Compound and organic light-emitting element comprising same

Abstract

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

Description

Compound and organic light-emitting device containing the same

[0001] This application claims the benefit of Korean Patent Application No. 10-2024-0001941, filed with the Korean Intellectual Property Office on January 5, 2024, the entire contents of which are incorporated herein by reference.

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

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

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

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

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

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

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

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

[0010] [Chemical Formula 1]

[0011]

[0012] In the above chemical formula 1,

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

[0014] R6 is hydrogen; deuterium; a nitrile group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group,

[0015] One or both of X1 to X5 are N, and the rest are CR',

[0016] R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group,

[0017] a and c are integers from 1 to 4, respectively,

[0018] b is an integer from 1 to 3,

[0019] d and e are each integers from 1 to 5,

[0020] f is 1 or 2,

[0021] When a is 2 or more, R1 are equal or different,

[0022] When b is 2 or more, R2 are equal or different,

[0023] When c is 2 or more, R3 are equal or different,

[0024] When d is 2 or more, R4 are equal or different,

[0025] When e is 2 or more, R5 are equal or different,

[0026] When f is 2, R6 are equal or different.

[0027] 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.

[0028] 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 or an electron injection and transport layer of an organic light-emitting device, the intramolecular polarization is high, thereby enhancing the effect of electron transfer, and thus an organic light-emitting device having long life characteristics can be manufactured.

[0029] The compound of the present invention exhibits high efficiency by maximizing electron mobility by limiting the substitution positions of the linking groups in the ortho direction instead of narrowing the distance between electron transport groups. In addition, the introduction of a heteroaryl group to the linker increases the steric hindrance of the molecule while appropriately breaking conjugation within the molecule, thereby maintaining long-life characteristics.

[0030] Figures 1 and 2 illustrate examples of organic light-emitting devices according to the present invention.

[0031] <Explanation of symbols>

[0032] 1: Substrate

[0033] 2: Anode

[0034] 3: Organic layer

[0035] 4: Cathode

[0036] 5: Hole injection layer

[0037] 6: Hole transport layer

[0038] 7: Electron blocking layer

[0039] 8: Emissive layer

[0040] 9: The hole-blocking layer

[0041] 10: Electron injection and transport layer

[0042] The following describes this specification in more detail.

[0043] 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.

[0044] 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.

[0045] Examples of substituents in this specification are described below, but are not limited thereto.

[0046] 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.

[0047] 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.

[0048] Examples of the above substituents are described below, but are not limited thereto.

[0049] In this specification, examples of halogen groups include fluorine (F), chlorine (Cl), bromine (Br), or iodine (I).

[0050] 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.

[0051] 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.

[0052] 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.

[0053] 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.

[0054] 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.

[0055] 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.

[0056] 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.

[0057] 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.

[0058] 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.

[0059] 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.

[0060] 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.

[0061] 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.

[0062] In this specification, the arylene group is as defined in the above aryl group, except that it is a divalent group.

[0063] In this specification, the heteroarylene group is as defined in the heteroaryl group above, except that it is divalent.

[0064] 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.

[0065] In this specification, the chemical formula 1 is any one of the compounds of the chemical formulas 1-1 to 1-10 below.

[0066] [Chemical Formula 1-1]

[0067]

[0068] [Chemical Formula 1-2]

[0069]

[0070] [Chemical Formula 1-3]

[0071]

[0072] [Chemical Formula 1-4]

[0073]

[0074] [Chemical Formula 1-5]

[0075]

[0076] [Chemical Formula 1-6]

[0077]

[0078] [Chemical Formula 1-7]

[0079]

[0080] [Chemical Formula 1-8]

[0081]

[0082] [Chemical Formula 1-9]

[0083]

[0084] [Chemical Formula 1-10]

[0085]

[0086] In the above chemical formulas 1-1 to 1-10, R1 to R6, X1 to X5 and a to f are as defined in the above chemical formula 1.

[0087] In one embodiment of the present invention, R1 to R3 of the chemical formulae 1-1 to 1-10 are compounds that are the same as or different from each other and are each independently hydrogen or deuterium.

[0088] In one embodiment of the present invention, the chemical formula 1 is any one of the compounds of the chemical formulas 1-1-1 to 1-1-10 below.

[0089] [Chemical Formula 1-1-1]

[0090]

[0091] [Chemical Formula 1-1-2]

[0092]

[0093] [Chemical Formula 1-1-3]

[0094]

[0095] [Chemical Formula 1-1-4]

[0096]

[0097] [Chemical Formula 1-1-5]

[0098]

[0099] [Chemical Formula 1-1-6]

[0100]

[0101] [Chemical Formula 1-1-7]

[0102]

[0103] [Chemical Formula 1-1-8]

[0104]

[0105] [Chemical Formula 1-1-9]

[0106]

[0107] [Chemical Formula 1-1-10]

[0108]

[0109] In the above chemical formulas 1-1-1 to 1-1-10, R4 to R6, X1 to X5, and d to f are as defined in the above chemical formula 1.

[0110] According to one embodiment of the present specification, R6 is hydrogen; deuterium; a nitrile group; a halogen group; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0111] According to one embodiment of the present specification, R6 is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.

[0112] According to one embodiment of the present specification, R6 is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.

[0113] According to one embodiment of the present specification, R6 is hydrogen; deuterium; a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms; or a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.

[0114] According to one embodiment of the present specification, R6 is hydrogen; deuterium; or an aryl group having 6 to 30 carbon atoms.

[0115] According to one embodiment of the present specification, R6 is hydrogen; deuterium; or an aryl group having 6 to 20 carbon atoms.

[0116] According to one embodiment of the present specification, R6 is hydrogen; deuterium; or an aryl group having 6 to 15 carbon atoms.

[0117] According to one embodiment of the present specification, R6 is hydrogen; deuterium; a methyl group; an ethyl group; a propyl group; an isopropyl group; a butyl group; a terbutyl group; a phenyl group; a biphenyl group; a naphthyl group; an anthracene group; or a phenanthrene group.

[0118] According to one embodiment of the present specification, R6 is hydrogen; deuterium; a methyl group; an ethyl group; a phenyl group; a biphenyl group; or a naphthyl group.

[0119] According to one embodiment of the present specification, R6 is a phenyl group.

[0120] According to one embodiment of the present specification, when f is 2, R6 is hydrogen; deuterium; a methyl group; an ethyl group; a phenyl group; a biphenyl group; or a naphthyl group.

[0121] According to one embodiment of the present specification, when f is 2, R6 is a phenyl group.

[0122] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently represent hydrogen; deuterium; a nitrile group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group.

[0123] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently represent hydrogen; deuterium; a nitrile group; a halogen group; a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms.

[0124] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently represent hydrogen; deuterium; a nitrile group; a halogen group; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0125] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently represent hydrogen; deuterium; a nitrile group; a halogen group; an alkyl group having 1 to 10 carbon atoms; an aryl group having 6 to 30 carbon atoms; or a heteroaryl group having 3 to 30 carbon atoms.

[0126] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently represent hydrogen; deuterium; a nitrile group; a halogen group; or an alkyl group having 1 to 10 carbon atoms.

[0127] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently, hydrogen; deuterium; nitrile group; F; Cl; Br; I; methyl group; ethyl group; propyl group; isopropyl group; butyl group; terbutyl group; phenyl group; naphthyl group; biphenyl group; terphenyl group; pyrrole group; furan group; thiophene group; triazine group; pyrimidine group; pyridine group; carbazole group; dibenzofuran group; or dibenzothiophene group.

[0128] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently represent hydrogen; deuterium; nitrile group; F; Cl; Br; I; methyl group; ethyl group; propyl group; isopropyl group; butyl group; phenyl group; naphthyl group or terbutyl group.

[0129] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently represent hydrogen; deuterium; a nitrile group; a halogen group; a phenyl group, or a naphthyl group.

[0130] According to one embodiment of the present specification, R1 to R5 are the same as or different from each other, and each independently represent hydrogen; deuterium; a phenyl group or a naphthyl group.

[0131] According to one embodiment of the present specification, each of R1 to R5 is hydrogen or deuterium.

[0132] According to one embodiment of the present specification, R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0133] According to one embodiment of the present specification, R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0134] According to one embodiment of the present specification, R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0135] According to one embodiment of the present specification, R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0136] According to one embodiment of the present specification, R' is hydrogen; deuterium; or a substituted or unsubstituted ethyl group or a substituted or unsubstituted methyl group.

[0137] According to one embodiment of the present specification, one or both of X1 to X5 are N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0138] According to one embodiment of the present specification, one of X1 to X5 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0139] According to one embodiment of the present specification, one of X1 to X5 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0140] According to one embodiment of the present specification, one of X1 to X5 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0141] According to one embodiment of the present specification, one of X1 to X5 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0142] According to one embodiment of the present specification, one of X1 to X5 is N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms.

[0143] According to one embodiment of the present specification, one of X1 to X5 is N, the others are CR', and R' is hydrogen; deuterium; or a methyl group.

[0144] According to one embodiment of the present specification, any two of X1 to X5 are N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0145] According to one embodiment of the present specification, any two of X1 to X5 are N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

[0146] According to one embodiment of the present specification, any two of X1 to X5 are N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms.

[0147] According to one embodiment of the present specification, any two of X1 to X5 are N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

[0148] According to one embodiment of the present specification, any two of X1 to X5 are N, the others are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms.

[0149] According to one embodiment of the present specification, any two of X1 to X5 are N, the others are CR', and R' is hydrogen; deuterium; or a methyl group.

[0150] According to one embodiment of the present specification, among X1 to X5, X1 is N, the rest are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0151] According to one embodiment of the present specification, among X1 to X5, X2 is N, the rest are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0152] According to one embodiment of the present specification, among X1 to X5, X3 is N, the rest are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0153] According to one embodiment of the present specification, among X1 to X5, X4 is N, the rest are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0154] According to one embodiment of the present specification, among X1 to X5, X5 is N, the rest are CR', and R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group.

[0155] According to one embodiment of the present specification, among X1 to X5, X1 is N, the rest are CR', and R' is hydrogen; deuterium; or a methyl group.

[0156] According to one embodiment of the present specification, among X1 to X5, X2 is N, the rest are CR', and R' is hydrogen; deuterium; or a methyl group.

[0157] According to one embodiment of the present specification, among X1 to X5, X3 is N, the rest are CR', and R' is hydrogen; deuterium; or a methyl group.

[0158] According to one embodiment of the present specification, among X1 to X5, X4 is N, the rest are CR', and R' is hydrogen; deuterium; or a methyl group.

[0159] According to one embodiment of the present specification, among X1 to X5, X5 is N, the rest are CR', and R' is hydrogen; deuterium; or a methyl group.

[0160] In one embodiment of the present specification, a is an integer from 1 to 4.

[0161] In one embodiment of the present specification, a is 4.

[0162] In one embodiment of the present specification, a is 3.

[0163] In one embodiment of the present specification, a is 2.

[0164] In one embodiment of the present specification, a is 1.

[0165] In one embodiment of the present specification, b is an integer from 1 to 3.

[0166] In one embodiment of the present specification, b is 3.

[0167] In one embodiment of the present specification, b is 2.

[0168] In one embodiment of the present specification, b is 1.

[0169] In one embodiment of the present specification, c is an integer from 1 to 4.

[0170] In one embodiment of the present specification, c is 4.

[0171] In one embodiment of the present specification, c is 3.

[0172] In one embodiment of the present specification, c is 2.

[0173] In one embodiment of the present specification, c is 1.

[0174] In one embodiment of the present specification, d is an integer from 1 to 5.

[0175] In one embodiment of the present specification, d is 5.

[0176] In one embodiment of the present specification, d is 4.

[0177] In one embodiment of the present specification, d is 3.

[0178] In one embodiment of the present specification, d is 2.

[0179] In one embodiment of the present specification, d is 1.

[0180] In one embodiment of the present specification, e is an integer from 1 to 5.

[0181] In one embodiment of the present specification, e is 5.

[0182] In one embodiment of the present specification, e is 4.

[0183] In one embodiment of the present specification, e is 3.

[0184] In one embodiment of the present specification, e is 2.

[0185] In one embodiment of the present specification, e is 1.

[0186] In one embodiment of the present specification, f is 1 or 2.

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

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

[0189] In one embodiment of the present specification, the chemical formula 1 is any one of the following compounds.

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201] The substituent of the compound of the above chemical formula 1 can be combined by a method known in the art, and the type, position or number of the substituent can be changed according to a technique known in the art.

[0202] 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.

[0203] In addition, an organic light-emitting device according to the present invention is an organic light-emitting device comprising a first electrode; a second electrode provided opposite the first electrode; and one or more organic layers provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises the above-described compound.

[0204] 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.

[0205] 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.

[0206] 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.

[0207] 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.

[0208] 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.

[0209] In the organic light-emitting device of the present invention, the electron injection and transport layer includes the compound of the chemical formula 1 and a metal complex.

[0210] 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.

[0211] 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.

[0212] In one embodiment of the present specification, the first electrode is an anode and the second electrode is a cathode.

[0213] According to another embodiment, the first electrode is a cathode and the second electrode is an anode.

[0214] (1) Anode / hole transport layer / light emitting layer / cathode

[0215] (2) Anode / hole injection layer / hole transport layer / light-emitting layer / cathode

[0216] (3) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / cathode

[0217] (4) Anode / hole transport layer / light-emitting layer / electron transport layer / cathode

[0218] (5) Anode / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0219] (6) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode

[0220] (7) Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0221] (8) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / cathode

[0222] (9) Anode / hole injection layer / hole buffer layer / hole transport layer / light-emitting layer / electron transport layer / electron injection layer / cathode

[0223] (10) Anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

[0224] (11) Anode / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0225] (12) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / cathode

[0226] (13) Anode / hole injection layer / hole transport layer / electron blocking layer / light emitting layer / electron transport layer / electron injection layer / cathode

[0227] (14) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / cathode

[0228] (15) Anode / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0229] (16) Anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron transport layer / cathode

[0230] (17) Anode / hole injection layer / hole transport layer / light-emitting layer / hole blocking layer / electron transport layer / electron injection layer / cathode

[0231] (18) Anode / hole injection layer / hole transport layer / electron blocking layer / light-emitting layer / hole blocking layer / electron injection and transport layer / cathode

[0232] 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.

[0233] Figure 1 illustrates the structure of an organic light-emitting device in which an anode (2), an organic layer (3), and a cathode (4) are sequentially laminated on a substrate (1). In this structure, the compound represented by the chemical formula 1 may be included in the organic layer (3).

[0234] Figure 1 illustrates the structure of an organic light-emitting device in which an anode (2), an organic layer (3), and a cathode (4) are sequentially laminated on a substrate (1). In this structure, the compound represented by the chemical formula 1 may be included in the organic layer (3).

[0235] FIG. 2 illustrates the structure of an organic light-emitting device in which an anode (2), a hole injection layer (5), a hole transport layer (6), an electron blocking layer (7), a light-emitting layer (8), 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).

[0236] 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.

[0237] 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.

[0238] The anode is an electrode that injects holes, and as the anode material, a material having a high work function is generally preferred so that holes can be smoothly injected into the organic layer. Specific examples of the anode material that can be used in the present invention include, but are not limited to, metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; and conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole, and polyaniline.

[0239] 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.

[0240] The above hole injection layer is a layer that facilitates the injection of holes from the anode to the light-emitting layer, and the hole injection material is a material that can well inject holes from the anode at a low voltage, and it is preferable that the HOMO (highest occupied molecular orbital) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include, but are not limited to, metal porphyrine, oligothiophene, arylamine series organic materials, hexanitrilehexaazatriphenylene series organic materials, quinacridone series organic materials, perylene series organic materials, anthraquinone, and polyaniline and polythiophene series conductive polymers. The thickness of the hole injection layer may be 1 to 150 nm. If the thickness of the hole injection layer is 1 nm or more, there is an advantage of being able to prevent the hole injection characteristics from being deteriorated, and if it is 150 nm or less, there is an advantage of being able to prevent the driving voltage from being increased to improve the movement of holes due to the thickness of the hole injection layer being too thick.

[0241] In the present specification, the hole injection layer may include a compound of the following chemical formula HI-1.

[0242] [Chemical formula HI-1]

[0243]

[0244] In the above chemical formula HI-1,

[0245] R315 to R317 are the same or different, and each independently represent one selected from the group consisting of hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and combinations thereof, or combine with adjacent groups to form a substituted or unsubstituted ring,

[0246] r315 is an integer from 1 to 5, and when r315 is 2 or more, 2 or more R315 are the same as or different from each other,

[0247] r316 is an integer from 1 to 5, and when r316 is 2 or more, two or more R316 are the same as or different from each other.

[0248] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a substituted or unsubstituted aryl group; a substituted or unsubstituted heteroaryl group; and a combination thereof.

[0249] According to one embodiment of the present specification, R317 is any one selected from the group consisting of a carbazole group; a phenyl group; a biphenyl group; and combinations thereof.

[0250] According to one embodiment of the present specification, R315 and R316 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group.

[0251] According to one embodiment of the present specification, R315 and R316 are phenyl groups.

[0252] According to one embodiment of the present specification, the chemical formula HI-1 is represented by the following compound.

[0253]

[0254] In one embodiment of the present specification, the hole injection layer includes a compound of the following chemical formula HI-2.

[0255] [Chemical formula HI-2]

[0256]

[0257] In the above chemical formula HI-2,

[0258] R111 to R113 are the same or different and are each independently hydrogen; a halogen group; a nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0259] a111 to a113 are integers from 1 to 5, respectively.

[0260] If a111 is 2 or more, 2 or more R11s are the same or different,

[0261] If a112 is 2 or more, 2 or more R112s are the same or different from each other,

[0262] If a113 is 2 or more, 2 or more R113s are the same or different.

[0263] In one embodiment of the present specification, R111 to R113 are the same as or different from each other, and are each a halogen group or a nitrile group.

[0264] In one embodiment of the present specification, R111 to R113 are the same as or different from each other, and are each fluorine; or a nitrile group.

[0265] In one embodiment of the present specification, the chemical formula HI-2 is represented by the following compound

[0266]

[0267] The above-mentioned hole transport layer can play a role in facilitating hole transport. A hole transport material capable of transporting holes from the anode or hole injection layer and transferring them to the light-emitting layer, and a material with high hole mobility is suitable. Specific examples include, but are not limited to, arylamine-based organic compounds, conductive polymers, and block copolymers with both conjugated and non-conjugated portions.

[0268] In one embodiment of the present specification, the hole transport layer includes, but is not limited to, a compound of the following chemical formula HT-1.

[0269] [Chemical formula HT-1]

[0270]

[0271] In the above chemical formula HT-1,

[0272] L201 and L202 are the same or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted arylene group,

[0273] R200 is a substituted or unsubstituted aryl group,

[0274] R201 to R204 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0275] In one embodiment of the present specification, L201 and L202 are the same as or different from each other, and each independently represents a substituted or unsubstituted arylene group.

[0276] In one embodiment of the present specification, L201 and L202 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0277] In one embodiment of the present specification, L201 and L202 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenylene group.

[0278] In one embodiment of the present specification, L201 and L202 are each a phenylene group.

[0279] In one embodiment of the present specification, R200 is a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group.

[0280] In one embodiment of the present specification, R200 is a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted pyrene group; or a substituted or unsubstituted fluorenyl group.

[0281] In one embodiment of the present specification, R200 is a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.

[0282] In one embodiment of the present specification, R201 to R204 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group.

[0283] In one embodiment of the present specification, R201 to R204 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group.

[0284] In one embodiment of the present specification, R201 to R204 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted pyrene group; or a substituted or unsubstituted fluorenyl group.

[0285] In one embodiment of the present specification, R201 to R204 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group.

[0286] In one embodiment of the present specification, each of R201 to R204 is a phenyl group.

[0287] In one embodiment of the present specification, the chemical formula HT-1 is represented by the following compound

[0288]

[0289] 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.

[0290] The above-mentioned light-emitting layer can emit red, green, or blue light, and can be made of a phosphorescent material or a fluorescent material. The above-mentioned light-emitting material is a material that can emit light in the visible light range by transporting holes and electrons from a hole transport layer and an electron transport layer, respectively, and combining them, and a material having good quantum efficiency for fluorescence or phosphorescence is preferable. Specific examples include, but are not limited to, 8-hydroxy-quinoline aluminum complex (Alq3); carbazole series compounds; dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compounds; benzoxazole, benzthiazole, and benzimidazole series compounds; poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds; polyfluorene, rubrene, etc.

[0291] 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.

[0292] 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.

[0293] [Chemical Formula H-1]

[0294]

[0295] In the above chemical formula H-1,

[0296] L301 and L302 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 heterocyclic group,

[0297] Ar301 and Ar302 are the same or different, and each independently represents hydrogen; deuterium; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,

[0298] R301 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,

[0299] r301 is an integer from 1 to 7, and when r301 is 2 or more, 2 or more R301 are equal to or different from each other.

[0300] In one embodiment of the present specification, L301 and L302 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group.

[0301] In one embodiment of the present specification, L301 and L302 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted phenylene group; a substituted or unsubstituted biphenylylene group; or a substituted or unsubstituted naphthylene group.

[0302] In one embodiment of the present specification, L301 and L302 are each direct bonds.

[0303] In one embodiment of the present specification, Ar301 and Ar302 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group.

[0304] In one embodiment of the present specification, Ar301 and Ar302 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group.

[0305] In one embodiment of the present specification, Ar301 and Ar302 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted pyrene group; or a substituted or unsubstituted fluorenyl group.

[0306] In one embodiment of the present specification, Ar301 and Ar302 are the same as or different from each other, and each independently represents a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted phenanthrene group.

[0307] In one embodiment of the present specification, Ar301 and Ar302 are the same as or different from each other, and are each independently a naphthyl group; or a phenanthrene group.

[0308] In one embodiment of the present specification, R301 is hydrogen.

[0309] In one embodiment of the present specification, the chemical formula H-1 is represented by the following compound.

[0310]

[0311] 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.

[0312] According to one embodiment of the present specification, the dopant includes, but is not limited to, a compound represented by the following chemical formula D-1.

[0313] [Chemical Formula D-1]

[0314]

[0315] In the above chemical formula D-1,

[0316] 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,

[0317] t3 and t4 are integers from 1 to 4, respectively.

[0318] t5 is an integer from 1 to 3,

[0319] If the above t3 is 2 or more, the above 2 or more T3 are the same or different from each other,

[0320] If the above t4 is 2 or more, the two or more T4 are the same or different from each other,

[0321] When the above t5 is 2 or more, the two or more T5 are the same or different from each other.

[0322] 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.

[0323] 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.

[0324] 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 tert-butyl group; or a phenyl group substituted or unsubstituted with a tert-butyl group.

[0325] According to one embodiment of the present specification, the chemical formula D-1 is represented by the following compound.

[0326]

[0327] The electron transport layer can play a role in facilitating electron transport. As the electron transport material, a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is suitable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The thickness of the electron transport layer may be 1 to 50 nm. When the thickness of the electron transport layer is 1 nm or more, there is an advantage in that the electron transport characteristics can be prevented from being deteriorated, and when the thickness of the electron transport layer is 50 nm or less, there is an advantage in that the driving voltage can be prevented from increasing to improve electron movement due to the electron transport layer being too thick.

[0328] 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.

[0329] 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.

[0330] The electron transport layer can play a role in facilitating electron transport. As the electron transport material, a material that can easily receive electrons from the cathode and transfer them to the light-emitting layer, and a material with high electron mobility is suitable. Specific examples include, but are not limited to, Al complexes of 8-hydroxyquinoline; complexes containing Alq3; organic radical compounds; and hydroxyflavone-metal complexes. The thickness of the electron transport layer may be 1 to 50 nm. When the thickness of the electron transport layer is 1 nm or more, there is an advantage in that the electron transport characteristics can be prevented from being deteriorated, and when the thickness of the electron transport layer is 50 nm or less, there is an advantage in that the driving voltage can be prevented from increasing to improve electron movement due to the electron transport layer being too thick.

[0331] 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.

[0332] 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.

[0333] 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.

[0334] 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.

[0335] 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.

[0336] 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.

[0337] A hole-blocking (electron-controlling) layer may be provided between the electron transport layer and the light-emitting layer, and the hole-blocking (electron-controlling) layer is a layer that blocks holes from the light-emitting layer from flowing into the cathode and controls electrons flowing into the light-emitting layer to control the performance of the entire device. As the hole-blocking (electron-controlling) material, a compound having the ability to prevent holes from flowing into the cathode from the light-emitting layer and to control electrons injected into the light-emitting layer or the light-emitting material is preferable. An appropriate material may be used as the hole-blocking (electron-controlling) material depending on the composition of the organic layer used in the device. Specifically, examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc.

[0338] In one embodiment of the present specification, the hole-blocking (electron-controlling) layer may include a compound having a structure in which an N-containing ring is directly connected to a spiro[fluorene-9,9'-xanthene] structure or through a linker.

[0339] In one embodiment of the present specification, the hole blocking layer includes a compound of the following chemical formula HB-1.

[0340] [Chemical formula HB-1]

[0341]

[0342] In the above chemical formula HB-1,

[0343] L501 to L503 are the same or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted arylene group,

[0344] R501 to R504 are the same or different, and each independently represent hydrogen; deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted amine group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group.

[0345] In one embodiment of the present specification, L501 and L502 are the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted naphthylene group.

[0346] In one embodiment of the present specification, L501 and L502 are the same as or different from each other, and each independently represents a direct bond; or a substituted or unsubstituted phenylene group.

[0347] In one embodiment of the present specification, L501 and L502 are the same as or different from each other, and are each independently a direct bond; or a phenylene group.

[0348] In one embodiment of the present specification, L503 is the same as or different from each other, and each independently represents a direct bond; a substituted or unsubstituted phenylene group; or a substituted or unsubstituted biphenylene group.

[0349] In one embodiment of the present specification, the L503 is the same as or different from each other, and each independently represents a direct bond; or a biphenylene group.

[0350] In one embodiment of the present specification, R501 and R502 are the same as or different from each other, and each independently represents a substituted or unsubstituted aryl group.

[0351] In one embodiment of the present specification, R501 and R502 are the same as or different from each other, and each independently represents a substituted or unsubstituted monocyclic aryl group; or a substituted or unsubstituted polycyclic aryl group.

[0352] In one embodiment of the present specification, R503 and R504 are the same as or different from each other, and each independently represents a substituted or unsubstituted alkyl group.

[0353] In one embodiment of the present specification, R501 to R504 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted naphthyl group; a substituted or unsubstituted anthracenyl group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted pyrene group; or a substituted or unsubstituted fluorenyl group.

[0354] In one embodiment of the present specification, R501 to R504 are the same as or different from each other, and each independently represents a substituted or unsubstituted phenyl group; or a substituted or unsubstituted naphthyl group.

[0355] In one embodiment of the present specification, R501 to R504 are the same as or different from each other, and each independently represents a phenyl group; or a naphthyl group.

[0356] In one embodiment of the present specification, the chemical formula HB-1 is represented by the following compound.

[0357]

[0358] 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.

[0359] The organic light-emitting device according to the present specification can be incorporated into and used in various electronic devices. For example, the electronic devices may be, but are not limited to, display panels, touch panels, solar modules, lighting devices, etc.

[0360] 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.

[0361] Hereinafter, the present specification will be described in detail with examples and comparative examples. However, the examples and comparative examples according to the present specification may be modified in various different forms, and the scope of the present specification is not construed as being limited to the examples and comparative examples described below. The examples and comparative examples of the present specification are provided to more fully explain the present specification to those with average knowledge in the art.

[0362] [Synthesis example]

[0363] Manufacturing Example 1. Synthesis of Chemical Formula E1

[0364]

[0365] The above compounds 6,6'-(2'-chloro-[1,1'-biphenyl]-2,4'-diyl)bis(2,4-diphenyl-1,3,5-triazine) (10.0 g, 15.4 mmol) and (3-(pyridin-3-yl)phenyl)boronic acid (3.06 g, 18.3 mmol) were completely dissolved in tetrahydrofuran (100 ml), and potassium carbonate (6.37, 46.1 mmol) dissolved in 19 ml of water was added, and the mixture was heated to reflux. To this, tetrakistriphenylphosphinepalladium (532 mg, 0.5 mmol) dissolved in tetrahydrofuran was slowly added. After lowering the temperature to room temperature and completing the reaction, the mixture was filtered to remove the potassium carbonate solution, and a filtered white solid was obtained. The filtered white solid was washed twice with water and ethyl acetate, respectively, to prepare the compound of the above chemical formula E1 (9.8 g, yield 83%).

[0366] MS[M+H] + = 770

[0367] Manufacturing Example 2. Chemical Formula E2

[0368]

[0369] A compound of the above chemical formula E2 was prepared in the same manner as in Manufacturing Example 1, except that (4-(pyridin-3-yl)phenyl)boronic acid was used instead of the above (3-(pyridin-3-yl)phenyl)boronic acid in Manufacturing Example 1.

[0370] MS[M+H] + = 770

[0371] Manufacturing Example 3. Synthesis of Chemical Formula E3

[0372]

[0373] A compound of the above chemical formula E3 was prepared in the same manner as in Preparation Example 2, except that 6,6'-(5'-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of 6,6'-(2'-chloro-[1,1'-biphenyl]-2,4'-diyl)bis(2,4-diphenyl-1,3,5-triazine).

[0374] MS[M+H] + = 770

[0375] Manufacturing Example 4. Synthesis of Chemical Formula E4

[0376]

[0377] A compound of the above chemical formula E4 was prepared in the same manner as in Preparation Example 3, except that (3-(pyridin-3-yl)phenyl)boronic acid was used instead of the compound (4-(pyridin-3-yl)phenyl)boronic acid in Preparation Example 3.

[0378] MS[M+H] + = 770

[0379] Manufacturing Example 5. Synthesis of Chemical Formula E5

[0380]

[0381] A compound of the chemical formula E5 was prepared in the same manner as in Preparation Example 4, except that 6,6'-(5-chloro-[1,1'-biphenyl]-2,2'-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of the compound 6,6'-(5'-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 4.

[0382] MS[M+H] + = 770

[0383] Manufacturing Example 6. Synthesis of Chemical Formula E6

[0384]

[0385] A compound of the chemical formula E6 was prepared in the same manner as in Preparation Example 5, except that 6,6'-(3'-chloro-[1,1'-biphenyl]-2,4'-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of the compound 6,6'-(5-chloro-[1,1'-biphenyl]-2,2'-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 5.

[0386] MS[M+H] + = 770

[0387] Manufacturing Example 7. Synthesis of Chemical Formula E7

[0388]

[0389] A compound of the chemical formula E7 was prepared in the same manner as in Preparation Example 6, except that 6,6'-(4'-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of 6,6'-(3'-chloro-[1,1'-biphenyl]-2,4'-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 6.

[0390] MS[M+H] + = 770

[0391] Manufacturing Example 8. Synthesis of Chemical Formula E8

[0392]

[0393] A compound of the chemical formula E8 was prepared in the same manner as in Preparation Example 7, except that 6,6'-(4-chloro-[1,1'-biphenyl]-2,2'-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of the compound 6,6'-(4'-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 7.

[0394] MS[M+H] + = 770

[0395] Manufacturing Example 9. Synthesis of Chemical Formula E9

[0396]

[0397] In Manufacturing Example 8, a compound of the above chemical formula E9 was manufactured in the same manner as Manufacturing Example 8, except that 6,6'-(6'-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of the compound 6,6'-(4-chloro-[1,1'-biphenyl]-2,2'-diyl)bis(2,4-diphenyl-1,3,5-triazine).

[0398] MS[M+H] + = 770

[0399] Manufacturing Example 10. Synthesis of Chemical Formula E10

[0400]

[0401] A compound of the chemical formula E10 was prepared in the same manner as in Preparation Example 9, except that 6,6'-(3-chloro-[1,1'-biphenyl]-2,2'-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of the compound 6,6'-(6'-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 9.

[0402] MS[M+H] + = 770

[0403] Manufacturing Example 11. Synthesis of Chemical Formula E11

[0404]

[0405] A compound of the chemical formula E11 was prepared in the same manner as in Preparation Example 10, except that 6,6'-(2'-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of the compound 6,6'-(3-chloro-[1,1'-biphenyl]-2,2'-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 10.

[0406] MS[M+H] + = 770

[0407] Manufacturing Example 12. Synthesis of Chemical Formula E12

[0408]

[0409] A compound of the chemical formula E12 was prepared in the same manner as in Preparation Example 11, except that 6,6'-(6-chloro-[1,1'-biphenyl]-2,2'-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of the compound 6,6'-(2'-chloro-[1,1'-biphenyl]-2,3'-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 11.

[0410] MS[M+H] + = 770

[0411] Manufacturing Example 13 Synthesis of Chemical Formula E13

[0412]

[0413] In Manufacturing Example 12, the compound of formula E13 was manufactured in the same manner as in Manufacturing Example 12, except that 2-(4-chloro-2'-(4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of the compound 6,6'-(6-chloro-[1,1'-biphenyl]-2,2'-diyl)bis(2,4-diphenyl-1,3,5-triazine).

[0414] MS[M+H] + = 820

[0415] Manufacturing Example 14 Synthesis of Chemical Formula E14

[0416]

[0417] In Manufacturing Example 13, the compound 2-(4-chloro-2'-(4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was replaced with 2-([1,1'-biphenyl]-2-yl)-4-(3'-chloro-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazine, and the compound of the chemical formula E14 was prepared in the same manner as in Manufacturing Example 13, except that 2-([1,1'-biphenyl]-2-yl)-4-(3'-chloro-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2-yl)-6-phenyl-1,3,5-triazine was used.

[0418] MS[M+H] + = 847

[0419] Manufacturing Example 15 Synthesis of Chemical Formula E15

[0420]

[0421] In Manufacturing Example 1, 2-(3'-chloro-2'-(4,6-diphenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-2,4'-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of the compound 6,6'-(2'-chloro-[1,1'-biphenyl]-2,4'-diyl)bis(2,4-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 the compound of the chemical formula E15 was prepared in the same manner as in Manufacturing Example 1.

[0422] MS[M+H] + = 820

[0423] Manufacturing Example 16 Synthesis of Chemical Formula E16

[0424]

[0425] In Manufacturing Example 1, 2-(4-chloro-2'-(4-(naphthalen-1-yl)-6-phenyl-1,3,5-triazin-2-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine was used instead of the compound 6,6'-(2'-chloro-[1,1'-biphenyl]-2,4'-diyl)bis(2,4-diphenyl-1,3,5-triazine), and (3-(2,6-dimethylpyridin-4-yl)phenyl)boronic acid was used instead of (3-(pyridin-3-yl)phenyl)boronic acid, and the compound of the chemical formula E16 was prepared in the same manner as in Manufacturing Example 1.

[0426] MS[M+H] + = 849

[0427] Manufacturing Example 17 Synthesis of Chemical Formula E17

[0428]

[0429] The compound of the above chemical formula E17 was prepared in the same manner as in Preparation Example 5, except that (2-(pyridin-3-yl)phenyl)boronic acid was used instead of the compound (3-(pyridin-3-yl)phenyl)boronic acid in Preparation Example 5.

[0430] MS[M+H] + = 770

[0431] Manufacturing Example 18 Synthesis of Chemical Formula E18

[0432]

[0433] A compound of the chemical formula E18 was prepared in the same manner as in Preparation Example 6, except that (3-(pyridin-4-yl)phenyl)boronic acid was used instead of the compound (3-(pyridin-3-yl)phenyl)boronic acid in Preparation Example 6.

[0434] MS[M+H] + = 770

[0435] Manufacturing Example 19 Synthesis of Chemical Formula E19

[0436]

[0437] A compound of the chemical formula E19 was prepared in the same manner as in Preparation Example 7, except that (3-(pyridin-2-yl)phenyl)boronic acid was used instead of the compound (3-(pyridin-3-yl)phenyl)boronic acid in Preparation Example 7.

[0438] MS[M+H] + = 770

[0439] Manufacturing Example 20 Synthesis of Chemical Formula E20

[0440]

[0441] A compound of the chemical formula E20 was prepared in the same manner as in Manufacturing Example 9, except that (3-(pyridin-4-yl)phenyl)boronic acid was used instead of the compound (3-(pyridin-3-yl)phenyl)boronic acid in Manufacturing Example 9.

[0442] MS[M+H] + = 770

[0443] Manufacturing Example 21 Synthesis of Chemical Formula E21

[0444]

[0445] A compound of the above chemical formula E21 was prepared in the same manner as in Preparation Example 9, except that (3-(pyridin-2-yl)phenyl)boronic acid was used instead of the compound (3-(pyridin-3-yl)phenyl)boronic acid in Preparation Example 9.

[0446] MS[M+H] + = 770

[0447] Manufacturing Example 22 Synthesis of Chemical Formula E22

[0448]

[0449] A compound of the chemical formula E22 was prepared in the same manner as in Preparation Example 9, except that (4-(pyridin-3-yl)phenyl)boronic acid was used instead of the compound (3-(pyridin-3-yl)phenyl)boronic acid in Preparation Example 9.

[0450] MS[M+H]+ = 770

[0451] Manufacturing Example 23 Synthesis of Chemical Formula E23

[0452]

[0453] A compound of the chemical formula E23 was prepared in the same manner as in Preparation Example 6, except that (4-(pyridin-3-yl)phenyl)boronic acid was used instead of the compound (3-(pyridin-3-yl)phenyl)boronic acid in Preparation Example 6.

[0454] MS[M+H] + = 770

[0455] Manufacturing Example 24 Synthesis of Chemical Formula E24

[0456]

[0457] A compound of the chemical formula E24 was prepared in the same manner as in Manufacturing Example 6, except that (4-(pyridin-4-yl)phenyl)boronic acid was used instead of the compound (3-(pyridin-3-yl)phenyl)boronic acid in Manufacturing Example 6.

[0458] MS[M+H] + = 770

[0459] Manufacturing Example 25. Synthesis of Chemical Formula E25

[0460]

[0461] A compound of the chemical formula E25 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 compound (3-(pyridin-3-yl)phenyl)boronic acid in Manufacturing Example 1.

[0462] MS[M+H] + = 770

[0463] Manufacturing Example 26. Synthesis of Chemical Formula E26

[0464]

[0465] A compound of the chemical formula E26 was prepared in the same manner as in Manufacturing Example 1, except that (3-(pyridin-2-yl)phenyl)boronic acid was used instead of the compound (3-(pyridin-3-yl)phenyl)boronic acid in Manufacturing Example 1.

[0466] MS[M+H] + = 770

[0467] Manufacturing Example 27. Synthesis of Chemical Formula E27

[0468]

[0469] A compound of the chemical formula E27 was prepared in the same manner as in Preparation Example 1, except that 2-(3'-(4,6-bis(phenyl-d5)-1,3,5-triazin-2-yl)-5'-chloro-[1,1'-biphenyl]-2-yl)-4,6-diphenyl-1,3,5-triazine was used instead of the compound 6,6'-(2'-chloro-[1,1'-biphenyl]-2,4'-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 1.

[0470] MS[M+H] + = 780

[0471] Manufacturing Example 28. Synthesis of Chemical Formula E28

[0472]

[0473] A compound of the chemical formula E28 was prepared in the same manner as in Preparation Example 1, except that 2-(4'-(4,6-bis(phenyl-d5)-1,3,5-triazin-2-yl)-2'-chloro-[1,1'-biphenyl]-2,4'-diyl)bis(2,4-diphenyl-1,3,5-triazine) was used instead of the compound 6,6'-(2'-chloro-[1,1'-biphenyl]-2,4'-diyl)bis(2,4-diphenyl-1,3,5-triazine) in Preparation Example 1.

[0474] MS[M+H] + = 780

[0475] [Example]

[0476] Example 1-1

[0477] 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.

[0478] On the anode, which is an 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 hole transport layer was formed by vacuum depositing a compound represented by the chemical formula HT1 (1150 Å). Subsequently, an electron blocking layer was formed by vacuum depositing a compound EB1 at a film thickness of 50 Å on the hole transport layer. 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 at 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.

[0479]

[0480] 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 2×10 -7 ~ 5×10 -6 Torr was maintained, and an organic light-emitting device was fabricated.

[0481] Examples 1-2 to 1-28

[0482] 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 of Example 1.

[0483] Comparative Examples 1-1 to 1-4

[0484] 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 ET-1, ET-2, ET-3, and ET-4 used in Table 1 below are as follows.

[0485]

[0486] When current was applied to the organic light-emitting devices manufactured by Examples 1-1 to 1-28 and Comparative Examples 1-1 to 1-4, 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%.

[0487] Compound (electron transport layer) voltage (V@20mA / cm 2 )Efficiency (cd / A@20mA / cm 2 )Color coordinates (x,y)T95(hr) @20mA / cm 2Example 1-1 Compound E14.2 16.01 (0.139, 0.040) 242 Example 1-2 Compound E24.3 4 6.02 (0.138, 0.040) 240 Example 1-3 Compound E34.4 0 6.11 (0.139, 0.039) 245 Example 1-4 Compound E44.2 5 6.12 (0.140, 0.039) 260 Example 1-5 Compound E54.2 3 6.22 (0.139, 0.040) 258 Example 1-6 Compound E64.3 2 6.26 (0.140, 0.040) 259 Example 1-7 Compound E74.336.41(0.139, 0.039)248 Example 1-8 Compound E84.356.29(0.138, 0.040)251 Example 1-9 Compound E94.256.33(0.139, 0.040)250 Example 1-10 Compound E104.346.32(0.140, 0.039)247 Example 1-11 Compound E114.356.21(0.139, 0.039)246 Example 1-12 Compound E124.326.22(0.140, 0.039)251 Example 1-13 Compound E134.3 16.24 (0.139, 0.039) 248 Example 1-14 Compound E144.25 6.29 (0.140, 0.039) 243 Example 1-15 Compound E154.37 6.23 (0.139, 0.039) 236 Example 1-16 Compound E164.42 6.34 (0.140, 0.040) 238 Example 1-17 Compound E174.41 6.32 (0.139, 0.039) 235 Example 1-18 Compound E184.40 6.30 (0.139, 0.040) 232 Example 1-19 Compound E194.376.29(0.139, 0.039)234 Example 1-20 Compound E204.326.35(0.139, 0.040)235 Example 1-21 Compound E214.316.33(0.138, 0.040)232 Example 1-22 Compound E224.396.35(0.140, 0.040)237 Example 1-23 Compound E234.406.30(0.139, 0.040)238 Example 1-24 Compound E244.326.27(0.139, 0.039)242 Example 1-25 Compound E254.306.36(0.138, 0.040)234Example 1-26Compound E264.336.30(0.139, 0.039)238Example 1-27Compound E274.456.31(0.139, 0.039)243Example 1-28Compound E284.316.25(0.141, 0.040)249Comparative Example 1-1ET-14.745.40(0.140, 0.039)187Comparative Example 1-2ET-24.625.56(0.139, 0.040)179Comparative Example 1-3ET-34.785.11(0.139, 0.040)146Comparative Example 1-4ET-44.815.24(0.139, 0.040)172.

[0488] As shown in Table 1 above, in the case of an organic light-emitting device manufactured using the compound of the present invention as an electron transport layer or an electron injection and transport layer, the organic light-emitting device exhibits excellent characteristics in terms of efficiency, driving voltage, and / or stability.

[0489] Compared to the electron transport layer generally used, the present invention appropriately sets the distance between N-containing ring groups and limits the direction of the linker connecting them to ortho to appropriately break the conjugation, thereby controlling electron injection and mobility, thereby exhibiting low-voltage, high-efficiency characteristics.

[0490] Although the preferred embodiment (electron injection and transport layer) of the present invention has been described above, the present invention is not limited thereto, and various modifications can be made within the scope of the claims and the detailed description of the invention, and this also falls within the scope of the invention.

Claims

1. A compound of the following chemical formula 1: [Chemical Formula 1] In the above chemical formula 1, R1 to R5 are the same as or different from each other, and each independently represent hydrogen; deuterium; a nitrile group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, R6 is hydrogen; deuterium; a nitrile group; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group, One or both of X1 to X5 are N, and the rest are CR', R' is hydrogen; deuterium; or a substituted or unsubstituted alkyl group, a and c are integers from 1 to 4, respectively, b is an integer from 1 to 3, d and e are each integers from 1 to 5, f is 1 or 2, When a is 2 or more, R1 is equal to or different from each other, When b is 2 or more, R2 are equal or different, When c is 2 or greater, R3 are equal or different, When d is 2 or more, R4 are equal or different, When e is 2 or greater, R5 are equal or different, When f is 2, R6 are equal or different.

2. In claim 1, the chemical formula 1 is a compound which is any one of the following chemical formulas 1-1 to 1-10: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formula 1-3] [Chemical Formula 1-4] [Chemical Formula 1-5] [Chemical Formula 1-6] [Chemical Formula 1-7] [Chemical Formula 1-8] [Chemical Formula 1-9] [Chemical Formula 1-10] In the chemical formulas 1-1 to 1-10 above, R1 to R6, X1 to X5, and a to f are as defined in the chemical formula 1 above.

3. A compound according to claim 2, wherein R1 to R3 in chemical formulae 1-1 to 1-10 are the same as or different from each other and are each independently hydrogen or deuterium.

4. In claim 1, the chemical formula 1 is a compound which is any one of the following chemical formulas 1-1-1 to 1-1-10: [Chemical Formula 1-1-1] [Chemical Formula 1-1-2] [Chemical Formula 1-1-3] [Chemical Formula 1-1-4] [Chemical Formula 1-1-5] [Chemical Formula 1-1-6] [Chemical Formula 1-1-7] [Chemical Formula 1-1-8] [Chemical Formula 1-1-9] [Chemical Formula 1-1-10] In the chemical formulas 1-1-1 to 1-1-10, R4 to R6, X1 to X5, and d to f are as defined in the chemical formula 1.

5. A compound according to claim 1, wherein R6 is an aryl group having 6 to 30 carbon atoms.

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

7. In claim 1, the chemical formula 1 is a compound having 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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