfluorene group.

[0292] According to one embodiment of the present disclosure, the chemical formula EB-1 is selected from the following compounds.

[0293]

[0294] 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 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.

[0295] 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.

[0296] 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.

[0297] [Chemical Formula H-1]

[0298]

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

[0300] 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,

[0301] 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,

[0302] 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,

[0303] 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.

[0304] 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.

[0305] 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.

[0306] In one embodiment of the present specification, Ar20 is a substituted or unsubstituted heterocyclic group, and Ar21 is a substituted or unsubstituted aryl group.

[0307] 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.

[0308] 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.

[0309] 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.

[0310] 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.

[0311] 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.

[0312] According to one embodiment of the present specification, the R201 is hydrogen.

[0313] According to one embodiment of the present specification, the chemical formula H-1 is represented by the following compound.

[0314]

[0315] 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.

[0316] According to one embodiment of the present specification, the dopant is represented by a compound represented by the following chemical formula D-1.

[0317] [Chemical Formula D-1]

[0318]

[0319] In the above chemical formula D-1,

[0320] T1 to T5 are the same or different and are each independently hydrogen; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; or a substituted or unsubstituted aryl group,

[0321] t3 and t4 are integers from 1 to 4, respectively.

[0322] t5 is an integer from 1 to 3,

[0323] If the above t3 is 2 or more, the above 2 or more T3 are the same or different from each other,

[0324] If the above t4 is 2 or more, the two or more T4 are the same or different from each other,

[0325] When the above t5 is 2 or more, the two or more T5 are the same or different from each other.

[0326] According to one embodiment of the present specification, T1 to T5 are the same as or different from each other, and each independently represents hydrogen; a substituted or unsubstituted straight-chain or branched-chain alkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms.

[0327] According to one embodiment of the present specification, T1 to T5 are the same as or different from each other, and each independently represents hydrogen; a straight or branched alkyl group having 1 to 30 carbon atoms; a monocyclic or polycyclic arylamine group having 6 to 30 carbon atoms; or a monocyclic or polycyclic aryl group having 6 to 30 carbon atoms which is unsubstituted or substituted with a straight or branched alkyl group having 1 to 30 carbon atoms.

[0328] According to one embodiment of the present specification, T1 to T5 are the same as or different from each other, and are each independently hydrogen; a methyl group; an isopropyl group; a diphenylamine group; or a phenyl group substituted or unsubstituted with a methyl group or an isopropyl group.

[0329] According to one embodiment of the present specification, T1 to T5 are the same as or different from each other, and each independently represents an isopropyl group; or a phenyl group substituted or unsubstituted with an isopropyl group.

[0330] According to one embodiment of the present specification, the chemical formula D-1 is represented by the compound below.

[0331]

[0332] 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.

[0333] According to one embodiment of the present specification, the hole-blocking layer includes a compound of the following chemical formula HB-1.

[0334] [Chemical formula HB-1]

[0335]

[0336] In the above chemical formula HB-1,

[0337] At least one of Z1 to Z3 is N, and the rest are CH,

[0338] L601 is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group,

[0339] Ar601 to Ar603 are the same or different, and each independently represents a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0340] According to one embodiment of the present specification, the L601 is a substituted or unsubstituted monocyclic or polycyclic arylene group having 6 to 30 carbon atoms.

[0341] According to one embodiment of the present specification, the L601 is a phenylene group; a biphenylylene group; or a naphthylene group.

[0342] According to one embodiment of the present specification, Ar601 to Ar603 are the same as or different from each other, and are each independently a substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.

[0343] According to one embodiment of the present specification, Ar601 to Ar603 are a phenyl group or a dimethylfluorene group.

[0344] According to one embodiment of the present specification, the chemical formula HB-1 is represented by the following compound.

[0345]

[0346] 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 nm 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.

[0347] 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. Specific 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.

[0348] 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.

[0349] 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.

[0350] 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.

[0351] 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.

[0352] 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.

[0353] 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.

[0354] 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.

[0355] 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.

[0356] 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.

[0357] 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.

[0358] 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.

[0359] 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.

[0360] Manufacturing Example 1. Synthesis of Chemical Formula E1

[0361]

[0362] The above compounds 2-(5-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine (10.0 g, 15.4 mmol) and (3-(pyridin-3-yl)phenyl)boronic acid (3.06 g, 15.4 mmol) were completely dissolved in tetrahydrofuran (100 ml), then potassium carbonate (6.38 g, 46.1 mmol) dissolved in 20 ml of water was added, and tetrakistriphenylphosphinepalladium (533 mg, 0.5 mmol) dissolved in tetrahydrofuran was slowly added. After lowering the temperature to room temperature and terminating the reaction, the potassium carbonate solution was removed and the above white solid was filtered. The filtered white solid was washed twice with water and ethyl acetate, respectively, to produce the compound of the above chemical formula E1 (10.5 g, yield 89%).

[0363] MS[M+H] + = 769

[0364] Manufacturing Example 2. Synthesis of Chemical Formula E2

[0365]

[0366] A compound of the above chemical formula E2 was prepared in the same manner as in Manufacturing Example 1, except that (3-(pyridin-4-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid in Manufacturing Example 1.

[0367] MS[M+H] + = 769

[0368] Manufacturing Example 3. Synthesis of Chemical Formula E3

[0369]

[0370] A compound of the above chemical formula E3 was prepared in the same manner as in Preparation Example 2, except that 2-(5-chloro-2'-(2,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(5-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine in Preparation Example 2.

[0371] MS[M+H] + = 769

[0372] Manufacturing Example 4. Synthesis of Chemical Formula E4

[0373]

[0374] In Manufacturing Example 1, 2-(3-chloro-2'-(2,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine was used instead of the compound 2-(5-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine, and (4-(pyridin-4-yl)phenyl)boronic acid was used instead of (3-(pyridin-3-yl)phenyl)boronic acid, and a compound of the chemical formula E4 was prepared in the same manner as in Manufacturing Example 1.

[0375] MS[M+H] + = 769

[0376] Manufacturing Example 5. Synthesis of Chemical Formula E5

[0377]

[0378] A compound of the above chemical formula E5 was prepared in the same manner as in Preparation Example 1, except that 2-(3-chloro-2'-(2,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine was used instead of the compound 2-(5-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine in Preparation Example 1.

[0379] MS[M+H] + = 769

[0380] Manufacturing Example 6. Synthesis of Chemical Formula E6

[0381]

[0382] A compound of the above chemical formula E6 was prepared in the same manner as in Preparation Example 1, except that 2-(4-chloro-2'-(2,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine was used instead of the compound 2-(5-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine in Preparation Example 1.

[0383] MS[M+H] + = 769

[0384] Manufacturing Example 7. Synthesis of Chemical Formula E7

[0385]

[0386] In Preparation Example 1, 2-(4-chloro-2'-(2,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(5-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine, and (3-(pyridin-2-yl)phenyl)boronic acid was used instead of (3-(pyridin-3-yl)phenyl)boronic acid, and a compound of the above chemical formula E7 was prepared in the same manner as in Preparation Example 1.

[0387] MS[M+H] + = 769

[0388] Manufacturing Example 8. Synthesis of Chemical Formula E8

[0389]

[0390] A compound of the above chemical formula E8 was prepared in the same manner as in Preparation Example 1, except that 2-(4-chloro-2'-(2,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of the compound 2-(5-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine in Preparation Example 1.

[0391] MS[M+H] + = 769

[0392] Manufacturing Example 9. Synthesis of Chemical Formula E9

[0393]

[0394] A compound of the chemical formula E9 was prepared in the same manner as in Preparation Example 1, except that 2-(6-chloro-2'-(2,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of the compound 2-(5-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine in Preparation Example 1.

[0395] MS[M+H] + = 769

[0396] Manufacturing Example 10. Synthesis of Chemical Formula E10

[0397]

[0398] A compound of the chemical formula E10 was prepared in the same manner as in Preparation Example 1, except that 2-(2-chloro-2'-(2,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine was used instead of the compound 2-(5-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine in Preparation Example 1.

[0399] MS[M+H] + = 769

[0400] Manufacturing Example 11. Synthesis of Chemical Formula E11

[0401]

[0402] In Manufacturing Example 1, 2-(2-chloro-2'-(2,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine was used instead of the compound 2-(5-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine, and (3-(pyridin-4-yl)phenyl)boronic acid was used instead of (3-(pyridin-3-yl)phenyl)boronic acid, and a compound of the chemical formula E11 was prepared in the same manner as in Manufacturing Example 1.

[0403] MS[M+H] + = 769

[0404] Manufacturing Example 12. Synthesis of Chemical Formula E12

[0405]

[0406] In Manufacturing Example 1, 2-(5-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine was used instead of the compound 2-(5-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine, and (2-(pyridin-3-yl)phenyl)boronic acid was used instead of (3-(pyridin-3-yl)phenyl)boronic acid, and a compound of the chemical formula E12 was prepared in the same manner as in Manufacturing Example 1.

[0407] MS[M+H] + = 769

[0408] Manufacturing Example 13. Synthesis of Chemical Formula E13

[0409]

[0410] In Manufacturing Example 1, the compound of formula E13 was manufactured in the same manner as in Manufacturing Example 1, except that 2-(3-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine was used instead of the compound 2-(5-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine.

[0411] MS[M+H] + = 769

[0412] Manufacturing Example 14. Synthesis of Chemical Formula E14

[0413]

[0414] In Manufacturing Example 1, the compound 2-(5-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine was replaced with 2-(2-chloro-2'-(2,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine, and (3-(pyridin-3-yl)phenyl)boronic acid was replaced with (3-(pyridin-4-yl)phenyl)boronic acid, except that the compound of the chemical formula E14 was prepared in the same manner as in Manufacturing Example 1.

[0415] MS[M+H] + = 769

[0416] Manufacturing Example 15. Synthesis of Chemical Formula E15

[0417]

[0418] In Manufacturing Example 1, the compound of the chemical formula E15 was manufactured in the same manner as in Manufacturing Example 1, except that 2-(5'-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine was replaced with 2-(5'-chloro-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-4-phenylquinazoline.

[0419] MS[M+H] + = 743

[0420] Manufacturing Example 16. Synthesis of Chemical Formula E16

[0421]

[0422] A compound of the chemical formula E16 was prepared in the same manner as in Preparation Example 1, except that 4-(5'-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine was replaced with 4-(5'-chloro-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-2-phenylquinazoline.

[0423] MS[M+H] + = 743

[0424] Manufacturing Example 17. Synthesis of Chemical Formula E17

[0425]

[0426] In Manufacturing Example 1, the compound 2-(5-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine was replaced with 2-(4-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine, and (3-(pyridin-3-yl-d4)phenyl)boronic acid was replaced with (3-(pyridin-3-yl)phenyl)boronic acid, except that the compound of the chemical formula E17 was prepared in the same manner as in Manufacturing Example 1.

[0427] MS[M+H] + = 773

[0428] Manufacturing Example 18. Synthesis of Chemical Formula E18

[0429]

[0430] In Manufacturing Example 1, the compound 2-(5-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine was replaced with 2-(3-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-4-yl)-4,6-diphenyl-1,3,5-triazine, and (3-(2,6-dimethylpyridin-4-yl)phenyl)boronic acid was replaced with (3-(pyridin-3-yl)phenyl)boronic acid, except that a compound of the chemical formula E18 was manufactured in the same manner as in Manufacturing Example 1.

[0431] MS[M+H] + = 797

[0432] Manufacturing Example 19. Synthesis of Chemical Formula E19

[0433]

[0434] A compound of the chemical formula E19 was prepared in the same manner as in Manufacturing Example 4, except that (4-(pyridin-2-yl)phenyl)boronic acid was used instead of (4-(pyridin-4-yl)phenyl)boronic acid in Manufacturing Example 4.

[0435] MS[M+H] + = 769

[0436] Manufacturing Example 20. Synthesis of Chemical Formula E20

[0437]

[0438] In Preparation Example 1, 2-(5-chloro-2'-(4,6-diphenylpyrimidin-2-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine was used instead of 2-(6-chloro-2'-(2,6-diphenylpyrimidin-4-yl)-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine, and (4-(pyridin-3-yl)phenyl)boronic acid was used instead of (3-(pyridin-3-yl)phenyl)boronic acid, and a compound of the above chemical formula E20 was prepared in the same manner as in Preparation Example 1.

[0439] MS[M+H] + = 769

[0440] Example 1-1.

[0441] A glass substrate coated with a 1,000 Å thick ITO (indium tin oxide) film was placed in distilled water containing detergent and ultrasonically cleaned. The detergent was a Fischer Co. product, and the distilled water was secondarily filtered through a Millipore Co. filter. After washing the ITO for 30 minutes, ultrasonically cleaned twice with distilled water for 10 minutes each. After washing with distilled water, ultrasonically cleaned with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transferred to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using oxygen plasma and then transferred to a vacuum deposition machine.

[0442] On the ITO transparent electrode prepared in this way, a hole injection layer was formed by thermally vacuum depositing the compounds HI1 and HI2 below at a ratio of 98:2 (molar ratio) to a thickness of 100 Å. On the hole injection layer, a compound represented by the chemical formula HT1 (1150 Å) was vacuum deposited to form a hole transport layer. Subsequently, an electron blocking layer was formed by vacuum depositing a compound EB1 on the hole transport layer to a film thickness of 50 Å. Subsequently, a light emitting layer was formed by vacuum depositing a compound represented by the chemical formula BH below and a compound represented by the chemical formula BD below at a weight ratio of 50:1 to a film thickness of 200 Å on the electron blocking layer. A hole blocking layer was formed by vacuum depositing a compound represented by the chemical formula HB1 below at a film thickness of 50 Å on the light emitting layer. Next, a compound represented by the following chemical formula E1 and a compound represented by the following chemical formula LiQ were vacuum-deposited at a weight ratio of 1:1 on the hole-blocking layer to form an electron injection and transport layer with a thickness of 30 Å. Lithium fluoride (LiF) was sequentially deposited with a thickness of 12 Å and aluminum was sequentially deposited with a thickness of 1,000 Å on the electron injection and transport layer to form a cathode.

[0443]

[0444] In the above process, the deposition rate of organic materials was maintained at 0.4 to 0.7 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 2x10 -7 ~ 5x10 -6 Torr was maintained, and an organic light-emitting device was fabricated.

[0445] Examples 1-2 to 1-20.

[0446] An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound described in Table 1 below was used instead of compound E1 of Example 1.

[0447] Comparative Examples 1-1 to 1-5

[0448] An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compounds described in Table 1 below were used instead of Compound E1. The compounds ETL-1 to ETL-5 used in Table 1 below are as follows.

[0449]

[0450] When current was applied to the organic light-emitting devices manufactured by Examples 1-1 to 1-20 and Comparative Examples 1-1 to 1-5, the voltage, efficiency, color coordinates, and lifespan were measured, and the results are shown in [Table 1] below. T95 refers to the time required for the luminance to decrease from the initial luminance (1600 nit) to 95%.

[0451] Compound (electron injection and transport layer) voltage V@20mA / cm 2 )Efficiency (cd / A@20mA / cm 2) Color coordinates (x, y) T95 (hr) Example 1-1 Compound E1 3.78 6.18 (0.140, 0.040) 256 Example 1-2 Compound E2 3.72 6.22 (0.139, 0.039) 249 Example 1-3 Compound E3 3.73 6.24 (0.140, 0.039) 251 Example 1-4 Compound E4 3.81 6.21 (0.140, 0.040) 255 Example 1-5 Compound E5 3.83 6.23 (0.141, 0.039) 247 Example 1-6 Compound E6 3.79 6.35 (0.140, 0.041) 250 Example 1-7 Compound E7 3.8 16.38 (0.139, 0.039) 248 Example 1-8 Compound E8 3.8 8 6.42 (0.140, 0.040) 246 Example 1-9 Compound E9 3.9 16.41 (0.140, 0.040) 251 Example 1-10 Compound E10 3.8 4 6.34 (0.140, 0.041) 244 Example 1-11 Compound E11 3.9 2 6.32 (0.141, 0.040) 249 Example 1-12 Compound E12 3.8 6.26 (0.140, 0.041) 257 Example 1-13 Compound E133.83 6.30 (0.140, 0.040) 252 Example 1-14 Compound E143.96 6.29 (0.139, 0.041) 249 Example 1-15 Compound E153.77 6.37 (0.140, 0.039) 250 Example 1-16 Compound E163.82 6.32 (0.139, 0.040) 257 Example 1-17 Compound E173.87 6.26 (0.140, 0.040) 246 Example 1-18 Compound E183.93 6.33 (0.141, 0.040) 242 Example 1-19 Compound E19 3.83 6.19 (0.140, 0.041) 259 Example 1-20 Compound E20 3.87 6.24 (0.140, 0.040) 263 Comparative Example 1-1 ETL-14.66 5.06 (0.140, 0.039) 182 Comparative Example 1-2 ETL-24.71 5.15 (0.140, 0.040) 176 Comparative Example 1-3 ETL-34.40 5.49 (0.139, 0.040) 154 Comparative Example 1-4 ETL-44.58 4.91 (0.140, 0.039) 174 Comparative Example 1-5 ETL-54.42 5.63 (0.140, 0.039)159

[0452] As shown in Table 1 above, the organic light-emitting devices of Examples 1-1 to 1-20 manufactured using the compounds of the present invention, in which chemical formulae 2 to 4 are substituted at positions X1, X2 and X4 of Chemical Formula 1 or positions X1, X2 and X3 of Chemical Formula 1, as electron injection and transport layers, exhibit excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic light-emitting devices.

[0453] On the other hand, in the case of the organic light-emitting devices of Comparative Examples 1-1 to 1-5 using compounds in which triazine or N-containing ring groups were substituted at positions X1, X3, and X5 of Chemical Formula 1, the voltage was increased and the efficiency or stability (lifespan) was decreased compared to the organic light-emitting devices of Examples 1-1 to 1-20 using compounds according to Chemical Formula 1 of the present invention.

[0454] Compared to the electron injection and transport layers commonly used, the electron mobility was increased through a combination of a triazine ring and a pyrimidine or other N-containing ring group with relatively good electron mobility, thereby securing high efficiency and low voltage characteristics. In addition, by inserting a heterocyclic group between the connecting groups, the electron mobility was appropriately controlled, thereby securing the lifespan.

[0455] In addition, by substituting chemical formulae 2 to 4 at positions X1, X2 and X4 of chemical formula 1 or positions X1, X2 and X3 of chemical formula 1, the electronic conjugation was appropriately interrupted due to the ortho-bent linking group, thereby enabling the organic light-emitting device to exhibit excellent voltage, efficiency or lifespan effects.

[0456] 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, X1 to X6 are the same or different from each other, and are each independently CRa or C linked to any one of the following chemical formulas 2 to 4, Ra is hydrogen or deuterium, One of the above X1, X2 and X4 is C connected to chemical formula 2, one of the remaining Cs other than C connected to chemical formula 2 is C connected to chemical formula 3, and the remaining Cs are connected to chemical formula 4, or Among the above X1, X2 and X3, one is C connected to chemical formula 2, one of the remaining Cs other than C connected to chemical formula 2 is C connected to chemical formula 3, and the rest are C connected to chemical formula 4, [Chemical Formula 2] [Chemical Formula 3] [Chemical Formula 4] In the above chemical formulas 2 to 4, R1 to R4 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, One or both of Y1 to Y5 are N, and the rest are CRb, Rb is hydrogen; deuterium; or a substituted or unsubstituted alkyl group, Ar1 is a monocyclic or bicyclic, substituted or unsubstituted heteroarylene group having 2 to 20 carbon atoms, containing two Ns, Ar2 is hydrogen; deuterium; a substituted or unsubstituted alkyl group; or a substituted or unsubstituted aryl group, a and b are integers from 1 to 5, respectively, c and d are integers from 1 to 4, respectively, When a is 2 or more, R1 are equal or different, When b is 2 or more, R2 are equal or different, When c is 2 or more, R3 are equal or different, When d is 2 or more, R4 are equal or different, is the position connected to the above chemical formula 1.

2. In claim 1, the compound wherein the chemical formula 1 is any one of the following chemical formulas 1-1 to 1-6: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] In the above chemical formulas 1-1 to 1-6, R1 to R4, Ra, Y1 to Y5, Ar1, Ar2 and a to d are as defined in the above chemical formula 1, k is an integer from 1 to 3, and when k is 2 or greater, Ra are equal to or different from each other.

3. In claim 1, the compound wherein the chemical formula 1 is any one of the following chemical formulas 1-7 to 1-9: [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] In the above chemical formulas 1-7 to 1-9, R1 to R4, Ra, Y1 to Y5, Ar1, Ar2 and a to d are as defined in the above chemical formula 1, k is an integer from 1 to 3, and when k is 2 or greater, Ra are equal to or different from each other.

4. In claim 1, the compound wherein the chemical formula 4 is any one of the following chemical formulas 4-1 to 4-3: [Chemical Formula 4-1] [Chemical Formula 4-2] [Chemical Formula 4-3] In the above chemical formulas 4-1 to 4-3, R4 is hydrogen; or deuterium, One or both of Y1 to Y5 are N, and the rest are CRb, Rb is hydrogen; deuterium; or a substituted or unsubstituted alkyl group, d is an integer from 1 to 4, When d is 2 or more, R4 are equal or different, is the position connected to the above chemical formula 1.

5. A compound according to claim 1, wherein Ar1 is a substituted or unsubstituted divalent pyrimidinyl group; a substituted or unsubstituted divalent pyridazinyl group; a substituted or unsubstituted divalent imidazolyl group; a substituted or unsubstituted divalent pyrazolyl group; a substituted or unsubstituted divalent diazinyl group; a substituted or unsubstituted divalent pyrazinyl group; a substituted or unsubstituted divalent quinazolyl group; a substituted or unsubstituted divalent quinoxalyl group; or a substituted or unsubstituted divalent benzoimidazolyl group.

6. A compound according to claim 1, wherein each of R1 to R4 is hydrogen or deuterium.

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

8. 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 7.

9. An organic light-emitting device according to claim 8, 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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